WO2021044860A1 - Composition colorante pour matrice noire, et filtre couleur - Google Patents

Composition colorante pour matrice noire, et filtre couleur Download PDF

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Publication number
WO2021044860A1
WO2021044860A1 PCT/JP2020/031448 JP2020031448W WO2021044860A1 WO 2021044860 A1 WO2021044860 A1 WO 2021044860A1 JP 2020031448 W JP2020031448 W JP 2020031448W WO 2021044860 A1 WO2021044860 A1 WO 2021044860A1
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WIPO (PCT)
Prior art keywords
group
coloring composition
black matrix
mass
dispersant
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PCT/JP2020/031448
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English (en)
Japanese (ja)
Inventor
達彦 清水
井上　智晶
康人 辻
智宏 鍋田
Original Assignee
大塚化学株式会社
サカタインクス株式会社
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Publication date
Application filed by 大塚化学株式会社, サカタインクス株式会社 filed Critical 大塚化学株式会社
Priority to CN202080042212.XA priority Critical patent/CN113939768A/zh
Priority to KR1020217040298A priority patent/KR20220060502A/ko
Publication of WO2021044860A1 publication Critical patent/WO2021044860A1/fr

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    • 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
    • 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
    • C08K5/13—Phenols; Phenolates
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—Photochromic 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
    • 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
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133512—Light shielding layers, e.g. black matrix
    • 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
    • G03F7/09—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 coloring composition for a black matrix.
  • a color filter used in an image display device such as a liquid crystal display is a boundary between color pixels that transmit light of the three primary colors of red (R), green (G), and blue (B) formed on a transparent substrate and each color pixel. It consists of a black matrix that is formed in black and does not substantially transmit visible light as black.
  • a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for orienting the liquid crystal in a certain direction is formed on the transparent electrode.
  • an alignment film for orienting the liquid crystal in a certain direction is formed on the transparent electrode.
  • a coloring composition in which a pigment, a dispersant, a binder resin and a dispersion medium (solvent) are mixed is used.
  • the colored composition is first applied to a transparent substrate, and a coating film made of the colored composition is formed on the transparent substrate.
  • the binder resin is cured by irradiating radiation (hereinafter referred to as "exposure") through a photomask having a desired pattern shape.
  • the unexposed portion is removed by development to form a colored layer having a desired pattern shape.
  • the colored layer is subjected to a treatment such as heating as necessary.
  • a color filter can be manufactured by forming a black pattern (hereinafter referred to as "black matrix”) and color pixels of red (R), green (G), and blue (B).
  • the black matrix is formed in a grid pattern or a band shape, is a thin film and details, and is required to have sharp edges and high linearity.
  • a coloring composition using carbon black as a light-shielding material has been used for forming a black matrix.
  • carbon black is dispersed in the coloring composition, there is a problem that reaggregation is likely to occur as the surface area of carbon black increases, and the dispersion stability is lowered.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a coloring composition for a black matrix, which has high dispersion performance of a coloring material and a small amount of formaldehyde generated over time.
  • the coloring composition for a black matrix of the present invention which has been able to solve the above problems, contains a coloring material, a dispersant, a dispersion medium and a phosphite ester, and the phosphite ester is represented by the general formula (5). It is characterized by being a represented compound.
  • R 51 represents an alkyl group having 1 to 20 carbon atoms.
  • R 52 and R 53 each independently represent a hydrocarbon group.
  • R 52 and R 53 may be coupled to each other to form a cyclic structure.
  • the compound represented by the general formula (5) may be bonded at R 52 or R 53 to form a dimer or a trimer.
  • a coloring composition for a black matrix which has high dispersion performance of a coloring material and a small amount of formaldehyde generated over time.
  • (meth) acrylic refers to "at least one of acrylic and methacrylic”.
  • (Meta) acrylate refers to "at least one of acrylate and methacrylate”.
  • the coloring composition for a black matrix of the present invention (hereinafter, may be simply referred to as “coloring composition”) contains a coloring material, a dispersant, a dispersion medium and a phosphite ester, and the phosphite ester is , It is a compound represented by the general formula (5).
  • the coloring composition for black matrix does not substantially transmit visible light.
  • the optical density (OD value) of the black resist pattern formed from the coloring composition is preferably 0.5 or more, more preferably 1.0 or more, still more preferably 1.5 or more.
  • the coloring composition was applied onto a glass substrate with a spin coater so as to have a film thickness of 1 ⁇ m, and a black resist pattern was formed only on the solid portion.
  • a Macbeth densitometer TD- Measured using 931, manufactured by Macbeth.
  • the coloring material a known coloring material can be used without particular limitation as long as the coloring composition can have a black or pseudo-black hue.
  • the "pseudo-blackened hue” is ideally black, but any hue that is acceptable as a black matrix used in the color filter of the liquid crystal display element may be used.
  • the black matrix basically needs to be achromatic so as not to add extra color. Further, when light leaks from the black matrix, the contrast of the image is lowered. Therefore, black is ideal as described above in that it absorbs all the light of each color. However, it does not have to be completely achromatic, as long as it is in the range of hues that do not add extra color to the image, and the hues that can absorb the light required to maintain contrast are pseudo-blackened. It is included in the hue range.
  • coloring material examples include black pigments, mixed color pigments, and mixtures thereof.
  • black pigment examples include carbon black, graphite, perylene pigment, lactam pigment, titanium black, metal oxides such as copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium and silver, and composite oxides. , Metal sulfide, metal sulfate, metal carbonate and the like. Among these, carbon black and titanium black are preferable from the viewpoint of shading rate and image characteristics. Examples of the carbon black include furnace black, channel black, acetylene black, thermal black, lamp black, and bone black. Further, as the carbon black, either neutral carbon black or acidic carbon black can be used, and these may be used in combination.
  • the hue of the black pigment is not limited to black, which is an achromatic color in terms of color theory, and may be purplish black, bluish black, or reddish black.
  • Examples of the mixed color pigment include those obtained by mixing two or more kinds of pigments other than the black pigment to make them pseudo-black.
  • As the color mixing pigment two or more kinds of organic pigments selected from the group consisting of blue organic pigments, purple organic pigments, yellow organic pigments, red organic pigments and orange organic pigments were mixed and pseudo-blackened. Things can be mentioned.
  • Examples of the blue organic pigment include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 22, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 64, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like. Be done.
  • Examples of purple organic pigments include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 30, 31, 32, 37, 39, 40, 42, 44, 47, 49, 50 and the like can be mentioned.
  • Examples of the yellow organic pigment include C.I.
  • red organic pigment examples include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 49: 2, 50: 1, 52: 1, 52: 2, 53, 53: 1, 53: 2, 53: 3, 57, 57: 1, 57: 2, 58: 4, 60, 63, 63: 1, 63: 2, 64, 64: 1, 68, 69, 81, 81: 1, 81: 2, 81: 3, 81: 4, 83, 88, 90: 1, 97, 101, 101: 1, 104, 108, 108: 1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 184, 185, 187, 188, 190
  • orange organic pigment examples include C.I. I. Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 51, 55, 59, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79 and the like can be mentioned.
  • a combination of a blue organic pigment and at least two or more kinds of organic pigments selected from purple, yellow, red, and orange organic pigments is preferable.
  • the coloring material may contain a dye derivative as a dispersion aid.
  • the dye derivative preferably contains a dye derivative having an acidic group.
  • This dye derivative has an acidic functional group introduced into the dye skeleton.
  • Specific examples of the pigment skeleton include an azo pigment skeleton, a phthalocyanine pigment skeleton, an anthraquinone pigment skeleton, a triazine pigment skeleton, an aclysin pigment skeleton, and a perylene pigment skeleton.
  • As the acidic group introduced into the dye skeleton a carboxy group, a phosphoric acid group and a sulfonic acid group are preferable. A sulfonic acid group is preferable for convenience of synthesis and strength of acidity.
  • the acidic group may be directly bonded to the dye skeleton, or may be bonded to the dye skeleton via a hydrocarbon group such as an alkyl group or an aryl group; an ester, an ether, a sulfonamide, or a urethane bond.
  • the total content of the coloring material in the coloring composition is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, and 80% by mass, based on the total solid content of the coloring composition.
  • the following is preferable, more preferably 70% by mass or less, still more preferably 60% by mass or less.
  • the solid content is a component in the coloring composition other than the dispersion medium described later.
  • the coloring composition contains a dispersant.
  • the dispersant has a portion having a property of adsorbing to the coloring material and a moiety having an affinity with the dispersion medium.
  • the dispersant has a function of adsorbing on a coloring material and stabilizing dispersion in a dispersion medium.
  • the dispersant is not particularly limited, and may be appropriately selected depending on the type of the colorant and the dispersion medium.
  • the resin-type dispersant used in the coloring composition for a color filter can be used.
  • the resin type dispersant examples include the following. (1) From the group consisting of an amino group and / or an imino group of a polyamine compound (for example, polyalkyleneamine such as polyallylamine, polyvinylamine, polyethylene polyimine) and polyester, polyamide and polyesteramide having a free carboxy group. Reaction product with at least one selected. (2) A carbodiimide-based compound having at least one side chain selected from the group consisting of a polyester side chain, a polyether side chain, and a polyacrylic side chain and at least one basic nitrogen-containing group in the molecule. .. (3) A reaction product of an amino compound such as polyalkyleneimine or methyliminobispropylamine and a polyester having a free carboxy group.
  • a polyamine compound for example, polyalkyleneamine such as polyallylamine, polyvinylamine, polyethylene polyimine
  • polyester for example, polyalkyleneamine such as polyallylamine, polyvinylamine, polyethylene polyimine
  • polyester
  • Polyisocyanate compounds such as alcohols such as methoxypolyisocyanate glycol and polyesters having one hydroxyl group such as caprolactone polyester, compounds having 2 to 3 isocyanate group reactive functional groups, and isocyanate group reactive.
  • a reaction product obtained by reacting a compound having an isocyanate group with a compound having an amino group A reaction product obtained by reacting a polyepoxy compound with a linear polymer having a free carboxy group and an organic amine compound having one secondary amino group.
  • At least one kind, at least one kind of basic group-containing polymerizable monomer such as (meth) acrylamide, N-methylolamide, vinyl imidazole, vinylpyridine, a monomer having an amino group and a polycaprolactone skeleton, and a styrene, a styrene derivative, A copolymer with at least one of other polymerizable monomers.
  • (12) A compound obtained by carrying out a Michael addition reaction of a polycarbonate compound with polyallylamine.
  • a carbodiimide-based compound having at least one polybutadiene chain and one basic nitrogen-containing group A carbodiimide-based compound having at least one side chain having an amide group and at least one basic nitrogen-containing group in the molecule.
  • a basic group-containing urethane-based resin-type dispersant a basic group-containing polyester-based resin-type dispersant, and a basic group-containing (meth) acrylic resin-type dispersant are more preferable, and an amino group-containing dispersant is preferable.
  • Urethane-based resin-type dispersants, amino group-containing polyester-based resin-type dispersants, and amino group-containing (meth) acrylic-based resin-type dispersants are more preferable.
  • a basic group-containing urethane resin type dispersant is preferable, and among these, a basic group (amino group) -containing urethane having at least one selected from the group consisting of a polyester chain, a polyether chain, and a polycarbonate chain.
  • a resin-based dispersant is preferable.
  • the resin type dispersant is preferably a resin (polymer) having a polar functional group. It is considered that the polar functional group has a function of adsorbing to the pigment and stabilizing the dispersion in the dispersion medium.
  • the polar functional group include a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium base, an imino group, an amide group, a nitrogen-containing heterocyclic group, a carboxy group, a phosphoric acid group and a sulfonic acid group. Can be mentioned.
  • polar functional group at least one selected from a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium base, an imino group, an amide group and a nitrogen-containing heterocyclic group is preferable.
  • the resin-type dispersant includes a polymer having an amine value and no acid value (a polymer having an amine value of more than 0 mgKOH / g and an acid value of 0 mgKOH / g), and a polymer having an acid value and having an amine value.
  • Non-polymer polymer with acid value over 0 mgKOH / g and amine value over 0 mgKOH / g
  • polymer with amine value and acid value polymer with amine value and acid value over 0 mgKOH / g
  • acid value and there are polymers that do not have an amine value (polymers with an amine value and acid value of 0 mgKOH / g).
  • the resin type dispersant a polymer having an amine value (a polymer having an amine value of more than 0 mgKOH / g) is preferable.
  • the amine value of the resin-type dispersant is preferably 10 mgKOH / g or more and 200 mgKOH / g or less.
  • the resin type dispersant preferably has an acid value of less than 20 mgKOH / g.
  • the content of the dispersant in the coloring composition is preferably 1 part by mass or more, more preferably 2 parts by mass or more, still more preferably 5 parts by mass or more, and particularly preferably 10 parts by mass or more with respect to 100 parts by mass of the coloring material. It is preferably 200 parts by mass or less, more preferably 100 parts by mass or less, and further preferably 50 parts by mass or less.
  • the coloring composition contains a dispersion medium.
  • the dispersion medium is appropriately selected as long as it disperses or dissolves other components (solids) constituting the coloring composition, does not react with these components, and has appropriate volatility.
  • a conventionally known organic solvent can be used, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol mono-n-butyl ether, propylene glycol monomethyl ether.
  • Glycolalkyl Ether acetates such as ethylene glycol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate; Alkyl acetates such as cyclohexanol acetate; Amyl ether, propyl ether, diethyl ether , Dipropyl ether, diisopropyl ether, butyl ether, diamyl ether, ethyl isobutyl ether, dihexyl ether and other ethers; acetone, methyl ethyl ketone, 2-heptanone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone.
  • Alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, and bicyclohexyl; aromatic hydrocarbons such as benzene, toluene, xylene, and cumene; amylformate, ethylformate, ethyl acetate , Butyl acetate, propyl acetate, amyl acetate, methyl isobutyrate, ethylene glycol acetate, ethyl propionate, propyl propionate, butyl butyrate, isobutyl butyrate, methyl isobutyrate, ethyl caprilate, butyl stearate, ethyl benzoate, Methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionat
  • the organic solvent contains diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene from the viewpoints of dispersibility of the coloring material and the like, solubility of the dispersant, and coatability of the coloring composition.
  • Glycol monoethyl ether acetate, cyclohexanone, 2-heptanone, amylformate, ethyl 2-hydroxypropionate, butyl 3-methyl-3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate and the like are preferable. ..
  • the dispersion medium contained in the coloring composition may be only one type or may be a plurality of types.
  • the content of the dispersion medium in the coloring composition is not particularly limited and can be adjusted as appropriate.
  • the content of the dispersion medium in the coloring composition is usually 99% by mass or less.
  • the content of the dispersion medium in the coloring composition is preferably 50% by mass or more in consideration of the viscosity suitable for coating the coloring composition.
  • the coloring composition of the present invention contains a phosphite ester represented by the general formula (5). By containing the phosphite ester, formaldehyde generated from the compounding agent in the coloring composition can be reduced.
  • R 51 represents an alkyl group having 1 to 20 carbon atoms.
  • R 52 and R 53 each independently represent a hydrocarbon group.
  • R 52 and R 53 may be coupled to each other to form a cyclic structure.
  • the compound represented by the general formula (5) may be bonded at R 52 or R 53 to form a dimer or a trimer.
  • R 51 represents an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a hexyl group, an isohexyl group, a heptyl group, an isoheptyl group and an octyl group.
  • Examples of the hydrocarbon group represented by R 52 or R 53 include an alkyl group which may have a substituent and an aromatic group which may have a substituent.
  • the total number of carbon atoms of the alkyl group which may have the substituent is preferably 1 to 20, more preferably 1 to 15.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a hexyl group, an isohexyl group, a heptyl group, an isoheptyl group, an octyl group and an isooctyl group.
  • aromatic group examples include a phenyl group, a toluyl group, a xylyl group, a cumenyl group, a mesityl group, a benzyl group, a phenethyl group, a styryl group, a cinnamyl group, a benzhydryl group, a trityl group, an ethylphenyl group, a propylphenyl group and a butylphenyl group.
  • Examples thereof include a group, a pentylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, a decylphenyl group, an undecylphenyl group and a dodecylphenyl group.
  • R 52 and R 53 may be coupled to each other to form a cyclic structure. Examples of the ring formed by connecting R 52 and R 53 to each other include the following partial structures. Further, the compound represented by the general formula (5) may be bonded by R 52 or R 53 to form a dimer or a trimer.
  • the phosphite ester represented by the general formula (5) includes a phosphite ester represented by the general formula (5-1) and / or a phosphite ester represented by the general formula (5-2). Is preferable.
  • R 51 represents an alkyl group having 1 to 20 carbon atoms. A plurality of R 51s may be the same or different from each other. ]
  • R 51 represents an alkyl group having 1 to 20 carbon atoms. A plurality of R 51s may be the same or different from each other. ]
  • Examples of the phosphite ester represented by the general formula (5) include triethyl phosphite, tripropyl phosphite, triisopropyl phosphite, tributyl phosphite, trypentyl phosphite, trihexyl phosphite, and sub-phosphate.
  • Trialkyl phosphites such as trioctyl phosphate, triisooctyl phosphite, trinonyl phosphite, tridecyl phosphite, triisodecyl phosphite; octyldiphenyl phosphite, decyldiphenyl phosphite, diphenyl phosphite Alkyl phosphite esters such as isodecyl, tridecyldiphenyl phosphite, hexadecyldiphenyl phosphate; 3,9-bis (octadecyloxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro [5,5] Undecane, 3,9-bis (isodecyloxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro [5,5] Di
  • the phosphite ester represented by the general formula (5) contained in the coloring composition may be of only one type or of a plurality of types.
  • the content of the phosphite ester represented by the general formula (5) in the coloring composition is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, based on 100 parts by mass of the dispersant. It is more preferably 1 part by mass or more, particularly preferably 5 parts by mass or more, preferably 100 parts by mass or less, more preferably 80 parts by mass or less, still more preferably 60 parts by mass or less, and particularly preferably 25 parts by mass or less. Is.
  • the phosphite ester may be added to the coloring material and / or the dispersant before mixing the coloring material and the dispersant, or the coloring material and the dispersant are mixed. It may be added at the time, or it may be added to this mixture after mixing the colorant and the dispersant.
  • the coloring composition of the present invention can contain a known phenolic antioxidant.
  • a phenolic antioxidant By containing a phenolic antioxidant, the amount of formaldehyde in the coloring composition can be further reduced. The reason why the amount of formaldehyde can be reduced is considered to be that the oxidative deterioration of the phosphite ester can be suppressed.
  • the dispersion stability of the coloring material can be improved even when the coloring composition contains a large amount of binder resin. In particular, when the binder resin content in the total solid content of the coloring composition is 30% by mass or more, the effect of improving the dispersion stability becomes remarkable.
  • a phenolic antioxidant is an antioxidant having a compound having at least one hydroxy group on at least one benzene ring. Specifically, when the hydroxy group on the benzene ring is the 1-position, at least one of the 2-position, 4-position and 6-position, or at least one of the 3-position, 4-position and 6-position has a radical. Substituents that can eliminate the molecule of, for example, bulky substituents (eg, substituents in which the carbon atom bonded to the benzene ring is a quaternary carbon atom (specific example, t-butyl group, adamantyl group, etc.)) An antioxidant having a chemical structure having a
  • phenolic antioxidant a compound represented by the general formula (6) is preferable.
  • R 61 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 62 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 63 represents a group in which any one or more carbon atoms of the hydrocarbon group having 2 to 20 carbon atoms is substituted with an ester group or an ether group, or a hydrocarbon group having 1 to 20 carbon atoms.
  • n represents a number from 1 to 6.
  • the carbon atom bonded to the benzene ring of R 61 is a primary to tertiary carbon atom.
  • R 61 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a hexyl group, an isohexyl group, a heptyl group, an isoheptyl group and an octyl group.
  • Groups, isooctyl groups and the like can be mentioned.
  • a hydrogen atom, a methyl group, and an ethyl group are preferable, a hydrogen atom and a methyl group are more preferable, and a hydrogen atom is further preferable, because the synergistic effect of the antioxidant performance is large.
  • the carbon atom bonded to the benzene ring does not become a quaternary carbon atom, and for example, a group such as a tert-butyl group is not suitable for R 61 .
  • R 62 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group and a tert-butyl group, and a methyl group is preferable.
  • R 63 represents a group in which any one or more carbon atoms of the hydrocarbon group having 2 to 20 carbon atoms is substituted with an ester group or an ether group, or a hydrocarbon group having 1 to 20 carbon atoms.
  • the hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a hexyl group, an isohexyl group, a heptyl group and an isoheptyl group.
  • Octyl group isooctyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, isoundecyl group, dodecyl group, isododecyl group, tridecyl group, isotridecyl group, tetradecyl group, isotetradecyl group, hexadecyl group, isohexadecyl Alkyl groups such as groups, octadecyl groups, isooctadecyl groups, eicosyl groups; vinyl groups, allyl groups, propenyl groups, isopropenyl groups, butenyl groups, isobutenyl groups, pentenyl groups, isopentenyl groups, hexenyl groups, heptenyl groups, octenyl groups.
  • an alkyl group is preferable, and an alkyl group having 1 to 10 carbon atoms is more preferable.
  • the above group is a group when the value of n in the general formula (6) is 1, and when the value of n is 2, it is a group obtained by removing one arbitrary hydrogen atom from the above group. If the value is 3, it becomes a group obtained by removing two arbitrary hydrogen atoms from the above group.
  • the value of n represents a number of 1 to 6, but the number of 1 to 4 is preferable, and the number of 2 or 3 is more preferable because the performance as an antioxidant is good and the raw material conditions are good.
  • R 63 may be a group in which one or more carbon atoms of any of the hydrocarbon groups having 2 to 20 carbon atoms are substituted with an ester group or an ether group.
  • the group may have only one of an ester group and an ether group, a group having both, or a group having a plurality of the groups.
  • R 63 is preferably a hydrocarbon group having 1 to 20 carbon atoms.
  • the compound of the general formula (6) include 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane and 4,4'-butylidenebis (6-tert-butyl).
  • -M-cresol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionic acid] [ethylene bis (oxyethylene)], bis [3- (3-tert-butyl-4) -Hydroxy-5-methylphenylpropionic acid] (2,4,8,10-tetraoxaspiro [5,5] undecane-3,9-diyl) bis (2,2-dimethyl-2,1-ethanediyl)) And so on.
  • the phenolic antioxidant contained in the coloring composition may be of only one type or of a plurality of types.
  • the content of the phenolic antioxidant is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, still more preferably 1 part by mass or more with respect to 100 parts by mass of the dispersant. It is preferably 25 parts by mass or less, more preferably 10 parts by mass or less, still more preferably 5 parts by mass or less, and particularly preferably 2 parts by mass or less.
  • the phenolic antioxidant may be added to the colorant and / or the dispersant before mixing the colorant and the dispersant, or the colorant and the dispersant may be mixed. It may be added at the time of preparation, or it may be added to this mixture after mixing the colorant and the dispersant.
  • the phenolic antioxidant is preferably added to the colorant and / or the dispersant before mixing the colorant and the dispersant.
  • the coloring composition of the present invention can contain a binder resin (however, the dispersant is excluded).
  • the binder resin include alkali-soluble resins and polymerizable compounds (polymerizable resins, monomers having one polymerizable unsaturated bond in the molecule, monomers having two or more polymerizable unsaturated bonds in the molecule, oligomers, etc.). , Thermosetting resin, thermoplastic resin and the like. These can be used alone or in combination of two or more. Among these, alkali-soluble resins and / or polymerizable compounds are preferable.
  • the binder resin is a compound different from the resin type dispersant.
  • the binder resin preferably has an amine value of 0 mgKOH / g.
  • the content of the binder resin in the coloring composition is the total amount of the binder resins used, and is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 5% by mass, based on the total solid content of the coloring composition. As described above, it is preferably 70% by mass or less, more preferably 60% by mass or less, and further preferably 50% by mass or less.
  • the alkali-soluble resin may be one that acts as a binder for the coloring material and is soluble in a developing solution, preferably an alkali developing solution, that is used in the developing process when producing a color filter.
  • a developing solution preferably an alkali developing solution
  • the alkali-soluble resin is preferably a resin having an acidic group such as a carboxy group or a phenolic hydroxy group.
  • the alkali-soluble resin includes, for example, a copolymer of an epoxy group-containing (meth) acrylate and another radically polymerizable monomer, which is unsaturated in at least a part of the epoxy groups of the copolymer.
  • alkali-soluble resin examples include an acidic group-containing unsaturated monomer component, styrene, methylstyrene, 2-hydroxyethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, and benzyl.
  • Acid group-containing common weight obtained by radical polymerization of at least one monomer component selected from the group consisting of (meth) acrylate, methyl (meth) acrylate, polystyrene macromonomer, polymethyl (meth) acrylate macromonomer and the like. Combined resin and the like can be mentioned.
  • Examples of the acidic group-containing unsaturated monomer component include (meth) acrylic acid, itaconic acid, maleic acid, maleic anhydride, maleic acid monoalkyl ester, citraconic acid, citraconic anhydride, citraconic acid monoalkyl ester, and sulfoethyl.
  • Examples thereof include meta) acrylate, butyl (meth) acrylamide sulfonic acid, and phosphoethyl (meth) acrylate.
  • the alkali-soluble resin may have a carbon-carbon double bond capable of radical polymerization in the side chain.
  • the photocurability of the coloring composition according to the present invention is enhanced, so that the resolution and adhesion can be further improved.
  • Examples of the method for introducing a radically polymerizable carbon-carbon double bond into the side chain include glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, o- (or m-, or p-).
  • a method of reacting a compound such as vinylbenzyl glycidyl ether with the acidic group of the alkali-soluble resin can be mentioned.
  • the weight average molecular weight (Mw) of the alkali-soluble resin is preferably 500 or more, more preferably 1,000 or more, preferably 200,000 or less, and more preferably 100,000 or less.
  • Mw of the alkali-soluble resin is 500 or more, the heat resistance and film strength of the colored layer formed from the coloring composition are good, and when the Mw is 200,000 or less, the alkali developability of this coating film is high. It will be even better.
  • the acid value of the alkali-soluble resin is preferably 10 mgKOH / g or more, more preferably 20 mgKOH / g or more, preferably 300 mgKOH / g or less, and more preferably 200 mgKOH / g or less.
  • the acid value of the alkali-soluble resin is 10 mgKOH / g or more, the alkali developability when the coloring composition is used as a colored layer is further improved, and when it is 300 mgKOH / g or less, the film strength and the like are improved.
  • the amine value of the alkali-soluble resin is preferably less than 10 mgKOH / g.
  • the content of the alkali-soluble resin is preferably 5 parts by mass or more, more preferably 15 parts by mass or more, still more preferably 30 parts by mass or more, and 200 parts by mass with respect to 100 parts by mass of the coloring material.
  • the following is preferable, and more preferably 120 parts by mass or less.
  • the content of the alkali-soluble resin in the coloring composition is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 5% by mass or more, and 70% by mass or less, based on the total solid content of the coloring composition. Is preferable, more preferably 60% by mass or less, still more preferably 50% by mass or less.
  • the polymerizable resin as the polymerizable compound is a linear polymer having a reactive substituent such as a hydroxy group, a carboxy group or an amino group via an isocyanate group, an aldehyde group, an epoxy group or the like (meth).
  • a resin having a crosslinkable group such as an acrylic compound or silicic acid introduced therein is used.
  • a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an ⁇ -olefin-maleic anhydride copolymer is halved with a (meth) acrylic compound having a hydroxy group such as a hydroxyalkyl (meth) acrylate. Eesterated copolymers are also used.
  • Examples of the monomer having one polymerizable unsaturated bond as the polymerizable compound in the molecule include alkyl (meth) acrylates such as methyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate; benzyl.
  • Aralkyl (meth) acrylates such as (meth) acrylates; alkoxyalkyl (meth) acrylates such as butoxyethyl (meth) acrylates; aminoalkyl (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylates; diethylene glycol ethyl ether , (Meta) acrylate of polyalkylene glycol alkyl ether such as triethylene glycol butyl ether, dipropylene glycol methyl ether; (meth) acrylate of polyalkylene glycol aryl ether such as hexaethylene glycol phenyl ether; isobonyl (meth) acrylate; glycerol ( Meta) acrylate; 2-hydroxyethyl (meth) acrylate and the like can be mentioned.
  • Examples of the monomer having two or more polymerizable unsaturated bonds as the polymerizable compound in the molecule include bisphenol A di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,3-butylene glycol di.
  • the content of the polymerizable compound in the coloring composition is preferably 3% by mass or more, more preferably 5% by mass or more, preferably 50% by mass or less, and more preferably 20% by mass, based on the total solid content of the coloring composition. It is less than mass%. If the content of the polymerizable compound is too small, sufficient curability may not be obtained. On the other hand, if the amount of the polymerizable compound is too large, the coloring composition of the present invention tends to have low alkali developability, and background stains, film residues, etc. tend to occur on the substrate or the light-shielding layer in the unexposed portion. is there.
  • thermosetting resin thermoplastic resin
  • thermoplastic resin examples include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, and polyvinyl acetate.
  • Polyurethane resin phenol resin, polyester resin, acrylic resin, alkyd resin, styrene resin, polyamide resin, rubber resin, cyclized rubber, epoxy resin, celluloses, polybutadiene, polyimide resin, benzoguanamine resin, melamine resin, urea resin And so on.
  • the coloring composition preferably contains a photopolymerization initiator. Thereby, the coloring composition can be imparted with radiation sensitivity.
  • the photopolymerization initiator is a compound that generates an active species capable of initiating the polymerization of a cross-linking agent by exposure to radiation such as visible light, ultraviolet rays, far infrared rays, electron beams, and X-rays.
  • photopolymerization initiator examples include thioxanthone-based compounds, acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, O-acyloxime-based compounds, onium salt-based compounds, benzoin-based compounds, benzophenone-based compounds, and ⁇ -diketones. Examples thereof include system compounds, polynuclear quinone compounds, diazo compounds, imide sulfonate compounds, aminoketone compounds and the like.
  • the photopolymerization initiator may be used alone or in combination of two or more.
  • the content of the photopolymerization initiator is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 20% by mass or less in the total amount of the solid matter of the coloring composition. , More preferably 10% by mass or less.
  • the content of the photopolymerization initiator is too small, curing may be insufficient due to exposure, while if it is too large, the formed colored layer tends to easily fall off from the substrate during development.
  • Other compounding agents include sensitizers, thermal polymerization inhibitors, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, plasticizers, organic carboxylic acid compounds, and organic carboxylic acids. Acid anhydrides, pH adjusters, antioxidants other than the phenolic antioxidants, UV absorbers, light stabilizers, preservatives, antifungal agents, anti-aggregation agents, adhesion improvers, development improvers, storage stability Agents and the like can be mentioned.
  • the coloring composition includes a coloring material, a dispersant, a dispersion medium, a phosphite ester, a phenolic antioxidant, a binder resin, a photopolymerization initiator, a photodiffusing agent (precipitated barium sulfate, etc.), if necessary. It can be prepared by mixing other compounding agents. For mixing, for example, a mixing and dispersing machine such as a paint shaker, a bead mill, a ball mill, a dissolver, and a kneader can be used. The coloring composition is preferably filtered after mixing.
  • the method of mixing each material is not particularly limited, and for example, a method of mixing all the materials at once; a colorant, a dispersant, and a dispersion medium are mixed, the colorant is dispersed in advance, and then the colorant is dispersed.
  • a method of mixing other materials in a liquid; a method of mixing a colorant, a dispersant, and a part of other materials to prepare a colorant dispersion base, and then mixing other materials with the colorant dispersion base, etc. can be mentioned. Since the coloring composition has excellent dispersibility and suppresses the generation of formaldehyde, it can be suitably used for a black matrix.
  • the color filter of the present invention includes color pixels that transmit light of the three primary colors of red (R), green (G), and blue (B) on a transparent substrate, and a black matrix formed from the coloring composition. It is a thing.
  • Examples of the method for manufacturing the color filter include the following methods. First, sheets made of thermoplastic resins such as polyester resins, polyolefin resins, polycarbonate resins, and polymethylmethacrylate resins, thermosetting resin sheets such as epoxy resins, unsaturated polyester resins, and poly (meth) acrylic resins, and various glasses.
  • thermoplastic resins such as polyester resins, polyolefin resins, polycarbonate resins, and polymethylmethacrylate resins
  • thermosetting resin sheets such as epoxy resins, unsaturated polyester resins, and poly (meth) acrylic resins
  • the coloring composition for black matrix of the present invention is applied onto a transparent substrate such as, and then prebaked to evaporate the solvent (dispersion medium) to form a coating film.
  • the coating film is exposed to a photomask and then developed with an alkaline developer (an aqueous solution containing an organic solvent or a surfactant and an alkaline compound, etc.) to dissolve and remove the unexposed portion of the coating film. And form a black pattern (black matrix). Then, after post-baking as necessary, the same operation is repeated sequentially for red (R), green (G), and blue (B), so that the pixel arrays of the three primary colors of red, green, and blue are arranged on the substrate. The resulting color filter is obtained.
  • an alkaline developer an aqueous solution containing an organic solvent or a surfactant and an alkaline compound, etc.
  • an appropriate coating method such as a spray method, a roll coating method, a rotary coating method (spin coating method), a slit die coating method, or a bar coating method can be adopted.
  • spin coating method spin coating method
  • slit die coating method a slit die coating method
  • bar coating method it is preferable to adopt the spin coating method and the slit die coating method.
  • a protective film is formed on the pixel pattern thus obtained as needed, and then a transparent conductive film (ITO (indium tin oxide) or the like) is formed by sputtering. After forming the transparent conductive film, a spacer may be further formed to form a color filter.
  • ITO indium tin oxide
  • the color filter of the present invention suppresses the generation of formaldehyde and has high dimensional accuracy and the like, it is suitably used for a color liquid crystal display element, a color image pickup tube element, a color sensor, an organic electroluminescence display element, electronic paper, and the like. Can be done.
  • Each coloring composition was applied onto a glass substrate with a spin coater so as to have a film thickness of 1 ⁇ m, and prebaked at 100 ° C. for 3 minutes. Then, using a mask capable of obtaining a grid pattern having a line width of 25 ⁇ m in which the area ratio of the cured portion to the uncured portion was 20:80, exposure was performed using a high-pressure mercury lamp with a UV integrated light intensity of 400 mJ / cm 2. The coating film obtained by using a 0.05% potassium hydroxide aqueous solution was developed, and the developability was evaluated according to the following evaluation criteria from the time when the coloring composition of the unexposed portion could be removed. A: It can be completely removed within 30 seconds. B: It can be completely removed within 60 seconds over 30 seconds. C: It cannot be completely removed even if it exceeds 60 seconds.
  • Each coloring composition was applied onto a glass substrate with a spin coater so as to have a film thickness of 1 ⁇ m, and prebaked at 100 ° C. for 3 minutes. Then, using a mask capable of obtaining a grid pattern having a line width of 25 ⁇ m in which the area ratio of the cured portion to the uncured portion was 20:80, exposure was performed using a high-pressure mercury lamp with a UV integrated light intensity of 400 mJ / cm 2. The obtained coating film was developed using a 0.05% potassium hydroxide aqueous solution, and the time from the time when the coloring composition of the unexposed portion could be removed to the time when the resist composition of the cured portion was removed was taken.
  • the measurement was performed and the development margin was evaluated according to the following evaluation criteria.
  • Formaldehyde detection amount 0.5 g of the coloring composition was added to a cartridge filled with silica gel impregnated with DNPH (2,4-dinitrophenylhydrazine) (Waters, Sep Pak (registered trademark) DNPH silica plus cartridge (product number: WAT037500)). It was injected and allowed to stand at room temperature for 2 hours. It was washed out with 4 mL of acetonitrile and scalpel-up to 5 mL.
  • DNPH 2,4-dinitrophenylhydrazine
  • the amine value represents the mass of the basic component and the equivalent amount of potassium hydroxide (KOH) per 1 g of solid content.
  • KOH potassium hydroxide
  • the measurement sample was dissolved in tetrahydrofuran, and the obtained solution was neutralized and titrated with a 0.1 mol / L hydrochloric acid / 2-propanol solution using a potentiometric titrator (trade name: GT-06, manufactured by Mitsubishi Chemical Corporation).
  • the amine value (B) was calculated by the following formula with the inflection point of the titration pH curve as the titration end point.
  • the acid value represents the mass of potassium hydroxide required to neutralize the acidic component per 1 g of solid content.
  • the measurement sample was dissolved in tetrahydrofuran, several drops of a phenolphthalein ethanol solution was added as an indicator, and the mixture was neutralized and titrated with a 0.1 mol / L potassium hydroxide / ethanol solution.
  • the acid value (A) was calculated by the following formula.
  • A 56.11 ⁇ Vs ⁇ 0.1 ⁇ f / w
  • Vs Amount of 0.1 mol / L potassium hydroxide / ethanol solution required for titration (mL)
  • f Titer of 0.1 mol / L potassium hydroxide / ethanol solution
  • Pigment dispersion base Nos. 1-12, 14-16 Various materials were mixed all at once so as to have the composition shown in Table 1, and the meat was kneaded with a bead mill for 24 hours to prepare a pigment dispersion base.
  • Pigment Dispersion Base No. 13 Each material excluding the phosphite ester shown in Table 1 was mixed all at once and kneaded with a bead mill for a whole day and night, and then the phosphite ester was added to the kneaded meat to prepare a pigment dispersion base.
  • Pigment dispersion base No. No. 13 had good dispersion stability.
  • Tables 1 and 2 The materials used in Tables 1 and 2 are as follows. SB250: Carbon black (manufactured by Cabot, trade name "Special Black 250") PY185: C.I. I. Pigment Yellow 185 PV29: C.I. I. Pigment Violet 29 PB60: C.I. I.
  • Pigment Blue 60 Dispersant 1 Amino group-containing polyurethane resin type dispersant (acid value 0 mgKOH / g, amine value 36 mgKOH / g)
  • Dispersant 2 Amino group-containing polyurethane resin type dispersant (acid value 0 mgKOH / g, amine value 45 mgKOH / g)
  • Dispersant 3 Amino group-containing (meth) acrylic resin type dispersant (acid value 0 mgKOH / g, amine value 63 mgKOH / g)
  • Dispersant 4 Amino group-containing polyester amide resin type dispersant (acid value 17 mgKOH / g, amine value 10 mgKOH / g) Phthalocyanine-based (pigment derivative having a copper phthalocyanine-based pigment skeleton, manufactured by Lubrizol, trade name "Solspace (registered trademark) 5000”) Alkali-soluble resin: benzyl methacrylate
  • each pigment dispersion base and other materials were uniformly mixed so as to have the compositions shown in Tables 3 and 4. Then, each colored composition was obtained by filtering through a filter having a pore size of 3 ⁇ m.
  • Coloring composition No. 1 to 13 and 16 are cases where a colorant, a dispersant, a dispersion medium and a specific phosphite ester are contained. These coloring compositions No. In Nos. 1 to 13 and 16, the dispersion stability, developability, and development margin were all good, and the amount of formaldehyde detected was reduced to 2 ppm or less. In particular, the coloring composition No. 1 containing a phenolic antioxidant. 1 to 13 had more excellent dispersion stability. In addition, the coloring composition No. Although the timing of addition of the phosphite ester is different between 2 and 13, the amount of formaldehyde detected is further reduced when the phosphite ester is added when the colorant and the dispersant are mixed. It was.
  • the present invention includes the following embodiments.
  • (Embodiment 1) Contains colorants, dispersants, dispersion media and phosphite esters, A coloring composition for a black matrix, wherein the phosphite ester is a compound represented by the general formula (5).
  • R 51 represents an alkyl group having 1 to 20 carbon atoms.
  • R 52 and R 53 each independently represent a hydrocarbon group.
  • R 52 and R 53 may be coupled to each other to form a cyclic structure.
  • the compound represented by the general formula (5) may be bonded at R 52 or R 53 to form a dimer or a trimer.
  • R 61 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 62 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 63 represents a group in which any one or more carbon atoms of the hydrocarbon group having 2 to 20 carbon atoms is substituted with an ester group or an ether group, or a hydrocarbon group having 1 to 20 carbon atoms.
  • n represents a number from 1 to 6.
  • the carbon atom bonded to the benzene ring of R 61 is a primary to tertiary carbon atom.
  • a transparent substrate and a black matrix formed on the transparent substrate are provided.
  • a color filter characterized in that the black matrix is formed from the coloring composition for black matrix according to any one of aspects 1 to 13.

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Abstract

Le problème décrit par la présente invention est de fournir une composition colorante qui est destinée à une matrice noire et qui présente une performance de dispersion élevée d'un matériau colorant et une petite quantité de formaldéhyde générée dans le temps. La solution selon l'invention porte sur une composition colorante destinée à une matrice noire et caractérisée en ce qu'elle contient un matériau colorant, un dispersant, un milieu de dispersion et un phosphite, le phosphite étant un composé représenté par la formule générale (5). [Dans la formule générale (5), R51 représente un groupe alkyle en C1-C20. R52 et R53 représentent chacun indépendamment un groupe hydrocarbure. R52 et R53 peuvent être liés l'un à l'autre pour former une structure cyclique. Les composés représentés par la formule générale (5) peuvent être liés l'un à l'autre au niveau de R52 ou R53 pour former un dimère ou un trimère.]
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