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Ethylenedioxothiophene-and-naphthalene-tetracarboxylic-acid-bisimide-structural-unit-based low band gap polymers, and preparation method and application method thereof

A technology of tetracarboxylic diimide and ethylenedioxythiophene, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., and can solve the problems of low polymer yield and low polymer molecular weight

Inactive Publication Date: 2012-06-13
SHANGHAI ENTRY EXIT INSPECTION & QUARANTINE BUREAU OF P R C
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the defect of this technology is that the productive rate of forming polymer is low (60.5%), and the molecular weight of the obtained polymer is low

Method used

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  • Ethylenedioxothiophene-and-naphthalene-tetracarboxylic-acid-bisimide-structural-unit-based low band gap polymers, and preparation method and application method thereof
  • Ethylenedioxothiophene-and-naphthalene-tetracarboxylic-acid-bisimide-structural-unit-based low band gap polymers, and preparation method and application method thereof
  • Ethylenedioxothiophene-and-naphthalene-tetracarboxylic-acid-bisimide-structural-unit-based low band gap polymers, and preparation method and application method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 prepares alternating copolymer P1

[0028] 1) Preparation of alternating copolymer P1

[0029] Monomer N,N'-bis-(2',6'-diisopropylphenyl)-2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid diimide (1) and Monomer 2,5-bis(tributyltin)-3,4-ethylenedioxythiophene (2) is polymerized by Stille coupling.

[0030]

[0031] Specifically: first place the monomers (1) and (2) and the catalyst tris(dibenzylideneacetone) dipalladium (0), triphenylarsenic and cuprous iodide in a long-necked sealed reaction with a branch In the bottle, use a double-row tube to evacuate, nitrogen, and then evacuate, repeat this three times to completely remove the oxygen in the system, then add the newly distilled tetrahydrofuran solvent with a syringe, and then blow nitrogen with positive pressure to remove oxygen for 20 minutes, then completely seal the reaction bottle with a sealing tape, heat it to 80°C with an oil bath for reaction, and keep it for 72 hours, and then undergo po...

Embodiment 2

[0047] Embodiment 2 prepares random copolymer P2

[0048] 1) Preparation of random copolymer P2:

[0049] By adding 2,5-dibromo-3,4-ethylenedioxythiophene (3) monomer, and 2,5-di(tributyltin)-3,4-ethylenedioxythiophene (2) and N, N'-bis-(2',6'-diisopropylphenyl)-2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid diimide (1) monomer, participating together Random copolymer P2 was prepared by Stille coupling polymerization.

[0050]

[0051] The purpose of the design of this embodiment is to increase the component of the electron donor unit 3,4-ethylenedioxythiophene in the copolymer product, so as to achieve the purpose of further red-shifting its absorption spectrum and having a relatively broader absorption. The ultraviolet spectrum shows that the expected effect has been obtained. Wherein, 3,4-ethylenedioxythiophene was brominated with N-bromosuccinimide in a mixed solution of chloroform and glacial acetic acid, and purified by column chromatography and recrystallizat...

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Abstract

The invention discloses ethylenedioxothiophene-and-naphthalene-tetracarboxylic-acid-bisimide-structural-unit-based low band gap polymers, and a preparation method and an application method thereof, and belongs to the technical field of chemical photoelectric materials. The preparation method comprises the following steps of: performing Stille coupling polymerization reaction on a monomer, namely 2,5-bis(tributyltin)-3,4-ethylenedioxothiophene, and a monomer, namely N,N'-bis-(2',6'-diisopropylphenyl)-2,6-dibromonaphthyl-1,4,5,8-tetracarboxylic acid bisimide to obtain a target alternate copolymer P1 with moderate molecular weight; and further copolymerizing the alternate copolymer and a monomer, namely 2,5-dibromo-3,4-ethylenedioxothiophene by a Stille coupling polymerization method to obtain a random copolymer P2. The two polymers prepared by the method have lower optical band gaps and broader spectral absorption, and have a great application prospect in solar battery materials and other photoelectric devices.

Description

technical field [0001] The invention relates to the technical field of chemical photoelectric materials, in particular to a low-energy bandgap polymer based on structural units of ethylenedioxythiophene and naphthalene tetracarboxylic acid diimide and its preparation and application methods. Background technique [0002] Polymer solar cells have the advantages of wide material sources, light weight, simple preparation process, large-area film formation, and flexibility, and have become a hot spot that people have paid attention to in recent years. Low-bandgap conjugated polymers with delocalized π-electron systems are widely used in the design and synthesis of high-performance polymer solar cell materials due to their better matching with the solar spectrum. The maximum photon flow of sunlight is around 700nm. In order to match the absorption spectrum of the conjugated polymer with the solar spectrum, the absorption peak position of the polymer should be around 700nm, which ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 魏宇峰张继东吴晓红费旭东赵波王文青邱丰沈波
Owner SHANGHAI ENTRY EXIT INSPECTION & QUARANTINE BUREAU OF P R C
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