Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2/00—Processes of polymerisation
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
  • C08K5/098—Metal salts of carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• • 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
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/04—Isoindoline dyes
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/0005—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
• • 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 colored curable resin composition, a color filter, and a display device.
• Colored curable resin compositions are used in the manufacture of color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays.
• the colored curable resin composition may contain two or more colorants having different colors in order to obtain a desired color tone or the like.
• Patent Document 1 JP-A-2017-186546 (Patent Document 1) describes a colored curable resin composition containing a phthalocyanine-based colorant, a yellow colorant, and a metal compound (M).
• the present invention relates to a colored curable resin composition capable of forming a color filter having a small degree of lightness reduction even if it contains a metal compound, a color filter formed from the colored curable resin composition, and the color It is to provide a display device including a filter.
• the present invention provides the following colored curable resin composition, color filter, and display device.
• Metal salt (A) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group, a colorant (B) containing a phthalocyanine colorant and a yellow colorant, resin (C), polymerization A colored curable resin composition comprising a functional compound (D) and a polymerization initiator (E).
• a colored curable resin composition according to [1] wherein the carbon number is 10 to 36.
• a display device including the color filter according to [3].
• the colored curable resin composition of the present invention it is possible to provide a color filter having a small degree of lightness reduction even if it contains a metal compound, and a display device including the color filter.
• the colored curable resin composition of the present invention comprises a metal salt (A) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group, a colorant (B) containing a phthalocyanine colorant and a yellow colorant. ), Resin (C), polymerizable compound (D), and polymerization initiator (E). According to the said colored curable resin composition, even if it contains a metal compound, a cured film (color filter etc.) with a small degree of brightness reduction can be formed.
• the metal salt (A) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group is also referred to as “aliphatic carboxylic acid metal salt (A)”.
• the compound illustrated as each component in this specification can be used individually or in combination of multiple types.
• Aliphatic carboxylic acid metal salt (A) By including the aliphatic carboxylic acid metal salt (A), the colored curable resin composition of the present invention forms a cured film (color filter or the like) having a small degree of lightness reduction even if it contains a metal compound. Can do.
• the aliphatic carboxylic acid metal salt (A) is a salt composed of a metal cation and an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group.
• the aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group is also referred to as “aliphatic carboxylic acid (X)”.
• aliphatic carboxylic acid means a carboxylic acid having no aromatic ring.
• the colored curable resin composition of the present invention may contain only one type of aliphatic carboxylic acid metal salt (A), or may contain two or more types.
• the aliphatic carboxylic acid (X) has 1 to 40 carbon atoms including carbon of the carboxy group, and may be linear, branched or cyclic. It may be a combination of two or more structures selected from the group consisting of a linear structure, a branched chain structure and a cyclic structure.
• the aliphatic carboxylic acid (X) may contain an unsaturated bond.
• the aliphatic carboxylic acid (X) has one or more hydroxy groups in the molecule.
• the aliphatic carboxylic acid (X) has one or more carboxy groups in the molecule.
• the number of carboxy groups is usually 10 or less.
• the number of carbon atoms of the aliphatic carboxylic acid (X) is 1 to 40, preferably 10 to 36, from the viewpoint of reducing the degree of lightness reduction even if the cured film (color filter or the like) contains a metal compound. Yes, more preferably 12-24.
• the aliphatic carboxylic acid metal salt (A) may have at least one anion of the aliphatic carboxylic acid (X).
• the aliphatic carboxylic acid metal salt (A) has two or more kinds of anions of the aliphatic carboxylic acid (X). It may have an anion of aliphatic carboxylic acid (X) and an anion other than the anion of aliphatic carboxylic acid (X).
• the other anion is not particularly limited and may be a halogen ion, a nitrate ion, a sulfate ion, or the like, but is preferably an anion of an aliphatic carboxylic acid other than the aliphatic carboxylic acid (X).
• the aliphatic carboxylic acid other than the aliphatic carboxylic acid (X) means an aliphatic carboxylic acid having no hydroxy group.
• the aliphatic carboxylic acid (X) is the same as the aliphatic carboxylic acid (X) except having no hydroxy group.
• the anion contained in the aliphatic carboxylic acid metal salt (A) is preferably composed only of the anion of the aliphatic carboxylic acid (X).
• the metal cation of the aliphatic carboxylic acid metal salt (A) is preferably a metal cation having a valence of 2 or more and a valence of 10 or less from the viewpoint of improving the light resistance of the cured film (color filter or the like).
• Examples of the bivalent or higher metal cation include cations of metals belonging to Groups 2 to 15 of the periodic table of elements.
• the metal cation is preferably a divalent to hexavalent metal cation.
• Metal cations are More preferably, divalent such as Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Cd 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Hg 2+ , Fe 2+ , Co 2+ , Sn 2+ , Pb 2+ and Mn 2+.
• the aliphatic carboxylic acid metal salt (A) may be a compound represented by the following formula (Aa).
• D represents an aliphatic hydrocarbon having a hydroxy group.
• a represents an integer of 1 to 10, and preferably an integer of 1 to 3. When a plurality are present, they may be the same as or different from each other.
• the carbon number + a of D is an integer of 1 to 40.
• b represents any integer of 1 or more. When b represents any integer of 2 or more, “[D]-(CO 2 ⁇ ) a ” may be the same as or different from each other.
• J k- represents an anion other than “[D]-(CO 2 ⁇ ) a ”.
• k represents an integer of 1 to 10, preferably an integer of 1 to 6.
• m represents any integer of 0 or more.
• a c + represents a c-valent metal cation, and specific examples thereof are as described above.
• c represents an integer of 2 to 10, preferably an integer of 2 to 6.
• d represents any integer of 1 or more.
• a c + may be the same as or different from each other.
• the total valence of Is equal to the valence of. ]
• the aliphatic carboxylic acid metal salt (A) is obtained, for example, as a precipitate generated by dissolving the aliphatic carboxylic acid (X) in an alkaline aqueous solution and then adding a salt having a metal cation (such as a halide). be able to.
• the obtained aliphatic carboxylic acid metal salt (A) may be subjected to purification treatment such as washing, if necessary.
• the content of the aliphatic carboxylic acid metal salt (A) is based on the total solid content of the colored curable resin composition. Preferably they are 0.01 mass% or more and 60 mass% or less, More preferably, it is 0.1 mass% or more and 50 mass% or less, More preferably, it is 0.5 mass% or more and 40 mass% or less, Especially preferably, it is 0.5 to 30 mass%.
• the content of the aliphatic carboxylic acid metal salt (A) is within the above range, a decrease in brightness can be significantly suppressed even if the cured film (color filter or the like) contains a metal compound.
• total amount of solids means an amount obtained by removing the content of the solvent from the total amount of the colored curable resin composition.
• the total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.
• the content of the aliphatic carboxylic acid metal salt (A) is 100 parts by mass of the total amount of the phthalocyanine colorant and the yellow colorant, Preferably it is 0.01 parts by weight or more and 100 parts by weight or less, More preferably, it is 0.1 to 80 parts by mass, More preferably, it is 0.5 to 50 parts by mass, Especially preferably, it is 0.5 to 40 mass parts.
• M, L, p and q are each a compound represented by the following [Table A], [ in the compounds AA1 ⁇ AA22 Table a], Mg 2+ instead of M is Fe 2+, Ca 2+, Sr 2+ , Ba 2+, Cd 2+, Ni 2+, Zn 2+, Cu 2+, Hg 2+, Co 2+, Sn 2+, A compound represented by Pb 2+ or Mn 2+ , a compound represented by [Table B], a compound AA23 to AA44 of [Table B], wherein M is Al 3+ , Co 3+ or Cr 3+ instead of Fe 3+ , And compounds represented by [Table C].
• Examples of the aliphatic carboxylic acid metal salt (A) having an anion of the aliphatic carboxylic acid (X) and an anion other than the anion of the aliphatic carboxylic acid (X) include, for example, a salt represented by the following formula: Is mentioned.
• the colorant (B) includes a phthalocyanine colorant and a yellow colorant.
• the phthalocyanine colorant is preferably a halogenated phthalocyanine colorant, and may be a pigment, a dye, or may contain both a pigment and a dye.
• phthalocyanine pigment examples include halogenated phthalocyanine pigments and non-halogenated phthalocyanine pigments. These phthalocyanine pigments may contain a metal atom such as a copper atom, a zinc atom, or an aluminum atom.
• halogenated phthalocyanine pigments include halogenated copper phthalocyanine pigments such as fluorinated copper phthalocyanine pigment, chlorinated copper phthalocyanine pigment, brominated copper phthalocyanine pigment; fluorinated zinc phthalocyanine pigment, chlorinated zinc phthalocyanine pigment, brominated Halogenated zinc phthalocyanine pigments such as zinc phthalocyanine pigments; Halogenated aluminum phthalocyanine pigments such as fluorinated aluminum phthalocyanine pigments, chlorinated aluminum phthalocyanine pigments and brominated aluminum phthalocyanine pigments.
• halogenated copper phthalocyanine pigments such as fluorinated copper phthalocyanine pigment, chlorinated copper phthalocyanine pigment, brominated copper phthalocyanine pigment
• fluorinated zinc phthalocyanine pigment chlorinated zinc phthalocyanine pigment, brominated Halogenated zinc phthalocyanine pigments
• non-halogenated phthalocyanine pigment examples include copper phthalocyanine pigment, zinc phthalocyanine pigment, and aluminum phthalocyanine pigment.
• the colorant (B) preferably contains a phthalocyanine pigment, more preferably a halogenated phthalocyanine pigment.
• the phthalocyanine pigment is not particularly limited, and a known pigment can be used, and examples thereof include pigments classified as pigments by the color index (published by The Society of Dyers and Colorists).
• the phthalocyanine pigment examples include C.I. I. Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; C. I. And blue pigments such as CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16 and the like.
• the phthalocyanine pigment is preferably the above green pigment, more preferably C.I. I. Pigment green 7, C.I. I. Pigment green 58, C.I. I. Pigment green 59, C.I. I. Pigment green 62 and / or C.I. I. And CI Pigment Green 63.
• the phthalocyanine dye is not particularly limited, and a known dye can be used. Examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of the phthalocyanine dyes include known dyes described in Color Index (published by The Society of Dyers and Colorists) and dyeing notes (Color Dye Co.).
• phthalocyanine dyes examples include C.I. I. Solvent dyes such as Solvent Blue 38, 44, 67, 70; I. Direct dyes such as direct blue 86, 87, 189, 199; I. Modern dyes such as Modern Blue 77; C.I. I. Acid dyes such as Acid Blue 242, 243, 249 and the like.
• the yellow colorant may be a pigment, a dye, or may contain both a pigment and a dye.
• the yellow pigment is not particularly limited, and a known pigment can be used, and examples thereof include pigments classified as pigments according to a color index (published by The Society of Dyers and Colorists).
• yellow pigments include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231 and the like.
• the yellow dye is not particularly limited, and a known dye can be used, and examples thereof include a solvent dye, an acid dye, a direct dye, and a mordant dye.
• examples of the yellow dye include known dyes described in Color Index (published by The Society, of Dyers, and Colorists) and Dyeing Notes (Color Dyeing).
• yellow dyes include C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189, etc. . I. Solvent dyes; C. I.
• Acid Yellow 1 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251 and the like.
• Direct dyes C. I. Disperse Yellow 51, 54, 76 etc.
• Reactive dyes C. I. Modern Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65, etc. I. Examples include modern dyes.
• the colored curable resin composition preferably contains at least one yellow pigment as a yellow colorant, and more preferably contains a yellow pigment classified as a quinophthalone pigment or an isoindoline pigment.
• the yellow pigment is C.I. I. Pigment yellow 138, C.I. I. Quinophthalone pigments such as CI Pigment Yellow 231, and C.I. I.
• An isoindoline pigment such as CI Pigment Yellow 185 is preferable.
• the total content of the colorant (B) is based on the total solid content of the colored curable resin composition. Preferably they are 0.01 mass% or more and 90 mass% or less, More preferably, it is 1 mass% or more and 60 mass% or less, More preferably, it is 1 mass% or more and 50 mass% or less.
• the total content of the phthalocyanine colorant and the yellow colorant in the colorant (B) is as follows: Usually 100% by mass or less, Preferably they are 1 mass% or more and 100 mass% or less, More preferably, it is 10 mass% or more and 100 mass% or less, More preferably, it is 50 mass% or more and 100 mass% or less, Especially preferably, it is 70 mass% or more and 100 mass% or less.
• the content of the yellow colorant in the colorant (B) is based on the total amount of the phthalocyanine colorant and the yellow colorant. Preferably they are 0.01 mass% or more and 99.99 mass% or less, More preferably, it is 1 mass% or more and 80 mass% or less, More preferably, it is 3 mass% or more and 60 mass% or less.
• the colored curable resin composition may contain a colorant other than the phthalocyanine colorant and the yellow colorant in the colorant (B).
• the other colorant may be a pigment, a dye, or may contain both a pigment and a dye.
• Other colorants may be used alone or in combination of two or more.
• pigments known pigments can be used.
• pigments other than phthalocyanine pigments and yellow pigments among pigments classified as pigments in the color index can be used. Can be mentioned.
• pigments include C.I. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, Red pigments such as 268, 269, 273; C. I. Blue pigments other than phthalocyanine blue pigments such as CI Pigment Blue 60; C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; C. I. Brown pigments such as CI Pigment Brown 23 and 25; C. I. And black pigments such as CI Pigment Black 1 and 7.
• Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59,
• dyes known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes.
• examples of the dye include dyes other than phthalocyanine dyes and yellow dyes among known dyes described in Color Index (published by The Society of Dyers and Colorists) and Dyeing Notes (Color Dyeing). .
• dyes More specifically, as other dyes, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes Examples thereof include dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.
• dyes include C.I. I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C. I. Solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C. I.
• Solvent Blue 4 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. I. Solvent dyes, C. I.
• Acid dyes C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; C. I.
• Direct dyes C. I. Disperse violet 26, 27; C. I. Disperse Blue 1, 14, 56, 60, etc.
• I. Disperse dyes C. I. Basic Red 1, 10; C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C. I. Basic violet 2; C. I. Basic Red 9; C. I. C. such as Basic Green 1; I. Basic dyes, C.
• Resin (C) is preferably an alkali-soluble resin, and is at least one monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter, “(a)”. It is more preferable that the polymer has a structural unit derived from.
• Resin (C) is a structural unit derived from a monomer (b) having a C2-C4 cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”), And a copolymer having other structural units.
• the monomer (c) copolymerizable with the monomer (a) (however, different from the monomer (a) and the monomer (b).
• (c) And a structural unit having an ethylenically unsaturated bond, and the like.
• (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
• Examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-
• acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution.
• (B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
• (B) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
• Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), an oxetanyl group and an ethylenically unsaturated bond.
• Examples of (b1) include a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”) And a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-2)”).
• (B1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond.
• Examples of (b1-1) include glycidyl (meth) acrylate, ⁇ -methylglycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, and m-vinylbenzyl glycidyl ether.
• Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl ( (Meth) acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), Examples thereof include a compound represented by formula (I) and a compound represented by formula (II).
• R a and R b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group May be substituted.
• X a and X b are each independently a single bond, * - R c -, * - R c -O -, * - represents the R c -S- or * -R c -NH-.
• R c represents an alkanediyl group having 1 to 6 carbon atoms. * Represents a bond with O.
• alkyl group having 1 to 4 carbon atoms examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
• alkyl group in which a hydrogen atom is substituted with hydroxy examples include, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1 -Hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like can be mentioned.
• R a and R b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group or a 2-hydroxyethyl group, more preferably a hydrogen atom or a methyl group.
• alkanediyl group examples include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, Examples include hexane-1,6-diyl group.
• X a and X b are preferably a single bond, a methylene group, an ethylene group, * —CH 2 —O— and * —CH 2 CH 2 —O—, more preferably a single bond, * —CH 2. CH 2 —O— (* represents a bond with O).
• Examples of the compound represented by the formula (I) include compounds represented by any one of the formulas (I-1) to (I-15). Among them, formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) or formula (I-11) to formula (I-15) A compound represented by formula (I-1), formula (I-7), formula (I-9) or formula (I-15) is more preferred.
• Examples of the compound represented by the formula (II) include compounds represented by any one of the formulas (II-1) to (II-15). Among them, formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) or formula (II-11) to formula (II-15) A compound represented by formula (II-1), formula (II-7), formula (II-9) or formula (II-15) is more preferred.
• the compound represented by the formula (I) and the compound represented by the formula (II) may be used alone or in combination of two or more.
• the content ratio thereof [the compound represented by the formula (I): the compound represented by the formula (II)] is: On a molar basis, it is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, and still more preferably 20:80 to 80:20.
• (B2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group.
• Examples of (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, and 3-ethyl-3-acryloyloxy.
• Examples include methyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane. .
• (B3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group.
• Examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
• (B) is preferably (b1) in that the color filter obtained can have higher reliability such as heat resistance and chemical resistance. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.
• Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth).
• the resin (C) specifically, 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] Decyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid Copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 2, 6] decyl (meth) acrylate / (meth) acrylic acid / N- cyclohexyl male
• Resin (C) may combine 2 or more types, and in this case, resin (C) is at least, It is preferable to include at least one copolymer containing the structural unit derived from (a) and the structural unit derived from (b), More preferably, it contains at least one copolymer comprising the structural unit derived from (a) and the structural unit derived from (b1), More preferably, it contains at least one copolymer comprising the structural unit derived from (a) and the structural unit derived from (b1-2), 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2 , 6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexy
• the polystyrene equivalent weight average molecular weight (Mw) of the resin (C) is preferably 1,000 to 100,000, more preferably 1,000 to 50,000, and still more preferably 1,000 to 30, 000, particularly preferably 3,000 to 30,000, particularly preferably 5,000 to 30,000.
• the degree of dispersion [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (C) is preferably 1 to 6, more preferably 1 to 5, and further preferably 1 to 4.
• the acid value (in terms of solid content) of the resin (C) is preferably 10 to 500 mg-KOH / g, more preferably 20 to 450 mg-KOH / g, still more preferably 20 to 400 mg-KOH / g, and still more preferably Is 20 to 370 mg-KOH / g, more preferably 30 to 370 mg-KOH / g, still more preferably 30 to 350 mg-KOH / g, particularly preferably 30 to 340 mg-KOH / g, most preferably 30-335 mg-KOH / g.
• the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (C), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
• the content of the resin (C) is based on the total amount of solids.
• they are 1 mass% or more and 99 mass% or less, More preferably, it is 1 mass% or more and 95 mass% or less, More preferably, it is 3 mass% or more and 80 mass% or less, Especially preferably, it is 3 mass% or more and 60 mass% or less.
• the polymerizable compound (D) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (E), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.
• Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone. And the above-mentioned monomer (a), monomer (b) and monomer (c).
• Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol diester.
• Examples include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.
• the polymerizable compound (D) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
• examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( (Meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) ) Iso
• the weight average molecular weight of the polymerizable compound (D) is Preferably they are 50 or more and 4000 or less, More preferably, they are 50 or more and 3500 or less, More preferably, they are 50 or more and 3000 or less, Especially preferably, they are 150 or more and 2900 or less, Especially preferably, they are 250 or more and 1500 or less.
• the content of the polymerizable compound (D) is based on the total amount of solids in the colored curable resin composition. Preferably they are 1 mass% or more and 99 mass% or less, More preferably, it is 1 mass% or more and 95 mass% or less, More preferably, it is 3 mass% or more and 80 mass% or less, Especially preferably, it is 3 mass% or more and 60 mass% or less.
• Polymerization initiator (E) is not particularly limited as long as it is a compound that generates an active radical, an acid or the like by the action of light or heat and can initiate polymerization, and a known polymerization initiator can be used.
• Examples of the polymerization initiator (E) include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acyl phosphine oxide compounds.
• O-acyloxime compounds examples include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl)- 3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1- [9-ethyl -6- (2-Methylbenzoyl) -9H-carbazol-3-yl] ethane-1- N, acetoxy-1- [9
• O-acyloxime compound commercially available products such as Irgacure OXE01, OXE02 (above, manufactured by BASF Corporation) and N-1919 (produced by ADEKA Corporation) may be used.
• O-acyloxime compounds N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- At least one selected from the group consisting of 1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyl Oxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.
• alkylphenone compounds examples include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1- And 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one.
• Commercial products such as Irgacure 369, 907, 379 (above, manufactured by BASF Corporation) may be used as the alkylphenone compound.
• alkylphenone compound examples include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, Mention may also be made of 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, ⁇ , ⁇ -diethoxyacetophenone and benzyldimethyl ketal.
• biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 2,2′-bis (2,3-dichlorophenyl) -4.
• triazine compounds examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl)- 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-
• acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
• Commercial products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) may be used.
• the polymerization initiator (E) includes benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with a polymerization initiation assistant (E1) (particularly
• the polymerization initiator (E) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds, more preferably A polymerization initiator containing an O-acyloxime compound.
• the content of the polymerization initiator (E) is preferably 0.01% by mass or more and 40% by mass or less, more preferably 0.1% with respect to the total amount of the resin (C) and the polymerizable compound (D).
• the mass is 30% by mass or more.
• the colored curable resin composition of the present invention may contain a polymerization initiation assistant (E1).
• the polymerization initiation assistant (E1) is a compound or a sensitizer used for accelerating the polymerization of the polymerizable compound initiated by the polymerization initiator (E).
• the polymerization initiation assistant (E1) is included, it is usually used in combination with the polymerization initiator (E).
• Examples of the polymerization initiation assistant (E1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
• amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 4,4′-bis ( Ethylmethylamino) benzophenone, and the like, among which 4,4′-bis (diethylamino) benzophenone is preferred.
• Commercial products such as EAB-F (Hodogaya Chemical Co., Ltd.) may be used.
• alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy.
• Anthracene, 2-ethyl-9,10-dibutoxyanthracene and the like can be mentioned.
• thioxanthone compound examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.
• Carboxylic acid compounds include phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.
• the content is preferably 0.00001% by mass to 40% by mass with respect to the total amount of the resin (C) and the polymerizable compound (D). More preferably, it is 0.0001 mass% or more and 30 mass% or less.
• the colored curable resin composition can contain a solvent (F).
• a solvent (F) is not specifically limited, The solvent normally used in the said field
• Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate And methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and ⁇ -butyrolactone.
• Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, die Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, include phenetol and methyl anisole and the like.
• ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl acetate Le acetate, propylene glycol monopropyl ether
• Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone Etc.
• alcohol solvents examples include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
• aromatic hydrocarbon solvents examples include benzene, toluene, xylene and mesitylene.
• amide solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.
• These solvents may be used in combination of two or more.
• organic solvents having a boiling point of 120 ° C. or more and 180 ° C. or less at 1 atm are preferable from the viewpoints of coating properties and drying properties.
• the solvent preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2 -Pentanone and N, N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone Etc.
• the content of the solvent (F) is based on the total amount of the colored curable resin composition.
• it is 99.99 mass% or less, More preferably, it is 1 mass% or more and 99 mass% or less, More preferably, it is 10 mass% or more and 99 mass% or less, Especially preferably, it is 20 mass% or more and 99 mass% or less, More preferably, it is 30 mass% or more and 99 mass% or less, Especially preferably, it is 40 mass% or more and 99 mass% or less.
• Leveling agent (G) The colored curable resin composition of the present invention may further contain a leveling agent (G).
• a leveling agent examples include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
• silicone surfactants include surfactants having a siloxane bond in the molecule.
• Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name, manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (made by Momentive Performance Materials Japan GK) .
• fluorosurfactant examples include surfactants having a fluorocarbon chain in the molecule.
• Florard registered trademark
• FC430 FC431
• MegaFac registered trademark
• F142D F171, F172, F173, F177, F183, F183, F554, R30
• RS-718-K manufactured by DIC Corporation
• EFTOP registered trademark
• EF301 EF301
• EF303 EF351
• EF352 manufactured by Mitsubishi Materials Electronic Chemicals
• Surflon registered trademark
• SC101 SC105
• SC105 Asahi Glass Co., Ltd.
• E5844 Daikin Fine Chemical Laboratory Co., Ltd.
• silicone surfactant having a fluorine atom examples include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule.
• Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like can be given.
• the leveling agent (G) When the leveling agent (G) is contained, the content is based on the total amount of the colored curable resin composition, Usually 0.0001 mass% or more and 5 mass% or less, Preferably it is 0.0001 mass% or more and 3 mass% or less, More preferably, it is 0.001 mass% or more and 2 mass% or less, More preferably, it is 0.001 mass% or more and 1 mass% or less.
• the content of the leveling agent (G) is within the above range, the flatness of the color filter can be improved.
• the colored curable resin composition of the present invention may further contain an antioxidant (H).
• an antioxidant H
• antioxidants may be used alone or in combination of two or more.
• the antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, and the like can be used.
• phenolic antioxidant examples include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], manufactured by BASF Corporation), Irga Knox 1076 (Irganox 1076: Octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF Corporation), Irganox 1330 (Irganox 1330: 3, 3 ′, 3 ′′ 5,5 ′, 5 ′′ -hexa-tert-butyl-a, a ′, a ′′-(mesitylene-2,4,6-triyl) tri-p-cresol, manufactured by BASF Corporation), Iruga Knox 3114 (Irganox 3114: 1,3,5-Tris (3,5 Di-tert-butyl-4-hydroxybenzyl) -1,3,5-triflu
• Sumilizer BHT Sumilizer BHT, manufactured by Sumitomo Chemical Co., Ltd.
• Sumilizer GA-80 Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd.
• Sumizer GS Sumizer GS, manufactured by Sumitomo Chemical Co., Ltd.
• Cyanox 1790 Cyanox 1790, manufactured by Cytec Co., Ltd.
• Vitamin E manufactured by Eisai Co., Ltd.
• Examples of phosphorus antioxidants include Irgafos 168 (Irgafos 168: Tris (2,4-di-tert-butylphenyl) phosphite, manufactured by BASF Corporation), Irgafos 12 (Irgafos 12: Tris [2- [ [2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphin-6-yl] oxy] ethyl] amine (manufactured by BASF Corporation), Irgaphos 38 (Irgafos 38: bis (2,4-bis (1,1-dimethylethyl) -6-methylphenyl) ethyl ester phosphorous acid, manufactured by BASF Corp.), Adeka Stub 329K (manufactured by ADEKA Corp.), Adeka Stub PEP36 (manufactured by ADEKA Corporation), ADK ST
• sulfur-based antioxidants examples include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and ⁇ -alkyl mercaptopropionic acids of polyols such as tetrakis [methylene (3-dodecylthio) propionate] methane. An ester compound etc. are mentioned.
• the colored curable resin composition of the present invention is known in the art as necessary, such as fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, and the like.
• An additive may be included.
• the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycid.
• aliphatic carboxylic acid metal salt (A) -containing liquid containing an aliphatic carboxylic acid metal salt (A) and a solvent (F) was prepared in advance. Thereafter, a colored curable resin composition may be prepared using the aliphatic carboxylic acid metal salt (A) -containing liquid.
• the aliphatic carboxylic acid metal salt (A) is not dissolved in the solvent (F)
• the aliphatic carboxylic acid metal salt (A) -containing liquid is obtained by dispersing the aliphatic carboxylic acid metal salt (A) in the solvent (F). It may be prepared by mixing.
• the aliphatic carboxylic acid metal salt (A) -containing liquid may contain a part or all of the solvent (F) contained in the colored curable resin composition.
• the solid content in the aliphatic carboxylic acid metal salt (A) -containing liquid is based on the total amount of the aliphatic carboxylic acid metal salt (A) -containing liquid.
• they are 0.01 mass% or more and 99.99 mass% or less, More preferably, it is 0.1 mass% or more and 90 mass% or less, More preferably, it is 0.1 mass% or more and 50 mass% or less, Especially preferably, it is 0.2 mass% or more and 50 mass% or less, More preferably, it is 0.5 mass% or more and 30 mass% or less.
• the content of the aliphatic carboxylic acid metal salt (A) in the aliphatic carboxylic acid metal salt (A) -containing liquid is the total amount of solids in the aliphatic carboxylic acid metal salt (A) -containing liquid, 100% by mass or less, Preferably they are 0.1 mass% or more and 100 mass% or less, More preferably, it is 1 mass% or more and 90 mass% or less, More preferably, it is 3 mass% or more and 80 mass% or less, Especially preferably, it is 5 mass% or more and 70 mass% or less, More preferably, it is 10 mass% or more and 70 mass% or less.
• Aliphatic carboxylic acid metal salt (A) if necessary, rosin treatment, surface treatment using aliphatic carboxylic acid metal salt (A) derivative into which acidic group or basic group is introduced, polymer compound, etc.
• the particle size of the aliphatic carboxylic acid metal salt (A) is preferably substantially uniform.
• the aliphatic carboxylic acid metal salt (A) is uniformly dispersed in the aliphatic carboxylic acid metal salt (A) -containing liquid by carrying out a dispersion treatment by containing a dispersant. It can be in a distributed state.
• a plurality of types of aliphatic carboxylic acid metal salts (A) may each be subjected to dispersion treatment alone, or a plurality of types may be mixed and dispersed.
• dispersant examples include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specific examples include polyester-based, polyamine-based, and acrylic surfactants. These dispersants may be used alone or in combination of two or more.
• KP Japanese Patent Application Laidiol
• Floren manufactured by Kyoeisha Chemical Co., Ltd.
• Solsperse registered trademark
• Geneca Corporation EFKA (registered trademark) (Manufactured by BASF Corp.)
• Azisper registered trademark
• DISPERBYK registered trademark
• BYK Chemie Corp. BYK (registered trademark) (manufactured by BYK Chemie Corp.)
• BYK registered trademark
• the amount of the dispersant (solid content) used is 100 parts by mass of the aliphatic carboxylic acid metal salt (A).
• 0.01 parts by mass or more and 10000 parts by mass or less Preferably they are 0.01 mass part or more and 5000 mass parts or less, More preferably, it is 0.01 to 1000 parts by mass, More preferably, it is 0.1 to 500 parts by mass, Particularly preferably, it is 0.1 parts by mass or more and 300 parts by mass or less, More preferably, it is 1 to 300 parts by mass, Particularly preferably, it is 5 parts by mass or more and 260 parts by mass or less.
• the amount of the dispersant used is within the above range, a more uniformly dispersed aliphatic carboxylic acid metal salt (A) -containing liquid tends to be obtained.
• the aliphatic carboxylic acid metal salt (A) -containing liquid After preparing the aliphatic carboxylic acid metal salt (A) -containing liquid containing the aliphatic carboxylic acid metal salt (A) and the solvent (F) in advance, the aliphatic carboxylic acid metal salt (A) -containing liquid is used.
• the aliphatic carboxylic acid metal salt (A) -containing liquid is a part or all of the resin (C) contained in the colored curable resin composition, preferably one. May be included in advance. By including the resin (C) in advance, the dispersion stability of the aliphatic carboxylic acid metal salt (A) -containing liquid can be further improved.
• the content of the resin (C) is 100 parts by mass of the aliphatic carboxylic acid metal salt (A).
• 0.01 parts by mass or more and 10000 parts by mass or less Preferably they are 0.01 mass part or more and 5000 mass parts or less, More preferably, it is 0.01 to 1000 parts by mass, More preferably, it is 0.1 to 500 parts by mass, Especially preferably, it is 0.1 to 300 parts by mass.
• the colored curable resin composition of the present invention contains a solvent (F)
• a colorant-containing liquid containing a colorant and a solvent (F) is prepared in advance, and then the colorant-containing liquid is used for color curable.
• a resin composition may be prepared.
• the colorant-containing liquid can be prepared by dispersing and mixing the colorant in the solvent (F).
• the colorant-containing liquid may contain a part or all of the solvent (F) contained in the colored curable resin composition.
• the solid content in the colorant-containing liquid is based on the total amount of the colorant-containing liquid.
• they are 0.01 mass% or more and 99.99 mass% or less, More preferably, it is 0.1 mass% or more and 99.9 mass% or less, More preferably, it is 0.1 mass% or more and 99 mass% or less, Particularly preferably, it is 1 to 90% by mass, More preferably, it is 1 mass% or more and 70 mass% or less, More preferably, it is 3 mass% or more and 60 mass% or less, Particularly preferably, it is 3% by mass or more and 50% by mass or less, Most preferably, it is 5 mass% or more and 40 mass% or less.
• the content of the colorant in the colorant-containing liquid is the total amount of solids in the colorant-containing liquid, 100% by mass or less, Preferably it is 0.0001 mass% or more and 99.9999 mass% or less, More preferably, it is 0.0001 mass% or more and 99 mass% or less, More preferably, it is 1 mass% or more and 99 mass% or less, Especially preferably, it is 10 mass% or more and 99 mass% or less, More preferably, it is 20 mass% or more and 99 mass% or less.
• the colorant may be rosin treatment, surface treatment using a colorant derivative having an acidic group or basic group introduced, grafting to the surface of the colorant with a polymer compound, sulfuric acid atomization method, etc. May be subjected to atomization treatment, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, and the like.
• the particle size of the colorant is preferably substantially uniform.
• the colorant can be in a state where the colorant is uniformly dispersed in the colorant-containing liquid by carrying out a dispersion treatment by adding a dispersant.
• Each of the colorants may be dispersed alone, or a plurality of colorants may be mixed and dispersed.
• dispersant examples include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specific examples include polyester-based, polyamine-based, and acrylic surfactants. These dispersants may be used alone or in combination of two or more.
• KP Japanese Patent Application Laidiol
• Floren manufactured by Kyoeisha Chemical Co., Ltd.
• Solsperse registered trademark
• Geneca Corporation EFKA (registered trademark) (Manufactured by BASF Corp.)
• Azisper registered trademark
• DISPERBYK registered trademark
• BYK Chemie Corp. BYK (registered trademark) (manufactured by BYK Chemie Corp.)
• BYK registered trademark
• the amount of the dispersant (solid content) used is 100 parts by weight of the colorant.
• 0.01 parts by mass or more and 10000 parts by mass or less Preferably they are 0.01 mass part or more and 5000 mass parts or less, More preferably, it is 0.01 to 1000 parts by mass, More preferably, it is 0.1 to 500 parts by mass, Particularly preferably, it is 0.1 parts by mass or more and 300 parts by mass or less, More preferably, it is 0.1 to 200 parts by mass, Particularly preferably, it is 5 parts by mass or more and 150 parts by mass or less.
• the colorant-containing liquid is: Part or all, preferably part of the resin (C) contained in the colored curable resin composition may be included in advance.
• resin (C) in advance, the dispersion stability of the colorant-containing liquid can be further improved.
• the content of the resin (C) is 100 parts by weight of the colorant.
• 0.01 parts by mass or more and 10000 parts by mass or less Preferably they are 0.01 mass part or more and 5000 mass parts or less, More preferably, it is 0.01 to 1000 parts by mass, More preferably, it is 1 to 500 parts by mass, Particularly preferably, it is 5 parts by mass or more and 200 parts by mass or less, More preferably, they are 5 to 150 mass parts.
• a color filter can be formed from the colored curable resin composition of the present invention.
• the method for forming the colored pattern include a photolithographic method, an ink jet method, and a printing method. Of these, the photolithographic method is preferable.
• the photolithographic method the colored curable resin composition is applied to a substrate and dried to form a colored curable resin composition layer, and the colored curable resin composition layer is exposed through a photomask, This is a developing method.
• a colored coating film that is a cured product of the colored composition layer can be formed by not using a photomask and / or not developing during exposure. The colored pattern and the colored coating film thus formed are the color filter of the present invention.
• the film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose and application.
• it is 0.1 to 30 ⁇ m, preferably 0.1 to 20 ⁇ m, and more preferably. Is 0.5 to 6 ⁇ m.
• a glass plate, a resin plate, silicon, or an aluminum, silver, silver / copper / palladium alloy thin film formed on the substrate is used.
• another color filter layer, a resin layer, a transistor, a circuit, or the like may be formed.
• Formation of each color pixel by the photolithographic method can be performed by a known or commonly used apparatus and conditions. For example, it can be produced as follows. First, a colored curable resin composition is applied onto a substrate, dried by heating (prebaking) and / or drying under reduced pressure to remove volatile components such as a solvent, and a smooth colored curable resin composition layer is formed. obtain. Examples of the coating method include spin coating, slit coating, and slit and spin coating.
• Exposure apparatus such as a mask aligner and a stepper can irradiate a parallel light beam uniformly on the entire exposure surface and can perform accurate alignment between a photomask and a substrate on which a colored curable resin composition layer is formed. Is preferably used.
• a colored pattern is formed on the substrate.
• the unexposed portion of the colored curable resin composition layer is dissolved and removed in the developer.
• an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide is preferable.
• the developing method may be any of paddle method, dipping method, spray method and the like.
• the substrate may be tilted at an arbitrary angle during development.
• the substrate after development is preferably washed with water. Furthermore, it is preferable to post-bake the obtained colored pattern.
• the color filter is useful as a color filter used for a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor, and particularly as a color filter used for a liquid crystal display device.
• the polystyrene-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
• Detector RI
• Calibration standard materials TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
• the ratio (Mw / Mn) of the weight average molecular weight (Mw) and number average molecular weight (Mn) in terms of polystyrene obtained above was defined as the dispersity.
• ⁇ Synthesis Example 1 Synthesis of Aliphatic Carboxylic Acid Metal Salt (A1)> 108 parts of 12-hydroxystearic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 2040 parts of water were mixed. To this mixture, 1320 parts of a 1% aqueous sodium hydroxide solution was added at 70 ° C. The mixture was stirred at 70 ° C. for about 1 hour 30 minutes. To this mixture, a mixture of 44.4 parts of iron (III) nitrate nonahydrate (manufactured by Wako Pure Chemical Industries, Ltd.) and 825 parts of water was maintained for about 2 hours and 30 minutes while maintaining 70 to 75 ° C. It was dripped over.
• A1 Aliphatic Carboxylic Acid Metal Salt
• the mixture was stirred for about 1 hour while maintaining at 70 ° C. to 75 ° C.
• the mixture was cooled to 35 ° C. and filtered.
• the obtained residue was washed 3 times with 5000 parts of water.
• the obtained residue was dried at 60 ° C. under reduced pressure to obtain 112 parts of an aliphatic carboxylic acid metal salt (A1).
• Dispersion (A1) 250 parts of an aliphatic carboxylic acid metal salt (A1); 421 parts of a dispersant (DISPERBYK-111; manufactured by Big Chemie Japan Co., Ltd.); Solvent (F): 8330 parts propylene glycol monomethyl ether acetate; and Solvent (F): 1000 parts 4-hydroxy-4-methyl-2-pentanone; Were mixed to disperse the aliphatic carboxylic acid metal salt (A1) to obtain a dispersion (A1).
• Pigment Green 58 Dispersion (B2) Preparation of Pigment Green 58 Dispersion (Pigment Dispersion (B2)> Pigment: C.I. I. Pigment green 58 14.0 parts; Pigment dispersant 2.80 parts; Resin (C): Resin (C1) 2.90 parts; and Solvent (F): Propylene glycol monomethyl ether acetate 80.3 parts; And the pigment was dispersed using a bead mill to obtain a pigment dispersion (B2).
• Pigment Yellow 185 Dispersion (B4) Preparation of Pigment Yellow 185 Dispersion (Pigment Dispersion (B4)> Pigment: C.I. I. Pigment yellow 185 7.96 parts; Pigment dispersant 5.17 parts; Resin (C): Resin (C1) 2.79 parts; and Solvent (F): Propylene glycol monomethyl ether acetate 84.08 parts; Were mixed and the pigment was dispersed using a bead mill to obtain a pigment dispersion (B4).
• copolymer solution (resin (C1) solution) having a solid content of 25.6%.
• the acid value (in terms of solid content) of the resin (C1) solution was 109 mg-KOH / g.
• the resulting copolymer had a weight average molecular weight Mw of 8000 and a dispersity of 2.1.
• Examples 1 and 2 and Comparative Examples 1 and 2 (1) Preparation of colored curable resin composition
• the components described in Table 1 were mixed in the blending amounts shown in Table 1 to obtain a colored curable resin composition.
• the unit of the amount of each component in Table 1 is “part by mass”.
• the colored curable resin composition layer after light irradiation is immersed and developed at 24 ° C. for 60 seconds in an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide, washed with water, Was used and post-baked at 230 ° C. for 20 minutes to obtain a colored pattern. It was 2.4 micrometers when the film thickness of the obtained colored pattern was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.).
• the colored curable resin composition of the present invention it is possible to provide a color filter having a small degree of lightness reduction even if it contains a metal compound, and a display device including the color filter.

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• 2019
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