Thioxanthone polyimide with high planar rigidity as well as preparation method and application thereof

A polyimide and thioxanthone technology, which is applied in the field of material science, can solve the problems of poor heat resistance of high-barrier film, influence of flexibility of coating film, easy to break and fall off, etc., and achieve excellent barrier performance and regular molecular chain arrangement. , the effect of high electron density

Inactive Publication Date: 2020-06-12
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the application, the high barrier layer film used in multi-layer composite has poor heat resistance and low stability; the coating film affects its flexibility, and the surface is not smooth, easy to break and fall off; inorganic nano-modification is the most commonly used method, The diffusion path of water vapor and oxygen molecules in the substrate is effectively extended by the sheet-like nanolayer, thereby improving its barrier performance. However, the method is based on the performance difference of the substrate, and the improvement of barrier performance is limited.

Method used

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  • Thioxanthone polyimide with high planar rigidity as well as preparation method and application thereof
  • Thioxanthone polyimide with high planar rigidity as well as preparation method and application thereof
  • Thioxanthone polyimide with high planar rigidity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] This example provides

[0044] Synthesis of N3,N6-bis(4-aminophenyl)-9-oxo-9H-thioxanthene-3,6-dicarboxamide:

[0045]

[0046] S1. Synthesis of intermediate 9-oxo-9H-thioxanthene-3,6-dicarbonitrile:

[0047] Add 3.70g (0.01mol) of 3,6-dibromo-9H-thioxanthen-9-one, 4.478g (0.05mol) of cuprous cyanide, and 50ml of dry NMP into a 500ml three-necked flask, reflux at 140°C for 24h, and then Will H 2 O (180mL), HCl (60mL) and FeCl3 (4.19g, 25.8mmol) were poured into the reaction solution and stirred for 1h, cooled to room temperature, filtered to obtain a brown precipitate, and washed with water, and the resulting solid was re-dissolved in dichloromethane and washed with water , the solvent was removed under reduced pressure to give the crude product as a brown solid, which was triturated with methanol to afford intermediate one. This intermediate one structure is as follows:

[0048]

[0049] S2. Synthesis of intermediate 9-oxo-9H-thioxanthene-3,6-dicarboxylic acid:...

Embodiment 2

[0061] This example provides

[0062] Synthesis of N2,N6-bis(5-aminothiophen-2-yl)-9-oxo-9H-thioxanthene-2,6-dicarboxamide:

[0063]

[0064] S1. Synthesis of intermediate 9-oxo-9H-thioxanthene-2,6-dicarbonitrile:

[0065] Add 3.70g (0.01mol) of 2,6-dibromo-9H-thioxanthen-9-one, 4.478g (0.05mol) of cuprous cyanide, and 50ml of dry NMP into a 500ml three-necked flask, reflux at 140°C for 24h, and then Will H 2 O (180mL), HCl (60mL) and FeCl3 (4.19g, 25.8mmol) were poured into the reaction solution and stirred for 1h, cooled to room temperature, filtered to obtain a brown precipitate, and washed with water, and the resulting solid was re-dissolved in dichloromethane and washed with water , the solvent was removed under reduced pressure to give the crude product as a brown solid, which was triturated with methanol to afford intermediate one. This intermediate one structure is as follows:

[0066]

[0067] S2. Synthesis of intermediate 9-oxo-9H-thioxanthene-2,6-dicarboxy...

Embodiment 3

[0079] This example provides a synthetic

[0080] N2,N7-bis(7-aminodibenzo[b,d]furan-3-yl)-9-oxo-9H-thioxanthene-2,7-dicarboxami-de:

[0081]

[0082] S1. Synthesis of intermediate 9-oxo-9H-thioxanthene-2,7-dicarbonitrile:

[0083] Add 3.70g (0.01mol) of 2,7-dibromo-9H-thioxanthen-9-one, 4.478g (0.05mol) of cuprous cyanide, and 50ml of dry NMP into a 500ml three-necked flask, reflux at 140°C for 24h, and then Will H 2 O (180mL), HCl (60mL) and FeCl3 (4.19g, 25.8mmol) were poured into the reaction solution and stirred for 1h, cooled to room temperature, filtered to obtain a brown precipitate, and washed with water, and the resulting solid was re-dissolved in dichloromethane and washed with water , the solvent was removed under reduced pressure to give the crude product as a brown solid, which was triturated with methanol to afford intermediate one. This intermediate one structure is as follows:

[0084]

[0085]S2. Synthesis of intermediate 9-oxo-9H-thioxanthene-2,7-d...

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Abstract

The invention discloses thioxanthone polyimide with high planar rigidity and a preparation method of the thioxanthone polyimide. According to the preparation method, halogen atoms of dihalogenated thioxanthone are converted into cyano groups, then hydrolysis and acylating chlorination are carried out and then groups containing nitro groups are grafted through an amide reaction; then diamine monomers containing thioxanthone structures are obtained through reduction, and the thioxanthone polyimide with high planar rigidity is obtained through polymerization of the diamine monomers and dianhydride. According to the invention, a large-volume planar rigid thioxanthone structure is introduced into a polyimide main chain, so that a polyimide molecular chain can be piled up more tightly, the freevolume of a polymer is reduced, and the barrier property of polyimide is effectively improved. Meanwhile, the conjugated structure of the thioxanthone structure can improve the heat resistance and oxidation resistance stability of the polymer and improve the stability of the polymer in an extreme environment.

Description

technical field [0001] The present invention relates to the technical field of material science, more specifically, relate to a kind of high planar rigid thioxanthone polyimide and its preparation method and application. Background technique [0002] OLED has superior image quality, and has the characteristics of thinness and light weight, and has become the mainstream of mobile display. With the progress of the times, flexible OLED has become the most promising new generation information display technology. However, the organic light-emitting materials in FOLEDs are particularly sensitive to the intrusion of water vapor and oxygen. Oxygen can significantly reduce the quantum efficiency of light emission and oxidize the light-emitting layer. Water vapor can hydrolyze organic layer compounds, greatly reducing stability. [0003] Polyimide has excellent properties such as high temperature resistance, high strength, and corrosion resistance. It can realize flexible display an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C07D335/16C07D409/14
CPCC07D335/16C07D409/14C08G73/1085
Inventor 谭井华刘亦武赵先清
Owner HUNAN UNIV OF TECH
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