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A kind of aromatic amine derivative and its preparation method and application

A technology of aromatic amine derivatives and organic substances, applied in the field of aromatic amine derivatives and their preparation, can solve the problem that light extraction materials cannot meet the performance requirements of OLEDs

Active Publication Date: 2019-04-05
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of this, the present invention provides an aromatic amine derivative and its preparation method and application in order to solve the technical problem that the light extraction material in the prior art cannot meet the performance requirements of OLED

Method used

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  • A kind of aromatic amine derivative and its preparation method and application
  • A kind of aromatic amine derivative and its preparation method and application
  • A kind of aromatic amine derivative and its preparation method and application

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preparation example Construction

[0040] The present invention also provides a preparation method of the aromatic amine derivative, comprising:

[0041] Using 1,3-dibromo-2-(2,6-dibromophenyl)benzene as the starting material, react with methyl chloroformate to obtain intermediate (A); intermediate (A) undergoes reduction reaction to obtain intermediate Body (B); Intermediate (B) is methylated to obtain Intermediate (C); Intermediate (C) and methylene bromide undergo a ring-forming reaction to obtain Intermediate (D):

[0042]

[0043] Combining intermediate (D) with Ar 1 The aromatic amine compound reaction of substituent, obtains intermediate (E); Then intermediate (E) and containing Ar 2 The bromide reaction of substituent can obtain the aromatic amine derivative shown in formula (I):

[0044]

[0045] Among them, Ar 1 、Ar 2 is a substituted or unsubstituted C6-C24 aryl group or a substituted or unsubstituted C6-C24 heteroaryl group.

[0046] The present invention has no special restrictions on th...

Embodiment 1

[0052] Embodiment 1: the preparation of intermediate A

[0053] Dissolve 65g (140mmol) of 1,3-dibromo-2-(2,6-dibromophenyl)benzene and 16g (168mmol) of methyl chloroformate in 120ml of anhydrous tetrahydrofuran, then add dropwise 140ml of 1.6 M n-hexane solution of n-butyl lithium was stirred overnight at room temperature. After the reaction was finished, it was filtered with suction, washed with ethanol, and dried to obtain 38 g (112 mmol) of solid, namely intermediate A, with a yield of 78%.

Embodiment 2

[0054] Embodiment 2: the preparation of intermediate B

[0055] Add 38g (112mmol) of intermediate A to a vigorously stirred mixed solution of 600ml of toluene and 1200ml of ethanol, add 29ml (590mmol) of hydrazine hydrate, then add 1.8g of Raney nickel, and heat to reflux for 2 hours. Cool to room temperature, distill off the solvent under reduced pressure, dissolve the residue in 590ml of warm chloroform, filter through silica gel to obtain a clear solution, concentrate the solution to 59ml, add 177ml of ethanol, leave the mixture for 12 hours, and obtain crystals by suction filtration. Recrystallized twice in chloroform / ethanol to obtain 36 g (109 mmol) of intermediate B, yield 98%.

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Abstract

The invention provides an aromatic amine derivative, a preparation method and application thereof, and relates to the technical field of organic photoelectric materials. The compound is a series of aromatic amine derivatives obtained by using fluorene derivatives as the core structure and modifying the 9-position of fluorene with aromatic amines. This type of compound has a stable structure, excellent film-forming performance, higher light extraction efficiency and better hole transport ability, and can be used as a light extraction layer in OLED devices, and can also be used as a hole transport layer at the same time. Not only can the luminous efficiency of the OLED device be improved, but also the cost can be effectively saved. The invention also provides a preparation method of the aromatic amine derivative, the preparation method is simple and the raw materials are readily available.

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 electroluminescent device (OLED) is a new type of flat display device, which has energy saving, fast response, stable color, strong environmental adaptability, no radiation, wide range of material selection, low driving voltage, luminous efficiency and luminous brightness It has the characteristics of high height, wide viewing angle, long life, light weight, relatively simple production process, and low cost. At the same time, it can make the display device ultra-thin and flexible, which is in line with the current theme of green and environmental technology development. Therefore, in the past 20 years It has developed rapidly in the past few years, and is generally considered to be the mainstream of the next generation of display devices. Due to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/54C07C211/56C07C211/58C07C217/84C07D209/88C07D307/91C07D333/76H01L51/54
CPCC07C211/54C07C211/56C07C211/58C07C217/84C07D209/88C07D307/91C07D333/76H10K85/622H10K85/636H10K85/633H10K85/6574H10K85/6576H10K85/6572
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD