WO2023149273A1 - Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image - Google Patents
Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Download PDFInfo
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- WO2023149273A1 WO2023149273A1 PCT/JP2023/001999 JP2023001999W WO2023149273A1 WO 2023149273 A1 WO2023149273 A1 WO 2023149273A1 JP 2023001999 W JP2023001999 W JP 2023001999W WO 2023149273 A1 WO2023149273 A1 WO 2023149273A1
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- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 claims abstract description 11
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- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 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
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 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
- 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
- 239000011254 layer-forming composition Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 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
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 239000010446 mirabilite 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 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
- 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
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 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
- 230000036961 partial effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 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
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229940067265 pigment yellow 138 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
- 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
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 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
- 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
- 229940079877 pyrogallol Drugs 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 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
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 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
- 239000000725 suspension Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 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
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
Definitions
- the present invention relates to a coloring composition containing a pigment.
- 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.
- 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 Literature 1 describes forming colored pixels of a color filter using a coloring composition using a specific salen compound as a coloring agent.
- optical filters such as color filters have pixels of multiple colors.
- Such an optical filter having pixels of a plurality of colors is manufactured by sequentially forming pixels of each color.
- the coloring composition containing a pigment if the dispersibility of the pigment in the coloring composition is insufficient, the pigment aggregates in the coloring composition and becomes coarse, and the viscosity of the coloring composition tends to increase. . Further, even if the viscosity of the coloring composition immediately after production is low, the viscosity may increase over time. Therefore, it is preferable that the storage stability of the coloring composition is high.
- an object of the present invention is to provide a coloring composition that is excellent in storage stability and capable of forming a film in which thermal diffusion of pigments and the like is suppressed.
- Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, and an image display device using the colored composition.
- the present invention provides the following.
- a coloring agent containing a pigment at least one compound A selected from compound A1 represented by formula (1) and compound A2 in which the compound A1 is coordinated to a metal atom; a resin; a coloring composition comprising a solvent;
- L 1 represents a divalent linking group
- R 1 to R 10 each independently represent a hydrogen atom or a substituent
- Two adjacent groups among R 1 to R 10 may combine to form a ring
- R 5 and L 1 may combine to form a ring
- R 6 and L 1 may combine to form a ring
- X 1 and X 2 each independently represent -OH, -NHR X1 or SH
- R X1 represents a hydrogen atom or a substituent, when X 1 and X 2 are each independently —NHR X1 , X 1 and X 2 may be bonded; provided that at least one of R 1 to R 10 and L 1 contains a group represented by formula (R-1); ⁇ L R1 ⁇ (Y R1 ) n (R ⁇
- Y R1 in formula (R-1) above represents —COOH, —SO 3 H, —L Y1 —NH-L Y2 —R Y1 or —NR Y2 R Y3 , L Y1 and L Y2 each independently represent —CO— or —SO 2 —;
- R Y1 represents a substituent
- R Y2 and R Y3 each independently represent a hydrogen atom or a substituent
- R Y2 and R Y3 may combine to form a ring
- Y R1 in formula (R-1) is —NR Y2 R Y3
- L R1 in formula (R-1) is an n+1 valent linking group
- the above pigments include salen pigments, diketopyrrolopyrrole pigments, isoindoline pigments, quinophthalone pigments, azomethine pigments, azo pigments, phthalocyanine pigments, naphthalocyanine pigments, squarylium pigments, croconium pigments, pyrrolopyrrole pigments, perylene pigments, and coumarin.
- ⁇ 6> The coloring composition according to any one of ⁇ 1> to ⁇ 5>, wherein the pigment includes at least one selected from the group consisting of green pigments, yellow pigments and red pigments.
- ⁇ 8> The colored composition according to any one of ⁇ 1> to ⁇ 7>, which is used for color filters.
- ⁇ 9> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 8>.
- ⁇ 10> An optical filter having the film according to ⁇ 9>.
- ⁇ 11> A solid-state imaging device having the film according to ⁇ 9>.
- ⁇ 12> An image display device comprising the film according to ⁇ 9>.
- a coloring composition that is excellent in storage stability and capable of forming a film in which thermal diffusion of pigments and the like is suppressed. Also, a film, an optical filter, a solid-state imaging device, and an image display device using the colored composition 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.
- EUV light extreme ultraviolet rays
- (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 agent comprising a pigment; at least one compound A selected from compound A1 represented by formula (1) described later and compound A2 in which compound A1 is coordinated to a metal atom; a resin; and a solvent.
- the coloring composition of the present invention has excellent storage stability.
- a film can be formed in which thermal diffusion of pigments is suppressed.
- the compound A described above easily interacts with the pigment, and therefore, a strong network of the resin, the pigment and the compound A is formed in the coloring composition. Therefore, it is presumed that the dispersed state of the pigment in the coloring composition could be stably maintained, and as a result, a coloring composition having excellent storage stability could be obtained.
- a strong network can be formed among the resin, the pigment, and the compound A in the film, and the formation of such a network is presumed to suppress the movement of the pigment. For this reason, it is presumed that a film in which thermal diffusion of the pigment or the like was suppressed could be formed.
- the coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters, and more preferably used for color 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. Examples of the types of 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 green pixels are preferred. more preferred.
- 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 contained in the coloring composition of the present invention, one containing a pigment is used.
- the pigment may be either an inorganic pigment or an organic pigment, but an organic pigment is preferred from the viewpoints of color variation, ease of dispersibility, safety, and the like.
- the average primary particle size of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
- the primary particle diameter of the pigment can be determined from the image photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle size in this specification is the arithmetic mean value of the primary particle sizes of 400 primary particles of the pigment.
- the primary particles of the pigment refer to independent particles without agglomeration.
- 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 pigment is preferably a compound containing an aromatic ring.
- a pigment When such a pigment is used, it interacts more easily with compound A, and the storage stability of the colored composition can be further improved. Furthermore, it is also possible to form a film in which thermal diffusion of pigment or the like is more suppressed.
- Pigments include salen pigments, diketopyrrolopyrrole pigments, isoindoline pigments, quinophthalone pigments, azomethine pigments, azo pigments, phthalocyanine pigments, naphthalocyanine pigments, squarylium pigments, croconium pigments, pyrrolopyrrole pigments, perylene pigments, coumarin pigments and It is also preferable to contain at least one selected from the group consisting of pteridine pigments. These pigments interact more easily with compound A, and can further improve the storage stability of the colored composition. Furthermore, it is also possible to form a film in which thermal diffusion of pigment or the like is more suppressed.
- Pigments include yellow pigments, orange pigments, red pigments, green pigments, purple pigments, and blue pigments.
- the pigment used in the coloring composition of the present invention preferably contains at least one selected from the group consisting of a yellow pigment, a green pigment and a red pigment, and more preferably contains a yellow pigment.
- Yellow pigments include azomethine pigments, azo pigments, isoindoline pigments, pteridine pigments, quinophthalone pigments, perylene pigments, salen pigments, and diketopyrrolopyrrole pigments, and are quinophthalone pigments, isoindoline pigments or salen pigments. is preferred.
- yellow pigments 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, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187
- an azobarbiturate nickel complex having the following structure can also be used.
- the yellow pigment the quinophthalone compounds described in paragraph numbers 0011 to 0034 of JP-A-2013-054339, the quinophthalone compounds described in paragraph numbers 0013 to 0058 of JP-A-2014-026228, JP-A-2018-062644 Isoindoline compounds described in JP-A-2018-203798, quinophthalone compounds described in JP-A-2018-062578, quinophthalone compounds described in JP-A-2018-062578, quinophthalone compounds described in JP-A-6432076, JP-A-2018- Quinophthalone compounds described in JP 155881, quinophthalone compounds described in JP-A-2018-111757, quinophthalone compounds described in JP-A-2018-040835, quinophthalone compounds described in JP-A-2017-197640, JP-A A quinophthalone compound described in JP-A-2016-145282, a quinophthalone compound described in JP-A-2014-085565, a
- a quinophthalone compound described in, a quinophthalone compound described in JP-A-2019-008014, and a quinophthalone compound described in Japanese Patent No. 6607427 can also be used. Moreover, those obtained by polymerizing these compounds are also preferably used from the viewpoint of improving the color value.
- red pigments examples include diketopyrrolopyrrole pigments, anthraquinone pigments, azo pigments, naphthol pigments, azomethine pigments, xanthene pigments, quinacridone pigments, perylene pigments and thioindigo pigments, with diketopyrrolopyrrole pigments being more preferred.
- red pigments include C.I. I. 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 the like.
- red pigments diketopyrrolopyrrole compounds having at least one bromine atom substituted in the structure described in JP-A-2017-201384, diketopyrrolopyrroles described in paragraphs 0016 to 0022 of Japanese Patent No.
- 6248838 compounds diketopyrrolopyrrole compounds described in WO 2012/102399, diketopyrrolopyrrole compounds described in WO 2012/117965, brominated diketopyrrolopyrroles described in JP 2020-085947 compounds, naphthol azo compounds described in JP-A-2012-229344, red pigments described in JP-A-6516119, red pigments described in JP-A-6525101, paragraph number 0229 of JP-A-2020-090632 Brominated diketopyrrolopyrrole compound described, anthraquinone compound described in Korean Patent Publication No. 10-2019-0140741, anthraquinone compound described in Korean Patent Publication No.
- green pigments examples include phthalocyanine pigments and squarylium pigments, with phthalocyanine pigments being preferred.
- green pigments include C.I. I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66 and the like.
- a halogenated zinc phthalocyanine pigment 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.
- Specific examples include compounds described in International Publication No. 2015/118720.
- 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. is mentioned.
- C.I. I. Pigment Violet 1 19, 23, 27, 32, 37, 42, 60, 61 and the like.
- 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. be done.
- the coloring composition may contain two or more chromatic pigments.
- a coloring composition containing a yellow pigment and a green pigment can be preferably used as a coloring composition for forming green pixels of a color filter.
- a coloring composition containing a yellow pigment and a red pigment can be preferably used as a coloring composition for forming red pixels of a color filter.
- the coloring composition may contain two or more chromatic pigments, and a combination of the two or more chromatic pigments 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 pigments includes the following.
- (A1) An embodiment containing a red pigment, a blue pigment, and a yellow pigment.
- (A2) An embodiment containing a red pigment, a blue pigment, a yellow pigment, and a purple pigment.
- A3 An embodiment containing a red pigment, a blue pigment, a yellow pigment, a purple pigment, and a green pigment.
- (A5) An embodiment containing a yellow pigment and a purple pigment.
- the coloring agent contained in the coloring composition of the present invention may further contain a dye.
- the dye is not particularly limited, and known dyes can be used.
- the content of the dye is preferably 10 to 100 parts by mass with respect to 100 parts by mass of the pigment.
- the upper limit is preferably 80 parts by mass or less, more preferably 70 parts by mass or less.
- the lower limit is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and even more preferably 40 parts by mass or more. Only one dye may be used, or two or more dyes may be used in combination.
- the coloring agent contained in the coloring composition of the present invention may be substantially free of dyes. “Substantially free of dye” means that the dye content in the colorant is 0.1% by mass or less, preferably 0.01% by mass or less, and more preferably no dye. .
- a pigment multimer can also be used as a coloring agent.
- a dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures.
- the upper limit is not particularly limited, but may be 100 or less.
- a plurality of dye structures in one molecule may be the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
- the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
- the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
- Dye multimers are described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016/031442, etc. Compounds can also be used.
- Colorants include diarylmethane compounds described in JP-A-2020-504758, triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, and those described in International Publication No. 2020/174991. Phthalocyanine compounds, isoindoline compounds or salts thereof described in JP-A-2020-160279, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442, Korean Patent Publication No. 10-2020 -0069730, the compound represented by Formula 1 described in Korean Patent Publication No. 10-2020-0069070, the compound represented by Formula 1 described in Korean Patent Publication No. 10-2020-0069067. The compound represented by Formula 1, the compound represented by Formula 1 described in Korean Patent Publication No.
- the chromatic colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, may be used in the rod-like structure, or may be used in both structures.
- the content of the coloring agent in the total solid content of the coloring composition is preferably 20% by mass or more, more preferably 30% by mass or more, still more preferably 40% by mass or more, and 50% by mass. It is particularly preferable that it is above.
- 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 the pigment in the total solid content of the coloring composition is preferably 20% by mass or more, more preferably 30% by mass or more, still more preferably 40% by mass or more, 50% by mass or more is particularly preferred.
- 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 the pigment in the coloring agent contained in the coloring composition is preferably 20 to 100% by mass, more preferably 50 to 100% by mass, even more preferably 70 to 100% by mass. , 90 to 100% by weight.
- the content of the yellow pigment in the coloring agent is preferably 90% by mass or more, more preferably 95% by mass or more. More preferably, it is 99% by mass or more.
- 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 pigment and a green pigment.
- the mass ratio of the yellow pigment to the green pigment is preferably 1 to 70 parts by mass, more preferably 10 to 60 parts by mass, of the yellow pigment with respect to 100 parts by mass of the green pigment.
- the total content of the yellow pigment and the green pigment in the colorant is preferably 20 to 100% by mass, more preferably 50 to 100% by mass.
- 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 pigment containing a yellow pigment and a red pigment.
- the mass ratio of the yellow pigment to the red pigment is preferably 1 to 70 parts by mass, more preferably 10 to 60 parts by mass, per 100 parts by mass of the red pigment.
- the total content of the yellow pigment and the red pigment in the colorant is preferably 20 to 100% by mass, more preferably 50 to 100% by mass.
- the coloring composition of the present invention contains at least one compound A selected from compound A1 represented by formula (1) and compound A2 in which compound A1 is coordinated to a metal atom.
- L 1 represents a divalent linking group
- R 1 to R 10 each independently represent a hydrogen atom or a substituent
- Two adjacent groups among R 1 to R 10 may combine to form a ring
- R 5 and L 1 may combine to form a ring
- R 6 and L 1 may combine to form a ring
- X 1 and X 2 each independently represent -OH, -NHR X1 or SH
- R X1 represents a hydrogen atom or a substituent, when X 1 and X 2 are each independently —NHR X1 , X 1 and X 2 may be bonded; provided that at least one of R 1 to R 10 and L 1 contains a group represented by formula (R-1); ⁇ L R1 ⁇ (Y R1 ) n (R ⁇ 1) In formula (R-1), L R1 represents a single
- the divalent linking group represented by L 1 in formula (1) includes an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, - OCO-, -SO 2 -, -NR L1 -, -NR L1 CO-, -CONR L1 -, -NR L1 SO 2 -, -SO 2 NR L1 - and groups consisting of combinations thereof.
- RL1 represents a hydrogen atom, an alkyl group or an aryl group.
- the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. Moreover, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Moreover, the cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, even more preferably 1-10, and particularly preferably 1-5.
- the aromatic hydrocarbon group is preferably a monocyclic or condensed ring aromatic hydrocarbon group having 2 to 4 condensed rings. The aromatic hydrocarbon group is preferably a benzene ring group.
- the heterocyclic group is preferably a monocyclic ring or a condensed ring having 2 to 4 condensed rings.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1-3.
- a heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3-30, more preferably 3-18, and more preferably 3-12.
- the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described later and the groups represented by the formula (R-1).
- Substituents other than the group represented by formula (R-1) include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, nitro groups, alkoxy groups, aryloxy groups, hetero aryloxy group, acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heteroarylthio group, sulfamoyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, acyl group,
- the number of carbon atoms in the alkyl group represented by R L1 is preferably 1-20, more preferably 1-15, even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group represented by R L1 may further have a substituent. Examples of the substituent include the substituent T described later.
- the aryl group represented by R L1 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 represented by R L1 may further have a substituent. Examples of the substituent include the substituent T described later.
- the divalent linking group represented by L 1 in formula (1) is preferably an aromatic hydrocarbon group, more preferably a benzene ring group.
- R 1 to R 10 in formula (1) each independently represent a hydrogen atom or a substituent.
- Substituents include a substituent T described later and a group represented by formula (R-1).
- Substituents other than the group represented by formula (R-1) include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, nitro groups, alkoxy groups, aryloxy groups, hetero aryloxy group, acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heteroarylthio group, sulfamoyl
- R 1 to R 10 in formula (1) may combine to form a ring
- R 5 and L 1 may combine to form a ring
- R 6 and L 1 may combine to form a ring.
- the ring formed is preferably a 5- or 6-membered ring.
- the ring formed is preferably an aromatic ring, more preferably a benzene ring or a naphthalene ring, and even more preferably a benzene ring.
- the formed ring may further have a substituent.
- Substituents include a substituent T described below and a group represented by formula (R-1).
- X 1 and X 2 in formula (1) each independently represent -OH, -NHR X1 or SH, and R X1 represents a hydrogen atom or a substituent.
- R X1 represents a hydrogen atom or a substituent.
- Substituents represented by R X1 include an alkyl group and an aryl group.
- the number of carbon atoms in the alkyl group is preferably 1-20, more preferably 1-15, even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the number of carbon atoms in the aryl group is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- the alkyl group and aryl group may further have a substituent. Examples of the substituent include the substituent T described later.
- X 1 and X 2 in formula (1) are each independently —OH.
- At least one of R 1 to R 10 and L 1 contains a group represented by formula (R-1), and at least R 1 to R 4 , R 7 to R 10 and L 1 It is preferred that one contains a group represented by formula (R-1). Further, in the formula (1), it is preferable that any one of the following conditions 1 to 5 is satisfied, and it is more preferable that any one of the conditions 1 to 3 is satisfied.
- Condition 1 At least one of R 1 to R 10 (preferably at least one of R 1 to R 4 and R 7 to R 10 ) is a group represented by formula (R-1).
- Condition 2 L 1 contains a group represented by formula (R-1).
- Condition 3 Two adjacent groups among R 1 to R 10 are bonded to form a ring, and at least one of the formed rings contains a group represented by formula (R-1).
- Condition 4 R 5 and L 1 are combined to form a ring, and the formed ring contains a group represented by formula (R-1).
- Condition 5 R 6 and L 1 are combined to form a ring, and the formed ring contains a group represented by formula (R-1).
- the number of groups represented by formula (R-1) in formula (1) is preferably 1 to 4, and 1 or 2 for the reason that the storage stability of the coloring composition can be further improved. One is more preferable, and two is even more preferable.
- formula (1) contains two groups represented by formula (R-1), it preferably contains a group represented by formula (R-1) at a symmetrical position. Further, when the formula (1) has two or more groups represented by the formula (R-1), the effect of the present invention is more remarkably exhibited.
- Y R1 in the group represented by (R-1) are all preferably acid groups or basic groups.
- any one of R 1 to R 4 and any one of R 7 to R 10 in formula (1) each contain one group represented by formula (R-1). aspects. Preferred specific examples of this aspect include an aspect in which R 1 and R 10 each contain one group represented by formula (R-1), and R 2 and R 9 are each represented by formula (R-1). an embodiment containing one group, an embodiment in which R 3 and R 8 each contain one group represented by formula (R-1), or R 4 and R 7 each represented by formula (R-1) R 2 and R 9 each contain one group represented by the formula (R-1), preferably R 2 and R 9 each contain one group represented by the formula (R- A more preferred embodiment is the group represented by 1).
- L 1 of formula (1) contains a group represented by formula (R-1).
- L 1 preferably contains 1 to 4 groups represented by formula (R-1), more preferably 1 or 2 groups, and still more preferably 2 groups.
- L R1 in formula (R-1) represents a single bond or an n+1-valent linking group, preferably an n+1-valent linking group.
- the n+1-valent linking group represented by L R1 includes an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NR L10 -, -N ⁇ , -NR L10 CO-, -CONR L10 -, -NR L10 SO 2 -, -SO 2 NR L10 - and groups consisting of combinations thereof.
- RL10 represents a hydrogen atom, an alkyl group or an aryl group.
- the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. Moreover, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Moreover, the cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, even more preferably 1-10, and particularly preferably 1-5.
- the aromatic hydrocarbon group is preferably a monocyclic or condensed ring aromatic hydrocarbon group having 2 to 4 condensed rings. The aromatic hydrocarbon group is preferably a benzene ring group.
- the heterocyclic group is preferably a monocyclic ring or a condensed ring having 2 to 4 condensed rings.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1-3.
- a heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3-30, more preferably 3-18, and more preferably 3-12.
- the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent. Substituents include alkyl groups and aryl groups.
- the n+1-valent linking group represented by L R1 is a group obtained by combining —O— and an aliphatic hydrocarbon group, a group obtained by combining —NR L10 — and an aliphatic hydrocarbon group, or —N ⁇ and an aliphatic It is preferably a group in combination with a hydrocarbon group, more preferably a group in which —O— is combined with an aliphatic hydrocarbon group or a group in which —NR L10 — is combined with an aliphatic hydrocarbon group. , —O— and an aliphatic hydrocarbon group are more preferred.
- Y R1 in formula (R-1) represents an acid group or a basic group.
- Examples of the acid group represented by Y R1 include —COOH, —SO 3 H, and —L Y1 —NH-L Y2 —R Y1 . It is preferably 3 H or -L Y1 -NH-L Y2 -R Y1 .
- L Y1 and L Y2 each independently represent —CO— or —SO 2 —, and R Y1 represents a substituent.
- At least one of L Y1 and L Y2 is preferably —SO 2 —, and more preferably L Y2 is —SO 2 —.
- the substituent represented by RY1 includes an alkyl group and an aryl group. Alkyl groups and aryl groups may have substituents.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Basic groups represented by Y R1 include —NR Y2 R Y3 .
- R Y2 and R Y3 each independently represent a hydrogen atom or a substituent, preferably a hydrogen atom, an alkyl group or an aryl group, more preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, particularly preferably 1 or 2, and most preferably 1.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the number of carbon atoms in the aryl group is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- R Y2 and R Y3 may combine to form a ring, but preferably do not form a ring.
- the formed ring includes a pyrrolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, and the like.
- piperazine A ring, a piperidine ring or a pyrrolidine ring is preferred.
- the formed ring may further have a substituent. Examples of substituents include halogen atoms, alkyl groups, and aryl groups.
- n in formula (R-1) represents an integer of 1 to 4, preferably 1 or 2, more preferably 1.
- Substituent T includes the following groups.
- 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 heteroaryl group preferably a heteroaryl 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
- heteroaryloxy group preferably carbon 1 to 30 heteroaryloxy groups
- acyl groups preferably acyl groups having 2 to 30 carbon
- Compound A1 is preferably a compound represented by formula (3).
- R 31 to R 44 each independently represent a hydrogen atom or a substituent, and two adjacent groups among R 31 to R 42 may combine to form a ring
- X 3 and X 4 each independently represent -OH, -NHR X1 or SH
- R X1 represents a hydrogen atom or a substituent, when X 3 and X 4 are each independently —NHR X1 , X 3 and X 4 may be bonded;
- at least one of R 31 to R 42 contains a group represented by formula (R-1).
- X3 and X4 in formula (3) are synonymous with X1 and X4 in formula (1).
- Examples of substituents represented by R 31 to R 44 in formula (3) include the groups exemplified for the substituent T described above and the groups represented by formula (R-1).
- Substituents other than the group represented by formula (R-1) include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, nitro groups, alkoxy groups, aryloxy groups, heteroaryloxy group, acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heteroarylthio group, sulfamoyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, acyl group,
- 1 to 4 of R 31 to R 44 are preferably groups represented by formula (R-1), and 1 or 2 of them are represented by formula (R-1). groups, and more preferably two groups represented by formula (R-1).
- formula (3) contains two groups represented by formula (R-1), it preferably contains a group represented by formula (R-1) at a symmetrical position.
- Specific examples including the group represented by formula (R-1) at the symmetrical position include the following ⁇ 1> to ⁇ 6>, with ⁇ 2>, ⁇ 3> or ⁇ 4> being preferred.
- Each of R 31 and R 44 is a group represented by formula (R-1).
- Each of R 32 and R 43 is a group represented by formula (R-1).
- Each of R 33 and R 42 is a group represented by formula (R-1).
- Each of R 34 and R 41 is a group represented by formula (R-1).
- Each of R 36 and R 39 is a group represented by formula (R-1).
- Each of R 37 and R 38 is a group represented by formula (R-1).
- compound A2 is a compound having a structure in which the aforementioned compound A1 is coordinated to a metal atom.
- the metal atoms include Ti, Mn, Fe, Co, Pd, Cu, Zn, Ni and Al, preferably Pd, Cu, Zn, Ni or Al, preferably Cu, Zn or Ni. Cu or Zn is more preferred, and Cu or Zn is even more preferred.
- one compound A1 may be coordinated to these metal atoms, or two or more compounds may be coordinated. Further, the metal atom may be further coordinated with a ligand (another ligand) other than the compound A1.
- Ligands include halogen atoms (chlorine atom, bromine atom, fluorine atom, etc.), 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 (e.g., triethylamine, N,N,N',N'-tetramethylenediamine, ethylenediaminetetraacetic acid N,N,N',N'',N'- pentamethyldiethylenetriamine, etc.), amide compounds (eg, N,N-dimethylacetamide,
- Examples of the compound A2 include compounds represented by the following formula (1-1).
- M 1 represents a metal atom that may be coordinated with a ligand
- L 1 represents a divalent linking group
- R 1 to R 10 each independently represent a hydrogen atom or a substituent
- Two adjacent groups among R 1 to R 10 may combine to form a ring
- R 5 and L 1 may combine to form a ring
- R 6 and L 1 may combine to form a ring
- X 1a and X 2a each independently represent -O- , -N - R X1 or S-
- R X1 represents a hydrogen atom or a substituent, when X 1a and X 2a are each independently —N — R X1 , X 1a and X 2a may be bonded;
- at least one of R 1 to R 10 and L 1 includes a group represented by formula (R-1).
- Examples of the metal atom represented by M 1 in formula (1-1) include the metal atoms described above.
- the ligands that may be coordinated to the metal atom include the ligands described above.
- compound A examples include compounds of structural examples (A-1) to (A-85) shown in the table below.
- the compounds of structural examples (A-1) to (A-3), (A-7) to (A-49), and (A-52) to (A-84) are described in the column of metal atoms.
- the compound of (A-51) is a compound in which the metal atom described in the metal atom is coordinated with the compound having the structure described in the column of formula (1a) and the compound described in the column of other ligands.
- the compound of Structural Example (A-85) is a compound having the structure described in Formula (1a).
- Specific examples of compound A also include compounds having structures described in the column of formula (1a) in structural examples (A-1) to (A-84).
- the structure of each element constituting R 1 to R 10 and L 1 in the following formula (1a) is shown in the table below.
- the wavy line in the structural formulas in the table below represents the bonding position, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, Octyl represents an octyl group, and Ph represents a phenyl group. .
- Structural formulas represented in two columns are groups described in the table in which two groups are bonded. means that it forms For example, in Structural Example (A-33), R 3 and R 4 , and R 7 and R 8 respectively combine to form a benzene ring.
- r-1 to r-10 in the above table are groups having the structures shown below.
- the content of compound A in the total solid content of the coloring composition is preferably 0.3 to 40% 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.
- the content of compound A is preferably 0.1 to 50 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 1 part by mass or more, more preferably 5 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 35 parts 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 of the resin is preferably 3,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, more preferably 5000 or more.
- resins include (meth)acrylic resins, epoxy resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, Polyamide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, vinyl acetate resins, polyvinyl alcohol resins, polyvinyl acetal resins, polyurethane resins, polyurea resins, and the like.
- norbornene resin is preferable from the viewpoint of improving heat resistance.
- Commercially available norbornene resins include, for example, the ARTON series manufactured by JSR Corporation (for example, ARTON F4520). Further, as the resin, the resin described in the examples of International Publication No.
- a resin having a fluorene skeleton can also be preferably used.
- the description of US Patent Application Publication No. 2017/0102610 can be referred to, the content of which is incorporated herein.
- the resin the resin described in paragraphs 0199 to 0233 of JP-A-2020-186373, the alkali-soluble resin described in JP-A-2020-186325, and the Korean Patent Publication No. 10-2020-0078339.
- a resin represented by the formula 1 can also be used.
- a resin having an acid group As the resin.
- acid groups include carboxy groups, phosphoric acid groups, sulfo groups, and phenolic hydroxy groups. Only one kind of these acid groups may be used, or two or more kinds thereof may be used.
- a resin having an acid group can be used, for example, as an alkali-soluble resin.
- the acid value of the resin having acid groups is preferably 30-500 mgKOH/g.
- the lower limit is preferably 50 mgKOH/g or more, more preferably 70 mgKOH/g or more.
- the upper limit is preferably 400 mgKOH/g or less, more preferably 200 mgKOH/g or less, still more preferably 150 mgKOH/g or less, and most preferably 120 mgKOH/g or less.
- 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.
- Examples of the basic group contained in the resin having a basic group include groups represented by the following formula (a-1) and groups represented by the following formula (a-2).
- R a1 and R a2 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R a1 and R a2 may combine to form a ring;
- R a11 represents a hydrogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an acyl group or an oxy radical
- R a12 to R a19 each independently , represents a hydrogen atom, an alkyl group or an aryl group.
- the number of carbon atoms in the alkyl groups represented by R a1 , R a2 and R a11 to R a19 is preferably 1-30, more preferably 1-15, still more preferably 1-8, and particularly preferably 1-5.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent.
- the aryl group represented by R a1 , R a2 , and R a11 to R a19 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.
- the number of carbon atoms in the alkoxy group represented by R a11 is preferably 1 to 30, more preferably 1 to 15, even more preferably 1 to 8, and particularly preferably 1 to 5.
- the alkoxy group may have a substituent.
- the aryloxy group represented by R a11 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the aryloxy group may have a substituent.
- the acyl group represented by R a11 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and still more preferably 2 to 12 carbon atoms.
- the acyl group may have a substituent.
- 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 Japan), SOLSPERSE11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 375 00, 38500, 39000, 53095 , 56000, 7100 (manufactured by Nippon Lubrizol), Efka PX 4300, 4330, 4046, 4060, 4080 (manufactured by BASF).
- 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.
- block copolymers A1 can also be used, 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.
- a resin containing a repeating unit derived from a compound represented by the formula (ED1) and/or a compound represented by the formula (ED2) (hereinafter, these compounds may be referred to as an "ether dimer"). It is also preferred to include
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to.
- paragraph number 0317 of JP-A-2013-029760 can be referred to, the content of which is incorporated herein.
- the resin preferably contains a resin containing a repeating unit having a polymerizable group.
- the polymerizable group include ethylenically unsaturated bond-containing groups.
- 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.).
- 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.
- Examples of the aromatic carboxy group-containing group represented by Ar 1 in formula (Ac-1) include structures derived from aromatic tricarboxylic acid anhydrides, structures derived from aromatic tetracarboxylic acid anhydrides, and the like.
- Examples of 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 polymerizable group.
- the polymerizable 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 carboxy 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, 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, 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- is preferably a hydrocarbon group or a group of a combination of a hydrocarbon group and —O—.
- L 12c represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 in 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 an ethylenically unsaturated bond-containing group or a cyclic ether group.
- 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 resin having an aromatic carboxy group (resin Ac).
- resin Ac resin having an aromatic carboxy group
- examples of the resin having an aromatic carboxyl group include those mentioned above.
- 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.
- paragraph numbers 0022 to 0097 of JP-A-2009-203462 and paragraph numbers 0102-0166 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. More preferably, it is 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 International Publication No. 2016/104803, a block copolymer described in International Publication No. 2019/125940, a block polymer having an acrylamide structural unit described in JP-A-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 Japan, SOLSPERSE series manufactured by Lubrizol Japan, Efka series manufactured by BASF, and Ajinomoto Fine Techno ( Co., Ltd. Ajisper series and the like.
- the product described in paragraph number 0129 of JP-A-2012-137564 and the product described in paragraph number 0235 of JP-A-2017-194662 can also be used as a dispersant.
- the resin content in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the acid group-containing resin in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the dispersant is preferably 10 to 100 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more.
- the upper limit is preferably 80 parts by mass or less, more preferably 60 parts by mass or less.
- 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 contains a solvent.
- An organic solvent is mentioned as a solvent.
- the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
- Organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For these details, reference can be made to paragraph number 0223 of WO2015/166779, the content of which is incorporated herein. Ester-based solvents substituted with cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups can also be preferably used.
- 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, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol acetate, butylcarbylate tall acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-di
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (e.g., 50 mass ppm (parts per million), 10 ppm by mass or less, or 1 ppm by mass or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a mass ppt (parts per trillion) level 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.
- a method for reducing the amount of environmentally regulated substances there is a method in which the system is heated or decompressed to raise the temperature to the boiling point of the environmentally regulated substances or higher, and the environmentally regulated substances are distilled off from the system.
- distilling 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 preferably contains a polymerizable compound.
- a polymerizable compound known compounds that can be crosslinked by radicals, acids or heat can be used.
- the polymerizable compound is preferably a compound having an ethylenically unsaturated bond-containing group. Examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- 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 more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, even more preferably 250 or more.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, an ethylenically unsaturated bond Compounds containing 3 to 6 containing groups are more preferred.
- the polymerizable compound is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound.
- polymerizable compound examples include paragraph numbers 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraph numbers 0254-0257 of JP-A-2008-292970, and JP-A-2008-292970. 2013-253224, paragraphs 0034 to 0038, JP 2012-208494, paragraph 0477, JP 2017-048367, JP 6057891, the compound described in JP 6031807 , the contents of which are incorporated herein.
- dipentaerythritol tri(meth)acrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available as KAYARAD D-320 manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (as a commercial product, KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (as a commercial product, KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and their (meth)acryloyl groups via ethylene glycol and/or propylene glycol residues
- Compounds of conjugated structures (eg SR454,
- diglycerin EO ethylene oxide modified (meth) acrylate
- pentaerythritol tetraacrylate 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 manufactured by Toagosei Co., Ltd.
- NK Oligo UA-7200 manufactured by Shin-Nakamura Chemical Co., Ltd.
- DPHA-40H manufactured by Nippon Kayaku Co., Ltd.
- Polymerizable compounds include trimethylolpropane tri(meth)acrylate, trimethylolpropane propyleneoxy-modified tri(meth)acrylate, trimethylolpropane ethyleneoxy-modified tri(meth)acrylate, isocyanuric acid ethyleneoxy-modified tri(meth)acrylate, Trifunctional (meth)acrylate compounds such as pentaerythritol tri(meth)acrylate can also be used.
- 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 can also be used as the polymerizable compound.
- the acid group includes a carboxy group, a sulfo group, a phosphoric acid group and the like, and a carboxy group is preferred.
- Examples of the polymerizable compound having an acid group include succinic acid-modified dipentaerythritol penta(meth)acrylate.
- Commercially available polymerizable compounds having an acid group include Aronix M-510, M-520 and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the acid value of the polymerizable compound having an acid group is preferably 0.1-40 mgKOH/g, more preferably 5-30 mgKOH/g.
- the acid value of the polymerizable compound is 0.1 mgKOH/g or more, the solubility in the developer is good, and when it is 40 mgKOH/g or less, it is advantageous in terms of production and handling.
- a compound having a caprolactone structure can also be used as the polymerizable compound.
- Commercially available polymerizable compounds having a caprolactone structure include KAYARAD DPCA-20, DPCA-30, DPCA-60, and DPCA-120 (manufactured by Nippon Kayaku Co., Ltd.).
- a polymerizable compound having an alkyleneoxy group can also be used as the polymerizable compound.
- the polymerizable compound having an alkyleneoxy group is preferably a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a polymerizable compound having an ethyleneoxy group, and 3 to 4 having 4 to 20 ethyleneoxy groups.
- a hexafunctional (meth)acrylate compound is more preferred.
- Commercially available polymerizable compounds having an alkyleneoxy group include, for example, SR-494, a tetrafunctional (meth)acrylate having four ethyleneoxy groups manufactured by Sartomer Co., Ltd., and an isobutyleneoxy group manufactured by Nippon Kayaku Co., Ltd. KAYARAD TPA-330, which is a trifunctional (meth)acrylate having three.
- a polymerizable compound having a fluorene skeleton can also be used as the polymerizable compound.
- Commercially available polymerizable compounds having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).
- the polymerizable compound it is also preferable to use a compound that does not substantially contain environmentally regulated substances such as toluene.
- environmentally regulated substances such as toluene.
- Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- the content of the polymerizable compound in the total solid content of the coloring composition is preferably 0.1 to 50% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more, and even more preferably 3% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less.
- the coloring composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. 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 preferably 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 range to the visible range 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. is 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, BASF company) and the like.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, and Irgacure 3.
- 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-(O-acetyloxime) and the like.
- 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.
- 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 from the viewpoint of sensitivity, more preferably 1000 to 300000, further preferably 2000 to 300000, even more preferably 5000 to 200000. 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.
- the coloring composition of the present invention may contain only one type of photopolymerization initiator, or may contain two or more types. When two or more photopolymerization initiators are included, the total amount thereof preferably falls within the above range.
- the coloring composition of the present invention can contain a pigment derivative (hereinafter also referred to as another pigment derivative) other than the compound A described above.
- a pigment derivative hereinafter also referred to as another pigment derivative
- Other 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, 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 compounds described in JP-A-56-118462, compounds described in JP-A-63-264674, compounds described in JP-A-01-217077, JP-A-03- 009961, the compound described in JP-A-03-026767, the compound described in JP-A-03-153780, the compound described in JP-A-03-045662, JP-A-04-285669 Compounds described in publications, compounds described in JP-A-06-145546, compounds described in JP-A-06-212088, compounds described in JP-A-06-240158, JP-A-10-030063 Compounds described, compounds described in JP-A-10-195326, compounds described in paragraphs 0086 to 0098 of WO 2011/024896, WO 2012/102399 described in paragraphs 0063 to 0094 Compounds, compounds described in paragraph number 0082 of WO 2017/038252, compounds described in paragraph number 0171 of JP 2015-151530, J
- the content of the other pigment derivative is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, still more preferably 15 parts by mass or less, and 10 parts by mass with respect to 100 parts by mass of the pigment. Part or less is particularly preferred.
- the total content of the other pigment derivative and compound A described above is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 2 parts by mass or more, more preferably 3 parts by mass or more.
- the upper limit is preferably 30 parts by mass or less, more preferably 20 parts by mass or less.
- Other pigment derivatives may be used alone or in combination of two or more. 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 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 the light transmitted through the film obtained by containing an infrared absorbing agent in the coloring composition is shifted to the 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 700 nm or more 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.
- Examples of croconium compounds include compounds described in JP-A-2017-082029.
- As 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.
- Examples 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.
- Compounds described in Nos. 0029-0076 can be mentioned.
- Examples of 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.
- Commercially available lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.).
- the compound as described in international publication 2017/119394 can also be used.
- commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- the 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.
- tungsten oxide represented by the following formula described in paragraph 0025 of EP 3628645 can also be used.
- M 1 and M 2 represent an ammonium cation or a metal cation
- a is 0.01 to 0.5
- b is 0 to 0.5
- c is 1
- d is 2.5 to 3.
- e 0.01 to 0.75
- n is 1, 2 or 3
- m is 1, 2 or 3
- R is a hydrocarbon group optionally having a substituent show.
- 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 compound having a cyclic ether group.
- Cyclic ether groups include epoxy groups and oxetanyl groups.
- the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound).
- a compound having a cyclic ether group may be a low-molecular compound (for example, a molecular weight of less than 1000) or a macromolecule (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight-average molecular weight of 1000 or more).
- the weight average molecular weight of the cyclic ether group is preferably from 200 to 100,000, more preferably from 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
- Epoxy resin can be preferably used as the epoxy compound.
- epoxy resins include epoxy resins that are glycidyl etherified compounds of phenolic compounds, epoxy resins that are glycidyl etherified compounds of various novolak resins, alicyclic epoxy resins, aliphatic epoxy resins, heterocyclic epoxy resins, glycidyl esters, epoxy resins, glycidylamine-based epoxy resins, epoxy resins obtained by glycidylating halogenated phenols, condensation products of silicon compounds with epoxy groups and other silicon compounds, polymerizable unsaturated compounds with epoxy groups and others and copolymers with other polymerizable unsaturated compounds.
- the epoxy equivalent of the epoxy resin is preferably 310 to 3300 g/eq, more preferably 310 to 1700 g/eq, even more preferably 310 to 1000 g/eq.
- Examples of commercially available compounds having a cyclic ether group include EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), Marproof G-0150M, G-0105SA, G-0130SP, G -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (these are epoxy group-containing polymers manufactured by NOF Corporation) and the like.
- the content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 20% by mass.
- the lower limit is, for example, preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the upper limit is, for example, preferably 15% by mass or less, more preferably 10% by mass or less.
- the coloring composition of the present invention may contain only one type of compound having a cyclic ether group, or may contain two or more types. When two or more compounds having a cyclic ether group are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can 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, carboxy group-containing epoxy curing agents described in JP-A-2017-036379, and the like.
- 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, triazine compounds, and dibenzoyl 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.
- the coloring composition of the present invention may contain only one type of UV absorber, or may contain two or more types. When two or more ultraviolet absorbers are included, the total amount thereof 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.
- the coloring composition of the present invention may contain only one type of polymerization inhibitor, or may contain two or more types. When two or more polymerization inhibitors are included, the total amount thereof 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 hydrolysis reaction and 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% by mass, more preferably 0.05 to 10% by mass.
- the coloring composition of the present invention may contain only one type of silane coupling agent, or may contain two or more types. When two or more silane coupling agents are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as fluorosurfactants, 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.
- 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 an 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.
- the coloring composition of the present invention may contain only one surfactant, or may contain two or more surfactants. When two or more surfactants are included, the total amount thereof 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.
- the coloring composition of the present invention may contain only one antioxidant, or may contain two or more antioxidants. When two or more kinds of antioxidants are included, it is preferable that the total amount thereof is 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 this invention may contain a latent antioxidant as needed.
- 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.
- Compounds that can substitute for the regulated compounds include, for example, compounds excluded from the regulation due to the difference in the number of carbon atoms in the perfluoroalkyl group.
- the above contents do 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 stability of the coloring composition over time, and suppressing deterioration of components.
- the coloring composition of the present invention can be prepared by mixing the aforementioned ingredients.
- all components may be simultaneously dissolved and / or dispersed in a solvent to prepare a 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 coating) 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.
- beads with a small diameter or to increase the filling rate of the beads so as to increase the pulverization efficiency.
- the process and dispersing machine for dispersing pigments are described in ⁇ Dispersion Technology Encyclopedia, Information Organization Co., Ltd., July 15, 2005'' and ⁇ Dispersion Technology Centered on Suspension (Solid/Liquid Dispersion System) and Industrial Applications'' The actual practice of comprehensive materials, published by Management Development Center Publishing Department, October 10, 1978", the process and dispersing machine described in paragraph number 0022 of JP-A-2015-157893 can be suitably used.
- the particles may be made finer in the salt milling step. 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.
- Bead materials used for dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel and glass.
- An inorganic compound having a Mohs hardness of 2 or more can also be used for the beads.
- the composition may contain 1 to 10000 ppm of the beads.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- PTFE polytetrafluoroethylene
- PVDF polyvinylidene fluoride
- polyamide resins such as nylon (eg nylon-6, nylon-6,6), polyethylene, polyolefin resins such as polypropylene (PP) ( (including high-density, ultra-high-molecular-weight polyolefin resin).
- PP polypropylene
- polypropylene including high density polypropylene
- nylon are preferred.
- 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. .
- a fiber-like filter medium As the filter.
- fiber-like filter media include polypropylene fiber, nylon fiber, and glass fiber.
- 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 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. Further, 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.
- the filter can be appropriately selected according to the hydrophilicity/hydrophobicity of the coloring composition.
- the film of the present invention is a film obtained from the colored composition of the present invention described above.
- the film of the present invention can be used in optical filters such as color filters and infrared transmission filters.
- 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, 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 light transmission in the film thickness direction. of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light in the wavelength range of 1040 nm or more.
- 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.
- 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 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 preferable.
- 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 pulses (pulse exposure).
- pulse exposure is an exposure method in which light irradiation and pause are repeated in a cycle of short time (for example, less than millisecond level).
- the dose 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 the 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 rinsing 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, and color filters are preferred.
- a color filter preferably has the film of the present invention as its colored pixels.
- 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, 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 width of pixels included in the optical filter is preferably 0.4 to 10.0 ⁇ m.
- the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and even more preferably 0.6 ⁇ m or more.
- the upper limit is preferably 5.0 ⁇ m or less, more preferably 2.0 ⁇ m or less, even more preferably 1.0 ⁇ m or less, and even more preferably 0.8 ⁇ m or less.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- Each pixel included in the optical filter preferably has high flatness.
- the pixel surface roughness Ra is preferably 100 nm or less, more preferably 40 nm or less, and even more preferably 15 nm or less. Although the lower limit is not specified, it is preferably 0.1 nm or more, for example.
- the surface roughness of a pixel can be measured using, for example, AFM (Atomic Force Microscope) Dimension 3100 manufactured by Veeco.
- the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110°. The contact angle can be measured using, for example, a contact angle meter CV-DT-A type (manufactured by Kyowa Interface Science Co., Ltd.).
- the volume resistance value of the pixel is high.
- the volume resistance value of the pixel is preferably 10 9 ⁇ cm or more, more preferably 10 11 ⁇ cm or more.
- the upper limit is not specified, it is preferably 10 14 ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
- a protective layer may be provided on the surface of the film of the present invention.
- the 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 of forming the protective layer include a method of applying a protective layer-forming composition, a chemical vapor deposition method, and a method of adhering 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.
- Resins polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, polyol resins, polyvinylidene chloride resins, melamine resins, urethane resins, aramid resins, polyamide resins, alkyd resins, epoxy resins, modified silicone resins, fluorine Resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4 and the like, and two or more of these components may be contained.
- the protective layer in the case of a protective layer intended to block oxygen, preferably contains a polyol resin, SiO 2 and Si 2 N 4 .
- the protective layer in the case of a protective layer intended to reduce reflection, preferably contains a (meth)acrylic resin and a fluororesin.
- 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 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 (written by Akio Sasaki, Industrial Research Institute, 1990)", “Display Device (written by Junsho Ibuki, Sangyo Tosho ( Co., Ltd.), issued in 1989), etc.
- Liquid crystal display devices are described, for example, in “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Choukai Co., Ltd., 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied.
- Diethylene glycol was used as a binder.
- the kneaded material after kneading and polishing was washed with 10 L of water at 24° C. to remove the grinding agent and the binder, and was treated in a heating oven at 80° C. for 24 hours.
- G1 compound having the following structure (green pigment, naphthalocyanine compound)
- PG36 C.I. I. Pigment Green 36 (green pigment, phthalocyanine pigment)
- PG58 C.I. I. Pigment Green 58 (green pigment, phthalocyanine pigment)
- PR122 C.I. I. Pigment Red 122 (red pigment, quinacridone pigment)
- PR177 C.I. I. Pigment Red 177 (red pigment, anthraquinone pigment)
- PR224 C.I. I. Pigment Red 224 (red pigment, perylene pigment)
- PR254 C.I. I. Pigment Red 254 (red pigment, diketopyrrolopyrrole pigment) PR264: C.I. I.
- Pigment Red 264 (red pigment, diketopyrrolopyrrole pigment) PR272: C.I. I. Pigment Red 272 (red pigment, diketopyrrolopyrrole pigment)
- PY129 C.I. I. Pigment Yellow 129 (yellow pigment, azomethine pigment)
- PY138 C.I. I. Pigment Yellow 138 (yellow pigment, quinophthalone pigment)
- PY139 C.I. I. Pigment Yellow 139 (yellow pigment, isoindoline pigment)
- PY185 C.I. I. Pigment Yellow 185 (yellow pigment, isoindoline pigment)
- PY215 C.I. I.
- Pigment Yellow 215 (yellow pigment, pteridine pigment)
- Y1 compound having the following structure (yellow pigment, quinophthalone pigment)
- Y2 compound having the following structure (yellow pigment, quinophthalone pigment)
- Y3 compound having the following structure (yellow pigment, salen pigment)
- Y4 compound having the following structure (yellow pigment, salen pigment)
- Y5 compound having the following structure (yellow pigment, salen pigment)
- D1 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)
- D3 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: 17,000)
- D4 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.
- D5 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.
- D6 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.
- D7 Acrylic block copolymer (EB-1) described in paragraph number 0219 of Japanese Patent No.
- D9 DISPERBYK-142 (manufactured by BYK Chemie)
- D10 Resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 6000)
- D11 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: 7,500)
- Dispersions G1 to G85, Y1, R1 to R6, y1 Dispersions G1 to G85, Y1, R1 to R6, y1 as described above
- M1 A mixture of compounds having the following structure (mixture of left compound (hexafunctional (meth)acrylate compound) and right compound (pentafunctional (meth)acrylate compound) at a molar ratio of 7:3)
- M2 a compound having the following structure
- M3 a compound having the following structure
- M4 succinic acid-modified dipentaerythritol hexaacrylate (acid value 67 mgKOH/g)
- M5 a compound having the following structure
- M6 a compound having the following structure
- W1 A compound having the following structure (weight average molecular weight: 14,000, percentage of repeating units is mol%, fluorosurfactant)
- W2 compound with the following structure (weight average molecular weight: 3000, silicone surfactant)
- UV1 compound of the following structure
- UV2 compound of the following structure
- Antioxidant I1 a compound having the following structure
- the initial viscosity (V0) of the colored composition obtained above was measured using a viscometer (manufactured by Toki Sangyo Co., Ltd., RE-85L). Then, the colored composition was allowed to stand at 45° C. for 3 days, and the viscosity (V1) after standing was measured.
- the viscosity increase rate (%) of the colored composition after standing was calculated from the following formula, and the storage stability was evaluated according to the following evaluation criteria. It can be said that the smaller the viscosity increase rate (%), the better the storage stability.
- the viscosity of the coloring composition was measured while the temperature was adjusted to 25°C.
- Viscosity increase rate (%) [(viscosity after standing (V1) - initial viscosity (V0)) / initial viscosity (V0)] x 100 ⁇ Evaluation criteria ⁇ A: 0 ⁇ viscosity increase rate ⁇ 5% B: 5% ⁇ rate of viscosity increase ⁇ 10% C: 10% ⁇ rate of viscosity increase ⁇ 15% D: 15% ⁇ rate of increase in viscosity
- the colored compositions of Examples G1 to G109 were spin-coated on a glass substrate so that the film thickness after post-baking was 0.6 ⁇ m, dried at 100 ° C. for 120 seconds with a hot plate, and further hot at 200 ° C. Heat treatment (post-baking) was performed for 300 seconds using a plate to form a film.
- the glass substrate on which the film is formed is exposed to light in the wavelength range of 300 nm to 1000 nm using an ultraviolet-visible-near-infrared spectrophotometer U-4100 (manufactured by Hitachi High-Tech Co., Ltd.) (ref. (reference); glass substrate). was measured.
- T (Tmin/Tmax) x 100 (%)
- Tmax maximum transmittance at a wavelength of 500 nm to 600 nm
- Tmin minimum transmittance at a wavelength of 620 nm to 730 nm
- evaluation criteria A: T ⁇ 10 B: 10 ⁇ T ⁇ 20 C: 20 ⁇ T ⁇ 30 D: 30 ⁇ T
- each coloring composition was applied by spin coating so that the film thickness after post-baking was 0.5 ⁇ m, and then a hot plate was applied. and heated at 100° C. for 2 minutes to obtain a colored composition layer.
- the colored composition layer was exposed to an i-line stepper exposure device (FPA-3000i5+, manufactured by Canon Inc.) at an exposure dose of 1000 mJ/cm 2 through a 5.0 ⁇ m square dot pattern mask. exposed.
- the glass wafer on which the colored composition layer after exposure is formed is placed on a horizontal rotating table of a spin shower developing machine (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developing solution (CD- 2000 (manufactured by FUJIFILM Electronic Materials Co., Ltd., 60% diluted solution) was used for puddle development at 23° C. for 60 seconds.
- a spin shower developing machine DW-30 type, manufactured by Chemitronics Co., Ltd.
- a developing solution CD- 2000 (manufactured by FUJIFILM Electronic Materials Co., Ltd., 60% diluted solution) was used for puddle development at 23° C. for 60 seconds.
- the glass wafer was fixed on a horizontal rotating table by a vacuum chuck method, and while rotating the glass wafer at a rotation speed of 50 rpm by a rotating device, deionized water was supplied in a shower form from an ejection nozzle from above the center of rotation for rinsing. and spray dried
- a heat treatment (post-baking) was performed for 300 seconds using a hot plate at 200° C. to form pixels 1 .
- a coloring composition for heat diffusion resistance evaluation is used, and the pixels 2 are formed in the same manner as the pixels 1 in the missing portions of the pixels 1 on the glass wafer. bottom.
- the transmittance (spectroscopy 1) in the wavelength range of 400 nm to 700 nm was measured using a microscope system (LVmicro V, manufactured by Lambda Vision Co., Ltd.). Thereafter, the glass wafer on which pixels 1 and 2 are formed is heated at 260° C.
- pixel 2 is examined using a microscopic system (LVmicro V, manufactured by Lambda Vision Co., Ltd.). was used to measure the transmittance (spectroscopy 2) in the wavelength range of 400 nm to 700 nm.
- spectroscopy 1 and spectroscopy 2 of pixel 2 the maximum value of the amount of change in transmittance was obtained, and the thermal diffusion resistance was evaluated according to the following criteria.
- the transmittance measurement was performed 5 times for each sample, and the average value of the results of 3 times excluding the maximum and minimum values was adopted.
- the maximum value of the amount of change in transmittance means the amount of change at the wavelength in which the amount of change in transmittance of the pixel 2 before and after heating is the largest in the wavelength range of 400 to 700 nm.
- the blue coloring composition 1 shown below was used for the coloring composition for heat-resistant diffusivity evaluation.
- Blue colored composition 1 C. I. Pigment Blue 15:6 with 118.5 parts by weight of C.I. I. Pigment Violet 23 (29.6 parts by mass), Dispersant D12 (51.9 parts by mass) and Solvent S1 (800 parts by mass) were mixed to obtain a mixture.
- the resulting mixture was subjected to dispersion treatment using Ultra Apex Mill (trade name) manufactured by Kotobuki Kogyo Co., Ltd. as a circulating dispersing device (bead mill) to obtain Dispersion B1.
- the solid content of the obtained dispersion B1 was 20.0% by mass.
- Dispersant D12 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: 20,000)
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Abstract
Sont divulgués une composition colorante, un film, un filtre optique, un élément d'imagerie à semi-conducteurs et un dispositif d'affichage d'image, la composition colorante comprenant : un agent colorant comprenant un pigment ; au moins un type d'un composé A choisi parmi un composé A1 représenté par la formule (1) et un composé A2 dans lequel le composé A1 est coordonné à un atome métallique ; une résine ; et un solvant.
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PCT/JP2023/001999 WO2023149273A1 (fr) | 2022-02-04 | 2023-01-24 | Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image |
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JP (1) | JPWO2023149273A1 (fr) |
TW (1) | TW202336118A (fr) |
WO (1) | WO2023149273A1 (fr) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63202669A (ja) * | 1987-02-12 | 1988-08-22 | チバーガイギ アクチエンゲゼルシヤフト | 金属錯塩顔料を基剤とした新規組成物ならびに新規化合物 |
JP2001040247A (ja) * | 1999-07-30 | 2001-02-13 | Kansai Paint Co Ltd | 硬化性塗料組成物及び塗膜形成法 |
WO2014157720A1 (fr) * | 2013-03-29 | 2014-10-02 | 富士フイルム株式会社 | Composition durcissable, film durci, filtre couleur, film protecteur, dispositif d'affichage et élément d'imagerie solide |
KR20200069067A (ko) * | 2018-12-06 | 2020-06-16 | 주식회사 엘지화학 | 색재 조성물, 감광성 수지 조성물, 감광재, 컬러필터, 및 디스플레이 장치 |
KR20200069056A (ko) * | 2018-12-06 | 2020-06-16 | 주식회사 엘지화학 | 색재 조성물, 감광성 수지 조성물, 감광재, 컬러필터, 및 디스플레이 장치 |
-
2023
- 2023-01-24 JP JP2023578488A patent/JPWO2023149273A1/ja active Pending
- 2023-01-24 WO PCT/JP2023/001999 patent/WO2023149273A1/fr unknown
- 2023-02-01 TW TW112103509A patent/TW202336118A/zh unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63202669A (ja) * | 1987-02-12 | 1988-08-22 | チバーガイギ アクチエンゲゼルシヤフト | 金属錯塩顔料を基剤とした新規組成物ならびに新規化合物 |
JP2001040247A (ja) * | 1999-07-30 | 2001-02-13 | Kansai Paint Co Ltd | 硬化性塗料組成物及び塗膜形成法 |
WO2014157720A1 (fr) * | 2013-03-29 | 2014-10-02 | 富士フイルム株式会社 | Composition durcissable, film durci, filtre couleur, film protecteur, dispositif d'affichage et élément d'imagerie solide |
KR20200069067A (ko) * | 2018-12-06 | 2020-06-16 | 주식회사 엘지화학 | 색재 조성물, 감광성 수지 조성물, 감광재, 컬러필터, 및 디스플레이 장치 |
KR20200069056A (ko) * | 2018-12-06 | 2020-06-16 | 주식회사 엘지화학 | 색재 조성물, 감광성 수지 조성물, 감광재, 컬러필터, 및 디스플레이 장치 |
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JPWO2023149273A1 (fr) | 2023-08-10 |
TW202336118A (zh) | 2023-09-16 |
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