Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
  • C09B67/0085—Non common dispersing agents
  • C09B67/009—Non common dispersing agents polymeric dispersing agent
• • 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

Definitions

• the present invention relates to a pigment dispersion used for a color filter, a coloring composition containing the same, use of the pigment dispersion, use of the coloring composition, and a color filter manufactured using the pigment dispersion.
• a color filter used in a liquid crystal display device is manufactured by a photolithography method in which a coloring composition obtained by blending a pigment dispersion with a resin or the like is applied to a transparent substrate such as glass, and then exposed, cured, developed, and thermally cured. ing.
• the pigment dispersion used here is a non-aqueous pigment dispersion in which a pigment is dispersed in an organic solvent.
• a method for producing a non-aqueous pigment dispersion a production method using a polymer dispersant such as a graft polymer is known. In order to satisfy various required performances, improvement of the dispersant has been studied.
• Patent Document 1 has a structural unit having an ethylene oxide chain and a propylene oxide chain for the purpose of improving the wettability (affinity) between the dispersion medium and the pigment surface and achieving both pigment dispersibility and coating suitability.
• Patent Document 2 discloses that when dry aggregates are generated during coating, some of them have an amino group that forms a salt with allyl halide and / or aralkyl halide for the purpose of easily removing the dry aggregates.
• a pigment dispersion characterized by containing a block copolymer is disclosed.
• Patent Document 3 discloses a binder resin, an A block having a quaternary ammonium base in the side chain, and a quaternary ammonium for the purpose of satisfying the requirements of high permeability and high concentration and providing good coating suitability.
• a colored resin composition comprising an AB block copolymer and / or a BAB block copolymer composed of a B block having no base is disclosed.
• a pigment dispersion for a color filter comprising a pigment dispersant represented by the general formula (I), an organic pigment, and an ether organic solvent.
• R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group.
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms (where R 5 adjacent to R 1 represents a single bond), and R 6 represents an alkanediyl group having 1 to 4 carbon atoms.
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms
• R 8 represents a hydrocarbon group having 1 to 18 carbon atoms
• a represents an average addition mole number, and 1 to 100
• M 1 ) ⁇ and (M 2 ) ⁇ each independently represents an anion
• n, m, and k represent the average number of structural units, (n + m + k) is from 1 to 5, and n is from 1 to 5
• M is 0 or more and 4 or less
• k is 0 or more and 4 or less.
• a colored composition for a color filter comprising the pigment dispersion according to [1] and a binder component.
• [3] Use of the pigment dispersion according to [1] for the production of a color filter.
• [4] Use of the colored composition according to [2] for the production of a color filter.
• [5] A color filter produced using the pigment dispersion according to [1].
• the color filter is required to have a high contrast as the display image becomes higher in definition.
• the pigment is made finer.
• the viscosity of the resulting pigment dispersion and the colored composition is increased, the storage stability is also decreased, and the particle size tends to be increased.
• the color filter is manufactured by applying a colored composition prepared using a pigment dispersion to a glass substrate. A fixed matter (dried aggregate) is generated in the nozzle of this nozzle, and it is necessary to dissolve it again in a solvent and remove it.
• the present invention provides a novel color filter pigment dispersion having a small average particle size, low viscosity, excellent storage stability and good redispersibility, a coloring composition containing the same, and a pigment dispersion. It is an object of the present invention to provide a color filter produced by using the pigment dispersion, the use of the coloring composition, and the pigment dispersion.
• the present inventors can solve the above problems by using a pigment dispersant represented by the following general formula (I) (hereinafter also referred to as “the pigment dispersant of the present invention”) in a pigment dispersion for a color filter. I found.
• a pigment dispersant represented by the following general formula (I) hereinafter also referred to as “the pigment dispersant of the present invention”
• a pigment dispersion for a color filter comprising a pigment dispersant represented by the general formula (I), an organic pigment, and an ether organic solvent.
• R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group.
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms (where R 5 adjacent to R 1 represents a single bond), and R 6 represents an alkanediyl group having 1 to 4 carbon atoms.
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms
• R 8 represents a hydrocarbon group having 1 to 18 carbon atoms
• a represents an average addition mole number, and 1 to 100
• M 1 ) ⁇ and (M 2 ) ⁇ each independently represents an anion
• n, m, and k represent the average number of structural units, (n + m + k) is from 1 to 5, and n is from 1 to 5
• M is 0 or more and 4 or less
• k is 0 or more and 4 or less.
• a colored composition for a color filter comprising the pigment dispersion according to [1] and a binder component.
• [3] Use of the pigment dispersion according to [1] for the production of a color filter.
• [4] Use of the colored composition according to [2] for the production of a color filter.
• [5] A color filter produced using the pigment dispersion according to [1].
• a novel pigment dispersion for a color filter having a small average particle size, low viscosity, excellent storage stability, and good redispersibility a coloring composition containing the same, and a pigment dispersion , The use of a coloring composition, and a color filter produced using the pigment dispersion.
• the pigment dispersion for a color filter of the present invention contains a pigment dispersant represented by the general formula (I), an organic pigment, and an ether organic solvent.
• the reason why the pigment dispersion of the present invention has a small average particle diameter, low viscosity, excellent storage stability, and good redispersibility is not clear, but is considered as follows.
• the pigment dispersion of the present invention includes a pigment having a specific structure and having an alkoxypolyalkylene glycol group having high solvent affinity and a quaternary ammonium group capable of maintaining strong adsorptivity on the pigment surface for a long period of time. Contains a dispersant. Since the alkoxypolyalkylene glycol group of the pigment dispersant spreads in the ether organic solvent, a strong repulsive force is generated between the organic pigment particles in the pigment dispersion.
• the quaternary ammonium group is strongly adsorbed on the surface of the organic pigment and maintains its strong adsorptivity for a long time. Therefore, it is considered that the pigment dispersant of the present invention is hardly detached from the pigment surface despite having a high affinity for a solvent. Therefore, by using the pigment dispersant of the present invention, it is excellent in atomizing the pigment at the time of dispersion. Is considered to maintain excellent dispersibility.
• the dispersant contained in the pigment dispersion of the present invention has a number of nitrogen (that is, (n + m + k) in the general formula (I)).
• Number) and the number of quaternary ammonium groups bonded to the dispersing group can be small and precisely controlled. Therefore, it is considered that the adsorption loss with respect to the pigment is reduced and not only the dispersibility and the dispersion stability are excellent, but also the bridging aggregation when the pigments are close to each other at the time of drying.
• the colored composition for a color filter of the present invention when continuously applied to a glass substrate, it suppresses the occurrence of fixed matter (dry aggregate) in a nozzle such as a coater due to drying of the colored composition, and the dried product is Even when it occurs, it is considered that the redispersibility in a solvent is high and it has good coating properties.
• a nozzle such as a coater
• the redispersibility in a solvent is high and it has good coating properties.
• the pigment dispersant used in the present invention is a compound represented by the following general formula (I).
• R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group.
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms (where R 5 adjacent to R 1 represents a single bond),
• R 6 represents an alkanediyl group having 1 to 4 carbon atoms,
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms,
• R 8 represents a hydrocarbon group having 1 to 18 carbon atoms, a represents an average addition mole number, and 1 to 100
• (M 1) - and (M 2) - each independently represent an anion, n, m, k represents the average number of structural units, (n + m + k) is 1 to 5, n is 1 or more 5 or less, m is 0 or more and 4 or less, and k is 0 or more and 4 or less.
• R 7 Os When a plurality of R 7 Os are present, they may be the same or different, and the structural units may be in any arrangement order.
• (N + m + k) is 5 or less from the viewpoint of dispersibility and redispersibility, preferably 4 or less, more preferably 3 or less, still more preferably 2.5 or less, still more preferably 2.2 or less, From the viewpoints of dispersibility, storage stability and redispersibility, it is preferably 1.5 or more, more preferably 1.8 or more, and still more preferably 2 or more.
• (N + m + k) is more preferably 2 from the viewpoints of excellent dispersibility, storage stability, and redispersibility.
• n is 5 or less from the viewpoint of dispersibility and redispersibility, preferably 4 or less, more preferably 3 or less, still more preferably 2.5 or less, and still more preferably 2.2 or less.
• N is more preferably 2 from the viewpoint of excellent dispersibility, storage stability and redispersibility.
• m is 4 or less, preferably 3 or less, more preferably 2 or less, still more preferably 1.5 or less, and even more preferably 1.3 or less.
• m is 4 or less, preferably 0.5 or more, more preferably 0.8 or more.
• it is preferably 0.5 or less, more preferably 0.2 or less, and still more preferably 0.
• k is 4 or less from the viewpoint of dispersibility, storage stability and redispersibility, preferably 3 or less, more preferably 2 or less, still more preferably 1.5 or less, and still more preferably 1.2 or less. From the viewpoint of storage stability, it is 0 or more, and from the viewpoint of high dispersibility and redispersibility, it is preferably 0.5 or less, more preferably 0.2 or less, and still more preferably 0.
• the ratio of n to (n + m + k) (n / (n + m + k)) is preferably 0.3 or more, more preferably 0.6 or more, still more preferably 0.8 or more, from the viewpoints of dispersibility and storage stability.
• the average number of structural units, n, m, k, (n + m + k) can be measured, for example, by the method described in the examples.
• the structural units whose average number of structural units is indicated by n, m, and k may be in any arrangement order. When one or more of n, m, and k are plural, each structural unit may be in any arrangement order such as random or block.
• R 1 , R 2 , and R 4 have 10 or less carbon atoms, preferably 8 or less, more preferably 6 or less, and even more preferably 1. .
• R 1 , R 2 , and R 4 are preferably hydrocarbon groups not substituted with a hydroxyl group. Specific examples of R 1 , R 2 , and R 4 include at least one selected from a methyl group, an ethyl group, a butyl group, a hexyl group, a hydroxymethyl group, a hydroxybutyl group, and a hydroxyhexyl group.
• R 1 and R 2 are preferably a hydrocarbon group having 1 to 10 carbon atoms, or a hydroxyalkyl group having 2 to 6 carbon atoms, a hydrocarbon group having 1 to 5 carbon atoms, or 3 to 6 carbon atoms.
• the hydroxyalkyl group is more preferably a hydrocarbon group having 1 to 3 carbon atoms or a hydroxyalkyl group having 4 to 6 carbon atoms.
• the carbon number of R 4 is preferably 4 or less, more preferably 3 or less.
• R 4 is preferably a methyl group or an ethyl group, and more preferably a methyl group.
• the carbon number of the alkanediyl group of R 5 is 1 or more from the viewpoint of dispersibility and storage stability, preferably 2 or more, more preferably 3 or more from the viewpoint of dispersibility, storage stability and redispersibility. From the viewpoint of dispersibility, it is 18 or less, preferably 14 or less, more preferably 12 or less, still more preferably 10 or less, and from the viewpoint of dispersibility and redispersibility, even more preferably 6 or less. is there.
• alkanediyl group of R 5 examples include at least one selected from a methylene group, an ethylene group, various propanediyl groups, various hexanediyl groups, various octanediyl groups, and various nonanediyl groups.
• Dispersibility and storage stability From the viewpoint of properties, it is preferably at least one selected from a propane-1,3-diyl group, a hexane-1,6-diyl group, and a nonane-1,9-diyl group, and is suitable for dispersibility, storage stability, From the viewpoint of dispersibility, at least one selected from a propane-1,3-diyl group and a hexane-1,6-diyl group is more preferable, and a hexane-1,6-diyl group is more preferable.
• the carbon number of R 6 is 4 or less, preferably 3 or less, more preferably 2 or less, and still more preferably 1 from the viewpoint of ease of production of the pigment dispersant of the present invention.
• R 6 is preferably a methylene group.
• the carbon number of R 7 is 4 or less, preferably 3 or less, or 2 or more from the viewpoints of dispersibility, storage stability, and redispersibility.
• R 7 is preferably at least one selected from an ethylene group and a propylene group.
• a is 1 or more from the viewpoints of dispersibility, storage stability and redispersibility, preferably 15 or more, more preferably 21 or more, more preferably 30 or more, still more preferably 40 or more, and 100 Or less, preferably 95 or less, more preferably 70 or less, and still more preferably 50 or less.
• (R 7 O) When a plurality of (R 7 O) are present, they may be the same or different, and the sequence of (R 7 O) may be either random or block.
• (R 7 O) preferably includes a structural unit derived from propylene oxide, and preferably includes a structural unit derived from propylene oxide and a structural unit derived from ethylene oxide, from the viewpoint of affinity with an ether-based organic solvent. .
• (R 7 O) a is preferably a structural unit represented by the following general formula (Ia) from the viewpoint of dispersibility and storage stability.
• PO represents a propylene oxide unit
• EO represents an ethylene oxide unit
• b and c represent average added mole numbers
• b is 0 or more and 100 or less
• c is 0 or more and 100 or less.
• Yes, b + c is 1 or more and 100 or less.
• * represents a binding site.
• the structural unit is preferably a block polymer, more preferably a diblock polymer
• the (PO) terminal side of the formula (Ia) is R 8.
• b is preferably 11 or more, more preferably 15 or more, still more preferably 21 or more, and even more preferably 25 or more. From the viewpoint of property, it is preferably 60 or less, more preferably 50 or less, and still more preferably 35 or less.
• c is preferably 1 or more, more preferably 5 or more, still more preferably 11 or more, and still more preferably 15 or more from the viewpoint of dispersibility, storage stability, and ease of manufacture.
• solubility in the organic solvent it is preferably 95 or less, more preferably 70 or less, still more preferably 50 or less, still more preferably 30 or less, and still more preferably 20 or less.
• the total of b and c (b + c) is preferably 15 or more, more preferably 21 or more, more preferably 30 or more, still more preferably 40 or more, from the viewpoints of dispersibility, storage stability, and redispersibility.
• the ratio of b to the total of b and c (b / (b + c)) is preferably 0.2 or more, more preferably 0.4 or more, and still more preferably from the viewpoints of dispersibility, storage stability and redispersibility. In addition, from the viewpoint of dispersibility and manufacturability, it is preferably 0.97 or less, more preferably 0.86 or less, and still more preferably 0.8 or less.
• the carbon number of R 8 is 1 or more from the viewpoint of dispersibility and redispersibility, preferably 6 or more, more preferably 10 or more, and 18 or less from the viewpoint of dispersibility and storage stability. Yes, preferably 16 or less, more preferably 14 or less, and still more preferably 12 or less.
• R 8 is preferably at least one selected from an aliphatic hydrocarbon group and an aromatic hydrocarbon group which may have an aliphatic hydrocarbon group from the viewpoints of dispersibility, storage stability and redispersibility, An aliphatic hydrocarbon group is more preferable, and at least one selected from an alkyl group and an alkenyl group is further preferable.
• R 8 is at least one selected from a methyl group, an ethyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, an oleyl group, a stearyl group, a phenyl group, a p-octylphenyl group, and a p-nonylphenyl group.
• it is at least one selected from a methyl group, an ethyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, an oleyl group, a stearyl group, and a phenyl group, and more preferably a methyl group, At least one selected from a decyl group, a lauryl group, and a phenyl group, and from the viewpoint of redispersibility, preferably at least one selected from a phenyl group, a decyl group, and a lauryl group, dispersibility and storage stability In view of the above, it is preferably at least one selected from a methyl group, a decyl group, and a lauryl group, and has excellent dispersion From the viewpoint of storage stability and redispersibility, more preferably decyl group or a lauryl group, more preferably a lauryl group.
• the carbon number of R 3 is 10 or less from the viewpoint of dispersibility and storage stability, preferably 7 or less, more preferably 4 or less, still more preferably 2 or less, and 1 or more.
• R 3 include at least one selected from a methyl group, an ethyl group, a propyl group, and a benzyl group, and a methyl group is preferable from the viewpoint of high dispersibility and storage stability.
• (M 1 ) ⁇ and (M 2 ) ⁇ are each independently an anion, and are preferably a halide ion, an alkyl sulfate ion, an alkyl benzene sulfonate ion, and the like from the viewpoints of dispersibility, storage stability and ease of production. It is one selected from alkyl carbonate ions.
• (M 1 ) ⁇ is preferably at least one selected from halide ions, more preferably chloride ions, bromide ions, and iodide ions from the viewpoints of dispersibility, storage stability, and ease of production. More preferred is chloride ion.
• (M 2 ) ⁇ is preferably at least one selected from CH 3 SO 4 ⁇ , C 2 H 5 SO 4 — and CH 3 C 6 H 4 SO 3 — Preferably, it is at least one selected from CH 3 SO 4 — and C 2 H 5 SO 4 — , and more preferably CH 3 SO 4 — .
• (M 2 ) ⁇ is preferably a halide ion, more preferably at least one selected from a chloride ion, a bromide ion, and an iodide ion from the viewpoints of dispersibility and storage stability. More preferred is chloride ion.
• m and k are preferably 0 from the viewpoint of dispersibility and storage stability. More specifically, the pigment dispersant of the present invention is represented by the following general formula (I-1). Compounds are preferred.
• R 1 , R 2 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group;
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms,
• R 6 represents an alkanediyl group having 1 to 4 carbon atoms,
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms,
• R 8 Represents a hydrocarbon group having 1 to 18 carbon atoms, a represents an average addition mole number, 1 to 100, (M 1 ) ⁇ represents an anion, n represents an average number of structural units, 1 It is 5 or less.
• R 7 Os When a plurality of R 7 Os
• n is 5 or less from the viewpoint of dispersibility and redispersibility, preferably 4 or less, more preferably 3 or less, still more preferably 2.5 or less, and still more preferably 2 .2 or less, and from the viewpoint of dispersibility, storage stability and redispersibility, it is 1 or more, preferably 1.5 or more, more preferably 1.7 or more, and still more preferably 2 or more.
• N is more preferably 2 from the viewpoint of excellent dispersibility, storage stability and redispersibility.
• the weight average molecular weight of the pigment dispersant is preferably 2,000 or more, more preferably 3,000 or more, still more preferably 3,500 or more, from the viewpoints of dispersibility, storage stability, and redispersibility. Preferably it is 35,000 or less, More preferably, it is 20,000 or less, More preferably, it is 10,000 or less.
• the measuring method of a weight average molecular weight is based on the method as described in an Example.
• the pigment dispersant used in the present invention is obtained, for example, by a reaction between a halogenated alkyl ester compound represented by the following general formula (II) and a polyamine compound represented by the following general formula (III).
• a halogenated alkyl ester compound represented by the following general formula (II) R 6 , R 7 , R 8 and a are the same as those described above, and X represents a halogen atom.
• R 1 , R 2 , R 4 , R 5 and (n + m + k) are the same as those described above.
• the pigment dispersant of this invention represented by general formula (I) is obtained by making the said raw material react in a solvent-free or solvent.
• the solvent used in the reaction is preferably, for example, an ether organic solvent used in the present invention described later.
• the ether organic solvent is preferably (poly) alkylene glycol monoalkyl ether acetate, more preferably propylene glycol monomethyl ether acetate (hereinafter also referred to as “PGMEA”), diethylene glycol monobutyl ether acetate (hereinafter also referred to as “BCA”), photo From the viewpoint of easy handling and workability of the pigment dispersion in the lithography method, PGMEA is more preferable.
• halogenated alkyl ester represented by the general formula (II)
• an alcohol having an R 8 hydrocarbon group and an alkylene oxide compound forming R 7 O are reacted in the presence of a basic substance.
• alkoxy represents R 8 O— (R 8 represents the above-described hydrocarbon group).
• the polyamine compound represented by the general formula (III) is, for example, a method of reacting an alkylene diol with a primary amine or a secondary amine in the presence of a Cu-Ni catalyst, or a reductive alkylation of an alkylene diamine with an aldehyde. Can be obtained by the following method.
• N, N, N ′, N′-tetramethylhexanediamine (“Caorizer No. 1” manufactured by Kao Corporation)
• N, N, N ′, N′-tetramethylpropanediamine Kao Riser No. 2 ”manufactured by Kao Corporation
• polyamine glycol Kaor Riser P200 ”manufactured by Kao Corporation
• the general number of amine functional groups of the polyamine compound represented by the general formula (III) ((n + m + k) ⁇ mol amount in the general formula (III))
• the ratio of the halogenated alkyl ester compound (molar amount) represented by the formula (II) can be appropriately set according to the target compound, and is, for example, 0.3 to 1.2. By appropriately setting the ratio, a compound in which the numbers of n and m with respect to (n + m + k) in general formula (I) are adjusted can be obtained.
• the reaction amount ratio between the polyamine compound and the halogenated alkyl ester compound is a molar equivalent calculated from the amine value of the polyamine compound and the halogenated alkyl ester compound from the viewpoint of more accurately controlling the number of n and m. It is preferable to adjust based on the molar equivalent calculated from the amount of halogen.
• the reaction atmosphere in the said process is inert gas atmosphere, such as nitrogen gas atmosphere and argon.
• the temperature of the reaction in this step is, for example, preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and preferably 100 ° C. or lower.
• a compound in which k exceeds 0 can be obtained, for example, by treating a compound in general formula (I) with m exceeding 0 with a quaternizing agent.
• a quaternizing agent a substance that reacts with a tertiary amino group to convert the amino group to quaternary ammonium is used, and examples thereof include dialkyl sulfate, alkyl halide, and alkyl p-toluenesulfonate.
• dialkyl sulfate include dimethyl sulfate and diethyl sulfate.
• the alkyl halide include methyl chloride, methyl iodide, and benzyl chloride.
• the p-toluenesulfonate examples include methyl p-toluenesulfonate, p. -Ethyl toluenesulfonate and the like. Dialkyl sulfate is preferred, dimethyl sulfate and diethyl sulfate are more preferred, and dimethyl sulfate is particularly preferred.
• the reaction atmosphere in the said process is inert gas atmosphere, such as nitrogen gas atmosphere and argon.
• the temperature of the reaction in this step depends on the kind of the quaternizing agent, it is preferably 50 ° C. or higher, preferably 80 or higher from the viewpoint of promoting the reaction, and preferably 100 ° C. or lower.
• the organic pigment used in the present invention (hereinafter also simply referred to as “pigment”) is preferably used for color filters, and examples thereof include azo pigments, phthalocyanine pigments, condensed polycyclic pigments, lake pigments, and the like.
• azo pigment C.I. I. Insoluble azo pigments such as CI Pigment Red 3; I. Soluble red azo pigments such as CI Pigment Red 48: 1; I. And condensed azo pigments such as CI Pigment Red 144.
• the phthalocyanine pigment include C.I. I. A copper phthalocyanine pigment such as CI Pigment Blue 15: 6; I.
• CI Pigment Green 58 zinc phthalocyanine pigments such as CI Pigment Green 58.
• the condensed polycyclic pigment include C.I. I. Anthraquinone pigments such as CI Pigment Red 177; I. Perylene pigments such as CI Pigment Red 123; I. Perinone pigments such as C.I. Pigment Orange 43; I. Quinacridone pigments such as C.I. Pigment Red 122; I. Dioxazine pigments such as CI Pigment Violet 23, C.I. I. Pigment Yellow 109 and other isoindolinone pigments, C.I. I. Pigment Orange 66 and other isoindoline pigments, C.I. I.
• Quinophthalone pigments such as CI Pigment Yellow 138; I. Pigment azo complex pigments such as CI Pigment Yellow 150, C.I. I. Indigo pigments such as CI Pigment Red 88; I. Metal complex pigments such as C.I. Pigment Green 8; I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. And diketopyrrolopyrrole pigments such as CI Pigment Orange 71.
• a diketopyrrolopyrrole pigment represented by the following general formula (1) is preferable from the viewpoint of more effectively expressing the effects of the present invention.
• X 1 and X 2 each independently represent a hydrogen atom or a halogen atom
• Y 1 and Y 2 each independently represent a hydrogen atom or a —SO 3 H group.
• the halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom.
• Suitable examples of commercially available diketopyrrolopyrrole pigments include BASF Corporation C.I. I.
• Pigment Red 254 trade names "Irgaphor Red B-CF”, “Irgaphor Red BK-CF”, “Irgaphor Red BT-CF”, “Irgazin DPP Red BO”, “Irgazin DPP Red BL”, “Cromophtal DPP Red BP” , “Cromophtal DPP Red BOC” and the like.
• the organic pigment from the viewpoint of improving the brightness Y value, it is desirable to use an atomized product having an average primary particle size of preferably 100 nm or less, more preferably 20 to 60 nm.
• the average primary particle diameter of the organic pigment can be determined by a method of directly measuring the size of primary particles from an electron micrograph.
• the short axis diameter and the long axis diameter of each primary particle are measured, and the average value thereof is defined as the particle diameter of the particle.
• the volume of each particle is expressed as one side of the particle diameter.
• the volume average particle diameter is obtained by approximating to the cube as described above, and this is used as the average primary particle diameter.
• Said organic pigment can be used individually or in combination of 2 or more types.
• the surface of the organic pigment is pretreated with a resin, polymer, pigment derivative, or the like. Can also be used.
• the pigment dispersion of the present invention improves the dispersibility of the pigment and enhances the compatibility with the binder component used in the color filter, and from the viewpoint of achieving both substrate adhesion and developability of the resulting cured film.
• the viscosity of the ether organic solvent at 25 ° C. is preferably 0.8 mPa ⁇ s or more, more preferably 0.9 mPa ⁇ s or more, and 1.0 mPa ⁇ s from the viewpoint of easy handling of the pigment dispersion and the colored composition.
• s or more is more preferable, and from the viewpoint of improving the contrast of the cured film using the pigment dispersion and facilitating coating of the colored composition, 5.0 mPa ⁇ s or less is preferable, and 3.5 mPa ⁇ s is preferable. The following is more preferable, and 2.0 mPa ⁇ s or less is more preferable. From the viewpoint of improving the contrast of the cured film obtained by increasing the SP value of the ether-based organic solvent, the moderate affinity with the pigment surface, low surface tension, compatibility with the binder component used in the color filter, and the like are improved.
• the boiling point of the ether-based organic solvent is preferably 50 ° C. or higher, more preferably 100 ° C. or higher, still more preferably 120 ° C. or higher, and from the viewpoint of ease of removal by drying the coating film, 300 degrees C or less is preferable, 260 degrees C or less is more preferable, and 200 degrees C or less is still more preferable.
• (poly) alkylene glycol monoalkyl ether acetate, (poly) alkylene glycol monoalkyl ether propionate and (poly) alkylene glycol dialkyl ether are preferred, and (poly) alkylene glycol monoalkyl ether acetate is more preferred. preferable.
• (poly) alkylene glycol means at least one selected from alkylene glycol and polyalkylene glycol.
• Examples of (poly) alkylene glycol monoalkyl ether acetate include ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monoethyl ether acetate, diethylene glycol Monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate (BCA) and the like are mentioned.
• PGMEA (boiling point: 146 ° C., viscosity at 25 ° C .: 1.1 mPa ⁇ s, SP value: 8.73), BCA (boiling point: 247 ° C, viscosity at 25 ° C: 3.1) Pa ⁇ s, SP value: 8.94) is preferred, PGMEA is more preferable.
• Examples of (poly) alkylene glycol monoalkyl ether propionate include ethylene glycol monomethyl ether propionate, ethylene glycol monoethyl ether propionate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether propionate, etc. Is mentioned.
• Examples of (poly) alkylene glycol dialkyl ethers include dipropylene glycol dimethyl ether and dipropylene glycol methyl propyl ether.
• the method for producing a pigment dispersion of the present invention preferably includes the following steps from the viewpoint of producing a pigment dispersion for a color filter having a small average particle size, low viscosity, and excellent storage stability.
• dispersers can be used as the mixing disperser used for dispersion.
• examples thereof include high-speed stirring and mixing devices such as homomixers, kneaders such as roll mills, kneaders and extruders, high-pressure dispersers such as high-pressure homogenizers, media-type dispersers such as paint shakers and bead mills. These devices can be used in combination.
• a high-speed stirring and mixing device such as a homomixer, and a media type dispersing machine such as a paint shaker or a bead mill are preferable.
• the material of the media used in the dispersion step is preferably a ceramic material such as zirconia or titania, a polymer material such as polyethylene or nylon, a metal, or the like, and zirconia is preferred from the viewpoint of wear.
• the diameter of the media is preferably 0.003 mm or more, more preferably 0.01 mm or more, and preferably 0.5 mm or less, more preferably from the viewpoint of crushing the aggregated particles in the organic pigment. 0.4 mm or less.
• the dispersion time is preferably 0.3 hours or more from the viewpoint of sufficiently miniaturizing the organic pigment, more preferably 1 hour or more, and preferably 200 hours or less from the viewpoint of production efficiency of the pigment dispersion, 50 hours. The following is more preferable.
• the dispersion method in the dispersion step of the present production method may be to obtain the desired pigment dispersion by one dispersion of the mixture, but after the mixture is predispersed using a medium, further from the preliminary dispersion step. It is preferable to carry out the main dispersion using a small medium from the viewpoint of obtaining a finer and more uniform pigment dispersion.
• the above-mentioned various dispersing machines can be used as the mixing and dispersing machine used for the preliminary dispersion, but a media type dispersing machine such as a paint shaker or a bead mill is preferable from the viewpoint of uniformly mixing the organic pigment in the ether organic solvent. .
• the diameter of the media used in the preliminary dispersion step is preferably 0.1 mm or more, more preferably 0.5 mm or less, and even more preferably 0.4 mm or less from the viewpoint of crushing the aggregated particles in the organic pigment.
• the dispersion time in the preliminary dispersion step is preferably 0.1 hour or more, more preferably 0.5 hour or more, further preferably 1 hour or more, from the viewpoint of crushing the aggregated particles in the organic pigment, and the pigment dispersion From the viewpoint of the production efficiency, it is preferably 10 hours or less, more preferably 5 hours or less, and still more preferably 4 hours or less.
• This dispersion is a step of dispersing the preliminary dispersion obtained in the preliminary dispersion, and is performed to further refine the mixture obtained in the preliminary dispersion step. From the viewpoint of miniaturizing the organic pigment, It is preferable to use a media-type disperser, and the above-described high-pressure disperser may be used in combination.
• the diameter of the media used in this dispersion step is preferably less than 0.1 mm, more preferably 0.08 mm or less, further preferably 0.07 mm or less, from the viewpoint of miniaturizing the organic pigment, and the viewpoint of separating the media from the pigment. Therefore, 0.003 mm or more is more preferable, and 0.01 mm or more is still more preferable.
• the dispersion time of this dispersion is preferably 2 hours or more, more preferably 3 hours or more from the viewpoint of sufficiently miniaturizing the organic pigment, and 200 hours or less is preferable from the viewpoint of production efficiency of the pigment dispersion, and 50 hours. The following is more preferable.
• the content of the organic pigment in the pigment dispersion of the present invention is preferably 3% by mass or more, more preferably 5% by mass or more from the viewpoint of obtaining good colorability, and 12% by mass or more from the viewpoint of improving redispersibility. Further, from the viewpoint of reducing the average particle size in the pigment dispersion and obtaining a pigment dispersion having a low viscosity, it is preferably 30% by mass or less, more preferably 20% by mass or less, and 16% by mass or less. Further preferred.
• the mass ratio of the pigment dispersant to the pigment in the pigment dispersion of the present invention is preferably 0.2 or more from the viewpoint of improving the storage stability of the pigment dispersion and improving the contrast, 0.3 or more is preferable, 0.4 or more is more preferable, and 0.6 or more is more preferable from the viewpoint of improving redispersibility. Further, from the viewpoint of increasing the blending amount of the binder component and improving the physical properties of the dried coating film, 1.5 or less is preferable, 1.2 or less is more preferable, 0.9 or less is more preferable, and 0.5 or less is further preferable.
• the content of the ether-based organic solvent in the pigment dispersion of the present invention is preferably 20% by mass or more, more preferably 40% by mass or more, still more preferably 60% by mass or more, from the viewpoint of reducing the viscosity of the dispersion. Moreover, 95 mass% or less is preferable from a viewpoint of obtaining favorable coloring property, and 90 mass% or less is more preferable.
• the average particle size in the pigment dispersion of the present invention is preferably 200 nm or less, more preferably 100 nm or less, still more preferably 90 nm or less, still more preferably 70 nm or less, in order to obtain a good contrast as a color material for a color filter. 60 nm or less is more preferable, and 20 nm or more is preferable.
• the average particle size is measured by the method described in the examples.
• the viscosity (20 ° C.) at a pigment concentration of 10 mass% of the pigment dispersion of the present invention is preferably 1 mPa ⁇ s or more, more preferably 2 mPa ⁇ s or more, and more preferably 3 mPa ⁇ s in order to obtain a favorable viscosity as a color material for a color filter.
• -More than s is more preferable, 200 mPa * s or less is preferable, 50 mPa * s or less is more preferable, 10 mPa * s or less is further more preferable, 7 mPa * s or less is still more preferable.
• the viscosity is measured by the method described in the examples.
• the coloring composition for a color filter of the present invention contains the pigment dispersion of the present invention and a binder component.
• the binder component include alkali-soluble resins, polyfunctional monomers having a plurality of polymerizable groups, and photopolymerization initiators activated by ionizing radiation.
• the alkali-soluble resin those generally used for negative resists can be used.
• a resin having an acid group is preferable from the viewpoint of solubility in an aqueous alkali solution, and a resin that is soluble in a 0.05 mass% tetramethylammonium hydroxide aqueous solution at 20 ° C at 1 mass% or more is preferable.
• the alkali-soluble resin preferably include a copolymer of (meth) acrylic acid ester and (meth) acrylic acid from the viewpoint of maintaining the dispersion of the pigment in the cured film and improving the contrast.
• a copolymer of alkyl acrylate or benzyl (meth) acrylate and (meth) acrylic acid is more preferred, and a copolymer of benzyl (meth) acrylate and (meth) acrylic acid is more preferred.
• the copolymerization ratio (molar ratio) of (meth) acrylic acid ester and (meth) acrylic acid is preferably 97/3 to 50/50, and more preferably 95/5 to 60/40.
• the weight average molecular weight of the alkali-soluble resin is preferably 5,000 or more and 50,000 or less.
• the content of the alkali-soluble resin is preferably 10% by mass or more and 40% by mass or less in the effective component excluding the solvent of the color filter coloring composition.
• polyfunctional monomer examples include (meth) acrylic acid esters having two or more ethylenically unsaturated double bonds (for example, compounds obtained by esterifying a plurality of hydroxyl groups of polyhydric alcohol with acrylic acid), urethane (meta ) Acrylate, (meth) acrylic acid amide, allyl compound, vinyl ester and the like.
• an acrylate ester having two or more ethylenically unsaturated double bonds is preferable, and dipentaerythritol hexaacrylate is more preferable.
• the content of the polyfunctional monomer is preferably 5% by mass or more and 30% by mass or less in the effective content excluding the solvent of the color filter coloring composition.
• photopolymerization initiator examples include aromatic ketones, lophine dimers, benzoin, benzoin ethers, polyhalogens and the like.
• a photopolymerization initiator a combination of 4,4′-bis (diethylamino) benzophenone and 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 4- [pN, N-di (ethoxy) is used.
• the content of the photopolymerization initiator is preferably 0.2% by mass or more and 20% by mass or less in an effective amount excluding the solvent of the color filter coloring composition.
• binder component examples include polyfunctional oligomers, monofunctional monomers, and sensitizers in addition to the above.
• Binder components such as the alkali-soluble resin, polyfunctional monomer, photopolymerization initiator, polyfunctional oligomer, monofunctional monomer, and sensitizer can be used alone or in combination of two or more.
• the content of the binder component is preferably 20% by mass or more and 80% by mass or less in the effective component excluding the solvent of the color filter coloring composition.
• the present invention further discloses the following pigment dispersion for color filter, coloring composition for color filter, use of pigment dispersion, use of coloring composition, and method for producing pigment dispersion for color filter. .
• a pigment dispersion for a color filter comprising a pigment dispersant represented by the general formula (I), an organic pigment, and an ether organic solvent.
• R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group.
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms (where R 5 adjacent to R 1 represents a single bond), and R 6 represents an alkanediyl group having 1 to 4 carbon atoms.
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms
• R 8 represents a hydrocarbon group having 1 to 18 carbon atoms
• a represents an average addition mole number, and 1 to 100
• M 1 ) ⁇ and (M 2 ) ⁇ each independently represents an anion
• n, m, and k represent the average number of structural units, (n + m + k) is from 1 to 5, and n is from 1 to 5
• M is 0 or more and 4 or less
• k is 0 or more and 4 or less.
• R 1 , R 2 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group;
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms,
• R 6 represents an alkanediyl group having 1 to 4 carbon atoms,
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms,
• R 8 Represents a hydrocarbon group having 1 to 18 carbon atoms, a represents an average addition mole number, 1 to 100, (M 1 ) ⁇ represents an anion, n represents an average number of structural units, 1 It is 5 or less.
• R 7 Os When a plurality of R 7 Os are present, they may be the same or different.
• ⁇ 3> (n + m + k) is 5 or less, preferably 4 or less, more preferably 3 or less, still more preferably 2.5 or less, still more preferably 2.2 or less, and preferably 1.5 or more.
• n is 5 or less, preferably 4 or less, more preferably 3 or less, still more preferably 2.5 or less, still more preferably 2.2 or less, and 1 or more, preferably 1
• ⁇ 5> m is 4 or less, preferably 3 or less, more preferably 2 or less, still more preferably 1.5 or less, still more preferably 1.3 or less, and 0 or more, preferably 0.5.
• ⁇ 6> The pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 5>, wherein m is preferably 0.5 or less, more preferably 0.2 or less, and still more preferably 0.
• k is 4 or less, preferably 3 or less, more preferably 2 or less, further preferably 1.5 or less, further preferably 1.2 or less, and 0 or more.
• ⁇ 1> to ⁇ 6> The pigment dispersion for a color filter according to any one of 6).
• ⁇ 8> The pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 7>, wherein k is preferably 0.5 or less, more preferably 0.2 or less, and still more preferably 0.
• the ratio of n to (n + m + k) (n / (n + m + k)) is preferably 0.3 or more, more preferably 0.6 or more, still more preferably 0.8 or more, and even more preferably 0.9.
• R 1 , R 2 , and R 4 are preferably at least one selected from a methyl group, an ethyl group, a butyl group, a hexyl group, a hydroxymethyl group, a hydroxybutyl group, and a hydroxyhexyl group,
• R 1 and R 2 are preferably a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyalkyl group having 2 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 5 carbon atoms, Or a hydroxyalkyl group having 3 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 3 carbon atoms, or a hydroxyalkyl group having 4 to 6 carbon atoms, ⁇ 1> to ⁇ 12>
• ⁇ 14> The pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 13>, wherein R 4 has preferably 4 or less, more preferably 3 or less.
• R 4 is preferably a methyl group or an ethyl group, and more preferably a methyl group.
• the carbon number of the alkanediyl group of R 5 is 1 or more, preferably 2 or more, more preferably 3 or more, and 18 or less, preferably 14 or less, more preferably 12 or less,
• the alkanediyl group of R 5 is preferably at least one selected from a methylene group, an ethylene group, various propanediyl groups, various hexanediyl groups, various octanediyl groups, and various nonanediyl groups, preferably propane- At least one selected from a 1,3-diyl group, a hexane-1,6-diyl group, and a nonane-1,9-diyl group, more preferably a propane-1,3-diyl group and a hexane-1,
• the pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 16>, which is at least one selected from 6-diyl groups, and more preferably a hexane-1,6-diyl group.
• ⁇ 18> The color filter pigment according to any one of ⁇ 1> to ⁇ 17>, wherein R 6 has 4 or less carbon atoms, preferably 3 or less, more preferably 2 or less, and still more preferably 1.
• ⁇ 19> The pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 18>, wherein R 7 has 4 or less carbon atoms, preferably 3 or less, and 2 or more.
• R 7 is preferably at least one selected from an ethylene group and a propylene group.
• ⁇ 21> (R 7 O) preferably includes a structural unit derived from propylene oxide, more preferably includes a structural unit derived from ethylene oxide and a structural unit derived from propylene oxide.
• the pigment dispersion for a color filter as described. ⁇ 22> a is 1 or more, preferably 15 or more, more preferably 21 or more, more preferably 30 or more, still more preferably 40 or more, and 100 or less, preferably 95 or less, more preferably
• ⁇ 23> (R 7 O) a is a pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 22>, preferably a structural unit represented by the following general formula (Ia).
• PO represents a propylene oxide unit
• EO represents an ethylene oxide unit
• b and c represent average added mole numbers
• b is 0 or more and 100 or less
• c is 0 or more and 100 or less
• b + c is 1 or more and 100 or less.
• * Represents a binding site.
• the (PO) terminal side of the formula (Ia) is preferably bonded to R 8 O and the (EO) terminal side is preferably bonded to a carbonyl group.
• Pigment dispersion. ⁇ 26> b is preferably 11 or more, more preferably 15 or more, still more preferably 21 or more, still more preferably 25 or more, and is preferably 60 or less, more preferably 50 or less, still more preferably 35 or less.
• the sum of b and c (b + c) is preferably 15 or more, more preferably 21 or more, more preferably 30 or more, still more preferably 40 or more, and preferably 95 or less, more preferably 70 or less.
• the ratio of b to the total of b and c (b / (b + c)) is preferably 0.2 or more, more preferably 0.4 or more, still more preferably 0.5 or more, and preferably
• the carbon number of R 8 is 1 or more, preferably 6 or more, more preferably 10 or more, and 18 or less, preferably 16 or less, more preferably 14 or less, and still more preferably 12.
• R 8 is preferably at least one selected from an aliphatic hydrocarbon group and an aromatic hydrocarbon group which may have an aliphatic hydrocarbon group, more preferably an aliphatic hydrocarbon group.
• R 8 is preferably selected from a methyl group, an ethyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, an oleyl group, a stearyl group, a phenyl group, a p-octylphenyl group, and a p-nonylphenyl group.
• R 3 is 10 or less, preferably 7 or less, more preferably 4 or less, still more preferably 2 or less, and 1 or more, any of ⁇ 1> to ⁇ 32>
• R 3 is, preferably, a methyl group, an ethyl group, at least one selected from propyl and benzyl group, more preferably a methyl group, according to any one of ⁇ 1> to ⁇ 33> Pigment dispersion for color filters.
• ⁇ 35> (M 1 ) ⁇ is preferably a halide ion, more preferably at least one selected from a chloride ion, a bromide ion and an iodide ion, and more preferably a chloride ion.
• ⁇ 36> (M 2 ) ⁇ is preferably at least one selected from CH 3 SO 4 ⁇ , C 2 H 5 SO 4 — and CH 3 C 6 H 4 SO 3 — , more preferably CH 3 SO 4 - and C 2 H 5 SO 4 - is at least one selected from, more preferably CH 3 SO 4 - a, preferably halide ions, more preferably chloride, bromide
• a pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 35> which is at least one selected from the group consisting of iodide ions and, more preferably, chloride ions.
• the weight average molecular weight of the pigment dispersant is preferably 2,000 or more, more preferably 3,000 or more, further preferably 3,500 or more, and preferably 35,000 or less, more preferably 20
• the pigment dispersant represented by the general formula (I) is preferably a halogenated alkyl ester compound represented by the following general formula (II) and a polyamine compound represented by the following general formula (III):
• the pigment dispersion for color filters according to any one of ⁇ 1> to ⁇ 37>, which is obtained by the reaction of [In the formula (II), R 6 , R 7 , R 8 and a are the same as those described above, and X represents a halogen atom.
• R 1 , R 2 , R 4 , R 5 and (n + m + k) are the same as those described above. ]
• the organic pigment is preferably at least one selected from an azo pigment, a phthalocyanine pigment, a condensed polycyclic pigment, and a lake pigment, preferably a diketopyrrolopyrrole pigment, from ⁇ 1> to ⁇ 38>
• the ether organic solvent is preferably at least one selected from propylene glycol monomethyl ether acetate and diethylene glycol monobutyl ether acetate.
• the content of the organic pigment in the pigment dispersion is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 12% by mass or more, and preferably 30% by mass or less, more preferably
• the mass ratio of the pigment dispersant to the pigment in the pigment dispersion [pigment dispersant / pigment] is preferably 0.2 or more, preferably 0.3 or more, more preferably 0.4 or more, and still more preferably.
• the mass ratio of the pigment dispersant to the pigment in the pigment dispersion [pigment dispersant / pigment] is preferably 1.5 or less, more preferably 1.2 or less, more preferably 0.9 or less, and still more preferably.
• the content of the ether organic solvent in the pigment dispersion is preferably 20% by mass or more, more preferably 40% by mass or more, still more preferably 60% by mass or more, and preferably 95% by mass or less.
• the pigment dispersion for a color filter according to any one of ⁇ 1> to ⁇ 43> preferably 90% by mass or less.
• a coloring composition for a color filter comprising the pigment dispersion according to any one of ⁇ 1> to ⁇ 44> and a binder component.
• a method for producing a pigment dispersion for a color filter comprising the following steps.
• R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group.
• R 5 represents an alkanediyl group having 1 to 18 carbon atoms (where R 5 adjacent to R 1 represents a single bond), and
• R 6 represents an alkanediyl group having 1 to 4 carbon atoms.
• R 7 represents an alkanediyl group having 2 to 4 carbon atoms
• R 8 represents a hydrocarbon group having 1 to 18 carbon atoms
• a represents an average addition mole number, and 1 to 100
• M 1 ) ⁇ and (M 2 ) ⁇ each independently represents an anion
• n, m, and k represent the average number of structural units, (n + m + k) is from 1 to 5, and n is from 1 to 5
• M is 0 or more and 4 or less
• k is 0 or more and 4 or less.
• ⁇ 48> Use of the pigment dispersion according to any one of ⁇ 1> to ⁇ 44> for producing a color filter.
• ⁇ 49> Use of the colored composition according to ⁇ 45> or ⁇ 46> for producing a color filter.
• ⁇ 50> A color filter produced using the pigment dispersion according to any one of ⁇ 1> to ⁇ 44>.
• ⁇ 51> A method for producing a color filter using the colored composition according to ⁇ 45> or ⁇ 46>.
• X in the notation “polyalkylene glycol (X)” means the average number of moles of alkylene oxide added to the polyalkylene glycol.
• the average addition mole number of propylene oxide (hereinafter also referred to as “PO”) and ethylene oxide (hereinafter also referred to as “EO”) in the alkoxypolyalkylene glycol the weight average molecular weight, the solid content, and the reaction rate in the production example of the pigment dispersant.
• PO propylene oxide
• EO ethylene oxide
• the weight average molecular weight was measured by either ⁇ Condition 1> or ⁇ Condition 2> below.
• the measurement sample was prepared as follows.
• the amount of the solid content of the solution containing the compound obtained in the below-mentioned production example is 0.05 g in a glass bottle ("Screw tube No. 5" manufactured by Maruem Co., Ltd.), and the total amount is obtained by adding the following eluent. 10 g and sealed. Subsequently, the glass bottle was stirred at 2500 rpm for 1 minute using a test tube mixer (“Minishaker MS1” manufactured by IKA), and 100 ⁇ L of the resulting solution was used as a measurement sample.
• Solid content (mass%) [(mass after drying g) ⁇ (Petri dish + glass rod + mass g of dried anhydrous sodium sulfate)] / (mass g of sample) ⁇ 100
• Reaction rate measurement (chlorine ion content ratio standard) Since the chlorine of the alkoxypolyalkylene glycol monochloroacetate is converted into a chlorine ion by the reaction, the reaction rate based on the ratio of the chlorine ion amount was calculated from the following equation.
• Reaction rate (%) [chlorine ion amount (mass%)] / [total chlorine content (mass%)] ⁇ 100
• the chlorine ion content was determined by the Volhard method, and the total chlorine content was determined by the Volhard method after decomposition with sodium butyrate.
• Ammonium reduction standard Since the polyamine becomes a quaternary salt by the reaction and the amine value decreases, the reaction rate based on the amount of amine decrease was calculated from the following equation.
• Reaction rate (%) [(amine value before reaction mgKOH / g) ⁇ (amine value after reaction mgKOH / g)] / (amine value before reaction mgKOH / g) ⁇ 100 The amine value was measured by “tertiary amine value” of ASTM D2073-66.
• n, m, and k were determined from the amine value after the reaction and the amounts of (M 1 ) ⁇ and (M 2 ) ⁇ described later.
• the ratio of n KOH , m KOH and k KOH, which will be described later, is the ratio of n, m and k, and n + m + k is equal to the average number of amine moles (n + m + k) of the polyamine compound used for the synthesis of the pigment dispersant in the production example.
• n, m, and k were respectively calculated.
• n KOH and k KOH are numerical values obtained by converting the number of quaternary ammonium groups contained in the structural units represented by n and k into amine values.
• N KOH was calculated from the following equation.
• n KOH [(M 1) - the amount (wt%)] / (100 ⁇ [ (M 1) - molecular weight]) ⁇ 56 ⁇ 1000
• m KOH was defined as the amine value (mg KOH / g) after the reaction.
• K KOH was calculated from the following equation.
• k KOH ⁇ [(M 2 ) - the amount (wt%)] / (100 ⁇ [ (M 2) - molecular weight of]) ⁇ ⁇ 56 ⁇ 1000
• Cl ⁇ a value obtained by quantifying the chlorine concentration relative to the solid content in the sample by the Volhard method was used.
• the amount of (M 1 ) ⁇ and (M 2 ) ⁇ was measured by the following method.
• 0.1 g of the solution containing the pigment dispersant obtained in the production example described later was diluted 1000 to 5000 times with ultrapure water to obtain a solution having a known pigment dispersant concentration, and 25 ⁇ L thereof was used as a measurement sample. .
• the sample to be measured was ion chromatography (apparatus: “Dionex ICS-2100” manufactured by Thermo Scientific, suppressor: ASRS-300, detector: electrical conductivity detector (attached to the apparatus), detector temperature: 35 ° C., Column: “Ion Pac AS11-HC + Ion Pac AG11-HC” manufactured by Nippon Dionex Co., Ltd., flow rate: 1.5 mL / min, column temperature: 35 ° C., eluent: potassium hydroxide solution].
• the eluent concentration was 10 to 40 mmol / L (25 min) linear gradient elution.
• a sodium salt of (M 1 ) ⁇ or (M 2 ) ⁇ was used.
• the cumulant average particle size obtained by cumulant analysis was defined as the average particle size of the pigment dispersion.
• the refractive index of BCA was 1.426 and its viscosity was 3.1 mPa ⁇ s.
• the cumulant average was measured by the method described in the above “(9) Measurement of average particle diameter of pigment dispersion”. The particle size was measured.
• the visual evaluation of redispersibility was performed according to the following criteria. A: The coating film does not remain on the glass plate, and all the peeled material of the coating film is dissolved or dispersed. B: Although the coating film does not remain on the glass plate, a part of the exfoliation of the coating film is dissolved or dispersed and becomes a part of a precipitate.
• C A part of the coating film remains on the glass plate, and the peeled material of the coating film partially dissolves or disperses, resulting in a partial precipitate.
• D Part of the coating film remains on the glass plate, and all the peeled material of the coating film becomes a precipitate.
• Synthesis Example 6 [Synthesis of Methoxypolypropylene Glycol (29) Polyethylene Glycol (15) Monochloroacetate] 1550 g of methoxypolypropylene glycol (29) polyethylene glycol (15) obtained in Synthesis Example 1 and monochloroacetic acid (Wako Pure Chemical Industries, Ltd.) were added to a 3 liter four-necked flask equipped with a stirrer, thermometer, nitrogen blowing tube and cooling tube.
• a special grade reagent (manufactured by Co., Ltd.) 83.3 g and 11.1 g of p-toluenesulfonic acid monohydrate (manufactured by Kishida Chemical Co., Ltd., special grade reagent) were charged, and nitrogen substitution was performed while stirring. After raising the temperature to 140 ° C., while blowing nitrogen, using a vacuum pump (“BSW-50” manufactured by Sato Vacuum Machine Industry Co., Ltd.) connected to a cooling pipe, reducing pressure ( ⁇ 0.1 MPa) for 16 hours Reacted.
• a vacuum pump (“BSW-50” manufactured by Sato Vacuum Machine Industry Co., Ltd.) connected to a cooling pipe, reducing pressure ( ⁇ 0.1 MPa) for 16 hours Reacted.
• Synthesis Example 7 [Synthesis of Lauroxy Polypropylene Glycol (29) Polyethylene Glycol (15) Monochloroacetate] 1550 g of methoxypolypropylene glycol (29) polyethylene glycol (15) to 653 g of lauroxypolypropylene glycol (29) polyethylene glycol (15) obtained in Synthesis Example 2, 83.3 g of monochloroacetic acid to 35.1 g, and p-toluenesulfone Lauroxypolypropylene glycol (29) polyethylene in the same manner as in Synthesis Example 3, except that 11.1 g of acid monohydrate was changed to 3.5 g and 50.6 g of anhydrous sodium carbonate were changed to 26.8 g. Glycol (15) monochloroacetate was obtained.
• Synthesis Example 8 [Synthesis of Phenoxy Polypropylene Glycol (29) Polyethylene Glycol (15) Monochloroacetate] 1550 g of methoxypolypropylene glycol (29) polyethylene glycol (15) is added to 653 g of the phenoxypolypropylene glycol (29) polyethylene glycol (15) obtained in Synthesis Example 3, 83.3 g of monochloroacetic acid is changed to 36.1 g, and p-toluenesulfonic acid -Phenoxypolypropylene glycol (29) polyethylene glycol (monohydrate in the same manner as in Synthesis Example 6 except that 11.1 g of monohydrate was changed to 3.6 g and 50.6 g of anhydrous sodium carbonate was changed to 28.8 g. 15) Monochloroacetate was obtained.
• Synthesis Example 9 [Synthesis of Lauroxy Polypropylene Glycol (29) Monochloroacetate] Methoxypolypropylene glycol (29) Polyethylene glycol (15) 1550 g of lauroxy polypropylene glycol (29) obtained in Synthesis Example 4 458 g, monochloroacetic acid 83.3 g to 35.7 g, p-toluenesulfonic acid monohydrate Lauroxy polypropylene glycol (29) monochloroacetate was obtained in the same manner as in Synthesis Example 6 except that 11.1 g was changed to 2.8 g and anhydrous sodium carbonate 50.6 g was changed to 47.0 g.
• Synthesis Example 10 [Synthesis of Lauroxy Polypropylene Glycol (15) Polyethylene Glycol (29) Monochloroacetate] 1550 g of methoxypolypropylene glycol (29) polyethylene glycol (15) 450 g of lauroxy polypropylene glycol (15) polyethylene glycol (29) obtained in Synthesis Example 5, 83.3 g of monochloroacetic acid to 28.5 g, and p-toluenesulfonic acid -Lauroxypolypropylene glycol (15) polyethylene glycol in the same manner as in Synthesis Example 6 except that 11.1 g of monohydrate was changed to 2.7 g and 50.6 g of anhydrous sodium carbonate was changed to 49.5 g. (29) Monochloroacetate was obtained.
• Synthesis Example 11 [Synthesis of poly tertiary amine glycol (average number of amine moles: 3.7)]
• a 1 L flask equipped with a condenser and a separator for separating reaction water was charged with 600 g of 1,6-hexanediol and 12 g of a Cu—Ni catalyst (“MX-2141” manufactured by Kao Corporation). While stirring, the inside of the system was replaced with nitrogen, and the temperature was raised. Simultaneously with the start of temperature increase, hydrogen gas was blown into the reaction system at a flow rate of 30 L / hr, and the temperature was increased to 185 ° C. over about 40 minutes.
• the reaction was allowed to proceed for 20 hours while stirring at 80 ° C. 120 g of propylene glycol monomethyl ether acetate (PGMEA) was added, stirred for 1 hour, cooled, and pigment dispersant (1) (methoxypolypropylene glycol (29) polyethylene glycol (15) N, N, N ′ by monochloroacetate, N′-tetramethylhexanediamine quaternized product) was obtained.
• the solid content of the solution was 43.5% by mass, and the weight average molecular weight was 3800 (measured value according to ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 94 mol%, and the reaction rate obtained from the amine reduction amount was 96 mol%.
• n 1.9, m was 0.1, and k was 0.0.
• the signals derived from the methyl group and methylene group bonded to N of N, N, N ′, N′-tetramethylhexanediamine were changed from 2.2 ppm to 3.1 and 3.9 ppm by reaction, respectively.
• the signals derived from the methylene group one further away from N and the methylene group two away from N migrated from 1.5 and 1.4 ppm to 2.0 and 1.5 ppm, respectively.
• the solid content of the solution was 41.5% by mass, and the weight average molecular weight was 2500 (measured value under ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 94 mol%, and the reaction rate obtained from the amine reduction amount was 96 mol%.
• n was 1.0, m was 0.0, and k was 0.0.
• the signals derived from the methyl group and methylene group bonded to N of N, N-dimethylaminohexanol were separated from 2.2 ppm to 3.5 and 3.6 ppm, respectively, and one more from N due to the reaction.
• the signals derived from the methylene group and the two methylene groups separated from each other shifted from 1.5 and 1.4 ppm to 2.0 and 1.5 ppm, respectively. Further, the signal derived from the methylene group to which chlorine of methoxypolypropylene glycol (29) polyethylene glycol (15) monochloroacetate was bonded shifted from 4.1 ppm to 4.9 ppm by the reaction.
• the structure of the pigment dispersant (2) obtained in this production example is shown in Table 1 by applying it to the general formula (I) in this specification.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 100 mol%, and the reaction rate obtained from the amine reduction amount was 98 mol%.
• n was 3.6, m was 0.1, and k was 0.0.
• signals derived from methyl group and methylene group bonded to N of poly tertiary amine glycol were 2.2, 2.3 ppm to 3.1, respectively, depending on the reaction.
• signals derived from a methylene group one further away from N and a methylene group two further away from N shifted from 1.5 and 1.3 ppm to 1.9 and 1.5 ppm, respectively.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 97 mol%, and the reaction rate obtained from the amine reduction amount was 97 mol%.
• n was 4.9, m was 0.1, and k was 0.0.
• the signals derived from the methyl group and methylene group bonded to N of poly tertiary amine glycol (average amine mole number: 5.0) were 2.2, 2.3 ppm to 3.5, respectively, depending on the reaction.
• signals derived from methylene groups one more and two methylene groups further away from N migrated from 1.5, 1.3 ppm to 1.9, 1.5 ppm, respectively.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 97 mol%, and the reaction rate obtained from the amine reduction amount was 100 mol%.
• n 2.0, m was 0.0, and k was 0.0.
• the N, N, N ′, N′-tetramethylnonanediamine was synthesized by the method described in “0021” of JP-A-7-90040. As a result of NMR measurement, the signals derived from the methyl group and methylene group bonded to N of N, N, N ′, N′-tetramethylnonanediamine were changed from 2.2 ppm to 3.0 and 3.9 ppm by reaction, respectively.
• the pigment dispersant (7) (methoxypolypropylene glycol (29) polyethylene glycol (15) N by monochloroacetate was used. , N, N ′, N′-tetramethylpropanediamine quaternized product) was obtained.
• the solid content of the solution was 42.1% by mass, and the weight average molecular weight was 3800 (measured value according to ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 94 mol%, and the reaction rate obtained from the amine reduction amount was 94 mol%.
• n was 1.9, m was 0.1, and k was 0.0.
• N, N, N ′, N′-tetramethylpropanediamine quaternized with pigment dispersant (8) lauroxy polypropylene glycol (29) polyethylene glycol (15) monochloroacetate ) PGMEA solution was obtained.
• the solid content of the solution was 39.4% by mass, and the weight average molecular weight was 4000 (measured value according to ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 93 mol%, and the reaction rate obtained from the amine reduction amount was 99 mol%.
• n 2.0, m was 0.0, and k was 0.0.
• signals derived from the methyl group and methylene group bonded to N of N, N, N ′, N′-tetramethylpropanediamine were 2.2, 2.3 ppm to 3.0, respectively, depending on the reaction.
• the signal derived from the methylene group one further away from N shifted from 1.6 ppm to 2.8 ppm.
• the signal derived from the methylene group to which chlorine of lauroxypolypropylene glycol (29) polyethylene glycol (15) monochloroacetate was bonded shifted from 4.1 ppm to 4.9 ppm by the reaction.
• the structure of the pigment dispersant (8) obtained in this production example is shown in Table 1 by applying it to the general formula (I) in this specification.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 95 mol%, and the reaction rate obtained from the amine reduction amount was 97 mol%.
• n was 5.8, m was 0.2, and k was 0.0.
• signals derived from a methyl group and a methylene group bonded to N of poly tertiary amine glycol (average amine mole number: 6.0) were 2.2, 2.3 ppm to 3.5, respectively, depending on the reaction.
• signals derived from methylene groups one more and two methylene groups further away from N migrated from 1.5, 1.3 ppm to 1.9, 1.5 ppm, respectively.
• PGMEA solution of pentamethyldiethylenetriamine quaternized product by pigment dispersant (10) (lauroxy polypropylene glycol (29) polyethylene glycol (15) monochloroacetate was obtained.
• the solid content of the solution was 40.8% by mass,
• the weight average molecular weight was 3800 (measured by ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 92 mol%, and the reaction rate obtained from the amine reduction amount was 66 mol%.
• n was 1.8, m was 1.2, and k was 0.0.
• a PGMEA solution of pentamethyldipropylenetriamine quaternized product with pigment dispersant (11) (lauroxy polypropylene glycol (29) polyethylene glycol (15) monochloroacetate was obtained.
• the solid content of the solution was 40.6% by mass.
• the weight average molecular weight was 4100 (measured value according to ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 93 mol%, and the reaction rate obtained from the amine reduction amount was 66 mol%.
• n was 1.9, m was 1.1, and k was 0.0.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 95 mol%, and the reaction rate obtained from the amine reduction amount was 33 mol%.
• n was 0.9, m was 2.1, and k was 0.0.
• the signals derived from the methyl group and methylene group bonded to N of pentamethyldipropylenetriamine were changed from 2.2, 2.3 ppm to 3.6, and 3.7 ppm, respectively, from N to 1 by reaction.
• the signal derived from a distant methylene group partially shifted from 1.6 ppm to 2.1 ppm.
• pigment dispersant (16) lauroxy polypropylene glycol (29) polyethylene glycol (15) monochloroacetate and pentamethyldipropylene triamine quaternized product with dimethyl sulfate.
• the solid content of the solution was 38.7% by mass, and the weight average molecular weight was 4100 (measured value according to ⁇ Condition 1>).
• the reaction rate determined from the amount of amine reduction was 99 mol%.
• n was 2.0, m was 0.0, and k was 1.0.
• Pigment Dispersant (14) (Lauroxy Polypropylene Glycol (29) Polyethylene Glycol (15) Monochloroacetate and Pentamethyldipropylene Triamine Quaternized with Dimethyl Sulfate)]
• a pigment dispersant (14) was prepared in the same manner as in Production Example 13, except that the PGMEA solution obtained in Production Example 11 was replaced with the PGMEA solution obtained in Production Example 12 by replacing 1.6 g of dimethyl sulfate with 3.2 g. ) (Lauroxy polypropylene glycol (29) Polyethylene glycol (15) Monochloroacetate and pentamethyldipropylene triamine quaternized product with dimethyl sulfate) was obtained.
• the solid content of the solution was 39.5% by mass, and the weight average molecular weight was 2200 (measured value under ⁇ Condition 1>).
• the reaction rate determined from the amount of amine reduction was 99 mol%.
• n was 1.0, m was 0.0, and k was 2.0.
• the signals derived from the methyl group and methylene group bonded to N of pentamethyldipropylenetriamine were changed from 2.2, 2.3 ppm to 3.6, 3.7 ppm, respectively, by reaction, and further from N.
• a signal derived from a methylene group that was one distance away shifted from 1.6 ppm to 2.1 ppm.
• the pigment dispersant (phenoxypolypropylene glycol (29) polyethylene glycol (15) N, N, N ′, N′-tetramethylpropanediamine quaternized product with monochloroacetate) was prepared in the same manner as in Production Example 1.
• a PGMEA solution was obtained.
• the solid content of the solution was 40.5% by mass, and the weight average molecular weight was 3900 (measured value according to ⁇ Condition 1>).
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 94 mol%, and the reaction rate obtained from the amine reduction amount was 99 mol%.
• n 2.0, m was 0.0, and k was 0.0.
• signals derived from the methyl group and methylene group bonded to N of N, N, N ′, N′-tetramethylpropanediamine were 2.2, 2.3 ppm to 3.0, respectively, depending on the reaction.
• the signal derived from the methylene group one further away from N shifted from 1.6 ppm to 2.8 ppm.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 93 mol%, and the reaction rate obtained from the amine reduction amount was 90 mol%.
• n was 1.8, m was 0.2, and k was 0.0.
• signals derived from the methyl group and methylene group bonded to N of N, N, N ′, N′-tetramethylpropanediamine were 2.2, 2.3 ppm to 3.0, respectively, depending on the reaction.
• the signal derived from the methylene group one further away from N shifted from 1.6 ppm to 2.8 ppm.
• the reaction rate obtained from the ratio of the chlorine ion content to the total chlorine content was 94 mol%, and the reaction rate obtained from the amine reduction amount was 93 mol%.
• n was 1.9, m was 0.1, and k was 0.0.
• signals derived from the methyl group and methylene group bonded to N of N, N, N ′, N′-tetramethylpropanediamine were 2.2, 2.3 ppm to 3.0, respectively, depending on the reaction.
• the signal derived from the methylene group one further away from N shifted from 1.6 ppm to 2.8 ppm.
• Pigment Dispersant (18) Lauroxy Polypropylene Glycol (29) Polyethylene Glycol (15) Monochloroacetate and Pentamethyldipropylene Triamine Quaternized with Diethyl Sulfate
• Pigment dispersant (18) lauroxypolypropylene glycol (29) polyethylene glycol (15) monochloroacetate, and sulfuric acid were produced in the same manner as in Production Example 13 except that 1.6 g of dimethyl sulfate was replaced with 2.0 g of diethyl sulfate.
• a PGMEA solution of pentamethyldipropylenetriamine quaternized product with diethyl) was obtained.
• the solid content of the solution was 38.7% by mass, and the weight average molecular weight was 4100 (measured value according to ⁇ Condition 1>).
• the structure of the pigment dispersant (18) obtained in this production example is shown in Table 1 by applying it to the general formula (I) in this specification. n was 2.0, m was 0.0, and k was 1.0.
• a PGMEA solution of pentamethyldipropylenetriamine quaternized product with acetate and methyl p-toluenesulfonate was obtained.
• the solid content of the solution was 38.9% by mass, and the weight average molecular weight was 4100 (measured value according to ⁇ Condition 1>).
• the structure of the pigment dispersant (19) obtained in this Production Example is shown in Table 1 by applying it to the general formula (I) in this specification. n was 2.0, m was 0.0, and k was 1.0.
• Example 1 Preparation of pigment dispersion (1)
• Diketopyrrolopyrrole pigment (CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.) 15 g, PGMEA 121.2 g, Pigment dispersant (1) solution obtained in Production Example 1 13.8 g (solid content 6.0 g), 300 g of zirconia beads having a particle size of 0.3 mm are placed in a 500 mL plastic container, and dispersion (preliminary dispersion) with a disperser (“Paint Shaker” manufactured by Asada Tekko Co., Ltd.) is performed for 3 hours. And the zirconia beads were removed by filtration.
• Pigment dispersion (1) 7.5 parts by mass, benzyl methacrylate / methacrylic acid copolymer (alkali-soluble resin, molar ratio: 70/30, weight average molecular weight: 14000, PGMEA solution having a solid content of 50% by mass) 0.85 Parts by mass, dipentaerythritol hexaacrylate (polyfunctional monomer: “DPHA” manufactured by Nippon Kayaku Co., Ltd.) 0.30 parts by mass, 2-methyl-4 ′-(methylthio) -2-morpholinopropiophenone (photopolymerization) Initiator: Wako Pure Chemical Industries, Ltd.) 0.23 parts by mass and 1.13 parts by mass of PGMEA were mixed until uniform to obtain a colored composition (1).
• benzyl methacrylate / methacrylic acid copolymer alkali-soluble resin, molar ratio: 70/30, weight average molecular weight: 14000
• Examples 2 to 8 and Comparative Example 1 (Preparation of pigment dispersions (2) to (8) and (51) and colored compositions (2) to (8) and (51))
• the pigment dispersant (1) is replaced with the pigment dispersants (2) to (9), respectively, so that the solid content of each pigment dispersant solution is 6.0 g, and the total amount of each pigment dispersant solution and PGMEA is Pigment dispersions (2) to (8) and (51) and colored compositions (2) to (8) and (51) were prepared in the same manner as in Example 1 except that the amount of PGMEA was adjusted to 135 g. )
• Example 9 (Preparation of pigment dispersion (9)) Example 1 except that the amount of PGMEA was adjusted so that the solid content of the pigment dispersant (1) solution was 10.5 g and the total amount of the pigment dispersant (1) solution and PGMEA was 135 g. In the same manner as in Preparation of pigment dispersion (1), pigment dispersion (9) was obtained.
• Pigment dispersion (9) 7.5 parts by mass, benzyl methacrylate / methacrylic acid copolymer (alkali-soluble resin, molar ratio: 70/30, weight average molecular weight: 14000, PGMEA solution having a solid content of 50% by mass) 0.64 Parts by mass, dipentaerythritol hexaacrylate (polyfunctional monomer: “DPHA” manufactured by Nippon Kayaku Co., Ltd.) 0.23 parts by mass, 2-methyl-4 ′-(methylthio) -2-morpholinopropiophenone (photopolymerization) Initiator: Wako Pure Chemical Industries, Ltd.) 0.17 parts by mass and 1.45 parts by mass of PGMEA were mixed until uniform to obtain a colored composition (9).
• benzyl methacrylate / methacrylic acid copolymer alkali-soluble resin, molar ratio: 70/30, weight average molecular weight: 14000
• Example 10 (Preparation of pigment dispersion (10)) Diketopyrrolopyrrole pigment (CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.) The solid content of the pigment dispersant (1) solution is 9. The amount of PGMEA was adjusted so that the total amount of the pigment dispersant (1) and PGMEA was 127.5 g, and other than that was the same as Example 1 (Preparation of pigment dispersion (1)). Thus, a pigment dispersion (10) was obtained.
• Diketopyrrolopyrrole pigment CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.
• the solid content of the pigment dispersant (1) solution is 9.
• the amount of PGMEA was adjusted so that the total amount of the pigment dispersant (1) and PGMEA was 127.5 g, and other than that was the same as Example 1 (Preparation of pigment dispersion (1)).
• Example 11 (Preparation of pigment dispersion (11) and coloring composition (11)) Diketopyrrolopyrrole pigment (CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.) and anthraquinone pigment (CI Pigment Red 177 manufactured by Dainichi Seika Kogyo Co., Ltd.) Chromofine Red 6128EC "), except that the main dispersion time was changed from 24 hours to 9 hours, respectively, to obtain a pigment dispersion (11) and a colored composition (11) in the same manner as in Example 1. .
• Diketopyrrolopyrrole pigment CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.
• anthraquinone pigment CI Pigment Red 177 manufactured by Dainichi Seika Kogyo Co., Ltd.
• Chromofine Red 6128EC Chromofine Red 6128
• Example 12 Preparation of pigment dispersion (12) and coloring composition (12)
• Diketopyrrolopyrrole pigment CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.
• phthalocyanine pigment CI Pigment Blue 15 manufactured by Dainichi Seika Kogyo Co., Ltd.: 6 “A454”
• the main dispersion time was changed from 24 hours to 4.5 hours, respectively, to obtain a pigment dispersion (12) and a colored composition (12) in the same manner as in Example 1. It was.
• Example 13 (Preparation of pigment dispersion (13) and colored composition (13)) A pigment dispersion (13) and a colored composition (13) were obtained in the same manner as in Example 1 except that 121.2 g of PGMEA was replaced with 121.2 g of diethylene glycol monobutyl ether acetate (BCA).
• BCA diethylene glycol monobutyl ether acetate
• Example 14 (Preparation of colored composition (14)) Pigment Dispersion (1) 7.5 parts by mass is 4.62 parts by mass, benzyl methacrylate / methacrylic acid copolymer (alkali-soluble resin, molar ratio: 70/30, weight average molecular weight: 14000, solid content 50% by mass PGMEA solution) 0.85 parts by mass to 1.20 parts by mass, dipentaerythritol hexaacrylate (polyfunctional monomer: “DPHA” manufactured by Nippon Kayaku Co., Ltd.) 0.30 parts by mass to 0.43 parts by mass 2-methyl-4 ′-(methylthio) -2-morpholinopropiophenone (photopolymerization initiator: manufactured by Wako Pure Chemical Industries, Ltd.) 0.23 parts by mass to 0.32 parts by mass, PGMEA 1.13 A colored composition (14) was obtained in the same manner as in Example 1 (Preparation of colored composition (1)) except that the mass part was changed to 3.43 parts by mass.
• Comparative Example 2 (Preparation of pigment dispersion (52))
• the solvent of the commercially available dispersant “Solsperse 76500 (solid content 50% by mass, manufactured by Lubrizol)” was removed by an evaporator, and the obtained solid content was used as a pigment dispersant (52).
• the pigment dispersant (52) was dissolved in PGMEA to obtain a pigment dispersant (52) solution (40 mass% PGMEA solution with the solid content).
• Pigment dispersant (1) solution 13.8 g (solid content 6.0 g) is replaced by pigment dispersant (52) solution 15.0 g (solid content 6.0 g), and the total amount of pigment dispersant (52) solution and PGMEA
• the amount of PGMEA was adjusted so as to be 135 g, and a pigment dispersion (52) and a colored composition (52) were obtained in the same manner as in Example 1 except that.
• Comparative Example 3 (Preparation of pigment dispersion (53) and colored composition (53)) Replace the pigment dispersant (1) with 6 g of the commercially available dispersant (53) “Azisper PB821 (Ajinomoto Co., Inc.)” and adjust the amount of PGMEA so that the total amount of “Azisper PB821” and PGMEA is 135 g. Other than that was carried out similarly to Example 1, and obtained the pigment dispersion (53) and the coloring composition (53).
• Comparative Example 4 Preparation of pigment dispersion (54) and coloring composition (54)
• Diketopyrrolopyrrole pigment CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.
• anthraquinone pigment CI Pigment Red 177 manufactured by Dainichi Seika Kogyo Co., Ltd.
• a dispersion (54) and a colored composition (54) were obtained in the same manner as in Comparative Example 2, except that the main dispersion was changed from 24 hours to 9 hours.
• Comparative Example 5 (Preparation of pigment dispersion (55) and coloring composition (55)) Diketopyrrolopyrrole pigment (CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.) and phthalocyanine pigment (CI Pigment Blue 15 manufactured by Dainichi Seika Kogyo Co., Ltd.): 6 “A454”), except that this dispersion was changed from 24 hours to 4.5 hours, respectively, to obtain a comparative pigment dispersion (55) and a colored composition (55) in the same manner as in Comparative Example 2. .
• Diketopyrrolopyrrole pigment CI Pigment Red 254 “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co., Ltd.
• phthalocyanine pigment CI Pigment Blue 15 manufactured by Dainichi Seika Kogyo Co., Ltd.
• Examples 15-24 Preparation of pigment dispersions (14) to (23) and colored compositions (15) to (24) and (51)
• the pigment dispersant (1) is replaced with pigment dispersants (10) to (19), respectively, so that the solid content of each pigment dispersant solution is 6.0 g, and the total amount of each pigment dispersant solution and PGMEA is Pigment dispersions (14) to (23) and colored compositions (15) to (24) were obtained in the same manner as in Example 1 except that the amount of PGMEA was adjusted to 135 g.
• the pigment dispersions and coloring compositions of Examples 1 to 24 have a smaller average particle diameter and lower viscosity than the pigment dispersions and coloring compositions of Comparative Examples 1 to 5, and after storage. Has a low viscosity and good redispersibility. Therefore, it can be seen that the pigment dispersion of the present invention is excellent in dispersibility, storage stability and solvent resolubility.

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