High-barrier polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof

A technology of dihydroacridine and polyimide, which is applied in the field of material science to achieve the effect of high planarity, promotion of close packing, and regular arrangement of molecular chains

Inactive Publication Date: 2020-04-21
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few studies on the high barrier intrinsic polyimides provided, therefore, it is necessary to develop a variety of intrinsic polyimides with high barrier properties

Method used

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  • High-barrier polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof
  • High-barrier polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof
  • High-barrier polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] This example provides

[0049] Synthesis of N2,N7-bis(4-aminophenyl)-9,10-dihydroacridine-2,7-dicarboxamide:

[0050]

[0051] S1. Synthesis of intermediate 9,10-dihydroacridine-2,7-dicarbonitrile:

[0052] Add 3.39g (0.01mol) of 2,7-dibromo-9,10-dihydroacridine, 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 (180 mL), HCl (60 mL) and FeCl3 (4.19 g, 25.8 mmol) were poured into the reaction solution and stirred for 1 h, cooled to room temperature, filtered to obtain a brown precipitate, and washed with water, and the obtained solid was redissolved 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 give the intermediate. The intermediate structure is as follows:

[0053]

[0054] S2. Synthesis of intermediate 9,10-dihydroacridine-2,7-dicarboxylic acid:

[005...

Embodiment 2

[0067] This example provides

[0068] Synthesis of N2,N6-bis(5-aminothiophen-2-yl)-9,10-dihydroacridine-2,6-dicarboxamide:

[0069]

[0070] S1. Synthesis of intermediate 9,10-dihydroacridine-2,6-dicarbonitrile:

[0071] Add 3.39g (0.01mol) of 2,6-dibromo-9,10-dihydroacridine, 2.7624g (0.05mol) of cyanocopper, and 50ml of dry NMP into a 500ml three-neck flask, reflux at 140°C for 24h, then add water (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, the resulting solid was re-dissolved in dichloromethane and washed with water, and the solvent was removed under reduced pressure The crude product was obtained as a brown solid which was triturated with methanol to give the intermediate. The intermediate structure is as follows:

[0072]

[0073] S2. Synthesis of intermediate 9,10-dihydroacridine-2,6-dicarboxylic acid:

[0074...

Embodiment 3

[0087] This example provides a synthetic

[0088] N3,N6-bis(7-aminodibenzo[b,d]furan-3-yl)-9,10-dihydroacridine-3,6-dicarboxamide:

[0089]

[0090] S1. Synthesis of intermediate 9,10-dihydroacridine-3,6-dicarbonitrile:

[0091] Add 3.39g (0.01mol) of 3,6-dibromo-9,10-dihydroacridine, 2.7624g (0.05mol) of cyanocopper, and 50ml of dry NMP into a 500ml three-neck flask, reflux at 140°C for 24h, then add water (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, the resulting solid was re-dissolved in dichloromethane and washed with water, and the solvent was removed under reduced pressure The crude product was obtained as a brown solid which was triturated with methanol to give the intermediate. The intermediate structure is as follows:

[0092]

[0093] S2. Synthesis of intermediate 9,10-dihydroacridine-3,6-dicarboxylic acid: ...

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Abstract

The invention discloses a high-barrier polyimide containing a 9,10-dihydroacridine structure, and a preparation method and an application thereof. The preparation method comprises the following steps:converting halogen atoms of dihalogenated 9,10-dihydroacridine into cyano groups, hydrolyzing to obtain a dicarboxylic acid monomer, performing acylating chlorination, grafting with a nitro-containing groups through an amidation reaction, performing reduction to obtain a diamine monomer, and polymerizing the prepared diamine monomer with dianhydride to obtain the polyimide containing the 9,10-dihydroacridine structure. The diamine containing the 9,10-dihydroacridine structure has a planar rigid structure and also contains many structures capable of generating hydrogen bonds, and polyimide prepared by taking the diamine as a monomer has the advantages of tight molecular chain stacking, small free volume and high barrier property.

Description

technical field [0001] The invention relates to the technical field of material science, and more specifically, to a high-barrier polyimide containing a 9,10-dihydroacridine structure and a preparation method and application thereof. Background technique [0002] Flexible organic electroluminescent device (FOLED) is a kind of flexible substrate material, which has the characteristics of light weight, easy to carry, bendable, foldable, and even wearable. It is an important development direction of future display technology. However, FOLED has problems of insufficient stability and lifetime, which limits its popularization and application. When manufacturing FOLEDs, since the manufacturing process temperature of thin film transistors (TFTs) is much higher than the glass transition temperature of general polymers, the TFT manufacturing process is difficult to complete, which greatly limits the improvement of FOLED performance. Generally, the substrate material is required. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C07D219/04
CPCC07D219/04C08G73/1039C08G73/1064C08G73/1067C08G73/1071
Inventor 刘亦武谭井华赵先清周栋
Owner HUNAN UNIV OF TECH
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