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Organic semiconductor material containing benzothiadiazole unit and preparation method thereof, and solar cell device

An organic semiconductor, benzothiadiazole technology, applied in semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems of low maximum energy conversion efficiency, achieve low cost of raw materials, reduce process flow, dissolve good performance

Inactive Publication Date: 2014-12-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the highest energy conversion efficiency of solution-processable organic small molecule solar cells is still lower than that of corresponding polymers, its well-defined molecular structure, defined molecular weight, and high purity make small molecule-based organic solar cells a new research topic. hotspot
[0003] At present, but compared with organic polymer solar cells, organic small molecule solar cells still have many shortcomings

Method used

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  • Organic semiconductor material containing benzothiadiazole unit and preparation method thereof, and solar cell device
  • Organic semiconductor material containing benzothiadiazole unit and preparation method thereof, and solar cell device
  • Organic semiconductor material containing benzothiadiazole unit and preparation method thereof, and solar cell device

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preparation example Construction

[0034] The preparation method of the organic semiconductor material containing benzothiadiazole unit of one embodiment, comprises the following steps:

[0035] Step S1, providing compound A and compound B.

[0036] The structural formula of compound A is: Among them, R is C 1 ~C 20 of alkyl.

[0037] The structural formula of compound B is:

[0038] Step S2, preparing an organic semiconductor material containing benzothiadiazole units.

[0039] In an oxygen-free environment, add compound A and compound B at a molar ratio of 1:2 to 1:2.4 into an organic solvent containing a catalyst and an alkali solution, and perform a Suzuki coupling reaction at 70°C to 130°C for 12 hours to 48 hours , the catalyst is an organic palladium or a mixture of organic palladium and organic phosphorus ligand, to obtain the organic semiconductor material containing benzothiadiazole unit represented by the following structural formula:

[0040]

[0041] In this embodiment, the Suzuki coupl...

Embodiment 1

[0057] This embodiment discloses a benzothiadiazole donor organic semiconductor material (BTH1) with the following structural formula: 4,4'-(5,5'-(benzo[c][1,2,5]thiadiazole Oxadiazole-4,7-diyl)bis(4-n-octylthiophene-5,2-diyl))bis(N,N-phenylaniline), its structural formula is as follows:

[0058]

[0059] The preparation process of the above-mentioned organic semiconductor material containing benzothiadiazole unit is as follows:

[0060] Under argon protection, 4,7-bis(5-bromo-3-n-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (121mg, 0.2mmol) , N, N-diphenyl-4-pinacol borate aniline (148mg, 0.4mmol) was added into a flask containing 10ml of toluene solvent, and after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added to In the flask, the oxygen was vacuumed and filled with argon, and then bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol) was added; the flask was heated to 100°C for Suzuki coupling reaction for 24h. Subsequently, stop the re...

Embodiment 2

[0068] This embodiment discloses a benzothiadiazole donor organic semiconductor material (BTH2) with the following structural formula, namely: 4,4'-(5,5'-(benzo[c][1,2,5] Thiadiazole-4,7-diyl)bis(4-methylthiophene-5,2-diyl))bis(N,N-phenylaniline), its structural formula is as follows:

[0069]

[0070] The preparation process of the above-mentioned organic semiconductor material containing benzothiadiazole unit is as follows:

[0071] Under the protection of mixed gas of nitrogen and argon, 4,7-bis(5-bromo-3-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (146mg, 0.3mmol ), N,N-diphenyl-4-pinacol borate aniline (234mg, 0.63mmol) and 15mL tetrahydrofuran were added to a 50mL two-necked bottle, and after fully dissolved, a mixture of nitrogen and argon was introduced to exhaust the air After about 20 minutes, tetrakistriphenylphosphine palladium (4mg, 0.003mmol) was added into it, and after fully dissolving, sodium bicarbonate (3mL, 2mol / L) solution was added, and the mixed g...

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Abstract

An organic semiconductor material containing a benzothiadiazole unit has the following structural formula described in the specification, wherein R represents a C1 to C20 alkyl group. The organic semiconductor material containing the benzothiadiazole unit is a donor-acceptor type conjugated monomer, and has relatively high hole mobility, high open circuit voltage, relatively good solubility, and relatively good film-forming performance, so that the problem of low efficiency of a solar cell device is solved. The invention also provides a preparation method of the organic semiconductor material containing the benzothiadiazole unit and the solar cell device using the organic semiconductor material containing the benzothiadiazole unit.

Description

【Technical field】 [0001] The invention relates to the field of optoelectronics, in particular to an organic semiconductor material containing a benzothiadiazole unit, a preparation method thereof, and a solar battery device using the organic semiconductor material containing a benzothiadiazole unit. 【Background technique】 [0002] Bulk heterojunction solar cells have attracted widespread attention because of their low cost, light weight, simple fabrication process, and large-area flexible devices. The highest energy conversion efficiency of polymer solar cells based on conjugated polymer donors and fullerene derivative acceptors reached 9.2%. Although the highest energy conversion efficiency of solution-processable organic small molecule solar cells is still lower than that of corresponding polymers, its well-defined molecular structure, defined molecular weight, and high purity make small molecule-based organic solar cells a new research topic. hotspot. [0003] At presen...

Claims

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Application Information

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IPC IPC(8): C07D417/14H01L51/46
CPCC07D417/14H10K85/655H10K85/631H10K85/657Y02E10/549
Inventor 周明杰张振华王平陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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