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Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device

A technology of benzotriazole and dithiophene, which is applied in the field of organic semiconductor materials, can solve the problems of low conversion efficiency and achieve the effects of improved energy conversion efficiency, novel structure and reduced process flow

Inactive Publication Date: 2015-04-29
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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  • Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device
  • Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device
  • Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The polymer containing dithiophene benzotriazole side chain in this embodiment, that is, poly{2,6-diyl-4,4-di(n-octyl)cyclopentadithiophene-co-4-(5 -(2-(2,5-diylthiophene)vinyl)thiophen-2-yl)-2-n-octyl-7-(thiophen-2-yl)-2H-benzo[d][1,2 ,3] Triazole} (P1), (where R1 is n-octyl, R2 is n-octyl, n=57), its structural formula is as follows:

[0032]

[0033] The preparation steps of above-mentioned polymer are as follows:

[0034] The reaction formula is as follows:

[0035]

[0036] Under argon protection, 2,6-ditrimethyltin-4,4-bis(n-octyloxy)cyclopentadithiophene (146mg, 0.2mmol), 4-(5-(2-( 2,5-Dibromothiophene)vinyl)thiophen-2-yl)-2-n-octyl-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole (132mg, 0.2mmol) was added to a flask containing 10ml of toluene solvent, vacuumed to remove oxygen and filled with argon, then added bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol); the flask was heated to 100 ℃ for Stille coupling reaction 36h. Subsequently, the p...

Embodiment 2

[0040] The polymer containing dithiophene benzotriazole side chain in this embodiment, that is, poly{2,6-diyl-4,4-di(methyl)cyclopentadithiophene-co-4-(5- (2-(2,5-diylthiophene)vinyl)thiophen-2-yl)-2-n-eicosyl-7-(thiophen-2-yl)-2H-benzo[d][1, 2,3] Triazole} (P2), (where R1 is methyl, R2 is n-eicosyl, n=41), its structural formula is as follows:

[0041]

[0042] The preparation steps of above-mentioned polymer are as follows:

[0043] The reaction formula is as follows:

[0044]

[0045]Under the protection of mixed gas of nitrogen and argon, 2,6-ditrimethyltin-4,4-dimethylcyclopentadithiophene (218mg, 0.3mmol), 4-(5-(2-(2 ,5-Dibromothiophene)vinyl)thiophen-2-yl)-2-n-eicosyl-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]tri Add oxazole (249mg, 0.3mmol) and 15mL tetrahydrofuran into a 50mL two-neck bottle, fully dissolve, pass in a mixture of nitrogen and argon to exhaust the air for about 20min, and then add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) Add it, and the...

Embodiment 3

[0048] The polymer containing dithiophene benzotriazole side chains in this example, that is, poly{2,6-diyl-4,4-di(n-eicosyl)cyclopentadithiophene-co-4- (5-(2-(2,5-diylthiophene)vinyl)thiophen-2-yl)-2-methyl-7-(thiophen-2-yl)-2H-benzo[d][1, 2,3] Triazole} (P3), (where R1 is n-eicosyl, R2 is methyl, n=10), its structural formula is as follows:

[0049]

[0050] The preparation steps of above-mentioned polymer are as follows:

[0051] The reaction formula is as follows:

[0052]

[0053] Under nitrogen protection, 2,6-ditrimethyltin-4,4-bis(n-eicosyl)cyclopentadithiophene (319mg, 0.3mmol), 4-(5-(2-(2 ,5-Dibromothiophene)vinyl)thiophen-2-yl)-2-methyl-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole (186mg , 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and tri(o-methylphenyl)phosphine (21mg, 0.06mmol) were added to the flask containing 12mL of N,N-dimethylformamide, followed by After passing nitrogen into the flask and exhausting the air for about 20 minutes, the flask wa...

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Abstract

The invention belongs to the field of organic semiconductors and discloses a dithienyl benzotriazole side chain-containing polymer, a preparation method thereof and an organic solar cell device. A main body material has a structural general 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 dithienyl benzotriazole side chain-containing polymer disclosed by the invention, a dithienyl benzotriazole (BTz) side chain is an important electron acceptor unit and is beneficial to the reduction of a band gap of the polymer; cyclopentano-dithiophene (PDT) has easily-modified photophysical properties, and copolymers of PDT show the advantages of relatively high absorption coefficient and relatively wide absorption range to sunlight, and the like; by applying the polymer, which is prepared through copolymerizing BTz and PDT by a Stille coupling method, to solar cells, the efficiency of organic electroluminescent devices can be increased.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to a polymer containing dithiophene benzotriazole side chains and a preparation method thereof. The invention also relates to an organic solar cell device using the polymer containing dithiophene benzotriazole side chains as an electron donor material for an active layer. 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 ph...

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 周明杰张振华王平钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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