Compound having azabenzoxazole ring structure and organic electroluminescent element

A benzoxazole ring and compound technology, applied in the field of organic EL elements, can solve the problems of insufficient hole blocking function, lack of film stability, low electron transportability, etc., and achieve improved electron transport efficiency and excellent hole blocking ability. , the effect of high luminous efficiency

Pending Publication Date: 2021-05-14
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), which is known as an electron transport material, has a work function as large as 6.7 eV, and the hole blocking High capacity, but the glass transition temperature (Tg) is as low as 83°C, so it lacks the stability of the film, 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 azabenzoxazole ring structure and organic electroluminescent element
  • Compound having azabenzoxazole ring structure and organic electroluminescent element
  • Compound having azabenzoxazole ring structure and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138]

[0139] Charge 2-(4-chlorophenyl)-6-(10-phenyl-anthracen-9-yl)-7-azabenzoxazole: 4.1 g, 3-pyridylboronic acid: 1.1 g in the reaction vessel g, tris(dibenzylideneacetone) dipalladium (0): 0.6g, 50% (w / v) toluene solution of tris-(tert-butyl)phosphine: 1.0ml, cesium carbonate: 5.2g, at 1, 4-Dioxane / H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, add ethyl acetate / H 2 O, the organic layer was taken out by extraction and liquid separation, and concentrated to obtain a crude product. Purify the obtained crude product by column chromatography (carrier: silica gel, eluent: dichloromethane / ethyl acetate) to obtain 6-(10-phenyl-anthracene-9-yl)-2-(4 -Pale yellow powder of -pyridin-3-yl-phenyl)-7-azabenzoxazole (compound (5)): 3.2 g (yield: 71%).

[0140] [chemical 11]

[0141]

[0142] The structure of the obtained pale yellow powder was identified by NMR.

[0143] use 1 H-NMR (CDCl 3 ) detected the following 23 hydrogen signals.

[...

Embodiment 2

[0146]

[0147] Charge 2-(4-chlorophenyl)-6-(9,9'-spirobis[9H]fluoren-2-yl)-7-azabenzoxazole in the reaction vessel: 10.0 g, 4- (pyridin-3-yl)-phenylboronic acid: 4.4 g, tris(dibenzylideneacetone) dipalladium(0): 0.5 g, tricyclohexylphosphine: 0.3 g, tripotassium phosphate: 11.7 g, at 1, 4-Dioxane / H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, add ethyl acetate / H 2 O, the organic layer was taken out by extraction and liquid separation, and concentrated to obtain a crude product. By purifying the obtained crude product with column chromatography (carrier: silica gel, eluent: dichloromethane / ethyl acetate), 2-{4'-(pyridin-3-yl)-biphenyl-4- Light yellow powder of base}-6-(9,9'-spirobis[9H]fluoren-2-yl)-7-azabenzoxazole (compound (15)): 8.7g (yield: 71 %).

[0148] [chemical 12]

[0149]

[0150] The structure of the obtained pale yellow powder was identified by NMR.

[0151] use 1 H-NMR (CDCl 3 ) detected the following 29 hydrogen sig...

Embodiment 3

[0154]

[0155] Charge 2-(4-chlorophenyl)-6-(9,9'-spirobis[9H]fluoren-2-yl)-7-azabenzoxazole in the reaction vessel: 10.0 g, 3- (pyridin-3-yl)-phenylboronic acid: 4.4 g, tris(dibenzylideneacetone) dipalladium(0): 0.5 g, tricyclohexylphosphine: 0.3 g, tripotassium phosphate: 11.7 g, at 1, 4-Dioxane / H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, add ethyl acetate / H 2 O, the organic layer was taken out by extraction and liquid separation, and concentrated to obtain a crude product. By purifying the obtained crude product with column chromatography (carrier: silica gel, eluent: dichloromethane / ethyl acetate), 2-{3'-(pyridin-3-yl)-biphenyl-4- Light yellow powder of base}-6-(9,9'-spirobis[9H]fluoren-2-yl)-7-azabenzoxazole (compound (17)): 8.3g (yield: 68 %).

[0156] [chemical 13]

[0157]

[0158] For the obtained light yellow powder, the structure was identified using NMR.

[0159] use1 H-NMR (CDCl 3 ) detected the following 29 hydrogen...

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Abstract

A purpose of the present invention is to provide, as a material for organic EL elements having high efficiency and high durability, an organic compound which has excellent characteristics including excellent electron injection / transport performance, hole blocking ability and high stability in the form of a thin film; and another purpose of the present invention is to provide an organic EL element having high efficiency and high durability with use of this compound. A compound having an azabenzoxazole ring structure according to the present invention exhibits excellent heat resistance, while having good electron transport ability. An organic EL element which uses this compound in an electron transport layer, a hole blocking layer, a light emitting layer and an electron injection layer has exhibited good element characteristics.

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) as a self-luminous element suitable for various display devices. Specifically, it relates to a compound having an azabenzoxazole 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 and others from Eastman Kodak developed a layered structure device in which various functions are distributed to each material, thus making the organic EL device using organic materials a practical device. . They layered a phosphor capable of transporting electrons and an organic substance capable of transporting holes, injected the charges of the two into...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07D498/04
CPCC07D498/04Y02E10/549H10K85/626H10K85/615H10K85/654H10K85/657H10K50/16H10K85/656H10K50/171H10K50/18H10K50/11H10K30/353H10K85/6572H10K85/6574H10K85/6576
Inventor 加濑幸喜金是仁金志泳平山雄太
Owner HODOGOYA CHEMICAL CO LTD
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