WO2022168741A1 - Colored composition, film, optical filter, solid imaging element, image display device, and compound - Google Patents
Colored composition, film, optical filter, solid imaging element, image display device, and compound Download PDFInfo
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- WO2022168741A1 WO2022168741A1 PCT/JP2022/003236 JP2022003236W WO2022168741A1 WO 2022168741 A1 WO2022168741 A1 WO 2022168741A1 JP 2022003236 W JP2022003236 W JP 2022003236W WO 2022168741 A1 WO2022168741 A1 WO 2022168741A1
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- CVDUUPMTIHXQKC-UHFFFAOYSA-N ethene 1,3,5-triazinane-2,4,6-trione Chemical group C=C.O=C1NC(=O)NC(=O)N1 CVDUUPMTIHXQKC-UHFFFAOYSA-N 0.000 description 1
- WSTZPWUPYWHZRR-UHFFFAOYSA-N ethene;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical group C=C.CCC(CO)(CO)CO WSTZPWUPYWHZRR-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- YDMWUMUNUXUYKT-UHFFFAOYSA-N ethyl [(1-oxo-1-phenylpropan-2-ylidene)amino] carbonate Chemical compound CCOC(=O)ON=C(C)C(=O)C1=CC=CC=C1 YDMWUMUNUXUYKT-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- KVFVBPYVNUCWJX-UHFFFAOYSA-M ethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](C)(C)C KVFVBPYVNUCWJX-UHFFFAOYSA-M 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-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
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 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
- 125000005395 methacrylic acid group Chemical group 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-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
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 238000007645 offset printing Methods 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
- 239000001061 orange colorant Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000008520 organization Effects 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
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 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
- 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
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 150000008301 phosphite esters Chemical group 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
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006350 polyacrylonitrile resin Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 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
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 230000002250 progressing effect Effects 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
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical group N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- GGVMPKQSTZIOIU-UHFFFAOYSA-N quaterrylene Chemical group C12=C3C4=CC=C2C(C2=C56)=CC=C5C(C=57)=CC=CC7=CC=CC=5C6=CC=C2C1=CC=C3C1=CC=CC2=CC=CC4=C21 GGVMPKQSTZIOIU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 150000003852 triazoles Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Definitions
- the present invention relates to a coloring composition containing a coloring agent.
- the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device using the colored composition.
- the present invention also relates to azomethine metal complex compounds.
- a color filter usually comprises three primary color pixels of red, green and blue and serves to separate the transmitted light into the three primary colors.
- Patent Document 1 discloses a pigment composition for color filters containing a phthalocyanine-based pigment and an azomethine copper complex-based pigment, wherein the mass ratio of the phthalocyanine-based pigment to the azomethine copper complex-based pigment is 99.9/ A color filter pigment composition is described which is from 0.1 to 96.5/3.5.
- C.I. Pigment Yellow 129 is used as an azomethine copper complex-based pigment.
- C. I. Pigment Yellow 129 is a compound having the structure shown below. According to the study of the present inventor, the film obtained using the composition containing the azomethine copper complex-based pigment described in the examples of Patent Document 1 cannot be said to have sufficient light resistance, and there is room for improvement. It turns out there is.
- a coloring composition containing a coloring agent and a resin A coloring composition in which the coloring agent contains a compound Y in which a compound represented by formula (1) is coordinated to a metal atom;
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- X 2 to X 9 each independently represents a nitrogen atom, CH or CR x
- R x represents a substituent
- Adjacent two of X 6 to X 9 in formula (1) are CR x , and R x of two adjacent CR x are bonded to form a ring, ⁇ 1 >
- the coloring composition described in . ⁇ 3> The colored composition according to ⁇ 1> or ⁇ 2>, wherein at least one of X 2 to X 9 in formula (1) is CR x , and R x is a heteroatom-containing group.
- At least one of X 2 to X 9 in formula (1) is CR x , and R x is a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 , —COOR 105 , —OCOR 106 , —SO 2 R 107 , —SO 2 NR 108 R 109 , —SO 2 OR 110 , —CONR 111 R 112 or —NR 113 COR 114 , wherein R 101 and R 102 each independently represent , represents a hydrogen atom, an alkyl group or an aryl group, R 101 and R 102 may combine to form a ring, R 103 to R 114 each independently represent an alkyl group or an aryl group, The colored composition according to any one of ⁇ 1> to ⁇ 3>.
- ⁇ 9> The colored composition according to any one of ⁇ 1> to ⁇ 8>, further comprising a polymerizable compound and a photopolymerization initiator.
- ⁇ 10> The colored composition according to any one of ⁇ 1> to ⁇ 9>, which is used for color filters or infrared transmission filters.
- ⁇ 11> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 12> An optical filter comprising the film according to ⁇ 11>.
- ⁇ 13> A solid-state imaging device comprising the film according to ⁇ 11>.
- ⁇ 14> An image display device comprising the film according to ⁇ 11>.
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- X 2 to X 9 each independently represents a nitrogen atom, CH or CR x
- R x represents a substituent
- formula (1) satisfies any of the following requirements 1 to 4
- Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring
- Requirement 2 X 2 and X 3 are CR x
- R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring
- Requirement 3 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring
- Requirement 2 X 2 and X 3 are CR
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- (meth)acrylate represents both or either acrylate and methacrylate
- (meth)acryl represents both or either acrylic and methacrylic
- (meth) ) acryloyl refers to acryloyl and/or methacryloyl.
- the coloring composition of the present invention is a coloring composition containing a coloring agent and a resin,
- the coloring agent is characterized by containing a compound Y in which a compound represented by formula (1) is coordinated to a metal atom.
- the coloring composition of the present invention a film with excellent light resistance can be formed. Although the detailed reason why such an effect is obtained is unknown, it is presumed to be due to the following.
- Compound Y used as a colorant in the coloring composition of the present invention is easy to form an association in the film, also, since it is possible to efficiently transfer electrons between molecules, the coloring composition of the present invention It is presumed that a film with excellent light resistance could be formed by using
- the coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters. More specifically, it can be preferably used as a coloring composition for forming color filter pixels or as a coloring composition for forming infrared transmission filters, and is more preferably used as a coloring composition for forming color filter pixels.
- Pixel types include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Red pixels, green pixels, and yellow pixels are preferred. More preferably, it is a green pixel.
- the wavelength at which the light transmittance of the film is 50% is preferably present in the wavelength range of 470 to 520 nm. More preferably in the wavelength range of 520 nm, even more preferably in the wavelength range of 480-520 nm. In particular, it is preferable that the wavelengths at which the light transmittance is 50% exist in both the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the wavelength on the short wavelength side at which the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm.
- the number of carbon atoms in the alkyl group represented by R 1 in formula (1) is preferably 1-30, more preferably 1-15, and even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent.
- Substituents include the substituent T described later.
- the aryl group represented by R 1 in formula (1) preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent.
- Substituents include the substituent T described later.
- R 1 in formula (1) is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
- Specific functional groups A include a nitro group, a cyano group, -NR 101 R 102 , -OR 103 , -SR 104 , -COOR 105 , -OCOR 106 , -SO 2 R 107 , -SO 2 NR 108 R 109 , - SO 2 OR 110 , —CONR 111 R 112 and —NR 113 COR 114 , preferably a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 and —COOR 105 , — NR 101 R 102 and -OR 103 are more preferred.
- R 101 and R 102 each independently represent a hydrogen atom, an alkyl group or an aryl group, R 101 and R 102 may combine to form a ring, and R 103 to R 114 each independently , represents an alkyl group or an aryl group.
- the R x 's of the two adjacent CR x 's may combine to form a ring.
- the ring to be formed may be a hydrocarbon ring or a hetero ring.
- the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring.
- Heteroatoms contained in the heterocycle include nitrogen, sulfur and oxygen atoms.
- the heterocycle is preferably a 5- or 6-membered ring.
- Formula (1) satisfies any one of requirements 1 to 4 above.
- At least one of X 6 to X 9 is CR x and R x is a heteroatom-containing group (preferably, the specific functional group A described above).
- Requirement 2 is that X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring.
- Examples of the heterocycle formed by combining R x include the heterocycles described above.
- the hetero ring formed by combining R x may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- At least one of X 6 to X 9 is CR x and R x is a heteroatom-containing group (preferably the above-mentioned specific functional group A).
- Requirement 3 is that adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring.
- the ring formed by combining R x include the rings described above, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the ring formed by combining R x may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- X 6 and X 7 are each independently CR x , and R x of CR x represented by X 6 and R x of CR x represented by X 7 can be formed. are combined to form a ring, or X 7 and X 8 are each independently CR x , and R x of CR x represented by X 7 and R x of CR x represented by X 8 are preferably bonded to form a ring, X 7 and X 8 are each independently CR x , and R x of CR x represented by X 7 and R of CR x represented by X 8 It is more preferable that x is bonded to form a ring.
- Formula (1) preferably satisfies any one of requirements 1, 3 or 4 described above, more preferably satisfies requirement 3 or requirement 4, and satisfies requirement 3 More preferred.
- the compound represented by formula (1) is preferably a compound represented by formula (1-1).
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 9 each independently represent a hydrogen atom or a substituent, adjacent two of R 2 to R 9 may combine to form a ring
- formula (1-1) satisfies any of the following requirements 1a to 4a; Requirement 1a adjacent two of R 3 to R 5 are bonded to form a ring; Requirement 2a R 2 and R 3 are combined to form a heterocycle; Requirement 3a adjacent two of R 6 to R 9 are bonded to form a ring; Requirement 4a At least one of R 2 and R 3 is a hydrogen atom, and at least one of R 2 to R 9 is a substituent.
- R 1 in formula (1-1) has the same definition as R 1 in formula (1).
- Substituents represented by R 2 to R 9 in formula (1-1) include the substituent T described later, preferably a group containing a heteroatom, more preferably the specific functional group A described above. preferable.
- adjacent two of R 2 to R 9 may combine to form a ring.
- the ring to be formed includes the rings described above.
- the ring thus formed may further have a substituent.
- Substituents include the substituent T described later.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- Requirement 1a is that adjacent two of R 3 to R 5 are bonded to form a ring.
- the ring to be formed includes the rings described above, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the ring formed above may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- Requirement 3a is that adjacent two of R 6 to R 9 are bonded to form a ring.
- the ring to be formed includes the rings described above, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the ring formed above may further have a substituent.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- Requirement 4a is that at least one of R 2 and R 3 is a hydrogen atom, and at least one of R 2 to R 9 is a substituent.
- 1 to 4 of R 2 to R 9 are preferably substituents, more preferably 1 or 2 are substituents.
- Substituents include the substituent T described below.
- the substituent is preferably a group containing a heteroatom, more preferably the specific functional group A described above.
- the metal atoms coordinated by the compound represented by formula (1) include copper atom, zinc atom, iron atom, titanium atom, aluminum atom, tin atom, magnesium atom, chromium atom, calcium atom and silicon atom. Atoms can be mentioned, preferably a copper atom and a zinc atom, more preferably a copper atom.
- one compound represented by formula (1) may be coordinated to the metal atom, or two or more compounds may be coordinated. Further, the metal atom may be further coordinated with a ligand other than the compound represented by formula (1).
- a red colorant a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, a diketopyrrolopyrrole described in paragraphs 0016 to 0022 of Japanese Patent No.
- green colorants include C.I. I. Green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66 are included. Further, as a green colorant, a halogenated zinc phthalocyanine having an average number of halogen atoms of 10 to 14, an average number of bromine atoms of 8 to 12, and an average number of chlorine atoms of 2 to 5 per molecule. Pigments can also be used. Specific examples include compounds described in International Publication No. 2015/118720. In addition, as a green colorant, the compound described in Chinese Patent Application No.
- C.I. I. Pigment Green 7, 36, 58, 62 and 63 are preferred, C.I. I. Pigment Greens 36 and 58 are more preferred.
- chromatic colorants triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP-A-2020-117638, and International Publication No. 2020/174991.
- the phthalocyanine compound described, the isoindoline compound described in JP-A-2020-160279, or a salt thereof can be used.
- the coloring composition of the present invention contains a green coloring agent, it is preferably used as a coloring composition for forming green pixels of color filters. Moreover, when the coloring composition of the present invention contains a red coloring agent, it is preferably used as a coloring composition for forming red pixels of a color filter.
- the coloring composition of the present invention contains a resin.
- the resin is blended, for example, for dispersing a pigment or the like in a coloring composition or as a binder.
- a resin mainly used for dispersing a pigment or the like in a coloring composition is also called a dispersant.
- such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
- the acid value of the resin having acid groups is preferably 30-500 mgKOH/g.
- the lower limit is more preferably 40 mgKOH/g or more, particularly preferably 50 mgKOH/g or more.
- the upper limit is more preferably 400 mgKOH/g or less, still more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less.
- the weight average molecular weight (Mw) of the acid group-containing resin is preferably 5,000 to 100,000, more preferably 5,000 to 50,000.
- the number average molecular weight (Mn) of the resin having an acid group is preferably 1,000 to 20,000.
- 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 cyclic ether group is preferably at least one selected from the group represented by the formula (e-1) and the group represented by the formula (e-2), and the group represented by the formula (e-2) It is more preferable that the group is When n in formula (e-1) is 0, the group represented by formula (e-1) is an epoxy group, and when n is 1, it is represented by formula (e-1) The group is an oxetanyl group. Also, the group represented by formula (e-2) is an alicyclic epoxy group.
- X a1 represents a trivalent linking group
- L a1 represents a single bond or a divalent linking group
- Z a1 represents a cyclic ether group.
- Examples of the trivalent linking group represented by X a1 in the formula (A1) include a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, and a polyamide linking group.
- Linking groups, polyether-based linking groups, polystyrene-based linking groups, bisphenol-based linking groups, novolac-based linking groups, etc. poly(meth)acrylic-based linking groups, polyether-based linking groups, polyester-based linking groups, bisphenol-based linking groups, etc.
- a linking group and a novolac linking group are preferred, a polyether linking group, a novolak linking group and a poly(meth)acrylic linking group are more preferred, and a poly(meth)acrylic linking group is even more preferred.
- the content of repeating units having a cyclic ether group in the resin having a cyclic ether group is preferably 1 to 100 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 90 mol % or less, more preferably 80 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- the resin having a cyclic ether group may have other repeating units in addition to the repeating unit having a cyclic ether group.
- Other repeating units include a repeating unit having an acid group (hereinafter also referred to as repeating unit B-1) and a repeating unit having a group in which the acid group is protected with a protecting group (hereinafter also referred to as repeating unit B-2). , a repeating unit having an ethylenically unsaturated bond-containing group (hereinafter also referred to as repeating unit B-3).
- Examples of the protecting group for protecting the acid group in the repeating unit B-2 include groups that are decomposed and eliminated by the action of an acid or base.
- the protecting group is preferably a group represented by any one of formulas (Y1) to (Y5), and is a group represented by formula (Y3) or formula (Y5) because it is easy to deprotect. is more preferred.
- R Y1 to R Y3 each independently represent an alkyl group, and two of R Y1 to R Y3 may combine to form a ring;
- R Y4 to R Y6 each independently represent an alkyl group, and two of R Y4 to R Y6 may combine to form a ring;
- R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl group.
- the number of carbon atoms in the alkyl groups represented by R Y1 to R Y3 in formula (Y1) is preferably 1 to 12, more preferably 1 to 6, even more preferably 1 to 4.
- the alkyl group may be linear, branched, or cyclic, but preferably linear or branched. In formula (Y1), two of R Y1 to R Y3 may combine to form a ring.
- R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring.
- Alkyl groups may be linear, branched, or cyclic.
- the number of carbon atoms in the alkyl group is preferably 1-12, more preferably 1-6, even more preferably 1-4.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
- the molecular weight of the protective group is preferably 40-200, more preferably 40-150, even more preferably 40-120. If the molecular weight of the protective group is within the above range, a colored composition having excellent storage stability and excellent curability at low temperatures can be obtained.
- Examples of the ethylenically unsaturated bond-containing group possessed by the repeating unit B-3 include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- Examples of the group in which the acid group represented by Z b2 of the formula (B2) is protected by a protecting group include groups in which the acid group is protected by a group represented by any one of the formulas (Y1) to (Y5) described above. It is preferable that the acid group is a group protected by a group represented by formula (Y3) or formula (Y5).
- Examples of the acid group include a phenolic hydroxy group, a carboxyl group, a sulfo group and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxyl group, more preferably a carboxyl group.
- Examples of the ethylenically unsaturated bond-containing group represented by Zb3 in formula (B3) include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- the content of the unit B-3 in the resin having a cyclic ether group is 1 to 65 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 45 mol % or less, more preferably 30 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- aromatic carboxy group-containing group represented by Ar 1 in formula (Ac-1) examples include structures derived from aromatic tricarboxylic acid anhydrides, structures derived from aromatic tetracarboxylic acid anhydrides, and the like.
- Aromatic tricarboxylic anhydrides and aromatic tetracarboxylic anhydrides include compounds having the following structures.
- the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
- L 2a is an alkylene group; an arylene group; a group in which an alkylene group and an arylene group are combined; at least one selected from an alkylene group and an arylene group; Examples include groups in which at least one selected from —NH— and —S— are combined, and alkylene groups are preferred.
- the number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, and even more preferably 1-15.
- the alkylene group may be linear, branched or cyclic. An alkylene group and an arylene group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- L 12c represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( The binding position of Ac- 2 ) with P10 is shown.
- the trivalent linking group represented by L 12c includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, preferably a hydrocarbon group.
- the resin used as the dispersant is also preferably a polyimine-based dispersant containing nitrogen atoms in at least one of its main chain and side chains.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and at least one of the main chain and the side chain has a basic nitrogen atom.
- a resin having The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting 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 is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of repeating units having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, more preferably 20 to 70, of the total repeating units of the resin. More preferably, it is mol %.
- the coloring composition of the present invention preferably contains a polymerizable compound.
- the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
- ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- E is each independently -((CH 2 ) y CH 2 O)- or -((CH 2 ) y CH(CH 3 )O)- , y each independently represents an integer of 0 to 10, and each X independently represents a (meth)acryloyl group, a hydrogen atom, or a carboxy group.
- the total number of (meth)acryloyl groups is 3 or 4
- the sum of m is an integer of 0 to 40.
- the total number of (meth)acryloyl groups is 5 or 6
- each n independently represents an integer of 0-10, and the sum of each n is an integer of 0-60.
- m is preferably an integer of 0-6, more preferably an integer of 0-4.
- the sum of m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
- n is preferably an integer of 0-6, more preferably an integer of 0-4.
- the sum of n is preferably an integer of 3-60, more preferably an integer of 3-24, and particularly preferably an integer of 6-12.
- diglycerin EO ethylene oxide modified (meth) acrylate
- pentaerythritol tetra (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-TMMT
- 1,6-hexanediol diacrylate manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 Toagosei Co., Ltd.
- 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 Chemicals Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
- photopolymerization initiators include trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbi 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 compounds, ⁇ -aminoketone compounds, and acylphosphine compounds, more preferably oxime compounds.
- hexaarylbiimidazole compounds include 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1′-biimidazole, etc. are mentioned.
- a benzoyl group may have a substituent.
- substituents include halogen atoms, cyano groups, nitro groups, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclicoxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, It is preferably an acyl group or an amino group, more preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group or an amino group.
- a sulfanyl group or an amino group is more preferred.
- R X12 is an electron-withdrawing group
- R X10 , R X11 , R X13 and R X14 are preferably hydrogen atoms.
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (for example, 50 mass ppm (parts per million), 10 mass ppm or less, or 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.
- the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a ppt (parts per trillion) level by mass may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (Chemical Daily, 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 size 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 content of peroxide in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
- the colored composition of the present invention does not substantially contain environmentally regulated substances.
- substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the colored composition is 50 ppm by mass or less, preferably 30 ppm by mass or less. , is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- Environmental control substances include, for example, benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.). Moreover, as a metal boride, the compound as described in international publication 2017/119394 can also be used.
- commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- the value of the number average molecular weight measured by the viscosity method is used.
- the value of the number average molecular weight in terms of polystyrene measured by the GPC (gel permeation chromatography) method is used.
- alkyleneimine examples include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine and the like, preferably ethyleneimine or propyleneimine, more preferably ethyleneimine. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. In addition, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more, of the primary amino group with respect to the total of the primary amino group, the secondary amino group and the tertiary amino group. , more preferably 30 mol % or more.
- Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, P-1000 (manufactured by Nippon Shokubai Co., Ltd.).
- the content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less.
- the content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more.
- the upper limit is preferably 10 parts by mass or less, more preferably 8 parts by mass or less. Only one kind of polyalkyleneimine may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention may contain a curing accelerator.
- Curing accelerators include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
- the curing accelerator include compounds described in paragraph numbers 0094 to 0097 of WO 2018/056189, compounds described in paragraph numbers 0246 to 0253 of JP 2015-034963, JP 2013-041165 Compounds described in paragraphs 0186 to 0251 of the publication, ionic compounds described in JP 2014-055114, compounds described in paragraphs 0071 to 0080 of JP 2012-150180, JP 2011-253054 Alkoxysilane compounds having an epoxy group described in JP-A-2005-200557, compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, and carboxy group-containing epoxy curing agents described in JP-A-2017-036379.
- the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
- Examples of functional groups other than hydrolyzable groups include vinyl group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group and isocyanate group. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferred.
- a block polymer can also be used as the fluorosurfactant.
- the fluorosurfactant has 2 or more (preferably 5 or more) repeating units derived from a (meth)acrylate compound having a fluorine atom and an alkyleneoxy group (preferably an ethyleneoxy group or a propyleneoxy group) (meta).
- 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 paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compound is preferably 3000-50000, for example 14000. In the above compounds, % indicating the ratio of repeating units is mol%.
- a fluoropolymer having an ethylenically unsaturated bond-containing group in a side chain can also be used as the fluorosurfactant.
- Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102 and RS-718K manufactured by DIC Corporation, and RS-72-K.
- compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
- antioxidants examples include 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 (manufactured by ADEKA Corporation) and the like.
- antioxidants are compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, compounds described in WO 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used.
- the water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the pore size of the filter is preferably 0.01-7.0 ⁇ m, more preferably 0.01-3.0 ⁇ m, and even more preferably 0.05-0.5 ⁇ 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 filter manufacturer's nominal value.
- Various filters provided by Nippon Pall Co., Ltd. (DFA4201NXEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nihon Entegris Co., Ltd. (former Japan Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd., etc. can be used as filters. .
- the wavelength at which the light transmittance is 50% is preferably in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and more preferably in the wavelength range of 480 to 520 nm. It is even more preferred to be present in the wavelength range. In particular, it is preferable that the wavelengths at which the light transmittance is 50% exist in both the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the wavelength on the short wavelength side at which the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm.
- Pattern formation by photolithography includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, a step of patternwise exposing the colored composition layer, and a step of exposing the colored composition layer. forming a pattern (pixels) by developing and removing the exposed portion. If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the underlayer may be formed using a composition obtained by removing the coloring agent from the colored composition described herein, or a composition containing the curable compound described herein, a surfactant, and the like.
- the surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferably 30 to 80° when measured with water.
- the colored composition layer formed on the support may be dried (pre-baked). Pre-baking may not be performed when the film is manufactured by a low-temperature process.
- the pre-baking 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, and can also be 80° C. or higher.
- the pre-bake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Pre-baking can be performed using a hot plate, an oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
- 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 selected as appropriate.
- the exposure may be in an oxygen-free atmosphere, or in a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume).
- the exposure illuminance can be set as appropriate, and is usually selected from a range of 1000 W/m 2 to 100000 W/m 2 (eg, 5000 W/m 2 , 15000 W/m 2 or 35000 W/m 2 ). can be done.
- the oxygen concentration and exposure illuminance may be appropriately combined.
- the illuminance may be 10000 W/m 2 at an oxygen concentration of 10% by volume and 20000 W/m 2 at an oxygen concentration of 35% by volume.
- 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. From the viewpoint of transportation and storage convenience, the developer may be produced once as a concentrated solution and then diluted to the required concentration when used. Although the dilution ratio is not particularly limited, it 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. Rinsing is preferably carried out by supplying a rinsing solution to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- optical filter of the present invention has the film of the present invention as described above.
- Types of optical filters include color filters and infrared transmission filters, with color filters being preferred.
- color filters it is preferable to have the film of the present invention as a colored pixel of the color filter.
- the solid-state imaging device of the present invention has the film of the present invention described above.
- the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device.
- G-1 compound having the following structure (ultraviolet absorber)
- G-2 compound having the following structure (compound having an epoxy group, weight average molecular weight: 3500)
- G-3 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2′-bis(hydroxymethyl)-1-butanol)
- G-4 A compound having the following structure (silane coupling agent)
- G-5 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent)
- G-6 p-methoxyphenol (polymerization inhibitor)
- G-7 Adekastab AO-80 (manufactured by ADEKA Corporation, antioxidant)
- the film prepared above was irradiated with light of 100,000 Lux for 2,000 hours using a light resistance tester (super xenon weather meter SX75, manufactured by Suga Test Instruments Co., Ltd.) (total irradiation amount: 200 million Lux hr. ).
- the transmittance of the film after light irradiation was measured, and the light resistance was evaluated according to the following criteria.
- B The viscosity increase rate of the coloring composition exceeds 5% and is 7.5% or less.
- C The viscosity increase rate of the coloring composition exceeds 7.5% and is 10% or less.
- D The viscosity increase rate of the coloring composition exceeds 10%.
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Abstract
Description
上記着色剤は、金属原子に、式(1)で表される化合物が配位している化合物Yを含む、着色組成物;
X2~X9はそれぞれ独立して窒素原子、CHまたはCRxを表し、
Rxは置換基を表し、
X2~X9のうち、隣接する2つがCRxである場合、隣接する2つのCRxのRx同士は結合して環を形成していてもよい;
ただし、式(1)は、以下の要件1~4いずれかの要件を満たしている;
要件1 X3~X5のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件2 X2とX3がCRxであり、かつ、X2が表すCRxのRxと、X3が表すCRxのRxとが結合してヘテロ環を形成している;
要件3 X6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件4 X2およびX3の少なくとも一方がCHであり、かつ、X2~X9のうち少なくとも1つがCRxである。
<2> 上記式(1)のX6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している、<1>に記載の着色組成物。
<3> 上記式(1)のX2~X9のうち少なくとも1つがCRxであり、Rxがヘテロ原子を含む基である、<1>または<2>に記載の着色組成物。
<4> 上記式(1)のX2~X9のうち少なくとも1つがCRxであり、Rxが、ニトロ基、シアノ基、-NR101R102、-OR103、-SR104、-COOR105、-OCOR106、-SO2R107、-SO2NR108R109、-SO2OR110、-CONR111R112または-NR113COR114を表し、R101およびR102はそれぞれ独立して、水素原子、アルキル基またはアリール基を表し、R101とR102は結合して環を形成していてもよく、R103~R114はそれぞれ独立して、アルキル基またはアリール基を表す、
<1>~<3>のいずれか1つに記載の着色組成物。
<5> 上記金属原子が、銅原子または亜鉛原子である、<1>~<4>のいずれか1つに記載の着色組成物。
<6> 上記金属原子が、銅原子である、<1>~<4>のいずれか1つに記載の着色組成物。
<7> 上記化合物Yの極大吸収波長が波長400~700nmの範囲に存在する、<1>~<6>のいずれか1つに記載の着色組成物。
<8> 上記着色剤は、更に、緑色着色剤を含む、<1>~<7>のいずれか1つに記載の着色組成物。
<9> 更に、重合性化合物と光重合開始剤を含む、<1>~<8>のいずれか1つに記載の着色組成物。
<10> カラーフィルタ用または赤外線透過フィルタ用である、<1>~<9>のいずれか1つに記載の着色組成物。
<11> <1>~<10>のいずれか1つに記載の着色組成物から得られる膜。
<12> <11>に記載の膜を有する光学フィルタ。
<13> <11>に記載の膜を有する固体撮像素子。
<14> <11>に記載の膜を有する画像表示装置。
<15> 金属原子に、式(1)で表される化合物が配位している化合物;
X2~X9はそれぞれ独立して窒素原子、CHまたはCRxを表し、
Rxは置換基を表し、
X2~X9のうち、隣接する2つがCRxである場合、隣接する2つのCRxのRx同士は結合して環を形成していてもよい;
ただし、式(1)は、以下の要件1~4いずれかの要件を満たしている;
要件1 X3~X5のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件2 X2とX3がCRxであり、かつ、X2が表すCRxのRxと、X3が表すCRxのRxとが結合してヘテロ環を形成している;
要件3 X6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件4 X2およびX3の少なくとも一方がCHであり、かつ、X2~X9のうち少なくとも1つがCRxである。 <1> A coloring composition containing a coloring agent and a resin,
A coloring composition in which the coloring agent contains a compound Y in which a compound represented by formula (1) is coordinated to a metal atom;
X 2 to X 9 each independently represents a nitrogen atom, CH or CR x ,
R x represents a substituent,
When adjacent two of X 2 to X 9 are CR x , R x of two adjacent CR x may combine to form a ring;
However, formula (1) satisfies any of the following requirements 1 to 4;
Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 2 X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring;
Requirement 3 Adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 to X 9 is CR x .
<2> Adjacent two of X 6 to X 9 in formula (1) are CR x , and R x of two adjacent CR x are bonded to form a ring, <1 > The coloring composition described in .
<3> The colored composition according to <1> or <2>, wherein at least one of X 2 to X 9 in formula (1) is CR x , and R x is a heteroatom-containing group.
<4> At least one of X 2 to X 9 in formula (1) is CR x , and R x is a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 , —COOR 105 , —OCOR 106 , —SO 2 R 107 , —SO 2 NR 108 R 109 , —SO 2 OR 110 , —CONR 111 R 112 or —NR 113 COR 114 , wherein R 101 and R 102 each independently represent , represents a hydrogen atom, an alkyl group or an aryl group, R 101 and R 102 may combine to form a ring, R 103 to R 114 each independently represent an alkyl group or an aryl group,
The colored composition according to any one of <1> to <3>.
<5> The colored composition according to any one of <1> to <4>, wherein the metal atom is a copper atom or a zinc atom.
<6> The colored composition according to any one of <1> to <4>, wherein the metal atom is a copper atom.
<7> The colored composition according to any one of <1> to <6>, wherein the compound Y has a maximum absorption wavelength in the wavelength range of 400 to 700 nm.
<8> The coloring composition according to any one of <1> to <7>, wherein the coloring agent further contains a green coloring agent.
<9> The colored composition according to any one of <1> to <8>, further comprising a polymerizable compound and a photopolymerization initiator.
<10> The colored composition according to any one of <1> to <9>, which is used for color filters or infrared transmission filters.
<11> A film obtained from the colored composition according to any one of <1> to <10>.
<12> An optical filter comprising the film according to <11>.
<13> A solid-state imaging device comprising the film according to <11>.
<14> An image display device comprising the film according to <11>.
<15> a compound in which a compound represented by formula (1) is coordinated to a metal atom;
X 2 to X 9 each independently represents a nitrogen atom, CH or CR x ,
R x represents a substituent,
When adjacent two of X 2 to X 9 are CR x , R x of two adjacent CR x may combine to form a ring;
However, formula (1) satisfies any of the following requirements 1 to 4;
Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 2 X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring;
Requirement 3 Adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 to X 9 is CR x .
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、構造式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において、顔料とは、溶剤に対して溶解しにくい色材を意味する。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。 The contents of the present invention will be described in detail below.
In the present specification, the term "~" is used to include the numerical values before and after it as lower and upper limits.
In the description of a group (atomic group) in the present specification, a description that does not describe substitution or unsubstituted includes a group (atomic group) having no substituent as well as a group (atomic group) having a substituent. For example, an "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In the present specification, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified. Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
In this specification, "(meth)acrylate" represents both or either acrylate and methacrylate, "(meth)acryl" represents both or either acrylic and methacrylic, and "(meth) ) acryloyl” refers to acryloyl and/or methacryloyl.
In the present specification, Me in the structural formulas represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group.
As used herein, the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
As used herein, the term "total solid content" refers to the total mass of all components of the composition excluding the solvent.
As used herein, the term "pigment" means a coloring material that is difficult to dissolve in a solvent.
As used herein, the term "process" includes not only an independent process, but also when the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. .
本発明の着色組成物は、着色剤と樹脂とを含む着色組成物であって、
上記着色剤は、金属原子に、式(1)で表される化合物が配位している化合物Yを含むことを特徴とする。 <Coloring composition>
The coloring composition of the present invention is a coloring composition containing a coloring agent and a resin,
The coloring agent is characterized by containing a compound Y in which a compound represented by formula (1) is coordinated to a metal atom.
本発明の着色組成物は着色剤を含有する。着色剤としては、金属原子に、式(1)で表される化合物が配位している化合物Yを含むものが用いられる。化合物Yは、アゾメチン金属錯体である。化合物Yは、本発明の化合物でもある。
X2~X9はそれぞれ独立して窒素原子、CHまたはCRxを表し、
Rxは置換基を表し、
X2~X9のうち、隣接する2つがCRxである場合、隣接する2つのCRxのRx同士は結合して環を形成していてもよい;
ただし、式(1)は、以下の要件1~4いずれかの要件を満たしている;
要件1 X3~X5のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件2 X2とX3がCRxであり、かつ、X2が表すCRxのRxと、X3が表すCRxのRxとが結合してヘテロ環を形成している;
要件3 X6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件4 X2およびX3の少なくとも一方がCHであり、かつ、X2~X9のうち少なくとも1つがCRxである。 <<coloring agent>>
The coloring composition of the present invention contains a coloring agent. As the colorant, one containing a compound Y in which a compound represented by formula (1) is coordinated to a metal atom is used. Compound Y is an azomethine metal complex. Compound Y is also a compound of the invention.
X 2 to X 9 each independently represents a nitrogen atom, CH or CR x ,
R x represents a substituent,
When two adjacent CR x among X 2 to X 9 are CR x, the R x of the two adjacent CR x may combine to form a ring;
However, formula (1) satisfies any of the following requirements 1 to 4;
Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 2 X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring;
Requirement 3 Adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 to X 9 is CR x .
式(1)のR1が表すアリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。アリール基は、置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。
式(1)のR1は水素原子またはアルキル基であることが好ましく、水素原子であることがより好ましい。 The number of carbon atoms in the alkyl group represented by R 1 in formula (1) is preferably 1-30, more preferably 1-15, and even more preferably 1-8. The alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear. The alkyl group may have a substituent. Substituents include the substituent T described later.
The aryl group represented by R 1 in formula (1) preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms. The aryl group may have a substituent. Substituents include the substituent T described later.
R 1 in formula (1) is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
R101~R114が表すアリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。アリール基は、置換基を有していてもよい。置換基としては、後述する置換基Tが挙げられる。 The number of carbon atoms in the alkyl group represented by R 101 to R 114 is preferably 1-10, more preferably 1-5, still more preferably 1-3, and particularly preferably 1 or 2. The alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear. The alkyl group may have a substituent. Substituents include the substituent T described below. The alkyl group represented by R 101 to R 114 is preferably a methyl group or an ethyl group.
The aryl group represented by R 101 to R 114 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms. The aryl group may have a substituent. Substituents include the substituent T described below.
R2~R9はそれぞれ独立して水素原子または置換基を表し、
R2~R9のうち、隣接する2つが結合して環を形成していてもよい;
ただし、式(1-1)は、以下の要件1a~4aいずれかの要件を満たしている;
要件1a R3~R5のうち隣接する2つが結合して環を形成している;
要件2a R2とR3とが結合してヘテロ環を形成している;
要件3a R6~R9のうち隣接する2つが結合して環を形成している;
要件4a R2およびR3の少なくとも一方が水素原子で、かつ、R2~R9のうち少なくとも1つが置換基である。 The compound represented by formula (1) is preferably a compound represented by formula (1-1).
R 2 to R 9 each independently represent a hydrogen atom or a substituent,
adjacent two of R 2 to R 9 may combine to form a ring;
However, formula (1-1) satisfies any of the following requirements 1a to 4a;
Requirement 1a adjacent two of R 3 to R 5 are bonded to form a ring;
Requirement 2a R 2 and R 3 are combined to form a heterocycle;
Requirement 3a adjacent two of R 6 to R 9 are bonded to form a ring;
Requirement 4a At least one of R 2 and R 3 is a hydrogen atom, and at least one of R 2 to R 9 is a substituent.
上述した置換基Tとして、次の基が挙げられる。ハロゲン原子(例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子)、アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、ヘテロ環基(好ましくは炭素数1~30のヘテロ環基)、アミノ基(好ましくは炭素数0~30のアミノ基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロ環オキシ基(好ましくは炭素数1~30のヘテロ環オキシ基)、アシル基(好ましくは炭素数2~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、ヘテロ環オキシカルボニル基(好ましくは炭素数2~30のヘテロ環オキシカルボニル基)、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アミノカルボニルアミノ基(好ましくは炭素数2~30のアミノカルボニルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、スルファモイルアミノ基(好ましくは炭素数0~30のスルファモイルアミノ基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロ環チオ基(好ましくは炭素数1~30のヘテロ環チオ基)、アルキルスルホニル基(好ましくは炭素数1~30のアルキルスルホニル基)、アルキルスルホニルアミノ基(好ましくは炭素数1~30のアルキルスルホニルアミノ基)、アリールスルホニル基(好ましくは炭素数6~30のアリールスルホニル基)、アリールスルホニルアミノ基(好ましくは炭素数6~30のアリールスルホニルアミノ基)、ヘテロ環スルホニル基(好ましくは炭素数1~30のヘテロ環スルホニル基)、ヘテロ環スルホニルアミノ基(好ましくは炭素数1~30のヘテロ環スルホニルアミノ基)、アルキルスルフィニル基(好ましくは炭素数1~30のアルキルスルフィニル基)、アリールスルフィニル基(好ましくは炭素数6~30のアリールスルフィニル基)、ヘテロ環スルフィニル基(好ましくは炭素数1~30のヘテロ環スルフィニル基)、ウレイド基(好ましくは炭素数1~30のウレイド基)、ヒドロキシ基、ニトロ基、カルボキシ基、スルホ基、リン酸基、カルボン酸アミド基、スルホン酸アミド基、イミド基、ホスフィノ基、メルカプト基、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、アリールアゾ基、ヘテロ環アゾ基、ホスフィニル基、ホスフィニルオキシ基、ホスフィニルアミノ基、シリル基、ヒドラジノ基、イミノ基。これらの基は、更に置換可能な基である場合、更に置換基を有してもよい。 (substituent T)
The following group is mentioned as the substituent T mentioned above. Halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (preferably alkyl group having 1 to 30 carbon atoms), alkenyl group (preferably 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 amino group having 0 to 30 carbon atoms), alkoxy group (preferably alkoxy group having 1 to 30 carbon atoms), aryloxy group (preferably aryloxy group having 6 to 30 carbon atoms), heterocyclic oxy group (preferably carbon 1 to 30 heterocyclic oxy groups), acyl groups (preferably acyl groups having 2 to 30 carbon atoms), alkoxycarbonyl groups (preferably alkoxycarbonyl groups having 2 to 30 carbon atoms), aryloxycarbonyl groups (preferably aryloxycarbonyl group having 7 to 30 carbon atoms), heterocyclicoxycarbonyl group (preferably heterocyclicoxycarbonyl group having 2 to 30 carbon atoms), acyloxy group (preferably acyloxy group having 2 to 30 carbon atoms), acylamino group (preferably acylamino group having 2 to 30 carbon atoms), aminocarbonylamino group (preferably aminocarbonylamino group having 2 to 30 carbon atoms), alkoxycarbonylamino group (preferably alkoxycarbonylamino group having 2 to 30 carbon atoms) , aryloxycarbonylamino group (preferably aryloxycarbonylamino group having 7 to 30 carbon atoms), sulfamoyl group (preferably sulfamoyl group having 0 to 30 carbon atoms), sulfamoylamino group (preferably 0 to 30 carbon atoms sulfamoylamino group), carbamoyl group (preferably carbamoyl group having 1 to 30 carbon atoms), alkylthio group (preferably alkylthio group having 1 to 30 carbon atoms), arylthio group (preferably arylthio group having 6 to 30 carbon atoms) group), heterocyclicthio group (preferably heterocyclicthio group having 1 to 30 carbon atoms), alkylsulfonyl group (preferably alkylsulfonyl group having 1 to 30 carbon atoms), alkylsulfonylamino group (preferably having 1 to 30 alkylsulfonylamino groups), arylsulfonyl groups (preferably arylsulfonyl groups having 6 to 30 carbon atoms), arylsulfonylamino groups (preferably arylsulfonylamino groups having 6 to 30 carbon atoms), heterocyclic sulfonyl groups (preferably is a C1-C30 heterocyclic sulfonyl group), heterocyclic sulfonylamino group (preferably heterocyclic sulfonylamino group having 1 to 30 carbon atoms), alkylsulfinyl group (preferably alkylsulfinyl group having 1 to 30 carbon atoms), arylsulfinyl group (preferably carbon number arylsulfinyl group of 6 to 30), heterocyclic sulfinyl group (preferably heterocyclic sulfinyl group of 1 to 30 carbon atoms), ureido group (preferably ureido group of 1 to 30 carbon atoms), hydroxy group, nitro group, carboxy group, sulfo group, phosphoric acid group, carboxylic acid amide group, sulfonic acid amide group, imide group, phosphino group, mercapto group, cyano group, alkylsulfino group, arylsulfino group, arylazo group, heterocyclic azo group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, hydrazino group, imino group. These groups may further have substituents if they are substitutable groups.
(1)赤色着色剤と青色着色剤と黄色着色剤とを含有する態様。
(2)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤とを含有する態様。
(3)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤と緑色着色剤とを含有する態様。
(4)赤色着色剤と青色着色剤と黄色着色剤と緑色着色剤とを含有する態様。
(5)黄色着色剤と紫色着色剤とを含有する態様。 In addition, the coloring agent contained in the coloring composition may include two or more chromatic coloring agents, and a combination of the two or more chromatic coloring agents may form a black color. Such a colored composition is preferably used as a colored composition for forming an infrared transmission filter. When two or more chromatic colorants are combined to form a black color, the combination of chromatic colorants includes the following.
(1) A mode containing a red colorant, a blue colorant and a yellow colorant.
(2) A mode containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
(3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant.
(4) A mode containing a red colorant, a blue colorant, a yellow colorant, and a green colorant.
(5) A mode containing a yellow colorant and a purple colorant.
本発明の着色組成物は樹脂を含む。樹脂は、例えば、顔料などを着色組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に顔料などを着色組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。 <<Resin>>
The coloring composition of the present invention contains a resin. The resin is blended, for example, for dispersing a pigment or the like in a coloring composition or as a binder. A resin mainly used for dispersing a pigment or the like in a coloring composition is also called a dispersant. However, such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
式(Y2):-C(=O)OC(RY4)(RY5)(RY6)
式(Y3):-C(RY7)(RY8)(ORY9)
式(Y4):-C(RY10)(H)(ArY1)
式(Y5):-C(=O)(RY11) Formula (Y1): -C(R Y1 )(R Y2 )(R Y3 )
Formula (Y2): -C(=O)OC(R Y4 )(R Y5 )(R Y6 )
Formula (Y3): -C(R Y7 )(R Y8 )(OR Y9 )
Formula (Y4): -C(R Y10 )(H)(Ar Y1 )
Formula (Y5): -C (=O) (R Y11 )
式(Y2)中、RY4~RY6は、各々独立にアルキル基を表し、RY4~RY6のうちの2つが結合して環を形成していてもよい;
式(Y3)中、RY7およびRY8は、各々独立に、水素原子、アルキル基またはアリール基を表し、RY7およびRY8の少なくとも一方がアルキル基またはアリール基であり、RY9は、アルキル基またはアリール基を表し、RY7またはRY8と、RY9とが結合して環を形成していてもよい;
式(Y4)中、ArY1は、アリール基を表し、RY10は、アルキル基またはアリール基を表す;
式(Y5)中、RY11は、アルキル基またはアリール基を表す。 In formula (Y1), R Y1 to R Y3 each independently represent an alkyl group, and two of R Y1 to R Y3 may combine to form a ring;
In formula (Y2), R Y4 to R Y6 each independently represent an alkyl group, and two of R Y4 to R Y6 may combine to form a ring;
In formula (Y3), R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl group. represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring;
In formula (Y4), Ar Y1 represents an aryl group, and R Y10 represents an alkyl group or an aryl group;
In formula (Y5), R Y11 represents an alkyl group or an aryl group.
アルキル基は、直鎖状、分岐状、環状のいずれでもよい。アルキル基の炭素数は1~12であることが好ましく、1~6であることがより好ましく、1~4であることがさらに好ましい。アリール基の炭素数は6~20が好ましく、6~12がより好ましい。RY7またはRY8と、RY9とが結合して形成される環としては、テトラヒドロフラニル基、テトラヒドロピラニル基等が挙げられる。式(Y3)において、RY7またはRY8と、RY9とが結合して環を形成していることが好ましい。また、RY7およびRY8の一方は水素原子であることが好ましい。 In formula (Y3), R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring.
Alkyl groups may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1-12, more preferably 1-6, even more preferably 1-4. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Examples of the ring formed by combining R Y7 or R Y8 with R Y9 include a tetrahydrofuranyl group and a tetrahydropyranyl group. In formula (Y3), R Y7 or R Y8 and R Y9 preferably combine to form a ring. Also, one of R Y7 and R Y8 is preferably a hydrogen atom.
式(B2)において、Xb2は3価の連結基を表し、Lb2は単結合または2価の連結基を表し、Zb2は酸基が保護基で保護された基を表す
式(B3)において、Xb3は3価の連結基を表し、Lb3は単結合または2価の連結基を表し、Zb3はエチレン性不飽和結合含有基を表す。 In Formula (B1), X b1 represents a trivalent linking group, L b1 represents a single bond or a divalent linking group, and Z b1 represents an acid group.
In formula (B2), X b2 represents a trivalent linking group, L b2 represents a single bond or a divalent linking group, and Z b2 represents a group in which an acid group is protected with a protecting group Formula (B3) In, X b3 represents a trivalent linking group, L b3 represents a single bond or a divalent linking group, and Z b3 represents an ethylenically unsaturated bond-containing group.
式(Ac-2)中、Ar10は芳香族カルボキシ基を含む基を表し、L11は、-COO-または-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。 Resin Ac is preferably a resin containing at least one repeating unit selected from repeating units represented by formula (Ac-1) and repeating units represented by formula (Ac-2).
In formula (Ac-2), Ar 10 represents a group containing an aromatic carboxyl group, L 11 represents -COO- or -CONH-, L 12 represents a trivalent linking group, P 10 represents a polymer represents a chain.
式(Ar-12)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1または2であることがより好ましく、2であることが更に好ましい。
式(Ar-13)中、n3およびn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1または2であることがより好ましく、1であることが更に好ましい。ただし、n3およびn4の少なくとも一方は1以上の整数である。
式(Ar-13)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基または上記式(Q-2)で表される基を表す。
式(Ar-11)~(Ar-13)中、*1はL1との結合位置を表す。 In formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, more preferably 2.
In formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and still more preferably 2.
In formula (Ar-13), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, preferably 1 More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
In formula (Ar-13), Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- 1) or a group represented by the above formula (Q-2).
In formulas (Ar-11) to (Ar-13), * 1 represents the bonding position with L1.
本発明の着色組成物は、重合性化合物を含有することが好ましい。重合性化合物としては、エチレン性不飽和結合含有基を有する化合物などが挙げられる。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本発明で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。 <<polymerizable compound>>
The coloring composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group. Examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups. The polymerizable compound used in the present invention is preferably a radically polymerizable compound.
式(Z-5)中、nは、0~6の整数が好ましく、0~4の整数がより好ましい。また、各nの合計は、3~60の整数が好ましく、3~24の整数がより好ましく、6~12の整数が特に好ましい。
また、式(Z-4)又は式(Z-5)中のE、すなわち-((CH2)yCH2O)-又は-((CH2)yCH(CH3)O)-は、酸素原子側の末端がXに結合する形態が好ましい。 In formula (Z-4), m is preferably an integer of 0-6, more preferably an integer of 0-4. The sum of m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
In formula (Z-5), n is preferably an integer of 0-6, more preferably an integer of 0-4. The sum of n is preferably an integer of 3-60, more preferably an integer of 3-24, and particularly preferably an integer of 6-12.
Further, E in formula (Z-4) or formula (Z-5), that is, -((CH 2 ) y CH 2 O)- or -((CH 2 ) y CH(CH 3 )O)- is A form in which the end on the oxygen atom side is bonded to X is preferred.
本発明の着色組成物は光重合開始剤を含有することができる。本発明の着色組成物が重合性化合物を含む場合、本発明の着色組成物は更に光重合開始剤を含有することが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。 <<Photoinitiator>>
The coloring composition of the present invention can contain a photopolymerization initiator. When the coloring composition of the present invention contains a polymerizable compound, the coloring composition of the present invention preferably further contains a photopolymerization initiator. 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 region to the visible region are preferred. The photopolymerization initiator is preferably a photoradical polymerization initiator.
RX2は、アルキル基、アルケニル基、アルコキシ基、アリール基、アリールオキシ基、ヘテロ環基、ヘテロ環オキシ基、アルキルスルファニル基、アリールスルファニル基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、アシルオキシ基またはアミノ基を表し、
RX3~RX14は、それぞれ独立して水素原子または置換基を表す;
ただし、RX10~RX14のうち少なくとも一つは、電子求引性基である。 The oxime compound OX is preferably at least one selected from the compounds represented by the formula (OX1) and the compounds represented by the formula (OX2), more preferably the compound represented by the formula (OX2). preferable.
R X2 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group, heterocyclicoxy group, alkylsulfanyl group, arylsulfanyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, aryl represents a sulfonyl group, an acyloxy group or an amino group,
R X3 to R X14 each independently represent a hydrogen atom or a substituent;
However, at least one of R X10 to R X14 is an electron-withdrawing group.
本発明の着色組成物は、溶剤を含有することが好ましい。溶剤としては、有機溶剤が挙げられる。溶剤の種類は、各成分の溶解性や組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、プロピレングリコールジアセテート、3-メトキシブタノール、メチルエチルケトン、ガンマブチロラクトン、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。 <<Solvent>>
The coloring composition of the present invention preferably contains a solvent. An organic solvent is mentioned as a solvent. The type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition. Organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For these details, reference can be made to paragraph 0223 of WO2015/166779, the content of which is incorporated herein. Ester-based solvents substituted with cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups can also be preferably used. Specific examples of 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, ethylcarbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxy butanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, isopropyl alcohol and the like. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (for example, 50 mass ppm (parts per million), 10 mass ppm or less, or 1 mass ppm or less).
本発明の着色組成物は、赤外線吸収剤をさらに含有することができる。例えば、本発明の着色組成物を用いて赤外線透過フィルタを形成する場合においては、着色組成物中に赤外線吸収剤を含有させることで得られる膜について透過させる光の波長をより長波長側にシフトさせることができる。赤外線吸収剤は、極大吸収波長を波長700nmよりも長波長側に有する化合物であることが好ましい。赤外線吸収剤は波長700nmを超え1800nm以下の範囲に極大吸収波長を有する化合物であることが好ましい。また、赤外線吸収剤の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。 <<Infrared Absorber>>
The coloring composition of the present invention can further contain an infrared absorbing agent. For example, in the case of forming an infrared transmission filter using the coloring composition of the present invention, the wavelength of the light transmitted through the film obtained by containing an infrared absorbing agent in the coloring composition is shifted to a longer wavelength side. can be made The infrared absorbing agent is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm. The infrared absorbing agent is preferably a compound having a maximum absorption wavelength in the range of 700 nm to 1800 nm. In addition, the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less. .
本発明の着色組成物は、顔料誘導体を含有することができる。顔料誘導体は例えば分散助剤として用いられる。顔料誘導体としては、色素骨格に酸基または塩基性基が結合した構造を有する化合物が挙げられる。 <<Pigment derivative>>
The coloring composition of the present invention can contain a pigment derivative. Pigment derivatives are used, for example, as dispersing aids. Pigment derivatives include compounds having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
また、顔料誘導体の含有量は、化合物Yの100質量部に対して5~50質量部が好ましく、10~40質量部がより好ましく、15~30質量部が更に好ましい。
顔料誘導体は1種のみを用いてもよいし、2種以上を併用してもよい。2種以上併用する場合はそれらの合計量が上記範囲であることが好ましい。 The content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 2 to 15 parts by mass, even more preferably 4 to 10 parts by mass, based on 100 parts by mass of the pigment.
The content of the pigment derivative is preferably 5 to 50 parts by mass, more preferably 10 to 40 parts by mass, and even more preferably 15 to 30 parts by mass with respect to 100 parts by mass of compound Y.
Only one pigment derivative may be used, or two or more pigment derivatives may be used in combination. When two or more are used in combination, the total amount thereof is preferably within the above range.
本発明の着色組成物は、ポリアルキレンイミンを含有することもできる。ポリアルキレンイミンは例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。ポリアルキレンイミンとは、アルキレンイミンを開環重合したポリマーのことである。ポリアルキレンイミンは、1級アミノ基と、2級アミノ基と、3級アミノ基とをそれぞれ含む分岐構造を有するポリマーであることが好ましい。アルキレンイミンの炭素数は2~6が好ましく、2~4がより好ましく、2または3であることが更に好ましく、2であることが特に好ましい。 <<Polyalkyleneimine>>
The coloring composition of the present invention can also contain a polyalkyleneimine. Polyalkyleneimines are used, for example, as dispersing aids for pigments. A dispersing aid is a material for enhancing dispersibility of a pigment in a coloring composition. Polyalkyleneimine is a polymer obtained by ring-opening polymerization of alkyleneimine. The polyalkyleneimine is preferably a polymer having a branched structure each containing a primary amino group, a secondary amino group and a tertiary amino group. The number of carbon atoms in the alkyleneimine is preferably 2 to 6, more preferably 2 to 4, still more preferably 2 or 3, and particularly preferably 2.
本発明の着色組成物は、硬化促進剤を含んでもよい。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2018/056189号の段落番号0094~0097に記載の化合物、特開2015-034963号公報の段落番号0246~0253に記載の化合物、特開2013-041165号公報の段落番号0186~0251に記載の化合物、特開2014-055114号公報に記載のイオン性化合物、特開2012-150180号公報の段落番号0071~0080に記載の化合物、特開2011-253054号公報に記載のエポキシ基を有するアルコキシシラン化合物、特許第5765059号公報の段落番号0085~0092に記載の化合物、特開2017-036379号公報に記載のカルボキシ基含有エポキシ硬化剤などが挙げられる。着色組成物の全固形分中における硬化促進剤の含有量は0.3~8.9質量%が好ましく、0.8~6.4質量%がより好ましい。 <<Curing accelerator>>
The coloring composition of the present invention may contain a curing accelerator. Curing accelerators include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like. Specific examples of the curing accelerator include compounds described in paragraph numbers 0094 to 0097 of WO 2018/056189, compounds described in paragraph numbers 0246 to 0253 of JP 2015-034963, JP 2013-041165 Compounds described in paragraphs 0186 to 0251 of the publication, ionic compounds described in JP 2014-055114, compounds described in paragraphs 0071 to 0080 of JP 2012-150180, JP 2011-253054 Alkoxysilane compounds having an epoxy group described in JP-A-2005-200557, compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, and carboxy group-containing epoxy curing agents described in JP-A-2017-036379. The content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などが挙げられる。このような化合物の具体例としては、特開2009-217221号公報の段落番号0038~0052、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。紫外線吸収剤の具体例としては、下記構造の化合物などが挙げられる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)、BASF社製のTinuvinシリーズ、Uvinul(ユビナール)シリーズ、住化ケムテックス(株)製のSumisorbシリーズなどが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物、国際公開第2016/181987号の段落番号0059~0076に記載された化合物、国際公開第2020/137819号に記載されたチオアリール基置換ベンゾトリアゾール型紫外線吸収剤を用いることもできる。
The coloring composition of the present invention can contain an ultraviolet absorber. Examples of ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, and triazine compounds. Specific examples of such compounds include paragraph numbers 0038 to 0052 of JP-A-2009-217221, paragraph numbers 0052-0072 of JP-A-2012-208374, and paragraph numbers 0317-0317 of JP-A-2013-068814. 0334, and compounds described in paragraphs 0061 to 0080 of JP-A-2016-162946, the contents of which are incorporated herein. Specific examples of the ultraviolet absorber include compounds having the following structures. Examples of commercially available UV absorbers include UV-503 (manufactured by Daito Chemical Co., Ltd.), Tinuvin series and Uvinul series manufactured by BASF, and Sumisorb series manufactured by Sumika Chemtex Co., Ltd. . Benzotriazole compounds include the MYUA series manufactured by Miyoshi Oil (Kagaku Kogyo Nippo, February 1, 2016). In addition, the ultraviolet absorber is a compound described in paragraph numbers 0049 to 0059 of Japanese Patent No. 6268967, a compound described in paragraph numbers 0059 to 0076 of WO 2016/181987, and WO 2020/137819. A thioaryl group-substituted benzotriazole-type ultraviolet absorber described in can also be used.
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。着色組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。重合禁止剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。 <<polymerization inhibitor>>
The coloring composition of the present invention can 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), 2,2′-methylenebis(4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. Only one kind of polymerization inhibitor may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount is preferably within the above range.
本発明の着色組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、N-β-アミノエチル-γ-アミノプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-602)、N-β-アミノエチル-γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-603)、N-β-アミノエチル-γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-602)、γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-903)、γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-903)、3-メタクリロキシプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-502)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-503)等がある。また、シランカップリング剤の具体例については、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。着色組成物の全固形分中におけるシランカップリング剤の含有量は、0.01~15.0質量%が好ましく、0.05~10.0質量%がより好ましい。シランカップリング剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。 <<Silane coupling agent>>
The coloring composition of the present invention can contain a silane coupling agent. In the present invention, a silane coupling agent means a silane compound having a hydrolyzable group and other functional groups. Further, the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and capable of forming a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Hydrolyzable groups include, for example, halogen atoms, alkoxy groups, acyloxy groups and the like, with alkoxy groups being 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 group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group and isocyanate group. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferred. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N-β-aminoethyl-γ-amino propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N-β-aminoethyl-γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxy Propylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-503), and the like. Further, specific examples of the silane coupling agent include compounds described in paragraph numbers 0018 to 0036 of JP-A-2009-288703 and compounds described in paragraph numbers 0056-0066 of JP-A-2009-242604. , the contents of which are incorporated herein. The content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. Only one kind of silane coupling agent may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount is preferably within the above range.
本発明の着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤はシリコーン系界面活性剤またはフッ素系界面活性剤であることが好ましい。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤を参照することができ、この内容は本明細書に組み込まれる。 <<Surfactant>>
The coloring composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants and silicone surfactants can be used. The surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant. For surfactants, reference can be made to surfactants described in paragraphs 0238-0245 of WO2015/166779, the contents of which are incorporated herein.
本発明の着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物、韓国公開特許第10-2019-0059371号公報に記載された化合物を使用することもできる。着色組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 <<Antioxidant>>
The coloring composition of the present invention can contain an antioxidant. Antioxidants include phenol compounds, phosphite ester compounds, thioether compounds and the like. Any phenolic compound known as a phenolic antioxidant can be used as the phenolic compound. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred. As the aforementioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred. The antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule. Phosphorus-based antioxidants can also be suitably used as antioxidants. As a phosphorus antioxidant, tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl ) oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like. Examples of commercially available antioxidants include 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 (manufactured by ADEKA Corporation) and the like. In addition, antioxidants are compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, compounds described in WO 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used. The content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one kind of antioxidant may be used, or two or more kinds thereof may be used. When two or more kinds are used, the total amount is preferably within the above range.
本発明の着色組成物は、必要に応じて、増感剤、硬化促進剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、本発明の着色組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。潜在酸化防止剤の市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。 <<Other Ingredients>>
The coloring composition of the present invention may optionally contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.). Properties such as film physical properties can be adjusted by appropriately containing these components. These components are, for example, described in JP 2012-003225, paragraph number 0183 and later (corresponding US Patent Application Publication No. 2013/0034812, paragraph number 0237), JP 2008-250074 paragraph The descriptions of numbers 0101 to 0104, 0107 to 0109, etc. can be referred to, and the contents thereof are incorporated herein. In addition, the coloring composition of the present invention may contain a latent antioxidant, if necessary. The latent antioxidant is a compound in which the site functioning as an antioxidant is protected by a protective group, and is heated at 100 to 250°C, or heated at 80 to 200°C in the presence of an acid/base catalyst. As a result, the protecting group is eliminated to function as an antioxidant. Examples of latent antioxidants include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219. Commercially available latent antioxidants include ADEKA Arkles GPA-5001 (manufactured by ADEKA Co., Ltd.).
着色組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料や着色組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、容器内壁は、容器内壁からの金属溶出を防ぎ、着色組成物の保存安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。 <<Container>>
The storage container for the coloring composition is not particularly limited, and known storage containers can be used. In addition, as a storage container, a multi-layer bottle whose inner wall is composed of 6 types and 6 layers of resins and a bottle with a 7-layer structure of 6 types of resins for the purpose of suppressing the contamination of raw materials and coloring compositions. It is also preferred to use Examples of such a container include the container described in JP-A-2015-123351. In addition, the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, enhancing the storage stability of the coloring composition, and suppressing deterioration of components.
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。 <Method for preparing coloring composition>
The coloring composition of the present invention can be prepared by mixing the aforementioned ingredients. In preparing the coloring composition, all components may be dissolved and / or dispersed in a solvent at the same time to prepare the coloring composition, and if necessary, each component may be appropriately mixed as two or more solutions or dispersions. , these may be mixed at the time of use (at the time of application) to prepare a colored composition.
本発明の膜は、上述した本発明の着色組成物から得られる膜である。本発明の膜は、カラーフィルタや赤外線透過フィルタなどの光学フィルタに用いることができる。 <Membrane>
The film of the present invention is a film obtained from the colored composition of the present invention described above. The film of the present invention can be used in optical filters such as color filters and infrared transmission filters.
(1):膜の厚み方向における光透過率の、波長400~640nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長800~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である。このような分光特性を有する膜は、波長400~640nmの範囲の光を遮光して、波長700nmを超える光を透過させることができる。
(2):膜の厚み方向における光透過率の、波長400~750nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長900~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~750nmの範囲の光を遮光して、波長850nmを超える光を透過させることができる。
(3):膜の厚み方向における光透過率の、波長400~830nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1000~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~830nmの範囲の光を遮光して、波長940nmを超える光を透過させることができる。
(4):膜の厚み方向における光透過率の、波長400~950nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1100~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~950nmの範囲の光を遮光して、波長1040nmを超える光を透過させることができる。 When the film of the present invention is used as an infrared transmission filter, the film of the present invention preferably has, for example, any one of the following spectral characteristics (1) to (4).
(1): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film. The minimum value of the ratio in the wavelength range of 800 to 1300 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 640 nm and transmit light in the wavelength range of 700 nm or more.
(2): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film. A film having a minimum modulus of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light in the wavelength range of 850 nm or more.
(3): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film. A film having a minimum modulus of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light in the wavelength range of 940 nm or more.
(4): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film. A film having a minimum modulus of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light in the wavelength range of 1040 nm or more.
次に、本発明の膜の製造方法について説明する。本発明の膜は、本発明の着色組成物を塗布する工程を経て製造できる。膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法、ドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。 <Method for manufacturing membrane>
Next, the method for producing the film of the present invention will be described. The film of the present invention can be produced through the step of applying the coloring composition of the present invention. Preferably, the film manufacturing method further includes a step of forming a pattern (pixels). A method for forming the pattern (pixels) includes a photolithography method and a dry etching method, and the photolithography method is preferable.
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、カラーフィルタおよび赤外線透過フィルタが挙げられ、カラーフィルタであることが好ましい。カラーフィルタとしては、カラーフィルタの着色画素として本発明の膜を有することが好ましい。 <Optical filter>
The optical filter of the present invention has the film of the present invention as described above. Types of optical filters include color filters and infrared transmission filters, with color filters being preferred. As a color filter, it is preferable to have the film of the present invention as a colored pixel of the color filter.
本発明の固体撮像素子は、上述した本発明の膜を有する。固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。 <Solid-state image sensor>
The solid-state imaging device of the present invention has the film of the present invention described above. The configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device.
本発明の画像表示装置は、上述した本発明の膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。 <Image display device>
The image display device of the present invention has the film of the present invention described above. Examples of image display devices include liquid crystal display devices and organic electroluminescence display devices. For a definition of an image display device and details of each image display device, see, for example, "Electronic Display Device (by Akio Sasaki, Industrial Research Institute, 1990)", "Display Device (by Junsho Ibuki, Sangyo Tosho ( Co., Ltd.), issued in 1989), etc. Liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Choukai Co., Ltd., 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied.
(合成例1) 化合物(Y-1)の合成
(Synthesis Example 1) Synthesis of compound (Y-1)
合成例1における化合物(a-1)および化合物(b-1)を、それぞれ下記表の化合物(a)の欄および化合物(b)の欄に記載の化合物に変更する以外は合成例1と同様の操作を行い、化合物(Y-2)~化合物(Y-44)、化合物(Y-48)、化合物(Y-50)、化合物(Y-52)、化合物(Y-56)、化合物(Y-87)を合成した。化合物(Y-2)~化合物(Y-44)、化合物(Y-48)、化合物(Y-50)、化合物(Y-52)、化合物(Y-56)、化合物(Y-87)は、銅原子に下記表の化合物Sの欄に記載の化合物が配位した化合物である。化合物(Y-2)~化合物(Y-44)、化合物(Y-48)、化合物(Y-50)、化合物(Y-52)、化合物(Y-56)、化合物(Y-87)の極大吸収波長は波長400~700nmの範囲に存在していた。なお、化合物Sとしてアミノ基を有する化合物を用いた場合には、錯体化の際に使用している酢酸と塩を形成していることもある。 (Synthesis Examples 2 to 44, 48, 50, 52, 56, 87) Compound (Y-2) to Compound (Y-44), Compound (Y-48), Compound (Y-50), Compound (Y-52) ), Compound (Y-56), Compound (Y-87) Synthesis of Compound (a-1) and Compound (b-1) in Synthesis Example 1, respectively, in the column of Compound (a) and Compound (b ) in the same manner as in Synthesis Example 1 except for changing to the compounds described in the column, compound (Y-2) to compound (Y-44), compound (Y-48), compound (Y-50), A compound (Y-52), a compound (Y-56), and a compound (Y-87) were synthesized. Compounds (Y-2) to Compound (Y-44), Compound (Y-48), Compound (Y-50), Compound (Y-52), Compound (Y-56) and Compound (Y-87) are It is a compound in which a compound described in the column of compound S in the table below is coordinated to a copper atom. Maximum of compound (Y-2) to compound (Y-44), compound (Y-48), compound (Y-50), compound (Y-52), compound (Y-56), compound (Y-87) Absorption wavelengths existed in the wavelength range of 400 to 700 nm. When a compound having an amino group is used as the compound S, it may form a salt with acetic acid used for complexation.
合成例1における化合物(a-1)および化合物(b-1)を、それぞれ下記表の化合物(a)の欄および化合物(b)の欄に記載の化合物に変更し、かつ、酢酸銅一水和物を酢酸亜鉛二水和物に変更した以外は合成例1と同様の操作を実施し、化合物(Y-45)、化合物(Y-46)、化合物(Y-47)、化合物(Y-49)、化合物(Y-51)、化合物(Y-53)、化合物(Y-54)、化合物(Y-55)、化合物(Y-57)、化合物(Y-68)~化合物(Y-86)を合成した。化合物(Y-45)、化合物(Y-46)、化合物(Y-47)、化合物(Y-49)、化合物(Y-51)、化合物(Y-53)、化合物(Y-54)、化合物(Y-55)、化合物(Y-57)、化合物(Y-68)~化合物(Y-86)は、亜鉛原子に下記表の化合物Sの欄に記載の化合物が配位した化合物である。化合物(Y-45)、化合物(Y-46)、化合物(Y-47)、化合物(Y-49)、化合物(Y-51)、化合物(Y-53)、化合物(Y-54)、化合物(Y-55)、化合物(Y-57)、化合物(Y-68)~化合物(Y-86)の極大吸収波長は波長400~600nmの範囲に存在していた。なお、化合物Sとしてアミノ基を有する化合物を用いた場合には、錯体化の際に使用している酢酸と塩を形成していることもある。 (Synthesis Examples 45, 46, 47, 49, 51, 53, 54, 55, 57, 68-86) Compound (Y-45), Compound (Y-46), Compound (Y-47), Compound (Y- 49), compound (Y-51), compound (Y-53), compound (Y-54), compound (Y-55), compound (Y-57), compound (Y-68) to compound (Y-86 ) Synthesis Compound (a-1) and Compound (b-1) in Synthesis Example 1 were changed to the compounds described in the columns of Compound (a) and Compound (b) in the table below, respectively, and acetic acid Compound (Y-45), compound (Y-46), compound (Y-47), compound (Y-47), compound (Y-49), compound (Y-51), compound (Y-53), compound (Y-54), compound (Y-55), compound (Y-57), compound (Y-68) to compound ( Y-86) was synthesized. Compound (Y-45), Compound (Y-46), Compound (Y-47), Compound (Y-49), Compound (Y-51), Compound (Y-53), Compound (Y-54), Compound (Y-55), compound (Y-57), compound (Y-68) to compound (Y-86) are compounds in which a compound described in the column of compound S in the table below is coordinated to a zinc atom. Compound (Y-45), Compound (Y-46), Compound (Y-47), Compound (Y-49), Compound (Y-51), Compound (Y-53), Compound (Y-54), Compound The maximum absorption wavelengths of (Y-55), compound (Y-57), compound (Y-68) to compound (Y-86) were in the wavelength range of 400 to 600 nm. When a compound having an amino group is used as the compound S, it may form a salt with acetic acid used for complexation.
合成例1における化合物(a-1)および化合物(b-1)を、それぞれ下記表の化合物(a)の欄および化合物(b)の欄に記載の化合物に変更し、かつ、酢酸銅一水和物を、酢酸鉄、チタンテトライソプロポキシド、塩基性酢酸アルミニウム、オルトケイ酸テトラエチルまたは酢酸カルシウム一水和物に変更した以外は合成例1と同様の操作を実施し、化合物(Y-58)~化合物(Y-67)を合成した。化合物(Y-58)~化合物(Y-67)は、下記表の金属原子の欄に記載の金属原子に下記表の化合物Sの欄に記載の化合物が配位した化合物である。化合物(Y-58)~化合物(Y-67)の極大吸収波長は波長400~600nmの範囲に存在していた。なお、化合物Sとしてアミノ基を有する化合物を用いた場合には、錯体化の際に使用している酢酸と塩を形成していることもある。 (Synthesis Examples 58 to 67) Synthesis of Compounds (Y-58) to (Y-67) column and compound (b) column, and copper acetate monohydrate is replaced with iron acetate, titanium tetraisopropoxide, basic aluminum acetate, tetraethyl orthosilicate or calcium acetate monohydrate Compounds (Y-58) to (Y-67) were synthesized in the same manner as in Synthesis Example 1, except that Compounds (Y-58) to (Y-67) are compounds in which the metal atom described in the metal atom column of the table below is coordinated with the compound described in the compound S column of the table below. The maximum absorption wavelengths of compounds (Y-58) to (Y-67) existed in the wavelength range of 400 to 600 nm. When a compound having an amino group is used as the compound S, it may form a salt with acetic acid used for complexation.
下記表に記載の原料を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm2および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。なお、以下の表において、着色剤1~4、赤外線吸収剤、顔料誘導体および分散剤の配合量の値は固形分換算での値である。 <Production of dispersion liquid>
A mixed liquid obtained by mixing raw materials shown in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads with a diameter of 0.1 mm). Then, dispersion treatment was carried out using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a decompression mechanism under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersing treatment was repeated 10 times to obtain a dispersion. In the table below, the amounts of colorants 1 to 4, infrared absorbers, pigment derivatives and dispersants are values in terms of solid content.
Y-1~Y-87:上述した化合物Y-1~Y-87
Yb-1:下記構造の化合物(C.I.ピグメントイエロー129)
PG58 : C.I.ピグメントグリーン58(フタロシアニン化合物、緑色顔料)
PG59 : C.I.ピグメントグリーン59(フタロシアニン化合物、緑色顔料)
PG63 : C.I.ピグメントグリーン63(フタロシアニン化合物、緑色顔料)
PR254 : C.I.ピグメントレッド254(ジケトピロロピロール化合物、赤色顔料)
PR264 : C.I.ピグメントレッド264(ジケトピロロピロール化合物、赤色顔料)
PR272 : C.I.ピグメントレッド272(ジケトピロロピロール化合物、赤色顔料)
PY139 : C.I.ピグメントイエロー139(イソインドリン化合物、黄色顔料)
PY150 : C.I.ピグメントイエロー150(アゾ化合物、黄色顔料)
PY155 : C.I.ピグメントイエロー155(アゾ化合物、黄色顔料)
PY185 : C.I.ピグメントイエロー185(イソインドリン化合物、黄色顔料)
PY215 : C.I.ピグメントイエロー215(プテリジン化合物、黄色顔料)
PO71 : C.I.ピグメントオレンジ71(ジケトピロロピロール化合物、オレンジ色顔料)
PB15:6 : C.I.ピグメントブルー15:6(フタロシアニン化合物、青色顔料) (coloring agent)
Y-1 to Y-87: compounds Y-1 to Y-87 described above
Yb-1: a compound having the following structure (C.I. Pigment Yellow 129)
PG58: C.I. I. Pigment Green 58 (phthalocyanine compound, green pigment)
PG59: C.I. I. Pigment Green 59 (phthalocyanine compound, green pigment)
PG63: C.I. I. Pigment Green 63 (phthalocyanine compound, green pigment)
PR254: C.I. I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment)
PR264: C.I. I. Pigment Red 264 (diketopyrrolopyrrole compound, red pigment)
PR272: C.I. I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
PY139: C.I. I. Pigment Yellow 139 (isoindoline compound, yellow pigment)
PY150: C.I. I. Pigment Yellow 150 (azo compound, yellow pigment)
PY155: C.I. I. Pigment Yellow 155 (azo compound, yellow pigment)
PY185: C.I. I. Pigment Yellow 185 (isoindoline compound, yellow pigment)
PY215: C.I. I. Pigment Yellow 215 (pteridine compound, yellow pigment)
PO71: C.I. I. Pigment Orange 71 (diketopyrrolopyrrole compound, orange pigment)
PB15:6: C.I. I. Pigment Blue 15:6 (phthalocyanine compound, blue pigment)
B-1:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量24000)
還流冷却器、滴下ロート及び撹拌機を備えたフラスコ内に窒素を適量流し、窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート(PGMEA)の340質量部を入れ、撹拌しながら80℃まで加熱した。次いで、アクリル酸の57質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレート及び3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)の54質量部、ベンジルメタクリレートの239質量部、PGMEAの73質量部の混合溶液を5時間かけて滴下した。次いで、重合開始剤(2,2-アゾビス(2,4-ジメチルバレロニトリル))の40質量部をPGMEAの197質量部に溶解した溶液を6時間かけて滴下した。重合開始剤溶液の滴下終了後、80℃で3時間保持した後、室温まで冷却して下記構造の樹脂を得た。得られた樹脂の重量平均分子量は9400、分散度は1.89、酸価は114mgKOH/gであった。
B-1: Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 24,000)
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA) (solvent)
Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
下記の表に記載の原料を混合して、着色組成物を製造した。 <Production of coloring composition>
A coloring composition was produced by mixing the raw materials shown in the table below.
分散液1~79、101~133、201~251、比較分散液1、2:上述した分散液1~79、比較分散液1、2 (dispersion liquid)
Dispersions 1 to 79, 101 to 133, 201 to 251, Comparative Dispersions 1, 2: Dispersions 1 to 79 described above, Comparative Dispersions 1, 2
B-1:上述した分散剤B-1
B-4:上述した分散剤B-4
C-1:下記構造の樹脂(主鎖に付記した数値はモル比である。重量平均分子量11000)
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、1-メトキシ-2-プロピルアセテ-ト371質量部を入れ、攪拌しながら85℃まで加熱した。次いで、アクリル酸54質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8と9-イルアクリレートの混合物225質量部、ビニルトルエン(異性体混合物)81質量部、1-メトキシ-2-プロピルアセテ-ト80質量部の混合溶液を4時間かけて滴下した。一方、重合開始剤2,2-アゾビス(2,4-ジメチルバレロニトリル)30質量部を1-メトキシ-2-プロピルアセテ-ト160質量部に溶解した溶液を5時間かけて滴下した。開始剤溶液の滴下終了後、4時間85℃で保持した後、室温まで冷却して樹脂を得た。得られた樹脂の重量平均分子量は10600、分散度は2.01、酸価は43mgKOH/gであった。 (binder)
B-1: Dispersant B-1 described above
B-4: Dispersant B-4 described above
C-1: Resin having the following structure (numerical values attached to the main chain are molar ratios. Weight average molecular weight: 11000)
D-1:下記構造の化合物
D-5:EBECRYL80(ダイセル・オルネクス社製、アミン含有4官能アクリレート)
D-6:エトキシ化ジペンタエリスリトールヘキサメタクリレート (monomer)
D-1: A compound having the following structure
D-5: EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
D-6: ethoxylated dipentaerythritol hexamethacrylate
E-1~E-4:下記構造の化合物
E-5:2,2’,4-トリス(2-クロロフェニル)-5-(3,4-ジメトキシフェニル)-4,5-ジフェニル-1,1’-ビイミダゾール
E-1 to E-4: compounds having the following structures E-5: 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1 '-Biimidazole
F-1:KF-6001(信越化学工業(株)製、シリコーン系界面活性剤、両末端カルビノール変性ポリジメチルシロキサン、ヒドロキシ基価62mgKOH/g)
F-2:下記構造の化合物(重量平均分子量14000)。下記の式中、繰り返し単位の割合を示す%はモル%である。(フッ素系界面活性剤)
F-4:BYK-330(ビックケミー社製、シリコーン系界面活性剤)
F-5:DOWSIL SH8400 FLUID(ダウ・東レ(株)製、シリコーン系界面活性剤) (Surfactant)
F-1: KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant, carbinol-modified polydimethylsiloxane at both ends, hydroxy value 62 mgKOH/g)
F-2: A compound having the following structure (weight average molecular weight: 14,000). In the following formulas, % indicating the ratio of repeating units is mol %. (Fluorine surfactant)
F-4: BYK-330 (manufactured by BYK-Chemie, silicone surfactant)
F-5: DOWSIL SH8400 FLUID (manufactured by Dow Toray Industries, Inc., silicone surfactant)
G-1:下記構造の化合物(紫外線吸収剤)
G-4:下記構造の化合物(シランカップリング剤)
G-6:p-メトキシフェノール(重合禁止剤)
G-7:アデカスタブ AO-80((株)ADEKA製、酸化防止剤) (Additive)
G-1: compound having the following structure (ultraviolet absorber)
G-4: A compound having the following structure (silane coupling agent)
G-6: p-methoxyphenol (polymerization inhibitor)
G-7: Adekastab AO-80 (manufactured by ADEKA Corporation, antioxidant)
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
Z-2:プロピレングリコールモノメチルエーテル(PGME)
Z-3:シクロペンタノン
Z-4:シクロヘキサノン
Z-5:アニソール
Z-6:ジアセトンアルコール (solvent)
Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
Z-2: propylene glycol monomethyl ether (PGME)
Z-3: cyclopentanone Z-4: cyclohexanone Z-5: anisole Z-6: diacetone alcohol
上記表に記載の実施例および比較例の着色組成物をガラス基板上にスピンコート法で塗布し、次いで、ホットプレートを使用して100℃120秒加熱処理(プリベーク)し、次いでi線で1000mJ/cm2の露光量で露光し、次いで、200℃で5分間加熱を行い、厚さ0.6μmの膜を作製した。得られた膜について、大塚電子(株)製のMCPD-3000を用い、波長400~700nmの範囲の光透過率(透過率)を測定した。次に、上記で作製した膜に対し、耐光試験機(スーパーキセノンウェザーメーターSX75、スガ試験機株式会社製)を用いて100000Luxの光を2000時間かけて照射した(総照射量2億Lux・hr)。光照射後の膜の透過率を測定し、以下の基準にて耐光性を評価した。
A:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の98%以上である。
B:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の95%以上98%未満である。
C:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の93%以上95%未満である。
D:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の90%以上93%未満である。
E:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の90%未満である。 [Light resistance evaluation]
The coloring compositions of the examples and comparative examples shown in the table above were applied to a glass substrate by spin coating, then heat-treated (pre-baked) at 100° C. for 120 seconds using a hot plate, and then i-line at 1000 mJ. /cm 2 and then heated at 200°C for 5 minutes to form a film with a thickness of 0.6 µm. The obtained film was measured for light transmittance (transmittance) in a wavelength range of 400 to 700 nm using MCPD-3000 manufactured by Otsuka Electronics Co., Ltd. Next, the film prepared above was irradiated with light of 100,000 Lux for 2,000 hours using a light resistance tester (super xenon weather meter SX75, manufactured by Suga Test Instruments Co., Ltd.) (total irradiation amount: 200 million Lux hr. ). The transmittance of the film after light irradiation was measured, and the light resistance was evaluated according to the following criteria.
A: The integrated value of the transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is 98% or more of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 to 700 nm.
B: The integrated transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is 95% or more and less than 98% of the integrated transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
C: The integrated transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is 93% or more and less than 95% of the integrated transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
D: The integrated value of the transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is 90% or more and less than 93% of the integrated value of the transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
E: The integrated value of the transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is less than 90% of the integrated value of the transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
製造直後の上記表に記載の実施例および比較例の着色組成物の粘度を測定した。粘度を測定した着色組成物を45℃の恒温槽で72時間保管したのち、粘度を測定した。なお、粘度は、着色組成物の温度を23℃に調整して測定した。以下の計算式から増粘率を算出し、保存安定性を評価した。
増粘率(%)=((45℃の恒温槽で72時間保管後の着色組成物の粘度/製造直後の着色組成物の粘度)-1)×100
A:着色組成物の増粘率が5%以下である。
B:着色組成物の増粘率が5%を超えて、7.5%以下である。
C:着色組成物の増粘率が7.5%を超えて、10%以下である。
D:着色組成物の増粘率が10%を超えている。 [Storage stability]
The viscosities of the colored compositions of Examples and Comparative Examples listed in the above table were measured immediately after production. The viscosity was measured after storing the coloring composition which measured the viscosity for 72 hours in a 45 degreeC constant temperature bath. The viscosity was measured by adjusting the temperature of the coloring composition to 23°C. The viscosity increase rate was calculated from the following formula, and the storage stability was evaluated.
Thickening rate (%) = ((viscosity of the coloring composition after storage for 72 hours in a constant temperature bath at 45 ° C. / viscosity of the coloring composition immediately after production) -1) × 100
A: The viscosity increase rate of the coloring composition is 5% or less.
B: The viscosity increase rate of the coloring composition exceeds 5% and is 7.5% or less.
C: The viscosity increase rate of the coloring composition exceeds 7.5% and is 10% or less.
D: The viscosity increase rate of the coloring composition exceeds 10%.
Claims (15)
- 着色剤と樹脂とを含む着色組成物であって、
前記着色剤は、金属原子に、式(1)で表される化合物が配位している化合物Yを含む、着色組成物;
X2~X9はそれぞれ独立して窒素原子、CHまたはCRxを表し、
Rxは置換基を表し、
X2~X9のうち、隣接する2つがCRxである場合、隣接する2つのCRxのRx同士は結合して環を形成していてもよい;
ただし、式(1)は、以下の要件1~4いずれかの要件を満たしている;
要件1 X3~X5のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件2 X2とX3がCRxであり、かつ、X2が表すCRxのRxと、X3が表すCRxのRxとが結合してヘテロ環を形成している;
要件3 X6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件4 X2およびX3の少なくとも一方がCHであり、かつ、X2~X9のうち少なくとも1つがCRxである。 A coloring composition containing a coloring agent and a resin,
A coloring composition in which the coloring agent comprises a compound Y in which a compound represented by formula (1) is coordinated to a metal atom;
X 2 to X 9 each independently represents a nitrogen atom, CH or CR x ,
R x represents a substituent,
When adjacent two of X 2 to X 9 are CR x , R x of two adjacent CR x may combine to form a ring;
However, formula (1) satisfies any of the following requirements 1 to 4;
Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 2 X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring;
Requirement 3 Adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 to X 9 is CR x . - 前記式(1)のX6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している、請求項1に記載の着色組成物。 2. The formula (1) according to claim 1, wherein adjacent two of X 6 to X 9 in formula (1) are CR x , and R x of two adjacent CR x are bonded to form a ring. coloring composition.
- 前記式(1)のX2~X9のうち少なくとも1つがCRxであり、Rxがヘテロ原子を含む基である、請求項1または2に記載の着色組成物。 3. The coloring composition according to claim 1, wherein at least one of X 2 to X 9 in formula (1) is CR x , and R x is a heteroatom-containing group.
- 前記式(1)のX2~X9のうち少なくとも1つがCRxであり、Rxが、ニトロ基、シアノ基、-NR101R102、-OR103、-SR104、-COOR105、-OCOR106、-SO2R107、-SO2NR108R109、-SO2OR110、-CONR111R112または-NR113COR114を表し、R101およびR102はそれぞれ独立して、水素原子、アルキル基またはアリール基を表し、R101とR102は結合して環を形成していてもよく、R103~R114はそれぞれ独立して、アルキル基またはアリール基を表す、
請求項1~3のいずれか1項に記載の着色組成物。 At least one of X 2 to X 9 in formula (1) is CR x , and R x is a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 , —COOR 105 , — OCOR 106 , —SO 2 R 107 , —SO 2 NR 108 R 109 , —SO 2 OR 110 , —CONR 111 R 112 or —NR 113 COR 114 , wherein R 101 and R 102 each independently represent a hydrogen atom , represents an alkyl group or an aryl group, R 101 and R 102 may combine to form a ring, R 103 to R 114 each independently represent an alkyl group or an aryl group,
The coloring composition according to any one of claims 1-3. - 前記金属原子が、銅原子または亜鉛原子である、請求項1~4のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 4, wherein the metal atom is a copper atom or a zinc atom.
- 前記金属原子が、銅原子である、請求項1~4のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 4, wherein the metal atom is a copper atom.
- 前記化合物Yの極大吸収波長が波長400~700nmの範囲に存在する、請求項1~6のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 6, wherein the compound Y has a maximum absorption wavelength in the wavelength range of 400 to 700 nm.
- 前記着色剤は、更に、緑色着色剤を含む、請求項1~7のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 7, wherein the coloring agent further comprises a green coloring agent.
- 更に、重合性化合物と光重合開始剤を含む、請求項1~8のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 8, further comprising a polymerizable compound and a photopolymerization initiator.
- カラーフィルタ用または赤外線透過フィルタ用である、請求項1~9のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 9, which is for a color filter or an infrared transmission filter.
- 請求項1~10のいずれか1項に記載の着色組成物から得られる膜。 A film obtained from the colored composition according to any one of claims 1 to 10.
- 請求項11に記載の膜を有する光学フィルタ。 An optical filter having the film according to claim 11.
- 請求項11に記載の膜を有する固体撮像素子。 A solid-state imaging device having the film according to claim 11.
- 請求項11に記載の膜を有する画像表示装置。 An image display device comprising the film according to claim 11.
- 金属原子に、式(1)で表される化合物が配位している化合物;
X2~X9はそれぞれ独立して窒素原子、CHまたはCRxを表し、
Rxは置換基を表し、
X2~X9のうち、隣接する2つがCRxである場合、隣接する2つのCRxのRx同士は結合して環を形成していてもよい;
ただし、式(1)は、以下の要件1~4いずれかの要件を満たしている;
要件1 X3~X5のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件2 X2とX3がCRxであり、かつ、X2が表すCRxのRxと、X3が表すCRxのRxとが結合してヘテロ環を形成している;
要件3 X6~X9のうち隣接する2つがCRxであり、かつ、隣接する2つのCRxのRx同士が結合して環を形成している;
要件4 X2およびX3の少なくとも一方がCHであり、かつ、X2~X9のうち少なくとも1つがCRxである。 A compound in which a compound represented by formula (1) is coordinated to a metal atom;
X 2 to X 9 each independently represents a nitrogen atom, CH or CR x ,
R x represents a substituent,
When adjacent two of X 2 to X 9 are CR x , R x of two adjacent CR x may combine to form a ring;
However, formula (1) satisfies any of the following requirements 1 to 4;
Requirement 1 Adjacent two of X 3 to X 5 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 2 X 2 and X 3 are CR x , and R x of CR x represented by X 2 and R x of CR x represented by X 3 combine to form a heterocyclic ring;
Requirement 3 Adjacent two of X 6 to X 9 are CR x , and the R x 's of the two adjacent CR x 's are bonded to form a ring;
Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 to X 9 is CR x .
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JP2022579503A JPWO2022168741A1 (en) | 2021-02-03 | 2022-01-28 | |
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