TWI793388B - 矽烷 - Google Patents
矽烷 Download PDFInfo
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- TWI793388B TWI793388B TW108146689A TW108146689A TWI793388B TW I793388 B TWI793388 B TW I793388B TW 108146689 A TW108146689 A TW 108146689A TW 108146689 A TW108146689 A TW 108146689A TW I793388 B TWI793388 B TW I793388B
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 87
- 239000000758 substrate Substances 0.000 claims abstract description 50
- 239000004065 semiconductor Substances 0.000 claims abstract description 38
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 29
- 238000001459 lithography Methods 0.000 claims abstract description 26
- 125000000962 organic group Chemical group 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 23
- 229910018540 Si C Inorganic materials 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 229910010271 silicon carbide Inorganic materials 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 238000000576 coating method Methods 0.000 claims abstract description 15
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 14
- 238000010304 firing Methods 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims abstract description 12
- -1 acryl Chemical group 0.000 claims description 256
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 238000005530 etching Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 150000004756 silanes Chemical class 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000005641 methacryl group Chemical group 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 238000000059 patterning Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 17
- 239000010408 film Substances 0.000 description 175
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000010410 layer Substances 0.000 description 52
- 229920002120 photoresistant polymer Polymers 0.000 description 49
- 229920000642 polymer Polymers 0.000 description 48
- 150000001875 compounds Chemical class 0.000 description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- 239000007789 gas Substances 0.000 description 34
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 32
- 239000002253 acid Substances 0.000 description 31
- 241000208340 Araliaceae Species 0.000 description 30
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 30
- 235000003140 Panax quinquefolius Nutrition 0.000 description 30
- 235000008434 ginseng Nutrition 0.000 description 30
- 229910052719 titanium Inorganic materials 0.000 description 30
- 239000010936 titanium Substances 0.000 description 30
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 229910052726 zirconium Inorganic materials 0.000 description 27
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 25
- 238000001312 dry etching Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 21
- 150000001450 anions Chemical class 0.000 description 19
- 150000004820 halides Chemical class 0.000 description 19
- 230000007062 hydrolysis Effects 0.000 description 17
- 238000006460 hydrolysis reaction Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 150000003863 ammonium salts Chemical class 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 229940093499 ethyl acetate Drugs 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 229920000620 organic polymer Polymers 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000010703 silicon Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 238000004090 dissolution Methods 0.000 description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- AMUZLNGQQFNPTQ-UHFFFAOYSA-J 3-oxohexanoate zirconium(4+) Chemical compound [Zr+4].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O AMUZLNGQQFNPTQ-UHFFFAOYSA-J 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
- GSCOPSVHEGTJRH-UHFFFAOYSA-J [Ti+4].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O Chemical compound [Ti+4].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O GSCOPSVHEGTJRH-UHFFFAOYSA-J 0.000 description 8
- 125000003158 alcohol group Chemical group 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229940006460 bromide ion Drugs 0.000 description 8
- 125000002843 carboxylic acid group Chemical group 0.000 description 8
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 8
- 229940006461 iodide ion Drugs 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- 238000005292 vacuum distillation Methods 0.000 description 8
- 235000012431 wafers Nutrition 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- CZYXTMFMTTWHOT-UHFFFAOYSA-N C(C)(=O)CC(C[Zr])=O Chemical compound C(C)(=O)CC(C[Zr])=O CZYXTMFMTTWHOT-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000287 crude extract Substances 0.000 description 7
- 238000010894 electron beam technology Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000005406 washing Methods 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
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229940022663 acetate Drugs 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 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
- 125000003700 epoxy group Chemical group 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 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
- 239000003921 oil Substances 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 5
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 4
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000008542 feiji Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
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Images
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
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Abstract
提供一種微影用阻劑下層膜形成組成物,其使用亦能吸收KrF光的水解性矽烷之水解縮合物,用以形成可作為硬遮罩使用之阻劑下層膜。
含有水解性矽烷、其水解物或其水解縮合物作為矽烷,該水解性矽烷含有以式(1)所示之水解性矽烷,該矽烷全體中硫原子相對於矽原子的比例為7莫耳%以上之微影用阻劑下層膜形成組成物。藉由將阻劑下層膜形成組成物塗佈於半導體基板上並燒成,以獲得阻劑下層膜。
【化1】R1 aR2 bSi(R3)4-(a+b) 式(1)〔式(1)中,R1係表示以式(2)所示之有機基,且以Si-C鍵結與矽原子鍵結者。R3係表示烷氧基、醯氧基或鹵素基。a係表示1的整數,b係表示0至2的整數,a+b係表示1至3的整數〕。
Description
本發明係關於在使用於半導體裝置製造的基板與阻劑(例如光阻劑、電子束阻劑)之間,用以形成下層膜之組成物。更詳細地說,係關於在半導體裝置製造的微影步驟中,用以形成使用於光阻下層的下層膜之微影用阻劑下層膜形成組成物。又,關於使用了該下層膜形成組成物之阻劑圖型的形成方法。
以往在半導體裝置的製造中,已透過使用了光阻之微影技術進行微細加工。前述微細加工係於矽晶圓等半導體基板上形成光阻薄膜,通過其上方之描有半導體裝置圖型的遮罩圖型來照射紫外線等之活性光以使其顯影,再透過將所得之阻劑圖型當作保護膜來對基板進行蝕刻處理,於基板表面上形成與前述圖型相對應之細微凹凸的加工法。然而,近年半導體裝置的高集成度化演進,使得所用之活性光線亦有從KrF準分子雷射(248nm)向ArF準分子雷射(193nm)短波長化的傾向,而隨之活性
光自半導體基板之反射的影響成為一大問題。
此外,作為半導體基板與光阻之間的下層膜,已使用了作為含矽及鈦等金屬元素之硬遮罩的已知膜。此時阻劑與硬遮罩之間,由於其構成成分有很大的不同,故其以乾蝕刻去除的速度與乾蝕刻中所使用之氣體種類有很大的關連。然後藉由適當地選擇氣體種類,能夠在以乾蝕刻去除硬遮罩時,不會伴隨著光阻的膜厚大幅減少。如此,近年來之半導體裝置製造中始於防止反射效果,還為了達成各種效果而在半導體基板與光阻之間配置了阻劑下層膜。然後,至此雖然亦對阻劑下層膜用之組成物進行了探討,但從其需求特性的多樣性等方面來看,阻劑下層膜用之新穎材料的開發是被期望的。
例如,已提出含有使用了具有碸構造之矽烷的聚矽氧烷之阻劑下層膜(參照專利文獻1)。
已提出含有使用了具有磺醯胺構造之矽烷的聚矽氧烷之阻劑下層膜(參照專利文獻2)。
已提出含有使用了具有碸構造及胺構造之矽烷的聚矽氧烷之阻劑下層膜(參照專利文獻3)。
已提出含有使用了具有硫鍵之矽烷的聚矽氧烷之阻劑下層膜(參照專利文獻4、專利文獻5)。
[先前技術文獻]
[專利文獻]
[專利文獻1]國際公開WO2013-022099小冊子
[專利文獻2]國際公開WO2011-033965小冊子
[專利文獻3]國際公開WO2013-191203小冊子
[專利文獻4]國際公開WO2010-140551小冊子
[專利文獻5]日本特開2008-309929
本發明之目的係提供可用於半導體裝置製造的微影用阻劑下層膜形成組成物。更詳細地說,係提供用以形成可用作硬遮罩之阻劑下層膜的微影用阻劑下層膜形成組成物。又,提供用以形成可用作反射防止膜之阻劑下層膜的微影用阻劑下層膜形成組成物。又,提供不會發生與阻劑之互混,並相較於阻劑具有較大乾蝕刻速度之微影用阻劑下層膜及用以形成該下層膜之阻劑下層膜形成組成物。
特別是本發明之目的係提供阻劑下層膜形成組成物,用以形成將上層阻劑曝光並在鹼顯影液及有機溶劑中顯影時可形成優良的阻劑圖型形狀,且藉由之後的乾蝕刻可在下層轉錄矩形之阻劑圖型的阻劑下層膜。
進而,將由阻劑下層膜形成組成物所形成之該阻劑下層膜利用作硬遮罩時,在使用KrF(248nm)之曝光波長的微影製程中,若使用作為KrF光之發色團的蒽及菲等縮環構造或萘二甲醯亞胺構造,則會因分子量大而難以將此
等成分蒸餾純化,其結果造成了在半導體製造中難以去除雜質金屬的問題。本發明之目的亦為提供既能夠吸收KrF光,並且使用了因分子量小而可容易地蒸餾純化之發色團的阻劑下層膜形成組成物。
作為本發明之第1觀點,係一種微影用阻劑下層膜形成組成物,其包含水解性矽烷、其水解物或其水解縮合物作為矽烷,該水解性矽烷含有式(1):
[化1]R1 aR2 bSi(R3)4-(a+b) 式(1)
〔式(1)中,R1表示式(2):
作為第2觀點,係如第1觀點之微影用阻劑下層膜形成組成物,其中矽烷全體中相對於矽原子之硫原子的比例為7至50莫耳%。
作為第3觀點,係如第1觀點或第2觀點之阻劑下層膜形成組成物,其中該水解性矽烷為式(1)所示之水解性矽烷與其他水解性矽烷之組合,其他之水解性矽烷為選自式(3):
[化3]R7 cSi(R8)4-c式(3)(式(3)中,R7表示烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、或氰基之有機基且為藉由Si-C鍵結與矽原子鍵結者,R8表示烷氧基、醯氧基或鹵素基,c表示0至3整數)、及式(4):
[化4]〔R9 dSi(R10)3-d〕2YR e 式4)(式(4)中,R9表示烷基且為藉由Si-C鍵結與矽原子鍵結者,R10表示烷氧基、醯氧基或鹵素基,YR表示伸烷基
或伸芳基,d表示0或1之整數,e表示0或1之整數)所成群中之至少1種的水解性矽烷。
作為第4觀點,係一種阻劑下層膜形成組成物,其含有由如第1觀點之式(1)所示之水解性矽烷與如第3觀點之式(3)所示之水解性矽烷的組合而成之水解性矽烷之水解縮合物作為下層膜形成聚合物。
作為第5觀點,係如第1觀點至請第4觀點中任1項之阻劑下層膜形成組成物,其中進一步含有酸作為水解觸媒。
作為第6觀點,係如第1觀點至第5觀點中任1項之阻劑下層膜形成組成物,其中進一步含有水。
作為第7觀點,係一種阻劑下層膜,其係將如第1觀點至第6觀點中任1項之阻劑下層膜形成組成物塗佈於半導體基板上進行燒成而得。
作為第8觀點,係一種半導體裝置之製造方法,其包含下述步驟:將如第1觀點至第6觀點中任1項之阻劑下層膜形成組成物塗佈於半導體基板進行燒成形成阻劑下層膜的步驟、於前述下層膜上塗佈阻劑組成物形成阻劑膜的步驟、將前述阻劑膜曝光的步驟、曝光後將阻劑進行顯影而得到阻劑圖型的步驟、藉由前述阻劑圖型蝕刻阻劑下層膜的步驟、及藉由圖型化之阻劑下層膜加工半導體基板的步驟。
作為第9觀點,係一種半導體裝置之製造方法,其包含下述步驟:於半導體基板上形成有機下層膜的步驟、於
其上塗佈如第1觀點至第6觀點中任1項之阻劑下層膜形成組成物進行燒成形成阻劑下層膜的步驟、於前述阻劑下層膜上塗佈阻劑組成物形成阻劑膜的步驟、將前述阻劑膜曝光的步驟、曝光後將阻劑進行顯影而得到阻劑圖型的步驟、藉由前述阻劑圖型蝕刻阻劑下層膜的步驟、藉由圖型化之阻劑下層膜蝕刻有機下層膜的步驟、及藉由圖型化之有機下層膜加工半導體基板的步驟。以及:
作為第10觀點,係一種式(1’)所示之矽烷:
[化5]R1 aR2 bSi(R3)4-(a+b) 式(1’)〔式(1’)中,R1表示式(2’):
本發明之微影用阻劑下層膜形成組成物可使用於半導體裝置的製造。
又,本發明之微影用阻劑下層膜形成組成物可作為硬遮罩使用,且另根據使用之曝光用光的波長可作為反射防止膜使用,並且該組成物與阻劑不會發生互混,與阻劑相比具有較大的乾蝕刻速度。因此,本發明之微影用阻劑下層膜形成組成物,在將上層阻劑曝光並以鹼顯影液及有機溶劑進行顯影時能夠形成優良的阻劑圖型形狀,且能夠藉由之後的乾蝕刻在下層轉錄矩形之阻劑圖型。
此外,本發明之阻劑下層膜形成組成物中所含之水解性矽烷,係因分子量低而能夠容易地蒸餾純化。因此,由於本發明之阻劑下層膜形成組成物形成了雜質金屬含量低的阻劑下層膜,故即使在使用KrF(248nm)之曝光波長的微影中亦能製造雜質少的半導體製品。
[圖1]圖1係表示化合物1之NMR譜的圖示。
[圖2]圖2係表示化合物2之NMR譜的圖示。
[圖3]圖3係表示化合物3之NMR譜的圖示。
[圖4]圖4係表示化合物4之NMR譜的圖示。
[圖5]圖5係表示化合物5之NMR譜的圖示。
[圖6]圖6係表示化合物6之NMR譜的圖示。
[圖7]圖7係表示比較化合物1之NMR譜的圖示。
本發明係含有水解性矽烷、其水解物或其解縮合物作為矽烷,且該水解性矽烷含有以式(1)所示之水解性矽烷,並該矽烷全體中硫原子相對於矽原子之比例在7莫耳%以上的微影用阻劑下層膜形成組成物。式(1)中,R1係表示以式(2)所示之有機基,且以Si-C鍵結與矽原子鍵結者。又,R2係表示烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、胺基或氰基之有機基,且以Si-C鍵結與矽原子鍵結者。又,R3係表示烷氧基、醯氧基或鹵素基。a係表示1的整數,b係表示0至2的整數,a+b係表示1至3的整數。
式(2)中,X及Y係各自表示氧原子或硫原子,但是X與Y不同時為相同原子,即在本發明中會顯示X為氧原子且Y為硫原子的情況,以及X為硫原子且Y為氧原子的情況。透過使用硫原子可形成硫醚鍵,透過使用氧原子則可形成醚鍵。
R6係表示可被取代之碳原子數1至10的烷基,R4係
表示可被取代之碳原子數1至10的伸烷基,R5係表示可被取代之碳原子數1至10的烷基。n係表示0至4之整數,R4的一部分結合於Si原子上。
全矽烷中以式(1)所示之矽烷,能在50莫耳%以下、或5至50莫耳%、7至50莫耳%、或7至40莫耳%、或7至35莫耳%、或7至30莫耳%、或7至20莫耳%、或10至50莫耳%、或10至45莫耳%、或10至40莫耳%、或10至35莫耳%、或10至30莫耳%、或7至20莫耳%的範圍內使用。
本發明之阻劑下層膜形成組成物係含有以式(1)所示之水解性矽烷,或是含有以式(1)所示之水解性矽烷和其他水解性矽烷(例如以式(3)所示之水解性矽烷)、其水解物或其水解縮合物和溶劑。並且可含有作為任意成分之酸、水、醇、硬化觸媒、酸產生劑、其他有機聚合物、吸光性化合物及界面活性劑等。
本發明之阻劑下層膜形成組成物中的固形分例如為0.1至50質量%、或0.1至30質量%、0.1至25質量%。此處所謂的固形分,係從阻劑下層膜形成組成物之全部成分中去除溶劑成分者。
固形分中所占之水解性矽烷、其水解物及其水解縮合物之比例為20質量%以上,例如50至100質量%、60至99質量%、70至99質量%。
作為上述烷基可為具有直鏈或分枝之碳原子數1至10之烷基,可舉出例如甲基、乙基、n-丙基、i-丙
基、n-丁基、i-丁基、s-丁基、t-丁基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基及1-乙基-2-甲基-n-丙基等。
此外使用環狀烷基亦可,例如可舉出作為碳原子數1至10之環狀烷基的環丙基、環丁基、1-甲基-環丙基、2-甲基-環丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-n-丙基-環丙基、2-n-丙基-環丙基、1-i-丙基-環丙基、2-i-丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基及2-乙基-3-甲基-環丙基等。此等範例亦適用於上述鹵化烷基的烷基部分。
作為上述伸烷基係可舉出來自上述烷基的伸
烷基,例如可舉出甲基者為亞甲基、乙基者為伸乙基、丙基者為伸丙基。
作為上述烯基可舉出碳原子數2至10的烯基,並可舉出乙烯基、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-n-丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-i-丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-環戊烯基、2-環戊烯基、3-環戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-n-丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-n-丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-s-丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二
甲基-3-丁烯基、1-i-丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-i-丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-n-丙基-1-丙烯基、1-n-丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-t-丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-i-丙基-1-丙烯基、1-i-丙基-2-丙烯基、1-甲基-2-環戊烯基、1-甲基-3-環戊烯基、2-甲基-1-環戊烯基、2-甲基-2-環戊烯基、2-甲基-3-環戊烯基、2-甲基-4-環戊烯基、2-甲基-5-環戊烯基、2-亞甲基-環戊基、3-甲基-1-環戊烯基、3-甲基-2-環戊烯基、3-甲基-3-環戊烯基、3-甲基-4-環戊烯基、3-甲基-5-環戊烯基、3-亞甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。
作為上述芳基可舉出碳原子數6至20的芳基,例如可舉出苯基、o-甲基苯基、m-甲基苯基、p-甲基苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-巰基苯基、o-甲氧基苯基、p-甲氧基苯基、p-胺基苯基、p-氰基苯基、α-萘基、β-萘基、o-聯苯基、m-聯苯基、p-聯苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基及9-菲基等。此等範例亦可適用於上述鹵化芳基及烷氧基芳基的芳基部分。
又,作為上述伸芳基可舉出從上述實例之芳基所衍生
的二價有機基。
作為上述具有環氧基的有機基,可舉出環氧丙氧基甲基、環氧丙氧基乙基、環氧丙氧基丙基、環氧丙氧基丁基、環氧基環己基等。
作為上述具有丙烯醯基的有機基,可舉出丙烯醯基甲基、丙烯醯基乙基、丙烯醯基丙基等。
作為具有甲基丙烯醯基的有機基,可舉出甲基丙烯醯基甲基、甲基丙烯醯基乙基、甲基丙烯醯基丙基等。
作為上述具有巰基的有機基,可舉出乙基巰基、丁基巰基、己基巰基、辛基巰基等。
作為上述具有胺基的有機基,可舉出胺基甲基、胺基乙基、胺基丙基等。
作為上述具有氰基的有機基,可舉出氰基乙基、氰基丙基等。
作為上述烷氧基,可舉出具有碳原子數1至20的直鏈、分支、環狀之烷基部分的烷氧基,例如可舉出甲氧基、乙氧基、n-丙氧基、i-丙氧基、n-丁氧基、i-丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、1-甲基-n-丁氧基、2-甲基-n-丁氧基、3-甲基-n-丁氧基、1,1-二甲基-n-丙氧基、1,2-二甲基-n-丙氧基、2,2-二甲基-n-丙氧基、1-乙基-n-丙氧基、n-己氧基、1-甲基-n-戊氧基、2-甲基-n-戊氧基、3-甲基-n-戊氧基、4-甲基-n-戊氧基、1,1-二甲基-n-丁氧基、1,2-二甲基-n-丁氧基、1,3-二甲基-n-丁氧基、2,2-二甲基-n-丁氧基、2,3-二甲基-n-丁氧基、3,3-二甲基-
n-丁氧基、1-乙基-n-丁氧基、2-乙基-n-丁氧基、1,1,2-三甲基-n-丙氧基、1,2,2-三甲基-n-丙氧基、1-乙基-1-甲基-n-丙氧基及1-乙基-2-甲基-n-丙氧基等;另作為環狀之烷氧基可舉出環丙氧基、環丁氧基、1-甲基-環丙氧基、2-甲基-環丙氧基、環戊氧基、1-甲基-環丁氧基、2-甲基-環丁氧基、3-甲基-環丁氧基、1,2-二甲基-環丙氧基、2,3-二甲基-環丙氧基、1-乙基-環丙氧基、2-乙基-環丙氧基、環己氧基、1-甲基-環戊氧基、2-甲基-環戊氧基、3-甲基-環戊氧基、1-乙基-環丁氧基、2-乙基-環丁氧基、3-乙基-環丁氧基、1,2-二甲基-環丁氧基、1,3-二甲基-環丁氧基、2,2-二甲基-環丁氧基、2,3-二甲基-環丁氧基、2,4-二甲基-環丁氧基、3,3-二甲基-環丁氧基、1-n-丙基-環丙氧基、2-n-丙基-環丙氧基、1-i-丙基-環丙氧基、2-i-丙基-環丙氧基、1,2,2-三甲基-環丙氧基、1,2,3-三甲基-環丙氧基、2,2,3-三甲基-環丙氧基、1-乙基-2-甲基-環丙氧基、2-乙基-1-甲基-環丙氧基、2-乙基-2-甲基-環丙氧基及2-乙基-3-甲基-環丙氧基等。此等範例亦適用於上述烷氧基芳基的烷氧基部分。
作為上述醯氧基,可舉出碳原子數2至20的醯氧基,例如可舉出甲基羰氧基、乙基羰氧基、n-丙基羰氧基、i-丙基羰氧基、n-丁基羰氧基、i-丁基羰氧基、s-丁基羰氧基、t-丁基羰氧基、n-戊基羰氧基、1-甲基-n-丁基羰氧基、2-甲基-n-丁基羰氧基、3-甲基-n-丁基羰氧基、1,1-二甲基-n-丙基羰氧基、1,2-二甲基-n-丙基羰氧基、
2,2-二甲基-n-丙基羰氧基、1-乙基-n-丙基羰氧基、n-己基羰氧基、1-甲基-n-戊基羰氧基、2-甲基-n-戊基羰氧基、3-甲基-n-戊基羰氧基、4-甲基-n-戊基羰氧基、1,1-二甲基-n-丁基羰氧基、1,2-二甲基-n-丁基羰氧基、1,3-二甲基-n-丁基羰氧基、2,2-二甲基-n-丁基羰氧基、2,3-二甲基-n-丁基羰氧基、3,3-二甲基-n-丁基羰氧基、1-乙基-n-丁基羰氧基、2-乙基-n-丁基羰氧基、1,1,2-三甲基-n-丙基羰氧基、1,2,2-三甲基-n-丙基羰氧基、1-乙基-1-甲基-n-丙基羰氧基、1-乙基-2-甲基-n-丙基羰氧基、苯基羰氧基及甲苯磺醯基羰氧基等。
作為上述鹵素基係可舉出氟、氯、溴、碘等,此等範例亦可適用於上述鹵化烷基及鹵化芳基的鹵素基部分。
以式(1)所示之水解性矽烷可例示如下。
在本發明中,該水解性矽烷係以式(1)所示
之水解性矽烷及其它水解性矽烷的組合,其它水解性矽烷可使用從下述式(3)及式(4)所成群中選出至少1種之水解性矽烷。
[化10]R7 cSi(R8)4-c 式(3)
式(3)中,R7係表示烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基,且以Si-C鍵結與矽原子鍵結者,R8係表示烷氧基、醯氧基或鹵素基,c係表示0至3之整數。
[化11]〔R9 dSi(R10)3-d〕2YR e 式(4)
式(4)中,R9係表示烷基,且以Si-C鍵結與矽原子鍵結者,R10係表示烷氧基、醯氧基或鹵素基,YR係表示伸烷基或伸芳基,d係表示0或1之整數,e係表示0或1之整數。
作為上述式(3)及式(4)中所定義的烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、或具有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基,以及烷氧基、醯氧基、鹵素基、伸烷基、伸芳基,係可使用上述之例。
以式(3)所示之含矽化合物,係可舉出例如
四甲氧基矽烷、四氯矽烷、四乙醯氧基矽烷、四乙氧基矽烷、四n-丙氧基矽烷、四異丙氧基矽烷、四n-丁氧基矽烷、甲基三甲氧基矽烷、甲基三氯矽烷、甲基三乙醯氧基矽烷、甲基三丙氧基矽烷、甲基三丁氧基矽烷、甲基三戊氧基矽烷、甲基三苯氧基矽烷、甲基三苄氧基矽烷、甲基三苯乙氧基矽烷、環氧丙氧基甲基三甲氧基矽烷、環氧丙氧基甲基三乙氧基矽烷、α-環氧丙氧基乙基三甲氧基矽烷、α-環氧丙氧基乙基三乙氧基矽烷、β-環氧丙氧基乙基三甲氧基矽烷、β-環氧丙氧基乙基三乙氧基矽烷、α-環氧丙氧基丙基三甲氧基矽烷、α-環氧丙氧基丙基三乙氧基矽烷、β-環氧丙氧基丙基三甲氧基矽烷、β-環氧丙氧基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、γ-環氧丙氧基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三丙氧基矽烷、γ-環氧丙氧基丙基三丁氧基矽烷、γ-環氧丙氧基丙基三苯氧基矽烷、α-環氧丙氧基丁基三甲氧基矽烷、α-環氧丙氧基丁基三乙氧基矽烷、β-環氧丙氧基丁基三乙氧基矽烷、γ-環氧丙氧基丁基三甲氧基矽烷、γ-環氧丙氧基丁基三乙氧基矽烷、δ-環氧丙氧基丁基三甲氧基矽烷、δ-環氧丙氧基丁基三乙氧基矽烷、(3,4-環氧基環己基)甲基三甲氧基矽烷、(3,4-環氧基環己基)甲基三乙氧基矽烷、β-(3,4-環氧基環己基)乙基三甲氧基矽烷、β-(3,4-環氧基環己基)乙基三乙氧基矽烷、β-(3,4-環氧基環己基)乙基三丙氧基矽烷、β-(3,4-環氧基環己基)乙基三丁氧基矽烷、β-(3,4-環氧基環己基)乙基三苯氧基矽烷、γ-
(3,4-環氧基環己基)丙基三甲氧基矽烷、γ-(3,4-環氧基環己基)丙基三乙氧基矽烷、δ-(3,4-環氧基環己基)丁基三甲氧基矽烷、δ-(3,4-環氧基環己基)丁基三乙氧基矽烷、環氧丙氧基甲基甲基二甲氧基矽烷、環氧丙氧基甲基甲基二乙氧基矽烷、α-環氧丙氧基乙基甲基二甲氧基矽烷、α-環氧丙氧基乙基甲基二乙氧基矽烷、β-環氧丙氧基乙基甲基二甲氧基矽烷、β-環氧丙氧基乙基乙基二甲氧基矽烷、α-環氧丙氧基丙基甲基二甲氧基矽烷、α-環氧丙氧基丙基甲基二乙氧基矽烷、β-環氧丙氧基丙基甲基二甲氧基矽烷、β-環氧丙氧基丙基乙基二甲氧基矽烷、γ-環氧丙氧基丙基甲基二甲氧基矽烷、γ-環氧丙氧基丙基甲基二乙氧基矽烷、γ-環氧丙氧基丙基甲基二丙氧基矽烷、γ-環氧丙氧基丙基甲基二丁氧基矽烷、γ-環氧丙氧基丙基甲基二苯氧基矽烷、γ-環氧丙氧基丙基乙基二甲氧基矽烷、γ-環氧丙氧基丙基乙基二乙氧基矽烷、γ-環氧丙氧基丙基乙烯基二甲氧基矽烷、γ-環氧丙氧基丙基乙烯基二乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三氯矽烷、乙烯基三乙醯氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三乙醯氧基矽烷、甲氧基苯基三甲氧基矽烷、甲氧基苯基三乙氧基矽烷、甲氧基苯基三乙醯氧基矽烷、甲氧基苯基三氯矽烷、甲氧基苄基三甲氧基矽烷、甲氧基苄基三乙氧基矽烷、甲氧基苄基三乙醯氧基矽烷、甲氧基苄基三氯矽烷、甲氧基苯乙基三甲氧基矽烷、甲氧基苯乙基三乙氧基矽烷、甲氧基苯乙基三乙醯氧
基矽烷、甲氧基苯乙基三氯矽烷、乙氧基苯基三甲氧基矽烷、乙氧基苯基三乙氧基矽烷、乙氧基苯基三乙醯氧基矽烷、乙氧基苯基三氯矽烷、乙氧基苄基三甲氧基矽烷、乙氧基苄基三乙氧基矽烷、乙氧基苄基三乙醯氧基矽烷、乙氧基苄基三氯矽烷、異丙氧基苯基三甲氧基矽烷、異丙氧基苯基三乙氧基矽烷、異丙氧基苯基三乙醯氧基矽烷、異丙氧基苯基三氯矽烷、異丙氧基苄基三甲氧基矽烷、異丙氧基苄基三乙氧基矽烷、異丙氧基苄基三乙醯氧基矽烷、異丙氧基苄基三氯矽烷、t-丁氧基苯基三甲氧基矽烷、t-丁氧基苯基三乙氧基矽烷、t-丁氧基苯基三乙醯氧基矽烷、t-丁氧基苯基三氯矽烷、t-丁氧基苄基三甲氧基矽烷、t-丁氧基苄基三乙氧基矽烷、t-丁氧基苄基三乙醯氧基矽烷、t-丁氧基苄基三氯矽烷、甲氧基萘基三甲氧基矽烷、甲氧基萘基三乙氧基矽烷、甲氧基萘基三乙醯氧基矽烷、甲氧基萘基三氯矽烷、乙氧基萘基三甲氧基矽烷、乙氧基萘基三乙氧基矽烷、乙氧基萘基三乙醯氧基矽烷、乙氧基萘基三氯矽烷、γ-氯丙基三甲氧基矽烷、γ-氯丙基三乙氧基矽烷、γ-氯丙基三乙醯氧基矽烷、3、3、3-三氟丙基三甲氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷、γ-巰基丙基三乙氧基矽烷、β-氰基乙基三乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、二甲基二甲氧基矽烷、苯基甲基二甲氧基矽烷、二甲基二乙氧基矽烷、苯基甲基二乙氧基矽烷、γ-氯丙基甲基二甲氧基矽烷、γ-氯丙基甲基二乙氧基矽烷、二
甲基二乙醯氧基矽烷、γ-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、γ-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、γ-巰基丙基甲基二甲氧基矽烷、γ-巰基甲基二乙氧基矽烷、甲基乙烯基二甲氧基矽烷、甲基乙烯基二乙氧基矽烷等。
又,亦可使用下列之水解性矽烷。
以式(4)所示之含矽化合物,係可舉出例如亞甲基雙(三甲氧基矽烷)、亞甲基雙(三氯矽烷)、亞甲基雙(三乙醯氧基矽烷)、伸乙基雙(三乙氧基矽烷)、伸乙基雙(三氯矽烷)、伸乙基雙(三乙醯氧基矽烷)、伸丙基雙(三乙氧基矽烷)、伸丁基雙(三甲氧基矽烷)、伸苯基雙(三甲氧基矽烷)、伸苯基雙(三乙氧基矽烷)、伸苯基雙(甲基二乙氧基矽烷)、伸苯基雙
(甲基二甲氧基矽烷)、伸萘基雙(三甲氧基矽烷)、雙(三甲氧基二矽烷)、雙(三乙氧基二矽烷)、雙(乙基二乙氧基二矽烷)、雙(甲基二甲氧基二矽烷)等。
在本發明中,作為水解性矽烷另可使用具有碸基之矽烷及具有磺醯胺基之矽烷,此等例如可以下列為例。
作為本發明中使用之水解縮合物(聚矽氧烷)的具體例子係例示如下。
上述水解性矽烷的水解縮合物(聚有機矽氧烷),係可獲得重量平均分子量1000至1000000或1000至100000的縮合物。該分子量係以GPC經聚苯乙烯換算所得之分子量。
GPC的測量條件,係例如使用GPC裝置(商品名HLC-8220GPC,東曹股份有限公司製)、GPC管柱(商品名ShodexKF803L、KF802、KF801,昭和電工製),管
柱溫度為40℃,溶離液(溶出溶劑)為四氫呋喃,流量(流速)為1.0ml/min,標準試料為聚苯乙烯(昭和電工股份有限公司製)來進行。
關於烷氧基矽烷基、醯氧基矽烷基或鹵化矽烷基之水解,係每1莫耳水解性基使用0.5至100莫耳,較佳為1至10莫耳的水。
又,每1莫耳水解性基可使用0.001至10莫耳,較佳為0.001至1莫耳的水解觸媒。
水解與縮合進行時的反應溫度通常為20至80℃。
水解係進行完全水解亦可,部分水解亦可。即,水解縮合物中殘存著水解物及單體亦可。水解縮合時可使用觸媒。作為水解觸媒,可舉出金屬螯合化合物、有機酸、無機酸、有機鹼、無機鹼。
作為水解觸媒之金屬螯合化合物,可舉出例如三乙氧基‧單(乙醯丙酮基)鈦、三-n-丙氧基‧單(乙醯丙酮基)鈦、三-i-丙氧基‧單(乙醯丙酮基)鈦、三-n-丁氧基‧單(乙醯丙酮基)鈦、三-sec-丁氧基‧單(乙醯丙酮基)鈦、三-t-丁氧基‧單(乙醯丙酮基)鈦、二乙氧基‧雙(乙醯丙酮基)鈦、二-n-丙氧基‧雙(乙醯丙酮基)鈦、二-i-丙氧基‧雙(乙醯丙酮基)鈦、二-n-丁氧基‧雙(乙醯丙酮基)鈦、二-sec-丁氧基‧雙(乙醯丙酮基)鈦、二-t-丁氧基‧雙(乙醯丙酮基)鈦、單乙氧基‧參(乙醯丙酮基)鈦、單-n-丙氧基‧參(乙醯丙
酮基)鈦、單-i-丙氧基‧參(乙醯丙酮基)鈦、單-n-丁氧基‧參(乙醯丙酮基)鈦、單-sec-丁氧基‧參(乙醯丙酮基)鈦、單-t-丁氧基‧參(乙醯丙酮基)鈦、肆(乙醯丙酮基)鈦、三乙氧基‧單(乙基乙醯乙酸)鈦、三-n-丙氧基‧單(乙基乙醯乙酸)鈦、三-i-丙氧基‧單(乙基乙醯乙酸)鈦、三-n-丁氧基‧單(乙基乙醯乙酸)鈦、三-sec-丁氧基‧單(乙基乙醯乙酸)鈦、三-t-丁氧基‧單(乙基乙醯乙酸)鈦、二乙氧基‧雙(乙基乙醯乙酸)鈦、二-n-丙氧基‧雙(乙基乙醯乙酸)鈦、二-i-丙氧基‧雙(乙基乙醯乙酸)鈦、二-n-丁氧基‧雙(乙基乙醯乙酸)鈦、二-sec-丁氧基‧雙(乙基乙醯乙酸)鈦、二-t-丁氧基‧雙(乙基乙醯乙酸)鈦、單乙氧基‧參(乙基乙醯乙酸)鈦、單-n-丙氧基‧參(乙基乙醯乙酸)鈦、單-i-丙氧基‧參(乙基乙醯乙酸)鈦、單-n-丁氧基‧參(乙基乙醯乙酸)鈦、單-sec-丁氧基‧參(乙基乙醯乙酸)鈦、單-t-丁氧基‧參(乙基乙醯乙酸)鈦、肆(乙基乙醯乙酸)鈦、單(乙醯丙酮基)參(乙基乙醯乙酸)鈦、雙(乙醯丙酮基)雙(乙基乙醯乙酸)鈦、參(乙醯丙酮基)單(乙基乙醯乙酸)鈦等之鈦螯合化合物;三乙氧基‧單(乙醯丙酮基)鋯、三-n-丙氧基‧單(乙醯丙酮基)鋯、三-i-丙氧基‧單(乙醯丙酮基)鋯、三-n-丁氧基‧單(乙醯丙酮基)鋯、三-sec-丁氧基‧單(乙醯丙酮基)鋯、三-t-丁氧基‧單(乙醯丙酮基)鋯、二乙氧基‧雙(乙醯丙酮基)鋯、二-n-丙氧基‧雙(乙醯丙酮
基)鋯、二-i-丙氧基‧雙(乙醯丙酮基)鋯、二-n-丁氧基‧雙(乙醯丙酮基)鋯、二-sec-丁氧基‧雙(乙醯丙酮基)鋯、二-t-丁氧基‧雙(乙醯丙酮基)鋯、單乙氧基‧參(乙醯丙酮基)鋯、單-n-丙氧基‧參(乙醯丙酮基)鋯、單-i-丙氧基‧參(乙醯丙酮基)鋯、單-n-丁氧基‧參(乙醯丙酮基)鋯、單-sec-丁氧基‧參(乙醯丙酮基)鋯、單-t-丁氧基‧參(乙醯丙酮基)鋯、肆(乙醯丙酮基)鋯、三乙氧基‧單(乙基乙醯乙酸)鋯、三-n-丙氧基‧單(乙基乙醯乙酸)鋯、三-i-丙氧基‧單(乙基乙醯乙酸)鋯、三-n-丁氧基‧單(乙基乙醯乙酸)鋯、三-sec-丁氧基‧單(乙基乙醯乙酸)鋯、三-t-丁氧基‧單(乙基乙醯乙酸)鋯、二乙氧基‧雙(乙基乙醯乙酸)鋯、二-n-丙氧基‧雙(乙基乙醯乙酸)鋯、二-i-丙氧基‧雙(乙基乙醯乙酸)鋯、二-n-丁氧基‧雙(乙基乙醯乙酸)鋯、二-sec-丁氧基‧雙(乙基乙醯乙酸)鋯、二-t-丁氧基‧雙(乙基乙醯乙酸)鋯、單乙氧基‧參(乙基乙醯乙酸)鋯、單-n-丙氧基‧參(乙基乙醯乙酸)鋯、單-i-丙氧基‧參(乙基乙醯乙酸)鋯、單-n-丁氧基‧參(乙基乙醯乙酸)鋯、單-sec-丁氧基‧參(乙基乙醯乙酸)鋯、單-t-丁氧基‧參(乙基乙醯乙酸)鋯、肆(乙基乙醯乙酸)鋯、單(乙醯丙酮基)參(乙基乙醯乙酸)鋯、雙(乙醯丙酮基)雙(乙基乙醯乙酸)鋯、參(乙醯丙酮基)單(乙基乙醯乙酸)鋯等之鋯螯合化合物;參(乙醯丙酮基)鋁、參(乙基乙醯乙酸)鋁等之鋁螯合化
合物等。
作為水解觸媒之有機酸,可舉出例如乙酸、丙酸、丁酸、戊酸、已酸、庚酸、辛酸、壬酸、癸酸、草酸、馬來酸、甲基丙二酸、己二酸、癸二酸、没食子酸、酪酸、苯六甲酸、花生油酸、2-乙基已烷酸、油酸、硬脂酸、亞麻油酸、次亞麻油酸、水楊酸、苯甲酸、p-胺基苯甲酸、p-甲苯磺酸、苯磺酸、一氯乙酸、二氯乙酸、三氯乙酸、三氟乙酸、甲酸、丙二酸、磺酸、酞酸、富馬酸、檸檬酸、酒石酸等。
作為水解觸媒之無機酸,可舉出例如鹽酸、硝酸、硫酸、氫氟酸、磷酸等。
作為水解觸媒之有機鹼,可舉出例如吡啶、吡咯、哌嗪、吡咯啶、哌啶、甲吡啶、三甲基胺、三乙基胺、單乙醇胺、二乙醇胺、二甲基單乙醇胺、單甲基二乙醇胺、三乙醇胺、二吖雙環辛烷、二吖雙環壬烷、二吖雙環十一烯、四甲基氫氧化銨等。無機鹼可舉出例如氨、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等。此等觸媒中,較佳為金屬螯合化合物、有機酸、無機酸,此等亦可同時使用1種或2種以上。
作為用於水解的有機溶劑,可舉出例如n-戊烷、i-戊烷、n-已烷、i-已烷、n-庚烷、i-庚烷、2,2,4-三甲基戊烷、n-辛烷、i-辛烷、環己烷、甲基環己烷等之脂肪族烴系溶劑;苯、甲苯、二甲苯、乙基苯、三甲基苯、甲基乙基苯、n-丙基苯、i-丙基苯、二乙基苯、i-丁基
苯、三乙基苯、二-i-丙基苯、n-戊基萘、三甲基苯等之芳香族烴系溶劑;甲醇、乙醇、n-丙醇、i-丙醇、n-丁醇、i-丁醇、sec-丁醇、t-丁醇、n-戊醇、i-戊醇、2-甲基丁醇、sec-戊醇、t-戊醇、3-甲氧基丁醇、n-己醇、2-甲基戊醇、sec-己醇、2-乙基丁醇、sec-庚醇、庚醇-3、n-辛醇、2-乙基己醇、sec-辛醇、n-壬基醇、2,6-二甲基庚醇-4、n-癸醇、sec-十一醇、三甲基壬醇、sec-四癸醇、sec-十七醇、酚、環己醇、甲基環己醇、3,3,5-三甲基環己醇、苯甲醇、苯基甲基甲醇、二丙酮醇、甲酚等之單醇系溶劑;乙二醇、丙二醇、1,3-伸丁基乙二醇、戊二醇-2,4、2-甲基戊二醇-2,4、已二醇-2,5、庚二醇-2,4、2-乙基已二醇-1,3、二乙二醇、二丙二醇、三乙二醇、三丙二醇、甘油等之多元醇系溶劑;丙酮、甲基乙基酮、甲基-n-丙基酮、甲基-n-丁基酮、二乙基酮、甲基-i-丁基酮、甲基-n-戊基酮、乙基-n-丁基酮、甲基-n-己基酮、二-i-丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊二酮、丙酮基丙酮、二丙酮醇、苯乙酮、葑酮等之酮系溶劑;乙醚、i-丙醚、n-丁醚、n-己醚、2-乙基己醚、環氧乙烷、1,2-環氧丙烷、二氧戊環、4-甲基二氧戊環、二噁烷、二甲基二噁烷、乙二醇單甲醚、乙二醇單乙醚、乙二醇二乙醚、乙二醇單-n-丁醚、乙二醇單-n-己醚、乙二醇單苯醚、乙二醇單-2-乙基丁醚、乙二醇二丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇二乙醚、二乙二醇單-n-丁醚、二乙二醇二-n-丁醚、二乙二醇單-n-己醚、乙氧基三乙二
醇、四乙二醇二-n-丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚、丙二醇單甲醚乙酸酯、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單丙醚、二丙二醇單丁醚、三丙二醇單甲醚、四氫呋喃、2-甲基四氫呋喃等之醚系溶劑;二乙基碳酸酯、乙酸甲酯、乙酸乙酯、γ-丁內酯、γ-戊內酯、乙酸n-丙酯、乙酸i-丙酯、乙酸n-丁酯、乙酸i-丁酯、乙酸sec-丁酯、乙酸n-戊酯、乙酸sec-戊酯、乙酸3-甲氧基丁酯、乙酸甲基戊酯、乙酸2-乙基丁酯、乙酸2-乙基己酯、乙酸苄酯、乙酸環己酯、乙酸甲基環己酯、乙酸n-壬酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙酸乙二醇單甲醚、乙酸乙二醇單乙醚、乙酸二乙二醇單甲醚、乙酸二乙二醇單乙醚、乙酸二乙二醇單-n-丁醚、乙酸丙二醇單甲醚、乙酸丙二醇單乙醚、乙酸丙二醇單丙醚、乙酸丙二醇單丁醚、乙酸二丙二醇單甲醚、乙酸二丙二醇單乙醚、二乙酸乙二醇、乙酸甲氧基三乙二醇、丙酸乙酯、丙酸n-丁酯、丙酸i-戊酯、草酸二乙酯、草酸二-n-丁酯、乳酸甲酯、乳酸乙酯、乳酸n-丁酯、乳酸n-戊酯、丙二酸二乙酯、酞酸二甲酯、酞酸二乙酯等之酯系溶劑;N-甲基甲醯胺、N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、乙醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基丙醯胺、N-甲基吡咯啶酮(NMP)等之含氮系溶劑;硫化二甲酯、硫化二乙酯、噻吩、四氫化噻吩、二甲基亞碸、環丁碸、1,3-丙烷磺內酯等之含硫系溶劑等。此等溶劑可以1種或2種以上的組合使用。
特別是丙酮、甲基乙基酮、甲基-n-丙基酮、甲基-n-丁基酮、二乙基酮、甲基-i-丁基酮、甲基-n-戊基酮、乙基-n-丁基酮、甲基-n-己基酮、二-i-丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊二酮、丙酮基丙酮、二丙酮醇、苯乙酮、對酮等之酮系溶劑,在溶液的保存安定性方面為佳。
又,可添加雙酚S或雙酚S衍生物作為添加劑。雙酚S或雙酚S衍生物相對於100質量份之聚有機矽氧烷,為0.01至20質量份、0.01至10質量份或0.01至5質量份。
較佳之雙酚S或雙酚S衍生物係例示如下。
本發明之阻劑下層膜形成組成物係可含有硬化觸媒。硬化觸媒係在使含有由水解縮合物而成之聚有機矽氧烷的塗佈膜進行加熱硬化時充當硬化觸媒。
作為硬化觸媒可使用銨鹽、膦類、鏻鹽、鋶鹽。
作為銨鹽,可舉出具有以式(D-1)所示之構造的第4級銨鹽:
具有以式(D-2)所示之構造的第4級銨鹽:
[化22]R22R23R24R25N+YA - 式(D-2)(惟,R22、R23、R24及R25係表示烷基或芳基,N表示氮原子,YA -表示陰離子,且R22、R23、R24及R25係分別以C-N鍵結與氮原子鍵結者)、
具有以式(D-3)所示之構造的第4級銨鹽:
具有以式(D-4)所示之構造的第4級銨鹽:
具有以式(D-5)所示之構造的第4級銨鹽:
具有以式(D-6)所示之構造的第3級銨鹽:
又,作為鏻鹽可舉出具有以式(D-7)所示之構造的第4級鏻鹽:
[化27]R31R32R33R34P+YA - 式(D-7)(惟,R31、R32、R33及R34係表示烷基或芳基,P表示磷原子,YA -表示陰離子,且R31、R32、R33及R34係分別以C-P鍵結與磷原子鍵結者)。
又,作為鋶鹽可舉出具有以式(D-8)所示之構造的第3級鋶鹽:
[化28]R35R36R37S+YA - 式(D-8)(惟,R35、R36及R37係表示烷基或芳基,S表示硫原子,YA -表示陰離子,且R35、R36及R37係分別以C-S鍵結與硫原子鍵結者)。
上述的式(D-1)所示之化合物係自胺所衍生之第4級銨鹽,m係表示2至11、n1表示2至3之整數。該第4級銨鹽之R21係表示碳原子數1至18,較佳為2至10的烷基或芳基,例如可舉出乙基、丙基、丁基等之直鏈烷基,或苄基、環己基、環己基甲基、二環戊二烯基等。此外陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。
上述的以式(D-2)所示之化合物係以R22R23R24R25N+YA -所示之第4級銨鹽。該第4級銨鹽之R22、R23、R24及R25係碳原子數1至18的烷基或芳基,
或以Si-C鍵結與矽原子鍵結之矽烷化合物。
陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。該第4級銨鹽可透過市售品取得,例如例示有四甲基銨乙酸酯、四丁基銨乙酸酯、氯化三乙基苄基銨、溴化三乙基苄基銨、氯化三辛基甲基銨、氯化三丁基苄基銨、氯化三甲基苄基銨等。
上述的以式(D-3)所示之化合物係自1-取代咪唑所衍生之第4級銨鹽,R26及R27係碳原子數1至18的烷基或芳基,且R26及R27的碳原子數總和在7以上者為佳,例如R26可例示甲基、乙基、丙基、苯基、苄基,R27為苄基、辛基、十八烷基。陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。該化合物雖可透過市售品取得,但例如可讓1-甲基咪唑、1-苄基咪唑等之咪唑系化合物與溴化苄基、溴化甲基等之鹵化烷基及鹵化芳基進行反應來製造。
上述的以式(D-4)所示之化合物係自吡啶所衍生之第4級銨鹽,R28係碳原子數1至18,較佳為碳原子數4至18的烷基或芳基,例如可例示丁基、辛基、苄基、月桂基。陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。該化合物雖可透過市售品取得,但例如可讓吡啶與氯化月桂基、氯化苄基、溴化
苄基、溴化甲基、溴化辛基等之鹵化烷基或鹵化芳基進行反應來製造。該化合物例如可例示氯化N-月桂基吡啶鎓、溴化N-苄基吡啶鎓等。
上述的以式(D-5)所示之化合物係自以甲吡啶等為代表之取代吡啶所衍生的第4級銨鹽,R29係碳原子數1至18、較佳為4至18之烷基或芳基,例如可例示甲基、辛基、月桂基、苄基等。R30係碳原子數1至18之烷基或芳基,例如在自甲吡啶所衍生之第4級銨的情形下,R30係甲基。陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。該化合物雖可透過市售品取得,但例如可讓甲吡啶等之取代吡啶與溴化甲基、溴化辛基、氯化月桂基、氯化苄基、溴化苄基等之鹵化烷基或鹵化芳基進行反應來製造。該化合物例如可例示N-苄基甲基吡啶氯化物、N-苄基甲基吡啶溴化物、N-月桂基甲基吡啶氯化物等。
上述的以式(D-6)所示之化合物係自胺所衍生的第3級銨鹽,m係表示2至11、n1係2至3之整數。此外陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。可由胺與羧酸或酚等弱酸的反應來製造。作為羧酸可舉出甲酸及乙酸,在使用甲酸時陰離子(YA -)為(HCOO-),在使用乙酸時陰離子(YA -)則為(CH3COO-),此外在使用酚時陰離子(YA -)為(C6H5O-)。
上述的以式(D-7)所示之化合物係具有R31R32R33R34P+YA -構造的第4級鏻鹽。R31、R32、R33及R34係碳原子數1至18之烷基、或芳基或以Si-C鍵結與矽原子鍵結之矽烷化合物,但較佳為R31至R34之4個取代基中有3個為苯基或被取代之苯基,例如可例示苯基及甲苯基,另外剩餘的1個為碳原子數1至18之烷基、芳基或以Si-C鍵結與矽原子鍵結之矽烷化合物。此外陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)等之酸基。該化合物可透過市售品取得,例如可舉出鹵化四n-丁基鏻、鹵化四n-丙基鏻等之鹵化四烷基鏻,鹵化三乙基苄基鏻等之鹵化三烷基苄基鏻,鹵化三苯基甲基鏻、鹵化三苯基乙基鏻等之鹵化三苯基單烷基鏻,鹵化三苯基苄基鏻、鹵化四苯基鏻、鹵化三甲苯基單芳基鏻,或者鹵化三甲苯基單烷基鏻(鹵素原子係氯原子或溴原子)。特別是以鹵化三苯基甲基鏻、鹵化三苯基乙基鏻等之鹵化三苯基單烷基鏻,鹵化三苯基苄基鏻等之鹵化三苯基單芳基鏻,鹵化三甲苯基單苯基鏻等之鹵化三甲苯基單芳基鏻,以及鹵化三甲苯基單甲基鏻等之鹵化三甲苯基單烷基鏻(鹵素原子係氯原子或溴原子)為佳。
又,作為膦類係可舉出甲基膦、乙基膦、丙基膦、異丙基膦、異丁基膦、苯基膦等之一級膦,二甲基膦、二乙基膦、二異丙基膦、二異戊基膦、二苯基膦等之二級膦,三甲基膦、三乙基膦、三苯基膦、甲基二苯基
膦、二甲基苯基膦等之三級膦。
上述的以式(D-8)所示之化合物係具有R35R36R37S+YA -之第3級鋶鹽。R35、R36及R37係碳原子數1至18之烷基、或芳基或以Si-C鍵結與矽原子鍵結之矽烷化合物,但較佳為R35至R37之4個取代基中有3個為苯基或被取代之苯基,例如可例示苯基及甲苯基,另外剩餘的1個為碳原子數1至18之烷基或芳基。此外陰離子(YA -)係可舉出氯離子(Cl-)、溴離子(Br-)、碘離子(I-)等之鹵素離子,或羧酸基(-COO-)、磺酸根基(-SO3 -)、醇基(-O-)、馬來酸陰離子、硝酸陰離子等之酸基。
該化合物可透過市售品取得,例如鹵化三n-丁基鋶、鹵化三n-丙基鋶等之鹵化四烷基鋶、鹵化二乙基苄基鋶等之鹵化三烷基苄基鋶、鹵化二苯基甲基鋶、鹵化二苯基乙基鋶等之鹵化二苯基單烷基鋶、鹵化三苯基鋶(鹵素原子係氯原子或溴原子)、羧酸基三n-丁基鋶、羧酸基三n-丙基鋶等之羧酸基四烷基鋶、羧酸基二乙基苄基鋶等之羧酸基三烷基苄基鋶、羧酸基二苯基甲基鋶、羧酸基二苯基乙基鋶等之羧酸基二苯基單烷基鋶、羧酸基三苯基鋶。又以鹵化三苯基鋶、羧酸基三苯基鋶最為適用。
又,本發明中可添加含氮矽烷化合物作為硬化觸媒。作為含氮矽烷化合物係可舉出N-(3-三乙氧基矽基丙基)-4,5-二氫咪唑等之含咪唑環矽烷化合物。
硬化觸媒相對於100質量份之聚有機矽氧烷,為0.01至10質量份、0.01至5質量份或0.01至3質量份。
將水解性矽烷在溶劑中使用觸媒進行水解並縮合,所得之水解縮合物(聚合物)可透過減壓蒸餾等同時去除副生成物之醇、使用之水解觸媒及水。又,可藉由中和或離子交換去除用於水解之酸及鹼觸媒。並且在本發明之微影用阻劑下層膜形成組成物中,為了使含有該水解縮合物之阻劑下層膜形成組成物安定化,可添加有機酸、水、醇或其組合。
作為上述有機酸,可舉出例如草酸、丙二酸、甲基丙二酸、琥珀酸、馬來酸、蘋果酸、酒石酸、酞酸、檸檬酸、戊二酸、檸檬酸、乳酸、水楊酸等。其中又以草酸、馬來酸等為佳。加入之有機酸相對於100質量份之縮合物(聚有機矽氧烷)為0.1至5.0質量份。此外加入之水可使用純水、超純水、離子交換水等,且該添加量相對於100質量份之阻劑下層膜形成組成物可為1至20質量份。
此外作為加入之醇,較佳為易於藉由塗佈後之加熱使其飛散者,可舉出例如甲醇、乙醇、丙醇、異丙醇、丁醇等。加入之醇相對於100質量份之阻劑下層膜形成組成物可為1至20質量份。
本發明之微影用下層膜形成組成物除了上述成分之外,如有必要可含有有機聚合物化合物、光酸產生劑及界面活性劑等。
透過使用有機聚合物化合物,可調整自本發明之微影用下層膜形成組成物所形成之阻劑下層膜的乾蝕
刻速度(每單位時間之膜厚減少量)、衰減係數及折射率等。
作為有機聚合物化合物並無特別限制,可使用各種的有機聚合物,並可使用縮聚合聚合物及加成聚合聚合物等。可使用聚酯、聚苯乙烯、聚醯亞胺、丙烯酸聚合物、甲基丙烯酸聚合物、聚乙烯基醚、酚酚醛清漆、萘酚酚醛清漆、聚醚、聚醯胺、聚碳酸酯等之加成聚合聚合物及縮聚合聚合物。較佳採用具有用作吸光部位功能之苯環、萘環、蒽環、三嗪環、喹啉環及喹噁啉環等芳香環構造的有機聚合物。
作為此類有機聚合物化合物,例如可舉出苄基丙烯酸酯、苄基丙烯酸甲酯、苯基丙烯酸酯、萘基丙烯酸酯、蒽基丙烯酸甲酯、蒽基甲基丙烯酸甲酯、苯乙烯、羥基苯乙烯、苄基乙烯基醚及N-苯基順丁烯二醯亞胺等之含有加成聚合性單體以作為其構造單位的加成聚合聚合物,或酚酚醛清漆及萘酚酚醛清漆等之縮聚合聚合物。
將加成聚合聚合物使用作為有機聚合物化合物時,該聚合物化合物無論是單聚物或共聚物均可。加成聚合聚合物的製造中使用加成聚合性單體,作為此類加成聚合性單體可舉出丙烯酸、甲基丙烯酸、丙烯酸酯化合物、甲基丙烯酸酯化合物、丙烯醯胺化合物、甲基丙烯醯胺化合物、乙烯基化合物、苯乙烯化合物、順丁烯二醯亞胺化合物、馬來酸酐、丙烯腈等。
作為丙烯酸酯化合物,可舉出丙烯酸甲酯、
丙烯酸乙酯、丙烯酸N-己酯、丙烯酸異丙酯、丙烯酸環己酯、丙烯酸苄酯、丙烯酸苯酯、蒽基甲基丙烯酸酯、2-羥基乙基丙烯酸酯、3-氯基-2-羥基丙基丙烯酸酯、2-羥基丙基丙烯酸酯、2,2,2-三氟乙基丙烯酸酯、2,2,2-三氯乙基丙烯酸酯、2-溴乙基丙烯酸酯、4-羥基丁基丙烯酸酯、2-甲氧基乙基丙烯酸酯、四氫糠基丙烯酸酯、2-甲基-2-金剛烷基丙烯酸酯、5-丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-6-內酯、3-丙烯醯氧基丙基三乙氧基矽烷及丙烯酸環氧丙酯等。
作為甲基丙烯酸酯化合物,可舉出甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸N-己酯、甲基丙烯酸異丙酯、甲基丙烯酸環己酯、甲基丙烯酸苄酯、甲基丙烯酸苯酯、蒽基甲基甲基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、2-羥基丙基甲基丙烯酸酯、2,2,2-三氟乙基甲基丙烯酸酯、2,2,2-三氯乙基甲基丙烯酸酯、2-溴乙基甲基丙烯酸酯、4-羥基丁基甲基丙烯酸酯、2-甲氧基乙基甲基丙烯酸酯、四氫糠基甲基丙烯酸酯、2-甲基-2-金剛烷基甲基丙烯酸酯、5-甲基丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-6-內酯、3-甲基丙烯醯氧基丙基三乙氧基矽烷、環氧丙基甲基丙烯酸酯、2-苯基乙基甲基丙烯酸酯、羥基苯基甲基丙烯酸酯及溴苯基甲基丙烯酸酯等。
作為丙烯醯胺化合物,可舉出丙烯醯胺、N-甲基丙烯醯胺、N-乙基丙烯醯胺、N-苄基丙烯醯胺、N-苯基丙烯醯胺、N,N-二甲基丙烯醯胺及N-蒽基丙烯醯胺
等。
作為甲基丙烯醯胺化合物,可舉出甲基丙烯醯胺、N-甲基甲基丙烯醯胺、N-乙基甲基丙烯醯胺、N-苄基甲基丙烯醯胺、N-苯基甲基丙烯醯胺、N,N-二甲基甲基丙烯醯胺及N-蒽基丙烯醯胺等。
作為乙烯基化合物,可舉出乙烯醇、2-羥基乙基乙烯醚、甲基乙烯醚、乙基乙烯醚、苄基乙烯醚、乙烯基乙酸、乙烯基三甲氧基矽烷、2-氯乙基乙烯醚、2-甲氧基乙基乙烯醚、乙烯萘及乙烯蒽等。
作為苯乙烯化合物,可舉出苯乙烯、羥基苯乙烯、氯苯乙烯、溴苯乙烯、甲氧基苯乙烯、氰基苯乙烯及乙醯基苯乙烯等。
作為順丁烯二醯亞胺化合物,可舉出順丁烯二醯亞胺、N-甲基順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-環己基順丁烯二醯亞胺、N-苄基順丁烯二醯亞胺及N-羥基乙基順丁烯二醯亞胺等。
將縮聚合聚合物使用作為聚合物時,作為此類聚合物例如可舉出二醇化合物與二羧酸化合物之縮聚合聚合物。作為二醇化合物係可舉出二乙二醇、六亞甲二醇、丁二醇等。作為二羧酸化合物係可舉出琥珀酸、己二酸、對苯二甲酸、馬來酸酐等。又,例如可舉出聚均苯四甲醯亞胺、聚(對苯二甲酸對苯二胺)、聚對苯二甲酸丁二醇酯、聚對苯二甲酸乙二醇酯等之聚酯、聚醯胺、聚醯亞胺
當有機聚合物化合中含有羥基時,此羥基係可與聚有機矽氧烷形成交聯反應。作為有機聚合物化合物,係可使用例如重量平均分子量為1000至1000000,或3000至300000,或5000至200000,或10000至100000之聚合物化合物。
有機聚合物化合物係可只使用一種或兩種以上的組合。
在使用有機聚合物化合物時,作為該比例,相對於100質量份之縮合物(聚有機矽氧烷)係1至200質量份,或5至100質量份,或10至50質量份,或20至30質量份。
在本發明之阻劑下層膜形成組成物中係可含有酸產生劑。
酸產生劑係可舉出熱酸產生劑或光酸產生劑。
光酸產生劑係於阻劑曝光時產生酸,因此可調整下層膜之酸性度,此為使下層膜之酸性度與上層阻劑之酸性度相合的一種方法。又,藉由下層膜酸性度的調整,可調整在上層所形成之阻劑的圖型形狀。
作為本發明之阻劑下層膜形成組成物中所含之光酸產生劑,可舉出鎓鹽化合物、碸醯亞胺化合物及二磺醯基重氮甲烷化合物等。
作為鎓鹽化合物係可舉出二苯基碘鎓六氟磷酸鹽、二苯基碘鎓三氟甲基磺酸鹽、二苯基碘鎓九氟N-丁烷磺酸鹽、二苯基碘鎓全氟N-辛烷磺酸鹽、二苯基碘
鎓樟腦磺酸鹽、雙(4-tert-丁基苯基)碘鎓樟腦磺酸鹽及雙(4-tert-丁基苯基)碘鎓三氟甲基磺酸鹽等之碘鎓鹽化合物,及三苯基鋶六氟銻酸鹽、三苯基鋶九氟N-丁烷磺酸鹽、三苯基鋶樟腦磺酸鹽及三苯基鋶三氟甲基磺酸鹽等之鋶鹽化合物等。
作為碸醯亞胺化合物,例如可舉出N-(三氟甲基磺醯基氧基)琥珀醯亞胺、N-(九氟N-丁烷磺醯基氧基)琥珀醯亞胺、N-(樟腦磺醯基氧基)琥珀醯亞胺及N-(三氟甲基磺醯基氧基)萘二甲醯亞胺等。
作為二磺醯基重氮甲烷化合物,例如可舉出雙(三氟甲基磺醯基)重氮甲烷、雙(環己基磺醯基)重氮甲烷、雙(苯基磺醯基)重氮甲烷、雙(p-甲苯磺醯基)重氮甲烷、雙(2,4-二甲基苯磺醯基)重氮甲烷及甲基磺醯基-p-甲苯磺醯基重氮甲烷等。
光產酸劑係可只使用一種或兩種以上的組合。
在使用光產酸劑時,作為該比例,相對於100質量份之縮合物(聚有機矽氧烷)係0.01至5質量份,或0.1至3質量份,或0.5至1質量份。
界面活性劑在將本發明之微影用阻劑下層膜形成組成物塗佈於基板上時,可有效地抑制針孔及條紋等的產生。
作為本發明之阻劑下層膜形成組成物中所含之界面活性劑,例如可舉出聚氧乙烯月桂基醚、聚氧乙烯硬脂基
醚、聚氧乙烯鯨蠟醚、聚氧乙烯油基醚等之聚氧乙烯烷基醚類、聚氧乙烯辛基苯酚醚、聚氧乙烯壬基苯酚醚等之聚氧乙烯烷基烯丙基醚類、聚氧乙烯‧聚氧基伸丙基嵌段共聚物類、去水山梨醇單月桂酸酯、去水山梨醇單棕櫚酸酯、去水山梨醇單硬脂酸酯、去水山梨醇單油酸酯、去水山梨醇三油酸酯、去水山梨醇三硬脂酸酯等之去水山梨醇脂肪酸酯類、聚氧乙烯去水山梨醇單月桂酸酯、聚氧乙烯去水山梨醇單棕櫚酸酯、聚氧乙烯去水山梨醇單硬脂酸酯、聚氧乙烯去水山梨醇三油酸酯、聚氧乙烯去水山梨醇三硬脂酸酯等之聚氧乙烯去水山梨醇脂肪酸酯類等之非離子系界面活性劑,商品名EFTOP EF301、EF303、EF352((股)Tohchem Products製)、商品名MEGAFACF171、F173、R-08、R-30、R-30N、R-40LM(DIC(股)製)、FLUORAD FC430、FC431(住友3M(股)製)、商品名Asahiguard AG710,SURFLON S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製)等之氟系界面活性劑,以及有機矽氧烷Polymer-KP341(信越化學工業(股)製)等。此等界面活性劑可單獨使用,亦可兩種以上組合使用。在使用界面活性劑時,作為該比例,相對於100質量份之縮合物(聚有機矽氧烷)係0.0001至5質量份,或0.001至1質量份,或0.01至1質量份。
又,在本發明之阻劑下層膜形成組成物中可添加流變調整劑及黏著輔助劑等。
流變調整劑可有效地提升下層膜形成組成物之流動性,黏著輔助劑可有效地提升半導體基板或阻劑與下層膜的密合性。
作為本發明之阻劑下層膜形成組成物中使用之溶劑,只要是可溶解前述之固形分的溶劑便能無特別限制地使用。作為此類溶劑,例如可舉出乙酸甲賽璐蘇、乙酸乙賽璐蘇、丙二醇、丙二醇單甲醚、丙二醇單乙醚、甲基異丁基甲醇、丙二醇單丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丙醚、二乙二醇二丁醚、丙二醇單甲醚、丙二醇二甲醚、丙二醇二乙醚、丙二醇二丙醚、丙二醇二丁醚、乳酸乙酯、乳酸丙酯、乳酸異丙酯、乳酸丁酯、乳酸異丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸異丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸異戊酯、乙酸己酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、丙
酸丁酯、丙酸異丁酯、酪酸甲酯、酪酸乙酯、酪酸丙酯、酪酸異丙酯、酪酸丁酯、酪酸異丁酯、羥基乙酸乙酯、2-羥基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基酪酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、3-甲氧基乙酸丁酯、3-甲氧基乙酸丙酯、3-甲基-3-甲氧基乙酸丁酯、3-甲基-3-甲氧基丙酸丁酯、3-甲基-3-甲氧基丁酸丁酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、環己酮、N、N-二甲基甲醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、4-甲基-2-戊醇及γ-丁內酯等。此等溶劑係可單獨或以兩種以上的組合使用。
以下針對本發明之阻劑下層膜形成組成物的使用作說明。
使用本發明之阻劑下層膜形成組成物,在基板上以塗佈法形成阻劑下層膜,或者介隔基板上之有機下層膜在其上以塗佈法形成阻劑下層膜;再於該阻劑下層膜上方形成阻劑膜(例如光阻、電子束阻劑)。接者藉由曝光及顯影以形成阻劑圖型,再使用該阻劑圖型對阻劑下層膜作乾蝕刻以進行圖型轉錄,再以圖型對基板進行加工;或者以蝕刻對有機下層膜進行圖型轉錄後,再以該有機下層膜進行基板的加工。
在形成微細圖型時,為了防止圖型坍塌,故阻劑膜厚傾向於薄化。由於阻劑之薄膜化,故用於在存在
於其下層之膜上進行轉錄圖型的乾蝕刻,若其蝕刻速度沒有比上層膜更快的話則無法圖型轉錄。在本發明中以下述順序來被覆:在基板上介隔有機下層膜或者不介隔有機下層膜,再在其上方被覆本發明之阻劑下層膜(含無機系矽系化合物),再在其上方被覆阻劑膜(有機阻劑膜)。有機系成分之膜與無機系成分之膜依據蝕刻氣體的選擇而乾蝕刻速度有著很大的差異,有機系成分之膜使用氧系氣體則乾蝕刻速度變快,無機系成分之膜使用含鹵素氣體則乾蝕刻速度變快。
例如先形成阻劑圖型,再在存在於其下層的本發明之阻劑下層膜上以含鹵素氣體進行乾蝕刻來將圖型轉錄到阻劑下層膜上,再以轉錄於該阻劑下層膜之圖型使用含鹵素氣體進行基板加工。或者使用已圖型轉錄之阻劑下層膜來對其下層之有機下層膜以氧系氣體進行進行乾蝕刻來將圖型轉錄到有機下層膜上,再以該圖型轉錄過之有機下層膜使用含鹵素氣體進行基板加工。
此處在半導體裝置製造中所使用的基板(例如矽晶圓基板、矽/二氧化矽被覆基板、氮化矽基板、玻璃基板、ITO基板、聚醯亞胺基板及低介電常數材料(low-k材料)被覆基板等)上,透過旋塗機、鍍膜機等合適的塗佈方法來塗佈本發明之阻劑下層膜形成組成物,之後透過燒成來形成阻劑下層膜。燒成的條件係從燒成溫度80℃至250℃、燒成時間0.3至60分鐘中適當地選擇,較佳為燒成溫度150℃至250℃、燒成時間0.5至2
分鐘。此處,形成之下層膜的膜厚例如為10至1000nm,或20至500nm,或50至300nm,或100至200nm。
接著,在該阻劑下層膜之上例如形成光阻層。光阻層的形成可用周知的方法,亦即藉由光阻組成物溶液之下層膜上的塗佈及燒成來進行。光阻的膜厚例如為50至10000nm,或100至2000nm,或200至1000nm。
本發明中,可在將有機下層膜於基板上成膜之後,再在其上方將本發明之阻劑下層膜成膜,接著在其上方被覆光阻。藉此使光阻之圖型寬度變窄,且即使在為了防止圖型倒塌而將光阻細薄地被覆時,亦可藉由選擇適當的蝕刻氣體來進行基板的加工。例如,可用對於光阻具有非常快速之蝕刻速度的氟系氣體作為蝕刻氣體來加工本發明之阻劑下層膜,或可用對於本發明之阻劑下層膜具有非常快速之蝕刻速度的氧系氣體作為蝕刻氣體來加工有機下層膜,進而可用對於有機下層膜具有非常快速之蝕刻速度的氟系氣體作為蝕刻氣體來進行基板的加工。
作為形成於本發明之阻劑下層膜之上的光阻,只要係可對用於曝光之光線進行感光者便無特別限制。負型光阻及正型光阻均可使用。有由酚醛清漆樹脂與1,2-萘醌二疊氮化磺酸鹽而成之正型光阻、由具有因酸分解並提升鹼溶解速度之基的黏結劑與光酸產生劑而成之化學增幅型光阻、由因酸分解並提升光阻之鹼溶解速度的低分子化合物與鹼可溶性黏結劑與光酸產生劑而成之化學增幅型光阻,以及由具有因酸分解並提升鹼溶解速度之基的
黏結劑與因酸分解並提升光阻之鹼溶解速度的低分子化合物與光酸產生劑而成之化學增幅型光阻等。例如可舉出Shipley公司製商品名APEX-E、住友化學工業(股)製商品名PAR710及信越化學工業(股)製商品名SEPR430等。又,例如可舉出Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)及Proc.SPIE,Vol.3999,365-374(2000)中所記載的含氟原子聚合物系光阻。
接著,通過特定的遮罩進行曝光。曝光中係可使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)及F2準分子雷射(波長157nm)等。曝光後,如有必要可進行曝光後加熱(postexposurebake)。曝光後加熱係從加熱溫度70℃至150℃、加熱時間0.3至10分鐘中選擇適當的條件來進行的。
又,本發明中作為阻劑更改光阻使用電子束微影用阻劑或EUV微影用阻劑。作為電子束阻劑無論負型、正型均可使用。由酸產生劑與具有因酸分解並變化鹼溶解速度之基的黏結劑而成之化學增幅型阻劑、由鹼可溶性黏結劑與酸產生劑與因酸分解並變化阻劑之鹼溶解速度的低分子化合物而成之化學增幅型阻劑、由酸產生劑與因酸分解並並變化鹼溶解速度之基團的黏結劑與因酸分解並變化阻劑之鹼溶解速度的低分子化合物而成之化學增幅型阻劑、由具有以電子束分解並變化鹼溶解速度之基團的黏結劑而成之非化學增幅型阻劑、由具有被電子束切斷並變
化鹼溶解速度之部位的黏結劑而成之非化學增幅型阻劑。在使用此等電子束阻劑的情形及在使用以電子束作為照射源之光阻的情形均同樣地可形成阻劑圖型。
又,可甲基丙烯酸酯樹脂系阻劑作為EUV阻劑。
接著以顯影液(例如鹼顯影液)進行顯影。依此,例如在使用正型光阻時,將已曝光部分的光阻去除,形成光阻的圖型。
作為顯影液係可舉出氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物水溶液,氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等之氫氧化四級銨水溶液,乙醇胺、丙基胺、乙二胺等之胺水溶液等鹼性水溶液作為例。進而,此等顯影液中可添加界面活性劑等。顯影的條件係從溫度5至50℃、時間10至600秒中適當選擇的。
又,在本發明中顯影液可使用有機溶劑,在曝光後以顯影液(溶劑)進行顯影。依此,例如在使用正型光阻時,將未曝光部分的光阻去除,形成光阻的圖型。
作為顯影液,例如可舉出乙酸甲酯、乙酸丁酯、乙酸乙酯、乙酸異丙酯、乙酸戊酯、乙酸異戊酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、丙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、乙二醇單苯醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單丙醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單苯醚乙酸酯、二乙二醇單丁醚乙酸酯、2-甲氧基乙酸丁酯、3-甲氧基乙酸丁酯、4-甲氧基乙酸丁酯、3-甲
基-3-甲氧基乙酸丁酯、3-乙基-3-甲氧基乙酸丁酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、2-乙氧基乙酸丁酯、4-乙氧基乙酸丁酯、4-丙氧基乙酸丁酯、2-甲氧基乙酸戊酯、3-甲氧基乙酸戊酯、4-甲氧基乙酸戊酯、2-甲基-3-甲氧基乙酸戊酯、3-甲基-3-甲氧基乙酸戊酯、3-甲基-4-甲氧基乙酸戊酯、4-甲基-4-甲氧基乙酸戊酯、丙二醇二乙酸酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯、乳酸丙酯、碳酸乙酯、碳酸丙酯、碳酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、丙酮酸丁酯、乙醯乙酸甲酯、乙醯乙酸乙酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、2-羥基丙酸甲酯、2-羥基丙酸乙酯、甲基-3-甲氧基丙酸酯、乙基-3-甲氧基丙酸酯、乙基-3-乙氧基丙酸酯、丙基-3-甲氧基丙酸酯等作為例。此外,此等顯影液中可添加界面活性劑等。顯影的條件係從溫度5至50℃、時間10至600秒中適當選擇的。
然後,將如此形成的光阻(上層)圖型當作保護膜以進行本發明之阻劑下層膜(中間層)的去除,接著將由已圖型化之光阻及本發明之阻劑下層膜(中間層)而成之薄膜當作保護膜以進行有機下層膜(下層)的去除。最後將已圖型化之本發明之阻劑下層膜(中間層)及有機下層膜(下層)當作保護膜,進行半導體基板的加工。
首先,藉由乾蝕刻將已去除光阻部分的本發明之阻劑下層膜(中間層)去除,使得半導體基板露出。
對於本發明之阻劑下層膜之乾蝕刻,可使用四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷、一氧化碳、氬、氧、氮、六氟化硫、二氟甲烷、三氟化氮及三氟化氯、氯、三氯硼烷及二氯硼烷等氣體。對於阻劑下層膜之乾蝕刻則以使用鹵素系氣體為佳。在藉由鹵素系氣體之乾蝕刻中,基本上由有機物質而成的光阻係難以去除的;相對於此,富含矽原子的本發明之阻劑下層膜係能以鹵素系氣體快速地去除,因此可抑制阻劑下層膜之乾蝕刻所伴隨的光阻膜厚減少。於是,其結果使得光阻可當作薄膜使用。阻劑下層膜之乾蝕刻係以氟系氣體為佳,作為氟系氣體係例如可舉出四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷及二氟甲烷(CH2F2)等。
其後將由已圖型化之光阻及本發明之阻劑下層膜而成的薄膜當作保護膜以進行有機下層膜的去除。有機下層膜(下層)較佳係以採用氧系氣體之乾蝕刻來進行,這是因為富含矽原子的本發明之阻劑下層膜不易被採用氧系氣體之乾蝕刻所去除。
最後進行半導體基板的加工。半導體基板的加工較佳係以採用氟系氣體之乾蝕刻來進行。
作為氟系氣體,例如可舉出四氟甲烷(CF4)、全氟環丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷及二氟甲烷(CH2F2)等。
又,在本發明之阻劑下層膜的上層係可在光
阻形成前先形成有機系之反射防止膜。作為在此使用之反射防止膜組成物並不特別限制,可從至今在微影製程上所慣用之物中任意選擇使用。又,可藉由慣用之方法(例如以旋塗機、鍍膜機之塗佈及燒成)來進行反射防止膜之形成。
又,塗佈了本發明之阻劑下層膜形成組成物的基板,在其表面上亦可具有以CVD法等所形成之有機系或無機系反射防止膜,且在其之上亦可形成由本發明之阻劑下層膜形成組成物而成之下層膜。
由本發明之阻劑下層膜形成組成物所形成的阻劑下層膜,又,依據在微影製程上使用之光線的波長,有具有針對該光線的吸收能力之情形。並且在該情形中,其功能可作為具有防止來自基板的反射光之效果的反射防止膜。此外,由本發明之阻劑下層膜形成組成物所形成的阻劑下層膜,亦可使用作為用以防止基板與光阻間之相互作用的層、具有防止用於光阻之材料或對光阻曝光時所生成之物質對基板產生的不良作用之機能的層、具有防止在加熱燒成時生成自基板之物質向上層光阻擴散之機能的層,以及用於減少半導體基板誘介電體層造成之光阻層毒化效果的屏蔽層等。
由阻劑下層膜形成組成物所形成之該阻劑下層膜在作為硬遮罩之功能時,在使用KrF(248nm)之曝光波長的微影技術中係選擇適合吸收KrF的發色團。雖然作為此種KrF光之發色團有已知的蒽及菲等縮環構造和萘
二甲醯亞胺構造,但此等以往之發色團由於分子量巨大而難以蒸餾純化,故在半導體製造中難以進行成為雜質之金屬管理。
本發明之組成物係使用具有在苯環中配置了O(氧原子)、S(硫原子)之構造作為發色團的水解性矽烷,該矽烷亦能吸收KrF光,並由於分子量低而能夠容易地蒸餾純化。因此,藉著使用此等發色團能將雜質金屬含量較低的水解性矽烷水解縮合物使用於上述阻劑下層膜形成組成物中,藉此能夠製造雜質較少的半導體製品。
又,由本發明之阻劑下層膜形成組成物所形成之阻劑下層膜適用於已形成用於雙鑲嵌工藝之通孔的基板,可使用作為能夠無間隙地填充通孔的填充材料。又,亦可使用作為用於使凹凸的半導體基板表面平坦化的平坦化材料。
又,EUV阻劑之下層膜除了作為硬遮罩的功能以外,亦可用於以下目的。亦即能將上述阻劑下層膜形成組成物使用作為不會與EUV阻劑互混,並且可在EUV曝光(波長13.5nm)時防止不利的曝光用光源,例如上述之UV及DUV(ArF雷射、KrF光)從基板或界面反射之EUV阻劑的下層反射防止膜,能在EUV阻劑的下層有效地防止反射。在用作EUV阻劑下層膜時,其流程可以同於光阻用下層膜的方式進行。
又,本發明亦關於式(1’)所示之矽烷。
[化29]R1 aR2 bSi(R3)4-(a+b) 式(1’)式(1’)中,R1係表示以式(2’)所示之有機基,且以Si-C鍵結與矽原子鍵結者:
式(2’)中,X及Y係各自表示氧原子或硫原子,但是X及Y不同時為相同原子,亦即在本發明中係表示X為氧原子而Y為硫原子的情形,或者X為硫原子而Y為氧原子的情形。
R6係表示可被取代之碳原子數1至10的烷基,R4係表示可被取代之碳原子數1至10的伸烷基,R5係表示可被取代之碳原子數1至10的烷基。n係表示0至4之整數。
作為上述式(1’)及式(2’)中的基團之定義中之烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、或
具有環氧基、丙烯醯基、甲基丙烯醯基、巰基、胺基或氰基之有機基、烷氧基、醯氧基、鹵素基的例,可舉出上述之例示。
[實施例]
(化合物1的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入4-(甲硫)酚25.0g、氫氧化鈉7.13g、甲苯50g、N-甲基吡咯啶酮(以下亦稱為NMP)50g,並在油浴中以130℃去除水、甲苯,同時使其反應4小時。此時滴入氯甲基三乙氧基矽烷37.94g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並獲得作為目標物之化合物1共30g。
1H-NMR(500MHz、DMSO-d6):1.19ppm(t、9H)、2.42ppm(s、3H)、3.68ppm(s、2H)、3.86ppm(q、6H)、6.95(d、2H)、7.24ppm(d、2H)
(化合物2的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入4-(三氟甲硫)酚25.0g、氫氧化鈉5.15g、甲苯50g、NMP 50g,並在油浴中以130℃去除水、甲苯,同時使其反應4小時。此時滴入氯甲基三乙氧基矽烷27.39g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並獲得作為目標物之化合物2共25g。
1H-NMR(500MHz、DMSO-d6):1.19ppm(t、9H)、3.78ppm(s、2H)、3.87ppm(q、6H)、7.13(d、2H)、7.60ppm(d、2H)
(化合物3的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入3-甲基-4-(甲硫)酚25.0g、氫氧化鈉6.48g、甲苯50g、NMP 50g,並在油浴中以130℃去除水、甲苯,同時使其反應4小時。此時滴入氯甲基三乙氧基矽烷34.49g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並獲得作為目標物之化合物3共35g。
1H-NMR(500MHz、DMSO-d6):1.20ppm(t、9H)、2.29ppm(s、3H)、2.37ppm(s、3H)、3.67ppm(s、2H)、3.86ppm(q、6H)、6.84(d、1H)、6.89(d、1H)、7.18ppm(d、1H)
(化合物4的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入3-甲氧基苯硫醇25.0g、氫氧化鈉7.13g、甲苯50g、NMP 50g,並在油浴中以130℃去除水、甲苯,同時使其反應4
小時。此時滴入氯甲基三乙氧基矽烷37.94g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並獲得作為目標物之化合物4共16g。
1H-NMR(500MHz、DMSO-d6):1.19ppm(t、9H)、2.33ppm(s、2H)、3.75ppm(s、3H)、3.83ppm(q、6H)、6.70(d、1H)、6.86(d、2H)、7.20ppm(t、1H)
(化合物5的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入4-甲氧基苯硫醇25.0g、氫氧化鈉7.13g、甲苯50g、NMP 50g,並在油浴中以130℃去除水、甲苯,同時使其反應4小時。此時滴入氯甲基三乙氧基矽烷37.94g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並
獲得作為目標物之化合物5共20g。
1H-NMR(500MHz、DMSO-d6):1.18ppm(t、9H)、2.29ppm(s、2H)、3.73ppm(s、3H)、3.82ppm(q、6H)、6.90(d、2H)、7.28ppm(d、2H)
(化合物6的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入2-(甲硫)酚25.0g、氫氧化鈉7.13g、甲苯50g、NMP 50g,並在油浴中以130℃去除水、甲苯,同時使其反應4小時。此時滴入氯甲基三乙氧基矽烷37.94g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並獲得作為目標物之化合物6共20g。
1H-NMR(500MHz、DMSO-d6):1.18ppm(t、9H)、2.37ppm(s、3H)、3.73ppm(s、2H)、3.88ppm(q、6H)、6.95(t、1H)、7.02-7.18ppm(m、3H)
(比較化合物1的合成)
在配備了磁力攪拌器的300ml三口燒瓶中加入4-甲氧基酚25.0g、氫氧化鈉8.05g、甲苯50g、NMP 50g,並在油浴中以130℃去除水、甲苯,同時使其反應4小時。此時滴入氯甲基三乙氧基矽烷42.84g,以130℃加熱攪拌4小時。讓所得之溶液回到室溫,並轉移到分液漏斗中後加入甲苯120g、水90g以洗淨有機層。重複執行3次洗淨後,在有機層添加硫酸鎂並乾燥後過濾之,再以蒸發法去除溶劑而得到粗萃取物。其後以減壓蒸餾法純化並獲得作為目標物之比較化合物1共25g。
1H-NMR(500MHz、DMSO-d6):1.19ppm(t、9H)、3.63ppm(s、2H)、3.70ppm(s、3H)、3.86ppm(q、6H)、6.85(d、2H)、6.91ppm(d、2H)
(合成例1)
將5.24g的化合物1(矽烷全體之10mol%)、四乙氧基矽烷25.86g(矽烷全體之75mol%)、甲基三乙氧基矽烷4.43g(矽烷全體之15mol%)、丙酮53.29g放入300ml的燒瓶中,以磁力攪拌器攪拌混合溶液並同時將0.01mol/l之鹽酸11.19g滴進混合溶液中。添加後,將燒瓶移到已調整至85℃的油浴中,在加溫回流下使其反應240分鐘。其後將反應溶液冷卻至室溫,在反應溶液中加入丙二醇單甲醚乙酸鹽72.00g,並餾出作為反應副生成物之乙醇、水、鹽酸、丙酮,再將其濃縮而獲得水解縮合物(聚合物)丙二醇單甲醚乙酸鹽溶液。在140℃中調整至固形殘留物換算的30重量百分比,所得之聚合物相當於式(3-1),以GPC經聚苯乙烯換算之重量平均分子量為Mw1500。該聚合物稱作P1。
合成例2至10及比較合成例1至2係與合成例1相同的操作方式進行。各成分及其投入量如表1所示。
以合成例2所得之聚合物係相當於式(3-2)且重量平均分子量為1800。該聚合物稱作P2。
以合成例3所得之聚合物係相當於式(3-3)且重量平均分子量為1800。該聚合物稱作P3。
以合成例4所得之聚合物係相當於式(3-4)且重量平均分子量為1600。該聚合物稱作P4。
以合成例5所得之聚合物係相當於式(3-5)且重量平均分子量為1700。該聚合物稱作P5。
以合成例6所得之聚合物係相當於式(3-6)且重量平均分子量為1700。該聚合物稱作P6。
以合成例7所得之聚合物係相當於式(3-7)且重量平均分子量為1700。該聚合物稱作P7。
以合成例8所得之聚合物係相當於式(3-8)且重量平均分子量為1700。該聚合物稱作P8。
以合成例9所得之聚合物係相當於式(3-9)且重量平均分子量為2000。該聚合物稱作P9。
以合成例10所得之聚合物係相當於式(3-9)且重量平均分子量為1600。該聚合物稱作P10。
以比較合成例1所得之聚合物係相當於式(4-1)且重量平均分子量為1700。該聚合物稱作RP1。
以比較合成例2所得之聚合物相當於式(3-6),且重量平均分子量為1600。該聚合物稱作RP2。
表1中,TEOS係表示四乙氧基矽烷,MTEOS係表示甲基三乙氧基矽烷,MeOPSP係表示3-(4-甲氧基苯基磺醯基)丙基三乙氧基矽烷,MeOBSA係表示4-甲氧
基-N-(3-(三乙氧基矽烷基)丙基)苯磺醯胺。酸係表示0.01M濃度之HCl水溶液。
(阻劑下層膜形成組成物之調製)
將在上述合成例1至10及比較合成例1至2所得之含矽聚合物、酸、硬化觸媒、添加劑、溶劑、水以表2所示之比例混合,並藉由以0.02μm之氟樹脂製過濾器進行過濾,分別調製出阻劑下層膜形成組成物的溶液。表2中聚合物的比例並非以聚合物溶液的質量,而是以聚合物本身的質量表示。
表2中的馬來酸為MA,硬化觸媒C1為N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑(簡稱IMIDTEOS),硬化觸媒C2為苄基三乙基銨氯化物(簡稱BTEAC),硬化觸媒C3為馬來酸三苯基鋶(簡稱TPSMA),硬化觸媒C4為三苯基鋶硝酸鹽(簡稱TPSNO3),添加劑A1為三苯基鋶三氟甲基磺酸鹽(簡稱TPS105),添加劑A2為R-40LM(DIC(股)製,成分係氟系界面活性劑),溶劑S1為丙二醇單甲醚(簡稱PGME),溶劑S2為丙二醇單乙醚(簡稱PGEE),溶劑S3為丙二醇單甲醚乙酸鹽(簡稱PGMEA),水係使用超純水。各添加量係以質量份表示。
(有機下層膜(A層)形成組成物的調製)
在氮氣下,在100ml四口燒瓶中加入咔唑(6.69g、0.040mol、東京化成工業(股)製)、9-茀酮(7.28g、0.040mol、東京化成工業(股)製)、對甲苯磺酸一水合物(0.76g、0.0040mol、東京化成工業(股)製),將1,4-二噁烷(6.69g、關東化學(股)製)裝入並攪拌,升溫至100℃使其溶解並開始聚合。24小時後將其放冷至60℃後,加入氯仿(34g、關東化學(股)製)稀釋之,並使其再沉澱至甲醇(168g、關東化學(股)製)中。過濾所得之沉澱物,用減壓乾燥機以80℃乾燥24小時,得到了作為標的之聚合物(式(E-1),以下簡稱PCzFL)9.37g。
PCzFL之1H-NMR之測量結果如下:
1H-NMR(400MHz,DMSO-d6):δ7.03-7.55(br、12H)、δ7.61-8.10(br、4H)、δ11.18(br、1H)。
PCzFL之以GPC經聚苯乙烯換算所測量的重量平均分子量Mw為2800,多分散度Mw/Mn為1.77。
在所得之樹脂20g中混合作為交聯劑之四甲氧基甲基甘脲(三井Cytec(股)製、商品名Powderlink
1174)3.0g、作為觸媒之吡啶鎓對甲苯磺酸鹽0.30g、作為界面活性劑之MEGAFAC R-40LM(DIC(股)製、商品名)0.06g,並溶解於丙二醇單甲醚乙酸鹽88g中以作為溶液。其後使用0.10μm孔徑之聚乙烯製微型過濾器進行過濾,接著使用0.05μm孔徑之聚乙烯製微型過濾器進行過濾,調製出用於多層膜之微影製程的有機下層膜(A層)形成組成物溶液。
(光學常數測量)
使用旋塗機,將在實施例1至14、比較例1至2調製的含Si阻劑下層膜形成組成物分別塗佈於矽晶圓上。在加熱板上以215℃加熱1分鐘,形成了含Si阻劑下層膜(膜厚0.05μm)。並且,對該等阻劑下層膜使用光譜式橢圓偏光儀(J.A.Woollam公司製、VUV-VASEVU-302),測量對波長193及248nm的折射率(n值)及光學吸光係數(亦稱作k值、衰減係數),結果如表3所示。
(乾蝕刻速度的測量)
用於乾蝕刻速度量測的蝕刻器及蝕刻氣體係使用下者:
ES401(日本Scientific製):CF4
RIE-10NR(Samco製):O2
使用旋塗機,將在實施例1至14、比較例1至2調製的含Si阻劑下層膜形成組成物溶液塗佈於矽晶圓上。在加熱板上以215℃加熱1分鐘,形成了含Si阻劑下層膜(B層)。又,同樣地針對有機下層膜(A層)形成組成
物亦使用旋塗機,在矽晶圓上形成有機下層膜(A層)(膜厚0.20μm)。使用作為蝕刻氣體之O2氣體並測量乾蝕刻速度,並比較有機下層膜(A層)之乾蝕刻速度與實施例1至14、比較例1至2之含Si阻劑下層膜之乾蝕刻速度。氧系氣體(O2氣體)耐性係以〔含Si阻劑下層膜(B層)〕/〔有機下層膜(A層)〕之蝕刻速率比表示(表4)。
又,使用旋塗機,將在實施例1至14、比較例1至2調製的含Si阻劑下層膜形成組成物溶液塗佈於矽晶圓上。在加熱板上以215℃加熱1分鐘,形成了含Si阻劑下層膜(B層)。又,同樣地針對有機下層膜(A層)形成組成物亦使用旋塗機,在矽晶圓上形成有機下層膜(A層)(膜厚0.20μm)。並且,使用氟系氣體(CF4氣體)並測量蝕刻速率(蝕刻速度:nm/分)。與上述相同之氟系氣體(CF4氣體)耐性係以〔含Si阻劑下層膜(B層)〕/〔有機下層膜(A層)〕之蝕刻速率比表示(表4)。
[圖型形狀之評估]
將有機下層膜(A層)形成組成物塗佈於矽晶圓上,並在加熱板上以240℃烘焙60秒,得到了膜厚200nm之有機下層膜(A層)。在其上方以旋塗機塗佈實施例1至14以及比較例1至2調製的含Si阻劑下層膜形成組成物,其後在215℃的加熱板上烘焙1分鐘,形成了阻劑下
層膜(膜厚0.06μm)。在該阻劑下層膜上以旋塗機塗佈市售之光阻溶液(東京應化工業(股)製、商品名:TDUR-P3435LP),並在90℃的加熱板上加熱1分鐘以形成光阻膜(膜厚0.25μm)。接著使用(股)Nikon製NSR-S205C鏡頭掃描方式步進器(波長248nm、NA:0.75、σ:0.85(CONVENTIONAL)),通過將顯影後之阻劑圖型線寬及其線間寬度設定為0.16μm的遮罩來進行曝光。其後在110℃的加熱板上進行1分鐘「曝光後加熱」。冷卻後,使用作為顯影液之2.38%四甲基氫氧化銨水溶液進行顯影,並評估顯影後的阻劑形狀(表4)。
[產業上之可利用性]
本發明之阻劑下層膜形成組成物係含有具有苯環中配置了O(氧原子)、S(硫原子)構造作為發色團的水解性矽烷。此矽烷亦能夠吸收KrF光,且因分子量低而能夠容易地蒸餾純化。因此,由含有使用了此等發色團且雜質金屬含量較低之水解性矽烷水解縮合物的上述阻劑下層膜成組成物,能夠進行雜質較少之半導體製品的製造。
Claims (7)
- 一種式(1’)所示之矽烷,R1 aR2 bSi(R3)4-(a+b) 式(1’)式(1’)中,R1表示式(2’)所示之有機基且為藉由Si-C鍵結與矽原子鍵結者,
- 一種式(1’)所示之矽烷,R1 aR2 bSi(R3)4-(a+b) 式(1’)式(1’)中,R1表示式(2’)所示之有機基且為藉由Si-C鍵結與矽原子鍵結者,
- 如請求項2或3之矽烷,其中n為1~4之整數。
- 一種微影用阻劑下層膜形成組成物,其包含如請求項1~4中任一項之矽烷。
- 一種半導體裝置之製造方法,其包含下述步驟:將如請求項5之阻劑下層膜形成組成物塗佈於半導體 基板進行燒成形成阻劑下層膜的步驟、於前述下層膜上塗佈阻劑組成物形成阻劑膜的步驟、將前述阻劑膜曝光的步驟、曝光後將阻劑進行顯影而得到阻劑圖型的步驟、藉由前述阻劑圖型蝕刻阻劑下層膜的步驟,及藉由圖型化之阻劑下層膜加工半導體基板的步驟。
- 一種半導體裝置之製造方法,其包含下述步驟:於半導體基板上形成有機下層膜的步驟、於其上塗佈如請求項5之阻劑下層膜形成組成物進行燒成形成阻劑下層膜的步驟、於前述阻劑下層膜上塗佈阻劑組成物形成阻劑膜的步驟、將前述阻劑膜曝光的步驟、曝光後將阻劑進行顯影而得到阻劑圖型的步驟、藉由前述阻劑圖型蝕刻阻劑下層膜的步驟、藉由圖型化之阻劑下層膜蝕刻有機下層膜的步驟,及藉由圖型化之有機下層膜加工半導體基板的步驟。
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