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Arylamine compound having benzoazole ring structure, and organic electroluminescent element

An electroluminescent element, arylamine compound technology, applied in electroluminescent light sources, electrical components, organic semiconductor devices, etc., can solve the problem of low refractive index, low color purity, low light extraction efficiency in green and red light-emitting regions, etc. question

Pending Publication Date: 2021-09-10
HODOGOYA CHEMICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these conventional materials have problems of low refractive index in the green and red light-emitting regions and low light extraction efficiency.
[0011] In addition, for an element having a capping layer using a conventional material, since light with a wavelength of 400nm to 410nm of sunlight is transmitted and affects the material inside the element, there is also a decrease in color purity and light loss. The problem of the reduction of the take-out efficiency

Method used

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  • Arylamine compound having benzoazole ring structure, and organic electroluminescent element
  • Arylamine compound having benzoazole ring structure, and organic electroluminescent element
  • Arylamine compound having benzoazole ring structure, and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0216] (2-34)

[0217] Add 4-(naphthalen-2-yl)phenyl-amine: 7.5 g, 2-(4-bromophenyl)benzoxazole: 20.6 g, sodium tert-butoxide: 9.9 g, toluene: 150ml, while irradiating ultrasonic waves for 30 minutes, blow nitrogen gas. Tris(dibenzylideneacetone)dipalladium(0): 0.9 g and a 50% (w / v) toluene solution of tris-(tert-butyl)phosphine: 0.4 ml were added, and the mixture was stirred under heating and reflux for 3 hours. After natural cooling to 80°C, silica gel was added to filter, and the filtrate was concentrated to obtain a crude product. Recrystallization of the crude product from toluene afforded the yellow color of bis-{4-(benzoxazol-2-yl)phenyl}-{4-(naphthalen-2-yl)phenyl}amine (2-34) Powder: 6.3g (30% yield).

[0218] [chemical 11]

[0219]

[0220] The structure of the obtained yellow powder was identified using NMR.

[0221] Using 1H-NMR (CDCl 3 ) detected the following 27 hydrogen signals.

[0222] δ(ppm)=8.19-8.24(4H), 8.09(1H), 7.87-7.97(3H), 7.73-7.83(5H), 7.51-...

Embodiment 2

[0224] (2-39)

[0225] Add 4-(phenanthrene-9-yl)phenyl-amine: 8.0 g, 2-(4-bromophenyl)benzoxazole: 17.9 g, sodium tert-butoxide: 8.6 g, toluene: 160ml, while irradiating ultrasonic waves for 30 minutes, blow nitrogen gas. Tris(dibenzylideneacetone)dipalladium(0): 0.8 g and a 50% (w / v) toluene solution of tris-(tert-butyl)phosphine: 0.4 ml were added, and the mixture was stirred under reflux for 3 hours. After natural cooling to 80°C, silica gel was added to filter, and the filtrate was concentrated to obtain a crude product. The crude product was recrystallized from toluene to give bis-{4-(benzoxazol-2-yl)phenyl}-{4-(phenanthrene-9-yl)phenyl}amine (2-39) as a yellow Powder: 15.0 g (77.0% yield).

[0226] [chemical 12]

[0227]

[0228] The structure of the obtained yellow powder was identified using NMR.

[0229] use 1 H-NMR (CDCl 3 ) detected the following 29 hydrogen signals.

[0230] δ(ppm)=8.73-8.84(2H), 8.24-8.27(4H), 8.07-8.11(1H), 7.92-7.97(1H), 7.57-7.84(11H...

Embodiment 3

[0232] (2-44 )

[0233] Add ([1,1',2',1"]terphenyl-4'-yl)-amine: 5.6g, 2-(4-bromophenyl)benzoxazole: 14.4g, tert Sodium butoxide: 4.4g, toluene: 60ml, while irradiating ultrasonic waves for 30 minutes, feed nitrogen.Add palladium acetate: 0.1g, 50% (w / v) toluene solution of tri-(tert-butyl)phosphine: 0.4ml , stirred overnight under heating and reflux. After natural cooling, methanol was added to obtain the precipitated solid to obtain the crude product. The crude product was refined by crystallization using a toluene / acetone mixed solvent to obtain the precipitated solid to obtain bis- Yellow powder of {4-(benzoxazol-2-yl)phenyl}-([1,1',2',1"]terphenyl-4'-yl)-amine (2-44): 11.0 g (76.4% yield).

[0234] [chemical 13]

[0235]

[0236] The structure of the obtained yellow powder was identified using NMR.

[0237] use 1 H-NMR (DMSO-d 6 ) detected the following 29 hydrogen signals.

[0238] δ(ppm)=8.19(4H), 7.78(4H), 7.50(1H), 7.45-7.34(8H), 7.30(1H), 7.28-7.18(7H), 7....

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Abstract

The purpose of the present invention is to provide an organic EL element in which a capping layer is combined with various materials of the element so that properties of each of the materials of the element can be effectively demonstrated. The capping layer is constituted from a material that does not affect material inside the organic EL element when sunlight having wavelengths of 400-410 nm is absorbed, that has a high absorption coefficient and a high refractive index in order to greatly improve light extraction efficiency, that gives a thin film having excellent stability, durability and lightfastness, and that does not absorb light in the blue, green and red wavelength regions. The invention relates to: an arylamine compound having a benzoazole ring structure; and an organic EL element having a capping layer that contains the arylamine compound, and a luminescent layer that contains a host and a phosphorescent dopant.

Description

technical field [0001] The present invention relates to a compound of an organic electroluminescence element (hereinafter simply referred to as an organic EL element) which is a self-luminous element suitable for various display devices and the element, and specifically relates to an arylamine compound having a benzoxazole ring structure , and an organic EL device using the compound. 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, tris(8-quinolinolato)aluminum (hereinafter referred to as Alq3) and an aro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C09K11/06C07D209/82C07D263/62C07D277/66C07D251/24H01L51/50H05B33/24
CPCC07D209/82C07D251/24C07D263/62C07D277/66C07D405/14C09K11/06C09K2211/185H10K85/636H10K85/346H10K85/342H10K50/156H10K50/11H10K2101/10H10K2101/90H10K59/879H10K85/6572H10K85/6574H10K50/844H10K50/858C07D413/12C07D417/12H10K85/631H10K50/15H10K2102/351H10K85/654
Inventor 望月俊二上原卓也加濑幸喜平山雄太山本刚史林秀一崔英太李世珍朴锡培刘泰正梁炳善
Owner HODOGOYA CHEMICAL CO LTD
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