Anthraquinone based copolymer, preparation method, and applications thereof

A copolymer and anthraquinone-based 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, mismatched spectral response, etc., and achieves good electrochemical performance and structure. Novel, 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′-(9,10-bis(n-octyloxy)phenanthrene-2,7-diyl-co-2,6-bis Base-1,5-bis(n-octyloxy)anthracene-9,10-dione} (where R1 is n-octyl, R2 is n-octyl, n=51), 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′-(9,10-bis(n-octyloxy)phenanthrene-2,7-dipinacol borate (137mg, 0.2mmol), 2,6-dibromo -1,5-bis(n-octyloxy)anthracene-9,10-dione (124mg, 0.2mmol) was added to a flask filled with 10ml of toluene solvent, and potassium carbonate (2mL, 2mol / L) solution was dissolved fully Added to the flask, vacuumed to remove oxygen and filled with argon, then added bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol); the flask was heated to 100°C for Suzuki coupling reaction for 48h. Subsequently, after cooling Stop the polymerization reac...

Embodiment 2

[0035] Example 2: The anthraquinone-based copolymer of this example, that is, poly{2,2′-(9,10-bis(methoxy)phenanthrene-2,7-diyl-co-2,6-diyl -1,5-di(n-eicosyloxy)anthracene-9,10-dione} (P2), (where R1 is methyl, R2 is n-eicosyl, n=87), its structural formula 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′-(9,10-di(methoxy)phenanthrene-2,7-dipinacol borate (147mg, 0.3mmol), 2,6- Add dibromo-1,5-bis(n-eicosyloxy)anthracene-9,10-dione (287mg, 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 (4mg, 0.003mmol) was added into it, and after fully dissolving, sodium bicarbonate (3mL, 2mol / L) solution was added. Nitrogen and argon were fully ventilated After...

Embodiment 3

[0042] Example 3: The anthraquinone-based copolymer of this example, that is, poly{2,2′-(9,10-bis(n-eicosyloxy)phenanthrene-2,7-diyl-co-2,6 -Diyl-1,5-dimethoxyanthracene-9,10-dione} (P3), (where R1 is n-eicosyl, R2 is methyl, n=15), 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′-(9,10-bis(n-eicosyloxy)phenanthrene-2,7-dipinacol borate (307mg, 0.3mmol), 2,6-dibromo -1,5-bis(methoxy)anthracene-9,10-dione (141mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and tris(o-methylphenyl)phosphine (21mg, 0.06mmol ) into a flask containing 12mL of N,N-dimethylformamide, fully dissolved and then adding potassium carbonate (3mL, 2mol / L) solution, and then blowing nitrogen into the flask and exhausting the air for about 30min; the flask was heated Carry out Suzuki coupling reaction at 130°C for 12h. Then, stop the ...

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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, in the formula the R1 and R2 both represent a C1-C20 alkyl group, and n is an integer in a range of 15 to 92. In the provided anthraquinone based copolymer, the anthraquinone group contains a quinone structure, which has an excellent fluorescent property and good electrochemical performance, and moreover, the phenyl ring is modified by an alkoxy group so as to improve the solubility and film-forming ability of the polymer. Phenanthrene is a compound with a large planar rigid structure and has high thermal stability and fluorescence quantum yield. The light conversion rate of organic solar cells can be improved by applying the provided anthraquinone based copolymer to 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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Patent Type & Authority Applications(China)
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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