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Compound containing triazine group and application of compound as three-dimensional electron acceptor material

A technology of electron acceptor materials and triazine groups, which is applied in the field of three-dimensional electron acceptor materials and compounds containing bitriazine groups, can solve the problems of energy conversion efficiency to be improved and achieve good commercial application prospects , Avoid the effect of too strong aggregation and small space hindrance

Active Publication Date: 2021-08-10
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the energy conversion efficiency of organic photovoltaic devices based on such electronic materials still needs to be improved, and it is urgent to develop new and efficient electron acceptor materials.

Method used

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  • Compound containing triazine group and application of compound as three-dimensional electron acceptor material
  • Compound containing triazine group and application of compound as three-dimensional electron acceptor material
  • Compound containing triazine group and application of compound as three-dimensional electron acceptor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A compound containing triazine group, its preparation method is as follows:

[0028] 1) Add compound 1 (2eq), cyanuric chloride (1eq), tetrakistriphenylphosphine palladium catalyst (0.05eq) and cuprous iodide (0.1eq) into the reaction flask, pump out nitrogen, and inject oxygen-free carbonic acid Potassium aqueous solution (2mol / L) and appropriate amount of toluene were reacted overnight at 80°C, the product was washed with water and extracted three times with dichloromethane, the organic phases were combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation, and dichloromethane was used as eluent Silica gel column chromatography was carried out to obtain product 2 with a yield of 65%;

[0029] The reaction formula is as follows:

[0030]

[0031] 2) Compound 2 was dissolved in DMF, 2 times the molar amount of reduced copper powder was added, heated to reflux overnight, and the final product 3 was obtained by silica gel column c...

Embodiment 2

[0035] A compound containing triazine group, its preparation method is as follows:

[0036] 1) Add compound 4 (2eq), cyanuric chloride (1eq), tetrakistriphenylphosphine palladium catalyst (0.05eq) and cuprous iodide (0.1eq) into the reaction flask, exhaust nitrogen, inject oxygen-free carbonic acid Potassium aqueous solution (2mol / L) and appropriate amount of toluene were reacted overnight at 80°C, the product was washed with water and extracted three times with dichloromethane, the organic phases were combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation, and dichloromethane was used as eluent Silica gel column chromatography was carried out to obtain product 5 with a yield of 75%;

[0037] The reaction formula is as follows:

[0038]

[0039] 2) Compound 5 was dissolved in DMF, 2 times the molar amount of reduced copper powder was added, heated to reflux overnight, and the final product 6 was obtained by silica gel column chroma...

Embodiment 3

[0043] A compound containing triazine group, its preparation method is as follows:

[0044] 1) Add compound 7 (2eq), cyanuric chloride (1eq), tetrakistriphenylphosphine palladium catalyst (0.05eq), cuprous iodide (0.05eq) into the reaction flask, pump out nitrogen, inject anaerobic anaerobic Water toluene and DMF appropriate amount, reflux reaction for 24h, the product was washed with water and extracted three times with dichloromethane, the organic phase was combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation, and silica gel column chromatography was separated with dichloromethane as eluent , to obtain product 5 with a yield of 75%;

[0045]

[0046] The reaction formula is as follows:

[0047] 2) Compound 8 was dissolved in DMF, 2 times the molar amount of reduced copper powder was added, heated to reflux overnight, and the final product 9 was obtained by silica gel column chromatography with a yield of 80%.

[0048] The reac...

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Abstract

The invention relates to a compound containing a triazine group and application of the compound as a three-dimensional electron acceptor material, the structural formula of the compound containing the triazine group is shown in the specification, wherein EW is selected from naphthalene diimide derivatives and perylene diimide derivatives. When the triazine group-containing compound provided by the invention is used as an electron acceptor material, the photoelectric conversion efficiency of a solar cell can be remarkably improved, and the triazine group-containing compound has a good commercial application prospect.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds containing three or more heterocyclic rings, and relates to a class of compounds containing bitriazine groups and their application as three-dimensional electron acceptor materials. Background technique [0002] The development and utilization of solar energy is expected to become a solution to energy and environmental problems faced by the world. It is a feasible way to develop photovoltaic technology and realize the commercialization of solar cells. At present, inorganic solar cells have disadvantages such as unenvironmental protection, high energy consumption, and long energy repayment time in the preparation process, while organic photovoltaics with abundant material sources and solution processability have great potential, which is particularly eye-catching. [0003] The active layer of organic photovoltaic materials is usually made of a blend film of electron donor material (p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46H01L51/42
CPCC07D519/00H10K85/621H10K85/654H10K85/657H10K85/6572H10K30/65H10K30/00Y02E10/549
Inventor 高翔孙逢博王一诺张林骅刘治田
Owner WUHAN INSTITUTE OF TECHNOLOGY
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