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Quinoxaline based copolymer, preparation method and applications thereof

A quinoxaline-based and copolymer 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, achieving novel structures and improving dissolution performance, the effect of strong fluorescent performance

Inactive Publication Date: 2015-04-15
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • 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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  • Quinoxaline based copolymer, preparation method and applications thereof
  • Quinoxaline based copolymer, preparation method and applications thereof
  • Quinoxaline based copolymer, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: The quinoxaline-based copolymer of this example, namely poly{2,6-diyl-4,8-bis(5-n-octylthiophene)benzodithiophene-co-5,8- Diyl-2,3-dimethyl-6,7-di(n-octyloxy)quinoxaline} (P1), (where R1 is n-octyl, R2 is n-octyl, n=58 ), its structural formula is as follows:

[0027]

[0028] The preparation steps of above-mentioned polymer are as follows:

[0029] The reaction formula is as follows:

[0030]

[0031] Under the protection of argon, 2,6-ditrimethyltin-4,8-bis(5-n-octylthiophene)benzodithiophene (181mg, 0.2mmol), 5,8-dibromo-2 , 3-dimethyl-6,7-bis(n-octyloxy)quinoxaline (114mg, 0.2mmol) was added into a flask filled with 10ml of toluene solvent, vacuumed to remove oxygen and filled with argon, and then added bis Triphenylphosphinepalladium dichloride (5.6mg, 0.008mmol); 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 methanol was added dropwise ...

Embodiment 2

[0034] Example 2: The quinoxaline-based copolymer of this example, namely poly{2,6-diyl-4,8-bis(5-methylthiophene)benzodithiophene-co-5,8-diyl -2,3-Dimethyl-6,7-bis(n-eicosyloxy)quinoxaline} (P2), (where R1 is methyl, R2 is n-eicosyl, n=34) , its structural formula is as follows:

[0035]

[0036] The preparation steps of above-mentioned polymer are as follows:

[0037] The reaction formula is as follows:

[0038]

[0039] Under the protection of mixed gas of nitrogen and argon, 2,6-ditrimethyltin-4,8-bis(5-methylthiophene)benzodithiophene (212mg, 0.3mmol), 5,8-dibromo- Add 2,3-dimethyl-6,7-bis(n-eicosyloxy)quinoxaline (273mg, 0.3mmol) and 15mL tetrahydrofuran into a 50mL two-necked bottle, fully dissolve and then pass nitrogen and argon After exhausting the mixed gas for about 20 minutes, tetrakistriphenylphosphine palladium (4 mg, 0.003 mmol) was added into it, and then the mixed gas of nitrogen and argon was fully ventilated for about 10 minutes, and the two-necked...

Embodiment 3

[0041] Example 3: The quinoxaline-based copolymer of this example, that is, poly{2,6-diyl-4,8-bis(5-n-eicosylthiophene)benzodithiophene-co-5, 8-diyl-2,3-dimethyl-6,7-di(methoxy)quinoxaline} (P3), (where R1 is n-eicosyl, R2 is methyl, n=56 ), its structural formula is as follows:

[0042]

[0043] The preparation steps of above-mentioned polymer are as follows:

[0044] The reaction formula is as follows:

[0045]

[0046]Under nitrogen protection, 2,6-ditrimethyltin-4,8-bis(5-n-eicosylthiophene)benzodithiophene (372mg, 0.3mmol), 5,8-dibromo-2, 3-Dimethyl-6,7-bis(methoxy)quinoxaline (124mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and tris(o-methylphenyl)phosphine (21mg, 0.06mmol ) was added to a flask containing 12 mL of N,N-dimethylformamide, and then the flask was purged with nitrogen for about 20 minutes; the flask was heated to 130° C. for Stille coupling reaction for 6 hours. Subsequently, stop the polymerization reaction after cooling down, add 40mL meth...

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Abstract

The invention belongs to the field of organic solar cell materials, and discloses a quinoxaline based copolymer, a preparation method and applications thereof. The structural formula of the copolymer is shown in the description, in the formula, the R represents a C1-C20 alkyl group and the n represents an integer in a range of 34 to 91. In the provided quinoxaline based copolymer, quinoxaline is an excellent electron acceptor unit and is advantageously for being applied to organic solar cells. The phenyl ring is modified by an alkyloxy chain so as to improve the solubility and film-forming ability of the copolymer. Phenanthrene is a compound with a large planar rigid structure, and thus has high thermal stability and a strong fluorescence performance. The light conversion rate of an organic solar cell device can be improved by applying the provided quinoxaline based copolymer to the solar cells of the organic solar cell device.

Description

technical field [0001] The invention relates to the field of organic solar cell materials, in particular to a quinoxaline-based 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...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 周明杰张振华王平陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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