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

A technology of benzotriazole and dithiophene, applied in the field of organic semiconductor materials, can solve problems such as low conversion efficiency, and achieve the effects of improved energy conversion efficiency, high electron mobility and novel structure

Inactive Publication Date: 2015-05-06
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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  • Dithienylbenzotriazole side chain-containing polymer, preparation method thereof, and organic solar cell device
  • Dithienylbenzotriazole side chain-containing polymer, preparation method thereof, and organic solar cell device
  • Dithienylbenzotriazole side chain-containing polymer, preparation method thereof, and organic solar cell device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The polymer containing dithiophene benzotriazole side chain in this example, that is, poly{6,6,12,12-tetra-n-octyl-2,8-diyl-6,12-dihydroindeno[ 1,2-b:1',2'-e]pyrazine-co-4-(2-(2,5-diylthiophen-3-yl)vinyl)-N-(4-(n-octyloxy Base) phenyl)-N-phenylaniline} (P1), (where R1 is n-octyl, R2 is n-octyl, n=58), its structural formula is as follows:

[0033]

[0034] The preparation steps of above-mentioned polymer are as follows:

[0035] The reaction formula is as follows:

[0036]

[0037] Under argon protection, 6,6,12,12-tetra-n-octyl-2,8-dipinacol borate-6,12-dihydroindeno[1,2-b:1' ,2'-e]pyrazine (191mg, 0.2mmol), 4-(2-(2,5-dibromothiophen-3-yl)vinyl)-N-(4-(n-octyloxy)benzene) -N-Phenylaniline (128mg, 0.2mmol) was added to a flask filled with 10ml of toluene solvent, and after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added to the flask, vacuumed to remove oxygen and filled with argon , and then added bistriphenylphosphinepalladium dichloride...

Embodiment 2

[0041] The polymer containing dithiophene benzotriazole side chain in this example, that is, poly{6,6,12,12-tetramethyl-2,8-diyl-6,12-dihydroindeno[1, 2-b:1',2'-e]pyrazine-co-4-(2-(2,5-diylthiophen-3-yl)ethenyl)-N-(4-(n-eicosyloxy Base) phenyl)-N-phenylaniline} (P2), (where R1 is methyl, R2 is n-eicosyl, n=12), its structural formula is as follows:

[0042]

[0043] The preparation steps of above-mentioned polymer are as follows:

[0044] The reaction formula is as follows:

[0045]

[0046]Under the protection of mixed gas of nitrogen and argon, 6,6,12,12-tetramethyl-2,8-dipinacol borate-6,12-dihydroindeno[1,2-b:1 ',2'-e]pyrazine (169mg, 0.3mmol), 4-(2-(2,5-dibromothiophen-3-yl)ethenyl)-N-(4-(n-eicosyloxy ) Benzene)-N-phenylaniline (242mg, 0.3mmol) and 15mL tetrahydrofuran were added into a 50mL two-necked bottle, and after fully dissolving, a mixture of nitrogen and argon was introduced to exhaust the air for about 20 minutes, and then tetratriphenyl Phosphine pall...

Embodiment 3

[0049] The polymer containing dithiophene benzotriazole side chain in this example, that is, poly{6,6,12,12-tetraeicosanyl-2,8-diyl-6,12-dihydroindeno [1,2-b:1',2'-e]pyrazine-co-4-(2-(2,5-diylthiophen-3-yl)ethenyl)-N-(4-(methoxy Base) phenyl)-N-phenylaniline} (P3), (where R1 is n-eicosyl, R2 is methyl, n=84), its structural formula is as follows:

[0050]

[0051] The preparation steps of above-mentioned polymer are as follows:

[0052] The reaction formula is as follows:

[0053]

[0054] Under nitrogen protection, 6,6,12,12-tetraeicosyl-2,8-dipinacol borate-6,12-dihydroindeno[1,2-b:1', 2'-e]pyrazine (488mg, 0.3mmol), 4-(2-(2,5-dibromothiophen-3-yl)vinyl)-N-(4-(methoxy)benzene)-N -Phenylaniline (179mg, 0.33mmol), palladium acetate (3.5mg, 0.015mmol) and three (o-methylphenyl) phosphine (21mg, 0.06mmol) were added to 12mL of N,N-dimethylformaldehyde In the flask of amide, add potassium carbonate (3mL, 2mol / L) solution after fully dissolving, then blow nitrogen into t...

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Abstract

The invention belongs to the field of organic semiconductors, and discloses a dithienylbenzotriazole side chain-containing polymer, a preparation method thereof, and an organic solar cell device. The structural general formula of the above host material is shown in the specification. In the formula, R1 and R2 respectively represent C1-C20 alkyl groups, and n is an integer in a range of 12-97. In the dithienylbenzotriazole side chain-containing polymer, triphenylamine is an excellent hole transport unit; and diindenopyrazine is a heterocyclic compound with a rigid planar structure, and has high heat stability and electron mobility. The above triphenylamine side chain-containing copolymer can be applied in solar cells in order to improve the phototransformation efficiency.

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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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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