JPWO2020031986A1 - Carbamoyloxime compound and polymerization initiator and polymerizable composition containing the compound. - Google Patents
Carbamoyloxime compound and polymerization initiator and polymerizable composition containing the compound. Download PDFInfo
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- JPWO2020031986A1 JPWO2020031986A1 JP2020535773A JP2020535773A JPWO2020031986A1 JP WO2020031986 A1 JPWO2020031986 A1 JP WO2020031986A1 JP 2020535773 A JP2020535773 A JP 2020535773A JP 2020535773 A JP2020535773 A JP 2020535773A JP WO2020031986 A1 JPWO2020031986 A1 JP WO2020031986A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 146
- -1 Carbamoyloxime compound Chemical class 0.000 title claims abstract description 123
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000003505 polymerization initiator Substances 0.000 title claims abstract description 30
- 229960001330 hydroxycarbamide Drugs 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 125000001931 aliphatic group Chemical group 0.000 claims description 53
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000005011 phenolic resin Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000003822 epoxy resin Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 42
- 230000035945 sensitivity Effects 0.000 abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000002585 base Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
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- 230000015572 biosynthetic process Effects 0.000 description 18
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- 238000003786 synthesis reaction Methods 0.000 description 18
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- 150000002923 oximes Chemical class 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
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- 125000001424 substituent group Chemical group 0.000 description 14
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
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- 238000005192 partition Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
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- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
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- ALPIESLRVWNLAX-UHFFFAOYSA-N hexane-1,1-dithiol Chemical compound CCCCCC(S)S ALPIESLRVWNLAX-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001093 holography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 229910000457 iridium oxide Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-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
- 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
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003273 ketjen black Substances 0.000 description 1
- 125000000468 ketone group Chemical group 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
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 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
- 229960003151 mercaptamine Drugs 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- HTEAGOMAXMOFFS-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C HTEAGOMAXMOFFS-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 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
- 235000010755 mineral Nutrition 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000002116 nanohorn Substances 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical class 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
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 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
- 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
- 229920001778 nylon Polymers 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
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- ZKCXAZCRQJSFTQ-UHFFFAOYSA-N oxetane-2-carboxylic acid Chemical compound OC(=O)C1CCO1 ZKCXAZCRQJSFTQ-UHFFFAOYSA-N 0.000 description 1
- HCSAZRQAEVYJJH-UHFFFAOYSA-N oxetane-2-thiol Chemical compound SC1CCO1 HCSAZRQAEVYJJH-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 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
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- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 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
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 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
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001725 pyrenyl 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
- 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
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 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
- 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 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
- 238000005406 washing Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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Abstract
本発明の課題は、溶剤への溶解性が高く、且つ、満足できる感度(塩基発生能)を有する化合物、並びに、該化合物を重合開始剤として含有してなる重合性組成物及びその硬化物を提供することにある。本発明は、下記式(I)で表されるカルバモイルオキシム化合物を提供するものである。更に、本発明は、該化合物を含む重合開始剤、該重合開始剤及び重合性化合物を含有する重合性組成物、並びにその硬化物及びその製造方法を提供する。式中の符号の定義は明細書を参照。An object of the present invention is a compound having high solubility in a solvent and having a satisfactory sensitivity (base generation ability), a polymerizable composition containing the compound as a polymerization initiator, and a cured product thereof. To provide. The present invention provides a carbamoyloxime compound represented by the following formula (I). Furthermore, the present invention provides a polymerization initiator containing the compound, a polymerizable composition containing the polymerization initiator and the polymerizable compound, a cured product thereof, and a method for producing the same. Refer to the specification for the definition of the code in the formula.
Description
本発明は、重合性組成物に用いられる重合開始剤等として有用な化合物、重合性化合物に該化合物を含有させてなる重合性組成物、及び該重合性組成物の硬化物に関する。 The present invention relates to a compound useful as a polymerization initiator or the like used in a polymerizable composition, a polymerizable composition obtained by containing the compound in a polymerizable compound, and a cured product of the polymerizable composition.
一般に、感光性樹脂組成物等の重合性組成物は、感光性樹脂等の重合性化合物に光重合開始剤を加えたものであり、エネルギー線(光)照射により重合硬化、又は現像させることができるため、光硬化性インキ、感光性印刷版、各種フォトレジスト、光硬化性接着剤等に用いられている。 Generally, a polymerizable composition such as a photosensitive resin composition is obtained by adding a photopolymerization initiator to a polymerizable compound such as a photosensitive resin, and can be polymerized and cured or developed by irradiation with energy rays (light). Therefore, it is used in photocurable inks, photosensitive printing plates, various photoresists, photocurable adhesives, and the like.
光重合開始剤は、エネルギー線(光)照射により発生する活性種の違いで、光ラジカル発生剤、光酸発生剤、光塩基発生剤に分けられる。光ラジカル発生剤は、硬化速度が速く、硬化後に活性種が残存しない等の長所がある一方、酸素による硬化阻害が起こるため薄膜の硬化においては酸素を遮断する層等を設けなければならないという短所がある。光酸発生剤は、酸素による阻害を受けないという長所がある一方、活性種の酸が残存することで金属基板を腐食させたり、硬化後の樹脂を変性させたりする等の短所がある。光塩基発生剤は、前記の酸素による硬化阻害及び残存活性種による腐食といった問題を生じにくいため注目されているが、概して光酸発生剤と比較すると低感度(低硬化性)という問題があった。光塩基発生剤は、例えば特許文献1〜5等により開示されている。 Photopolymerization initiators are classified into photoradical generators, photoacid generators, and photobase generators, depending on the active species generated by energy ray (light) irradiation. The photoradical generator has advantages such as a high curing rate and no active species remaining after curing, but has a disadvantage that a layer or the like that blocks oxygen must be provided in the curing of the thin film because the curing is inhibited by oxygen. There is. The photoacid generator has an advantage that it is not inhibited by oxygen, but has a disadvantage that the residual active acid causes the metal substrate to corrode and the resin after curing is modified. Photobase generators are attracting attention because they are less likely to cause problems such as inhibition of curing by oxygen and corrosion by residual active species, but generally have a problem of low sensitivity (low curability) as compared with photoacid generators. .. Photobase generators are disclosed, for example, in Patent Documents 1 to 5.
しかしながら、従来の光塩基発生剤は、感度(塩基発生能)及び溶剤への溶解性の点で十分なものではない。
従って、本発明の目的は、溶剤への溶解性が高く、満足できる感度(塩基発生能)を有する化合物、該化合物を重合開始剤として含有してなる重合性組成物及びその硬化物を提供することにある。However, conventional photobase generators are not sufficient in terms of sensitivity (base generation ability) and solubility in a solvent.
Therefore, an object of the present invention is to provide a compound having high solubility in a solvent and having satisfactory sensitivity (base generation ability), a polymerizable composition containing the compound as a polymerization initiator, and a cured product thereof. There is.
本発明者は、鋭意検討を行い、特定の構造を有する化合物が重合開始剤として、高い感度(塩基発生能)を有することを知見した。 The present inventor conducted diligent studies and found that a compound having a specific structure has high sensitivity (base generation ability) as a polymerization initiator.
本発明は、下記式(I)で表されるカルバモイルオキシム化合物を提供することにより、上記目的を達成したものである。 The present invention has achieved the above object by providing a carbamoyloxime compound represented by the following formula (I).
R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ独立に、水素原子、シアノ基、ニトロ基、−OR11、−COOR11、−CO−R11、−SR11、ハロゲン原子、炭素原子数1〜20の脂肪族炭化水素基、炭素原子数6〜20の芳香族炭化水素基、炭素原子数2〜20の複素環を含有する基又は下記式(II)で表される基を表し、
R11は、炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基を表し、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10及びR11で表される基中の水素原子の1つ又は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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換される場合があり、
R3、R4、R5、R6、R7、R8、R9及びR10のうち一つ以上が下記式(II)で表される基である。
X1は、−NR22R23、下記式(a)又は下記式(b)で表される基であり、
R22及びR23は、それぞれ独立に、水素原子、炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基であるか、
R22とR23が、互いに連結して、窒素原子及び炭素原子からなる環、又は酸素原子、窒素原子及び炭素原子からなる環であり、
R21、R22及びR23で表される基中の水素原子の1つ又は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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換される場合があり、
nは、0又は1を表し、*は結合手を表す。
R31とR32、R33とR34、R35とR36、R37とR38及びR39とR40が、互いに連結して、窒素原子及び炭素原子からなる環、又は酸素原子、窒素原子及び炭素原子からなる環を形成する場合があり、
R31、R32、R33、R34、R35、R36、R37、R38、R39及びR40で表される基中の水素原子の1つ又は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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換される場合があり、
*は結合手を表す。
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently hydrogen atoms, cyano groups, nitro groups, -OR 11 , -COOR 11 , -CO-R, respectively. 11 , -SR 11 , halogen atom, aliphatic hydrocarbon group having 1 to 20 carbon atoms, aromatic hydrocarbon group having 6 to 20 carbon atoms, group containing a heterocycle having 2 to 20 carbon atoms, or the following Represents the group represented by equation (II)
R 11 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
One or more of the hydrogen atoms in the groups represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are halogens. Atomic, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group, isocyanate group or group containing a heterocycle having 2 to 20 carbon atoms. May be replaced with
One or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is a group represented by the following formula (II).
X 1 is −NR 22 R 23 , a group represented by the following formula (a) or the following formula (b).
Each of R 22 and R 23 is independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
R 22 and R 23 are connected to each other and are a ring composed of a nitrogen atom and a carbon atom, or a ring composed of an oxygen atom, a nitrogen atom and a carbon atom.
One or more of the hydrogen atoms in the groups represented by R 21 , R 22 and R 23 are halogen atoms, nitro groups, cyano groups, hydroxyl groups, amino groups, carboxyl groups, methacryloyl groups, acryloyl groups and epoxy groups. , Vinyl group, vinyl ether group, mercapto group, isocyanate group or group containing a heterocycle having 2 to 20 carbon atoms may be substituted.
n represents 0 or 1, and * represents a bond.
R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38, and R 39 and R 40 are connected to each other to form a ring consisting of nitrogen and carbon atoms, or an oxygen atom and nitrogen. May form a ring of atoms and carbon atoms,
One or more of the hydrogen atoms in the group represented by R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are halogen atoms, nitro. Substituted with a group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group or a group containing a heterocycle having 2 to 20 carbon atoms. May be
* Represents a bond.
また、本発明は、上記式(I)で表されるカルバモイルオキシム化合物を少なくとも1種含む潜在性塩基化合物を提供する。 The present invention also provides a latent base compound containing at least one carbamoyloxime compound represented by the above formula (I).
また、本発明は、上記式(I)で表されるカルバモイルオキシム化合物を少なくとも1種含む重合開始剤を提供する。 The present invention also provides a polymerization initiator containing at least one carbamoyloxime compound represented by the above formula (I).
また、本発明は、上記重合開始剤(A)及び重合性化合物(B)を含有する重合性組成物、及び、該重合性組成物から得られる硬化物を提供する。 The present invention also provides a polymerizable composition containing the above-mentioned polymerization initiator (A) and the polymerizable compound (B), and a cured product obtained from the polymerizable composition.
また、本発明は、上記重合性組成物にエネルギー線を照射する工程を有する硬化物の製造方法を提供する。 The present invention also provides a method for producing a cured product, which comprises a step of irradiating the polymerizable composition with energy rays.
本発明のカルバモイルオキシム化合物は、重合開始剤として用いた場合、従来の光塩基発生剤よりも効率的に塩基を発生させることができるため、低露光量においても重合性化合物を硬化させることができる。更に本発明のカルバモイルオキシム化合物は、溶剤への溶解性が高く、取り扱いが容易である。
また、本発明の重合性組成物は、低露光量において高い硬化性を示す。When the carbamoyloxime compound of the present invention is used as a polymerization initiator, it can generate a base more efficiently than a conventional photobase generator, so that the polymerizable compound can be cured even at a low exposure amount. .. Further, the carbamoyloxime compound of the present invention has high solubility in a solvent and is easy to handle.
Further, the polymerizable composition of the present invention exhibits high curability at a low exposure amount.
以下、本発明について、その好ましい実施形態について詳細に説明する。
本発明のカルバモイルオキシム化合物は、上記式(I)で表されるものである。式(I)で表されるカルバモイルオキシム化合物には、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。
即ち、本明細書において、上記式(I)で表されるカルバモイルオキシム化合物、並びに後述する該化合物の好ましい形態である化合物及び例示化合物は両方の混合物又はどちらか一方を表すものであり、異性体を示した構造に限定するものではない。以下、式(I)で表されるカルバモイルオキシム化合物を単に、「式(I)で表される化合物」又は「本発明の化合物」ともいう。
なお、式(I)中のR1〜R11、R21〜R23及びR31〜R40で表される基が、炭素原子を含む基により中断又は置換されている場合、それらの炭素原子数を含めた数が規定の炭素原子数となる。Hereinafter, the preferred embodiment of the present invention will be described in detail.
The carbamoyloxime compound of the present invention is represented by the above formula (I). The carbamoyl oxime compound represented by the formula (I) has geometric isomers due to the double bond of the oxime, but these are not distinguished.
That is, in the present specification, the carbamoyloxime compound represented by the above formula (I), and the compound and the exemplified compound which are preferable forms of the compound described later represent a mixture of both or one of them and are isomers. It is not limited to the structure shown in. Hereinafter, the carbamoyloxime compound represented by the formula (I) is also simply referred to as a "compound represented by the formula (I)" or a "compound of the present invention".
When the groups represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40 in the formula (I) are interrupted or substituted with a group containing a carbon atom, those carbon atoms The number including the number is the specified number of carbon atoms.
上記式(I)中のR1〜R11及びR21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基としては、無置換のものでは例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、s−ブチル、t−ブチル、アミル、イソアミル、t−アミル、ヘキシル、ヘプチル、オクチル、イソオクチル、2−エチルヘキシル、t−オクチル、ノニル、イソノニル、デシル、イソデシル、ウンデシル、ドデシル、テトラデシル、ヘキサデシル、オクタデシル、イコシル、シクロペンチル、シクロヘキシル、シクロヘキシルメチル等のアルキル基のほか、これらアルキル基の炭素−炭素一重結合の1つ以上を炭素−炭素二重結合又は炭素−炭素三重結合に変更してなる不飽和脂肪族炭化水素基等が挙げられる。これらの脂肪族炭化水素基は、基中のメチレン基の1つ又は2つ以上が、−O−、−COO−、−OCO−、−CO−、−CS−、−S−、−SO−、−SO2−、−NR−、−NR−CO−、−CO−NR−、−NR−COO−、−OCO−NR−又は−SiRR’−で置換される場合がある。但し、これら2価の基は隣り合わないものとする。
R及びR’は、水素原子又は脂肪族炭化水素基であり、R及びR’で表される脂肪族炭化水素基としては、例えばR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。 As the aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 11 and R 21 to R 23 and R 31 to R 40 in the above formula (I), for example, an unsubstituted one is used, for example. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, In addition to alkyl groups such as isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, cyclopentyl, cyclohexyl, and cyclohexylmethyl, one or more of the carbon-carbon single bonds of these alkyl groups are carbon-carbon double bonds or carbon-carbons. Examples thereof include an unsaturated aliphatic hydrocarbon group formed by changing to a carbon triple bond. In these aliphatic hydrocarbon groups, one or more of the methylene groups in the group are -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-. , -SO 2- , -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- or -SiRR'-may be replaced. However, these divalent groups shall not be adjacent to each other.
R and R'are hydrogen atoms or aliphatic hydrocarbon groups, and examples of the aliphatic hydrocarbon group represented by R and R'include R 1 to R 11 , R 21 to R 23 and R 31 to R. Examples thereof include groups similar to those exemplified as the aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by 40.
上記式(I)中のR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数6〜20の芳香族炭化水素基としては、無置換のものでは例えば、フェニル、ナフチル、フェナントリル、ピレニル及びビフェニル(以下まとめて「フェニル等」ともいう)、並びに脂肪族炭化水素基により置換されたフェニル等が挙げられ、これらの芳香族炭化水素基中のアルキル基部分又は芳香族環と脂肪族炭化水素基との結合部は、−O−、−COO−、−OCO−、−CO−、−CS−、−S−、−SO−、−SO2−、−NR−、−NR−CO−、−CO−NR−、−NR−COO−、−OCO−NR−又は−SiRR’−で中断されていてもよい。但し、これら中断する2価の基は隣り合わないものとする。
上記フェニル等を置換する脂肪族炭化水素基としては、上記のR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。 As the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40 in the above formula (I), for example, an unsubstituted one is used, for example. Examples thereof include phenyl, naphthyl, phenanthryl, pyrenyl and biphenyl (hereinafter collectively referred to as “phenyl and the like”), and phenyl substituted with an aliphatic hydrocarbon group, and the alkyl group portion in these aromatic hydrocarbon groups or The bond between the aromatic ring and the aliphatic hydrocarbon group is -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO 2- , -NR. -, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- or -SiRR'-may be interrupted. However, these interrupted divalent groups shall not be adjacent.
Examples of the aliphatic hydrocarbon group substituting phenyl and the like include the aliphatic hydrocarbon groups having 1 to 20 carbon atoms represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40. Groups similar to those illustrated can be mentioned.
R1〜R11、R21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基及びR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数6〜20の芳香族炭化水素基が置換基を有している場合、当該置換基を有している上記脂肪族炭化水素基及び上記芳香族炭化水素基としては、上記で説明した無置換体の水素原子がハロゲン原子、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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換されているものが挙げられる。当該炭素原子数2〜20の複素環を含有する基としては、後述するR3〜R10で表される無置換の炭素原子数2〜20の複素環を含有する基の例と同様のものが挙げられる。An aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40 , and R 1 to R 11 , R 21 to R 23 and R 31 to R. When the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by 40 has a substituent, the aliphatic hydrocarbon group having the substituent and the aromatic hydrocarbon group may be used. , The hydrogen atom of the substituent described above is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group or Examples thereof include those substituted with a group containing a heterocycle having 2 to 20 carbon atoms. The group containing the heterocycle having 2 to 20 carbon atoms is the same as the example of the group containing the heterocyclic ring having 2 to 20 carbon atoms, which is represented by R 3 to R 10 described later. Can be mentioned.
R3〜R11で表されるハロゲン原子並びにR1〜R11、R21〜R23及びR31〜R40で表される基中の水素原子が置換される場合のあるハロゲン原子としては、フッ素、塩素、臭素、ヨウ素の各原子が挙げられる。Halogen atoms represented by R 3 to R 11 and hydrogen atoms in the groups represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40 may be substituted as halogen atoms. Examples include fluorine, chlorine, bromine, and iodine atoms.
本発明において、「窒素原子及び炭素原子からなる環」とは、環の骨格を形成する原子が窒素原子及び炭素原子のみからなる環を意味する。また、「酸素原子、窒素原子及び炭素原子からなる環」とは、環の骨格を形成する原子が酸素原子、窒素原子及び炭素原子のみからなる環を意味する。
R22とR23、R31とR32、R33とR34、R35とR36、R37とR38及びR39とR40が互いに連結して形成する窒素原子及び炭素原子からなる環としては、結合している窒素原子を含めた基として、ピロール環、ピロリジン環、イミダゾール環、イミダゾリジン環、イミダゾリン環、ピラゾール環、ピラゾリジン環、ピペリジン環、ピペラジン環等(以下まとめて「ピロール環等」ともいう)のほか、これらピロール環等が脂肪族炭化水素基で置換された基が挙げられる。この脂肪族炭化水素基としては、上記のR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
これら窒素原子及び炭素原子からなる環における水素原子の1又は2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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基により置換されていてもよい。当該炭素原子数2〜20の複素環を含有する基としては、後述するR3〜R10で表される無置換の炭素原子数2〜20の複素環を含有する基の例と同様のものが挙げられる。In the present invention, the "ring consisting of nitrogen atom and carbon atom" means a ring in which the atom forming the skeleton of the ring consists only of nitrogen atom and carbon atom. Further, the "ring consisting of oxygen atom, nitrogen atom and carbon atom" means a ring in which the atom forming the skeleton of the ring consists only of oxygen atom, nitrogen atom and carbon atom.
A ring consisting of nitrogen and carbon atoms formed by connecting R 22 and R 23 , R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38, and R 39 and R 40 to each other. As a group containing a bonded nitrogen atom, a pyrrole ring, a pyrrolidine ring, an imidazole ring, an imidazolidine ring, an imidazoline ring, a pyrazole ring, a pyrazolidine ring, a piperidine ring, a piperazine ring, etc. Etc.), as well as groups in which these pyrrole rings and the like are substituted with aliphatic hydrocarbon groups. The aliphatic hydrocarbon group is the same as that exemplified as the above-mentioned aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40. The basis of.
One or more hydrogen atoms in the ring composed of nitrogen atom and carbon atom are halogen atom, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group and vinyl ether group. , A mercapto group, an isocyanate group or a group containing a heterocycle having 2 to 20 carbon atoms. The group containing the heterocycle having 2 to 20 carbon atoms is the same as the example of the group containing the heterocyclic ring having 2 to 20 carbon atoms, which is represented by R 3 to R 10 described later. Can be mentioned.
R22とR23、R31とR32、R33とR34、R35とR36、R37とR38及びR39とR40が互いに連結して形成する酸素原子、窒素原子及び炭素原子からなる環としては、結合している窒素原子を含めた基として、モルホリン環、オキサゾール環、オキサゾリン環、オキサジアゾール環等(以下まとめて「モルホリン環等」ともいう)のほか、これらモルホリン環等が脂肪族炭化水素基で置換された基も挙げられる。この脂肪族炭化水素基としては、上記のR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
これら酸素原子、窒素原子及び炭素原子からなる環等における水素原子の1又は2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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基により置換されていてもよい。
上記の炭素原子数2〜20の複素環を含有する基としては、後述するR3〜R10で表される無置換の炭素原子数2〜20の複素環を含有する基の例と同様のものが挙げられる。Oxygen atom, nitrogen atom and carbon atom formed by connecting R 22 and R 23 , R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38 and R 39 and R 40 to each other. The ring composed of a morpholine ring, an oxazole ring, an oxazoline ring, an oxaziazole ring, etc. (hereinafter collectively referred to as “morpholine ring, etc.”) as a group containing a bonded nitrogen atom, and these morpholine rings. There is also a group in which the above is substituted with an aliphatic hydrocarbon group. The aliphatic hydrocarbon group is the same as that exemplified as the above-mentioned aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40. The basis of.
One or two or more hydrogen atoms in the ring composed of oxygen atom, nitrogen atom and carbon atom are halogen atom, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group and vinyl. It may be substituted with a group, a vinyl ether group, a mercapto group, an isocyanate group, or a group containing a heterocycle having 2 to 20 carbon atoms.
The above-mentioned group containing a heterocycle having 2 to 20 carbon atoms is the same as the example of the group containing an unsubstituted heterocycle having 2 to 20 carbon atoms represented by R 3 to R 10 described later. Things can be mentioned.
上記式(I)中の、R3〜R10で表される炭素原子数2〜20の複素環を含有する基としては、無置換のものとして、テトラヒドロフラン基、ジオキソラニル基、テトラヒドロピラニル基、モルホリルフラン基、チオフェン基、メチルチオフェン基、ヘキシルチオフェン基、ベンゾチオフェン基、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、イミダゾリン基、ピラゾール基、ピラゾリジン基、ピペリジン基及びピペラジン基、並びに脂肪族炭化水素基で置換されたテトラヒドロフラン基、ジオキソラニル基、テトラヒドロピラニル基、モルホリルフラン基、チオフェン基、メチルチオフェン基、ヘキシルチオフェン基、ベンゾチオフェン基、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、ピラゾール基、ピラゾリジン基、ピペリジン基及びピペラジン基等(以下まとめて「テトラヒドロフラン基等」ともいう)、及び、これらテトラヒドロフラン基等が脂肪族炭化水素基で置換された基が挙げられる。この脂肪族炭化水素基としては、上記のR1〜R11、R21〜R23及びR31〜R40で表される炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
これらの複素環を含有する基中のアルキル基部分及び複素環と脂肪族炭化水素基との結合部は、−O−、−COO−、−OCO−、−CO−−CS−、−S−、−SO−、−SO2−、−NR−、−NR−CO−、−CO−NR−、−NR−COO−、−OCO−NR−又は−SiRR’−で中断されていてもよい。但し、これら中断する2価の基は隣り合わないものとする。なお、本明細書において、「炭素原子数2〜20の複素環を含有する基」における「2〜20」は、「複素環」ではなく「複素環を含有する基」の炭素原子数を規定する。In the above formula (I), the groups containing a heterocycle having 2 to 20 carbon atoms represented by R 3 to R 10 include a tetrahydrofuran group, a dioxolanyl group, and a tetrahydropyranyl group as unsubstituted groups. Morphorylfuran group, thiophene group, methylthiophene group, hexylthiophene group, benzothiophene group, pyrrole group, pyrrolidine group, imidazole group, imidazolidine group, imidazoline group, pyrazole group, pyrazolidine group, piperidine group and piperazine group, and fat Tetrahydrofuran group, dioxolanyl group, tetrahydropyranyl group, morpholylfuran group, thiophene group, methylthiophene group, hexylthiophene group, benzothiophene group, pyrrol group, pyrrolidine group, imidazole group, imidazolidine substituted with group hydrocarbon group Examples thereof include a group, a pyrazole group, a pyrazolidine group, a piperidine group, a piperazine group and the like (hereinafter collectively referred to as “tetrahydrofuran group and the like”), and a group in which these tetrahydrofuran groups and the like are substituted with an aliphatic hydrocarbon group. The aliphatic hydrocarbon group is the same as that exemplified as the above-mentioned aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 11 , R 21 to R 23 and R 31 to R 40. The basis of.
The alkyl group portion in the group containing these heterocycles and the bonding portion between the heterocycle and the aliphatic hydrocarbon group are -O-, -COO-, -OCO-, -CO-CS-, -S-. , -SO-, -SO 2- , -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- or -SiRR'-may be interrupted. However, these interrupted divalent groups shall not be adjacent. In the present specification, "2 to 20" in the "group containing a heterocycle having 2 to 20 carbon atoms" defines the number of carbon atoms of the "group containing a heterocycle" instead of the "heterocycle". do.
R3〜R10で表される炭素原子数2〜20の複素環を含有する基が置換基を有している場合、当該置換基を有している上記複素環を含有する基としては、上記で説明した無置換の複素環を含有する基の水素原子が、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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換されているものが挙げられる。When a group containing a heterocycle having 2 to 20 carbon atoms represented by R 3 to R 10 has a substituent, the group containing the heterocycle having the substituent is selected as the group containing the substituent. The hydrogen atom of the group containing the unsubstituted heterocycle described above is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, Examples thereof include those substituted with a mercapto group, an isocyanate group or a group containing a heterocycle having 2 to 20 carbon atoms.
上記式(I)で表される化合物の中でも、該式(I)中のX1が−NR22R23を表し、
R22及びR23が、それぞれ独立に、炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基であるか、
R22が水素原子であり、R23が炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基であるか、
R22とR23が、互いに連結して、窒素原子及び炭素原子からなる環、又は酸素原子、窒素原子及び炭素原子からなる環を形成している化合物は、重合開始剤として用いた場合、感度に優れることから好ましい。Among the compounds represented by the above formula (I), X 1 in the formula (I) represents −NR 22 R 23.
Whether R 22 and R 23 are independently aliphatic hydrocarbon groups having 1 to 20 carbon atoms or aromatic hydrocarbon groups having 6 to 20 carbon atoms, respectively.
Whether R 22 is a hydrogen atom and R 23 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
A compound in which R 22 and R 23 are linked to each other to form a ring composed of a nitrogen atom and a carbon atom or a ring composed of an oxygen atom, a nitrogen atom and a carbon atom is sensitive when used as a polymerization initiator. It is preferable because it is excellent in.
特に、上記式(I)中のX1が−NR22R23を表し、
R22とR23が、互いに連結して、窒素原子及び炭素原子からなる環を形成している化合物は、発生する塩基種の反応性が高いため重合開始剤として使用した場合、感度に優れることから好ましい。とりわけ、窒素原子及び炭素原子からなる環が5員環又は6員環であり、環に含まれる窒素原子数が1又は2である化合物が好ましい。
また、上記式(I)中のX1が−NR22R23を表し、
R22とR23が、それぞれ独立に、炭素原子数1〜20の脂肪族炭化水素基である化合物は、溶解性に優れるため好ましい、該炭化水素基は、炭素原子数1〜10のアルキル基が好ましい。
また、上記式(I)中のX1が−NR22R23を表し、
R22が水素原子であり、R23が炭素原子数6〜20の芳香族炭化水素基である化合物は、安定性に優れるため好ましい、該芳香族炭化水素基の炭素原子数は、炭素原子数1〜10であることが好ましい。該芳香族炭化水素基がフェニル基であることが好ましい。 In particular, X 1 in the above formula (I) represents −NR 22 R 23.
A compound in which R 22 and R 23 are linked to each other to form a ring composed of a nitrogen atom and a carbon atom has high reactivity of the generated base species, and therefore has excellent sensitivity when used as a polymerization initiator. Is preferable. In particular, a compound in which the ring composed of a nitrogen atom and a carbon atom is a 5-membered ring or a 6-membered ring and the number of nitrogen atoms contained in the ring is 1 or 2 is preferable.
Further, X 1 in the above formula (I) represents −NR 22 R 23.
A compound in which R 22 and R 23 are independently aliphatic hydrocarbon groups having 1 to 20 carbon atoms is preferable because it has excellent solubility. The hydrocarbon group is an alkyl group having 1 to 10 carbon atoms. Is preferable.
Further, X 1 in the above formula (I) represents −NR 22 R 23.
A compound in which R 22 is a hydrogen atom and R 23 is an aromatic hydrocarbon group having 6 to 20 carbon atoms is preferable because it has excellent stability. The carbon atom number of the aromatic hydrocarbon group is the number of carbon atoms. It is preferably 1 to 10. It is preferable that the aromatic hydrocarbon group is a phenyl group.
上記式(I)中のR3、R4、R5、R6、R7、R8、R9及びR10のうち2つ以上が上記式(II)で表される基である化合物は、重合開始剤として用いた場合、感度に優れ、得られる硬化物の残膜率が高いことから好ましく、R3、R4、R5、R6、R7、R8、R9及びR10のうち2〜3つが上記式(II)で表される基である化合物が、特に好ましい。The compound in which two or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 in the above formula (I) are the groups represented by the above formula (II) is When used as a polymerization initiator, it is preferable because it has excellent sensitivity and a high residual film ratio of the obtained cured product. R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 A compound in which two to three of them are groups represented by the above formula (II) is particularly preferable.
中でも、上記式(I)中のR3、R4、R5及びR6の少なくとも1つが上記式(II)で表される基であり、R7、R8、R9及びR10の少なくとも1つが上記式(II)で表される基である化合物が化合物の安定性が高いことから好ましい。とりわけ、上記式(I)中のR4又はR9が、上記式(II)で表される基である化合物は、化合物の安定性が高く、生産性に優れることから好ましく、上記式(I)中のR4及びR9が、上記式(II)で表される基である化合物が最も好ましい。Among them, at least one of R 3 , R 4 , R 5 and R 6 in the above formula (I) is a group represented by the above formula (II), and at least one of R 7 , R 8 , R 9 and R 10 A compound in which one is a group represented by the above formula (II) is preferable because the stability of the compound is high. In particular, a compound in which R 4 or R 9 in the above formula (I) is a group represented by the above formula (II) is preferable because the compound has high stability and excellent productivity, and the above formula (I). ), The compound in which R 4 and R 9 are the groups represented by the above formula (II) is most preferable.
上記式(I)中のR3、R4、R5、R6、R7、R8、R9及びR10のうち2つ以上が上記式(II)で表される基である場合、当該2以上の上記式(II)で表される基において、2つ以上存在するX1は同一であってもよく異なっていてもよい。前記の場合、2つ以上存在するR21は同一であってもよく異なっていてもよい。また2以上の上記式(II)で表される基におけるnは同一であってもよく異なっていてもよい。上記式(I)中のR3、R4、R5、R6、R7、R8、R9及びR10のうち2つ以上が上記式(II)で表される基である場合に、それら複数の式(II)で表される基におけるX1同士、R21同士及びn同士がそれぞれ同一であると生産性の点で好ましい。When two or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 in the above formula (I) are groups represented by the above formula (II), In the two or more groups represented by the above formula (II), two or more X 1s may be the same or different. In the above case, two or more R 21s may be the same or different. Further, n in two or more groups represented by the above formula (II) may be the same or different. When two or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 in the above formula (I) are groups represented by the above formula (II). , X 1 between the groups represented by the plurality of the formula (II), R 21 to each other and n together are preferred in terms of productivity and the same respectively.
更に、上記式(I)中のR3、R4、R5及びR6のうち、1つが上記式(II)で表される基であり、且つ、その他の3つがそれぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数1〜6の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数6〜12の芳香族炭化水素基である化合物は、感度が高い上に製造しやすい点で好ましく、R4及びR6のうち、1つが上記式(II)で表される基であり、且つ、その他並びにR3及びR5がそれぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数1〜6の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数6〜12の芳香族炭化水素基である化合物は、特に好ましい。
同様に、上記式(I)中のR7〜R10のうち、1つが上記式(II)で表される基であり、且つ、その他が水素原子、無置換若しくは置換基を有している炭素原子数1〜6の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数6〜12の芳香族炭化水素基である化合物は、感度が高い上に製造しやすい点で好ましい。 Further, of R 3 , R 4 , R 5 and R 6 in the above formula (I), one is a group represented by the above formula (II), and the other three are independently hydrogen atoms. , An aliphatic hydrocarbon group having 1 to 6 carbon atoms having an unsubstituted or substituent or an aromatic hydrocarbon group having 6 to 12 carbon atoms having an unsubstituted or substituent. It is preferable in that it has high sensitivity and is easy to manufacture, one of R 4 and R 6 is a group represented by the above formula (II), and the other and R 3 and R 5 are independent of each other. It is an aliphatic hydrocarbon group having 1 to 6 carbon atoms having a hydrogen atom, an unsubstituted or substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms having an unsubstituted or substituent. Compounds are particularly preferred.
Similarly, of R 7 to R 10 in the above formula (I), one is a group represented by the above formula (II), and the other has a hydrogen atom, an unsubstituted or substituent. Compounds that are aliphatic hydrocarbon groups having 1 to 6 carbon atoms or aromatic hydrocarbon groups having 6 to 12 carbon atoms having substituents or substituents are highly sensitive and easy to produce. preferable.
上記式(I)中のR3、R4、R5及びR6のうち、1つが上記式(II)で表される基であり、且つ、R7、R8、R9及びR10のうちの少なくとも1つが、水素原子、ニトロ基又は炭素原子数6〜12の芳香族炭化水素基、好ましくはニトロ基又は炭素原子数6〜12の芳香族炭化水素基である化合物、特にR7、R8、R9及びR10のうちの1つがニトロ基又は炭素原子数6〜12の芳香族炭化水素基である化合物は、感度が高い上に製造しやすい点で好ましい。該芳香族炭化水素基は無置換であってもよく、置換基を有していてもよいが、該芳香族炭化水素基はベンゾイル基が好ましい。 Of R 3 , R 4 , R 5 and R 6 in the above formula (I), one is a group represented by the above formula (II), and of R 7 , R 8 , R 9 and R 10 . at least one out but a hydrogen atom, a nitro group or an aromatic hydrocarbon group having 6 to 12 carbon atoms, the compound is preferably a nitro group or an aromatic hydrocarbon group having 6 to 12 carbon atoms, in particular R 7, A compound in which one of R 8 , R 9 and R 10 is a nitro group or an aromatic hydrocarbon group having 6 to 12 carbon atoms is preferable because of its high sensitivity and ease of production. The aromatic hydrocarbon group may be unsubstituted or has a substituent, but the aromatic hydrocarbon group is preferably a benzoyl group.
上記式(I)中のR4又はR9が、ニトロ基、トリフルオロメチル基又はベンゾイル基である化合物は、感度に優れることから好ましい。 A compound in which R 4 or R 9 in the above formula (I) is a nitro group, a trifluoromethyl group or a benzoyl group is preferable because it has excellent sensitivity.
R1及びR2で表される基は、互いに同一であってもよく、異なっていてもよいが、同一であることが、製造上容易である点で好ましい。The groups represented by R 1 and R 2 may be the same or different from each other, but it is preferable that they are the same because they are easy to manufacture.
上記式(I)中のR1及びR2が、炭素原子数2以上の脂肪族炭化水素基である化合物は、溶剤への溶解性に優れることから好ましく、炭素原子数2〜10の脂肪族炭化水素基が特に好ましい。
上記式(I)中のR1及びR2としては、脂肪族炭化水素基の中でも、溶剤への溶解性、感度及び透明性に優れることからアルキル基が好ましい。 Compounds in which R 1 and R 2 in the above formula (I) are aliphatic hydrocarbon groups having 2 or more carbon atoms are preferable because they are excellent in solubility in a solvent, and are preferred as aliphatic hydrocarbons having 2 to 10 carbon atoms. Hydrocarbon groups are particularly preferred.
Among the aliphatic hydrocarbon groups, R 1 and R 2 in the above formula (I) are preferably alkyl groups because they are excellent in solubility in a solvent, sensitivity and transparency.
上記式(I)中のR1及びR2が、炭素原子数1〜4の脂肪族炭化水素基である化合物も、溶剤への溶解性に優れることから好ましい。該脂肪族炭化水素基としては、溶剤への溶解性、感度及び透明性に優れることからアルキル基が好ましい。 A compound in which R 1 and R 2 in the above formula (I) are aliphatic hydrocarbon groups having 1 to 4 carbon atoms is also preferable because it has excellent solubility in a solvent. As the aliphatic hydrocarbon group, an alkyl group is preferable because it is excellent in solubility in a solvent, sensitivity and transparency.
R21が、炭素原子数2以上の脂肪族炭化水素基である化合物は、溶剤への溶解性に優れることから好ましく、感度に優れることから、炭素原子数2〜10の脂肪族炭化水素基が特に好ましい。
R21としては、脂肪族炭化水素基の中でも、溶剤への溶解性、感度及び透明性に優れることからアルキル基が好ましい。A compound in which R 21 is an aliphatic hydrocarbon group having 2 or more carbon atoms is preferable because it has excellent solubility in a solvent, and since it has excellent sensitivity, an aliphatic hydrocarbon group having 2 to 10 carbon atoms is preferable. Especially preferable.
Among the aliphatic hydrocarbon groups, the R 21 is preferably an alkyl group because it is excellent in solubility in a solvent, sensitivity and transparency.
式(II)中のnが0である化合物は、重合開始剤として用いた場合、熱に対する安定性が高いため好ましい。 The compound in which n in the formula (II) is 0 is preferable because it has high heat stability when used as a polymerization initiator.
式(II)中のnが1である化合物は、重合開始剤として用いた場合、低露光量で硬化するため好ましい。 The compound in which n is 1 in the formula (II) is preferable because it cures at a low exposure amount when used as a polymerization initiator.
上記式(I)で表される化合物の具体例としては、以下の化合物No.1〜No.54が挙げられる。但し、本発明は以下の化合物により何ら制限を受けるものではない。 Specific examples of the compound represented by the above formula (I) include the following compound Nos. 1-No. 54 is mentioned. However, the present invention is not limited by the following compounds.
上記式(I)で表される本発明のカルバモイルオキシム化合物は、特に限定されないが、n=0の場合、下記反応式1に従って、以下の方法により製造する方法が挙げられる。
即ち、公知であり、市販されているフルオレン化合物と酸クロリドとを塩化アルミニウム等のルイス酸の存在下で反応させることによりケトン化合物Aを得、ケトン化合物Aと塩酸ヒドロキシルアミンとをピリジン等の塩基の存在下に反応させることにより、オキシム化合物Aを得る。続いて、オキシム化合物Aに、クロロギ酸4-ニトロフェニルを反応させ、次いで該当するアミンを反応させることにより、上記式(I)で表されn=0である本発明のカルバモイルオキシム化合物Aを得る。The carbamoyloxime compound of the present invention represented by the above formula (I) is not particularly limited, but when n = 0, a method for producing by the following method according to the following reaction formula 1 can be mentioned.
That is, a known and commercially available fluorene compound and an acid chloride are reacted in the presence of a Lewis acid such as aluminum chloride to obtain a ketone compound A, and the ketone compound A and hydroxylamine hydrochloride are combined with a base such as pyridine. Oxime compound A is obtained by reacting in the presence of. Subsequently, 4-nitrophenyl chloroformate is reacted with the oxime compound A, and then the corresponding amine is reacted to obtain the carbamoyl oxime compound A of the present invention represented by the above formula (I) and having n = 0. ..
反応式1
n=1の場合は、下記反応式2に従い、公知であり、市販されているフルオレン化合物と酸クロリドとを塩化アルミニウム等のルイス酸の存在下で反応させることによりケトン化合物Bを得、酸性条件下でケトン体Bに亜硝酸イソブチルを反応させてオキシム化合物Bを得る。続いて、オキシム化合物Bに、クロロギ酸4-ニトロフェニルを反応させ、次いで該当するアミンを反応させることにより、上記式(I)で表されn=1である本発明のカルバモイルオキシム化合物Bを得る。 In the case of n = 1, a known and commercially available fluorene compound and an acid chloride are reacted in the presence of a Lewis acid such as aluminum chloride according to the following reaction formula 2 to obtain a ketone compound B under acidic conditions. The oxime compound B is obtained by reacting the ketone body B with isobutyl nitrite below. Subsequently, 4-nitrophenyl chloroformate is reacted with the oxime compound B, and then the corresponding amine is reacted to obtain the carbamoyl oxime compound B of the present invention represented by the above formula (I) and having n = 1. ..
反応式2
なお、ケトン体は、公知のものを使用してもよい。
また上記反応式1及び反応式2は何れもX1が−NR22R23の場合を示しているが、使用するアミンを変更することで、X1が式(a)又は式(b)で表される基である化合物も製造できる。
上記反応式1及び反応式2は何れもR4が式(II)で表される基である場合を示しているが、フルオレンにおいて別の位置に式(II)で表される基を導入する場合には、フルオレン環形成時にケトン基を導入する方法で得られる。
更に、例えば、R3、R4、R5、R6、R7、R8、R9及びR10のうち2つ以上が式(II)で表される基である化合物は、カルボニル基が、R3、R4、R5、R6、R7、R8、R9及びR10の2つ以上に結合しているジケトン体をケトン体として用いることで上記反応式1及び2と同様の方法にて製造できる。
オキシム化合物Aは、特許4223071号報に記載の方法でも製造できる。As the ketone body, a known ketone body may be used.
Further, both the reaction formula 1 and the reaction formula 2 show the case where X 1 is −NR 22 R 23 , but by changing the amine used, X 1 can be changed to the formula (a) or the formula (b). The compound that is the group represented can also be produced.
Although also R 4 both above Reaction Schemes 1 and 2 indicates a case where a group represented by Formula (II), to introduce a group represented by the formula (II) to a different position in the fluorene In some cases, it can be obtained by introducing a ketone group during fluorene ring formation.
Further, for example, a compound in which two or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are groups represented by the formula (II) has a carbonyl group. , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are the same as the above reaction formulas 1 and 2 by using a diketone body bonded to two or more as a ketone body. It can be manufactured by the method of.
Oxime compound A can also be produced by the method described in Japanese Patent No. 4223071.
本発明の化合物は、感光性樹脂の硬化性に優れる点、エネルギー線に対する感度が高い点から、以下で説明する光塩基発生剤である重合開始剤として好適に用いることができるほか、化学増幅型レジスト等に用いることができる。 The compound of the present invention can be suitably used as a polymerization initiator which is a photobase generator described below, and is also a chemically amplified type, because the photosensitive resin is excellent in curability and has high sensitivity to energy rays. It can be used as a resist or the like.
プロピレングリコール−1−モノメチルエーテル−2−アセテートへの25℃での溶解性が15%以上である化合物は、本発明の重合性組成物を作製する際に、多くの重合性化合物を選択できることから好ましい。なお、溶解性は後述する実施例に記載の方法にて測定できる。 A compound having a solubility in propylene glycol-1-monomethyl ether-2-acetate at 25 ° C. of 15% or more can be selected from many polymerizable compounds when preparing the polymerizable composition of the present invention. preferable. The solubility can be measured by the method described in Examples described later.
次に、本発明の潜在性塩基化合物、重合開始剤及び本発明の重合性組成物について説明する。なお、特に説明しない点については、本発明の化合物における説明が適宜適用される。 Next, the latent base compound of the present invention, the polymerization initiator, and the polymerizable composition of the present invention will be described. The description of the compound of the present invention is appropriately applied to points not particularly described.
<潜在性塩基化合物>
上記式(I)で表されるカルバモイルオキシム化合物は潜在性塩基化合物である。潜在性塩基化合物とは、紫外線等の光照射又は加熱によって塩基を発生する化合物であって、重合開始剤、塩基触媒、pH調整剤として使用することができる。操作性に優れることから光を照射することによって塩基を発生する光潜在性塩基化合物がより好ましい。<Latent base compound>
The carbamoyloxime compound represented by the above formula (I) is a latent base compound. The latent base compound is a compound that generates a base by irradiation with light such as ultraviolet rays or heating, and can be used as a polymerization initiator, a base catalyst, or a pH adjuster. A photolatent base compound that generates a base by irradiating with light is more preferable because of its excellent operability.
<重合開始剤(A)>
本発明の重合開始剤及び本発明の重合性組成物において、重合開始剤(A)は上記式(I)で表されるカルバモイルオキシム化合物を少なくとも1種含んでいるものである。本発明のカルバモイル化合物は、光の照射又は加熱によって効率的に塩基及びラジカルを発生することから、塩基発生剤及びラジカル重合開始剤として有用であり、特に塩基発生剤として有用である。<Polymerization initiator (A)>
In the polymerization initiator of the present invention and the polymerizable composition of the present invention, the polymerization initiator (A) contains at least one carbamoyloxime compound represented by the above formula (I). The carbamoyl compound of the present invention is useful as a base generator and a radical polymerization initiator because it efficiently generates bases and radicals by irradiation or heating with light, and is particularly useful as a base generator.
上記塩基発生剤及びラジカル重合開始剤の中でも、操作性に優れることから、光塩基発生剤及び光ラジカル重合開始剤として有用であり、特に光塩基発生剤として有用である。 Among the above-mentioned base generators and radical polymerization initiators, since they are excellent in operability, they are useful as photobase generators and photoradical polymerization initiators, and are particularly useful as photobase generators.
上記重合開始剤中における上記式(I)で表される化合物の含有量は、好ましくは1〜100質量%、より好ましくは50〜100質量%である。
本発明の重合性組成物において、重合開始剤(A)の含有量は、重合性化合物(B)100質量部に対して、好ましくは1〜20質量部、より好ましくは1〜10質量部である。重合開始剤(A)の含有量が、1質量部以上であることで、感度不足による硬化不良を防止しやすいため好ましく、20質量部以下とすることで、光照射時又は加熱時の揮発物を抑制できるため好ましい。The content of the compound represented by the above formula (I) in the polymerization initiator is preferably 1 to 100% by mass, more preferably 50 to 100% by mass.
In the polymerizable composition of the present invention, the content of the polymerization initiator (A) is preferably 1 to 20 parts by mass, more preferably 1 to 10 parts by mass with respect to 100 parts by mass of the polymerizable compound (B). be. The content of the polymerization initiator (A) is preferably 1 part by mass or more because it is easy to prevent curing failure due to insufficient sensitivity, and 20 parts by mass or less is preferable because it is a volatile substance during light irradiation or heating. Is preferable because it can suppress.
<重合性化合物(B)>
本発明で用いられる重合性化合物(B)としては、アニオン重合性官能基を有する化合物、塩基が触媒として作用する反応又は塩基が付加する反応により硬化する化合物、及びラジカル重合性化合物が挙げられ、紫外線等のエネルギー線を照射することにより重合して硬化する感光性樹脂又は硬化温度が低温化する硬化樹脂であることが好ましい。上記アニオン重合性官能基とは、紫外線等のエネルギー線によって光塩基発生剤から発生する塩基により重合しうる官能基を意味し、例えば、エポキシ基、エピスルフィド基、環状モノマー(σ−バレロラクトン、ε−カプロラクタム)、マロン酸エステル等が挙げられる。塩基が触媒として作用する反応又は塩基が付加する反応としては、イソシアネートとアルコールによるウレタン結合形成反応、エポキシ樹脂と水酸基を含有する化合物の付加反応、エポキシ樹脂とカルボン酸基を含有する化合物の付加反応、エポキシ樹脂とチオール化合物の付加反応、(メタ)アクリル基のマイケル付加反応、ポリアミック酸の脱水縮合反応、アルコキシシランの加水分解・重縮合反応等が挙げられる。<Polymerizable compound (B)>
Examples of the polymerizable compound (B) used in the present invention include a compound having an anionic polymerizable functional group, a compound that is cured by a reaction in which a base acts as a catalyst or a reaction in which a base is added, and a radically polymerizable compound. It is preferably a photosensitive resin that polymerizes and cures by irradiating with energy rays such as ultraviolet rays, or a cured resin that lowers the curing temperature. The anion-polymerizable functional group means a functional group that can be polymerized by a base generated from a photobase generator by an energy ray such as ultraviolet rays, and for example, an epoxy group, an episulfide group, or a cyclic monomer (σ-valerolactone, ε). -Caprolactam), malonic acid ester, etc. Reactions in which a base acts as a catalyst or a base is added include a urethane bond formation reaction between isocyanate and alcohol, an addition reaction between an epoxy resin and a compound containing a hydroxyl group, and an addition reaction between an epoxy resin and a compound containing a carboxylic acid group. , Addition reaction of epoxy resin and thiol compound, Michael addition reaction of (meth) acrylic group, dehydration condensation reaction of polyamic acid, hydrolysis / polycondensation reaction of alkoxysilane and the like.
アニオン重合性官能基を有する化合物としては例えば、エポキシ樹脂、オキセタン樹脂、エピスルフィド樹脂、環状アミド(ラクタム系化合物)、環状エステル(ラクトン系化合物)、環状カーボネート系化合物、マロン酸エステル等が挙げられる。塩基が触媒として作用する反応又は塩基が付加する反応により硬化する化合物としては、例えば、ポリアミド樹脂(脱水環化によるポリイミド化反応)、エポキシ・水酸基系(開環付加反応)、エポキシ・カルボン酸系(開環付加反応)、エポキシ・チオール系(開環付加反応)、エポキシ・酸無水物系(開環重縮合)、シアネートエステル(環化反応)、シアネートエステル・エポキシ系(環化反応)、シアネートエステル(環化反応)、シアネートエステル・マレイミド系(架橋共重合)、オキセタン・水酸基系(開環付加反応)、オキセタン・カルボン酸系(開環付加反応)、オキセタン・チオール系(開環付加反応)、オキセタン・酸無水物系(開環重縮合)、エピスルフィド・水酸基系(開環付加反応)、エピスルフィド・カルボン酸系(開環付加反応)、エピスルフィド・チオール系(開環付加反応)、エピスルフィド・酸無水物系(開環重縮合)アクリル・チオール系(マイケル付加反応)、メタクリル・チオール系(マイケル付加反応)、アクリル・アミン系(マイケル付加反応)、メタクリル・アミン系(マイケル付加反応)、カルボン酸・水酸基系(ポリエステル化反応)、カルボン酸・アミン系(ポリアミド化反応)、イソシアネート・水酸基系(ポリウレタン化反応)、アルコキシシラン系(加水分解・重縮合)等が挙げられる。ラジカルにより重合する化合物としては、エチレン性不飽和化合物が挙げられる。反応性が高いことからラジカル重合する化合物を使用することが好ましい。これらの樹脂は単独で用いてもよく、2種以上を併用してもよい。好ましい組合せとして、速やかに反応が進行することや接着性が良好であるという点から、エポキシ樹脂とフェノール樹脂の組合せ、低温硬化性に優れることから、エポキシ樹脂とチオール化合物の組合せ、反応性が高いことからエチレン性不飽和化合物とチオール化合物の組合せが挙げられる。 Examples of the compound having an anionic polymerizable functional group include epoxy resin, oxetane resin, episulfide resin, cyclic amide (lactam compound), cyclic ester (lactone compound), cyclic carbonate compound, malonic acid ester and the like. Examples of compounds that are cured by a reaction in which a base acts as a catalyst or a reaction in which a base is added include a polyamide resin (polynitation reaction by dehydration cyclization), an epoxy / hydroxyl group (ring-opening addition reaction), and an epoxy / carboxylic acid system. (Ring-opening addition reaction), epoxy-thiol-based (ring-opening addition reaction), epoxy-acid anhydride-based (ring-opening polycondensation), cyanate ester (cyclization reaction), cyanate ester-epoxy-based (cyclization reaction), Cyanate ester (cyclization reaction), cyanate ester / maleimide system (bridge copolymerization), oxetane / hydroxyl group system (ring-opening addition reaction), oxetane-carboxylic acid system (ring-opening addition reaction), oxetane-thiol system (ring-opening addition reaction) Reaction), oxetane / acid anhydride system (ring-opening polycondensation), episulfide / hydroxyl group (ring-opening addition reaction), episulfide-carboxylic acid system (ring-opening addition reaction), episulfide-thiol system (ring-opening addition reaction), Episulfide / acid anhydride type (ring-opening polycondensation) acrylic thiol type (Michael addition reaction), methacryl-thiol type (Michael addition reaction), acrylic amine type (Michael addition reaction), methacryl amine type (Michael addition reaction) ), Carous acid / hydroxyl type (polyesterization reaction), carboxylic acid / amine type (polyamide formation reaction), isocyanate / hydroxyl type (polyurization reaction), alkoxysilane type (hydrolysis / polycondensation) and the like. Examples of the compound polymerized by radicals include ethylenically unsaturated compounds. Since it has high reactivity, it is preferable to use a compound that undergoes radical polymerization. These resins may be used alone or in combination of two or more. As a preferable combination, a combination of an epoxy resin and a phenol resin is excellent in that the reaction proceeds quickly and the adhesiveness is good, and a combination of an epoxy resin and a thiol compound and a high reactivity because of excellent low-temperature curability. Therefore, a combination of an ethylenically unsaturated compound and a thiol compound can be mentioned.
上記エポキシ樹脂としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルクシノール等の単核多価フェノール化合物のポリグリシジルエーテル化合物;ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール(ビスフェノールF)、メチレンビス(オルトクレゾール)、エチリデンビスフェノール、イソプロピリデンビスフェノール(ビスフェノールA)、4,4’−ジヒドロキシベンゾフェノン、イソプロピリデンビス(オルトクレゾール)、テトラブロモビスフェノールA、1,3−ビス(4−ヒドロキシクミルベンゼン)、1,4−ビス(4−ヒドロキシクミルベンゼン)、1,1,3−トリス(4−ヒドロキシフェニル)ブタン、1,1,2,2−テトラ(4−ヒドロキシフェニル)エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物のポリグリシジルエーテル化合物;エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、ポリグリコール、チオジグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ソルビトール、ビスフェノールA−エチレンオキシド付加物等の多価アルコール類のポリグリシジルエーテル;マレイン酸、フマル酸、イタコン酸、コハク酸、グルタル酸、スベリン酸、アジピン酸、アゼライン酸、セバシン酸、ダイマー酸、トリマー酸、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、エンドメチレンテトラヒドロフタル酸等の脂肪族、芳香族又は脂環族多塩基酸のグリシジルエステル類、及びグリシジルメタクリレートの単独重合体又は共重合体;N,N−ジグリシジルアニリン、ビス(4−(N−メチル−N−グリシジルアミノ)フェニル)メタン、ジグリシジルオルトトルイジン等のグリシジルアミノ基を有するエポキシ化合物;ビニルシクロヘキセンジエポキシド、ジシクロペンタンジエンジエポキサイド、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、3,4−エポキシ−6−メチルシクロヘキシルメチル−6−メチルシクロヘキサンカルボキシレート、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート等の環状オレフィン化合物のエポキシ化物;エポキシ化ポリブタジエン、エポキシ化アクリロニトリル−ブタジエン共重合物、エポキシ化スチレン−ブタジエン共重合物等のエポキシ化共役ジエン重合体、トリグリシジルイソシアヌレート等の複素環化合物が挙げられる。また、これらのエポキシ樹脂は末端イソシアネートのプレポリマーによって内部架橋されたもの或いは多価の活性水素化合物(多価フェノール、ポリアミン、カルボニル基含有化合物、ポリリン酸エステル等)で高分子量化したものでもよい。
上記エポキシ樹脂の中では、硬化性に優れる点から、グリシジル基を有するものが好ましく、2官能以上のグリシジル基を有するものがより好ましい。Examples of the epoxy resin include polyglycidyl ether compounds of mononuclear polyvalent phenol compounds such as hydroquinone, resorcin, pyrocatechol, and fluoroglucosinol; dihydroxynaphthalene, biphenol, methylenebisphenol (bisphenol F), and methylenebis (orthocresol). , Echilidene bisphenol, isopropyridene bisphenol (bisphenol A), 4,4'-dihydroxybenzophenone, isopropyridenebis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene), 1,4 -Bis (4-hydroxycumylbenzene), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-hydroxyphenyl) ethane, thiobisphenol, sulfobisphenol, oxy Polyglycidyl ether compounds of polynuclear polyvalent phenolic compounds such as bisphenol, phenol novolac, orthocresol novolac, ethylphenol novolac, butylphenol novolac, octylphenol novolac, resorcin novolac, terpenphenol; ethylene glycol, propylene glycol, butylene glycol, hexanediol, poly Polyglycidyl ethers of polyhydric alcohols such as glycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-ethylene oxide adduct; maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberin Acids, adipic acid, azelaic acid, sebacic acid, dimer acid, trimeric acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, endomethylenetetrahydrophthalic acid Glycidyl esters of aliphatic, aromatic or alicyclic polybasic acids such as acids, and homopolymers or copolymers of glycidyl methacrylate; N, N-diglycidylaniline, bis (4- (N-methyl-N) -Epoxy compounds having a glycidylamino group such as glycidylamino) phenyl) methane, diglycidyl orthotoluidine; vinylcyclohexene diepoxide, dicyclopentanediene diepoxiside, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate. , 3,4-Epoxy-6-methylcyclo Epoxides of cyclic olefin compounds such as hexylmethyl-6-methylcyclohexanecarboxylate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate; epoxidized polybutadiene, epoxidized acrylonitrile-butadiene copolymer, epoxidized styrene Examples include epoxidized conjugated diene polymers such as butadiene copolymers and heterocyclic compounds such as triglycidyl isocyanurate. Further, these epoxy resins may be internally crosslinked with a prepolymer of a terminal isocyanate or have a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). ..
Among the above epoxy resins, those having a glycidyl group are preferable, and those having a bifunctional or higher functional glycidyl group are more preferable, from the viewpoint of excellent curability.
上記フェノール樹脂としては、1分子中に2個以上のヒドロキシ基を有するフェノール樹脂が好ましく、一般に公知のものを用いることができる。フェノール樹脂としては、例えば、ビスフェノールA型フェノール樹脂、ビスフェノールE型フェノール樹脂、ビスフェノールF型フェノール樹脂、ビスフェノールS型フェノール樹脂、フェノールノボラック樹脂、ビスフェノールAノボラック型フェノール樹脂、グリシジルエステル型フェノール樹脂、アラルキルノボラック型フェノール樹脂、ビフェニルアラルキル型フェノール樹脂、クレゾールノボラック型フェノール樹脂、多官能フェノール樹脂、ナフトール樹脂、ナフトールノボラック樹脂、多官能ナフトール樹脂、アントラセン型フェノール樹脂、ナフタレン骨格変性ノボラック型フェノール樹脂、フェノールアラルキル型フェノール樹脂、ナフトールアラルキル型フェノール樹脂、ジシクロペンタジエン型フェノール樹脂、ビフェニル型フェノール樹脂、脂環式フェノール樹脂、ポリオール型フェノール樹脂、リン含有フェノール樹脂、重合性不飽和炭化水素基含有フェノール樹脂及び、水酸基含有シリコーン樹脂類が挙げられるが、特に制限されるものではない。これらのフェノール樹脂は、1種を単独で又は2種以上を組合せて用いることができる。 As the phenol resin, a phenol resin having two or more hydroxy groups in one molecule is preferable, and generally known ones can be used. Examples of the phenol resin include bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolac resin, bisphenol A novolac type phenol resin, glycidyl ester type phenol resin, and aralkyl novolac. Type phenol resin, biphenyl aralkyl type phenol resin, cresol novolac type phenol resin, polyfunctional phenol resin, naphthol resin, naphthol novolac resin, polyfunctional naphthol resin, anthracene type phenol resin, naphthalene skeleton modified novolac type phenol resin, phenol aralkyl type phenol Resin, naphthol aralkyl type phenol resin, dicyclopentadiene type phenol resin, biphenyl type phenol resin, alicyclic phenol resin, polyol type phenol resin, phosphorus-containing phenol resin, polymerizable unsaturated hydrocarbon group-containing phenol resin, and hydroxyl group-containing Examples thereof include silicone resins, but the present invention is not particularly limited. These phenol resins can be used alone or in combination of two or more.
上記チオール化合物は特に制限されず、すべてのチオール化合物を包含するが、1分子中に2個以上のチオール基を有するものが好ましい。
チオール化合物の好ましい具体例としては、ビス(2−メルカプトエチル)スルフィド、2,5−ジメルカプトメチル−1,4−ジチアン、1,3−ビス(メルカプトメチル)ベンゼン、1,4−ビス(メルカプトメチル)ベンゼン、4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタン、4,8−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカン、4,7−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカン、5,7−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカン、1,2,6,7−テトラメルカプト−4−チアヘプタン、ペンタエリスリチオール、1,1,3,3−テトラキス(メルカプトメチルチオ)プロパン、ペンタエリスリトールテトラキスメルカプトプロピオネート、ペンタエリスリトールテトラキスチオグリコレート、トリメチロールプロパントリスチオグリコレート、及びトリメチロールプロパントリスメルカプトプロピオネートであり、より好ましくは、1,2,6,7−テトラメルカプト−4−チアヘプタン、ペンタエリスリチオール、ビス(2−メルカプトエチル)スルフィド、2,5−ビス(2−メルカプトメチル)−1,4−ジチアン、4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタン、1,3−ビス(メルカプトメチル)ベンゼン、ペンタエリスリトールテトラキスメルカプトプロピオネート、及びペンタエリスリトールテトラキスチオグリコレートが挙げられる。
特に好ましい化合物は、1,2,6,7−テトラメルカプト−4−チアヘプタン、ペンタエリスリチオール、ビス(2−メルカプトエチル)スルフィド、2,5−ジメルカプトメチル−1,4−ジチアン、及び4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタンである。
チオール化合物は1種を単独で又は2種以上を組合せて用いることができる。 The thiol compound is not particularly limited and includes all thiol compounds, but those having two or more thiol groups in one molecule are preferable.
Preferred specific examples of the thiol compound include bis (2-mercaptoethyl) sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 1,3-bis (mercaptomethyl) benzene, and 1,4-bis (mercapto). Methyl) benzene, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,7-di Mercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 1,2,6,7 -Tetramercapto-4-thiaheptan, pentaerythrithiol, 1,1,3,3-tetrakis (mercaptomethylthio) propane, pentaerythritol tetrakis mercaptopropionate, pentaerythritol tetrakisthioglycolate, trimethylolpropane tristhioglycolate , And trimethylolpropanthris mercaptopropionate, more preferably 1,2,6,7-tetramercapto-4-thiaheptan, pentaerythrithiol, bis (2-mercaptoethyl) sulfide, 2,5-. Bis (2-mercaptomethyl) -1,4-dithiane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 1,3-bis (mercaptomethyl) benzene, pentaerythritol tetrakis mercaptopropionate, And pentaerythritol tetrakisthioglycolate.
Particularly preferred compounds are 1,2,6,7-tetramercapto-4-thiaheptan, pentaerythrithiol, bis (2-mercaptoethyl) sulfide, 2,5-dimercaptomethyl-1,4-dithiane, and 4 -Mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.
The thiol compound may be used alone or in combination of two or more.
上記ポリアミド樹脂としては、酸二無水物としてはエチレンテトラカルボン酸二無水物、1,2,3,4−ベンゼンテトラカルボン酸二無水物、1,2,3,4−シクロヘキサンテトラカルボン酸二無水物、2,2’,3,3’−ベンゾフェノンテトラカルボン酸二無水物、2,2,3,3−ビフェニルテトラカルボン酸無水物、1,4,5,8−ナフタレンテトラカルボン酸二無水物、ジアミンとしては、(o−,m−若しくはp−)フェニレンジアミン、(3,3’−若しくは4,4’−)ジアミノジフェニルエーテル、ジアミノベンゾフェノンノン、(3,3’−若しくは4,4’−)ジアミノジフェニルメタン等を原料とする樹脂が挙げられる。 The polyamide resin includes ethylenetetracarboxylic dianhydride, 1,2,3,4-benzenetetracarboxylic dianhydride, and 1,2,3,4-cyclohexanetetracarboxylic dianhydride as acid dianhydride. , 2,2', 3,3'-benzophenonetetracarboxylic dianhydride, 2,2,3,3-biphenyltetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride As the diamine, (o-, m- or p-) phenylenediamine, (3,3'-or 4,4'-) diaminodiphenyl ether, diaminobenzophenonone, (3,3'-or 4,4'- ) Examples thereof include resins made from diaminodiphenylmethane or the like.
上記ポリウレタン樹脂としては、ジイソシアネートとして、トリレンジイソシアネート、ヘキサメチレンジイソシアネート、ジフェニルメタンジイソシアネート、イソホロンジイソシアネート等の多官能イソシアネートと、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオール等のポリオール(多官能アルコール)とを原料とする樹脂等が挙げられる。
また、上記ナイロン樹脂としては、ε−カプロラクタム、ラウリルラクタム等の環状モノマーを原料とした樹脂等が挙げられる。
また、上記ポリエステル樹脂としては、δ−バレロラクトン、β―プロピオラクトン等の環状モノマーを原料とした樹脂等が挙げられる。The polyurethane resin is made from a polyfunctional isocyanate such as tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, or isophorone diisocyanate, and a polyol (polyfunctional alcohol) such as a polyether polyol, a polyester polyol, or a polycarbonate polyol. Examples include resins to be used.
Examples of the nylon resin include resins made from cyclic monomers such as ε-caprolactam and lauryl lactam.
Examples of the polyester resin include resins made from cyclic monomers such as δ-valerolactone and β-propiolactone.
上記エチレン性不飽和化合物としては、例えば、エチレン、プロピレン、ブチレン、イソブチレン、塩化ビニル、塩化ビニリデン、フッ化ビニリデン、テトラフルオロエチレン等の不飽和脂肪族炭化水素;(メタ)アクリル酸、α―クロルアクリル酸、イタコン酸、マレイン酸、シトラコン酸、フマル酸、ハイミック酸、クロトン酸、イソクロトン酸、ビニル酢酸、アリル酢酸、桂皮酸、ソルビン酸、メサコン酸、コハク酸モノ[2−(メタ)アクリロイロキシエチル]、フタル酸モノ[2−(メタ)アクリロイロキシエチル]、ω−カルボキシポリカプロラクトンモノ(メタ)アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート;ヒドロキシエチル(メタ)アクリレート・マレート、ヒドロキシプロピル(メタ)アクリレート・マレート、ジシクロペンタジエン・マレート或いは1個のカルボキシル基と2個以上の(メタ)アクリロイル基とを有する多官能(メタ)アクリレート等の不飽和多塩基酸;(メタ)アクリル酸−2−ヒドロキシエチル、(メタ)アクリル酸−2−ヒドロキシプロピル、(メタ)アクリル酸グリシジル、下記アクリル化合物No.1〜No.4、(メタ)アクリル酸メチル、(メタ)アクリル酸ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸−t−ブチル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸イソオクチル、(メタ)アクリル酸イソノニル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸ジメチルアミノメチル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸アミノプロピル、(メタ)アクリル酸ジメチルアミノプロピル、(メタ)アクリル酸エトキシエチル、(メタ)アクリル酸ポリ(エトキシ)エチル、(メタ)アクリル酸ブトキシエトキシエチル、(メタ)アクリル酸エチルヘキシル、(メタ)アクリル酸フェノキシエチル、(メタ)アクリル酸テトラヒドロフリル、(メタ)アクリル酸ビニル、(メタ)アクリル酸アリル、(メタ)アクリル酸ベンジル、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリシクロデカンジメチロールジ(メタ)アクリレート、トリ[(メタ)アクリロイルエチル]イソシアヌレート、ポリエステル(メタ)アクリレートオリゴマー等の不飽和一塩基酸及び多価アルコール又は多価フェノールのエステル;(メタ)アクリル酸亜鉛、(メタ)アクリル酸マグネシウム等の不飽和多塩基酸の金属塩;マレイン酸無水物、イタコン酸無水物、シトラコン酸無水物、メチルテトラヒドロ無水フタル酸、テトラヒドロ無水フタル酸、トリアルキルテトラヒドロ無水フタル酸、5−(2,5−ジオキソテトラヒドロフリル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸−無水マレイン酸付加物、ドデセニル無水コハク酸、無水メチルハイミック酸等の不飽和多塩基酸の酸無水物;(メタ)アクリルアミド、メチレンビス−(メタ)アクリルアミド、ジエチレントリアミントリス(メタ)アクリルアミド、キシリレンビス(メタ)アクリルアミド、α−クロロアクリルアミド、N−2−ヒドロキシエチル(メタ)アクリルアミド等の不飽和一塩基酸及び多価アミンのアミド;アクロレイン等の不飽和アルデヒド;(メタ)アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデン、シアン化アリル等の不飽和ニトリル;スチレン、4−メチルスチレン、4−エチルスチレン、4−メトキシスチレン、4−ヒドロキシスチレン、4−クロロスチレン、ジビニルベンゼン、ビニルトルエン、ビニル安息香酸、ビニルフェノール、ビニルスルホン酸、4−ビニルベンゼンスルホン酸、ビニルベンジルメチルエーテル、ビニルベンジルグリシジルエーテル等の不飽和芳香族化合物;メチルビニルケトン等の不飽和ケトン;ビニルアミン、アリルアミン、N−ビニルピロリドン、ビニルピペリジン等の不飽和アミン化合物;アリルアルコール、クロチルアルコール等のビニルアルコール;ビニルメチルエーテル、ビニルエチルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル、アリルグリシジルエーテル等のビニルエーテル;マレイミド、N−フェニルマレイミド、N−シクロヘキシルマレイミド等の不飽和イミド類;インデン、1−メチルインデン等のインデン類;1,3−ブタジエン、イソプレン、クロロプレン等の脂肪族共役ジエン類;ポリスチレン、ポリメチル(メタ)アクリレート、ポリ−n−ブチル(メタ)アクリレート、ポリシロキサン等の重合体分子鎖の末端にモノ(メタ)アクリロイル基を有するマクロモノマー類;ビニルクロリド、ビニリデンクロリド、ジビニルスクシナート、ジアリルフタラート、トリアリルホスファート、トリアリルイソシアヌラート、ビニルチオエーテル、ビニルイミダゾール、ビニルオキサゾリン、ビニルカルバゾール、ビニルピロリドン、ビニルピリジン、水酸基含有ビニルモノマー及びポリイソシアネート化合物のビニルウレタン化合物、水酸基含有ビニルモノマー及びポリエポキシ化合物のビニルエポキシ化合物が挙げられる。
エチレン性不飽和化合物は、単独で又は2種以上を混合して使用することができる。Examples of the ethylenically unsaturated compound include unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, vinylidene fluoride, and tetrafluoroethylene; (meth) acrylic acid and α-chloro. Acrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, sorbic acid, mesaconic acid, mono [2- (meth) acrylloy Roxyethyl], mono (meth) acrylicyloxyethyl phthalate, ω-carboxypolycaprolactone mono (meth) acrylate, etc. Polymer mono (meth) acrylate having carboxy groups and hydroxyl groups at both ends; hydroxy Non-functional (meth) acrylates such as ethyl (meth) acrylate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate or polyfunctional (meth) acrylate having one carboxyl group and two or more (meth) acryloyl groups. Saturated polybasic acid; -2-hydroxyethyl (meth) acrylate, -2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, the following acrylic compound No. 1-No. 4. Methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, -t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, Aminopropyl (Meta) Acrylate, Dimethylaminopropyl (Meta) Acrylate, ethoxyethyl (Meta) Acrylate, Poly (ethoxy) Ethyl (Meta) Acrylate, Butoxyethoxyethyl (Meta) Acrylate, (Meta) ) Ethylhexyl acrylate, phenoxyethyl (meth) acrylate, tetrahydrofuryl (meth) acrylate, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, Diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol Di (meth) acrylate, trimethylol ethanetri (meth) acrylate, trimethylol propanthry (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol tetra (meth) acrylate, Unsaturated monobasic acids such as pentaerythritol tri (meth) acrylate, tricyclodecanedimethylol di (meth) acrylate, tri [(meth) acryloyl ethyl] isocyanurate, polyester (meth) acrylate oligomer, and polyhydric alcohols or polyvalents. Esters of phenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate, magnesium (meth) acrylate; maleic acid anhydride, itaconic acid anhydride, citraconic acid anhydride, methyltetrahydrophthalic anhydride, tetrahydro Acrylate, TrialkyltetrahydroAcrylate, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride, trialkyltetrahydrophthaliclate-male anhydride Acid anhydrides of unsaturated polybasic acids such as phosphate adducts, dodecenyl anhydride succinic acid, methylhymic anhydride; (meth) acrylamide, methylenebis- (meth) acrylamide, diethylenetriaminetris (meth) acrylamide, xylylenebis (meth) Unsaturated monobasic acids such as acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; unsaturated aldehydes such as achlorine; (meth) acrylonitrile, α-chloroacrylonitrile, cyanide Unsaturated nitriles such as vinylidene and allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinyl benzoic acid, vinylphenol , Vinyl sulfonic acid, 4-vinylbenzene sulfonic acid, vinylbenzyl methyl ether, vinylbenzyl glycidyl ether and other unsaturated aromatic compounds; unsaturated ketones such as methyl vinyl ketone; vinylamine, allylamine, N-vinylpyrrolidone, vinylpiperidin and the like. Unsaturated amine compounds; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether and allyl glycidyl ether; maleimide, N-phenylmaleimide, N-cyclohexyl Unsaturated imides such as maleimide; indens such as inden and 1-methylinden; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; polystyrene, polymethyl (meth) acrylate, poly-n-butyl ( Macromonomonics having a mono (meth) acryloyl group at the end of polymer molecular chains such as meta) acrylates and polysiloxanes; vinyl chlorides, vinylidene chlorides, divinylsuccinates, diallylphthalates, triallyl phosphates, triallyl isothias Examples thereof include nurate, vinylthioether, vinylimidazole, vinyloxazoline, vinylcarbazole, vinylpyrrolidone, vinylpyridine, a vinylurethane compound of a hydroxyl group-containing vinyl monomer and a polyisocyanate compound, and a vinyl epoxy compound of a hydroxyl group-containing vinyl monomer and a polyepoxy compound.
The ethylenically unsaturated compound can be used alone or in combination of two or more.
上記エチレン性不飽和化合物としては、市販品を用いることもでき、例えば、カヤラッドDPHA、DPEA−12、PEG400DA、THE−330、RP−1040、NPGDA、PET30、R−684(以上、日本化薬製);アロニックスM−215、M−350(以上、東亞合成製);NKエステルA−DPH、A−TMPT、A−DCP、A−HD−N、TMPT、DCP、NPG及びHD−N(以上、新中村化学工業製);SPC−1000、SPC−3000(以上、昭和電工製);等が挙げられる。 Commercially available products can also be used as the ethylenically unsaturated compound. For example, Kayarad DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, PET30, R-684 (all manufactured by Nippon Kayaku). ); Aronix M-215, M-350 (above, manufactured by Toagosei); NK ester A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG and HD-N (above, Shin-Nakamura Chemical Industry Co., Ltd.); SPC-1000, SPC-3000 (all manufactured by Showa Denko); etc.
重合性組成物(B)の含有量は、その使用目的に応じて適した量であればよいが、硬化不良を防ぐため、重合性組成物中の固形分(溶剤以外の全成分)の内、50質量部以上となるように含有させることが好ましく、60質量部以上がより好ましく、70質量部以上が特に好ましい。 The content of the polymerizable composition (B) may be an amount suitable for the purpose of use, but in order to prevent curing failure, it is included in the solid content (all components other than the solvent) in the polymerizable composition. , 50 parts by mass or more is preferable, 60 parts by mass or more is more preferable, and 70 parts by mass or more is particularly preferable.
<添加剤>
本発明の重合性組成物には、任意成分として、無機化合物、色材、潜在性エポキシ硬化剤、連鎖移動剤、増感剤、溶剤等の添加剤を用いることができる。<Additives>
In the polymerizable composition of the present invention, additives such as an inorganic compound, a coloring material, a latent epoxy curing agent, a chain transfer agent, a sensitizer, and a solvent can be used as optional components.
上記無機化合物としては、例えば、酸化ニッケル、酸化鉄、酸化イリジウム、酸化チタン、酸化亜鉛、酸化マグネシウム、酸化カルシウム、酸化カリウム、シリカ、アルミナ等の金属酸化物;層状粘土鉱物、ミロリブルー、炭酸カルシウム、炭酸マグネシウム、コバルト系、マンガン系、ガラス粉末(特にガラスフリット)、マイカ、タルク、カオリン、フェロシアン化物、各種金属硫酸塩、硫化物、セレン化物、アルミニウムシリケート、カルシウムシリケート、水酸化アルミニウム、白金、金、銀、銅等が挙げられる。これらの無機化合物は、例えば、充填剤、反射防止剤、導電材、安定剤、難燃剤、機械的強度向上剤、特殊波長吸収剤、発インク剤等として用いられる。 Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica and alumina; layered clay minerals, miloli blue and calcium carbonate. Magnesium carbonate, cobalt-based, manganese-based, glass powder (especially glass frit), mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfide, serene, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, Examples include gold, silver and copper. These inorganic compounds are used as, for example, fillers, antireflection agents, conductive materials, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink generators and the like.
上記色材としては、顔料、染料、天然色素等が挙げられる。これらの色材は、単独で又は2種以上を混合して用いることができる。 Examples of the coloring material include pigments, dyes, and natural pigments. These coloring materials can be used alone or in combination of two or more.
上記顔料としては、例えば、ニトロソ化合物;ニトロ化合物;アゾ化合物;ジアゾ化合物;キサンテン化合物;キノリン化合物;アントラキノン化合物;クマリン化合物;フタロシアニン化合物;イソインドリノン化合物;イソインドリン化合物;キナクリドン化合物;アンタンスロン化合物;ペリノン化合物;ペリレン化合物;ジケトピロロピロール化合物;チオインジゴ化合物;ジオキサジン化合物;トリフェニルメタン化合物;キノフタロン化合物;ナフタレンテトラカルボン酸;アゾ染料、シアニン染料の金属錯体化合物;レーキ顔料;ファーネス法、チャンネル法又はサーマル法によって得られるカーボンブラック、或いはアセチレンブラック、ケッチェンブラック又はランプブラック等のカーボンブラック;上記カーボンブラックをエポキシ樹脂で調整又は被覆したもの、上記カーボンブラックを予め溶媒中で樹脂で分散処理し、20〜200mg/gの樹脂を吸着させたもの、上記カーボンブラックを酸性又はアルカリ性表面処理したもの、平均粒径が8nm以上でDBP吸油量が90ml/100g以下のカーボンブラック、950℃における揮発分中のCO及びCO2から算出した全酸素量が、表面積100m2当たり9mg以上であるカーボンブラック;黒鉛、黒鉛化カーボンブラック、活性炭、炭素繊維、カーボンナノチューブ、カーボンマイクロコイル、カーボンナノホーン、カーボンエアロゲル、フラーレン;アニリンブラック、ピグメントブラック7、チタンブラック;酸化クロム緑、ミロリブルー、コバルト緑、コバルト青、マンガン系、フェロシアン化物、リン酸塩群青、紺青、ウルトラマリン、セルリアンブルー、ピリジアン、エメラルドグリーン、硫酸鉛、黄色鉛、亜鉛黄、べんがら(赤色酸化鉄(III))、カドミウム赤、合成鉄黒、アンバー等の有機又は無機顔料を用いることができる。これらの顔料は単独で、或いは複数を混合して用いることができる。Examples of the pigment include nitroso compounds; nitro compounds; azo compounds; diazo compounds; xanthene compounds; quinoline compounds; anthraquinone compounds; coumarin compounds; phthalocyanine compounds; isoindolinone compounds; isoindolin compounds; quinacridone compounds; antanthurone compounds; perinone. Compounds; perylene compounds; diketopyrrolopyrrole compounds; thioindigo compounds; dioxazine compounds; triphenylmethane compounds; quinophthalone compounds; naphthalenetetracarboxylic acids; azo dyes, cyanine dye metal complex compounds; lake pigments; furnace method, channel method or thermal Carbon black obtained by the method, or carbon black such as acetylene black, ketjen black, or lamp black; the above carbon black adjusted or coated with an epoxy resin, the above carbon black is previously dispersed with a resin in a solvent, and 20 A compound in which a resin of ~ 200 mg / g is adsorbed, a compound in which the above carbon black is subjected to an acidic or alkaline surface treatment, a carbon black having an average particle size of 8 nm or more and a DBP oil absorption of 90 ml / 100 g or less, in a volatile matter at 950 ° C. Carbon black in which the total amount of oxygen calculated from CO and CO 2 is 9 mg or more per 100 m 2 of the surface area; graphite, graphite carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; Aniline Black, Pigment Black 7, Titanium Black; Chromium Oxide Green, Milori Blue, Cobalt Green, Cobalt Blue, Manganese, Ferocyanide, Phosphate Ultramarine, Navy Blue, Ultramarine, Cerulean Blue, Pyridian, Emerald Green, Lead Sulfate, Organic or inorganic pigments such as yellow lead, zinc yellow, red iron oxide (III), cadmium red, synthetic iron black, and amber can be used. These pigments can be used alone or in combination of two or more.
上記顔料としては、市販の顔料を用いることもでき、例えば、ピグメントレッド1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;ピグメントオレンジ13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;ピグメントイエロー1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;ピグメントグリ−ン7、10、36;ピグメントブルー15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;ピグメントバイオレット1、19、23、27、29、30、32、37、40、50等が挙げられる。 As the above pigment, a commercially available pigment can also be used. For example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like can be mentioned.
上記染料としては、アゾ染料、アントラキノン染料、インジゴイド染料、トリアリールメタン染料、キサンテン染料、アリザリン染料、アクリジン染料スチルベン染料、チアゾール染料、ナフトール染料、キノリン染料、ニトロ染料、インダミン染料、オキサジン染料、フタロシアニン染料、シアニン染料等の染料等が挙げられ、これらは複数を混合して用いてもよい。 Examples of the above dyes include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acrydin dyes, stillben dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, and phthalocyanine dyes. , Dyes such as cyanine dyes, and the like, and a plurality of these may be mixed and used.
上記潜在性エポキシ硬化剤としては、例えば、ジシアンジアミド、変性ポリアミン、ヒドラジド類、4,4'−ジアミノジフェニルスルホン、三フッ化ホウ素アミン錯塩、イミダゾール類、グアナミン類、イミダゾール類、ウレア類及びメラミン等が挙げられる。 Examples of the latent epoxy curing agent include dicyandiamide, modified polyamines, hydrazides, 4,4'-diaminodiphenylsulfone, boron trifluoride amine complex salt, imidazoles, guanamines, imidazoles, ureas and melamines. Can be mentioned.
上記連鎖移動剤又は増感剤としては、一般的に硫黄原子含有化合物が用いられる。例えばチオグリコール酸、チオリンゴ酸、チオサリチル酸、2−メルカプトプロピオン酸、3−メルカプトプロピオン酸、3−メルカプト酪酸、N−(2−メルカプトプロピオニル)グリシン、2−メルカプトニコチン酸、3−[N−(2−メルカプトエチル)カルバモイル]プロピオン酸、3−[N−(2−メルカプトエチル)アミノ]プロピオン酸、N−(3−メルカプトプロピオニル)アラニン、2−メルカプトエタンスルホン酸、3−メルカプトプロパンスルホン酸、4−メルカプトブタンスルホン酸、ドデシル(4−メチルチオ)フェニルエーテル、2−メルカプトエタノール、3−メルカプト−1,2−プロパンジオール、1−メルカプト−2−プロパノール、3−メルカプト−2−ブタノール、メルカプトフェノール、2−メルカプトエチルアミン、2−メルカプトイミダゾール、2−メルカプトベンゾイミダゾール、2−メルカプト−3−ピリジノール、2−メルカプトベンゾチアゾール、メルカプト酢酸、トリメチロールプロパントリス(3−メルカプトプロピオネート)、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)等のメルカプト化合物、該メルカプト化合物を酸化して得られるジスルフィド化合物、ヨード酢酸、ヨードプロピオン酸、2−ヨードエタノール、2−ヨードエタンスルホン酸、3−ヨードプロパンスルホン酸等のヨード化アルキル化合物、トリメチロールプロパントリス(3−メルカプトイソブチレート)、ブタンジオールビス(3−メルカプトイソブチレート)、ヘキサンジチオール、デカンジチオール、1,4−ジメチルメルカプトベンゼン、ブタンジオールビスチオプロピオネート、ブタンジオールビスチオグリコレート、エチレングリコールビスチオグリコレート、トリメチロールプロパントリスチオグリコレート、ブタンジオールビスチオプロピオネート、トリメチロールプロパントリスチオプロピオネート、トリメチロールプロパントリスチオグリコレート、ペンタエリスリトールテトラキスチオプロピオネート、ペンタエリスリトールテトラキスチオグリコレート、トリスヒドロキシエチルトリスチオプロピオネート、ジエチルチオキサントン、ジイソプロピルチオキサントン、下記化合物No.C1、トリメルカプトプロピオン酸トリス(2−ヒドロキシエチル)イソシアヌレート等の脂肪族多官能チオール化合物、昭和電工社製カレンズMT BD1、PE1、NR1等が挙げられる。 As the chain transfer agent or sensitizer, a sulfur atom-containing compound is generally used. For example, thioglycolic acid, thioapple acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3-[N-( 2-Mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutansulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol , 2-Mercaptoethylamine, 2-Mercaptoimidazole, 2-Mercaptobenzoimidazole, 2-Mercapto-3-pyridinol, 2-Mercaptobenzothiazole, Mercaptoacetic acid, Trimethylolpropanthris (3-mercaptopropionate), Pentaerythritoltetrakis Mercapto compounds such as (3-mercaptopropionate), disulfide compounds obtained by oxidizing the mercapto compounds, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid. Alkyliodated compounds such as, trimethylolpropanetris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decandithiol, 1,4-dimethylmercaptobenzene, butanediol bisthio. Propionate, Butanediol Bisthioglycolate, Ethethylene Glycol Bisthioglycolate, Trimethylol Propanetristhioglycolate, Butanediol Bisthiopropionate, Trimethylol Propanetristhiopropionate, Trimethylol Propanetristhioglycolate , Pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, diethylthioxanthone, diisopropylthioxanthone, the following compound No. Examples thereof include aliphatic polyfunctional thiol compounds such as C1, tris (2-hydroxyethyl) trimercaptopropionate, isocyanurate, and Karenz MT BD1, PE1, NR1 manufactured by Showa Denko.
上記溶剤としては、通常、前記の各成分(重合開始剤(A)及び重合性化合物(B)等)を溶解又は分散しえる溶剤、例えば、メチルエチルケトン、メチルアミルケトン、ジエチルケトン、アセトン、メチルイソプロピルケトン、メチルイソブチルケトン、シクロヘキサノン、2−ヘプタノン等のケトン類;エチルエーテル、ジオキサン、テトラヒドロフラン、1,2−ジメトキシエタン、1,2−ジエトキシエタン、ジプロピレングリコールジメチルエーテル等のエーテル系溶剤;酢酸メチル、酢酸エチル、酢酸−n−プロピル、酢酸イソプロピル、酢酸n−ブチル、酢酸シクロヘキシル、乳酸エチル、コハク酸ジメチル、テキサノール等のエステル系溶剤;エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル等のセロソルブ系溶剤;メタノール、エタノール、イソ−又はn−プロパノール、イソ−又はn−ブタノール、アミルアルコール等のアルコール系溶剤;エチレングリコールモノメチルアセテート、エチレングリコールモノエチルアセテート、プロピレングリコール−1−モノメチルエーテル−2−アセテート、ジプロピレングリコールモノメチルエーテルアセテート、3−メトキシブチルアセテート、エトキシエチルプロピオネート等のエーテルエステル系溶剤;ベンゼン、トルエン、キシレン等のBTX系溶剤;ヘキサン、ヘプタン、オクタン、シクロヘキサン等の脂肪族炭化水素系溶剤;テレピン油、D−リモネン、ピネン等のテルペン系炭化水素油;ミネラルスピリット、スワゾール#310(コスモ松山石油(株))、ソルベッソ#100(エクソン化学(株))等のパラフィン系溶剤;四塩化炭素、クロロホルム、トリクロロエチレン、塩化メチレン、1,2−ジクロロエタン等のハロゲン化脂肪族炭化水素系溶剤;クロロベンゼン等のハロゲン化芳香族炭化水素系溶剤;カルビトール系溶剤;アニリン;トリエチルアミン;ピリジン;酢酸;アセトニトリル;二硫化炭素;N,N−ジメチルホルムアミド;N,N−ジメチルアセトアミド;N−メチルピロリドン;ジメチルスルホキシド;水等を用いることができ、これらの溶剤は1種で又は2種以上の混合溶剤として使用することができる。
これらの中でも、アルカリ現像性、パターニング性、製膜性、溶解性の点から、ケトン類又はエーテルエステル系溶剤、特に、プロピレングリコール−1−モノメチルエーテル−2−アセテート(以下、「PGMEA」ともいう。)又はシクロヘキサノンが好ましく用いられる。
本発明の重合性組成物において、溶剤の含有量は、特に制限されず、各成分が均一に分散又は溶解され、また本発明の重合性組成物が各用途に適した液状ないしペースト状を呈する量であればよいが、通常、本発明の重合性組成物中の固形分(溶剤以外の全成分)の量が10〜90質量%となる範囲で溶剤を含有させることが好ましい。The solvent is usually a solvent capable of dissolving or dispersing each of the above components (polymerization initiator (A), polymerizable compound (B), etc.), for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl. Ketones such as ketone, methylisobutylketone, cyclohexanone, 2-heptanone; ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate , Ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol and the like; Alcohol-based solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate, Ether ester solvents such as dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate and ethoxyethyl propionate; BTX solvents such as benzene, toluene and xylene; aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane Solvents: Terpen-based hydrocarbon oils such as terepine oil, D-lymonen, and pinen; mineral spirits, paraffin solvents such as Swazole # 310 (Cosmo Matsuyama Petroleum Co., Ltd.), Solbesso # 100 (Exxon Chemical Co., Ltd.); Halogenated aliphatic hydrocarbon solvents such as carbon chloride, chloroform, trichloroethylene, methylene chloride, 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents; aniline; triethylamine; pyridine; acetic acid. Acetonitrile; carbon disulfide; N, N-dimethylformamide; N, N-dimethylacetamide; N-methylpyrrolidone; dimethylsulfoxide; water and the like can be used, and these solvents may be used alone or in admixture of two or more. It can be used as a solvent.
Among these, ketones or ether ester-based solvents, particularly propylene glycol-1-monomethyl ether-2-acetate (hereinafter, also referred to as "PGMEA") from the viewpoint of alkali developability, patterning property, film forming property, and solubility. ) Or cyclohexanone is preferably used.
In the polymerizable composition of the present invention, the content of the solvent is not particularly limited, each component is uniformly dispersed or dissolved, and the polymerizable composition of the present invention exhibits a liquid or paste suitable for each application. Although it may be an amount, it is usually preferable to contain the solvent in a range in which the amount of the solid content (all components other than the solvent) in the polymerizable composition of the present invention is 10 to 90% by mass.
また、本発明の重合性組成物は、有機重合体を用いることによって、硬化物の特性を改善することもできる。該有機重合体としては、例えば、ポリスチレン、ポリメチルメタクリレート、メチルメタクリレート−エチルアクリレート共重合体、ポリ(メタ)アクリル酸、スチレン−(メタ)アクリル酸共重合体、(メタ)アクリル酸−メチルメタクリレート共重合体、エチレン−塩化ビニル共重合体、エチレン−ビニル共重合体、ポリ塩化ビニル樹脂、ABS樹脂、ナイロン6、ナイロン66、ナイロン12、ウレタン樹脂、ポリカーボネートポリビニルブチラール、セルロースエステル、ポリアクリルアミド、飽和ポリエステル、フェノール樹脂、フェノキシ樹脂等が挙げられる。
上記有機重合体を使用する場合、その使用量は、重合性化合物(B)100質量部に対して、好ましくは10〜500質量部である。In addition, the polymerizable composition of the present invention can also improve the characteristics of the cured product by using an organic polymer. Examples of the organic polymer include polystyrene, polymethylmethacrylate, methylmethacrylate-ethylacrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, and (meth) acrylic acid-methylmethacrylate. Copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Examples thereof include polyester, phenol resin, and phenoxy resin.
When the above organic polymer is used, the amount used is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the polymerizable compound (B).
本発明の重合性組成物には、更に、界面活性剤、シランカップリング剤、メラミン化合物等を併用することができる。 Further, a surfactant, a silane coupling agent, a melamine compound and the like can be used in combination with the polymerizable composition of the present invention.
上記界面活性剤としては、パーフルオロアルキルリン酸エステル、パーフルオロアルキルカルボン酸塩等のフッ素系界面活性剤;高級脂肪酸アルカリ塩、アルキルスルホン酸塩、アルキル硫酸塩等のアニオン系界面活性剤;高級アミンハロゲン酸塩、第四級アンモニウム塩等のカチオン系界面活性剤;ポリエチレングリコールアルキルエーテル、ポリエチレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、脂肪酸モノグリセリド等の非イオン界面活性剤;両性界面活性剤;シリコーン系界面活性剤等の界面活性剤を用いることができ、これらは組合せて用いてもよい。 Examples of the surfactant include fluorine-based surfactants such as perfluoroalkyl phosphate and perfluoroalkyl carboxylate; anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates and alkyl sulfates; higher grades. Cationic surfactants such as amine halides and quaternary ammonium salts; nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, fatty acid monoglycerides; amphoteric surfactants; silicone-based surfactants Surfactants such as activators can be used, and these may be used in combination.
上記シランカップリング剤としては、例えば信越化学社製シランカップリング剤を用いることができ、その中でも、KBE−9007、KBM−502、KBE−403等の、イソシアネート基、メタクリロイル基又はエポキシ基を有するシランカップリング剤が好適に用いられる。 As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used, and among them, it has an isocyanate group, a methacryloyl group, or an epoxy group such as KBE-9007, KBM-502, and KBE-403. Silane coupling agents are preferably used.
上記メラミン化合物としては、(ポリ)メチロールメラミン、(ポリ)メチロールグリコールウリル、(ポリ)メチロールベンゾグアナミン、(ポリ)メチロールウレア等の窒素化合物中の活性メチロール基(CH2OH基)の全部又は一部(少なくとも2つ)がアルキルエーテル化された化合物等を挙げることができる。
ここで、アルキルエーテルを構成するアルキル基としては、メチル基、エチル基又はブチル基が挙げられ、互いに同一であってもよいし、異なっていてもよい。また、アルキルエーテル化されていないメチロール基は、一分子内で自己縮合していてもよく、二分子間で縮合して、その結果オリゴマー成分が形成されていてもよい。
具体的には、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン、テトラメトキシメチルグリコールウリル、テトラブトキシメチルグリコールウリル等を用いることができる。
これらの中でも、溶剤への溶解性、重合性組成物から結晶析出しにくいという点から、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン等のアルキルエーテル化されたメラミンが好ましい。Examples of the melamine compound include all or a part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycol uryl, (poly) methylolbenzoguanamine, and (poly) methylol urea. Examples thereof include compounds in which (at least two) are alkyl etherified.
Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group and a butyl group, which may be the same or different from each other. Further, the methylol group which has not been alkyl etherized may be self-condensed within one molecule, or may be condensed between two molecules to form an oligomer component as a result.
Specifically, hexamethoxymethylmelamine, hexabutoxymethylmelamine, tetramethoxymethylglycoluryl, tetrabutoxymethylglycoluryl and the like can be used.
Among these, alkyl etherified melamines such as hexamethoxymethylmelamine and hexabutoxymethylmelamine are preferable from the viewpoint of solubility in a solvent and difficulty in crystal precipitation from the polymerizable composition.
本発明の重合性組成物において、重合開始剤(A)及び重合性化合物(B)以外の任意成分(但し、無機化合物、色材、及び溶剤は除く)の使用量は、その使用目的に応じて適宜選択され特に制限されないが、好ましくは、重合性化合物(B)100質量部に対して合計で50質量部以下とする。 In the polymerizable composition of the present invention, the amount of optional components (excluding inorganic compounds, coloring materials, and solvents) other than the polymerization initiator (A) and the polymerizable compound (B) depends on the purpose of use. It is appropriately selected and is not particularly limited, but is preferably 50 parts by mass or less in total with respect to 100 parts by mass of the polymerizable compound (B).
本発明の重合性組成物は、エネルギー線を照射して硬化物とすることができる。該硬化物は、用途に応じた適宜な形状として形成される。例えば膜状の硬化物を形成する場合には、本発明の重合性組成物は、スピンコーター、ロールコーター、バーコーター、ダイコーター、カーテンコーター、各種の印刷、浸漬等の公知の手段で、ソーダガラス、石英ガラス、半導体基板、金属、紙、プラスチック等の支持基体上に適用することができる。また、一旦フィルム等の支持基体上に施した後、他の支持基体上に転写することもでき、その適用方法に制限はない。 The polymerizable composition of the present invention can be made into a cured product by irradiating it with energy rays. The cured product is formed into an appropriate shape according to the application. For example, when forming a film-like cured product, the polymerizable composition of the present invention is a soda by a known means such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing, and immersion. It can be applied on supporting substrates such as glass, quartz glass, semiconductor substrates, metals, paper, and plastics. Further, once applied on a support substrate such as a film, it can be transferred onto another support substrate, and there is no limitation on the application method.
本発明の重合性組成物を硬化させる際に用いられるエネルギー線の光源としては、超高圧水銀ランプ、高圧水銀ランプ、中圧水銀ランプ、低圧水銀ランプ、水銀蒸気アーク灯、キセノンアーク灯、カーボンアーク灯、メタルハライドランプ、蛍光灯、タングステンランプ、エキシマーランプ、殺菌灯、発光ダイオード、CRT光源等から得られる2000オングストローム〜7000オングストロームの波長を有する電磁波エネルギーや電子線、X線、放射線等の高エネルギー線を利用することができるが、好ましくは、波長300〜450nmの光を発光する超高圧水銀ランプ、水銀蒸気アーク灯、カーボンアーク灯、キセノンアーク灯等が用いられる。 As the light source of the energy ray used for curing the polymerizable composition of the present invention, an ultra-high pressure mercury lamp, a high pressure mercury lamp, a medium pressure mercury lamp, a low pressure mercury lamp, a mercury steam arc lamp, a xenon arc lamp, and a carbon arc High-energy rays such as electromagnetic energy, electron beam, X-ray, radiation, etc. having a wavelength of 2000 angstrom to 7000 angstrom obtained from lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, sterilization lamps, light emitting diodes, CRT light sources, etc. However, preferably, an ultra-high pressure mercury lamp, a mercury steam arc lamp, a carbon arc lamp, a xenon arc lamp, or the like that emits light having a wavelength of 300 to 450 nm is used.
更に、露光光源にレーザー光を用いることにより、マスクを用いずに、コンピューター等のデジタル情報から直接画像を形成するレーザー直接描画法が、生産性のみならず、解像性や位置精度等の向上も図れることから有用であり、そのレーザー光としては、340〜430nmの波長の光が好適に使用されるが、エキシマーレーザー、窒素レーザー、アルゴンイオンレーザー、ヘリウムカドミウムレーザー、ヘリウムネオンレーザー、クリプトンイオンレーザー、各種半導体レーザー及びYAGレーザー等の可視から赤外領域の光を発するものも用いることができる。これらのレーザー光を使用する場合には、好ましくは、可視から赤外の当該領域を吸収する増感色素が加えられる。 Furthermore, by using laser light as the exposure light source, the laser direct drawing method, which forms an image directly from digital information of a computer or the like without using a mask, improves not only productivity but also resolution and position accuracy. As the laser light, light having a wavelength of 340 to 430 nm is preferably used, but an excimer laser, a nitrogen laser, an argon ion laser, a helium cadmium laser, a helium neon laser, and a krypton ion laser are used. , Various semiconductor lasers, YAG lasers and the like that emit light in the visible to infrared region can also be used. When these laser beams are used, a sensitizing dye that absorbs the visible to infrared region is preferably added.
また、本発明の重合性組成物の硬化には、上記エネルギー線の照射後、加熱することが通常必要であり、40〜150℃程度の加熱が硬化率の点で好ましい。 Further, in order to cure the polymerizable composition of the present invention, it is usually necessary to heat after irradiation with the above energy rays, and heating at about 40 to 150 ° C. is preferable in terms of the curing rate.
本発明の重合性組成物は、光硬化性塗料又はワニス;光硬化性接着剤;金属用コーティング剤;プリント基板;カラーテレビ、PCモニタ、携帯情報端末、デジタルカメラ等のカラー表示の液晶表示素子におけるカラーフィルタ;CCDイメージセンサのカラーフィルタ;プラズマ表示パネル用の電極材料;粉末コーティング;印刷インク;印刷版;接着剤;歯科用組成物;ゲルコート;電子工学用のフォトレジスト;電気メッキレジスト;エッチングレジスト;ドライフィルム;はんだレジスト;種々の表示用途用のカラーフィルタを製造するための或いはプラズマ表示パネル、電気発光表示装置、及びLCDの製造工程においてそれらの構造を形成するためのレジスト;電気及び電子部品を封入するための組成物;ソルダーレジスト;磁気記録材料;微小機械部品;導波路;光スイッチ;メッキ用マスク;エッチングマスク;カラー試験系;ガラス繊維ケーブルコーティング;スクリーン印刷用ステンシル;ステレオリトグラフィによって三次元物体を製造するための材料;ホログラフィ記録用材料;画像記録材料;微細電子回路;脱色材料;画像記録材料のための脱色材料;マイクロカプセルを使用する画像記録材料用の脱色材料;印刷配線板用フォトレジスト材料;UV及び可視レーザー直接画像系用のフォトレジスト材料;プリント回路基板の逐次積層における誘電体層形成に使用するフォトレジスト材料又は保護膜等の各種の用途に使用することができ、その用途に特に制限はない。 The polymerizable composition of the present invention is a photocurable paint or varnish; a photoresist adhesive; a coating agent for metals; a printed substrate; a color display liquid crystal display element for a color television, a PC monitor, a mobile information terminal, a digital camera, or the like. Color filters in; CCD image sensor color filters; Electrode materials for plasma display panels; Powder coatings; Printing inks; Printing plates; Adhesives; Dental compositions; Gel coats; Photoresists for electronic engineering; Electroplated resists; Etching Resists; Dry Films; Solder Resists; Resists for Manufacturing Color Filters for Various Display Applications or for Forming Their Structures in Plasma Display Panels, Electroluminescent Display, and LCD Manufacturing Processes; Electrical and Electronic Compositions for encapsulating parts; solder resists; magnetic recording materials; micromechanical parts; waveguides; optical switches; plating masks; etching masks; color test systems; glass fiber cable coatings; screen printing stencil; stereolithography Materials for manufacturing three-dimensional objects by; holography recording materials; image recording materials; microelectronic circuits; decolorizing materials; decolorizing materials for image recording materials; decolorizing materials for image recording materials using microcapsules; printing Photoresist material for wiring board; photoresist material for UV and visible laser direct imaging system; photoresist material or protective film used for forming a dielectric layer in sequential lamination of printed circuit boards. It can be used, and there are no particular restrictions on its use.
本発明の重合性組成物は、液晶表示パネル用スペーサーを形成する目的及び垂直配向型液晶表示素子用突起を形成する目的で使用することもできる。特に垂直配向型液晶表示素子用の突起とスペーサーを同時に形成するための感光性樹脂組成物として有用である。 The polymerizable composition of the present invention can also be used for the purpose of forming a spacer for a liquid crystal display panel and for forming a protrusion for a vertically oriented liquid crystal display element. In particular, it is useful as a photosensitive resin composition for simultaneously forming protrusions and spacers for a vertically oriented liquid crystal display element.
上記の液晶表示パネル用スペーサーは、(I)本発明の重合性組成物の塗膜を基板上に形成する工程、(2)該塗膜に所定のパターン形状を有するマスクを介してエネルギー線(光)を照射する工程、(3)露光後のベーク工程、(4)露光後の被膜を現像する工程、(5)現像後の該被膜を加熱する工程により好ましく形成される。 The above spacer for a liquid crystal display panel includes (I) a step of forming a coating film of the polymerizable composition of the present invention on a substrate, and (2) energy rays (2) through a mask having a predetermined pattern shape on the coating film. It is preferably formed by a step of irradiating (light), (3) a baking step after exposure, (4) a step of developing a film after exposure, and (5) a step of heating the film after development.
色材を添加した本発明の重合性組成物は、カラーフィルタにおけるRGB等の各画素を構成するレジストや、各画素の隔壁を形成するブラックマトリクス用レジストとして好適に用いられる。更に、撥インク剤を添加するブラックマトリクス用レジストの場合、プロファイル角が50°以上であるインクジェット方式カラーフィルタ用隔壁に好ましく用いられる。該撥インク剤としては、フッ素系界面活性剤及びフッ素系界面活性剤を含有する組成物が好適に用いられる。 The polymerizable composition of the present invention to which a coloring material is added is suitably used as a resist that constitutes each pixel such as RGB in a color filter, and a resist for a black matrix that forms a partition wall of each pixel. Further, in the case of a black matrix resist to which an ink repellent is added, it is preferably used for an inkjet color filter partition wall having a profile angle of 50 ° or more. As the ink repellent, a composition containing a fluorine-based surfactant and a fluorine-based surfactant is preferably used.
上記インクジェット方式カラーフィルタ用隔壁に用いた場合、本発明の重合性組成物から形成された隔壁が被転写体上を区画し、区画された被転写体上の凹部にインクジェット法により液滴を付与して画像領域を形成する方法により光学素子が製造される。この際、上記液滴が着色剤を含有し、上記画像領域が着色されていることが好ましく、その場合には、上記の製造方法により作製された光学素子は、基板上に複数の着色領域からなる画素群と該画素群の各着色領域を離隔する隔壁を少なくとも有するものとなる。 When used for the partition wall for an inkjet color filter, the partition wall formed from the polymerizable composition of the present invention partitions on the transferred body, and droplets are applied to the recesses on the partitioned partition by the inkjet method. The optical element is manufactured by the method of forming an image region. At this time, it is preferable that the droplets contain a colorant and the image region is colored. In that case, the optical element manufactured by the above manufacturing method is formed from a plurality of colored regions on the substrate. It has at least a partition wall that separates the pixel group and each colored region of the pixel group.
本発明の重合性組成物は、保護膜又は絶縁膜用組成物としても用いることができる。この場合、紫外線吸収剤、アルキル化変性メラミン及び/又はアクリル変性メラミン、分子中にアルコール性水酸基を含有する1又は2官能の(メタ)アクリレートモノマー及び/又はシリカゾルを含有することができる。 The polymerizable composition of the present invention can also be used as a composition for a protective film or an insulating film. In this case, an ultraviolet absorber, an alkylation-modified melamine and / or an acrylic-modified melamine, a mono- or bifunctional (meth) acrylate monomer and / or a silica sol containing an alcoholic hydroxyl group in the molecule can be contained.
上記絶縁膜は、剥離可能な支持基材上に絶縁樹脂層が設けられた積層体における該絶縁樹脂層に用いられ、該積層体は、アルカリ水溶液による現像が可能なものであり、絶縁樹脂層の膜厚が10〜100μmであることが好ましい。 The insulating film is used for the insulating resin layer in a laminated body in which an insulating resin layer is provided on a peelable supporting base material, and the laminated body can be developed with an alkaline aqueous solution and is an insulating resin layer. The thickness of the film is preferably 10 to 100 μm.
本発明の重合性組成物は、無機化合物を含有させることで、感光性ペースト組成物として用いることができる。該感光性ペースト組成物は、プラズマディスプレイパネルの隔壁パターン、誘電体パターン、電極パターン及びブラックマトリックスパターン等の焼成物パターンを形成するために用いることができる。 The polymerizable composition of the present invention can be used as a photosensitive paste composition by containing an inorganic compound. The photosensitive paste composition can be used to form a fired product pattern such as a partition wall pattern, a dielectric pattern, an electrode pattern and a black matrix pattern of a plasma display panel.
以下、実施例及び比較例を挙げて本発明を更に詳細に説明するが、本発明はこれらの実施例等に限定されるものではない。なお、以下で得られた化合物の性状は、大気圧下、25℃におけるものである。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples and the like. The properties of the compound obtained below are those at 25 ° C. under atmospheric pressure.
〔製造例1〕オキシム化合物1の合成
100mL四つ口フラスコに塩化アルミニウム2.40gと、ジクロロエタン(EDC)34.56gを入れ氷浴上−5℃で攪拌した。そこに9,9’−ジヘキシルフルオレン5.02g及びオクタノイルクロリド2.44gをジクロロエタン20g中に溶解させた溶液を滴下して加えた。室温まで昇温後3時間攪拌し、再び氷浴で冷却し、5質量%水酸化ナトリウム水溶液を20g滴下した。油水分離を行い、有機層を水で3回水洗した。有機層をエバポレータで減圧濃縮し、下記のケトン化合物1を収量6.91gで得た。[Production Example 1] Synthesis of Oxime Compound 1 2.40 g of aluminum chloride and 34.56 g of dichloroethane (EDC) were placed in a 100 mL four-necked flask and stirred on an ice bath at −5 ° C. A solution prepared by dissolving 5.02 g of 9,9'-dihexylfluorene and 2.44 g of octanoyl chloride in 20 g of dichloroethane was added dropwise thereto. After raising the temperature to room temperature, the mixture was stirred for 3 hours, cooled again in an ice bath, and 20 g of a 5 mass% sodium hydroxide aqueous solution was added dropwise. Oil-water separation was performed, and the organic layer was washed with water three times. The organic layer was concentrated under reduced pressure with an evaporator to obtain the following ketone compound 1 in a yield of 6.91 g.
100mL四つ口フラスコにケトン化合物1を3.00g、塩酸ヒドロキシルアミン0.50g、ジメチルホルムアミド(DMF)9.30g、ピリジン0.62gの順で加えオイルバス上80℃で5時間加熱攪拌した。室温まで冷却後イオン水50gにあけた。酢酸エチルを加え油水分離を行い、有機層を水で3回水洗した。有機層をエバポレータで減圧濃縮し、下記のオキシム化合物1を収量3.10gで得た。 To a 100 mL four-necked flask, 3.00 g of ketone compound 1, 0.50 g of hydroxylamine hydrochloride, 9.30 g of dimethylformamide (DMF), and 0.62 g of pyridine were added in this order, and the mixture was heated and stirred on an oil bath at 80 ° C. for 5 hours. After cooling to room temperature, it was opened in 50 g of ionized water. Ethyl acetate was added, oil-water separation was performed, and the organic layer was washed with water three times. The organic layer was concentrated under reduced pressure with an evaporator to obtain the following oxime compound 1 in a yield of 3.10 g.
〔製造例2〕オキシム化合物2の合成
100mL四つ口フラスコにケトン化合物1を2.00g、DMF6.39g、35質量%塩酸0.45gの順で加え、氷浴上5℃で攪拌を行った。そこに亜硝酸イソブチル0.50gを滴下して加えた。室温まで昇温後、6時間攪拌した。その後イオン水50gにあけた。酢酸エチルを加え油水分離を行い、有機層を水で3回水洗した。有機層をエバポレータで減圧濃縮し、下記のオキシム化合物2を収量2.13gで得た。[Production Example 2] Synthesis of Oxime Compound 2 2.00 g of ketone compound 1, 6.39 g of DMF, and 0.45 g of 35% by mass hydrochloric acid were added in this order to a 100 mL four-necked flask, and the mixture was stirred on an ice bath at 5 ° C. .. 0.50 g of isobutyl nitrite was added dropwise thereto. After raising the temperature to room temperature, the mixture was stirred for 6 hours. Then, it was opened in 50 g of ionized water. Ethyl acetate was added, oil-water separation was performed, and the organic layer was washed with water three times. The organic layer was concentrated under reduced pressure with an evaporator to obtain the following oxime compound 2 in a yield of 2.13 g.
〔製造例3〕オキシム化合物3の合成
100mL四つ口フラスコに下記ケトン化合物2を3.63g、塩酸ヒドロキシルアミン1.67g、DMF11.78g、ピリジン1.90gの順で加えオイルバス上80℃で5時間加熱攪拌した。室温まで冷却後イオン水50gにあけた。酢酸エチルを加え油水分離を行い、有機層を水で3回水洗した。有機層をエバポレータで減圧濃縮した。残渣にメタノールを加え晶析を行い、下記オキシム化合物3を収量3.13gで得た。[Production Example 3] Synthesis of Oxime Compound 3 Add the following ketone compound 2 to a 100 mL four-necked flask in the order of 3.63 g, hydroxylamine hydrochloride 1.67 g, DMF 11.78 g, and pyridine 1.90 g at 80 ° C. on an oil bath. The mixture was heated and stirred for 5 hours. After cooling to room temperature, it was opened in 50 g of ionized water. Ethyl acetate was added, oil-water separation was performed, and the organic layer was washed with water three times. The organic layer was concentrated under reduced pressure with an evaporator. Methanol was added to the residue and crystallization was carried out to obtain the following oxime compound 3 in a yield of 3.13 g.
〔製造例4〕オキシム化合物4の合成
100ml四つ口フラスコに、1−(9,9−ジメチル−7−(2−メチルベンゾイル)−9H−フルオレン−2−イル)オクタン−1−オン1.0eq.を加え、ジメチルホルムアミド(理論収量の400重量%)に溶解した。溶液にヒドロキシアンモニウムクロリド1.2eq.及びピリジン1.2eq.を加えた。反応混合物を55℃で9時間加熱攪拌し、イオン交換水を加え、酢酸エチルで抽出した。有機層を5質量%塩酸、イオン交換水、飽和炭酸水素ナトリウム水溶液で2回、イオン交換水で3回、という順で洗浄し、硫酸マグネシウムにより乾燥させ、濃縮した。残渣をシリカゲルカラムクロマトグラフィー(溶離剤=酢酸エチル:ヘキサン=1:6)により精製し、オキシム化合物4を収率70%で得た。[Production Example 4] Synthesis of Oxime Compound 4 In a 100 ml four-necked flask, 1- (9,9-dimethyl-7- (2-methylbenzoyl) -9H-fluorene-2-yl) octane-1-one. 0eq. Was added and dissolved in dimethylformamide (400% by weight of theoretical yield). Hydroxyammonium chloride 1.2 eq in solution. And pyridine 1.2 eq. Was added. The reaction mixture was heated and stirred at 55 ° C. for 9 hours, ion-exchanged water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with 5% by mass hydrochloric acid, ion-exchanged water and saturated aqueous sodium hydrogen carbonate solution, and three times with ion-exchanged water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent = ethyl acetate: hexane = 1: 6) to obtain oxime compound 4 in a yield of 70%.
〔製造例4〕オキシム化合物5の合成
100ml四つ口フラスコに、3−シクロペンチル−1−(9,9−ジメチル―7−ニトロ−9H−フルオレン−2−イル)プロパン−1−オン1.0eq.を加え、ジメチルホルムアミド(理論収量の400重量%)に溶解した。溶液にヒドロキシアンモニウムクロリド1.2eq.及びピリジン1.2eq.を加えた。反応混合物を55℃で7時間加熱攪拌し、イオン交換水を加え、酢酸エチルで抽出した。有機層をイオン交換水で3回洗浄し、硫酸マグネシウムにより乾燥させ、濃縮した。これにメタノール(理論収量の1700重量%)を加え晶析を行い、オキシム化合物5を淡褐色粉状化合物として収率65%で得た。[Production Example 4] Synthesis of Oxime Compound 5 In a 100 ml four-necked flask, 3-cyclopentyl-1- (9,9-dimethyl-7-nitro-9H-fluorene-2-yl) propan-1-one 1.0eq .. Was added and dissolved in dimethylformamide (400% by weight of theoretical yield). Hydroxyammonium chloride 1.2 eq in solution. And pyridine 1.2 eq. Was added. The reaction mixture was heated and stirred at 55 ° C. for 7 hours, ion-exchanged water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed 3 times with ion-exchanged water, dried over magnesium sulfate and concentrated. Methanol (1700% by weight of the theoretical yield) was added thereto and crystallization was carried out to obtain oxime compound 5 as a light brown powdery compound in a yield of 65%.
〔実施例1−1〕化合物No.1の合成
100mL四つ口フラスコにオキシム化合物1を1.00gと、アセトニトリル6.00gを入れ室温で攪拌した。そこに1,1’−カルボニルジイミダゾール0.41gをアセトニトリル5g中に分散させた溶液を10分かけて加えた。3時間攪拌後、析出した結晶を除き、ろ液を濃縮した。更に3時間減圧乾燥を行い、白色粉状化合物を収率59%で得た。得られた固体のTG−DTA(融点/℃)、1H−NMRを分析し、目的物である化合物No.1であることを確認した。分析結果を〔表1〕及び〔表2〕に示す。[Example 1-1] Compound No. Synthesis of No. 1 1.00 g of oxime compound 1 and 6.00 g of acetonitrile were placed in a 100 mL four-necked flask and stirred at room temperature. A solution in which 0.41 g of 1,1'-carbonyldiimidazole was dispersed in 5 g of acetonitrile was added thereto over 10 minutes. After stirring for 3 hours, the precipitated crystals were removed and the filtrate was concentrated. Further, it was dried under reduced pressure for 3 hours to obtain a white powdery compound in a yield of 59%. The obtained solid TG-DTA (melting point / ° C.) and 1 1 H-NMR were analyzed, and the target compound No. It was confirmed that it was 1. The analysis results are shown in [Table 1] and [Table 2].
〔実施例1−2〕化合物No.2の合成
100mL四つ口フラスコにオキシム化合物2を2.13gと、アセトニトリル29.00gを入れ室温で攪拌した。そこに1,1’−カルボニルジイミダゾール0.86gをアセトニトリル5g中に分散させた溶液を10分かけて加えた。1時間攪拌後、析出した結晶を除き、ろ液を濃縮した。更に4時間減圧乾燥を行い、白色粉状化合物を収率51%で得た。得られた固体のTG−DTA(融点/℃)、1H−NMRを分析し、目的物である化合物No.2であることを確認した。分析結果を〔表1〕及び〔表2〕に示す。[Example 1-2] Compound No. Synthesis of 2 2.13 g of oxime compound 2 and 29.00 g of acetonitrile were placed in a 100 mL four-necked flask and stirred at room temperature. A solution in which 0.86 g of 1,1'-carbonyldiimidazole was dispersed in 5 g of acetonitrile was added thereto over 10 minutes. After stirring for 1 hour, the precipitated crystals were removed and the filtrate was concentrated. Further, it was dried under reduced pressure for 4 hours to obtain a white powdery compound in a yield of 51%. The obtained solid TG-DTA (melting point / ° C.) and 1 1 H-NMR were analyzed, and the target compound No. It was confirmed that it was 2. The analysis results are shown in [Table 1] and [Table 2].
〔実施例1−3〕化合物No.3の合成
100mL四つ口フラスコに、オキシム化合物3を1.18g、1,1’−カルボニルジイミダゾール1.17g及びテトラヒドロフラン(THF)1.04gを入れ室温で2時間攪拌した。そこにピペリジン0.61gを滴下して加え、オイルバス上60℃で6時間攪拌した。室温まで冷却後、エバポレータで減圧溶媒留去し、残渣にクロロホルムを加え、イオン交換水で5回水洗を行った。有機層を減圧濃縮し、メタノールを加えて晶析を行い、薄黄色粉状物を収率74%で得た。得られた固体のTG−DTA(融点/℃)、1H−NMRを分析し、目的物である化合物No.3であることを確認した。分析結果を〔表1〕及び〔表2〕に示す。[Example 1-3] Compound No. Synthesis of 3 In a 100 mL four-necked flask, 1.18 g of oxime compound 3, 1.17 g of 1,1'-carbonyldiimidazole and 1.04 g of tetrahydrofuran (THF) were placed and stirred at room temperature for 2 hours. 0.61 g of piperidine was added dropwise thereto, and the mixture was stirred on an oil bath at 60 ° C. for 6 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure with an evaporator, chloroform was added to the residue, and the residue was washed with ion-exchanged water 5 times. The organic layer was concentrated under reduced pressure, methanol was added, and crystallization was performed to obtain a pale yellow powder in a yield of 74%. The obtained solid TG-DTA (melting point / ° C.) and 1 1 H-NMR were analyzed, and the target compound No. It was confirmed that it was 3. The analysis results are shown in [Table 1] and [Table 2].
〔実施例1−4〕化合物No.50の合成
100ml四つ口フラスコに、オキシム化合物4を1.0eq.、ジクロロエタン(理論収量の600重量%)、トリエチルアミン2.0eq.を加え、氷浴上5℃で攪拌を行った。そこにクロロギ酸4−ニトロフェニル1.5eq.をジクロロエタンに溶かしたものを滴下して加えた。滴下終了後、室温で1時間攪拌した。再び氷浴上5℃まで冷却後、アニリン1.5eq.を滴下して加えた。室温で1時間攪拌し、減圧溶媒留去した。そこに酢酸エチルとイオン交換水を加え、油水分離を行った。更に有機層を1質量%水酸化ナトリウム水溶液で2回、イオン交換水で2回洗浄し、硫酸マグネシウムにより乾燥させ、濃縮した。残渣をシリカゲルカラムクロマトグラフィー(溶離剤=酢酸エチル:トルエン=1:30)により精製し、化合物No.50を淡黄色透明固体として収率56%で得た。得られた化合物のTG−DTA(融点)、1H−NMRを分析した。結果を〔表2A〕及び〔表2B〕に示す。化合物No.50の合成の反応式は下記のとおりである。[Example 1-4] Compound No. Synthesis of 50 In a 100 ml four-necked flask, oxime compound 4 was added to 1.0 eq. , Dichloroethane (600% by weight of theoretical yield), triethylamine 2.0eq. Was added, and the mixture was stirred on an ice bath at 5 ° C. There, 4-nitrophenyl chloroformate 1.5 eq. Was dissolved in dichloroethane and added dropwise. After completion of the dropping, the mixture was stirred at room temperature for 1 hour. After cooling to 5 ° C. on an ice bath again, aniline 1.5 eq. Was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. Ethyl acetate and ion-exchanged water were added thereto, and oil-water separation was performed. Further, the organic layer was washed twice with a 1% by mass aqueous sodium hydroxide solution and twice with ion-exchanged water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent = ethyl acetate: toluene = 1:30) to obtain Compound No. 50 was obtained as a pale yellow transparent solid in a yield of 56%. The TG-DTA (melting point) and 1 1 H-NMR of the obtained compound were analyzed. The results are shown in [Table 2A] and [Table 2B]. Compound No. The reaction formula of the synthesis of 50 is as follows.
〔実施例1−5〕化合物No.51の合成
100ml四つ口フラスコに、オキシム化合物4を1.0eq.、ジクロロエタン(理論収量の600重量%)、トリエチルアミン2.0eq.を加え、氷浴上5℃で攪拌を行った。そこにクロロギ酸4−ニトロフェニル1.5eq.をジクロロエタンに溶かしたものを滴下して加えた。滴下終了後、室温で1時間攪拌した。再び氷浴上5℃まで冷却後、ピペリジン1.5eq.を滴下して加えた。室温で1時間攪拌し、減圧溶媒留去した。そこに酢酸エチルとイオン交換水を加え、油水分離を行った。更に有機層を1質量%水酸化ナトリウム水溶液で2回、イオン交換水で3回洗浄し、硫酸マグネシウムにより乾燥させ、濃縮した。残渣をシリカゲルカラムクロマトグラフィー(溶離剤=酢酸エチル:トルエン=1:10)により精製し、化合物No.51を淡黄色透明液体として収率67%で得た。得られた化合物のTG−DTA(融点)、1H−NMRを分析した。結果を〔表2B〕に示す。化合物No.51の合成の反応式は下記のとおりである。[Example 1-5] Compound No. Synthesis of 51 In a 100 ml four-necked flask, oxime compound 4 was added to 1.0 eq. , Dichloroethane (600% by weight of theoretical yield), triethylamine 2.0eq. Was added, and the mixture was stirred on an ice bath at 5 ° C. There, 4-nitrophenyl chloroformate 1.5 eq. Was dissolved in dichloroethane and added dropwise. After completion of the dropping, the mixture was stirred at room temperature for 1 hour. After cooling to 5 ° C. on an ice bath again, piperidine 1.5 eq. Was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. Ethyl acetate and ion-exchanged water were added thereto, and oil-water separation was performed. Further, the organic layer was washed twice with a 1% by mass aqueous sodium hydroxide solution and three times with ion-exchanged water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent = ethyl acetate: toluene = 1:10) to obtain Compound No. 51 was obtained as a pale yellow transparent liquid in a yield of 67%. The TG-DTA (melting point) and 1 1 H-NMR of the obtained compound were analyzed. The results are shown in [Table 2B]. Compound No. The reaction formula for the synthesis of 51 is as follows.
〔実施例1−6〕化合物No.52の合成
100ml四つ口フラスコに、オキシム化合物5を1.0eq.、ジクロロエタン(理論収量の600重量%)、トリエチルアミン2.0eq.を加え、氷浴上5℃で攪拌を行った。そこにクロロギ酸4−ニトロフェニル1.5eq.をジクロロエタンに溶かしたものを滴下して加えた。滴下終了後、室温で1時間攪拌した。再び氷浴上5℃まで冷却後、ジブチルアミン1.5eq.を滴下して加えた。室温で1時間攪拌し、減圧溶媒留去した。そこに酢酸エチルとイオン交換水を加え、油水分離を行った。更に有機層を1質量%水酸化ナトリウム水溶液で2回、イオン交換水で3回洗浄し、硫酸マグネシウムにより乾燥させ、濃縮した。これにメタノール(理論収量の600重量%)を加え晶析を行い、化合物No.52を淡茶色固体として収率78%で得た。得られた化合物のTG−DTA(融点)、1H−NMRを分析した。結果を〔表2A〕及び〔表2B〕に示す。化合物No.52の合成の反応式は下記のとおりである。[Example 1-6] Compound No. Synthesis of 52 In a 100 ml four-necked flask, oxime compound 5 was added to 1.0 eq. , Dichloroethane (600% by weight of theoretical yield), triethylamine 2.0eq. Was added, and the mixture was stirred on an ice bath at 5 ° C. There, 4-nitrophenyl chloroformate 1.5 eq. Was dissolved in dichloroethane and added dropwise. After completion of the dropping, the mixture was stirred at room temperature for 1 hour. After cooling to 5 ° C. on an ice bath again, dibutylamine 1.5 eq. Was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. Ethyl acetate and ion-exchanged water were added thereto, and oil-water separation was performed. Further, the organic layer was washed twice with a 1% by mass aqueous sodium hydroxide solution and three times with ion-exchanged water, dried over magnesium sulfate, and concentrated. Methanol (600% by weight of the theoretical yield) was added thereto for crystallization, and the compound No. 52 was obtained as a light brown solid in a yield of 78%. The TG-DTA (melting point) and 1 1 H-NMR of the obtained compound were analyzed. The results are shown in [Table 2A] and [Table 2B]. Compound No. The reaction formula for the synthesis of 52 is as follows.
〔実施例1−7〕化合物No.53の合成
100ml四つ口フラスコに、オキシム化合物5を1.0eq.、ジクロロエタン(理論収量の600重量%)、トリエチルアミン2.0eq.を加え、氷浴上5℃で攪拌を行った。そこにクロロギ酸4−ニトロフェニル1.5eq.をジクロロエタンに溶かしたものを滴下して加えた。滴下終了後、室温で1時間攪拌した。再び氷浴上5℃まで冷却後、3,5−ジメチルピペリジン1.5eq.を滴下して加えた。室温で1時間攪拌し、減圧溶媒留去した。そこに酢酸エチルとイオン交換水を加え、油水分離を行った。更に有機層を、イオン交換水で3回洗浄し、硫酸マグネシウムにより乾燥させ、濃縮した。これにエタノール(理論収量の7000重量%)を加え晶析を行い、化合物No.53を淡黄色固体として収率79%で得た。得られた化合物のTG−DTA(融点)、1H−NMRを分析した。結果を〔表2A〕及び〔表2B〕に示す。化合物No.53の合成の反応式は下記のとおりである。[Example 1-7] Compound No. Synthesis of 53 In a 100 ml four-necked flask, oxime compound 5 was added to 1.0 eq. , Dichloroethane (600% by weight of theoretical yield), triethylamine 2.0eq. Was added, and the mixture was stirred on an ice bath at 5 ° C. There, 4-nitrophenyl chloroformate 1.5 eq. Was dissolved in dichloroethane and added dropwise. After completion of the dropping, the mixture was stirred at room temperature for 1 hour. After cooling to 5 ° C. on an ice bath again, 3,5-dimethylpiperidine 1.5 eq. Was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. Ethyl acetate and ion-exchanged water were added thereto, and oil-water separation was performed. Further, the organic layer was washed with ion-exchanged water three times, dried over magnesium sulfate, and concentrated. Ethanol (7000% by weight of the theoretical yield) was added thereto for crystallization, and the compound No. 53 was obtained as a pale yellow solid in a yield of 79%. The TG-DTA (melting point) and 1 1 H-NMR of the obtained compound were analyzed. The results are shown in [Table 2A] and [Table 2B]. Compound No. The reaction formula for the synthesis of 53 is as follows.
〔実施例1−8〕化合物No.54の合成
100ml四つ口フラスコに、オキシム化合物4を1.0eq.、アセトニトリル(理論収量の200重量%)を加え、室温で攪拌を行った。そこに1,1’−カルボニルジイミダゾールを1.1eq.加え、室温で30分間攪拌し、減圧溶媒留去した。シリカゲルカラムクロマトグラフィー(溶離剤=酢酸エチル:ヘキサン=60:40)により精製し、化合物No.54を淡黄色固体として収率44%で得た。得られた化合物のTG−DTA(融点)、1H−NMRを分析した。結果を〔表2A〕及び〔表2B〕に示す。化合物No.54の合成の反応式は下記のとおりである。[Example 1-8] Compound No. Synthesis of 54 In a 100 ml four-necked flask, oxime compound 4 was added to 1.0 eq. , Acetonitrile (200% by weight of the theoretical yield) was added, and the mixture was stirred at room temperature. There, 1,1'-carbonyldiimidazole was added 1.1 eq. In addition, the mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. Purified by silica gel column chromatography (eluent = ethyl acetate: hexane = 60: 40), compound No. 54 was obtained as a pale yellow solid in a yield of 44%. The TG-DTA (melting point) and 1 1 H-NMR of the obtained compound were analyzed. The results are shown in [Table 2A] and [Table 2B]. Compound No. The reaction formula for the synthesis of 54 is as follows.
〔比較例1−1〕
比較化合物No.1として、下記化合物を用いた。
Comparative Compound No. As 1, the following compound was used.
〔評価1〕溶剤溶解性試験
上記化合物No.1〜No.3及び比較化合物No.1を1.0g測り取り、そこに室温(25℃)で下記〔表3〕に示す各溶剤を加え、完全に溶解したときの溶剤の添加量を測定し、化合物の溶解性を下記計算式により算出した。結果を[表3]に示す。
化合物の各溶剤への溶解性(%)=1.0g/(1.0g+溶剤の添加量g)×100[Evaluation 1] Solvent solubility test The above compound No. 1-No. 3 and Comparative Compound No. Weigh 1.0 g of 1 and add each solvent shown in the following [Table 3] to it at room temperature (25 ° C), measure the amount of solvent added when it is completely dissolved, and calculate the solubility of the compound by the following formula. Calculated by The results are shown in [Table 3].
Solubility of compound in each solvent (%) = 1.0 g / (1.0 g + amount of solvent added g) x 100
〔表3〕より、本発明の化合物が比較化合物に比べて各溶媒に対する溶解度が高いことは明らかである。 From [Table 3], it is clear that the compound of the present invention has higher solubility in each solvent than the comparative compound.
〔実施例2−1〜2−3及び比較例2−1〕重合性組成物の調製
〔表4〕に記載の配合を行い、重合性組成物である実施例2−1〜2−3及び比較例2−1の重合性組成物を得た。〔表4〕中の各成分の符号は、下記の成分を表す。
A−1 化合物No.1
A−2 化合物No.2
A−3 化合物No.3
A’−1 比較化合物No.1
B−1 EPPN−201
(フェノールノボラック型エポキシ樹脂、エポキシ当量193g/eq.、日本化薬社製)
B−2 TRR−5010G
(クレゾールノボラック型フェノール樹脂、水酸基当量120g/eq.、Mw=8,000、旭有機材工業社製)
C−1 FZ−2122
(ポリエーテル変性ポリシロキサン、東レダウコーニング社製)
D−1 シクロペンタノン (溶剤)[Examples 2-1 to 2-3 and Comparative Example 2-1] Preparation of Polymerizable Compositions Examples 2-1 to 2-3 and Examples 2-1 to 2-3, which are polymerizable compositions by formulating the formulations shown in [Table 4]. A polymerizable composition of Comparative Example 2-1 was obtained. The reference numerals of each component in [Table 4] represent the following components.
A-1 Compound No. 1
A-2 Compound No. 2
A-3 Compound No. 3
A'-1 Comparative Compound No. 1
B-1 EPPN-201
(Phenol novolac type epoxy resin, epoxy equivalent 193 g / eq., Made by Nippon Kayaku Co., Ltd.)
B-2 TRR-5010G
(Cresol novolac type phenol resin, hydroxyl group equivalent 120 g / eq., Mw = 8,000, manufactured by Asahi Organic Materials Industry Co., Ltd.)
C-1 FZ-2122
(Polyether-modified polysiloxane, manufactured by Toray Dow Corning)
D-1 Cyclopentanone (solvent)
〔評価2〕重合性組成物及び硬化物の評価
上記で得られた実施例2−1〜2−3及び比較例2−1の重合性組成物について、線幅感度、硬化物の残膜率の評価を、下記の手順で行った。結果を〔表5〕に併記する。[Evaluation 2] Evaluation of Polymerizable Composition and Cured Product Regarding the polymerizable compositions of Examples 2-1 to 2-3 and Comparative Example 2-1 obtained above, the line width sensitivity and the residual film ratio of the cured product Was evaluated according to the following procedure. The results are also shown in [Table 5].
[評価サンプルの作成方法及び評価方法]
実施例2−1〜2−3及び比較例2−1の重合性組成物(各組成物の塗布量約2.0cc)をそれぞれ、ガラス基材にスピンコーター(500rpm×2秒→1800rpm×15秒→slope×5秒)で塗膜し、ホットプレート上でプリベイクをした(90℃×120秒)。
その後、トプコン露光機を用い紫外光を分割露光した(60,120mJ/cm2、gap:20μm、照度:20.0mW/cm2)。
露光後、ホットプレート上でポストベイクを行った(120℃×5分)後、PGMEA(温度:23℃)で現像した:200rpm×10秒→IPA(イソプロピルアルコール)洗浄(200rpm×10秒→乾燥:500rpm×5秒)。
得られたサンプルについて、各露光量におけるマスク開口20μmのパターンの線幅・残膜率を測定した。[How to create and evaluate evaluation samples]
A spin coater (500 rpm × 2 seconds → 1800 rpm × 15) was applied to each of the polymerizable compositions of Examples 2-1 to 2-3 and Comparative Example 2-1 (coating amount of each composition was about 2.0 cc) on a glass substrate. The coating film was applied in seconds → slope × 5 seconds) and prebaked on a hot plate (90 ° C. × 120 seconds).
Then, ultraviolet light was dividedly exposed using a Topcon exposure machine (60,120 mJ / cm 2 , gap: 20 μm, illuminance: 20.0 mW / cm 2 ).
After exposure, post-baking was performed on a hot plate (120 ° C. x 5 minutes), and then developed with PGMEA (temperature: 23 ° C.): 200 rpm x 10 seconds → IPA (isopropyl alcohol) washing (200 rpm × 10 seconds → drying: 500 rpm x 5 seconds).
For the obtained sample, the line width and residual film ratio of the pattern with a mask opening of 20 μm were measured at each exposure amount.
〔表5〕のとおり、本発明の重合性組成物は、比較重合性組成物と比較して、大きな線幅(高感度)、高い残膜率(硬化性が高い)を示した。このことから、本発明の化合物が重合開始剤として優れていることは明白である。 As shown in [Table 5], the polymerizable composition of the present invention showed a large line width (high sensitivity) and a high residual film ratio (high curability) as compared with the comparative polymerizable composition. From this, it is clear that the compound of the present invention is excellent as a polymerization initiator.
〔評価3〕光分解性試験(実施例3−1〜3−3、比較例3−1)
上記化合物No.1〜No.3及び比較化合物No.1を、1.0×10−4mol濃度のアセトニトリル溶液に調製して蓋付き石英セルに入れた。これらのサンプルそれぞれに超高圧水銀ランプを光源とする光を100mJ/cm2、500mJ/cm2及び1000mJ/cm2(365nmにおける積算光量)の条件で照射し、分解性を調べた。分解性の評価には、HPLCを用いて該当化合物に由来する光未照射時のピーク面積と光照射後のピーク面積を測定し、下記の計算式より分解率を計算した。得られた分解率を下記〔表6〕に記載した。
分解率(%)=[(光未照射時のHPLC面積)―(光照射後のHPLC面積)]/
(光未照射時のHPLC面積)×100
[Evaluation 3] Photodegradability test (Examples 3-1 to 3-3, Comparative Example 3-1)
The above compound No. 1-No. 3 and Comparative Compound No. 1 was prepared in an acetonitrile solution having a concentration of 1.0 × 10 -4 mol and placed in a quartz cell with a lid. Each of these samples was irradiated with light from an ultra-high pressure mercury lamp as a light source under the conditions of 100 mJ / cm 2 , 500 mJ / cm 2 and 1000 mJ / cm 2 (integrated light intensity at 365 nm), and the degradability was examined. For the evaluation of degradability, the peak area of the compound derived from the compound before light irradiation and the peak area after light irradiation were measured, and the decomposition rate was calculated from the following formula. The obtained decomposition rates are shown in [Table 6] below.
Decomposition rate (%) = [(HPLC area without light irradiation)-(HPLC area after light irradiation)] /
(HPLC area when not irradiated with light) x 100
〔表6〕の結果から、本発明の化合物が比較化合物に比べて分解率が高く、感度に優れていることは明らかである。 From the results in [Table 6], it is clear that the compound of the present invention has a higher decomposition rate and excellent sensitivity as compared with the comparative compound.
Claims (17)
R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ独立に、水素原子、シアノ基、ニトロ基、−OR11、−COOR11、−CO−R11、−SR11、ハロゲン原子、炭素原子数1〜20の脂肪族炭化水素基、炭素原子数6〜20の芳香族炭化水素基、炭素原子数2〜20の複素環を含有する基又は下記式(II)で表される基を表し、
R11は、炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基を表し、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10及びR11で表される基中の水素原子の1つ又は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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換される場合があり、
R3、R4、R5、R6、R7、R8、R9及びR10のうち1つ以上が下記式(II)で表される基である。
X1は、−NR22R23、下記式(a)又は下記式(b)で表される基であり、
R22及びR23は、それぞれ独立に、水素原子、炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基であるか、
R22とR23が、互いに連結して、窒素原子及び炭素原子からなる環、又は酸素原子、窒素原子及び炭素原子からなる環であり、
R21、R22及びR23で表される基中の水素原子の1つ又は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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換される場合があり、
nは、0又は1を表し、*は結合手を表す。
R31とR32、R33とR34、R35とR36、R37とR38及びR39とR40が、互いに連結して、窒素原子及び炭素原子からなる環、又は酸素原子、窒素原子及び炭素原子からなる環を形成する場合があり、
R31、R32、R33、R34、R35、R36、R37、R38、R39及びR40で表される基中の水素原子の1つ又は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、イソシアネート基又は炭素原子数2〜20の複素環を含有する基で置換される場合があり、
*は結合手を表す。A carbamoyloxime compound represented by the following formula (I).
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently hydrogen atoms, cyano groups, nitro groups, -OR 11 , -COOR 11 , -CO-R, respectively. 11 , -SR 11 , halogen atom, aliphatic hydrocarbon group having 1 to 20 carbon atoms, aromatic hydrocarbon group having 6 to 20 carbon atoms, group containing a heterocycle having 2 to 20 carbon atoms, or the following Represents the group represented by equation (II)
R 11 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
One or more of the hydrogen atoms in the groups represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are halogens. Atomic, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group, isocyanate group or group containing a heterocycle having 2 to 20 carbon atoms. May be replaced with
One or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is a group represented by the following formula (II).
X 1 is −NR 22 R 23 , a group represented by the following formula (a) or the following formula (b).
Each of R 22 and R 23 is independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
R 22 and R 23 are connected to each other and are a ring composed of a nitrogen atom and a carbon atom, or a ring composed of an oxygen atom, a nitrogen atom and a carbon atom.
One or more of the hydrogen atoms in the groups represented by R 21 , R 22 and R 23 are halogen atoms, nitro groups, cyano groups, hydroxyl groups, amino groups, carboxyl groups, methacryloyl groups, acryloyl groups and epoxy groups. , Vinyl group, vinyl ether group, mercapto group, isocyanate group or group containing a heterocycle having 2 to 20 carbon atoms may be substituted.
n represents 0 or 1, and * represents a bond.
R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38, and R 39 and R 40 are connected to each other to form a ring consisting of nitrogen and carbon atoms, or an oxygen atom and nitrogen. May form a ring of atoms and carbon atoms,
One or more of the hydrogen atoms in the group represented by R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are halogen atoms, nitro. Substituted with a group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group or a group containing a heterocycle having 2 to 20 carbon atoms. May be
* Represents a bond.
R22及びR23が、それぞれ独立に、炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基であるか、
R22が水素原子であり、R23が炭素原子数1〜20の脂肪族炭化水素基又は炭素原子数6〜20の芳香族炭化水素基であるか、
R22とR23が、互いに連結して、窒素原子及び炭素原子からなる環、又は酸素原子、窒素原子及び炭素原子からなる環を形成している、請求項1に記載のカルバモイルオキシム化合物。 X 1 in the above formula (I) represents −NR 22 R 23 , and
Whether R 22 and R 23 are independently aliphatic hydrocarbon groups having 1 to 20 carbon atoms or aromatic hydrocarbon groups having 6 to 20 carbon atoms, respectively.
Whether R 22 is a hydrogen atom and R 23 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
The carbamoyl oxime compound according to claim 1, wherein R 22 and R 23 are linked to each other to form a ring composed of a nitrogen atom and a carbon atom, or a ring composed of an oxygen atom, a nitrogen atom and a carbon atom.
R22とR23が、互いに連結して、窒素原子及び炭素原子からなる環を形成している、請求項1に記載のカルバモイルオキシム化合物。 X 1 in the above formula (I) represents −NR 22 R 23 , and
The carbamoyloxime compound according to claim 1, wherein R 22 and R 23 are linked to each other to form a ring composed of a nitrogen atom and a carbon atom.
R22とR23が、それぞれ独立に、炭素原子数1〜20の脂肪族炭化水素基である、請求項1又は2に記載のカルバモイルオキシム化合物。 X 1 in the above formula (I) represents −NR 22 R 23 , and
The carbamoyloxime compound according to claim 1 or 2, wherein R 22 and R 23 are independently aliphatic hydrocarbon groups having 1 to 20 carbon atoms.
R22が水素原子であり、R23が炭素原子数6〜20の芳香族炭化水素基である、請求項1又は2に記載のカルバモイルオキシム化合物。 X 1 in the above formula (I) represents −NR 22 R 23 , and
The carbamoyl oxime compound according to claim 1 or 2, wherein R 22 is a hydrogen atom and R 23 is an aromatic hydrocarbon group having 6 to 20 carbon atoms.
A method for producing a cured product, which comprises a step of irradiating the polymerizable composition according to claim 14 or 15 with energy rays.
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