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Dithiophene-containing thiophene-thiophene-quinoxaline conjugated polymer and its preparation method and application

A technology of conjugated polymer and thiophene thiorole, which is applied in the field of organic compound synthesis, can solve the problems of underutilized red light region, low collection efficiency of carrier electrodes, low carrier mobility, etc., and achieve excellent electrical properties. Effects of chemical reduction properties, good thermal and environmental stability, and high electron transport properties

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

At present, the research on polymer solar cells mainly focuses on the blending system of donor and acceptor, using PTB7 and PC 71 The energy conversion efficiency of the BM blend system has reached 7.4%, but it is still much lower than the conversion efficiency of inorganic solar cells. The main constraints that limit the performance improvement are: the relatively low carrier mobility of organic semiconductor devices, the device’s The spectral response does not match the solar radiation spectrum, the red light region with high photon flux is not effectively utilized, and the electrode collection efficiency of carriers is low, etc.

Method used

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  • Dithiophene-containing thiophene-thiophene-quinoxaline conjugated polymer and its preparation method and application
  • Dithiophene-containing thiophene-thiophene-quinoxaline conjugated polymer and its preparation method and application
  • Dithiophene-containing thiophene-thiophene-quinoxaline conjugated polymer and its preparation method and application

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preparation example Construction

[0042] This embodiment also provides a method for preparing the above-mentioned conjugated polymer containing dithiophene thiazole-thiophene-quinoxaline, including the following steps:

[0043] 1) Provide compounds A, B, C, and D represented by the following structural formula respectively,

[0044]

[0045] Among them, R 1 from C 1 ~C 20 the alkyl group; R 2 , R 3 selected from -H, C 1 ~C 20 Alkyl, C 1 ~C 20 Alkoxy groups, alkyl or alkoxy benzene ring groups, alkyl fluorene groups or alkyl carbazole groups; R 4 , R 5 selected from -H, C 1 ~C 20 Alkyl or C 1 ~C 20 alkoxy;

[0046] 2) In an oxygen-free environment and in the presence of a catalyst and an organic solvent, select compounds A, B, C, and D to carry out a Stille coupling reaction to obtain a dithiophene-containing thiazole-thiophene- Quinoxaline conjugated polymers. The Stille coupled chemical reaction formula of step 2) can be expressed as follows:

[0047]

[0048] In the general structural ...

Embodiment 1

[0057] Dithiophene [3,2-b: 2', 3'-d] silole-thiophene-2, the preparation of 3 two (phenyl substituted) quinoxaline conjugated polymers, its structural formula is as follows I 1 as shown,

[0058]

[0059] Its preparation steps are as follows:

[0060] 1) The preparation of compound 2,5-dibromo-4,5 dioctylthiophene, its chemical reaction formula is as follows:

[0061]

[0062] The specific process of preparation is: NBS (2.9g, 16.3mmol) was added to the DMF (50mL) solution containing 3,4-dioctylthiophene (2.1g, 6.8mmol), stirred at room temperature for 12 hours, and the reaction solution was poured into into saturated brine, followed by chloroform extraction, saturated brine washing, rotary evaporation to remove the solvent to obtain the crude product, the crude product was obtained by column chromatography (petroleum ether as eluent) to obtain an oily product, the yield was 76%, and the MS (EI) m / z of the product: 466 (M + ).

[0063] 2) The preparation of compound ...

Embodiment 2

[0073] Dithiophene [3,2-b: 2', 3'-d] silole-thiophene-2, the preparation of 3 two (phenyl substituted) quinoxaline conjugated polymers, its structural formula is as follows I 2 as shown,

[0074]

[0075] Its preparation steps are as follows:

[0076] 1) According to the same preparation method and similar reaction conditions of step 1) in Example 1, the compound 2,5-dibromo-3,4-dioctyloxythiophene with the following structural formula was prepared,

[0077]

[0078] 2) According to the same preparation method and similar reaction conditions in step 2) in Example 1, 5,8-dibromo-2-(4-n-butylphenyl) 3-(4-eicosane) with the following structural formula was prepared Oxyphenyl)quinoxaline,

[0079]

[0080] 3) According to the same preparation method and similar reaction conditions as step 3) in Example 1, 4,4'-di-n-butyl-2,6-bistrimethyltin-dithiophene [3,2 -b:2',3'-d] silole,

[0081]

[0082] 4) Cyclopentadiene (2,1-b:3,4-b') dithiophene-thiophene-2,3 bis(phenyl ...

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Abstract

The invention discloses a conjugated polymer containing dithiophene thiazole-thiophene-quinoxaline and its preparation method and application. The general formula of its molecular structure is (I), where x+y+z=2, and x≥1, 0<z<1, 0<y<1; n is an integer, and 1<n≤150; R1 is selected from C1~C20 alkyl; R2, R3 are selected from -H, C1~C20 alkane group, C1~C20 alkoxy group, alkyl group or alkoxy benzene ring group, alkyl fluorene group or alkyl carbazole group; R4, R5 are selected from -H, C1~C20 alkane group or C1-C20 alkoxy group. The copolymer has high crystallization properties, good charge transport properties, thermal stability and environmental stability, and excellent electrochemical reduction properties, which can weaken bimolecular recombination, increase carrier mobility, and broaden the spectrum. Response, at the same time, its preparation process is simple, the yield is high, and it is easy to operate and control.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a conjugated polymer containing dithiophene thiazole-thiophene-quinoxaline and 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. 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 that of com...

Claims

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Application Information

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