WO2023189298A1 - Composition de résine, feuille de cuivre pourvue de résine, et matériau composite - Google Patents
Composition de résine, feuille de cuivre pourvue de résine, et matériau composite Download PDFInfo
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- WO2023189298A1 WO2023189298A1 PCT/JP2023/008657 JP2023008657W WO2023189298A1 WO 2023189298 A1 WO2023189298 A1 WO 2023189298A1 JP 2023008657 W JP2023008657 W JP 2023008657W WO 2023189298 A1 WO2023189298 A1 WO 2023189298A1
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- Prior art keywords
- resin
- weight
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- resin composition
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- 229920005989 resin Polymers 0.000 title claims abstract description 94
- 239000011347 resin Substances 0.000 title claims abstract description 94
- 239000011342 resin composition Substances 0.000 title claims abstract description 91
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 239000011889 copper foil Substances 0.000 title claims abstract description 50
- 239000002131 composite material Substances 0.000 title claims description 23
- 239000003822 epoxy resin Substances 0.000 claims abstract description 78
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 78
- 239000011521 glass Substances 0.000 claims abstract description 54
- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 239000000758 substrate Substances 0.000 claims abstract description 44
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229920001721 polyimide Polymers 0.000 claims abstract description 20
- 229920006122 polyamide resin Polymers 0.000 claims abstract description 15
- 239000009719 polyimide resin Substances 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 125000000524 functional group Chemical group 0.000 claims description 44
- 229910052802 copper Inorganic materials 0.000 claims description 30
- 239000010949 copper Substances 0.000 claims description 30
- 238000003860 storage Methods 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 26
- 238000003475 lamination Methods 0.000 abstract description 20
- 238000011156 evaluation Methods 0.000 description 21
- 239000000853 adhesive Substances 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 15
- 238000005259 measurement Methods 0.000 description 13
- 239000011888 foil Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000002966 varnish Substances 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 238000010030 laminating Methods 0.000 description 7
- 239000004642 Polyimide Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 101100330447 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) DAN1 gene Proteins 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000004843 novolac epoxy resin Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- -1 glycidyl ester Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920006259 thermoplastic polyimide Polymers 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004845 glycidylamine epoxy resin Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/088—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyamides
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
Definitions
- the present invention relates to a resin composition, a resin-coated copper foil, and a composite material.
- Patent Document 1 International Publication No. 2020/195661 describes (a) an acrylic polymer having a tensile modulus of 200 MPa or less, (b) a resin that is solid at 25°C, and (c) the component (a). and (b) a resin composition that is liquid at 25° C. and is crosslinkable with at least one of the components, and (d) a polymerization initiator, the resin composition comprising the components (a), (b), and (c).
- the content of (a) component is 35 parts by weight or more and 93 parts by weight or less, the content of component (b) is 3 parts by weight or more and 60 parts by weight or less, and (c A resin composition intended for application to a glass substrate is disclosed, in which the content of component ) is 1 part by weight or more and 25 parts by weight or less.
- Patent Document 2 Japanese Unexamined Patent Application Publication No. 2007-168123 discloses a method for manufacturing a flexible board with metal foil, in which metal foil is provided on at least one side of a resin film.
- a manufacturing method is disclosed, which includes a step of thermocompression bonding at a temperature of .degree. C. or more and 500.degree. C. or less, and the resin film contains a non-thermoplastic polyimide resin.
- Patent Document 3 International Publication No.
- 5-179220 discloses that (A) 100 parts by weight of a soluble aromatic polyamideimide, (B) 25 parts by weight or more and 300 parts by weight or less of an epoxy resin, and (C) an epoxy curing agent. discloses a heat-resistant adhesive that is contained as a resin component.
- resin compositions are used for various purposes, and as disclosed in Patent Documents 2 to 4, among printed wiring boards, for example, bonding of resin materials such as prepreg and metal foil, etc.
- a metal foil for example, copper foil
- a glass substrate are bonded together via a resin composition
- unique problems arise.
- the press method when creating a composite material by bonding a copper foil and a glass substrate together via a resin composition as a resin layer, using the press method will only take time and limit the size of the composite material itself. Otherwise, the glass substrate may break.
- the lamination method is a method of bonding two or more sheets roll-to-roll with lower pressure than the press method, so it can be produced continuously and there is less chance of the glass substrate breaking.
- the invention contains two or more polymers selected from polyamide resins, polyimide resins, and polyacrylic resins, an epoxy resin, and a curing agent, and that at least one of the two or more polymers has a weight average
- the resin composition which is a polymer with a molecular weight of 50,000 or more and at least one other polymer is a polymer with a weight average molecular weight of less than 50,000, enables adhesion of a copper foil and a glass substrate by a lamination method, and also has excellent heat resistance.
- an object of the present invention is to provide a resin composition that enables bonding of a copper foil and a glass substrate by a lamination method and has excellent heat resistance.
- Aspect 1 Two or more polymers selected from the group consisting of polyamide resin, polyimide resin, and polyacrylic resin, one or more epoxy resins; a hardening agent; Among the two or more types of polymers, At least one type is a polymer having a weight average molecular weight of 50,000 or more, A resin composition in which at least one other type is a polymer having a weight average molecular weight of less than 50,000.
- the epoxy resin includes two or more epoxy resins, and among the two or more epoxy resins, At least one type is an epoxy resin having a functional group number of 3 or more, The resin composition according to aspect 1 or 2, wherein at least one other type is an epoxy resin having less than 3 functional groups.
- At least one type is a polyamide resin, The resin composition according to any one of aspects 1 to 3, wherein at least one other type is a polyimide resin.
- Aspect 7 The resin composition according to any one of aspects 1 to 6, which contains the polymer having a weight average molecular weight of 50,000 or more in a proportion of 1 part by weight or more and 20 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition. .
- Aspect 8 The resin composition according to any one of aspects 1 to 7, wherein the resin composition has a storage modulus of 10 MPa or more at 200° C. in a C-stage state after curing.
- the copper layer has a thickness of 5 ⁇ m or less, and further comprises a carrier layer on a surface of the copper layer opposite to the smooth surface.
- a glass substrate a glass substrate; The resin-coated copper foil according to aspect 9 or 10, wherein the resin layer is provided on at least one surface of the glass substrate so as to be in contact with the glass substrate; Composite material with.
- the resin composition of the present invention contains two or more polymers selected from the group consisting of polyamide resins, polyimide resins, and polyacrylic resins, one or more epoxy resins, and a curing agent. At least one of these two or more types of polymers has a weight average molecular weight of 50,000 or more, and at least one other type has a weight average molecular weight of less than 50,000.
- the resin composition containing the two or more types of polymers, epoxy resin, and curing agent enables bonding of copper foil and glass substrate by lamination method, and exhibits excellent heat resistance.
- a resin composition with excellent heat resistance can withstand high temperatures when manufacturing products including the resin composition.
- the C-stage of the resin is not completed by laminating alone, and additional heat treatment for main curing is required. Even during this additional heat treatment, problems such as warping and cracking may occur. Furthermore, in post-processes, heating processes may be required for annealing, component mounting, etc., and heat resistance that can withstand such high temperatures during manufacturing is also desired.
- the properties such as heat resistance of the resin composition are, for example, the storage modulus at 200°C in the C stage state after curing, and the property of the composite material in which copper foil and glass substrate are bonded together via the resin composition. This can be determined by evaluating the degree of void generation, the adhesion and adhesive strength between the resin and the glass substrate or copper foil, and the degree of warpage.
- the resin composition of the present invention preferably has a storage modulus at 200°C of 10 MPa or more, more preferably 30 MPa or more, even more preferably 300 MPa or more in the C-stage state after curing.
- the storage modulus at 200° C. is preferably higher, and the upper limit is not particularly limited, but is typically 10,000 MPa or less, more typically 5,000 MPa or less, still more typically 1,000 MPa or less.
- the storage modulus at 200° C. is measured using a DMA (dynamic viscoelasticity measurement) device.
- the resin composition of the present invention contains two or more types of polymers selected from the group consisting of polyamide resins, polyimide resins, and polyacrylic resins. These polymers contribute to improving adhesion during lamination and storage modulus.
- the polyamide resin is not particularly limited as long as it is a polymer having an amide structure in its main chain, but from the viewpoint of being used in combination with an epoxy resin, a soluble polyamide is preferable, and more preferably a soluble polyamide having a functional group that can react with an epoxy resin.
- the polyimide resin is not particularly limited as long as it is a polymer having an imide structure in its main chain, but from the viewpoint of use in combination with an epoxy resin, a soluble polyimide is preferable, and a soluble polyimide having a functional group that can react with an epoxy resin is more preferable.
- polyacrylic resins include acrylic ester polymers, methacrylic ester polymers, etc., and preferably those having a functional group capable of reacting with an epoxy resin.
- functional groups that can react with epoxy resins include phenolic hydroxyl groups, amino groups (primary amines and secondary amines), carboxyl groups (including acid anhydrides), cyanate groups, and mercapto groups.
- the total content of two or more types of polymers selected from the group consisting of polyamide resins, polyimide resins, and polyacrylic resins is 16 parts by weight or more and 70 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition.
- the content is preferably 30 parts by weight or more and 68 parts by weight or less, still more preferably 33 parts by weight or more and 45 parts by weight or less, particularly preferably 35 parts by weight or more and 42 parts by weight or less.
- At least one of these two or more types of polymers is a polyamide resin and at least another one is a polyimide resin.
- the two or more types of polymers include at least a polyamide resin and a polyimide resin, a wide temperature range in which lamination is possible can be ensured.
- At least one type is a polymer with a weight average molecular weight of 50,000 or more, and at least another type has a weight average molecular weight of less than 50,000. It is a polymer of In this way, when the above two or more types of polymers include a polymer having a weight average molecular weight of 50,000 or more, the brittleness of the resin composition after curing can be improved, but there is a possibility that the lamination properties and adhesive strength are reduced. .
- the storage modulus of the cured resin composition may be lowered. That is, when the two or more types of polymers include a polymer with a weight average molecular weight of 50,000 or more and a polymer with a weight average molecular weight of less than 50,000, the physical properties of the resin composition can be adjusted, particularly the lamination properties and adhesion. Strength can be improved.
- the resin composition contains a polymer having a weight average molecular weight of less than 50,000 in a proportion of 15 parts by weight or more and 70 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition. It is preferably contained in a proportion of 20 parts by weight or more and 60 parts by weight or less, still more preferably 20 parts by weight or more and 50 parts by weight or less, particularly preferably 20 parts by weight or more and 40 parts by weight or less.
- the resin composition preferably contains a polymer having a weight average molecular weight of 50,000 or more in a proportion of 1 part by weight or more and 20 parts by weight or less, more preferably 1 part by weight or more, based on 100 parts by weight of the total amount of the resin composition. It is contained in a proportion of 18 parts by weight or less, more preferably 5 parts by weight or more and 18 parts by weight or less, particularly preferably 5 parts by weight or more and 15 parts by weight or less.
- the resin composition of the present invention preferably contains one or more epoxy resins, and at least one of the one or more epoxy resins preferably has a naphthalene skeleton.
- the epoxy resin contributes to improving the lamination properties and the storage modulus of the cured resin composition, and when at least one of the epoxy resins has a naphthalene skeleton, it brings about a higher storage modulus of the cured resin composition.
- the total content of the one or more epoxy resins is preferably 30 parts by weight or more and 70 parts by weight or less, more preferably 35 parts by weight or more and 65 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition. , more preferably 45 parts by weight or more and 65 parts by weight or less, particularly preferably 50 parts by weight or more and 63 parts by weight or less.
- Examples of epoxy resins having a naphthalene skeleton are not particularly limited as long as they have a naphthalene skeleton, but the following formula: Examples include compounds represented by: Commercially available examples of epoxy resins having a naphthalene skeleton include HP4710, HP4770, HP4032D, HP5000 and HP6000 manufactured by DIC Corporation, and NC7000H and NC7300L manufactured by Nippon Kayaku Co., Ltd. Preferably, it is a binaphthyl type epoxy resin. .
- the resin composition preferably contains an epoxy resin having a naphthalene skeleton in a proportion of 30 parts by weight or more and 70 parts by weight or less, more preferably 40 parts by weight or more and 70 parts by weight, based on 100 parts by weight of the total amount of the resin composition.
- the content is more preferably 50 parts by weight or more and 70 parts by weight or less, particularly preferably 55 parts by weight or more and 65 parts by weight or less.
- the one or more epoxy resins include two or more epoxy resins, at least one of which is an epoxy resin with a functional group number of 3 or more, and at least one other is an epoxy resin with a functional group number of 3 or more.
- the epoxy resin has less than 3 functional groups.
- at least one type is an epoxy resin in which the number of functional groups in the epoxy group per molecule is 3 or more
- at least another type is an epoxy resin in which the number of functional groups in the epoxy group per molecule is 3 or more.
- the epoxy resin is less than 3.
- the number of functional groups means the average number of functional groups per molecule existing in the resin.
- the number of repeating units (generally represented by n) uniform for all molecules during manufacturing. This is difficult, as molecules with different numbers of repeating units may coexist. In that case, molecules with different numbers of functional groups may coexist, so the sum of the number of functional groups x the abundance ratio (i.e., the value obtained by averaging the number of functional groups by the abundance ratio, and the total abundance ratio is 1) is used as the number of functional groups of the resin. For example, when the abundance ratio of molecules with 2 functional groups in a resin is 0.5 and the abundance ratio of molecules with 3 functional groups in a resin is 0.5, the number of functional groups in the resin is 2 ⁇ 0.
- the heat resistance of the cured resin composition can be improved, but the cured resin composition may become brittle.
- the brittleness of the cured resin composition can be improved by including an epoxy resin having less than 3 functional groups, the heat resistance of the cured resin composition may be reduced. That is, when the epoxy resin contains an epoxy resin with a functional group number of 3 or more and an epoxy resin with a functional group number of less than 3, the physical properties of the resin composition can be adjusted, and in particular, the heat resistance of the resin composition after curing can be adjusted. It is possible to improve brittleness while ensuring strength.
- the epoxy resin having a functional group number of 3 or more is a monomer, it preferably has a functional group number of 3 or more and 4 or less. Further, when the epoxy resin has a large number of functional groups in the main chain such as a novolak type, it is preferable that the number of functional groups is 3 or more and the functional group equivalent is 100 g/eq or more and 400 g/eq or less.
- epoxy resins include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol E epoxy resin, cresol novolac epoxy resin, phenol novolac epoxy resin, alkyl epoxy resin, glycidylamine epoxy resin, and glycidyl ester.
- epoxy resin phenol aralkyl type epoxy resin, trisphenol type epoxy resin, tetraphenylethane type epoxy resin, biphenyl type epoxy resin, bisphenol fluorene type epoxy resin, triazine type epoxy resin, isocyanurate type epoxy resin, alicyclic epoxy resin , heterocyclic epoxy resin, naphthol aralkyl epoxy resin, naphthol novolac epoxy resin, naphthol-phenol cocondensed novolac epoxy resin, naphthol-cresol cocondensed novolak epoxy resin, naphthalene epoxy resin, naphthylene ether epoxy resin , binaphthyl type epoxy resin, anthracene type epoxy resin, etc., and these epoxy resins having an epoxy functional group number of 3 or more and less than 3 can be used in combination.
- the content of the epoxy resin having a functional group number of 3 or more is preferably 15 parts by weight or more and 70 parts by weight or less, more preferably 20 parts by weight or more and 50 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition. More preferably, it is 25 parts by weight or more and 45 parts by weight or less, particularly preferably 30 parts by weight or more and 40 parts by weight or less.
- the content of the epoxy resin having a functional group number of less than 3 is preferably 10 parts by weight or more and 65 parts by weight or less, more preferably 12 parts by weight or more and 50 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition. More preferably, it is 14 parts by weight or more and 40 parts by weight or less, particularly preferably 16 parts by weight or more and 30 parts by weight or less.
- the resin composition of the present invention contains a curing agent.
- the curing agent contributes to promoting the crosslinking reaction between the two or more types of polymers and one or more types of epoxy resin, and to the reaction between the epoxy resins.
- the curing agent is not particularly limited as long as it can promote the reaction of epoxy, but preferred examples include imidazole curing agents, phosphorus curing agents, and the like.
- the content of the curing agent is preferably 0.3 parts by weight or more and 10 parts by weight or less, more preferably 1.0 parts by weight or more and 5.0 parts by weight or less, based on 100 parts by weight of the total amount of the resin composition. , more preferably 2.0 parts by weight or more and 4.0 parts by weight or less.
- Resin-coated copper foil The resin composition of the present invention is preferably used as a resin layer of a resin-coated copper foil.
- a resin layer having a smooth surface having an aspect ratio Str of surface properties measured in accordance with ISO 25178 of 0.3 or more and 1 or less is provided on the smooth surface.
- a resin-coated copper foil comprising a resin layer made of a material.
- the resin composition is in the form of a resin layer, and the resin composition is coated on copper foil (copper layer) using a bar coater so that the thickness of the resin layer after drying becomes a predetermined value. Coat and dry to obtain resin-coated copper foil.
- the coating method is arbitrary, it can be coated using a doctor blade, a bar coater, etc., and a gravure coating method, a die coating method, a knife coating method, etc. can also be adopted.
- the copper foil may be an electrolytic foil or a rolled metal foil (so-called raw foil), or it may be in the form of a surface-treated foil that has been surface-treated on at least one side.
- Surface treatment is a variety of surface treatments performed to improve or impart certain properties to the surface of metal foil (for example, rust prevention, moisture resistance, chemical resistance, acid resistance, heat resistance, and adhesion to a substrate). It can be.
- the surface treatment may be performed on at least one side of the metal foil, or may be performed on both sides of the metal foil. Examples of surface treatments performed on copper foil include rust prevention treatment, silane treatment, roughening treatment, barrier formation treatment, and the like.
- the copper layer has a smooth surface from the viewpoint of circuit downsizing.
- the aspect ratio Str of the surface texture is used as an index for determining the smoothness of the surface of the copper layer.
- the aspect ratio Str of the surface texture is an index indicating the anisotropy of the surface height (presence or absence of a portion where there is a sudden change). The closer Str is to 0, the more anisotropy there is, and the closer Str is to 1, the less anisotropy there is.
- the Str of the surface of the copper layer be close to 1 (no anisotropy).
- the aspect ratio Str of the surface texture of the copper layer is preferably 0.3 or more and 1 or less, more preferably 0.4 or more and 1 or less, still more preferably 0.5 or more and 1 or less, and particularly preferably is 0.6 or more and 1 or less.
- the maximum height Sz of the surface of the copper layer on the side in contact with the resin layer is preferably 6.8 ⁇ m or less, more preferably 0.15 ⁇ m or more and 6.8 ⁇ m or less, and even more preferably 0.25 ⁇ m or more and 5.0 ⁇ m or less. , particularly preferably 0.3 ⁇ m or more and 3.0 ⁇ m or less. Within this range, the resin layer can follow suitably and ensure sufficient adhesion between the copper layer and the glass substrate.
- the "maximum height Sz" is a parameter representing the distance from the highest point to the lowest point on the surface, measured in accordance with ISO25178.
- the maximum peak height Sp on the surface of the copper layer in contact with the resin layer is preferably 3.3 ⁇ m or less, more preferably 0.06 ⁇ m or more and 3.1 ⁇ m or less, and even more preferably 0.06 ⁇ m or more and 3.0 ⁇ m or less. , particularly preferably from 0.07 ⁇ m to 2.9 ⁇ m.
- the resin layer can follow suitably and ensure sufficient adhesion between the copper layer and the glass substrate.
- the "maximum peak height Sp" is a three-dimensional parameter representing the maximum value of the height from the average plane of the surface, measured in accordance with ISO25178.
- the root mean square gradient Sdq on the surface of the copper layer in contact with the resin layer is preferably 0.01 or more and 2.3 or less, more preferably 0.02 or more and 2.0 or less, and even more preferably 0.04 or more and 1. 8 or less. Within this range, the resin layer can follow suitably and ensure sufficient adhesion between the copper layer and the glass substrate.
- the "root mean square slope Sdq" is a parameter calculated based on the root mean square of the slope at all points in the defined area, which is measured in accordance with ISO25178. In other words, since it is a three-dimensional parameter that evaluates the magnitude of the local inclination angle, it is possible to quantify the steepness of the surface unevenness. For example, the Sdq of a completely flat surface is 0, and the Sdq increases if the surface is sloped. Sdq of a plane consisting of a 45 degree tilt component is 1.
- Str, Sz, Sp, and Sdq can be measured using a commercially available laser microscope (for example, OLS5000 manufactured by Olympus Corporation) in accordance with ISO 25178 and according to the procedures shown in Examples.
- a commercially available laser microscope for example, OLS5000 manufactured by Olympus Corporation
- the thickness of the copper layer is preferably 5 ⁇ m or less, more preferably 0.5 ⁇ m or more and 4 ⁇ m or less, even more preferably 1 ⁇ m or more and 4 ⁇ m or less, particularly preferably 1 ⁇ m or more and 3 ⁇ m or less. With such a thickness, circuit narrowing such as undercut can be reduced when cutting a fine pattern circuit.
- a resin-coated copper foil in which the copper layer has a thickness of 5 ⁇ m or less and further includes a carrier layer on the surface opposite to the smooth surface of the copper layer.
- Ru a carrier layer on the surface opposite to the smooth surface of the copper layer.
- copper can be further formed to a desired thickness on the copper layer, typically using a known method such as copper plating.
- the thickness of the resin layer is not particularly limited, but is preferably 1 ⁇ m or more and 10 ⁇ m or less, more preferably 2 ⁇ m or more and 8 ⁇ m or less, even more preferably 2 ⁇ m or more and 7 ⁇ m or less, and particularly preferably 3 ⁇ m or more and 7 ⁇ m or less. With such a thickness, the above-described characteristics of the present invention can be more effectively realized, and the resin layer can be easily formed by applying the resin composition. It also improves handling.
- the resin composition of the present invention is preferably used as a resin layer of a composite material comprising a glass substrate and resin-coated copper foil. That is, according to a preferred embodiment of the present invention, a composite material is provided that includes a glass substrate and a resin-coated copper foil provided on at least one surface of the glass substrate such that the resin layer is in contact with the glass substrate. .
- a composite material is provided that includes a glass substrate and a resin-coated copper foil provided on at least one surface of the glass substrate such that the resin layer is in contact with the glass substrate.
- the laminating method has the above-mentioned advantages, it is difficult to increase the pressure in the pressing process, and it is difficult to ensure adhesiveness between the copper foil and the glass substrate. Therefore, by using the resin composition of the present invention as a resin layer, a copper foil and a glass substrate can be bonded together by a lamination method, and a composite material can be efficiently produced.
- Examples 1 to 11 (1) Preparation of varnish First, the resin components shown below were prepared as raw material components for varnish.
- (a1) Polyimide resin with a molecular weight of less than 50,000: - Polyimide A manufactured by JFE Chemical Corporation (weight average molecular weight less than 50,000) - Polyimide B manufactured by JFE Chemical Corporation (weight average molecular weight less than 50,000) - PIAD300 (manufactured by Arakawa Chemical Industry Co., Ltd., medium molecular weight thermoplastic polyimide, weight average molecular weight less than 50,000)
- (a2) Polyamide resin with a molecular weight of 50,000 or more: - DAN1 (manufactured by Nippon Kayaku Co., Ltd., weight average molecular weight 50,000 or more)
- (a3) Acrylic resin with a molecular weight of 50,000 or more: - SG-P3 (manufactured by Nagase ChemteX Corporation, functional group: epoxy, weight average molecular weight
- Each raw material component and organic solvent were weighed and placed in a flask so as to have the blending ratio (parts by weight) and solid content concentration (% by weight) shown in Tables 1 and 2.
- the flask was heated to 60° C. with a mantle heater and stirred with a stirring blade to dissolve each raw material component in the solvent, and then cooled to room temperature to obtain a varnish.
- DAN1 polyamide resin
- DAN1 was added to the cyclopentanone solvent in advance to prepare a solution with a solid content concentration of 20%.
- This solution was added to a separately prepared solution in which other components were dissolved and cooled to room temperature so as to have the blending ratio (parts by weight) of DAN1 shown in Tables 1 and 2, and the mixture was stirred to obtain a varnish.
- the surface profile of an area of 16,384 ⁇ m 2 on the smooth surface of the copper foil was measured using the laser microscope described above using an objective lens with a magnification of 100 times, under the conditions of the scanning mode "3D standard + color” and the shooting mode "Auto". It was measured.
- spike noise was removed by noise removal and tilt removal was automatically performed, and then the aspect ratio Str of the surface texture was measured by surface texture analysis.
- the shape was removed by F calculation ("multidimensional curve 3rd order" was selected), and the cutoff wavelength by the S filter was set to 0.55 ⁇ m, and the cutoff wavelength by the L filter was set to 10 ⁇ m.
- the measurements of Str, Sz, Sp, and Sdq were carried out in eight different fields of view, and the average values of Str, Sz, Sp, and Sdq in all the fields of view were adopted as the values of the smooth surface of the sample.
- the diluted varnish obtained in (2) above was applied to the smooth surface of the copper foil using a bar coater, and the mixture was placed in an oven preheated to 150°C and dried by heating for 2 minutes to obtain a resin-coated copper foil. Ta. At this time, coating conditions were adjusted so that the thickness of the resin layer after drying was 5 ⁇ m.
- ⁇ Storage modulus> A strip-shaped sample of 5 mm x 50 mm was cut out from the resin film obtained in (3) above, and DMA measurement was performed using a DMA (dynamic viscoelasticity measurement) device (manufactured by Hitachi High-Tech Science, DMA7100). This measurement was carried out in accordance with JIS K 7244-4:1999 by placing a resin specimen with a width of 5.0 mm and a thickness of 100 ⁇ m in a clamp with a clamp distance of 20.0 mm, and heating the resin at 30°C in an atmospheric atmosphere. The measurement was performed at a measurement frequency of 1 Hz by heating from 280° C. to 280° C. at a temperature increase rate of 5° C./min.
- DMA dynamic viscoelasticity measurement
- ⁇ Adhesive strength> The composite material obtained in (6) above was plated with copper, and a copper wiring with a wiring width of 10 mm and a wiring thickness of 20 ⁇ m was formed by a subtractive method, and the adhesive strength (peel strength) was measured in accordance with JIS C 6481. . The measurement was carried out five times, and the average value was taken as the value of adhesive strength, which was evaluated according to the following criteria.
- the adhesive strength measured here is a value that reflects three failure modes: interfacial peeling between glass/resin, cohesive failure within resin, and interfacial peeling between resin/copper foil. The higher the value, the better the adhesion to glass, the strength of the resin layer, and the adhesion to low-roughness foil.
- ⁇ Warp> The amount of warpage of the substrate of the composite material obtained in (6) above was measured using a 3D heating surface shape measuring device (Thermoray PS200S, manufactured by Akrometrix). The amount of warpage was calculated from the difference between the maximum and minimum Z coordinate values of the glass laminate. The measurement was carried out five times in an atmosphere of 27°C, and the average value of the obtained measured values was taken as the warpage, and the evaluation was made according to the following criteria. The results were as shown in Tables 3 and 4. -Evaluation A: The amount of warpage is less than 500 ⁇ m -Evaluation C: The amount of warpage is 500 ⁇ m or more
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Abstract
L'invention concerne une composition de résine dotée d'une résistance exceptionnelle à la chaleur et permettant la liaison d'une feuille de cuivre et d'un substrat de verre par la mise en œuvre d'un procédé de stratification. La composition de résine selon l'invention contient : au moins deux polymères sélectionnés dans le groupe constitué par les résines de polyamide, les résines de polyimide et les résines polyacryliques ; au moins une résine époxy ; et un agent de durcissement. Parmi les deux polymères au moins, au moins un polymère est doté d'une masse moléculaire moyenne en poids de 50 000 ou supérieure, et au moins un autre polymère est doté d'une masse moléculaire moyenne en poids inférieure à 50 000.
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH05179220A (ja) * | 1991-12-26 | 1993-07-20 | Ube Ind Ltd | 耐熱性の接着剤 |
JP2003292575A (ja) * | 2002-01-31 | 2003-10-15 | Dainippon Ink & Chem Inc | 熱硬化性ポリイミド樹脂組成物、ポリイミド樹脂の製造方法およびポリイミド樹脂 |
JP2004333672A (ja) * | 2003-05-02 | 2004-11-25 | Kanegafuchi Chem Ind Co Ltd | 貯蔵安定性の良い感光性樹脂組成物及び感光性ドライフィルムレジスト、並びにその利用 |
WO2007004569A1 (fr) * | 2005-07-05 | 2007-01-11 | Hitachi Chemical Company, Ltd. | Composition adhésive photosensible et film adhésif, feuille adhésive, tranche de semi-conducteur avec couche adhésive, dispositif semi-conducteur et pièce électronique obtenus en utilisant cette composition |
JP2012241134A (ja) * | 2011-05-20 | 2012-12-10 | Hitachi Chemical Co Ltd | 接着剤組成物、接着シート及び半導体装置 |
JP2018172533A (ja) * | 2017-03-31 | 2018-11-08 | 太陽インキ製造株式会社 | 硬化性樹脂組成物、積層構造体、その硬化物、および電子部品 |
WO2020195661A1 (fr) * | 2019-03-28 | 2020-10-01 | 三井金属鉱業株式会社 | Composition de résine et feuille de cuivre à laquelle une résine est fixée |
-
2023
- 2023-03-07 WO PCT/JP2023/008657 patent/WO2023189298A1/fr unknown
- 2023-03-22 TW TW112110595A patent/TW202342575A/zh unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05179220A (ja) * | 1991-12-26 | 1993-07-20 | Ube Ind Ltd | 耐熱性の接着剤 |
JP2003292575A (ja) * | 2002-01-31 | 2003-10-15 | Dainippon Ink & Chem Inc | 熱硬化性ポリイミド樹脂組成物、ポリイミド樹脂の製造方法およびポリイミド樹脂 |
JP2004333672A (ja) * | 2003-05-02 | 2004-11-25 | Kanegafuchi Chem Ind Co Ltd | 貯蔵安定性の良い感光性樹脂組成物及び感光性ドライフィルムレジスト、並びにその利用 |
WO2007004569A1 (fr) * | 2005-07-05 | 2007-01-11 | Hitachi Chemical Company, Ltd. | Composition adhésive photosensible et film adhésif, feuille adhésive, tranche de semi-conducteur avec couche adhésive, dispositif semi-conducteur et pièce électronique obtenus en utilisant cette composition |
JP2012241134A (ja) * | 2011-05-20 | 2012-12-10 | Hitachi Chemical Co Ltd | 接着剤組成物、接着シート及び半導体装置 |
JP2018172533A (ja) * | 2017-03-31 | 2018-11-08 | 太陽インキ製造株式会社 | 硬化性樹脂組成物、積層構造体、その硬化物、および電子部品 |
WO2020195661A1 (fr) * | 2019-03-28 | 2020-10-01 | 三井金属鉱業株式会社 | Composition de résine et feuille de cuivre à laquelle une résine est fixée |
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