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Isoindigo based co-polymer, and preparation method and application thereof

A technology of copolymer and isoindigo, which is applied in the field of solar cell materials, can solve the problems of low conversion efficiency of inorganic solar cells, low carrier electrode collection efficiency, and mismatched spectral response, so as to increase the adjustment of photoelectric performance and increase the solubility , the effect of solving the problem of low 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.
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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  • Isoindigo based co-polymer, and preparation method and application thereof
  • Isoindigo based co-polymer, and preparation method and application thereof
  • Isoindigo based co-polymer, and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0026] The preparation method of above-mentioned isoindigo copolymer, such as figure 1 shown, including the following steps:

[0027] S1, respectively provide compound A and compound B represented by the following structural formula,

[0028] A: 5,5'-Ditrimethyltin-4,4'-dialkyl-2,2'-bithiazole

[0029] B: 6,6'-dibromo-N,N'-dialkylisoindigo (193mg, 0.3mmol);

[0030] 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;

[0031] 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 After fully dissolving in an organic solvent, carry out the Stille coupling reaction at 70-130° C. for 6-60 hours, then cool down to stop the reaction to obtain a mixed solution, which contains the product, that is, the isoindigo having the following structur...

Embodiment 1

[0045] The isoindigo copolymer of this embodiment, that is, poly{4,4'-di-n-octyl-2,2'-bithiazole-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:

[0046]

[0047] The preparation steps of above-mentioned polymer are as follows:

[0048] The reaction formula is as follows:

[0049]

[0050] 5,5'-ditrimethyltin-4,4'-dioctyl-2,2'-bithiazole (215mg, 0.3mmol), 6,6'-dibromo-N,N'-dioctyl Diisoindigo (193mg, 0.3mmol), tridibenzylideneacetone dipalladium (13.75mg, 0.015mmol) and tri-tert-butylphosphine (24.2mg, 0.12mmol) were added into a flask containing 12mL of toluene and dissolved into a solution , fully blown nitrogen into the flask to exhaust the air for about 30 minutes, stirred at 95° C., performed Stille coupling reaction for 40 hours, and stopped the polymerization reaction after cooling down to obtain a mixed solution.

[0051] Add 40mL of methanol to the flask, carry out precipitation treatmen...

Embodiment 2

[0055] The isoindigo copolymer of the present embodiment, that is, poly{4,4'-dimethyl-2,2'-bithiazole-co-N,N'-di(n-eicosyl)isoindigo}, wherein , R 1 is methyl, R 2 It is n-eicosyl, n is 40, and its structural formula is as follows:

[0056]

[0057] The preparation steps of above-mentioned polymer are as follows:

[0058] The reaction formula is as follows:

[0059]

[0060] 5,5'-ditrimethyltin-4',4'-dimethyl-2,2'-bithiazole (104mg, 0.2mmol) and 6,6'-dibromo-N,N'-di (n-Eicosyl)isoindigo (196mg, 0.2mmol) was added into a 15ml flask of N,N-dimethylformamide, dissolved into a solution, and the flask was vacuumed to remove oxygen and filled with argon, and then added bis Triphenylphosphinepalladium dichloride (5.6mg, 0.008mmol) was stirred at 120°C for Stille coupling reaction for 12h, and the polymerization reaction was stopped after cooling down to obtain a mixed solution.

[0061] Add 50mL of methanol into the flask, carry out precipitation treatment on the mixed sol...

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Abstract

The invention belongs to the field of solar cells, and discloses an isoindigo based co-polymer, 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 provided by the invention, alkyl bithiazole is an excellent electron acceptor and is beneficial to electron delocalization, so that solubility property of the polymer can be increased and photoelectric properties of the polymer can be adjusted by connecting the alkyls; and isoindigo contains centrosymmetric pyrrolidone cores, so that an alkylation reaction of N atoms becomes very easily, and the solubility property and the photoelectric properties of the polymer can be adjusted by adjusting groups on the N atoms.

Description

technical field [0001] The invention relates to the field of solar cell materials, in particular to an isoindigo 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, 1992,258,1474) that conj...

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 周明杰王平张振华梁禄生
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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