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Thienothienyl containing polymer and preparation method and application thereof

A polymer and thiophene-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 achieve excellent photovoltaic performance and simple synthesis route , the effect of wide absorption range

Inactive Publication Date: 2014-09-03
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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  • Thienothienyl containing polymer and preparation method and application thereof
  • Thienothienyl containing polymer and preparation method and application thereof
  • Thienothienyl containing polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The thienothienyl-containing polymer of this example, that is, poly{2,7-diyl-4,9-di(n-octyloxy)naphthodithiophene-co-2-n-octylsulfonyl-4 ,6-di(thiophen-2-yl)thieno[3,4-b]thiophene-2,6-diyl} (P1), (where R1 is n-octyl, R2 is n-octyl, n=65), 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 argon protection, 2,7-ditrimethyltin-4,9-bis(n-octyloxy)naphthodithiophene (164 mg, 0.2 mmol), 2,6-dibromo-2-n-octyl Sulfonyl-4,6-bis(thiophen-2-yl)thieno[3,4-b]thiophene (128mg, 0.2mmol) was added to a flask containing 10ml of toluene solvent, vacuumed to remove oxygen and filled with argon gas, and then added bistriphenylphosphine palladium 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 ...

Embodiment 2

[0035] The polymer containing thienothiophene group in this example, that is, poly{2,7-diyl-4,9-di(methoxy)naphthodithiophene-co-2-n-eicosylsulfonyl- 4,6-di(thiophen-2-yl)thieno[3,4-b]thiophene-2,6-diyl} (P2), (where R1 is methyl, R2 is n-eicosyl, n=34), 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, 2,7-ditrimethyltin-4,9-di(methoxy)naphthodithiophene (188mg, 0.3mmol), 2,6-dibromo-2- Add n-eicosylsulfonyl-4,6-bis(thiophen-2-yl)thieno[3,4-b]thiophene (242mg, 0.3mmol) and 15mL tetrahydrofuran into a 50mL two-necked bottle, after fully dissolving Infuse the mixed gas of nitrogen and argon to exhaust the air for about 20 minutes, then add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) into it, and then fully flow the mixed gas of nitrogen and argon to exhaust the air for ab...

Embodiment 3

[0043]The polymer containing thienothiophene group in this example, that is, poly{2,7-diyl-4,9-bis(n-eicosyloxy)naphthodithiophene-co-2-methylsulfonyl- 4,6-bis(thiophen-2-yl)thieno[3,4-b]thiophene-2,6-diyl} (P3), (where R1 is n-eicosyl, R2 is methyl, n=10), its structural formula is as follows:

[0044]

[0045] The preparation steps of above-mentioned polymer are as follows:

[0046] The reaction formula is as follows:

[0047]

[0048] Under nitrogen protection, 2,7-ditrimethyltin-4,9-bis(n-eicosyloxy)naphthodithiophene (348mg, 0.3mmol), 2,6-dibromo-2-methyl Sulfonyl-4,6-bis(thiophen-2-yl)thieno[3,4-b]thiophene (178 mg, 0.33 mmol), palladium acetate (3.5 mg, 0.015 mmol) and tris(o-methoxyphenyl ) Phosphine (21mg, 0.06mmol) was added to a flask containing 12mL of N,N-dimethylformamide, and then the flask was purged with nitrogen for about 20min; the flask was heated to 130°C for Stille coupling reaction for 6h . Subsequently, stop the polymerization reaction after ...

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Abstract

The invention belongs to the field of organic solar cell materials and discloses a thienothienyl containing polymer and a preparation method and application thereof. The polymer has a following structural formula shown in descriptions, wherein each of R1 and R2 is C1-C20 alkyl, and n is an integer between 10 and 100. According to the thienothienyl containing polymer disclosed by the invention, a relatively big electron withdrawing sulfonyl group is connected to thienothienyl (PTPT) and is an important electron acceptor unit, and after being modified with bithiophene, the polymer has the advantages of relatively narrow bandgap, relatively high sunlight absorption coefficient, relatively wide sunlight absorption range and the like; naphtho-dithiophene has easily-modified photophysical properties, and copolymers of naphtho-dithiophene show excellent photovoltaic performance; by applying the polymer, which is prepared through copolymerizing the PTPT and naphtho-dithiophene by a Stille coupling method, to solar cells, the problem of low efficiency of organic electroluminescent devices can be solved.

Description

technical field [0001] The invention relates to an organic solar cell material, in particular to a polymer containing thienothiophene group and its 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 con...

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 周明杰张振华王平黄辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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