Polymer containing diketopyrrolopyrrole group as well as preparation method and application thereof

A rolopyrrole diketone-based polymer technology, which is applied in the field of organic solar cell materials, can solve the problems of low conversion efficiency of inorganic solar cells, low carrier electrode collection efficiency, and mismatched spectral response to achieve excellent photovoltaic performance , novel structure, and the effect of solving low efficiency problems

Inactive Publication Date: 2014-09-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
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  • 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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  • Polymer containing diketopyrrolopyrrole group as well as preparation method and application thereof
  • Polymer containing diketopyrrolopyrrole group as well as preparation method and application thereof
  • Polymer containing diketopyrrolopyrrole group as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The polymer containing diketopyrrolopyrrole in this example, namely poly{2,6-diyl-4,8-bis(5-n-octylthiophene)benzodithiophene-co-3,6- Bis(5-yl-2-thienyl)-2,5-dihydro-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione} (P1), ( Among them, R1 is n-octyl, R2 is n-octyl, n=60), and its structural formula is as follows:

[0028]

[0029] The preparation steps of above-mentioned polymer are as follows:

[0030] The reaction formula is as follows:

[0031]

[0032] Under the protection of argon, 2,6-bistrimethyltin-4,8-bis(5-n-octylthiophene)benzodithiophene (181mg, 0.2mmol), 3,6-bis(5- Bromo-2-thienyl)-2,5-dihydro-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione (136.4mg, 0.2mmol) was added into a In a flask containing 10ml of toluene solvent, deoxygenate in vacuum and fill with argon, then add bistriphenylphosphinepalladium dichloride (5.6mg, 0.008mmol); heat the flask to 100°C for Stille coupling reaction for 36h. Subsequently, the polymerization reaction was stopped afte...

Embodiment 2

[0036] The polymer containing the diketopyrrolopyrrole group in this example, that is, poly{2,6-diyl-4,8-bis(5-methylthiophene)benzodithiophene-co-3,6-bis( 5-yl-2-thienyl)-2,5-dihydro-2,5-dieicosylpyrrolo[3,4-c]pyrrole-1,4-dione} (P2), ( Among them, R1 is methyl, R2 is n-eicosyl, n=10), and its structural formula is as follows:

[0037]

[0038] The preparation steps of above-mentioned polymer are as follows:

[0039] The reaction formula is as follows:

[0040]

[0041] Under the protection of mixed gas of nitrogen and argon, 2,6-ditrimethyltin-4,8-bis(5-methylthiophene)benzodithiophene (212mg, 0.3mmol), 3,6-bis(5 -Bromo-2-thienyl)-2,5-dihydro-2,5-di-eicosylpyrrolo[3,4-c]pyrrole-1,4-dione (306mg, 0.3mmol) and Add 15mL of tetrahydrofuran into a 50mL two-necked bottle, fully dissolve it, pass in 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 through nit...

Embodiment 3

[0044] The polymer containing diketopyrrolopyrrole groups in this example, that is, poly{2,6-diyl-4,8-bis(5-n-eicosylthiophene)benzodithiophene-co-3,6 -bis(5-yl-2-thienyl)-2,5-dihydro-2,5-dimethylpyrrolo[3,4-c]pyrrole-1,4-dione} (P3), ( Among them, R1 is n-eicosyl, R2 is methyl, n=84), and its structural formula is as follows:

[0045]

[0046] The preparation steps of above-mentioned polymer are as follows:

[0047] The reaction formula is as follows:

[0048]

[0049] Under nitrogen protection, 2,6-ditrimethyltin-4,8-bis(5-n-eicosylthiophene)benzodithiophene (372mg, 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 (3.5 mg, 0.015mmol) and tri(o-methoxyphenyl)phosphine (21mg, 0.06mmol) were added into a flask containing 12mL of N,N-dimethylformamide, and then the flask was purged with nitrogen for about After 20 min; the flask was heated to 130° C. for Stille coupling reaction for 6 h...

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Abstract

The invention belongs to the field of organic solar battery materials and discloses a polymer containing a diketopyrrolopyrrole group as well as a preparation method and application thereof. The polymer has the following structural formula shown in the specification, wherein R is C1-C20 alkyl, and n is an integer of 10-100. According to the polymer containing the diketopyrrolopyrrole group disclosed by the invention, diketopyrrolopyrrole (DPP) can be modified by an alkyl chain on an N atom, and when the diketopyrrolopyrrole is increased to length of thiophene connected to positions 3 and 6 of DPP, absorption range is widened and a band gap is reduced at the same time; benzodithiophene has photophysical property of being easy to modify, and a copolymer of benzodithiophene shows excellent photovoltaic property; the copolymer containing the diketopyrrolopyrrole group is applied to a solar battery, so that a problem that a solar battery is low in efficiency can be solved.

Description

technical field [0001] The invention relates to an organic solar cell material, in particular to a polymer containing a diketopyrrolopyrrole group and its 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, 1474) t...

Claims

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Application Information

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