A2-(pi-A1)2 wide band gap non-fullerene receptor material based on diphenylthiophenyl sulfone and preparation method and application thereof

A technology of diphenylthiophenylsulfone and gap non-fullerene is applied in the field of A22 type wide band gap non-fullerene acceptor material and its preparation, which can solve the problem of complex preparation process and few varieties of wide band gap small molecule acceptor materials. and other problems, to achieve narrow spectral absorption, promote π-π stacking, and promote the transmission and separation of excitons.

Inactive Publication Date: 2018-12-25
CHANGZHOU UNIV
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0026] Aiming at the current problems of few varieties of wide-bandgap small-molecule acceptor materials with excellent performance and complicated fabrication process to obtain high-efficiency conversion devices, a diphenylthiophenylsulfone-based A 2 (π-A 1 ) 2 wide bandgap non-fullerene acceptor material

Method used

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  • A2-(pi-A1)2 wide band gap non-fullerene receptor material based on diphenylthiophenyl sulfone and preparation method and application thereof
  • A2-(pi-A1)2 wide band gap non-fullerene receptor material based on diphenylthiophenyl sulfone and preparation method and application thereof
  • A2-(pi-A1)2 wide band gap non-fullerene receptor material based on diphenylthiophenyl sulfone and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] A 2 (π-A 1 ) 2 Synthesis of intermediates of wide bandgap small molecule non-fullerene acceptor materials (M1, M2, M3, M4, M5, M6 and M7), the synthesis route is shown below.

[0069]

[0070] 1.1 Synthesis of 2-(tri-n-butyltin base)-4-butyloctylthiophene (M1)

[0071]In a 100mL three-necked flask, add 2-(2-butyloctyl)thiophene (3.0g, 11.9mmol) and 40mL of freshly distilled tetrahydrofuran, stir magnetically under nitrogen protection, place the system at -78°C, and automatically Slowly add n-butyl lithium (8.5mL, 1.6M) dropwise into the constant pressure dropping funnel, after the dropwise addition, continue the reaction at low temperature for 2h, then add tributyltin chloride (4.60g, 14.3mmol) dropwise, and continue the reaction After 30min, move to room temperature for 24h. After the reaction was completed, the reaction solution was poured into 150 mL of water to quench the reaction, and the mixed solution was extracted with dichloromethane (50 mL × 3 times), t...

Embodiment 2

[0084] Example 2 Synthesis of wide bandgap non-fullerene acceptor BTO-TIC

[0085]

[0086] Add compound 7 (100mg, 0.14mmol), 3-(dicyanomethylene) indanone (130mg, 0.67mmol) and 15mL of freshly distilled tetrahydrofuran to a 50mL single-necked bottle in turn, stir magnetically, and the solid in the system dissolves completely Finally, 5 drops of pyridine were added dropwise, the system reacted rapidly, and reacted for 12 hours at room temperature. After the reaction, the reaction solution was poured into 150mL water to quench the reaction, and the mixed solution was extracted with chloroform (50mL×3 times), the organic phases were combined, anhydrous MgSO 4 Dry, filter, and spin off the solvent to obtain a purple solid crude product. The crude product is separated by column chromatography using dichloromethane / ethyl acetate=40 / 1 as the eluent to obtain a purple solid (100mg, yield=62% ). 1 H NMR (400MHz, CDCl 3 )δ8.99 (s, 2H), 8.71 (d, J = 7.1Hz, 2H), 8.20 (s, 2H), 8.02 ...

Embodiment 3

[0087] Example 3 Synthesis of wide bandgap non-fullerene acceptor BTO-TDFIC

[0088]

[0089] Refer to the synthesis and purification method of the target compound BTO-TIC. The eluent was dichloromethane / ethyl acetate=40 / 1 to obtain a purple solid (120 mg, yield=66%). 1 H NMR (400MHz, CDCl 3 )δ9.02(s,2H),8.58(dd,J=9.8,6.5Hz,2H),8.23(s,2H),8.08(d,J=8.0Hz,2H),7.90(d,J=8.1 Hz,2H),7.73(s,2H),7.48(s,2H),2.94(d,J=7.3Hz,4H),1.77(s,2H),1.30-1.25(m,32H),0.90-0.84 (m,12H).Anal.Calcd for:C 70 h 64 f 4 N 4 o 4 S 3 : C, 70.21; H, 5.39; N, 4.68; S, 8.03. Found: C, 68.54; H, 5.30; N, 4.72; S, 8.08.

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Abstract

The invention relates to a preparation method of an A2-(pi-A1)2 wide band gap non-fullerene receptor material based on diphenylthiophenyl sulfone and an application thereof in a polymer photovoltaic device. The A2-(pi-A1)2 wide band gap non-fullerene receptor material based on the diphenylthiophenyl sulfone and the preparation method and application thereof are characterized in that the diphenylthiophenyl sulfone is a weak acceptor electron (A2) unit; the pi bridge is 3-alkyl thiophene or 3-oxyalkyl thiophene; a terminal strong acceptor electron (A1) unit is cyano indanone and fluorinated andchlorinated derivatives thereof; the wide band gap non-fullerene acceptor material has an electrochemical band gap of up to 2.01 electron volts and can be used as a receptor material applied to solution-processed polymer solar cells with narrow band gap polymers; when the polymer PTB7-Th is utilized as a donor, the maximum energy conversion efficiency and open circuit voltage of bulk heterojunction polymer solar cell are 1.77% and 0.89 volts, respectively. The A2-(pi-A1)2 wide band gap non-fullerene receptor material based on the diphenylthiophenyl sulfone has the advantage of achieving efficient energy conversion of the A2(pi-A1)2 wide band gap non-fullerene receptor material in the polymer solar cells.

Description

technical field [0001] The invention relates to the field of organic solar cell materials, in particular to a diphenylthiophenyl sulfone-based A 2 (π-A 1 ) 2 Type wide bandgap non-fullerene acceptor material and its preparation method and application. technical background [0002] With the continuous consumption of coal, oil, natural gas and other fossil energy and the increasingly serious environmental pollution, the development of safe, pollution-free and easy-to-obtain new energy has become a top priority for sustainable development in all countries in the world today. Clean energy such as solar energy, wind energy, and nuclear energy has gradually attracted everyone's attention due to its advantages of wide sources, no pollution, and easy access. Because solar energy is inexhaustible, inexhaustible, safe, non-polluting, and has many advantages such as low cost, easy access, and no geographical constraints, it has become a major development strategy developed and imple...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76C07D409/14C07D421/14H01L51/46
CPCC07D333/76C07D409/14C07D421/14H10K85/649H10K85/653H10K85/655H10K85/615H10K85/6576Y02E10/549
Inventor 刘煜李啸朱卫国李敏王亚飞张斌
Owner CHANGZHOU UNIV
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