CN115010969B - Polyimide film for general glue-free flexible copper-clad plate and preparation method thereof - Google Patents
Polyimide film for general glue-free flexible copper-clad plate and preparation method thereof Download PDFInfo
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- 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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- 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
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- 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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- 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 discloses a polyimide film for a general glue-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 stirring condition, dianhydride monomers are added into the first solution in a divided manner until the reaction is complete, and a polyamide acid solution with the solid content of 15wt% is obtained; coating the polyamic acid solution, and performing imidization reaction to obtain a polyimide film; the invention adopts condensation copolymerization synthesis technology, introduces rigid structural groups capable of improving heat resistance and reducing thermal expansion and groups favorable for improving cohesiveness into polyimide main chain, and reduces the linear expansion coefficient of polyimide film and improves soldering temperature and peeling strength by optimizing raw material proportion and technological parameters.
Description
Technical Field
The invention belongs to the technical field of polyimide films, and particularly relates to a polyimide film for a general glue-free flexible copper-clad plate and a preparation method thereof.
Background
Flexible Printed Circuits (FPCs), which are a special base material for electronic interconnections, have the distinct characteristics of thinness, lightness, and flexibility in structure, and can be bent, curled, folded, etc., dynamically in addition to being bent statically. In recent years, with the rapid development of the electronic industry, electronic products are further developed toward miniaturization, light weight and high-density assembly, and the high-tech electronic products are directly promoted to adopt FPCs (flexible printed circuits) in large quantities, such as folding mobile phones, digital cameras, digital video cameras, automobile satellite positioning devices, liquid crystal televisions, notebook computers, on-load IC substrates and the like. Therefore, the market for Flexible Copper Clad Laminate (FCCL) as an important substrate for manufacturing FPC is also rapidly expanding.
Flexible copper clad laminates are generally classified into two types, glued and non-glued. The glued FCCL consists of three layers of copper foil, organic adhesive and polyimide film. The organic adhesive layer with poor thermal stability exists in the structure, so that the relative thermal dimensional stability of the flexible copper clad laminate is poor. In order to improve the thermal dimensional stability of the flexible copper clad laminate, a glue-free flexible copper clad laminate with an adhesive layer removed is produced.
The general glue-free flexible copper-clad plate consists of two layers of copper foil and polyimide film. The polyimide in the general glue-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 by the conventional general glue-free flexible copper clad laminate is poor in dimensional stability, soldering resistance and cohesiveness, and has the characteristics of high linear expansion coefficient, low soldering temperature resistance and low peeling strength, so that the flexible copper clad laminate is poor in performance, poor in use effect and limited in application.
Disclosure of Invention
The invention aims to provide a polyimide film for a general glue-free flexible copper-clad plate and a preparation method thereof, wherein a condensation copolymerization synthesis technology is adopted, and the raw material proportion and the technological parameters are optimized to reduce the linear expansion coefficient of the polyimide film and improve the soldering temperature resistance and the peeling strength.
The invention adopts the following technical scheme: the preparation method of the polyimide film for the universal glue-free flexible copper-clad plate comprises the following steps:
dissolving diamine monomer in an organic solvent to obtain a first solution;
under the stirring condition, dianhydride monomers are added into the first solution in a divided manner until the reaction is complete, and a polyamide acid solution with the solid content of 15wt% is obtained;
coating the polyamic acid solution, and performing imidization reaction to obtain a polyimide film;
wherein, after the dianhydride monomers are added into the first solution in a divided way, the dianhydride monomers and the diamine monomers undergo polycondensation and copolymerization reaction, and the reaction temperature of the polycondensation and copolymerization reaction is 0-35 ℃.
Further, the step of adding the dianhydride-type monomer to the first solution in portions includes:
calculating the heat release amount of the unit quantity of diamine monomers and dianhydride monomers for polycondensation and copolymerization reaction;
calculating the addition amount of dianhydride monomers to be added each time according to the heat release amount and the amount of the first solution;
wherein the addition amount of the dianhydride monomer satisfies the following conditions:
the exothermic amount after the dianhydride monomer is added into the first solution increases the temperature of the first solution to 35 ℃ or lower.
Further, before obtaining the polyamic acid solution with a solid content of 15wt%, the method further comprises:
an organic solvent is added to the first solution.
Further, the dianhydride monomer comprises two of a benzene 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',4' -biphenyl tetracarboxylic dianhydride.
Further, the ester bond-containing benzene dianhydride monomer is (4-phthalic anhydride) formyloxy-4-phthalate.
Further, the organic solvent is one of N-methylpyrrolidone, N '-dimethylformamide and N, N' -dimethylacetamide.
Further, the diamine monomer includes benzimidazole diamine monomer and biphenyl amide diamine monomer.
Another technical scheme of the invention is as follows: a polyimide film for a general glue-free flexible copper-clad plate is prepared by the method.
The beneficial effects of the invention are as follows: the invention adopts condensation copolymerization synthesis technology, introduces rigid structural groups capable of improving heat resistance and reducing thermal expansion and groups favorable for improving cohesiveness into polyimide main chain, and reduces the linear expansion coefficient of polyimide film and improves soldering temperature and peeling strength by optimizing raw material proportion and technological 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 glue-free flexible copper-clad plate, which comprises the following steps: dissolving diamine monomer in an organic solvent to obtain a first solution; under the condition of stirring, adding dianhydride monomers into the first solution in batches until the reaction is complete to obtain a polyamic acid solution with the solid content of 15wt%, and carrying out imidization reaction after coating the polyamic acid solution to obtain a polyimide film; wherein, after the dianhydride monomers are added into the first solution in a divided way, the dianhydride monomers and the diamine monomers undergo polycondensation and copolymerization reaction, and the reaction temperature of the polycondensation and copolymerization reaction is 0-35 ℃.
The invention adopts condensation copolymerization synthesis technology, introduces rigid structural groups capable of improving heat resistance and reducing thermal expansion and groups favorable for improving cohesiveness into polyimide main chain, and reduces the linear expansion coefficient of polyimide film and improves soldering temperature and peeling strength by optimizing raw material proportion and technological parameters.
In one embodiment, the step of adding the dianhydride-type monomer to the first solution in portions includes: calculating the heat release amount of the unit quantity of diamine monomers and dianhydride monomers for polycondensation and copolymerization reaction; calculating the addition amount of dianhydride monomers to be added each time according to the heat release amount and the amount of the first solution; wherein the addition amount of the dianhydride monomer satisfies the following conditions: and heating the first solution to 35 ℃ or lower by the exothermic amount after the dianhydride monomer is added into the first solution.
Specifically, the number of times of adding the dianhydride monomer is preferably 2-4 times, and the reaction time is 8-12 hours after the dianhydride monomer is added, so that the reaction can be completed.
Since the polycondensation copolymerization reaction is an exothermic reaction, the temperature of the solution increases during the reaction, and therefore, in order to control the reaction temperature, the present invention controls the exothermic amount of the reaction and thus the reaction temperature by controlling the amount of the dianhydride monomer to be added. Specifically, there are multiple calculation modes, such as measurement by an experiment method, calculation according to the change of the mass energy, calculation according to the magnitude of the substantial bond energy of the reaction, and the like.
In this example, the polyamide acid solution having a solid content of 15wt% was obtained by further comprising: an organic solvent is added to the first solution. Further, the polyamic acid solution of the target concentration can be obtained by adjusting the amount of the organic solvent.
In addition, the selection of the respective components in the present invention is also given as a preferable example, for example, the dianhydride monomer includes two of a benzene 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.
Specifically, the pyromellitic dianhydride monomer is pyromellitic dianhydride, and the structural formula isThe biphenyl dianhydride monomer is 2, 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 the embodiment of the invention, the diamine monomer comprises benzimidazole diamine monomer and biphenyl amide diamine monomer, and the molar ratio of the benzimidazole diamine monomer to the biphenyl amide diamine monomer is (1-2): 1. the benzimidazole diamine monomer is 2- (4-aminophenyl) -5-aminobenzimidazole, and has the structural formula ofThe biphenyl amide diamine monomer is N, N ' - [1,1' -biphenyl-4, 4' -bis (4-aminobenzamide)]The structural formula is->
In the present invention, the organic solvent is one of N-methylpyrrolidone, N '-dimethylformamide and N, N' -dimethylacetamide.
In an embodiment of the present invention, the imidization procedure is preferably: 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min.
Example 1:
(1) 15mmol of pyromellitic dianhydride and 15mmol of 2, 3',4' -biphenyl tetracarboxylic dianhydride are added into an N, N '-dimethylacetamide solution containing 15mmol of 2- (4-aminophenyl) -5-aminobenzimidazole and 15mmol of N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] for 3 times under the protection of nitrogen and stirring, the reaction temperature is controlled to be 0-35 ℃ and the reaction is carried out for 8 hours, so as to obtain the polyamide 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 then imidized at a temperature. Wherein, imidization parameters are: 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min. Thereafter, the film was cooled and removed to obtain polyimide films E1 and E1 having a thickness of 25. Mu.m, and the test methods and data are shown in Table 1.
Example 2:
(1) Under the protection of nitrogen and stirring, 15mmol (4-phthalic anhydride) formyloxy-4-phthalic acid ester and 15mmol 2, 3',4' -biphenyl tetracarboxylic dianhydride are added into an N, N '-dimethylformamide solution containing 15mmol 2- (4-aminophenyl) -5-aminobenzimidazole and 15mmol N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] for 2 times, the reaction temperature is controlled between 0 and 35 ℃ and the reaction time is 10 hours, so as to obtain a polyamide 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 then imidized at a temperature. Wherein, imidization parameters are: 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min. Thereafter, the film was cooled and removed to obtain polyimide films E2 and E2 having a thickness of 25. Mu.m, and the test methods and data are shown in Table 1.
Example 3:
(1) Adding 15mmol (4-phthalic anhydride) formyloxy-4-phthalic acid ester and 15mmol pyromellitic dianhydride into an N-methyl pyrrolidone solution containing 15mmol 2- (4-aminophenyl) -5-aminobenzimidazole and 15mmol N, N ' - [1,1' -biphenyl-4, 4' -bis (4-aminobenzamide) ] for 4 times under the protection of nitrogen and stirring, controlling the reaction temperature at 0-35 ℃ and the reaction time at 12 hours to obtain a polyamide 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 then imidized at a temperature. Wherein, imidization parameters are: 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min. Thereafter, the film was cooled and removed to obtain polyimide films E3 and E3 having a thickness of 25. Mu.m, and the test methods and data for the performance are shown in Table 1.
Example 4:
(1) Under the protection of nitrogen and stirring, 15mmol of pyromellitic dianhydride and 15mmol of 2, 3',4' -biphenyl tetracarboxylic dianhydride are added into an N, N '-dimethylformamide solution containing 20mmol of 2- (4-aminophenyl) -5-aminobenzimidazole and 10mmol of N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] for 4 times, the reaction temperature is controlled at 0-35 ℃ and the reaction time is 8 hours, so as to obtain a polyamide 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 then imidized at a temperature. Wherein, imidization parameters are: 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min. Thereafter, the film was cooled and removed to obtain polyimide films E4 and E4 having a thickness of 25. Mu.m, and the test methods and data are shown in Table 1.
Example 5:
(1) Under the protection of nitrogen and stirring, 4, 15mmol (4-phthalic anhydride) formyloxy-4-phthalic acid ester and 15mmol 2, 3',4' -biphenyl tetracarboxylic dianhydride are poured into an N-methyl pyrrolidone solution dissolved with 20mmol 2- (4-aminophenyl) -5-aminobenzimidazole and 10mmol N, N ' - [1,1' -biphenyl-4, 4' -bis (4-aminobenzamide) ] to obtain a polyamide acid solution with the solid content of 15wt percent, wherein the reaction temperature is controlled to be 0-35 ℃ and the reaction time is 10 hours;
(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 then imidized at a temperature. Wherein the imidization parameter is 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min. Thereafter, the film was cooled and removed to obtain polyimide films E5 and E5 having a thickness of 25. Mu.m, and the test methods and data 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 containing 20mmol of 2- (4-aminophenyl) -5-aminobenzimidazole and 10mmol of N, N' - [1,1 '-biphenyl-4, 4' -bis (4-aminobenzamide) ] under the condition that the reaction temperature is controlled between 0 and 35 ℃ and the reaction time is 12 hours, so as to obtain a polyamide 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 then imidized at a temperature. Wherein, imidization parameters are: 80 ℃/5min, 120 ℃/5min, 150 ℃/5min, 180 ℃/5min, 200 ℃/5min, 250 ℃/5min, 300 ℃/4min, 350 ℃/4min, 400 ℃/3min. Thereafter, the film was cooled and removed to obtain polyimide films E6 and E6 having a thickness of 25. Mu.m, and the test methods and data are shown in Table 1.
Table 1 shows the main performance data and test method of polyimide film prepared in examples
The invention also discloses a polyimide film for the universal glue-free flexible copper-clad plate, which is prepared by adopting 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 peeling strength not less than 1.5N/mm.
Claims (7)
1. The preparation method of the polyimide film for the universal glue-free flexible copper-clad plate is characterized by comprising the following steps of:
dissolving diamine monomer in an organic solvent to obtain a first solution;
under the stirring condition, the dianhydride monomers are added into the first solution in a divided manner until the reaction is complete, wherein the addition amount of each time is 25% -33.3% of the total mole number of the dianhydride monomers, and a polyamide acid solution with the solid content of 15wt% is obtained;
coating the polyamic acid solution, and performing imidization reaction to obtain a polyimide film;
after the dianhydride monomer is added into the first solution in a divided manner, the dianhydride monomer and the diamine monomer undergo polycondensation and copolymerization, wherein the diamine monomer comprises benzimidazole diamine monomer and bisamide diamine monomer; the dianhydride monomer comprises two of a benzene 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; the reaction temperature of the polycondensation and copolymerization reaction is 0-35 ℃;
the step of adding dianhydride monomer to the first solution comprises the steps of:
calculating the heat release amount of the polycondensation and copolymerization reaction of the diamine monomer and the dianhydride monomer in unit quantity;
calculating the addition amount of the dianhydride monomer to be added each time according to the heat release amount and the amount of the first solution;
wherein the addition amount of the dianhydride monomer satisfies the following conditions:
and heating the first solution to 35 ℃ or lower by the exothermic amount after the dianhydride monomer is added into the first solution.
2. The method for preparing a polyimide film for a universal glue-free flexible copper-clad plate according to claim 1, wherein before obtaining the polyamic acid solution with the solid content of 15wt%, the method further comprises:
an organic solvent is added to the first solution.
3. The method for preparing the polyimide film for the universal glue-free flexible copper-clad plate according to claim 2, wherein the pyromellitic dianhydride monomer is pyromellitic dianhydride.
4. The method for preparing a polyimide film for a universal glue-free flexible copper-clad plate according to claim 3, wherein the biphenyl dianhydride monomer is-biphenyl tetracarboxylic dianhydride.
5. The method for preparing the polyimide film for the universal glue-free flexible copper-clad plate, according to claim 2, wherein the benzene dianhydride monomer containing ester bonds is (4-phthalic anhydride) formyloxy-4-phthalate.
6. The method for preparing a polyimide film for a universal glue-free flexible copper-clad plate according to any one of claims 3 to 5, wherein the organic solvent is one of N-methylpyrrolidone, N '-dimethylformamide and N, N' -dimethylacetamide.
7. A polyimide film for a general glue-free flexible copper-clad plate, which is characterized in that the polyimide film is prepared by the method of any one of claims 1 to 6.
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CN104842625A (en) * | 2015-05-21 | 2015-08-19 | 成都多吉昌新材料有限公司 | Preparation method of two-layer dielectric adhesive-free flexible copper clad laminate |
WO2019093669A2 (en) * | 2017-11-10 | 2019-05-16 | 에스케이씨코오롱피아이 주식회사 | Ultra-thin black polyimide film and manufacturing method therefor |
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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DE60125049D1 (en) * | 2000-08-24 | 2007-01-18 | Du Pont | POLYIMIDE FILM, HOLDING METHOD, AND METAL CONDUCTORS WITH POLYIMIDE SUBSTRATE |
CN103739842A (en) * | 2013-12-20 | 2014-04-23 | 深圳瑞华泰薄膜科技有限公司 | Thermoplastic polyimide and method for preparing flexible copper-clad plate from thermoplastic polyimide |
CN104842625A (en) * | 2015-05-21 | 2015-08-19 | 成都多吉昌新材料有限公司 | Preparation method of two-layer dielectric adhesive-free flexible copper clad laminate |
WO2019093669A2 (en) * | 2017-11-10 | 2019-05-16 | 에스케이씨코오롱피아이 주식회사 | Ultra-thin black polyimide film and manufacturing method therefor |
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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