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Application of quinolone derivatives as OLED emission materials in organic electroluminescent devices

A technology for electroluminescent devices and emitting materials, which is applied in the application of luminescent materials, electro-solid devices, gas discharge lamps, etc., and can solve the problem of low fluorescence quantum efficiency and so on.

Inactive Publication Date: 2011-11-30
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the position of the emission peak of quinolone derivatives is biased towards the ultraviolet and the fluorescence quantum efficiency is not high, there has been no report on using them as OLED emission materials.

Method used

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  • Application of quinolone derivatives as OLED emission materials in organic electroluminescent devices
  • Application of quinolone derivatives as OLED emission materials in organic electroluminescent devices
  • Application of quinolone derivatives as OLED emission materials in organic electroluminescent devices

Examples

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Effect test

Embodiment 1

[0073] Embodiment 1,1-methyl-3, the preparation of 4-diphenylquinolin-2 (1H)-ketone (Q1)

[0074]

[0075] The first step: take 1-methyl-4-phenylquinolin-2(1H)-one with a molar ratio of 1:1, and N-bromosuccinimide as raw materials, and dissolve the above-mentioned raw materials in N, N-dimethylformamide was reacted with stirring at room temperature for 10 hours, and a large amount of solid was precipitated by adding water, which was washed and dried to obtain the corresponding bromide with a yield of 80%.

[0076] The second step: under the protection of nitrogen, the bromide obtained in the first step and phenylboronic acid (molar ratio is 1: 1) are dropped into two-necked flasks, and a catalytic amount of tetrakis (triphenyl) phosphine palladium) and mixed solvent ( Sodium carbonate solution (2mol / L):toluene:ethanol=1:4:4), keep the temperature at 90-100°C, stir for 24 hours, extract with ether, and the product is subjected to column chromatography (eluent is petroleum et...

Embodiment 2

[0087] Embodiment 2, the preparation of 1-methyl-3-(2-naphthyl)-4-phenylquinolin-2(1H)-one (Q2)

[0088]

[0089] The first step: take 1-ethyl-4-phenylquinolin-2(1H)-one with a molar ratio of 1:1, and N-bromosuccinimide as raw materials, dissolve the above raw materials in N, N-dimethylformamide was stirred at room temperature for 10 hours, and a large amount of solid was precipitated by adding water. The solid was washed and dried to obtain the corresponding bromide with a yield of 80%.

[0090]The second step: under the protection of nitrogen, put the product obtained in the first step and 2-naphthylboronic acid (the molar ratio is 1:1) into a two-neck flask, add a catalytic amount of tetrakis (triphenyl) phosphine palladium) and a mixed solvent (sodium carbonate solution (2mol / L):toluene:ethanol=1:4:4), keep the temperature at 90-100°C, stir for 24 hours, extract with ether, and the product is subjected to column chromatography (eluent is petroleum ether / ethyl acetate E...

Embodiment 3

[0100] Embodiment 3, the preparation of 1-methyl-3-(4-(9-carbazolyl)phenyl)-4-phenylquinolin-2(1H)-one (Q3)

[0101]

[0102] The first step: take 1-methyl-4-phenylquinolin-2(1H)-one with a molar ratio of 1:1, and N-bromosuccinimide as raw materials, and dissolve the above-mentioned raw materials in N, N-dimethylformamide was stirred at room temperature for 10 hours, and a large amount of solid was precipitated by adding water. The solid was washed and dried to obtain the corresponding bromide with a yield of 80%.

[0103] The second step: under the protection of nitrogen, put the product obtained in the first step and 4-(9-carbazolyl)phenylboronic acid (1:1 in molar ratio) into a two-necked bottle, and add a catalytic amount of tetrakis(triphenyl) ) phosphine palladium) and mixed solvent (sodium carbonate solution: toluene: ethanol = 1: 4: 4), keep the temperature at 90-100 ° C, stir for 24 hours, extract with ether, and the product is subjected to column chromatography (e...

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Abstract

The invention discloses the application of quinolone derivatives represented by formula I as emission materials in the preparation of organic electroluminescent devices, especially the application in the preparation of white light organic electroluminescent devices. The general structural formula of the compound is shown in Formula I. This type of compound is used as an emission material for an organic light-emitting layer of an organic electroluminescent device, and further relates to an organic electroluminescent device comprising a light-emitting layer, the light-emitting layer containing at least one quinolone derivative shown in formula I as an emission material, and containing a quinolone Derivatives or an electron transport layer composed of them, a hole blocking layer containing quinolone derivatives or composed of them; and a device comprising the organic electroluminescent device of the present invention. The quinolone derivatives provided by the present invention have suitable triplet energy levels, and the energy utilization is significantly improved. When used in the preparation of organic electroluminescent devices, the manufactured devices are obtained in terms of brightness, current density and efficiency at high current densities. a satisfactory result. Formula I

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and specifically relates to the use of quinolone derivatives as emission materials in the preparation of organic electroluminescent devices. Background technique [0002] In recent years, the research on white light organic electroluminescent materials and devices has received great attention from international academic circles, governments and industries. Countries and regions such as the United States, Europe, Japan, etc. have launched major research programs (NextGeneration Lighting Initiative in the United States, OLLA in the European Union). , Japan 21Century Lighting Program) to strengthen research in this field, the reasons are: First, white organic electroluminescent technology (WOLED), together with inorganic LED technology, may be one of the most important solid-state light source technologies in the new generation. According to statistics, 20% of the average electric...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/54C07D215/227C07D401/10C07D401/14C07D215/38
CPCY02B20/181Y02B20/00
Inventor 张晓宏黄达郑才俊叶俊欧雪梅
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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