Dibenzothiophene copolymer containing diazosulfide unit as well as preparation method and application of dibenzothiophene copolymer

A technology of benzodithiophene and benzothiadiazole, which is applied in the field of benzodithiophene copolymer and its preparation, can solve the problems of low photoelectric conversion efficiency and the like, and achieves improved carrier mobility, high yield, mild conditions

Inactive Publication Date: 2014-03-26
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the energy conversion efficiency of organic solar cells has been greatly improved, 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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  • Dibenzothiophene copolymer containing diazosulfide unit as well as preparation method and application of dibenzothiophene copolymer
  • Dibenzothiophene copolymer containing diazosulfide unit as well as preparation method and application of dibenzothiophene copolymer
  • Dibenzothiophene copolymer containing diazosulfide unit as well as preparation method and application of dibenzothiophene copolymer

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preparation example Construction

[0032] The preparation method of the above-mentioned benzodithiophene copolymer containing benzothiadiazole unit comprises the following steps:

[0033] S1, the structural formula is Compound A (that is, thiophene acetic acid derivatives, for R 1 , R 2 The difference of the substituent, the chemical nomenclature in each embodiment will be different, see each embodiment for details) use dichloromethane (CH 2 Cl 2 ) after dissolving, a mixed solution was obtained, and in an oxygen-free environment (at least one of nitrogen and argon exists), the mixed solution was added dropwise to 1,3-dicyclohexylcarbodiimide (DCC) and 4- The reaction is carried out in dichloromethane in the presence of dimethylaminopyridine (DMAP). After the reaction is stopped, the structural formula is Compound B (i.e. thiophene acetone derivatives, for R 1 , R 2 Different substituents, the chemical names in each embodiment will be different, see each embodiment for details);

[0034] Wherein, the m...

Embodiment 1

[0053] This embodiment discloses a benzodithiophene copolymer containing benzothiadiazole units with the following structure (R 1 =R 2 = H, R 3 = Octyloxy, R 4 = H, R 5 =R 6 = Octyloxy):

[0054] n=60;

[0055] The preparation steps of the above-mentioned benzodithiophene copolymer containing benzothiadiazole units are as follows:

[0056] One, the preparation of 1,3-two (2-thiophene) acetone

[0057]

[0058] First, with 70 mL treated dichloromethane (CH 2 Cl 2) Dissolve 7.6g (36.8mmol) of 1,3-dicyclohexylcarbodiimide (DCC) and 1.23g (10mmol) of 4-dimethylaminopyridine (DMAP) to obtain a mixed solution. Under nitrogen protection, the A solution of 5 g (35.2 mmol) of 2-thiopheneacetic acid in 70 mL of dichloromethane was added dropwise to the mixed solution and reacted overnight. After the reaction, the reaction solution was filtered, and recrystallized twice with n-hexane, and then separated and purified by column chromatography to obtain the structural formula...

Embodiment 2

[0077] This embodiment discloses a benzodithiophene copolymer containing benzothiadiazole units with the following structure (R 1 = Hexyl, R 2 = H, R 3 = methyl, R 4 = H, R 5 =R 6 = tetradecyloxy):

[0078] n=50;

[0079] The preparation steps of the above-mentioned benzodithiophene copolymer containing benzothiadiazole units are as follows:

[0080] 1. Preparation of 1,3-bis(3-hexyl-5-thiophene)acetone:

[0081]

[0082] First, with 70 mL treated dichloromethane (CH 2 Cl 2 ) Dissolve 7.6g (36.8mmol) of 1,3-dicyclohexylcarbodiimide (DCC) and 1.23g (10mmol) of 4-dimethylaminopyridine (DMAP) in the presence of mixed gas of argon and nitrogen , 60 mL of dichloromethane solution dissolved with 8.0 g (35.2 mmol) of 3-hexyl-5-thiopheneacetic acid was added dropwise to the above reaction solution, and reacted overnight. After the reaction, the reaction solution was filtered, recrystallized twice with n-hexane, and then separated and purified by column chromatography to...

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Abstract

The invention belongs to the field of an organic semiconductor material, and discloses a dibenzothiophene copolymer containing a diazosulfide unit as well as a preparation method and application of the dibenzothiophene copolymer. The copolymer has the following structure general formula, wherein in the formula, n is an integer of 10-60, R1 and R2 are identically or differently H and C1-C16 alkyls; R3 and R4 are identically or differently H, C1-C16 alkyls or C1-C16 alkoxys; R5 and R6 are identically or differently represented by H or C1-C16 alkyls, C1-C16 alkoxys or F. By adopting the dibenzothiophene copolymer containing the diazosulfide unit, a copolymer molecule of 'weak donor-strong acceptor' is formed by copolymerization of a thionaphthene monomer and other strong acceptor units (diazosulfide), so that the utilization rate of the material on the sunlight is improved.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to a benzodithiophene copolymer containing benzothiadiazole units, a preparation method and application thereof. Background technique [0002] Organic solar cells have attracted widespread attention as a potential renewable energy source because of their incomparable advantages over inorganic solar cells, such as low cost, simple manufacturing process, light weight, and large-area flexible preparation. The performance of organic solar cells has steadily improved over the past decade, with energy conversion efficiencies approaching 10%. Although the energy conversion efficiency of organic solar cells has been greatly improved, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells. Therefore, in order to realize the commercialization of organic solar cells, the development of new organic semiconductor materials ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕李满园黄佳乐黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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