WO2019150433A1 - Composition de résine thermodurcissable, adhésif sous forme de film, feuille adhésive, et procédé de production de dispositif à semi-conducteur - Google Patents
Composition de résine thermodurcissable, adhésif sous forme de film, feuille adhésive, et procédé de production de dispositif à semi-conducteur Download PDFInfo
- Publication number
- WO2019150433A1 WO2019150433A1 PCT/JP2018/002982 JP2018002982W WO2019150433A1 WO 2019150433 A1 WO2019150433 A1 WO 2019150433A1 JP 2018002982 W JP2018002982 W JP 2018002982W WO 2019150433 A1 WO2019150433 A1 WO 2019150433A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- film
- adhesive
- resin composition
- component
- thermosetting resin
- Prior art date
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- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 43
- 239000011342 resin composition Substances 0.000 title claims abstract description 42
- 239000000853 adhesive Substances 0.000 title claims description 140
- 230000001070 adhesive effect Effects 0.000 title claims description 140
- 239000004065 semiconductor Substances 0.000 title claims description 121
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 239000003822 epoxy resin Substances 0.000 claims abstract description 34
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
- 229920001971 elastomer Polymers 0.000 claims abstract description 25
- 239000000806 elastomer Substances 0.000 claims abstract description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
- 125000000524 functional group Chemical group 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 229920000178 Acrylic resin Polymers 0.000 claims description 20
- 239000004925 Acrylic resin Substances 0.000 claims description 20
- 239000005011 phenolic resin Substances 0.000 claims description 15
- 238000010030 laminating Methods 0.000 claims description 10
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 230000001681 protective effect Effects 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 238000002788 crimping Methods 0.000 claims 1
- 238000011156 evaluation Methods 0.000 description 15
- 239000002966 varnish Substances 0.000 description 15
- 238000011282 treatment Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- -1 ester compound Chemical class 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 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 8
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 230000009477 glass transition Effects 0.000 description 6
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- 239000000523 sample Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011800 void material Substances 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
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- 235000010290 biphenyl Nutrition 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
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- 125000003700 epoxy group Chemical group 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 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 description 2
- 238000005304 joining Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- 235000019792 magnesium silicate Nutrition 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
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- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- BLBVJHVRECUXKP-UHFFFAOYSA-N 2,3-dimethoxy-1,4-dimethylbenzene Chemical group COC1=C(C)C=CC(C)=C1OC BLBVJHVRECUXKP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
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- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- 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
- C08G59/40—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 curing agents used
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- C08G59/621—Phenols
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
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- C—CHEMISTRY; METALLURGY
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C—CHEMISTRY; METALLURGY
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C09J11/08—Macromolecular additives
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- C—CHEMISTRY; METALLURGY
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
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- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
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- H01L25/04—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers
- H01L25/065—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers the devices being of a type provided for in group H01L27/00
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- H01L25/04—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers
- H01L25/07—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers the devices being of a type provided for in group H01L29/00
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- H01L25/18—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof the devices being of types provided for in two or more different subgroups of the same main group of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N
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- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/4805—Shape
- H01L2224/4809—Loop shape
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/484—Connecting portions
- H01L2224/4847—Connecting portions the connecting portion on the bonding area of the semiconductor or solid-state body being a wedge bond
- H01L2224/48472—Connecting portions the connecting portion on the bonding area of the semiconductor or solid-state body being a wedge bond the other connecting portion not on the bonding area also being a wedge bond, i.e. wedge-to-wedge
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- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
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- H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
- H01L2224/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
- H01L2224/8319—Arrangement of the layer connectors prior to mounting
- H01L2224/83191—Arrangement of the layer connectors prior to mounting wherein the layer connectors are disposed only on the semiconductor or solid-state body
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- H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
- H01L2224/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
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- H01L2224/92—Specific sequence of method steps
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- H01L2924/181—Encapsulation
Definitions
- the present invention relates to a thermosetting resin composition, a film adhesive, an adhesive sheet, and a method for manufacturing a semiconductor device.
- silver paste is mainly used for joining a semiconductor chip and a support member for mounting the semiconductor chip.
- the supporting members used are also required to be miniaturized and densified.
- problems such as occurrence of defects during wire bonding due to protrusion of the paste or inclination of the semiconductor chip, difficulty in controlling the film thickness, and generation of voids may occur.
- a film adhesive for joining a semiconductor chip and a support member has been used (see, for example, Patent Document 1).
- an adhesive sheet comprising a dicing tape and a film adhesive laminated on the dicing tape
- the film adhesive is attached to the back surface of the semiconductor wafer, and the semiconductor wafer is separated into pieces by dicing.
- a semiconductor chip with an adhesive can be obtained.
- the obtained semiconductor chip with a film adhesive can be attached to a support member via a film adhesive and bonded by thermocompression bonding.
- the film-like adhesive is used as FOW (Film Over Wire) which is a wire-embedded film-like adhesive or FOD (Film Over Die) which is a semiconductor chip-embedded film-like adhesive
- FOW Flexible Over Wire
- FOD Fin Off Die
- high fluidity is required at the time of thermocompression bonding. Therefore, the frequency and amount of bleed tend to increase further. In some cases, the bleed may occur even on the upper surface of the semiconductor chip, which may lead to electrical failure or wire bonding failure.
- the present invention has been made in view of such circumstances, and is a thermosetting resin capable of suppressing an increase in the amount of bleed during high-temperature pressure treatment while having good embedding properties during thermocompression bonding.
- the main purpose is to provide a composition.
- One aspect of the present invention is an epoxy resin, a curing agent, a first elastomer having at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group, and a second elastomer having no carboxy group and a hydroxyl group.
- a thermosetting resin composition comprising: According to such a thermosetting resin composition, it is possible to suppress an increase in the amount of bleed during high-temperature pressure treatment while having good embedding properties during thermocompression bonding.
- the curing agent may contain a phenol resin.
- the first elastomer may be an acrylic resin having at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group.
- the second elastomer may be an acrylic resin having no carboxy group and no hydroxyl group.
- the epoxy resin may contain an epoxy resin that is liquid at 25 ° C.
- thermosetting resin composition may further contain an inorganic filler. Moreover, the thermosetting resin composition may further contain a curing accelerator.
- thermosetting resin composition is a semiconductor in which a first semiconductor element is wire-bonded to a substrate via a first wire, and a second semiconductor element is pressure-bonded on the first semiconductor element.
- the second semiconductor element may be crimped and used to embed at least a part of the first wire.
- the present invention further includes an epoxy resin, a curing agent, a first elastomer having at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group, and a second elastomer having no carboxy group and a hydroxyl group,
- the thermosetting resin composition containing the first semiconductor element is wire bonded to the substrate via the first wire, and the second semiconductor element is pressure-bonded on the first semiconductor element.
- the second semiconductor element may be crimped and at least a part of the first wire may be embedded and applied as an adhesive or an adhesive manufacturing.
- the present invention provides a film adhesive formed by forming the above-mentioned thermosetting resin composition into a film.
- the present invention provides an adhesive sheet comprising a base material and the above-described film adhesive provided on the base material.
- the substrate may be a dicing tape.
- an adhesive sheet whose base material is a dicing tape may be referred to as a “dicing die bonding integrated adhesive sheet”.
- the adhesive sheet may further include a protective film laminated on the surface opposite to the base of the film adhesive.
- the present invention provides a wire bonding step of electrically connecting a first semiconductor element via a first wire on a substrate, and the above-described film shape on one side of the second semiconductor element.
- a wire bonding step of electrically connecting a first semiconductor element via a first wire on a substrate, and the above-described film shape on one side of the second semiconductor element.
- the first semiconductor chip is wire bonded to the semiconductor substrate via the first wire, and the second semiconductor chip is pressure-bonded to the first semiconductor chip via the adhesive film.
- the first semiconductor chip may be a wire embedded type semiconductor device in which at least a part of the first wire is embedded in the adhesive film, and the first wire and the first semiconductor chip are embedded in the adhesive film. It may be a chip embedded semiconductor device.
- thermosetting resin composition capable of suppressing an increase in the amount of bleed during high-temperature pressure treatment while having good embedding properties during thermocompression bonding. Therefore, the film-like adhesive formed by forming the thermosetting resin composition into a film is FOD (Film Over Die) which is a semiconductor chip-embedded film-like adhesive or FOW which is a wire-embedded film-like adhesive. (Film Over Wire) may be useful. Moreover, according to this invention, the manufacturing method of the adhesive sheet using such a film adhesive and a semiconductor device is provided.
- FIG. 1 is a schematic cross-sectional view showing a semiconductor device according to an embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of
- (meth) acrylic acid means acrylic acid or methacrylic acid corresponding thereto.
- thermosetting resin composition is a first resin having at least one functional group selected from the group consisting of (A) an epoxy resin, (B) a curing agent, and (C) a carboxy group and a hydroxyl group. And (D) a second elastomer having no carboxy group and no hydroxyl group.
- the thermosetting resin composition can be in a completely cured product (C stage) state after the curing process through a semi-cured (B stage) state.
- the component (A) can be used without particular limitation as long as it has an epoxy group in the molecule.
- the component (A) for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F novolak type Epoxy resin, dicyclopentadiene skeleton-containing epoxy resin, stilbene-type epoxy resin, triazine skeleton-containing epoxy resin, fluorene skeleton-containing epoxy resin, triphenolphenolmethane-type epoxy resin, biphenyl-type epoxy resin, xylylene-type epoxy resin, phenylaralkyl-type epoxy Diglycidies of polycyclic aromatics such as resins, biphenyl aralkyl type epoxy resins, naphthalene type epoxy resins, polyfunctional phenols and anthracene And ether compounds.
- the component (A) preferably has a 150 ° C. melt viscosity of 1.0 Pa ⁇ s or less from the viewpoint of fluidity.
- the epoxy resin may contain the epoxy resin which is liquid at 25 degreeC.
- the epoxy equivalent of the component (A) is not particularly limited, but may be 90 to 300 g / eq, 110 to 290 g / eq, or 110 to 290 g / eq. When the epoxy equivalent of the component (A) is in such a range, the fluidity tends to be secured while maintaining the bulk strength of the film adhesive.
- Examples of commercially available components (A) include HP-7200 series manufactured by DIC Corporation, YDCN series manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., NC-3000 series and NC-7000 series manufactured by Nippon Kayaku Co., Ltd., and the like. It is done.
- (B) There is no restriction
- a component a phenol resin, an ester compound, an aromatic amine, an aliphatic amine, an acid anhydride etc. are mentioned, for example. You may use these individually by 1 type or in combination of 2 or more types. Among these, from the viewpoint of reactivity and stability over time, the component (B) may contain a phenol resin.
- the phenol resin can be used without particular limitation as long as it has a phenolic hydroxyl group in the molecule.
- examples of the phenol resin include phenols such as phenol, cresol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol, and / or naphthols such as ⁇ -naphthol, ⁇ -naphthol, dihydroxynaphthalene, and formaldehyde.
- a novolak-type phenol resin obtained by condensation or co-condensation with a compound having an aldehyde group in the presence of an acidic catalyst phenols such as allylated bisphenol A, allylated bisphenol F, allylated naphthalenediol, phenol novolak, phenol, and / or Or phenol aralkyl resins, naphthol aralkyl resins, biphenyl aralkyl type resins synthesized from naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl Examples thereof include an enol resin and a phenylaralkyl type phenol resin.
- the phenol resin has a water absorption of 2% by mass or less in a constant temperature and humidity chamber of 85 ° C. and 85% RH for 48 hours, and a thermogravimetric analyzer (TGA). It is preferable that the heating mass decrease rate (heating rate: 5 ° C./min, atmosphere: nitrogen) at 350 ° C. measured in step 1 is less than 5% by mass.
- phenol resins examples include Phenolite KA series, TD series (manufactured by DIC Corporation), Millex XLC series, XL series (manufactured by Mitsui Chemicals), and HE series (manufactured by Air Water Corporation). Can be mentioned.
- the hydroxyl equivalent of the phenol resin is not particularly limited, but may be 80 to 250 g / eq, 90 to 200 g / eq, or 100 to 180 g / eq.
- the adhesive strength tends to be maintained higher while maintaining the fluidity of the film adhesive.
- the ratio of the epoxy equivalent of component (A) to the hydroxyl equivalent of component (B) is 0.30 / 0.70 to 0.70 from the viewpoint of curability. /0.30, 0.35 / 0.65 to 0.65 / 0.35, 0.40 / 0.60 to 0.60 / 0.40, or 0.45 / 0.55 to 0.55 / It may be 0.45.
- the equivalent ratio is 0.30 / 0.70 or more, more sufficient curability tends to be obtained.
- the equivalent ratio is 0.70 / 0.30 or less, the viscosity can be prevented from becoming too high, and more sufficient fluidity can be obtained.
- the total content of the component (A) and the component (B) may be 10 to 80% by mass based on the total amount of the thermosetting resin composition.
- the total content of the component (A) and the component (B) may be 20% by mass or more, 25% by mass or more, or 30% by mass or more, and is 70% by mass or less, 60% by mass or less, or 50% by mass. % Or less.
- the total content of the component (A) and the component (B) is 10% by mass or more based on the total amount of the thermosetting resin composition, sufficient adhesive force tends to be obtained.
- the viscosity can be prevented from becoming too low, and the amount of bleed can be reduced. There is a tendency to be able to suppress more.
- Component (C) is an elastomer having at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group.
- the component (C) preferably has a glass transition temperature (Tg) of the polymer constituting the elastomer of 50 ° C. or lower.
- the component (C) is not particularly limited as long as it has at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group.
- an acrylic resin, a polyester resin, a polyamide resin, a polyimide resin, a silicone resin examples thereof include butadiene resins, acrylonitrile resins, and modified products thereof having at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group.
- the component (C) may be an acrylic resin having at least one functional group selected from the group consisting of a carboxy group and a hydroxyl group from the viewpoint of solubility in a solvent and fluidity.
- the acrylic resin means a polymer containing a structural unit derived from a (meth) acrylic acid ester.
- the acrylic resin is preferably a polymer including a structural unit derived from a (meth) acrylic acid ester having an alcoholic or phenolic hydroxyl group or a carboxy group as a structural unit.
- the acrylic resin may be an acrylic rubber such as a copolymer of (meth) acrylic acid ester and acrylonitrile.
- the glass transition temperature (Tg) of the component (C) may be ⁇ 50 to 50 ° C. or ⁇ 30 to 30 ° C. If the Tg of the acrylic resin is ⁇ 50 ° C. or higher, the thermosetting resin composition tends to be prevented from becoming too flexible. Thereby, it becomes easy to cut
- the glass transition temperature (Tg) means a value measured using a DSC (thermal differential scanning calorimeter) (for example, “Thermo Plus 2” manufactured by Rigaku Corporation).
- the weight average molecular weight (Mw) of the component (C) may be 100,000 to 3 million or 500,000 to 2 million.
- Mw means a value measured by gel permeation chromatography (GPC) and converted using a standard polystyrene calibration curve.
- the acid value of the component (C) having a carboxy group may be 1 to 60 mgKOH / g, 3 to 50 mgKOH / g, or 5 to 40 mgKOH / g from the viewpoint of curability.
- the acid value is in such a range, gelation in the varnish and a decrease in fluidity in the B stage state tend to be prevented.
- the hydroxyl value of the component (C) having a hydroxyl group may be 1 to 60 mgKOH / g, 3 to 50 mgKOH / g, or 5 to 40 mgKOH / g from the viewpoint of curability.
- the hydroxyl value is in such a range, gelation in the varnish and a decrease in fluidity in the B stage state tend to be prevented.
- Examples of the commercially available component (C) include SG-70L, SG-708-6, WS-023 EK30, SG-280 EK23 (all manufactured by Nagase ChemteX Corporation).
- Component (D) is an elastomer having no carboxy group and no hydroxyl group.
- the component (D) preferably has a glass transition temperature (Tg) of the polymer constituting the elastomer of 50 ° C. or lower.
- the component (D) is not particularly limited as long as it does not have a carboxy group and a hydroxyl group, and examples thereof include acrylic resins, polyester resins, polyamide resins, polyimide resins, silicone resins, butadiene resins, acrylonitrile resins, and modified products thereof. And what does not have a carboxy group and a hydroxyl group is mentioned.
- the component (D) may be an acrylic resin having no carboxy group and no hydroxyl group from the viewpoint of solubility in a solvent and fluidity.
- the acrylic resin has the same meaning as described above.
- the acrylic resin is preferably a polymer containing a functional monomer (such as (meth) acrylic acid ester) having an epoxy group such as a glycidyl group as a structural unit.
- the acrylic resin may be an acrylic rubber such as a copolymer of (meth) acrylic acid ester and acrylonitrile.
- the glass transition temperature (Tg) of the component (D) may be ⁇ 50 to 50 ° C. or ⁇ 30 to 30 ° C. If the Tg of the acrylic resin is ⁇ 50 ° C. or higher, the thermosetting resin composition tends to be prevented from becoming too flexible. Thereby, it becomes easy to cut
- the glass transition temperature (Tg) means a value measured using a DSC (thermal differential scanning calorimeter) (for example, “Thermo Plus 2” manufactured by Rigaku Corporation).
- the weight average molecular weight (Mw) of the component (D) may be 100,000 to 3 million or 500,000 to 2 million.
- Mw means a value measured by gel permeation chromatography (GPC) and converted using a standard polystyrene calibration curve.
- Examples of the commercially available component (D) include SG-P3, SG-80H, and HTR-860P-3CSP (all manufactured by Nagase ChemteX Corporation).
- the total content of the component (C) and the component (D) is 20 to 150 parts by mass, 30 to 100 parts by mass, or 40 to 70 with respect to 100 parts by mass of the total amount of the components (A) and (B). It may be a mass part.
- the total content of the component (C) and the component (D) is 20 parts by mass or more with respect to 100 parts by mass of the total amount of the component (A) and the component (B)
- the film formability tends to be more excellent.
- the total content of the component (C) and the component (D) is 150 parts by mass or less with respect to 100 parts by mass of the total amount of the component (A) and the component (B)
- embedding tends to be more excellent.
- Mass ratio of component (C) to the total amount of component (C) and component (D) in the thermosetting resin composition May be between 0.01 and 0.50.
- the mass ratio may be 0.02 or more, 0.03 or more, or 0.05 or more, and may be 0.30 or less, 0.20 or less, or 0.10 or less.
- the mass ratio of the component (C) to the component (C) and the component (D) is 0.01 or more, the increase in the amount of bleed during the high-temperature pressure treatment tends to be further suppressed.
- the mass ratio of the component (C) to the component (C) and the component (D) is 0.50 or less, better embedding property tends to be maintained.
- thermosetting resin composition according to the present embodiment may further contain (E) an inorganic filler.
- the inorganic filler include aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride, aluminum borate whisker, boron nitride, crystal Examples thereof include crystalline silica and amorphous silica. These may be used individually by 1 type and may be used in combination of 2 or more type.
- the inorganic filler may contain aluminum oxide, aluminum nitride, boron nitride, crystalline silica, or amorphous silica. Further, from the viewpoint of adjusting the melt viscosity of the thermosetting resin composition and from the viewpoint of imparting thixotropic properties to the thermosetting resin composition, the inorganic filler is aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, Calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, crystalline silica or amorphous silica may be included.
- the average particle diameter of the component (E) may be 0.005 to 0.5 ⁇ m or 0.05 to 0.3 ⁇ m from the viewpoint of further improving the adhesiveness.
- an average particle diameter means the value calculated
- the component may be surface-treated with a surface treatment agent from the viewpoint of compatibility between the surface and the solvent, other components, and the like, and adhesive strength.
- a surface treatment agent include a silane coupling agent.
- the functional group of the silane coupling agent include a vinyl group, a (meth) acryloyl group, an epoxy group, a mercapto group, an amino group, a diamino group, an alkoxy group, and an ethoxy group.
- the content of the component (E) is 10 to 90 parts by mass or 10 to 50 parts by mass with respect to 100 parts by mass of the total amount of the components (A), (B), (C), and (D). It may be. Adhesion before hardening that content of (E) component is 10 mass parts or more with respect to 100 mass parts of total amounts of (A) component, (B) component, (C) component, and (D) component The dicing property of the layer is improved, and the adhesive force of the adhesive layer after curing tends to be improved. When the content of the component (E) is 90 parts by mass or less with respect to 100 parts by mass of the total amount of the components (A), (B), (C), and (D), the fluidity is lowered. And the elastic modulus of the cured film adhesive can be prevented from becoming too high.
- thermosetting resin composition according to this embodiment may further contain (F) a curing accelerator.
- a hardening accelerator is not specifically limited, What is generally used can be used.
- the component (F) include imidazoles and derivatives thereof, organic phosphorus compounds, secondary amines, tertiary amines, quaternary ammonium salts, and the like. You may use these individually by 1 type or in combination of 2 or more types. Among these, from the viewpoint of reactivity, the component (F) may be imidazoles and derivatives thereof.
- imidazoles examples include 2-methylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, and the like. You may use these individually by 1 type or in combination of 2 or more types.
- the content of the component (F) is 0.04 to 3 parts by mass or 0.04 to 0.04 to 100 parts by mass of the total amount of the components (A), (B), (C), and (D). It may be 0.2 parts by mass.
- content of (F) component exists in such a range, it exists in the tendency which can make sclerosis
- thermosetting resin composition according to the present embodiment may further contain an antioxidant, a silane coupling agent, a rheology control agent, and the like as other components.
- the content of these components may be 0.02 to 3 parts by mass with respect to 100 parts by mass as the total of components (A), (B), (C), and (D).
- the adhesive composition according to this embodiment may be used as an adhesive varnish diluted with a solvent.
- the solvent is not particularly limited as long as it can dissolve components other than the component (E).
- the solvent include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene and p-cymene; aliphatic hydrocarbons such as hexane and heptane; cyclic alkanes such as methylcyclohexane; tetrahydrofuran, 1,4-dioxane and the like.
- Cyclic ether such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone; ester such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, ⁇ -butyrolactone; Examples thereof include carbonic acid esters such as ethylene carbonate and propylene carbonate; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone. You may use these individually by 1 type or in combination of 2 or more types.
- the solvent may be toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexane from the viewpoints of solubility and boiling point.
- the solid component concentration in the adhesive varnish may be 10 to 80% by mass based on the total mass of the adhesive varnish.
- Adhesive varnish mixes (A) component, (B) component, (C) component, (D) component and solvent, and (E) component, (F) component, and other components as necessary It can be prepared by kneading. Mixing and kneading can be performed by appropriately combining dispersers such as a normal stirrer, a raking machine, a triple roll, a ball mill, and a bead mill.
- the mixing time can be reduced by mixing the component (E) and the low molecular weight component in advance and then blending the high molecular weight component.
- bubbles in the varnish may be removed by vacuum degassing or the like.
- FIG. 1 is a schematic cross-sectional view showing a film adhesive according to an embodiment.
- the film adhesive 10 is formed by forming the above-described adhesive composition into a film.
- the film adhesive 10 may be in a semi-cured (B stage) state.
- Such a film adhesive 10 can be formed by applying an adhesive composition to a support film.
- the film adhesive 10 can be formed by applying the adhesive varnish to a support film and removing the solvent by heating and drying.
- the support film is not particularly limited, and examples thereof include films of polytetrafluoroethylene, polyethylene, polypropylene, polymethylpentene, polyethylene terephthalate, polyimide, and the like.
- the thickness of the support film may be, for example, 60 to 200 ⁇ m or 70 to 170 ⁇ m.
- a known method can be used, for example, knife coating method, roll coating method, spray coating method, gravure coating method, bar coating method, curtain coating method, etc. It is done.
- the conditions for the heat drying are not particularly limited as long as the solvent used is sufficiently volatilized, but may be, for example, 50 to 200 ° C. for 0.1 to 90 minutes.
- the thickness of the film adhesive can be appropriately adjusted according to the application.
- the thickness of the film adhesive may be 20 to 200 ⁇ m, 30 to 200 ⁇ m, or 40 to 150 ⁇ m from the viewpoint of sufficiently embedding irregularities such as a semiconductor chip, a wire, and a wiring circuit of a substrate.
- FIG. 2 is a schematic cross-sectional view showing an adhesive sheet according to an embodiment.
- the adhesive sheet 100 includes a base material 20 and the above-described film adhesive 10 provided on the base material.
- the substrate 20 is not particularly limited, but may be a substrate film.
- the base film may be the same as the above support film.
- the base material 20 may be a dicing tape.
- Such an adhesive sheet can be used as a dicing die bonding integrated adhesive sheet. In this case, since the lamination process to the semiconductor wafer is performed once, the work efficiency can be improved.
- the dicing tape examples include plastic films such as a polytetrafluoroethylene film, a polyethylene terephthalate film, a polyethylene film, a polypropylene film, a polymethylpentene film, and a polyimide film.
- the dicing tape may be subjected to surface treatment such as primer coating, UV treatment, corona discharge treatment, polishing treatment, and etching treatment as necessary.
- the dicing tape is preferably one having adhesiveness.
- Such a dicing tape may be one obtained by imparting adhesiveness to the above-mentioned plastic film, or may be one obtained by providing an adhesive layer on one side of the above-mentioned plastic film.
- the adhesive sheet 100 can be formed by applying an adhesive composition to a base film in the same manner as the above-described method for forming a film adhesive.
- the method for applying the adhesive composition to the substrate 20 may be the same as the method for applying the adhesive composition to the support film.
- the adhesive sheet 100 may be formed using a film adhesive prepared in advance.
- the adhesive sheet 100 can be formed by laminating under a predetermined condition (for example, room temperature (20 ° C.) or a heated state) using a roll laminator, a vacuum laminator, or the like. Since the adhesive sheet 100 can be continuously manufactured and has high efficiency, it is preferably formed using a roll laminator in a heated state.
- the thickness of the film adhesive 10 may be 20 to 200 ⁇ m, 30 to 200 ⁇ m, or 40 to 150 ⁇ m from the viewpoint of embedding properties such as unevenness of a semiconductor chip, a wire, a wiring circuit of a substrate, and the like.
- the thickness of the film adhesive 10 is 20 ⁇ m or more, a sufficient adhesive force tends to be obtained, and when the thickness of the film adhesive 10 is 200 ⁇ m or less, it is economical and the semiconductor device It is possible to meet the demand for downsizing.
- FIG. 3 is a schematic cross-sectional view showing an adhesive sheet according to another embodiment.
- the adhesive sheet 110 further includes a protective film 30 laminated on the surface of the film adhesive 10 opposite to the base 20.
- the protective film 30 may be the same as the above support film.
- the thickness of the protective film may be, for example, 15 to 200 ⁇ m or 70 to 170 ⁇ m.
- FIG. 4 is a schematic cross-sectional view showing a semiconductor device according to an embodiment.
- the first semiconductor element Wa in the first stage is wire-bonded to the substrate 14 via the first wire 88, and the second semiconductor element Waa is formed on the first semiconductor element Wa.
- the semiconductor device is a semiconductor device in which at least a part of the first wire 88 is embedded in the film adhesive 10 by being pressure-bonded via the film adhesive 10.
- the semiconductor device is a semiconductor device in which the first wire 88 and the first semiconductor element Wa are embedded even if the semiconductor device is a wire embedded type semiconductor device in which at least a part of the first wire 88 is embedded. May be.
- the substrate 14 and the second semiconductor element Waa are further electrically connected via the second wire 98, and the second semiconductor element Waa is sealed with the sealing material 42. ing.
- the thickness of the first semiconductor element Wa may be 10 to 170 ⁇ m, and the thickness of the second semiconductor element Waa may be 20 to 400 ⁇ m.
- the first semiconductor element Wa embedded in the film adhesive 10 is a controller chip for driving the semiconductor device 200.
- the substrate 14 is composed of an organic substrate 90 having two circuit patterns 84 and 94 formed on the surface thereof.
- the first semiconductor element Wa is pressure-bonded onto the circuit pattern 94 via an adhesive 41.
- the second semiconductor element Waa is interposed via the film adhesive 10 so that the circuit pattern 94, the first semiconductor element Wa, and the circuit pattern 84 to which the first semiconductor element Wa is not bonded are covered. Crimped to the substrate 14.
- a film adhesive 10 is embedded in the uneven steps due to the circuit patterns 84 and 94 on the substrate 14.
- the second semiconductor element Waa, the circuit pattern 84, and the second wire 98 are sealed with a resin sealing material 42.
- a die-bonding step embedded in the adhesive is
- the semiconductor device 200 is a semiconductor device in which a first wire 88 and a first semiconductor element Wa are embedded, and is manufactured by the following procedure.
- the first semiconductor element Wa having the adhesive 41 is crimped onto the circuit pattern 94 on the substrate 14, and the circuit pattern 84 on the substrate 14 and the first pattern are connected to each other via the first wire 88.
- the first semiconductor element Wa is electrically bonded and connected (first wire bonding step).
- the adhesive sheet 100 is laminated on one side of a semiconductor wafer (for example, thickness 100 ⁇ m, size: 8 inches), and the base material 20 is peeled off, whereby the film-like adhesive 10 (for example, thickness) is applied to one side of the semiconductor wafer. 110 ⁇ m). Then, after the dicing tape is bonded to the film adhesive 10, the dicing tape is diced to a predetermined size (for example, 7.5 mm square), whereby the second film adhesive 10 is applied as shown in FIG. The semiconductor element Waa is obtained (laminating step).
- the temperature condition of the laminating process may be 50-100 ° C or 60-80 ° C.
- the temperature in the laminating step is 50 ° C. or higher, good adhesion to the semiconductor wafer can be obtained.
- the temperature of the laminating process is 100 ° C. or lower, the film-like adhesive 10 can be prevented from flowing excessively during the laminating process, so that it is possible to prevent a change in thickness and the like.
- Examples of the dicing method include blade dicing using a rotary blade, and a method of cutting a film adhesive or both a wafer and a film adhesive with a laser.
- the second semiconductor element Waa to which the film adhesive 10 is attached is pressure-bonded to the substrate 14 to which the first semiconductor element Wa is bonded via the first wire 88.
- the first wire 88 and the first semiconductor element Wa are covered with the second semiconductor element Waa to which the film-like adhesive 10 is attached by the film-like adhesive 10.
- the second semiconductor element Waa is fixed to the substrate 14 by pressing the second semiconductor element Waa to the substrate 14 (die bonding step).
- the film adhesive 10 is preferably pressure-bonded for 0.5 to 3.0 seconds under conditions of 80 to 180 ° C. and 0.01 to 0.50 MPa.
- the film adhesive 10 is pressed and heated for 5 minutes or more under the conditions of 60 to 175 ° C. and 0.3 to 0.7 MPa.
- the circuit pattern 84, the second wire 98 and the second semiconductor element Waa are sealed with a sealing material 42.
- the semiconductor device 200 can be manufactured through such steps.
- the semiconductor device may be a wire embedded type semiconductor device in which at least a part of the first wire 88 is embedded.
- Examples 1 to 5 and Comparative Examples 1 to 3 ⁇ Preparation of adhesive sheet>
- a varnish of a thermosetting resin composition having a solid content of 40% by mass was prepared using cyclohexanone as a solvent.
- the obtained varnish was filtered through a 100-mesh filter and vacuum degassed.
- the varnish after vacuum defoaming was applied as a base film onto a polyethylene terephthalate (PET) film that had been subjected to a release treatment with a thickness of 38 ⁇ m.
- PET polyethylene terephthalate
- the applied varnish was heat-dried in two stages of 90 ° C. for 5 minutes, followed by 140 ° C. for 5 minutes.
- an adhesive sheet provided with a film adhesive having a thickness of 110 ⁇ m in a semi-cured (B stage) state was obtained on the base film.
- each component in Table 1 is as follows.
- Epoxy resin A-1 Dicyclopentadiene skeleton-containing epoxy resin, manufactured by DIC Corporation, trade name: HP-7200L, epoxy equivalent: 242 to 252 g / eq
- A-2 Cresol novolac type epoxy resin, manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., trade name: YDCN-700-10, epoxy equivalent: 209 g / eq
- A-3 Bisphenol F type epoxy resin (liquid at 25 ° C.), manufactured by DIC Corporation, trade name: EXA-830CRP, epoxy equivalent: 159 g / eq
- Curing agent B-1 Biphenyl aralkyl type phenol resin, manufactured by Air Water Co., Ltd., trade name: HE-200C-10, hydroxyl group equivalent: 205 g / eq
- B-2 Phenylaralkyl type phenol resin, manufactured by Air Water Co., Ltd., trade name: HE100C-30, hydroxyl group equivalent: 175 g
- C-2 Acrylic rubber, manufactured by Nagase ChemteX Corporation, trade name: SG-708-6, weight average molecular weight: 700,000, acid value: 9 mgKOH / g, Tg: 4 ° C.
- C-3 Acrylic rubber, manufactured by Nagase ChemteX Corporation, trade name: SG-280 EK23, weight average molecular weight: 900,000, acid value: 30 mgKOH / g, Tg: -29 ° C
- Second elastomer D-1 Acrylic rubber, manufactured by Nagase ChemteX Corporation, trade name: HTR-860P-3CSP, weight average molecular weight: 800,000, glycidyl group-containing monomer ratio: 3%, Tg: -7 °C
- E Inorganic filler
- E-1 Silica filler dispersion, fused silica, manufactured by Admatechs Co., Ltd., trade name: SC2050-HLG, average particle size: 0.50 ⁇ m
- F
- the film adhesive of the semiconductor chip A and the semiconductor wafer of the semiconductor chip B were pressure-bonded under the conditions of 120 ° C., 0.20 MPa, and 1.5 seconds to obtain an evaluation sample.
- alignment was performed so that the semiconductor chip B that was previously crimped was in the center of the semiconductor chip A.
- the evaluation sample thus obtained was observed for the presence or absence of observation of voids with an ultrasonic digital diagnostic imaging apparatus (Insight Inc., probe: 75 MHz), and when voids were observed, The ratio of the void area was calculated, and these analysis results were evaluated as embeddability.
- the evaluation criteria are as follows. The results are shown in Table 1. A: No void was observed. B: Although voids were observed, the ratio was less than 5 area%. C: A void was observed, and the ratio was 5 area% or more.
- thermosetting resin composition according to the present invention can suppress an increase in the amount of bleed during high-temperature pressure treatment while having good embedding property during thermocompression bonding. It was done.
- thermosetting resin composition according to the present invention has a good embedding property at the time of thermocompression bonding, and can suppress an increase in the amount of bleed at the time of high-temperature pressure treatment.
- a film-like adhesive formed by forming a product into a film can be useful as a chip-embedded film-like adhesive FOD (Film Over Die) or a wire-embedded film-like adhesive FOW (Film Over Wire) .
- SYMBOLS 10 Film adhesive, 14 ... Substrate, 20 ... Base material, 30 ... Protective film, 41 ... Adhesive, 42 ... Sealing material, 84, 94 ... Circuit pattern, 88 ... First wire, 90 ... Organic substrate 98, second wire, 100, 110, adhesive sheet, 200, semiconductor device, Wa, first semiconductor element, Waa, second semiconductor element.
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Abstract
L'invention concerne une composition de résine thermodurcissable comprenant : une résine époxy; un agent de durcissement; un premier élastomère ayant au moins un type de groupe fonctionnel choisi dans un groupe constitué d'un groupe carboxy et d'un groupe hydroxy; et un second élastomère qui n'a pas de groupe carboxy ou un groupe hydroxy.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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PCT/JP2018/002982 WO2019150433A1 (fr) | 2018-01-30 | 2018-01-30 | Composition de résine thermodurcissable, adhésif sous forme de film, feuille adhésive, et procédé de production de dispositif à semi-conducteur |
CN201980009495.5A CN111630643B (zh) | 2018-01-30 | 2019-01-18 | 热固化性树脂组合物、膜状粘接剂、粘接片材及半导体装置的制造方法 |
KR1020207021944A KR102561428B1 (ko) | 2018-01-30 | 2019-01-18 | 열경화성 수지 조성물, 필름형 접착제, 접착 시트 및 반도체 장치의 제조 방법 |
PCT/JP2019/001538 WO2019150995A1 (fr) | 2018-01-30 | 2019-01-18 | Composition de résine thermodurcissable, adhésif filmogène, feuille adhésive et procédé de production de dispositif à semi-conducteur |
JP2019569003A JP7283399B2 (ja) | 2018-01-30 | 2019-01-18 | 熱硬化性樹脂組成物、フィルム状接着剤、接着シート、及び半導体装置の製造方法 |
SG11202006827RA SG11202006827RA (en) | 2018-01-30 | 2019-01-18 | Thermosetting resin composition, film-form adhesive, adhesive sheet, and method for producing semiconductor device |
TW108103139A TWI785196B (zh) | 2018-01-30 | 2019-01-28 | 熱硬化性樹脂組成物、膜狀接著劑、接著片及半導體裝置的製造方法 |
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PCT/JP2019/001538 WO2019150995A1 (fr) | 2018-01-30 | 2019-01-18 | Composition de résine thermodurcissable, adhésif filmogène, feuille adhésive et procédé de production de dispositif à semi-conducteur |
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KR (1) | KR102561428B1 (fr) |
CN (1) | CN111630643B (fr) |
SG (1) | SG11202006827RA (fr) |
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KR20200115515A (ko) | 2020-10-07 |
JPWO2019150995A1 (ja) | 2021-02-25 |
SG11202006827RA (en) | 2020-08-28 |
CN111630643B (zh) | 2023-07-07 |
CN111630643A (zh) | 2020-09-04 |
WO2019150995A1 (fr) | 2019-08-08 |
TW201940635A (zh) | 2019-10-16 |
JP7283399B2 (ja) | 2023-05-30 |
TWI785196B (zh) | 2022-12-01 |
KR102561428B1 (ko) | 2023-07-31 |
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