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Crosslinking thiopheno[3,4-b] thiophene conjugated polymer and preparation method and application thereof

A technology of conjugated polymers and thiophene, which is applied in a class of crosslinkable thieno[3,4-b]thiophene conjugated polymers and its preparation and application fields, which can solve the problem of device performance degradation and device thermal stability Poor, unable to prepare multi-layer structure devices and other problems, to achieve the effect of improving thermal stability and solvent resistance

Active Publication Date: 2012-07-04
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
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AI Technical Summary

Problems solved by technology

One is that the formed film does not have solvent resistance. The existing conjugated polymer donor materials and fullerene and its derivative acceptor materials are easily soluble in organic solvents such as o-dichlorobenzene and chloroform. When preparing In the case of a multilayer film, the lower film will be dissolved by the solvent of the upper layer solution, so it is impossible to prepare a multilayer structure device
The second is that the thermal stability of the device is poor. The main reason is that the polymer, fullerene and its derivatives in the blend film tend to separate separately, so the formed nano-microphase separation structure is thermally unstable, and it will be in the device. Gradual changes during operation, resulting in degraded device performance

Method used

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  • Crosslinking thiopheno[3,4-b] thiophene conjugated polymer and preparation method and application thereof
  • Crosslinking thiopheno[3,4-b] thiophene conjugated polymer and preparation method and application thereof
  • Crosslinking thiopheno[3,4-b] thiophene conjugated polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1, prepare the conjugated polymer 1 of formula 1 structure

[0046] The conjugated polymer 1 of formula 1 is thieno[3,4-b]thiophene with bromine crosslinking group at the end of the alkyl chain and thieno[3,4-b]thiophene without bromine crosslinking group And [4,8-two (isooctyloxy) benzo [1,2-b:4,5-b '] terpolymer of dithiophene, its specific reaction formula is as follows:

[0047]

[0048] Formula 1

[0049] The specific preparation method is as follows:

[0050] Step 1) Mix 0.1mol of 1,8-octanediol with 0.18mol of hydrobromic acid, use toluene as solvent, stir and react at 110°C for 36 hours, extract, and distill under reduced pressure to obtain a colorless liquid which is 8-bromo-1- octanol.

[0051] Step 2) 8-bromo-1-octanol 12mmol, 4,6-dibromothieno[3,4-b]thiophene-2-carboxylic acid 3mmol, 1,3-dicyclohexylcarbodiimide 3.6mmol and Dimethylaminopyridine 1.05mmol mixed, anhydrous dichloromethane as solvent, nitrogen protection, stirring and reactin...

Embodiment 2

[0057] Embodiment 2, prepare the conjugated polymer 2 of formula 2 structure

[0058] The conjugated polymer 2 of formula 2 is thieno[3,4-b]thiophene with bromine crosslinking group at the end of the alkyl chain and thieno[3,4-b]thiophene without bromine crosslinking group And [4,8-two (isooctyloxy) benzo [1,2-b:4,5-b '] terpolymer of dithiophene, its specific reaction formula is as follows:

[0059]

[0060]

[0061] (Formula 2)

[0062] The specific preparation method is as follows:

[0063] Step 1) Mix 0.1mol of 1,8-octanediol with 0.18mol of hydrobromic acid, use toluene as solvent, stir and react at 110°C for 36 hours, extract, and distill under reduced pressure to obtain a colorless liquid which is 8-bromo-1- octanol.

[0064] Step 2) 8-bromo-1-octanol 12mmol, 4,6-dibromothieno[3,4-b]thiophene-2-carboxylic acid 3mmol, 1,3-dicyclohexylcarbodiimide 3.6mmol and Dimethylaminopyridine 1.05mmol mixed, anhydrous dichloromethane as solvent, nitrogen protection, stirrin...

Embodiment 3

[0070] The solvent resistance experiment of the conjugated polymer 1 prepared by embodiment 3, embodiment 1

[0071] Step 1) Prepare 4 glass slides of 10mm×10mm, wash them twice with detergent water, secondary water, acetone, and ethanol successively, and dry them.

[0072] Step 2) The glass slide was treated with ultraviolet ozone for 20 minutes, and 50 microliters of poly(3,4-ethylenedioxythiophene) (PEDOT:PSS) solution was spin-coated on the surface of the glass slide.

[0073] Step 3) Spin-coat 20 microliters of a 10 mg / ml solution of conjugated polymer 1 prepared in Example 1 on a film of poly(3,4-ethylenedioxythiophene) (PEDOT:PSS).

[0074] Step 4) Put the four slides coated with the film under the wavelength of 254nm of ultraviolet lamp, and irradiate them for 0, 5, 10, 20 minutes respectively, and measure the absorption of the film.

[0075] Step 5) Immerse the glass slide in the o-dichlorobenzene solvent for 5 minutes, take it out, rinse it with acetone for 30 secon...

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Abstract

The invention discloses a crosslinking thiopheno[3,4-b] thiophene conjugated polymer and a preparation method and application thereof. The constitutional formula of the conjugated polymer is as formula I, R1 is a functional group capable of conducting crosslink under the condition that ultraviolet illumination, heating or initiators exist. R2 is a functional group capable of conducting crosslink under the condition that ultraviolet illumination, heating or initiators exist or a substituent group which is different from R1 and is not crosslinked. Arl and Ar2 are units which are identical or different and have conjugated characteristics. X1 and X2 are both selected from the following perssad: H, F, Cl, Br, cyan and ester groups. a / (a+b) is any one of number from 0 to 1, and the a / (a+b) is not zero. n represents repeated number of main polymer chain units, and the value of n is a natural number equal to and larger than 4. The polymer has narrower band gaps, improves anti-solvent performance by crosslinking and has wide application prospect in photoelectric function devices, especially the field of polymer solar batteries.

Description

technical field [0001] The invention relates to a class of crosslinkable thieno[3,4-b]thiophene conjugated polymers, a preparation method and application thereof. Background technique [0002] Due to its low cost, light weight, and easy preparation of large-area flexible devices, polymer solar cells have aroused widespread interest among researchers in today's increasingly aggravated energy crisis, and with the efforts of many scientific researchers, High-efficiency polymer materials continue to emerge, and the highest energy conversion efficiency has reached 7-8%. (1) Chen, H.Y.; Hou, J.H.; Zhang, S.Q.; Liang, Y.Y.; (2) Samuel C. Price; Andrew C. Stuart; Yang. L. Q.; Zhou. H. X.; (3) Lijun Huo, Shaoqing Zhang, Xia Guo, Feng Xu, Yongfang Li, and Jianhui Hou Angew. Chem. Int. Ed. 2011, 50, 9697-9702; (4) Samuel C. Price, Andrew C. Stuart, Liqiang Yang, Huaxing Zhou, Wei You, J.Am.Chem.Soc.2011, 133, 4625-4631; (5) Ta-Ya Chu, Jianping Lu, Serge Beaupre, Yangguang Zhang, Jea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549Y02P70/50
Inventor 侯剑辉钱德平
Owner INST OF CHEM CHINESE ACAD OF SCI
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