Polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof

A dihydroacridine and polyimide technology, applied in the field of material science, can solve problems such as inability to meet, and achieve the effects of improving barrier properties, compact stacking, high glass transition temperature and thermal stability

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

The above methods can significantly improve the barrier performance of polyimide, but the barrier improvement can only be limited on the original basic material, and cannot meet the actual needs of FOLED

Method used

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  • Polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof
  • Polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof
  • Polyimide containing 9,10-dihydroacridine structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] This example provides the synthesis of N1,N1'-(9,10-dihydroacridine-3,6-diyl)bis(benzene-1,4-diamine):

[0040]

[0041] S1. Synthesis of intermediate 9,10-dihydroacridine-3,6-diamine:

[0042] Add 3.39g (0.01mol) of 3,6-dibromo-9,10-dihydroacridine, an appropriate amount of cuprous oxide, 50ml of NMP, and 13ml of ammonia water (29%, 0.2mol) into a 200ml pressure bottle, under argon protection, and react at 100°C After the reaction is completed, the reaction solution is poured into ice water, extracted with dichloromethane, and the solvent is removed under reduced pressure. The product uses dichloromethane:n-hexane=2:1 (volume ratio) as the mobile phase and silica gel as the stationary phase After chromatographic purification, the product was collected and spin-dried, and dried in vacuum at 80°C for 24 hours to obtain an intermediate. The intermediate structure is as follows:

[0043]

[0044] S2. Synthetic intermediate N3, N6-bis(4-nitrophenyl)-9,10-dihydroacri...

Embodiment 2

[0050] This example provides the synthesis of N6-(5-aminopyridin-2-yl)-N2-(6-aminopyridin-3-yl)-9,10-dihydroacridine-2,6-diamine:

[0051]

[0052] S1. Synthesis of intermediate 9,10-dihydroacridine-2,6-diamine:

[0053] Add 3.39g (0.01mol) of 2,6-dibromo-9,10-dihydroacridine, an appropriate amount of cuprous oxide, 50ml of NMP, and 13ml of ammonia water (29%, 0.2mol) into a 200ml pressure bottle, under argon protection, and react at 100°C After the reaction is completed, the reaction solution is poured into ice water, extracted with dichloromethane, and the solvent is removed under reduced pressure. The product uses dichloromethane:n-hexane=2:1 (volume ratio) as the mobile phase and silica gel as the stationary phase After chromatographic purification, the product was collected and spin-dried, and dried in vacuum at 80°C for 24 hours to obtain an intermediate. The intermediate structure is as follows:

[0054]

[0055] S2. Synthetic intermediate N6-(5-nitropyridin-2-y...

Embodiment 3

[0061] This example provides the synthesis of N1,N1'-(9,10-dihydroacridine-2,7-diyl)bis(benzene-1,3-diamine):

[0062]

[0063] S1 synthetic intermediate 9,10-dihydroacridine-2,6-diamine:

[0064] Add 3.41g (0.01mol) of 3,7-dibromo-10H-phenoxazine, an appropriate amount of cuprous oxide, 50ml of NMP, and 13ml of ammonia water (29%, 0.2mol) into a 200ml pressure bottle, under argon protection, and react at 100°C. After the reaction was completed, the reaction solution was poured into ice water, extracted with dichloromethane, the solvent was removed under reduced pressure, and the product was purified by column chromatography using dichloromethane:n-hexane=2:1 (volume ratio) as the mobile phase and silica gel as the stationary phase. , the product was collected and spin-dried, and dried in vacuum at 80°C for 24h to obtain an intermediate. The intermediate structure is as follows:

[0065]

[0066] S2. Synthesis of intermediate N2, N7-bis(3-nitrophenyl)-9,10-dihydroacrid...

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Abstract

The invention discloses polyimide containing a 9,10-dihydroacridine structure, and a preparation method and an application thereof. The preparation method comprises the following steps: reacting an intermediate containing 9,10-dihydroacridine substituted by two halogen atoms with ammonia water to convert the halogen atoms into amino groups; and grafting with a nitro-containing group through a Ullmann coupling reaction, then performing reduction to obtain a 9,10-dihydroacridine structure-containing diamine monomer, and then polymerizing the prepared diamine monomer with dianhydride to obtain the polyimide containing the 9,10-dihydroacridine structure. A planar rigid structure 9,10-dihydroacridine and a 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 the polar group can enhance hydrogen bond interaction of the molecular chains and promote closestacking of the molecular chains, so that polyimide has excellent barrier property, high glass-transition temperature and thermal stability and low thermal expansion coefficient.

Description

technical field [0001] The invention relates to the technical field of material science, and more specifically, to a polyimide containing a 9,10-dihydroacridine structure and a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) are self-illuminating, high brightness (more than 10 5 cd / m 2 ), ultra-thin and light weight, fast response (more than 1000 times of LCD), wide viewing angle (close to 180°), low driving voltage, wide operating temperature range, all solid-state and other advantages, it is considered to be the most likely to replace liquid crystal display (LCD ) of a new generation of displays. The flexible organic electroluminescent device (FOLED) made of flexible polymer material encapsulating OLED has the characteristics of light weight, easy to carry, bendable, foldable, and even wearable. It is an important development direction of future display technology. [0003] However, FOLED has problems of in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C07D219/08
CPCC07D219/08C08G73/1039C08G73/1067C08G73/1085
Inventor 刘亦武谭井华赵先清周栋
Owner HUNAN UNIV OF TECH
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