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A series of organic electroluminescent materials and their preparation methods and applications

A technology of light-emitting materials and organic light-emitting layers, applied in the fields of light-emitting materials, organic chemistry, silicon organic compounds, etc., to achieve the effects of good film-forming performance, lower start-up voltage, good fluorescence quantum efficiency and electroluminescence efficiency

Active Publication Date: 2016-08-17
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, organic electroluminescent display technology has become mature, and some products have entered the market. However, in the process of industrialization, there are still many problems to be solved, especially the various organic materials used to make devices. Injection, transmission performance, material electroluminescence performance, service life, color purity, matching between various materials and electrodes, etc., there are still many problems that have not yet been resolved.

Method used

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  • A series of organic electroluminescent materials and their preparation methods and applications
  • A series of organic electroluminescent materials and their preparation methods and applications
  • A series of organic electroluminescent materials and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1, the preparation of compound 006

[0075]

[0076] The first step: preparation of compound S-3

[0077]

[0078] 4.2g of S-2 was dissolved in 150ml of dry DMF, 2.8g of diboronic acid pinacol ester, 1.2g of anhydrous potassium acetate and 15mg of Pd(dppf)Cl were added 2 Catalyst, under the protection of nitrogen, heat up to 100 ° C, stir for 2 hours, cool to room temperature, pour the reaction solution into 500 ml of ice water, filter with suction, wash the filter cake with water, separate and purify the obtained solid with a silica gel column, and obtain 4.4 g of S-3, white solid.

[0079] The second step: the preparation of 4-(10-bromoanthracen-9-yl)pyridine

[0080]

[0081] 7.7 g of 4-pyridineboronic acid was dispersed with 50 ml of methanol and 150 ml of water, and 12.2 g of potassium bifluoride was added, and stirred and reacted at room temperature for 2 hours to obtain a clear solution, which was concentrated to dryness under reduced pressu...

Embodiment 2

[0090] Embodiment 2, the preparation of compound 009

[0091]

[0092] Take 2g of compound S-2 and 1.25g of N-phenyl-1-naphthylamine, 684mg of anhydrous sodium tert-butoxide, and 80ml of toluene, then add 50mg of tris(dibenzylideneacetone) dipalladium catalyst and 40mg 2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl, reflux under nitrogen protection overnight, cool to room temperature, add 50ml of water, separate the organic phase, extract the aqueous phase with DCM, organic phase reuse MgSO 4 After drying and suction filtration, the filtrate was concentrated to dryness under reduced pressure, and the residue was separated and purified by silica gel column to obtain 2.1 g of compound 009 as a white solid.

[0093] Experimental data:

[0094] (1) 1 HNMR (δ, CDCl 3 ): 6.62~6.65 (1H, q); 6.79~7.21 (17H, m); 7.34~7.45 (5H, m); 7.69~7.73 (3H, m); It is confirmed that the substance obtained by the reaction is indeed compound 009

[0095] (2) Glass transition temperature Tg:...

Embodiment 3

[0098] Embodiment 3, the preparation of compound 033

[0099]

[0100] The first step: the preparation of 4-bromotriphenylamine

[0101]

[0102] Disperse 27.2g of triphenylamine in 500ml of carbon tetrachloride, add 21.4g of NBS, raise the temperature and reflux and stir for 4 hours, cool to room temperature, filter with suction, concentrate the filtrate to dryness under reduced pressure, and recrystallize the residue with ethanol to obtain 30g 4-Bromotriphenylamine, white solid.

[0103] The second step: the preparation of N,N-diphenyl-4-(boronic acid pinacol ester) aniline

[0104]

[0105] With reference to the method in the first step of Example 1, S-2 is replaced with 4-bromotriphenylamine and 1.1 molar equivalents of pinacol ester of diboronic acid, 1.5 molar equivalents of anhydrous potassium acetate, 1% mole (with 4-bromotriphenylamine Triphenylamine as a base) palladium catalyst, and finally N,N-diphenyl-4-(boronic acid pinacol ester group) aniline, yellow...

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Abstract

The invention discloses a series of organic electroluminescent materials, and a preparation method and an application thereof. A structural formula of the materials is shown as a formula I. The organic electroluminescent materials shown as the formula I have capacities of electron transportation and hole transportation. An organic electroluminescent device prepared by using the materials has a reduced starting voltage. The series of the materials have relatively good fluorescent quantum efficiency and electroluminescent efficiency, and relatively good film-forming property. Besides, the method for material synthesis and purification is simple and suitable for large-scale production. The organic electroluminescent materials are ideal selection for blue-light emitting materials of the organic electroluminescent device. Applications of the organic electroluminescent materials as luminescent materials independently or as main materials or doping dyes in luminescent layers are also in a protection range. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and relates to an organic electroluminescence material and its preparation method and application. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, Pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display And other advantages, can be widely used in flat panel displays and surface light sources, so it has been ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/72C07D213/16C07C211/61C07C211/31C07C211/54C07D209/88C07D209/86C07D271/107C07D271/06C07D285/14C07D235/18C07D235/02C07D471/14C07F9/53C07F7/08C07D307/91C07D333/76C07D405/04C07D409/04C07D263/57C07D207/323C07D215/06C07D471/06C07D333/20C07D213/06C07D213/22C09K11/06H01L51/54
Inventor 曹建华郭剑李雅敏
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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