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Compound having benzazole ring structure, and organic electroluminescent device

A technology of benzoxazole ring and compound is applied in the fields of compounds with benzoxazole ring structure and organic electroluminescence elements, which can solve the problems of insufficient hole blocking function, lack of film stability, low electron transport, etc. Improved electron transport efficiency, excellent hole blocking ability, and high luminous efficiency

Pending Publication Date: 2021-07-30
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, low electron-transport property is a big problem in TAZ, and it is necessary to combine with an electron-transport material with higher electron-transport property to produce an organic EL device (see, for example, Non-Patent Document 5).
[0015] In addition, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), known as an electron transport material, has a work function as high as 6.7eV, and has a high hole blocking ability. However, the glass transition temperature (Tg) is as low as 83°C, so the stability of the film is lacking, and it cannot be said to fully function as a hole blocking layer.
[0016] All materials have insufficient film stability, or insufficient hole-blocking function

Method used

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  • Compound having benzazole ring structure, and organic electroluminescent device
  • Compound having benzazole ring structure, and organic electroluminescent device
  • Compound having benzazole ring structure, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156]

[0157] 2-(4-chlorophenyl)-4,6-bis(4-naphthalen-1-yl-phenyl)-benzoxazole: 8.8g, 4-cyanophenylboronic acid: 3.2g, three (dibenzylideneacetone) dipalladium (0): 0.3g, tricyclohexylphosphine: 0.4g, tripotassium phosphate: 5.4g, in 1,4-dioxane, H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, methanol was added into the system, dispersed, washed and filtered to obtain a crude product. Purify the obtained crude product by crystallization using a mixed solvent of chlorobenzene / acetone to obtain 4,6-bis(4-naphthalene-1-yl-phenyl)-2-(4'-cyano-biphenyl Pale yellow powder of -4-yl)-benzoxazole (compound-2): 7.2 g (yield: 83%).

[0158] [chemical 13]

[0159]

[0160] For the obtained pale yellow powder, NMR was used to identify the structure.

[0161] use 1 H-NMR (CDCl 3 ) detected the following 32 hydrogen signals.

[0162] δ(ppm)=8.52(2H), 8.33(2H), 8.13(1H), 8.05(1H), 8.04(1H), 8.01-7.88(7H), 7.85-7.78(6H), 7.75(2H), 7.70 (2H), 7.65-...

Embodiment 2

[0164]

[0165] 2-(4-chloro-phenyl)-4,6-bis(phenanthren-9-yl)-benzoxazole: 10.0g, 4-cyanophenylboronic acid: 3.0g, tris (Dibenzylideneacetone) dipalladium (0): 0.5g, tricyclohexylphosphine: 0.5g, tripotassium phosphate: 7.3g, in 1,4-dioxane, H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, methanol was added into the system, dispersed, washed and filtered to obtain a crude product. Purify the obtained crude product by recrystallization using a chlorobenzene solvent to obtain 4,6-bis(phenanthrene-9-yl)-2-(4'-cyano-biphenyl-4-yl)-benzo White powder of oxazole (compound-10): 4.0 g (yield: 36%).

[0166] [chemical 14]

[0167]

[0168] For the obtained white powder, the structure was identified using NMR.

[0169] use 1 H-NMR (CDCl 3 ) detected the following 28 hydrogen signals.

[0170] δ(ppm)=8.85(2H), 8.79(2H), 8.35(2H), 8.17(1H), 8.05(1H), 8.04(1H), 7.98(2H), 7.91(2H), 7.80-7.58(12H ), 7.65(2H), 7.59(1H)

Embodiment 3

[0172]

[0173]Charge 4,6-bis(naphthalen-1-yl)-2-(4-chloro-phenyl)-benzoxazole in the reaction vessel: 8.0 g, 4'-(4,4,5,5- Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-4-carbonitrile: 6.1g, Tris(dibenzylideneacetone)dipalladium(0):0.8g , tricyclohexylphosphine: 0.9g, tripotassium phosphate: 10.6g, in 1,4-dioxane, H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, water was added to the system for dispersion, washing and filtration to obtain a crude product. Purify the obtained crude product by recrystallization using a chlorobenzene solvent to obtain 4,6-bis(naphthalene-1-yl)-2-(4"-cyano-[1,1'; 4',1 ”] White powder of terphenyl-4-yl)-benzoxazole (compound-22): 9.3 g (yield: 90%).

[0174] [chemical 15]

[0175]

[0176] For the obtained white powder, the structure was identified using NMR.

[0177] use 1 H-NMR (CDCl 3 ) detected the following 28 hydrogen signals.

[0178] δ(ppm)=8.36(2H), 8.14(1H), 8.03(1H), 7.98(3H), 7.94(1H), 7.85(1H...

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Abstract

The purpose of the present invention is to provide, as a material for a high-efficiency and high-durability organic EL element, an organic compound having excellent electron injection / transport performance, hole blocking ability, and excellent characteristics of high stability in a thin film state, and to provide a high-efficiency and high-durability organic EL element using the compound. According to the present invention, various compounds having a benzoxazole ring structure are designed and chemically synthesized by focusing on the ability of a nitrogen atom of the benzoxazole ring structure having electron affinity to coordinate with a metal and having excellent heat resistance, and an organic EL element is trial-produced using these compounds, and as a result, characteristics are evaluated. It was found that an organic EL element having excellent characteristics can be obtained by using a compound having a specific benzoxazole ring structure.

Description

technical field [0001] The present invention relates to a compound and an element of an organic electroluminescent element (hereinafter simply referred to as an organic EL element) suitable for various display devices, in particular, to a compound having a benzoxazole ring structure and a compound using the Compound organic EL elements. Background technique [0002] Since the organic EL element is a self-luminous element, it is brighter than a liquid crystal element, has excellent visibility, and can perform a clear display, so active research has been conducted. [0003] In 1987, C.W.Tang of Eastman Kodak Co., Ltd. developed a layered structure element in which various functions are distributed to each material, thereby making an organic EL element using an organic material a practical element. They layered a phosphor capable of transporting electrons and an organic substance capable of transporting holes, injected the charges of the two into the layer of the phosphor to m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/02C07D413/10C07D421/14C07D471/04C09K11/06C07D263/57H01L51/50
CPCC07D263/57C07D413/10C07D471/04C09K11/06C07D413/14C07D413/04H10K85/615H10K85/654H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/165H10K50/18H10K85/656H10K50/16H10K50/171H10K50/11H10K85/622H10K85/624H10K85/626
Inventor 加濑幸喜金是仁金志泳平山雄太骏河和行林秀一
Owner HODOGOYA CHEMICAL CO LTD
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