CN112585535B - Photosensitive resin composition, method for forming resist pattern, and method for producing plated molded article - Google Patents
Photosensitive resin composition, method for forming resist pattern, and method for producing plated molded article Download PDFInfo
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- CN112585535B CN112585535B CN201980052361.1A CN201980052361A CN112585535B CN 112585535 B CN112585535 B CN 112585535B CN 201980052361 A CN201980052361 A CN 201980052361A CN 112585535 B CN112585535 B CN 112585535B
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- China
- Prior art keywords
- resist pattern
- resin composition
- photosensitive resin
- meth
- acrylate
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- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- -1 thiol compound Chemical class 0.000 claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 238000007747 plating Methods 0.000 claims abstract description 36
- 239000003112 inhibitor Substances 0.000 claims abstract description 35
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 35
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 23
- 239000011347 resin Substances 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 38
- 238000000576 coating method Methods 0.000 claims description 35
- 239000011248 coating agent Substances 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 5
- 230000007261 regionalization Effects 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 66
- 125000003396 thiol group Chemical group [H]S* 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- 230000035945 sensitivity Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LABQKWYHWCYABU-UHFFFAOYSA-N 4-(3-sulfanylbutanoyloxy)butyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCCCOC(=O)CC(C)S LABQKWYHWCYABU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004380 ashing Methods 0.000 description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- SEEVRZDUPHZSOX-UHFFFAOYSA-N [1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=NOC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000004870 electrical engineering Methods 0.000 description 2
- 238000007772 electroless plating Methods 0.000 description 2
- 238000009713 electroplating Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- UCUPUEARJPTGKU-UHFFFAOYSA-N octadecyl 3-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCS UCUPUEARJPTGKU-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RMHRIGGXLCCYHZ-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-1-(1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoronon-1-enoxy)non-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RMHRIGGXLCCYHZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- LSUQRWQGUVIUMU-UHFFFAOYSA-N 1-(2-sulfanylethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound SCCN1C(=O)NC(=O)NC1=O LSUQRWQGUVIUMU-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- BRXKVEIJEXJBFF-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-3-methylbutane-1,4-diol Chemical compound OCC(C)C(CO)(CO)CO BRXKVEIJEXJBFF-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- QSOFJLDXOMMNNK-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O.CC(S)CC(O)=O.CC(S)CC(O)=O.OCC(C)(CO)CO QSOFJLDXOMMNNK-UHFFFAOYSA-N 0.000 description 1
- NKMOLEYVYVWWJC-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis[2-(3-sulfanylbutanoyloxy)ethyl]-1,3,5-triazinan-1-yl]ethyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCN1C(=O)N(CCOC(=O)CC(C)S)C(=O)N(CCOC(=O)CC(C)S)C1=O NKMOLEYVYVWWJC-UHFFFAOYSA-N 0.000 description 1
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SNZYOYGFWBZAQY-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.CCC(CO)(CO)CO SNZYOYGFWBZAQY-UHFFFAOYSA-N 0.000 description 1
- WBEKRAXYEBAHQF-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O.CC(S)CC(O)=O.CC(S)CC(O)=O.CCC(CO)(CO)CO WBEKRAXYEBAHQF-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 102100027123 55 kDa erythrocyte membrane protein Human genes 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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- 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
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- G—PHYSICS
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
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Abstract
The photosensitive resin composition comprises a polymerizable compound (A), a photo-radical polymerization initiator (B), a thiol compound (C) and a polymerization inhibitor (D), wherein the content of the thiol compound (C) is 5 to 50 parts by mass relative to 100 parts by mass of the polymerizable compound (A), and the content of the polymerization inhibitor (D) is 1 to 10 parts by mass relative to 100 parts by mass of the polymerizable compound (A). The present invention provides a photosensitive resin composition having a wide Exposure Latitude (EL) in both bright and dark fields. A method for forming a resist pattern, which enables to form a fine resist pattern with good precision in both bright and dark fields, using a photosensitive resin composition, can be provided. A method for producing a plating pattern, which can produce a fine plating pattern with high accuracy by using a resist pattern formed by a resist pattern formation method, can be provided.
Description
Technical Field
The present invention relates to a photosensitive resin composition, a method for forming a resist pattern, and a method for manufacturing a plated molded article.
Background
In recent years, there has been an increasing demand for high-density mounting of connection terminals such as wires and bumps (bumps) for semiconductor devices, or display devices such as liquid crystal displays and touch panels, and miniaturization has been advanced.
In general, wiring, bumps, and the like are plating shaped articles, and are manufactured by the following methods as described in patent document 1: a photosensitive resin composition is applied to a substrate having a metal foil such as copper, a resist film is formed, the resist film is exposed to light and developed using a mask, a resist pattern is formed, and the substrate is plated using the resist pattern as a mask.
Accordingly, along with miniaturization of wiring, bumps, and the like, miniaturization of resist patterns used for manufacturing the same has been demanded.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2006-285035
Disclosure of Invention
Problems to be solved by the invention
When a negative-type resist film is exposed using a mask, a portion of the resist film where a wiring is densely formed becomes a Bright Field (BF) where the exposure amount is relatively large, and a portion of the resist film where a bump is sparsely formed becomes a Dark Field (Dark Field, DF) where the exposure amount is relatively small.
When the resist pattern is miniaturized, the effects of diffraction of exposure light, light leakage, and reflection of exposure light from the substrate become strong, and the substantial exposure amount (the amount of exposure performed) of the resist coating film differs between the bright field and the dark field. As a result, the following problems occur: in the bright field and the dark field, the accuracy of the formed resist pattern varies. Therefore, the resist coating film requires the following properties: even if the exposure amounts are made to be somewhat different in the bright field and the dark field, the resist pattern is formed with high accuracy in both the bright field and the dark field. That is, a resist composition having a wide common exposure latitude (Exposure Latitude, also simply referred to as "EL") that can form a satisfactory resist pattern in both dark and bright fields and that is repeated in the range of exposure. Here, the Exposure Latitude (EL) refers to a range of exposure that can be formed with high accuracy in a resist pattern.
The purpose of the present invention is to provide a photosensitive resin composition having a wide common Exposure Latitude (EL) in both dark and bright fields, a method for forming a resist pattern capable of forming a fine resist pattern with good precision in both dark and bright fields, and a method for manufacturing a plated molded article capable of forming a fine plated molded article with good precision.
Technical means for solving the problems
The present invention for achieving the object is directed to the following [1] to [8].
[1] A photosensitive resin composition comprising: a polymerizable compound (A), a photo-radical polymerization initiator (B), a thiol compound (C), and a polymerization inhibitor (D), wherein the content of the thiol compound (C) is 5 to 20 parts by mass relative to 100 parts by mass of the polymerizable compound (A), and the content of the polymerization inhibitor (D) is 1 to 5 parts by mass relative to 100 parts by mass of the polymerizable compound (A).
[2] The photosensitive resin composition according to the item [1], wherein the thiol compound (C) is a polyfunctional thiol compound (C-1).
[3] The photosensitive resin composition according to [1] or [2], wherein the content of the polymerization inhibitor (D) is 20 to 80 parts by mass per 100 parts by mass of the thiol compound (C).
[4] The photosensitive resin composition according to any one of [1] to [3], wherein the polymerization inhibitor (D) is a phenolic polymerization inhibitor (D-1).
[5] The photosensitive resin composition according to any one of [1] to [4], wherein the photo radical polymerization initiator (B) is an oxime-based photo radical polymerization initiator (B1).
[6] The photosensitive resin composition according to any one of [1] to [5], which further contains an alkali-soluble resin (E).
[7] A method for forming a resist pattern, comprising: a step (1) of applying the photosensitive resin composition according to any one of [1] to [6] onto a substrate to form a resin coating film; a step (2) of exposing the resin coating film; and (3) developing the exposed resin coating film.
[8] A method for manufacturing a plated molded article, comprising: a step of performing a plating process on the substrate using the resist pattern formed by the method for forming a resist pattern according to [7] as a mask.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention provides a photosensitive resin composition having a wide common Exposure Latitude (EL) in dark and bright fields. A method for forming a resist pattern, which enables to form a fine resist pattern with good precision in both bright and dark fields, using the photosensitive resin composition, can be provided. A method for producing a plating pattern, which can produce a fine plating pattern with excellent accuracy by using a resist pattern formed by the method for forming a resist pattern, can be provided.
Drawings
Fig. 1 is a photograph of an electron microscope of the resist pattern of example 1B, example 2B and comparative example 3B.
FIG. 2 is a photograph of an electron microscope of a plated pattern using a 2 μm 1L/1S resist pattern as a mask at an optimal Exposure (EOP).
Detailed Description
[ Photosensitive resin composition ]
The photosensitive resin composition of the present invention comprises a polymerizable compound (A), a photo-radical polymerization initiator (B), a thiol compound (C), and a polymerization inhibitor (D), wherein the content of the thiol compound (C) is 5 to 50 parts by mass relative to 100 parts by mass of the polymerizable compound (A), and the content of the polymerization inhibitor (D) is 1 to 10 parts by mass relative to 100 parts by mass of the polymerizable compound (A).
The photosensitive resin composition of the present invention has a wide common EL in dark and bright fields.
As described above, if the common EL of the photosensitive resin composition is narrow, the accuracy of the formed resist pattern is likely to vary between bright and dark fields. The reason why the common EL of the photosensitive resin composition is narrowed is considered to be several, and the present inventors focused on (1) that the diffusion length of radicals generated when the photosensitive resin composition is exposed is too long and (2) that the sensitivity of the photosensitive resin composition to exposure light is low.
If the diffusion length of the radicals is long, the radicals generated by exposure are widely diffused in addition to the area (area) irradiated with the exposure light in the resist coating film formed from the photosensitive resin composition, and the radical reaction proceeds beyond the envisaged range, and the accuracy of the resist pattern is lowered. Therefore, it is considered that the exposure range in which a resist pattern with high accuracy can be formed is limited, and the common EL is narrowed. The extent and extent to which the radical reaction proceeds depends on the amount of radical generation and the diffusion length. The amount of radicals generated differs in the bright field and dark field, and therefore, the accuracy of the resist pattern differs in the bright field and dark field.
In addition, if the sensitivity of the photosensitive resin composition to exposure light is low, the exposure amount needs to be increased, and thus the influence of light leakage becomes large. Therefore, it is considered that the degree of low sensitivity affects the common EL.
Therefore, in the present invention, a certain amount of polymerization inhibitor is added to the photosensitive resin composition in order to suppress the diffusion length of the radical. On the other hand, when the polymerization inhibitor is added, the sensitivity is greatly reduced, and therefore, a certain amount of a thiol compound capable of improving the sensitivity, in particular, a polyfunctional thiol compound is added to the photosensitive resin composition. That is, the polymerization inhibitor suppresses the disadvantage caused by the long diffusion length of the radical, and the thiol compound suppresses the disadvantage caused by the sensitivity decrease caused by the addition of the polymerization inhibitor. Further, by adding the polyfunctional thiol, the adhesion between the substrate and the resist coating film is enhanced, and the accuracy of the resist pattern is further improved. As described above, the present invention realizes a wide common EL by the complex effect of the polymerization inhibitor and the thiol compound.
The common EL of the photosensitive resin composition of the present invention is usually 8% or more, preferably 10% or more, and more preferably 15% or more. Therefore, when a resist pattern is formed using the photosensitive resin composition of the present invention, even a fine resist pattern can be formed, the selectable exposure range is wide, and the formation of the resist pattern is easy, and a desired resist pattern can be easily formed in both bright and dark fields.
In the present specification, a region corresponding to the formation of a resist pattern having a1 to 1 line and space (hereinafter, abbreviated as "1L/1S of 2 μm") having a size of 2 μm is referred to as a bright field, and a region corresponding to the formation of a resist pattern having a1 to 3 line and space (hereinafter, abbreviated as "1L/3S of 2 μm") having a size of 2 μm is referred to as a dark field. The common EL represents a ratio of an exposure amount range in which a fine resist pattern can be formed accurately in a bright field to an exposure amount range in which the exposure amount range in which a fine resist pattern can be formed accurately in a dark field is repeated with respect to an optimal exposure amount (hereinafter, also referred to as "EOP") when the exposure amount of a 1L/1S resist pattern of which the thickness is optimally formed to 2 μm is set as the optimal exposure amount.
The polymerizable compound (a) is a component that undergoes radical polymerization by using an active species generated by a photo radical polymerization initiator by exposure, and preferably has at least one ethylenically unsaturated double bond in one molecule.
The polymerizable compound (a) is preferably a (meth) acrylate compound having a (meth) acryloyl group or a compound having a vinyl group. The (meth) acrylate compound is classified into a monofunctional (meth) acrylate compound and a polyfunctional (meth) acrylate compound, and may be any compound.
Examples of the monofunctional (meth) acrylate compound include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl pentyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, glycerol (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, ethylene glycol monoethyl ether (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, methoxyethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, phenoxypolypropylene glycol (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decadienyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decanyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decenyl (meth) acrylate, isobornyl (meth) acrylate, bornyl (meth) acrylate, cyclohexyl (meth) acrylate, acrylamide, methacrylamide, diacetone (meth) acrylamide, isobutoxymethyl (meth) acrylamide, N-dimethyl (meth) acrylamide, t-octyl (meth) acrylamide, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 7-amino-3, 7-dimethyloctyl (meth) acrylate, and the like.
Examples of the polyfunctional (meth) acrylate compound include: trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane propylene oxide (propylene oxide, PO) modified tri (meth) acrylate, tetramethylolpropane tetra (meth) acrylate, ethylene glycol di (meth) acrylate, tetraethyleneglycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, propylene glycol di (meth) acrylate, butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, tri (2-hydroxyethyl) isocyanurate tri (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, epoxy (meth) acrylate formed by adding (meth) acrylic acid to diglycidyl ether of bisphenol A, bisphenol A di (meth) acryloyloxymethyl ether, bisphenol A di (meth) acryloyloxyethyl oxyethyl ether, tri (meth) acrylate, pentaerythritol di (meth) acrylate, polyester (meth) acrylates (trifunctional or more), phthalic acid and epoxy acrylate reactants, and the like.
As the polymerizable compound (A), a commercially available compound can be used as it is. Examples of the commercially available compounds include: sub-Luo Nisi (Aronix) M-210, sub-Luo Nisi (Aronix) M-309, sub-Luo Nisi (Aronix) M-310, sub-Luo Nisi (Aronix) M-320, sub-Luo Nisi (Aronix) M-400, sub-Luo Nisi (Aronix) M-7100, sub-Luo Nisi (Aronix) M-8030, sub-Luo Nisi (Aronix) M-8060, sub-Luo Nisi (Aronix) M-8100, sub-Luo Nisi (Aronix) M-9050, sub-Luo Nisi (Aronix) M-240, sub-Luo Nisi (Aronix) M-245, sub-Luo Nisi (Aronix) M-6100, sub-Luo Nisi (Aronix) M-6200, sub-Luo Nisi (Aronix) M-6250, sub-Luo Nisi (Aronix) M-6300, sub-Luo Nisi (Aronix) M-6400, luo Nisi (Aronix) M-6500 (manufactured above for east Asia Synthesis (Stra)), kayara (KAYARAD) R-551, kayara (KAYARAD) R-712, kayara (KAYARAD) TMPTA, kayara (KAYARAD) HDDA, kayara (KAYARAD) TPGDA, kayara (KAYARAD) PEG400DA, kayara (KAYARAD) MANDA, kayara (KAYARAD) HX-220, kayara (KAYARAD) HX-620, kayara (KAYARAD) R-604, kayara (YAKARAD) DPCA-20, kayara (KAYARAD) DPCA-30, kayara (KAYARAD) DPCA-60, kayara (kayara) DPCA-120 (manufactured above as japan chemical (strand)), bisket (viscot) #295, bisket (viscot) #300, bisket (viscot) #260, bisket (viscot) #312, bisket (viscot) #335HP, bisket (viscot) #360, bisket (viscot) # GPT, bisket (viscot) #3PA, bisket (viscot) #400 (manufactured above as osaka organic chemical industry (strand)), and the like.
These polymerizable compounds (A) may be used singly or in combination of two or more.
The content of the polymerizable compound (a) in the photosensitive resin composition is usually 5 to 90% by mass, preferably 10 to 70% by mass, and more preferably 15 to 50% by mass in the solid content. In the present invention, the term "solid component" refers to all components except the solvent contained in the photosensitive resin composition.
The photo radical polymerization initiator (B) is a compound which generates radicals by irradiation with exposure light and starts radical polymerization of the polymerizable compound (a).
Examples of the photo radical polymerization initiator (B) include: oxime-based compounds, organohalogen compounds, oxydiazole (oxydiazole) compounds, carbonyl compounds, ketal compounds, benzoin compounds, acridine compounds, organic peroxidation compounds, azo compounds, coumarin compounds, azide compounds, metallocene compounds, hexaarylbiimidazole compounds, organoboric acid compounds, disulfonic acid compounds, onium salt compounds, acylphosphine (oxide) compounds. Among these, the oxime-based photo-radical polymerization initiator (B1) is preferable in terms of sensitivity, and a photo-radical polymerization initiator having an oxime ester structure is particularly preferable.
Geometric isomers due to double bonds of oxime can exist in the photo radical polymerization initiator having an oxime ester structure, but these are not distinguished, and either one is contained in the photo radical polymerization initiator (B).
Examples of the photo radical polymerization initiator having an oxime ester structure include photo radical polymerization initiators described in WO2010/146883, japanese patent application laid-open publication No. 2011-132115, japanese patent application laid-open publication No. 2008-506749, japanese patent application laid-open publication No. 2009-519904, and japanese patent application laid-open publication No. 2009-519991.
Specific examples of the photo radical polymerization initiator having an oxime ester structure include: n-benzoyloxy-1- (4-phenylmercaptophenyl) butan-1-one-2-imine, N-ethoxycarbonyloxy-1-phenylpropane-1-one-2-imine, N-benzoyloxy-1- (4-phenylmercaptophenyl) octan-1-one-2-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxacyclopentylmethyloxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine, ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acetyl oxime) and the like.
These photo radical polymerization initiators (B) may be used singly or in combination of two or more.
The content of the photo radical polymerization initiator (B) in the photosensitive resin composition is usually 1 to 40 parts by mass, preferably 3 to 35 parts by mass, more preferably 5 to 30 parts by mass, based on 100 parts by mass of the polymerizable compound (a). If the content of the photo radical polymerization initiator (B) is within the above range, a preferable radical amount can be obtained and excellent resolution can be obtained.
As described above, the thiol compound (C) is a component that contributes to the improvement of sensitivity of the photosensitive resin composition, and realizes a wide common EL in both bright field and dark field by the composite effect with the polymerization inhibitor (D).
The thiol compound (C) may be any of a monofunctional thiol compound and a polyfunctional thiol compound, and is preferably a polyfunctional thiol compound (C-1) in view of further improving the sensitivity of the photosensitive resin composition to exposure light.
The monofunctional thiol compound is a compound having 1 thiol group (mercapto group) in the molecule. Examples of the monofunctional thiol compound include: stearyl 3-mercaptopropionate, and the like.
The polyfunctional thiol compound (C-1) is a compound having 2 or more thiol groups (mercapto groups) in the molecule. The polyfunctional thiol compound is preferably a low molecular compound having a molecular weight of 100 or more, more preferably a molecular weight of 100 to 1,500, and still more preferably 150 to 1,000.
The functional number of the polyfunctional thiol compound (C-1) is preferably 2 to 10, more preferably 2 to 8, and still more preferably 2 to 4. When the number of functional groups is large, the film strength is excellent, and when the number of functional groups is small, the storage stability is excellent. In the case of the above-mentioned range, these can be made to coexist.
As the polyfunctional thiol compound (C-1), an aliphatic polyfunctional thiol compound is preferable. Preferable examples of the aliphatic polyfunctional thiol compound include compounds which contain a combination of an aliphatic hydrocarbon group and-O-, -C (=o) -and in which at least two of the hydrogen atoms of the aliphatic hydrocarbon group are substituted with thiol groups.
The thiol group in the polyfunctional thiol compound (C-1) may be a primary thiol group, a secondary thiol group, or a tertiary thiol group, and is preferably a primary thiol group or a secondary thiol group, more preferably a secondary thiol group, from the viewpoints of sensitivity and chemical resistance. In addition, from the viewpoint of storage stability, a secondary thiol group or a tertiary thiol group is preferable, and a secondary thiol group is more preferable.
Examples of the aliphatic polyfunctional thiol compound include: pentaerythritol tetrakis (3-mercaptobutyrate), 1, 4-bis (3-mercaptobutyryloxy) butane, 1,3, 5-tris (3-mercaptobutyryloxyethyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, trimethylolpropane tris (3-mercaptobutyrate), trimethylolethane tris (3-mercaptobutyrate), trimethylolpropane tris (3-mercaptopropionate), tris [ (3-mercaptopropionyloxy) ethyl ] isocyanurate, pentaerythritol tetrakis (3-mercaptopropionate), tetraethyleneglycol bis (3-mercaptopropionate), dipentaerythritol hexa (3-mercaptopropionate) and the like, and among these pentaerythritol tetrakis (3-mercaptobutyrate), 1, 4-bis (3-mercaptobutyryloxy) butane, 1,3, 5-tris (3-mercaptoethyl) -1,3, 5-triazine-2, 4,6 (1H, 3H) -trione and the like are more preferable.
Examples of the commercial products of the aliphatic polyfunctional thiol compound (C-1) include: carrenz MT-PE-1, carrenz MT-BD-1, carrenz MT-NR-1, TPMB, TEMB (manufactured by Showa Denko electric engineering (stock) above), TMMP, TEMPIC, PEMP, EGMP-4, DPMP (manufactured by Sago chemical industries (stock) above), and the like.
These thiol compounds (C) may be used singly or in combination of two or more. From the standpoint of achieving a wide common EL by the composite effect with the polymerization inhibitor (D), the content of the thiol compound (C) is 5 to 50 parts by mass, preferably 5 to 35 parts by mass, more preferably 5 to 25 parts by mass, relative to 100 parts by mass of the polymerizable compound (a), as described above.
As described above, the polymerization inhibitor (D) is a component that contributes to suppression of the diffusion length of radicals, and realizes wide common EL by the recombination effect with the thiol compound (C). The polymerization inhibitor (D) can also contribute to the improvement of the storage stability of the photosensitive resin composition.
Examples of the polymerization inhibitor (D) include: hydroquinone, monoesters of hydroquinone, N-nitrosodiphenylamine, benzoquinone, phenothiazine, p-methoxyphenol, p-tert-butylcatechol, N-phenylnaphthylamine, 2, 6-di-tert-butyl-p-methylphenol, chloranil (chloranil), pyrogallol (pyrogallol).
As the polymerization inhibitor (D), preferred is a phenol-based polymerization inhibitor CD-1 such as hydroquinone, p-methoxyphenol, catechol, etc.
Examples of the commercial products of the polymerization inhibitor (D) include: yi Lunuo (Irganox) 1010 (manufactured by BASF), quiniopawa (QuinoPower) QS20 (manufactured by kawasaki chemical industry (strands)), and the like.
These polymerization inhibitors (D) may be used singly or in combination of two or more.
From the standpoint of achieving a wide common EL by the compounding effect with the thiol compound (C), the content of the polymerization inhibitor (D) is 1 to 10 parts by mass, preferably 3 to 8 parts by mass, more preferably 4 to 6 parts by mass, relative to 100 parts by mass of the polymerizable compound (a), as described above.
The photosensitive resin composition of the present invention preferably contains an alkali-soluble resin (E). If the photosensitive resin composition contains the alkali-soluble resin (E), the resist can be given resistance to the plating solution, and can be developed with an alkali developer.
The alkali-soluble resin (E) is a resin having a property of being dissolved in an alkaline developer to such an extent that the target development treatment can be performed. Examples of the alkali-soluble resin (E) include: known alkali-soluble resins described in japanese patent application laid-open publication No. 2008-276194, japanese patent application laid-open publication No. 2003-241372, japanese patent application laid-open publication No. 2009-531730, WO2010/001691, japanese patent application laid-open publication No. 2011-123225, japanese patent application laid-open publication No. 2009-222923, japanese patent application laid-open publication No. 2006-243161, and the like. More specifically, examples of the alkali-soluble resin (E) include resins having structural units derived from monomers having an acidic functional group such as (meth) acrylic acid, maleic acid, p-hydroxystyrene, isopropenylphenol, and hydroxyphenyl (meth) acrylate, and structural units derived from other monomers such as styrene, N-phenylmaleimide, N-butyl (meth) acrylate, isobornyl (meth) acrylate, and isobornyl vinyl ether.
The weight average molecular weight (Mw) of the alkali-soluble resin (E) in terms of polystyrene as measured by gel permeation chromatography (Gel Permeation Chromatography, GPC) is usually in the range of 1,000 ～ 1,000,000, preferably 2,000 to 50,000, more preferably 3,000 to 20,000.
In terms of improvement of plating resistance of the resist, the alkali-soluble resin (E) preferably has a phenolic hydroxyl group.
The alkali-soluble resin (E) may be used singly or in combination of two or more.
The content of the alkali-soluble resin (E) is usually 50 to 300 parts by mass, preferably 100 to 250 parts by mass, based on 100 parts by mass of the polymerizable compound (a). When the content of the alkali-soluble resin is within the above range, a resist excellent in plating resistance can be formed.
The photosensitive resin composition of the present invention may contain a solvent, a surfactant, an adhesion promoter, a sensitizer, an inorganic filler, and the like as other components within a range that does not impair the object and characteristics of the present invention.
The photosensitive resin composition of the present invention has improved handleability, easy viscosity adjustment, and improved storage stability by containing a solvent.
As the solvent, there may be mentioned:
alcohols such as methanol, ethanol, and propylene glycol;
Cyclic ethers such as tetrahydrofuran and dioxane;
Glycols such as ethylene glycol and propylene glycol;
alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether;
Alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate;
Aromatic hydrocarbons such as toluene and xylene;
Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and 4-hydroxy-4-methyl-2-pentanone;
Esters such as ethyl acetate, butyl acetate, ethyl ethoxyacetate, ethyl glycolate, ethyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-3-methylbutyrate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, and ethyl lactate;
N-methylformamide, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzyl ether, dihexyl ether, acetonylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, gamma-butyrolactone, ethylene carbonate, propylene carbonate, phenylcellosolve acetate, and the like.
The solvent may be used alone or in combination of two or more.
When forming a resist pattern having a film thickness of 0.1 to 100. Mu.m, the solvent content may be such that the solid content of the photosensitive resin composition is 5 to 80 mass%.
The photosensitive resin composition of the present invention can be produced by uniformly mixing the above-mentioned components.
[ Method of Forming resist Pattern ]
The method for forming a resist pattern of the present invention comprises: a step (1) of coating the photosensitive resin composition on a substrate to form a resin coating film; a step (2) of exposing the resin coating film; and (3) developing the exposed resin coating film.
In the step (1), the photosensitive resin composition is coated on a substrate to form a resin coating film.
The substrate is not particularly limited as long as it is a substrate on which the resin coating film can be formed, and examples thereof include: semiconductor substrates, glass substrates, silicon substrates, substrates formed by providing various metal films on the surfaces of semiconductor plates, glass plates, silicon plates, and the like. The shape of the substrate is not particularly limited. The shape may be a flat plate, or may be a shape in which a concave portion (hole) is provided in a flat plate like a silicon wafer. In the case of a substrate having a recess and further having a copper film on the surface, the copper film may be provided at the bottom of the recess, as in a Through-Silicon-Via (TSV) structure.
The method of applying the photosensitive resin composition is not particularly limited, and for example, a spray method, a roll coating method, a spin coating method, a slot die coating method, a bar coating method, and an inkjet method can be used, and spin coating is particularly preferred. In the case of spin coating, the spin speed is usually 800 to 3000rpm, preferably 800 to 2000rpm, and the spin time is usually 1 to 300 seconds, preferably 5 to 200 seconds. After spin-coating the photosensitive resin composition, the obtained coating film is dried by heating at 50 to 250 ℃ for about 1 to 30 minutes, for example.
The film thickness of the resin coating film is usually 0.1 μm to 300. Mu.m, preferably 1 μm to 100. Mu.m, and is usually 0.1 μm to 50. Mu.m when the plated molded article is a wiring, and is usually 1 μm to 300. Mu.m when the plated molded article is a bump electrode. Since the influence of oxygen inhibition becomes more remarkable as the film thickness of the resin coating film becomes thin, the film thickness is preferably set to the above range in the case of producing a plated molded article.
In the step (2), the resin coating film is exposed to light. That is, the resin coating film is selectively exposed in such a manner that a resist pattern is obtained in step (3).
With respect to selective exposure, the coating film is typically exposed using, for example, a contact aligner (contact aligner), stepper (steppers) or scanner (scanner) with the required photomask interposed therebetween. As the exposure light, light having a wavelength of 200nm to 500nm (for example, i-ray (365 nm)) is generally used. The exposure amount varies depending on the type of the component in the coating film, the blending amount, the thickness of the coating film, and the like, and is usually 1mJ/cm 2～10,000mJ/cm2 when the exposure light is i-rays.
As described above, since the photosensitive resin composition used for forming the resin coating film has a wide common EL in both the dark field and the bright field, even when a fine resist pattern having the bright field and the dark field in the step (2) is formed, a satisfactory resist pattern can be formed.
In addition, the heat treatment may be performed after the exposure. The conditions of the heat treatment after exposure may be appropriately determined depending on the types of components in the resin coating film, the blending amount, the thickness of the coating film, and the like, and are usually 70 to 180℃for 1 to 60 minutes.
In the step (3), the resin coating film after exposure is developed. Thereby, a resist pattern is formed.
As the developer, for example, usable are: sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, dimethylethanolamine, triethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyrrole, piperidine, 1, 8-diazabicyclo [5.4.0] -7-undecene, 1, 5-diazabicyclo [4.3.0] -5-nonene in aqueous solution. In addition, an aqueous solution obtained by adding a proper amount of a water-soluble organic solvent such as methanol or ethanol or a surfactant to the aqueous solution of the alkali may be used as the developer.
The development time varies depending on the type of each component in the composition, the blending ratio, the thickness of the coating film, and the like, and is usually 30 seconds to 600 seconds. The developing method may be any one of a liquid coating method, a dipping (dipping) method, a puddle (puddle) method, a spraying method, a spray developing method, and the like.
The resist pattern produced as described above can be further cured by additional exposure (hereinafter referred to as "post exposure") or heating depending on the application.
Post-exposure can be performed using the same method as the exposure. The exposure amount is not particularly limited, and in the case of using a high-pressure mercury lamp, it is preferably 100mJ/cm 2～10,000mJ/cm2. The heating may be performed at a predetermined temperature, for example, 60 to 200 ℃ for a predetermined time using a heating device such as a hot plate or an oven, for example, if the heating device is on the hot plate, the heating is performed for 5 to 30 minutes, and if the heating device is in the oven, the heating is performed for 5 to 60 minutes. By the post-treatment, a cured film having a pattern with good characteristics can be further obtained.
The resist pattern may be cleaned with running water or the like. Thereafter, the mixture may be air-dried using an air gun or the like, or may be dried under heating by a hot plate, an oven or the like.
[ Method for producing plated molded article ]
The method for producing a plated molded article of the present invention comprises: and a step of plating the substrate using the resist pattern formed by the method of forming the resist pattern as a mask.
Examples of the plating pattern include bumps and wirings.
The resist pattern is formed according to the method of forming a resist pattern.
As the plating treatment, there may be mentioned: wet plating such as electroplating, electroless plating and melt plating; dry plating such as chemical vapor deposition and sputtering. In the case of forming wiring or connection terminals in the processing of the product chip scale (WAFER LEVEL), the plating treatment is generally performed by an electroplating treatment.
Before the plating process, the inner wall surface of the resist pattern may be subjected to pretreatment such as ashing (ashing) treatment, flux (flux) treatment, and desmear (desmear) treatment in order to improve the affinity between the inner wall surface of the resist pattern and the plating solution.
In the case of the plating treatment, a layer formed on the inner wall of the resist pattern by sputtering or electroless plating treatment can be used as a seed layer, and in the case of using a substrate having a metal film on the surface thereof as a substrate, the metal film can also be used as a seed layer.
The barrier layer may also be formed prior to forming the seed layer, and the seed layer can also be used as a barrier layer.
Examples of the plating solution used for the plating treatment include: a copper plating solution containing copper sulfate, copper pyrophosphate, or the like; a gold plating solution comprising potassium gold cyanide; a nickel plating solution comprising nickel sulfate or nickel carbonate.
The conditions of the plating treatment may be appropriately selected depending on the type of plating solution, etc., and for example, in the case of a plating treatment comprising copper sulfate, the temperature is usually 10 to 90℃and the current density is 0.1A/dm 2～100A/dm2.
As for the plating process, different plating processes may be sequentially performed. For example, a copper plating process is performed first, followed by a nickel plating process, followed by a molten solder plating process, whereby solder copper pillar bumps can be formed.
The thickness of the plated molded article varies depending on the application, and is usually 1 μm to 300 μm in the case of bump electrodes, and is usually 0.1 μm to 50 μm in the case of wirings, for example.
Since the resist pattern is formed by using the photosensitive resin composition, a desired resist pattern can be easily formed even in a fine resist pattern. Therefore, in the method for producing a plated molded article of the present invention using a resist pattern formed by the method for forming a resist pattern, a fine plated molded article can be produced with high accuracy and in a simple manner.
Examples
The present invention will be specifically described below based on examples, but the present invention is not limited to these examples. In the following description of examples and the like, "parts" are used in the meaning of "parts by mass".
The weight average molecular weight (Mw) of the alkali-soluble resin is a value calculated by converting polystyrene by gel permeation chromatography under the following conditions.
Tubular column: the columns TSK-M and TSK2500 manufactured by Tosoh Co., ltd were connected in series.
Solvent: tetrahydrofuran (THF)
Column temperature: 40 DEG C
Detection method: refractive index method
Standard substance: polystyrene
GPC apparatus: manufactured by Tosoh Co., ltd., apparatus name "HLC-8220-GPC"
< Production of photosensitive resin composition >
[ Example 1A to example 8A, and comparative example 1A to comparative example 7A ]
The photosensitive resin compositions of examples 1A to 8A and comparative examples 1A to 7A were produced by adding each component in the amounts shown in table 1 below to the solvent so that the solid content concentration became 55 mass% using propylene glycol monomethyl ether acetate as the solvent, mixing the components, and filtering the mixture by a capsule filter (pore size: 3 μm). Details of the components shown in table 1 are as follows.
Polymerizable compound (A1): polyester acrylic acid ester (product name "Asia Luo Nisi (Aronix) M-8060", manufactured by east Asia Synthesis (Strand))
Photo radical polymerization initiator (B1): a compound represented by the following formula (B1)
[ Chemical 1]
Photo radical polymerization initiator (B2): 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide
Thiol compound (C1): pentaerythritol tetrakis (3-mercaptobutyrate) (product name "Carrenz (Karenz) MT PE1", manufactured by Zhaoand electrical engineering (stock))
Thiol compound (C2): stearyl 3-mercaptopropionate (product name "STMP", manufactured by Sakai chemical industry (Strand))
Thiol compound (C3): 1, 4-bis (3-mercaptobutyryloxy) butane (product name "Karenz" MT-BD-1", manufactured by Zhaowa electric (stock))
Thiol compound (C4): 1,3, 5-tris (2- (3-mercaptobutyryloxy) ethyl) -1,3, 5-triazacyclohexane-2, 4, 6-dione (manufactured by Karenz MT-NR-1", zhaokogaku electrical engineering (stock))
Polymerization inhibitor (D1): hindered phenol polymerization inhibitor (product name "Yi Lunuo si (Irganox) 1010", manufactured by BASF corporation)
Polymerization inhibitor (D2): phenolic polymerization inhibitor (product name "quiniepawa (QuinoPower) QS20", manufactured by kawasaki chemical industry (stock))
Polymerization inhibitor (D3): p-benzoquinone
Polymerization inhibitor (D4): phenothiazines
Alkali-soluble resin (E1): acrylic resin having structural units with symbols a to c represented by the following formula (E1) (Mw: 8000, content ratio of structural units a to c: a/b/c=50/30/20 (% by mass))
[ Chemical 2]
Surfactant (F1): diglycerol ethylene oxide (average addition mole number: 18) adduct perfluorononenyl ether (product name "Fujiett (Ftergent) FTX-218", manufactured by Nieuse (NEOS) (Strand))
TABLE 1
< Formation of resist Pattern >
Example 1B
The photosensitive resin composition of example 1A was applied to a substrate provided with a copper sputtered film on a 6-inch silicon wafer by spin coating, and heated at 110 ℃ for 180 seconds by a hot plate to form a resin coating film having a film thickness of 12 μm.
The resin coating film was exposed using a stepper for i-ray exposure (device name "NSR-i12D", manufactured by Nikon (strands)), via a photomask having a region corresponding to 2 μm of 1L/1S resist pattern formation (hereinafter referred to as "BF corresponding region") and a region corresponding to 2 μm of 1L/3S resist pattern formation (hereinafter referred to as "DF corresponding region"). With respect to exposure, shots (shots) of increasing 10mJ/cm 2 each time were made from 20mJ/cm 2 up to 260mJ/cm 2.
Using 2.38 mass% tetramethyl ammonium hydroxide water as a developer, the exposed resin coating film was developed by a liquid-coating method, and then washed with running water and dried to form a resist pattern.
By observing the resist pattern with an electron microscope, an optimal exposure amount (EOP) which is an exposure amount of a 1L/1S resist pattern of 2 μm which is optimally formed in a BF-corresponding region, an exposure amount range in which a fine resist pattern can be precisely formed in BF, an exposure amount range in which a fine resist pattern can be precisely formed in DF, and an exposure amount range (repetitive exposure amount range) in which the exposure amount range in BF and the exposure amount range in DF are repeated are obtained.
Further, the common EL of BF and DF is calculated from the ratio of the repetitive exposure amount range to the EOP.
The evaluation results are shown in table 2. Fig. 1 shows a photograph of an electron microscope of example 1B.
TABLE 2
[ Examples 2B to 8B, comparative examples 1B to 7B ]
In example 1B, a resist pattern was formed in the same manner as in example 1B except that the photosensitive resin compositions shown in table 2 were used, and the exposure amount ranges and the repeat exposure amount ranges in the BF-corresponding region and the DF-corresponding region, and the common EL were measured. The evaluation results are shown in table 2.
Fig. 1 shows photographs of electron microscopes of example 2B and comparative example 3B.
< Production of plated molded article >
Example 1C
The substrate having the resist pattern formed in example 1B was subjected to ashing treatment. The ashed substrate was immersed in1 liter of a copper plating solution (product name "Microb Cu300", manufactured by EEJA corporation) at 25℃for 15 minutes to carry out a plating reaction. Then, the resist pattern was peeled off using a resist peeling liquid (product name "Emotion park (ELPAC) THB-S17", manufactured by JSR (stock)), to manufacture a plating pattern.
FIG. 2 is a photograph of an electron microscope of a plated pattern using a2 μm 1L/1S resist pattern as a mask at EOP.
Claims (5)
1. A photosensitive resin composition characterized by comprising: a polymerizable compound (A), a photo-radical polymerization initiator (B), a thiol compound (C), and a polymerization inhibitor (D), wherein the content of the thiol compound (C) is 5 to 50 parts by mass relative to 100 parts by mass of the polymerizable compound (A), the content of the polymerization inhibitor (D) is 1 to 10 parts by mass relative to 100 parts by mass of the polymerizable compound (A), the content of the polymerization inhibitor (D) is 20 to 80 parts by mass relative to 100 parts by mass of the thiol compound (C), the thiol compound (C) is a polyfunctional thiol compound (C-1), and the polymerization inhibitor (D) is a phenolic polymerization inhibitor (D-1).
2. The photosensitive resin composition according to claim 1, wherein the photo radical polymerization initiator (B) is an oxime-based photo radical polymerization initiator (B1).
3. The photosensitive resin composition according to claim 1 or 2, further comprising an alkali-soluble resin (E).
4. A method for forming a resist pattern, comprising: a step (1) of applying the photosensitive resin composition according to any one of claims 1 to 3 onto a substrate to form a resin coating film; a step (2) of exposing the resin coating film; and (3) developing the exposed resin coating film.
5. A method for manufacturing a plated molded article, characterized by comprising: a step of plating the substrate using the resist pattern formed by the method for forming a resist pattern according to claim 4 as a mask.
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