JP6597980B2 - ハロゲン化スルホニルアルキル基を有するシリコン含有レジスト下層膜形成組成物 - Google Patents
ハロゲン化スルホニルアルキル基を有するシリコン含有レジスト下層膜形成組成物 Download PDFInfo
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- JP6597980B2 JP6597980B2 JP2016534394A JP2016534394A JP6597980B2 JP 6597980 B2 JP6597980 B2 JP 6597980B2 JP 2016534394 A JP2016534394 A JP 2016534394A JP 2016534394 A JP2016534394 A JP 2016534394A JP 6597980 B2 JP6597980 B2 JP 6597980B2
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- 239000000203 mixture Substances 0.000 title claims description 97
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 27
- 229910052710 silicon Inorganic materials 0.000 title claims description 24
- 125000005843 halogen group Chemical group 0.000 title claims description 19
- 239000010703 silicon Substances 0.000 title description 10
- 125000004963 sulfonylalkyl group Chemical group 0.000 title 1
- -1 methacryloyl group Chemical group 0.000 claims description 320
- 229910000077 silane Inorganic materials 0.000 claims description 63
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 57
- 239000000758 substrate Substances 0.000 claims description 52
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- 229920000642 polymer Polymers 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 38
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- 230000007062 hydrolysis Effects 0.000 claims description 28
- 238000006460 hydrolysis reaction Methods 0.000 claims description 28
- 125000000962 organic group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
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- 239000003054 catalyst Substances 0.000 claims description 22
- 238000005530 etching Methods 0.000 claims description 20
- 238000001459 lithography Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 229910018540 Si C Inorganic materials 0.000 claims description 15
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- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 8
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 8
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- 238000012545 processing Methods 0.000 claims description 6
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
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- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
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- 125000005595 acetylacetonate group Chemical group 0.000 description 40
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 40
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- 239000011259 mixed solution Substances 0.000 description 22
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- 150000002367 halogens Chemical class 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 17
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- 238000003786 synthesis reaction Methods 0.000 description 16
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- 239000007983 Tris buffer Substances 0.000 description 15
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- 239000011230 binding agent Substances 0.000 description 13
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 238000010894 electron beam technology Methods 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 12
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- 239000000460 chlorine Substances 0.000 description 12
- 230000003301 hydrolyzing effect Effects 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HQIMWHPGXMPLAV-UHFFFAOYSA-N FC(S(=O)(=O)CCC[Si](OCC)(OCC)OCC)(F)F Chemical compound FC(S(=O)(=O)CCC[Si](OCC)(OCC)OCC)(F)F HQIMWHPGXMPLAV-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 8
- 0 CC1C(CC*CCCC2CC2)CCC1 Chemical compound CC1C(CC*CCCC2CC2)CCC1 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 238000006068 polycondensation reaction Methods 0.000 description 4
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- KAVUKAXLXGRUCD-UHFFFAOYSA-M sodium trifluoromethanesulfinate Chemical compound [Na+].[O-]S(=O)C(F)(F)F KAVUKAXLXGRUCD-UHFFFAOYSA-M 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
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- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
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- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 125000001174 sulfone group Chemical group 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- LTWFAYWMPMMDGT-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;titanium Chemical compound [Ti].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C LTWFAYWMPMMDGT-UHFFFAOYSA-N 0.000 description 1
- NVQCTSGVFRPZCZ-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;zirconium Chemical compound [Zr].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C NVQCTSGVFRPZCZ-UHFFFAOYSA-N 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
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
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- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
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- SMGOKIYLLQQVJE-UHFFFAOYSA-N trichloro-[methoxy(phenyl)methyl]silane Chemical compound COC([Si](Cl)(Cl)Cl)C1=CC=CC=C1 SMGOKIYLLQQVJE-UHFFFAOYSA-N 0.000 description 1
- UEUXEIHYBASMLX-UHFFFAOYSA-N trichloro-[phenyl(propan-2-yloxy)methyl]silane Chemical compound CC(C)OC([Si](Cl)(Cl)Cl)C1=CC=CC=C1 UEUXEIHYBASMLX-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
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- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- OHKFEBYBHZXHMM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CCC)OCC1CO1 OHKFEBYBHZXHMM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- NFRRMEMOPXUROM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CC)OCC1CO1 NFRRMEMOPXUROM-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- FVMMYGUCXRZVPJ-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)OCC1CO1 FVMMYGUCXRZVPJ-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- NLKPPXKQMJDBFO-UHFFFAOYSA-N triethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OCC)(OCC)OCC)CCC2OC21 NLKPPXKQMJDBFO-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-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
- PSUKBUSXHYKMLU-UHFFFAOYSA-N triethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OCC)(OCC)OCC)CCC2OC21 PSUKBUSXHYKMLU-UHFFFAOYSA-N 0.000 description 1
- GSUGNQKJVLXBHC-UHFFFAOYSA-N triethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCOCC1CO1 GSUGNQKJVLXBHC-UHFFFAOYSA-N 0.000 description 1
- CSDVDSUBFYNSMC-UHFFFAOYSA-N triethoxysilylmethyl acetate Chemical compound CCO[Si](OCC)(OCC)COC(C)=O CSDVDSUBFYNSMC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-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
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- NBNZEBUNZGWIRJ-UHFFFAOYSA-N triphenylsulfanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NBNZEBUNZGWIRJ-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
-
- 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
- G03F7/075—Silicon-containing compounds
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Description
また、半導体基板とフォトレジストとの間の下層膜として、シリコンやチタン等の金属元素を含むハードマスクとして知られる膜を使用することが行なわれている。この場合、レジストとハードマスクでは、その構成成分に大きな違いが有るため、それらのドライエッチングによって除去される速度は、ドライエッチングに使用されるガス種に大きく依存する。そして、ガス種を適切に選択することにより、フォトレジストの膜厚の大きな減少を伴うことなく、ハードマスクをドライエッチングによって除去することが可能となる。このように、近年の半導体装置の製造においては、反射防止効果を初め、さまざまな効果を達成するために、半導体基板とフォトレジストの間にレジスト下層膜が配置されるようになってきている。そして、これまでもレジスト下層膜用の組成物の検討が行なわれてきているが、その要求される特性の多様性などから、レジスト下層膜用の新たな材料の開発が望まれている。
特に本発明は、上層レジスト膜を露光しアルカリ現像液や有機溶剤で現像した時に優れたレジストパターン形状が形成でき、後のドライエッチングにより下層に矩形なレジストパターンを転写することができるレジスト下層膜を形成するためのレジスト下層膜形成組成物を提供することにある。
〔式(1)中、R1は式(2):
(式(2)中、R4は置換されていても良い炭素原子数1乃至10のアルキレン基を示し、R5はスルホニル基、又はスルホンアミド基を示し、R6はハロゲン含有有機基を示す。)で示される有機基を示し且つSi−C結合によりケイ素原子結合しているものである。R2はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基を示し且つSi−C結合によりケイ素原子と結合しているものである。R3はアルコキシ基、アシルオキシ基、又はハロゲン基を示す。aは1の整数を示し、bは0乃至2の整数を示し、a+bは1乃至3の整数を示す。〕で示される加水分解性シランを含むリソグラフィー用レジスト下層膜形成組成物、
第2観点として、上記式(2)中、R6がフッ素含有有機基を示す第1観点に記載のレジスト下層膜形成組成物、
第3観点として、上記式(2)中、R6がトリフルオロメチル基を示す第1観点に記載のレジスト下層膜形成組成物、
第4観点として、該加水分解性シランが、式(1)で示される加水分解性シランとその他の加水分解性シランとの組み合わせであり、その他の加水分解性シランが式(3):
(式(3)中、R7はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基を示し且つSi−C結合によりケイ素原子と結合しているものであり、R8はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、cは0乃至3の整数を示す。)、及び式(4):
(式(4)中、R9はアルキル基を示し且つSi−C結合によりケイ素原子と結合しているものであり、R10はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、Yはアルキレン基又はアリーレン基を示し、dは0又は1の整数を示し、eは0又は1の整数である。)からなる群より選ばれた少なくとも1種の加水分解性シランである第1観点又は第2観点に記載のレジスト下層膜形成組成物、
第5観点として、第1観点に記載の式(1)で示される加水分解性シランと第4観点に記載の式(3)で示される加水分解性シランの組み合わせからなる加水分解性シランの加水分解縮合物を下層膜形成ポリマーとして含むレジスト下層膜形成組成物、
第6観点として、更に加水分解触媒として酸を含む第1観点乃至第5観点のいずれか一つに記載のレジスト下層膜形成組成物、
第7観点として、更に水を含む第1観点乃至第6観点のいずれか一つに記載のレジスト下層膜形成組成物、
第8観点として、第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜、
第9観点として、第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジスト膜を現像しレジストパターンを得る工程、前記レジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法、及び
第10観点として、半導体基板上に有機下層膜を形成する工程、その上に第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジスト膜を現像しレジストパターンを得る工程、前記レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機下層膜により半導体基板を加工する工程を含む半導体装置の製造方法である。
従って、本発明の組成物は半導体基板上又はその上の有機下層膜等の上に塗布したとき、上層のレジスト膜を露光しアルカリ現像液や有機溶剤で現像することにより、優れたレジストパターン形状が形成でき、後のドライエッチングにより下層に矩形なレジストパターンを転写することができるレジスト下層膜を提供できる。本発明のレジスト下層膜形成組成物からなるレジスト下層膜はまた、反射防止膜としても使用でき、しかも、レジストとのインターミキシングを起こさず、レジストに比較して大きなドライエッチング速度を有する。
従って、本発明のレジスト下層膜形成組成物はArF、KrFフォトレジスト等のレジスト下層膜形成組成物、EUVレジスト等のレジスト下層膜形成組成物、EUVレジスト上層膜形成組成物、電子線レジスト等のレジスト下層膜形成組成物、電子線レジスト上層膜形成組成物、リバース材料形成組成物、等に利用することができる。
式(2)中、R4は置換されていても良い炭素原子数1乃至10のアルキレン基を示し、R5はスルホニル基、又はスルホンアミド基を示し、R6はハロゲン含有有機基を示す。
上記式(2)中のR6がフッ素含有有機基であることが好ましく、特にトリフルオロメチル基が好ましい。
全シラン中で式(1)で示されるシランは、50モル%以下、又は0.05乃至50モル%、0.1乃至30モル%、又は0.1乃至10モル%の範囲で用いることができる。
本発明のレジスト下層膜形成組成物における固形分は、例えば0.1乃至50質量%、又は0.1乃至30質量%、0.1乃至25質量%である。ここで固形分とはレジスト下層膜形成組成物の全成分から溶剤成分を除いたものである。
固形分中に占める加水分解性シラン、その加水分解物、及びその加水分解縮合物の割合は、20質量%以上であり、例えば50乃至100質量%、60乃至99質量%、70乃至99質量%である。
また環状アルキル基を用いることもでき、例えば炭素原子数1乃至10の環状アルキル基としては、シクロプロピル基、シクロブチル基、1−メチル−シクロプロピル基、2−メチル−シクロプロピル基、シクロペンチル基、1−メチル−シクロブチル基、2−メチル−シクロブチル基、3−メチル−シクロブチル基、1,2−ジメチル−シクロプロピル基、2,3−ジメチル−シクロプロピル基、1−エチル−シクロプロピル基、2−エチル−シクロプロピル基、シクロヘキシル基、1−メチル−シクロペンチル基、2−メチル−シクロペンチル基、3−メチル−シクロペンチル基、1−エチル−シクロブチル基、2−エチル−シクロブチル基、3−エチル−シクロブチル基、1,2−ジメチル−シクロブチル基、1,3−ジメチル−シクロブチル基、2,2−ジメチル−シクロブチル基、2,3−ジメチル−シクロブチル基、2,4−ジメチル−シクロブチル基、3,3−ジメチル−シクロブチル基、1−n−プロピル−シクロプロピル基、2−n−プロピル−シクロプロピル基、1−i−プロピル−シクロプロピル基、2−i−プロピル−シクロプロピル基、1,2,2−トリメチル−シクロプロピル基、1,2,3−トリメチル−シクロプロピル基、2,2,3−トリメチル−シクロプロピル基、1−エチル−2−メチル−シクロプロピル基、2−エチル−1−メチル−シクロプロピル基、2−エチル−2−メチル−シクロプロピル基及び2−エチル−3−メチル−シクロプロピル基等が挙げられる。これらの例は上記ハロゲン化アルキル基のアルキル基部分にも適用される。
また上記アリーレン基としては、上記例示のアリール基から誘導される二価の有機基を挙げることができる。
上記メタクリロイル基を有する有機基としては、メタクリロイルメチル、メタクリロイルエチル、メタクリロイルプロピル等が挙げられる。
上記アミノ基を有する有機基としては、アミノメチル、アミノエチル、アミノプロピル等が挙げられる。
上記シアノ基を有する有機基としては、シアノエチル、シアノプロピル等が挙げられる。
ハロゲン含有有機基としては、スルホン基、スルホンアミド基に結合したハロゲン含有有機基や、塩構造を形成したハロゲン含有有機基を用いることができる。
さらにハロゲン含有有機基としては、ハロゲン原子が置換したアルキル基や、ハロゲン原子が置換したアルキル基を含む有機基が挙げられる。ハロゲン原子が置換したアルキル基としては、例えばパーフルオロメチル基(即ち、トリフルオロメチル基)、パーフルオロエチル基、パーフルオロプロピル基、パーフルオロブチル基等が挙げられる。
式(3)中、R7はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基を示し且つSi−C結合によりケイ素原子と結合しているものであり、R8はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、cは0乃至3の整数を示す。
式(4)中、R9はアルキル基を示し且つSi−C結合によりケイ素原子と結合しているものであり、R10はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、Yはアルキレン基又はアリーレン基を示し、dは0又は1の整数を示し、eは0又は1の整数である。
上記アルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基、アルコキシ基、アシルオキシ基、ハロゲン基、アリーレン基は上述の例を用いることができる。
GPCの測定条件は、例えばGPC装置(商品名HLC−8220GPC、東ソー株式会社製)、GPCカラム(商品名ShodexKF803L、KF802、KF801、昭和電工製)、カラム温度は40℃、溶離液(溶出溶媒)はテトラヒドロフラン、流量(流速)は1.0ml/min、標準試料はポリスチレン(昭和電工株式会社製)を用いて行うことができる。
また、加水分解性基の1モル当たり0.001乃至10モル、好ましくは0.001乃至1モルの加水分解触媒を用いることができる。
加水分解は完全に加水分解を行うことも、部分加水分解することでも良い。即ち、加水分解縮合物中に加水分解物やモノマーが残存していても良い。
加水分解触媒としては、金属キレート化合物、有機酸、無機酸、有機塩基、無機塩基を挙げることができる。
アンモニウム塩としては、式(D−1):
(但し、mは2乃至11、nは2乃至3の整数を、R21 はアルキル基又はアリール基を、YA −は陰イオンを示す。)で示される構造を有する第4級アンモニウム塩、式(D−2):
(但し、R22、R23、R24及びR25はアルキル基又はアリール基を、Nは窒素原子を、YA −は陰イオンを示し、且つR22、R23、R24、及びR25はそれぞれC−N結合により窒素原子と結合されているものである)で示される構造を有する第4級アンモニウム塩、
式(D−3):
(但し、R26及びR27はアルキル基又はアリール基を、YA −は陰イオンを示す)で示される構造を有する第4級アンモニウム塩、
式(D−4):
(但し、R28はアルキル基又はアリール基を、YA −は陰イオンを示す)で示される構造を有する第4級アンモニウム塩、
式(D−5):
(但し、R29及びR30はアルキル基又はアリール基を、YA −は陰イオンを示す)で示される構造を有する第4級アンモニウム塩、
式(D−6):
(但し、mは2乃至11、nは2乃至3の整数を、Hは水素原子を、YA −は陰イオンを示す)で示される構造を有する第3級アンモニウム塩が挙げられる。
(但し、R31、R32、R33、及びR34はアルキル基又はアリール基を、Pはリン原子を、YA −は陰イオンを示し、且つR31、R32、R33、及びR34はそれぞれC−P結合によりリン原子と結合されているものである)で示される第4級ホスホニウム塩が挙げられる。
(但し、R35、R36、及びR37はアルキル基又はアリール基を、Sは硫黄原子を、YA −は陰イオンを示し、且つR35、R36、及びR37はそれぞれC−S結合により硫黄原子と結合されているものである)で示される第3級スルホニウム塩が挙げられる。
硬化触媒はポリオルガノシロキサン100質量部に対して、0.01乃至10質量部、または0.01乃至5質量部、または0.01乃至3質量部である。
有機ポリマー化合物としては特に制限はなく、種々の有機ポリマーを使用することができる。縮重合ポリマー及び付加重合ポリマー等を使用することができる。ポリエステル、ポリスチレン、ポリイミド、アクリルポリマー、メタクリルポリマー、ポリビニルエーテル、フェノールノボラック、ナフトールノボラック、ポリエーテル、ポリアミド、ポリカーボネート等の付加重合ポリマー及び縮重合ポリマーを使用することができる。吸光部位として機能するベンゼン環、ナフタレン環、アントラセン環、トリアジン環、キノリン環、及びキノキサリン環等の芳香環構造を有する有機ポリマーが好ましく使用される。
有機ポリマー化合物としては、重量平均分子量が、例えば1000乃至1000000であり、または3000乃至300000であり、または5000乃至200000であり、または10000乃至100000であるポリマー化合物を使用することができる。
有機ポリマー化合物は一種のみを使用することができ、または二種以上を組み合わせて使用することができる。
有機ポリマー化合物が使用される場合、その割合としては、縮合物(ポリオルガノシロキサン)100質量部に対して、1乃至200質量部、または5乃至100質量部、または10乃至50質量部、または20乃至30質量部である。
酸発生剤としては、熱酸発生剤や光酸発生剤が挙げられる。
光酸発生剤は、レジストの露光時に酸を生ずる。そのため、下層膜の酸性度の調整ができる。これは、下層膜の酸性度を上層のレジストとの酸性度に合わせるための一方法である。また、下層膜の酸性度の調整によって、上層に形成されるレジストのパターン形状の調整ができる。
光酸発生剤が使用される場合、その割合としては、縮合物(ポリオルガノシロキサン)100質量部に対して、0.01乃至15質量部、または0.1乃至10質量部、または0.5乃至1質量部である。
本発明の組成物を用いて、基板上にレジスト下層膜を塗布法により形成するか、又は基板上の有機下層膜を介してその上にレジスト下層膜を塗布法により形成し、そのレジスト下層膜上にレジスト膜(例えば、フォトレジスト、電子線レジスト)を形成する。そして、露光と現像によりレジストパターンを形成し、そのレジストパターンを用いてレジスト下層膜をドライエッチングしてパターンの転写を行い、そのパターンにより基板を加工するか、又は有機下層膜をエッチングによりパターン転写しその有機下層膜により基板の加工を行う。
本発明では基板上に有機下層膜を成膜した後、この上に本発明のレジスト下層膜を成膜し、更にその上にフォトレジストを被覆することができる。これによりフォトレジストのパターン幅が狭くなり、パターン倒れを防ぐ為にフォトレジストを薄く被覆した場合でも、適切なエッチングガスを選択することにより基板の加工が可能になる。例えば、フォトレジストに対して十分に早いエッチング速度となるフッ素系ガスをエッチングガスとして本発明のレジスト下層膜に加工が可能であり、また本発明のレジスト下層膜に対して十分に早いエッチング速度となる酸素系ガスをエッチングガスとして有機下層膜の加工が可能であり、更に有機下層膜に対して十分に早いエッチング速度となるフッ素系ガスをエッチングガスとして基板の加工を行うことができる。
現像液としては、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物の水溶液、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム、コリンなどの水酸化四級アンモニウムの水溶液、エタノールアミン、プロピルアミン、エチレンジアミンなどのアミン水溶液等のアルカリ性水溶液を例として挙げることができる。さらに、これらの現像液に界面活性剤などを加えることもできる。現像の条件としては、温度5乃至50℃、時間10乃至600秒から適宜選択される。
現像液としては、例えば、酢酸メチル、酢酸ブチル、酢酸エチル、酢酸イソプロピル、酢酸アミル、酢酸イソアミル、メトキシ酢酸エチル、エトキシ酢酸エチル、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノプロピルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノフェニルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノプロピルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノフェニルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、2−メトキシブチルアセテート、3-メトキシブチルアセテート、4−メトキシブチルアセテート、3-メチル-3-メトキシブチルアセテート、3−エチル−3−メトキシブチルアセテート、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、2−エトキシブチルアセテート、4−エトキシブチルアセテート、4−プロポキシブチルアセテート、2−メトキシペンチルアセテート、3−メトキシペンチルアセテート、4−メトキシペンチルアセテート、2−メチル−3−メトキシペンチルアセテート、3−メチル−3−メトキシペンチルアセテート、3−メチル−4−メトキシペンチルアセテート、4−メチル−4−メトキシペンチルアセテート、プロピレングリコールジアセテート、蟻酸メチル、蟻酸エチル、蟻酸ブチル、蟻酸プロピル、乳酸エチル、乳酸ブチル、乳酸プロピル、炭酸エチル、炭酸プロピル、炭酸ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸プロピル、ピルビン酸ブチル、アセト酢酸メチル、アセト酢酸エチル、プロピオン酸メチル、プロピオン酸エチル、プロピオン酸プロピル、プロピオン酸イソプロピル、2−ヒドロキシプロピオン酸メチル、2−ヒドロキシプロピオン酸エチル、メチル−3−メトキシプロピオネート、エチル−3−メトキシプロピオネート、エチル−3−エトキシプロピオネート、プロピル−3−メトキシプロピオネート等を例として挙げることができる。さらに、これらの現像液に界面活性剤などを加えることもできる。現像の条件としては、温度5乃至50℃、時間10乃至600秒から適宜選択される。
フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
500mlナスフラスコに、3−クロロプロピルトリエトキシシラン28.00g(0.116mol)、トリフルオロメタンスルフィン酸ナトリウム23.59g(0.152mol)、テトラブチルアンモニウムヨージド(TBAI)8.59g(0.023mol)、トルエン84.00g、N−メチルピロリドン(NMP)28.00gを入れ、100℃に加熱し、24時間反応させた。反応液は、トルエン、水にて分液を行った後、エバポレーターにてトルエンを除去することで、粗生成物を得た。粗生成物を、減圧蒸留することで、目的物である化合物1(トリフルオロメタンスルホニルプロピルトリエトキシシラン)を得た。
1H−NMR(500MHz、DMSO−d6):0.78ppm(m、2H)、1.16ppm(t、9H)、1.84ppm(m、2H)、3.78ppm(m、8H)
13C−NMR(500MHz、DMSO−d6):8.6ppm、15.3ppm、18.1ppm、50.6ppm、57.9ppm、119.2ppm(q)
500mlナスフラスコに、3−クロロプロピルトリエトキシシラン50.00g(0.208mol)、メタンスルフィン酸ナトリウム22.26g(0.218mol)、よう化ナトリウム6.22g(0.042mol)、N−メチルピロリドン200.00gを入れ、150℃に加熱し、7時間反応させた。反応液は、トルエン、水にて分液を行った後、エバポレーターにてトルエンを除去することで、粗生成物を得た。粗生成物を、減圧蒸留することで、目的物である化合物2(メタンスルホニルプロピルトリエトキシシラン)を得た。
1H−NMR(500MHz、DMSO−d6):0.70ppm(m、2H)、1.16ppm(t、9H)、1.74ppm(m、2H)、2.93ppm(s、3H)、3.11ppm(m、2H)、3.76ppm(m、6H)
200ml四つ口フラスコに、3−アミノプロピルトリエトキシシラン15.00g(0.068mol)、トリエチルアミン(TEA)7.20g(0.071mol)、アセトニトリル(MeCN)60gを加え、5℃にて撹拌した。トリフルオロメタンスルホニルクロリド11.42g(0.068mol)を滴下後、25℃に昇温し、3時間撹拌した。塩をろ過後、減圧蒸留することで、目的物であるトリフルオロメタンスルホンアミドプロピルトリエトキシシランを得た。
1H−NMR(500MHz、DMSO−d6):0.58ppm(t、2H)、1.15ppm(t、9H)、1.53ppm(m、2H)、3.11ppm(d、2H)、3.75(q、6H)、9.32(s、1H)
テトラエトキシシラン24.82g(70mol%)、フェニルトリメトキシシラン1.69g(5mol%)、メチルトリエトキシシラン6.07g(20mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン2.89g(5mol%)、アセトン53.19gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.35gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン25.91g(70mol%)、メチルトリエトキシシラン6.34g(20mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン3.00g(5mol%)、4−メトキシベンジルトリメトキシシラン2.15g(5mol%)、アセトン52.89gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.85gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−2)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1600であった。
テトラエトキシシラン24.32g(70mol%)、フェニルトリメトキシシラン1.65g(5mol%)、メチルトリエトキシシラン3.87g(13mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン2.82g(5mol%)、4−メトキシベンジルトリメトキシシラン0.81g(2mol%)、フェニルスルホニルプロピルトリエトキシシラン2.89g(5mol%)、アセトン53.33gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.12gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−3)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン23.42g(70mol%)、フェニルトリメトキシシラン1.59g(5mol%)、メチルトリエトキシシラン2.29g(8mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン2.71g(5mol%)、4−メトキシベンジルトリメトキシシラン0.77g(2mol%)、フェニルスルホニルプロピルトリエトキシシラン2.78g(5mol%)、2, 2, 2, 5−トリメチル−5−(3−(トリエトキシシリル)プロピル)−1,3−ジオキサン−4,6−ジオン2.91g(5mol%)、アセトン53.57gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸10.71gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−4)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1700であった。
テトラエトキシシラン23.11g(70mol%)、フェニルトリメトキシシラン1.57g(5mol%)、アセトキシメチルトリエトキシシラン2.79g(8mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン2.68g(5mol%)、4−メトキシベンジルトリメトキシシラン0.77g(2mol%)、フェニルスルホニルプロピルトリエトキシシラン2.75g(5mol%)、2, 2, 2, 5−トリメチル−5−(3−(トリエトキシシリル)プロピル)−1,3−ジオキサン−4,6−ジオン2.87g(5mol%)、アセトン53.66gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸10.57gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−5)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw2100であった。
テトラエトキシシラン23.74g(70mol%)、トリエトキシシリルプロピルジアリルイソシアヌレート3.37g(5mol%)、メチルトリエトキシシラン5.80g(20mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン2.75g(5mol%)、アセトン53.66gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸10.85gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−6)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン24.63g(70mol%)、フェニルトリメトキシシラン1.67g(5mol%)、メチルトリエトキシシラン5.72g(19mol%)、トリフルオロメタンスルホニルプロピルトリエトキシシラン2.86g(5mol%)、ベンゼンスルホンアミドプロピルトリエトキシラン0.61g(0.1mol%)、アセトン53.24gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.26gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−7)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン24.55g(70mol%)、メチルトリエトキシシラン7.60g(20mol%)、トリエトキシシリルプロピルトリフルオロメタンスルホンアミド3.01g(5mol%)、アセトン53.18gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら1mol/lの塩酸11.36gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−8)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン25.81g(70mol%)、メチルトリエトキシシラン9.47g(30mol%)、アセトン52.92gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.80gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(4−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1700であった。
テトラエトキシシラン25.21g(70mol%)、メチルトリエトキシシラン7.71g(25mol%)、メタンスルホニルプロピルトリエトキシシラン2.45g、アセトン53.08gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸11.53gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(4−2)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
テトラエトキシシラン23.22g(70mol%)、メチルトリエトキシシラン5.68g(20mol%)、トリフルオロメチルスルホニルフェノキシプロピルトリエトキシシラン6.85g、アセトン53.63gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/lの塩酸10.62gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノメチルエーテルアセテート70.00gを加え、反応副生物であるメタノール、エタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノメチルエーテルアセテート溶液を得た。プロピレングリコールモノエチルエーテルを加え、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20/80の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(4−3)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1800であった。
上記合成例1乃至8、比較合成例1乃至3から得られたケイ素含有ポリマー、酸、硬化触媒、添加剤、溶媒、水を表1に示す割合で混合し、0.1μmのフッ素樹脂製のフィルターで濾過することによって、レジスト下層膜形成用組成物の溶液をそれぞれ調製した。表1中のポリマーの添加割合はポリマー溶液の添加量ではなく、ポリマー自体の添加量を示した。
表1中でマレイン酸はMA、ベンジルトリエチルアンモニウムクロリドはBTEAC、N−(3−トリエトキシシリルプロピル)−4,5−ジヒドロイミダゾールはIMIDTEOS、トリフェニルスルホニウム硝酸塩はTPSNO3、マレイン酸モノトリフェニルスルフォニウムはTPSMA、トリフェニルスルホニウムトリフルオロ酢酸塩はTPSTFA、トリフェニルスルホニウムクロリドはTPSCl、トリフェニルスルホニウムカンファースルホン酸塩はTPSCS、トリフェニルスルホニウムトリフルオロメタンスルホン酸塩はTPSTf、ノナフルオロブタンスルホン酸トリフェニルスルホニウムはTPSNf、トリフェニルスルホニウムアダマンタンカルボキシ-1,1,2-トリフルオロブタンスルホン酸塩はTPSAdTF、ジヒドロキシフェニルフェニルスルホニウムpトルエンスルホン酸塩はDHTPPSpTS、ビスフェニルスルホンはBPS、プロピレングリコールモノメチルエーテルアセテートはPGMEA、プロピレングリコールモノエチルエーテルはPGEE、プロピレングリコールモノメチルエーテルはPGMEと略した。水は超純水を用いた。各添加量は質量部で示した。
窒素下、100mL四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9−フルオレノン(7.28g、0.040mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、1,4−ジオキサン(6.69g、関東化学(株)製)を仕込み撹拌し、100℃まで昇温し溶解させ重合を開始した。24時間後60℃まで放冷後、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とするポリマー(式(5−1)、以下PCzFLと略す)9.37gを得た。
PCzFLの1H−NMRの測定結果は以下の通りであった。
1H−NMR(400MHz,DMSO−d6):δ7.03−7.55(br,12H),δ7.61−8.10(br,4H),δ11.18(br,1H)
PCzFLのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2800、多分散度Mw/Mnは1.77であった。
得られた樹脂20gに、架橋剤としてテトラメトキシメチルグリコールウリル(三井サイテック(株)製、商品名パウダーリンク1174)3.0g、触媒としてピリジニウムパラトルエンスルホネート0.30g、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いる有機レジスト下層膜(A層)形成組成物の溶液を調製した。
実施例1乃至8、比較例1乃至3で調製したSi含有レジスト下層膜形成組成物をスピナーを用い、シリコンウェハー上にそれぞれ塗布した。ホットプレート上で200℃1分間加熱し、Si含有レジスト下層膜(膜厚0.05μm)を形成した。そして、これらのレジスト下層膜について分光エリプソメーター(J.A.Woollam社製、VUV−VASEVU−302)を用い、波長193nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数とも呼ぶ)を測定した。
ドライエッチング速度の測定に用いたエッチャー及びエッチングガスは以下のものを用いた。
ES401(日本サイエンティフィック製):CF4
RIE−10NR(サムコ製):O2
実施例1乃至8、比較例1乃至3で調製したSi含有レジスト下層膜形成組成物の溶液をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上で240℃1分間加熱し、Si含有レジスト下層膜(膜厚0.08μm(CF4ガスでのエッチング速度測定用)、0.05μm(O2ガスでのエッチング速度測定用))をそれぞれ形成した。また、同様に有機下層膜形成組成物をスピナーを用い、シリコンウェハー上に塗布して塗膜を形成(膜厚0.20μm)した。エッチングガスとしてCF4ガス又はO2ガスを使用してドライエッチング速度を測定し、実施例1乃至8、比較例1乃至3のSi含有レジスト下層膜のドライエッチング速度について比較を行った。フッ素系ガスのドライエッチレートは(nm/min)として記載した。また、酸素系ガスの速度比は、(Si含有レジスト下層膜のドライエッチング速度)/(有機下層膜のドライエッチング速度)で計算した。
上記式(5−1)を含む有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で240℃で60秒間ベークし、膜厚200nmの有機下層膜(A層)を得た。その上に、実施例1乃至8、比較例1乃至3で得られたSi含有レジスト下層膜(B層)形成組成物を塗布し、ホットプレート上で240℃で60秒間ベークし、Si含有レジスト下層膜(B層)を得た。Si含有レジスト下層膜(B層)の膜厚は30nmであった。
B層の上に市販のフォトレジスト溶液(富士フイルム(株)製、商品名FAiRS−9521NT05)をスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて1分間加熱し、膜厚85nmのフォトレジスト膜(C層)を形成した。
(株)ニコン製NSR−S307Eスキャナー(波長193nm、NA、σ:0.85、0.93/0.85)を用い、現像後にフォトレジストのライン幅及びそのライン間の幅が0.060μm、すなわち0.060μmのラインアンドスペース(L/S)=1/2のデンスラインが形成されるように設定されたマスク、また現像後にフォトレジストのライン幅及びそのライン間の幅が0.058μm、すなわち0.058μmのラインアンドスペース(L/S)=1/1のデンスラインが形成されるように設定されたマスクにそれぞれを通して露光を行った。その後、ホットプレート上100℃で60秒間ベークし、冷却後、酢酸ブチル(溶剤現像液)を用いて60秒現像し、レジスト下層膜(B層)上にネガ型のパターンを形成した。得られたフォトレジストパターンについて、大きなパターン剥がれやアンダーカット、ライン底部の太り(フッティング)が発生しないものを良好として評価した。
上記有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で215℃で60秒間ベークし、膜厚90nmの有機下層膜(A層)を得た。その上に、本発明の実施例1、6乃至8、比較例1乃至3で調製されたレジスト下層膜形成組成物溶液をスピンコートし、215℃で1分間加熱することにより、レジスト下層膜(B層)(20nm)を形成した。そのハードマスク上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をスピンコートし加熱を行い、EUVレジスト膜(C層)を形成し、EUV露光装置(Micro Exposure Tool 略称MET)を用い、NA=0.30、σ=0.36/0.93 Quadropoleの条件で露光した。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、現像及びリンス処理をし、レジストパターンを形成した。評価は、26nmのラインアンドスペースの形成可否、パターン断面観察によるパターン形状を評価した。
表3で(良好)とはフッティングからアンダーカットの間の形状であり、かつスペース部に著しい残渣がないという状態を示し、(倒れ)とはレジストパターンが剥がれ倒壊しているという好ましくない状態を示し、(ブリッジ)とはレジストパターンの上部もしくは下部同士が接触しているという好ましくない状態を示し、(レジスト塗布性×)とはレジスト製膜後に弾きが見られ製膜状態が好ましくなかった状態を示す。
Claims (8)
- シランとして加水分解性シラン、その加水分解物、その加水分解縮合物、又はそれらの組み合わせを含み、該加水分解性シランが式(1):
- 該加水分解性シランが、式(1)で示される加水分解性シランとその他の加水分解性シランとの組み合わせであり、その他の加水分解性シランが式(3):
- 請求項1に記載の式(1)で示される加水分解性シランと請求項2に記載の式(3)で示される加水分解性シランの組み合わせからなる加水分解性シランの加水分解縮合物を下層膜形成ポリマーとして含むレジスト下層膜形成組成物。
- 更に加水分解触媒として酸を含む請求項1乃至請求項3のいずれか1項に記載のレジスト下層膜形成組成物。
- 更に水を含む請求項1乃至請求項4のいずれか1項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜。
- 請求項1乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジスト膜を現像しレジストパターンを得る工程、前記レジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 半導体基板上に有機下層膜を形成する工程、その上に請求項1乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジスト膜を現像しレジストパターンを得る工程、前記レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
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