Triarylamine derivative, preparation method, application and device thereof

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

Active Publication Date: 2019-07-05
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 derivative, preparation method, application and device thereof
  • Triarylamine derivative, preparation method, application and device thereof
  • Triarylamine derivative, preparation method, application and device thereof

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

Belonging to the technical field of photoelectric material applied science and technology, the invention in particular relates to a triarylamine derivative, a preparation method and application thereof. The triarylamine derivative provided by the invention adopts triarylamine and fluorenocarbazole as the basic structural unit, and after modification, an asymmetric structure can be obtained so as to compose compounds rich in holes and with high glass transition temperature. When the compounds are used as a hole transport material, compared with the commonly used hole transport material like N,N'-diphenyl-N, N'-bis(3-methylphenyl)-1, 1'-biphenyl-4, 4'-diamine (TPD) in the prior art, the hole transport ability is significantly improved, in OLEDs, the series of compounds have significantly improved starting voltage and glass transition temperature compared with the traditional hole transport materials, and are ideal hole transport materials. In addition, when the series of compounds are used as a light-emitting layer, the efficiency of OLEDs is greatly improved, and the series of compounds are ideal light-emitting 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 Applications(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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