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D(A-Ar)2-type conjugate compound based on dithiophene benzoisoaromatic heterocyclic fused ring and application of D(A-Ar)2-type conjugate compound

A technology of conjugated compounds and alkyl thiophene groups, applied in the field of organic small molecule photovoltaics, can solve the problems of complex device preparation, poor performance repeatability, and low service life, and achieve wide spectral band response, narrow band gap, and good film-forming performance Effect

Active Publication Date: 2019-07-12
CHANGZHOU UNIV
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Problems solved by technology

The promotion and application of inorganic solar cells are limited to some extent due to the high cost of preparation, large energy loss during processing, and environmental pollution caused by waste products.
Dye-sensitized solar cells, the liquid electrolyte increases the difficulty of device preparation, and has some disadvantages such as toxicity and serious heavy metal pollution.
Although perovskite solar cells have high photoelectric conversion efficiency, they have become a research hotspot in recent years. However, their complicated device preparation, poor performance repeatability and low service life will also restrict their wide application.

Method used

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  • D(A-Ar)2-type conjugate compound based on dithiophene benzoisoaromatic heterocyclic fused ring and application of D(A-Ar)2-type conjugate compound
  • D(A-Ar)2-type conjugate compound based on dithiophene benzoisoaromatic heterocyclic fused ring and application of D(A-Ar)2-type conjugate compound
  • D(A-Ar)2-type conjugate compound based on dithiophene benzoisoaromatic heterocyclic fused ring and application of D(A-Ar)2-type conjugate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056]5,5,10,10-Tetrakis(dodecyl)-7-(2-(thienyl)-5-hydro-dithiophene[3,2-c]isobenzopyran containing ditin substitution The synthesis of its synthetic route is shown in the figure below.

[0057]

[0058] 1.1 Synthesis of 2-(tributyltin)-3-methoxythiophene (1)

[0059] 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, then react at room temperature for 2h. Put again at -78°C and add tributyltin chloride (14.3g, 44mmol) dropwise at once, and react 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 layers were washed with saturated brine three times, 50 mL each time. The organic layer was spin-dried under reduced pressure and dried in vacuo to obtain a pale yellow liquid (15.5 g, 98.0%). 1 HNMR (4...

Embodiment 2

[0071] Synthesis of 4-bromo-5,6-difluoro-7-(5-(9-octyl-9hydro-carbazole-3-)thiophene-2-)1,2,5-benzothiadiazole

[0072]

[0073] 2.1 Synthesis of 9-octyl-3-(thiophene-2-)-9-hydrogen-carbazole

[0074] Add 20mL of toluene, 3-bromo-9-octyl-9-hydrogen-carbazole (1.5g, 4.19mmol), 2-thiophene tributyltin (1.88g, 5.03mmol), bis(triphenyl Phosphine)palladium dichloride (88mg, 0.13mmol). Stir and heat to 110° C. under a nitrogen atmosphere, stop the reaction after 12 h, and cool to room temperature. The solvent was removed by rotary evaporation, and the mixed solution of petroleum ether / dichloromethane with a volume ratio of 5:1 was used as the eluent for column chromatography to obtain 1.36 g of the product with a yield of 90.0%. 1 HNMR (400MHz, CDCl 3 )δ8.32(s,1H),8.14(d,J=8.0Hz,1H),7.73(dd,J=8.5,1.8Hz,1H),7.50–7.45(m,1H),7.44–7.37(m ,2H),7.34(dd,J=3.5,1.1Hz,1H),7.26(d,J=1.1Hz,1H),7.11(dd,J=4.0,4.0Hz,1H),4.30(t,J= 8.0Hz, 2H), 1.88(m, 2H), 1.64(m, 2H), 1.35(m, 10H), 0.93(t, J...

Embodiment 3

[0080] Synthesis of 4-bromo-5,6-difluoro-7-(5'-octyl-[2,2'-dithiophene]-5-)1,2,5-benzothiadiazole

[0081]

[0082] Add 20mL of toluene, (5'-octyl-[2,2'-dithiophene]-5-)tributyltin chloride (1.72mg, 3.04mmol), 4,7-dibromo- 5,6-Difluoro-2,1,3-benzothiadiazole (1.0 g, 3.04 mmol), bis(triphenylphosphine)palladium dichloride (64 mg, 0.09 mmol). Stir and heat to 80°C under nitrogen atmosphere, stop the reaction after 4h, and cool to room temperature. The solvent was removed by rotary evaporation, and the mixed solution of petroleum ether / dichloromethane with a volume ratio of 5:1 was used as the eluent for column chromatography to obtain 271 mg of the product with a yield of 89.1%. 1 HNMR (CDCl 3 ,400MHz)δ8.19(d,J=4.0Hz,1H),7.24(dd,J=4.0,1.3Hz,1H),7.16(d,J=4.0Hz,1H),6.74(d,J=4.0 Hz,1H),2.82(t,J=8.0Hz,2H),1.70(dt,J=15.2,7.7Hz,2H),1.27(m,10H),0.89(t,J=8.0Hz,3H).

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a D(A-Ar)2-type conjugate compound based on dithiophene benzoisoaromatic heterocyclic fusedring as well as a preparation method and application of the D(A-Ar)2-type conjugate compound. The preparation method comprises the following steps: using methyl 2, 5-dibromo-1, 3-dicarboxylate as a central ring nucleus; and preparing organic small-molecule photovoltaic donor materials with a cyclobenzene-containing dithiophene benzoisoaromatic heterocyclic fused ring D(A-Ar)2-type structure through coupling of heterocyclic phenone derivatives, ring-closing reaction and coupling reaction. D(A-Ar)2-type conjugate molecules based on dithiophene benzoisoaromatic heterocyclic fused ring involved in the invention have excellent solubility and stability, wide spectral absorption range and appropriate energy level structure, and are expected to be used as donor materials for organic solar cells.

Description

technical field [0001] The invention relates to the field of organic small molecule photovoltaics, in particular to a class of D(A-Ar) 2 The synthesis of small organic molecules with type structure and the application of such molecules as electron donor materials in the photoactive layer in the field of organic photovoltaic cells. [0002] technical background [0003] In recent years, since the 20th century, the excessive development and use of fossil energy such as coal, oil, and natural gas has caused serious damage to water and soil resources, environmental pollution, and the emergence of extreme climates, posing a huge threat to human survival and sustainable development of society. At the same time, the increasing shortage of fossil energy and the dependence of human society on energy force people to develop clean and sustainable new energy. The development and utilization of clean energy including wind energy, water energy, biomass energy and solar energy has become t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/30H01L51/46H01L51/54
CPCC07D495/22H10K85/6576Y02E10/549
Inventor 刘煜李敏朱卫国杨振刘座吉
Owner CHANGZHOU UNIV
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