JP2017211571A - 感光性樹脂組成物、感光性エレメント、半導体装置及びレジストパターンの形成方法 - Google Patents
感光性樹脂組成物、感光性エレメント、半導体装置及びレジストパターンの形成方法 Download PDFInfo
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- JP2017211571A JP2017211571A JP2016105970A JP2016105970A JP2017211571A JP 2017211571 A JP2017211571 A JP 2017211571A JP 2016105970 A JP2016105970 A JP 2016105970A JP 2016105970 A JP2016105970 A JP 2016105970A JP 2017211571 A JP2017211571 A JP 2017211571A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 101
- 238000000034 method Methods 0.000 title claims description 47
- 239000004065 semiconductor Substances 0.000 title claims description 19
- -1 methylol group Chemical group 0.000 claims abstract description 116
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 229920005989 resin Polymers 0.000 claims abstract description 57
- 239000011347 resin Substances 0.000 claims abstract description 57
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 12
- 150000007824 aliphatic compounds Chemical class 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 9
- 125000006544 oxetanylalkyl group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 34
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- 239000011248 coating agent Substances 0.000 claims description 10
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- 229910000077 silane Inorganic materials 0.000 description 13
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- 125000000962 organic group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000012965 benzophenone Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
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- 229910000679 solder Inorganic materials 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 4
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 125000005409 triarylsulfonium group Chemical group 0.000 description 4
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
- NEBBLNDVSSWJLL-UHFFFAOYSA-N 2,3-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(OC(=O)C(C)=C)COC(=O)C(C)=C NEBBLNDVSSWJLL-UHFFFAOYSA-N 0.000 description 3
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical class C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 3
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 3
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-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
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
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- 239000008213 purified water Substances 0.000 description 3
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
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- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical class CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
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- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
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- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
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- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
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- LPQBQAXHOAEOAX-UHFFFAOYSA-N C=1C=C(C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1SC(C=C1)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1SC(C=C1)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 LPQBQAXHOAEOAX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
- KGBBDBRJXGILTQ-UHFFFAOYSA-N [3-(2-methylprop-2-enoyloxy)-2,2-bis(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(COC(=O)C(C)=C)(COC(=O)C(C)=C)COC(=O)C(C)=C KGBBDBRJXGILTQ-UHFFFAOYSA-N 0.000 description 2
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000007611 bar coating method Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- QRGRKKPOHDZVIH-UHFFFAOYSA-N bis(2,4-diethoxyphenyl)methanone Chemical compound C(C)OC1=C(C(=O)C2=C(C=C(C=C2)OCC)OCC)C=CC(=C1)OCC QRGRKKPOHDZVIH-UHFFFAOYSA-N 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
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- UMIKAXKFQJWKCV-UHFFFAOYSA-M diphenyliodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C=1C=CC=CC=1[I+]C1=CC=CC=C1 UMIKAXKFQJWKCV-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
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- 238000007772 electroless plating Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- MABAWBWRUSBLKQ-UHFFFAOYSA-N ethenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C=C MABAWBWRUSBLKQ-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
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- DRXHEPWCWBIQFJ-UHFFFAOYSA-N methyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C)OC1=CC=CC=C1 DRXHEPWCWBIQFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
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- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
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- 125000003566 oxetanyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
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- RQCQDYRSQKDVED-UHFFFAOYSA-N phenyl-(4-phenylphenyl)-[4-(4-phenylphenyl)sulfanylphenyl]sulfanium Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1[S+](C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 RQCQDYRSQKDVED-UHFFFAOYSA-N 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
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- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
本実施形態の感光性樹脂組成物は、(A)成分:一般式(1)で表される構造単位を有するアルカリ可溶性樹脂と、(B)成分:光感応性酸発生剤と、(C)成分:芳香環、複素環及び脂環からなる群より選ばれる少なくとも1種を有し、かつ、メチロール基又はアルコキシアルキル基を有する化合物と、(D)成分:アクリロイルオキシ基、メタクリロイルオキシ基、グリシジルオキシ基及び水酸基からなる群より選ばれる少なくとも1種の官能基を2つ以上有する脂肪族化合物と、を含有する。なお、本明細書において、これらの成分は、単に(A)成分、(B)成分、(C)成分、(D)成分等と称することがある。
(A)成分は、下記一般式(1)で表される構造単位を有するアルカリ可溶性樹脂である。
使用機器:日立L−6000型〔株式会社日立製作所製〕
カラム:ゲルパックGL−R420+ゲルパックGL−R430+ゲルパックGL−R440〔日立化成株式会社 商品名、計3本〕
溶離液:テトラヒドロフラン
測定温度:40℃
流量:1.75ml/min.
検出器:L−3300RI〔株式会社日立製作所製〕
(B)成分である光感応性酸発生剤は、活性光線等の照射によって酸を発生する化合物である。該(B)成分から発生する酸の触媒効果により、(C)成分中のメチロール基同士若しくはアルコキシアルキル基同士、又は、(C)成分中のメチロール基若しくはアルコキシアルキル基と(A)成分とが脱アルコールを伴って反応することによって現像液に対する組成物の溶解性が大幅に低下し、ネガ型のパターンを形成することができる。
(C)成分は、芳香環、複素環及び脂環からなる群より選ばれる少なくとも1種を有し、かつ、メチロール基又はアルコキシアルキル基を有する化合物である。ここで、芳香環とは、芳香族性を有する炭化水素基(例えば、炭素原子数が6〜10の炭化水素基)を意味し、例えば、ベンゼン環及びナフタレン環が挙げられる。複素環とは、窒素原子、酸素原子、硫黄原子等を少なくとも1つ有する環状基(例えば、炭素原子数が3〜10の環状基)を意味し、例えば、ピリジン環、イミダゾール環、ピロリジノン環、オキサゾリジノン環、イミダゾリジノン環及びピリミジノン環が挙げられる。また、脂環とは、芳香族性を有しない環状炭化水素基(例えば、炭素原子数が3〜10の環状炭化水素基)を意味し、例えば、シクロプロパン環、シクロブタン環、シクロペンタン環及びシクロヘキサン環が挙げられる。アルコキシアルキル基とは、アルキル基が酸素原子を介してアルキル基に結合した基を意味する。また、2つのアルキル基は互いに異なってもよく、例えば、炭素原子数が1〜10であるアルキル基であってもよい。
(D)成分は、アクリロイルオキシ基、メタクリロイルオキシ基、グリシジルオキシ基、オキセタニルアルキルエーテル基、ビニルエーテル基及び水酸基からなる群より選ばれる少なくとも1種の官能基を2つ以上有する脂肪族化合物である。(D)成分は、上記官能基を3つ以上有する脂肪族化合物を含むことが好ましい。上記官能基数の上限は、特に制限はないが、例えば、12個である。
本実施形態の感光性樹脂組成物は、(E)成分として、ベンゾフェノン化合物を含有してもよい。感光性樹脂組成物が(E)成分を含有することにより、感光性樹脂組成物の解像性をより向上させることができ、微細なレジストパターンが形成可能な露光量の裕度を向上することができ、生産性がより向上できる。ベンゾフェノン化合物としては、ベンゾフェノン、4,4’−ジアミノベンゾフェノン、4,4’−ビス(ジメチルアミノ)ベンゾフェノン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、4,4’−ビス(ジブチルアミノ)ベンゾフェノン、4−エチルアミノベンゾフェノン、2,4−ジヒドロキシベンゾフェノン、3,4−ジヒドロキシベンゾフェノン、2,3,4−トリヒドロキシベンゾフェノン、2,3,4,4’−テトラヒドロキシベンゾフェノン、2,2’,4,4’−テトラヒドロキシベンゾフェノン、2,2’,4,4’−テトラメトキシベンゾフェノン、2,2’,4,4’−テトラエトキシベンゾフェノン、2,2’,4,4’−テトラブトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジエトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジブトキシベンゾフェノン、4,4’−ジヒドロキシベンゾフェノン、4,4’−ジメトキシベンゾフェノン、4,4’−ジブトキシベンゾフェノン、4,4’−ジフェニルベンゾフェノン等が挙げられる。
本実施形態の感光性樹脂組成物は、(F)成分として、溶剤を更に含有することもできる。感光性樹脂組成物が(F)成分を含有することにより、感光性樹脂組成物の取り扱い性がより向上し、粘度及び保存安定性をより調節し易くなる。(F)成分は、有機溶剤であることが好ましい。有機溶剤は、上記性能を発揮できるものであれば特に制限はないが、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート;プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル等のプロピレングリコールモノアルキルエーテル;プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジプロピルエーテル、プロピレングリコールジブチルエーテル等のプロピレングリコールジアルキルエーテル;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート;エチルセロソルブ、ブチルセロソルブ等のセロソルブ;ブチルカルビトール等のカルビトール;乳酸メチル、乳酸エチル、乳酸n−プロピル、乳酸イソプロピル等の乳酸エステル;酢酸エチル、酢酸n−プロピル、酢酸イソプロピル、酢酸n−ブチル、酢酸イソブチル、酢酸n−アミル、酢酸イソアミル、プロピオン酸イソプロピル、プロピオン酸n−ブチル、プロピオン酸イソブチル等の脂肪族カルボン酸エステル;3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、ピルビン酸メチル、ピルビン酸エチル等のエステル;トルエン、キシレン等の芳香族炭化水素;2−ブタノン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、シクロヘキサノン等のケトン;N,N−ジメチルホルムアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルピロリドン等のアミド;γ−ブチロラクトン等のラクトンなどが挙げられる。(F)成分は、1種単独又は2種以上を混合して使用することができる。
本実施形態の感光性樹脂組成物は、(G)成分として、シロキサン結合を有する化合物((A)〜(F)成分に該当する化合物を除く)を含有してもよい。(G)成分としては、シロキサン結合を有していれば特に限定されないが、例えば、シロキサン結合を有する無機フィラー、シロキサン結合を有するシラン化合物及びアルコキシオリゴマーが挙げられる。(G)成分は、1種単独又は2種以上を混合して使用することができる。
(R101O)4−f−Si−(R102)f …(17)
一般式(17)中、R101は、メチル基、エチル基、プロピル基等の炭素数が1〜10であるアルキル基を示し、R102は、1価の有機基を示し、fは、0〜3の整数を示す。fが0、1又は2の場合、複数のR101は互いに同一でも異なっていてもよい。fが2又は3の場合、複数のR102は互いに同一でも異なっていてもよい。R101は、解像性に更に優れる観点で、炭素数が1〜5のアルキル基が好ましく、炭素数が1又は2のアルキル基がより好ましい。無機フィラーの分散性を向上させるためにシラン化合物で処理する場合、無機フィラーの分散性を更に向上させる観点で、fは0、1又は2が好ましく、0又は1がより好ましい。
本実施形態の感光性樹脂組成物は、(H)成分として、増感剤を更に含有していてもよい。感光性樹脂組成物が(H)成分を含有することにより、感光性樹脂組成物の感度を更に向上させることができる。増感剤としては、9,10−ジブトキシアントラセン等が挙げられる。(E)成分は、1種単独又は2種以上を混合して使用することができる。
本実施形態の感光性樹脂組成物は、(A)成分に加えて、分子量が1000未満であるフェノール性低分子化合物(以下、「フェノール化合物(a)」という)を含有していてもよい。フェノール化合物(a)としては、4,4’−ジヒドロキシジフェニルメタン、4,4’−ジヒドロキシジフェニルエーテル、トリス(4−ヒドロキシフェニル)メタン、1,1−ビス(4−ヒドロキシフェニル)−1−フェニルエタン、トリス(4−ヒドロキシフェニル)エタン、1,3−ビス[1−(4−ヒドロキシフェニル)−1−メチルエチル]ベンゼン、1,4−ビス[1−(4−ヒドロキシフェニル)−1−メチルエチル]ベンゼン、4,6−ビス[1−(4−ヒドロキシフェニル)−1−メチルエチル]−1,3−ジヒドロキシベンゼン、1,1−ビス(4−ヒドロキシフェニル)−1−[4−{1−(4−ヒドロキシフェニル)−1−メチルエチル}フェニル]エタン、1,1,2,2−テトラ(4−ヒドロキシフェニル)エタン等が挙げられる。これらのフェノール化合物(a)の含有量は、(A)成分100質量部に対して、例えば、0〜40質量部(特に0〜30質量部)の範囲である。
次に、本実施形態の感光性エレメントについて説明する。
次に、本実施形態のレジストパターンの形成方法を説明する。第1実施形態のレジストパターンの形成方法は、上記感光性樹脂組成物を基材(例えば基板)上に塗布し、上記感光性樹脂組成物を乾燥して感光層を形成する工程と、上記感光層を所定のパターンに露光し、露光後加熱処理(露光後ベーク)を行う工程と、上記加熱処理(露光後ベーク)後の上記感光層を現像し、得られた樹脂パターンを加熱処理する工程と、を含む。第2実施形態のレジストパターンの形成方法は、上記感光性エレメントの上記感光層を基材(例えば基板)上に配置する工程と、上記感光層を所定のパターンに露光し、露光後加熱処理(露光後ベーク)を行う工程と、上記加熱処理(露光後ベーク)後の上記感光層を現像し、得られた樹脂パターンを加熱処理する工程と、を含む。
本実施形態に係る半導体装置は、本実施形態に係る感光性樹脂組成物の硬化物を備えている。本実施形態の感光性樹脂組成物の硬化物は、例えば、半導体素子の表面保護膜及び/又は層間絶縁膜、あるいは、多層プリント配線板におけるソルダーレジスト及び/又は層間絶縁膜として好適に用いることができる。
樹脂成分(A−1)〜(A−5)と、光感応性酸発生剤(B−1)と、アルコキシアルキル化合物(C−1)と、アクリロイルオキシ基を有する化合物(D−1)と、ベンゾフェノン化合物(E−1)と、溶剤(F−1)と、シロキサン結合を有する化合物(G−1)とを、表1に示した配合量(単位:質量部)にて配合し、感光性樹脂組成物を得た。
A−1:下記式で表される構造単位を有するフェノール樹脂CST:p−ヒドロキシスチレン−スチレン共重合体(丸善石油化学株式会社製、商品名:マルカリンカー CST−70、Mw10000)
A−2:CST:p−ヒドロキシスチレン−スチレン共重合体(丸善石油化学株式会社製、商品名:マルカリンカー CST−85、Mw10000)
A−3:CMM:p−ヒドロキシスチレン−メチルメタクリル酸共重合体(丸善石油化学株式会社製、商品名:マルカリンカー CMM−70、Mw10000)
A−4:ノボラック樹脂(旭有機材工業株式会社製、商品名:TR4080G、Mw5000)
A−5:ノボラック樹脂(旭有機材工業株式会社製、商品名:TR4020G、Mw15000)
B−1:トリアリールスルホニウム塩(サンアプロ株式会社製、商品名:CPI−310B)
C−1:1,3,4,6−テトラキス(メトキシメチル)グリコールウリル(株式会社三和ケミカル製、商品名:MX−270)
D−1:ペンタエリスリトールトリアクリレート(日本化薬株式会社製、商品名:PET−30)
E−1:4,4’−ビス(ジエチルアミノ)ベンゾフェノン(保土谷化学工業株式会社製、商品名:EAB)
F−1:メチルエチルケトン(和光純薬工業株式会社製、商品名:2−ブタノン)
G−1:3−グリシドキシプロピルトリメトキシシラン(信越化学工業株式会社製、商品名:KBM−403)
直径6インチの銅めっき膜を付けたシリコンウェハ(アドバンスマテリアルズテクノロジー株式会社製、商品名:6インチCuメッキ15000Åウェハ)上に、上記感光性エレメントの保護層を剥がした後、該感光性エレメントをラミネートし、積層体を得た。ラミネート工程は、真空加圧式ラミネータを用いて、60℃のヒータ(上側)、60℃のヒータ(下側)、20秒の真空引き時間、20秒の加圧時間、0.4MPaの圧着圧力で行った。次いで、上記積層体の支持体を剥がし、i線ステッパー(キヤノン株式会社製、商品名:FPA−3000iW)を用いてi線(365nm)で、マスクを介して、感光層に対して縮小投影露光を行った。マスクとしては、ビア直径1〜30μmまで1μm刻みでビア開口部(未露光部)を有するネガパターンを用いた。また、露光量は、100〜2000mJ/cm2の範囲で、100mJ/cm2ずつ変化させながら縮小投影露光を行った。
厚さ1mmのガラス板上に、上記感光性エレメントの保護層を剥がした後、該感光性エレメントをラミネートし、積層体を得た。ラミネート工程は、真空加圧式ラミネータを用いて、60℃のヒータ(上側)、60℃のヒータ(下側)、20秒の真空引き時間、20秒の加圧時間、0.4MPaの圧着圧力で行った。上記積層体の支持体を剥がし、プロキシミティー露光機(ウシオ電機株式会社製、商品名:UX−1000SM)を用いて露光量1000mJ/cm2で露光を行い、65℃で1分間、次いで75℃で8分間加熱して(露光後ベーク)、露光後の感光層を硬化させた。その後、感光層を更に180℃で60分間加熱硬化させ、感光性樹脂組成物の硬化膜を得た。得られた硬化膜をガラス板とともに23℃において精製水に24時間浸漬し、浸漬前後における重量を測定し、下記式(a)により吸水率を求めた。
吸水率(%)=(浸漬後の硬化膜の重量−浸漬前の硬化膜の重量)/(浸漬前の硬化膜の重量)×100 …(a)
上記感光性樹脂組成物をポリエチレンテレフタレートフィルム(帝人デュポンフィルム株式会社製、商品名:ピューレックスA53)(支持体)上に厚さが均一になるように塗布し、90℃の熱風対流式乾燥機で10分間乾燥して、乾燥後の厚さが40μmである感光層を形成した。次いで、支持体を剥離して、高圧水銀灯を有する露光機(株式会社オーク製作所製、商品名:EXM−1201)を用いて、照射エネルギー量が1000mJ/cm2となるように感光層を露光した。露光された感光層をホットプレート上にて65℃で2分間、次いで95℃で8分間加熱し、熱風対流式乾燥機にて180℃で60分間加熱処理をし、硬化膜を得た。卓上形精密万能試験機(株式会社島津製作所製、商品名:オートグラフAGS−H100N)を用いて、引っ張り速度5mm/分、測定温度20℃〜25℃、荷重3〜5Nの条件における硬化膜のひずみ変化(弾性率)を測定した。なお、試料として使用した硬化膜の幅は10mm、厚さは9〜11μmであり、チャック間幅は20mmとした。
6インチのシリコンウェハ上に、上記感光性エレメントの保護層を剥がした後、該感光性エレメントをラミネートし、積層体を得た。ラミネート工程は、真空加圧式ラミネータを用いて、60℃のヒータ(上側)、60℃のヒータ(下側)、20秒の真空引き時間、20秒の加圧時間、0.4MPaの圧着圧力で行った。上記積層体の支持体を剥がし、プロキシミティー露光機(ウシオ電機株式会社製、商品名:UX−1000SM)を用いて露光量1000mJ/cm2で露光を行い、65℃で1分間、次いで75℃で8分間加熱して(露光後ベーク)、露光後の感光層を硬化させた。その後、感光層を更に180℃で60分間加熱硬化させ、感光性樹脂組成物の硬化膜を得た。薄膜ストレス測定装置(テンコール社製)を用いて、得られた硬化膜のウェハ応力を測定した。
Claims (7)
- (A)成分:下記一般式(1)で表される構造単位を有するアルカリ可溶性樹脂と、
(B)成分:光感応性酸発生剤と、
(C)成分:芳香環、複素環及び脂環からなる群より選ばれる少なくとも1種を有し、かつ、メチロール基又はアルコキシアルキル基を有する化合物と、
(D)成分:アクリロイルオキシ基、メタクリロイルオキシ基、グリシジルオキシ基、オキセタニルアルキルエーテル基、ビニルエーテル基及び水酸基からなる群より選ばれる少なくとも1種の官能基を2つ以上有する脂肪族化合物と、を含有する、感光性樹脂組成物。
[式(1)中、R1は水素原子又はメチル基を示し、R2は炭素数1〜10のアルキル基、炭素数6〜10のアリール基又は炭素数1〜10のアルコキシ基を示し、aは0〜3の整数を示し、bは1〜3の整数を示す。] - 前記(D)成分の含有量が、前記(A)成分100質量部に対して、1〜70質量部である、請求項1に記載の感光性樹脂組成物。
- (G)成分:シロキサン結合を有する化合物を更に含有する、請求項1又は2に記載の感光性樹脂組成物。
- 支持体と、該支持体上に設けられた感光層と、を備え、
前記感光層が、請求項1〜3のいずれか一項に記載の感光性樹脂組成物を含む、感光性エレメント。 - 請求項1〜3のいずれか一項に記載の感光性樹脂組成物の硬化物を備える、半導体装置。
- 請求項1〜3のいずれか一項に記載の感光性樹脂組成物を基材上に塗布し、前記感光性樹脂組成物を乾燥して感光層を形成する工程と、
前記感光層を所定のパターンに露光し、露光後加熱処理を行う工程と、
前記加熱処理後の前記感光層を現像し、得られた樹脂パターンを加熱処理する工程と、
を含む、レジストパターンの形成方法。 - 基材上に、請求項4に記載の感光性エレメントを用いて感光層を形成する工程と、
前記感光層を所定のパターンに露光し、露光後加熱処理を行う工程と、
前記加熱処理後の前記感光層を現像し、得られた樹脂パターンを加熱処理する工程と、
を含む、レジストパターンの形成方法。
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JPH11212263A (ja) * | 1997-10-02 | 1999-08-06 | Dainippon Printing Co Ltd | 感光性樹脂組成物 |
JP2002049150A (ja) * | 2000-08-03 | 2002-02-15 | Fuji Photo Film Co Ltd | 電子線又はx線用ネガ型レジスト組成物 |
JP2010197996A (ja) * | 2009-01-30 | 2010-09-09 | Jsr Corp | 感光性絶縁樹脂組成物及びその硬化物並びに絶縁膜の製造方法 |
JP2016009120A (ja) * | 2014-06-25 | 2016-01-18 | 日立化成株式会社 | 感光性樹脂組成物、感光性エレメント、半導体装置及びレジストパターンの形成方法 |
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JPH11212263A (ja) * | 1997-10-02 | 1999-08-06 | Dainippon Printing Co Ltd | 感光性樹脂組成物 |
JP2002049150A (ja) * | 2000-08-03 | 2002-02-15 | Fuji Photo Film Co Ltd | 電子線又はx線用ネガ型レジスト組成物 |
JP2010197996A (ja) * | 2009-01-30 | 2010-09-09 | Jsr Corp | 感光性絶縁樹脂組成物及びその硬化物並びに絶縁膜の製造方法 |
JP2016009120A (ja) * | 2014-06-25 | 2016-01-18 | 日立化成株式会社 | 感光性樹脂組成物、感光性エレメント、半導体装置及びレジストパターンの形成方法 |
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