WO2016199778A1 - 色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタの製造方法、液晶表示装置の製造方法、及び発光表示装置の製造方法 - Google Patents

色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタの製造方法、液晶表示装置の製造方法、及び発光表示装置の製造方法 Download PDF

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WO2016199778A1
WO2016199778A1 PCT/JP2016/066961 JP2016066961W WO2016199778A1 WO 2016199778 A1 WO2016199778 A1 WO 2016199778A1 JP 2016066961 W JP2016066961 W JP 2016066961W WO 2016199778 A1 WO2016199778 A1 WO 2016199778A1
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group
general formula
mass
structural unit
color filter
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PCT/JP2016/066961
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English (en)
French (fr)
Japanese (ja)
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教弘 小倉
智基 村田
史泰 村上
政人 岡田
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大日本印刷株式会社
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    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces

Definitions

  • the present disclosure relates to a color material dispersion, a colored resin composition for a color filter, a color filter manufacturing method, a liquid crystal display device manufacturing method, and a light emitting display device manufacturing method.
  • Color filters are used in these liquid crystal display devices and organic light emitting display devices.
  • a backlight is used as a light source, the amount of light is controlled by electrically driving the liquid crystal, and color expression is performed by the light passing through a color filter. Therefore, a color filter must be present in the color representation of a liquid crystal television and plays a major role in determining the performance of the display.
  • a color filter is used for the white light emitting organic light emitting element, a color image is formed as in the liquid crystal display device.
  • An image display device including a color filter affects the design and performance of a mobile terminal in order to be directly linked to the usable time and charging frequency of the mobile terminal.
  • the color filter is generally formed on a transparent substrate, a transparent substrate, and a colored layer formed of three primary colors of red, green, and blue, and a transparent substrate so as to partition each colored pattern. And a light shielding portion.
  • a method for forming such a colored layer a method is known in which a resin composition in which a curable binder component or the like is added to a color material dispersion in which a color material is dispersed is applied to a substrate and cured.
  • the color material dispersion is required to have dispersibility and dispersion stability of the color material in order to stably obtain a high-contrast colored layer.
  • the colored layer obtained from such a colorant dispersion may have various resistances in the production process inferior to those of ordinary pigments.
  • improvement in heat resistance in the heating process and resistance to a solvent (N-methylpyrrolidone: NMP) in the alignment film forming process is required from the manufacturing process.
  • Patent Document 1 discloses at least one selected from the group consisting of dyes and lake pigments as a coloring composition that is exhibited without losing the excellent chromaticity characteristics of the dyes and lake pigments even after a high-temperature heating step.
  • a coloring composition characterized in that it contains a crosslinking agent characterized in that it contains a crosslinking agent.
  • the technique of Patent Document 1 has a problem that the heat resistance of the lake pigment is insufficient and the NMP resistance is poor as shown in a comparative example described later.
  • Patent Document 2 discloses a pigment dispersant which is a copolymer containing a monomer having a specific phosphate group and a monomer having a specific polycaprolactone skeleton as a copolymerization component.
  • the dispersant is a pigment dispersant having high dispersion stability, and is a pigment-dispersed resist dispersant effective in improving resist characteristics.
  • the photosensitive resin composition described in Patent Document 2 has poor dispersibility and storage stability, and has a problem that contrast is lowered when a colored layer is formed after long-term storage.
  • the side chain of the pigment dispersant has a polycaprolactone skeleton as a main component, there is a problem that the heat resistance and NMP resistance of the colored cured film are poor.
  • Patent Document 3 includes C.I. I. A coloring composition containing Pigment Red 81: 2 pigment, an organic solvent having a solubility parameter of 9.0 or less, and a pigment carrier made of a transparent resin or the like is disclosed. According to Patent Document 3, C.I. I. Even if Pigment Red 81: 2 is used, it is said that high transparency and dispersion stability can be obtained. However, the coloring composition described in Patent Document 3 merely selects a low-polar organic solvent that does not dissolve the pigment, and has insufficient dispersibility for use as a color filter. There is also a problem that the solvent resistance of the cured coating film is poor.
  • Patent Document 4 discloses C.I. I. As a composition that is excellent in storage stability even when Pigment Green 58 is used and can suppress a decrease in contrast, C.I. I.
  • the solubility parameter is 18.0 (J / cm 3 ) 1/2 or less (ie, A colored coating liquid composition for a color filter is disclosed in which at least one organic solvent of 8.8 (cal / cm 3 ) 1 ⁇ 2 or less occupies 90% by mass or more of the total organic solvent.
  • the colored coating liquid composition for color filters described in Patent Document 4 merely selects an organic solvent in which the pigment does not dissolve, and has a problem that the solvent resistance of the cured coating film is also poor.
  • Embodiments of the present disclosure are excellent in dispersibility and storage stability, have a high contrast even after long-term storage, a colorant dispersion that can form a coating film excellent in heat resistance and solvent resistance, and dispersibility And a color resin composition for color filters capable of forming a colored layer having excellent storage stability, high contrast even after long-term storage, and excellent heat resistance and solvent resistance, and a method for producing the same, and high contrast
  • Another object of the present invention is to provide a method for producing a color filter excellent in heat resistance and solvent resistance, a method for producing a liquid crystal display device, and a method for producing an organic light emitting display device.
  • One embodiment of the present disclosure contains (A) a color material, (B) a dispersant, and (C) a solvent, and the (B) dispersant is represented by the following general formula (I).
  • a polymer having one or more units selected from structural units represented by the following general formula (I ′), and the solvent (C) has an SP value of 8.6 (cal / cm 3 ) 1 / 2 to 9.4 (cal / cm 3 ) 1/2 or less solvent (1), and SP value is 7.8 (cal / cm 3 ) 1/2 or more to 8.6 (cal / cm 3 ) 1 /
  • a coloring material dispersion containing less than 2 solvent (2).
  • L 1 is a direct bond or a divalent linking group
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a hydroxyl group, a hydrocarbon group, — [ A monovalent group represented by CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 , — [(CH 2 ) y1 —O] z1 —R 5 , or —O—R 6
  • R 6 is a hydrocarbon group, — [CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 , — [(CH 2 ) y1 —O] z1 —R 5 , —C (R 7 )
  • It is a monovalent group represented by (R 8 ) —C (R 9 ) (R 10 ) —OH or —CH 2 —C (R 11 ) (R 12 ) —CH 2 —
  • R 3 and R 4 are each independently a hydrogen atom or a methyl group
  • R 5 is a hydrogen atom, a hydrocarbon group, —CHO, —CH 2 CHO, —CO—CH ⁇ CH 2 , —CO—C ( CH 3 ) ⁇ CH 2 or a monovalent group represented by —CH 2 COOR 13
  • R 13 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently a hydrogen atom, a hydrocarbon group, or a hydrocarbon group having one or more selected from an ether bond and an ester bond. And R 7 and R 9 may combine with each other to form a ring structure.
  • the cyclic structure may further have a substituent R 14 , and R 14 is a hydrocarbon group, or a carbonization having at least one selected from an ether bond and an ester bond. It is a hydrogen group.
  • the hydrocarbon group may have a substituent.
  • X + represents an organic cation.
  • x1 represents an integer of 1 to 18, y1 represents an integer of 1 to 5, and
  • z1 represents an integer of 1 to 18.
  • 1 embodiment of this indication provides the coloring resin composition for color filters containing the color material dispersion concerning the above-mentioned embodiment, and (D) binder ingredient.
  • the (B) dispersant is one or more selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′).
  • a structural unit represented by the following general formula (II), or a structural unit represented by the general formula (I) and the general formula (I ′) A colorant dispersion and a colored resin composition for a color filter, which is a block copolymer having at least one selected from the structural units represented, and a structural unit represented by the following general formula (III): provide.
  • L 2 is a direct bond or a divalent linking group
  • R 21 is a hydrogen atom or a methyl group
  • Polymer is a polymer chain having a structural unit represented by the following General Formula (IV) Represents.
  • R 22 is a hydrogen atom or a methyl group
  • R 23 is a hydrocarbon group, — [CH (R 24 ) —CH (R 25 ) —O] x2 —R 26 , — [(CH 2 ) y2 —O] z2 —R 26 , — [CO— (CH 2 ) y2 —O] z2 —R 26 , —CO—O—R 26 ′ or —O—CO—R 26 ′′
  • R 24 and R 25 are each independently a hydrogen atom or a methyl group
  • R 26 is a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO or —CH 2 COOR 27
  • R 26 ′ is a hydrocarbon group, — [CH (R 24 ) —CH (R 25 ) —O] x2 ′ —R 26 , — [(CH 2 ) y2 ′ —O] z2
  • R 31 is a hydrogen atom or a methyl group
  • R 32 is a hydrocarbon group, — [CH (R 33 ) —CH (R 34 ) —O] x3 —R 35 , — [( CH 2 ) y 3 —O] z 3 —R 35 , — [CO— (CH 2 ) y 3 —O] z 3 —R 35 , —CO—O—R 36 or —O—CO—R 37
  • the groups R 33 and R 34 are each independently a hydrogen atom or a methyl group
  • R 35 is a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO or —CH 2 COOR 38
  • R 36 represents a hydrocarbon group, — [CH (R 33 ) —CH (R 34 ) —O] x4 —R 35 , — [(CH 2 ) y4 —O] z4 —R 35
  • R 2 in the general formula (I) and the general formula (I ′) is a hydrocarbon group, — [CH (R 3 ) —CH (R 4 ) —O] x1 —
  • a colorant dispersion which is a monovalent group represented by R 5 or — [(CH 2 ) y1 —O] z1 —R 5 , and a colored resin composition for a color filter.
  • the dispersant (B) is a reaction product of a polymer having at least one of an epoxy group and a cyclic ether group in a side chain and an acidic phosphorus compound, and the acidic phosphorus compound group
  • a colorant dispersion and a color resin composition for a color filter in which at least a part of the polymer is a polymer which may form a salt.
  • the color material (A) includes at least one selected from the group consisting of a triarylmethane color material and a xanthene color material, and a color material dispersion liquid and a color A colored resin composition for a filter is provided.
  • One embodiment of the present disclosure provides a color material dispersion and a color resin composition for a color filter, in which the color material (A) includes a metal lake color material of a basic dye.
  • the color material (A) includes a color material (A-1) represented by the following general formula (VI), and a color resin composition for a color filter I will provide a.
  • A is an a-valent organic group in which the carbon atom directly bonded to N has no ⁇ bond, and the organic group is saturated aliphatic carbonized at least at the terminal directly bonded to N.
  • B c- represents a polyvalent polyvalent R i , R ii , R iii , R iv , and R v each independently represent a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group R ii and R iii , R iv and R v may combine to form a ring structure
  • Ar 1 represents a divalent aromatic group which may have a substituent.
  • R i to R v and Ar 1 may be the same or different.
  • a and c represent an integer of 2 or more
  • b and d represent an integer of 1 or more.
  • e is 0 or 1, and when e is 0, there is no bond.
  • a plurality of e may be the same or different.
  • One embodiment of the present disclosure is a method of manufacturing a color filter including at least a transparent substrate and a colored layer provided on the transparent substrate, Provided is a method for producing a color filter, comprising a step of forming at least one of colored layers by curing the colored resin composition for a color filter according to the embodiment on a transparent substrate.
  • One embodiment of the present disclosure includes a step of manufacturing a color filter by the method for manufacturing a color filter according to the embodiment, and a step of assembling the manufactured color filter and a liquid crystal driving substrate to face each other.
  • a method for manufacturing a liquid crystal display device is provided.
  • the manufacturing method of the color filter according to the embodiment includes a step of manufacturing a color filter and a surface of the substrate having a light emitting layer on the side having the light emitting layer.
  • a method for manufacturing a light emitting display device which includes a step of disposing a color filter.
  • a colorant dispersion that is excellent in dispersibility and storage stability can form a coating film that has high contrast and excellent heat resistance and solvent resistance even after long-term storage
  • Colored resin composition for color filter which is excellent in dispersibility and storage stability, can form a colored layer with high contrast and excellent heat resistance and solvent resistance even after long-term storage, and its production method, high It is possible to provide a color filter manufacturing method, a liquid crystal display device manufacturing method, and an organic light emitting display device manufacturing method that are excellent in heat resistance and solvent resistance in contrast.
  • FIG. 1 is a cross-sectional view schematically illustrating an example of a color filter obtained by a method for manufacturing a color filter according to an embodiment of the present disclosure.
  • FIG. 2 is a schematic diagram illustrating an example of a liquid crystal display device obtained by a method for manufacturing a liquid crystal display device according to an embodiment of the present disclosure.
  • FIG. 3 is a schematic diagram illustrating an example of a light-emitting display device obtained by a method for manufacturing a light-emitting display device according to an embodiment of the present disclosure.
  • light includes electromagnetic waves having wavelengths in the visible and invisible regions, and further includes radiation, and the radiation includes, for example, microwaves and electron beams. Specifically, it means an electromagnetic wave having a wavelength of 5 ⁇ m or less and an electron beam.
  • (meth) acryl represents each of acryl and methacryl
  • (meth) acrylate represents each of acrylate and methacrylate.
  • an organic group refers to a group having one or more carbon atoms.
  • Color Material Dispersion contains (A) a color material, (B) a dispersant, and (C) a solvent. It is a polymer having at least one selected from the structural unit represented by the formula (I) and the structural unit represented by the following general formula (I ′), and the solvent (C) has an SP value of 8 .6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less solvent (1) and SP value of 7.8 (cal / cm 3 ) 1/2 or more It contains 6 (cal / cm 3 ) 1/2 or less of the solvent (2).
  • L 1 is a direct bond or a divalent linking group
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a hydroxyl group, a hydrocarbon group, — [ A monovalent group represented by CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 , — [(CH 2 ) y1 —O] z1 —R 5 , or —O—R 6
  • R 6 is a hydrocarbon group, — [CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 , — [(CH 2 ) y1 —O] z1 —R 5 , —C (R 7 )
  • It is a monovalent group represented by (R 8 ) —C (R 9 ) (R 10 ) —OH or —CH 2 —C (R 11 ) (R 12 ) —CH 2 —
  • R 3 and R 4 are each independently a hydrogen atom or a methyl group
  • R 5 is a hydrogen atom, a hydrocarbon group, —CHO, —CH 2 CHO, —CO—CH ⁇ CH 2 , —CO—C ( CH 3 ) ⁇ CH 2 or a monovalent group represented by —CH 2 COOR 13
  • R 13 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently a hydrogen atom, a hydrocarbon group, or a hydrocarbon group having one or more selected from an ether bond and an ester bond. And R 7 and R 9 may combine with each other to form a ring structure.
  • the cyclic structure may further have a substituent R 14 , and R 14 is a hydrocarbon group, or a carbonization having at least one selected from an ether bond and an ester bond. It is a hydrogen group.
  • the hydrocarbon group may have a substituent.
  • X + represents an organic cation.
  • x1 represents an integer of 1 to 18, y1 represents an integer of 1 to 5, and
  • z1 represents an integer of 1 to 18.
  • the colorant dispersion according to the embodiment of the present disclosure is excellent in dispersibility and storage stability, and can form a coating film having high contrast and excellent heat resistance even after long-term storage.
  • a colored resin composition for a color filter can be obtained.
  • the action that exerts the above effects by the specific combination is estimated as follows.
  • the colorant dispersion according to the embodiment of the present disclosure is a dispersant selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′).
  • the dispersant is an ethylenically unsaturated monomer polymer
  • the skeleton has higher heat resistance than a polyether-based or polyester-based polymer, and a plurality of acidic phosphorus compound groups (- P ( ⁇ O) (— R 2 ) (OH)) and a salt thereof (—P ( ⁇ O) (— R 2 ) (O ⁇ X + )) have an adsorptive power to the surface of the finely divided color material. Presumed to be strong. After the colored layer was formed, after the surrounding solvent content decreased, the interaction between the acidic phosphorus compound group and the colorant was particularly strong, and it was estimated that the heat resistance was improved as a result.
  • the surface of the colorant is covered with at least one of an acidic phosphorus compound group and a salt thereof, attack on the pigment skeleton of the lake pigment by active oxygen such as peroxy radical (hydrogen abstraction or substitution reaction) It is speculated that color material deterioration (oxidation deterioration) is suppressed.
  • the dispersant used in the present embodiment can suppress the sublimation of the metal lake color material of the xanthene-based basic dye that may sublimate during high temperature heating during the production of the color filter.
  • the particularly high effect of the basic dye metal lake colorant is presumed to be due to the particularly strong adsorption of acidic phosphorus compound groups and salts thereof on the cation moiety of the basic dye.
  • the colorant dispersion using the above dispersant has poor storage stability, and the contrast of the obtained colored layer may be lowered with time.
  • the inventors of the present invention have found that when a solvent having a relatively high polarity is used, the solvent having a relatively high polarity is likely to interact (solvate) with the acidic phosphorus structure. It was found that the adsorptive power to the surface of the material decreased, the dispersibility decreased with time, and the storage stability deteriorated.
  • the colorant dispersion according to an embodiment of the present disclosure has a relatively high SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less as a solvent.
  • the colorant dispersion according to the embodiment of the present disclosure is selected from the structural unit represented by the general formula (I) and the structural unit represented by the following general formula (I ′).
  • a polymer having a seed or more is used as a dispersant, a solvent (1) having an SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less, and an SP value Dispersibility by dispersing the colorant in a mixed solvent in which a solvent (2) having a ratio of 7.8 (cal / cm 3 ) 1/2 or more and less than 8.6 (cal / cm 3 ) 1/2 is combined
  • the storage stability is excellent, and even when the colored layer is produced after long-term storage, a decrease in contrast is suppressed.
  • the colored layer obtained using the color material dispersion according to the embodiment of the present disclosure is excellent in heat resistance. As a result, it is possible to reduce the amount of color material added to achieve a desired chromaticity, and to increase the degree of freedom in designing a color filter, for example, by thinning the colored layer.
  • the color material dispersion according to an embodiment of the present disclosure contains at least a color material, a dispersant, and a solvent, and further contains other components as necessary within a range where the effect is not impaired. You may do it.
  • each component of such a color material dispersion will be described in detail in the order of (B) dispersant, (C) solvent, and (A) color material.
  • the (B) dispersant is a heavy component having at least one selected from the structural unit represented by the following general formula (I) and the structural unit represented by the following general formula (I ′). Coalescence is used.
  • One or more selected from the structural unit represented by the following general formula (I) and the structural unit represented by the following general formula (I ′) each have a structural unit obtained by polymerizing an ethylenically unsaturated monomer. It is a polymer, and the polymer is an ethylenically unsaturated monomer polymer copolymerizable with other ethylenically unsaturated monomers.
  • L 1 is a direct bond or a divalent linking group.
  • the direct bond of L 1 means that the phosphorus atom is directly bonded to the carbon atom of the main chain skeleton without a linking group.
  • the divalent linking group in L 1 is not particularly limited as long as it can link the carbon atom of the main chain skeleton and the phosphorus atom.
  • Examples of the divalent linking group for L 1 include a linear, branched or cyclic alkylene group, a linear, branched or cyclic alkylene group having a hydroxyl group, an arylene group, a —CONH— group, a —COO— group, And —NHCOO— group, ether group (—O— group), thioether group (—S— group), and combinations thereof.
  • the direction of bonding of the divalent linking group is arbitrary. That is, when the divalent linking group includes —CONH—, —CO may be on the carbon atom side of the main chain and —NH may be on the phosphorus atom side of the side chain, and on the contrary, —NH may be on the main chain. On the carbon atom side, —CO may be on the phosphorus atom side of the side chain.
  • L 1 in formulas (I) and (I ′) is preferably a divalent linking group containing a —CONH— group or a —COO— group.
  • L 1 is a divalent linking group containing a —COO— group
  • the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) are each represented by the following formula (I And a structure represented by the following formula (I′-1).
  • R 1 and R 2 are the same as in general formula (I) and general formula (I ′), and X + represents general formula L 1 ′ is the same as (I ′), and L 1 ′ is an alkylene group having 1 to 8 carbon atoms which may have a hydroxyl group, — [CH (R a ) —CH (R b ) — O] x- , or-[(CH 2 ) y -O] z- (CH 2 ) y -O-,-[CH (R c )] w -O-, and R a , R b and R c is each independently a hydrogen atom, a methyl group, or a hydroxyl group, x is an integer of 1 to 18, y is an integer of 1 to 5, z is an integer of 1 to 18, and w is 1 to 18. Represents an integer.)
  • the alkylene group having 1 to 8 carbon atoms in L 1 ′ may be linear, branched or cyclic, and examples thereof include a methylene group, an ethylene group, a trimethylene group, a propylene group, There are various butylene groups, various pentylene groups, various hexylene groups, various octylene groups, etc., and some hydrogens may be substituted with hydroxyl groups.
  • x is an integer of 1 to 18, preferably an integer of 1 to 4, more preferably an integer of 1 to 2, and y is an integer of 1 to 5, preferably 1 to 4 and more preferably.
  • z is an integer of 1 or more and 18 or less, preferably an integer of 1 or more and 4 or less, more preferably an integer of 1 or more and 2 or less.
  • w is an integer of 1 to 18, preferably an integer of 1 to 4.
  • L 1 in the general formula (I) and the general formula (I ′) include, for example, —COO—CH 2 CH (OH) CH 2 —O—, —COO—CH 2 CH 2 —O—.
  • Examples include, but are not limited to, CH 2 CH (OH) CH 2 —O—, —COO—CH 2 C (CH 2 CH 3 ) (CH 2 OH) CH 2 —O—, and the like.
  • Examples of the hydrocarbon group for R 2 include an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, and an aryl group.
  • the alkyl group having 1 to 18 carbon atoms may be linear, branched or cyclic, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n- Examples thereof include a butyl group, a cyclopentyl group, a cyclohexyl group, a bornyl group, an isobornyl group, a dicyclopentanyl group, an adamantyl group, and a lower alkyl group-substituted adamantyl group.
  • the alkenyl group having 2 to 18 carbon atoms may be linear, branched or cyclic.
  • Examples of such an alkenyl group include a vinyl group, an allyl group, and a propenyl group.
  • the position of the double bond of the alkenyl group is not limited, but from the viewpoint of the reactivity of the polymer obtained, it is preferable that there is a double bond at the terminal of the alkenyl group.
  • the aryl group include a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, and a xylyl group, and may further have a substituent.
  • the number of carbon atoms in the aryl group is preferably 6 or more and 24 or less, and more preferably 6 or more and 12 or less.
  • a benzyl group, a phenethyl group, a naphthylmethyl group, a biphenylmethyl group, etc. are mentioned, Furthermore, you may have a substituent.
  • the number of carbon atoms in the aralkyl group is preferably 7 or more and 20 or less, and more preferably 7 or more and 14 or less.
  • the alkyl group or alkenyl group may have a substituent, and examples of the substituent include halogen atoms such as F, Cl, and Br, and nitro groups.
  • examples of the substituent of the aromatic ring such as the aryl group and the aralkyl group include linear and branched alkyl groups having 1 to 4 carbon atoms, alkenyl groups, nitro groups, halogen atoms, and the like. Can be mentioned. The preferable number of carbon atoms does not include the number of carbon atoms of the substituent.
  • x1 is the same as x
  • y1 is the same as y
  • z1 is the same as z.
  • Examples of the hydrocarbon group for R 5 to R 12 include the same hydrocarbon groups as those described above for R 2 .
  • the hydrocarbon group having at least one selected from an ether bond and an ester bond in R 7 , R 8 , R 9 , R 10 , R 11 and R 12 is —R′—O—R ′′, —R “— (C ⁇ O) —O—R ′′, or —R′—O— (C ⁇ O) —R ′′ (R ′ and R ′′ represent a hydrocarbon group, or an ether bond and an ester of a hydrocarbon group.
  • One group may have two or more ether bonds and ester bonds.
  • Examples of the monovalent hydrocarbon group include an alkyl group, an alkenyl group, an aralkyl group, and an aryl group.
  • Examples of the divalent hydrocarbon group include an alkylene group, an alkenylene group, an arylene group, and combinations thereof. The group of is mentioned.
  • the number of carbon atoms forming the ring structure is preferably 5 or more and 8 or less, and is 6, that is, a 6-membered ring. Is more preferable, and it is preferable to form a cyclohexane ring.
  • the hydrocarbon group in the substituent R 14 or a hydrocarbon group having at least one selected from an ether bond and an ester bond is the above-mentioned R 7 , R 8 , R 9 , R 10 , R 11 and R 12 . Can be similar.
  • R 2 is a hydroxyl group, a hydrocarbon group, — [CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 , — [ It is preferably a monovalent group represented by (CH 2 ) y1 —O] z1 —R 5 or —O—R 6 , and has a hydroxyl group, a methyl group, an ethyl group, a vinyl group, or a substituent.
  • R 2 represents a hydrocarbon group, — [CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 , or — [(CH 2 ) y1 —O ] it is preferably a monovalent group represented by z1 -R 5.
  • R 2 has a structure in which a carbon atom is directly bonded to a phosphorus atom, it is presumed that a resin layer excellent in alkali resistance can be formed because it is hardly hydrolyzed.
  • R 2 is a methyl group, an ethyl group, an aryl group or an aralkyl group which may have a substituent, a vinyl group, an allyl group, — [CH (R 3 ) —CH (R 4 ) —O] x1 —R 5 or a monovalent group represented by — [(CH 2 ) y1 —O] z1 —R 5 , R 3 and R 4 are each independently a hydrogen atom or a methyl group, and R 5 is —CO It is preferable that —CH ⁇ CH 2 or —CO—C (CH 3 ) ⁇ CH 2 is excellent in alkali resistance and excellent in dispersibility and dispersion stability of dispersed particles. Among these, R 2 is more preferably an aryl group which may have a substituent from the viewpoint of dispersibility.
  • X + represents an organic cation.
  • An organic cation refers to one containing a carbon atom in the cation moiety.
  • Examples of the organic cation include imidazolium cation, pyridinium cation, aminidium cation, piperidinium cation, pyrrolidinium cation, ammonium cation such as tetraalkylammonium cation and trialkylammonium cation, and sulfonium cation such as trialkylsulfonium cation.
  • phosphonium cations such as tetraalkylphosphonium cations.
  • a protonated nitrogen-containing organic cation is preferable from the viewpoint of dispersibility and alkali developability.
  • an organic cation has an ethylenically unsaturated double bond, it is preferable from the point which can provide sclerosis
  • the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) may be contained alone in the polymer. Two or more kinds may be included.
  • the dispersant may contain both the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′).
  • both of the structural units are included, there is no particular limitation as long as good dispersibility and dispersion stability are exhibited, and the ratio of the number of structural units represented by the general formula (I ′) is: It is preferably 0 to 50 mol% with respect to the total number of structural units of the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′).
  • the method for synthesizing the polymer having at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) is not particularly limited.
  • a salt containing an organic cation is further produced after the production of the polymer having the structural unit represented by the general formula (I).
  • a salt is formed between the acidic phosphorus compound group of the structural unit represented by the general formula (I) and the organic cation by adding a forming agent, heating as necessary, and stirring.
  • a method of forming the structural unit represented by the general formula (I ′) is preferable.
  • the (B) dispersant is a reaction product of a polymer having at least one of an epoxy group and a cyclic ether group in the side chain and an acidic phosphorus compound, and at least a part of the acidic phosphorus compound group is a salt. It is preferable that it is a polymer which may form. What is necessary is just to select suitably as said salt formation agent according to the organic cation to introduce
  • the addition amount of the salt forming agent only needs to exhibit good dispersibility and dispersion stability, and may be appropriately adjusted according to the proportion of the structural unit to be introduced.
  • the salt forming agent is generally represented by the general formula (I). It is about 0.05 mol equivalent or more and 1.00 mol equivalent or less, preferably 0.3 mol equivalent or more and 0.5 mol equivalent or less with respect to the phosphorus site contained in the structural unit. If necessary, other monomers can also be used to produce a copolymer using a known polymerization means.
  • the (B) dispersant further has a solvent affinity site from the viewpoint of dispersibility.
  • a dispersant (B) among them, one or more selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), It is a graft copolymer having a structural unit represented by the general formula (II), or is represented by the structural unit represented by the general formula (I) and the general formula (I ′).
  • a block copolymer having at least one selected from structural units and a structural unit represented by the following general formula (III) is excellent in dispersibility and storage stability, and after long-term storage. Is preferable from the viewpoint of forming a high-contrast coating film.
  • L 2 is a direct bond or a divalent linking group
  • R 21 is a hydrogen atom or a methyl group
  • Polymer is a polymer chain having a structural unit represented by the following General Formula (IV) Represents.
  • R 22 is a hydrogen atom or a methyl group
  • R 23 is a hydrocarbon group, — [CH (R 24 ) —CH (R 25 ) —O] x2 —R 26 , — [(CH 2 ) y2 —O] z2 —R 26 , — [CO— (CH 2 ) y2 —O] z2 —R 26 , —CO—O—R 26 ′ or —O—CO—R 26 ′′
  • R 24 and R 25 are each independently a hydrogen atom or a methyl group
  • R 26 is a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO or —CH 2 COOR 27
  • R 26 ′ is a hydrocarbon group, — [CH (R 24 ) —CH (R 25 ) —O] x2 ′ —R 26 , — [(CH 2 ) y2 ′ —O] z2
  • R 31 is a hydrogen atom or a methyl group
  • R 32 is a hydrocarbon group, — [CH (R 33 ) —CH (R 34 ) —O] x3 —R 35 , — [( CH 2 ) y 3 —O] z 3 —R 35 , — [CO— (CH 2 ) y 3 —O] z 3 —R 35 , —CO—O—R 36 or —O—CO—R 37
  • the groups R 33 and R 34 are each independently a hydrogen atom or a methyl group
  • R 35 is a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO or —CH 2 COOR 38
  • R 36 represents a hydrocarbon group, — [CH (R 33 ) —CH (R 34 ) —O] x4 —R 35 , — [(CH 2 ) y4 —O] z4 —R 35
  • the preferred graft copolymer as a dispersant is one or more selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), And a structural unit represented by the general formula (II).
  • the graft copolymer will be described.
  • the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) are as described above. Omitted.
  • L 2 is a direct bond or a divalent linking group.
  • the divalent linking group in L 2 is not particularly limited as long as it can link a carbon atom derived from an ethylenically unsaturated double bond and a polymer chain.
  • Examples of the divalent linking group for L 2 include the same divalent linking groups as those described above for L 1 .
  • Polymer represents a polymer chain having a structural unit represented by the general formula (IV).
  • R 31 is a hydrogen atom or a methyl group
  • R 32 is a hydrocarbon group, — [CH (R 33 ) —CH (R 34 ) —O] x3 —R 35 , — [(CH 2 ) Y3 —O] z3 —R 35 , — [CO— (CH 2 ) y3 —O] z3 —R 35 , —CO—O—R 36 or —O—CO—R 37 is there.
  • the hydrocarbon group for R 32 is preferably an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aralkyl group, or an aryl group. These include, for example, the same ones as R 2 described above.
  • R 35 is preferably a hydrogen atom or a monovalent group represented by an alkyl group having 1 to 18 carbon atoms, an aralkyl group, an aryl group, —CHO, —CH 2 CHO or —CH 2 COOR 38.
  • R 36 represents an alkyl group having 1 to 18 carbon atoms, an aralkyl group, an aryl group, — [CH (R 33 ) —CH (R 34 ) —O] x4 —R 35 , — [(CH 2 ) y4 —O] z4 —R 35 , a monovalent group represented by — [CO— (CH 2 ) y4 —O] z4 —R 35 is preferable.
  • R 37 represents an alkyl group having 1 to 18 carbon atoms
  • R 38 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Examples of the alkyl group, aralkyl group, and aryl group having 1 to 18 carbon atoms in R 35 and R 36 are the same as those in R 2 described above.
  • Examples of the alkyl group in R 37 and R 38 are the same as those in R 2 described above.
  • R 35 , R 36 , R 37 and R 38 are groups having an aromatic ring, the aromatic ring may further have a substituent.
  • substituents examples include linear, branched, and cyclic alkyl groups having 1 to 5 carbon atoms, as well as halogen atoms such as alkenyl groups, nitro groups, F, Cl, and Br. It is done. The preferable number of carbon atoms does not include the number of carbon atoms of the substituent.
  • x3 and x4 are the same as x
  • y3 and y4 are the same as y
  • z3 and z4 are the same as z.
  • R 32 , R 35 , R 36 , R 37 and R 38 are within a range not impeding the dispersion performance of the graft copolymer, and further, an alkoxy group, a hydroxyl group, a carboxyl group, an amino group, an epoxy group, It may be substituted with a substituent such as an isocyanate group or a hydrogen bond-forming group. Moreover, after synthesizing a graft copolymer having these substituents, a compound having a functional group that reacts with the substituent and a polymerizable group may be reacted to add a polymerizable group.
  • adding a polymerizable group by reacting a graft copolymer having a carboxyl group with glycidyl (meth) acrylate, or reacting a graft copolymer having an isocyanate group with hydroxyethyl (meth) acrylate.
  • a polymerizable group by reacting a graft copolymer having a carboxyl group with glycidyl (meth) acrylate, or reacting a graft copolymer having an isocyanate group with hydroxyethyl (meth) acrylate.
  • the polymer chain contained in the structural unit represented by the general formula (IV) includes methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, among the structural units described above.
  • Those having a structural unit derived from (meth) acrylate, dicyclopentanyl (meth) acrylate, adamantyl (meth) acrylate, styrene, ⁇ -methylstyrene, vinylcyclohexane and the like are preferable. However, it is not limited to these.
  • R 32 and R 36 those having excellent solubility with an organic solvent described later are preferably used, and are selected appropriately according to the organic solvent used in the colorant dispersion liquid. It should be done. Specifically, for example, when the organic solvent is an organic solvent such as an ether alcohol acetate type, an ether type, an ester type or the like generally used as an organic solvent for a colorant dispersion, a methyl group, an ethyl group, Group, isobutyl group, n-butyl group, 2-ethylhexyl group, 2-ethoxyethyl group, cyclohexyl group, benzyl group and the like are preferable.
  • the organic solvent is an organic solvent such as an ether alcohol acetate type, an ether type, an ester type or the like generally used as an organic solvent for a colorant dispersion
  • the reason for setting the R 32 and R 36 in this way is that the structural unit containing the R 32 and R 36 is soluble in the organic solvent, and the acidic phosphorus compound group of the monomer and This is because the dispersibility and stability of the particles such as the color material can be made particularly excellent because the salt portion has high adsorptivity to the particles such as the color material.
  • the Polymer may further have other structural units as long as the effects of the present disclosure are not impaired.
  • the structural unit represented with the following general formula (V) is mentioned suitably from the point of the dispersibility and dispersion stability of a coloring material.
  • m is an integer of 1 or more and 5 or less, preferably an integer of 2 or more and 5 or less, more preferably an integer of 4 or 5.
  • the number of units n and n ′ of the constituent units of the polymer chain may be an integer of 5 or more and 200 or less, and is not particularly limited, but is preferably in the range of 10 or more and 100 or less.
  • the ratio of the number of structural units represented by the general formula (V) is represented by the general formula (IV). It is preferably 0 or more and 30 mol% or less, and more preferably 10 mol% or more and 20 mol% or less with respect to the total number of structural units of the structural unit and the structural unit represented by the general formula (V).
  • the constitutional unit represented by the general formula (V) of Polymer is not more than the above upper limit value, it is more excellent in solvent resistance (particularly, N-methylpyrrolidone resistance; hereinafter referred to as NMP resistance). A coating film can be obtained.
  • the mass average molecular weight Mw of the polymer chain in Polymer is preferably in the range of 500 to 15000, more preferably in the range of 1000 to 8000.
  • the polymer chain in Polymer preferably has a solubility at 23 ° C. of 50 (g / 100 g solvent) or more with respect to the organic solvent used in combination.
  • the solubility of the polymer chain can be based on the fact that the raw material into which the polymer chain is introduced when preparing the graft copolymer has the solubility. For example, when a polymerizable oligomer containing a polymer chain and a group having an ethylenically unsaturated double bond at its end is used to introduce a polymer chain into the graft copolymer, the polymerizable oligomer has the solubility. Just do it.
  • a polymer chain containing a reactive group capable of reacting with a reactive group contained in the copolymer is used.
  • the polymer chain containing the reactive group may have the solubility.
  • the polymer chain may be a homopolymer or a copolymer. Moreover, the polymer chain contained in the structural unit represented by the general formula (II) may be used alone or in combination of two or more in the graft copolymer.
  • the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) are in a proportion of 3% by mass to 80% by mass in total. It is preferably contained, more preferably 10% by mass to 50% by mass, and still more preferably 20% by mass to 40% by mass.
  • the particles in the graft copolymer Since the ratio of the affinity part is appropriate and the decrease in solubility in an organic solvent can be suppressed, the adsorptivity to particles such as a coloring material is improved, and excellent dispersibility and dispersion stability are obtained. Further, since the acidic phosphorus compound group of the graft copolymer can be stably localized around the colorant, a color filter excellent in heat resistance and contrast can be obtained.
  • the structural unit represented by the general formula (II) is preferably contained in a proportion of 20% by mass to 97% by mass, and 50% by mass to 95% by mass. Is more preferable, and 60 mass% or more and 90 mass% or less are still more preferable.
  • the content ratio of the structural unit is represented by at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), and the general formula (II). It is calculated from the charged amount when synthesizing the graft copolymer having the structural unit.
  • the mass average molecular weight Mw of the graft copolymer is preferably in the range of 1000 or more and 100,000 or less, more preferably in the range of 3000 or more and 30000 or less, and in the range of 5000 or more and 20000 or less. More preferably. By being in the above range, particles such as a coloring material can be uniformly dispersed.
  • the mass average molecular weight Mw is a value measured by GPC (gel permeation chromatography).
  • HLC-8220GPC manufactured by Tosoh was used, the elution solvent was N-methylpyrrolidone to which 0.01 mol / liter of lithium bromide was added, and the polystyrene standard for calibration curve was Mw: 8 ⁇ 10 5 (F-80 ), Mw: 4 ⁇ 10 5 (F-40), Mw: 2 ⁇ 10 5 (F-20), Mw: 1 ⁇ 10 5 (F-10), Mw: 4 ⁇ 10 4 (F-4), Mw: 2 ⁇ 10 4 (F-2), Mw: 5 ⁇ 10 3 (A-5000), Mw: 2.5 ⁇ 10 3 (A-2500), Mw: 1 ⁇ 10 3 (A-1000), Mw: 5 ⁇ 10 2 (A-500) (above, manufactured by Tosoh Corporation), and TSK-GEL ALPHA-M ⁇ 2 (manufactured by Tosoh Corporation) as the measurement column.
  • the graft copolymer used in the embodiment of the present disclosure is represented by the structural unit represented by the general formula (I), the structural unit represented by the general formula (I ′), and the general formula (II). Other structural units may be included in addition to the structural units. It is copolymerizable with an ethylenically unsaturated double bond-containing monomer or the like that derives at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′). An ethylenically unsaturated double bond-containing monomer can be appropriately selected and copolymerized to introduce other structural units.
  • the method for producing the graft copolymer includes at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′). Any method can be used as long as it can produce a graft copolymer having the structural unit represented by the general formula (II), and is not particularly limited.
  • a graft copolymer having the structural unit represented by the general formula (I) and the structural unit represented by the general formula (II) for example, a monomer represented by the general formula (Ia) And a polymerizable oligomer comprising a polymer chain having at least one structural unit represented by the general formula (IV) or the general formula (V) and a group having an ethylenically unsaturated double bond at its terminal.
  • a reactive group such as an epoxy group or a cyclic ether group
  • an acidic phosphorus compound (R 2 P ( ⁇ O) (OH) 2 ) having a desired structure is added to the structural unit derived from the monomer having a reactive group, thereby adding the general formula ( I)
  • Examples thereof include a method of forming a structural unit.
  • the graft copolymer which has a structural unit represented by the said general formula (I '), and a structural unit represented by the said general formula (II), it represents with the said general formula (I).
  • a salt forming agent including an organic cation is further added, and the mixture is heated and stirred as necessary.
  • a salt between the acidic phosphorus compound group of the structural unit represented by the general formula (I) and the organic cation is obtained to obtain the structural unit represented by the general formula (I ′) Is mentioned. What is necessary is just to select suitably as said salt formation agent according to the organic cation to introduce
  • the salt forming agent when introducing a protonated nitrogen-containing organic cation as an organic cation, various corresponding tertiary amine compounds and imidazole compounds can be used.
  • the addition amount of the salt forming agent only needs to exhibit good dispersibility and dispersion stability, and may be appropriately adjusted according to the proportion of the structural unit to be introduced.
  • the salt forming agent is generally represented by the general formula (I). It is about 0.05 mol equivalent or more and 1.00 mol equivalent or less, preferably 0.3 mol equivalent or more and 0.5 mol equivalent or less with respect to the phosphorus site contained in the structural unit. If necessary, other monomers can also be used to produce a graft copolymer using a known polymerization means.
  • a polymer chain may be introduced using a polymer chain.
  • a functional group that reacts with the substituent is added.
  • the polymer chain may be introduced by reacting with the polymer chain contained therein.
  • a copolymer having a glycidyl group at the side chain is reacted with a polymer chain having a carboxyl group at the terminal, or a copolymer having an isocyanate group at the side chain is reacted with a polymer chain having a hydroxy group at the terminal.
  • polymer chains can be introduced.
  • additives generally used in the polymerization for example, a polymerization initiator, a dispersion stabilizer, a chain transfer agent and the like may be used.
  • an acidic phosphorus compound having a desired structure is converted into an ethylenically unsaturated diglycol group, an alicyclic epoxy group, an oxetane group, a hydroxyl group, or the like.
  • the method of making it react with the compound which has a heavy bond is mentioned.
  • a preferred block copolymer as a dispersant is one or more selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), and And a structural unit represented by the general formula (III).
  • the block copolymer will be described. However, since the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) are as described above, the description here is as follows. Omitted.
  • the structural unit represented by the general formula (I) and the general formula (I ′) is preferably 3 or more.
  • the structural unit represented by the general formula (I) and the general formula (I ′) is only required to function as a colorant affinity site, and is composed of one type. Alternatively, two or more structural units may be included.
  • the block part containing at least one kind selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) has two or more kinds in the block portion.
  • the structural units may be arranged at random.
  • the total content of the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) is 100 masses of all the structural units of the block copolymer.
  • % Is preferably 5% by mass or more and 60% by mass or less, more preferably 10% by mass or more and 50% by mass or less, and further preferably 20% by mass or more and 40% by mass or less. If it is within the above range, the ratio of the affinity site with the particles in the block copolymer becomes appropriate, and the decrease in solubility in organic solvents can be suppressed, so that the adsorptivity to particles such as coloring materials becomes good, Excellent dispersibility and dispersion stability can be obtained.
  • the acidic phosphorus compound group of the block copolymer can be stably localized around the colorant, a color filter having excellent heat resistance and contrast can be obtained.
  • the content rate of the said structural unit is computed from the preparation amount at the time of synthesize
  • the block copolymer has a block part containing the structural unit represented by the general formula (III), thereby improving the solvent affinity, the dispersibility and dispersion stability of the coloring material, and the heat resistance. In addition, the NMP resistance is excellent.
  • R 23 represents a hydrocarbon group, — [CH (R 24 ) —CH (R 25 ) —O] x2 —R 26 , — [(CH 2 ) y2 —O] z2 —R 26. , — [CO— (CH 2 ) y2 —O] z2 —R 26 , —CO—O—R 26 ′ or —O—CO—R 26 ′′ .
  • the hydrocarbon group for R 23 can be the same as that shown for R 2 above.
  • R 26 represents a hydrogen atom, a hydrocarbon group, a monovalent group represented by —CHO, —CH 2 CHO, or —CH 2 COOR 27
  • R 12 ′ represents a hydrocarbon group, — [CH ( R 24 ) —CH (R 25 ) —O] x2 ′ —R 26 , — [(CH 2 ) y2 ′ —O] z2 ′ —R 26 , — [CO— (CH 2 ) y2 ′ —O] z2 ′ —R 26 is a monovalent group
  • R 26 ′′ is an alkyl group having 1 to 18 carbon atoms
  • R 27 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • hydrocarbon group may have a substituent.
  • the hydrocarbon group for R 26 may be the same as that shown for R 2 .
  • x2 and x2 ′ are the same as x
  • y2 and y2 ′ are the same as y
  • z2 and z2 ′ are the same as z.
  • R 23 in the structural unit represented by the general formula (III) may be the same or different.
  • R 23 and R 26 ′ those having excellent solubility with a solvent described later are preferably used, and examples thereof include those similar to R 32 and R 36 .
  • R 23 , R 26 , R 26 ′ , R 26 ′′ and R 27 are within a range that does not hinder the dispersion performance of the block copolymer, etc., and are alkoxy groups, hydroxyl groups, carboxyl groups, amino groups, epoxy groups. It may be substituted with a substituent such as an isocyanate group or a hydrogen bond-forming group, and after the synthesis of the block copolymer, it is reacted with a compound having the substituent to add the substituent. Also good.
  • a compound having a functional group that reacts with the substituent and a polymerizable group may be reacted to add a polymerizable group.
  • adding a polymerizable group by reacting a block copolymer having a glycidyl group with (meth) acrylic acid or reacting a block copolymer having an isocyanate group with hydroxyethyl (meth) acrylate. Can do.
  • the number of structural units constituting the block part including the structural unit represented by the general formula (III) is not particularly limited, but the solvent affinity part and the colorant affinity part effectively act, and the colorant dispersion liquid From the viewpoint of improving dispersibility, it is preferably 10 or more and 200 or less, more preferably 20 or more and 100 or less, and still more preferably 30 or more and 80 or less.
  • the content of the structural unit represented by the general formula (III) is 40% by mass or more and 95% by mass or less when the total structural unit of the block copolymer is 100% by mass. It is preferable that it is 60 mass% or more and 90 mass% or less.
  • the content rate of the said structural unit is computed from the preparation amount at the time of synthesize
  • the block part including the structural unit represented by the general formula (III) may be selected so as to function as a solvent affinity site, and the structural unit represented by the general formula (III) is composed of one kind. There may be two or more structural units. In the embodiment of the present disclosure, when the structural unit represented by the general formula (III) includes two or more structural units, the block portion including the structural unit represented by the general formula (III) includes two types. The above structural units may be arranged at random.
  • the ratio m / n of the number of units n of the structural units of the block part including the structural unit represented by the general formula (III) is preferably in the range of 0.01 or more and 1 or less. A range of 1 or more and 0.7 or less is more preferable from the viewpoint of dispersibility and dispersion stability of the color material.
  • a block part containing at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′) and the general formula ( III) is not particularly limited as long as it can stably disperse the colorant, and the structural unit represented by the general formula (I) and The block part containing at least one selected from the structural unit represented by the general formula (I ′) is bonded to only one end of the block copolymer, and is excellent in interaction with the colorant and dispersed. It is preferable from the point which can suppress effectively aggregation of agents.
  • the mass average molecular weight of the block copolymer is not particularly limited, it is preferably 2500 or more and 30000 or less, more preferably 3000 or more and 20000 or less from the viewpoint of good dispersibility and excellent heat resistance. More preferably, it is 6000 or more and 15000 or less.
  • Method for producing block copolymer As the method for producing the block copolymer, a block part containing at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), and the general The method is not particularly limited as long as it is a method capable of producing a block copolymer having a block part including a structural unit represented by the formula (III).
  • a monomer having a reactive group such as a cyclic epoxy group, an oxetane group, or a hydroxyl group and an ethylenically unsaturated double bond
  • a monomer for deriving the structural unit represented by the general formula (III) can be used for living polymerization After copolymerizing by a known polymerization method to synthesize a block copolymer, an acidic phosphorus compound having a desired structure (R 2 P ( ⁇ O) (OH) 2 ) is derived from the monomer having the reactive group.
  • Composition unit A method of forming the structural unit represented by the general formula (I) by adding to the above can be mentioned.
  • the block copolymer which has a structural unit represented by the said general formula (I '), and a structural unit represented by the said general formula (III) it represents with the said general formula (I).
  • a salt forming agent including an organic cation is further added, and the mixture is heated and stirred as necessary.
  • the same salt forming agent as that used in the production of the graft copolymer can be used, and the content ratio of the salt forming agent is the same as that in the production of the graft copolymer. be able to.
  • the content ratio of the (B) dispersant may be adjusted as appropriate, but from the viewpoint of dispersibility and storage stability, (A) 5 parts by mass or more and 80 parts by mass with respect to 100 parts by mass of the color material. It is preferable to set it as follows, and it is more preferable to set it as 20 to 60 mass parts.
  • the colorant dispersion according to an embodiment of the present disclosure is a solvent having an SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less as the solvent (C).
  • a mixed solvent of (1) and a solvent (2) having an SP value of 7.8 (cal / cm 3 ) 1/2 or more and less than 8.6 (cal / cm 3 ) 1/2 is used.
  • the SP value (solubility parameter) of the solvent is a value calculated based on the definition of Hildebrand represented by the following formula (1), and the SP value tends to increase as the polarity increases.
  • Solubility parameter ( ⁇ ) ( ⁇ E v / V) 1/2 (In the formula (1), ⁇ E v represents the cohesive energy of the solvent, and V represents the molar volume of the solvent.)
  • the solvent having a known SP value can be used with reference to literature values such as “" Polymer Handbook (Third Edition) ", J. BRANDRUP et al. (John Wiley & Sons).
  • the solvent does not react with each component in the color material dispersion and the color resin composition for color filter described later, and the above-mentioned SP can be used from among solvents that can dissolve or disperse each component. What satisfies the value (solubility parameter) may be appropriately selected.
  • Examples of the solvent having an SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less include propylene glycol monomethyl ether acetate (8.7), xylene (8 .8), toluene (8.8), ethyl acetate (9.0), benzene (9.2), cyclohexanol acetate (9.2), diethylene glycol ethyl methyl ether (9.3), methyl acetate (8.
  • Examples of the solvent having an SP value of 7.8 (cal / cm 3 ) 1/2 or more and less than 8.6 (cal / cm 3 ) 1/2 include, for example, diisobutyl ketone (7.8), isoamyl acetate (7 .8), 1,2-diethoxyethane (8.5), butyl acetate (8.5), amyl acetate (8.5), dipropylene glycol dimethyl ether (7.9), methyl isobutyl ketone (8.4) ), Isobutyl acetate (8.3), isopropyl acetate (8.5), n-pentyl propionate (8.4), ethylene glycol diethyl ether (8.3), dipropylene glycol methyl-n-propyl ether (8.
  • the solvent (1) is an SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less.
  • the solvent (2) is one kind of solvents having an SP value of 7.8 (cal / cm 3 ) 1/2 or more and less than 8.6 (cal / cm 3 ) 1/2. It can use individually or in combination of 2 or more types.
  • the mixing ratio of the solvent (1) and the solvent (2) is not particularly limited.
  • the mixing ratio of the solvent (1) and the solvent (2) is Solvent (1): solvent (2) is preferably 95: 5 to 40:60, more preferably 90:10 to 50:50 in terms of mass ratio.
  • the total content of the solvent (1) and the solvent (2) is preferably 95% by mass or more based on the total amount of the solvent. It is more preferably at least 9% by mass, and even more preferably at least 99.9% by mass.
  • the solvent (C) has a SP value of 9.4 (cal / cm 3 ) 1/2 or more and a SP value of 7 as long as the effects of the embodiment of the present disclosure are not impaired. .8 (cal / cm 3 )
  • the solvent may be less than 1/2 .
  • the solvent having an SP value of more than 9.4 (cal / cm 3 ) 1/2 is preferably 5% by mass or less based on the total amount of the solvent, and 1% by mass. More preferably, it is more preferably 0.1% by mass or less.
  • the solvent having an SP value of less than 7.8 (cal / cm 3 ) 1/2 is preferably 5% by mass or less, and preferably 1% by mass or less, based on the total amount of the solvent. It is more preferable that it is 0.1 mass% or less.
  • the solvent (C) is usually 50% by mass or more and 95% by mass or less, preferably 60% by mass or more and 85% by mass or less, with respect to the total amount of the color material dispersion. Prepared at a ratio of When there is too little solvent, a viscosity will rise and a dispersibility will fall easily. Moreover, when there are too many solvents, a coloring material density
  • the color material (A) can be appropriately selected and used from those capable of obtaining a desired color tone, and examples thereof include known dyes, organic pigments, and inorganic pigments.
  • a dye when used as a color material, it is used as a rake color material insolubilized in a solvent.
  • organic pigments examples include insoluble azo pigments, soluble azo pigments, phthalocyanine organic pigments, quinacridone organic pigments, perylene organic pigments, dioxazine organic pigments, nickel azo pigments, isoindolinone organic pigments, and pyranthrone organic pigments.
  • Organic solid solution pigments such as thioindigo organic pigments, condensed azo organic pigments, benzimidazolone organic pigments, quinophthalone organic pigments, isoindoline organic pigments, quinacridone solid solution pigments, perylene solid solution pigments, and other pigments, Examples thereof include carbon black.
  • CI color index
  • the inorganic pigment examples include barium sulfate, iron oxide, zinc oxide, barium carbonate, barium sulfate, silica, clay, talc, titanium oxide, calcium carbonate, synthetic mica, alumina, zinc white, lead sulfate, yellow lead, Examples include zinc yellow, red bean (red iron oxide (III)), cadmium red, ultramarine blue, bitumen, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, and inorganic solid solution pigments.
  • the color material dispersion can improve the heat resistance of the colored layer
  • (A) a rake color material having relatively poor heat resistance can be suitably used as the color material.
  • the lake color material refers to a color material in which a solvent-soluble color material is insolubilized by forming a salt with a counter ion.
  • the rake color material can be usually obtained by mixing a dye described later and a rake agent described later in a solvent.
  • the dye may be appropriately selected according to the desired color tone, and may be any basic skeleton (color development site) such as an azo dye, anthraquinone dye, triarylmethane dye, xanthene dye, cyanine dye, or indigo dye. ) May be used.
  • the dye may be a dye classified into any of an acidic dye having an anionic substituent and a basic dye having a cationic substituent.
  • the color material (A) is one or more selected from the group consisting of a triarylmethane color material and a xanthene color material from the viewpoint of color developability, light transmittance, heat resistance, and the like. It is preferable to use the coloring material.
  • acid dyes include C.I. I. Acid Violet 15, 16, 17, 19, 21, 21, 24, 25, 38, 49, 72, C.I. I. Acid Blue 13, 5, 7, 9, 19, 22, 83, 90, 93, 100, 103, 104, 109, C.I. I. Acid Green 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 18, 22, 50, 50: 1, etc. triarylmethane acid dyes; I. Acid Red 50, 51, 52, 87, 92, 94, 289, 388, C.I. I. And xanthene acid dyes such as Acid Violet 9, 30, 102 and Sulforhodamine 101.
  • xanthene acid dyes C.I. I. Acid Red 50, C.I. I. Acid Red 52, C.I. I. Acid Red 289, C.I. I. Acid Violet 9, C.I. I. Acid Violet 30, C.I. I. A rhodamine acid dye such as Acid Blue 19 is preferred.
  • the basic dye is an ionic dye having a cation moiety as a chromophore.
  • Specific examples include those with the following color index (CI) names.
  • Phthalocyanine dyes such as Basic Blue 140; C. I. Auramine dyes such as basic yellow 2, 3, 37; C. I. Basic Yellow 5, 6, 7, 9, C.I. I. Acridine dyes such as Basic Orange 4, 5, 14, 15, 16, 17, 18, 19, 2; C. I. Basic Red 12, 13, 14, 15, 27, 28, 37, 52, 90, C.I. I. Basic Blue 62, 63, C.I. I. Basic yellow 11, 13, 21, 22, 28, 29, 49, 51, 52, 53, C.I. I. Methine dyes such as Basic Violet 7, 15, 16, 20, 21, 22 etc.
  • a dye having a cation of a coloring material represented by the general formula (VI) described later is also preferable. These dyes can be used alone or in combination of two or more.
  • the counter ion differs depending on the type of the dye, the counter ion of the acid dye is a cation, and the counter ion of the basic dye is an anion. Therefore, the rake agent is appropriately selected and used depending on the dye. That is, when the acid dye is insolubilized, a compound that generates a counter cation of the dye is used as a rake agent. When the basic dye is insolubilized, a counter anion of the dye is generated as a rake agent. A compound is used.
  • ammonium cations As counter cations of acid dyes, ammonium cations, calcium ions, barium ions, strontium ions, manganese ions, aluminum ions, cesium ions, lanthanum ions, neodymium ions, cerium ions and other metal cations, polyaluminum chloride and oxychloride Examples include inorganic polymers such as zirconium.
  • a rake agent that generates ammonium ions for example, primary amine compounds, secondary amine compounds, tertiary amine compounds, and the like are preferable. Among them, secondary amines are preferred because of their excellent heat resistance and light resistance. It is preferable to use an amine compound or a tertiary amine compound.
  • the counter anion of the basic dye may be an organic anion or an inorganic anion.
  • the organic anion include organic compounds having an anionic group as a substituent.
  • the anionic group include —SO 2 N — SO 2 CH 3 , —SO 2 N — COCH 3 , —SO 2 N — SO 2 CF 3 , —SO 2 N — COCF 3 , —CF 2 SO 2 N - SO 2 CH 3, -CF 2 SO 2 N - COCH 3, -CF 2 SO 2 N - SO 2 CF 3, -CF 2 SO 2 N - COCF 3 or imidate group such as, -SO 3 -, —CF 2 SO 3 ⁇ , —PO 3 2 ⁇ , —COO ⁇ , —CF 2 PO 3 2 ⁇ , —CF 2 COO — and the like can be mentioned.
  • an imido acid group, —SO 3 ⁇ , and —CF 2 SO 3 — are preferable, and —SO 3 — (a sulfonate group) is more preferable.
  • the inorganic anion for example, an anion of oxo acid (phosphate ion, sulfate ion, chromate ion, tungstate ion (WO 4 2 ⁇ ), molybdate ion (MoO 4 2 ⁇ ), etc.) Mention may be made of inorganic anions such as polyacid anions condensed with oxo acids and mixtures thereof.
  • the polyacid may be an isopolyacid anion (M m O n ) c- or a heteropoly acid anion (X l M m O n ) c- .
  • M represents a poly atom
  • X represents a hetero atom
  • m represents a composition ratio of poly atoms
  • n represents a composition ratio of oxygen atoms.
  • the poly atom M include Mo, W, V, Ti, and Nb.
  • the hetero atom X include Si, P, As, S, Fe, and Co.
  • a polyacid anion containing at least one of molybdenum (Mo) and tungsten (W) is preferable, and a c-valent polyacid anion containing at least tungsten is more preferable.
  • polyacid anions containing at least one of molybdenum and tungsten include isopolyacids such as tungstate ion [W 10 O 32 ] 4 ⁇ , molybdate ion [Mo 6 O 19 ] 2 ⁇ , and heteropolyacid.
  • isopolyacids such as tungstate ion [W 10 O 32 ] 4 ⁇ , molybdate ion [Mo 6 O 19 ] 2 ⁇ , and heteropolyacid.
  • ion phosphotungstic acid [PW 12 O 40] 3- silicotungstic acid ion [SiW 12 O 40] 4-, phosphomolybdic acid ion [PMo 12 O 40] 3-, phosphorus tongue strike molybdate [PW 12- x Mo x O 40 ] 3 ⁇
  • the polyacid anion containing at least one of molybdenum and tungsten is preferably a heteropolyacid among the above from the viewpoint of heat resistance and the availability of raw materials, and further a heteropolyacid containing phosphorus (P). It is more preferable that
  • rake agents that generate inorganic anions include alkali salts and alkali metal salts of the above inorganic anions.
  • the counter anion of the basic dye in the lake color material can be used alone or in combination of two or more.
  • the lake color material is preferably a metal lake color material of a basic dye from the viewpoint of heat resistance and light resistance.
  • the at least one metal lake colorant is preferably used.
  • the rake colorant is excellent in heat resistance and light resistance, and achieves high brightness of the color filter, so that at least one of triarylmethane basic dye and xanthene basic dye is used.
  • the color material (A-1) represented by the following general formula (VI) is preferably included.
  • A is an a-valent organic group in which the carbon atom directly bonded to N has no ⁇ bond, and the organic group is saturated aliphatic carbonized at least at the terminal directly bonded to N.
  • B c- represents a polyvalent polyvalent R i , R ii , R iii , R iv , and R v each independently represent a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group R ii and R iii , R iv and R v may combine to form a ring structure
  • Ar 1 represents a divalent aromatic group which may have a substituent.
  • R i to R v and Ar 1 may be the same or different.
  • a and c represent an integer of 2 or more
  • b and d represent an integer of 1 or more.
  • e is 0 or 1, and when e is 0, there is no bond.
  • a plurality of e may be the same or different.
  • the color material represented by the general formula (VI) includes a divalent or higher valent anion and a divalent or higher cation, in the aggregate of the color material, the anion and the cation are simply one molecule to one molecule. It is presumed that they form a molecular aggregate in which a plurality of molecules are associated via ionic bonds, rather than ionic bonds. Therefore, the apparent molecular weight of the color material represented by the general formula (VI) is remarkably increased as compared with the molecular weight of the conventional lake color material. It is presumed that the formation of such molecular aggregates increases the cohesive force in the solid state, lowers the thermal motion, suppresses dissociation of ion pairs and decomposition of the cation part, and improves heat resistance.
  • a in the general formula (VI) is an a-valent organic group in which the carbon atom directly bonded to N (nitrogen atom) does not have a ⁇ bond, and the organic group is saturated at least at the terminal directly bonded to N.
  • an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at the terminal directly bonded to N is linear, branched or cyclic unless the terminal carbon atom directly bonded to N has a ⁇ bond.
  • the carbon atom other than the terminal may have an unsaturated bond, may have a substituent, and the carbon chain contains O, S, and N. Also good.
  • a carbonyl group, a carboxyl group, an oxycarbonyl group, an amide group or the like may be contained, and a hydrogen atom may be further substituted with a halogen atom or the like.
  • the aromatic group having an aliphatic hydrocarbon group in A is a monocyclic or polycyclic aromatic group having an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at the terminal directly bonded to N. And may have a substituent, and may be a heterocyclic ring containing O, S, and N. Especially, it is preferable that A contains a cyclic
  • the cyclic aliphatic hydrocarbon groups a bridged alicyclic hydrocarbon group is preferable from the viewpoint of skeleton fastness.
  • the bridged alicyclic hydrocarbon group means a polycyclic aliphatic hydrocarbon group having a bridged structure in the aliphatic ring and having a polycyclic structure, for example, norbornane, bicyclo [2,2,2]. Examples include octane and adamantane.
  • norbornane is preferable.
  • the group containing a benzene ring and a naphthalene ring is mentioned, for example, Among these, the group containing a benzene ring is preferable.
  • A when A is a divalent organic group, it has 1 to 20 carbon atoms such as a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or a xylylene group.
  • An aromatic group in which two alkylene groups are substituted is exemplified.
  • the valence a is the number of chromogenic cation sites constituting the cation, and a is an integer of 2 or more.
  • the heat resistance is excellent.
  • the upper limit of a is not particularly limited, but a is preferably 4 or less, and more preferably 3 or less, from the viewpoint of ease of production.
  • the alkyl group for R i to R v is not particularly limited.
  • a linear or branched alkyl group having 1 to 20 carbon atoms can be mentioned, among which a linear or branched alkyl group having 1 to 8 carbon atoms is preferable.
  • a linear or branched alkyl group having 1 to 5 carbon atoms is more preferable from the viewpoints of luminance and heat resistance.
  • the alkyl group in R i to R v is particularly preferably an ethyl group or a methyl group.
  • the substituent that the alkyl group may have is not particularly limited, and examples thereof include an aryl group, a halogen atom, and a hydroxyl group, and examples of the substituted alkyl group include a benzyl group.
  • the aryl group in R i to R v is not particularly limited. For example, a phenyl group, a naphthyl group, etc. are mentioned. Examples of the substituent that the aryl group may have include an alkyl group and a halogen atom.
  • R ii and R iii , R iv and R v are combined to form a ring structure.
  • R ii and R iii , R iv and R v form a ring structure through a nitrogen atom Say.
  • the ring structure is not particularly limited, and examples thereof include a pyrrolidine ring, a piperidine ring, and a morpholine ring.
  • R i to R v are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group, or R ii and R iii , R iv. And R v are preferably bonded to form a pyrrolidine ring, piperidine ring, or morpholine ring.
  • R i to R v can each independently have the above-described structure, and among these, R i is preferably a hydrogen atom from the viewpoint of color purity, and R ii to R ii from the viewpoint of ease of production and raw material procurement. More preferably, R v are all the same.
  • the divalent aromatic group in Ar 1 is not particularly limited.
  • the aromatic group for Ar 1 the same aromatic groups as those described for the aromatic group for A can be used.
  • Ar 1 is preferably an aromatic group having 6 to 20 carbon atoms, and more preferably an aromatic group composed of a condensed polycyclic carbocycle having 10 to 14 carbon atoms. Among these, a phenylene group or a naphthylene group is more preferable because the structure is simple and the raw material is inexpensive.
  • a plurality of R i to R v and Ar 1 in one molecule may be the same or different.
  • the color development site exhibits the same color development, so that the same color as the single color development site can be reproduced, which is preferable from the viewpoint of color purity.
  • at least one of R i to R v and Ar 1 is a different substituent, a color obtained by mixing a plurality of types of monomers can be reproduced and adjusted to a desired color. it can.
  • the anion portion (B c ⁇ ) is a polyacid anion having a valence of 2 or more.
  • the polyacid anion may be an isopolyacid ion (M m O n ) d- or a heteropoly acid ion (X 1 M m O n ) d- .
  • M represents a poly atom
  • X represents a hetero atom
  • m represents a composition ratio of poly atoms
  • n represents a composition ratio of oxygen atoms.
  • the poly atom M include Mo, W, V, Ti, and Nb.
  • the hetero atom X include Si, P, As, S, Fe, and Co.
  • a counter cation such as Na + or H + may be partially included.
  • a polyacid anion containing at least one of tungsten (W) and molybdenum (Mo), including at least tungsten and containing molybdenum. It is more preferable that it is a good polyacid anion from the viewpoint of heat resistance.
  • Examples of the polyacid anion containing at least one of tungsten (W) and molybdenum (Mo) include, for example, isopolyacid, tungstate ion [W 10 O 32 ] 4 ⁇ , molybdate ion [Mo 6 O 19 ] 2.
  • the polyacid anion containing at least one of tungsten (W) and molybdenum (Mo) is preferably a heteropolyacid among the above from the viewpoint of heat resistance and the availability of raw materials, and more preferably P ( More preferred is a heteropolyacid containing phosphorus.
  • the polyacid anion in the colorant represented by the general formula (VI) can be used alone or in combination of two or more of the above anions.
  • the overall ratio of tungsten to molybdenum is preferably 90:10 to 100: 0 from the viewpoint of heat resistance and light resistance.
  • b represents the number of cations
  • d represents the number of anions in the molecular aggregate
  • b and d represent an integer of 1 or more.
  • a plurality of cations in the molecular aggregate may be one kind alone, or two or more kinds may be combined.
  • the anion present in the molecular aggregate may be a single anion or a combination of two or more, and an organic anion and an inorganic anion may be used in combination. .
  • E in the general formula (VI) is an integer of 0 or 1.
  • a plurality of e may be the same or different. That is, for example, it may be a cation moiety having only a triarylmethane skeleton or a plurality of xanthene skeletons, or may be a cation moiety containing both a triarylmethane skeleton and a xanthene skeleton in one molecule. From the viewpoint of color purity, a cation moiety having only the same skeleton is preferable.
  • the color material represented by the general formula (VI) can be adjusted to a desired color.
  • the average dispersed particle diameter of the color material is not particularly limited as long as the desired color development is possible, and varies depending on the type of the color material to be used. From the viewpoint of obtaining coloring power, it is preferably in the range of 5 nm to 300 nm, more preferably in the range of 30 nm to 200 nm.
  • the content of the coloring material is not particularly limited as long as a desired colored layer can be formed, and is appropriately adjusted. Specifically, although it varies depending on the type of pigment, it is preferably in the range of 0.05% by mass or more and 20% by mass or less, and preferably 1% by mass or more and 15% by mass or less with respect to the total amount of the colorant dispersion. More preferably within the range.
  • dispersion auxiliary resin examples include alkali-soluble resins exemplified by a colored resin composition for a color filter described later.
  • the steric hindrance of the alkali-soluble resin makes it difficult for the colorant particles to come into contact with each other, and may have the effect of stabilizing the dispersion or reducing the dispersant due to the dispersion stabilizing effect.
  • Other components include, for example, surfactants for improving wettability, silane coupling agents for improving adhesion, antifoaming agents, repellency inhibitors, antioxidants, anti-aggregation agents, and UV absorbers. Etc.
  • the colorant dispersion according to the embodiment of the present disclosure is suitably used as a preliminary preparation for preparing a colored resin composition for a color filter described later. That is, the color material dispersion is preliminarily prepared in the pre-stage of preparing a colored resin composition described later, (color material component mass in the composition) / (solid content mass other than the color material component in the composition) ) Colorant dispersion with a high ratio. Specifically, the ratio of (mass of color material component in composition) / (mass of solid content other than color material component in composition) is usually 1.0 or more.
  • solid content means all components other than the solvent.
  • a method for producing a color material dispersion includes (A) a color material, (B) a dispersant, (C) a solvent, and various additive components used as desired.
  • any method may be used as long as it can be uniformly dispersed in the solvent (C) by the dispersing agent (B), and can be uniformly dispersed by mixing using a known mixing means.
  • a dispersant is mixed with (C) a solvent and stirred to prepare a dispersant solution, and then the (A) colorant is added to the dispersant solution.
  • other components are mixed and dispersed using a known stirrer or disperser.
  • a coloring material (B) a dispersant, and a solvent having an SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less (1) And a solvent having an SP value of 7.8 (cal / cm 3 ) 1/2 or more and less than 8.6 (cal / cm 3 ) 1/2 after being dispersed using a known stirrer or disperser (2)
  • a colorant dispersion may be prepared by adjusting the mixing.
  • the dispersing machine for performing the dispersion treatment examples include a roll mill such as a two-roll or a three-roll, a ball mill such as a ball mill or a vibration ball mill, a bead mill such as a paint conditioner, a continuous disk type bead mill, or a continuous annular type bead mill.
  • the bead diameter to be used is preferably 0.03 mm or more and 2.00 mm or less, and more preferably 0.10 mm or more and 1.0 mm or less.
  • preliminary dispersion is performed with 2 mm zirconia beads having a relatively large bead diameter, and the main dispersion is further performed with 0.1 mm zirconia beads having a relatively small bead diameter.
  • the viscosity of the colorant dispersion according to an embodiment of the present disclosure is not particularly limited, but the shear viscosity at a shear rate of 60 rpm is 10 mPa ⁇ s or less from the viewpoint of good dispersibility and good handleability. It is preferable that it is 7 mPa ⁇ s or less.
  • the shear viscosity can be measured using a known viscoelasticity measuring apparatus and is not particularly limited. For example, the shear viscosity can be measured using “Rheometer MCR301” manufactured by Anton Paar.
  • Colored resin composition for color filter includes the color material dispersion and (D) a binder component. That is, the colored resin composition for a color filter according to an embodiment of the present disclosure contains (A) a color material, (B) a dispersant, (C) a solvent, and (D) a binder component.
  • the dispersant is a polymer having at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), and (C)
  • the solvent has a SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less, and an SP value of 7.8 (cal / cm 3). ) 1/2 or more and 8.6 (cal / cm 3 )
  • the solvent (2) is contained in less than 1/2 .
  • the colored resin composition for a color filter according to an embodiment of the present disclosure is used in combination with the specific (B) dispersant and the specific (C) solvent, and thus has excellent dispersibility and storage stability, and has a long period of time. Even after storage, a colored layer having high contrast and excellent heat resistance can be formed.
  • the colored resin composition according to the embodiment of the present disclosure includes (A) a color material, (B) a dispersant, (C) a solvent, and (D) a binder component. As long as the effect is not impaired, other components may be contained as necessary.
  • a colored resin composition for a color filter will be described, but (A) the color material, (B) the dispersant, and (C) the solvent may be the same as the color material dispersion. Since it can do, description here is abbreviate
  • the colored resin composition for a color filter contains a binder component in order to impart film formability and adhesion to the surface to be coated. In order to impart sufficient hardness to the coating film, it is preferable to contain a curable binder component. It does not specifically limit as a curable binder component, The curable binder component used in forming the coloring layer of a conventionally well-known color filter can be used suitably. Examples of the curable binder component include a photocurable binder component containing a photocurable resin that can be polymerized and cured by visible light, ultraviolet light, electron beam, and the like, and a thermosetting resin that can be polymerized and cured by heating. What contains the thermosetting binder component to contain can be used.
  • the colored resin composition for a color filter can be selectively attached in a pattern on a substrate to form a colored layer, for example, when used in an inkjet method, developability is required for the curable binder component. Absent.
  • a well-known thermosetting binder component, a photosensitive binder component, etc. which are used when forming a color filter colored layer by an inkjet system etc. can be used suitably.
  • the thermosetting binder a combination of a compound having two or more thermosetting functional groups in one molecule and a curing agent is usually used, and a catalyst capable of promoting a thermosetting reaction may be added.
  • thermosetting functional group examples include an epoxy group, an oxetanyl group, an isocyanate group, and an ethylenically unsaturated bond.
  • An epoxy group is preferably used as the thermosetting functional group.
  • Specific examples of the thermosetting binder component include those described in International Publication No. 2012/144521 pamphlet.
  • the photosensitive binder component which has alkali developability is used suitably.
  • a curable binder component is not limited to these.
  • a thermosetting binder component that can be polymerized and cured by heating such as an epoxy resin may be further used.
  • Examples of the photosensitive binder component include a positive photosensitive binder component and a negative photosensitive binder component.
  • Examples of the positive photosensitive binder component include a system containing an alkali-soluble resin and an o-quinonediazide group-containing compound as a photosensitizing component.
  • the negative photosensitive binder component a system containing at least an alkali-soluble resin, a polyfunctional monomer, and a photoinitiator is preferably used.
  • a negative photosensitive binder component is preferable because a pattern can be easily formed by an existing process by a photolithography method.
  • the alkali-soluble resin, the polyfunctional monomer, and the photoinitiator constituting the negative photosensitive binder component will be specifically described.
  • the alkali-soluble resin in the present disclosure has an acidic group, acts as a binder resin, and is appropriately selected and used as long as it is soluble in a developer used for pattern formation, particularly preferably an alkali developer. be able to.
  • a preferable alkali-soluble resin in the present disclosure is preferably a resin having a carboxyl group as an acidic group, specifically, an acrylic copolymer having a carboxyl group, an epoxy (meth) acrylate resin having a carboxyl group, or the like. Can be mentioned.
  • acrylic copolymers and epoxy acrylate resins may be used as a mixture of two or more.
  • the acrylic copolymer having a carboxyl group is obtained by copolymerizing a carboxyl group-containing ethylenically unsaturated monomer and an ethylenically unsaturated monomer.
  • the acrylic copolymer having a carboxyl group may further contain a structural unit having an aromatic carbocyclic ring.
  • the aromatic carbocycle functions as a component that imparts coating properties to the colored resin composition for color filters.
  • the acrylic copolymer having a carboxyl group may further contain a structural unit having an ester group.
  • the structural unit having an ester group not only functions as a component that suppresses alkali solubility of the colored resin composition for a color filter, but also functions as a component that improves the solubility in a solvent and further the solvent resolubility.
  • acrylic copolymer having a carboxyl group examples include those described in International Publication No. 2012/144521 pamphlet. Specifically, for example, methyl (meth) acrylate, ethyl ( Examples thereof include a copolymer composed of a monomer having no carboxyl group, such as (meth) acrylate, and one or more selected from (meth) acrylic acid and anhydrides thereof.
  • a polymer having an ethylenically unsaturated bond introduced by adding an ethylenically unsaturated compound having a reactive functional group such as a glycidyl group or a hydroxyl group to the above copolymer can be exemplified, but the present invention is not limited thereto. Is not to be done.
  • a polymer having an ethylenically unsaturated bond introduced, for example, by adding an ethylenically unsaturated compound having a glycidyl group or a hydroxyl group to the copolymer is polymerized with a polyfunctional monomer described later at the time of exposure. This is particularly suitable in that the colored layer becomes more stable.
  • the copolymerization ratio of the carboxyl group-containing ethylenically unsaturated monomer in the carboxyl group-containing copolymer is usually 5% by mass or more and 50% by mass or less, preferably 10% by mass or more and 40% by mass or less.
  • the copolymerization ratio of the carboxyl group-containing ethylenically unsaturated monomer is less than 5% by mass, the solubility of the resulting coating film in an alkaline developer is lowered, and pattern formation becomes difficult.
  • the copolymerization ratio exceeds 50% by mass, there is a tendency that the formed pattern is easily detached from the substrate or the pattern surface is roughened during development with an alkali developer.
  • the preferred molecular weight of the carboxyl group-containing copolymer is preferably in the range of 1,000 to 500,000, and more preferably 3,000 to 200,000. If it is less than 1,000, the binder function after curing is remarkably lowered, and if it exceeds 500,000, pattern formation may be difficult during development with an alkaline developer.
  • Acrylate compounds are suitable.
  • the epoxy compound, unsaturated group-containing monocarboxylic acid, and acid anhydride can be appropriately selected from known ones. Specific examples include those described in International Publication No. 2012/144521 pamphlet. Each of the epoxy compound, the unsaturated group-containing monocarboxylic acid, and the acid anhydride may be used alone or in combination of two or more.
  • the alkali-soluble resin used in the colored resin composition for color filters may be used alone or in combination of two or more, and the content thereof is a color contained in the colored resin composition. It is usually in the range of 10 to 1000 parts by mass, preferably in the range of 20 to 500 parts by mass with respect to 100 parts by mass of the material. If the content of the alkali-soluble resin is too small, sufficient alkali developability may not be obtained, and if the content of the alkali-soluble resin is too large, the ratio of the coloring material is relatively low, which is sufficient. The coloring density may not be obtained.
  • the polyfunctional monomer used in the colored resin composition for a color filter is not particularly limited as long as it can be polymerized by a photoinitiator described later, and usually has two or more ethylenically unsaturated double bonds.
  • polyfunctional (meth) acrylates having two or more acryloyl groups or methacryloyl groups are preferable.
  • Such polyfunctional (meth) acrylate may be appropriately selected from conventionally known ones. Specific examples include those described in International Publication No. 2012/144521 pamphlet.
  • polyfunctional (meth) acrylates may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the polyfunctional monomer has three (trifunctional) or more polymerizable double bonds. It is preferable to use poly (meth) acrylates of polyhydric alcohols having a valence of 3 or more and their dicarboxylic acid modified products.
  • the content of the said polyfunctional monomer used in the colored resin composition for color filters Usually, about 5 mass parts or more and about 500 mass parts or less with respect to 100 mass parts of said alkali-soluble resin, Preferably it is 20.
  • the range is not less than 300 parts by mass. If the content of the polyfunctional monomer is less than the above range, the photocuring may not sufficiently proceed and the exposed part may be eluted, and if the content of the polyfunctional monomer is more than the above range, the alkali developability may be deteriorated. There is.
  • Photoinitiator There is no restriction
  • the content of the photoinitiator used in the colored resin composition for a color filter is usually about 0.01 parts by mass or more and 100 parts by mass or less, preferably 5 parts by mass or more and 60 parts by mass with respect to 100 parts by mass of the polyfunctional monomer. Or less.
  • this content is less than the above range, the polymerization reaction cannot be sufficiently caused, so that the hardness of the colored layer may not be sufficient.
  • the content of the coloring material or the like in the solid content is relatively small, and a sufficient coloring density cannot be obtained.
  • the colored resin composition for a color filter may contain other components as necessary within a range not impairing the effects of the present disclosure.
  • other components include an antioxidant, a polymerization terminator, a chain transfer agent, a leveling agent, a plasticizer, a surfactant, an antifoaming agent, a silane coupling agent, an ultraviolet absorber, and an adhesion promoter.
  • Specific examples of the surfactant and the plasticizer include those described in International Publication No. 2012/144521 pamphlet.
  • the colored resin composition for a color filter preferably further contains an antioxidant from the viewpoint of heat resistance and light resistance.
  • the antioxidant may be appropriately selected from conventionally known antioxidants. Specific examples of antioxidants include, for example, hindered phenol antioxidants, amine antioxidants, phosphorus antioxidants, sulfur antioxidants, hydrazine antioxidants, and the like. From the viewpoint, it is preferable to use a hindered phenol-based antioxidant.
  • the hindered phenol antioxidant contains at least one phenol structure, and has a structure in which a substituent having 4 or more carbon atoms is substituted on at least one of the 2-position and 6-position of the hydroxyl group of the phenol structure. Means an antioxidant.
  • hindered phenol antioxidant examples include, for example, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: Irganox 1010, manufactured by BASF).
  • 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate (trade name: Irganox 3114, manufactured by BASF), 2,4,6-tris (4-hydroxy- 3,5-di-tert-butylbenzyl) mesitylene (trade name: Irganox 1330, manufactured by BASF), 6- (4-hydroxy-3,5-di-tert-butylanilino) -2,4-bis (octylthio) -1,3,5-triazine (trade name: Irganox 565, manufactured by BASF), 2,2′-thiodiethylbi [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: Irganox 1035, manufactured by BASF), 1,2-bis [3- (4-hydroxy-3,5 -Di-tert-butylphenyl) propionyl] hydrazine (trade name:
  • the amount of the antioxidant is not particularly limited as long as the effect of the present disclosure is not impaired.
  • a compounding quantity of antioxidant it is preferable that antioxidant is 0.1 mass part or more and 5.0 mass part or less with respect to 100 mass parts of total solids in a colored resin composition, 0.5 More preferably, it is at least 4.0 parts by mass. If it is more than the said lower limit, it is excellent in heat resistance. On the other hand, if it is below the said upper limit, a colored resin composition can be used as a highly sensitive photosensitive resin composition.
  • solvent for the purpose of adding (D) the binder component or the above-mentioned other components as a solution, or for diluting the colored resin composition for a color filter, etc.
  • a solvent may be further added to the material dispersion.
  • the solvent added at the time of preparing the colored resin composition for a color filter can be appropriately selected and used as long as the effects of the present disclosure are not impaired.
  • the solvent (1) having an SP value of 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less. and, it is preferable that the SP value is at least one kind of 7.8 (cal / cm 3) 1/2 or more 8.6 (cal / cm 3) 1/2 than the solvent (2).
  • the mixing ratio of the solvent (1) and the solvent (2) is not particularly limited, but the solvent (1) is excellent in dispersibility and storage stability.
  • the total content of the solvent (1) and the solvent (2) is 95% by mass or more based on the total amount of the solvent.
  • it is 99 mass% or more, and it is still more preferable that it is 99.9 mass% or more.
  • a solvent having an SP value exceeding 9.4 (cal / cm 3 ) 1/2 is a solvent.
  • the total amount is preferably 5% by mass or less, more preferably 1% by mass or less, and still more preferably 0.1% by mass or less.
  • the solvent having an SP value of less than 7.8 (cal / cm 3 ) 1/2 is included in the total amount of the solvent from the viewpoint of dispersibility of the color material.
  • it is preferably 5% by mass or less, more preferably 1% by mass or less, and still more preferably 0.1% by mass or less.
  • solid content is all things other than the solvent mentioned above, and a liquid polyfunctional monomer etc. are also contained.
  • the content of the (B) dispersant is not particularly limited as long as it can uniformly disperse the color material (A).
  • the content of the solid content of the colored resin composition is not limited. On the other hand, 3 mass% or more and 40 mass% or less can be used. Furthermore, it is preferable to mix
  • the binder component is blended such that the total amount thereof is 10% by mass or more and 92% by mass or less, preferably 15% by mass or more and 87% by mass or less, based on the total solid content of the colored resin composition. preferable. If it is more than the said lower limit, the colored layer which has sufficient hardness and adhesiveness with a board
  • (C) solvent in the range which can form a colored layer accurately.
  • content of (C) solvent is preferably in the range of 55% by mass to 95% by mass with respect to the total amount of the colored resin composition containing the solvent, and in particular, in the range of 65% by mass to 88% by mass. Is more preferable.
  • the content of the solvent is within the above range, the coating property can be excellent.
  • the method for producing a colored resin composition for a color filter includes (A) a color material, (B) a dispersant, (C) a solvent, (D) a binder component, and various additive components used as desired.
  • the coloring material may be any method that can be uniformly dispersed in the solvent (C) from the dispersing agent (B), and is not particularly limited, and can be prepared by mixing using a known mixing means. it can.
  • the method (1) a method of mixing (D) the binder component and various additive components used as required in the color material dispersion; (2) (C) in a solvent, (A) Coloring material, (B) dispersing agent, (D) binder component, and various additive components used as desired are simultaneously added and mixed; (3) (C) (B) And (D) a binder, (D) a binder component, and various additive components used as desired, and after mixing, (A) a method of adding and mixing a coloring material; and the like.
  • the method (1) is preferable because it can effectively prevent aggregation of the color material and can be uniformly dispersed.
  • a color filter manufacturing method is a color filter manufacturing method including at least a transparent substrate and a colored layer provided on the transparent substrate, It has the process of forming at least 1 of a colored layer by hardening the colored resin composition for color filters which concerns on the said embodiment of this indication on a transparent substrate, It is characterized by the above-mentioned.
  • the color filter obtained by the above production method has high contrast and excellent heat resistance.
  • FIG. 1 is a schematic cross-sectional view illustrating an example of a color filter obtained by a method for manufacturing a color filter according to an embodiment of the present disclosure.
  • the color filter 10 obtained by the manufacturing method according to the embodiment of the present disclosure includes a transparent substrate 1, a light shielding part 2, and a colored layer 3.
  • At least one of the colored layers used in the color filter contains (A) a color material, (B) a dispersant, (C) a solvent, and (D) a binder component, and the (B) dispersant is: It is a polymer having at least one selected from the structural unit represented by the general formula (I) and the structural unit represented by the general formula (I ′), and the solvent (C) has an SP value. Is 8.6 (cal / cm 3 ) 1/2 or more and 9.4 (cal / cm 3 ) 1/2 or less, and the SP value is 7.8 (cal / cm 3 ) 1/2 or more.
  • the colored layer after hardening contains the said (A) color material and the said (B) dispersing agent at least.
  • the colored layer is usually formed in an opening of a light shielding part on a transparent substrate, which will be described later, and is usually composed of three or more colored patterns.
  • the arrangement of the colored layers is not particularly limited, and for example, a general arrangement such as a stripe type, a mosaic type, a triangle type, or a four-pixel arrangement type can be used.
  • variety, area, etc. of a colored layer can be set arbitrarily.
  • the thickness of the colored layer is appropriately controlled by adjusting the coating method, the solid content concentration, the viscosity, and the like of the colored resin composition for a color filter, but is usually preferably in the range of 1 ⁇ m to 5 ⁇ m.
  • the colored layer can be formed by the following method, for example.
  • a colored resin composition for a color filter is applied onto a transparent substrate described later using a coating means such as a spray coating method, a dip coating method, a bar coating method, a roll coating method, a spin coating method, a slit coating method, or a die coating method. Apply to form a wet coating.
  • a hot plate or oven After drying the wet coating film using a hot plate or oven, it is exposed to light through a mask having a predetermined pattern, and an alkali-soluble resin and a polyfunctional monomer are photopolymerized.
  • a photosensitive coating film is used.
  • Examples of the light source used for exposure include ultraviolet rays such as a low-pressure mercury lamp, a high-pressure mercury lamp, and a metal halide lamp, and an electron beam.
  • the exposure amount is appropriately adjusted depending on the light source used, the thickness of the coating film, and the like.
  • the heating conditions are appropriately selected depending on the blending ratio of each component in the colored resin composition to be used, the thickness of the coating film, and the like.
  • a coating film is formed with a desired pattern by melt
  • a solution in which an alkali is dissolved in water or a water-soluble solvent is usually used.
  • An appropriate amount of a surfactant or the like may be added to the alkaline solution.
  • a general method can be adopted as the developing method.
  • the developer is usually washed and the cured coating film of the colored resin composition is dried to form a colored layer.
  • the heating conditions are not particularly limited and are appropriately selected depending on the application of the coating film.
  • the light shielding part in the color filter is formed in a pattern on a transparent substrate described later, and can be the same as that used as a light shielding part in a general color filter.
  • the pattern shape of the light shielding portion is not particularly limited, and examples thereof include a stripe shape and a matrix shape.
  • Examples of the light-shielding portion include those obtained by dispersing or dissolving a black pigment in a binder resin, and metal thin films such as chromium and chromium oxide.
  • the metal thin film may be a CrO x film (x is an arbitrary number) and a laminate of two Cr films, and a CrO x film (x is an arbitrary number) with a reduced reflectance.
  • the light shielding part is a material in which a black color material is dispersed or dissolved in a binder resin
  • the light shielding part can be formed by any method that can pattern the light shielding part, and is not particularly limited. For example, a photolithography method, a printing method, an ink jet method and the like using the colored resin composition for the light shielding part can be exemplified.
  • the thickness of the light-shielding part is set to about 0.2 ⁇ m to 0.4 ⁇ m in the case of a metal thin film, and 0.5 ⁇ m to 2 ⁇ m in the case where a black color material is dispersed or dissolved in a binder resin. Set by degree.
  • the transparent substrate in the color filter is not particularly limited as long as it is a base material transparent to visible light, and a transparent substrate used for a general color filter can be used. Specifically, a transparent rigid material having no flexibility such as quartz glass, alkali-free glass, or synthetic quartz plate, or a flexible or flexible resin such as a transparent resin film, an optical resin plate, or flexible glass. A transparent flexible material is mentioned. Although the thickness of the said transparent substrate is not specifically limited, According to the use of a color filter, the thing about 100 micrometers or more and 1 mm or less can be used, for example.
  • the color filter of the present disclosure includes, for example, an overcoat layer, a transparent electrode layer, an alignment film for aligning a liquid crystal material, a columnar spacer, and the like in addition to the transparent substrate, the light shielding portion, and the colored layer. It may be.
  • the color filter of the present disclosure is not limited to the configuration exemplified above, and a known configuration generally used for a color filter can be appropriately selected and used.
  • Method of Manufacturing Liquid Crystal Display Device includes a step of manufacturing a color filter by the method of manufacturing a color filter according to the embodiment of the present disclosure, and the manufactured color filter. And a process of assembling the liquid crystal driving substrate to face each other.
  • the liquid crystal display device obtained by the manufacturing method according to the embodiment of the present disclosure includes the color filter obtained by the color filter manufacturing method according to the embodiment of the disclosure, the counter substrate, the color filter, and the counter substrate. And a liquid crystal layer formed between the two.
  • FIG. 2 is a schematic diagram illustrating an example of a liquid crystal display device obtained by the method of manufacturing a liquid crystal display device of the present disclosure.
  • the liquid crystal display device 40 of the present disclosure includes a color filter 10, a counter substrate 20 having a TFT array substrate and the like, and a liquid crystal layer formed between the color filter 10 and the counter substrate 20. 15.
  • the liquid crystal display device 40 of the present disclosure includes a color filter 10, a counter substrate 20 having a TFT array substrate and the like, and a liquid crystal layer formed between the color filter 10 and the counter substrate 20. 15.
  • the liquid crystal display device 40 includes a polarizing plate 25 a disposed outside the color filter 10, a polarizing plate 25 b disposed outside the counter substrate 20, and the counter substrate 20 of the liquid crystal display device 40.
  • positioned at the side is shown.
  • the liquid crystal display device of the present disclosure is not limited to the configuration illustrated in FIG. 2, and may be a configuration generally known as a liquid crystal display device using a color filter.
  • the driving method of the liquid crystal display device of the present disclosure is not particularly limited, and a driving method generally used for a liquid crystal display device can be employed. Examples of such a drive method include a TN method, an IPS method, an OCB method, and an MVA method. In the embodiment of the present disclosure, any of these methods can be suitably used. Further, the counter substrate can be appropriately selected and used according to the driving method of the liquid crystal display device of the present disclosure. Furthermore, as the liquid crystal constituting the liquid crystal layer, various liquid crystals having different dielectric anisotropy and mixtures thereof can be used depending on the driving method of the liquid crystal display device.
  • a method generally used as a method for manufacturing a liquid crystal cell can be used, and examples thereof include a vacuum injection method and a liquid crystal dropping method.
  • a vacuum injection method for example, a liquid crystal cell is prepared in advance using a color filter and a counter substrate, and the liquid crystal is heated to obtain an isotropic liquid, and the liquid crystal is applied to the liquid crystal cell using the capillary effect.
  • the liquid crystal layer can be formed by injecting in this state and sealing with an adhesive. Thereafter, the sealed liquid crystal can be aligned by slowly cooling the liquid crystal cell to room temperature.
  • liquid crystal dropping method for example, a sealant is applied to the periphery of the color filter, the color filter is heated to a temperature at which the liquid crystal becomes isotropic, and the liquid crystal is dropped in an isotropic liquid state using a dispenser or the like.
  • the liquid crystal layer can be formed by overlapping the color filter and the counter substrate under reduced pressure and bonding them with a sealant. Thereafter, the sealed liquid crystal can be aligned by slowly cooling the liquid crystal cell to room temperature.
  • the backlight can be appropriately selected and used depending on the use of the liquid crystal display device.
  • a cold cathode fluorescent tube CCFL: Cold Cathode Fluorescent Lamp
  • a backlight unit using a white LED or a white organic EL as a light source can be provided.
  • a white LED for example, a white LED that obtains white light by color mixing by combining a red LED, a green LED, and a blue LED, a white LED that obtains white light by color mixing by combining a blue LED, a red LED, and a green phosphor, and a blue LED White LED that obtains white light by mixing colors, white LED that obtains white light by mixing colors of blue LED and YAG phosphor, UV LED, red light emitting phosphor, and green light emitting fluorescence And a white LED that obtains white light by color mixing by combining a body and a blue light emitting phosphor.
  • the phosphor quantum dots may be used.
  • the color filter since the color filter includes a blue colored layer having high luminance, that is, high transmittance, compared with the backlight of the blue LED-YAG fluorescent system, the intensity of green and red is strong and the intensity of blue is relatively It is also preferably used for a weak backlight, for example, a combination of a white LED that obtains white light by mixing red, green, and blue.
  • a manufacturing method of an organic light emitting display device includes a step of manufacturing a color filter by the method of manufacturing a color filter according to the embodiment of the present disclosure, and a light emitting layer. A step of arranging the manufactured color filter on a surface of the substrate on the side having the light emitting layer is provided.
  • FIG. 3 is a schematic diagram illustrating an example of the organic light emitting display device obtained by the method of manufacturing the organic light emitting display device according to the embodiment of the present disclosure.
  • the organic light emitting display device 100 according to the present disclosure includes a color filter 10 and an organic light emitter 80.
  • An organic protective layer 50 and an inorganic oxide film 60 may be provided between the color filter 10 and the organic light emitter 80.
  • the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, and the cathode 76 are sequentially formed on the upper surface of the color filter. Examples thereof include a method and a method in which an organic light emitter 80 formed on another substrate is bonded onto the inorganic oxide film 60.
  • the transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, the cathode 76, and other configurations in the organic light emitting body 80 known structures can be appropriately used.
  • the organic light emitting display device 100 manufactured as described above can be applied to, for example, a passive drive type organic EL display or an active drive type organic EL display.
  • the organic light emitting display device is not limited to the configuration shown in FIG. 3, and may be a known configuration as an organic light emitting display device in which a color filter is generally used.
  • AIBN bisisobutyronitrile
  • the obtained macromonomer MM-1 was confirmed by GPC (gel permeation chromatography) under the conditions of N-methylpyrrolidone, 0.01 mol / L lithium bromide added / polystyrene standard, and the mass average molecular weight (Mw 4010, number average molecular weight (Mn) 1910, molecular weight distribution (Mw / Mn) was 2.10.
  • a mixed solution of 0 parts by mass and 0.5 parts by mass of AIBN was added dropwise over 1.5 hours, heated and stirred for 3 hours, and then a mixed solution of AIBN 0.10 parts by mass and PGMEA 10.0 parts by mass was added dropwise over 10 minutes. Further, by aging at the same temperature for 1 hour, a 25.0% by mass solution of graft copolymer A was obtained. As a result of GPC measurement, the obtained graft copolymer A had a mass average molecular weight (Mw) of 10570, a number average molecular weight (Mn) of 4370, and a molecular weight distribution (Mw / Mn) of 2.42.
  • Mw mass average molecular weight
  • Mn number average molecular weight
  • Mn molecular weight distribution
  • the progress of the esterification reaction of GMA of graft copolymer A and vinylphosphonic acid was confirmed by acid value measurement and 1 H-NMR measurement.
  • the acid value of the obtained phosphorus graft copolymer B was 106 mgKOH / g.
  • the progress of the esterification reaction of GMA and methyl phosphate of graft copolymer A was confirmed by acid value measurement and 1 H-NMR measurement.
  • the resulting phosphorus-based graft copolymer C had an acid value of 104 mgKOH / g.
  • the progress of the esterification reaction between GMA of graft copolymer A and paratoluenesulfonic acid was confirmed by acid value measurement and 1 H-NMR measurement.
  • the acid value of the obtained acidic graft copolymer X1 was 10 mgKOH / g.
  • a part by mass of the mixed solution was added dropwise over 60 minutes. The temperature was kept below 40 ° C. by cooling the reactor with an ice bath. After 1 hour, 50.0 parts by mass of glycidyl methacrylate was added dropwise over 30 minutes. After reacting for 1 hour, 1 part by mass of methanol was added to stop the reaction. 455.0 mass parts of PGMEA was added to the THF solution of the obtained block copolymer A, and solvent substitution was performed by evaporation to obtain a 25.0 mass% PGMEA solution of the block copolymer A.
  • the obtained block copolymer A had a mass average molecular weight (Mw) of 11320, a number average molecular weight (Mn) of 8950, and a molecular weight distribution (Mw / Mn) of 1.26.
  • Dispersor byk-111 (manufactured by Big Chemie Japan: ethylene glycol / polycaprolactone block copolymer phosphate ester, number average molecular weight 700, weight average molecular weight 2,200) as comparative dispersant X2, as comparative dispersant X3, Disper byk-161 (Bic Chemie Japan Co., Ltd .: urethane dispersant) was used as comparative dispersant X4, Disper byk-170 (Bic Chemie Japan Co., Ltd .: urethane dispersant) was used as comparative dispersant X5.
  • BYK-LPN21116 (manufactured by BYK Japan): quaternary ammonium salt-containing acrylate dispersant was used.
  • the obtained binder resin A had a mass average molecular weight (Mw) of 8850, a number average molecular weight (Mn) of 4200, a molecular weight distribution (Mw / Mn) of 2.11 and an acid value of 78 mgKOH / g.
  • the mixture was heated and stirred for 2 hours to obtain a binder resin B (solid content: 30% by mass).
  • the obtained binder resin B had a mass average molecular weight (Mw) of 4950, a number average molecular weight (Mn) of 2240, a molecular weight distribution (Mw / Mn) of 2.21, and an acid value of 64 mgKOH / g.
  • Binder composition B (Production Example 8 Preparation of binder composition B) PGMEA 11.33 parts by mass, binder resin B of Synthesis Example 7 (solid content 30% by mass) 26.67 parts by mass, Aronix M403 8.00 parts by mass, Irgacure 907 3.00 parts by mass, Kayacure DETX-S 1.00 parts by mass Binder composition B (solid content 40 mass%) was prepared by mixing parts.
  • Example 1 (1) Preparation of colorant dispersion 10.00 parts by mass of blue colorant A in Synthesis Example 1, 20.00 parts by mass of dispersant A solution in Production Example 1 (solid content of 5.00 parts by mass), Synthesis Example 6 Binder resin A 6.67 parts by weight (solid content 3.00 parts by weight), PGMEA (SP value 8.7 solvent) 51.03 parts by weight, diisobutyl ketone (DIBK: SP value 7.8 solvent) ) 12.30 parts by mass are mixed and dispersed in a paint shaker (manufactured by Asada Tekko Co., Ltd.) as a preliminary dispersion with 2 mm zirconia beads for 1 hour and further as a main dispersion with 0.1 mm zirconia beads for 6 hours. Obtained.
  • a paint shaker manufactured by Asada Tekko Co., Ltd.
  • Examples 2 to 14 (1) Preparation of Color Material Dispersion In Example 1, (1), except that the color material, the dispersant, and the solvent were changed to have the compositions shown in Table 1-1 below, ) To obtain colorant dispersions 2 to 14, respectively.
  • the blue colored resin compositions 2 to 14 of Examples 2 to 14 were obtained in the same manner as (2) of Example 1 except for the above changes.
  • Example 15 (1) Preparation of Color Material Dispersion Liquid 9.2 parts by mass of blue color material A of Synthesis Example 1, 0.8 part by mass of purple color material B of Synthesis Example 2, and 20.00 parts by mass of Dispersant A solution of Production Example 1 Parts (solid content: 5.00 parts by mass), 6.67 parts by mass of binder resin A of Synthesis Example 6 (solids: 3.00 parts by mass), PGMEA (solvent with SP value of 8.7) and 38.73 parts by mass , 24.60 parts by mass of diisobutyl ketone (DIBK: SP value 7.8 solvent) are mixed, and pre-dispersed with a paint shaker for 1 hour with 2 mm zirconia beads, and further with 0.1 mm zirconia beads for main dispersion for 6 hours.
  • DIBK diisobutyl ketone
  • Color material dispersion 15 obtained in (1) 43.64 parts by mass, binder composition A prepared in Production Example 7 25.11 parts by mass, PGMEA 30.70 parts by mass, Surfactant R08MH (manufactured by DIC) 0.05 part by mass and silane coupling agent KBM503 (manufactured by Shin-Etsu Silicone) 0.5 part by mass are added and mixed, and pressure filtration is performed to obtain the blue colored resin composition of Example 15. 15 was obtained.
  • Surfactant R08MH manufactured by DIC
  • silane coupling agent KBM503 manufactured by Shin-Etsu Silicone
  • Example 15 (1) Preparation of Coloring Material Dispersion
  • the coloring material was 9.00 parts by weight of Blue Coloring Material A of Synthesis Example 1 and 1.00 parts by weight of Pigment Violet 23 (PV23) and Synthesis Example 1
  • PB15: 6 Pigment Violet 23
  • a colorant dispersion 17 was obtained.
  • the color material dispersion 15 was changed to the color material dispersions 16 to 17, respectively, and the composition of the mixed solvent became the composition shown in Table 1-1 below. Blue colored resin compositions 16 to 17 of Examples 16 to 17 were obtained in the same manner as (2) of Example 15 except for the above changes.
  • Comparative Examples 1 to 18 (1) Preparation of Comparative Coloring Material Dispersion Solution In Example 1 (1), except that the coloring material, the dispersant, and the solvent were changed to have the compositions shown in Table 1-1 below, Comparative colorant dispersions 1 to 18 were prepared in the same manner as in 1). Among these, the colorant dispersions of Comparative Example 4 and Comparative Example 5 were gelled. (2) Preparation of Comparative Colored Resin Composition In (2) of Example 1, except that Color Material Dispersion 1 was changed to Comparative Color Material Dispersions 1 to 3 and 6 to 18, respectively (2 In the same manner as above, comparative colored resin compositions of Comparative Examples 1 to 3 and 6 to 18 were obtained.
  • Comparative Examples 21 to 26 (1) Preparation of Comparative Colorant Dispersion Solution Example 15 (1) except that the colorant, dispersant, and solvent were changed to the compositions shown in Table 1-2 below. Comparative colorant dispersions 21 to 26 were obtained in the same manner as (1). (2) Preparation of colored resin composition The procedure of (15) of Example 15 was repeated except that, instead of the color material dispersion 15, color material dispersions 21 to 26 were used. Thus, comparative blue colored resin compositions 21 to 26 of Comparative Examples 21 to 26 were obtained.
  • the substrate on which the colored film is formed is post-baked for 60 minutes in a clean oven at 230 ° C., and the chromaticity (x, y), luminance (Y), and L, a, b (L 1 ) of the obtained colored film. , A 1 , b 1 ) and contrast.
  • the contrast was measured using a “contrast meter CT-1” manufactured by Aisaka Electric.
  • Table 2-1 and Table 2-2 show the chromaticity (x, y) and luminance (Y) of the colored film after post-baking, and the color difference ( ⁇ Eab) before and after post-baking.
  • Luminance evaluation criteria Double-circle: The brightness
  • ⁇ The luminance Y was 8.8 or more and less than 9.2.
  • X Brightness Y8.0 or more and less than 8.8.
  • Xx It was less than luminance Y8.0.
  • ⁇ Eab was less than 6.0.
  • ⁇ : ⁇ Eab was 6.0 or more and less than 8.0.
  • ⁇ : ⁇ Eab was 8.0 or more and less than 10.0.
  • X: ⁇ Eab was 10.0 or more and less than 20.0.
  • XX: ⁇ Eab was 20.0 or more.
  • NMP resistance evaluation The substrate having the colored layer of the colored resin composition obtained by the above optical performance and heat resistance evaluation was immersed in N-methylpyrrolidone (NMP) heated to 80 ° C. for 10 minutes, and the dye exuded into NMP was visually observed. Confirmed. The results are shown in Table 2-1 and Table 2-2. ⁇ : NMP was not colored. X: NMP was lightly colored. XX: NMP was deeply colored.
  • NMP N-methylpyrrolidone
  • Example 15 The blue colored resin composition obtained in Example 15 and Comparative Examples 20 to 21 was applied on a glass substrate having a thickness of 0.7 mm (manufactured by Nippon Electric Glass, “OA-10G”) using a spin coater, Heat drying was performed on a hot plate at 80 ° C. for 3 minutes.
  • This colored layer was irradiated with ultraviolet rays of 40 mJ / cm 2 using a super high pressure mercury lamp through a photomask on which a stripe pattern of 80 ⁇ m lines and spaces was drawn.
  • the glass plate on which the colored layer was formed was shower-developed for 60 seconds using a 0.05% by weight aqueous potassium hydroxide solution as an alkaline developer, and further washed with ultrapure water for 60 seconds.
  • the glass substrate was arrange
  • the sublimation property was evaluated by visually confirming the presence or absence of the sublimated material on the upper glass substrate. The results are shown in Table 2-1 and Table 2-2. In Tables 2-1 and 2-2, “-” indicates that the corresponding evaluation test was not conducted.
  • the dispersant is selected from the structural unit represented by the general formula (I) and the structural unit represented by the following general formula (I ′).
  • a colored resin composition using a polymer having one or more kinds maintains a high contrast similar to that immediately after dispersion, even when a colored layer is formed after storage at 40 ° C. for 1 week, dispersibility and storage It became clear that it was excellent in stability. It was also revealed that the colored layers of Examples 1 to 9 were excellent in heat resistance.
  • Comparative Example 1 using only the solvent (1) having an SP value of 8.6 (cal / cm 3 ) 1/2 or more is a colored layer formed using the colored resin composition after storage for 1 week.

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WO2021199786A1 (ja) * 2020-04-01 2021-10-07 株式会社Ｄｎｐファインケミカル 色材分散液、分散剤、着色硬化性組成物、カラーフィルタ、表示装置

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JP6953851B2 (ja) * 2017-07-14 2021-10-27 大日本印刷株式会社 高分子分散剤及びその製造方法、色材分散液、着色樹脂組成物、カラーフィルタ、液晶表示装置、及び発光表示装置
JP7259521B2 (ja) 2018-05-09 2023-04-18 大日本印刷株式会社 色材分散液、組成物、膜、光学フィルタ、及び表示装置
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CN110249263A (zh) * 2017-03-31 2019-09-17 Dnp精细化工股份有限公司 感光性着色树脂组合物及其固化物、滤色器和显示装置
CN110249263B (zh) * 2017-03-31 2023-12-08 Dnp精细化工股份有限公司 感光性着色树脂组合物及其固化物、滤色器和显示装置
WO2021199786A1 (ja) * 2020-04-01 2021-10-07 株式会社Ｄｎｐファインケミカル 色材分散液、分散剤、着色硬化性組成物、カラーフィルタ、表示装置
JP7627547B2 (ja) 2020-04-01 2025-02-06 株式会社Ｄｎｐファインケミカル 色材分散液、分散剤、着色硬化性組成物、カラーフィルタ、表示装置

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