Bi-thiophene silole-containing conjugated polymer and preparation method and application thereof

A technology of conjugated polymer and thiophene thiorole, which is applied in the field of organic compound synthesis, can solve the problems of low collection efficiency of carrier electrodes, ineffective use of red light region, low carrier mobility, etc., and achieve excellent electrical conductivity. Effects of chemical reduction properties, enhanced reduction potential, improved transport properties

Inactive Publication Date: 2011-10-05
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
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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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  • Bi-thiophene silole-containing conjugated polymer and preparation method and application thereof
  • Bi-thiophene silole-containing conjugated polymer and preparation method and application thereof
  • Bi-thiophene silole-containing conjugated polymer and preparation method and application thereof

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preparation example Construction

[0039] And, the embodiment of the present invention also provides the preparation method of the conjugated polymer containing dithiophene thiazoles, including the following chemical reaction formula:

[0040]

[0041] That is, the specific process steps included are:

[0042] (1) Compounds A, B, C, diketones and 3,4-diaminothiophene hydrogen chloride represented by the following structural formula are provided respectively,

[0043]

[0044] In the formula, any positive integer of x+y=1, 01 , R 2 from C 1 ~C 15 the alkyl group, R 3 , R 4 selected from -H, C 1 ~C 15 Alkyl, C 1 ~C 15 At least one of the alkoxy groups, alkyl or / and alkoxythiophene groups, alkyl fluorene groups, alkyl carbazole groups, and alkyl benzene ring groups;

[0045] (2) Under weak alkalinity and 0-78°C, the molar ratio of diketone compound and 3,4-diaminothiophene hydrogen chloride is 1:0.1-10 for dehydration reaction for 1-24h to obtain 2, 3-disubstituted-thieno[3,4-b]pyrazine;

[0046] ...

Embodiment 1

[0059] The following structural formula P 1 Polymer Synthesis:

[0060]

[0061] (1) 2, the preparation of 3-bisphenyl-thieno [3,4-b] pyrazine, its reaction is shown in the following formula:

[0062]

[0063] The specific process of preparation is: 3,4-diaminothiophene hydrochloride (1.0g, 5.34mmol) was added to the compound containing diphenyl ketone (1.12g, 5.34mmol) and triethylamine (10.68mmol) without To a solution of water and ethanol (100 mL), triethylamine (1.15 g, 11 mmol) was added and stirred at 78° C. for 1 hour under the condition of protecting from light. After the reaction, the solvent was removed by rotary evaporation of the reaction liquid, and a solid was obtained by column chromatography (dichloromethane as eluent). MS (EI) m / z: 288 (M + ).

[0064] (2) 5,7-dibromo 2, the preparation of 3-bisphenyl-thieno[3,4-b]pyrazine, its reaction is shown in the following formula:

[0065]

[0066] The specific process of preparation is: NBS (0.72g, 4mmol)...

Embodiment 2

[0071] The following structural formula P 2 Polymer Synthesis:

[0072]

[0073] (1) 2, the preparation of 3-bisphenyl-thieno [3,4-b] pyrazine, its reaction is shown in the following formula:

[0074]

[0075] The specific process of preparation is: 3,4-diaminothiophene hydrogen chloride (5.34mmol) is added to anhydrous ethyl acetate (100mL) solution of compound diphenylethanedione (0.534mmol) and sodium carbonate (26.7mmol) , then added triethylamine (1.15 g, 11 mmol) and stirred in an ice bath for 24 hours under light-shielding conditions, then the solvent was removed by rotary evaporation, and a solid was obtained by column chromatography (dichloromethane as eluent). MS (EI) m / z: 288 (M + ).

[0076] (2) 5,7-dibromo 2, the preparation of 3-bisphenyl-thieno[3,4-b]pyrazine, its reaction is shown in the following formula:

[0077]

[0078]The specific process of preparation is: NBS (0.72g, 4mmol) is added to tetrahydrofuran (THF) / N, N- Dimethylformamide (DMF) (v / ...

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Abstract

The invention discloses bi-thiophene silole-containing conjugated polymer and a preparation method and application thereof. The bi-thiophene silole-containing conjugated polymer has a molecular structure general formula (I) shown in the specifications, wherein in the general formula, x and y is equal to 1, x is more than 0 and less than or equal to 0.5, and n is any one positive integer which is more than 1 and less than or equal to 150; R1 and R2 is C1 to C15 alkyl groups; and R3 and R4 are at least one of -H, C1 to C15 alkyl groups, C1 to C15 alkoxy, an alkyl group or/and alkyl group-containing thiophene group, an alkyl group-containing fluorene group, an alkyl group-containing carbazole group and an alkyl group-containing benzene ring group. The bi-thiophene silole-containing conjugated polymer has a low energy gap, expands light-absorbing bandwidths, enhances reduction potentials, improves an electric charge transmission property and has higher chemical and structural paintability. The preparation method for the polymer is simple, high in yield, easy to operate and control and suitable for fields of solar batteries 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 polymer containing dithiophene thiazoles 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 commercial silicon solar...

Claims

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Application Information

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