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Copolymer containing cyclopentadithiophene and benzodi(benzoselenadiazole), and preparation method and application thereof

A technology containing cyclopentadiene dithiophene and cyclopentadiene dithiophene, which is applied in the field of solar cell materials, can solve the problems of low photoelectric conversion efficiency and the like, and achieves advantages such as film forming processing, high yield and good stability Effect

Inactive Publication Date: 2014-06-18
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

However, the photoelectric conversion efficiency of copolymer solar cells is much lower than that of silicon solar cells. If the photoelectric conversion efficiency of copolymer solar cells can be raised to a level close to commercial silicon solar cells, its market prospect will be very huge

Method used

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  • Copolymer containing cyclopentadithiophene and benzodi(benzoselenadiazole), and preparation method and application thereof
  • Copolymer containing cyclopentadithiophene and benzodi(benzoselenadiazole), and preparation method and application thereof
  • Copolymer containing cyclopentadithiophene and benzodi(benzoselenadiazole), and preparation method and application thereof

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Experimental program
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preparation example Construction

[0067] In addition, this embodiment also provides a preparation method of a copolymer containing cyclopentadiene dithiophene and benzobis(benzoselenodiazole) units, such as figure 1 shown, including the following steps:

[0068] Step S110, providing compound A and compound B. The structural formula of compound A is:

[0069]

[0070] The structural formula of compound B is:

[0071]

[0072] Among them, R 1 , R 2 , R 3 and R 4 for C 1 ~C 20 of alkyl.

[0073] Step S120, under a protective gas atmosphere, compound A and compound B are subjected to a Stille coupling reaction in the presence of a catalyst and an organic solvent at a molar ratio of 1:1.5 to 1.5:1, wherein the reaction temperature is 50 to 120 ℃, and the reaction time is 6 to 100 hours. After separation and purification, a copolymer containing cyclopentadiene dithiophene and benzobis(benzoselenadiazole) units with the following structural formula is obtained,

[0074]

[0075] Wherein, n is an in...

Embodiment 1

[0133] P1: Poly{4,4-dioctyl-cyclopentadieno[2,1-b;3,4-b']dithiophene-6,7-bis(3,7-dimethyl)octyl - benzo[2,1-e:3,4-e]bis(benzoselenodiazole)}, having the following structural formula:

[0134]

[0135] The preparation process of above-mentioned copolymer P1 is as follows:

[0136] Step 1, preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0137]

[0138] Add 0.15 mol of 2-amino-5-nitroaniline and 100 mL of thionyl chloride into the three-necked flask, and slowly add 2 mL of pyridine dropwise to the three-necked flask under stirring conditions, and then heat and reflux for 24 hours; heat the reaction solution After the excess thionyl chloride is evaporated at 80°C, the reaction product cooled to room temperature is poured into a large amount of water and stirred; filtered to obtain a solid substance, and the solid substance after washing with water is vacuum-dried to obtain the product 5-nitro -2,1,3 benzothiadiazole 21.7g, yield 80%.

[0139] Step 2, preparation ...

Embodiment 2

[0165] P2: Poly{4,4-dimethyl-cyclopentadieno[2,1-b;3,4-b']dithiophene-6,7-bis(3,7-dimethyl)octyl - benzo[2,1-e:3,4-e]bis(benzoselenodiazole)}, having the following structural formula:

[0166]

[0167] The preparation process of above-mentioned copolymer P2 is as follows:

[0168] Steps 1-7 are the same as Steps 1-7 of Example 1.

[0169] Step 8. Preparation of 4,4-dimethyl-2,6-bis(tributyltin)-cyclopentadieno[2,1-b;3,4-b']dithiophene

[0170]

[0171] Under the protection of nitrogen, add 0.01mol 4,4-dimethyl-2,6-dibromocyclopentadiene[2,1-b;3,4-b']dithiophene and 40ml tetrahydrofuran into the three-necked flask solvent to obtain a mixed solution; slowly inject 8.6mL of n-butyllithium (0.02mol) into the mixed solution with a syringe under the condition of -78°C, and continue to stir and react for 1.5 hours; Inject 5.6mL of tributyltin chloride (0.02mol) into the solution, stir for 1 hour, then warm up to room temperature and continue to stir for 6 hours; add 30ml of ...

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Abstract

The invention relates to a copolymer containing cyclopentadithiophene and benzodi(benzoselenadiazole), and the structural formula is shown in the specification. In the structural formula, n is an integer between 1 to 100, and R1, R2, R3 and R4 are C1-C20 alkyl. The copolymer has the characteristics of wide light absorption scope, high carrier mobility, good solubility, good film forming property and the like, and is applicable to copolymer solar cell devices, organic electroluminescent devices, organic field effect transistors, organic optical storage and organic laser and the like. Additionally, the invention also provides a preparation method for the copolymer containing cyclopentadithiophene and benzodi(benzoselenadiazole), and the preparation method is mild in conditions, easy to control and high in product yield.

Description

technical field [0001] The invention relates to the technical field of solar cell materials, in particular to a copolymer containing cyclopentadiene dithiophene and benzobis(benzoselenodiazole) units, its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Although the traditional silicon solar cell has high efficiency, its production process is complicated and the cost is high, which limits its further application. In order to reduce the production cost of solar cells and expand their application range, people have been looking for new solar cell materials. [0003] Copolymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, good flexibility, simple production process, and large-area flexible preparation. However, the photoelectric conversion ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D519/00H01L51/54H01L51/46
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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