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d-a polymer photovoltaic materials based on thienoisobenzopyran asymmetric electron-donating unit and its application

A benzopyran, photovoltaic material technology, applied in photovoltaic power generation, electrical components, circuits and other directions, can solve the problems of complex preparation process and few varieties of high-efficiency photoelectric conversion devices, so as to improve the charge migration effect and enhance the dipole moment effect. , the effect of improving the mobility

Active Publication Date: 2019-02-15
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] Aiming at the current shortage of polymer photovoltaic materials with excellent performance and the complicated preparation process of high-efficiency photoelectric conversion devices, a new type of thiophene[3,2-c]isobenzopyran containing oxygen heteroatoms was invented. Symmetric push electron (D) unit and its D-A type polymer photovoltaic material

Method used

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  • d-a polymer photovoltaic materials based on thienoisobenzopyran asymmetric electron-donating unit and its application
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  • d-a polymer photovoltaic materials based on thienoisobenzopyran asymmetric electron-donating unit and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Bistin-substituted 5,5-bis(dodecyl)-7-(2-(thienyl)-5-hydro-thiophene[3,2-c]isochromene polymer monomer (M1 ), the synthesis route is shown in the figure below.

[0058]

[0059] 1.1 Synthesis of 2-(tributyltin)-3-methoxythiophene

[0060] In a 250mL three-necked flask, dissolve 3-methoxythiophene (4.56g, 40mmol) in 80mL dry tetrahydrofuran, stir magnetically, and slowly add n-butyllithium (27.5mL, 1.6M) dropwise at -78°C, - React at 78°C for 0.5h, and at room temperature for 2h. Then tributyltin chloride (14.3g, 44mmol) was added dropwise at -78°C, and reacted at room temperature for 5h. The reaction solution was poured into 100 mL of water, extracted three times with petroleum ether, 30 mL each time, and the combined organic layer was washed with saturated brine three times, 50 mL each time. The organic layer was dried, the organic solvent was distilled off under reduced pressure, and dried in vacuo to obtain a pale yellow liquid (15.5 g, 98.0%). 1 H NMR (400MHz...

Embodiment 2

[0074]

[0075] Synthesis of Polymer PTCBT

[0076] In a 25mL two-necked bottle, add dialkyltin-substituted polymerized monomer M1 (243mg, 0.205mmol), 4,7-dibromo-2,1,3-benzothiadiazole (58mg, 0.2mmol), three (Dibenzylideneacetone) dipalladium (5mg), tris(o-tolyl)phosphine (10mg), oxygen-free toluene 6mL. Under the protection of nitrogen flow, the temperature was controlled at 110° C. for 24 h. Bromobenzene (0.2 mL) was injected into the syringe as a capping agent, and reacted at 110° C. for 2 h. Cool naturally, add 10mL toluene to dilute the reaction solution, add dropwise to 100mL methanol for sedimentation, filter with suction, dissolve the solid in chlorobenzene, quickly separate through a silica gel column, and settle with methanol. The collected solids were sequentially subjected to Soxhlet extraction with methanol, diethyl ether and chloroform, and the chloroform extract was concentrated, dropped into methanol to settle. The solid was collected by suction filtrati...

Embodiment 3

[0077] The synthesis of embodiment 3 polymer PTCFBT

[0078]

[0079] In a 25mL two-necked bottle, add dialkyltin-substituted polymerized monomer M1 (243mg, 0.205mmol), 4,7-dibromo-5-fluoro-2,1,3-benzothiadiazole (58mg, 0.2 mmol), tris(dibenzylideneacetone) dipalladium (5mg), tris(o-tolyl)phosphorus (10mg), oxygen-free toluene 6mL. Under the protection of nitrogen flow, the temperature was controlled at 110° C. for 24 h. Bromobenzene (0.2 mL) was injected into the syringe as a capping agent, and reacted at 110° C. for 2 h. Cool naturally, add 10mL toluene to dilute the reaction solution, add dropwise to 100mL methanol for sedimentation, filter with suction, dissolve the solid in chlorobenzene, quickly separate through a silica gel column, and settle with methanol. The collected solids were sequentially subjected to Soxhlet extraction with methanol, diethyl ether and chloroform, and the chloroform extract was concentrated, dropped into methanol to settle. The solid was co...

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Abstract

The invention relates to the synthesis of a class of D-A polymer photovoltaic materials based on thienoisobenzopyran asymmetric donor units, and their application in polymer photovoltaic devices. Among them, the electron-pushing (D) unit of the D‑A polymer material is a thienoisobenzopyran derivative, and the electron-accepting (A) unit is benzothiadiazole and its fluorinated derivatives. Such polymers can be widely used as donor materials for high-efficiency solution-processed polymer solar cells. When the acceptor material of the device is fullerene, the maximum energy conversion efficiency and open circuit voltage of the bulk heterojunction polymer solar cell are as high as 8.96% and 0.85V, respectively. The invention realizes the high-efficiency energy conversion of the asymmetric donor unit polymer photovoltaic material in the polymer solar cell.

Description

technical field [0001] The invention relates to the field of organic polymer solar cells, in particular to the synthesis of a type of D-A polymer photovoltaic material based on thiophene[3,2-c]isobenzopyran asymmetric electron donating unit and its application in polymer solar cells. battery applications. technical background [0002] Under the dual constraints of the increasing scarcity of fossil energy and the urgent need to protect the environment, energy and environmental issues have become the key and difficult issues that need to be solved urgently in the world. Due to the incomparable advantages of solar energy, which is inexhaustible, safe, pollution-free, and without geographical restrictions, the development and application of solar energy has become a hot spot in the research of global green new energy. Among them, the solar cell technology that converts solar energy into electrical energy is a key research direction in the development and application of solar en...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/122C08G61/123C08G61/126C08G2261/3246C08G2261/91C08G2261/414C08G2261/18C08G2261/1412C08G2261/146C08G2261/124C08G2261/3223C08G2261/3243H10K85/151H10K30/00Y02E10/549
Inventor 朱卫国陶强张俊谭华王亚飞朱梦冰
Owner CHANGZHOU UNIV