CN112409311A - Dianhydride, polyimide film and application thereof - Google Patents
Dianhydride, polyimide film and application thereof Download PDFInfo
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- CN112409311A CN112409311A CN202011168595.3A CN202011168595A CN112409311A CN 112409311 A CN112409311 A CN 112409311A CN 202011168595 A CN202011168595 A CN 202011168595A CN 112409311 A CN112409311 A CN 112409311A
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
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- 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
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Abstract
The invention provides dianhydride with a brand new structure, which contains trifluoromethyl, alicyclic structure, amido or ester group, can be polymerized with diamine to obtain polyimide with excellent performances of high heat resistance, low thermal expansion, high light transmission and the like, and can be used for color filters, image display devices and various electronic devices.
Description
Technical Field
The invention relates to the technical field of materials, in particular to dianhydride, polyimide and a polyimide film, and also relates to application of the polyimide and the polyimide film in color filters, image display devices and electronic devices.
Background
In recent years, polyimide has been widely used in the market because of its excellent properties. Particularly in the fields of photoelectricity, electronics and the like, with the development of flexible displays, flexible organic electroluminescent devices, flexible solar cells and the like, related electronic and optical devices face new requirements for miniaturization, high integration, flexibility and the like. To cope with these trends, various polyimide materials having different properties have been developed.
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. This requires that the polyimide material have high heat resistance and a linear expansion coefficient matching that of the inorganic material. Recently, polyimide materials have begun to replace inorganic glass as cover plate materials of AMOLED screens, and the polyimide materials are required to be highly transparent when used on mobile phones. At present, the traditional polyimide material is difficult to meet the requirements of high heat resistance, low expansion, transparency and the like.
The invention patent CN108659533A obtains a polyimide film with good heat resistance and low thermal expansion by synthesizing a macromolecule with amide groups (or ester groups) and linear rigid groups in the repeating units of the molecular chains, but the application of the material is limited because of low transparency.
Disclosure of Invention
Based on the technical problems in the prior art, the invention provides dianhydride, polyimide and a polyimide film, wherein the polyimide film has excellent performances of high heat resistance, low thermal expansion and high light transmittance.
The technical scheme of the invention is as follows:
the invention provides dianhydride, which has the following structural formula:
wherein Z is NH or O.
Preferably, the dianhydride is of the formula:
the invention also provides polyimide which is obtained by polymerizing the dianhydride monomer and the diamine monomer.
Preferably, the diamine monomer is selected from one or two of the following diamines: 2,2' -bis (trifluoromethyl) diaminobiphenyl, p-phenylenediamine, 4' -diaminobiphenyl, 2, 6-diaminonaphthalene, 4' -diaminodiphenyl ether, 3,4' -diaminodiphenyl ether, m-phenylenediamine, N ' -bis (4-aminophenyl) terephthalamide, 4' -diaminobenzanilide, 4' -diaminodiphenylmethane, 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene, 1, 4-diaminocyclohexane.
More preferably, the diamine monomer is 2,2 '-bis (trifluoromethyl) diaminobiphenyl, p-phenylenediamine, 4' -diaminobiphenyl.
The invention also provides a polyimide film prepared from the polyimide.
The invention also provides application of the polyimide or the polyimide film in preparing color filters, image display devices and electronic devices.
The invention provides dianhydride with a brand-new structure through molecular structure design, which contains trifluoromethyl, alicyclic structure, amido or ester group, so that polyimide obtained by polymerizing the dianhydride and diamine has excellent performances of high heat resistance, low thermal expansion, high light transmittance and the like, and can be used for color filters, image display devices and various electronic devices.
Detailed Description
The invention provides dianhydride with a brand new structure, which has the structural formula as follows:
wherein Z is NH or O.
Preferably, the dianhydride has the formula:
the invention also provides polyimide which is obtained by polymerizing the dianhydride monomer and the diamine monomer.
The inventors have introduced trifluoromethyl, alicyclic structure, amide group or ester group at a specific position in the dianhydride structure of formula (1) to suppress charge transfer between or within molecules of polyimide obtained from the dianhydride and improve transparency while maintaining the original excellent properties of polyimide such as heat resistance; and the polyimide molecules have better linear regularity.
The dianhydride structure of formula (2) preferably contains an amide bond, and the resulting polyimide has a low coefficient of linear thermal expansion because the molecules are not only linear but also have a strong intermolecular force.
In the present invention, the synthesis of the dianhydride represented by formula (1) is not limited, and can be obtained by a conventionally known synthesis method, for example, by the following synthesis method:
the polyimide provided by the invention is obtained by polymerizing the dianhydride monomer and the diamine monomer. The diamine monomers include, but are not limited to, the following monomers:
2,2' -bis (trifluoromethyl) diaminobiphenyl, p-phenylenediamine, 4' -diaminobiphenyl, 2, 6-diaminonaphthalene, 4' -diaminodiphenyl ether, 3,4' -diaminodiphenyl ether, m-phenylenediamine, N ' -bis (4-aminophenyl) terephthalamide, 4' -diaminobenzanilide, 4' -diaminodiphenylmethane, 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene, 1, 4-diaminocyclohexane, and the like.
When the polyimide is obtained by polymerization with the dianhydride, one or two diamine monomers may be selected and used.
The method for producing the polyimide of the present invention is not particularly limited, and a polyimide precursor, polyamic acid, can be obtained by a known "one-step" or "two-step" method, and then imidized by a thermal imidization method or a chemical imidization method to obtain the polyimide. Chemical imidization is preferred in the present invention.
The chemical imidization method involves adding a chemical imidizing agent containing an organic acid anhydride and a tertiary amine as a catalyst dropwise to a polyimide precursor varnish obtained by polymerization or a polyimide precursor varnish diluted with a solvent while stirring, and allowing the mixture to react sufficiently to complete imidization.
The organic acid anhydride used for the chemical imidization is not particularly limited, and acid anhydride reagents which facilitate the reaction, such as acetic anhydride, propionic anhydride, maleic anhydride, and phthalic anhydride, are generally used. In view of the above, acetic anhydride is preferred. The tertiary amine is also not particularly limited, and pyridine, triethylamine and the like can be used, but pyridine is preferred from the viewpoint of safety.
The amount of the organic acid anhydride in the chemical imidization is not particularly limited, but is preferably 1 to 10 times, preferably 2 to 5 times, the molar amount of the theoretical shrinkage of the polyimide precursor. The amount of the tertiary amine to be used is not particularly limited, but is preferably 0.1 to 1 times by mole relative to the amount of the organic acid anhydride.
After imidization is completed by a chemical imidization method, polyimide is precipitated after a large amount of a poor solvent is added to the reaction solution. The solvent, the chemical imidizing agent, the catalyst, and the like can be removed by repeated washing, and then, the powder of the polyimide can be obtained by drying under reduced pressure. The poor solvent to be used is not particularly limited as long as it does not dissolve the polyimide, and water, methanol, ethanol, n-propanol, isopropanol, and the like, and a mixed solvent thereof are usually preferably used. The amount of the poor solvent is preferably equal to or more than the amount of the polyimide solution, and more preferably 2 to 3 times the amount of the polyimide solution. The polyimide cleaning solvent is also preferably a poor solvent.
The polyimide cleaned by the above-mentioned method may be vacuum drying or hot air drying. Vacuum drying is preferred for complete drying of the solvent in the resin. The drying temperature is preferably in the range of 80 to 200 ℃ and the drying time is not limited, but is preferably 8 hours or more from the viewpoint of cost and drying effect.
There are many methods for forming a polyimide film, and the polyimide film can be produced by coating a polyimide solution on a support and drying the polyimide solution, or a polyimide film can be obtained by coating a polyamic acid on a support, heating the obtained film to complete imidization, and sufficiently drying the film. In order to obtain more excellent thermal expansion characteristics and dimensional stability, the present invention preferably uses a method of dissolving polyimide in an organic solvent, applying the solution to a substrate, and drying the solution.
The organic solvent used herein is not particularly limited, and commonly used are amide solvents, ketone solvents, ether solvents, ester solvents, and the like; the above-mentioned at least 1 kind of organic solvent is preferably selected, and more preferably an amide-based solvent, a ketone-based solvent, an ether-based solvent or a mixed solution thereof, and the above-mentioned preferred agents can prevent whitening, non-leveling, curing or the like from occurring due to moisture absorption of the coating film during coating and drying.
Among them, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like are particularly preferable as the amide solvent. Particularly preferred ketone solvents include methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone. Particularly preferred ether solvents include monoethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether.
Hereinafter, the technical solution of the present invention will be described in detail by specific examples, but these examples should be explicitly proposed for illustration, but should not be construed as limiting the scope of the present invention.
Example 1
Synthesis of dianhydride
7.9268g (40mmol) of hydrogenated trimellitic anhydride is dissolved in 50mL of pyridine solution in an ice-water bath, excessive thionyl chloride is added after the dissolution, the reflux reaction is carried out for 10 hours at 75 ℃, the reaction solution becomes yellow clear liquid after the reaction, the excessive thionyl chloride is removed under normal pressure, and the yellow clear liquid becomes yellow viscous liquid. Extracting, recrystallizing and vacuum drying for 12h to obtain the hydrogenated trimellitic anhydride chloride. The obtained hydrogenated trimellitic anhydride acid chloride was dissolved in 12.5mL of tetrahydrofuran under ice, 6.4046g (20mmol) of 2,2' -bis (trifluoromethyl) diaminobiphenyl (TFMB), 3.50mL of THF and 6.6mL (80mmol) of pyridine solution were added by syringe, sufficiently stirred until the reaction was completed, allowed to stand for 12 hours, the obtained precipitate was filtered, sufficiently washed with THF, and the obtained powder was subjected to distillation under reduced pressure at 100 ℃ for 8 hours to obtain dianhydride, with a yield of 90.2%, of the formula:
the dianhydride was characterized by infrared ray and was confirmed to be 1324cm-1Has a C-N stretching vibration peak on amide, a C ═ O stretching vibration peak on amide at 1779cm-1, and a C ═ O stretching vibration peak at 3305cm-1At the NH stretching vibration peak on amido bond, 1760, 1790cm-1The stretching vibration peak of the carbonyl of the acid anhydride is shown.
Synthesis of polyimide
3.2023g (10mmol) of TFMB was dissolved in 40mL of N, N-dimethylacetamide, 6.8056(10mmol) of dianhydride was added slowly, and the reaction was stirred at room temperature for 8 hours. Adding 2.38g of pyridine as a catalyst and 3.06g of acetic anhydride as a dehydrating agent into the polyamic acid solution, stirring at 25 ℃ for 30 minutes, stirring at 70 ℃ for 1 hour, cooling to room temperature, transferring the reaction solution into a dropping funnel, dropwise adding the solution into a beaker filled with 1.5L of methanol at a speed of 2-3 drops/second to gradually precipitate, washing the precipitate with a large amount of methanol, filtering and crushing the solid precipitate, and vacuum-drying at 100 ℃ to obtain polyimide powder.
Polyimide film
Dissolving polyimide powder obtained by using N-methyl pyrrolidone completely to obtain a solution with the solid content of 10%, coating the obtained solution on a glass substrate, placing the glass plate in a drying oven at 80 ℃ for 0.5h, heating to 150 ℃, drying for 1h, taking out the glass plate after the temperature is reduced to 25 ℃, placing the glass plate in water for demoulding, and then placing the film in a drying oven at 100 ℃ for drying and removing water to obtain the polyimide film.
Example 2
Synthesis of dianhydride As in example 1
The procedure of example 1 was repeated, except that 1.0814g (10mmol) of p-phenylenediamine was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 3
Synthesis of dianhydride As in example 1
The procedure of example 1 was repeated, except that 1.8424g (10mmol) of 4,4' -diaminobiphenyl was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 4
Synthesis of dianhydride As in example 1
The procedure of example 1 was repeated, except that 1.5807g (10mmol) of 2, 6-diaminonaphthalene was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 5
Synthesis of dianhydride As in example 1
The procedure of example 1 was repeated, except that 2.0024g (10mmol) of 4,4' -diaminodiphenyl ether was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 6
Synthesis of dianhydride As in example 1
The procedure of example 1 was repeated, except that 2.0024g (10mmol) of 3,4' -diaminodiphenyl ether was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 7
Synthesis of dianhydride As in example 1
The procedure of example 1 was repeated, except that 1.0814g (10mmol) of m-phenylenediamine was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 8
Synthesis of dianhydride As in example 1
Synthesis of polyimide
Example 1 was repeated except that 3.4639g (10mmol) of N, N' -bis (4-aminophenyl) terephthalamide was dissolved in 40mLN, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mLN, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 9
Synthesis of dianhydride As in example 1
Synthesis of polyimide
Example 1 was repeated except that 2.2727g (10mmol) of 4,4' -diaminobenzanilide was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 10
Synthesis of dianhydride As in example 1
Synthesis of polyimide
The procedure of example 1 was repeated, except that 1.9827g (10mmol) of 4,4' -diaminodiphenylmethane was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 11
Synthesis of dianhydride As in example 1
Synthesis of polyimide
Example 1 was followed except that 4.2833g (10mmol) of 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Example 12
Synthesis of dianhydride As in example 1
Synthesis of polyimide
Example 1 was repeated except that 1.1419g (10mmol) of 1, 4-diaminocyclohexane was dissolved in 40mL of N, N-dimethylacetamide instead of 3.2023g (10mmol) of TFMB in 40mL of N, N-dimethylacetamide in the synthesis of polyimide. The polyimide film was prepared as in example 1.
Comparative example 1
Polyimide was synthesized as in example 1 except that 4.4424g (10mmol) of hexafluorodianhydride was used in place of the dianhydride of example 1. The polyimide film was prepared as in example 1.
Comparative example 2
Polyimide was synthesized in the same manner as in example 1 except that 2.1812g (10mmol) of pyromellitic dianhydride was used in place of the dianhydride in example 1. The polyimide film was prepared as in example 1.
Comparative example 3
The inventor synthesizes diamine with a brand new structure in the prophase, wherein the structure contains trifluoromethyl, acylamino or ester group, and the specific structure is as follows
The diamine can be obtained by adopting a conventional diamine synthesis method, and the diamine and 1,2,4, 5-cyclohexane tetracarboxylic dianhydride are polymerized to obtain polyimide. The polyimide film was prepared in the same manner as in example 1.
The infrared characterization of the polyimide film shows that the polyimide film has peaks at 1365cm-1 (C-N stretching vibration peak on imide), 1692cm-1 (C ═ O asymmetric stretching peak on imide), 1776cm-1 (C ═ O symmetric stretching peak on imide) and 3298cm-1 (NH-vibration peak on amido bond).
Test example:
the polyimide films obtained in examples 1 to 12 and comparative examples 1 to 3 were subjected to a performance test in the following manner, and the results are shown in Table 1.
Coefficient of linear thermal expansion: a thermal mechanical analyzer was used to apply a 50mN load under a nitrogen atmosphere, and the temperature was measured at a temperature rise rate of 10 ℃/min to obtain an average value.
Glass transition temperature: DSC measurement was performed at a temperature rise rate of 10 ℃/min under a nitrogen atmosphere using a differential scanning calorimeter, and the glass transition temperature was determined.
Total light transmittance: the total light transmittance was measured by uv-vis spectroscopy.
Light transmittance at wavelength 400 nm: the transmittance was measured at 400nm using an ultraviolet spectrophotometer.
TABLE 1 test results of polyimide films obtained in examples and comparative examples
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (7)
1. A dianhydride is characterized by having a structural formula shown as follows:
wherein Z is NH or O.
2. The dianhydride according to claim 1, characterized by the following structural formula:
3. a polyimide obtained by polymerizing the dianhydride monomer according to claim 1 or 2 with a diamine monomer.
4. The polyimide according to claim 3, wherein the diamine monomer is selected from one or two of the following diamines: 2,2' -bis (trifluoromethyl) diaminobiphenyl, p-phenylenediamine, 4' -diaminobiphenyl, 2, 6-diaminonaphthalene, 4' -diaminodiphenyl ether, 3,4' -diaminodiphenyl ether, m-phenylenediamine, N ' -bis (4-aminophenyl) terephthalamide, 4' -diaminobenzanilide, 4' -diaminodiphenylmethane, 1, 4-bis (4-amino-2-trifluoromethylphenoxy) benzene, 1, 4-diaminocyclohexane.
5. The polyimide according to claim 3 or 4, wherein the diamine monomer is 2,2 '-bis (trifluoromethyl) diaminobiphenyl, p-phenylenediamine, 4' -diaminobiphenyl.
6. A polyimide film obtained from the polyimide according to claim 3 or 4.
7. Use of the polyimide according to any one of claims 3 to 5 or the polyimide film according to claim 6 for producing a color filter, an image display device, and an electronic device.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024807A (en) * | 2021-03-15 | 2021-06-25 | 吉林奥来德光电材料股份有限公司 | Deuterated fluorine-containing polyimide, polyimide precursor, polyimide film, preparation method and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012072121A (en) * | 2010-09-01 | 2012-04-12 | Nippon Fine Chem Co Ltd | Amide group-bearing alicyclic tetracarboxylic dianhydride, and resin obtained by using the same |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012072121A (en) * | 2010-09-01 | 2012-04-12 | Nippon Fine Chem Co Ltd | Amide group-bearing alicyclic tetracarboxylic dianhydride, and resin obtained by using the same |
| JP2012072118A (en) * | 2010-09-01 | 2012-04-12 | Nippon Fine Chem Co Ltd | Amide group-bearing alicyclic tetracarboxylic dianhydride, and resin obtained by using the same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024807A (en) * | 2021-03-15 | 2021-06-25 | 吉林奥来德光电材料股份有限公司 | Deuterated fluorine-containing polyimide, polyimide precursor, polyimide film, preparation method and application |
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