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A class of a with thiazolothiazole as the core 2 -π-a 1 -π-a 2 Preparation and Application of Small Molecule Acceptor Materials

A small molecule acceptor, thiazolo technology, applied in the application of electron acceptor in the field of organic photovoltaic cells, in the field of preparation of A2-π-A1-π-A2 type small molecule acceptor materials, which can solve the problem of film formation stability Difficulty in performance adjustment and high synthesis cost

Active Publication Date: 2020-07-07
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis cost of acceptor materials based on the large fused ring center structure is high, and the stability of film formation is difficult to adjust

Method used

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  • A class of a with thiazolothiazole as the core <sub>2</sub> -π-a <sub>1</sub> -π-a <sub>2</sub> Preparation and Application of Small Molecule Acceptor Materials
  • A class of a with thiazolothiazole as the core <sub>2</sub> -π-a <sub>1</sub> -π-a <sub>2</sub> Preparation and Application of Small Molecule Acceptor Materials
  • A class of a with thiazolothiazole as the core <sub>2</sub> -π-a <sub>1</sub> -π-a <sub>2</sub> Preparation and Application of Small Molecule Acceptor Materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] A with thiazolothiazole as the nucleus 2 -π-A 1 -π-A 2 Synthesis of small molecule receptor material TTz1.

[0050] The synthetic route of TTz1 is as follows:

[0051]

[0052] 1. Synthesis of 12-bromo-3-(2-butyloctyl)thiophene (2)

[0053] In a 250 mL three-necked flask, sequentially add compound 1 (10 g, 39.6 mmol), N-bromosuccinimide (8.46 g, 47.6 mmol), and 150 mL of glacial acetic acid. Under the protection of light, react at room temperature for 12 hours, stop the reaction, transfer the reaction solution to a separatory funnel, add 50mL distilled water, extract with dichloromethane, dry over anhydrous magnesium sulfate, distill the organic solvent under reduced pressure, and the residue is distilled with petroleum ether Column chromatography was used as the eluent to obtain compound 2 as a colorless oil (12.2 g, yield 93%). 1 H NMR (400MHz, CDCl 3 )δ7.18(d, J=5.6Hz, 1H), 6.76(d, J=5.6Hz, 1H), 2.49(d, J=7.2Hz, 2H), 1.65(dd, J=11.1, 5.9Hz, 1H), 1.29-1.24 (...

Embodiment 2

[0066] A with thiazolothiazole as the nucleus 2 -π-A 1 -π-A 2 Synthesis of small molecule receptor material TTz2.

[0067] The synthetic route of TTz2 is as follows:

[0068]

[0069] In a 100mL two-neck flask, sequentially add compound 7 (200mg, 0.21mmol), compound 8 (382mg, 2.07mmol), triethylamine (0.5mL) and chloroform (60mL), under the protection of nitrogen, reflux reaction at 65°C 24h. Cool to room temperature, pour into 200 mL of anhydrous methanol for precipitation, filter with suction, and use chloroform as the eluent to separate the crude product by column chromatography, recrystallize from chloroform and acetone to obtain a maroon solid with metallic luster Compound TTz2 (230 mg, 83% yield). 1 H NMR (400MHz, CDCl 3 )δ8.32(s,1H),7.95(s,1H),7.76(d,J=7.7Hz,1H),7.56(d,J=7.7Hz,1H),4.35-4.29 (m,2H), 2.94-2.82 (m, 2H), 1.89 (t, J=16.9Hz, 1H), 1.51-1.26 (m, 19H), 0.97-0.87 (m, 6H).

Embodiment 3

[0071] Performance characterization of small molecule acceptor materials TTz1 and TTz2 and preparation and testing of photovoltaic devices:

[0072] of the synthesized compound 1 The H NMR spectrum was measured by Bruker Dex-300 NMR or 400NMR instrument, the UV-visible absorption spectrum was measured by Shimadzu UV-800 UV-visible spectrophotometer, and the cyclic voltammetry curve was tested by CHI630E electrochemical analyzer.

[0073] An organic solar cell device based on this type of small molecule acceptor material includes an indium tin oxide (ITO) conductive glass anode, a cathode modification layer, a photoactive layer, an anode modification layer, and a cathode. The active layer material is the small molecule acceptor material described in the present invention and a commercially purchased polymer donor material, and the blending weight ratio is 1:2.

[0074] 3.1 Determination of photophysical properties of small organic molecule receptors TTz1 and TTz2

[0075] fi...

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Abstract

The invention relates to a class of A with thiazolothiazole weak electron acceptor group as the core 2 -π-A 1 -π-A 2 The preparation of small molecule acceptor materials, and the application of such materials as electron acceptor materials in the photoactive layer in the field of organic photovoltaic cells. This type of small-molecule acceptor material only contains single / double aromatic rings, and has the characteristics of simple structure, few synthesis steps and excellent performance. Using this kind of small molecule acceptor material and polymer donor material, a bulk heterojunction organic solar cell was fabricated through a solution processing method, and the maximum energy conversion efficiency of the cell device was as high as 8.77%. The present invention realizes A 2 -π-A 1 -π-A 2 The high-efficiency energy conversion of small-molecule acceptor materials in organic polymer solar cells has strong application prospects.

Description

technical field [0001] The invention relates to the field of organic photovoltaics, in particular to a class of A with a simple structure and a weak electron acceptor unit of thiazolothiazole as the core. 2 -π-A 1 -π-A 2 The preparation of small molecule acceptor materials, and the application of such materials as electron acceptors in the photoactive layer in the field of organic photovoltaic cells. Background technique [0002] With the rapid development of today's world economy, energy and environmental crises are becoming more and more serious, and people's demand for clean energy is becoming more and more urgent. As an inexhaustible and inexhaustible green energy, how to efficiently utilize solar energy has become a research hotspot for scientists. Organic solar cells (OSCs) can efficiently convert solar energy into electrical energy, and have the characteristics of low cost, light weight, translucency, flexibility and bendability, which make it show great applicatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04H01L51/46H01L51/42
CPCC07D513/04H10K85/649H10K85/655H10K85/656H10K85/6565H10K85/657H10K85/6576H10K30/00Y02E10/549
Inventor 朱卫国彭文红张斌朱梦冰顾子倩马超
Owner CHANGZHOU UNIV
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