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Anthraquinone based copolymer, preparation method and applications thereof

A copolymer, anthraquinone-based technology, 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, mismatched spectral response, etc., and achieves novel material structure and good electrical properties. Chemical properties, wide absorption effect

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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  • Anthraquinone based copolymer, preparation method and applications thereof
  • Anthraquinone based copolymer, preparation method and applications thereof
  • Anthraquinone based copolymer, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: The anthraquinone-based copolymer of this example, that is, poly{2,2'-(9-((5-n-octylthiophen-2-yl)methylene)-9H-fluorene-2,7 -diyl-co-2,6-diyl-1,5-bis(n-octyloxy)anthracene-9,10-dione} (wherein, R1 is n-octyl, R2 is n-octyl, n=46), 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 argon protection, 2,2'-(9-((5-n-octylthiophen-2-yl)methylene)-9H-fluorene-2,7-dipinacol borate (125mg ,0.2mmol), 2,6-dibromo-1,5-bis(n-octyloxy)anthracene-9,10-dione (124mg, 0.2mmol) was added into a flask filled with 10ml of toluene solvent, after fully dissolving Potassium carbonate (2mL, 2mol / L) solution was added to the flask, vacuum deoxygenated and filled with argon, then bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol) was added; the flask was heated to 100 ℃ for Suzuki coupling reaction for 48h. Subsequently, stop ...

Embodiment 2

[0035] Example 2: The anthraquinone-based copolymer of this example, that is, poly{2,2'-(9-((5-methylthiophen-2-yl)methylene)-9H-fluorene-2,7- Diyl-co-2,6-diyl-1,5-bis(n-eicosyloxy)anthracene-9,10-dione} (P2), (where R1 is methyl, R2 is di Decyl, n=84), 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 mixed gas of nitrogen and argon, 2,2'-(9-((5-methylthiophen-2-yl)methylene)-9H-fluorene-2,7-dipinacol borate (158mg, 0.3mmol), 2,6-dibromo-1,5-bis(n-eicosyloxy)anthracene-9,10-dione (287mg, 0.3mmol) and 15mL tetrahydrofuran were added to a 50mL two-necked bottle After fully dissolving, introduce 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 add sodium bicarbonate (3mL, 2mol / L) solution. After the mixed gas ...

Embodiment 3

[0042]Example 3: The anthraquinone-based copolymer of this example, that is, poly{2,2'-(9-((5-n-eicosylthiophen-2-yl)methylene)-9H-fluorene-2 ,7-diyl-co-2,6-diyl-1,5-dimethoxyanthracene-9,10-dione} (P3), (where R1 is n-eicosyl, R2 is methyl base, n=11), 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 nitrogen protection, 2,2'-(9-((5-n-eicosylthiophen-2-yl)methylene)-9H-fluorene-2,7-dipinacol borate (238mg , 0.3mmol), 2,6-dibromo-1,5-di(methoxy)anthracene-9,10-dione (141mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and three (o Methylphenyl)phosphine (21mg, 0.06mmol) was added to a flask containing 12mL of N,N-dimethylformamide, and after fully dissolving, potassium carbonate (3mL, 2mol / L) solution was added, and then poured into the flask After evacuating the air with nitrogen for about 30 minutes, heat the flask to 130 °...

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Abstract

The invention belongs to the field of organic solar cell materials, and discloses an anthraquinone based copolymer, a preparation method, and applications thereof. The structural formula of the copolymer is represented in the description, the R1 and R2 both represent a C1-C20 alkyl group, and the n is an integer in a range of 11 to 98. In the provided anthraquinone copolymer, the anthraquinone group contains a quinoid structure, which has an excellent fluorescent property and good electrochemical performance, and moreover, the phenyl ring is modified by alkyloxy so as to improve the solubility and film-forming ability of the copolymer. Fluorene is a compound with a rigid flat structure, and has a high thermal stability and fluorescence quantum yield. The provided anthraquinone based copolymer can be applied to solar cells so as to increase the light conversion rate of the organic solar cells.

Description

technical field [0001] The invention relates to the field of organic solar cell materials, in particular to an anthraquinone-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, 1...

Claims

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Application Information

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IPC IPC(8): C08G61/02H01L51/46
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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