JP5559999B2 - 光硬化性樹脂組成物 - Google Patents
光硬化性樹脂組成物 Download PDFInfo
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- JP5559999B2 JP5559999B2 JP2009170136A JP2009170136A JP5559999B2 JP 5559999 B2 JP5559999 B2 JP 5559999B2 JP 2009170136 A JP2009170136 A JP 2009170136A JP 2009170136 A JP2009170136 A JP 2009170136A JP 5559999 B2 JP5559999 B2 JP 5559999B2
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- 239000011342 resin composition Substances 0.000 title claims description 61
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- 239000011347 resin Substances 0.000 claims description 70
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
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- 238000006243 chemical reaction Methods 0.000 claims description 24
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- 238000001035 drying Methods 0.000 claims description 17
- 238000000016 photochemical curing Methods 0.000 claims description 5
- 238000001723 curing Methods 0.000 claims description 4
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- 239000000049 pigment Substances 0.000 description 93
- 239000010408 film Substances 0.000 description 55
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- 125000000217 alkyl group Chemical group 0.000 description 39
- 239000003822 epoxy resin Substances 0.000 description 38
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 36
- 239000000126 substance Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
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- 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 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 11
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 8
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- 238000013508 migration Methods 0.000 description 8
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- 238000007747 plating Methods 0.000 description 8
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 239000013039 cover film Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000009413 insulation Methods 0.000 description 6
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 5
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- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 4
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
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- 150000004053 quinones Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000001062 red colorant Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Description
この光硬化性樹脂組成物には溶剤現像型とアルカリ現像型があるが、近年では、環境対策の点から希薄な弱アルカリ水溶液で現像できるアルカリ現像型が主流になっている。例えば、プリント配線基板製造、液晶表示板製造、あるいは印刷製版等において、アルカリ現像型の光硬化性樹脂組成物が用いられている。例えば、プリント配線板製造においてソルダーレジストとして使用される際、その硬化物において半田付け等、高温条件での処理に耐え得る耐熱性や、耐水性、耐湿性等の長期信頼性に関わる特性が求められる。
このような構成により、吸湿性を抑え、その硬化物において、プリント配線板等に用いられる際に、耐マイグレーション特性を損なうことなく冷熱サイクル耐性を向上させることが可能となる。
このような光重合開始剤を用いることにより、高濃度で顔料を有するレジストにおいて高解像を得ることができる。
このような硬化物において、プリント配線板等に用いられる際に、耐マイグレーション特性を損なうことなく冷熱サイクル耐性を向上させることが可能となる。
このようなプリント配線板において、耐マイグレーション特性を損なうことなく冷熱サイクル耐性を向上させることが可能となる。
先ず、本実施形態の光硬化性樹脂組成物を構成するカルボキシル基含有樹脂としては、アルカリ現像性を付与する目的で、分子中にカルボキシル基を有している公知の各種カルボキシル基含有樹脂を使用することができる。特に、分子中にエチレン性不飽和二重結合を有するカルボキシル基含有感光性樹脂が、光硬化性や耐現像性の面からより好ましい。そして、その不飽和二重結合は、アクリル酸もしくはメタアクリル酸又はそれらの誘導体由来のものが好ましい。
(1)(メタ)アクリル酸等の不飽和カルボン酸と、スチレン、α−メチルスチレン、低級アルキル(メタ)アクリレート、イソブチレン等の不飽和基含有化合物との共重合により得られるカルボキシル基含有樹脂。
(2)脂肪族ジイソシアネート、分岐脂肪族ジイソシアネート、脂環式ジイソシアネート、芳香族ジイソシアネート等のジイソシアネートと、ジメチロールプロピオン酸、ジメチロールブタン酸等のカルボキシル基含有ジアルコール化合物及びポリカーボネート系ポリオール、ポリエーテル系ポリオール、ポリエステル系ポリオール、ポリオレフィン系ポリオール、アクリル系ポリオール、ビスフェノールA系アルキレンオキシド付加体ジオール、フェノール性ヒドロキシル基及びアルコール性ヒドロキシル基を有する化合物等のジオール化合物の重付加反応によるカルボキシル基含有ウレタン樹脂。
(3)ジイソシアネートと、ビスフェノールA型エポキシ樹脂、水添ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ビキシレノール型エポキシ樹脂、ビフェノール型エポキシ樹脂等の2官能エポキシ樹脂の(メタ)アクリレートもしくはその部分酸無水物変性物、カルボキシル基含有ジアルコール化合物及びジオール化合物の重付加反応による感光性カルボキシル基含有ウレタン樹脂。
(4)上述した(2)又は(3)の樹脂の合成中に、ヒドロキシアルキル(メタ)アクリレート等の分子内に1つの水酸基と1つ以上の(メタ)アクリル基を有する化合物を加え、末端(メタ)アクリル化した感光性カルボキシル基含有ウレタン樹脂。
(5)上述した(2)又は(3)の樹脂の合成中に、イソホロンジイソシアネートとペンタエリスリトールトリアクリレートの等モル反応物など、分子内に1つのイソシアネート基と1つ以上の(メタ)アクリル基を有する化合物を加え末端(メタ)アクリル化した感光性カルボキシル基含有ウレタン樹脂。
(6)後述するような2官能又はそれ以上の多官能(固形)エポキシ樹脂に(メタ)アクリル酸を反応させ、側鎖に存在する水酸基に2塩基酸無水物を付加させた感光性カルボキシル基含有樹脂。
(7)後述するような2官能(固形)エポキシ樹脂の水酸基をさらにエピクロロヒドリンでエポキシ化した多官能エポキシ樹脂に(メタ)アクリル酸を反応させ、生じた水酸基に2塩基酸無水物を付加させた感光性カルボキシル基含有樹脂。
(8)後述するような2官能オキセタン樹脂にジカルボン酸を反応させ、生じた1級の水酸基に2塩基酸無水物を付加させたカルボキシル基含有ポリエステル樹脂。
(9)1分子中に2個以上のフェノール性水酸基を有する化合物とエチレンオキサイド、プロピレンオキサイドなどのアルキレンオキサイドとを反応させて得られる反応生成物に不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られるカルボキシル基含有感光性樹脂。
(10)1分子中に2個以上のフェノール性水酸基を有する化合物とエチレンカーボネート、プロピレンカーボネートなどの環状カーボネート化合物とを反応させて得られる反応生成物に不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られるカルボキシル基含有感光性樹脂
(11)上述した(1)〜(10)の樹脂にさらに1分子内に1つのエポキシ基と1つ以上の(メタ)アクリル基を有する化合物を付加してなる感光性カルボキシル基含有樹脂。
これらカルボキシル基含有樹脂は、列挙したものに限らず使用することができ、1種類でも複数種混合しても使用することができる。
モノアゾ系:Pigment Red 1, 2, 3, 4, 5, 6, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 112, 114, 146, 147, 151, 170, 184, 187, 188, 193, 210, 245, 253, 258, 266, 267, 268, 269
ジスアゾ系:Pigment Red 37, 38, 41
モノアゾレーキ系:Pigment Red 48:1, 48:2, 48:3, 48:4, 49:1, 49:2, 50:1, 52:1, 52:2, 53:1, 53:2, 57:1, 58:4, 63:1, 63:2, 64:1,68
ベンズイミダゾロン系:Pigment Red 171、Pigment Red 175、Pigment Red 176、Pigment Red 185、Pigment Red 208
ぺリレン系:Solvent Red 135、Solvent Red 179、Pigment Red 123、Pigment Red 149、Pigment Red 166、Pigment Red 178、Pigment Red 179、Pigment Red 190、Pigment Red 194、Pigment Red 224
ジケトピロロピロール系:Pigment Red 254、Pigment Red 255、Pigment Red 264、Pigment Red 270、Pigment Red 272
縮合アゾ系:Pigment Red 220、Pigment Red 144、Pigment Red 166、Pigment Red 214、Pigment Red 220、Pigment Red 221、Pigment Red 242
アンスラキノン系:Pigment Red 168、Pigment Red 177、Pigment Red 216、Solvent Red 149、Solvent Red 150、Solvent Red 52、Solvent Red 207
キナクリドン系:Pigment Red 122、Pigment Red 202、Pigment Red 206、Pigment Red 207、Pigment Red 209
アントラキノン系:Solvent Yellow 163、Pigment Yellow 24、Pigment Yellow 108、Pigment Yellow 193、Pigment Yellow 147、Pigment Yellow 199、Pigment Yellow 202。
イソインドリノン系:Pigment Yellow 110、Pigment Yellow 109、Pigment Yellow 139、Pigment Yellow 179、Pigment Yellow 185。
縮合アゾ系:Pigment Yellow 93、Pigment Yellow 94、Pigment Yellow 95、Pigment Yellow 128、Pigment Yellow 155、Pigment Yellow 166、Pigment Yellow 180。
ベンズイミダゾロン系:Pigment Yellow 120、Pigment Yellow 151、Pigment Yellow 154、Pigment Yellow 156、Pigment Yellow 175、Pigment Yellow 181。
モノアゾ系:Pigment Yellow 1, 2, 3, 4, 5, 6, 9, 10, 12, 61, 62, 62:1, 65, 73, 74, 75, 97, 100, 104, 105, 111, 116, 167, 168, 169, 182, 183。
ジスアゾ系:Pigment Yellow 12, 13, 14, 16, 17, 55, 63, 81, 83, 87, 126, 127, 152, 170, 172, 174, 176, 188, 198。
過酸化物分解剤は市販のものであってもよく、例えば、アデカスタブTPP(旭電化社製)、マークAO−412S(アデカ・アーガス化学社製)、スミライザー(登録商標)TPS(住友化学社製)等が挙げられる。これら酸化防止剤は、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。
温度計、窒素導入装置兼アルキレンオキサイド導入装置及び撹拌装置を備えたオートクレーブに、ノボラック型クレゾール樹脂(昭和高分子(株)製、商品名「ショーノールCRG951」、OH当量:119.4)119.4g、水酸化カリウム1.19g及びトルエン119.4gを仕込み、撹拌しつつ系内を窒素置換し、加熱昇温した。
ジエチレングリコールモノエチルエーテルアセテート600gにオルソクレゾールノボラック型エポキシ樹脂〔大日本インキ化学工業株式会社製、EPICLON N−695、軟化点95℃、エポキシ当量214、平均官能基数7.6〕1070g(グリシジル基数(芳香環総数):5.0モル)、アクリル酸360g(5.0モル)、及びハイドロキノン1.5gを仕込み、100℃に加熱攪拌し、均一溶解した。
*1:ZFR-1401H(固形分:65.0%、固形分酸価:100日本化薬社製)
*2:ZCR-1601H(固形分:65.0%、固形分酸価:100日本化薬社製)
*3:2-メチル-1-(4-メチルチオフェニル)-2-モルフォリノプロパン-1-オン(チバ・スペシャルティ・ケミカルズ社製 IRGACURE907)
*4: エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]1,1-(O-アセチルオキシム)(チバ・スペシャルティ・ケミカルズ社製 IRGACURE OXE02)
*5:ビスフェノールAとハロゲン化メチルスチレンとの縮合反応により得られる化合物(昭和高分子社製:リポキシBPV-1X)
*6:末端スチレンのオリゴフェニレンエーテル化合物(三菱ガス化学社製)
*7:ビスマレイミド化合物(DIC社製 MIA-200)
*8:4,4’-ジフェニルメタンビスマレイミド(大和化成工業社製 BMI-1000H)
*9:3,3’-ジメチル-5,5’-ジエチル-4,4’-ジフェニルメタンビスマレイミド(大和化成工業社製 BMI-5100)
*10:1,6-ビスマレイミド-(2,2,4-トリメチル)ヘキサン(大和化成工業社製 BMI-TMH)
*11:2,4,6-トリメルカプト-s-トリアジン(三協化成社製 ジスネット F
*12:1,4-ビス(3-メルカプトブチリルオキシ)ブタン(昭和電工社製 カレンズ MTBD1)
*13:2−メルカプトベンゾチアゾール(川口化学工業社製 アクセル M)
*14:ポリブタジエン骨格エポキシ樹脂(ダイセル化学社製 PB3600)
*15:ビスフェノール型エポキシ樹脂(東都化成社製 YSLV-80XY)
*16:ブロックイソシアネート(旭化成ケミカルズ社製 TPA-B80E)
*17:メチル化メラミン樹脂(三和ケミカル社製 Mw-100LM)
*18:酸化防止剤(チバ・スペシャルティ・ケミカルズ社製)
*19:ジペンタエリスリトールヘキサアクリレート(日本化薬社製)
*20:B−30(堺化学社製)
*21:C.I.Pigment Blue 15:3
*22:C.I.Pigment Yellow 147
*23:ジプロピレングリコールモノメチルエーテル
<最適露光量>
表1に記載の各実施例及び比較例の組成物を、バフロール研磨後、水洗し、乾燥させた銅厚35μmの回路パターン基板に、それぞれスクリーン印刷法により全面に塗布し、80℃の熱風循環式乾燥炉で60分間乾燥させた。
乾燥後、高圧水銀灯(ショートアークランプ)搭載の露光装置を用いてステップタブレット(Kodak No.2)を介して露光し、現像(30℃、0.2MPa、1wt%Na2CO3水溶液)を60秒で行った際残存するステップタブレットのパターンが7段の時を最適露光量とした。
表1に記載の実施例及び比較例の組成物を、銅ベタ基板上にスクリーン印刷法により乾燥後、約25μmになるように塗布し、80℃の熱風循環式乾燥炉で30分間乾燥させた。乾燥後、1質量%炭酸ナトリウム水溶液によって現像を行い、乾燥塗膜が除去されるまでの時間をストップウォッチにより計測した。
表1に記載の各実施例及び比較例の組成物を、パターン形成された銅箔基板上にスクリーン印刷で乾燥後の膜厚が20μmになるように全面塗布し、80℃で30分乾燥し、室温まで放冷する。この基板に高圧水銀灯(ショートアークランプ)搭載の露光装置を用いて最適露光量でソルダーレジストパターンを露光し、30℃の1wt%Na2CO3水溶液をスプレー圧2kg/cm2の条件で60秒間現像を行い、レジストパターンを得た。
市販品の無電解ニッケルめっき浴及び無電解金めっき浴を用いて、ニッケル0.5μm、金0.03μmの条件でめっきを行い、テープピールにより、レジスト層の剥がれの有無やめっきのしみ込みの有無を評価した後、テープピールによりレジスト層の剥がれの有無を評価した。判定基準は以下のとおりである。
◎:染み込み、剥がれが見られない
○:めっき後に少し染み込みが確認されるが、テープピール後は剥がれない
△:めっき後にほんの僅かしみ込みが見られ、テープピール後に剥がれも見られる
×:めっき後に剥がれが有る
表1に記載の各実施例及び比較例の組成物を、クシ型電極(ライン/スペース=50μm/50μm)が形成された基板に塗布し、露光・現像した後、熱硬化して、評価基板を作製した。この評価基板を、130℃、湿度85%の雰囲気下の高温高湿槽に入れ、電圧5Vを荷電し、192時間、HAST(Highly Accelerated Stress Test)を行った。HAST後の電気絶縁性を測定した。
表1に記載の各実施例及び比較例の組成物を、2mmの銅ラインパターンが形成された基板に塗布し、露光・現像した後、熱硬化して、銅ライン上に3mm角のレジストパターンが形成された評価基板を作製した。この評価基板を、−65℃と150℃の間で温度サイクルが行われる冷熱サイクル機に入れ、TCT(Thermal Cycle Test)を行った。そして、600サイクル時、800サイクル時および1000サイクル時の外観を観察した。
◎:1000サイクルで異常なし
○:800サイクルで異常なし、1000サイクルでクラック発生
△:600サイクルで異常なし、800サイクルでクラック発生
×:600サイクルでクラック発生
表1に記載の各実施例及び比較例の組成物の硬化物(硬化皮膜)を形成した評価基板を、PCT装置(エスペック株式会社製 HAST SYSTEM TPC−412MD)を用いて、121℃、飽和、0.2MPaの条件で、168、192時間PCT(Pressure Cooker Test)を行った。そして、処理後の塗膜の状態を評価した。判定基準は以下の通りである。
◎:192時間膨れ、剥がれ、変色、溶出のないもの
○:168時間膨れ、剥がれ、変色、溶出のないもの
△:若干の膨れ、剥がれ、変色、溶出があるもの
×:膨れ、剥がれ、変色、溶出が多く見られるもの
実施例1及び比較例1の感光性樹脂組成物を、以下に示す方法にて評価基板を作成し、同様に評価を行った。
実施例1及び比較例1の光硬化性樹脂組成物を、それぞれメチルエチルケトンで適宜希釈した後、アプリケーターを用いて、乾燥後の膜厚が20μmになるようにPETフィルム(東レ製 FB−50:16μm)に塗布し、80℃で30分乾燥させドライフィルムを得た。
回路形成された基板をバフ研磨した後、上記方法にて作製したドライフィルムを、真空ラミネーター(名機製作所製 MVLP(登録商標)−500)を用いて加圧度:0.8MPa、70℃、1分、真空度:133.3Paの条件で加熱ラミネートして、未露光のソルダーレジスト層を有する基板(未露光の基板)を得た。
評価結果を表2に示す。
Claims (5)
- カルボキシル基含有樹脂、光重合開始剤、ビニルフェニル基含有化合物、及びマレイミド化合物を含む光硬化性樹脂組成物であって、
前記ビニルフェニル基含有化合物は、前記マレイミド化合物と硬化反応することを特徴とする光硬化性樹脂組成物。 - さらにメルカプト化合物を含むことを特徴とする請求項1に記載の光硬化性樹脂組成物。
- 請求項1または2に記載の光硬化性樹脂組成物を、フィルムに塗布・乾燥して得られることを特徴とするドライフィルム。
- 請求項1または2に記載の光硬化性樹脂組成物を基材に塗布・乾燥して得られる乾燥塗膜、または前記光硬化性樹脂組成物をフィルムに塗布・乾燥して得られるドライフィルムを基材にラミネートして得られる塗膜を、活性エネルギー線の照射により光硬化させて得られることを特徴とする硬化物。
- 請求項1または2に記載の光硬化性樹脂組成物を基材に塗布・乾燥して得られる乾燥塗膜、または前記光硬化性樹脂組成物をフィルムに塗布・乾燥して得られるドライフィルムを基材にラミネートして得られる塗膜を、活性エネルギー線の照射により光硬化させて得られる硬化物のパターンを有することを特徴とするプリント配線板。
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