Polyimide with high thermal dimensional stability, preparation method therefor and application of polyimide

A technology of polyimide and polyamic acid, which is applied in the field of high molecular polymers, can solve the problems that cannot satisfy the processing and application of flexible display substrates

Active Publication Date: 2019-08-20
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there are still few reports on polyimides with high glass transition temperature and low thermal expansion coefficient at high temperature and their preparation methods that can meet the above requirements at the same time.
However, most of the reported polyimide films have thermal expansion coefficients between 40-80ppm / k, which cannot meet the requirements of flexible display substrate processing applications.

Method used

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  • Polyimide with high thermal dimensional stability, preparation method therefor and application of polyimide
  • Polyimide with high thermal dimensional stability, preparation method therefor and application of polyimide
  • Polyimide with high thermal dimensional stability, preparation method therefor and application of polyimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Example 1. N, N'-bis(5-nitropyridin-2-yl) p-benzamide

[0101]

[0102] Add 30.0g of 5-nitro-2-aminopyridine and 150mL of pyridine into a 500mL two-necked flask, and stir at room temperature for 5min until the solid dissolves. Dissolve 21.89g of terephthaloyl chloride in 100mL of tetrahydrofuran, and slowly drop it into the two-necked flask within 2 hours. After stirring and reacting at room temperature for 36 h, the precipitated solid was filtered, washed with water, and refluxed in 300 mL of methanol for 1 h. Then the solid was filtered and dried to obtain 34.5 g of white solid with a yield of 78%. 1 H NMR (400MHz, CDCl 3 , ppm): δ11.73(s,2H), 9.22(d,2H), 8.66(dd,2H), 8.41(dd,2H), 8.13(d,4H). 13 C NMR (151MHz, CDCl 3 , ppm): δ 163.95, 152.05, 141.33, 139.62, 133.72, 129.47, 124.89, 114.79.

Embodiment 2

[0103] Example 2. N, N'-bis(5-aminopyridin-2-yl) p-benzamide

[0104]

[0105] Add 25.0g of N,N'-bis(5-nitropyridin-2-yl)p-benzamide and 100mL of N,N'-dimethylacetamide into a 500mL two-neck flask, stir at 80°C for 30min until the solid dissolves . Add 3g of 10wt% Pd / C, 50mL of methanol to the bottle, slowly add 40mL of 80wt% hydrazine hydrate dropwise, and release gas. After no more gas is released, stir at 80°C for 6h. Pd / C was filtered off with celite to obtain a clear yellow filtrate, which was concentrated and poured into acetone. The precipitated solid was filtered, refluxed repeatedly in acetone, and dried to obtain 18 g of a yellow solid with a yield of 85%. 1 H NMR (400MHz, CDCl 3, ppm): δ10.47(s,2H),8.02(s,4H),7.79(d,2H),7.72(d,2H),6.99(dd,2H),5.18(s,4H). 13 C NMR (101 MHz, DMSO-d 6 , ppm) 164.60, 142.53, 142.07, 137.37, 133.75, 128.05, 122.65, 116.42.

Embodiment 3

[0106] Example 3.4-nitro-N-(5-nitropyridin-2-yl)benzamide

[0107]

[0108] Add 20.0g of 5-nitro-2-aminopyridine to a 500mL two-necked flask, 150mL of pyridine, and stir at room temperature for 5min until the solid dissolves. 26.68g of 4-nitrobenzoyl chloride was dissolved in 100mL of tetrahydrofuran, and slowly added dropwise into the two-necked flask within 2h. After stirring and reacting at room temperature for 36 h, the precipitated solid was filtered, washed with water, and refluxed in 300 mL of methanol for 1 h. Then the solid was filtered and dried to obtain 31.5 g of a white solid with a yield of 76%. 1 H NMR (400MHz, CDCl 3 ,ppm): δ11.89(s,1H),9.22(d,1H),8.66(dd,1H),8.41(d,1H),8.31(d,2H),8.20(d,2H). 13 C NMR (101MHz, CDCl 3 , ppm): δ152.76, 145.33, 140.08, 136.13, 132.72, 131.72, 127.90, 124.38, 119.20, 111.89.

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Abstract

The invention discloses polyimide with high thermal dimensional stability, a preparation method therefor and an application of the polyimide. The polyimide disclosed by the invention has a structure represented by a formula I. After a polyimide film is prepared from the polyimide disclosed by the invention, excellent heat resistance, an ultralow thermal expansion coefficient and relatively good mechanical properties and flexibility are shown, and the technical requirements of flexible display industry on development of flexible substrate materials can be met; and the polyimide is applied to production of flexible display devices, and meanwhile, a way of think of designing of a novel monomeric compound is provided for developing high-performance materials.

Description

technical field [0001] The invention relates to the field of polymers, in particular to a polyimide with high thermal dimensional stability and its preparation method and application. Background technique [0002] In recent years, flexible display devices such as bendable and foldable devices have become an important development direction of electronic information and display technology. Flexible electronic products such as flexible organic light-emitting displays (Flexible OLED) are considered to gradually replace traditional hard electronic display devices, and are used in various fields such as mobile phones, watches, vehicles, and medical care. Foreign market research predicts that by 2020, the flexible OLED market will reach 1.2 billion US dollars, while the entire flexible display market will reach 42 billion US dollars, accounting for about 16% of the overall flat panel display market, which is an industry with great development potential. [0003] The flexibility of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/14C08J5/18C08L79/08
CPCC08G73/14C08J5/18C08J2379/08
Inventor 房强王元强孙晶
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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