Conjugated polymer material capable of being processed by green solvent and preparation method of conjugated polymer material

A technology of conjugated polymers and green solvents, applied in the field of conjugated polymer materials, can solve the problems of restricting commercial green production, and achieve the effects of wide absorption spectrum, good thermal stability, and obvious color change range

Pending Publication Date: 2022-01-28
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the same problem exists in the field of electrochromism. Although conjugated polymers have the advantages of high contrast, high coloring efficiency, and high cycle stability, the fused ring structure has a greater solubility in terms of solubility. challenges, and also limits its commercial green production

Method used

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  • Conjugated polymer material capable of being processed by green solvent and preparation method of conjugated polymer material
  • Conjugated polymer material capable of being processed by green solvent and preparation method of conjugated polymer material
  • Conjugated polymer material capable of being processed by green solvent and preparation method of conjugated polymer material

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preparation example Construction

[0084] The preparation method of the above-mentioned green solvent-processable conjugated polymer material comprises the following steps:

[0085] Under the interaction between the catalyst and the ligand, the structural monomers of formula (II-1), formula (II-2), formula (II-3) and formula (III) are subjected to Stille coupling reaction to obtain formula (I ) Conjugated polymers containing oligoethylene glycol side chain structure with structural repeating units, the reaction temperature is 110°C-250°C, and the reaction time is 10-48 hours;

[0086]

[0087]

[0088]

[0089] The structural formula of Q is as follows:

[0090]

[0091] In the formula, m is an integer of 2-10; Z is Cl, Br or I; X is S or Se; E is F or Cl.

[0092] The molar ratio of the structural monomers of formula (II-1), formula (II-2), formula (II-3) and formula (III) is 1:(0.8-1.5), preferably, the molar ratio is 1: 1.

[0093] The catalyst is a palladium catalyst, specifically one or more...

Embodiment 1

[0104] Synthesis of monomer

[0105] Synthesis of M1

[0106] Under the protection of argon, the monomer 4,7-dibromo-5,6-difluoro-2,1,3-benzothiadiazole (1mmol, 0.33g) and tris(dibenzylideneacetone Dipalladium)-chloroform adduct (0.08mmol, 83mg), tri(o-methylphenyl)phosphine (0.64mmol, 195mg), 15ml of anhydrous toluene were added to the reaction flask, followed by addition of tin monomer (2.4mmol , 1.35g), the temperature was raised to 110°C, and after 24 hours of reaction, the antipyretic was stopped. After removing the organic solvent by rotary evaporator. The crude product was purified by silica gel column chromatography using methanol / ethyl acetate (1:100) to obtain 0.2 g of orange-yellow liquid, yield 27.8%

[0107] Synthesis of M2

[0108]Add 8ml of anhydrous tetrahydrofuran into the reaction bottle, and then add NBS (2.4mmol, 0.43g) to disperse NBS in tetrahydrofuran, then add monomer M1 into the reaction system, and react at room temperature for 24 hours. After th...

Embodiment 2

[0110] Polymer Synthesis

[0111] 1. Synthesis of PDTBF-ThSe

[0112] Under the condition of argon protection, monomer 2,5-bistrimethyltin-selenophene (0.2mmol, 91.3mg), M4 (02mmol, 174.9mg), catalyst tris(dibenzylideneacetone dipalladium)- Chloroform adduct (6mmol, 6.2mg), ligand tri(o-methylphenyl)phosphine (0.048mmol, 14.6mg) were added in the reaction flask, then injected 3ml of anhydrous toluene into the reaction system, and the temperature was raised to 110°C, react for 48 hours. After the reaction, the polymer was sequentially extracted in petroleum ether, methanol, ethanol, ethyl acetate and chloroform to finally obtain a reddish-brown polymer with metallic luster.

[0113] 2. Synthesis of PDTBF-Th

[0114] Under the condition of argon protection, monomer 2,5-bistrimethyltin-based thiophene (0.2mmol, 82.0mg), M2 (0.2mmol, 174.9mg), catalyst tris(dibenzylideneacetone dipalladium)- Chloroform adduct (6mmol, 6.2mg), ligand tri(o-methylphenyl)phosphine (0.048mmol, 14.6...

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Abstract

The invention belongs to the field of organic photoelectric materials. In recent years, as wide application of donor (D)-acceptor (A) type conjugated polymers gradually attracts attention of people, in order to solve the problem that conjugated polymer materials capable of being processed by green solvents are deficient, the dissolving property of the materials in polar solvents is regulated and controlled through side chain modification, and necessary conditions are provided for green industrial production of solar cell devices and electrochromic devices in the future. In the field of solar cells, the material can be matched with numerous acceptor materials, and single-layer or laminated devices can be prepared through green solvent processing; and the material has high contrast in the field of electrochromism, can be prepared into an electrochromic device of a hydrogel electrolyte, can be compatible with a water electrolyte to prepare an environment-friendly electrochromic device, and reduces the influence of an organic electrolyte on the environment. The material has dual functions of photovoltaic and electrochromism, and can be prepared into a device integrating power generation, power storage and intelligent window in the future.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a green solvent-processable conjugated polymer material and a preparation method thereof. Background technique [0002] The donor (D)-acceptor (A) conjugated polymer has unique optical and electrochemical properties, and has potential applications in the fields of solar cells and electrochromic materials. In recent years, although polymer solar cells (PSCs) have made a major breakthrough in photoelectric conversion efficiency, with a photoelectric conversion efficiency of over 19%, toxic and harmful solvents such as chloroform and chlorobenzene are commonly used in the processing of polymer solar cells, which will cause damage to humans and the environment. [0003] Based on this, the development of green solvent-processed polymer solar cells is an important issue that needs to be solved urgently to realize commercial green production in the f...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/1424C08G2261/18C08G2261/228C08G2261/314C08G2261/334C08G2261/414C08G2261/54C08G2261/592H10K30/20Y02E10/549
Inventor 陈峥齐诗英李诗意贾松瑞邢真王琦琳
Owner JILIN UNIV
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