JP5742662B2 - 含フッ素スルホン酸塩類、光酸発生剤、レジスト組成物及びそれを用いたパターン形成方法 - Google Patents
含フッ素スルホン酸塩類、光酸発生剤、レジスト組成物及びそれを用いたパターン形成方法 Download PDFInfo
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- JP5742662B2 JP5742662B2 JP2011233940A JP2011233940A JP5742662B2 JP 5742662 B2 JP5742662 B2 JP 5742662B2 JP 2011233940 A JP2011233940 A JP 2011233940A JP 2011233940 A JP2011233940 A JP 2011233940A JP 5742662 B2 JP5742662 B2 JP 5742662B2
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- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005394 methallyl group Chemical group 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- YEHTUHUPOVGSCH-UHFFFAOYSA-N methyl 2-(1-adamantyl)-2,2-difluoroacetate Chemical compound C1C(C2)CC3CC2CC1(C(F)(F)C(=O)OC)C3 YEHTUHUPOVGSCH-UHFFFAOYSA-N 0.000 description 1
- ISOAYJWHCPFRRA-UHFFFAOYSA-N methyl 2-(1-adamantyloxysulfonyl)-2,2-difluoroacetate Chemical compound C1C(C2)CC3CC2CC1(OS(=O)(=O)C(F)(F)C(=O)OC)C3 ISOAYJWHCPFRRA-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
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- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
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- VYHUMZYFJVMWRC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methylprop-2-enamide Chemical compound OCCN(C)C(=O)C=C VYHUMZYFJVMWRC-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
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- UIWMMUSDNIMEBK-UHFFFAOYSA-N naphthalen-2-yl(diphenyl)sulfanium Chemical compound C1=CC=CC=C1[S+](C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 UIWMMUSDNIMEBK-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
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- 125000005574 norbornylene group Chemical group 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
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- PEAQLBQIIXRSKF-UHFFFAOYSA-N phenyl-(4-prop-2-enoyloxyphenyl)iodanium Chemical compound C1=CC(OC(=O)C=C)=CC=C1[I+]C1=CC=CC=C1 PEAQLBQIIXRSKF-UHFFFAOYSA-N 0.000 description 1
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- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
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- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000005469 synchrotron radiation Effects 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
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GJWMYLFHBXEWNZ-UHFFFAOYSA-N tert-butyl (4-ethenylphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(C=C)C=C1 GJWMYLFHBXEWNZ-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- VRAWXSCCKYEDOG-UHFFFAOYSA-N tribenzylsulfanium Chemical compound C=1C=CC=CC=1C[S+](CC=1C=CC=CC=1)CC1=CC=CC=C1 VRAWXSCCKYEDOG-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- CECPFQZDKXOJLX-UHFFFAOYSA-N tris(3,4-ditert-butylphenyl)sulfanium Chemical compound C1=C(C(C)(C)C)C(C(C)(C)C)=CC=C1[S+](C=1C=C(C(=CC=1)C(C)(C)C)C(C)(C)C)C1=CC=C(C(C)(C)C)C(C(C)(C)C)=C1 CECPFQZDKXOJLX-UHFFFAOYSA-N 0.000 description 1
- KCKZNRIIFSOYQK-UHFFFAOYSA-N tris(3-tert-butylphenyl)sulfanium Chemical compound CC(C)(C)C1=CC=CC([S+](C=2C=C(C=CC=2)C(C)(C)C)C=2C=C(C=CC=2)C(C)(C)C)=C1 KCKZNRIIFSOYQK-UHFFFAOYSA-N 0.000 description 1
- DMJFWVWYOPMJIK-UHFFFAOYSA-N tris[3,4-bis[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound C1=C(OC(C)(C)C)C(OC(C)(C)C)=CC=C1[S+](C=1C=C(OC(C)(C)C)C(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C(OC(C)(C)C)=C1 DMJFWVWYOPMJIK-UHFFFAOYSA-N 0.000 description 1
- HENPLGIMUIZOJQ-UHFFFAOYSA-N tris[3-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound CC(C)(C)OC1=CC=CC([S+](C=2C=C(OC(C)(C)C)C=CC=2)C=2C=C(OC(C)(C)C)C=CC=2)=C1 HENPLGIMUIZOJQ-UHFFFAOYSA-N 0.000 description 1
- YNIMTIPTLNZOMC-UHFFFAOYSA-N tris[4-(dimethylamino)phenyl]sulfanium Chemical compound C1=CC(N(C)C)=CC=C1[S+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 YNIMTIPTLNZOMC-UHFFFAOYSA-N 0.000 description 1
- PNXQORBBJALXKA-UHFFFAOYSA-N tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 PNXQORBBJALXKA-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
- C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
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Description
[発明3]
一般式(2)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜10の整数かつqが0〜8の整数である繰り返し単位を有する発明2のレジスト組成物。
一般式(2)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜4の整数かつqが0または1である繰り返し単位を有する発明2または3のレジスト組成物。
ベース樹脂が、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル類、含フッ素ビニルエーテル類、アリルエーテル類、含フッ素アリルエーテル類、アクリルアミド類、メタクリルアミド類、ビニルエステル類、アリルエステル類、オレフィン類、含フッ素オレフィン類、ノルボルネン化合物および含フッ素ノルボルネン化合物からなる群より選ばれた一種の単量体を重合させた高分子重合体、又は、前記単量体の二種以上を共重合させた高分子共重合体であることを特徴とする、発明2〜4のレジスト組成物。
ベース樹脂が、高エネルギー線露光前は現像液に不溶または難溶であって、露光後光酸発生剤の作用により現像液に可溶となる樹脂である発明2〜5のレジスト組成物。
ベース樹脂が、高エネルギー線露光前は現像液に可溶であって、露光後光酸発生剤の作用により現像液に難溶または不溶となる樹脂である発明2〜5のレジスト組成物。
発明1〜7のレジスト組成物を基板上に塗布する工程と、加熱処理後フォトマスクを介して波長300nm以下の高エネルギー線で露光する工程と、必要に応じて加熱処理した後、現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
露光する工程が、波長193nmのArFエキシマレーザーを用い、レジスト組成物を塗布した基板と投影レンズの間に水、もしくは空気の屈折率より高い屈折率を有する水以外の液体を挿入する液浸リソグラフィ法であることを特徴とする発明8のパターン形成方法。
[発明12]
一般式(4)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜10の整数かつqが0〜8の整数である繰り返し単位を有する発明10の含フッ素スルホン酸塩。
一般式(4)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜4の整数かつqが0または1である繰り返し単位を有する発明10の含フッ素スルホン酸塩。
発明11の含フッ素スルホン酸塩からなる光酸発生剤。
[4.4.0.12,517,10]ドデシル基、2−オキソ−ボルニル基等を挙げることができる。
本発明の一般式(1)で表される構造を有する含フッ素スルホン酸塩として、下記一般式(2)で表される含フッ素スルホン酸オニウム塩が好ましい例として挙げられる。この含フッ素スルホン酸オニウム塩は、高エネルギー線に感応して非常に酸強度の大きい含フッ素スルホン酸を発生する能力を有することから、含フッ素スルホン酸オニウム塩は光酸発生剤として有用である。
次いで、上述した、一般式(1)で表されるアニオンを有する含フッ素スルホン酸塩の製造方法について述べる。一般式(1)で表されるアニオンを有する含フッ素スルホン酸塩は、一般式(2)で表される含フッ素スルホン酸オニウム塩と同様に製造することができる。以下の製造方法の説明においてQ+をM+と読み替えることができる。
R1COOH (16)
(式中、R1は前記一般式(1)におけるR1と同義である。)で表されるカルボン酸、下記一般式(17)
R1COX´ (17)
(式中、R1は前記一般式(1)におけるR1と同義である。X´はフッ素、塩素、臭素又はヨウ素を表す。)で表されるカルボン酸ハロゲン化物あるいは下記一般式(18)
(R1CO)2O (18)
(式中、R1は前記一般式(1)におけるR1と同義である。)で表されるカルボン酸無水物のいずれかを表す。
R1OCOX´ (19)
(式中、R1は前記一般式(1)におけるR1と同義である。X´はフッ素、塩素、臭素又はヨウ素を表す。)で表されるハロゲン化炭酸アルキル等を表す。
R1N=C=O (20)
(式中、R1は前記一般式(1)におけるR1と同義である。)で表されるイソシアナートを表す。
R1SO3H (21)
(式中、R1は前記一般式(1)におけるR1と同義である。)で表されるスルホン酸、下記一般式(22)
R1SO2X´ (22)(式中、R1は前記一般式(1)におけるR1と同義である。X´はフッ素、塩素、臭素又はヨウ素を表す。)で表されるスルホン酸ハロゲン化物あるいは下記一般式(23)
(R1SO2)2O (23)
(式中、R1は前記一般式(1)におけるR1と同義である。)で表されるスルホン酸無水物のいずれかを表す。
第1工程について説明する。第1工程は、一般式(13)で表されるヒドロキシフルオロアルカンスルホン酸オニウム塩に一般式(14)で表されるトリフルオロメチルピルビン酸誘導体を付加させる工程である。この付加反応は、一般式(13)で表されるヒドロキシフルオロアルカンスルホン酸オニウム塩に一般式(14)で表されるトリフルオロメチルピルビン酸誘導体を、酸触媒存在下、あるいは無触媒条件下で反応させて行うことができる。
次いで第2工程について説明する。第2工程は、一般式(5)で表される含フッ素スルホン酸オニウム塩と一般式(15)で表される化合物を反応させ、一般式(2)で表される含フッ素スルホン酸オニウム塩を合成する工程である。
本発明のレジスト組成物は、ベース樹脂、酸発生剤、溶剤を含み、塩基性化合物、可塑剤、レべリング剤、界面活性剤、付加的樹脂、安定剤、着色剤、増粘剤、消泡剤、相溶化剤、密着剤、酸化防止剤などの種々添加剤を含むことができる。
本発明のレジスト組成物に配合するベース樹脂について説明する。ベース樹脂は、光照射により酸発生剤から発生した酸により酸不安定性基が脱離して、光照射前アルカリ水溶液に不溶解であった樹脂が可溶性に変化する樹脂、または、光照射により酸発生剤から発生した酸により中性ヒドロキシル基が架橋剤と反応して、光照射前アルカリ水溶液に溶解性であった樹脂が不溶性または難溶性に変化する樹脂であり、それぞれポジ型またはネガ型レジストに用いられる。
ベース樹脂は、下記一般式(24−1)、(24−2)または(24−3)で表される繰り返し単位(A)または繰り返し単位(B)を少なくとも含み、さらに繰り返し単位(C)を含むことができる。
−(CR10R11)m−
−(CR10R11)m−C(=O)−O−(CR10R11)n−
−(CR10R11)m−C(=O)−O−(CR10R11)n−B−(CR10R11)l−
−(CR10R11)m−O−(CR10R11)n−
−(CR10R11)m−O−(CR10R11)n−B−(CR10R11)l−
−(CR10R11)n−B−(CR10R11)l−C(=O)−O−(CR10R11)m−
−(CR10R11)n−B−(CR10R11)l−O−(CR10R11)m−などが挙げられる。
一般式(24−1)で表される繰り返し単位(A)においてR9−1で表される酸不安定性基としては、下記一般式(d)〜(h)のいずれかで表される有機基が好ましい。
R13−O−CHR14− (e)
CR15R16R17− (f)
SiR15R16R17− (g)
R13−C(=O)− (h)
上述した一般式(d)〜(h)における、R13、R14、R15、R16およびR17は以下に説明する一価の有機基を表す。一般式(d)〜(h)のうち、(d)、(e)、(f)は光酸発生剤が受光して発生した酸(H+)により酸不安定性基が脱離すると共に酸を再生する機構を有する化学増幅型として機能するので、300nm以下の高エネルギー線で露光するパターン形成方法に適用するレジスト組成物として使用するのに特に好ましい。
中性ヒドロキシル基(「アルコール性ヒドロキシル基」ともいう。)は、ほぼ中性のヒドロキシル基であり、ベース樹脂に導入した場合、通常、アルカリ溶液への樹脂の溶解性を高める機能には関与せず、架橋剤との間でエステル結合、エーテル結合、ウレイド結合などのヒドロキシル基の関与する反応により架橋して、アルカリ水溶液に可溶であった樹脂成分を不溶または難溶性とする機能を有するヒドロキシル基をいう。
式中、W2は脂環式炭化水素基もしくは脂肪族炭化水素基またはこれらを組み合わせたh+1価の有機基を表し、hは1〜3の整数を表す。
繰り返し単位(C)としては、下に詳説する単量体の重合性二重結合が開裂して形成される繰り返し構造単位を挙げることができるが、これらに限定されるものではない。繰り返し単位(C)により、樹脂に要求される性能、特に、(1)塗布溶剤に対する溶解性、(2)製膜性(ガラス転移点)、(3)アルカリ現像性、(4)膜べり(親疎水性、アルカリ可溶性基選択)、(5)未露光部の基板への密着性、(6)ドライエッチング耐性、等の調整が可能となる。
ベース樹脂の重合方法としては、一般的に使用される方法であれば特に制限されないが、ラジカル重合、イオン重合などが好ましく、場合により、配位アニオン重合、リビングアニオン重合、カチオン重合、開環メタセシス重合、ビニレン重合、ビニルアディションなどを使用することも可能である。
本発明のレジスト組成物には、本発明の光酸発生剤と併せて公知の光酸発生剤を使用することができる。光酸発生剤としては、化学増幅型レジストの酸発生剤として用いられるものの中から、任意のものを選択して使用することができる。このような酸発生剤の例としては、ビススルホニルジアゾメタン類、ニトロベンジル誘導体類、オニウム塩類、ハロゲン含有トリアジン化合物類、シアノ基含有オキシムスルホネート化合物類、その他のオキシムスルホネート化合物などが挙げられる。これらの光酸発生剤の含有量は本発明の光酸発生剤と合わせてレジスト組成物100質量部に対して、通常0.5〜20質量部の範囲で選ばれる。この量が0.5質量部未満では像形成性が不十分であるし、20質量部を超えると均一な溶液が形成されにくく、保存安定性が低下する傾向がみられ好ましくない。また、光酸発生剤合計質量100質量部のうち本発明の光酸発生剤は1〜100質量部であり、10〜100質量部とするのが好ましく、30〜100質量部とするのがより好ましい。
本発明のレジスト組成物には、溶剤として有機溶媒を含む。使用する有機溶媒としては、含フッ素高分子化合物が可溶であれば特に制限されないが、アセトン、メチルエチルケトン、シクロヘキサノン、メチルイソアミルケトン、2‐ヘプタノンなどのケトン類やエチレングリコール、エチレングリコールモノアセテート、ジエチレングリコール、ジエチレングリコールモノアセテート、プロピレングリコール、プロピレングリコールモノアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、ジプロピレングリコール、又はジプロピレングリコールモノアセテートのモノメチルエーテル、モノエチルエーテル、モノプロピルエーテル、モノブチルエーテル又はモノフェニルエーテルなどの多価アルコール類及びその誘導体や、ジオキサンのような環式エーテル類や乳酸メチル、乳酸エチル、酢酸メチル、酢酸エチル、酢酸ブチル、ピルビン酸メチル、ピルビン酸エチル、メトキシプロピオン酸メチル、エトキシプロピオン酸エチルなどのエステル類、キシレン、トルエンなどの芳香族系溶媒、フロン、代替フロン、パーフルオロ化合物、ヘキサフルオロイソプロピルアルコールなどのフッ素系溶剤、塗布性を高める目的で高沸点弱溶剤であるターペン系の石油ナフサ溶媒やパラフィン系溶媒などが使用可能である。これらは単独で用いてもよいし、2種以上混合して用いてもよい。溶剤は、ベース樹脂などの固形分濃度が0.1〜10質量%である。具体的には、コーティング条件によりレジスト膜が10〜500μmとなるように濃度を調節して用いるが、通常、1〜5重量%程度である。
本発明のレジスト組成物には、クエンチャーとして、またはレジストパターン形状、引き置き経時安定性などを向上させるために、さらに任意の成分として、塩基性化合物を配合させることが好ましい。
ネガ型レジスト組成物の場合、化学増幅型のネガ型レジスト組成物に用いられている架橋剤として公知のものの中から任意に選択して用いることができる。
本発明のレジスト組成物は、界面活性剤、好ましくはフッ素系及び/又はシリコン系界面活性剤(フッ素系界面活性剤及びシリコン系界面活性剤、フッ素原子と珪素原子の両方を含有する界面活性剤)のいずれか、あるいは2種以上を含有することが好ましい。
本発明のレジスト組成物の使用方法は、従来のフォトレジスト技術のレジストパターン形成方法を用いることができる。すなわち、まずシリコンウエーハのような基板に、レジスト組成物の溶液をスピンナーなどを用いて塗布し、乾燥することによって感光層を形成させ、これに露光装置などにより高エネルギー線を所望のマスクパターンを介して照射し、加熱する。次いでこれを現像液、例えば0.1〜10質量%テトラメチルアンモニウムヒドロキシド水溶液のようなアルカリ性水溶液などを用いて現像処理する。この形成方法でマスクパターンに忠実なパターンを得ることができる。さらに、所望によってレジスト組成物に混和性のある添加物、例えば付加的樹脂、クエンチャー、可塑剤、安定剤、着色剤、界面活性剤、増粘剤、レベリング剤、消泡剤、相溶化剤、密着剤、酸化防止剤などの種々添加剤を含有させることができる。
1H NMR(測定溶媒:重クロロホルム,基準物質:テトラメチルシラン);δ=7.76−7.67(m,15H;Ph3S+),4.61(t,2H、J=16.0Hz), 4.26(q,2H,J=8.0Hz),2.00(m,3H,1−Ad),1.93(m,6H,1−Ad),1.69(m,6H,1−Ad).19F NMR(測定溶媒:重クロロホルム,基準物質:トリクロロフルオロメタン);δ=−79.0(s,3F),−115.7(m,2F)。
1H NMR(測定溶媒:重クロロホルム,基準物質:テトラメチルシラン);δ=7.69−7.62(m,15H;Ph3S+),4.16(q,2H,J=8.0Hz),4.00(m、2H),2.57(m、2H、),1.93(m,3H,1−Ad),1.82(m,6H,1−Ad),1.61(m,6H,1−Ad),1.27(t,3H,J=8.0Hz).19F NMR(測定溶媒:重クロロホルム,基準物質:トリクロロフルオロメタン);δ=−79.2(s,3F),−112.8(m,2F),−118.7(m,2F)。
1H NMR(測定溶媒:重クロロホルム,基準物質:テトラメチルシラン);δ=7.69−7.62(m,15H;Ph3S+),4.32(q,2H,J=8.0Hz),4.03(m、2H),2.24(m、2H、),1.95(m,3H,1−Ad),1.78(m,6H,1−Ad),1.61(m,6H,1−Ad),1.57(m、2H),1.43(m、2H),1.25(t,3H,J=8.0Hz).
19F NMR(測定溶媒:重クロロホルム,基準物質:トリクロロフルオロメタン);δ=−79.6(s,3F),−112.4(m,2F),−118.0(m,2F)。
<溶解度測定> 本発明の2−[1−エトキシカルボニル−1−(1−アダマンタン)カルボニルオキシ−2,2,2−トリフルオロエトキシ]−1,1−ジフルオロエタンスルホン酸トリフェニルスルホニル(PAG−1)、4−[1−エトキシカルボニル−1−(1-アダマンタン)カルボニルオキシ−2,2,2−トリフルオロエトキシ]−1,1,2,2−テトラフルオロブタンスルホン酸トリフェニルスルホニル(PAG−2)、または6−[1−エトキシカルボニル−1−(1−アダマンタン)カルボニルオキシ−2,2,2−トリフルオロエトキシ]−1,1,2,2−テトラフルオロヘキサンスルホン酸トリフェニルスルホニル(PAG−3)、そして既存の(1−アダマンチル)メトキシカルボニルジフルオロメタンスルホン酸トリフェニルスルホニル(PAG−C1)と2−(1−アダマンタン)カルボニルオキシ−1,1−ジフルオロエタンスルホン酸トリフェニルスルホニル(PAG−C2)の各種レジスト溶剤に対する溶解度を測定した。結果を表1に示す。
ろ別された白色粉末を二度400gのメタノールにてスラリー状で洗浄した後、ろ別し、50℃にて17時間乾燥し、白色粉末の重合体を得た(59.2g)。この重合体は質量平均分子量(MW)が7,600であり、13C−NMR分析の結果、化合物(A−1)由来の繰り返し単位:化合物(B−1)由来の繰り返し単位:化合物化合物(C−1)由来の繰り返し単位の含有比率が14.6:45.3:40.1(モル%)の共重合体であった。この共重合体を樹脂(P−1)とした。
重合例P−1と同様に樹脂(P−2〜P−8)を製造した。共重合に使用した単量体とその比率ならびに共重合後、各単量体から得られた繰り返し単位のモル比と質量平均分子量(MW)を表2に示した。
<レジスト組成物の調製と評価>
製造した各樹脂、溶剤およびその他の添加剤、並びに本発明の光酸発生剤(PAG)である2−[1−エトキシカルボニル−1−(1−アダマンタン)カルボニルオキシ−2,2,2−トリフルオロエトキシ]−1,1−ジフルオロエタンスルホン酸トリフェニルスルホニル(PAG−1)もしくは4−[1−エトキシカルボニル−1−(1-アダマンタン)カルボニルオキシ−2,2,2−トリフルオロエトキシ]−1,1,2,2−テトラフルオロブタンスルホン酸トリフェニルスルホニル(PAG−2)、6−[1−エトキシカルボニル−1−(1−アダマンタン)カルボニルオキシ−2,2,2−トリフルオロエトキシ]−1,1,2,2−テトラフルオロヘキサンスルホン酸トリフェニルスルホニル(PAG−3)または既存の光酸発生剤(PAG)である(1−アダマンチル)メトキシカルボニルジフルオロメタンスルホン酸トリフェニルスルホニル(PAG−C1)もしくは2−(1−アダマンタン)カルボニルオキシ−1,1−ジフルオロエタンスルホン酸トリフェニルスルホニル(PAG−C2)を配合してレジスト組成物を調合した。この時点で光酸発生剤(PAG)の溶解性を確認し、結果を表3に示した。
S−2:シクロヘキサノン
塩基性化合物:O−1:N,N−ジブチルアニリン
O−2:2,6−ジイソプロピルアニリン
O−3:ジアザビシクロ[4.3.0]ノネン
架橋剤:ニカラックMX−270(グリコールウリル系架橋剤、三和ケミカル製品)
次いで、各レジスト溶液をシリコンウェハー上にスピンコートし膜厚250nmのレジスト膜を得た。110℃でプリベークを行った後、フォトマスクを介して248nm紫外線での露光を行ったのち、120℃でポストエクスポーザーベークを行った。その後、2.38質量%テトラメチルアンモニウムヒドロキシド水溶液を用い、23℃で1分間現像した。比較例2を除き、パターニングしたいずれのレジスト組成物からも高解像のパターン形状が得られ、基板への密着不良欠陥、成膜不良欠陥、現像欠陥、エッチング耐性不良による欠陥は見られなかった。PAG−C1の場合、比較例8に示す様に特定の樹脂にを用いたときに限り、完全に溶解しかつ「きれいな矩形」のパターンが得られた。各レジストの組成及び評価結果を表3、表4に示す。
Claims (14)
- ベース樹脂、光酸発生剤及び溶剤を少なくとも含有してなるレジスト組成物において、光酸発生剤が、下記一般式(4)で表される含フッ素スルホン酸塩であるレジスト組成物。
(式中、Xはそれぞれ独立に水素原子またはフッ素原子を表す。nは1〜10の整数を表す。R1は水素原子、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基もしくはオキソアルキル基または炭素数6〜18のアリール基もしくはアラルキル基を表す。また、R 1 に含まれる炭素上の水素原子は、置換基によって置換されていてもよい。R2は、RAO、RBRCNのいずれかを表す。ここでRA、RBおよびRCは相互に独立に水素原子、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のオキソアルキル基、炭素数6〜18のアリール基、炭素数6〜18のアラルキル基、または炭素数3〜30のラクトン基を表す。RB及びRCは相互に結合してRBRCNの窒素原子(N)と共に環員数3〜18の複素環を形成していてもよい。また、RA、RBおよびRCに含まれる炭素上の水素原子は、置換基によって置換されていてもよい。Aは、
のうち何れか1つの基を表す。M+は一価のカチオンを表す。) - 光酸発生剤が、下記一般式(2)で表される含フッ素スルホン酸オニウム塩である請求項1に記載のレジスト組成物。
- 一般式(2)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜10の整数かつqが0〜8の整数である繰り返し単位を有する請求項2に記載のレジスト組成物。
- 一般式(2)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜4の整数かつqが0または1である繰り返し単位を有する請求項2または3に記載のレジスト組成物。
- ベース樹脂が、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル類、含フッ素ビニルエーテル類、アリルエーテル類、含フッ素アリルエーテル類、アクリルアミド類、メタクリルアミド類、ビニルエステル類、アリルエステル類、オレフィン類、含フッ素オレフィン類、ノルボルネン化合物および含フッ素ノルボルネン化合物からなる群より選ばれた一種の単量体を重合させた高分子重合体、又は、前記単量体の二種以上を共重合させた高分子共重合体であることを特徴とする、請求項2〜4の何れか1項に記載のレジスト組成物。
- ベース樹脂が、高エネルギー線露光前は現像液に不溶または難溶であって、露光後光酸発生剤の作用により現像液に可溶となる樹脂である請求項2〜5の何れか1項に記載のレジスト組成物。
- ベース樹脂が、高エネルギー線露光前は現像液に可溶であって、露光後光酸発生剤の作用により現像液に難溶または不溶となる樹脂である請求項2〜5の何れか1項に記載のレジスト組成物。
- 請求項1〜7の何れか1項に記載のレジスト組成物を基板上に塗布する工程と、加熱処理後フォトマスクを介して波長300nm以下の高エネルギー線で露光する工程と、必要に応じて加熱処理した後、現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
- 露光する工程が、波長193nmのArFエキシマレーザーを用い、レジスト組成物を塗布した基板と投影レンズの間に水、もしくは空気の屈折率より高い屈折率を有する水以外の液体を挿入する液浸リソグラフィ法であることを特徴とする請求項8に記載のパターン形成方法。
- 下記一般式(4)で表される含フッ素スルホン酸塩。
(式中、Xはそれぞれ独立に水素原子またはフッ素原子を表す。nは1〜10の整数を表す。R1は水素原子、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基もしくはオキソアルキル基または炭素数6〜18のアリール基もしくはアラルキル基を表す。また、R 1 に含まれる炭素上の水素原子は、置換基によって置換されていてもよい。R2は、RAO、RBRCNのいずれかを表す。ここでRA、RBおよびRCは相互に独立に水素原子、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のオキソアルキル基、炭素数6〜18のアリール基、炭素数6〜18のアラルキル基、または炭素数3〜30のラクトン基を表す。RB及びRCは相互に結合してRBRCNの窒素原子(N)と共に環員数3〜18の複素環を形成していてもよい。また、RA、RBおよびRCに含まれる炭素上の水素原子は、置換基によって置換されていてもよい。Aは、
のうち何れか1つの基を表す。M+は一価のカチオンを表す。)
- 含フッ素スルホン酸塩が下記一般式(2)で表される含フッ素スルホン酸オニウム塩である請求項10に記載の含フッ素スルホン酸塩。
(式中、X、n、A、R1およびR2は前記一般式(4)におけるX、n、A、R1およびR2とそれぞれ同義である。Q+は、下記一般式(a)で表されるスルホニウムカチオン、または下記一般式(b)で表されるヨードニウムカチオンを表す。)
(式中、R3、R4およびR5は、相互に独立に置換もしくは非置換の炭素数1〜20のアルキル基、アルケニル基もしくはオキソアルキル基、または置換もしくは非置換の炭素数6〜18のアリール基、アラルキル基もしくはアリールオキソアルキル基を表し、R3、R4およびR5のうちのいずれか2つ以上が相互に結合して式中の硫黄原子と共に環を形成してもよい。)
(式中、R6およびR7は、相互に独立に置換もしくは非置換の炭素数1〜20のアルキル基、アルケニル基もしくはオキソアルキル基、または置換もしくは非置換の炭素数6〜18のアリール基、アラルキル基もしくはアリールオキソアルキル基を表し、R6およびR7が相互に結合して式中のヨウ素原子と共に環を形成してもよい。)
- 一般式(4)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜10の整数かつqが0〜8の整数である繰り返し単位を有する請求項10に記載の含フッ素スルホン酸塩。
- 一般式(4)中、−(CX2) n −が、−(CH2)p−(CF2)q−で表され、pが0〜4の整数かつqが0または1である繰り返し単位を有する請求項10に記載の含フッ素スルホン酸塩。
- 請求項11に記載の含フッ素スルホン酸塩からなる光酸発生剤。
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TW201229018A (en) | 2012-07-16 |
KR101430057B1 (ko) | 2014-08-13 |
KR20130106409A (ko) | 2013-09-27 |
TWI449688B (zh) | 2014-08-21 |
WO2012056901A1 (ja) | 2012-05-03 |
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US20130209938A1 (en) | 2013-08-15 |
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