JP2011523971A - スルホニウム塩及び潜在性酸としての使用 - Google Patents

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Publication number

JP2011523971A

JP2011523971A JP2011512932A JP2011512932A JP2011523971A JP 2011523971 A JP2011523971 A JP 2011523971A JP 2011512932 A JP2011512932 A JP 2011512932A JP 2011512932 A JP2011512932 A JP 2011512932A JP 2011523971 A JP2011523971 A JP 2011523971A

Authority

JP

Japan

Prior art keywords

alkyl

interrupted

compound

formula

cycloalkyl

Prior art date

2008-06-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 239000002253 acid Substances 0.000 title claims abstract description 198
• 150000007513 acids Chemical class 0.000 title claims description 27
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title description 34
• -1 camphoryl Chemical group 0.000 claims abstract description 301
• 150000001875 compounds Chemical class 0.000 claims abstract description 214
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 107
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 88
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 58
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims abstract description 56
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 43
• 150000002367 halogens Chemical class 0.000 claims abstract description 43
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 42
• 239000001257 hydrogen Substances 0.000 claims abstract description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 39
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 24
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
• 229920000642 polymer Polymers 0.000 claims description 174
• 239000000203 mixture Substances 0.000 claims description 138
• 229920002120 photoresistant polymer Polymers 0.000 claims description 65
• 229920005989 resin Polymers 0.000 claims description 49
• 239000011347 resin Substances 0.000 claims description 49
• 238000000576 coating method Methods 0.000 claims description 46
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 38
• 239000000463 material Substances 0.000 claims description 37
• 230000009471 action Effects 0.000 claims description 33
• 125000004957 naphthylene group Chemical group 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 229910004013 NO 2 Inorganic materials 0.000 claims description 26
• 239000000758 substrate Substances 0.000 claims description 23
• 238000004519 manufacturing process Methods 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 239000004305 biphenyl Substances 0.000 claims description 19
• 235000010290 biphenyl Nutrition 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 17
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
• 238000007639 printing Methods 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 229910052786 argon Inorganic materials 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 239000000049 pigment Substances 0.000 claims description 13
• 239000000654 additive Substances 0.000 claims description 12
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000005549 heteroarylene group Chemical group 0.000 claims description 10
• 125000005561 phenanthryl group Chemical group 0.000 claims description 10
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 10
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 239000000976 ink Substances 0.000 claims description 6
• 125000006331 halo benzoyl group Chemical group 0.000 claims description 4
• 239000011159 matrix material Substances 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 2
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• 206010070834 Sensitisation Diseases 0.000 claims 1
• 125000004414 alkyl thio group Chemical group 0.000 claims 1
• 230000008313 sensitization Effects 0.000 claims 1
• 229920001577 copolymer Polymers 0.000 description 53
• 238000000034 method Methods 0.000 description 32
• 239000011248 coating agent Substances 0.000 description 31
• 238000006243 chemical reaction Methods 0.000 description 29
• 239000000178 monomer Substances 0.000 description 29
• 230000005855 radiation Effects 0.000 description 29
• 238000005516 engineering process Methods 0.000 description 28
• 238000002360 preparation method Methods 0.000 description 28
• 239000000243 solution Substances 0.000 description 25
• 239000010410 layer Substances 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 239000002904 solvent Substances 0.000 description 20
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 238000004090 dissolution Methods 0.000 description 18
• 239000010408 film Substances 0.000 description 18
• 125000004185 ester group Chemical group 0.000 description 17
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
• 238000004132 cross linking Methods 0.000 description 16
• JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 16
• 230000008569 process Effects 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
• 238000010894 electron beam technology Methods 0.000 description 15
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 15
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
• 239000011976 maleic acid Substances 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 229920003986 novolac Polymers 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 125000002950 monocyclic group Chemical group 0.000 description 12
• XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 11
• NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
• 238000001723 curing Methods 0.000 description 11
• 238000011161 development Methods 0.000 description 10
• 230000035945 sensitivity Effects 0.000 description 10
• 229920002554 vinyl polymer Polymers 0.000 description 10
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
• 239000003513 alkali Substances 0.000 description 9
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 230000003287 optical effect Effects 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
• 229920000877 Melamine resin Polymers 0.000 description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
• 239000003377 acid catalyst Substances 0.000 description 8
• 239000011230 binding agent Substances 0.000 description 8
• LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• 238000006116 polymerization reaction Methods 0.000 description 8
• 238000010526 radical polymerization reaction Methods 0.000 description 8
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
• 150000001241 acetals Chemical class 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 239000007859 condensation product Substances 0.000 description 7
• 239000000975 dye Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 230000007246 mechanism Effects 0.000 description 7
• 125000003367 polycyclic group Chemical group 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• DCTVCFJTKSQXED-UHFFFAOYSA-N (2-ethyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(CC)(OC(=O)C(C)=C)C2C3 DCTVCFJTKSQXED-UHFFFAOYSA-N 0.000 description 6
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 125000002947 alkylene group Chemical group 0.000 description 6
• 150000007514 bases Chemical class 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 6
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
• 238000005530 etching Methods 0.000 description 6
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 230000001678 irradiating effect Effects 0.000 description 6
• 238000001459 lithography Methods 0.000 description 6
• 150000002989 phenols Chemical class 0.000 description 6
• 229920001225 polyester resin Polymers 0.000 description 6
• 230000003595 spectral effect Effects 0.000 description 6
• 239000004094 surface-active agent Substances 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 229920000180 alkyd Polymers 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 239000012964 benzotriazole Substances 0.000 description 5
• 230000000903 blocking effect Effects 0.000 description 5
• 238000006555 catalytic reaction Methods 0.000 description 5
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• 238000003860 storage Methods 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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• AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• 239000004642 Polyimide Substances 0.000 description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
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• XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
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• 229940116333 ethyl lactate Drugs 0.000 description 4
• 125000001188 haloalkyl group Chemical group 0.000 description 4
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• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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• YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
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