WO2022168742A1 - 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 - Google Patents
着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 Download PDFInfo
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- WO2022168742A1 WO2022168742A1 PCT/JP2022/003237 JP2022003237W WO2022168742A1 WO 2022168742 A1 WO2022168742 A1 WO 2022168742A1 JP 2022003237 W JP2022003237 W JP 2022003237W WO 2022168742 A1 WO2022168742 A1 WO 2022168742A1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 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
- 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
- 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
- 239000008188 pellet Substances 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
- 125000004193 piperazinyl 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
- 239000000843 powder Substances 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
- 239000012264 purified product Substances 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
- 230000009467 reduction Effects 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
- 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 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
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 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 studies of the present inventors, 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.
- an object of the present invention is to provide a coloring composition capable of forming a film with excellent light resistance.
- Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, an image display device, and a compound.
- the present invention provides the following.
- a coloring composition containing a coloring agent and a resin contains a compound Y in which a compound represented by formula (1) is coordinated to a metal atom, A coloring composition in which the content of the compound Y in the total solid content of the coloring composition is 10% by mass or more;
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 11 each independently represent a hydrogen atom or a substituent; adjacent two of R 2 to R 11 may combine to form a ring; However, at least one of R 2 to R 11 is a substituent.
- At least one of R 2 to R 11 in formula (1) is a nitro group, a cyano group, —NR 101 R 102 , —OR 103 , —SR 104 , —COOR 105 , —OCOR 106 , —SO 2R 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, an alkyl group or an aryl 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 ⁇ 1>.
- ⁇ 4> The colored composition according to any one of ⁇ 1> to ⁇ 3>, wherein the metal atom is a copper atom or a zinc atom.
- ⁇ 5> The colored composition according to any one of ⁇ 1> to ⁇ 3>, wherein the metal atom is a copper atom.
- ⁇ 6> The colored composition according to any one of ⁇ 1> to ⁇ 5>, wherein the compound Y has a maximum absorption wavelength in the wavelength range of 400 to 700 nm.
- ⁇ 7> The coloring composition according to any one of ⁇ 1> to ⁇ 6>, wherein the coloring agent further contains a green coloring agent.
- ⁇ 8> The colored composition according to any one of ⁇ 1> to ⁇ 7>, further comprising a polymerizable compound and a photopolymerization initiator.
- ⁇ 9> The colored composition according to any one of ⁇ 1> to ⁇ 8>, which is used for color filters or infrared transmission filters.
- ⁇ 10> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 9>.
- ⁇ 11> An optical filter comprising the film according to ⁇ 10>.
- ⁇ 12> A solid-state imaging device having the film according to ⁇ 10>.
- ⁇ 13> An image display device comprising the film according to ⁇ 10>.
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 11 each independently represent a hydrogen atom or a substituent; adjacent two of R 2 to R 11 may combine to form a ring; provided that at least one of R 2 to R 11 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 ; R 101 and R 102 each independently represent a hydrogen atom, an alkyl group or an aryl group ; 102 may combine to form a ring, and R 103 to R 114 each independently represent an alkyl
- the present invention it is possible to provide a colored composition capable of forming a film with excellent light resistance. Also, films, optical filters, solid-state imaging devices, image display devices and compounds can be provided.
- ⁇ is used to include the numerical values before and after it as lower and upper limits.
- 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.
- 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).
- 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.
- Me in the structural formulas represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
- total solid content refers to the total mass of all components of the composition excluding the solvent.
- a pigment means a compound that is difficult to dissolve in a solvent.
- 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. .
- the coloring composition of the present invention is a coloring composition containing a coloring agent and a resin, wherein the coloring agent contains a compound Y in which a compound represented by formula (1) is coordinated to a metal atom. , wherein the content of the compound Y in the total solid content of the coloring composition is 10% by mass or more.
- the coloring composition of the present invention a film with excellent light resistance can be formed.
- Compound Y which is used as a colorant in the coloring composition of the present invention, is presumed to readily form associations in the film and to efficiently transfer electrons between molecules.
- the coloring composition of the present invention contains 10% by mass or more of this compound Y in the total solid content of the coloring composition, when forming a film using the coloring composition, in the film It is speculated that the association of compound Y is promoted more. For these reasons, it is presumed that the use of the coloring composition of the present invention enabled the formation of a film with excellent light resistance.
- the colored composition of the present invention also has excellent storage stability, and can suppress changes in viscosity over time.
- 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 wavelength on the long wavelength side at which the light transmittance is 50% preferably exists in the wavelength range of 580 to 620 nm, more preferably in the wavelength range of 585 to 615 nm.
- a coloring composition capable of forming a film having such spectral characteristics is preferably used as a coloring composition for forming green pixels of a color filter.
- the coloring composition of the present invention contains a coloring agent.
- a coloring agent 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.
- the content of compound Y in the total solid content of the coloring composition is 10% by mass or more, preferably 10 to 40% by mass, more preferably 10 to 35% by mass, 10 to 30% by mass % or less.
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 11 each independently represent a hydrogen atom or a substituent; adjacent two of R 2 to R 11 may combine to form a ring; However, at least one of R 2 to R 11 is a substituent.
- 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 below.
- 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 even more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent.
- Substituents include the substituent T described below.
- R 1 in formula (1) is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
- Substituents represented by R 2 to R 11 in formula (1) include a substituent T described later, preferably a group containing a hetero atom, and more preferably a specific functional group A described later.
- 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 , nitro group, cyano group, —NR 101 R 102 , —OR 103 , —SR 104 , —COOR 105 , —CONR 111 R 112 and -CONR 111 R 112 is 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 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 groups represented by R 101 to R 114 are preferably methyl groups or ethyl groups.
- 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.
- R 101 and R 102 may combine to form a ring.
- Examples of the ring formed by combining R 101 and R 102 include pyrrolidine ring, piperidine ring, piperazine ring and morpholine ring.
- R 101 and R 102 are each independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom, a methyl group or an ethyl group.
- R 103 to R 114 are each independently preferably an alkyl group, more preferably a methyl group or an ethyl group.
- Adjacent two of R 2 to R 11 in formula (1) may combine to form a ring.
- the ring 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.
- the ring formed include a benzene ring, a hydrocarbon ring such as a naphthalene ring, a dioxane ring, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, imidazoline ring, pyridazine ring, pyrimidine ring, pyrazine ring, indole ring, isoindole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, benzotriazole ring, purine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, Heterocycles such as cinnoline ring, pteridine ring, pyrrolidine ring
- At least one of R 2 to R 11 in formula (1) is a substituent, and is preferably a group containing a heteroatom because a film having more excellent light resistance can be formed.
- the specific functional group A is more preferred.
- 1 to 4 (more preferably 1 or 2, still more preferably 1) of R 2 to R 11 in formula (1) are preferably substituents, and are groups containing heteroatoms. is preferred, and the specific functional group A described above is more preferred.
- at least one of R 3 , R 4 , R 5 , R 6 , R 9 and R 10 (preferably R At least one of 9 and R 10 , more preferably R 9 ) is preferably a substituent, preferably a heteroatom-containing group, more preferably the specific functional group A described above.
- At least one of R 3 , R 4 , R 5 , R 6 , R 9 and R 10 is a heteroatom-containing group (preferably the above-mentioned specific functional group A), and the rest are hydrogen atoms.
- 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 to the metal atom. Further, the metal atom may be coordinated with a ligand other than the compound represented by formula (1).
- Ligands include heterocyclic compounds (e.g., pyridine, pyrimidine, imidazole, pyrazole, triazole, tetrazole, quinoline, 1,10-phenanthroline, etc.), protic compounds (e.g., water, methanol, ethanol, etc.), amine compounds ( For example, triethylamine, N,N,N',N'-tetramethylenediamine, ethylenediaminetetraacetic acid N,N,N',N'',N''-pentamethyldiethylenetriamine, etc.), amide compounds (for example, N,N- dimethylacetamide, N-methylpyrrolidone, etc.), dimethylsulfoxide, sulfolane, nitrile compounds (eg, acetonitrile, etc.), and the like.
- heterocyclic compounds e.g., pyridine, pyrimidine, imidazole, pyrazole, triazole, t
- Compound Y may also be a binuclear complex.
- examples of the compound Y include the compound represented by the following formula (1-1) and the compound represented by the formula (1-2). compounds, compounds represented by formula (1-3) and compounds represented by formula (1-4), and the like.
- M 1 to M 5 each independently represent a metal atom.
- the compound Y is a compound in which a ligand is coordinated to a metal atom at a ratio of 1:3, a compound in which a ligand is coordinated to a metal atom at a ratio of 1:4, a metal atom
- a compound in which the ligand is coordinated to the metal atom in a ratio of 2:3 and a compound in which the ligand is coordinated to the metal atom in a ratio of 3:3 may be used.
- a part of the ligand may be dissociated from the metal atom, or a compound other than the ligand may be coordinated to the metal atom.
- 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
- the compound Y may be a pigment or a dye.
- the maximum absorption wavelength of compound Y is preferably in the wavelength range of 400 to 700 nm, more preferably in the wavelength range of 400 to 600 nm.
- raw materials that have been purified using activated carbon or silica gel may be used.
- adsorbents used for purification include activated carbon, silica gel, zeolite, synthetic adsorbents, and florisil. These materials are preferably used in the form of powder or pellets.
- a method of dissolving the raw material in an organic solvent or water and passing the solution through a filter-like adsorbent, or a method of adding the adsorbent to the solution and stirring the solution are suitable.
- the amount of adsorbent used in the purification process is preferably 0.01 to 10 parts by mass with respect to 1 part by mass of the raw material.
- Methanol, acetone, methyl ethyl ketone, acetonitrile, tetrahydrofuran, cyclopentanone, N-methyl-2-pyrrolidone, etc. are preferably used as the organic solvent for dissolving the raw material. After removing the adsorbent by filtration, the organic solvent is distilled off, and a refined raw material can be obtained by crystallization by adding a poor solvent.
- compound Y examples include compounds (Y-1) to (Y-44), compounds (yy-1) to (yy-4), (yy-11) to (yy- 20).
- the coloring agent contained in the coloring composition of the present invention may further contain a coloring agent other than compound Y above.
- Other coloring agents used in combination include chromatic coloring agents such as green coloring agents, red coloring agents, yellow coloring agents, purple coloring agents, blue coloring agents and orange coloring agents, and black coloring agents.
- the other coloring agent is preferably at least one selected from green coloring agents, red coloring agents and orange coloring agents, and more preferably at least one selected from green coloring agents and red coloring agents. , green colorant.
- Other coloring agents may be pigments or dyes, but are preferably pigments. When a pigment is used as the other colorant, the interaction between the pigment as the other colorant and the compound Y facilitates the promotion of association formation, making it possible to form a film with more excellent light resistance.
- red colorants examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds, which form films with more excellent light resistance.
- diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds are preferred, and diketopyrrolopyrrole compounds are more preferred, because they are easy to use.
- the red colorant is preferably a pigment.
- red colorants include C.I. I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48: 1, 48: 2, 48: 3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81: 3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, 297 and other red pigments.
- 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.
- 10-2019-0140741 anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140744, JP 2020 A perylene compound described in JP-A-079396, a diketopyrrolopyrrole compound described in paragraphs 0025 to 0041 of JP-A-2020-066702, and the like can also be used.
- a red colorant a compound having a structure in which an aromatic ring group in which a group having an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton is used.
- C.I. I. Pigment Red 122, 177, 254, 255, 264, 269 and 272 are preferred, C.I. I. Pigment Red 254, 264, 272 are more preferred, and C.I. I. Pigment Red 254, 264 are more preferred.
- green colorants examples include phthalocyanine compounds and squarylium compounds. Phthalocyanine compounds are preferred because they facilitate the formation of films with superior light resistance. Also, the green colorant is preferably a pigment.
- green colorants include C.I. I. Green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65 and 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.
- 106909027 the phthalocyanine compound having a phosphoric acid ester as a ligand described in WO 2012/102395, described in JP 2019-008014.
- the phthalocyanine compound, the phthalocyanine compound described in JP-A-2018-180023, the compound described in JP-A-2019-038958, the aluminum phthalocyanine compound described in JP-A-2020-070426, JP-A-2020-076995 Core-shell type dyes described in, diarylmethane compounds described in JP-A-2020-504758, and the like can also be used.
- C.I. I. Pigment Green 7, 36, 58, 62, 63 are preferred.
- orange colorants include C.I. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. of orange pigments.
- Yellow colorants include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds and perylene compounds. Specific examples of yellow colorants include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167,
- a nickel azobarbiturate complex having the following structure can also be used.
- X 1 to X 16 each independently represent a hydrogen atom or a halogen atom
- Z 1 represents an alkylene group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by formula (QP1) include compounds described in paragraph 0016 of Japanese Patent No. 6443711.
- Y 1 to Y 3 each independently represent a halogen atom.
- n and m are integers of 0 to 6; p is an integer of 0 to 5; (n+m) is 1 or more.
- Specific examples of the compound represented by formula (QP2) include compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
- purple colorants include C.I. I. Purple pigments such as Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, 61 are included.
- blue colorants include C.I. I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc. pigments.
- An aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue colorant.
- Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A-2012-247591 and paragraph number 0047 of JP-A-2011-157478.
- 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.
- black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred.
- bisbenzofuranone compounds include compounds described in Japanese Patent Application Publication No. 2010-534726, Japanese Patent Application Publication No. 2012-515233, Japanese Patent Application Publication No. 2012-515234, etc.
- "Irgaphor Black” manufactured by BASF Corporation Available examples include compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. I. Pigment Black 31, 32 and the like.
- the azomethine compound include compounds described in JP-A-01-170601, JP-A-02-034664, and the like.
- the pyrrolopyrrole-based pigment has a crystallite size of 140 ⁇ or less in the plane direction corresponding to the maximum peak in the X-ray diffraction pattern among the eight planes ( ⁇ 1 ⁇ 1 ⁇ 1) of the crystal lattice planes. It is also preferable to use a material. Further, the physical properties of the pyrrolopyrrole pigment are preferably set as described in paragraphs 0028 to 0073 of JP-A-2020-097744.
- the crystallite size obtained from the half width of the peak derived from any crystal face in the X-ray diffraction spectrum when CuK ⁇ rays of the pigment are used as the X-ray source is preferably 0.1 nm to 100 nm, and preferably 0.1 nm to 100 nm. It is more preferably 5 nm to 50 nm, still more preferably 1 nm to 30 nm, and particularly preferably 5 nm to 25 nm.
- 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 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.
- a colored composition is preferably used as a colored composition for forming an infrared transmission filter.
- 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.
- the content of the coloring agent in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 55% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and even more preferably 70% by mass or less.
- the content of compound Y in the colorant is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the coloring composition of the present invention is used as a coloring composition for forming green pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a green coloring agent.
- compound Y is preferably a yellow colorant.
- the content of compound Y is preferably 5 to 60 parts by mass with respect to 100 parts by mass of the green colorant.
- the lower limit is preferably 10 parts by mass or more, more preferably 15 parts by mass or more.
- the upper limit is preferably 50 parts by mass or less, more preferably 40 parts by mass or less.
- the coloring composition of the present invention is used as a coloring composition for forming red pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a red coloring agent.
- compound Y is preferably a yellow colorant.
- the content of compound Y is preferably 5 to 50 parts by mass with respect to 100 parts by mass of the red colorant.
- the lower limit is preferably 10 parts by mass or more, more preferably 15 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less.
- the content of the yellow coloring agent in the coloring agent is preferably 30% by mass or more, and is 40% by mass or more. is more preferable, and 50% by mass or more is even more preferable.
- compound Y is preferably a yellow colorant.
- the content of compound Y in the yellow colorant is preferably 20% by mass or more, more preferably 25% by mass or more, and even more preferably 30% by mass or more.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- 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 weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, more preferably 5000 or more.
- resins examples include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, and polyarylene resins.
- ether phosphine oxide resins polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, siloxane resins and the like.
- the resin described in the examples of International Publication No.
- the resin it is preferable to use a resin having an acid group.
- acid groups include carboxy groups, phosphoric acid groups, sulfo groups, and phenolic hydroxy groups.
- 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.
- the resin having an acid group preferably contains a repeating unit having an acid group on its side chain, and more preferably contains 5 to 70 mol % of repeating units having an acid group on its side chain in all repeating units of the resin.
- the upper limit of the content of repeating units having an acid group in a side chain is preferably 50 mol % or less, more preferably 30 mol % or less.
- the lower limit of the content of repeating units having an acid group in the side chain is preferably 10 mol % or more, more preferably 20 mol % or more.
- the coloring composition of the present invention also preferably contains a resin having a basic group.
- the resin having a basic group is preferably a resin containing a repeating unit having a basic group in its side chain. It is more preferably a polymer, and more preferably a block copolymer having a repeating unit having a basic group on its side chain and a repeating unit containing no basic group. Resins having basic groups can also be used as dispersants.
- the amine value of the resin having basic groups is preferably 5-300 mgKOH/g.
- the lower limit is preferably 10 mgKOH/g or more, more preferably 20 mgKOH/g or more.
- the upper limit is preferably 200 mgKOH/g or less, more preferably 100 mgKOH/g or less.
- resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (manufactured by BYK-Chemie), Solsperse 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 3309, 50500, 390500, 390500 56000, 7100 (manufactured by Nippon Lubrizol), Efka PX 4300, 4330, 4046, 4060, 4080 (manufactured by BASF) and the like.
- the resin having a basic group is a block copolymer (B) described in paragraph numbers 0063 to 0112 of JP-A-2014-219665, and described in paragraph numbers 0046-0076 of JP-A-2018-156021. It is also possible to use the block copolymer A1 described above and vinyl resins having basic groups described in paragraphs 0150 to 0153 of JP-A-2019-184763, the contents of which are incorporated herein.
- the coloring composition of the present invention preferably contains a resin having an acid group and a resin having a basic group. According to this aspect, the storage stability of the coloring composition can be further improved.
- a resin having an acid group and a resin having a basic group are used in combination, the content of the resin having a basic group is 20 to 500 parts by mass with respect to 100 parts by mass of the resin having an acid group. It is preferably from 30 to 300 parts by mass, and even more preferably from 50 to 200 parts by mass.
- the resin is derived from a monomer component containing a compound represented by the following formula (ED1) and/or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as an "ether dimer"). It is also preferable to use a resin containing a repeating unit that
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0-15.
- the number of carbon atoms in the alkylene group represented by R 21 and R 22 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, particularly 2 or 3.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
- Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
- Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- Examples of ethylenically unsaturated bond-containing groups include vinyl groups, styrene groups, (meth)allyl groups, and (meth)acryloyl groups.
- Examples of the cyclic ether group include an epoxy group and an oxetanyl group, with the epoxy group being preferred.
- the epoxy group may be a cycloaliphatic epoxy group.
- the alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
- 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.
- R E1 represents a hydrogen atom or an alkyl group, n represents 0 or 1, * represents a bond; in formula (e-2), ring A E1 represents an aliphatic hydrocarbon represents a ring, and * represents a bond.
- the number of carbon atoms in the alkyl group represented by R E1 is preferably 1 to 20, more preferably 1 to 10, still more preferably 1 to 5, and particularly preferably 1 to 3.
- the alkyl group represented by R E1 is preferably linear or branched, more preferably linear.
- R E1 is preferably a hydrogen atom.
- R 1 E1 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
- formula (e-1) is a group represented by formula (e-1a) below.
- the aliphatic hydrocarbon ring represented by ring A E1 in formula (e-2) may be a monocyclic aliphatic hydrocarbon ring or a condensed aliphatic hydrocarbon ring.
- the aliphatic hydrocarbon ring represented by Ring A E1 may have a crosslinked structure.
- a condensed aliphatic hydrocarbon ring is preferable because a film having excellent moisture resistance can be easily formed, and a condensed aliphatic hydrocarbon ring having a crosslinked structure is preferable.
- Specific examples of the aliphatic hydrocarbon ring represented by ring A E1 include the groups shown below, and the group represented by formula (e-2-3) and represented by formula (e-2-4) groups are preferred. In the following formulas, * represents a bond.
- repeating units having a cyclic ether group include repeating units represented by formula (A1).
- 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 divalent linking group represented by L a1 in formula (A1) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), —NH— , --SO--, --SO 2 --, --CO--, --O--, --COO--, --OCO--, --S-- and groups formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched. Moreover, the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
- the cyclic ether group represented by Z a1 in formula (A1) includes an epoxy group and an oxetanyl group, preferably an epoxy group. Further, the cyclic ether group represented by Z a1 is preferably a group represented by formula (e-1) or a group represented by formula (e-2), and a group represented by formula (e-2) It is more preferable that the group is
- 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 acid group of the repeating unit B-1 and the acid group protected by the protecting group of the repeating unit B-2 include a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphoric acid group. , phenolic hydroxy group or carboxy group, more preferably carboxy group.
- 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 represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring;
- Ar Y1 represents an aryl group
- R Y10 represents an alkyl group or an aryl group;
- R Y11 represents an alkyl group or an aryl 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.
- Examples of the ring formed by combining two of R Y1 to R Y3 include a monocyclic cycloalkyl group such as a cyclopentyl group and a cyclohexyl group, a norbornyl group, a tetracyclodecanyl group, a tetracyclododecanyl group, and an adamantyl group.
- a monocyclic cycloalkyl group having 5 to 6 carbon atoms is preferred.
- one of the ring-constituting methylene groups may be replaced with a heteroatom such as an oxygen atom or a heteroatom-containing group such as a carbonyl group.
- the number of carbon atoms in the alkyl groups represented by R Y4 to R Y6 in formula (Y2) is preferably 1-12, more preferably 1-6, and even more preferably 1-4.
- the alkyl group may be linear, branched, or cyclic, but preferably linear or branched. At least two of R Y4 to R Y6 in formula (Y2) are preferably methyl groups. In formula (Y2), two of R Y4 to R Y6 may combine to form a ring.
- the ring to be formed includes the ring described in formula (Y1).
- 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.
- R Y7 or R Y8 and R Y9 preferably combine to form a ring.
- one of R Y7 and R Y8 is preferably a hydrogen atom.
- Ar Y1 represents an aryl group
- R Y10 represents an alkyl group or an aryl group
- Ar Y1 and R Y10 may combine with each other to form a ring.
- 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.
- R Y10 is preferably an alkyl group.
- R Y11 represents an alkyl group or an aryl group, preferably an alkyl group.
- 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 protecting group is within the above range, a colored composition having excellent storage stability and excellent curability at low temperatures can be obtained.
- protecting groups include 1-methoxyethyl group, 1-ethoxyethyl group, 1-n-propoxyethyl group, 1-n-butoxyethyl group, 1-t-butoxyethyl group and 1-cyclopentyloxyethyl group.
- 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.
- repeating unit B-1 examples include repeating units represented by the following formula (B1). Further, repeating units B-2 include repeating units represented by the following formula (B2). Further, the repeating unit B-3 includes a repeating unit represented by the following formula (B3).
- X b1 represents a trivalent linking group
- L b1 represents a single bond or a divalent linking group
- Z b1 represents an acid group.
- X b2 represents a trivalent linking group
- L b2 represents a single bond or a divalent linking group
- 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.
- the trivalent linking group represented by X b1 in formula (B1), the trivalent linking group represented by X b2 in formula (B2) and the trivalent linking group represented by X b3 in formula (B3) are not particularly limited. do not have.
- poly(meth)acrylic linking group, polyalkyleneimine linking group, polyester linking group, polyurethane linking group, polyurea linking group, polyamide linking group, polyether linking group, polystyrene linking group, bisphenol -based linking group, novolak-based linking group and the like preferably poly(meth)acrylic-based linking group, polyether-based linking group, polyester-based linking group, bisphenol-based linking group and novolac-based linking group, poly(meth)acrylic System linking groups are more preferred.
- the divalent linking group represented by L b1 in formula (B1), the divalent linking group represented by L b2 in formula (B2) and the divalent linking group represented by L b3 in formula (B3) include an alkylene group ( alkylene group preferably having 1 to 12 carbon atoms), arylene group (preferably arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO -, -OCO-, -S- and groups formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched.
- the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
- the acid group represented by Z b1 in formula (B1) includes a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxy group, and a carboxy group. is more preferred.
- 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 of formula (B3) include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- the content of the unit B-1 in the resin having a cyclic ether group is 5 to 85 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 60 mol % or less, more preferably 40 mol % or less.
- the lower limit is preferably 8 mol% or more, more preferably 10 mol% or more.
- the content of the unit B-2 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.
- the resin having a cyclic ether group contains each of the repeating unit B-1 and the repeating unit B-2, the resin having a cyclic ether group contains 0 repeating units B-2 per 1 mol of the repeating units B-1. It preferably contains 4 to 3.2 mol, more preferably 0.8 to 2.8 mol, even more preferably 1.2 to 2.4 mol.
- 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.
- a resin having a cyclic ether group preferably further contains a repeating unit having an aromatic hydrocarbon ring.
- the aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the aromatic hydrocarbon ring may have a substituent.
- An alkyl group etc. are mentioned as a substituent.
- the content of the repeating unit having an aromatic hydrocarbon ring is 1 to 65 in all repeating units of the resin having a cyclic ether group.
- Mole % is preferred.
- 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.
- Repeating units having an aromatic hydrocarbon ring include repeating units derived from monofunctional polymerizable compounds having an aromatic hydrocarbon ring, such as vinyl toluene and benzyl (meth)acrylate.
- resins having a cyclic ether group include, for example, naphthalene-modified epoxy resins such as EPICLON HP5000 and EPICLON HP4032D (manufactured by DIC Corporation).
- naphthalene-modified epoxy resins such as EPICLON HP5000 and EPICLON HP4032D (manufactured by DIC Corporation).
- alkyldiphenol-type epoxy resins include EPICLON 820 (manufactured by DIC Corporation).
- jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, jER1010 (manufactured by Mitsubishi Chemical Corporation), EPICLON860, EPICLON1050, EPICLON1051, EPICLON1055 (and Co., Ltd.) and the like.
- Phenolic novolak type epoxy resins include jER152, jER154, jER157S70, jER157S65 (manufactured by Mitsubishi Chemical Corporation), EPICLON N-740, EPICLON N-770, EPICLON N-775 (manufactured by DIC Corporation), and the like. mentioned.
- EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, EPICLON N-695 (manufactured by DIC Corporation) as cresol novolak type epoxy resins , and EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.).
- ADEKA RESIN EP-4080S, EP-4085S, EP-4088S manufactured by ADEKA Corporation
- Celoxide 2021P Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE3150, EPOLEAD PB 3600, EPOLEAD PB 4700 (manufactured by Daicel Corporation), Denacol EX-212L, EX-214L, EX-216L, EX-321L, EX-850L (manufactured by Nagase ChemteX Corporation) and the like.
- resin Ac a resin having an aromatic carboxy group
- the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
- the aromatic carboxy group is preferably contained in the main chain of the repeating unit.
- an aromatic carboxy group is a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
- the number of carboxy groups bonded to the aromatic ring is preferably 1-4, more preferably 1-2.
- 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).
- Ar 1 represents a group containing an aromatic carboxyl group
- L 1 represents -COO- or -CONH-
- L 2 represents a divalent linking group
- 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.
- 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.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1) or a group represented by the following formula (Q-2).
- the group containing an aromatic carboxyl group represented by Ar 1 may have a crosslinkable group.
- the crosslinkable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, more preferably an ethylenically unsaturated bond-containing group.
- Specific examples of the group containing an aromatic carboxyl group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). and the like.
- n1 represents an integer of 1 to 4, preferably 1 or 2, more preferably 2.
- 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.
- 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.
- 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).
- * 1 represents the bonding position with L1.
- L 1 represents -COO- or -CONH-, preferably -COO-.
- the divalent linking group represented by L 2 in formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these A group obtained by combining two or more of
- 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.
- the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- An alkylene group and an arylene group may have a substituent. A hydroxy group etc.
- 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.
- the group containing an aromatic carboxyl group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and the preferred range is also the same.
- L 11 represents -COO- or -CONH-, preferably -COO-.
- the trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and 2 of these Groups in which more than one species are combined are included.
- Hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- the aliphatic hydrocarbon group may be linear, branched or cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, even more preferably 6-10.
- the hydrocarbon group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- the trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula (L12-2).
- L 12b 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 12b includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, and a hydrocarbon group or a group of a combination of a hydrocarbon group and —O— is preferred.
- 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.
- P 10 in formula (Ac-2) represents a polymer chain.
- the polymer chain represented by P10 preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
- the weight average molecular weight of the polymer chain P10 is preferably 500-20,000 .
- the lower limit is preferably 1000 or more.
- the upper limit is preferably 10,000 or less, more preferably 5,000 or less, even more preferably 3,000 or less. If the weight average molecular weight of P10 is within the above range, the dispersibility of the pigment in the composition is good.
- the resin having an aromatic carboxyl group is a resin having repeating units represented by formula (Ac-2), this resin is preferably used as a dispersant.
- the polymer chain represented by P10 may contain crosslinkable groups.
- Crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- the coloring composition of the present invention preferably contains a resin as a dispersant.
- Dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is greater than the amount of basic groups.
- the acidic dispersant (acidic resin) a resin having an acid group content of 70 mol % or more is preferable when the total amount of the acid group and the basic group is 100 mol %.
- the acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10-105 mgKOH/g.
- a basic dispersant represents a resin in which the amount of basic groups is greater than the amount of acid groups.
- a resin containing more than 50 mol % of basic groups is preferable when the total amount of acid groups and basic groups is 100 mol %.
- the basic group possessed by the basic dispersant is preferably an amino group.
- the resin used as the dispersant is also preferably a graft resin.
- graft resin for details of the graft resin, reference can be made to paragraphs 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein.
- 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 having a structure in which a plurality of polymer chains are bonded to the core.
- resins include, for example, dendrimers (including star polymers). Further, specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.
- 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. It is more preferably mol %.
- resins described in JP-A-2018-087939, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, Polyethyleneimine having a polyester side chain described in WO 2016/104803, block copolymer described in WO 2019/125940, block polymer having an acrylamide structural unit described in JP 2020-066687 , a block polymer having an acrylamide structural unit described in JP-A-2020-066688, a dispersant described in WO 2016/104803, and the like can also be used.
- Dispersants are also available as commercial products, and specific examples thereof include Disperbyk series manufactured by BYK-Chemie (e.g., Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajinomoto Fine-Techno Co., Inc. Ajisper series, and the like.
- Dispersants are also available as commercial products, and specific examples thereof include Disperbyk series manufactured by BYK-Chemie (e.g., Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajinomoto Fine-Techno Co., Inc. Ajisper series, and the like.
- the content of the resin in the total solid content of the coloring composition is preferably 1 to 50% by mass.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more.
- the coloring composition of the present invention may contain only one resin, or may contain two or more resins. When two or more resins are included, the total amount thereof is preferably within the above range.
- 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.
- the polymerizable compound may be in any chemical form such as monomer, prepolymer, oligomer, etc., but monomer is preferred.
- the molecular weight of the polymerizable compound is preferably 100-3000.
- the upper limit is preferably 2000 or less, more preferably 1500 or less.
- the lower limit is preferably 150 or more, more preferably 250 or more.
- the lower limit is preferably 3 mmol/g or more, more preferably 4 mmol/g or more, and even more preferably 5 mmol/g or more.
- the upper limit is preferably 12 mmol/g or less, more preferably 10 mmol/g or less, and even more preferably 8 mmol/g or less.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 4 or more ethylenically unsaturated bond-containing groups.
- the upper limit of the ethylenically unsaturated bond-containing groups is preferably 15 or less, more preferably 10 or less, even more preferably 6 or less, from the viewpoint of the stability of the colored composition over time.
- the polymerizable compound is preferably a tri- or more functional (meth) acrylate compound, more preferably a 3- to 15-functional (meth) acrylate compound, and a 3- to 10-functional (meth) acrylate compound. is more preferred, and tri- to hexa-functional (meth)acrylate compounds are particularly preferred.
- polymerizable compounds examples include dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and modified products of these compounds. mentioned.
- Modified compounds include compounds having a structure in which the (meth)acryloyl groups of the above compounds are bonded via an alkyleneoxy group, such as ethoxylated dipentaerythritol hexa(meth)acrylate. Specific examples include compounds represented by formula (Z-4) and compounds represented by formula (Z-5).
- E is each independently -((CH 2 ) y CH 2 O)- or -((CH 2 ) y CH(CH 3 )O)- , each y 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
- each m independently represents an integer of 0 to 10
- 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.
- 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.
- Polypentaerythritol poly(meth)acrylate represented by the following formula (Z-6) can also be used as the polymerizable compound.
- X 1 to X 6 each independently represent a hydrogen atom or a (meth)acryloyl group, and n represents an integer of 1-10. However, at least one of X 1 to X 6 is a (meth)acryloyl group.
- the polymerizable compound used in the present invention is at least one selected from the group consisting of dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, polypentaerythritol poly(meth)acrylate and modified products thereof. Seeds are preferred.
- Commercially available products include KAYARAD D-310, DPHA, DPEA-12 (manufactured by Nippon Kayaku Co., Ltd.), NK Ester A-DPH-12E, TPOA-50 (manufactured by Shin-Nakamura Chemical Co., Ltd.), etc. mentioned.
- 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.
- NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), Light acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate) and the like can also be used.
- trimethylolpropane tri(meth)acrylate trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, isocyanuric acid ethylene oxide-modified tri(meth)acrylate
- trifunctional (meth)acrylate compounds such as pentaerythritol tri(meth)acrylate.
- Commercial products of trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306 and M-305.
- M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
- a compound having an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group can be used as the polymerizable compound.
- Commercially available products of such compounds include Aronix M-305, M-510, M-520 and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- a compound having a caprolactone structure can also be used as the polymerizable compound.
- the descriptions in paragraphs 0042 to 0045 of JP-A-2013-253224 can be referred to, the contents of which are incorporated herein.
- Compounds having a caprolactone structure include, for example, DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available as KAYARAD DPCA series from Nippon Kayaku 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).
- the polymerizable compound it is also preferable to use a compound such as toluene that does not substantially contain environmentally regulated substances.
- a compound such as toluene that does not substantially contain environmentally regulated substances.
- Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- urethane acrylates such as those described in Japanese Patent Publication No. 48-041708, Japanese Patent Publication No. 51-037193, Japanese Patent Publication No. 02-032293, and Japanese Patent Publication No. 02-016765
- urethane compounds having an ethylene oxide skeleton described in JP-B-58-049860, JP-B-56-017654, JP-B-62-039417 and JP-B-62-039418.
- the polymerizable compound includes UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, Commercially available products such as T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.
- the content of the polymerizable compound in the total solid content of the coloring composition is preferably 1 to 35% by mass.
- the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more.
- the coloring composition of the present invention may contain only one polymerizable compound, or may contain two or more polymerizable compounds. When two or more polymerizable compounds are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a photopolymerization initiator.
- 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.
- photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
- acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- photopolymerization initiators include trihalomethyltriazine compounds, 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.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (above company) and the like.
- ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by Irgacure 369E, Irgacure 379EG). made), etc.
- acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819 and Irgacure TPO (manufactured by BASF).
- Examples of oxime compounds include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, J. Am. C. S. Compounds described in Perkin II (1979, pp.1653-1660); C. S. Compounds described in Perkin II (1979, pp.156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp.202-232), compounds described in JP-A-2000-066385, Compounds described in JP-A-2004-534797, compounds described in JP-A-2006-342166, compounds described in JP-A-2017-019766, compounds described in Patent No. 6065596, International Publication No.
- oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropane-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(
- An oxime compound having a fluorene ring can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorene ring include compounds described in JP-A-2014-137466, compounds described in Japanese Patent No. 6636081, and compounds described in Korean Patent Publication No. 10-2016-0109444. mentioned.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such oxime compounds include compounds described in WO2013/083505.
- An oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom include compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. and the compound (C-3) of.
- An oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraph numbers 0031 to 0047 of JP-A-2013-114249 and paragraph numbers 0008-0012 and 0070-0079 of JP-A-2014-137466; Compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 and ADEKA Arkles NCI-831 (manufactured by ADEKA Corporation) can be mentioned.
- An oxime compound having a benzofuran skeleton can also be used as the photopolymerization initiator.
- Specific examples include OE-01 to OE-75 described in WO 2015/036910.
- an oxime compound in which a substituent having a hydroxyl group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- an oxime compound having an aromatic ring group Ar 2 OX1 in which an electron-withdrawing group is introduced into the aromatic ring (hereinafter also referred to as oxime compound OX) can be used.
- the electron-withdrawing group possessed by the aromatic ring group Ar OX1 include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group.
- 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.
- 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), and more preferably the compound represented by the formula (OX2). preferable.
- R X1 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 a group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphinoyl group, a carbamoyl group or a sulfamoyl group
- R X2 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group
- electron-withdrawing groups include acyl groups, nitro groups, trifluoromethyl groups, alkylsulfinyl groups, arylsulfinyl groups, alkylsulfonyl groups, arylsulfonyl groups, and cyano groups, with acyl groups and nitro groups being preferred.
- An acyl group is more preferred, and a benzoyl group is even more preferred, because a film having excellent properties can be easily formed.
- R X12 is an electron-withdrawing group
- R X10 , R X11 , R X13 and R X14 are preferably hydrogen atoms.
- oxime compound OX examples include compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited to these.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300000, even more preferably 2000 to 300000, even more preferably 5000 to 200000, from the viewpoint of sensitivity. It is particularly preferred to have
- the molar extinction coefficient of a compound can be measured using known methods. For example, it is preferably measured at a concentration of 0.01 g/L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- the photopolymerization initiator it is also preferable to use a combination of Irgacure OXE01 (manufactured by BASF) and/or Irgacure OXE02 (manufactured by BASF) and Omnirad 2959 (manufactured by IGM Resins B.V.).
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so good sensitivity can be obtained.
- the crystallinity is reduced, the solubility in a solvent or the like is improved, the precipitation becomes difficult over time, and the stability over time of the colored composition can be improved.
- Specific examples of bifunctional or trifunctional or higher photoradical polymerization initiators include Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
- the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less.
- only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
- 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.
- Ester-based solvents substituted with cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups can also be preferably used.
- organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) 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 organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one isomer may be contained, or a plurality of isomers may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the coloring composition is preferably 10-95% by mass, more preferably 20-90% by mass, and even more preferably 30-90% by mass.
- 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.
- distillation off a small amount of environmentally regulated substances it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to increase the efficiency.
- a polymerization inhibitor or the like is added and distilled off under reduced pressure in order to suppress the radical polymerization reaction from progressing during the vacuum distillation and the intermolecular cross-linking.
- These distillation methods are the raw material stage, the reaction product of the raw materials (for example, the resin solution or polyfunctional monomer solution after polymerization), or the colored composition stage produced by mixing these compounds. It is possible at any stage such as
- the coloring composition of the present invention can further contain an infrared absorbing agent.
- 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 light to be transmitted through the film obtained by containing an infrared absorbing agent in the coloring composition is shifted to a longer wavelength side.
- 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 wavelength range of more than 700 nm and 1800 nm or less.
- 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.
- infrared absorbers examples include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, and azomethine. compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like.
- pyrrolopyrrole compound compounds described in paragraph numbers 0016 to 0058 of JP-A-2009-263614, compounds described in paragraph numbers 0037-0052 of JP-A-2011-068731, WO 2015/166873 Compounds described in Paragraph Nos. 0010 to 0033 and the like.
- examples of the squarylium compound include compounds described in paragraph numbers 0044 to 0049 of JP-A-2011-208101, compounds described in paragraph numbers 0060 to 0061 of Japanese Patent No. 6065169, and paragraph number 0040 of WO 2016/181987.
- cyanine compound compounds described in paragraph numbers 0044 to 0045 of JP-A-2009-108267, compounds described in paragraph numbers 0026-0030 of JP-A-2002-194040, described in JP-A-2015-172004
- Examples of croconium compounds include compounds described in JP-A-2017-082029.
- the iminium compound for example, compounds described in JP-A-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, International Publication No. 2018/043564 and the compounds described in paragraphs 0048 to 0063 of.
- the phthalocyanine compound include compounds described in paragraph number 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, and paragraph numbers 0013 to 0029 of JP-A-2013-195480.
- naphthalocyanine compounds include compounds described in paragraph number 0093 of JP-A-2012-077153.
- Dithiolene metal complexes include compounds described in Japanese Patent No. 5733804.
- metal oxides include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- metal borides include lanthanum boride.
- 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.
- commercial products of indium tin oxide include F-ITO (manufactured by DOWA Hi-Tech Co., Ltd.).
- the infrared absorbing agent the squarylium compound described in JP-A-2017-197437, the squarylium compound described in JP-A-2017-025311, the squarylium compound described in WO 2016/154782, and the patent No. 5884953. No. 6036689, squarylium compounds described in Japanese Patent No. 5810604, squarylium compounds described in paragraphs 0090 to 0107 of International Publication No.
- the content of the infrared absorbing agent in the total solid content of the coloring composition is preferably 1 to 40% by mass.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less.
- the coloring composition of the present invention may contain only one type of infrared absorbing agent, or may contain two or more types thereof. When two or more kinds of infrared absorbing agents are included, the total amount thereof is preferably within the above range.
- 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.
- dye skeletons constituting pigment derivatives include a quinoline dye skeleton, a benzimidazolone dye skeleton, a benzoisoindole dye skeleton, a benzothiazole dye skeleton, an iminium dye skeleton, a squarylium dye skeleton, a croconium dye skeleton, an oxonol dye skeleton, and a pyrrolopyrrole dye.
- diketopyrrolopyrrole dye skeleton azo dye skeleton, azomethine dye skeleton, phthalocyanine dye skeleton, naphthalocyanine dye skeleton, anthraquinone dye skeleton, quinacridone dye skeleton, dioxazine dye skeleton, perinone dye skeleton, perylene dye skeleton, thioindigo dye skeleton, Isoindoline dye skeletons, isoindolinone dye skeletons, quinophthalone dye skeletons, iminium dye skeletons, dithiol dye skeletons, triarylmethane dye skeletons, pyrromethene dye skeletons, and the like can be mentioned.
- the acid group includes a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imidic acid group and salts thereof.
- Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ion and the like.
- the carboxylic acid amide group a group represented by —NHCOR X1 is preferable.
- sulfonic acid amide group a group represented by —NHSO 2 R X2 is preferable.
- the imidic acid group is preferably a group represented by —SO 2 NHSO 2 R X3 , —CONHSO 2 R X4 , —CONHCOR X5 or —SO 2 NHCOR X6 , more preferably —SO 2 NHSO 2 R X3 .
- R X1 to R X6 each independently represent an alkyl group or an aryl group.
- the alkyl groups and aryl groups represented by R X1 to R X6 may have substituents.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Basic groups include amino groups, pyridinyl groups and salts thereof, salts of ammonium groups, and phthalimidomethyl groups.
- Atoms or atomic groups constituting salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
- a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) can also be used as the pigment derivative.
- the maximum value ( ⁇ max) of the molar extinction coefficient of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less, and 1000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less. is more preferable, and 100 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less is even more preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more, and may be 10 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more.
- pigment derivatives include the compounds described in the examples described later, JP-A-56-118462, JP-A-63-264674, JP-A-01-217077, and JP-A-03-009961. , JP-A-03-026767, JP-A-03-153780, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, Patent JP-A-06-240158, JP-A-10-030063, JP-A-10-195326, paragraph numbers 0086 to 0098 of WO 2011/024896, paragraph numbers 0063 to 0094 of WO 2012/102399 , Paragraph No.
- 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.
- 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.
- a polyalkyleneimine is a polymer having a branched structure each containing a primary amino group, a secondary amino group, and a tertiary amino group.
- the alkyleneimine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, still more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.
- the molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more.
- the upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less.
- the molecular weight of the polyalkyleneimine when the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkyleneimine is the value calculated from the structural formula.
- the molecular weight of the specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used.
- 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.
- the amine value of the polyalkyleneimine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
- 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.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- 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.
- UV absorber examples 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).
- the ultraviolet absorber is a compound described in paragraph numbers 0049 to 0059 of Japanese Patent No.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- only one ultraviolet absorber may be used, or two or more ultraviolet absorbers may be used.
- the total amount is preferably within the above range.
- 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.
- the coloring composition of the present invention can contain a silane coupling agent.
- a silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- 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.
- silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), ⁇ -aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM
- silane coupling agent examples 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 type of silane coupling agent may be used, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.
- the coloring composition of the present invention can contain a surfactant.
- a 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.
- surfactants reference can be made to surfactants described in paragraphs 0238-0245 of WO2015/166779, the contents of which are incorporated herein.
- the fluorine content in the fluorine-based surfactant is preferably 3-40% by mass, more preferably 5-30% by mass, and particularly preferably 7-25% by mass.
- a fluorosurfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and saving liquid, and has good solubility in the coloring composition.
- JP 2014-041318 Paragraph Nos. 0060 to 0064 (corresponding International Publication No. 2014/017669 Paragraph Nos. 0060 to 0064) surfactants described in, JP 2011- Examples include surfactants described in paragraphs 0117 to 0132 of JP-A-132503 and surfactants described in JP-A-2020-008634, the contents of which are incorporated herein.
- Commercially available fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143 and F-144.
- the fluorosurfactant has a molecular structure with a functional group containing a fluorine atom, and an acrylic compound in which the functional group containing a fluorine atom is cleaved and the fluorine atom volatilizes when heat is applied is also suitable.
- fluorine-based surfactants include MegaFac DS series manufactured by DIC Corporation (Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega Fac DS-21.
- fluorosurfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorosurfactant.
- fluorosurfactants include fluorosurfactants described in JP-A-2016-216602, the contents of which are incorporated herein.
- a block polymer can also be used as the fluorosurfactant.
- the fluorosurfactant has a repeating unit derived from a (meth)acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (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.
- a fluorine-containing imide salt compound represented by formula (fi-1) is also preferable to use as a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a+ is a valent metal ion, primary ammonium ion, Represents secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH 4 + .
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF company), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Nippon Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (Fuji
- Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK-Chemie) and the like.
- a compound having the following structure can also be used as the silicone-based surfactant.
- the content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% by mass to 3.0% by mass. Only one type of surfactant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.
- 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.
- 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.
- 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 paragraph numbers 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.
- 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.
- auxiliaries e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.
- the coloring composition of the present invention may contain a latent antioxidant, if desired.
- 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.
- a compound that functions as an antioxidant by removing the protective group by the reaction is exemplified.
- 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.).
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
- metal oxides include TiO 2 , ZrO 2 , Al 2 O 3 and SiO 2 .
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, even more preferably 5 to 50 nm.
- Metal oxides may have a core-shell structure. Moreover, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improver.
- a light resistance improver compounds described in paragraph numbers 0036 to 0037 of JP-A-2017-198787, compounds described in paragraph numbers 0029-0034 of JP-A-2017-146350, JP-A-2017-129774 Compounds described in paragraph numbers 0036 to 0037, 0049 to 0052 of JP 2017-129674 JP 2017-129674 paragraph numbers 0031 to 0034, 0058 to 0059 compounds described in JP 2017-122803 paragraph numbers 0036 to 0037 , compounds described in 0051 to 0054, compounds described in paragraph numbers 0025 to 0039 of WO 2017/164127, compounds described in paragraph numbers 0034 to 0047 of JP 2017-186546, JP 2015-025116 Compounds described in paragraph numbers 0019 to 0041 of JP-A-2012-145604, compounds described in paragraph numbers 0101-0125 of JP-A-2012-103475, compounds
- the coloring composition of the present invention preferably does not substantially contain terephthalic acid ester.
- substantially free means that the content of terephthalic acid ester is 1000 mass ppb or less in the total amount of the coloring composition, and more preferably 100 mass ppb or less, Zero is particularly preferred.
- perfluoroalkylsulfonic acid and its salts may be regulated.
- perfluoroalkylsulfonic acid especially perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- fluoroalkylcarboxylic acid especially perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- its salt is 0.01ppb to 1,000ppb with respect to the total solid content of the coloring composition.
- the coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts.
- a compound that can substitute for perfluoroalkylsulfonic acid and its salt and a compound that can substitute for perfluoroalkylcarboxylic acid and its salt, perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and salts thereof may be selected.
- Examples of compounds that can substitute for regulated compounds include compounds that are excluded from the scope of regulation due to differences in the number of carbon atoms in perfluoroalkyl groups. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
- the coloring composition of the present invention may contain perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts within the maximum permissible range.
- 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 coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface state (flatness, etc.) and adjusting the film thickness.
- the viscosity value can be appropriately selected as necessary, and is preferably, for example, 0.3 mPa ⁇ s to 50 mPa ⁇ s, more preferably 0.5 mPa ⁇ s to 20 mPa ⁇ s at 25°C.
- a method for measuring the viscosity for example, a cone-plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25°C.
- the storage container for the coloring composition is not particularly limited, and known storage containers can be used.
- 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.
- 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.
- the coloring composition of the present invention can be prepared by mixing the aforementioned ingredients.
- 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.
- a process of dispersing the pigment when preparing the coloring composition.
- mechanical forces used for dispersing pigments include compression, squeezing, impact, shearing, cavitation, and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion, and the like.
- 2015-157893 can be suitably used.
- the particles may be made finer in the salt milling process.
- Materials, equipment, processing conditions, etc. used in the salt milling step can be referred to, for example, Japanese Patent Application Laid-Open Nos. 2015-194521 and 2012-046629.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF)
- polyamide resins such as nylon (eg nylon-6, nylon-6,6)
- polyolefin resins such as polyethylene and polypropylene (PP) (including high-density, ultra-high-molecular-weight polyolefin resin) and other materials.
- PP polypropylene
- nylon including high density polypropylene
- nylon including high density polypropylene
- 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. .
- fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers.
- Commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Roki Techno.
- filters When using filters, different filters (eg, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed twice or more. Also, filters with different pore sizes within the range described above may be combined. Alternatively, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing other components, the filtration with the second filter may be performed. In addition, the filter can be appropriately selected according to the hydrophilicity/hydrophobicity of the composition.
- the film of the present invention is a film obtained from the coloring composition of the present invention described above.
- the film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
- the film of the present invention When the film of the present invention is used as a color filter, the film of the present invention preferably has a hue of green, red, blue, cyan, magenta or yellow, and more preferably has a hue of green, red or yellow. preferable. Moreover, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Red pixels, green pixels, and yellow pixels are preferred, and red pixels or green pixels are preferred. is more preferable, and green pixels are even more preferable.
- 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.
- the wavelength on the long wavelength side at which the light transmittance is 50% preferably exists in the wavelength range of 580 to 620 nm, more preferably in the wavelength range of 585 to 615 nm.
- a film having such spectral characteristics is preferably used as a green pixel.
- the film of the present invention preferably has, for example, any one of the following spectral characteristics (1) to (4).
- 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.
- 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 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.
- 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 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.
- 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 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.
- the film of the present invention can be produced through the step of applying the coloring composition of the present invention.
- 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.
- 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 colored composition layer of the present invention is used to form the colored composition layer on the support.
- the support is not particularly limited and can be appropriately selected depending on the application. Examples thereof include glass substrates and silicon substrates, and silicon substrates are preferred. Also, a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CCD charge-coupled device
- CMOS complementary metal oxide semiconductor
- the silicon substrate is formed with a black matrix that isolates each pixel.
- the silicon substrate may be provided with an underlying layer for improving adhesion with the upper layer, preventing diffusion of substances, or flattening the substrate surface.
- 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 resin, polymerizable compound, surfactant, etc. described herein. good.
- 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.
- a known method can be used as a method for applying the coloring composition.
- dropping method drop cast
- slit coating method spray method
- roll coating method spin coating
- methods described in publications inkjet
- ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc.
- Examples include various printing methods; transfer methods using molds and the like; nanoimprinting methods and the like.
- the application method for inkjet is not particularly limited.
- 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.
- Radiation (light) that can be used for exposure includes g-line, i-line, and the like.
- Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
- Light having a wavelength of 300 nm or less includes KrF rays (wavelength: 248 nm), ArF rays (wavelength: 193 nm), etc., and KrF rays (wavelength: 248 nm) are preferred.
- a long-wave light source of 300 nm or more can also be used.
- the light when exposing, the light may be continuously irradiated and exposed, or may be irradiated and exposed in a pulsed manner (pulse exposure).
- pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and rest in short-time (for example, millisecond level or less) cycles.
- 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 unexposed areas of the colored composition layer are removed by development to form a pattern (pixels).
- the development and removal of the unexposed portion of the colored composition layer can be performed using a developer.
- the unexposed portion of the colored composition layer in the exposure step is eluted into the developer, leaving only the photocured portion.
- the temperature of the developer is preferably 20 to 30° C., for example.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the step of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
- the developer includes an organic solvent, an alkaline developer, etc., and an alkaline developer is preferably used.
- an alkaline developer an alkaline aqueous solution (alkali developer) obtained by diluting an alkaline agent with pure water is preferable.
- alkaline agents include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- ethyltrimethylammonium hydroxide ethyltrimethylammonium hydroxide
- benzyltrimethylammonium hydroxide dimethylbis(2-hydroxyethyl)ammonium hydroxide
- choline pyrrole
- piperidine 1,8-diazabicyclo-[5.4.0]-7-undecene
- examples include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate and sodium metasilicate.
- a compound having a large molecular weight is preferable for the alkaline agent from the standpoint of environment and safety.
- 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 rinse solution to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- the nozzle for discharging the rinsing liquid from the central portion of the support to the peripheral portion of the support.
- the moving speed of the nozzle may be gradually decreased.
- Additional exposure processing and post-baking are post-development curing treatments for complete curing.
- the heating temperature in post-baking is, for example, preferably 100 to 240.degree. C., more preferably 200 to 240.degree.
- Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulating dryer), or a high-frequency heater so that the developed film satisfies the above conditions. .
- the light used for exposure preferably has a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by a dry etching method is a step of forming a colored composition layer on a support using the colored composition of the present invention, and curing the entire colored composition layer to form a cured product layer; a step of forming a photoresist layer on the cured layer; a step of patternwise exposing the photoresist layer and then developing it to form a resist pattern; and etching the cured layer using the resist pattern as a mask. and dry etching using a gas.
- a mode in which heat treatment after exposure and heat treatment (post-baking treatment) after development are performed is desirable.
- pattern formation by a dry etching method descriptions in paragraphs 0010 to 0067 of JP-A-2013-064993 can be referred to, and the contents thereof are incorporated herein.
- 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 optical filter may have a protective layer on the surface of the film of the present invention.
- a protective layer By providing the protective layer, it is possible to impart various functions such as blocking oxygen, reducing reflection, making the film hydrophilic and hydrophobic, and blocking light of a specific wavelength (ultraviolet rays, near-infrared rays, etc.).
- the thickness of the protective layer is preferably 0.01-10 ⁇ m, more preferably 0.1-5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of bonding a molded resin with an adhesive.
- Components constituting the protective layer include (meth)acrylic resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, and polyimides.
- the protective layer preferably contains a polyol resin, SiO 2 and Si 2 N 4 .
- the protective layer preferably contains a (meth)acrylic resin and a fluororesin.
- a resin composition When a resin composition is applied to form a protective layer, known methods such as spin coating, casting, screen printing, and ink-jetting can be used as methods for applying the resin composition.
- Known organic solvents eg, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method includes known chemical vapor deposition methods (thermal chemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). can be used.
- the protective layer contains organic/inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index modifiers, antioxidants, adhesion agents, additives such as surfactants. may contain.
- organic/inorganic fine particles include polymeric fine particles (eg, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, and the like.
- a known absorber can be used as the absorber for light of a specific wavelength.
- the content of these additives can be appropriately adjusted, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer.
- the protective layer the protective layers described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- 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.
- a plurality of photodiodes and transfer electrodes made of polysilicon or the like are provided on the substrate, forming the light-receiving area of a solid-state imaging device (CCD (charge-coupled device) image sensor, CMOS (complementary metal-oxide semiconductor) image sensor, etc.). and a device protective film made of silicon nitride or the like formed on the light shielding film so as to cover the entire surface of the light shielding film and the photodiode light receiving portion. and a color filter on the device protective film.
- CCD charge-coupled device
- CMOS complementary metal-oxide semiconductor
- the color filter may have a structure in which each color pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each color pixel. Examples of imaging devices having such a structure include devices described in JP-A-2012-227478, JP-A-2014-179577, and International Publication No. 2018/043654.
- an ultraviolet absorption layer may be provided in the structure of the solid-state imaging device to improve light resistance.
- An imaging device equipped with the solid-state imaging device of the present invention can be used not only for digital cameras and electronic devices having an imaging function (mobile phones, etc.), but also for vehicle-mounted cameras and monitoring cameras.
- the image display device of the present invention has the film of the present invention described above.
- image display devices include liquid crystal display devices and organic electroluminescence display devices.
- 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).
- the present invention can be applied to liquid crystal display devices of various systems described in the above “next generation liquid crystal display technology”.
- Compounds (Y-28) to (Y-34) and compounds (Y-40) to (Y-44) are compounds in which the zinc atom is coordinated with the compounds listed in the column for compound S in the table below. .
- the maximum absorption wavelengths of compounds (Y-28) to (Y-34) and compounds (Y-40) to (Y-44) were in the wavelength range of 400 to 600 nm.
- 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.) with a pressure reduction 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.
- the amounts of colorants 1 to 4, infrared absorbers, pigment derivatives and dispersants are values in terms of solid content.
- Y-1 to Y-44 Compounds Y-1 to Y-44 described above Yb-1: compound having the following structure (C.I. Pigment Yellow 129) yy-1 to yy-4: compounds having the following structures yy-11 to yy-20: compounds having the following structures PG36: C.I. I. Pigment Green 36 (phthalocyanine compound, green pigment) 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 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)
- IR-1 a compound having the following structure
- 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)
- B-2 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: 10,000)
- B-3 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 7000) B-7 Resin synthesized by the following method An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, the atmosphere was replaced with nitrogen, and 340 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) was added. and heated to 80° C. with stirring.
- PGMEA propylene glycol monomethyl ether acetate
- the obtained resin had a weight average molecular weight of 9400, a dispersity of 1.89 and an acid value of 114 mgKOH/g.
- a coloring composition was produced by mixing the raw materials shown in the table below.
- the content of compound Y in the total solid content of the coloring composition is also shown in the column of content of compound Y in the table below.
- Dispersions 1 to 133 Dispersions 1 to 133 described above, Comparative Dispersions 1 and 2
- 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)
- C-2 Resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 30,000)
- C-3 Resin having the following structure (values attached to the main chain are mass ratios. Weight average molecular weight: 14,600)
- C-4 Resin having the following structure (values attached to the main chain are mass ratios.
- Weight average molecular weight: 10,600) C-5 Resin synthesized by the following method A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, and 371 parts by mass of 1-methoxy-2-propyl acetate was added. was heated to 85° C. with stirring. Next, 54 parts by mass of acrylic acid, 225 parts by mass of a mixture of 3,4-epoxytricyclo[5.2.1.02,6]decane-8 and 9-yl acrylate, and 81 parts by mass of vinyl toluene (isomer mixture) , and 80 parts by mass of 1-methoxy-2-propyl acetate was added dropwise over 4 hours.
- a solution prepared by dissolving 30 parts by mass of 2,2-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator in 160 parts by mass of 1-methoxy-2-propyl acetate was added dropwise over 5 hours. After the completion of the dropwise addition of the initiator solution, the temperature was maintained at 85° C. for 4 hours, and then cooled to room temperature to obtain a resin.
- the obtained resin had a weight average molecular weight of 10,600, a dispersity of 2.01, and an acid value of 43 mgKOH/g.
- D-1 A compound having the following structure
- D-2 A mixture of compounds having the following structure (a mixture in which the molar ratio of the left compound (hexafunctional (meth)acrylate compound) and the right compound (pentafunctional (meth)acrylate compound) is 7:3)
- D-3 A compound having the following structure
- D-4 Trimethylolpropane ethylene oxide-modified triacrylate (manufactured by Toagosei Co., Ltd., Aronix M-350)
- D-5 EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
- D-6 ethoxylated dipentaerythritol hexamethacrylate
- 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 (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 %.
- F-3 Futergent 208G (manufactured by NEOS, fluorosurfactant)
- 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 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 of 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.
- 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.
- 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%.
- the colored compositions of Examples were able to form films with excellent light resistance. Furthermore, the colored compositions of Examples were also excellent in storage stability. Optical filters, solid-state imaging devices, and image display devices with excellent light resistance can be obtained by using the films obtained from the colored compositions of Examples.
- Example 1001 1 part by mass of compound (a-1), 8 parts by mass of acetone, and 0.3 parts by mass of activated carbon (manufactured by Osaka Gas Chemicals Co., Ltd.) were added and stirred for 10 minutes. After the activated carbon was separated by filtration using celite, it was concentrated and crystallized by adding 6 parts by mass of water. After filtering off the produced solid, it was washed with 5 parts by mass of water. The resulting solid was air-dried at 50° C. to obtain 0.9 parts by mass of compound (a-1a), which is a purified product of compound (a-1).
- Compound (Y-1a) was synthesized by using compound (a-1a) in place of compound (a-1) in Synthesis Example 1.
- Dispersion 1a was prepared in the same manner as in Dispersion 1 except that Compound (Y-1a) was used instead of Compound (Y-1).
- a coloring composition of Example 1001 was produced in the same manner as in Example 1, except that Dispersion 1a was used instead of Dispersion 1.
- the light resistance and storage stability were evaluated in the same manner as described above.
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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を含み、
上記着色組成物の全固形分中における上記化合物Yの含有量が10質量%以上である、着色組成物;
R2~R11はそれぞれ独立して水素原子または置換基を表し、
R2~R11のうち、隣接する2つは結合して環を形成していてもよい;
ただし、R2~R11の少なくとも1つは置換基である。
<2> 上記式(1)のR2~R11の少なくとも1つは、ヘテロ原子を含む官能基である、<1>に記載の着色組成物。
<3> 上記式(1)のR2~R11の少なくとも1つは、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>に記載の着色組成物。
<4> 上記金属原子が、銅原子または亜鉛原子である、<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、銅原子である、<1>~<3>のいずれか1つに記載の着色組成物。
<6> 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>~<5>のいずれか1つに記載の着色組成物。
<7> 上記着色剤は、更に、緑色着色剤を含む、<1>~<6>のいずれか1つに記載の着色組成物。
<8> 更に、重合性化合物と光重合開始剤を含む、<1>~<7>のいずれか1つに記載の着色組成物。
<9> 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>~<8>のいずれか1つに記載の着色組成物。
<10> <1>~<9>のいずれか1つに記載の着色組成物から得られる膜。
<11> <10>に記載の膜を有する光学フィルタ。
<12> <10>に記載の膜を有する固体撮像素子。
<13> <10>に記載の膜を有する画像表示装置。
<14> 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;
R2~R11はそれぞれ独立して水素原子または置換基を表し、
R2~R11のうち、隣接する2つは結合して環を形成していてもよい;
ただし、R2~R11の少なくとも1つはニトロ基、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。
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化合物を意味する。
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。
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を含み、上記着色組成物の全固形分中における上記化合物Yの含有量が10質量%以上であることを特徴とする。
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。着色組成物の全固形分中における化合物Yの含有量は、10質量%以上であり、10~40質量%であることが好ましく、10~35質量%であることがより好ましく、10~30質量%以下であることが更に好ましい。
R2~R11はそれぞれ独立して水素原子または置換基を表し、
R2~R11のうち、隣接する2つは結合して環を形成していてもよい;
ただし、R2~R11の少なくとも1つは置換基である。
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。
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。
R101とR102は結合して環を形成していてもよい。R101とR102が結合して形成される環としては、ピロリジン環、ピペリジン環、ピペラジン環、モルホリン環などが挙げられる。
また、式(1)のR2~R11のうち1~4個(より好ましくは1または2つ、更に好ましくは1つ)が置換基であることが好ましく、ヘテロ原子を含む基であることが好ましく、上述した特定官能基Aであることがより好ましい。
また、より耐光性に優れた膜を形成することができるという理由から、式(1)のR3、R4、R5、R6、R9およびR10の少なくとも1つ(好ましくは、R9およびR10の少なくとも1つ、より好ましくはR9)は置換基であることが好ましく、ヘテロ原子を含む基であることが好ましく、上述した特定官能基Aであることがより好ましい。なかでも、より耐光性に優れた膜を形成することができるという理由から、式(1)のR3、R4、R5、R6、R9およびR10の少なくとも1つ(好ましくは、R9およびR10の少なくとも1つ、より好ましくはR9)がヘテロ原子を含む基(好ましくは上述した特定官能基A)であり、残りが水素原子であることが好ましい。
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。
(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。
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。
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)
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。
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。
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。
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。
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。
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。
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。
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。
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。
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)。
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。
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。
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。
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。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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
(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。
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。
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。
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。
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。
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-27)を合成した。化合物(Y-2)~化合物(Y-27)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-27)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(Y-17)においてには、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。
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-28)~化合物(Y-34)、化合物(Y-40)~化合物(Y-44)を合成した。化合物(Y-28)~化合物(Y-34)、化合物(Y-40)~化合物(Y-44)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-28)~化合物(Y-34)、化合物(Y-40)~化合物(Y-44)の極大吸収波長は波長400~600nmの範囲に存在していた。
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-35)~化合物(Y-39)を合成した。化合物(Y-35)~化合物(Y-39)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-35)~化合物(Y-39)の極大吸収波長は波長400~600nmの範囲に存在していた。
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。
Y-1~Y-44:上述した化合物Y-1~Y-44
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)
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。
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)
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。下記表の化合物Yの含有量の欄に、着色組成物の全固形分中における化合物Yの含有量を合わせて記す。
分散液1~133、比較分散液1、2:上述した分散液1~133、比較分散液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。
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
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)
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)
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
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。
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。
化合物(a-1)1質量部、アセトン8質量部、活性炭(大阪ガスケミカル社製)0.3質量部を加え、10分間撹拌した。活性炭をセライトを用いて濾別後、濃縮し6質量部の水を加え晶析した。生成した固体を濾別した後に5質量部の水で洗浄した。得られた固体を50℃で送風乾燥し、化合物(a-1)の精製物である化合物(a-1a)を0.9質量部得た。合成例1において、化合物(a-1)の代わりに化合物(a-1a)を用いて、化合物(Y-1a)を合成した。
分散液1において、化合物(Y-1)のかわりに化合物(Y-1a)を用いた以外は同様にして分散液1aを製造した。
実施例1において、分散液1のかわりに、分散液1aを用いた以外は同様にして実施例1001の着色組成物を製造した。
実施例1001の着色組成物を用いて上記と同様の方法で耐光性および保存安定性を評価したところ、実施例1と同様の評価結果であった。
Claims (14)
- 前記式(1)のR2~R11の少なくとも1つは、ヘテロ原子を含む官能基である、請求項1に記載の着色組成物。
- 前記式(1)のR2~R11の少なくとも1つは、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に記載の着色組成物。 - 前記金属原子が、銅原子または亜鉛原子である、請求項1~3のいずれか1項に記載の着色組成物。
- 前記金属原子が、銅原子である、請求項1~3のいずれか1項に記載の着色組成物。
- 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1~5のいずれか1項に記載の着色組成物。
- 前記着色剤は、更に、緑色着色剤を含む、請求項1~6のいずれか1項に記載の着色組成物。
- 更に、重合性化合物と光重合開始剤を含む、請求項1~7のいずれか1項に記載の着色組成物。
- 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1~8のいずれか1項に記載の着色組成物。
- 請求項1~9のいずれか1項に記載の着色組成物から得られる膜。
- 請求項10に記載の膜を有する光学フィルタ。
- 請求項10に記載の膜を有する固体撮像素子。
- 請求項10に記載の膜を有する画像表示装置。
- 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;
R2~R11はそれぞれ独立して水素原子または置換基を表し、
R2~R11のうち、隣接する2つは結合して環を形成していてもよい;
ただし、R2~R11の少なくとも1つはニトロ基、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。
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