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WO2006051840A1 - Liquide de dispersion de colorant, composition de résine colorée, filtre de couleur et affichage à cristaux liquides - Google Patents

Liquide de dispersion de colorant, composition de résine colorée, filtre de couleur et affichage à cristaux liquides Download PDF

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Publication number
WO2006051840A1
WO2006051840A1 PCT/JP2005/020587 JP2005020587W WO2006051840A1 WO 2006051840 A1 WO2006051840 A1 WO 2006051840A1 JP 2005020587 W JP2005020587 W JP 2005020587W WO 2006051840 A1 WO2006051840 A1 WO 2006051840A1
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Prior art keywords
group
acid
weight
meth
dispersant
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Application number
PCT/JP2005/020587
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English (en)
Japanese (ja)
Inventor
Tatsuhiro Oohata
Toshiya Naruto
Junji Mizukami
Keiko Tanikawa
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Mitsubishi Chemical Corporation
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Priority claimed from JP2005249271A external-priority patent/JP4852935B2/ja
Application filed by Mitsubishi Chemical Corporation filed Critical Mitsubishi Chemical Corporation
Publication of WO2006051840A1 publication Critical patent/WO2006051840A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters

Definitions

  • the present inventors have obtained a stable colorant dispersion with a small amount of dispersant added to the colorant by combining a dispersant having a specific structure.
  • this dispersion has excellent adhesion to the substrate without undissolved matter remaining in the non-image area on the substrate without deteriorating the image forming ability such as curability and high concentration.
  • Color pixels can be formed uniformly, and the tip of the die lip is applied during die coating.
  • the present inventors have found that a colored resin composition in which the generation of dry agglomerates at the ends can be suppressed can be achieved.
  • the present invention comprises a plurality of related inventions, and the gist of each invention is as follows.
  • the color material dispersion of the present invention comprises a color material, a dispersant, and a solvent as essential components, and if necessary, may contain other additives other than the above components.
  • each component will be described.
  • ⁇ represents a divalent linking group, in particular, the number of carbons such as ethylene and propylene.
  • the amine value of the graft copolymer of the present invention is usually 5 to: 100 mgKH / g, preferably 10 to 70 mgKH / g, more preferably 15 to 40 mgKH / g or less. is there. If the amine value is too low, the dispersion stability may decrease and the viscosity may become unstable. Conversely, if the amine value is too high, the residue may increase or the electrical characteristics after the liquid crystal panel is formed may deteriorate.
  • the acrylic block copolymer of component (a) the A block having a quaternary ammonium base and / or amino group in the side chain, the B block having a quaternary ammonium base and / or amino group, Preferred are A-B block copolymers and / or B-A-B block copolymers.
  • the A block constituting the block copolymer of the acrylic block copolymer has a quaternary ammonium base and / or an amino group.
  • the quaternary ammonium base is preferably —N + RRR ⁇ ⁇ — (where R 1, R 2 and R are
  • Y— represents an anion. It has a quaternary ammonium base represented by This quaternary ammonium base may be directly bonded to the main chain, but may be bonded to the main chain via a divalent linking group.
  • Examples of the cyclic structure include a 5- to 7-membered nitrogen-containing heterocyclic monocycle or a condensed ring obtained by condensing two of these.
  • the nitrogen-containing heterocycle is more preferably a saturated ring that is preferably non-aromatic. Specific examples include the following.
  • These cyclic structures may further have a substituent.
  • R in N + RRR may be more preferably la 2a 3a la 3a
  • R ld , R 2d , and R 3d each independently represent a hydrogen atom or an optionally substituted cyclic or chain hydrocarbon group.
  • R ld Two or more of R 2d and R 3d may be bonded to each other to form a cyclic structure
  • R 4d represents a hydrogen atom or a methyl group
  • X represents a divalent linking group
  • Y— represents an anion.
  • examples of the divalent linking group X include, for example, an alkylene group having 1 to 10 carbon atoms, an arylene group, one CONH—R 5d —, one COO R 6d — (provided that R 5d and R 6d are a direct bond, an alkylene group having 1 to 10 carbon atoms, or an ether group having 1 to 10 carbon atoms (one R 7d _ 0 _R 8d —: R 7d and R 8d are each independently Represents an alkylene group), and the like.
  • COO—R M — is preferable.
  • Examples of Y- for anions include Cl-, Br-, ⁇ , CIO-, BF-, CH COO-, and PF-.
  • the amino group is preferably —NR le R 2e (where R le and R 2e are each independently a cyclic or chain-like alkyl group which may have a substituent, or a substituent. It represents a good aryl group or an aralkyl group which may have a substituent, and more preferably an amino group represented by the following formula.
  • R le and R 2e the above R le and R 2e synonymous, R 3e represents an alkylene group, R 4e represents a hydrogen atom or a methyl group having at least one carbon atom.
  • R le and R 2e are preferably methyl groups, R is preferably a methylene group, and ethylene groups are preferred.
  • R 4e is preferably a hydrogen atom. Examples of such a compound include a substituent represented by the following formula.
  • the partial structure containing the specific quaternary ammonium base and / or amino group as described above may be contained in two or more kinds in one A block.
  • two or more kinds of quaternary ammonium base and / or amino group-containing partial structure may be contained in the A block in any form of random copolymerization or block copolymerization.
  • Examples of the partial structure that may be contained in the partial structural force S, A block that does not contain the quaternary ammonium base and / or amino group include (meth) acrylic acid ester monomers described below. Examples include a partial structure derived from the origin.
  • Powerful quaternary ammonium base and / or a partial structure containing no amino group in the A block is preferably 0 to 50% by weight, more preferably 0 to 20% by weight. Most preferably, the ammonium base and / or amino group-free partial structure is not included in the A block.
  • R 9d represents a hydrogen atom or a methyl group.
  • R 1W has a cyclic or chain alkyl group which may have a substituent, or a substituent. Represents an aryl group that may be substituted, or an aralkyl group that may have a substituent.
  • the acrylic dispersant used in the present invention comprises such an A block and a B block.
  • Such a block copolymer is prepared, for example, by the living polymerization method shown below.
  • the polymerization active species is a radical, and is represented by the following scheme, for example.
  • the amount of the class ammonium base is preferably 0.1 to:! Ommol, outside this range, it may not be possible to combine good heat resistance and dispersibility.
  • R la and IT each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
  • R z R db and R 4b represent a hydrogen atom, a hydroxyl group, a halogen atom, an amino group, or an organic group
  • L 1 and L 2 represent a divalent linking group
  • Two or more of L 2 and L 3 may be bonded to each other to form a ring.
  • Ethylene such as acrylonitrile or substituted ethylene compounds; And the like.
  • methyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, and styrene are preferable in terms of good transparency and resistance to heat resistance.
  • these other copolymerizable monomers may be used alone or in combination of two or more.
  • ethylene glycol monoalkyl ether acetates such as ethyl acetate, isopropyl acetate, cellosolve acetate, butylacetate sorb acetate
  • diethylene glycol monoalkyl ethers such as diethylene glycol monomethyl ether acetate, carbitol acetate and butinorecarbitol acetate.
  • Acetates propylene glycol monoalkyl ether acetates;
  • 1, 4_dioxane ethers such as tetrahydrofuran; Acetone, methyl ethyl ketone, ketones such as cyclohexanone, hydrocarbons such as benzene, toluene, xylene, octane, decane; petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, solvent naphtha; methyl lactate , Lactate esters such as ethyl lactate and butyl lactate;
  • Examples thereof include dimethylformamide and N_methylpyrrolidone.
  • These solvents may be used alone or in combination of two or more.
  • the amount of these solvents to be used is 30 to 1000 parts by weight, preferably 50 to 800 parts by weight, with respect to 100 parts by weight of the resulting copolymer. If the amount of solvent used is outside this range, it will be difficult to control the molecular weight of the copolymer.
  • tetrahydrophthalic anhydride and / or succinic anhydride are preferable.
  • the component (Z) one type may be used alone, or two or more types may be used in combination. By adding such components, the binder resin used in the present invention can be made alkali-soluble.
  • glycidinole (meth) acrylate or polymerizable unsaturated group is added to a part of the generated carboxyl group.
  • Such binder resin may be used alone or in combination of two or more. Also good.
  • Such a binder resin particularly in combination with a urethane-based dispersant or an acrylic-based dispersant described later, has excellent adhesion to the substrate without leaving undissolved matter on the non-image area on the substrate.
  • the effect that a color pixel of density can be formed is preferable.
  • Such a binder resin is usually contained in the range of 0.1 to 80% by weight, preferably 1 to 60% by weight in the total solid content of the colored resin composition of the present invention.
  • the content of the binder resin is less than this range, the film becomes brittle and the adhesion to the substrate may be lowered.
  • the amount is larger than this range, the permeability of the developer into the exposed portion increases, and the surface smoothness and sensitivity of the pixel may deteriorate.
  • the photopolymerization initiator is usually used as a mixture (photopolymerization initiator system) with an accelerator and an additive such as a sensitizing dye added as necessary.
  • the photopolymerization initiator system is a component having a function of directly absorbing light or being photosensitized to cause a decomposition reaction or a hydrogen abstraction reaction to generate a polymerization active radical.
  • Examples of the accelerator constituting the photopolymerization initiator component include ⁇ , ⁇ -dimethylaminobenzoic acid ethyl ester, ⁇ , ⁇ -dialkylaminobenzoic acid alkyl ester, 2-mercaptobenzothiothiol, 2_ Mercaptobenzo compounds having a heterocyclic ring such as mercaptobenzoxazole and 2-mercaptobenzoimidazole, or aliphatic polyfunctional mercapto compounds can be used.
  • photopolymerization initiators and accelerators may be used alone or in combination of two or more. May be used in combination.
  • Specific photopolymerization initiator components include, for example, dialkylacetosulfites described on pages 16 to 26 of “Fine Chemical” (1991, March 1 issue, vol. 20, 4 ⁇ ⁇ 4). Hexalylbiimidazole, S-trihalomethyltriazine described in JP-A-58-403023, JP-B-45-37377, etc., such as enones, benzoin and thixanthone derivatives Containing an ethylenic saturated double bond capable of addition polymerization having a titanocene and a xanthene dye, an amino group or a urethane group, as described in JP-A-4-221958, JP-A-4-219756, etc. Examples include systems that combine compounds.
  • the blending ratio of the photopolymerization initiator component is usually from 0.:! To 40% by weight, and preferably from 0.5 to 30% by weight, based on the total solid content of the colored resin composition of the present invention. If the blending ratio is extremely low, the sensitivity to exposure light may be reduced. On the other hand, if it is extremely high, the solubility of the unexposed part in the developer may be lowered, leading to poor development. If necessary, a sensitizing dye corresponding to the wavelength of the image exposure light source can be added to the photopolymerization initiator system component for the purpose of increasing the sensitivity.
  • amino group-containing sensitizing dyes preferred are amino group-containing sensitizing dyes, and more preferred are compounds having an amino group and a phenyl group in the same molecule. Particularly preferred are, for example, 4, 4'-dimethylaminobenzophenone, 4,4'-jetylaminoben zofenone, 2-aminobenzofenone, 4-aminominobenzofoenone, 4,4'-diaminovene.
  • Benzophenes such as zofenone, 3, 3'-daminobenzophenone, 3,4-diaminobenzophenone Enone compounds; 2 — (p-dimethylaminophenyl) benzoxazole, 2— ( ⁇ -dimethylaminophenyl) benzoxazole, 2 -— (p-dimethylaminophenyl) benzo [4, 5 ] Benzoxazole, 2- (p-dimethylaminophenyl) benzo [6,7] benzoxazole, 2,5_bis (p-jetylaminophenyl) 1,3,4-oxazole, 2_ (p_ Dimethylaminophenyl) benzothiazole, 2_ (p-Jetylaminophenenole) benzothiazole, 2- (p-Dimethylaminophenol) benzimidazole, 2_ (p-Jetylaminophenyl) benzimidazole, 2,5_bis
  • the blending ratio of the sensitizing dye in the colored composition for a color filter of the present invention is usually 0 to 20% by weight, preferably 0.:! To 15% by weight, based on the total solid content of the colored resin composition. More preferably, 0.2 to 10% by weight.
  • ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid examples include hydrated quinone diatalylate, hydrated quinone dimetatalylate, resorcin diatalate, resorcin dimetatalylate, pyrogallol tritalylate, and the like. It is done.
  • the ester obtained by the esterification reaction of an unsaturated carboxylic acid with a polyvalent carboxylic acid and a polyvalent hydroxy compound may not necessarily be a single substance but a mixture.
  • Typical examples include condensates of acrylic acid, phthalic acid and ethylene glycol, condensates of acrylic acid, maleic acid and diethylene glycol, condensates of methacrylic acid, terephthalic acid and pentaerythritol, acrylic acid, adipic acid, butanediol and Examples thereof include glycerin condensates.
  • Hexamethylene diisocyanate is an ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a hydroxy compound containing a (meth) atallyloyl group.
  • ethylenic compound used in the present invention include acrylamides such as ethylene bisacrylamide; allylic esters such as diaryl phthalate; vinyl group-containing compounds such as dibule phthalate.
  • One of these monomers may be used alone. However, since it is difficult to use a single compound in production, two or more of these monomers may be used in combination. If necessary, a polyfunctional monomer having no acid group and a polyfunctional monomer having an acid group may be used in combination.
  • the acid value of the polyfunctional monomer having an acid group 0.:! To 40 mg_KOHZg And particularly preferably 5 to 30 mg-KH / g. If the acid value of the polyfunctional monomer is too low, the developing dissolution properties will be lowered, and if it is too high, the production and handling will be difficult, the photopolymerization performance will be lowered, and the curability such as the surface smoothness of the pixels will be inferior. Therefore, when two or more polyfunctional monomers having different acid groups are used in combination, or when a polyfunctional monomer having no acid group is used in combination, the acid groups as the entire polyfunctional monomer are adjusted so as to fall within the above range. It is essential.
  • more preferred polyfunctional monomers having an acid group are dipentaerythritol hexaatalylate, dipentaerythritolorepentatalylate, dipentaerythris commercially available as T 01382 manufactured by Toagosei Co., Ltd. It is a mixture of lithonorepentatalylate containing succinate ester as the main component. A combination of other polyfunctional monomers with this polyfunctional monomer can also be used.
  • the blending ratio of these polyfunctional monomers is usually 5 to 80% by weight, preferably 10 to 70% by weight, based on the total solid content of the colored resin composition of the present invention. %, Preferably 10 to 100 weight. / 0 , more preferably 20 to 80% by weight.
  • the blending ratio of the multifunctional monomer is appropriately adjusted according to the type of the coloring material of the coloring composition and the acid value of the multifunctional monomer used.
  • aromatic carboxylic acids include benzoic acid, toluic acid, cumic acid, hemelic acid, mesitylene acid, phthalic acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, and melophane. Acid, pyromellitic acid, phenylacetic acid, hydroatropic acid, hydrocacinic acid, mandelic acid, phenylsuccinic acid, atropaic acid, kaynic acid, methyl kainate, benzyl kainate, cinnamylidene acetic acid, tamalic acid, umberlic acid, etc. And a carboxylic acid in which a carboxyl group is directly bonded to the phenyl group, a carboxylic acid in which a carboxyl group is bonded to the phenyl group via a carbon bond, and the like.
  • the molecular weight of the organic carboxylic acid is 1000 or less, and usually 50 or more. If the molecular weight of the organic carboxylic acid is too large, the effect of improving soil contamination is insufficient. If the molecular weight is too small, the amount added may be reduced or process contamination may occur due to sublimation or volatilization.
  • a storage stabilizer a surface protective agent, an adhesion improver, a development improver and the like can be added as necessary.
  • the amount of these components added is preferably 20% by weight or less based on the total solid content of the colored composition of the present invention.
  • the colorant dispersion obtained by the dispersion treatment or the like described in [11-5] is blended with a solvent, a binder resin, a polyfunctional monomer, a photopolymerization initiator system component, and, if necessary. Mix other ingredients to make a uniform dispersion.
  • fine dust may be mixed, and thus the obtained colored resin composition is preferably filtered with a filter or the like.
  • the coloring composition for a color filter of the present invention is used as a coating solution for forming a pixel image at least one of black, red, green, and blue.
  • the black resist is formed on the transparent substrate, and the red, green, and blue color resists are formed on the resin black matrix forming surface formed on the transparent substrate, or using a chromium compound or other light shielding metal material.
  • a pixel image of each color is formed on the metal black matrix forming surface by performing coating, heat drying, image exposure, development, and thermosetting.
  • the transparent substrate of the color filter is not particularly limited as long as it is transparent and has adequate strength.
  • the material include polyethylene terephthalate.
  • Polyester resins such as polyester resins, polypropylene resins such as polypropylene and polyethylene, sheets of thermoplastic resins such as polycarbonate, polymethyl methacrylate, and polysulfone, epoxy resins, unsaturated polyester resins, poly (meth) acrylic resins, etc.
  • the transparent substrate and the black matrix forming substrate described later have corona discharge treatment, ozone treatment, silane coupling agent, urethane resin, etc. as necessary.
  • a thin film forming process of various resins may be performed.
  • the black matrix is formed on a transparent substrate using a light-shielding metal thin film or a photosensitive black composition for black matrix.
  • a light-shielding metal thin film or a photosensitive black composition for black matrix As the light-shielding metal material, chromium compounds such as metal chromium, chromium oxide and chromium nitride, nickel and tungsten alloy, etc. are used, and these may be laminated in a plurality of layers.
  • These metal light-shielding films are generally formed by a sputtering method, and after forming a desired pattern in a film shape by a positive type photoresist, cerium nitrate, perchloric acid and / or Alternatively, an etchant mixed with nitric acid is used, and other materials are etched using an etchant suitable for the material. Finally, the positive photoresist is stripped with a special stripper to remove the black matrix. Can be formed.
  • the black composition for black matrix when used, it contains a black color material.
  • the coloring composition is used to form a black matrix.
  • black color materials such as carbon black, black lead, iron black, aniline black, cyanine black, titanium black, etc., or red or green appropriately selected from inorganic or organic pigments and dyes
  • a black matrix can be formed in the same manner as described below for forming a red, green, and blue pixel image using a coloring composition containing a black color material mixed with blue or the like.
  • the coloring composition for the color filter can be applied by a spinner method, a wire bar method, a flow coating method, a die coating method, a roll coating method, a spray coating method, an ink jet method, or the like.
  • the die coating method significantly reduces the amount of coating solution used and suppresses the generation of foreign substances that are completely free from the effects of mist adhering to the spin coating method. To preferred.
  • the thickness of the coating film is usually preferably in the range of 0.2 to 20 xm, more preferably in the range of 0.5 to 10 xm, and still more preferably in the range of 0.2 to 20 xm. It is in the range of 8-5 xm.
  • the drying time is usually selected in the range of 40 to 80 ° C and 15 seconds to 5 minutes, preferably 50 to 70 ° C, depending on the type of solvent component and the performance of the dryer used. Is selected in the range of 30 seconds to 3 minutes.
  • Image exposure is carried out by applying a negative matrix pattern on the dried coating film of the colored composition, and irradiating a UV or visible light source through this mask pattern. At this time, if necessary, exposure may be performed after forming an oxygen blocking layer such as a polyvinyl alcohol layer on the colored composition film in order to prevent a decrease in sensitivity of the colored composition film due to oxygen.
  • an oxygen blocking layer such as a polyvinyl alcohol layer
  • the light source used for image exposure is not particularly limited.
  • Lamp light sources such as fluorescent lamps, and laser light sources such as argon ion lasers, YAG lasers, excimer lasers, nitrogen lasers, helium cadmium lasers, and semiconductor lasers.
  • An optical filter can also be used when irradiating light of a specific wavelength.
  • Development can be performed after the image exposure using an organic solvent or an aqueous solution containing a surfactant and an alkaline compound.
  • This aqueous solution may further contain an organic solvent, a buffering agent, a complexing agent, a dye or a pigment.
  • alkaline compounds include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium silicate, Inorganic alkaline compounds such as potassium silicate, sodium metasilicate, sodium phosphate, potassium phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium hydroxide, Mono-di- or triethanolamine, mono-di- or tri-methylamine, mono-one di- or triethylamine, mono- or diisopropylamine, n-butylamine, mono-di- or triisopropanolamine, Examples include organic alkaline compounds such as ethyleneimine, ethylenedimine, tetramethylammonium hydroxide (TMAH), and choline. These alkaline compounds may be used singly or in combination of two or more.
  • TMAH tetramethylammonium hydroxide
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, and monoglyceride alkyl esters.
  • Anionic surfactants such as alkylbenzene sulfonates, alkylnaphthalene sulfonates, alkyl sulfates, alkyl sulfonates, and sulfosuccinate esters, and amphoteric surfactants such as alkyl betaines and amino acids. These may be used alone or in combination of two or more.
  • the development processing conditions are not particularly limited. Usually, the development temperature is in the range of 10 to 50 ° C, particularly 15 to 45 ° C, particularly preferably 20 to 40 ° C.
  • the development method is immersion development or spray development. , Brush developing method, ultrasonic developing method and the like.
  • the color filter substrate after development is usually subjected to heat curing treatment or light curing treatment, preferably heat curing treatment.
  • the color filter according to the present invention forms a transparent electrode such as ITO on the image as it is and is used as a part of a component such as a color display or a liquid crystal display device. If necessary, a top coat layer such as polyamide or polyimide can be provided on the image.
  • the transparent electrode may not be formed.
  • the liquid crystal display device of the present invention usually forms an alignment film on the color filter of the present invention, spreads a spacer on the alignment film, and then adheres it to a counter substrate to form a liquid crystal cell. It is manufactured by injecting liquid crystal into the formed liquid crystal cell and connecting it to the counter electrode.
  • the bonding gap with the counter substrate varies depending on the application of the liquid crystal display device, but is usually selected in the range of 2 to 8 zm.
  • the portion is sealed with a sealing material such as an epoxy resin.
  • the sealing material is cured by irradiation with ultraviolet rays (UV) and / or heating, and the periphery of the liquid crystal cell is sealed.
  • thermo-pick pick liquid crystals There are no particular restrictions on the type of liquid crystal, and conventionally known liquid crystals such as aromatic, aliphatic, and polycyclic compounds are used, and any of lyotropic liquid crystals, thermotropic liquid crystals, and the like may be used. Nematic liquid crystal, smectic liquid crystal, and cholesteric liquid crystal are known as thermo-pick pick liquid crystals.
  • a degassed solution of 200 mg of this oligomer and 10 ml of dimethylaminoethyl methacrylate was heated at 120 ° C. for 1 hour.
  • dimethyl-1,2,1, [oxybis (methylene)] bis_2_propenoate 40 parts by weight, methacrylic acid 32 parts by weight, methyl methacrylate 66 parts by weight, methacrylic acid in the monomer tank 62 parts by weight of benzyl, 2.6 parts by weight of t-butylperoxy-2-ethylhexanoate, 40 parts by weight of propylene glycol monomethyl ether acetate, 5.2 parts by weight of n-dodecyl mercaptan in the chain transfer agent tank, 27 parts by weight of propylene glycol monomethyl ether acetate After the temperature of the reaction vessel was stabilized at 90 ° C, dropping was started from the monomer tank and the chain transfer agent tank to initiate polymerization.
  • a separable flask equipped with a cooling tube was prepared as a reaction tank, while 60 parts of dimethylolene 2,2 '-[oxybis (methylene)] bis-2-propenoate and methacrylate were added as a monomer dropping tank. 60 parts, 80 parts of benzyl methacrylate, t-butyl peroxy -2-ethyl hexanoate (“Perbutyl 0” manufactured by NOF Corporation) and 60 parts of diethylene glycol dimethyl ether are mixed and prepared. As a chain transfer agent dropping tank, 8 parts of n-dodecanethiol and 32 parts of diethylene glycol dimethyl ether were prepared with sufficient stirring and mixing.
  • the mixture was stirred while purging 145 parts by weight of propylene glycol monomethyl ether acetate with nitrogen, and the temperature was raised to 80 ° C. Thereto were added dropwise 20 parts by weight of a polymethyl methacrylate macromonomer, 15 parts of 2-hydroxyethyl methacrylate, 10 parts of benzyl methacrylate and 35 parts of methacrylic acid, and the mixture was further stirred for 2 hours.
  • Propylene glycol monomethyl ether acetate 35 parts, 1-methoxy_2_propanol 8.8 parts, V-59 (Wako Pure Chemical Industries, Ltd. azo polymerization initiator) 1. Charge 5 parts into a reaction vessel and add nitrogen. In an atmosphere, the temperature was raised to 80 ° C., 9.5 parts of benzyl methacrylate and 6.5 parts of methinoremethalelate 6.5- ⁇ -hydroxyethinoremethacrylateate 3.5 ⁇ ⁇ methacryloleic acid 10.7 ⁇ for 2 hours The mixture was added dropwise and further stirred for 4 hours to obtain a polymerization reaction solution.
  • CI pigment green 36 as a coloring material 7.20 parts by weight, CI pigment yellow 150 3.09 parts by weight, propylene glycol monomethyl ether acetate as a solvent 60.00 parts by weight, as a dispersant described in Table 1 Dispersant (a) or Dispersant E in total in terms of solid content 1.29 parts by weight, Dispersant (b) or Dispersant L, M listed in Table 1-1, 3.43 parts by weight, diameter 0.5 mm
  • a stainless steel container was filled with 225 parts by weight of Zirco Your beads and dispersed in a paint shaker for 6 hours to prepare a green pigment dispersion.
  • the viscosity (20 rpm) immediately after production of the pigment dispersion and after standing in a thermostat at 23 ° C. for 7 days was measured using an E-type viscometer “RE-80L” manufactured by Toki Sangyo Co., Ltd.
  • the viscosity of the pigment dispersions in each of the examples and comparative examples was compared with the rate of change in viscosity over 7 days. 1. Those that were 7% or more were ⁇ , 1 ⁇ 7% or more and less than 5% ⁇ , X from 5% to less than 10%, and XX from 10% or more. The results are shown in Table 1.
  • Dispersant E represents a Kusumoto Chemicals, Ltd. polyether amine phosphate salt" DA3 7 5 J. 2) Preparation of Dispersant F denotes the one company made rDi spe rbyW61J Bikkukemi. [7] colored resin composition
  • Example 18 was carried out in the same manner as Example 15 except that Dispersant I was used as the binder resin instead of the binder X of Example 15.
  • Table 2 Table _2 (Examples 1 to 4, 1 3 to 1 7, 1 9, Comparative Examples 1, 3, 4)
  • Binder resin Y The resin of Synthesis Example 6 (dispersant H) was used as the binder resin.
  • the colored resin compositions of Examples and Comparative Examples were each applied to a 50 mm square glass substrate by a spin coating method with a dry film thickness of 2.5 zm and air-dried for 60 minutes. Thereafter, it is immersed in 6.25 g of the solvent that forms the colored composition for 3 minutes, redispersed, and after 10 minutes, The particle size distribution was measured with an instrumental Microtrac UPA, and the volume average particle size mv was calculated. A sample having a volume average particle diameter mv of less than 200 nm was designated as ⁇ , and a particle having a volume average particle size of 200 nm or more was designated as X. The results are shown in Table 1.
  • the occurrence rate of foreign matter defects by the die coating method was 0%, which corresponds to the volume average particle diameter mv in re-dissolvability being 200 nm or less.
  • the sample was exposed at 60 mj / cm 2 through a mask pattern using a high-pressure mercury lamp, and then developed using a 0.04 wt% aqueous potassium hydroxide solution at a developer temperature of 23 ° C. After the image formation, it was rinsed with sufficient water and then dried with clean air. After that, post-beta was performed in an oven at 230 ° C for 30 minutes. The film thickness after drying was about 1.8 / m.
  • the non-image area (on the color filter) of Sampu Nore obtained in [9] was wiped 10 times with a dust-free cloth soaked with 100% ethanol (Toraysee MK Clean Cloth). .
  • the dust-free cloth was fixed to the tip of a lcm x lcm resin square and impregnated with 0. Ice ethanol using a dropper.
  • the pigment adhesion to the dust-free cloth was visually observed, and the presence or absence of the coloring composition in the non-image area after development was evaluated according to the following criteria. as a result Are shown in Table 1.
  • Table 1 shows that the color filter using the colored resin composition of the example showed no or very little residue by visual observation, whereas Comparative Examples 1 and 2 had poor dispersibility and could not be evaluated. In the color filters using the colored resin compositions of Comparative Examples 5 and 6, visual residue was clearly observed.
  • the colorant dispersion of the present invention has good dispersion stability (no change in viscosity), and the colored resin composition of the present invention has a foreign matter defect suppressing effect, curability, antifouling effect, and It was confirmed that the anti-shrinking effect was also excellent.
  • the present invention has very high industrial applicability in the fields of colorant dispersions, photosensitive coloring compositions, color filters, and liquid crystal display devices for the following reasons (1) to (4). .
  • a colored resin composition is formed on the non-image area on the substrate when applied on the substrate. It is possible to produce a color filter having a high concentration and a low film thickness that does not deteriorate the image forming ability such as curability, and has excellent adhesion to the substrate with little undissolved material remaining.
  • the undissolved colored resin composition when coated on a substrate, is less likely to remain in the non-image area on the substrate. It is possible to produce a color filter with a high density and a low film thickness without reducing the image forming ability, etc., and when applying by die coating, dry aggregation at the tip of the die lip is suppressed, and a color filter is produced with a high yield.
  • the photosensitive coloring composition to be obtained can be provided.
  • the non-pixel portion on the substrate has no undissolved photosensitive coloring composition or foreign matter resulting from dry aggregation at the time of die coating application, and has a high concentration and a low film thickness. High quality color filters can be provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)

Abstract

L’invention concerne un liquide de dispersion de colorant permettant de réduire la quantité de composition colorée photosensible non dissoute restant dans les portions hors image sur un substrat, lorsque l’on applique ledit liquide sur le substrat. Le liquide de dispersion de colorant présente une excellente adhérence au substrat et ne compromet pas les propriétés de formation d’image comme l’aptitude à la cuisson, de sorte qu’il permet de produire un filtre de couleur de forte concentration et de faible épaisseur de film. De plus, comme on supprime le séchage et l’engorgement au niveau du bord de lèvre de la filière pendant l’application de ce liquide de dispersion de colorant par enduction à filière, ce liquide de dispersion de colorant permet d’obtenir un filtre de couleur avec un rendement élevé. L’invention divulgue spécifiquement un liquide de dispersion de colorant contenant un colorant (A), un agent dispersant (B) et un solvant (C) qui est caractérisé en ce que l’agent dispersant (B) contient au moins un copolymère greffé (a) contenant un atome d’azote et un polymère (b) que l’on obtient en polymérisant un composant monomère contenant essentiellement un composé spécifique.
PCT/JP2005/020587 2004-11-11 2005-11-10 Liquide de dispersion de colorant, composition de résine colorée, filtre de couleur et affichage à cristaux liquides WO2006051840A1 (fr)

Applications Claiming Priority (4)

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JP2004-327629 2004-11-11
JP2004327629 2004-11-11
JP2005-249271 2005-08-30
JP2005249271A JP4852935B2 (ja) 2005-08-30 2005-08-30 色材分散液、着色樹脂組成物、カラーフィルタ、及び液晶表示装置

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008179750A (ja) * 2006-12-27 2008-08-07 Kao Corp 非水系顔料分散組成物
JP2009084450A (ja) * 2007-09-28 2009-04-23 Fujifilm Corp 顔料分散組成物、光硬化性組成物、カラーフィルタ、液晶表示素子および固体撮像素子
CN112011193A (zh) * 2019-05-29 2020-12-01 阪田油墨股份有限公司 彩色滤光片用颜料分散组合物及彩色滤光片用颜料分散抗蚀剂组合物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08109347A (ja) * 1994-10-07 1996-04-30 Mitsubishi Rayon Co Ltd 調色用ベースレジン
JPH09503243A (ja) * 1993-09-30 1997-03-31 エル．ヴェ．エム．アッシュ． ルシェルシェ 固体粒子用の湿潤および／または分散剤としてのアクリル系ブロック共重合体、並びに生成する分散物の利用法
JPH09176511A (ja) * 1995-12-21 1997-07-08 Nippon Steel Chem Co Ltd 顔料分散体組成物およびカラーレジストインキ
JP2002523580A (ja) * 1998-09-02 2002-07-30 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー アクリル主鎖、ポリエステル側鎖、環状イミド基および第四級アンモニウム基を有する高分子顔料分散剤
JP2002212447A (ja) * 2001-01-11 2002-07-31 Hitachi Maxell Ltd 分散液組成物及びこれを用いたインクジェットプリンタ用インク

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09503243A (ja) * 1993-09-30 1997-03-31 エル．ヴェ．エム．アッシュ． ルシェルシェ 固体粒子用の湿潤および／または分散剤としてのアクリル系ブロック共重合体、並びに生成する分散物の利用法
JPH08109347A (ja) * 1994-10-07 1996-04-30 Mitsubishi Rayon Co Ltd 調色用ベースレジン
JPH09176511A (ja) * 1995-12-21 1997-07-08 Nippon Steel Chem Co Ltd 顔料分散体組成物およびカラーレジストインキ
JP2002523580A (ja) * 1998-09-02 2002-07-30 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー アクリル主鎖、ポリエステル側鎖、環状イミド基および第四級アンモニウム基を有する高分子顔料分散剤
JP2002212447A (ja) * 2001-01-11 2002-07-31 Hitachi Maxell Ltd 分散液組成物及びこれを用いたインクジェットプリンタ用インク

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008179750A (ja) * 2006-12-27 2008-08-07 Kao Corp 非水系顔料分散組成物
JP2009084450A (ja) * 2007-09-28 2009-04-23 Fujifilm Corp 顔料分散組成物、光硬化性組成物、カラーフィルタ、液晶表示素子および固体撮像素子
CN112011193A (zh) * 2019-05-29 2020-12-01 阪田油墨股份有限公司 彩色滤光片用颜料分散组合物及彩色滤光片用颜料分散抗蚀剂组合物
CN112011193B (zh) * 2019-05-29 2024-01-05 阪田油墨股份有限公司 彩色滤光片用颜料分散组合物及彩色滤光片用颜料分散抗蚀剂组合物

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