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Preparation method of self-doped thiophene polymer

A polymer and self-doping technology, which is applied in the field of preparation of self-doping thiophene block copolymers, can solve the problems of poor compatibility and dispersion, achieve good molding and processing performance, and be beneficial to material properties and reaction The effect of mild conditions

Active Publication Date: 2015-07-15
HEFEI UNIV OF TECH
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  • Abstract
  • Description
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Problems solved by technology

[0005] In order to solve the problem of poor compatibility and dispersion between dopants and conjugated polymers, avoid the dedoping phenomenon of conjugated polymers caused by heat generation in device applications, improve the stability of device performance, and achieve high conjugated polymers Large-area molding and soluble processing of molecules, the invention provides a method for preparing self-doping conductive polymer materials

Method used

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  • Preparation method of self-doped thiophene polymer
  • Preparation method of self-doped thiophene polymer
  • Preparation method of self-doped thiophene polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]Embodiment 1: the synthesis of 3-hexylthiophene-b-sodium styrene sulfonate block copolymer

[0026] Step 1, preparation of ethylene-terminated poly-3-hexylthiophene:

[0027] With 100 mL of anhydrous tetrahydrofuran (relative density 0.8892) as the reaction solvent, add 3.26 g of 2,5-dibromo-3-hexylthiophene and 5 mL of tetrahydrofuran with butylmagnesium chloride at a concentration of 2 mol / L (M) (density 0.93 g / mL) Solution, the molar ratio of 2,5-dibromo-3-hexylthiophene and butylmagnesium chloride consumption is 1:1, the mass sum of 2,5-dibromo-3-hexylthiophene and butylmagnesium chloride and anhydrous tetrahydrofuran The mass ratio is 1:11; under the condition of nitrogen protection, the temperature is 0°C, and the reaction is stirred for 2 hours to obtain a reaction system; 0.065g of 1,3-bisdiphenylphosphinopropane nickel dichloride (Ni (dppp)Cl 2 ) catalyst for coupling reaction, Ni(dppp)Cl 2 The molar ratio of the dosage to the dosage of 2,5-dibromo-3-hexylthi...

Embodiment 2

[0035] Example 2: Synthesis of 3,4-ethylenedioxythiophene-b-sodium p-styrenesulfonate block copolymer

[0036] Step 1, the preparation of ethylene-terminated poly-3,4-ethylenedioxythiophene:

[0037] With 100 mL of anhydrous tetrahydrofuran (relative density 0.8892) as the reaction solvent, add 3 g of 2,5-dibromo-3,4-ethylenedioxythiophene and 5 mL of butane with a concentration of 2 mol / L (M) (density 0.93 g / mL) The tetrahydrofuran solution of butylmagnesium chloride, the molar ratio of the amount of 2,5-dibromo-3,4-ethylenedioxythiophene and the amount of butylmagnesium chloride is 1:1, 2,5-dibromo-3,4-vinyldioxythiophene The mass ratio of the sum of the mass of oxythiophene and butylmagnesium chloride to anhydrous tetrahydrofuran is 1:12; under the condition of nitrogen protection, the temperature is 0°C, and the reaction is stirred for 2 hours to obtain a reaction system; then add 0.108g of 1,3-bisdiphenylphosphinopropane nickel dichloride (Ni(dppp)Cl 2 ) catalyst for co...

Embodiment 3

[0044] Embodiment 3: Synthesis of 3-methylthiophene-b-ethylene sulfonate sodium block copolymer

[0045] Step 1, preparation of ethylene-terminated poly-3-methylthiophene

[0046] Prepared according to step 1 in Example 1, the dibromomonomer used is 2,5-dibromo-3-methylthiophene, and the alkylmagnesium halide Grignard reagent used has a concentration of 1mol / L (M) (density 0.941g / mL) tetrahydrofuran solution of isobutylmagnesium bromide;

[0047] Step 2, preparation of self-doping type 3-methylthiophene-b-sodium ethylene sulfonate block copolymer

[0048] It was prepared according to step 2 in Example 1, and the doping monomer used was sodium vinyl sulfonate.

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Abstract

The invention relates to a preparation method of a self-doped thiophene polymer. The structural general formula of the self-doped thiophene polymer is AmBn, wherein the section A structure can be poly(3-alkylthiophene), poly(3-alkoxythiophene) or poly(3,4-vinyldioxythiophene); the alkyl of the poly(3-alkylthiophene) can be methyl, ethyl, hexyl, octyl, decyl or dodecyl; the alkoxy of the poly(3-alkoxythiophene) can be methoxy, ethoxy, hexyloxy, octyloxy, decyloxy and dodecyloxy; m is 1-100; the section B is poly(sodium vinylsulfonate) or poly(sodium-p-styrenesulfonate); and n is 1-100. The preparation method comprises the following steps: performing halogen-metal exchange reaction to prepare a vinyl-terminated thiophene polymer, and then performing radical copolymerization with a sodium vinylsulfonate or sodium p-styrenesulfonate monomer to obtain the self-doped thiophene block copolymer. The preparation method overcomes the dedoping phenomenon caused by heat generation in application of a conjugated polymer material in devices.

Description

technical field [0001] The invention belongs to the technical field of conductive polymer preparation, and in particular relates to a preparation method of a self-doping thiophene block copolymer. Background technique [0002] Polythiophene and its derivatives have the advantages of good environmental thermal stability, controllable molecular chain structure, and easy charge transfer between molecular chains. They are one of the most promising matrix materials in conductive polymers. Common varieties such as polyalkylene thiophene and poly 3,4-ethylenedioxythiophene (PEDOT) have achieved good application results in the fields of solar cells, light-emitting diodes, field effect transistors, sensors, and energy storage. . Conjugated polymers have wide band gaps and poor conductivity due to lattice defects, van der Waals forces, and molecular plane distortions caused by steric hindrance effects, so undoped eigenstate conjugated polymers have fewer carriers , very low conducti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F290/06C08F228/02C08F212/14C08F2/06C08G61/12
Inventor 汪瑾郭晨忱罗小霞吴宗超
Owner HEFEI UNIV OF TECH
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