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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, and achieve novel material structures and improved Effects of solubility and strong fluorescence

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

[0027] Example 1: The quinoxaline-based copolymer of this example, that is, poly{2,2'-(9,10-bis(n-octyloxy)phenanthrene-2,7-diyl-co-5,8- Diyl-2,3-dimethyl-6,7-di(n-octyloxy)quinoxaline} (P1), (where R1 is n-octyl, R2 is n-octyl, n=52 ), 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, 2,2'-(9,10-di(n-octyloxy)phenanthrene-2,7-dipinacol borate (137mg, 0.2mmol), 5,8-dibromo -2,3-Dimethyl-6,7-bis(n-octyloxy)quinoxaline (114mg, 0.2mmol) was added into a flask containing 10ml of toluene solvent, and potassium carbonate (2mL, 2mol / L) The solution was added to the flask, vacuumed to remove oxygen and filled with argon, then bistriphenylphosphinepalladium dichloride (5.6mg, 0.008mmol) was added; the flask was heated to 100°C for Suzuki coupling reaction for 48h. Then , stop the polymerization reaction after coo...

Embodiment 2

[0035] Example 2: The quinoxaline-based copolymer of this example, that is, poly{2,2'-(9,10-bis(methoxy)phenanthrene-2,7-diyl-co-5,8-di Base-2,3-dimethyl-6,7-di(n-eicosyloxy)quinoxaline} (P2), (where R1 is methyl, R2 is n-eicosyl, n=17 ), its structural formula is as follows:

[0036]

[0037] The preparation steps of above-mentioned polymer are as follows:

[0038] The reaction formula is as follows:

[0039]

[0040] Under the protection of a mixed gas of nitrogen and argon, 2,2'-(9,10-di(methoxy)phenanthrene-2,7-dipinacol borate (147mg, 0.3mmol), 5,8- Add dibromo-2,3-dimethyl-6,7-bis(n-eicosyloxy)quinoxaline (273mg, 0.3mmol) and 15mL tetrahydrofuran into a 50mL two-necked bottle, fully dissolve and pass nitrogen gas After exhausting the mixed gas with argon for about 20 minutes, add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) into it, fully dissolve and then add sodium bicarbonate (3mL, 2mol / L) solution. After exhausting the mixed gas with argon for abou...

Embodiment 3

[0042]Example 3: The quinoxaline-based copolymer of this example, namely poly{2,2'-(9,10-bis(n-eicosyloxy)phenanthrene-2,7-diyl-co-5, 8-diyl-2,3-dimethyl-6,7-di(methoxy)quinoxaline} (P3), (where R1 is n-eicosyl, R2 is methyl, n=85 ), whose structure 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 nitrogen protection, 2,2'-(9,10-di(n-eicosyloxy)phenanthrene-2,7-dipinacol borate (307mg, 0.3mmol), 5,8-dibromo -2,3-Dimethyl-6,7-di(methoxy)quinoxaline (124mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and tris(o-methylphenyl)phosphine (21mg , 0.06mmol) was added into a flask filled with 12mL of N,N-dimethylformamide, fully dissolved, and potassium carbonate (3mL, 2mol / L) solution was added, and then the flask was vented with nitrogen for about 30min; The flask was heated to 130°C for Suzuki coupling reaction for 12h. After cooling down, the polymeriz...

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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 R1 and R2 individually represent a C1-C20 alkyl group and the n represents an integer in a range of 17 to 85. 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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Patent Type & Authority Applications(China)
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