JPWO2015083605A1 - NOVEL COMPOUND AND COMPOSITION CONTAINING THE COMPOUND - Google Patents
NOVEL COMPOUND AND COMPOSITION CONTAINING THE COMPOUND Download PDFInfo
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- JPWO2015083605A1 JPWO2015083605A1 JP2015551480A JP2015551480A JPWO2015083605A1 JP WO2015083605 A1 JPWO2015083605 A1 JP WO2015083605A1 JP 2015551480 A JP2015551480 A JP 2015551480A JP 2015551480 A JP2015551480 A JP 2015551480A JP WO2015083605 A1 JPWO2015083605 A1 JP WO2015083605A1
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- carbon atoms
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 159
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- -1 styrene compound Chemical class 0.000 claims abstract description 282
- 238000010521 absorption reaction Methods 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 28
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 211
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 57
- 125000005843 halogen group Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 239000003999 initiator Substances 0.000 abstract description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 47
- 239000000975 dye Substances 0.000 description 36
- 239000004593 Epoxy Substances 0.000 description 26
- 125000001931 aliphatic group Chemical group 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 239000000463 material Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 238000000576 coating method Methods 0.000 description 16
- 125000002723 alicyclic group Chemical group 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 238000010304 firing Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000006229 carbon black Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 0 CC1(C)C(*)=C(C)CC1 Chemical compound CC1(C)C(*)=C(C)CC1 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 5
- OSDBJMYIUDLIRI-UHFFFAOYSA-N oxo-[[1-[[4-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]cyclohexyl]oxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COC1CCC(OCN2C=CC(=C[NH+]=O)C=C2)CC1 OSDBJMYIUDLIRI-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 150000007519 polyprotic acids Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
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- 239000004305 biphenyl Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
- 229940049920 malate Drugs 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 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 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical group CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 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
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
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- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
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- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
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- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups
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- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
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- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G03F7/004—Photosensitive materials
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- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
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Abstract
本発明は、耐熱性に優れた着色感光性組成物(着色アルカリ現像性感光性組成物)の色素として好適な新規化合物及び該新規化合物を用いた着色感光性組成物を提供するものであり、具体的には、紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に下記一般式(1)で表される置換基を1〜10個有する化合物、好ましくはシアノスチレン化合物、トリアリールメタン化合物又はシアニン化合物、並びに該化合物を酸価を有するエチレン性不飽和結合を有する重合性化合物及び光ラジカル重合開始剤と共に併用した着色感光性組成物を提供するものである。一般式(1)の具体的な内容については本明細書に記載の通りである。The present invention provides a novel compound suitable as a dye for a colored photosensitive composition excellent in heat resistance (colored alkali-developable photosensitive composition) and a colored photosensitive composition using the novel compound, Specifically, it is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region and having 1 to 10 substituents represented by the following general formula (1) in the molecule, preferably cyano The present invention provides a colored photosensitive composition in which a styrene compound, a triarylmethane compound or a cyanine compound, and a polymerizable compound having an ethylenically unsaturated bond having an acid value and a radical photopolymerization initiator are used in combination. The specific contents of the general formula (1) are as described in this specification.
Description
本発明は、フェノール系酸化防止剤構造を有する有機色素化合物、及び該化合物を含有する組成物に関する。更には、該組成物を用いた、エネルギー線により重合可能な着色感光性組成物及び該着色感光性組成物を用いたカラーフィルタに関する。 The present invention relates to an organic dye compound having a phenolic antioxidant structure and a composition containing the compound. Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the composition, and a color filter that uses the colored photosensitive composition.
特定の光に対して強度の大きい吸収を有する化合物は、CD−R、DVD−R、DVD+R、BD−R等の光学記録媒体の記録層や、液晶表示装置(LCD)、プラズマディスプレイパネル(PDP)、エレクトロルミネッセンスディスプレイ(ELD)、陰極管表示装置(CRT)、蛍光表示管、電界放射型ディスプレイ等の画像表示装置の光学要素として用いられている。 Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display devices (LCD), plasma display panels (PDP). ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
液晶表示装置(LCD)、プラズマディスプレイパネル(PDP)、エレクトロルミネッセンスディスプレイ(ELD)、陰極管表示装置(CRT)、蛍光表示管、電界放射型ディスプレイ等の画像表示装置用の光学フィルタにおいては、300〜1100nmの波長の光を吸収する各種化合物が、光吸収剤として用いられている。
これらの光吸収剤には、光吸収が特別に急峻であること、即ちλmaxの半値幅が小さいこと、また光や熱等により機能が失われないことが求められている。In an optical filter for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display, etc., 300 Various compounds that absorb light having a wavelength of ˜1100 nm are used as light absorbers.
These light absorbers are required to have particularly steep light absorption, that is, having a small half-value width of λmax and not to lose its function due to light, heat, or the like.
主として液晶表示装置(LCD)に用いられる光学フィルタには、カラーフィルタがある。カラーフィルタには、一般的にRGBの3原色が用いられてきたが、単独の色材では純粋なRGBの色相を持たせることは困難であり、複数の色材を用いて純粋なRGBの色相に近づける努力がなされてきた。そのため、RGBではなく、黄色、橙色、紫色等の色材も必要とされている。
カラーフィルタに用いられる光吸収剤には、耐熱性の高さにより有機及び/又は無機顔料が用いられてきたが、顔料であるため表示装置としての輝度を低下させてしまうという問題があり、光源の輝度を高めることでこの問題を解決してきた。しかし、低消費電力化の流れに伴い、染料を用いたカラーフィルタの開発が盛んになっている。An optical filter mainly used for a liquid crystal display (LCD) includes a color filter. In general, three primary colors of RGB have been used for a color filter, but it is difficult to have a pure RGB hue with a single color material, and a pure RGB hue using a plurality of color materials. Efforts have been made to get closer to. Therefore, color materials such as yellow, orange and purple are required instead of RGB.
Organic and / or inorganic pigments have been used as light absorbers for color filters due to their high heat resistance. However, since they are pigments, there is a problem in that the luminance of a display device is lowered. This problem has been solved by increasing the brightness of the. However, with the trend toward lower power consumption, development of color filters using dyes has become active.
更に近年では、固体撮像素子に使用されるカラーフィルタにおいて、画質向上の観点から、着色パターンの薄膜化が要求されており、薄膜化するためには色濃度の点から染料濃度を高める必要がある。また、染料のモル吸収光係数が低い場合にも、多量の染料を添加する必要がある。
しかし、染料濃度を高めると、成膜後に加熱処理(ポストべーク)を施した場合に、隣接画素間や積層構造中の上下層間で混色が生じやすいため、耐熱性が要求されている。In recent years, in color filters used in solid-state imaging devices, it is required to reduce the color pattern from the viewpoint of improving the image quality, and in order to reduce the thickness, it is necessary to increase the dye concentration in terms of color density. . In addition, a large amount of dye must be added even when the molar absorption coefficient of the dye is low.
However, when the dye concentration is increased, when heat treatment (post-bake) is performed after film formation, color mixing is likely to occur between adjacent pixels or between upper and lower layers in a laminated structure, and thus heat resistance is required.
特許文献1〜3には、特定構造の有機色素を含有するカラーフィルター用着色樹脂組成物が開示されている。
また、特許文献4及び5には、色素と酸化防止剤を含有するカラーフィルター用着色組成物が開示されている。
しかし、これらの文献に記載のカラーフィルター用着色組成物に用いられる化合物は、耐熱性の点で満足できるものではなかった。Patent Documents 1 to 3 disclose a colored resin composition for a color filter containing an organic dye having a specific structure.
Patent Documents 4 and 5 disclose a coloring composition for a color filter containing a pigment and an antioxidant.
However, the compounds used in the coloring compositions for color filters described in these documents are not satisfactory in terms of heat resistance.
従って、本発明の目的は、耐熱性に優れた着色感光性組成物(着色アルカリ現像性感光性組成物)を提供することにある。また、本発明の別の目的は、上記着色感光性組成物(着色アルカリ現像性感光性組成物)を用いた光学フィルタ、特に輝度を低下させず、液晶表示パネル等の画像表示装置に好適なカラーフィルタを提供することにある。 Accordingly, an object of the present invention is to provide a colored photosensitive composition excellent in heat resistance (colored alkali-developable photosensitive composition). Another object of the present invention is an optical filter using the colored photosensitive composition (colored alkali-developable photosensitive composition), particularly suitable for an image display device such as a liquid crystal display panel without reducing luminance. It is to provide a color filter.
本発明者は、鋭意検討を重ねた結果、特定の構造を有する化合物が、耐熱性に優れることを知見し、またこの化合物を用いた着色感光性組成物(着色アルカリ現像性感光性組成物)が、光学フィルタ(特にカラーフィルタ)の輝度を低下させず、液晶表示パネル等の画像表示装置用カラーフィルタに好適であることを知見し、本発明に到達した。 As a result of extensive studies, the present inventor has found that a compound having a specific structure is excellent in heat resistance, and a colored photosensitive composition (colored alkali-developable photosensitive composition) using this compound. However, it has been found that it is suitable for a color filter for an image display device such as a liquid crystal display panel without reducing the luminance of an optical filter (particularly a color filter), and has reached the present invention.
本発明は、上記知見に基づきなされたもので、紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に下記一般式(1)で表される置換基を1〜10個有する化合物を提供するものである。 The present invention has been made on the basis of the above knowledge, and is an organic dye having an absorption maximum in the wavelength region from ultraviolet to near infrared, wherein the substituent represented by the following general formula (1) is 1 to A compound having 10 is provided.
R01、R02、R03、R04及びR05のうち少なくとも1つは−O−R1で表され、
R1は、水素原子、炭素原子数1〜40のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基、炭素原子数2〜20の複素環含有基又はトリアルキルシリル基を表し、
R01、R02、R03、R04及びR05並びにR1で表されるアルキル基、アリール基、アリールアルキル基又は複素環含有基は、置換基を有しているか又は無置換であり、
R01、R02、R03、R04及びR05並びにR1で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素−炭素二重結合、−O−、−S−、−CO−、−O−CO−、−CO−O−、−O−CO−O−、−S−CO−、−CO−S−、−S−CO−O−、−O−CO−S−、−CO−NH−、−NH−CO−、−NH−CO−O−、−NR2−、>P=O、−S−S−又は−SO2−で置き換わっていてもよく、
R2は、水素原子又は炭素原子数1〜8のアルキル基を表す。)
At least one of R 01 , R 02 , R 03 , R 04 and R 05 is represented by —O—R 1 ;
R 1 is a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a heterocycle-containing group having 2 to 20 carbon atoms, or Represents a trialkylsilyl group,
The alkyl group, aryl group, arylalkyl group or heterocyclic ring-containing group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 has a substituent or is unsubstituted,
The methylene group in the alkyl group or arylalkyl group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 is a carbon-carbon double bond, —O—, —S—, —CO. -, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH -, - NH- CO -, - NH-CO-O -, - NR 2 -,> P = O, -S-S- or -SO 2 - may be replaced by,
R 2 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. )
また、本発明は、上記の、紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に下記一般式(1)で表される置換基を1〜10個有する化合物を含有する組成物を提供するものである。 Further, the present invention is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region, and having 1 to 10 substituents represented by the following general formula (1) in the molecule The composition containing this is provided.
また、本発明は、上記組成物に、さらに酸価を有するエチレン不飽和結合を有する重合性化合物及び光ラジカル重合開始剤を含有する着色感光性組成物を提供するものである。 The present invention also provides a colored photosensitive composition containing a polymerizable compound having an ethylenically unsaturated bond having an acid value and a photoradical polymerization initiator in addition to the above composition.
特定の構造を有する化合物を含有する本発明の着色感光性組成物(着色アルカリ現像性感光性組成物)は耐熱性に優れるものである。また、その硬化物は、表示デバイス用カラーフィルタに好適なものである。 The colored photosensitive composition of the present invention (colored alkali-developable photosensitive composition) containing a compound having a specific structure is excellent in heat resistance. Moreover, the cured product is suitable for a color filter for a display device.
以下、本発明について、好ましい実施形態に基づき説明する。 Hereinafter, the present invention will be described based on preferred embodiments.
先ず、上記紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物について説明する。 First, a compound having at least one structure represented by the general formula (1) in the molecule, which is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region will be described.
上記紫外から近赤外の波長領域に吸収極大を有する有機色素としては、紫外から近赤外の波長領域、即ち380〜1200nmに吸収極大を有する化合物であれば特に限定されないが、例えば、シアノスチレン化合物、アゾ化合物、アントラキノン化合物、インジゴイド化合物、トリアリールメタン化合物、キサンテン化合物、アリザリン化合物、アクリジン化合物、スチルベン化合物、チアゾール化合物、ナフトール化合物、キノリン化合物、ニトロ化合物、インダミン化合物、オキサジン化合物、フタロシアニン化合物、シアニン化合物、ジインモニウム化合物、シアノエテニル化合物、ジシアノスチレン化合物、カルボニウム化合物、ローダミン化合物、ペリレン化合物、ポリエンナフトラクタム化合物、クマリン化合物、スクアリリウム化合物、クロコニウム化合物、スピロピラン化合物、スピロオキサジン化合物、メロシアニン化合物、オキソノール化合物、スチリル化合物、ピリリウム化合物、ローダニン化合物、オキサゾロン化合物、フタルイミド化合物、ナフタルイミド化合物、シンノリン化合物、ナフトキノン化合物、アントラキノン化合物、アザアントラキノン化合物、ポルフィリン化合物、アザポルフィリン化合物、ピロメテン化合物、キナクリドン化合物、ジケトピロロピロール化合物、インジゴ化合物、アクリジン化合物、アジン化合物、アゾメチン化合物、アニリン化合物、キノフタロン化合物、キノンイミン化合物、オリゴフェニレン化合物、イリジウム錯体化合物、ユーロピウム錯体化合物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。 The organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region is not particularly limited as long as it is a compound having an absorption maximum in the ultraviolet to near-infrared wavelength region, that is, 380 to 1200 nm. Compound, azo compound, anthraquinone compound, indigoid compound, triarylmethane compound, xanthene compound, alizarin compound, acridine compound, stilbene compound, thiazole compound, naphthol compound, quinoline compound, nitro compound, indamine compound, oxazine compound, phthalocyanine compound, cyanine Compound, diimmonium compound, cyanoethenyl compound, dicyanostyrene compound, carbonium compound, rhodamine compound, perylene compound, polyenenaphtholactam compound, coumarin compound, squaryli Compounds, croconium compounds, spiropyran compounds, spirooxazine compounds, merocyanine compounds, oxonol compounds, styryl compounds, pyrylium compounds, rhodanine compounds, oxazolone compounds, phthalimide compounds, naphthalimide compounds, cinnoline compounds, naphthoquinone compounds, anthraquinone compounds, azaanthraquinone compounds , Porphyrin compounds, azaporphyrin compounds, pyromethene compounds, quinacridone compounds, diketopyrrolopyrrole compounds, indigo compounds, acridine compounds, azine compounds, azomethine compounds, aniline compounds, quinophthalone compounds, quinoneimine compounds, oligophenylene compounds, iridium complex compounds, europium Examples include dyes such as complex compounds. Good.
上記一般式(1)で表される構造を上記紫外から近赤外の波長領域に吸収極大を有する有機色素に導入する方法としては、特に限定されず、公知の反応を応用した方法が挙げられるが、例えば、エステル化、アミド化等の反応を利用する方法が挙げられる。 The method for introducing the structure represented by the general formula (1) into the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region is not particularly limited, and examples thereof include a method using a known reaction. However, for example, a method utilizing a reaction such as esterification or amidation can be mentioned.
上記紫外から近赤外の波長領域に吸収極大を有する有機色素は、1〜10個の上記一般式(1)で表される置換基が結合した構造を有する。置換基が複数の場合は、互いに同じであっても異なっていてもよい。置換基の数は、合成の容易さの点から、好ましくは2〜6個である。 The organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region has a structure in which 1 to 10 substituents represented by the general formula (1) are bonded. When there are a plurality of substituents, they may be the same or different. The number of substituents is preferably 2 to 6 from the viewpoint of ease of synthesis.
上記一般式(1)におけるR01、R02、R03、R04及びR05で表されるハロゲン原子としては、フッ素、塩素、臭素、ヨウ素が挙げられる。
R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基としては、メチル、エチル、プロピル、iso−プロピル、ブチル、sec−ブチル、tert−ブチル、iso−ブチル、アミル、iso−アミル、tert−アミル、シクロペンチル、ヘキシル、2−ヘキシル、3−ヘキシル、シクロヘキシル、4−メチルシクロヘキシル、ヘプチル、2−ヘプチル、3−ヘプチル、iso−ヘプチル、tert−ヘプチル、1−オクチル、iso−オクチル、tert−オクチル、ノニル、イソノニル、デシル、ウンデシル、ドデシル、トリデシル、イソトリデシル、テトラデシル、ペンタデシル、ヘキサデシル、へプタデシル、オクタデシル、アダマンチル、1−アダマンチル、2−アダマンチル、2−メチル−1−アダマンチル、2−メチル−2−アダマンチル、2−エチル−1−アダマンチル、2−エチル−2−アダマンチル、2−ノルボルニル、2−ノルボルニルメチル等が挙げられ、
R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基としては、フェニル、ナフチル、アントラセニル、2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、4−ビニルフェニル、3−iso−プロピルフェニル、4−iso−プロピルフェニル、4−ブチルフェニル、4−iso−ブチルフェニル、4−tert−ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、4−ステアリルフェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ−tert−ブチルフェニル、2,5−ジ−tert−ブチルフェニル、2,6−ジ−tert−ブチルフェニル、2,4−ジ−tert−ペンチルフェニル、2,5−ジ−tert−アミルフェニル、2,5−ジ−tert−オクチルフェニル、2,4−ジクミルフェニル、4−シクロヘキシルフェニル、(1,1’−ビフェニル)−4−イル、2,4,5−トリメチルフェニル、フェロセニル等が挙げられ、
R01、R02、R03、R04及びR05並びにR1で表される炭素原子数7〜20のアリールアルキル基としては、ベンジル、フルオレニル、インデニル、9−フルオレニルメチル基、2−フェニルプロパン−2−イル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等が挙げられ、
R01、R02、R03、R04及びR05並びにR1で表される炭素原子数2〜20の複素環含有基としては、ピリジル、ピリミジル、ピリダジル、ピペリジル、ピラニル、ピラゾリル、トリアジル、ピロリル、キノリル、イソキノリル、イミダゾリル、ベンゾイミダゾリル、トリアゾリル、フリル、フラニル、ベンゾフラニル、チエニル、チオフェニル、ベンゾチオフェニル、チアジアゾリル、チアゾリル、ベンゾチアゾリル、オキサゾリル、ベンゾオキサゾリル、イソチアゾリル、イソオキサゾリル、インドリル、2−ピロリジノン−1−イル、2−ピペリドン−1−イル、2,4−ジオキシイミダゾリジン−3−イル、2,4−ジオキシオキサゾリジン−3−イル等が挙げられ、
R1で表されるトリアルキルシリル基としては、トリメチルシラン、トリエチルシラン、エチルジメチルシラン等が挙げられる。Examples of the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 in the general formula (1) include fluorine, chlorine, bromine and iodine.
R 01, R 02, the alkyl group of R 03, R 04 and R 05 and having 1 to 40 carbon atoms represented by R 1, methyl, ethyl, propyl, iso- propyl, butyl, sec- butyl, tert -Butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, nonyl, isononyl, decyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, adamantyl, 1-adamantyl, 2-adamantyl , 2-methyl 1-adamantyl, 2-methyl-2-adamantyl, 2-ethyl-1-adamantyl, 2-ethyl-2-adamantyl, 2-norbornyl, 2-norbornyl methyl and the like,
Examples of the aryl group having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include phenyl, naphthyl, anthracenyl, 2-methylphenyl, 3-methylphenyl, 4 -Methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexyl Phenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3 , 4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenol 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5- Di-tert-octylphenyl, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1′-biphenyl) -4-yl, 2,4,5-trimethylphenyl, ferrocenyl, etc.
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl group, 2- Phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and the like,
Examples of the heterocyclic group containing 2 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl and pyrrolyl. Quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinone-1- Yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyoxazolidine-3-yl and the like,
Examples of the trialkylsilyl group represented by R 1 include trimethylsilane, triethylsilane, and ethyldimethylsilane.
R01、R02、R03、R04及びR05並びにR1で表されるアルキル基、アリール基、アリールアルキル基及び複素環含有基を置換する置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2−クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4−トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t−ブトキシカルボニル、n−オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2−エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N−メチル−アニリノ、ジフェニルアミノ,ナフチルアミノ、2−ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N−ジメチルアミノカルボニルアミノ、N,N−ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t−ブトキシカルボニルアミノ、n−オクタデシルオキシカルボニルアミノ、N−メチル−メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N−ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられる。
また、R01、R02、R03、R04及びR05並びにR1で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素−炭素二重結合、−O−、−S−、−CO−、−O−CO−、−CO−O−、−O−CO−O−、−S−CO−、−CO−S−、−S−CO−O−、−O−CO−S−、−CO−NH−、−NH−CO−、−NH−CO−O−、−NR2−、>P=O、−S−S−又は−SO2−で置き換わっていてもよく、置き換わる位置及び数は、任意である。
R2で表される炭素原子数1〜8のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示したもののうち、所定の炭素原子数を満たす基等が挙げられる。 Examples of the substituent for substituting the alkyl group, aryl group, arylalkyl group and heterocyclic-containing group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include vinyl, allyl, acryl, methacryl Ethylenically unsaturated groups such as fluorine, chlorine, bromine, iodine and the like; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, Acyl groups such as pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl; acyloxy groups such as acetyloxy and benzoyloxy; amino, ethylamino, dimethyl Amino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino Acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxy Carbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxy Substituted amino groups such as nonoxycarbonylamino, sulfamoylamino, N, N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino; sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo Groups, hydroxyl groups, nitro groups, mercapto groups, imide groups, carbamoyl groups, sulfonamido groups, phosphonic acid groups, phosphoric acid groups or carboxyl groups, sulfo groups, phosphonic acid groups, and phosphoric acid group salts.
The methylene group in the alkyl group or arylalkyl group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S. -, - CO-NH -, - NH-CO -, - NH-CO-O -, - NR 2 -,> P = O, -S-S- or -SO 2 - may be replaced by, replacing The position and number are arbitrary.
Examples of the alkyl group having 1 to 8 carbon atoms represented by R 2 include R 01 , R 02 , R 03 , R 04 and R 05 and the alkyl group having 1 to 40 carbon atoms represented by R 1. Among these, groups satisfying a predetermined number of carbon atoms are exemplified.
上記一般式(1)で表される構造の中でも、R02又はR04の少なくとも一方が炭素原子数1〜40のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基又は炭素原子数2〜20の複素環含有基であるもの、R03が−O−R1であるもの、特にR1が水素原子又は炭素原子数2〜9のアルコキシカルボニル基であるもの、中でも、R1が水素原子又は炭素原子数2〜9のアルコキシカルボニル基であり、且つR02又はR04の少なくとも一方が炭素原子数1〜40のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基又は炭素原子数2〜20の複素環含有基であるもの、特に、R1が水素原子又は炭素原子数2〜9のアルコキシカルボニル基であり、且つR02又はR04の少なくとも一方が、炭素原子数1〜10のアルキル基であるものが、耐熱性の点から好ましい。
尚、炭素原子数2〜9のアルコキシカルボニル基としては、メチルオキシカルボニル、エチルオキシカルボニル、プロピルオキシカルボニル、イソプロピルオキシカルボニル、ブチルオキシカルボニル、s−ブチルオキシカルボニル、t−ブチルオキシカルボニル、イソブチルオキシカルボニル、ペンチルオキシカルボニル、イソアミルオキシカルボニル、t−アミルオキシカルボニル、ヘキシルオキシカルボニル、シクロヘキシルオキシカルボニル、シクロヘキシルメチルオキシカルボニル、テトラヒドロフラニルオキシカルボニル、テトラヒドロピラニルオキシカルボニル等が挙げられる。Among the structures represented by the general formula (1), at least one of R 02 or R 04 is an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, or 7 to 20 carbon atoms. An arylalkyl group or a group containing 2 to 20 carbon atoms in a heterocyclic ring, one in which R 03 is —O—R 1 , particularly R 1 is a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms. In particular, R 1 is a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms, and at least one of R 02 or R 04 is an alkyl group having 1 to 40 carbon atoms, having 6 to 20 carbon atoms. An aryl group, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic-containing group having 2 to 20 carbon atoms, in particular, R 1 is a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms; and R 02 or R 04 At least one of those is an alkyl group having 1 to 10 carbon atoms are preferred from the viewpoint of heat resistance.
Examples of the alkoxycarbonyl group having 2 to 9 carbon atoms include methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl, s-butyloxycarbonyl, t-butyloxycarbonyl, isobutyloxycarbonyl Pentyloxycarbonyl, isoamyloxycarbonyl, t-amyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, cyclohexylmethyloxycarbonyl, tetrahydrofuranyloxycarbonyl, tetrahydropyranyloxycarbonyl and the like.
上記紫外から近赤外の波長領域に吸収極大を有する有機色素として例示したものの中でも、合成の容易さ及び分子設計の点から、シアノスチレン化合物、トリアリールメタン化合物、シアニン化合物が好ましい。 Among those exemplified as the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region, a cyanostyrene compound, a triarylmethane compound, and a cyanine compound are preferable from the viewpoint of ease of synthesis and molecular design.
上記シアノスチレン化合物の中でも、合成の容易さ及び分子設計の点から、下記一般式(2)で表されるものが好ましい。 Among the above cyanostyrene compounds, those represented by the following general formula (2) are preferable from the viewpoint of ease of synthesis and molecular design.
R5は、水素原子、フェニル基、シアノ基、ニトロ基、ハロゲン原子、炭素原子数1〜8のアルキル基、炭素原子数1〜8のアルコキシ基、炭素原子数1〜8のハロゲン化アルキル基又は炭素原子数1〜8のハロゲン化アルコキシ基を表し、
Yは、シアノ基又は−COOR8を表し、
R8は、水素原子、炭素原子数1〜8のアルキル基又は上記一般式(1)で表される置換基を表し、
R8で表されるアルキル基中のメチレン基は、−COO−、−O−、−OCO−、−NHCO−、−NH−又は−CONH−で置き換わっていてもよく、
Xは、単結合、窒素原子、−NR9−、酸素原子、硫黄原子、リン原子、−PR10−又は下記<1>〜<5>の何れかの条件を満たす有機基であり、且つ、Yが−COOR8で表されるときのR8、A、R6又はR7の何れか1つ以上と結合しており、
R6、R7、R9及びR10は、それぞれ独立に、水素原子、炭素原子数1〜8のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基又は上記一般式(1)で表される置換基を表し、
R6、R7、R9及びR10で表されるアルキル基、アリール基及びアリールアルキル基は、上記一般式(1)で表される置換基、ハロゲン原子、水酸基又はニトロ基で置換されていてもよく、
R6、R7、R9及びR10で表されるアルキル基及びアリールアルキル基中のメチレン基は、−COO−、−O−、−OCO−、−NHCO−、−NH−又は−CONH−で置き換わっていてもよく、
mは、1〜6の整数であり、
分子内に上記一般式(1)で表される置換基を少なくとも一つ有する。)
R 5 is a hydrogen atom, a phenyl group, a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a halogenated alkyl group having 1 to 8 carbon atoms. Or a halogenated alkoxy group having 1 to 8 carbon atoms,
Y represents a cyano group or —COOR 8 ;
R 8 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a substituent represented by the general formula (1),
The methylene group in the alkyl group represented by R 8 may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—,
X is a single bond, a nitrogen atom, —NR 9 —, an oxygen atom, a sulfur atom, a phosphorus atom, —PR 10 —, or an organic group that satisfies any of the following <1> to <5>, and Bonded to any one or more of R 8 , A, R 6 or R 7 when Y is represented by -COOR 8 ;
R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. Or the substituent represented by the said General formula (1) is represented,
The alkyl group, aryl group and arylalkyl group represented by R 6 , R 7 , R 9 and R 10 are substituted with a substituent represented by the above general formula (1), a halogen atom, a hydroxyl group or a nitro group. You can,
The methylene group in the alkyl group and arylalkyl group represented by R 6 , R 7 , R 9 and R 10 is —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—. May be replaced with
m is an integer of 1 to 6,
It has at least one substituent represented by the general formula (1) in the molecule. )
<1>m=2であり、Xが下記一般式(3)で表される。 <1> m = 2, and X is represented by the following general formula (3).
X1で表される脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、
Z1及びZ2は、それぞれ独立に、直接結合、−O−、−S−、−SO2−、−SO−、−NR13−、−PR14−を表し、
R13及びR14は、それぞれ独立に、水素原子、炭素原子数1〜8のアルキル基、炭素原子数6〜20のアリール基又は炭素原子数7〜20のアリールアルキル基を表し、
R13及びR14で表されるアルキル基、アリール基及びアリールアルキル基は、ハロゲン原子、水酸基又はニトロ基で置換されていてもよく、
R13及びR14で表されるアルキル基及びアリールアルキル基中のメチレン基は、−COO−、−O−、−OCO−、−NHCO−、−NH−又は−CONH−で置き換わっていてもよい。
但し、上記一般式(3)で表される基は炭素原子数1〜35の範囲内である。)
The methylene group in the aliphatic hydrocarbon group represented by X 1 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof. Well,
Z 1 and Z 2 each independently represent a direct bond, —O—, —S—, —SO 2 —, —SO—, —NR 13 —, —PR 14 —,
R 13 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
The alkyl group, aryl group and arylalkyl group represented by R 13 and R 14 may be substituted with a halogen atom, a hydroxyl group or a nitro group,
The methylene group in the alkyl group and arylalkyl group represented by R 13 and R 14 may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—. .
However, the group represented by the general formula (3) is in the range of 1 to 35 carbon atoms. )
R22は炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基、炭素原子数2〜10のアルケニル基又はハロゲン原子を表し、
R21及びR22で表されるアルキル基、アルコキシ基及びアルケニル基は、ハロゲン原子で置換されているか又は無置換であり、
dは0〜5の整数である。)
R 22 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom,
The alkyl group, alkoxy group and alkenyl group represented by R 21 and R 22 are substituted with a halogen atom or unsubstituted,
d is an integer of 0-5. )
R23及びR24で表されるアルキル基、アリール基、アリールオキシ基、アリールチオ基、アリールアルケニル基、アリールアルキル基及び複素環含有基は、ハロゲン原子で置換されているか又は無置換であり、
R23及びR24で表されるアルキル基及びアリールアルキル基中のメチレン基は、不飽和結合、−O−又は−S−で置き換わっていてもよく、
R23は、隣接するR23同士で環を形成していてもよく、
eは0〜4の数を表し、fは0〜8の数を表し、gは0〜4の数を表し、hは0〜4の数を表し、gとhの数の合計は2〜4である。)
The alkyl group, aryl group, aryloxy group, arylthio group, arylalkenyl group, arylalkyl group and heterocyclic group-containing group represented by R 23 and R 24 are substituted with a halogen atom or unsubstituted,
The methylene group in the alkyl group and arylalkyl group represented by R 23 and R 24 may be replaced with an unsaturated bond, —O— or —S—,
R 23 may form a ring with adjacent R 23 ,
e represents a number from 0 to 4, f represents a number from 0 to 8, g represents a number from 0 to 4, h represents a number from 0 to 4, and the total number of g and h is 2 to 2. 4. )
<2>m=3であり、Xが下記一般式(4)で表される。 <2> m = 3, and X is represented by the following general formula (4).
R25は、水素原子、炭素原子数1〜8のアルキル基、炭素原子数6〜20のアリール基又は炭素原子数7〜20のアリールアルキル基を表し、
X2で表される脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、
Z1〜Z3は、それぞれ独立に、上記一般式(3)におけるZ1及びZ2で表される基と同じである。
但し、上記一般式(4)で表わされる基は炭素原子数1〜35の範囲内である。)
R 25 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms,
The methylene group in the aliphatic hydrocarbon group represented by X 2 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof. Well,
Z 1 to Z 3 are each independently the same as the groups represented by Z 1 and Z 2 in the general formula (3).
However, the group represented by the general formula (4) is in the range of 1 to 35 carbon atoms. )
<3>m=4であり、Xが下記一般式(5)で表される。 <3> m = 4, and X is represented by the following general formula (5).
X3で表される脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、
Z1〜Z4は、それぞれ独立に、上記一般式(3)におけるZ1及びZ2で表される基と同じである。
但し、上記一般式(5)で表される基は炭素原子数1〜35の範囲内である。)
The methylene group in the aliphatic hydrocarbon group represented by X 3 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof. Well,
Z 1 to Z 4 are each independently the same as the groups represented by Z 1 and Z 2 in the general formula (3).
However, the group represented by the general formula (5) is in the range of 1 to 35 carbon atoms. )
<4>m=5であり、Xが下記一般式(6)で表される。 <4> m = 5, and X is represented by the following general formula (6).
X4で表される脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、
Z1〜Z5は、それぞれ独立に、上記一般式(3)におけるZ1及びZ2で表される基と同じである。
但し上記一般式(6)で表される基は炭素原子数2〜35の範囲内である。)
The methylene group in the aliphatic hydrocarbon group represented by X 4 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof. Well,
Z 1 to Z 5 are each independently the same as the groups represented by Z 1 and Z 2 in the general formula (3).
However, the group represented by the general formula (6) is in the range of 2 to 35 carbon atoms. )
<5>m=6であり、Xが下記一般式(7)で表される。 <5> m = 6, and X is represented by the following general formula (7).
X5で表される脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、
Z1〜Z6は、それぞれ独立に、上記一般式(3)におけるZ1及びZ2で表される基と同じである。
但し上記一般式(7)で表される基は炭素原子数2〜35の範囲内である。)
The methylene group in the aliphatic hydrocarbon group represented by X 5 is replaced with —O—, —S—, —CO—, —COO—, —OCO—, —NH— or a combination thereof. Well,
Z 1 to Z 6 are each independently the same as the groups represented by Z 1 and Z 2 in the general formula (3).
However, the group represented by the general formula (7) is in the range of 2 to 35 carbon atoms. )
上記一般式(2)におけるAで表されるベンゼン環、ナフタレン環及びアントラセンを置換していてもよいハロゲン原子、R5で表されるハロゲン原子、並びにR6、R7、R9及びR10で表されるアルキル基、アリール基及びアリールアルキル基を置換していてもよいハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられ、
Aで表されるベンゼン環、ナフタレン環及びアントラセンを置換していてもよい炭素原子数1〜8のアルキル基、及びR5〜R10で表される炭素原子数1〜8のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示した基のうち、所定の炭素数を満たす基等が挙げられ、
Aで表されるベンゼン環、ナフタレン環及びアントラセンを置換してもよい炭素原子数1〜8のアルコキシ基及びR5で表される炭素原子数1〜8のアルコキシ基としては、メトキシ、エトキシ、プロピルオキシ、イソプロピルオキシ、ブチルオキシ、s−ブチルオキシ、t−ブチルオキシ、イソブチルオキシ、ペンチルオキシ、イソアミルオキシ、t−アミルオキシ、ヘキシルオキシ、シクロヘキシルオキシ、シクロヘキシルメチルオキシ、テトラヒドロフラニルオキシ、テトラヒドロピラニルオキシ等が挙げられ、
Aで表されるベンゼン環、ナフタレン環及びアントラセンを置換していてもよい炭素原子数1〜8のハロゲン化アルキル基及びR5で表される炭素原子数1〜8のハロゲン化アルキル基としては、上述した炭素原子数1〜8のアルキル基の少なくとも1つの水素原子が上述したハロゲン原子により置換されたもの、例えば、クロロメチル、ジクロロメチル、トリクロロメチル、フルオロメチル、フルオロメチル、トリフルオロメチル、ノナフルオロブチル等が挙げられ、
Aで表されるベンゼン環、ナフタレン環及びアントラセンを置換していてもよい炭素原子数1〜8のハロゲン化アルコキシ基及びR5で表される炭素原子数1〜8のハロゲン化アルコキシ基としては、上述した炭素原子数1〜8のアルコキシ基の少なくとも1つの水素原子が上述したハロゲン原子により置換されたもの、例えば、クロロメチルオキシ、ジクロロメチルオキシ、トリクロロメチルオキシ、フルオロメチルオキシ、フルオロメチルオキシ、トリフルオロメチルオキシ、ノナフルオロブチルオキシ等が挙げられ、
R6、R7、R9及びR10で表される炭素原子数6〜20のアリール基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基として例示した基が挙げられ、
R6、R7、R9及びR10で表される炭素原子数7〜20のアリールアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数7〜20のアリールアルキル基として例示した基が挙げられる。In the above general formula (2), the benzene ring represented by A, the naphthalene ring and the halogen atom which may be substituted for the anthracene, the halogen atom represented by R 5 , and R 6 , R 7 , R 9 and R 10 As the halogen atom that may be substituted for the alkyl group, aryl group, and arylalkyl group represented by the above, the groups exemplified as the halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 Named,
Examples of the alkyl group having 1 to 8 carbon atoms that may be substituted for the benzene ring, naphthalene ring and anthracene represented by A, and the alkyl group having 1 to 8 carbon atoms represented by R 5 to R 10 R 01 , R 02 , R 03 , R 04 and R 05 , and groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 1 include groups satisfying a predetermined carbon number, and the like.
Examples of the alkoxy group having 1 to 8 carbon atoms and the alkoxy group having 1 to 8 carbon atoms represented by R 5 which may substitute the benzene ring, naphthalene ring and anthracene represented by A include methoxy, ethoxy, Propyloxy, isopropyloxy, butyloxy, s-butyloxy, t-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, t-amyloxy, hexyloxy, cyclohexyloxy, cyclohexylmethyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, etc. And
As the halogenated alkyl group having 1 to 8 carbon atoms and the halogenated alkyl group having 1 to 8 carbon atoms represented by R 5, which may be substituted for the benzene ring, naphthalene ring and anthracene represented by A, , Wherein at least one hydrogen atom of the alkyl group having 1 to 8 carbon atoms is substituted by the halogen atom described above, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, fluoromethyl, trifluoromethyl, Nonafluorobutyl and the like,
As the halogenated alkoxy group having 1 to 8 carbon atoms and the halogenated alkoxy group having 1 to 8 carbon atoms represented by R 5, which may be substituted for the benzene ring, naphthalene ring and anthracene represented by A, , Wherein at least one hydrogen atom of the alkoxy group having 1 to 8 carbon atoms is substituted by the halogen atom described above, for example, chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, fluoromethyloxy , Trifluoromethyloxy, nonafluorobutyloxy and the like,
Examples of the aryl group having 6 to 20 carbon atoms represented by R 6 , R 7 , R 9 and R 10 include carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1. The group illustrated as an aryl group of several 6-20 is mentioned,
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 6 , R 7 , R 9 and R 10 include carbons represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1. The group illustrated as an arylalkyl group of 7-20 atoms is mentioned.
上記一般式(3)におけるX1で表される二価の炭素原子数1〜35の脂肪族炭化水素基としては、メタン、エタン、プロパン、iso−プロパン、ブタン、sec−ブタン、tert−ブタン、iso−ブタン、ヘキサン、2−メチルヘキサン、3−メチルヘキサン、ヘプタン、2−メチルヘプタン、3−メチルヘプタン、iso−ヘプタン、tert−ヘプタン、1−メチルオクタン、iso−オクタン、tert−オクタン、シクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン、2,4−ジメチルシクロブタン、4−メチルシクロヘキサン等の基が、Z1及びZ2で置換された二価の基が挙げられ、脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、これらを組み合わせた基とは、例えば、−COO−O−、−COO−S−、−O−OCO−、−S−OCO−、−CO−NH−、−NH−CO−等を表し、中でも、−COO−、−O−、−OCO−、−NHCO−、−NH−、−CONH−、−O−CONH−又は−NHCO−O−で置き換わっているものが好ましく、
X1で表される二価の炭素原子数3〜35の脂環式炭化水素基としては、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロデカニル、1−アダマンチル、2−アダマンチル、ノルアダマンチル、2−メチルアダマンチル、ノルボルニル、イソノルボルニル、パーヒドロナフチル、パーヒドロアントラセニル、ビシクロ[1.1.0]ブチル、ビシクロ[1.1.1]ペンチル、ビシクロ[2.1.0]ペンチル、ビシクロ[3.1.0]ヘキシル、ビシクロ[2.1.1]ヘキシル、ビシクロ[2.2.0]ヘキシル、ビシクロ[4.1.0]ヘプチル、ビシクロ[3.2.0]ヘプチル、ビシクロ[3.1.1]ヘプチル、ビシクロ[2.2.1]ヘプチル、ビシクロ[5.1.0]オクチル、ビシクロ[4.2.0]オクチル、ビシクロ[4.1.1]オクチル、ビシクロ[3.3.0]オクチル、ビシクロ[3.2.1]オクチル、ビシクロ[2.2.2]オクチル、スピロ〔4,4〕ノナニル、スピロ〔4,5〕デカニル、デカリン、トリシクロデカニル、テトラシクロドデカニル、セドロール、シクロドデカニル等の基が、Z1及びZ2で置換された二価の基等が挙げられ、
X1で表される二価の炭素原子数6〜35の芳香環含有炭化水素基としては、フェニル、ナフチル、ビフェニル等の基が、Z1及びZ2で置換された二価の基等が挙げられ、
X1で表される二価の炭素原子数2〜35の複素環含有基としては、ピリジン、ピラジン、ピペリジン、ピペラジン、ピリミジン、ピリダジン、トリアジン、ヘキサヒドロトリアジン、フラン、テトラヒドロフラン、クロマン、キサンテン、チオフェン、チオラン等の基が、Z1及びZ2で置換された二価の基が挙げられる。
これらの基はハロゲン原子、シアノ基、ニトロ基又は炭素原子数1〜8のアルコキシ基でさらに置換されていてもよい。
R13及びR14で表される炭素原子数1〜8のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示した基のうち、所定の炭素数を満たす基が挙げられ、
R13及びR14で表される炭素原子数6〜20のアリール基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基として例示した基が挙げられ、
R13及びR14で表される炭素原子数7〜20のアリールアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数7〜20のアリールアルキル基として例示した基が挙げられ、
R13及びR14で表されるアルキル基、アリール基及びアリールアルキル基を置換していてもよいハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられる。Examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 1 in the general formula (3) include methane, ethane, propane, iso-propane, butane, sec-butane, and tert-butane. , Iso-butane, hexane, 2-methylhexane, 3-methylhexane, heptane, 2-methylheptane, 3-methylheptane, iso-heptane, tert-heptane, 1-methyloctane, iso-octane, tert-octane, A divalent group in which a group such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, 2,4-dimethylcyclobutane, 4-methylcyclohexane and the like is substituted with Z 1 and Z 2 , and aliphatic hydrocarbon The methylene group in the group is -O-, -S-, -CO-, -COO-, -OCO-, -NH- or These groups may be replaced by a combination of these. Examples of the combination of these include -COO-O-, -COO-S-, -O-OCO-, -S-OCO-, and -CO-NH. -, -NH-CO-, etc., among which -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O- are replaced. Is preferred,
Examples of the divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by X 1 include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2-adamantyl, noradamantyl, 2- Methyl adamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [3 .1.0] hexyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.0] hexyl, bicyclo [4.1.0] heptyl, bicyclo [3.2.0] heptyl, bicyclo [3 1.1] heptyl, bicyclo [2.2.1] heptyl, bicyclo [5.1.0] octyl, bicyclo [4. .0] octyl, bicyclo [4.1.1] octyl, bicyclo [3.3.0] octyl, bicyclo [3.2.1] octyl, bicyclo [2.2.2] octyl, spiro [4,4 ] Nonanyl, spiro [4,5] decanyl, decalin, tricyclodecanyl, tetracyclododecanyl, cedrol, cyclododecanyl, etc., divalent groups substituted with Z 1 and Z 2 ,
Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by X 1 include a divalent group in which a group such as phenyl, naphthyl, and biphenyl is substituted with Z 1 and Z 2. Named,
The divalent heterocyclic ring-containing group having a carbon number of 2 to 35 represented by X 1, pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene And divalent groups in which a group such as thiolane is substituted with Z 1 and Z 2 .
These groups may be further substituted with a halogen atom, a cyano group, a nitro group or an alkoxy group having 1 to 8 carbon atoms.
Examples of the alkyl group having 1 to 8 carbon atoms represented by R 13 and R 14, alkyl of R 01, R 02, R 03 , R 04 and R 05 and having 1 to 40 carbon atoms represented by R 1 Among the groups exemplified as the group, groups satisfying a predetermined carbon number can be mentioned,
Examples of the aryl group having 6 to 20 carbon atoms represented by R 13 and R 14 include aryl having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1. Examples include groups exemplified as the group,
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 13 and R 14 include those having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . Groups exemplified as arylalkyl groups,
Examples of the halogen atom which may be substituted for the alkyl group, aryl group and arylalkyl group represented by R 13 and R 14 include halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 And the groups exemplified as above.
上記(3−1)で表される置換基において、R21で表されるフェニル基及び炭素原子数3〜10のシクロアルキル基を置換してもよい炭素原子数1〜10のアルキル基並びにR22で表される炭素原子数1〜10のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示した基のうち、所定の炭素数を満たす基等が挙げられ、
R21で表されるフェニル基及び炭素原子数3〜10のシクロアルキル基を置換してもよい炭素原子数1〜10のアルコキシ基並びにR22で表される炭素原子数1〜10のアルコキシ基としては、Aで表されるベンゼン環、ナフタレン環及びアントラセンを置換してもよい炭素原子数1〜8のアルコキシ基及びR5で表される炭素原子数1〜8のアルコキシ基として例示した基等が挙げられ、
R21で表される炭素原子数3〜10のシクロアルキル基としては、シクロプロピル、シクロブチル、シクロペンチル、シクロへブチル、シクロオクチル等及びこれらの基が上記炭素原子数1〜10のアルキル基若しくは炭素原子数1〜10のアルコキシ基で置換された基等が挙げられ、
R22で表される炭素原子数2〜10のアルケニル基としては、ビニル、アリル、1−プロペニル、イソプロペニル、2−ブテニル、1,3−ブタジエニル、2−ペンテニル、2−オクテニル等が挙げられ、
R22で表されるハロゲン原子、並びにR21及びR22で表されるアルキル基、アルコキシ基及びアルケニル基を置換してもよいハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられる。
尚、R22で表されるアルキル基、アルコキシ基及びアルケニル基を置換してもよいハロゲン原子の置換位置は制限されない。In the substituent represented by (3-1) above, the phenyl group represented by R 21 and the alkyl group having 1 to 10 carbon atoms which may be substituted with the cycloalkyl group having 3 to 10 carbon atoms and R Examples of the alkyl group having 1 to 10 carbon atoms represented by 22, exemplified as the alkyl group of R 01, R 02, R 03 , R 04 and R 05 and having 1 to 40 carbon atoms represented by R 1 Among the groups, groups satisfying a predetermined carbon number, etc. are mentioned,
A phenyl group represented by R 21 and an alkoxy group having 1 to 10 carbon atoms which may be substituted with a cycloalkyl group having 3 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms represented by R 22 As the groups exemplified as the benzene ring, naphthalene ring represented by A and the alkoxy group having 1 to 8 carbon atoms which may be substituted for anthracene and the alkoxy group having 1 to 8 carbon atoms represented by R 5 Etc.
Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 21 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohebutyl, cyclooctyl and the like, and these groups are the above alkyl groups having 1 to 10 carbon atoms or carbon Groups substituted with an alkoxy group having 1 to 10 atoms, and the like.
Examples of the alkenyl group having 2 to 10 carbon atoms represented by R 22 include vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl and the like. ,
Examples of the halogen atom represented by R 22 and the halogen atom that may substitute the alkyl group, alkoxy group and alkenyl group represented by R 21 and R 22 include R 01 , R 02 , R 03 , R 04 and group exemplified as the halogen atom represented by R 05 can be mentioned.
The substitution position of the halogen atom that may substitute the alkyl group, alkoxy group and alkenyl group represented by R 22 is not limited.
上記(3−3)で表される置換基において、R23及びR24で表される炭素原子数1〜10のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示した基のうち、所定の炭素数を満たす基等が挙げられ、
R23及びR24で表される炭素原子数6〜20のアリール基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基として例示した基等が挙げられ、
R23及びR24で表される炭素原子数6〜20のアリールオキシ基としては、フェニルオキシ、ナフチルオキシ、2−メチルフェニルオキシ、3−メチルフェニルオキシ、4−メチルフェニルオキシ、4−ビニルフェニル二オキシ、3−iso−プロピルフェニルオキシ、4−iso−プロピルフェニルオキシ、4−ブチルフェニルオキシ、4−tert−ブチルフェニルオキシ、4−へキシルフェニルオキシ、4−シクロヘキシルフェニルオキシ、4−オクチルフェニルオキシ、4−(2−エチルヘキシル)フェニルオキシ、2,3−ジメチルフェニルオキシ、2,4−ジメチルフェニルオキシ、2,5−ジメチルフェニルオキシ、2.6−ジメチルフェニルオキシ、3.4−ジメチルフェニルオキシ、3.5−ジメチルフェニルオキシ、2,4−ジーtert−ブチルフェニルオキシ、2,5−ジーtert−ブチルフェニルオキシ、2,6−ジーtert−ブチルフェニルオキシ、2.4−ジーtert−ペンチルフェニルオキシ、2,5−tert−アミルフェニルオキシ、4−シクロへキシルフェニルオキシ、2,4,5−トリメチルフェニルオキシ、フェロセニルオキシ等の基及びこれらの基がハロゲン原子で置換された基等が奉げられ、
R23及びR24で表される炭素原子数6〜20のアリールチオ基としては、上記ハロゲン原子で置換されていてもよい炭素原子数6〜20のアリールオキシ基の酸素原子を硫黄原子に置換した基等が奉げられ、
R23及びR24で表される炭素原子数8〜20のアリールアルケニル基としては、上記ハロゲン原子で置換されていてもよい炭素原子数6−20のアリールオキシ基の酸素原子をビニル、アリル、1−プロペニル、イソプロペニル、2−ブテニル、1,3−ブタジエニル、2−ペンテニル、2−オクテニル等のアルケニル基で置換した基等が挙げられ、
R23及びR24で表される炭素原子数7〜20のアリールアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数7〜20のアリールアルキル基として例示した基等が挙げられる。
R23及びR24で表される炭素原子数2〜20の複素環含有基としては、ピリジン、ピラジン、ピペリジン、ピペラジン、ピリミジン、ピリダジン、トリアジン、ヘキサヒドロトリアジン、フラン、テトラヒドロフラン、クロマン、キサンテン、チオフェン、チオフラン等の基及びこれらの基がハロゲン原子で置換された基等が挙げられる。
R13及びR14で表されるアルキル基、アリール基、アリールオキシ基、アリールチオ基、アリールアルケニル基、アリールアルキル基及び複素環含有基を置換していてもよいハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられる。In the substituent represented by (3-3) above, the alkyl group having 1 to 10 carbon atoms represented by R 23 and R 24 includes R 01 , R 02 , R 03 , R 04 and R 05 , and Among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 1 , a group satisfying a predetermined carbon number, and the like can be mentioned.
Examples of the aryl group having 6 to 20 carbon atoms represented by R 23 and R 24 include aryl having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1. Examples include groups exemplified as the group,
Examples of the aryloxy group having 6 to 20 carbon atoms represented by R 23 and R 24 include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4-vinylphenyl. 2-oxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hexylphenyloxy, 4-cyclohexylphenyloxy, 4-octylphenyl Oxy, 4- (2-ethylhexyl) phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2.6-dimethylphenyloxy, 3.4-dimethylphenyl Oxy, 3.5-dimethylphenyloxy, 2 4-di-tert-butylphenyloxy, 2,5-di-tert-butylphenyloxy, 2,6-di-tert-butylphenyloxy, 2.4-di-tert-pentylphenyloxy, 2,5-tert-amylphenyl Groups such as oxy, 4-cyclohexylphenyloxy, 2,4,5-trimethylphenyloxy, ferrocenyloxy, etc., and groups in which these groups are substituted with halogen atoms, etc.
As the arylthio group having 6 to 20 carbon atoms represented by R 23 and R 24 , the oxygen atom of the aryloxy group having 6 to 20 carbon atoms which may be substituted with the halogen atom is substituted with a sulfur atom. The foundations are dedicated,
As the arylalkenyl group having 8 to 20 carbon atoms represented by R 23 and R 24 , the oxygen atom of the aryloxy group having 6 to 20 carbon atoms which may be substituted with the halogen atom is vinyl, allyl, Groups substituted with alkenyl groups such as 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, and the like,
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 23 and R 24 include those having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . The group etc. which were illustrated as an arylalkyl group are mentioned.
Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 23 and R 24 include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene. And groups such as thiofuran and groups in which these groups are substituted with a halogen atom.
Examples of the halogen atom that may be substituted for the alkyl group, aryl group, aryloxy group, arylthio group, arylalkenyl group, arylalkyl group, and heterocyclic group represented by R 13 and R 14 include R 01 , R The groups exemplified as the halogen atoms represented by 02 , R 03 , R 04 and R 05 can be mentioned.
上記一般式(4)におけるX2で表される三価の炭素原子数1〜35の脂肪族炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂肪族炭化水素基が、Z1、Z2及びZ3で置換された三価の基等が挙げられ、脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−CO−O−、−O−CO−、−SO2−、−NH−又はこれらを組み合わせた基で置き換わってもよく、これらを組み合わせた基とは、例えば、−COO−O−、−COO−S−、−O−OCO−、−S−OCO−、−CO−NH−、−NH−CO−等を表し、中でも、−COO−、−O−、−OCO−、−NHCO−、−NH−、−CONH−、−O−CONH−又は−NHCO−O−で置き換わっているものが好ましく、 X2で表される三価の炭素原子数3〜35の脂環式炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂環式炭化水素基が、Z1、Z2及びZ3で置換された三価の基等が挙げられ、
X2で表される三価の炭素原子数6〜35の芳香環含有炭化水素基としては、上記一般式(3)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2及びZ3で置換された三価の基等が挙げられ、
X2で表される三価の炭素原子数2〜35の複素環含有基としては、上記一般式(3)におけるX1の説明で例示した複素環含有基が、Z1、Z2及びZ3で置換された三価の基等が挙げられる。
また、R25で表される炭素原子数1〜8のアルキル基、炭素原子数6〜20のアリール基又は炭素原子数7〜20のアリールアルキル基としては、R13及びR14で表される炭素原子数1〜8のアルキル基、炭素原子数6〜20のアリール基又は炭素原子数7〜20のアリールアルキル基と同様の基等が挙げられる。Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 2 in the general formula (4) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3). Are trivalent groups substituted with Z 1 , Z 2 and Z 3 , and the methylene group in the aliphatic hydrocarbon group is —O—, —S—, —CO—, —CO—O. —, —O—CO—, —SO 2 —, —NH—, or a combination thereof may be replaced by, for example, —COO—O—, —COO—S—, -O-OCO-, -S-OCO-, -CO-NH-, -NH-CO-, etc., among others, -COO-, -O-, -OCO-, -NHCO-, -NH-,- CONH -, - O-CONH- or preferably one is replaced with -NHCO-O-, trivalent represented by X 2 The alicyclic hydrocarbon group having a carbon number of 3 to 35, an alicyclic hydrocarbon groups exemplified in the description of X 1 in the general formula (3) is substituted with Z 1, Z 2 and Z 3 Trivalent groups, etc.
As the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by X 2 , the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And trivalent groups substituted with Z 2 and Z 3 , etc.
The trivalent heterocyclic containing group having a carbon number of 2 to 35 represented by X 2, the heterocyclic ring-containing groups exemplified in the description of X 1 in the general formula (3), Z 1, Z 2 and Z And trivalent groups substituted with 3 .
The alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 20 carbon atoms, or the arylalkyl group having 7 to 20 carbon atoms represented by R 25 is represented by R 13 and R 14. Examples thereof include a group similar to an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.
上記一般式(5)におけるX3で表される四価の炭素原子数1〜35の脂肪族炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂肪族炭化水素基が、Z1、Z2、Z3及びZ4で置換された四価の基等が挙げられ、脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、これらを組み合わせた基とは、例えば、−COO−O−、−COO−S−、−O−OCO−、−S−OCO−、−CO−NH−、−NH−CO−等を表し、中でも、−COO−、−O−、−OCO−、−NHCO−、−NH−、−CONH−、−O−CONH−又は−NHCO−O−で置き換わっているものが好ましく、
X3で表される四価の炭素原子数3〜35の脂環式炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂環式炭化水素基が、Z1、Z2、Z3及びZ4で置換された三価の基等が挙げられ、
X3で表される四価の炭素原子数6〜35の芳香環含有炭化水素基としては、上記一般式(3)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2、Z3及びZ4で置換された四価の基等が挙げられ、
X3で表される四価の炭素原子数2〜35の複素環含有基としては、上記一般式(3)におけるX1の説明で例示した複素環含有基が、Z1、Z2、Z3及びZ4で置換された四価の基等が挙げられる。The tetravalent C1-C35 aliphatic hydrocarbon group represented by X 3 in the general formula (5) is an aliphatic hydrocarbon group exemplified in the description of X 1 in the general formula (3). Are tetravalent groups substituted with Z 1 , Z 2 , Z 3 and Z 4 , and the methylene group in the aliphatic hydrocarbon group is —O—, —S—, —CO—, — COO—, —OCO—, —NH—, or a combination thereof may be replaced with, for example, —COO—O—, —COO—S—, —O—OCO—. , -S-OCO-, -CO-NH-, -NH-CO-, etc., among them -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O Those substituted with —CONH— or —NHCO—O— are preferred,
The tetravalent alicyclic hydrocarbon group having a carbon number of 3 to 35 represented by X 3, alicyclic hydrocarbon groups exemplified in the description of X 1 in the general formula (3), Z 1, And trivalent groups substituted with Z 2 , Z 3 and Z 4 , etc.
As the tetravalent C6-C35 aromatic ring-containing hydrocarbon group represented by X 3 , the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And tetravalent groups substituted with Z 2 , Z 3 and Z 4 , etc.
The tetravalent heterocyclic containing group having a carbon number of 2 to 35 represented by X 3, heterocyclic ring-containing groups exemplified in the description of X 1 in the general formula (3), Z 1, Z 2, Z And tetravalent groups substituted with 3 and Z 4 .
上記一般式(6)におけるX4で表される五価の炭素原子数2〜35の脂肪族炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂肪族炭化水素基が、Z1、Z2、Z3、Z4及びZ5で置換された五価の基等が挙げられ、脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−CO−O−、−O−CO−、−SO2−、−NH
−又はこれらを組み合わせた基で置き換わっていてもよく、これらを組み合わせた基とは、例えば、−COO−O−、−COO−S−、−O−OCO−、−S−OCO−、−CO−NH−、−NH−CO−等を表し、中でも、−COO−、−O−、−OCO−、−NHCO−、−NH−、−CONH−、−O−CONH−又は−NHCO−O−で置き換わっているものが好ましく、
X4で表される五価の炭素原子数3〜35の脂環式炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂環式炭化水素基が、Z1、Z2、Z3、Z4及びZ5で置換された五価の基等が挙げられ、
X4で表される五価の炭素原子数6〜35の芳香環含有炭化水素基としては、上記一般式(3)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2、Z3、Z4及びZ5で置換された五価の基等が挙げられ、
X4で表される五価の炭素原子数2〜35の複素環含有基としては、上記一般式(12)におけるX1で説明で例示した複素環含有基が、Z1、Z2、Z3、Z4及びZ5で置換された五価の基等が挙げられる。Examples of the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by X 4 in the general formula (6) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3). Are pentavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 , and the methylene group in the aliphatic hydrocarbon group is —O—, —S—, —CO -, - CO-O -, - O-CO -, - SO 2 -, - NH
-Or a combination thereof may be replaced by a combination of these, for example, -COO-O-, -COO-S-, -O-OCO-, -S-OCO-, -CO -NH-, -NH-CO-, etc., among them -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O- Is preferably replaced with
As the pentavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by X 4 , the alicyclic hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And pentavalent groups substituted with Z 2 , Z 3 , Z 4 and Z 5 , etc.
As the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by X 4 , the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And pentavalent groups substituted with Z 2 , Z 3 , Z 4 and Z 5 , etc.
As the pentavalent C2-C35 heterocycle-containing group represented by X 4 , the heterocycle-containing groups exemplified in the description of X 1 in the general formula (12) are Z 1 , Z 2 , Z 3, Z 4 and Z 5 pentavalent group substituted with the like.
上記一般式(7)におけるX5で表される六価の炭素原子数2〜35の脂肪族炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂肪族炭化水素基が、Z1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基等が挙げられ、脂肪族炭化水素基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−SO2−、−NH−又はこれらを組み合わせた基で置き換わっていてもよく、これらを組み合わせた基とは、例えば、−COO−O−、−COO−S−、−O−OCO−、−S−OCO−、−CO−NH−、−NH−CO−等を表し、中でも、−COO−、−O−、−OCO−、−NHCO−、−NH−、−CONH−、−O−CONH−又は−NHCO−O−で置き換わっているものが好ましく、
X5で表される六価の炭素原子数3〜35の脂環式炭化水素基としては、上記一般式(3)におけるX1の説明で例示した脂環式炭化水素基が、Z1、Z2、Z3、Z4、Z5及びZ6で置換された五価の基等が挙げられ、
X5で表される六価の炭素原子数6〜35の芳香環含有炭化水素基としては、上記一般式(3)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基等が挙げられ、
X5で表される六価の炭素原子数2〜35の複素環含有基としては、上記一般式(3)におけるX1の説明で例示した複素環含有基が、Z1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基等が挙げられる。Examples of the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by X 5 in the general formula (7) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (3). Are hexavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , and the methylene group in the aliphatic hydrocarbon group is —O—, —S—. , —CO—, —COO—, —OCO—, —SO 2 —, —NH—, or a combination thereof may be substituted with, for example, —COO—O—, -COO-S-, -O-OCO-, -S-OCO-, -CO-NH-, -NH-CO-, etc., among others, -COO-, -O-, -OCO-, -NHCO- , -NH-, -CONH-, -O-CONH- or -NHCO-O- are preferred,
As the hexavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by X 5 , the alicyclic hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And pentavalent groups substituted with Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , etc.
As the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by X 5 , the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the general formula (3) is Z 1 , And hexavalent groups substituted with Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , etc.
As the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by X 5 , the heterocyclic group exemplified in the description of X 1 in the general formula (3) is Z 1 , Z 2 , Z 3 , a hexavalent group substituted with Z 4 , Z 5 and Z 6 , and the like.
上記一般式(2)で表される化合物の中でも、Aがベンゼン環であるもの;R5が水素原子であるもの;R6、R7又はR8が上記一般式(1)で表される置換基を有するもの;mが2のとき、Xが上記一般式(3)で表され、且つ式(3)中のX1が下記群1から選ばれる基であるもの;mが3のとき、Xが上記一般式(4)で表され、且つ式(4)中のX2が下記群2から選ばれる基であるもの;mが4のとき、Xが上記一般式(5)で表され、且つ式(5)中のX3が群3から選ばれる基であるもの;mが5のとき、Xが上記一般式(6)で表され、且つ式(6)中のX4が下記群4から選ばれる基であるもの;mが6のとき、Xが上記一般式(7)で表され、且つ式(7)中のX5が下記群5から選ばれる基であるものは、原料の入手や製造が容易であり、耐熱性が高いため好ましい。Among the compounds represented by the above general formula (2), those in which A is a benzene ring; those in which R 5 is a hydrogen atom; R 6 , R 7 or R 8 is represented by the above general formula (1) One having a substituent; when m is 2, X is represented by the general formula (3), and X 1 in the formula (3) is a group selected from the following group 1; when m is 3 , X is represented by the general formula (4), and X 2 in the formula (4) is a group selected from the following group 2; when m is 4, X is represented by the general formula (5). And X 3 in formula (5) is a group selected from group 3; when m is 5, X is represented by the above general formula (6), and X 4 in formula (6) is A group selected from the following group 4; when m is 6, X is represented by the general formula (7), and X 5 in the formula (7) is a group selected from the following group 5: , Raw material acquisition and production It is preferable because it is easy to manufacture and has high heat resistance.
上記一般式(1)で表される化合物の具体例としては、下記[化16]〜[化18]で表される化合物が挙げられるが、本発明はこれらの化合物に制限されない。 Specific examples of the compound represented by the general formula (1) include compounds represented by the following [Chemical Formula 16] to [Chemical Formula 18], but the present invention is not limited to these compounds.
上記トリアリールメタン化合物の中でも、合成の容易さ及び分子設計の点から、下記一般式(8)で表されるものが好ましい。 Among the triarylmethane compounds, those represented by the following general formula (8) are preferable from the viewpoint of ease of synthesis and molecular design.
X11は酸素原子又は硫黄原子を表し、
Y11は、炭素原子数1〜8のアルキル基、炭素原子数6〜12のアリール基、炭素原子数7〜20のアリールアルキル基を表し、
R31〜R42及びY11で表されるアルキル基、アリール基又はアリールアルキル基は、ハロゲン原子で置換されているか又は無置換であり、
R32とR43、R33とR44、R36とR45、R37とR46、R40とR47、R41とR48、R31とR32、R33とR34、R35とR36、R37とR38、R39とR40及びR41とR42は、連結して6員環を形成していてもよく、
R31とR42、R34とR35及びR38とR39は、単結合、酸素原子、硫黄原子、セレン原子、CR49R50、CO、NR51、PR52又はSO2を介して連結して環を形成していてもよく、
R43、R44、R45、R46、R47及びR48は、それぞれ独立に、炭素原子数1〜8のアルキル基、フェニル基又はベンジル基を表し、
R43〜R48で表されるアルキル基は、水酸基、ハロゲン原子、シアノ基又はニトロ基で置換されているか又は無置換であり、
R43〜R48で表されるフェニル基及びベンジル基は、炭素原子数1〜4のアルキル基、ハロゲン原子、シアノ基又はビニル基で置換されているか又は無置換であり、
R43とR44、R45とR46、及びR47とR48は、連結して3〜6員環を形成していてもよく、
Anq-はq価のアニオンを表し、qは1又は2を表し、pは電荷を中性に保つ係数を表し、
分子内に上記一般式(1)で表される置換基を少なくとも一つ有する。)
X 11 represents an oxygen atom or a sulfur atom,
Y 11 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms,
The alkyl group, aryl group or arylalkyl group represented by R 31 to R 42 and Y 11 is substituted with a halogen atom or unsubstituted,
R 32 and R 43 , R 33 and R 44 , R 36 and R 45 , R 37 and R 46 , R 40 and R 47 , R 41 and R 48 , R 31 and R 32 , R 33 and R 34 , R 35 And R 36 , R 37 and R 38 , R 39 and R 40 and R 41 and R 42 may be linked to form a 6-membered ring,
R 31 and R 42 , R 34 and R 35 and R 38 and R 39 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 49 R 50 , CO, NR 51 , PR 52 or SO 2. To form a ring,
R 43 , R 44 , R 45 , R 46 , R 47 and R 48 each independently represents an alkyl group having 1 to 8 carbon atoms, a phenyl group or a benzyl group,
The alkyl group represented by R 43 to R 48 is substituted or unsubstituted with a hydroxyl group, a halogen atom, a cyano group or a nitro group,
The phenyl group and benzyl group represented by R 43 to R 48 are substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group, or a vinyl group,
R 43 and R 44 , R 45 and R 46 , and R 47 and R 48 may be linked to form a 3- to 6-membered ring,
An q− represents a q-valent anion, q represents 1 or 2, p represents a coefficient for maintaining a neutral charge,
It has at least one substituent represented by the general formula (1) in the molecule. )
上記一般式(8)において、R31〜R42で表されるハロゲン原子、R31〜R42及びY11で表されるアルキル基、アリール基又はアリールアルキル基を置換してもよいハロゲン原子、R43〜R48で表されるアルキル基、フェニル基及びベンジル基を置換してもよいハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられる。
R31〜R48及びY11で表される炭素原子数1〜8のアルキル基並びにR43〜R48で表されるフェニル基及びベンジル基を置換してもよい炭素原子数1〜4のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示した基のうち、所定の炭素数を満たす基等が挙げられ、
R31〜R42及びY11で表される炭素原子数6〜12のアリール基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基として例示した基のうち、所定の炭素数を満たす基等が挙げられ、
R31〜R42及びY11で表される炭素原子数7〜20のアリールアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数7〜20のアリールアルキル基として例示した基等が挙げられ、
R32とR43、R33とR44、R36とR45、R37とR46、R40とR47、R41とR48、R31とR32、R33とR34、R35とR36、R37とR38、R39とR40及びR41とR42が連結して形成し得る6員環としては、ピペリジン環、ピリジン環、ピリミジン環、キノリン環、イソキノリン環、ジュロリジン環等が挙げられ、
R31とR42、R34とR35及びR38とR39は、単結合、酸素原子、硫黄原子、セレン原子、CR49R50、CO、NR51、PR52又はSO2を介して連結して形成し得る環としては、ジヒドロアントラセン環、アクリジン環、キサンテン環、チオキサンテン環等が挙げられ、
R43とR44、R45とR46、及びR47とR48が連結して形成し得る3〜6員環の複素環としては、ピペリジン環、ピペラジン環、ピロリジン環、モルフォリン環、チオモルフォリン環、ピリジン環、ピラジン環、ピリミジン環、キノリン環、イソキノリン環、イミダゾール環、オキサゾール環、イミダゾリジン環、ピラゾリジン環、イソオキサゾリジン環、イソチアゾリジン環等が挙げられ、これらの環は他の環と縮合されていたり、置換されていたりしていてもよい。In the general formula (8), a halogen atom represented by R 31 to R 42 , an alkyl group represented by R 31 to R 42 and Y 11 , an aryl group or a halogen atom that may be substituted with an arylalkyl group, Examples of the halogen atom that may be substituted for the alkyl group, phenyl group and benzyl group represented by R 43 to R 48 are the halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05. Group.
Alkyl group having 1 to 8 carbon atoms represented by R 31 to R 48 and Y 11 , and alkyl having 1 to 4 carbon atoms which may be substituted with phenyl group and benzyl group represented by R 43 to R 48 Examples of groups include R 01 , R 02 , R 03 , R 04 and R 05 and groups satisfying a predetermined carbon number among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 1. Named,
Examples of the aryl group having 6 to 12 carbon atoms represented by R 31 to R 42 and Y 11 include R 01 , R 02 , R 03 , R 04 and R 05 and 6 to 6 carbon atoms represented by R 1 . Among the groups exemplified as the 20 aryl group, a group satisfying a predetermined number of carbons and the like can be mentioned.
Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 31 to R 42 and Y 11 include 7 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1. Groups exemplified as ˜20 arylalkyl groups, and the like,
R 32 and R 43 , R 33 and R 44 , R 36 and R 45 , R 37 and R 46 , R 40 and R 47 , R 41 and R 48 , R 31 and R 32 , R 33 and R 34 , R 35 And R 36 , R 37 and R 38 , R 39 and R 40, and R 41 and R 42 may be linked to form a 6-membered ring such as a piperidine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, or a julolidine ring. Ring, etc.
R 31 and R 42 , R 34 and R 35 and R 38 and R 39 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 49 R 50 , CO, NR 51 , PR 52 or SO 2. Examples of the ring that can be formed include a dihydroanthracene ring, an acridine ring, a xanthene ring, and a thioxanthene ring.
Examples of the 3- to 6-membered heterocyclic ring that can be formed by linking R 43 and R 44 , R 45 and R 46 , and R 47 and R 48 include a piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiol Morpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, isothiazolidine ring, and the like. It may be condensed with a ring or may be substituted.
上記一般式(8)において、Anq-で表される陰イオンとしては、例えば、一価のものとして、塩化物イオン、臭化物イオン、ヨウ化物イオン、フッ化物イオン等のハロゲン化物イオン;過塩素酸イオン、塩素酸イオン、チオシアン酸イオン、ヘキサフルオロリン酸イオン、ヘキサフルオロアンチモン酸イオン、テトラフルオロホウ酸イオン等の無機系陰イオン;メタンスルホン酸イオン、ドデシルスルホン酸イオン、ベンゼンスルホン酸イオン、トルエンスルホン酸イオン、トリフルオロメタンスルホン酸イオン、ナフタレンスルホン酸イオン、ジフェニルアミン−4−スルホン酸イオン、2−アミノ−4−メチル−5−クロロベンゼンスルホン酸イオン、2−アミノ−5−ニトロベンゼンスルホン酸イオン、フタロシアニンスルホン酸イオン、重合性置換基を有するスルホン酸イオン、特開平10−235999、特開平10−337959、特開平11−102088、特開2000−108510、特開2000−168223、特開2001−209969、特開2001−322354、特開2006−248180、特開2006−297907、特開平8−253705号公報、特表2004−503379号公報、特開2005−336150号公報、国際公開2006/28006号公報等に記載されたスルホン酸イオン等の有機スルホン酸系陰イオン;オクチルリン酸イオン、ドデシルリン酸イオン、オクタデシルリン酸イオン、フェニルリン酸イオン、ノニルフェニルリン酸イオン、2,2’−メチレンビス(4,6−ジ−t−ブチルフェニル)ホスホン酸イオン等の有機リン酸系陰イオン、ビストリフルオロメチルスルホニルイミドイオン、ビスパーフルオロブタンスルホニルイミドイオン、パーフルオロ−4−エチルシクロヘキサンスルホン酸イオン、テトラキス(ペンタフルオロフェニル)ホウ酸イオン、トリス(フルオロアルキルスルホニル)カルボアニオン等が挙げられ、二価のものとしては、例えば、ベンゼンジスルホン酸イオン、ナフタレンジスルホン酸イオン等が挙げられる。また、励起状態にある活性分子を脱励起させる(クエンチングさせる)機能を有するクエンチャー陰イオンやシクロペンタジエニル環にカルボキシル基やホスホン酸基、スルホン酸基等の陰イオン性基を有するフェロセン、ルテオセン等のメタロセン化合物陰イオン等も、必要に応じて用いることができる。また、pは、分子全体で電荷が中性となるように選択される。In the above general formula (8), examples of the anion represented by An q- include monovalent ions such as chloride ions, bromide ions, iodide ions, fluoride ions, and the like; perchlorine Inorganic anions such as acid ion, chlorate ion, thiocyanate ion, hexafluorophosphate ion, hexafluoroantimonate ion, tetrafluoroborate ion; methanesulfonate ion, dodecylsulfonate ion, benzenesulfonate ion, Toluenesulfonic acid ion, trifluoromethanesulfonic acid ion, naphthalenesulfonic acid ion, diphenylamine-4-sulfonic acid ion, 2-amino-4-methyl-5-chlorobenzenesulfonic acid ion, 2-amino-5-nitrobenzenesulfonic acid ion, Phthalocyanine sulfonic acid Sulfonate ions having a polymerizable substituent, JP-A-10-235999, JP-A-10-337959, JP-A-11-102808, JP-A-2000-108510, JP-A-2000-168223, JP-A-2001-209969, JP 2001-322354, JP-A-2006-248180, JP-A-2006-297907, JP-A-8-253705, JP-T-2004-503379, JP-A-2005-336150, International Publication 2006/28006, etc. Organic sulfonate anions such as sulfonate ions; octyl phosphate ions, dodecyl phosphate ions, octadecyl phosphate ions, phenyl phosphate ions, nonylphenyl phosphate ions, 2,2′-methylenebis (4,6- Di-t-butylphenyl) phosphonic acid Organic phosphate anions such as ON, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4-ethylcyclohexanesulfonate ion, tetrakis (pentafluorophenyl) borate ion, tris (fluoroalkyl) Sulfonyl) carbanion and the like, and examples of the divalent include benzene disulfonate ion, naphthalenedisulfonate ion and the like. In addition, quencher anions that have the function of deexciting (quenching) active molecules in the excited state, and ferrocenes having an anionic group such as a carboxyl group, phosphonic acid group, or sulfonic acid group on the cyclopentadienyl ring. Metallocene compound anions such as luteocene can also be used as necessary. Also, p is selected so that the charge is neutral throughout the molecule.
上記一般式(8)においては、Anq-で表される陰イオンが、上記一般式(1)で表される置換基を1〜10個有していてもよく、このような陰イオンとしては、例えば、下記[化19A]で表される陰イオンが挙げられるが、本発明はこれらの陰イオンに制限されない。In the general formula (8), the anion represented by An q- may have 1 to 10 substituents represented by the general formula (1). Examples include anions represented by the following [Chemical 19A], but the present invention is not limited to these anions.
上記のクエンチャー陰イオンとしては、例えば、特開昭60−234892号公報、特開平5−43814号公報、特開平5−305770号公報、特開平6−239028号公報、特開平9−309886号公報、特開平9−323478号公報、特開平10−45767号公報、特開平11−208118号公報、特開2000−168237号公報、特開2002−201373号公報、特開2002−206061号公報、特開2005−297407号公報、特公平7−96334号公報、国際公開98/29257号公報等に記載されたような陰イオンが挙げられる。 Examples of the quencher anion include, for example, JP-A-60-234892, JP-A-5-43814, JP-A-5-305770, JP-A-6-239028, JP-A-9-309886. JP-A-9-323478, JP-A-10-45767, JP-A-11-208118, JP-A-2000-168237, JP-A-2002-201373, JP-A-2002-206061, Examples include anions as described in JP-A-2005-297407, JP-B-7-96334, WO98 / 29257, and the like.
上記一般式(I)中のAnq-で表される陰イオンとしては、一価の有機スルホン酸系陰イオン、ビストリフルオロメチルスルホニルイミドイオン、ビスパーフルオロブタンスルホニルイミドイオン、パーフルオロ−4−エチルシクロヘキサンスルホン酸イオン、ベンゼンジスルホン酸イオン、ナフタレンジスルホン酸イオンが耐熱性の点から好ましく、ビストリフルオロメチルスルホニルイミドイオンがさらに好ましい。Examples of the anion represented by An q- in the general formula (I) include a monovalent organic sulfonic acid anion, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, and perfluoro-4- Ethylcyclohexanesulfonate ion, benzenedisulfonate ion, and naphthalenedisulfonate ion are preferable from the viewpoint of heat resistance, and bistrifluoromethylsulfonylimide ion is more preferable.
上記一般式(8)で表される化合物の具体例としては、下記[化20A]及び[化20B]で表される化合物が挙げられるが、本発明はこれらの化合物に制限されない。 Specific examples of the compound represented by the general formula (8) include compounds represented by the following [Chemical 20A] and [Chemical 20B], but the present invention is not limited to these compounds.
上記シアニン化合物の中でも、合成の容易さ及び分子設計の点から、下記一般式(9)〜(12)の何れかで表されるものが好ましい。 Among the cyanine compounds, those represented by any one of the following general formulas (9) to (12) are preferable from the viewpoint of ease of synthesis and molecular design.
Qは炭素原子数1〜9のメチン鎖を構成し、鎖中に環構造を含んでもよい連結基を表し、該メチン鎖中の水素原子は水酸基、ハロゲン原子、シアノ基、−NR51R52、炭素原子数6〜12のアリール基、炭素原子数7〜12のアリールアルキル基又は炭素原子数1〜8のアルキル基で置換されていてもよく、該−NR51R52、アリール基、アリールアルキル基及びアルキル基は、更に水酸基、ハロゲン原子、シアノ基又は−NR51R52で置換されていてもよく、−NR51R52、アリール基、アリールアルキル基及びアルキル基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−SO2−、−NH−、−CONH−、−NHCO−、−N=CH−又は−CH=CH−で置き換わっていてもよく、
R51及びR52は、炭素原子数6〜12のアリール基、炭素原子数7〜12のアリールアルキル基又は炭素原子数1〜8のアルキル基を表し、
Anq-はq価のアニオンを表し、qは1又は2を表し、pは電荷を中性に保つ係数を表し、
分子内に上記一般式(1)で表される置換基を少なくとも一つ有する。)
Q represents a methine chain having 1 to 9 carbon atoms, and represents a linking group that may include a ring structure in the chain. The hydrogen atom in the methine chain is a hydroxyl group, a halogen atom, a cyano group, —NR 51 R 52. , An aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or an alkyl group having 1 to 8 carbon atoms, the —NR 51 R 52 , aryl group, aryl The alkyl group and the alkyl group may be further substituted with a hydroxyl group, a halogen atom, a cyano group or —NR 51 R 52. —NR 51 R 52 , an aryl group, an arylalkyl group and a methylene group in the alkyl group are -O -, - S -, - CO -, - COO -, - OCO -, - SO 2 -, - NH -, - CONH -, - NHCO -, - substituted N = CH- or -CH = CH- You may,
R 51 and R 52 represent an aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or an alkyl group having 1 to 8 carbon atoms,
An q− represents a q-valent anion, q represents 1 or 2, p represents a coefficient for maintaining a neutral charge,
It has at least one substituent represented by the general formula (1) in the molecule. )
R53及びR53’は、水酸基、ハロゲン原子、ニトロ基、シアノ基、−SO3H、カルボキシル基、アミノ基、アミド基、フェロセニル基、炭素原子数6〜30のアリール基、炭素原子数7〜30のアリールアルキル基又は炭素原子数1〜8のアルキル基を表し、
R53及びR53’で表されるアリール基、アリールアルキル基及びアルキル基は、水酸基、ハロゲン原子、ニトロ基、シアノ基、−SO3H、カルボキシル基、アミノ基、アミド基又はフェロセニル基で置換されていてもよく、
R53及びR53’で表されるアリール基、アリールアルキル基及びアルキル基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−SO2−、−NH−、−CONH−、−NHCO−、−N=CH−又は−CH=CH−で置き換わっていてもよく、 R54〜R61及びR54’〜R61’は、R53及びR53’と同様の基又は水素原子を表し、
X12、X12’、X13及びX13’は、酸素原子、硫黄原子、セレン原子、−CR62R63−、炭素原子数3〜6のシクロアルカン−1,1−ジイル基、−NH−又は−NY13−を表し、
R62及びR63は、R53及びR53’と同様の基又は水素原子を表し、
Y12、Y12’及びY13は、炭素原子数1〜20のアルキル基、炭素原子数6〜30のアリール基又は炭素原子数7〜30のアリールアルキル基を表し、
Y12、Y12’及びY13で表されるアルキル基、アリール基及びアリールアルキル基は、水酸基、ハロゲン原子、シアノ基、カルボキシル基、アミノ基、アミド基、フェロセニル基、−SO3H若しくはニトロ基で置換されているか又は無置換であり、
Y12、Y12’及びY13で表されるアルキル基、アリール基及びアリールアルキル基中のメチレン基は、−O−、−S−、−CO−、−COO−、−OCO−、−SO2−、−NH−、−CONH−、−NHCO−、−N=CH−又は−CH=CH−で置き換わっていてもよく、
r及びr’は、0又は(a)〜(e)、(g)〜(j)、(l)、(m)、(a’)〜(e’)、(g’)〜(j’)、(l’)及び(m’)において置換可能な数を表す。)
R 53 and R 53 ′ are a hydroxyl group, a halogen atom, a nitro group, a cyano group, —SO 3 H, a carboxyl group, an amino group, an amide group, a ferrocenyl group, an aryl group having 6 to 30 carbon atoms, or a carbon atom number of 7 Represents an arylalkyl group of ˜30 or an alkyl group of 1 to 8 carbon atoms,
The aryl group, arylalkyl group and alkyl group represented by R 53 and R 53 ′ are substituted with a hydroxyl group, a halogen atom, a nitro group, a cyano group, —SO 3 H, a carboxyl group, an amino group, an amide group or a ferrocenyl group. May have been
The aryl group represented by R 53 and R 53 ′, the arylalkyl group and the methylene group in the alkyl group are —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, -NH -, - CONH -, - NHCO -, - N = CH- or may be replaced by -CH = CH-, R 54 ~R 61 and R 54 '~R 61' is, R 53 and R 53 Represents the same group or hydrogen atom as
X 12 , X 12 ′, X 13 and X 13 ′ are an oxygen atom, a sulfur atom, a selenium atom, —CR 62 R 63 —, a C 3-6 cycloalkane-1,1-diyl group, —NH - or -NY 13 - represents,
R 62 and R 63 represent the same group or hydrogen atom as R 53 and R 53 ′,
Y 12 , Y 12 ′ and Y 13 each represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an arylalkyl group having 7 to 30 carbon atoms,
The alkyl group, aryl group and arylalkyl group represented by Y 12 , Y 12 ′ and Y 13 are a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, an amino group, an amide group, a ferrocenyl group, —SO 3 H or nitro. Substituted or unsubstituted with a group,
The alkyl group represented by Y 12 , Y 12 ′ and Y 13 , the aryl group and the methylene group in the arylalkyl group are —O—, —S—, —CO—, —COO—, —OCO—, —SO. 2 —, —NH—, —CONH—, —NHCO—, —N═CH— or —CH═CH— may be substituted,
r and r ′ are 0 or (a) to (e), (g) to (j), (l), (m), (a ′) to (e ′), (g ′) to (j ′) ), (L ′) and (m ′) represent the number that can be substituted. )
上記一般式(9)において、Qは炭素原子数1〜9のメチン鎖を構成し、鎖中に環構造を含んでもよい連結基としては、下記(Q−1)〜(Q−11)の何れかで表される基が、製造が容易であるため好ましい。炭素原子数1〜9のメチン鎖における炭素原子数には、メチン鎖及び鎖中に環構造を含んでもよい連結基を表し、該連結基をさらに置換する基(例えば下記R62〜R67、Z’)の炭素原子(例えば、連結基(Q−1)における両末端の炭素原子)を含まない。In the above general formula (9), Q constitutes a methine chain having 1 to 9 carbon atoms, and the linking group that may contain a ring structure in the chain includes the following (Q-1) to (Q-11): A group represented by any one is preferable because it is easy to produce. The number of carbon atoms in the methine chain having 1 to 9 carbon atoms represents a methine chain and a linking group that may include a ring structure in the chain, and a group that further substitutes the linking group (for example, R 62 to R 67 below, Z ′) carbon atoms (for example, carbon atoms at both ends in the linking group (Q-1)) are not included.
R62〜R67及びZ’で表される−NRR’、アリール基、アリールアルキル基及びアルキル基は、水酸基、ハロゲン原子、シアノ基又は−NRR’で置換されていてもよく、−O−、−S−、−CO−、−COO−、−OCO−、−SO2−、−NH−、−CONH−、−NHCO−、−N=CH−又は−CH=CH−で中断されていてもよく、
R及びR’は、炭素原子数6〜12のアリール基、炭素原子数7〜12のアリールアルキル基又は炭素原子数1〜8のアルキルを表す。)
—NRR ′, aryl group, arylalkyl group and alkyl group represented by R 62 to R 67 and Z ′ may be substituted with a hydroxyl group, a halogen atom, a cyano group or —NRR ′, and —O—, Even if interrupted by —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N═CH— or —CH═CH—. Often,
R and R ′ represent an aryl group having 6 to 12 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or alkyl having 1 to 8 carbon atoms. )
上記のR62〜R67及びZ’で表わされるハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられる。
上記のR62〜R67、Z’、R及びR’で表される炭素原子数6〜12のアリール基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基として例示した基のうち、所定の炭素数を満たす基等が挙げられ、
上記のR62〜R67、Z’、R及びR’で表される炭素原子数7〜12のアリールアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数6〜20のアリール基として例示した基のうち、所定の炭素数を満たす基等が挙げられる。
上記一般式(9)において、Anq-で表される陰イオンとしては、上記一般式(8)におけるAnq-で表される陰イオンとして例示した基等が挙げられる。Examples of the halogen atom represented by R 62 to R 67 and Z ′ include groups exemplified as the halogen atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 .
The aryl group having 6 to 12 carbon atoms represented by R 62 to R 67 , Z ′, R and R ′ is represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . Among the groups exemplified as the aryl group having 6 to 20 carbon atoms, a group satisfying a predetermined carbon number, and the like can be mentioned.
Examples of the arylalkyl group having 7 to 12 carbon atoms represented by R 62 to R 67 , Z ′, R, and R ′ include R 01 , R 02 , R 03 , R 04, R 05 , and R 1 . Of the groups exemplified as the aryl group having 6 to 20 carbon atoms, groups that satisfy a predetermined number of carbons can be given.
In the general formula (9), An as the anion represented by q-, etc. exemplified groups as an anion represented by An q- in the general formula (8) below.
上記一般式(10)における2つのD並びに上記一般式(11)、(12)におけるD及びD’としては、化合物として電荷が中性となるように、ノニオン性基一つとカチオン性基を一つ選択する。
上記一般式(10)〜(12)におけるR53〜R63及びR53’〜R63’で表されるハロゲン原子、R53及びR53’で表されるアリール基、アリールアルキル基及びアルキル基を置換してもよいハロゲン原子、並びにY12、Y12’及びY13で表されるアルキル基、アリール基及びアリールアルキル基を置換してもよいハロゲン原子としては、R01、R02、R03、R04及びR05で表されるハロゲン原子として例示した基が挙げられる。
R53〜R63及びR53’〜R63’並びにY12、Y12’及びY13で表される炭素原子数6〜30のアリール基としては、フェニル、ナフチル、2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、4−ビニルフェニル、3−iso−プロピルフェニル、4−iso−プロピルフェニル、4−ブチルフェニル、4−iso−ブチルフェニル、4−tert−ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、4−ステアリルフェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ−tert−ブチルフェニル、2,5−ジ−tert−ブチルフェニル、2,6−ジ−tert−ブチルフェニル、2,4−ジ−tert−ペンチルフェニル、2,5−ジ−tert−アミルフェニル、2,5−ジ−tert−オクチルフェニル、2,4−ジクミルフェニル、4−シクロヘキシルフェニル、(1,1’−ビフェニル)−4−イル、2,4,5−トリメチルフェニル、フェロセニル等が挙げられ、
R53〜R63及びR53’〜R63’並びにY12、Y12’及びY13で表される炭素原子数7〜30のアリールアルキル基としては、ベンジル、フェネチル、2−フェニルプロパン−2−イル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル、フェロセニルメチル、フェロセニルプロピル等が挙げられ、
R53〜R63及びR53’〜R63’で表される炭素原子数1〜8のアルキル基、並びにY12、Y12’及びY13で表される炭素原子数1〜20のアルキル基としては、R01、R02、R03、R04及びR05並びにR1で表される炭素原子数1〜40のアルキル基として例示した基のうち、所定の炭素数を満たす基等が挙げられる。Two Ds in the general formula (10) and D and D ′ in the general formulas (11) and (12) are one nonionic group and one cationic group so that the charge becomes neutral as a compound. Select one.
R 53 to R 63 and R 53 ′ to R 63 ′ in the above general formulas (10) to (12), a halogen atom represented by R 53 and R 53 ′, an aryl group, an arylalkyl group and an alkyl group As the halogen atom that may be substituted, and the halogen atom that may be substituted for the alkyl group, aryl group, and arylalkyl group represented by Y 12 , Y 12 ′, and Y 13 , R 01 , R 02 , R The group illustrated as a halogen atom represented by 03 , R04, and R05 is mentioned.
Examples of the aryl group having 6 to 30 carbon atoms represented by R 53 to R 63 and R 53 ′ to R 63 ′ and Y 12 , Y 12 ′ and Y 13 include phenyl, naphthyl, 2-methylphenyl, 3- Methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6- Dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di- tert-octylphenyl, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1′-biphenyl) -4-yl, 2,4,5-trimethylphenyl, ferrocenyl, etc.
Examples of the arylalkyl group having 7 to 30 carbon atoms represented by R 53 to R 63 and R 53 ′ to R 63 ′ and Y 12 , Y 12 ′ and Y 13 include benzyl, phenethyl, 2-phenylpropane-2 -Yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, ferrocenylmethyl, ferrocenylpropyl and the like,
An alkyl group having 1 to 8 carbon atoms represented by R 53 to R 63 and R 53 ′ to R 63 ′, and an alkyl group having 1 to 20 carbon atoms represented by Y 12 , Y 12 ′ and Y 13 As R 01 , R 02 , R 03 , R 04 and R 05 and groups exemplified as alkyl groups having 1 to 40 carbon atoms represented by R 1 , groups satisfying a predetermined carbon number, etc. It is done.
上記一般式(10)〜(12)において、X12、X12’、X13及びX13’で表される炭素原子数3〜6のシクロアルカン−1,1−ジイル基としては、シクロプロパン−1,1−ジイル、シクロブタン−1,1−ジイル、2,4−ジメチルシクロブタン−1,1−ジイル、3,3−ジメチルシクロブタン−1,1−ジイル、シクロペンタン−1,1−ジイル、シクロヘキサン−1,1−ジイル等が挙げられる。In the general formulas (10) to (12), the cycloalkane-1,1-diyl group having 3 to 6 carbon atoms represented by X 12 , X 12 ′, X 13 and X 13 ′ is cyclopropane. -1,1-diyl, cyclobutane-1,1-diyl, 2,4-dimethylcyclobutane-1,1-diyl, 3,3-dimethylcyclobutane-1,1-diyl, cyclopentane-1,1-diyl, And cyclohexane-1,1-diyl.
上記一般式(9)〜(12)で表される化合物の具体例としては、下記[化24]で表される化合物が挙げられるが、本発明はこれらの化合物に制限されない。 Specific examples of the compounds represented by the general formulas (9) to (12) include compounds represented by the following [Chemical Formula 24], but the present invention is not limited to these compounds.
本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物の製造方法は特に限定されないが、例えば、紫外から近赤外の波長領域に吸収極大を有する有機色素として、シアノスチレン化合物、トリアリールメタン化合物、シアニン化合物を公知の方法により製造した後、これに、酸塩化物、Boc化試薬、アルキルハライド化合物、シリルクロライド化合物、アリルエーテル化合物等を反応させて、上記一般式(1)で表される構造を導入することにより得る方法を挙げることができる。 There is no particular limitation on the method for producing the compound of the present invention, which is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region and having at least one structure represented by the general formula (1) in the molecule. For example, a cyanostyrene compound, a triarylmethane compound, and a cyanine compound are produced by a known method as an organic dye having an absorption maximum in a wavelength region from ultraviolet to near infrared, and then, an acid chloride and a Boc reagent are added thereto. , Alkyl halide compounds, silyl chloride compounds, allyl ether compounds, and the like, and a method obtained by introducing the structure represented by the general formula (1).
本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物は、染料として以下に説明する着色感光性組成物に用いられる他、ディスプレイや光学レンズに用いられる光学フィルタ、銀塩写真用感光材料、染物、塗料、インク、電子写真感光体、トナー、感熱記録紙、転写リボン、光学記録色素、太陽電池、有機半導体、臨床検査試薬、レーザー治療用色素、染色等に用いられる。
また、酸化防止剤として光硬化性組成物、熱硬化性組成物又は重合性組成物に用いられる他、顕色剤として感熱材料にも用いられる。The organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention and having at least one structure represented by the general formula (1) in the molecule will be described below as a dye. In addition to colored photosensitive compositions, optical filters used in displays and optical lenses, silver halide photographic photosensitive materials, dyed articles, paints, inks, electrophotographic photoreceptors, toners, thermal recording paper, transfer ribbons, optical recording dyes , Solar cells, organic semiconductors, clinical laboratory reagents, laser therapeutic dyes, dyeing, etc.
In addition to being used as a photocurable composition, a thermosetting composition or a polymerizable composition as an antioxidant, it is also used as a color developer in a heat-sensitive material.
本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に下記一般式(1)で表される構造を少なくとも一つ有する化合物は、上記一般式(1)において、R1が水素原子でない場合、潜在性添加剤として用いることもできる。
潜在性添加剤とは、常温或いは150℃以下のプリベーク工程では不活性であり、100〜250℃で加熱するか、又は酸/塩基触媒存在下で80〜200℃で加熱することにより保護基が脱離して活性となるものであり、具体的には、潜在性酸化防止剤、潜在性紫外線吸収剤等の潜在性樹脂添加剤;感熱紙用潜在性顕色剤;感熱紙用潜在性保存安定剤;潜在性硬化剤等が挙げられる。The organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention and having at least one structure represented by the following general formula (1) in the molecule is the above general formula (1). When R 1 is not a hydrogen atom, it can also be used as a latent additive.
The latent additive is inactive in a pre-baking step at room temperature or 150 ° C., and the protective group is formed by heating at 100 to 250 ° C. or heating at 80 to 200 ° C. in the presence of an acid / base catalyst. Detachable and active, specifically, latent resin additives such as latent antioxidants and latent UV absorbers; latent developer for thermal paper; latent storage stability for thermal paper Agents; latent curing agents and the like.
続いて、本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物を含有する組成物について説明する。
本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物を含有する組成物は、着色感光性組成物として用いられる他、重合性組成物としても用いられる。
上記着色感光性組成物として用いる場合、本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物の含有量は、0.01〜50質量%が好ましく、0.1〜30質量%がより好ましい。Subsequently, the organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention, comprising a compound having at least one structure represented by the general formula (1) in the molecule Will be described.
The composition containing an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention and having at least one structure represented by the general formula (1) in the molecule is colored. In addition to being used as a photosensitive composition, it is also used as a polymerizable composition.
When used as the colored photosensitive composition, it is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region of the present invention, and has at least one structure represented by the general formula (1) in the molecule 0.01-50 mass% is preferable and, as for content of the compound which has, 0.1-30 mass% is more preferable.
上記着色感光性組成物は、光照射によって硬化するものであり、光カチオン硬化性、光アニオン硬化性或いは光ラジカル硬化性の何れでもよいが、光ラジカル硬化性であるものが好ましい。
上記着色感光性組成物が、光ラジカル硬化性である場合、着色感光性組成物は、本発明の紫外から近赤外の波長領域に吸収極大を有する有機色素であって、分子内に上記一般式(1)で表される構造を少なくとも一つ有する化合物の他、酸価を有するエチレン性不飽和結合を有する重合性化合物及び光ラジカル重合開始剤を必須成分とする。以下、この着色感光性組成物を、本発明の着色感光性組成物ともいう。The colored photosensitive composition is cured by light irradiation, and may be any of photocation curable, photoanion curable, or photo radical curable, but is preferably a photo radical curable.
When the colored photosensitive composition is photo-radical curable, the colored photosensitive composition is an organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region according to the present invention, In addition to the compound having at least one structure represented by the formula (1), a polymerizable compound having an ethylenically unsaturated bond having an acid value and a radical photopolymerization initiator are essential components. Hereinafter, this colored photosensitive composition is also referred to as a colored photosensitive composition of the present invention.
上記酸価を有するエチレン性不飽和結合を有する重合性化合物としては、 (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;フェノール及び/又はクレゾールノボラックエポキシ樹脂、ビフェニル骨格、ナフタレン骨格を有するノボラックエポキシ樹脂、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物、多官能エポキシ基を有するポリフェニルメタン型エポキシ樹脂、下記一般式(13)で表されるエポキシ化合物等のエポキシ樹脂のエポキシ基に不飽和一塩基酸を作用させ、更に多塩基酸無水物を作用させて得られた樹脂、ペンタエリスリトールトリアクリレート、ジペンタエリスリトールペンタアクリレート等の水酸基含有多官能アクリレートと無水コハク酸、無水フタル酸、テトラヒドロ無水フタル酸等の二塩基酸無水物の反応物である酸価を有する多官能アクリレート等の重合体が挙げられる。 Examples of the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, and isocrotonic acid. , Vinyl acetate, allyl acetate, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ω-carboxypoly Mono (meth) acrylate, hydroxyethyl (meth) acrylate / malate, hydroxypropyl (meth) acrylate / malate, dicyclopentadiene / malate, which has a carboxy group and a hydroxyl group at both ends, such as caprolactone mono (meth) acrylate 1 carboxyl group and 2 or more (meth) acrylo Unsaturated polybasic acid such as polyfunctional (meth) acrylate having an yl group; phenol and / or cresol novolac epoxy resin, biphenyl skeleton, novolak epoxy resin having naphthalene skeleton, bisphenol A novolac type epoxy compound, dicyclopentadiene novolak An unsaturated monobasic acid acts on an epoxy group of an epoxy resin such as a novolak type epoxy compound such as an epoxy compound, a polyphenylmethane type epoxy resin having a polyfunctional epoxy group, and an epoxy compound represented by the following general formula (13) Resin obtained by further reacting with polybasic acid anhydride, polyfunctional acrylate containing hydroxyl group such as pentaerythritol triacrylate, dipentaerythritol pentaacrylate, succinic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, etc. Polymers such as polyfunctional acrylate having an acid value which is a reaction product of a dibasic acid anhydride.
これらの重合性化合物は、単独で又は2種以上を混合して使用することができ、また、酸価を有しないエチレン性不飽和結合を有する重合性化合物と組み合わせて使用することができる。2種以上を混合して使用する場合には、それらを予め共重合して共重合体として使用してもよい。 These polymerizable compounds can be used alone or in admixture of two or more, and can be used in combination with a polymerizable compound having an ethylenically unsaturated bond having no acid value. When two or more kinds are mixed and used, they may be copolymerized in advance and used as a copolymer.
上記酸価を有しないエチレン性不飽和結合を有する重合性化合物としては、例えば、(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、下記化合物No.A1〜No.A4、(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ペンタ(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、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;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;(メタ)アクリロニトリル、エチレン、プロピレン、ブチレン、塩化ビニル、酢酸ビニル等のその他のビニル化合物、及びポリメチルメタクリレートマクロモノマー、ポリスチレンマクロモノマー等のマクロモノマー類、トリシクロデカン骨格のモノメタクリレート、N−フェニルマレイミド、メタクリロイルオキシメチル−3−エチルオキセタン等と、(メタ)アクリル酸との共重合体及びこれらに昭和電工(株)社製カレンズMOI、AOIのような不飽和結合を有するイソシアネート化合物を反応させた(メタ)アクリル酸の共重合体や、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、ペンタエリスリトールトリアクリレート、ジペンタエリスリトールペンタアクリレート等の水酸基含有多官能アクリレートと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等の多官能イソシアネートの反応物等が挙げられる。 Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include (meth) acrylic acid-2-hydroxyethyl, (meth) acrylic acid-2-hydroxypropyl, (meth) acrylic acid glycidyl, The following compound No. A1-No. A4, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, (meta ) Ethylhexyl acrylate, (meth) acrylic acid Enoxyethyl, 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, trimethylolethanetri ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol Unsaturated monobasic acids such as tra (meth) acrylate, pentaerythritol tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, tri [(meth) acryloylethyl] isocyanurate, polyester (meth) acrylate oligomers and the like Esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyl Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydro Phthalic anhydride-anhydrous Acid anhydrides of unsaturated polybasic acids such as rain acid adducts, dodecenyl succinic anhydride, methyl hymic anhydride; (meth) acrylamide, methylene bis- (meth) acrylamide, diethylenetriamine tris (meth) acrylamide, xylylene bis (meth) Unsaturated monobasic acids such as acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; unsaturated aldehydes such as acrolein; (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, vinyl toluene, vinyl benzoic acid, vinyl Unsaturated aromatic compounds such as ruphenol, vinyl sulfonic acid, 4-vinylbenzene sulfonic acid, vinyl benzyl methyl ether, vinyl benzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinyl amine, allyl amine, N-vinyl pyrrolidone, vinyl Unsaturated amine compounds such as piperidine; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, allyl glycidyl ether; unsaturated imides such as maleimide, N-phenylmaleimide, N-cyclohexylmaleimide; indene Indene such as 1-methylindene; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene, chloroprene; polystyrene, polymethyl (meth) acrylate, poly-n- Macromonomers having a mono (meth) acryloyl group at the end of the polymer molecular chain such as til (meth) acrylate and polysiloxane; (meth) acrylonitrile, ethylene, propylene, butylene, vinyl chloride, vinyl acetate and other vinyls (Meth) acrylic acid, a compound, a macromonomer such as a polymethyl methacrylate macromonomer and a polystyrene macromonomer, monomethacrylate having a tricyclodecane skeleton, N-phenylmaleimide, methacryloyloxymethyl-3-ethyloxetane, and the like. Polymers and copolymers of (meth) acrylic acid in which an isocyanate compound having an unsaturated bond such as Karenz MOI and AOI manufactured by Showa Denko Co., Ltd. is reacted, vinyl chloride, vinylidene chloride, divinyl succin Naruto, Allyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomers and polyisocyanate vinyl urethane compounds, hydroxyl group-containing vinyl monomers And a reaction product of a polyfunctional isocyanate such as tolylene diisocyanate and hexamethylene diisocyanate with a hydroxyl group-containing polyfunctional acrylate such as a vinyl epoxy compound of a polyepoxy compound, pentaerythritol triacrylate, and dipentaerythritol pentaacrylate.
酸価調整して本発明の着色感光性組成物の現像性を改良するため、上記酸価を有するエチレン性不飽和結合を有する重合性化合物と共に、更に単官能又は多官能エポキシ化合物を用いることができる。上記酸価を有するエチレン性不飽和結合を有する重合性化合物は、固形分の酸価が5〜120mgKOH/gの範囲であることが好ましく、単官能又は多官能エポキシ化合物の使用量は、上記酸価を満たすように選択するのが好ましい。 In order to improve the developability of the colored photosensitive composition of the present invention by adjusting the acid value, a monofunctional or polyfunctional epoxy compound may be used together with the polymerizable compound having an ethylenically unsaturated bond having the acid value. it can. The polymerizable compound having an ethylenically unsaturated bond having the above acid value preferably has a solid content acid value in the range of 5 to 120 mgKOH / g, and the amount of the monofunctional or polyfunctional epoxy compound used is the above acid. It is preferable to select so as to satisfy the value.
上記単官能エポキシ化合物としては、グリシジルメタクリレート、メチルグリシジルエーテル、エチルグリシジルエーテル、プロピルグリシジルエーテル、イソプロピルグリシジルエーテル、ブチルグリシジルエーテル、イソブチルグリシジルエーテル、t−ブチルグリシジルエーテル、ペンチルグリシジルエーテル、ヘキシルグリシジルエーテル、ヘプチルグリシジルエーテル、オクチルグリシジルエーテル、ノニルグリシジルエーテル、デシルグリシジルエーテル、ウンデシルグリシジルエーテル、ドデシルグリシジルエーテル、トリデシルグリシジルエーテル、テトラデシルグリシジルエーテル、ペンタデシルグリシジルエーテル、ヘキサデシルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、アリルグリシジルエーテル、プロパルギルグリシジルエーテル、p−メトキシエチルグリシジルエーテル、フェニルグリシジルエーテル、p−メトキシグリシジルエーテル、p−ブチルフェノールグリシジルエーテル、クレジルグリシジルエーテル、2−メチルクレジルグリシジルエーテル、4−ノニルフェニルグリシジルエーテル、ベンジルグリシジルエーテル、p−クミルフェニルグリシジルエーテル、トリチルグリシジルエーテル、2,3−エポキシプロピルメタクリレート、エポキシ化大豆油、エポキシ化アマニ油、グリシジルブチレート、ビニルシクロヘキサンモノオキシド、1,2−エポキシ−4−ビニルシクロヘキサン、スチレンオキシド、ピネンオキシド、メチルスチレンオキシド、シクロヘキセンオキシド、プロピレンオキシド、等が挙げられる。 Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl. Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, Allyl glycidylate , Propargyl glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxy glycidyl ether, p-butylphenol glycidyl ether, cresyl glycidyl ether, 2-methyl cresyl glycidyl ether, 4-nonylphenyl glycidyl ether, benzyl glycidyl Ether, p-cumylphenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylate, epoxidized soybean oil, epoxidized linseed oil, glycidyl butyrate, vinylcyclohexane monooxide, 1,2-epoxy-4-vinyl Examples include cyclohexane, styrene oxide, pinene oxide, methyl styrene oxide, cyclohexene oxide, and propylene oxide.
上記多官能エポキシ化合物としては、ビスフェノール型エポキシ化合物及びグリシジルエーテル類からなる群から選択される一種以上を用いると、特性の一層良好な着色感光性組成物を得ることができるので好ましい。該ビスフェノール型エポキシ化合物としては、上記一般式(13)で表されるエポキシ化合物を用いることができる他、例えば、水添ビスフェノール型エポキシ化合物等のビスフェノール型エポキシ化合物も用いることができる。該グリシジルエーテル類としては、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、1,8−オクタンジオールジグリシジルエーテル、1,10−デカンジオールジグリシジルエーテル、2,2−ジメチル−1,3−プロパンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、テトラエチレングリコールジグリシジルエーテル、ヘキサエチレングリコールジグリシジルエーテル、1,4−シクロヘキサンジメタノールジグリシジルエーテル、1,1,1−トリ(グリシジルオキシメチル)プロパン、1,1,1−トリ(グリシジルオキシメチル)エタン、1,1,1−トリ(グリシジルオキシメチル)メタン、1,1,1,1−テトラ(グリシジルオキシメチル)メタンが挙げられる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4−エポキシ−6−メチルシクロヘキシルメチル−3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、1−エポキシエチル−3,4−エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジル−p−アミノフェノール、N,N−ジグリシジルアニリン等のグリシジルアミン類;1,3−ジグリシジル−5,5−ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物、トリフェニルメタン型エポキシ化合物、ジシクロペンタジエン型エポキシ化合物等を用いることもできる。As the polyfunctional epoxy compound, it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a colored photosensitive composition with better characteristics can be obtained. As the bisphenol type epoxy compound, an epoxy compound represented by the general formula (13) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used. Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (glycidyloxymethyl) methane, 1,1,1,1- tetra (glycidyloxymethyl) include methane.
Other novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxies such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin and triglycidyl isocyanurate; Dioxide compounds such as cyclopentadiene dioxide; naphthalene type epoxy compounds, triphenylmethane type epoxy compounds, dicyclopentadiene type epoxy compounds and the like can also be used.
本発明の着色感光性組成物において、上記酸価を有するエチレン性不飽和結合を有する重合性化合物の含有量は、本発明の着色感光性組成物中、1〜95質量%、特に10〜80質量%が好ましい。
また、上記酸価を有しないエチレン性不飽和結合を有する重合性化合物を使用する場合、その含有量は、上記酸価を有するエチレン性不飽和結合を有する重合性化合物100質量部に対して、10〜1000質量部とするのが好ましい。In the colored photosensitive composition of the present invention, the content of the polymerizable compound having an ethylenically unsaturated bond having an acid value is 1 to 95% by mass, particularly 10 to 80%, in the colored photosensitive composition of the present invention. Mass% is preferred.
Moreover, when using the polymeric compound which has the ethylenically unsaturated bond which does not have the said acid value, the content is with respect to 100 mass parts of polymeric compounds which have the ethylenically unsaturated bond which has the said acid value, It is preferable to set it as 10-1000 mass parts.
上記光ラジカル重合開始剤は、光照射を受けることによってラジカル重合を開始させることが可能となる化合物であればよく、例えば、アセトフェノン系化合物、ベンジル系化合物、ベンゾフェノン系化合物、オキシム系化合物、チオキサントン系化合物等のケトン系化合物等を好ましいものとして例示することができる。 The photo radical polymerization initiator may be any compound that can initiate radical polymerization upon receiving light irradiation, such as acetophenone compounds, benzyl compounds, benzophenone compounds, oxime compounds, thioxanthone compounds, for example. Examples of preferable compounds include ketone compounds such as compounds.
上記アセトフェノン系化合物としては例えば、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4'−イソプロピル−2−ヒドロキシ−2−メチルプロピオフェノン、2−ヒドロキシメチル−2−メチルプロピオフェノン、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、p−ジメチルアミノアセトフェノン、p−ターシャリブチルジクロロアセトフェノン、p−ターシャリブチルトリクロロアセトフェノン、p−アジドベンザルアセトフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパノン−1、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾイン−n−ブチルエーテル、ベンゾインイソブチルエーテル、1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン等が挙げられる。 Examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl- 2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azidoben Salacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) ) -Butanone-1, benzo In, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propane -1-one etc. are mentioned.
上記ベンジル系化合物としては、ベンジル、アニシル等が挙げられる。 Examples of the benzyl compound include benzyl and anisyl.
上記ベンゾフェノン系化合物としては、例えば、ベンゾフェノン、o−ベンゾイル安息香酸メチル、ミヒラーケトン、4,4'−ビスジエチルアミノベンゾフェノン、4,4'−ジクロロベンゾフェノン、4−ベンゾイル−4'−メチルジフェニルスルフィド等が挙げられる。 Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like. It is done.
上記オキシム系化合物としては、1.2−オクタンジオン,1−[4−(フェニルチオ)−,2−(O−ベンゾイルオキシム)]、エタノン,1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]−,1−(O−アセチルオキシム)、メタノン,(2−メチルフェニル)[6−ニトロ−9−[3−(トリメチルシリル)プロピル]−9H−カルバゾール−3−イル]−,1−O−アセチルオキシム)、メタノン,(9−エチル−6−ニトロ−9H−カルバゾール−3−イル)(2−メチルフェニル),O−アセチルオキシム、メタノン,(9−エチル−6−ニトロ−9H−カルバゾール−3−イル)[2−メチル−4−(4−モルホリニル)フェニル),O−アセチルオキシム、メタノン,(3,5−ジニトロフェニル)(9−エチル−6−ニトロ−9H−カルバゾール−3−イル)(2−メチルフェニル),O−アセチルオキシム、メタノン,(9−エチル−6−ニトロ−9H−カルバゾール−3−イル)(3−ニトロフェニル),O−アセチルオキシム、1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、1,3,5−トリス[2−(アセチルオキシ)−3−[3−[(1E)−1−[(アセチルオキシ)イミノエチル]−6−ニトロ−9H−カルバゾール−9−イル]プロピル]−、1,2−ブタンジオン、1−[4−(フェニルチオ)フェニル]−、2−(O−アセチルオキシム)、1,2−ブタンジオン、1−[4−[[4−(2−ヒドロキシエトキシ)フェニル]チオ]フェニル]−、2−(O−アセチルオキシム)、1,2−ブタンジオン、1,1’−(チオジ−4,1−フェニレン)ビス−、2,2−ビス(O−アセチルオキシム)、1,2−オクタンジオン、1−[4−(フェニルチオ)フェニル]−、2−[O−(4−メチルベンゾイル)オキシム]等が挙げられる。 Examples of the oxime compounds include 1.2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2-methylbenzoyl). ) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), methanone, (2-methylphenyl) [6-nitro-9- [3- (trimethylsilyl) propyl] -9H-carbazole-3 -Yl]-, 1-O-acetyloxime), methanone, (9-ethyl-6-nitro-9H-carbazol-3-yl) (2-methylphenyl), O-acetyloxime, methanone, (9-ethyl) -6-nitro-9H-carbazol-3-yl) [2-methyl-4- (4-morpholinyl) phenyl), O-acetyloxime, methanone, (3,5-dinitroph Nyl) (9-ethyl-6-nitro-9H-carbazol-3-yl) (2-methylphenyl), O-acetyloxime, methanone, (9-ethyl-6-nitro-9H-carbazol-3-yl) (3-nitrophenyl), O-acetyloxime, 1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, 1,3,5-tris [2- (acetyloxy)- 3- [3-[(1E) -1-[(acetyloxy) iminoethyl] -6-nitro-9H-carbazol-9-yl] propyl]-, 1,2-butanedione, 1- [4- (phenylthio) Phenyl]-, 2- (O-acetyloxime), 1,2-butanedione, 1- [4-[[4- (2-hydroxyethoxy) phenyl] thio] phenyl]-, 2- (O-acetyloxime) 1,2-butanedio 1,1 ′-(thiodi-4,1-phenylene) bis-, 2,2-bis (O-acetyloxime), 1,2-octanedione, 1- [4- (phenylthio) phenyl] -2, -[O- (4-methylbenzoyl) oxime] and the like.
上記チオキサントン系化合物としては、チオキサントン、2−メチルチオキサントン、2−エチルチオキサントン、2−クロロチオキサントン、2−イソプロピルチオキサントン、2,4−ジエチルチオキサントン等が挙げられる。 Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
その他の光ラジカル重合開始剤としては、2,4,6−トリメチルベンゾイルジフェニルフォスフェインオキサイド、ビス(シクロペンタジエニル)−ビス[2,6−ジフルオロ−3−(ピル−1−イル)]チタニウム等が挙げられる。 Other radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1-yl)] titanium. Etc.
これらの光ラジカル重合開始剤は1種或いは2種以上のものを所望の性能に応じて配合して使用することができる。 These radical photopolymerization initiators can be used alone or in combination according to the desired performance.
以上のような光ラジカル重合開始剤は、ラジカル重合性有機物質(上記酸価を有するエチレン性不飽和結合を有する重合性化合物、酸価を有しないエチレン性不飽和結合を有する重合性化合物、単官能又は多官能エポキシ化合物)に対して化学量論的必要量を使用すればよいが、好ましくはラジカル重合性有機物質に対して0.05〜10質量部、更に好ましくは0.1〜10質量部配合するのがよい。この範囲を上回ると十分な強度を有する硬化物が得られない場合があり、下回ると樹脂が十分硬化しない場合がある。 The radical photopolymerization initiator as described above is a radical polymerizable organic substance (polymerizable compound having an ethylenically unsaturated bond having an acid value, polymerizable compound having an ethylenically unsaturated bond having no acid value, a single compound, The stoichiometrically required amount may be used for the functional or polyfunctional epoxy compound), preferably 0.05 to 10 parts by weight, more preferably 0.1 to 10 parts by weight with respect to the radical polymerizable organic substance. It is better to mix part. If this range is exceeded, a cured product having sufficient strength may not be obtained, and if it is less than this range, the resin may not be sufficiently cured.
本発明の着色感光性組成物において、上記光ラジカル重合開始剤の含有量は、本発明の着色感光性組成物中、0.1〜30質量%、特に0.5〜10質量%が好ましい。上記光重合開始剤の含有量が0.1質量%より小さいと、露光による硬化が不十分になる場合があり、30質量%より大きいと、着色感光性組成物中に開始剤が析出する場合がある。 In the colored photosensitive composition of the present invention, the content of the radical photopolymerization initiator is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass in the colored photosensitive composition of the present invention. When the content of the photopolymerization initiator is less than 0.1% by mass, curing by exposure may be insufficient. When the content is more than 30% by mass, the initiator is precipitated in the colored photosensitive composition. There is.
本発明の着色感光性組成物は、必要に応じて有機溶媒に溶解又は分散させ、得られた塗液をスピンコーター、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塗布し、光照射して硬化させることができる。 The colored photosensitive composition of the present invention is dissolved or dispersed in an organic solvent as necessary, and the obtained coating liquid is spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, etc. It can be applied on a supporting substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. by a known means and cured by light irradiation.
上記有機溶媒としては、通常、必要に応じて上記の各成分を溶解又は分散しえる溶媒、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媒;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媒;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媒;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媒;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(PGMEA)、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媒;ベンゼン、トルエン、キシレン等のBTX系溶媒;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媒;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媒;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媒;クロロベンゼン等のハロゲン化芳香環含有炭化水素系溶媒;カルビトール系溶媒、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、水等が挙げられ、これらの溶媒は1種又は2種以上の混合溶媒として使用することができる。これらの中でもケトン類、エーテルエステル系溶媒等、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、シクロヘキサノン等が、着色感光性組成物においてレジストと光重合開始剤の相溶性がよいので好ましい。 The organic solvent is usually a solvent that can dissolve or disperse each of the above components as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone. Ketones such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether, etc .; methyl acetate, ethyl acetate, acetic acid-n-propyl, acetic acid Ester solvents such as isopropyl, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate and texanol; cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Alcohol solvents such as ethanol, 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 ( PGMEA), ether ester solvents such as dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate and ethoxyethyl propionate; BTX solvents such as benzene, toluene and xylene; aliphatics such as hexane, heptane, octane and cyclohexane Hydrocarbon solvents: terpene hydrocarbon oils such as turpentine oil, D-limonene, pinene, etc .; mineral spirits, swazol # 310 (Cosmo Matsuyama Oil Co., Ltd.), Solvesso # 100 (E Parachemical solvents such as Son Chemical Co., Ltd .; Halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; Halogenated aromatic ring-containing hydrocarbon systems such as chlorobenzene Solvent; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water, etc. These solvents can be used as one or a mixture of two or more. Among these, ketones, ether ester solvents, etc., particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility of the resist and the photopolymerization initiator is good in the colored photosensitive composition.
本発明の着色感光性組成物には、さらに着色剤を加えることができ、該着色剤としては、染料又は顔料が挙げられる。
上記染料としては、380〜1200nmに吸収を有する化合物であれば特に限定されないが、例えば、アゾ化合物、アントラキノン化合物、インジゴイド化合物、トリアリールメタン化合物、キサンテン化合物、アリザリン化合物、アクリジン化合物、スチルベン化合物、チアゾール化合物、ナフトール化合物、キノリン化合物、ニトロ化合物、インダミン化合物、オキサジン化合物、フタロシアニン化合物、シアニン化合物、ジインモニウム化合物、シアノエテニル化合物、ジシアノスチレン化合物、ローダミン化合物、ペリレン化合物、ポリエンナフトラクタム化合物、クマリン化合物、スクアリリウム化合物、クロコニウム化合物、スピロピラン化合物、スピロオキサジン化合物、メロシアニン化合物、オキソノール化合物、スチリル化合物、ピリリウム化合物、ローダニン化合物、オキサゾロン化合物、フタルイミド化合物、シンノリン化合物、ナフトキノン化合物、アザアントラキノン化合物、ポルフィリン化合物、アザポルフィリン化合物、ピロメテン化合物、キナクリドン化合物、ジケトピロロピロール化合物、インジゴ化合物、アクリジン化合物、アジン化合物、アゾメチン化合物、アニリン化合物、キナクリドン化合物、キノフタロン化合物、キノンイミン化合物、イリジウム錯体化合物、ユーロピウム錯体化合物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。A colorant can be further added to the colored photosensitive composition of the present invention, and examples of the colorant include dyes and pigments.
The dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm. For example, azo compounds, anthraquinone compounds, indigoid compounds, triarylmethane compounds, xanthene compounds, alizarin compounds, acridine compounds, stilbene compounds, thiazoles. Compound, naphthol compound, quinoline compound, nitro compound, indamine compound, oxazine compound, phthalocyanine compound, cyanine compound, diimmonium compound, cyanoethenyl compound, dicyanostyrene compound, rhodamine compound, perylene compound, polyenenaphtholactam compound, coumarin compound, squarylium compound, Croconium compounds, spiropyran compounds, spirooxazine compounds, merocyanine compounds, oxonol compounds, stiri Compound, pyrylium compound, rhodanine compound, oxazolone compound, phthalimide compound, cinnoline compound, naphthoquinone compound, azaanthraquinone compound, porphyrin compound, azaporphyrin compound, pyromethene compound, quinacridone compound, diketopyrrolopyrrole compound, indigo compound, acridine compound, azine Examples thereof include dyes such as compounds, azomethine compounds, aniline compounds, quinacridone compounds, quinophthalone compounds, quinoneimine compounds, iridium complex compounds, and europium complex compounds, and these may be used in combination.
上記顔料としては、無機顔料又は有機顔料を用いることができ、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、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、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以下のもの、950℃における揮発分中のCO、CO2から算出した全酸素量が、カーボンブラックの表面積100m2当たり9mg以上であるもの;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;疎水性樹脂、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、アンバー等の無機含量又は有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。As the pigment, inorganic pigments or organic pigments can be used, for example, nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, Isoindoline compounds, quinacridone compounds, anthanthrone compounds, perinone compounds, perylene compounds, diketopyrrolopyrrole compounds, thioindigo compounds, dioxazine compounds, triphenylmethane compounds, quinophthalone compounds, naphthalene tetracarboxylic acids; azo dyes, metal complex compounds of cyanine dyes Lake pigments; carbon black obtained by furnace method, channel method, thermal method, acetylene black, ketjen black or lamp black, etc. Carbon black: prepared by coating and coating the above carbon black with an epoxy resin, carbon black previously dispersed with a resin in a solvent and adsorbing 20 to 200 mg / g of resin, and the above carbon black being acidic or alkaline Surface treatment, average particle diameter of 8 nm or more, DBP oil absorption of 90 ml / 100 g or less, total oxygen amount calculated from CO and CO 2 in volatile matter at 950 ° C. is 9 mg or more per 100 m 2 of carbon black surface area Graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; hydrophobic resin, chromium oxide green, miloli blue , Koval Green, cobalt blue, manganese-based, ferrocyanide, phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron oxide (III)), An inorganic content or organic pigment such as cadmium red, synthetic iron black, or amber can be used. These pigments can be used alone or in combination.
上記無機顔料又は有機顔料としては、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 inorganic pigment or organic pigment, commercially available pigments 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, 3, 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.
本発明の着色感光性組成物において、上記色剤の含有量は、本発明の着色感光性組成物中、0〜99質量%、特に0〜80質量%が好ましい。 In the colored photosensitive composition of the present invention, the content of the colorant is preferably 0 to 99% by mass, particularly preferably 0 to 80% by mass in the colored photosensitive composition of the present invention.
本発明の着色感光性組成物には、更に無機化合物を含有させることができる。該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、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。 The colored photosensitive composition of the present invention can further contain an inorganic compound. 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; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Etc.
上記着色感光性組成物において、顔料及び/又は無機化合物を用いる場合、分散剤を加えることができる。該分散剤としては顔料、無機化合物を分散、安定化できるものであれば何でも良く、市販の分散剤、例えばビックケミー社製、BYKシリーズ等を用いることができ、塩基性官能基を有するポリエステル、ポリエーテル、ポリウレタンからなる高分子分散剤、塩基性官能基として窒素原子を有し、窒素原子を有する官能基がアミン、及び/又はその四級塩であり、アミン価が1〜100mgKOH/gのものが好適に用いられる。 In the colored photosensitive composition, when a pigment and / or an inorganic compound is used, a dispersant can be added. As the dispersant, any pigment or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie, Inc. can be used. Polymer dispersant made of ether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Are preferably used.
本発明の着色感光性組成物には、必要に応じて、p−アニソール、ハイドロキノン、ピロカテコール、t−ブチルカテコール、フェノチアジン等の熱重合抑制剤;可塑剤;接着促進剤;充填剤;消泡剤;レベリング剤;表面調整剤;フェノール系酸化防止剤、ホスファイト系酸化防止剤、チオエーテル系酸化防止剤等の酸化防止剤;紫外線吸収剤;分散助剤;凝集防止剤;触媒;効果促進剤;架橋剤;増粘剤等の慣用の添加物を加えることができる。 In the colored photosensitive composition of the present invention, if necessary, a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine, etc .; plasticizer; adhesion promoter; filler; Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as cross-linking agents; thickeners can be added.
また、上記酸価を有するエチレン性不飽和結合を有する重合性化合物とともに、他の有機重合体を用いることによって、本発明の着色感光性組成物の硬化物の特性を改善することもできる。上記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、ポリアミドイミド樹脂、ポリアミック酸樹脂、エポキシ樹脂等が挙げられ、これらの中でも、ポリスチレン、(メタ)アクリル酸−メチルメタクリレート共重合体、エポキシ樹脂が好ましい。 Moreover, the characteristic of the hardened | cured material of the colored photosensitive composition of this invention can also be improved by using another organic polymer with the polymeric compound which has the ethylenically unsaturated bond which has the said acid value. Examples of the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate. 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 Polyester, phenol resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, etc. are mentioned. Among these, polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, epoxy resin are used. Masui.
本発明の着色感光性組成物には、更に、熱ラジカル重合開始剤、連鎖移動剤、増感剤、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。 The colored photosensitive composition of the present invention may further contain a thermal radical polymerization initiator, a chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound, and the like.
上記熱ラジカル重合開始剤としては、2,2′−アゾビスイソブチロニトリル、2,2′−アゾビス(メチルイソブチレ−ト)、2,2’−アゾビス−2,4−ジメチルバレロニトリル、1,1’−アゾビス(1−アセトキシ−1−フェニルエタン)等のアゾ系開始剤;ベンゾイルパーオキサイド、ジ−t−ブチルベンゾイルパーオキサイド、t−ブチルパーオキシピバレート、ジ(4−t−ブチルシクロヘキシル)パーオキシジカーボネート等の過酸化物系開始剤、過硫酸アンモニウム、過硫酸ナトリウム、過硫酸カリウム等の過硫酸塩等が挙げられる。これらは一種又は二種以上を混合して用いることができる。 Examples of the thermal radical polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis (methylisobutyrate), 2,2'-azobis-2,4-dimethylvaleronitrile, Azo initiators such as 1′-azobis (1-acetoxy-1-phenylethane); benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate, di (4-t-butylcyclohexyl) ) Peroxide initiators such as peroxydicarbonate, and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.
上記連鎖移動剤、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、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 and sensitizer, a sulfur atom-containing compound is generally used. For example, thioglycolic acid, thiomalic 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-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol , 2-me Captoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3- Mercapto compounds such as mercaptopropionate), disulfide compounds obtained by oxidizing the mercapto compounds, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid, etc. Alkyl compound, trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol compounds such as trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, Showen Denko Karenz MT BD1, PE1, NR1, and the like.
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、これらは組み合わせて用いてもよい。 Examples of the surfactant include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents 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、イソシアネート基、メタクリロイル基、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. A ring agent is 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。これらのなかでも、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 part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of 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 as or different from each other. Moreover, the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used. Among these, alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
また、本発明の着色感光性組成物を硬化させる際に用いられる活性光の光源としては、波長300〜450nmの光を発光するものを用いることができ、例えば、超高圧水銀、水銀蒸気アーク、カーボンアーク、キセノンアーク等を用いることができる。 Moreover, as a light source of the active light used when hardening the colored photosensitive composition of this invention, what emits light with a wavelength of 300-450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, Carbon arc, xenon arc, etc. can be 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、アルゴンイオンレーザー、ヘリウムネオンレーザー、YAGレーザー、及び半導体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られる。これらのレーザーを使用する場合には、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 that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy. As the laser light, light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
本発明の着色感光性組成物(又はその硬化物)は、光硬化性塗料或いはワニス、光硬化性接着剤、プリント基板、或いはカラーテレビ、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パネル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、光造形用樹脂、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、液状及び乾燥膜の双方、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、めっき用マスク、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或い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 colored photosensitive composition of the present invention (or a cured product thereof) is a photocurable paint or varnish, a photocurable adhesive, a printed circuit board, a color television, a PC monitor, a personal digital assistant, a digital camera, or the like. Color filters for liquid crystal display panels, color filters for CCD image sensors, electrode materials for plasma display panels, powder coatings, printing inks, printing plates, adhesives, dental compositions, resin for stereolithography, gel coats, electronics Structures for manufacturing photoresists, electroplating resists, etching resists, both liquid and dry films, solder resists, color filters for various display applications or in the manufacturing process of plasma display panels, electroluminescent display devices, and LCDs Composition for encapsulating resist, electrical and electronic components for forming For manufacturing 3D objects by solder resist, magnetic recording materials, micro mechanical parts, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, screen printing stencils, stereolithography Materials, holographic recording materials, image recording materials, fine electronic circuits, decoloring materials, decoloring materials for image recording materials, decoloring materials for image recording materials using microcapsules, photoresist materials for printed wiring boards, UV and It can be used for various applications such as photoresist material for visible laser direct image system, photoresist material used for dielectric layer formation in sequential lamination of printed circuit boards or protective film, and there are no particular restrictions on its use .
本発明の着色感光性組成物は、カラーフィルタの画素を形成する目的で使用され、特に液晶表示パネル等の画像表示装置用の表示デバイス用カラーフィルタを形成するための感光性組成物として有用である。 The colored photosensitive composition of the present invention is used for the purpose of forming pixels of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel. is there.
上記表示デバイス用カラーフィルタは、(1)上記着色感光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活性光を照射する工程、(3)露光後の被膜を現像液にて現像する工程、(4)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。また、本発明の着色感光性組成物は、現像工程の無いインクジェット方式の着色感光性組成物としても有用である。 The color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition on a substrate, and (2) irradiating the coating film with active light through a mask having a predetermined pattern shape. It is preferably formed by a step, (3) a step of developing the film after exposure with a developer, and (4) a step of heating the film after development. In addition, the colored photosensitive composition of the present invention is also useful as an inkjet-type colored photosensitive composition without a development step.
以下、実施例等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。 Hereinafter, although an example etc. are given and the present invention is explained still in detail, the present invention is not limited to these examples.
[実施例1−1]化合物No.1の合成
<ステップ1>化合物4の合成
上記スキームにおいて、化合物3の1当量及びピリジン2.42gを混合し、化合物2の2.5当量及び4−ジメチルアミノピリジン2.42gを加えて氷浴下で30分撹拌し、EDC塩酸塩の4.5等量を加え、窒素雰囲気下、室温で5時間撹拌した。酢酸エチル/水で油水分離した後、水洗、乾燥し、溶媒を留去して化合物4を得た。<Step 1> Synthesis of Compound 4 In the above scheme, 1 equivalent of Compound 3 and 2.42 g of pyridine were mixed, 2.5 equivalents of Compound 2 and 2.42 g of 4-dimethylaminopyridine were added, and the mixture was added in an ice bath for 30. The mixture was stirred for 4 minutes, 4.5 equivalents of EDC hydrochloride was added, and the mixture was stirred at room temperature for 5 hours under a nitrogen atmosphere. After oil-water separation with ethyl acetate / water, washing with water and drying were performed, and the solvent was distilled off to obtain Compound 4.
<ステップ2>化合物No.1の合成
ステップ1で得られた化合物4の1当量及びピリジン2.05gを混合し、4−ジメチルアミノピリジン0.1当量を加えて撹拌した後、10℃以下で二炭酸−t−ブチルの12当量を滴下し、室温で20時間撹拌した。酢酸エチル/水で油水分離した後、水洗、乾燥し、溶媒を留去した。カラムクロマトグラフィー(酢酸エチル:ヘキサン=1:1)により精製し、メタノールから晶析を行い、化合物No.1を収率24%で得た。得られた化合物が目的物であることは1H−NMR、IRにて確認した。また、吸収波長特性を測定した。結果を[表1]及び[表2]に示す。<Step 2> Compound No. Synthesis of 1 1 equivalent of Compound 4 obtained in Step 1 and 2.05 g of pyridine were mixed, 0.1 equivalent of 4-dimethylaminopyridine was added and stirred, and then 10 ° C. or less of t-butyl dicarbonate was added. 12 equivalents were added dropwise and stirred at room temperature for 20 hours. After oil-water separation with ethyl acetate / water, the mixture was washed with water and dried, and the solvent was distilled off. Purification by column chromatography (ethyl acetate: hexane = 1: 1), crystallization from methanol, compound no. 1 was obtained in a yield of 24%. It was confirmed by 1 H-NMR and IR that the obtained compound was the target product. Moreover, the absorption wavelength characteristic was measured. The results are shown in [Table 1] and [Table 2].
[実施例1−2]化合物No.2の合成
<ステップ1>化合物6の合成
上記スキームにおいて、化合物5の1当量及びピリジン3.12gを混合し、4−ジメチルアミノピリジン0.1当量を加えて撹拌した後、10℃以下で二酸化−t−ブチルの3当量を滴下し、室温で3時間撹拌した。酢酸エチル/水で油水分離した後、水洗、乾燥し、溶媒を留去して化合物6を得た。<Step 1> Synthesis of Compound 6 In the above scheme, 1 equivalent of Compound 5 and 3.12 g of pyridine were mixed, 0.1 equivalent of 4-dimethylaminopyridine was added and stirred, and then -t- 3 equivalents of butyl were added dropwise and stirred at room temperature for 3 hours. After oil-water separation with ethyl acetate / water, washing with water and drying were performed, and the solvent was distilled off to obtain Compound 6.
<ステップ2>化合物No.2の合成
化合物7の1当量及び酢酸エチル10g、水10gを混合し、ステップ1で得られた化合物6の1当量を加えて撹拌した後、酢酸エチル層を取り分けて乾燥し、理論収量の5倍まで濃縮した。濃縮した酢酸エチル溶液をヘキサンに分散させて晶析し、化合物No.2を収率70%で得た。得られた化合物が目的物であることは1H−NMR、IRにて確認した。また、吸収波長特性を測定した。結果を[表1]及び[表2]に示す。<Step 2> Compound No. Synthesis of 2 1 equivalent of compound 7, 10 g of ethyl acetate and 10 g of water were mixed, 1 equivalent of compound 6 obtained in step 1 was added and stirred, and then the ethyl acetate layer was separated and dried to obtain a theoretical yield of 5 Concentrated to double. The concentrated ethyl acetate solution was dispersed in hexane and crystallized. 2 was obtained with a yield of 70%. It was confirmed by 1 H-NMR and IR that the obtained compound was the target product. Moreover, the absorption wavelength characteristic was measured. The results are shown in [Table 1] and [Table 2].
[実施例1−3]化合物No.3の合成
<ステップ1>化合物9の合成
上記スキームにおいて、化合物8の1当量、水酸化ナトリウム2eq.水2g、及びトルエン2gを混合し、室温で撹拌した。その後、氷冷下、1N塩酸水溶液2mLを加えて酸性溶液とし、油水分離を行い化合物9が含まれるトルエン溶液を得た。<Step 1> Synthesis of Compound 9 In the above scheme, 1 equivalent of Compound 8, sodium hydroxide 2 eq. 2 g of water and 2 g of toluene were mixed and stirred at room temperature. Then, 2 mL of 1N hydrochloric acid aqueous solution was added under ice-cooling to make an acidic solution, and oil-water separation was performed to obtain a toluene solution containing Compound 9.
<ステップ2>化合物No.3の合成
ステップ1で得られた化合物9の1当量が含まれるトルエン溶液にクロロホルム4g、化合物6の1eq.を加えて撹拌、油水分離を行った後、ヘキサンに分散させ晶析し、化合物No.3を収率80%で得た。得られた化合物が目的物であることは1H−NMR、IRにて確認した。また、吸収波長特性を測定した。結果を[表1]及び[表2]に示す。<Step 2> Compound No. 3 In a toluene solution containing 1 equivalent of the compound 9 obtained in Step 1, 4 g of chloroform and 1 eq. Was added, and the mixture was stirred and separated into oil and water. 3 was obtained in 80% yield. It was confirmed by 1 H-NMR and IR that the obtained compound was the target product. Moreover, the absorption wavelength characteristic was measured. The results are shown in [Table 1] and [Table 2].
[実施例2−2〜2−3]着色感光性組成物No.1〜No.3の調製
<ステップ1>感光性組成物No.1の調製
酸価を有するエチレン性不飽和結合を有する重合性化合物成分としてACA Z250(ダイセルサイテック社製)を30.3g、酸価を有しないエチレン性不飽和結合を有する重合性化合物成分としてアロニックスM−450(東亜合成社製)を11.04g、光ラジカル重合開始剤成分としてイルガキュア907(BASF社製)を1.93g、溶媒としてPGMEAを36.60g並びにシクロヘキサノンを20.08g、及び、その他成分としてFZ2122(東レ・ダウコーニング社製)を0.01g混合し、不溶物が無くなるまで撹拌し、感光性組成物No.1を得た。[Examples 2-2 to 2-3] Colored photosensitive composition No. 1-No. Preparation of Step 3 <Step 1> Photosensitive Composition No. Preparation of 1 30.3 g of ACA Z250 (manufactured by Daicel Cytec Co., Ltd.) as a polymerizable compound component having an ethylenically unsaturated bond having an acid value, and Aronix as a polymerizable compound component having an ethylenically unsaturated bond having no acid value 11.04 g of M-450 (manufactured by Toa Gosei Co., Ltd.), 1.93 g of Irgacure 907 (manufactured by BASF) as a photo radical polymerization initiator component, 36.60 g of PGMEA as a solvent, 20.08 g of cyclohexanone, and others As a component, 0.01 g of FZ2122 (manufactured by Toray Dow Corning Co., Ltd.) was mixed and stirred until insoluble matter disappeared. 1 was obtained.
<ステップ2>染料液No.1〜No.3の調製
上記で得られた化合物No.1〜No.3の0.10gに、ジメチルアセトアミド1.90gを加え、撹拌して溶解させて、染料液No.1〜No.3をそれぞれ調製した。<Step 2> Dye solution No. 1-No. Preparation of Compound No. 3 obtained above 1-No. 3. To 1.10 g of No. 3 was added 1.90 g of dimethylacetamide and dissolved by stirring. 1-No. 3 were prepared respectively.
<ステップ3>着色感光性組成物No.1〜No.3の調製
ステップ1で得られた感光性組成物No.1の5.0gとステップ2で得られた染料液No.1〜No.3の1.0gとをそれぞれ混合して均一になるまで撹拌し、本発明の着色感光性組成物No.1〜No.3をそれぞれ得た。<Step 3> Colored photosensitive composition No. 1-No. Preparation of photosensitive composition No. 3 obtained in step 1 1 of 5.0 g and the dye solution No. obtained in Step 2. 1-No. 3 and 1.0 g of each were mixed and stirred until uniform, and the colored photosensitive composition No. 1 of the present invention was stirred. 1-No. 3 were obtained respectively.
[比較例1−1〜1−3]比較着色性感光性組成物No.1〜No.3の調製
実施例2のステップ2における化合物No.1を下記の比較化合物No.1〜No.3の何れかに変更した以外は、実施例2−1と同様の手法で、比較着色感光性組成物No.1〜No.3を得た。[Comparative Examples 1-1 to 1-3] Comparative coloring photosensitive composition No. 1-No. Preparation of Compound No. 3 in Step 2 of Example 2 1 was compared with the following comparative compound No. 1. 1-No. Except for the change to any of No. 3, the comparative colored photosensitive composition No. 1 was prepared in the same manner as in Example 2-1. 1-No. 3 was obtained.
[比較例2−1〜2−3]比較着色性感光性組成物No.1A〜No.3Aの調製
比較着色性感光性組成物No.1〜No.3に酸化防止剤として下記化合物αを加えた以外は、実施例2−1と同様の手法で、比較着色感光性組成物No.1A〜No.3Aを得た。[Comparative Examples 2-1 to 2-3] Comparative coloring photosensitive composition No. 1A-No. Preparation of 3A Comparative coloring photosensitive composition No. 1-No. 3 was added in the same manner as in Example 2-1, except that the following compound α was added as an antioxidant. 1A-No. 3A was obtained.
[評価例1−1〜1−3並びに比較評価例1−1〜1−3]焼成による耐熱性評価
上記で得られた着色感光性組成物No.1〜No.3並びに比較着色感光性組成物No.1〜No.3をそれぞれガラス基板に410rpm×7secの条件で塗工し、ホットプレートで乾燥(90℃、90sec)させた。得られた塗膜に超高圧水銀ランプで露光(150mJ/cm2)した。露光後の塗膜を、230℃×30minの条件で焼成した。用いた化合物の極大吸収波長(λmax)における焼成前(露光後)の塗膜の吸光度と焼成後の塗膜の吸光度を測定し、焼成前(露光後)の塗膜の吸光度を100としたときの相対強度として評価した。尚、焼成後の塗膜の吸光度が100に近いほど耐熱性が高いことを示す。また、焼成前後の色差(ΔEab*)を調べた。結果を[表3]に示す。[Evaluation Examples 1-1 to 1-3 and Comparative Evaluation Examples 1-1 to 1-3] Evaluation of Heat Resistance by Firing The colored photosensitive composition No. obtained above. 1-No. 3 and comparative colored photosensitive composition no. 1-No. 3 was coated on a glass substrate under the condition of 410 rpm × 7 sec, and dried on a hot plate (90 ° C., 90 sec). The obtained coating film was exposed (150 mJ / cm 2 ) with an ultrahigh pressure mercury lamp. The coated film after exposure was baked under conditions of 230 ° C. × 30 min. When the absorbance of the coating film before firing (after exposure) and the absorbance of the coating film after firing at the maximum absorption wavelength (λmax) of the compound used are measured, and the absorbance of the coating film before firing (after exposure) is 100 Was evaluated as relative strength. In addition, it shows that heat resistance is so high that the light absorbency of the coating film after baking is close to 100. Further, the color difference (ΔE ab * ) before and after firing was examined. The results are shown in [Table 3].
上記結果より、本発明の着色感光性組成物は耐熱性が高いことは明らかである。 From the above results, it is clear that the colored photosensitive composition of the present invention has high heat resistance.
[評価例2−1〜2−3並びに比較評価例2−1〜2−3]酸化防止機能評価
先ず、着色感光性組成物No.1〜No.3に比較化合物No.1を加えた以外は、実施例2−1と同様の手法で、着色感光性組成物No.1A〜No.3Aをそれぞれ得た。
上記で得られた着色感光性組成物No.1A〜No.3A並びに比較例2−1〜2−3で得られた比較着色感光性組成物No.1A〜No.3Aをそれぞれガラス基板に410rpm×7secの条件で塗工し、ホットプレートで乾燥(90℃、90sec)させた。得られた塗膜に超高圧水銀ランプで露光(150mJ/cm2)した。
露光後の塗膜を、230℃×30minの条件で焼成した。用いた化合物の極大吸収波長(λmax)における焼成前(露光後)の塗膜の吸光度と焼成後の塗膜の吸光度を測定し、焼成前(露光後)の塗膜の吸光度を100としたときの相対強度として評価した。また、焼成前後の色差(ΔEab*)を調べた。結果を[表4]に示す。[Evaluation Examples 2-1 to 2-3 and Comparative Evaluation Examples 2-1 to 2-3] Evaluation of Antioxidation Function First, the colored photosensitive composition Nos. 1-No. 3 shows comparative compound no. 1 was added in the same manner as in Example 2-1, except that the colored photosensitive composition No. 1 was added. 1A-No. 3A was obtained respectively.
The colored photosensitive composition No. obtained above. 1A-No. 3A and comparative colored photosensitive composition Nos. Obtained in Comparative Examples 2-1 to 2-3. 1A-No. 3A was coated on a glass substrate under the condition of 410 rpm × 7 sec, and dried on a hot plate (90 ° C., 90 sec). The obtained coating film was exposed (150 mJ / cm 2 ) with an ultrahigh pressure mercury lamp.
The coated film after exposure was baked under conditions of 230 ° C. × 30 min. When the absorbance of the coating film before firing (after exposure) and the absorbance of the coating film after firing at the maximum absorption wavelength (λmax) of the compound used are measured, and the absorbance of the coating film before firing (after exposure) is 100 Was evaluated as relative strength. Further, the color difference (ΔE ab * ) before and after firing was examined. The results are shown in [Table 4].
上記結果より、従来の色素に本発明の化合物を加えた着色感光性組成物は、従来の色素に酸化防止剤を加えた比較着色感光性組成物に比べて耐熱性が高いことは明らかである。よってこれは本発明の化合物が高い酸化防止機能を有することを示している。 From the above results, it is clear that the colored photosensitive composition obtained by adding the compound of the present invention to the conventional dye has higher heat resistance than the comparative colored photosensitive composition obtained by adding the antioxidant to the conventional dye. . Therefore, this shows that the compound of the present invention has a high antioxidant function.
以上の結果より、本発明の新規化合物を用いた着色感光性組成物及びその硬化物における耐熱性が高いことは明白である。よって、本発明の染料及び着色感光性組成物は表示デバイス用カラーフィルタ及びそれを用いてなる液晶表示パネルに有用である。 From the above results, it is clear that the colored photosensitive composition using the novel compound of the present invention and the cured product thereof have high heat resistance. Therefore, the dye and the colored photosensitive composition of the present invention are useful for a color filter for a display device and a liquid crystal display panel using the same.
Claims (10)
(式中、R01、R02、R03、R04及びR05は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、炭素原子数1〜40のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基、炭素原子数2〜20の複素環含有基又は−O−R1を表し、
R01、R02、R03、R04及びR05のうち少なくとも1つは−O−R1で表され、
R1は、水素原子、炭素原子数1〜40のアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアリールアルキル基、炭素原子数2〜20の複素環含有基又はトリアルキルシリル基を表し、
R01、R02、R03、R04及びR05並びにR1で表されるアルキル基、アリール基、アリールアルキル基又は複素環含有基は、置換基を有しているか又は無置換であり、
R01、R02、R03、R04及びR05並びにR1で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素−炭素二重結合、−O−、−S−、−CO−、−O−CO−、−CO−O−、−O−CO−O−、−S−CO−、−CO−S−、−S−CO−O−、−O−CO−S−、−CO−NH−、−NH−CO−、−NH−CO−O−、−NR2−、>P=O、−S−S−又は−SO2−で置き換わっていてもよく、
R2は、水素原子又は炭素原子数1〜8のアルキル基を表す。)An organic dye having an absorption maximum in the ultraviolet to near-infrared wavelength region, and having 1 to 10 substituents represented by the following general formula (1) in the molecule.
(Wherein R 01 , R 02 , R 03 , R 04 and R 05 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms. , An aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a heterocyclic ring-containing group having 2 to 20 carbon atoms, or —O—R 1 ;
At least one of R 01 , R 02 , R 03 , R 04 and R 05 is represented by —O—R 1 ;
R 1 is a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a heterocycle-containing group having 2 to 20 carbon atoms, or Represents a trialkylsilyl group,
The alkyl group, aryl group, arylalkyl group or heterocyclic ring-containing group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 has a substituent or is unsubstituted,
The methylene group in the alkyl group or arylalkyl group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 is a carbon-carbon double bond, —O—, —S—, —CO. -, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH -, - NH- CO -, - NH-CO-O -, - NR 2 -,> P = O, -S-S- or -SO 2 - may be replaced by,
R 2 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. )
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