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Compound including benzimidazole ring structure and organic electroluminescent element

A technology of benzimidazole ring and compound, which is applied in the field of compounds with benzimidazole ring structure and organic electroluminescent elements, can solve the problems of insufficient film stability, low electron transport, and insufficient hole blocking function, etc. Improved luminous efficiency and driving voltage, low driving voltage, and excellent durability

Pending Publication Date: 2020-11-06
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, the low electron transport property is a major 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 (for example, refer to Non-Patent Document 5).
[0015] In addition, for bathocuproine (hereinafter referred to as BCP), although the work function is as high as 6.7eV and the hole blocking ability is high, the glass transition temperature (Tg) is as low as 83°C, so it lacks the stability of the film. , as a hole blocking layer, it cannot be said to function sufficiently
[0016] All materials have insufficient film stability or insufficient function of blocking holes

Method used

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  • Compound including benzimidazole ring structure and organic electroluminescent element
  • Compound including benzimidazole ring structure and organic electroluminescent element
  • Compound including benzimidazole ring structure and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143]

[0144] Put 2,4,6-tribromoaniline: 10.0g, 2-bromopyridine: 9.6g, potassium carbonate: 12.6g, copper powder: 0.2g, xylene: 100mL in the reaction vessel, and stir under reflux for 24 Hour. After stirring, it was naturally cooled, filtered and concentrated to obtain a crude product. Purification of the crude product by column chromatography (carrier: silica gel, eluent: dichloromethane / ethyl acetate) gave 6,8-dibromo-benzo[4,5]imidazo[1,2 -a] brown powder of pyridine: 5.9 g (60% yield).

[0145] [chemical 13]

[0146]

[0147] The structure of the obtained brown powder was identified using NMR.

[0148] use 1 H-NMR (DMSO-d 6 ) detected the following 6 hydrogen signals.

[0149] δ (ppm) = 9.11(1H), 8.72(1H), 7.92(1H), 7.77(1H), 7.67(1H), 7.11(1H).

[0150] Next, put 6,8-dibromo-benzo[4,5]imidazo[1,2-a]pyridine: 5.0g, 4-(pyridin-3-yl)phenylboronic acid: 6.7g, toluene: 50mL, ethanol: 10mL, then, add potassium carbonate: 6.4g dissolved in H 2 O: an aqueous solut...

Embodiment 2

[0157]

[0158] 6,8-dibromo-benzo[4,5]imidazo[1,2-a]pyridine: 5.0 g, 4-(naphthalene-1-yl)phenylboronic acid: 8.4 g, Toluene: 50mL, ethanol: 10mL, then, add potassium carbonate: 6.4g dissolved in H 2 O: an aqueous solution in 20 mL, and irradiated with ultrasonic waves for 30 minutes while blowing nitrogen gas. Add tetrakis(triphenylphosphine)palladium: 0.5 g to the nitrogen-filled solution, and stir under reflux for 24 hours. Cool naturally after stirring, add H 2 O, extraction and liquid separation were carried out, and the organic layer taken out was concentrated to obtain a crude product. Purification of the obtained crude product by column chromatography (carrier: silica gel, eluent: toluene / ethyl acetate) gave 6,8-bis{4-(naphthalen-1-yl-phenyl)}- Yellow powder of benzo[4,5]imidazo[1,2-a]pyridine (compound-21): 2.6 g (yield 30%).

[0159] [chemical 15]

[0160]

[0161] The structure of the obtained yellow powder was identified using NMR.

[0162] use 1 H-NMR (...

Embodiment 3

[0165]

[0166] Put 8-chloro-6-(4-pyridin-3-yl-phenyl)-benzo[4,5]imidazo[1,2-a]pyridine in the reaction vessel: 4.5g, 2-(9 , 9-diphenyl-9H-fluorene)-boronic acid: 5.5g, 1,4-dioxane: 80mL, then, add tripotassium phosphate: 8.1g dissolved in H 2 O: 20 mL of an aqueous solution was irradiated with ultrasonic waves for 30 minutes while passing nitrogen gas. Tris(dibenzylideneacetone)dipalladium (0): 0.3 g and tricyclohexylphosphine: 0.4 g were added to the nitrogen-passed solution, followed by stirring under reflux for 24 hours. After stirring, it was naturally cooled, and methanol was added to obtain a precipitated solid to obtain a crude product. The crude product was purified by recrystallization using 1,2-dichlorobenzene solvent to obtain 8-(9,9-diphenyl-9H-fluoren-2-yl)-6-(4-pyridin-3-yl Yellow powder of -phenyl)-benzo[4,5]imidazo[1,2-a]pyridine (compound-56): 3.7 g (yield 46%).

[0167] [chemical 16]

[0168]

[0169] The structure of the obtained yellow powder was ...

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Abstract

A compound including a benzimidazole ring structure, represented by general formula (1). (In formula (1), X1 and X2 may be the same or different and each represent a specific carbon atom or a nitrogenatom, Ar represents a specific group, R1 and R2 may be the same or different and each represent a specific group, and m is an integer of 0-4.)

Description

technical field [0001] The present invention relates to compounds and devices suitable for use in organic electroluminescence devices (hereinafter simply referred to as organic EL devices) as self-luminous devices suitable for various display devices. Specifically, it relates to compounds having a benzimidazole ring structure, An organic EL element containing this compound is used. 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 laminated structural 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 int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04H01L51/50
CPCC07D471/04C07D487/04H10K85/615H10K85/626H10K85/654H10K85/6572H10K50/165H10K50/18H10K50/171H10K50/16H10K50/11
Inventor 加濑幸喜李秀珍金是仁骏河和行平山雄太
Owner HODOGOYA CHEMICAL CO LTD