CN114380997A - Preparation method of high-temperature-resistant polyimide film with low thermal expansion coefficient - Google Patents
Preparation method of high-temperature-resistant polyimide film with low thermal expansion coefficient Download PDFInfo
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- CN114380997A CN114380997A CN202111545900.0A CN202111545900A CN114380997A CN 114380997 A CN114380997 A CN 114380997A CN 202111545900 A CN202111545900 A CN 202111545900A CN 114380997 A CN114380997 A CN 114380997A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Abstract
The invention relates to a preparation method of a high-temperature resistant polyimide film with a low thermal expansion coefficient, which comprises the following steps: 1) carrying out amidation reaction on a diamine monomer and a dianhydride monomer in an aprotic solvent to obtain a polyamic acid solution; 2) defoaming the obtained polyamic acid solution, and preparing a uniform liquid film by a coating or curtain coating method; 3) and (3) performing gradient temperature rise to perform thermal imidization reaction, and forming a film to obtain the polyimide film. The advantages are that: the diamine and the dianhydride in the biphenyl structure are selected, so that the linear chain degree of a molecular chain can be effectively improved, and the thermal expansion coefficient of the polymer is reduced. Methyl and trifluoromethyl functional groups are added, so that the steric hindrance is increased, the distance between chains is increased, the thermal expansion coefficient of the polymer is further reduced, and the linear thermal expansion coefficient is 2-35 ppm/K.
Description
Technical Field
The invention belongs to the field of preparation and application of polyimide, and particularly relates to a preparation method of a high-temperature-resistant polyimide film with a low thermal expansion coefficient.
Background
In the industries of photoelectric display and the like, a polyimide film is generally used for replacing a glass material, so that the characteristics of lightness, thinness, folding and the like of a screen can be realized. Polyimide films are often used in combination with inorganic materials that are subjected to high heat environments during processing. In addition, when an electronic component including an inorganic material is combined with an organic thin film, the thin film device formed is likely to be peeled or separated during processing or bending due to the significant difference in thermal expansion coefficient between the inorganic material and the organic thin film. Therefore, the polyimide material is required to have high heat resistance and high dimensional stability, but the conventional polyimide material at present is difficult to meet the requirements of high heat resistance, low thermal expansion and the like.
The presently disclosed PI with the lowest coefficient of thermal expansion is prepared by a biaxially oriented film process. There are also patents disclosing solutions to reduce the coefficient of thermal expansion by adjusting the linear structure or the ratio of the polymer by changing the monomer structure of the dianhydride or diamine, such as CN105175723A, CN 110156991A; furthermore, the thermal expansion coefficient of polyimide films can also be reduced by adding inorganic nanoparticles, such as silica, to the polyimide system, for example patent No. cn201380034887. x. However, the flexible substrate has severe requirements for the film during processing, and the film is required to have extremely small surface roughness, good heat resistance (>350 ℃) and excellent mechanical properties, and especially low thermal expansion coefficient is important for the application of polyimide film.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a preparation method of a high-temperature-resistant polyimide film with a low thermal expansion coefficient, wherein the glass transition temperature of the polyimide film reaches more than 350 ℃ and the linear thermal expansion coefficient is 2-35 ppm/K by adding functional groups such as methyl, trifluoromethyl and the like.
In order to achieve the purpose, the invention is realized by the following technical scheme:
a preparation method of a high-temperature resistant polyimide film with a low thermal expansion coefficient comprises the following steps:
1) carrying out amidation reaction on a diamine monomer and a dianhydride monomer in an aprotic solvent to obtain a polyamic acid solution;
2) defoaming the obtained polyamic acid solution, and preparing a uniform liquid film by a coating or curtain coating method;
3) and (3) performing gradient temperature rise to perform thermal imidization reaction, and forming a film to obtain the polyimide film.
The gradient temperature rise comprises the following steps: heating the liquid film to 60-400 ℃ at a heating rate of 1-10 ℃/min, and heating for 2-10 h.
The gradient temperature rise comprises the following steps: heating the liquid film to 120-140 ℃ at a heating rate of 1-10 ℃/min, preserving heat for 0.5-1 h, heating to 160-180 ℃ at a heating rate of 1-10 ℃/min, preserving heat for 0.5-1 h, heating to 250-270 ℃ at a heating rate of 1-10 ℃/min, preserving heat for 0.5-1 h, heating to 330-350 ℃ at a heating rate of 1-10 ℃/min, and preserving heat for 0.5-1 h. The ratio of the diamine monomer to the dianhydride monomer is 1: 0.5-1: 2.
The dianhydride monomer is more than one of the following compounds:
the diamine monomer is more than one of the following compounds:
the non-protonized solvent is DMAC and DMF.
Compared with the prior art, the invention has the beneficial effects that:
according to the method, the diamine and the dianhydride in the biphenyl structure are selected, so that the linear chain degree of a molecular chain can be effectively improved, and the thermal expansion coefficient of the polymer is reduced. The methyl and trifluoromethyl functional groups are added, so that the steric hindrance is increased, the distance between chains is increased, the thermal expansion coefficient of the polymer is further reduced, the glass transition temperature of the polyimide film is more than 350 ℃, and the linear thermal expansion coefficient is 2-35 ppm/K.
Detailed Description
The present invention is described in detail below, but it should be noted that the practice of the present invention is not limited to the following embodiments.
A preparation method of a high-temperature resistant polyimide film with a low thermal expansion coefficient comprises the following steps:
1) carrying out amidation reaction on a diamine monomer and a dianhydride monomer in an aprotic solvent to obtain a polyamic acid solution;
wherein the amount ratio of the diamine monomer to the dianhydride monomer is 1: 0.5-1: 2;
the dianhydride monomer is more than one of the following three compounds:
the diamine monomer is more than one of the following five compounds:
2) defoaming the obtained polyamic acid solution, and preparing a uniform liquid film by a coating or curtain coating method;
3) and (3) performing gradient temperature rise to perform thermal imidization reaction, and forming a film to obtain the polyimide film.
The gradient temperature rise is as follows: heating the liquid film to 60-400 ℃ at a heating rate of 1-10 ℃/min for 2-10 h. Specifically, the temperature is increased to 120-140 ℃ at the temperature increase rate of 1-10 ℃/min and is kept for 0.5-1 h, then the temperature is increased to 160-180 ℃ at the same temperature increase rate and is kept for 0.5-1 h, then the temperature is increased to 250-270 ℃ at the same temperature increase rate and is kept for 0.5-1 h, and then the temperature is increased to 330-350 ℃ at the same temperature increase rate and is kept for 0.5-1 h.
[ example 1 ]
P-phenylenediamine C is added into a 100ml three-neck flask6H8N22.1628g (0.020mol), 25g N, N-dimethylacetamide was added to dissolve the diamine, and 4,4' - (hexafluoroisopropylidene) diphthalic anhydride C was added thereto19H6F6O6)8.8848g (0.020mol), 20.9639g of N, N-dimethylacetamide C was added4H9NO, stirring and reacting for 24h at room temperature to obtain polyamic acid (PAA) solution.
Coating a polyamic acid solution to obtain a polyamic acid film, heating at a heating rate of 2-8 ℃/min, preserving heat at 120-140 ℃ for 0.5min, heating to 160-180 ℃ at the same heating rate, preserving heat for 0.5min, heating to 250-270 ℃ for 0.5min, heating to 330-350 ℃ for 0.5min, and performing gradient imidization to obtain the high-temperature-resistant polyimide film with a low thermal expansion coefficient. The CTE was measured to be 35 ppm/K.
[ example 2 ]
2- (4-aminophenyl) -5-ammonia was added to a 100ml three-necked flaskPhenylbenzimidazoles (C)13H12N4)4.4854g (0.020mol), 25g N, N-dimethylacetamide was added to dissolve the diamine, and 4,4' - (hexafluoroisopropylene) diphthalic anhydride (C) was added thereto19H6F6O6)8.8848g (0.020mol), 28.4808g of N, N-dimethylacetamide was added, and the mixture was stirred at room temperature for 24 hours to obtain a polyamic acid (PAA) solution.
Coating the polyamic acid solution to obtain a polyamic acid film, heating at a heating rate of 2-8 ℃/min, preserving heat at 120-140 ℃ for 0.5min, heating to 160-180 ℃ for 0.5min, heating to 250-270 ℃ for 0.5min, heating to 330-350 ℃ for 0.5min, and performing gradient imidization to obtain the high-temperature-resistant polyimide film with a low thermal expansion coefficient. The CTE was measured to be 10 ppm/K.
[ example 3 ]
4,4 '-diamino-2, 2' -bistrifluoromethylbiphenyl (C) was added to a 100ml three-necked flask16H10F6N2)6.4048g (0.020mol), 25g N, N-dimethylacetamide was added to dissolve the diamine, and 4,4' - (hexafluoroisopropylene) diphthalic anhydride (C) was added thereto19H6F6O6)8.8848g (0.020mol), 36.1584g of N, N-dimethylacetamide was added, and the mixture was stirred at room temperature for 24 hours to obtain a polyamic acid (PAA) solution.
Coating the polyamic acid solution to obtain a polyamic acid film, heating at a heating rate of 3-10 ℃/min, preserving heat at 120-140 ℃ for 0.5min, heating to 160-180 ℃ for 0.5min, heating to 250-270 ℃ for 0.5min, heating to 330-350 ℃ for 0.5min, and performing gradient imidization to obtain the high-temperature-resistant polyimide film with a low thermal expansion coefficient. The CTE was measured to be 24 ppm/K.
[ example 4 ]
2.1628g (0.020mol) of p-phenylenediamine was put into a 100ml three-necked flask, 25g (25 g N g) of N-dimethylacetamide was added to dissolve the diamine, 5.8844g (0.020mol) of biphenyltetracarboxylic dianhydride was added thereto, 28.8543g of N, N-dimethylacetamide was added thereto, and the mixture was stirred at room temperature for 24 hours to react to obtain a polyamic acid (PAA) solution.
Coating the polyamic acid solution to obtain a polyamic acid film, heating at a heating rate of 1-7 ℃/min, preserving heat at 120-140 ℃ for 0.5min, heating to 160-180 ℃ for 0.5min, heating to 250-270 ℃ for 0.5min, heating to 330-350 ℃ for 0.5min, and performing gradient imidization to obtain the high-temperature-resistant polyimide film with a low thermal expansion coefficient.
[ example 5 ]
4,4 '-diamino-2, 2' -bistrifluoromethylbiphenyl (C) was added to a 100ml three-necked flask16H10F6N2)6.4048g (0.020mol), 25g N, N-dimethylacetamide was added to dissolve the diamine, and biphenyltetracarboxylic dianhydride (C) was added thereto16H6O6)5.8844g (0.020mol), 57.2431g of N, N-dimethylacetamide was added, and the mixture was stirred at room temperature for 24 hours to obtain a polyamic acid (PAA) solution.
Coating the polyamic acid solution to obtain a polyamic acid film, heating at a heating rate of 3-9 ℃/min, preserving heat at 120-140 ℃ for 0.5min, heating to 160-180 ℃ for 0.5min, heating to 250-270 ℃ for 0.5min, heating to 330-350 ℃ for 0.5min, and performing gradient imidization to obtain the high-temperature-resistant polyimide film with a low thermal expansion coefficient. The CTE was measured to be 15 ppm/K.
[ example 6 ]
4,4' -diamino-2, 2' -dimethyl-1, 1' -biphenyl (C) was added to a 100ml three-necked flask14H16N2)4.2460g (0.020mol), 25g N, N-dimethylacetamide was added to dissolve the diamine, and biphenyltetracarboxylic dianhydride (C) was added thereto16H6O6)5.8844g (0.020mol), 15.5216g of N, N-dimethylacetamide was added, and the mixture was stirred at room temperature for 24 hours to obtain a polyamic acid (PAA) solution.
Coating the polyamic acid solution to obtain a polyamic acid film, heating at a heating rate of 1-10 ℃/min, preserving heat at 120-140 ℃ for 0.5min, heating to 160-180 ℃ for 0.5min, heating to 250-270 ℃ for 0.5min, heating to 330-350 ℃ for 0.5min, and performing gradient imidization to obtain the high-temperature-resistant polyimide film with a low thermal expansion coefficient. The CTE was measured to be 9.8 ppm/K.
Claims (7)
1. A preparation method of a high-temperature resistant polyimide film with a low thermal expansion coefficient is characterized by comprising the following steps:
1) carrying out amidation reaction on a diamine monomer and a dianhydride monomer in an aprotic solvent to obtain a polyamic acid solution;
2) defoaming the obtained polyamic acid solution, and preparing a uniform liquid film by a coating or curtain coating method;
3) and (3) performing gradient temperature rise to perform thermal imidization reaction, and forming a film to obtain the polyimide film.
2. The method for preparing the high temperature resistant polyimide film with low thermal expansion coefficient according to claim 1, wherein the gradient temperature rise is as follows: heating the liquid film to 60-400 ℃ at a heating rate of 1-10 ℃/min, and heating for 2-10 h.
3. The method for preparing the high temperature resistant polyimide film with low thermal expansion coefficient according to claim 1, wherein the gradient temperature rise is as follows: heating the liquid film to 120-140 ℃ at a heating rate of 1-10 ℃/min, preserving heat for 0.5-1 h, heating to 160-180 ℃ at a heating rate of 1-10 ℃/min, preserving heat for 0.5-1 h, heating to 250-270 ℃ at a heating rate of 1-10 ℃/min, preserving heat for 0.5-1 h, heating to 330-350 ℃ at a heating rate of 1-10 ℃/min, and preserving heat for 0.5-1 h.
4. The method of claim 1, wherein the diamine monomer and the dianhydride monomer are added in a ratio of 1:0.5 to 1: 2.
5. The method for preparing the high temperature resistant polyimide film with low thermal expansion coefficient according to claim 1, wherein the dianhydride monomer is one or more of the following compounds:
6. the method for preparing a high temperature resistant polyimide film with low thermal expansion coefficient as claimed in claim 1, wherein the diamine monomer is one or more of the following compounds:
7. the method for preparing a high temperature resistant polyimide film with low thermal expansion coefficient as claimed in claim 1, wherein the non-protonized solvent is DMAC or DMF.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101259544B1 (en) * | 2011-06-29 | 2013-04-30 | 웅진케미칼 주식회사 | Polyimide film |
| CN106928481A (en) * | 2017-04-06 | 2017-07-07 | 上海交通大学 | The optimization preparation method of Kapton |
| KR20170092939A (en) * | 2016-02-04 | 2017-08-14 | 주식회사 효성 | A PolyImide film having a low coefficient of thermal expansion and preparation method thereof |
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| CN109053582A (en) * | 2018-06-26 | 2018-12-21 | 同济大学 | Diamine monomer, heat-proof polyimide containing aromatic rings and glyoxaline structure and preparation method thereof |
| CN110330645A (en) * | 2019-06-20 | 2019-10-15 | 重庆文理学院 | One kind soluble polyimide containing benzimidazole structure and preparation method thereof |
| CN111704735A (en) * | 2020-06-24 | 2020-09-25 | 中国科学院光电技术研究所 | Ultralow-thermal-expansion-coefficient high-strength polyimide optical film material and preparation method thereof |
| CN112831071A (en) * | 2020-12-31 | 2021-05-25 | 武汉柔显科技股份有限公司 | Method for preparing polyimide film from polyamide acid slurry |
-
2021
- 2021-12-16 CN CN202111545900.0A patent/CN114380997A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101259544B1 (en) * | 2011-06-29 | 2013-04-30 | 웅진케미칼 주식회사 | Polyimide film |
| KR20170092939A (en) * | 2016-02-04 | 2017-08-14 | 주식회사 효성 | A PolyImide film having a low coefficient of thermal expansion and preparation method thereof |
| CN106928481A (en) * | 2017-04-06 | 2017-07-07 | 上海交通大学 | The optimization preparation method of Kapton |
| CN109053582A (en) * | 2018-06-26 | 2018-12-21 | 同济大学 | Diamine monomer, heat-proof polyimide containing aromatic rings and glyoxaline structure and preparation method thereof |
| CN109021265A (en) * | 2018-07-02 | 2018-12-18 | 溧阳华晶合成材料有限公司 | A method of preparing the polyimide film of high-modulus low thermal coefficient of expansion |
| CN110330645A (en) * | 2019-06-20 | 2019-10-15 | 重庆文理学院 | One kind soluble polyimide containing benzimidazole structure and preparation method thereof |
| CN111704735A (en) * | 2020-06-24 | 2020-09-25 | 中国科学院光电技术研究所 | Ultralow-thermal-expansion-coefficient high-strength polyimide optical film material and preparation method thereof |
| CN112831071A (en) * | 2020-12-31 | 2021-05-25 | 武汉柔显科技股份有限公司 | Method for preparing polyimide film from polyamide acid slurry |
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