JP6600962B2 - 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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- JP6600962B2 JP6600962B2 JP2015069733A JP2015069733A JP6600962B2 JP 6600962 B2 JP6600962 B2 JP 6600962B2 JP 2015069733 A JP2015069733 A JP 2015069733A JP 2015069733 A JP2015069733 A JP 2015069733A JP 6600962 B2 JP6600962 B2 JP 6600962B2
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- phenyl
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- 239000011342 resin composition Substances 0.000 title claims description 90
- 239000004065 semiconductor Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title description 34
- -1 methylol group Chemical group 0.000 claims description 164
- 150000001875 compounds Chemical class 0.000 claims description 69
- 229920005989 resin Polymers 0.000 claims description 45
- 239000011347 resin Substances 0.000 claims description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- 238000010438 heat treatment Methods 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
- 229920003986 novolac Polymers 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000006544 oxetanylalkyl group Chemical group 0.000 claims description 11
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 52
- 239000007983 Tris buffer Substances 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 22
- 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 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 16
- 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 15
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 229910000077 silane Inorganic materials 0.000 description 13
- 239000011229 interlayer Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229910018557 Si O Inorganic materials 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 239000011256 inorganic filler Substances 0.000 description 10
- 229910003475 inorganic filler Inorganic materials 0.000 description 10
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 150000007824 aliphatic compounds Chemical class 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 125000000962 organic group Chemical group 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- 238000009413 insulation Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011241 protective layer Substances 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000000052 comparative effect Effects 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
- WZFKGRPFVONRJT-UHFFFAOYSA-N (2-methylphenyl)-[3-methyl-4-(4-phenylphenyl)sulfanylphenyl]-(4-phenylphenyl)sulfanium Chemical compound CC1=CC([S+](C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)C)=CC=C1SC(C=C1)=CC=C1C1=CC=CC=C1 WZFKGRPFVONRJT-UHFFFAOYSA-N 0.000 description 3
- SPOYZGQWNIRJQC-UHFFFAOYSA-N (3-butan-2-yloxy-4-phenylphenyl)-[3-butoxy-4-(4-phenylphenyl)sulfanylphenyl]-phenylsulfanium Chemical compound CCCCOC(C=C(C=C1)[S+](C2=CC=CC=C2)C(C=C2)=CC(OC(C)CC)=C2C2=CC=CC=C2)=C1SC(C=C1)=CC=C1C1=CC=CC=C1 SPOYZGQWNIRJQC-UHFFFAOYSA-N 0.000 description 3
- MFNBODQBPMDPPQ-UHFFFAOYSA-N (4-tert-butylphenyl)-diphenylsulfanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 MFNBODQBPMDPPQ-UHFFFAOYSA-N 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 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
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 3
- RAHAROCCOGUUMR-UHFFFAOYSA-N C(C)(=O)C1=C(C=C(C=C1)SC1=CC=C(C=C1)[S+](C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)CC)C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)CC)CC Chemical compound C(C)(=O)C1=C(C=C(C=C1)SC1=CC=C(C=C1)[S+](C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)CC)C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)CC)CC RAHAROCCOGUUMR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 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
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 150000001565 benzotriazoles Chemical class 0.000 description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 150000003536 tetrazoles Chemical group 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- WDZBYSRNRFGAJL-UHFFFAOYSA-N tris[4-(4-acetyl-3-butylphenyl)sulfanylphenyl]sulfanium Chemical compound C(C)(=O)C1=C(C=C(C=C1)SC1=CC=C(C=C1)[S+](C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)CCCC)C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)CCCC)CCCC WDZBYSRNRFGAJL-UHFFFAOYSA-N 0.000 description 3
- PJXLCOCYFLDORL-UHFFFAOYSA-N tris[4-(4-acetyl-3-methylphenyl)sulfanylphenyl]sulfanium Chemical compound C(C)(=O)C1=C(C=C(C=C1)SC1=CC=C(C=C1)[S+](C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)C)C1=CC=C(C=C1)SC1=CC(=C(C=C1)C(C)=O)C)C PJXLCOCYFLDORL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JBWMSDFCKSGJGN-UHFFFAOYSA-N (2-methoxyphenyl)-[3-methoxy-4-(4-phenylphenyl)sulfanylphenyl]-(4-phenylphenyl)sulfanium Chemical compound COC1=CC([S+](C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)OC)=CC=C1SC(C=C1)=CC=C1C1=CC=CC=C1 JBWMSDFCKSGJGN-UHFFFAOYSA-N 0.000 description 2
- KVIQXOGKIBHAQU-UHFFFAOYSA-N (2-methylphenyl)-(4-phenylphenyl)-[4-(4-phenylphenyl)sulfanylphenyl]sulfanium Chemical compound CC1=C(C=CC=C1)[S+](C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)SC1=CC=C(C=C1)C1=CC=CC=C1 KVIQXOGKIBHAQU-UHFFFAOYSA-N 0.000 description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-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
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-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
- CNZYOVKAHSTGQW-UHFFFAOYSA-N 2-methyl-4-[4-(2-phenylphenyl)phenyl]sulfanyl-1-(4-phenylphenyl)sulfanylbenzene Chemical compound CC1=C(C=CC(=C1)SC2=CC=C(C=C2)C3=CC=CC=C3C4=CC=CC=C4)SC5=CC=C(C=C5)C6=CC=CC=C6 CNZYOVKAHSTGQW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 2
- 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
- VTPXYFSCMLIIFK-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propan-1-ol Chemical compound C1OC1COCC(COCC1OC1)(CO)COCC1CO1 VTPXYFSCMLIIFK-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
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- KZZLKYUZEIFEIC-UHFFFAOYSA-O sulfanium bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound [C-](S(=O)(=O)C(F)(F)F)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[SH3+] KZZLKYUZEIFEIC-UHFFFAOYSA-O 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
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Description
すなわち、本開示は、(A)成分:フェノール性水酸基を有する樹脂と、(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から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から選択される少なくとも1種の官能基を、2つ以上有する脂肪族化合物と、(E)成分:脂肪族アミン及び含窒素複素環化合物からなる群より選ばれる少なくとも1種の化合物と、を含有する、感光性樹脂組成物を提供する。
また、本開示の感光性樹脂組成物は、(E)成分:脂肪族アミン及び含窒素複素環化合物からなる群より選ばれる少なくとも1種の化合物を含有することにより、20μmを超える厚さを有する塗膜を形成した場合であっても、解像性に優れるとともに、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る。露光量の裕度が広い感光性樹脂組成物を用いて量産品等を製造する場合、微細なレジストパターンを形成するために、露光量を細かく調節する必要がないので、量産品のスループットを向上することができる。
なお、本明細書において、「層」との語は、平面図として観察したときに、全面に形成されている形状の構造に加え、一部に形成されている形状の構造も包含される。本明細書において、「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であっても、その工程の所期の目的が達成されれば、本用語に含まれる。本明細書において、「〜」を用いて示された数値範囲は、「〜」の前後に記載される数値をそれぞれ最小値及び最大値として含む範囲を示す。本明細書において、「Si−O結合」とは、ケイ素原子と酸素原子との結合を示す。
本実施形態の感光性樹脂組成物は、(A)成分:フェノール性水酸基を有する樹脂と、(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から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から選択される少なくとも1種の官能基を、2つ以上有する脂肪族化合物と、(E)成分:脂肪族アミン及び含窒素複素環化合物からなる群より選ばれる少なくとも1種の化合物と、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、(E)成分等と称することがある。
本実施形態の感光性樹脂組成物は、フェノール性水酸基を有する樹脂を含有する。フェノール性水酸基を有する樹脂としては、特に限定されないが、アルカリ水溶液に可溶な樹脂であることが好ましく、ノボラック樹脂が特に好ましい。該ノボラック樹脂は、例えば、フェノール類とアルデヒド類とを触媒の存在下で、縮合させることにより得られる。
また、上記アルデヒド類としては、ホルムアルデヒド、パラホルムアルデヒド、アセトアルデヒド、ベンズアルデヒド等が挙げられる。
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)
カラム仕様:10.7mmφ×300mm
溶離液:テトラヒドロフラン
測定温度:40℃
流量:1.75ml/分
検出器:L−3300RI(株式会社日立製作所製)
本実施形態の感光性樹脂組成物は、光感応性酸発生剤を含有する。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。該光感応性酸発生剤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。
ムヘキサフルオロアンチモネート、(2−エトキシ)フェニル[4−(4−ビフェニリルチオ)−3−エトキシフェニル]4−ビフェニリルスルホニウムヘキサフルオロホスフェート、(2−エトキシ)フェニル[4−(4−ビフェニリルチオ)−3−エトキシフェニル]4−ビフェニリルスルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、(2−エトキシ)フェニル[4−(4−ビフェニリルチオ)−3−エトキシフェニル]4−ビフェニリルスルホニウムテトラフルオロボレート、(2−エトキシ)フェニル[4−(4−ビフェニリルチオ)−3−エトキシフェニル]4−ビフェニリルスルホニウムテトラキス(ペンタフルオロフェニル)ボレート、(2−エトキシ)フェニル[4−(4−ビフェニリルチオ)−3−エトキシフェニル]4−ビフェニリルスルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムトリフルオロメタンスルホネート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムノナフルオロブタンスルホネート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムヘプタデカフルオロオクタンスルホネート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムp−トルエンスルホネート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムヘキサフルオロアンチモネート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムヘキサフルオロホスフェート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムテトラフルオロボレート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムテトラキス(ペンタフルオロフェニル)ボレート、(2−ブトキシ)フェニル[4−(4−ビフェニリルチオ)−3−ブトキシフェニル]4−ビフェニリルスルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムトリフルオロメタンスルホネート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムノナフルオロブタンスルホネート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムヘプタデカフルオロオクタンスルホネート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムp−トルエンスルホネート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムヘキサフルオロアンチモネート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムヘキサフルオロホスフェート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムテトラフルオロボレート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムテトラキス(ペンタフルオロフェニル)ボレート、トリス[4−(4−アセチルフェニルスルファニル)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムトリフルオロメタンスルホネート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムノナフルオロブタンスルホネート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムヘプタデカフルオロオクタンスルホネート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムp−トルエンスルホネート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムヘキサフルオロアンチモネート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムヘキサフルオロホスフェート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムテトラフルオロボレート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムテトラキス(ペンタフルオロフェニル)ボレート、トリス[4−(4−アセチル−3−メチルフェニルチオ)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムトリフルオロメタンスルホネート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムノナフルオロブタンスルホネート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムヘプタデカフルオロオクタンスルホネート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムp−トルエンスルホネート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムヘキサフルオロアンチモネート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムヘキサフルオロホスフェート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムテトラフルオロボレート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムテトラキス(ペンタフルオロフェニル)ボレート、トリス[4−(4−アセチル−3−エチルフェニルチオ)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムトリフルオロメタンスルホネート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムノナフルオロブタンスルホネート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムヘプタデカフルオロオクタンスルホネート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムp−トルエンスルホネート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムヘキサフルオロアンチモネート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムヘキサフルオロホスフェート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムテトラフルオロボレート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムテトラキス(ペンタフルオロフェニル)ボレート、トリス[4−(4−アセチル−3−ブチルフェニルチオ)フェニル]スルホニウムトリス[(トリフルオロメチル)スルホニル]メタニド等のトリアリールスルホニウム塩などが挙げられる。
本実施形態の感光性樹脂組成物は、(C)成分として、芳香環、複素環及び脂環からなる群から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を含有する(ただし、(D)成分又は(E)成分は包含されない)。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る。
本実施形態の感光性樹脂組成物は、(D)成分として、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から選択される少なくとも1種の官能基を、2つ以上有する脂肪族化合物を含有する。なお、(D)成分は、異なる2種以上の官能基を1つずつ有してもよく、1種の官能基を2つ以上有してもよい。当該化合物は、上記官能基を3つ以上有する脂肪族化合物であることが好ましい。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、脂肪族アミン及び含窒素複素環化合物からなる群より選ばれる少なくとも1種の化合物を含有することにより、感光性樹脂組成物の解像性を向上させることができる。また、(E)成分を含有することで、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。ここで、脂肪族アミンとは、主骨格が脂肪族骨格であり、芳香環又は複素環を含まないアミンを意味する。含窒素複素環化合物とは、置換されていてもよい芳香族複素環又は置換されていてもよい脂環式複素環を有し、窒素をヘテロ原子とする化合物を意味し、例えば、ピペリジン系化合物、ピペリドン系化合物、ピロリジン系化合物、テトラゾール系化合物、ベンゾトリアゾール系化合物等が挙げられる。なお、(E)成分の、含窒素複素環化合物は、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を除くものとする。
本実施形態の感光性樹脂組成物は、感光性樹脂組成物の取り扱い性を向上させたり、粘度及び保存安定性を調節したりするために、(F)成分として、溶剤を更に含有することもできる。(F)成分は、有機溶剤であることが好ましい。有機溶剤の種類は、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;メチルエチルケトン、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、Si−O結合を有する化合物を含有してもよい。(G)成分としては、Si−O結合を有していれば特に限定されないが、例えば、無機フィラー及びシラン化合物のうちSi−O結合を有する化合物、並びにSi−O結合を有する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 …(14)
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質量部の範囲であってもよい。
次に、本実施形態の感光性エレメントについて説明する。
本実施形態の感光性エレメントは、支持体と、該支持体上に設けられた感光層とを備え、該感光層は上述の感光性樹脂組成物を含む。本実施形態の感光性エレメントは、該感光層上に、該感光層を被覆する保護層を更に備えていてもよい。
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及びA−2)100質量部に対し、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、脂肪族アミン及び含窒素複素環化合物からなる群より選ばれる化合物(E−1〜E−9)と、溶剤(F−1)と、Si−O結合を有する化合物(G−1)とを、下記表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:ノボラック樹脂(旭有機材工業株式会社製、商品名:TR4020G、重量平均分子量:13000)
A−2:ノボラック樹脂(旭有機材工業株式会社製、商品名:TR4080G、重量平均分子量:5000)
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:ニカラック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:N,N−ジイソプロピルエチルアミン(東京化成工業株式会社製)
E−2:トリプロピルアミン(和光純薬工業株式会社製)
E−3:トリエチルアミン(和光純薬工業株式会社製)
E−4:トリヘキシルアミン(東京化成工業株式会社製)
E−5:1,2,3−ベンゾトリアゾール(和光純薬工業株式会社製)
E−6:2−(2−ヒドロキシ−5−tert−オクチルフェニル)ベンゾトリアゾール(株式会社ADEKA製、商品名:LA−29)
E−7:1H−テトラゾール(東京化成工業株式会社製)
E−8:5−アミノ−1H−テトラゾール(東京化成工業株式会社製)
E−9:トリアミルアミン(東京化成工業株式会社製)
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インチのシリコンウエハ上に、上記感光性エレメントの保護層を剥がし、該感光性エレメントをラミネートし、支持体と感光層とシリコンウェハとをこの順に備えた積層体を得た。ラミネートは、100℃のヒートロールを用いて、0.4MPaの圧着圧力、1.0m/分のロール速度で行った。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、露光部及び未露光部の幅が1:1となるようなパターンを、2μm:2μm〜30μm:30μmまで1μm刻みで有するものを用いた。また、露光量は、150〜1650mJ/cm2の範囲で、150mJ/cm2ずつ変化させながら縮小投影露光を行った。
Claims (8)
- (A)成分:フェノール性水酸基を有する樹脂と、
(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から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:下記一般式(7)〜(10)で表される化合物からなる群より選ばれる少なくとも1種の化合物と、
(E)成分:脂肪族アミンと、を含有し、
前記(A)成分が、ノボラック樹脂、ポリヒドロキシスチレン、フェノール−キシリレングリコール縮合樹脂、クレゾール−キシリレングリコール縮合樹脂、及びフェノール−ジシクロペンタジエン縮合樹脂からなる群より選ばれる少なくとも1種の樹脂である、感光性樹脂組成物。
[一般式(7)〜(10)中、R 1 、R 5 、R 16 及びR 19 は、それぞれ独立に水素原子、メチル基、エチル基、水酸基又は一般式(11)で表される基を示し、R 21 は水酸基、グリシジルオキシ基、アクリロイルオキシ基又はメタクリロイルオキシ基を示し、R 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 17 、R 18 及びR 20 は、それぞれ水酸基、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、アクリロイルオキシ基、メタクリロイルオキシ基、一般式(12)で表される基又は一般式(13)で表される基を示し、R 22 及びR 23 はそれぞれ独立に水酸基、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、アクリロイルオキシ基又はメタクリロイルオキシ基を示し、n及びmはそれぞれ1〜10の整数である。] - 前記(E)成分が、三級アミンを含む、請求項1に記載の感光性樹脂組成物。
- 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又は2に記載の感光性樹脂組成物。
- (G)成分:Si−O結合を有する化合物をさらに含有する、請求項1〜3のいずれか一項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請求項1〜4のいずれか一項に記載の感光性樹脂組成物を用いて形成される感光層と、を備える、感光性エレメント。
- 請求項1〜4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1〜4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5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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