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A kind of polyimide precursor composition and its preparation method and application

A polyimide precursor and composition technology, applied in the field of flexible materials, can solve the problems of low glass transition temperature, glass transition temperature of polyimide flexible substrate, heat resistance, dimensional stability and mechanical properties reduction, Reduce the film thickness of slurry and other problems, to meet the requirements of manufacturing process and subsequent use, improve the stability of molecular structure and molecular weight, and the effect of excellent heat resistance stability

Active Publication Date: 2022-07-12
FUYANG XINYIHUA MATERIAL TECH +1
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0004] Usually, the polyamic acid solution prepared by polymerization has a relatively high viscosity, reaching tens of thousands to hundreds of thousands of centipoises, which cannot meet the coating requirements of the panel production line process
Most of the prior art reduces the viscosity of the resin solution by reducing the molecular weight or solid content of the polyamic acid resin, but reducing the molecular weight will affect the glass transition temperature, heat resistance, dimensional stability and mechanical properties of the polyimide flexible substrate. Significantly reduce the impact; reducing the solid content will lead to a decrease in the film thickness of the slurry, a longer film forming time, and an increase in the amount of organic solvents
[0005] At present, many researchers focus on the research and development of polyimide materials. For example, CN104582960A discloses a transparent polyimide laminate and a manufacturing method thereof. The preparation method of the transparent polyimide laminate is as follows: first Coating a solution containing a polyimide precursor on a support substrate, and then heating and curing to obtain a laminate; wherein, the solution containing a polyimide precursor contains a tetracarboxylic acid component and a diamine component The resulting polyimide precursor and solvent; the glass transition temperature of the transparent polyimide layer obtained by the above method is more than 260 ° C, with good light transmittance; but the glass of the polyimide layer The transition temperature is lower than 300°C, which makes it difficult to meet the ultra-high temperature (>400°C) requirements in the processing of flexible display devices
CN109796592A discloses a polyimide precursor, a transparent polyimide film and a preparation method thereof, wherein the preparation raw materials of the polyimide precursor include nano silicon dioxide and dianhydride modified by aniline groups; wherein, The transparent polyimide film modified by nano-silica has better thermal stability, and can be used as a cover plate or substrate material in the field of flexible display; however, the glass transition temperature of the transparent polyimide film is low At 410°C, it is difficult to meet the thermal stability requirements during the processing of display devices

Method used

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  • A kind of polyimide precursor composition and its preparation method and application
  • A kind of polyimide precursor composition and its preparation method and application
  • A kind of polyimide precursor composition and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0071] Preparation of compound C-1

[0072]

[0073] Step 1: Synthesis of Intermediate Compound A1

[0074] 34.5 g of 6-nitro-3-bromo-phthalic xylene and 6 g of NaOH were added to 550 mL of pyridine (py) and 280 mL of pure water, added and stirred, and the system was heated to reflux temperature. Subsequently, 118.5g potassium permanganate was slowly divided into multiple batches, the system was reacted at reflux temperature for 24h, manganese dioxide was filtered while hot, the filtrate was washed with hot water, concentrated, acidified with 2M hydrochloric acid solution, filtered and dried to obtain compound A1 31.3 g, yield 72%. Step 2: Synthesis of Intermediate Compound A2

[0075] 29.0g of 6-nitro-3-bromophthalic acid, 27.94g of pinacol biboronate, 49.1g of potassium acetate and 300mL of DMSO were sequentially added to the four-necked flask, and magnetic stirring was turned on. 7.3 g of 1,1'-bis(diphenylphosphino)ferrocene]dichloride palladium (Pd(dppf)Cl were subse...

Synthetic example 2

[0081] A diamine compound C-2, the structure is as follows:

[0082]

[0083] The difference between the preparation method and Synthesis Example 1 is that the compound 6-nitro-3-bromo-o-xylene in step (1) is used 6-nitro-4-bromo-o-xylene. Replacement; the target product C-2 was finally obtained, the yield was 3.55 g, and the yield was 21.5%.

[0084] The structural test data of the target product C-2 are as follows:

[0085] 1 H-NMR (400MHz, DMSO-d6), δ(ppm): 13.1(2H,s), 12.8(2H,s), 8.6(2H,d), 7.8(2H,d), 7.6(4H,s) , 5.9 (4H, s); elemental analysis (%): C (59.48), H (4.25), N (6.16).

Synthetic example 3

[0087] A diamine compound C-3, the structure is as follows:

[0088]

[0089] The difference between preparation method and synthesis example 1 is that the 6-nitro-3-bromo-o-xylene in step (1) is used 6-nitro-4-bromo-o-xylene. Replace the compound p-dibromobenzene in step (3) with 4,4'-dibromobiphenyl Substitution; the target product C-3 was finally obtained, 4.83 g, and the yield was 25.2%.

[0090] The structural test data of the target product C-3 are as follows:

[0091] 1 H-NMR (400MHz, DMSO-d6), δ(ppm): 13.1(2H,s), 12.8(2H,s), 8.6(2H,d), 7.8(2H,d), 7.6(8H,s) , 5.9 (4H, s); elemental analysis (%): C (64.85), H (4.05), N (5.35).

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Abstract

The present invention provides a polyimide precursor composition, a preparation method and application thereof, wherein the polyimide precursor composition is obtained by polycondensation of aromatic tetracarboxylic dianhydride and diamine monomers; The amine monomers include at least one diamine compound having the structure shown in formula I. The diamine compound contains an ortho-dicarboxyl structural group, which can cause a cross-linking reaction between free molecular chains during the curing process of the polyimide precursor, improve the stability and molecular weight of the molecular structure, and ensure the flexible substrate material. heat resistance, dimensional stability and mechanical properties. The polyimide film obtained by curing the polyimide precursor composition has high glass transition temperature and thermal decomposition temperature, low thermal expansion coefficient, high tensile strength, excellent thermal stability and dimensional stability. It can fully meet the process requirements and subsequent use requirements of flexible display devices.

Description

technical field [0001] The invention belongs to the technical field of flexible materials, and in particular relates to a polyimide precursor composition and a preparation method and application thereof. Background technique [0002] With the rapid development of smart display terminals in the direction of thinness, high definition, bendability, curling and folding, flexible display has gradually become an important mainstream display technology for smart display terminals, which is widely used in smart phones, wearable devices, Display fields such as large-size TVs. In flexible display devices, flexible substrates are the key materials to realize flexible displays. Flexible substrates are used to replace traditional rigid glass substrates to realize display forms such as bending, folding and curling of display terminals. Among various flexible display substrate materials, polyimide has become an important display substrate material due to its good heat resistance, low coef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/10G09F9/30
CPCC08G73/1042C08G73/1067C08G73/1085C08G73/1071C08G73/1039G09F9/301Y02E10/549
Inventor 吴京玮王雪岚李琳
Owner FUYANG XINYIHUA MATERIAL TECH
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