Pyridine-quinoline derivative, preparation method and organic light-emitting device

A technology of quinolines and derivatives, which is applied in the field of organic optoelectronic materials, can solve the problems of single species and difficult performance optimization, and achieve the effect of low manufacturing cost and reduced manufacturing cost

Inactive Publication Date: 2016-05-11
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to provide a simple and easy-to-obtain diarylpyridoquinoline electron transport material for overcoming the problem that the electron transport materials in organic electroluminescent devices are single and difficult to optimize in the prior art.

Method used

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  • Pyridine-quinoline derivative, preparation method and organic light-emitting device
  • Pyridine-quinoline derivative, preparation method and organic light-emitting device
  • Pyridine-quinoline derivative, preparation method and organic light-emitting device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Add 100mmol of 4,9-dichloropyrido[2,3-g]quinoline and 220mmol of 4-(N,N-diphenyl)aminophenylboronic acid into a 1L three-necked flask, dissolve in 400mL of toluene, and Under the protection of nitrogen, add tetrakistriphenylphosphine palladium 1.5mmol, potassium carbonate 250mmol, distilled water 100mL, stir and reflux for 16 hours, cool to room temperature after the reaction, separate liquid, pass through a silica gel funnel, wash, spin dry, recrystallize, filter, 77 mmol of white solid compound 1 was obtained, yield 77%.

[0037] Embodiment 2: the synthesis of compound 2

Embodiment 2

[0038]

[0039] Add 100mmol of 4,9-dichloropyrido[2,3-g]quinoline and 220mmol of 1-naphthaleneboronic acid into a 1L three-necked flask, dissolve in 400mL of toluene, and add tetrakistriphenylphosphine palladium under nitrogen protection 1.5mmol, potassium carbonate 250mmol, distilled water 100mL, stirred and refluxed for 16 hours, cooled to room temperature after the reaction, separated, passed through a silica gel funnel, washed, spin-dried, recrystallized, filtered to obtain 87mmol of white solid compound 2, yield 87%.

[0040] Embodiment 3: the synthesis of compound 3

Embodiment 3

[0041]

[0042] Add 100mmol of 4,9-dichloropyrido[2,3-g]quinoline and 220mmol of 9-phenanthrene boronic acid into a 1L three-neck flask, dissolve in 400mL of toluene, and add tetrakistriphenylphosphine palladium under nitrogen protection 1.5mmol, potassium carbonate 250mmol, distilled water 100mL, stirred and refluxed for 16 hours, cooled to room temperature after the reaction, separated, passed through a silica gel funnel, washed, spin-dried, recrystallized, filtered to obtain 79mmol of white solid compound 3, yield 79%.

[0043] Embodiment 4: the synthesis of compound 4

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PUM

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Abstract

The invention relates to a pyridine-quinoline compound, a preparation method thereof and an organic light-emitting device made from the compound. The pyridine-quinoline derivative is obtained by connection with boronic acid derivatives with different substituting groups on the basis of difluoropyridine-[2,3-g]quinoline; the preparation process is simple, the reaction condition is mild, the pyridine-quinoline derivative can be taken as an electron transport material to be applied to organic light-emitting devices. According to the pyridine-quinoline derivative, the preparation method and the organic light-emitting device, the prepared pyridine-quinoline compound is high in efficiency, high in brightness, long in service life, better in charge transfer capacity and high in glass transition temperature and non-crystallizable when applied to organic light-emitting devices.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a class of pyridoquinoline-containing derivatives, a preparation method and an organic light-emitting device. Background technique [0002] Organic electroluminescent device (OLED) is a new type of flat display device, which has the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, long life, light weight and thin thickness. Due to the rapid development of optoelectronic communication and multimedia fields in recent years, organic optoelectronic materials have become the core of information and electronic industries in modern society. [0003] An organic electroluminescent device generally includes an anode, an organic light-emitting layer, and a cathode. In the organic light-emitting layer, the electrons of the cathode and the holes of the anode recombine to form excitons, and when the excitons become...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
Inventor 马晓宇宋巧红彭勃李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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