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Random copolymer with difluorobenzothiadiazole and quaterthiophene as main chain as well as preparation method and application of copolymer

A technology of difluorobenzothiadiazole and benzothiadiazole, which is applied in the field of random copolymers and its preparation and application, and can solve problems such as film production that have not been met yet.

Active Publication Date: 2018-03-27
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the alternating copolymers of difluorobenzothiadiazole and bitetrathiophene as the main chain, long side chains are usually required to obtain solution processability, so as to make films that can meet the performance requirements of optoelectronic devices; without any side chains or Adopt the corresponding polymer of this very short side chain of 2-ethylhexyl to have no report that can meet the film making

Method used

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  • Random copolymer with difluorobenzothiadiazole and quaterthiophene as main chain as well as preparation method and application of copolymer
  • Random copolymer with difluorobenzothiadiazole and quaterthiophene as main chain as well as preparation method and application of copolymer
  • Random copolymer with difluorobenzothiadiazole and quaterthiophene as main chain as well as preparation method and application of copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of 5,6 difluoro-4,7-dibromo-2,1,3-benzothiadiazole, the reaction formula is as follows:

[0023]

[0024] Add 5,6 difluoro-2,1,3-benzothiadiazole (3.44g, 20mmol) into a 250ml flask, add 100ml of concentrated sulfuric acid, after fully dissolving, add DBDMH (dibromohydantoin) in three batches ) (6.86g, 24mmol), stirred at 70°C for 4 hours. The reactant was poured into ice water, and the crude product was obtained by suction filtration, which was recrystallized with ethanol after passing through the column, and a white solid was obtained after suction filtration. through 13 CNMR analysis test showed that it was the target product 5,6-difluoro-4,7-dibromo-2,1,3-benzothiadiazole.

[0025] 13 C NMR (300MHz, CDCl3) δ (ppm) 153.67, 153.39, 150.20, 149.92, 148.84, 99.51, 99.39, 99.20.

Embodiment 2

[0027] The preparation of 4,7-bis[4-(2-decyltetradecyl)thiophen-2-yl]-5,6-difluoro-2,1,3-benzothiadiazole has the following reaction formula:

[0028]

[0029] Add 5,6 difluoro-4,7-dibromo-2,1,3-benzothiadiazole (330mg, 1.00mmol), 2-(tributyltin)-4-(2 -decyltetradecyl)thiophene (2.12g, 3.00mmol), nitrogen gas was passed for 30 minutes, then 268 mg of bis(triphenylphosphine)palladium dichloride was added, 15 ml of anhydrous toluene was added under nitrogen protection, and heated The reaction was refluxed for two days. Cool to room temperature after the reaction, pour into 100 ml of water, extract with dichloromethane and dry the organic phase with anhydrous magnesium sulfate, remove the solvent after separation, and separate with a silica gel column to obtain a yellow floc. through 1 HNMR, 13 CNMR analysis showed that the target product was 4,7-bis[4-(2-decyltetradecyl)thiophen-2-yl]-5,6-difluoro-2,1,3-benzothiadiazole .

[0030] 1 H NMR (300MHz, CDCl3) δ (ppm) 8.09 (d...

Embodiment 3

[0033] Preparation of 4,7-bis[5-bromo-4-(2-decyltetradecyl)thiophen-2-yl]-5,6-difluoro-2,1,3-benzothiadiazole, The reaction formula is as follows:

[0034]

[0035] Add 4,7-bis[4-(2-decyltetradecyl)thiophen-2-yl]-5,6-difluoro-2,1,3-benzothiadi Azole (808mg, 0.8mmol) and 15ml of tetrahydrofuran were added with bromosuccinimide (NBS) (315mg, 1.76mmol) under full stirring, and reacted in the dark at room temperature for 24 hours. After the reaction, add the reaction solution into water, extract with dichloromethane and wash the organic phase with water, dry the organic phase with anhydrous sodium sulfate, separate, remove the solvent and separate with a silica gel column to obtain an orange-red solid. through 1 HNMR, 13 CNMR, and elemental analysis tests showed that it was the target product 4,7-bis[4-(2-decyltetradecyl)thiophen-2-yl]-5,6-difluoro-2,1,3-benzo Thiadiazoles.

[0036] 1H NMR (300MHz, CDCl3) δ (ppm) 7.89 (s, 2H), 2.56 (d, J = 7.0Hz, 4H), 1.73 (s, 2H), 1.27 (...

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Abstract

The invention discloses a random copolymer with difluorobenzothiadiazole and quaterthiophene as a main chain as well as a preparation method and application of the copolymer. According to the invention, random copolymerization is carried out by changing a way that two adjacent thiophene substituent groups of difluorobenzothiadiazole are combined according to length, so that a corresponding randomcopolymer is obtained. The prepared random copolymer with the difluorobenzothiadiazole and quaterthiophene as the main chain has good light absorbing property and solution processability, a light absorbing active layer oriented to a polymer solar cell can be produced, and the polymer solar cell can have high energy conversion efficiency. The prepared random copolymer with the difluorobenzothiadiazole and quaterthiophene as the main chain can enable the polymer solar cell to have good thermal stability, and an alternate copolymer adopting a long side chain cannot enable the polymer solar cell to obtain the same thermal stability.

Description

technical field [0001] The invention relates to a new type of polymer used in the field of polymer solar cells, more specifically to a random copolymer with difluorobenzothiadiazole and bitetrathiophene as the main chain and its preparation and application. Background technique [0002] Since Japanese scientist Hideki Shirakawa discovered that polyacetylene conducts electricity in 1977, this conductive polymer, known as the "fourth generation polymer" material, has attracted many scientists for its outstanding photoelectric properties. Compared with inorganic materials with the same or similar uses, conductive polymers have the advantages of low density, easy processing, and wide range of synthesis options. Due to the conjugation characteristics of this kind of material structure, it is easy to obtain fluorescence, absorb sunlight, and transport carriers, so it can or may be applied in many electronic or optoelectronic devices, such as polymer Light-emitting diodes, polymer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46H01L51/48
CPCC08G61/123C08G61/126C08G2261/3223C08G2261/146C08G2261/3246C08G2261/1412C08G2261/122C08G2261/91H10K85/151H10K85/113H10K30/15Y02E10/549
Inventor 陈军武钟安星卿乐驰
Owner SOUTH CHINA UNIV OF TECH
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