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WO2012102395A1 - Composition colorée pour filtres colorés, et filtre coloré - Google Patents

Composition colorée pour filtres colorés, et filtre coloré Download PDF

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Publication number
WO2012102395A1
WO2012102395A1 PCT/JP2012/051881 JP2012051881W WO2012102395A1 WO 2012102395 A1 WO2012102395 A1 WO 2012102395A1 JP 2012051881 W JP2012051881 W JP 2012051881W WO 2012102395 A1 WO2012102395 A1 WO 2012102395A1
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WIPO (PCT)
Prior art keywords
group
pigment
substituent
color filter
parts
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/JP2012/051881
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English (en)
Japanese (ja)
Inventor
北村　健一
理人 伊藤
貴子 藤田
裕介 飯田
章乃 宮川
侑紀 山田
俊啓 吉沢
由昌 宮沢
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.)
Toyochem Co Ltd
Artience Co Ltd
Original Assignee
Toyo Ink SC Holdings Co Ltd
Toyochem Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP2011015873A external-priority patent/JP4893859B1/ja
Priority claimed from JP2011118730A external-priority patent/JP5699293B2/ja
Priority claimed from JP2011118728A external-priority patent/JP5724117B2/ja
Priority claimed from JP2011118727A external-priority patent/JP5732704B2/ja
Priority claimed from JP2011118729A external-priority patent/JP5699292B2/ja
Priority claimed from JP2011219021A external-priority patent/JP5764805B2/ja
Priority claimed from JP2011231307A external-priority patent/JP5764806B2/ja
Priority to KR1020137020921A priority Critical patent/KR101819582B1/ko
Priority to CN201280006719.5A priority patent/CN103370642B/zh
Application filed by Toyo Ink SC Holdings Co Ltd, Toyochem Co Ltd filed Critical Toyo Ink SC Holdings Co Ltd
Publication of WO2012102395A1 publication Critical patent/WO2012102395A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
    • C09B67/0064—Preparation of organic pigments of organic pigments with only macromolecular substances of phthalocynanines with only macromolecular substances
    • 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
    • C09B47/10—Obtaining compounds having halogen 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
    • C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, 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
    • C09B47/18—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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/22—Obtaining compounds having nitrogen 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/007—Dyestuffs containing phosphonic or phosphinic acid groups and derivatives
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • 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

Definitions

  • the present invention relates to a color filter coloring composition and a color filter.
  • a liquid crystal layer sandwiched between two polarizing plates controls the amount of light passing through the first polarizing plate by controlling the degree of polarization of light passing through the first polarizing plate.
  • a display device that performs display As such a device, a type using a twisted nematic (TN) type liquid crystal has become the mainstream.
  • the liquid crystal display device can perform color display by providing a color filter between two polarizing plates. Since such a liquid crystal display device has recently been used in televisions, personal computer monitors, and the like, there is an increasing demand for high contrast, high brightness, and high color reproducibility for color filters.
  • IPS in-plane switching
  • VA alignment
  • OBC optically-conventional-bend
  • a color filter is a surface of a transparent substrate such as glass, in which two or more kinds of fine band (striped) filter segments of different hues are arranged in parallel or crossing each other, or fine filter segments are arranged vertically and horizontally. It is made up of those arranged in Generally, it is often formed of three color filter segments of red, green, and blue. Each segment is as fine as several microns to several hundred microns, and is arranged in a predetermined arrangement for each hue.
  • a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering. Furthermore, an alignment film for aligning the liquid crystal in a certain direction is formed thereon.
  • the formation thereof must generally be performed at a high temperature of 200 ° C. or higher, preferably 230 ° C. or higher. For this reason, at present, as a method for producing a color filter, a method called a pigment dispersion method using a pigment having excellent heat resistance and light resistance as a colorant is mainly used.
  • the production method of the filter segment constituting the color filter is as follows. First, a photosensitive material is applied to a glass substrate or the like, and excess solvent is removed by drying. Then, active energy rays are irradiated by proximity exposure (ultraviolet light source exposure) or the like through a photomask for pixel formation, and curing (negative type) or alkali solubility is increased (positive type). Next, the part which melt
  • Patent Document 1 proposes a composition for a color filter using a halogenated phthalocyanine compound substituted with at least four halogen atoms as a green colorant.
  • a halogenated copper phthalocyanine pigment and a central metal are selected from the group consisting of Mg, Al, Si, Ti, V, Mn, Fe, Co, Ni, Zn, Ge, and Sn.
  • a composition for a color filter comprising a green colorant comprising at least one kind of halogenated dissimilar metal phthalocyanine pigment.
  • Patent Document 3 discloses a pigment composition that maintains a clear hue, high light resistance, and high heat resistance by using a blue aluminum phthalocyanine pigment containing no halogen and a green pigment containing halogen. Yes.
  • Patent Document 4 an aluminum phthalocyanine pigment is used as a main pigment, high brightness is obtained with a high chromaticity even with a relatively small content, and both color density and color purity are achieved. Technology is disclosed.
  • Patent Documents 5 and 6 disclose monomeric aluminum phthalocyanine pigments in which the shaft material is a phosphoric acid compound or a silanol compound.
  • Patent Document 7 discloses a bis (phthalocyanylaluminum) tetraphenyldisiloxane pigment obtained by dimerizing an aluminum phthalocyanine pigment with diphenylchlorosilane or a bis (phthalocyanylaluminum) phenylphosphonate pigment dimerized using phenylphosphonic acid. Is disclosed.
  • the pigment compositions containing these aluminum phthalocyanine compounds have insufficient heat resistance at 230 ° C. or higher and long-term light resistance, which are required for color filter applications. For this reason, there is a problem that the spectral shape changes. Furthermore, there are problems such as an increase in viscosity of the coloring composition due to poor dispersibility and generation of foreign matter (mainly due to crystallization of phthalocyanine) on the coating film.
  • the quality item required for the color filter includes brightness as described above.
  • the light transmittance is low, resulting in a dark screen.
  • color liquid crystal devices have been used for televisions, personal computer monitors, etc.
  • color filters are required to have high lightness and high reliability (heat resistance, light resistance). .
  • a voltage holding ratio can be given as an index representing the display performance of the liquid crystal display device.
  • Liquid crystal is an extremely high insulating material, and when the polar compound remaining in the color filter coloring composition elutes into the liquid crystal cell, the voltage between the electrodes decreases, leading to a decrease in voltage holding ratio, and display unevenness. Generation
  • a green coloring composition for a color filter containing an aluminum phthalocyanine pigment and a yellow pigment (Patent Document 4), or a color filter containing a phthalocyanine dye having various structures and a quinophthalone dye.
  • a green coloring composition (Patent Documents 9 to 11) and the like have been proposed.
  • these green coloring compositions for color filters have a problem that lightness is insufficient.
  • the materials used as a material for curing are limited. Furthermore, in order to increase photocurability, if the components such as photopolymerization initiator and photopolymerizable monomer are increased, yellowing occurs in the post-baking process at 230 ° C or more, and the brightness of the green filter segment is reduced. There was a problem of becoming a factor to make it.
  • Embodiments of the present invention relate to the following (1) to (15).
  • X 1 to X 4 are each independently an alkyl group which may have a substituent, an aryl group which may have a substituent, or a cycloalkyl group which may have a substituent.
  • a heterocyclic group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent Represents an arylthio group which may have Y 1 to Y 4 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group, M represents Al, Z represents —OP ( ⁇ O) R 1 R 2 , and R 1 and R 2 each independently have a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, or a substituent.
  • the colorant further contains C.I.
  • the coloring composition for a color filter according to (1) comprising a yellow pigment selected from the group consisting of CI Pigment Yellow 185.
  • the colored composition for a color filter according to (1) further comprising a component selected from the group consisting of a photopolymerizable monomer and a photopolymerization initiator.
  • the color filter coloring composition according to (1) wherein the colorant further contains a pigment having an acidic group amount of 100 to 600 ⁇ mol / g.
  • the pigment having an acidic group amount of 100 to 600 ⁇ mol / g is C.I. I.
  • the coloring composition for a color filter which is a pigment selected from the group consisting of CI Pigment Yellow 139.
  • the coloring composition for a color filter according to (1) further comprising a basic resin dispersant having an amine value of 10 to 300 mgKOH / g.
  • the binder resin is a vinyl resin in which an ethylenically unsaturated double bond is introduced using an ethylenically unsaturated monomer having an epoxy group, and the structural unit (b1) has the following ratio:
  • a coloring composition for a color filter according to (1) which comprises a vinyl resin [B1] containing the structural unit (b2).
  • R 4 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a benzene ring.
  • the vinyl resin [B1] is obtained by reacting the precursor of the structural unit (b2) with an ethylenically unsaturated monomer having an epoxy group to obtain a copolymer (i1-1).
  • the obtained copolymer (i1-1) is reacted with an unsaturated monobasic acid to obtain a copolymer (i1-2). Further, the obtained copolymer (i1-2) Or a polybasic acid anhydride, or a copolymer (i2-1) obtained by reacting a precursor of the structural unit (b1) with a precursor of the structural unit (b2).
  • the colored composition for color filters of (8) which is a resin obtained by reacting the obtained copolymer (i2-1) with an ethylenically unsaturated monomer having an epoxy group .
  • the antioxidant is an antioxidant selected from the group consisting of a hindered phenol-based antioxidant, a hindered amine-based antioxidant, a phosphorus-based antioxidant, and a sulfur-based antioxidant.
  • Phthalocyanine (A): represented by the following formula (12), and an X-ray diffraction pattern by CuK ⁇ rays shows a black angle 2 ⁇ ( ⁇ 0.2) 7.7 °, 8.4 °, 9.3 °, 12 .7 °, 15.0 °, 15.9 °, 16.7 °, 18.8 °, 20.1 °, 21.7 °, 23.1 °, 25.4 °, 26.5 °, 28 A phthalocyanine compound having a peak at 2 °.
  • Phthalocyanine (C): represented by the following formula (13), and an X-ray diffraction pattern by CuK ⁇ rays shows a black angle 2 ⁇ ( ⁇ 0.2) 5.0 °, 7.1 °, 8.6 °, 9 Phthalocyanine compounds having peaks at .8 °, 11.7 °, 14.7 °, 16.5 ° and 25.0 °.
  • a color filter comprising a filter segment formed on the base material from the color filter coloring composition according to any one of (1) to (14).
  • the problem of embodiment I is to provide a coloring composition for a color filter which is excellent in heat resistance and light resistance and does not generate foreign matter on the coating film.
  • the subject of further embodiment I is to provide a color filter capable of high brightness and a wide color reproduction region by using the photosensitive coloring composition for a color filter using the above coloring composition.
  • a coloring composition for a color filter containing a phthalocyanine compound having a specific structure is excellent in heat resistance and light resistance, and at the same time.
  • the present invention has been made based on the finding that it has lightness and this knowledge.
  • Embodiment I A color filter coloring composition comprising at least a colorant, a binder resin, and an organic solvent, wherein the colorant contains a phthalocyanine compound represented by the following formula (1):
  • a coloring composition for a color filter [Wherein, X 1 to X 4 are each independently an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, or a substituent.
  • Y 1 to Y 4 each independently represents a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • M represents Al.
  • Z represents —OP ( ⁇ O) R 1 R 2 , wherein R 1 and R 2 each independently have a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, or a substituent.
  • the yellow pigment is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, and C.I. I.
  • (I-5) The colored composition for a color filter as described in any one of (I-1) to (I-4), further comprising a photopolymerizable monomer and / or a photopolymerization initiator.
  • At least one green filter segment is represented by (I-1) to (I-5)
  • the color filter is excellent in heat resistance and light resistance and does not generate foreign matter on the coating film.
  • a colored composition can be provided.
  • a color filter capable of high brightness and a wide color reproduction region can be provided by the photosensitive coloring composition for a color filter using the above coloring composition.
  • Embodiment II relates to Embodiment II.
  • Embodiment II has excellent dispersibility and dispersion stability, and further, when used in a color filter, a color composition for color filter that does not cause a decrease in contrast ratio over time, a photosensitive color composition, And providing a color filter using the same.
  • Embodiment II Specific examples of Embodiment II are as follows.
  • (II-1) A color filter coloring composition comprising a colorant, a binder resin, and an organic solvent, wherein the colorant comprises an aluminum phthalocyanine pigment represented by formula (2) or formula (3) and an acidic group
  • a coloring composition for a color filter comprising a pigment in an amount of 100 to 600 ⁇ mol / g.
  • X 1 to X 4 are each independently an alkyl group that may have a substituent, an aryl group that may have a substituent, or a cycloalkyl that may have a substituent.
  • Y 1 to Y 4 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • Z represents —OP ( ⁇ O) R 1 R 2 or —O—SiR 3 R 4 R 5 .
  • R 1 to R 5 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, or an alkoxyl group which may have a substituent. Or an aryloxy group which may have a substituent, and Rs may be bonded to each other to form a ring.
  • m 1 to m 4 and n 1 to n 4 each independently represent an integer of 0 to 4, and m 1 + n 1 , m 2 + n 2 , m 3 + n 3 , m 4 + n 4 are each 0 to 4 may be the same or different.
  • X 5 to X 12 are each independently an alkyl group which may have a substituent, an aryl group which may have a substituent, or a cycloalkyl which may have a substituent.
  • Group, a heterocyclic group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent Represents an arylthio group which may have a group.
  • Y 5 to Y 12 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • L represents —O—SiR 6 R 7 —O—, —O—SiR 6 R 7 —O—SiR 8 R 9 —O—, or —O—P ( ⁇ O) R 10 —O—
  • R 6 to R 10 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, or a substituent.
  • the aryloxy group which may have a group is represented.
  • m 5 to m 12 and n 5 to n 12 each independently represent an integer of 0 to 4, and m 5 + n 5 , m 6 + n 6 , m 7 + n 7 , m 8 + n 8 , m 9 + n 9 , m 10 + n 10 , m 11 + n 11 , and m 12 + n 12 are each 0 to 4, and may be the same or different.
  • a pigment having an acidic group amount of 100 to 600 ⁇ mol / g is C.I. I. Pigment green 58, C.I. I. Pigment yellow 150, and C.I. I.
  • (II-3) The coloring composition for a color filter as described in (II-1) or (II-2), further comprising a basic resin type dispersant having an amine value of 10 to 300 mgKOH / g.
  • (II-4) The coloring composition for a color filter as described in any one of (II-1) to (II-3), which further contains a pigment derivative.
  • a color filter comprising a filter segment formed from the colored composition for color filter according to any one of (II-1) to (II-5) on a substrate. .
  • (II-7) A media-type wet disperser in a pigment carrier containing a colorant containing an aluminum phthalocyanine pigment represented by formula (2) or formula (3) and a pigment having an acidic group content of 100 to 600 ⁇ mol / g.
  • X 1 to X 4 are each independently an alkyl group that may have a substituent, an aryl group that may have a substituent, or a cycloalkyl that may have a substituent.
  • Group, a heterocyclic group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent Represents an arylthio group which may have a group.
  • Y 1 to Y 4 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • Z represents —OP ( ⁇ O) R 1 R 2 or —O—SiR 3 R 4 R 5 .
  • R 1 to R 5 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, or an alkoxyl group which may have a substituent. Or an aryloxy group which may have a substituent, and Rs may be bonded to each other to form a ring.
  • n 1 to m 4 and n 1 to n 4 each independently represent an integer of 0 to 4, and m 1 + n 1 , m 2 + n 2 , m 3 + n 3 , m 4 + n 4 are each 0 to 4 may be the same or different.
  • X 5 to X 12 are each independently an alkyl group which may have a substituent, an aryl group which may have a substituent, or a cycloalkyl which may have a substituent.
  • Y 5 to Y 12 each independently represent a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • L represents —O—SiR 6 R 7 —O—, —O—SiR 6 R 7 —O—SiR 8 R 9 —O—, or —O—P ( ⁇ O) R 10 —O—
  • R 6 to R 10 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, or a substituent.
  • the aryloxy group which may have a group is represented.
  • n 5 to m 12 and n 5 to n 12 each independently represent an integer of 0 to 4, and m 5 + n 5 , m 6 + n 6 , m 7 + n 7 , m 8 + n 8 , m 9 + n 9 , m 10 + n 10 , m 11 + n 11 , and m 12 + n 12 are each 0 to 4, and may be the same or different.
  • a color filter coloring composition a photosensitive color composition, and a color filter using the same, which have excellent dispersion stability and do not cause a decrease in contrast ratio over time when used in a color filter. can do.
  • Formula (2) is the same formula as formula (1), although the method for describing substituents is different.
  • Embodiment III relates to Embodiment III.
  • the problem of the embodiment III is to provide a coloring composition for a color filter having a high contrast ratio and good heat resistance, and a color filter using the same.
  • the color composition for color filters has an excellent balance of performance necessary for forming good filter segments, such as pattern shape and resolution, and contrast ratio using the same.
  • the object is to provide an excellent, high-definition color filter.
  • Embodiment III A color filter coloring composition comprising a colorant, a binder resin, and an organic solvent, wherein the colorant contains a phthalocyanine dye represented by the following formula (4), and the binder resin: Is a vinyl resin in which an ethylenically unsaturated double bond is introduced using an ethylenically unsaturated monomer having an epoxy group, and a vinyl resin containing the following structural units (b1) and (b2) [ B1] is contained, The coloring composition for color filters characterized by the above-mentioned.
  • a 1 to A 16 each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
  • R 1 and R 2 are each independently hydrogen atom, hydroxy group, an optionally substituted alkyl group, an optionally substituted aryl group, or an -OR 3, and R 1 R 2 may be bonded to each other to form a ring.
  • R 3 is an alkyl group which may have a substituent, or an aryl group which may have a substituent.
  • (III-3) The coloring composition for a color filter as described in (III-1) or (III-2), wherein the vinyl resin [B1] further contains the following structural unit (b3). (B3); a structural unit having an aliphatic cyclic group represented by formula (8) or formula (9): 2 to 60% by weight based on the weight of all structural units of the vinyl resin [B1] (III-4)
  • III-5) A color filter comprising a filter segment formed from the colored composition for color filter according to any one of (III-1) to (III-4) on a substrate.
  • the colored composition for color filter of Embodiment III has good patterning suitability in alkali development, and a color filter having a good pattern shape can be obtained.
  • a color filter having a high contrast ratio and good heat resistance can be provided.
  • Formula (4) is the same as formula (1), although the method for describing substituents is different.
  • Embodiment IV relates to Embodiment IV.
  • the embodiment (IV) has good developability and image line-formability, and the coloring composition remains (development residue) on the non-pixel portion on the substrate after development, and the pattern portion is missing and / or peeled off from the pixel portion. It is an object of the present invention to provide a photosensitive coloring composition suitable as a highly productive color filter material and a color filter formed using the same.
  • Embodiment IV A photosensitive coloring composition for a color filter containing a colorant, a binder resin, a photopolymerization initiator, and a photopolymerizable monomer, wherein the colorant is represented by the following formula (4):
  • a 1 to A 16 each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Represents.
  • R 1 and R 2 are each independently hydrogen atom, hydroxy group, an optionally substituted alkyl group, an optionally substituted aryl group, or an -OR 3, and R 1 R 2 may be bonded to each other to form a ring.
  • R 3 is an alkyl group which may have a substituent, or an aryl group which may have a substituent.
  • IV-2 The photosensitive coloring composition for color filters according to (IV-1), wherein the acid group of the polyfunctional monomer having an acid group is a carboxyl group.
  • IV-3 The photosensitive coloring composition for color filters as described in (IV-1) or (IV-2), wherein the photopolymerization initiator contains an oxime ester compound or an acetophenone compound.
  • a color filter comprising a filter segment formed from the photosensitive coloring composition for color filter according to any one of (IV-1) to (IV-3) on a substrate. .
  • the developability and the image line-forming property are good, and the coloring composition remains (development residue) on the non-pixel portion on the substrate after development, and the pattern defect and / or peeling of the pixel portion.
  • a photosensitive coloring composition suitable as a highly productive color filter material and a color filter formed using the same can be provided.
  • the problem of embodiment V is that the color composition for color filter, which has good heat resistance, light resistance, and voltage holding ratio and can suppress the decrease in lightness even in the color filter forming process, and the same It is to provide a color filter.
  • V-1 A photosensitive color composition for a color filter containing a colorant, a binder resin, an antioxidant, a photopolymerization initiator, and a photopolymerizable monomer, wherein the colorant has the following formula ( 4)
  • a 1 to A 16 each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Represents.
  • R 1 and R 2 are each independently hydrogen atom, hydroxy group, an optionally substituted alkyl group, an optionally substituted aryl group, or an -OR 3, and R 1 R 2 may be bonded to each other to form a ring.
  • R 3 is an alkyl group which may have a substituent, or an aryl group which may have a substituent.
  • the antioxidant is at least one antioxidant selected from the group consisting of a hindered phenol antioxidant, a hindered amine antioxidant, a phosphorus antioxidant, and a sulfur antioxidant.
  • the coloring composition for color filter of Embodiment V By using the coloring composition for color filter of Embodiment V, the heat resistance, the light resistance, and the voltage holding ratio are good, and the coloring for the color filter that can suppress the decrease in lightness in the color filter forming step.
  • a composition and a color filter using the composition can be provided.
  • embodiment VI when used as a colored composition, aluminum phthalocyanine as a colorant that is excellent in heat resistance and light resistance when used as a colored composition and has very little foreign matter generation in the coating film is used. Is to provide. Moreover, the further subject of this invention is providing the coloring composition which can produce the color filter which has high brightness and wide color reproducibility.
  • the inventors of the present invention have excellent heat resistance and light resistance when an aluminum phthalocyanine having a specific chemical structure and an X-ray diffraction pattern is used as a coloring composition, and foreign matter is generated in the coating film. Has been found to have properties as an extremely small colorant, leading to the present invention.
  • Embodiment VI Specific examples of Embodiment VI are as follows.
  • (VI-4) Furthermore, the aluminum phthalocyanine produced by the production method described in (VI-3) is heat-treated at a temperature of 80 ° C. or higher, and the production of the aluminum phthalocyanine represented by the above formula (12) Method.
  • (VI-6) Aluminum phthalocyanine represented by the above formula (12) produced by the production method described in (VI-3) or (VI-4).
  • (VI-7) A coloring composition comprising at least a binder resin and aluminum phthalocyanine according to any one of (VI-1), (VI-2), and (VI-5).
  • (VI-8) The colored composition according to (VI-7), further comprising a yellow colorant.
  • (VI-9) The coloring composition according to (VI-7) or (VI-8), further comprising a photopolymerizable monomer.
  • a color filter comprising a filter segment formed of the colored composition according to any one of (VI-6) to (VI-8) on a substrate.
  • Embodiment VI by using the aluminum phthalocyanine represented by the formula (12) showing a specific X-ray diffraction pattern, the coloring composition is excellent in heat resistance and light resistance and generates very little foreign matter in the coating film. Can be provided. Moreover, the color filter which gives high brightness and wide color reproducibility can be provided using said coloring composition.
  • Embodiment VII when used as a colored composition, aluminum phthalocyanine as a colorant that has excellent heat resistance and light resistance when used as a colored composition and generates very little foreign matter in the coating film is used. Is to provide. Moreover, the further subject of this invention is providing the coloring composition which can produce the color filter which has high brightness and wide color reproducibility.
  • the inventors of the present invention have excellent heat resistance and light resistance when an aluminum phthalocyanine having a specific chemical structure and an X-ray diffraction pattern is used as a coloring composition, and foreign matter is generated in the coating film. Has been found to have properties as an extremely small colorant, leading to the present invention.
  • a method for producing aluminum phthalocyanine characterized by having a peak (VII-6) Aluminum phthalocyanine represented by the above formula (13) produced by the production method described in (VII-3) or (VIII-4). (VII-7) A coloring composition comprising at least a binder resin and aluminum phthalocyanine according to any one of (VII-1), (VII-2), and (VII-6). (VII-8) The coloring composition according to (VII-7), further comprising a yellow coloring agent. (VII-9) The coloring composition according to (VII-7) or (VII-8), further comprising a photopolymerizable monomer. (VII-10) A color filter comprising a filter segment formed from the colored composition according to any one of (VII-7) to (VII-9) on a substrate.
  • Japanese Patent Application No. 2011-015873 filed on January 28, 2011, Japanese Patent Application No. 2011-118727 filed on May 27, 2011, and Japanese Patent Application Nos. 2011-118728 and 2011 filed on May 27, 2011.
  • Japanese Patent Application No. 2011-118729 filed on May 27, 2011, Japanese Patent Application No. 2011-118730 filed on May 27, 2011, Japanese Patent Application No. 2011-219021 filed on October 3, 2011, and October 21, 2011
  • Japanese Patent Application No. 2011-231307 which are incorporated herein in their entirety for reference.
  • FIG. 1 is an X-ray diffraction pattern of phthalocyanine (B) produced in Examples VI-1 to VI-5 by CuK ⁇ rays.
  • FIG. 2 is an X-ray diffraction pattern of the phthalocyanine (A) produced in Examples VI-6 to 8 using CuK ⁇ rays.
  • FIG. 3 is an X-ray diffraction pattern of hydroxyaluminum phthalocyanine produced in Production Example VI-1 by CuK ⁇ rays.
  • FIG. 4 is an X-ray diffraction pattern of the phthalocyanine (D) produced in Examples VII-1 to 5 by CuK ⁇ ray.
  • FIG. 5 is an X-ray diffraction pattern of the phthalocyanine (C) produced in Examples VII-6 to 8 by CuK ⁇ rays.
  • FIG. 6 is an X-ray diffraction pattern of hydroxyaluminum phthalocyanine produced in Production Example VII-1 by CuK ⁇ rays.
  • One embodiment of the color filter coloring composition contains a colorant, a binder resin, and an organic solvent, and the colorant contains a phthalocyanine compound represented by the following formula (1).
  • each of X 1 to X 4 independently represents an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, or a substituent.
  • a heterocyclic group that may have, an alkoxyl group that may have a substituent, an aryloxy group that may have a substituent, an alkylthio group that may have a substituent, or a substituent Represents an optionally substituted arylthio group.
  • Y 1 to Y 4 each independently represents a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group, or an optionally substituted sulfamoyl group.
  • M represents Al.
  • Z represents —OP ( ⁇ O) R 1 R 2 or —O—SiR 3 R 4 R 5 , wherein R 1 to R 5 may each independently have a hydrogen atom, a hydroxyl group, or a substituent. It represents an alkyl group, an aryl group that may have a substituent, an alkoxyl group that may have a substituent, or an aryloxy group that may have a substituent. It may be formed.
  • m 1 , m 2 , m 3 , m 4 , n 1 , n 2 , n 3 , and n 4 each independently represents an integer of 0 to 4.
  • m 1 + n 1 , m 2 + n 2 , m 3 + n 3 , and m 4 + n 4 are each 0 to 4, and may be the same or different.
  • the colorant contains a phthalocyanine compound represented by the above formula (1).
  • the preferred colorant content in all the non-volatile components of the color filter coloring composition is 10 to 90% by weight, more preferably 15 to 85% by weight from the viewpoint of sufficient color reproducibility and stability. Most preferably, it is 20 to 80% by weight.
  • the pigment content is 10% by weight or more, sufficient color reproducibility is obtained, and when it is 90% by weight or less, the pigment carrier content is sufficient and the stability of the coloring composition is excellent.
  • X 1 to X 4 may be the same or different. Specific examples thereof include an alkyl group which may have a substituent, an aryl group which may have a substituent, and a substituent.
  • the substituents may be the same or different.
  • halogen groups such as fluorine, chlorine and bromine, amino groups, hydroxyl groups and nitro groups.
  • an alkyl group, an aryl group, a cycloalkyl group, an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, and the like can be given.
  • alkyl group of the alkyl group which may have a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, Examples thereof include straight-chain or branched alkyl groups such as n-octyl group, stearyl group and 2-ethylhexyl group.
  • substituted alkyl group examples include trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl Group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2 , 4-dichlorobenzyl group and the like.
  • Examples of the “aryl group” of the aryl group which may have a substituent include a phenyl group, a naphthyl group, and an anthryl group.
  • Examples of the “substituted aryl group” include p-methylphenyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-amino Phenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthra A quinonyl group etc. are mentioned.
  • Examples of the “cycloalkyl group” of the cycloalkyl group which may have a substituent include a cyclopentyl group, a cyclohexyl group, an adamantyl group and the like.
  • Examples of the “cycloalkyl group having a substituent” include a 2,5-dimethylcyclopentyl group, a 4-tert-butylcyclohexyl group, and the like.
  • heterocyclic group examples include a pyridyl group, a pyrazyl group, a piperidino group, a pyranyl group, a morpholino group, and an acridinyl group.
  • heterocyclic group having a substituent examples include 3-methylpyridyl group, N-methylpiperidyl group, N-methylpyrrolyl group and the like.
  • alkoxyl group of the alkoxyl group which may have a substituent, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, 2 , 3-dimethyl-3-pentyloxy, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group and the like, and straight-chain or branched alkoxyl groups.
  • substituted alkoxyl group examples include trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2-ditrifluoro group.
  • substituted aryloxy group examples include p-methylphenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chloro group A phenoxy group etc. are mentioned.
  • a methylthio group an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a decylthio group, a dodecylthio group, and an octadecylthio group.
  • substituted alkylthio group examples include a methoxyethylthio group, an aminoethylthio group, a benzylaminoethylthio group, a methylcarbonylaminoethylthio group, and a phenylcarbonylaminoethylthio group.
  • Examples of the “arylthio group” of the arylthio group which may have a substituent include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and a 9-anthrylthio group.
  • Examples of the “substituted arylthio group” include a chlorophenylthio group, a trifluoromethylphenylthio group, a cyanophenylthio group, a nitrophenylthio group, a 2-aminophenylthio group, and a 2-hydroxyphenylthio group.
  • Y 1 to Y 4 include a halogen atom, a nitro group, an optionally substituted phthalimidomethyl group (C 6 H 4 (CO) 2 N—CH 2 —), and a substituent. And a suitable sulfamoyl group (H 2 NSO 2 —).
  • the phthalimidomethyl group having a substituent represents a structure in which a hydrogen atom in the phthalimidomethyl group is substituted with a substituent.
  • the sulfamoyl group having a substituent represents a structure in which a hydrogen atom in the sulfamoyl group is substituted with a substituent.
  • Preferred Y is a halogen atom and a sulfamoyl group.
  • a phthalocyanine compound in which m 1 to m 4 are 0 can also be suitably used.
  • the halogen atom include fluorine, chlorine, bromine and iodine.
  • the “substituent” of the phthalimidomethyl group which may have a substituent and the sulfamoyl group which may have a substituent has the same meaning as the substituents of X 1 to X 4 .
  • Z is represented by —OP ( ⁇ O) R 1 R 2 or —O—SiR 3 R 4 R 5 , wherein R 1 and R 2 each have a hydrogen atom, a hydroxyl group, and a substituent.
  • R 1 and R 2 each have a hydrogen atom, a hydroxyl group, and a substituent.
  • the alkyl group in R 1 and R 2 includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, and an n-octyl group.
  • straight-chain or branched alkyl groups such as stearyl group and 2-ethylhexyl group.
  • Examples of the substituent when the alkyl group is an alkyl group having a substituent include halogen atoms such as chlorine, fluorine and bromine, alkoxyl groups such as methoxy groups, aromatic groups such as phenyl groups and tolyl groups, nitro groups, and the like. Can be mentioned. Further, there may be a plurality of substituents. Examples of the alkyl group having a substituent include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2-ethoxyethyl group, and a 2-butoxyethyl group.
  • Examples of the aryl group in R 1 and R 2 include a phenyl group, a naphthyl group, and an anthryl group.
  • Examples of the substituent when the aryl group has a substituent include halogen atoms such as chlorine, fluorine and bromine, alkyl groups, alkoxyl groups, amino groups and nitro groups. Further, there may be a plurality of substituents.
  • Examples of the aryl group having a substituent include p-tolyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-dimethylamino group.
  • Examples include phenyl group, 2-methyl-4-chlorophenyl group, 4-methoxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group and the like.
  • Examples of the alkoxyl group in R 1 and R 2 include methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, neopentyloxy group, 2,3-dimethyl-3- Examples include a linear or branched alkoxyl group such as a pentyloxy group, an n-hexyloxy group, an n-octyloxy group, a stearyloxy group, and a 2-ethylhexyloxy group.
  • Examples include halogen atoms such as chlorine, fluorine and bromine, aryl groups such as alkoxyl groups, phenyl groups and tolyl groups, and nitro groups. Further, there may be a plurality of substituents.
  • Examples of the alkoxyl group having a substituent include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2-ditrifluoro group. Examples include methylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benzyloxy group and the like.
  • the aryloxy group in R 1 and R 2 there are a phenoxy group, a naphthaloxy group, an anthryloxy group, and the like.
  • the substituent is a halogen atom such as chlorine, fluorine, or bromine.
  • aryloxy group having a substituent examples include, for example, p-methylphenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group, 2-methyl-4-chloro There are phenoxy groups and the like.
  • R 1 and R 2 is preferably an aryl group that may have a substituent or an aryloxy group that may have a substituent. More preferably, R 1 and R 2 are both aryl groups or aryloxy groups. Further preferably, R 1 and R 2 are both a phenyl group or a phenoxy group.
  • R 3 , R 4 and R 5 are each independently a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, or an alkoxyl which may have a substituent. Or an aryloxy group which may have a substituent.
  • it is an alkyl group having 1 to 18 carbon atoms or an aromatic group having 4 or less rings. If the number of carbon atoms in the alkyl group exceeds 18 or the number of aromatic rings exceeds 4, the molecular weight increases and the extinction coefficient per unit weight decreases, so the pigment concentration in the coloring composition must be increased. It is not obtained and is not preferable.
  • the alkyl group in R 3 , R 4 , and R 5 may be linear, branched or cyclic, and has a functional group with a total number of heteroatoms of 3 or less. May be.
  • the aromatic ring may contain a hetero atom, and each aromatic ring may have a functional group in the range of 2 or less hetero atoms.
  • Z is more preferably —OP ( ⁇ O) R 1 R 2 .
  • phthalocyanine compound represented by the formula (1) As typical examples of the phthalocyanine compound represented by the formula (1), the following phthalocyanine compounds (a) to (v) may be mentioned, but the present invention is not limited thereto.
  • the phthalocyanine compound represented by the formula (1) may be the following phthalocyanines (A) to (D) having a specific crystal form.
  • Phthalocyanine (A): X-ray diffraction pattern represented by the formula (12) and CuK ⁇ ray shows a black angle 2 ⁇ ( ⁇ 0.2) 7.7 °, 8.4 °, 9.3 °, 12. 7 °, 15.0 °, 15.9 °, 16.7 °, 18.8 °, 20.1 °, 21.7 °, 23.1 °, 25.4 °, 26.5 °, 28.
  • Aluminum phthalocyanine having a peak at 2 ° Phthalocyanine (B): represented by the formula (12), and an X-ray diffraction pattern by CuK ⁇ ray shows a black angle 2 ⁇ ( ⁇ 0.2) 7.3 °, 8.6 ° , 14.4 °, 16.6 °, 18.2 °, 19.4 °, 23.2 °, 24.4 °, 26.7 °, aluminum phthalocyanine phthalocyanine (C) : The X-ray diffraction pattern represented by the formula (13) and CuK ⁇ ray has a black angle 2 ⁇ ( ⁇ 0.
  • the phthalocyanine (A) is obtained by reacting hydroxyaluminum phthalocyanine represented by the following formula (14) (hereinafter referred to as hydroxyaluminum phthalocyanine) with diphenylphosphinic acid in an organic solvent, and then removing the organic solvent. Can be manufactured. Moreover, phthalocyanine (C) can be manufactured by the method similar to phthalocyanine (A) using a diphenyl phosphate instead of said diphenylphosphinic acid.
  • hydroxyaluminum phthalocyanine one produced by hydrolyzing chloroaluminum phthalocyanine represented by the formula (15) may be used, or one obtained as a commercial product may be used.
  • diphenylphosphinic acid diphenylphosphinic acid obtained by hydrolyzing chlorodiphenylphosphine in dilute nitric acid may be used, or a commercially available product may be used.
  • diphenyl phosphate diphenyl phosphate obtained by hydrolyzing diphenyl chlorophosphate in dilute nitric acid or dilute sulfuric acid may be used, or a commercially available product may be used.
  • organic solvent examples include monohydric alcohol solvents such as methanol, ethanol, isopropanol, and t-butanol, ethylene glycol, propylene glycol, diethylene glycol, polyethylene glycol, thiodiglycol, dithiodiglycol, 2-methyl-1 , 3-propanediol, 1,2,6-hexanetriol, acetylene glycol derivatives, glycerol, polyhydric alcohol solvents such as trimethylolpropane, 1-methyl-2-pyrrolidinone, 1,3-dimethyl- 2-imidazolidinone, 2-pyrrolidinone, ⁇ -caprolactam, formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, N-methyl Amido solvents such as lopanamide, hexamethylphosphoric triamide, urea, tetramethylurea, etc., ethylene glycol mono
  • Monophenyl alcohol solvent such as methanol, ethanol, isopropyl alcohol, dimethyl sulfoxide, N, N-dimethylformamide, 1-methyl-2-pyrrolidinone, etc. because of good dissolution of diphenylphosphinic acid and diphenyl phosphate It is preferable to use the aprotic polar solvent. These organic solvents can be used alone or in admixture of two or more.
  • the organic solvent is compatible with the organic solvent used and washed with a low-boiling organic solvent, and then dried and removed.
  • hydroxyaluminum phthalocyanine has properties as a pigment
  • refining hydroxyaluminum phthalocyanine in advance it is easy to obtain fine phthalocyanine produced therefrom, so that when these are used as a coloring composition, high brightness and high contrast are easily obtained. There is an effect.
  • Examples of the method of miniaturization include methods known in the industry used for miniaturization of general colorants and pigments such as the acid pasting method and the solvent salt milling method.
  • the acid pasting method is a method of obtaining a fine colorant by adding a colorant to sulfuric acid and dissolving it, and then dropping a sulfuric acid solution into a large amount of water to cause precipitation.
  • the amount of water used for precipitation and the temperature, etc. it is possible to obtain colorant particles with a very fine primary particle size, a wide distribution range, and a sharp particle size distribution. Can do.
  • a mixture of a colorant, a water-soluble inorganic salt, and a water-soluble organic solvent is heated using a kneader such as a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor, or a sand mill.
  • a kneader such as a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor, or a sand mill.
  • the water-soluble inorganic salt serves as a crushing aid, and the colorant particles are crushed using the high hardness of the inorganic salt during salt milling.
  • the water-soluble inorganic salt sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price. From the viewpoint of both processing efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2000% by weight, and most preferably 300 to 1000% by weight, based on the total weight of the colorant (100% by weight).
  • the water-soluble organic solvent is not particularly limited as long as it functions to wet the colorant and the water-soluble inorganic salt and dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used.
  • the temperature rises during salt milling and the solvent easily evaporates, those having a high boiling point of 120 ° C. or higher are preferred from the viewpoint of safety.
  • These water-soluble organic solvents are preferably used in an amount of 5 to 1000% by weight, and most preferably 50 to 500% by weight, based on the total weight of the colorant (100% by weight).
  • a resin When the colorant is subjected to a salt milling treatment, a resin may be added as necessary.
  • the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used.
  • the resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the water-soluble organic solvent.
  • the amount of resin used is preferably in the range of 2 to 200% by weight, more preferably in the range of 5 to 200% by weight, based on the total weight of the colorant (100% by weight).
  • the phthalocyanine (B) can be produced by heat-treating the phthalocyanine (A) obtained by the above production method at 80 ° C. or higher.
  • a wet cake (paste) of phthalocyanine (A) is allowed to stand in a temperature-controlled room at 80 ° C. or higher; Or by stirring and heating in an organic solvent at 80 ° C. or higher.
  • the phthalocyanine (D) can be produced by heat-treating the phthalocyanine (C) obtained by the above production method at 135 ° C. or higher.
  • Examples of the heat treatment method at a temperature of 135 ° C. or higher include a method in which the dried phthalocyanine (C) is allowed to stand in a temperature-controlled room at 135 ° C. or higher or stirred and heated in an organic solvent at 135 ° C. or higher. be able to.
  • One embodiment of the coloring composition for a color filter may contain a phthalocyanine compound represented by the following formula (3) in addition to or instead of the phthalocyanine compound represented by the above formula (1).
  • X 5 to X 12 in the formula (3) have the same meanings as X 1 to X 4 in the formula (1).
  • Y 5 to Y 12 in the formula (3) have the same meanings as Y 1 to Y 4 in the formula (1).
  • N 5 to n 12 in the formula (3) are synonymous with n 1 to n 4 in the formula (1).
  • M 5 to m 12 in the formula (3) are synonymous with m 1 to m 4 in the formula (1).
  • R 6 to R 10 have the same meanings as R 1 and R 2 in formula (1). Among them, from the viewpoint of the viscosity and color characteristics of the dispersion, at least one of R 6 to R 7 and R 6 to R 9 and R 10 may have an aryl group or a substituent which may have a substituent. It is preferably a good aryloxy group. More preferably, R 6 to R 7 , R 6 to R 9 , and R 10 are all aryl groups or aryloxy groups.
  • R 6 to R 7 , R 6 to R 9 , and R 10 are all phenyl groups or phenoxy groups.
  • the phthalocyanine compound represented by the formula (3) may be used by replacing all or part of the phthalocyanine compound represented by the formula (1) with the phthalocyanine compound represented by the formula (3). It shall be possible.
  • One embodiment of the coloring composition for a color filter may further contain a yellow pigment within a range that does not impair the effects of the present invention in order to further adjust the chromaticity.
  • the yellow pigment is not particularly limited, and generally includes a yellow dye or a yellow pigment.
  • Yellow dyes include azo dyes, azo metal complex dyes, anthraquinone dyes, indigo dyes, thioindigo dyes, phthalocyanine dyes, diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, thiazine dyes, cationic dyes, cyanine dyes, nitro dyes, quinoline dyes , Naphthoquinone dyes and oxazine dyes.
  • yellow dyes include C.I. I. Acid Yellow 2, 3, 4, 5, 6, 7, 8, 9, 9: 1, 10, 11, 11: 1, 12, 13, 14, 15, 16, 17, 17: 1, 18, 20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40: 1, 41, 42, 42: 1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66, 67, 68, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 19 Etc.
  • C.I. Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44: 1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, 134 etc. are also mentioned.
  • C.I. I. Disperse Yellow 1, 2, 3, 5, 7, 8, 10, 11, 13, 13, 23, 27, 33, 34, 42, 45, 48, 51, 54, 56, 59, 60, 63, 64 67, 70, 77, 79, 82, 85, 88, 93, 99, 114, 118, 119, 122, 123, 124, 126, 163, 184, 184: 1, 202, 211, 229, 231, 232 233, 241, 245, 246, 247, 248, 249, 250, 251 and the like.
  • organic or inorganic pigments can be used alone or in admixture of two or more.
  • a pigment having high color developability and high heat resistance, particularly a pigment having high heat decomposition resistance is preferable, and an organic pigment is usually used.
  • the organic pigment commercially available ones can be used, and natural pigments and inorganic pigments can be used in combination according to the desired hue of the filter segment.
  • yellow organic pigment which can be used for the said coloring composition.
  • yellow pigments include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 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, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 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,
  • C.I. I. Pigment Yellow 138, 139, 150, and 185 are preferable. These yellow pigments can be used alone or in combination of two or more depending on the desired color characteristics.
  • the weight ratio of the yellow pigment / the phthalocyanine compound represented by the formula (1) is preferably in the range of 40/60 to 90/10. Within the above range, the brightness and color reproducibility are good.
  • Green pigment In one embodiment of the color filter coloring composition, a green pigment may be added for the purpose of adjusting the hue.
  • examples of the green pigment include C.I. I. And green pigments such as CI Pigment Green 7, 10, 36, 37, and 58.
  • the weight ratio of the green pigment / the phthalocyanine compound represented by the formula (1) is preferably in the range of 50/50 to 95/5. Within the above range, the brightness and color reproducibility are good.
  • the coloring composition for a color filter may contain a pigment having an acidic group amount of 100 to 600 ⁇ mol / g.
  • the amount of the acidic group is preferably a pigment of 150 to 600 ⁇ mol / g from the viewpoint of dispersibility and dispersion stability.
  • Such a pigment is not particularly limited as long as it has an acidic group amount of 100 to 600 ⁇ mol / g, but when used as a green coloring composition for a color filter, a green pigment or a yellow pigment is preferable.
  • the acidic group amount of a pigment is greatly influenced by the selection of the pigment type and the primary particle size of the pigment.
  • a pigment having a low acidity can be used by treating the surface with an acidic substance such as an acidic derivative to have a high surface amine adsorption amount.
  • a commercially available pigment whose surface has been acid-treated may be used.
  • the amount of acidic groups is defined by the amount of amine adsorbed when measured using n-hexylamine as the adsorbed amine substance in accordance with the method described in Color Material, 67 [9], 547-554 (1994). . Color material, 67 [9], 547-554 (1994), is incorporated herein in its entirety for reference.
  • pigment having an acidic group amount of 100 to 600 ⁇ mol / g examples include C.I. I. Pigment yellow 139, 150, C.I. I. Pigment green 58. More preferably, from the viewpoint of dispersibility, C.I. I. Pigment Green 58 is preferable.
  • the weight ratio of the pigment having an acidic group amount of 100 to 600 ⁇ mol / g to the total of the aluminum phthalocyanine pigments represented by formulas (1) and (3) is 5/95 or more. To preferred.
  • the colorant particles are refined by a salt milling process, etc. It can be preferably used.
  • the primary particle diameter of the colorant is preferably 5 nm or more, more preferably 10 nm or more, and still more preferably 20 nm or more in order to improve dispersibility in the colorant carrier.
  • 90 nm or less is preferable, 80 nm or less is more preferable, and 70 nm or less is more preferable.
  • it may be 5 to 90 nm, 10 to 70 nm, or 20 to 60 nm.
  • the miniaturization of the colorant is the same as the above-described miniaturization method.
  • Binder resin examples include a thermoplastic resin and a thermosetting resin.
  • a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region is preferable.
  • the weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 100,000, more preferably in the range of 8,000 to 50,000 in order to disperse the colorant preferably.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 50,000, and the value of Mw / Mn is preferably 10 or less.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) were determined by connecting four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation.
  • HCV-8120GPC gel permeation chromatography
  • the weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 to 50,000 in order to disperse the colorant preferably. Also good.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 40,000, and the value of Mw / Mn is preferably 10 or less.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are HLC-8220GPC (manufactured by Tosoh Corporation) as a device and TSK-GEL SUPER HZM-N is connected in series as a column. It is a molecular weight in terms of polystyrene measured using THF as a solvent.
  • a binder resin As a coloring composition for a color filter, from the viewpoint of dispersibility, developability, and heat resistance, a colorant adsorbing group and a carboxyl group that acts as an alkali-soluble group during development, a colorant carrier, and
  • the balance between the aliphatic group and aromatic group acting as an affinity group for the organic solvent is important for dispersibility, developability, and durability, and from the viewpoint of forming a fine pattern well, an acid value of 20 to 300 mgKOH / It is preferable to use g resin.
  • the binder resin can be used in an amount of 20 to 500% by weight based on the total weight of the colorant. When it is 20% by weight or more, the film formability and various resistances are sufficient, and when it is 500% by weight or less, the colorant concentration is moderate and the color characteristics are good.
  • thermoplastic resin examples include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin.
  • Polyester resin vinyl resin, alkyd resin, polystyrene resin, polyamide resin, rubber resin, cyclized rubber resin, celluloses, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resin.
  • an alkali-soluble vinyl resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer.
  • an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.
  • the resin is three-dimensionally crosslinked when exposed to active energy rays to form a coating film.
  • the colorant is fixed, heat resistance is improved, and fading (lightness reduction) due to heat of the colorant can be suppressed.
  • alkali-soluble vinyl resin copolymerized with an acidic group-containing ethylenically unsaturated monomer examples include resins having an acidic group such as a carboxyl group or a sulfone group.
  • Specific examples of the alkali-soluble vinyl resin include an acrylic resin having an acidic group, an ⁇ -olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, Or an isobutylene / (anhydrous) maleic acid copolymer etc. are mentioned.
  • At least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.
  • Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, aldehyde groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc.
  • a resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used.
  • polymers containing acid anhydrides such as styrene-maleic anhydride copolymer and ⁇ -olefin-maleic anhydride copolymer are half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate.
  • a modified version is also used.
  • thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferable as the photosensitive coloring composition for color filters.
  • Examples of the monomer constituting the thermoplastic resin include the following. For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) Acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypol
  • a structural unit derived from N-substituted maleimide and cyclohexylmaleimide, methylmaleimide, ethylmaleimide, and 1,2-bismaleimideethane are particularly preferable from the viewpoint of heat resistance, and cyclohexylmaleimide is particularly preferable.
  • thermoplastic resin is preferably added in the range of 20 to 500 parts by weight with respect to 100 parts by weight of the colorant. If it is 20 parts by weight or more, the developability during alkali development is good, and if it is 500 parts by weight or less, the colorant concentration is appropriate and the color characteristics are good.
  • thermosetting resin examples include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.
  • the color filter coloring composition of the present invention preferably contains a thermosetting resin in terms of heat resistance.
  • a thermosetting resin in terms of heat resistance.
  • epoxy resins and melamine resins can be more suitably used, and melamine resins are particularly preferable, and melamine compounds having a methylolimino group or condensates thereof are more preferable.
  • thermosetting resin is preferably added in the range of 5 to 60 parts by weight with respect to 100 parts by weight of the colorant. When it is 10 parts by weight or more, the heat resistance and light resistance are good, and when it is 60 parts by weight or less, the developability during alkali development is good.
  • Vinyl resin [B1] One embodiment of the coloring composition for a color filter is a vinyl resin in which an ethylenically unsaturated double bond is introduced using an ethylenically unsaturated monomer having an epoxy group as a binder resin, and has the following constitution A vinyl resin [B1] containing units (b1) and (b2) may be contained.
  • R 4 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a benzene ring.
  • each structural unit is the weight% of the precursor that brings each structural unit to the vinyl resin [B1].
  • the structural unit (b1) has a carboxyl group and functions as an alkali-soluble site during development. Based on the weight of all the structural units of the vinyl resin [B1], the structural unit (b1) is preferably 2 to 60% by weight from the viewpoint of developability. If it is 2% by weight or more, the removability of the unexposed part by the alkaline developer is sufficient, and if it is 60% by weight or less, the dissolution rate in the alkali developer is moderate and the exposed part is not dissolved.
  • the structural unit (b1) corresponds to a carboxyl group that is not used for an addition reaction with an epoxy group by a method using a precursor of the structural unit (b1) having a carboxyl group and a method (i-1) described later.
  • the unit may be the structural unit (b1) in the vinyl resin.
  • Examples of the precursor of the structural unit (b1) having a carboxyl group include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, and ⁇ -chloroacrylic acid, and unsaturated dicarboxylic acids such as maleic acid and fumaric acid. And compounds containing a carboxyl group such as an acid and having an ethylenically unsaturated double bond. Moreover, what half-esterified the anhydride of unsaturated dicarboxylic acid, such as maleic anhydride, with the (meth) acrylic compound which has hydroxyl groups, such as hydroxyalkyl (meth) acrylate, can also be used. Among these, (meth) acrylic acid is more preferable, and methacrylic acid is most preferable from the viewpoint of polymerizability (ease of control of molecular weight and the like). These can be used alone or in combination of two or more.
  • the structural unit (b2) has a cyclic structure with an aromatic ring group represented by the formulas (5) and (6), and functions as an affinity site for a pigment or a pigment composition comprising a pigment and a dispersant.
  • the structural unit (b2) is preferably 2 to 80% by weight from the viewpoints of developability, dispersion stability, and chemical resistance. When it is 2% by weight or more, developability, dispersion stability, and chemical resistance are good. On the other hand, when it is 80% by weight or less, the dissolution rate in an alkali developer becomes appropriate, the development time is short, and the productivity is good.
  • styrene As the precursor of the structural unit (b2), styrene, ⁇ -methylstyrene, divinylbenzene, indene, acetylnaphthene, benzyl acrylate, benzyl methacrylate, bisphenol A diglycidyl ether di (meth) acrylate, (meth) of methylolated melamine Examples thereof include monomers / oligomers such as acrylic acid esters, and ethylenically unsaturated monomers represented by the formula (7).
  • R 6 is a hydrogen atom or a methyl group
  • R 7 is an alkylene group having 2 or 3 carbon atoms
  • R 8 is a carbon number optionally having a benzene ring. 1 to 20 alkyl groups
  • n is an integer of 1 to 15.
  • the alkyl group of R 8 has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms.
  • the alkyl group includes not only a linear alkyl group but also a branched alkyl group and an alkyl group having a benzene ring as a substituent.
  • the carbon number of the alkyl group of R 8 is 1 to 10
  • the alkyl group becomes an obstacle and the penetration of the ITO etching solution, the metal etching solution, etc. is suppressed and the chemical resistance is improved, but when the carbon number exceeds 10, the alkyl group The steric hindrance effect is increased, and the adhesion to the base material tends to be prevented.
  • the alkyl group having a benzene ring represented by R 8 include a benzyl group and a 2-phenyl (iso) propyl group.
  • n is preferably an integer of 1 to 15.
  • n is 15 or less, the hydrophilicity is moderate and the effect of solvation is increased, and the viscosity of the vinyl resin [B1] is moderate.
  • the viscosity of the photosensitive composition using the resin is also moderate, and the desired flow Sex is obtained.
  • n is particularly preferably 1 to 4.
  • styrene As the precursor of the structural unit (b2), styrene, ⁇ -methylstyrene, benzyl acrylate, benzyl methacrylate, or a compound represented by the formula (7) from the viewpoint of copolymerization with other precursors and chemical resistance.
  • the ethylenically unsaturated monomers shown are preferred. These are particularly preferable because a benzene ring can be introduced into the side chain of the vinyl resin [B1]. By introducing a benzene ring into the side chain of the vinyl resin, the side chain benzene ring is oriented to the pigment, so that the resin adsorption to the pigment is promoted and the pigment aggregation is also suppressed.
  • benzyl acrylate and / or benzyl methacrylate are most preferred from the viewpoints of developability and dispersion stability.
  • the vinyl resin [B1] may have structural units other than the structural unit (b1) and the structural unit (b2) as other structural units.
  • the main function of other structural units is to provide developability, a small structure is formed with respect to the relatively large ring structure of the side chain of the structural unit (b2) having a chemical resistance function. It is preferable to take. Thus, it is considered that developability can be imparted while maintaining the properties of the structural unit (b2) having a large side chain having chemical resistance.
  • the vinyl resin [B1] further contains a structural unit (b3) having a cyclic structure with an aliphatic cyclic group represented by the formulas (8) and (9).
  • the structural unit (b3) has a cyclic structure with an aliphatic cyclic group represented by the formula (8) and the formula (9), and serves as an affinity site for a pigment or a pigment composition comprising a pigment and a dispersant, and the like. Functions as a hydrophobic site for the alkaline developer.
  • Examples of other structural unit precursors include: Methyl (meth) methacrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (Meth) acrylate, pentyl (meth) acrylate, isopentyl acrylate, neopentyl (meth) acrylate, t-pentyl (meth) acrylate, 1-methylbutyl (meth) acrylate, hexyl (meth) acrylate, hepta (meth) acrylate, octyl (Meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acryl
  • Examples of other ethylenically unsaturated monomers include: (Meth) acrylates having a heterocyclic substituent such as tetrahydrofurfuryl (meth) acrylate or 3-methyloxetanyl (meth) acrylate; Alkoxypolyalkylene glycol (meth) acrylates such as methoxypolypropylene glycol (meth) acrylate or ethoxypolyethylene glycol (meth) acrylate; or (Meth) acrylamide (Note that “(meth) acrylamide” indicates acrylamide and / or methacrylamide; the same shall apply hereinafter), N, N-dimethyl (meth) acrylamide, N, N And (meth) acrylamides such as diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, and acryloylmorpholine.
  • a heterocyclic substituent such as t
  • a monomer other than the acrylic monomer for example, Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether; or Examples include vinyl acetate, and fatty acid vinyls such as vinyl propionate.
  • the monomer other than the acrylic monomer can be used in combination with the acrylic monomer.
  • the structural unit (b3) has 2 to 60% by weight based on the weight of all the structural units of the vinyl resin [B1] (100% by weight) from the viewpoint of developing property, dispersion stability, and chemical resistance. Is preferred.
  • the content is 2% by weight or more, the affinity part for the pigment composition composed of the pigment or the pigment and the dispersing agent is sufficient, and a high-quality color filter can be obtained, or the storage stability of the coloring composition for the color filter is improved. It is preferable because it becomes good. Further, it is favorable without causing a problem of pattern peeling or chipping in the pixel portion.
  • the amount of 60% by weight or less is preferable because the dissolution rate in an alkali developer is high, the development time is short, and the productivity of the color filter is improved.
  • Examples of the precursor of the structural unit (b3) include an ethylenically unsaturated monomer represented by the formula (10), an ethylenically unsaturated monomer represented by the formula (11), and the like.
  • R 9 is a hydrogen atom or a methyl group
  • R 10 is an alkylene group having 2 or 3 carbon atoms
  • m is an integer of 1 to 15. .
  • the vinyl resin [B1] includes a structural unit (b4) having an ethylenically unsaturated double bond in which an ethylenically unsaturated double bond is introduced using an ethylenically unsaturated monomer having an epoxy group. It is the vinyl resin which has.
  • the vinyl resin [B1] has a double bond group and functions as a site that improves the pattern shape.
  • the structural unit (b4) having an ethylenically unsaturated double bond is 2 to 60% by weight from the viewpoint of the pattern shape based on the weight (100% by weight) of all the structural units of the vinyl resin [B1]. preferable.
  • an ethylenically unsaturated double bond using an ethylenically unsaturated monomer having an epoxy group an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having an epoxy group can be used. Examples thereof include a method in which an ethylenically unsaturated double bond is introduced using a monomer to form a photosensitive resin, and a method (i1) or a method (i2) shown below is exemplified.
  • Method (i1) Examples of a method for introducing an ethylenically unsaturated double bond using an ethylenically unsaturated monomer having an epoxy group include an ethylenically unsaturated monomer having an epoxy group and one or more other types of ethylene.
  • a carboxyl group of an unsaturated monobasic acid having an ethylenically unsaturated double bond is added to the side chain epoxy group of the copolymer obtained by copolymerizing with the polymerizable unsaturated monomer, There is a method (i1) in which a polybasic acid anhydride is reacted with the generated hydroxyl group, an ethylenically unsaturated double bond is introduced to give the function of a photosensitive resin, and a carboxyl group having an alkali-soluble function is introduced.
  • a copolymer (i1-1) is obtained by reacting a precursor of the structural unit (b2) with an ethylenically unsaturated monomer having an epoxy group, and then the copolymer (i1) -1) and an unsaturated monobasic acid to obtain a copolymer (i1-2), and further obtained by reacting the obtained copolymer (i1-2) with a polybasic acid anhydride.
  • the resin used is preferable because the pattern shape is good.
  • the structural unit (b1) of the vinyl resin [B1] in this specification since the carboxyl group of the unsaturated monobasic acid used in this method (i1) forms an ester bond after the addition reaction to the epoxy group, the structural unit (b1) of the vinyl resin [B1] in this specification Since the polybasic acid anhydride forms a carboxyl group after reaction with a hydroxyl group, it corresponds to the structural unit (b1) of the vinyl resin [B1] in this specification.
  • Method (i2) Alternatively, a part of the side chain carboxyl group of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a carboxyl group and one or more other ethylenically unsaturated monomers. And the method (i2) of introducing an ethylenically unsaturated double bond and a carboxyl group by addition reaction of an ethylenically unsaturated monomer having an epoxy group.
  • the precursor of the structural unit (b1) and the precursor of the structural unit (b2) are reacted to obtain a copolymer (i2-1), and then the copolymer (i2-1) obtained
  • a resin obtained by reacting an ethylenically unsaturated monomer having an epoxy group is preferable because of excellent heat resistance.
  • Examples of the ethylenically unsaturated monomer having an epoxy group include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 2-glycidoxyethyl (meth) acrylate, and 3,4-epoxybutyl (meth) acrylate. And 3,4-epoxycyclohexyl (meth) acrylate, and these may be used alone or in combination of two or more.
  • Glycidyl (meth) acrylate is preferred from the viewpoint of reactivity with the unsaturated monobasic acid in the next step and from the viewpoint of substrate adhesion.
  • Unsaturated monobasic acids include (meth) acrylic acid, crotonic acid, o-, m-, P-vinylbenzoic acid, ⁇ -haloalkyl of (meth) acrylic acid, alkoxyl, halogen, nitro, cyano substituted products, etc.
  • Monocarboxylic acid etc. are mentioned, These may be used independently or may use 2 or more types together. Of these, (meth) acrylic acid is preferred.
  • polybasic acid anhydrides examples include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, and the like. These may be used alone or in combination of two or more. It doesn't matter. If necessary, use a tricarboxylic anhydride such as trimellitic anhydride or a tetracarboxylic dianhydride such as pyromellitic dianhydride to increase the number of carboxyl groups. The group can also be hydrolyzed. Further, when etrahydrophthalic anhydride or maleic anhydride having an ethylenically unsaturated double bond is used as the polybasic acid anhydride, the ethylenically unsaturated double bonds can be further increased.
  • the number average molecular weight (Mn) of the vinyl resin [B1] has already been described as the number average molecular weight of the binder resin, but is more preferably in the range of 5,000 to 50,000.
  • the vinyl resin [B1] is preferably used in an amount of 20 to 500 parts by weight with respect to 100 parts by weight of the colorant. When it is 20 parts by weight or more, the film formability and various resistances are good, and when it is 500 parts by weight or less, the concentration of the colorant becomes appropriate and the color characteristics are good.
  • the coloring composition for a color filter may contain a dispersion aid.
  • a dispersion aid such as a pigment derivative, a resin-type dispersant, or a surfactant can be appropriately used. Since the dispersion aid is excellent in dispersion of the colorant and has a large effect of preventing reaggregation of the colorant after dispersion, a coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid is , Lightness and viscosity stability are improved.
  • a coloring composition obtained by dispersing a colorant in a colorant carrier using a dispersion aid is used, a color filter having a high spectral transmittance can be obtained.
  • dye derivative examples include compounds obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group which may have a substituent into an organic pigment, anthraquinone, acridone, or triazine.
  • a pigment derivative having a copper phthalocyanine structure as a base skeleton is preferable because the dispersibility of the colorant is improved and the heat resistance and light resistance of the colored composition are improved.
  • the pigment derivative having a copper phthalocyanine structure as a base skeleton is preferably added in an amount of 10 to 40 parts by weight with respect to 100 parts by weight of the aluminum phthalocyanine pigment in the colorant.
  • the blending amount of the pigment derivative is preferably 0.5% by weight or more, more preferably 1% by weight or more, more preferably from the viewpoint of improving the dispersibility of the colorant, based on the total amount of the colorant (100% by weight). It is 3% by weight or more, particularly preferably 5% by weight or more. Further, from the viewpoint of heat resistance and light resistance, the total amount of the colorant is based on (100% by weight), preferably 40% by weight or less, more preferably 35% by weight or less, more preferably 30% by weight or less, particularly preferably. 25% by weight or less.
  • Resin type dispersants have a colorant affinity part that has the property of adsorbing to the colorant and a part that is compatible with the colorant carrier, and adsorb to the colorant to stabilize dispersion in the colorant carrier. It works to do.
  • resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts.
  • Oil-soluble dispersants such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc.
  • Resin water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide adduct, phosphoric acid ester, and the like. These can be used alone or in admixture of two or more, but are not necessarily limited thereto.
  • a polymer dispersant having a basic functional group is preferable because the viscosity of the dispersion is lowered and a high contrast is exhibited with a small addition amount, and a nitrogen atom-containing graft copolymer or side chain is preferable.
  • Nitrogen atom-containing acrylic block copolymers and urethane polymer dispersants having functional groups including tertiary amino groups, quaternary ammonium bases, nitrogen-containing heterocycles and the like are preferred.
  • the resin-type dispersant is preferably used in an amount of about 5 to 200% by weight relative to the total amount of the pigment, and more preferably about 10 to 100% by weight from the viewpoint of film formability.
  • the content of the resin-type dispersant is preferably 0.1 to 55 parts by weight, more preferably 0.1 to 45 parts by weight with respect to 100 parts by weight of the colorant. Also good.
  • the content of the resin-type dispersant is 0.1 parts by weight or more, the added effect is sufficiently obtained, and when the content is 55 parts by weight or less, the dispersion is very good.
  • resin-type dispersants include Dsperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 167 manufactured by Big Chemie Japan.
  • Base resin type dispersant a basic resin-type dispersant having an amine value of 10 to 300 mgKOH / g is preferably included. More preferably, it is 50 to 300 mgKOH / g.
  • a basic resin type dispersant having an amine value within this range is used, the pigment is sufficiently adsorbed by the adsorption or reaction with respect to the acidic component in the pigment carrier, whereby the dispersion becomes good and the dispersion stability is excellent.
  • a dispersant By using a dispersant, a color filter coloring composition having excellent dispersibility and dispersion stability can be obtained.
  • the number average molecular weight of the basic resin dispersant is usually preferably 500 to 50000, more preferably 3000 to 30000.
  • the compatibility effect with the pigment carrier is good, and the compatibility effect with the pigment carrier and the solvent when a solvent is used. Is good, the aggregation of the pigment is prevented and the viscosity of the dispersion does not increase too much.
  • the number average molecular weight is 50000 or less, the amount of resin necessary for dispersion is sufficient, and the pigment concentration in the coating film does not decrease.
  • the basic resin type dispersant having an amine value of 10 to 300 mgKOH / g various types of resin types such as vinyl type, urethane type, polyester type, polyether type, and polyamide type can be used.
  • a vinyl monomer copolymer type that is easy and excellent in various resistances is preferable. Specifically, N, N-disubstituted amino group-containing vinyl monomer units, alkyl (meth) acrylate monomer units, and other vinyl monomers Copolymer resins with units are preferred.
  • N, N-disubstituted amino group-containing vinyl monomer units examples include N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, Examples thereof include N, N-diethylaminopropyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylamide, and N, N-diethylaminoethyl (meth) acrylamide, but are not necessarily limited thereto. These monomer units are adsorbed to the pigment as basic group-containing monomer units.
  • Alkyl (meth) acrylate monomer units include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, It is obtained by reacting an unsaturated monocarboxylic acid such as 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, or lauryl (meth) acrylate with an alkyl alcohol having 1 to 18 carbon atoms (meta ) Acrylic esters and the like, but are not necessarily limited thereto. These monomer units act as pigment carrier affinity groups.
  • vinyl monomer units include nitro group-containing vinyl monomers such as (meth) acrylonitrile, vinyl aromatic monomers such as styrene, ⁇ -methylstyrene, or benzyl (meth) acrylate, 2-hydroxyethyl ( Hydroxyl group-containing vinyl monomers such as (meth) acrylate, hydroxypropyl (meth) acrylate, or polyethylene glycol (meth) acrylate, (meth) acrylamide, N, N-dimethylacrylamide, N-isopropylacrylamide, diacetone acrylamide, etc.
  • nitro group-containing vinyl monomers such as (meth) acrylonitrile, vinyl aromatic monomers such as styrene, ⁇ -methylstyrene, or benzyl (meth) acrylate, 2-hydroxyethyl ( Hydroxyl group-containing vinyl monomers such as (meth) acrylate, hydroxypropyl (meth) acrylate, or polyethylene glycol (me
  • vinyl monomers such as N-methylol (meth) acrylamide or dimethylol (meth) acrylamide, N-methoxymethyl (meth) acrylamide, or N-butoxy Alkoxymethyl group-containing vinyl monomers such as til (meth) acrylamide, olefins such as ethylene, propylene or isoprene, dienes such as chloroprene or butadiene, methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, Examples thereof include vinyl ethers such as n-butyl vinyl ether or isobutyl vinyl ether, vinyl acetates, and fatty acid vinyls such as vinyl propionate, and the like, which are appropriately used according to the purpose, but are not necessarily limited thereto.
  • Polymers having primary amino group-containing monomer units such as allylamine, or polyethyleneimine, polyethylene polyamine, polyxylylene poly (hydroxypropylene) polyamine, or poly (aminomethylated) epoxy resin, polyester resin, acrylic resin Alternatively, a comb-shaped basic resin dispersant modified with a polyether resin or the like can also be used.
  • DISPERBYK 161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185 2000, 2050, manufactured by Big Chemie Japan, 2150, 2163, 2164, or BYK-LPN6919, 21324, 21407, Nippon Lubrizol SOLPERSE 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100, EFKA4300, 4330, 4046, 4060, 40 from Ciba Japan 0, and the like.
  • the content of the basic resin type dispersant is preferably 5 to 100 parts by weight, more preferably 10 to 80 parts by weight with respect to 100 parts by weight of the colorant from the viewpoint of dispersibility and film-forming property.
  • Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate
  • Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester, Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene
  • Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostea
  • the total amount of the resin-type dispersant and the surfactant is preferably 0.1 to 55% by weight, more preferably 0.1 to 45% by weight, based on the total amount of the colorant (100% by weight). is there.
  • the blending amount of the resin-type dispersant and the surfactant is 0.1% by weight or more, the added effect is sufficiently obtained, and when the blending amount is 55% by weight or less, the dispersion is good.
  • Organic solvent can easily form a filter segment by sufficiently dispersing and infiltrating the colorant in the colorant carrier and applying it on a substrate such as a glass substrate to a dry film thickness of 0.2 to 5 ⁇ m.
  • organic solvent examples include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl 1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m -Diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N Dimethylformamide, n
  • glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, benzyl alcohol, etc.
  • ketones such as aromatic alcohols and cyclohexanone.
  • ethyl lactate propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, etc.
  • alcohols such as glycol acetates, benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone.
  • Organic solvents can be used alone or in combination of two or more.
  • the organic solvent can adjust the coloring composition to an appropriate viscosity and form a filter segment having a desired uniform film thickness. Therefore, 500 to 4000% by weight based on the total weight of the coloring agent (100% by weight). It is preferable to use it in the quantity.
  • the color filter coloring composition may contain a photopolymerizable monomer.
  • the photopolymerizable monomer includes a monomer or oligomer that is cured by ultraviolet rays or heat to produce a transparent resin, and these can be used alone or in admixture of two or more.
  • the blending amount of the photopolymerizable monomer is preferably 5 to 400% by weight based on the total weight of the colorant (100% by weight), and 10 to 300% by weight from the viewpoint of photocurability and developability. It is more preferable that
  • Monomers and oligomers that are cured by ultraviolet rays or heat to produce transparent resins include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate , Cyclohexyl (meth) acrylate, ⁇ -carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglyme Diether ether di (meth) acrylate
  • the photopolymerizable monomer may contain a polyfunctional monomer having an acid group.
  • Such monomers include, for example, esterified products of poly (meth) acrylates containing free hydroxyl groups of polyhydric alcohol and (meth) acrylic acid and dicarboxylic acids; polyhydric carboxylic acids and monohydroxyalkyl (meth) Examples include esterified products with acrylates.
  • monomethyl oligoacrylates or monohydroxy oligomethacrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol pentamethacrylate.
  • Monoesterified products containing free carboxyl groups with dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, terephthalic acid; propane-1,2,3-tricarboxylic acid (tricarballylic acid), butane-1,2,4 -Tricarboxylic acids such as tricarboxylic acid, benzene-1,2,3-tricarboxylic acid, benzene-1,3,4-tricarboxylic acid, benzene-1,3,5-tricarboxylic acid And a free carboxyl group-containing oligoester product of monohydroxy monoacrylate or monohydroxy monomethacrylate such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, etc. be able to.
  • These polyfunctional monomers can be used singly or in combination of two or more at any ratio as required.
  • the compound represented by following formula (16) can also be used preferably.
  • R 4 is a hydrogen atom or a methyl group
  • R 5 is a hydrocarbon group having 1 to 12 carbon atoms
  • X is an (m + n) -valent carbon number 3 to 60 M represents an integer of 2 to 18, and n represents an integer of 1 to 3.
  • M represents an integer of 2 to 18, and n represents an integer of 1 to 3.
  • the compound represented by Formula (16) can be easily obtained by the following method, for example.
  • (1) A method in which a compound giving an organic group represented by X is esterified with acrylic acid to be acrylated, and then a mercapto compound is added to the obtained compound.
  • (2) After modifying the compound giving an organic group represented by X with a polyisocyanate compound, the resulting compound is acrylated with an acrylate compound having a hydroxyl group, and then a mercapto compound is added to the obtained compound.
  • Method A method in which a compound giving an organic group represented by X is esterified with acrylic acid to be acrylated, then modified with a polyisocyanate compound, and a mercapto compound is added to the obtained compound.
  • Examples of the compound giving an organic group represented by X include pentaerythritol, pentaerythritol modified caprolactone, pentaerythritol modified polyisocyanate, dipentaerythritol, dipentaerythritol modified caprolactone, and dipentaerythritol polyisocyanate. Denatured products can be mentioned.
  • Examples of the mercapto compound include mercaptoacetic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, o-mercaptobenzoic acid, 2-mercaptonicotinic acid, mercaptosuccinic acid and the like.
  • the content of the polyfunctional monomer having an acid group is preferably 5 to 500 parts by weight and more preferably 20 to 300 parts by weight with respect to 100 parts by weight of the binder resin.
  • the amount is 5 parts by weight or more, the pixel strength or the smoothness of the pixel surface becomes better, and when the amount is 500 parts by weight or less, the alkali developability is excellent. This is preferable because there is no dirt or film residue.
  • the content of the polyfunctional monomer having an acid group is based on the total amount of the photopolymerizable monomer (100% by weight). Is preferably 10% by weight or more, more preferably 50% by weight or more.
  • the content of the polyfunctional monomer (C1) having an acid group is 10% by weight or more, the developability and the image line-forming property are good, and the coloring composition on the non-pixel portion on the substrate after development There is no residue (development residue) or pattern missing and / or peeling of the pixel portion, and an excellent filter segment can be obtained.
  • the photosensitive coloring composition for color filters may contain a photopolymerization initiator.
  • a photopolymerization initiator When the composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, it can be prepared in the form of a solvent development type or alkali development type colored resist material by adding a photopolymerization initiator or the like.
  • the blending amount when using the photopolymerization initiator is preferably 2 to 200% by weight based on the total amount of the colorant, and 3 to 150 parts by weight from the viewpoint of photocurability and developability. More preferred is 5 to 150% by weight.
  • photopolymerization initiator examples include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1
  • Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as benzyld
  • an acetophenone compound or an oxime ester compound as a photopolymerization initiator in order to produce a color filter with good pattern shape and linearity.
  • An oxime ester-based compound absorbs ultraviolet rays to cleave the N—O bond of the oxime to generate an iminyl radical and a benzoyloxy radical. Since these radicals are further decomposed to generate radicals with high activity, a pattern can be formed with a small exposure amount.
  • oxime ester photoinitiators etanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (0-acetyloxime), 1,2- Octadione-1- [4- (phenylthio)-, 2- (O-benzoyloxime)] is preferred.
  • An acetophenone compound is cleaved to generate a radical having an amino group that becomes an active hydrogen donor, so that it is possible to reduce the influence of oxygen inhibition, which is a problem in UV curing, and to cure the surface of the coating film. .
  • acetophenone compounds include ⁇ -aminoalkyl acetophenone compounds such as 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino- 1- (4-morpholinophenyl) -butan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1- Butanone is preferred.
  • ⁇ -aminoalkyl acetophenone compounds such as 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino- 1- (4-morpholinophenyl) -butan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) pheny
  • photopolymerization initiators can be used alone or in combination of two or more at any ratio as required.
  • One Embodiment of the coloring composition for color filters may contain a sensitizer.
  • Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, te
  • Two or more sensitizers may be used at an arbitrary ratio as required.
  • the blending amount when using the sensitizer is preferably 3 to 60% by weight, based on the total weight (100% by weight) of the photopolymerization initiator contained in the colored composition, From the viewpoint of developability, it is more preferably 5 to 50% by weight.
  • One Embodiment of the photosensitive coloring composition for color filters may contain antioxidant.
  • a phthalocyanine dye represented by formula (1) and an antioxidant By including a phthalocyanine dye represented by formula (1) and an antioxidant, a color filter having a high transmittance of the coating film can be formed.
  • the antioxidant is used to prevent the photopolymerization initiator and thermosetting compound contained in the photosensitive coloring composition for the color filter from oxidizing and yellowing due to the thermal process during thermal curing or ITO annealing.
  • the transmittance can be increased. Therefore, by including an antioxidant, yellowing due to oxidation during the heating step can be prevented, and a high coating film transmittance can be obtained.
  • the “antioxidant” may be a compound having an ultraviolet absorption function, a radical scavenging function, or a peroxide decomposition function.
  • Specific examples of the antioxidant include hindered phenols, hindered amines, phosphoruss, sulfurs, benzotriazoles, benzophenones, hydroxylamines, salicylates, and triazines.
  • An ultraviolet absorber, antioxidant, etc. can be used.
  • a hindered phenol antioxidant a hindered amine antioxidant, a phosphorus antioxidant, or a sulfur antioxidant is preferable from the viewpoint of achieving both transmittance and sensitivity of the coating film.
  • Agents More preferably, they are hindered phenolic antioxidants, hindered amine antioxidants, or phosphorus antioxidants.
  • hindered phenol antioxidants examples include 2,4-bis [(laurylthio) methyl] -o-cresol, 1,3,5-tris (3,5-di-t-butyl-4-hydroxybenzyl), 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di -T-butylanilino) -1,3,5-triazine, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 2,6-di-t-butyl-4- Nonylphenol, 2,2'-isobutylidene-bis- (4,6-dimethyl-phenol), 4,4'-butylidene-bis- (2-tert-butyl-5-methylphenol), 2,2'- O-bis- (6-t
  • hindered amine antioxidants include bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (N-methyl-2,2,6,6-tetramethyl-4-piperidyl) sebacate, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) -1,6-hexamethylenediamine, 2-methyl-2- (2,2,6,6-tetramethyl-4 -Piperidyl) amino-N- (2,2,6,6-tetramethyl-4-piperidyl) propionamide, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) (1,2,3,3) 4-butanetetracarboxylate, poly [ ⁇ 6- (1,1,3,3-tetramethylbutyl) imino-1,3,5-triazine-2,4-diyl ⁇ ⁇ (2,2,6,6 -Tetramethyl-4-piperi L) imino ⁇ hexamethyl ⁇ (2,2,
  • hindered amine antioxidants include Sanol LS-770, Sanol LS-765, Sanol LS-622LD, Kimasorp 944 (Sankyo Co., Ltd.), CYASORB® UV-3346 (San Chemical Co., Ltd.), Knock rack 224, knock rack CD, Uvasil 299-299LM (above, Ouchi Shinsei Chemical Industry Co., Ltd.), MARK LA-63, MARKLA-68 (above, Asahi Denka Kogyo Co., Ltd.), TINUVIN 144, TINUVIN 312 (above, BASF ⁇ Made by Japan).
  • Phosphorous antioxidants include tris (isodecyl) phosphite, tris (tridecyl) phosphite, phenyl isooctyl phosphite, phenyl isodecyl phosphite, phenyl di (tridecyl) phosphite, diphenyl isooctyl phosphite, diphenyl isodecyl Phosphite, diphenyltridecyl phosphite, triphenyl phosphite, tris (nonylphenyl) phosphite, 4,4 ′ isopropylidenediphenol phosphite, trisnonylphenyl phosphite, trisdinonylphenyl phosphite, tris (2 , 4-di-t-butylphenyl) phosphite, tris (bi
  • phosphorus antioxidants include IRGAFOS168, IRGAFOS12, IRGAFOS38, IRGAFOSEPQ (above, manufactured by BASF Japan Ltd.), Sumizer Z-16 (manufactured by Sumitomo Chemical Co., Ltd.), ADK STAB PEP-4C, ADK STAB PEP-8F, ADK STAB PEP-8, ADK STAB PEP-45, ADK STAB PEP-11C, ADK STAB PEP-24G, ADK STAB PEP-36, ADK STAB HP-10, ADK STAB P, ADK STAB C, ADK STAB QL, ADK STAB 135A, ADK STAB 1178, ADK STAB 1500, ADK STAB 1500 ADK STAB 3010, ADK STAB 522A, ADK STAB TPP (above, manufactured by Asahi Denka Kogyo Co., Ltd.), GSY-202 (above, API Chromatography manufactured poration), SANKOHCA (Sanko Co., Ltd.
  • antioxidants 2,2-thio-diethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2,4-bis [(octylthio) methyl]- o-cresol, 2,4-bis [(laurylthio) methyl] -o-cresol, and the like.
  • Other examples include oligomer type and polymer type compounds having a thioether structure.
  • sulfur-based antioxidants include IRGANOXPS800FD, IRGANOXPS802FD (above, manufactured by BASF Japan Ltd.), Adekastab AO-503, Adekastab AO-412S (above, made by Asahi Denka Kogyo Co., Ltd.), Sumizer ZPL-R, Sumizer TPM, TPM Sumitizer TP-D, Sumitizer TL, Sumitizer MB (above, manufactured by Sumitomo Chemical Co., Ltd.), DLTP “Yoshitomi”, DSTP “Yoshitomi”, DMTP “Yoshitomi”, and DTTP “Yoshitomi” (above, manufactured by API Corporation).
  • benzotriazole antioxidant examples include oligomer type and polymer type compounds having a benzotriazole structure.
  • benzotriazole antioxidants include Tomisorp 600 (manufactured by Yoshitomi Fine Chemical), TINUVIN 326, TINUVIN 327, TINUVIN P, TINUVIN 328 (above, manufactured by BASF Japan), VIOSORB 583, and VIOSORB 590 (manufactured by Kyodo Yakuhin).
  • benzophenone antioxidant examples include oligomer type and polymer type compounds having a benzophenone structure.
  • benzophenone antioxidant examples include 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4 -Octadecyloxybenzophenone, 2,2'dihydroxy-4-methoxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4 -Methoxy-5 sulfobenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, 2-hydroxy-4-chlorobenzophenone, LA-51 (manufactured by Asahi Denka Kogyo Co., Ltd.) and the like.
  • Other examples include oligomer-type and polymer-type compounds having a benzophenone structure.
  • benzophenone-based antioxidant examples include Tomisorp 800 (manufactured by API Corporation) and LA-51 (manufactured by Asahi Denka Kogyo Co., Ltd.).
  • triazine antioxidant examples include 2,4-bis (allyl) -6- (2-hydroxyphenyl) 1,3,5-triazine.
  • Other examples include oligomer type and polymer type compounds having a triazine structure.
  • triazine antioxidant examples include CYASORBS UV-1164 (manufactured by Sun Chemical Co., Ltd.).
  • hydroxylamine antioxidant examples include IRGASTABFS042 (above, manufactured by BASF Japan Ltd.).
  • salicylate-based antioxidant examples include phenyl salicylate, p-octylphenyl salicylate, p-tertbutylphenyl salicylate, and the like.
  • Other examples include oligomer type and polymer type compounds having a salicylate structure.
  • antioxidants can be used singly or as a mixture of two or more at any ratio as required.
  • the content of the antioxidant is more preferably 0.5 to 5.0% by weight based on the solid content weight of the color filter coloring composition, since the brightness and sensitivity are good.
  • One embodiment of the coloring composition for a color filter may contain an amine compound that functions to reduce dissolved oxygen.
  • amine compounds examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.
  • the content of the amine compound is preferably 0.5 to 5.0% by weight from the viewpoint of brightness and sensitivity, based on the solid content of the color filter coloring composition (100% by weight).
  • a leveling agent is preferably added in order to improve the leveling property of the composition on the transparent substrate.
  • the leveling agent dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable.
  • dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by BYK Chemie.
  • dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie.
  • Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination.
  • the leveling agent content is preferably 0.003 to 0.5% by weight based on the total weight of the coloring composition (100% by weight).
  • a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule. Specifically, although it has a hydrophilic group, its solubility in water is small, and when added to a colored composition, its surface tension reducing ability is low, and even though it has low surface tension reducing ability, it can be applied to a glass plate. Those having good wettability and capable of sufficiently suppressing the chargeability at an addition amount that does not cause defects in the coating film due to foaming are preferable.
  • dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit. Dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
  • the bonding form of polyalkylene oxide units with dimethylpolysiloxane is as follows: pendant type in which polyalkylene oxide units are bonded in repeating units of dimethylpolysiloxane, terminal-modified type in which the end of dimethylpolysiloxane is bonded, and alternating with dimethylpolysiloxane. Any of a linear block copolymer type bonded repeatedly may be used.
  • Dimethylpolysiloxanes having polyalkylene oxide units are commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
  • ⁇ Anionic, cationic, nonionic or amphoteric surfactants can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
  • anionic surfactant examples include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, monoethanolamine laurylsulfate , Lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, and the like.
  • Nonionic surfactants include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate, etc.
  • amphoteric surfactants such as alkylbetaines such as alkyldimethylaminoacetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.
  • One embodiment of the color filter coloring composition may contain a curing agent, a curing accelerator, and the like as necessary in order to assist the curing of the thermosetting resin.
  • a curing agent phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Of these, compounds having two or more phenolic hydroxyl groups in one molecule and amine curing agents are preferred. These may be used alone or in combination of two or more.
  • the content of the curing agent is preferably 0.01 to 15% by weight with respect to the total amount of the thermosetting resin.
  • the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl- N, N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (eg, triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (eg, dimethylamine, etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg, imidazole) 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2
  • One embodiment of the color filter coloring composition may contain other additive components as necessary.
  • a storage stabilizer can be included to stabilize the viscosity of the composition over time.
  • adhesion improving agents such as a silane coupling agent, can also be contained.
  • Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned.
  • the storage stabilizer can be used in an amount of 0.1 to 10% by weight based on the total amount of the colorant (100% by weight).
  • adhesion improver examples include vinyl silanes such as vinyl tris ( ⁇ -methoxyethoxy) silane, vinyl ethoxy silane and vinyl trimethoxy silane, (meth) acryl silanes such as ⁇ -methacryloxypropyl trimethoxy silane, ⁇ - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) methyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, N- ⁇ (aminoethyl) ⁇ -aminopropyltrime
  • a method for producing a colored composition (hereinafter also referred to as a pigment dispersion) is described below.
  • a mixture of a colorant containing a phthalocyanine compound represented by formula (1) or (3), a binder resin, and an organic solvent is dispersed and manufactured using a disperser.
  • the disperser include, but are not limited to, a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, and an attritor. It is preferable to add a dispersion aid during the dispersion, and other components may be added as necessary.
  • the specific aluminum phthalocyanine dye and other colorants may be simultaneously dispersed when the pigment dispersion is produced, or may be mixed after being separately dispersed.
  • the colorant when the colorant contains an aluminum phthalocyanine pigment and a pigment having an acidic group content of 100 to 600 ⁇ mol / g, it is preferably co-dispersed in the pigment carrier using a media type wet disperser.
  • Co-dispersion means that two or more pigments are mixed and dispersed together under the same conditions. By co-dispersing, it is possible to finely and finely disperse the pigment fine particles, and it is possible to produce a coloring composition for a color filter having excellent dispersion stability after dispersion.
  • the co-dispersing method is, for example, a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical type, in which at least two pigments are mixed with a dispersant and pre-dispersed with a homogenizer or the like. It can be carried out by dispersing by various dispersing means such as a sand mill, an annular bead mill, or an attritor. Especially, it is preferable to perform co-dispersion using a media type wet disperser.
  • the dispersed particle diameter becomes smaller as the dispersion proceeds, the transparency increases, and the contrast ratio increases.
  • a good contrast ratio can be obtained from about 300 nm.
  • the dispersion progresses and the dispersed particle size becomes small the viscosity of the dispersion increases and the thixotropic property tends to increase.
  • the dispersed particle size it is preferable to suppress the dispersed particle size to about 100 nm in consideration of the viscosity and thixotropic property preferable for normal use.
  • a colorant having an average primary particle size of 100 nm or less and controlling the degree of dispersion so that the average particle size of the dispersed particles is within the range of 50 nm to 150 nm the increase in viscosity and thixotropic property are minimized.
  • a colorant dispersion with a very high contrast ratio can be obtained.
  • solubility of the colorant is high, specifically, the solubility in the solvent to be used is high, and if it is dissolved by stirring and no foreign matter is confirmed, it is necessary to manufacture by finely dispersing as described above. There is no.
  • the obtained colored composition is subjected to centrifugal separation or filtration using a sintered filter, a membrane filter or the like, so that coarse particles of 5 ⁇ m or more, preferably coarse particles of 1 ⁇ m or more, more preferably coarse particles of 0.5 ⁇ m or more. It is preferable to remove the mixed dust.
  • a coloring composition does not contain a particle
  • the coloring composition from which coarse particles have been removed as required can be prepared as a solvent developing type or alkali developing type coloring composition.
  • the solvent development type or alkali development type coloring composition is prepared by mixing a pigment dispersion and a photopolymerizable monomer, a photopolymerization initiator, a solvent, a dispersion aid, an additive, and the like selected as necessary. Can be adjusted.
  • the photopolymerization initiator may be added at the stage of preparing the colored composition, or may be added later to the prepared colored composition.
  • a color filter comprises a filter segment formed using one embodiment of a colored composition for a color filter.
  • the color filter examples include those having a red filter segment, a green filter segment, and a blue filter segment.
  • the color filter may further comprise a magenta filter segment, a cyan filter segment, and a yellow filter segment, and the cyan filter segment is formed from the colored composition of the present invention. It may be.
  • the filter segment After applying the photosensitive coloring composition for the color filter by spin coating method or die coating method, the filter segment is irradiated with an active energy ray such as ultraviolet ray to cure the portion that becomes the filter segment, and then developing the substrate. Formed on top.
  • the color filter coloring composition is used to form a green filter segment, and the other color filter segments are formed using a conventionally used red photosensitive coloring composition, blue photosensitive coloring composition, or the like. Can do.
  • each color photosensitive coloring composition other than the photosensitive coloring composition for color filters other than green each normal photosensitive coloring composition containing each colorant, the resin, the photopolymerizable composition, and the like is used. Can be formed.
  • the red filter segment can be formed using a normal red coloring composition containing a red pigment and a pigment carrier.
  • the red coloring composition include C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 146, 168, 169, 177, 178, 184, 185, 187, 200, 202, 208, 210, 242, 246, 254, 255, 264, 270, 272, 273, 274, 276, 277, 278, 279, 280, Red pigments such as 281, 282, 283, 284, 285, 286, or 287 are used.
  • a basic dye or a salt-forming compound of an acid dye exhibiting a red color can also be used.
  • red dyes such as xanthene, azo, disazo, and anthraquinone. More specifically, C.I. I. Examples thereof include salt-forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338.
  • C.I. I. Blue pigments such as CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64 are used.
  • I. Purple pigments such as CI pigment violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 can be used in combination.
  • a basic dye or a salt forming compound of an acidic dye that exhibits blue or purple can be used.
  • a triarylmethane dye or a xanthene dye is preferable in terms of lightness.
  • glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali aluminoborosilicate glass, and resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate are used.
  • resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate are used.
  • a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
  • One embodiment of the color filter can be manufactured by a printing method or a photolithography method.
  • filter segments by printing methods allows patterning by simply printing and drying the colored composition prepared as a printing ink, making it a low cost and excellent mass productivity as a color filter manufacturing method. Yes. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Further, it is important to control the fluidity of the ink on the printing press, and the viscosity of the ink can be adjusted with a dispersant or extender pigment.
  • the photosensitive coloring composition prepared as the solvent developing type or alkali developing type coloring resist material is spray coated, spin coated, slit coated, roll coated, etc. on a transparent substrate.
  • the coating method is applied so that the dry film thickness is 0.2 to 5 ⁇ m. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.
  • an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used.
  • an antifoamer and surfactant can also be added to a developing solution.
  • a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Then, ultraviolet exposure can be performed.
  • the color filter can be manufactured by an electrodeposition method, a transfer method, an ink jet method or the like in addition to the above method.
  • the electrodeposition method is a method for producing a color filter by electrodepositing each color filter segment on a transparent conductive film by electrophoresis of colloidal particles using a transparent conductive film formed on a substrate.
  • the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.
  • a black matrix can be formed in advance before forming each color filter segment on a transparent substrate or a reflective substrate.
  • a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto.
  • a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment may be formed.
  • an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention as necessary.
  • the color filter is bonded to the counter substrate using a sealant, and after injecting liquid crystal from the injection port provided in the seal part, the injection port is sealed, and if necessary, a polarizing film or a retardation film is placed outside the substrate.
  • a liquid crystal display panel is manufactured by bonding.
  • Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convented bend (OCB). It can be used in a liquid crystal display mode in which colorization is performed using a color filter such as the above.
  • Embodiments I to VII will be described below based on examples, but the present invention is not limited thereto.
  • Parts means “parts by weight” and “%” means “% by weight”.
  • PGMAC means propylene glycol monomethyl ether acetate.
  • the number average molecular weight and the weight average molecular weight were determined by connecting four separation columns in series in the gel permeation chromatography (GPC) “HLC-8120GPC” manufactured by Tosoh Corporation, and the packing materials in order.
  • GPC gel permeation chromatography
  • the volume average primary particle diameter (MV) of the colorant is obtained by measuring the short axis diameter and the long axis diameter of the primary particles of 100 pigments using a transmission electron microscope (TEM) photograph. Assuming that the average of the major axis diameter is the particle size (d) of the colorant particles, and then assuming that each colorant is a sphere having the determined particle size, the volume (V) of each particle is determined. The calculation was performed on 100 colorant particles, and the calculation was performed using the following calculation formula (I-1).
  • ⁇ Binder resin production method> (Preparation of binder resin solution) 233 parts of propylene glycol monomethyl ether acetate was charged into a separable four-necked flask equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, a dropping pipe and a stirring device, and the temperature was raised to 80 ° C.
  • a phthalocyanine compound (a) 100 parts of hydroxyaluminum phthalocyanine and 49.5 parts of diphenyl phosphate obtained in 1000 parts of methanol were added in a reaction vessel, heated to 40 ° C., and reacted for 8 hours. After cooling this to room temperature, the product was filtered, washed with methanol, and then dried to obtain 114 parts of a phthalocyanine compound (a).
  • the phthalocyanine represented by the formula (a) is as described in the column of the embodiment for carrying out the invention.
  • a salt milling treatment of the phthalocyanine compound (a) was performed. 100 parts of the phthalocyanine compound (a), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. Next, the kneaded product is poured into 3000 parts of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, 98 parts of a blue colorant (I-PB-1) was obtained. The obtained colorant had a volume average primary particle size of 31 nm.
  • phthalocyanine compound (b) and blue colorant (I-PB-2) In the synthesis of the phthalocyanine compound (a), a phthalocyanine compound (b) was obtained in the same manner except that 43.2 parts of diphenylphosphinic acid was used instead of diphenyl phosphate. Subsequently, a blue colorant (I-PB-2) was produced in the same manner as the blue colorant (I-PB-1). The obtained colorant had a volume average primary particle size of 29 nm.
  • the phthalocyanine represented by the formula (b) is as described in the column of the embodiment for carrying out the invention.
  • phthalocyanine compound (c) and blue colorant (I-PB-3) The phthalocyanine compound (a) was synthesized in the same manner except that 250 parts of 4-methylphthalodinitrile was used in place of phthalodinitrile and 28.0 parts of phenylphosphinic acid was used in place of diphenyl phosphate. (C) was obtained. Subsequently, a blue colorant (I-PB-3) was produced in the same manner as the blue colorant (I-PB-1). The obtained colorant had a volume average primary particle size of 33 nm.
  • the phthalocyanine represented by the formula (c) is as described in the column of the embodiment for carrying out the invention.
  • phthalocyanine compound (d) and blue colorant (I-PB-4) The phthalocyanine compound (a) was synthesized in the same manner except that 285 parts of 4-chlorophthalodinitrile was used instead of phthalodinitrile and 41.5 parts of dibutyl phosphate was used instead of diphenyl phosphate. (D) was obtained. Subsequently, a blue colorant (I-PB-4) was produced in the same manner as the blue colorant (I-PB-1). The obtained colorant had a volume average primary particle size of 28 nm.
  • the phthalocyanine represented by the formula (d) is as described in the column of the embodiment for carrying out the invention.
  • Preparation of yellow coloring composition (Preparation of yellow coloring composition (I-DY-1)) After stirring and mixing the mixture having the following composition to be uniform, using a zirconia bead having a diameter of 0.5 mm, using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After dispersing for 4 hours, a pigment content of 50% and a solid content of 20% were prepared to prepare a yellow coloring composition (I-DY-1). Yellow colorant (I-PY-1) 10.0 parts Binder resin solution 50.0 parts PGMAC 40.0 parts
  • the coated substrate having the chromaticity shown in Table I-1 was obtained.
  • a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.) was used for chromaticity measurement.
  • Example I-8 Production of (I-DG-1)
  • the blue colored composition (I-DB-1) and the yellow colored composition (I-DY-1) produced above were used to form a coating substrate.
  • Preparation of [Examples I-9 to I-11, Reference Examples I-4 to I-6] (I-DG-2 to 7) (I-DG-2 to 7)
  • the blue coloring composition and the yellow coloring composition shown in Table I-2 were used.
  • the green color compositions (I-DG-2 to 7) were prepared in the same manner as (I-DG-1) by changing the chromaticity as described in the table.
  • the blue coloring composition using the phthalocyanine compound represented by the formula (1) as a colorant includes hydroxyaluminum phthalocyanine and siloxyphthalocyanine represented by the formula (I-2). Compared to the blue coloring composition using the compound (Reference Examples I-1 to I-3), the color difference after evaluation of heat resistance and light resistance was small.
  • the green coloring composition using the phthalocyanine compound represented by the formula (1) and a yellow pigment as a colorant has a small color difference after evaluation of heat resistance and light resistance. At the same time, good results were obtained in terms of foreign matter generation and viscosity.
  • the green coloring composition using Pigment Yellow 185 (Examples I-8, I-9, I-11 to I-14) is particularly heat and light resistant compared to Example I-10 using other yellow pigments. The result was high.
  • the produced substrate had a chromaticity with a C light source shown in Table I-5 after heat treatment at 230 ° C.
  • Examples I-1 to I-14 were prepared using the above substrates prepared using the photosensitive coloring compositions obtained in Examples I-15 to I-20 and Reference Examples I-9 to I-12. The same evaluations as in Reference Examples I-1 to I-8 were performed.
  • Examples I-1 to I-14 were prepared using the above substrates prepared using the photosensitive coloring compositions obtained in Examples I-15 to I-20 and Reference Examples I-9 to I-12. The same evaluations as in Reference Examples I-1 to I-8 were performed.
  • the photosensitive coloring composition using the phthalocyanine compound represented by the formula (1) as a colorant is the coloring composition shown in Examples I-1 to I-14.
  • the photosensitive coloring composition containing hydroxyaluminum phthalocyanine generally resulted in poor heat resistance and light resistance.
  • the film was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • the average primary particle diameter of the pigment, the acidic group amount of the pigment, the weight average molecular weight (Mw) of the resin, the average molecular weight of the basic resin type dispersant, and the amine value of the basic resin type dispersant are as follows. is there.
  • the average primary particle diameter of the pigment was measured by a method of directly measuring the size of primary particles from an electron micrograph using a transmission (TEM) electron microscope. Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the primary pigment particles. Next, for 100 or more pigment particles, the volume (weight) of each particle was obtained by approximating the obtained particle size cube, and the volume average particle size was defined as the average primary particle size.
  • the amine adsorption amount was measured as the acidic group amount of the pigment.
  • 1 g of the pigment was measured in a glass container that could be sealed, and 30 ml of a propylene glycol monomethyl ether acetate solution of 0.02 mol / l n-hexylamine (adsorbent) was added.
  • the vessel was capped and placed on an ultrasonic cleaner for 1 hour to adsorb on the pigment surface, and then centrifuged to obtain the supernatant.
  • Weight average molecular weight of resin (Mw) The weight average molecular weight (Mw) of the resin was measured using HLC-8220GPC (manufactured by Tosoh Corporation) as an apparatus, TSK-GEL SUPER HZM-N connected in series as a column, and THF as a solvent. The molecular weight in terms of polystyrene.
  • the number average molecular weight (Mn) and the weight average molecular weight (Mw) of the basic resin type dispersant are HLC-8320GPC (manufactured by Tosoh Corporation) as an apparatus, SUPER-AW3000 as a column, and 30 mM triethylamine as an eluent. And polystyrene-equivalent number average molecular weight (Mn) and weight average molecular weight (Mw) measured using an N, N-dimethylformamide solution of 10 mM LiBr.
  • the amine value of the basic resin type dispersant is a value obtained by converting the total amine value (mgKOH / g) measured in accordance with the method of ASTM D 2074 into a solid content.
  • an acrylic resin solution II-2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • the resulting aluminum phthalocyanine pigment represented by the formula (II-3) was subjected to the same salt milling method as the blue colorant (II-PB-1) to obtain a blue colorant (II-PB-2). .
  • the average primary particle size was 29.5 nm.
  • the resulting aluminum phthalocyanine pigment represented by the formula (II-4) was subjected to the same salt milling method as the blue colorant (II-PB-1) to obtain a blue colorant (II-PB-3). .
  • the average primary particle size was 29.5 nm.
  • the resulting aluminum phthalocyanine pigment represented by the formula (II-5) was subjected to the same salt milling method as the blue colorant (II-PB-1) to obtain a blue colorant (II-B-4). .
  • the average primary particle size was 33.0 nm.
  • Base resin type dispersant solution 1 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 96.1 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed from the solid content of the polymerization that the polymerization yield is 95% or more, and 3.9 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • Base resin type dispersant solution 2 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 88.0 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed that the polymerization yield is 95% or more from the solid content of the polymerization, and 12.0 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • the polymerization solution is sampled, and it is confirmed from the solid content of the polymerization that the polymerization yield is 95% or more, and 24.0 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • Base resin type dispersant solution 4 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 70.7 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed from the solid content of the polymerization that the polymerization yield is 95% or more, and 29.3 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • Base resin type dispersant solution 5 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 41.4 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed that the polymerization yield is 95% or more from the solid content of the polymerization, and 58.6 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • Base resin type dispersant solution 6 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 18.2 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed that the polymerization yield is 95% or more from the solid content of the polymerization, and 81.8 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • Base resin type dispersant solution 7 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 98.2 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed from the solid content of the polymerization that the polymerization yield is 95% or more, and 2.0 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • Base resin type dispersant solution 8 A four-necked separable flask equipped with a thermometer, stirrer, distillation tube, and condenser was charged with 70 parts of methyl ethyl ketone, 13.8 parts of n-butyl acrylate, 2.8 parts of sparteine, and 1.9 parts of ethyl bromoisobutyrate. The temperature was raised to 40 ° C. under a nitrogen stream. 1.1 parts of cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution is sampled, and it is confirmed from the solid content of the polymerization that the polymerization yield is 95% or more, and 86.2 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK are added. Further, polymerization was performed. After 2 hours, it was confirmed that the polymerization yield was 97% or more from the solid content of the polymerization solution, and the polymerization was stopped by cooling to room temperature. 100 parts of the obtained resin solution was diluted with 100 parts of methyl ethyl ketone, 60 parts of cation exchange resin “Diaion PK228LH (Mitsubishi Chemical Corporation)” was added and stirred at room temperature for 1 hour.
  • the yellow coloring agent 1 shown in the preparation method of the yellow coloring composition 1 is colored in the coloring agent (P-2) (CI pigment yellow 139) in the yellow coloring composition 2, and colored in the yellow coloring composition 3.
  • Example II-1 (Preparation of colored composition 1) After stirring and mixing the mixture having the following composition to be uniform, using a zirconia bead having a diameter of 0.5 mm, using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After dispersing for 4 hours, the mixture was filtered with a 5 ⁇ m filter to prepare Colored Composition 1. Colorant 1; Blue colorant (II-PB-1) 8.0 parts Colorant 2; Colorant (P-1) 2.0 parts Acrylic resin solution II-1 25.0 parts Basic resin type dispersant solution 3 8.3 parts Organic solvent (PGMAC) 56.7 parts
  • Examples II-2 to II-14 (Preparation of colored compositions 2 to 14)
  • the coloring composition is the same as the coloring composition 1 except that the types of the coloring agent 1, the coloring agent 2, and the basic resin type dispersing agent solution 3 in the preparation method of the coloring composition 1 are changed as shown in Table II-5. Items 2 to 14 were produced.
  • Example II-15 (Preparation of colored composition 15) After stirring and mixing the mixture having the following composition to be uniform, using a zirconia bead having a diameter of 0.5 mm, using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After dispersing for 4 hours, the mixture was filtered with a 5 ⁇ m filter to prepare a colored composition 15. Colorant 1; Blue colorant (II-PB-2) 7.2 parts Colorant 2; Colorant (P-1) 1.8 parts Acrylic resin solution II-1 25.0 parts Basic resin type dispersant solution 3 8.3 parts Organic solvent (PGMAC) 56.7 parts Dye derivative 1 1.0 part
  • Example II-16 (Preparation of colored composition 16) The same procedure as in the color composition 15 except that the types of the colorant 1, the colorant 2, the basic resin type dispersant solution 3, and the pigment derivative in the method for producing the color composition 15 were changed as shown in Table II-5. Thus, a colored composition 16 was produced.
  • Example II-17 (Preparation of colored composition 17) After stirring and mixing the mixture having the following composition to be uniform, using a zirconia bead having a diameter of 0.5 mm, using an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) as a media type wet disperser. After dispersing for 4 hours, the mixture was filtered through a 5 ⁇ m filter to prepare a colored composition 17 (a).
  • the coloring composition is the same as the coloring composition 18 except that the types of the coloring agent 1, the coloring agent 2, and the basic resin type dispersing agent solution in the preparation method of the coloring composition 18 are changed as shown in Table II-5. 19 to 21 were produced.
  • the viscosity characteristics of the coloring composition can be evaluated by the initial viscosity and the rate of increase in viscosity over time.
  • the viscosity of the coloring compositions 1 to 22 was measured at 25 ° C. on the adjustment day using an E type viscometer (“ELD type viscometer” manufactured by Toki Sangyo Co., Ltd.) at a rotation speed of 20 rpm. The evaluation results were evaluated as follows.
  • the light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate. At this time, if the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the colored composition, scattering or the like occurs by the colorant particles, and when a part of the polarization plane is displaced, the polarizing plate is transmitted in parallel.
  • an initial contrast ratio (initial CR) was evaluated.
  • the coloring compositions 1 to 22 are applied on a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, then dried at 70 ° C. for 20 minutes, and then heated at 220 ° C. for 30 minutes and allowed to cool. Thus, a coated substrate was produced.
  • the initial contrast ratio (initial CR) of the obtained coated substrate was measured.
  • a coating film was prepared by adjusting the spin coater coating conditions so that the film thickness measured using a surface shape measuring device “Dektak 8 (manufactured by Veeco)” was 1 ⁇ m. .
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate. In the measurement, the measurement was performed through a black mask having a 1 cm square hole in the measurement portion. *
  • the evaluation results were evaluated as follows. ⁇ : 97.5% or more ⁇ : 95.0% or more to less than 97.5% X: Less than 95.0%
  • a coloring composition for a color filter containing a phthalocyanine pigment having a specific structure and a pigment having an acidic group content of 100 to 600 ⁇ mol / g has viscosity characteristics (initial viscosity). The rate of increase in viscosity with time) and the rate of change in contrast ratio with time were good results.
  • a coloring composition obtained by co-dispersing a phthalocyanine pigment having a specific structure and a pigment having an acidic group amount of 100 to 600 ⁇ mol / g does not co-disperse.
  • the viscosity characteristics (initial viscosity, rate of increase in viscosity with time) and contrast ratio change rate with time were good.
  • Example II-18 (Preparation of photosensitive coloring composition 1) A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 ⁇ m filter to prepare a photosensitive coloring composition 1.
  • Coloring composition 1 30.0 parts Yellow coloring composition 1 30.0 parts
  • Photopolymerizable monomer 3.0 parts (“Aronix M402" manufactured by Toagosei Co., Ltd.)
  • Acrylic resin solution II-2 14.9 parts
  • 1.6 parts of photopolymerization initiator (“Irgacure 379” manufactured by Ciba Japan)
  • Photopolymerizable monomer Dipentaerythritol hexaacrylate / pentaacrylate mixture (“Aronix M402” manufactured by Toagosei Co., Ltd.)
  • Photopolymerization initiator A 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (“Irga” manufactured by Ciba Japan) Cure 379 ")
  • Photopolymerization initiator B Ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (0-acetyloxime) ("Irgacure OXE02" manufactured by Ciba Japan)
  • Sensitizer 4,4′-diethylaminobenzophenone (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) Anti
  • the photosensitive coloring compositions 1 to 25 were evaluated for the viscosity characteristics (initial viscosity, viscosity increase rate with time) and the contrast ratio change rate with time by the following methods. The results are shown in Table II-8.
  • the photosensitive coloring compositions 1 to 25 are coated on a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, dried at 70 ° C. for 20 minutes, and integrated light quantity using an ultrahigh pressure mercury lamp. UV exposure was performed at 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Subsequently, it heated at 220 degreeC for 30 minute (s), and the coating-film board
  • a coating film was prepared by adjusting the spin coater coating conditions so that the film thickness measured using a surface shape measuring device “Dektak 8 (manufactured by Veeco)” was 2 ⁇ m. .
  • a surface shape measuring device “Dektak 8 (manufactured by Veeco)” was 2 ⁇ m.
  • an alkaline developer sodium carbonate 1.5% by weight, sodium hydrogen carbonate 0.5% by weight, an anionic surfactant ("PERI-LEX NBL” manufactured by Kao Corporation) and water 90% by weight. What was used.
  • the initial contrast ratio (initial CR) of the obtained substrate was measured by the same method as the evaluation of the colored composition.
  • time-dependent contrast ratio (time-dependent CR) of the photosensitive coloring compositions 1 to 25 accelerated for one week at 40 ° C. was measured by the same method as the initial contrast ratio (initial CR).
  • the rate of change in contrast ratio with time was measured by the same method as the evaluation of the colored composition.
  • the evaluation criteria at that time were as follows. ⁇ : 97.5% or more ⁇ : 95.0% or more and less than 97.5% X: Less than 95.0%
  • a photosensitive coloring composition for a color filter containing a phthalocyanine pigment having a specific structure and a pigment having an acidic group content of 100 to 600 ⁇ mol / g has viscosity characteristics ( The initial viscosity, the rate of increase in viscosity with time, and the rate of change in contrast ratio with time were good results.
  • a colored composition obtained by co-dispersing a phthalocyanine pigment having a specific structure and a pigment having an acidic group amount of 100 to 600 ⁇ mol / g does not co-disperse.
  • the viscosity characteristics (initial viscosity, viscosity increase rate with time) and contrast ratio change rate with time were good results.
  • the red photosensitive coloring composition and the blue photosensitive coloring composition used for preparation of a color filter were produced.
  • the photosensitive coloring composition 2 was used about green.
  • red photosensitive coloring composition (II-RR-1)) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a red colored composition (II-DR-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Red pigment (CI Pigment Red 254) 9.6 parts Red Pigment (CI Pigment Red 177) 2.4 parts
  • Resin-type dispersant (“EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution II-1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • red photosensitive coloring composition (II-RR-1).
  • Red coloring composition (II-DR-1) 42.0 parts Acrylic resin solution II-2 13.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts
  • Photopolymerization initiator Ciba Japan "Irgacure 907" 2.0 parts
  • Sensitizer Hodogaya Chemical "EAB-F"
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a blue photosensitive coloring composition (II-RB-1).
  • Blue coloring composition II-DB-6
  • Acrylic resin solution II-2 15.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.)
  • Photopolymerization initiator "Irgacure 907" manufactured by Ciba Japan Co., Ltd.) 2.0 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • a colored coating was formed.
  • the coating was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • RB-1 blue photosensitive coloring composition
  • hydroxyaluminum phthalocyanine III-2 (Production of hydroxyaluminum phthalocyanine III-2)
  • hydroxyaluminum phthalocyanine represented by the following formula (III-2) was prepared in the same manner except that 250 parts of 4-methylphthalodinitrile was used instead of phthalodinitrile. III-2 was obtained.
  • a salt milling process was performed. 100 parts of the specific phthalocyanine dye represented by the formula (a), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. The kneaded product was poured into 3000 parts of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. all day and night. 98 parts of colorant (III-A-1) were obtained. The average primary particle size was 31.2 nm.
  • Step 2 Reaction to epoxy group
  • the inside of the flask was purged with air, and 17.0 parts of acrylic acid and 0.3 part of trisdimethylaminomethylphenol and 0.3 part of hydroquinone were added as catalysts required for the reaction of the precursor at this stage, Reaction was performed for 5 hours, and the resin solution whose weight average molecular weight is about 12000 (measurement by GPC) was obtained.
  • the added acrylic acid is ester-bonded to the end of the epoxy group of the glycidyl methacrylate structural unit, so that no carboxyl group is generated in the resin structure.
  • Step 3 Reaction to hydroxyl group
  • 30.4 parts of tetrahydrophthalic anhydride and 0.5 part of triethylamine as a catalyst required for the reaction of the precursor at this stage were added and reacted at 120 ° C. for 4 hours.
  • the added tetrahydrophthalic anhydride one of two carboxyl groups generated by cleavage of the carboxylic anhydride moiety is ester-bonded to a hydroxyl group in the resin structure, and the other produces a carboxyl group terminal.
  • Step 4 Adjustment of nonvolatile content
  • Propylene glycol monomethyl ether acetate was added so that the nonvolatile content was 40% to obtain a resin solution (B1-1).
  • the weight ratio of the structural unit in the resin solution (B1-1) was as follows: tetrahydrophthalic anhydride as the structural unit (b1); 21.7% by weight, styrene as the structural unit (b2); 11.6% by weight, structural unit (b3 ) As dicyclopentanyl methacrylate; 29.3% by weight; as other structural units, the total of glycidyl methacrylate and acrylic acid ester-bonded to the glycidyl terminal; 37.4% by weight.
  • Resin solutions (B1-2-3 and B2-1) Resin solutions (B1-2) to (B1-3) and (B2-1) were obtained in the same manner as the resin solution (B1-1). That is, in the production method of the resin solution (B1-1), the precursors corresponding to the structural units (b1) to (b4) and other structural units were replaced according to Table III-1. The number of catalyst parts required for each stage was mixed in proportion to the total number of precursors mixed in each stage.
  • Resin solution (B1-4 to 5) Resin solutions (B1-4) to (B1-5) were obtained in the same manner as in steps 1, 2, and 4 of resin solution (B1-1). That is, in the production method of the resin solution (B1-1), the precursors corresponding to the structural units (b1) to (b4) and other structural units were replaced according to Table III-1. The precursor corresponding to MAA (methacrylic acid) in the structural units (b1) to (b3) and the structural unit (b4) is mixed to carry out the production step 1, and then GMA (glycidyl methacrylate) is used as the precursor. In addition, stage 2 of the production was carried out and stage 4 was further carried out. The number of catalyst parts required for each stage was mixed in proportion to the total number of precursors mixed in each stage.
  • MAA methacrylic acid
  • GMA glycol methacrylate
  • Resin solution (B2-2) was prepared in the same manner as in steps 1, 2, and 4 of resin solution (B1-1). That is, in the production method of the resin solution (B1-1), the precursors corresponding to the structural units (b1) to (b4) and other structural units were replaced according to Table III-1. GMA (glycidyl methacrylate) in the structural unit (b2), the structural unit (b4), and other precursors corresponding to the other structural units are mixed to perform Step 1 of production, and then AA (acrylic acid) is the precursor. In addition, stage 2 of the manufacturing was carried out and stage 4 was further carried out. The number of catalyst parts required for each stage was mixed in proportion to the total number of precursors mixed in each stage.
  • GMA glycol methacrylate
  • AA acrylic acid
  • composition and weight ratio of the obtained resin solution (B1-1 to 5) and resin solution (B2-1 to 2) are shown in Table III-1.
  • the value in parentheses represents the weight ratio (% by weight) of the constituent unit in the resin solid content.
  • MAA methacrylic acid
  • THPA tetrahydrophthalic anhydride (4-cyclohexene-1,2-dicarboxylic anhydride)
  • BzMA Benzyl methacrylate St: Styrene M110: Paracumylphenol ethylene oxide modified acrylate
  • DCPMA Dicyclopentanyl methacrylate
  • GMA Glycidyl methacrylate
  • GMA-AA Condensation unit
  • MMA-GMA Structural unit
  • BMA n-butyl methacrylate
  • HEMA 2-hydroxyethyl methacrylate
  • Example III-1 Green coloring composition (III-DG-1))
  • Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a green colored composition (III-DG-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • the ratio of -1) was selected.
  • Example III-2 Green coloring composition (III-DG-2) Except for changing the blue colorant (III-A-1) to the blue colorant (III-A-2), in the same manner as the green color composition (III-DG-1), the green color composition (III- DG-2) was obtained.
  • Example III-3 Green coloring composition (III-DG-3)
  • the green coloring composition (III-DG-1) was changed in the same manner as the green coloring composition (III-DG-1) except that the blue coloring agent (III-A-1) was changed to the blue coloring agent (III-A-3).
  • DG-3) was obtained.
  • the light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the coating film of the colored composition applied on the glass substrate, and reaches the other polarizing plate. At this time, if the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light is transmitted through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the colored composition, scattering or the like occurs by the colorant particles, and when a part of the polarization plane is displaced, the polarizing plate is transmitted in parallel.
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate.
  • NPF-G1220DUN manufactured by Nitto Denko Corporation
  • the measurement was performed through a black mask having a 1 cm square hole in the measurement portion.
  • the green coloring composition (III-DG-1 to 13) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater, then dried at 70 ° C. for 20 minutes, and then 220 ° C. A coating film substrate was produced by heating and cooling for 30 minutes.
  • the contrast ratio (CR) of the obtained coated substrate was measured.
  • the contrast ratio was determined according to the following criteria. ⁇ : 4000 or more ⁇ : 3500 to less than 4000 ⁇ : less than 3500
  • OSP-SP100 microspectrophotometer
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 )
  • ⁇ Eab * is less than 3.0 ⁇ : ⁇ Eab * is less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more and less than 10.0 ⁇ : ⁇ Eab * is 10.0 or more
  • each of the color filter coloring compositions containing a phthalocyanine dye having a specific structure and a binder resin having a specific structure has a high contrast ratio and excellent heat resistance. It was the result.
  • Green photosensitive coloring composition (III-RG-1) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 1.0 ⁇ m filter to obtain a green photosensitive coloring composition (III-RG-1).
  • Green coloring composition (III-DG-1) 55.0 parts Acrylic resin solution (B1-1) 9.2 parts Photopolymerizable monomer (“Aronix M402” manufactured by Toagosei Co., Ltd.
  • Example III-10 Green photosensitive coloring composition (III-RG-2) Except for changing the green coloring composition (III-DG-1) to the green coloring composition (III-DG-2), the green photosensitive coloring composition (III-RG-2) was obtained in the same manner as in Example III-9. Got.
  • Example III-11 Green photosensitive coloring composition (III-RG-3) Except for changing the green coloring composition (III-DG-1) to the green coloring composition (III-DG-3), in the same manner as in Example III-9, the green photosensitive coloring composition (III-RG-3) Got.
  • Example III-12 to III-17 Reference Examples III-6 to III-11
  • Green photosensitive coloring composition (III-RG-4 to 15) Example III, except that the green coloring composition (III-DG-1) and / or acrylic resin solution (B1-1) was changed to the green coloring composition and / or acrylic resin solution shown in Table III-3. Green photosensitive coloring compositions (III-RG-4 to 15) were obtained in the same manner as -9.
  • the green photosensitive coloring composition (III-RG-1 to 15) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater, and then dried at 70 ° C. for 20 minutes. Using a high-pressure mercury lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Then, after heating at 220 ° C. for 30 minutes and allowing to cool, the contrast ratio (CR) of the obtained coating film substrate was measured by the same method as the evaluation of the colored composition.
  • CR contrast ratio
  • the alkali developer was 1.5% by weight of sodium carbonate, 0.5% by weight of sodium hydrogen carbonate, 8.0% by weight of an anionic surfactant (“Perex NBL” manufactured by Kao Corporation), and 90% by weight of water. The thing which consists of was used.
  • the contrast ratio was determined according to the following criteria. ⁇ : 4000 or more ⁇ : 3500 to less than 4000 ⁇ : less than 3500
  • the green photosensitive coloring composition (III-RG-1 to 15) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater, and then dried at 70 ° C. for 20 minutes. Using a high-pressure mercury lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. Subsequently, it heated at 220 degreeC for 30 minute (s), and after standing to cool, the coating-film board
  • substrate was obtained. The prepared coated substrate was adjusted to a chromaticity of y 0.600 with a C light source after heat treatment at 220 ° C.
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 230 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ⁇ Eab * was determined and evaluated in the following four stages.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 )
  • the green photosensitive coloring composition (III-RG-1 to 15) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater at a rotation speed at which the film thickness after drying was 2 ⁇ m.
  • the substrate was dried at 70 ° C. for 20 minutes and spray-developed using a sodium carbonate aqueous solution at 23 ° C., and the developability was evaluated in four stages.
  • the alkali developer was 1.5% by weight of sodium carbonate, 0.5% by weight of sodium hydrogen carbonate, 8.0% by weight of an anionic surfactant (“Perex NBL” manufactured by Kao Corporation), and 90% by weight of water. The thing which consists of was used.
  • the developability evaluation was determined according to the following criteria. ⁇ : Can be completely removed within 30 seconds ⁇ : Over 30 seconds but completely removed within 33 seconds ⁇ : Over 33 seconds but completely removed within 36 seconds ⁇ : Over 36 seconds Can not be completely removed
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 230 ° C. for 330 minutes in a clean oven.
  • the spray development was performed in the shortest time during which a pattern can be formed without any development remaining on the coating film of each photosensitive coloring composition, and this was set as an appropriate development time.
  • the alkali developer was 1.5% by weight of sodium carbonate, 0.5% by weight of sodium hydrogen carbonate, 8.0% by weight of an anionic surfactant (“Perex NBL” manufactured by Kao Corporation), and 90% by weight of water. The thing which consists of was used.
  • the film thickness of the coating film was determined using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).
  • the pattern in the 25 ⁇ m photomask portion of the filter segment formed by the above method was evaluated by observing with an optical microscope.
  • the rank of evaluation is as follows.
  • the poor resolution means that adjacent stripe patterns are connected or chipped.
  • the resolution evaluation was determined according to the following criteria. ⁇ : Good resolution and linearity ⁇ : Slightly inferior in linearity but good resolution ⁇ : Partially poor resolution ⁇ : Poor resolution
  • the coloring composition for color filters containing a phthalocyanine dye having a specific structure and a binder resin having a specific structure obtained high-level evaluation results in all evaluations (Example III-9).
  • Example III-17 To Example III-17).
  • red photosensitive coloring composition III-RR-1
  • Eiger mill Mini Model M-250 MKII manufactured by Eiger Japan
  • zirconia beads having a diameter of 0.5 mm.
  • a red colored composition (III-DR-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Red pigment CI Pigment Red 254
  • Red Pigment CI Pigment Red 177)
  • Resin-type dispersant EFKA4300 manufactured by Ciba Japan
  • Resin solution B2-5) 17.5 parts Propylene glycol monomethyl ether acetate 69.5 parts
  • red photosensitive coloring composition III-RR-1
  • Red coloring composition III-DR-1
  • Resin solution B2-4
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.)
  • blue photosensitive coloring composition 1 (III-RB-1).
  • Blue coloring composition 1 (III-DB-1) 34.0 parts Resin solution (B2-4) 7.6 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts
  • Photopolymerization started Agent (“Irgacure 907” manufactured by Ciba Japan Co., Ltd.) 2.0 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 52.7 parts ethylene glycol monomethyl ether acetate
  • the film was irradiated with ultraviolet rays of 150 mJ / cm 2 through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 220 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • the color filter By using the green photosensitive coloring composition (III-RG-1), the color filter can be made to have a high CR, and other physical properties can be suitably used without any problem.
  • an acrylic resin solution IV-2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • a salt milling process was performed. 100 parts of the specific phthalocyanine dye represented by the formula (a), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. The kneaded product was poured into 3000 parts of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. all day and night. 98 parts of colorant (IV-B-1) were obtained. The average primary particle size was 31.2 nm.
  • Green pigment dispersion (IV-DG-1) Green pigment dispersion (IV-DG-1)
  • Eiger mill Mini Model M-250 MKII” manufactured by Eiger Japan
  • zirconia beads having a diameter of 0.5 mm.
  • a green pigment dispersion (IV-DG-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • the ratio of -1) was selected.
  • Carboxyl group-containing polyfunctional monomer (C1-2) In a 1 L four-necked flask, 515 parts of dipentaerythritol hexaacrylate, 50 parts of tetrahydrophthalic anhydride, and 0.5 part of N, N-dimethylbenzylamine are charged and reacted at a temperature of 80 to 100 ° C. for 10 hours.
  • the polyfunctional monomer (C1-2) containing a carboxyl group-containing polyfunctional monomer was obtained.
  • the acid value was 38, and the content of the carboxyl group-containing polyfunctional monomer was 40% in terms of area by gel permeation chromatography.
  • the double bond equivalent of the carboxyl group-containing polyfunctional monomer was 135.
  • Example IV-1 Green photosensitive coloring composition (IV-RG-1)) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 1.0 ⁇ m filter to obtain a green photosensitive coloring composition (IV-RG-1). Green pigment dispersion (IV-DG-1) 55.0 parts Acrylic resin solution IV-1 9.2 parts Carboxyl group-containing polyfunctional monomer (C1-1) 4.1 parts Photopolymerization initiator (manufactured by Ciba Japan) "Irgacure 379”) 1.9 parts PGMAC 29.8 parts
  • Photopolymerization initiator (G-1) Acetophenone photopolymerization initiator 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1 -Butanone ("Irgacure 379" manufactured by Ciba Japan)
  • Photopolymerization initiator (G-2) oxime ester photopolymerization initiator ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (0 -Acetyloxime) ("Irgacure OXE02" manufactured by Ciba Japan) ⁇
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 230 ° C. for 330 minutes in a clean oven.
  • the spray development was performed in the shortest time during which a pattern can be formed without any development remaining on the coating film of each photosensitive coloring composition, and this was set as an appropriate development time.
  • the alkali developer was 1.5% by weight of sodium carbonate, 0.5% by weight of sodium hydrogen carbonate, 8.0% by weight of an anionic surfactant (“Perex NBL” manufactured by Kao Corporation), and 90% by weight of water. The thing which consists of was used.
  • the film thickness of the coating film was measured using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).
  • forward tapered shape ⁇ 20 degrees ⁇ ⁇ ⁇ 35 degrees
  • forward tapered shape ⁇ 45 degrees ⁇ ⁇ 60 degrees
  • forward tapered shape ⁇ ⁇ > 60 degrees
  • the photosensitive coloring composition for a color filter containing a phthalocyanine dye having a specific structure and a polyfunctional monomer having an acid group all has developability, pattern shape, and resolution. Very good results were shown.
  • red photosensitive coloring composition (IV-RR-1)) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a red pigment dispersion (IV-DR-1) was prepared by filtration through a 0.0 ⁇ m filter. Red pigment (CI Pigment Red 254) 9.6 parts Red pigment (CI Pigment Red 177) 2.4 parts Resin-type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution IV-1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • red photosensitive coloring composition IV-RR-1
  • Red pigment dispersion IV-DR-1
  • Acrylic resin solution IV-2
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator ( Ciba Japan “Irgacure 907") 2.0 parts Sensitizer (Hodogaya Chemical "EAB-F”) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a blue photosensitive coloring composition (IV-RB-1).
  • Blue pigment dispersion (IV-DB-1) 34.0 parts Acrylic resin solution IV-2 15.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts
  • Photopolymerization initiator “Irgacure 907” manufactured by Ciba Japan Co., Ltd.) 2.0 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • the film was irradiated with ultraviolet rays of 150 mJ / cm 2 through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 220 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • the obtained color filter has good developability and image line-formability, and the coloring composition remains on the non-pixel portion on the substrate after development (development residue) and the pattern portion of the pixel portion is missing and / or peeled off. There was no.
  • an acrylic resin solution V-2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • a salt milling process was performed. 100 parts of the specific phthalocyanine dye represented by the formula (a), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. The kneaded product was poured into 3000 parts of warm water, stirred for 1 hour while being heated to 70 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. all day and night. 98 parts of a colorant (VB-1) were obtained. The average primary particle size was 31.2 nm.
  • Green pigment dispersion (V-DG-1) Green pigment dispersion (V-DG-1)
  • Eiger mill Mini Model M-250 MKII manufactured by Eiger Japan
  • zirconia beads having a diameter of 0.5 mm.
  • a green pigment dispersion (V-DG-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Example V-1 Green photosensitive coloring composition (V-RG-1)) A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1.0 ⁇ m filter to obtain a green photosensitive coloring composition (V-RG-1). Green pigment dispersion (V-DG-1) 55.0 parts Acrylic resin solution V-2 8.4 parts Photopolymerizable monomer (“Aronix M402” manufactured by Toagosei Co., Ltd.) 3.8 parts Photopolymerization initiator A (“Irgacure 379” manufactured by Ciba Japan Co., Ltd.) 1.9 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.3 parts Antioxidant A 0.16 parts Pentaerythritol tetrakis [3- ( 3,5-di-tert-butyl-4-hydroxyphenyl) propionate propylene glycol monomethyl ether acetate 20.44 parts cyclohexanone 10.0 parts
  • Examples V-2 to V-8 and Reference Examples V-1 to V-2 Green photosensitive coloring composition (V-RG-2 to 10)) With the composition and blending amount (parts by weight) shown in Table V-1, the pigment dispersion, the acrylic resin solution, the antioxidant, the photopolymerization initiator, the sensitizer, and the photopolymerizable monomer After stirring and mixing the mixture of the organic solvent and the organic solvent uniformly, the mixture was filtered through a 1 ⁇ m filter to obtain each photosensitive coloring composition.
  • Photopolymerizable monomer Dipentaerythritol hexaacrylate / pentaacrylate mixture (“Aronix M402” manufactured by Toagosei Co., Ltd.)
  • Photopolymerization initiator A 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (“Irga” manufactured by Ciba Japan) Cure 379 ”)
  • Photopolymerization initiator B Ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (0-acetyloxime) ("Irgacure OXE02" manufactured by Ciba Japan)
  • Sensitizer 4,4′-diethylaminobenzophenone (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) Anti
  • the obtained green photosensitive coloring composition was evaluated by the following methods for brightness, sensitivity, heat resistance, light resistance and voltage holding ratio. The results are shown in Table V-2.
  • the green photosensitive coloring composition (V-RG-1 to 10) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater and then dried at 70 ° C. for 20 minutes. Using a high pressure mercury lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. to obtain a coated substrate. Then, after heating at 220 ° C. for 30 minutes and allowing to cool, the brightness Y (C) of the obtained coated substrate was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.).
  • OSP-SP100 microspectrophotometer
  • the alkali developer was 1.5% by weight of sodium carbonate, 0.5% by weight of sodium hydrogen carbonate, 8.0% by weight of an anionic surfactant (“Perex NBL” manufactured by Kao Corporation), and 90% by weight of water. The thing which consists of was used.
  • the obtained green photosensitive coloring composition (V-RG-1 to 10) was applied to a 10 cm ⁇ 10 cm glass substrate by spin coating, and then heated at 70 ° C. for 15 minutes in a clean oven to remove the solvent. Thus, a coating film having a thickness of about 2 ⁇ m was obtained. Next, the substrate was cooled to room temperature, and then exposed to ultraviolet rays through a photomask having a stripe pattern of 100 ⁇ m width (pitch 200 ⁇ m) and 25 ⁇ m width (pitch 50 ⁇ m) using an ultrahigh pressure mercury lamp.
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 230 ° C. for 30 minutes in a clean oven.
  • the pattern film thickness in the 100 ⁇ m photomask portion of the filter segment formed by the above method was measured, and the minimum exposure amount that was 90% or more with respect to the film thickness after coating was evaluated.
  • the smaller the minimum exposure the higher the sensitivity and the better the photosensitive coloring composition.
  • the rank of evaluation is as follows. ⁇ : Less than 50 mJ / cm 2 ⁇ : 50 mJ / cm 2 or more and less than 100 mJ / cm 2 ⁇ : 100 mJ / cm 2 or more
  • the green photosensitive coloring composition (V-RG-1 to 10) was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick glass substrate using a spin coater and then dried at 70 ° C. for 20 minutes. Using a high-pressure mercury lamp, UV exposure was performed with an integrated light amount of 150 mJ / cm 2 and development was performed with an alkaline developer at 23 ° C. Subsequently, it heated at 220 degreeC for 30 minute (s), and after standing to cool, the coating-film board
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 230 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ⁇ Eab * was determined and evaluated in the following three stages.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 ) ⁇ : ⁇ Eab * is less than 5.0 ⁇ : ⁇ Eab * is 5.0 or more and less than 10.0 ⁇ : ⁇ Eab * is 10.0 or more
  • a coated substrate is prepared in the same manner as in the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) with a C light source is measured with a microspectrophotometer ( Measurement was performed using “OSP-SP100” manufactured by Olympus Optical Co., Ltd.
  • an ultraviolet cut filter (“COLORED OPTICAL GLASS L38” manufactured by Hoya Co., Ltd.) is attached on the substrate, and irradiated with ultraviolet rays for 100 hours using a 470 W / m 2 xenon lamp, then the chromaticity ([[ L * (2), a * (2), b * (2)]) was measured, and the color difference ⁇ Eab * was determined by the above formula and evaluated according to the same criteria as for heat resistance.
  • two glass substrates having an ITO transparent electrode with an effective electrode size of 10 mm ⁇ 10 mm are arranged facing each other so that the ITO transparent electrode surfaces face each other, and a small cell is produced using a sealing agent so that the cell gap is 9 ⁇ m. did.
  • a resist extraction liquid crystal sample solution is injected into the small cell between the cell gaps, a voltage of 5 V is applied at 60 ° C. for 60 ⁇ sec, and the cell voltage [V1] after the passage of 16.67 msec after the voltage is released Measured with a VHR-1S manufactured by Technica. The measurement was repeated 5 times, and the measured cell voltages were averaged.
  • Voltage holding ratio (%) ([V1] / 5) ⁇ 100 ⁇ : 95% or more ⁇ : 90% or more and less than 95% ⁇ : less than 90%
  • the filter segment formed using the photosensitive coloring composition containing the phthalocyanine dye represented by the formula (1) and the antioxidant has excellent brightness, sensitivity, and heat resistance. Good results were shown in the properties, light resistance, and voltage holding ratio (Examples V-1 to V-8).
  • Reference Example V-1 when no antioxidant was used as in Reference Example V-1, the brightness was low and the heat resistance was poor. Further, Reference Example V-2 using CI Pigment Green 58 had a poor voltage holding ratio as compared with the Example.
  • red photosensitive coloring composition (V-RR-1)) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a red pigment dispersion (V-DR-1) was prepared by filtration through a 0.0 ⁇ m filter. Red pigment (CI Pigment Red 254) 9.6 parts Red pigment (CI Pigment Red 177) 2.4 parts Resin-type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution V-1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • V-RR-1 red photosensitive coloring composition
  • Red pigment dispersion (V-DR-1) 42.0 parts Acrylic resin solution V-2 13.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts
  • Photopolymerization initiator Ciba Japan "Irgacure 907" 2.0 parts
  • Sensitizer Hodogaya Chemical "EAB-F"
  • V-RB-1 blue photosensitive coloring composition
  • Blue pigment dispersion (V-DB-1) 34.0 parts Acrylic resin solution
  • V-2 15.2 parts
  • Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.)
  • Photopolymerization initiator “Irgacure 907” manufactured by Ciba Japan Co., Ltd.) 2.0 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • the film was irradiated with ultraviolet rays of 150 mJ / cm 2 through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 220 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • V-RG-6 green photosensitive coloring composition
  • the measuring method of “number average molecular weight” and “weight average molecular weight” in the present example is the same as the measuring method in the example of Embodiment I.
  • Identification of aluminum phthalocyanine was determined by simultaneous quantitative analysis of carbon (C), hydrogen (H), and nitrogen (N) elements using Elemental Analysis 2400 manufactured by PerkinElmer.
  • the volume average primary particle size (MV) of aluminum phthalocyanine and the yellow colorant was determined by the transmission electron microscope (TEM) “H-7650” manufactured by Hitachi High-Technologies Corporation and the following calculation formula. First, colorant particles were photographed by TEM. In the obtained image, select 100 arbitrary colorant particles, the average value of the minor axis diameter and major axis diameter of the primary particles is the particle diameter (d) of the colorant particles, and then the individual colorants are selected. Considering the spheres having the obtained particle diameter (d), the volume (V) of each particle is obtained, and this operation is performed on 100 colorant particles, from which the calculation formula (VI-1) is used. did.
  • TEM transmission electron microscope
  • Example VI-1 Production of aluminum phthalocyanine (B) (VI-PB-1)
  • a reaction vessel 1000 parts of methanol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VI-1 and 43.1 parts of diphenylphosphinic acid were added up to 5 ° C. Cooled and allowed to react for 6 hours.
  • the reaction product was filtered, washed with 1800 parts of methanol and then with 1800 parts of water, and then dried under reduced pressure at 25 ° C. for 24 hours to obtain 116 parts of a blue product (phthalocyanine (A)).
  • phthalocyanine (B) (aluminum phthalocyanine (VI-PB-1)). Elemental analysis of the obtained phthalocyanine (B) revealed that the calculated value (C) 69.84%, (H) 3.46%, and (N) 14.81% were compared with the actually measured value (C) 69.
  • the aluminum phthalocyanine represented by the formula (12) was identified as 0.8%, (H) 3.5%, and (N) 14.8%.
  • Example VI-2 Production of aluminum phthalocyanine (VI-PB-2)
  • a reaction vessel 1000 parts of methanol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VI-1 and 43.1 parts of diphenylphosphinic acid were added and cooled to 5 ° C. The reaction was performed for 6 hours. The product was filtered, washed with 1800 parts of methanol and then with 1800 parts of water, and then dried under reduced pressure at 25 ° C. overnight to obtain 116 parts of a blue product (phthalocyanine (A)). After 116 parts of the obtained blue product was pulverized, the powder was placed in a heat-resistant container and heated in a thermostatic chamber at 230 ° C.
  • Example VI-3 Production of aluminum phthalocyanine (VI-PB-3) To a reaction vessel, 1000 parts of isopropyl alcohol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VI-1, and 43.1 parts of diphenylphosphinic acid were added and heated to 60 ° C. , Reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with 1800 parts of isopropyl alcohol and then with 1800 parts of water, and dried under reduced pressure at 25 ° C. overnight to give 112 parts of a blue product (phthalocyanine (A)). Got. 112 parts of the blue product obtained was added to 1120 parts of diethylene glycol and heated at 230 ° C. for 2 hours.
  • phthalocyanine (A) phthalocyanine
  • Example VI-4 Preparation of phthalocyanine (VI-PB-4) To a reaction vessel, 1000 parts of isopropyl alcohol, 100 parts of hydroxyaluminum phthalocyanine obtained in Preparation Example VI-1, and 43.1 parts of diphenylphosphinic acid were added and heated to 60 ° C. The reaction was allowed for 8 hours. After cooling to room temperature, the product was filtered, washed with 1800 parts of isopropyl alcohol and then with 1800 parts of water, and dried under reduced pressure at 25 ° C. overnight to give 112 parts of a blue product (phthalocyanine (A)). Got.
  • Example VI-5 Preparation of phthalocyanine (VI-PB-5) To a reaction vessel was added 1000 parts of dimethylformamide, 100 parts of hydroxyaluminum phthalocyanine obtained in Preparation Example VI-1, and 43.1 parts of diphenylphosphinic acid, and the mixture was heated to 70 ° C. The reaction was allowed for 8 hours. After cooling this to room temperature, the product was filtered, washed with 1800 parts of dimethylformamide and then with 1800 parts of water, filtered, and the resulting wet cake was dried at 80 ° C. overnight to give 108 parts of phthalocyanine (B) ( Aluminum phthalocyanine (VI-PG-5)) was obtained. Elemental analysis was performed on the obtained aluminum phthalocyanine.
  • B Aluminum phthalocyanine (VI-PG-5)
  • Example VI-6 Production of phthalocyanine (VI-PB-6) To a reaction vessel, 1000 parts of methanol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VI-1 and 43.1 parts of diphenylphosphinic acid were added, and the mixture was cooled to 5 ° C. Reacted for hours. The product was filtered, washed with 1800 parts of methanol and then with 1800 parts of water, and then dried at 25 ° C. under reduced pressure for 24 hours to obtain 116 parts of phthalocyanine (A) (aluminum phthalocyanine (VI-PB-6)). It was. Elemental analysis was performed on the obtained aluminum phthalocyanine.
  • Example VI-7 Production of aluminum phthalocyanine (VI-PB-7) To a reaction vessel was added 1000 parts of isopropyl alcohol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VI-1, and 43.1 parts of diphenylphosphinic acid, and the mixture was heated to 60 ° C. , Reacted for 8 hours. After cooling to room temperature, the product was filtered, washed with 1800 parts of isopropyl alcohol and then with 1800 parts of water, and then dried under reduced pressure at 25 ° C. overnight to give 112 parts of phthalocyanine (A) (aluminum phthalocyanine (VI -PB-7)) was obtained.
  • A aluminum phthalocyanine (VI -PB-7)
  • the measured value (C) 69.8 was calculated against the calculated value (C) 69.84%, (H) 3.46%, and (N) 14.81%. %, (H) 3.6%, (N) 14.9%, and it was confirmed that this was an aluminum phthalocyanine represented by the formula (12). Moreover, the volume average primary particle diameter was 33 nm. Further, when an X-ray diffraction pattern by CuK ⁇ ray was measured, as shown in FIG.
  • Example VI-8 Production of aluminum phthalocyanine (VI-PB-8)
  • 1000 parts of dimethylformamide, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VI-1, and 43.1 parts of diphenylphosphinic acid were added and heated to 70 ° C. , Reacted for 8 hours.
  • the product was filtered, washed with 1800 parts of dimethylformamide and then with 1800 parts of water, and dried under reduced pressure at 25 ° C. overnight to give 108 parts of phthalocyanine (A) (aluminum phthalocyanine (VI -PB-8)) was obtained. Elemental analysis was performed on the obtained aluminum phthalocyanine.
  • the mixture was further heated and stirred at 80 ° C. for 3 hours to obtain a binder resin solution.
  • binder resin solution After cooling to room temperature, about 2 g of binder resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and PGMAC was added so that the nonvolatile content was 20% by weight to prepare a sample solution. .
  • Mw weight average molecular weight
  • Example VI-9 Production of Blue Colored Composition (VI-DB-1) After stirring and mixing a mixture having the following composition uniformly, Eiger Mill (Eiger Japan Co., Ltd.) was used as a media type wet disperser using zirconia beads having a diameter of 0.5 mm. For 4 hours to produce a blue colored composition (VI-DB-1) having a pigment content of 50% and a solid content of 20%.
  • Eiger Mill Eiger Japan Co., Ltd.
  • a blue colored composition VI-DB-1 having a pigment content of 50% and a solid content of 20%.
  • Aluminum phthalocyanine (VI-PB-1) 10.0 parts
  • Resin type dispersant (“BYK-LPN6919” manufactured by Big Chemie) 8.3 parts
  • a coated substrate giving the chromaticities shown in Table VI-1 was obtained.
  • Example VI-10 to 22, Reference Example VI-2 Production of blue colored composition (VI-DB-2 to VI-DB-15) A blue colored composition (VI-) was prepared in the same manner as in Example VI-9, except that the composition was changed as shown in Table VI-1. DB-2 to VI-DB-15) were prepared.
  • the manufacturing method of the coloring composition (green coloring composition) containing a yellow coloring agent is shown.
  • the manufacturing method of the yellow coloring agent used by manufacture of a green coloring composition and the manufacturing method of the coloring composition (yellow coloring composition) which consists of a yellow coloring agent are shown.
  • ⁇ Foreign matter evaluation> The evaluation of the generation of foreign matter was performed by applying a colored composition on a transparent substrate so that the dried coating film was about 2.0 ⁇ m, and performing a heat treatment at 230 ° C. for 1 hour in an oven. The number of foreign objects was counted. The evaluation was carried out using a Olympus system metal microscope “BX60”). The magnification was set to 500 times, and the number of foreign matters observable in arbitrary five fields of view through transmission was measured.
  • ⁇ and ⁇ are good with a small number of foreign matters, ⁇ is a level where there is a large number of foreign matters, but there is no problem in use, and ⁇ is a coating unevenness (splots) due to foreign matters, so it cannot be used practically Corresponds to the state.
  • ⁇ Number of foreign matter is less than 5 ⁇ : Number of foreign matter is 5 or more, less than 20 ⁇ : Number of foreign matter is 21 or more, less than 100 ⁇ : Number of foreign matter is 100 or more
  • Table VI-3 and Table VI-4 show the results of the blue and green colored compositions prepared in Examples and Reference Examples.
  • the blue coloring composition using aluminum phthalocyanine represented by the formula (12) is compared with the blue coloring composition using hydroxyaluminum phthalocyanine (Reference Example VI-2).
  • the color difference of heat resistance and light resistance evaluation was small, and good results were obtained.
  • the blue coloring composition using phthalocyanine (B) (Examples VI-9 to VI-16) is compared with the blue coloring composition using phthalocyanine (A) (Examples VI-17 to VI-22). Further, the color difference between the heat resistance and the light resistance was further reduced, and the results were satisfactory.
  • Example VI-12 in which the resin type dispersant was not added, and Compared with the blue coloring composition of Example VI-20, the foreign matter evaluation gave a good result.
  • the green coloring composition using the aluminum phthalocyanine represented by the formula (12) and the yellow coloring agent has a small color difference in the heat resistance and light resistance evaluation, and is excellent in the foreign matter evaluation. It became a result.
  • the prepared coated substrate was made to have chromaticity with a C light source shown in Table VI-5 after heat treatment at 230 ° C.
  • Examples VI-9 to VI- were prepared using the above substrates prepared using the photosensitive coloring compositions obtained in Examples VI-37 to VI-44 and Reference Examples VI-5 to VI-7. 27. The same evaluation as in Reference Examples VI-1 to VI-3 was performed.
  • Examples VI-9 to VI- were prepared using the above substrates prepared using the photosensitive coloring compositions obtained in Examples VI-37 to VI-44 and Reference Examples VI-5 to VI-7. 27. The same evaluation as in Reference Examples VI-2 to VI-4 was performed.
  • Table VI-6 shows the results of the photosensitive coloring compositions produced in Examples and Reference Examples.
  • the photosensitive coloring composition using the aluminum phthalocyanine represented by the formula (12) is the same as the coloring composition shown in Examples VI-9 to VI-36.
  • the photosensitive coloring composition containing hydroxyaluminum phthalocyanine generally resulted in poor heat resistance and light resistance.
  • Example VI- No. 39, VI-41 and Reference Example VI-6, Examples VI-42, VI-44 and Reference Example VI-7 the coloring composition containing aluminum phthalocyanine represented by the formula (12): Compared with the coloring composition containing hydroxyaluminum phthalocyanine, the result showed high brightness.
  • a black matrix is patterned on a glass substrate, and aluminum phthalocyanine used in the photosensitive coloring composition (VI-RB-1) is formed on the substrate by a spin coater.
  • the film was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • the color filter was obtained by applying the film to such a film thickness to form a blue filter segment.
  • Example VII-1 Production of aluminum phthalocyanine (VII-PB-1) To a reaction vessel, 2000 parts of N, N-dimethylformamide, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1, and 53.9 parts of diphenyl phosphate were added. After reacting at 85 ° C. for 3 hours, this solution was poured into 12000 parts of water. The reaction product was filtered, washed with 24,000 parts of water, and dried overnight at 60 ° C. under reduced pressure to obtain 123 parts of a blue product (phthalocyanine (C)).
  • phthalocyanine (D) (aluminum phthalocyanine (VII-PB-1)). Obtained. Elemental analysis of the obtained phthalocyanine (D) revealed that the calculated value (C) 67.01%, (H) 3.32%, (N) 14.21%, and the actual value (C) 66 9.9%, (H) 3.3%, and (N) 14.1%, and the aluminum phthalocyanine represented by the formula (13) was identified. Moreover, the volume average primary particle diameter was 31 nm.
  • Example VII-2 Production of aluminum phthalocyanine (VII-PB-2) To a reaction vessel, 2000 parts of N, N-dimethylformamide, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1, and 53.9 parts of diphenyl phosphate were added. After reacting at 85 ° C. for 3 hours, this solution was poured into 12000 parts of water. The reaction product was filtered, washed with 24,000 parts of water, and dried overnight at 60 ° C. under reduced pressure to obtain 123 parts of a blue product (phthalocyanine (C)). 123 parts of the blue product obtained was added to 1230 parts of PGMAC and heated at 145 ° C. for 2 hours.
  • phthalocyanine (C) 123 parts of the blue product obtained was added to 1230 parts of PGMAC and heated at 145 ° C. for 2 hours.
  • Example VII-3 Production of aluminum phthalocyanine (VII-PB-3)
  • a reaction vessel 1200 parts of methanol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1 and 53.9 parts of diphenyl phosphate were added and cooled to 5 ° C. The reaction was performed for 6 hours. The product was filtered, washed with 1800 parts of methanol and then with 1800 parts of water, and then dried under reduced pressure at 60 ° C. overnight to obtain 120 parts of a blue product (phthalocyanine (C)). After pulverizing 120 parts of the resulting blue product, the powder was placed in a heat-resistant container and heated in a thermostatic chamber at 180 ° C.
  • Example VII-4 Production of aluminum phthalocyanine (VII-PB-4)
  • a reaction vessel 1200 parts of methanol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1 and 53.9 parts of diphenyl phosphate were added and cooled to 5 ° C. The reaction was performed for 6 hours. The product was filtered, washed with 1800 parts of methanol and then with 1800 parts of water, and then dried under reduced pressure at 60 ° C. overnight to obtain 120 parts of a blue product (phthalocyanine (C)). 120 parts of the blue product obtained was added to 1200 parts of xylene and heated at 135 ° C. for 2 hours.
  • phthalocyanine (C) phthalocyanine
  • Example VII-5 Production of aluminum phthalocyanine (VII-PB-5)
  • a reaction vessel 2000 parts of dimethyl sulfoxide, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1, and 53.9 parts of diphenyl phosphate were added and heated to 110 ° C. After reacting for 5 hours, this solution was poured into 12000 parts of water. The reaction product was filtered, washed with 24,000 parts of water, and dried overnight at 60 ° C. under reduced pressure to obtain 125 parts of a blue product (phthalocyanine (C)). After pulverizing 125 parts of the obtained blue product, the powder was put in a heat-resistant container and heated in a thermostatic chamber at 200 ° C.
  • Example VII-6 Production of aluminum phthalocyanine (VII-PB-6) 2000 parts of N, N-dimethylformamide, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1, and 53.9 parts of diphenyl phosphate were added. After reacting at 85 ° C. for 3 hours, this solution was poured into 12000 parts of water. The reaction product was filtered, washed with 24,000 parts of water, and dried overnight at 60 ° C. under reduced pressure to obtain 123 parts of aluminum phthalocyanine (C) (aluminum phthalocyanine (VII-PB-6)).
  • C aluminum phthalocyanine
  • Example VII-7 Production of aluminum phthalocyanine (VII-PB-7)
  • a reaction vessel 1200 parts of methanol, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1 and 53.9 parts of diphenyl phosphate were added and cooled to 5 ° C. The reaction was performed for 6 hours. The product was filtered, washed with 1800 parts of methanol and then with 1800 parts of water, and then dried under reduced pressure at 60 ° C. overnight to obtain 120 parts of phthalocyanine (C) (aluminum phthalocyanine (VII-PB-7)). It was.
  • Example VII-8 Production of aluminum phthalocyanine (VII-PB-8) To a reaction vessel was added 2000 parts of dimethyl sulfoxide, 100 parts of hydroxyaluminum phthalocyanine obtained in Production Example VII-1, and 53.9 parts of diphenyl phosphate, and the mixture was heated to 110 ° C. After reacting for 5 hours, this solution was poured into 12000 parts of water. The reaction product was filtered, washed with 24,000 parts of water, and dried overnight at 60 ° C. under reduced pressure to obtain 125 parts of phthalocyanine (C) (aluminum phthalocyanine (VII-PB-8)).
  • C aluminum phthalocyanine
  • the mixture was further heated and stirred at 80 ° C. for 3 hours to obtain a binder resin solution.
  • binder resin solution After cooling to room temperature, about 2 g of binder resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and PGMAC was added so that the nonvolatile content was 20% by weight to prepare a sample solution. .
  • Mw weight average molecular weight
  • Example VII-9 Production of Blue Colored Composition (VII-DB-1) After stirring and mixing a mixture having the following composition uniformly, Eiger Mill (Eiger Japan Co., Ltd.) was used as a media type wet disperser using zirconia beads having a diameter of 0.5 mm. The product was dispersed for 4 hours using a “Mini Model M-250 MKII” manufactured by the manufacturer, thereby producing a blue coloring composition (VII-DB-1) having a pigment content of 50% and a solid content of 20%.
  • Aluminum phthalocyanine (VII-PB-1) 10.0 parts Resin-type dispersant ("BYK-LPN6919" manufactured by Big Chemie) 8.3 parts Binder resin solution 25.0 parts PGMAC 56.7 parts
  • a coated substrate giving the chromaticity shown in Table VII-1 was obtained.
  • Example VII-10 to VII-22 Reference Example VII-2
  • DB-2 to VII-DB-15) were prepared.
  • the manufacturing method of the coloring composition (green coloring composition) containing a yellow coloring agent is shown.
  • the manufacturing method of the yellow coloring agent used by manufacture of a green coloring composition and the manufacturing method of the coloring composition (yellow coloring composition) which consists of a yellow coloring agent are shown.
  • ⁇ Foreign matter evaluation> The evaluation of the generation of foreign matter was performed by applying a colored composition on a transparent substrate so that the dried coating film was about 2.0 ⁇ m, and performing a heat treatment at 230 ° C. for 1 hour in an oven. The number of foreign objects was counted. The evaluation was carried out using a Olympus system metal microscope “BX60”). The magnification was set to 500 times, and the number of foreign matters observable in arbitrary five fields of view through transmission was measured.
  • ⁇ and ⁇ are good with a small number of foreign matters, ⁇ is a level where there is a large number of foreign matters, but there is no problem in use, and ⁇ is a coating unevenness (splots) due to foreign matters, so it cannot be used practically Corresponds to the state.
  • ⁇ Number of foreign matter is less than 5 ⁇ : Number of foreign matter is 5 or more, less than 20 ⁇ : Number of foreign matter is 21 or more, less than 100 ⁇ : Number of foreign matter is 100 or more
  • Table VII-3 and Table VII-4 show the results of the blue and green colored compositions prepared in Examples and Reference Examples.
  • the blue coloring composition using aluminum phthalocyanine represented by the formula (13) is compared with the blue coloring composition using hydroxyaluminum phthalocyanine (Reference Example VII-2).
  • the color difference of heat resistance and light resistance evaluation was small, and good results were obtained.
  • the blue coloring composition using phthalocyanine (D) (Examples VII-9 to VII-16) is compared with the blue coloring composition using phthalocyanine (C) (Examples VII-17 to VII-22). Further, the color difference between the heat resistance and the light resistance was further reduced, and the results were satisfactory.
  • Examples VII-9 to 11, 13 to 19, and 21 to 22 by adding a resin type dispersant, Examples VII-12 and Example VII to which no resin type dispersant was added were added. Compared with the blue coloring composition of ⁇ 20, the foreign matter evaluation gave a good result.
  • the green coloring composition using the aluminum phthalocyanine represented by the formula (13) and the yellow coloring agent has a small color difference in heat resistance and light resistance evaluation, and is good in foreign matter evaluation. It became a result.
  • Example VII-38, Reference Example VII-5 Preparation of photosensitive coloring composition (VII-RB-2, 3) Photosensitive coloring composition (VII-RB-2, 3) was prepared in the same manner as in Example VII-37 except that the composition was changed to the composition shown in Table VII-5. 3) was produced.
  • the prepared coated substrate was made to have the chromaticity with the C light source shown in Table VII-5 after heat treatment at 230 ° C.
  • Table VII-6 shows the results of the photosensitive coloring compositions produced in Examples and Reference Examples.
  • the photosensitive coloring composition using the aluminum phthalocyanine represented by the formula (13) is the same as the coloring composition shown in Examples VII-9 to VII-36.
  • the photosensitive coloring composition containing hydroxyaluminum phthalocyanine generally resulted in poor heat resistance and light resistance.
  • Example VII- 39, VII-41 and Reference Example 6, Examples VII-42, VII-44, and Reference Example VII-7 the coloring composition containing aluminum phthalocyanine represented by the formula (13) was obtained by using hydroxyaluminum. Compared with the coloring composition containing phthalocyanine, the result showed high brightness.
  • a black matrix is patterned on a glass substrate, and the aluminum phthalocyanine used in the photosensitive coloring composition (VII-RB-1) is spin-coated on the substrate.
  • the film was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • the color filter was obtained by applying the film to such a film thickness to form a blue filter segment.

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Abstract

La présente invention concerne une composition colorée pour filtres colorés, qui comporte un agent colorant, une résine liante et un solvant organique, l'agent colorant comportant un composé de phtalocyanine représenté par la formule (1) dans laquelle: X1-X4 et Yl-Y4 représentent indépendamment un substituant; M représente Al; Z représente -OP(=O)R1R2; et m1, m2, m3, m4, n1, n2, n3 et n4 représentent indépendamment un nombre entier de 0 à 4.
PCT/JP2012/051881 2011-01-28 2012-01-27 Composition colorée pour filtres colorés, et filtre coloré Ceased WO2012102395A1 (fr)

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JP2011-118728 2011-05-27
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JP2011219021A JP5764805B2 (ja) 2011-10-03 2011-10-03 アルミニウムフタロシアニン
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JP7196595B2 (ja) 2018-12-26 2022-12-27 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、およびカラーフィルタ
WO2020241535A1 (fr) 2019-05-31 2020-12-03 富士フイルム株式会社 Capteur optique et dispositif de détection
WO2021039205A1 (fr) 2019-08-29 2021-03-04 富士フイルム株式会社 Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé
JP7363204B2 (ja) 2019-08-29 2023-10-18 東洋インキＳｃホールディングス株式会社 フタロシアニン顔料、着色組成物およびカラーフィルター
JP2021031652A (ja) * 2019-08-29 2021-03-01 東洋インキＳｃホールディングス株式会社 フタロシアニン顔料、着色組成物およびカラーフィルター
WO2021039253A1 (fr) 2019-08-30 2021-03-04 富士フイルム株式会社 Composition, film, filtre optique et procédé de production associé, élément d'imagerie à semi-conducteurs, capteur infrarouge et module de capteur
JPWO2022054612A1 (fr) * 2020-09-08 2022-03-17
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2023234096A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de détection de lumière, capteur d'image et procédé de production d'élément de détection de lumière
WO2023234095A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément de photodétection, capteur d'image et procédé de fabrication d'élément de photodétection
WO2023234094A1 (fr) 2022-06-01 2023-12-07 富士フイルム株式会社 Élément photodétecteur, capteur d'image et procédé de fabrication d'élément photodétecteur
WO2024154721A1 (fr) * 2023-01-20 2024-07-25 住友化学株式会社 Composition de résine durcissable colorée
WO2024154720A1 (fr) * 2023-01-20 2024-07-25 住友化学株式会社 Composition de résine durcissable colorée

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TWI512053B (zh) 2015-12-11
CN103370642B (zh) 2015-07-15
CN103370642A (zh) 2013-10-23

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