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Aromatic amine compound and its preparation method and application

A technology of aromatic amines and compounds, applied in the field of organic electroluminescent materials, can solve the problems of thermal stability, fast hole mobility emitter efficiency and poor lifespan

Active Publication Date: 2017-10-24
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, when these aromatic amine compounds disclosed at present are used as electroluminescent materials, their thermal stability, fast hole mobility, luminous body efficiency and lifetime are relatively poor.

Method used

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  • Aromatic amine compound and its preparation method and application
  • Aromatic amine compound and its preparation method and application
  • Aromatic amine compound and its preparation method and application

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Experimental program
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preparation example Construction

[0099] The present invention also provides a preparation method of an aromatic amine compound having a structure of formula (I), comprising:

[0100] The compound with formula (II) structure is reacted with the compound of formula (III) structure, obtains the compound of formula (IV) structure,

[0101]

[0102] R 1 , R 3 independently selected from hydrogen, halogen, cyano, C1-C30 alkyl, C6-C50 aryl, C7-C50 arylalkyl, C7-C50 arylalkoxy, C7-C50 aryl Alkylmercapto or C5-C50 heteroaryl;

[0103] Ar 1 Arylene group selected from C6~C50,

[0104] The compound of formula (IV) is reacted with the compound of formula (V) to obtain the compound of formula (I).

[0105]

[0106] R 2 , R 4 independently selected from hydrogen, halogen, cyano, C1-C30 alkyl, C6-C50 aryl, C7-C50 arylalkyl, C7-C50 arylalkoxy, C7-C50 aryl Alkylmercapto or C5-C50 heteroaryl;

[0107] Ar 2 Arylene groups selected from C6 to C50.

[0108] According to the present invention, the present inventio...

Embodiment 1～27

[0125] 1) Preparation of formula (II-1) structural compound

[0126]

[0127] Add p-bromofluorobenzene (57.1mmol, 10g), 4-fluoroaniline (68.5mmol, 7.6g) into a 250mL three-necked flask, add tris(dibenzylideneacetone) bispalladium (1.7mmol, 0.98g) under nitrogen, tert-butyl Sodium alkoxide (114.2 mmol, 11 g), toluene 100 mL, stirred at room temperature for 30 min, tri-tert-butylphosphine (11.4 mmol, 2.3 g) was added under nitrogen protection and the temperature was raised to 80°C for 20 h. Extract with ethyl acetate, combine the organic phases and evaporate to dryness, then recrystallize with petroleum ether, pass the crude product through column chromatography, use petroleum ether / dichloromethane=5:1 as the eluent, evaporate the organic phases to obtain the formula (II The yield of bis(4-fluorophenyl)amine shown in -1) was 6.8 g, and the yield was 58%.

[0128] The synthetic method of formula (II-2) ~ formula (II-20) is similar to the synthetic method of formula (II-1), an...

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Abstract

The invention provides an aromatic amine compound, which has a structure of formula (I). The luminous efficiency of the compound provided by the invention is as high as 6.7cd / A when the current density is 20mA / cm2, and the service life can be as high as 6.7cd / A. Up to 6800 hours, much higher than the existing disclosed electroluminescent materials.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an aromatic amine compound and its preparation method and application. Background technique [0002] Since Tang et al. successfully prepared low-voltage-driven small molecule light-emitting devices in 1987, organic light-emitting technology has made great progress and has begun to enter the process of industrialization; among them, organic electroluminescent materials play a very important role in the performance of organic light-emitting devices. role. [0003] According to the molecular weight of organic electroluminescent materials, they can be divided into small molecule organic electroluminescent materials and high molecular organic electroluminescent materials. Among the currently disclosed luminescent materials, small molecule electroluminescent materials have high fluorescence quantum efficiency, are easy to purify, and have better luminous brightness ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/56C07C255/58C07C253/30C07C211/60C07C211/61C07D209/86C07C217/86C07C323/36C07C213/08C07C209/68C07C319/20C09K11/06H01L51/54
CPCC07C211/56C07C211/60C07C211/61C07C213/08C07C217/86C07C253/30C07C255/58C07C323/36C07D209/86C09K11/06
Inventor 高春吉张成成李国强胡晓明崔敦洙
Owner JILIN OPTICAL & ELECTRONICS MATERIALS