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

A technology of organic semiconductors and copolymers, applied in the field of solar cell materials, can solve the problems of low conversion efficiency of inorganic solar cells, achieve the effects of increasing carrier mobility, reducing bandwidth, and improving open circuit voltage

Inactive Publication Date: 2013-06-19
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • 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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  • Isoindigo based co-polymer organic semiconductor material, and preparation method and application thereof
  • Isoindigo based co-polymer organic semiconductor material, and preparation method and application thereof
  • Isoindigo based co-polymer organic semiconductor material, and preparation method and application thereof

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preparation example Construction

[0030] The preparation method of the above-mentioned isoindigo copolymer organic semiconductor material, such as figure 1 shown, including the following steps:

[0031] S1, respectively provide compound A and compound B represented by the following structural formula,

[0032] 2,6-Ditrimethyltin-4,4-dialkylcyclopentane[2,1-b:3,4-b']dithiophene;

[0033] 6,6'-dibromo-N,N'-dialkylisoindigo (193mg, 0.3mmol);

[0034] Among them, in compound A, R 1 for C 1 ~C 20 The alkyl group; in compound B, R 2 for C 1 ~C 20 the alkyl group;

[0035] 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 In an organic solvent, after fully dissolving, carry out the Stille coupling reaction at 70-130° C. for 12-96 hours, then cool down to stop the reaction to obtain a mixed solution, which contains the product, t...

Embodiment 1

[0049] The isoindigo copolymer organic semiconductor material of this embodiment, that is, poly{4,4-di-n-octylcyclopentane[2,1-b:3,4-b']dithiophene-co-N,N '-Di-n-octylisoindigo}, wherein, R 1 is n-octyl, R 2 Be n-octyl, n is 60, and its structural formula is as follows:

[0050]

[0051] The preparation steps of above-mentioned polymer are as follows:

[0052] The reaction formula is as follows:

[0053]

[0054] 2,6-Ditrimethyltin-4,4-dioctylcyclopentane[2,1-b:3,4-b']dithiophene (218mg, 0.3mmol), 6,6'- Dibromo-N, N'-dioctylisoindigo (193mg, 0.3mmol), tridibenzylideneacetone dipalladium (13.75mg, 0.015mmol), tri-tert-butylphosphine (24.2mg, 0.12mmol) Put in a flask with 12mL of toluene, and then pass nitrogen gas to exhaust the air for about 30min, stir at 95°C, conduct Stille coupling reaction for 40h, stop the polymerization reaction after cooling down, and obtain a mixed solution.

[0055] Add 40mL of methanol to the flask, carry out precipitation treatment on th...

Embodiment 2

[0059] The isoindigo copolymer organic semiconductor material of this embodiment, that is, poly{4,4-dimethylcyclopentane[2,1-b:3,4-b']dithiophene-co-N,N' - two (n-eicosyl) isoindigo}, wherein, R 1 is methyl, R 2 It is n-eicosyl, n is 40, and its structural formula is as follows:

[0060]

[0061] The preparation steps of above-mentioned polymer are as follows:

[0062] The reaction formula is as follows:

[0063]

[0064] 2,6-Ditrimethyltin-4,4-dimethylcyclopentane[2,1-b:3,4-b']dithiophene (106mg, 0.2mmol) and 6,6'- Dibromo-N,N'-bis(eicosyl)isoindigo (196mg, 0.2mmol)) was added into a flask containing 15ml of N,N-dimethylformamide solvent, dissolved into a solution, and the flask was evacuated Deoxygenated and filled with argon, then bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol) was added, stirred at 120°C, and subjected to Stille coupling reaction for 12h. After cooling down, the polymerization reaction was stopped to obtain a mixed solution.

[006...

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Abstract

The invention belongs to the field of solar cells, and discloses an isoindigo 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 isoindigo 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.

Description

technical field [0001] The invention relates to the field of solar cell materials, in particular to an isoindigo 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. Due to the complex production process and high cost of silicon cells currently used on the ground, their application is limited. 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.Smilowitz, A.J.Heeger, et al.Sc...

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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