JP4489954B2 - 新規な不飽和オキシム誘導体及び潜在的な酸としてのその用途 - Google Patents

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Publication number

JP4489954B2

JP4489954B2 JP2000566246A JP2000566246A JP4489954B2 JP 4489954 B2 JP4489954 B2 JP 4489954B2 JP 2000566246 A JP2000566246 A JP 2000566246A JP 2000566246 A JP2000566246 A JP 2000566246A JP 4489954 B2 JP4489954 B2 JP 4489954B2

Authority

JP

Japan

Prior art keywords

phenyl

alkyl

substituted

unsubstituted

acid

Prior art date

1998-08-19

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.)

Expired - Fee Related

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• 239000002253 acid Substances 0.000 title claims description 80
• 150000002923 oximes Chemical class 0.000 title description 15
• 150000007513 acids Chemical class 0.000 title description 4
• -1 anthracyl Chemical group 0.000 claims description 208
• 239000000203 mixture Substances 0.000 claims description 101
• 125000000217 alkyl group Chemical group 0.000 claims description 81
• 150000001875 compounds Chemical class 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 238000000576 coating method Methods 0.000 claims description 47
• 229920002120 photoresistant polymer Polymers 0.000 claims description 35
• 239000011248 coating agent Substances 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 239000000463 material Substances 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
• 229920000642 polymer Polymers 0.000 claims description 23
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 238000004132 cross linking Methods 0.000 claims description 17
• 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 17
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000004957 naphthylene group Chemical group 0.000 claims description 14
• IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 12
• 125000001589 carboacyl group Chemical group 0.000 claims description 12
• 238000007639 printing Methods 0.000 claims description 12
• 125000005561 phenanthryl group Chemical group 0.000 claims description 11
• 230000009471 action Effects 0.000 claims description 10
• 239000000654 additive Substances 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 8
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
• 239000000976 ink Substances 0.000 claims description 6
• 230000001678 irradiating effect Effects 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
• 125000006331 halo benzoyl group Chemical group 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
• 235000010290 biphenyl Nutrition 0.000 claims 1
• 239000004305 biphenyl Substances 0.000 claims 1
• 125000006267 biphenyl group Chemical group 0.000 claims 1
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 23
• 229920005989 resin Polymers 0.000 description 23
• 239000011347 resin Substances 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 125000003545 alkoxy group Chemical group 0.000 description 19
• 230000005855 radiation Effects 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000011230 binding agent Substances 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• 239000000243 solution Substances 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• 238000001723 curing Methods 0.000 description 12
• 238000002844 melting Methods 0.000 description 12
• 230000008018 melting Effects 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000000049 pigment Substances 0.000 description 12
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
• 238000004090 dissolution Methods 0.000 description 11
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 238000011161 development Methods 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
• 239000000178 monomer Substances 0.000 description 9
• 239000000758 substrate Substances 0.000 description 9
• 229920000877 Melamine resin Polymers 0.000 description 8
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 239000010408 film Substances 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 229920000178 Acrylic resin Polymers 0.000 description 7
• 238000007171 acid catalysis Methods 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 239000003086 colorant Substances 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 229920001225 polyester resin Polymers 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
• SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 239000012043 crude product Substances 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 239000004922 lacquer Substances 0.000 description 6
• RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
• QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
• IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• 230000035945 sensitivity Effects 0.000 description 6
• 235000010288 sodium nitrite Nutrition 0.000 description 6
• WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
• FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 5
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
• 150000001241 acetals Chemical class 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 229920000180 alkyd Polymers 0.000 description 5
• 229920003180 amino resin Polymers 0.000 description 5
• 239000000975 dye Substances 0.000 description 5
• 238000000921 elemental analysis Methods 0.000 description 5
• 239000005457 ice water Substances 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 230000007246 mechanism Effects 0.000 description 5
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
• BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 5
• 230000007935 neutral effect Effects 0.000 description 5
• 239000005011 phenolic resin Substances 0.000 description 5
• 150000002989 phenols Chemical class 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 4
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
• 239000003513 alkali Substances 0.000 description 4
• 235000010233 benzoic acid Nutrition 0.000 description 4
• 239000004202 carbamide Substances 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• 239000004611 light stabiliser Substances 0.000 description 4
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
• 229910052753 mercury Inorganic materials 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 229920003986 novolac Polymers 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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• 238000000746 purification Methods 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
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• 239000000080 wetting agent Substances 0.000 description 4
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 3
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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• 229910004298 SiO 2 Inorganic materials 0.000 description 3
• NLNBTAIZGBAQQQ-UHFFFAOYSA-N [(1-cyano-2-methyl-3-phenylprop-2-enylidene)amino] methanesulfonate Chemical compound CS(=O)(=O)ON=C(C#N)C(C)=CC1=CC=CC=C1 NLNBTAIZGBAQQQ-UHFFFAOYSA-N 0.000 description 3
• UTCGTYIQPXXZSN-UHFFFAOYSA-N [(1-cyano-2-oxo-4-phenylbut-3-enylidene)amino] methanesulfonate Chemical compound CS(=O)(=O)ON=C(C#N)C(=O)C=CC1=CC=CC=C1 UTCGTYIQPXXZSN-UHFFFAOYSA-N 0.000 description 3
• YQZJEMNKTURAOV-UHFFFAOYSA-N [[1-cyano-3-(4-methoxyphenyl)prop-2-enylidene]amino] methanesulfonate Chemical compound COC1=CC=C(C=CC(=NOS(C)(=O)=O)C#N)C=C1 YQZJEMNKTURAOV-UHFFFAOYSA-N 0.000 description 3
• IUPQXSCDILAWBZ-UHFFFAOYSA-N [[1-cyano-3-(4-methylphenyl)prop-2-enylidene]amino] methanesulfonate Chemical compound CC1=CC=C(C=CC(=NOS(C)(=O)=O)C#N)C=C1 IUPQXSCDILAWBZ-UHFFFAOYSA-N 0.000 description 3
• HLPNGVWWQPWYDF-UHFFFAOYSA-N [[1-cyano-3-[4-[[4-(3-cyano-3-methylsulfonyloxyiminoprop-1-enyl)phenyl]methyl]phenyl]prop-2-enylidene]amino] methanesulfonate Chemical compound C1=CC(C=CC(=NOS(=O)(=O)C)C#N)=CC=C1CC1=CC=C(C=CC(=NOS(C)(=O)=O)C#N)C=C1 HLPNGVWWQPWYDF-UHFFFAOYSA-N 0.000 description 3
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
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• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
• YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
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