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

A pyrrole diketo-based and copolymer technology is applied in the field of solar cell materials, which can solve the problems of low conversion efficiency of inorganic solar cells and the like, and achieve the effects of excellent photovoltaic performance, improved open circuit voltage and improved energy conversion efficiency.

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 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.

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

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preparation example Construction

[0031] The preparation method of above-mentioned thienopyrrole diketopyl copolymer material, such as figure 1 shown, including the following steps:

[0032] S1, respectively provide compound A and compound B represented by the following structural formula,

[0033] 2,6-Ditrimethyltin-4,8-dialkoxybenzodithiophene

[0034] N-Alkyl-thieno[3,4-c]pyrrole-4,6-dione

[0035] 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;

[0036] 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 the organic solvent, after fully dissolving, carry out Stille coupling reaction at 70~130 ℃ for 6~60h, after cooling down to stop the reaction, a mixed solution is obtained, and the mixed solution contains the product, that is, the thiophene having the f...

Embodiment 1

[0050] The thienopyrrole diketopyl copolymer material of this embodiment, that is, poly{4,8-di(octyloxy)benzodithiophene-co-N-octyl-thiophene[3,4-c]pyrrole- 4,6-diketone} (wherein, R 1 is n-octyl, R 2 Be n-octyl, n is 60), its structural formula is as follows:

[0051]

[0052] The preparation steps of above-mentioned polymer are as follows:

[0053] The reaction formula is as follows:

[0054]

[0055] 2,6-Ditrimethyltin-4,8-bis(n-octyloxy)benzodithiophene (232mg, 0.3mmol), N-n-octyl-2,5-dibromo-thiophene[3, 4-c] pyrrole-4,6-dione (126mg, 0.3mmol), tridibenzylideneacetone dipalladium (13.75mg, 0.015mmol) and tri-tert-butylphosphine (24.2mg, 0.12mmol) were added to the Dissolve in a flask with 12mL of toluene to form a solution, fully ventilate nitrogen into the flask for about 30 minutes, stir at 95°C, and conduct Stille coupling reaction for 40 hours. After cooling down, stop the polymerization reaction to obtain a mixed solution.

[0056] Add 40mL of methanol to th...

Embodiment 2

[0060] The thienopyrrole diketopecopolymer material of this embodiment, that is, poly{4,8-di(methoxy)benzodithiophene-co-N-n-eicosyl-thiophene[3,4-c] And pyrrole-4,6-dione} (wherein, R 1 is methyl, R 2 Be n-eicosyl, n is 40), its structural formula is as follows:

[0061]

[0062] The preparation steps of above-mentioned polymer are as follows:

[0063] The reaction formula is as follows:

[0064]

[0065] 2,6-Ditrimethyltin-4,8-bis(methoxy)benzodithiophene (115mg, 0.2mmol) and N-n-eicosyl-2,5-dibromo-thiophene[3 ,4-c] pyrrole-4,6-dione (118mg, 0.2mmol) was added into a 15ml N,N-dimethylformamide flask, dissolved into a solution, and the flask was evacuated to remove oxygen and filled with argon Then add bistriphenylphosphinepalladium dichloride (5.6mg, 0.008mmol), stir at 120°C, conduct Stille coupling reaction for 12h, stop the polymerization reaction after cooling down, and obtain a mixed solution.

[0066] Add 50mL of methanol into the flask, carry out precipita...

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Abstract

The invention belongs to the field of solar cells, and discloses a thiophene pyrroledione based co-polymer 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 material provided by the invention, benzo-dithiophene has easily modified photophysical properties, the co-polymer of the benzo-dithiophene present excellent photovoltaic performance; thiophene pyrroledione has a simple, symmetrical and polar structure and is beneficial to electron delocalization when the thiophene pyrroledione is polymerized with other monomers; and the thiophene pyrroledione has relatively strong electron-withdrawing effect that results in reduction of an HOMO energy level and a LUMO energy level, thereby facilitating the increase of an open-circuit voltage. The performance 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 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 that conjugated polymers and C 60 After the phenomenon of light-indu...

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 周明杰王平张振华黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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