Preparation methods for fluorine-containing thienopyrrolodione monomer and copolymer thereof

A technology of diketopyrrole and copolymer, which is applied in the field of preparation of fluorine-containing diketopyrrole monomer and its copolymer, can solve the problems of poor thermal stability and insufficient light absorption range, and achieve improved thermal stability, Effects of improving life and reducing energy gap

Inactive Publication Date: 2014-04-02
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] One of the purposes of the present invention is to provide a kind of good thermal stability, wide absorption range and the defect that the thermal stability of D-A narrow bandgap copolymer based on TPD and BDT is poor in the prior art, and the visible light absorption range is not wide enough. Fluorine-containing thienopyrrole diketone monomers with strong absorbance and excellent charge transport properties and their copolymers with benzodithiophene derivatives

Method used

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  • Preparation methods for fluorine-containing thienopyrrolodione monomer and copolymer thereof
  • Preparation methods for fluorine-containing thienopyrrolodione monomer and copolymer thereof
  • Preparation methods for fluorine-containing thienopyrrolodione monomer and copolymer thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Preparation of fluorine-containing thienopyrrole diketone monomer

[0050] Mix (1 g, 5.8 mmol) 3,4-thiophenedicarboxylic acid and 10 ml thionyl chloride in an oxygen-free environment filled with inert gas, react at 100°C for 1 hour, cool to room temperature, and distill under reduced pressure The crude product 3,4-thiophenedicarboxylic acid chloride was obtained.

[0051] In an oxygen-free environment filled with inert gas, the obtained crude product 3,4-thiophenedicarboxylic acid chloride and anhydrous toluene were dissolved by heating, and slowly dropped into a solution of pentafluoroaniline (1.17 g, 6.38 mmol) in 3.5 ml of toluene, in Reacted at 120°C for 1 hour, cooled to room temperature, rotary evaporated, extracted, washed, and purified by column chromatography to obtain white crystal pentafluorophenyl-4 H - Thieno[3,4-c]pyrrole 4,6-(5 H ) diketone 0.86g.

[0052] Take (0.408 g, 1.27 mmol) of pentafluorophenyl-4 H - Thieno[3,4-c]pyrrole 4,6-(5 H ) diketone w...

Embodiment 2

[0054] Preparation of fluorine-containing thienopyrrole diketone monomer

[0055] Mix (2 g, 11.6 mmol) 3,4-thiophenedicarboxylic acid and 30 ml thionyl chloride in an oxygen-free environment filled with inert gas, react at 10°C for 7 h, cool to room temperature, and distill under reduced pressure to obtain Crude product 3,4-thiophenedicarboxylic acid chloride.

[0056] In an oxygen-free environment filled with inert gas, the obtained crude product 3,4-thiophenedicarboxylic acid chloride and anhydrous toluene were dissolved by heating, and slowly dropped into 180 mL of toluene solution of pentafluoroaniline (6.35 g, 34.8 mmol), in Reacted at 10°C for 14 hours, cooled to room temperature, rotary steamed, extracted, washed, and purified by column chromatography to obtain white crystal pentafluorophenyl-4 H - Thieno[3,4-c]pyrrole 4,6-(5 H ) diketone 1.96 g.

[0057] Take (1.2 g, 3.76 mmol) of pentafluorophenyl-4 H - Thieno[3,4-c]pyrrole 4,6-(5 H ) diketone was added to 40 mL ...

Embodiment 3

[0059] Preparation of fluorine-containing thienopyrrole diketone monomer

[0060] Mix (1.2g, 7.0 mmol) 3,4-thiophenedicarboxylic acid and 10ml thionyl chloride in an oxygen-free environment filled with inert gas, react at 50°C for 14 hours, cool to room temperature, and distill under reduced pressure to obtain Crude product 3,4-thiophenedicarboxylic acid chloride.

[0061] In an oxygen-free environment filled with inert gas, heat and dissolve the obtained crude product 3,4-thiophenedicarboxylic acid chloride and anhydrous toluene, slowly drop into (1.8 g, 10 mmol) pentafluoroaniline toluene solution, at 75 ° C Reaction at room temperature for 7 hours, cooled to room temperature, rotary evaporation, extraction, washing, purification by column chromatography to obtain white crystal pentafluorophenyl-4 H - Thieno[3,4-c]pyrrole 4,6-(5 H ) diketone 1.12 g.

[0062] Take (1.0 g, 3.13 mmol) of pentafluorophenyl-4 H - Thieno[3,4-c]pyrrole 4,6-(5 H ) diketone was added to 16 mL of...

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Abstract

The invention relates to preparation methods for a fluorine-containing thienopyrrolodione monomer and a copolymer thereof. According to the invention, thiophene-3,4-dicarboxylic acid is mixed with thionyl chloride, and then an organic solvent and a methylbenzene solution containing pentafluoroaniline are added so as to obtain a white crystal pentafluorophenyl-4H-thieno[3,4-c]pyrrolo-4,6-(5H)dione; then mixed liquor of N-bromo-succinimide, trifluoroacetic acid and concentrated H2SO4 is added so as to obtain a fluorine-containing thienopyrrolodione-benzodithiophene-pentafluorophenyl-4H-thieno[3,4-c]pyrrolo-4,6-(5H)dione bromide monomer; a benzodithiophene derivative monomer and the fluorine-containing thienopyrrolodione monomer are mixed, and a catalyst and an organic solvent are added so as to obtain the fluorine-containing thienopyrrolodione-benzodithiophene copolymer. Compared with the prior art, the invention has the following advantages: the utilization rate of sunlight, carrier mobility and thermal stability of the copolymer can be effectively improved, and the life of a device can be prolonged.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a preparation method of fluorine-containing thienopyrrole diketone monomer and a copolymer thereof. technical background [0002] Polymer Solar Cells (PSCs) overcome the disadvantages of silicon and inorganic semiconductor solar cells such as high cost, difficult flexible processing, and high toxicity. At the same time, they also have unique advantages such as portability, environmental friendliness, simple process, and large-scale production and processing. Therefore, polymer solar cell technology is expected to solve the increasingly serious energy crisis and environmental crisis to a large extent, and it is a new type of organic solar cell. To realize the commercialization of polymer solar cells, the energy conversion efficiency value should reach more than 10% and require a high service life. Therefore, the development of polymer solar cells with high p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D495/04C07D519/00H01L51/46
CPCY02E10/549
Inventor 凌启淡王文周铭露孙敏敏梁露英
Owner FUJIAN NORMAL UNIV
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