JP4315892B2 - 感光性樹脂組成物、およびこれを用いた感光性ドライフィルム - Google Patents
感光性樹脂組成物、およびこれを用いた感光性ドライフィルム Download PDFInfo
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- JP4315892B2 JP4315892B2 JP2004340886A JP2004340886A JP4315892B2 JP 4315892 B2 JP4315892 B2 JP 4315892B2 JP 2004340886 A JP2004340886 A JP 2004340886A JP 2004340886 A JP2004340886 A JP 2004340886A JP 4315892 B2 JP4315892 B2 JP 4315892B2
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- photosensitive resin
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- compound
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- 239000011342 resin composition Substances 0.000 title claims abstract description 48
- 229920005989 resin Polymers 0.000 claims abstract description 56
- 239000011347 resin Substances 0.000 claims abstract description 56
- -1 thiol compound Chemical class 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000003999 initiator Substances 0.000 claims abstract description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 60
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 claims description 6
- 238000013329 compounding Methods 0.000 claims description 6
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 5
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 abstract description 31
- 238000007747 plating Methods 0.000 abstract description 25
- 239000003505 polymerization initiator Substances 0.000 abstract 1
- 238000010186 staining Methods 0.000 abstract 1
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- 238000011156 evaluation Methods 0.000 description 17
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- 238000004519 manufacturing process Methods 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 9
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- 239000007864 aqueous solution Substances 0.000 description 8
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 238000011161 development Methods 0.000 description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- NOEMSRWQFGPZQS-UHFFFAOYSA-N CCC(O)=S.CCC(O)=S.CCC(O)=S.CCC(CO)(CO)CO Chemical compound CCC(O)=S.CCC(O)=S.CCC(O)=S.CCC(CO)(CO)CO NOEMSRWQFGPZQS-UHFFFAOYSA-N 0.000 description 5
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 229910000679 solder Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- IHUNBGSDBOWDMA-AQFIFDHZSA-N all-trans-acitretin Chemical compound COC1=CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1C IHUNBGSDBOWDMA-AQFIFDHZSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- BJFHJALOWQJJSQ-UHFFFAOYSA-N (3-methoxy-3-methylpentyl) acetate Chemical compound CCC(C)(OC)CCOC(C)=O BJFHJALOWQJJSQ-UHFFFAOYSA-N 0.000 description 2
- FPHMCZHPLGNARL-UHFFFAOYSA-N (4-methylnaphthalen-1-yl)oxyboronic acid Chemical compound C1=CC=C2C(C)=CC=C(OB(O)O)C2=C1 FPHMCZHPLGNARL-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- NSWNXQGJAPQOID-UHFFFAOYSA-N 2-(2-chlorophenyl)-4,5-diphenyl-1h-imidazole Chemical class ClC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 NSWNXQGJAPQOID-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- RFMXKZGZSGFZES-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OC(=O)CS.CCC(CO)(CO)CO RFMXKZGZSGFZES-UHFFFAOYSA-N 0.000 description 2
- NYBXFCLDEATPCM-UHFFFAOYSA-N 3-methyloxetan-2-one Chemical compound CC1COC1=O NYBXFCLDEATPCM-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
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- OHJIOAVILUZUIT-UHFFFAOYSA-N O-(1-hydroxybutyl) propanethioate Chemical compound CCCC(O)OC(=S)CC OHJIOAVILUZUIT-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- LMGYOBQJBQAZKC-UHFFFAOYSA-N 1-(2-ethylphenyl)-2-hydroxy-2-phenylethanone Chemical compound CCC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 LMGYOBQJBQAZKC-UHFFFAOYSA-N 0.000 description 1
- RSZHBVPYGJXEGF-UHFFFAOYSA-N 1-(2-sulfanylacetyl)oxybutyl 2-sulfanylacetate Chemical compound SCC(=O)OC(CCC)OC(=O)CS RSZHBVPYGJXEGF-UHFFFAOYSA-N 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
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- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 239000000057 synthetic resin Substances 0.000 description 1
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- 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
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- 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
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Photometry And Measurement Of Optical Pulse Characteristics (AREA)
Description
上述のように、本発明の感光性樹脂組成物は、アルカリ可溶性樹脂(A)と、光重合性化合物(B)と、光重合開始剤(C)とを少なくとも有してなる感光性樹脂組成物において、上記光重合開始剤(C)は、少なくとも必須成分としてヘキサアリールビスイミダゾール系化合物(C1)と多官能チオール化合物(C2)とを含むことを特徴とするものである。
本発明の感光性樹脂組成物に使用されるアルカリ可溶性樹脂(A)(以下、(A)成分という。)としては、例えば、(メタ)アクリル系樹脂、スチレン系樹脂、エポキシ系樹脂、アミド系樹脂、アミドエポキシ系樹脂、アルキド系樹脂、フェノール系樹脂、フェノールノボラック系樹脂、クレゾールノボラック系樹脂等が挙げられる。アルカリ現像性の点からは(メタ)アクリル系樹脂が好ましい。
本発明に用いられる光重合性化合物(B)(以下、(B)成分という。)は、分子内に少なくとも1つの重合可能なエチレン性不飽和基を有することを特徴とする。(B)成分の配合量は,(A)成分の固形部100質量部に対して10〜200質量部、好ましくは30〜150質量部、より好ましくは50〜120質量部である。
本発明に用いられる光重合開始剤(C)(以下、(C)成分という。)は、少なくとも必須成分としてヘキサアリールビスイミダゾール系化合物(C1)と多官能チオール化合物(C2)とを含むことを特徴とする。ヘキサアリールビスイミダゾール系化合物(C1)を有することにより、特に密着性、解像性に優れた効果を奏することができる。
本発明では、上記成分の他に粘度調整などの目的のために必要に応じて、アルコール類、ケトン類、酢酸エステル類、グリコールエーテル類、グリコールエーテルエステル類、石油系溶剤などの希釈用の有機溶剤を適宜加えることができる。
次に、本発明の感光性ドライフィルムについて説明する。本発明の感光性ドライフィルムは、少なくとも支持フィルム上に上記感光性樹脂組成物から形成された感光性樹脂層を設けたものである。その使用にあたっては、被処理体(基板)の上に露出した感光性樹脂層を重ねた後、感光性樹脂層から支持フィルムを剥離することによって、被処理体(基板)上に感光性樹脂層を容易に設けることができる。
下記表1に示す組成により化合物を攪拌混合して感光性樹脂組成物溶液を調整した。なお、表中の(A)、(B)、(C)は以下の化合物を表す。また、表1に記載の成分以外にはメチルエチルケトンを60質量部用いた。
メチルメタクリレート:メタクリル酸:スチレンを質量比50:25:25の割合で共重合させた質量平均分子量8万の樹脂を固形分換算で100質量部使用した。
(B)光重合性化合物
(B−1)
[1]:ポリプロピレングリコールジアクリレート(n;12)「アロニックスM270」(商品名、東亜合成株式会社製)
[2]:エトキシ化ポリプロピレングリコールジメタクリレート「アロニックスM775」(商品名、東亜合成株式会社製)
(B−2):2.2−ビス〔4−(メタクロキシ・ポリエトキシ)フェニル〕プロパン「BPE500」(商品名、新中村化学工業株式会社製)
(C)光重合開始剤
(C1−1):2.2−ビス(2−クロロフェニル)−4.5.4.5−テトラフェニル−1.2−ビイミダゾール「B−CIM」(商品名、保土ヶ谷化学工業株式会社製)
(C1−2):2,2−ビス(2,6−ジクロロフェニル)−4.5.4'.5'−テトラフェニル−1.2−ビイミダゾール「TC−HABI」(商品名、日本シーベルヘグナー株式会社製)
(C2−1):トリメチロールプロパントリスチオプロピオネート(TMMP)(堺化学工業株式会社製)
(C2−2):ペンタエリスリトールテトラキスチオグリコール(PEMP)(堺化学工業株式会社製)
(C3):n−フェニルグリシン(三井化学株式会社製)
(C4):テトラ−n−ブチルアンモニウム・ブチルトリ(4−メチル−1−ナフチル)ボレイト
(C5):9−フェニルアクリジン
なお、以下特に記載していない場合、現像は、30℃で1質量%Na2CO3水溶液をスプレー圧1.2kg/cm2で40秒間スプレーすることにより行なった。
上記方法にてラミネートした感光性ドライフィルム上に、ストファー21段ステップタブレットを露光マスクとして置き、露光量10mJ/cm2で露光後、現像をおこない、残った密着/解像(ライン&スペース)パターンの最小寸法を評価した。なお、露光装置は、「DP−100」(商品名、オルボテック社製)を使用した。
上記方法にて感光性ドライフィルムをラミネート後、黄色灯「FLR40SY−F/M」(商品名、日立製、40W×2)下で放置し、0、2、4、6、8時間後の感度、密着/解像の変化について評価を行なった。基板と黄色灯との間の距離は、50cmで行なった。また、放置環境は、東京応化工業株式会社内クリーンルーム内、黄色灯下50cm、室温20℃、湿度50%とした。
テント基板(スルホール径:直径6.0mm)をバフ研摩後、感光性ドライフィルムを両面ラミネートした。その後、両面露光(露光量:10mJ/cm2)を行ない、現像(40秒)後、テンシロン万能試験機(株式会社オリエンテック社製、圧縮試験スキャンスピード:20mm/min、ヘッド径φ2mm)を用いて膜破断時のレジスト膜強度を測定した。
上記方法にてラミネートした感光性ドライフィルムを、露光量10mJ/cm2にて、パターンをレーザ露光し、その後現像をおこない、残った密着/解像(ライン&スペース)パターンの最小寸法を評価した。解像性評価(ライン&スペース)は、オルボテック社テストパターンを用いて行なった。
感光性ドライフィルムを5mJ/cm2にて露光後、めっき液に浸漬(室温)して疲労めっき液を作製した。その後、ハルセル試験を行い、めっき後の状態を蛍光X線装置を用いてすず比率、半田めっき厚を評価した。ハルセル試験とは、ハルセルに半田すずめっき液を入れ、電流1A、攪拌速度400rpmで10分間めっきを行い、めっき液の主成分の過不足、不純物の混入状況を評価する試験である。
上記表1に示す組成により化合物を攪拌混合して感光性樹脂組成物を調整し、実施例1と同様の方法にてドライフィルムを作成した。次いで、実施例1と同様の方法にてドライフィルムの各評価を行なった。
Claims (7)
- アルカリ可溶性樹脂(A)と、光重合性化合物(B)と、光重合開始剤(C)とを少なくとも有してなる感光性樹脂組成物において、
前記光重合性化合物(B)は、多価アルコールにα,β−不飽和カルボン酸を反応させて得られ、かつ、ビスフェノール骨格を有さない化合物(B−1)と、ビスフェノール骨格を有する化合物(B−2)とを含み、
前記光重合開始剤(C)は、少なくとも必須成分としてヘキサアリールビスイミダゾール系化合物(C1)と多官能チオール化合物(C2)とを含み、
前記化合物(B−1)がポリアルキレングリコールジ(メタ)アクリレートであることを特徴とする感光性樹脂組成物。 - 前記光重合開始剤(C)の必須成分(C1)100質量部に対する必須成分(C2)の配合量は、0.1〜30質量部であることを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記化合物(B−1)及び化合物(B−2)の配合量は、前記アルカリ可溶性樹脂(A)の固形分100質量部に対してそれぞれ10〜100質量部であることを特徴とする請求項1または2に記載の感光性樹脂組成物。
- 前記光重合開始剤(C)として、さらに、n−フェニルグリシンを含有することを特徴とする請求項1〜3のいずれか1項に記載の感光性樹脂組成物。
- レーザ走査露光用であることを特徴とする請求項1〜4のいずれか1項に記載の感光性樹脂組成物。
- 少なくとも支持フィルム上に請求項1〜4のいずれか1項に記載の感光性樹脂組成物から形成された感光性樹脂層を有することを特徴とする感光性ドライフィルム。
- レーザ走査露光用であることを特徴とする請求項6に記載の感光性ドライフィルム。
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JP2004340886A JP4315892B2 (ja) | 2004-11-25 | 2004-11-25 | 感光性樹脂組成物、およびこれを用いた感光性ドライフィルム |
CN200580039942XA CN101124517B (zh) | 2004-11-25 | 2005-11-22 | 感光性树脂组合物和使用它的感光性干膜 |
EP05811384A EP1825328B1 (en) | 2004-11-25 | 2005-11-22 | Photosensitive resin composition and photosensitive dry film by the use thereof |
DE602005014007T DE602005014007D1 (de) | 2004-11-25 | 2005-11-22 | Lichtempfindliche harzzusammensetzung und lichtempfindlicher trockener film durch verwendung davon |
US11/667,888 US7662541B2 (en) | 2004-11-25 | 2005-11-22 | Photosensitive resin composition and photosensitive dry film by the use thereof |
PCT/JP2005/021939 WO2006057423A2 (en) | 2004-11-25 | 2005-11-22 | Photosensitive resin composition and photosensitive dry film by the use thereof |
KR1020077011747A KR20070070238A (ko) | 2004-11-25 | 2005-11-22 | 감광성 수지 조성물 및 이를 이용한 감광성 드라이 필름 |
AT05811384T ATE428957T1 (de) | 2004-11-25 | 2005-11-22 | Lichtempfindliche harzzusammensetzung und lichtempfindlicher trockener film durch verwendung davon |
TW094141159A TWI307344B (en) | 2004-11-25 | 2005-11-23 | Photosensitive resin composition and photosensitive dry film by the use thereof |
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KR20150107644A (ko) * | 2014-03-14 | 2015-09-23 | 히타치가세이가부시끼가이샤 | 감광성 수지 조성물, 감광성 엘리먼트, 레지스트 패턴의 형성 방법 및 터치 패널의 제조 방법 |
KR102383138B1 (ko) * | 2014-03-14 | 2022-04-04 | 쇼와덴코머티리얼즈가부시끼가이샤 | 감광성 수지 조성물, 감광성 엘리먼트, 레지스트 패턴의 형성 방법 및 터치 패널의 제조 방법 |
KR20220044470A (ko) * | 2014-03-14 | 2022-04-08 | 쇼와덴코머티리얼즈가부시끼가이샤 | 감광성 수지 조성물, 감광성 엘리먼트, 레지스트 패턴의 형성 방법 및 터치 패널의 제조 방법 |
KR102526280B1 (ko) * | 2014-03-14 | 2023-04-28 | 가부시끼가이샤 레조낙 | 감광성 수지 조성물, 감광성 엘리먼트, 레지스트 패턴의 형성 방법 및 터치 패널의 제조 방법 |
Also Published As
Publication number | Publication date |
---|---|
EP1825328B1 (en) | 2009-04-15 |
EP1825328A2 (en) | 2007-08-29 |
CN101124517B (zh) | 2011-04-13 |
KR20070070238A (ko) | 2007-07-03 |
DE602005014007D1 (de) | 2009-05-28 |
ATE428957T1 (de) | 2009-05-15 |
TW200628496A (en) | 2006-08-16 |
TWI307344B (en) | 2009-03-11 |
CN101124517A (zh) | 2008-02-13 |
WO2006057423A3 (en) | 2007-09-27 |
US20070292804A1 (en) | 2007-12-20 |
WO2006057423A2 (en) | 2006-06-01 |
JP2006153984A (ja) | 2006-06-15 |
US7662541B2 (en) | 2010-02-16 |
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