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D-A-D conjugated molecule based on triphenylamine-thiophene imide, and preparation method and application thereof

A thiophene imide, D-A-D technology, applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., to achieve good thermal stability, good solubility, and good stability

Inactive Publication Date: 2012-12-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no literature or patent report on the application of thiophene imide small molecules in organic solar cells

Method used

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  • D-A-D conjugated molecule based on triphenylamine-thiophene imide, and preparation method and application thereof
  • D-A-D conjugated molecule based on triphenylamine-thiophene imide, and preparation method and application thereof
  • D-A-D conjugated molecule based on triphenylamine-thiophene imide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The synthetic route of conjugated molecule 1 is as follows:

[0051]

[0052] Take 65mg (0.13mmol) 1,3-dibromo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione, 230mg (0.4mmol) 4- (3-hexyl-5-(trimethyltin-yl)thiophen-2-yl)-N,N-diphenylaniline in a 25ml three-necked flask, add 5ml of freshly distilled anhydrous toluene, under the protection of nitrogen, stir After 30 minutes, add 20 mg (0.017 mmol) of tetrakis(triphenylphosphine) palladium, heat to 100 ° C, react for 2 days, add 10 ml of KF (5 g) aqueous solution and stir for 2 hours, pour the reaction mixture into water, and extract twice with dichloromethane , combined the organic layers, the obtained organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation to obtain a solid, and the mixed solvent of petroleum ether and dichloromethane in a volume ratio of 4:1 was used as eluent, silica gel ( 200-300 mesh) column chromatography to obtain 120 mg of orange-r...

Embodiment 2

[0055] The synthetic route of conjugated molecule 2 is as follows:

[0056]

[0057] Take 68mg (0.14mmol) of 1,3-dibromo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione, 176mg (0.36mmol) of N, N-diphenyl-4-(5-(trimethyltin)thiophen-2-yl)aniline was placed in a 25ml three-necked flask, 8ml of freshly distilled anhydrous toluene was added, under the protection of nitrogen, stirred for 30min, and four ( Triphenylphosphine)palladium 25mg (0.022mmol), nitrogen gas for 10min, heated to 110°C, reacted for 2 days, added 10ml KF (5g) aqueous solution and stirred for 2 hours, poured the reaction mixture into water, extracted twice with dichloromethane, Combine the organic layers, dry the obtained organic phase with anhydrous magnesium sulfate, filter, remove the solvent by rotary evaporation, use a mixed solvent of petroleum ether and dichloromethane with a volume ratio of 3:1 as eluent, silica gel (200-300 Mesh) column chromatographic separation and purification to obtain 90 mg of ...

Embodiment 3

[0060] The synthetic route of conjugated molecule 3 is as follows:

[0061]

[0062] Take 63mg (0.15mmol) 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione, 250mg (0.4mmol )4-(5-(tributyltin-based)thiophen-2-yl)-N,N-diphenylaniline in a 25ml three-necked flask, add 6ml of freshly distilled anhydrous toluene, under the protection of nitrogen, stir for 30min, add Tetrakis(triphenylphosphine)palladium 25mg (0.022mmol), nitrogen gas for 10min, heated to 110°C, reacted for 2 days, added 10ml KF (5g) aqueous solution and stirred for 2 hours, poured the reaction mixture into water, dichloromethane extracted two Once, the organic layers were combined, and the obtained organic phase was dried with anhydrous magnesium sulfate, filtered, and after the solvent was removed by rotary evaporation, the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 3:1 was used as eluent, silica gel (200 -300 mesh) column chromatography separation and purifica...

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Abstract

The invention relates to a D-A-D conjugated molecule based on triphenylamine as a donor (D) and thiophene imide as an acceptor (A), and a preparation method thereof, and an application of the molecule being used as a donor material for an active layer of organic photovoltaic cells (OPV). The D-A-D conjugated molecule based on triphenylamine-thiophene imide can be processed by a solution method, has relatively good sunlight-capturing capacity, hole-transporting capacity and heat stability, and is an ideal material for the OPV. The D-A-D conjugated molecule has the following general formula structure.

Description

technical field [0001] The present invention relates to a class of D-A-D conjugated molecules based on triphenylamine as a donor (D) and thiophene imide as an acceptor (A) and a preparation method thereof, and the use of such molecules as active layer donor materials in organic solar cells ( OPV) applications. Background technique [0002] Due to their good optical and electrical properties, organic semiconductor materials have become an important part of organic electronics research. Compared with traditional inorganic semiconductor devices, the devices made of them have the following advantages: low cost, flexibility, light weight , Can be prepared in a large area, etc. Based on these advantages, people have great interest in the research of organic electronics. In recent years, the research on organic solar cells (OPV) has developed very rapidly. In order to match the absorption spectrum of organic active layer materials with the solar emission spectrum and achieve high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L51/46
CPCY02E10/549
Inventor 占肖卫林禹泽程沛赵鑫刚刘瑶
Owner INST OF CHEM CHINESE ACAD OF SCI
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