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A kind of fluorine-containing triphenylamine copolymer and preparation method thereof

A technology of triphenylamine and copolymer, which is applied in the field of fluorine-containing triphenylamine copolymer and its preparation, can solve the problem that the improvement of polymer hydrophobicity is not effective, and achieve the effect of excellent hydrophobicity and excellent photoelectric performance

Active Publication Date: 2021-06-22
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the triphenylamine copolymers reported by patent CN103741259B and patent CN105070830B, the triphenylamine structural unit only has an oxygen-containing electron-donating group, and the conjugated unit copolymerized with it does not contain fluorine; Guntae Kim et al. reported fluorine-containing polytriphenylamine , systematically studied the basic properties of the prepared polytriphenylamine (GuntaeKim, Fevzihan Basarir, Tae-Ho Yoon.Synthetic Metals, 161(2011)2092–2096), but the synthesized triphenylamine copolymer only contains trifluoromethyl groups, And it is directly connected to the main chain of the polymer, which has little effect on improving the hydrophobicity of the polymer.

Method used

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  • A kind of fluorine-containing triphenylamine copolymer and preparation method thereof
  • A kind of fluorine-containing triphenylamine copolymer and preparation method thereof
  • A kind of fluorine-containing triphenylamine copolymer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Preparation of fluorine-containing fluorene monomer, 2,7-dibromo-9,9-bis(hexafluorobutyl propionate)fluorene:

[0039] After a magnetic stirrer was placed in a 100mL three-necked flask equipped with a thermometer, 3.3g (10.2mmol) 2,7-dibromofluorene, 0.25g (0.78mmol) tetrabutylammonium bromide and 25mL toluene were added successively, and vacuumized Nitrogen was blown to maintain the nitrogen atmosphere, and then 5 mL of 50% potassium hydroxide aqueous solution was slowly added dropwise with a syringe. After magnetic stirring for about 30 minutes, use an ice-water bath, and after the temperature of the reaction system is constant, add 9.676 g (41 mmol) of hexafluorobutyl acrylate dropwise with a syringe. After the hexafluorobutyl acrylate was added dropwise, the stirring was continued for about 1 hour, and the temperature was raised to 25° C. for 6 hours. After the reaction, the reaction solution was poured into a separatory funnel, diluted with an appropriate amount o...

Embodiment 2

[0041] Preparation of fluorine-containing fluorene monomer, 2,7-dibromo-9,9-bis(dodecafluoroheptyl propionate)fluorene:

[0042] After placing a magnetic stirrer in a 100mL three-neck flask equipped with a thermometer, add 3.3g (10.2mmol) 2,7-dibromofluorene, 0.16g (0.78mmol) tetraethylammonium bromide and 25mL dichloroethane , evacuated and ventilated with nitrogen to maintain the nitrogen atmosphere, and then slowly added 5 mL of 50% sodium hydroxide aqueous solution dropwise with a syringe. After magnetic stirring for about 30 minutes, use an ice-water bath, and after the temperature of the reaction system is constant, add 15.832 g (41 mmol) of dodecafluoroheptyl acrylate dropwise with a syringe. After the dodecafluoroheptyl acrylate was added dropwise, stirring was continued for about 1 h, and the temperature was raised to 30° C. for 8 h. After the reaction, pour the reaction solution into a separatory funnel, add an appropriate amount of dichloroethane to dilute, wash an...

Embodiment 3

[0044] Preparation of fluorine-containing fluorene monomer, 2,7-dibromo-9,9-di(tridecafluorooctyl propionate) fluorene:

[0045] After placing a magnetic stirrer in a 100mL three-neck flask equipped with a thermometer, add 3.3g (10.2mmol) 2,7-dibromofluorene, 0.21g (0.78mmol) tetrapropylammonium bromide and 25mL chloroform in sequence, and vacuumize Nitrogen was blown to maintain the nitrogen atmosphere, and then 5 mL of 50% potassium hydroxide aqueous solution was slowly added dropwise with a syringe. After magnetic stirring for about 30 minutes, use an ice-water bath, and after the temperature of the reaction system is constant, add 17.138 g (41 mmol) of trifluorooctyl acrylate dropwise with a syringe. After the trifluorooctyl acrylate was added dropwise, the stirring was continued for about 1 h, and the temperature was raised to 30° C. for 10 h. After the reaction, the reaction solution was poured into a separatory funnel, diluted with an appropriate amount of chloroform, ...

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Abstract

The invention belongs to the field of polymer semiconductor materials, and in particular relates to a fluorine-containing triphenylamine copolymer and a preparation method thereof. In the method of the invention, under the condition that a phase transfer catalyst and a solvent exist, 2,7-dibromofluorene is injected into an alkali solution for reaction, and then a fluorine-containing acrylate is added dropwise for reaction to obtain a dibromofluorine-containing fluorene monomer. Then react dibromofluorine-containing fluorene monomer with diboronic acid ester and dibromo in the presence of catalyst, ligand, weak base and solvent, then add phenylboronic acid for reaction, and finally add bromobenzene for reaction, The fluorine-containing triphenylamine copolymer is synthesized, and the preparation method of the fluorine-containing fluorene monomer is simple. The fluorine-containing triphenylamine copolymer thus obtained not only has the excellent photoelectric properties of the triphenylamine copolymer, but also has excellent hydrophobicity.

Description

technical field [0001] The invention belongs to the field of polymer semiconductor materials, and in particular relates to a fluorine-containing triphenylamine copolymer and a preparation method thereof. Background technique [0002] Triphenylamine polymers not only have good electron-donating ability and good hole-transporting ability, but also have the unique advantages of polymer materials. The luminescent color and electronic structure of the material can be adjusted through chemical modification. In addition, the triphenylamine polymer semiconductor material also has excellent machinability, good stability and film-forming properties. [0003] In the existing triphenylamine copolymers, triphenylamine is mainly modified with aliphatic substituents to increase the solubility and processability of the copolymers. However, the hydrophobicity of these substituents is still insufficient, and the application of triphenylamine copolymerization in organic electronic devices is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07C67/347C07C69/65
CPCC07C67/347C08G61/121C08G2261/122C08G2261/146C08G2261/312C08G2261/3142C08G2261/3162C08G2261/411C07C2603/18C07C69/65
Inventor 李坚贾正任强汪称意
Owner CHANGZHOU UNIV