WO2012117965A1 - Composition de pigment pour filtre coloré, composition colorée et filtre coloré - Google Patents

Composition de pigment pour filtre coloré, composition colorée et filtre coloré Download PDF

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Publication number
WO2012117965A1
WO2012117965A1 PCT/JP2012/054573 JP2012054573W WO2012117965A1 WO 2012117965 A1 WO2012117965 A1 WO 2012117965A1 JP 2012054573 W JP2012054573 W JP 2012054573W WO 2012117965 A1 WO2012117965 A1 WO 2012117965A1
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pigment
parts
composition
group
formula
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PCT/JP2012/054573
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English (en)
Japanese (ja)
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裕介 飯田
太郎 室星
雅之 藤木
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東洋インキＳｃホールディングス株式会社
トーヨーケム株式会社
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Publication of WO2012117965A1 publication Critical patent/WO2012117965A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0039—Mixtures of diketopyrrolopyrroles
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays

Definitions

  • the present invention relates to a color liquid crystal display device, a color filter pigment composition for use in the production of a color filter used in a color image pickup tube element, a color composition, and a color filter formed using the same. is there.
  • a liquid crystal layer sandwiched between two polarizing plates controls the amount of light passing through the first polarizing plate by controlling the degree of polarization of light passing through the first polarizing plate.
  • the type using twisted nematic (TN) type liquid crystal is the mainstream.
  • a color filter is a surface of a transparent substrate such as glass, in which two or more kinds of fine band (striped) filter segments of different hues are arranged in parallel or crossing each other, or fine filter segments are arranged vertically and horizontally. It is made up of those arranged in In general, it is often formed from filter segments of three colors of red, green, and blue. Each of these segments is as fine as several microns to several hundreds of microns, and is arranged in a predetermined arrangement for each hue. ing.
  • a transparent electrode for driving liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning liquid crystal in a certain direction is further formed thereon.
  • a high temperature treatment of generally 200 ° C. or higher, preferably 230 ° C. or higher is required in the production process for forming the color filter.
  • a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is mainly used as a method for producing a color filter.
  • a pigment having excellent light resistance and heat resistance such as a diketopyrrolopyrrole pigment, an anthraquinone pigment, a perylene pigment or a disazo pigment, may be used alone or in combination for the red filter segment. It is common.
  • C.I. I. Pigment Red 254 is a pigment having particularly high brightness, and is therefore used as a color filter.
  • C.I. I. Pigment Red 254 is a pigment having particularly high brightness, and is therefore used as a color filter.
  • the diketopyrrolopyrrole pigments that have been refined have the property of being easy to grow crystals due to their intermolecular hydrogen bonds, crystallization occurs in the heating process when forming the color filter, and foreign matter is generated. Is a problem.
  • the diketopyrrolopyrrole pigment can be obtained by the production method disclosed in Patent Document 1 and Patent Document 2 (hereinafter referred to as “succinic acid ester synthesis method”).
  • succinic acid ester synthesis method Methods for obtaining a mixture of at least two structurally different diketopyrrolopyrrole pigments using a plurality of nitrile compounds as raw materials in the succinate synthesis method are disclosed in Patent Document 1, Patent Document 2, and Patent Document 3 Has been.
  • Patent Document 1 and Patent Document 2 hereinafter referred to as “succinic acid ester synthesis method”.
  • Patent Document 4 a mixture of at least two structurally different diketopyrrolopyrrole pigments obtained by a succinate synthesis method using a nitrile compound having a plurality of specific structural formulas as a raw material is used for a color filter.
  • a succinate synthesis method using a nitrile compound having a plurality of specific structural formulas as a raw material is used for a color filter.
  • Patent Documents 5 and 6 a diketopyrrolopyrrole pigment (mainly CI Pigment Red 254) and a diketopyrrolopyrrole compound having at least one specific structural formula are used in combination with a high contrast ratio. There has been proposed and disclosed a coloring composition for a color filter which is present and suppresses crystal precipitation due to a heating process. Patent Document 7 also describes a pigment dispersion composition for a color filter using a diketopyrrolopyrrole pigment.
  • JP 58-210084 A Japanese Patent Application Laid-Open No. 07-90189 JP-A-61-120861 Special table 2007-514798 gazette WO2009 / 081930 pamphlet JP 2009-149707 A WO2009 / 144115 pamphlet
  • the present invention provides a pigment composition for a color filter, a coloring composition, and a color filter using the same, which have a high brightness and a high contrast ratio and do not cause crystal precipitation of a diketopyrrolopyrrole pigment even in a heating process.
  • the task is to do.
  • the present inventors have described C.I. I. As a result of studying various combinations of CI Pigment Red 254 and other diketopyrrolopyrrole pigments, a specific diketopyrrolopyrrole pigment having a pigment structure in which a substituent is introduced asymmetrically is obtained. I. The present inventors have found that a pigment composition contained in a specific ratio with respect to CI Pigment Red 254 is very excellent in achieving the above-described problems, and have reached the present invention.
  • the present invention relates to C.I. I. Pigment Red 254 and a diketopyrrolopyrrole pigment represented by the following formula (1), C.I. I.
  • the present invention relates to a diketopyrrolopyrrole pigment composition for color filters, wherein the mass ratio of Pigment Red 254 to the diketopyrrolopyrrole pigment represented by the following formula (1) is 97: 3 to 85:15.
  • a and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a cyano group, —CF 3 , or —CON (R 1 ) R 2 , and at least one of A and B is —CON (R 1 ) R 2.
  • R 1 and R 2 are each independently hydrogen An atom, an alkyl group having 1 to 20 carbon atoms, or an optionally substituted phenyl group.
  • Another aspect of the present invention is a color composition containing a colorant, a binder resin, and an organic solvent, wherein the colorant contains the diketopyrrolopyrrole pigment composition.
  • Still another aspect of the invention relates to a color filter comprising a filter segment formed from the color filter coloring composition.
  • a pigment composition for a color filter, a colored composition, and a color filter using the same which have high brightness and high contrast ratio and do not cause crystal precipitation of a diketopyrrolopyrrole pigment even in a heating process. Can be provided.
  • C. I. Pigment Red 254 is 3,6-bis (4-chlorophenyl) -2,5-dihydropyrrolo [3,4-c] pyrrole-1,4-dione.
  • Diketopyrrolopyrrole Pigment Composition The diketopyrrolopyrrole pigment composition for color filters according to the present invention (hereinafter, “diketopyrrolopyrrole” may be abbreviated as “DPP”) is C.I. I. Pigment Red 254 and a DPP pigment represented by the following formula (1) (hereinafter, referred to as “specific heterodiketopyrrolopyrrole pigment” and sometimes abbreviated as “specific hetero DPP pigment”) are 97 in mass ratio. : 3 to 85:15.
  • specific hetero DPP pigment a plurality of types may be used in combination.
  • a and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a cyano group, —CF 3 , or —CON (R 1 ) R 2 , and at least one of A and B is —CON (R 1 ) R 2.
  • R 1 and R 2 are each independently hydrogen An atom, an alkyl group having 1 to 20 carbon atoms, or an optionally substituted phenyl group.
  • the alkyl group having 1 to 4 carbon atoms may be linear or branched, and specifically includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Examples thereof include isobutyl group, sec-butyl group, and tert-butyl group.
  • the alkoxyl group having 1 to 4 carbon atoms may be linear or branched, and specifically includes a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert- A butoxy group is mentioned.
  • the alkyl group having 1 to 20 carbon atoms may be linear or branched. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec -Butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, hexadecyl, octadecyl, icosyl, 1,5-dimethylhexyl, 1,6-dimethylheptyl Group, 2-ethylhexyl group and the like, but are not limited thereto.
  • Examples of the phenyl group which may have a substituent include a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a cyano group, a trifluoromethyl group, a nitro group, a carbamoyl group, and a sulfamoyl group. And a phenyl group having one or more substituents.
  • the phenyl group may have two or more different types of substituents.
  • the specific hetero DPP pigment includes at least one of a DPP pigment represented by the following formula (1-1) and a DPP pigment represented by the following formula (1-2).
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an optionally substituted phenyl. Group.
  • the ratio of Pigment Red 254 to the specific hetero DPP pigment is characterized by being in the range of 97: 3 to 85:15 by mass ratio.
  • the ratio of the specific hetero DPP pigment exceeds 15% by mass, an effect of suppressing crystallization is obtained.
  • the excellent color tone of CI Pigment Red 254 is impaired. This is because the specific hetero DPP pigment is C.I. I. This is because the color tone is inferior to that of Pigment Red 254.
  • the ratio of the specific hetero DPP pigment is less than 3% by mass, the effect of increasing the contrast ratio and suppressing the crystal precipitation is not sufficient.
  • I. Pigment Red 254 can be produced by a succinic diester synthesis method. That is, using 2 mol of 4-chlorobenzonitrile per 1 mol of succinic acid diester, in an inert organic solvent such as tert-amyl alcohol, in the presence of an alkali metal or an alkali metal alkoxide, a high temperature of 80 to 110 ° C. By carrying out a condensation reaction in order to produce an alkali metal salt of the DPP compound, and subsequently protonating the alkali metal salt of the DPP compound with water, alcohol, acid, or the like. I. Pigment Red 254 can be obtained.
  • the size of the primary particle diameter obtained can be controlled by the temperature in protonation, the type, ratio and amount of water, alcohol or acid.
  • C. I. The manufacturing method of the pigment red 254 is not limited to this method. Commercially available C.I. I. Pigment Red 254 may be used.
  • C. I. Pigment Red 254 and the specific hetero DPP pigment can be simultaneously produced as a fine particle pigment composition. This can be achieved by using a method using at least two structurally different benzonitrile compounds (hereinafter referred to as “succinic acid diester co-synthesis method”) in the succinic acid diester synthesis method. Specifically, in the method described in Patent Document 5, a plurality of benzonitrile compounds to be used are selected from 4-chlorobenzonitrile and a benzonitrile compound represented by the following formula (2). .
  • a DPP pigment composition containing CI Pigment Red 254 and a specific hetero DPP pigment can be produced.
  • a and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a cyano group, —CF 3 , or —CON (R 1 ) R 2 , and at least one of A and B is —CON (R 1 ) R 2.
  • R 1 and R 2 are each independently hydrogen An atom, an alkyl group having 1 to 20 carbon atoms, or an optionally substituted phenyl group.
  • C. I. Pigment Red 254 and the specific hetero-DPP pigment may be produced separately, but it is desirable to produce a pigment composition by simultaneously synthesizing both by the succinic acid diester co-synthesis method for ease of production. .
  • Succinic acid diester co-synthesis method C.I. I.
  • C.I. I When producing a pigment composition containing CI Pigment Red 254 and a specific hetero DPP pigment, 2 mol of a mixture of 4-chlorobenzonitrile and a benzonitrile compound of the formula (2) is reacted with 1 mol of succinic acid diester. Let At this time, the C.I. I. It is necessary to adjust the mixing ratio (molar ratio) of 4-chlorobenzonitrile and the benzonitrile compound of formula (2) so that the mass ratio of Pigment Red 254 and the specific hetero-DPP pigment is 97: 3 to 85:15. There is.
  • the mixing ratio (molar ratio) between 4-chlorobenzonitrile and the benzonitrile compound of formula (2) varies.
  • the mixing ratio (molar ratio) of 4-chlorobenzonitrile and the benzonitrile compound of the formula (2) is about 80:20 to 98: 2. Become a range.
  • a DPP pigment that is, a diketopyrrolopyrrole pigment containing no p-chlorophenyl group
  • 2 moles of the benzonitrile compound of the formula (2) is reacted with 1 mole of the succinic acid diester
  • the mixing ratio in this range is very small, so there is almost no adverse effect.
  • the reaction ratio of the succinic acid diester to the benzonitrile compound is basically 2 mol of the benzonitrile compound with respect to 1 mol of the succinic acid diester. Using an excess of about 25 mol% of the required molar amount relative to the nitrile compound is effective for improving the yield.
  • the mass ratio between Pigment Red 254 and the specific hetero DPP pigment can be determined by analysis using TOF-MASS, FD-MASS, LC-MASS, or NMR.
  • a DPP pigment composition is obtained by stirring at room temperature with di-tert-butyl dicarbonate and 4-dimethylaminopyridine in tetrahydrofuran. It may be determined by analysis using NMR, MASS, LC-MASS or the like after conversion to the DPP compound.
  • the hydrogen of the NH group of the pyrrolopyrrole ring may be substituted with an alkyl group using an alkyl halide or the like and converted into soluble DPP, and then determined by the above analysis.
  • the DPP pigment composition a pigment derivative can be used for the purpose of suppressing pigment crystal growth and improving pigment dispersibility. That is, in one embodiment, the DPP pigment composition further contains a dye derivative.
  • the dye derivative used include quinacridone derivatives, diketopyrrolopyrrole derivatives, benzoisoindole derivatives, anthraquinone derivatives, dianthraquinone derivatives, thiazine indigo derivatives, azo dye derivatives, and quinophthalone derivatives. Multiple types of dye derivatives may be used.
  • the structure of the pigment derivative can be represented by the following formula (3), but the pigment derivative is not limited to those represented by these formulas.
  • P is quinacridone residue, diketopyrrolopyrrole residue, benzoisoindole residue, anthraquinone residue, dianthraquinone residue, thiazineindigo residue, azo dye residue, or quinophthalone residue
  • m is an integer of 1 to 4
  • Each L is independently —OH; —SO 3 H, —COOH, a monovalent to trivalent metal salt of these acidic groups, an alkylammonium salt; a phthalimidomethyl group which may have a substituent; or It is a group represented by any of the following formulas (a), (b), (c), (d), (e), and (f).
  • X is, -SO 2 -, - CO - , - CH 2 -, - CH 2 NHCOCH 2 -, - CH 2 NHSO 2 CH 2 -, or a direct bond
  • Y is —NH—, —O—, —S—, or a direct bond
  • n is an integer of 1 to 10
  • R 3 and R 4 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 30 carbon atoms, an optionally substituted alkenyl group having 2 to 30 carbon atoms, or R 3 and R 4 together are a heterocyclic ring which may have a substituent, further containing a nitrogen, oxygen or sulfur atom
  • R 5 , R 6 , R 7 , R 8 and R 9 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an optionally substituted carbon.
  • R 10 is a substituent represented by the formula (a) or the formula (b)
  • R 11 is a chlorine atom, —OH, an alkoxyl group, a substituent represented by the formula (a) or the formula (b)
  • Z is —CONH—, —NHCO—, —SO 2 NH—, or —NHSO 2 —
  • R 12 is a hydrogen atom, —NH 2 , —NHCOCH 3 , —NHR 13 , or a substituent represented by the formula (c), wherein R 13 has 1 to carbon atoms that may have a substituent.
  • Examples of the monovalent to trivalent metal in L in the above formula (3) include sodium, potassium, magnesium, calcium, iron, and aluminum.
  • Alkyl ammonium salts include ammonium salts of long-chain monoalkylamines such as octylamine, laurylamine, or stearylamine, or quaternary compounds such as palmityltrimethylammonium salt, dilauryldimethylammonium salt, or distearyldimethylammonium salt. Examples include alkylammonium salts.
  • the alkyl group which may have a substituent As the phthalimidomethyl group which may have a substituent, the alkyl group which may have a substituent, the alkenyl group which may have a substituent, or the heterocyclic substituent which may have a substituent, A halogen atom, a cyano group, a nitro group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, an N-substituted sulfamoyl group, an alkoxyl group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, and the like. However, it is not limited to these.
  • the alkyl group and alkenyl group may be linear or branched.
  • the dye derivative is a sulfonation reaction by heating in sulfuric acid or fuming sulfuric acid, a phthalimide methylation reaction in which dehydration condensation is performed with N-hydroxymethylphthalimide in sulfuric acid, and chlorosulfonated using chlorosulfonic acid and thionyl chloride. It is synthesized by a known production method such as sulfonamidation reaction in which an amine component such as dimethylaminopropylamine is reacted.
  • Examples of the amine component used for forming the substituent represented by the above formula (a), formula (b), and formula (c) include dimethylamine, diethylamine, methylethylamine, N, N-ethyl. Isopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N , N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, dicyclohexylamine, di (2-ethylhexyl) ) Amine, dioctylamine, N,
  • the azo dye derivative can also be produced by introducing the substituent into a diazo component or a coupling component in advance and then performing a coupling reaction.
  • the method of using the pigment derivative is to use the DPP pigment composition in a pigment carrier (also referred to as a pigment composition carrier), that is, in a binder resin (in the case of using a resin type dispersant, in a binder resin and a resin type dispersant).
  • a pigment carrier also referred to as a pigment composition carrier
  • a binder resin in the case of using a resin type dispersant, in a binder resin and a resin type dispersant.
  • a method of mixing in water or an organic solvent at the time of pigment production, or a method of adding at the time of salt milling can be mentioned.
  • the method of mixing the pigment derivative in water or an organic solvent at the time of pigment production or the method of adding it at the time of salt milling exhibits the effect of suppressing the crystal growth of the DPP pigment, but exhibits the effect of suppressing the crystal growth.
  • the dye derivative is efficiently adsorbed on the surface of the DPP pigment and does not easily desorb. For this reason, a dye derivative partially having a chemical structure similar to that of the pigment to be used is often selected. For these reasons, dye derivatives having a quinacridone structure, a DPP structure, a thiazine indigo structure, or a benzoisoindole structure are generally effective for DPP pigments.
  • a dye derivative when used, it is required that the color tone of the DPP pigment composition is not impaired as much as possible. From the viewpoint of hue, it is preferable to use a DPP derivative, benzoisoindole derivative, thiazineindigo derivative, azo dye derivative, or quinophthalone derivative that exhibits a yellow or orange color.
  • the compounding amount of the dye derivative is preferably 0.5 parts by mass or more, more preferably 3 parts by mass or more with respect to 100 parts by mass of the pigment in order to sufficiently exhibit the crystal growth inhibiting effect. .
  • the amount of the dye derivative is preferably 40 parts by mass or less and more preferably 35 parts by mass or less with respect to 100 parts by mass of the pigment. That is, the blending amount of the dye derivative is preferably in the range of 0.5 to 40% by mass with respect to 100% by mass of the pigment, and more preferably in the range of 3 to 35% by mass with respect to 100% by mass of the pigment. is there.
  • DPP derivative As the DPP derivative, specifically, a compound represented by the following formula (5) or formula (6) can be used, but is not limited thereto.
  • benzoisoindole derivatives As the benzoisoindole derivative, specifically, a compound represented by the following formula (7) can be used, but is not limited thereto.
  • anthraquinone derivative Specifically as an anthraquinone derivative, the compound represented by following formula (8) can be used, However, It is not limited to these.
  • dianthraquinone derivatives specifically, a compound represented by the following formula (9) can be used, but is not limited thereto.
  • thiazine indigo derivatives specifically, a compound represented by the following formula (10) can be used, but is not limited thereto.
  • azo dye derivatives specifically, a compound represented by the following formula (11), formula (12), or formula (13) can be used, but is not limited thereto.
  • quinophthalone derivatives specifically, compounds represented by the following formulas (14-1) to (14-13) can be used, but are not limited thereto.
  • the DPP pigment composition according to the present invention preferably has a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution.
  • the average primary particle diameter (that is, the average primary particle diameter of each pigment particle (and dye derivative) constituting the pigment composition) obtained by TEM (transmission electron microscope) of the DPP pigment composition is calculated as follows.
  • the thickness is preferably 5 nm or more, and in order to obtain a sufficient contrast ratio, it is preferably 70 nm or less.
  • the more preferable average primary particle diameter is 10 nm or more and 40 nm or less.
  • the average primary particle diameter is in the above range at the stage when the DPP pigment composition is produced by the above synthesis method, it may be used as it is. Otherwise, the pigment is refined and adjusted by a salt milling process or the like. It is desirable to granulate.
  • a salt milling process is preferable for refining the pigment composition.
  • Salt milling is a process in which a mixture of a pigment composition, a water-soluble inorganic salt, and a water-soluble organic solvent is heated using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill. After mechanically kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water.
  • a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill.
  • the water-soluble inorganic salt works as a crushing aid, and it is thought that the pigment is crushed using the high hardness of the inorganic salt during salt milling, thereby generating an active surface and causing crystal growth. Yes. Therefore, the crushing of the pigment and the crystal growth occur simultaneously during the kneading, and the primary particle diameter of the pigment obtained varies depending on the kneading conditions.
  • the heating temperature is preferably 35 to 150 ° C. in order to promote appropriate and sufficient crystal growth as a color filter colorant.
  • the heating temperature is less than 35 ° C., crystal growth does not occur sufficiently, and the shape of the pigment composition particles may become nearly amorphous.
  • the heating temperature exceeds 150 ° C., crystal growth proceeds.
  • the primary particle size of the pigment composition becomes large, which is not preferable as a colorant for a color filter.
  • the kneading time for the salt milling treatment is preferably 2 to 24 hours from the viewpoint of the balance between the particle size distribution of the primary particles of the salt milling treatment pigment and the cost required for the salt milling treatment.
  • water-soluble inorganic salt used for the salt milling treatment 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 mass, and most preferably 300 to 1200 parts by mass, based on the total amount of pigment (100 parts by mass), from the viewpoint of both processing efficiency and production efficiency.
  • the water-soluble organic solvent is not particularly limited as long as it functions to wet the pigment composition and the water-soluble inorganic salt and 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 100 parts by weight of the pigment composition.
  • a pigment derivative When performing the salt milling treatment, a pigment derivative may be used in combination to improve kneading efficiency, which is very effective for making the pigment composition finer and sized.
  • this pigment derivative the above-mentioned pigment derivatives are preferably used, but are not limited thereto.
  • the amount of the dye derivative used is preferably such that it does not affect the color tone, that is, in the range of 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment composition.
  • a resin when performing the salt milling treatment, 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 is preferably solid at room temperature, 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 mass with respect to 100 parts by mass of the pigment composition.
  • the DPP pigment composition according to the present invention can be used as a colored composition when used in combination with a binder resin and an organic solvent.
  • This coloring composition is particularly preferably used for a color filter. That is, this coloring composition contains a coloring agent, a binder resin, and an organic solvent, and this coloring agent contains the DPP pigment composition according to the present invention.
  • a colorant other than the DPP pigment composition (other colorant) may be used in combination.
  • the other colorant is a pigment or dye other than the above DPP pigment composition, and is used in combination as necessary for the purpose of adjusting the chromaticity within the range not impairing the effects of the present invention. It may be a component. Multiple other colorants may be used.
  • red dyes examples include xanthene series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and anthraquinone series.
  • xanthene series examples include xanthene series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and anthraquinone series.
  • C.I. I. examples thereof include salt-forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338.
  • Preferred examples of the colorant used in combination include C.I. I. Pigment red 177, 242 and C.I. I. Pigment yellow 139, 150, 185.
  • the lightness and contrast ratio are excellent in the total amount of the colorant (total amount of the DPP pigment composition and other colorant) (100% by mass).
  • the DPP pigment composition is preferably in the range of 40% by mass to 100% by mass, more preferably in the range of 60% by mass to 100% by mass, from the viewpoint of sufficiently exhibiting the above effects.
  • binder resin examples of the binder resin contained in the coloring composition include conventionally known thermoplastic resins and thermosetting resins. A plurality of types of binder resins may be used.
  • 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, polyurethane resin Polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.
  • 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 is preferable.
  • an alkali-soluble vinyl resin copolymerized with an acidic group-containing ethylenically unsaturated monomer it is preferable to use an energy ray curable resin having an ethylenically unsaturated active double bond.
  • 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.
  • (meth) acrylic acid refers to both acrylic acid and methacrylic acid, and its derivatives are used in the same meaning.
  • Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, aldehyde groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc.
  • a resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used.
  • a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an ⁇ -olefin-maleic anhydride copolymer is half-treated with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate.
  • An esterified product is also used.
  • thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferred as the color filter coloring composition.
  • the following are mentioned as a monomer which comprises the said thermoplastic resin. Of these, a plurality of types of monomers may be used.
  • 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.
  • an epoxy resin and a melamine resin are used more suitably from a viewpoint of heat resistance improvement.
  • the weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 to 50,000 in order to disperse the colorant preferably.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 40,000, and the value of Mw / Mn is preferably 10 or less.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are obtained by connecting four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation.
  • HCV-8120GPC gel permeation chromatography
  • This is a polystyrene-equivalent molecular weight measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by the company and using tetrahydrofuran as the mobile phase.
  • the coloring composition When the coloring composition is used as a coloring composition for a color filter, in the binder resin, a carboxyl group that acts as a pigment adsorbing group and an alkali-soluble group during development, and an aliphatic group that acts as an affinity group for the pigment carrier and solvent And the balance of aromatic groups is important for pigment dispersibility, developability, and durability.
  • a resin having an acid value of 20 to 300 mgKOH / g it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. If the acid value is less than 20 mgKOH / g, the solubility in the developing solution is poor and fine pattern formation may be difficult, and if it exceeds 300 mgKOH / g, the fine pattern may not remain in development.
  • the amount of the binder resin is preferably 20 parts by mass or more in order to obtain film formability and various resistances based on the total mass of the colorant (that is, with respect to 100 parts by mass of the colorant). In order to ensure the density and color characteristics, the amount is preferably 500 parts by mass or less.
  • the pigment composition is sufficiently dispersed in the pigment composition carrier, and is applied onto a substrate such as a glass substrate so as to have a dry film thickness of 0.2 to 5 ⁇ m to form a filter segment.
  • an organic solvent is included.
  • the organic solvent is selected in consideration of good applicability of the coloring composition, solubility of each component of the coloring composition, and safety.
  • 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.
  • aliphatic hydroxy acid esters such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol
  • glycol acetates such as monomethyl ether acetate and ethylene glycol monoethyl ether acetate
  • aromatic alcohols such as benzyl alcohol
  • alicyclic ketones such as cyclohexanone.
  • the blending amount of the organic solvent is 500, based on the total mass of the colorant as a reference (100 parts by mass) from the viewpoint of adjusting the colored composition to an appropriate viscosity and forming a filter segment having a desired uniform film thickness. It is preferably used in an amount of ⁇ 4000 parts by mass.
  • the coloring composition is C.I. I.
  • a DPP pigment composition containing Pigment Red 254 and a specific hetero DPP pigment in a specific ratio in a colorant carrier comprising the binder resin and an organic solvent, a kneader, a two-roll mill, a three-roll mill, a ball mill, It can be produced by finely dispersing using various dispersing means such as a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor.
  • the DPP pigment composition and other colorants may be simultaneously dispersed in the colorant carrier, or those separately dispersed in the colorant carrier may be mixed.
  • a dispersion aid such as a pigment derivative, a resin-type dispersant, and a surfactant may be appropriately contained. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the color composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has contrast and viscosity stability. Become good.
  • the resin-type dispersant has a pigment-affinity part having the property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize.
  • 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.
  • Oil-soluble dispersants such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc.
  • Resin water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more, not necessarily limited thereto.
  • Anionic surfactants such as triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate;
  • Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol mono
  • the total amount of the colorant is used as a standard (100 parts by mass), and may be blended in an amount of 0.1 part by mass or more in order to obtain the blending effect. It is preferable to use it in an amount of 55 parts by mass or less in order to obtain appropriate dispersibility. That is, it is preferably 0.1 to 55 parts by mass, and more preferably 0.1 to 45 parts by mass.
  • the colored composition of the present invention further contains a photopolymerizable monomer and / or a photopolymerization initiator, and can be used as a photosensitive colored composition.
  • the photosensitive coloring composition is a color filter coloring composition.
  • the photopolymerizable monomer used includes monomers or oligomers that are cured by ultraviolet rays or heat to produce a transparent resin, and these can be used alone or in combination of two or more.
  • the amount of the monomer is preferably 5 to 400 parts by mass based on the total weight of the colorant (100 parts by mass), and more preferably 10 to 300 parts by mass from the viewpoint of photocurability and developability. preferable.
  • Examples of monomers and oligomers that are cured by ultraviolet rays or heat to produce a transparent resin include: 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 diglycidyl ether di (meth)
  • Photopolymerization initiator When a photosensitive coloring composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, it can be adjusted in the form of a solvent development type or alkali development type colored resist material by adding a photopolymerization initiator. .
  • photopolymerization initiators can be used alone or as a mixture of two or more at any ratio as required.
  • These photopolymerization initiators are preferably 2 to 200 parts by mass based on the total amount of the colorant in the photosensitive coloring composition (100 parts by mass), and 3 to 3 in terms of photocurability and developability. More preferably, it is 150 parts by mass.
  • the photosensitive coloring composition can further 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, tetraphenyl
  • Two or more sensitizers may be used at an arbitrary ratio as necessary.
  • the blending amount when using the sensitizer is preferably 3 to 60 parts by mass based on the total weight (100 parts by mass) of the photopolymerization initiator contained in the photosensitive coloring composition. From the viewpoints of colorability and developability, it is more preferably 5 to 50 parts by mass.
  • the coloring composition or the photosensitive coloring composition can contain an amine compound that functions to reduce dissolved oxygen.
  • a plurality of types of amine compounds may be used in combination.
  • 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.
  • 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 coloring composition or the photosensitive coloring composition.
  • a 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 BYK Chemie.
  • dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie.
  • the leveling agent is preferably used in an amount of 0.003 to 0.5% by mass in the total weight (100% by mass) of the colored composition or the photosensitive colored composition.
  • a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, having a hydrophilic group but low solubility in water, and when added to a coloring composition, It has the feature of low surface tension lowering ability, and also has good wettability to the glass plate even though the surface tension lowering ability is low.
  • those capable of suppressing the chargeability can be preferably used.
  • dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used.
  • the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
  • the bonding form of polyalkylene oxide units with dimethylpolysiloxane is as follows: pendant type in which polyalkylene oxide units are bonded in repeating units of dimethylpolysiloxane, terminal-modified type in which the end of dimethylpolysiloxane is bonded, and alternating with dimethylpolysiloxane. Any of a linear block copolymer type bonded repeatedly 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.
  • An anionic, cationic, nonionic or amphoteric surfactant can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
  • 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.
  • Examples of the chaotic surfactant that is supplementarily added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts.
  • 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 ether type or ester type surfactants such as polyethylene glycol monolaurate.
  • amphoteric surfactants such as alkylbetaines such as alkyldimethylaminoacetic acid betaine and alkylimidazolines may be used, and fluorine or silicone surfactants may be used.
  • the coloring composition or the photosensitive coloring composition may contain a curing agent and / or a curing accelerator as necessary in order to assist the curing of the thermosetting resin.
  • a 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. These may be used alone or in combination of two or more.
  • the curing agent is preferably contained in an amount of 1 to 100 parts by mass with respect to the total amount (100 parts by mass) of the thermosetting resin.
  • 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 coloring composition or the photosensitive coloring composition may contain a storage stabilizer in order to stabilize the viscosity with time.
  • 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.
  • the storage stabilizer can be used in an amount of 0.1 to 10 parts by mass based on the total amount of the colorant (based on 100 parts by mass of the colorant).
  • Vinylsilanes such as vinyltris ( ⁇ -methoxyethoxy) silane, vinylethoxysilane, vinyltrimethoxysilane; (meth) acrylsilanes such as ⁇ -methacryloxypropyltrimethoxysilane; ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) methyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, ⁇ - (3, Epoxy silanes such as 4-epoxycyclohexyl) methyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane; N- ⁇ (aminoethyl) ⁇ -aminopropyl
  • the coloring composition and the photosensitive coloring composition coarse particles having a primary particle size of 5 ⁇ m or more, preferably 1 ⁇ m or more, more preferably 0, by means of centrifugation, filtration with a sintered filter or a membrane filter, or the like. It is preferable to remove coarse particles of 5 ⁇ m or more and mixed dust.
  • the coloring composition does not substantially contain particles of 0.5 ⁇ m or more, and more preferably does not contain particles larger than 0.3 ⁇ m (0.3 ⁇ m or less).
  • Color filter which concerns on this invention has a filter segment formed from the coloring composition containing the DPP type pigment composition which concerns on this invention, or a photosensitive coloring composition. That is, the color filter according to the present invention includes a red filter segment, a green filter segment, and a blue filter segment, and the red filter segment contains a DPP pigment composition according to the present invention or a photosensitive coloring. It is formed from a composition.
  • the green filter segment can be formed using an ordinary green coloring composition containing an arbitrary green pigment and an optional colorant carrier (binder resin and organic solvent, the same applies hereinafter).
  • an optional colorant carrier binder resin and organic solvent, the same applies hereinafter.
  • the green pigment include C.I. I. Pigment Green 7, 10, 36, 37, 58, etc. are used.
  • a yellow pigment can be used in combination with the green coloring composition.
  • yellow pigments that can be used in combination include 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, 172, 173, 174, 175, 176, 177, 179, 180, 181,
  • the blue filter segment can be formed using a normal blue coloring composition containing an arbitrary blue pigment and an arbitrary colorant carrier.
  • blue pigments include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. are used.
  • a purple pigment can be used in combination with the blue coloring composition.
  • purple pigments that can be used in combination include C.I. I. And violet pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50.
  • a basic dye exhibiting blue or purple or a salt-forming compound of an acid dye can also be used.
  • a xanthene dye is preferable in terms of heat resistance and lightness.
  • the color filter can be manufactured by a printing method or a photolithography method.
  • the formation of the filter segment by the printing method can be patterned simply by repeating the printing and drying of the coloring composition prepared as the printing ink. Therefore, the color filter manufacturing method is low in cost and excellent in mass productivity. 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 is not dried and solidified on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.
  • 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 with a spray or the like to remove uncured parts to form a desired pattern, the same operation is repeated for other colors to produce a color filter. can do. 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, and the colored composition or the photosensitive colored composition according to the present invention can be used in any method.
  • the electrodeposition method is a method for producing a color filter by electrodepositing each color filter segment on a transparent conductive film by electrophoresis of colloidal particles using a transparent conductive film formed on a substrate.
  • 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 as necessary.
  • part means “part by mass”.
  • a DPP derivative of the formula (6-3) a benzoisoindole derivative of the formula (7-1), an anthraquinone derivative of the formula (8-5), and a formula ( The quinophthalone derivative of 14-1) was used.
  • the average primary particle diameter of the produced pigment composition was measured (calculated) by the following method. Propylene glycol monomethyl ether acetate was added to the powder of the pigment composition, a small amount of Disperbyk-161 was added as a resin-type dispersant, and the sample for measurement was prepared by treatment with ultrasonic waves for 1 minute. This sample was taken with a transmission (TEM) electron microscope and three photographs (for 3 fields of view) showing the primary particles of 100 or more pigments were taken, and the size of 100 primary particles was measured in order from the upper left. did.
  • TEM transmission
  • the short axis diameter and the long axis diameter of the primary particles of each pigment are measured in nm units, the average is the primary particle diameter of the pigment particles, and a total of 300 distributions are created in increments of 5 nm.
  • a median value in increments of 5 nm was approximated as the particle diameter of those particles, and the number average particle diameter was calculated by calculating based on each particle diameter and the number thereof.
  • the identification of the specific hetero-DPP pigment is performed by using the MALDI mass spectrometer autoflex II (hereinafter referred to as TOF-MS) manufactured by Bruker Daltonics, Inc., with the coincidence between the molecular ion peak of the obtained mass spectrum and the mass number obtained by calculation. Identified.
  • TOF-MS MALDI mass spectrometer autoflex II
  • the m / Z value was 365.09, and it was identified as a specific hetero DPP pigment represented by the formula (1-1a).
  • the following specific hetero DPP compounds were similarly identified for the synthesized products.
  • reaction vessel 1 Into the reaction vessel 1, 66.0 parts of tert-amyl alcohol was added and 10 parts of 60% NaH was added while cooling in a water bath, and the mixture was heated and stirred at 90 ° C. Next, 60 parts of tert-amyl alcohol, 27.9 parts of the compound of the above formula (15), and 45.7 parts of 4- (octadecylcarbamoyl) benzonitrile are placed in the reaction vessel 2 and dissolved by heating. Over 2 hours. After reacting at 120 ° C.
  • Pigment Composition 1 (R-1) was obtained.
  • the average primary particle size was 29.5 nm.
  • Pigment composition 2 was prepared in the same manner as in the production of pigment composition 1 (R-1) except that the specific hetero DPP pigment of formula (1-1a) was changed to the specific hetero DPP pigment of formula (1-1b). (R-2) 96.4 parts were obtained. The average primary particle size was 27.5 nm.
  • Example 3> (Production of Pigment Composition 3 (R-3)) C. I. Except that the mixing ratio of Pigment Red 254 and the specific hetero-DPP pigment of the formula (1-1c) was changed to 97/3 (mass ratio), it was carried out in the same manner as in the production of pigment composition 1 (R-1). 97.2 parts of pigment composition 3 (R-3) was obtained. The average primary particle size was 30.2 nm.
  • Pigment composition 4 was prepared in the same manner as in the production of pigment composition 1 (R-1), except that the specific hetero DPP pigment of formula (1-1a) was changed to the specific hetero DPP pigment of formula (1-1c). 95.8 parts of (R-4) was obtained. The average primary particle size was 26.9 nm.
  • Example 5 (Production of Pigment Composition 5 (R-5)) C.
  • Pigment Red 254 and the specific hetero DPP pigment of formula (1-1c) were used in the same manner as in the preparation of Pigment Composition 1 (R-1) except that 100 parts of a 90/10 (mass ratio) mixture was used. 95.2 parts of composition 5 (R-5) was obtained. The average primary particle size was 25.2 nm.
  • Example 6> (Production of Pigment Composition 6 (R-6)) C.
  • Pigment Red 254 and the specific hetero DPP pigment of formula (1-1c) were used in the same manner as in the production of Pigment Composition 1 (R-1) except that 100 parts of a 85/15 (mass ratio) mixture was used. 96.2 parts of composition 6 (R-6) were obtained.
  • the average primary particle size was 27.7 nm.
  • Pigment composition 7 was prepared in the same manner as in the production of pigment composition 1 (R-1) except that the specific hetero DPP pigment of formula (1-1a) was changed to the specific hetero DPP pigment of formula (1-1d). 97.8 parts of (R-7) was obtained. The average primary particle size was 25.9 nm.
  • Example 8> (Production of Pigment Composition 8 (R-8)) Except that the specific hetero DPP pigment of the formula (1-1c) was changed to the specific hetero DPP pigment of the formula (1-1d), the same procedure as in the production of the pigment composition 6 (R-6) was carried out, and a pigment composition 8 95.7 parts of (R-8) was obtained.
  • the average primary particle size was 28.9 nm.
  • Pigment composition 9 was carried out in the same manner as in the production of pigment composition 1 (R-1) except that the specific hetero DPP pigment of formula (1-1a) was changed to the specific hetero DPP pigment of formula (1-1g). 96.4 parts of (R-9) was obtained. The average primary particle size was 32.5 nm.
  • Pigment composition 10 was prepared in the same manner as in the production of pigment composition 1 (R-1) except that the specific hetero DPP pigment of formula (1-1a) was changed to the specific hetero DPP pigment of formula (1-1h). 97.2 parts of (R-10) were obtained. The average primary particle size was 28.5 nm.
  • Pigment composition 11 was prepared in the same manner as in the production of pigment composition 6 (R-6) except that the specific hetero DPP pigment of formula (1-1c) was changed to the specific hetero DPP pigment of formula (1-1h). 96.5 parts of (R-11) was obtained. The average primary particle size was 26.9 nm.
  • Example 12 (Production of Pigment Composition 12 (R-12)) Except that the specific hetero DPP pigment of the formula (1-1a) was changed to the specific hetero DPP pigment of the formula (1-2c), the same procedure as in the production of the pigment composition 1 (R-1) was carried out. 95.9 parts of (R-12) was obtained. The average primary particle size was 31.2 nm.
  • Example 13> (Production of Pigment Composition 13 (R-13)) Except that the specific hetero DPP pigment of the formula (1-1a) was changed to the specific hetero DPP pigment of the formula (1-2d), the same procedure as in the production of the pigment composition 1 (R-1) was carried out, and the pigment composition 13 96.6 parts of (R-13) was obtained.
  • the average primary particle size was 32.7 nm.
  • Example 14> (Production of Pigment Composition 14 (R-14)) Except that the specific hetero DPP pigment of the formula (1-1a) was changed to the specific hetero DPP pigment of the formula (1-2e), the same procedure as in the production of the pigment composition 1 (R-1) was carried out. 97.3 parts of (R-14) was obtained. The average primary particle size was 30.9 nm.
  • Example 15> (Production of Pigment Composition 15 (R-15)) C.
  • 100 parts of a 95/5 (mass ratio) mixture of CI Pigment Red 254 and a specific hetero DPP pigment of formula (1-1c), 3.0 parts of a pigment derivative of a benzoisoindole derivative of formula (7-1), sodium chloride 1000 parts and 120 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is poured into warm water, stirred for 1 hour while heating to about 80 ° C.
  • pigment composition 15 (R-15) was obtained.
  • the average primary particle size was 24.1 nm.
  • Example 16> (Production of Pigment Composition 16 (R-16)) To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. Meanwhile, 88 parts of diisopropyl succinate, 110.1 parts of 4-chlorobenzonitrile and 11.2 parts of the benzonitrile compound of the formula (2-1c) are added to a glass flask and heated to 90 ° C. with stirring. Dissolved to prepare solutions of these mixtures.
  • the heated solution of the mixture was slowly dropped into the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropwise addition, heating and stirring were continued at 90 ° C. for 2 hours to obtain an alkali metal salt of a DPP compound. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were added to a glass jacketed reaction vessel, and cooled to ⁇ 10 ° C. While rotating the shear disk having a diameter of 8 cm at 4000 rpm using a high-speed stirring disperser, the cooled mixture was cooled to 75 ° C., and the previously obtained alkali metal salt solution of the DPP compound was Small portions were added.
  • the rate of addition of the alkali metal salt of the DPP compound at 75 ° C. is adjusted while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. While being added in small portions over approximately 120 minutes.
  • red crystals were precipitated to form a red suspension.
  • the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C. to make a suspension with a methanol concentration of about 90%, and stirred at 5 ° C.
  • pigment composition 16 (R-16) were obtained in the same manner as in the production of pigment composition 1 (R-1) except that 100.0 parts of the obtained DPP pigment composition was used. It was.
  • the average primary particle size was 26.5 nm.
  • Pigment composition 17 (R-17) 97.3 parts were obtained in the same manner as in the production of pigment composition 1 (R-1) except that 100.0 parts of Pigment Red 254 was used alone.
  • the average primary particle size was 33.9 nm.
  • Pigment composition 19 (R-19) C.
  • Pigment composition was prepared in the same manner as in Pigment Composition 1 (R-1) except that 100 parts of a 30/70 (mass ratio) mixture of CI Pigment Red 254 and the specific hetero DPP pigment of formula (1-1c) was used. 95.8 parts of product 19 (R-19) were obtained. The average primary particle size was 38.8 nm.
  • DPP pigment compositions 1 to 23 are shown in Table 1. “PR254” described in Table 1 is C.I. I. Pigment Red 254 is meant.
  • Manufacture of other pigments (Manufacture of dianthraquinone pigment 1 (PR177-1)) 90 parts of a dianthraquinone pigment (CI Pigment Red 177), 900 parts of sodium chloride and 110 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is poured into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. overnight for grinding. As a result, 85.0 parts of anthraquinone pigment 1 (PR177-1) were obtained. The average primary particle size was 38.2 nm.
  • an acrylic resin solution 2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • the weight average molecular weight of the acrylic resin is a polystyrene equivalent weight average molecular weight measured by GPC (gel permeation chromatography).
  • Example 33> (Preparation of colored composition 17 (RP-17)) A colored composition 17 (RP-17) was produced in the same manner as the colored composition 1 (RP-1) except that a mixture having the following composition was used.
  • DPP pigment composition 4 (R-4) 11.0 parts DPP dye derivative of formula (6-3) 1.0 part Resin-type dispersant (BYK161, 30% solution manufactured by BYK Chemie) 6.0 parts Acrylic Resin solution 1 31.0 parts Propylene glycol monomethyl ether acetate 51.0 parts
  • a coloring composition 25 (RP-25) for toning was prepared in the same manner as the coloring composition 1 (RP-1) except that the mixture having the following composition was used.
  • Dianthraquinone pigment (PR177-1) 10.8 parts
  • Anthraquinone dye derivative of formula (8-5) 1.2 parts
  • Acrylic resin solution 1 40.0 parts
  • Propylene glycol monomethyl ether acetate 48.0 parts
  • Coloring composition 1 (RP-1) 38.1 parts Coloring composition 25 (RP-25) 3.9 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (“Irgacure 907” manufactured by Ciba Japan) 2.0 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 part Ethylene glycol monomethyl ether acetate 39. 6 copies
  • Coloring composition 1 was changed to coloring compositions 2 to 17 (RP-2 to 17), and further, coloring compositions 2 to 17 (RP-2 to 17) and coloring composition 25 (RP-25) ) was changed in the same manner as in Example 34 except that the ratio was changed within 42 parts of the total amount of the colored composition.
  • Photosensitive colored compositions 2 to 17 (RP-2 to 17) were produced.
  • the ratio of composition 25 (RP-25) was changed.
  • the light emitted from the backlight unit for liquid crystal display is polarized through the polarizing plate, passes through the dried coating film of the colored composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate.
  • the polarized light is polarized when the polarizing plate is parallel.
  • the amount of light transmitted through the plate is reduced and the polarizing plate is perpendicular, a part of the light is transmitted through the polarizing plate. This transmitted light was measured as the luminance on the polarizing plate, and the ratio (contrast ratio) between the luminance when the polarizing plate was parallel and the luminance when it was orthogonal was calculated.
  • Example 34 In the comparison of Example 34, Example 35, Example 37, Example 40, Example 42, and Example 43, it has a substituent that can be expected to have a steric hindrance effect such as an alkyl group having 4 or more carbon atoms or a phenyl group. This was found to be more effective in increasing the contrast ratio and suppressing crystal precipitation.
  • Example 37 In the comparison between Example 37 and Example 49, a pigment composition produced by a succinic acid diester co-synthesis method and C.I. I. It was found that the same effect was obtained with a pigment composition prepared by separately synthesizing Pigment Red 254 and a specific hetero DPP pigment and mixing them during the salt milling treatment.
  • Green coloring composition 1 (GP-1)
  • the mixture having the composition shown below was uniformly stirred and mixed, dispersed with picomil for 8 hours using zirconia beads having a diameter of 0.1 mm, filtered through a 5 ⁇ m filter, and green colored composition 1 (GP-1) was made.
  • Green pigment (CI Pigment Green 36) 6.8 parts
  • Yellow pigment (CI Pigment Yellow 150) 5.2 parts
  • Resin type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 part Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • Green coloring composition 1 (GP-1) 42.0 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907" manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 39.6 parts ethylene glycol monomethyl ether acetate
  • Blue coloring composition 1 (BP-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • 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.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)

Abstract

L'invention porte sur une composition de pigment dicétopyrrolopyrrole pour un filtre coloré, comprenant du pigment rouge C. I. 254 et un pigment dicétopyrrolopyrrole représenté par la formule (1) en un rapport de 97:3-85:15 en masse. (Dans la formule (1), A et B représentent chacun indépendamment un atome d'hydrogène ou un substituant, A et/ou B représentant -CON(R1)R2 ; et R1 et R2 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle ayant 1-20 atomes de carbone ou un groupe phényle qui peut avoir un substituant.)
PCT/JP2012/054573 2011-03-02 2012-02-24 Composition de pigment pour filtre coloré, composition colorée et filtre coloré WO2012117965A1 (fr)

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JP2011-044576 2011-03-02
JP2011044576A JP2012181378A (ja) 2011-03-02 2011-03-02 カラーフィルタ用顔料組成物、着色組成物、およびカラーフィルタ

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WO2020075569A1 (fr) * 2018-10-11 2020-04-16 富士フイルム株式会社 Composition de coloration, film, filtre coloré ainsi que procédé de fabrication de celui-ci, structure, élément d'imagerie à l'état solide, et dispositif d'affichage d'image
WO2020241535A1 (fr) 2019-05-31 2020-12-03 富士フイルム株式会社 Capteur optique et dispositif de détection
WO2021039253A1 (fr) 2019-08-30 2021-03-04 富士フイルム株式会社 Composition, film, filtre optique et procédé de production associé, élément d'imagerie à semi-conducteurs, capteur infrarouge et module de capteur
WO2021039205A1 (fr) 2019-08-29 2021-03-04 富士フイルム株式会社 Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges

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JP6194671B2 (ja) * 2013-06-12 2017-09-13 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
WO2017038252A1 (fr) * 2015-09-04 2017-03-09 富士フイルム株式会社 Matériau, composition, composition durcissable, film durci, filtre optique, élément d'imagerie solide, capteur de rayon infrarouge, module de caméra et procédé de production dudit matériau
JP6919234B2 (ja) * 2017-03-07 2021-08-18 東洋インキＳｃホールディングス株式会社 ジケトピロロピロール顔料組成物、該顔料組成物を用いたカラーフィルタ用組成物およびカラーフィルタ
KR102174436B1 (ko) * 2017-08-17 2020-11-04 주식회사 엘지화학 불용성 안료 화합물의 정성분석방법
JP7077765B2 (ja) * 2018-05-17 2022-05-31 東洋インキＳｃホールディングス株式会社 カラーフィルタ用赤色着色組成物およびカラーフィルタの製造方法

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JP2000089025A (ja) * 1998-09-14 2000-03-31 Fuji Photo Film Co Ltd カラーフィルター用感光性着色組成物
JP2003177231A (ja) * 2001-12-11 2003-06-27 Dainippon Printing Co Ltd 反射型液晶表示装置用カラーフィルタおよびその製造方法
JP2007119586A (ja) * 2005-10-27 2007-05-17 Canon Inc 液体組成物の製造方法、画像形成方法及び装置
WO2009144115A1 (fr) * 2008-05-28 2009-12-03 Basf Se Composition de filtre coloré rouge améliorée
JP2010174143A (ja) * 2009-01-29 2010-08-12 Fujifilm Corp 色素物質および色素物質分散物

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KR20100093137A (ko) * 2007-12-26 2010-08-24 도요 잉키 세이조 가부시끼가이샤 적색 칼라필터용 안료 조성물, 그의 제조방법, 그것을 사용한 착색 조성물, 및 컬러필터

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JPH10316876A (ja) * 1997-05-06 1998-12-02 Ciba Specialty Chem Holding Inc 新規なジケトピロロピロール組成物
JP2000089025A (ja) * 1998-09-14 2000-03-31 Fuji Photo Film Co Ltd カラーフィルター用感光性着色組成物
JP2003177231A (ja) * 2001-12-11 2003-06-27 Dainippon Printing Co Ltd 反射型液晶表示装置用カラーフィルタおよびその製造方法
JP2007119586A (ja) * 2005-10-27 2007-05-17 Canon Inc 液体組成物の製造方法、画像形成方法及び装置
WO2009144115A1 (fr) * 2008-05-28 2009-12-03 Basf Se Composition de filtre coloré rouge améliorée
JP2010174143A (ja) * 2009-01-29 2010-08-12 Fujifilm Corp 色素物質および色素物質分散物

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020075569A1 (fr) * 2018-10-11 2020-04-16 富士フイルム株式会社 Composition de coloration, film, filtre coloré ainsi que procédé de fabrication de celui-ci, structure, élément d'imagerie à l'état solide, et dispositif d'affichage d'image
JPWO2020075569A1 (ja) * 2018-10-11 2021-10-07 富士フイルム株式会社 着色組成物、膜、カラーフィルタ、カラーフィルタの製造方法、構造体、固体撮像素子及び画像表示装置
JP7143431B2 (ja) 2018-10-11 2022-09-28 富士フイルム株式会社 着色組成物、膜、カラーフィルタ、カラーフィルタの製造方法、構造体、固体撮像素子及び画像表示装置
WO2020241535A1 (fr) 2019-05-31 2020-12-03 富士フイルム株式会社 Capteur optique et dispositif de détection
WO2021039205A1 (fr) 2019-08-29 2021-03-04 富士フイルム株式会社 Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé
WO2021039253A1 (fr) 2019-08-30 2021-03-04 富士フイルム株式会社 Composition, film, filtre optique et procédé de production associé, élément d'imagerie à semi-conducteurs, capteur infrarouge et module de capteur
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge

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