Diamine containing phenothiazine structure and preparation method for synthesizing polyimide

A technology of polyimide and phenothiazine, which is applied in the field of material science, can solve the problems of limited barrier performance improvement, easy breakage and falling off, and cannot meet high requirements, and achieve high electron density, good rigid structure, rich and diverse functions sexual effect

Pending Publication Date: 2021-06-18
GUANGDONG GAOYI PACKAGING & PRINTING CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the barrier performance of commercial polyimide cannot meet the packaging requirements of FOLED devices. Although multi-layer film composite, film surface coating or sheet nano-modification can significantly improve its barrier performance, in 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-

Method used

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  • Diamine containing phenothiazine structure and preparation method for synthesizing polyimide
  • Diamine containing phenothiazine structure and preparation method for synthesizing polyimide
  • Diamine containing phenothiazine structure and preparation method for synthesizing polyimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] This example provides N 1 ,N 1 Synthesis of '-(10H-phenothiazine-2,8-diyl)bis(benzene-1,4-diamine):

[0043]

[0044] S1. Synthesis of intermediate 10H-phenothiazine-2,8-diamine:

[0045] Add 3.57g (0.01mol) of 2,8-dibromo-10H-phenothiazine, 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, and the solvent was removed under reduced pressure. 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:

[0046]

[0047] S2. Synthesis of intermediate N 2 ,N 8 -bis(4-nitrophenyl)-10H-phenothi...

Embodiment 2

[0053] This example provides

[0054] N 2 -(5-aminopyridin-2-yl)-N 7 -Synthesis of (6-aminopyridin-3-yl)-10H-phenothiazine-2,7-diamine:

[0055]

[0056] S1. Synthesis of intermediate 10H-phenothiazine-2,7-diamine:

[0057] Add 3.57g (0.01mol) of 2,7-dibromo-10H-phenothiazine, 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, and the solvent was removed under reduced pressure. 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:

[0058]

[0059] S2. Synthetic intermediates

[0060] N ...

Embodiment 3

[0068] This example provides N 1 ,N 1 Synthesis of '-(dibenzo[b,d]furan-2,8-diyl)bis(benzene-1,3-diamine):

[0069]

[0070] S1. Synthesis of intermediate 10H-phenothiazine-3,7-diamine:

[0071] Add 3.57g (0.01mol) of 3,7-dibromo-10H-phenothiazine, 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, and the solvent was removed under reduced pressure. 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:

[0072]

[0073] S2. Synthesis of intermediate N 3 ,N 7 -bis(3-nitrophenyl)-10H-phenot...

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PUM

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Abstract

The invention discloses diamine containing a phenothiazine structure and polyimide prepared from the diamine. The method comprises the following steps: reacting an intermediate containing phenothiazine substituted by two halogen atoms with ammonia water to convert the halogen atoms into amino groups; and grafting a nitryl-containing group through Ullmann coupling reaction, reducing to obtain the phenothiazine-structure-containing diamine monomer, and polymerizing the prepared diamine monomer with dianhydride to obtain the polyimide with the main chain containing the phenothiazine structure. A planar rigid structure and a polar group of phenothiazine 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 the hydrogen-bond interaction of the molecular chains and promote tight stacking of the molecular chains, so that polyimide has excellent barrier performance; and the glass transition temperature and the thermal stability are higher, and the thermal expansion coefficient and the antibacterial property are lower.

Description

technical field [0001] The invention relates to the technical field of material science, more specifically, to a diamine containing a phenothiazine structure and a preparation method for synthesizing polyimide. Background technique [0002] Organic light-emitting diodes (OLEDs) are flexible organic electroluminescent devices (FOLEDs) made of flexible polymer materials encapsulating OLEDs, which are lightweight, portable, bendable, foldable, and even wearable. It is an important development direction of display technology in the future. However, FOLEDs have inherent instability, low lifespan, and sensitivity to water and oxygen in OLED devices, which limit their promotion and application. The vast majority of FOLEDs use plastic as the substrate, but plastic substrates have shortcomings such as low temperature resistance, poor barrier performance, and surface flatness that is not as good as glass, which causes great difficulties in the manufacture of devices, and the manufact...

Claims

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Application Information

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IPC IPC(8): C07D279/20C07D417/14C08G73/10
CPCC07D279/20C07D417/14C08G73/1035C08G73/1053C08G73/1064C08G73/1067C08G73/1071
Inventor 谭井华刘亦武李禹慧张祥
Owner GUANGDONG GAOYI PACKAGING & PRINTING CO LTD
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