Diamine containing phenoxazine and amide structures and polyimide thereof

A polyimide and phenoxazine technology, applied in the field of material science, can solve the problems of limiting the wide application of polyimide, insufficient antibacterial properties, easy to break and fall off, etc., and achieve high glass transition temperature and thermal stability. , improve functional diversity, and promote the effect of close stacking

Inactive Publication Date: 2020-04-28
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polyimide has extremely strong heat resistance, good mechanical properties and dimensional stability, and is one of the best choices for flexible OLED substrates or packaging materials, while the barrier properties of traditional commercial polyimide films cannot meet the needs of flexible displays. Due to the packaging requirements of devices, the methods of multi-layer composite, coating and inorganic nano-modification still have shortcomings in improving the barrier performance. The high-barrier film used in multi-layer composite has poor heat resistance and low stability; the coating film It affects its flexibility, and the surfa

Method used

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  • Diamine containing phenoxazine and amide structures and polyimide thereof
  • Diamine containing phenoxazine and amide structures and polyimide thereof
  • Diamine containing phenoxazine and amide structures and polyimide thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] This example provides

[0048]Synthesis of N3,N7-bis(4-aminophenyl)-10H-phenoxazine-3,7-dicarboxamide:

[0049]

[0050] (1) Synthesis of intermediate 10H-phenoxazine-3,7-dicarbonitrile:

[0051] Add 3.41g (0.01mol) of 3,7-dibromo-10H-phenoxazine, 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 add 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, Removal of the solvent under reduced pressure gave the crude product as a brown solid which was triturated with methanol to give the intermediate. The intermediate structure is as follows:

[0052]

[0053] (2) Synthesis of intermediate 10H-phenoxazine-3,7-dicarboxylic acid:

[0054] Add 2.33g (0.01mol) of 10H...

Embodiment 2

[0065] This example provides the synthesis of N3, N7-bis(5-aminothiophen-2-yl)dibenzo[b,d]furan-3,7-dicarboxamide:

[0066]

[0067] (1) Synthesis of intermediate 10H-phenoxazine-2,7-dicarbonitrile:

[0068] Add 3.41g (0.01mol) of 2,7-dibromo-10H-phenoxazine, 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 add 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, Removal of the solvent under reduced pressure gave the crude product as a brown solid which was triturated with methanol to give the intermediate. The intermediate structure is as follows:

[0069]

[0070] (2) Synthesis of intermediate 10H-phenoxazine-2,7-dicarboxylic acid:

[0071] Add 2.33g (0.01mol) of...

Embodiment 3

[0082] This example provides N2,N8-bis(7-aminodibenzo[b,d]furan-3-yl)-10H-phenoxazine-2,8-dicarboxamide:

[0083]

[0084] (1) Synthesis of intermediate 10H-phenoxazine-2,8-dicarbonitrile:

[0085] Add 3.41g (0.01mol) of 2,8-dibromo-10H-phenoxazine, 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 add H 2 O (180mL), HCl (60mL) and FeCl 3 (4.19g, 25.8mmol) was poured into the reaction solution and stirred for 1h, cooled to room temperature, filtered to obtain a brown precipitate, and washed with water, the resulting solid was re-dissolved in dichloromethane and washed with water, and the solvent was removed under reduced pressure to obtain the crude product as a brown solid , which was triturated with methanol to afford the intermediate. The intermediate structure is as follows:

[0086]

[0087] (2) Synthesis of intermediate 10H-phenoxazine-2,8-dicarboxylic acid:

[0088]Add 2.33g (0.01mol) of...

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Abstract

The invention discloses diamine containing phenoxazine and amide structures and polyimide thereof. The preparation method comprises the following steps: converting halogen atoms of dihalogenated phenoxazine into cyano groups, carrying out hydrolysis to obtain a dicarboxylic acid monomer, then carrying out acylating chlorination, grafting a nitro-containing group through an amide reaction, finallycarrying out reduction to obtain a diamine monomer containing the phenoxazine and the amide structures, and polymerizing the prepared diamine monomer with dianhydride to obtain polyimide containing the phenoxazine and the amide structures. The planar rigid structure of the phenoxazine and the amide polar group are creatively introduced into a polyimide main chain, the planar rigid structure is beneficial to regular stacking of molecular chains and induction of polymer crystallization, and polar groups can enhance the hydrogen-bond interaction of the molecular chains and promote tight stackingof the molecular chains so that polyimide has excellent barrier property, higher glass-transition temperature and thermal stability, lower thermal expansion coefficient and good antibacterial property.

Description

technical field [0001] The invention relates to the technical field of material science, more specifically, to a diamine containing a phenoxazine and an amide structure and a polyimide thereof. Background technique [0002] Polyimide is one of the organic polymer materials with the best comprehensive performance. It has high and low temperature resistance, excellent mechanical properties, good stability, flame retardancy and non-toxic properties. Whether it is used as a structural material or as a functional Its huge application prospects have been fully recognized. As a promising polymer material, polyimide is being widely used in insulating materials and structural materials. In terms of functional materials, it is emerging, and its potential is still being explored. [0003] FOLED is one of the technologies with great development prospects. It can realize flexible display, can prepare foldable and curved displays, and is thinner and more impact-resistant than rigid glas...

Claims

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Application Information

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IPC IPC(8): C07D265/38C07D413/14C08G73/10C08L79/08C08J5/18
CPCC07D265/38C07D413/14C08G73/1007C08G73/1085C08J5/18C08J2379/08
Inventor 谭井华刘亦武贺盼赵先清
Owner HUNAN UNIV OF TECH
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