KR102294584B1 - 치환된 아릴 오늄 물질 - Google Patents
치환된 아릴 오늄 물질 Download PDFInfo
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- KR102294584B1 KR102294584B1 KR1020140129438A KR20140129438A KR102294584B1 KR 102294584 B1 KR102294584 B1 KR 102294584B1 KR 1020140129438 A KR1020140129438 A KR 1020140129438A KR 20140129438 A KR20140129438 A KR 20140129438A KR 102294584 B1 KR102294584 B1 KR 102294584B1
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- 239000000463 material Substances 0.000 title description 9
- 125000003107 substituted aryl group Chemical group 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 88
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 230000005855 radiation Effects 0.000 claims description 19
- 150000001450 anions Chemical class 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000011247 coating layer Substances 0.000 claims description 15
- 150000007942 carboxylates Chemical class 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 230000003213 activating effect Effects 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910052740 iodine Chemical group 0.000 claims description 5
- 150000003871 sulfonates Chemical class 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 4
- 150000005690 diesters Chemical group 0.000 abstract description 11
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
- 229920000642 polymer Polymers 0.000 description 49
- 239000007787 solid Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 33
- 239000000178 monomer Substances 0.000 description 24
- -1 CH 2 (C=O)—O— Chemical class 0.000 description 23
- 239000010410 layer Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 150000002148 esters Chemical group 0.000 description 21
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 125000000129 anionic group Chemical group 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 125000000547 substituted alkyl group Chemical group 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000004404 heteroalkyl group Chemical group 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 235000012431 wafers Nutrition 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 235000009518 sodium iodide Nutrition 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 6
- BWBQPJBNCXDXHY-UHFFFAOYSA-M 4-O-(2-methyl-2-adamantyl) 1-O-[2-[(2-methyl-2-adamantyl)oxy]-2-oxoethyl] 2-(5-dibenzothiophen-5-ium-5-yl-2-methoxyphenyl)butanedioate chloride Chemical compound [Cl-].COc1ccc(cc1C(CC(=O)OC1(C)C2CC3CC(C2)CC1C3)C(=O)OCC(=O)OC1(C)C2CC3CC(C2)CC1C3)[S+]1c2ccccc2-c2ccccc12 BWBQPJBNCXDXHY-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 6
- 150000002596 lactones Chemical group 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 239000001301 oxygen Chemical group 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229940116333 ethyl lactate Drugs 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- DOZALMQRVQMIQK-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-(4-dibenzothiophen-5-ium-5-yl-2,6-dimethylphenoxy)acetate Chemical compound CC=1C=C([S+]2C3=CC=CC=C3C3=CC=CC=C32)C=C(C)C=1OCC(=O)OC1(CC)CCCC1 DOZALMQRVQMIQK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- QDFWCECOXXZMBN-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-chloroacetate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)CCl)C2C3 QDFWCECOXXZMBN-UHFFFAOYSA-N 0.000 description 3
- QSUJHKWXLIQKEY-UHFFFAOYSA-N (2-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCOC1=O QSUJHKWXLIQKEY-UHFFFAOYSA-N 0.000 description 3
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 3
- 0 *=C(CCOC(C(CC(C1)C2)(CC1C1)CC21O)=O)C(S(O)(=O)=O)=* Chemical compound *=C(CCOC(C(CC(C1)C2)(CC1C1)CC21O)=O)C(S(O)(=O)=O)=* 0.000 description 3
- IDNDBZMCTVQNCN-UHFFFAOYSA-M 1,1-difluoro-2-(2-methylprop-2-enoyloxy)ethanesulfonate Chemical compound CC(=C)C(=O)OCC(F)(F)S([O-])(=O)=O IDNDBZMCTVQNCN-UHFFFAOYSA-M 0.000 description 3
- CWIQIWPSCBKHTO-UHFFFAOYSA-M 1,1-difluoro-2-(2-methylprop-2-enoyloxy)ethanesulfonate;(1-ethylcyclopentyl) 2-(4-dibenzothiophen-5-ium-5-yl-2,6-dimethylphenoxy)acetate Chemical compound CC(=C)C(=O)OCC(F)(F)S([O-])(=O)=O.CC=1C=C([S+]2C3=CC=CC=C3C3=CC=CC=C32)C=C(C)C=1OCC(=O)OC1(CC)CCCC1 CWIQIWPSCBKHTO-UHFFFAOYSA-M 0.000 description 3
- CJEMFOYCRLPAEP-UHFFFAOYSA-N 2-(5-dibenzothiophen-5-ium-5-yl-2-methoxyphenyl)acetic acid iodide Chemical compound [I-].COc1ccc(cc1CC(O)=O)[S+]1c2ccccc2-c2ccccc12 CJEMFOYCRLPAEP-UHFFFAOYSA-N 0.000 description 3
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- PZIMFSLSQGQCPJ-UHFFFAOYSA-M [Cl-].CCC1(CCCC1)OC(=O)CC(C(=O)OCC(=O)OC1(C)C2CC3CC(C2)CC1C3)c1cc(ccc1OC)[S+]1c2ccccc2-c2ccccc12 Chemical compound [Cl-].CCC1(CCCC1)OC(=O)CC(C(=O)OCC(=O)OC1(C)C2CC3CC(C2)CC1C3)c1cc(ccc1OC)[S+]1c2ccccc2-c2ccccc12 PZIMFSLSQGQCPJ-UHFFFAOYSA-M 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000005156 substituted alkylene group Chemical group 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 3
- 150000008053 sultones Chemical class 0.000 description 3
- OZNXJXNWTDEPNB-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-chloroacetate Chemical compound ClCC(=O)OC1(CC)CCCC1 OZNXJXNWTDEPNB-UHFFFAOYSA-N 0.000 description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- SLIDVPRNQQFJNX-UHFFFAOYSA-N 2-[2-(5-dibenzothiophen-5-ium-5-yl-2-methoxyphenyl)acetyl]oxyacetic acid chloride Chemical compound [Cl-].COc1ccc(cc1CC(=O)OCC(O)=O)[S+]1c2ccccc2-c2ccccc12 SLIDVPRNQQFJNX-UHFFFAOYSA-N 0.000 description 2
- PPXAHQRRLKQYTG-UHFFFAOYSA-N 2-phenylpropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C1=CC=CC=C1 PPXAHQRRLKQYTG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NKYZCMARIDFISO-UHFFFAOYSA-N 4-O-(2-methyl-2-adamantyl) 1-O-[2-[(2-methyl-2-adamantyl)oxy]-2-oxoethyl] 2-(5-dibenzothiophen-5-ium-5-yl-2-methoxyphenyl)butanedioate Chemical compound COC1=C(C=C(C=C1)[S+]1C2=CC=CC=C2C2=C1C=CC=C2)C(CC(=O)OC1(C)C2CC3CC(C2)CC1C3)C(=O)OCC(=O)OC1(C)C2CC3CC(C2)CC1C3 NKYZCMARIDFISO-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- RHPMQCONVLOTCS-UHFFFAOYSA-M CC(=C)C(=O)OCC(F)(F)S([O-])(=O)=O.CC(C)(C)c1ccc(cc1)[S+]1c2ccccc2-c2ccccc12 Chemical compound CC(=C)C(=O)OCC(F)(F)S([O-])(=O)=O.CC(C)(C)c1ccc(cc1)[S+]1c2ccccc2-c2ccccc12 RHPMQCONVLOTCS-UHFFFAOYSA-M 0.000 description 2
- LXERXTXHJGISDQ-UHFFFAOYSA-M COC(CC(C=C(C=C1)[S+](C2=CC=CC=C22)C(C=CC=[C+]3)=C3C2=O)=C1OC)=O.[O-]S(C(F)(F)F)(=O)=O Chemical compound COC(CC(C=C(C=C1)[S+](C2=CC=CC=C22)C(C=CC=[C+]3)=C3C2=O)=C1OC)=O.[O-]S(C(F)(F)F)(=O)=O LXERXTXHJGISDQ-UHFFFAOYSA-M 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ICURIFUTRQEJPA-UHFFFAOYSA-N [3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CC(C(O)(C(F)(F)F)C(F)(F)F)CC(C(O)(C(F)(F)F)C(F)(F)F)C1 ICURIFUTRQEJPA-UHFFFAOYSA-N 0.000 description 2
- JHEWREKWELXDDH-UHFFFAOYSA-M [4-(2-methoxy-2-oxoethyl)naphthalen-1-yl]-diphenylsulfanium iodide Chemical compound [I-].COC(=O)Cc1ccc([S+](c2ccccc2)c2ccccc2)c2ccccc12 JHEWREKWELXDDH-UHFFFAOYSA-M 0.000 description 2
- QCGUWLDTIDPDIW-UHFFFAOYSA-N [Cl-].COc1ccc(cc1C(CC(O)=O)C(=O)OCC(O)=O)[S+]1c2ccccc2-c2ccccc12 Chemical compound [Cl-].COc1ccc(cc1C(CC(O)=O)C(=O)OCC(O)=O)[S+]1c2ccccc2-c2ccccc12 QCGUWLDTIDPDIW-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- BNQRSYFOIRGRKV-UHFFFAOYSA-N methyl 2-(2-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1OC BNQRSYFOIRGRKV-UHFFFAOYSA-N 0.000 description 1
- MWWVDNQGMOWFSK-UHFFFAOYSA-N methyl 2-ethoxypropaneperoxoate Chemical compound C(C)OC(C(=O)OOC)C MWWVDNQGMOWFSK-UHFFFAOYSA-N 0.000 description 1
- YGGXZTQSGNFKPJ-UHFFFAOYSA-N methyl 2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC=CC2=C1 YGGXZTQSGNFKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 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
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 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
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- 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
-
- 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
-
- 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
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- 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
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/040,587 | 2013-09-27 | ||
| US14/040,587 US10179778B2 (en) | 2013-09-27 | 2013-09-27 | Substituted aryl onium materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150035454A KR20150035454A (ko) | 2015-04-06 |
| KR102294584B1 true KR102294584B1 (ko) | 2021-08-26 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020140129438A Active KR102294584B1 (ko) | 2013-09-27 | 2014-09-26 | 치환된 아릴 오늄 물질 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10179778B2 (enExample) |
| JP (1) | JP6598445B2 (enExample) |
| KR (1) | KR102294584B1 (enExample) |
| CN (1) | CN104570602B (enExample) |
| TW (1) | TWI671283B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9304394B2 (en) * | 2013-09-27 | 2016-04-05 | Rohm And Haas Electronic Materials, Llc | Aryl acetate onium materials |
| US9606434B2 (en) * | 2014-10-10 | 2017-03-28 | Rohm And Haas Electronic Materials, Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
| US9551930B2 (en) | 2014-10-10 | 2017-01-24 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| KR101944290B1 (ko) | 2014-12-05 | 2019-04-17 | 도요 고세이 고교 가부시키가이샤 | 설폰산 유도체, 그것을 사용한 광산발생제, 레지스트 조성물 및 디바이스의 제조 방법 |
| JP7204343B2 (ja) | 2017-06-06 | 2023-01-16 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
| JP7556709B2 (ja) * | 2019-07-01 | 2024-09-26 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7618398B2 (ja) * | 2019-07-01 | 2025-01-21 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7556708B2 (ja) * | 2019-07-01 | 2024-09-26 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP2021008455A (ja) * | 2019-07-01 | 2021-01-28 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7627551B2 (ja) * | 2019-07-01 | 2025-02-06 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| US12140866B2 (en) | 2020-12-31 | 2024-11-12 | Rohm And Haas Electronic Materials Llc | Photoacid generators, photoresist compositions, and pattern formation methods |
| WO2025197401A1 (ja) * | 2024-03-22 | 2025-09-25 | Jsr株式会社 | 感放射線性組成物及びレジストパターン形成方法 |
| WO2025234401A1 (ja) * | 2024-05-08 | 2025-11-13 | Jsr株式会社 | 感放射線性組成物及びレジストパターン形成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004361577A (ja) * | 2003-06-03 | 2004-12-24 | Fuji Photo Film Co Ltd | 感光性組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287355A (en) | 1979-10-26 | 1981-09-01 | Sandoz, Inc. | Carboxyl-(phenyl or tolyl)-sulfonium salts |
| JPH11279213A (ja) * | 1998-03-30 | 1999-10-12 | Nippon Soda Co Ltd | オニウム塩化合物およびそれを含有する光硬化性組成物 |
| US7214465B2 (en) * | 2002-01-10 | 2007-05-08 | Fujifilm Corporation | Positive photosensitive composition |
| JP4083053B2 (ja) * | 2003-03-31 | 2008-04-30 | 富士フイルム株式会社 | ポジ型レジスト組成物 |
| JP2005274647A (ja) * | 2004-03-23 | 2005-10-06 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
| JP4866605B2 (ja) * | 2005-12-28 | 2012-02-01 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物を用いたパターン形成方法及び該感光性組成物に用いられる化合物 |
| JP2007293250A (ja) * | 2006-03-27 | 2007-11-08 | Fujifilm Corp | ポジ型レジスト組成物およびそれを用いたパターン形成方法 |
| WO2008056795A1 (en) * | 2006-11-10 | 2008-05-15 | Jsr Corporation | Polymerizable sulfonic acid onium salt and resin |
| TWI471298B (zh) | 2009-05-28 | 2015-02-01 | Sumitomo Chemical Co | 鹽及含有該鹽之光阻組成物 |
| JP5618877B2 (ja) | 2010-07-15 | 2014-11-05 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、新規な化合物及び酸発生剤 |
| JP5449276B2 (ja) * | 2011-09-02 | 2014-03-19 | 富士フイルム株式会社 | 感光性組成物に用いられる化合物 |
| TWI545118B (zh) | 2012-09-15 | 2016-08-11 | 羅門哈斯電子材料有限公司 | 酸產生劑化合物及包含該化合物之光阻劑 |
| JP6144164B2 (ja) | 2012-09-15 | 2017-06-07 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | オニウム化合物およびその合成方法 |
| US9304394B2 (en) * | 2013-09-27 | 2016-04-05 | Rohm And Haas Electronic Materials, Llc | Aryl acetate onium materials |
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- 2014-09-26 JP JP2014197477A patent/JP6598445B2/ja active Active
- 2014-09-26 KR KR1020140129438A patent/KR102294584B1/ko active Active
- 2014-09-29 CN CN201410755977.4A patent/CN104570602B/zh active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004361577A (ja) * | 2003-06-03 | 2004-12-24 | Fuji Photo Film Co Ltd | 感光性組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US10179778B2 (en) | 2019-01-15 |
| TWI671283B (zh) | 2019-09-11 |
| CN104570602B (zh) | 2019-12-10 |
| JP2015091935A (ja) | 2015-05-14 |
| JP6598445B2 (ja) | 2019-10-30 |
| TW201524947A (zh) | 2015-07-01 |
| US20150093708A1 (en) | 2015-04-02 |
| CN104570602A (zh) | 2015-04-29 |
| KR20150035454A (ko) | 2015-04-06 |
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