JP7394759B2 - オキシムエステル化合物およびこれを含有する光重合開始剤 - Google Patents
オキシムエステル化合物およびこれを含有する光重合開始剤 Download PDFInfo
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- JP7394759B2 JP7394759B2 JP2020527670A JP2020527670A JP7394759B2 JP 7394759 B2 JP7394759 B2 JP 7394759B2 JP 2020527670 A JP2020527670 A JP 2020527670A JP 2020527670 A JP2020527670 A JP 2020527670A JP 7394759 B2 JP7394759 B2 JP 7394759B2
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- -1 Oxime ester compound Chemical class 0.000 title claims description 149
- 239000003999 initiator Substances 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 218
- 125000004432 carbon atom Chemical group C* 0.000 claims description 173
- 239000000203 mixture Substances 0.000 claims description 82
- 238000004519 manufacturing process Methods 0.000 claims description 80
- 125000000623 heterocyclic group Chemical group 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 239000003505 polymerization initiator Substances 0.000 claims description 42
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000003700 epoxy group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 239000003086 colorant Substances 0.000 claims description 15
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052711 selenium Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 9
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- 125000001931 aliphatic group Chemical group 0.000 description 15
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- 125000001424 substituent group Chemical group 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 12
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
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- 239000011737 fluorine Substances 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 150000002484 inorganic compounds Chemical class 0.000 description 6
- 229910010272 inorganic material Inorganic materials 0.000 description 6
- 125000003566 oxetanyl group Chemical group 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
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- 150000002148 esters Chemical class 0.000 description 5
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 229940049920 malate Drugs 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 5
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- 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 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- JUADTOTVJUYCRQ-UHFFFAOYSA-N 3-cyclohexylpropanoyl chloride Chemical compound ClC(=O)CCC1CCCCC1 JUADTOTVJUYCRQ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- APNSGVMLAYLYCT-UHFFFAOYSA-N isobutyl nitrite Chemical compound CC(C)CON=O APNSGVMLAYLYCT-UHFFFAOYSA-N 0.000 description 3
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- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
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- 125000006850 spacer group Chemical group 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
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- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003273 ketjen black Substances 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
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- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- YLNSNVGRSIOCEU-UHFFFAOYSA-N oxiran-2-ylmethyl butanoate Chemical compound CCCC(=O)OCC1CO1 YLNSNVGRSIOCEU-UHFFFAOYSA-N 0.000 description 1
- CSVRUJBOWHSVMA-UHFFFAOYSA-N oxolan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCO1 CSVRUJBOWHSVMA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl 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])C([H])([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 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
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- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Classifications
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
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- 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
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- 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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- G—PHYSICS
- G02—OPTICS
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- G—PHYSICS
- G02—OPTICS
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- G02B5/00—Optical elements other than lenses
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- 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
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- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
Description
で表される基と、オキシムエステル基を有さない光ラジカル開裂性基と、を同一分子内に有することを特徴とするものである。ここで、一般式(I)中、R1およびR2は、それぞれ独立に水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基または炭素原子数2~20の複素環含有基を表し、
R1およびR2で表される基中の水素原子の1つまたは2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基または炭素原子数2~20の複素環含有基で置換されていてもよく、
R1およびR2で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-NR3-、-NR3CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-またはCSO-で置換されていてもよく、
R3は、水素原子、炭素原子数1~20の炭化水素基を表し、
nは0または1を表し、*は結合手を表す。
R11は、前記一般式(I)で表される基を表し、
R12は、前記オキシムエステル基を有さない光ラジカル開裂性基、前記オキシムエステル基を有さない光ラジカル開裂性基で置換された炭素原子数1~20の炭化水素基、または前記オキシムエステル基を有さない光ラジカル開裂性基で置換された炭素原子数2~20の複素環含有基を表し、
R13は、それぞれ独立にハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基または炭素原子数2~20の複素環含有基を表し、
R12およびR13で表される基中の水素原子の1つまたは2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基または炭素原子数2~20の複素環含有基で置換されていてもよく、
R12およびR13で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-NR14-、-NR14CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-またはCSO-で置換されていてもよく、
R14は、水素原子、炭素原子数1~20の炭化水素基を表し、
aは1~20の整数を表し、aが2以上の整数の場合、複数存在するR11は、同一であっても異なっていてもよく、
bは1~20の整数を表し、bが2以上の整数の場合、複数存在するR12は、同一であっても異なっていてもよく、
cは0~20の整数を表し、cが2以上の整数の場合、複数存在するR13は、同一であっても異なっていてもよいが、
a+b+cは20以下である。
X2は、単結合、無結合、酸素原子、硫黄原子、セレン原子、CR21R22、CO、NR23またはPR24を表し、
R21、R22、R23およびR24は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基または複素環を含有する炭素原子数2~20の基を表し、R21、R22、R23およびR24で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアン基、水酸基、カルボキシル基または炭素原子数2~20の複素環基で置換されていてもよく、
R21、R22、R23およびR24で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-に置換されていてもよい。
R32およびR33は、R41またはOR41を表し、
R32とR33は結合して環を形成していてもよく、
R41は、水素原子または炭素原子数1~20の炭化水素基を表し、
R42およびR43は、炭素原子数1~20の炭化水素基を表し、
R71は、炭素原子数1~20の炭化水素基を表し、
R72およびR73は、R41またはOR41を表し、
R34、R35、R36、R37、R38、R39、R40、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6およびAr7は、炭素原子数6~20のアリール基を表し、
v1、v2、v3、v4、v5、v6およびv7は、0または1を表し、*は、結合手を表す。
で表される基と、オキシムエステル基を有さない光ラジカル開裂性基と、を同一分子内に有する化合物である。本発明のオキシムエステル化合物には、オキシムの二重結合による幾何異性体が存在するが、これらを区別するものではない。すなわち、本明細書において、本発明のオキシムエステル化合物およびその例示化合物は、これら幾何異性体の一種または二種以上の混合物を表すものであり、特定の異性体を示した構造に限定するものではない。なお、オキシムエステル基を有さない光ラジカル開裂性基とは、紫外線などの光(活性エネルギー)を照射されることで、開裂しラジカルを発生するオキシムエステル基以外の基を意味する。
R1およびR2で表される基中の水素原子の1つまたは2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基または炭素原子数2~20の複素環含有基で置換されていてもよく、
R1およびR2で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-NR3-、-NR3CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-またはCSO-で置換されていてもよく、
R3は、水素原子、炭素原子数1~20の炭化水素基を表し、
nは0または1を表し、*は結合手を表す。
R11は、一般式(I)で表される基を表し、
R12は、オキシムエステル基を有さない光ラジカル開裂性基、オキシムエステル基を有さない光ラジカル開裂性基で置換された炭素原子数1~20の炭化水素基、またはオキシムエステル基を有さない光ラジカル開裂性基で置換された炭素原子数2~20の複素環含有基を表し、
R13は、それぞれ独立にハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基または炭素原子数2~20の複素環含有基を表し、
R12およびR13で表される基中の水素原子の1つまたは2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基または炭素原子数2~20の複素環含有基で置換されていてもよく、
R12およびR13で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-NR14-、-NR14CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-またはCSO-で置換されていてもよく、
R14は、水素原子、炭素原子数1~20の炭化水素基を表し、
aは1~20の整数を表し、aが2以上の整数の場合、複数存在するR11は、同一であっても異なっていてもよく、
bは1~20の整数を表し、bが2以上の整数の場合、複数存在するR12は、同一であっても異なっていてもよく、
cは0~20の整数を表し、cが2以上の整数の場合、複数存在するR13は、同一であっても異なっていてもよいが、a+b+cは20以下である。
R32とR33は結合して環を形成していてもよく、R41は、水素原子または炭素原子数1~20の炭化水素基を表し、R42およびR43は、炭素原子数1~20の炭化水素基を表し、R71は、炭素原子数1~20の炭化水素基を表し、R72およびR73は、R41またはOR41を表し、R34、R35、R36、R37、R38、R39、R40、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6およびAr7は、炭素原子数6~20のアリール基を表し、v1、v2、v3、v4、v5、v6およびv7は、0または1を表し、*は、結合手を表す。
R51およびR52は、それぞれ独立に、水素原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基または複素環を含有する炭素原子数2~20の基を表し、炭素原子数1~20の炭化水素基としては、炭素原子数1~20のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基が好ましく、
X11は、酸素原子、硫黄原子、セレン原子、CR53R54、CO、NR55またはPR56を表し、
X12は、無結合、直接結合、炭素原子数1~20の炭化水素基、COを表し、
R53~R56は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基または複素環を含有する炭素原子数2~20の基を表し、R53~R56で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、メルカプト基、イソシアネート基、複素環含有基で置換される場合もあり、
R51~R56で表される基中のメチレン基は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-S-、-SO2-、-SCO-または-COS-で置換される場合もあり、
R51~R56は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成する場合もあり、
dは0~4の数を、eは0~3の数を表す。
で表される構造単位であることが望ましい。
(メタ)アクリル酸シクロアルキルエステルとして、例えば、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸2-メチルシクロヘキシル、(メタ)アクリル酸トリシクロ[5.2.1.02,6]デカン-8-イル、(メタ)アクリル酸2-(トリシクロ[5.2.1.02,6]デカン-8-イルオキシ)エチル、(メタ)アクリル酸イソボロニル等を挙げることができる。
(メタ)アクリル酸アラルキルエステルとして、例えば、(メタ)アクリル酸ベンジル等を挙げることができる。
化合物(u2):好ましくは1モル%~95モル%、より好ましくは10モル%~60モル%、さらに好ましくは20モル%~30モル%
化合物(u3):好ましくは50モル%以下、より好ましくは1モル%~40モル%、さらに好ましくは10モル%~30モル%
化合物(u4):好ましくは80モル%以下、より好ましくは1モル%~60モル%、さらに好ましくは25モル%~50モル%
の範囲で使用することが好ましい。
R61、およびR62がそれぞれ複数存在する場合は、同一の場合も異なる場合もあり、fは、0~4の整数であり、gは、0~4の整数であり、mは0~10の整数であり、
mが0で無い場合に存在する光学異性体は、どの異性体でもよい。
R81、R82、R83、R84およびR85のうち少なくとも1つは水素原子でなく、
R86は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基またはトリアルキルシリル基を表す。
X7は、下記一般式(2)で表される基であり、
R92、R93、R94およびR95は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基または炭素原子数2~20の複素環含有基を表し、
R92、R93、R94およびR95のうち少なくとも1つは水素原子でない。
脂肪族炭化水素基中のメチレン基は、-O-、-S-、-CO-、-COO-、-OCO-または-NH-、あるいは酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置換されていてもよく、
R97およびR98は、水素原子、炭素原子数1~8のアルキル基、炭素原子数6~20のアリール基または炭素原子数7~20のアリールアルキル基を表し、
Z5およびZ6は、それぞれ独立に、直接結合、-O-、-S-、>CO、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-または>NR100を表し、
R99およびR100は、水素原子、置換基を有していてもよい炭素原子数1~35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香族炭化水素基または置換基を有していてもよい炭素原子数2~35の複素環基を表し、*は結合手を表す。
Chemie製);メガファックF-114、メガファックF-410、メガファックF-444、メガファックEXP TP-2066、メガファックF-430、メガファックF-472SF、メガファックF-477、メガファックF-552、メガファックF-553、メガファックF-554、メガファックF-555、メガファックR-94、メガファックRS-72-K、メガファックRS-75、メガファックF-556、メガファックEXP TF-1367、メガファックEXP TF-1437、メガファックF-558、メガファックEXP TF-1537(以上、DIC製);FC-4430、FC-4432(以上、住友スリーエム製);フタージェント 100、フタージェント 100C、フタージェント 110、フタージェント 150、フタージェント 150CH、フタージェント A-K、フタージェント 501、フタージェント 250、フタージェント 251、フタージェント 222F、フタージェント 208G、フタージェント 300、フタージェント 310、フタージェント 400SW(以上、ネオス製);PF-136A、PF-156A、PF-151N、PF-636、PF-6320、PF-656、PF-6520」、PF-651、PF-652、PF-3320(以上、北村化学産業製)等の市販品を使用することができる。
四つ口フラスコに塩化アルミニウム(16.8g、126mmol)、ジクロロエタン120.0gを仕込み、氷冷下、エチルカルバゾール(23.4g、120mmol)、3-シクロヘキシルプロパノイルクロリド(16.8g、126mmol)の順に仕込んだ。室温で1時間反応させたのち、反応液を氷水にあけ、油水分離を行った。有機層をイオン交換水で3回洗浄行った後、脱溶媒後、淡黄色固体の中間体1-Aを得た(32.4g、収率81%)。
四つ口フラスコに塩化アルミニウム(17.4g、131mmol)、ジクロロエタン90.0gを仕込み、氷冷下、中間体1-A(20.7g、62.2mmol)、2-ブロモイソブチリルブロミド(15.0g、65.3mmol)の順に仕込んだ。室温で1時間反応させたのち、反応液を氷水にあけ、油水分離を行った。有機層をイオン交換水で3回洗浄行った後、脱溶媒後、淡黄色固体の中間体1-Bを得た(27.0g、収率90%)。
中間体1-B(30.0g、62.2mmol)、キシレン(54.2g)、メタノール(27.1g)、炭酸カリウム(17.2g、124.4mmol)gを仕込み、室温で3時間撹拌した。無機塩をろ別し、ろ液を脱溶媒後、淡黄色油状の中間体1-Cを得た(27.1g、収率100%)。
四つ口フラスコに中間体1-C(27.1g、62.2mmol)、モルホリン81.3gを仕込み、窒素気流下還流を行った。12時間撹拌反応後、脱溶媒を行った。酢酸エチル、1%塩酸を仕込み撹拌後、油水分離を行った。有機層を3回水洗し、脱溶媒後、淡黄色油状の中間体1-Dを得た(28.9g、収率95%)。
四つ口フラスコに中間体1-D(8.73g、17.8mmol)、DMF30.0g、5℃で撹拌しながら35%塩酸4.0g、亜硝酸イソブチル(3.87g、37.5mmol)を仕込み、室温で12時間反応させた。酢酸エチルを仕込み、油水分離後、有機層を3回水洗し、脱溶媒後、中間体1-Eを得た(9.0g、収率97%)。
四つ口フラスコに中間体1-E(9.24g、17.9mmol)、酢酸エチル30.0gを仕込み、氷冷下、塩化アセチル(1.54g、19.7mmol)、トリエチルアミン(1.99g、19.7mmol)の順に滴下した。室温で1時間撹拌後、イオン交換水を仕込み油水分離を行った。有機層を3回水洗し、脱溶媒後、シリカゲルカラム(酢酸エチル/ヘキサン=3/10)に付し、化合物No.1-1を得た(2.1g、収率21%)。得られた化合物No.1-1のNMRデータを[表1]に示す。
中間体1-Aの製造に用いた3-シクロヘキシルプロパノイルクロリドを、ベンゾイルフォルミルクロライドに、中間体1-Bの製造に用いた酸クロライドを、オクタノイルクロライドに変更した以外、製造例1と同様の方法で、中間体1-7-Aを得た。
中間体1-7-A(9.1g、20.0mmol)、ジオキサン(30.0g)、ジメチル硫酸(3.2g、60.0mmol)を仕込み、室温を保持しながらナトリウムメチラート(3.2g、60.0mmol)を添加した。室温で5時間反応させた後、酢酸エチル、イオン交換水を仕込み、油水分離した。有機層を3回水洗後、脱溶媒し、シリカゲルカラムに付し、中間体1-7-Bを得た。
中間体1-Dを中間体1-7-Bに変更した以外、製造例1と同様の方法で、化合物No.1-7を得た。
中間体1-Dを製造する際に用いたモルホリンを、ピペリジンに変更した以外、製造例1と同様の方法で化合物No.1-71を得た。得られた化合物No.1-71のNMRデータを[表1]に示す。
(1)中間体1-72-Aの製造
化合物1-B(5.75g、11.9mmol)、THF(17.2g)、イオン交換水(17.2g)、48%水酸化ナトリウム水溶液(1.1g)を仕込み、室温で24時間反応させた。酢酸エチルで抽出を行い、有機層を3回水洗後、脱溶媒し、中間体1-72-Aを得た。
その後、製造例1と同様にして、化合物No.1-72を得た。得られた化合物No.1-72のNMRデータを[表1]に示す。
中間体1-Bの製造の際に用いた、酸クロライドをシクロヘキサンカルボニルクロライドに変更した以外、実施例1と同様の方法で中間体1-73-Aを得た。
中間体1-73-A(11.9g、39.0mmol)、塩化メチレン(50g)を仕込み、氷冷下、臭素(6.8g、42.9mmol)をゆっくり仕込んだ。室温で1時間反応させた後、脱溶媒し、中間体1-73-Bを得た。
中間体1-73-B(5.9g、15.6mmol)、THF(12.0g)、イオン交換水(12.0g)、48%水酸化ナトリウム水溶液(1.9g)を仕込み、室温で24時間反応させた。酢酸エチルで抽出を行い、有機層を3回水洗後、脱溶媒し、中間体1-73-Cを得た。
中間体1-Aの製造の際に用いたエチルカルバゾールを、中間体1-73-Cに変更し、3-シクロヘキシルプロパノイルクロリドをオクタノイルクロライドに変更した以外、中間体1-Aの製造と同様の方法で中間体1-73-Dを得た。
中間体1-Dを中間体1-73-Dに変更した以外、製造例1と同様の方法で、化合物No.1-73を得た。
中間体1-7-Bの製造と同様の方法で得られた異性体として中間体1-74-Aを得た。なお、化合物No.1-7の中間体1-7-Bと、化合物No.1-74の中間体1-74-Aは、同一の製造方法で製造される異性体であり、シリカゲルカラムを用いて精製分離した。
その後、中間体1-Dを中間体1-74-Aに変更した以外、製造例1と同様の方法で、化合物No.1-74を得た。
中間体-75-A(10.0g,20.7mmol)、アセトン(30.0g)、ジメチルアミン50%水溶液(5.6g,62.2mol)、炭酸カリウム(4.3g,31.1mmol)を仕込み、室温で4時間撹拌した。反応後、酢酸エチル、イオン交換水を仕込み、油水分離した。有機層を3回水洗し、脱溶媒後、中間体1-75-Bを得た。
中間体1-75-B(8.3g,18.6mmol)、酢酸エチル(30.0g)、イオン交換水(30.0g)、ベンジルブロミド(3.5g,20.5mmol)、48%水酸化ナトリウム(1.7g,20.5mmol)を仕込み、室温で3時間反応させた。反応後、酢酸エチル、イオン交換水を仕込み、油水分離した。有機層を3回水洗し、脱溶媒後、シリカゲルカラムに付し、中間体1-75-Cを得た。
中間体1-Dを中間体1-75-Cに変更した以外、製造例1と同様の方法で、化合物No.1-75を得た。
中間体1-Dを中間体1-76-Aに変更した以外、製造例1と同様の方法で、化合物No.1-76を得た。得られた化合物No.1-76のNMRデータを[表1]に示す。
四つ口フラスコに中間体2-A(12.7g、47.4mmol)、中間体2-B(10.5g、43.1mol)、炭酸カリウム(11.9g、86.3mmol)、ジメチルフォルムアセトアミド60.0gを仕込み、窒素気流下加熱還流を12時間行った。室温まで冷却後、イオン交換水、酢酸エチルを仕込み、60℃で油水分離を行った。有機層を60℃に加温しながら3回水洗し、室温まで冷却後、析出物をろ別し、中間体2-Cを得た(8.5g、収率57%)。
四つ口ナスフラスコに中間体2-C(4.35g、9.16mmol)、DMF(40.0g)を仕込み、氷冷下撹拌しながら35%塩酸(2.00g)、亜硝酸イソブチル(1.98、10.1mol)を滴下し、40℃で30時間撹拌した。イオン交換水、酢酸エチルを加え、油水分離し、有機層を3回水洗した。次に有機層へ氷冷下、塩化アセチル(1.51g、19.2mmol)、トリエチルアミン(1.95g、19.2mmol)を滴下した。室温で1時間撹拌後、イオン交換水を加え、油水分離し有機層を3回水洗した。脱溶媒後、シリカゲルカラム(酢酸エチル/ヘキサン=2/10)に付し、化合物No.2-1(2.1g:収率45%)を得た。得られた化合物No.2-1のNMRデータを[表1]に示す。
塩化アルミニウム(309.56g、71.7mmol)、ジクロロエタン(30.0g)を仕込み、氷冷下、フルオレン(3.97g、23.9mmol)、オクタノイルクロライド(7.97g、49.0mmol)の順に仕込んだ。室温で1時間反応させたのち、反応液を氷水中に注ぎ、析出物をろ別した。イオン交換水、メタノールで洗浄し、中間体4-72-Aを得た。
得られた中間体4-72-Aに対し、中間体2-Cの合成と同様にして中間体4-72-Bを得た。
化合物No.2-1の製造と同様にして、化合物No.4-72を得た。得られた化合物No.4-72のNMRデータを[表1]に示す。
分散剤としてDISPERBYK-161(12.5質量部;ビックケミージャパン製)および着色剤としてピグメントブルー15:6(15質量部)を、PGMEA(72.5質量部)に、ビーズミルを使用して分散させてブルー顔料分散液を製造した。
[表2]、[表3]の配合に従って各成分を調製し、実施例1~15および比較例1~4の重合性組成物を得た。なお、表中の数字は質量部を表す。
A-1 :化合物No.1-1
A-2 :化合物No.1-7
A-3 :化合物No.1-14
A-4 :化合物No.1-70
A-5 :化合物No.1-71
A-6 :化合物No.1-72
A-7 :化合物No.1-73
A-8 :化合物No.1-74
A-9 :化合物No.1-75
A-10:化合物No.1-76
A-11:化合物No.2-1
A-12:化合物No.3-1
A-13:化合物No.4-71
A-14:化合物No.4-72
A-15:化合物No.6-1
A’-1:化合物No.A2-9
A’-2:2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパン-1-オン
B-1 :SPC-3000(カルボキシル基を有する重合体;昭和電工社製、固形分42.7%、PGMEA溶液)
C-1 :カヤラッドDPHA(エチレン性不飽和化合物;日本化薬社製)
D-1 :ブルー顔料分散液No.1
E-1 :KBE-403(カップリング剤、信越化学株式会社製)
F-1 :PGMEA(溶剤)
得られた重合性組成物およびその硬化物において感度および輝度の評価を下記の手順で行った。結果を[表2]、[表3]に併記する。
ガラス基板上に各重合性組成物をスピンコート(ポストベイク後の色度座標(x、y)=(0.135,0.098)になるように)し、ホットプレートを用いて、90℃で120秒間プリベイクを行った後、23℃で60秒間冷却した。その後、超高圧水銀ランプを用いてフォトマスク(マスク開口30μm)を介して露光した(露光ギャップ100μm、露光量40mJ/cm2)。現像液として0.04質量%KOH水溶液を用いて現像した後、よく水洗し、クリーンオーブンを用いて230℃で20分ポストベイクを行い、パターンを定着させた。得られたパターンを電子顕微鏡で観察し、マスク開口に対応する部分の線幅を測定した。
ガラス基板上に各重合性組成物をスピンコート(ポストベイク後の色度座標(x、y)=(0.135,0.098)になるように)し、ホットプレートを用いて、90℃で120秒間プリベイクを行った後、23℃で60秒間冷却した。その後、超高圧水銀ランプを用いて150mJ/cm2で露光後、クリーンオーブンを用いて230℃で20分ポストベイクを行い、評価サンプルを作成した。得られたサンプルの380~780nmにおける透過率から、JIS Z8701に準拠してY値を求めた。Y値が高いほど輝度が高く可視光領域において高い透過率を有することを意味し、有用である。Y値が9.5以上のものは、カラーフィルタとして使用でき、Y値が11.0以上の物は特に好ましく使用でき、Y値が9.5未満のものはカラーフィルタとして適さない。
[表4]に記載の化合物を試料として採取し、示差熱熱重量同時測定装置(エスアイアイ・ナノテクノロジー社製、型式:EXSTAR TG/DTA6200」)を用いて、試料約5~10mg、窒素200mL/min雰囲気下、昇温開始温度30℃、昇温終了温度500℃、昇温速度10℃/minで昇温した際における試料について熱減量を測定した。30℃時点の試料重量に対して10%減量した時点の温度を10%重量減少温度とした。なお、10%重量減少温度が230℃以上で、耐熱性に優れる光ラジカル重合開始剤として用いることができる。
Claims (11)
- 下記一般式(I)で表される基と、オキシムエステル基を有さない光ラジカル開裂性基と、を同一分子内に有することを特徴とするオキシムエステル化合物。
(一般式(I)中、R1およびR2は、それぞれ独立に水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基または炭素原子数2~20の複素環含有基を表し、
R1およびR2で表される基中の水素原子の1つまたは2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基または炭素原子数2~20の複素環含有基で置換されていてもよく、
R1およびR2で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-NR3-、-NR3CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-またはCSO-で置換されていてもよく、
R3は、水素原子、炭素原子数1~20の炭化水素基を表し、
nは0または1を表し、*は結合手を表す。
前記オキシムエステル基を有さない光ラジカル開裂性基は、下記一般式(IVα)、(IVβ)、(IVγ)、(IVδ)、(IVε)、(IVζ)および(IVθ)で表される基である。
(一般式(IVα)~(IVθ)中、R31は、OR41、NR42R43または炭素原子数2~20の複素環含有基を表し、
R32およびR33は、R41またはOR41を表し、
R32とR33は結合して環を形成していてもよく、
R41は、水素原子または炭素原子数1~20の炭化水素基を表し、
R42およびR43は、炭素原子数1~20の炭化水素基を表し、
R71は、炭素原子数1~20の炭化水素基を表し、
R72およびR73は、R41またはOR41を表し、
R34、R35、R36、R37、R38、R39、R40、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6およびAr7は、炭素原子数6~20のアリール基を表し、
v1、v2、v3、v4、v5およびv6は、0または1を表し、v7は、1を表し、*は、結合手を表し、
R31中の前記複素環含有基は、窒素原子を有する。) - 下記一般式(II)で表される構造を有する請求項1記載のオキシムエステル化合物。
(一般式(II)中、A1は、炭素原子数6~20の芳香族環を表し、
R11は、前記一般式(I)で表される基を表し、
R12は、前記オキシムエステル基を有さない光ラジカル開裂性基、前記オキシムエステル基を有さない光ラジカル開裂性基で置換された炭素原子数1~20の炭化水素基、または前記オキシムエステル基を有さない光ラジカル開裂性基で置換された炭素原子数2~20の複素環含有基を表し、
R13は、それぞれ独立にハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基または炭素原子数2~20の複素環含有基を表し、
R12およびR13で表される基中の水素原子の1つまたは2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基または炭素原子数2~20の複素環含有基で置換されていてもよく、
R12およびR13で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-、-CO-、-COO-、-OCO-、-NR14-、-NR14CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-またはCSO-で置換されていてもよく、
R14は、水素原子、炭素原子数1~20の炭化水素基を表し、
aは1~20の整数を表し、aが2以上の整数の場合、複数存在するR11は、同一で
あっても異なっていてもよく、
bは1~20の整数を表し、bが2以上の整数の場合、複数存在するR12は、同一であっても異なっていてもよく、
cは0~20の整数を表し、cが2以上の整数の場合、複数存在するR13は、同一であっても異なっていてもよいが、
a+b+cは20以下である。) - A1が、下記一般式(IIIα)または(IIIβ)で表される構造である請求項2記載のオキシムエステル化合物。
(一般式(IIIα)中、X1は、酸素原子、硫黄原子、セレン原子、CR21R22、CO、NR23またはPR24を表し、
X2は、単結合、無結合、酸素原子、硫黄原子、セレン原子、CR21R22、CO、NR23またはPR24を表し、
R21、R22、R23およびR24は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基または複素環を含有する炭素原子数2~20の基を表し、R21、R22、R23およびR24で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアン基、水酸基、カルボキシル基または炭素原子数2~20の複素環基で置換されていてもよく、
R21、R22、R23およびR24で表される基中のメチレン基の1つまたは2つ以上は、酸素が隣り合わない条件で-O-に置換されていてもよい。)
- 前記一般式(II)中のR12が、前記オキシムエステル基を有さない光ラジカル開裂性基である請求項2または3記載のオキシムエステル化合物。
- 請求項1~4のうちいずれか一項記載のオキシムエステル化合物を含有することを特徴とする重合開始剤。
- 請求項5記載の重合開始剤(A)およびエチレン性不飽和化合物(B)を含有することを特徴とする重合性組成物。
- さらに、着色剤(C)を含有する請求項6記載の重合性組成物。
- 請求項6または7記載の重合性組成物より得られることを特徴とする硬化物。
- 請求項8記載の硬化物からなることを特徴とするカラーフィルタ。
- 請求項9に記載のカラーフィルタを備えてなることを特徴とする表示装置。
- 請求項6または7記載の重合性組成物に光照射をする工程、もしくは、請求項6または7記載の重合性組成物を加熱によって硬化させる工程を有することを特徴とする硬化物の製造方法。
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WO2020238862A1 (zh) * | 2019-05-30 | 2020-12-03 | 常州强力先端电子材料有限公司 | 芴类引发剂、包含其的光固化组合物及应用 |
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KR20220157365A (ko) * | 2020-03-24 | 2022-11-29 | 가부시키가이샤 아데카 | 화합물, 조성물, 경화물 및 경화물의 제조 방법 |
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JP2021161394A (ja) | 2020-03-31 | 2021-10-11 | 住友化学株式会社 | 硬化性樹脂組成物及び表示装置 |
JP2021161392A (ja) | 2020-03-31 | 2021-10-11 | 住友化学株式会社 | 硬化性樹脂組成物及び表示装置 |
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JP2022041900A (ja) | 2020-08-31 | 2022-03-11 | 住友化学株式会社 | 積層体及び表示装置 |
WO2022075452A1 (ja) * | 2020-10-08 | 2022-04-14 | 株式会社Adeka | 化合物、重合開始剤、重合性組成物、硬化物、カラーフィルタ及び硬化物の製造方法 |
EP4332123A1 (en) | 2021-04-28 | 2024-03-06 | Sumitomo Chemical Company Limited | Cured film and display device |
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WO2024004426A1 (ja) * | 2022-06-27 | 2024-01-04 | 富士フイルム株式会社 | 硬化性組成物、硬化物の製造方法、膜、光学素子、イメージセンサ、固体撮像素子、画像表示装置、及び、ラジカル重合開始剤 |
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TWI801619B (zh) | 2023-05-11 |
JPWO2020004601A1 (ja) | 2021-08-02 |
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WO2020004601A1 (ja) | 2020-01-02 |
CN112004800A (zh) | 2020-11-27 |
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