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Cyano-modified pyridino imidazole derivative as well as preparation method and application thereof

A technology for pyridoimidazoles and derivatives, which is applied in the fields of organic chemistry, chemical instruments and methods, organic chemistry, etc., can solve the problems of low fluorescence quantum yield and poor solubility, and achieve high fluorescence quantum yield, Good solubility and the effect of suppressing exciton annihilation

Active Publication Date: 2020-11-03
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved in the present invention is to overcome the defects and deficiencies of the existing pyridoimidazole derivative light-emitting materials, such as low fluorescence quantum yield and poor solubility, and provide a cyano-modified pyridoimidazole derivative, which High fluorescence quantum yield, can produce aggregation-induced emission (AIE) effect, can emit red light, and has good thermal stability and solubility

Method used

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  • Cyano-modified pyridino imidazole derivative as well as preparation method and application thereof
  • Cyano-modified pyridino imidazole derivative as well as preparation method and application thereof
  • Cyano-modified pyridino imidazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] A cyano-modified pyridoimidazole derivative, named Ben-CN, has the following molecular structure:

[0072]

[0073] The preparation method of the above-mentioned Ben-CN comprises the following steps:

[0074] Weigh 150 mg of (E)-4-(3-(4-bromophenylhydrazine))benzonitrile, 80 mg of 2-aminopyridine, 60 mg of iodine, and 3 mL of dichloroethane in a 10 mL sealed tube, and perform a Michael ring at 120°C. Combined reaction, after processing, (4-(2-(4-bromobenzene) imidazo[1,a])pyridin-3-yl)benzonitrile is obtained; DCE is dichloroethane;

[0075] Its reaction equation is:

[0076]

[0077] Weigh 180 mg of (4-(2-(4-bromobenzene) imidazo[1,a]) pyridin-3-yl) benzonitrile, 115 mg of 10-hydrogen-phenoxazine, and 80 mg of potassium tert-butoxide prepared above , 4 mg of tri-tert-butylphosphine, 5.5 mg of palladium acetate and 5 mL of toluene in a sealed tube, stirred to remove the air in the device and filled with nitrogen protection, heated and stirred under reflux at 130...

Embodiment 2

[0081] A cyano-modified pyridoimidazole derivative, named Bd-CN, has the following molecular structure:

[0082]

[0083] The preparation method of the above-mentioned Bd-CN is the same as in Example 1, the difference is that (E)-4-(3-(4-bromophenylhydrazine))benzonitrile is replaced by (E)-4-(3-(4- Bromophenylhydrazine)) nitrile, 2-aminopyridine was replaced by 2-amino-4-cyano-pyridine to obtain (4-(2-(4-bromophenyl)imidazo[1,a])pyridin-3-yl ) pyridinenitrile;

[0084] Its reaction equation is as follows:

[0085]

Embodiment 3

[0087] A cyano-modified pyridoimidazole derivative with the following molecular structure:

[0088]

[0089] The preparation method of the above-mentioned cyano-modified pyridoimidazole derivatives is the same as that of Example 1, the difference is that (4-(2-(4-bromobenzene)imidazo[1,a])pyridin-3-yl)benzyl The nitrile was replaced by (4-(2-(4-bromophenyl)imidazo[l,a])pyridin-3-yl)benzyl-pyridinenitrile.

[0090] Its reaction equation is as follows:

[0091]

[0092]

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Abstract

The invention discloses a cyano-modified pyridino-imidazole derivative as well as a preparation method and application thereof, wherein the cyano-modified pyridino-imidazole derivative has a molecularstructure as shown in a formula (I); in the formula, R1 is hydrogen or cyano, R2 is hydrogen or cyano, and R1 and R2 are not hydrogen at the same time. According to the invention, C-H-Pi stacking structures and cyano groups are introduced into the pyridino imidazole derivatives to obtain higher fluorescence quantum yield, and enhanced electron withdrawing capacity of acceptor groups and spectralred shift; in addition, the derivatives also have better AIE effect, efficient TADF (thermally activated delayed fluorescence) property, good thermal stability and solubility. Therefore, the materialcan be used as a red light emitting material, a light emitting device or an intelligent light emitting material, and can be applied to the fields of full-color display and solid-state lighting.

Description

technical field [0001] The present invention relates to the technical field of organic light-emitting materials, and more specifically, to a cyano-modified pyridimidazole derivative and a preparation method and application thereof. Background technique [0002] The technology of organic light-emitting materials used as organic light-emitting diodes (OLEDs) is widely used in flat panel displays, smart phones, and solid-state lighting. Significant advantages such as fast response speed and flexibility. [0003] However, the red light-emitting materials in the current organic light-emitting materials will greatly enhance the non-radiative transition rate of molecules due to their inherent narrow bandgap, resulting in a large energy loss. Therefore, the solid-state fluorescence quantum yield is not high, thermal stability and solubility problems. [0004] For example, Chinese patent CN102070632B discloses a pyridoimidazole derivative and its application in organic electrolumin...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C07B2200/13C09K2211/1007C09K2211/1044
Inventor 霍延平邱志鹏黄酬付裕陈文铖籍少敏
Owner GUANGDONG UNIV OF TECH
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