WO2023176609A1 - Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, capteur infrarouge, module de caméra et composé - Google Patents
Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, capteur infrarouge, module de caméra et composé Download PDFInfo
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- WO2023176609A1 WO2023176609A1 PCT/JP2023/008715 JP2023008715W WO2023176609A1 WO 2023176609 A1 WO2023176609 A1 WO 2023176609A1 JP 2023008715 W JP2023008715 W JP 2023008715W WO 2023176609 A1 WO2023176609 A1 WO 2023176609A1
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- group
- formula
- independently represent
- alkyl group
- hydrogen atom
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 381
- 239000000203 mixture Substances 0.000 title claims abstract description 167
- 230000003287 optical effect Effects 0.000 title claims abstract description 16
- 238000003384 imaging method Methods 0.000 title claims abstract description 11
- 239000006096 absorbing agent Substances 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 194
- 125000003118 aryl group Chemical group 0.000 claims description 164
- 229920005989 resin Polymers 0.000 claims description 134
- 239000011347 resin Substances 0.000 claims description 134
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 110
- 229910052757 nitrogen Inorganic materials 0.000 claims description 76
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 76
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000002252 acyl group Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 125000000732 arylene group Chemical group 0.000 claims description 26
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- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 13
- 125000002723 alicyclic group Chemical group 0.000 claims description 11
- 239000012528 membrane Substances 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- -1 oxygen radical Chemical class 0.000 description 111
- 239000010408 film Substances 0.000 description 86
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
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- 125000003277 amino group Chemical group 0.000 description 11
- 230000003078 antioxidant effect Effects 0.000 description 11
- 150000003839 salts Chemical group 0.000 description 11
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 125000004429 atom Chemical group 0.000 description 8
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 7
- 239000001062 red colorant Substances 0.000 description 7
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- 239000004593 Epoxy Substances 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
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- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
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- 229910052717 sulfur Inorganic materials 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001312 dry etching Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000001023 inorganic pigment Substances 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- 125000003566 oxetanyl group Chemical group 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
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- 229920001296 polysiloxane Polymers 0.000 description 5
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
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- 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 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
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- 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
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 3
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 2
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- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
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- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
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- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- ZBOYHAZRFJBUEL-UHFFFAOYSA-N n-[2-(4-benzhydryloxypiperidin-1-yl)ethyl]-3-hydroxy-5-(pyridin-3-ylmethoxy)naphthalene-2-carboxamide Chemical compound C1=CC=C2C=C(C(=O)NCCN3CCC(CC3)OC(C=3C=CC=CC=3)C=3C=CC=CC=3)C(O)=CC2=C1OCC1=CC=CN=C1 ZBOYHAZRFJBUEL-UHFFFAOYSA-N 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/435—Sulfonamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
Definitions
- the present invention relates to a composition containing a squarylium compound.
- the present invention also relates to a film, an optical filter, a solid-state image sensor, an image display device, an infrared sensor, a camera module, and a compound using the composition.
- CCDs charge-coupled devices
- CMOSs complementary metal oxide semiconductors
- These solid-state image sensors use silicon photodiodes sensitive to infrared rays in their light receiving portions. For this reason, an infrared cut filter may be provided to correct visibility.
- Infrared cut filters are manufactured using a composition containing an infrared absorber.
- Squarylium compounds and the like are known as infrared absorbers.
- Patent Document 1 describes that an infrared cut filter or the like is manufactured using a composition containing a specific squarylium compound or the like.
- squarylium compounds have an inner salt structure, they tend to have low solubility in solvents. For this reason, for compositions containing squarylium compounds, the squarylium compound tends to precipitate during storage of the composition, and when a film is formed using the composition after storage, foreign substances are likely to occur in the film. Therefore, there is room for further improvement in the storage stability of compositions containing squarylium compounds.
- an object of the present invention is to provide a composition that can form a film that has excellent storage stability and excellent light resistance. Further, the present invention provides a film, an optical filter, a solid-state image sensor, an image display device, an infrared sensor, a camera module, and a compound.
- a composition in which the infrared absorber includes a compound represented by formula (1);
- a and B each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle,
- R aa1 and R aa2 each independently represent a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an acyl group, an alkoxy
- R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group,
- R b11 and R b12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R b13 to R b21 each independently represent an alkyl group, an aryl group, or a heterocyclic group
- Y 1 to Y 4 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, or a group represented by formula (Y-1)
- m1 represents an integer from 0 to mA
- mA represents the maximum integer in which R
- Rz 11 represents an alkyl group or an aryl group
- Rz 12 represents a hydrogen atom, -COR 100 or -COOR 100
- R 100 represents a hydrogen atom, an alkyl group or an aryl group
- Rz 12a represents an alkyl group
- mz represents an integer from 0 to 4
- Rz 13 to Rz 16 each independently represent an alkyl group
- Rz 17 represents a hydrogen atom, an alkyl group, or an oxygen radical
- Rz 18 and Rz 19 each independently represent an alkyl group or an aryl group
- W 1 represents a single bond, an alkylene group, an arylene group, or -CO-
- Rz 20 represents a hydrogen atom, an alkyl group, an aryl group, or -COR 101
- R 101 represents
- composition according to ⁇ 1> wherein the compound represented by formula (1) is a compound represented by formula (2);
- R a1 to R a4 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocycle.
- R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R a13 to R a15 each independently represent an alkyl group, an aryl group, or a heterocyclic group
- R b1 to R b4 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an acyl group.
- R a1 and Y 1 may be combined to form a 5-membered or 6-member
- composition according to ⁇ 1> wherein the compound represented by formula (1) is a compound represented by formula (3);
- R 13 to R 17 and R 23 to R 27 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, or an alkyl group.
- R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R a13 to R a15 each independently represent an alkyl group, an aryl group, or a heterocyclic group
- R 11 , R 12 , R 21 and R 22 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocycle group, alkoxy group, acyl group, alkoxycarbonyl group, -NR b
- At least one of R 11 and R 12 and at least one of R 21 and R 22 in the above formula (3) are each independently -NHCOR b13 , and R b13 is an alkyl group, an aryl group, or , the composition according to ⁇ 3>, which is a heterocyclic group.
- At least one of R 11 and R 12 and at least one of R 21 and R 22 in the above formula (3) are each independently -NHSO 2 R b14 , and R b14 is an alkyl group, an aryl group , or the composition according to ⁇ 3>, which is a heterocyclic group.
- ⁇ 6> The composition according to any one of ⁇ 1> to ⁇ 5>, wherein the curable compound contains a resin.
- ⁇ 9> A film obtained using the composition according to any one of ⁇ 1> to ⁇ 8>.
- An optical filter comprising the film according to ⁇ 9>.
- a solid-state imaging device comprising the film according to ⁇ 9>.
- An infrared sensor comprising the film according to ⁇ 9>.
- ⁇ 15> Compound represented by formula (1);
- a and B each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle
- R aa1 and R aa2 each independently represent a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an acyl group, an alkoxy
- R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R a13 to R a15 each independently represent an alkyl
- R b11 and R b12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R b13 to R b21 each independently represent an alkyl group, an aryl group, or a heterocyclic group
- Y 1 to Y 4 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, or a group represented by formula (Y-1)
- m1 represents an integer from 0 to mA
- mA represents the maximum integer in which R
- Rz 11 represents an alkyl group or an aryl group
- Rz 12 represents a hydrogen atom, -COR 100 or -COOR 100
- R 100 represents a hydrogen atom, an alkyl group or an aryl group
- Rz 12a represents an alkyl group
- mz represents an integer from 0 to 4
- Rz 13 to Rz 16 each independently represent an alkyl group
- Rz 17 represents a hydrogen atom, an alkyl group, or an oxygen radical
- Rz 18 and Rz 19 each independently represent an alkyl group or an aryl group
- W 1 represents a single bond, an alkylene group, an arylene group, or -CO-
- Rz 20 represents a hydrogen atom, an alkyl group, an aryl group, or -COR 101
- R 101 represents
- the present invention it is possible to provide a composition that can form a film that has excellent storage stability and excellent light resistance. Further, the present invention can provide a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor, a camera module, and a compound.
- FIG. 1 is a schematic diagram showing one embodiment of an infrared sensor.
- ⁇ is used to include the numerical values described before and after it as a lower limit and an upper limit.
- the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the term "alkyl group” includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- the light used for exposure include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays typified by excimer laser, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- EUV light extreme ultraviolet rays
- (meth)acrylate” represents acrylate and/or methacrylate
- (meth)acrylic represents both acrylic and/or methacrylic
- (meth)acrylate” represents acrylic and/or methacrylate.
- Acryloyl refers to either or both of acryloyl and methacryloyl.
- the weight average molecular weight and number average molecular weight are defined as polystyrene equivalent values measured by gel permeation chromatography (GPC).
- GPC gel permeation chromatography
- Me in the chemical formula represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- infrared rays refer to light (electromagnetic waves) with a wavelength of 700 to 2,500 nm.
- the total solid content refers to the total mass of all components of the composition excluding the solvent.
- the term "process” is used not only to refer to an independent process, but also to include a process in which the intended effect of the process is achieved even if the process cannot be clearly distinguished from other processes. .
- composition of the present invention includes an infrared absorber, a curable compound, and a solvent,
- the above-mentioned infrared absorber is characterized by containing a compound represented by formula (1).
- the composition of the present invention has excellent storage stability and can form a film in which the generation of foreign matter is suppressed even after long-term storage. Further, according to the present invention, a film having excellent light resistance can be formed. Although the detailed reason for obtaining such an effect is unknown, it is presumed to be due to the following reasons.
- At least one of Y 1 to Y 4 is a group represented by formula (Y-1), and R aa1 and Y 1 , At least one selected from R aa1 and Y 2 , R aa2 and Y 3 , and R aa2 and Y 4 are combined to form a 5- or 6-membered heterocycle containing at least one nitrogen atom. It is presumed that this structure improves compatibility with the solvent and curable compound contained in the composition, resulting in a composition with excellent storage stability. Ru. Furthermore, squarylium compounds tend to easily form H associations in the film during film formation.
- H associations tends to reduce light resistance, but the compound represented by formula (1) has the above-mentioned structure, so it is difficult to form H associations in the film. It is assumed that this can be suppressed. Therefore, by using the composition of the present invention, a film with excellent light resistance can be formed.
- the composition of the present invention can be used as a composition for optical filters.
- Types of optical filters include infrared cut filters and infrared transmission filters. Since the compound represented by formula (1) can suppress the formation of H associations in the film, by using the composition of the present invention, a film with excellent visible light transmittance and excellent infrared shielding properties can be formed. You can also. Therefore, the composition of the present invention is particularly preferably used as a composition for an infrared cut filter.
- the composition of the invention includes an infrared absorber.
- the infrared absorber contained in the composition of the present invention includes a compound represented by formula (1).
- the compound represented by formula (1) is also a compound of the present invention.
- the compound represented by formula (1) will also be referred to as a specific compound.
- a and B in formula (1) each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle.
- the number of carbon atoms constituting the aromatic hydrocarbon ring is preferably 6 to 48, more preferably 6 to 22, and particularly preferably 6 to 12.
- the aromatic hydrocarbon ring is preferably a monocyclic ring or a condensed ring having 2 to 8 condensed rings, more preferably a monocyclic ring or a condensed ring having 2 to 4 condensed rings, It is more preferably a fused ring with 2 or 3 rings, even more preferably a monocyclic ring or a fused ring with 2 fused rings, and particularly preferably a monocyclic ring.
- the aromatic heterocycle is preferably a 5-membered ring or a 6-membered ring.
- the aromatic heterocycle is preferably a single ring or a condensed ring having 2 to 8 condensed rings, more preferably a monocycle or a condensed ring having 2 to 4 condensed rings, and is preferably a monocycle or a condensed ring having 2 to 4 condensed rings. or 3 fused rings, even more preferably a monocyclic ring or 2 fused rings, particularly preferably a monocyclic ring.
- the heteroatom constituting the ring of the aromatic heterocycle include nitrogen atom, oxygen atom, and sulfur atom, with nitrogen atom and sulfur atom being preferred.
- the number of heteroatoms constituting the ring of the aromatic heterocycle is preferably 1 to 3, more preferably 1 to 2.
- At least one of A and B is a benzene ring, a thiophene ring, a furan ring, a pyrrole ring, a pyridine ring, an azulene ring, or a fused ring containing these rings. It is preferable.
- Examples of the above-mentioned condensed rings include a naphthalene ring, a benzothiophene ring, a benzofuran ring, an isobenzofuran ring, a benzimidazole ring, an indole ring, an isoindole ring, a quinoline ring, an isoquinoline ring, a thienopyrrole ring, and a pyrrolothiazole ring.
- At least one of A and B is preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring.
- R aa1 and R aa2 in formula (1) each independently represent a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group , represents an acyl group, an alkoxycarbonyl group, -NR a11 R a12 , -SR a13 , -SO 2 R a14 , or -OSO 2 R a15 , R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, R a13 to R a15 each independently represent an alkyl group, an aryl group, or a heterocyclic group.
- Examples of the halogen atom represented by R aa1 and R aa2 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the number of carbon atoms in the alkyl group represented by R aa1 , R aa2 , R a11 to R a15 is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched, or cyclic, and preferably linear or branched.
- the above alkyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T, including aryl groups, heterocyclic groups, halogen atoms, sulfo groups, hydroxy groups, cyano groups, nitro groups, carboxy groups, phosphoric acid groups, and amino groups. It is preferable that it is at least one selected from the group consisting of:
- the number of carbon atoms in the aryl group represented by R aa1 , R aa2 , R a11 to R a15 is preferably 6 to 48, more preferably 6 to 22, even more preferably 6 to 12.
- the above aryl group may have a substituent.
- substituents include the groups listed below for substituent T, including alkyl groups, heterocyclic groups, halogen atoms, sulfo groups, hydroxy groups, cyano groups, nitro groups, carboxy groups, phosphoric acid groups, and amino groups. It is preferable that it is at least one selected from the group consisting of:
- the heterocyclic group represented by R aa1 , R aa2 , R a11 to R a15 is preferably a 5-membered or 6-membered heterocyclic group. Further, the heterocyclic group is preferably a monocyclic heterocyclic group or a fused ring heterocyclic group having 2 to 8 condensed rings; is more preferred, and a monocyclic heterocyclic group or a fused ring heterocyclic group having 2 or 3 condensed rings is even more preferred.
- the heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3, more preferably 1 to 2.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 30, more preferably 1 to 18, even more preferably 1 to 12.
- the above heterocyclic group may have a substituent.
- substituent T such as an alkyl group, an aryl group, a heterocyclic group, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, and Preferably, it is at least one selected from the group consisting of amino groups.
- the number of carbon atoms in the alkoxy group represented by R aa1 and R aa2 is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkoxy group is preferably linear or branched.
- the above alkoxy group may have a substituent.
- substituents include the groups listed below for substituent T, such as an alkyl group, an aryl group, a heterocyclic group, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, and Preferably, it is at least one selected from the group consisting of amino groups.
- the number of carbon atoms in the acyl group represented by R aa1 and R aa2 is preferably 2 to 30, more preferably 2 to 15, even more preferably 2 to 8.
- the acyl group include a formyl group, an alkylcarbonyl group, and an arylcarbonyl group.
- the number of carbon atoms in the alkylcarbonyl group is preferably 2 to 30, more preferably 2 to 15, even more preferably 2 to 8.
- the number of carbon atoms in the arylcarbonyl group is preferably 7 to 30, more preferably 7 to 20, and even more preferably 7 to 12.
- the above acyl group may have a substituent.
- substituent T examples include the groups listed below for substituent T, such as an alkyl group, an aryl group, a heterocyclic group, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, and Preferably, it is at least one selected from the group consisting of amino groups.
- the number of carbon atoms in the alkoxycarbonyl group represented by R aa1 and R aa2 is preferably 2 to 30, more preferably 2 to 15, and even more preferably 2 to 8.
- the alkoxycarbonyl group described above may have a substituent.
- substituent T such as an alkyl group, an aryl group, a heterocyclic group, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, and Preferably, it is at least one selected from the group consisting of amino groups.
- m1 in formula (1) represents an integer from 0 to mA
- mA represents the maximum integer in which R aa1 can be replaced with A
- m2 represents an integer from 0 to mB
- mB represents the maximum integer in which R aa2 can be replaced with B
- m1 is 2 or more
- two R aa1s out of m1 R aa1s may combine to form a ring
- m2 is 2 or more
- two R aa2s out of m2 R aa2s may be bonded to each other to form a ring.
- A is a benzene ring
- mA is 2.
- m1 and m2 are preferably each independently an integer of 0 to 2, more preferably 1 or 2.
- R b1 to R b4 in formula (1) each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocyclic group , alkoxy group, acyl group, alkoxycarbonyl group, -NR b11 R b12 , -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SR b16 , -SO 2 R b17 , -OSO 2 R b18 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 , R b11 and R b12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, R b13 to
- the halogen atom, alkoxy group, acyl group, and alkoxycarbonyl group represented by R b1 to R b4 are the same as the halogen atom, alkoxy group, acyl group, and alkoxycarbonyl group represented by R aa1 and R aa2 , and the preferred ranges are also the same. be.
- the alkyl group, aryl group, and heterocyclic group represented by R b1 to R b4 and R b11 to R b21 are the same as the alkyl group, aryl group, and heterocyclic group represented by R aa1 and R aa2 , and the preferred ranges are also the same. be.
- the alkyl group represented by R b11 to R b21 is also preferably a fluoroalkyl group because visible light transmittance and infrared shielding property can be further improved.
- At least one of R b1 and R b2 and at least one of R b3 and R b4 are each independently -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SO 2 R b17 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 are preferable, and -NHCOR b13 or -NHSO 2 R b14 is more preferable because visible light transmittance and infrared shielding property can be further improved, - More preferred is NHCOR b13 .
- R b13 , R b14 , R b15 , R b17 , R b19 , R b20 and R b21 are each independently preferably an alkyl group or an aryl group, more preferably an alkyl group, and have visible light transmittance. Further, a fluoroalkyl group is more preferable because it can further improve infrared shielding properties.
- one of R b1 and R b2 is -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SO 2 R b17 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 , and the other is hydrogen an atom
- one of R b3 and R b4 is -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SO 2 R b17 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 , and the other is hydrogen It is preferable that they are atoms, one of R b1 and R b2 is -NHCOR b13 or -NHSO 2 R b14 , the other is a hydrogen atom, and one of R b3 and R b4 is -NHCOR
- Y 1 to Y 4 in formula (1) each independently represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, or a group represented by formula (Y-1), R aa1 and Y 1 may be combined to form a 5-membered or 6-membered heterocycle containing at least one nitrogen atom, R aa1 and Y 2 may be combined to form a 5-membered or 6-membered heterocycle containing at least one nitrogen atom, R aa2 and Y 3 may be combined to form a 5-membered or 6-membered heterocycle containing at least one nitrogen atom, R aa2 and Y 4 may be combined to form a 5-membered or 6-membered heterocycle containing at least one nitrogen atom, Y 1 and Y 2 may be combined to form a 5-membered or 6-membered heterocycle containing at least one nitrogen atom, Y 3 and Y 4 may be combined to form a 5-membered or 6-membered heterocycle containing
- Y 1 to Y 4 is a group represented by formula (Y-1), and R aa1 and Y 1 , R aa1 and Y 2 , R aa2 and Y 3 , and R aa2 and Y 4 are combined to form a 5- or 6-membered heterocycle containing at least one nitrogen atom.
- the alkyl group, aryl group, and heterocyclic group represented by Y 1 to Y 4 in formula (1) are the same as the alkyl group, aryl group, and heterocyclic group represented by R aa1 and R aa2 , and the preferred ranges are also the same. .
- At least one of Y 1 and Y 2 and at least one of Y 3 and Y 4 are each independently a group represented by formula (Y-1).
- Ry 1 to Ry 4 in formula (Y-1) each independently represent a hydrogen atom, an alkyl group, or an aryl group.
- the number of carbon atoms in the alkyl group represented by Ry 1 to Ry 4 is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched, or cyclic, and preferably linear or branched.
- the above alkyl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
- the number of carbon atoms in the aryl group represented by Ry 1 to Ry 4 is preferably 6 to 48, more preferably 6 to 22, and even more preferably 6 to 12.
- the above aryl group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
- Ry 1 to Ry 4 are preferably hydrogen atoms.
- X 1 in formula (Y-1) is a single bond, an alkylene group, an arylene group, -O-, -S-, -NRx-, -CO-, -CS-, -SO-, or -SO 2 - or a combination of two or more selected from alkylene group, arylene group, -O-, -S-, -NRx-, -CO-, -CS-, -SO-, and -SO 2 - Rx represents a hydrogen atom, an alkyl group or an aryl group.
- Z 1 is a group represented by formula (Z-1) or a group represented by formula (Z-4)
- the part in X 1 that connects to Z 1 is an alkylene group or an arylene group. .
- the alkylene group represented by X 1 preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 1 to 8 carbon atoms.
- the number of carbon atoms in the arylene group represented by X 1 is preferably 6 to 48, more preferably 6 to 22, and even more preferably 6 to 12.
- the number of carbon atoms in the alkyl group represented by Rx is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched, or cyclic, and preferably linear or branched.
- the number of carbon atoms in the aryl group represented by Rx is preferably 6 to 48, more preferably 6 to 22, and even more preferably 6 to 12.
- X 1 in formula (Y-1) is preferably a group represented by formula (X-1). *1 -X 11 -X 12 -X 13 - *2 ...(X-1) *1 and *2 represent bonds, and *2 is a bond with Z1 .
- X 11 and X 13 are each independently a single bond, -O-, -S-, -NRx-, -NRxCO-, -CONRx-, -CO-, -OCO-, -COO-, -CS-, -SO- or -SO 2 -, Rx represents a hydrogen atom, an alkyl group or an aryl group, X 12 represents a single bond, an alkylene group or an arylene group.
- Z 1 in formula (Y-1) is a group represented by formula (Z-1) or a group represented by formula (Z-4)
- X 12 is an alkylene group or an arylene group
- X 13 is a single bond.
- X 11 and X 13 are each independently a single bond, -O-, -NRx-, -NRxCO-, -CONRx-, -CO-, -OCO-, or.
- X 12 is a single bond or an alkylene group.
- Z 1 in formula (Y-1) is an alicyclic hydrocarbon group, aromatic hydrocarbon group or heterocyclic group, from the viewpoint of storage stability and light resistance, X 13 is -O- It is preferable.
- Z 1 in formula (Y-1) is a group represented by formula (Z-6) and W 1 is -CO-, X 12 is an alkylene group or an arylene group. , X 13 is preferably a single bond.
- Z 1 in formula (Y-1) represents an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, or a group represented by any one of formulas (Z-1) to (Z-6). .
- the alicyclic hydrocarbon group represented by Z 1 may be a monocyclic alicyclic hydrocarbon group or a polycyclic alicyclic hydrocarbon group. Further, the polycyclic alicyclic hydrocarbon group may have a crosslinked structure or a spirocyclic structure.
- the alicyclic hydrocarbon group may have a substituent. Examples of the substituent include the groups listed below for substituent T, and preferred are an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an acyloxy group.
- the aromatic hydrocarbon group represented by Z 1 may be a monocyclic aromatic hydrocarbon group or a condensed ring aromatic hydrocarbon group.
- the aromatic hydrocarbon group preferably has 6 to 48 carbon atoms, more preferably 6 to 22 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aromatic hydrocarbon group may have a substituent. Examples of the substituent include the groups listed below for substituent T, and preferred are an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, or an acyloxy group.
- the heterocyclic group represented by Z 1 is preferably a 5-membered or 6-membered heterocyclic group.
- the heterocyclic group is preferably a monocyclic heterocyclic group or a fused ring heterocyclic group having 2 to 8 fused rings, more preferably a monocyclic heterocyclic group or a fused ring heterocyclic group having 2 to 4 fused rings.
- a monocyclic heterocyclic group or a fused ring heterocyclic group having 2 or 3 condensed rings is more preferable.
- the heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3, more preferably 1 to 2.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 30, more preferably 1 to 18, even more preferably 1 to 12.
- the heterocyclic group may have a substituent. Examples of the substituent include the groups listed below for substituent T.
- Rz 11 represents an alkyl group or an aryl group
- Rz 12 represents a hydrogen atom, -COR 100 or -COOR 100
- R 100 represents a hydrogen atom, an alkyl group or an aryl group
- Rz 12a represents an alkyl group
- mz represents an integer from 0 to 4
- Rz 13 to Rz 16 each independently represent an alkyl group
- Rz 17 represents a hydrogen atom, an alkyl group, or an oxygen radical
- Rz 18 and Rz 19 each independently represent an alkyl group or an aryl group
- W 1 represents a single bond, an alkylene group, an arylene group, or -CO-
- Rz 20 represents a hydrogen atom, an alkyl group, an aryl group, or -COR 101
- R 101 represents an alkyl group
- Rz 11 in formula (Z-1) represents an alkyl group or an aryl group, and is preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 15, even more preferably 1 to 8.
- the alkyl group may be linear, branched, or cyclic. Further, the alkyl group may be unsubstituted or may have a substituent. Examples of the substituent include the groups listed below for substituent T.
- the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. Further, the aryl group may be unsubstituted or may have a substituent. Examples of the substituent include the groups listed below for substituent T.
- Rz 12 in formula (Z-2) represents a hydrogen atom, -COR 100 or -COOR 100
- R 100 represents a hydrogen atom, an alkyl group or an aryl group
- Rz 12a represents an alkyl group
- mz represents an integer from 0 to 4.
- Rz 12 is preferably a hydrogen atom.
- the alkyl group and aryl group represented by R 100 are the same as those described for Rz 11 .
- mz represents an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 1 or 2.
- the number of carbon atoms in the alkyl group represented by Rz 12a is preferably 1 to 10, more preferably 1 to 5.
- the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably branched.
- Rz 13 to Rz 16 in formula (Z-3) each independently represent an alkyl group, and Rz 17 represents a hydrogen atom, an alkyl group, or an oxygen radical (-O.).
- the number of carbon atoms in the alkyl group represented by Rz 13 to Rz 17 is preferably 1 to 10, more preferably 1 to 5.
- the alkyl group may be linear, branched, or cyclic, and preferably linear or branched.
- Rz 18 and Rz 19 each independently represent an alkyl group or an aryl group, and preferably an aryl group.
- the alkyl group and aryl group represented by Rz 18 and Rz 19 are the same as those described for Rz 11 .
- W 1 represents a single bond, an alkylene group, an arylene group, or -CO-
- Rz 20 represents a hydrogen atom, an alkyl group, an aryl group, or -COR 101
- R 101 represents an alkyl group Or represents an aryl group.
- the alkylene group represented by W 1 preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and still more preferably 1 to 8 carbon atoms.
- the number of carbon atoms in the arylene group represented by W 1 is preferably 6 to 48, more preferably 6 to 22, and even more preferably 6 to 12.
- W 1 is preferably -CO-.
- Rz 20 is preferably a hydrogen atom, an alkyl group or -COR 101 , and more preferably a hydrogen atom.
- the alkyl group and aryl group represented by R 101 are the same as those described for Rz 11 .
- Z 1 in formula (Y-1) is preferably a group represented by any one of formulas (Z-1) to (Z-6); It is more preferably a group represented by either formula (Z-4), even more preferably a group represented by formula (Z-2) or formula (Z-4), ) is particularly preferable.
- Y 1 and Y 2 and one of Y 3 and Y 4 of formula (1) are each independently a group represented by formula (Y-1)
- Y 1 and Y Z 1 in the group represented by formula (Y-1) represented by either one of Y 3 and Y 2 and Z 1 in the group represented by formula (Y-1) represented by either Y 3 and Y 4 are, They may be the same or different.
- one Z 1 is a group represented by formula (Z-1) or formula (Z-4)
- the other Z 1 is a group represented by formula (Z-2).
- the specific compound may include a compound that has a resonance relationship; however, in the present invention, the specific compound (the compound represented by formula (1)) ) includes its resonance structure.
- the specific compound is preferably a compound represented by formula (2).
- R a1 to R a4 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocycle.
- R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R a13 to R a15 each independently represent an alkyl group, an aryl group, or a heterocyclic group
- R b1 to R b4 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an acyl group.
- R a1 and Y 1 may be combined to form a 5-membered or 6-membered
- R b1 to R b4 in formula (2) have the same meanings as R b1 to R b4 in formula (1).
- Y 1 to Y 4 in formula (2) have the same meanings as Y 1 to Y 4 in formula (1).
- the halogen atom, alkoxy group, acyl group, and alkoxycarbonyl group represented by R a1 to R a4 in formula (2) are the halogen atom, alkoxy group, acyl group, and alkoxycarbonyl group represented by R aa1 and R aa2 in formula (2).
- the preferred ranges are also the same.
- the alkyl group, aryl group, and heterocyclic group represented by R a1 to R a4 and R a11 to R a15 in formula (2) are the alkyl group, aryl group, and heterocyclic group represented by R aa1 and R aa2 in formula (1).
- the preferred ranges are also the same.
- At least one of R b1 and R b2 and at least one of R b3 and R b4 are each independently -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SO 2 R b17 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 are preferable, and -NHCOR b13 or -NHSO 2 R b14 is more preferable because visible light transmittance and infrared shielding property can be further improved, - More preferred is NHCOR b13 .
- R b13 , R b14 , R b15 , R b17 , R b19 , R b20 and R b21 are each independently preferably an alkyl group or an aryl group, more preferably an alkyl group, and have visible light transmittance. Further, a fluoroalkyl group is more preferable because it can further improve infrared shielding properties.
- one of R b1 and R b2 is -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SO 2 R b17 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 , and the other is hydrogen an atom
- one of R b3 and R b4 is -NHCOR b13 , -NHSO 2 R b14 , -NHCSNHR b15 , -SO 2 R b17 , -NHCSR b19 , -NHCONHR b20 or -NHCOOR b21 , and the other is hydrogen It is preferable that they are atoms, one of R b1 and R b2 is -NHCOR b13 or -NHSO 2 R b14 , the other is a hydrogen atom, and one of R b3 and R b4 is -NHCOR
- At least one of Y 1 to Y 4 is a group represented by formula (Y-1), and R a1 and Y 1 , R a2 and Y 2 , R a3 and Y 3 , At least one selected from R a4 and Y 4 is bonded to form a 5-membered or 6-membered heterocycle containing at least one nitrogen atom.
- At least one of Y 1 and Y 2 and at least one of Y 3 and Y 4 are each independently a group represented by formula (Y-1).
- R a2 and Y 2 combine to form a 5- or 6-membered heterocycle containing at least one nitrogen atom
- R a4 and Y 4 combine to form a 5- or 6-membered heterocycle containing at least one nitrogen atom.
- R a2 and Y 2 are bonded to form a 5-membered ring containing at least one nitrogen atom.
- a heterocycle is formed, and that R a4 and Y 4 are bonded to form a 5-membered heterocycle containing at least one nitrogen atom.
- At least one of Y 1 and Y 3 is a group represented by formula (Y-1) (preferably, Y 1 and Y 3 are each independently represented by formula (Y-1)); ), R a2 and Y 2 combine to form a 5- or 6-membered heterocycle (preferably a 5-membered heterocycle) containing at least one nitrogen atom. , R a4 and Y 4 are preferably bonded to form a 5- or 6-membered heterocycle (preferably a 5-membered heterocycle) containing at least one nitrogen atom.
- the specific compound is preferably a compound represented by formula (3).
- R 13 to R 17 and R 23 to R 27 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, or an alkyl group.
- R a11 and R a12 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group
- R a13 to R a15 each independently represent an alkyl group, an aryl group, or a heterocyclic group
- R 11 , R 12 , R 21 and R 22 each independently represent a hydrogen atom, a halogen atom, a sulfo group, a hydroxy group, a cyano group, a nitro group, a carboxy group, a phosphoric acid group, an alkyl group, an aryl group, a heterocycle group, alkoxy group, acyl group, alkoxycarbonyl group, -NR b
- the halogen atom, alkoxy group, acyl group, and alkoxycarbonyl group represented by R 13 to R 17 and R 23 to R 27 in formula (3) are the halogen atom, alkoxy group, and alkoxy group represented by R aa1 and R aa2 in formula (1), It is the same as the acyl group and the alkoxycarbonyl group, and the preferred ranges are also the same.
- the alkyl group, aryl group, and heterocyclic group represented by R 13 to R 17 , R 23 to R 27 , and R a11 to R a15 in formula (3) are the alkyl group represented by R aa1 and R aa2 in formula (1), It is the same as the aryl group and the heterocyclic group, and the preferred range is also the same.
- the halogen atom, alkoxy group, acyl group and alkoxycarbonyl group represented by R 11 , R 12 , R 21 and R 22 in formula (3) are the halogen atom, alkoxy group represented by R b1 to R b4 in formula (1), It is the same as the acyl group and the alkoxycarbonyl group, and the preferred ranges are also the same.
- the alkyl group, aryl group, and heterocyclic group represented by R 11 , R 12 , R 21 , R 22 , R b13 to R b21 in formula (3) are the alkyl group represented by R b1 to R b4 in formula (1), It is the same as the aryl group and the heterocyclic group, and the preferred range is also the same.
- At least one of R 11 and R 12 and at least one of R 21 and R 22 are each independently -NHCOR b13 , or at least one of R 11 and R 12 and R
- at least one of R 21 and R 22 is each independently -NHSO 2 R b14
- at least one of R 11 and R 12 and at least one of R 21 and R 22 are each independently -NHCOR b13 is more preferred.
- R 11 and R 12 is -NHCOR b13 and the other is a hydrogen atom
- one of R 21 and R 22 is -NHCOR b13 and the other is a hydrogen atom
- R 11 and R 12 is -NHSO 2 R b14 and the other is a hydrogen atom
- one of R 21 and R 22 is -NHSO 2 R b14 and the other is a hydrogen atom
- R 11 and R 12 It is more preferable that one of R 21 and R 22 is -NHCOR b13 and the other is a hydrogen atom
- one of R 21 and R 22 is -NHCOR b13 and the other is a hydrogen atom.
- the alkyl group, aryl group, heterocyclic group represented by Y 11 and Y 21 in formula (3) and the group represented by formula (Y-1) are the alkyl group represented by Y 1 to Y 4 in formula (1).
- group, aryl group, heterocyclic group, and group represented by formula (Y-1), and the preferred ranges are also the same. It is preferable that Y 11 and Y 21 in formula (3) are each independently a group represented by formula (Y-1).
- Z 1 of both formulas (Y-1) may be the same or different. You can leave it there.
- one Z 1 is a group represented by formula (Z-1) or formula (Z-4), and the other Z 1 is a group represented by formula (Z-2). ), formula (Z-3) or formula (Z-6).
- substituent T examples include the following groups.
- Halogen atom e.g. fluorine atom, chlorine atom, bromine atom, iodine atom
- alkyl group preferably an alkyl group having 1 to 30 carbon atoms
- alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
- alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably an aryl group having 6 to 30 carbon atoms
- a heterocyclic group preferably a heterocyclic group having 1 to 30 carbon atoms
- an amino group preferably an amino group having 0 to 30 carbon atoms
- an alkoxy group preferably an alkoxy group having 1 to 30 carbon atoms
- an aryloxy group preferably an aryloxy group having 6 to 30 carbon atoms
- a heterocyclic oxy group preferably a carbon Heterocyclic oxy group having 1 to 30 carbon atoms
- Specific examples of the specific compound include compounds having the structures shown below. Resonance structures of these compounds are also mentioned as specific examples of specific compounds.
- the maximum absorption wavelength of the specific compound is preferably in the wavelength range of 650 to 1,500 nm, more preferably in the wavelength range of 680 to 1,200 nm, and even more preferably in the wavelength range of 700 to 1,000 nm.
- the composition of the present invention can contain an infrared absorber (another infrared absorber) other than the specific compound mentioned above. Furthermore, by containing other infrared absorbers, it is possible to form a film that can block infrared rays in a wider wavelength range.
- Other infrared absorbers may be dyes or pigments (particles).
- infrared absorbers include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, polymethine compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, and triarylmethane compounds. , pyrromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like.
- Examples of pyrrolopyrrole compounds include compounds described in paragraph numbers 0016 to 0058 of JP2009-263614A, compounds described in paragraphs 0037 to 0052 of JP2011-068731A, and compounds described in WO2015/166873A. Examples include compounds described in paragraph numbers 0010 to 0033. Examples of squarylium compounds include compounds described in paragraph numbers 0044 to 0049 of JP-A No. 2011-208101, compounds described in paragraph numbers 0060 to 0061 of Japanese Patent No. 6065169, and paragraph number 0040 of International Publication No. 2016/181987.
- Examples include the compounds described in paragraph numbers 0048 to 0063 of .
- Examples of phthalocyanine compounds include compounds described in paragraph number 0093 of JP-A No. 2012-077153, oxytitanium phthalocyanine described in JP-A 2006-343631, and paragraphs 0013 to 0029 of JP-A 2013-195480. , the vanadium phthalocyanine compound described in Patent No. 6081771, and the compound described in International Publication No. 2020/071470.
- Examples of naphthalocyanine compounds include compounds described in paragraph number 0093 of JP-A No. 2012-077153.
- Examples of the dithiolene metal complex include compounds described in Japanese Patent No. 5733804.
- metal oxide examples include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- metal borides include lanthanum boride.
- Commercially available lanthanum boride products include LaB 6 -F (manufactured by Nippon Shinkinzoku Co., Ltd.).
- a metal boride the compound described in International Publication No. 2017/119394 can also be used.
- commercially available indium tin oxide products include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- Linked squarylium compounds compounds having a pyrrole bis-type squarylium skeleton or croconium skeleton described in JP 2017-141215, dihydrocarbazole bis-type squarylium compounds described in JP 2017-082029, JP 2017-068120 Asymmetric compounds described in paragraph numbers 0027 to 0114 of the publication, pyrrole ring-containing compounds (carbazole type) described in JP 2017-067963, phthalocyanine compounds described in Patent No. 6251530, etc. are used. You can also do that.
- tungsten oxide represented by the following formula described in paragraph number 0025 of European Patent No. 3,628,645 can also be used.
- M 1 and M 2 represent ammonium cations or metal cations, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, and d is 2.5 to 3.
- e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent. represent.
- the content of the infrared absorber is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 3% by mass or more based on the total solid content of the composition. , 5% by mass or more is particularly preferred. Further, the upper limit of the content of the infrared absorber is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.
- the content of the above-mentioned specific compound is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and still more preferably 3% by mass or more based on the total solid content of the composition. The content is preferably 5% by mass or more, particularly preferably 5% by mass or more.
- the upper limit of the content of the specific compound mentioned above is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.
- the composition of the present invention may contain only one type of specific compound, or may contain two or more types of specific compounds. When two or more types are included, it is preferable that their total amount falls within the above range.
- the content of the other infrared absorbers is preferably 1 to 1000 parts by mass, and 3 to 500 parts by mass based on 100 parts by mass of the above-mentioned specific compound. It is more preferably 5 to 300 parts by weight, and even more preferably 5 to 300 parts by weight.
- the composition of the present invention may contain only one type of other infrared absorber, or may contain two or more types of other infrared absorbers. When two or more types are included, it is preferable that their total amount falls within the above range.
- the composition of the invention contains a curable compound.
- the curable compound include polymerizable compounds, resins, and the like.
- the resin may be a non-polymerizable resin (resin that does not have a polymerizable group) or a polymerizable resin (resin that has a polymerizable group).
- the polymerizable group include an ethylenically unsaturated bond-containing group, a cyclic ether group, a methylol group, and an alkoxymethyl group.
- Examples of the ethylenically unsaturated bond-containing group include a vinyl group, vinylphenyl group, (meth)allyl group, (meth)acryloyl group, (meth)acryloyloxy group, (meth)acryloylamide group, etc. Allyl group, (meth)acryloyl group and (meth)acryloyloxy group are preferred, and (meth)acryloyloxy group is more preferred.
- Examples of the cyclic ether group include an epoxy group and an oxetanyl group, with an epoxy group being preferred.
- the curable compound it is preferable to use one containing at least a resin.
- a resin and a polymerizable compound preferably a polymerizable monomer that is a monomer-type polymerizable compound
- the curable compound is preferable, and it is more preferable to use a resin and a polymerizable monomer (monomer type polymerizable compound) having an ethylenically unsaturated bond-containing group.
- polymerizable compound examples include a compound having an ethylenically unsaturated bond-containing group, a compound having a cyclic ether group, a compound having a methylol group, a compound having an alkoxymethyl group, and the like.
- a compound having an ethylenically unsaturated bond-containing group can be preferably used as a radically polymerizable compound.
- a compound having a cyclic ether group can be preferably used as a cationically polymerizable compound.
- resin-type polymerizable compounds include resins containing repeating units having polymerizable groups.
- the molecular weight of the monomer-type polymerizable compound is preferably less than 2,000, more preferably 1,500 or less.
- the lower limit of the molecular weight of the polymerizable monomer is preferably 100 or more, more preferably 200 or more.
- the weight average molecular weight (Mw) of the resin type polymerizable compound is preferably 2,000 to 2,000,000.
- the upper limit of the weight average molecular weight is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit of the weight average molecular weight is preferably 3,000 or more, more preferably 5,000 or more.
- the compound having an ethylenically unsaturated bond-containing group as a polymerizable monomer is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound.
- Specific examples include paragraph numbers 0095 to 0108 of JP 2009-288705, paragraph 0227 of JP 2013-029760, paragraph 0254 to 0257 of JP 2008-292970, and JP 2013-253224. Described in paragraph numbers 0034 to 0038 of the publication, paragraph number 0477 of JP 2012-208494, JP 2017-048367, JP 6057891, JP 6031807, JP 2017-194662. , the contents of which are incorporated herein.
- Examples of compounds having an ethylenically unsaturated bond-containing group include dipentaerythritol tri(meth)acrylate (commercially available product: KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available)
- Examples of commercially available products include KAYARAD D-320 (manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available products are KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), and dipentaerythritol hexa (meth) ) acrylate (commercially available products are KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.; NK ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), and the (meth)acryloyl group
- diglycerin EO (ethylene oxide) modified (meth)acrylate commercially available product is M-460; manufactured by Toagosei
- pentaerythritol tetraacrylate Shin Nakamura Chemical Co., Ltd.
- NK ester A-TMMT 1,6-hexanediol diacrylate
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 manufactured by Nippon Kayaku Co., Ltd.
- NK Oligo UA-7200 Shin Nakamura Chemical Co., Ltd.
- 8UH-1006, 8UH-1012 Taisei Fine Chemical Co., Ltd.
- examples of compounds having an ethylenically unsaturated bond-containing group include trimethylolpropane tri(meth)acrylate, trimethylolpropanepropylene oxide-modified tri(meth)acrylate, trimethylolpropaneethylene oxide-modified tri(meth)acrylate, and isocyanuric acid ethylene oxide. It is also preferable to use trifunctional (meth)acrylate compounds such as modified tri(meth)acrylate and pentaerythritol tri(meth)acrylate. Commercially available trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305.
- M-303, M-452, M-450 (manufactured by Toagosei Co., Ltd.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) Examples include.
- the compound having an ethylenically unsaturated bond-containing group may further have an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group.
- an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group.
- Commercially available products of such compounds include Aronix M-305, M-510, M-520, Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), and the like.
- a compound having a caprolactone structure can also be used.
- the description in paragraphs 0042 to 0045 of JP-A No. 2013-253224 can be referred to, the contents of which are incorporated herein.
- Examples of compounds having a caprolactone structure include DPCA-20, DPCA-30, DPCA-60, and DPCA-120, which are commercially available as a series from Nippon Kayaku Co., Ltd.
- a compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group can also be used.
- Such a compound is preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group and/or a propyleneoxy group, and preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group. More preferably, it is a 3- to 6-functional (meth)acrylate compound having 4 to 20 ethyleneoxy groups.
- SR-494 a tetrafunctional (meth)acrylate having four ethyleneoxy groups manufactured by Sartomer, and trifunctional (meth)acrylate having three isobutyleneoxy groups manufactured by Nippon Kayaku Co., Ltd.
- examples include KAYARAD TPA-330.
- a polymerizable compound having a fluorene skeleton can also be used.
- Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
- the compound having an ethylenically unsaturated bond-containing group it is also preferable to use a compound substantially free of environmentally regulated substances such as toluene.
- Commercially available products of such compounds include KAYARAD DPHA LT, KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.), and the like.
- Examples of the compound having a cyclic ether group include a compound having an epoxy group, a compound having an oxetanyl group, etc., and a compound having an epoxy group is preferable.
- Examples of compounds having epoxy groups include compounds having 1 to 100 epoxy groups in one molecule.
- the upper limit of the number of epoxy groups can be, for example, 10 or less, or 5 or less.
- the lower limit of the number of epoxy groups is preferably 2 or more.
- the compound having a cyclic ether group may be a low molecular compound (for example, molecular weight less than 1000) or a macromolecule (for example, molecular weight 1000 or more, in the case of a polymer, the weight average molecular weight is 1000 or more).
- the weight average molecular weight of the cyclic ether group is preferably 200 to 100,000, more preferably 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
- Examples of compounds having a cyclic ether group include compounds described in paragraph numbers 0034 to 0036 of JP-A No. 2013-011869, compounds described in paragraph numbers 0147 to 0156 of JP-A-2014-043556, and JP-A No. 2014. Compounds described in paragraph numbers 0085 to 0092 of JP-A-089408 and compounds described in JP-A-2017-179172 can also be used.
- Examples of compounds having a methylol group include compounds in which a methylol group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- Examples of compounds having an alkoxymethyl group include compounds in which an alkoxymethyl group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- Compounds in which an alkoxymethyl group or a methylol group is bonded to a nitrogen atom include alkoxymethylated melamine, methylolated melamine, alkoxymethylated benzoguanamine, methylolated benzoguanamine, alkoxymethylated glycoluril, methylolated glycoluril, alkoxymethylated Preferred are urea and methylolated urea. Further, compounds described in paragraphs 0134 to 0147 of JP-A No. 2004-295116 and paragraphs 0095 to 0126 of JP-A No. 2014-089408 can also be used.
- the composition of the present invention can use a resin as a curable compound. It is preferable to use a curable compound containing at least a resin.
- the resin is blended, for example, for dispersing pigments and the like in the composition or for use as a binder.
- a resin used mainly for dispersing pigments and the like in a composition is also referred to as a dispersant.
- this use of the resin is just an example, and the resin can also be used for purposes other than this use.
- the resin having a polymerizable group also corresponds to a polymerizable compound.
- the weight average molecular weight of the resin is preferably 3,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, more preferably 5000 or more.
- resins include (meth)acrylic resin, epoxy resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, Examples include polyamide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, vinyl acetate resin, polyvinyl alcohol resin, polyvinyl acetal resin, polyurethane resin, and polyurea resin. One type of these resins may be used alone, or two or more types may be used in combination.
- norbornene resin is preferable from the viewpoint of improving heat resistance.
- Commercially available norbornene resins include, for example, the ARTON series manufactured by JSR Corporation (eg, ARTON F4520).
- the resins include the resin described in the examples of International Publication No. 2016/088645, the resin described in JP 2017-057265, the resin described in JP 2017-032685, and the resin described in JP 2017-032685.
- a resin having a fluorene skeleton can also be preferably used.
- the description in US Patent Application Publication No. 2017/0102610 can be referred to, the contents of which are incorporated herein.
- examples of the resin include resins described in paragraphs 0199 to 0233 of JP2020-186373A, alkali-soluble resins described in JP2020-186325A, and Korean Patent Publication No. 10-2020-0078339.
- the resin represented by Formula 1, the resin described in JP-A No. 2021-134350, can also be used.
- a resin having acid groups examples include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group. The number of these acid groups may be one, or two or more.
- a resin having an acid group can also be used as a dispersant.
- the acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g.
- the lower limit is preferably 50 mgKOH/g or more, more preferably 70 mgKOH/g or more.
- the upper limit is preferably 400 mgKOH/g or less, more preferably 200 mgKOH/g or less, even more preferably 150 mgKOH/g or less, and most preferably 120 mgKOH/g or less.
- a resin containing a repeating unit derived from a compound represented by formula (ED1) and/or a compound represented by formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer") is used. It is also preferable to include.
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A No. 2010-168539 can be referred to.
- paragraph number 0317 of JP-A-2013-029760 can be referred to, the contents of which are incorporated herein.
- the resin it is also preferable to use a resin having a polymerizable group.
- the polymerizable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, and more preferably an ethylenically unsaturated bond-containing group.
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0 to 15.
- the alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, even more preferably 1 to 3 carbon atoms, and particularly 2 or 3 carbon atoms.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3.
- Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
- Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- the resin contains a resin as a dispersant.
- the dispersant include acidic dispersants (acidic resins) and basic dispersants (basic resins).
- the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol % or more when the total amount of acid groups and basic groups is 100 mol %.
- the acid group that the acidic dispersant (acidic resin) has is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g.
- the basic dispersant refers to a resin in which the amount of basic groups is greater than the amount of acid groups.
- the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of acid groups and basic groups is 100 mol%.
- the basic group that the basic dispersant has is preferably an amino group.
- the resin used as a dispersant is a graft resin.
- the descriptions in paragraphs 0025 to 0094 of JP-A No. 2012-255128 can be referred to, the contents of which are incorporated herein.
- the resin used as a dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin has The basic nitrogen atom is not particularly limited as long as it exhibits basicity.
- the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
- the resin used as the dispersant has a structure in which a plurality of polymer chains are bonded to the core portion.
- resins include dendrimers (including star-shaped polymers).
- specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraph numbers 0196 to 0209 of JP-A No. 2013-043962.
- the resin used as a dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of the repeating unit having an ethylenically unsaturated bond-containing group in its side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and more preferably 20 to 70 mol% of the total repeating units of the resin. More preferably, it is mol%.
- resins described in JP 2018-087939, block copolymers (EB-1) to (EB-9) described in paragraph numbers 0219 to 0221 of Patent No. 6432077, Polyethyleneimine having a polyester side chain as described in International Publication No. 2016/104803, block copolymer as described in International Publication No. 2019/125940, block polymer having an acrylamide structural unit as described in JP-A No. 2020-066687 , a block polymer having an acrylamide structural unit described in JP-A No. 2020-066688, etc. can also be used.
- Dispersants are also available as commercial products, and specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Japan Lubrizol, the Efka series manufactured by BASF, and Ajinomoto Fine Techno Co., Ltd. Examples include the Ajisper series manufactured by Manufacturer. Further, the product described in paragraph number 0129 of JP 2012-137564A and the product described in paragraph number 0235 of JP 2017-194662A can also be used as a dispersant.
- the content of the curable compound is preferably 1 to 95% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, and particularly preferably 10% by mass or more.
- the upper limit is preferably 94% by mass or less, more preferably 90% by mass or less, even more preferably 85% by mass or less, and particularly preferably 80% by mass or less.
- the content of the polymerizable compound is preferably 1 to 85% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less.
- the content of the polymerizable monomer is preferably 1 to 50% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
- the content of the compound having an ethylenically unsaturated bond-containing group is 1 to 70% by mass in the total solid content of the composition. % is preferred.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 65% by mass or less, more preferably 60% by mass or less.
- the content of the compound having a cyclic ether group is preferably 1 to 95% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.
- the content of the resin is preferably 1 to 85% by mass based on the total solid content of the composition.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, and particularly preferably 10% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and particularly preferably 40% by mass or less.
- the content of the resin as a dispersant is preferably 0.1 to 40% by mass based on the total solid content of the composition.
- the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the content of the resin as a dispersant is preferably 1 to 100 parts by weight per 100 parts by weight of the pigment.
- the upper limit is preferably 80 parts by mass or less, more preferably 75 parts by mass or less.
- the lower limit is preferably 2.5 parts by mass or more, more preferably 5 parts by mass or more.
- composition of the present invention may contain only one type of curable compound, or may contain two or more types. When two or more types of curable compounds are included, the total amount thereof is preferably within the above range.
- the composition of the invention contains a solvent.
- the solvent include water and organic solvents, with organic solvents being preferred.
- the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents.
- paragraph number 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein.
- Ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can also be preferably used.
- organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
- aromatic hydrocarbons benzene, toluene, xylene, ethylbenzene, etc.
- organic solvents for environmental reasons (for example, 50 mass ppm (parts) based on the total amount of organic solvents). per million), 10 mass ppm or less, and 1 mass ppm or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content, and the metal content of the organic solvent is preferably 10 mass ppb (parts per billion) or less, for example. If necessary, an organic solvent at a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by Toyo Gosei Co., Ltd. (Kagaku Kogyo Nippo, November 13, 2015).
- Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the material of the filter is preferably polytetrafluoroethylene, polyethylene, or nylon.
- the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one type of isomer may be included, or multiple types may be included.
- the content of peroxide in the organic solvent is 0.8 mmol/L or less, and it is more preferable that the organic solvent contains substantially no peroxide.
- the content of the solvent in the composition is preferably 10 to 97% by mass.
- the lower limit is preferably 30% by mass or more, more preferably 40% by mass or more, even more preferably 50% by mass or more, even more preferably 60% by mass or more, and 70% by mass. It is particularly preferable that it is above.
- the upper limit is preferably 96% by mass or less, more preferably 95% by mass or less.
- the composition may contain only one kind of solvent, or may contain two or more kinds. When two or more types are included, it is preferable that their total amount falls within the above range.
- the composition of the present invention may further contain a dye derivative.
- Dye derivatives are used as dispersion aids.
- the dye derivative include compounds having a structure in which an acid group or a basic group is bonded to a dye skeleton.
- the pigment skeletons constituting the pigment derivative include squarylium pigment skeleton, pyrrolopyrrole pigment skeleton, diketopyrrolopyrrole pigment skeleton, quinacridone pigment skeleton, anthraquinone pigment skeleton, dianthraquinone pigment skeleton, benzisoindole pigment skeleton, and thiazine indigo pigment skeleton.
- examples include squarylium dye skeleton, pyrrolopyrrole dye skeleton, diketopyrrolopyrrole dye skeleton, phthalocyanine dye skeleton, quinacridone dye skeleton and benzimidazolone dye skeleton, and squarylium dye skeleton and pyrrolopyrrole dye skeleton are more preferable.
- Examples of the acid group include a carboxyl group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonamide group, an imide acid group, and salts thereof.
- Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ , etc.), ammonium ions, imidazolium ions, pyridinium ions, Examples include phosphonium ions.
- As the carboxylic acid amide group a group represented by -NHCOR A1 is preferable.
- a group represented by -NHSO 2 R A2 is preferable.
- the imide acid group is preferably a group represented by -SO 2 NHSO 2 R A3 , -CONHSO 2 R A4 , -CONHCOR A5 or -SO 2 NHCOR A6 , and -SO 2 NHSO 2 R A3 is more preferred.
- R A1 to R A6 each independently represent an alkyl group or an aryl group.
- the alkyl group and aryl group represented by R A1 to R A6 may have a substituent.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Examples of the basic group include an amino group, a pyridinyl group and its salts, an ammonium group salt, and a phthalimidomethyl group.
- Examples of atoms or atomic groups constituting the salt include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
- dye derivatives include compounds described in the Examples below.
- Compounds described in JP-A-10-195326, paragraph numbers 0086 to 0098 of International Publication No. 2011/024896, and paragraph numbers 0063 to 0094 of International Publication No. 2012/102399 are also included, and the contents of these are incorporated herein by reference. be incorporated into.
- the content of the pigment derivative is preferably 1 to 50 parts by weight based on 100 parts by weight of the pigment.
- the lower limit is preferably 3 parts by mass or more, more preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less. Only one type of dye derivative may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
- the composition of the present invention contains a polymerizable compound
- the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet to visible range are preferred.
- the photopolymerization initiator is preferably a radical photopolymerization initiator.
- photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and the like.
- halogenated hydrocarbon derivatives e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.
- acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and the like.
- photopolymerization initiators include trihalomethyltriazine compounds, benzyl dimethyl ketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, and hexaarylbylene compounds.
- imidazole compounds onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones
- the compound is more preferably a compound selected from a compound, an ⁇ -aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.
- photopolymerization initiators compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, compounds described in Japanese Patent No. 6301489, MATERIAL STAGE 37 to 60p, vol. 19, No.
- hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole, etc. can be mentioned.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, and Irgacure 1. 173, Irgacure 2959, Irgacure 127 (all BASF (manufactured by a company).
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, and Irgacure.
- acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (manufactured by BASF), and the like.
- Examples of oxime compounds include the compounds described in JP-A No. 2001-233842, the compounds described in JP-A No. 2000-080068, the compounds described in JP-A No. 2006-342166, and the compounds described in J. C. S. Perkin II (1979, pp. 1653-1660); C. S. Perkin II (1979, pp. 156-162), Journal of Photopolymer Science and Technology (1995, pp. 202-232), JP-A-2000 - Compounds described in Publication No. 066385, Compounds described in Japanese Patent Publication No. 2004-534797, compounds described in Japanese Patent Application Publication No. 2006-342166, compounds described in Japanese Patent Application Publication No. 2017-019766, compounds described in Japanese Patent No.
- oxime compounds include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like.
- an oxime compound having a fluorene ring can also be used.
- Specific examples of oxime compounds having a fluorene ring include the compounds described in JP-A No. 2014-137466, the compounds described in Japanese Patent No. 6636081, and the compounds described in Korean Patent Publication No. 10-2016-0109444. It will be done.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring is also possible.
- Specific examples of such oxime compounds include compounds described in International Publication No. 2013/083505.
- an oxime compound having a fluorine atom can also be used as a photopolymerization initiator.
- oxime compounds having a fluorine atom include compounds described in JP-A No. 2010-262028, compounds 24, 36 to 40 described in Japanese Patent Application Publication No. 2014-500852, and compounds described in JP-A No. 2013-164471. Examples include compound (C-3).
- an oxime compound having a nitro group can be used as the photopolymerization initiator. It is also preferable that the oxime compound having a nitro group is in the form of a dimer.
- Specific examples of oxime compounds having a nitro group include compounds described in paragraph numbers 0031 to 0047 of JP 2013-114249, paragraphs 0008 to 0012, and 0070 to 0079 of JP 2014-137466, Examples include compounds described in paragraph numbers 0007 to 0025 of Japanese Patent No. 4223071, and Adeka Arcles NCI-831 (manufactured by ADEKA Corporation).
- an oxime compound having a benzofuran skeleton can also be used.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- photopolymerization initiator it is also possible to use an oxime compound in which a substituent having a hydroxy group is bonded to a carbazole skeleton.
- photopolymerization initiators include compounds described in International Publication No. 2019/088055.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited thereto.
- the oxime compound is preferably a compound having a maximum absorption wavelength in a wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in a wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably from 1000 to 300,000, even more preferably from 2000 to 300,000, and even more preferably from 5000 to 200,000. It is particularly preferable that there be.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian) using an ethyl acetate solvent at a concentration of 0.01 g/L.
- a difunctional, trifunctional or more functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so that good sensitivity can be obtained.
- the crystallinity decreases and the solubility in solvents and the like improves, making it difficult to precipitate over time, thereby improving the stability of the composition over time.
- Specific examples of bifunctional or trifunctional or more functional photoradical polymerization initiators include those listed in Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
- the content of the photopolymerization initiator is preferably 0.1 to 40% by weight, more preferably 0.5 to 35% by weight, and even more preferably 1 to 30% by weight based on the total solid content of the composition.
- the composition may contain only one type of photopolymerization initiator, or may contain two or more types of photopolymerization initiators. When two or more types are included, it is preferable that their total amount falls within the above range.
- the composition of the present invention contains a compound having a cyclic ether group
- the composition further contains a curing agent.
- the curing agent include amine compounds, acid anhydride compounds, amide compounds, phenol compounds, polyhydric carboxylic acids, and thiol compounds.
- Specific examples of the curing agent include succinic acid, trimellitic acid, pyromellitic acid, N,N-dimethyl-4-aminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), and the like.
- the curing agent compounds described in paragraph numbers 0072 to 0078 of JP-A No. 2016-075720 and compounds described in JP-A No.
- the content of the curing agent is preferably 0.01 to 20 parts by weight, more preferably 0.01 to 10 parts by weight, and 0.1 to 6.0 parts by weight per 100 parts by weight of the compound having a cyclic ether group. is even more preferable.
- compositions of the invention can contain chromatic colorants.
- a chromatic colorant means a colorant other than a white colorant and a black colorant.
- the chromatic colorant is preferably a colorant having absorption in a wavelength range of 400 nm or more and less than 650 nm.
- Chromatic colorants include red colorants, green colorants, blue colorants, yellow colorants, purple colorants, and orange colorants.
- the chromatic colorant may be a pigment or a dye.
- a pigment and a dye may be used together.
- the pigment may be either an inorganic pigment or an organic pigment.
- an inorganic pigment or an organic-inorganic pigment partially substituted with an organic chromophore can also be used. By replacing inorganic pigments or organic-inorganic pigments with organic chromophores, hue design can be facilitated.
- the average primary particle diameter of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
- the average primary particle diameter of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment using a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circular equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle diameter in the present invention is the arithmetic mean value of the primary particle diameters of 400 pigment primary particles.
- the primary particles of pigment refer to independent particles without agglomeration.
- the chromatic colorant preferably contains a pigment.
- the content of pigment in the chromatic colorant is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 90% by mass or more. It is particularly preferable. Examples of pigments include those shown below.
- red pigments C. I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64 (phthalocyanine type), 65 (phthalocyanine type), 66 (phthalocyanine type), etc.
- green pigments C. I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60 (triarylmethane type), 61 (xanthene type), etc.
- purple pigments C. I. Pigment Blue 1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,29,60,64,66,79,80,87 (monoazo type), 88 (methine type), etc. (the above are blue pigments).
- halogenated zinc phthalocyanine pigments have an average number of halogen atoms in one molecule of 10 to 14, an average number of bromine atoms of 8 to 12, and an average of 2 to 5 chlorine atoms. You can also use Specific examples include compounds described in International Publication No. 2015/118720.
- a green pigment a compound described in Chinese Patent Application No. 106909027, a phthalocyanine compound having a phosphoric acid ester as a ligand described in International Publication No. 2012/102395, a phthalocyanine compound described in JP-A No.
- a phthalocyanine compound a phthalocyanine compound described in JP 2018-180023, a compound described in JP 2019-038958, a core-shell type dye described in JP 2020-076995, etc. can also be used.
- an aluminum phthalocyanine compound having a phosphorus atom can also be used as the blue pigment.
- Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A No. 2012-247591 and paragraph number 0047 of JP-A No. 2011-157478.
- JP 2018-062644 The quinophthalone compound described in JP 2018-203798, the quinophthalone compound described in JP 2018-062578, and Japanese Patent No. 6432076.
- red pigment As a red pigment, a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP 2017-201384, a diketopyrrolopyrrole compound described in paragraph numbers 0016 to 0022 of Patent No. 6248838, Diketopyrrolopyrrole compounds described in International Publication No. 2012/102399, diketopyrrolopyrrole compounds described in International Publication No. 2012/117965, naphthol azo compounds described in JP2012-229344A, Patent No. 6516119 Red pigment described in the publication, red pigment described in Patent No.
- the descriptions in Japanese Patent No. 6561862, Japanese Patent No. 6413872, Japanese Patent No. 6281345, and Japanese Patent Application Laid-open No. 2020-026503 can be referred to. Incorporated herein.
- the crystallite size in the plane direction corresponding to the maximum peak in the X-ray diffraction pattern among the eight planes ( ⁇ 1 ⁇ 1 ⁇ 1) of the crystal lattice planes is 140 ⁇ or less. It is also preferable to use one.
- Dyes can also be used as chromatic colorants. There are no particular restrictions on the dye, and any known dye can be used. For example, pyrazole azo dyes, anilinoazo dyes, triarylmethane dyes, anthraquinone dyes, anthrapyridone dyes, benzylidene dyes, oxonol dyes, pyrazolotriazole azo dyes, pyridone azo dyes, cyanine dyes, and phenothiazines. Examples include pyrrolopyrazole azomethine dyes, xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, pyrromethene dyes, and the like.
- Pigment multimers can also be used as chromatic colorants.
- the dye multimer is preferably a dye that is dissolved in a solvent. Further, the dye multimer may form particles. When the dye multimer is in the form of particles, it is usually used in a state of being dispersed in a solvent.
- the dye multimer in a particle state can be obtained, for example, by emulsion polymerization, and specific examples include the compound and manufacturing method described in JP-A No. 2015-214682.
- the dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less.
- the plurality of dye structures contained in one molecule may be the same dye structure or may be different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
- the lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more.
- the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
- Dye multimers are described in JP 2011-213925, JP 2013-041097, JP 2015-028144, JP 2015-030742, WO 2016/031442, etc. Compounds can also be used.
- chromatic colorants include thiazole compounds described in JP-A No. 2012-158649, azo compounds described in JP-A No. 2011-184493, azo compounds described in JP-A No. 2011-145540, and azo compounds described in JP-A No. 2011-145540.
- Triarylmethane dye polymer described in Patent No. 10-2020-0028160, xanthene compound described in JP 2020-117638, phthalocyanine compound described in WO 2020/174991, JP 2020-160279 The isoindoline compounds or salts thereof described in the above publication can be used.
- the content of the chromatic colorant is preferably 1 to 50% by mass based on the total solid content of the composition of the present invention.
- the total amount thereof is preferably within the above range.
- the composition of the present invention does not substantially contain a chromatic colorant.
- the content of the chromatic colorant in the total solid content of the composition of the present invention is 0.5% by mass or less. This means that it is preferably 0.1% by mass or less, and more preferably does not contain a chromatic colorant.
- the composition of the present invention can also contain a coloring material that transmits infrared rays and blocks visible light (hereinafter also referred to as a coloring material that blocks visible light).
- a composition containing a coloring material that blocks visible light is preferably used as a composition for forming an infrared transmission filter.
- the coloring material that blocks visible light is preferably a coloring material that absorbs light in the wavelength range from violet to red. Further, the coloring material that blocks visible light is preferably a coloring material that blocks light in a wavelength range of 450 to 650 nm. Further, the coloring material that blocks visible light is preferably a coloring material that transmits light with a wavelength of 900 to 1500 nm.
- the coloring material that blocks visible light preferably satisfies at least one of the following requirements (A) and (B).
- B Contains an organic black colorant.
- Examples of the chromatic colorant include those mentioned above.
- Examples of the organic black colorant include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred.
- Examples of bisbenzofuranone compounds include compounds described in Japanese Patent Application Publication No. 2010-534726, Japanese Patent Application Publication No. 2012-515233, and Japanese Patent Application Publication No. 2012-515234, and for example, as "Irgaphor Black" manufactured by BASF. available.
- Examples of perylene compounds include compounds described in paragraph numbers 0016 to 0020 of JP-A No. 2017-226821, C.I. I. Pigment Black 31, 32, etc.
- Examples of the azomethine compound include compounds described in JP-A-01-170601 and JP-A-02-034664, and are available as "Chromofine Black A1103" manufactured by Dainichiseika Kaisha, Ltd., for example.
- examples of the combination of chromatic colorants include the following embodiments (1) to (8).
- An embodiment containing a green colorant, a blue colorant, a purple colorant, and a red colorant An embodiment containing a green colorant, a blue colorant, a purple colorant, and a red colorant.
- Embodiment containing a purple colorant and an orange colorant Embodiment containing a green colorant, a purple colorant, and a red colorant.
- Embodiment containing a green colorant and a red colorant Embodiment containing a green colorant and a red colorant.
- the content of the colorant that blocks visible light is preferably 1 to 50% by mass based on the total solid content of the composition.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and particularly preferably 30% by mass or more.
- the composition of the present invention does not substantially contain a coloring material that blocks visible light.
- a coloring material that blocks visible light means that the content of the colorant that blocks visible light in the total solid content of the composition of the present invention is 0. This means 5% by mass or less, preferably 0.1% by mass or less, and more preferably no coloring material that blocks visible light.
- the composition of the invention contains a surfactant.
- a surfactant various surfactants such as fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used.
- the surfactant is preferably a silicone surfactant or a fluorine surfactant. Examples of the surfactant include the surfactants described in paragraph numbers 0238 to 0245 of International Publication No. 2015/166779, the contents of which are incorporated herein.
- fluorine-based surfactants examples include surfactants described in paragraph numbers 0060 to 0064 of JP 2014-041318 (corresponding paragraph numbers 0060 to 0064 of WO 2014/017669), and the like; Examples include the surfactants described in paragraph numbers 0117 to 0132 of Publication No. 132503 and the surfactants described in JP-A-2020-008634, the contents of which are incorporated herein.
- Commercially available fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144.
- fluorine-based surfactants there are also acrylic compounds that have a molecular structure with a functional group containing a fluorine atom, and when heated, the functional group containing a fluorine atom is cut off and the fluorine atom volatizes. It can be used suitably.
- fluorine-based surfactants include the Megafac DS series manufactured by DIC Corporation (Kagaku Kogyo Nippo (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), An example is DS-21.
- fluorinated surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorinated surfactant.
- fluorine-based surfactants include the fluorine-based surfactants described in JP-A No. 2016-216602, the content of which is incorporated herein.
- a block polymer can also be used as the fluorosurfactant.
- a fluorine-based surfactant a (meth) having a repeating unit derived from a (meth)acrylate compound having a fluorine atom and two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy group, propyleneoxy group)
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the fluorine-containing surfactants described in paragraph numbers 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-containing surfactant used in the present invention.
- the weight average molecular weight of the above compound is preferably 3,000 to 50,000, for example 14,000. In the above compounds, % indicating the proportion of repeating units is mol%.
- a fluoropolymer having an ethylenically unsaturated bond-containing group in its side chain can also be used as the fluorinated surfactant.
- Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A No. 2010-164965, Megafac RS-101, RS-102, RS-718K manufactured by DIC Corporation, Examples include RS-72-K.
- the fluorine-based surfactant compounds described in paragraph numbers 0015 to 0158 of JP-A No. 2015-117327 can also be used.
- a fluorine-containing imide salt compound represented by formula (fi-1) is also preferable to use as a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a+ represents an a-valent metal ion, a primary ammonium ion
- a Re represents a secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH 4 + .
- nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Japan Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (manufactured by Japan
- cationic surfactant examples include tetraalkylammonium salts, alkylamine salts, benzalkonium salts, alkylpyridium salts, imidazolium salts, and the like. Specific examples include dihydroxyethylstearylamine, 2-heptadecenyl-hydroxyethylimidazoline, lauryldimethylbenzylammonium chloride, cetylpyridinium chloride, stearamidemethylpyridium chloride, and the like.
- Anionic surfactants include dodecylbenzenesulfonic acid, sodium dodecylbenzenesulfonate, sodium lauryl sulfate, sodium alkyldiphenyl ether disulfonate, sodium alkylnaphthalenesulfonate, sodium dialkylsulfosuccinate, sodium stearate, potassium oleate, sodium dioctyl Sulfosuccinate, sodium polyoxyethylene alkyl ether sulfate, sodium polyoxyethylene alkyl ether sulfate, sodium polyoxyethylene alkyl phenyl ether sulfate, sodium dialkyl sulfosuccinate, sodium stearate, sodium oleate, t-octylphenoxyethoxypolyethoxyethyl Examples include sodium sulfate salt.
- silicone surfactants examples include SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), TSF-4440, TSF-4300 , TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-3760, BYK-UV3510 (manufactured by BYK-Chemie Co., Ltd.), and the like.
- a compound having the following structure can also be used as the silicone surfactant.
- the content of the surfactant is preferably 0.001 to 1% by mass, more preferably 0.001 to 0.5% by mass, and even more preferably 0.001 to 0.2% by mass based on the total solid content of the composition.
- the composition may contain only one kind of surfactant, or may contain two or more kinds of surfactants. When two or more types are included, it is preferable that their total amount falls within the above range.
- the composition of the present invention may contain a polymerization inhibitor.
- Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), Examples include 2,2'-methylenebis(4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.), with p-methoxyphenol being preferred.
- the content of the polymerization inhibitor is preferably 0.0001 to 5% by mass based on the total solid content of the composition.
- the composition may contain only one kind of polymerization inhibitor, or may contain two or more kinds of polymerization inhibitors. When two or more types are included, it is preferable that their total amount falls within the above range.
- the composition of the present invention may contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the term "hydrolyzable group" refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, and an alkoxy group is preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of functional groups other than hydrolyzable groups include vinyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, ureido groups, sulfide groups, isocyanate groups, and phenyl groups. (meth)acryloyl group and epoxy group are preferred.
- Examples of the silane coupling agent include compounds described in paragraph numbers 0018 to 0036 of JP-A No. 2009-288703 and compounds described in paragraph numbers 0056 to 0066 of JP-A No. 2009-242604, the contents of which are incorporated herein by reference. Incorporated into the specification.
- the content of the silane coupling agent is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass based on the total solid content of the composition.
- the composition may contain only one type of silane coupling agent, or may contain two or more types. When two or more types are included, it is preferable that their total amount falls within the above range.
- the composition of the present invention can contain a UV absorber.
- the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, dibenzoyl compounds, and the like. Specific examples of such compounds include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraphs 0052 to 0072 of JP2012-208374A, and paragraphs 0317 to 0317 of JP2013-068814A.
- UV absorbers include the Tinuvin series and Uvinul series manufactured by BASF.
- examples of the benzotriazole compound include the MYUA series manufactured by Miyoshi Yushi (Kagaku Kogyo Nippo, February 1, 2016).
- the ultraviolet absorber compounds described in the Examples described later, paragraph numbers 0049 to 0059 of Patent No. 6268967, and compounds described in paragraph numbers 0059 to 0076 of International Publication No.
- the content of the ultraviolet absorber is preferably 0.01 to 30% by mass, more preferably 0.05 to 25% by mass based on the total solid content of the composition.
- the composition may contain only one type of ultraviolet absorber, or may contain two or more types. When two or more types are included, it is preferable that their total amount falls within the above range.
- compositions of the invention may contain antioxidants.
- the antioxidant include phenolic antioxidants, amine antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like.
- examples of phenolic antioxidants include hindered phenol compounds.
- the phenolic antioxidant is preferably a compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position).
- the above-mentioned substituents are preferably substituted or unsubstituted alkyl groups having 1 to 22 carbon atoms.
- the antioxidant is a compound having a phenol group and a phosphite group in the same molecule.
- antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330, ADEKA STAB AO-412S, ADEKA STAB 2112, ADEKA STAB PEP-36, ADEKA STAB HP-10 (manufactured by ADEKA Co., Ltd.), and JP-650 (manufactured by Johoku Kagaku Kogyo Co., Ltd.).
- the antioxidants include compounds described in paragraph numbers 0023 to 0048 of Patent No.
- the content of the antioxidant is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass based on the total solid content of the composition.
- the composition may contain only one kind of antioxidant, or may contain two or more kinds. When two or more types are included, it is preferable that their total amount falls within the above range.
- composition of the present invention may optionally contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers, and other auxiliary agents (e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, etc.). agent, peeling accelerator, fragrance, surface tension regulator, chain transfer agent, etc.).
- sensitizers curing accelerators
- fillers thermosetting accelerators
- plasticizers plasticizers
- auxiliary agents e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, etc.
- agent peeling accelerator
- fragrance surface tension regulator
- chain transfer agent etc.
- the composition of the present invention may also contain a latent antioxidant, if necessary.
- a latent antioxidant is a compound whose moiety that functions as an antioxidant is protected with a protecting group, and is heated at 100 to 250°C or heated at 80 to 200°C in the presence of an acid/base catalyst. Examples include compounds that function as antioxidants by removing protective groups. Examples of the latent antioxidant include compounds described in WO 2014/021023, WO 2017/030005, and JP 2017-008219. Commercially available latent antioxidants include Adeka Arcles GPA-5001 (manufactured by ADEKA Co., Ltd.).
- the container for storing the composition of the present invention is not particularly limited, and any known container can be used.
- any known container in order to prevent impurities from entering raw materials and compositions, we use multi-layer bottles with an inner wall made of 6 types of 6 layers of resin, and bottles with 7 layers of 6 types of resin as storage containers. It is also preferable to use Examples of such a container include the container described in JP-A No. 2015-123351.
- the inner wall of the container is preferably made of glass, stainless steel, or the like for the purpose of preventing metal elution from the inner wall of the container, increasing stability of the composition over time, and suppressing deterioration of components.
- composition of the present invention can be prepared by mixing the components described above.
- the composition may be prepared by dissolving or dispersing all the components in a solvent at the same time, or if necessary, two or more solutions or dispersions containing each component may be prepared in advance.
- the composition may be prepared by mixing these at the time of use (at the time of application).
- the preparation of the composition may include a process of dispersing the pigment.
- mechanical forces used for dispersing pigments include compression, squeezing, impact, shearing, cavitation, and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion, and the like.
- pulverizing pigments in a sand mill (bead mill) it is preferable to use small-diameter beads or increase the filling rate of the beads, thereby increasing the pulverizing efficiency.
- the process and dispersion machine for dispersing pigments are described in ⁇ Complete Works of Dispersion Technology, Published by Information Technology Corporation, July 15, 2005'' and ⁇ Dispersion technology centered on suspension (solid/liquid dispersion system) and industrial
- the process and dispersion machine described in Paragraph No. 0022 of JP 2015-157893 A, "Practical Application Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be suitably used.
- the pigment may be subjected to a finer treatment in a salt milling step. For the materials, equipment, processing conditions, etc.
- Bead materials used for dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, and glass.
- an inorganic compound having a Mohs hardness of 2 or more can also be used for the beads.
- the composition may contain 1 to 10,000 ppm of the beads.
- any filter that has been conventionally used for filtration and the like can be used without particular limitation.
- fluororesins such as polytetrafluoroethylene (PTFE), polyamide resins such as nylon (e.g. nylon-6, nylon-6,6), polyolefin resins (high density, ultra-high molecular weight) such as polyethylene, polypropylene (PP), etc.
- PTFE polytetrafluoroethylene
- nylon e.g. nylon-6, nylon-6,6)
- polyolefin resins high density, ultra-high molecular weight
- polyethylene polypropylene
- PP polypropylene
- filters using materials such as polyolefin resin (including polyolefin resin).
- polypropylene (including high-density polypropylene) and nylon are preferred.
- the pore diameter of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the pore size value of the filter reference can be made to the nominal value of the filter manufacturer.
- various filters provided by Nippon Pole Co., Ltd. DFA4201NXEY, DFA4201NAEY, DFA4201J006P, etc.
- Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), Kitz Microfilter Co., Ltd., etc. can be used. .
- fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers.
- Commercially available products include the SBP type series (SBP008, etc.), the TPR type series (TPR002, TPR005, etc.), and the SHPX type series (SHPX003, etc.) manufactured by Loki Techno.
- filters When using filters, different filters (for example, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed two or more times. Further, filters having different pore diameters within the above-mentioned range may be combined. Alternatively, only the dispersion liquid may be filtered with the first filter, and then filtered with the second filter after other components are mixed.
- filters for example, a first filter and a second filter, etc.
- the membrane of the present invention is obtained from the composition of the present invention described above.
- the film of the present invention can be preferably used as an optical filter.
- Applications of the optical filter are not particularly limited, but include infrared cut filters, infrared transmission filters, and the like.
- Examples of the infrared cut filter include an infrared cut filter on the light receiving side of the solid-state image sensor (for example, an infrared cut filter for a wafer level lens, etc.), and an infrared cut filter on the back side of the solid-state image sensor (opposite side to the light receiving side).
- infrared cut filters for environmental light sensors (for example, illuminance sensors that detect the illuminance and color tone of the environment in which the information terminal device is placed and adjust the color tone of the display, and color correction sensors that adjust the color tone). It will be done. In particular, it can be preferably used as an infrared cut filter on the light receiving side of a solid-state image sensor. Examples of the infrared transmission filter include a filter that can block visible light and selectively transmit infrared rays having a specific wavelength or more.
- the film of the present invention may have a pattern or may be a film without a pattern (flat film). Further, the membrane of the present invention may be used by being laminated on a support, or the membrane of the present invention may be used by being peeled off from the support. Examples of the support include semiconductor base materials such as silicon substrates and transparent base materials.
- a charge coupled device (CCD), complementary metal oxide semiconductor (CMOS), transparent conductive film, etc. may be formed on the semiconductor substrate used as the support. Further, a black matrix may be formed on the semiconductor substrate to isolate each pixel. Further, an undercoat layer may be provided on the semiconductor substrate, if necessary, for improving adhesion with the upper layer, preventing substance diffusion, or flattening the substrate surface.
- CCD charge coupled device
- CMOS complementary metal oxide semiconductor
- transparent conductive film etc.
- a black matrix may be formed on the semiconductor substrate to isolate each pixel.
- an undercoat layer may be provided on the semiconductor substrate, if necessary, for improving adhesion with the upper layer, preventing substance diffusion, or flattening the substrate surface.
- the transparent substrate used as the support is not particularly limited as long as it is made of a material that can transmit at least visible light.
- Examples include base materials made of materials such as glass and resin.
- resins include polyester resins such as polyethylene terephthalate and polybutylene terephthalate, polyolefin resins such as polyethylene, polypropylene, and ethylene vinyl acetate copolymers, acrylic resins such as norbornene resins, polyacrylates, and polymethyl methacrylates, urethane resins, and vinyl chloride resins. , fluororesin, polycarbonate resin, polyvinyl butyral resin, polyvinyl alcohol resin, and the like.
- glass examples include soda lime glass, borosilicate glass, alkali-free glass, quartz glass, and glass containing copper.
- glass containing copper examples include phosphate glass containing copper, fluorophosphate glass containing copper, and the like.
- a commercially available glass containing copper can also be used. Examples of commercially available glass containing copper include NF-50 (manufactured by AGC Techno Glass Co., Ltd.).
- the thickness of the film of the present invention can be adjusted as appropriate depending on the purpose.
- the thickness of the film can be 200 ⁇ m or less, 150 ⁇ m or less, 120 ⁇ m or less, 20 ⁇ m or less, 10 ⁇ m or less, and 5 ⁇ m or less. You can also do it.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more.
- the film of the present invention When the film of the present invention is used as an infrared cut filter, it is preferable that the film of the present invention has a maximum absorption wavelength in a wavelength range of 650 to 1500 nm (preferably a wavelength of 660 to 1200 nm, more preferably a wavelength of 660 to 1000 nm).
- the average transmittance of light with a wavelength of 420 to 550 nm is preferably 50% or more, more preferably 70% or more, even more preferably 80% or more, and especially 85% or more.
- the transmittance over the entire wavelength range of 420 to 550 nm is preferably 50% or more, more preferably 70% or more, and even more preferably 80% or more.
- the film of the present invention preferably has a transmittance of 15% or less at at least one point in the wavelength range of 650 to 1500 nm (preferably wavelength 660 to 1200 nm, more preferably wavelength 660 to 1000 nm), and preferably 10% or less.
- the content is more preferably 5% or less, and even more preferably 5% or less.
- the film of the present invention preferably has an average absorbance of less than 0.030, more preferably less than 0.025, in the wavelength range of 420 to 550 nm, when the absorbance at the maximum absorption wavelength is 1.
- the film of the present invention preferably has, for example, any one of the following spectral properties (i1) to (i3).
- a film having such spectral characteristics can block light in a wavelength range of 400 to 850 nm and transmit light with a wavelength exceeding 950 nm.
- the maximum value of transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1100 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength exceeding 1050 nm.
- the maximum value of transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1200 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 1050 nm and transmit light with a wavelength exceeding 1150 nm.
- the film of the present invention can also be used in combination with a color filter containing a chromatic colorant.
- a color filter can be manufactured using a coloring composition containing a chromatic colorant.
- the color filter is preferably disposed on the optical path of the film of the present invention.
- the film of the present invention may be formed on a support different from the support on which the color filter is formed, and the film of the present invention may be formed on a support different from the support on which the color filter is formed.
- Other members for example, microlenses, flattening layers, etc. constituting the solid-state imaging device may be interposed between the film and the color filter.
- the film of the present invention can be used in various devices such as solid-state imaging devices such as CCDs (charge-coupled devices) and CMOSs (complementary metal oxide semiconductors), infrared sensors, and image display devices.
- solid-state imaging devices such as CCDs (charge-coupled devices) and CMOSs (complementary metal oxide semiconductors)
- infrared sensors and image display devices.
- the membrane of the present invention can be manufactured through a step of applying the composition of the present invention.
- Examples of the support include those mentioned above.
- a method for applying the composition a known method can be used. For example, drop casting method; slit coating method; spray method; roll coating method; spin coating method; casting coating method; slit and spin method; Various methods such as inkjet (for example, on-demand method, piezo method, thermal method), ejection printing such as nozzle jet, flexo printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc. Examples include printing method; transfer method using a mold etc.; nanoimprint method.
- the application method for inkjet is not particularly limited, and for example, the method shown in "Expanding and Usable Inkjet - Infinite Possibilities Seen in Patents," Published February 2005, Sumibe Techno Research (especially from page 115). 133 pages), and methods described in JP-A No. 2003-262716, JP-A No. 2003-185831, JP-A No. 2003-261827, JP-A No. 2012-126830, JP-A No. 2006-169325, etc. Can be mentioned.
- the composition layer formed by applying the composition may be dried (prebaked).
- the prebaking temperature is preferably 150°C or lower, more preferably 120°C or lower, and even more preferably 110°C or lower.
- the lower limit can be, for example, 50°C or higher, or 80°C or higher.
- the prebake time is preferably 10 seconds to 3000 seconds, more preferably 40 to 2500 seconds, and even more preferably 80 to 220 seconds. Drying can be performed using a hot plate, oven, or the like.
- the film manufacturing method may further include a step of forming a pattern.
- the pattern forming method include a pattern forming method using a photolithography method and a pattern forming method using a dry etching method, and a pattern forming method using a photolithography method is preferable. Note that when the film of the present invention is used as a flat film, the step of forming a pattern may not be performed. Hereinafter, the process of forming a pattern will be explained in detail.
- the pattern forming method using the photolithography method includes a step of exposing a composition layer formed by applying the composition of the present invention to light in a pattern (exposure step), and developing and removing the unexposed portions of the composition layer. It is preferable to include a step of forming a pattern (developing step). If necessary, a step of baking the developed pattern (post-bake step) may be provided. Each step will be explained below.
- the composition layer is exposed in a pattern.
- the composition layer can be exposed in a pattern by exposing the composition layer to light through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. This allows the exposed portion to be cured.
- Radiation (light) that can be used during exposure includes g-line, i-line, etc. Furthermore, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm), ArF rays (wavelength 193 nm), and KrF rays (wavelength 248 nm). Furthermore, a long-wave light source of 300 nm or more can also be used.
- pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and pauses in short cycles (for example, on the millisecond level or less).
- the irradiation amount is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to being carried out in the atmosphere, for example, in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially
- the exposure may be performed in an oxygen-free environment (in the absence of oxygen), or in a high oxygen atmosphere with an oxygen concentration of more than 21 volume % (for example, 22 volume %, 30 volume %, or 50 volume %).
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000W/m 2 to 100000W/m 2 (for example, 5000W/m 2 , 15000W/m 2 , or 35000W/m 2 ). I can do it.
- the oxygen concentration and the exposure illuminance may be appropriately combined.
- the illumination intensity may be 10,000 W/m 2 at an oxygen concentration of 10% by volume, or 20,000 W/m 2 at an oxygen concentration of 35% by volume.
- the unexposed portions of the composition layer after exposure are removed by development to form a pattern.
- the composition layer in the unexposed area can be removed by development using a developer.
- the temperature of the developer is preferably, for example, 20 to 30°C.
- the development time is preferably 20 to 180 seconds.
- the process of shaking off the developer every 60 seconds and supplying a new developer may be repeated several times.
- Examples of the developer include organic solvents, alkaline developers, and alkaline developers are preferably used.
- an alkaline aqueous solution (alkaline developer) prepared by diluting an alkaline agent with pure water is preferable.
- alkaline agents include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- alkaline compounds examples include alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium silicate, and sodium metasilicate.
- alkali agent compounds with a large molecular weight are preferable from the environmental and safety standpoints.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the surfactant nonionic surfactants are preferred.
- the developing solution may be manufactured as a concentrated solution and then diluted to a required concentration before use.
- the dilution ratio is not particularly limited, but can be set, for example, in the range of 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Further, rinsing is preferably performed by supplying a rinsing liquid to the developed composition layer while rotating the support on which the developed composition layer is formed.
- the nozzle that discharges the rinsing liquid from the center of the support it is also preferable to move the nozzle that discharges the rinsing liquid from the center of the support to the peripheral edge of the support.
- the nozzle may be moved while gradually decreasing its moving speed.
- Additional exposure processing and post-bake are post-development curing processing to complete curing.
- the heating temperature in post-baking is, for example, preferably 100 to 240°C, more preferably 200 to 240°C.
- Post-baking can be carried out in a continuous or batch manner using a heating means such as a hot plate, convection oven (hot air circulation dryer), or high-frequency heater to maintain the developed film under the above conditions.
- the light used for exposure is preferably light with a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by the dry etching method involves applying the above composition onto a support and curing the composition layer to form a cured product layer, and then forming a patterned photoresist layer on this cured product layer. This can be carried out by forming a patterned photoresist layer as a mask, and dry etching the cured material layer using an etching gas. In forming the photoresist layer, it is preferable to perform a prebaking process. Regarding pattern formation by the dry etching method, the descriptions in paragraphs 0010 to 0067 of JP-A No. 2013-064993 can be referred to, and the contents thereof are incorporated into the present specification.
- optical filter of the present invention has the film of the present invention described above.
- Types of optical filters include infrared cut filters and infrared transmission filters.
- the optical filter of the invention may further include a copper-containing layer, a dielectric multilayer film, an ultraviolet absorbing layer, and the like.
- the ultraviolet absorbing layer include the absorbing layers described in paragraph numbers 0040 to 0070 and 0119 to 0145 of International Publication No. 2015/099060.
- the dielectric multilayer film include the dielectric multilayer films described in paragraph numbers 0255 to 0259 of JP-A No. 2014-041318.
- a glass substrate made of glass containing copper (copper-containing glass substrate) or a layer containing a copper complex (copper complex-containing layer) can also be used.
- Examples of the copper-containing glass substrate include phosphate glass containing copper, fluorophosphate glass containing copper, and the like.
- Commercially available copper-containing glasses include NF-50 (manufactured by AGC Techno Glass Co., Ltd.), BG-60, BG-61 (all manufactured by Schott Co., Ltd.), and CD5000 (manufactured by HOYA Co., Ltd.).
- the solid-state imaging device of the present invention includes the film of the present invention described above.
- the structure of the solid-state image sensor is not particularly limited as long as it has the film of the present invention and functions as a solid-state image sensor. For example, the following configurations may be mentioned.
- the device On the support, there is a transfer electrode made of polysilicon or the like and a plurality of photodiodes that constitute the light-receiving area of the solid-state image sensor, and a light-shielding material made of tungsten or the like with only the light-receiving part of the photodiode opened above the photodiode and the transfer electrode.
- the device has a device protective film made of silicon nitride or the like formed to cover the entire surface of the light shielding film and the photodiode light receiving part on the light shielding film, and has the film of the present invention on the device protective film. be.
- the color filter may have a structure in which a film forming each pixel is embedded in a space partitioned into, for example, a lattice shape by partition walls.
- the partition wall preferably has a lower refractive index than each pixel. Examples of imaging devices having such a structure include devices described in Japanese Patent Application Laid-open Nos. 2012-227478 and 2014-179577.
- the image display device of the present invention includes the film of the present invention.
- Examples of the image display device include a liquid crystal display device and an organic electroluminescence (organic EL) display device.
- organic EL organic electroluminescence
- image display devices see, for example, “Electronic Display Devices (written by Akio Sasaki, published by Industrial Research Institute Co., Ltd., 1990)” and “Display Devices (written by Junaki Ibuki, published by Sangyo Tosho Co., Ltd., published in 1989). Publication)” etc.
- liquid crystal display devices are described, for example, in “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosenkai Co., Ltd., published in 1994)”.
- the image display device may include a white organic EL element.
- the white organic EL element preferably has a tandem structure.
- Japanese Patent Application Laid-open No. 2003-045676 supervised by Akiyoshi Mikami, "The forefront of organic EL technology development - High brightness, high precision, long life, collection of know-how", Technical Information Association, It is described in pages 326-328, 2008, etc.
- the spectrum of white light emitted by the organic EL element preferably has strong maximum emission peaks in the blue region (430 to 485 nm), green region (530 to 580 nm), and yellow region (580 to 620 nm). In addition to these emission peaks, it is more preferable to have a maximum emission peak in the red region (650 to 700 nm).
- the infrared sensor of the present invention includes the film of the present invention described above.
- the configuration of the infrared sensor is not particularly limited as long as it functions as an infrared sensor. EMBODIMENT OF THE INVENTION Hereinafter, one embodiment of the infrared sensor of this invention is described using drawings.
- numeral 110 is a solid-state image sensor.
- An infrared cut filter 111 and an infrared transmission filter 114 are arranged on the imaging area of the solid-state image sensor 110.
- a color filter 112 is arranged on the infrared cut filter 111.
- a microlens 115 is arranged on the incident light hv side of the color filter 112 and the infrared transmission filter 114.
- a flattening layer 116 is formed to cover the microlens 115.
- the infrared cut filter 111 can be formed using the composition of the present invention.
- the color filter 112 is a color filter in which pixels that transmit and absorb light of a specific wavelength in the visible region are formed, and there is no particular limitation, and a conventionally known color filter for forming pixels can be used. For example, a color filter in which red (R), green (G), and blue (B) pixels are formed is used. For example, the descriptions in paragraph numbers 0214 to 0263 of JP-A No. 2014-043556 can be referred to, and the contents thereof are incorporated herein.
- the characteristics of the infrared transmission filter 114 are selected depending on the emission wavelength of the infrared LED used.
- the infrared transmission filter 114 can be formed using the composition of the present invention.
- an infrared cut filter other than the infrared cut filter 111 may be further disposed on the flattening layer 116.
- Other infrared cut filters include those having a layer containing copper and/or a dielectric multilayer film. Details of these are mentioned above.
- a dual band pass filter may be used as another infrared cut filter.
- the camera module of the present invention includes a solid-state image sensor and the above-described film of the present invention.
- the camera module further includes a lens and a circuit that processes images obtained from the solid-state image sensor.
- the solid-state image sensor used in the camera module may be the solid-state image sensor according to the present disclosure described above, or may be a known solid-state image sensor.
- the lens used in the camera module and the circuit that processes the image obtained from the solid-state image sensor known ones can be used.
- camera modules described in JP-A No. 2016-006476 and JP-A No. 2014-197190 can be referred to, and the contents thereof are incorporated into this specification.
- Intermediate 1 was synthesized by the method described in US Patent Application Publication No. 2014/0061505.
- Intermediate 2 was synthesized by the method described in International Publication No. 2011/107501.
- Intermediate 3 was synthesized by the method described in International Publication No. 2014/088063.
- Intermediate 4 was synthesized by the method described in Bioconjugate Chemistry (2017), 28(5), 1552-1559.
- Intermediate 5 is described in Organic and Biomolecular Chemistry, 2011, vol. 9, #23, p8122-8129.
- Intermediate 5 (4.4 g, 7.0 mmol) and squaric acid (0.36 g, 3.1 mmol) were heated under reflux for 12 hours in n-butanol/toluene (26 mL/60 mL) with azeotropic dehydration.
- composition ⁇ Manufacture of composition> The components listed in the table below were mixed in the parts by mass listed in the table below, stirred, and then filtered through a nylon filter (manufactured by Nippon Pall Co., Ltd.) with a pore size of 0.45 ⁇ m to produce a composition. .
- B-a-1 to B-a-3 Compounds with the following structure (phthalocyanine compounds) B-b-1 to B-b-8: Compounds with the following structure (pentamethine compounds) B-c-1 to B-c-3: Compounds with the following structure (squarylium compounds) B-d-1 to B-d-3: Compounds with the following structure (heptamethine compounds) B-d-4: Compound with the following structure (cyanine compound) B-e-1: Compound with the following structure (iminium compound)
- (resin) C-1 Resin with the following structure synthesized by the method described in Resin Synthesis Example 1 of JP 2021-134350 A (weight average molecular weight 137,000, number average molecular weight 32,000, glass transition temperature 165 ° C.)
- C-2 Resin with the following structure synthesized by the method described in Resin Synthesis Example 2 of JP 2021-134350 A (weight average molecular weight 188,000, number average molecular weight 75,000, glass transition temperature 285 ° C.)
- C-3 Resin with the following structure synthesized by the method described in Resin Synthesis Example 3 of JP-A-2021-134350 (The numerical value appended to the main chain represents the molar ratio of the repeating unit. Glass transition temperature 310 ° C.
- C-4 Acryviewer (manufactured by Nippon Shokubai Co., Ltd., acrylic resin)
- C-5 Resin with the following structure (the numbers appended to the main chain represent the mass ratio of repeating units. Weight average molecular weight 26100, number average molecular weight 8600, epoxy equivalent 355 g/eq, acid value 163 mg KOH/g, glass transition temperature 133 °C)
- C-6 Resin with the following structure (the numbers appended to the main chain represent the mass ratio of repeating units.
- C-8 Resin with the following structure (the numbers appended to the main chain represent the mass ratio of repeating units.
- Weight average molecular weight 9500, number average molecular weight 5800) C-11 Resin with the following structure (the numbers appended to the main chain represent the mass ratio of repeating units.
- C-12 EPICLON N-695 (manufactured by DIC Corporation, novolac type epoxy resin)
- C-13 Resin with the following structure (the numbers appended to the main chain represent the molar ratio of repeating units.
- C-14 Resin with the following structure (the numbers appended to the main chain represent the weight ratio of repeating units.
- Weight average molecular weight 9700, number average molecular weight 5700, acid value 130 mgKOH/g) C-15 Resin with the following structure (the numbers appended to the main chain represent the weight ratio of repeating units.
- Weight average molecular weight 15100, number average molecular weight 7000, acid value 136 mgKOH/g) C-16 Resin with the following structure (the numbers appended to the main chain represent the weight ratio of repeating units.
- Weight average molecular weight 17000, number average molecular weight 7700, acid value 32 mgKOH/g) C-17 Resin with the following structure (the numbers appended to the main chain represent the weight ratio of repeating units.
- D-1 Compound with the following structure (maximum absorption wavelength in dichloromethane: 394 nm)
- D-2 Uvinul3050 (manufactured by BASF, compound with the following structure)
- D-3 Tinuvin477 (manufactured by BASF, hydroxyphenyltriazine-based ultraviolet absorber)
- D-4 Tinuvin326 (manufactured by BASF, compound with the following structure)
- D-5 Compound (2)-22 described in International Publication No. 2021/131355 (compound with the following structure)
- D-6 Compound (1)-46 described in International Publication No.
- D-7 Compound A-1 (compound with the following structure) described in International Publication No. 2021/132247
- D-8 NeoHeliopan357 (manufactured by Symrise, compound with the following structure)
- D-9 Compound with the following structure
- E-1 ADEKA STAB AO-60 (manufactured by ADEKA Co., Ltd., compound with the following structure)
- E-2 ADEKA STAB AO-80 (manufactured by ADEKA Co., Ltd., compound with the following structure)
- E-3 Compound with the following structure
- E-4 ADEKA STAB 2112 (manufactured by ADEKA Co., Ltd., compound with the following structure)
- E-5 ADEKA STAB PEP-36 (manufactured by ADEKA Co., Ltd., compound with the following structure)
- E-6 ADEKA STAB HP-10 (manufactured by ADEKA Co., Ltd., compound with the following structure)
- E-7 ADEKA STAB AO-412S (manufactured by ADEKA Co., Ltd., compound with the following structure)
- G-1 FTX-218D (manufactured by Neos, fluorine-based surfactant)
- G-2 Megafac F-554 (manufactured by DIC Corporation, fluorine-based surfactant)
- G-3 KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant)
- G-4 Compound with the following structure (weight average molecular weight 14,000, the numerical value of % indicating the proportion of repeating units is mol%)
- H-1 Trimellitic acid
- H-2 2-ethyl-4-methylimidazole
- H-3 Methyltetrahydrophthalic anhydride
- J-1 Irgacure OXE01 (manufactured by BASF, oxime ester compound)
- J-2 Compound No. described in International Publication No. 2017/169819. 1 (compound with the following structure)
- J-3 Compound No. described in International Publication No. 2017/169819. 10
- J-4 Compound No. described in JP-A No. 2019-168654. 5 (compound with the following structure)
- J-5 Compound No. described in JP-A No. 2019-168654. 73 (compound with the following structure)
- A Average transmittance in the wavelength range of 700 nm to 720 nm ⁇ 2%
- B 2% ⁇ average transmittance in the wavelength range of 700 nm to 720 nm ⁇ 4%
- C 4% ⁇ average transmittance in the wavelength range of 700 nm to 720 nm ⁇ 7%
- D 7% ⁇ average transmittance in the wavelength range of 700 nm to 720 nm ⁇ 10%
- E 10% ⁇ average transmittance in the wavelength range of 700 nm to 720 nm
- the average transmittance of the obtained film in the wavelength range of 420 to 550 nm was measured using a spectrophotometer U-4100 (manufactured by Hitachi High-Tech Corporation), and the visible light transmittance was evaluated according to the following criteria.
- A Average transmittance in the wavelength range of 420 nm to 550 nm ⁇ 95%
- B 92% ⁇ average transmittance in the wavelength range of 420 nm to 550 nm ⁇ 95%
- C 89% ⁇ average transmittance in the wavelength range of 420 nm to 550 nm ⁇ 92%
- D 86% ⁇ average transmittance in the wavelength range of 420 nm to 550 nm ⁇ 89%
- E Average transmittance in the wavelength range of 420 nm to 550 nm ⁇ 86%
- the obtained film was subjected to a light resistance test by irradiating it with 50,000 lux light for 20 hours through a UV cut filter using a Xe lamp, and was tested using a color meter MCPD-1000 (manufactured by Otsuka Electronics Co., Ltd.).
- the ⁇ Eab value of the color difference before and after irradiation was measured. A smaller ⁇ Eab value indicates better light resistance.
- the ⁇ Eab value is a value obtained from the following color difference formula based on the CIE1976 (L*, a*, b*) space color system (edited by the Color Society of Japan, New Edition Color Science Handbook (1985) p. 266) .
- ⁇ Eab ⁇ ( ⁇ L*) 2 + ( ⁇ a*) 2 + ( ⁇ b*) 2 ⁇ 1/2
- the examples were better than the comparative examples in terms of visible light transmittance, infrared shielding properties, light resistance, and storage stability.
- 110 solid-state image sensor
- 111 infrared cut filter
- 112 color filter
- 114 infrared transmission filter
- 115 microlens
- 116 flattening layer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
Abstract
Cette composition comprend un agent absorbant les infrarouges, un composé durcissable et un solvant, l'agent absorbant les infrarouges comprenant un composé représenté par la formule (1). L'invention concerne un film, un filtre optique, un élément d'imagerie à semi-conducteurs, un dispositif d'affichage d'image, un capteur infrarouge, un module de caméra et un composé.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020247028586A KR20240144253A (ko) | 2022-03-18 | 2023-03-08 | 조성물, 막, 광학 필터, 고체 촬상 소자, 화상 표시 장치, 적외선 센서, 카메라 모듈 및 화합물 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2022044340 | 2022-03-18 | ||
JP2022-044340 | 2022-03-18 |
Publications (1)
Publication Number | Publication Date |
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WO2023176609A1 true WO2023176609A1 (fr) | 2023-09-21 |
Family
ID=88023254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2023/008715 WO2023176609A1 (fr) | 2022-03-18 | 2023-03-08 | Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, capteur infrarouge, module de caméra et composé |
Country Status (3)
Country | Link |
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KR (1) | KR20240144253A (fr) |
TW (1) | TW202342649A (fr) |
WO (1) | WO2023176609A1 (fr) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01314250A (ja) * | 1988-06-13 | 1989-12-19 | Konica Corp | 電子写真感光体 |
JPH0213964A (ja) * | 1988-07-01 | 1990-01-18 | Konica Corp | 電子写真感光体 |
WO2013054864A1 (fr) * | 2011-10-14 | 2013-04-18 | Jsr株式会社 | Filtre optique, dispositif de capture d'image à l'état solide utilisant celui-ci et module de caméra utilisant celui-ci |
WO2014088063A1 (fr) * | 2012-12-06 | 2014-06-12 | 旭硝子株式会社 | Filtre de blocage du proche infrarouge |
KR101842495B1 (ko) * | 2017-03-13 | 2018-03-27 | 한국화학연구원 | 스쿠아릴륨 화합물, 이를 포함하는 근적외선 흡수용 수지 조성물 및 이를 이용하여 제조된 근적외선 차단필터 |
WO2021039205A1 (fr) * | 2019-08-29 | 2021-03-04 | 富士フイルム株式会社 | Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé |
-
2023
- 2023-03-08 WO PCT/JP2023/008715 patent/WO2023176609A1/fr unknown
- 2023-03-08 KR KR1020247028586A patent/KR20240144253A/ko unknown
- 2023-03-14 TW TW112109380A patent/TW202342649A/zh unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01314250A (ja) * | 1988-06-13 | 1989-12-19 | Konica Corp | 電子写真感光体 |
JPH0213964A (ja) * | 1988-07-01 | 1990-01-18 | Konica Corp | 電子写真感光体 |
WO2013054864A1 (fr) * | 2011-10-14 | 2013-04-18 | Jsr株式会社 | Filtre optique, dispositif de capture d'image à l'état solide utilisant celui-ci et module de caméra utilisant celui-ci |
WO2014088063A1 (fr) * | 2012-12-06 | 2014-06-12 | 旭硝子株式会社 | Filtre de blocage du proche infrarouge |
KR101842495B1 (ko) * | 2017-03-13 | 2018-03-27 | 한국화학연구원 | 스쿠아릴륨 화합물, 이를 포함하는 근적외선 흡수용 수지 조성물 및 이를 이용하여 제조된 근적외선 차단필터 |
WO2021039205A1 (fr) * | 2019-08-29 | 2021-03-04 | 富士フイルム株式会社 | Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé |
Also Published As
Publication number | Publication date |
---|---|
TW202342649A (zh) | 2023-11-01 |
KR20240144253A (ko) | 2024-10-02 |
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