2,1,3-benzothiadiazole derivative, and preparation method and application thereof

A technology for benzothiadiazole and derivatives, which is applied in the field of 2,1,3-benzothiadiazole derivatives and their preparation, can solve the problems of inconsistent relative molecular weight, unstable properties and the like, so as to improve the photoelectric conversion efficiency , high electron affinity, stable properties

Active Publication Date: 2015-06-17
邯郸市永年区维新蔬菜种植专业合作社
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polymer materials are not ideal enough for cathode interface modification materials, because polymer materials tend to have inconsistent rel

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 2,1,3-benzothiadiazole derivative, and preparation method and application thereof
  • 2,1,3-benzothiadiazole derivative, and preparation method and application thereof
  • 2,1,3-benzothiadiazole derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

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 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 reaction equat...

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Concentrationaaaaaaaaaa
Thicknessaaaaaaaaaa
Concentrationaaaaaaaaaa
Login to view more

Abstract

The embodiment of the invention provides a 2,1,3-benzothiadiazole derivative; in a chemical formula, R1 is an electron-rich substituent, one of R2 and R3 is an electron-deficient substituent and the other one of R2 and R3 is hydrogen atom, or R2 and R3 are both the electron-deficient substituents. The 2,1,3-benzothiadiazole derivative is good in electronic transmission performance and stable in material properties. In a second aspect, the embodiment of the invention provides a preparation method of the 2,1,3-benzothiadiazole derivative, the method is simple, and the prepared 2,1,3-benzothiadiazole derivative is good in electronic transmission performance. In a third aspect, the embodiment of the invention provides a cathode interfacial modification material; the cathode interfacial modification material is good in electron transport performance and stable in properties, and can improve the energy conversion efficiency of organic solar cells when used for the organic solar cells. In a fourth aspect, the embodiment of the invention provides the organic solar cells.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap