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Donor-receptor type conjugated polymer containing dithiophen b pyrrole, preparation method and application thereof

A conjugated polymer, dithiophene technology, applied in semiconductor/solid-state device manufacturing, electrical solid-state devices, semiconductor devices, etc., can solve the problems of limited types of narrow-bandgap polymers, limited large-scale applications, and difficulty in the synthesis of PCPDTBT. The effect of high energy conversion efficiency, good planarity and simple preparation method

Inactive Publication Date: 2009-04-15
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the types of narrow-bandgap polymers that can be selected are currently limited, and the synthesis of PCPDTBT is relatively difficult, which limits its potential large-scale application.

Method used

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  • Donor-receptor type conjugated polymer containing dithiophen b pyrrole, preparation method and application thereof
  • Donor-receptor type conjugated polymer containing dithiophen b pyrrole, preparation method and application thereof
  • Donor-receptor type conjugated polymer containing dithiophen b pyrrole, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of N-substituted dithiophene[3,2-b:2',3'-d]pyrrole bismethyl tin salt monomer

[0039]

[0040] Referring to the method disclosed in Macromolecules., 2007, 40, 4173-4181, using 3,3'-dibromo-4,4'-disubstituted dithiophene and primary amine as raw materials, the compound containing Dithiopheno[3,2-b:2',3'-d]pyrroles with different substituents. Dithiophene[3,2-b:2',3'-d]pyrroles with different substituents were converted to dithiophene[3,2- b: 2',3'-d]pyrrole bismethyl tin salt monomer, yield 43%-92%.

[0041] Take the preparation of 2,6-ditrimethyltin-N-(1-pentylhexyl)dithiophene[3,2-b:2',3'-d]pyrrole as an example to illustrate in detail below, the synthesis steps are as follows :

[0042]

[0043] (1) N-(1-pentylhexyl)dithiophene[3,2-b:2',3'-d]pyrrole

[0044] 3,3'-Dibromobithiophene (2.43g, 7.50mmol), sodium tert-butoxide (1.73g, 18.0mmol), tris(dibenzylideneacetone)dipalladium (Pd 2 dba 3 , 0.172g, 0.190mmol) and 2,2'-bis(diphenylph...

Embodiment 2

[0047] Example 2: Preparation of 4,7-bisthienyl-2,1,3-benzothiadiazole

[0048]

[0049] Referring to the method disclosed in J.Mater.Chem., 2002, 12, 2887-2892, using 2-bromo-3,4-disubstituted thiophene as a raw material, debromination with butyllithium at -78°C and then adding Tributyltin chloride to obtain thiophene monotin salt, react it with 4,7-dibromobenzothiadiazole through Stille reaction to obtain bisthienyl-substituted benzothiadiazole, and then use NBS for bromination to obtain Dibromo-substituted Ar acceptor unit, yield 30-35%.

[0050] Below take the preparation of 4,7-bis(5-bromo-2-thiophene)-2,1,3-benzothiadiazole as an example to be specifically described, and the synthesis steps are as follows:

[0051]

[0052] (1) Tributyl-2-thienstannane

[0053] Add 2-bromothiophene (6.11 g, 37.5 mmol) into the reaction flask, and then add 100 mL of tetrahydrofuran. Cool down to -78°C, add n-butyllithium solution (16.5 mL, 41.2 mmol, 2.5M hexane solution) dropwis...

Embodiment 3

[0058] Example 3: Preparation of 2,3-disubstituted-5,7-dibromothieno[3,4-b]pyrazine

[0059]

[0060] Referring to the method disclosed in J.Org.Chem., 2002, 67, 9073-9076, using 2,5-dibromo-3,4-dinitrothiophene as a raw material, first reduce it to 3 with tin powder , 4-diaminothiophene, and then react with substituted glyoxal to obtain 2,3-disubstituted thieno[3,4-b]pyrazine, and finally use NBS bromination to obtain 2,3-disubstituted-5, 7-dibromothieno[3,4-b]pyrazine monomer, the yield is 70-90%.

[0061] Below take the preparation of 5,7-dibromothieno[3,4-b]pyrazine as an example to be specifically described, and the synthesis steps are as follows:

[0062]

[0063] (1) 3,4-diaminothiophene

[0064] Add 2,5-dibromo-3,4-dinitrothiophene (3.00g, 9.04mmol) and 54mL concentrated hydrochloric acid into the reaction flask, add ice bath to cool, slowly add tin powder (7.48g, 63.0mmol) to make the reaction The temperature of the material is maintained at 25-30°C, and the ...

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Abstract

The invention relates to a donor-recipient typed conjugated polymer containing two thiofuran and pyrrole and the preparation method and applications thereof. Using a construction mode of donor-recipient typed co polymerization for preparing the conjugated polymer can absorb action spectrum, cover UV-Visible and near infrared region to fully use sunlight. The donor uses a constitution unit of two thiofuran and pyrrole with a good plane performance, high density of electron cloud and easy preparation. The preparation of the conjugated polymer is easy, with absorbing spectrum in the UV-Visible and near infrared region of 300 to1000nm and the energy transforming efficiency being 3 percent. The performances of prepared solar batteries are respectively: white light (light intensity of 100mW / cm<2> ) irradiating, the open-circuit voltage is equal to 0.37 to 0.54 V; the short circuit current is equal to 6.69 to 13.8mA / cm<2>; the packing factor is equal to 0.35 to 0.44; and the efficiency of energy transformation is equal to 1 to 3 percent.

Description

technical field [0001] The invention relates to a donor-acceptor conjugated polymer containing dithienopyrrole, a preparation method thereof, and an application thereof in preparing solar cells. Background technique [0002] In recent years, with the further depletion of fossil energy and the soaring price, more and more countries have turned their attention to solar energy, a clean and pollution-free renewable energy. How to effectively use solar energy is a difficult problem facing scientists from all over the world. At present, silicon-based and other inorganic metal compound solar cells are the mainstream in this research field, especially amorphous silicon thin-film solar cells. Stability is constantly improving. However, due to the limitations of materials and processing technology, the cost of amorphous silicon solar cells has been high, thus limiting its large-scale replacement of traditional fossil energy. Polymer solar cells have aroused great interest in academi...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCC09B69/109C09B57/08C09B5/62C09B69/102Y02E10/50H01L51/0053Y02E10/549H10K85/621
Inventor 耿延候岳威
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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