Organic electroluminescent material based on tetraphenylhydrazine derivative and electronic device thereof

A technology of tetraphenylhydrazine and its derivatives, applied in the field of organic electroluminescent materials and electronic devices, can solve the problems of short life, low efficiency of electroluminescent materials, high cost, etc., and achieve improved life, low cost and long life Effect

Pending Publication Date: 2022-04-05
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 tetraphenylhydrazine derivatives and its electronic device, the purpose of which is to solve the problems of low efficiency, short life and high cost of electroluminescent materials in the prior art

Method used

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  • Organic electroluminescent material based on tetraphenylhydrazine derivative and electronic device thereof
  • Organic electroluminescent material based on tetraphenylhydrazine derivative and electronic device thereof
  • Organic electroluminescent material based on tetraphenylhydrazine derivative and electronic device thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Embodiment 1: the synthesis of compound 18

[0095] (Synthesis of Intermediate 1-1)

[0096] The synthetic route of intermediate 1-1 is as follows:

[0097]

[0098] Under nitrogen protection, potassium iodide (KI, 332 mg, 2 mmol), potassium periodate (KIO 4 , 6.9 g, 30 mmol), 4-bromodiphenylamine (5.0 g, 20 mmol) and 50 mL 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, 4.2 g of a white solid was obtained, with a yield of 85%. MS (EI): m / z: 494.10 [M+]. Anal.calcd for C24H18Br2N2(%): C 58.33, H 3.67, N 5.67; found: C 58.30, H3.70, N5.65.

[0099] (Synthesis of compound 18)

[0100] The synthetic route of compound 18 is as follows:

[0101]

[0102] Under nitrogen protection, intermediate 1-1 (2.5g, 5mm...

Embodiment 2

[0103] Embodiment 2: the synthesis of compound 12

[0104] (Synthesis of compound 12)

[0105] The synthetic route of compound 12 is as follows:

[0106]

[0107] Under nitrogen protection, intermediate 1-1 (2.5g, 5mmol), 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole were added successively in a 250mL Schlenk bottle ( 3.1 g, 11 mmol), palladium acetate (11 mg, 0.05 mmol), tri-tert-butylphosphine tetrafluoroborate (29 mg, 0.1 mmol), sodium tert-butoxide (1.9 g, 20 mmol), and 120 mL of toluene, stirred at reflux Reaction 12 Hour. After the reaction was complete, the solvent was evaporated, and the residue was dissolved with 200 mL of dichloromethane and 50 mL of water, washed with water, and the organic layer was separated. The aqueous layer was extracted twice with 15 mL of dichloromethane, and the organic layers were combined. After distilling off the solvent, the residue was separated by column chromatography (petroleum ether:dichloromethane=2:1 (V / V)). The solvent wa...

Embodiment 3

[0108] Embodiment 3: the synthesis of compound 11

[0109] (Synthesis of Intermediate 1-2)

[0110] The synthetic route of intermediate 1-2 is shown below:

[0111]

[0112] Under nitrogen protection, potassium iodide (KI, 332 mg, 2 mmol), potassium periodate (KIO 4 , 6.9g, 30mmol), 4-bromodiphenylamine (2.5g, 10mmol), diphenylamine (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, 2.9 g of a white solid was obtained, with a yield of 70%. MS (EI): m / z: 414.78 [M+]. Anal.calcd for C24H19BrN2(%): C 69.41, H 4.61, N 6.74; found: C 69.38, H 4.65, N 6.75.

[0113] (Synthesis of compound 11)

[0114] The synthetic route of compound 11 is as follows:

[0115]

[0116] Under nitrogen, add interme...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and provides an organic electroluminescent material based on tetraphenylhydrazine derivatives and an electronic device thereof. The tetraphenylhydrazine derivative has a structure as shown in a general formula (1), L1 and L2 independently represent a single bond, a carbonyl group, an aromatic hydrocarbon group with 6-18 carbon atoms or an aromatic heterocyclic group with 5-18 carbon atoms, and an electron donor group is introduced into the tetraphenylhydrazine rigid structure, so that the tetraphenylhydrazine derivative has the advantages that the electron donor group is introduced into the tetraphenylhydrazine rigid structure, and the electron donor group is introduced into the tetraphenylhydrazine rigid structure; the obtained tetraphenylhydrazine derivative has excellent film-forming property and thermal stability; the tetraphenylhydrazine derivative disclosed by the invention can also be used as a constituent material of a light-emitting layer, so that the driving voltage is reduced, the efficiency and the brightness are improved and the service life is prolonged. Besides, the preparation method of the tetraphenylhydrazine 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 tetraphenylhydrazine 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. In add...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/22C07C241/02C07D209/86C07D209/94C07D219/02C07D265/38C07D307/91C07D519/00C09K11/06H01L51/54H01L51/50
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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