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Compound having benzotriazole ring structure and organic electroluminescence element

A technology of benzotriazole rings and compounds, which is applied in the fields of compounds with benzotriazole ring structures and organic electroluminescent elements, and can solve the problems of inability to fully exert functions, insufficient hole blocking functions, and glass transition Low temperature and other problems, to achieve the effect of excellent hole blocking ability, good injection characteristics, and improved luminous brightness

Pending Publication Date: 2021-12-14
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, the work function of bathocuproine (hereinafter referred to as BCP) is as high as 6.7eV, and the hole blocking ability is high, but the glass transition temperature (Tg) is as low as 83°C, so it lacks the stability of the film, so it can be used as a hole blocking layer. , cannot be said to fully function
[0016] All materials have insufficient film stability or insufficient hole blocking function

Method used

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  • Compound having benzotriazole ring structure and organic electroluminescence element
  • Compound having benzotriazole ring structure and organic electroluminescence element
  • Compound having benzotriazole ring structure and organic electroluminescence element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144]

[0145] Charge 2-(4-chloro-phenyl)-5-(9,9'-spirobis[9H]fluoren-2-yl)-2H-benzotriazole in the reaction vessel: 9.0 g, 4-cyano Base-phenylboronic acid: 2.9g, tris(dibenzylideneacetone) dipalladium (0): 0.5g, tricyclohexylphosphine: 0.2g, tripotassium phosphate: 10.5g, in 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 taken out by extraction and liquid separation was concentrated. The obtained concentrate was purified by column chromatography (carrier: silica gel, eluent: dichloromethane / n-heptane) to obtain 2-(4'-cyano-biphenyl-4-yl)-5- 8.1 g of (9,9'-spirobis[9H]fluoren-2-yl)-2H-benzotriazole (compound-2) yellow powder (yield: 80%).

[0146] [chemical 12]

[0147]

[0148] The structure of the obtained yellow powder was identified using NMR.

[0149] use 1 H-NMR (CDCl 3 ) detected the following 26 hydrogen signals.

[0150] δ(ppm)=8.46(2H), 7.97(2H), 7.94(1H), 7.90(3H),...

Embodiment 2

[0152]

[0153] Put 2-(4-bromophenyl)-5,6-dichloro-benzotriazole in the reaction vessel: 20.0g, 4'-(4,4,5,5-tetramethyl-[1, 3,2] dioxaborolan-2-yl)biphenyl-4-carbonitrile: 18.7g, toluene: 210mL, ethanol: 70mL, then, add potassium carbonate: 9.7g dissolved in H 2 O: an aqueous solution in 70 mL, nitrogen gas was passed through while irradiating ultrasonic waves for 30 minutes. Add tetrakis(triphenylphosphine)palladium: 1.7 g to the solution blown with nitrogen, and stir under reflux overnight under heating. Cool naturally after stirring, add methanol, H 2 O, carry out dispersion washing and filtration, obtain crude product. 2-(4-cyano-[1,1',4',1"]terphenyl-4"-yl)-5,6-bis was obtained by dispersing and washing the obtained crude product with acetone solvent 21.8 g (yield: 85%) of golden yellow (yamabuki color) powder of chloro-benzotriazole.

[0154] [chemical 13]

[0155]

[0156] For the obtained golden yellow powder, NMR was used to identify the structure.

[0157]...

Embodiment 3

[0166]

[0167] Charge 2-(4-cyano-[1,1',4',1"]terphenyl-4"-yl)-5,6-dichloro-benzotriazole in the reaction vessel: 5.0g, 1-Naphthylboronic acid: 6.2g, tris(dibenzylideneacetone) dipalladium (0): 0.5g, tricyclohexylphosphine: 0.6g, tripotassium phosphate: 14.4g, in 1,4-dioxane, H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, add H into the system 2 O, carry out dispersion washing and filtration, obtain crude product. 2-(4-Cyano-[1,1',4',1"]terphenyl-4"-yl) was obtained by crystallizing the obtained crude product with dichlorobenzene / acetone mixed solvent - 4.6 g (yield: 65%) of white powder of 5,6-di(naphthalen-1-yl)-benzotriazole (compound-44).

[0168] [chemical 15]

[0169]

[0170] For the obtained white powder, the structure was identified using NMR.

[0171] use 1 H-NMR (CDCl 3 ) detected the following 28 hydrogen signals.

[0172] δ(ppm)=8.58(2H), 8.14(2H), 7.94-7.73(13H), 7.60(3H), 7.46(2H), 7.28(3H), 7.11(1H), 7.01(2H)

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Abstract

The purpose of the present invention is: to provide, as a material for a highly efficient and highly durable organic EL element, an organic compound that has excellent characteristics such as excellent electron injection and transport performance, hole blocking ability, and high stability as a thin film; and to use the compound to provide a highly efficient and highly durable organic EL element. Given that benzotriazole ring structures, which have an affinity for electrons, have excellent heat resistance and have nitrogen atoms that can coordinate with metals, compounds that have a benzotriazole ring structure are designed and synthesized and used to evaluate the characteristics of organic EL elements, whereupon it is discovered that an organic EL element that had excellent characteristics could be obtained using a specifically structured compound that has a benzotriazole ring structure.

Description

technical field [0001] The present invention relates to compounds and devices suitable for organic electroluminescence devices (hereinafter simply referred to as organic EL devices) as self-luminous devices suitable for various display devices, and in particular, to compounds having a benzotriazole 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 Company developed a layered structure element that shared various functions with each material, thus making the organic EL element using organic materials 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/20C07D401/10C09K11/06H01L51/50
CPCC09K11/06C07D249/20C07D401/10C09K2211/1059H10K85/615H10K85/626H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/165H10K50/18H10K50/171H10K50/16H10K50/11C07D519/00H10K85/622H10K71/00H10K2101/10
Inventor 加濑幸喜林栽建金志泳平山雄太骏河和行
Owner HODOGOYA CHEMICAL CO LTD
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