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Aromatic amine derivatives, preparation method, and application thereof

A technology of aromatic amine derivatives and aryl groups, which is applied in the field of aromatic amine derivatives and their preparation, can solve the problems of lifespan and luminous efficiency constraints of OLED devices, reduce surface plasmon effect, improve transmittance, and increase luminous efficiency Effect

Active Publication Date: 2017-07-14
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These problems have restricted the lifespan and luminous efficiency of OLED devices, and have become a bottleneck for their widespread use.

Method used

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  • Aromatic amine derivatives, preparation method, and application thereof
  • Aromatic amine derivatives, preparation method, and application thereof
  • Aromatic amine derivatives, preparation method, and application thereof

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preparation example Construction

[0037] The present invention also provides a preparation method of the aromatic amine derivative, comprising:

[0038] The intermediate shown in formula (A) is reacted with the compound shown in formula (HO) to obtain the intermediate shown in formula (B):

[0039]

[0040] The intermediate shown in formula (B) is reacted with the bromide shown in formula (HT) again, obtains the aromatic amine derivative shown in formula (I):

[0041]

[0042] Among them, Ar 1 It is a C6-C18 aryl group, or a C10-C20 condensed aryl group with or without heteroatoms, Ar 2 It is a C6-C24 aryl group containing or not containing a heteroatom, or a C10-C20 condensed aryl group containing or not containing a heteroatom.

[0043] According to the present invention, the intermediate shown in formula (A) is prepared according to the method shown below:

[0044] Intermediate (A) is obtained by reacting 2,7-dibromo-9H-fluorenone (compound 1) with 9-phenyl-9H-carbazole (compound 2).

[0045]

...

Embodiment 1

[0057] Embodiment 1: the preparation of intermediate A

[0058] Under argon protection, 3.38g (10mmol) of 2,7-dibromo-9H-fluorenone (compound 1), 34g (140mmol) of 9-phenyl-9H- Carbazole (compound 2) and 0.96 g (10 mmol) of methanesulfonic acid were stirred at 140° C. for 6 hours. After the reaction, it was cooled to room temperature, extracted with dichloromethane, washed with saturated sodium bicarbonate solution and distilled water respectively, and the organic layer was concentrated to obtain a blue solid. The crude product was purified through a silica gel column using petroleum ether / dichloromethane (3:1) as eluent, and then recrystallized with acetone to obtain 6.29 g of intermediate A with a yield of 78%.

Embodiment 2

[0059] Embodiment 2: the preparation of intermediate B-1

[0060]

[0061] Under an argon atmosphere, 250 ml of dehydrated toluene was added to 40.33 g (50 mmol) of intermediate A, 9.31 g (100 mmol) of aniline, and 19.2 g (200 mmol) of sodium tert-butoxide, followed by stirring. 450 mg (2 mmol) of palladium acetate and 404 mg (2 mmol) of tri-tert-butylphosphine were added and reacted at 80° C. for 8 hours. After the reaction, it was cooled to room temperature, filtered through celite / silica gel, and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized from toluene, filtered, and dried to obtain 35.73 g of a solid, namely Intermediate B-1 (yield: 86%).

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Abstract

The invention provides aromatic amine derivatives, a preparation method, and an application thereof, and relates to the technical field of organic photoelectric materials. In the invention, 9,9-diphenylfluorene serves as a core, wherein the two phenyl groups, on the 9-position of the fluorene are modified with carbazole groups, and then the 2- and 7-positions of the fluorene are modified with arylamine groups, thereby obtaining a series of aromatic amine derivatives. The aromatic amine derivatives are easy to synthesize, have stable structure and excellent film forming performance, have higher light extraction efficiency and good hole transportation capability, and can be used as a light extraction layer in an OLED device and also can be used as a hole transportation layer. On one hand, the luminous efficiency of OLED devices is improved; and on the other hand, cost is effectively saved. The invention also provides the preparation method of the aromatic amine derivatives. The preparation method is simple and uses easy-to-obtained raw materials.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine derivative and its preparation method and application. Background technique [0002] Organic light-emitting diode (OLED) is a new generation of flat panel display technology following CRT, PDP, and LCD. The cost is low, and at the same time, it can make the display device ultra-thin and soft, so it has been developed rapidly in the past 20 years, and it is generally believed that it will be the mainstream of the next generation of display devices. At present, almost all internationally renowned electronic companies and chemical companies have invested huge manpower and funds into this research field, presenting a situation where research, development and industrialization go hand in hand. There are also some domestic telecommunications companies and companies specializing in organic electroluminescent display devices that have invested i...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D409/14C07D209/88C07D209/86C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/86C07D209/88C07D405/14C07D409/14C09K2211/1029C09K2211/1092C09K2211/1088C09K2211/1022C09K2211/1014C09K2211/1011C09K2211/1007H10K85/626H10K85/6576H10K85/6574H10K85/6572H10K50/15H10K50/11
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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