WO2013080964A1 - Composition colorée pour filtre coloré, et filtre coloré - Google Patents

Composition colorée pour filtre coloré, et filtre coloré Download PDF

Info

Publication number
WO2013080964A1
WO2013080964A1 PCT/JP2012/080601 JP2012080601W WO2013080964A1 WO 2013080964 A1 WO2013080964 A1 WO 2013080964A1 JP 2012080601 W JP2012080601 W JP 2012080601W WO 2013080964 A1 WO2013080964 A1 WO 2013080964A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
resin
color filter
parts
meth
Prior art date
Application number
PCT/JP2012/080601
Other languages
English (en)
Japanese (ja)
Inventor
深雪 田中
三上　譲司
鈴木　雄太
奈津子 小久保
章乃 宮川
由昌 宮沢
Original Assignee
東洋インキＳｃホールディングス株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2011261667A external-priority patent/JP6205679B2/ja
Application filed by 東洋インキＳｃホールディングス株式会社 filed Critical 東洋インキＳｃホールディングス株式会社
Priority to CN201280059244.6A priority Critical patent/CN103959109B/zh
Priority to KR1020147015898A priority patent/KR102004436B1/ko
Publication of WO2013080964A1 publication Critical patent/WO2013080964A1/fr

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a colored composition for a color filter used for manufacturing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter including a filter segment formed using the same. is there.
  • liquid crystal display devices have been evaluated for their space-saving properties, light weight, and power-saving properties due to their thinness, and recently they are rapidly spreading to television applications.
  • it is required to further improve the performance such as brightness and contrast, and further improvement of the transmittance and enhancement of the contrast are desired for the color filter which is a member of the color liquid crystal display device. ing.
  • the color filter As a method for producing the color filter, after forming a pattern with a photoresist, a dyeing method for dyeing the pattern, or by forming a transparent electrode of a predetermined pattern in advance, and using a pigment-containing resin dissolved and dispersed in a solvent by voltage application Electrodeposition method for ionization and pattern formation, printing method such as offset printing using ink containing thermosetting resin or ultraviolet curable resin, pigment dispersion using color resist agent in which colorant such as pigment is dispersed in photoresist material Laws, etc. are known. Recently, the pigment dispersion method has become mainstream. However, in a color filter using a pigment as a colorant, the degree of polarization controlled by the liquid crystal is disturbed due to light scattering by pigment particles. As a result, there is a problem that the luminance and contrast of the color liquid crystal display device are likely to be reduced.
  • a color filter using a salt of an anionic dye and a cationic surfactant as a colorant has been proposed (for example, see Patent Documents 2 and 3).
  • the solubility of an anionic dye in an organic solvent is increased by changing the sodium sulfonate group (—SO 3 Na) of the anionic dye to an organic amine salt.
  • the solubility of the anionic dye in an organic solvent is increased by changing the sodium sulfonate group of the anionic dye to the base salt of the cationic surfactant.
  • sufficient solubility cannot be obtained with respect to the solvent used when producing the color filter.
  • salt forming compounds of anionic dyes those using a cationic resin as a counter have been studied as crystalline aqueous coloring materials (see, for example, Patent Document 4). In color filter applications that require use in a dissolved state, detailed studies have not been made.
  • the object of the present invention is to provide a color filter coloring composition having excellent storage stability, and no foreign matter is generated in the coating film, and has strong adhesiveness with a transparent substrate such as glass, and has excellent heat resistance and resistance.
  • the object is to provide a color filter having high solvent properties and excellent alkali solubility.
  • the present inventors have found that the resin (B) having a cationic group in the side chain, that is, having a cationic group in the side chain, and having a crosslinkable functional group.
  • a coloring composition for a color filter containing a salt-forming compound (D) obtained by reacting an acrylic resin satisfying at least one having a glass transition temperature of 50 ° C. or higher and an anionic dye (C) has been found that it has high storage stability, no foreign matter is generated on the coating film, is excellent in adhesion, and exhibits high heat resistance in a heat resistance test, and the present invention has been made based on this finding.
  • the present invention is a color filter coloring composition
  • a colorant (A) contains a salt-forming compound (D) obtained by reacting a resin (B) having a cationic group in the side chain with an anionic dye (C),
  • the resin (B) having a cationic group in the side chain is an acrylic resin containing a structural unit represented by the following general formula (1), and the acrylic resin has an acrylic resin having a thermally crosslinkable functional group
  • the present invention relates to a coloring composition for a color filter, which is selected from an acrylic resin having a glass transition temperature of 50 ° C. or higher and an acrylic resin having a thermally crosslinkable functional group and a glass transition temperature of 50 ° C. or higher.
  • R 1 represents a hydrogen atom or a substituted or unsubstituted alkyl group.
  • R 2 , R 3 , and R 4 are each independently substituted with a hydrogen atom or an arbitrary substituent.
  • Q represents an alkylene group, an arylene group, —CONH—R 5 —, or —COO—R 5 —
  • R 5 represents an alkylene group
  • Y ⁇ represents Represents an inorganic or organic anion.
  • the thermally crosslinkable functional group is at least one selected from the group consisting of hydroxyl group, carboxyl group, oxetane group, t-butyl group, isocyan
  • the acrylic resin including the structural unit represented by the general formula (1) is a copolymer including a structural unit having a thermally crosslinkable functional group, and the copolymer is the thermal crosslinked
  • the color filter coloring composition according to the invention which contains 10 to 35% by weight of a structural unit having a functional functional group out of a total of 100% by weight.
  • the present invention relates to the coloring composition for a color filter, wherein the thermally crosslinkable functional group contains a hydroxyl group.
  • the present invention relates to the coloring composition for a color filter, wherein the thermally crosslinkable functional group is a hydroxyl group and a carboxyl group.
  • the present invention relates to the color composition for color filters, wherein the acrylic resin containing the structural unit represented by the general formula (1) has an ammonium salt value of 10 to 200 mgKOH / g.
  • the salt-forming compound (D) is a mixture of a resin (B) having a cationic group in the side chain and an anionic dye (C) in an aqueous solution, and having a cationic group in the side chain.
  • the present invention relates to the coloring composition for a color filter, which is a compound prepared by removing a salt composed of a counter anion of a resin (B) and a counter cation of an anionic dye (C).
  • the present invention relates to the coloring composition for a color filter, wherein the main component of the organic solvent is propylene glycol monomethyl ether acetate.
  • the present invention also relates to the color filter coloring composition, wherein the colorant further contains a pigment.
  • the present invention also relates to the color filter coloring composition, further comprising a photopolymerizable monomer and / or a photopolymerization initiator.
  • the present invention also relates to a color filter formed from the coloring composition for a color filter.
  • the resin (B) having a cationic group in the side chain that is, at least one having a cationic group in the side chain and a crosslinkable functional group, or having a glass transition temperature of 50 ° C. or higher.
  • a coloring composition for a color filter containing a salt-forming compound (D) obtained by reacting a filling acrylic resin with an anionic dye (C) it has high storage stability and forms a coating film. There is no generation of foreign matter at the time, and it is possible to obtain a color filter which is excellent in adhesion, exhibits high heat resistance and solvent resistance, and exhibits excellent alkali development.
  • the coloring composition for a color filter of the present invention is obtained by reacting a resin (B) having a cationic group in a side chain with an anionic dye (C) in a colorant carrier containing a binder resin and an organic solvent. It is a coloring composition for color filters containing the obtained salt-forming compound (D). First, the resin (B) having a cationic group in the side chain will be described.
  • the resin (B) having a cationic group in the side chain of the present invention is an acrylic resin containing a structural unit represented by the following general formula (1), an acrylic resin having a thermally crosslinkable functional group, and a glass transition temperature. Is selected from an acrylic resin having a thermal crosslinkable functional group and a glass transition temperature of 50 ° C. or higher.
  • the acrylic resin is preferably an acrylic resin having a thermally crosslinkable functional group and a glass transition temperature of 50 ° C. or higher.
  • the salt-forming compound (D) of the present invention can be obtained when the cationic group represented by the following general formula (1) forms a salt with the anionic group of the anionic dye (C).
  • R 1 represents a hydrogen atom or a substituted or unsubstituted alkyl group.
  • R 2 , R 3 , and R 4 are each independently substituted with a hydrogen atom or an arbitrary substituent. Represents an alkyl group that may be substituted, an alkenyl group that may be substituted with any substituent, or an aryl group that may be substituted with any substituent; 2 of R 2 , R 3 , and R 4 May be bonded to each other to form a ring, Q represents an alkylene group, an arylene group, —CONH—R 5 —, or —COO—R 5 —, R 5 represents an alkylene group, and Y ⁇ represents Represents an inorganic or organic anion.)
  • R 1 represents a hydrogen atom or a substituted or unsubstituted alkyl group.
  • Examples of the alkyl group for R 1 include a methyl group, an ethyl group, a propyl group, an n-butyl group, an i-butyl group, a t-butyl group, an n-hexyl group, and a cyclohexyl group.
  • the alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, and particularly preferably an alkyl group having 1 to 4 carbon atoms.
  • examples of the substituent include a hydroxyl group and an alkoxyl group.
  • R 1 is most preferably a hydrogen atom or a methyl group.
  • R 2 , R 3 , and R 4 are each independently a hydrogen atom, an alkyl group that may be substituted with an arbitrary substituent, or an arbitrary substituent. It may be an alkenyl group or an aryl group optionally substituted by any substituent.
  • a linear alkyl group (methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-octyl, n-decyl, n- Dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, etc.), branched alkyl groups (isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl, 2-ethylhexyl and 1,1, 3,3-tetramethylbutyl and the like), cycloalkyl groups (such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl) and
  • alkenyl groups for R 2 , R 3 and R 4 include linear or branched alkenyl groups (vinyl, allyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1- Methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, etc.), cycloalkenyl groups (2-cyclohexenyl, 3-cyclohexenyl, etc.) Can be mentioned.
  • the alkenyl group is preferably an alkenyl group having 2 to 18 carbon atoms, and more preferably an alkenyl group having 2 to 8 carbon atoms.
  • aryl groups in R 2 , R 3 , and R 4 include monocyclic aryl groups (such as phenyl), condensed polycyclic aryl groups (such as naphthyl, anthracenyl, phenanthrenyl, anthraquinolyl, fluorenyl, and naphthoquinolyl) and aromatic heterocycles Ring hydrocarbon group (thienyl (group derived from thiophene), furyl (group derived from furan), pyranyl (group derived from pyran), pyridyl (group derived from pyridine), 9-oxoxanthenyl (Groups derived from xanthone) and 9-oxothioxanthenyl (groups derived from thioxanthone)).
  • monocyclic aryl groups such as phenyl
  • condensed polycyclic aryl groups such as naphthyl, anthracenyl, phenanthrenyl, anthra
  • the substituent include a halogen atom, a hydroxyl group, an alkoxyl group, an aryloxy group, and an alkenyl group.
  • the substituent is particularly preferably a halogen atom, a hydroxyl group, an alkoxyl group, or a phenyl group.
  • R 2 , R 3 and R 4 are preferably an alkyl group which may be substituted, and more preferably an unsubstituted alkyl group, from the viewpoint of stability.
  • R 2 , R 3 and R 4 may be bonded to each other to form a ring.
  • Q connecting the acrylic moiety and the ammonium base represents an alkylene group, an arylene group, —CONH—R 5 —, or —COO—R 5 —
  • R 5 represents an alkylene group.
  • Q is preferably —CONH—R 5 — or —COO—R 5 —, more preferably —COO—R 5 —, from the viewpoints of polymerizability and availability.
  • R 5 is more preferably a methylene group, an ethylene group, a propylene group, or a butylene group, and particularly preferably an ethylene group.
  • the component Y ⁇ in the general formula (1) constituting the counter anion of the resin may be an inorganic or organic anion.
  • the counter anion known ones can be used without limitation. Specifically, hydroxide ions; halogen ions such as chloride ions, bromide ions, and iodide ions; carboxylate ions such as formate ions and acetate ions; Carbonate ions, bicarbonate ions, nitrate ions, sulfate ions, sulfite ions, chromate ions, dichromate ions, phosphate ions, cyanide ions, permanganate ions, and even hexacyanoferrate (III) ions And complex ions.
  • a halogen ion or a carboxylate ion is preferable, and a halogen ion is most preferable.
  • the counter anion is an organic acid ion such as a carboxylate ion
  • the organic acid ion may be covalently bonded in the resin to form an inner salt.
  • the acrylic resin containing the structural unit represented by the general formula (1) can be obtained by carrying out a copolymerization reaction using an ethylenically unsaturated monomer having an ammonium base as a monomer component.
  • the acrylic resin is synthesized by carrying out a copolymerization reaction using an ethylenically unsaturated monomer having an amino group as a monomer component, and then synthesizing an acrylic resin having an amino group. It can be obtained by reacting with A and carrying out ammonium chloride.
  • ethylenically unsaturated monomer having an ammonium base the ethylenically unsaturated monomer having an amino group
  • an onium chlorinating agent an onium chlorinating agent.
  • acryl, methacryl it may describe as “(meth) acryl”.
  • acryloyl and methacryloyl it may be described as “(meth) acryloyl”.
  • Examples of ethylenically unsaturated monomers having an ammonium base include (meth) acryloyloxyethyltrimethylammonium chloride, (meth) acryloyloxyethyltriethylammonium chloride, (meth) acryloyloxyethyldimethylbenzylammonium chloride, (meth) acryloyl Alkyl (meth) acrylate quaternary ammonium salts such as oxyethylmethylmorpholino ammonium chloride, (meth) acryloylaminopropyltrimethylammonium chloride, (meth) acryloylaminoethyltriethylammonium chloride, (meth) acryloylaminoethyldimethylbenzylammonium chloride Alkyl (meth) acryloylamide quaternary ammonium salts such as dimethyldi Lil ammonium methyl sulfate
  • Examples of ethylenically unsaturated monomers having amino groups include dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dipropylaminoethyl (meth) acrylate, diisopropylaminoethyl (meth) acrylate, dibutylaminoethyl (Meth) acrylate, diisobutylaminoethyl (meth) acrylate, di-t-butylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide, dipropylaminopropyl (meth) acrylamide, diisopropylamino Propyl (meth) acrylamide, dibutylaminopropyl (meth) acrylamide, diisobutylaminopropyl (meth) acrylamide
  • onium chlorinating agents examples include alkyl sulfates such as dimethyl sulfate, diethyl sulfate, or dipropyl sulfate, sulfonate esters such as methyl p-toluenesulfonate, or methyl benzenesulfonate, methyl chloride, ethyl chloride, propyl chloride, or octyl.
  • alkyl chlorides such as chloride, alkyl bromides such as methyl bromide, ethyl bromide, propyl bromide, and octyl chlorobromide, benzyl chloride, and benzyl bromide.
  • the reaction between the ethylenically unsaturated monomer having an amino group and the onium chlorinating agent is usually performed by dropping an equimolar amount or less of the onium chlorinating agent into the amino group-containing ethylenically unsaturated monomer solution. Can be done.
  • the temperature during the ammonium chlorination reaction is about 90 ° C. or less, particularly about 30 ° C. or less when the vinyl monomer is ammonium chlorinated, and the reaction time is about 1 to 4 hours.
  • an alkoxycarbonylalkyl halide can also be used as an onium chloride agent.
  • the alkoxycarbonylalkyl halide is represented by the following general formula (2).
  • Z—R 6 —COOR 7 general formula (2) (In the general formula (2), Z is a halogen such as chlorine or bromine, preferably bromine, and R 6 has 1 to 6 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to carbon atoms.
  • R 7 is a lower alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms.
  • the acrylic resin having a thermally crosslinkable functional group of the present invention forms a crosslink with an acrylic resin having a thermally crosslinkable functional group or a binder resin in a heating step in the production of a color filter. Thereby, a strong film is formed and the color change of the film is prevented. That is, heat resistance can be improved. Moreover, solvent resistance can also be improved.
  • the suitable structure of the thermally crosslinkable functional group is not particularly limited, and examples thereof include a hydroxyl group, a carboxyl group, a carboxylic acid anhydride, a primary or secondary amino group, an imino group, an oxetanyl group, a t-butyl group, Examples thereof include an epoxy group, a mercapto group, an isocyanate group, an allyl group, and a (meth) acryl group.
  • a hydroxyl group, a carboxyl group, an oxetanyl group, a t-butyl group, an isocyanate group, and a (meth) acryl group are preferable.
  • it preferably has a hydroxyl group.
  • One method for introducing a thermally crosslinkable functional group into an acrylic resin is to convert an ethylenically unsaturated monomer having a thermally crosslinkable functional group into an ethylenically unsaturated group corresponding to the cationic group represented by the general formula (1). This is a method of copolymerizing with a saturated monomer.
  • Examples of the ethylenically unsaturated monomer having a hydroxyl group are not particularly limited.
  • 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate examples thereof include glycerol mono (meth) acrylate, 4-hydroxyvinylbenzene, 2-hydroxy-3-phenoxypropyl acrylate, and caprolactone adducts of these monomers (addition mole number is preferably 1 to 5).
  • Examples of the ethylenically unsaturated monomer having a carboxyl group include acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid, etc., and ethylenic having a carboxylic anhydride group.
  • Examples of the unsaturated monomer include maleic anhydride and itaconic anhydride.
  • Examples of the ethylenically unsaturated monomer having an oxetanyl group include 3- (acryloyloxymethyl) 3-methyloxetane, 3- (methacryloyloxymethyl) 3-methyloxetane, 3- (acryloyloxymethyl) 3-ethyloxetane, 3- (methacryloyloxymethyl) 3-ethyloxetane, 3- (acryloyloxymethyl) 3-butyloxetane, 3- (methacryloyloxymethyl) 3-butyloxetane, 3- (acryloyloxymethyl) 3-hexyloxetane and 3- (Methacryloyloxymethyl) 3-hexyloxetane and the like.
  • Examples of the ethylenically unsaturated monomer having a t-butyl group include t-butyl acrylate and t-butyl methacrylate.
  • Examples of the ethylenically unsaturated monomer having an isocyanate group include 2-isocyanate ethyl methacrylate, 2-isocyanate ethyl acrylate, 4-isocyanate butyl methacrylate, 4-isocyanate butyl acrylate, and the like.
  • the isocyanate group in the present invention includes a blocked isocyanate group and can be preferably used. Under normal conditions, the blocked isocyanate group can protect the isocyanate group with other functional groups to suppress the reactivity of the isocyanate group, and can be deprotected by heating to regenerate the active isocyanate group.
  • the isocyanate block body is shown.
  • Examples of commercially available ethylenically unsaturated monomers having such a blocked isocyanate group include 2-[(3,5-dimethylpyrazolyl) carboxyamino] ethyl methacrylate (Karenz MOI-BP, Showa Denko); Examples include 2- (0- [1′methylpropylideneamino] carboxyamino) ethyl methacrylate (Karenz MOI-BM, manufactured by Showa Denko).
  • the ethylenically unsaturated monomer having a blocked isocyanate group a commercially available product can be used, and it can also be prepared and used by a known method.
  • an isocyanate compound having an ethylenically unsaturated bond and a blocking agent are stirred in a solvent at a temperature of about 0 to 200 ° C., and known separation and purification means such as concentration, filtration, extraction, crystallization, distillation, etc. are performed. It can obtain by separating using.
  • Another method for introducing a heat-crosslinkable functional group into an acrylic resin is to obtain a functional group that can react with the functional group and a heat-crosslinkable functional group on the functional group of the acrylic resin after obtaining the acrylic resin. It is the method of making the compound which has it react. For example, by reacting a glycidyl group of an ethylenically unsaturated monomer having a glycidyl group with a carboxyl group in an acrylic resin having a carboxyl group, an acrylic resin having a (meth) acryloyl group as a thermally crosslinkable functional group is obtained. Obtainable.
  • At least one kind of the above heat-crosslinkable functional group needs to be contained in the resin, and two or more kinds may be contained.
  • thermally crosslinkable functional groups when two or more types of thermally crosslinkable functional groups are contained, there is a preferable combination among the thermally crosslinkable functional groups.
  • This is a combination in which heat-crosslinkable functional groups are more likely to react with each other when heated. In this case, the effect of crosslinking is improved. For example, it is effective to use an oxetanyl group and a carboxyl group at the same time.
  • a t-butyl group becomes a carboxyl group when heated, a combination of an oxetanyl group and a t-butyl group is also effective.
  • a combination of a hydroxyl group, a blocked isocyanate group and an isocyanate group is also effective.
  • the combination of a hydroxyl group and a carboxyl group is most preferable because not only a strong film can be obtained by thermal crosslinking, but also in the alkali development step before thermal crosslinking, alkali developability is improved by the presence of carboxyl groups.
  • the glass transition temperature (hereinafter abbreviated as Tg) is 50 ° C. by selecting the ethylenically unsaturated monomer to be used.
  • the above acrylic resin can be obtained. It is possible to control the Tg of the acrylic resin by appropriately selecting the ethylenically unsaturated monomer to be used within a range that does not affect other physical properties. Since Tg of the acrylic resin directly affects the heat resistance of the color filter, when this Tg is less than 50 ° C. and does not have a thermally crosslinkable functional group, a color change at high temperature, that is, poor heat resistance occurs.
  • the Tg of the acrylic part is more preferably 70 ° C. or higher.
  • the upper limit of Tg is not particularly limited, but if it exceeds 150 ° C., there may be practical problems in workability and film-forming properties, and therefore it is preferably less than 150 ° C.
  • the Tg of the acrylic resin of the present invention indicates a value calculated from the Tg of the homopolymer of each of the ethylenically unsaturated monomers to be copolymerized by the Fox formula shown below.
  • W1 to Wn represent the weight fraction of the monomer used
  • Tg1 to Tgn represent the glass transition temperature of the monomer homopolymer (unit is absolute temperature “K”).
  • Tg (glass transition temperature) of the homopolymer of the main monomer used for calculation is illustrated below.
  • the glass transition temperature of the vinyl polymer portion obtained by radical polymerization of an ethylenically unsaturated monomer synthesized using 90 parts by weight of methyl methacrylate and 10 parts by weight of ethyl acrylate is 86. 8 ° C.
  • the ethylenically unsaturated monomer having a high homopolymer Tg in the copolymer composition.
  • the ethylenically unsaturated monomers the following are high in Tg and are effective for increasing the Tg of the acrylic resin.
  • Methyl methacrylate 105 ° C (378K) t-Butyl methacrylate: 107 ° C (380K) Methacrylic acid: 130 ° C (403K) Acrylic acid: 106 ° C (379K) 3- (Methacryloyloxymethyl) 3-ethyloxetane: 105 ° C.
  • ethylenically unsaturated monomer examples include (meth) acrylic acid esters, crotonic acid esters, vinyl esters, maleic acid diesters, Preference is given to fumaric acid diesters, itaconic acid diesters, (meth) acrylamides, vinyl ethers, esters of vinyl alcohol, styrenes, (meth) acrylonitrile and the like.
  • vinyl monomers include the following compounds.
  • Examples of (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate , Isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, 2- (meth) acrylic acid 2- Ethylhexyl, t-octyl (meth) acrylate, dodecyl (meth) acrylate, octadecyl (meth) acrylate, acetoxyethyl (meth) acrylate, phenyl (meth) acrylate, 2-methoxyethyl (me
  • crotonates examples include butyl crotonate and hexyl crotonate.
  • vinyl esters examples include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl methoxyacetate, vinyl benzoate, and the like.
  • maleic acid diesters examples include dimethyl maleate, diethyl maleate, and dibutyl maleate.
  • fumaric acid diesters examples include dimethyl fumarate, diethyl fumarate, and dibutyl fumarate.
  • itaconic acid diesters examples include dimethyl itaconate, diethyl itaconate, and dibutyl itaconate.
  • Examples of (meth) acrylamides include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, Nn -Butylacrylic (meth) amide, Nt-butyl (meth) acrylamide, N-cyclohexyl (meth) acrylamide, N- (2-methoxyethyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N , N-diethyl (meth) acrylamide, N-phenyl (meth) acrylamide, N-benzyl (meth) acrylamide, (meth) acryloylmorpholine, diacetone acrylamide and the like.
  • Examples of vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether.
  • Examples of styrenes include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropyl styrene, butyl styrene, hydroxy styrene, methoxy styrene, butoxy styrene, acetoxy styrene, chlorostyrene, dichlorostyrene, bromostyrene, chloromethyl
  • Examples thereof include styrene, hydroxystyrene protected with a group that can be deprotected by an acidic substance (for example, t-Boc and the like), methyl vinylbenzoate, and ⁇ -methylstyrene.
  • the resin (B) having a cationic group in the side chain known methods such as anion polymerization, living anion polymerization, cation polymerization, living cation polymerization, free radical polymerization, and living radical polymerization can be used. Of these, free radical polymerization or living radical polymerization is preferred.
  • a polymerization initiator for example, an azo compound and an organic peroxide can be used.
  • azo compounds include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane 1-carbonitrile), 2 , 2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2'-azobis (2-methylpropionate) 4,4′-azobis (4-cyanovaleric acid), 2,2′-azobis (2-hydroxymethylpropionitrile), or 2,2′-azobis [2- (2-imidazolin-2-yl ) Propane] and the like.
  • organic peroxides examples include benzoyl peroxide, t-butyl perbenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di (2-ethoxyethyl) peroxy
  • examples thereof include dicarbonate, t-butyl peroxyneodecanoate, t-butyl peroxybivalate, (3,5,5-trimethylhexanoyl) peroxide, dipropionyl peroxide, and diacetyl peroxide.
  • These polymerization initiators can be used alone or in combination of two or more.
  • the reaction temperature is preferably 40 to 150 ° C., more preferably 50 to 110 ° C.
  • the reaction time is preferably 3 to 30 hours, more preferably 5 to 20 hours.
  • the atom transfer radical polymerization method using an organic halide or a sulfonyl halide compound as an initiator and a transition metal complex as a catalyst is applicable to a wide range of monomers, and has a polymerization temperature applicable to existing equipment. It is preferable in that it can be adopted.
  • the atom transfer radical polymerization method can be carried out by the methods described in References 1 to 8 below.
  • an organic solvent for the polymerization is not particularly limited.
  • the organic solvent is not particularly limited.
  • the amount of the ammonium base present in the resin (B) having a cationic group in the side chain is not particularly limited, but the ammonium salt value of the resin is preferably 10 to 200 mgKOH / g, 20 to More preferably, it is 130 mgKOH / g.
  • the ammonium salt value is less than 10 mgKOH / g, the ratio of the anionic dye (C) to be reacted is reduced, so that the coloring power is lowered, and more salt-forming compound (D) is required in the resist material. Therefore, the binder resin, the curable resin, or the like originally added to the resist material is reduced, and the glass adhesion of the resist film may be deteriorated or the coating film resistance of the resist film may be deteriorated.
  • the solvent solubility of the salt-forming compound (D) deteriorates and precipitates as a foreign substance in the resist material.
  • the preferable content of the structural unit having a quaternary ammonium base is 4 to 74% by weight in a total of 100% by weight of the structural units constituting the resin, A more preferred range is 8 to 48% by weight.
  • the molecular weight of the resin (B) having a cationic group in the side chain used in the present invention is not particularly limited, but the polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography (GPC) is 1, It is preferably from 000 to 500,000, more preferably from 1,000 to 80,000, still more preferably from 2,000 to 20,000, and most preferably from 3,000 to 15,000.
  • GPC gel permeation chromatography
  • the resin (B) having a cationic group in the side chain to be used has a property of being dissolved in a solvent widely used in the color filter coloring composition. Thereby, the coating film without a foreign material generation
  • the anionic dye (C) may be a colored compound having an anionic group that is ionically bonded to the cationic group described above.
  • a coloring compound is not particularly limited as long as it has a carboxylic acid group, a sulfonic acid group, a phenolic hydroxyl group, a phosphoric acid group, or a metal salt thereof in the molecule, and an organic solvent or developer. Can be appropriately selected in consideration of all the required performance such as solubility in water, salt-forming property, absorbance, interaction with other components in the composition, light resistance, heat resistance and the like.
  • anionic dye (C) examples include an anthraquinone anionic dye, a monoazo anionic dye, a disazo anionic dye, an oxazine anionic dye, an aminoketone anionic dye, a xanthene anionic dye, and a quinoline anion. Dyes, triphenylmethane anionic dyes and the like. Below, the specific example of the anionic dye which can be used for the synthesis
  • C.I. I. Direct Red 1, 2, 2: 1, 4, 5, 6, 7, 8, 10, 10: 1, 13, 14, 15, 16, 17, 18, 21, 22, 23, 24, 26, 26: 1, 28, 29, 31, 33, 33: 1, 34, 35, 36, 37, 39, 42, 43, 43: 1, 44, 46, 49, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 67, 67: 1, 68, 72, 72: 1, 73, 74, 75, 77, 78, 79, 81, 81: 1, 85, 86, 88, 89, 90, 97, 100, 101, 101: 1, 107, 108, 110, 114, 116, 117, 120, 121, 122, 122: 1, 124, 125, 127, 127: 1, 127: 2, 128, 129, 130, 132, 134, 135, 136, 137 138, 140, 141, 148, 149, 150, 152, 153, 154, 155, 156,
  • ⁇ As yellow dyes C.I. I. Acid Yellow 2, 3, 4, 5, 6, 7, 8, 9, 9: 1, 10, 11, 11: 1, 12, 13, 14, 15, 16, 17, 17: 1, 18, 20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40: 1, 41, 42, 42: 1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66, 67, 68, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 19 Etc.
  • C.I. Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44: 1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, 134, etc. can also be used.
  • C.I. I. Direct orange 1, 2, 3, 4, 5, 6, 7, 8, 10, 13, 17, 19, 20, 21, 24, 25, 26, 29, 29: 1, 30, 31, 32, 33, 43, 49, 51, 56, 59, 69, 72, 73, 74, 75, 76, 79, 80, 83, 84, 85, 87, 88, 90, 91, 92, 95, 96, 97, 98, 101, 102, 102: 1, 104, 108, 112, 114, etc. can also be used.
  • C.I. Direct Blue 1, 2, 3, 4, 6, 7, 8, 8: 1, 9, 10, 12, 14, 15, 16, 19, 20, 21, 21: 1, 22, 23, 25, 27, 29, 31, 35, 36, 37, 40, 42, 45, 48, 49, 50, 53, 54, 55, 58, 60, 61, 64, 65, 67, 79, 96, 97, 98: 1, 101, 106, 107, 108, 109, 111, 116, 122, 123, 124, 128, 129130, 130: 1, 132, 136, 138, 140, 145, 146, 149, 152, 153, 154, 156, 158, 158: 1, 164, 165, 166, 167, 168, 169, 170, 174, 177, 181, 184, 185, 188, 190, 192, 193, 206, 207, 209, 2 3,215,225,226,229,230,231,242,243,244,253,254,260,263 and the like
  • C.I. I. Direct violet 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 21, 22, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 51, 52, 54, 57, 58, 61, 62, 63, 64, 71, 72, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 93, 97, etc. can also be used.
  • C.I. I. Acid Green 2 3, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 22, 25, 25: 1, 27, 34, 36, 37, 38, 40, 41, 42, 44, 54, 55, 59, 66, 69, 70, 71, 81, 84, 94, 95 and the like.
  • the salt-forming compound (D) of the present invention is prepared by stirring or vibrating an aqueous solution in which a resin (B) having a cationic group in the side chain and an anionic dye (C) are dissolved, or cationic in the side chain. It can be easily obtained by mixing an aqueous solution of the resin (B) having a group and an aqueous solution of the anionic dye (C) under stirring or vibration. In the aqueous solution, the cationic group of the resin and the anionic group of the dye are ionized, these are ionically bonded, and the ion-bonded portion becomes water-insoluble and precipitates.
  • the salt composed of the counter anion of the resin and the counter cation of the acidic dye is water-soluble and can be removed by washing or the like.
  • the resin (B) having a cationic group in the side chain to be used and the anionic dye (C) only a single type or a plurality of types having different structures may be used.
  • a mixed solution of water and a water-soluble organic solvent may be used in order to dissolve the resin (B) having a cationic group in the side chain and an anionic dye.
  • the water-soluble organic solvent include methanol, ethanol, n-propanol, isopropanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, n-butanol, isobutanol, 2- (methoxymethoxy) ethanol, 2- Butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, ethylene glycol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene Glycol, propylene glycolic monomethyl ether acetate, dipropylene glycol,
  • the ratio of the resin (B) having a cationic group in the side chain and the anionic dye (C) is such that the molar ratio of the total cationic unit of the resin to the total anionic group of the anionic dye (C) is 10: 1.
  • the salt-forming compound (D) of the present invention can be suitably adjusted, and the range of 2: 1 to 1: 2 is more preferable.
  • the coloring composition for a color filter of the present invention can be used as a coloring composition for a color filter by further adding a pigment.
  • organic or inorganic pigments can be used alone or in combination of two or more.
  • the pigment is preferably a pigment having a high color developability and a high heat resistance, particularly a pigment having a high heat decomposition resistance, and an organic pigment is usually used.
  • an organic pigment is usually used.
  • the specific example of the organic pigment which can be used for the coloring composition for color filters is shown by a color index number.
  • red coloring composition for forming the red filter segment examples include C.I. I. Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 97, 122, 123, 146, 149, 150, 168, 169, 176, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 209, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 242, 246, 254, 255, 264, 268, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, Red pigments such as 286 or 287 can be used.
  • the red coloring composition includes C.I. I. Pigment Orange 36, 38, 43, 51, 55, 59, 61, 71, 73 or the like and / or C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169,
  • Examples of the green coloring composition for forming the green filter segment include C.I. I. Green pigments such as CI Pigment Green 7, 10, 36, 37, 58 can be used.
  • the green coloring composition includes C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171,
  • the blue coloring composition for forming the blue filter segment includes, for example, C.I. I. Pigment Blue 1, 1: 2, 1: 3, 2, 2: 1, 2: 2, 3, 8, 9, 10, 10: 1, 11, 12, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 18, 19, 22, 24, 24: 1, 53, 56, 56: 1, 57, 58, 59, 60, 61, 62, 64, etc. Can be used.
  • the blue coloring composition includes C.I. I. Purple violet pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50 can be used in combination.
  • cyan coloring compositions for forming cyan filter segments include C.I. I. Blue pigments such as CI Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16, and 81 can be used alone or in combination.
  • magenta colored composition for forming the magenta color filter segment examples include C.I. I. Pigment Violet 1, 19, C.I. I. Pigment Red 144, 146, 177, 169, 81, etc. Purple pigments and red pigments can be used alone or in combination. A yellow pigment can be used in combination with the magenta composition.
  • Inorganic pigments include titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine, bitumen, chromium oxide green, cobalt green, amber And synthetic iron black. Inorganic pigments are used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while maintaining a balance between saturation and lightness.
  • the pigment added to the coloring composition of the present invention is preferably refined by a salt milling process or the like in order to correspond to high transmittance and high contrast.
  • the primary particle diameter of the pigment is preferably 10 nm or more because of good dispersion in the colorant carrier.
  • a filter segment with high contrast can be formed, it is preferable that it is 80 nm or less. A particularly preferred range is 20 to 60 nm.
  • Salt milling is a machine that heats a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill. After kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water.
  • the water-soluble inorganic salt serves as a crushing aid, and the pigment is crushed using the high hardness of the inorganic salt during salt milling.
  • water-soluble inorganic salt sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price.
  • the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by weight, and most preferably 300 to 1000 parts by weight, based on the total weight of the pigment (100 parts by weight) in terms of both processing efficiency and production efficiency.
  • the water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used.
  • a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated.
  • the water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, based on the total weight of the pigment (100 parts by weight).
  • a resin When the salt is milled with a pigment, a resin may be added as necessary.
  • the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used.
  • the resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent.
  • the amount of resin used is preferably in the range of 5 to 200 parts by weight based on the total weight of the pigment (100 parts by weight).
  • the binder resin is one that disperses a colorant, particularly a salt-forming compound (D) and a pigment, or one that dyes and penetrates a salt-forming compound, and examples thereof include thermoplastic resins and thermosetting resins.
  • thermoplastic resin examples include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin.
  • thermosetting resin examples include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.
  • the binder resin is preferably a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.
  • the coloring composition for color filters of the present invention is in the form of an alkali development type colored resist material, it is preferable to use an alkali-soluble vinyl resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer.
  • alkali-soluble resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer examples include resins having an acidic group such as a carboxyl group or a sulfone group.
  • Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an ⁇ -olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer.
  • At least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.
  • an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.
  • an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain because it has an effect of improving the solvent resistance of the resist material.
  • Examples of the active energy ray-curable resin having an ethylenically unsaturated double bond include resins having an unsaturated ethylenic double bond introduced by the following methods (a) and (b).
  • Method (a) for example, a side chain epoxy group of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having an epoxy group and one or more other monomers is used. Then, the carboxyl group of the unsaturated monobasic acid having an unsaturated ethylenic double bond is subjected to an addition reaction, and the resulting hydroxyl group is reacted with a polybasic acid anhydride to convert the unsaturated ethylenic double bond and the carboxyl group into There is a way to introduce.
  • Examples of the unsaturated ethylenic monomer having an epoxy group include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 2-glycidoxyethyl (meth) acrylate, 3,4 epoxybutyl (meth) acrylate, And 3,4 epoxy cyclohexyl (meth) acrylates, and these may be used alone or in combination of two or more. From the viewpoint of reactivity with the unsaturated monobasic acid in the next step, glycidyl (meth) acrylate is preferred.
  • unsaturated monobasic acids include (meth) acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, ⁇ -haloalkyl of (meth) acrylic acid, alkoxyl, halogen, nitro, cyano-substituted products, etc.
  • a monocarboxylic acid etc. are mentioned. These may be used alone or in combination of two or more.
  • polybasic acid anhydride examples include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride and the like. These may be used alone or in combination of two or more.
  • a tricarboxylic acid anhydride such as trimellitic acid anhydride may be used as necessary, for example, by increasing the number of carboxyl groups.
  • the remaining anhydride group may be hydrolyzed using tetracarboxylic dianhydride such as pyromellitic dianhydride.
  • a side chain of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group and one or more other monomers for example, a side chain of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group and one or more other monomers.
  • an unsaturated ethylenic monomer having an epoxy group is added to a part of a carboxyl group to introduce an unsaturated ethylenic double bond and a carboxyl group.
  • Method (b) As the method (b), an unsaturated ethylenic monomer having a hydroxyl group is used, and an unsaturated monobasic acid monomer having another carboxyl group or another monomer is copolymerized. There is a method of reacting an isocyanate group of an unsaturated ethylenic monomer having an isocyanate group with a side chain hydroxyl group of the obtained copolymer.
  • Examples of the unsaturated ethylenic monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, glycerol
  • Examples thereof include hydroxyalkyl (meth) acrylates such as (meth) acrylate or cyclohexanedimethanol mono (meth) acrylate, and these may be used alone or in combination of two or more.
  • Polyether mono (meth) acrylates obtained by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide to the above hydroxyalkyl (meth) acrylate, (poly) ⁇ -valerolactone, (poly) ⁇ -caprolactone And / or (poly) ester mono (meth) acrylate added with (poly) 12-hydroxystearic acid or the like can also be used. From the viewpoint of suppressing foreign matter in the coating film, 2-hydroxyethyl (meth) acrylate or glycerol (meth) acrylate is preferable.
  • Examples of the unsaturated ethylenic monomer having an isocyanate group include 2- (meth) acryloyloxyethyl isocyanate or 1,1-bis [(meth) acryloyloxy] ethyl isocyanate, but are not limited thereto. Two or more types can be used in combination.
  • the weight average molecular weight (Mw) of the binder resin is preferably in the range of 10,000 to 100,000, more preferably in the range of 10,000 to 80,000 in order to disperse the colorant preferably.
  • the number average molecular weight (Mn) is preferably in the range of 5,000 to 50,000, and the value of Mw / Mn is preferably 10 or less.
  • the binder resin has an affinity for a colorant adsorbing group and a carboxyl group that acts as an alkali-soluble group during development, a colorant carrier, and a solvent from the viewpoint of dispersibility, penetrability, developability, and heat resistance of the pigment and salt-forming compound.
  • the balance between the aliphatic group and aromatic group acting as a functional group is important for the dispersibility, penetrability, developability and durability of the pigment and salt-forming compound, and a resin having an acid value of 20 to 300 mgKOH / g is used. It is preferable. When the acid value is less than 20 mgKOH / g, the solubility in the developer is poor and it is difficult to form a fine pattern. When it exceeds 300 mgKOH / g, no fine pattern remains.
  • the binder resin is preferably used in an amount of 30 parts by weight or more based on the total weight of the colorant (100 parts by weight) because of good film formability and various resistances. Since the colorant concentration is high and good color characteristics can be expressed, it is preferably used in an amount of 500 parts by weight or less.
  • the colorant is sufficiently dispersed and permeated in the colorant carrier, and is applied onto a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 ⁇ m.
  • An organic solvent can be included to facilitate the formation.
  • organic solvent examples include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl 1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m -Diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N Dimethylformamide, n
  • ethyl lactate propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether
  • glycol acetates such as acetate, aromatic alcohols such as benzyl alcohol, and ketones such as cyclohexanone.
  • propylene glycol monomethyl ether acetate is more preferable from the viewpoints of health and safety and low viscosity.
  • organic solvents may be used alone or in combination of two or more.
  • the mixed solvent in which two or more kinds are mixed preferably contains 65 to 95% by weight of the above-mentioned preferred organic solvent.
  • the organic solvent can adjust the colored composition to an appropriate viscosity to form a filter segment having a desired uniform film thickness, so that 800 to 4000 weights based on the total weight of the colorant (100 parts by weight). It is preferable to use in the amount of parts.
  • the colored composition of the present invention comprises a salt-forming compound (D) obtained by reacting a resin (B) having a cationic group in the side chain with an anionic dye (C), the binder resin and a solvent.
  • a pigment is further included in the colorant carrier, the pigment is preferably used together with a dispersing aid such as a dye derivative, and various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, a kneader, or an attritor are used. Then, the colored composition can be produced by finely dispersing.
  • the colored composition of the present invention can also be produced by mixing pigments, salt-forming compounds (D), and other colorants separately dispersed in a colorant carrier.
  • a dispersion aid such as a pigment derivative, a resin-type dispersant, and a surfactant can be appropriately used.
  • the dispersion aid is excellent in dispersion of the colorant and has a large effect of preventing reaggregation of the colorant after dispersion. Therefore, a dispersion composition is used to disperse the colorant in the colorant carrier using the dispersion aid. When used, a color filter having a high spectral transmittance can be obtained.
  • the salt-forming compound (D) is also expected to play a role as a pigment dispersion aid.
  • Examples of the dye derivative include a compound obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group which may have a substituent into an organic pigment, anthraquinone, acridone, or triazine.
  • JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469 and the like can be used. These may be used alone or in combination of two or more.
  • the blending amount of the pigment derivative is preferably 0.5 parts by weight or more, more preferably 1 part by weight or more, most preferably from the viewpoint of improving the dispersibility of the additive pigment, based on the total amount of the additive pigment (100 parts by weight). 3 parts by weight or more. From the viewpoint of heat resistance and light resistance, the total amount of the additive pigment is preferably 40 parts by weight or less, more preferably 35 parts by weight or less, based on the total amount (100 parts by weight).
  • the resin-type dispersant has a pigment-affinity part that has the property of adsorbing to the additive pigment and a part that is compatible with the colorant carrier, and adsorbs to the additive pigment to stabilize dispersion in the colorant carrier. It works.
  • resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts.
  • Water-soluble dispersants such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone Resin, water-soluble polymer, polyester, modified poly A acrylate system, an ethylene oxide / propylene oxide addition compound, a phosphate ester system, and the like are used. These may be used alone or in combination of two or more, but are not necessarily limited thereto. is not.
  • resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 170 manufactured by Big Chemie Japan.
  • Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate
  • Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate, and
  • the amount of the resin type dispersant or surfactant added is preferably 0.1 to 55 parts by weight, more preferably 0.1 to 45 parts by weight, based on the total amount of the added pigment (100 parts by weight). It is. When the blending amount of the resin-type dispersant or the surfactant is less than 0.1 parts by weight, it is difficult to obtain the added effect. When the blending amount is more than 55 parts by weight, the dispersion is adversely affected by the excessive dispersant. May have an effect.
  • the colored composition of the present invention can be used as a photosensitive colored composition for a color filter by further adding a photopolymerizable monomer and / or a photopolymerization initiator.
  • the photopolymerizable monomer of the present invention includes a monomer or oligomer that is cured by ultraviolet rays or heat to produce a transparent resin. These may be used alone or in combination of two or more.
  • the blending amount of the monomer is preferably 5 to 400 parts by weight based on the total weight of the colorant (100 parts by weight), and more preferably 10 to 300 parts by weight from the viewpoint of photocurability and developability. preferable.
  • Monomers and oligomers that are cured by ultraviolet rays or heat to produce transparent resins include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate , Cyclohexyl (meth) acrylate, ⁇ -carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglyme Diether ether di (meth) acrylate
  • the colored composition for a color filter of the present invention is a solvent development type or alkali development type colored resist material added with a photopolymerization initiator or the like when the composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method. It can be prepared in the form of
  • the blending amount when using the photopolymerization initiator is preferably 5 to 200 parts by weight based on the total amount of the colorant, and 10 to 150 parts by weight from the viewpoint of photocurability and developability. More preferred.
  • photopolymerization initiator examples include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1
  • Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as benzyl di
  • photopolymerization initiators can be used alone or in combination of two or more at any ratio as required.
  • These photopolymerization initiators are preferably 5 to 200 parts by weight based on the total amount of the colorant in the color filter coloring composition (100 parts by weight), and are 10 from the viewpoint of photocurability and developability. More preferably, it is ⁇ 150 parts by weight.
  • the coloring composition for a color filter of the present invention can contain a sensitizer.
  • Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, te
  • the blending amount when using the sensitizer is preferably 3 to 60 parts by weight based on the total weight (100 parts by weight) of the photopolymerization initiator contained in the colored composition. From the viewpoint of developability, the amount is more preferably 5 to 50 parts by weight.
  • the coloring composition of this invention can be made to contain the amine compound which has a function which reduces the dissolved oxygen.
  • amine compounds examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate.
  • examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.
  • a leveling agent In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the colored composition of the present invention.
  • the leveling agent dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable.
  • dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by Big Chemie.
  • dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie.
  • Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination.
  • the leveling agent content is preferably 0.003 to 0.5% by weight based on the total weight of the coloring composition (100% by weight).
  • a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, has a hydrophilic group, but has low solubility in water, and when added to a coloring composition, its surface tension decreases. Those with low performance are preferred. Furthermore, it is useful to have good wettability to the glass plate despite its low surface tension lowering ability, and those that can sufficiently suppress the chargeability in an added amount that does not cause defects in the coating film due to foaming are suitable. is there.
  • the leveling agent having these preferable characteristics include dimethylpolysiloxane having a polyalkylene oxide unit.
  • the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit. Dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
  • the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used.
  • Dimethylpolysiloxanes having polyalkylene oxide units are commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
  • ⁇ Anionic, cationic, nonionic or amphoteric surfactants can be supplementarily added to the leveling agent. Two or more surfactants may be used as a mixture.
  • Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.
  • Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.
  • the coloring composition of this invention may contain the hardening
  • curing agent phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine curing agent are preferable.
  • curing accelerator examples include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl).
  • amine compounds for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl).
  • the colored composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity of the composition over time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.
  • Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned.
  • the storage stabilizer can be used in an amount of 0.1 to 10 parts by weight based on the total amount of the colorant (100 parts by weight).
  • adhesion improver examples include vinyl silanes such as vinyl tris ( ⁇ -methoxyethoxy) silane, vinyl ethoxy silane and vinyl trimethoxy silane, (meth) acryl silanes such as ⁇ -methacryloxypropyl trimethoxy silane, ⁇ - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) methyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, N- ⁇ (aminoethyl) ⁇ -aminopropyltrime
  • the coloring composition of the present invention is mixed with coarse particles of 5 ⁇ m or more, preferably coarse particles of 1 ⁇ m or more, more preferably 0.5 ⁇ m or more and coarse particles by means of centrifugation, sintered filter, membrane filter or the like. It is preferable to remove dust.
  • a coloring composition does not contain a particle
  • the color filter of this invention comprises the filter segment formed using the coloring composition for color filters of this invention.
  • Examples of the color filter include those having a red filter segment, a green filter segment, and a blue filter segment, or those having a magenta filter segment, a cyan filter segment, and a yellow filter segment.
  • glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali aluminoborosilicate glass, and resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate are used.
  • resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate are used.
  • a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
  • the color filter of the present invention can be produced by a printing method or a photolithography method.
  • filter segments by printing methods allows patterning by simply printing and drying the colored composition prepared as a printing ink, making it a low cost and excellent mass productivity as a color filter manufacturing method. Yes. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Further, it is important to control the fluidity of the ink on the printing press, and the viscosity of the ink can be adjusted with a dispersant or extender.
  • the colored composition prepared as a solvent developing type or alkali developing type colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. By the method, it is applied so that the dry film thickness is 0.2 to 5 ⁇ m. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.
  • an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used.
  • an antifoamer and surfactant can also be added to a developing solution.
  • a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Then, ultraviolet exposure can be performed.
  • the color filter of the present invention can be produced by an electrodeposition method, a transfer method or the like in addition to the above method, but the colored composition of the present invention can be used in any method.
  • the electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles.
  • the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.
  • a black matrix can be formed in advance before forming each color filter segment on a transparent substrate or a reflective substrate.
  • a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto.
  • a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment may be formed.
  • an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention as necessary.
  • the binder resin, the refined pigment, the resin (B) having a cationic group in the side chain, and the production method of the salt-forming compound (D) used in Examples and Comparative Examples will be described.
  • the methoxypropyl acetate was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight.
  • the binder resin solution 1 was prepared by adding.
  • Mw weight average molecular weight of the binder resin was measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
  • the reaction was further carried out at 100 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour.
  • the inside of the container is replaced with air, and 0.5 part of trisdimethylaminophenol and 0.1 part of hydroquinone are put into 9.3 parts of acrylic acid (100% of glycidyl group) and the container is placed at 120 ° C.
  • the reaction was continued for 6 hours, and the reaction was terminated when the solid content acid value reached 0.5 to obtain a copolymer solution.
  • a binder resin solution 4 was prepared.
  • the weight average molecular weight (Mw) was 19000.
  • the average primary particle diameter of the pigment was measured using a transmission electron microscope (“JEM-1200EX” manufactured by JEOL Ltd.) by measuring the primary particle diameter of all pigment particles in the observation sample at 50,000 times. Average values were used.
  • the major axis and the minor axis were measured, and the value obtained by (major axis + minor axis) / 2 was defined as the particle diameter.
  • P-2 Dioxazine-based purple pigment C.I. I. 120 parts of Pigment Violet 23 (“Fast Violet RL” manufactured by Clariant), 1600 parts of ground sodium chloride, and 100 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 90 ° C. for 18 hours. The mixture was poured into 5000 parts of warm water, stirred at a high speed mixer for about 1 hour while being heated to about 70 ° C. to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It was dried to obtain 118 parts of purple fine pigment (P-2). The average primary particle diameter of the obtained pigment was 26.4 nm.
  • Red fine pigment (P-3) Diketopyrrolopyrrole red pigment C.I. I. 200 parts of Pigment Red 254 (“IRGAZIN RED 2030” manufactured by Ciba Japan Co., Ltd.), 1400 parts of ground sodium chloride and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. The mixture was poured into 8000 parts of warm water, heated to about 80 ° C., stirred with a high speed mixer for about 2 hours to form a slurry, filtered and washed repeatedly to remove salt and solvent, then at 85 ° C. for 24 hours. Drying gave 190 parts of red fine pigment (P-3). The average primary particle diameter of the obtained pigment was 24.8 nm.
  • Red fine pigment (P-4) Red pigment C.I. I. 200 parts of Pigment Red 242 (“NOVOPERM SCARLET 4RF” manufactured by Clariant), 1400 parts of ground sodium chloride, and 360 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. The mixture is poured into 8000 parts of warm water, stirred for 2 hours with a high speed mixer while being heated to about 80 ° C. to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then dried at 85 ° C. for 24 hours. 190 parts of red fine pigment (P-4) were obtained. The average primary particle diameter of the obtained pigment was 28.5 nm.
  • the weight average molecular weight (Mw) of the resin having a cationic group in the side chain was measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
  • the ammonium salt value of the resin (B) having a cationic group in the side chain was determined by titrating with a 0.1N silver nitrate aqueous solution using 5% potassium chromate aqueous solution as an indicator, and then the equivalent of potassium hydroxide. It is the converted value and indicates the ammonium salt value of the solid content.
  • Resin B-18 having a cationic group in the side chain was synthesized by synthesizing a carboxyl group-containing acrylic resin in the same manner as in Production Example 1 except that a monomer other than GMA (glycidyl methacrylate) shown in Table 1 was used. By reacting the glycidyl group of GMA with the glycidyl group of GMA, Resin B-18 having a heat-crosslinkable group (methacryloyl group) and a cationic group in the side chain was obtained. The procedure is shown below.
  • MMA Methyl methacrylate (105 ° C) n-BMA: n-butyl methacrylate (20 ° C) 2-EHMA: 2-ethylhexyl methacrylate (-10 ° C) 2-EHA: 2-ethylhexyl acrylate (-85 ° C) CHMA: cyclohexyl methacrylate (66 ° C) i-BuMA: Isobutyl methacrylate (48 ° C) HEMA: hydroxyethyl methacrylate (55 ° C) HEA: hydroxyethyl acrylate (-15 ° C) 4HBA: 4-hydroxybutyl acrylate (-80 ° C) MAA: Methacrylic acid (130 ° C) AA: Acrylic acid (106 ° C) OXMA: 3- (methacryloyloxymethyl) 3-ethyloxetane (ETERRNACOLL OXMA (manufactured by Ube Industries)) (
  • Tg in Table 1 is a value calculated using the above formula.
  • the value of the glass transition temperature of MOI-BM in Production Example 17 was the value of 2-isocyanatoethyl methacrylate instead.
  • Production Example 18 is the value of Resin B-18 ′ before being modified with glycidyl methacrylate.
  • the resin B-1 having a cationic group in the side chain of 51 parts is added to 2000 parts of water, sufficiently mixed with stirring, and then heated to 60 ° C.
  • 10 parts of C.I. in 90 parts of water 10 parts of C.I. in 90 parts of water.
  • An aqueous solution in which acid red candy 289 is dissolved is prepared, and the resulting solution is added dropwise to the resin solution. After dropping, the mixture is stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.
  • salt-forming compounds D-5 to 17, 19 to 23, and 25 to 35 were produced in the same manner as in Production Example 25 except that the resin and dye having a cationic group in the side chain were changed to those shown in Table 2. did.
  • Salt-forming compound (H-1) In the following procedure, C.I. I. A salt-forming compound (H-1) consisting of Acid Red 289 and distearyldimethylammonium chloride (Coatamine D86P) was produced.
  • Cotamine D86P 11.5 parts of Cotamine D86P is added to 2000 parts of a 10% aqueous sodium hydroxide solution, sufficiently stirred and mixed, and then heated to 60 ° C.
  • 10 parts of C.I. in 90 parts of water 10 parts of C.I. in 90 parts of water.
  • An aqueous solution in which acid red candy 289 is dissolved is prepared and added dropwise to the previous solution little by little. After dropping, the mixture is stirred at 60 ° C. for 120 minutes to sufficiently react. In order to confirm the end point of the reaction, it was judged that a salt-forming compound was obtained with the reaction solution dropped onto the filter paper and the point where the bleeding disappeared as the end point.
  • a salt-forming compound (H-2) of acid red 52 and coatamine 24P was obtained.
  • Example 1 (Preparation of blue coloring composition (DB-1)) The following mixture was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 ⁇ m. A pigment dispersion (DB-1) was produced by filtration using a filter.
  • Salt-forming compound (D-1) 4.0 parts Fine pigment (P-1) 7.0 parts Binder resin solution 1 40.0 parts Cyclohexanone 10.0 parts Propylene glycol monomethyl ether acetate (PGMAC) 38.0 parts Resin 1.0 part of dispersant ("EFKA4300" manufactured by Ciba Japan)
  • Examples 2 to 49, Comparative Examples 1 to 9 (Blue coloring composition (DB-2 to 31, DB-50 to 52), purple coloring composition (DB-32, 33, DB-53, 54), red coloring composition (DB-34 to 49, DB- 55-58))
  • a colored composition (DB-2 to 58) was produced in the same manner as in Example 1 except that the salt-forming compound and the finer pigment were changed to the compositions shown in Table 3.
  • the obtained colored compositions (DB-1 to 60) were subjected to the following methods for evaluating the heat resistance of the coating film, the foreign matter test, and the storage stability of the colored composition with time. The results of the test are shown in Table 3.
  • the coloring composition (DB-1 to 60) is applied on a glass substrate of 100 mm ⁇ 100 mm and 1.1 mm thickness using a spin coater, then dried at 70 ° C. for 20 minutes, and then at 220 ° C. for 30 minutes.
  • the coated substrate was prepared by heating and allowing to cool.
  • the coating film substrate thus prepared was subjected to heat treatment at 220 ° C., and the spin coater coating rotation speed was adjusted so that the film thickness was 2.0 ⁇ m.
  • the chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 230 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ⁇ Eab * was determined.
  • ⁇ Eab * ⁇ ((L * (2)-L * (1)) 2 + (a * (2)-a * (1)) 2 + (b * (2)-b * (1)) 2 ) If ⁇ Eab * is less than 3.0, there is no practical problem as a color filter. ⁇ Eab is more preferably 1.5 or less, and most preferably 1.0 or less.
  • a test substrate was prepared with the colored composition (DB-1 to 60) immediately after preparation, and the evaluation was performed by counting the number of particles. First, a colored composition is applied on a 100 mm ⁇ 100 mm, 1.1 mm thick transparent glass substrate with a spin coater so that the film thickness after drying is about 2.0 ⁇ m, and heated in an oven at 230 ° C. for 20 minutes. A test substrate was obtained.
  • AR289 C.I. I. Acid Red 289 AR52: C.I. I. Acid Red 52
  • the resin having a quaternary ammonium salt and a thermally crosslinkable functional group or an acrylic resin satisfying at least one of Tg of 50 ° C. or higher has good heat resistance, and ⁇ Eab is It was 3.0 or less. Moreover, it was excellent in storage stability, and the coating film foreign matter was in a range that can be used as a color filter.
  • the heat-crosslinkable functional groups contained in the resin having a cationic group are a hydroxyl group and a carboxyl group, and therefore, heat resistance is further improved.
  • ⁇ Eab was 1.5 or less.
  • Examples 12 and 27 are acrylic resins having a glass transition temperature of 50 ° C. or higher, and thus have very good heat resistance, and ⁇ Eab was 1.0 or less.
  • the heat-crosslinkable functional group contained in the resin having a cationic group is a hydroxyl group, and is an acrylic resin having a glass transition temperature of 50 ° C. or higher. Therefore, the heat resistance is very good.
  • ⁇ Eab was 1.0 or less.
  • Comparative Examples 10 and 11 were not only poor in heat resistance but also poor in storage stability with time, and the coating film foreign matter test was slightly inferior.
  • Example 50 (Preparation of blue photosensitive coloring composition (R-1)) The following mixture was stirred and mixed to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare an alkali developing resist material R-1.
  • Examples 51 to 101, Comparative Examples 12 to 22 (Blue photosensitive coloring composition (R-2 to 34, R-53 to 55, R-62, 63), Purple photosensitive coloring composition (R-35 to 36, R-56 to 57), Red photosensitive property Coloring composition (production of R-37 to 52, R-58 to 61))
  • Alkaline development type photosensitive coloring compositions (R-2 to 63) were prepared in the same manner as in Example 50 except that the coloring composition and the binder resin solution were changed to the coloring compositions shown in Table 4.
  • a test substrate was prepared using the photosensitive coloring composition (R-1 to 63) immediately after preparation, and the evaluation was performed by counting the number of particles.
  • a photosensitive coloring composition was applied on a 100 mm ⁇ 100 mm, 1.1 mm thick transparent glass substrate with a spin coater so that the film thickness after drying was about 2.0 ⁇ m, dried at 70 ° C. for 20 minutes, UV exposure is performed with an integrated light quantity of 150 mJ / cm 2 using an ultrahigh pressure mercury lamp through a photomask having a stripe-shaped opening having a width of 100 ⁇ m, and unexposed with a 0.05% potassium hydroxide aqueous solution containing a surfactant.
  • the part was washed off and developed, and placed in a hot air oven at 230 ° C. for 20 minutes to form a stripe pattern having a width of 100 ⁇ m on the substrate to obtain a test substrate. Then, surface observation was performed using a metal microscope “BX60” manufactured by Olympus System (magnification is 500 times), and the number of particles that can be observed in any five visual fields by transmission was counted and evaluated according to the following criteria. did. In the evaluation results, ⁇ and ⁇ are good with a small number of foreign matters, ⁇ is a level where there is a large number of foreign matters, but there is no problem in use, and ⁇ is a state where it cannot be used because uneven coating due to foreign matters occurs. Equivalent to.
  • Glass adhesion test method Evaluation was performed by forming a test substrate in the same procedure as the coating film foreign matter test and confirming the chemical resistance. The obtained test substrate was immersed in a 5% aqueous sodium hydroxide solution at 25 ° C. for 30 minutes, and the adhesion to the glass before and after immersion was evaluated in three stages by visual observation.
  • a salt-forming compound (D) obtained by reacting a resin (B) having a cationic group in the side chain with an anionic dye (C), and the cationic group The resin having a quaternary ammonium salt and containing a heat-crosslinkable functional group or an acrylic resin satisfying at least one of Tg of 50 ° C. or higher has good heat resistance, and ⁇ Eab is It was 3.0 or less. Moreover, it was excellent in storage stability, the coating-film foreign material was in the range which can be used as a color filter, and it was a result with favorable glass adhesiveness, solvent resistance, and alkali developability.
  • Examples 62 to 67, 78 to 82, 88, 92 and 96 since the thermally crosslinkable functional groups contained in the resin having a cationic group are a hydroxyl group and a carboxyl group, the heat resistance is further improved.
  • ⁇ Eab was 1.5 or less.
  • Examples 64 and 79 were acrylic resins having a glass transition temperature of 50 ° C. or higher, and thus had very good heat resistance, and ⁇ Eab was 1.0 or less.
  • the heat-crosslinkable functional group contained in the resin having a cationic group is an acrylic resin having a hydroxyl group and a glass transition temperature of 50 ° C. or higher, so that the heat resistance is very good.
  • ⁇ Eab was 1.0 or less.
  • Comparative Examples 21 and 22 were not only poor in heat resistance but also poor in storage stability over time, glass adhesion and solvent resistance, and the coating film foreign matter test was slightly inferior.
  • a red photosensitive coloring composition, a blue photosensitive coloring composition and a green photosensitive coloring composition used for the preparation of a color filter were prepared.
  • red photosensitive coloring composition (RR-1) preparation of red photosensitive coloring composition (RR-1)
  • RR-1 preparation of red photosensitive coloring composition
  • Red pigment (CI Pigment Red 254) 9.6 parts Red Pigment (CI Pigment Red 177) 2.4 parts Resin-type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Binder resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts Subsequently, a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to obtain a red photosensitive coloring composition (RR). -1) was produced.
  • Red coloring composition 42.0 parts Binder resin solution 1 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a blue photosensitive coloring composition (RB-1).
  • green photosensitive coloring composition (RG-1) A mixture having the following composition was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm.
  • a green colored composition (DG-1) was prepared by filtration through a 0.0 ⁇ m filter.
  • Green pigment (CI Pigment Green 58) 12.0 parts Resin-type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 parts Binder resin solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1.0 ⁇ m filter to prepare a green photosensitive coloring composition (RG-1).
  • Green coloring composition (DG-1) 34.0 parts Binder resin solution 1 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907" 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 45.1 parts
  • the coating was irradiated with 300 mJ / cm 2 of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water. Formed.
  • a blue filter segment is formed so that the film thickness of the blue photosensitive coloring composition (R-2) of the present invention is 2.0 ⁇ m, and then the green photosensitive coloring composition (RG-1) is formed. ) To form a green color filter segment to obtain a color filter.
  • red photosensitive coloring composition (R-47), blue photosensitive coloring composition (RB-1), and green photosensitive coloring composition (RG-1) of the present invention a color filter Got.
  • the heat resistance of the color filter, the foreign matter test, the adhesion to a transparent substrate such as glass, the solvent resistance, and the alkali developability are improved and preferably used. I was able to.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition colorée pour filtre coloré et un filtre coloré qui comprend un agent colorant (A), une résine liante et un solvant organique, ladite composition colorée étant caractérisée en ce qu'elle contient un composé formant un sel produit par réaction d'une résine acrylique comportant un groupe cationique et un groupe fonctionnel thermiquement réticulable en tant que groupe de chaîne latérale avec un colorant anionique et/ou un composé formant un sel produit par réaction d'une résine acrylique comportant un groupe cationique en tant que groupe de chaîne latérale et ayant une température de transition vitreuse de 50°C ou plus, avec un colorant anionique.
PCT/JP2012/080601 2011-11-30 2012-11-27 Composition colorée pour filtre coloré, et filtre coloré WO2013080964A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201280059244.6A CN103959109B (zh) 2011-11-30 2012-11-27 滤色器用着色组合物及滤色器
KR1020147015898A KR102004436B1 (ko) 2011-11-30 2012-11-27 컬러 필터용 착색 조성물, 및 컬러 필터

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011261667A JP6205679B2 (ja) 2011-07-07 2011-11-30 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2011-261667 2011-11-30

Publications (1)

Publication Number Publication Date
WO2013080964A1 true WO2013080964A1 (fr) 2013-06-06

Family

ID=48536590

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/080601 WO2013080964A1 (fr) 2011-11-30 2012-11-27 Composition colorée pour filtre coloré, et filtre coloré

Country Status (4)

Country Link
KR (1) KR102004436B1 (fr)
CN (1) CN103959109B (fr)
TW (1) TWI504691B (fr)
WO (1) WO2013080964A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018024749A (ja) * 2016-08-09 2018-02-15 Jsr株式会社 着色剤、着色組成物、着色硬化膜、表示素子、固体撮像素子、化合物及び重合体
WO2019052845A1 (fr) 2017-09-14 2019-03-21 Evonik Röhm Gmbh Polymère et forme pharmaceutique avec propriétés de libération prolongée et résistance à l'influence de l'éthanol
JP2020091489A (ja) * 2014-12-24 2020-06-11 株式会社Ｄｎｐファインケミカル 色材分散液、カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置
JP2020187157A (ja) * 2019-05-10 2020-11-19 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104725560B (zh) * 2015-03-27 2017-03-15 江苏博砚电子科技有限公司 一种含染料丙烯酸树脂及其制备方法和应用
CN109564384B (zh) * 2016-08-01 2022-09-20 东洋油墨Sc控股株式会社 感光性着色组合物及彩色滤光片
WO2018110097A1 (fr) * 2016-12-14 2018-06-21 昭和電工株式会社 Composition de résine pour filtres colorés, son procédé de fabrication, et filtre coloré
KR102349145B1 (ko) * 2018-03-02 2022-01-10 동우 화인켐 주식회사 착색 감광성 수지 조성물, 이를 사용하여 제조된 컬러필터, 및 상기 컬러필터를 포함하는 표시장치
CN110850679B (zh) * 2018-08-21 2022-05-03 北京鼎材科技有限公司 高透射高溶解性的大分子染料，彩色光敏树脂组合物及彩色滤光片
CN111234094B (zh) * 2018-11-28 2022-06-21 北京鼎材科技有限公司 一种改性染料、包含其的光敏树脂组合物及用途

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004292508A (ja) * 2003-03-25 2004-10-21 Toppan Printing Co Ltd 着色組成物及び感光性着色組成物及びカラーフィルタ
JP2008138037A (ja) * 2006-11-30 2008-06-19 Toppan Printing Co Ltd インクジェット用インクおよびそれを用いたインクジェット法カラーフィルタ
JP2010191358A (ja) * 2009-02-20 2010-09-02 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物およびカラーフィルタ
JP2012032754A (ja) * 2010-06-30 2012-02-16 Fujifilm Corp 着色硬化性組成物、カラーフィルタ、その製造方法、固体撮像素子、液晶表示装置、および色素多量体

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05333207A (ja) 1992-05-29 1993-12-17 Nippon Kayaku Co Ltd カラーフィルター
JPH0675375A (ja) 1992-08-26 1994-03-18 Sony Corp カラーレジスト材料
JP3736221B2 (ja) 1998-08-28 2006-01-18 凸版印刷株式会社 カラーフィルターおよびこれを備えた液晶表示装置
JP4281154B2 (ja) 1999-06-11 2009-06-17 凸版印刷株式会社 感光性着色樹脂組成物及びカラーフィルター
JP4199580B2 (ja) 2003-04-07 2008-12-17 オリヱント化学工業株式会社 酸性染料のカチオン交換に用いる４級アンモニウム塩および造塩染料
JP4785379B2 (ja) 2004-05-12 2011-10-05 Ｄｉｃ株式会社 結晶性水性着色材料及びその製造方法
JP5694654B2 (ja) * 2009-09-09 2015-04-01 富士フイルム株式会社 インク組成物、インクセット、および画像形成方法
KR101533669B1 (ko) * 2009-12-01 2015-07-03 토요잉크Sc홀딩스주식회사 컬러 필터용 청색 착색 조성물, 컬러 필터 및 컬러 디스플레이
TWI443458B (zh) * 2010-04-21 2014-07-01 Toyo Ink Sc Holdings Co Ltd 彩色濾光片用紅色著色組成物及彩色濾光片
KR20120002453A (ko) * 2010-06-30 2012-01-05 후지필름 가부시키가이샤 착색 경화성 조성물, 컬러필터, 그 제조 방법, 고체 촬상 소자, 액정 표시 장치, 및 색소 다량체

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004292508A (ja) * 2003-03-25 2004-10-21 Toppan Printing Co Ltd 着色組成物及び感光性着色組成物及びカラーフィルタ
JP2008138037A (ja) * 2006-11-30 2008-06-19 Toppan Printing Co Ltd インクジェット用インクおよびそれを用いたインクジェット法カラーフィルタ
JP2010191358A (ja) * 2009-02-20 2010-09-02 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物およびカラーフィルタ
JP2012032754A (ja) * 2010-06-30 2012-02-16 Fujifilm Corp 着色硬化性組成物、カラーフィルタ、その製造方法、固体撮像素子、液晶表示装置、および色素多量体

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020091489A (ja) * 2014-12-24 2020-06-11 株式会社Ｄｎｐファインケミカル 色材分散液、カラーフィルタ用感光性着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置
JP2018024749A (ja) * 2016-08-09 2018-02-15 Jsr株式会社 着色剤、着色組成物、着色硬化膜、表示素子、固体撮像素子、化合物及び重合体
WO2019052845A1 (fr) 2017-09-14 2019-03-21 Evonik Röhm Gmbh Polymère et forme pharmaceutique avec propriétés de libération prolongée et résistance à l'influence de l'éthanol
JP2020187157A (ja) * 2019-05-10 2020-11-19 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
JP7226074B2 (ja) 2019-05-10 2023-02-21 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ

Also Published As

Publication number Publication date
TWI504691B (zh) 2015-10-21
TW201343806A (zh) 2013-11-01
KR20140100519A (ko) 2014-08-14
CN103959109B (zh) 2016-05-04
KR102004436B1 (ko) 2019-07-26
CN103959109A (zh) 2014-07-30

Similar Documents

Publication Publication Date Title
JP6205679B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP4873101B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6922247B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
WO2013080964A1 (fr) Composition colorée pour filtre coloré, et filtre coloré
JP5573417B2 (ja) カラーフィルタ用青色着色組成物、およびカラー固体撮像素子に用いるカラーフィルタ
JP6264854B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP5659918B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP5853731B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6958128B2 (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP5611099B2 (ja) カラーフィルタ用青色着色組成物、およびカラーフィルタ
JP5736932B2 (ja) カラーフィルタ用赤色着色組成物、およびカラーフィルタ
JP2012032770A (ja) カラーフィルタ用青色着色組成物、およびカラーフィルタ
JP2017198815A (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP6645335B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6733525B2 (ja) カラーフィルタ用感光性着色組成物およびカラーフィルタ
JP6911604B2 (ja) カラーフィルタ用着色剤、カラーフィルタ用着色組成物及びカラーフィルタ
JP2012013866A (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP2018155843A (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP5998781B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6728928B2 (ja) カラーフィルタ用着色組成物、およびカラーフィルタ
JP6939438B2 (ja) カラーフィルタ用着色組成物、及びカラーフィルタ
JP7484204B2 (ja) カラーフィルタ用着色組成物及びカラーフィルタ
JP2019081863A (ja) 感光性オリゴマー、その製造方法、感光性オリゴマーを用いたカラーフィルター用感光性着色組成物
KR101630454B1 (ko) 착색 조성물, 컬러 필터 및 컬러 액정 표시 소자
JP2018066778A (ja) カラーフィルタ用着色組成物およびカラーフィルタ

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201280059244.6

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12853155

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20147015898

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 12853155

Country of ref document: EP

Kind code of ref document: A1