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A kind of 2,1,3-benzothiadiazole derivative and its preparation method and application

A technology of benzothiadiazole and its derivatives, which is applied in the field of 2,1,3-benzothiadiazole derivatives and its preparation, can solve problems such as inconsistent relative molecular weight and unstable properties, and achieve improved photoelectric conversion efficiency , high electron affinity, stable properties

Active Publication Date: 2017-11-17
邯郸市永年区维新蔬菜种植专业合作社
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, polymer materials are not ideal enough for cathode interface modification materials, because polymer materials tend to have inconsistent relative molecular weights due to different degrees of polymerization during the preparation process, which will lead to unstable properties during use.

Method used

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  • A kind of 2,1,3-benzothiadiazole derivative and its preparation method and application
  • A kind of 2,1,3-benzothiadiazole derivative and its preparation method and application
  • A kind of 2,1,3-benzothiadiazole derivative and its preparation method and application

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preparation example Construction

[0056] In the second aspect, the embodiment of the present invention provides a preparation method of 2,1,3-benzothiadiazole derivatives, comprising the following steps:

[0057] Provide chemical structural formulas such as the compound shown in formula A and the compound shown in formula B respectively,

[0058] A: B:

[0059] Among them, R 1 is an electron-rich substituent, R 2 and R 3 where one is an electron deficient substituent and the other is a hydrogen atom, or R 2 and R 3 Both of them are electron deficient substituents;

[0060] In an oxygen-free environment, the compound shown in formula A and the compound shown in formula B with a molar ratio of 1:1 to 1:10 are added into an organic solvent containing a catalyst for dissolution to obtain a mixed solution, and the The above mixed solution is subjected to Knaevengel condensation reaction at 40°C to 150°C, and the reaction time is 4 to 48 hours to obtain the product, and the organic solvent is acetonitrile,...

Embodiment 1

[0129] A preparation method of 2,1,3-benzothiadiazole derivatives, comprising the following steps:

[0130] 4-formyl-7-dimethylaminobenzothiadiazole with chemical structural formula shown in formula A1 and cyanoacetoxypropyl ester shown in formula a1 are dissolved in acetonitrile containing catalyst piperidine in equimolar ratio , to obtain a mixed solution, the concentration of 4-formyl-7-dimethylaminobenzothiadiazole in the mixed solution is 20mg / ml, and the molar weight of piperidine is 4-formyl-7-dimethylaminobenzothiadiazole 2% of the molar amount of oxadiazole; under the state of nitrogen protection, the mixed solution was stirred at 80°C, and the 4-formyl-7-dimethylaminobenzothiadiazole and cyanoacetate alkyl ester in the mixed solution produced croven The product was obtained by the Gehl condensation reaction with a reaction time of 4 hours. The product is purified by silica gel column chromatography to obtain 2,1,3-benzothiadiazole derivatives shown in Ia1, and the r...

Embodiment 2

[0137] A preparation method of 2,1,3-benzothiadiazole derivatives, comprising the following steps:

[0138] Dissolve 4-formyl-7-dimethylaminobenzothiadiazole with chemical structural formula as shown in formula A1 and cyanoacetate hexyl ester with chemical structural formula as shown in formula a2 in a molar ratio of 1:10 in a catalyst containing alkaline In the toluene of aluminum oxide, a mixed solution is obtained, the concentration of 4-formyl-7-dimethylaminobenzothiadiazole in the mixed solution is 50 mg / ml, and the molar weight of basic aluminum oxide is 4- 10% of the molar weight of aldehyde-7-dimethylaminobenzothiadiazole; under the state of nitrogen protection, the mixed solution was stirred at 40°C, and the 4-aldehyde-7-dimethylaminobenzothiadiazole in the mixed solution The product was obtained by Knaveningel condensation reaction with alkyl cyanoacetate, and the reaction time was 24 hours. The product is purified by silica gel column chromatography to obtain 2,1,3...

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Abstract

An embodiment of the present invention provides a 2,1,3-benzothiadiazole derivative; in its chemical formula, R1 is an electron-rich substituent, one of R2 and R3 is an electron-deficient substituent and the other is a hydrogen atom, or Both of R2 and R3 are electron deficient substituents. The 2,1,3-benzothiadiazole derivative has good electron transport performance and stable material properties. The second aspect of the embodiment of the present invention provides a method for preparing 2,1,3-benzothiadiazole derivatives, the method is simple, and the prepared 2,1,3-benzothiadiazole derivatives transport electrons Good performance. The third aspect of the embodiments of the present invention provides a cathode interface modification material. The cathode interface modification material has good electron transport performance and stable properties. When used in an organic solar cell, the energy conversion efficiency of the organic solar cell can be improved. The fourth aspect of the embodiment of the present invention provides an organic solar cell.

Description

technical field [0001] The invention relates to the field of organic materials, in particular to a 2,1,3-benzothiadiazole derivative and its preparation method and application. Background technique [0002] Compared with traditional inorganic solar cells, organic solar cells can be prepared on flexible substrates, which have the advantages of flexibility, lightness, unbreakability and simple production process, and have attracted more and more attention. However, the energy conversion efficiency of organic solar cells is low. The main reason is that the charge transport performance of the active layer material in organic solar cells is poor, so that the electrons and holes generated after organic solar cells absorb light energy cannot form effective currents. Instead, after recombination, it is converted into heat and other energy and is wasted. In order to better transport electrons and holes, more and more researchers have begun to focus on the research of electrode inter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/14C07D417/06H01L51/46
CPCC07D285/14C07D417/06H10K85/657H10K30/00H10K30/80Y02E10/549
Inventor 李慧夏圣安谢封超
Owner 邯郸市永年区维新蔬菜种植专业合作社
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