JP3992725B2 - オキシムエステル化合物及び該化合物を含有する光重合開始剤 - Google Patents
オキシムエステル化合物及び該化合物を含有する光重合開始剤 Download PDFInfo
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- JP3992725B2 JP3992725B2 JP2006531510A JP2006531510A JP3992725B2 JP 3992725 B2 JP3992725 B2 JP 3992725B2 JP 2006531510 A JP2006531510 A JP 2006531510A JP 2006531510 A JP2006531510 A JP 2006531510A JP 3992725 B2 JP3992725 B2 JP 3992725B2
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- Prior art keywords
- alkyl group
- compound
- photosensitive composition
- oxime ester
- meth
- Prior art date
- 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.)
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- -1 Oxime ester compound Chemical class 0.000 title claims description 110
- 150000001875 compounds Chemical class 0.000 title claims description 70
- 239000003999 initiator Substances 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 238000004040 coloring Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 54
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 29
- 239000004593 Epoxy Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229920006243 acrylic copolymer Polymers 0.000 description 18
- 239000000049 pigment Substances 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 11
- 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 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 230000035945 sensitivity Effects 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000003855 acyl compounds Chemical class 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical group C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000009529 body temperature measurement Methods 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 125000006091 1,3-dioxolane group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- 229920002554 vinyl polymer Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-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
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical group CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D409/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Photolithography (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymerisation Methods In General (AREA)
Description
また、R及びR’を置換してもよいハロゲン原子としては、上記のアルキル基の例示からも明らかなようにフッ素が挙げられる他、塩素、臭素、ヨウ素も挙げられる。また、R及びR’を置換してもよい複素環基としては、例えば、ピリジル、ピリミジル、フリル、ベンゾオキサゾール−2−イル、テトラヒドロピラニル、ピロリジル、イミダゾリジル、ピラゾリジル、チアゾリジル、イソチアゾリジル、オキサゾリジル、イソオキサゾリジル、ピペリジル、ピペラジル、モルホリニル等の5〜7員複素環基が挙げられる。
本発明の感光性組成物は、エチレン性不飽和結合を有する重合性化合物に、上述の本発明のオキシムエステル化合物を有効成分とする光重合開始剤を含有させてなるものである。
これらの中でも、スチレン、メチル(メタ)アクリレート、n−ブチル(メタ)アクリレート、ヒドロキシエチル(メタ)アクリレートに、本発明のオキシムエステル化合物を有効成分とする光重合開始剤は好適である。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4−エポキシ−6−メチルシクロヘキシルメチル−3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、1−エポキシエチル−3,4−エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステルなどのグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジルP−アミノフェノール、N,N−ジグリシジルアニリンなどのグリシジルアミン類;1,3−ジグリシジル−5,5−ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物、トリフェニルメタン型エポキシ化合物、ジシクロペンタジエン型エポキシ化合物等も用いることができる。
<ステップ1>4−フルオロ−2−メチル安息香酸クロリドの製造
下記[化30]に示す構造を持つ4−フルオロ−2−メチル安息香酸クロリドを、以下のようにして製造した。
IR測定:(cm-1)
2985、2931、1766、1606、1579、1486、1450、1384、1240、1189、1105、964、869、823
下記[化31]に示すアシル体を、以下のようにして製造した。
1H−NMR測定:(ppm)
8.70(s:1H)、8.52(s:1H)、8.17(d:1H)、8.09(d:1H)、7.50(s:1H)、7.48(d:1H)、7.39(d:1H)、7.05(d:1H)、7.00(d:1H)、4.45(d:2H)、2.73(s:3H)、2.37(s:3H)、1.49(t:3H)
IR測定:(cm-1)
3448、3054、2064、1662、1625、1589、1567、1484、1386、1305、1245、1153、1124、1022、809
窒素気流下、ステップ2で得られたアシル体の541g(1.45モル)、2,2−ジメチル−1,3−ジオキソラン−4−メタノール383g(2.90モル)、テトラブチルアンモニウムハイドロジェンサルフェート98.5g(0.290モル)及びジメチルアセトアミド2.11kgを仕込み、25〜30℃で水酸化ナトリウム145g(3.63モル)を加え、60℃で3時間撹拌した。室温まで冷却し、塩酸ヒドロキシルアミン161g(2.32モル)を加えて80℃で2時間撹拌し、50℃まで冷却した。酢酸ブチル1.45kg及び水1.45kgを加えて油層を分離し、続いて5%食塩水1.45gを加えて油層を洗浄した。油層を分離し、80〜90℃で4時間かけて還流脱水後、酢酸ブチル787g及び無水酢酸178g(1.74モル)を加え、83〜85℃で2時間撹拌した。室温まで冷却し、5%水酸化ナトリウム水溶液1.39kgを加えて油層分離を行ない、続いて水1.57kgを2回に分けて加えて油層を洗浄した。油層をろ過し、溶媒を留去して、酢酸ブチル1.42kg−ブチルエーテル779g混合溶媒から晶析を行った。ろ過、乾燥を経て、無色結晶562g(収率71.4%、HPLC純度99.4%)を得た。該無色結晶について各種分析を行ったところ、該無色結晶は目的物である化合物No.1であることが確認された。分析結果を以下に示す。
(1)融点:123℃
(2)1H−NMR測定:(ppm)
8.5−6.8(arom:9H)、4.6(m:1H)、4.4(q:2H)、4.2(m:1H)、4.1(m:1H)、4.0(m:1H)、2.5(s:3H)、2.4(s:3H)、2.3(s:3H)、1.5(s:3H)、1.4(s:6H)
(3)IR測定:(cm‐1)
2981、2932、1751、1650、1627、1591、1570、1488、1459、1375、1276、1239、1215、1152、1129、1050、894、849、810、773
(4)UVスペクトル測定(アセトニトリル:水=7:3)
λmax=268、292、332nm
(5)分解温度測定(窒素ガス雰囲気下、昇温速度10℃/分、5%重量減少温度)
298℃
窒素気流下、テトラヒドロフルフリルアルコール102.1g(1.0モル)及び1,3−ジメチル−2−イミダゾリジノン(DMI)91.0gを仕込み、30〜40℃でカリウム−t−ブトキシド33.7g(0.30モル)を加えて75℃まで昇温した。続いて実施例1のステップ2で得られたアシル体の74.7g(0.20モル)及びDMI182gを5分かけて加えると80℃まで発熱した。80℃で1時間攪拌後、塩酸ヒドロキシルアミン25.0g(0.36モル)を加えて80℃で40分間攪拌し、室温まで冷却した。酢酸n−プロピル190g及び4%水酸化カリウム水溶液95gを加え、さらに水95gを加えて油層を分離し、水190gを2回に分けて加え、続いて2%水酸化カリウム水溶液95g、さらに水95gを加えて油層を洗浄した。油層を分離し、80〜90℃で2時間かけて還流脱水後、酢酸プロピル102g及び無水酢酸24.5g(0.24モル)を加え、80℃で20分間攪拌した。室温まで冷却し、溶媒を留去して、酢酸プロピル120g−ヘプタン50g混合溶媒から晶析を行った。ろ過、乾燥を経て、無色結晶19.9g(収率19%、HPLC純度99.6%)を得た。該無色結晶について各種分析を行ったところ、該無色結晶は目的物である化合物No.11であることが確認された。分析結果を以下に示す。
(1)融点:119.3℃
(2)1H−NMR測定:(ppm)
8.48(d:1H)、8.43(d:1H)、8.08(dd:1H)、7.99(dd:1H)、7.46(d:1H)、7.44(d:1H)、7.37(d:1H)、6.90(d:1H)、6.82(dd:1H)、4.45−4.40(q:2H)、4.36−4.30(m:1H)、4.06(dd:2H)、4.00−3.95(m:1H)、3.90−3.84(m:1H)、2.52(s:3H)、2.39(s:3H)、2.30(s:3H)、2.18‐1.94(m:3H)、1.86−1.77(m:1H)、1.48(t:3H)
(3)IR測定:(cm‐1)
2972、2872、1752、1644、1626、1590、1487、1453、1375、1309、1276、1239、1176、1145、1129、1082、1036、1009、982、931、895、823、810、773、722
(4)UVスペクトル測定(アセトニトリル:水=9:1)
λmax=273、299、341nm
(5)分解温度測定(窒素ガス雰囲気下、昇温速度10℃/分、5%重量減少温度)
306.5℃
窒素気流下、フルフリルアルコール15.7g(0.16モル)、カリウム−t−ブトキシド4.5g(0.040モル)及びジメチルアセトアミド(DMAc)4.7gを仕込み、75〜80℃まで昇温した。続いて実施例1のステップ2で得られたアシル体の8.0g(0.020モル)及びDMAc18.7gを30分かけて加えた。75〜80℃で1時間攪拌後、30℃に冷却してカリウム−t−ブトキシド1.1g(0.010モル)及び塩酸ヒドロキシルアミン1.9g(0.028モル)を加えて95〜100℃で1時間攪拌し、室温まで冷却した。酢酸n−ブチル10g及び水20gを3回加えて油層を分離し、硫酸マグネシウムで脱水後、無水酢酸2.5g(0.024モル)を加え、80〜85℃で1時間攪拌した。ジブチルエーテル40gを加えて再結晶を行い、ろ過、ジブチルエーテル5gによる洗浄、乾燥を経て、無色結晶7.4g(収率72%、HPLC純度98.9%)を得た。
(1)融点:163.8℃
(2)1H−NMR測定:(ppm)
8.50(d:1H)、8.44(d:1H)、8.08(dd:1H)、7.99(dd:1H)、7.48(dd:1H)、7.46(d:1H)、7.44(d:1H)、7.38(d:1H)、6.96(d:1H)、6.89(dd:1H)、6.49(d:1H)、6.42(dd:1H)、5.09(s:1H)、4.42(q:2H)、2.51(s:3H)、2.40(s:3H)、2.29(s:3H)、1.48(t:3H)
(3)IR測定:(cm‐1)
2979、2933、1769、1650、1627、1595、1570、1488、1451、1374、1317、1273、1238、1206、1177、1150、1129、1102、1078、1019、995、933、883、812、790、772、758、716、703
(4)UVスペクトル測定(アセトニトリル:水=9:1)
λmax=273、297、341nm
(5)分解温度測定(窒素ガス雰囲気下、昇温速度10℃/分、5%重量減少温度)
318.5℃
アクリル系共重合体14gに対し、トリメチロールプロパントリアクリレート5.9g、実施例1で得られた化合物No.1の2.7g及びエチルセロソルブ79gを加えて良く撹拌し、感光性組成物No.1を得た。
尚、上記アクリル系共重合体は、メタクリル酸20質量部、ヒドロキシエチルメタクリレート15質量部、メチルメタクリレート10質量部及びブチルメタクリレート55質量部をエチルセロソルブ300質量部に溶解し、窒素雰囲気下でアゾビスイソブチルニトリル0.75質量部を加えて70℃で5時間反応させることにより得られたものである。
実施例4で用いたものと同じアクリル系共重合体7.2gに、トリメチロールプロパントリアクリレート4.3g、実施例1で得られた化合物No.1の2.0g及びエチルセロソルブ87gを加えて良く撹拌し、感光性組成物No.2を得た。
スチレン−アクリル系感光性共重合体14gに、ジペンタエリスリトールヘキサアクリレート6.0g、実施例1で得られた化合物No.1の1.3g、2,2−ビス(2−クロロフェニル)− 4,5,4',5'−テトラフェニル− 1−2'−ビイミダゾール1.3g及びエチルセロソルブ83gを加えて良く撹拌し、感光性組成物No.3を得た。
尚、上記スチレン−アクリル系感光性共重合体は、スチレン26.3質量部、2−ヒドロキシメタクリレート43.8質量部、メタクリル酸35質量部及びメタクリル酸エチル70質量部をエチルセロソルブ175質量部に溶解し、窒素雰囲気下でアゾビスイソブチルニトリル0.75質量部を加え90℃で5時間反応させ、次いで、イソシアネートエチルメタクリレート23.5質量部、オクチル酸錫0.11質量部をエチルセロソルブ20質量部で溶解したものを約10分かけて滴下し、滴下後2時間反応させることにより得られたものである。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体12gに、ジペンタエリスリトールペンタ及びヘキサアクリレート8.1g、実施例1で得られた化合物No.1の2.5g、エチルセロソルブ47g及びシクロヘキサノン30gを加えて良く撹拌し、感光性組成物No.4を得た。
実施例4で用いたものと同じアクリル系共重合体20gに、トリメチロールプロパントリアクリレート8.7g、実施例1で得られた化合物No.1の2.2g、ビスフェノールA型エポキシ樹脂4.6g及びエチルセロソルブ65gを加えて良く撹拌し、感光性組成物No.5を得た。
実施例4で用いたものと同じアクリル系共重合体14gに対し、トリメチロールプロパントリアクリレート5.9g、実施例2で得られた化合物No.11の2.7g及びエチルセロソルブ79gを加えて良く攪拌し、感光性組成物No.6を得た。
実施例4で用いたものと同じアクリル系共重合体7.2gに、トリメチロールプロパントリアクリレート4.3g、実施例2で得られた化合物No.11の2.0g及びエチルセロソルブ87gを加えて良く攪拌し、感光性組成物No.7を得た。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体14gに対し、ジペンタエリスリトールヘキサアクリレート6.0g、実施例2で得られた化合物No.11の1.3g、2,2−ビス(2−クロロフェニル)−4,5,4',5'−テトラフェニル− 1−2'−ビイミダゾール1.3g及びエチルセロソルブ83gを加えて良く攪拌し、感光性組成物No.8を得た。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体12gに対し、ジペンタエリスリトールペンタ及びヘキサアクリレート8.1g、実施例2で得られた化合物No.11の2.5g、エチルセロソルブ47g及びシクロヘキサノン30gを加えて良く攪拌し、感光性組成物No.9を得た。
実施例4で用いたものと同じアクリル系共重合体20gに対し、トリメチロールプロパントリアクリレート8.7g、実施例2で得られた化合物No.11の2.2g、ビスフェノールA型エポキシ樹脂4.6g及びエチルセロソルブ65gを加えて良く攪拌し、感光性組成物No.10を得た。
実施例4で用いたものと同じアクリル系共重合体14gに対し、トリメチロールプロパントリアクリレート5.9g、実施例3で得られた化合物No.12の2.7g及びエチルセロソルブ79gを加えて良く攪拌し、感光性組成物No.11を得た。
実施例4で用いたものと同じアクリル系共重合体14gに、ジペンタエリスリトールペンタ及びヘキサアクリレート5.9g、下記[化32]に示す比較化合物1〔分解温度測定(窒素ガス雰囲気下、昇温速度10℃/分、5%重量減少温度):242.1℃〕2.1g及びエチルセロソルブ78gを加えてよく撹拌し、感光性組成物No.12を得た。
アクリル系共重合体の代わりに実施例6で用いたものと同じスチレン−アクリル系感光性共重合体を用いた以外は、比較例1と同一の条件で感光性組成物No.13を得た。
実施例4で用いたものと同じアクリル系共重合体7.2gに、トリメチロールプロパントリアクリレート4.3g、下記[化33]に示す比較化合物2〔分解温度測定(窒素ガス雰囲気下、昇温速度10℃/分、5%重量減少温度):232.2℃〕1.5g及びエチルセロソルブ87gを加えて良く撹拌し、感光性組成物No.14を得た。
アクリル系共重合体の代わりに実施例6で用いたものと同じスチレン−アクリル系感光性共重合体を用いた以外は、比較例3と同一の条件で感光性組成物No.15を得た。
実施例4で用いたものと同じアクリル系共重合体12gに、トリメチロールプロパントリアクリレート8g、実施例1で得られた化合物No.1の2.7g、ピグメントブルー15の1.0g及びエチルセロソルブ79gを加えて良く撹拌し、着色感光性組成物No.1を得た。
実施例4で用いたものと同じアクリル系共重合体6.9gに、トリメチロールプロパントリアクリレート4.3g、実施例1で得られた化合物No.1の2.0g、ピグメントレッド254の1.0g及びエチルセロソルブ87gを加えて良く撹拌し、着色感光性組成物No.2を得た。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体12gに、ジペンタエリスリトールヘキサアクリレート 4.0g、実施例1で得られた化合物No.1の1.3g、2,2−ビス(2−クロロフェニル)−4,5,4',5'−テトラフェニル−1−2'−ビイミダゾール 1.3g、ピグメントレッド254の0.7g、ピグメントイエロー138の0.3g及びエチルセロソルブ83gを加えて良く撹拌し、着色感光性組成物No.3を得た。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体12gに、ジペンタエリスリトールペンタ及びヘキサアクリレート6.1g、実施例1で得られた化合物No.1の2.5g、カーボンブラック3.2g、エチルセロソルブ47g及びシクロヘキサノン 30gを加えて良く撹拌し、着色感光性組成物No.4を得た。
実施例4で用いたものと同じアクリル系共重合体12gに、トリメチロールプロパントリアクリレート8g、実施例2で得られた化合物No.11の2.7g、ピグメントブルー15の1.0g及びエチルセロソルブ79gを加えて良く撹拌し、着色感光性組成物No.5を得た。
実施例4で用いたものと同じアクリル系共重合体6.9gに、トリメチロールプロパントリアクリレート4.3g、実施例2で得られた化合物No.11の2.0g、ピグメントレッド254の1.0g及びエチルセロソルブ87gを加えて良く撹拌し、着色感光性組成物No.6を得た。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体12gに、ジペンタエリスリトールヘキサアクリレート4.0g、実施例2で得られた化合物No.11の1.3g、2,2−ビス(2−クロロフェニル)−4,5,4',5'−テトラフェニル−1−2'−ビイミダゾール1.3g、ピグメントレッド254の0.7g、ピグメントイエロー138の0.3g及びエチルセロソルブ83gを加えて良く撹拌し、着色感光性組成物No.7を得た。
実施例6で用いたものと同じスチレン−アクリル系感光性共重合体12gに、ジペンタエリスリトールペンタ及びヘキサアクリレート6.1g、実施例2で得られた化合物No.11の2.5g、カーボンブラック3.2g、エチルセロソルブ47g及びシクロヘキサノン30gを加えて良く撹拌し、着色感光性組成物No.8を得た。
実施例4で用いたものと同じアクリル系共重合体12gに、ジペンタエリスリトールペンタ及びヘキサアクリレート5.9g、比較化合物1の2.1g、ピグメントブルー15の1.0g及びエチルセロソルブ78gを加えてよく撹拌し、着色感光性組成物No.9を得た。
アクリル系共重合体の代わりに実施例6で用いたものと同じスチレン−アクリル系感光性共重合体を、ピグメントブルー15の1.0gの代わりにカーボンブラック3.2gを用いた以外は、比較例5と同一の条件で着色感光性組成物No.10を得た。
すなわち、基板上にγ−グリシドキシプロピルメチルエトキシシランをスピンコートして良くスピン乾燥させた後、感光性組成物No.1〜15及び着色感光性組成物No.1〜10のいずれかをスピンコート(1300r.p.m、50秒間)し乾燥させた。70℃で20分間プリベークを行った後、ポリビニルアルコール5質量%溶液をコートして酸素遮断膜とした。70℃で20分間の乾燥後、所定のマスクを用い、光源として超高圧水銀ランプを用いて露光後、2.5質量%炭酸ナトリウム溶液に25℃で30秒間浸漬して現像し、良く水洗した。水洗乾燥後、230℃で1時間ベークしてパターンを定着させた。得られたパターンについて、以下の評価を行った。結果を表1及び表2に示す。
露光時に、露光量が100mJ/cm2で十分だったものをa、100mJ/cm2では不十分で、200mJ/cm2で露光したものをbとした。
<解像度>
露光現像時に、線幅10μm未満でも良好にパターン形成できたものをA、線幅10〜30μmであれば良好にパターン形成できたものをB、線幅30μm超でないと良好なパターン形成ができなかったものをCと評価した。
<密着性>
JIS D 0202の試験方法に従い、露光現像した後200℃で30分間加熱した塗膜に基盤目状にクロスカットを入れ、次いでセロハンテープによってピーリングテストを行い、基盤目の剥離の状態を目視により評価した。全く剥離が認められなかったものを○、剥離が認められたものを×とした。
<耐アルカリ性>
露光現像した後、200℃で30分間加熱処理を行った。加熱処理後の塗膜をa)5質量%NaOH水溶液中で24時間、b)4質量%KOH水溶液中で50℃で10分間、c)1質量%NaOH水溶液中で80℃で5分間の条件で浸漬し、浸漬後の外観を目視により評価した。いずれの条件においても外観変化もなくレジストの剥離も全くなかったものを○、いずれかの条件においてレジストの浮きが見られたりレジストの剥離が認められたものを×とした。
それに対して、比較例1〜4の感光性組成物No.12〜No.15及び比較例5〜6の着色感光性組成物No.9〜No.10は、感度が低いため露光量を多くせざるを得ず、解像度が低下し、また、得られた塗膜の基板との耐アルカリ性も思わしくなかった。
さらに、本発明のオキシムエステル化合物は、分解温度が300℃付近であり、公知のオキシムエステル化合物より40〜100℃高く、耐熱性に優れ、熱効果処理温度においても十分安定であり、得られる重合物を着色したり、重合物及び装置を汚染することもなかった。
Claims (9)
- 下記一般式(II)で表されるオキシムエステル化合物。
- 下記一般式(III)で表されるオキシムエステル化合物。
- 下記一般式(IV)で表されるオキシムエステル化合物。
- 上記一般式(II)中のR1がアルキル基であり、R2がアルキル基であり、R3がアルキル基であり、R4がアルキル基であり、R5がアルキル基であり、R6が水素原子であり、R7が水素原子であり、Xがアルキル基であり、Y1が酸素原子であり、Y2が酸素原子であり、Y3が酸素原子であり、pが1又は2であり、qが1である請求の範囲第1項記載のオキシムエステル化合物。
- 上記一般式(III)中のR1がアルキル基であり、R2がアルキル基であり、R3がアルキル基であり、Xがアルキル基であり、Y1が酸素原子であり、pが1又は2であり、qが1である請求の範囲第2項記載のオキシムエステル化合物。
- 上記一般式(IV)中のR1がアルキル基であり、R2がアルキル基であり、R3がアルキル基であり、Xがアルキル基であり、Y1が酸素原子であり、pが1又は2であり、qが1である請求の範囲第3項記載のオキシムエステル化合物。
- 請求の範囲第1〜6項のいずれかに記載のオキシムエステル化合物を有効成分とする光重合開始剤。
- エチレン性不飽和結合を有する重合性化合物に、請求の範囲第7項記載の光重合開始剤を含有させてなる感光性組成物。
- 請求の範囲第8項の感光性組成物に、さらに色材を含んでなる着色感光性組成物。
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