CN115010969A - Polyimide film for general adhesive-free flexible copper clad laminate and preparation method thereof - Google Patents
Polyimide film for general adhesive-free flexible copper clad laminate and preparation method thereof Download PDFInfo
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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
- 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
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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
- 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 a polyimide film for a general adhesive-free flexible copper-clad plate and a preparation method thereof, wherein diamine monomers are dissolved in an organic solvent to obtain a first solution; under the condition of stirring, adding dianhydride monomers into the first solution in several times until the reaction is complete to obtain a polyamic acid solution with the solid content of 15 wt%; coating a polyamic acid solution, and then carrying out imidization reaction to obtain a polyimide film; the invention adopts a condensation copolymerization synthesis technology, introduces rigid structural groups capable of improving heat resistance and reducing thermal expansion and groups beneficial to improving cohesiveness to a polyimide main chain, and reduces the linear expansion coefficient of a polyimide film and improves the soldering temperature resistance and the peeling strength by optimizing the raw material proportion and the process parameters.
Description
Technical Field
The invention belongs to the technical field of polyimide films, and particularly relates to a polyimide film for a general adhesive-free flexible copper-clad plate and a preparation method thereof.
Background
As a special base material for electronic interconnection, a Flexible Printed Circuit (FPC) has the distinctive features of thinness, lightness, and flexible structure, and can be bent statically, dynamically, curled, folded, and the like. In recent years, with the rapid development of the electronic industry, electronic products are further miniaturized, light-weighted and densely assembled, and the adoption of a large amount of FPCs, such as folding mobile phones, digital cameras, digital video cameras, automobile satellite orientation devices, liquid crystal televisions, notebook computers, and IC-on-tape substrates, is directly promoted. Therefore, the market of Flexible Copper Clad Laminates (FCCL) as important substrates for manufacturing FPCs is also rapidly expanding.
Flexible copper clad laminates are generally classified into adhesive and non-adhesive types. The glued FCCL is composed of three layers of copper foil, organic adhesive and polyimide film. The relative thermal dimensional stability of the flexible copper clad laminate is poor due to the existence of the organic adhesive layer with poor thermal stability in the structure. In order to improve the thermal dimensional stability of the flexible copper clad laminate, a non-adhesive flexible copper clad laminate without an adhesive layer is produced.
The general adhesive-free flexible copper clad laminate consists of two layers, namely a copper foil and a polyimide film. The polyimide in the general adhesive-free flexible copper clad laminate is required to have good high temperature resistance, dimensional stability, soldering resistance, cohesiveness, insulating property, folding resistance and mechanical property. However, the polyimide film used in the existing general adhesive-free flexible copper clad laminate has poor dimensional stability, soldering resistance and cohesiveness, which are reflected in high linear expansion coefficient, low soldering temperature resistance and low peel strength, resulting in poor performance, poor use effect and limited application of the flexible copper clad laminate.
Disclosure of Invention
The invention aims to provide a polyimide film for a general adhesive-free flexible copper-clad plate and a preparation method thereof.
The invention adopts the following technical scheme: a preparation method of a polyimide film for a general adhesive-free flexible copper clad laminate comprises the following steps:
dissolving diamine monomer in organic solvent to obtain first solution;
under the condition of stirring, adding dianhydride monomers into the first solution in several times until the reaction is complete to obtain a polyamic acid solution with the solid content of 15 wt%;
coating a polyamic acid solution, and then carrying out imidization reaction to obtain a polyimide film;
after the dianhydride monomers are added into the first solution in several times, the dianhydride monomers and the diamine monomers are subjected to polycondensation copolymerization reaction, wherein the reaction temperature of the polycondensation copolymerization reaction is 0-35 ℃.
Further, the dianhydride monomer is added into the first solution in portions including:
calculating the heat release of the unit amount of diamine monomers and dianhydride monomers in the polycondensation copolymerization reaction;
calculating the addition amount of the dianhydride monomer to be added each time according to the exothermic amount and the amount of the first solution;
wherein the addition amount of the dianhydride monomer meets the following conditions:
the exothermic amount of the dianhydrides monomer added to the first solution is such that the temperature of the first solution is raised to 35 ℃ or less.
Further, before obtaining the polyamic acid solution with the solid content of 15 wt%, the method further comprises the following steps:
an organic solvent is added to the first solution.
Further, the dianhydride monomer comprises two of a pyromellitic dianhydride monomer, a biphenyl dianhydride monomer and a benzene dianhydride monomer containing an ester bond, and the molar ratio of the two dianhydride monomers is 1: 1.
Further, the pyromellitic dianhydride monomer is pyromellitic dianhydride.
Further, the biphenyl dianhydride monomer is 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride.
Further, the benzene dianhydride monomer containing ester bonds is (4-phthalic anhydride) formyloxy-4-phthalic acid ester.
Further, the organic solvent is one of N-methylpyrrolidone, N '-dimethylformamide and N, N' -dimethylacetamide.
Further, the diamine monomer comprises benzimidazole diamine monomer and benzidine diamine monomer.
The other technical scheme of the invention is as follows: the polyimide film is prepared by the method.
The beneficial effects of the invention are: the invention adopts a condensation copolymerization synthesis technology, introduces rigid structural groups capable of improving heat resistance and reducing thermal expansion and groups beneficial to improving cohesiveness to a polyimide main chain, and reduces the linear expansion coefficient of a polyimide film and improves the soldering temperature resistance and the peeling strength by optimizing the raw material proportion and the process parameters.
Detailed Description
The present invention will be described in detail with reference to the following embodiments.
The invention discloses a preparation method of a polyimide film for a general adhesive-free flexible copper clad laminate, which comprises the following steps: dissolving diamine monomer in organic solvent to obtain first solution; under the condition of stirring, adding dianhydride monomers into the first solution in several times until the reaction is complete to obtain a polyamic acid solution with the solid content of 15 wt%, and coating the polyamic acid solution and then carrying out imidization reaction to obtain a polyimide film; after the dianhydride monomer is added into the first solution in multiple times, the dianhydride monomer and the diamine monomer are subjected to polycondensation copolymerization reaction, wherein the reaction temperature of the polycondensation copolymerization reaction is 0-35 ℃.
The invention adopts a condensation copolymerization synthesis technology, introduces rigid structural groups capable of improving heat resistance and reducing thermal expansion and groups beneficial to improving cohesiveness to a polyimide main chain, and reduces the linear expansion coefficient of a polyimide film and improves the soldering temperature resistance and the peeling strength by optimizing the raw material proportion and the process parameters.
In one embodiment, adding the dianhydride-based monomer to the first solution in portions comprises: calculating the heat release of the unit amount of diamine monomers and dianhydride monomers in the polycondensation copolymerization reaction; calculating the addition amount of the dianhydride monomer to be added each time according to the exothermic amount and the amount of the first solution; wherein the addition amount of the dianhydride monomer meets the following conditions: the exothermic amount of the dianhydrides monomer added to the first solution is such that the temperature of the first solution is raised to 35 ℃ or less.
Specifically, the adding times of the dianhydride monomer are preferably 2-4 times, the reaction time is 8-12 hours after the dianhydride monomer is added, and the reaction can be completed in this period of time.
Since the polycondensation copolymerization reaction is an exothermic reaction and the temperature of the solution increases during the reaction, the amount of heat generated by the reaction and thus the reaction temperature can be controlled by controlling the amount of dianhydride monomer added in the present invention in order to control the reaction temperature. Specifically, there are multiple calculation methods, such as an experimental measurement, a calculation based on a change in energy of a substance, a calculation based on a magnitude of a reaction-essential bond energy, and the like.
In this example, the polyamide acid solution with a solids content of 15 wt% was obtained by: an organic solvent is added to the first solution. Further, the amount of the organic solvent can be adjusted to obtain a polyamic acid solution having a desired concentration.
In addition, preferred examples are also given for the selection of the respective components in the present invention, for example, the dianhydride-based monomer includes two of the pyromellitic dianhydride monomer, the biphenyl dianhydride-based monomer and the benzene dianhydride-based monomer containing an ester bond, and the molar ratio of the two dianhydride monomers is 1: 1.
Specifically, the pyromellitic dianhydride monomer is pyromellitic dianhydride with the structural formula
The biphenyl dianhydride monomer is 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride and has the structural formula
The benzene dianhydride monomer containing ester bond is (4-phthalic anhydride) formyloxy-4-phthalic acid ester, and the structural formula is
In embodiments of the invention, the diamine monomers comprise benzimidazolesDiamine monomer and benzidine diamine monomer, and the molar ratio of the diamine monomer to the benzidine diamine monomer is (1-2): 1. the benzimidazole diamine monomer is 2- (4-aminophenyl) -5-aminobenzimidazole, and the structural formula is
The benzidine diamine monomer is N, N ' - [1,1 ' -biphenyl-4, 4 ' -bis (4-aminobenzamide)]Having a structural formula of
In the present invention, the organic solvent is one of N-methylpyrrolidone, N '-dimethylformamide and N, N' -dimethylacetamide.
In the present embodiment, the imidization procedure is preferably: 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min.
Example 1:
(1) under the protection of nitrogen and stirring, adding 15mmol of pyromellitic dianhydride and 15mmol of 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride into an N, N '-dimethylacetamide solution dissolved with 15mmol of 2- (4-aminophenyl) -5-aminobenzimidazole and 15mmol of N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] for 3 times, controlling the reaction temperature at 0-35 ℃, and reacting for 8 hours to obtain a polyamic acid solution with the solid content of 15 wt%.
(2) The obtained polyamic acid solution was coated on a glass plate, and the glass plate was placed in an explosion-proof drying oven and heated to imidize. Wherein the imidization parameters are as follows: 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min. Then, the film was cooled and removed to obtain a polyimide film E1 having a thickness of 25 μm, and the performance test method and data of E1 are shown in Table 1.
Example 2:
(1) under the protection of nitrogen and stirring, adding 15mmol (4-phthalic anhydride) formyloxy-4-phthalic acid ester and 15mmol 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride into an N, N '-dimethylformamide solution dissolved with 15mmol 2- (4-aminophenyl) -5-aminobenzimidazole and 15mmol N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] for 2 times, controlling the reaction temperature at 0-35 ℃, and reacting for 10 hours to obtain a polyamic acid solution with the solid content of 15 wt%;
(2) the obtained polyamic acid solution was coated on a glass plate, and the glass plate was placed in an explosion-proof drying oven and heated to imidize. Wherein the imidization parameters are as follows: 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min. Then, the film was cooled and removed to obtain a polyimide film E2 having a thickness of 25 μm, and the performance test method and data of E2 are shown in Table 1.
Example 3:
(1) under the protection of nitrogen and stirring, adding 15mmol (4-phthalic anhydride) formyloxy-4-phthalic acid ester and 15mmol pyromellitic dianhydride into an N-methylpyrrolidone solution dissolved with 15mmol 2- (4-aminophenyl) -5-aminobenzimidazole and 15mmol N, N ' - [1,1 ' -biphenyl-4, 4 ' -bis (4-aminobenzamide) ] for 4 times, controlling the reaction temperature at 0-35 ℃, and reacting for 12 hours to obtain a polyamic acid solution with the solid content of 15 wt%;
(2) the obtained polyamic acid solution was coated on a glass plate, and the glass plate was placed in an explosion-proof drying oven and heated to imidize. Wherein the imidization parameters are as follows: 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min. Then, the film was cooled and removed to obtain a polyimide film E3 having a thickness of 25 μm, and the performance test method and data of E3 are shown in Table 1.
Example 4:
(1) under the protection of nitrogen and stirring, adding 15mmol of pyromellitic dianhydride and 15mmol of 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride into an N, N '-dimethylformamide solution dissolved with 20mmol of 2- (4-aminophenyl) -5-aminobenzimidazole and 10mmol of N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] for 4 times, controlling the reaction temperature to be 0-35 ℃, and reacting for 8 hours to obtain a polyamic acid solution with the solid content of 15 wt%;
(2) the obtained polyamic acid solution was coated on a glass plate, and the glass plate was placed in an explosion-proof drying oven and heated to imidize. Wherein the imidization parameters are as follows: 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min. Then, the film was cooled and removed to obtain a polyimide film E4 having a thickness of 25 μm, and the performance test method and data of E4 are shown in Table 1.
Example 5:
(1) under the protection of nitrogen and stirring, pouring 15mmol (4-phthalic anhydride) formyloxy-4-phthalic acid ester and 15mmol 2,3,3 ', 4 ' -biphenyl tetracarboxylic dianhydride into an N-methylpyrrolidone solution dissolved with 20mmol 2- (4-aminophenyl) -5-aminobenzimidazole and 10mmol N, N ' - [1,1 ' -biphenyl-4, 4 ' -bis (4-aminobenzamide) ] for 10 hours in 4 minutes, controlling the reaction temperature at 0-35 ℃, and obtaining a polyamic acid solution with the solid content of 15 wt%;
(2) the obtained polyamic acid solution was coated on a glass plate, and the glass plate was placed in an explosion-proof drying oven and heated to imidize. Wherein the imidization parameters are 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min. Then, the film was cooled and removed to obtain a polyimide film E5 having a thickness of 25 μm, and the performance test method and data of E5 are shown in Table 1.
Example 6:
(1) under the protection of nitrogen and stirring, adding 15mmol of pyromellitic dianhydride and 15mmol of (4-phthalic anhydride) formyloxy-4-phthalic acid ester into an N, N '-dimethylacetamide solution dissolved with 20mmol of 2- (4-aminophenyl) -5-aminobenzimidazole and 10mmol of N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] by 3 minutes, controlling the reaction temperature at 0-35 ℃ and the reaction time at 12 hours to obtain a polyamic acid solution with the solid content of 15 wt%;
(2) the obtained polyamic acid solution was coated on a glass plate, and the glass plate was placed in an explosion-proof drying oven and heated to imidize. Wherein the imidization parameters are as follows: 80 ℃/5min → 120 ℃/5min → 150 ℃/5min → 180 ℃/5min → 200 ℃/5min → 250 ℃/5min → 300 ℃/4min → 350 ℃/4min → 400 ℃/3 min. Then, the film was cooled and removed to obtain a polyimide film E6 having a thickness of 25 μm, and the performance test method and data of E6 are shown in Table 1.
TABLE 1 Main Property data and test method of polyimide film prepared in example
The invention also discloses a polyimide film for the general adhesive-free flexible copper clad laminate, and the polyimide film is prepared by the method. The polyimide film prepared by the method has the linear thermal expansion coefficient not more than 22 ppm/DEG C, the soldering temperature not less than 300 ℃ (60 seconds) and the peel strength not less than 1.5N/mm.
Claims (10)
1. A preparation method of a polyimide film for a general adhesive-free flexible copper clad laminate is characterized by comprising the following steps:
dissolving diamine monomer in organic solvent to obtain first solution;
under the condition of stirring, adding dianhydride monomers into the first solution in several times until the reaction is complete to obtain a polyamic acid solution with the solid content of 15 wt%;
coating the polyamic acid solution, and then carrying out imidization reaction to obtain a polyimide film;
after the dianhydride monomer is added into the first solution in multiple times, the dianhydride monomer and the diamine monomer are subjected to polycondensation copolymerization reaction, wherein the reaction temperature of the polycondensation copolymerization reaction is 0-35 ℃.
2. The method for preparing the polyimide film for the general adhesive-free flexible copper-clad plate according to claim 1, wherein the step of adding the dianhydride monomer into the first solution comprises the steps of:
calculating the heat release of the unit amount of the diamine monomer and the dianhydride monomer in the polycondensation copolymerization reaction;
calculating the addition amount of the dianhydride monomer to be added each time according to the exothermic amount and the amount of the first solution;
wherein the addition amount of the dianhydride monomer meets the following conditions:
the exothermic amount after the dianhydride monomer is added into the first solution enables the temperature of the first solution to be raised to be less than or equal to 35 ℃.
3. The method for preparing the polyimide film for the general flexible copper clad laminate according to claim 2, wherein the step of obtaining the polyamic acid solution with the solid content of 15 wt% further comprises the following steps:
adding an organic solvent to the first solution.
4. The method for preparing the polyimide film for the general adhesive-free flexible copper-clad plate according to claim 2 or 3, wherein the dianhydride monomers comprise two of pyromellitic dianhydride monomers, biphenyl dianhydride monomers and ester bond-containing benzene dianhydride monomers, and the molar ratio of the two dianhydride monomers is 1: 1.
5. The method for preparing the polyimide film for the general adhesive-free flexible copper-clad plate according to claim 4, wherein the pyromellitic dianhydride monomer is pyromellitic dianhydride.
6. The method for preparing the polyimide film for the general adhesive-free flexible copper-clad plate according to claim 4, wherein the biphenyl dianhydride monomer is 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride.
7. The method for preparing the polyimide film for the general flexible copper clad laminate according to claim 4, wherein the benzene dianhydride monomer containing ester bond is (4-phthalic anhydride) formyloxy-4-phthalate.
8. The method for preparing the polyimide film for the general adhesive-free flexible copper-clad plate according to any one of claims 5 to 7, wherein the organic solvent is one of N-methylpyrrolidone, N '-dimethylformamide and N, N' -dimethylacetamide.
9. The method for preparing the polyimide film for the general adhesive-free flexible copper-clad plate according to any one of claims 5 to 7, wherein the diamine monomer comprises benzimidazole diamine monomer and benzidine diamine monomer.
10. A polyimide film for a general adhesive-free flexible copper clad laminate is characterized in that the polyimide film is prepared by the method of any one of claims 1 to 9.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115710352A (en) * | 2022-10-31 | 2023-02-24 | 浙江中科玖源新材料有限公司 | Binder for lithium ion battery silicon cathode and lithium ion battery silicon cathode |
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| CN112373150A (en) * | 2020-11-12 | 2021-02-19 | 西安航天三沃化学有限公司 | Preparation method of glue-free single-sided flexible copper-clad plate based on coating method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115710352A (en) * | 2022-10-31 | 2023-02-24 | 浙江中科玖源新材料有限公司 | Binder for lithium ion battery silicon cathode and lithium ion battery silicon cathode |
| CN115710352B (en) * | 2022-10-31 | 2024-04-16 | 浙江中科玖源新材料有限公司 | Binder for silicon negative electrode of lithium ion battery and silicon negative electrode of lithium ion battery |
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