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Benzothiadiazolyl containing polymer and preparation method and application thereof

A technology based on benzothiadiazolyl and polymers, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of low conversion efficiency, achieve reduced manufacturing costs, excellent photovoltaic performance, and simple synthesis The effect of the route

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

Research in this area has made rapid progress in recent years, but the conversion efficiency of organic polymer solar cells is still much lower than that of inorganic solar cells

Method used

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  • Benzothiadiazolyl containing polymer and preparation method and application thereof
  • Benzothiadiazolyl containing polymer and preparation method and application thereof
  • Benzothiadiazolyl containing polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The polymer containing benzothiadiazolyl group in this example, that is, poly{2,6-diyl-4,4-bis(n-octyl)cyclopentadithiophene-co--5,6-bis (n-octyloxy)-4,7-di(5-yl-thienyl)-2,1,3-benzothiadiazole} (P1), (where R1 is n-octyl, R2 is n- Octyl, n=59), 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, 2,6-bistrimethyltin-4,4-bis(n-octyloxy)cyclopentadithiophene (146 mg, 0.2 mmol), 5,6-bis(n-octyloxy base)-4,7-bis(5-bromothienyl)-2,1,3-benzothiadiazole (143mg, 0.2mmol) was added to a flask filled with 10ml of toluene solvent, vacuumed to remove oxygen and filled with Infuse argon, then add bistriphenylphosphinepalladium dichloride (5.6mg, 0.008mmol); heat the flask to 100°C for Stille coupling reaction for 36h. Subsequently, the polymerization reaction was stopped after cooling down, and 50 ml of methanol was add...

Embodiment 2

[0035] The benzothiadiazolyl-containing polymer of this example, that is, poly{2,6-diyl-4,4-dimethylcyclopentadithiophene-co-5,6-bis(n-2 Alkoxy)-4,7-di(5-yl-thienyl)-2,1,3-benzothiadiazole} (P2), (where R1 is methyl, R2 is n-eicosyl , n=100), 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, 2,6-ditrimethyltin-4,4-dimethylcyclopentadithiophene (218mg, 0.3mmol), 5,6-bis(n-eicosane Oxygen)-4,7-bis(5-bromothienyl)-2,1,3-benzothiadiazole (315mg, 0.3mmol) and 15mL tetrahydrofuran were added into a 50mL two-necked bottle, fully dissolved and passed After entering the mixed gas of nitrogen and argon and exhausting the air for about 20 minutes, then add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) into it, and then fully pass the mixed gas of nitrogen and argon to exhaust the air...

Embodiment 3

[0043] The benzothiadiazolyl-containing polymer in this example, namely poly{2,6-diyl-4,4-di(n-eicosyl)cyclopentadithiophene-co-5,6- Bis(methoxy)-4,7-bis(5-yl-thienyl)-2,1,3-benzothiadiazole} (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, 2,6-bistrimethyltin-4,4-bis(n-eicosyl)cyclopentadithiophene (319mg, 0.3mmol), 5,6-bis(methoxy) -4,7-bis(5-bromothienyl)-2,1,3-benzothiadiazole (171mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and three (o-methoxybenzene Base) 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 6h. 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 benzothiadiazolyl 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 benzothiadiazolyl containing polymer disclosed by the invention, benzothiadiazole is an important electron acceptor unit, and after bithiophene is introduced, the absorption range is widened and the bandgap becomes smaller; pentamethylene dithiophene (PDT) has easily-modified photophysical properties, and copolymers of PDT show excellent photovoltaic performance; by applying the polymer, which is prepared through copolymerizing benzothiadiazole and PDT 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 organic solar cell materials, in particular to a polymer containing benzothiadiazole 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. Organic semiconductor materials have attracted much attention for their advantages such as easy availability of raw materials, low price, simple process, strong 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 conjugated polymers and C 60 After the light-induced electron transfer phenomenon between organic polymer solar cells has gradually become a research hotspot. Research in this area has achieved rapid development in recent years, but the conversion efficiency of organic polymer solar cells is s...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00H01L51/46
CPCY02E10/549
Inventor 周明杰张振华王平钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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