WO2019208614A1 - 樹脂組成物、積層体、樹脂組成物層付き半導体ウェハ、樹脂組成物層付き半導体搭載用基板、及び半導体装置 - Google Patents
樹脂組成物、積層体、樹脂組成物層付き半導体ウェハ、樹脂組成物層付き半導体搭載用基板、及び半導体装置 Download PDFInfo
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- WO2019208614A1 WO2019208614A1 PCT/JP2019/017363 JP2019017363W WO2019208614A1 WO 2019208614 A1 WO2019208614 A1 WO 2019208614A1 JP 2019017363 W JP2019017363 W JP 2019017363W WO 2019208614 A1 WO2019208614 A1 WO 2019208614A1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 claims description 5
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 5
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- AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 claims description 4
- IKFPAKYBSYICFK-UHFFFAOYSA-N 1-[4-(4-propylphenoxy)phenyl]pyrrole-2,5-dione Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N2C(C=CC2=O)=O)C=C1 IKFPAKYBSYICFK-UHFFFAOYSA-N 0.000 claims description 4
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- MJFCOXATGBYERZ-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(Br)C=N1 MJFCOXATGBYERZ-UHFFFAOYSA-N 0.000 description 1
- KUSIBMGCSKLUCE-UHFFFAOYSA-N n-(5-iodopyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(I)C=N1 KUSIBMGCSKLUCE-UHFFFAOYSA-N 0.000 description 1
- AUDGAMZNNDGYAX-UHFFFAOYSA-N n-(benzotriazol-1-ylmethyl)formamide Chemical compound C1=CC=C2N(CNC=O)N=NC2=C1 AUDGAMZNNDGYAX-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
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- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
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- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
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- OTVZGAXESBAAQQ-UHFFFAOYSA-N pyrazine-2,3-dicarbonitrile Chemical compound N#CC1=NC=CN=C1C#N OTVZGAXESBAAQQ-UHFFFAOYSA-N 0.000 description 1
- ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical compound OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- WOFKFNZIJZWWPZ-UHFFFAOYSA-N pyrene-1,3-diamine Chemical compound C1=C2C(N)=CC(N)=C(C=C3)C2=C2C3=CC=CC2=C1 WOFKFNZIJZWWPZ-UHFFFAOYSA-N 0.000 description 1
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 description 1
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
- HZFPPBMKGYINDF-UHFFFAOYSA-N pyrimidin-5-ylboronic acid Chemical compound OB(O)C1=CN=CN=C1 HZFPPBMKGYINDF-UHFFFAOYSA-N 0.000 description 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 description 1
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
- HMZIGHBQOOGZAK-UHFFFAOYSA-N pyrimidine-2-sulfonyl fluoride Chemical compound FS(=O)(=O)C1=NC=CC=N1 HMZIGHBQOOGZAK-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- JBKICBDXAZNSKA-UHFFFAOYSA-N tcmdc-123507 Chemical compound C1=CC=C2NC(C=3C=CC=C(N=3)C=3NC4=CC=CC=C4N=3)=NC2=C1 JBKICBDXAZNSKA-UHFFFAOYSA-N 0.000 description 1
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 1
- POTDIELOEHTPJN-UHFFFAOYSA-N tert-butyl (4,6-dimethylpyrimidin-2-yl)sulfanylformate Chemical compound CC1=CC(C)=NC(SC(=O)OC(C)(C)C)=N1 POTDIELOEHTPJN-UHFFFAOYSA-N 0.000 description 1
- XWUFRDJEUOAMNW-UHFFFAOYSA-N tert-butyl 1,2,4-triazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=NC=N1 XWUFRDJEUOAMNW-UHFFFAOYSA-N 0.000 description 1
- MTBKGWHHOBJMHJ-UHFFFAOYSA-N tert-butyl imidazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CN=C1 MTBKGWHHOBJMHJ-UHFFFAOYSA-N 0.000 description 1
- IEUIEMIRUXSXCL-UHFFFAOYSA-N tert-butyl n-(3-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(N)=C1 IEUIEMIRUXSXCL-UHFFFAOYSA-N 0.000 description 1
- KEKAANXUQSMDMK-UHFFFAOYSA-N tert-butyl n-(6-aminopyridin-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(N)=N1 KEKAANXUQSMDMK-UHFFFAOYSA-N 0.000 description 1
- IGSFMHYSWZUENI-UHFFFAOYSA-N tert-butyl n-[amino(pyrazol-1-yl)methylidene]carbamate Chemical compound CC(C)(C)OC(=O)N=C(N)N1C=CC=N1 IGSFMHYSWZUENI-UHFFFAOYSA-N 0.000 description 1
- VUENSYJCBOSTCS-UHFFFAOYSA-N tert-butyl-imidazol-1-yl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)N1C=CN=C1 VUENSYJCBOSTCS-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- GFNNBHLJANVSQV-UHFFFAOYSA-N tyrphostin AG 1478 Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1 GFNNBHLJANVSQV-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
- H01L21/563—Encapsulation of active face of flip-chip device, e.g. underfilling or underencapsulation of flip-chip, encapsulation preform on chip or mounting substrate
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
Definitions
- the present invention relates to a resin composition, a laminate using the resin composition, a semiconductor wafer with a resin composition layer, a semiconductor mounting substrate with a resin composition layer, and a semiconductor device. Specifically, the present invention relates to a resin composition useful as an underfill material.
- a semiconductor chip (hereinafter sometimes abbreviated as “chip”) is mounted on a semiconductor mounting substrate (hereinafter sometimes abbreviated as “substrate”).
- substrate a semiconductor mounting substrate
- flip chip mounting has attracted attention.
- flip-chip mounting a method of bonding a chip and a substrate, filling an underfill material in a gap between the chip and the substrate, and curing is generally used.
- the pitch of electrodes arranged on a chip and the gap between electrodes have progressed, and the workability has deteriorated due to the long filling time of the underfill material.
- a flux component derived from carboxylic acid or the like may be added to the pre-applied underfill material.
- Patent Document 1 describes a pre-applied underfill material using an epoxy compound.
- Patent Document 2 also describes a pre-applied underfill material using an epoxy compound.
- Patent Document 3 describes a pre-applied underfill material using an epoxy compound and a flux component.
- Patent Document 4 describes an underfill material using an acrylic monomer.
- Patent Document 5 describes a pre-applied underfill material using a radical polymerizable monomer.
- Patent Document 6 includes a film having a copper ion adsorption layer containing a resin having a skeleton capable of complexing with copper ions, wherein the resin having a skeleton capable of complexing with copper ions is a phenol resin having a triazine skeleton There is a description of the adhesive.
- JP 2008-133423 A JP 2016-027174 A JP 2013-112730 A Japanese Patent Laying-Open No. 2015-172145 Special table 2015-503220 gazette JP 2011-52109 A
- Patent Document 3 a specific carboxyl group-containing compound is used as a flux component.
- the carboxyl group-containing compound has a drawback that it reacts slightly with the epoxy compound even at room temperature and the flux activity decreases with time during storage, so that the bonding stability is low and the mass productivity is poor.
- Patent Document 4 since the flux component is intentionally not included, the oxide film at the joint cannot be removed before the metal joining.
- Patent Document 5 a thermal radical initiator is used as a polymerization initiator for a radical polymerizable monomer.
- a thermal radical initiator is used as a polymerization initiator for a radical polymerizable monomer.
- Patent Document 5 although a polymer containing a carboxyl group is used, since the molecular weight is large, the mobility of the carboxyl group is low, and sufficient flux activity cannot be expected.
- Patent Document 6 describes a film adhesive containing a phenol resin having a triazine skeleton that is a skeleton capable of complexing with copper ions.
- this adhesive has a problem that since a phenol component having a triazine skeleton is incorporated in the resin skeleton, the mobility is low, and the metal oxide film removability at the joint is extremely low.
- the present invention has been made in view of such problems, and has excellent flux activity, flexibility, and storage stability, and is suitable for an underfill material, a laminate, and a resin composition.
- the object is to provide a semiconductor wafer with a physical layer, a semiconductor mounting substrate with a resin composition layer, and a semiconductor device.
- the present inventors contain a compound (A) having a phenolic hydroxyl group, a metal ion scavenger (B), and a radical polymerizable compound (C).
- A a compound having a phenolic hydroxyl group
- B a metal ion scavenger
- C a radical polymerizable compound
- a resin composition comprising a compound (A) having a phenolic hydroxyl group, a metal ion scavenger (B), and a radical polymerizable compound (C).
- the metal ion scavenger (B) is 2,4-diamino-6-methyl-1,3,5-triazine, 2,2′-bipyridine, 1,3-diphenyl-1,3-propanedione 1- (2-mesitylene) -1,3-butanedione, 1,3-bis (4-methoxyphenyl) -1,3-propanedione, 1- (4-tert-butylphenyl) -3- (4- Selected from the group consisting of methoxyphenyl) -1,3-propanedione, and (E, E) -1,7-bis (4-hydroxy-3-methoxyphenyl) -1,6-heptadiene-3,5-dione
- the resin composition according to any one of [1] to [6], which contains at least one selected from the above.
- the metal ion scavenger (B) is 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) -1,3-propanedione, and (E, E) -1,7 Any one of [1] to [8], comprising at least one selected from the group consisting of -bis (4-hydroxy-3-methoxyphenyl) -1,6-heptadiene-3,5-dione
- radical polymerizable compound (C) contains at least one selected from the group consisting of a (meth) acrylate compound, a maleimide compound, and a propenyl compound.
- the radical polymerizable compound (C) is 2,2′-bis ⁇ 4- (4-maleimidophenoxy) phenyl ⁇ propane, 1,2-bis (maleimide) ethane, 1,4-bis (maleimide). Butane, 1,6-bis (maleimido) hexane, N, N′-1,3-phenylenedimaleimide, N, N′-1,4-phenylenedimaleimide, N-phenylmaleimide, represented by the following formula (1)
- the resin according to [10] comprising at least one selected from the group consisting of a maleimide compound represented by the following formula (2) and a maleimide compound represented by the following formula (3): Composition.
- each R 1 independently represents a hydrogen atom or a methyl group, and n 1 represents an integer of 1 or more.
- n 2 1 to 30.
- each R 2 independently represents a hydrogen atom, a methyl group or an ethyl group
- each R 3 independently represents a hydrogen atom or a methyl group
- the radical polymerizable compound (C) is 2,2′-bis ⁇ 4- (4-maleimidophenoxy) phenyl ⁇ propane, a maleimide compound represented by the formula (1), and the formula (2).
- the content of the compound (A) having the phenolic hydroxyl group in the resin composition is 5 masses with respect to 100 mass parts of the total amount of the radical polymerizable compound (C) in the resin composition.
- the content of the metal ion scavenger (B) in the resin composition is 5 parts by mass or more with respect to 100 parts by mass of the total amount of the radical polymerizable compound (C) in the resin composition.
- the inorganic filler (D) contains at least one selected from the group consisting of silica, aluminum hydroxide, alumina, boehmite, boron nitride, aluminum nitride, magnesium oxide, and magnesium hydroxide.
- the resin composition according to any one of [17].
- the content of the inorganic filler (D) in the resin composition is 300 parts by mass or less with respect to 100 parts by mass of the total amount of the radical polymerizable compound (C).
- the flexibility-imparting component (E) contains a thermoplastic polymer compound, and the polymer compound has a mass average molecular weight of 1,000 or more and 1,000,000 or less.
- a laminate comprising a supporting substrate and a layer containing the resin composition according to any one of [1] to [23] laminated on the supporting substrate.
- a semiconductor with a resin composition layer comprising: a semiconductor wafer; and the laminate according to [24] laminated on the semiconductor wafer, wherein the layer containing the resin composition is laminated on the semiconductor wafer. Wafer.
- a semiconductor device comprising the semiconductor wafer with a resin composition layer according to [25] and / or the semiconductor mounting substrate with a resin composition layer according to [26].
- a resin composition, a laminate, a semiconductor wafer with a resin composition layer, and a resin composition layer that have excellent flux activity, flexibility, and storage stability and are suitable for underfill materials A semiconductor mounting substrate and a semiconductor device can be provided.
- (meth) acrylo means both “acrylo” and the corresponding “methacrylo”.
- (Meth) acryl means both “acryl” and the corresponding “methacryl”.
- (Meth) acrylate” means both “acrylate” and the corresponding “methacrylate”.
- the resin composition of one embodiment of the present embodiment contains a compound (A) having a phenolic hydroxyl group, a metal ion scavenger (B), and a radical polymerizable compound (C).
- the resin composition of this embodiment is preferable for the use of an underfill material, and is preferably used for the use of a pre-applied underfill material.
- the resin composition of another aspect of the present embodiment further contains an inorganic filler (D) in each of the components.
- the resin composition according to another aspect of the present embodiment further contains a flexibility imparting component (E) in addition to the components described above.
- Another aspect of this embodiment is a laminate (hereinafter, also referred to as “resin laminate”) obtained using the resin composition according to this embodiment, and a semiconductor with a resin composition layer produced using the laminate.
- resin laminate a laminate obtained using the resin composition according to this embodiment, and a semiconductor with a resin composition layer produced using the laminate.
- a semiconductor mounting substrate with a resin composition layer produced using a wafer, a laminate, and a semiconductor device produced using the resin composition of the present embodiment are also provided.
- the resin composition of the present embodiment is preferably a resin composition used as an underfill material used for flip chip mounting of a chip.
- This resin composition contains a compound (A) having a phenolic hydroxyl group, a metal ion scavenger (B), and a radical polymerizable compound (C).
- the resin composition of this embodiment may further contain an inorganic filler (D) and / or a flexibility imparting component (E).
- the compound (A) having a phenolic hydroxyl group is a component mainly contributing to the flux activity of the resin composition.
- the compound (A) having a phenolic hydroxyl group is not particularly limited as long as it is a compound having one or more phenolic hydroxyl groups in the molecule.
- the compound (A) may be a phenol resin.
- the compound (A) having a phenolic hydroxyl group is volatilized before the flux activity is manifested during flip-chip mounting, that is, the compound (A) having a phenolic hydroxyl group is removed before removing the oxide film at the junction. It is preferable to prevent volatilization.
- the molecular weight of the compound (A) having a phenolic hydroxyl group is not particularly limited as long as the effect of the present embodiment is exerted, but is preferably 200 or more, and is a viewpoint of reducing the volatile content during thermosetting. Therefore, it is more preferably 250 or more, and further preferably 300 or more from the viewpoint of reducing the volatile content in flip chip bonding.
- the molecular weight of the compound (A) having a phenolic hydroxyl group is preferably 10,000 or less from the viewpoint of having mobility as an acid and obtaining more sufficient flux activity, and from the viewpoint of solvent solubility. Is preferably 8,000 or less, and more preferably 6,000 or less from the viewpoint of ensuring mobility for efficiently reaching the metal oxide film at the joint in flip chip bonding.
- the molecular weight represents the molecular weight of the compound when it is a compound, and represents the mass average molecular weight (Mw) when it is a resin.
- the mass average molecular weight can be determined using polystyrene as a standard substance by GPC (gel permeation chromatogram) method.
- the melting point of the compound (A) having a phenolic hydroxyl group is not particularly limited as long as the effect of the present embodiment is exhibited, but is preferably 300 ° C. or lower, and melts below the melting point of general solder and acts on the metal oxide film. From the viewpoint of melting, it is more preferably 0 to 260 ° C., and from the viewpoint of melting at or below the melting point of the solder used for the flip chip bonding while ensuring storage stability at room temperature, More preferably, it is 240 degreeC.
- the 5% mass reduction temperature of the compound (A) having a phenolic hydroxyl group is not particularly limited as long as the effect of the present embodiment is exhibited, but is preferably 250 ° C. or higher, and suppresses volatile matter during heating in the semiconductor device manufacturing process.
- the temperature is more preferably 260 ° C. or higher, and further preferably 270 ° C. or higher for the reason of suppressing volatile components during flip chip bonding. If the 5% mass reduction temperature is less than 250 ° C., a large amount of volatile components are generated during flip chip bonding, which may cause voids in the cured product and process contamination.
- the 5% mass reduction temperature of the compound (A) having a phenolic hydroxyl group can be measured using thermal mass spectrometry (TGA). The measurement method will be specifically described. A predetermined amount of the compound is charged into TGA and heated from room temperature to 500 ° C. at 10 ° C./min. A temperature at which the mass is reduced by 5% from the obtained mass reduction curve is defined as a 5% mass reduction temperature.
- Examples of the compound (A) having a phenolic hydroxyl group include 9,9′-bis- (4-hydroxy-3-methylphenyl) fluorene, biscresol fluorene, bisphenol fluorene, 2,4,6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) mesitylene, hesperidin, ⁇ , ⁇ ′, ⁇ ′′ -tris (4-hydroxyphenyl) -1-ethyl-4-isopropylbenzene, ⁇ , ⁇ ′-bis ( 4-hydroxy-3,5-dimethylphenyl) -1,4-diisopropylbenzene, 4,4′-methylenebis (2,6-di-tert-butylphenol), 1,1 ′, 3-tris (2,5- Dimethyl-4-hydroxyphenyl) -3-phenylpropane, 4,4 ′-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl]
- phenol resin which is the compound (A) having a phenolic hydroxyl group examples include, for example, bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolac resin, and bisphenol A.
- Novolac type phenol resin Novolac type phenol resin, glycidyl ester type phenol resin, aralkyl novolac type phenol resin, biphenyl aralkyl type phenol resin, cresol novolac type phenol resin, polyfunctional phenol resin, naphthol resin, naphthol novolak resin, polyfunctional naphthol resin, anthracene type phenol resin , Naphthalene skeleton modified novolak type phenol resin, phenol aralkyl type phenol resin, naphthol aralkyl type phenol resin Resin, dicyclopentadiene type phenol resin, biphenyl type phenol resin, alicyclic phenol resin, polyol type phenol resin, phosphorus containing phenol resin, hydroxyl group containing silicone resins, propenyl phenol resin, allyl phenol resin, propenyl biphenylene resin Can be mentioned.
- the compound (A) having a phenolic hydroxyl group a commercially available product may be used.
- PHENOLITE registered trademark
- KA-1163 manufactured by DIC Corporation
- TBIS registered trademark
- -MP manufactured by Taoka Chemical Industry Co., Ltd.
- SN-495V manufactured by Nippon Steel Chemical Co., Ltd.
- LVA01 manufactured by Gunei Chemical Industry Co., Ltd.
- BPN01 manufactured by Gunei Chemical Industry Co., Ltd.
- the content of the compound (A) having a phenolic hydroxyl group in the resin composition is not particularly limited as long as the effect of the present embodiment is achieved, but the total amount of the following radical polymerizable compounds (C) in the resin composition is 100. It is preferably 5 parts by mass or more and 50 parts by mass or less with respect to parts by mass, and more preferably 10 parts by mass or more and 45 parts by mass or less from the viewpoint of ensuring sufficient flux activity and solvent solubility. From the viewpoint of ensuring the flux activity, solvent solubility, and flexibility of the resin composition, it is more preferably 15 parts by mass or more and 40 parts by mass or less.
- the metal ion scavenger (B) is not particularly limited as long as it is a compound that can capture metal ions.
- the metal ion to be trapped is not particularly limited, but copper ion is preferable.
- the metal ion scavenger (B) is not particularly limited as long as the effect of the present embodiment is exhibited, but at least one selected from nitrogen and oxygen as a coordination atom can be suitably captured metal ions, particularly copper ions. It is preferable to contain these elements.
- the metal ion scavenger containing nitrogen as a coordination atom is not particularly limited, and examples thereof include amines and amine derivatives.
- the metal scavenger containing oxygen as a coordination atom is not particularly limited, and examples thereof include ether derivatives and ketone derivatives.
- Examples of amine derivatives include imidazole derivatives, triazole derivatives, pyrazole derivatives, triazine derivatives, pyridine derivatives, terpyridine derivatives, bipyridine derivatives, phenanthroline derivatives, pyrimidine derivatives, pyrazine derivatives, pyridazine derivatives, quinazoline derivatives, porphyrin derivatives, phthalocyanine derivatives, and A cyclen derivative is mentioned.
- Examples of the ether derivative include a crown ether derivative.
- Examples of the ketone derivative include a diketone derivative.
- amines examples include 1,3-phenylenediamine, 2,6-diaminotoluene, 1,3-diaminopyrene, 2,4-diaminotoluene, 2,4,6-trimethyl-1,3-phenylenediamine, 2,4-diaminodiphenylamine, 3-acetamidoaniline, 1,2-diamino-4-nitrobenzene, 4-nitro-1,3-phenylenediamine, 2-methyl-5-nitroaniline, 3,5-diaminobenzoic acid, 2-amino-1-methylamino-4-nitrobenzene, 3-acetamido-4-methylaniline, N- (tert-butoxycarbonyl) -1,3-phenylenediamine, 3′-amino-4′-methoxyacetanilide, 3 -(4-Methyl-1-piperazinyl) aniline is mentioned.
- imidazole derivatives examples include imidazole, N-acetylimidazole, 1- ( ⁇ , 4-diphenylbenzyl) imidazole, 2,2 ′-(2,6-pyridinediyl) bis (benzimidazole), 4- (4, 5-diphenyl-1H-imidazol-2-yl) benzoic acid, 2- (4-hydroxyphenyl) -4,5-diphenylimidazole, 5-chloro-1- [1- [3- (2-oxo-1- Benzimidazolyl) propyl] -4-piperidyl] benzimidazol-2-one, methyl [5- (4-fluorobenzoyl) benzimidazol-2-yl] carbamate, 2- (4-fluorophenyl) -4,5-diphenyl Imidazole, 2-heptadecylimidazole, 2-[[[3-methyl-4- (2,2,2-trifluoro Roethoxy) -2-pyri
- triazole derivatives examples include 1-aminobenzotriazole, 2-aminobenzotriazole, 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole, and 3-amino-5-mercapto-1,2.
- pyrazole derivative examples include pyrazole, 1-allyl-3,5-dimethylpyrazole, 3-amino-5-tert-butylpyrazole, 5-amino-1,3-diphenylpyrazole, 5-amino-1- (2 -Hydroxyethyl) pyrazole, 3-amino-5-hydroxypyrazole, 5-amino-3- (4-methoxyphenyl) -1-phenylpyrazole, 3-amino-5- (4-methoxyphenyl) pyrazole, 5-amino -3-Methyl-1-phenylpyrazole, 4-amino-1-methyl-3-propylpyrazole-5-carboxamide, 3-amino-1-methylpyrazole, 3-amino-5-methylpyrazole, 5-amino-3 -Methyl-1-p-tolylpyrazole, 3-amino-5-phenylpyrazole, 5-amino-1 Phenylpyrazole, 3-amino-1
- triazine derivatives include 3-amino-5,6-dimethyl-1,2,4-triazine, 2-amino-4-methoxy-6-methyl-1,3,5-triazine, and 6-amino-1 , 3,5-triazine-2,4-diol, 2,4-diamino-6-hydroxy-1,3,5-triazine, 2-amino-4-hydroxy-1,3,5-triazine, 2,4 -Diamino-6-phenyl-1,3,5-triazine, 2- (tert-butylamino) -4- (cyclopropylamino) -6- (methylthio) -1,3,5-triazine, 2,4- Diamino-6- (cyclopropylamino) -1,3,5-triazine, 2,4-diamino-6-butylamino-1,3,5-triazine, 2,4-diamino-6-diallylamino-1, 3,5-tria 2,4-d
- Examples of the pyridine derivative include 5-bromopyridine-3-carboxamide, 4- (4-aminophenoxy) -N-methyl-2-pyridinecarboxamide, 2,6-bis [(2R, 4S, 5S) -1- Benzyl-4,5-diphenylimidazolidin-2-yl] pyridine, 2,6-bis [3- (9H-carbazol-9-yl) phenyl] pyridine, 2,6-bis [(2S, 5S) -4 , 4-Diphenyl-1-aza-3-oxabicyclo [3.3.0] octan-2-yl] pyridine, 2,6-bis [(2S, 4S) -4-methyl-5,5-diphenyloxazolidine -2-yl] pyridine, 2,6-bis (9H-carbazol-9-yl) pyridine, 3,5-di (1-pyrenyl) pyridine, 2,6-bis (2-benzimidazolyl) pi Gin, (R, R
- Examples of the terpyridine derivative include 4 ′-(4-bromophenyl) -2,2 ′: 6 ′, 2 ′′ -terpyridine, 4′-bromo-2,2 ′: 6 ′, 2 ′′ -terpyridine, 2,2 ′: 6 ′, 2 ′′ -terpyridine-4′-diethyl phosphonate, 1,4-di [[2,2 ′: 6 ′, 2 ′′ -terpyridine] -4′-yl] benzene, 4 ′-(methoxycarbonyl) -2,2 ′: 6 ′, 2 ′′ -terpyridine, 2,2 ′: 6 ′, 2 ′′ -terpyridine, 2,2 ′: 6 ′, 2 ′′ -terpyridine— Examples include trimethyl 4,4 ′, 4 ′′ -tricarboxylate.
- bipyridine derivative examples include 2,2′-bipyridine-6-carbonitrile, 2,2′-bipyridine-3,3′-dicarboxylic acid, 2,2′-bipyridine-4,4′-dicarboxylic acid, 2 2,2'-bipyridine-5,5'-dicarboxylic acid, 2,2'-bipyridine-6,6'-dicarboxylic acid, 2,2'-bipyridine-3,3'-diol, 2,2'-bipyridine- 6,6'-diol, 2,2'-bipyridine, 2,4'-bipyridine, 3,3'-bipyridine, 4,4'-bipyridine, 6,6'-bis (chloromethyl) -2,2 ' -Bipyridine, 4,4'-bis (5-hexyl-2-thienyl) -2,2'-bipyridine, 4,4'-bis (hydroxymethyl) -2,2'-bipyridine, 1,2-bis ( 4'--
- phenanthroline derivatives examples include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 2-bromo-1,10-phenanthroline, and 3-bromo.
- pyrimidine derivatives examples include pyrimidine, 4-methylpyrimidine, 5-aminopyrimidine, 2-aminopyrimidine, 4-aminopyrimidine, 4 (3H) -pyrimidinone, 2-chloropyrimidine, 2-mercaptopyrimidine, 2-cyanopyrimidine.
- pyrazine derivatives include pyrazine, 2-acetyl-3-ethylpyrazine, 2-acetyl-3-methylpyrazine, 2-acetylpyrazine, 2-amino-5-bromo-3-methoxypyrazine, 2-amino-5.
- pyridazine derivatives include pyridazine, 3-amino-6-chloropyridazine, 3-aminopyridazine, 3-bromoimidazo “1,2-b” pyridazine, 6-chloroimidazo “1,2-b” pyridazine, 3 -Chloro-6-methoxypyridazine, 3-chloro-6-methylpyridazine, 3-chloro-6-phenylpyridazine, 6-chloro-3 (2H) -pyridazinone, 3,6-dibromopyridazine, 3,6-dichloro- 4-methylpyridazine, 3,5-dichloropyridazine, 3,6-dichloropyridazine, 4,5-dichloro-3 (2H) -pyridazinone, 6-hydroxypyridazine-3-carboxylic acid, imidazo “1,2-b” Pyrid
- quinazoline derivatives examples include quinazoline, 6-acetoxy-7-methoxy-3H-quinazolin-4-one, 4-amino-2-chloro-6,7-dimethoxyquinazoline, 7-benzyloxy-6-methoxy-3H.
- porphyrin derivatives include porphyrin, 5,15-diphenylporphyrin, 2,3,7,8,12,13,17,18-octaethylporphyrin, 2,3,7,8,12,13,17, 18-octafluoro-5,10,15,20-tetrakis (pentafluorophenyl) porphyrin, meso-tetraphenylchlorin, tetraphenylporphyrin, 5,10,15,20-tetrakis (4-methoxyphenyl) porphyrin, 5, 10,15,20-tetrakis (2,6-dichlorophenyl) porphyrin, 5,10,15,20-tetrakis (4-carboxymethyloxyphenyl) porphyrin, 5,10,15,20-tetrakis (4-hydroxyphenyl) Porphyrin, 5,10,15,20- Trakis (2,4,6-trimethylphenyl
- phthalocyanine derivative examples include phthalocyanine, naphthalocyanine, and azurenocyanine.
- cyclen derivative examples include 1,4,7,10-tetraazacyclododecane, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, 1,4,7, 10-tetraazacyclododecane-1,4,7-triacetic acid tri-tert-butyl, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid tri-tert-butyl, 1,4,7,10-tetrabenzyl-1,4,7,10-tetraazacyclododecane.
- crown ether derivatives include 12-crown 4-ether, 2- (hydroxymethyl) -12-crown 4-ether, benzo-12-crown 4-ether, 15-crown 5-ether, 2- (hydroxymethyl) ) -15-crown 5-ether, benzo-15-crown 5-ether, dibenzo-15-crown 5-ether, 4′-bromobenzo-15-crown 5-ether, 4′-aminobenzo-15-crown 5-ether 4'-formylbenzo-15-crown 5-ether, 4'-acetylbenzo-15-crown 5-ether, 4'-carboxybenzo-15-crown 5-ether, 4'-nitrobenzo-15-crown 5-ether Ether, 18-crown 6-ether, 2- (hydroxymethyl)- 8-crown 6-ether, dicyclohexano-18-crown 6-ether, benzo-18-crown 6-ether, dibenzo-18-crown 6-ether, 4′-bromobenzo-18-crown 6-ether, 4
- Examples of the diketone derivative include 1,3-diphenyl-1,3-propanedione, 1- (2-mesitylene) -1,3-butanedione, and 1,3-bis, from the viewpoint of forming a complex with a metal ion.
- the metal ion scavenger (B) is preferably, for example, a triazine derivative, a bipyridine derivative, or a diketone derivative from the viewpoint of ensuring good storage stability of the varnish of the resin composition, and 2,4-diamino-6-methyl.
- metal ion scavengers (B) can be used singly or in combination of two or more.
- the content of the metal ion scavenger (B) in the resin composition is not particularly limited as long as the effect of the present embodiment is achieved, but the total amount of the following radical polymerizable compound (C) in the resin composition is 100 parts by mass. Is preferably 5 parts by weight or more and 50 parts by weight or less, more preferably 10 parts by weight or more and 45 parts by weight or less from the viewpoint of ensuring solvent solubility and sufficient flux activity. From the viewpoint of ensuring the activity and flexibility of the resin composition, it is more preferably 15 parts by mass or more and 40 parts by mass or less.
- Examples of (meth) acrylate compounds include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, isobutyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tri Methylolpropane tri (meth) acrylate, tetramethylolmethanetetra (meth) acrylate, 2-hydroxy-1,3-di (meth) acryloxypropane, 2,2-bis [4-((meth) acryloxymethoxy) phenyl ] Propane, 2,2-bis [4-((meth) acryloxypolyethoxy) phenyl] propane, dicyclopentenyl (meth) acrylate, tricyclodecanyl (meth) acrylate, tris ((meth) acryloyloxye Le) isocyanurate, and a
- the maleimide compound is not particularly limited as long as it is a compound having one or more maleimide groups in the molecule.
- each R 1 independently represents a hydrogen atom or a methyl group, and is preferably a hydrogen atom from the viewpoint of more effectively and reliably achieving the effects of the present embodiment.
- n 1 represents an integer of 1 or more, and the upper limit value of n 1 is usually 10, and is preferably 1 to 3 from the viewpoint of solubility in an organic solvent.
- the average value of n 2 is in the range of 1 to 30. From the viewpoint of more effectively and surely achieving the operational effects of the present embodiment, n 2 is preferably 7 or more and 30 or less, and more preferably 7 or more and 18 or less, as an average value.
- each R 2 independently represents a hydrogen atom, a methyl group or an ethyl group.
- each R 3 independently represents a hydrogen atom or a methyl group.
- the maleimide compound includes a maleimide compound represented by the above formula (1) from the viewpoint of solubility in an organic solvent and flexibility, together with 2,2-bis ⁇ 4- (4-maleimide). More preferably, it contains at least one maleimide compound selected from the group consisting of phenoxy) phenyl ⁇ propane, a maleimide compound represented by the formula (2), and a maleimide compound represented by the formula (3). .
- the maleimide compound is represented by the formula (1) with respect to 100 parts by mass of the total amount of the maleimide compound, from the viewpoint of having a good balance of excellent flux activity, excellent flexibility, and low thermal expansion coefficient. 5 parts by mass or more and 50 parts by mass or less is preferable, and the maleimide compound represented by the formula (2) is preferably contained by 5 parts by mass or more and 70 parts by mass or less, and is represented by the formula (3).
- the maleimide compound is preferably contained in an amount of 5 to 50 parts by mass, and 2,2-bis ⁇ 4- (4-maleimidophenoxy) phenyl ⁇ propane is preferably contained in an amount of 5 to 50 parts by mass.
- the maleimide compound can also be contained in the resin composition in the form of a prepolymer obtained by polymerizing a maleimide compound or a prepolymer obtained by polymerizing a maleimide compound with another compound such as an amine compound.
- a commercially available maleimide compound may be used.
- BMI-2300 manufactured by Daiwa Kasei Kogyo Co., Ltd.
- BMI-2300 manufactured by Daiwa Kasei Kogyo Co., Ltd.
- propenyl compounds include propenylbenzene, propenylnaphthalene, propenylanthracene, propenylphenol, monofunctional propenyl compounds of o-propenylphenoxybenzene; bispropenylphenyl ether, 2,2-bis [4- (o-propenylphenoxy) phenyl ] Propane, bis [4- (o-propenylphenoxy) phenyl] ether, bis [4- (o-propenylphenoxy) phenyl] sulfone, 4,4′-bis (o-propenylphenoxy) benzophenone, 2,2-bis [4- (o-propenylphenoxy) phenyl] nonane, 2,2-bis [3-tertiarybutyl-4- (o-propenylphenoxy) phenyl] propane, 2,2-bis [3-secondarybutyl-4- (O-propenyl fe Noxy) phenyl] propane
- radical polymerizable compounds (C) can be used alone or in combination of two or more.
- the resin composition of this embodiment can contain an inorganic filler (D) for improving the flame resistance, improving the thermal conductivity, and reducing the thermal expansion coefficient.
- an inorganic filler By using an inorganic filler, the flame resistance and thermal conductivity of the resin composition and the like can be improved, and the thermal expansion coefficient can be reduced.
- the inorganic filler (D) has electrical insulation
- the resin composition of this embodiment is used as a material for an underfill material, preferably a pre-applied underfill material, electrical insulation between the electrodes of the chip. Is preferable from the viewpoint of securing a sufficient amount.
- “electrical insulation” means that the volume resistivity at room temperature is 10 12 ⁇ ⁇ cm or more.
- inorganic filler For example, Silica, such as a fused silica; Aluminum compounds, such as boehmite, aluminum hydroxide, an alumina, and aluminum nitride; Magnesium oxide, Magnesium hydroxide, etc. Compounds: Calcium compounds such as calcium carbonate and calcium sulfate; molybdenum compounds such as molybdenum oxide and zinc molybdate; boron nitride; barium sulfate; talc such as natural talc and calcined talc; mica; short fiber glass, spherical glass And glass such as fine powder glass (for example, E glass, T glass, D glass).
- Silica such as a fused silica
- Aluminum compounds such as boehmite, aluminum hydroxide, an alumina, and aluminum nitride
- Magnesium oxide Magnesium hydroxide, etc.
- Compounds Calcium compounds such as calcium carbonate and calcium sulfate; moly
- the inorganic filler (D) includes silica, aluminum hydroxide, alumina, boehmite, boron nitride, aluminum nitride, magnesium oxide, And magnesium hydroxide are preferable, and silica is more preferable.
- fused silica is more preferable from the viewpoints of enhancing the filling property, fluidity of the underfill material into a fine space, and low thermal expansion.
- fused silica examples include SFP-120MC and SFP-130MC manufactured by DENKA CORPORATION, SC1050-MLQ, SC2050-MNU, SC2050-MTX, SE2053-SQ, YA050C-MJF, and YA050C manufactured by ADMATEX. -MJA.
- the average particle diameter of the inorganic filler (D) is not limited, but when the resin composition of the present invention is used as an underfill material, preferably as a pre-applied underfill material, the pitch of electrodes arranged on a chip is reduced. And from the viewpoint of reducing the gap between the electrodes, it is preferably 3 ⁇ m or less, more preferably 1 ⁇ m or less.
- the lower limit of the average particle diameter is not particularly limited, but may be 10 nm, for example.
- the “average particle diameter” of the inorganic filler (D) means the median diameter of the inorganic filler (D).
- the median diameter refers to the volume of particles on the larger particle diameter side and the volume of particles on the smaller particle diameter side when the particle size distribution of the powder is divided into two on the basis of a certain particle diameter. Means a particle size that occupies 50% of the total powder.
- the average particle diameter (median diameter) of the inorganic filler (D) is measured by a wet laser diffraction / scattering method.
- the content in the resin composition is such that the underfill material, preferably the pre-applied underfill material, can be bonded while improving the flame resistance of the resin composition and reducing the coefficient of thermal expansion. From the viewpoint of ensuring fluidity at the time, it is preferably 300 parts by mass or less and preferably 200 parts by mass or less with respect to 100 parts by mass of the total amount of the radical polymerizable compound (C) in the resin composition. More preferred. Moreover, it is preferable that content of an inorganic filler (D) shall be 10 mass parts or more with respect to 100 mass parts of total amounts of the radically polymerizable compound (C) in a resin composition, and shall be 20 mass parts or more. More preferably, it is more preferably 50 parts by mass or more. In addition, when using together 2 or more types of inorganic fillers (D), it is preferable that these total amount satisfy
- the flexibility imparting component (E) in the resin composition of the present embodiment is not particularly limited as long as it is a component that can impart flexibility to the layer containing the resin composition.
- polyimide Polyamideimide
- polystyrene polyolefin
- styrene-butadiene rubber SBR
- isoprene rubber IR
- butadiene rubber BR
- acrylonitrile butadiene rubber NBR
- polyurethane polypropylene
- (meth) acryl oligomer acrylonitrile butadiene rubber
- thermoplastic polymer compounds such as silicone resins.
- imparting flexibility Component (E) is preferably at least one selected from the group consisting of (meth) acrylic oligomers and (meth) acrylic polymers.
- Examples of (meth) acrylic oligomers and (meth) acrylic polymers include “ARUFON (registered trademark)” series from Toagosei Co., Ltd., “Act Flow (registered trademark)” series from Soken Chemical Co., Ltd., Negami Kogyo ( "PARACRON (registered trademark)” series of Co., Ltd., and “KURARITY (registered trademark)” series of Kuraray Co., Ltd. are listed.
- the molecular weight of the flexibility-imparting component (E) is not limited, but from the viewpoint of imparting flexibility to the resin composition, the mass average molecular weight is preferably 1,000 or more. From the viewpoint of imparting good toughness, it is more preferably 2,000 or more.
- the resin composition is used as an underfill material, preferably as a pre-applied underfill material, there is no bite of the resin composition in the metal joint portion, and in order to obtain a better and stable shape joint It is preferable to control the melt viscosity of the resin composition to be low and to ensure the fluidity of the resin composition during bonding.
- the mass average molecular weight of the flexibility-imparting component (E) is preferably 1,000,000 or less, more preferably 800,000 or less, still more preferably 100,000 or less, and solvent solubility. In view of the above, 10,000 or less is even more preferable.
- the flexibility-imparting component (E) having a mass average molecular weight in this preferred range the flexibility of the resin composition and bonding when used as an underfill material, preferably a pre-applied underfill material The properties can be balanced with a better balance.
- the content in the resin composition is 100 parts by mass of the total amount of the radical polymerizable compound (C) in the resin composition from the viewpoint of controllability of the melt viscosity. On the other hand, it is preferably 100 parts by mass or less, more preferably 50 parts by mass or less, and still more preferably 30 parts by mass or less.
- the content of the flexibility-imparting component (E) in the resin composition is such that the radicals in the resin composition are more effective and reliable from the viewpoint of the effects obtained by using the flexibility-imparting component (E).
- the resin composition of the present embodiment includes a compound (A) having a phenolic hydroxyl group, a metal ion scavenger (B), and a radical polymerizable compound (C), and if necessary, an inorganic filler (D). And the flexibility provision component (E) and 1 type (s) or 2 or more types of other components may further be included.
- the resin composition of this embodiment may contain a silane coupling agent for the purpose of improving moisture absorption heat resistance and improving the adhesion between the chip and the resin composition.
- the silane coupling agent is not limited as long as it is a silane coupling agent that is generally used for surface treatment of inorganic substances and has low reactivity with the compound (A) having a phenolic hydroxyl group.
- Specific examples thereof include vinylsilane silane coupling agents (eg, vinyltrimethoxysilane, ⁇ - (meth) acryloxypropyltrimethoxysilane), phenylaminosilane silane coupling agents (eg, N-phenyl-3-amino). Propyltrimethoxysilane), phenylsilane-based silane coupling agents, and imidazolesilane-based silane coupling agents. These silane coupling agents can be used alone or in combination of two or more.
- the content in the resin composition is not limited. However, from the viewpoint of improving the moisture absorption heat resistance and reducing the volatilization amount during flip-chip mounting, the content is 0 with respect to 100 parts by mass of the total amount of the radical polymerizable compound (C) in the resin composition. It is preferable that they are 0.05 mass part or more and 20 mass parts or less, and it is more preferable that they are 0.1 mass part or more and 15 mass parts or less. In addition, when using 2 or more types of silane coupling agents together, it is preferable that these total amount exists in the range of the said content.
- the resin composition of the present embodiment may contain a wetting dispersant for the purpose of improving the productivity of the laminate and improving the dispersibility of the inorganic filler (D).
- the wetting and dispersing agent is not limited as long as it is a wetting and dispersing agent generally used in paints. Examples include Disperbyk-110, -111, -180, -161, BYK-W996, -W9010, and -W903 (above product names) manufactured by Big Chemie Japan Co., Ltd. These wet dispersing agents can be used individually by 1 type or in combination of 2 or more types.
- the wetting and dispersing agent When the wetting and dispersing agent is used, its content in the resin composition is not limited, but from the viewpoint of improving the productivity of the laminate, it is 0.1 parts by mass or more with respect to 100 parts by mass of the inorganic filler (D). It is preferably 5 parts by mass or less, and more preferably 0.5 parts by mass or more and 3 parts by mass or less.
- the wetting and dispersing agent When the wetting and dispersing agent is used, its content in the resin composition is not limited, but from the viewpoint of improving the productivity of the laminate, the total amount of the radical polymerizable compound (C) in the resin composition is 100 parts by mass. On the other hand, it is preferably 0.1 parts by mass or more and 5 parts by mass or less, and more preferably 0.5 parts by mass or more and 3 parts by mass. In addition, when using 2 or more types of wet dispersing agents together, it is preferable that these total amount exists in the range of the said content.
- the resin composition of the present embodiment may contain a curing accelerator for the purpose of adjusting the curing speed.
- the curing accelerator is not particularly limited as long as it is known as a curing accelerator for maleimide compounds and is generally used.
- Specific examples of the curing accelerator include imidazoles and derivatives thereof (for example, 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 2,4,5-trimethyl).
- Phenylimidazole tertiary amines (eg, triethylamine, tributylamine), and various organic peroxides (eg, dicumyl peroxide, di (2-tert-butylperoxyisopropyl) benzene as thermal radical polymerization initiators , P-menthane hydroperoxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide).
- tertiary amines eg, triethylamine, tributylamine
- organic peroxides eg, dicumyl peroxide, di (2-tert-butylperoxyisopropyl) benzene as thermal radical polymerization initiators , P-menthane hydroperoxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide.
- the content in the resin composition is not particularly limited, but from the viewpoint of adjusting the curing rate, the total amount of the radical polymerizable compound (C) in the resin composition. It is preferably 0.001 to 3 parts by mass, more preferably 0.005 to 2 parts by mass, more preferably 0.01 to 1 part by mass with respect to 100 parts by mass. More preferably. In addition, when using together 2 or more types of hardening accelerators, it is preferable that these total amount exists in the range of the said content.
- the resin composition of the present embodiment may contain various additives for various purposes within a range where the intended characteristics are not impaired.
- additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, antifoaming agents, leveling agents, brighteners, And flame retardants. These additives can be used individually by 1 type or in combination of 2 or more types.
- the content of the other additives is not particularly limited, but is usually 0.00% relative to 100 parts by mass of the total amount of the radical polymerizable compound (C) in the resin composition. 1 part by mass or more and 10 parts by mass or less.
- the resin composition of this embodiment is prepared from a compound (A) having a phenolic hydroxyl group, a metal ion scavenger (B), and a radical polymerizable compound (C), and if necessary, an inorganic filler ( It is prepared by further mixing D), the flexibility-imparting component (E), and other components. As needed, it is good also as a form of the varnish which melt
- the varnish of the resin composition of the present embodiment can be suitably used as a varnish for producing the laminate of the present embodiment described below.
- the organic solvent is not limited as long as it can suitably dissolve or disperse the above components and does not impair the desired effect of the resin composition of the present embodiment.
- organic solvent examples include alcohols such as methanol, ethanol, and propanol; ketones such as acetone, methyl ethyl ketone (hereinafter sometimes abbreviated as “MEK”), and methyl isobutyl ketone; dimethylacetamide, dimethylformamide, and the like. Amides; aromatic hydrocarbons such as toluene and xylene. These organic solvents can be used alone or in combination of two or more.
- the resin composition of this embodiment is excellent in flux activity, flexibility, and storage stability. Moreover, the laminated body which has a resin layer excellent in flux activity can be provided by apply
- the resin composition of the present embodiment is used as a pre-applied underfill material used in the form of a laminate, it has excellent flux activity, flexibility, and storage stability, and in addition, bondability, moisture absorption heat resistance, and Other suitable effects such as excellent adhesion to the chip can also be exhibited.
- the resin composition of the present embodiment has various excellent characteristics, and in particular, can satisfy both flux activity, flexibility, and storage stability at a high level. It is extremely useful as a pre-applied underfill material.
- a compound having a phenolic hydroxyl group and a metal ion scavenger were used in combination in a solder ball wetting and spreading test, which is an index for evaluating flux activity by the method described in the following examples.
- solder ball wetting and spreading test which is an index for evaluating flux activity by the method described in the following examples.
- a compound having a phenolic hydroxyl group and a metal ion scavenger were sprayed on the glossy surface of the electrolytic copper foil, a solder ball was placed thereon, heated on a hot plate, and the solder was melted on the copper foil. Then, it was cooled at room temperature.
- the flux activity was evaluated by measuring the contact angle of the solder balls with respect to the wetting and spreading of the solder balls to the copper foil.
- the contact angle of the solder ball was determined by obtaining the radius (a) of the solder ball that melted and spread on the copper foil and the height (b) of the solder ball, and calculated the contact angle from the following formula.
- Solder ball contact angle 2 arctan ⁇ (b) / (a) ⁇
- the laminated body of this embodiment is equipped with a support base material and the layer containing the resin composition of this embodiment laminated
- the above-described resin composition of the present embodiment is attached to a support substrate.
- the support substrate is not particularly limited, but a polymer film can be used.
- Examples of the material of the polymer film include polyvinyl chloride, polyvinylidene chloride, polybutene, polybutadiene, polyurethane, ethylene-vinyl oxide copolymer, polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate polyester, polyethylene, polypropylene,
- Examples include a film containing at least one resin selected from the group consisting of ethylene-propylene copolymer, polymethylpentene, polyimide, and polyamide, and a release film in which a release agent is applied to the surface of these films. It is done.
- polyester, polyimide, and polyamide are particularly preferable, and among them, polyethylene terephthalate, which is a kind of polyester, is more preferable.
- the thickness of the support base material of this embodiment is not limited, From the viewpoint of the manufacturability of the laminate, for example, the stability of the coating thickness when the resin composition is applied to the support base material, the thickness is 10 ⁇ m or more and 100 ⁇ m or less. It is preferable. Moreover, it is preferable that the thickness is 10 micrometers or more and 100 micrometers or less also from a viewpoint of the transportability of a resin laminated body.
- the lower limit of the thickness is more preferably 12 ⁇ m or more, still more preferably 25 ⁇ m or more, and even more preferably 30 ⁇ m or more, from the viewpoint of securing the yield when manufacturing a laminate.
- the upper limit of the thickness is 80 ⁇ m or less from the viewpoint of the manufacturing cost of the laminated body because the support base material does not finally exist as a constituent member of the semiconductor device and is peeled off during the process. It is more preferable that
- a method for producing a layered product of the present embodiment by forming a layer containing the resin composition of the present embodiment (hereinafter also simply referred to as “resin composition layer”) on the support substrate, It is not limited.
- a varnish obtained by dissolving or dispersing the resin composition of the present embodiment in an organic solvent is applied to the surface of the support substrate, and dried under heating and / or reduced pressure, And a method of solidifying the resin composition of the present embodiment to form a resin composition layer.
- the drying conditions are not particularly limited, but the content ratio of the organic solvent to the resin composition layer is usually 10% by mass or less, preferably 5% by mass or less with respect to the total amount (100% by mass) of the resin composition layer. Let dry.
- Conditions for achieving such drying also vary depending on the type and blending amount of the organic solvent in the varnish. For example, 30 parts by mass with respect to 100 parts by mass of the total amount in the resin composition containing the compound (A) having a phenolic hydroxyl group, the metal ion scavenger (B), and the radical polymerizable compound (C).
- a varnish containing MEK in an amount of 60 parts by mass or less, drying for about 1 minute or more and 10 minutes or less under a heating condition of 90 ° C. or more and 160 ° C. or less under 1 atmosphere becomes a standard.
- the thickness of the resin composition layer in the laminate of the present embodiment is not limited, the viewpoint of better removing light volatile components during drying of the resin composition layer and the function as the laminate are more effectively and reliably achieved. From the viewpoint, a range of 5 ⁇ m to 500 ⁇ m is preferable, and a range of 10 ⁇ m to 100 ⁇ m is more preferable.
- a semiconductor wafer with a resin composition layer according to the present embodiment includes a semiconductor wafer and the resin composition layer in the laminate laminated on the semiconductor wafer, and is formed from the laminate and the semiconductor wafer according to the embodiment described above. Is done.
- the semiconductor mounting substrate with a resin composition layer according to the present embodiment includes a semiconductor mounting substrate and the resin composition layer in the stacked body stacked on the substrate, and the stacked body and the substrate according to the above described embodiment. Formed from.
- the method for producing the semiconductor wafer with the resin composition layer of the present embodiment is not limited, but for example, the surface of the semiconductor wafer with the electrode formed thereon, that is, the surface to be bonded to the substrate, the laminate of the present embodiment It is obtained by pasting together so that the resin composition layers face each other.
- the method for producing the substrate with the resin composition layer of the present embodiment is not limited.
- the substrate is mounted so that the resin composition layer of the laminate of the present embodiment faces the surface on the chip mounting side of the substrate. It is obtained with.
- a vacuum pressurization type laminator can be used conveniently.
- a method in which the laminate of the present embodiment is pressed through an elastic body such as rubber and bonded is preferable.
- the lamination conditions are not particularly limited as long as conditions that are commonly used in the art, for example, 50 ° C. or higher 140 ° C. temperature below, 1 kgf / cm 2 or more 11 kgf / cm 2 or less in the range of the contact pressure, and 20hPa
- the following atmosphere is performed under reduced pressure.
- the laminated body may be smoothed by hot pressing with a metal plate.
- the laminating step and the smoothing step can be continuously performed by a commercially available vacuum pressurizing laminator. In any case, the laminate attached to the semiconductor wafer or the substrate is removed before the flip chip mounting of the chip.
- the semiconductor device of the present embodiment includes, for example, the semiconductor wafer with the resin composition layer of the present embodiment and / or the substrate with the resin composition layer of the present embodiment, and the resin composition layer, chip, and Consists of a substrate.
- the method for manufacturing the semiconductor device of the present embodiment is not limited.
- the semiconductor wafer with the resin composition layer of the present embodiment is thinned by a grinding means and separated into pieces by a dicing saw, and the resin composition layer is formed.
- a chip is attached and mounted on a substrate.
- a flip chip bonder compatible with the thermocompression bonding method can be preferably used.
- the case where the chip is flip-chip mounted on the substrate is described for convenience, but the target to which the resin composition of the present embodiment is applied is other than the substrate while the chip is flip-chip mounted.
- the resin composition of the present embodiment is a chip laminated body that performs chip-to-chip connection via a junction between a semiconductor wafer and a chip when a chip is mounted on a semiconductor wafer, or TSV (Through Silicon Via).
- the present invention can be used for a joint portion between chips, and in any case, the advantages of the present invention can be obtained.
- Mass average molecular weight (Mw) Using LC-20AD (trade name, manufactured by Shimadzu Corporation), the mass average molecular weight (Mw) was measured as a standard polystyrene equivalent molecular weight by gel permeation chromatography (GPC).
- the flux activity was evaluated by measuring the contact angle of the solder balls with respect to the wetting and spreading of the solder balls to the copper foil.
- the contact angle of the solder ball was determined by using a digital microscope (KH-7700 (trade name), manufactured by Hilox Co., Ltd.), the radius (a) of the solder ball that melted and spread on the copper foil, and the solder ball
- the contact angle was calculated from the following formula.
- Solder ball contact angle 2 arctan ⁇ (b) / (a) ⁇
- a solder ball contact angle of less than 1.60 radians is indicated as A
- a solder ball contact angle of 1.60 radians or more and less than 2.00 radians is indicated as B
- a solder ball contact angle of 2.00 radians or more is indicated as C.
- the contact angle of the solder ball was determined by using a digital microscope (KH-7700 (trade name), manufactured by Hilox Co., Ltd.), the radius (a) of the solder ball that melted and spread on the copper foil, and the solder ball The contact angle was calculated from the following formula.
- Solder ball contact angle 2 arctan ⁇ (b) / (a) ⁇
- a solder ball having a contact angle of less than 1.60 radians is indicated as A, a solder ball having a contact angle of 1.60 radians or more and less than 2.00 radians as B, and a solder ball having a contact angle of 2.00 radians or more as C.
- the flux activity was evaluated by measuring the contact angle of the solder balls with respect to the wetting and spreading of the solder balls to the copper foil.
- the contact angle of the solder ball was determined by using a digital microscope (KH-7700 (trade name), manufactured by Hilox Co., Ltd.), the radius (a) of the solder ball that melted and spread on the copper foil, and the solder ball. The contact angle was calculated from the following formula.
- Solder ball contact angle 2 arctan ⁇ (b) / (a) ⁇
- a solder ball having a contact angle of less than 1.60 radians is described as AA, a solder ball having a contact angle of 1.60 radians or more and less than 2.00 radians, and A having a contact angle of 2.00 radians or more.
- Example 1 As a compound (A) having a phenolic hydroxyl group, PHENOLITE (registered trademark) KA-1163 (trade name, mass average molecular weight (Mw): 4600, softening point: 105 to 115 ° C., 5% mass reduction temperature: 298 ° C., cresol 60 parts by mass (non-volatile content: 50% by mass) of MEK solution of novolac type phenolic resin (manufactured by DIC Corporation) (30 mass parts in terms of non-volatile content), 1- (4-tert--) as the metal ion scavenger (B) 30 parts by mass of butylphenyl) -3- (4-methoxyphenyl) -1,3-propanedione (manufactured by Tokyo Chemical Industry Co., Ltd.), R 1 in the above formula (1) as radically polymerizable compound (C) all hydrogen atom, a maleimide compound n 1 is 1
- Example 2 As the compound (A) having a phenolic hydroxyl group, TBIS (registered trademark) -MP (trade name, 9,9′-bis- (4-hydroxy-3-methylphenyl) fluorene, molecular weight: 378, melting point: 225 ° C., 5% mass reduction temperature: 313 ° C., manufactured by Taoka Chemical Industry Co., Ltd.) Same as Example 1 except that the MEK solution (non-volatile content 50 mass%) was changed to 60 mass parts (30 mass parts in terms of non-volatile content). A varnish was prepared to obtain a resin laminate.
- TBIS registered trademark
- -MP trade name, 9,9′-bis- (4-hydroxy-3-methylphenyl) fluorene, molecular weight: 378, melting point: 225 ° C., 5% mass reduction temperature: 313 ° C., manufactured by Taoka Chemical Industry Co., Ltd.
- Example 3 As a metal ion scavenger (B), (E, E ′)-1,7-bis (4-hydroxy-3-methoxyphenyl) -1,6-heptadiene-3,5-dione (Tokyo Chemical Industry Co., Ltd.) Manufactured) A varnish was prepared in the same manner as in Example 1 except that the amount was changed to 30 parts by mass to obtain a resin laminate.
- Example 4 As the compound (A) having a phenolic hydroxyl group, TBIS (registered trademark) -MP (trade name, 9,9′-bis- (4-hydroxy-3-methylphenyl) fluorene, molecular weight: 378, Taoka Chemical Co., Ltd.
- Example 5 Example 1 except that the compound (A) having a phenolic hydroxyl group was changed to 100 parts by mass (50 parts by mass in terms of nonvolatile content) of a MEK solution of PHENOLITE (registered trademark) KA-1163 (nonvolatile content 50% by mass). A varnish was prepared in the same manner as described above to obtain a resin laminate.
- Example 6 Example 1 was repeated except that the metal ion scavenger (B) was changed to 50 parts by mass of 1- (4-tert-butylphenyl) -3- (4-methoxyphenyl) -1,3-propanedione. A varnish was prepared to obtain a resin laminate.
- Example 7 Except that the metal ion scavenger (B) was changed to 30 parts by mass of 2,4-diamino-6-methyl-1,3,5-triazine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same as in Example 1. A varnish was prepared to obtain a resin laminate.
- Example 8 A varnish was prepared in the same manner as in Example 1 except that the metal ion scavenger (B) was changed to 30 parts by mass of 2,2′-bipyridine (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a resin laminate. It was.
- Example 2 A varnish was prepared in the same manner as in Example 1 except that the metal ion scavenger (B) was not used to obtain a resin laminate.
- Example 3 A varnish was prepared in the same manner as in Example 1 except that the compound (A) having a phenolic hydroxyl group and the metal ion scavenger (B) were not used to obtain a resin laminate.
- Examples 1 to 8 using the resin composition of the present embodiment showed better results in the mounting test than Comparative Examples 1 to 3.
- the resin compositions described in Examples 5 and 6 have no practical problem, but from the results of Examples 5 and 6, in the present embodiment, a resin composition having both excellent flux activity and flexibility is obtained. In order to obtain it, it was shown that the compounding quantity of the compound which has a phenolic hydroxyl group, and a metal ion scavenger needs optimization.
- the resin compositions described in Examples 7 and 8 have no practical problem, but the metal ion scavenger (B) used in Examples 7 and 8 is a maleimide compound formulated as a radical polymerizable compound (C). It was also shown that there was concern about storage stability due to the reactivity. On the other hand, it was also shown that when a diketone derivative was blended as the metal ion scavenger (B), it showed no reactivity with the maleimide compound blended as the radical polymerizable compound (C), and good storage stability was obtained.
- the metal ion scavenger (B) used in Examples 7 and 8 is a maleimide compound formulated as a radical polymerizable compound (C). It was also shown that there was concern about storage stability due to the reactivity. On the other hand, it was also shown that when a diketone derivative was blended as the metal ion scavenger (B), it showed no reactivity with the maleimide compound blended as the radical polymerizable compound
- the resin composition of the present invention is excellent in flux activity, flexibility, and storage stability, and exhibits various effects. Therefore, it is useful as a resin composition, particularly as a pre-applied underfill material. . Since the resin composition of the present invention is excellent in flux activity, when bonding between a semiconductor chip and a substrate, bonding between a semiconductor chip and a semiconductor wafer, and further bonding between a semiconductor chip and a semiconductor chip, good bonding is performed. It is very useful because the state is obtained.
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Abstract
Description
特許文献4でも、意図的にフラックス成分を含まないため、接合部の酸化膜を金属接合前に除去することはできない。
[1]フェノール性水酸基を有する化合物(A)と、金属イオン捕捉剤(B)と、ラジカル重合性化合物(C)と、を含有する、樹脂組成物。
本明細書における「(メタ)アクリロ」とは「アクリロ」及びそれに対応する「メタクリロ」の両方を意味する。「(メタ)アクリル」とは「アクリル」及びそれに対応する「メタクリル」の両方を意味する。「(メタ)アクリレート」とは「アクリレート」及びそれに対応する「メタクリレート」の両方を意味する。
本実施形態の樹脂組成物は、好適にはチップのフリップチップ実装に使用されるアンダーフィル材として用いられる樹脂組成物である。この樹脂組成物は、フェノール性水酸基を有する化合物(A)と、金属イオン捕捉剤(B)と、ラジカル重合性化合物(C)とを含有する。本実施形態の樹脂組成物は、無機充填材(D)及び/又は可撓性付与成分(E)を更に含んでもよい。
フェノール性水酸基を有する化合物(A)は、主に樹脂組成物のフラックス活性に寄与する成分である。
金属イオン捕捉剤(B)としては、金属イオンを捕捉できる化合物であれば特に限定されない。捕捉される金属イオンとしては、特に限定されないが、銅イオンが好ましい。
ラジカル重合性化合物(C)としては、ラジカルにより重合する官能基を有する物質であれば特に限定されないが、例えば、(メタ)アクリレート化合物、マレイミド化合物及びプロペニル化合物が挙げられる。
式(3)中、R3は各々独立に、水素原子又はメチル基を示す。
本実施形態の樹脂組成物は、耐燃性の向上、熱伝導率の向上、及び熱膨張率の低減のため、無機充填材(D)を含有することができる。無機充填材を使用することにより、樹脂組成物などの耐燃性及び熱伝導率を向上させ、熱膨張率を低減することができる。また、無機充填材(D)が電気絶縁性を有すると、本実施形態の樹脂組成物をアンダーフィル材、好ましくはプリアプライドアンダーフィル材の材料として用いた場合、チップの電極間の電気絶縁性をより十分に確保する観点から好ましい。ここで、「電気絶縁性」とは、常温での体積固有抵抗が1012Ω・cm以上であることを意味する。無機充填材(D)の種類としては、特に限定されないが、例えば、溶融シリカ等のシリカ;ベーマイト、水酸化アルミニウム、アルミナ、及び窒化アルミニウム等のアルミニウム化合物;酸化マグネシウム、及び水酸化マグネシウム等のマグネシウム化合物;炭酸カルシウム、及び硫酸カルシウム等のカルシウム化合物;酸化モリブデン、及びモリブデン酸亜鉛等のモリブデン化合物;窒化ホウ素;硫酸バリウム;天然タルク、及び焼成タルク等のタルク;マイカ;短繊維状ガラス、球状ガラス、及び微粉末ガラス(例えば、Eガラス、Tガラス、Dガラス)等のガラスが挙げられる。これらの無機充填材(D)は、1種を単独で又は2種以上を組み合わせて用いることができる。
本実施形態の樹脂組成物における可撓性付与成分(E)は、樹脂組成物を含有する層に対して可撓性を付与できるような成分であれば、特に限定されないが、例えば、ポリイミド、ポリアミドイミド、ポリスチレン、ポリオレフィン、スチレン-ブタジエンゴム(SBR)、イソプレンゴム(IR)、ブタジエンゴム(BR)、アクリロニトリルブタジエンゴム(NBR)、ポリウレタン、ポリプロピレン、(メタ)アクリルオリゴマー、(メタ)アクリルポリマー、及びシリコーン樹脂のような熱可塑性の高分子化合物が挙げられる。これらの可撓性付与成分(E)は、1種を単独で又は2種以上を組み合わせて用いることができる。
本実施形態の樹脂組成物は、フェノール性水酸基を有する化合物(A)と、金属イオン捕捉剤(B)と、ラジカル重合性化合物(C)と含み、必要に応じて、無機充填材(D)と、可撓性付与成分(E)と、その他の成分を1種又は2種以上とを更に含んでいてもよい。
なお、2種以上の湿潤分散剤を併用する場合には、これらの合計量が前記含有量の範囲内であることが好ましい。
本実施形態の積層体、樹脂組成物層付き半導体ウェハ、樹脂組成物層付き半導体搭載用基板、及び半導体装置は、いずれも前記した本実施形態の樹脂組成物を用いて形成される。
本実施形態の積層体は、支持基材と、前記支持基材上に積層された本実施形態の樹脂組成物を含有する層とを備える。このような積層体は、前記した本実施形態の樹脂組成物が、支持基材に添着される。支持基材としては、特に限定されないが、高分子フィルムを使用することができる。高分子フィルムの材質としては、例えば、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリブテン、ポリブタジエン、ポリウレタン、エチレン-酸化ビニル共重合体、ポリエチレンテレフタレート、ポリエチレンナフタレート、及びポリブチレンテレフタレートのポリエステル、ポリエチレン、ポリプロピレン、エチレン-プロピレン共重合体、ポリメチルペンテン、ポリイミド、及びポリアミドからなる群より選ばれる少なくとも1種以上の樹脂を含有するフィルム、並びにこれらのフィルムの表面に離型剤を塗布した離型フィルムが挙げられる。これらの中でも、特にポリエステル、ポリイミド、及びポリアミドが好ましく、その中でもポリエステルの1種である、ポリエチレンテレフタレートがより好ましい。
本実施形態の樹脂組成物層付き半導体ウェハは、半導体ウェハと、その半導体ウェハに積層された前記の積層体における樹脂組成物層とを備え、前記した本実施形態の積層体と半導体ウェハから形成される。本実施形態の樹脂組成物層付き半導体搭載用基板は、半導体搭載用基板と、その基板に積層された前記の積層体における樹脂組成物層とを備え、前記した本実施形態の積層体と基板から形成される。
本実施形態の半導体装置は、例えば、本実施形態の樹脂組成物層付き半導体ウェハ、及び/又は本実施形態の樹脂組成物層付き基板を備え、本実施形態の樹脂組成物層、チップ、及び基板から構成される。本実施形態の半導体装置を製造する方法は、限定されないが、例えば、本実施形態の樹脂組成物層付き半導体ウェハを研削の手段で薄化及びダイシングソーによる個片化を行い、樹脂組成物層付きチップとし、これを基板に搭載する手法が挙げられる。また、本実施形態の樹脂組成物層付き基板に、チップを搭載してもよい。樹脂組成物層付きチップを基板に搭載する方法及び半導体チップを樹脂組成物層付き基板に搭載する方法では、熱圧着工法に対応したフリップチップボンダを好適に使用することができる。また、本実施形態ではチップを基板にフリップチップ実装する場合を便宜的に説明しているが、チップをフリップチップ実装しつつ、本実施形態の樹脂組成物を適用する対象は基板以外とすることも可能である。例えば、本実施形態の樹脂組成物は、半導体ウェハ上へチップを搭載する際の半導体ウェハとチップとの接合部や、TSV(Through Silicon Via)を経由してチップ間接続を行うチップ積層体の、各チップ間の接合部に使用することも可能であり、いずれの場合も本発明による優位性を得ることができる。
(1)質量平均分子量(Mw)
LC-20AD(商品名、(株)島津製作所製)を用いて、ゲルパーミエイションクロマトグラフ(GPC)法により、標準ポリスチレン換算分子量として、質量平均分子量(Mw)を測定した。
フェノール性水酸基を有する化合物を約10mg計量し、TG/DTA6200(商品名、セイコーインスツル(株)製)を用いて、室温から昇温速度10℃/minの条件で500℃まで昇温し、得られた質量減少曲線において、質量が5%減少する温度を5%質量減少温度とした。
フェノール性水酸基を有する化合物単体、金属イオン捕捉剤単体、及びフェノール性水酸基を有する化合物と金属イオン捕捉剤を併用した際のフラックス活性を評価した。
(I)PHENOLITE(登録商標)KA-1163(商品名、クレゾールノボラック型フェノール樹脂、DIC(株)製)
(II)TBIS(登録商標)-MP(商品名、ビスクレゾールフルオレン、田岡化学工業(株)製)
(III)SN-495V(商品名、ナフトールアラルキル型フェノール樹脂、新日鐵化学(株)製)
(IV)BPN01(商品名、プロペニルビフェニレン樹脂、群栄化学工業(株)製)
(V)ELPC75(商品名、フェノール樹脂、群栄化学工業(株)製)
(VI)4,4’-メチレンビス(2,6-ジ-tert-ブチルフェノール)(東京化成工業(株)製)
(i)1-(4-tert-ブチルフェニル)-3-(4-メトキシフェニル)-1,3-プロパンジオン(東京化成工業(株)製)
(ii)(E,E)-1,7-ビス(4-ヒドロキシ-3-メトキシフェニル)-1,6-ヘプタジエン-3,5-ジオン(東京化成工業(株)製)
(iii)2,4-ジアミノ-6-メチル-1,3,5-トリアジン(東京化成工業(株)製)
(iv)2,2’-ビピリジン(東京化成工業(株)製)
(I)~(VI)のフェノール性水酸基を有する化合物を、厚さ12μmの電解銅箔(3EC-III、商品名、三井金属鉱業(株)製)の光沢面に散布し、直径0.5mmのはんだボール(エコソルダー(登録商標)ボールM705(商品名)Sn-3.0Ag-0.5Cu合金、千住金属工業(株)製)を置いた。これを、235℃に保たれたホットプレートの上で1分間加熱し、銅箔上ではんだを溶融させた後、室温で冷却した。はんだボールの銅箔への濡れ広がりをはんだボールの接触角を測定することにより、フラックス活性を評価した。はんだボールの接触角は、デジタルマイクロスコープ(KH-7700(商品名)、(株)ハイロックス製)を用いて、銅箔上に溶融して濡れ広がったはんだボールの半径(a)及びはんだボールの高さ(b)を求め、下記式より接触角を算出した。
はんだボールの接触角が1.60ラジアン未満のものをA、1.60ラジアン以上2.00ラジアン未満のものをB、2.00ラジアン以上のものをCとして記載した。
(i)~(iv)の金属イオン捕捉剤を、厚さ12μmの電解銅箔(3EC-III、商品名、三井金属鉱業(株)製)の光沢面に散布し、直径0.5mmのはんだボール(エコソルダー(登録商標)ボールM705(商品名)、Sn-3.0Ag-0.5Cu合金、千住金属工業(株)製)を置いた。これを、235℃に保たれたホットプレートの上で1分間加熱し、銅箔上ではんだを溶融させた後、室温で冷却した。はんだボールの銅箔への濡れ広がりをはんだボールの接触角を測定することにより、フラックス活性を評価した。はんだボールの接触角は、デジタルマイクロスコープ(KH-7700(商品名)、(株)ハイロックス製)を用いて、銅箔上に溶融して濡れ広がったはんだボールの半径(a)及びはんだボールの高さ(b)を求め、下記式より接触角を算出した。
はんだボールの接触角が1.60ラジアン未満のものをA、1.60ラジアン以上2.00ラジアン未満のものをB、2.00ラジアン以上のものをCとして記載した。
(I)~(VI)のフェノール性水酸基を有する化合物及び(i)~(iv)の金属イオン捕捉剤を、厚さ12μmの電解銅箔(3EC-III、商品名、三井金属鉱業(株)製)の光沢面に散布し、直径0.5mmのはんだボール(エコソルダー(登録商標)ボールM705(商品名)、Sn-3.0Ag-0.5Cu合金、千住金属工業(株)製)を置いた。これを、235℃に保たれたホットプレートの上で1分間加熱し、銅箔上ではんだを溶融させた後、室温で冷却した。はんだボールの銅箔への濡れ広がりをはんだボールの接触角を測定することにより、フラックス活性を評価した。はんだボールの接触角は、デジタルマイクロスコープ(KH-7700(商品名)、(株)ハイロックス製)を用いて、銅箔上に溶融して濡れ広がったはんだボールの半径(a)及びはんだボールの高さ(b)を求め、下記式より接触角を算出した。
はんだボールの接触角が1.60ラジアン未満のものをAA、1.60ラジアン以上2.00ラジアン未満のものをA、2.00ラジアン以上のものをCとして記載した。
(実施例1)
フェノール性水酸基を有する化合物(A)として、PHENOLITE(登録商標)KA-1163(商品名、質量平均分子量(Mw):4600、軟化点:105~115℃、5%質量減少温度:298℃、クレゾールノボラック型フェノール樹脂、DIC(株)製)のMEK溶液(不揮発分50質量%)60質量部(不揮発分換算で30質量部)、金属イオン捕捉剤(B)として、1-(4-tert-ブチルフェニル)-3-(4-メトキシフェニル)-1,3-プロパンジオン(東京化成工業(株)製)30質量部、ラジカル重合性化合物(C)として、前記式(1)におけるR1がすべて水素原子であり、n1が1~3であるマレイミド化合物(BMI-2300、大和化成工業(株)製)のMEK溶液(不揮発分50質量%)40質量部(不揮発分換算で20質量部)、第2のラジカル重合性化合物(C)として、前記式(2)で表され、n2が14(平均値)であるマレイミド化合物(BMI-1000P、ケイ・アイ化成(株)製)のMEK溶液(不揮発分50質量%)40質量部(不揮発分換算で20質量部)、第3のラジカル重合性化合物(C)として、ビス-(3-エチル-5-メチル-4-マレイミドフェニル)メタン(BMI-70、ケイ・アイ化成(株)製)のMEK溶液(不揮発分50質量%)60質量部(不揮発分換算で30質量部)、更に第4のラジカル重合性化合物(C)として、2,2-ビス{4-(4-マレイミドフェノキシ)フェニル}プロパン(BMI-80、ケイ・アイ化成(株)製)のMEK溶液(不揮発分50質量%)60質量部(不揮発分換算で30質量部)、無機充填材(D)として、スラリーシリカ(SC-1050MLQ、平均粒子径:0.3μm、不揮発分60質量%、(株)アドマテックス製)166.7質量部(不揮発分換算で100質量部)、可撓性付与成分(E)として、アクリルポリマー(質量平均分子量(Mw):2900、ARUFON(登録商標)US-6170、東亞合成(株)製)15質量部、イミダゾール系硬化触媒として、1-ベンジル-2-メチルイミダゾール(東京化成工業(株)製)のMEK溶液(不揮発分20質量%)0.5質量部(不揮発分換算で0.1質量部)を混合し、高速攪拌装置を用いて30分間撹拌して、ワニスを得た。このワニスを、表面に離型剤をコートした厚さ38μmのポリエチレンテレフタレートフィルム(TR1-38、ユニチカ(株)製)に塗布し、120℃で5分間加熱乾燥して、本発明の樹脂組成物層の厚さが30μmである樹脂積層体を得た。
フェノール性水酸基を有する化合物(A)として、TBIS(登録商標)-MP(商品名、9,9’-ビス-(4-ヒドロキシ-3-メチルフェニル)フルオレン、分子量:378、融点:225℃、5%質量減少温度:313℃、田岡化学工業(株)製)のMEK溶液(不揮発分50質量%)60質量部(不揮発分換算で30質量部)に変更した以外は、実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
金属イオン捕捉剤(B)として、(E,E’)-1,7-ビス(4-ヒドロキシ-3-メトキシフェニル)-1,6-ヘプタジエン-3,5-ジオン(東京化成工業(株)製)30質量部に変更した以外は、実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
フェノール性水酸基を有する化合物(A)として、TBIS(登録商標)-MP(商品名、9,9’-ビス-(4-ヒドロキシ-3-メチルフェニル)フルオレン、分子量:378、田岡化学工業(株)製)のMEK溶液(不揮発分50質量%)60質量部(不揮発分換算で30質量部)、金属イオン捕捉剤(B)として、(E,E)-1,7-ビス(4-ヒドロキシ-3-メトキシフェニル)-1,6-ヘプタジエン-3,5-ジオン(東京化成工業(株)製)30質量部に変更した以外は、実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
フェノール性水酸基を有する化合物(A)として、PHENOLITE(登録商標)KA-1163のMEK溶液(不揮発分50質量%)100質量部(不揮発分換算で50質量部)に変更した以外は、実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
金属イオン捕捉剤(B)として、1-(4-tert-ブチルフェニル)-3-(4-メトキシフェニル)-1,3-プロパンジオン50質量部に変更した以外は実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
金属イオン捕捉剤(B)として、2,4-ジアミノ-6-メチル-1,3,5-トリアジン(東京化成工業(株)製)30質量部に変更した以外は、実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
金属イオン捕捉剤(B)として、2,2’-ビピリジン(東京化成工業(株)製)30質量部に変更した以外は、実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
フェノール性水酸基を有する化合物(A)を使用しなかった以外は実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
金属イオン捕捉剤(B)を使用しなかった以外は実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
フェノール性水酸基を有する化合物(A)及び金属イオン捕捉剤(B)を使用しなかった以外は実施例1と同様にしてワニスを調製し、樹脂積層体を得た。
(1)実装試験
実施例1~8及び比較例1~3で得られた樹脂積層体を8mm×8mmの正方形に切断し評価用基板上にラミネートした後、フリップチップボンダ(LFB-2301(商品名)、(株)新川製)を用いて、ステージ温度70℃、ボンドヘッド温度300℃、荷重50N、時間8秒の条件で、銅とはんだで構成されるCuピラーを電極に持つ半導体チップを圧着し実装試験を行った。実装試験サンプルの断面観察により、半導体チップ側のCuピラー上のはんだと、基板側の銅配線との接触部に、フラックス活性が発現し合金生成が確認されればAA、フラックス活性が発現せず合金生成が確認されなければCとして記載した。
実施例1~8及び比較例1~3で得られた樹脂積層体を5cm×10cmの短冊状に断裁した後、室温において支持基材のポリエチレンテレフタレートフィルムが内側になるように外径が3cmの金属管に巻き付け、5秒間保持した後巻き戻した。この作業を10回繰り返した後、樹脂組成物層のクラックの有無を目視で確認し、可撓性の評価を行った。クラックの発生が全く認められないものをAA、クラックの発生がわずかに認められるが、実使用上は品質に影響を与えないと思われるレベルをA、クラックが発生し、実使用上許容されないものをCとして記載した。
実施例1~8及び比較例1~3で得られたワニスの粘度(c)を、B型粘度計(東京計器(株)製)を用いて測定し、密閉容器内で2週間室温放置後の粘度(d)を、B型粘度計を用いて再び測定した。下記式にて2週間経過後の粘度の変化率を算出して、変化率が20%未満の場合はAA、2週間経過後の粘度の変化率が20%以上40%未満の場合はA、2週間経過後の粘度の変化率が40%以上の場合はCとして記載した。
粘度の変化率={|(d)-(c)|/(c)}×100
Claims (27)
- フェノール性水酸基を有する化合物(A)と、
金属イオン捕捉剤(B)と、
ラジカル重合性化合物(C)と、
を含有する、樹脂組成物。 - 前記フェノール性水酸基を有する化合物(A)の分子量が、200以上で、かつ、融点が、300℃以下である、請求項1に記載の樹脂組成物。
- 前記フェノール性水酸基を有する化合物(A)における5%質量減少温度が、250℃以上である、請求項1又は2に記載の樹脂組成物。
- 前記金属イオン捕捉剤(B)が、配位原子として窒素及び酸素から選択される少なくとも1種の元素を含有する、請求項1~3のいずれか一項に記載の樹脂組成物。
- 前記金属イオン捕捉剤(B)が、アミン類、アミン誘導体、エーテル誘導体、及びケトン誘導体からなる群より選択される少なくとも1種を含有する、請求項1~4のいずれか一項に記載の樹脂組成物。
- 前記金属イオン捕捉剤(B)が、トリアジン誘導体、ビピリジン誘導体、及びジケトン誘導体からなる群より選択される少なくとも1種を含有する、請求項1~5のいずれか一項に記載の樹脂組成物。
- 前記金属イオン捕捉剤(B)が、1,3-ジケトンを含有する、請求項1~6のいずれか一項に記載の樹脂組成物。
- 前記金属イオン捕捉剤(B)が、2,4-ジアミノ-6-メチル-1,3,5-トリアジン、2,2’-ビピリジン、1,3-ジフェニル-1,3-プロパンジオン、1-(2-メシチレン)-1,3-ブタンジオン、1,3-ビス(4-メトキシフェニル)-1,3-プロパンジオン、1-(4-tert-ブチルフェニル)-3-(4-メトキシフェニル)-1,3-プロパンジオン、及び(E,E)-1,7-ビス(4-ヒドロキシ-3-メトキシフェニル)-1,6-ヘプタジエン-3,5-ジオンからなる群より選択される少なくとも1種を含有する、請求項1~6のいずれか一項に記載の樹脂組成物。
- 前記金属イオン捕捉剤(B)が、1-(4-tert-ブチルフェニル)-3-(4-メトキシフェニル)-1,3-プロパンジオン、及び(E,E)-1,7-ビス(4-ヒドロキシ-3-メトキシフェニル)-1,6-ヘプタジエン-3,5-ジオンからなる群より選択される少なくとも1種を含有する、請求項1~8のいずれか一項に記載の樹脂組成物。
- 前記ラジカル重合性化合物(C)が、(メタ)アクリレート化合物、マレイミド化合物、及びプロペニル化合物からなる群より選択される少なくとも1種を含有する、請求項1~9のいずれか一項に記載の樹脂組成物。
- 前記ラジカル重合性化合物(C)が、2,2’-ビス{4-(4-マレイミドフェノキシ)フェニル}プロパン、1,2-ビス(マレイミド)エタン、1,4-ビス(マレイミド)ブタン、1,6-ビス(マレイミド)ヘキサン、N,N’-1,3-フェニレンジマレイミド、N,N’-1,4-フェニレンジマレイミド、N-フェニルマレイミド、下記式(1)で表されるマレイミド化合物、下記式(2)で表されるマレイミド化合物、及び下記式(3)で表されるマレイミド化合物からなる群より選択される少なくとも1種を含有する、請求項10に記載の樹脂組成物。
- 前記ラジカル重合性化合物(C)が、2,2’-ビス{4-(4-マレイミドフェノキシ)フェニル}プロパン、前記式(1)で表されるマレイミド化合物、前記式(2)で表されるマレイミド化合物、及び前記式(3)で表されるマレイミド化合物からなる群より選択される少なくとも1種のマレイミド化合物を含有する、請求項11に記載の樹脂組成物。
- 前記樹脂組成物中における前記フェノール性水酸基を有する化合物(A)の含有量が、前記樹脂組成物中における前記ラジカル重合性化合物(C)の合計量100質量部に対して、5質量部以上50質量部以下である、請求項1~12のいずれか一項に記載の樹脂組成物。
- 前記樹脂組成物中における前記金属イオン捕捉剤(B)の含有量が、前記樹脂組成物中における前記ラジカル重合性化合物(C)の合計量100質量部に対して、5質量部以上50質量部以下である、請求項1~13のいずれか一項に記載の樹脂組成物。
- 無機充填材(D)を更に含有する、請求項1~14のいずれか一項に記載の樹脂組成物。
- 前記無機充填材(D)が、電気絶縁性を有する、請求項15に記載の樹脂組成物。
- 前記無機充填材(D)の平均粒子径が、3μm以下である、請求項15又は16に記載の樹脂組成物。
- 前記無機充填材(D)が、シリカ、水酸化アルミニウム、アルミナ、ベーマイト、窒化ホウ素、窒化アルミニウム、酸化マグネシウム、及び水酸化マグネシウムからなる群より選択される少なくとも1種を含有する、請求項15~17のいずれか一項に記載の樹脂組成物。
- 前記樹脂組成物中における前記無機充填材(D)の含有量が、前記ラジカル重合性化合物(C)の合計量100質量部に対して、300質量部以下である、請求項15~18のいずれか一項に記載の樹脂組成物。
- 可撓性付与成分(E)を更に含有する、請求項1~19のいずれか一項に記載の樹脂組成物。
- 前記可撓性付与成分(E)が、熱可塑性の高分子化合物を含有し、前記高分子化合物の質量平均分子量が、1,000以上1,000,000以下である、請求項20に記載の樹脂組成物。
- 前記可撓性付与成分(E)が、(メタ)アクリルオリゴマー及び(メタ)アクリルポリマーからなる群より選択される少なくとも1種を含有する、請求項20又は21に記載の樹脂組成物。
- プリアプライドアンダーフィル材用である、請求項1~22のいずれか一項に記載の樹脂組成物。
- 支持基材と、
前記支持基材上に積層された請求項1~23のいずれか一項に記載の樹脂組成物を含有する層と、
を備える、積層体。 - 半導体ウェハと、
前記半導体ウェハに積層された請求項24に記載の積層体と、を備え、
前記樹脂組成物を含有する層が、前記半導体ウェハに積層された、
樹脂組成物層付き半導体ウェハ。 - 半導体搭載用基板と、
前記半導体搭載用基板に積層された請求項24に記載の積層体と、を備え、
前記樹脂組成物を含有する層が、前記半導体搭載用基板に積層された、
樹脂組成物層付き半導体搭載用基板。 - 請求項25に記載の樹脂組成物層付き半導体ウェハ、及び/又は、請求項26に記載の樹脂組成物層付き半導体搭載用基板を備える、半導体装置。
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CN112004845A (zh) | 2020-11-27 |
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