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Benzothiadiazole-based acceptor material, and preparation method and application thereof

A technology based on benzothiadiazole and benzothiadiazole thickening, applied in the field of designing organic photoelectric materials, can solve problems such as limited absorption range, unsatisfactory short-circuit current, and enhanced molecular spectral absorption

Pending Publication Date: 2021-09-10
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aiming at the limited absorption range of the acceptor material in the active layer of the current polymer solar cell and the unsatisfactory short-circuit current, the present invention proposes a method of introducing one or three vinyl π bridges at the end of the seven-membered benzothiadiazole fused ring nucleus. Molecular design strategies to increase the conjugation length, broaden the range of electron delocalization, and significantly enhance the spectral absorption of molecules in the near-infrared region

Method used

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  • Benzothiadiazole-based acceptor material, and preparation method and application thereof
  • Benzothiadiazole-based acceptor material, and preparation method and application thereof
  • Benzothiadiazole-based acceptor material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of ultra-narrow bandgap acceptor material 1V-2F

[0028]

[0029] Synthesis of Preparation Intermediate 1: Dissolve the hydroformylated seven-membered benzothiadiazole fused-ring nucleus (560 mg, 0.5 mmol) (purchased from Suzhou Nakai Company) in 30 mL of anhydrous tetrahydrofuran, and add 1 equivalent of the hydroformylated seven-membered benzene Tributyl(1,3-dioxan-2-ylmethyl)phosphonium bromide (180mg, 0.5mmol) and sodium hydride (24mg, 0.5mmol) with thiadiazole fused ring nucleus, stirring at room temperature under nitrogen protection After 8 hours, 10 mL of dilute hydrochloric acid was added, extracted with dichloromethane, washed with deionized water, dried over anhydrous sodium sulfate and spin-dried, and purified by column chromatography to obtain intermediate 1. 1 H NMR (400MHz, CDCl 3 )δ10.14(s,1H),9.71(d,J=7.6Hz,1H),7.78(d,J=15.3Hz,1H),6.77-6.28(m,1H),4.61(t,J=7.7 Hz, 4H), 3.20(t, J=7.5Hz, 2H), 2.99(t, J=7.5Hz, 2H), 2.04(s, 2H), 1.99-1.83(m, 4H...

Embodiment 2

[0037] Synthesis of ultra-narrow bandgap acceptor material 3V-2F

[0038]

[0039]Synthesis of acceptor material 3V-2F: Intermediate 2 (69mg, 0.06mmol) and 2(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-1-ethylene ) malononitrile (52 mg, 0.22 mmol) was dissolved in 20 mL of chloroform solution, 1 ml of anhydrous pyridine was added, and reacted at 65° C. for 10 h under nitrogen protection. After the reaction, the solution was poured into methanol, and the precipitated solid was dissolved, extracted, dried, and purified by column chromatography to obtain the final product 3V-2F. 1 H NMR (400MHz, Chloroform-d) δ8.72-8.58(m,1H),8.58-8.46(m,3H),8.53-8.39(m,1H),8.33-8.20(m,1H),7.68(m ,3H),7.53-7.39(m,1H),7.42-7.30(m,1H),7.15-6.95(m,1H),4.64(s,4H),3.10-2.85(m,6H),2.10(s ,1H),1.96-1.78(m,4H),1.52-1.24(m,32H),1.19-0.82(m,30H),0.69(dd,J=16.5,6.9Hz,18H).MS(MALDI-TOF )m / z calcd.for(C 96 h 108 f 4 N 8 o 2 S 5 ):1641.7168. Found: 1641.7151.

Embodiment 3

[0041] Measuring the Optical Band Gap of Acceptor Material 1V-2F Using Absorption Spectroscopy

[0042] The acceptor material 1V-2F prepared in Example 1 is measured under chloroform and thin film UV-visible absorption spectrum as Figure 4 shown. The optical bandgap of the acceptor material can be determined by the empirical formula (E g opt =1240 / λ 吸收边缘 ) is calculated to be 1.26eV.

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Abstract

The invention discloses a benzothiadiazole-based acceptor material, and a preparation method and application thereof. An electron acceptor material of a polymer solar cell with an ultra-narrow optical band gap is obtained by taking a hydroformylation seven-membered benzothiadiazole fused ring as a core, introducing different numbers of vinyl pi bridges and then introducing a strong electron withdrawing group at the tail end. The polymer solar cell acceptor material provided by the invention has a proper energy level orbit and excellent carrier transport performance, is a potential substitute of a fullerene electron acceptor, and can be widely applied to preparation of high-performance polymer solar cell devices.

Description

technical field [0001] The invention relates to the technical field of designing organic photoelectric materials, and specifically relates to a benzothiadiazole-based acceptor material and its preparation method and application. Background technique [0002] Polymer solar cells (PSCs) have become one of the research hotspots in academia and industry because of their advantages of light weight, low cost, easy realization of large area and flexible devices. In recent years, with the rapid development of A-DA'D-A type small molecule acceptor materials, the energy conversion efficiency of polymer solar cells has exceeded 18%. However, most of the acceptor materials mainly absorb light at 500-900nm, and the absorption and utilization of light in the near-infrared region of the solar spectrum are very low. The bottleneck in the battery field is very important, and it has important guiding significance for realizing the performance of polymer solar cells to commercialization. Co...

Claims

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Application Information

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IPC IPC(8): C07D513/22H01L51/42H01L51/46
CPCC07D513/22H10K85/626H10K85/615H10K85/657H10K30/00Y02E10/549
Inventor 海杰峰李玲赵文华
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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