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Difluoro monomer with photoelectric activity and its use in the preparation of polyarylethersulfone polymers

A technology of high molecular polymer and double fluorine monomer, applied in the direction of organic chemistry, etc., can solve the problems of thermal stability, solubility and film-forming processability of materials, achieve good optoelectronic properties, cheap raw materials, good The effect of thermal stability

Active Publication Date: 2018-01-30
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these materials have been plagued by thermal stability, solubility, and film-forming processability.

Method used

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  • Difluoro monomer with photoelectric activity and its use in the preparation of polyarylethersulfone polymers
  • Difluoro monomer with photoelectric activity and its use in the preparation of polyarylethersulfone polymers
  • Difluoro monomer with photoelectric activity and its use in the preparation of polyarylethersulfone polymers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of polymer P1

[0042] (1) In a 500 mL two-necked flask, p-aminophenylcarbazole (15.49 g, 60 mmol) was dissolved in 120 mL of dichloromethane, and then 24 mL of triethylamine was added. While stirring under nitrogen atmosphere at room temperature, a solution of 2,6-difluorobenzoyl chloride (11.08 g, 63 mmol) in dichloromethane (120 mL) was slowly added dropwise to the above solution. The reaction was stirred at room temperature for 12h. The solution was washed with water, and the solvent was removed by evaporation. The crude product was recrystallized from a mixture of ethanol and water with a volume ratio of 10:1 to obtain white crystals, which were the product difluoromonomer M1 (20.53 g, 86%). 1H NMR (DMSO-d, rt, 300MHz): δ11.11(s, NH, 1H), 8.26-8.24(d, CH, 2H), 8.02-8.00(d, CH, 2H), 7.65(d, CH ,2H),7.62(t,CH,1H),7.44(d,CH,1H),7.41(d,CH,1H),7.33-7.30(t,CH,2H),7.29-7.26(t,CH, 2H).

[0043] (2) Difluoromonomer M1 (3.984g, 10mmol), bisp...

Embodiment 2

[0045] Embodiment 2: the preparation of polymer P2 series

[0046] (1) Dissolve p-aminophenyl bis-tert-butylcarbazole (18.50 g, 50 mmol) in 100 mL of dichloromethane in a 500 mL two-necked flask, and then add 20 mL of triethylamine. While stirring under nitrogen atmosphere at room temperature, a solution of 2,6-difluorobenzoyl chloride (9.15 g, 52 mmol) in dichloromethane (100 mL) was slowly added dropwise to the above solution. The reaction was stirred at room temperature for 12h. The solution was washed with water, and the solvent was removed by evaporation. The crude product was recrystallized from a mixture of ethanol and water with a volume ratio of 10:1 to obtain white crystals which were the product difluoromonomer M2 (23.62 g, 92%). 1H NMR(DMSO-d,rt,300MHz):δ11.07(s,NH,1H),8.29(d,CH,2H),7.98-7.95(d,CH,2H),7.66(d,CH,2H ),7.62(t,CH,1H),7.59(d,CH,1H),7.49(d,CH,1H),7.33-7.30(t,CH,2H),7.29-7.26(t,CH,2H) , 1.42 (s, CH, 9H).

[0047] (2) Put bisfluoromonomer M2, bisphenol...

Embodiment 3

[0050] Embodiment 3: the preparation method of polymer P7

[0051] (1) In a 500 mL two-necked flask, p-aminotriphenylamine (13.02 g, 50 mmol) was dissolved in 100 mL of dichloromethane, and then 20 mL of triethylamine was added. While stirring under nitrogen atmosphere at room temperature, a solution of 2,6-difluorobenzoyl chloride (9.15 g, 52 mmol) in dichloromethane (100 mL) was slowly added dropwise to the above solution. The reaction was stirred at room temperature for 12h. The solution was washed with water, and the solvent was removed by evaporation. The crude product was recrystallized from a mixture of ethanol and water with a volume ratio of 10:1 to obtain light blue crystals which were the product difluoromonomer M7 (18.03 g, 90%). 1H NMR (DMSO-d, rt, 300MHz): δ10.79(s, NH, 1H), 7.65(d, CH, 1H), 7.62(d, CH, 2H), 7.58-7.56(m, CH, 4H ), 7.31-7.22 (m, CH, 6H), 7.05-7.00 (m, CH, 4H).

[0052] (2) Difluoromonomer M7 (3.20g, 8mmol), bisphenol A (4.56g, 20mmol), 4,4'-dic...

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Abstract

The invention relates to a 2,6-difluoro benzoyl chloride difluoro monomer with photoelectric activity and application of the monomer to preparation of a polyarylether sulphone high-molecular polymer containing photoelectric activity units in the side chain, and belongs to the technical field of high-molecular materials. Various compounds of a photoelectric activity structure and with monoamino groups and 2,6-difluoro benzoyl chloride are subjected to amide condensation to obtain the novel difluoro monomer with photoelectric activity; the prepared bifluoro monomer, dual-halogen-substituted diphenyl sulfone and a bisphenol monomer are subjected to ternary polymerization to obtain a series of polyarylether sulphone copolymers with different contents of photoelectric activity side chains by adjusting the feeding ratio of dual-halogen-substituted diphenyl sulfone to the bisphenol monomer. The polyarylether sulphone material prepared through the method has excellent photoelectric activity, outstanding heat stability and good solubility, and has potential wide application value in the photoelectricity fields such as hole transport, electrochromism, electroluminescence, information storage and output and solar cells, and the machinability of the polyarylether sulphone material is improved.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, in particular to a class of photoelectrically active 2,6-difluorobenzamide difluoro monomer containing photoelectrically active functional groups such as carbazole, triphenylamine, anthraquinone and azo, and the monomer The application of the body in the preparation of polyarylethersulfone polymers containing photoelectrically active functional units in the side chain. Background technique [0002] The widespread application of information system transmission and display technology marks that mankind has opened the door to the "information age" in the early 21st century. Since then, human life has undergone revolutionary changes and has benefited a lot from it. The rapid development of information industry technology requires the continuous improvement of technology and the development and innovation of theoretical knowledge. The development of new materials can not only provide a basis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G75/23C07D209/86C07D209/88C07C233/80C07C233/76C07C245/08
CPCC07C233/76C07C233/80C07C245/08C07D209/86C07D209/88C08G75/23
Inventor 姜振华韩韫韬陈峥孙大野林英健
Owner JILIN UNIV
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