CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Applications Nos. 10-2021-0076312, filed on Jun. 11, 2021, and 10-2022-0070184, filed on Jun. 9, 2022, both in the Korean Intellectual Property Office, and all benefits accruing therefrom under 35 U.S.C. § 119, the entire contents of which are incorporated by reference herein.

BACKGROUND
1. Field

Provided are a composition, a layer including the composition, a light-emitting device including the composition, and an electronic apparatus including the light-emitting device.

2. Description of the Related Art

From among light-emitting devices, organic light-emitting devices (OLEDs) are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, luminance, driving voltage, and response speed, and produce full-color images.

In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located 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 to thereby generate light.

SUMMARY

Provided are a composition capable of providing excellent luminescence efficiency and lifespan characteristics and the like, a layer including the composition, a light-emitting device including the composition, an electronic apparatus including the 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 as described herein.

According to an aspect, provided is a composition including a first compound represented by Formula 1 and a second compound represented by Formula 2.

Ir(L₁₁)_n11(L₁₂)_n12(L₁₃)_n13 Formula 1

Ir(L₂₁)_n21(L₂₂)_n22(L₂₃)_n23 Formula 2

wherein, in Formulae 1 and 2,

L₁₁, L₁₂, L₁₃, L₂₁, L₂₂, and L₂₃are each:

i) a bidentate ligand bonded to iridium (Ir) of Formula 1 via two nitrogen atoms, or a bidentate ligand bonded to iridium of Formula 2 via two nitrogen atoms,

ii) a bidentate ligand bonded to iridium of Formula 1 via a nitrogen atom and a carbon atom, or a bidentate ligand bonded to iridium of Formula 2 via a nitrogen atom and a carbon atom, or

iii) a bidentate ligand bonded to iridium of Formula 1 via two carbon atoms, or a bidentate ligand bonded to iridium of Formula 2 via two carbon atoms,

L₁₁, L₁₂, and L₁₃are different from one another,

n11 and n12 are each independently 1 or 2,

n13 is 0 or 1,

the sum of n11, n12, and n13 is 3,

L₂₁, L₂₂, and L₂₃are different from one another,

n21 and n22 are each independently 1 or 2,

n23 is 0 or 1,

the sum of n21, n22, and n23 is 3, and

L₁₁and L₂₁are different from each other.

According to another aspect, provided is a layer including the composition described herein.

According to another aspect, provided is a light-emitting device including a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes the composition described herein.

In one or more embodiments, the emission layer of the light-emitting device may include the composition described herein.

According to another aspect, provided is an electronic apparatus including the light-emitting device described herein.

BRIEF DESCRIPTION OF THE DRAWING

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

The FIGURE shows a schematic cross-sectional view of a light-emitting device according to aspects of one or more embodiments.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. 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.

The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and/or.” 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.

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 of the present embodiments.

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.

It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with 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.

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 general inventive concept 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.

“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%, 5% of the stated value.

A composition according to one or more embodiments includes a first compound represented by Formula 1 and a second compound represented by Formula 2:

Ir(L₁₁)_n11(L₁₂)_n12(L₁₃)_n13 Formula 1

Ir(L₂₁)_n21(L₂₂)_n22(L₂₃)_n23 Formula 2

wherein each of Formulae 1 and 2 includes one iridium (Ir).

Each of the first compound and the second compound may be electrically neutral.

In Formulae 1 and 2, L₁₁, L₁₂, L₁₃, L₂₁, L₂₂, and L₂₃are each independently:

i) a bidentate ligand bonded to iridium (Ir) of Formula 1 via two nitrogen atoms, or a bidentate ligand bonded to iridium of Formula 2 via two nitrogen atoms,

ii) a bidentate ligand bonded to iridium of Formula 1 via a nitrogen atom and a carbon atom, or a bidentate ligand bonded to iridium of Formula 2 via a nitrogen atom and a carbon atom, or

iii) a bidentate ligand bonded to iridium of Formula 1 via two carbon atoms, or a bidentate ligand bonded to iridium of Formula 2 via two carbon atoms.

In one or more embodiments, in Formulae 1 and 2, L₁₁, L₁₂, L₁₃, L₂₁, L₂₂, and L₂₃may each be a bidentate ligand bonded to iridium in Formula 1 or 2 via a nitrogen atom and a carbon atom.

L₁₁, L₁₂, and L₁₃in Formula 1 are different from one another.

In Formula 1, n11 and n12 are each independently 1 or 2, and n13 is 0 or 1. The sum of n11, n12, and n13 is 3.

In one or more embodiments, in Formula 1, i) n11 may be 1, n12 may be 2, and n13 may be 0; or ii) n11 may be 2, n12 may be 1, and n13 may be 0.

L₂₁, L₂₂, and L₂₃in Formula 2 are different from one another.

In Formula 2, n21 and n22 re each independently 1 or 2, and n23 is 0 or 1. The sum of n21, n22, and n23 is 3.

In one or more embodiments, in Formula 2, i) n21 may be 1, n22 may be 2, and n23 may be 0; or ii) n21 may be 2, n22 may be 1, and n23 may be 0.

Each of the first compound and the second compound may be a heteroleptic complex.

In one or more embodiments, n13 in Formula 1 may be 0, and n23 in Formula 2 may be 0.

In Formulae 1 and 2,

L₁₁may be a ligand represented by Formula 1-1,

L₁₂may be a ligand represented by Formula 1-2,

L₁₃may be a ligand represented by Formula 1-1 or a ligand represented by Formula 1-2,

L₂₁may be a ligand represented by Formula 2-1,

L₂₂may be a ligand represented by Formula 2-2, and

L₂₃may be a ligand represented by Formula 2-1 or a ligand represented by Formula 2-2:

[Image Omitted]

wherein Y₁to Y₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be N or C.

In one or more embodiments, Y₁, Y₃, Y₅, and Y₇may be N, and Y₂, Y₄, Y₆, and Y₈may be C.

In one or more embodiments, i) Y₁and Y₂may each be C, ii) Y₃and Y₄may each be C, iii) Y₅and Y₆may each be C, or iv) Y₇and Y₈may each be C.

In Formulae 1, 2, 1-1, 1-2, 2-1, and 2-2, i) a bond between Y₁and iridium, a bond between Y₃and iridium, a bond between Y₅and iridium, and a bond between Y₇and iridium may each be a coordinate bond, and ii) a bond between Y₂and iridium, a bond between Y₄and iridium, a bond between Y₆and iridium, and a bond between Y₈and iridium may each be a covalent bond. Thus, each of the first compound and the second compound may be electrically neutral.

In Formulae 1-1, 1-2, 2-1, and 2-2, ring A₁, ring A₂, ring A₃, ring A₄, ring A₅, ring A₆, ring A₇, and ring A₈may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group.

In one or more embodiments, i) ring A₁, ring A₃, ring A₅, and ring A₇may each be a C₁-C₃₀heterocyclic group, and ii) ring A₂, ring A₄, ring A₆, and ring A₈may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group.

In one or more embodiments, i) ring A₁, ring A₃, ring A₅, and ring A₇may each be a C₁-C₃₀heterocyclic group, ii) ring A₂, ring A₄, ring A₆, and ring A₈may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group, iii) Y₁, Y₃, Y₅, and Y₇may each be N, and iv) Y₂, Y₄, Y₆, and Y₈may each be C.

In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A₁, ring A₃, ring A₅, and ring A₇may each independently be i) ring T1, ii) a condensed ring in which two or more ring T1 are condensed with each other, or iii) a condensed ring in which at least one ring T1 and at least one ring T2 are condensed with each other,

ring T1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and

ring T2 may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, or a benzene group.

In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A₂, ring A₄, ring A₆, and ring A₈may each be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other, the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and

the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A₁, ring A₃, ring A₅, and ring A₇may each independently be an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene 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 benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinooxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinooxadiazole group, a pyridinothiadiazole group, a pyrimidino pyrrole group, a pyrimidino pyrazole group, a pyrimidino imidazole group, a pyrimidino oxazole group, a pyrimidino isoxazole group, a pyrimidino thiazole group, a pyrimidino isothiazole group, a pyrimidino oxadiazole group, a pyrimidinothiadiazole group, a naphthopyrrole group, a naphthopyrazole group, a naphthoimidazole group, a naphthooxazole group, a naphthoisoxazole group, a naphthothiazole group, a naphthoisothiazole group, a naphthooxadiazole group, a naphthothiadiazole group, a phenanthrenopyrrole group, a phenanthrenopyrazole group, a phenanthrenoimidazole group, a phenanthrenooxazole group, a phenanthrenoisoxazole group, a phenanthrenothiazole group, a phenanthrenoisothiazole group, a phenanthrenooxadiazole group, a phenanthrenothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.

In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A₂, ring A₄, ring A₆, and ring A₈may each independently 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, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indolophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene 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 benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinooxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinooxadiazole group, a pyridinothiadiazole group, a pyrimidinopyrrole group, a pyrimidinopyrazole group, a pyrimidinoimidazole group, a pyrimidinooxazole group, a pyrimidinoisoxazole group, a pyrimidinothiazole group, a pyrimidinoisothiazole group, a pyrimidinooxadiazole group, a pyrimidinothiadiazole group, a naphthopyrrole group, a naphthopyrazole group, a naphthoimidazole group, a naphthooxazole group, a naphthoisoxazole group, a naphthothiazole group, a naphthoisothiazole group, a naphthooxadiazole group, a naphthothiadiazole group, a phenanthrenopyrrole group, a phenanthrenopyrazole group, a phenanthrenoimidazole group, a phenanthrenooxazole group, a phenanthrenoisoxazole group, a phenanthrenothiazole group, a phenanthrenoisothiazole group, a phenanthrenooxadiazole group, a phenanthrenothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with a cyclohexane group, a benzene group condensed with a norbornane group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.

Ring A₁and ring A₃in Formulae 1-1 and 1-2 may be different from each other.

In one or more embodiments, a Y₁-containing monocyclic group in ring A₁, a Y₂-containing monocyclic group in ring A₂, and a Y₄-containing monocyclic group in ring A₄may each be a 6-membered ring. In other words, ring A₁, ring A₂, and ring A₄may each comprise a 6-membered ring. For example, ring A₁and ring A₂may each be a 6-membered ring, and ring A₄may comprise a 6-membered ring.

In one or more embodiments, a Y₃-containing monocyclic group in ring A₃may be a 6-membered ring. In other words, ring A₃may comprise a 6-membered ring.

In one or more embodiments, a Y₃-containing monocyclic group in ring A₃may be a 5-membered ring. In other words, ring A₃may comprise a 5-membered ring.

In one or more embodiments, a Y₁-containing monocyclic group in ring A₁may be a 6-membered ring, and a Y₃-containing monocyclic group in ring A₃may be a 5-membered ring. In other words, ring A₁may comprise a 6-membered ring and ring A₃may comprise a 5-membered ring. For example, ring A₁may be a 6-membered ring and ring A₃may comprise a 5-membered ring.

Ring A₅and ring A₇in Formulae 2-1 and 2-2 may be identical to each other.

In one or more embodiments, a Y₅-containing monocyclic group in ring A₅, a Y₆-containing monocyclic group in ring A₆, and a Y₈-containing monocyclic group in ring A₈may each be a 6-membered ring. In other words, ring A₅, ring A₆, and ring A₈may each comprise a 6-membered ring. For example, ring A₅and ring A₆may each be a 6-membered ring, and ring A₈may comprise a 6-membered ring.

In one or more embodiments, a Y₇-containing monocyclic group in ring A₇may be a 6-membered ring. In other words, ring A₇may comprise a 6-membered ring. For example, ring A₇may be a 6-membered ring.

In one or more embodiments, a Y₇-containing monocyclic group in ring A₇may be a 5-membered ring. In other words, ring A₇may comprise a 5-membered ring. For example, ring A₇may be a 5-membered ring.

In one or more embodiments, a Y₅-containing monocyclic group in ring A₅and a Y₇-containing monocyclic group in ring A₇may each be a 6-membered ring.

In one or more embodiments, ring A₁, ring A₃, ring A₅, and ring A₇in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be i) an A group, ii) a polycyclic group in which two or more A groups are condensed with each other, or iii) a polycyclic group in which at least one A group and at least one B group are condensed with each other,

the A group may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and

the B group may be a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, or a silole group.

In one or more embodiments, in Formulae 1-2 and 2-2, ring A₃and ring A₇may each independently be i) a C group, ii) a polycyclic group in which two or more C groups are condensed with each other, or iii) a polycyclic group in which at least one C group and at least one D group are condensed with each other,

the C group may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, or an isothiazole group, and

the D group may be a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a furan group, a thiophene group, a selenophene group, a cyclopentadiene group, a silole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group.

In one or more embodiments, ring A₁and ring A₅in Formulae 1-1 and 2-1 may each independently be:

a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group; or

a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof.

In one or more embodiments, ring A₃and ring A₇in Formulae 1-2 and 2-2 may each independently be:

a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group;

a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof; or

an imidazole group, a benzimidazole group, a naphthoimidazole group, a phenanthrenoimidazole group, a pyridinooimidazole group, an oxazole group, a benzoxazole group, a naphthooxazole group, a phenanthrenooxazole group, a pyridinoooxazole group, a thiazole group, a benzothiazole group, a naphthothiazole group, a phenanthrenothiazole group, or a pyridinoothiazole group.

In one or more embodiments, ring A₂and ring A₄in Formulae 1-1 and 1-2 may be different from each other.

In one or more embodiments, ring A₆and ring A₈in Formulae 2-1 and 2-2 may be different from each other.

In one or more embodiments, ring A₂, ring A₄, ring A₆, and ring A₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be i) an E group, ii) a polycyclic group in which two or more E groups are condensed with each other, or iii) a polycyclic group in which at least one E group and at least one F group are condensed with each other,

the E group may be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and

the F group may be a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, an isoxazole group, or an isothiazole group.

In one or more embodiments, ring A₂in Formula 1-1 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.

In one or more embodiments, ring A₄in Formula 1-2 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.

In one or more embodiments, ring A₆in Formula 2-1 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.

In one or more embodiments, ring A₈in Formula 2-2 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.

In one or more embodiments, ring A₂and ring A₆in Formulae 1-1 and 2-1 may each independently be:

a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group; or

a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof.

In one or more embodiments, ring A₄and ring A₈in Formulae 1-2 and 2-2 may each independently be:

a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group or a phenanthrobenzofuran group; or

a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group, each condensed with at least one of a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a cyclohexane group, a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, an isoxazole group, an isothiazole group, or a combination thereof.

W₁to W₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be a single bond, a C₁-C₂₀alkylene group that is unsubstituted or substituted with at least one R_10a, a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

For example, W₁to W₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:

a single bond; or

a C₁-C₂₀alkylene group, a cyclopentene 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 cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran 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 pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole 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, a benzothiadiazole 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, each unsubstituted or substituted with at least one R_10a.

In one or more embodiments, W₁to W₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:

a single bond; or

a benzene group, a naphthalene group, a pyridine group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R_10a.

In one or more embodiments, W₁to W₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:

a single bond; or

a C₁-C₂₀alkylene group, a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a deuterated C₃-C₁₀cycloalkyl group, a fluorinated C₃-C₁₀cycloalkyl group, a (C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C₁-C₂₀alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.

Z₁to Z₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, 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 C₁-C₆₀alkylthio 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 C₇-C₆₀aryl alkyl 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 C₂-C₆₀heteroaryl alkyl 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), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q), or —P(Q₈)(Q). Q₁to Q₉are respectively as described herein.

In one or more embodiments, Z₁to Z₈in Formulae 1-1, 1-2, 2-1, and 2-2 may 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 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-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 a 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 benzoimidazolyl 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 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-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio 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 deuterated phenyl group, a fluorinated 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 benzoimidazolyl 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 a combination thereof; or

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), or —P(Q₈)(Q₉),

wherein Q₁to Q₉may 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 at least one of deuterium, —F, a C₁-C₁₀alkyl group, a phenyl group, or a combination thereof.

In one or more embodiments, Z₁to Z₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:

hydrogen, deuterium, —F, or a cyano group;

a C₁-C₂₀alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C₃-C₁₀cycloalkyl group, a deuterated C₃-C₁₀cycloalkyl group, a fluorinated C₃-C₁₀cycloalkyl group, a (C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a deuterated C₁-C₁₀heterocycloalkyl group, a fluorinated C₁-C₁₀heterocycloalkyl group, a (C₁-C₂₀alkyl)C₁-C₁₀heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C₁-C₂₀alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C₁-C₂₀alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C₁-C₂₀alkyl)dibenzothiophenyl group, or a combination thereof;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀a heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a deuterated C₁-C₂₀alkoxy group, a fluorinated C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a C₃-C₁₀cycloalkyl group, a deuterated C₃-C₁₀cycloalkyl group, a fluorinated C₃-C₁₀cycloalkyl group, a (C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a deuterated C₁-C₁₀heterocycloalkyl group, a fluorinated C₁-C₁₀heterocycloalkyl group, a (C₁-C₂₀alkyl)C₁-C₁₀heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C₁-C₂₀alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C₁-C₂₀alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C₁-C₂₀alkyl)dibenzothiophenyl group, or a combination thereof; or

—Si(Q₃)(Q₄)(Q₅) or —Ge(Q₃)(Q₄)(Q₅).

In one or more embodiments, in Formula 1-1,

e1 and d1 may each not be 0, and

one or more Z₁(s) may each independently be:

a C₁-C₂₀alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a phenyl group, or a combination thereof;

—Si(Q₃)(Q₄)(Q₅); or

—Ge(Q₃)(Q₄)(Q₅).

Q₃to Q₅are respectively as described herein.

In one or more embodiments, in Formula 2-1,

e5 and d5 may each not be 0, and

one or more Z₅(s) may each independently be:

a C₁-C₂₀alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a phenyl group, or a combination thereof;

—Si(Q₃)(Q₄)(Q₅); or

—Ge(Q₃)(Q₄)(Q₅).

Q₃to Q₅are respectively as described herein.

In one or more embodiments, Q₃to Q₅may each independently be:

a C₁-C₆₀alkyl group unsubstituted or substituted with at least one of deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof; or

a C₆-C₆₀aryl group unsubstituted or substituted with at least one of deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof.

In one or more embodiments, Q₃to Q₅may each independently be:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH₂; 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 at least one of deuterium, a C₁-C₁₀alkyl group, a phenyl group, or a combination thereof.

In one or more embodiments, Q₃to Q₅may be identical to each other (i.e., the same).

In one or more embodiments, two or more of Q₃to Q₅may be different from each other.

In one or more embodiments, Z₁to Z₈in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be: hydrogen, deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₁-C₁₀alkenyl group, a C₁-C₁₀alkoxy group, a C₁-C₁₀alkylthio group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-227, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-129, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F, —Si(Q₃)(Q₄)(Q₅), or —Ge(Q₃)(Q₄)(Q₅), wherein Q₃to Q₅are respectively as described herein:

[Image Omitted]

[Image Omitted]

In Formulae 9-1 to 9-39, 9-201 to 9-227, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:

[Image Omitted]

wherein * indicates a binding site to a neighboring atom

The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 9-701 to 9-710:

[Image Omitted]

wherein * indicates a binding site to a neighboring atom

The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:

[Image Omitted]

wherein * indicates a binding site to a neighboring atom

The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-617:

[Image Omitted]

wherein * indicates a binding site to a neighboring atom.

e1 to e8 and d1 to d8 in Formulae 1-1, 1-2, 2-1, and 2-2 indicates numbers of Z₁to Z₈group(s), a group represented by *—[W₁—(Z₁)_e1], a group represented by *—[W₂—(Z₂)_e2], a group represented by *—[W₃—(Z₃)_e3], a group represented by *—[W₄—(Z₄)_e4], a group represented by *—[W₅—(Z₅)_e5], a group represented by *—[W₆—(Z₆)_e6], a group represented by *—[W₇—(Z₇)_e7], and a group represented by *—[W₈—(Z₈)_e8], respectively, and may each independently be an integer from 0 to 20. When e1 is 2 or more, two or more of Z₁(s) may be identical to or different from each other, when e2 is 2 or more, two or more of Z₂(s) may be identical to or different from each other, when e3 is 2 or more, two or more of Z₃(s) may be identical to or different from each other, when e4 is 2 or more, two or more of Z₄(s) may be identical to or different from each other, when e5 is 2 or more, two or more of Z₅(s) may be identical to or different from each other, when e6 is 2 or more, two or more of Z₆(s) may be identical to or different from each other, when e7 is 2 or more, two or more of Z₇(s) may be identical to or different from each other, when e8 is 2 or more, two or more of Z₈(s) may be identical to or different from each other, when d1 is 2 or more, two or more of groups represented by *—[W₁—(Z₁)_e1] may be identical to or different from each other, when d2 is 2 or more, two or more of groups represented by *—[W₂—(Z₂)_e2] may be identical to or different from each other, when d3 is 2 or more, two or more of groups represented by *—[W₃—(Z₃)_e3] may be identical to or different from each other, when d4 is 2 or more, two or more of groups represented by *—[W₄—(Z₄)_e1] may be identical to or different from each other, when d5 is 2 or more, two or more of groups represented by *—[W₅—(Z₅)_e5] may be identical to or different from each other, when d6 is 2 or more, two or more of groups represented by *—[W₆—(Z₆)_e6] may be identical to or different from each other, when d7 is 2 or more, two or more of groups represented by *—[W₇—(Z₇)_e7] may be identical to or different from each other, and when d8 is 2 or more, two or more of groups represented by *—[W₈—(Z₈)_e8] may be identical to or different from each other. In one or more embodiments, e1 to e8 and d1 to d8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be 0, 1, 2, or 3.

* and *′ herein each indicate a binding site to a neighboring atom, unless otherwise stated.

In Formulae 1-1, 1-2, 2-1, and 2-2, one or more of i) two or more of a plurality of Z₁(s), ii) two or more of a plurality of Z₂(s), iii) two or more of a plurality of Z₃(s), iv) two or more of a plurality of Z₄(s), v) two or more of a plurality of Z₅(s), vi) two or more of a plurality of Z₆(s), vii) two or more of a plurality of Z₇(s), and viii) two or more of a plurality of Z₈(s) may respectively optionally be bonded to each other to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

R_10amay be as described in connection with Z₁herein.

* and *′ in Formulae 1-1, 1-2, 2-1, and 2-2 each indicate a binding site to iridium in Formulae 1 and 2.

In one or more embodiments, a group represented by

[Image Omitted]

in Formula 1-1 may be a group represented by one of Formulae A1-1 to A1-3.

In one or more embodiments, a group represented by

[Image Omitted]

in Formula 2-1 may be a group represented by one of Formulae A5-1 to A5-3:

[Image Omitted]

In Formulae A1-1 to A1-3 and A5-1 to A5-3,

Z₁₁to Z₁₄are respectively as described in connection with Z₁herein,

Z₅₁to Z₅₄are respectively as described in connection with Z₅herein,

R_10ais as described herein,

a14 may be an integer from 0 to 4,

a18 may be an integer from 0 to 8,

*′ indicates a binding site to iridium in Formulae 1 and 2, and

*″ indicates a binding site to ring A₂or ring A₆.

In one or more embodiments, at least one of Z₁₁, Z₁₂, and Z₁₄(for example, Z₁₄) in Formulae A1-1 to A1-3 and at least one of Z₅₁, Z₅₂, and Z₅₄(for example, Z₅₄) in Formulae A5-1 to A5-3 may each independently be:

a C₁-C₂₀alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a phenyl group, or a combination thereof;

—Si(Q₃)(Q₄)(Q₅); or

—Ge(Q₃)(Q₄)(Q₅).

In one or more embodiments,

Y₃in Formula 1-2 and Y₇in Formula 2-2 may each be N, and

a group represented by

[Image Omitted]

in Formula 1-2, and

a group represented by

[Image Omitted]

in Formula 2-2 may each independently be a group represented by one of Formulae NR1 to NR48:

[Image Omitted]

wherein, in Formulae NR1 to NR48,

Y₃₉may be O, S, Se, N—[W₃—(Z₃)_e3], N—[W₇—(Z₇)_e7], C(Z_39a)(Z_39b), C(Z_79a)(Z_79b), Si(Z_39a)(Z_39b), or Si(Z_79a)(Z_79b),

W₃, W₇, Z₃, Z₇, e3, and e7 are respectively as described herein, Z_39aand Z_39bare respectively as described in connection with Z₃herein, and Z_79aand Z_79bare each as described in connection with Z₇herein,

*′ indicates a binding site to iridium in Formula 1 or 2, and

*″ indicates a binding site to ring A₄or ring A₈.

In one or more embodiments, a group represented by

[Image Omitted]

in Formula 1-2 may be a group represented by one of Formulae NR30 to NR48.

In one or more embodiments,

Y₂in Formula 1-1, Y₄in Formula 1-2, Y₆in Formula 2-1, and Y₈in Formula 2-2 may each be C, and

a group represented by

[Image Omitted]

in Formula 1-1,

a group represented by

[Image Omitted]

in Formula 1-2,

a group represented by

[Image Omitted]

in Formula 2-1, and

a group represented by

[Image Omitted]

in Formula 2-2 may each independently be a group represented by one of Formulae CR1 to CR29:

[Image Omitted]

wherein, in Formulae CR1 to CR29,

Y₄₉may be O, S, Se, N—[W₂—(Z₂)_e2], N—[W₄—(Z₄)_e4], N—[W₆—(Z₆)_e6], N—[W₈—(Z₈)_e8], C(Z_29a)(Z_29b), C(Z_49a)(Z_49b), C(Z_69a)(Z_69b), C(Z_89a)(Z_89b), Si(Z_29a)(Z_29b), Si(Z_49a)(Z_49b), Si(Z_69a)(Z_69b), or Si(Z_89a)(Z_89b),

W₂, W₄, W₆, W₈, Z₂, Z₄, Z₆, Z₈, e2, e4, e6, and e8 are respectively as described herein, Z_29aand Z_29bare respectively as described in connection with Z₂herein, Z₄₉a and Z_49bare respectively as described in connection with Z₄herein, Z_69aand Z_69bare respectively as described in connection with Z₆herein, and Z_89aand Z_89bare respectively as described in connection with Z₈herein,

Y₂₁to Y₂₄may each independently be N or C,

ring A₄₀may be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group (for example, a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, or benzoquinazoline group),

* indicates a binding site to iridium in Formulae 1 and 2, and

*″ indicates a binding site to ring A₁, ring A₃, ring A₅, and ring A₇.

In one or more embodiments, a group represented by

[Image Omitted]

in Formulae CR24 to CR29 may be a group represented by one of Formulae CR(1) to CR(13):

[Image Omitted]

wherein, in Formulae CR(1) to CR(13),

Y₄₉is as described herein, and

Y₃₁to Y₃₄and Y₄₁to Y₄₈may each independently be C or N.

In one or more embodiments, the first compound may include at least one deuterium.

In one or more embodiments, the second compound may include at least one deuterium.

The first compound may emit a first light including a first spectrum, and λP(1) may be an emission peak wavelength (in nanometers, nm) of the first spectrum.

The second compound may emit a second light including a second spectrum, and λP(2) may be an emission peak wavelength (nm) of the second spectrum.

The λP(1) and the λP(2) may be evaluated from a photoluminescence (PL) spectra measured for a first film and a second film, respectively.

As used herein, the “first film” is a film including the first compound, and the “second film” is a film including the second compound. The first film and the second film may be manufactured using various methods such as any method, for example, a vacuum deposition method, a coating and heating method. The first film and the second film may further include other compounds, for example, a host described herein, in addition to the first compound and the second compound.

In one or more embodiments, each of the λP(1) and the λP(2) may be about 480 nm to about 580 nm, or about 510 nm to about 570 nm.

In one or more embodiments, an absolute value of a difference between the λP(1) and the λP(2) may be about 0 nm to about 30 nm, about 0 nm to about 20 nm, or about 0 nm to about 10 nm.

In one or more embodiments, the first light and the second light may each be green light.

In one or more embodiments, the first light may be green light, and the second light may be yellow-green light.

In one or more embodiments, the first light and the second light may each be yellow-green light.

In one or more embodiments, the first light may be yellow-green light, and the second light may be yellow light.

In one or more embodiments, the first light and the second light may each be yellow light.

In one or more embodiments, L₁₁and L₁₃in Formula 1, L₂₁and L₂₃in Formula 2, a ligand represented by Formula 1-1, and a ligand represented by Formula 2-1 may each independently be represented by one of Formulae A1 to A380:

[Image Omitted]

[Image Omitted]

[Image Omitted]

In one or more embodiments, L₁₂and L₁₃in Formula 1, L₂₂and L₂₃in Formula 2, a ligand represented by Formula 1-2, and a ligand represented by Formula 2-2 may each independently be represented by one of B1 to B1542:

[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]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

[Image Omitted]

wherein * and *′ each indicate a binding site to iridium.

In one or more embodiments, L₁₂and L₁₃in Formula 1 and a ligand represented by Formula 1-2 may each independently be selected from B to B780.

In one or more embodiments, L₂₂and L₂₃in Formula 2 and a ligand represented by Formula 2-2 may each independently be selected from B781 to B1542.

In one or more embodiments, the first compound and the second compound may each be one of compounds described in Tables 1 to 11 below.

TABLE 1

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-1
Ax
B1

x-2
Ax
B2

x-3
Ax
B3

x-4
Ax
B4

x-5
Ax
B5

x-6
Ax
B6

x-7
Ax
B7

x-8
Ax
B8

x-9
Ax
B9

x-10
Ax
B10

x-11
Ax
B11

x-12
Ax
B12

x-13
Ax
B13

x-14
Ax
B14

x-15
Ax
B15

x-16
Ax
B16

x-17
Ax
B17

x-18
Ax
B18

x-19
Ax
B19

x-20
Ax
B20

x-21
Ax
B21

x-22
Ax
B22

x-23
Ax
B23

x-24
Ax
B24

x-25
Ax
B25

x-26
Ax
B26

x-27
Ax
B27

x-28
Ax
B28

x-29
Ax
B29

x-30
Ax
B30

x-31
Ax
B31

x-32
Ax
B32

x-33
Ax
B33

x-34
Ax
B34

x-35
Ax
B35

x-36
Ax
B36

x-37
Ax
B37

x-38
Ax
B38

x-39
Ax
B39

x-40
Ax
B40

x-41
Ax
B41

x-42
Ax
B42

x-43
Ax
B43

x-44
Ax
B44

x-45
Ax
B45

x-46
Ax
B46

x-47
Ax
B47

x-48
Ax
B48

x-49
Ax
B49

x-50
Ax
B50

x-51
Ax
B51

x-52
Ax
B52

x-53
Ax
B53

x-54
Ax
B54

x-55
Ax
B55

x-56
Ax
B56

x-57
Ax
B57

x-58
Ax
B58

x-59
Ax
B59

x-60
Ax
B60

x-61
Ax
B61

x-62
Ax
B62

x-63
Ax
B63

x-64
Ax
B64

x-65
Ax
B65

x-66
Ax
B66

x-67
Ax
B67

x-68
Ax
B68

x-69
Ax
B69

x-70
Ax
B70

x-71
Ax
B71

x-72
Ax
B72

x-73
Ax
B73

x-74
Ax
B74

x-75
Ax
B75

x-76
Ax
B76

x-77
Ax
B77

x-78
Ax
B78

x-79
Ax
B79

x-80
Ax
B80

x-81
Ax
B81

x-82
Ax
B82

x-83
Ax
B83

x-84
Ax
B84

x-85
Ax
B85

x-86
Ax
B86

x-87
Ax
B87

x-88
Ax
B88

x-89
Ax
B89

x-90
Ax
B90

x-91
Ax
B91

x-92
Ax
B92

x-93
Ax
B93

x-94
Ax
B94

x-95
Ax
B95

x-96
Ax
B96

x-97
Ax
B97

x-98
Ax
B98

x-99
Ax
B99

x-100
Ax
B100

x-101
Ax
B101

x-102
Ax
B102

x-103
Ax
B103

x-104
Ax
B104

x-105
Ax
B105

x-106
Ax
B106

x-107
Ax
B107

x-108
Ax
B108

x-109
Ax
B109

x-110
Ax
B110

x-111
Ax
B111

x-112
Ax
B112

x-113
Ax
B113

x-114
Ax
B114

x-115
Ax
B115

x-116
Ax
B116

x-117
Ax
B117

x-118
Ax
B118

x-119
Ax
B119

x-120
Ax
B120

x-121
Ax
B121

x-122
Ax
B122

x-123
Ax
B123

x-124
Ax
B124

x-125
Ax
B125

x-126
Ax
B126

x-127
Ax
B127

x-128
Ax
B128

x-129
Ax
B129

x-130
Ax
B130

x-131
Ax
B131

x-132
Ax
B132

x-133
Ax
B133

x-134
Ax
B134

x-135
Ax
B135

x-136
Ax
B136

x-137
Ax
B137

x-138
Ax
B138

x-139
Ax
B139

x-140
Ax
B140

x-141
Ax
B141

x-142
Ax
B142

x-143
Ax
B143

x-144
Ax
B144

x-145
Ax
B145

x-146
Ax
B146

x-147
Ax
B147

x-148
Ax
B148

x-149
Ax
B149

x-150
Ax
B150

TABLE 2

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-151
Ax
B151

x-152
Ax
B152

x-153
Ax
B153

x-154
Ax
B154

x-155
Ax
B155

x-156
Ax
B156

x-157
Ax
B157

x-158
Ax
B158

x-159
Ax
B159

x-160
Ax
B160

x-161
Ax
B161

x-162
Ax
B162

x-163
Ax
B163

x-164
Ax
B164

x-165
Ax
B165

x-166
Ax
B166

x-167
Ax
B167

x-168
Ax
B168

x-169
Ax
B169

x-170
Ax
B170

x-171
Ax
B171

x-172
Ax
B172

x-173
Ax
B173

x-174
Ax
B174

x-175
Ax
B175

x-176
Ax
B176

x-177
Ax
B177

x-178
Ax
B178

x-179
Ax
B179

x-180
Ax
B180

x-181
Ax
B181

x-182
Ax
B182

x-183
Ax
B183

x-184
Ax
B184

x-185
Ax
B185

x-186
Ax
B186

x-187
Ax
B187

x-188
Ax
B188

x-189
Ax
B189

x-190
Ax
B190

x-191
Ax
B191

x-192
Ax
B192

x-193
Ax
B193

x-194
Ax
B194

x-195
Ax
B195

x-196
Ax
B196

x-197
Ax
B197

x-198
Ax
B198

x-199
Ax
B199

x-200
Ax
B200

x-201
Ax
B201

x-202
Ax
B202

x-203
Ax
B203

x-204
Ax
B204

x-205
Ax
B205

x-206
Ax
B206

x-207
Ax
B207

x-208
Ax
B208

x-209
Ax
B209

x-210
Ax
B210

x-211
Ax
B211

x-212
Ax
B212

x-213
Ax
B213

x-214
Ax
B214

x-215
Ax
B215

x-216
Ax
B216

x-217
Ax
B217

x-218
Ax
B218

x-219
Ax
B219

x-220
Ax
B220

x-221
Ax
B221

x-222
Ax
B222

x-223
Ax
B223

x-224
Ax
B224

x-225
Ax
B225

x-226
Ax
B226

x-227
Ax
B227

x-228
Ax
B228

x-229
Ax
B229

x-230
Ax
B230

x-231
Ax
B231

x-232
Ax
B232

x-233
Ax
B233

x-234
Ax
B234

x-235
Ax
B235

x-236
Ax
B236

x-237
Ax
B237

x-238
Ax
B238

x-239
Ax
B239

x-240
Ax
B240

x-241
Ax
B241

x-242
Ax
B242

x-243
Ax
B243

x-244
Ax
B244

x-245
Ax
B245

x-246
Ax
B246

x-247
Ax
B247

x-248
Ax
B248

x-249
Ax
B249

x-250
Ax
B250

x-251
Ax
B251

x-252
Ax
B252

x-253
Ax
B253

x-254
Ax
B254

x-255
Ax
B255

x-256
Ax
B256

x-257
Ax
B257

x-258
Ax
B258

x-259
Ax
B259

x-260
Ax
B260

x-261
Ax
B261

x-262
Ax
B262

x-263
Ax
B263

x-264
Ax
B264

x-265
Ax
B265

x-266
Ax
B266

x-267
Ax
B267

x-268
Ax
B268

x-269
Ax
B269

x-270
Ax
B270

x-271
Ax
B271

x-272
Ax
B272

x-273
Ax
B273

x-274
Ax
B274

x-275
Ax
B275

x-276
Ax
B276

x-277
Ax
B277

x-278
Ax
B278

x-279
Ax
B279

x-280
Ax
B280

x-281
Ax
B281

x-282
Ax
B282

x-283
Ax
B283

x-284
Ax
B284

x-285
Ax
B285

x-286
Ax
B286

x-287
Ax
B287

x-288
Ax
B288

x-289
Ax
B289

x-290
Ax
B290

x-291
Ax
B291

x-292
Ax
B292

x-293
Ax
B293

x-294
Ax
B294

x-295
Ax
B295

x-296
Ax
B296

x-297
Ax
B297

x-298
Ax
B298

x-299
Ax
B299

x-300
Ax
B300

TABLE 3

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-301
Ax
B301

x-302
Ax
B302

x-303
Ax
B303

x-304
Ax
B304

x-305
Ax
B305

x-306
Ax
B306

x-307
Ax
B307

x-308
Ax
B308

x-309
Ax
B309

x-310
Ax
B310

x-311
Ax
B311

x-312
Ax
B312

x-313
Ax
B313

x-314
Ax
B314

x-315
Ax
B315

x-316
Ax
B316

x-317
Ax
B317

x-318
Ax
B318

x-319
Ax
B319

x-320
Ax
B320

x-321
Ax
B321

x-322
Ax
B322

x-323
Ax
B323

x-324
Ax
B324

x-325
Ax
B325

x-326
Ax
B326

x-327
Ax
B327

x-328
Ax
B328

x-329
Ax
B329

x-330
Ax
B330

x-331
Ax
B331

x-332
Ax
B332

x-333
Ax
B333

x-334
Ax
B334

x-335
Ax
B335

x-336
Ax
B336

x-337
Ax
B337

x-338
Ax
B338

x-339
Ax
B339

x-340
Ax
B340

x-341
Ax
B341

x-342
Ax
B342

x-343
Ax
B343

x-344
Ax
B344

x-345
Ax
B345

x-346
Ax
B346

x-347
Ax
B347

x-348
Ax
B348

x-349
Ax
B349

x-350
Ax
B350

x-351
Ax
B351

x-352
Ax
B352

x-353
Ax
B353

x-354
Ax
B354

x-355
Ax
B355

x-356
Ax
B356

x-357
Ax
B357

x-358
Ax
B358

x-359
Ax
B359

x-360
Ax
B360

x-361
Ax
B361

x-362
Ax
B362

x-363
Ax
B363

x-364
Ax
B364

x-365
Ax
B365

x-366
Ax
B366

x-367
Ax
B367

x-368
Ax
B368

x-369
Ax
B369

x-370
Ax
B370

x-371
Ax
B371

x-372
Ax
B372

x-373
Ax
B373

x-374
Ax
B374

x-375
Ax
B375

x-376
Ax
B376

x-377
Ax
B377

x-378
Ax
B378

x-379
Ax
B379

x-380
Ax
B380

x-381
Ax
B381

x-382
Ax
B382

x-383
Ax
B383

x-384
Ax
B384

x-385
Ax
B385

x-386
Ax
B386

x-387
Ax
B387

x-388
Ax
B388

x-389
Ax
B389

x-390
Ax
B390

x-391
Ax
B391

x-392
Ax
B392

x-393
Ax
B393

x-394
Ax
B394

x-395
Ax
B395

x-396
Ax
B396

x-397
Ax
B397

x-398
Ax
B398

x-399
Ax
B399

x-400
Ax
B400

x-401
Ax
B401

x-402
Ax
B402

x-403
Ax
B403

x-404
Ax
B404

x-405
Ax
B405

x-406
Ax
B406

x-407
Ax
B407

x-408
Ax
B408

x-409
Ax
B409

x-410
Ax
B410

x-411
Ax
B411

x-412
Ax
B412

x-413
Ax
B413

x-414
Ax
B414

x-415
Ax
B415

x-416
Ax
B416

x-417
Ax
B417

x-418
Ax
B418

x-419
Ax
B419

x-420
Ax
B420

x-421
Ax
B421

x-422
Ax
B422

x-423
Ax
B423

x-424
Ax
B424

x-425
Ax
B425

x-426
Ax
B426

x-427
Ax
B427

x-428
Ax
B428

x-429
Ax
B429

x-430
Ax
B430

x-431
Ax
B431

x-432
Ax
B432

x-433
Ax
B433

x-434
Ax
B434

x-435
Ax
B435

x-436
Ax
B436

x-437
Ax
B437

x-438
Ax
B438

x-439
Ax
B439

x-440
Ax
B440

x-441
Ax
B441

x-442
Ax
B442

x-443
Ax
B443

x-444
Ax
B444

x-445
Ax
B445

x-446
Ax
B446

x-447
Ax
B447

x-448
Ax
B448

x-449
Ax
B449

x-450
Ax
B450

TABLE 4

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-451
Ax
B451

x-452
Ax
B452

x-453
Ax
B453

x-454
Ax
B454

x-455
Ax
B455

x-456
Ax
B456

x-457
Ax
B457

x-458
Ax
B458

x-459
Ax
B459

x-460
Ax
B460

x-461
Ax
B461

x-462
Ax
B462

x-463
Ax
B463

x-464
Ax
B464

x-465
Ax
B465

x-466
Ax
B466

x-467
Ax
B467

x-468
Ax
B468

x-469
Ax
B469

x-470
Ax
B470

x-471
Ax
B471

x-472
Ax
B472

x-473
Ax
B473

x-474
Ax
B474

x-475
Ax
B475

x-476
Ax
B476

x-477
Ax
B477

x-478
Ax
B478

x-479
Ax
B479

x-480
Ax
B480

x-481
Ax
B481

x-482
Ax
B482

x-483
Ax
B483

x-484
Ax
B484

x-485
Ax
B485

x-486
Ax
B486

x-487
Ax
B487

x-488
Ax
B488

x-489
Ax
B489

x-490
Ax
B490

x-491
Ax
B491

x-492
Ax
B492

x-493
Ax
B493

x-494
Ax
B494

x-495
Ax
B495

x-496
Ax
B496

x-497
Ax
B497

x-498
Ax
B498

x-499
Ax
B499

x-500
Ax
B500

x-501
Ax
B501

x-502
Ax
B502

x-503
Ax
B503

x-504
Ax
B504

x-505
Ax
B505

x-506
Ax
B506

x-507
Ax
B507

x-508
Ax
B508

x-509
Ax
B509

x-510
Ax
B510

x-511
Ax
B511

x-512
Ax
B512

x-513
Ax
B513

x-514
Ax
B514

x-515
Ax
B515

x-516
Ax
B516

x-517
Ax
B517

x-518
Ax
B518

x-519
Ax
B519

x-520
Ax
B520

x-521
Ax
B521

x-522
Ax
B522

x-523
Ax
B523

x-524
Ax
B524

x-525
Ax
B525

x-526
Ax
B526

x-527
Ax
B527

x-528
Ax
B528

x-529
Ax
B529

x-530
Ax
B530

x-531
Ax
B531

x-532
Ax
B532

x-533
Ax
B533

x-534
Ax
B534

x-535
Ax
B535

x-536
Ax
B536

x-537
Ax
B537

x-538
Ax
B538

x-539
Ax
B539

x-540
Ax
B540

x-541
Ax
B541

x-542
Ax
B542

x-543
Ax
B543

x-544
Ax
B544

x-545
Ax
B545

x-546
Ax
B546

x-547
Ax
B547

x-548
Ax
B548

x-549
Ax
B549

x-550
Ax
B550

x-551
Ax
B551

x-552
Ax
B552

x-553
Ax
B553

x-554
Ax
B554

x-555
Ax
B555

x-556
Ax
B556

x-557
Ax
B557

x-558
Ax
B558

x-559
Ax
B559

x-560
Ax
B560

x-561
Ax
B561

x-562
Ax
B562

x-563
Ax
B563

x-564
Ax
B564

x-565
Ax
B565

x-566
Ax
B566

x-567
Ax
B567

x-568
Ax
B568

x-569
Ax
B569

x-570
Ax
B570

x-571
Ax
B571

x-572
Ax
B572

x-573
Ax
B573

x-574
Ax
B574

x-575
Ax
B575

x-576
Ax
B576

x-577
Ax
B577

x-578
Ax
B578

x-579
Ax
B579

x-580
Ax
B580

x-581
Ax
B581

x-582
Ax
B582

x-583
Ax
B583

x-584
Ax
B584

x-585
Ax
B585

x-586
Ax
B586

x-587
Ax
B587

x-588
Ax
B588

x-589
Ax
B589

x-590
Ax
B590

x-591
Ax
B591

x-592
Ax
B592

x-593
Ax
B593

x-594
Ax
B594

x-595
Ax
B595

x-596
Ax
B596

x-597
Ax
B597

x-598
Ax
B598

x-599
Ax
B599

x-600
Ax
B600

TABLE 5

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-601
Ax
B601

x-602
Ax
B602

x-603
Ax
B603

x-604
Ax
B604

x-605
Ax
B605

x-606
Ax
B606

x-607
Ax
B607

x-608
Ax
B608

x-609
Ax
B609

x-610
Ax
B610

x-611
Ax
B611

x-612
Ax
B612

x-613
Ax
B613

x-614
Ax
B614

x-615
Ax
B615

x-616
Ax
B616

x-617
Ax
B617

x-618
Ax
B618

x-619
Ax
B619

x-620
Ax
B620

x-621
Ax
B621

x-622
Ax
B622

x-623
Ax
B623

x-624
Ax
B624

x-625
Ax
B625

x-626
Ax
B626

x-627
Ax
B627

x-628
Ax
B628

x-629
Ax
B629

x-630
Ax
B630

x-631
Ax
B631

x-632
Ax
B632

x-633
Ax
B633

x-634
Ax
B634

x-635
Ax
B635

x-636
Ax
B636

x-637
Ax
B637

x-638
Ax
B638

x-639
Ax
B639

x-640
Ax
B640

x-641
Ax
B641

x-642
Ax
B642

x-643
Ax
B643

x-644
Ax
B644

x-645
Ax
B645

x-646
Ax
B646

x-647
Ax
B647

x-648
Ax
B648

x-649
Ax
B649

x-650
Ax
B650

x-651
Ax
B651

x-652
Ax
B652

x-653
Ax
B653

x-654
Ax
B654

x-655
Ax
B655

x-656
Ax
B656

x-657
Ax
B657

x-658
Ax
B658

x-659
Ax
B659

x-660
Ax
B660

x-661
Ax
B661

x-662
Ax
B662

x-663
Ax
B663

x-664
Ax
B664

x-665
Ax
B665

x-666
Ax
B666

x-667
Ax
B667

x-668
Ax
B668

x-669
Ax
B669

x-670
Ax
B670

x-671
Ax
B671

x-672
Ax
B672

x-673
Ax
B673

x-674
Ax
B674

x-675
Ax
B675

x-676
Ax
B676

x-677
Ax
B677

x-678
Ax
B678

x-679
Ax
B679

x-680
Ax
B680

x-681
Ax
B681

x-682
Ax
B682

x-683
Ax
B683

x-684
Ax
B684

x-685
Ax
B685

x-686
Ax
B686

x-687
Ax
B687

x-688
Ax
B688

x-689
Ax
B689

x-690
Ax
B690

x-691
Ax
B691

x-692
Ax
B692

x-693
Ax
B693

x-694
Ax
B694

x-695
Ax
B695

x-696
Ax
B696

x-697
Ax
B697

x-698
Ax
B698

x-699
Ax
B699

x-700
Ax
B700

x-701
Ax
B701

x-702
Ax
B702

x-703
Ax
B703

x-704
Ax
B704

x-705
Ax
B705

x-706
Ax
B706

x-707
Ax
B707

x-708
Ax
B708

x-709
Ax
B709

x-710
Ax
B710

x-711
Ax
B711

x-712
Ax
B712

x-713
Ax
B713

x-714
Ax
B714

x-715
Ax
B715

x-716
Ax
B716

x-717
Ax
B717

x-718
Ax
B718

x-719
Ax
B719

x-720
Ax
B720

x-721
Ax
B721

x-722
Ax
B722

x-723
Ax
B723

x-724
Ax
B724

x-725
Ax
B725

x-726
Ax
B726

x-727
Ax
B727

x-728
Ax
B728

x-729
Ax
B729

x-730
Ax
B730

x-731
Ax
B731

x-732
Ax
B732

x-733
Ax
B733

x-734
Ax
B734

x-735
Ax
B735

x-736
Ax
B736

x-737
Ax
B737

x-738
Ax
B738

x-739
Ax
B739

x-740
Ax
B740

x-741
Ax
B741

x-742
Ax
B742

x-743
Ax
B743

x-744
Ax
B744

x-745
Ax
B745

x-746
Ax
B746

x-747
Ax
B747

x-748
Ax
B748

x-749
Ax
B749

x-750
Ax
B750

TABLE 6

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-751
Ax
B751

x-752
Ax
B752

x-753
Ax
B753

x-754
Ax
B754

x-755
Ax
B755

x-756
Ax
B756

x-757
Ax
B757

x-758
Ax
B758

x-759
Ax
B759

x-760
Ax
B760

x-761
Ax
B761

x-762
Ax
B762

x-763
Ax
B763

x-764
Ax
B764

x-765
Ax
B765

x-766
Ax
B766

x-767
Ax
B767

x-768
Ax
B768

x-769
Ax
B769

x-770
Ax
B770

x-771
Ax
B771

x-772
Ax
B772

x-773
Ax
B773

x-774
Ax
B774

x-775
Ax
B775

x-776
Ax
B776

x-777
Ax
B777

x-778
Ax
B778

x-779
Ax
B779

x-780
Ax
B780

x-781
Ax
B781

x-782
Ax
B782

x-783
Ax
B783

x-784
Ax
B784

x-785
Ax
B785

x-786
Ax
B786

x-787
Ax
B787

x-788
Ax
B788

x-789
Ax
B789

x-790
Ax
B790

x-791
Ax
B791

x-792
Ax
B792

x-793
Ax
B793

x-794
Ax
B794

x-795
Ax
B795

x-796
Ax
B796

x-797
Ax
B797

x-798
Ax
B798

x-799
Ax
B799

x-801
Ax
B801

x-802
Ax
B802

x-803
Ax
B803

x-804
Ax
B804

x-805
Ax
B805

x-806
Ax
B806

x-807
Ax
B807

x-808
Ax
B808

x-809
Ax
B809

x-810
Ax
B810

x-811
Ax
B811

x-812
Ax
B812

x-813
Ax
B813

x-814
Ax
B814

x-815
Ax
B815

x-816
Ax
B816

x-817
Ax
B817

x-818
Ax
B818

x-819
Ax
B819

x-820
Ax
B820

x-821
Ax
B821

x-822
Ax
B822

x-823
Ax
B823

x-824
Ax
B824

x-825
Ax
B825

x-826
Ax
B826

x-827
Ax
B827

x-828
Ax
B828

x-829
Ax
B829

x-830
Ax
B830

x-831
Ax
B831

x-832
Ax
B832

x-833
Ax
B833

x-834
Ax
B834

x-835
Ax
B835

x-836
Ax
B836

x-837
Ax
B837

x-838
Ax
B838

x-839
Ax
B839

x-840
Ax
B840

x-841
Ax
B841

x-842
Ax
B842

x-843
Ax
B843

x-844
Ax
B844

x-845
Ax
B845

x-846
Ax
B846

x-847
Ax
B847

x-848
Ax
B848

x-849
Ax
B849

x-850
Ax
B850

x-851
Ax
B851

x-852
Ax
B852

x-853
Ax
B853

x-854
Ax
B854

x-855
Ax
B855

x-856
Ax
B856

x-857
Ax
B857

x-858
Ax
B858

x-859
Ax
B859

x-860
Ax
B860

x-861
Ax
B861

x-862
Ax
B862

x-863
Ax
B863

x-864
Ax
B864

x-865
Ax
B865

x-866
Ax
B866

x-867
Ax
B867

x-868
Ax
B868

x-869
Ax
B869

x-870
Ax
B870

x-871
Ax
B871

x-872
Ax
B872

x-873
Ax
B873

x-874
Ax
B874

x-875
Ax
B875

x-876
Ax
B876

x-877
Ax
B877

x-878
Ax
B878

x-879
Ax
B879

x-880
Ax
B880

x-881
Ax
B881

x-882
Ax
B882

x-883
Ax
B883

x-884
Ax
B884

x-885
Ax
B885

x-886
Ax
B886

x-887
Ax
B887

x-888
Ax
B888

x-889
Ax
B889

x-890
Ax
B890

x-891
Ax
B891

x-892
Ax
B892

x-893
Ax
B893

x-894
Ax
B894

x-895
Ax
B895

x-896
Ax
B896

x-897
Ax
B897

x-898
Ax
B898

x-899
Ax
B899

x-900
Ax
B900

TABLE 7

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-901
Ax
B901

x-902
Ax
B902

x-903
Ax
B903

x-904
Ax
B904

x-905
Ax
B905

x-906
Ax
B906

x-907
Ax
B907

x-908
Ax
B908

x-909
Ax
B909

x-910
Ax
B910

x-911
Ax
B911

x-912
Ax
B912

x-913
Ax
B913

x-914
Ax
B914

x-915
Ax
B915

x-916
Ax
B916

x-917
Ax
B917

x-918
Ax
B918

x-919
Ax
B919

x-920
Ax
B920

x-921
Ax
B921

x-922
Ax
B922

x-923
Ax
B923

x-924
Ax
B924

x-925
Ax
B925

x-926
Ax
B926

x-927
Ax
B927

x-928
Ax
B928

x-929
Ax
B929

x-930
Ax
B930

x-931
Ax
B931

x-932
Ax
B932

x-933
Ax
B933

x-934
Ax
B934

x-935
Ax
B935

x-936
Ax
B936

x-937
Ax
B937

x-938
Ax
B938

x-939
Ax
B939

x-940
Ax
B940

x-941
Ax
B941

x-942
Ax
B942

x-943
Ax
B943

x-944
Ax
B944

x-945
Ax
B945

x-946
Ax
B946

x-947
Ax
B947

x-948
Ax
B948

x-949
Ax
B949

x-950
Ax
B950

x-951
Ax
B951

x-952
Ax
B952

x-953
Ax
B953

x-954
Ax
B954

x-955
Ax
B955

x-956
Ax
B956

x-957
Ax
B957

x-958
Ax
B958

x-959
Ax
B959

x-960
Ax
B960

x-961
Ax
B961

x-962
Ax
B962

x-963
Ax
B963

x-964
Ax
B964

x-965
Ax
B965

x-966
Ax
B966

x-967
Ax
B967

x-968
Ax
B968

x-969
Ax
B969

x-970
Ax
B970

x-971
Ax
B971

x-972
Ax
B972

x-973
Ax
B973

x-974
Ax
B974

x-975
Ax
B975

x-976
Ax
B976

x-977
Ax
B977

x-978
Ax
B978

x-979
Ax
B979

x-980
Ax
B980

x-981
Ax
B981

x-982
Ax
B982

x-983
Ax
B983

x-984
Ax
B984

x-985
Ax
B985

x-986
Ax
B986

x-987
Ax
B987

x-988
Ax
B988

x-989
Ax
B989

x-990
Ax
B990

x-991
Ax
B991

x-992
Ax
B992

x-993
Ax
B993

x-994
Ax
B994

x-995
Ax
B995

x-996
Ax
B996

x-997
Ax
B997

x-998
Ax
B998

x-999
Ax
B999

x-1001
Ax
B1001

x-1002
Ax
B1002

x-1003
Ax
B1003

x-1004
Ax
B1004

x-1005
Ax
B1005

x-1006
Ax
B1006

x-1007
Ax
B1007

x-1008
Ax
B1008

x-1009
Ax
B1009

x-1010
Ax
B1010

x-1011
Ax
B1011

x-1012
Ax
B1012

x-1013
Ax
B1013

x-1014
Ax
B1014

x-1015
Ax
B1015

x-1016
Ax
B1016

x-1017
Ax
B1017

x-1018
Ax
B1018

x-1019
Ax
B1019

x-1020
Ax
B1020

x-1021
Ax
B1021

x-1022
Ax
B1022

x-1023
Ax
B1023

x-1024
Ax
B1024

x-1025
Ax
B1025

x-1026
Ax
B1026

x-1027
Ax
B1027

x-1028
Ax
B1028

x-1029
Ax
B1029

x-1030
Ax
B1030

x-1031
Ax
B1031

x-1032
Ax
B1032

x-1033
Ax
B1033

x-1034
Ax
B1034

x-1035
Ax
B1035

x-1036
Ax
B1036

x-1037
Ax
B1037

x-1038
Ax
B1038

x-1039
Ax
B1039

x-1040
Ax
B1040

x-1041
Ax
B1041

x-1042
Ax
B1042

x-1043
Ax
B1043

x-1044
Ax
B1044

x-1045
Ax
B1045

x-1046
Ax
B1046

x-1047
Ax
B1047

x-1048
Ax
B1048

x-1049
Ax
B1049

x-1050
Ax
B1050

TABLE 8

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-1051
Ax
B1051

x-1052
Ax
B1052

x-1053
Ax
B1053

x-1054
Ax
B1054

x-1055
Ax
B1055

x-1056
Ax
B1056

x-1057
Ax
B1057

x-1058
Ax
B1058

x-1059
Ax
B1059

x-1060
Ax
B1060

x-1061
Ax
B1061

x-1062
Ax
B1062

x-1063
Ax
B1063

x-1064
Ax
B1064

x-1065
Ax
B1065

x-1066
Ax
B1066

x-1067
Ax
B1067

x-1068
Ax
B1068

x-1069
Ax
B1069

x-1070
Ax
B1070

x-1071
Ax
B1071

x-1072
Ax
B1072

x-1073
Ax
B1073

x-1074
Ax
B1074

x-1075
Ax
B1075

x-1076
Ax
B1076

x-1077
Ax
B1077

x-1078
Ax
B1078

x-1079
Ax
B1079

x-1080
Ax
B1080

x-1081
Ax
B1081

x-1082
Ax
B1082

x-1083
Ax
B1083

x-1084
Ax
B1084

x-1085
Ax
B1085

x-1086
Ax
B1086

x-1087
Ax
B1087

x-1088
Ax
B1088

x-1089
Ax
B1089

x-1090
Ax
B1090

x-1091
Ax
B1091

x-1092
Ax
B1092

x-1093
Ax
B1093

x-1094
Ax
B1094

x-1095
Ax
B1095

x-1096
Ax
B1096

x-1097
Ax
B1097

x-1098
Ax
B1098

x-1099
Ax
B1099

x-1100
Ax
B1100

x-1101
Ax
B1101

x-1102
Ax
B1102

x-1103
Ax
B1103

x-1104
Ax
B1104

x-1105
Ax
B1105

x-1106
Ax
B1106

x-1107
Ax
B1107

x-1108
Ax
B1108

x-1109
Ax
B1109

x-1110
Ax
B1110

x-1111
Ax
B1111

x-1112
Ax
B1112

x-1113
Ax
B1113

x-1114
Ax
B1114

x-1115
Ax
B1115

x-1116
Ax
B1116

x-1117
Ax
B1117

x-1118
Ax
B1118

x-1119
Ax
B1119

x-1120
Ax
B1120

x-1121
Ax
B1121

x-1122
Ax
B1122

x-1123
Ax
B1123

x-1124
Ax
B1124

x-1125
Ax
B1125

x-1126
Ax
B1126

x-1127
Ax
B1127

x-1128
Ax
B1128

x-1129
Ax
B1129

x-1130
Ax
B1130

x-1131
Ax
B1131

x-1132
Ax
B1132

x-1133
Ax
B1133

x-1134
Ax
B1134

x-1135
Ax
B1135

x-1136
Ax
B1136

x-1137
Ax
B1137

x-1138
Ax
B1138

x-1139
Ax
B1139

x-1140
Ax
B1140

x-1141
Ax
B1141

x-1142
Ax
B1142

x-1143
Ax
B1143

x-1144
Ax
B1144

x-1145
Ax
B1145

x-1146
Ax
B1146

x-1147
Ax
B1147

x-1148
Ax
B1148

x-1149
Ax
B1149

x-1150
Ax
B1150

x-1151
Ax
B1151

x-1152
Ax
B1152

x-1153
Ax
B1153

x-1154
Ax
B1154

x-1155
Ax
B1155

x-1156
Ax
B1156

x-1157
Ax
B1157

x-1158
Ax
B1158

x-1159
Ax
B1159

x-1160
Ax
B1160

x-1161
Ax
B1161

x-1162
Ax
B1162

x-1163
Ax
B1163

x-1164
Ax
B1164

x-1165
Ax
B1165

x-1166
Ax
B1166

x-1167
Ax
B1167

x-1168
Ax
B1168

x-1169
Ax
B1169

x-1170
Ax
B1170

x-1171
Ax
B1171

x-1172
Ax
B1172

x-1173
Ax
B1173

x-1174
Ax
B1174

x-1175
Ax
B1175

x-1776
Ax
B1176

x-1177
Ax
B1177

x-1178
Ax
B1178

x-1179
Ax
B1179

x-1180
Ax
B1180

x-1181
Ax
B1181

x-1182
Ax
B1182

x-1183
Ax
B1183

x-1184
Ax
B1184

x-1185
Ax
B1185

x-1186
Ax
B1186

x-1187
Ax
B1187

x-1188
Ax
B1188

x-1189
Ax
B1189

x-1190
Ax
B1190

x-1191
Ax
B1191

x-1192
Ax
B1192

x-1193
Ax
B1193

x-1194
Ax
B1194

x-1195
Ax
B1195

x-1196
Ax
B1196

x-1197
Ax
B1197

x-1198
Ax
B1198

x-1199
Ax
B1199

x-1200
Ax
B1200

TABLE 9

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-1201
Ax
B1201

x-1202
Ax
B1202

x-1203
Ax
B1203

x-1204
Ax
B1204

x-1205
Ax
B1205

x-1206
Ax
B1206

x-1207
Ax
B1207

x-1208
Ax
B1208

x-1209
Ax
B1209

x-1210
Ax
B1210

x-1211
Ax
B1211

x-1212
Ax
B1212

x-1213
Ax
B1213

x-1214
Ax
B1214

x-1215
Ax
B1215

x-1216
Ax
B1216

x-1217
Ax
B1217

x-1218
Ax
B1218

x-1219
Ax
B1219

x-1220
Ax
B1220

x-1221
Ax
B1221

x-1222
Ax
B1222

x-1223
Ax
B1223

x-1224
Ax
B1224

x-1225
Ax
B1225

x-1226
Ax
B1226

x-1227
Ax
B1227

x-1228
Ax
B1228

x-1229
Ax
B1229

x-1230
Ax
B1230

x-1231
Ax
B1231

x-1232
Ax
B1232

x-1233
Ax
B1233

x-1234
Ax
B1234

x-1235
Ax
B1235

x-1236
Ax
B1236

x-1237
Ax
B1237

x-1238
Ax
B1238

x-1239
Ax
B1239

x-1240
Ax
B1240

x-1241
Ax
B1241

x-1242
Ax
B1242

x-1243
Ax
B1243

x-1244
Ax
B1244

x-1245
Ax
B1245

x-1246
Ax
B1246

x-1247
Ax
B1247

x-1248
Ax
B1248

x-1249
Ax
B1249

x-1250
Ax
B1250

x-1251
Ax
B1251

x-1252
Ax
B1252

x-1253
Ax
B1253

x-1254
Ax
B1254

x-1255
Ax
B1255

x-1256
Ax
B1256

x-1257
Ax
B1257

x-1258
Ax
B1258

x-1259
Ax
B1259

x-1260
Ax
B1260

x-1261
Ax
B1261

x-1262
Ax
B1262

x-1263
Ax
B1263

x-1264
Ax
B1264

x-1265
Ax
B1265

x-1266
Ax
B1266

x-1267
Ax
B1267

x-1268
Ax
B1268

x-1269
Ax
B1269

x-1270
Ax
B1270

x-1271
Ax
B1271

x-1272
Ax
B1272

x-1273
Ax
B1273

x-1274
Ax
B1274

x-1275
Ax
B1275

x-1276
Ax
B1276

x-1277
Ax
B1277

x-1278
Ax
B1278

x-1279
Ax
B1279

x-1280
Ax
B1280

x-1281
Ax
B1281

x-1282
Ax
B1282

x-1283
Ax
B1283

x-1284
Ax
B1284

x-1285
Ax
B1285

x-1286
Ax
B1286

x-1287
Ax
B1287

x-1288
Ax
B1288

x-1289
Ax
B1289

x-1290
Ax
B1290

x-1291
Ax
B1291

x-1292
Ax
B1292

x-1293
Ax
B1293

x-1294
Ax
B1294

x-1295
Ax
B1295

x-1296
Ax
B1296

x-1297
Ax
B1297

x-1298
Ax
B1298

x-1299
Ax
B1299

x-1300
Ax
B1300

x-1301
Ax
B1301

x-1302
Ax
B1302

x-1303
Ax
B1303

x-1304
Ax
B1304

x-1305
Ax
B1305

x-1306
Ax
B1306

x-1307
Ax
B1307

x-1308
Ax
B1308

x-1309
Ax
B1309

x-1310
Ax
B1310

x-1311
Ax
B1311

x-1312
Ax
B1312

x-1313
Ax
B1313

x-1314
Ax
B1314

x-1315
Ax
B1315

x-1316
Ax
B1316

x-1317
Ax
B1317

x-1318
Ax
B1318

x-1319
Ax
B1319

x-1320
Ax
B1320

x-1321
Ax
B1321

x-1322
Ax
B1322

x-1323
Ax
B1323

x-1324
Ax
B1324

x-1325
Ax
B1325

x-1326
Ax
B1326

x-1327
Ax
B1327

x-1328
Ax
B1328

x-1329
Ax
B1329

x-1330
Ax
B1330

x-1331
Ax
B1331

x-1332
Ax
B1332

x-1333
Ax
B1333

x-1334
Ax
B1334

x-1335
Ax
B1335

x-1336
Ax
B1336

x-1337
Ax
B1337

x-1338
Ax
B1338

x-1339
Ax
B1339

x-1340
Ax
B1340

x-1341
Ax
B1341

x-1342
Ax
B1342

x-1343
Ax
B1343

x-1344
Ax
B1344

x-1345
Ax
B1345

x-1346
Ax
B1346

x-1347
Ax
B1347

x-1348
Ax
B1348

x-1349
Ax
B1349

x-1350
Ax
B1350

TABLE 10

[Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-1351
Ax
B1351

x-1352
Ax
B1352

x-1353
Ax
B1353

x-1354
Ax
B1354

x-1355
Ax
B1355

x-1356
Ax
B1356

x-1357
Ax
B1357

x-1358
Ax
B1358

x-1359
Ax
B1359

x-1360
Ax
B1360

x-1361
Ax
B1361

x-1362
Ax
B1362

x-1363
Ax
B1363

x-1364
Ax
B1364

x-1365
Ax
B1365

x-1366
Ax
B1366

x-1367
Ax
B1367

x-1368
Ax
B1368

x-1369
Ax
B1369

x-1370
Ax
B1370

x-1371
Ax
B1371

x-1372
Ax
B1372

x-1373
Ax
B1373

x-1374
Ax
B1374

x-1375
Ax
B1375

x-1376
Ax
B1376

x-1377
Ax
B1377

x-1378
Ax
B1378

x-1379
Ax
B1379

x-1380
Ax
B1380

x-1381
Ax
B1381

x-1382
Ax
B1382

x-1383
Ax
B1383

x-1384
Ax
B1384

x-1385
Ax
B1385

x-1386
Ax
B1386

x-1387
Ax
B1387

x-1388
Ax
B1388

x-1389
Ax
B1389

x-1390
Ax
B1390

x-1391
Ax
B1391

x-1392
Ax
B1392

x-1393
Ax
B1393

x-1394
Ax
B1394

x-1395
Ax
B1395

x-1396
Ax
B1396

x-1397
Ax
B1397

x-1398
Ax
B1398

x-1399
Ax
B1399

x-1400
Ax
B1400

x-1401
Ax
B1401

x-1402
Ax
B1402

x-1403
Ax
B1403

x-1404
Ax
B1404

x-1405
Ax
B1405

x-1406
Ax
B1406

x-1407
Ax
B1407

x-1408
Ax
B1408

x-1409
Ax
B1409

x-1410
Ax
B1410

x-1411
Ax
B1411

x-1412
Ax
B1412

x-1413
Ax
B1413

x-1414
Ax
B1414

x-1415
Ax
B1415

x-1416
Ax
B1416

x-1417
Ax
B1417

x-1418
Ax
B1418

x-1419
Ax
B1419

x-1420
Ax
B1420

x-1421
Ax
B1421

x-1422
Ax
B1422

x-1423
Ax
B1423

x-1424
Ax
B1424

x-1425
Ax
B1425

x-1426
Ax
B1426

x-1427
Ax
B1427

x-1428
Ax
B1428

x-1429
Ax
B1429

x-1430
Ax
B1430

x-1431
Ax
B1431

x-1432
Ax
B1432

x-1433
Ax
B1433

x-1434
Ax
B1434

x-1435
Ax
B1435

x-1436
Ax
B1436

x-1437
Ax
B1437

x-1438
Ax
B1438

x-1439
Ax
B1439

x-1440
Ax
B1440

x-1441
Ax
B1441

x-1442
Ax
B1442

x-1443
Ax
B1443

x-1444
Ax
B1444

x-1445
Ax
B1445

x-1446
Ax
B1446

x-1447
Ax
B1447

x-1448
Ax
B1448

x-1449
Ax
B1449

x-1450
Ax
B1450

x-1451
Ax
B1451

x-1452
Ax
B1452

x-1453
Ax
B1453

x-1454
Ax
B1454

x-1455
Ax
B1455

x-1456
Ax
B1456

x-1457
Ax
B1457

x-1458
Ax
B1458

x-1459
Ax
B1459

x-1460
Ax
B1460

x-1461
Ax
B1461

x-1462
Ax
B1462

x-1463
Ax
B1463

x-1464
Ax
B1464

x-1465
Ax
B1465

x-1466
Ax
B1466

x-1467
Ax
B1467

x-1468
Ax
B1468

x-1469
Ax
B1469

x-1470
Ax
B1470

x-1471
Ax
B1471

x-1472
Ax
B1472

x-1473
Ax
B1473

x-1474
Ax
B1474

x-1475
Ax
B1475

x-1476
Ax
B1476

x-1477
Ax
B1477

x-1478
Ax
B1478

x-1479
Ax
B1479

x-1480
Ax
B1480

x-1481
Ax
B1481

x-1482
Ax
B1482

x-1483
Ax
B1483

x-1484
Ax
B1484

x-1485
Ax
B1485

x-1486
Ax
B1486

x-1487
Ax
B1487

x-1488
Ax
B1488

x-1489
Ax
B1489

x-1490
Ax
B1490

x-1491
Ax
B1491

x-1492
Ax
B1492

x-1493
Ax
B1493

x-1494
Ax
B1494

x-1495
Ax
B1495

x-1496
Ax
B1496

x-1497
Ax
B1497

x-1498
Ax
B1498

x-1499
Ax
B1499

x-1500
Ax
B1500

TABLE 11

Group 1] Ir(L₁)₂(L₂)/

[Group 2] Ir(L₁)(L₂)₂

Compound
L₁
L₂

x-1501
Ax
B1501

x-1502
Ax
B1502

x-1503
Ax
B1503

x-1504
Ax
B1504

x-1505
Ax
B1505

x-1506
Ax
B1506

x-1507
Ax
B1507

x-1508
Ax
B1508

x-1509
Ax
B1509

x-1510
Ax
B1510

x-1511
Ax
B1511

x-1512
Ax
B1512

x-1513
Ax
B1513

x-1514
Ax
B1514

x-1515
Ax
B1515

x-1516
Ax
B1516

x-1517
Ax
B1517

x-1518
Ax
B1518

x-1519
Ax
B1519

x-1520
Ax
B1520

x-1521
Ax
B1521

x-1522
Ax
B1522

x-1523
Ax
B1523

x-1524
Ax
B1524

x-1525
Ax
B1525

x-1526
Ax
B1526

x-1527
Ax
B1527

x-1528
Ax
B1528

x-1529
Ax
B1529

x-1530
Ax
B1530

x-1531
Ax
B1531

x-1532
Ax
B1532

x-1533
Ax
B1533

x-1534
Ax
B1534

x-1535
Ax
B1535

x-1536
Ax
B1536

x-1537
Ax
B1537

x-1538
Ax
B1538

x-1539
Ax
B1539

x-1540
Ax
B1540

x-1541
Ax
B1541

x-1542
Ax
B1542

Among the compounds in Tables 1 to 11, a compound of Group 1 is represented by Ir(L₁)₂(L₂), and L₁and L₂among compounds represented by Ir(L₁)₂(L₂) of Group 1 are as described in Tables 1 to 11.

Among the compounds in Tables 1 to 11, a compound of Group 2 is represented by Ir(L₁)(L₂)₂, and L₁and L₂among compounds represented by Ir(L₁)(L₂)₂of Group 2 are as described in Tables 1 to 11.

x in Tables 1 to 11 is an integer from 1 to 380. Ax, i.e., A1 to A380, is as described above.

For example, in Tables 1 to 11,

1) Compound 93-10 (i.e., x=93) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A93 and L₂is B10, and may be represented by Compound 1 below,

2) Compound 298-58 (i.e., x=298) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A298 and L₂is B58, and may be represented by Compound 2 below,

3) Compound 260-373 (i.e., x=260) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A260 and L₂is B373, and may be represented by Compound 3 below,

4) Compound 198-1465 (i.e., x=198) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A198 and L₂is B1465, and may be represented by Compound 4,

5) Compound 1-1541 (i.e., x=1) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A1 and L₂is B1541, and may be represented Compound 5,

6) Compound 260-1542 (i.e., x=260) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A260 and L₂is B1542, and may be represented by Compound 6,

7) Compound 201-1070 (i.e., x=201) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A201 and L₂is B1070, and may be represented by Compound 7,

8) Compound 202-721 (i.e., x=202) of Group 1 is a compound represented by Ir(L₁)₂(L₂) in which L₁is A202 and L₂is B721, and may be represented by Compound 8, and

9) Compound 93-10 (i.e., x=93) of Group 2 is a compound represented by Ir(L₁)(L₂)₂in which L₁is A93 and L₂is B10, and may be represented by Compound 9:

[Image Omitted]

The remaining compounds in Tables 1 to 11 may also be recognized in the same manner as described above.

A composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described above may emit light (for example, light having an emission peak wavelength in a range of about 480 nm to about 580 nm, or about 510 nm to about 570 nm, such as green light, yellow-green light, or yellow light) having excellent luminescence efficiency and excellent lifespan. Thus, a layer including the composition, a light-emitting device including the composition, and an electronic apparatus including the light-emitting device may be provided.

According to another aspect, a layer including the composition including the first compound and the second compound as described above may be provided.

In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 480 nm to about 580 nm, for example, about 510 nm to about 570 nm.

In one or more embodiments, the layer may emit green light, yellow-green light, or yellow light.

In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 510 nm to about 540 nm.

In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 540 nm to about 570 nm.

A weight ratio of the first compound to the second compound included in the layer may be about 90:10 to about 10:90, about 80:20 to about 20:80, about 70:30 to about 30:70, or about 60:40 to about 40:60.

In one or more embodiments, a weight ratio of the first compound to second compound may be about 50:50, that is, about 1:1.

The layer may be formed i) by a co-deposition of the first compound and the second compound, or ii) by using a first mixture including the first compound and the second compound.

In one or more embodiments, the layer may include a host and a dopant, the host may not include a transition metal, and the dopant may include the composition including the first compound and the second compound. The layer may be formed i) by a co-deposition of the host and the dopant, or ii) by using a second mixture including the host and the dopant.

A weight of the host in the layer may be greater than a weight of the dopant.

In one or more embodiments, a weight ratio of the host to the dopant in the layer may be about 99:1 to about 55:45, or about 97:3 to about 60:40, or about 95:5 to about 70:30.

The host in the layer may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof.

According to another aspect, provided is a light-emitting device including: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition including the first compound and the second compound as described above.

The light-emitting device includes the composition including the first compound and the second compound as described above, and thus, may have excellent driving voltage, excellent external quantum efficiency, and excellent lifespan characteristics. Also, the light-emitting device may have an excellent side luminance ratio.

In one or more embodiments, the emission layer in the organic layer of the light-emitting device may include the composition including the first compound and the second compound.

In one or more embodiments, the emission layer may include a host and a dopant, the host may not include a transition metal, and the dopant may include the composition.

The host in the emission layer may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof.

In one or more embodiments, the host may include a hole transport compound and an electron transport compound, and the hole transport compound and the electron transport compound may be different from each other.

The emission layer may be formed by a co-deposition of the host and the dopant, or may be formed by using a second mixture including the host and the dopant.

The emission layer may emit third light having a third spectrum, and λP(EML) is an emission peak wavelength (in nm) of the third spectrum. In one or more embodiments, the λP(EML) may be evaluated from electroluminescence spectrum of the light-emitting device.

Fourth light having a fourth spectrum may be extracted to the outside of the light-emitting device (i.e., the organic light-emitting device) through the first electrode and/or the second electrode of the light-emitting device, and λP(OLED) is an emission peak wavelength (nm) of the fourth spectrum. In one or more embodiments, the λP(OLED) may be evaluated from electroluminescence spectrum of the light-emitting device.

In one or more embodiments, the λP(EML) and the λP(OLED) may each independently be about 480 nm to about 580 nm, for example, about 510 nm to about 570 nm.

In one or more embodiments, the λP(EML) and the λP(OLED) may each independently be about 510 nm to about 540 nm.

In one or more embodiments, the λP(EML) and the λP(OLED) may each independently be about 540 nm to about 570 nm.

In one or more embodiments, the third light and the fourth light may each be green light, yellow-green light, or yellow light.

In one or more embodiments, the third light and the fourth light may not be white light.

In one or more embodiments, the third spectrum may include i) a main emission peak having the λP(EML), and may not include ii) an additional emission peak having an emission peak wavelength of (λP(EML)+about 50 nm) or greater or (λP(EML)−about 50 nm) or less.

In one or more embodiments, the third spectrum may include i) a main emission peak having the λP(EML), and may not include ii) an additional emission peak having an emission peak wavelength of red light and/or blue light region.

In one or more embodiments, the fourth spectrum may include i) a main emission peak having the λP(OLED), and may not include ii) an additional emission peak having an emission peak wavelength of (λP(OLED)+about 50 nm) or greater or (λP(OLED)−about 50 nm) or less.

In one or more embodiments, the fourth spectrum may include i) a main emission peak having the λP(OLED), and may not include ii) an additional emission peak having an emission peak wavelength of red light and/or blue light region.

The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

In one or more embodiments, in the light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, the organic layer may further include a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

The term “organic layer” as used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode of the light-emitting device.

The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.

The FIGURE is a schematic cross-sectional view of a light-emitting device 10 according to one or more embodiments described herein. Hereinafter, the structure and manufacturing method of the light-emitting device 10 according to one or more embodiments will be described with reference to FIGURE. The light-emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

A substrate may be additionally located under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in light-emitting devices of the related art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.

The organic layer 15 is located on the first electrode 11.

The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

The hole transport region may be between the first electrode 11 and the emission layer.

The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, each layer is sequentially stacked in this stated order from the first electrode 11.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (L-B) deposition.

When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10⁻⁸torr to about 10⁻³torr, and a deposition rate of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec.

When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C.

The conditions for forming the hole transport layer and the electron blocking layer may be similar to or the same as the conditions for forming the hole injection layer.

The hole transport region may include 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB), 3-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or a combination thereof:

[Image Omitted]

In Formula 201, Ar₁₀₁and Ar₁₀₂may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₁-C₁₀alkylthio group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₇-C₆₀aryl alkyl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₂-C₆₀heteroaryl alkyl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.

xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.

R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉and R₁₂₁to R₁₂₄in Formulae 201 and 202 may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C₁-C₁₀alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group), a C₁-C₁₀alkoxy group(for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group), or a C₁-C₁₀alkylthio group;

a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, or a C₁-C₁₀alkylthio group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, or a combination thereof; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a C₁-C₁₀alkylthio group, or a combination thereof.

In Formula 201, R₁₀₉may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.

In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A:

[Image Omitted]

wherein R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉in Formula 201A are respectively as described above.

In one or more embodiments, the hole transport region may include one of Compounds HT1 to HT20 or a combination thereof:

[Image Omitted]

A thickness of the hole transport region may be in the range of about 100 angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

The charge-generation material may be, for example, a p-type dopant. The p-type dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or a combination thereof. For example, the p-type dopant may be: a quinone derivative such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; metal oxide, such as tungsten oxide and molybdenum oxide; a cyano group-containing compound, such as Compound HT-D1; or a combination thereof.

[Image Omitted]

The hole transport region may further include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, luminescence efficiency of a light-emitting device may be improved.

Meanwhile, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include a material that is used in the hole transport region as described above, a host material described below, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP, Compound H-H1, or a combination thereof may be used as the material for forming the electron blocking layer.

Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, L-B deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a material that is used to form the emission layer.

The emission layer may include the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described herein. In one or more embodiments, the emission layer may include a layer including the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described herein.

In one or more embodiments, the emission layer may include a host and a dopant, the host may not include a transition metal, and the dopant may include the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described herein.

The host may include 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN, also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), TCP, mCP, Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-H2, or a combination thereof:

[Image Omitted]

When the light-emitting device is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer.

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.

An electron transport region may be located on the emission layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (Balq), or a combination thereof:

[Image Omitted]

A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may include BCP, Bphen, TPBi, tris(8-hydroxyquinolinato)aluminum (Alq₃), Balq, 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or a combination thereof:

[Image Omitted]

In one or more embodiments, the electron transport layer may include one or more of Compounds ET1 to ET25, or a combination thereof:

[Image Omitted]

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 layer may include a metal-containing material in addition to the material as described above.

The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 or ET-D2:

[Image Omitted]

Also, the electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include LiF, NaCl, CsF, Li₂O, BaO, Compound ET-D1, Compound ET-D2, or a combination thereof.

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.

The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

In one or more embodiments, the composition, a layer including the composition, and an emission layer in a light-emitting device including the composition may not include a compound of [Group A] and mCP (1,3-bis(N-carbazolyl)benzene):

[Image Omitted]

Hereinbefore, the light-emitting device has been described in connection with FIGURE, but embodiments are not limited thereto.

According to another aspect, the light-emitting device may be included in an electronic apparatus. Thus, an electronic apparatus including the light-emitting device is provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, or the like.

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbons monovalent group having 1 to 60 carbon atoms, and the term “C₁-C₆₀alkylene group, as used here refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

Examples of the C₁-C₆₀alkyl group, the C₁-C₂₀alkyl group, and/or the C₁-C₁₀alkyl group may include a methyl group, an ethyl group, 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, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with at least one of a methyl group, an ethyl group, 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, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or a combination thereof. For example, Formula 9-33 is a branched C₆alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.

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

The term “C₁-C₆₀alkylthio group” as used herein refers to a monovalent group having the formula of —SA₁₀₁(where A₁₀₁is the C₁-C₆₀alkyl 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, a butenyl group, or the like. 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, a propynyl group, or the like. 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 cyclic group having 3 to 10 carbon atoms, and the C₃-C₁₀cycloalkylene group is a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

Examples of the C₃-C₁₀cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, or the like.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent saturated cyclic group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms, and the term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀heterocycloalkyl group.

Examples of the C₁-C₁₀heterocycloalkyl group may include a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, or the like.

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, a cycloheptenyl group, or the like. 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 hetero atom selected from N, O, P, Si, S, Se, Ge, and B 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 include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. 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, a chrysenyl group, or the like. 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 term “C₇-C₆₀alkyl aryl group” as used herein refers to a C₆-C₆₀aryl group substituted with at least one C₁-C₆₀alkyl group. The term “C₇-C₆₀aryl alkyl group” as used herein refers to a C₁-C₆₀alkyl group substituted with at least one C₆-C₆₀aryl group.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 1 to 60 carbon atoms, and the term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 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 two or more rings may be fused to each other.

The term “C₂-C₆₀alkyl heteroaryl group” as used herein refers to a C₁-C₆₀heteroaryl group substituted with at least one C₁-C₆₀alkyl group. The term “C₂-C₆₀heteroaryl alkyl group” as used herein refers to a C₁-C₆₀alkyl group substituted with at least one C₁-C₆₀heteroaryl group.

The term “C₆-C₆₀aryloxy group” as used herein indicates —OA₁₀₂(wherein A₁₀₂indicates the C₆-C₆₀aryl group), the term “C₆-C₆₀arylthio group” as used herein indicates —SA₁₀₃(wherein A₁₀₃indicates the C₆-C₆₀aryl group), and the term “C₁-C₆₀alkylthio group” as used herein indicates —SA₁₀₄(wherein A₁₀₄indicates the C₁-C₆₀alkyl group). The term “C₁-C₆₀heteroaryloxy group” as used herein indicates —OA_102′ (wherein A_102′ indicates the C₁-C₆₀heteroaryl group), and the term “C₁-C₆₀heteroarylthio group” as used herein indicates —SA_103′ (wherein A_103′ indicates the C₁-C₆₀heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. 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 (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, including at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or the like. 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 “C₅-C₃₀carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C₅-C₃₀carbocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C₅-C₃₀carbocyclic group (unsubstituted or substituted with at least one R_10a)” used herein are 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(norbornane) group, a bicyclo[2.2.2]octane group, 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, a cyclopentadiene group, or a fluorene group (each unsubstituted or substituted with at least one R_10a).

The term “C₁-C₃₀heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B other than 1 to 30 carbon atoms. The C₁-C₃₀heterocyclic group may be a monocyclic group or a polycyclic group. The “C₁-C₃₀heterocyclic group (unsubstituted or substituted with at least one R_10a)” may be, for example, a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole 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-fluoren-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-fluoren-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 isooxazole 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, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R_10a).

In one or more embodiments, examples of the “C₅-C₃₀carbocyclic group” and “C₁-C₃₀heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other,

the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and

the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

The terms “fluorinated C₁-C₆₀alkyl group (or a fluorinated C₁-C₂₀alkyl group or the like)”, “fluorinated C₃-C₁₀cycloalkyl group”, “fluorinated C₁-C₁₀heterocycloalkyl group,” and “fluorinated phenyl group” as used herein respectively indicate a C₁-C₆₀alkyl group (or a C₁-C₂₀alkyl group or the like), a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C₁alkyl group (that is, a fluorinated methyl group)” includes —CF₃, —CF₂H, and —CFH₂. The “fluorinated C₁-C₆₀alkyl group (or, a fluorinated C₁-C₂₀alkyl group, or the like)”, “the fluorinated C₃-C₁₀cycloalkyl group”, “the fluorinated C₁-C₁₀heterocycloalkyl group”, or “the fluorinated phenyl group” may be i) a fully fluorinated C₁-C₆₀alkyl group (or, a fully fluorinated C₁-C₂₀alkyl group, or the like), a fully fluorinated C₃-C₁₀cycloalkyl group, a fully fluorinated C₁-C₁₀heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen included therein is substituted with a fluoro group, or ii) a partially fluorinated C₁-C₆₀alkyl group (or, a partially fluorinated C₁-C₂₀alkyl group, or the like), a partially fluorinated C₃-C₁₀cycloalkyl group, a partially fluorinated C₁-C₁₀heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, all hydrogen included therein is not substituted with a fluoro group.

The terms “deuterated C₁-C₆₀alkyl group (or a deuterated C₁-C₂₀alkyl group or the like)”, “deuterated C₃-C₁₀cycloalkyl group”, “deuterated C₁-C₁₀heterocycloalkyl group,” and “deuterated phenyl group” as used herein respectively indicate a C₁-C₆₀alkyl group (or a C₁-C₂₀alkyl group or the like), a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C₁alkyl group (that is, the deuterated methyl group)” may include —CD₃, —CD₂H, and —CDH₂, and examples of the “deuterated C₃-C₁₀cycloalkyl group” are, for example, Formula 10-501 and the like. The “deuterated C₁-C₆₀alkyl group (or, the deuterated C₁-C₂₀alkyl group or the like)”, “the deuterated C₃-C₁₀cycloalkyl group”, “the deuterated C₁-C₁₀heterocycloalkyl group”, or “the deuterated phenyl group” may be i) a fully deuterated C₁-C₆₀alkyl group (or, a fully deuterated C₁-C₂₀alkyl group or the like), a fully deuterated C₃-C₁₀cycloalkyl group, a fully deuterated C₁-C₁₀heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein is substituted with at least one of deuterium, or ii) a partially deuterated C₁-C₆₀alkyl group (or, a partially deuterated C₁-C₂₀alkyl group or the like), a partially deuterated C₃-C₁₀cycloalkyl group, a partially deuterated C₁-C₁₀heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen included therein is not substituted with deuterium.

The term “(C₁-C₂₀alkyl) ‘X’ group” as used herein refers to a ‘X’ group that is substituted with at least one C₁-C₂₀alkyl group. For example, the term “(C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group” as used herein refers to a C₃-C₁₀cycloalkyl group substituted with at least one C₁-C₂₀alkyl group, and the term “(C₁-C₂₀alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C₁-C₂₀alkyl group. An example of a (C₁alkyl)phenyl group is a toluyl group.

The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” as used herein respectively refer to heterocyclic groups having the same backbones as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene 5,5-dioxide group,” in which, in each group, at least one carbon selected from ring-forming carbons is substituted with nitrogen.

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 C₁-C₆₀alkylthio 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 C₇-C₆₀alkyl aryl group, the substituted C₇-C₆₀aryl alkyl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₂-C₆₀alkyl heteroaryl group, the substituted C₂-C₆₀heteroaryl alkyl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio 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 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, or a C₁-C₆₀alkylthio group;

a C₁-C₆alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, or a C₁-C₆₀alkylthio 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 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, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —Ge(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), —P(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 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or 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 C₁-C₆₀alkylthio 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 C₇-C₆₀aryl alkyl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₂-C₆₀heteroaryl alkyl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —Ge(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), —P(Q₂₈)(Q₂₉), or a combination thereof;

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

a combination thereof.

Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉herein may 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 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 C₇-C₆₀aryl alkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₂-C₆₀heteroaryl alkyl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof.

For example, Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉described herein may each independently be:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH₂; 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 at least one of deuterium, a C₁-C₁₀alkyl group, a phenyl group, or a combination thereof.

Hereinafter, a compound and a light-emitting device according to one or more example embodiments are described in further detail with reference to Synthesis Example and Examples. However, the 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 1)

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Synthesis of Compound 1A

2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine (4.52 grams (g), 18.5 millimoles (mmol)) and iridium chloride hydrate (IrCl₃.(H₂O)_n, n=3) (2.96 g, 8.40 mmol) were mixed with 30 milliliters (mL) of 2-ethoxyethanol and 10 mL of deionized (DI) water and then stirred while heating at reflux for 24 hours, and then, the temperature was allowed to cool to room temperature. The resulting solid was separated by filtration, washed sufficiently with water, methanol, and hexanes, in this stated order, and then dried in a vacuum oven to obtain 5.22 g (yield of 87%) of Compound 1A.

Synthesis of Compound 1 B

Compound 1 Å (2.4 g, 1.68 mmol) and 60 mL of methylene chloride (MC) were mixed together, and then, silver trifluoromethanesulfonate (silver triflate, AgOTf) (0.86 g, 3.36 mmol) were mixed with 20 mL of methanol (MeOH) and then added thereto. Afterwards, the mixture was stirred for 18 hours at room temperature while light was blocked from the reaction contents with aluminum foil, and then the resulting product was filtered through diatomaceous earth to remove the resulting solid, and the filtrate was subjected to reduced pressure to obtain a resulting product (Compound 1 B). Compound 1 B was used in the next reaction without an additional purification process.

Synthesis of Compound 1

Compound 1B (2.66 g, 2.98 mmol) and Compound 1C (1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(7-phenyldibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole) (1.78 g, 2.98 mmol) were mixed with 30 mL of 2-ethoxyethanol and 30 mL of N,N-dimethylformamide and then stirred while heating at reflux for 48 hours, and then the temperature was allowed to cool to room temperature. The obtained mixture was subjected to a reduced pressure to obtain a solid, on which column chromatography (eluent: ethyl acetate (EA) and hexanes) was performed to obtain 1.13 g (yield of 30%) of Compound 1. The obtained compound was identified by high resolution mass spectrometry (HRMS) with matrix assisted laser desorption ionization (MALDI) and by high performance liquid chromatography (HPLC) analysis.

HRMS (MALDI) calcd for C₇₃H₆₅D₆IrN₄OSi₂: m/z 1274.5172 Found: 1274.5171.

Synthesis Example 2 (Synthesis of Compound 2)

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Synthesis of Compound 2A

6.3 g (yield of 90%) of Compound 2A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 2A(1) (2-(4-methyl-d3)phenyl-4-(propan-2-yl-2-d)-5-(trimethylgermyl)pyridine) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.

Synthesis of Compound 2B

Compound 2B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 2A was used instead of Compound 1A. The obtained Compound 2B was used in the next reaction without an additional purification process.

Synthesis of Compound 2

1.61 g (yield of 40%) of Compound 2 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 2B was used instead of Compound 1 B and Compound 2C (1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(7-fluorodibenzo[b,d]furan-4-yl)-1H-naphtho[1,2-d]imidazole) was used instead of Compound 1C.

HRMS (MALDI) calcd for C₇₇H₇₂D₈FIrN₄OGe₂: m/z 1444.4871 Found: 1444.4870.

Synthesis Example 3 (Synthesis of Compound 3)

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Synthesis of Compound 3A

6.13 g (yield of 88%) of Compound 3A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 3A(1) (2-phenyl-4-(propan-2-yl-2-d)-5-(trimethylgermyl)pyridine) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.

Synthesis of Compound 3B

Compound 3B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 3A was used instead of Compound 1A. The obtained Compound 3B was used in the next reaction without an additional purification process.

Synthesis of Compound 3

1.32 g (yield of 36%) of Compound 3 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 3B was used instead of Compound 1B and Compound 3C (8-(1-(2,6-diisopropylphenyl)-1H-benzo[d]imidazol-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) was used instead of Compound 1C.

HRMS (MALDI) calcd for C₆₅H₆₇D₅Ge₂IrN₅O: m/z 1284.4104 Found: 1281.4106.

Synthesis Example 4 (Synthesis of Compound 4)

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Synthesis of Compound 4A

4.31 g (yield of 81%) of Compound 4A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 4A(1) (4,5-bis(methyl-d3)-2-(6-(methyl-d3)-[1,1′-biphenyl]-3-yl)pyridine) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.

Synthesis of Compound 4B

Compound 4B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 4A was used instead of Compound 1A. The obtained Compound 4B was used in the next reaction without an additional purification process.

Synthesis of Compound 4

1.44 g (yield of 38%) of Compound 4 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 4B was used instead of Compound 1B and Compound 4C (8-(4-(2,2-dimethylpropyl-1,1-d2)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) was used instead of Compound 1C.

HRMS (MALDI) calcd for C₆₂H₃₄D₂₃IrN₄O: m/z 1089.5605 Found: 1089.5606.

Synthesis Example 5 (Synthesis of Compound 5)

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0.98 g (yield of 36%) of Compound 5 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 5B was used instead of Compound 1 B and Compound 5C was used instead of Compound 1C.

HRMS (MALDI) calcd for C₄₆H₅₆IrN₃Si₃: m/z 927.3411 Found: 927.3412.

Synthesis Example 6 (Synthesis of Compound 6)

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1.12 g (yield of 32%) of Compound 6 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 3B was used instead of Compound 1 B and Compound 6C was used instead of Compound 1C.

HRMS (MALDI) calcd for C₆₀H₆₂D₂Ge₂IrN₃O: m/z 1185.3228 Found: 1185.3226.

Synthesis Example 7 (Synthesis of Compound 7)

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Synthesis of Compound 7A

4.53 g (yield of 91%) of Compound 7A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that 2-phenyl-5-(trimethylgermyl)pyridine was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.

Synthesis of Compound 7B

Compound 7B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 7A was used instead of Compound 1A. The obtained Compound 7B was used in the next reaction without an additional purification process.

Synthesis of Compound 7

1.25 g (yield of 37%) of Compound 7 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 7B was used instead of Compound 1 B and Compound 7C was used instead of Compound 1C.

HRMS (MALDI) calcd for C₅H₅₄D₂Ge₂IrN₃O: m/z 1153.2602 Found: 1153.2600.

Synthesis Example 8: (Synthesis of Compound 8)

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Synthesis of Compound 8A

4.32 g (yield of 86%) of Compound 8A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 8A(1) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.

Synthesis of Compound 8B

Compound 8B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 8A was used instead of Compound 1A.

The obtained Compound 8B was used in the next reaction without an additional purification process.

Synthesis of Compound 8

1.49 g (yield of 36%) of Compound 8 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 8B was used instead of Compound 1 B and Compound 8C was used instead of Compound 1C.

HRMS (MALDI) calcd for C₇₅H₇₉Ge₂IrN₄O: m/z 1392.4307 Found: 1392.4305.

Manufacture of OLED 1

As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water, each for 5 minutes, and then cleaned by irradiation of ultraviolet light and exposure of ozone for 30 minutes. The resultant ITO-patterned glass substrate was loaded onto a vacuum deposition apparatus.

HT3 and F6-TCNNQ were vacuum co-deposited on the anode at the weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and then, HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å. H-H1 was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 300 Å.

Next, a host and a dopant were co-deposited on the electron blocking layer at a weight ratio described in Table 12 to form an emission layer having a thickness of 400 Å.

H-H1 and H-H2 were used at a weight ratio of 5:5 as the host, and the first compound and second compound described in Table 12 were used at a weight ratio of 1:1 as the dopant.

Afterwards, ET3 and ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, ET-D1 was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and A1 was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of OLED 1.

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Manufacture of OLEDs 2 to 6 and A to C

OLEDs 2 to 6 and A to C were manufactured in a similar manner as used to manufacture OLED 1, except that, in forming an emission layer, compounds described in Table 12 below were used as a dopant.

Evaluation Example 1

A driving voltage (volts, V), emission peak wavelength (λ_max, nm), maximum value of external quantum efficiency (Max EQE, relative % to OLED A), and lifespan (LT₉₇, relative % to OLED A) (hr) of each of OLEDs 1 to 6 and A to C were evaluated, and the results are shown in Tables 12 to 14. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as an apparatus for evaluation, the lifespan (LT₉₇) (at 16,000 candela per square meter (cd/m²) or nit) was obtained by measuring the amount of time (hour, hr) that elapsed until luminance was reduced to 97% of the initial brightness (from the initial luminance, which is set as 100%), and the results are expressed as a relative value (%) to OLED A. Max EQE of Tables 12 to 14 was also expressed as a relative value (%) to OLED A.

TABLE 12

Dopant in
Weight ratio

emission layer
of host to
Driving

Max EQE
LT₉₇

First
Second
dopant in
Voltage
λ_max
(Relative
(Relative

compound
compound
emission layer
(V)
(nm)
value, %)
value, %)

OLED 1
1
4
90:10
4.29
531
98
154

OLED 3
1
6
90:10
4.12
531
98
142

OLED 4
1
7
90:10
4.13
531
97
150

OLED A
1
95:5
4.00
531
100
100

OLED B
4
95:5
4.36
525
91
39

OLED C
C-1
C-2
90:10
5.4
516
42
<10

TABLE 13

Dopant in
Weight ratio

emission layer
of host to
Driving

Max EQE
LT₉₇

First
Second
dopant in
Voltage
λ_max
(Relative
(Relative

compound
compound
emission layer
(V)
(nm)
value, %)
value, %)

OLED 5
3
4
90:10
4.28
530
102
75

OLED 6
8
4
90:10
4.30
530
102
140

OLED B
4
95:5
4.36
525
91
39

OLED C
C-1
C-2
90:0
5.4
516
42
<10

TABLE 14

Dopant in
Weight ratio

emission layer
of host to
Driving

Max EQE
LT₉₇

First
Second
dopant in
Voltage
λ_max
(Relative
(Relative

compound
compound
emission layer
(V)
(nm)
value, %)
value, %)

OLED 2
2
5
90:10
4.15
525
86
85

OLED C
C-1
C-2
90:10
5.4
516
42
<10

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It was confirmed that 1) referring to Table 12, OLED 1 emits green light, and improved or equivalent external quantum efficiency and improved lifespan characteristics, compared to those of each of OLEDs A to C, 2) referring to Table 12, each of OLEDs 3 and 4 emit green light, and have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics compared to those of each of OLED C, 3) referring to Table 13, each of OLEDs 5 and 6 emit green light, and have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics compared to those of each of OLEDs B and C, and 3) referring to Table 14, OLED 2 emits green light, and has improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics compared to those of OLED C.

An electronic device, for example, a light-emitting device, including the composition may have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics.

It should be understood that the one or more exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more exemplary embodiments have been described with reference to the FIGURE, 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.