JP2013079232A - 光酸発生剤およびこれを含むフォトレジスト - Google Patents
光酸発生剤およびこれを含むフォトレジスト Download PDFInfo
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- JP2013079232A JP2013079232A JP2012210465A JP2012210465A JP2013079232A JP 2013079232 A JP2013079232 A JP 2013079232A JP 2012210465 A JP2012210465 A JP 2012210465A JP 2012210465 A JP2012210465 A JP 2012210465A JP 2013079232 A JP2013079232 A JP 2013079232A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 18
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 17
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000002892 organic cations Chemical class 0.000 claims abstract description 12
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 10
- 150000001767 cationic compounds Chemical class 0.000 claims abstract description 8
- 229910001411 inorganic cation Inorganic materials 0.000 claims abstract description 8
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- 125000005647 linker group Chemical group 0.000 claims abstract description 7
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract description 7
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- 229920000642 polymer Polymers 0.000 claims description 17
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- 125000003118 aryl group Chemical group 0.000 claims description 11
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 7
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 6
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- 125000004991 fluoroalkenyl group Chemical group 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
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- 125000000524 functional group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 235000012431 wafers Nutrition 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
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- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 150000008053 sultones Chemical class 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- QDHFHIQKOVNCNC-UHFFFAOYSA-M butane-1-sulfonate Chemical compound CCCCS([O-])(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-M 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 3
- 239000012953 triphenylsulfonium Substances 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
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- PLGPYICAYSTZLQ-UHFFFAOYSA-N 4-bromo-3,3,4,4-tetrafluorobutane-1-sulfonyl chloride Chemical compound FC(F)(Br)C(F)(F)CCS(Cl)(=O)=O PLGPYICAYSTZLQ-UHFFFAOYSA-N 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
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- SWKVXOGJOAPZTH-UHFFFAOYSA-N (1-propan-2-yl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2C(OC(=O)C(C)=C)C1(C(C)C)C3 SWKVXOGJOAPZTH-UHFFFAOYSA-N 0.000 description 1
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- GSWBUNOTNQDUDL-UHFFFAOYSA-N (3-hydroxy-1-adamantyl)methyl 4-bromo-3,3,4,4-tetrafluorobutane-1-sulfonate Chemical compound C1C(C2)CC3CC1(O)CC2(COS(=O)(=O)CCC(F)(F)C(F)(F)Br)C3 GSWBUNOTNQDUDL-UHFFFAOYSA-N 0.000 description 1
- ASHCDEYFCNWSTR-UHFFFAOYSA-N 1,4-dibromo-1,1,2,2-tetrafluorobutane Chemical compound FC(F)(Br)C(F)(F)CCBr ASHCDEYFCNWSTR-UHFFFAOYSA-N 0.000 description 1
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- JIXHYWCLUOGIMM-UHFFFAOYSA-N 2-(2-methoxyethoxy)propanoic acid Chemical compound COCCOC(C)C(O)=O JIXHYWCLUOGIMM-UHFFFAOYSA-N 0.000 description 1
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 1
- FORAJDRXEYKDFJ-UHFFFAOYSA-N 3-(hydroxymethyl)adamantan-1-ol Chemical compound C1C(C2)CC3CC2(O)CC1(CO)C3 FORAJDRXEYKDFJ-UHFFFAOYSA-N 0.000 description 1
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- QSUJHKWXLIQKEY-UHFFFAOYSA-N CC(C(OC(CCO1)C1=O)=O)=C Chemical compound CC(C(OC(CCO1)C1=O)=O)=C QSUJHKWXLIQKEY-UHFFFAOYSA-N 0.000 description 1
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- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
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- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
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- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- CYVOZVLWADJEEB-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC(CO)(CO)CO CYVOZVLWADJEEB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 150000002847 norbornane derivatives Chemical class 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 description 1
- 229950003332 perflubutane Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 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
- 238000004513 sizing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- LLFNZCQAFAVOLK-UHFFFAOYSA-N tert-butyl 4-oxo-1h-pyridine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC(O)=CC=N1 LLFNZCQAFAVOLK-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- SXPSZIHEWFTLEQ-UHFFFAOYSA-N tröger's base Chemical compound C12=CC=C(C)C=C2CN2C3=CC=C(C)C=C3CN1C2 SXPSZIHEWFTLEQ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
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- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
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- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
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- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
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- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
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- C07D497/18—Bridged systems
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Abstract
【解決手段】式(I):[A−(CHR1)p]k−(L)−(CH2)m−(C(R2)2)n−SO3 −Z+(I)(式中、Aは置換されているかもしくは非置換の単環式、多環式もしくは縮合多環式の環式脂肪族基であり、R1はH、単結合または置換されているかもしくは非置換のC1−30アルキル基であり、R2はH、F、もしくはC1−4フルオロアルキルであり、Lはスルホナート基、スルホンアミド基またはC1−30スルホナートもしくはスルホンアミド含有基を含む連結基であり、Zは有機もしくは無機カチオンであり、pは0〜10の整数であり、kは1もしくは2であり、mは0以上の整数であり、並びにnは1以上の整数である)を有する光酸発生剤化合物。
【選択図】なし
Description
本出願は2011年9月30日に出願された米国仮出願第61/541,764号に対する優先権を主張し、その仮出願の内容はその全体が参照によって本明細書に組み込まれる。
これまで以上に小さな論理およびメモリトランジスタを形成する目的で、マイクロリソグラフィプロセスにおいて高い品質およびより小さなフィーチャサイズを達成するために、193nm液浸リソグラフィのような進歩したリソグラフィ技術が開発されてきた。高い露光寛容度(EL)および広い焦点深度(DOF)のような良好なプロセス制御許容度を依然として維持しつつ、最も低いラインエッジラフネス(LER)およびライン幅ラフネス(LWR)の双方を提供するフォトレジストのために、並びにマイクロリソグラフィプロセスに使用される像形成されるフォトレジストにおいて、この両方で、より小さな限界寸法(critical dimension;CD)を達成することが重要である。
[A−(CHR1)p]k−(L)−(CH2)m−(C(R2)2)n−SO3 −Z+ (I)
(式中、Aは置換されているかもしくは非置換の単環式、多環式もしくは縮合多環式のC5以上の環式脂肪族基であり、R1はH、単結合または置換されているかもしくは非置換のC1−30アルキル基であって、R1が単結合の場合にはR1はAの炭素原子に共有結合されている、各R2は独立してH、F、もしくはC1−4フルオロアルキルであって、少なくとも1つのR2は水素ではなく、Lはスルホナート基、スルホンアミド基またはC1−30スルホナートもしくはスルホンアミド含有基を含む連結基であり、Zは有機もしくは無機カチオンであり、pは0〜10の整数であり、kは1もしくは2であり、mは0以上の整数であり、並びにnは1以上の整数である)を有する光酸発生剤によって克服されうる。
M+−O−SO2−(C(R2)2)n−(CH2)m−X
(式中、各R2は独立してH、F、C1−4フルオロアルキルであって、少なくとも1つのR2は水素ではなく、Xはハロゲン、スルホナートもしくはカルボキシラートを含む官能基であり、M+は有機もしくは無機カチオンであり、mは0以上の整数であり、並びにnは1以上の整数である)
を有する化合物も開示される。
[A−(CHR1)p]k−(L)−(CH2)m−(C(R2)2)n−SO3 −Z+ (I)
を有するものが挙げられ、式中、Aは置換されているかもしくは非置換の単環式、多環式もしくは縮合多環式のC5以上の環式脂肪族基である。本明細書において使用される場合、「置換されている」とは置換基、例えば、ハロゲン(すなわち、F、Cl、Br、I)、ヒドロキシ、アミノ、チオール、カルボキシル、カルボキシラート、アミド、ニトリル、チオール、スルフィド、ジスルフィド、ニトロ、C1−10アルキル、C1−10アルコキシ、C6−10アリール、C6−10アリールオキシ、C7−10アルキルアリール、C7−10アルキルアリールオキシ、または前記のものの少なくとも1種を含む組み合わせを含むことを意味する。本明細書において、前記式に関して開示される何らかの基もしくは構造は、他に特定されない限りは、または生じる構造の望まれる特性にこのような置換が有意に悪影響を及ぼさないであろう限りは、そのように置換されていてもよいことが理解されるであろう。本明細書において使用される場合、接頭辞「ハロ−」は、その基がハロゲンもしくはその組み合わせ(F、Cl、Br、I)を含むことを意味する。好ましいハロゲンはフッ素である。場合によっては、Aはヘテロ原子、例えば、O、S、N、F、または前述のものの少なくとも1種を含む組み合わせをさらに含む。例えば、Aが酸素を含む場合には、Aの構造はエーテルもしくはラクトン部分を含むことができ、またはAが硫黄を含む場合にはAの構造はスルトンもしくはスルホナートもしくはスルファム(sulfam)部分を含むことができる。
A−(CHR1)p−O−SO2−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIa)
A−(CHR1)p−SO2−O−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIb)
式中、A、R1、R2、p、m、nおよびZは式(I)について定義された通りである。
A−(CHR1)p−N(R3)−SO2−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIIa)
A−(CHR1)p−SO2−N(R3)−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIIb)
式中、A、R1、R2、p、m、nおよびZは式(I)について定義された通りであり、並びにR3はH、C1−20アルキル基、もしくはA−(CHR1)p−である。R3がA−(CHR1)p−である場合、この基は別の基A−(CHR1)p−と同じであっても良いしまたは異なっていてもよいことが認識されるであろう。
M+−O−SO2−(C(R2)2)n−(CH2)m−X (XXI)
式中、各R2は独立してH、F、C1−4フルオロアルキルであり、少なくとも1つのR2は水素ではなく、Xはハロゲン、スルホナート、スルホンアミドまたはカルボキシラートを含む官能基であり、M+は有機もしくは無機カチオンであり、mは0以上の整数であり、並びにnは1以上の整数である。よって、(XXI)の式は、式(I)における連結基Lの基礎構造、並びに超酸塩のハロゲン化部分の構造を含むことが認識されるであろう。
フォトレジストは、有機反射防止膜(AR(商標)77、ロームアンドハースエレクトロニックマテリアルズLLC)を有する200mmシリコンウェハ上にスピンコートされ、110℃で60秒間ベークされて、100nm厚さのレジスト膜を形成した。フォトレジストは、ASML/1100露光ツール(ASMLにより製造)を用いて、0.75の開口数(NA)で、0.89/0.64のアウター/インナーシグマおよび焦点オフセット/ステップ0.10/0.05での環状照明下で、ArFエキシマレーザー放射線(193nm)で露光された。フィーチャを像形成するために、90nmのライン幅および180nmのピッチをターゲットにするライン−スペースパターンマスクが使用された。
Claims (10)
- 式(I):
[A−(CHR1)p]k−(L)−(CH2)m−(C(R2)2)n−SO3 −Z+ (I)
(式中、Aは置換されているかもしくは非置換の単環式、多環式もしくは縮合多環式のC5以上の環式脂肪族基であって、場合によってはO、S、N、Fもしくは前述のものの少なくとも1種を含む組み合わせを含んでおり、
R1はH、単結合または置換されているかもしくは非置換のC1−30アルキル基であって、R1が単結合の場合にはR1はAの炭素原子に共有結合されており、
各R2は独立してH、F、もしくはC1−4フルオロアルキルであって、少なくとも1つのR2は水素ではなく、
Lはスルホナート基、スルホンアミド基またはC1−30スルホナートもしくはスルホンアミド含有基を含む連結基であり、
Zは有機もしくは無機カチオンであり、
pは0〜10の整数であり、kは1もしくは2であり、mは0以上の整数であり、並びにnは1以上の整数である)
を有する化合物。 - 式(IIa)または(IIb):
A−(CHR1)p−O−SO2−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIa)
A−(CHR1)p−SO2−O−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIb)
(式中、A、R1、R2、p、m、nおよびZは式(I)について定義された通りである)
を有する請求項1に記載の化合物。 - 式(IIIa)もしくは(IIIb):
A−(CHR1)p−N(R3)−SO2−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIIa)
A−(CHR1)p−SO2−N(R3)−(CH2)m−(C(R2)2)n−SO3 −Z+ (IIIb)
(式中、A、R1、R2、p、m、nおよびZは式(I)について定義された通りであり、並びにR3はH、C1−20アルキル基、もしくはA−(CHR1)p−である)を有する請求項1に記載の化合物。 - 前記カチオンが式(XIV)、(XV)もしくは(XVI):
R6、R7、R8およびR9はそれぞれ独立してH、ハロゲン、C1−20アルキル、C1−20フルオロアルキル、C1−20アルコキシ、C1−20フルオロアルコキシ、C1−20チオアルコキシ、C1−20フルオロチオアルコキシ、C1−20アルコキシカルボニル、C1−20フルオロアルコキシカルボニル、C1−20チオアルコキシカルボニル、C1−20フルオロチオアルコキシカルボニル、C3−20シクロアルキル、C3−20フルオロシクロアルキル、C3−20シクロアルコキシ、C3−20フルオロシクロアルコキシ、C2−20アルケニル、C2−20フルオロアルケニル、C6−20アリール、C6−20フルオロアリール、C6−20アリールオキシ、C6−20フルオロアリールオキシ、C5−20ヘテロアリール、C5−20ヘテロアリールオキシ、C5−20ヘテロアリールオキシ、C7−20アラルキル、C7−20フルオロアラルキル、C7−20アラルキルオキシ、C7−20フルオロアラルキルオキシ、C6−20ヘテロアラルキル、またはC6−20ヘテロアラルキルオキシであり、R6、R7、R8およびR9はそれぞれ独立して置換されていないか、または酸不安定基、塩基不安定基、もしくは塩基可溶性基を含むようにさらに置換されており、並びに
qは1〜5の整数であり、rは0〜3の整数であり、sは0〜4の整数であり、tは0〜4の整数であり、およびaは0〜4の整数である)
のものである請求項5に記載の化合物。 - 式:
M+−O−SO2−(C(R2)2)n−(CH2)m−X
(式中、各R2は独立してH、F、C1−4フルオロアルキルであり、少なくとも1つのR2は水素ではなく、
Xはハロゲン、スルホナートまたはカルボキシラートを含む官能基であり、
M+は有機もしくは無機カチオンであり、
mは0以上の整数であり、並びにnは1以上の整数である)
を有する化合物。 - 酸感受性ポリマー、および
請求項1〜7のいずれか1項の化合物、
を含むフォトレジスト組成物。 - (a)基体の表面上にパターン形成される1以上の層を有する基体;並びに(b)前記パターン形成される1以上の層上の、請求項9のフォトレジスト組成物の層;を含むコーティングされた基体。
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CN101987880A (zh) * | 2009-08-04 | 2011-03-23 | 锦湖石油化学株式会社 | 新型共聚物和含有该共聚物的光刻胶组合物 |
WO2011104127A1 (en) * | 2010-02-24 | 2011-09-01 | Basf Se | Latent acids and their use |
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TW201319024A (zh) | 2013-05-16 |
CN103086934A (zh) | 2013-05-08 |
JP2017122100A (ja) | 2017-07-13 |
CN106831507A (zh) | 2017-06-13 |
JP6728429B2 (ja) | 2020-07-22 |
US9146470B2 (en) | 2015-09-29 |
TWI503305B (zh) | 2015-10-11 |
JP2019112435A (ja) | 2019-07-11 |
US20130084525A1 (en) | 2013-04-04 |
US20150056558A1 (en) | 2015-02-26 |
KR20130035958A (ko) | 2013-04-09 |
KR101450039B1 (ko) | 2014-10-13 |
US8900794B2 (en) | 2014-12-02 |
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