WO2007013475A1 - Procédé de production d'une composition contenant des particules organiques dispersées - Google Patents

Procédé de production d'une composition contenant des particules organiques dispersées Download PDF

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Publication number
WO2007013475A1
WO2007013475A1 PCT/JP2006/314700 JP2006314700W WO2007013475A1 WO 2007013475 A1 WO2007013475 A1 WO 2007013475A1 JP 2006314700 W JP2006314700 W JP 2006314700W WO 2007013475 A1 WO2007013475 A1 WO 2007013475A1
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group
organic
pigment
solvent
meth
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PCT/JP2006/314700
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English (en)
Japanese (ja)
Inventor
Naoya Shibata
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Fujifilm Corporation
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Priority to JP2007528487A priority Critical patent/JPWO2007013475A1/ja
Publication of WO2007013475A1 publication Critical patent/WO2007013475A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0005—Coated particulate pigments or dyes the pigments being nanoparticles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • 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
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors

Definitions

  • the present invention relates to a method for producing an organic particle dispersion composition by efficiently concentrating organic particles produced by an organic particle precipitation method. More specifically, the desalted organic particle dispersion composition is described above. It relates to a manufacturing method. Furthermore, in the production method described above, a method for producing an organic particle dispersion composition that suppresses changes in the particle size and monodispersity of the organic particles in the concentration step and can be easily redispersed even when aggregated by concentration. About.
  • nanometer-sized fine particles is different from that of larger nano particles and smaller molecules and atoms, and is located in the middle. Therefore, it has been pointed out that new characteristics that could not be predicted in the past can be extracted.
  • nanometer (nm) scale microcrystals exhibit various interesting properties such as catalytic effects based on unique surface structures, photophysical properties due to size effects, and nonlinear optical properties. However, if this monodispersity can be increased, the characteristics can be stabilized.
  • the potential of such nanoparticles is expected in various fields, and research is being actively conducted in a wide range of fields such as biochemistry, new materials, electronic devices, light-emitting display devices, printing, and medicine.
  • organic nanoparticles composed of organic compounds have a high potential as functional materials because the organic compounds themselves are diverse.
  • greater electrical insulation can be expected by combining finely divided substances such as polyimide that are excellent in electrical insulation.
  • organic pigments include, for example, paints, printing inks, electrophotographic toners, inkjet inks, color filters, and the like. It is now an important material that is indispensable in daily life. Among these, high performance is required, and pigments for inkjet ink and pigments for color filters are particularly important for practical use.
  • a gas phase method (a method in which a sample is sublimated in an inert gas atmosphere and particles are collected on a substrate), a liquid phase method (for example, a sample dissolved in a good solvent is stirred) (Reprecipitation method to obtain fine particles by injecting into a poor solvent with controlled conditions and temperature), laser ablation method (a method to make particles fine by irradiating a sample dispersed in a solution with a laser) Etc. are being studied.
  • laser ablation method a method to make particles fine by irradiating a sample dispersed in a solution with a laser
  • the reprecipitation method is a method for producing organic particles excellent in simplicity and productivity, but is not yet sufficient as a method for producing particles with high industrial utilization.
  • sufficient research has not been conducted on how to separate and recover organic particles prepared by the reprecipitation method.
  • the prepared organic particles are obtained dispersed in a dilute solvent.
  • unnecessary salt is contained in a large amount with respect to organic particles, and for example, it may become a liquid crystal contaminant in color filter applications. Therefore, the ability to remove unnecessary salts and separate and recover organic particles becomes a problem. Even if the desired particles can be prepared in the dispersion, In the collecting process, the particle size is changed, the monodispersity of the particles is deteriorated, and it is impossible to put it to practical use if the collection requires a large cost.
  • Patent Document 4 discloses a method of adding an evaporation promoting liquid to a particle-containing aqueous dispersion and concentrating it by distillation.
  • this method is applied to organic particle-containing aqueous dispersions prepared by the reprecipitation method, when the boiling point of the good solvent of the organic material is higher than that of water, only the water evaporates. There is a concern that the concentration increases and the particle size of the organic particles increases during concentration.
  • Patent Document 5 discloses a method in which an ionic liquid that does not substantially dissolve in the dispersion medium is added to a dispersion containing fine particles, and the fine particles are concentrated in the ionic liquid. However, this method alone cannot sufficiently concentrate the organic particle dispersion to the desired concentration.
  • Patent Document 6 discloses a method of obtaining fine organic particles by dissolving an organic pigment and a dispersant together and precipitating the particles in a poor solvent. In this method, if the organic particles are then agglomerated by adding acid, and concentration and desalting are performed, the change in particle size due to redispersion is relatively small. However, the redispersion liquid obtained by this method has a large amount of particles contained therein, and when applied to, for example, a CCD color filter, the density of a specific pixel is lowered.
  • Patent Document 1 Japanese Translation of Special Publication 2002-092700
  • Patent Document 2 JP-A-6-79168
  • Patent Document 3 Japanese Patent Application Laid-Open No. 2004-91560
  • Patent Document 4 Japanese Patent Application Laid-Open No. 2004-181312
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2004-292632
  • Patent Document 6 Japanese Unexamined Patent Application Publication No. 2004-43776
  • An object of the present invention is to provide a method for producing an organic particle dispersion composition by efficiently concentrating organic particles produced by an organic particle precipitation method, and particularly desalting to provide an organic particle dispersion composition. It is an object to provide a manufacturing method for obtaining.
  • a method for producing an organic particle dispersion composition that suppresses changes in the particle size and monodispersity of organic particles in the concentration step and can be easily redispersed even when aggregated by concentration is provided. Is an issue. According to the present invention, the following means are provided:
  • R 1 represents a (m + n) -valent linking group
  • R 2 represents a single bond or a divalent linking group
  • a 1 is an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, or an isocyanate group.
  • a monovalent organic group having a group selected from the group consisting of a hydroxyl group, or a monovalent organic group which may have a substituent, or an organic dye structure or a heterocyclic ring.
  • n A 1 s may be the same or different.
  • m represents a number from 1 to 8
  • n represents a number from 2 to 9
  • P 1 represents a polymer skeleton.
  • the polymer compound represented by the general formula (1) is formed when organic nanoparticles are formed, extracted or concentrated, and when aggregated organic particles are dispersed after concentration.
  • An inkjet ink for a color filter characterized in that an inkjet ink for a color filter is prepared from the organic nanoparticle dispersion composition produced by the production method according to any one of (1) to (10). Production method.
  • a photosensitive transfer material wherein a photosensitive resin layer containing at least the colored photosensitive resin composition according to (12) is provided on a temporary support.
  • a light-shielding partition is formed on the substrate, and a plurality of recesses separated by the partition are provided, and R (red) ink, G (green) ink, and B (blue) ink are formed by an inkjet method.
  • a method of manufacturing a color filter in which each of the recesses is sprayed and deposited to form a colored resin layer of each color in each recess, and at least the R ink, the G ink, and the B ink A color filter characterized by using an inkjet ink obtained by the production method described in (11) as one type.
  • a liquid crystal display device comprising the color filter according to (14) or (15).
  • a CCD device comprising the color filter according to (14) or (15).
  • organic particles are produced by an organic particle precipitation method, and the dispersion solvent and unnecessary salts in the dispersion are removed to make the organic particles efficient. It can be well concentrated to the desired concentration.
  • the method for producing an organic nanoparticle dispersion composition of the present invention when producing organic particles by the organic particle precipitation method, when increasing the amount of good solvent relative to the poor solvent, or when increasing the production scale. However, it can be concentrated and desalted without substantially increasing the particle size and the monodispersity, and the aggregated organic particles can be easily redispersed with high efficiency. Organic particles can be produced.
  • the concentrated organic particle paste produced by the method for producing an organic particle dispersion composition of the present invention and the organic particles obtained therefrom are suitable inkjet inks or raw material fine particles thereof, or color filter coating liquids or fine raw material particles thereof. Is available as In addition, the color filter, the liquid crystal display device, and the CCD device of the present invention exhibit excellent effects when exhibiting high display characteristics.
  • FIG. 1-1 is a cross-sectional view schematically showing a preferred embodiment of a production apparatus used in the method for producing an organic particle dispersion composition of the present invention.
  • FIG. 1-2 is an enlarged partial cross-sectional view schematically showing a mixing chamber in a partial cross section as one embodiment of the manufacturing apparatus of FIG.
  • FIG. 1-3 is an enlarged partial cross-sectional view schematically showing a mixing chamber in a partial cross section as another embodiment of the manufacturing apparatus of FIG.
  • FIG. 2 is a cross-sectional view schematically showing another preferred embodiment of a production apparatus used in the method for producing an organic particle dispersion composition of the present invention.
  • FIG. 3 is a cross-sectional view schematically showing still another preferred embodiment of a production apparatus used in the method for producing an organic particle dispersion composition of the present invention.
  • FIG. 4-1 is a front view schematically showing an example of a dissolver stirring blade used in the method for producing an organic particle dispersion composition of the present invention.
  • FIG. 4-2 This is a drawing-substituting photograph of the dissolver stirring blade shown in Fig. 41.
  • FIG. 5 A stirrer 1 composed of a rotatable turbine part used in the method for producing an organic particle dispersion composition of the present invention and a fixed stator part with a slight gap around it. It is sectional drawing which shows an example schematically.
  • FIG. 6 is an explanatory diagram showing a structural example of an ultrafiltration device used in the method for producing an organic particle dispersion composition of the present invention.
  • FIG. 7 is an apparatus explanatory view schematically showing an example of a preferred embodiment of a production apparatus used in the production method of the present invention.
  • the present invention relates to an organic particle precipitation method for obtaining organic particles by injecting an organic material dissolved in a good solvent into a poor solvent preferably controlled in stirring conditions and temperature, and the organic particle precipitation method
  • the present invention relates to a method for efficiently concentrating organic particles produced by the above, and particularly to a method for producing an organic particle dispersion composition by removing unnecessary ions.
  • the present invention also relates to a method for producing an organic particle dispersion composition that does not change the particle size and monodispersity of organic particles in the concentration step, and that can be easily redispersed when the organic particles aggregate due to concentration.
  • the present invention will be described in detail.
  • the organic material used as the organic particles is not particularly limited as long as it can be produced by a conventional reprecipitation method.
  • Powerful organic hydrocarbons such as organic pigments, organic dyes, or polymer compounds are particularly preferable. A combination of these may also be used.
  • the organic pigment is not limited in terms of hue.
  • perylene pigments such as CI Pigment Red 190 (CI No. 71140), CI Pigment Red 224 (CI No. 71127), CI Pigment Noorette 29 (CI No. 711 29), CI Pigment Orange 43 (CI No. 71105), or perinone pigments such as CI Pigment® Red 194 (CI No. 71100), CI Pigment® Noorette 19 (CI No.
  • CI Pigment Nooret 42 CI CI pigment red 122 (CI number 73915), CI pigment red 192, CI pigment red 202 (CI number 73907), CI pigment red 207 (CI number 73900, 73906), or CI CI pigment red 209 ( CI No. 73905) quinacridone pigment, CI Pigment Red 206 (CI No. 73900, 73920), CI Big Men Orange 48 (CI No. 73900, 73920), CI Big Men Orange 49 (CI No. 73900, 73920), etc. Quinacridonequinone series C. I. Pigment Yellow 147 (CI No.
  • Pigment Red 185 (CI number 12516) and other benzimidazole pigments, CI Pigment Yellow 93 (CI number 20710), CI Pigment Yellow 94 (CI number 20038), CI Pigment Yellow 95 (CI number 20034) CI big yellow 128 (CI number 20037), CI big yellow 166 (CI number 20035), CI big orange 34 (CI number 21115), CI big orange 13 (CI number 21110), CI big blue Orange 31 (CI number 20050), C.I.Bigmen ⁇ Red 144 (CI number 20735), CI Bigmen ⁇ Red 166 (CI number 20 730), CI Pigment Red 220 (CI No. 20055), CI Big Pigment Red 221 (C.I.No.
  • CI Pigment Red 242 (CI No. 20067), CI Pigment Red 248, CI Pigment Red 262 or CI pigment brown 23 (CI number 2 0060) and other disazo condensation pigments, CI pigment yellow 13 (CI number 21100), CI pigment yellow 83 (CI number 21108), or CI pigment yellow 18 8 (CI number 21094), etc., CI pigment red 187 (CI number 12 486), CI pigment red 170 (CI number 12475), CI big men yellow 74 (CI number 11714), CI big men yellow 150 (CI number 48545), CI Pigment Red 48 (CI number 15865), CI Pigment Red 53 (CI number 15585), CI Pigment ⁇ Orange 64 (CI number 12760), or.
  • Azo pigments such as I. Big Men ⁇ Red 247 (C.I.No. 15915), indantron pigments such as CI Big Men ⁇ Blue 60 (CI No. 69800), CI Pigment Green 7 (CI No. 74260), CI Pigment Green 36 (CI number 74265), Pigment Green 37 (CI number 74255), Pigment Blue 16 (CI number 74100), CI Pigment Blue 75 (CI number 74160: 2), or 15 (CI number 74160) Phthalocyanine pigments such as CI pigment blue 56 (CI number 42800), or the like.
  • I. Big Men ⁇ Blue 61 CI No. 42765: 1), etc., triaryl carbo-based pigments, CI Pigment Violet 23 (CI No.
  • Dioxazine pigments such as CI Pigment Red 177 (CI No. 65300), CI Big Men Men Red 254 (CI No. 56110), CI Big Men Men Red 255 (CI No.
  • two or more kinds of organic pigments or solid solutions of organic pigments can be used in combination.
  • organic dyes include azo dyes, cyanine dyes, merocyanine dyes, and coumarin dyes.
  • polymer compound examples include polydiacetylene and polyimide.
  • the good solvent is not particularly limited as long as it can dissolve the organic pigment to be used and is compatible with or uniformly mixed with the poor solvent used in preparing the organic pigment particles.
  • the solubility of the organic pigment in a good solvent is preferably such that the solubility of the organic material is 0.2% by mass or more, and more preferably 0.5% by mass or more. This solubility may be the solubility when dissolved in an acidic or alkaline manner.
  • the compatibility or homogeneous mixing of the good solvent with the poor solvent is preferably 30% by mass or more, more preferably 50% by mass or more. ,.
  • the good solvent examples include an aqueous solvent (for example, water or hydrochloric acid, sodium hydroxide aqueous solution), alcohol solvent, amide solvent, ketone solvent, ether solvent, aromatic solvent, carbon disulfide. , Aliphatic solvents, nitrile solvents, sulfoxide solvents, halogen solvents, ester solvents, ionic liquids, mixed solvents thereof, and the like, aqueous solvents, alcohol solvents, ester solvents, sulfoxide solvents.
  • a water-based solvent in which a solvent or an amide solvent is preferred, a sulfoxide solvent or an amide solvent in which a sulfoxide solvent or an amide solvent is more preferred is particularly preferred.
  • Examples of the alcohol solvent include methanol, ethanol, isopropyl alcohol, n-propyl alcohol, 1-methoxy 2-propanol and the like.
  • Examples of amide solvents include N, N dimethylformamide, 1-methyl-2-pyrrolidone, 2 pyrrolidinone, 1,3 dimethyl-2-imidazolidinone, 2 pyrrolidinone, ⁇ -prolactam, formamide, ⁇ -methylformamide, Acetamide, ⁇ -methylacetamide, ⁇ , ⁇ ⁇ ⁇ dimethylacetamide, ⁇ methylpropanamide, hexamethylphosphoric tri Examples include amides.
  • Examples of the ketone solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • Examples of the ether solvent include dimethyl ether, jetyl ether, tetrahydrofuran and the like.
  • Examples of the aromatic solvent include benzene and toluene.
  • Examples of the aliphatic solvent include hexane.
  • the nitrile solvent include acetonitrile.
  • Examples of the sulfoxide solvent include dimethyl sulfoxide, jetyl sulfoxide, hexamethylene sulfoxide, sulfolane and the like.
  • Examples of the halogen solvent include dichloromethane and trichloroethylene.
  • ester solvent examples include ethyl acetate, ethyl lactate, and 2- (1-methoxy) propyl acetate.
  • ionic liquid examples include a salt of 1-petitor 3-methylimidazolium and PF-.
  • the concentration of the organic material solution in which the organic material is dissolved in the good solvent is preferably in the range of the saturated concentration of the organic material to the good solvent or the lZioo range under the dissolution conditions.
  • the conditions for preparing the organic material solution can be selected from a range of normal pressure to subcritical and supercritical conditions, with no particular restrictions on the conditions for preparing the organic material solution.
  • the temperature at normal pressure is preferably 10 to 150 ° C, more preferably 5 to 130 ° C, and particularly preferably 0 to 100 ° C.
  • the organic material is uniformly dissolved in a good solvent, but it is also preferable that the organic material is dissolved in an acidic or alkaline manner.
  • a pigment having an alkaline and dissociable group in the molecule it is alkaline, and when there is no alkaline and dissociable group and there are many nitrogen atoms in the molecule where protons can easily be added, acidity is used.
  • quinacridone, diketopyrrolopyrrole, and disazo condensation pigments are alkaline, and phthalocyanine pigments are acidic.
  • the base used for the alkaline dissolution is an inorganic base such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, or barium hydroxide, or a trialkylamine.
  • Power which is an organic base such as diazabicycloundecene (DBU) and metal alkoxide, preferably an inorganic base.
  • DBU diazabicycloundecene
  • metal alkoxide preferably an inorganic base.
  • the amount of the base used is an amount capable of uniformly dissolving the pigment, and is not particularly limited.
  • an inorganic base it is preferably 1.0 to 30 molar equivalents relative to the organic material, more preferably 1.0 to 25 molar equivalents, and even more preferably 1.0 to 20 molar equivalents.
  • an organic base it is preferably 1.0 to: LOO molar equivalent, more preferably 5.0 to 100 molar equivalent, and further preferably 20 to 100 molar equivalent with respect to the organic material.
  • the acid used in the case of acidic dissolution is preferably an inorganic acid such as sulfuric acid, hydrochloric acid, or phosphoric acid, or an organic acid such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • an inorganic acid such as sulfuric acid, hydrochloric acid, or phosphoric acid
  • an organic acid such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, or trifluoromethanesulfonic acid.
  • sulfuric acid is preferably sulfuric acid.
  • the amount of the acid used is an amount that can dissolve the organic material uniformly, and is not particularly limited. Regardless of the inorganic acid or organic acid, it is preferably 3 to 500 molar equivalents, more preferably 10 to 500 molar equivalents, still more preferably 30 to 200 molar equivalents relative to the organic material.
  • the poor solvent is not particularly limited as long as it does not dissolve the organic pigment to be used, is compatible with the good solvent used in the preparation of the organic pigment particles, or is mixed uniformly.
  • the poor solvent when the poor solvent is compatible with the organic material solution in this way, it acts on the organic material molecules in the organic material solution, and the organic material is deposited.
  • the solubility of the organic material in the poor solvent is preferably 0.02% by mass or less, more preferably 0.01% by mass or less.
  • the preferred range of compatibility or uniform mixing of the poor solvent with the good solvent is as described above.
  • the poor solvent examples include aqueous solvents (for example, water or hydrochloric acid, sodium hydroxide aqueous solution), alcohol solvents, ketone solvents, ether solvents, aromatic solvents, carbon dioxide, fatty acids Group solvents, nitrile solvents, halogen solvents, ester solvents, ionic liquids, mixed solvents thereof and the like, and aqueous solvents, alcohol solvents, and ester solvents are preferred.
  • aqueous solvents for example, water or hydrochloric acid, sodium hydroxide aqueous solution
  • alcohol solvents for example, ketone solvents, ether solvents, aromatic solvents, carbon dioxide, fatty acids
  • Group solvents nitrile solvents, halogen solvents, ester solvents, ionic liquids, mixed solvents thereof and the like
  • aqueous solvents, alcohol solvents, and ester solvents are preferred.
  • Examples of the alcohol solvent include methanol, ethanol, isopropyl alcohol, n-propyl alcohol, 1-methoxy 2-propanol and the like.
  • Keto Examples of the organic solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • Examples of the ether solvent include dimethyl ether, jetyl ether, and tetrahydrofuran.
  • Examples of the aromatic solvent include benzene and toluene.
  • Examples of the aliphatic solvent include hexane.
  • Examples of the nitrile solvent include acetonitrile.
  • Examples of the halogen solvent include dichloromethane, trichloroethylene, and the like.
  • ester solvent examples include ethyl acetate, ethyl lactate, 2- (1-methoxy) propyl pyracetate, and the like.
  • ionic liquid examples include a salt of 1-butyl-3-methylimidazolium and PF.
  • Examples of the solvent used as the supercritical fluid or subcritical fluid preferably used in the production method of the embodiment of the above (2) include, for example, water, alcohol compound solvent, ketone compound solvent, monolithic compound solvent, aromatic compound solvent. , Carbon disulfide, aliphatic compound solvent, nitrile compound solvent, sulfoxide compound solvent, halogen compound solvent, ester compound solvent, ionic solution, or a mixed solvent of two or more of these, water, alcohol compound solvent Ketone compound solvents, aromatic compounds and nitrile compound solvents are preferred. Water, ketone compound compounds solvents and aromatic compound solvents are more preferred.
  • the conditions for making the solvent a supercritical fluid or subcritical fluid may be appropriately determined depending on the solvent to be used (in the present invention, "supercritical fluid” means a critical temperature or higher and a critical temperature).
  • a subcritical fluid is a force in which only one of temperature and pressure reaches a critical state, or the other is not in a critical state, or both temperature and pressure are in a critical state.
  • the temperature does not reach, but at least one of temperature and pressure is sufficiently higher than normal temperature and close to the critical state.
  • the pressure is preferably 2 to 30 MPa. 3 to 25 MPa is more preferable. 4 to 20 MPa is particularly preferable.
  • the temperature is preferably 150 to 400 ° C, more preferably 180 to 350 ° C, and particularly preferably 200 to 300 ° C.
  • the amount of pigment dissolved in the supercritical fluid or subcritical fluid depends on the type of solvent and pigment used, but for example, 0.1 kg or more in 1 kg of supercritical fluid or subcritical fluid. It is preferable to dissolve pigments of Og or less. It is more preferable to dissolve 1 mg to 50 g of pigment.
  • a precipitation solvent is used as a poor solvent.
  • Preferred precipitation solvents include, for example, water, alcohol compound solvents, ketone compound solvents, monolithic compound solvents, aromatic compound solvents, carbon disulfide, aliphatic compound solvents, nitrile compound solvents, sulfoxide compound solvents. , Halogen compound solvent, ester compound solvent, ionic solution, or a mixed solvent of two or more of these, water, alcohol compound solvent, ketone compound solvent, ester compound solvent, aromatic compound solvent, halogen compound Water, alcohol compound solvents, and ketonic compound solvents are more preferred.
  • a polymer compound that can be preferably used in the production method of the present invention refers to an organic compound having a mass average molecular weight of 1000 or more, although there is no particular upper limit).
  • the mass average molecular weight is practically 500,000 or less, preferably 100,000 or less, more preferably 50,000 or less.
  • the production method of the present invention is preferred.
  • the polymer compound that can be used has a mass average molecular weight of 1000 or more, and is preferably a polymer compound represented by the following general formula (1).
  • a 1 is an acidic group, a group having a basic nitrogen atom, a urea group, a urea group, a group having a coordinating oxygen atom, or a hydrocarbon group having 4 or more carbon atoms.
  • An organic group, which may have a substituent, represents a monovalent organic group containing an organic dye structure or a heterocyclic ring.
  • n A 1 may be the same or different.
  • a 1 is not particularly limited, and examples of the “monovalent organic group having an acidic group” include a carboxylic acid group, a sulfonic acid group, a monosulfate group, and a phosphoric acid group. And monovalent organic groups having a monophosphate group and a boric acid group. Further, as the “monovalent organic group having a group having a basic nitrogen atom”, for example, a monovalent organic group having an amino group (one NH 3), a substituted imino group (one NHR 8 , —NR 9 R 1C > ) Monovalent organic group having
  • R 8 , R 9 and R 1G each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms.
  • the “monovalent organic group having a urea group” is, for example, —NHCONHR (where R 15 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, 6 to 20 carbon atoms) An aryl group of 7 to 30 carbon atoms).
  • Examples of the “monovalent organic group having a urethane group” include: —NHCOOR 16 , —OCO NHR 17 (wherein R 16 and R 17 are each independently an alkyl group having 1 to 20 carbon atoms, carbon number) Represents an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms.).
  • Examples of the “group having a group having a coordinating oxygen atom” include a group having an acetylethylacetonate group and a group having a crown ether.
  • Examples of the “group having a hydrocarbon group having 4 or more carbon atoms” include an alkyl group having 4 or more carbon atoms (for example, octyl group, dodecyl group, etc.), an aryl group having 6 or more carbon atoms (for example, a phenyl group, Naphthyl group) and aralkyl groups having 7 or more carbon atoms (for example, benzyl group). At this time, there is no upper limit to the number of carbon atoms, but it is preferably 30 or less.
  • Examples of the “group having an alkoxysilyl group” include groups having a trimethoxysilyl group, a triethoxysilyl group, and the like.
  • Examples of the “group having an epoxy group” include a group having a glycidyl group and the like.
  • Examples of the “group having an isocyanate group” include a 3-isocyanatopropyl group.
  • Examples of the “group having a hydroxyl group” include a 3-hydroxypropyl group.
  • a 1 a monovalent organic group having an acidic group, a group having a basic nitrogen atom, a urea group, and a hydrocarbon group having 4 or more carbon atoms, a group selected. Preferably it is.
  • the organic dye structure or heterocyclic ring is not particularly limited, and more specifically, examples of the organic dye structure include phthalocyanine compounds, insoluble azo compounds, azo lake compounds, anthraquinones. Compounds, quinacridone compounds, dioxazine compounds, diketopyrrolopyrrole compounds, anthrapyridine compounds, ansanthrone compounds, indanthrone compounds, flavanthrone compounds, perinone compounds, perylene compounds, thioindigo compounds, etc. It is done.
  • heterocyclic ring examples include thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane, pyrazole, pyrazoline, vilazolidin, imidazole, oxazole, thiazole, oxazidazole, triazole, thiadiazole, pyran, pyridine, piperidine.
  • the organic dye structure or the heterocyclic ring may have a substituent which may have a substituent.
  • substituent for example, alkyl groups having 1 to 20 carbon atoms such as methyl group and ethyl group, aryl groups having 6 to 16 carbon atoms such as phenyl group and naphthyl group, hydroxyl groups, amino groups, carboxyl groups, sulfones.
  • 1 to 6 carbon atoms such as amide group, N-sulfolamide group, and acetoxy group, alkoxy groups having 1 to 6 carbon atoms such as methoxy group and ethoxy group, halogen atoms such as chlorine and bromine, C2-C7 alkoxy carbonyl groups such as methoxy carbo yl group, ethoxy carbo yl group, cyclohex oxy carbo yl group, etc.
  • Carbonate ester group such as cyano group, t-butyl carbonate, etc. Can be mentioned.
  • the A 1 is preferably a monovalent organic group represented by the following general formula (4).
  • B 1 is an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, A group selected from an alkoxy silyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or an organic dye structure or a heterocyclic ring which may have a substituent.
  • R 18 represents a single bond or an alvalent organic or inorganic group. Represents a linking group. al represents 1 to 5, and al B 1 may be the same or different.
  • B 1 has the same meaning as A 1 in formula (4), and the preferred embodiment is also similar.
  • the organic dye structure or heterocyclic ring include phthalocyanine compounds and insoluble azo compounds.
  • Organic dye structures such as thioindigo compounds such as thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane, pyrazole, pyrazoline, virazolidine, imidazole, oxazole, thiazole, oxadiazole, triazole, thiadiazole, pyran, pyridine
  • the organic dye structure or heterocyclic ring may have a substituent.
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group. , Phenyl groups, naphthyl groups and the like having 6 to 16 carbon atoms such as aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfolamide groups, and acetoxy groups.
  • alkoxy group having 1 to 6 carbon atoms such as methoxy group, ethoxy group, halogen atom such as chlorine, bromine, methoxy carbo yl group, ethoxy carbo yl group, cyclohex oxy carbo yl group, etc.
  • R 18 represents a single bond or an al + monovalent linking group, and al represents 1 to 5.
  • the linking group R 18 includes 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0. Groups comprising from 20 to 20 sulfur atoms are included, which may be unsubstituted or further substituted.
  • R 18 is preferably an organic linking group.
  • R 18 include the following structural units or groups formed by combining the structural units.
  • R 1B has a substituent
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group and a naphthyl group having 6 to 6 carbon atoms.
  • Up to 16 carbon atoms such as aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfo-lumamide groups, acetoxy groups, etc.
  • 1 to 6 carbon atoms such as acyloxy groups, methoxy groups, ethoxy groups, etc.
  • Alkoxy groups of up to 6 carbon atoms halogen atoms such as chlorine and bromine, alkoxycarbon groups of up to 2 to 7 carbon atoms such as methoxycarbonyl groups, ethoxycarbonyl groups, cyclohexylcarbonyl groups, etc.
  • alkoxycarbon groups of up to 2 to 7 carbon atoms such as methoxycarbonyl groups, ethoxycarbonyl groups, cyclohexylcarbonyl groups, etc.
  • Examples include cyano groups and ester carbonate groups such as t-butyl carbonate.
  • R 1 represents an (m + n) -valent linking group. m + n satisfies 3 ⁇ : L0.
  • Examples of the (m + n) -valent linking group represented by R 1 include: 1 to: L00 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 From 1 to 200 hydrogen atoms, and from 0 to 20 sulfur atomic groups are included, which may be unsubstituted or further substituted.
  • R 1 is preferably an organic linking group.
  • R 1 include the structural units (t-1) to (t-34) or a group composed of a combination of the structural units (which may form a ring structure). ⁇ .)
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group and a naphthyl group having 6 to 6 carbon atoms. Carbon number up to 16 carbon atoms such as aryl group, hydroxyl group, amino group, carboxyl group, sulfonamido group, N-sulfol amide group, acetooxy group, etc.
  • R 2 represents a single bond or a divalent linking group.
  • R 2 includes: 1 to: LOO carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 to Up to 20 sulfur nuclear power groups are included, which may be unsubstituted or further substituted.
  • R 2 is preferably an organic linking group.
  • R 2 include the structural units of the above t-3, 4, 7-18, 22-26, 32, 34, or groups configured by combining the structural units.
  • R 2 has a substituent
  • substituents include an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group and a naphthyl group having 6 to 6 carbon atoms.
  • Carbon number up to 16 carbon atoms such as aryl group, hydroxyl group, amino group, carboxyl group, sulfonamido group, N-sulfol amide group, acetooxy group, etc.
  • alkoxy groups such as halogen atoms such as chlorine and bromine, methoxy carbo yl groups, ethoxy carbo yl groups, cyclohexyl carboxy groups, etc.
  • carbonic acid ester groups such as t-butyl carbonate.
  • m represents 1 to 8. As m, 1-5 is preferable, 1-3 is more preferable, and 1-2 is particularly preferable.
  • N represents 2-9.
  • n is preferably 2 to 8 forces S, more preferably 3 to 6 with 2 to 7 being more preferable.
  • P 1 represents a polymer skeleton and can be selected from ordinary polymers according to the purpose and the like.
  • the polymer skeleton is composed of a polymer or copolymer of a bull monomer, an ester polymer, an ether polymer, a urethane polymer, an amide polymer, an epoxy polymer, a silicone polymer, and these.
  • a modified product or copolymer for example, a copolymer of a polyether Z polyurethane copolymer, a polymer of a polyether z butyl monomer, etc. (any of random copolymer, block copolymer, graft copolymer) May be present).
  • a polymer or copolymer of a bulle monomer Selected from the group consisting of a polymer or copolymer of a bulle monomer, an ester polymer, an ether polymer, a urethane polymer, and a modified product or a copolymer thereof.
  • Particularly preferred are polymers or copolymers of vinyl monomers, at least one of which is more preferred.
  • the polymer is preferably soluble in an organic solvent. If the affinity with the organic solvent is low, for example, when used as a pigment dispersant, the affinity with the dispersion medium is weakened, and it may not be possible to secure a sufficient adsorption layer for dispersion stability.
  • a high molecular compound represented by the following general formula (2) is more preferable.
  • the general formula (2) has the same meaning as A 1 in ⁇ or the general formula (1) is the same also its concrete preferred embodiment, specific examples of the organic dye structure, Heterocycles that are more preferred are phthalocyanine compounds, azo lake compounds, anthraquinone compounds, dioxazine compounds, diketopyrrolopyrrol compounds, imidazole, triazole, pyridine, piperidine, Monoreforin, triazine, isoindoline, isoindolinone, benzimidazolone, benzothiazole, succinimide, phthalimide, naphthalimide, hydantoin, indole, quinoline, carbazole, atalidine, attaridone and anthraquinone are more preferred.
  • the substituent which may have a substituent as in A 1 is the same as that in A 1 , and the preferred embodiment is also the same.
  • a 2 the monovalent organic group represented by the general formula (4) is preferred, and details and specific examples, preferred and embodiments of the organic group are the same.
  • R 3 represents a (x + y) -valent linking group. Represented by R 3 (x
  • + y) valent linking groups include 1 to 60 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 100 hydrogen atoms, and Groups comprising 0 to 20 sulfur atoms are included and may be unsubstituted or further substituted.
  • the linking group of the represented by R 3 (x + y) value has the same meaning as the linking group of (m + n) valent in the R 1, it is the same a preferred embodiment thereof. Further, specific examples include the same structural unit as described above or a group constituted by combining the structural units.
  • the linking group represented by R 3 is preferably an organic linking group. Preferred specific examples of the organic linking group are shown below. However, the present invention is not limited to these.
  • R 3 has a substituent
  • substituents include carbon such as an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group, and a naphthyl group. Number 6 to 16 aryl groups, hydroxyl groups, amino groups, carboxyl groups, sulfonamido groups, N-sulfolamide groups, acetoxy groups, etc.
  • acyl groups having 1 to 6 carbon atoms such as acyl groups having 1 to 6 carbon atoms, methoxy groups, ethoxy groups, etc. C1-C6 alkoxy groups, halogen atoms such as chlorine and bromine, methoxycarbol groups, ethoxycarbon groups, cyclohexylcarboxy groups, etc.
  • -Carbonate group such as -l group, cyano group and t-butyl carbonate.
  • R 4 and R 5 each independently represents a single bond or a divalent linking group.
  • Preferred examples include SO or a divalent group in which two or more of these groups are combined.
  • the R 19 and R 2G is, independently,. Represents a hydrogen atom or a number 1-4 ⁇ alkyl group carbon atoms) is preferably 0 Among these organic linking group.
  • R 4 a linear or branched alkylene group, an aralkylene group, OC (
  • the divalent group combined above is particularly preferred.
  • R 5 a single bond, a linear or branched alkylene group, Ararukiren group, -O
  • a divalent group in which two or more of these groups are combined is particularly preferred.
  • R 5 has a substituent
  • substituents include carbon such as an alkyl group having 1 to 20 carbon atoms such as a methyl group and an ethyl group, a phenyl group, and a naphthyl group.
  • Number 6 Up to 16 carbon atoms such as aryl group, hydroxyl group, amino group, carboxyl group, sulfonamido group, N-sulfolamide group, acetoxy group, etc. carbon number up to 1-6, such as acyloxy group, methoxy group, ethoxy group, etc.
  • alkoxy groups such as halogen atoms such as chlorine and bromine, methoxy carbo yl groups, ethoxy carbo yl groups, cyclohexyl carboxy groups, etc.
  • y represents 1 to 8, 1 to 5 is preferable, and 1 to 3 is more preferable, and 1 to 2 is particularly preferable.
  • X represents 2-9, 2-8 are preferred, 2-7 are more preferred, and 3-6 are particularly preferred.
  • P 2 in the general formula (2) represents a polymer skeleton and can be selected from ordinary polymers according to the purpose and the like.
  • the preferred embodiment of the polymer is the same as P 1 in the general formula (1), and the preferred embodiment is also the same.
  • R 21 represents a hydrogen atom or a methyl group
  • 1 represents 1 or 2.
  • the polymer compound has a mass average molecular weight of lOOO or more, but the mass average molecular weight is 1000 to 500,000 force S preferred ⁇ , 3000 to 100000 preferred ⁇ , 5000 to 80000 force S more preferred. 7000 to 60000 is particularly preferable.
  • the mass average molecular weight is within the above range, the effects of the plurality of functional groups introduced at the ends of the polymer are sufficiently exerted, and the performance of adsorbing on the solid surface, micelle forming ability, and surface activity is excellent. Demonstrate.
  • a polymer compound is used as a pigment dispersant, good dispersibility and dispersion stability can be achieved.
  • the polymer compound represented by the general formula (1) (including the polymer compound represented by the general formula (2)) is not particularly limited, but can be synthesized by the following method. Of the following synthesis methods, the following synthesis methods such as 3, 4, 5, etc. are particularly preferred because of the ease of synthesis, and the following synthesis methods such as 2, 3, 4, 5 are more preferred.
  • a method in which a polymer in which a plurality of mercabtans are introduced at the terminal and a functional group in which a carbon-carbon double bond is introduced are reacted in the presence of a radical generator.
  • the polymer compound (preferably the polymer compound represented by the general formula (2)) used in the production method of the present invention is, for example, any one of the above 2, 3, 4, and 5 Although it can be synthesized by a method, it is more preferred to synthesize by the above method 5 because of ease of synthesis.
  • radical polymerization using a compound represented by the following general formula (3) as a chain transfer agent.
  • R 6 , R 7 , A 3 , g, and h are each R 3 in the general formula ( 2 ), It is synonymous with x and y, The preferable aspect is also the same.
  • the bull monomer is not particularly limited !, but, for example, (meth) acrylic acid esters, crotonic acid esters, buresters, maleic acid diesters, fumaric acid diesters, itaconic acid diesters , (Meth) acrylamides, butyl ethers, esters of butyl alcohol, styrenes, (meth) acrylonitrile and the like are preferable. Examples of such include the following compounds.
  • Examples of the (meth) acrylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, (meth) N-butyl acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid t- Butyl cyclohexyl, (meth) acrylic acid 2-ethylhexyl, (meth) acrylic acid t-octyl, ( Dodecyl (meth) acrylate, Octadecyl (meth) acrylate, Acetoxyethyl (meth) acrylate, Phenyl (meth) acrylate, 2-Hydroxyethyl (meth) acryl
  • crotonic acid esters examples include butyl crotonic acid and hexyl crotonic acid.
  • vinyl esters examples include butyl acetate, vinyl propionate, vinyl butyrate, vinyl methoxyacetate, vinyl benzoate, and the like.
  • maleic diesters examples include dimethyl maleate, diethyl maleate, and dibutyl maleate.
  • Examples of the fumaric acid diesters include dimethyl fumarate, jetyl fumarate, dibutyl fumarate, and the like.
  • Examples of the itaconic acid diesters include dimethyl itaconate, jetyl itaconate, and dibutyl itaconate.
  • Examples of the (meth) acrylamides include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) ) Acrylamide, N-n-butylacrylic (meth) amide, N-t-butyl (meth) acrylamide, N cyclohexyl (meth) acrylamide, N- (2-methoxyethyl ) (Meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-jetyl (meth) acrylamide, N-phenol (meth) acrylamide, N-benzyl (meth) acrylamide, (meth) atari Roylmorpholine, diacetone acrylamide, etc. are mentioned.
  • styrenes examples include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropylino styrene, butyl styrene, hydroxy styrene, methoxy styrene, butoxy styrene, acetoxy styrene, chloro styrene, dichloro styrene.
  • Examples thereof include low styrene, promostyrene, chloromethyl styrene, hydroxystyrene protected with a group that can be deprotected by an acidic substance (for example, t-Boc, etc.), methyl vinylbenzoate, and a-methylstyrene.
  • butyl ethers examples include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether.
  • (meth) acrylonitrile, heterocyclic groups substituted with vinyl groups for example, bullpyridine, bull pyrrolidone, bull force rubazole, etc.
  • N-buluformamide, N-bulacetoamide N-Buylimidazole, bull force prolatatone, etc. can be used.
  • butyl monomers having a functional group such as a urethane group, a urea group, a sulfonamide group, a phenol group, and an imide group can also be used.
  • a monomer having a urethane group or urea group can be appropriately synthesized by utilizing, for example, an addition reaction between an isocyanate group and a hydroxyl group or an amino group.
  • an addition reaction between an isocyanate group-containing monomer and a compound containing one hydroxyl group or a compound containing one primary or secondary amino group, or a hydroxyl group-containing monomer or primary or secondary amino group It can be appropriately synthesized by an addition reaction between a group-containing monomer and a monoisocyanate.
  • the above-mentioned radical monomers which may be polymerized by only one kind, or may be used in combination of two or more kinds, may be the usual bulle monomers. It can be obtained by polymerization according to a conventional method.
  • these vinyl monomers and chain transfer agents are dissolved in a suitable solvent, It is obtained by using a method (solution polymerization method) in which a radical polymerization initiator is added to the polymer and polymerized in a solution at about 50 ° C to 220 ° C.
  • Examples of suitable solvents used in the solution polymerization method can be arbitrarily selected depending on the monomers used and the solubility of the resulting copolymer.
  • solvents used in the solution polymerization method can be arbitrarily selected depending on the monomers used and the solubility of the resulting copolymer.
  • the radical polymerization initiator may be an azo such as 2,2'-azobis (isobutyoxy-tolyl) (AIBN) or 2,2, -azobis- (2,4, -dimethylbare-tolyl).
  • AIBN 2,2'-azobis (isobutyoxy-tolyl)
  • 2,2, -azobis- (2,4, -dimethylbare-tolyl) Compounds, peroxyacid compounds such as benzoyl peroxide, and persulfates such as potassium persulfate and ammonium persulfate can be used.
  • the compound represented by the general formula (3) can be synthesized by the following method or the like, but the following method 7 is more preferable because of ease of synthesis.
  • a method of converting a halide compound having a plurality of functional groups (A 1 or A 2 in the above general formula) into a mercabtan compound (a method of reacting with thiourea and hydrolyzing, a method of directly reacting with NaSH, Examples include a method of reacting with CH COSNa and hydrolyzing.
  • Preferred examples of the "functional group capable of reacting with a mercapto group" in Method 7 include an acid halide, an alkyl halide, an isocyanate, a carbon-carbon double bond, and the like.
  • the “functional group capable of reacting with a mercapto group” is a carbon-carbon double bond, and the addition reaction is synthesized by a radical addition reaction.
  • Carbon The carbon double bond is more preferably a mono- or di-substituted bur group in terms of reactivity with the mercapto group.
  • the above-mentioned “compound having 3 to 10 mercapto groups in one molecule” and the above “having an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, and a coordinating oxygen atom” A compound having at least one functional group selected from a group, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, and a hydroxyl group, and having a carbon-carbon double bond.
  • the radical addition reaction product includes, for example, the above-mentioned “compound having 3 to 10 mercapto groups in one molecule” and “acid group, group having basic nitrogen atom, urea group, urethane group, coordinating oxygen”.
  • Examples of preferable solvents used in the above method include "a compound having 3 to LO mercapto groups in one molecule", "an acidic group, a group having a basic nitrogen atom, a urea group, a Lethane group, group having a coordinating oxygen atom, hydrocarbon group having 4 or more carbon atoms, alkoxysilane A compound having at least one functional group selected from the group consisting of an alkyl group, an epoxy group, an isocyanate group, and a hydroxyl group, and a functional group capable of reacting with a mercapto group (for example, a carbon-carbon double bond), and It can be arbitrarily selected according to the solubility of the radical addition reaction product.
  • methanol, ethanol, propanol, isopropanol, 1 methoxy 2-propanol, 1-methoxy 2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, methoxypropyl acetate, lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, Kuroguchi Holm and Toluen are listed.
  • These solvents may be used as a mixture of two or more.
  • radical generators such as 2,2'-azobis (isobutyoroxy-tolyl) (AIBN) 2,2, -azobis (2,4, -dimethylvalerin-tolyl), and benzoyl peroxide can be used.
  • Peracids such as potassium persulfate and persulfates such as ammonium persulfate can be used.
  • the polymer compound is preferably a polymer compound having an acidic group, and more preferably a polymer compound having a lpoxyl group.
  • A Compound compound having a carboxyl group Particularly preferred are copolymer compounds containing at least one of the repeating units and (B) at least one of the derived repeating units.
  • a repeating unit derived from acrylic acid or methacrylic acid which is preferably a repeating unit represented by the following general formula (I):
  • a repeating unit derived from tacrylate is particularly preferred.
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R represents the following general formula (III)
  • R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxy group
  • R and R are hydroxyalkyl groups or an aryl group having 6 to 20 carbon atoms.
  • Each represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • i represents a number from 1 to 5.
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R represents the following general formula (V):
  • R represents an alkyl group having 2 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • R 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • j is a number between 1 and 5
  • the polymerization ratio of (A) a repeating unit derived from a compound having a carboxyl group and a repeating unit derived from the compound (B) having a carboxylic acid ester group is the total of repeating units (A). It is more preferable that the quantity ratio% to the number of repeating units is 3 to 40, and 5 to 35 is more preferable.
  • the molecular weight of the polymer means a mass average molecular weight unless otherwise specified.
  • the method for measuring the molecular weight of the polymer include a chromatography method, a viscosity method, a light scattering method, and a sedimentation rate method.
  • a mass average molecular weight measured by a chromatography method is used unless otherwise specified.
  • the polymer compound may be either water-soluble or oil-soluble, water-soluble and oil-soluble.
  • the polymer compound may be added in a solution in an aqueous solvent or an organic solvent, in a solid state, or a combination thereof.
  • Examples of the method of adding a solution dissolved in a solvent include, for example, a method of adding to an aggregated organic particle solution in a state dissolved in the same solvent as the solvent of the aggregated organic particle solution, and a compatibility with the solvent of the aggregated organic particle solution.
  • An example is a method in which it is dissolved in a different solvent.
  • the concentration of the polymer compound when added in a solution dissolved in a solvent is not particularly limited, but 1 to 70% by mass is preferable, 2 to 65% by mass is more preferable, and 3 to 60% by mass is particularly preferable. preferable.
  • Polymer compounds are added when organic nanoparticles are formed (or before and after) by organic particle precipitation, during extraction or concentration (or before and after), and when dispersed organic particles after concentration (or before and after). ) After these steps are completed, they may be added to any of them or a combination thereof.
  • a polymer compound having a mass average molecular weight of 1000 or more may be contained in the composition as a binder to be described later. For example, after concentrating the organic particle deposition liquid, finely dispersing the aggregated organic particles. Sometimes added It is preferable.
  • organic particles are formed in the presence of a polymer compound having an acidic group.
  • the polymer compound having an acidic group can be added to both or one of the poor solvents for adding the organic material solution and the organic material solution to produce organic particles.
  • the amount of the polymer compound added is preferably 0.1 to: L000 parts by mass, more preferably 5 to 500 parts by mass, when the organic particles contained in the aggregated organic particles are 100 parts by mass. 10 to 300 parts by mass are particularly preferred.
  • Examples of the high molecular compound having a molecular weight of 1000 or more include polybutyropyrrolidone, polyvinyl alcohol, polybutyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyacrylamide, butyl alcohol acetate butyl copolymer, poly Examples include a partially formalized butyl alcohol, a partially butylated butyl alcohol, a butylpyrrolidone acetate butyl copolymer, a polyethylene oxide z propylene oxide block copolymer, a polyamide, a cellulose derivative, and a starch derivative.
  • polymer compounds such as alginate, gelatin, albumin, casein, gum arabic, tonganto gum and lignosulfonate can also be used.
  • polymer compound having an acidic group examples include polyvinyl sulfate and condensed naphthalene sulfonic acid.
  • Examples of the polymer compound having a carboxyl group include polyacrylic acid, polymethacrylic acid, a cellulose derivative having a carboxyl group in a side chain, and the like.
  • a copolymer compound containing (A) at least one repeating unit derived from a compound having a carboxyl group and (B) at least one repeating unit derived from a compound having a rubonic acid ester group JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54-25957, JP-A-59-53836 and JP-A-59-71048
  • acrylic acid-acrylic acid ester copolymer methacrylic acid acrylic acid ester copolymer, acrylic acid-methacrylic acid ester copolymer, methacrylic acid-methacrylic acid ester copolymer, examples thereof include multi-component copolymers of acrylic acid or methacrylic acid, acrylic acid ester or methacrylic acid ester, and other bur compounds.
  • bur compound examples include styrene or substituted styrene (for example, butyl benzene and butyl benzene), bur naphthalene or substituted bur naphthalene, acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, and the like. Len is preferred.
  • polymer compounds may be used alone or in combination of two or more, and may be used in combination with a compound having a molecular weight of less than 1000.
  • the organic nanoparticle dispersion preferably contains 60% by mass or more of an organic solvent, more preferably 65% by mass or more.
  • an organic solvent there can be appropriately selected a normal medium force without particular limitation.
  • ester compound solvents, ketone compound solvents, and ester compound solvents, and ketone compound solvents are particularly preferred, which are ester compound solvents, alcohol compound solvents, aromatic compound solvents, aliphatic compound solvents, and ketone compound solvents. These may be used alone or in combination of two or more.
  • Examples of the ester compound solvent include 2- (1-methoxy) propyl acetate, ethyl acetate, and ethyl lactate.
  • Examples of the alcohol compound solvent include n-butanol and isobutanol.
  • Examples of the aromatic compound solvent include benzene, toluene, xylene and the like.
  • Examples of the aliphatic compound solvent include n-xane and cyclohexane.
  • Examples of the ketone compound solvent include methyl ethyl ketone, acetone, cyclohexanone, and the like.
  • a dispersant can be added to both or one of the poor solvent for adding organic material solution and organic material solution to produce organic particles.
  • Dispersant (1) Quickly adsorbs on the deposited pigment surface to form fine pigment particles And (2) has an effect of preventing these particles from aggregating again.
  • a dispersant a low-molecular or high-molecular dispersant having a ionic, cationic, amphoteric, nonionic or pigment property can be used.
  • the molecular weight of the polymer dispersant should be used without limitation as long as it can be dissolved uniformly in the solution. Force over S. Preferable ⁇ Molecular weight of 1,000 to 2,000,000, 5,000 to 5,000 1, 000,000 0 force S preferred ⁇ , 10,000-500,000 force S more preferred ⁇ 10, 000-100,000 force s, particularly preferred. (In the present invention, unless otherwise specified, molecular weight means mass average molecular weight.
  • a polymer compound is a polydisperse system and does not necessarily have the same molecular weight or particle weight.
  • the values obtained are average molecular weights averaged in some form, the main three being: 1) number average molecular weight ⁇ , 2) mass average molecular weight Mw, 3) Z average molecular weight Mz And the relationship of Mn ⁇ Mw ⁇ Mz holds.
  • polymer dispersant examples include polyvinyl pyrrolidone, polyvinyl alcohol, polybutyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyacrylamide, butyl alcohol, acetic acid butyl copolymer, poly Butyl alcohol partially formalized, polybull alcohol partially butyral, bull pyrrolidone acetic acid bull copolymer, polyethylene oxide z propylene oxide block copolymer, polyacrylate, polybul sulfate, poly (4 bull pyridine)
  • Examples include salts, polyamides, polyallylamine salts, condensed naphthalene sulfonates, cellulose derivatives, and starch derivatives.
  • N-acyl-N alkyl taurine salt fatty acid salt, alkyl sulfate ester salt, alkylbenzene sulfonate, alkyl naphthalene sulfonate, dialkyl sulfosuccinate , Alkyl phosphate ester Salt, naphthalenesulfonic acid formalin condensate, polyoxyethylene alkyl sulfate ester salt and the like.
  • N-acyl-N alkyltaurine salts are preferred.
  • the N-acyl N alkyltaurine salt those described in JP-A-3-273067 are preferable. These char-on dispersants can be used singly or in combination of two or more.
  • Cationic dispersants include quaternary ammonium salts, alkoxy Louis polyamines, aliphatic amine polyglycol ethers, aliphatic amines, aliphatic amines and fatty alcohol power induction. And diamines derived from fatty acids, imidazolines derived from fatty acids, and salts of these cationic substances. These cationic dispersants can be used alone or in combination of two or more.
  • the amphoteric dispersant is a dispersant having both the cation group part of the cation-dispersing agent in the molecule and the cation group part of the cation-dispersing agent in the molecule. .
  • Non-ionic dispersants include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, Examples thereof include oxyethylene alkylamine and glycerin fatty acid ester. Of these, polyoxyethylene alkylaryl ether is preferred. These nonionic dispersants can be used singly or in combination of two or more.
  • a pigment-based dispersant is defined as a pigment-based dispersant derived from an organic pigment as a parent substance and produced by chemically modifying the parent structure.
  • a pigment-based dispersant derived from an organic pigment as a parent substance and produced by chemically modifying the parent structure.
  • sugar-containing pigment dispersants for example, sugar-containing pigment dispersants, piperidyl-containing pigment dispersants, naphthalene or perylene-derived pigment dispersants, pigment dispersants having functional groups linked to the pigment parent structure via methylene groups, and chemically modified with polymers.
  • a compound represented by the general formula (I) described in JP-A-2000-239554 is also preferably used.
  • the amino group includes a primary amino group, a secondary amino group, and a tertiary amino group, and the number of the amino groups may be one or plural.
  • It may be a pigment derivative compound in which a substituent having an amino group is introduced into the pigment skeleton, or a polymer compound having a monomer having an amino group as a polymerization component. Examples of these include, for example, compounds described in JP-A Nos. 2000-239554, 2003-96329, 2001-31885, JP-A-10-339949, and JP-B-5-72943. Forces that are not limited to these
  • the amino group-containing dispersant used in the production method of the present invention is not limited thereto, but is represented by the following general formulas (Dl), (D3), and (D4). At least one selected from compounds can be used.
  • A-N N-X- Y
  • A represents a component capable of forming an azo dye together with X—Y.
  • A can be arbitrarily selected as long as it is a compound capable of forming an azo dye by coupling with a diazo-um compound. Specific examples of A will be shown below, but the present invention is not limited thereto.
  • X represents a single bond or a group selected from divalent linking groups represented by structural formulas of the following formulas (i) to (v).
  • Z represents a lower alkylene group.
  • Z is the force expressed as one (CH) —
  • the b represents an integer of 1 to 5, preferably 2 or 3.
  • NR is
  • —NR represents a lower alkylamino group, it is represented as —N (C H), and r is an integer of 1 to 4.
  • any of the heterocyclic groups represented by the following structural formula is preferred.
  • Z and -NR are each a lower alkyl group or an alcohol
  • a represents 1 or 2, preferably 2.
  • the compound represented by the general formula (Dl) can be synthesized, for example, by the method described in JP-A-2000-239554.
  • Q is an anthraquinone compound dye, an azo compound compound dye, a phthalocyanine compound dye, a quinacridone compound compound dye, a dioxazine compound compound dye, an anthrapyrimidine compound compound dye, an anthrone compound compound, an indanthrone compound Represents an organic dye residue selected from a dye, a flavanthrone compound dye, a pyranthrone compound dye, a perinone compound dye, a perylene compound dye, and a thioindigo compound dye, particularly an azo compound dye or a dioxazine compound dye. It is more preferred that it is an azo compound pigment. Yes.
  • X is CO—, —CONH-Y one, SO NH-Y one, or CH NHCOCH
  • NH-Y— represents CO— and —CONH-Y—.
  • Y represents an alkylene group or an arylene group which may have a substituent.
  • More preferred is phenylene, toluylene or hexylene.
  • R and R are each independently a substituted or unsubstituted alkyl group or R and R
  • a methyl group, an ethyl group, a propyl group, or a pyrrolidyl group including a nitrogen atom is preferable, and an ethyl group is more preferable!
  • Y represents —NH 2 or —O 2.
  • Z represents a hydroxyl group or a group represented by the general formula (D3a), or when nl is 1, —NH 2 —X Q may be used.
  • ml represents an integer of 1 to 6, preferably 2 to 3.
  • nl represents an integer of 1 to 4, preferably 1 or 2.
  • the compound represented by the general formula (D3) is represented by the following general formula, for example.
  • the compound represented by the general formula (D3) is, for example, an amine compound having R and R and R
  • JP-B-5-72943 can also be referred to.
  • the graft copolymer may have at least an amino group and an ether group, and may contain other monomers as copolymer units.
  • the weight average molecular weight (Mw) of the graft copolymer is preferably 300 to 100,000 particles ⁇ , more preferably 5000 to 50,000 force! / ⁇ . If the mass average molecular weight (Mw) force is less than 3000, the aggregation of pigment nanoparticles cannot be prevented, and the viscosity may increase. When it exceeds 0000, the solubility in an organic solvent is insufficient, and the viscosity may increase.
  • the mass average molecular weight is a polystyrene-reduced mass average molecular weight measured by gel permeation chromatography (carrier: tetrahydrofuran).
  • the graft copolymer comprises: (i) a polymerizable oligomer having an ethylenically unsaturated double bond at a terminal; (ii) a monomer having an amino group and an ethylenically unsaturated double bond; (iii) It preferably contains at least a polymerizable monomer having an ether group as a copolymer unit, and (iv) optionally contains other monomers as copolymer units.
  • the content of the graft copolymer, (i) the polymerizable oligomer is preferably to be 15 to 98 mass 0/0 device 25 to 90 weight 0 / 0 is it forces Ri preferably fixture (ii) preferably be an amino group-containing monomer is 1 to 40 wt% instrument 5 to 3 0% by weight and is more preferably tool the (iii) the ether group
  • the polymerizable monomer is preferably 1 to 70% by mass, more preferably 5 to 60% by mass.
  • the content of the polymerizable oligomer is less than 15% by mass, a steric repulsion effect as a dispersant may not be obtained, and aggregation of pigment nanoparticles may not be prevented. In some cases, the ratio of the nitrogen-containing monomer is reduced, the adsorption ability to the pigment particles is lowered, and the dispersibility is not sufficient. If the content of the nitrogen-containing monomer is less than 1% by mass, the adsorption capacity for organic particles may be reduced and dispersibility may not be sufficient, and if it exceeds 40% by mass, the proportion of the polymerizable oligomer will decrease.
  • the solid repulsion effect as a dispersant cannot be obtained, and the aggregation of pigment particles may not be sufficiently prevented.
  • the content of the polymerizable monomer having an ether group is less than 1% by mass, the development suitability in the production of a color filter or the like may not be sufficient, and when it exceeds 70% by mass, the dispersant is used as a dispersant. Your ability may decline.
  • the polymerizable oligomer (hereinafter sometimes referred to as “macromonomer”) is an oligomer having a group having an ethylenically unsaturated double bond at the terminal.
  • the oligomer generally includes, for example, alkyl (meth) acrylate, hydroxy.
  • Cialkyl (meth) acrylate, styrene, acrylonitrile, butyl acetate, and butagen force At least one selected monomer force A homopolymer or a copolymer formed, and among them, alkyl (meth) acrylate Preferred are rate homopolymers or copolymers, polystyrene and the like.
  • these oligomers which may be substituted with a substituent are not particularly limited, and examples thereof include a halogen atom.
  • Preferred examples of the group having an ethylenically unsaturated double bond include a (meth) atalyloyl group, a bure group, and the like, and among these, a (meth) atalyloyl group is particularly preferred.
  • an oligomer represented by the following general formula (E6) is preferable.
  • R 61 and R 63 represent a hydrogen atom or a methyl group.
  • R 62 represents an alkylene group which may be substituted with an alcoholic hydroxyl group having 1 to 8 carbon atoms, and an alkylene group having 2 to 4 carbon atoms is preferable.
  • Y 6 is a phenyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, or —COOR 64 (where R 64 is an alcoholic hydroxyl group having 1 to 6 carbon atoms, halogen, Represents an optionally substituted alkyl group, a phenyl group, or an arylalkyl group having 7 to 10 carbon atoms.), A phenyl group or —COOR 64 (where R 64 is a carbon number of 1). Represents an alkyl group which may be substituted with ⁇ 4 alcoholic hydroxyl groups). q represents 20-200.
  • polymerizable oligomer examples include poly-2-hydroxyethyl (meth) atrelate, polystyrene, polymethyl (meth) acrylate, poly n-butyl (meth) acrylate, poly i butyl.
  • a (meth) acrylate, a copolymer thereof, and a polymer in which a (meth) taliloyl group is bonded to one of the molecular terminals is preferred.
  • the polymerizable oligomer may be a commercially available product or an appropriately synthesized one.
  • Preferred examples of the polymerizable oligomer in the present invention include, as specific examples, polymers of alkyl (meth) acrylate and copolymers of alkyl (meth) acrylate and polystyrene. And those having a number average molecular weight of 1000 to 20000 and having a (meth) atallyloyl group at the terminal.
  • Suitable examples of the amino group-containing monomer include at least one selected from compounds represented by the following general formula (E2).
  • R 21 represents a hydrogen atom or a methyl group.
  • R 22 represents an alkylene group having 1 to 8 carbon atoms, and among these, an alkylene group having 1 to 6 carbon atoms is preferable, and an alkylene group having 2 to 3 carbon atoms is particularly preferable.
  • X 2 represents N (R 23 ) (R 24 ), and one R 25 N (R 26 ) (R 27 ).
  • R 23 and R 24 represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
  • R 25 represents an alkylene group having 1 to 6 carbon atoms
  • R 26 and R 27 are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or phenyl. Represents a group.
  • - N (R 23) R 23 and R 24 of (R 24) is a hydrogen atom or 1 to 4 carbon atoms alkyl Le group or Hue - Le group preferably tool -R 25 - R 25 of N (R 26 ) (R 27 ) is preferably an alkylene group having 2 to 6 carbon atoms.
  • R 26 and R 27 are preferably an alkyl group having 1 to 4 carbon atoms.
  • R 31 has the same meaning as R 21 .
  • R 32 is synonymous with R 22 .
  • X 3 is synonymous with X 2 .
  • R 41 has the same meaning as R 21 .
  • X 4 is synonymous with X 2 — N
  • R 43 (R 43 ) (R 44 ) (where R 43 and R 44 are synonymous with R 23 and R 24 ), or -R 45 -N (R 46 ) (R 47 ) (where R 45 , R 46 and R 47 are synonymous with 5 , R 26 and R 27 , respectively.
  • Specific examples of the monomer represented by the general formula (E2) include dimethyl (meth) acrylamide, jetyl (meth) acrylamide, diisopropyl (meth) acrylamide, di-n-butyl (meth) acrylamide, di- — I-butyl (meth) acrylamide, morpholino (meth) acrylamide, piperidino (meth) acrylamide, N-methyl-2-pyrrolidyl (meth) acrylamide and N, N-methylphenol (meth) acrylamide (above ( (Meth) acrylamides); 2— (N, N-dimethylamino) ethyl (meth) acrylamide, 2- (N, N-demethylamino) ethyl (meth) acrylamide, 3 -— (N, N-demethylamino) propyl (meth) acrylamide, 3 -— (N, N-dimethylamino) propyl (meth) acryl
  • Suitable examples of the polymerizable monomer having an ether group include at least one selected from monomers represented by the following general formula ( E 1 ).
  • R 11 represents a hydrogen atom or a methyl group.
  • R 12 represents an alkylene group having 1 to 8 carbon atoms, and among them, an alkylene group having 2 to 3 carbon atoms, more preferably an alkylene group having 1 to 6 carbon atoms, is more preferable.
  • X 1 represents OR 13 or one OCOR 14 .
  • R 13 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenol group, or a phenyl group substituted with an alkyl group having 1 to 18 carbon atoms.
  • R 14 represents an alkyl group having 1 to 18 carbon atoms.
  • m3i represents 2 to 200, 5 ⁇ : L00 force preferred, 10 ⁇ : L00 force ⁇ Especially preferred! / ,.
  • the polymerizable monomer having an ether group can be appropriately selected from the usual intermediate forces that are not particularly limited as long as they have an ether group and are polymerizable.
  • the commercially available products include methoxypolyethylene glycol metatalylate (trade names: NK ester M-40G, M-90G, M-230G (above, manufactured by Toa Gosei Chemical Co., Ltd.); trade name: BLEMMER PME— 100, PME-200, PME-400, PME-1000, PME—2000, PME—4000 (Enomoto Yushi Co., Ltd.) Polyethylene glycol monometatalylate (trade name: Blemmer PE-90, PE 200, PE-350, manufactured by Nippon Oil & Fats Co., Ltd.), polypropylene glycol monometatalylate (trade name: Blemmer PP-500) , PP-800, PP-1000, manufactured by Nippon Oil & Fats Co., Ltd.), Polyethylene Glycol Polypropylene Glycol Monometatalylate (Brandmer 70 PEP-370B, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol polytetra M
  • the graft copolymer may further contain the other monomer as a copolymer unit, and the other monomer may be appropriately selected according to the purpose without any particular limitation.
  • Aromatic vinyl compounds eg, styrene, a-methylstyrene and butyltoluene
  • acrylic acid alkyl esters eg, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl) (Meth) acrylate and i-butyl (meth) acrylate
  • (meth) acrylate alkyl aryl ester eg, benzyl (meth) acrylate
  • glycidyl (meth) acrylate carboxylate butyl ester (eg Butyl acetate and propionate)
  • cyanide butyl eg, (meth) acrylonitrile and chloroformate trityl
  • Fine aliphatic conjugated diene
  • the content of the other monomer in the graft copolymer is, for example, 5 to
  • 70% by mass is preferred. When the content is less than 5% by mass, the physical properties of the coating film may not be controlled. When the content exceeds 70% by mass, the ability as a dispersant may not be sufficiently exhibited.
  • Preferred examples of the graft copolymer include:
  • the graft copolymer can be obtained by, for example, performing radical polymerization of the components to be the respective copolymer units in a solvent.
  • a radical polymerization initiator can be used, and a chain transfer agent (eg, 2-mercaptoethanol and dodecyl mercaptan) can be further used.
  • JP-A-2001-31885 can also be referred to for the pigment dispersant containing the graft copolymer.
  • the content of the dispersant may be in the range of 0.1 to L000 parts by mass with respect to 100 parts by mass of the pigment in order to further improve the uniform dispersibility and storage stability of the pigment particles. More preferably, it is in the range of 1 to 500 parts by mass, and still more preferably in the range of 5 to 20 parts by mass. If the amount is less than 1 part by mass, the dispersion stability of the organic nanoparticles may not be improved.
  • a dispersing agent may be used independently or may be used in combination of multiple things.
  • the organic particle of the present invention is a step of obtaining an organic particle by mixing an organic material solution obtained by dissolving an organic material in a good solvent and a poor solvent for the organic material (hereinafter also simply referred to as “poor solvent for organic particles”). (Hereinafter, this method is also referred to as “organic particle precipitation method”, and the organic particle liquid obtained by this method is referred to as “organic particle dispersion”).
  • the normal pressure can be selected from the subcritical and supercritical conditions.
  • the temperature at normal pressure is preferably ⁇ 30 to 100 ° C. ⁇ 10 to 60 ° C. is more preferable, and 0 to 30 ° C. is particularly preferable.
  • the method of mixing the organic material solution and the poor solvent it is preferable to add one organic material solution to the stirred poor solvent. Particularly preferred.
  • a pump or the like may be used for the addition, or it may not be used. Further, it may be added in the liquid or outside the liquid, but the addition in the liquid is more preferable.
  • One or more addition ports may be used for the submerged addition. It is preferable that the accessory diameter is 20 mm or less. More preferably, it is 10 mm or less.
  • the stirring speed when stirring one is preferably 100 to 10,000 rpm, more preferably 150 to 8000 rpm, and particularly preferably 200 to 6000 rpm.
  • the ratio of the organic material solution to the poor solvent is preferably 1Z50 to 2Z3 by volume ratio, 1Z40 to: LZ2 is more preferred, and 1Z20 to 3Z8 is particularly preferred.
  • the concentration of the dispersion liquid prepared as organic particles is not particularly limited as long as the organic particles can be dispersed, but it is more preferable that the particle force is in the range of 10 to 40,000 mg per 1000 ml of the dispersion solvent. Is in the range of 20-30000 mg, particularly preferably in the range of 50-25000 mg.
  • the conditions when the organic pigment-containing fluid and the precipitation solvent are mixed are not particularly limited, but the solubility of the pigment as the state is not the organic pigment-containing fluid in a supercritical state or subcritical fluid state. It is preferable that the conditions are such that the pigment is precipitated and the pigment is precipitated.
  • the mixing temperature is preferably lower than the supercritical temperature of the solvent used. For example, when using acetone, it is preferable to set the temperature within the range of 15 ° C to 180 ° C, more preferably 40 ° C to 180 ° C, and particularly preferably 60 ° C to 150 ° C. preferable.
  • the pressure at the time of mixing is preferably near the supercritical pressure of the solvent to be used or higher than the supercritical pressure.
  • the pressure is preferably 2 to 30 MPa, more preferably 3 to 25 MPa, and particularly preferably 4 to 20 MPa.
  • the mixing ratio between the organic pigment-containing fluid and the precipitation solvent is preferably 20: 1 to 1:20, more preferably 10: 1 to 1:10, and more preferably 5: 1 to 1: 5. preferable.
  • the particle concentration of the mixed liquid in which the organic pigment is precipitated is not particularly limited, but is preferably in the range of 0.01 to 500 mgZml, more preferably 0.1 to: in the range of LOOmgZml, particularly preferably 0. 5 ⁇ : It is in the range of LOmgZml.
  • a supercritical fluid or When using a field fluid it exhibits different properties from melting at room temperature and pressure. For example, the ability to dissolve poorly soluble materials such as facial materials is enhanced.
  • the particle size of organic particles there is a method of expressing the average size of the population by numerical values by measurement methods, but as a common method, the mode diameter indicating the maximum value of distribution, the integral distribution curve Median diameter corresponding to the median value of each other, various average diameters (number average, length average, area average, mass average, volume average, etc.), etc. in the present invention, unless otherwise specified. Means the number average diameter.
  • the average particle size of the organic particles (primary particles) contained in the organic particle dispersion used in the organic particle concentration method of the present invention is nanometer size, and the particle size is preferably 1 ⁇ to 1 / ⁇ ⁇ . More preferably, it is 1 to 200 nm. 2-: It is particularly preferable that LOOnm is 5 to 80 nm.
  • the formed particles may be crystalline particles, non-crystalline particles, or a mixture thereof.
  • the ratio ( ⁇ ) of the volume average particle size (Mv) and the number average particle size ( ⁇ ) is used as an index representing the monodispersity of the particles unless otherwise specified.
  • the monodispersity of particles (primary particles) contained in the organic particle dispersion used in the organic particle concentration method of the present invention that is, ⁇ / ⁇ is preferably 1.0 to 2.0, and preferably 1.0 to 1.8. Is more preferably 1.0 to 1.5.
  • Methods for measuring the particle size of organic particles include microscopy, mass method, light scattering method, light blocking method, electrical resistance method, acoustic method, and dynamic light scattering method. Particularly preferred.
  • Examples of the microscope used for the microscopy include a scanning electron microscope and a transmission electron microscope.
  • Examples of the particle measuring apparatus by the dynamic light scattering method include Nikkiso Co., Ltd. Nanotrac UPA-150, Otsuka Electronics Co., Ltd. dynamic light scattering photometer DLS-7000 series, and the like.
  • FIG. 11 is a schematic view of a production apparatus used as an embodiment in the present invention.
  • the organic material solution is continuously supplied from the supply pipe 14 into the mixing chamber 13 provided in the container 11.
  • the container 11 is filled with the poor solvent 11a
  • the mixing chamber 13 is provided under the surface of the poor solvent
  • the inside thereof is filled with the poor solvent.
  • the Balta poor solvent in the reaction vessel 11 is constantly convected across the mixing chamber 13 from below to above (in the direction of the arrow in the figure) by the action of stirring in the mixing chamber 13. Yes.
  • FIG. 1-2 is an enlarged partial sectional view schematically showing the mixing chamber 13 in an enlarged manner as an embodiment of the manufacturing apparatus of FIG. 1-1.
  • the organic material solution is supplied from the supply pipe 14 into the mixing chamber 13.
  • the mixing chamber 13 is formed by a casing 17 made of a rectangular cylinder having a constant cross-sectional area.
  • the upper end of the casing 17 is an open end, and a circular hole 18 is provided at the lower end so that the poor solvent in the mixer 13 It becomes connected with the poor solvent.
  • the organic material solution supply pipe 14 is provided in a wall constituting the lower end of the casing 17 and opens toward the circular hole.
  • a stirring blade 12 is provided in the mixer 13, and the stirring blade is attached to a shaft 15 and is rotated by a motor (not shown). By the rotation of the stirring blade 12, the poor solvent is constantly circulated through the circular hole 18, and the downward force is always directed upward in the mixer 13.
  • the stirring blade 12 provided in the mixing chamber 13 must produce a desired mixing strength in the mixing chamber. This mixing strength is estimated to be an important operating factor for the size of the droplet when the organic material solution is mixed.
  • stirring blades 12 can be combined with other organic particles to form larger particles when the organic particles generated in the mixing space remain in the mixing chamber 13, or to the organic material solution supplied to the mixing chamber 13. It has the ability to quickly draw out the generated organic particles and quickly discharge them out of the mixing chamber 13 so that they do not become large particles when exposed. It is preferable to choose what to do!
  • any type can be used as long as the above object is achieved.
  • a turbine type, a fan turbine type or the like can be used.
  • the casing 17 is preferably composed of a rectangular tube as described above. By doing so, the corners of the casing 17 disturb the flow created by the stirring blades 12, and the mixing effect without requiring additional products such as baffles can be further enhanced.
  • Figure 13 shows another embodiment of the production apparatus of Figure 11 with two stirring blades in the mixing chamber.
  • FIG. 5 is an enlarged partial cross-sectional view of a mixer (mixing stirring blade 19a, discharging stirring blade 19b).
  • FIG. 2 is a cross-sectional view schematically showing another embodiment of the production apparatus used in the method for producing an organic particle dispersion composition of the present invention.
  • the organic material solution and the poor solvent are continuously supplied into the stirring tank 21a through the supply pipes 24a and 24b, respectively.
  • the organic particles generated in the stirring tank 21a remain in the stirring tank 21a, so that they are combined with other organic particles to become larger particles or exposed to the organic material solution supplied from the supply pipes 24a and 24b.
  • the generated organic particle dispersion is quickly withdrawn from the discharge pipe 23 so that large particles are not generated due to large particles.
  • FIG. 3 is a cross-sectional view schematically showing still another embodiment of the apparatus used in the method for producing an organic particle dispersion composition of the present invention.
  • the stirring device 50 includes two liquid supply ports 32 and 33 for allowing the organic material solution and the poor solvent to flow in, and a liquid discharge port 36 for discharging the mixed liquid after the stirring treatment, respectively.
  • a cylindrical stirring tank 38 provided, and a pair of stirring blades 41 and 42 as stirring means for controlling the stirring state of the liquid in the stirring tank 38 by being driven to rotate in the stirring tank 38. Become.
  • the agitation tank 38 includes a cylindrical tank body 39 whose central axis is directed in the vertical direction, and a seal plate 40 serving as a tank wall that closes the upper and lower opening ends of the tank body 39. Further, the agitation tank 38 and the tank body 39 are made of a nonmagnetic material having excellent magnetic permeability. 2 liquid supply The ports 32 and 33 are provided at a position near the lower end of the tank body 39, and the liquid discharge port 36 is provided at a position near the upper end of the tank body 39.
  • each stirring blade 41, 42 constitutes an external magnet 46 and a magnetic coupling C arranged outside the tank wall (seal plate 40) where the stirring blade 41, 42 is close. That is, the stirring blades 41 and 42 are coupled to the respective external magnets 46 by magnetic force, and are rotated in opposite directions by being driven by the independent motors 48 and 49. Operated.
  • the pair of stirring blades 41, 42 arranged opposite to each other in the tank 38 are provided with stirring flows having different directions as indicated by the wavy arrow (X) and the solid arrow (Y) in FIG. Form in tank 38. Since the stirring flows formed by the respective stirring blades 41 and 42 have different flow directions, they collide with each other to generate a high-speed turbulent flow in the tank 38 that promotes stirring in the tank 38, 38 prevents the flow in the steady state and prevents the formation of a cavity around the rotation axis of the stirring blades 41 and 42 even when the stirring blades 41 and 42 are rotated at high speed. It is possible to prevent the inconvenience that a steady flow flowing in the tank 38 along the inner peripheral surface of the stirring tank 38 is formed without being sufficiently affected. Therefore, the processing speed can be easily improved by the high-speed rotation of the stirring blades 41 and 42, and further, the liquid flow in the tank 38 becomes steady and liquid with insufficient stirring and mixing at that time. Can be prevented, and the degradation of the processing quality can be prevented.
  • the stirring blades 41 and 42 in the stirring tank 38 are connected to the motors 48 and 49 disposed outside the stirring tank 38 by the magnetic coupling C, the rotating shaft is connected to the tank wall of the stirring tank 38.
  • the stirring tank 38 can be made into a closed container structure without the insertion part of the rotating shaft, preventing leakage of the stirred and mixed liquid to the outside of the tank, and at the same time, lubricating oil for the rotating shaft. It is possible to prevent deterioration in processing quality due to (sealing liquid) or the like being mixed into the liquid in the tank 38 as an impurity.
  • an organic pigment particle can be produced not only in a batch method but also in a continuous flow method using a production apparatus having these configurations. It can handle mass production.
  • the generated organic particle dispersion is quickly discharged.
  • the ratio of the organic material solution and the poor solvent solution supplied into the stirring tank can be kept constant. For this reason, it becomes possible to make the solubility of the organic material of the dispersion liquid constant from the start of manufacture to the end of manufacture, and monodisperse organic particles can be stably produced.
  • the liquid flow in the tank becomes steady, preventing the organic particle dispersion liquid with insufficient stirring and mixing from being discharged, and the lubricating liquid (seal liquid) for the rotating shaft is used as an impurity as the liquid in the tank. By preventing it from being mixed in, monodispersed organic particles can be produced more stably.
  • the shearing force referred to in the present invention is a shear that the stirring blade exerts on droplets generated after the organic pigment solution is mixed in a poor solvent.
  • the shape of the stirring unit usable in the present invention is not particularly limited as long as it can be subjected to a high shearing force, but generally includes paddle blades, turbine blades, screw blades, fowler blades, etc.
  • An agitator, an emulsifier, and a disperser are preferably used in the agitating portion that is constituted by a turbine portion that can rotate and a fixed stator portion that is positioned with a small gap around it.
  • the dissolver blade is a special stirring blade having a function capable of forming a high shear force.
  • One example is schematically shown in the front view in FIG. 41, and a photograph in place of the drawing is shown in FIG.
  • a device having a stirring portion constituted by a turbine portion that can rotate as shown in FIG. 5 and a fixed stator portion that is positioned with a slight gap around the turbine portion is also preferably used.
  • the stirrer, emulsifier, and disperser include, for example, Histotron manufactured by Microtech-Thion Co., Ltd., T. K Homomixer manufactured by Tokushu Kika Kogyo Co., Ltd., and ULTRA-TURRAX manufactured by IKA.
  • the stirring speed at which the effects of the present invention can be manifested is a force that varies depending on the viscosity of the poor solvent, the temperature, the type of surfactant and the amount of additive, and a force of 100 to 10,000 rpm S, preferably 150 to 8000 rpm 200-6000rpm force S is more preferable. If the rotation speed is less than this range In other words, the effect of the present invention is not sufficiently exhibited. On the other hand, if it exceeds this range, bubbles are introduced into the poor solvent, which is not preferable.
  • the manufacturing apparatus used in the manufacturing method of the embodiment of the above (2) of the present invention is to mix a pigment dissolving fluid obtained by dissolving a pigment in a supercritical fluid or a subcritical fluid and a precipitation solvent to precipitate particles.
  • a pigment dissolving fluid obtained by dissolving a pigment in a supercritical fluid or a subcritical fluid and a precipitation solvent to precipitate particles.
  • FIG. 7 demonstrates an example of the preferable embodiment.
  • the supercritical fluid or subcritical fluid 101 is put in a container, and is pumped by the pump 104a, heated by the heater 106, and the pressure is adjusted by the back pressure valve 114.
  • the sample pipe 1 07 is injected through the mesh 109a.
  • the sample 103 such as the pigment that has been charged into the supercritical fluid or subcritical fluid injected into the supercritical fluid or subcritical fluid is dissolved, passes through the pigment dissolving fluid cache 109b, and is sent to the mixer 111. It is done.
  • the pigment-dissolved fluid sent by the pump 104a and the precipitation solvent 102 sent by the pump 104b are mixed, and the solvent composition and the solvent temperature change rapidly.
  • the nanoparticle dispersion produced in the mixer section is cooled to near room temperature with a cooling pipe 112 and can be taken out of the system as a nanoparticle dispersion 115 at normal temperature and normal pressure (note that arrow B in Fig. 7 is sent). Indicates the direction of the liquid).
  • the organic particle dispersion is desalted and concentrated to obtain an organic particle dispersion having a concentration suitable for a color filter coating liquid and an inkjet ink on an industrial scale. It is possible to produce.
  • the dispersion is concentrated by ultrafiltration. If the particle-containing liquid formed simply by the organic particle precipitation method is concentrated by ultrafiltration, the particle size distribution changes greatly during the concentration process.
  • the method for producing an organic particle dispersion composition of the present invention suppresses such a change in the particle size distribution, and enables efficient removal and concentration of salt that does not require force. Also after ultrafiltration, further vacuum freezing It is also very preferable to combine the methods of sublimating the solvent by freeze drying, concentrating and drying. Furthermore, you may combine with the concentration methods other than ultrafiltration.
  • an extraction solvent is added to and mixed with an organic particle dispersion, the organic particles are concentrated and extracted into the extraction solvent phase, and the concentrated extract is filtered through a filter or the like to obtain a concentrated particle liquid. Therefore, a method of precipitating and concentrating the organic particles, a method of drying and concentrating the solvent by heating or decompression, etc. are preferred. Or a combination of these is very preferably used.
  • concentration of organic particles after concentration 1 to 100% by mass is preferable 5 to: LOO% by mass is more preferable 10 to: LOO% by mass is particularly preferable.
  • a specific ultrafiltration method can be applied, for example, a method used for desalting / concentrating a silver halide emulsion.
  • Research Disclosure No. 10208 (1972), No. 13122 (1975) and No. 16 351 (1977) are known.
  • the pressure difference and flow rate which are important as operating conditions, can be selected with reference to the characteristic curve described in Haruhiko Oya's “Membrane Utilization Technology No. Book” Koshobo Publishing (1978), p275.
  • FIG. 6 shows a configuration example of an apparatus for performing ultrafiltration.
  • this apparatus has a tank 81 for storing the organic particle dispersion, a circulation pump 82 for circulating the dispersion in the tank 81, and a secondary liquid in the dispersion introduced by the circulation pump 82.
  • It has an ultrafiltration module 83 that removes generated organic salt as permeate.
  • the dispersion from which the permeated water has been separated is returned to the tank 81 again, and the same operation is repeated until the predetermined purpose of removing the by-product inorganic salt is achieved.
  • this device has a replenishment pure water measurement flow meter used to replenish a certain amount of solvent lost by permeate as pure water. 4 is installed, and a permeate flow meter 85 used to determine the amount of pure water replenishment is installed.
  • a reverse cleaning pump 86 is installed to introduce water for diluting the permeate.
  • the ultrafiltration membrane flat plate type, spiral type, cylindrical type, hollow fiber type, holo fiber type, etc., which are already incorporated as modules, include Asahi Kasei Co., Ltd., Daicel Chemical Co., Ltd., Toray Industries, Inc. Nitto Denko Co., Ltd. is commercially available, but a spiral type or hollow fiber type is preferred from the viewpoint of the total membrane area and detergency.
  • the molecular weight cut-off which serves as an index for the threshold value of the component that can permeate the membrane, must be determined from the molecular weight of the dispersant used, but the force after 5,000 to 50,000 is preferred. , More than 5,000 and less than 15,000.
  • the freeze-drying method is not particularly limited, and any method that can be used by those skilled in the art may be adopted.
  • a refrigerant direct expansion method, an overlapping freezing method, a heat medium circulation method, a triple heat exchange method, and an indirect heating freezing method can be mentioned, preferably a refrigerant direct expansion method, an indirect calothermal heat freezing method, more preferably an indirect heating freezing method.
  • the pre-freezing conditions are not particularly limited, but the sample to be lyophilized needs to be completely frozen.
  • Indirect heating freezing methods include small freeze dryer, FTS freeze dryer, LYOVA C freeze dryer, experimental freeze dryer, research freeze dryer, triple heat exchange vacuum freeze dryer, monocooling Lyophilizer and HULL lyophilizer are preferable, but preferably a small lyophilizer, a laboratory lyophilizer, a research lyophilizer, a monocooling lyophilizer, more preferably a small lyophilizer, A cooling freeze dryer may be used.
  • the temperature of lyophilization is not particularly limited, but is, for example, -190 to -4 ° C, preferably -120 to -20 ° C, more preferably about -80 to -60 ° C.
  • the pressure of lyophilization is not particularly limited, and can be appropriately selected by those skilled in the art. For example, 0.1 to 35 Pa, preferably 1 to 15 Pa, more preferably 5 to about LOPa.
  • the freeze-drying time is, for example, 2 to 48 hours, preferably 6 to 36 hours, and more preferably about 16 to 26 hours. However, these conditions can be appropriately selected by those skilled in the art.
  • the extraction solvent used for this concentration extraction is not particularly limited, but does not substantially mix with the dispersion solvent (for example, aqueous solvent) of the organic particle dispersion (in the present invention, it does not mix substantially)
  • Low solubility means 50% by mass or less is preferable, and 30% by mass or less is more preferable.
  • this extraction solvent must be a solvent that produces weak aggregation (re-dispersion is possible without applying high shearing force such as milling or high-speed stirring) in which organic particles can be re-dispersed in the extraction solvent. preferable.
  • the target organic particles are moistened with the extraction solvent without causing strong aggregation that changes the particle size, and the dispersion solvent such as water can be easily removed by filter filtration or the like.
  • the dispersion solvent such as water can be easily removed by filter filtration or the like.
  • the extraction solvent is preferably an ester solvent, an alcohol solvent, an aromatic solvent or an aliphatic solvent, more preferably an ester solvent, an aromatic solvent or an aliphatic solvent, and particularly preferably an ester solvent.
  • ester solvent examples include 2- (1-methoxy) propyl acetate, ethyl acetate, and ethyl lactate.
  • alcohol solvent examples include n-butanol and isobutanol.
  • aromatic solvent examples include benzene, toluene, xylene and the like.
  • aliphatic solvent examples include n-hexane and cyclohexane.
  • extraction solvent may be a pure solvent based on the above preferred solvent or a mixed solvent composed of a plurality of solvents.
  • the amount of the extraction solvent is not particularly limited as long as the organic particles can be extracted, but it is preferable that the amount of the extraction solvent is smaller than that of the organic particle dispersion in consideration of concentration and extraction.
  • the extraction solvent added is preferably in the range of 1 to: LOO, more preferably in the range of 10 to 90, and 20 to A range of 80 is particularly preferred. If it is too much, it will take a lot of time to concentrate, and if it is too little, extraction will be insufficient and the particles will be dispersed in the dispersion solvent. The child remains.
  • the temperature at which the extraction solvent is added and mixed is not particularly limited, but is preferably 1 to 100 ° C, more preferably 5 to 60 ° C. Any device may be used for adding and mixing the extraction solvent as long as each step can be preferably performed. For example, a separation funnel type device can be used.
  • filter filtration apparatus for example, an apparatus such as pressure filtration can be used.
  • Preferred filters include nanofilters and ultrafilters. It is preferable to remove the remaining dispersion solvent by filter filtration and further concentrate the organic particles in the concentrated extract to obtain a concentrated particle solution.
  • centrifuge used for concentration of organic particles by centrifugation may be any device as long as it can precipitate organic particles in an organic particle dispersion (or organic particle concentrated extract).
  • a centrifuge for example, in addition to a general-purpose device, one with a skimming function (function of sucking the supernatant layer during rotation and discharging it out of the system) or continuous centrifugation that continuously discharges solid matter.
  • Centrifugation conditions include centrifugal force (a value that represents the force at which centrifugal acceleration is multiplied by the gravitational acceleration) 50 ⁇ : LOOOO force preference ⁇ , 100 ⁇ 8000 force preference ⁇ , 150 ⁇ 6000 is especially preferred ⁇ .
  • the temperature at the time of centrifugation is a force depending on the solvent type of the dispersion liquid—preferably 10 to 80 ° C.—preferably 5 to 70 ° C. Particularly preferably 0 to 60 ° C.
  • the apparatus used for concentration of organic particles by drying under reduced pressure is not particularly limited as long as the solvent of the organic particle dispersion (or organic particle concentrated extract) can be evaporated.
  • a general-purpose vacuum dryer and a rotary pump a device capable of drying under heating and heating while stirring the liquid, and a device capable of continuous drying by passing the liquid through a heat-depressurized tube.
  • Heating vacuum drying temperature is preferably 30-230 ° C 35-200 ° C is more preferred 40-18 0 ° C force S Especially preferred ⁇ .
  • Pressure during decompression ⁇ 100-100,000 Pa force preferred ⁇ , 300-90000 Pa force more preferred, 500-80000 Pa force particularly preferred! / ,.
  • organic particles can be efficiently concentrated from the organic particle dispersion by combination with ultrafiltration or the above-described concentration method.
  • concentration factor for example, if the concentration of the particles in the organic particle dispersion as the raw material is 1, the concentration in the concentrated organic particle paste is preferably about 100 to 3000 times, more preferably about 500 to 2000 times. be able to.
  • ions unnecessary for the organic particle dispersion force can be removed.
  • the ions to be removed are not particularly limited, but it is preferable to remove ions having a low molecular weight such as sodium (Na), potassium (K), calcium (Ca), chlorine (C1) and the like.
  • the molecular weight is small and it is easy to move.
  • the total amount of ions after removal is preferably 1% by mass or less, more preferably 0.1% by mass or less, and particularly preferably 0.01% by mass or less, relative to the organic material.
  • fine dispersion means to increase the degree of dispersion by deaggregating particles in a dispersion.
  • the vehicle refers to a portion of a medium in which organic particles are dispersed in a liquid state, a portion that is liquid and hardens by acting with the organic particles (binder), and a component that dissolves and dilutes this (organic) Solvent).
  • the present invention it is preferable to perform redispersion in an organic solvent containing the above-described polymer compound or a polymer compound having an acidic group.
  • an organic compound is used as for the polymer compound or the polymer compound having an acidic group. It is preferable to add the same type or different type used during grain formation during redispersion. More preferred to add.
  • the organic particle concentration of the organic particle dispersion composition after redispersion is appropriately determined according to the purpose.
  • the organic particle concentration is 2 to 30% by mass with respect to the total amount of the dispersion composition. 4 to 20% by mass It is particularly preferable that the content is 5 to 15% by mass.
  • the amount of the binder and dissolved dilution component is appropriately determined depending on the type of the organic material, etc., but the binder is preferably 1 to 30% by mass with respect to the total amount of the organic particle dispersion composition, and is 3 to 20% by mass. It is particularly preferable that the content is 5 to 15% by mass.
  • the dissolution dilution component is preferably 5 to 80% by mass, more preferably 10 to 70% by mass.
  • organic particles are usually agglomerated due to concentration in a state where rapid filter filtration is possible.
  • Organic particles concentrated by centrifugation or drying are also aggregated by the concentration.
  • agglomerated organic particles are particles in which particles such as agglomerates are gathered by a secondary force
  • a dispersion method using ultrasonic waves or physical It is possible to use a method of adding energy.
  • the ultrasonic irradiation device preferably has a function capable of applying an ultrasonic wave of 10 kHz or higher, and examples thereof include an ultrasonic homogenizer and an ultrasonic cleaner.
  • the liquid temperature rises during ultrasonic irradiation, thermal aggregation of the particles occurs (see Pigment Dispersion Technology, Surface Treatment and Use of Dispersing Agents and Dispersibility Evaluation Technical Information Association 1999), so the liquid temperature is 1 to 100 ° C. 5-60 ° C is more preferable.
  • the temperature can be controlled by controlling the dispersion temperature, controlling the temperature of the temperature adjusting layer that controls the temperature of the dispersion, and the like.
  • the dispersing machine used to disperse the concentrated organic particles by applying physical energy. For example, kneaders, roll mills, atriders, super mills, dissolvers, homomixers, sand mills, etc. Examples include a disperser.
  • finely dispersed particles of redispersed organic particles (primary particles) can be obtained.
  • Japanese Patent Application Laid-Open No. 2004-43776 describes a method for obtaining fine particles with a small change in particle size after redispersion. When evaluated finely, a considerable amount (for example, about 0.1%) of particles exceeding 0.50 m is observed, which may cause a decrease in performance in a CCD color filter or the like.
  • This method includes a step of causing agglomeration rapidly in a poor solvent by adding an acid, and this is presumed to cause association of pigment particles.
  • the average particle size can be nanometer size, preferably 1 to 200 nm, more preferably 2 to 100 nm, and 5 to 50 nm. Is particularly preferred.
  • the Mv / Mn of the particles after redispersion is preferably 1.0 to 2.0, more preferably 1.0 to 1.8, and particularly preferably 1.0 to 1.5.
  • the organic particles are reconcentrated and reconstituted at the intended particle size, despite a nanometer size (for example, 10 to: LOOnm). Can be dispersed. For this reason, when an ink for inkjet is used, it is possible to obtain a clear ink having high optical density, excellent uniformity of the image surface, high saturation, and high clarity. Furthermore, when used in a color filter, the filter surface with high optical density is excellent in uniformity, the contrast is high, and image noise can be reduced.
  • a nanometer size for example, 10 to: LOOnm
  • the colored photosensitive resin composition of the present invention comprises at least (a) organic nanoparticles, (b) a binder, (c) a polyfunctional monomer (monomer or oligomer), and (d) a photopolymerization initiator or light. Includes a polymerization initiator system.
  • the method for producing organic nanoparticles has already been described in detail.
  • the content of the organic nanoparticles is 3 to 90% by mass with respect to the total solid content in the colored photosensitive resin composition (in the present invention, the total solid content refers to the total composition excluding the organic solvent). 20 to 80% by mass is more preferable and 25 to 60% by mass is more preferable. If this amount is too large, the viscosity of the dispersion increases, which may cause problems in production suitability. If the amount is too small, the coloring power is not sufficient.
  • the organic nanoparticles (pigment particles) functioning as a colorant preferably have a particle size of 0.1 ⁇ m or less, and particularly preferably a particle size of 0.08 m or less. Also in combination with ordinary pigments for toning Use it. As the pigment, those described above can be used.
  • the above-described polymer compound having a mass average molecular weight of 1000 or more can be preferably used as the binder in the colored photosensitive resin composition.
  • the content of the binder is generally 15 to 50% by mass, preferably 20 to 45% by mass, based on the total solid content of the colored photosensitive resin composition. If this amount is too large, the viscosity of the composition becomes too high, which causes a problem in production suitability. If the amount is too small, there is a problem in forming the coating film.
  • the polyfunctional monomer to be contained in the colored photosensitive resin composition of the present invention is preferably a polyfunctional monomer that has two or more ethylenically unsaturated double bonds and undergoes addition polymerization upon irradiation with light.
  • polyfunctional monomers include compounds having at least one addition-polymerizable ethylenically unsaturated group in the molecule and having a boiling point of 100 ° C. or higher at normal pressure.
  • Examples include monofunctional acrylates such as dipentaerythritol hexa (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate and phenoxychetyl (meth) acrylate, and monofunctional methacrylates.
  • monofunctional acrylates such as dipentaerythritol hexa (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate and phenoxychetyl (meth) acrylate, and monofunctional methacrylates.
  • Tacrylate Polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, trimethylol ethane triacrylate, trimethylol propane tri (meth) acrylate, trimethylol propane diatalate, neopentyl glycol di ( (Meth) atalylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hex (meth) acrylate, dipen Taerythritol Penta (meth) acrylate, hexanediol di (meth) acrylate, trimethylol propantri (atallylooxypropyl) ether, tri (atallylooxychetyl) isocyanurate, tri (atalylooxy) (Cetyl) cyanurate, glycerin tri (meth) at
  • urethane acrylates described in JP-B-48-41708, JP-B-50-6034 and JP-A-51-37193; JP-A-48-64183, JP-B 49-43191 and Japanese Patent Publication No. 52-30490 such as polyester acrylates; polyfunctional acrylates such as epoxy acrylates, which are reaction products of epoxy resin and (meth) acrylic acid; Metatalates can be mentioned.
  • trimethylolpropane tri (meth) acrylate pentaerythritol tetra (meth) acrylate, dipentaerythritol hex (meth) acrylate, and dipentaerythritol penta (meth) acrylate are preferred.
  • polymerizable compound B described in JP-A-11-133600 can also be mentioned as a preferable example.
  • These polyfunctional monomers are preferable.
  • Colored photosensitive resin compositions that can be used alone or in combination of two or more.
  • the content of the total solid content is generally 5 to 50% by mass, and preferably 10 to 40% by mass. If this amount is too large, it becomes difficult to control the developability, which causes a problem in production suitability. If the amount is too small, the curing power at the time of exposure will be insufficient.
  • Photopolymerization initiator or photopolymerization initiator system contained in the colored photosensitive resin composition of the present invention expresses the function of initiation of photopolymerization by a combination of a plurality of compounds.
  • polymerization initiator C described in JP-A-11-133600, or oxime-based 1-Ferru 1, 2-propanedione 1- (o ethoxycarbol) ) Oxim, O Benzyl-4,-(Benzmercapto) Benzyl Hexyl-Ketoxime, 2, 4, 6 Trimethylphenol-Lulphyl-Folphosphate Oxide, Hexafluorophospho-Trialkylphenol Phospho- Umu salt and the like can also be mentioned as suitable.
  • photopolymerization initiators or photopolymerization initiator systems may be used singly or as a mixture of two or more, but it is particularly preferable to use two or more. When at least two types of photopolymerization initiators are used, display characteristics, particularly display unevenness, can be reduced.
  • the content of the photopolymerization initiator or photopolymerization initiator system with respect to the total solid content of the colored photosensitive resin composition is generally 0.5 to 20% by mass, and preferably 1 to 15% by mass. If this amount is too large, the sensitivity becomes too high and control becomes difficult. If it is too low, the exposure sensitivity will be too low.
  • an organic solvent may be used in addition to the above components.
  • organic solvents include, but are not limited to, esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate.
  • Alkyl esters methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 3-oxypropion Alkyl 3-alkylpropionates such as methyl 3-ethylpropionate; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxypropionate, 2 Methyl oxypropionate 2 Okishipuropio phosphate Echiru, 2 Okishipuropion propyl, 2-methyl methoxypropionate, 2- Ethyl methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, 2-ethyl ethoxy
  • methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, solvate acetate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate, 2 heptanone, cyclohexanone, ethyl carbitol Acetate, butyl carbitol acetate, propylene glycol methyl ether acetate and the like are preferably used as the solvent in the present invention.
  • These solvents may be used alone or in combination of two or more.
  • a solvent having a boiling point of 180 ° C. to 250 ° C. may be used as necessary. Examples of these high boiling point solvents are as follows.
  • Diethylene glycol monobutyl ester diethylene glycol monoethyl enoate acetate, diethylene glycol monoethyl ether, 3, 5, 5 trimethyl-2-cyclohexene 1-one, butyl lactate, dipropylene glycol monomethenoylate
  • the content of the solvent is preferably 10 to 95% by mass with respect to the total amount of the resin composition.
  • the color filters that have been used in the past have a problem that the color of each pixel becomes darker in order to achieve high color purity, and the uneven power of the pixel film thickness is recognized as color unevenness as it is. . For this reason, it has been demanded to improve the film thickness fluctuation when forming (coating) the photosensitive resin layer, which directly affects the film thickness of the pixel.
  • the color filter of the present invention or the photosensitive resin transfer material of the present invention can be controlled to have a uniform film thickness, and from the viewpoint of effectively preventing coating unevenness (color unevenness due to film thickness variation), It is preferable to include an appropriate surfactant in the greave composition.
  • the surfactant include those disclosed in JP-A-2003-337424 and JP-A-11-133600.
  • the content of the surfactant is preferably 5% by mass or less based on the total amount of the resin composition.
  • the colored photosensitive resin composition of the present invention preferably contains a thermal polymerization inhibitor.
  • the thermal polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, p-methoxy fenenore, di-t-butinole p-crezo-monore, pyrogalonore, tert-tinole teconole, benzoquinone, 4, 4'-thiobis (3-methyl-6 — T-Butylphenol), 2,2, -Methylenebis (4-methyl-6-t-butylphenol), 2-Mercaptobens imidazole, and Funothiazine.
  • the content of the thermal polymerization inhibitor is preferably 1% by mass or less based on the total amount of the resin composition.
  • a colorant in addition to the colorant (pigment), a colorant (dye or pigment) can be added to the colored photosensitive resin composition of the present invention as necessary.
  • a pigment among the colorants it is desirable that the pigment is uniformly dispersed in the colored photosensitive resin composition, so that the particle size is 0.1 ⁇ m or less, particularly 0.0 ⁇ m or less. It is preferable that
  • the dye or pigment include the colorant described in JP-A-2005-17716, [0038]-[0040], and JP-A-2005-361447 [0068]-[0]. [072] and the colorants described in JP-A-2005-17521, [0080] to [0088] can be suitably used.
  • the auxiliary dye or pigment content is preferably 5% by weight or less, based on the total amount of the resin composition.
  • the colored photosensitive resin composition of the present invention can contain an ultraviolet absorber as necessary.
  • the ultraviolet absorber include salicylate-based, benzophenone-based, benzotriazole-based, cyanoacrylate-based, -chelate-chelated, and hindered amine-based compounds in addition to the compounds described in JP-A-5-72724.
  • ferric salicylate 4 t-butyl ferric salicylate, 2,4-di-t-butyl ferrule 3 ', 5'-di-t-4'-hydroxybenzoate, 4-t-butyl fuel Salicylate, 2,4-Dihydroxybenzophenone, 2 Hydroxy-4-methoxybenzophenone, 2 Hydroxy 4-n-Otoxybenzophenone, 2 -— (2′-Hydroxy-5′-methylphenyl) benzotriazole, 2 -— (2 '—Hydroxy 3' t-butyl-5, 1-methylphenol) 5 Chronobenzozoazole, Ethyl 2 Cyan 3, 3—Diphenyl acrylate, 2, 2, 1-hydroxy 4-methoxybenzophenone, Nickel dibutyl Dithiocarbamate, bis (2, 2, 6, 6-tetramethyl-4-pyridine) sebacate, 4 t-butylphenol salicylate, salicylate, 4-hydroxy 2, 2, 6, 6-tetramethyl
  • the colored photosensitive resin composition of the present invention contains "adhesion aid" described in JP-A-11-133600, other additives and the like in addition to the above-mentioned additives. It can be made.
  • the components contained in the coating film using the colored photosensitive resin composition of the present invention are the same as those already described in the section of [Colored photosensitive resin composition].
  • this departure The thickness of the coating film using the bright colored photosensitive resin composition can be determined as appropriate according to the application force S capable of being S, 0.5-5.O / zm force S, preferably 1. It is more preferably 0 to 3.0 m than force S.
  • a monomer or oligomer contained therein is polymerized to form a colored photosensitive resin composition polymer film, and a color filter having the same (The production of the color filter will be described later.)
  • O Polymerization of the polymerizable monomer or polymerizable oligomer is effected by (d) photopolymerization initiator or photopolymerization initiator system by light irradiation. Can be done.
  • the coating film can be formed by applying a colored photosensitive resin composition by a normal coating method and drying, but in the present invention, a slit-like hole is formed in a portion from which the liquid is discharged. It is preferable to apply with a slit-shaped nozzle.
  • JP-A-2004-89851, JP-A-2004-17043, JP-A-2003-170098, JP-A-2003-164787, JP-A-2003-10767, JP-A-2002-7 Slit nozzles and slit coaters described in 9163, JP 2001-310147, and the like are preferably used.
  • the coating method of the colored photosensitive resin composition on the substrate is superior in spin coating because it can uniformly and precisely coat a thin film of 1 to 3 ⁇ m, and is widely used for the production of color filters. Can be used generally.
  • slit coating suitable for coating a substrate that is wider and larger than spin coating has been developed in order to increase manufacturing efficiency and manufacturing cost. It has come to be used for the production of filters. From the viewpoint of liquid-saving properties, slit coating is superior to spin coating, and a uniform coating film can be obtained with a smaller amount of coating liquid.
  • a coating head having a slit (gap) with a width of several tens of microns at the tip and a length corresponding to the coating width of a rectangular substrate is used, and the clearance (gap) with the substrate is several tens to several hundreds.
  • This slit coating is (1) less liquid loss than spin coating, (2) no coating liquid jumping, reducing the cleaning process, and (3) respraying scattered liquid components to the coating film.
  • slit coating is suitable for producing color filters for large-screen liquid crystal display devices, and is expected to be an advantageous coating method for reducing the amount of coating liquid.
  • slit coating forms a coating film with a much larger area than spin coating, a wide slit exit force When discharging coating liquid, a certain degree of relative speed is applied between the coater and the object to be coated. Need to keep. For this reason, good fluidity is required for the coating solution used in the slit coating method.
  • the slit coating is particularly required to keep the conditions of the coating solution supplied to the substrate from the slit of the coating head constant over the entire coating width. If the liquid properties such as fluidity and viscoelastic properties of the coating liquid are insufficient, uneven coating will occur and it will be difficult to keep the coating thickness constant in the coating width direction, and a uniform coating film will be obtained. I can't do that!
  • the photosensitive transfer material of the present invention is preferably formed using a photosensitive resin transfer material described in JP-A-5-72724, that is, an integrated film.
  • a photosensitive resin transfer material described in JP-A-5-72724, that is, an integrated film.
  • the constitution of the body-type film include a constitution in which the temporary support Z, the thermoplastic resin layer Z, the intermediate layer Z, the photosensitive resin layer Z, and the protective film are laminated in this order, and the photosensitive transfer of the present invention.
  • a photosensitive photosensitive resin is provided by using the above-described colored photosensitive resin composition of the present invention.
  • the temporary support is flexible and can be marked even under pressure, or even under pressure and heating! /, Deformation, shrinkage or elongation. Does not occur It is necessary.
  • Examples of such a temporary support include polyethylene terephthalate film, cellulose triacetate film, polystyrene film, polycarbonate film and the like, and among them, biaxially stretched polyethylene terephthalate film is particularly preferable.
  • an organic polymer substance described in JP-A-5-72724 is preferred as a component used for the thermoplastic resin layer.
  • the Vicat method specifically, the American Material Testing Method, Est. It is particularly preferred that the polymer is selected from organic polymer materials having a soft softening point measured by ASTM D1235 of about 80 ° C. or less.
  • polyolefins such as polyethylene and polypropylene, ethylene copolymers such as ethylene and butyl acetate or saponified products thereof, ethylene and acrylic acid esters or saponified products thereof, polyvinyl chloride, and vinyl chloride.
  • Salt-vinyl copolymer such as butyl acetate and its ken hydrate, poly-salt vinylidene, vinylidene chloride copolymer, polystyrene, styrene and (meth) acrylic acid ester or saponified product thereof Styrene copolymer, polytoluene toluene, vinyl toluene and (meth) acrylic acid ester or saponified butyltoluene copolymer, poly (meth) acrylic acid ester, (meth) acrylic acid butyl and vinyl acetate
  • organic polymers such as polyamide resin such as dimethyl methyl nylon and N-dimethylaminolated nylon.
  • an intermediate layer for the purpose of preventing mixing of components during application of a plurality of application layers and during storage after application.
  • an oxygen-blocking film having an oxygen-blocking function described in JP-A-5-72724 as a “separation layer”. The time load of the exposure machine is reduced and the productivity is improved.
  • oxygen-blocking membrane As the oxygen-blocking membrane, a normal medium force that exhibits low oxygen permeability and is preferably dispersed or dissolved in water or an aqueous alkali solution can be appropriately selected. Of these, the combination of polybulal alcohol and polybulurpyrrolidone is particularly preferred. It is.
  • the protective film may be made of the same or similar material as the temporary support, but it must be easily separated from the photosensitive resin layer.
  • silicone paper, polyolefin, or polytetrafluoroethylene sheet is suitable as the protective film material.
  • the photosensitive transfer material of the present invention is obtained by applying a coating solution in which an additive for a thermoplastic resin layer is dissolved on a temporary support (a coating solution for a thermoplastic resin layer) and drying the thermoplastic resin layer. After that, a solution of an intermediate layer material that also has solvent power is applied and dried on the thermoplastic resin layer without dissolving the thermoplastic resin layer, and then the photosensitive resin layer is coated with a solvent that does not dissolve the intermediate layer. It can be prepared by coating and drying.
  • thermoplastic resin layer and the intermediate layer on the temporary support and a sheet provided with the photosensitive resin layer on the protective film are prepared, and the intermediate layer and the photosensitive resin layer are in contact with each other.
  • a sheet provided with a thermoplastic resin layer on the temporary support, and a photosensitive resin layer and an intermediate layer were provided on a protective film. It can also be produced by preparing a sheet and bonding them together so that the thermoplastic resin layer and the intermediate layer are in contact with each other.
  • the thickness of the photosensitive resin layer is preferably 1.0 to 5. ⁇ m force, more preferably 1.0 to 4. O / zm force. 0 ⁇ 3.0 m force ⁇ Especially preferred! / ⁇ . Further, although not particularly limited, the preferred film thickness of each of the other layers is as follows: Temporary support 15 to: LOO / zm Also 0.5-3. O / zm, protective film 4-40 m force is generally preferred.
  • the coating in the above production method can be performed by a normal coating apparatus or the like.
  • the coating is preferably performed by the coating apparatus (slit coater) using the slit-like nozzle already described in the section of [Coating film of colored photosensitive resin composition].
  • the coating apparatus slit coater
  • Preferred specific examples of the slit coater are the same as described above.
  • contrast refers to the ratio of the amount of transmitted light between two polarizing plates when the polarization axis is parallel and when it is vertical (“1990 7th Color Optical Conference, 512 color display 10 See 4 "size TFT — color filters for LCD, Ueki, Koseki, Fukunaga, Yamanaka” etc.
  • the high contrast of the color filter means that the brightness and darkness discrimination when combined with the liquid crystal can be increased. This is a very important performance in order to replace the liquid crystal display with a CRT.
  • the chromaticity power of each single color of red (R), green (G), and blue (B) by the F10 light source is as described in the table below.
  • the difference ( ⁇ E) from the value (hereinafter referred to as “target chromaticity” in the present invention) is preferably within a range of 5 or less, and more preferably 3 or less. It is particularly preferable that the number is within 2.
  • the chromaticity is measured with a microspectrophotometer (manufactured by Olympus Optical Co., Ltd .; OSP100 or 200), calculated as a result of F10 light source field of view of 2 degrees, and expressed as an xyY value in the xyz color system.
  • the difference from the target chromaticity is expressed by the color difference of the La * b * color system.
  • the color filter of the present invention can be produced by a method such as a method in which a photosensitive resin layer is formed on a substrate, and exposure and development are repeated for the number of colors. If necessary, the boundary may be divided by a black matrix.
  • an ordinary coating apparatus can be used for coating the colored photosensitive resin composition, but among others, already [coated film of colored photosensitive resin composition]
  • the slit coater described in the section can be preferably used. Preferred examples of the slit coater are the same as described above.
  • the film thickness is preferably 1.0 to 3. O / zm, more preferably 1.0 to 2.5 / zm, 1.5 to 2.5 5 111 especially preferred 1 ⁇ 0
  • a photosensitive resin layer formed into a film is pressure-bonded or heat-pressed with a roller or flat plate heated and Z or pressurized on a substrate described later.
  • Specific examples include laminators and laminating methods described in JP-A-7-110575, JP-A-11-77942, JP-A-2000-334836, and JP-A-2002-148794. From this point of view, it is preferable to use the method described in JP-A-7-110575.
  • the preferable film thickness is the preferred U film thickness described in the section of [Photosensitive resin transfer material]. It is the same.
  • the substrate on which the color filter is formed for example, a transparent substrate is used, and a known soda glass plate, low expansion glass, non-alkaline glass, quartz glass plate, etc., having an acid silicon film on the surface. Glass plate or plastic film.
  • substrate can make favorable adhesion
  • a method described in JP-A-2000-39033 is preferably used.
  • the film thickness of the substrate is generally preferably 700 to 1200 / ⁇ ⁇ , and 500 to: L 100 m force is particularly preferable! / ⁇ . [0281] (Oxygen barrier membrane)
  • an oxygen-blocking film can be further provided on the photosensitive resin layer.
  • the oxygen-blocking film include those already described in the section (intermediate layer) of [Photosensitive resin transfer material].
  • the thickness of the oxygen blocking film is generally preferably 0.5 to 3. ⁇ m.
  • a predetermined mask is disposed above the photosensitive resin layer formed on the substrate, and then the mask upward force is also exposed through the mask, the thermoplastic resin layer, and the intermediate layer, and then development with a developer is performed. It is possible to obtain the color filter of the present invention by repeating the process of performing as many times as the number of colors.
  • the light source for the exposure can be appropriately selected and used as long as it can irradiate light in a wavelength region capable of curing the photosensitive resin layer (for example, 365 nm, 405 nm, etc.).
  • a wavelength region capable of curing the photosensitive resin layer for example, 365 nm, 405 nm, etc.
  • an ultrahigh pressure mercury lamp, a high pressure mercury lamp, a metal halide lamp, etc. are mentioned.
  • the amount of exposure is usually about 5 to 200 mjZcm 2 , preferably 10 to about LOOmjZcm 2 .
  • the developer a normal developer such as that described in JP-A-5-72724, which is not particularly limited, can be used.
  • the developer has a developing behavior in which the photosensitive resin layer is dissolved.
  • a developer containing 1 ⁇ & 7 to 13 in a concentration of 0. O5 to 5mo 1ZL.
  • a small amount of an organic solvent miscible with water may be added.
  • organic solvents that are miscible with water include methanol, ethanol, 2-propanol, 1 propanol, butanol, diacetone alcohol, ethylene glycol monomethino ethenole, ethylene glycol monomethino enotenole, and ethylene glycol monomethanol.
  • the concentration of the organic solvent is preferably 0.1% by mass to 30% by mass.
  • a normal surfactant can be further added to the developer.
  • concentration of the surfactant is preferably 0.01% by mass to 10% by mass.
  • development method methods such as paddle development, shower development, shower & spin development, and dip imaging can be used.
  • the uncured portion can be removed by spraying a developer onto the photosensitive resin layer after exposure.
  • a developer onto the photosensitive resin layer after exposure.
  • the developer temperature is preferably 20 ° C to 40 ° C, and the developer pH is preferably 8 to 13.
  • a colored photosensitive resin composition that forms a color filter is stacked. From the viewpoint of cost reduction, it is preferable to form a base, form a transparent electrode on it, and then form a spacer by overlapping projections for split orientation.
  • the film thickness becomes thinner each time it is stacked due to the leveling of the coating solution. For this reason, it is preferable to overlap the four colors K (black) 'R'G'B, and further overlap the divisional alignment protrusions.
  • the thickness is kept constant, so that the overlapping color is preferably 3 or 2 colors.
  • the size of the base is preferably 25 m or more and particularly preferably 30 m or more from the viewpoint of preventing deformation of the photosensitive resin layer when the transfer material is laminated and maintaining a constant thickness. .
  • the CCD device of the present invention is manufactured using the pigment nanoparticles obtained by the production method of the present invention.
  • the manufactured color filter is provided.
  • the CCD device of the present invention will be described in detail.
  • the alkali-soluble resin used in the CCD device is preferably a linear organic polymer, soluble in an organic solvent, and developable with a weak alkaline aqueous solution.
  • linear organic high molecular polymers include polymers having a carboxylic acid in the side chain, such as JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54- Nos.
  • methacrylic acid copolymer examples include maleic acid copolymers, partially esterified maleic acid copolymers, and acidic cellulose derivatives having a carboxylic acid in the side chain.
  • a polymer obtained by adding an acid anhydride to a polymer having a hydroxyl group is also useful.
  • benzyl (meth) atarylate Z (meth) acrylic acid copolymer and benzyl (meth) atarylate Z (meth) acrylic acid / and multi-component copolymers with other monomers are particularly suitable.
  • Other useful water-soluble polymers include 2-hydroxyethyl methacrylate, polybutyl pyrrolidone, polyethylene oxide, and polybutyl alcohol.
  • the polymerizable monomer is preferably a compound having at least one addition-polymerizable ethylene group and having an ethylenically unsaturated group having a boiling point of 100 ° C. or higher under normal pressure. That's right.
  • Compounds having at least one addition-polymerizable ethylenically unsaturated group and a boiling point of 100 ° C or higher at normal pressure include polyethylene glycol mono (meth) acrylate and polypropylene glycol mono (meth) acrylate.
  • Monofunctional acrylates and meta acrylates such as phenoxychetyl (meth) acrylate, polyethylene glycol di (meth) acrylate, trimethylol ethane tri (meth) acrylate, neopentyl glycol di (meth) acrylate, penta erythritol tri (Meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexanediol (meth) acrylate, trimethylolpropane tri (atalylooxypropyl) ether, toluene (Meth) atelar toy after adding ethylene oxide or propylene oxide to polyfunctional alcohols such as isocyanurate, glycerin and trimethylolethane
  • a compound represented by the following general formula (B-1) or (B-2) can also be used.
  • B is each independently one (CH CH O)-and one (CH CH (
  • CH)) ⁇ ) — represents one of the following: X represents each independently an taliloyl group, a methacryloyl group, and
  • the total of the allyloyl group and the metathalyl group is 5 or 6, and that in the formula (B-2) is 3 or 4 N represents an integer of 0 to 6 each independently, and the sum of each force n is 3 to 24; m represents an integer of 0 to 6 each independently, and the force represents each m
  • the total is 2-16.
  • These polymerizable monomers can be used in any ratio as long as they can form a coating film having adhesiveness upon irradiation with radiation.
  • the amount used is usually 5 to 90% by mass, preferably 10 to 50% by mass, based on the total solid content of the composition.
  • colorant various conventionally known dyes, inorganic pigments or organic pigments can be used singly or in combination.
  • dye known dyes for conventional color filters can be used without any particular limitation.
  • dye currently disclosed by the gazette etc. can be used.
  • the chemical structure is pyrazole azo, lino azo, triphenyl methane, anthraquinone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine. Etc. can be used.
  • the curable composition can be cured at a relatively low temperature, even a dye that is inferior in heat resistance compared to a pigment has a high temperature during post-beta to impart durability to the cured film. It is possible to reduce problems such as decomposition even when exposed to water.
  • the inorganic pigment is a metal compound represented by a metal oxide, a metal complex salt, or the like, and specifically iron, conoleto, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony.
  • Metal oxides such as the above, and complex oxides of the above metals.
  • Organic pigments include CI Pigment Yellow 11, 24, 31, 53, 83, 8 5, 99, 108, 109, 110, 138, 139, 150, 151, 154, 167, 18 5, CI Pigment Orange 36, 38, 43, 71, CI Pigment Red 1 05, 122, 149, 150, 155, 171, 175, 176, 177, 209, 224, 242, 254, CI Pigment Violet 19, 23, 32, 39, CI Pigmen t Blue 1, 2, 15, 16, 22, 60, 66, 15: 3, 15: 6, CI Pigmen t Green 7, 36, 37, CI Pigment Brown 25, 28, CI Pigment Black 1, 7, carbon Black etc. can be mentioned.
  • red pigment an anthraquinone pigment, a perylene pigment alone or a mixture of at least one of them with a disazo yellow pigment or an isoindoline yellow pigment is used.
  • CI pigment red 177 is used as an anthraquinone pigment
  • CI pigment red 155 is used as a perylene pigment.
  • Mixing with CI pigment yellow 83 or CI pigment yellow 139 is preferable in terms of color reproducibility. It is.
  • the mass ratio of red pigment to yellow pigment is good from 100: 5 to 100: 50. Within this range, it is preferable because the light transmittance of 400 nm to 500 nm can be suppressed and the color purity can be increased.
  • the green pigment a halogenated phthalocyanine pigment alone or a mixture of a disazo yellow pigment, a quinophthalone yellow dye or an isoindoline yellow pigment is used.
  • CI Pigment Green 7, 36 37 and CI Pigment Yellow 83, 138, 139 are preferred.
  • the mass ratio of the green pigment to the yellow pigment is preferably from 100: 5 to L00: 100. Within this range, the light transmittance from 400 nm to 450 nm can be suppressed and good color purity can be obtained.
  • the blue pigment a phthalocyanine pigment alone or a mixture with a dioxazine purple pigment is used.
  • CI pigment blue 15: 6 and CI pigment violet 23 are preferably mixed.
  • the mass ratio of blue pigment to purple pigment is preferably 100: 0 to 100: 50. Within this range, the light transmittance from 400 nm to 420 nm can be suppressed and the color purity can be increased. Togashi.
  • pigment for the black matrix carbon, titanium oxide, iron oxide, alone or a mixture thereof is used, and carbon and titanium oxide are preferable. Mass ratio from 100: 5
  • a range of 100: 40 is preferred. Within this range, the light transmittance at long wavelengths is small and the dispersion stability is also good.
  • Solvents include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate.
  • Ethyl lactate methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, 3-oxy Alkyl esters of 3-oxypropionic acid such as ethyl propionate; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl ethoxypropionate, ethyl ethoxypropionate, methyl 2-oxypropionate, 2 —Oxypropionate 2-propylpropionate, 2-methoxymethyl propionate, 2-methoxypropionate, 2-methoxypropionate, 2-methoxypropylpropionate, 2-ethoxypropionate, 2-ethoxypropionate, 2-oxypropionate 2-methyl methyl propionate, 2-oxy-2-e
  • methyl ethoxypropionate, 3 ethyl ethoxypropionate, ethyl solvate sorb acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 heptanone, cyclohexanone, Ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate and the like are preferably used.
  • the amount of the solvent added is usually 60 to 90% by mass, preferably 70 to 90% by mass in the composition.
  • a sensitizer can be used in combination.
  • Specific examples include 9 fluorenone, 2 chloro 9 fluorenone, 2-methyl 9 fluorenone, 9 anthrone, 2 bromo 9 —anthrone, 2 ethyl 9 anthrone, 9, 10 anthraquinone, 2 ethyl 9, 10 anthraquinone, 2— t-butyl-9,10 anthraquinone, 2,6 dichloro-9,10-anthraquinone, benzyl, dibenzalacetone, p- (dimethylamino) phenol ketol, P- (dimethylamino) phenol ⁇ -methylstyryl ketone, benzo Anthrone and the like include benzothiazole compounds described in JP-B 51-48516.
  • a general manufacturing method of a color filter used in a CCD device is as follows. A step of applying and drying the composition (color resist solution) of the present invention on a substrate, a step of pattern exposure of the obtained dry coating film with an i-line stepper, a step of alkali development after exposure, and a heat treatment A color filter is obtained by sequentially performing the steps and repeating the above steps for each color (three or four colors) to produce a cured film.
  • the curable composition is generally dried on a suitable substrate with a spinner or the like so that the film thickness when dried is generally 0.1 to 5111, preferably 0.2 to Apply to 2 m and leave in oven at 85 ° C for 2 minutes to obtain a smooth coating.
  • the substrate is not particularly limited, but it is a substrate for electronic parts such as a glass plate, a plastic plate, an aluminum plate, a silicon wafer for an imaging element, and further a transparent resin plate, a resin film, a brush.
  • Duct tube display surface light-sensitive surface for image sensing, wafers with solid-state image sensors such as CCD, BBD, CID, BASIS, contact image sensor using thin film semiconductors, liquid crystal display surface, color electrophotographic photosensitive Body, Electrum Chromy (EC) display substrate.
  • a pattern of the curable composition is formed after thinly coating with a silane coupling agent or the like on the substrate in advance, or in some cases, a silane coupling agent is previously contained in the curable composition.
  • a flattening film for eliminating the step and smoothing the coating surface is applied on the substrate, and then the curable composition of the present invention is applied.
  • an image sensor such as a CCD is composed of a photoelectric conversion unit (photodiode) that generates electrons on a silicon substrate according to the amount of light received, and a readout gate unit that outputs the generated electrons. If the gate is exposed to light, it will cause noise and accurate data will not be output.Therefore, a light-shielding film layer is formed on the top of the readout gate, and there is a step between the photodiode part without the light-shielding film layer. May have occurred.
  • the optical path length becomes long, so that the image becomes dark and the light condensing property becomes poor.
  • the material for the flat film include a photo-curable resist solution as in the present invention, thermosetting resins such as acrylic and epoxy resins, and the like.
  • the solvent is evaporated and a normal baking is performed to obtain a dry coating film.
  • This prebeta method includes drying under reduced pressure, indirect hot heat drying with high-temperature air, etc., and direct heat drying (about 80 to 140 ° C, 50 to 200 seconds) with a hot plate.
  • post-beta is performed in order to sufficiently cure the pattern obtained after development to increase the mechanical strength and form a permanent film.
  • the first formed pattern is then subjected to application, exposure and development of another color resist solution twice. In this case, pattern loss due to color mixing, exposure, and development with the applied resist solution Post-beta is performed so as not to occur.
  • This post-beta is used in the same way as pre-beta, but at a higher temperature and longer time than pre-beta conditions.
  • indirect heating by oven is performed at about 180 to 250 ° C. for about 0.5 to 2 hours
  • direct heating by hot plate is performed at about 180 to 250 ° C. for about 2 to 10 minutes.
  • the light source for exposure is not particularly limited, i-line of a mercury lamp can be cited as a light source that has a significant effect on pattern formation.
  • the feature of the present invention is an appropriate surface power of the process. The feature is particularly remarkable in the production of a color filter for an image sensor using i-line, which is one of the line spectrum of a mercury lamp, but it is also used for an LCD. Of course, it can be used.
  • the developer used for the development of the curable composition is not particularly limited, and a conventionally known developer can be used. Among them, an organic alkaline developer of a quaternary ammonium salt such as tetramethyl ammonium hydroxide (TMAH) is preferable for achieving the object of the present invention.
  • TMAH tetramethyl ammonium hydroxide
  • a normal photopolymerization initiator can be used as the polymerization initiator.
  • the vicinal polykettle aldo two Louis compound described in US Pat. No. 2,367,660, US Pat. Nos. 2,367,661 and 2,367,670 Substituted with the ⁇ -hydrocarbon described in US Pat. No. 2,722,512, the acylo ether described in US Pat. No. 2,448,828.
  • the content of the photopolymerization initiator (including the above-mentioned ordinary photopolymerization initiator) in the dye-containing negative curable composition is 0 with respect to the solid content (mass) of the radical polymerizable monomer. 0 1 to 50% by weight is preferred 1 to 30% by weight is more preferred 1 to 20% by weight is particularly preferred. When the content is in the above range, sufficient polymerization and curing can be performed, and polymerization is difficult to proceed. In addition, the polymerization rate increases but the molecular weight does not decrease and the film strength does not decrease.
  • a sensitizer or a light stabilizer can be used in combination with the photopolymerization initiator.
  • benzoin benzoin methyl ether, 9 fluorenone, 2 chloro 9 fluorenone, 2—methyl 9 fluorenone, 9 anthrone, 2 bromo 9 —anthrone, 2 ethyl 9 anthrone, 9, 10 anthraquinone, 2 ethyl 9, 1 0 Anthraquinone, 2-t-butyl-9, 10 Anthraquinone, 2, 6 Dichloro-9, 10 Anthraquinone, Xanthone, 2-Methylxanthone, 2-Methoxyxanthone, 2-Ethoxyxanthone, Thioxanthone, 2, 4 Jetylthioxanthone, Atalidone 10 butyl 2 -chloroataridon, benzyl, dibenzalacetone, p- (dimethylamino) phenol styryl ketone, p- (dimethylamino) phenol-p-methylstyryl
  • the liquid crystal display device of the present invention uses the color filter of the present invention having excellent contrast and is excellent in descriptive power such as black spots.
  • the color filter of the present invention is preferably a VA system. It can also be suitably used as a large screen liquid crystal display device such as a notebook personal computer display or a television monitor.
  • the color filter of the present invention can be used for a CCD device and exhibits excellent performance.
  • Another preferred embodiment of the present invention includes the following examples.
  • a method for producing an organic particle dispersion composition comprising producing a material as organic particles and concentrating the material, by concentrating the dispersion containing the organic particles by ultrafiltration.
  • the organic material is an organic pigment, wherein (A) to (C) The manufacturing method of the organic-particle dispersion composition of description.
  • a pigment solution was prepared by dissolving 0.6 g of Pigment (Vigment Red 254) in a solution prepared by mixing 1-methyl-2-pyrrolidone and ImolZL-sodium hydroxide aqueous solution 6: 1 to 15 mmol, L. Also, methacrylic acid / benzyl methacrylate copolymer 0.75 g (molar ratio 28/72, mass average molecular weight: 30,000, 40% 1-methoxy-2-propyl acetate solution), pigment dispersant A 0.3 g, dispersant Polybulpyrrolidone 0.6 g (manufactured by Wako Pure Chemical Industries, Ltd., K30, molecular weight 40,000) was dissolved in the above solution. Separately from this, water was prepared as a poor solvent.
  • the temperature of the solution was controlled at 25 ° C, and the pigment solution was added to 1000 ml of poor solvent water stirred at 500 rpm with a GK-0222-10 type ramond stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd., manufactured by Nippon Seimitsu Chemical Co., Ltd.
  • An organic pigment particle dispersion was prepared by injecting 22 Oml at a flow rate of 50 mlZmin using an NP-KX-500 large capacity non-pulsating pump.
  • the prepared organic particle dispersion was measured using Nanotrac UPA-EX150 manufactured by Nikkiso Co., Ltd., and the particle size and monodispersity were evaluated. The number average particle size was 32 nm and MvZMnl.35.
  • the prepared organic pigment particle dispersion (pigment particle concentration of about 0.05% by mass) was desalted and concentrated using CIO-TZRUM-2, an ultrafiltration machine manufactured by Nitto Denko. The conditions were as follows: liquid flow rate lL / min, liquid feed pressure 0.2 MPa, ultrafiltration filter molecular weight cut off 500,000. As a result, 400 ml of an organic pigment particle dispersion (pigment particle concentration: about 1.5% by mass) was obtained.
  • the concentrated extract from which organic pigment particles have been extracted is filtered using a FP-010 filter manufactured by Sumitomo Electric Fine Polymer Co., Ltd. The amount 0/0) was obtained. At this time, the sodium (Na) ion concentration was 0.01% by mass with respect to the pigment.
  • the pigment composition having the above composition was dispersed with a motor mill M-50 (manufactured by Eiger) at a peripheral speed of 9 m / s using Zirco Your beads having a diameter of 0.65 mm.
  • the pigment composition thus prepared was measured as a pigment dispersion composition A using Nanotrack UPA-EX150 manufactured by Nikkiso Co., Ltd., and the particle size and monodispersity were evaluated.
  • Pigment Dispersion Composition A the methacrylic acid / benzyl methacrylate copolymer used for preparing Pigment Dispersion Composition A using the paste was replaced with methacrylic acid / benzyl methacrylate / styrene copolymer 15 Pigment dispersion composition as in Pigment dispersion composition A, except that 8 g (molar ratio 27:60:13, mass average molecular weight: 28,000, 40% 1-methoxy-2-propyl acetate solution) was used.
  • Object B was made.
  • Pigment Dispersion Composition A 15.8 g (weight average) of the methacrylic acid / benzyl methacrylate copolymer used in preparing Pigment Dispersion Composition A using the paste was used.
  • Pigment Dispersion Composition C was prepared in the same manner as Pigment Dispersion Composition A, except that the average molecular weight was 33,000 and a 40% 1-methoxy-2-propyl acetate solution was used.
  • Pigment dispersion composition B was the same as pigment dispersion composition B except that the methacrylic acid / benzyl methacrylate copolymer used in preparing the organic pigment particle dispersion was used. D was produced.
  • Pigment Dispersion Composition B instead of using the methacrylic acid / benzyl methacrylate copolymer used in preparing the organic pigment particle dispersion, 0.75 g of methacrylic acid / benzyl methacrylate copolymer was dispersed in the pigment.
  • Pigment dispersion composition E was prepared in the same manner as pigment dispersion composition B, except that it was added during preparation of the composition.
  • An organic pigment particle dispersion was prepared in the same manner as in Example 1.
  • the obtained pigment dispersion compositions A to F were each applied onto a glass substrate so as to have a thickness of 2 ⁇ m, thereby preparing samples. This sample was observed with an optical microscope, and the number of particles with a diameter of 0.5 ⁇ m or more (coarse particle number) at 1 mm 2 was evaluated.
  • the particle size and particle size distribution MvZMn are shown in Table 1.
  • a pigment solution was prepared by dissolving 0.6 g of Pigment (Vigment Red 254) in a solution prepared by mixing 1-methyl-2-pyrrolidone and ImolZL-sodium hydroxide aqueous solution 6: 1 to 15 mmol, L. Also, methacrylic acid / benzyl methacrylate copolymer 0.75 g (molar ratio 28/72, mass average molecular weight: 30,000, 40% 1-methoxy-2-propyl acetate solution), pigment dispersant A 0.3 g, dispersant Polybulpyrrolidone 0.6 g (manufactured by Wako Pure Chemical Industries, Ltd., K30, molecular weight 40,000) was dissolved in the above solution. Separately from this, water was prepared as a poor solvent.
  • the temperature was controlled at 25 ° C, and the pigment solution was added to 1000 ml of poor solvent water stirred at 500 rpm with a GK-0222-10 type ramond stirrer manufactured by Fujisawa Pharmaceutical Co., Ltd., manufactured by Nippon Seimitsu Chemical Co., Ltd.
  • An organic pigment particle dispersion was prepared by injecting 22 Oml at a flow rate of 50 mlZmin using an NP-KX-500 large capacity non-pulsating pump.
  • the prepared organic particle dispersion was measured using Nanotrac UPA-EX150 manufactured by Nikkiso Co., Ltd., and the particle size and monodispersity were evaluated.
  • the number average particle size was 32 nm and MvZMnl.35.
  • the prepared organic pigment particle dispersion (pigment particle concentration: about 0.05 mass%) was used with an ultrafilter to obtain a concentrated pigment liquid (pigment particle concentration: 10 mass%).
  • sodium (Na) The ion concentration was 0.02% by mass.
  • VF35 manufactured by Advantech Toyo Co., Ltd., it was frozen at ⁇ 35 ° C., and then freeze-dried with 6 ⁇ 10 torr for 16 hours to obtain a granular pigment.
  • the pigment composition having the above composition was dispersed with a motor mill M-50 (manufactured by Eiger) at a peripheral speed of 9 m / s using Zircoyu beads having a diameter of 0.65 mm.
  • the pigment composition thus prepared was measured using a nanotrack UPA-EX150 manufactured by Nikkiso Co., Ltd. as a pigment dispersion composition A1, and the particle size and monodispersity were evaluated.
  • a methacrylic acid / benzyl methacrylate copolymer was used to prepare the pigment dispersion composition A1 by using a paste, and a methacrylic acid / benzyl methacrylate / styrene copolymer 15 Pigment dispersion composition as in Pigment dispersion composition A1, except that 8 g (molar ratio 27:60:13, weight average molecular weight: 28,000, 40% 1-methoxy-2-propyl acetate solution) was used.
  • Material B1 was produced.
  • pigment dispersion composition A1 methacrylic acid / benzyl methacrylate copolymer used for preparing the pigment dispersion composition A1 using a paste was added with 15.8 g of polyacrylic acid (mass average molecular weight: 33,3)
  • a pigment dispersion composition C1 was prepared in the same manner as the pigment dispersion composition A1, except that the solution was 1,000, 40% 1-methoxy-2-propyl acetate solution.
  • Pigment dispersion composition B1 was the same as pigment dispersion composition A1 except that when the organic pigment particle dispersion was prepared, a methacrylic acid / benzyl methacrylate copolymer was used. Thus, a pigment dispersion composition Dl was prepared.
  • pigment dispersion composition B1 0.75 g of methacrylic acid / benzyl methacrylate copolymer was used instead of the methacrylic acid / benzyl methacrylate copolymer used in preparing the organic pigment particle dispersion.
  • a pigment dispersion composition E1 was produced in the same manner as the pigment dispersion composition A1, except that it was added during preparation of the product.
  • Table 2 shows the particle size distributions MvZMn of the pigment dispersion compositions A1 to E1.
  • the particle size distribution re-dispersed after ultrafiltration and lyophilization for the purpose of removing salt is organic in the presence of the polymer compound having an acidic group of the present invention.
  • the particles were prepared (pigment dispersion compositions A1 to C1), there was almost no change.
  • pigment dispersion composition D1 When there is no polymer compound having an acidic group when preparing organic particles (pigment dispersion composition D1), or when there is no polymer compound having an acidic group when preparing organic particles, and preparing a pigment dispersion composition
  • a polymer compound having an acidic group corresponding to that amount is sometimes added (pigment dispersion composition E1), the particle size distribution Mv / Mn is slightly changed, but it can be said that there is almost no problem in practical use.
  • Reagent Manufacturer Pigment Red 254 (Ilga Fore Red) Ciba 'Specialty'
  • An organic pigment having a dioxazine structure (C.I. Pigment Violet 23, manufactured by Dainichi Seika Co., Ltd., trade name: NOOLET RE) lg was charged into a sample tube 107 of an apparatus having the configuration shown in FIG.
  • Acetone prepared as solvent 1 to be used as a supercritical fluid was supplied to the sample tube 107 and supplied to the mixer 111 as a pigment-dissolving fluid.
  • water containing 1% by weight of polyvinyl pyrrolidone (trade name: Polybulol pyrrolidone K-30, mass average molecular weight 40, 000, manufactured by Wako Pure Chemical Industries, Ltd.) is prepared as precipitation solvent 2 and supplied to mixer 111. did.
  • the pigment nanoparticle dispersion liquid 115 was prepared and collected by mixing the pigment-dissolving fluid and the precipitation solvent with a mixer.
  • mass ratio of acetone and a precipitation solvent might be set to 1: 1.
  • the temperature of acetone for dissolving pigment (the temperature in sample tube 107) was 245 ° C, and the pressure was 15 MPa.
  • the temperature after mixing with the precipitation solvent was 90 ° C. (outlet temperature of mixer 111).
  • the prepared pigment particle dispersion was evaluated in the same manner as in Example 1. As a result, the pigment particle concentration was about 0.05% by mass.
  • the prepared pigment particles were observed in the same manner as in Example 1. As a result, the number average particle diameter was about 36 nm and Mv / Mn was 1.40.
  • a paste-like concentrated pigment dispersion (pigment particle concentration 33% by mass) was obtained in the same manner as in Example 1.
  • a pigment dispersion composition having the following composition was prepared.
  • the sodium (Na) ion concentration was 0.01 mass% with respect to the pigment.
  • Pigment dispersion from the pigment dispersion composition of the above composition using a motor mill in the same manner as in Example 1.
  • Composition G was made.
  • Example 11 instead of the polymer compound C 1 represented by the general formula (1), methacrylic acid 'benzyl methacrylate copolymer (molar ratio 28Z72, mass average molecular weight 30000, 40% 1-methoxy 2-propyl A pigment dispersion composition H was prepared in the same manner as the pigment dispersion composition G except that the acetate solution was used.
  • An organic pigment particle dispersion was prepared in the same manner as in Example 11.
  • the aqueous dispersion was then agglomerated, washed and filtered in the same manner as in Comparative Example 1 to obtain a desalted and dehydrated paste-like concentrated pigment liquid (pigment particle concentration 31% by mass).
  • the sodium (Na) ion concentration was 0.03 mass 0 / with respect to the pigment. Met.
  • Example 1 Table 3 shows the particle size, the particle size distribution and the number of coarse particles, and the contrast of the pigment dispersion compositions G to I measured in the same manner as in others.
  • the obtained pigment dispersion compositions G to I were each coated on a glass substrate so as to have a thickness of 2 m, thereby preparing samples.
  • a knocklight unit a three-wavelength cold-cathode tube light source (FWL18EX—N manufactured by Toshiba Lighting & Technology Co., Ltd.) with a diffusion plate installed was used, and two polarizing plates (polarizing plate manufactured by Sanritsu Co., Ltd.
  • the pigment dispersion composition of the present invention redispersed in the presence of the compound of the general formula (1) after performing ultrafiltration exhibits a particularly high contrast value, which is a more preferable result.
  • the change in the force at the time of particle formation is large, especially the number of coarse particles is large, and the contrast value is low.
  • thermoplastic resin layer having the following formulation HI On a 75 ⁇ m-thick polyethylene terephthalate film temporary support, using a slit nozzle, a coating solution for a thermoplastic resin layer having the following formulation HI was applied and dried. Next, an intermediate layer coating solution having the following formulation P1 was applied and dried. Furthermore, a light-shielding resin composition K1 having the composition described in Table 4 below was applied and dried, and a thermoplastic resin layer having a dry film thickness of 15 m on the temporary support and a dry film. An intermediate layer with a thickness of 1.6 m and a light-shielding resin layer with a dry film thickness of 2.4 m were provided, and a protective film (polypropylene phenol with a thickness of 12 m) was pressure-bonded.
  • a protective film polypropylene phenol with a thickness of 12 m
  • a photosensitive resin transfer material comprising a temporary support, a thermoplastic resin layer, an intermediate layer (oxygen barrier film), and a light-shielding resin layer was prepared, and the sample name was photosensitive resin.
  • the transfer material was K1.
  • the resin composition Kl having a light-shielding property is obtained by first removing the amount of K pigment dispersion 1 and polypropylene alcohol monomethyl ether acetate in the amounts shown in Table 4 and mixing them at a temperature of 24 ° C ( ⁇ 2 ° C).
  • the surfactant 1 is the same as the surfactant 1 used in the coating solution HI for thermoplastic resin layer.
  • silane coupling liquid N- ⁇ (aminoethyl) y-aminopropyltrimethoxysilane 0.3 mass
  • % Aqueous solution trade name: KBM603, manufactured by Shin-Etsu Chemical Co., Ltd.
  • KBM603 manufactured by Shin-Etsu Chemical Co., Ltd.
  • a rubber roller temperature is applied to the substrate heated at 100 ° C for 2 minutes using a laminator (manufactured by Hitachi Industries, Ltd. (Lamic II type)). Lamination was performed at 130 ° C, linear pressure 100 NZcm, conveyance speed 2. 2 mZ min.
  • a proximity type exposure machine manufactured by Hitachi High-Tech Electronics Engineering Co., Ltd. having an ultra-high pressure mercury lamp with the substrate and mask (quartz exposure mask with image pattern) standing vertically.
  • the distance between the mask surface and the thermoplastic resin layer is set to 20 O / zm, and an exposure energy of lOOmjZcm 2.
  • the mask shape is a lattice shape, and the radius of curvature of the corner that protrudes toward the light-shielding partition wall at the boundary line between the pixel and the light-shielding barrier is 0.6 m.
  • a triethanolamine developer (containing 2.5% triethanolamine, containing a non-ionic surfactant, containing a polypropylene antifoaming agent, trade name: TPD1, Fuji Photo Film) Made by showering at 30 ° C for 50 seconds and a flat nozzle pressure of 0.04 MPa to remove the thermoplastic resin layer and the intermediate layer (oxygen barrier layer).
  • a sodium carbonate developer (0.06 mol Z liters of sodium bicarbonate, sodium carbonate of the same concentration, 1% sodium dibutylnaphthalenesulfonate, ionic surfactant, antifoaming agent, stabilizer, Product name: TCD1, manufactured by Fuji Photo Film Co., Ltd., shower developed at 29 ° C for 30 seconds, cone type nozzle pressure 0.15 MPa, developing a light-shielding resin layer, and patterning separation wall (light-shielding property) Partition wall pattern).
  • plasma water repellency treatment was performed by the following method.
  • Plasma water repellency treatment was performed on the substrate on which the light-shielding partition walls were formed using a force sword coupling parallel plate type plasma processing apparatus under the following conditions.
  • An ink was prepared according to the following formulation with reference to Example 1 of JP-A-2002-201387.
  • composition component content (parts by mass) B ink 1 B ink 2 B ink 3 R ink 1 G ink 1 Pigment dispersion composition G (CIPV 23) 8 Pigment dispersion composition H (CIPV 23) 8 Pigment dispersion composition I (CIPV 23) 8 Pigment dispersion composition J (C. L PR 254) 75 Pigment dispersion composition K (CIPG 36) 75 Pigment dispersion composition (CIPB 15: 6) 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20
  • the pigment and the polymer dispersant were first charged and mixed in a part of the solvent, and the mixture was stirred using a three-roll and bead mill, and then the pigment dispersion liquid was mixed. Got. On the other hand, other compounding ingredients were added to the remainder of the solvent, and dissolved and dispersed by stirring to obtain a binder solution. Then, the pigment dispersion was added little by little to the binder solution and sufficiently stirred with a dissolver to prepare an ink-jet ink for a color filter.
  • Pigment dispersion compositions J, K and L in the same manner as in Example 11 except that Pigment Red 254, Pigment Green 36, or Pigment Blue 15: 6 was used instead of Pigment Violet 23. , Respectively.
  • the R ink 1, G ink 1, and B ink 1 obtained above were first ejected into a recess surrounded by a light-shielding partition as follows using a piezo-type head. And the color filter 1 of this invention was obtained as follows.
  • the head has 2 nozzles with a nozzle density of 25.4 mm and 318 nozzles. Two of these are fixed in the nozzle row direction by shifting the nozzle spacing by 1 Z2 and 25 on the substrate in the nozzle row direction. 300 drops per 4mm.
  • the head and the ink are controlled so that the vicinity of the discharge portion is 50 ° C 0.5 ° C by circulating hot water in the head.
  • the ink ejection of the head force is controlled by a piezo drive signal applied to the head, and it is possible to eject 6 to 42 pl per drop.
  • the glass substrate is conveyed at a position lmm below the head. However, it is ejected from the head.
  • the conveyance speed can be set in the range of 50 to 200 mmZs.
  • the piezo drive frequency can be up to 4.6 KHz, and the droplet ejection volume can be controlled by these settings.
  • the transport speed and drive frequency are controlled so that the amount of pigment applied is 1.1, 1.8, and 0.75gZm 2 for each of R, G, and B.
  • the desired R, G, and B R, G, and B inks were ejected into the recesses corresponding to.
  • UV—LED ultraviolet light emitting diode
  • NCCU033 manufactured by Nichia Corporation was used. This LED outputs ultraviolet light with a wavelength of 365 nm from a single chip.
  • a current of about 500 mA is applied, about lOOmW of light is emitted from the chip.
  • a plurality of these are arranged at intervals of 7 mm, and a power of 0.3 WZcm 2 can be obtained on the surface.
  • the exposure time after droplet ejection and the exposure time can be changed according to the transport speed of the media and the distance between the head and the LED transport direction. After landing, it was dried at 100 degrees for 10 minutes and then exposed.
  • the exposure energy on the media can be adjusted between 0.01 and 15 J Zcm 2 .
  • the exposure energy was adjusted according to the conveyance speed.
  • Spectroradiome A value obtained by integrating the wavelength between 220 nm and 400 nm using URS-40D was used.
  • the glass substrate after droplet ejection was beta-cured in an oven at 230 ° C for 30 minutes, so that both the light-shielding partition and each pixel were completely cured.
  • ITO indium stannate
  • a spacer was formed on the ITO transparent electrode produced in the same manner as the spacer forming method described in [Example 1] of JP-A-2004-240335.
  • a liquid crystal alignment control protrusion was formed on the ITO transparent electrode on which the spacer was formed, using the following positive photosensitive resin layer coating solution.

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  • Spectroscopy & Molecular Physics (AREA)

Abstract

L'invention concerne la production d'une composition contenant des nanoparticules organiques dispersées par un procédé comprenant une étape de mélange d'une solution d'une matière organique dissoute dans un bon solvant avec un solvant médiocre pour la matière organique compatible avec le bon solvant pour générer des nanoparticules organiques à partir de la matière organique, et une étape de concentration de la solution de dispersion obtenue contenant les particules organiques, cette étape de concentration étant réalisée par ultrafiltration de la solution de dispersion.
PCT/JP2006/314700 2005-07-25 2006-07-25 Procédé de production d'une composition contenant des particules organiques dispersées WO2007013475A1 (fr)

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JP2010209161A (ja) * 2009-03-06 2010-09-24 Fujifilm Corp 有機顔料組成物
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JP2011074250A (ja) * 2009-09-30 2011-04-14 Fujifilm Corp 顔料分散物及びそれを用いたインク組成物
JP2015151530A (ja) * 2014-02-19 2015-08-24 富士フイルム株式会社 複合体およびその製造方法、着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置、ならびに、積層体よび積層体
WO2018123103A1 (fr) * 2016-12-28 2018-07-05 Dic株式会社 Composition d'encre, couche de conversion de lumière et filtre de couleur
JPWO2018123103A1 (ja) * 2016-12-28 2018-12-27 Dic株式会社 インク組成物、光変換層及びカラーフィルタ
KR20190098151A (ko) * 2016-12-28 2019-08-21 디아이씨 가부시끼가이샤 잉크 조성물, 광변환층 및 컬러 필터
KR20190098150A (ko) * 2016-12-28 2019-08-21 디아이씨 가부시끼가이샤 분산체 및 그것을 사용한 잉크젯용 잉크 조성물, 광변환층, 및 액정 표시 소자
KR102170059B1 (ko) 2016-12-28 2020-10-27 디아이씨 가부시끼가이샤 잉크 조성물, 광변환층 및 컬러 필터
KR20200122430A (ko) * 2016-12-28 2020-10-27 디아이씨 가부시끼가이샤 잉크 조성물, 광변환층 및 컬러 필터
KR102232006B1 (ko) 2016-12-28 2021-03-25 디아이씨 가부시끼가이샤 분산체 및 그것을 사용한 잉크젯용 잉크 조성물, 광변환층, 및 액정 표시 소자
KR20210034114A (ko) * 2016-12-28 2021-03-29 디아이씨 가부시끼가이샤 분산체 및 그것을 사용한 잉크젯용 잉크 조성물, 광변환층, 및 액정 표시 소자
KR102317627B1 (ko) 2016-12-28 2021-10-26 디아이씨 가부시끼가이샤 잉크 조성물, 광변환층 및 컬러 필터
KR102470362B1 (ko) 2016-12-28 2022-11-25 디아이씨 가부시끼가이샤 분산체 및 그것을 사용한 잉크젯용 잉크 조성물, 광변환층, 및 액정 표시 소자

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