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Rigid alicyclic ketone anhydride compound as well as preparation method and application thereof

A technology of alicyclic ketone anhydrides and compounds, which is applied in the field of rigid alicyclic ketone anhydride compounds and their preparation, can solve the problems of inability to perform roll-to-roll process, lack of flexible substrate materials, high thermal expansion coefficient, etc., and achieve improved glass transition temperature and Thermal stability, wide application value, effect of improving optical performance

Active Publication Date: 2022-02-18
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ultra-thin glass has excellent optical properties, heat resistance and barrier properties, and has a low thermal expansion coefficient (good dimensional stability), but it is brittle and fragile and cannot be used in roll-to-roll processes; metal foil has excellent barrier properties and Heat resistance, but its thermal expansion coefficient is high and opaque; the above engineering plastics all have high transmittance (T%>85%), but they all have a fatal shortcoming: low heat resistance temperature (Tg<150°C ), poor dimensional stability (linear coefficient of thermal expansion CTE)
[0006] In summary, the existing technology still lacks a flexible substrate material that satisfies the characteristics of optical performance, thermal stability and dimensional stability.

Method used

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  • Rigid alicyclic ketone anhydride compound as well as preparation method and application thereof
  • Rigid alicyclic ketone anhydride compound as well as preparation method and application thereof
  • Rigid alicyclic ketone anhydride compound as well as preparation method and application thereof

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Effect test

Embodiment 1

[0050] A kind of preparation method of the dianhydride compound of rigid alicyclic containing trifluoromethyl group and benzene ring side group structure, comprises the following steps:

[0051] (1) Put 2,3,6,7-tetramethylanthracene-9,10-dione (10.00g, 37.83mmol, 1.00 equivalent) into a 1000mL three-necked flask, and add CsF (57.5 mg, 0.043mmol, 0.01 equivalent), add 500mL of anhydrous tetrahydrofuran. Cool the reaction solution to -10°C, stir for 10 minutes, add trimethyl(trifluoromethyl)silane (6 mL, 39.79 mmol, 1 equiv), continue stirring for 10 minutes, then slowly heat the reaction mixture to 10°C . And stirring was continued for 3 hours. After the reaction was complete, the reaction mixture was filtered, and the filter cake was rinsed with dichloromethane (50 mL / 3 times). The crude product was separated and purified by silica gel (petroleum ether / ethyl acetate: 10 / 1) column chromatography to obtain the white solid product 2,3,6,7-tetramethyl-10-(trifluoromethyl)-10-( ...

Embodiment 2

[0059] Yield 63%.

Embodiment 3

[0061] Yield 66%.

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Abstract

The invention belongs to the technical field of new materials, and particularly relates to a rigid alicyclic ketone anhydride compound and a preparation method and application thereof. The molecular structure of the rigid alicyclic ketone anhydride compound is shown in the specification, R is one of a halogen substituent, a saturated halogenated hydrocarbon substituent and the like, X1, X2 and X3 are independently one of H and the saturated halogenated hydrocarbon substituent, and halogen and halogen in halogen substituent are one of fluorine, chlorine and bromine. The rigidity of a molecular chain is maintained by introducing a rigid semi-ring structure, and on the other hand, methylene is protected by introducing trifluoromethyl and a benzene ring side group. The molecular structure of the rigid alicyclic ketone anhydride compound is asymmetric, and the asymmetric structure can improve the optical performance of polyimide. Meanwhile, the molecular chain has certain rigidity to maintain excellent thermal stability and dimensional stability. The introduction of trifluoromethyl can improve the optical performance of the film.

Description

technical field [0001] The invention belongs to the technical field of new materials, and in particular relates to a rigid alicyclic ketone anhydride compound and its preparation method and application. Background technique [0002] At present, flexible AMOLED is the development trend of the display industry. It has the characteristics of light, thin, flexible and foldable, and is the concept of healthy display. Compared with traditional liquid crystal technology, flexible OLED display has shown great progress in terms of technical level, product design concept and consumer experience. With the development of flexible OLEDs, some new requirements have been put forward for flexible substrates. More flexible substrates currently used mainly include ultra-thin glass, metal foil and polymer engineering plastics (such as: polyethylene naphthalate (PEN), polycarbonate (PC), polyethylene terephthalate Diester (PET) and other engineering plastics). They all have their pros and co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C08L79/08C08J5/18C08G73/10
CPCC07D493/04C08J5/18C08G73/1007C08G73/1039C08G73/1067C08J2379/08
Inventor 屠国力王瑶
Owner HUAZHONG UNIV OF SCI & TECH
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