CN103282829B - Photosensitive polymer combination - Google Patents
Photosensitive polymer combination Download PDFInfo
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- CN103282829B CN103282829B CN201180062574.6A CN201180062574A CN103282829B CN 103282829 B CN103282829 B CN 103282829B CN 201180062574 A CN201180062574 A CN 201180062574A CN 103282829 B CN103282829 B CN 103282829B
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- mass
- polymer combination
- photosensitive polymer
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- compound
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- 229920000642 polymer Polymers 0.000 title claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
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- 229920002521 macromolecule Polymers 0.000 claims abstract description 13
- 239000000539 dimer Substances 0.000 claims abstract description 6
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims abstract 2
- 229920005989 resin Polymers 0.000 claims description 62
- 239000011347 resin Substances 0.000 claims description 62
- 239000000758 substrate Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 47
- -1 (methyl) benzyl Chemical group 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 21
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 11
- 238000007747 plating Methods 0.000 claims description 11
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- 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 9
- 230000003252 repetitive effect Effects 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 3
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- 238000011156 evaluation Methods 0.000 description 19
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
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- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
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- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 8
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- 239000010949 copper Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
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- 230000008859 change Effects 0.000 description 4
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- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 4
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- 239000003112 inhibitor Substances 0.000 description 4
- 229960004194 lidocaine Drugs 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
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- 239000004065 semiconductor Substances 0.000 description 4
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- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- KFJDQPJLANOOOB-UHFFFAOYSA-N 2h-benzotriazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NNN=C12 KFJDQPJLANOOOB-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 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 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
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- 239000011889 copper foil Substances 0.000 description 3
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 3
- 230000008595 infiltration Effects 0.000 description 3
- 238000001764 infiltration Methods 0.000 description 3
- 238000003754 machining Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical class O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 2
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
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- 230000003628 erosive effect Effects 0.000 description 2
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
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- 230000007246 mechanism Effects 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
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- 150000000191 1,4-naphthoquinones Chemical class 0.000 description 1
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
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- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
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- KIJPZYXCIHZVGP-UHFFFAOYSA-N 2,3-dimethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C)C(C)=C2 KIJPZYXCIHZVGP-UHFFFAOYSA-N 0.000 description 1
- LZWVPGJPVCYAOC-UHFFFAOYSA-N 2,3-diphenylanthracene-9,10-dione Chemical compound C=1C=CC=CC=1C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1C1=CC=CC=C1 LZWVPGJPVCYAOC-UHFFFAOYSA-N 0.000 description 1
- JVCBVNUOEFLXGK-UHFFFAOYSA-N 2-(2-methoxyphenyl)-1h-imidazole Chemical class COC1=CC=CC=C1C1=NC=CN1 JVCBVNUOEFLXGK-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- SNFCQJAJPFWBDJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,5-diphenyl-1h-imidazole Chemical class C1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 SNFCQJAJPFWBDJ-UHFFFAOYSA-N 0.000 description 1
- CRBAESRLGGRIKR-UHFFFAOYSA-N 2-(hydroxymethyl)-2-pentan-2-ylpropane-1,3-diol Chemical compound CCCC(C)C(CO)(CO)CO CRBAESRLGGRIKR-UHFFFAOYSA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- GILMNGUTRWPWSY-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(O)COC(=O)C=C GILMNGUTRWPWSY-UHFFFAOYSA-N 0.000 description 1
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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
-
- 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
-
- 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
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- 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
- G03F7/027—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
-
- 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
-
- 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
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
- H05K3/061—Etching masks
- H05K3/064—Photoresists
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Graft Or Block Polymers (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
Abstract
The present invention relates to a kind of photosensitive polymer combination, it is the photosensitive polymer combination of the compound with (C) containing (A) alkali solubility macromolecule, (B) Photoepolymerizationinitiater initiater with ethylenical unsaturated double bonds, should (B) Photoepolymerizationinitiater initiater be 2,4,5 triarylimidazoles dimer or acridine compounds, and the compound that (C) has ethylenical unsaturated double bonds comprises the compound shown in following logical formula (I), in formula, R1、R2、A、B、n1、n2And n3It is defined as in the description.The developer solution dispersion stabilization of described photosensitive polymer combination is excellent, can suppress the generation of aggregation, has the developability of appropriateness, the flexibility of solidification resist layer and good elching resistant.
Description
Technical field
The present invention relates to photosensitive polymer combination etc..
Background technology
The Precision Machining etc. of printed circuit board (PCB) or metal was manufactured by photoetching process in the past.Photoetching process is this
Sample one method, i.e. be coated on substrate by photosensitive polymer combination, by pattern exposure, makes
The exposed portion polymerizing curable of this photosensitive polymer combination, removes unexposed portion with developer solution,
Form corrosion-resisting pattern on substrate, implement etching or plating, form conductive pattern, then, from this
Peel off on substrate and remove this corrosion-resisting pattern, thus the method forming conductive pattern on substrate.
In photolithography, when being coated on substrate by photosensitive polymer combination, following can be used
One method: photoresist solution is coated on substrate and is allowed to dry method, or by supporter,
The layer (hereinafter referred to as photo-sensitive resin) formed by photosensitive polymer combination and guarantor as required
The photosensitive-resin layered product that sheath is sequentially laminated and obtains is laminated to the method on substrate, at printing electricity
The manufacture of road plate is used mostly the latter.
The method that the above-mentioned photosensitive-resin layered product of use briefly described below manufactures printed circuit board (PCB).
First, from photosensitive-resin layered product, the protective layers such as polyethylene film are peeled off.Then, use
Laminating machine, on the substrates such as copper clad laminate, according to this substrate, photo-sensitive resin, supporter
Sequentially, photo-sensitive resin and supporter are laminated.Then, across having the photomask of wiring pattern,
This photo-sensitive resin is exposed, so that exposed portion polymerizing curable.Then, will be by poly-to benzene two
The supporter that formic acid glycol ester etc. are formed is peeled off.Then, aobvious by having the weakly alkaline aqueous solution etc.
Shadow liquid, dissolves the unexposed portion of photo-sensitive resin or dispersion is removed, and is formed against corrosion on substrate
Pattern.The operation quilt of the photo-sensitive resin of unexposed portion is removed by this developing solution dissolution or dispersion
It is referred to as developing procedure, the shortest time quilt needed for making the photo-sensitive resin of unexposed portion dissolve
It is referred to as minimum developing time.
Photosensitive polymer combination not all dissolving in developer solution, be often repeated once developing procedure,
The insoluble composition of developer solution bad dispersibility increases, and produces aggregation.Aggregation is attached on substrate,
Become the reason of short trouble.
Then, the corrosion-resisting pattern formed, as protection mask, carries out known etch processes or pattern
Plating.Finally, from substrate, peel off this corrosion-resisting pattern, manufacture have conductive pattern substrate,
I.e. printed circuit board (PCB).
In an etching process, the elching resistant of corrosion-resisting pattern is important.If elching resistant is poor, erosion
During quarter, etching solution is penetrated into from the gap between corrosion-resisting pattern and substrate, and the part at circuit top is eclipsed
Carve.Appearance in terms of top-direction has seen the variable color because infiltration causes, oxidation, segment conductor
The repeatability of the width of pattern is deteriorated, and linearity is poor and unstable.Additionally, during elching resistant difference, send out
The breach of raw conductive pattern or broken string.Conductive pattern is the finest, and these defects are the most notable.With above-mentioned shape
The operation that the etched pattern become carries out known etch processes as protection mask is referred to as etching work procedure.
Mostly above-mentioned developing procedure is linked with etching work procedure, need not leading of part owing to needing to be completely dissolved
Body, therefore the transporting velocity of substrate depends on etching work procedure.Now, in the minimum of photo-sensitive resin
In the case of developing time is short, exists and be exceedingly exposed to developer solution, infringement base material and resisting of being formed
The situation of the adaptation of corrosion figure case, this is especially using to improve image resolution ratio and etching efficiency
Become notable in the case of the photo-sensitive resin that thickness is thin.It addition, at developing procedure and etching work procedure
In, time solidification resist layer lacks flexibility, with contacting or developer solution or etching solution of conveying roller
Spraying will cause part corrosion-resisting pattern defect, and breach or the broken string of conductive pattern occur sometimes.
Under the above conditions, in order to improve flexibility and the chemical-resistant of solidification resist layer, report has
The method using polytetramethylene glycol two (methyl) acrylate or the method using carbamate compounds
(with reference to patent document 1,2).
Prior art literature
Patent document
Patent document 1: Japanese Laid-Open Patent Publication 61-228007 publication
Patent document 2: No. 3859934 publications of Japanese Patent No.
Summary of the invention
The problem that invention is to be solved
Chemical-resistant described in patent document 1 and 2 with aqueous alkali or plating liquid as object,
The patience of the not open acidic chemical to using in etching work procedure, does not the most disclose developability or poly-
Collection property.Therefore, however it remains provide that developer solution dispersion stabilization is excellent, can suppress aggregation generation,
There is the developability of appropriateness, the flexibility of solidification resist layer and the photoresist group of good elching resistant
The necessity of compound.
In view of above-mentioned present situation, problem to be solved by this invention be to provide developer solution dispersion stabilization excellent,
The generation that can suppress aggregation, the developability with appropriateness, the solidification flexibility of resist layer and the most resistance to
The photosensitive polymer combination etc. of etching.
For solving the scheme of problem
The present inventor in order to solve the problems referred to above further investigation, repeatedly test, it was found that by with
Lower technological means can solve the problems referred to above, this completes the present invention.
That is, the present invention is as described below.
[1] a kind of photosensitive polymer combination, it is to gather containing (A) alkali solubility macromolecule, (B) light
Close the photosensitive polymer combination that initiator has the compound of ethylenical unsaturated double bonds with (C), be somebody's turn to do (B)
Photoepolymerizationinitiater initiater is 2,4,5-triarylimidazoles dimer or acridine compounds, and should (C) have
The compound of ethylenical unsaturated double bonds comprises the compound shown in following logical formula (I):
In formula (I), R1And R2Representing hydrogen atom or methyl independently of one another, A is C2H4Or C3H6,
At-(A-O)n1-and-(A-O)n3In-,-C2H4-O-and-C3H6The arrangement of the repetitive of-O-is optionally nothing
That advise or block, in the case of this is arranged as block ,-C2H4-O-and-C3H6Any one of-O-exists
-B-O-group side, B is the divalent alkyl chain of carbon number 4～8, n1It is the integer of 0～10, n3It is 0～10
Integer, n1+n3It is the integer of 0～10, and n2It it is the integer of 1～20.
[2] according to the photosensitive polymer combination described in [1st] item, wherein, described (C) have olefinic
The compound of unsaturated double-bond also comprises the compound shown in following logical formula (II):
In formula (II), R3And R4It is hydrogen atom or methyl independently of one another, n4And n7It is independently of one another
The integer of 0～20, n4+n7It is the integer of 0～40, n5And n6It is the integer of 1～20 independently of one another, n5+n6
It is the integer of 2～40, and-(C2H4-O)-and-(C3H6-O)-the arrangement of repetitive be optionally random
Or block, in the case of this is arranged as block ,-(C2H4-O)-and-(C3H6-O)-any one
Bisphenol group side.
[3] according to the photosensitive polymer combination described in [2nd] item, wherein, in described logical formula (II),
n4And n7It is the integer of 1～20 independently of one another, and n4+n7It it is the integer of 2～40.
[4] according to [1st]～[3] item any one described in photosensitive polymer combination, wherein, described
(A) alkali solubility macromolecule selected from containing styrene and/or (methyl) benzyl acrylate as copolymer
The alkali solubility macromolecule of composition.
[5] according to [1st]～[4] item any one described in photosensitive polymer combination, wherein, described
In logical formula (I), n2It is the integer of 1～10, and n1+n3It is 0.
[6] according to [1st]～[5] item any one described in photosensitive polymer combination, wherein, described (C)
There is the compound of ethylenical unsaturated double bonds also comprise intramolecular there is at least one amino-formate bond
Compound.
[7] according to [1st]～[6] item any one described in photosensitive polymer combination, wherein, described (C)
There is the compound of ethylenical unsaturated double bonds and also comprise the compound shown in following logical formula (III):
In formula (III), R5And R6It is hydrogen atom or methyl independently of one another, n8And n9It is independently of one another
The integer of 3～40, and-(C2H4-O)-and-(C3H6-O)-the arrangement of repetitive be optionally random
Or block.
[8] according to [1st]～[7] item any one described in photosensitive polymer combination, wherein, described (C)
The compound with ethylenical unsaturated double bonds also comprises the change shown in following logical formula (IV) and/or (V)
Compound:
In formula (IV), R5And R6It is hydrogen atom or methyl independently of one another, n10～n12Independently of one another
It it is the integer of 1～30；
In formula (V), R5And R6It is hydrogen atom or methyl independently of one another, n10～n12It is independently of one another
The integer of 1～30.
[9] according to [1st]～[8] item any one described in photosensitive polymer combination, wherein, described (C)
There is the compound of ethylenical unsaturated double bonds also comprise intramolecular there is the compound of isocyanurate group.
[10] according to [1st]～[9] item any one described in photosensitive polymer combination, wherein, with sense
The solid point gross mass of photosensitive resin composition is 100 mass % meters, described (A) alkali solubility macromolecule
Use level be 40 mass %～80 mass %；With the solid point gross mass of photosensitive polymer combination for 100
Quality % is counted, and the use level of described (B) Photoepolymerizationinitiater initiater is 0.1 mass %～20 mass %；With sense
The solid point gross mass of photosensitive resin composition is 100 mass % meters, and described (C) has olefinic insatiable hunger
It is 5 mass %～50 mass % with the use level of the compound of double bond.
[11] a kind of photosensitive-resin layered product, it is to be pressed with by [1st]～[10] supporting film upper strata
The photo-sensitive resin of the photo-sensitive resin that the photosensitive polymer combination described in any one of item is formed
Laminate.
[12] manufacture method of a kind of substrate being formed with corrosion-resisting pattern, it is included in substrate overlaminate
[11] the lamination operation of the photosensitive-resin layered product described in item；Across mask by this layered photosensitive-resin
The exposure process of body exposure；And remove the developing procedure of unexposed portion.
[13] a kind of method forming circuit substrate, it is to by the method manufacture described in [12nd] item
Substrate be etched or plating and form circuit substrate.
The effect of invention
By the invention it is possible to provide that developer solution dispersion stabilization is excellent, can suppress aggregation generation,
There is the developability of appropriateness, flexibility and the good elching resistant of solidification resist layer, be applicable to be formed
The photosensitive polymer combination of good conductive pattern and there is the photonasty tree formed by said composition
The photosensitive-resin layered product etc. of lipid layer.
Detailed description of the invention
Hereinafter, the mode (hereinafter referred to as embodiment) for implementing the present invention is described in detail.Wherein,
The present invention is not limited to implementation below, can carry out various deformation and implement in the range of its main idea.
<photosensitive polymer combination>
In the present embodiment, photosensitive polymer combination contains (A) alkali solubility macromolecule, (B)
Photoepolymerizationinitiater initiater and (C) have the compound of ethylenical unsaturated double bonds.
<(A) alkali solubility macromolecule>
(A) alkali solubility macromolecule refers to the vinyl resin containing carboxyl, such as, is (methyl)
The copolymer of acrylic acid, (methyl) acrylate, (methyl) acrylonitrile, (methyl) acrylamide etc..
(A) alkali solubility macromolecule contains carboxyl, and acid equivalent is preferably 100～600.From improve resistance to developability,
From the viewpoint of improving image resolution ratio and adaptation, acid equivalent is preferably more than 100, from improving development
From the viewpoint of property and fissility, preferably less than 600.Acid equivalent is more preferably 250～450.
(A) the high molecular weight average molecular weight of alkali solubility is preferably more than 5,000 and less than 500,000.From
Edge-melting (edge fuse) when the proterties of development aggregation, formation photosensitive-resin layered product, chip
Property etc. unexposed film proterties from the viewpoint of, the high molecular weight average molecular weight of (A) alkali solubility be preferably
More than 5,000, from the viewpoint of improving developability, preferably 500, less than 000.Herein, edge-melting
When property is to coil into drum as photosensitive-resin layered product, photosensitive polymer combination layer is from reel
End face overflow phenomenon.The phenomenon that when chip is to be cut off by unexposed film with cutter, fragment splashes,
When fragment is attached to the upper surface etc. of photosensitive-resin layered product, in post-exposure process etc., transfer
On mask, constitute the reason of substandard products.(A) the high molecular weight average molecular weight of alkali solubility is more preferably 5,000
Above and 300, less than 000, more preferably 10, more than 000 and 200, less than 000.
(A) alkali solubility macromolecule such as can be by by each one or in following two class monomers
Plant the above incompatible acquisition of monomer copolymerization.
First monomer is carboxylic acid or the acid anhydrides in molecule with a polymerism unsaturated group.Such as,
Can list (methyl) acrylic acid, fumaric acid, cinnamic acid, crotonic acid, itaconic acid, maleic anhydride,
Acid half ester etc..Particularly preferably (methyl) acrylic acid.Wherein, (methyl) acrylic acid refers to propylene
Acid or methacrylic acid.
Second comonomer is non-acid and has the list of at least one polymerism unsaturated group in molecule
Body.Such as, (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) can be listed
N-propyl, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) third
Olefin(e) acid isobutyl ester, (methyl) tert-butyl acrylate, (methyl) acrylic acid 2-hydroxyl ethyl ester, (methyl) third
Olefin(e) acid 2-hydroxypropyl acrylate, (methyl) 2-EHA, (methyl) benzyl acrylate；Vinyl alcohol
Esters, such as, vinylacetate；(methyl) acrylonitrile；Styrene, styrene derivative etc..Especially
Its preferred (methyl) methyl acrylate, (methyl) n-butyl acrylate, styrene, styrene derived
Thing and (methyl) benzyl acrylate.
As the copolymer composition in (A) alkali solubility macromolecule, optimization styrene or styrene derivative,
Its combined polymerization ratio is preferably 20 mass %～60 mass %.From having sufficient aggregation and elching resistant
From the viewpoint of Deng, this combined polymerization ratio is preferably more than 20 mass %, from the developability with appropriateness
From the viewpoint of cured film flexibility, below preferably 60 mass %.This combined polymerization ratio is more preferably
It is 20 mass %～50 mass %, more preferably 20 mass %～30 mass %.Additionally, as copolymerization
Thing composition, preferably by styrene or styrene derivative, (methyl) methyl acrylate and (methyl) third
Olefin(e) acid copolymerization and the copolymer that obtains.It addition, in addition to the foregoing, divide to obtain the image of excellence
The combined polymerization ratio of resolution, styrene or styrene derivative is preferably 40 mass %～60 mass %, this
Outward, as copolymer composition, preferably by styrene or styrene derivative, (methyl) methyl acrylate
(methyl) acrylic acid copolymer and the copolymer that obtains.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The high molecular use level of (A) alkali solubility in compound is preferably 40 mass %～the scope of 80 mass %,
More preferably 50 mass %～70 mass %.From the viewpoint of edge-melting, this use level is preferably 40 matter
Amount more than %, from the viewpoint of developing time, below preferably 80 mass %.
<(B) Photoepolymerizationinitiater initiater>
Above-mentioned photosensitive polymer combination contains 2,4,5-triarylimidazoles dimer or acridine compounds is made
Required composition for (B) Photoepolymerizationinitiater initiater.As their object lesson, such as, can list
2-(Chloro-O-Phenyl)-4,5-diphenyl-imidazole dimer, 2-(Chloro-O-Phenyl)-4,5-two (methoxyphenyl) imidazoles
Dimer, 2-(adjacent fluorophenyl)-4,5-diphenyl-imidazole dimer, 2-(o-methoxyphenyl)-4,5-hexichol
The 2,4,5-triarylimidazoles such as base imidazoles dimer, 2-(p-methoxyphenyl)-4,5-diphenyl-imidazole dimer
Dimer, 9-phenylacridine, 1, the acridine derivatives etc. such as double (9,9-acridinyl) heptane of 7-.
Except 2, beyond 4,5-triarylimidazoles dimers or acridine compounds, as photosensitive resin composition
The Photoepolymerizationinitiater initiater that can contain further in thing, such as, can list benzophenone, N, N '-tetramethyl
Base-4,4 '-dimethylamino benzopheone (Michler's keton), N, N '-tetraethyl-4,4 '-diaminobenzophenone,
4-methoxyl group-4 '-dimethylamino benzopheone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-1-fourth
The aromatic ketones such as ketone, 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholinyl-1-acetone；2-EAQ,
Phenanthrenequione, 2-tert-butyl group anthraquinone, prestox anthraquinone, 1,2 benzae thracene quinone, 2,3-benzo anthraquinone, 2-phenyl
Anthraquinone, 2,3-diphenyl anthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinones, 9,10-phenanthrenequione, 2-
The quinones such as methyl-1,4-naphthaquinone, 2,3-dimethyl anthraquinone；Benzoin methylether, benzoin ethyl ether, benzoin
The benzoin ether compounds such as phenylate；The benzil derivatives such as benzil methyl ketal；N-phenylglycine
Derivative；Coumarin series compounds；4,4 '-bis-(lignocaine) benzophenone etc..These photopolymerization cause
Agent can be used alone, it is also possible to is used in combination of two or more.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The use level of (B) Photoepolymerizationinitiater initiater in compound is preferably 0.1 mass～20 mass %.Fill from obtaining
From the viewpoint of the speed divided, this use level is preferably more than 0.1 mass %, from making the abundant transmission of light
To resist layer bottom surface, obtain good high image resolution from the viewpoint of, preferably 20 mass % with
Under.The preferred scope of this use level is 0.5 mass %～10 mass %.
The compound of ethylenical unsaturated double bonds<(C) have>
(C) compound with ethylenical unsaturated double bonds refers to have unsaturated pair of olefinic as described in literal
The compound of key.There is as (C) compound of ethylenical unsaturated double bonds, such as, two can be listed
(methyl) esters of acrylic acid.Wherein, (methyl) acrylate refers to acrylate or methacrylic acid
Ester.
Photosensitive polymer combination contains the compound shown in following logical formula (I) and has alkene as (C)
Belong to the compound of unsaturated double-bond.
In formula (I), R1And R2Representing hydrogen atom or methyl independently of one another, A is C2H4Or C3H6,
At-(A-O)n1-and-(A-O)n3In-,-C2H4-O-and-C3H6The arrangement of the repetitive of-O-is optionally nothing
That advise or block, in the case of this is arranged as block ,-C2H4-O-and-C3H6Any one of-O-exists
-B-O-group side, B is the divalent alkyl chain of carbon number 4～8, n1It is the integer of 0～10, n3It is 0～10
Integer, n1+n3It is the integer of 0～10, and n2It it is the integer of 1～20.
Wherein, by two (methyl) acrylate shown in above-mentioned logical formula (I) and other technical scheme group
When being combined into photosensitive polymer combination, it is possible to provide developer solution dispersion stabilization is excellent, can suppress aggregation
Generation, there is the developability of appropriateness, the solidification flexibility of resist layer and the sense of good elching resistant
Photosensitive resin composition, although the detail of its mechanism is the most indefinite, but is speculated as following effect.
I.e. being speculated as, logical two (methyl) acrylate shown in formula (I) has the group shown in-B-O-,
Compared with normally used oxy ethylene or oxypropylene, strand is longer and does not has side chain, because of
The free degree of this main chain is high, the flexibility of chemical constitution (being sometimes referred to as protuberance property (tenting)) is excellent.
Ftracture it addition, ehter bond typically has because acid causes the carbon adjacent with oxygen to stand nucleophilic substitution
Tendency, logical two (methyl) acrylate shown in formula (I) had-group of (B-O)-shown
In, the ratio at the cleacvage reaction position that acid produces is less than oxy ethylene or oxypropylene, it is believed that resistance to
Acid (being sometimes referred to as elching resistant) is excellent.
Additionally it is believed that logical two (methyl) acrylate shown in formula (I) had-(B-O)-shown
Group there is high lipophile, easily form the dispersion stabilization containing phenyl initiator of development aggregation
Excellent (generation of aggregation can be suppressed).
Wherein, about the developability of appropriateness, thus it is speculated that be derived from two (methyl) propylene shown in logical formula (I)
The lipophile of the appropriateness that acid esters is had.
In the compound shown in above-mentioned logical formula (I), n1And n3The integer of preferably 0.That is, n1+n3
The integer of preferably 0.More specifically, consider from the viewpoint such as edge-melting, ease of manufacturing, above-mentioned logical
The polytetramethylene glycol two (methyl) shown in the most following logical formula (VI) of compound preference shown in formula (I)
Acrylate.
In formula (VI), R1And R2Represent hydrogen atom or methyl, and n independently of one another2Preferably 1～20
Integer, the integer of more preferably 1～15, the integer of particularly preferably 1～10.
More specifically, such as, butanediol two (methyl) acrylate, dibutylene glycol can be listed
Two (methyl) acrylate, three butanediol two (methyl) acrylate, four butanediols two (methyl)
Acrylate, five butanediol two (methyl) acrylate, six butanediol two (methyl) acrylate,
Seven butanediol two (methyl) acrylate, eight butanediol two (methyl) acrylate, nine butanediols
Two (methyl) acrylate, ten butanediol two (methyl) acrylate, 11 butanediol two (first
Base) acrylate, ten dibutylene glycol two (methyl) acrylate, thirteen kinds of furuncles glycol two (methyl)
Acrylate, 14 butanediol two (methyl) acrylate, 15 butanediol two (methyl) propylene
Acid esters etc..
In the compound shown in above-mentioned logical formula (I) and (VI), n2The integer of preferably 1～20, more
The integer of preferably 1～15, the integer of particularly preferably 1～10.From the viewpoint of cured film flexibility,
n2It is preferably more than 1, on the other hand, from the viewpoint of elching resistant, n2It is preferably less than 20.More
Preferably, n2It it is the integer of 5～10.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
Above-mentioned logical formula (I) or the use level of the compound shown in (VI) in compound are preferably 1 mass %～15
Quality %.From the viewpoint of obtaining cured film flexibility, this use level is preferably more than 1 mass %,
From the viewpoint of elching resistant, below preferably 15 mass %.The preferred scope of this use level
Being 1 mass %～10 mass %, further preferred range is 3 mass %～10 mass %.
It addition, from the viewpoint of improving flexibility further, it is preferred that photosensitive resin composition
Thing has the change of ethylenical unsaturated double bonds possibly together with the compound shown in following logical formula (II) as (C)
Compound.
In formula (II), R3And R4It is hydrogen atom or methyl independently of one another, n4And n7It is independently of one another
The integer of 0～20, n4+n7It is the integer of 0～40, n5And n6It is the integer of 1～20 independently of one another, n5+n6
It is the integer of 2～40, and-(C2H4-O)-and-(C3H6-O)-the arrangement of repetitive be optionally random
Or block, in the case of this is arranged as block ,-(C2H4-O)-and-(C3H6-O)-any one
Bisphenol group side.
Wherein, by shown in the compound shown in above-mentioned logical formula (I) or (VI) and above-mentioned logical formula (II)
Compound when being applied in combination, it is achieved the photosensitive polymer combination that flexibility improves further, although
The detail of its mechanism is the most indefinite, but is speculated as the effect of the following stated.
That is, by shown in the compound shown in above-mentioned logical formula (I) or (VI) and above-mentioned logical formula (II)
When compound is applied in combination, thus it is speculated that improve the reactivity of photopolymerization.And, thus speculate, exposure
After cured film become more tough, be demonstrated by good toughness.
In above-mentioned logical formula (II), n4And n7It is the integer of 0～20 independently of one another, n4+n7Be 0～40 whole
Number, n5And n6It is the integer of 1～20 independently of one another, n5+n6It it is the integer of 2～40.It addition, n4+n5+n6+n7
Lower limit be preferably more than 2, on the other hand, its upper limit is preferably less than 40.From the flexibility of cured film
From the viewpoint of, n4+n5+n6+n7It is preferably more than 2, on the other hand, examines from the viewpoint of image resolution ratio
Consider, preferably less than 40.It addition, from the viewpoint of elching resistant, n4+n5+n6+n7More preferably
The lower limit of scope be more than 4, the upper limit be less than 20, the lower limit of further preferred range is more than 6,
The upper limit is less than 12.It addition, from the viewpoint of protuberance property, n4+n5+n6+n7Preferred scope
Lower limit be more than 16, the upper limit be less than 40, the lower limit of further preferred range is more than 30, on
It is limited to less than 40.Additionally, n4And n7It is the integer of 1～10 the most independently of one another, n4+n7More preferably
The integer of 1～20, on the other hand, n5+n6The integer of more preferably 2～20.
As the object lesson of the compound shown in above-mentioned logical formula (II), can list at the two of bisphenol-A
Hold the dimethylacrylate of the ethylene glycol of the oxirane of average 2 moles of addition respectively or at bisphenol-A
Average 5 moles of two ends respectively addition oxirane ethylene glycol dimethylacrylate, double
The oxirane of average 6 moles of addition and the Asia of the expoxy propane of average 2 moles are distinguished in the two ends of phenol A
The dimethylacrylate of alkyl diol, at the two ends addition addition ring of average 15 moles of bisphenol-A
The alkylidene of the dimethylacrylate of the aklylene glycol of the expoxy propane of oxidative ethane and average 2 moles
The dimethylacrylate etc. of glycol.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The use level of the compound shown in above-mentioned logical formula (II) in compound is preferably 5 mass %～20 mass %.
From the viewpoint of obtaining elching resistant, this use level is preferably more than 5 mass %, soft from cured film
From the viewpoint of property, below preferably 20 mass %.The preferred scope of this use level is 5 matter
Amount %～15 mass %, further preferred range is 7 mass %～15 mass %.
From the viewpoint of improving cured film flexibility, photosensitive polymer combination is preferably possibly together with following
Logical compound shown in formula (III) has the compound of ethylenical unsaturated double bonds as (C).
In formula (III), R5And R6It is hydrogen atom or methyl independently of one another, n8And n9It is independently of one another
The integer of 3～40, and-(C2H4-O)-and-(C3H6-O)-the arrangement of repetitive be optionally random
Or block.
In the compound shown in above-mentioned logical formula (III), from the viewpoint of improving cured film flexibility,
n8And n9It is the integer of more than 3 the most independently of one another, the integer of more preferably more than 5.
As the object lesson of the compound shown in above-mentioned logical formula (III), such as, can list and add
Become average 9 moles expoxy propane polypropylene glycol on further average 1 moles of ethylene oxide of addition
The dimethylacrylate etc. of PAG.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The use level of the compound shown in above-mentioned logical formula (III) in compound is preferably 1 mass %～20 mass %.
From the viewpoint of obtaining cured film flexibility, this use level is preferably more than 1 mass %, from etch resistant
From the viewpoint of property, below preferably 20 mass %.The preferred scope of this use level is 3 matter
Amount %～15 mass %, further preferred range is 5 mass %～10 mass %.
From the viewpoint of improving cured film flexibility, photosensitive polymer combination is preferably possibly together with following
Compound shown in logical formula (IV) and/or (V) has the chemical combination of ethylenical unsaturated double bonds as (C)
Thing.
In formula, R5And R6It is hydrogen atom or methyl independently of one another, n10～n12It is 1～30 independently of one another
Integer；
In formula, R5And R6It is hydrogen atom or methyl independently of one another, n10～n12It is 1～30 independently of one another
Integer.
In the compound shown in above-mentioned logical formula (IV) or (V), from improving cured film flexibility
Viewpoint considers, n10～n12Preferably it is each independently the integer of more than 1, the integer of more preferably more than 3.
As the object lesson of the compound shown in above-mentioned logical formula (IV) or (V), such as, can arrange
The addition respectively at two ends further on the polypropylene glycol of the expoxy propane having enumerated in addition average 18 moles
The dimethylacrylate of the PAG of each average 7 moles of ethylene oxide, in addition average 18
Mole expoxy propane polypropylene glycol on respectively each average 3 moles of epoxy second of addition at two ends further
The dimethylacrylate of the PAG of alkane, in addition the expoxy propane of average 12 moles
Further at the PAG of two ends difference each average 3 moles of ethylene oxide of addition on polypropylene glycol
Dimethylacrylate, exist further on the polyethylene glycol of the oxirane of average 6 moles in addition
The dimethylacrylate etc. of the two ends PAG of each average 6 mol propylenoxy of addition respectively.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
Above-mentioned logical formula (IV) or the use level of the compound shown in (V) in compound are preferably 1 mass %～30
Quality %.From the viewpoint of obtaining elching resistant, this use level is preferably more than 1 mass %, from solid
From the viewpoint of changing film flexibility, below preferably 30 mass %.The preferred scope of this use level
Being 5 mass %～25 mass %, further preferred range is 5 mass %～23 mass %.
Photosensitive polymer combination preferably has the change of at least one amino-formate bond possibly together with intramolecular
Compound has the compound of ethylenical unsaturated double bonds as (C).Specifically, six methylenes can be listed
Group diisocyanate, toluene di-isocyanate(TDI), 2,2,4-trimethyl hexamethylene diisocyanates etc. two are different
Cyanate esters and (methyl) acrylic acid 2-hydroxypropyl acrylate, (methyl) acrylic acid oligoethylene glycol ester,
Hydroxyl (methyl) acrylate compounds such as (methyl) oligomeric propylene glycol ester of acrylic acid react and obtain
Carbamate compounds.From the viewpoint of elching resistant, it is preferred that intramolecular have to
Few the compound e.g. hexamethylene diisocyanate of an amino-formate bond, toluene diisocynate
The diisocyanate cpds such as ester, 2,2,4-trimethyl hexamethylene diisocyanate and (methyl) propylene
The carbamate compounds that acid oligomeric propylene glycol ester reaction obtains.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
Above-mentioned intramolecular in compound has the use level of the compound of at least one amino-formate bond and is preferably
5 mass %～20 mass %.From the viewpoint of obtaining elching resistant, this use level is preferably 5 mass %
Above, from the viewpoint of aggregation, below preferably 20 mass %.This use level preferred
Scope is 8 mass %～20 mass %, and further preferred range is 8 mass %～17 mass %.
Photosensitive polymer combination preferably has the compound conduct of isocyanurate group possibly together with intramolecular
(C) there is the compound of ethylenical unsaturated double bonds.Specifically, as intramolecular, there is isocyanuric acid
The compound of ester group, such as, can list ethoxylation isocyanuric acid triacrylate, 6-caprolactone
Modified single (2-acryloyl-oxyethyl) isocyanuric acid ester, 6-caprolactone modified double (2-acryloyl-oxyethyl)
Isocyanuric acid ester, 6-caprolactone modification three (2-acryloyl-oxyethyl) isocyanuric acid ester, isocyanuric acid ring
The ethylene-oxide-modified diacrylate of oxidative ethane modification acrylate, isocyanuric acid, isocyanuric acid epoxy
Oxide-modified triacrylate, isocyanuric acid epoxy pronane modification acrylate, isocyanuric acid epoxy third
Alkane modified diacrylate, isocyanuric acid epoxy pronane modification triacrylate etc..
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The use level of the compound that the intramolecular in compound has isocyanurate group is preferably 1 mass %～20 matter
Amount %.From the viewpoint of obtaining elching resistant, this use level is preferably more than 1 mass %, from solidification
From the viewpoint of film flexibility, below preferably 20 mass %.This use level more preferably in the range of 1
Quality %～15 mass %, further preferred range is 2 mass %～10 mass %.
Have the compound of ethylenical unsaturated double bonds as (C), photosensitive polymer combination is except containing
Compound shown in choosing freely above-mentioned logical formula (I)～(VI), intramolecular have at least one amino first
The compound of acid esters key, intramolecular have isocyanuric acid base compound composition group in compound with
Outward, also can be containing the alefinically unsaturated compounds of following shown photopolymerization.
Specifically, as the alefinically unsaturated compounds of photopolymerization, polypropylene glycol two can be listed
(methyl) acrylate, polyethylene glycol (methyl) acrylate, 2-bis-(p-hydroxybenzene) propane (first
Base) acrylate, glycerine three (methyl) acrylate, trihydroxy methyl three (methyl) acrylate,
Polyoxyethyl propyl trimethylolpropane tris (methyl) acrylate, polyoxyethanyl trimethylolpropane tris (first
Base) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) third
Olefin(e) acid ester, trimethyl propane triglycidyl ether three (methyl) acrylate, phenoxy group polyethylene glycol
(methyl) acrylate, Nonylphenoxy polyethylene glycol (methyl) acrylate etc..These are permissible
It is used alone, it is also possible to be used in combination of two or more.
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The use level of the compound that (C) in compound has ethylenical unsaturated double bonds is preferably 5 mass %～50
Quality %.From the viewpoint of speed, image resolution ratio, adaptation, this use level is preferably 5 matter
Amount more than %, from the viewpoint of the stripping of suppression cold flow and solidification resist layer postpones, preferably 50 matter
Amount below %.This use level is more preferably 25 mass %～45 mass %.
<leuco dye, fluoran dyes, coloring material>
Photosensitive polymer combination can also contain leuco dye, fluoran dyes or coloring material.Pass through
Containing these dyestuffs, exposed portion develops the color, is therefore preferred from the viewpoint of visuality, it addition,
Inspection equipment etc. read when the alignment mark of exposure, exposed portion and the contrast of unexposed portion
If great, then easily identify but favourable.
As leuco dye, three (4-dimethylamino phenyl) methane [leuco crystal violet], double (4-can be listed
Dimethylamino phenyl) phenylmethane [leucogentian violet].Especially, from the viewpoint of contrast is good,
As leuco dye, leuco crystal violet is preferably used.
As fluoran dyes, 2-(dibenzyl amino) fluorane, 2-anilino--3-methyl-6-diethyl can be listed
Amino fluorane, 2-anilino--3-methyl-6-dibutylamino fluorane, 2-anilino--3-methyl-6-N-ethyl-N-
C fluorane, 2-anilino--3-methyl-6-N-methyl-N-cyclohexyl amino fluorane, 2-anilino-
-3-chloro-6-lignocaine fluorane, 2-anilino--3-methyl-6-N-ethyl-N-isobutylamino fluorane, 2-
Anilino--6-dibutylamino fluorane, 2-anilino--3-methyl-6-N-ethyl-N-tetrahydrofurfuryl amino fluorane,
2-anilino--3-methyl-6-piperidyl amino fluorane, 2-(o-chloraniline base)-6-lignocaine fluorane,
2-(3,4-dichloroanilino)-6-lignocaine fluorane etc..
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
Leuco dye or the content of fluoran dyes in compound are preferably 0.1 mass %～10 mass %.From exposure portion
Point with the contrast of unexposed portion from the viewpoint of, this content is preferably more than 0.1 mass %, from dimension
From the viewpoint of holding storage stability, below preferably 10 mass %.
As coloring material, such as, magenta, phthalocyanine green, alkali Chinese scholartree Huang, paramagenta (para can be listed
Magenta), crystal violet, methyl orange, Nile blue 2B, Victoria blue, malachite green (soil conservation paddy
Chemistry (strain) Aizen(processed registration mark), MALACHITE GREEN), alkali blue 20, alkali
Property green (hodogaya chemical (strain) Aizen(processed registration mark) DIAMOND GREEN GH).
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photosensitive polymer combination
In the content of coloring material be preferably 0.001 mass %～1 mass %.Examine from the viewpoint improving treatability
Considering, this content is preferably more than 0.001 mass %, and from the viewpoint of maintaining storage stability, this contains
Amount is preferably below 1 mass %.
<halogen compounds>
In embodiments of the present invention, from the viewpoint of adaptation and contrast, it is preferred that
Leuco dye is applied in combination by photosensitive polymer combination with following halogen compounds.
As halogen compounds, such as, can list amyl bromide, isoamyl bromide, brominated isobutylene,
Ethylene bromide, diphenylmethyl bromide, benzyl bromide a-bromotoluene, methylene bromide, trisbromomethyl phenyl sulfone, tetrabormated
Carbon, three (2,3-dibromopropyl) phosphate, trichloroacetamide, amyl iodide, isobutyl iodide, 1,1,1-tri-
Chloro-2,2-double (rubigan) ethane, chlorination triaizine compounds etc., particularly preferred trisbromomethyl phenyl
Sulfone.It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The content of the halogen compounds in compound is preferably 0.01 mass %～3 mass %, from obtaining adaptation and right
From the viewpoint of degree, this use level is preferably more than 0.01%, from the viewpoint of storage stability,
It is preferably below 3 mass %.
<radical polymerization inhibitor, benzotriazole, carboxyl benzotriazole class>
It addition, in order to improve the heat endurance of photosensitive polymer combination, storage stability, photonasty
Resin combination can contain the free radical polymerization inhibitor of choosing, benzotriazole and carboxyl further
At least one above compound in the group of benzotriazole composition.
As radical polymerization inhibitor, such as, p methoxy phenol, quinhydrones, adjacent benzene can be listed
Triphenol, naphthylamines, tert-butyl catechol, stannous chloride, 2,6-di-t-butyl-paracresol, 2,2 '-methylene
Base double (4-methyl-6-tert-butylphenol), 2,2 '-methylene-bis(4-ethyl-6-t-butyl phenol), nitroso
Phenylhydroxylamine aluminium salt, diphenyl nitroso-amines etc..
As benzotriazole, such as, 1,2,3-BTAs, chloro-1,2, the 3-benzos three of 1-can be listed
Azoles, double (N-2-ethylhexyl) aminomethylene-l, 2,3 triazole, double (N-2-ethylhexyl) amino
Methylene-1,2,3-tolytriazole, double (N-2-ethoxy) aminomethylene-l, 2,3 triazole etc..
As carboxyl benzotriazole class, such as, 4-carboxyl-1,2,3-BTAs, 5-carboxyl can be listed
-l, 2,3 triazole, N-(N, N-bis--2-ethylhexyl) aminomethylene carboxyl benzotriazole, N-(N, N-
Two-2-ethoxys) aminomethylene carboxyl benzotriazole, N-(N, N-bis--2-ethylhexyl) aminoethylene
Carboxyl benzotriazole etc..
The total content of radical polymerization inhibitor, BTA and carboxyl benzotriazole class is relative to whole
Individual photosensitive polymer combination is preferably 0.01 mass %～3 mass %, more preferably 0.05 mass %～1 matter
Amount %.From the viewpoint of imparting photosensitive polymer combination is with storage stability, this content is preferably
More than 0.01 mass %, from maintain speed, suppress dye decolored from the viewpoint of, preferably 3 mass %
Below.
<plasticizer>
Photosensitive polymer combination can also contain plasticizer as required.As this plasticizer, example
As, the Phthalates such as diethyl phthalate can be listed；Orthotoluene sulfonamide, to toluene
Sulfonamide, ATBC, triethyl citrate, CitroflexA-2, acetyl group lemon
Lemon acid three n-propyls, acetyl tributyl citrate, polyethylene glycol, polypropylene glycol, polyethylene glycol
Alkyl ether, polypropylene glycol alkyl ether etc..
It is 100 mass % timing with the solid point gross mass of photosensitive polymer combination, photoresist group
The content of the plasticizer in compound is preferably 1 mass %～50 mass %, more preferably 1～30 mass %.From
From the viewpoint of suppression developing time delay, imparting cured film are with flexibility, this content is preferably 1 matter
Amount more than %, from the viewpoint of suppression solidifies insufficient or cold flow, below preferably 50 mass %.
<solvent>
As the solvent for dissolving photosensitive polymer combination, can list with MEK (MEK)
For the ketone represented, the alcohols etc. with methyl alcohol, ethanol or isopropanol as representative.This solvent preferably adds
In photosensitive polymer combination so that for being applied to the photosensitive polymer combination on support film
The viscosity of solution be 500mPa s～4000mPa s at 25 DEG C.
<photosensitive-resin layered product>
In the present embodiment, photosensitive-resin layered product includes being formed by photosensitive polymer combination
Photo-sensitive resin and support film.It addition, photo-sensitive resin preferably layer is pressed on support film.
As required, the surface with support film side opposite side of photo-sensitive resin can have guarantor
Sheath.
As supporting film, it is generally desirable to, through the transparent support film of the light launched from exposure light source.
As this support film, such as, ethylene glycol terephthalate film, polyvinyl alcohol can be listed
Film, polyvinyl chloride film, vinyl chloride copolymer film, polyvinylidene chloride film, inclined two chloroethenes
Alkene copolymer film, polymethyl methacrylate copolymer film, polystyrene film, polyacrylonitrile
Film, styrol copolymer film, polyamide film, cellulose derivative film etc..These films
Stretched film, the preferably film of mist degree less than 5 can be used as required.The thickness of film is thin at figure
As the aspect of formative and economy is favourable, but in order to maintain intensity, 10 μm are preferably used
～30 films of μm.
The key property of the protective layer used in photosensitive-resin layered product is itself and photo-sensitive resin
Closing force is sufficiently smaller than the closing force supporting film with photo-sensitive resin, can be easily peeled off.Example
As, polyethylene film, polypropylene film etc. use preferably as protective layer.Furthermore it is also possible to use
The film that fissility shown in Japanese Laid-Open Patent Publication 59-202457 publication is excellent.The thickness of protective layer is excellent
Elect 10 μm～100 μm, more preferably 10 μm～50 μm as.Photonasty in photosensitive-resin layered product
The thickness of resin bed is different according to purposes, preferably 5 μm～100 μm, more preferably 7 μm～60 μm,
The thinnest image resolution ratio is the highest, and more thick film intensity is the highest.Additionally, in the erosion that need not high protuberance property
Carving in purposes, the thickness of the photo-sensitive resin in photosensitive-resin layered product is preferably 10 μm
～20 μm.From the viewpoint of elching resistant, the thickness of photo-sensitive resin is more than 10 μm, from figure
As, from the viewpoint of resolution ratio, this thickness is below 20 μm.
<preparation method of photosensitive-resin layered product>
It is sequentially laminated as by supporting film, photo-sensitive resin and protective layer as required and makes
The method of photosensitive-resin layered product, can use known method.Such as, photonasty tree will be used for
The photosensitive polymer combination of lipid layer and dissolve its solvent mixing, forms homogeneous solution, first,
Use bar coater or roll coater coating on film supporting, be then dried, such that it is able to supporting film
The photo-sensitive resin that overlaminate is formed by photosensitive polymer combination.Then, as required photosensitive
Property resin bed overlaminate protective layer, such that it is able to make photosensitive-resin layered product.
<there is the manufacture method of the substrate of corrosion-resisting pattern>
Following description uses the method that photosensitive-resin layered product manufactures the substrate being formed with corrosion-resisting pattern
An example.As required, by the substrate etch that will so manufacture or plating, can manufacture
Circuit substrate or printed circuit board (PCB).
Use photosensitive-resin layered product to manufacture be formed with the substrate of corrosion-resisting pattern and employ this base
The circuit substrate of plate or the method for printed circuit board (PCB) include following operation.Wherein, operation (4) and (4 ')
Either of which person can be used, or both of which can be utilized.
(1) lamination operation
The protective layer of photosensitive-resin layered product is peeled off on limit, and limit uses hot roll laminator to make photoresist
The closely sealed operation on the substrate such as copper clad laminate, flexible base board of layered product.
(2) exposure process
Make the mask film with required wiring pattern closely sealed on supporter (such as supporting film etc.),
Utilize activity light source to be exposed, or implement the work of exposure by directly drawing required wiring pattern
Sequence.
(3) developing procedure
After exposure, the supporter on photo-sensitive resin is peeled off, is then used by the development of aqueous alkali
Liquid, development is removed unexposed portion, is formed the operation of corrosion-resisting pattern on substrate.
As aqueous alkali, it is, for example possible to use Na2CO3Or K2CO3The aqueous solution.Aqueous alkali
Characteristic according to photo-sensitive resin suitably selects, it is common that concentration be about 0.2 mass %～2 mass %,
About 20 DEG C～the Na of 40 DEG C2CO3The aqueous solution.
Through above-mentioned each operation, it is possible to obtain corrosion-resisting pattern, according to circumstances can also carry out about further
100 DEG C～the heating process of 300 DEG C.By implementing this heating process, chemicals-resistant can be improved further
Property.Heating can be to use hot blast, infrared ray, the heating furnace of far infrared mode.
(4) etching work procedure
Etching solution, the copper face that will do not covered by corrosion-resisting pattern is sprayed above the corrosion-resisting pattern formed
The operation of etching.
Etching work procedure uses acid etching, alkali etching etc. to be suitable for photosensitive-resin layered product used
Method carry out.
(4 ') plating process
Use copper facing, plating weldering (solder plating) etc., the substrate being formed with corrosion-resisting pattern is plated
The operation covered.
As the method for plating, can list and carry out electric plating method etc. using substrate as electrode.
(5) peel off
The aqueous solution using alkalescence to be better than developer solution afterwards peels off corrosion-resisting pattern from substrate.Use peeling off
Aqueous alkali be not particularly limited, generally use concentration about 2 mass %～5 mass %, temperature about 40 DEG C
～the aqueous solution of NaOH, KOH etc. of 70 DEG C.Stripper can also add a small amount of water-soluble solvent.
As it has been described above, present embodiment relates to the photosensitive resin composition that can be developed by alkaline aqueous solution
Thing, the photosensitive-resin layered product that this photosensitive polymer combination is formed at supporter overlaminate,
This photosensitive-resin layered product is used to form the method for corrosion-resisting pattern and this corrosion-resisting pattern on substrate
Purposes etc..These photosensitive polymer combinations etc. can provide the corrosion-resisting pattern being suitable for following manufacture:
The manufacture of printed circuit board (PCB), the manufacture of flexible printed circuit board, IC chip are installed with lead frame (following
Be referred to as lead frame) manufacture, metal forming Precision Machining, the BGA(BGA such as metal mask manufacture)
Or CSP(chip size packages) etc. semiconductor packages manufacture, with TAB(Tape Automated
Bonding, tape-automated bonding) or COF(Chip On Film: at the fine wiring plate of film-form
Upper installation semiconducter IC) it is the manufacture of tape winding substrate (tape substrate) of representative, semiconductor projection
Manufacture, ITO electrode in field of flat panel displays, addressing electrode, the parts such as electromagnetic wave shield
Manufacture.
Embodiment
By the following examples 1～14 and comparative example 1 and 2 specifically describe further.
First, the preparation method of the sample for evaluation of embodiment and comparative example is described, then shows institute
Obtain evaluation method and the evaluation result thereof of sample.
(1) preparation method of sample for evaluation
The sample for evaluation of embodiment and comparative example makes as follows.
<making of photosensitive layer laminate>
By the composition shown in table 1 below, (numeral of the most each composition represents the use level in terms of solid is divided
(mass parts)) photosensitive polymer combination and solvent be sufficiently stirred for, mix, formed photoresist
Composition blending liquid, uses bar coater to be coated on the poly-to benzene two of 16 μ m-thick as supporter equably
The surface of formic acid glycol ester film (Mitsubishi Polyester Film GmbH system, R130-16),
The drying machine of 95 DEG C is dried 1.5 minutes, forms photosensitive resin composition layer.Photosensitive resin composition
The thickness of layer is 15 μm.
Then, pet film it is not laminated at photosensitive resin composition layer
On surface, polyethylene film (TAMAPOLY CO., the LTD. of 19 μ m-thick fitted as protective layer
System, GF-818), it is thus achieved that photosensitive-resin layered product.Table 2 below shows in table 1 and use shorthand notation
The title of the material composition in the photosensitive polymer combination blending liquid represented.
<substrate leveling>
As developability, the evaluation substrate of elching resistant, use the 1.6mm being laminated 35 μm rolled copper foils
Thick copper clad laminate.Substrate surface is carried out wet type polishing roll grinding (3M company system, Scotch
Brite(registration mark) HD#600, by 2 times).
<lamination>
The polyethylene film of photosensitive-resin layered product is peeled off on limit, and limit uses hot roll laminator (Asahi Chemical Industry
(strain) makes, AL-700) it is pressed onto leveling in 105 DEG C of lower floors of roll temperature and is preheated to the copper clad layers pressure of 60 DEG C
On plate.Air pressure is set as, and 0.35MPa, laminate speed are set as 2.0m/ minute.
<exposure>
The necessary mask film of evaluating of photosensitive resin composition layer is placed on gathering as supporter
On ethylene glycol terephthalate film, at embodiment 1～6, embodiment 9～14 and comparative example 1 and 2
In, use ultrahigh pressure mercury lamp (ORC MANUFACTURING CO., LTD. system,
HMW-801) with 70mJ/cm2Light exposure be exposed.In embodiment 7 and 8, use and directly paint
Standard exposure device (Hitachi Via Mechanics, Ltd. system, DI exposure machine DE-1DH, light
Source: GaN royal purple diode, dominant wavelength 405 ± 5nm) with 15mJ/cm2Light exposure be exposed.
For the evaluation sample of cured film flexibility, at photosensitive-resin layered product fabricated as described above
The pet film as supporter on place that to evaluate necessary mask thin
Film, in embodiment 1～6, embodiment 9～14 and comparative example 1 and 2, uses ultrahigh pressure mercury lamp (ORC
MANUFACTURING CO., LTD. system, HMW-801) with 70mJ/cm2Light exposure
It is exposed.In embodiment 7 and 8, use and directly draw formula exposure device (Hitachi Via
Mechanics, Ltd. system, DI exposure machine DE-1DH, light source: GaN royal purple diode, dominant wavelength
405 ± 5nm) with 15mJ/cm2Light exposure be exposed.
<development>
About the evaluation substrate of developability and elching resistant, pet film is shelled
From afterwards, use alkali developing machine (FUJI KIKO., Co.Ltd. system, dry film developing machine), spraying
1 mass %Na of 30 DEG C of stipulated time2CO3The aqueous solution, dissolves and removes the unexposed of photo-sensitive resin
Part.Now, with the time development of 2 times of minimum developing time, solidification corrosion-resisting pattern is made.Wherein,
Minimum developing time refers to needed for the photo-sensitive resin for dissolving unexposed portion the most as mentioned above
Short time.
About the evaluation sample of cured film flexibility, after polyethylene film is peeled off, develop by minimum
Develop under 2 times of times, the same terms of time, it is thus achieved that solidification resist layer.
<etching>
On the evaluation substrate being defined corrosion-resisting pattern by development, use mantoquita Etaching device (Tokyo
Chemical industry machine (strain) is made, mantoquita Etaching device), spray stipulated time copper chloride concentration 250g/L, hydrochloric acid
50 DEG C of copper chloride etching solutions of concentration 3mol/L, dissolve remove on copper clad laminate not by resist pattern
The Copper Foil of the part that case covers.
<stripping>
On evaluation substrate after the etching, spraying is heated to the 3 mass % sodium hydrate aqueous solutions of 50 DEG C,
The resist layer of solidification is peeled off.
(2) evaluation method of sample
Then, the evaluation method of sample is described.
(i) developability
According to the preparation method of above-mentioned (1) sample for evaluation, make substrate, lamination, development, it is thus achieved that
Corrosion-resisting pattern.According to minimum developing time, classification as described below:
A: minimum developing time is more than 14 seconds.
B: minimum developing time be 10 seconds less than 14 seconds.
C: minimum developing time was less than 10 seconds.
(ii) elching resistant
According to the preparation method of above-mentioned (1) sample for evaluation, by exposed portion and unexposed portion
Width ratio is the line style pattern mask of 1:1, through the elching resistant evaluation substrate of 15 minutes after being laminated
Exposure.Further, by 2 times of time developments of minimum developing time, needed for Copper Foil being removed by etching
Time be set to minimum etching period, be etched with 1.4 times of times of minimum etching period.Use hydrogen-oxygen
Change sodium water solution and peel off solidification resist layer, use observation by light microscope conductive pattern, according to relevant sight
Examine result, proceed as described below classification:
A: conductive pattern is formed as linearity, does not see the infiltration of etching solution.
B: conductive pattern is formed as linearity, but sees the infiltration of etching solution.
C: conductive pattern is formed without as linearity, it is seen that concavo-convex.
(iii) flexibility of cured film
According to the preparation method of above-mentioned (1) sample for evaluation, rectangular by 5mm × 40mm
Mask is by made photosensitive-resin layered product exposure.Further, with 2 times of minimum developing time time
Between develop, it is thus achieved that solidification resist layer.With cupping machine (ORIENTEC Co., LTD. system,
RTM-500) with the speed of 100mm/ minute, the solidification resist layer of made 5mm × 40mm is drawn
Stretch, according to the elongation of solidification resist layer now, proceed as described below classification:
A+: the elongation of solidification resist layer is more than 45mm.
A: the elongation of solidification resist layer is that 40mm is less than 45mm.
B: the elongation of solidification resist layer is that 15mm is less than 40mm.
C: the elongation of solidification resist layer is less than 15mm.
(iv) aggregation
Make thickness 15 μm in photosensitive-resin layered product, area 2.0m2Photosensitive layer be dissolved in 200ml
1 mass %Na2CO3In the aqueous solution, use circulating sprayer unit, enter under atomisation pressure 0.1MPa
Row spraying 3 hours continuously.Hereafter, developer solution is stood 1 hour, it was observed that the generation of aggregation.Produce
During raw a large amount of aggregation, on the bottom surface and side of sprayer unit, it was observed that the aggregation of powdery or oil
The aggregation of shape.The combination that developer solution aggregation is good does not the most produce these aggregations.According to gathering
The generation state of thing, as described below carries out classification to aggregation:
A: the most do not produce aggregation.
B: see aggregation in the bottom of sprayer unit or a part for side.
C: see aggregation in whole sprayer unit.
The high molecular acid equivalent of (v) alkali solubility
Acid equivalent refers to the high molecular quality of alkali solubility wherein with the carboxyl of 1 equivalent.The survey of acid equivalent
Surely use flat natural pond industry (strain) to make flat natural pond automatic titration device (COM-555), use 0.1mol/L's
NaOH, carried out by potential difference titration.
(vi) weight average molecular weight
Weight average molecular weight use Japan's light splitting (strain) gel permeation chromatograph processed (GPC) (pump: Gulliver,
PU-1580 type；Post: Showa electrician (strain) Shodex(processed registration mark) (KF-807, KF-806M,
KF-806M, KF-802.5) 4 pieces series connection；Fluidized bed solvent: oxolane；Use polystyrene mark
The calibration curve that quasi-sample (Showa electrician (strain) Shodex processed STANDARD SM-105) obtains),
Obtain according to polystyrene conversion.
(3) evaluation result
Table 1 shows the evaluation result of embodiment and comparative example.
[table 1]
[table 2]
Industrial applicability
Above-mentioned photosensitive polymer combination and layered product can be suitable for printed circuit board (PCB), flexible printing
The metal forming Precision Machining such as circuit board, the manufacture of lead frame or metal mask manufacture, BGA or CSP etc.
Semiconductor packages manufactures, the manufacture of the tape winding substrates such as TAB or COF, the manufacture of semiconductor projection, ITO
Electrode or the manufacture of addressing electrode, electromagnetic wave shield etc..
Claims (13)
1. a photosensitive polymer combination, it is containing (A) alkali solubility macromolecule, (B) photopolymerization
Initiator and (C) have the photosensitive polymer combination of the compound of ethylenical unsaturated double bonds, are somebody's turn to do (B)
Photoepolymerizationinitiater initiater is 2,4,5-triarylimidazoles dimer or acridine compounds, and (C) should have alkene
The compound belonging to unsaturated double-bond comprises the compound shown in following logical formula (I):
In formula (I), R1And R2Representing hydrogen atom or methyl independently of one another, A is C2H4Or C3H6,
-(A-O)n1-and-(A-O)n3In-,-C2H4-O-and-C3H6The arrangement of the repetitive of-O-is optionally random
Or block, in the case of this is arranged as block ,-C2H4-O-and-C3H6Any one of-O-is at-B-O-base
Group side, B is the divalent alkyl chain of carbon number 4～8, n1It is the integer of 0～10, n3It is the integer of 0～10,
n1+n3It is the integer of 0～10, and n2It it is the integer of 5～20.
Photosensitive polymer combination the most according to claim 1, wherein, described (C) has alkene
The compound belonging to unsaturated double-bond also comprises the compound shown in following logical formula (II):
In formula (II), R3And R4It is hydrogen atom or methyl independently of one another, n4And n7It is 0～20 independently of one another
Integer, n4+n7It is the integer of 0～40, n5And n6It is the integer of 1～20 independently of one another, n5+n6It is 2～40
Integer, and-(C2H4-O)-and-(C3H6-O)-the arrangement of repetitive be optionally random or block
, in the case of this is arranged as block ,-(C2H4-O)-and-(C3H6-O)-any one in bisphenol group side.
Photosensitive polymer combination the most according to claim 2, wherein, in described logical formula (II)
In, n4And n7It is the integer of 1～20 independently of one another, and n4+n7It it is the integer of 2～40.
4. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, described (A)
Alkali solubility macromolecule selected from containing styrene and/or (methyl) benzyl acrylate as the alkali of copolymer composition
Soluble macromolecular.
5. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, described
In logical formula (I), n2It is the integer of 5～10, and n1+n3It is 0.
6. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, described (C)
There is the compound of ethylenical unsaturated double bonds be also included in intramolecular there is at least one amino-formate bond
Compound.
7. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, as institute
State (C) there is the compound of ethylenical unsaturated double bonds also to comprise the compound shown in following logical formula (III):
In formula (III), R5And R6It is hydrogen atom or methyl independently of one another, n8And n9It is independently of one another
The integer of 3～40, and-(C2H4-O)-and-(C3H6-O)-the arrangement of repetitive be optionally random or
Block.
8. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, described (C)
The compound with ethylenical unsaturated double bonds also comprises the chemical combination shown in following logical formula (IV) and/or (V)
Thing:
In formula (IV), R5And R6It is hydrogen atom or methyl independently of one another, n10～n12It is independently of one another
The integer of 1～30；
In formula (V), R5And R6It is hydrogen atom or methyl independently of one another, n10～n12It is independently of one another
The integer of 1～30.
9. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, described (C)
There is the compound of ethylenical unsaturated double bonds also comprise intramolecular there is the compound of isocyanurate group.
10. according to the photosensitive polymer combination described in any one of claims 1 to 3, wherein, with photosensitive
Property resin combination solid point gross mass be 100 mass % meter, described (A) alkali solubility is high molecular joins
Resultant is 40 mass %～80 mass %,
It is in terms of 100 mass % by the solid point gross mass of photosensitive polymer combination, described (B) photopolymerization
The use level of initiator is 0.1 mass %～20 mass %,
Being in terms of 100 mass % by the solid point gross mass of photosensitive polymer combination, described (C) has alkene
The use level of the compound belonging to unsaturated double-bond is 5 mass %～50 mass %.
11. 1 kinds of photosensitive-resin layered products, it is pressed with by claim 1～10 on support film upper strata
The photo-sensitive resin that photosensitive polymer combination described in any one is formed.
The manufacture method of 12. 1 kinds of substrates being formed with corrosion-resisting pattern, comprising: weigh at substrate overlaminate
Profit requires the lamination operation of the photosensitive-resin layered product described in 11；Across mask by this photo-sensitive resin
The exposure process of laminate exposure；And remove the developing procedure of unexposed portion.
13. 1 kinds of methods forming circuit substrate, it is to by the method manufacture described in claim 12
Substrate be etched or plating and form circuit substrate.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-288105 | 2010-12-24 | ||
| JP2010288105 | 2010-12-24 | ||
| PCT/JP2011/077415 WO2012086371A1 (en) | 2010-12-24 | 2011-11-28 | Photosensitive resin composition |
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| CN103282829B true CN103282829B (en) | 2016-08-17 |
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| JP (2) | JP5707420B2 (en) |
| KR (3) | KR102019580B1 (en) |
| CN (1) | CN103282829B (en) |
| MY (1) | MY179988A (en) |
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| JP6207943B2 (en) * | 2013-09-19 | 2017-10-04 | 旭化成株式会社 | Photosensitive resin composition and photosensitive resin laminate |
| JP6486672B2 (en) * | 2013-12-20 | 2019-03-20 | 旭化成株式会社 | Photosensitive element and manufacturing method thereof |
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| TW201546547A (en) * | 2014-05-13 | 2015-12-16 | Hitachi Chemical Co Ltd | Photosensitive resin composition, photosensitive element, method of forming resist pattern and method of producing printed circuit board |
| TWI671594B (en) * | 2014-05-13 | 2019-09-11 | 日商日立化成股份有限公司 | Photosensitive resin composition, photosensitive element, method of forming resist pattern and method of producing printed circuit board |
| US10338468B2 (en) | 2014-09-24 | 2019-07-02 | Asahi Kasei Kabushiki Kaisha | Photosensitive resin composition, photosensitive resin laminate, resin pattern production method, cured film, and display device |
| TWI561920B (en) * | 2014-12-22 | 2016-12-11 | Chi Mei Corp | Photosensitive polysiloxane composition, protecting film, and element having the protecting film |
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| CN114437251B (en) * | 2015-04-08 | 2024-02-20 | 旭化成株式会社 | Photosensitive resin composition |
| JP2017003966A (en) * | 2015-06-12 | 2017-01-05 | Jsr株式会社 | Photosensitive composition and method for manufacturing plated molded article |
| KR102443749B1 (en) * | 2015-09-11 | 2022-09-15 | 아사히 가세이 가부시키가이샤 | Photosensitive resin composition |
| WO2017069262A1 (en) * | 2015-10-21 | 2017-04-27 | 日産化学工業株式会社 | Composition for forming optical waveguide |
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| JP6809873B2 (en) * | 2015-12-28 | 2021-01-06 | 旭化成株式会社 | Laminate |
| KR20180077743A (en) * | 2016-12-29 | 2018-07-09 | 주식회사 동진쎄미켐 | Negative photosensitive resin composition |
| TWI664497B (en) * | 2017-01-30 | 2019-07-01 | 日商旭化成股份有限公司 | Photosensitive resin composition, photosensitive resin laminated body, substrate on which photoresist pattern is formed, and method for manufacturing circuit board |
| WO2019035411A1 (en) * | 2017-08-18 | 2019-02-21 | 積水化学工業株式会社 | Moisture curable resin composition, adhesive for electronic components, and adhesive for display elements |
| JP7162448B2 (en) * | 2018-05-29 | 2022-10-28 | 旭化成株式会社 | Photosensitive resin composition, transfer film using photosensitive resin composition, method for producing resin pattern, and method for producing cured film pattern |
| CN114174922A (en) * | 2019-08-06 | 2022-03-11 | 旭化成株式会社 | Photosensitive resin composition and photosensitive element |
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| JPWO2012086371A1 (en) | 2014-05-22 |
| KR20170120190A (en) | 2017-10-30 |
| JP5707420B2 (en) | 2015-04-30 |
| CN103282829A (en) | 2013-09-04 |
| KR20150017384A (en) | 2015-02-16 |
| MY179988A (en) | 2020-11-19 |
| KR20130098406A (en) | 2013-09-04 |
| JP2015096960A (en) | 2015-05-21 |
| TW201232173A (en) | 2012-08-01 |
| TWI530757B (en) | 2016-04-21 |
| WO2012086371A1 (en) | 2012-06-28 |
| KR102019580B1 (en) | 2019-09-06 |
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