In the present disclosure, the preparation route of the organic compound is described below.

General Synthesis Formula

[Image Omitted]

In the preparation route, L1 to L4 are defined within the same range as L in Formula I, and A1 to A4 are defined within the same range as A in Formula I. In the preparation route, different symbols are used to represent that L and A in Formula I may be from L1 to L4 and A1 to A4 in different raw materials. In the preparation route, the number of -La-Ab (wherein a is an integer from 1 to 4, and b is an integer from 1 to 4) groups in each raw material may be an integer from 0 to 4, that is, the raw materials may be unsubstituted or substituted with multiple -La-Ab groups, but the total number of -La-Ab groups in each raw material must be at least 1.

A second aspect of the present disclosure is to provide an organic electroluminescent material including the organic compound as described in the first aspect.

A third aspect of the present disclosure is to provide a light-emitting layer material including the organic compound as described in the first aspect.

A fourth aspect of the present disclosure is to provide an OLED device including an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, where a material of the organic thin film layer includes the organic compound as described in the first aspect.

In one embodiment, the organic thin film layer includes a light-emitting layer which includes a host material and a doped material, wherein the host material includes the organic compound as described in the first aspect.

In the OLED device provided by the present disclosure, a material of the anode may be a metal, a metal oxide or a conductive polymer, wherein the metal includes copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc. as well as alloys thereof, the metal oxide includes indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide, indium gallium zinc oxide (IGZO), etc., and the conductive polymer includes polyaniline, polypyrrole, poly(3-methylthiophene), etc. In addition to the above materials that facilitate hole injection and combinations thereof, the material of the anode further includes known materials suitable for use as the anode.

In the OLED device, a material of the cathode may be a metal or a multilayer metal material, wherein the metal includes aluminum, magnesium, silver, indium, tin, titanium, etc. as well as alloys thereof, and the multilayer metal material includes LiF/Al, LiO₂/Al, BaF₂/Al, etc. In addition to the above materials that facilitate electron injection and combinations thereof, the material of the cathode further includes known materials suitable for use as the cathode.

In the OLED device, the organic thin film layer includes at least one light-emitting layer (EML) and any one or a combination of at least two of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL) or an electron injection layer (EIL) that are arranged on two sides of the at least one light-emitting layer. In addition to the organic compound as described in the first aspect of the present disclosure, the hole/electron injection and transport layers may also include carbazole compounds, arylamine compounds, benzimidazole compounds and metal compounds, etc. The OLED device may further be optionally provided with a capping layer

(CPL) disposed on the cathode (on a side of the cathode facing away from the anode).

The OLED device of the present disclosure may be prepared by the following method: forming the anode on a transparent or opaque smooth substrate, forming the organic thin film layer on the anode, and forming the cathode on the organic thin film layer. The organic thin film layer may be formed by using known film forming methods such as evaporation, sputtering, spin coating, impregnation and ion plating.

A fifth aspect of the present disclosure is to provide a display panel including the OLED device as described in the fourth aspect.

A sixth aspect of the present disclosure is to provide an organic light-emitting display device including the display panel as described in the fifth aspect.

Several preparation examples of the organic compound of the present disclosure are exemplarily described below.

PREPARATION EXAMPLES
Example 1

[Image Omitted]

(1) Synthesis of Intermediate f-1

Compound d-1 (80 mmol), Compound e-1 (85 mmol), potassium carbonate (0.3 mol), tetrahydrofuran (250 mL), water (120 mL) and tetrakis(triphenylphosphine)palladium (0.6 g) were added in sequence to a three-necked flask, heated to reflux for 12 h under nitrogen protection, cooled, extracted with dichloromethane, concentrated, and purified the crude product through column chromatography to obtain Intermediate f-1.

MALDI-TOF (m/z): C₁₆H₉ClO₃, whose calculated value was 284.02 and measured value was 284.00.

(2) Synthesis of Compound P13

Intermediate f-1 (50 mmol) and dry tetrahydrofuran (120 mL) were added in sequence to a three-necked flask, cooled to −70° C. under nitrogen protection, and slowly added with 3.0 M n-butyl lithium (20 mL). After the dropwise addition, the system was reacted for 1 h and then added with a solution (70 mL) of Compound c-1 (55 mmol) in tetrahydrofuran. After the addition, the system was slowly warmed to room temperature, reacted for 3 h, extracted with dichloromethane, concentrated, added with acetic acid (120 mL) and concentrated hydrochloric acid (3 mL), heated to reflux for 8 h and then cooled. The solvents were removed. The crude product was dissolved in dichloromethane and washed with water. The organic layer was dried and concentrated, and then purified through column chromatography to obtain Compound P13.

MALDI-TOF (m/z): C₄₃H₂₄N₂O₃, whose calculated value was 616.18 and measured value was 616.15.

Results of the elemental analysis of the compound: calculated value: C 83.75, H 3.92, N 4.54, O 7.78; measured value: C 83.74, H 3.93, N 4.54, O 7.78.

Example 2

[Image Omitted]

The preparation method of Compound P17 differs from step (2) in Example 1 in that Intermediate c-1 was replaced with an equimolar amount of c-2, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P17.

MALDI-TOF (m/z): C₄₄H₂₅N₃O₃, whose calculated value was 643.19 and measured value was 643.15.

Results of the elemental analysis of the compound: calculated value: C 82.10, H 3.91, N 6.53, O 7.46; measured value: C 82.10, H 3.91, N 6.53, O 7.46.

Example 3

[Image Omitted]

The preparation method of Compound P21 differs from step (2) in Example 1 in that Intermediate c-1 was replaced with an equimolar amount of c-3, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P21.

MALDI-TOF (m/z): C₅₀H₂₉N₃O₃, whose calculated value was 719.22 and measured value was 719.20.

Results of the elemental analysis of the compound: calculated value: C 83.43, H 4.06, N 5.84, O 6.67; measured value: C 83.42, H 4.07, N 5.84, O 6.67.

Example 4

[Image Omitted]

The preparation method of Intermediate f-2 differs from step (1) in Example 1 in that Intermediate d-1 was replaced with an equimolar amount of d-2 and Intermediate e-1 was replaced with an equimolar amount of e-2, while other raw materials, reaction steps and reaction conditions were the same as those in step (1) in Example 1, so as to obtain Compound f-2.

MALDI-TOF (m/z): C₁₆H₉ClO₂S, whose calculated value was 300.00 and measured value was 300.01.

The preparation method of Compound P33 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-2, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P33.

MALDI-TOF (m/z): C₄₃H₂₄N₂O₂S, whose calculated value was 632.16 and measured value was 632.12.

Results of the elemental analysis of the compound: calculated value: C 81.62, H 3.82, N 4.43, O 5.06, S 5.07; measured value: C, 81.61; H, 3.81; N, 4.44; O, 5.06; S, 5.07.

Example 5

[Image Omitted]

The preparation method of Compound P37 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-2 and Intermediate c-1 was replaced with an equimolar amount of c-2, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P37.

MALDI-TOF (m/z): C₄₄H₂₅N₃O₂S, whose calculated value was 659.17 and measured value was 659.14.

Results of the elemental analysis of the compound: calculated value: C 80.10, H 3.82, N 6.37, O 4.85, S 4.86; measured value: C 80.09, H 3.83, N 6.37, O 4.85, S 4.86.

Example 6

[Image Omitted]

The preparation method of Compound P41 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-2 and Intermediate c-1 was replaced with an equimolar amount of c-3, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P41.

MALDI-TOF (m/z): C₅₀H₂₉N₃O₂S, whose calculated value was 735.20 and measured value was 735.18.

Results of the elemental analysis of the compound: calculated value: C 81.61, H 3.97, N 5.71, O 4.35, S 4.36; measured value: C 81.60, H 3.98, N 5.71, O 4.35, S 4.36.

Example 7

[Image Omitted]

The preparation method of Compound P56 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-2 and Intermediate c-1 was replaced with an equimolar amount of c-4, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P56.

MALDI-TOF (m/z): C₃₇H₂₀N₂O₃, whose calculated value was 540.15 and measured value was 540.12.

Results of the elemental analysis of the compound: calculated value: C 82.21, H 3.73, N 5.18, O 8.88; measured value: C 82.20, H 3.74, N 5.18, O 8.88.

Example 8

[Image Omitted]

The preparation method of Intermediate f-3 differs from step (1) in Example 1 in that Intermediate d-1 was replaced with an equimolar amount of d-3 and Intermediate e-1 was replaced with an equimolar amount of e-3, while other raw materials, reaction steps and reaction conditions were the same as those in step (1) in Example 1, so as to obtain Compound f-3.

MALDI-TOF (m/z): C₂₂H₁₄ClNO₂, whose calculated value was 359.07 and measured value was 359.05.

The preparation method of Compound P87 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-3, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P87.

MALDI-TOF: (m/z): C₄₉H₂₉N₃O₂, whose calculated value was 691.23 and measured value was 632.10.

Results of the elemental analysis of the compound: calculated value: C 85.07, H 4.23, N 6.07, O 4.63; measured value: C 85.06, H 4.24, N 6.07, O 4.63.

Example 9 Synthesis of P47

[Image Omitted]

Synthesis of Intermediate d-5

Compound d-4 (60 mmol), Compound b-3 (65 mmol), potassium carbonate (0.3 mol), tetrahydrofuran (250 mL), water (120 mL) and tetrakis(triphenylphosphine)palladium (0.6 g) were added in sequence to a three-necked flask, heated to reflux for 12 h under nitrogen protection, cooled, extracted with dichloromethane, concentrated, and purified the crude product through column chromatography to obtain Intermediate d-5.

The preparation method of Intermediate f-4 differs from step (1) in Example 1 in that Intermediate d-1 was replaced with an equimolar amount of d-5 and Intermediate e-1 was replaced with an equimolar amount of e-2, while other raw materials, reaction steps and reaction conditions were the same as those in step (1) in Example 1, so as to obtain Compound f-4.

MALDI-TOF (m/z): C₃₇H₂₂ClN₃O₂S, whose calculated value was 607.11 and measured value was 607.10.

The preparation method of Compound P47 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-4, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound P47 was obtained.

MALDI-TOF (m/z): C₅₀H₂₉N₃O₂, whose calculated value was 735.20 and measured value was 735.18.

Results of the elemental analysis of the compound: calculated value: C 81.61, H 3.97, N 5.71, O 4.35, S 4.36; measured value: C 81.60, H 3.96, N 5.72, O 4.35, S 4.36.

Comparative Example 1
Synthesis of Comparative Compound

[Image Omitted]

[Image Omitted]

The preparation method of Compound M2 differs from step (2) in Example 1 in that Intermediate f-1 was replaced with an equimolar amount of f-2 and Intermediate c-1 was replaced with an equimolar amount of c-6, while other raw materials, reaction steps and reaction conditions were the same as those in step (2) in Example 1, so as to obtain Compound M2.

MALDI-TOF (m/z): C₄₇H₂₈O₂S, whose calculated value was 656.18 and measured value was 656.15.

Results of the elemental analysis of the compound: calculated value: C 85.96, H 4.31, O 4.86, S 4.88; measured value: C 85.95, H 4.30, O 4.87, S 4.88.

Device Example 1

This example provides an organic light-emitting device. As shown in FIG. 1, the organic light-emitting device includes a substrate 1, an ITO anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9 (magnesium-silver electrode, where a mass ratio of magnesium to silver is 9:1) and a capping layer (CPL) 10, wherein the ITO anode 2 has a thickness of 15 nm, the first hole transport layer 3 has a thickness of 10 nm, the second hole transport layer 4 has a thickness of 95 nm, the electron blocking layer 5 has a thickness of 30 nm, the light-emitting layer 6 has a thickness of 30 nm, the first electron transport layer 7 has a thickness of 30 nm, the second electron transport layer 8 has a thickness of 5 nm, the magnesium-silver electrode 9 has a thickness of 15 nm, and the capping layer (CPL) 10 has a thickness of 100 nm.

The OLED device was prepared by the steps below.

(1) A glass substrate 1 was cut into a size of 50 mm×50 mm×0.7 mm, sonicated in isopropyl alcohol and deionized water for 30 minutes separately, and then exposed to ozone for about 10 minutes for cleaning. The obtained glass substrate having the ITO anode 2 was installed onto a vacuum deposition apparatus.

(2) A hole buffer layer materials HT-1:HAT-CN was evaporated by means of vacuum evaporation on the ITO anode 2 to obtain a layer with a thickness of 10 nm, where the mass ratio of compound HT-1 to compound HAT-CN was 98:2, and the layer was used as a first hole transport layer 3.

(3) A second hole transport layer 4 material HT-1 was vacuum evaporated on the first hole transport layer 3 to obtain a layer with a thickness of 95 nm, and the layer was used as a second hole transport layer 4.

(4) A material Prime-1 was evaporated on the second hole transport layer 4 to obtain a layer with a thickness of 30 nm, and the layer was used as an electron blocking layer 5.

(5) A light-emitting layer 6 was co-deposited on the electron blocking layer 5, wherein the Organic Compound P13 provided by Example 1 of the present disclosure was used as a host material, Ir(piq)2(acac) was used as a doped material, the mass ratio of the Organic Compound P13 to Ir(piq)2(acac) was 19:1, and the thickness of the light-emitting layer was 30 nm.

(6) A Compound ET-1 of a first electron transport layer 7 was vacuum evaporated on the light-emitting layer 6 to obtain the first electron transport layer 7 with a thickness of 30 nm.

(7) A material LiF of a second electron transport layer 8 was vacuum evaporated on the first electron transport layer 7 to obtain the second electron transport layer 8 with a thickness of 5 nm.

(8) Magnesium and silver were vacuum evaporated on the second electron transport layer 8 to obtain the cathode 9 with a thickness of 15 nm, wherein a mass ratio of magnesium and silver was 9:1.

(9) A hole-type material CPL-1 with a high refractive index was vacuum evaporated on the cathode 9 for use as the cathode coating layer (capping layer or CPL) 10 with a thickness of 100 nm.

The materials HAT-CN, HT-1, Prime-1, Ir(piq)2(acac), ET-1 and CPL-1 mentioned in the above steps have the following structural formulas:

[Image Omitted]

Device Example 2

This device example differs from Device Example 1 only in that Organic Compound P13 in step (5) was replaced with an equivalent amount of Organic Compound P17 provided by the present disclosure. The other preparation steps were the same.

Device Example 3

This device example differs from Device Example 1 only in that Organic Compound P13 in step (5) was replaced with an equivalent amount of Organic Compound P21 provided by the present disclosure. The other preparation steps were the same.

Device Example 4

This device example differs from Device Example 1 only in that Organic Compound P13 in step (5) was replaced with an equivalent amount of Organic Compound P33 provided by the present disclosure. The other preparation steps were the same.

Device Example 5

This device example differs from Device Example 1 only in that Organic Compound P13 in step (5) was replaced with an equivalent amount of Organic Compound P37 provided by the present disclosure. The other preparation steps were the same.

Device Example 6

This device example differs from Device Example 1 only in that Organic Compound P13 in step (5) was replaced with an equivalent amount of Organic Compound P41 provided by the present disclosure. The other preparation steps were the same.