Synthesis and application of (D-A)n+1D type oligomer photovoltaic donor material based on benzodithiophene-4,8-dione

A technology of dithiophene and photovoltaic materials, which is applied in the application field of oligomer solar cell devices, can solve the problems of unclear molecular structure and performance, insufficient manifestation of advantages, and low energy conversion efficiency of devices, so as to achieve high-efficiency energy conversion Efficiency, high molar absorptivity, and the effect of improving short-circuit current

Inactive Publication Date: 2018-07-06
CHANGZHOU UNIV
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Problems solved by technology

[0018] At present, there are few literature reports on oligomer photovoltaic materials with D-A block units. The advantages of oligomers taking into account the advantages of polymers and organic small molecule photovoltaic materials are not fully reflected. The relationship between molecular structure and performance is not yet clear. The energy conversion efficiency of devices Low and other problems, we invented a class with (D-A) n+1 Oligomer photovoltaic donor material with D(n=1,2...) structure, the molecular structure of this type of oligomer is characterized by using benzodithiophenedione (BDD) as the electron acceptor (A ) units, thiophene, benzene, benzodithiophene derivatives are electron donor (D) units

Method used

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  • Synthesis and application of (D-A)n+1D type oligomer photovoltaic donor material based on benzodithiophene-4,8-dione
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  • Synthesis and application of (D-A)n+1D type oligomer photovoltaic donor material based on benzodithiophene-4,8-dione

Examples

Experimental program
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Embodiment 1

[0061] Synthesis of 4,8-dibromo-bis(2-ethylhexyl)benzo[1,2-c:4,5-c']dithiophene-4,8-dione (M1)

[0062]

[0063] 1.1 Synthesis of 2,5-dibromo-3,4-dicarboxythiophene

[0064] Add 3,4-dicarboxythiophene (5g, 29.04mmol) and 40mL glacial acetic acid into a 100mL one-necked flask in turn, stir at room temperature, add liquid bromine (8.9mL, 174.24mol) into a 25mL constant pressure dropping funnel, Slowly drop into the reaction flask, react for 12h. After the reaction was finished, the reaction solution was poured into 500mL saturated sodium bisulfate solution and stirred until a beige solid was precipitated, filtered under reduced pressure, and dried to obtain a beige solid (8.2g, 85.6%), the chemical formula was C 6 h 2 Br 2 o 4 S, MS m / z: [M1] 329.8.

[0065] 1.2 Synthesis of 2,5-dibromo-3,4-diacylchlorothiophene

[0066] Add 2,5-dibromo-3,4-dicarboxythiophene (2g, 6.06mol) and 50mL of dry dichloromethane into a 100mL one-necked flask in turn, stir at room temperature, a...

Embodiment 2

[0070] 4,8-bis-(5-bromothienyl)-bis(2-ethylhexyl)benzo[1,2-c:4,5-c′]dithiophene-4,8-dione (M2) Synthesis

[0071]

[0072] 2.1 Synthesis of 4,8-dithienyl-bis(2-ethylhexyl)benzo[1,2-c:4,5-c′]dithiophene-4,8-dione

[0073] Add M1 (0.5g, 0.83mmol), tributylstannylthiophene (0.93g, 2.5mmol), tetrakis(triphenylphosphine)palladium (96mg), and 30mL toluene into a 100mL two-necked flask in turn, and nitrogen deoxidation . The temperature was raised and transferred to 110° C. and the reaction was stirred for 12 h. The reaction was stopped, and after the reactant was cooled to room temperature, it was poured into 100 mL of distilled water and extracted with dichloromethane (3 x 30 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent, and the residue was subjected to column chromatography with petroleum:dichloromethane mixed solution (v / v, 5:1) as eluent After separation...

Embodiment 3

[0077] Synthesis of 2-trimethyltin-4,8-bis(5-(2-ethylhexyl)thienyl)benzo[1,2-b:4,5-b']dithiophene (M3)

[0078]

[0079] 4,8-bis(5-(2-ethylhexyl)thienyl)benzo[1,2-b:4,5-b']dithiophene (0.3g, 0.52mmol), 15mL anhydrous THF Add it into a 50mL two-necked bottle, pass nitrogen to deoxygenate, transfer to -78°C and cool for 15min, slowly inject n-BuLi (0.23mL, 0.57mmol, 2.5M / L THF solution), continue to react at -78°C for 2h, inject Trimethyltin chloride (0.57mL, 0.57mmol, 1M / L THF solution), continued to react at -78°C for 0.5h, then transferred to room temperature for 12h. The reaction was stopped, quenched by adding 10 mL of water, the reaction solution was poured into 100 mL of distilled water, and extracted with dichloromethane (3x 30 mL). The combined organic phases were dried with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent and dried without further treatment to obtain 3.7 g of light yellow viscous liq...

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Abstract

The invention relates to a benzo[1,2-c,4,5-c']dithiophene-4,8-dione (BDD)-based electron acceptor, synthesis of an oligomer photovoltaic donor material with a (D-A)n+1D (n is equal to 1,2. . .) framework as well as application of the oligomer photovoltaic donor material to an organic solar battery. The oligomer comprises thiophene, benzene, benzodithiophene and a derivative electron donating (D) unit as well as BDD and a derivative electron acceptor (A) unit, and can serve as a donor material widely applied to a solution processing type organic solar battery. When a light active layer donor material is 5 BDTBDD, an acceptor material is 3,9-bis(2-methylene-3-(1,1-dicyanomethyl)indolone)-5,5,11,11-tetra(4-hexylphenyl)- dithiolato[2,3d,2',3'd]-s-indole[1,2-b,5,6']dithiophene (ITIC), and the highest energy conversion efficiency of bulk heterojunction oligomer solar energy is 7.89 percent when the mass ratio of the donor to the acceptor is 1,0.8. The organic solar battery is constructed bytaking the oligomer as the electron donor material and non-fullerene as the electron acceptor material, and efficient energy conversion of the device is realized.

Description

technical field [0001] The present invention relates to a class of electron acceptor units based on benzodithiophenedione (BDD), having (D-A) n+1 Synthesis of D(n=1,2...) framework oligomer photovoltaic donor materials and their application in oligomer solar cell devices. Such oligomers can be widely used as electron donor materials in solution-processed solar cells. When the electron acceptor material of the device is 3,9-bis(2-methylene-3-(1,1-dicyanomethyl)indolinone)-5,5,11,11-tetrakis(4- Hexylphenyl)-dithioene[2,3d:2',3'd]-s-indole[1,2-b:5,6']dithiophene (ITIC), donor to acceptor mass ratio When the ratio is 1:0.8, the highest energy conversion efficiency of the bulk heterojunction oligomer solar device reaches 7.89%. The present invention for the first time with (D-A) n+1 D-type oligomers are used as donor materials, and ITIC is used as non-fullerene acceptor materials to make organic solar cells, which realizes high-efficiency energy conversion of devices. Backgro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/655H10K85/6576Y02E10/549
Inventor 朱卫国夏浩王亚飞朱梦冰
Owner CHANGZHOU UNIV
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