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WO2023243353A1 - Composition de résine colorée, filtre optique et élément d'imagerie à semi-conducteurs - Google Patents

Composition de résine colorée, filtre optique et élément d'imagerie à semi-conducteurs Download PDF

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Publication number
WO2023243353A1
WO2023243353A1 PCT/JP2023/019511 JP2023019511W WO2023243353A1 WO 2023243353 A1 WO2023243353 A1 WO 2023243353A1 JP 2023019511 W JP2023019511 W JP 2023019511W WO 2023243353 A1 WO2023243353 A1 WO 2023243353A1
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WO
WIPO (PCT)
Prior art keywords
group
resin composition
carbon atoms
meth
colored resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2023/019511
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English (en)
Japanese (ja)
Inventor
裕史 濱木
拓磨 青木
勝治 井上
哲郎 赤坂
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to CN202380045765.4A priority Critical patent/CN119343616A/zh
Priority to KR1020247039438A priority patent/KR20250024914A/ko
Publication of WO2023243353A1 publication Critical patent/WO2023243353A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/18—Obtaining compounds having oxygen atoms directly bound to the phthalocyanine skeleton
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/20—Obtaining compounds having sulfur atoms directly bound to the phthalocyanine skeleton
    • 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
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/10—Integrated devices
    • H10F39/12—Image sensors
    • H10F39/18—Complementary metal-oxide-semiconductor [CMOS] image sensors; Photodiode array image sensors
    • H10F39/182—Colour image sensors

Definitions

  • the present invention relates to a colored resin composition, an optical filter, and a solid-state image sensor.
  • Devices such as near-infrared sensors and near-infrared cameras are used to detect people in various fields such as automobiles, home appliances, and security.
  • Such devices are equipped with a solid-state imaging device that includes an optical filter that has low transmittance for visible light and high transmittance for near-infrared rays.
  • Optical filters used in solid-state imaging devices are manufactured from colored resin compositions, for example.
  • a colored resin composition for example, a colored resin composition containing a colorant, a resin, and a solvent is known (Patent Document 1).
  • optical filters used in solid-state imaging devices are required to have sufficient heat resistance and light resistance from the viewpoint of the usage environment.
  • conventional optical filters do not necessarily have sufficient heat resistance and light resistance, and there is room for improvement.
  • the main object of the present invention is to provide a colored resin composition that can form an optical filter with excellent heat resistance.
  • the present invention provides the colored resin compositions described in [1] to [4], the optical filter described in [5], and the solid-state imaging device described in [6].
  • a colored resin composition containing a colorant, an alkali-soluble resin, and a solvent contains at least one selected from the group consisting of compounds represented by formula (I) and formula (II), A colored resin composition having a maximum absorption wavelength of 799 nm or less in the wavelength range of 380 to 1400 nm.
  • M 1 represents a divalent metal atom.
  • R 1 to R 8 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an OR 17 group.
  • a 1 to A 8 each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.
  • R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, and when two or more R 17s are present, they may be the same or different from each other.
  • M 2 represents a divalent metal atom.
  • R 9 to R 16 each independently represent a saturated hydrocarbon group having 1 to 10 carbon atoms.
  • a 9 to A 16 each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.
  • a colored resin composition that can form an optical filter with excellent heat resistance is provided. Moreover, the obtained optical filter is also excellent in terms of light resistance. Further, according to the present invention, an optical filter formed from such a colored resin composition and a solid-state imaging device including the optical filter are provided.
  • a numerical range indicated using "-" indicates a range that includes the numerical values written before and after "-" as the minimum and maximum values, respectively.
  • the upper limit value or lower limit value described in one numerical range may be replaced with the upper limit value or lower limit value of another numerical range described step by step. good.
  • the upper limit or lower limit of the numerical range may be replaced with the value shown in the Examples.
  • (meth)acrylate means acrylate or a methacrylate corresponding thereto.
  • the materials exemplified below may be used alone or in combination of two or more within the range applicable to the conditions.
  • the content of each component means the total amount of the multiple substances, unless otherwise specified.
  • the colored resin composition of the present embodiment includes a colorant (hereinafter sometimes referred to as “colorant (A)”), an alkali-soluble resin (hereinafter sometimes referred to as “resin (B)”), and a solvent (hereinafter sometimes referred to as “resin (B)”). (hereinafter sometimes referred to as “solvent (E)”).
  • the colored resin composition of the present embodiment includes a polymerizable compound (hereinafter sometimes referred to as “polymerizable compound (C)”) and a polymerization initiator (hereinafter sometimes referred to as “polymerization initiator (D)”). ), and preferably contains both a polymerizable compound and a polymerization initiator.
  • the colored resin composition of this embodiment may contain a leveling agent (hereinafter sometimes referred to as "leveling agent (F)").
  • the colorant (A) contains at least one selected from the group consisting of compounds represented by formula (I) and formula (II) (hereinafter sometimes referred to as "colorant (A1)").
  • M 1 represents a divalent metal atom.
  • divalent metal atoms include atoms such as copper, zinc, iron, cobalt, nickel, ruthenium, lead, rhodium, palladium, platinum, manganese, and tin.
  • the divalent metal atom is preferably an iron atom, a nickel atom, a palladium atom, a platinum atom, a copper atom, or a zinc atom, more preferably a nickel atom, a palladium atom, or a copper atom; It is more preferably an atom or a palladium atom, and particularly preferably a nickel atom.
  • R 1 to R 8 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an OR 17 group. In one embodiment, R 1 to R 8 may be hydrogen atoms.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms in R 1 to R 8 include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, hexyl group, octyl group, and dodecyl group; phenyl group, o- Aryl groups such as tolyl group, m-tolyl group, p-tolyl group, 2,4,6-trimethylphenyl group, and naphthyl group; aralkyl groups such as benzyl group and phenethyl group; and the like.
  • Some of the hydrogen atoms of these alkyl groups, aryl groups, and aralkyl groups may be substituted with halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.).
  • halogen atoms fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.
  • R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, and when two or more R 17s are present, they may be the same or different from each other.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms in R 17 include the groups exemplified by the hydrocarbon groups having 1 to 20 carbon atoms in R 1 to R 8 .
  • a 1 to A 8 each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms. Some of the hydrogen atoms of the aryl group and heteroaryl group may be substituted with a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.) or an alkoxy group having 1 to 20 carbon atoms. In one embodiment, A 1 to A 8 may be a phenyl group optionally substituted with an alkoxy group having 1 to 20 carbon atoms.
  • the aryl group having 6 to 20 carbon atoms in A 1 to A 8 may be, for example, a monocyclic or polycyclic (eg, bicyclic or tricyclic) aryl group.
  • Specific examples of the aryl group include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group.
  • the heteroaryl group having 3 to 20 carbon atoms in A 1 to A 8 may be, for example, a monocyclic or polycyclic (eg, bicyclic or tricyclic) heteroaryl group.
  • Specific examples of heteroaryl groups include furanyl group, benzofuranyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, benzothienyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, and indolyl group.
  • the heteroaryl group preferably has 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and still more preferably 3 to 9 carbon atoms. Further, the number of atoms constituting the ring of the heteroaryl group is preferably 5 to 10.
  • alkoxy group that may be substituted with some of the hydrogen atoms of the aryl group and heteroaryl group in A 1 to A 8 include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, and isobutoxy group.
  • the alkoxy group preferably has 1 to 18 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 8 carbon atoms.
  • M 2 represents a divalent metal atom.
  • divalent metal atoms include atoms such as copper, zinc, iron, cobalt, nickel, ruthenium, lead, rhodium, palladium, platinum, manganese, and tin.
  • the divalent metal atom is preferably an iron atom, a nickel atom, a palladium atom, a platinum atom, a copper atom, or a zinc atom, more preferably a nickel atom, a palladium atom, or a copper atom; It is more preferably an atom or a palladium atom, and particularly preferably a nickel atom.
  • R 9 to R 16 each independently represent a saturated hydrocarbon group having 1 to 10 carbon atoms.
  • the saturated hydrocarbon group having 1 to 10 carbon atoms may be linear, branched or cyclic.
  • Examples of the saturated hydrocarbon group having 1 to 10 carbon atoms include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, and decyl group.
  • Branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl; cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
  • Some of the hydrogen atoms of these saturated hydrocarbon groups may be substituted with halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.).
  • the linear alkyl group and the branched alkyl group preferably have 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms.
  • the cyclic alkyl group preferably has 3 to 10 carbon atoms, more preferably 6 to 10 carbon atoms.
  • a 9 to A 16 each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms. Some of the hydrogen atoms of the aryl group and heteroaryl group may be substituted with a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.) or an alkoxy group having 1 to 20 carbon atoms. In one embodiment, A 9 to A 16 may be a phenyl group optionally substituted with an alkoxy group having 1 to 20 carbon atoms.
  • Examples of the aryl group having 6 to 20 carbon atoms in A 9 to A 16 include groups exemplified by the aryl group having 6 to 20 carbon atoms in A 1 to A 8 .
  • Examples of the heteroaryl group having 3 to 20 carbon atoms in A 9 to A 16 include the groups exemplified by the heteroaryl group having 3 to 20 carbon atoms in A 1 to A 8 .
  • alkoxy group which may be substituted with some of the hydrogen atoms of the aryl group and heteroaryl group in A 9 to A 16 include those which are substituted with some of the hydrogen atoms of the aryl group and heteroaryl group in A 1 to A 8 .
  • Examples include groups exemplified by alkoxy groups which may be optional.
  • Colorant (A) contains, as colorant (A1), at least one compound selected from the group consisting of compounds represented by formula (I) and formula (II), preferably compounds represented by formula (I). (at least one type selected from the compounds represented by formula (I)) and the compound represented by formula (II) (at least one type selected from the compounds represented by formula (II)) . Since the colorant (A) contains both the compound represented by the formula (I) and the compound represented by the formula (II) as the colorant (A1), the sensitivity as a sensor is also good, and An optical filter having near-infrared transmittance and excellent heat resistance and light resistance can be obtained.
  • the content ratio (mass ratio) is the same as the formula ( Compound represented by I): In the compound represented by formula (II), preferably 1:10 to 10:1, more preferably 1:5 to 5:1, even more preferably 1:4 to 4:1 It is.
  • the content of the colorant (A1) is preferably 10 to 100% by mass, more preferably 20 to 100% by mass, and even more preferably 30 to 100% by mass, based on the total amount of colorant (A). In one embodiment, the content of the colorant (A1) may be 100% by mass based on the total amount of the colorant (A).
  • the colorant (A) may further contain a colorant different from the colorant (A1) (hereinafter sometimes referred to as “colorant (A2)").
  • Examples of the colorant (A2) include dyes and pigments.
  • dyes examples include compounds that are classified as having a hue other than pigments in the Color Index (published by The Society of Dyers and Colorists), and known dyes listed in Dyeing Notes (Shirosensha). .
  • a xanthene dye is a dye containing a compound having a xanthene skeleton in its molecule.
  • xanthene dyes include C.I. I. Acid Red 51 (Hereinafter, the description of "C.I. Acid Red” will be omitted and only the number will be written. Other similar expressions may also be written with only the number.), 52, 87 , 92, 94, 289, 388; C. I. Acid Violet 9, 30, 102; C. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11; C.I. I. Basic Violet 10 (Rhodamine B), 11; C.I. I. Solvent Red 218;C. I. Modern Tread 27;C. I.
  • Reactive Red 36 (Rose Bengal B); Sulforhodamine G; xanthene dye described in JP-A-2010-32999; xanthene dye described in Patent No. 4492760, and the like.
  • the xanthene dye is preferably one that is soluble in an organic solvent.
  • the xanthene dye As the xanthene dye, commercially available xanthene dyes (for example, "Chugai Aminol Fast Pink RH/C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.) can also be used. can. Further, the xanthene dye can also be synthesized using a commercially available xanthene dye as a starting material with reference to JP-A-2010-32999.
  • commercially available xanthene dyes for example, "Chugai Aminol Fast Pink RH/C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.
  • the xanthene dye can also be synthesized using a commercially available xanthene dye as a starting material with reference to JP-A-2010-32999.
  • Dyes other than xanthene dyes include azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, and acridine dyes. , styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, etc. may also be used. As dyes other than xanthene dyes, known dyes can be used.
  • dyes other than xanthene dyes include C.I. I. Solvent Yellow 4 (Hereinafter, the description of C.I. Solvent Yellow will be omitted and only the number will be written. Other similar expressions may also be written with only the number.), 14, 15, 23 , 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; C. I. Solvent red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247; C. I.
  • I. acid dye C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; C. I.
  • I. direct dye C. I. Disperse Yellow 51, 54, 76; C. I. Disperse Violet 26, 27; C. I. C.I. such as Disperse Blue 1, 14, 56, 60, etc.
  • I. disperse dye C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C. I. Basic Violet 2; C. I. Basic Red 9; C. I.
  • I. reactive dye C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C. I. Modern tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39 , 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; C. I.
  • pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). Examples of such pigments include the following pigments.
  • Green pigment C. I. Pigment Green 7, 36, 58, etc.
  • Yellow pigment C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.
  • Orange pigment C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.
  • Red pigment C.I. I.
  • pigments one type of pigment or a plurality of pigments may be used for each color, or pigments of each color may be used in combination.
  • the colorant (A2) is preferably one or more types of pigment, more preferably two or more types of pigment, and two types selected from the group consisting of an orange pigment, a purple pigment, a blue pigment, and a black pigment.
  • the above pigments are more preferable, and a combination of an orange pigment, a purple pigment and a blue pigment, or a combination of a blue pigment and a black pigment is particularly preferable.
  • Pigments are treated, as necessary, with rosin treatment; surface treatment using pigment derivatives into which acidic or basic groups have been introduced; grafting treatment on the pigment surface with polymeric compounds, etc.; atomization by sulfuric acid atomization method, etc. Treatment: Washing treatment with an organic solvent, water, etc. to remove impurities; Treatment for removing ionic impurities by an ion exchange method, etc. may be performed. It is preferable that the particle size of the pigment is substantially uniform.
  • the pigment can be made into a pigment dispersion liquid in which it is uniformly dispersed in the pigment dispersant solution.
  • Each of the pigments may be dispersed individually, or a plurality of pigments may be mixed and dispersed.
  • pigment dispersants include silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, polyester-based, polyamine-based, and acrylic-based surfactants.
  • surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethylene imines, etc. .
  • surfactants include, for example, the trade names KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by Kyoeisha Chemical Co., Ltd.), Solpers (manufactured by Zeneca Co., Ltd.), and EFKA (manufactured by BASF Japan Co., Ltd.). ), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (manufactured by Byk Chemie Co., Ltd.), and the like.
  • the amount used is preferably 10 to 200 parts by weight, more preferably 15 to 180 parts by weight, and still more preferably 20 to 160 parts by weight, based on 100 parts by weight of the pigment.
  • the amount of the pigment dispersant used is within the above range, a pigment dispersion liquid in a more uniformly dispersed state tends to be obtained when two or more types of pigments are used.
  • the content of the colorant (A2) is preferably 0 to 90% by mass, more preferably 0 to 80% by mass, and even more preferably 0 to 70% by mass, based on the total amount of colorant (A).
  • the content of the colorant (A) is preferably 1 to 60% by mass, more preferably 5 to 60% by mass, and even more preferably 10 to 60% by mass, based on the total solid content of the colored resin composition. .
  • the “total amount of solid content of the colored resin composition” means the total amount of components excluding the solvent from the colored resin composition.
  • the total solid content of the colored resin composition and the content of each component relative to the total solid content can be measured by, for example, known analytical means such as liquid chromatography and gas chromatography.
  • Resin [K1] a structural unit derived from at least one type (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides; A copolymer/resin having a cyclic ether structure having 2 to 4 carbon atoms and a structural unit derived from a monomer (b) having an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)”)
  • K2] A structural unit derived from (a), a structural unit derived from (b), and a monomer (c) copolymerizable with (a) (however, (a) and (b) are Copolymer/resin [K3] having a structural unit derived from (a) (hereinafter sometimes referred to as "(c)”): a
  • unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-Carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethy
  • (a) is preferably acrylic acid, methacrylic acid, or maleic anhydride in terms of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution.
  • (b) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one member selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
  • (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
  • (b) for example, a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)”), a monomer having an oxetanyl group and an ethylenically unsaturated bond, monomer (b2) (hereinafter sometimes referred to as “(b2)”), a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter referred to as "(b3)”) ), etc.
  • a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b1)
  • a monomer having an oxetanyl group and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b2)
  • (b3) monomer (b3) having a tetrahydrofuryl group and an
  • (b1) is, for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as "(b1-1)"). ), and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").
  • (b1-1) includes glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, ⁇ -ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, -Vinylbenzylglycidyl ether, ⁇ -methyl-o-vinylbenzylglycidyl ether, ⁇ -methyl-m-vinylbenzylglycidyl ether, ⁇ -methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyloxymethyl)styrene , 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,
  • Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g. Celoxide 2000 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g.
  • Cyclomer A400 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100 (manufactured by Daicel Corporation)), 3,4-epoxytricyclo[5.2 .1.0 2,6 ]decyl (meth)acrylate (3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate, 3,4-epoxytricyclo [5.2.1.0 2,6 ]decane-9-yl (meth)acrylate, etc.), 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyloxyethyl (meth)acrylate etc.
  • (b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group.
  • (b2) 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.
  • (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group.
  • examples of (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V #150 (manufactured by Osaka Organic Chemical Industry Co., Ltd.)), tetrahydrofurfuryl methacrylate, and the like.
  • (b) is preferably (b1) in that it can further increase the reliability of the resulting optical filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b) is more preferably (b1-2) in that the colored resin composition has excellent storage stability.
  • Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate.
  • tricyclodecyl (meth)acrylate tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate (commonly referred to as “dicyclopentenyl (meth)acrylate” in the technical field).
  • dicyclopentanyloxyethyl (meth)acrylate isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylic acid esters such as (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxy
  • (c) is selected from styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, or bicyclo[2.2.1]hept- 2-ene is preferred.
  • the ratio of structural units derived from each is as follows among all structural units constituting resin [K1]: Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (b); 40 to 98 mol% It is preferable that Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (b); 50 to 90 mol% It is more preferable that
  • the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting optical filter tend to be excellent. be.
  • the resin [K1] can be prepared, for example, by the method described in the document "Experimental Methods of Polymer Synthesis” (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972). It can be manufactured by referring to the cited documents described in this document.
  • a polymerization initiator for example, predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and a deoxidized atmosphere is created by replacing oxygen with nitrogen, for example, and while stirring, Examples include methods of heating and keeping warm.
  • the polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the field can be used.
  • a polymerization initiator an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.), an organic peroxide (benzoyl peroxide, etc.) can be mentioned.
  • the solvent may be any solvent as long as it can dissolve each monomer, and for example, those exemplified as solvent (E) below can be used.
  • the obtained copolymer may be used as it is as a solution after the reaction, or may be used as a concentrated or diluted solution. Moreover, the obtained copolymer may be used as a solid (powder) taken out by a method such as reprecipitation.
  • the solution after the reaction can be used for preparing the colored resin composition. The manufacturing process can be simplified.
  • the ratio of structural units derived from each is as follows among all structural units constituting resin [K2]: Structural unit derived from (a); 2 to 45 mol% Structural unit derived from (b); 2 to 95 mol% Structural unit derived from (c); 1 to 65 mol% It is preferable that Structural unit derived from (a); 5 to 40 mol% Structural unit derived from (b); 5 to 80 mol% Structural unit derived from (c); 5 to 60 mol% It is more preferable that
  • the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and Tends to have excellent mechanical strength.
  • Resin [K2] can be produced, for example, in the same manner as the method described as the method for producing resin [K1].
  • the ratio of structural units derived from each is as follows among all structural units constituting resin [K3]: Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (c); 40 to 98 mol% It is preferable that Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (c); 50 to 90 mol% It is more preferable that
  • Resin [K3] can be produced, for example, in the same manner as described as the method for producing resin [K1].
  • Resin [K4] is obtained by obtaining a copolymer of (a) and (c), and a carboxylic acid and/or carboxylic acid anhydride in which (a) has a cyclic ether having 2 to 4 carbon atoms in (b). It can be manufactured by adding it to.
  • a copolymer of (a) and (c) is produced in the same manner as described as the method for producing resin [K1].
  • the ratio of structural units derived from each is preferably the same as the ratio exemplified for resin [K3].
  • the amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By keeping it within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the resulting pattern tend to have a good balance among solvent resistance, heat resistance, mechanical strength, and sensitivity. be. Since the reactivity of the cyclic ether is high and unreacted (b) is difficult to remain, (b) used in the resin [K4] is preferably (b1), and (b1-1) is preferable. More preferred.
  • the amount of the above reaction catalyst used is preferably 0.001 to 5 parts by weight based on 100 parts by weight of the total amount of (a), (b) and (c).
  • the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by weight based on 100 parts by weight of the total amount of (a), (b) and (c).
  • reaction conditions such as the charging method, reaction temperature, and time can be adjusted as appropriate by taking into account the manufacturing equipment, the amount of heat generated by polymerization, and the like.
  • resin [K5] is obtained as a copolymer of (b) and (c) in the same manner as the manufacturing method of resin [K1] described above.
  • the obtained copolymer may be used as a solution after the reaction, or a concentrated or diluted solution may be used.
  • the obtained copolymer may be used as a solid (powder) taken out by a method such as reprecipitation.
  • the ratio of the structural units derived from (b) and (c) is, respectively, relative to the total number of moles of all structural units constituting the above copolymer.
  • Resin [K5] can be obtained by reacting the substances.
  • the amount of (a) used to react with the above copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the reactivity of the cyclic ether is high and it is difficult for unreacted (b) to remain, (b) used in the resin [K5] is preferably (b1), and (b1-1) is preferable. More preferred.
  • Resin [K6] is a resin obtained by reacting resin [K5] with a carboxylic acid anhydride. A carboxylic acid anhydride is reacted with a hydroxy group generated by the reaction of a cyclic ether and a carboxylic acid or a carboxylic acid anhydride.
  • carboxylic anhydrides examples include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like.
  • the amount of carboxylic acid anhydride used is preferably 0.5 to 1 mol per 1 mol of (a).
  • the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resin [K1] such as decyl acrylate/(meth)acrylic acid copolymer; glycidyl(meth)acrylate/benzyl(meth)acrylate/(meth)acrylic acid copolymer, glycidyl(meth)acrylate/styrene/(meth) Acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/benzyl(meth)acrylate, 3,4-epoxytricyclo[5.
  • Resin [K1] such as decyl acrylate/(meth)acrylic acid copolymer; glycidyl(meth)acrylate/benzyl(meth)acrylate
  • the resin (B) has a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, a cyclic ether structure having 2 to 4 carbon atoms, and an ethylenically unsaturated bond.
  • the copolymer is preferably a copolymer containing at least a structural unit having the above structure, more preferably a resin [K1] or a resin [K2], and even more preferably a resin [K2].
  • the weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, even more preferably 5,000 to 30,000.
  • the weight average molecular weight is within the above range, the hardness of the optical filter is improved, the residual film rate is high, the solubility of the unexposed area in the developer is good, and the resolution of the colored pattern tends to be improved.
  • the dispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.
  • the acid value of the resin (B) is preferably 50 to 170 mg-KOH/g, more preferably 60 to 150 mg-KOH/g, and even more preferably 70 to 135 mg-KOH/g in terms of solid content.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution. Can be done.
  • the content of the resin (B) is preferably 5 to 60% by mass, more preferably 10 to 55% by mass, and even more preferably 20 to 50% by mass, based on the total solid content of the colored resin composition.
  • the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to improve.
  • the polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D).
  • Examples of the polymerizable compound (C) include compounds having a polymerizable ethylenically unsaturated bond.
  • the polymerizable compound (C) is preferably a (meth)acrylic acid ester compound.
  • the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
  • examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa( meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl ) isocyanurate, ethylene glycol-modified pent
  • the polymerizable compound (C) is preferably trimethylolpropane triacrylate, dipentaerythritol penta(meth)acrylate, or dipentaerythritol hexa(meth)acrylate.
  • the molecular weight or weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2900, more preferably 250 to 1500.
  • the content of the polymerizable compound (C) is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and even more preferably 20 to 40% by mass, based on the total solid content of the colored resin composition. be.
  • the content of the polymerizable compound (C) is within the above range, the residual film rate during colored pattern formation and the chemical resistance of the optical filter tend to improve.
  • the polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids, etc. by the action of light or heat, and any known polymerization initiator can be used.
  • Examples of the polymerization initiator that generates active radicals include O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.
  • the O-acyloxime compound is a compound having a partial structure represented by formula (d1).
  • * represents a bond.
  • O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-( 2-Methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-(3,3-dimethyl-2,4 -dioxacyclopentanylmethyloxy)benzoyl ⁇ -9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methyl
  • O-acyl oxime compounds Irgacure (registered trademark, hereinafter the same) OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine), Irgacure OXE02 (N-acetoxy- 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine) (manufactured by BASF), N-1919 (manufactured by ADEKA Corporation), etc. Commercially available products may also be used.
  • O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenyl sulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6- Consisting of (2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine At least one member selected from the group is preferably N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-
  • the alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3).
  • the benzene ring may have a substituent.
  • Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4 -morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one etc.
  • commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may be used.
  • Examples of the compound having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2 -hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ -diethoxy Examples include acetophenone and benzyl dimethyl ketal.
  • the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).
  • triazine compounds examples include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl) naphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl) )-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4- Bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2) -methylphen
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • acylphosphine oxide compound commercially available products such as Irgacure 819 (manufactured by BASF) may be used.
  • biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4 , 4',5,5'-tetraphenylbiimidazole (for example, see JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4 ',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, -chlorophenyl)-4,4',5,5'-tetra(dialkoxyphen
  • biimidazole in which the phenyl group at the 4,4'5,5'-position is substituted with a carbalkoxy group compounds (see, for example, JP-A-7-10913), and the like.
  • benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiation aid (D1) (especially amine
  • acid-generating polymerization initiators include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxy Onium salts such as phenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylate , benzointosylates, and the like.
  • the polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds; - A polymerization initiator containing an acyloxime compound is more preferred.
  • the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is.
  • the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that it can be expected to improve the productivity of the optical filter.
  • the polymerization initiation aid (D1) is a compound or sensitizer used to promote polymerization of a polymerizable compound.
  • the colored resin composition contains a polymerization initiation aid (D1), it is usually used in combination with a polymerization initiator (D).
  • Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
  • amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and 4-dimethylaminobenzoate.
  • the amine compound commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used. Among these, the amine compound is preferably 4,4'-bis(diethylamino)benzophenone.
  • alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy Examples include anthracene, 2-ethyl-9,10-dibutoxyanthracene, and the like.
  • Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
  • carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.
  • the content thereof is preferably 0.1 to 30 parts by mass, more preferably 0.1 to 30 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). Preferably it is 1 to 20 parts by mass.
  • the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of optical filters tends to improve.
  • the solvent (E) is not particularly limited, and any solvent commonly used in the field can be used.
  • any solvent commonly used in the field can be used.
  • ester solvents solvents that contain -COO- but no -O- in the molecule
  • ether solvents solvents that contain -O- but no -COO- in the molecule
  • ether ester solvents solvents that contain -O- but no -COO- in the molecule
  • solvents containing -COO- and -O- solvents containing -COO- and -O-
  • ketone solvents solvents containing -CO- in the molecule but not -COO-
  • alcohol solvents solvents containing OH in the molecule, -O-, - (CO- and -COO--free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.
  • Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and ⁇ -butyrolactone.
  • Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether.
  • propylene glycol monopropyl ether propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl
  • examples include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, and methylanisole.
  • Ether ester solvents include methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl
  • Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. etc.
  • alcohol solvents examples include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
  • aromatic hydrocarbon solvents examples include benzene, toluene, xylene, and mesitylene.
  • amide solvent examples include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
  • the solvent (E) is preferably at least one selected from the group consisting of ether ester solvents and ether solvents, and more preferably propylene glycol monomethyl ether acetate or diethylene glycol ethyl methyl ether.
  • the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored resin composition.
  • the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass, based on the total amount of the colored resin composition.
  • the content of the ether ester solvent is preferably 10 to 100% by mass, more preferably 15 to 90% by mass, and even more preferably 17 to 80% by mass, based on the total amount of the solvent. .
  • the content of the ether solvent is preferably 20 to 90% by mass, more preferably 30 to 85% by mass, and even more preferably 40 to 80% by mass, based on the total amount of solvent.
  • Leveling agent (F) examples include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms. These may have a polymerizable group in the side chain.
  • silicone surfactant examples include surfactants having a siloxane bond in the molecule.
  • Toray silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 product name, manufactured by Dow Corning Toray Co., Ltd.
  • KP321, KP322, KP323, KP324 , KP326, KP340, KP341 manufactured by Shin-Etsu Chemical Co., Ltd.
  • TSF400 TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan LLC), etc.
  • fluorine-based surfactant examples include surfactants having a fluorocarbon chain in the molecule.
  • Florado registered trademark
  • FC430 Florado FC431 (manufactured by Sumitomo 3M Ltd.), Megafac (registered trademark) F142D, Florado (registered trademark) F171, Florado F172, Florado F173, Florado F177, Florado F183, Florado F554, Megafac (registered trademark) R30, RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Examples include S382, SC101, SC105 (manufactured by AGC Co., Ltd. (formerly Asahi Glass Co., Ltd.)) and E5844 (manufactured
  • silicone surfactant having a fluorine atom examples include surfactants having a siloxane bond and a fluorocarbon chain in the molecule.
  • a fluorine atom examples include surfactants having a siloxane bond and a fluorocarbon chain in the molecule.
  • Megafac (registered trademark) R08, Megafac (registered trademark) BL20, Megafac (registered trademark) F475, Megafac (registered trademark) F477, and Megafac (registered trademark) F443 manufactured by DIC Corporation
  • the content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and even more preferably 0.002% by mass, based on the total amount of the colored resin composition. 01 to 0.05% by mass. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the optical filter can be improved.
  • the colored resin composition of this embodiment may optionally contain dispersants, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc. known in the technical field. It may contain additives.
  • the colored resin composition of this embodiment is suitably used for transmitting infrared rays.
  • the maximum absorption wavelength in the wavelength range of 380 to 1400 nm is 799 nm or less.
  • the maximum absorption wavelength is preferably 795 nm or less, more preferably 790 nm or less, and even more preferably 785 nm or less.
  • the lower limit of the maximum absorption wavelength is not particularly limited, but may be, for example, 750 nm or more, preferably 755 nm or more, more preferably 760 nm or more, and still more preferably 765 nm or more.
  • the maximum absorption wavelength in the wavelength range of 380 to 1400 nm can be measured using an ultraviolet-visible near-infrared absorption spectrometer (eg, V-770, manufactured by JASCO Corporation).
  • the measurement method can be performed, for example, as follows. First, the colored resin composition is diluted with a solvent (for example, solvent (E) described below) so that the content of the compounds represented by formula (I) and formula (II) becomes 10 mass ppm, and a solution for measurement is prepared. Prepare. The measurement solution thus prepared is placed in a 1 cm square quartz cell, and the spectrum is measured in the wavelength range of 1400 to 300 nm (data sampling interval 1 nm) using an ultraviolet-visible near-infrared absorption spectrometer.
  • a solvent for example, solvent (E) described below
  • the wavelength showing the maximum value of absorbance is defined as the maximum absorption wavelength ⁇ max .
  • the maximum absorption wavelength can be determined.
  • the maximum absorption wavelength tends not to change even when a resin (B), a polymerizable compound (C), a polymerization initiator (D), etc., which will be described later, are present in the measurement solution. Therefore, for example, a solution containing a colorant and a solvent is prepared by removing the resin (B), a polymerizable compound (C), a polymerization initiator (D), etc. described below from a colored resin composition as a measurement solution.
  • the maximum absorption wavelength in the wavelength range of 380 to 1400 nm measured using the method may be regarded as the maximum absorption wavelength in the wavelength range of 380 to 1400 nm of the colored resin composition.
  • the ratio of the absorbance Abs(780) at a wavelength of 780 nm to the absorbance Abs( ⁇ max ) at ⁇ max is, for example, 0.50. It may be more than that. Since the optical filter needs to absorb light in the upper limit of 780 nm in the visible region, the larger this value is, the more preferable it is as a characteristic of the optical filter having near-infrared transmittance. Abs(780)/Abs( ⁇ max ) is preferably 0.60 or more, more preferably 0.70 or more, and still more preferably 0.75 or more. The upper limit of Abs(780)/Abs( ⁇ max ) may be, for example, 1.00 or less.
  • the ratio of the maximum absorbance Abs (900-1400) in the wavelength range of 900 to 1400 nm and the absorbance Abs ( ⁇ max ) at ⁇ max (Abs (900-1400)/Abs ( ⁇ max ) )) may be, for example, 0.30 or less.
  • Abs(900-1400)/Abs( ⁇ max ) is preferably 0.25 or less, more preferably 0.20 or less, even more preferably 0.16 or less.
  • the lower limit of Abs(900-1400)/Abs( ⁇ max ) may be, for example, 0.01 or more or 0.03 or more.
  • the colored resin composition of the present embodiment includes, for example, a colorant (A), a resin (B), a solvent (E), a polymerizable compound (C) used as necessary, a polymerization initiator (D), It can be prepared by mixing the leveling agent (F), the polymerization initiation aid (D1), and other components.
  • a colored dispersion or a pigment dispersion containing the colorant (A1) may be prepared.
  • the desired colored resin composition can be prepared by mixing the remaining components with the colored dispersion or pigment dispersion to a predetermined concentration.
  • the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution.
  • the solution is preferably filtered through a filter with a pore size of approximately 0.01 to 1 ⁇ m.
  • the colored resin composition is preferably filtered through a filter with a pore size of about 0.01 to 10 ⁇ m after mixing each component.
  • Examples of methods for producing a colored pattern from the colored resin composition of this embodiment include a photolithography method, an inkjet method, and a printing method.
  • the method for producing the colored pattern is preferably a photolithography method.
  • the photolithography method is a method in which a colored resin composition is applied to a substrate, dried to form a colored coating film, and the colored coating film is exposed to light through a photomask and developed.
  • a colored cured coating film which is a cured product of a colored coating film, can be formed.
  • the colored pattern or colored cured coating film thus formed is the optical filter of this embodiment.
  • the film thickness of the optical filter to be produced is not particularly limited, and can be adjusted as appropriate depending on the purpose, use, etc.
  • the thickness of the optical filter may be, for example, 0.1 to 30 ⁇ m, preferably 0.1 to 20 ⁇ m, and more preferably 0.5 to 6 ⁇ m.
  • Substrates include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass whose surface is coated with silica; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon substrates; Examples include substrates on which thin films of aluminum, silver, silver/copper/palladium alloys, etc. are formed. Other optical filters (colored patterns or colored cured coatings), resin films, transistors, circuits, etc. may be formed on these substrates.
  • Formation of each color pixel by photolithography can be performed using known or commonly used equipment and conditions. Pixels of each color can be formed by the photolithography method, for example, as described below.
  • a colored resin composition is applied onto a substrate and dried by heat drying (pre-baking) and/or vacuum drying to remove volatile components such as solvents and drying to obtain a smooth colored coating film.
  • Coating methods include spin coating, slit coating, slit and spin coating, and the like.
  • the temperature for heat drying is preferably 30 to 120°C, more preferably 50 to 110°C. Further, the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure is performed, it is preferably carried out under a pressure of 50 to 150 Pa and at a temperature of 20 to 25°C.
  • the thickness of the colored coating film is not particularly limited, and can be appropriately selected depending on the thickness of the intended optical filter.
  • the colored coating film is exposed to light through a photomask to form a desired colored pattern.
  • the pattern on the photomask is not particularly limited, and a pattern depending on the intended use is used.
  • the light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm.
  • the light source used for exposure may be one that cuts light of less than 350 nm using a filter that cuts this wavelength range, and light of around 436 nm, around 408 nm, and around 365 nm can be cut out in these wavelength ranges.
  • a bandpass filter may be used to selectively extract the .
  • Specific examples of light sources used for exposure include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.
  • the entire exposed surface can be uniformly irradiated with parallel light, and the photomask and the substrate on which the colored coating film is formed can be accurately aligned, making it possible to use mask aligners, steppers, etc. for exposure.
  • a device is used.
  • a colored pattern is formed on the substrate by bringing the exposed colored coating film (that is, colored cured coating film) into contact with a developer and developing it.
  • the unexposed areas of the colored composition layer are dissolved in a developer and removed.
  • the developer include aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, and tetramethylammonium hydroxide.
  • the concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.
  • the developer may further contain a surfactant.
  • Development methods include paddle method, dipping method, spray method, and the like. During development, the substrate may be tilted at any angle. Moreover, after development, it is preferable to wash the obtained colored pattern with water.
  • the obtained colored pattern is preferably post-baked.
  • the post-bake temperature is preferably 150-250°C, more preferably 160-235°C.
  • the post-bake time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.
  • Solid-state image sensor The solid-state imaging device of this embodiment includes an optical filter that is a colored pattern, a colored cured coating, or the like.
  • an infrared transmission filter can be produced.
  • the infrared transmission filter is useful as a film used in display devices (eg, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.
  • the absorbance and maximum absorption wavelength were confirmed using an ultraviolet-visible near-infrared absorption spectrometer (V-770 manufactured by JASCO Corporation, slit width: 1 nm).
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC method under the following conditions.
  • Detector RI
  • Calibration standard material TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
  • the ratio of the weight average molecular weight and number average molecular weight (Mw/Mn) in terms of polystyrene obtained above was defined as the degree of dispersion.
  • reaction solution was poured into 15,000 parts of pure water, and liquid-liquid extraction was performed three times with 5,000 parts of methylene chloride.
  • the separated organic layer was dehydrated with anhydrous sodium sulfate (manufactured by Kanto Kagaku Co., Ltd.), the sodium sulfate was filtered, and the solvent was distilled off.
  • the crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 17 parts of the compound represented by formula (Ib) as pale yellow crystals (yield 51%).
  • reaction solution was cooled to room temperature (18-24°C) and poured into 8000 parts of methanol.
  • the precipitated solid was washed by decantation twice with 200 parts of ion-exchanged water and twice with 200 parts of methanol.
  • the crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 5.3 parts (yield 59%) of compound (II-1) represented by formula (II-1) as a solid. .
  • Phthalocyanine compound Pc-02 was obtained according to the synthesis method described in Example 1 of JP-A-2014-19838.
  • Example 1 (1) Preparation of colored resin composition 1A 30 parts of compound (I-1) as colorant (A), 24 parts of dispersant (manufactured by BYK, BYKLPN-6919) (in terms of solid content), synthesized as resin (B) 24 parts of the resin (B-1) (solid content) obtained in Example 10, 522 parts of propylene glycol monomethyl ether acetate as the solvent (E), and 900 parts of 0.2 mm zirconia beads were mixed, and paint conditioner (LAU Co., Ltd.) was mixed. The resulting mixture was shaken for 1 hour using a commercially available product. Thereafter, the zirconia beads were removed by filtration to obtain colored resin composition 1A.
  • compound (I-1) as colorant (A) 24 parts of dispersant (manufactured by BYK, BYKLPN-6919) (in terms of solid content)
  • resin (B) 24 parts of the resin (B-1) (solid content) obtained in Example 10
  • E propylene glyco
  • the ratio (Abs(780)/Abs( ⁇ max )) between the absorbance Abs(780) at a wavelength of 780 nm and the absorbance Abs( ⁇ max ) at ⁇ max was calculated. Since the optical filter needs to absorb light in the upper limit of 780 nm in the visible region, the larger this value is, the more preferable it is as a characteristic of the optical filter having near-infrared transmittance. In addition, the ratio (Abs(900-1400)/Abs( ⁇ max )) between the maximum absorbance Abs (900-1400) in the wavelength range of 900 to 1400 nm and the absorbance Abs ( ⁇ max ) at ⁇ max was calculated. The smaller this value is, the higher the transmittance in the near-infrared region and the higher the sensitivity as a sensor, which is preferable as a characteristic of an optical filter having near-infrared transmittance.
  • Colored resin composition 1B was applied onto a 5 cm square glass substrate (Eagle 2000, manufactured by Corning Inc.) by a spin coating method to obtain a colored coating film. Thereafter, the colored coating film was prebaked at 100°C for 3 minutes, and postbaked in an oven at 230°C for 20 minutes to obtain a colored cured coating film.
  • UV cut filter (COLORED OPTICAL GLASS L38, manufactured by Hoya Corporation, a filter that cuts light of 380 nm or less) was placed on the obtained colored cured coating film, and a light resistance tester (SUNTEST CPS+, (manufactured by Toyo Seiki Seisakusho Co., Ltd.) was irradiated with xenon lamp light for 68 hours, and the absorbance retention rate of the colored cured coating before and after irradiation was measured.
  • the absorbance maintenance rate is a numerical value calculated from the following formula, and means that the higher the absorbance retention rate is, the better the light resistance is.
  • Example 2 Colored resin composition 2A and colored resin composition 2B were obtained in the same manner as in Example 1, except that 30 parts of compound (II-1) was replaced with 30 parts of compound (II-1). A colored cured coating film was prepared. The colored resin composition 2A and the colored cured coating film were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • Example 3 Colored resin composition 3A and colored resin composition 3B were obtained in the same manner as in Example 1, except that 30 parts of compound (II-2) was used instead of 30 parts of compound (I-1). A colored cured coating film was prepared. The colored resin composition 3A and the colored cured coating were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • Example 4 A colored resin composition was prepared in the same manner as in Example 1, except that 30 parts of compound (I-1) was replaced with 15 parts of compound (I-1) and 15 parts of compound (II-1). 4A and colored resin composition 4B were obtained, and a colored cured coating film was produced. The colored resin composition 4A and the colored cured coating film were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • Example 5 A colored resin composition was prepared in the same manner as in Example 1, except that 30 parts of compound (I-1) was replaced with 6 parts of compound (I-1) and 24 parts of compound (II-1). 5A and colored resin composition 5B were obtained, and a colored cured coating film was produced. The colored resin composition 5A and the colored cured coating film were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • Example 6> A colored resin composition was prepared in the same manner as in Example 1, except that 30 parts of compound (I-1) was replaced with 10 parts of compound (I-1) and 20 parts of compound (II-1). 6A and colored resin composition 6B were obtained, and a colored cured coating film was produced. The colored resin composition 6A and the colored cured coating film were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • Example 7 A colored resin composition was prepared in the same manner as in Example 1, except that 30 parts of compound (I-1) was replaced with 20 parts of compound (I-1) and 10 parts of compound (II-1). 7A and colored resin composition 7B were obtained, and a colored cured coating film was produced. The colored resin composition 7A and the colored cured coating film were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • Colored resin composition 1a and colored resin composition 1b were obtained in the same manner as in Example 1, except that 30 parts of compound (I-1) was replaced with 30 parts of phthalocyanine compound Pc-02, A colored cured coating film was prepared.
  • the colored resin composition 1a and the colored cured coating were subjected to ultraviolet-visible near-infrared absorption spectroscopy, heat resistance test, and light resistance test in the same manner as in Example 1. The results are shown in Table 1.
  • the colored cured coatings of Examples 1 to 7 containing the predetermined colorant have better heat resistance and light resistance than the colored cured coating of Comparative Example 1 that does not contain the predetermined colorant. It was excellent. From these results, it was confirmed that the colored resin composition of the present invention can form an optical filter with excellent heat resistance.

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Abstract

La présente invention aborde le problème de la fourniture d'une composition de résine colorée qui est capable de former un filtre optique qui a une excellente résistance à la chaleur.　La présente invention concerne une composition de résine colorée qui contient un agent colorant, une résine soluble dans les alcalis et un solvant. L'agent colorant contient au moins un composé qui est choisi dans le groupe constitué par les composés représentés par la formule (I) et la formule (II). La longueur d'onde d'absorption maximale dans la plage de longueurs d'onde de 380 nm à 1 400 nm est inférieure ou égale à 799 nm. (Dans la formule (I), M1 représente un atome de métal divalent ; chacun de R1 à R8 représente un groupe hydrocarboné ayant de 1 à 20 atomes de carbone, ou similaire ; R17 représente un groupe hydrocarboné ayant de 1 à 20 atomes de carbone, ou similaire ; et chacun de A1 à A8 représente un groupe aryle ayant de 6 à 20 atomes de carbone, ou similaire.)　(Dans la formule (II), M2 représente un atome de métal divalent ; chacun de R9 à R16 représente un groupe hydrocarboné saturé ayant de 1 à 10 atomes de carbone ; et chacun de A9 à A16 représente un groupe aryle ayant de 6 à 20 atomes de carbone, ou similaire.)
PCT/JP2023/019511 2022-06-16 2023-05-25 Composition de résine colorée, filtre optique et élément d'imagerie à semi-conducteurs Ceased WO2023243353A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070010645A1 (en) * 2005-07-05 2007-01-11 Silverbrook Research Pty Ltd Red-shifted water dispersible IR dyes
JP2007099840A (ja) * 2005-09-30 2007-04-19 Fujifilm Corp 着色硬化性組成物、カラーフィルタおよびその製造方法
JP2009051774A (ja) * 2007-08-28 2009-03-12 Univ Nihon フタロシアニン化合物
JP2011241349A (ja) * 2010-05-21 2011-12-01 Fujifilm Corp 硬化性インキ組成物、記録物、画像記録方法、及び画像検出方法
JP2011241332A (ja) * 2010-05-19 2011-12-01 Fujifilm Corp 赤外線吸収性組成物、赤外線吸収性インキ、記録物、画像記録方法、及び画像検出方法

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Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070010645A1 (en) * 2005-07-05 2007-01-11 Silverbrook Research Pty Ltd Red-shifted water dispersible IR dyes
JP2007099840A (ja) * 2005-09-30 2007-04-19 Fujifilm Corp 着色硬化性組成物、カラーフィルタおよびその製造方法
JP2009051774A (ja) * 2007-08-28 2009-03-12 Univ Nihon フタロシアニン化合物
JP2011241332A (ja) * 2010-05-19 2011-12-01 Fujifilm Corp 赤外線吸収性組成物、赤外線吸収性インキ、記録物、画像記録方法、及び画像検出方法
JP2011241349A (ja) * 2010-05-21 2011-12-01 Fujifilm Corp 硬化性インキ組成物、記録物、画像記録方法、及び画像検出方法

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