Organic electroluminescent material based on carbazole-9-yl-diphenylamine derivative and electronic device thereof

A technology of diphenylamine and derivatives, which is applied in the field of organic electroluminescent materials and electronic devices, can solve the problems of insufficient light-emitting layer composition, low luminous efficiency, and high driving voltage, and achieve low cost, simple preparation method, and high driving voltage. low effect

Pending Publication Date: 2022-03-22
维思普新材料(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention provides an organic electroluminescent material based on carbazol-9-yl-diphenylamine derivatives and its electronic device. The device structure of the material shows low luminous efficiency, high driving voltage, short life, and the material composition of the light-emitting layer is not good enough.

Method used

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  • Organic electroluminescent material based on carbazole-9-yl-diphenylamine derivative and electronic device thereof
  • Organic electroluminescent material based on carbazole-9-yl-diphenylamine derivative and electronic device thereof
  • Organic electroluminescent material based on carbazole-9-yl-diphenylamine derivative and electronic device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Embodiment 1: the synthesis of compound 3

[0093] (Synthesis of Intermediate 1-1)

[0094] The synthetic route of intermediate 1-1 is as follows:

[0095]

[0096] Under nitrogen protection, potassium iodide (KI, 332 mg, 2 mmol), potassium periodate (KIO 4 , 6.9g, 30mmol), 4,4'-dibromodiphenylamine (3.3g, 10mmol), carbazole (1.7g, 10mmol) and 50mL of anhydrous acetonitrile (MeCN), and react overnight at room temperature. After the reaction was completed, the solvent was evaporated under reduced pressure, and the crude product was further purified by column chromatography (petroleum ether:dichloromethane=4:1 (V / V)). After distilling off the solvent, 3.4 g of white solid was obtained, with a yield of 70%. MS (EI): m / z: 491.87 [M + ]. Anal.calcd for C 24 h 16 Br 2 N 2 (%): C 58.56, H 3.28, N 5.69; found: C 58.54, H 3.30, N 5.66.

[0097] (Synthesis of compound 3)

[0098] The synthetic route of compound 3 is as follows:

[0099]

[0100] Under nitrogen p...

Embodiment 2

[0101] Embodiment 2: the synthesis of compound 14

[0102] (Synthesis of Intermediate 1-2)

[0103] The synthetic route of intermediate 1-2 is shown below:

[0104]

[0105] Under nitrogen protection, potassium iodide (KI, 332 mg, 2 mmol), potassium periodate (KIO 4 , 6.9g, 30mmol), diphenylamine (1.7g, 10mmol), 3,6-dibromocarbazole (3.3g, 10mmol) and 50mL of anhydrous acetonitrile (MeCN), and react overnight at room temperature. After the reaction was completed, the solvent was evaporated under reduced pressure, and the crude product was further purified by column chromatography (petroleum ether:dichloromethane=4:1 (V / V)). After distilling off the solvent, 3.6 g of white solid was obtained, with a yield of 74%. MS (EI): m / z: 491.76 [M + ]. Anal.calcd for C 24 h 16 Br 2 N 2 (%): C 58.56, H 3.28, N 5.69; found: C 58.53, H 3.32, N 5.67.

[0106] (Synthesis of Compound 14)

[0107] The synthetic route of compound 14 is as follows:

[0108]

[0109] Under nitroge...

Embodiment 3

[0110] Embodiment 3: the synthesis of compound 18

[0111] (Synthesis of Intermediates 1-3)

[0112] The synthetic routes of intermediates 1-3 are shown below:

[0113]

[0114] Under nitrogen protection, potassium iodide (KI, 332 mg, 2 mmol), potassium periodate (KIO 4 , 6.9g, 30mmol), 4-bromodiphenylamine (2.5g, 10mmol), 3-bromocarbazole (2.5g, 10mmol) and 50mL of anhydrous acetonitrile (MeCN), and react overnight at room temperature. After the reaction was completed, the solvent was evaporated under reduced pressure, and the crude product was further purified by column chromatography (petroleum ether:dichloromethane=4:1 (V / V)). After distilling off the solvent, 3.9 g of a white solid was obtained, with a yield of 79%. MS(EI): m / z: 492.08[M + ]. Anal.calcd for C 24 h 16 Br 2 N 2 (%): C 58.56, H 3.28, N 5.69; found: C 58.55, H 3.29, N 5.66.

[0115] (Synthesis of Compound 18)

[0116] The synthetic route of compound 18 is as follows:

[0117]

[0118] Under ...

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Abstract

The invention relates to the technical field of organic photoelectric materials, and provides an organic electroluminescent material based on carbazole-9-yl-diphenylamine derivatives and an electronic device thereof. The carbazole-9-yl-diphenylamine derivative disclosed by the invention has a structure as shown in a general formula (1), wherein L1 to L4 independently represent a single bond, a carbonyl group, an aromatic hydrocarbon group with 6 to 18 carbon atoms or an aromatic heterocyclic group with 5 to 18 carbon atoms; an electron donor group is introduced into a carbazole-9-yl-diphenylamine rigid structure, so that the obtained carbazole-9-yl-diphenylamine derivative is excellent in film forming property and thermal stability. The carbazole-9-yl-diphenylamine derivative disclosed by the invention can be used as a constituent material of a light-emitting layer, and can reduce driving voltage, improve efficiency, brightness, prolong the service life and the like. Besides, the preparation method of the carbazole-9-yl-diphenylamine derivative is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic electroluminescent material based on carbazol-9-yl-diphenylamine derivatives and an electronic device thereof. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminescence, low-voltage drive, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not need a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] An organic electroluminescent device generally includes an anode, a metal cathode, and an organic layer sandwiched between them. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D405/14C07D413/14C07D401/12C07D401/14C07D471/04C09K11/06H01L51/54H01L51/50
CPCC07D209/86C07D405/14C07D413/14C07D401/12C07D401/14C07D471/04C09K11/06C09K2211/1033C09K2211/1029C09K2211/1088C09K2211/1044H10K85/657H10K85/6574H10K85/6572
Inventor 朱向东刘向阳袁晓冬陈华
Owner 维思普新材料(苏州)有限公司
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