JP2018028596A - Colored composition, colored cured film, color filter, display element and light receiving element - Google Patents

Abstract

To provide a coloring composition suitable for forming a colored cured film having a good balance of coloring power, luminance and contrast. A (A) coloring agent containing (a1) a phthalocyanine compound having no metal atom or halogen atom and (a2) an isoindoline compound, (B) a binder resin, and (C) a polymerizable compound. It is a coloring composition, Comprising: (a2) The coloring composition whose content rate of an isoindoline compound exceeds 0 mass% with respect to all the coloring agents, and is 10 mass% or less. Further, (a1) includes a phthalocyanine compound having no metal atom and halogen atom and (a2) an isoindoline compound, and (a2) the content of the isoindoline compound exceeds 10% by mass with respect to the total colorant. Provided are a colored cured film having a mass% or less, and a color filter, a display element and a light receiving element comprising the colored cured film. [Selection figure] None

Description

  The present invention relates to a colored composition, a colored cured film, a color filter, a display element, and a light receiving element. More specifically, the present invention relates to a transmissive or reflective color liquid crystal display element, solid-state imaging element, organic EL display element, and electronic paper. The present invention relates to a colored composition used for forming a colored cured film used in, etc., a colored cured film formed using the colored composition, a color filter including the colored cured film, a display element, and a light receiving element.

  In producing a color filter using a colored radiation-sensitive composition, a pigment-dispersed colored radiation-sensitive composition is applied on a substrate and dried, and then the dried coating film is irradiated with radiation in a desired pattern shape. There is known a method (for example, see Patent Documents 1 and 2) in which pixels of three primary colors of red, green, and blue are arranged on a substrate by irradiation (hereinafter referred to as “exposure”) and development. In addition, a method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (see, for example, Patent Document 3) is also known. Furthermore, a method for obtaining pixels of each color by an ink jet method using a pigment-dispersed colored resin composition is also known (for example, see Patent Document 4).

  As the colorant used for forming the pixel of the color filter, a pigment is often used from the viewpoint of heat resistance and solvent resistance. For example, when forming a green pixel, C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Green pigments such as CI Pigment Green 58 are used. However, since it is difficult to obtain a desired spectral spectrum using only the green pigment, the spectral spectrum is adjusted by combining a yellow pigment (for example, see Patent Document 5). However, together with the green pigment, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. When Pigment Yellow 185 is used, there is a problem that coloring power is low. In view of such a background, the present applicant has a good balance between coloring power and luminance, and a specific amount of a specific blue pigment and a specific yellow pigment as a coloring composition that is suitably used for forming a green cured film. The coloring composition containing was proposed (refer patent document 6).

JP-A-2-144502 JP-A-3-53201 JP-A-6-35188 JP 2000-310706 A JP 2010-26268 A Japanese Patent Laying-Open No. 2006-3288

  However, since the colored cured film formed from the colored composition of Patent Document 6 has a low contrast, it is useful for organic EL display elements and solid-state imaging devices that do not require contrast, but a liquid crystal display element that requires high contrast. It was difficult to apply for use.

  Therefore, the subject of this invention is providing the coloring composition suitable for formation of the colored cured film with the favorable balance of coloring power, a brightness | luminance, and contrast. Furthermore, the subject of this invention is providing the color filter, display element, and light receiving element which comprise the colored cured film formed using the said coloring composition, and this colored cured film.

  As a result of intensive studies, the present inventors have found that the above problem can be solved by using a certain amount of isoindoline compound together with a phthalocyanine compound having no metal atom and halogen atom.

That is, the present invention
(A1) a colorant comprising (a1) a phthalocyanine compound having no metal atom and halogen atom and (a2) an isoindoline compound,
(B) A colored composition containing a binder resin and (C) a polymerizable compound, wherein the content ratio of (a2) isoindoline compound is more than 0% by mass and less than 10% by mass with respect to the total colorant. A coloring composition is provided.

  The present invention also includes (a1) a phthalocyanine compound having no metal atom or halogen atom and (a2) an isoindoline compound, and (a2) the content of the isoindoline compound is 0% by mass with respect to the total colorant. The present invention provides a colored cured film that exceeds 10% by mass and a color filter, a display element, and a light receiving element comprising the colored cured film. The “colored cured film” as used herein means each color pixel, colored spacer, black matrix, etc. used in a display element or a light receiving element.

  If the coloring composition of this invention is used, the colored cured film with favorable balance of coloring power, a brightness | luminance, and contrast can be formed.

  Therefore, the colored composition of the present invention can be used very suitably for the production of solid-state imaging devices such as color liquid crystal display devices, organic EL display devices, display devices such as electronic paper, and CMOS image sensors.

Hereinafter, the present invention will be described in detail.
Coloring composition will be described in detail components of the colored composition of the present invention.

-(A) Colorant-
The colored composition of the present invention is essential to contain (a) a phthalocyanine compound having no metal atom and halogen atom and (a2) an isoindoline compound as (A) a colorant. The colored cured film formed using the colored composition of the present invention has a good balance of coloring power, luminance and contrast, and is therefore suitable for a color filter of a display element or a light receiving element, and particularly used for a liquid crystal display element. It is suitable for forming a green cured film of a color filter.

(A1) A phthalocyanine compound having no metal atom and no halogen atom is a compound having a phthalocyanine skeleton and containing no metal atom and no halogen atom. Examples of such compounds include phthalocyanine pigments and phthalocyanine dyes, but phthalocyanine pigments are preferred. I. Pigment Blue 16 is more preferable.
(A2) The isoindoline compound is a compound having an isoindoline skeleton, and examples of such a compound include isoindoline pigments and isoindoline dyes. Of these, isoindoline pigments are preferred. I. Pigment yellow 139, C.I. I. Pigment Yellow 185 is more preferable, and C.I. I. Pigment Yellow 185 is more preferable.

  In the colored composition of the present invention, it is essential that the content of the (a2) isoindoline compound is more than 0% by mass and 10% by mass or less based on the total colorant. The upper limit of the content ratio is preferably 7% by mass or less, more preferably 6% by mass or less, and still more preferably 2% by mass or less with respect to the total colorant. According to such an embodiment, a colored cured film having extremely good contrast can be formed.

  Moreover, it is preferable that the content rate of the (a1) phthalocyanine compound which does not have a metal atom and a halogen atom is 50-200 mass% with respect to (a2) isoindoline compound. According to such an embodiment, a colored cured film having excellent coloring power can be formed.

Furthermore, the total content of (a1) phthalocyanine compound having no metal atom and halogen atom and (a2) isoindoline compound is preferably more than 0% by mass and 15% by mass or less with respect to the total colorant. More preferably, it is more than 0% by mass and 12% by mass or less, more preferably more than 0% by mass and 9% by mass or less. According to such an embodiment, a colored cured film having excellent contrast can be formed.
In addition, the content rate of the (a1) phthalocyanine compound which does not have a metal atom and a halogen atom is more than 0 mass% normally and 15 mass% or less with respect to all the coloring agents.

  (A2) The content ratio of the isoindoline compound is usually more than 0% by mass and 20% by mass or less with respect to the all-yellow colorant, but preferably more than 0% by mass and 15% by mass or less. More preferably, the content exceeds 10% by mass, and more preferably the content exceeds 0% by mass and is 6% by mass or less. Here, the “yellow colorant” in the present invention includes (a2) an isoindoline compound, (a4) a quinophthalone compound described later, and (a5) a colorant exhibiting yellow among other colorants. And

  The coloring composition of this invention is used suitably for formation of a green cured film. In this case, the colored composition of the present invention preferably further contains (a3) a green colorant, and more preferably (a3) a green colorant and (a4) a quinophthalone compound.

(A3) As the green colorant, a known green pigment or green dye can be used. As the green pigment, a halogenated metal phthalocyanine pigment is preferable, and examples thereof include a halogenated copper phthalocyanine pigment, a halogenated zinc phthalocyanine pigment, and an aluminum halide phthalocyanine pigment.
Examples of the halogenated copper phthalocyanine pigment include C.I. I. Chlorinated copper phthalocyanine pigments such as CI Pigment Green 7; I. And chlorinated brominated copper phthalocyanine pigments such as CI Pigment Green 36. Examples of the halogenated zinc phthalocyanine pigment include C.I. I. Pigment green 58, C.I. I. Examples thereof include brominated chlorinated zinc phthalocyanine pigments such as CI Pigment Green 59.

  Among these, from the viewpoint of coloring power and brightness, a halogenated zinc phthalocyanine pigment is preferable, a brominated chlorinated zinc phthalocyanine pigment is more preferable, and C.I. I. Pigment green 58, C.I. I. Pigment Green 59 is more preferable.

  The (a4) quinophthalone compound is a compound having a quinophthalone skeleton. Specific examples thereof include C.I. I. Pigment Yellow 138 is preferable.

  For example, when the colored composition of the present invention is used for forming a green cured film of a color filter used for a display element or a light receiving element, the content ratio of each colorant is preferably as follows.

  (A3) It is preferable that the content rate of a green colorant is 30-80 mass% with respect to all the colorants.

  (A4) The upper limit of the content ratio of the quinophthalone compound is preferably 60% by mass or less, more preferably 45% by mass or less, still more preferably 35% by mass or less, and further preferably 15% by mass or more. Is preferable, and 25 mass% or more is more preferable. With such an embodiment, a colored and hardened film with high luminance can be formed.

  The coloring composition of the present invention may contain (a5) other colorants (pigments, dyes) other than those described above to the extent that the effects of the present invention are not affected. Specific examples include organic pigments and lake pigments classified as pigments and dyes classified as dyes in the color index (CI; issued by The Society of Dyers and Colorists).

  In the present invention, (a1) a phthalocyanine compound having no metal atom and a halogen atom, (a2) a pigment used as an isoindoline compound, and other pigments to be arbitrarily mixed, a recrystallization method, a reprecipitation method, It can also be used after being purified by a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof. Further, these pigments may be used by modifying the particle surface with a resin, if desired. Examples of the resin that modifies the particle surface of the pigment include vehicle resins described in JP-A No. 2001-108817, and various commercially available resins for dispersing pigments. The organic pigment may be used after the primary particles are refined by so-called salt milling. As a salt milling method, for example, a method disclosed in Japanese Patent Application Laid-Open No. 08-179111 can be employed.

  Further, in the present invention, (a1) a phthalocyanine compound having no metal atom and halogen atom, (a2) an isoindoline compound, and other colorant to be optionally mixed together with a known dispersant and dispersion aid. It can also be included.

  Known dispersants include, for example, urethane dispersants, polyethylene imine dispersants, polyoxyethylene alkyl ether dispersants, polyoxyethylene alkyl phenyl ether dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester dispersants. Dispersing agents, polyester-based dispersants, (meth) acrylic dispersants, and the like can be mentioned. Examples of commercially available products include Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 (above, manufactured by BYK (BYK)). (Meth) acrylic dispersants such as Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-1 2 (above, manufactured by BYK Corporation), urethane dispersants such as Solsperse 76500 (manufactured by Lubrizol Corporation), polyethyleneimine dispersants such as Solsperse 24000 (manufactured by Lubrizol Corporation), Ajispur Polyester dispersants such as BYK-LPN21324 (manufactured by BYK Corporation) can be used in addition to PB821, Azisper PB822, Azisper PB880, Azisper PB881 (manufactured by Ajinomoto Fine Techno Co., Ltd.).

  In this invention, a dispersing agent can be used individually or in mixture of 2 or more types.

  In the present invention, the content of the dispersant is preferably 5 to 300 parts by weight, more preferably 10 to 200 parts by weight, still more preferably 20 to 100 parts by weight, with respect to 100 parts by weight of the colorant (A). -50 mass parts is still more preferable.

  Examples of the dispersion aid include pigment derivatives. Specific examples of the pigment derivative include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivative of quinophthalone.

  (A) The content of the colorant is usually 5 to 70% by mass, preferably 5 to 60% by mass, more preferably 5% to 60% by mass in the solid content of the colored composition from the viewpoint of forming a pixel having high luminance and excellent coloring power. Is 10-50 mass%, and 20-50 mass% is particularly preferable. Here, solid content is components other than the solvent mentioned later.

-(B) Binder resin-
Although it does not specifically limit as (B) binder resin in this invention, It is preferable that it is resin which has acidic functional groups, such as a carboxyl group and a phenolic hydroxyl group. Among them, a polymer having a carboxyl group (hereinafter also referred to as “carboxyl group-containing polymer”) is preferable. For example, an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “unsaturated monomer”). And a copolymer of another copolymerizable ethylenically unsaturated monomer (hereinafter also referred to as “unsaturated monomer (b2)”). .

  Examples of the unsaturated monomer (b1) include (meth) acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono (meta ) Acrylate, p-vinylbenzoic acid and the like.

  These unsaturated monomers (b1) can be used alone or in admixture of two or more.

Moreover, as said unsaturated monomer (b2), for example,
N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide;
Aromatic vinyl compounds such as styrene, α-methylstyrene, p-hydroxystyrene, p-hydroxy-α-methylstyrene, p-vinylbenzylglycidyl ether, acenaphthylene;
Methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, polyethylene glycol (polymerization degree 2 10) methyl ether (meth) acrylate, polypropylene glycol (polymerization degree 2 to 10) methyl ether (meth) acrylate, polyethylene glycol (polymerization degree 2 to 10) mono (meth) acrylate, polypropylene glycol (polymerization degree 2 to 10) mono (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6] decan-8-yl (meth) acrylate, dicyclopentenyl (meth) acrylate Glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, ethylene oxide modified (meth) acrylate of paracumylphenol, glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, 3-[( (Meth) acrylic acid esters such as (meth) acryloyloxymethyl] oxetane, 3-[(meth) acryloyloxymethyl] -3-ethyloxetane;
Vinyl ethers such as cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3- (vinyloxymethyl) -3-ethyloxetane ;
Examples thereof include a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, and polysiloxane.

These unsaturated monomers (b2) can be used alone or in admixture of two or more.
In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50% by mass. More preferably, it is 10 to 40% by mass. By copolymerizing the unsaturated monomer (b1) in such a range, a colored composition excellent in alkali developability and storage stability can be obtained.

  Specific examples of the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) include, for example, JP-A-7-140654, JP-A-8-259876, and JP-A-10-31308. No. 10, JP-A-10-300902, JP-A-11-174224, JP-A-11-258415, JP-A-2000-56118, JP-A-2004-101728, etc. Coalescence can be mentioned.

  In the present invention, for example, JP-A-5-19467, JP-A-6-230212, JP-A-7-207211, JP-A-9-325494, JP-A-11-140144, As disclosed in Kaikai 2008-181095 and the like, a carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in the side chain can also be used as a binder resin.

  The binder resin in the present invention has a polystyrene-equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably Is 3,000 to 50,000. By setting it as such an aspect, the remaining-film rate of a film, a pattern shape, heat resistance, an electrical property, and the resolution can be improved further, and generation | occurrence | production of the dry foreign material at the time of application | coating can be suppressed at a high level.

  Further, the ratio (Mw / Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3. .0. In addition, Mn here says the number average molecular weight of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran).

  The binder resin in the present invention can be produced by a known method. For example, it is disclosed in Japanese Patent Application Laid-Open No. 2003-222717, Japanese Patent Application Laid-Open No. 2006-259680, International Publication No. 07/029871, etc. The structure, Mw, and Mw / Mn can be controlled by the method.

  In this invention, binder resin can be used individually or in mixture of 2 or more types.

  In this invention, content of binder resin is 10-1,000 mass parts normally with respect to 100 mass parts of (A) coloring agents, Preferably it is 20-500 mass parts, More preferably, it is 30-150 mass parts. . By setting it as such an aspect, in addition to the further improvement of coloring power and a brightness | luminance, alkali developability, the storage stability of a coloring composition, pattern shape, and chromaticity characteristic can be improved.

-(C) Polymerizable compound-
In the present invention, the polymerizable compound refers to a compound having two or more polymerizable groups. Examples of the polymerizable group include an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group. In the present invention, the polymerizable compound is preferably a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups.

  Specific examples of the compound having two or more (meth) acryloyl groups include a polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound and (meth) acrylic acid, a polyfunctional (meta) modified with caprolactone. ) Acrylate, alkylene oxide modified polyfunctional (meth) acrylate, polyfunctional urethane (meth) acrylate obtained by reacting hydroxyl-functional (meth) acrylate and polyfunctional isocyanate, hydroxyl-functional (meth) acrylate and acid anhydride The polyfunctional (meth) acrylate which has a carboxyl group obtained by making a product react can be mentioned.

  Here, examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; and 3 such as glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol. Mention may be made of aliphatic polyhydroxy compounds having a valence higher than that. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and glycerol diester. A methacrylate etc. can be mentioned. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of acid anhydrides include succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, dibasic acid anhydrides such as hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid. Examples thereof include dianhydrides and tetrabasic acid dianhydrides such as benzophenone tetracarboxylic dianhydride.

  Examples of the caprolactone-modified polyfunctional (meth) acrylate include compounds described in paragraphs [0015] to [0018] of JP-A No. 11-44955. The alkylene oxide-modified polyfunctional (meth) acrylate is at least one selected from bisphenol A di (meth) acrylate modified with at least one selected from ethylene oxide and propylene oxide, ethylene oxide and propylene oxide. Modified with at least one selected from trimethylolpropane tri (meth) acrylate, ethylene oxide and propylene oxide modified with at least one selected from modified isocyanuric acid tri (meth) acrylate, ethylene oxide and propylene oxide Pen modified with at least one selected from pentaerythritol tri (meth) acrylate, ethylene oxide and propylene oxide. Dipentaerythritol modified with at least one selected from dipentaerythritol penta (meth) acrylate, ethylene oxide and propylene oxide modified with at least one selected from taerythritol tetra (meth) acrylate, ethylene oxide and propylene oxide Examples include hexa (meth) acrylate.

  Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. The melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl-substituted triazine rings as a basic skeleton, and is a concept including melamine, benzoguanamine or a condensate thereof. Specific examples of the compound having two or more N-alkoxymethylamino groups include N, N, N ′, N ′, N ″, N ″ -hexa (alkoxymethyl) melamine, N, N, N ′. , N′-tetra (alkoxymethyl) benzoguanamine, N, N, N ′, N′-tetra (alkoxymethyl) glycoluril and the like.

  Among these polymerizable compounds, polyfunctional (meth) acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, caprolactone-modified polyfunctional (meth) acrylates, polyfunctional urethanes (Meth) acrylate, polyfunctional (meth) acrylate having a carboxyl group, N, N, N ′, N ′, N ″, N ″ -hexa (alkoxymethyl) melamine, N, N, N ′, N ′ -Tetra (alkoxymethyl) benzoguanamine is preferred. Among the polyfunctional (meth) acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, dipenta Among polyfunctional (meth) acrylates having a carboxyl group, erythritol hexaacrylate is obtained by reacting pentaerythritol triacrylate and succinic anhydride, and reacting dipentaerythritol pentaacrylate and succinic anhydride. The compound is particularly preferable in that the strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and background stains and film residues are hardly generated on the unexposed substrate and the light shielding layer.

In this invention, (C) polymeric compound can be used individually or in mixture of 2 or more types.
The content of the polymerizable compound (C) in the present invention is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, and 30 to 150 parts by mass with respect to 100 parts by mass of the (A) colorant. Is preferred. By adopting such an embodiment, curability and alkali developability are further improved, and in addition to further improvement in coloring power and brightness, background stains, film residue, etc. on the unexposed substrate or on the light shielding layer Occurrence can be suppressed at a high level.

-(D) Photopolymerization initiator-
The coloring composition of the present invention can contain a photopolymerization initiator. Thereby, radiation sensitivity can be provided to a coloring composition. The photopolymerization initiator used in the present invention is a compound that generates an active species capable of initiating polymerization of the polymerizable compound by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray.

  Examples of such photopolymerization initiators include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketone compounds, polynuclear quinone compounds, A diazo compound, an imide sulfonate compound, etc. can be mentioned.

  In this invention, a photoinitiator can be used individually or in mixture of 2 or more types. The photopolymerization initiator is preferably at least one selected from the group consisting of a thioxanthone compound, an acetophenone compound, a biimidazole compound, a triazine compound, and an O-acyloxime compound.

  Among the preferred photopolymerization initiators in the present invention, specific examples of the thioxanthone compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2, 4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone and the like can be mentioned.

  Specific examples of the acetophenone compound include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4- And morpholinophenyl) butan-1-one and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

  Specific examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′- Bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 Examples include ', 5,5'-tetraphenyl-1,2'-biimidazole.

  In addition, when using a biimidazole compound as a photoinitiator, using a hydrogen donor together is preferable at the point which can improve a sensitivity. The term “hydrogen donor” as used herein means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure. Examples of the hydrogen donor include mercaptan hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole, 4,4′-bis (dimethylamino) benzophenone, and 4,4′-bis (diethylamino) benzophenone. Mention may be made of amine hydrogen donors. In the present invention, hydrogen donors can be used alone or in admixture of two or more, but one or more mercaptan hydrogen donors and one or more amine hydrogen donors are used in combination. Is preferable in that the sensitivity can be further improved.

  Specific examples of the triazine compound include compounds described in paragraphs [0063] to [0065] of JP-B-57-6096 and JP-A-2003-238898.

  Specific examples of the O-acyloxime compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), ethanone, 1- [9-ethyl- 6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- (2-methyl-4-tetrahydrofuranylmethoxybenzoyl) ) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- {2-methyl-4- (2,2-dimethyl-1,3- And dioxolanyl) methoxybenzoyl} -9H-carbazol-3-yl]-, 1- (O-acetyloxime). As commercially available O-acyloxime compounds, NCI-831, NCI-930 (above, manufactured by ADEKA Corporation), DFI-020, DFI-091 (above, manufactured by Daito Chemix Corporation), and the like can also be used. .

  In this invention, when using photoinitiators other than biimidazole compounds, such as an acetophenone compound, a sensitizer can also be used together. Examples of such a sensitizer include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, and 4-dimethyl. Ethyl aminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, etc. Can be mentioned.

  In the present invention, the content of (D) the photopolymerization initiator is preferably 0.01 to 120 parts by weight, more preferably 1 to 100 parts by weight, with respect to 100 parts by weight of (C) the polymerizable compound. More preferred is 40 parts by weight. By setting it as such an aspect, sclerosis | hardenability and a film characteristic can be improved more and coloring power and a brightness | luminance can be improved further.

-(E) Solvent-
The colored composition of the present invention contains the above components (A) to (C) and other components that are optionally added, but is usually prepared as a liquid composition by blending a solvent.

  (E) As a solvent, as long as (A)-(C) component and other components which comprise a coloring composition are disperse | distributed or melt | dissolved, and it does not react with these components, but has moderate volatility. Can be appropriately selected and used.

Among such solvents, for example
Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n- Butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, di Propylene glycol mono Chirueteru, dipropylene glycol mono -n- propyl ether, dipropylene glycol mono -n- butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl (poly) alkylene glycol monoalkyl ethers such as ether;
Lactic acid alkyl esters such as methyl lactate and ethyl lactate;
(Cyclo) alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol, cyclohexanol;
Keto alcohols such as diacetone alcohol;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, (Poly) alkylene glycol monoalkyl ether acetates such as 3-methyl-3-methoxybutyl acetate;
Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran;
Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone;
Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate;
Alkoxycarboxylic esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, 3-methyl-3-methoxybutylpropionate ;
Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-butyric acid Other esters such as -propyl, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate;
Aromatic hydrocarbons such as toluene and xylene;
Examples include amides or lactams such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone.

  Of these solvents, (poly) alkylene glycol monoalkyl ethers, lactic acid alkyl esters, (poly) alkylene glycol monoalkyl ether acetates, and other ethers from the viewpoints of solubility, pigment dispersibility, coatability, etc. , Ketones, diacetates, alkoxycarboxylic acid esters, and other esters are preferred, especially propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether Acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-hept Non, 3-heptanone, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3- Methyl-3-methoxybutylpropionate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate, Ethyl pyruvate and the like are preferable.

  In this invention, a solvent can be used individually or in mixture of 2 or more types.

  (E) Although content of a solvent is not specifically limited, The quantity from which the total density | concentration of each component except the solvent of the coloring composition becomes 5-50 mass% is preferable, and it is 10-40 mass%. Is more preferred. By setting it as such an aspect, the coloring composition with favorable applicability | paintability and stability can be obtained.

-Additives-
The coloring composition of this invention can also contain a various additive as needed.

  Examples of additives include fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylates); surfactants such as fluorosurfactants and silicon surfactants; vinyl Trimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxy Silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyl Dimethoxysilane, 3-chloropropi Adhesion promoters such as trimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane; 2,2-thiobis (4-methyl-6-tert-butylphenol), 2,6-di- t-butylphenol, pentaerythritol tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], 3,9-bis [2- [3- (3-t-butyl-4-hydroxy) -5-methylphenyl) -propionyloxy] -1,1-dimethylethyl] -2,4,8,10-tetraoxa-spiro [5 · 5] undecane, thiodiethylenebis [3- (3,5-di- antioxidants such as t-butyl-4-hydroxyphenyl) propionate]; 2- (3-t-butyl-5-methyl-2-hydroxy Nyl) -5-chlorobenzotriazole, alkoxybenzophenones, etc .; anti-aggregation agents such as sodium polyacrylate; malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, 2-aminoethanol 3-amino-1-propanol, 5-amino-1-pentanol, 3-amino-1,2-propanediol, 2-amino-1,3-propanediol, 4-amino-1,2-butanediol Residue improving agents such as succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ω-carboxypolycaprolactone mono (meth) acrylate, etc. An improving agent etc. can be mentioned.

  The coloring composition of the present invention can be prepared by an appropriate method. Examples of the preparation method include (A) to (C) components together with (E) a solvent and other components optionally added. , Can be prepared by mixing. Among them, (A1) a colorant containing (a1) a phthalocyanine compound having no metal atom and halogen atom and (a2) an isoindoline compound (E) in a solvent in the presence of a dispersant, optionally (B) A part of the binder resin, for example, a bead mill, a roll mill, etc., mixed and dispersed while being pulverized to obtain a colorant dispersion, and then the (C) polymerizable compound and, if necessary, the colorant dispersion (B) a binder resin, (D) a photopolymerization initiator, an additional (E) solvent and other components are preferably added and mixed. In addition, (a1) a phthalocyanine compound having no metal atom and halogen atom is used in (E) a solvent in the presence of a dispersant, optionally with (B) a part of a binder resin, for example, using a bead mill, a roll mill or the like. Then, a colorant dispersion (1) is prepared by mixing and dispersing while pulverizing, and separately (a2) isoindoline compound in (E) solvent in the presence of a dispersant and optionally (B) binder resin. Along with a part, for example, a bead mill, a roll mill or the like is used to prepare a colorant dispersion (2) by mixing and dispersing while pulverizing, and the colorant dispersion (1) and the colorant dispersion (2) are ( A method of preparing by adding and mixing (C) a polymerizable compound and, if necessary, (B) a binder resin, (D) a photopolymerization initiator, an additional (E) solvent and other components is also preferred.

Colored cured film and method for producing the same The colored cured film of the present invention includes (a1) a phthalocyanine compound having no metal atom and a halogen atom and (a2) an isoindoline compound, and (a2) a content ratio of the isoindoline compound. The content is more than 0% by mass and 10% by mass or less based on the total colorant, and can be formed using the colored composition of the present invention. As the colored cured film of the present invention, for example, there is a green cured film used for a color filter constituting a display element or a solid-state imaging element. In particular, by using the colored cured film of the present invention for a liquid crystal display element, a color filter or a liquid crystal display element having a good balance of coloring power, luminance, and contrast can be produced. In other words, a color filter or a liquid crystal display element having a good balance between luminance and contrast can be manufactured using a thin film.

  Hereinafter, a colored cured film used for a color filter and a method for forming the same will be described.

  As a method for forming the colored cured film constituting the color filter, the following method is first exemplified. First, a light shielding layer (black matrix) is formed on the surface of the substrate so as to divide a portion where pixels are formed, if necessary. Next, for example, after applying a green liquid composition of the radiation-sensitive colored composition of the present invention on the substrate, pre-baking is performed to evaporate the solvent, thereby forming a coating film. Subsequently, after exposing this coating film through a photomask, it develops using an alkali developing solution, and the unexposed part of a coating film is dissolved and removed. Thereafter, post-baking is performed to form a pixel array in which green pixel patterns (colored cured films) are arranged in a predetermined arrangement.

  Subsequently, each radiation-sensitive colored composition of red or blue is used, and the radiation-sensitive colored composition is applied, pre-baked, exposed, developed, and post-baked in the same manner as described above, so that the red pixel array and blue Are sequentially formed on the same substrate. Thereby, a color filter in which pixel arrays of the three primary colors of red, green and blue are arranged on the substrate is obtained. However, in the present invention, the order of forming pixels of each color is not limited to the above.

  A black matrix can be formed by forming a metal thin film such as chromium formed by sputtering or vapor deposition into a desired pattern using a photolithographic method. It can also be formed in the same manner as in the case of forming the above-mentioned pixel using a sexually colored composition.

  Examples of the substrate used when forming the colored cured film include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.

  In addition, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.

  When applying the radiation-sensitive coloring composition to the substrate, an appropriate coating method such as spraying, roll coating, spin coating (spin coating), slit die coating (slit coating), bar coating, etc. In particular, it is preferable to employ a spin coating method or a slit die coating method.

The pre-baking is usually about 70 to 110 ° C. for about 1 to 10 minutes.
The coating thickness is usually 0.6 to 8 μm, preferably 1.2 to 5 μm, as the film thickness after drying.

  Examples of the radiation light source used when forming at least one selected from the pixel and the black matrix include, for example, a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, and a low pressure. Examples thereof include a lamp light source such as a mercury lamp, and a laser light source such as an argon ion laser, a YAG laser, a XeCl excimer laser, and a nitrogen laser. An ultraviolet LED can also be used as the exposure light source. The wavelength is preferably radiation in the range of 190 to 450 nm.

In general, the exposure dose of radiation is preferably 10 to 10,000 J / m ² .

Examples of the alkali developer include sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-. An aqueous solution of undecene, 1,5-diazabicyclo- [4.3.0] -5-nonene or the like is preferable.
For example, an appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline developer. In addition, it is usually washed with water after alkali development.

  As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied. The development conditions are preferably 5 to 300 seconds at room temperature.

The post-baking conditions are usually 180 to 280 ° C. and about 10 to 60 minutes.
The film thickness of the pixel thus formed is usually 0.5 to 5 μm, preferably 1.0 to 3 μm.

  Further, as a second method for forming a colored cured film constituting a color filter, a method for obtaining pixels of each color by an ink jet method disclosed in JP-A-7-318723, JP-A-2000-310706, etc. Can be adopted. In this method, first, a partition having a light shielding function is formed on the surface of the substrate. Next, for example, a green liquid composition of the thermosetting coloring composition of the present invention is discharged into the formed partition wall by an inkjet apparatus, and then prebaked to evaporate the solvent. Next, this coating film is exposed as necessary and then cured by post-baking to form a green pixel pattern.

  Subsequently, red or blue thermosetting coloring compositions are used to sequentially form a red pixel pattern and a blue pixel pattern on the same substrate in the same manner as described above. Thereby, a color filter in which pixel patterns of the three primary colors of red, green and blue are arranged on the substrate is obtained. However, in the present invention, the order of forming pixels of each color is not limited to the above.

  In addition, since the partition plays not only a light shielding function but also a function for preventing the color mixing of the thermosetting coloring compositions discharged in the respective sections, it is compared with the black matrix used in the first method described above. The film thickness is thick. Therefore, a partition is normally formed using a black radiation sensitive composition.

  The substrate used for forming the colored cured film, the light source of radiation, and the pre-baking and post-baking methods and conditions are the same as in the first method described above. In this way, the film thickness of the pixel formed by the ink jet method is approximately the same as the height of the partition wall.

  A protective film is formed on the pixel pattern thus obtained as necessary, and then a transparent conductive film is formed by sputtering. After forming the transparent conductive film, a spacer can be further formed to form a color filter. The spacer is usually formed using a radiation-sensitive composition, but may be a light-shielding spacer (black spacer). In this case, a colored radiation-sensitive composition in which a black colorant is dispersed is used.

  Since the color filter including the colored cured film of the present invention formed in this way has extremely high coloring power, luminance, and contrast, a color liquid crystal display element, a color imaging tube element, a color sensor, an organic EL display element, and electronic paper It is extremely useful for such as.

Color filter The color filter of the present invention comprises the colored cured film of the present invention, and can be used for a display element and a light receiving element as described later.

Display element The display element of the present invention comprises the colored cured film of the present invention. Examples of the display element include a color liquid crystal display element, an organic EL display element, and electronic paper.
The color liquid crystal display element provided with the colored cured film of the present invention may be a transmissive type or a reflective type, and can take an appropriate structure. For example, the color filter is formed on a substrate different from the driving substrate on which the thin film transistor (TFT) is arranged, and the driving substrate and the substrate on which the color filter is formed are opposed to each other with a liquid crystal layer interposed therebetween. Further, a substrate in which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate in which an ITO (tin-doped indium oxide) electrode is formed are a liquid crystal layer. It is also possible to adopt a structure that is opposed to each other. The latter structure has the advantage that the aperture ratio can be remarkably improved, and a bright and high-definition liquid crystal display element can be obtained. When the latter structure is adopted, the black matrix and the black spacer may be formed on either the substrate side on which the color filter is formed or the substrate side on which the ITO electrode is formed.

  The color liquid crystal display element including the colored cured film of the present invention can include a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). As the white LED, for example, a white LED that obtains white light by color mixing by combining a red LED, a green LED, and a blue LED, a white LED that obtains white light by color mixing by combining a blue LED, a red LED, and a green phosphor, and a blue LED White LED that obtains white light by mixing colors, red LED and green light emitting phosphor, white LED that obtains white light by mixing colors of blue LED and YAG phosphor, blue LED, orange light emitting phosphor and green light emitting fluorescence A white LED that obtains white light by color mixing by combining the body, a white LED that obtains white light by color mixing by combining an ultraviolet LED, a red light emitting phosphor, a green light emitting phosphor, and a blue light emitting phosphor can be exemplified.

  The color liquid crystal display element having the colored cured film of the present invention includes TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, IPS (In-Plane Switching) type, VA (Vertical Alignment) type, OCB (Optical). An appropriate liquid crystal mode such as a Compensated Birefringence type is applicable.

Moreover, the organic EL display element provided with the colored cured film of the present invention can take an appropriate structure, and examples thereof include a structure disclosed in JP-A-11-307242.
Moreover, the electronic paper provided with the colored cured film of the present invention can take an appropriate structure, and examples thereof include a structure disclosed in Japanese Patent Application Laid-Open No. 2007-41169.

Light receiving element The light receiving element of the present invention comprises the colored cured film of the present invention. An example of the light receiving element is a solid-state imaging element.
The solid-state imaging device of the present invention can take an appropriate structure. For example, as one embodiment, by using the colored composition of the present invention to form a colored pixel (colored cured film) on a semiconductor substrate such as a CMOS substrate by the same operation as described above, in particular, spectral characteristics. In addition, a solid-state imaging device having excellent color separation can be manufactured.

  Hereinafter, the embodiment of the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples.

<Synthesis of binder resin>
Synthesis example 1
A flask equipped with a condenser and a stirrer was charged with 100 parts by mass of propylene glycol monomethyl ether acetate (hereinafter also referred to as “PGMEA”) and purged with nitrogen. Heat to 80 ° C. and at the same temperature, PGMEA 100 parts by mass, benzyl methacrylate 25 parts by mass, styrene 10 parts by mass, N-phenylmaleimide 20 parts by mass, glycerol monomethacrylate 5 parts by mass, methacrylic acid 10 parts by mass, ω-carboxyl A mixed solution of 30 parts by mass of polycaprolactone monoacrylate and 3 parts by mass of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour, and polymerization was carried out for 3 hours while maintaining this temperature. Thereafter, the temperature of the reaction solution was raised to 100 ° C., and further polymerized for 1 hour to obtain a binder resin solution (solid content concentration: 40% by mass). The obtained binder resin had Mw of 9,800 and Mn of 6,000. This binder resin solution is referred to as “binder resin solution (B-1)”.

Synthesis example 2
A flask equipped with a condenser and a stirrer was charged with 3 parts by mass of 2,2′-azobisisobutyronitrile and 200 parts by mass of PGMEA, followed by 12 parts by mass of N-phenylmaleimide, 10 parts by mass of styrene, and 10 parts by mass of methacrylic acid. Then, 56 parts by mass of (3-ethyloxetane-3-yl) methyl methacrylate and 5 parts by mass of pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by Sakai Chemical Industry Co., Ltd.) were charged and purged with nitrogen. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 80 ° C., and this temperature was maintained for 3 hours for polymerization. Thereafter, the temperature of the reaction solution was raised to 100 ° C., and further polymerized for 1 hour to obtain a binder resin solution (solid content concentration: 34% by mass). The obtained binder resin had Mw of 9,700 and Mn of 5,700. This binder resin solution is referred to as “binder resin solution (B-2)”.

Synthesis example 3
A flask equipped with a condenser and a stirrer was charged with 3 parts by mass of 2,2′-azobisisobutyronitrile and 140 parts by mass of PGMEA, followed by 15 parts by mass of methacrylic acid, 15 parts by mass of 2-hydroxyethyl methacrylate, and methoxyethyl methacrylate. 30 parts by mass, 40 parts by mass of isobutyl methacrylate, and 5 parts by mass of pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by Sakai Chemical Industry Co., Ltd.) were charged and the atmosphere was replaced with nitrogen. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 80 ° C., and this temperature was maintained for 3 hours for polymerization. Thereafter, the temperature of the reaction solution was raised to 100 ° C., and further polymerized for 1 hour to obtain a binder resin solution (solid content concentration: 45 mass%). The obtained binder resin had Mw of 7,900 and Mn of 5,200. This binder resin solution is referred to as “binder resin solution (B-3)”.

<Preparation of colorant dispersion>
Preparation Example 1
As a coloring agent, C.I. I. 12 parts by weight of Pigment Blue 59, 13 parts by weight of BYK-LPN21116 (produced by Big Chemie, solid concentration = 40% by weight) as a dispersant, and 10 parts by weight (solid content) of a binder resin solution (B-1) as a binder resin Concentration of 40% by mass), 57 parts by mass of PGMEA and 8 parts by mass of propylene glycol monoethyl ether as a solvent were mixed and dispersed by a bead mill for 12 hours to prepare a colorant dispersion (G1).

Preparation Examples 2-6
In Preparation Example 1, the type and amount of each component were changed as shown in Table 1 to prepare colorant dispersions (G2), (Y1) to (Y3), and (B1).

In Table 1, each component is as follows.
PG59: C.I. I. Pigment Green 59
PG58: C.I. I. Pigment Green 58
PY138: C.I. I. Pigment Yellow 138
PY150: C.I. I. Pigment Yellow 150
PY185: C.I. I. Pigment Yellow 185
PB16: C.I. I. Pigment Blue 16
LPN21116: BYK-LPN21116 ((meth) acrylic dispersant, manufactured by Big Chemie, solid content concentration = 40% by mass)
PGEE: Propylene glycol monoethyl ether

<Preparation and evaluation of coloring composition>
Example 1
Colorant dispersion (G1) 148.7 parts by mass, colorant dispersion (Y1) 61.3 parts by mass, colorant dispersion (Y3) 4.4 parts by mass and colorant dispersion (B1) 4 .4 parts by weight, 10.3 parts by weight of binder resin solution (B-1) and 12.2 parts by weight of binder resin solution (B-2) as binder resin, dipentaerythritol pentaacrylate and dipentaerythritol hexa as polymerizable compounds Mixture of acrylates (Nippon Kayaku Co., Ltd., trade name KAYARAD DPHA) 17.0 parts by mass, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator (BASF, trade name Irgacure 369) 1.6 parts by mass and NCI-930 (manufactured by ADEKA Corporation) 1.6 parts by mass, fluorine-based material Megafac F-554 (manufactured by DIC Corporation) 0.15 parts by mass as an activator, and PGMEA 153.4 parts by mass, 3-methoxybutyl acetate 63.7 parts by mass and dipropylene glycol methyl ether acetate 21.3 A colored composition (GS-1) having a solid content concentration of 15% by mass was prepared by mixing parts by mass. In addition, the coloring agent density | concentration with respect to the total solid is 35 mass%.

Evaluation of Film Thickness and Luminance The colored composition (GS-1) was applied on a glass substrate using a slit die coater, and then pre-baked on a 90 ° C. hot plate for 1 minute to form a coating film. The same operation was performed by changing the coating conditions of the slit die coater to form three coating films having different film thicknesses. Then, after cooling these substrates to room temperature, the coating film on the substrates was exposed to radiation containing each wavelength of 365 nm, 405 nm, and 436 nm at 600 J / m ² without using a high pressure mercury lamp. Exposed in quantity. After that, shower development was performed on these substrates by discharging a developer composed of a 0.04% potassium hydroxide aqueous solution at 23 ° C. at a development pressure of 1 kgf / cm ² (nozzle diameter 1 mm). Thereafter, these substrates were washed with ultrapure water, air-dried, and further post-baked in a clean oven at 230 ° C. for 20 minutes to produce three substrates on which a green cured film was formed.
Using the color analyzer (MCPD2000 manufactured by Otsuka Electronics Co., Ltd.), the chromaticity coordinates (x, y) and the stimulus value in the CIE color system with a C light source and a 2-degree visual field for the three green cured films obtained. (Y) was measured. From the measurement result, the stimulus value (Y) when the chromaticity coordinate value y = 0.635 was obtained. Moreover, the film thickness of the obtained cured film was measured using the alpha step IQ made from KLA-Tencor. The evaluation results are shown in Table 3. It can be said that the greater the stimulus value (Y), the higher the luminance, and the thinner the film thickness, the greater the coloring power. The chromaticity coordinate value x = 0.182. If the film thickness is larger than 3.0 μm, it is judged to be unsuitable for practical use.

Evaluation of contrast The substrate on which the cured film is formed is sandwiched between two deflecting plates, and the front deflecting plate is rotated while irradiating with a fluorescent lamp (wavelength range of 380 to 780 nm) from the back side, and the luminance meter LS-100 ( The maximum value and the minimum value of the light intensity transmitted by Minolta Co., Ltd. were measured. And about each cured film, the value which remove | divided the maximum value by the minimum value was made into the contrast ratio. From the measurement result, the contrast ratio at the chromaticity coordinate value y = 0.635 is obtained. The case where the contrast ratio is 8000 or more is “A”, the case where it is 7000 or more and less than 8000 is “B”, and the case where it is 6000 or more and less than 7000 The case of “C” and less than 6000 was evaluated as “D”. The evaluation results are shown in Table 3. Note that the larger the numerical value, the better the contrast ratio.

Examples 2-7 and Comparative Examples 1-4
In Example 1, the kind and quantity of each component were changed as shown in Table 2, and colored compositions (GS-2) to (GS-11) were prepared. In the colored compositions (GS-2) to (GS-11), the colorant concentration relative to the total solid content is 35% by mass.
Subsequently, it replaced with coloring composition (GS-1), and was the same as Example 1 except having used coloring compositions (GS-2)-(GS-6) and (GS-8)-(GS-10). And evaluated. In both cases, the chromaticity coordinate value x = 0.182. The evaluation results are shown in Table 3.
Moreover, it replaces with coloring composition (GS-1), and uses chromaticity coordinate value y = 0.550 like Example 1 except having used coloring composition (GS-7) and (GS-11). The stimulation value (Y) was obtained. Note that the chromaticity coordinate value x = 0.216. The evaluation results are shown in Table 4.

In Table 2, each component is as follows.
C-1: Mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., trade name KAYARAD DPHA)
D-1: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (manufactured by BASF, trade name Irgacure 369)
D-2: NCI-930 (manufactured by ADEKA Corporation)
F-1: Megafuck F-554 (manufactured by DIC Corporation)
MBA: 3-methoxybutyl acetate DPMA: dipropylene glycol methyl ether acetate

In Tables 3 to 4, “(a2) × 100 / (A)” indicates the content ratio of the (a2) isoindoline compound to the total colorant, and “(a1) × 100 / (a2)” ) The content ratio of (a1) phthalocyanine compound having no metal atom and halogen atom to the isoindoline compound is shown. Furthermore, “[(a1) + (a2)] × / (A)” is the total content of (a1) a phthalocyanine compound having no metal atom and no halogen atom and (a2) an isoindoline compound with respect to all colorants. “(A2) × 100 / (all yellow colorant)” indicates the content ratio of the (a2) isoindoline compound to the all yellow colorant.
From Tables 3 and 4, it can be said that the green cured film formed using the colored compositions (GS-1) to (GS-7) has a good balance of coloring power, luminance and contrast.

Claims (10)

(A1) a coloring composition containing (A) a colorant, (B) a binder resin, and (C) a polymerizable compound containing a phthalocyanine compound having no metal atom and halogen atom and (a2) an isoindoline compound. There,
(A2) The coloring composition whose content rate of an isoindoline compound exceeds 0 mass% with respect to all the coloring agents, and is 10 mass% or less.   The coloring composition according to claim 1, wherein the content ratio of (a1) a phthalocyanine compound having no metal atom and no halogen atom is 50 to 200% by mass relative to (a2) an isoindoline compound.   The total content of (a1) a phthalocyanine compound having no metal atom and halogen atom and (a2) an isoindoline compound is more than 0% by mass and 15% by mass or less based on the total colorant. The coloring composition as described in 2.   (A1) A phthalocyanine compound having no metal atom or halogen atom is C.I. I. Pigment Blue 16 and (a2) the isoindoline compound is C.I. I. The coloring composition according to any one of claims 1 to 3, comprising Pigment Yellow 185.   The colored composition according to any one of claims 1 to 4, wherein the colorant further comprises (a3) a green colorant and (a4) a quinophthalone compound.   (A2) The coloring composition of any one of Claims 1-5 whose content rate of an isoindoline compound exceeds 0 mass% with respect to all the yellow colorants, and is 15 mass% or less.   (A1) a phthalocyanine compound having no metal atom or halogen atom and (a2) an isoindoline compound, and (a2) the content ratio of the isoindoline compound is more than 0% by mass and 10% by mass with respect to the total colorant A colored cured film that is:   A color filter comprising the colored cured film according to claim 7.   A display element provided with the colored cured film according to claim 7. A light receiving element comprising the colored cured film according to claim 7.