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

A diketopyrrole-based copolymer and diketopyrrole-based technology, applied in the field of solar cell materials, can solve the problems of low conversion efficiency of inorganic solar cells, achieve superior chemical stability, reduce process flow, and improve 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 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 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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Experimental program
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preparation example Construction

[0029] The preparation method of above-mentioned thienopyrrole diketopyl copolymer, 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] 2,7-diboronic acid pinacol ester-9-alkylcarbazole;

[0032] N-Alkyl-thiopheno[3,4-c]pyrrole-4,6-dione;

[0033] 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;

[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 And in the organic solvent of alkali solution, carry out Suzuki coupling reaction at 70~130 ℃ after fully dissolving after 12~96h, stop polymerization reaction after cooling down, obtain mixed solution, contain product in this mixed solution, promptly have fo...

Embodiment 1

[0048]The diketopyrrole thienopyrrole copolymer of this example, that is, poly{N-n-octyl-2,7-carbazole-co-N-n-octyl-thiophene[3,4-c]pyrrole-4, 6-diketone} (wherein, R 1 is n-octyl, R 2 Be n-octyl, n is 55), its structural formula is as follows:

[0049]

[0050] The preparation steps of above-mentioned polymer are as follows:

[0051] The reaction formula is as follows:

[0052]

[0053] 2,7-diboronic acid pinacol ester-9-n-octylcarbazole (159.3mg, 0.3mmol), N-n-octyl-2,5-dibromo-thiophene[3,4-c]pyrrole -4,6-diketone (126mg, 0.3mmol), tridibenzylideneacetone dipalladium (13.75mg, 0.015mmol), tri-tert-butylphosphine (18mg, 0.09mmol) were added to a flask containing 12mL of toluene, After fully dissolving, potassium carbonate solution (3mL, 2mol / L) was added into the flask, and then nitrogen was vented for about 30min, then stirred at 95°C, Suzuki coupling reaction was performed for 48h, and the polymerization reaction was stopped after cooling down to obtain a mixed s...

Embodiment 2

[0058] The thienopyrrole diketopyl copolymer of this example, that is, poly{N-octyl-2,7-carbazole-co-N-octyl-thiophene[3,4-c]pyrrole-4,6- Diketone} (wherein, R 1 is methyl, R 2 Be n-eicosyl, n is 40), its structural formula is as follows:

[0059]

[0060] The preparation steps of above-mentioned polymer are as follows:

[0061] The reaction formula is as follows:

[0062]

[0063] 2,7-diboronic acid pinacol ester-9-methylcarbazole (86mg, 0.2mmol) and N-n-eicosyl-2,5-dibromo-thiophene[3,4-c]pyrrole -4,6-diketone (118mg, 0.2mmol) was added into a flask filled with 15ml of N,N-dimethylformamide solvent, and dissolved into a solution; then sodium carbonate solution (2mL, 2mol / L) was added Into the flask, vacuum the flask to remove oxygen and fill it with argon, then add bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol), stir at 120°C, Suzuki coupling reaction for 24h, stop the polymerization reaction after cooling down , to obtain a mixture.

[0064] Add 5...

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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, 2,7-carbazole has good hole transport properties, excellent chemical stability and easily modified photophysical properties; 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 pyrroledionehas 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 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.Science, 1992,258,14...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46C07D519/00
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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