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Polyimide containing benzoxazole and carbazole structures as well as preparation method and application of same

A polyimide and benzoxazole technology, applied in the field of material science, can solve the problem of reducing the number of charge transfer complexes, and achieve the effects of reducing the charge transfer effect, high luminous intensity, and good thermal stability

Active Publication Date: 2020-05-08
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this type of polyimide, there are still strong interactions between the main chains, between the side groups or between the main chain and the side groups, the number of charge transfer complexes cannot be reduced, and the charge transfer effect is still strong.

Method used

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  • Polyimide containing benzoxazole and carbazole structures as well as preparation method and application of same
  • Polyimide containing benzoxazole and carbazole structures as well as preparation method and application of same
  • Polyimide containing benzoxazole and carbazole structures as well as preparation method and application of same

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preparation example Construction

[0045] Wherein, the preparation method of the group Y of the diamine compound containing carbazole and benzoxazole structure shown in general structural formula Y-1 or Y-2 comprises the following steps:

[0046] (1) Utilize substituted p-fluorophenylboronic acid and 2-chlorobenzoxazole to couple through Suzuki reaction, obtain 2-substituted phenylbenzoxazole structure, its general structural formula is as structural formula (2):

[0047]

[0048] (2) Utilize the active hydrogen grafting step (1) in the dihalogenated carbazole monomer carbazole to obtain a dihalogenated structure containing a carbazole benzoxazole structure, and its general structural formula is as structural formula (3);

[0049]

[0050] Where X can be fluorine, chlorine, bromine or iodine.

[0051] (3) The dihalogenated structure obtained in step (2) and 4-aminophenylboronic acid or 3-aminophenylboronic acid are prepared by Suzuki coupling reaction to prepare diamine, wherein, reacting with 4-aminophen...

Embodiment 1

[0058] (1) Preparation of diamine monomer

[0059] a. Synthesis of intermediate 2-(4-fluorophenyl)-benzoxazole

[0060] Add 7.65g (50mmol) of 2-chlorobenzoxazole, 7.0g (50mmol) of p-fluorophenylboronic acid, and 10.28g of potassium carbonate (75mmol) into a 250mL three-necked round-bottomed flask, and add 100mL of tetrahydrofuran solution and 50mL of deionized water , magnetically stirred and introduced argon gas, then added 0.05g tetrakistriphenylphosphine palladium, raised the temperature to 90°C and stirred for 12 hours, then cooled, poured the reaction solution into water for precipitation, extracted with ethyl acetate, and separated the layers to obtain an organic layer , spin-dried, and purified by column chromatography to obtain 7.67 g of white product 2-(4-fluorophenyl)-benzoxazole, with a yield of about 72%, and its structural formula is as follows:

[0061]

[0062] b. Synthesis of intermediate substituted dibromocarbazole derivatives

[0063] Add 6.39g (30mmol)...

Embodiment 2

[0075] (1) Synthesis of meta-substituted target diamine monomer 2

[0076] 5.18g (10mmol) of substituted dibromocarbazole derivatives prepared in step b of Example 1, 6.64g (24mmol) of potassium carbonate and 6.58g (24mmol) of 3-aminophenylboronic acid were added to a 250mL double-necked round-bottomed flask, Add 80mL tetrahydrofuran, 40mL deionized water, magnetically stir and pass through argon protection, then add a catalytic amount of tetrakistriphenylphosphine palladium, heat up to 90°C and react for 24h, cool to room temperature, pour the reaction solution into water for precipitation, After filtration, it was fully washed with methanol, and after drying, it was purified by column chromatography to obtain 4.07 g of the target diamine monomer with a yield of about 75%. Its structural formula is as follows:

[0077]

[0078] (2) At -10°C, add 2.1688g (4mmol) of the diamine monomer prepared in step (1), 3.2038g (16mmol) of 4,4'-diaminodiphenyl ether and 24.4mL of N-N dim...

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Abstract

The invention discloses polyimide containing benzoxazole and carbazole structures as well as a preparation method and application of the same. The compound is prepared from dihalogenated carbazole, wherein active hydrogen in monomer carbazole is grafted with a benzoxazole-containing structural unit, a novel functional diamine monomer with benzoxazole and carbazole structures is prepared through Suzuki reaction or direct ammoniation with liquid ammonia, and then the diamine compound is used for synthesizing high-performance and functional polymers such as novel polyimide, polyamide and polyesterimide. The polyimide material synthesized from the diamine monomer is high in thermal stability, and has obvious fluorescence characteristics and high luminous intensity.

Description

technical field [0001] The invention relates to the technical field of material science, in particular to a polyimide containing benzoxazole and carbazole structures, a preparation method and application thereof. Background technique [0002] Polyimide is a class of high-performance polymers containing imide rings in the main chain. It is one of the best heat-resistant varieties among engineering plastics that have been industrialized. It has outstanding properties that other materials cannot match, such as high Mechanical strength, high and low temperature resistance, chemical corrosion resistance, good dimensional stability and excellent film-forming properties, etc., so it has a wide range of applications in aerospace, microelectronics, military, liquid crystal display and other fields. On the other hand, with the advancement of display technology, organic light-emitting diodes have become a popular technology in the past ten years due to their advantages such as active l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C09K11/06C08J5/18C08L79/08
CPCC08G73/1085C08G73/1078C08G73/1042C09K11/06C08J5/18C09K2211/1466C09K2211/1475C08J2379/08
Inventor 张艺吴慧焱龙禹波陈玥琪蒋星池振国刘四委许家瑞
Owner SUN YAT SEN UNIV
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