CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2021-0174018, filed on Dec. 7, 2021, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.

BACKGROUND
1. Field

Provided are a heterocyclic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emissive devices that, as compared with devices in the art, have wide viewing angles, high contrast ratios, short response times, and excellent brightness, driving voltage, and response speed characteristics, and produce full-color images.

OLEDs include an anode, a cathode, and an organic layer between the anode and the cathode and including an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light.

SUMMARY

Provided are a heterocyclic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.

Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.

According to one or more embodiments, provided is a heterocyclic compound represented by Formula 1 below.

[Image Omitted]

In Formula 1,

A₁₁to A₁₅are each independently a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

X₁₁is N or B,

Y₁₁is a group represented by Formula 2-1 or a group represented by Formula 2-2, and m11 is 1, 2, 3, or 4,

[Image Omitted]

wherein, in Formulae 2-1 and 2-2,

X₂₁is a single bond, O, S, N(R₂₅), or C(R₂₅)(R₂₆),

L₂₁and L₂₂are each independently a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a21 and a22 are each independently 0, 1, or 2,

R₂₁and R₂₂are each independently a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

Z₁₁to Z₁₄are each independently a group represented by Formula 2-3, and n11 to n14 are each independently 0, 1, 2, 3, or 4, wherein the sum of n11 to n14 is 2 or more,

[Image Omitted]

wherein, in Formula 2-3, L₂₃is a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a23 may be 0, 1, or 2,

R₁₁to R₁₅and R₂₃to R₂₉may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀alkyl heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), or —P(═S)(Q₁)(Q₂),

b11 to b16 are each independently 0, 1, 2, or 3,

b23 and b24 are each independently 0, 1, 2, 3, or 4,

b27 to b29 are each independently 0, 1, 2, 3, 4, or 5,

Q₁to Q₃are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, and a C₆-C₆₀aryl group, and a C₆-C₆₀aryl group substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, or a C₆-C₆₀aryl group, and

* indicates a binding site to a neighboring atom.

According to one or more embodiments, provided is an organic light-emitting device including a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode and including an emission layer.

According to one or more embodiments, provided is an electronic apparatus including the organic light-emitting device.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:

FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 1 according to an exemplary embodiment;

FIG. 2 is a schematic cross-sectional view of an organic light-emitting device 100 according to another exemplary embodiment;

FIG. 3 is a schematic cross-sectional view of an organic light-emitting device 200 according to another exemplary embodiment;

FIG. 4A shows the general energy transfer for the First Embodiment;

FIG. 4B shows the general energy transfer for the Second Embodiment;

FIG. 4C shows the general energy transfer for the Third Embodiment;

FIG. 4D shows the general energy transfer for the Fourth Embodiment; and

FIG. 4E shows the general energy transfer for the Fifth Embodiment.

DETAILED DESCRIPTION

Reference will now be made In an embodiment to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present

It will be understood that, although the terms “first,” “second,” “third” etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.

“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the Figures. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures. For example, if the device in one of the figures is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements. The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the figure. Similarly, if the device in one of the figures is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements. The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.

“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10% or 5% of the stated value.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

A heterocyclic Compound may be represented by Formula 1 below:

[Image Omitted]

wherein, in Formula 1, A₁₁to A₁₅may each independently be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group.

In an embodiment, in Formula 1, A₁₁to A₁₅may each independently be a benzene group, a naphthalene group, a phenanthrene group, a furan group, a thiophene group, a pyrrole group, a cyclopentene group, a silole group, a germole group, a benzofuran group, a benzothiophene group, an indole group, an indene group, a benzosilole group, a benzogermole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, or a dibenzogermole group.

In an embodiment, in Formula 1, A₁₁to A₁₅may each independently be a benzene group, a naphthalene group, a benzofuran group, a benzothiophene group, an indole group, an indene group, a benzosilole group, or a benzogermole group.

In an embodiment, in Formula 1, A₁₁to A₁₅may each independently be a benzene group or a naphthalene group.

In an embodiment, in Formula 1, A₁₁to A₁₅may each independently be a benzene group.

In Formula 1, X₁₁is N or B.

In an embodiment, in Formula 1, X₁₁may be B.

In Formula 1, Y₁₁may be a group represented by Formula 2-1 below or a group represented by Formula 2-2 below:

[Image Omitted]

wherein, in Formulae 2-1 and 2-2,

X₂₁may be a single bond, O, S, N(R₂₅), or C(R₂₅)(R₂₆),

L₂₁and L₂₂may each independently be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a21 and a22 may each independently be 0, 1, or 2,

R₂₁and R₂₂may each independently be a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

R₂₃to R₂₆may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀alkyl heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), or —P(═S)(Q₁)(Q₂),

Q₁to Q₃may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof, or a C₆-C₆₀aryl group substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof, b23 and b24 may each independently be 0, 1, 2, 3, or 4, and

* indicates a binding site to a neighboring atom.

In an embodiment, in Formulae 2-11 and 2-21, X₂₁may be a single bond.

In an embodiment, in Formulae 2-11 and 2-21, L₂₁and L₂₂may each independently be a substituted or unsubstituted C₅-C₃₀carbocyclic group.

In an embodiment, in Formulae 2-11 and 2-21, L₂₁and L₂₂may each independently be a benzene group.

In an embodiment, in Formulae 2-11 and 2-21, a21 and a22 may each independently be 0 or 1.

In an embodiment, in Formulae 2-11 and 2-21, R₂₁and R₂₂may each independently be a C₁-C₂₀alkyl group that is unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a deuterated C₂-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.1]heptyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —Ge(Q₁₁)(Q₁₂)(Q₁₃), —C(Q₁₁)(Q₁₂)(Q₁₃), —B(Q₁₁)(Q₁₂), —N(Q₁₁)(Q₁₂), —P(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), —P(═S)(Q₁₁)(Q₁₂), or any combination thereof; or

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a deuterated C₂-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.1]heptyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —Ge(Q₂₁)(Q₂₂)(Q₂₃), —C(Q₂₁)(Q₂₂)(Q₂₃), —B(Q₂₁)(Q₂₂), —N(Q₂₁)(Q₂₂), —P(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), —P(═S)(Q₂₁)(Q₂₂), or any combination thereof, and

Q₁₁to Q₁₃and Q₂₁to Q₂₃may each independently be: deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, —CD₂CDH₂, —CF₃, —CF₂H, —CFH₂, —CH₂CF₃, —CH₂CF₂H, —CH₂CFH₂, —CHFCH₃, —CHFCF₂H, —CHFCFH₂, —CHFCF₃, —CF₂CF₃, —CF₂CF₂H, or —CF₂CFH₂, or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, a C₁-C₁₀alkyl group, a deuterated C₁-C₁₀alkyl group, a phenyl group, or any combination thereof.

In an embodiment, in Formulae 2-11 and 2-21, R₂₁and R₂₂may each independently be a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, or a dibenzocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a deuterated C₂-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.1]heptyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or any combination thereof.

In an embodiment, in Formulae 2-11 and 2-21, R₂₁and R₂₂may each independently be —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a group represented by one of Formulae 10-12 to 10-23, 10-38 to 10-130, and 10-238 to 10-272 below, a group in which at least one hydrogen in Formulae 10-12 to 10-23, 10-38 to 10-130, and 10-238 to 10-272 below is substituted with deuterium, a group in which at least one hydrogen in Formulae 10-12 to 10-23, 10-38 to 10-130, and 10-238 to 10-272 below is substituted with —F:

[Image Omitted]

In an embodiment, in Formulae 2-11 and 2-21, R₂₃to R₂₆may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, a C₁-C₂₀alkyl group, a C₁-C₂₀alkenyl group, a C₁-C₂₀alkoxy group, or a C₁-C₂₀alkylthio group;

a C₁-C₂₀alkyl group, a C₁-C₂₀alkenyl group, a C₁-C₂₀alkoxy group, or a C₁-C₂₀alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.1]heptyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a deuterated C₂-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.1]heptyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof; or

—Si(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), or —N(Q₁)(Q₂),

wherein Q₁to Q₃may be each independently:

deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, —CD₂CDH₂, —CF₃, —CF₂H, —CFH₂, —CH₂CF₃, —CH₂CF₂H, —CH₂CFH₂, —CHFCH₃, —CHFCF₂H, —CHFCFH₂, —CHFCF₃, —CF₂CF₃, —CF₂CF₂H, or —CF₂CFH₂; or

an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, a C₁-C₁₀alkyl group, a phenyl group, or any combination thereof.

In an embodiment, in Formulae 2-11 and 2-21, R₂₃to R₂₆may each independently be hydrogen, deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₂-C₁₀alkenyl group, a C₁-C₁₀alkoxy group, a C₁-C₁₀alkylthio group, a group represented by one of Formulae 9-1 to 9-39 below, a group in which at least one hydrogen in Formulae 9-1 to 9-39 below is substituted with deuterium, a group in which at least one hydrogen in Formulae 9-1 to 9-39 below is substituted with —F, a group represented by one of Formulae 9-201 to 9-236 below, a group in which at least one hydrogen in Formulae 9-201 to 9-236 below is substituted with deuterium, a group in which at least one hydrogen in Formulae 9-201 to 9-236 below is substituted with —F, a group represented by one of Formulae 10-1 to 10-130 below, a group in which at least one hydrogen in Formulae 10-1 to 10-130 below is substituted with deuterium, a group in which at least one hydrogen in Formulae 10-1 to 10-130 below is substituted with —F, a group represented by one of Formulae 10-201 to 10-358 below, a group in which at least one hydrogen in Formulae 10-201 to 10-358 below is substituted with deuterium, a group in which at least one hydrogen in Formulae 10-201 to 10-358 below is substituted with —F, —Si(Q₁)(Q₂)(Q₃), or —C(Q₁)(Q₂)(Q₃),

wherein Q₁to Q₃may be each independently:

deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, —CD₂CDH₂, —CF₃, —CF₂H, —CFH₂, —CH₂CF₃, —CH₂CF₂H, —CH₂CFH₂, —CHFCH₃, —CHFCF₂H, —CHFCFH₂, —CHFCF₃, —CF₂CF₃, —CF₂CF₂H, or —CF₂CFH₂, or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, a C₁-C₁₀alkyl group, a phenyl group, or any combination thereof.

[Image Omitted]

[Image Omitted]

In Formulae 9-1 to 9-39, 9-201 to 9-236, 10-1 to 10-130, and 10-201 to 10-358, * indicates a binding site to an adjacent atom, “Ph” represents a phenyl group, “TMS” and “SiMe₃” each represent a trimethylsilyl group, and “TMG” and “GeMe₃” each represent a trimethylgermyl group.

The “group represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by Formulae 9-201 to 9-236 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:

[Image Omitted]

The “group represented by Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by Formulae 9-201 to 9-236 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 9-701 to 9-710:

[Image Omitted]

The “group represented by Formulae 10-1 to 10-130 in which at least one hydrogen is substituted with a deuterium” and the “group represented by Formulae 10-201 to 10-358 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 10-501 to 10-576:

[Image Omitted]

The “group represented by Formulae 10-1 to 10-130 in which at least one hydrogen is substituted with —F” and the “group represented by Formulae 10-201 to 10-358 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 10-601 to 10-617:

[Image Omitted]

In an embodiment, in Formula 1, Y₁₁may be a group represented by Formula 2-2. In an embodiment, in Formula 1, Y₁₁may be a group represented by Formula 2-11 below or a group represented by Formula 2-21:

[Image Omitted]

wherein, in Formulae 2-11 and 2-21,

L₂₁and L₂₂are respectively the same as described in connection with Formula 2-1,

a21 and a22 may each independently be 0 or 1,

R₂₀₁to R₂₁₈may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and

two neighboring groups R₂₀₁to R₂₀₅and/or two neighboring groups R₂₀₆to R₂₁₀may optionally form a ring.

In an embodiment, in Formula 1, Y₁₁may be a group represented by Formula 2-21.

In Formula 1, m11 may be 1, 2, 3, or 4. m11 indicates the number of substitution of Y₁₁.

In an embodiment, in Formula 1, m11 may be 1 or 2.

In Formula 1, Z₁₁to Z₁₄may each independently be a group represented by Formula 2-3 below:

[Image Omitted]

wherein, in Formula 2-3, L₂₃is the same as described in connection with L₂₁, a23 is the same as described in connection with a21, and R₂₇to R₂₉are respectively the same as described in connection with R₂₃,

b27 to b29 may each independently be 0, 1, 2, 3, 4, or 5, and

* indicates a binding site to a neighboring atom.

In Formula 1, n11 to n14 may each independently be 0, 1, 2, 3, or 4, wherein the sum of n11 to n14 is 2 or more. In Formula 1, n11 to n14 may each indicate the number of substitution of Y₁₁to Y₁₄.

In an embodiment, in Formula 1, the sum of n11 to n14 may be 2, 3, or 4.

In an embodiment, in Formula 1, the sum of n11 to n14 may be 2 or 3.

In Formula 1, R₁₁to R₁₅are respectively the same as described in connection with R₂₃.

In Formula 1, b11 to b16 may each independently be 0, 1, 2, or 3. In Formula 1, b11 to b16 may respectively indicate the number of substitution of R₁₁to R₁₆.

In an embodiment, the heterocyclic compound may be represented by Formula 1-1:

[Image Omitted]

wherein, in Formulae 1-111 and 1-211,

wherein, in Formula 1-1,

R₁₁₁to R₁₁₅may each independently be Z₁₁or R₁₁,

R₁₂₁to R₁₂₄may each independently be Z₁₂or R₁₂,

R₁₃₁to R₁₃₄may each independently be Z₁₃or R₁₃,

R₁₄₁to R₁₄₅may each independently be Z₁₄or R₁₄,

R₁₅₁to R₁₅₃may each independently be Y₁₁or R₁₅,

at least one of R₁₅₁to R₁₅₃may be Y₁₁,

at least two of R₁₁₁to R₁₁₅, R₁₂₁to R₁₂₄, R₁₃₁to R₁₃₄, and R₁₄₁to R₁₄₅may independently be Z₁₁, Z₁₂, Z₁₃, or Z₁₄, and

Y₁₁, Z₁₁to Z₁₄, and R₁₁to R₁₅are respectively the same as described in connection with Formula 1.

In an embodiment, the heterocyclic compound may be represented by one of Formulae 1-11 to 1-18:

[Image Omitted]

wherein, in Formulae 1-11 to 1-18,

A₁₁to A₁₅, Y₁₁, Z₁₁to Z₁₄, R₁₁to R₁₅, and b11 to b15 are respectively the same as described in connection with Formula 1,

m11 may be 1 or 2, and

n11 to n14 may each independently be 1 or 2, and in Formulae 1-11 and 1-12, n11 and n12 may each independently be 2.

In an embodiment, in Formulae 1-11 to 1-18, A₁₁to A₁₅may each be a benzene group.

In an embodiment, in Formulae 1-11 to 1-18, the sum of n11 to n14 may be 2, 3, or 4.

In an embodiment, the heterocyclic compound may be compounds of Group C, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

Since the heterocyclic compound has a rigid structure in which aromatic hydrocarbon rings or heteroaromatic rings are condensed, structural relaxation in an excited state may be suppressed. As a result, the heterocyclic compound may have a narrow width of blue emission spectrum and improved colorimetric purity.

When A₁₅is substituted with Y₁₁, a lowest excitation singlet energy level of the heterocyclic compound may be relatively increased, and accordingly, the heterocyclic compound may emit deep blue of high color purity. Also, when A₁₅is substituted with Y₁₁, a highest occupied molecular orbital (HOMO) energy level of the heterocyclic compound may be relatively decreased, and due to reduction in hole trapping properties, the efficiency of the organic light-emitting device including the heterocyclic compound may be improved.

Because the heterocyclic compound includes a group represented by Formula 2-3, Dexter energy transfer is inhibited due to its relatively high steric hindrance, and thus, the efficiency of the organic light-emitting device including the heterocyclic compound may be improved.

Especially, in the heterocyclic compound, A₁₁to A₁₄are substituted with two or more groups represented by Formula 2-3, and thus, Dexter energy transfer may be effectively inhibited due to increased steric hindrance.

The peak wavelength in photoluminescence (PL) of the heterocyclic compound according to an embodiment is not particularly limited and may be about 430 nm or greater. In an embodiment, the peak wavelength may be in a range of about 435 nm or more, about 450 nm or more, about 490 nm or less, or about 470 nm or less. When the peak wavelength is within any of these ranges, the heterocyclic compound according to an embodiment may be more suitable for blue light emission.

The heterocyclic compound according to one or more embodiments may have a narrow full width at half maximum (FWHM) of an emission intensity of a peak having a PL peak wavelength. In an embodiment, FWHM may be about 45 nm or less, about 40 nm or less, or about 35 nm or less. When the FWHM is within any of these ranges, the heterocyclic compound according to an embodiment may have improved colorimetric purity.

The peak wavelength at PL and the FWHM at PL may be measured and/or calculated using a spectrofluorophotometer.

A HOMO energy level, lowest unoccupied molecular orbital (LUMO) energy level, S₁energy level, and T₁energy level of some heterocyclic compounds represented by Formula 1 and comparative compounds were evaluated using the Gaussian 09 program with the molecular structure optimization obtained by B3LYP-based density functional theory (DFT), and results thereof are shown in Table 1.

TABLE 1

Compound No.
HOMO (eV)
LUMO (eV)
S₁(eV)
T1(eV)

619
−5.00
−1.45
3.01
2.58

620
−4.99
−1.45
3.00
2.58

126
−4.97
−1.27
3.14
2.69

142
−4.93
−1.32
3.06
2.63

83
−4.90
−1.35
3.01
2.58

A
−4.76
−1.19
2.99
2.57

[Image Omitted]

Table 1 shows that the heterocyclic compound represented by Formula 1 has electric characteristics suitable for use in an electronic device, for example, a dopant in an emission layer of an organic light-emitting device.

The synthesis method of the heterocyclic compound according to one or more embodiments is not particularly limited and may be synthesized according to any known synthesis method. In particular, it may be synthesized according to or in view of the methods described in the Examples. For example, in the methods described in the Examples, the heterocyclic compound according to one or more embodiments may be synthesized through modifications such as changing raw materials and reaction conditions, adding or excluding some processes, or appropriately combining with other known synthesis methods.

The method of identifying a structure of the heterocyclic compound according to one or more embodiments is not particularly limited. The heterocyclic compound containing nitrogen according to one or more embodiments may be identified by a known method, for example, NMR or LC-MS.

Description of FIG. 1

FIG. 1 is a schematic view of an organic light-emitting device 10 according to an exemplary embodiment. Hereinafter a structure and a method of manufacturing the organic light-emitting device 10, according to an embodiment, will be described with reference to FIG. 1.

In FIG. 1, an organic light-emitting device 10 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an organic layer 10A between the first electrode 11 and the second electrode 19.

In FIG. 1, the organic layer 10A includes an emission layer 15, a hole transport region 12 is between the first electrode 11 and an emission layer 15, and an electron transport region 17 is between the emission layer 15 and the second electrode 19.

A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.

First Electrode 11

The first electrode 11 may be produced by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be materials with a high work function for easy hole injection.

The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, but embodiments are not limited thereto. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 110, at least one of magnesium (Mg), silver (Ag), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof may be used, but embodiments are not limited thereto.

The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers.

Emission Layer 15

The emission layer 15 may include the heterocyclic compound.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within the range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

First Embodiment—Descriptions of FIG. 4A

In the First Embodiment, the heterocyclic compound may be a fluorescence emitter. According to the First Embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host A’, and Host A may not be identical to the heterocyclic compound). Host A may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto. Host A may be a fluorescent host.

General energy transfer of the First Embodiment may be explained with reference to FIG. 4A.

Singlet excitons may be produced from Host A in the emission layer, and singlet excitons produced from Host A may be transferred to a fluorescence emitter through Förster energy transfer (FRET).

A ratio of singlet excitons produced from Host A may be 25%, and thus, 75% of triplet excitons produced from Host A may be fused to one another to be converted into singlet excitons. Thus, efficiency of the organic light-emitting device may be further improved. That is, efficiency of an organic light-emitting device may be further improved by using a triplet-triplet fusion mechanism.

According to the First Embodiment, a ratio of emission components emitted from the heterocyclic compound to the total emission components emitted from the emission layer may be 80% or greater, for example, 90% or greater. In an embodiment, a ratio of emission components emitted from the heterocyclic compound may be 95% or greater to the total emission components emitted from the emission layer.

The heterocyclic compound may emit fluorescence, and the host may not emit light.

In the First Embodiment, when the emission layer further includes Host A, in addition to the heterocyclic compound, an amount of the heterocyclic compound may be 50 parts by weight or less, e.g., 30 parts by weight or less, based on 100 parts by weight of the emission layer, and an amount of Host A in the emission layer may be 50 parts by weight or greater, e.g., 70 parts by weight or greater, based on 100 parts by weight of the emission layer, but embodiments are not limited thereto.

In the First Embodiment, when the emission layer further includes Host A, in addition to the heterocyclic compound, Host A and the heterocyclic compound may satisfy Condition A:

E(H_A)_S1>E_S1 Condition A

wherein, in Condition A,

E(H_A)_S1indicates a lowest excited singlet energy level of Host A, and

E_S1indicates a lowest excited singlet energy level of the heterocyclic compound.

Here, E(H_A)_S1and E_S1may be evaluated by using Gaussian according to density functional theory (DFT) method (wherein structure optimization is performed at a degree of B3LYP, and 6-31 G(d,p)).

Second Embodiment—Descriptions of FIG. 4B

In the Second Embodiment, the heterocyclic compound may be a delayed fluorescence emitter. According to the Second Embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host B’, and Host B may not be identical to the heterocyclic compound). Host B may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto.

General energy transfer of the Second Embodiment may be explained with reference to FIG. 4B.

25% of singlet excitons produced from Host B in the emission layer may be transferred to a delayed fluorescence emitter through FRET. In addition, 75% of triplet excitons produced from Host B in the emission layer may be transferred to a delayed fluorescence emitter through Dexter energy transfer. Energy transferred to a triplet state of a delayed fluorescence emitter may undergo RISC to a singlet state. Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the heterocyclic compound, an organic light-emitting device having improved efficiency may be obtained.

According to the Second Embodiment, a ratio of emission components emitted from the heterocyclic compound to the total emission components emitted from the emission layer may be 80% or greater, for example, 90% or greater. In an embodiment, a ratio of emission components emitted from the heterocyclic compound may be 95% or greater to the total emission components emitted from the emission layer.

Here, the heterocyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the heterocyclic compound may be a total of prompt emission components of the heterocyclic compound and delayed fluorescence components by RISC of the heterocyclic compound. In addition, Host B may not emit light.

In the Second Embodiment, when the emission layer further includes Host B, in addition to the heterocyclic compound, an amount of the heterocyclic compound may be 50 parts by weight or less, e.g., 30 parts by weight or less, based on 100 parts by weight of the emission layer, and an amount of Host B in the emission layer may be 50 parts by weight or greater, e.g., 70 parts by weight or greater, based on 100 parts by weight of the emission layer, but embodiments are not limited thereto.

In the Second Embodiment, when the emission layer further includes Host B, in addition to the heterocyclic compound, Host B and the heterocyclic compound may satisfy Condition B:

E(H_B)_S1>E_S1 Condition B

wherein, in Condition B,

E(H_B)_S1indicates a lowest excited singlet energy level of Host B, and E_S1indicates a lowest excited singlet energy level of the heterocyclic compound.

Here, E(H_B)_S1and E_S1may be evaluated by using Gaussian according to density functional theory (DFT) method (wherein structure optimization is performed at a degree of B3LYP, and 6-31 G(d,p)).

Third Embodiment and Fourth Embodiment
Third Embodiment—Description of FIG. 4C

In the Third Embodiment, the heterocyclic compound may be used as a fluorescence emitter, and the emission layer may include a sensitizer, e.g., a delayed fluorescence sensitizer. In the Third Embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as ‘Host C’, and Host C may not be identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as ‘Sensitizer A’, and Sensitizer A may not be identical to Host C and the heterocyclic compound). Host C and Sensitizer A may respectively be understood by referring to the description of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.

In the Third Embodiment, a ratio of emission components of the heterocyclic compound may be about 80% or greater, for example, 90% or greater (or for example, 95% or greater) to the total emission components emitted from the emission layer. For example, the heterocyclic compound may emit fluorescence. In addition, Host C and Sensitizer A may not each emit light.

General energy transfer of the Third Embodiment may be explained with reference to FIG. 4C.

Singlet and triplet excitons may be produced from Host C in the emission layer, and singlet and triplet excitons produced from Host C may be transferred to Sensitizer A and then to the heterocyclic compound through FRET. 25% of singlet excitons produced from Host C may be transferred to Sensitizer A through FRET, and energy of 75% of triplet excitons produced from Host C may be transferred to singlet and triplet states of Sensitizer A. Energy transferred to a triplet state of Sensitizer A may undergo RISC to a singlet state, and then, singlet energy of Sensitizer A may be transferred to the heterocyclic compound through FRET.

Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant, an organic light-emitting device having improved efficiency may be obtained. In addition, since an organic light-emitting device may be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device may be improved.

In the Third Embodiment, when the emission layer further includes Host C and Sensitizer A, in addition to the heterocyclic compound, Host C and Sensitizer A may satisfy Condition C-1 and/or C-2:

S₁(H_C)≥S₁(S_A) Condition C-1

S₁(S_A)≥S₁(HC) Condition C-2

wherein, in Conditions C-1 and C-2,

S₁(H_C) indicates a lowest excited singlet energy level of Host C,

S₁(S_A) indicates a lowest excited singlet energy level of Sensitizer A, and

S₁(HC) indicates a lowest excited singlet energy level of the heterocyclic compound.

S₁(H_C), S₁(S_A), and S₁(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, according to Gaussian according to DFT method.

When Host C, Sensitizer A, and the heterocyclic compound satisfy Condition C-1 and/or C-2, FRET from Sensitizer A to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.

Fourth Embodiment—Description of FIG. 4D

In the Fourth Embodiment, the heterocyclic compound may be used as a fluorescence emitter, and the emission layer may include a sensitizer, e.g., a phosphorescence sensitizer. In the Fourth Embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as ‘Host D’, and Host D may not be identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as ‘Sensitizer B’, and Sensitizer B may not be identical to Host D and the heterocyclic compound). Host D and Sensitizer B may respectively be understood by referring to the description of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.

In the Fourth Embodiment, a ratio of emission components of the heterocyclic compound may be about 80% or greater, for example, about 90% or greater (or for example, about 95% or greater) to the total emission components emitted from the emission layer. For example, the heterocyclic compound may emit fluorescence. In addition, Host D and Sensitizer B may not each emit light.

The general energy transfer of the Fourth Embodiment may be explained with reference to FIG. 4D.

75% of triplet excitons produced from Host D in the emission layer may be transferred to Sensitizer B through Dexter energy transfer, and energy of 25% of singlet excitons produced from Host D may be transferred to singlet and triplet states of Sensitizer B. Energy transferred to a singlet state of Sensitizer B may undergo ISC to a triplet state, and then, triplet energy of Sensitizer B may be transferred to the heterocyclic compound through FRET.

Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant, an organic light-emitting device having improved efficiency may be obtained. In addition, since an organic light-emitting device may be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device may be improved.

In the Fourth Embodiment, when the emission layer further includes Host D and Sensitizer B, in addition to the heterocyclic compound, Host D and Sensitizer B may satisfy Condition D-1 and/or D-2:

T₁(H_D)≥T₁(S_B) Condition D-1

T₁(S_B)≥S₁(HC) Condition D-2

wherein, in Conditions D-1 and D-2,

T₁(H_D) indicates a lowest excited triplet energy level of Host D,

T₁(S_B) indicates a lowest excited triplet energy level of Sensitizer B, and

S₁(HC) indicates a lowest excited singlet energy level of the heterocyclic compound.

T₁(H_D), T₁(S_B), and S₁(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, according to Gaussian according to DFT method.

When Host D, Sensitizer B, and the heterocyclic compound satisfy Condition D-1 and/or D-2, FRET from Sensitizer B to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.

In the Third Embodiment and the Fourth Embodiment, an amount of the sensitizer in the emission layer may be in a range of about 5 percent by weight (wt %) to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the amount is within this range, energy transfer in the emission layer may be effectively occurred. Thus, the organic light-emitting device may have high efficiency and long lifespan.

In the Third Embodiment and the Fourth Embodiment, an amount of the heterocyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.

In the Third Embodiment and the Fourth Embodiment, the sensitizer and the heterocyclic compound may satisfy Condition 5:

0 μs<T_decay(HC)<5 μs Condition 5

wherein, in Condition 5,

T_decay(HC) is a decay time of the heterocyclic compound.

The decay time of the heterocyclic compound was measured from a time-resolved photoluminescence (TRPL) spectrum at room temperature of a film (hereinafter, referred to as “Film (HC)”) having a thickness of 40 nm formed by vacuum-depositing the host and the heterocyclic compound included in the emission layer on a quartz substrate at a weight ratio of 90:10 at a vacuum pressure of 10-7 torr.

Fifth Embodiment—Description of FIG. 4E

In the Fifth Embodiment, the heterocyclic compound may be used as a delayed fluorescence emitter, and the emission layer may include a sensitizer, e.g., a delayed fluorescence sensitizer. In the Fifth Embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as ‘Host E’, and Host E may not be identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as ‘Sensitizer C’, and Sensitizer C may not be identical to Host E and the heterocyclic compound). Host E and Sensitizer C may respectively be understood by referring to the description of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.

In the Fifth Embodiment, a ratio of emission components of the heterocyclic compound may be about 80% or greater, for example, about 90% or greater (or for example, about 95% or greater) to the total emission components emitted from the emission layer. In an embodiment, the heterocyclic compound may emit fluorescence and/or delayed fluorescence. In addition, Host E and Sensitizer C may not each emit light.

Here, the heterocyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the heterocyclic compound may be a total of prompt emission components of the heterocyclic compound and delayed fluorescence components by RISC of the heterocyclic compound.

The general energy transfer of the Fifth Embodiment may be explained with reference to FIG. 4E.

25% of singlet excitons produced from Host E in the emission layer may be transferred to a singlet state of Sensitizer C through FRET, and energy of 75% of triplet excitons produced from Host E may be transferred to a triplet state of Sensitizer C, and then singlet energy of Sensitizer C may be transferred to the heterocyclic compound through FRET. Subsequently, the triplet energy of Sensitizer C may be transferred to the heterocyclic compound through Dexter energy transfer. Energy transferred to a triplet state of Sensitizer C may undergo RISC to a singlet state. Further, in a case of Sensitizer C, energy of triplet excitons produced from Sensitizer C may undergo reverse transfer to Host E and then to the heterocyclic compound, thus emitting by reverse intersystem transfer.

Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant, an organic light-emitting device having improved efficiency may be obtained. In addition, since an organic light-emitting device may be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device may be improved.

In the Fifth Embodiment, when the emission layer further includes Host E and Sensitizer C, in addition to the heterocyclic compound, Host E and Sensitizer C may satisfy Condition E-1, E-2, and/or E-3:

S₁(H_E)≥S₁(S_C) Condition E-1

S₁(S_C)≥S₁(HC) Condition E-2

T₁(S_C)≥T₁(HC) Condition E-3

wherein, in Conditions E-1, E-2, and E-3,

S₁(H_E) indicates a lowest excited singlet energy level of Host E,

S₁(S_C) indicates a lowest excited singlet energy level of Sensitizer C,

S₁(HC) indicates a lowest excited singlet energy level of the heterocyclic compound,

T₁(S_C) indicates a lowest excited triplet energy level of Sensitizer C, and

T₁(HC) indicates a lowest excited triplet energy level of the heterocyclic compound.

S₁(H_E), S₁(S_C), S₁(HC), T₁(S_C), and T₁(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31 G(d,p), for example, according to Gaussian according to DFT method.

When Host E, Sensitizer C, and the heterocyclic compound satisfy Condition E-1, E-2, and/or E-3, Dexter transfer FRET from Sensitizer C to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.

In the Fifth Embodiment, an amount of Sensitizer C in the emission layer may be in a range of about 5 wt % to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the amount is within this range, energy transfer in the emission layer may be effectively occurred. Thus, the organic light-emitting device may have high efficiency and long lifespan.

In the Fifth Embodiment, an amount of the heterocyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.

Host in Emission Layer 15

The host may not include a metal atom.

In an embodiment, the host may include one kind of host. When the host includes one host, the one host may be a bipolar host, an electron-transporting host, or a hole-transporting host, which will be described later.

In an embodiment, the host may include a mixture of two or more different hosts. For example, the host may be a mixture of an electron-transporting host and a hole-transporting host, a mixture of two types of electron-transporting hosts different from each other, or a mixture of two types of hole-transporting hosts different from each other. The electron-transporting host and the hole-transporting host may be understood by referring to the related description to be presented later.

In an embodiment, the host may include an electron-transporting host including at least one electron-transporting moiety and a hole-transporting host that is free of an electron-transporting moiety.

The electron-transporting moiety used herein may be a cyano group, a π electron-deficient nitrogen-containing cyclic group, and a group represented by one of the following Formulae:

[Image Omitted]

wherein, in Formulae ET-moiety, *, *′, and *″ may each indicate a binding site to an adjacent atom.

In an embodiment, the electron-transporting host of the emission layer 15 may include at least one of a cyano group, a π electron-deficient nitrogen-containing cyclic group, or a combination thereof.

In an embodiment, the electron-transporting host in the emission layer 15 may include at least one cyano group.

In an embodiment, the electron-transporting host in the emission layer 15 may include at least one cyano group, at least one π electron-deficient nitrogen-containing cyclic group, or a combination thereof.

In an embodiment, the host may include an electron-transporting host and a hole-transporting host, wherein the electron-transporting host may include at least one π electron-deficient nitrogen-free cyclic group, at least one electron-transporting moiety, or a combination thereof, and the hole-transporting host may include at least one π electron-deficient nitrogen-free cyclic group and may not include an electron-transporting moiety.

The term “π electron-deficient nitrogen-containing cyclic group” used herein refers to a cyclic group having at least one *—N═*′ moiety, and for example, may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; or a condensed cyclic group in which two or more π electron-efficient nitrogen-containing cyclic groups are condensed with each other.

Meanwhile, the π electron-deficient nitrogen-free cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group, or a condensed cyclic group of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the disclosure are not limited thereto.

In an embodiment, the electron-transporting host may be a compound represented by Formula E-1, and

the hole-transporting host may be a compound represented by Formula H-1, but embodiments of the disclosure are not limited thereto:

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21 Formula E-1

wherein, in Formula E-1,

Ar₃₀₁may be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁may each independently be a single bond, a group represented by one of following Formulae, a substituted or unsubstituted C₅-C₆₀carbocyclic group, or a substituted or unsubstituted C₁-C₆₀heterocyclic group, wherein in the following Formulae, *, *′, and *″ may each indicate a binding site to an adjacent atom,

[Image Omitted]

xb1 may be an integer from 1 to 5,

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), —S(═O)(Q₃₀₁), —P(═O)(Q₃₀₁)(Q₃₀₂), or —P(═S)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5,

wherein Q₃₀₁to Q₃₀₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and

at least one of Condition H-1 to Condition H-3 is satisfied:

Condition H-1

at least one of Ar₃₀₁, L₃₀₁, and R₃₀₁in Formula E-1 may each independently include a π electron-depleted nitrogen-containing cyclic group,

Condition H-2

in Formula E-1, L₃₀₁may be a group represented by one of the following Formulae, and

[Image Omitted]

Condition H-3

in Formula E-1, R₃₀₁may be a cyano group, —S(═O)₂(Q₃₀₁), —S(═O)(Q₃₀₁), —P(═O)(Q₃₀₁)(Q₃₀₂), or —P(═S)(Q₃₀₁)(Q₃₀₂).

[Image Omitted]

wherein, in Formulae H-1, 11, and 12,

L₄₀₁may be:

a single bond; or

a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group, each unsubstituted or substituted with at least one deuterium, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), or a combination thereof,

xd1 may be an integer from 1 to 10; and when xd1 is 2 or greater, at least two L₄₀₁groups may be identical to or different from each other,

Ar₄₀₁may be a group represented by Formulae 11 or 12,

Ar₄₀₂may be:

a group represented by Formula 11 or 12, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group; or

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, each substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, or a combination thereof,

CY₄₀₁and CY₄₀₂may each independently be a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonapthothiophene group, or a benzonaphthosilole group,

A₂₁may be a single bond, O, S, N(R₅₁), C(R₅₁)(R₅₂), or Si(R₅₁)(R₅₂),

A₂₂may be a single bond, O, S, N(R₅₃), C(R₅₃)(R₅₄), or Si(R₅₃)(R₅₄),

at least one of A₂₁and A₂₂in Formula 12 may not be a single bond,

R₅₁to R₅₄, R₆₀, and R₇₀may each independently be:

hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, or a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group or a C₁-C₂₀alkoxy group, each substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof;

a π electron-depleted nitrogen-free cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group);

a π electron-depleted nitrogen-free cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group) substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, or a combination thereof,

—Si(Q₄₀₄)(Q₄₀₅)(Q₄₀₆),

e1 and e2 may each independently be an integer from 0 to 10,

Q₄₀₁to Q₄₀₆may each independently be hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, or a combination thereof, and

* indicates a binding site to a neighboring atom.

In an embodiment, in Formula E-1, Ar₃₀₁and L₃₀₁may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or a combination thereof,

at least one of L₃₀₁(s) in the number of xb1 may each independently be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or a combination thereof, and

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing tetraphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but embodiments are not limited thereto.

In an embodiment, Ar₃₀₁may be

a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or a combination thereof; or

a group represented by one of Formulae 5-1 to 5-3 and 6-1 to 6-33, and

L₃₀₁may be a group represented by one of Formulae 5-1 to 5-3 and 6-1 to 6-33:

[Image Omitted]

wherein, in Formulae 5-1 to 5-3 and 6-1 to 6-33,

Z₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

d4 may be 0, 1, 2, 3, or 4,

d3 may be 0, 1, 2, or 3,

d2 may be 0, 1, or 2, and

* and *′ each indicate a binding site to an adjacent atom.

Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₃₁to Q₃₃provided herein.

In an embodiment, L₃₀₁may be a group represented by one of Formulae 5-2, 5-3 and 6-8 to 6-33.

In an embodiment, R₃₀₁may be a cyano group or a group represented by one of Formulae 7-1 to 7-18, and at least one of Ar₄₀₂(s) in the number of xd11 may be a group represented by one of Formulae 7-1 to 7-18, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

wherein, in Formulae 7-1 to 7-18

xb41 to xb44 may each be 0, 1, or 2, provided that xb41 in Formula 7-10 may not be 0, xb41+xb42 in Formulae 7-11 to 7-13 may not be 0, xb41+xb42+xb43 in Formulae 7-14 to 7-16 may not be 0, xb41+xb42+xb43+xb44 in Formulae 7-17 and 7-18 may not be 0, and * indicates a binding site to an adjacent atom.

In Formula E-1, at least two Ar₃₀₁(s) may be identical to or different from each other, and at least two L₃₀₁(s) may be identical to or different from each other. In Formula H-1, at least two L₄₀₁(s) may be identical to or different from each other, and at least two Ar₄₀₂(s) may be identical to or different from each other.

In an embodiment, the electron-transporting host includes i) at least one of a cyano group, a pyrimidine group, a pyrazine group, a triazine group, or a combination thereof, or ii) a triphenylene group, and the hole-transporting host may include a carbazole group.

In an embodiment, the electron-transporting host may include at least one cyano group.

The electron-transporting host may be, for example, a compound of Groups HE1 to HE7, but embodiments are not limited thereto:

[Image Omitted]

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In an embodiment, the electron-transporting host may include DPEPO and TSPO1:

[Image Omitted]

In an embodiment, the hole-transporting host may be of Group HH1, but embodiments are not limited thereto:

[Image Omitted]

In an embodiment, the bipolar host may be of Group HEH1, but embodiments are not limited thereto:

[Image Omitted]

[Image Omitted]

[Image Omitted]

wherein in Compounds 1 to 432,

“Ph” represents a phenyl group.

In an embodiment, the hole-transporting host may include o-CBP or mCP:

[Image Omitted]

In an embodiment, the host may be a fluorescent host, and the fluorescent host may be represented by, for example, one of Formulae FH-1 to FH-4.

In an embodiment, the fluorescent host may be represented by Formula FH-1 below:

[Image Omitted]

wherein, in Formula FH-1,

Ar₁to Ar₃may each independently be a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

at least one of Ar₁to Ar₃may be a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

L₁₀may be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a10 may be an integer from 0 to 3, and when a10 is 2 or more, two or more of L₁₀(s) may be identical to or different from each other,

R₁₀and R₂₀may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b10 and b20 may each independently an integer from 1 to 8,

when b10 is 2 or more, two or more of R₁₀(s) may be identical to or different from each other, and when b20 is 2 or more, two or more of R₂₀(s) may be identical to or different from each other,

c10 may be an integer from 1 to 9,

when c10 is 2 or more, two or more of -[(L₁₀)_a10-(R₁₀)_b10] may be identical to or different from each other, and Q₁to Q₉may be the same as defined hereinafter.

In an embodiment, a fluorescent host represented by Formula FH-1 may be Group FH1 below, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

In an embodiment, the fluorescent host may be represented by Formula FH-2 below:

[Image Omitted]

wherein, in Formula FH-2,

X₁may be O or S,

A₁may be a C₅-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

L₁₁may be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

a11 may be an integer from 0 to 3,

Ar₁₁and Ar₁₂may each independently be a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one R_a,

b11 is an integer from 1 to 5,

R₁₁, R₁₂, and R_amay each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), or —B(Q₆)(Q₇),

c11 may be an integer from 1 to 20,

c12 may be an integer from 1 to 4,

when c11 is 2 or more, two neighboring R₁₁may optionally be bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group, and a substituted or unsubstituted C₁-C₃₀heterocyclic group,

when c12 is 2 or more, two neighboring R₁₂may optionally be bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group and a substituted or unsubstituted C₁-C₃₀heterocyclic group,

A₁and Ar₁₂may optionally be bonded together via a first linking group a single bond, *—Ar₃₁—*′, *—O—*′, *—S—*′, *—[C(R₃₁)(R₃₂)]_k11—*′, *—C(R₃₁)═*′, *═C(R₃₁)—*′, *—C(R₃₁)═C(R₃₂)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—N(R₃₁)—*′, *—P(R₃₁)—*′, *—[Si(R₃₁)(R₃₂)]_k11—*′, and *—P(R₃₁)(R₃₂)—*′ to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

Ar₃₁may be a C₅-C₃₀carbocyclic group,

R₃₁and R₃₂are respectively the same as described in connection with R₁₁,

k11 may be 1, 2, 3, or 4, and Q₁to Q₇may be the same as defined hereinafter.

In an embodiment, a fluorescent host represented by Formula FH-2 may be of Group FH2 below, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

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In an embodiment, the fluorescent host may be represented by Formula FH-3 below:

[Image Omitted]

wherein, in Formula FH-3,

Ar₁may be a group represented by Formula 2 below,

[Image Omitted]

Ar₁may include at least one cyano group,

A₁and A₂may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group,

L₁may be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a1 may be 0, 1, 2, or 3,

when a1 is 2 or more, two or more of Li(s) may be identical to or different from each other,

m1 may be 0, 1, 2, or 3,

Ar₁₁may be a group represented by Formula 4 below, Ar₁₂may be a group represented by Formula 5 below, and Ar₁₃may be a group represented by Formula 6 below,

[Image Omitted]

wherein, in Formulae above,

R₁, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b1 may be an integer from 1 to 5,

when b1 is 2 or more, two or more of R₁(s) may be identical to or different from each other,

b10 may be an integer from 1 to 8,

when b10 is 2 or more, two or more of R₁₀(s) may be identical to or different from each other,

b20 and b30 may each independently be an integer from 1 to 4,

when b20 is 2 or more, two or more of R₂₀(s) may be identical to or different from each other, and when b30 is 2 or more, two or more of R₃₀(s) may be identical to or different from each other,

b40, b50, and b60 may each independently be an integer from 1 to 4,

when b40 is 2 or more, two or more of R₄₀(s) may be identical to or different from each other, when b50 is 2 or more, two or more of R₅₀(s) may be identical to or different from each other, and when b60 is 2 or more, two or more of R₆₀(s) may be identical to or different from each other,

* and *′ each indicate a binding site to a neighboring atom, and Q₁to Q₉may be the same as defined hereinafter.

In an embodiment, a fluorescent host represented by Formula FH-3 may be one of Group FH3 below, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

In an embodiment, the fluorescent host may be represented by one of Formula FH-4 below:

[Image Omitted]

wherein, in Formula FH-4,

X₁may be O or Se,

Ar₁may be a group represented by Formula 1A below, or Ar₂may be a group represented by Formula 1B below,

[Image Omitted]

wherein, in Formulae above,

L₁and L₂may each independently a substituted or unsubstituted C₅-C₃₀carbocyclic group, or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a1 and a2 may each independently be an integer from 0 to 3,

wherein when a1 is 2 or more, two or more of L₁(s) may be identical to or different from each other, and when a2 is 2 or more, two or more of L₂(s) may be identical to or different from each other,

R₁, R₂, R₁₀, R₂₀, R₃₀, and R₄₀may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b1 and b2 may each independently be an integer from 1 to 5,

wherein when b1 is 2 or more, two or more of R₁(s) may be identical to or different from each other, and when b2 is 2 or more, two or more of R₂(s) may be identical to or different from each other,

b10 and b20 may each independently an integer from 1 to 8,

b30 and b40 may each independently an integer from 1 to 3,

c1 and c2 may each independently be an integer from 1 to 8,

the sum of b10 and c1 may be 9, and the sum of b20 and c2 may be 9, and Q₁to Q₉may be the same as defined hereinafter.

In an embodiment, a fluorescent host represented by Formula FH-4 may be one of Group FH4 below, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

When the host is a mixture of an electron-transporting host and a hole-transporting host, the weight ratio of the electron-transporting host and the hole-transporting host may be about 1:9 to 9:1, for example, about 2:8 to 8:2, for example, about 4:6 to 6:4, for example, about 5:5. When the weight ratio of the electron-transporting host and the hole-transporting host satisfies the above-described ranges, the hole-and-electron-transporting balance in the emission layer 15 may be made.

Dopant in Emission Layer 15

The dopant includes the heterocyclic compound.

Sensitizer in Emission Layer 15

In an embodiment, the sensitizer may be a phosphorescent sensitizer including at least one metal of a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, a third-row transition metal of the Periodic Table of Elements, or a combination thereof.

In an embodiment, the sensitizer may include at least one metal (M₁₁) of a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, a third-row transition metal of the Periodic Table of Elements, or a combination thereof, and an organic ligand (L₁), and L₁₁and M₁₁may form 1, 2, 3, or 4 cyclometallated rings.

In an embodiment, the sensitizer may include an organometallic compound represented by Formula 101:

M₁₁(L₁₁)_n11(L₁₂)_n12 Formula 101

wherein, in Formula 101,

M₁₁may be a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, a third-row transition metal of the Periodic Table of Elements, or a combination thereof;

L₁₁is a ligand represented by one of Formulae 1-1 to 1-4;

L₁₂is a monodentate ligand or a bidentate ligand;

n11 is 1,

n12 is 0, 1, or 2;

[Image Omitted]

wherein, in Formulae 1-1 to 1-4,

A₁to A₄may each independently be a substituted or unsubstituted C₅-C₃₀carbocyclic group, a substituted or unsubstituted C₁-C₃₀heterocyclic group, or a non-cyclic group,

Y₁₁to Y₁₄may each independently be a chemical bond, O, S, N(R₉₁), B(R₉₁), P(R₉₁), or C(R₉₁)(R₉₂),

T₁to T₄may each independently be a single bond, a double bond, *—N(R₉₃)—*′, *—B(R₉₃)—*′, *—P(R₉₃)—*′, *—C(R₉₃)(R₉₄)—*′, *—Si(R₉₃)(R₉₄)—*′, *—Ge(R₉₃)(R₉₄)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₉₃)═*′, *═C(R₉₃)—*′, *—C(R₉₃)═C(R₉₄)—*′, *—C(═S)—*′, or *—C≡C—*′,

a substituent of the substituted C₅-C₃₀carbocyclic group, a substituent of the substituted C₁-C₃₀heterocyclic group, and R₉₁to R₉₄may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), or —P(═S)(Q₁)(Q₂), wherein the substituent of the substituted C₅-C₃₀carbocyclic group and the substituent of the substituted C₁-C₃₀heterocyclic group are not hydrogen,

*₁, *₂, *₃, and *₄each indicate a binding site to M₁₁, and

Q₁to Q₃may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof, or a C₆-C₆₀aryl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof.

In an embodiment, the sensitizer may be Groups I to VIII, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

Group V

a compound represented by Formula A below:

(L₁₀₁)_n101-M₁₀₁-(L₁₀₂)_m101 Formula A

wherein, in Formula A, L₁₀₁, n101, M₁₀₁, L₁₀₂, and m101 are respectively the same as shown in Tables 11 to 13 below:

TABLE 2

Compound

name
L₁₀₁
n101
M₁₀₁
L₁₀₂
m101

BD001
LM1
3
Ir
—
0

BD002
LM2
3
Ir
—
0

BD003
LM3
3
Ir
—
0

BD004
LM4
3
Ir
—
0

BD005
LM5
3
Ir
—
0

BD006
LM6
3
Ir
—
0

BD007
LM7
3
Ir
—
0

BD008
LM8
3
Ir
—
0

BD009
LM9
3
Ir
—
0

BD010
LM10
3
Ir
—
0

BD011
LM11
3
Ir
—
0

BD012
LM12
3
Ir
—
0

BD013
LM13
3
Ir
—
0

BD014
LM14
3
Ir
—
0

BD015
LM15
3
Ir
—
0

BD016
LM16
3
Ir
—
0

BD017
LM17
3
Ir
—
0

BD018
LM18
3
Ir
—
0

BD019
LM19
3
Ir
—
0

BD020
LM20
3
Ir
—
0

BD021
LM21
3
Ir
—
0

BD022
LM22
3
Ir
—
0

BD023
LM23
3
Ir
—
0

BD024
LM24
3
Ir
—
0

BD025
LM25
3
Ir
—
0

BD026
LM26
3
Ir
—
0

BD027
LM27
3
Ir
—
0

BD028
LM28
3
Ir
—
0

BD029
LM29
3
Ir
—
0

BD030
LM30
3
Ir
—
0

BD031
LM31
3
Ir
—
0

BD032
LM32
3
Ir
—
0

BD033
LM33
3
Ir
—
0

BD034
LM34
3
Ir
—
0

BD035
LM35
3
Ir
—
0

BD036
LM36
3
Ir
—
0

BD037
LM37
3
Ir
—
0

BD038
LM38
3
Ir
—
0

BD039
LM39
3
Ir
—
0

BD040
LM40
3
Ir
—
0

BD041
LM41
3
Ir
—
0

BD042
LM42
3
Ir
—
0

BD043
LM43
3
Ir
—
0

BD044
LM44
3
Ir
—
0

BD045
LM45
3
Ir
—
0

BD046
LM46
3
Ir
—
0

BD047
LM47
3
Ir
—
0

BD048
LM48
3
Ir
—
0

BD049
LM49
3
Ir
—
0

BD050
LM50
3
Ir
—
0

BD051
LM51
3
Ir
—
0

BD052
LM52
3
Ir
—
0

BD053
LM53
3
Ir
—
0

BD054
LM54
3
Ir
—
0

BD055
LM55
3
Ir
—
0

BD056
LM56
3
Ir
—
0

BD057
LM57
3
Ir
—
0

BD058
LM58
3
Ir
—
0

BD059
LM59
3
Ir
—
0

BD060
LM60
3
Ir
—
0

BD061
LM61
3
Ir
—
0

BD062
LM62
3
Ir
—
0

BD063
LM63
3
Ir
—
0

BD064
LM64
3
Ir
—
0

BD065
LM65
3
Ir
—
0

BD066
LM66
3
Ir
—
0

BD067
LM67
3
Ir
—
0

BD068
LM68
3
Ir
—
0

BD069
LM69
3
Ir
—
0

BD070
LM70
3
Ir
—
0

BD071
LM71
3
Ir
—
0

BD072
LM72
3
Ir
—
0

BD073
LM73
3
Ir
—
0

BD074
LM74
3
Ir
—
0

BD075
LM75
3
Ir
—
0

BD076
LM76
3
Ir
—
0

BD077
LM77
3
Ir
—
0

BD078
LM78
3
Ir
—
0

BD079
LM79
3
Ir
—
0

BD080
LM80
3
Ir
—
0

BD081
LM81
3
Ir
—
0

BD082
LM82
3
Ir
—
0

BD083
LM83
3
Ir
—
0

BD084
LM84
3
Ir
—
0

BD085
LM85
3
Ir
—
0

BD086
LM86
3
Ir
—
0

BD087
LM87
3
Ir
—
0

BD088
LM88
3
Ir
—
0

BD089
LM89
3
Ir
—
0

BD090
LM90
3
Ir
—
0

BD091
LM91
3
Ir
—
0

BD092
LM92
3
Ir
—
0

BD093
LM93
3
Ir
—
0

BD094
LM94
3
Ir
—
0

BD095
LM95
3
Ir
—
0

BD096
LM96
3
Ir
—
0

BD097
LM97
3
Ir
—
0

BD098
LM98
3
Ir
—
0

BD099
LM99
3
Ir
—
0

BD100
LM100
3
Ir
—
0

TABLE 3

Compound

name
L₁₀₁
n101
M₁₀₁
L₁₀₂
m101

BD101
LM101
3
Ir
—
0

BD102
LM102
3
Ir
—
0

BD103
LM103
3
Ir
—
0

BD104
LM104
3
Ir
—
0

BD105
LM105
3
Ir
—
0

BD106
LM106
3
Ir
—
0

BD107
LM107
3
Ir
—
0

BD108
LM108
3
Ir
—
0

BD109
LM109
3
Ir
—
0

BD110
LM110
3
Ir
—
0

BD111
LM111
3
Ir
—
0

BD112
LM112
3
Ir
—
0

BD113
LM113
3
Ir
—
0

BD114
LM114
3
Ir
—
0

BD115
LM115
3
Ir
—
0

BD116
LM116
3
Ir
—
0

BD117
LM117
3
Ir
—
0

BD118
LM118
3
Ir
—
0

BD119
LM119
3
Ir
—
0

BD120
LM120
3
Ir
—
0

BD121
LM121
3
Ir
—
0

BD122
LM122
3
Ir
—
0

BD123
LM123
3
Ir
—
0

BD124
LM124
3
Ir
—
0

BD125
LM125
3
Ir
—
0

BD126
LM126
3
Ir
—
0

BD127
LM127
3
Ir
—
0

BD128
LM128
3
Ir
—
0

BD129
LM129
3
Ir
—
0

BD130
LM130
3
Ir
—
0

BD131
LM131
3
Ir
—
0

BD132
LM132
3
Ir
—
0

BD133
LM133
3
Ir
—
0

BD134
LM134
3
Ir
—
0

BD135
LM135
3
Ir
—
0

BD136
LM136
3
Ir
—
0

BD137
LM137
3
Ir
—
0

BD138
LM138
3
Ir
—
0

BD139
LM139
3
Ir
—
0

BD140
LM140
3
Ir
—
0

BD141
LM141
3
Ir
—
0

BD142
LM142
3
Ir
—
0

BD143
LM143
3
Ir
—
0

BD144
LM144
3
Ir
—
0

BD145
LM145
3
Ir
—
0

BD146
LM146
3
Ir
—
0

BD147
LM147
3
Ir
—
0

BD148
LM148
3
Ir
—
0

BD149
LM149
3
Ir
—
0

BD150
LM150
3
Ir
—
0

BD151
LM151
3
Ir
—
0

BD152
LM152
3
Ir
—
0

BD153
LM153
3
Ir
—
0

BD154
LM154
3
Ir
—
0

BD155
LM155
3
Ir
—
0

BD156
LM156
3
Ir
—
0

BD157
LM157
3
Ir
—
0

BD158
LM158
3
Ir
—
0

BD159
LM159
3
Ir
—
0

BD160
LM160
3
Ir
—
0

BD161
LM161
3
Ir
—
0

BD162
LM162
3
Ir
—
0

BD163
LM163
3
Ir
—
0

BD164
LM164
3
Ir
—
0

BD165
LM165
3
Ir
—
0

BD166
LM166
3
Ir
—
0

BD167
LM167
3
Ir
—
0

BD168
LM168
3
Ir
—
0

BD169
LM169
3
Ir
—
0

BD170
LM170
3
Ir
—
0

BD171
LM171
3
Ir
—
0

BD172
LM172
3
Ir
—
0

BD173
LM173
3
Ir
—
0

BD174
LM174
3
Ir
—
0

BD175
LM175
3
Ir
—
0

BD176
LM176
3
Ir
—
0

BD177
LM177
3
Ir
—
0

BD178
LM178
3
Ir
—
0

BD179
LM179
3
Ir
—
0

BD180
LM180
3
Ir
—
0

BD181
LM181
3
Ir
—
0

BD182
LM182
3
Ir
—
0

BD183
LM183
3
Ir
—
0

BD184
LM184
3
Ir
—
0

BD185
LM185
3
Ir
—
0

BD186
LM186
3
Ir
—
0

BD187
LM187
3
Ir
—
0

BD188
LM188
3
Ir
—
0

BD189
LM189
3
Ir
—
0

BD190
LM190
3
Ir
—
0

BD191
LM191
3
Ir
—
0

BD192
LM192
3
Ir
—
0

BD193
LM193
3
Ir
—
0

BD194
LM194
3
Ir
—
0

BD195
LM195
3
Ir
—
0

BD196
LM196
3
Ir
—
0

BD197
LM197
3
Ir
—
0

BD198
LM198
3
Ir
—
0

BD199
LM199
3
Ir
—
0

BD200
LM200
3
Ir
—
0

TABLE 4

Compound

name
L₁₀₁
n101
M₁₀₁
L₁₀₂
m101

BD201
LM201
3
Ir
—
0

BD202
LM202
3
Ir
—
0

BD203
LM203
3
Ir
—
0

BD204
LM204
3
Ir
—
0

BD205
LM205
3
Ir
—
0

BD206
LM206
3
Ir
—
0

BD207
LM207
3
Ir
—
0

BD208
LM208
3
Ir
—
0

BD209
LM209
3
Ir
—
0

BD210
LM210
3
Ir
—
0

BD211
LM211
3
Ir
—
0

BD212
LM212
3
Ir
—
0

BD213
LM213
3
Ir
—
0

BD214
LM214
3
Ir
—
0

BD215
LM215
3
Ir
—
0

BD216
LM216
3
Ir
—
0

BD217
LM217
3
Ir
—
0

BD218
LM218
3
Ir
—
0

BD219
LM219
3
Ir
—
0

BD220
LM220
3
Ir
—
0

BD221
LM221
3
Ir
—
0

BD222
LM222
3
Ir
—
0

BD223
LM223
3
Ir
—
0

BD224
LM224
3
Ir
—
0

BD225
LM225
3
Ir
—
0

BD226
LM226
3
Ir
—
0

BD227
LM227
3
Ir
—
0

BD228
LM228
3
Ir
—
0

BD229
LM229
3
Ir
—
0

BD230
LM230
3
Ir
—
0

BD231
LM231
3
Ir
—
0

BD232
LM232
3
Ir
—
0

BD233
LM233
3
Ir
—
0

BD234
LM234
3
Ir
—
0

BD235
LM235
3
Ir
—
0

BD236
LM236
3
Ir
—
0

BD237
LM273
3
Ir
—
0

BD238
LM238
3
Ir
—
0

BD239
LM239
3
Ir
—
0

BD240
LM240
3
Ir
—
0

BD241
LM241
3
Ir
—
0

BD242
LM242
3
Ir
—
0

BD243
LM243
3
Ir
—
0

BD244
LFM1
3
Ir
—
0

BD245
LFM2
3
Ir
—
0

BD246
LFM3
3
Ir
—
0

BD247
LFM4
3
Ir
—
0

BD248
LFM5
3
Ir
—
0

BD249
LFM6
3
Ir
—
0

BD250
LFM7
3
Ir
—
0

BD251
LFP1
3
Ir
—
0

BD252
LFP2
3
Ir
—
0

BD253
LFP3
3
Ir
—
0

BD254
LFP4
3
Ir
—
0

BD255
LFP5
3
Ir
—
0

BD256
LFP6
3
Ir
—
0

BD257
LFP7
3
Ir
—
0

BD258
LM47
2
Ir
AN1
1

BD259
LM47
2
Ir
AN2
1

BD260
LM47
2
Ir
AN3
1

BD261
LM47
2
Ir
AN4
1

BD262
LM47
2
Ir
AN5
1

BD263
LM11
2
Pt
—
0

BD264
LM13
2
Pt
—
0

BD265
LM15
2
Pt
—
0

BD266
LM45
2
Pt
—
0

BD267
LM47
2
Pt
—
0

BD268
LM49
2
Pt
—
0

BD269
LM98
2
Pt
—
0

BD270
LM100
2
Pt
—
0

BD271
LM102
2
Pt
—
0

BD272
LM132
2
Pt
—
0

BD273
LM134
2
Pt
—
0

BD274
LM136
2
Pt
—
0

BD275
LM151
2
Pt
—
0

BD276
LM153
2
Pt
—
0

BD277
LM158
2
Pt
—
0

BD278
LM180
2
Pt
—
0

BD279
LM182
2
Pt
—
0

BD280
LM187
2
Pt
—
0

BD281
LM201
2
Pt
—
0

BD282
LM206
2
Pt
—
0

BD283
LM211
2
Pt
—
0

BD284
LM233
2
Pt
—
0

BD285
LM235
2
Pt
—
0

BD286
LM240
2
Pt
—
0

BD287
LFM5
2
Pt
—
0

BD288
LFM6
2
Pt
—
0

BD289
LFM7
2
Pt
—
0

BD290
LFP5
2
Pt
—
0

BD291
LFP6
2
Pt
—
0

BD292
LFP7
2
Pt
—
0

BD293
LM47
1
Pt
AN1
1

BD294
LM47
1
Pt
AN2
1

BD295
LM47
1
Pt
AN3
1

BD296
LM47
1
Pt
AN4
1

BD297
LM47
1
Pt
AN5
1

LM1 to LM243 in Tables 2 to 4 may be understood by referring to Formulae 1-1 to 1-3 and Tables 5 to 7:

[Image Omitted]

TABLE 5

Formula 1-1

Ligand name
R₁₁
R₁₂
R₁₃
R₁₄
R₁₅
R₁₆
R₁₇
R₁₈
R₁₉
R₂₀

LM1
X1
H
X3
H
X1
H
H
H
H
D

LM2
X1
H
X3
H
X1
H
H
H
D
H

LM3
X1
H
X3
H
X1
H
H
H
D
D

LM4
Y1
H
X3
H
Y1
H
H
H
D
D

LM5
Y2
H
X3
H
Y2
H
H
H
D
D

LM6
Y3
H
X3
H
Y3
H
H
H
D
D

LM7
Y3
D
X3
D
Y3
H
H
H
D
D

LM8
Y3
D
X3
D
Y3
D
H
H
D
D

LM9
Y3
D
X3
D
Y3
D
D
H
D
D

LM10
Y3
D
X3
D
Y3
D
D
D
D
D

LM11
Y3
D
Y11
D
Y3
D
D
D
D
D

LM12
Y3
D
Y11
D
Y3
H
X1
H
D
D

LM13
Y3
D
Y11
D
Y3
D
Y3
D
D
D

LM14
Y3
D
Y11
D
Y3
H
X4
H
D
D

LM15
Y3
D
Y11
D
Y3
D
Y12
D
D
D

LM16
X2
H
X3
H
X2
H
H
H
H
D

LM17
X2
H
X3
H
X2
H
H
H
D
H

LM18
X2
H
X3
H
X2
H
H
H
D
D

LM19
Y4
H
X3
H
Y4
H
H
H
D
D

LM20
Y5
H
X3
H
Y5
H
H
H
D
D

LM21
Y6
H
X3
H
Y6
H
H
H
D
D

LM22
Y7
H
X3
H
Y7
H
H
H
D
D

LM23
Y8
H
X3
H
Y8
H
H
H
D
D

LM24
Y9
H
X3
H
Y9
H
H
H
D
D

LM25
Y10
H
X3
H
Y10
H
H
H
D
D

LM26
Y10
D
X3
D
Y10
H
H
H
D
D

LM27
Y10
D
X3
D
Y10
D
H
H
D
D

LM28
Y10
D
X3
D
Y10
D
D
H
D
D

LM29
Y10
D
X3
D
Y10
D
D
D
D
D

LM30
Y10
D
Y11
D
Y10
D
D
D
D
D

LM31
Y10
D
Y11
D
Y10
H
X1
H
D
D

LM32
Y10
D
Y11
D
Y10
D
Y3
D
D
D

LM33
Y10
D
Y11
D
Y10
H
X4
H
D
D

LM34
Y10
D
Y11
D
Y10
D
Y12
D
D
D

LM35
X1
H
X4
H
X1
H
H
H
H
D

LM36
X1
H
X4
H
X1
H
H
H
D
H

LM37
X1
H
X4
H
X1
H
H
H
D
D

LM38
Y1
H
X4
H
Y1
H
H
H
D
D

LM39
Y2
H
X4
H
Y2
H
H
H
D
D

LM40
Y3
H
X4
H
Y3
H
H
H
D
D

LM41
Y3
D
X4
D
Y3
H
H
H
D
D

LM42
Y3
D
X4
D
Y3
D
H
H
D
D

LM43
Y3
D
X4
D
Y3
D
D
H
D
D

LM44
Y3
D
X4
D
Y3
D
D
D
D
D

LM45
Y3
D
Y12
D
Y3
D
D
D
D
D

LM46
Y3
D
Y12
D
Y3
H
X1
H
D
D

LM47
Y3
D
Y12
D
Y3
D
Y3
D
D
D

LM48
Y3
D
Y12
D
Y3
H
X4
H
D
D

LM49
Y3
D
Y12
D
Y3
D
Y12
D
D
D

LM50
X2
H
X4
H
X2
H
H
H
H
D

LM51
X2
H
X4
H
X2
H
H
H
D
H

LM52
X2
H
X4
H
X2
H
H
H
D
D

LM53
Y4
H
X4
H
Y4
H
H
H
D
D

LM54
Y5
H
X4
H
Y5
H
H
H
D
D

LM55
Y6
H
X4
H
Y6
H
H
H
D
D

LM56
Y7
H
X4
H
Y7
H
H
H
D
D

LM57
Y8
H
X4
H
Y8
H
H
H
D
D

LM58
Y9
H
X4
H
Y9
H
H
H
D
D

LM59
Y10
H
X4
H
Y10
H
H
H
D
D

LM60
Y10
D
X4
D
Y10
H
H
H
D
D

LM61
Y10
D
X4
D
Y10
D
H
H
D
D

LM62
Y10
D
X4
D
Y10
D
D
H
D
D

LM63
Y10
D
X4
D
Y10
D
D
D
D
D

LM64
Y10
D
Y12
D
Y10
D
D
D
D
D

LM65
Y10
D
Y12
D
Y10
H
X1
H
D
D

LM66
Y10
D
Y12
D
Y10
D
Y3
D
D
D

LM67
Y10
D
Y12
D
Y10
H
X4
H
D
D

LM68
Y10
D
Y12
D
Y10
D
Y12
D
D
D

LM69
X1
H
X5
H
X1
H
H
H
H
D

LM70
X1
H
X5
H
X1
H
H
H
D
H

LM71
X1
H
X5
H
X1
H
H
H
D
D

LM72
Y1
H
X5
H
Y1
H
H
H
D
D

LM73
Y2
H
X5
H
Y2
H
H
H
D
D

LM74
Y3
H
X5
H
Y3
H
H
H
D
D

LM75
Y3
D
X5
D
Y3
H
H
H
D
D

LM76
Y3
D
X5
D
Y3
D
H
H
D
D

LM77
Y3
D
X5
D
Y3
D
D
H
D
D

LM78
Y3
D
X5
D
Y3
D
D
D
D
D

LM79
Y3
D
Y13
D
Y3
D
D
D
D
D

LM80
Y3
D
Y13
D
Y3
H
X1
H
D
D

LM81
Y3
D
Y13
D
Y3
D
Y3
D
D
D

LM82
Y3
D
Y13
D
Y3
H
X4
H
D
D

LM83
Y3
D
Y13
D
Y3
D
Y12
D
D
D

LM84
X2
H
X5
H
X2
H
H
H
H
D

LM85
X2
H
X5
H
X2
H
H
H
D
H

LM86
X2
H
X5
H
X2
H
H
H
D
D

LM87
Y4
H
X5
H
Y4
H
H
H
D
D

LM88
Y5
H
X5
H
Y5
H
H
H
D
D

LM89
Y6
H
X5
H
Y6
H
H
H
D
D

LM90
Y7
H
X5
H
Y7
H
H
H
D
D

LM91
Y8
H
X5
H
Y8
H
H
H
D
D

LM92
Y9
H
X5
H
Y9
H
H
H
D
D

LM93
Y10
H
X5
H
Y10
H
H
H
D
D

LM94
Y10
D
X5
D
Y10
H
H
H
D
D

LM95
Y10
D
X5
D
Y10
D
H
H
D
D

LM96
Y10
D
X5
D
Y10
D
D
H
D
D

LM97
Y10
D
X5
D
Y10
D
D
D
D
D

LM98
Y10
D
Y13
D
Y10
D
D
D
D
D

LM99
Y10
D
Y13
D
Y10
H
X1
H
D
D

LM100
Y10
D
Y13
D
Y10
D
Y3
D
D
D

LM101
Y10
D
Y13
D
Y10
H
X4
H
D
D

LM102
Y10
D
Y13
D
Y10
D
Y12
D
D
D

LM103
X1
H
X6
H
X1
H
H
H
H
D

LM104
X1
H
X6
H
X1
H
H
H
D
H

LM105
X1
H
X6
H
X1
H
H
H
D
D

LM106
Y1
H
X6
H
Y1
H
H
H
D
D

LM107
Y2
H
X6
H
Y2
H
H
H
D
D

LM108
Y3
H
X6
H
Y3
H
H
H
D
D

LM109
Y3
D
X6
D
Y3
H
H
H
D
D

LM110
Y3
D
X6
D
Y3
D
H
H
D
D

LM111
Y3
D
X6
D
Y3
D
D
H
D
D

LM112
Y3
D
X6
D
Y3
D
D
D
D
D

LM113
Y3
D
Y14
D
Y3
D
D
D
D
D

LM114
Y3
D
Y14
D
Y3
H
X1
H
D
D

LM115
Y3
D
Y14
D
Y3
D
Y3
D
D
D

LM116
Y3
D
Y14
D
Y3
H
X4
H
D
D

LM117
Y3
D
Y14
D
Y3
D
Y12
D
D
D

LM118
X2
H
X6
H
X2
H
H
H
H
D

LM119
X2
H
X6
H
X2
H
H
H
D
H

LM120
X2
H
X6
H
X2
H
H
H
D
D

LM121
Y4
H
X6
H
Y4
H
H
H
D
D

LM122
Y5
H
X6
H
Y5
H
H
H
D
D

LM123
Y6
H
X6
H
Y6
H
H
H
D
D

LM124
Y7
H
X6
H
Y7
H
H
H
D
D

LM125
Y8
H
X6
H
Y8
H
H
H
D
D

LM126
Y9
H
X6
H
Y9
H
H
H
D
D

LM127
Y10
H
X6
H
Y10
H
H
H
D
D

LM128
Y10
D
X6
D
Y10
H
H
H
D
D

LM129
Y10
D
X6
D
Y10
D
H
H
D
D

LM130
Y10
D
X6
D
Y10
D
D
H
D
D

LM131
Y10
D
X6
D
Y10
D
D
D
D
D

LM132
Y10
D
Y14
D
Y10
D
D
D
D
D

LM133
Y10
D
Y14
D
Y10
H
X1
H
D
D

LM134
Y10
D
Y14
D
Y10
D
Y3
D
D
D

LM135
Y10
D
Y14
D
Y10
H
X4
H
D
D

LM136
Y10
D
Y14
D
Y10
D
Y12
D
D
D

LM137
X1
H
X7
H
X1
H
H
H
H
D

LM138
X1
H
X7
H
X1
H
H
H
D
H

LM139
X1
H
X7
H
X1
H
H
H
D
D

LM140
Y1
H
X7
H
Y1
H
H
H
D
D

LM141
Y2
H
X7
H
Y2
H
H
H
D
D

LM142
Y3
H
X7
H
Y3
H
H
H
D
D

LM143
Y3
D
X7
D
Y3
H
H
H
D
D

LM144
Y3
D
X7
D
Y3
D
H
H
D
D

LM145
Y3
D
X7
D
Y3
D
D
H
D
D

LM146
Y3
D
X7
D
Y3
D
D
D
D
D

LM147
Y3
D
X8
D
Y3
D
D
D
D
D

LM148
Y3
D
Y16
D
Y3
D
D
D
D
D

LM149
Y3
D
Y17
D
Y3
D
D
D
D
D

LM150
Y3
D
Y18
D
Y3
D
D
D
D
D

LM151
Y3
D
Y15
D
Y3
D
D
D
D
D

LM152
Y3
D
Y15
D
Y3
H
X1
H
D
D

LM153
Y3
D
Y15
D
Y3
D
Y3
D
D
D

LM154
Y3
D
Y16
D
Y3
D
Y3
D
D
D

LM155
Y3
D
Y17
D
Y3
D
Y3
D
D
D

LM156
Y3
D
Y18
D
Y3
D
Y3
D
D
D

LM157
Y3
D
Y15
D
Y3
H
X4
H
D
D

LM158
Y3
D
Y15
D
Y3
D
Y12
D
D
D

LM159
Y3
D
Y16
D
Y3
D
Y12
D
D
D

LM160
Y3
D
Y17
D
Y3
D
Y12
D
D
D

LM161
Y3
D
Y18
D
Y3
D
Y12
D
D
D

LM162
X2
H
X7
H
X2
H
H
H
H
D

LM163
X2
H
X7
H
X2
H
H
H
D
H

LM164
X2
H
X7
H
X2
H
H
H
D
D

LM165
Y4
H
X7
H
Y4
H
H
H
D
D

LM166
Y5
H
X7
H
Y5
H
H
H
D
D

LM167
Y6
H
X7
H
Y6
H
H
H
D
D

LM168
Y7
H
X7
H
Y7
H
H
H
D
D

LM169
Y8
H
X7
H
Y8
H
H
H
D
D

LM170
Y9
H
X7
H
Y9
H
H
H
D
D

LM171
Y10
H
X7
H
Y10
H
H
H
D
D

LM172
Y10
D
X7
D
Y10
H
H
H
D
D

LM173
Y10
D
X7
D
Y10
D
H
H
D
D

LM174
Y10
D
X7
D
Y10
D
D
H
D
D

LM175
Y10
D
X7
D
Y10
D
D
D
D
D

LM176
Y10
D
X8
D
Y10
D
D
D
D
D

LM177
Y10
D
Y16
D
Y10
D
D
D
D
D

LM178
Y10
D
Y17
D
Y10
D
D
D
D
D

LM179
Y10
D
Y18
D
Y10
D
D
D
D
D

LM180
Y10
D
Y15
D
Y10
D
D
D
D
D

LM181
Y10
D
Y15
D
Y10
H
X1
H
D
D

LM182
Y10
D
Y15
D
Y10
D
Y3
D
D
D

LM183
Y10
D
Y16
D
Y10
D
Y3
D
D
D

LM184
Y10
D
Y17
D
Y10
D
Y3
D
D
D

LM185
Y10
D
Y18
D
Y10
D
Y3
D
D
D

LM186
Y10
D
Y15
D
Y10
H
X4
H
D
D

LM187
Y10
D
Y15
D
Y10
D
Y12
D
D
D

LM188
Y10
D
Y16
D
Y10
D
Y12
D
D
D

LM189
Y10
D
Y17
D
Y10
D
Y12
D
D
D

LM190
Y10
D
Y18
D
Y10
D
Y12
D
D
D

LM191
X1
X7
H
H
X1
H
H
H
H
D

LM192
X1
X7
H
H
X1
H
H
H
D
H

LM193
X1
X7
H
H
X1
H
H
H
D
D

LM194
Y1
X7
H
H
Y1
H
H
H
D
D

LM195
Y2
X7
H
H
Y2
H
H
H
D
D

LM196
Y3
X7
H
H
Y3
H
H
H
D
D

LM197
Y3
X7
D
D
Y3
H
H
H
D
D

LM198
Y3
X7
D
D
Y3
D
H
H
D
D

LM199
Y3
X7
D
D
Y3
D
D
H
D
D

LM200
Y3
X7
D
D
Y3
D
D
D
D
D

LM201
Y3
Y15
D
D
Y3
D
D
D
D
D

LM202
Y3
Y16
D
D
Y3
D
D
D
D
D

LM203
Y3
Y17
D
D
Y3
D
D
D
D
D

LM204
Y3
Y18
D
D
Y3
D
D
D
D
D

LM205
Y3
Y15
D
D
Y3
H
X1
H
D
D

LM206
Y3
Y15
D
D
Y3
D
Y3
D
D
D

LM207
Y3
Y16
D
D
Y3
D
Y3
D
D
D

LM208
Y3
Y17
D
D
Y3
D
Y3
D
D
D

LM209
Y3
Y18
D
D
Y3
D
Y3
D
D
D

LM210
Y3
Y15
D
D
Y3
H
X4
H
D
D

LM211
Y3
Y15
D
D
Y3
D
Y12
D
D
D

LM212
Y3
Y16
D
D
Y3
D
Y12
D
D
D

LM213
Y3
Y17
D
D
Y3
D
Y12
D
D
D

LM214
Y3
Y18
D
D
Y3
D
Y12
D
D
D

LM215
X2
X7
H
H
X2
H
H
H
H
D

LM216
X2
X7
H
H
X2
H
H
H
D
H

LM217
X2
X7
H
H
X2
H
H
H
D
D

LM218
Y4
X7
H
H
Y4
H
H
H
D
D

LM219
Y5
X7
H
H
Y5
H
H
H
D
D

LM220
Y6
X7
H
H
Y6
H
H
H
D
D

LM221
Y7
X7
H
H
Y7
H
H
H
D
D

LM222
Y8
X7
H
H
Y8
H
H
H
D
D

LM223
Y9
X7
H
H
Y9
H
H
H
D
D

LM224
Y10
X7
H
H
Y10
H
H
H
D
D

LM225
Y10
X7
D
D
Y10
H
H
H
D
D

LM226
Y10
X7
D
D
Y10
D
H
H
D
D

LM227
Y10
X7
D
D
Y10
D
D
H
D
D

LM228
Y10
X7
D
D
Y10
D
D
D
D
D

LM229
Y10
X8
D
D
Y10
D
D
D
D
D

LM230
Y10
Y16
D
D
Y10
D
D
D
D
D

LM231
Y10
Y17
D
D
Y10
D
D
D
D
D

LM232
Y10
Y18
D
D
Y10
D
D
D
D
D

LM233
Y10
Y15
D
D
Y10
D
D
D
D
D

LM234
Y10
Y15
D
D
Y10
H
X1
H
D
D

LM235
Y10
Y15
D
D
Y10
D
Y3
D
D
D

LM236
Y10
Y16
D
D
Y10
D
Y3
D
D
D

LM237
Y10
Y17
D
D
Y10
D
Y3
D
D
D

LM238
Y10
Y18
D
D
Y10
D
Y3
D
D
D

LM239
Y10
Y15
D
D
Y10
H
X4
H
D
D

LM240
Y10
Y15
D
D
Y10
D
Y12
D
D
D

LM241
Y10
Y16
D
D
Y10
D
Y12
D
D
D

LM242
Y10
Y17
D
D
Y10
D
Y12
D
D
D

LM243
Y10
Y18
D
D
Y10
D
Y12
D
D
D

TABLE 6

Formula 1-2

Ligand

name
R₁₁
X₁₁
R₁₀₁
R₁₀₂
R₁₀₃
R₁₀₄
R₁₄
R₁₅
R₁₆
R₁₇
R₁₈
R₁₉
R₂₀

LFM1
Y10
N-Ph
D
D
D
D
D
Y10
D
D
D
D
D

LFM2
Y10
S
D
D
D
D
D
Y10
D
D
D
D
D

LFM3
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFM4
Y3
O
D
D
D
D
D
Y3
D
D
D
D
D

LFM5
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFM6
Y10
O
D
D
D
D
D
Y10
D
Y3
D
D
D

LFM7
Y10
O
D
D
D
D
D
Y10
D
Y12
D
D
D

TABLE 7

Formula 1-3

Ligand

name
R₁₁
X₁₁
R₁₀₁
R₁₀₂
R₁₀₃
R₁₀₄
R₁₄
R₁₅
R₁₆
R₁₇
R₁₈
R₁₉
R₂₀

LFP1
Y10
N-Ph
D
D
D
D
D
Y10
D
D
D
D
D

LFP2
Y10
S
D
D
D
D
D
Y10
D
D
D
D
D

LFP3
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFP4
Y3
O
D
D
D
D
D
Y3
D
D
D
D
D

LFP5
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFP6
Y10
O
D
D
D
D
D
Y10
D
Y3
D
D
D

LFP7
Y10
O
D
D
D
D
D
Y10
D
Y12
D
D
D

X1 to X10 and Y1 to Y18 in Tables 5-7 are the same as described below, and Ph in the tables refers to a phenyl group:

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In an embodiment, the sensitizer may be represented by Formula 101 or 102, and in this case, the sensitizer may be referred to as a delayed fluorescence sensitizer:

[Image Omitted]

wherein, in Formulae 101 and 102,

A₂₁may be an acceptor group,

D₂₁may be a donor group,

m21 may be 1, 2, or 3, and n21 may be 1, 2, or 3,

the sum of n21 and m21 in Formula 101 may be 6 or less, and the sum of n21 and m21 in Formula 102 may be 5 or less,

R₂₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₇-C₆₀alkyl aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀alkyl heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), or —P(═S)(Q₁)(Q₂), and a plurality of R₂₁(s) may optionally be bonded together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, and

Q₁to Q₃may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof, or a C₆-C₆₀aryl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof.

In an embodiment, in Formulae 101 and 102, A₂₁may be a substituted or unsubstituted π electron-deficient nitrogen-free cyclic group.

In an embodiment, the π electron-deficient nitrogen-free cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group; or a condensed cyclic group of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the disclosure are not limited thereto.

In an embodiment, in Formulae 101 and 102, D₂₁may be: —F, a cyano group, or π electron-deficient nitrogen-containing cyclic group;

a C₁-C₆₀alkyl group, a π electron-deficient nitrogen-containing cyclic group, or a π electron-deficient nitrogen-free cyclic group, each substituted with at least one —F, a cyano group, a combination thereof; or

a π electron-deficient nitrogen-containing cyclic group, each substituted with at least one deuterium, a C₁-C₆₀alkyl group, a π electron-deficient nitrogen-containing cyclic group, a π electron-deficient nitrogen-free cyclic group, or a combination thereof.

In an embodiment, the π electron-deficient nitrogen-free cyclic group is the same as described above.

The term “π electron-deficient nitrogen-containing cyclic group” used herein refers to a cyclic group having at least one *—N═*′ moiety, and, for example, may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, and a benzimidazolobenzimidazole group; and a condensed cyclic group in which two or more π electron-efficient nitrogen-containing cyclic groups are condensed with each other.

In an embodiment, the sensitizer may be of Groups XI to XV, but embodiments of the disclosure are not limited thereto:

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Hole Transport Region 12

The hole transport region 12 may be located between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.

The hole transport region 12 may have a single-layered structure or a multi-layered structure.

For example, the hole transport region 12 may have a hole injection layer, a hole transport layer, a hole injection layer/hole transport layer structure, a hole injection layer/first hole transport layer/second hole transport layer structure, a hole transport layer/interlayer structure, a hole injection layer/hole transport layer/interlayer structure, a hole transport layer/electron blocking layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, but embodiments of the disclosure are not limited thereto.

The hole transport region 12 may include any compound having hole-transporting properties.

For example, the hole transport region 12 may include an amine-based compound.

In an embodiment, the hole transport region 1 may include at least one a compound represented by Formula 201 to a compound represented by Formula 205, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

wherein, in Formulae 201 to 205,

L₂₀₁to L₂₀₉may each independently *-be O—*′, *—S—*′, a substituted or unsubstituted C₅-C₆₀carbocyclic group, or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xa1 to xa9 may each independently be an integer from 0 to 5, and

R₂₀₁to R₂₀₆may each independently be a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and two neighboring groups of R₂₀₁to R₂₀₆may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

In an embodiment, L₂₀₁to L₂₀₉may be a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —Si(Q₁₁)(Q₁₂)(Q₁₃), or a combination thereof,

xa1 to xa9 may each independently be 0, 1, or 2, and

R₂₀₁to R₂₀₆may each independently be a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, or a benzothienocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), or a combination thereof,

wherein Q₁₁to Q₁₃and Q₃₁to Q₃₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In an embodiment, the hole transport region 12 may include a carbazole-containing amine-based compound.

In an embodiment, the hole transport region 12 may include a carbazole-containing amine-based compound and a carbazole-free amine-based compound.

The carbazole-containing amine-based compound may be, for example, a compound represented by Formula 201 including a carbazole group and further including at least one a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, or a benzothienocarbazole group.

The carbazole-free amine-based compound may be, for example, a compound represented by Formula 201 which do not include a carbazole group and which include at least one a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a combination thereof.

In an embodiment, the hole transport region 12 may include at least one compound represented by Formulae 201 or 202.

In an embodiment, the hole transport region 12 may include at least one compound represented by Formulae 201-1, 202-1 or 201-2, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

In Formulae 201-1, 202-1, and 201-2, L₂₀₁to L₂₀₃, L₂₀₅, xa1 to xa3, xa5, R₂₀₁and R₂₀₂are the same as described herein, and R₂11 to R₂₁₃are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenyl fluorenyl group, a triphenylenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, or a combination thereof.

For example, the hole transport region 12 may include at least one of Compounds HT1 to HT39, but embodiments of the disclosure are not limited thereto.

[Image Omitted]

In an embodiment, the hole transport region may include at least one compound 4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC) and tris(4-carbazoyl-9-ylphenyl)amine (TCTA).

In an embodiment, hole transport region 12 of the organic light-emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (for example, at least one of compounds represented by Formulae 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.

In an embodiment, the LUMO energy level of the p-dopant may be about −3.5 eV or less.

The p-dopant may include at least one a quinone derivative, a metal oxide, a cyano group-containing compound, or a combination thereof, but embodiments of the disclosure are not limited thereto.

In an embodiment, the p-dopant may include at least one:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and F6-TCNNQ;

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN);

a compound represented by Formula 221 below, or a combination thereof,

but embodiments of the disclosure are not limited thereto:

[Image Omitted]

In Formula 221, R₂₂₁to R₂₂₃may each independently be a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one of R₂₂₁to R₂₂₃may have at least one substituent a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group substituted with —F, a C₁-C₂₀alkyl group substituted with —Cl, a C₁-C₂₀alkyl group substituted with —Br, a C₁-C₂₀alkyl group substituted with —I, or a combination thereof.

The hole transport region 12 may have a thickness of about 100 Å to about 10000 Å, for example, about 400 Å to about 2000 Å, and the emission layer 15 may have a thickness of about 100 Å to about 3000 Å, for example, about 300 Å to about 1000 Å. When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges described above, satisfactory hole transportation characteristics and/or luminescent characteristics may be obtained without a substantial increase in driving voltage.

Electron Transport Region 17

The electron transport region 17 is placed between the emission layer 15 and the second electrode 19 of the organic light-emitting device 10.

The electron transport region 17 may have a single-layered structure or a multi-layered structure.

For example, the electron transport region 17 may have an electron transport layer, an electron transport layer/electron injection layer structure, a buffer layer/electron transport layer structure, hole blocking layer/electron transport layer structure, a buffer layer/electron transport layer/electron injection layer structure, or a hole blocking layer/electron transport layer/electron injection layer structure, but embodiments of the disclosure are not limited thereto. The electron transport region 17 may further include an electron control layer.

The electron transport region 17 may include known electron-transporting materials.

The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-deficient nitrogen-containing cyclic group. The π electron-deficient nitrogen-containing cyclic group is the same as described above.

In an embodiment, the electron transport region may include a compound represented by Formula 601 below:

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21 Formula 601

wherein, in Formula 601,

Ar₆₀₁and L₆₀₁may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xe11 may be 1, 2, or 3,

xe1 is an integer from 0 to 5,

R₆₀₁may be a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and

xe21 is an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 and R₆₀₁(s) in the number of xe21 may include the π electron-deficient nitrogen-containing cyclic group.

In one embodiment, ring Ar₆₀₁and L₆₀₁in Formula 601 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or a combination thereof,

wherein Q₃₁to Q₃₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more of Ar₆₀₁(s) may be linked to each other via a single bond.

In an embodiment, Ar₆₀₁in Formula 601 may be an anthracene group.

In an embodiment, the compound represented by Formula 601 may be represented by Formula 601-1:

[Image Omitted]

wherein, in Formula 601-1,

X₆₁₄may be N or C(R₆₁₄), X₆₁₅may be N or C(R₆₁₅), X₆₁₆may be N or C(R₆₁₆), at least one of X₆₁₄to X₆₁₆may be N,

L₆₁₁to L₆₁₃may each independently be the same as described in connection with L₆₀₁,

xe611 to xe613 may each independently be the same as described in connection with xe1,

R₆₁₁to R₆₁₃may each independently be the same as described in connection with R₆₀₁, and

R₆₁₄to R₆₁₆may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In an embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.

In an embodiment, R₆₀₁and R₆₁₁to R₆₁₃in Formulae 601 and 601-1 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, or a combination thereof; or

—S(═O)₂(Q₆₀₁) or —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁and Q₆₀₂are the same as described above.

The electron transport region may include at least one of Compounds ET1 to ET36, but embodiments of the disclosure are not limited thereto:

[Image Omitted]

In an embodiment, the electron transport region may include at least one compound of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi), NTAZ, or a combination thereof.

[Image Omitted]

Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in the range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in the range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.

The electron transport region 17 (for example, the electron transport layer in the electron transport region 17) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include at least one alkali metal complex, alkaline earth-metal complex, or a combination thereof. The alkali metal complex may include a metal ion including a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the alkaline earth-metal complex may include a metal ion including a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, or a cyclopentadiene, but embodiments of the disclosure are not limited thereto.

In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:

[Image Omitted]

The electron transport region 17 may include an electron injection layer that facilitates the injection of electrons from the second electrode 19. The electron injection layer may directly contact the second electrode 19.

The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.

The alkali metal may be Li, Na, K, Rb, or Cs. In an embodiment, the alkali metal may be Li, Na, or Cs. In an embodiment, the alkali metal may be Li or Cs, but embodiments of the disclosure are not limited thereto.

The alkaline earth metal may be Mg, Ca, Sr, or Ba.

The rare earth metal may be Sc, Y, Ce, Tb, Yb, or Gd.

The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be an oxide or a halide (for example, fluoride, chloride, bromide, or iodide) of the alkali metal, the alkaline earth-metal, or the rare earth metal.

The alkali metal compound may be an alkali metal oxide, such as Li₂O, Cs₂O, or K₂O, or an alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In an embodiment, the alkali metal compound may be LiF, Li₂O, NaF, LiI, NaI, CsI, or KI, but embodiments of the disclosure are not limited thereto.

The alkaline earth-metal compound may be an alkaline earth-metal oxide, such as BaO, SrO, CaO, Ba_xSr_1-xO (0<x<1), or Ba_xCa_1-xO (0<x<1). In an embodiment, the alkaline earth-metal compound may be BaO, SrO, or CaO, but embodiments of the disclosure are not limited thereto.

The rare earth metal compound may be YbF₃, ScF₃, ScO₃, Y₂O₃, Ce₂O₃, GdF₃, or TbF₃. In an embodiment, the rare earth metal compound may be YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, or TbI₃, but embodiments of the disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of an alkali metal, an alkaline earth-metal, or a rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, or cyclopentadiene, but embodiments of the disclosure are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In an embodiment, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

Second Electrode 19

The second electrode 19 is located on the organic layer 10A having such a structure. The second electrode 19 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, which has a relatively low work function.

The second electrode 19 may include at least one lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, IZO, or a combination thereof, but embodiments of the disclosure are not limited thereto. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 19 may have a single-layered structure having a single layer or a multi-layered structure including two or more layers.

Hereinbefore, the organic light-emitting device has been described with reference to FIG. 1, but embodiments of the disclosure are not limited thereto.

Description of FIG. 2

FIG. 2 is a schematic view of a cross-section of an organic light-emitting device 100 according to another exemplary embodiment.

The organic light-emitting device 100 of FIG. 2 includes a first electrode 110, a second electrode 190 facing the first electrode 110, and a first emitting unit 151 and a second emitting unit 152 between the first electrode 110 and the second electrode 190. A charge generation layer 141 is located between the first emitting unit 151 and the second emitting unit 152, and the charge generation layer 141 may include an n-type charge generation layer 141-N and a p-type charge generation layer 141-P. The charge generation layer 141 is a layer that generates charge and supplies the charge to neighboring emitting units, and any known material may be used therefor.

The first emitting unit 151 may include a first emission layer 151-EM, and the second emitting unit 152 may include a second emission layer 152-EM. The maximum emission wavelength of light emitted from the first emitting unit 151 may be different from the maximum emission wavelength of light emitted from the second emitting unit 152. For example, the mixed light including the light emitted from the first emitting unit 151 and the light emitted from the second emitting unit 152 may be white light, but embodiments of the disclosure are not limited thereto.

The hole transport region 120 is located between the first emitting unit 151 and the first electrode 110, and the second emitting unit 152 may include the first hole transport region 121 located on the side of the first electrode 110.

An electron transport region 170 is located between the second emitting unit 152 and the second electrode 190, and the first emitting unit 151 may include a first electron transport region 171 located between the charge generation layer 141 and the first emission layer 151-EM.

The first emission layer 151-EM may include the heterocyclic compound.

The second emission layer 152-EM may include the heterocyclic compound.

The first electrode 110 and the second electrode 190 illustrated in FIG. 2 may be the same as described in connection with the first electrode 11 and the second electrode 19 illustrated in FIG. 1.

The first emission layer 151-EM and the second emission layer 152-EM in FIG. 2 are respectively the same as described in connection with the emission layer 15 in FIG. 1.

The hole transport region 120 and the first hole transport region 121 illustrated in FIG. 2 are each the same as described in connection with the hole transport region 12 illustrated in FIG. 1.

The electron transport region 170 and the first electron transport region 171 illustrated in FIG. 2 are each the same as described in connection with the electron transport region 17 illustrated in FIG. 1.

As described above, referring to FIG. 2, an organic light-emitting device in which each of the first emitting unit 151 and the second emitting unit 152 includes an emission layer including a host, a dopant, and a sensitizer, has been described. However, the organic light-emitting device may have various other forms. For example, one of the first emitting unit 151 and the second emitting unit 152 of the organic light-emitting device 100 of FIG. 2 may be replaced with any known emitting unit, or may include three or more emitting units.

Description of FIG. 3

FIG. 3 is a schematic cross-sectional view of an organic light-emitting device 200 according to another exemplary embodiment.

The organic light-emitting device 200 includes a first electrode 210, a second electrode 290 facing the first electrode 210, and a first emission layer 251 and a second emission layer 252 which are stacked between the first electrode 210 and the second electrode 290.

The maximum emission wavelength of light emitted from the first emission layer 251 may be different from the maximum emission wavelength of light emitted from the second emission layer 252. For example, the mixed light of the light emitted from the first emission layer 251 and the light emitted from the second emission layer 252 may be white light, but embodiments of the disclosure are not limited thereto.

In an embodiment, a hole transport region 220 may be located between the first emission layer 251 and the first electrode 210, and an electron transport region 270 may be located between the second emission layer 252 and the second electrode 290.

The first emission layer 251 may include the heterocyclic compound.

The second emission layer 252 may include the heterocyclic compound.

The first electrode 210, the hole transport region 220, and the second electrode 290 illustrated in FIG. 3 are respectively the same as described in connection with the first electrode 11, the hole transport region 12, and the second electrode 19 illustrated in FIG. 1.

The first emission layer 251 and the second emission layer 252 illustrated in FIG. 3 are each the same as described in connection with the emission layer 15 illustrated in FIG. 1.

The electron transport region 270 illustrated in FIG. 3 may be the same as described in connection with the electron transport region 17 in FIG. 1.

Hereinbefore, referring to FIG. 3, although the organic light-emitting device including the heterocyclic compound is described, various modifications are available, for example, one of the first emission layer 251 and the second emission layer 252 in FIG. 3 may be replaced with a known layer, the organic light-emitting device may include three or more emission layers, or an interlayer may be additionally arranged between neighboring emission layers.

Electronic Apparatus

The organic light-emitting device may be included in various electronic apparatuses.

The electronic apparatus may further include a thin-film transistor in addition to the organic light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device.

Explanation of Terms

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

The term “C₁-C₆₀alkoxy group” used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₆₀alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C₁-C₂₀alkylthio group” as used herein refers to a monovalent group represented by —SA₁₀₂(wherein A₁₀₂is the C₁-C₂₀alkyl group), and non-limiting examples thereof include a methylthio group, an ethylthio group, and an iso-propylthio group.

The term “C₂-C₆₀alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₆₀alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkenyl group.

The term “C₂-C₆₀alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₆₀alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkynyl group.

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C₃-C₁₀cycloalkylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

The term “a (C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms attached to an alkylene group. A non-limiting example includes a —CH₂-cyclopropyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom including N, O, P, Si, S, Se, Ge, Te, B, or a combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom including N, O, P, Si, S, Se, Ge, Te, B, or a combination thereof as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused to each other.

The terms “a (C₁-C₂₀alkyl)phenyl group” and “(C₁-C₂₀alkyl)biphenyl group” refer to a monovalent phenyl group or biphenyl group, respectively, attached to an alkylene group. A non-limiting example of a (C₁-C₂₀alkyl)phenyl group includes a —CH₂-phenyl group A non-limiting example of a (C₁-C₂₀alkyl)biphenyl group includes a —CH₂-biphenyl group

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocarbocyclic aromatic system that has at least one heteroatom including N, O, P, Si, S, Se, Ge, Te, B, or a combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom including N, O, P, S, Se, Ge, Te, B, or a combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₆-C₆₀heteroaryl group and the C₆-C₆₀heteroarylene group each include two or more rings, the rings may be fused to each other.

The term “C₆-C₆₀aryloxy group” as used herein indicates —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group” as used herein indicates —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group).

The term “monovalent aromatic condensed polycyclic group” as used herein refers to a monovalent group having two or more rings condensed with each other, including only carbon atoms (for example, the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, and having aromaticity in its molecular structure when considered as a whole. The term “divalent aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent aromatic condensed polycyclic group.

The term “monovalent aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having at least two rings condensed with each other, including a heteroatom including N, O, P, Si, S, Se, Ge, Te, B, or a combination thereof as well as carbon atoms (for example, the number of carbon atoms may be in a range of 1 to 60) as ring-forming atoms, and having aromaticity in its molecular structure when considered as a whole. The term “divalent aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent aromatic condensed heteropolycyclic group.

The term “monovalent non-aromatic condensed polycyclic group” used herein refers to a monovalent group having two or more rings condensed with each other, including only carbon atoms (for example, the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, and having aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed with each other, including a heteroatom including N, O, P, Si, S Se, Ge, Te, B, or a combination thereof, other than carbon atoms (for example, the number of carbon atoms may be in a range of 1 to 60) as ring-forming atoms, and having no aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

The term “π electron-depleted nitrogen-containing C₁-C₆₀cyclic group” as used herein refers to a cyclic group having 1 to 60 carbon atoms and including at least one *—N═*′ (wherein * and *′ each indicate a binding site to an adjacent atom) as a ring-forming moiety. For example, the π electron-depleted nitrogen-containing C₁-C₆₀cyclic group may be a) a first ring, b) a condensed ring in which at least two first rings are condensed, or c) a condensed ring in which at least one first ring and at least one second ring are condensed.

The term “π electron-rich C₃-C₆₀cyclic group” as used herein refers to a cyclic group having 3 to 60 carbon atoms and not including at least one *—N═*′ (wherein * and *′ each indicate a binding site to an adjacent atom) as a ring-forming moiety. For example, the π electron-rich C₃-C₆₀cyclic group may be a) a second ring or b) a condensed ring in which at least two second rings are condensed.

The term “C₅-C₆₀carbocyclic group” as used herein refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, and may be, for example, a) a third ring or b) a condensed ring in which two or more third rings are condensed with each other.

The term “C₁-C₆₀heterocyclic group” as used herein refers to a monocyclic or polycyclic group that has 1 to 60 carbon atoms and includes at least one heteroatom, and may be, for example, a) a fourth ring, b) a condensed ring in which two or more fourth rings are condensed with each other, or c) a condensed ring in which at least one third ring is condensed with at least one fourth ring.

The “first ring” as used herein may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, or a thiadiazole group.

The “second ring” as used herein may be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group.

The “third ring” as used herein may be a cyclopentane group, a cyclopentadiene group, an indene group, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (a norbornane group), a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, or a benzene group.

The “fourth ring” as used herein may be a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, a triazasilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

In an embodiment, the π electron-depleted nitrogen-containing C₁-C₆₀cyclic group may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an acridine group, or a pyridopyrazine group:

In an embodiment, the π electron-rich C₃-C₆₀cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, a pyrrolophenanthrene group, a furanophenanthrene group, a thienophenanthrene group, a benzonaphthofuran group, a benzonapthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothieno)phenanthrene group.

For example, the C₅-C₆₀carbocyclic group may be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, an indene group, a fluorene group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

For example, the C₁-C₆₀heterocyclic group may be a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group.

The term “a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group, a π electron-rich C₃-C₆₀cyclic group, a C₅-C₆₀cyclic group, and a C₁-C₆₀heterocyclic group” may be part of a condensed cycle or may be a monovalent, a divalent, a trivalent, a tetravalent, a pentavalent, or a hexavalent group, depending on the formula structure.

In the present specification, at least one substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₁-C₃₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent aromatic condensed polycyclic group, the substituted monovalent aromatic condensed heteropolycyclic group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or a combination thereof;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or a combination thereof; or

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), or —P(═O)(Q₃₈)(Q₃₉),

wherein Q₁to Q, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryl group substituted with at least one a C₁-C₆₀alkyl group and a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

As used herein, the number of carbons in each group that is substituted (e.g., C₁-C₆₀) excludes the number of carbons in the substituent. For example, a C₁-C₆₀alkyl group can be substituted with a C₁-C₆₀alkyl group. The total number of carbons included in the C₁-C₆₀alkyl group substituted with the C₁-C₆₀alkyl group is not limited to 60 carbons. In addition, more than one C₁-C₆₀alkyl substituent may be present on the C₁-C₆₀alkyl group. This definition is not limited to the C₁-C₆₀alkyl group and applies to all substituted groups that recite a carbon range.

The term “room temperature” used herein refers to a temperature of about 25° C.

The terms “a biphenyl group, a terphenyl group, and a tetraphenyl group” used herein respectively refer to monovalent groups in which two, three, or four phenyl groups which are linked together via a single bond.

The terms “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing tetraphenyl group” used herein respectively refer to a phenyl group, a biphenyl group, a terphenyl group, and a tetraphenyl group, each of which is substituted with at least one cyano group. In “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing tetraphenyl group”, a cyano group may be substituted to any position of the corresponding group, and the “cyano-containing phenyl group, the cyano-containing biphenyl group, the cyano-containing terphenyl group, and the cyano-containing tetraphenyl group” may further include substituents other than a cyano group. For example, a phenyl group substituted with a cyano group, and a phenyl group substituted with a cyano group and a methyl group may all belong to “a cyano-containing phenyl group.”

Hereinafter, a compound and an organic light-emitting device according to embodiments are described In an embodiment with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The wording “‘B’ was used instead of ‘A’” used in describing Synthesis Examples means that an amount of ‘A’ used was identical to an amount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 619

[Image Omitted]

Synthesis of Intermediate (A)

10.33 g (15.06 mmol) of bis(3-(triphenylsilyl)phenyl)amine, 5.22 g (15.06 mmol) of 9-(3,4,5-trichlorophenyl)-9H-carbazole, 0.43 g (0.75 mmol) of Bis(dibenzylideneacetone)palladium(0), 2.17 g (22.59 mmol) of sodium tert-butoxide, and 0.62 g (1.51 mmol) of SPhos were dissolved in 75 ml of toluene and then stirred for 2 hours at 110° C. The mixture was cooled to room temperature, and an organic layer was extracted and separated by using dichloromethane. By using magnesium sulfate, water was removed from the recovered organic layer, which was then filtered under reduced pressure. A filtrate thus obtained was separated by silica gel column chromatography to obtain 7.01 g (yield: 47%) of Intermediate (A) which is a target compound.

LC-Mass (calculated: 994 g/mol. found: M+1=995 g/mol.)

Synthesis of Intermediate (B)

6.72 g (6.75 mmol) of Intermediate (A), 3.70 g (7.08 mmol) of N-(3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-[1,1′-biphenyl]-4-amine, 0.62 g (0.67 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.97 g (10.12 mmol) of sodium tert-butoxide, and 0.28 g (0.67 mmol) of SPhos were dissolved in 68 ml of xylenes and then stirred for 10 minutes at 130° C. After the reaction is terminated, the mixture was cooled to room temperature, followed by adding methanol thereto, stirring for an hour, and then filtering under reduced pressure. A solid thus recovered was dried and then separated by silica gel column chromatography to obtain 5.10 g (yield: 51%) of Intermediate (B) which is a target compound.

LC-Mass (calculated: 1,480 g/mol. found: M+1=1,481 g/mol.)

Synthesis of Compound 619

5.09 g (3.43 mmol) of Intermediate (B) was dissolved in 70 ml of t-butylbenzene and then cooled to −70° C. 5.05 ml (8.59 mmol) of tert-butyllithium solution (1.7M in pentane) was added thereto, followed by stirring for an hour at 40° C., and then the mixture was cooled to −10° C. 0.66 ml (6.87 mmol) of boron tribromide was added thereto, followed by stirring for an hour at room temperature, and then the mixture was cooled to −10° C. 1.17 ml (6.87 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring for 4 hours at 120° C. After the reaction was completed, the mixture was cooled to −10° C., quenching was performed by using a sodium acetate solution, and an organic layer was extracted and separated by using toluene. By using magnesium sulfate, water was removed from the recovered organic layer, which was then filtered under reduced pressure. A filtrate thus obtained was separated by silica gel column chromatography to obtain 0.70 g (yield: 14%) of Compound 619.

LC-Mass (calculated: 1,454 g/mol. found: M+1=1,455 g/mol.)

Synthesis Example 2: Synthesis of Compound 620

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Synthesis of Intermediate (C)

3,6-di-tert-butyl-9-(3,4,5-trichlorophenyl)-9H-carbazole was used instead of 9-(3,4,5-trichlorophenyl)-9H-carbazole in the synthesis of Intermediate (A). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (A) to obtain 7.62 g (yield: 51%) of Intermediate (C) which is a target compound.

LC-Mass (calculated: 1,106 g/mol. found: M+1=1,107 g/mol.)

Synthesis of Intermediate (D)

Intermediate (C) was used instead of Intermediate (A) in the synthesis of Intermediate (B). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (B) to obtain 5.74 g (yield: 57%) of Intermediate (D) which is a target compound.

LC-Mass (calculated: 1,592 g/mol. found: M+1=1,593 g/mol.)

Synthesis of Compound 620

Intermediate (D) was used instead of Intermediate (B) in the synthesis of Compound 619. Synthesis and purification methods were performed in the same manner as used to synthesize Compound 619 to obtain 0.57 g (yield: 11%) of Compound 620.

LC-Mass (calculated: 1,566 g/mol. found: M+1=1,567 g/mol.)

Synthesis Example 3: Synthesis of Compound 126

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Synthesis of Intermediate (E)

Bis(4-(triphenylsilyl)phenyl)amine was used instead of bis(3-(triphenylsilyl)phenyl)amine in the synthesis of Intermediate (A). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (A) to obtain 16.30 g (yield: 54%) of Intermediate (E) which is a target compound.

LC-Mass (calculated: 994 g/mol. found: M+1=995 g/mol.)

Synthesis of Intermediate (F)

Intermediate (E) and diphenylamine were respectively used instead of Intermediate (A) and N-(3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-[1,1′-biphenyl]-4-amine in the synthesis of Intermediate (B). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (B) to obtain 4.42 g (yield: 55%) of Intermediate (F) which is a target compound.

LC-Mass (calculated: 1,127 g/mol. found: M+1=1,128 g/mol.)

Synthesis of Compound 126

Intermediate (F) was used instead of Intermediate (B) in the synthesis of Compound 619. Synthesis and purification methods were performed in the same manner as used to synthesize Compound 619 to obtain 0.39 g (yield: 10%) of Compound 126.

LC-Mass (calculated: 1,101 g/mol. found: M+1=1,102 g/mol.)

Synthesis Example 4: Synthesis of Compound 142

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Synthesis of Intermediate (G)

Intermediate (E) and di([1,1′-biphenyl]-4-yl)amine were respectively used instead of Intermediate (A) and N-(3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-[1,1′-biphenyl]-4-amine in the synthesis of Intermediate (B). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (B) to obtain 6.13 g (yield: 61%) of Intermediate (G) which is a target compound.

LC-Mass (calculated: 1,279 g/mol. found: M+1=1,280 g/mol.)

Synthesis of Compound 142

Intermediate (G) was used instead of Intermediate (B) in the synthesis of Compound 619. Synthesis and purification methods were performed in the same manner as used to synthesize Compound 619 to obtain 0.85 g (yield: 15%) of Compound 142.

LC-Mass (calculated: 1,253 g/mol. found: M+1=1,254 g/mol.)

Synthesis Example 5: Synthesis of Compound 83

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Synthesis of Intermediate (H)

12.98 g (25.76 mmol) of N-(4-(triphenylsilyl)phenyl)-[1,1′-biphenyl]-4-amine, 4.06 g (11.71 mmol) of 9-(3,4,5-trichlorophenyl)-9H-carbazole, 2.14 g (2.34 mmol) of tris(dibenzylideneacetone)dipalladium(0), 3.38 g (35.12 mmol) of sodium tert-butoxide, and 0.96 g (2.34 mmol) of SPhos were dissolved in 120 ml of xylenes and then stirred for 15 minutes at 130° C. After the reaction was terminated, the mixture was cooled to room temperature, followed by adding methanol thereto, stirring for an hour, and then filtering under reduced pressure. A solid thus recovered was dried and then separated by silica gel column chromatography to obtain 9.91 g (yield: 66%) of Intermediate (H) which is a target compound.

LC-Mass (calculated: 1,279 g/mol. found: M+1=1,280 g/mol.)

Synthesis of Compound 83

Intermediate (H) was used instead of Intermediate (B) in the synthesis of Compound 619. Synthesis and purification methods were performed in the same manner as used to synthesize Compound 619 to obtain 0.12 g (yield: 2%) of Compound 83.

LC-Mass (calculated: 1,253 g/mol. found: M+1=1,254 g/mol.)

Synthesis of Comparative Example Compound A

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Synthesis of Intermediate (I)

bis(4-(triphenylsilyl)phenyl)amine and 1-bromo-2,3-dichlorobenzene were respectively used instead of bis(3-(triphenylsilyl)phenyl)amine and 9-(3,4,5-trichlorophenyl)-9H-carbazole in the synthesis of Intermediate (A). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (A) to obtain 8.10 g (yield: 54%) of Intermediate (I) which is a target compound.

LC-Mass (calculated: 829 g/mol. found: M+1=830 g/mol.)

Synthesis of Intermediate (J)

Intermediate (I) was used instead of Intermediate (E) in the synthesis of Intermediate (G). Synthesis and purification methods were performed in the same manner as in the synthesis of Intermediate (G) to obtain 4.50 g (yield: 45%) of Intermediate (J) which is a target compound.

LC-Mass (calculated: 1,114 g/mol. found: M+1=1,115 g/mol.)

Synthesis of Compound A

Intermediate (J) was used instead of Intermediate (B) in the synthesis of Compound 619. Synthesis and purification methods were performed in the same manner as used to synthesize Compound 619 to obtain 0.08 g (yield: 2%) of Compound 83.

LC-Mass (calculated: 1,088 g/mol. found: M+1=1,089 g/mol.)

Example 1

An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm and then, sonicated in acetone isopropyl alcohol and pure water, each for 15 minutes, and then, washed by exposure of ultraviolet (UV) light ozone thereto for 30 minutes.

Subsequently, F6-TCNNQ was deposited on the ITO electrode (anode) on the glass substrate to form a hole injection layer having a thickness of 100 Å, and HT1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,260 Å, thereby completing the manufacture of a hole transport region.

Compound H-H1 (first host), H-E1 (second host), Compound S01 (sensitizer) (here, a weight ratio of the first host, the second host, and the sensitizer was 45:45:10), and Compound 619 (dopant) (here, an amount of the dopant was 0.1 parts by weight based on the total weight of the first host, the second host, the sensitizer, and the dopant) were co-deposited on the hole transport region to form an emission layer having a thickness of 400 Å.

Compound ET17 and Liq were co-deposited at a weight ratio of 5:5 on the emission layer to form an electron transport layer having a thickness of 360 Å, and then, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å, and Al was deposited on the electron injection layer to form a cathode having a thickness of 800 Å, thereby completing the manufacture of an organic light-emitting device.

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Examples 2 to 5 and Comparative Example 1

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming an emission layer, for use as a sensitizer and a dopant, the compounds shown in Table 8 were used.

Evaluation Example: Evaluation of OLED Characteristics

The driving voltage, maximum external quantum efficiency, and lifespan of the organic light-emitting devices manufactured in Examples and Comparative Example above were measured using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A), and results thereof are shown in Table 8. In this regard, the lifespan (T₉₅) was measured by the time that the luminance reaches 95% of the initial luminance (100%) at 1,000 nit. Each of values of the driving voltage, external quantum efficiency, and lifespan was expressed as a relative value based on a value of Comparative Example 1 as 100%.

TABLE 8

Driving
Lifespan

First
Second

voltage
(LT₉₅)
EQEmax

host
host
Sensitizer
Dopant
(%)
(%)
(%)

Example 1
H-H1
H-E1
S01
619
53
956
130

Example 2
H-H1
H-E1
S01
620
60
894
141

Example 3
H-H1
H-E1
S01
126
62
859
110

Example 4
H-H1
H-E1
S01
142
59
754
112

Example 5
H-H1
H-E1
S01
83
70
932
154

Comparative Example 1
H-H1
H-E1
S01
A
100
100
100

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Referring to Table 8, it may be seen that the organic light-emitting devices of Examples had higher efficiency and/or longer lifespan than those of the organic light-emitting device of Comparative Example.

As apparent from the foregoing description, an organic light-emitting device including the heterocyclic compound may have improved efficiency and/or colorimetric purity.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.