WO2001068575A1 - Cation de type sel de fluoroalkylonium ou generateur d'acides generant des cations ou des acides lorsqu'il est irradie par des rayons d'energie - Google Patents
Cation de type sel de fluoroalkylonium ou generateur d'acides generant des cations ou des acides lorsqu'il est irradie par des rayons d'energie Download PDFInfo
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- WO2001068575A1 WO2001068575A1 PCT/JP2001/001060 JP0101060W WO0168575A1 WO 2001068575 A1 WO2001068575 A1 WO 2001068575A1 JP 0101060 W JP0101060 W JP 0101060W WO 0168575 A1 WO0168575 A1 WO 0168575A1
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- WIPO (PCT)
- Prior art keywords
- group
- carbon atoms
- aryl
- alkyl
- atom
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- 239000002253 acid Substances 0.000 title claims abstract description 79
- 150000001768 cations Chemical class 0.000 title claims abstract description 53
- 150000003839 salts Chemical class 0.000 title claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011593 sulfur Substances 0.000 claims abstract description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 13
- 239000011574 phosphorus Substances 0.000 claims abstract description 13
- 229910052714 tellurium Inorganic materials 0.000 claims abstract description 13
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011669 selenium Substances 0.000 claims abstract description 12
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 11
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- -1 salt cation Chemical class 0.000 claims description 27
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- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
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- 125000004104 aryloxy group Chemical group 0.000 claims description 7
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- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- 125000004434 sulfur atom Chemical group 0.000 claims description 6
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- 125000006551 perfluoro alkylene group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
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- 239000003795 chemical substances by application Substances 0.000 claims description 2
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- 241001024304 Mino Species 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract description 10
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
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- 210000000349 chromosome Anatomy 0.000 description 1
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- RDFLLVCQYHQOBU-ZOTFFYTFSA-O cyanin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=[O+]C1=CC(O)=C2)C=3C=C(O)C(O)=CC=3)=CC1=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 RDFLLVCQYHQOBU-ZOTFFYTFSA-O 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
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- CGDXUTMWWHKMOE-UHFFFAOYSA-N difluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)F CGDXUTMWWHKMOE-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- KDEZIUOWTXJEJK-UHFFFAOYSA-N heptacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C21 KDEZIUOWTXJEJK-UHFFFAOYSA-N 0.000 description 1
- QSQIGGCOCHABAP-UHFFFAOYSA-N hexacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C21 QSQIGGCOCHABAP-UHFFFAOYSA-N 0.000 description 1
- OQLKNTOKMBVBKV-UHFFFAOYSA-N hexamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCCOC1=CC=C(C(N)=N)C=C1 OQLKNTOKMBVBKV-UHFFFAOYSA-N 0.000 description 1
- 229960001915 hexamidine Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 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
- 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
- BBDGYADAMYMJNO-UHFFFAOYSA-N n-butyl-n-ethylbutan-1-amine Chemical compound CCCCN(CC)CCCC BBDGYADAMYMJNO-UHFFFAOYSA-N 0.000 description 1
- ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 1
- ZBZSKMOKRUBBGC-UHFFFAOYSA-N n-ethyl-n-hexylhexan-1-amine Chemical compound CCCCCCN(CC)CCCCCC ZBZSKMOKRUBBGC-UHFFFAOYSA-N 0.000 description 1
- BXYHQXUPLKMYDE-UHFFFAOYSA-N n-heptyl-n-methylheptan-1-amine Chemical compound CCCCCCCN(C)CCCCCCC BXYHQXUPLKMYDE-UHFFFAOYSA-N 0.000 description 1
- POMGZMHIXYRARC-UHFFFAOYSA-N n-hexyl-n-methylhexan-1-amine Chemical compound CCCCCCN(C)CCCCCC POMGZMHIXYRARC-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- IITLRKXIQJEWFI-UHFFFAOYSA-N n-methyl-n-nonylnonan-1-amine Chemical compound CCCCCCCCCN(C)CCCCCCCCC IITLRKXIQJEWFI-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 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
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical group FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- 150000003643 triphenylenes Chemical class 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/64—Quaternary ammonium compounds having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
- C07C25/13—Monocyclic aromatic halogenated hydrocarbons containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C395/00—Compounds containing tellurium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
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- 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
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
-
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- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- 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
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5449—Polyphosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to fluorinated cations or acid generators which generate cations or acids upon irradiation with energy rays. . Background art
- phosporium salts such as slumps and rhododiums have been exposed to actinic rays (e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.) in the present specification. It is widely known that it absorbs and decomposes to generate a strong acid.
- actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
- actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
- actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
- actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
- the present inventors have developed a high sensitivity that can improve the above performance.
- Investigation of the acid generator of the present invention led to the discovery of a fluoroalkyl oxonium salt into which a fluoroalkyl group was introduced. Therefore, the purpose of the present invention is to produce cations or acid generators that are denatured by energy rays in fields such as photo resist.
- An object of the present invention is to provide a compound which is effective as an agent and a chemically amplified resist material obtained by combining the compound. Disclosure of the invention
- the above-mentioned problem of the present invention is to generate a cation or an acid by irradiation with energy, the formula (1):
- A is an element selected from iodine, sulfur, selenium, tellurium, nitrogen or phosphorus;
- R 2 and R 3 are absent, and R 1 is an alkyl group having 15 carbon atoms or a aryl group having 6 to 15 carbon atoms. ;
- R 3 When A is sulfur, selenium or tellurium, R 3 is absent, and R and R 2 are each independently an alkyl group having 1 to 15 carbon atoms.
- C7-C35 alkylalylamino group Is a diarylamino group having 12 to 40 carbon atoms, and shaku 1 and R 2 may be mutually bonded to form a ring;
- R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 15 carbon atoms, 6 to 20 aryl groups, 2 to 30 dialkylamino groups, carbon number? 1-3 5
- a Le kills ⁇ rie was Le A Mi amino group or of Ri Oh di ⁇ Re Ichiru ⁇ Mi amino group having 1 2-4 0 carbon atoms, R 1 and R 2 and R 3 each each other May form one or more rings, or R 3 may be absent, and R 1 and R 2 may combine to form an aromatic ring containing A.
- I is an alkyl group having 1 to 15 carbon atoms, 6 to 20 aryl groups, 2 to 30 dialkylamino groups, carbon number? 1-3 5
- a Le kills ⁇ rie was Le A Mi amino group or of Ri Oh di ⁇ Re Ichiru ⁇ Mi amino group having 1 2-4 0 carbon atoms, R 1 and R 2 and R 3 each each other May form one or more rings, or R 3 may be absent, and R 1 and R 2 may combine
- the aryl group, the alkyl group of the alkyl aryl group and the aryl group of the aryl amino group may be Alkyl group, octaalkyl group, halogen atom, alkoxy group, aryloxy group, nitro group, amide group, cyano group, alkanol group, It may be substituted with an arylyl group, an alkoxycarbonyl group, an aryloxycarbonyl group or an acyloxy group; R f is branched. Or a perfluoroalkyl group having 1 to 15 carbon atoms which may form a ring. A part of the fluorine of the fluoroalkyl group has been replaced with hydrogen;
- X — is the conjugate base of Brentsted acid) or
- R 5 X 1 R 8 (In the formula, A 1 and A 2 are the same or different, and each is an element selected from iodine, sulfur, selenium, tellurium, nitrogen, or phosphorus. Yes;
- R 5 and R 8 are absent, and R 4 and R 7 are each independently a carbon atom of 1 to Alkyl group with 15 alkyl groups, aryl group with 6 to 20 carbon atoms, dialkylamino group with 2 to 30 carbon atoms, and alkyl library with 7 to 35 carbon atoms A ruamino group or a diarylamino group having 12 to 40 carbon atoms;
- R 4 , R 5 , R 7 and R 8 are each independently an alkyl having 1 to 15 carbon atoms.
- the above-mentioned alkyl group, the alkyl group of the dialkylamino group and the alkyl group of the alkylaryl amino group are an aryl group, a halogen group. It may be substituted by a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, or a silicon atom, may be branched, may form a ring,
- the aryl group, the alkyl group and the aryl group of the aryl and amino groups are the alkyl group, the alkyl group and the alkyl group.
- R 6 is an aryl group, a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom or a silicon atom.
- R f may be a branched or may form a ring, a perfluoroalkyl group having 1 to 15 carbon atoms, or a perylfluoroalkyl group A part of the fluorine of the above has been replaced by hydrogen;
- X — is a conjugate base of brentsted acid), and relates to a cation or an acid generator in the form of a fluoroalkylonium salt represented by the formula:
- R f in the above formula (1) or (2) _CH 2 R f 1 (R f 1 may be branched or may form a ring.
- R f 2 CF 2 H R f 2 is a perfluoroalkylene group having 1 to 14 carbon atoms, which may be branched or form a ring.
- Fluoroalkylene groups in which some of the fluorine in the fluoroalkylene group has been replaced with hydrogen or _CH 2 R f 3 CF 2 H (R f 3 is branched and A perfluoroalkylene group having 1 to 13 carbon atoms, which may form a ring, or a part of the fluorine of the perfluoroalkylene group is preferred. It has been replaced with hydrogen ), And X_ is preferably a conjugated base of fluoroalkylsulfonate.
- Fluoroalkylene salt of the present invention Salt-type cation or acid generator is converted to a negative-type resist resin or a positive-type resist. By blending it with resin, highly sensitive chemically amplified resist materials can be manufactured. Best mode for carrying out the invention In general, the cation or acid generator binds to the core element A and to it by the irradiated energy. One of the moieties (substituents) is cut off, and the cut-off substituent becomes a cation or the anion removes a hydrogen atom to become an acid group. This generates cations or acids (J. Po1 ym. Sci. Part A: Po1 ym. Chem. 30, 23 65-23) 6 9 (1992); Macromo 1 ecu 1 es, 24, 2 13 7-2 13 9 (1 9 9)).
- the core element A has higher cationicity and higher reactivity than the acid generators. However, it can be a cation generator or an acid generator with much higher sensitivity to energy rays.
- the substituent constant (am) of the Hammett of each substituent was-0.06 for the methyl group, 0.04 for the phenyl group, and 10 for the benzyl group.
- the trifluoromethyl group is 0.46 (edited by The Chemical Society of Japan,
- fluoroalkylonium salts are used in the field of synthetic organic chemistry to introduce fluoroalkyl groups into various organic compounds. It has only been disclosed as a test reagent.
- A is For sulfur, selenium or tellurium, where R 1 is an alkyl group or an aryl group and R 2 is an aryl group, Zh.Org. , 15, 2432 (1979), and J. Org. Chem. USSR, 15, 222 (1977).
- R f and have contact to or formula (1) is - if CH a R f 1 Ah Ru in, A is also R f 1 group in sulfur Ru Ah with CF 3, in R 1, R 2 co It has been reported that the synthesis of a methyl group, a phenyl group together, and a phenyl group bonded to form a ring are also possible. (Bull. Chem. Soc. Jpn. 64, 2008 (1991)). In the formula (1), when A is sulfur and R 1 and R 2 are both a dialkylamino group, Chem. Ber., 124, 31 ( 1 9 9 1).
- fluoroalkionium salts that can be used in the present invention, but are not limited to these but are examples.
- fluoroalkyronedium salts described in the above-mentioned documents can also be used.
- X in the fluoroalkionium salt used in the present invention is a synergistic base for blended acid.
- prested acid include trifluorene sulfonic acid, tetrafluorene sulfonic acid, and perfluorinated acid.
- fluoroalkylsulfuric acid such as sulfonic acid, difluoromethansulfonate, etc., methansulfonic acid, and Chromosome sunsulphonic acid, benzenesulphonic acid, toluenesulphonic acid, sulfuric acid, fluorosulphonic acid, chlorosurul Ho phosphate, HBF 4, HS b F 6 , HPF 6, HS b C l 5 F, HS b C l 6, HA s F 6, HBC 1 3 F, HA 1 C 1 4 , etc.
- Re is Ah up al But is limited to this is not .
- fluoroalkyl sulfonate is preferred because it is a strong acid and does not generate hydrogen fluoride or hydrogen chloride.
- the cation or acid generator of the present invention basically consists of the above-mentioned fluoroalkyl sulfonium salt, but if necessary, other cations or acid generators may be used. A known cation or acid generator may be used in combination.
- the cations or acid generators of the present invention are highly sensitive to these energy lines, and are less than conventional acid generators. A large amount of radiation can produce cations or acids.
- the fluoroalkionium salt of the present invention salt-type cations or acid generators can be combined with sensitizers to produce The activity against the glow is further enhanced, and it can be used as an ultra-sensitive cation or acid generator.
- the sensitizer include naphthene-lens conductor, enthracene-induced conductor, phenanthrene-induced conductor, pyrene-induced conductor, naphthene-induced conductor, and Condensed polycyclic aromatic conductors, such as relene conductors, pentyne conductors, hexacene conductors, heptacene conductors, etc., fluorene conductors, na Footquinone dielectric, anthraquinone dielectric, benzoin dielectric, xanthen dielectric, thioxanthen dielectric, xanthen dielectric , Chixanthon dielectric, coumalin dielectric, cyanin dielectric, melocyan
- the cations or acid generators of the present invention are energy-line It can generate cations or acids by irradiation, and can be used in fields where the generated cations or acids are used.
- a chemically amplified type that converts a resin containing a functional group into a soluble or insoluble form in a developer by using the generated cation or acid as a catalyst. It is useful as a cation or acid generator for resist materials.
- the cation or acid generator of the present invention is formed by crosslinking or condensing the cation or acid generated as a resist resin with a developer or a developer. If a resin of a type that is insoluble in water is used, it becomes a chemically amplified negative resist material.
- resist resins include, for example, cyclized isoprene-based negative resists and polyvinyl alcohol-based negative resists. Polyvinyl citrate-based negative resists, copolymers of polyester acrylate and hydroxystyrene, and the like. It is.
- the resist resin is, for example, an alkali-soluble resin serving as a base resin, such as a nopolak resin; Enol resin; Polyisopropionyl phenol resin; Vinyl phenol and acrylic acid, methacrylic acid, acrylonitrile Lilyl, methyl methacrylate, methylyl acrylate, maleic acid, maleic anhydride, isopropenyl phenol, Copolymer with styrene or ⁇ -methylstyrene; isopropenyl phenol and acrylic acid, methacrylic acid, ac Rilonitrile, methyl methacrylate, methyl acrylate, maleic acid, anhydrous maleic acid, isopro ⁇ Nil phenol, steel
- the positional relationship between the hydroxyl group and vinyl or isoprol group Is not particularly limited, but in general, P—vinylphenol or P—isopronylphenol is preferred.
- These resins may be partially hydrogenated to improve the transparency.
- an alkyl group, a hydroxyl group, etc. may be introduced into the phenol nucleus of the resin within a range that is soluble in the alkali.
- polyvinyl phenol resin that is, a single polymer or vinyl phenol resin, is used. Copolymers of vinyl phenol with other monomers are preferred.
- a group which is introduced into an alkali-soluble resin has a dissolution inhibiting property in an alkaline developer but is unstable to an acid
- various known groups can be used.
- Protecting groups can be employed. For example, tert—butoxycarbonyl, tert—butoxymethyl, 11-ethoxy, 1-methoxy , 1 _ Propoxethyl, 1-Isoproxethyl, 1 tert-Butoxycil, 1-Isobutoxylile, 1 _ Bu Tokichiru, 1-punch opening kit, 1-kro opening opening kit, 1_tok opening, 1-k opening Mouth mouth mouth, 1 — mouth mouth mouth, 1 — Cyclo mouth mouth, 1 mouthpiece or 1-medium Toxicity 11 Alkoxyalkyl groups such as methylethyl; tetrahydro 2-vinylanil, 6-methoxy Lahidlow 2 Vilanil, 6—Extra-Hydroxy 2—Vila Nile, Tetra-Hydrogen 2—
- the cation or acid generator of the present invention is highly sensitive to energy rays.
- the addition amount of cation or acid generator may be smaller than in the past.
- 0.1 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, with respect to 100 parts by weight of the resist resin is preferable.
- the above-mentioned other acid generator and Z or a sensitizer may be used in combination.
- an organic base compound is added as a quencher. It is known that the performance deterioration due to the deactivation of the acid due to the post-exposure pull-in can be improved, and this is also the case with the present invention. It is preferable to add an organic base compound.
- the organic base compounds used herein include, for example, hexylamine, heptylamine, octylamine, nonylamine, and decylamine.
- tertiary amides such as N, N-dimethylmethylanilinine; ethylenediamine, tetramethylenediamine or hexamidine; Diamines such as thiresamine; imidazole, pyridin, 4-methylpyridin, 4—methylimidazole or bipyridin; Unsaturated cyclic amines such as gin are produced. These organic base compounds can be used alone or in combination of two or more.
- the degree of decomposition was determined by measuring 19 F-NMR.
- the solution was transferred to a sample bottle using 1 ml of acetonitrile, and 8 ml of pure water was stirred with stirring, and one minute later, the pH was measured.
- the measurement of the PH of the solution was started using the method, and the measurement was performed three times within two minutes, and the average value was obtained. Table 1 shows the results.
- the fluoroalkylonium salt used in the present invention can be prepared by any of the various methods described in the above-mentioned known documents, or a combination of the various methods with various organic chemical methods. It can be synthesized in a new way.
- Example 46 the fluoroalkyl kilonium salt synthesized in Example 46 is a novel compound.
- the present invention it is possible to provide a cation or an acid generator with high sensitivity to energy rays.
- this cation or acid generator is blended into the resist resin, the irradiation time of the energy beam can be reduced, thus shortening the irradiation time.
- the resist processing can be performed only by irradiating high energy rays for a very short time, so that ultra-fine processing can be achieved.
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Abstract
La présente invention concerne un générateur de cations ou d'acides qui, lorsqu'il est irradié par des rayons d'énergie, peut générer des cations ou des acides à haute sensibilité. Ce générateur peut être particulièrement utilisé dans des matériaux de réserve de type à amplification chimique. Il comprend un sel de fluoroalkylonium sensible au rayons d'énergie, représenté par la formule (1), dans laquelle R1 à R3 (représentant chacun alkyle, aryle, etc.) et R¿f? (fluoroalkyle) sont liés à l'élément central A (iode, soufre, sélénium, tellure, azote, ou phosphore). En outre, cette invention concerne un matériau de réserve de type à amplification chimique contenant un générateur d'acides.
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JP2000068241A JP2001255647A (ja) | 2000-03-13 | 2000-03-13 | エネルギー線照射によりカチオンまたは酸を発生するフルオロアルキルオニウム塩型のカチオンまたは酸発生剤 |
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WO2002039186A2 (fr) * | 2000-11-09 | 2002-05-16 | E. I. Du Pont De Nemours And Company | Generateurs photoacides utilises dans des compositions de photoresist pour la microlithographie |
WO2003040090A1 (fr) * | 2001-11-06 | 2003-05-15 | Wako Pure Chemical Industries, Ltd. | Sel onium hybride |
JP2004233661A (ja) * | 2003-01-30 | 2004-08-19 | Fuji Photo Film Co Ltd | 感刺激性組成物及び化合物 |
JP2009040761A (ja) * | 2007-07-18 | 2009-02-26 | Tokyo Ohka Kogyo Co Ltd | 新規な化合物およびその製造方法、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
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JP5366075B2 (ja) * | 2008-11-18 | 2013-12-11 | 国立大学法人 名古屋工業大学 | トリフルオロメチルチオフェニウム誘導体塩、その製造方法、その中間体並びにそれを用いたトリフルオロメチル基含有化合物類の製造方法 |
US8338076B2 (en) | 2008-11-28 | 2012-12-25 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, novel compound, and acid generator |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS612702A (ja) * | 1984-06-15 | 1986-01-08 | Toyo Soda Mfg Co Ltd | パ−フルオロアルキル基含有重合体の製造方法 |
GB2273927A (en) * | 1992-12-09 | 1994-07-06 | Du Pont | Sensitized onium salts |
JPH10182824A (ja) * | 1996-12-27 | 1998-07-07 | Kagaku Gijutsu Shinko Jigyodan | ポリ(アリーレンスルホニウム塩)化合物 |
EP0869393A1 (fr) * | 1997-03-31 | 1998-10-07 | Fuji Photo Film Co., Ltd. | Composition photosensible travaillant en positif |
JPH1152562A (ja) * | 1997-08-08 | 1999-02-26 | Sumitomo Chem Co Ltd | フォトレジスト組成物 |
JPH11305440A (ja) * | 1998-04-23 | 1999-11-05 | Tokyo Ohka Kogyo Co Ltd | レジストパターンの形成方法 |
-
2000
- 2000-03-13 JP JP2000068241A patent/JP2001255647A/ja active Pending
-
2001
- 2001-02-15 WO PCT/JP2001/001060 patent/WO2001068575A1/fr active Application Filing
- 2001-02-27 TW TW90104491A patent/TW574184B/zh active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS612702A (ja) * | 1984-06-15 | 1986-01-08 | Toyo Soda Mfg Co Ltd | パ−フルオロアルキル基含有重合体の製造方法 |
GB2273927A (en) * | 1992-12-09 | 1994-07-06 | Du Pont | Sensitized onium salts |
JPH10182824A (ja) * | 1996-12-27 | 1998-07-07 | Kagaku Gijutsu Shinko Jigyodan | ポリ(アリーレンスルホニウム塩)化合物 |
EP0869393A1 (fr) * | 1997-03-31 | 1998-10-07 | Fuji Photo Film Co., Ltd. | Composition photosensible travaillant en positif |
JPH1152562A (ja) * | 1997-08-08 | 1999-02-26 | Sumitomo Chem Co Ltd | フォトレジスト組成物 |
JPH11305440A (ja) * | 1998-04-23 | 1999-11-05 | Tokyo Ohka Kogyo Co Ltd | レジストパターンの形成方法 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002039186A2 (fr) * | 2000-11-09 | 2002-05-16 | E. I. Du Pont De Nemours And Company | Generateurs photoacides utilises dans des compositions de photoresist pour la microlithographie |
WO2002039186A3 (fr) * | 2000-11-09 | 2002-11-21 | Du Pont | Generateurs photoacides utilises dans des compositions de photoresist pour la microlithographie |
WO2003040090A1 (fr) * | 2001-11-06 | 2003-05-15 | Wako Pure Chemical Industries, Ltd. | Sel onium hybride |
CN100418947C (zh) * | 2001-11-06 | 2008-09-17 | 和光纯药工业株式会社 | 杂化鎓盐 |
KR100902374B1 (ko) * | 2001-11-06 | 2009-06-11 | 와코 쥰야꾸 고교 가부시키가이샤 | 하이브리드형 오늄염 |
JP2004233661A (ja) * | 2003-01-30 | 2004-08-19 | Fuji Photo Film Co Ltd | 感刺激性組成物及び化合物 |
JP2009040761A (ja) * | 2007-07-18 | 2009-02-26 | Tokyo Ohka Kogyo Co Ltd | 新規な化合物およびその製造方法、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
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