Thiophene pyrroledione based co-polymer organic semiconductor material, and preparation method and application thereof

A pyrrole diketo-based copolymer and organic semiconductor technology, applied in the field of solar cell materials, can solve problems such as low conversion efficiency of inorganic solar cells, and achieve the effects of increasing carrier mobility, reducing bandwidth, and prolonging conjugation performance.

Inactive Publication Date: 2013-06-19
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since 1992, N.S.Sariciftci et al reported on SCIENCE (N.S Sariciftci, L.Smilowitz, A.J.Heeger, et al.Science, 1992,258,1474) that conjugated polymers and C 60 After the phenomenon of light-induced electron transfer between polymer solar cells, people have invested a lot of research in polymer solar cells and achieved rapid development, but the conversion efficiency is still much lower than that of inorganic solar cells.

Method used

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  • Thiophene pyrroledione based co-polymer organic semiconductor material, and preparation method and application thereof
  • Thiophene pyrroledione based co-polymer organic semiconductor material, and preparation method and application thereof
  • Thiophene pyrroledione based co-polymer organic semiconductor material, and preparation method and application thereof

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Experimental program
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Effect test

preparation example Construction

[0029] The preparation method of the above-mentioned thienopyrrole diketopyl copolymer organic semiconductor material, such as figure 1 shown, including the following steps:

[0030] S1, respectively provide compound A and compound B represented by the following structural formula,

[0031] A: 2,6-Ditrimethyltin-4,4-dialkylcyclopentane[2,1-b:3,4-b']dithiophene

[0032] B: N-Alkyl-2,5-dibromo-thieno[3,4-c]pyrrole-4,6-dione

[0033] Among them, in compound A, R 1 for C 1 ~C 20 The alkyl; compound B, R 2 for C 1 ~C 20 the alkyl group;

[0034] S2. In an oxygen-free environment (such as an oxygen-free environment composed of nitrogen, argon, or a mixture of nitrogen and argon), the compound A and compound B are added in a molar ratio of 1:1 into the catalyst containing After fully dissolving in an organic solvent, carry out the Stille coupling reaction at 70-130° C. for 6-60 hours, then cool down to stop the reaction to obtain a mixed solution, which contains the prod...

Embodiment 1

[0047]The thienopyrrole diketopyl copolymer organic semiconductor material in this example, that is, poly{4,4-di-n-octylcyclopentane[2,1-b:3,4-b']dithiophene-co- N-n-octyl-thiophene[3,4-c]pyrrole-4,6-dione}, wherein, R 1 is n-octyl, R 2 Be n-octyl, n is 60, and its structural formula is as follows:

[0048]

[0049] The preparation steps of above-mentioned polymer are as follows:

[0050] The reaction formula is as follows:

[0051]

[0052] 2,6-Ditrimethyltin-4,4-di-n-octylcyclopentane[2,1-b:3,4-b']dithiophene (218mg, 0.3mmol), N-n-octyl Dibromo-2,5-dibromo-thieno[3,4-c]pyrrole-4,6-dione (126mg, 0.3mmol), tridibenzylideneacetone dipalladium (13.75mg, 0.015mmol) and tri Add tert-butylphosphine (24.2mg, 0.12mmol) into a flask containing 12mL of toluene, dissolve it into a solution, fully blow nitrogen into the flask and exhaust the air for about 30min, then stir at 95°C for Stille coupling reaction for 40h, stop after cooling down Polymerization reaction to obtain a ...

Embodiment 2

[0057] The thienopyrrole diketopyl copolymer organic semiconductor material in this example, that is, poly{4,4-dimethylcyclopentane[2,1-b:3,4-b']dithiophene-co-N -eicosylthiophene[3,4-c]pyrrole-4,6-dione}, wherein, R 1 is methyl, R 2 It is n-eicosyl, n is 40, and its structural formula is as follows:

[0058]

[0059] The preparation steps of above-mentioned polymer are as follows:

[0060] The reaction formula is as follows:

[0061]

[0062] 2,6-Ditrimethyltin-4,4-dimethylcyclopentane[2,1-b:3,4-b']dithiophene (106mg, 0.2mmol) and N-eicosane Base-2,5-dibromo-thieno[3,4-c]pyrrole-4,6-dione (118mg, 0.2mmol) was added into a 15ml N,N-dimethylformamide flask, dissolved into a solution, vacuumize the flask to deoxygenate and fill it with argon, then add bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol), stir at 110°C, Stille coupling reaction for 12h, stop the polymerization reaction after cooling down, Obtain a mixture.

[0063] Add 50mL of methanol into t...

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Abstract

The invention belongs to the field of solar cells, and discloses a thiophene pyrroledione based co-polymer organic semiconductor material, and a preparation method and an application thereof. The co-polymer has the following structural formula (I). In the formula, both R1 and R2 represent a C1-C20 alkyl group and n is an integer ranging from 10 to 100. In the thiophene pyrroledione based co-polymer organic semiconductor material provided by the invention, cyclopentadithiophene has a completely planar crystal structure, two thiophene rings in the structural unit of the cyclopentadithiophene are in the same plane, and the structure can effectively extend conjugated performance of a polymer and reduce a band gap of the polymer. Besides, the coplanar structure makes transfer of carriers between two main chains become easier, thereby increasing the carrier mobility. The above performances can improve energy conversion efficiency of solar energy, so that the problem of low efficiency of polymer solar cells is solved.

Description

technical field [0001] The invention relates to the field of solar cell materials, in particular to a thienopyrrole diketopyl copolymer organic semiconductor material and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. At present, the silicon crystal cells used for the ground are limited in application due to the complicated production process and high cost. In order to reduce the cost of batteries and expand the application range, people have been looking for new solar cell materials for a long time. Organic semiconductor materials have attracted much attention due to the advantages of readily available raw materials, low cost, simple preparation process, good environmental stability, and good photovoltaic effect. Since 1992, N.S.Sariciftci et al reported on SCIENCE (N.S Sariciftci, L.Smilo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 周明杰王平张振华陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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