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Diketopyrrolopyrrole-base polymer, and preparation method and application thereof

A pyrrolopyrrole diketo-polymer technology, which is applied in the field of solar cell materials, can solve the problems of mismatched spectral response, low conversion efficiency of inorganic solar cells, low collection efficiency of carrier electrodes, etc., and achieves the effect of strong absorption

Inactive Publication Date: 2014-03-26
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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.
The main constraints that limit the improvement of performance are: the spectral response of organic semiconductor materials does not match the spectrum of solar radiation, the relatively low carrier mobility of organic semiconductors, and the low electrode collection efficiency of carriers, etc.

Method used

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  • Diketopyrrolopyrrole-base polymer, and preparation method and application thereof
  • Diketopyrrolopyrrole-base polymer, and preparation method and application thereof
  • Diketopyrrolopyrrole-base polymer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The diketopyrrolopyrrole polymer of this example, that is, poly{2,6-diyl-4,8-bis(n-octyloxy)benzodithiophene-co-3,6-bis(5-yl -2-thienyl)-2,5-dihydro-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione}, wherein R1 is n-octyl, R2 is n-octyl, n=53; its structural formula is as follows:

[0034]

[0035] The preparation steps of above-mentioned polymer are as follows:

[0036] The reaction formula is as follows:

[0037]

[0038] Under the protection of argon, 2,6-ditrimethyltin-4,8-bis(n-octyloxy)benzodithiophene (151 mg, 0.2 mmol), 3,6-bis(5-bromo-2 -Thienyl)-2,5-dihydro-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4-dione (136.4mg, 0.2mmol) was added to 10ml of toluene solvent In the flask, the oxygen was evacuated and filled with argon, and then bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol) was added; the flask was heated to 100°C for Stille coupling reaction for 36h. Subsequently, the polymerization reaction was stopped after cooling down, and 50 ml of metha...

Embodiment 2

[0042] The diketopyrrolopyrrole polymer of this example, that is, poly{2,6-diyl-4,8-bis(methoxy)benzodithiophene-co-3,6-bis(5-yl- 2-thienyl)-2,5-dihydro-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione}, wherein, R1 is methyl, R2 is normal Eicosyl, n=10; its structural formula is as follows:

[0043]

[0044] The preparation steps of above-mentioned polymer are as follows:

[0045] The reaction formula is as follows:

[0046]

[0047]Under the protection of mixed gas of nitrogen and argon, 2,6-ditrimethyltin-4,8-bis(methoxy)benzodithiophene (173mg, 0.3mmol), 3,6-bis(5-bromo -2-thienyl)-2,5-dihydro-2,5-dieicosylpyrrolo[3,4-c]pyrrole-1,4-dione (306mg, 0.3mmol) and 15mL tetrahydrofuran Add it into a 50mL two-necked bottle, fully dissolve it, and then pass a mixture of nitrogen and argon to exhaust the air for about 20 minutes, then add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) into it, and then fully pass nitrogen and argon After the mixed gas was exhausted for...

Embodiment 3

[0050] The diketopyrrolopyrrole polymer of this example, namely poly{2,6-diyl-4,8-bis(n-eicosyloxy)benzodithiophene-co-3,6-bis(5 -yl-2-thienyl)-2,5-dihydro-2,5-dimethylpyrrolo[3,4-c]pyrrole-1,4-dione}, wherein R1 is n-eicosane base, R2 is a methyl group, n=75; 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] Under nitrogen protection, 2,6-ditrimethyltin-4,8-bis(n-eicosyloxy)benzodithiophene (332mg, 0.3mmol), 3,6-bis(5-bromo-2 -Thienyl)-2,5-dihydro-2,5-dimethylpyrrolo[3,4-c]pyrrole-1,4-dione (160.4mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and tri(o-methoxyphenyl)phosphine (21mg, 0.06mmol) were added to a flask containing 12mL of N,N-dimethylformamide, and then the flask was purged with nitrogen for about 20min. ; The flask was heated to 130 ° C for Stille coupling reaction 6h. Subsequently, stop the polymerization reaction a...

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Abstract

The invention belongs to the field of solar cell materials, and discloses a diketopyrrolopyrrole-base polymer which has the following structural formula, wherein R1 and R2 are respectively a C1-C20 alkyl group, and n is a whole number ranging from 10 to 100. In the diketopyrrolopyrrole-base copolymer, the DPP has the advantages of high absorptivity, high photochemical stability and the like; the DPP can modify the alkyl chain through N atoms; when the lengths of thiophenes connected to the 3 site and 6 site of the DPP are increased, the absorption range becomes wider, and the band gap becomes smaller; and all of the properties can enhance the energy conversion efficiency of the organic solar cell.

Description

technical field [0001] The invention relates to the field of solar cell materials, in particular to a diketopyrrolopyrrole polymer and a preparation method thereof. The present invention also relates to the use of the diketopyrrolopyrrole polymer in organic solar cells. 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 e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/30H01L51/54
Inventor 周明杰王平张振华冯小明
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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