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Fluorene copolymer containing thiophene and thiophene pyrrole diketone unit and its preparation method and application

A technology of thiophene pyrrole diketone and thiophene units, which is applied in the field of copolymers, can solve the problems of low photoelectric conversion efficiency, achieve the effects of improving photoelectric conversion efficiency, simple structure, and expanding the absorption range

Inactive Publication Date: 2011-12-28
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells

Method used

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  • Fluorene copolymer containing thiophene and thiophene pyrrole diketone unit and its preparation method and application
  • Fluorene copolymer containing thiophene and thiophene pyrrole diketone unit and its preparation method and application
  • Fluorene copolymer containing thiophene and thiophene pyrrole diketone unit and its preparation method and application

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preparation example Construction

[0039] The present invention also provides a method for preparing a fluorene copolymer containing thiophene and thiophenepyrrole diketo units, comprising the following steps:

[0040] Provide Fluorene Monomer B 1 , thiophene monomer B 2 , Thiophenepyrrole diketomonomer B 3 ;

[0041]

[0042] In an oxygen-free environment (the present invention uses nitrogen and / or an inert gas as a protective gas to form an oxygen-free environment), the B 1 , B 2 , B 3 Carry out Suzuki reaction under catalyst, alkali solution and first organic solvent at 65℃~120℃ with molar ratio of 1.0:c:d (wherein, c>0, d>0, 0.9≤c+d≤1.1) 24 ~72 hours, a solution of fluorene copolymer containing thiophene and thiophenepyrrole diketo units is obtained; the reaction formula is as follows:

[0043]

[0044] Wherein, the catalyst is a mixture of organic palladium or organic palladium and organic phosphorus ligands; the organic palladium is Pd(PPh 3 ) 4 , Pd 2 (dba) 3 or Pd(PPh 3 ) 2 Cl 2 ; The...

Embodiment 1

[0058] This embodiment discloses a fluorene copolymer with the following structure:

[0059]

[0060] In the formula: x+y=1, x≠0, y≠0; n is an integer between 1-200.

[0061] The preparation steps of the fluorene copolymer are as follows:

[0062] 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaboranyl)-9,9-dimethylfluorene:

[0063]

[0064] At -100°C, under nitrogen conditions, 20.00 mL of n-butyllithium solution with a concentration of 1.00 M was added to the reaction containing 3.52 g of 2,7-dibromo-9,9-dimethylfluorene and 100 mL of tetrahydrofuran After stirring for 2 hours, 4.17 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxolaborane was slowly added dropwise to the bottle, and returned to room temperature. Continue stirring for 24 hours; when the reaction is over, pour the reaction solution into water, extract with ether, dry over anhydrous magnesium sulfate, spin-evaporate, and separate by column chromatography to obtain 2,7-bis(4,4,5,5-tetramethyl...

Embodiment 2

[0079] This embodiment discloses a fluorene copolymer with the following structure:

[0080]

[0081] In the formula: x+y=1, x≠0, y≠0; n is an integer between 1-200.

[0082] The preparation steps of the fluorene copolymer are as follows:

[0083] 1. Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaboranyl)-9,9-dimethylfluorene: see the preparation steps for details Example 1.

[0084]

[0085] 2. Preparation of 3,6-dimethylthieno[3,2-b]thiophene:

[0086]

[0087] 12.00 g of 3,6-dibromo-thieno[3,2-b]thiophene and 132 mg of (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) chloride were added into a 100 mL glass vial equipped with a stir bar, sealed, and nitrogen purged. Add 30 mL of tetrahydrofuran and 50 mL of methylzinc bromide to form a 1.0 M molar solution in tetrahydrofuran; stir at room temperature for 30 minutes and heat in a microwave reactor at 140°C for 50 minutes. Cooled, diluted with methyl tert-butyl ether (MTBE, the same below), washed with di...

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Abstract

The invention belongs to the field of photoelectric materials, and discloses fluorene copolymer containing thiophene and thiophene-pyrrole dione units. The polymer is characterized by having a structural formula (I), wherein R1, R2 and R3 are hydrogen or C1-C20 alkyl groups; x+y is equal to 1; x is not equal to 0; y is not equal to 0; n is an integer of 1-200; and Ar is a thiophene unit-containing group. The invention also discloses a preparation method and application of the fluorene copolymer containing thiophene and thiophene-pyrrole dione units. Compared with the prior art, the alkyl group is introduced to improve the dissolubility and the molecular weight of a product, so that spin coating polymer or oligomer can be realized; the polymer consisting of monomers B1, B2 and B3 can form an extremely strong donor-receptor structure; on one hand, the stability of the material is favorably improved; on the other hand, the energy band gap of the material is favorably reduced; thus, the sunlight absorption range is expanded, and the photoelectric conversion efficiency is increased; and Suzuki reaction is an extremely mature polymerization reaction and has the advantages of high yield,mild conditions and easiness in control.

Description

technical field [0001] The present invention relates to a copolymer, in particular to a fluorene copolymer containing thiophene and thiophenepyrrole diketo units. [0002] The invention also relates to a preparation method and application of a fluorene copolymer containing thiophene and thiophenepyrrole dione units. Background technique [0003] Today's world economy is mainly based on fossil fuels such as coal, oil and natural gas. However, these non-renewable fossil energy sources are constantly being depleted. Since the beginning of the 21st century, the global energy problem and the consequent environmental pollution and climate warming have become increasingly prominent and aggravated. Solar energy is considered to be one of the most promising renewable energy sources due to its outstanding advantages such as widespread and broad distribution, large number of resources, no pollution, cleanliness, safety, and easy access. Solar cells directly convert sunlight energy i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54H01L51/30
CPCY02E10/549Y02E10/50
Inventor 周明杰黄杰刘辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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