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Phenanthroimidazole compound substituted by diphenylphosphine oxide, preparation method and application thereof

A technology of diphenylphosphine and phenanthroimidazole, which is applied in the application field of organic light-emitting materials and optoelectronic devices, can solve the problems of not being able to have both good carrier transport balance and high blue light color purity, and achieve good current carrier The effect of sub-transport balance ability, high blue light color purity, and high fluorescence quantum efficiency

Pending Publication Date: 2021-01-08
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the defects and deficiencies that the organic electroluminescent device materials in the prior art cannot have both good carrier transport balance ability and high blue light color purity, and provide a diphenylphosphine substituted phenanthrene An imidazole compound, the organic electroluminescent device further prepared by using the compound can have both good carrier transport balance ability and high blue light color purity

Method used

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  • Phenanthroimidazole compound substituted by diphenylphosphine oxide, preparation method and application thereof
  • Phenanthroimidazole compound substituted by diphenylphosphine oxide, preparation method and application thereof
  • Phenanthroimidazole compound substituted by diphenylphosphine oxide, preparation method and application thereof

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Embodiment 1

[0045] A diphenylphosphine-substituted phenanthroimidazole compound has a molecular structure shown in formula (I):

[0046] Wherein R is a hydrogen atom or diphenylphosphine, when R is a hydrogen atom, it is named M1, and its molecular structure is:

[0047] When R is diphenylphosphine, it is named as M2, and its molecular structure is:

[0048] The preparation method of the phenanthroimidazoles substituted by the above-mentioned diphenylphosphine, comprising the steps of:

[0049] S1. Add 4-bromobenzaldehyde (1.86g, 10mmol), p-bromoaniline (1.70g, 10mmol), 9,10-phenanthrenequinone (2.08g, 10mmol), ammonium acetate (4.62g, 60mmol) into 100ml of In a two-necked flask (4-bromobenzaldehyde, bis-p-bromoaniline and 9,10-phenanthrenequinone in a molar ratio of 1:1:1), add 60ml of glacial acetic acid to obtain a dark brown suspension. After the mixture was stirred at 120° C. for 2 hours, the color of the solution changed from dark brown to black, and the reaction mixture was...

Embodiment 2

[0058] A diphenylphosphine-substituted phenanthroimidazole compound has a molecular structure shown in formula (I):

[0059] Wherein R is a hydrogen atom or diphenylphosphine, when R is a hydrogen atom, it is named M1, and its molecular structure is:

[0060] When R is diphenylphosphine, it is named as M2, and its molecular structure is:

[0061] The preparation method and separation steps of the above-mentioned diphenylphosphine-substituted phenanthrene imidazole compounds are the same as in Example 1, the difference is that the 4-bromobenzaldehyde, bis-p-bromoaniline and 9,10-phenanthrenequinone described in step S1 The molar ratio is replaced by 1:1:2.

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Abstract

The invention discloses a phenanthroimidazole compound substituted by diphenylphosphine oxide, a preparation method of the phenanthroimidazole compound and application of the phenanthroimidazole compound as an electroluminescent device. The phenanthroimidazole compound substituted by diphenylphosphine oxide has a molecular structure shown as formula (I) in the specification, wherein R is a hydrogen atom or diphenylphosphine oxide. The method includes: firstly utilizing 4-bromobenzaldehyde, di-p-bromoaniline, and 9, 10-phenanthrenequinone to prepare 4, 4-dibromo phenanthroimidazole; and then adding diphenylphosphine oxide, and carrying out nucleophilic substitution reaction to obtain the compound shown as the formula (I). The phenanthroimidazole compound substituted by diphenylphosphine oxide prepared by the invention has high blue light color purity and good carrier transport balance capability, and the solid film aggregation state high fluorescence quantum efficiency is high, so thatthe phenanthroimidazole compound substituted by diphenylphosphine oxide can be widely applied to organic light-emitting devices as a light-emitting material.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials and their application in optoelectronic devices, and more specifically, to a diphenylphosphine-substituted phenanthroimidazole compound and its preparation method and application. Background technique [0002] There have been many reports on the use of organic electroluminescent materials in small molecule organic electroluminescent devices, but most organic electroluminescent materials will form π-π stacking due to the planar structure of molecules in the aggregated state, resulting in the quenching of their fluorescence. reduce device efficiency. In order to improve device efficiency, traditional methods use groups to modify organic light-emitting materials. For example, Chinese patent CN110071220A discloses the application of a diphenylphosphine-modified benzimidazole material in OLEDs, but the electron transport of the molecule itself The performance is average, which le...

Claims

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Application Information

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IPC IPC(8): C07F9/6506C09K11/06H01L51/54H01L51/50
CPCC07F9/65068C09K11/06C09K2211/1014C09K2211/1044H10K85/6572H10K50/11
Inventor 陈思维霍延平黄酬陈涛邱志鹏籍少敏
Owner GUANGDONG UNIV OF TECH
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