Triarylamine derivatives and their preparation methods, applications and devices

A technology of triarylamine and derivatives, which is applied in the field of triarylamine derivatives and their preparation, can solve the problems of low light extraction efficiency, and achieve the effects of high hole mobility, large commercial value, and good thermal stability

Active Publication Date: 2021-01-12
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, how to reduce the dissipation of light inside the device and improve the efficiency of light extraction is also a problem to be solved in the OLED field

Method used

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  • Triarylamine derivatives and their preparation methods, applications and devices
  • Triarylamine derivatives and their preparation methods, applications and devices
  • Triarylamine derivatives and their preparation methods, applications and devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] The compound (3) described in the present invention can be synthesized by the following method.

[0070] 1) In a 500ml three-necked flask, add N-phenylnaphthalene-2-amine (21.93g, 100mmol), 4'-bromo-4-iodobiphenyl (35.90g, 100mmol), toluene (200mL) and tert-butanol Sodium (28.83g, 300 mmol), the air was removed by ultrasonication, under the protection of nitrogen, palladium acetate (0.07g, 0.3mmol) and tri-tert-butylphosphine (0.18g, 0.6mmol) were added, and the reaction was heated under reflux at 115°C for 24 hours , TLC monitoring reaction is completed;

[0071] 2) After cooling to room temperature, wash with water twice, separate the liquids, dry the organic phase with anhydrous magnesium sulfate, filter, add activated carbon to the filtrate for decolorization at 115°C for 45 minutes, heat filter, and distill and concentrate the filtrate under reduced pressure with ethyl acetate The ester was recrystallized twice to finally obtain the intermediate N-(4'-bromo-[1,1'-...

Embodiment 2

[0075] The compound (12) described in the present invention can be synthesized by the following method.

[0076] 1) In a 500ml three-necked flask, add N-phenylpyridin-4-amine (17.02g, 100mmol) and 4'-bromo-4-iodobiphenyl (35.90g, 100mmol), toluene (200mL) and tert-butanol Sodium (28.83g, 300 mmol), ultrasonically remove the air, under the protection of nitrogen, add palladium acetate (0.07g, 0.3mmol) and tri-tert-butylphosphine (0.18g, 0.6mmol), heat and reflux at 115°C for 24 hours , TLC monitoring reaction is completed;

[0077] 2) After cooling to room temperature, wash with water twice, separate the liquids, dry the organic phase with anhydrous magnesium sulfate, filter, add activated carbon to the filtrate for decolorization at 115°C for 45 minutes, heat filter, and distill and concentrate the filtrate under reduced pressure with ethyl acetate The ester was recrystallized twice to finally obtain the intermediate N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylpyridin-4-amine 3...

Embodiment 3

[0081] The compound (22) described in the present invention can be synthesized by the following method.

[0082] 1) In a 500ml three-necked flask, add 9-phenyl-N-(4-methylphenyl)-9H-carbazol-3-amine (34.84g, 100mmol) and 4'-bromo-4-iodobiphenyl (35.90g, 100mmol), toluene (200mL) and sodium tert-butoxide (28.83g, 300mmol), ultrasonically removed the air, under the protection of nitrogen, added palladium acetate (0.07g, 0.3mmol) and tri-tert-butylphosphine (0.18 g, 0.6mmol), heated to reflux at 115°C for 24 hours, and TLC monitored the completion of the reaction;

[0083] 2) After cooling to room temperature, wash with water twice, separate the liquids, dry the organic phase with anhydrous magnesium sulfate, filter, add activated carbon to the filtrate for decolorization at 115°C for 45 minutes, heat filter, and distill and concentrate the filtrate under reduced pressure with ethyl acetate The ester was recrystallized twice to finally obtain the intermediate N-(4'-bromo-[1,1'-b...

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Abstract

The invention belongs to the technical field of photoelectric material application technology, and specifically relates to triarylamine derivatives and their preparation methods and applications. The triarylamine derivatives provided by the present invention use triarylamine and fluorenocarbazole as basic structural units, and obtain an asymmetric structure after modification, forming a class of compounds rich in holes and having a high glass transition temperature. When it is used as a hole transport material, it is compatible with hole transport materials commonly used in the prior art such as N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1' Compared with ‑biphenyl‑4,4'‑diamine (TPD), the hole transport ability is significantly improved. In organic electroluminescent devices, this series of compounds has higher starting voltage and glass The transition temperature has been significantly improved, and it is an ideal hole transport material. In addition, when the series of compounds are used as light-extracting layer materials, the efficiency of organic electroluminescent devices is greatly improved, and they are ideal light-extracting layer materials.

Description

technical field [0001] The invention belongs to the technical field of photoelectric material application technology, and specifically relates to triarylamine derivatives and their preparation methods, applications and devices. Background technique [0002] Organic Light-emitting Diode (Organic Light-emitting Diode) is also known as organic electroluminescent device or organic light-emitting display (Organic Light-emitting Display, OLED), the principle is a kind of positive, A display device prepared by the phenomenon that the negative electrode enters the organic solid light-emitting layer to recombine and emit light (Tang, C.W. et al. Appl. Phys. Lett. 1987, 52, 913). Devices mainly use organic small molecule / polymer semiconductor materials. Due to the characteristics of easy preparation, processing, purification and highly selective modification of organic small molecules and polymer materials, they have great potential in the field of material applications. They have bec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/94C07D405/12C07D401/12C07D403/12C07D405/14C07D401/14C09K11/06H01L51/50H01L51/54
CPCC07D209/94C07D405/12C07D401/12C07D403/12C07D405/14C07D401/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1044H10K85/636H10K85/633H10K85/615H10K85/631H10K85/6574H10K85/6572H10K50/15H10K50/11
Inventor 穆广园徐鹏庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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