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Cyclopenta(2,1-b:3,4-b')dithiophene-thieno[3,4-b]pyrazine conjugated polymer and preparation method and use thereof

A technology of conjugated polymers and cyclopentadiene, which is applied in the fields of final product manufacturing, sustainable manufacturing/processing, semiconductor/solid-state device manufacturing, etc., can solve the problems of low carrier mobility, low conversion efficiency, and ineffective Taking advantage of the collection efficiency of the carrier electrode to achieve excellent electrochemical reduction properties, lower energy gap, and easy transfer

Inactive Publication Date: 2011-07-20
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research of polymer solar cells is mainly focused on the blending system of donor and acceptor, and the energy conversion efficiency of PCPDTBT and PCBM blending system has reached 6.5% (Jin Young Kim, et al.Science 2007, 317, 222) , but the conversion efficiency is still much lower than that of inorganic solar cells. The main constraints that limit the performance improvement are: the relatively low carrier mobility of organic semiconductor devices, the spectral response of the device does not match the solar radiation spectrum, and the high photon flux. The amount of red light is not effectively utilized and the electrode collection efficiency of carriers is low.

Method used

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  • Cyclopenta(2,1-b:3,4-b')dithiophene-thieno[3,4-b]pyrazine conjugated polymer and preparation method and use thereof
  • Cyclopenta(2,1-b:3,4-b')dithiophene-thieno[3,4-b]pyrazine conjugated polymer and preparation method and use thereof
  • Cyclopenta(2,1-b:3,4-b')dithiophene-thieno[3,4-b]pyrazine conjugated polymer and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of 2,3-bisphenyl-thieno[3,4-b]pyrazine:

[0051]

[0052] Under nitrogen protection, 3,4-diaminothiophene·hydrogen chloride (1.0 g, 5.34 mmol) was added to a solution of compound diphenylethanedione (1.12 g, 5.34 mmol) in absolute ethanol (100 mL). Then, under light-shielded conditions, triethylamine (1.15 g, 11 mmol) was added, stirred and reacted at 45° C. for 18 hours. The solvent was removed by rotary evaporation, and the solid was obtained by column chromatography (dichloromethane as eluent) with a yield of 69%. MS (EI) m / z: 288.4 (M+).

Embodiment 2

[0054] Preparation of 5,7-dibromo2,3-diphenyl-thieno[3,4-b]pyrazine:

[0055]

[0056] NBS (0.72g, 4mmol) was added to chloroform / acetic acid (v / v=1 / 1) containing compound 2,3-bisphenyl-thieno[3,4-b]pyrazine (0.49g, 1.7mmol) , 10 mL) solution, heated at 65°C and stirred for 6 hours. The reaction liquid was extracted with chloroform in a saturated sodium carbonate solution, washed with water, and dried over anhydrous sodium sulfate. The solvent was spun off, and a solid was obtained by column chromatography with a yield of 55%. MS (EI) m / z: 446 (M+).

Embodiment 3

[0058] Preparation of 5,7-dibromo 2-(3-(nitrohexylcarbazol)yl)-3-phenyl-thieno[3,4-b]pyrazine:

[0059]

[0060] NBS (0.43g, 2.4mmol) was added to the compound containing In a solution of N,N-dimethylformamide (DMF), the temperature was kept at 3°C ​​and the reaction was stirred for 45 hours. The reaction liquid was extracted with chloroform in a saturated sodium carbonate solution, washed with water, and dried over anhydrous sodium sulfate. The solvent was spun off, and a solid was obtained by column chromatography with a yield of 81%. MS (MALDI) m / z: 619 (M+).

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Abstract

The invention discloses a cyclopenta(2,1-b:3,4-b')dithiophene-thieno[3,4-b]pyrazine conjugated polymer of a general formula (I) and a preparation method and use thereof. The preparation method comprises: reacting a diketone compound with 3,4-diaminothiophene.hydrogen chloride; subjecting the product of the reaction to bromination with N-bromosuccinimide (NBS) to obtain a target monomer; and underan oxygen-free condition, subjecting the 4,4-dialkyl-2,6-bis(trimethylstannyl)-cyclopenta(2,1-b:3,4-b')dithiophene, 4,4-dialkyl-2,6-dibromo-cyclopenta(2,1-b:3,4-b')dithiophene and the target monomer to polymerization to obtain the product disclosed by the invention. The preparation method disclosed by the invention is simple, makes operation and control easy, and is suitable for industrial production. Because a long-chain alkyl is introduced into the molecule of the polymer, the solubility and processability of the polymer are improved. The polymer can be widely used in fields of polymer solar cells and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a conjugated cyclopentadiene (2,1-b:3,4-b') dithiophene-thieno[3,4-b]pyrazine Polymers and their preparation and applications. 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. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energy conversion efficiency can be improved to be close to th...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46H01L51/54H01L51/30H01L51/00
CPCY02E10/50Y02E10/549Y02P70/50
Inventor 周明杰黄杰许二建
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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