CN111647270A - Insulating polyimide film and preparation method thereof - Google Patents
Insulating polyimide film and preparation method thereof Download PDFInfo
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- CN111647270A CN111647270A CN202010472518.0A CN202010472518A CN111647270A CN 111647270 A CN111647270 A CN 111647270A CN 202010472518 A CN202010472518 A CN 202010472518A CN 111647270 A CN111647270 A CN 111647270A
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- polyimide film
- dianhydride
- monomer
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- diamine
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 56
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000004985 diamines Chemical class 0.000 claims abstract description 38
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 22
- 239000011737 fluorine Substances 0.000 claims abstract description 22
- AUPIFOPXTAGGSW-UHFFFAOYSA-N 4-[4-[9-[4-(4-aminophenoxy)phenyl]fluoren-9-yl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 AUPIFOPXTAGGSW-UHFFFAOYSA-N 0.000 claims abstract description 12
- ADLOLHYLFUJLHJ-UHFFFAOYSA-N aminosilyloxyperoxybenzene Chemical compound N[SiH2]OOOC1=CC=CC=C1 ADLOLHYLFUJLHJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 15
- SXFKVWHNCURLRL-UHFFFAOYSA-N N[SiH](OC1=CC=CC=C1)O[SiH2]O Chemical compound N[SiH](OC1=CC=CC=C1)O[SiH2]O SXFKVWHNCURLRL-UHFFFAOYSA-N 0.000 claims description 10
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical group C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 claims description 6
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical group C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
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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
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- 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
-
- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- 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
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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 discloses an insulating polyimide film, which comprises the following raw materials: diamine monomer, dianhydride monomer and octa (aminophenyltrioxysilane), wherein the diamine monomer is 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and fluorine-containing diamine, and the dianhydride monomer is pyromellitic dianhydride and fluorine-containing dianhydride. The invention also discloses a preparation method of the insulating polyimide film. The invention has good insulating property.
Description
Technical Field
The invention relates to the technical field of polyimide films, in particular to an insulating polyimide film and a preparation method thereof.
Background
Polyimide has good mechanical property, thermal stability and electrical property, is an important special high polymer material, and is widely applied to the microelectronic and photoelectric industries.
However, with the development of very large scale integrated circuits, the requirement for the insulation property of polyimide is also higher and higher. The dielectric constant of the conventional polyimide is about 3.5, and the dielectric property needs to be improved.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides an insulating polyimide film and a preparation method thereof.
The invention provides an insulating polyimide film, which comprises the following raw materials: diamine monomer, dianhydride monomer and octa (aminophenyltrioxysilane), wherein the diamine monomer is 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and fluorine-containing diamine, and the dianhydride monomer is pyromellitic dianhydride and fluorine-containing dianhydride.
Preferably, the fluorine-containing dianhydride is 4,4' - (hexafluoroisopropylidene) diphthalic anhydride.
Preferably, the fluorine-containing diamine is 2, 2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane.
Preferably, the molar ratio of the 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene to the fluorine-containing diamine is 0.6-0.7: 0.3-0.4.
Preferably, the molar ratio of the pyromellitic dianhydride to the fluorine-containing dianhydride is 0.5-0.6: 0.4-0.5.
Preferably, the octakis (aminophenyltrioxysilane) comprises 4 to 5 weight percent of the total weight of the diamine monomer and the dianhydride monomer.
Preferably, the molar ratio of diamine monomer to dianhydride monomer is 1: 0.9-1.
The invention also provides a preparation method of the insulating polyimide film, which comprises the following steps: in an inert gas atmosphere, uniformly mixing a diamine monomer and an organic solvent, then adding a dianhydride monomer for reaction, then adding an octa (aminophenyltrioxasilane) solution, and continuing to react to obtain an intermediate material; and defoaming the intermediate material, coating the defoamed intermediate material on the surface of a substrate, imidizing and demoulding to obtain the insulating polyimide film.
Preferably, the procedure for imidization is: heating to 100 ℃ and 110 ℃, and preserving heat for 1 h; then heating to 200 ℃ and 210 ℃, and preserving the heat for 0.5 h; then heating to 300 ℃ and 310 ℃, and preserving the heat for 20 min; then the temperature is raised to 350 ℃, and the temperature is kept for 10 min.
Preferably, the reaction is carried out for 5 to 7 hours at room temperature, then an octa (aminophenyltrioxasilane) solution is added, and the reaction is continued for 1.5 to 2 hours to obtain an intermediate material.
Preferably, the organic solvent is N, N-dimethylacetamide.
Has the advantages that:
the preparation method selects 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and 2, 2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane to be matched in a proper proportion as diamine monomers, pyromellitic dianhydride and 4,4' - (hexafluoroisopropylene) diphthalic anhydride to be matched in a proper proportion as dianhydride monomers, so that a proper amount of fluorine and a large-volume side group are introduced into polyimide, the dielectric constant of the polyimide can be greatly reduced, the insulating property of the polyimide is improved, and meanwhile, the heat resistance of the preparation method can be further improved due to the introduction of the fluorine; in addition, a proper amount of octa (aminophenyltrioxysilane) is added, so that the dielectric constant can be further reduced, and the mechanical property of the invention can be further improved; and the mechanical property of the film can be further improved by selecting a proper imidization process.
Detailed Description
The technical solution of the present invention will be described in detail below with reference to specific examples.
Example 1
An insulating polyimide film, the raw materials of which comprise: diamine monomers, dianhydride monomers and octa (aminophenyltrioxasilane), wherein the diamine monomers are 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and 2, 2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane, and the dianhydride monomers are pyromellitic dianhydride and 4,4' - (hexafluoroisopropylidene) diphthalic anhydride;
wherein the molar ratio of the 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene to the fluorine-containing diamine is 0.6: 0.4;
the molar ratio of pyromellitic dianhydride to fluorine-containing dianhydride is 0.5: 0.5;
the eight (aminophenyltrioxysilane) comprises 4% by weight of the total amount of diamine monomer and dianhydride monomer;
the molar ratio of diamine monomer to dianhydride monomer is 1: 1.
The preparation method of the insulating polyimide film comprises the following steps: in the nitrogen atmosphere, uniformly mixing a diamine monomer and N, N-dimethylacetamide, adding a dianhydride monomer, reacting at room temperature for 5 hours, adding an N, N-dimethylacetamide solution of octa (aminophenyltrioxasilane), and continuously reacting for 2 hours to obtain an intermediate material; defoaming the intermediate material, coating the intermediate material on the surface of a substrate, imidizing and demoulding to obtain the insulating polyimide film, wherein the imidizing procedure comprises the following steps: heating to 100 ℃, and keeping the temperature for 1 h; then heating to 200 ℃, and preserving heat for 0.5 h; then heating to 300 ℃, and preserving heat for 20 min; then the temperature is raised to 350 ℃, and the temperature is kept for 10 min.
Example 2
An insulating polyimide film, the raw materials of which comprise: diamine monomers, dianhydride monomers and octa (aminophenyltrioxasilane), wherein the diamine monomers are 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and 2, 2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane, and the dianhydride monomers are pyromellitic dianhydride and 4,4' - (hexafluoroisopropylidene) diphthalic anhydride;
wherein the molar ratio of the 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene to the fluorine-containing diamine is 0.7: 0.3;
the molar ratio of pyromellitic dianhydride to fluorine-containing dianhydride is 0.6: 0.4;
the eight (aminophenyltrioxysilane) comprises 5% by weight of the total amount of the diamine monomer and the dianhydride monomer;
the molar ratio of diamine monomer to dianhydride monomer is 1: 0.9.
The preparation method of the insulating polyimide film comprises the following steps: in the nitrogen atmosphere, uniformly mixing a diamine monomer and N, N-dimethylacetamide, adding a dianhydride monomer, reacting at room temperature for 7 hours, adding an N, N-dimethylacetamide solution of octa (aminophenyltrioxasilane), and continuously reacting for 1.5 hours to obtain an intermediate material; defoaming the intermediate material, coating the intermediate material on the surface of a substrate, imidizing and demoulding to obtain the insulating polyimide film, wherein the imidizing procedure comprises the following steps: heating to 110 ℃, and preserving heat for 1 h; then heating to 210 ℃, and preserving heat for 0.5 h; then heating to 310 ℃, and preserving heat for 20 min; then the temperature is raised to 350 ℃, and the temperature is kept for 10 min.
Example 3
An insulating polyimide film, the raw materials of which comprise: diamine monomers, dianhydride monomers and octa (aminophenyltrioxasilane), wherein the diamine monomers are 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and 2, 2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane, and the dianhydride monomers are pyromellitic dianhydride and 4,4' - (hexafluoroisopropylidene) diphthalic anhydride;
wherein the molar ratio of the 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene to the fluorine-containing diamine is 0.65: 0.35;
the molar ratio of pyromellitic dianhydride to fluorine-containing dianhydride is 0.55: 0.45;
the eight (aminophenyltrioxysilane) is 4.5% of the total weight of the diamine monomer and the dianhydride monomer;
the molar ratio of diamine monomer to dianhydride monomer is 1: 1.
The preparation method of the insulating polyimide film comprises the following steps: in the nitrogen atmosphere, uniformly mixing a diamine monomer and N, N-dimethylacetamide, adding a dianhydride monomer, reacting at room temperature for 6 hours, adding an N, N-dimethylacetamide solution of octa (aminophenyltrioxasilane), and continuously reacting for 1.8 hours to obtain an intermediate material; defoaming the intermediate material, coating the intermediate material on the surface of a substrate, imidizing and demoulding to obtain the insulating polyimide film, wherein the imidizing procedure comprises the following steps: heating to 105 ℃, and preserving heat for 1 h; then heating to 205 ℃, and preserving heat for 0.5 h; then heating to 305 ℃, and preserving the heat for 20 min; then the temperature is raised to 350 ℃, and the temperature is kept for 10 min.
The results of the tests performed in examples 1-3 are shown in the following table:
as can be seen from the above table, the invention has good insulation property, heat resistance and good light transmittance.
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 (10)
1. An insulating polyimide film, characterized in that its raw materials include: diamine monomer, dianhydride monomer and octa (aminophenyltrioxysilane), wherein the diamine monomer is 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene and fluorine-containing diamine, and the dianhydride monomer is pyromellitic dianhydride and fluorine-containing dianhydride.
2. The insulating polyimide film according to claim 1, wherein the fluorine-containing dianhydride is 4,4' - (hexafluoroisopropylidene) diphthalic anhydride.
3. The insulating polyimide film according to claim 1 or 2, wherein the fluorine-containing diamine is 2, 2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane.
4. The insulating polyimide film according to any one of claims 1 to 3, wherein the molar ratio of 9, 9-bis [4- (4-aminophenoxy) phenyl ] fluorene to fluorine-containing diamine is 0.6 to 0.7:0.3 to 0.4.
5. The insulating polyimide film according to any one of claims 1 to 4, wherein the molar ratio of pyromellitic dianhydride to fluorine-containing dianhydride is 0.5 to 0.6:0.4 to 0.5.
6. The insulating polyimide film according to any one of claims 1 to 5, wherein the octa (aminophenyltrioxysilane) is 4 to 5% by weight based on the total weight of the diamine monomer and the dianhydride monomer.
7. The insulating polyimide film according to any one of claims 1 to 6, wherein a molar ratio of the diamine monomer to the dianhydride monomer is 1:0.9 to 1.
8. A method for preparing an insulating polyimide film according to any one of claims 1 to 7, comprising the steps of: in an inert gas atmosphere, uniformly mixing a diamine monomer and an organic solvent, then adding a dianhydride monomer for reaction, then adding an octa (aminophenyltrioxasilane) solution, and continuing to react to obtain an intermediate material; and defoaming the intermediate material, coating the defoamed intermediate material on the surface of a substrate, imidizing and demoulding to obtain the insulating polyimide film.
9. The method for preparing an insulating polyimide film according to claim 8, wherein the imidization procedure is: heating to 100 ℃ and 110 ℃, and preserving heat for 1 h; then heating to 200 ℃ and 210 ℃, and preserving the heat for 0.5 h; then heating to 300 ℃ and 310 ℃, and preserving the heat for 20 min; then the temperature is raised to 350 ℃, and the temperature is kept for 10 min.
10. The method for preparing the insulating polyimide film according to claim 8 or 9, wherein the reaction is carried out for 5 to 7 hours at room temperature, then an octa (aminophenyltrioxasilane) solution is added, and the reaction is continued for 1.5 to 2 hours to obtain an intermediate material; preferably, the organic solvent is N, N-dimethylacetamide.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116178714A (en) * | 2023-02-28 | 2023-05-30 | 武汉理工大学 | Fluorine-containing modified polyimide and preparation method and application thereof |
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| CN110372899A (en) * | 2019-07-26 | 2019-10-25 | 南京理工大学 | A kind of colorless and transparent heat-proof polyimide film of high hydrophobicity and preparation method thereof |
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| CN116178714A (en) * | 2023-02-28 | 2023-05-30 | 武汉理工大学 | Fluorine-containing modified polyimide and preparation method and application thereof |
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Application publication date: 20200911 |