JP2018055095A - Photosensitive composition for color filters and color filter substrate prepared therewith - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a photosensitive composition for color filters that can prevent color migration in which a colorant moves to an adjacent layer.SOLUTION: A photosensitive composition for color filters contains a radical polymerizable compound and a compound represented by general formula (1) (where, R-Rare a hydrogen atom, or a monovalent organic group having an unsaturated double bond or an epoxy group, where at least one of R-Ris a monovalent organic group having an unsaturated double bond or an epoxy group).SELECTED DRAWING: None

Description

  The present invention relates to a photosensitive composition for a color filter, a color filter substrate using the same, a method for producing the same, and a display device.

  Liquid crystal display devices are used in various applications such as televisions, notebook computers, personal digital assistants, smartphones, digital cameras, etc., taking advantage of characteristics such as light weight, thinness, and low power consumption. The liquid crystal display device is required to have an optimum color of 3 to 6 primary colors according to the application, and a color filter substrate that bears various color performances is used.

  A color filter is generally produced by a photolithography method using a color filter composition containing a colorant, and the pixel is formed by applying the color filter composition on a substrate, and exposing and developing the color filter. Form. The colorant used in the color filter composition is generally a pigment, but in recent years, a color filter composition containing a dye has been developed in order to increase the transmittance. A color filter composition containing a dye has a problem of color transfer that causes the dye to move to an adjacent pixel. Therefore, as a technique for suppressing the phenomenon in which the colored radiation-sensitive composition of another color penetrates into the previously formed pixel and the color purity of the pixel is reduced, a dye, a photopolymerizable compound, a photopolymerization initiator, and A colored radiation-sensitive composition containing a specific nonionic surfactant has been proposed (see, for example, Patent Document 1). However, even if this technique is used, the effect of suppressing color migration is still insufficient.

JP 2014-199436 A

  In view of such a situation, an object of the present invention is to provide a photosensitive composition for a color filter capable of suppressing a color transfer in which a coloring material moves to an adjacent layer.

  That is, this invention is a photosensitive composition for color filters containing a radically polymerizable compound and the compound represented by following General formula (1).

In the general formula (1), R ^{1 to} R ⁴ represent a hydrogen atom or a monovalent organic group represented by the following structural formula (2) or the following structural formula (3). However, at least one of R ^{1 to} R ⁴ represents a monovalent organic group represented by the following structural formula (2).

  Moreover, this invention is a photosensitive composition for color filters containing the radically polymerizable compound which has a 3 or more (meth) acryloyloxy group and a carboxyl group, and the compound represented by following General formula (5).

In the general formula (5), R ^{5 to} R ⁸ represent a hydrogen atom or a monovalent organic group represented by the following structural formula (3). However, at least one of R ^{5 to} R ⁸ represents a monovalent organic group represented by the following structural formula (3).

  According to the photosensitive composition for a color filter of the present invention, it is possible to suppress a color shift in which a color material moves to an adjacent layer in a color filter.

  The photosensitive composition for color filters of the first aspect of the present invention contains a radically polymerizable compound and a compound represented by the general formula (1). Moreover, the photosensitive composition for color filters of the 2nd aspect of this invention is represented by the said general formula (5) and the radically polymerizable compound which has three or more (meth) acryloyloxy groups and a carboxyl group. Contains compounds. The radically polymerizable compound is a component that imparts radical polymerizability to the composition, and the compound represented by the general formula (1) or (5) has a color transfer that causes the colorant to move to the adjacent layer in the color filter. It is a component to suppress. The color transfer referred to here refers to a phenomenon in which a color material in a pixel formed later penetrates into a pixel formed earlier.

  The first aspect of the present invention will be described. The photosensitive composition for color filters of the first aspect of the present invention contains a radically polymerizable compound and a compound represented by the following general formula (1). Since the compound represented by the following general formula (1) has radical polymerizability, the color filter photosensitive composition of the first aspect of the present invention can form a pattern by an exposure / development process described later. it can. That is, in the photosensitive composition for a color filter of the first aspect of the present invention, the compound represented by the following general formula (1) has an effect of imparting radical polymerizability to the composition, and color transfer in the color filter. It has both an inhibitory effect. In addition, due to the interaction between the nitrogen atom contained in the condensed ring skeleton of the compound having the structure represented by the following general formula (1) and the carboxyl group contained in the radical polymerizable compound described later, the high density of the film by heating It is presumed that the process proceeds, and even a heat treatment at a low temperature of 150 ° C. or lower can be easily cured.

In the general formula (1), R ^{1 to} R ⁴ represent a hydrogen atom or a monovalent organic group represented by the following structural formula (2) or the following structural formula (3). However, at least one of R ^{1 to} R ⁴ represents a monovalent organic group represented by the following structural formula (2).

At least one of R ^{1 to} R ⁴ represents a monovalent organic group represented by the structural formula (2). When at least one is a monovalent organic group represented by the structural formula (2), radical polymerizability can be imparted. From the viewpoint of radical polymerizability by light irradiation and patterning properties, it is preferable to have two or more monovalent organic groups represented by the above structural formula (2) among R ^{1 to} R ⁴ , and to have three or more. Is more preferable, and it is more preferable to have four. A compound in which all of R ^{1 to} R ⁴ represent a monovalent organic group represented by the structural formula (2) is represented by the following structural formula (4).

In the general formula (1), R ^{1 to} R ⁴ are a monovalent organic group represented by the structural formula (2), a hydrogen atom and / or a monovalent represented by the structural formula (3). You may have an organic group.

  As a compound represented by General formula (1), the compound which has the following structures is mentioned, for example. Two or more of these may be contained.

  The content of the compound represented by the general formula (1) in the photosensitive composition for a color filter of the present invention is a solid content excluding the color material of the photosensitive composition for a color filter from the viewpoint of further suppressing color transfer. Among them, 5% by mass or more is preferable, 10% by mass or more is more preferable, and 15% by mass or more is more preferable. On the other hand, the content of the compound represented by the general formula (1) is preferably 40% by mass or less in the solid content excluding the color material of the photosensitive composition for a color filter from the viewpoint of further suppressing color transfer. The mass% or less is more preferable.

  The photosensitive composition for color filters of the first aspect of the present invention contains a radical polymerizable compound. A radically polymerizable compound refers to a compound having an unsaturated hydrocarbon group. However, the compound represented by the general formula (1) is excluded. Examples of the unsaturated hydrocarbon group include a (meth) acryloyl group, a vinyl group, and a maleimide group. You may have 2 or more types of these.

  Examples of the radical polymerizable compound include dipentaerythritol penta (meth) acrylate, tetratrimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth). ) Ethylene oxide modified products such as acrylate or propylene oxide modified products, styrene derivatives, polyfunctional maleimide compounds, poly (meth) acrylate carbamates, 1,6-hexanediol (meth) acrylate esters of adipic acid, propylene oxide phthalate anhydride ( (Meth) acrylic acid ester, trimellitic acid diethylene glycol (meth) acrylic acid ester, rosin modified epoxy di (meth) acrylate, alkyd modified ( ) Oligomers such as acrylate, tripropylene glycol di (meth) acrylate, bifunctional (meth) acrylates such as 1,6-hexanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, triacryl formal, Bisphenoxyethanol full orange acrylate, dicyclopentanedienyl diacrylate, alkyl modified products thereof, alkyl ether modified products, alkyl ester modified products, and the like can be used. Two or more of these may be contained.

  Among these, from the viewpoints of solubility and patternability, a compound having a (meth) acryloyl group is preferable, and a polyfunctional compound having three or more (meth) acryloyl groups is preferable. By using a polyfunctional compound having three or more (meth) acryloyl groups, a sufficiently cured film can be formed. Moreover, the compound which has a carboxyl group is preferable from a viewpoint of improving alkali developability and heat resistance, and suppressing a color transfer more. A compound having three or more (meth) acryloyl groups and a carboxyl group is more preferable. Although it is not certain, since the radical polymerizable compound has three or more (meth) acryloyl groups, the reaction between the general formula (1) and the radical polymerizable compound proceeds sufficiently to increase the film density, Since the radically polymerizable compound has a carboxyl group, the film density is increased by a hydrogen bond between the nitrogen atom or carbonyl group contained in the compound represented by the general formula (1) and the carboxyl group contained in the radically polymerizable compound. This is presumed to be because the movement of the color material is suppressed by further increasing the space for the color material to pass through and decreasing. Examples of such a compound include penta (meth) acryloyloxydipentaerythritol monosuccinate.

  The content of the radical polymerizable compound is preferably 5% by mass or more and more preferably 10% by mass or more in the solid content excluding the color material of the color filter photosensitive composition from the viewpoint of patterning properties. On the other hand, from the viewpoint of suppressing film thickness unevenness during film formation and suppressing deformation of the pattern due to flow during firing, the content of the radical polymerizable compound is the solid content excluding the color material of the color filter photosensitive composition. In the inside, 70 mass% or less is preferable, and 60 mass% or less is more preferable.

  In addition, the total content of the compound represented by the general formula (1) and the radical polymerizable compound is 40% by mass or more in the solid content excluding the color material of the color filter photosensitive composition from the viewpoint of patternability. Preferably, 50 mass% or more is more preferable. On the other hand, the total content of the compound represented by the general formula (1) and the radical polymerizable compound is a color filter from the viewpoint of suppressing film thickness unevenness during film formation and suppressing deformation of the pattern due to flow during firing. 80 mass% or less is preferable in solid content except the coloring material of the photosensitive composition for light, and 70 mass% or less is more preferable.

  The photosensitive composition for a color filter according to the first aspect of the present invention further includes a binder resin, a color material, a photopolymerization initiator, a chain transfer agent, a sensitizer, an organic solvent, a polymerization inhibitor, an adhesion improver, and an interface. You may contain an activator, an organic acid, an organic amino compound, a hardening | curing agent, etc. Details of these components will be described later.

  The second aspect of the present invention will be described. The photosensitive composition for color filters of the second aspect of the present invention contains a compound represented by the following general formula (5) and a radically polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group. To do. By containing a compound represented by the following general formula (5), color transfer can be suppressed, and by containing a radically polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group. A pattern can be formed by an exposure / development process described later. Furthermore, since the film density can be further increased by thermal crosslinking in addition to photocrosslinking by combining such a radical polymerizable compound and a compound represented by the following general formula (5), In addition to suppressing color transfer, which is a phenomenon in which the color material in the pixel formed later penetrates, the color material in the pixel formed earlier exudes the color material that penetrates into the pixel formed later. Can also be suppressed. In addition, due to the interaction between the nitrogen atom contained in the condensed ring skeleton of the compound having the structure represented by the following general formula (5) and the carboxyl group contained in the radical polymerizable compound described later, the high density of the film by heating It is presumed that the process proceeds, and even a heat treatment at a low temperature of 150 ° C. or lower can be easily cured.

In the general formula (5), R ^{5 to} R ⁸ represent a hydrogen atom or a monovalent organic group represented by the following structural formula (3). However, at least one of R ^{5 to} R ⁸ represents a monovalent organic group represented by the following structural formula (3).

At least one of R ^{5 to} R ⁸ represents a monovalent organic group represented by the structural formula (3). When at least one is a monovalent organic group represented by the structural formula (3), it reacts with a carboxyl group or the like contained in a radical polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group. In addition, color migration and color material bleeding can be suppressed. Although it is not certain, densification of the film by the reaction of an epoxy group and a radical polymerizable compound having a carboxyl group contained in the compound represented by the general formula (5), or a compound represented by the general formula (5) The density of the film is increased by the interaction between the nitrogen atoms contained in the condensed ring skeleton and the carboxyl group contained in the radically polymerizable compound, thereby reducing the space for the color material to pass through, thereby moving the color material. Presumed to be suppressed. In addition, when the photosensitive composition for color filters of the second aspect of the present invention contains a binder resin having a carboxyl group, the monovalent organic group represented by the structural formula (3) and the binder resin The reaction with the carboxyl group of also occurs. From the viewpoint of further improving heat resistance and further suppressing color migration and color material bleeding, the monovalent organic group represented by the above structural formula (3) has two or more of R ^{5 to} R ^8. It is preferable to have three or more, more preferably four. A compound in which all of R ^{5 to} R ⁸ represent a monovalent organic group represented by the structural formula (3) is represented by the following structural formula (6).

In the general formula (5), R ^{5 to} R ⁸ may have a hydrogen atom together with the monovalent organic group represented by the structural formula (3).

  As a compound represented by General formula (5), the compound which has the following structures is mentioned, for example. Two or more of these may be contained.

  The content of the compound represented by the general formula (5) in the photosensitive composition for color filters of the present invention is a solid content excluding the color material of the photosensitive composition for color filters from the viewpoint of adhesion to the substrate. In the inside, 0.5 mass% or more is preferable, 1 mass% or more is more preferable, and 5 mass% or more is further more preferable. In addition, the content of the compound represented by the general formula (5) is 5% in the solid content excluding the color material of the photosensitive composition for a color filter, from the viewpoint of further suppressing the color transfer and the bleeding of the color material. % Or more is preferable, and 10 mass% or more is more preferable. On the other hand, the content of the compound represented by the general formula (5) is 25% by mass or less in the solid content excluding the color material of the photosensitive composition for a color filter, from the viewpoint of patterning properties and dissolution residue suppression during patterning. Is preferable, and 20 mass% or less is more preferable.

The compound represented by the general formula (1) and the compound represented by the general formula (5) contained in the photosensitive composition for a color filter can be prepared using various components such as preparative GPC, preparative HPLC, and column purification. The structure can be identified by conducting analysis by GC-MS, LC-MS, IR, ¹ H-NMR, ¹³ C-NMR, two-dimensional NMR such as HMBC and HMQC, etc. .

  The photosensitive composition for a color filter of the second aspect of the present invention contains a radically polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group. By having three or more (meth) acryloyl groups, a sufficiently cured film can be formed, and by having a carboxyl group, alkali developability and heat resistance can be improved and color migration can be further suppressed. it can. Although it is not certain, since the radical polymerizable compound has three or more (meth) acryloyl groups and a carboxyl group, the reaction with the compound represented by the general formula (5) sufficiently proceeds to increase the film density. In addition, the color material passes due to the densification of the film due to the interaction between the nitrogen atom contained in the condensed ring skeleton of the compound represented by the general formula (5) and the carboxyl group contained in the radical polymerizable compound. It is presumed that the movement of the coloring material is suppressed due to the decrease in the space. Examples of such a compound include penta (meth) acryloyloxydipentaerythritol monosuccinate.

  The content of the radically polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group in the photosensitive composition for a color filter of the present invention is sensitive to color filters from the viewpoint of further suppressing color transfer. 5 mass% or more is preferable in solid content except the coloring material of a composition, and 10 mass% or more is more preferable. On the other hand, three or more (meth) acryloyloxy groups and carboxyl groups in the photosensitive composition for a color filter are used from the viewpoint of suppressing film thickness unevenness during film formation and suppressing pattern deformation due to flow during firing. 70 mass% or less is preferable in solid content except the coloring material of the photosensitive composition for color filters, as for content of the radically polymerizable compound which has, 60 mass% or less is more preferable, and 50 mass% or less is further more preferable.

  The photosensitive composition for a color filter of the second aspect of the present invention contains another radical polymerizable compound in addition to a radical polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group. Also good. Examples of the radically polymerizable compound include those exemplified as the radically polymerizable compound in the color filter photosensitive composition of the first aspect.

  The total content of the radical polymerizable compound having three or more (meth) acryloyloxy groups and carboxyl groups and other radical polymerizable compounds excludes the color material of the photosensitive composition for color filters from the viewpoint of patterning properties. In solid content, 20 mass% or more is preferable and 30 mass% or more is more preferable. In addition, from the viewpoint of suppressing film thickness unevenness during film formation and suppressing deformation of the pattern due to flow during firing, radically polymerizable compounds having three or more (meth) acryloyloxy groups and carboxyl groups and other radicals 80 mass% or less is preferable in solid content except the coloring material of the photosensitive composition for color filters, and, as for the total content of a polymeric compound, 70 mass% or less is more preferable.

  The photosensitive composition for a color filter according to the second aspect of the present invention further includes a binder resin, a coloring material, a photopolymerization initiator, a chain transfer agent, a sensitizer, an organic solvent, a polymerization inhibitor, an adhesion improver, and an interface. You may contain an activator, an organic acid, an organic amino compound, a hardening | curing agent, etc.

  The photosensitive composition for a color filter of the present invention preferably contains a binder resin, can suppress film thickness unevenness during film formation, and can suppress deformation of a pattern due to flow during firing.

  Examples of the binder resin include acrylic resin, epoxy resin, polyimide resin, urethane resin, urea resin, polyvinyl alcohol resin, melamine resin, polyamide resin, polyamideimide resin, polyester resin, polyolefin resin, and the like. Two or more of these may be contained. From the viewpoint of stability, an acrylic resin is preferably used.

  As the acrylic resin, a copolymer of an unsaturated carboxylic acid and an ethylenically unsaturated compound is preferable.

  Examples of the unsaturated carboxylic acid include acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, vinyl acetic acid, and acid anhydrides thereof.

  Examples of the ethylenically unsaturated compound include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, ( Sec-butyl (meth) acrylate, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, benzyl (meth) acrylate, etc. Unsaturated carboxylic acid alkyl ester, styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, α-methylstyrene and other aromatic vinyl compounds, aminoethyl acrylate and other unsaturated carboxylic acid aminoalkyl esters, glycidyl Acrylate, glycidyl methacrylate, etc. Unsaturated carboxylic acid glycidyl esters, carboxylic acid vinyl esters such as vinyl acetate and vinyl propionate, vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and aliphatic conjugated dienes such as 1,3-butadiene and isoprene And macromonomers such as polystyrene, polymethyl acrylate, polymethyl methacrylate, polybutyl acrylate, polybutyl methacrylate, and polysilicone having a (meth) acryloyl group at the terminal.

  The acrylic resin preferably has an ethylenically unsaturated group in the side chain, and can improve sensitivity. Examples of the ethylenically unsaturated group include a vinyl group, an allyl group, an acrylic group, and a methacryl group. Examples of the acrylic resin having an ethylenically unsaturated group in the side chain include “Cyclomer” (registered trademark) P (Daicel Chemical Industries, Ltd.) and alkali-soluble cardo resin.

  The weight average molecular weight of the binder resin is preferably 3,000 or more and more preferably 9000 or more from the viewpoint of the strength of the cured film. On the other hand, the weight average molecular weight of the binder resin is preferably 200,000 or less and more preferably 100,000 or less from the viewpoint of the stability of the photosensitive composition for color filters. Here, the weight average molecular weight of the binder resin refers to a standard polystyrene equivalent value measured by gel permeation chromatography.

  The content of the binder resin is preferably 10% by mass or more, more preferably 20% by mass or more in the solid content excluding the color material of the photosensitive composition for color filter, from the viewpoint of suppressing film thickness unevenness during film formation. 30% by mass or more is more preferable. On the other hand, from the viewpoint of patterning property, the content of the binder resin is preferably 60% by mass or less, more preferably 50% by mass or less, and more preferably 40% by mass or less in the solid content excluding the color material of the photosensitive composition for color filter. Is more preferable.

  The photosensitive composition for a color filter of the present invention preferably contains a color material, and can form pixels such as red, green, blue, and yellow, a black matrix, and the like. Examples of the color material include pigments and dyes, and examples of the pigment include organic pigments and inorganic pigments. Two or more of these may be contained. Among these, in the case of the photosensitive composition for color filters used for a colored pixel, an organic pigment and a dye are preferable, and the light transmittance of the colored pixel can be improved.

  Examples of the red color material include C.I. I. Pigment Red (hereinafter “PR”) 9, PR48, PR97, PR122, PR123, PR144, PR149, PR166, PR168, PR177, PR179, PR180, PR192, PR209, PR215, PR216, PR217, PR220, PR223, PR224, PR226 , PR227, PR228, PR240, PR254, and the like. From the viewpoint of the luminance characteristics of the pixels, PR254 and PR177 are preferable.

  Examples of the green color material include C.I. I. Pigment Green (hereinafter “PG”) PG1, PG2, PG4, PG7, PG8, PG10, PG13, PG14, PG15, PG17, PG18, PG19, PG26, PG36, PG38, PG39, PG45, PG48, PG50, PG51, PG54 , PG55, PG58, and PG59. From the viewpoint of the luminance characteristics of the pixels, PG58 and PG59 are preferable.

  Examples of the yellow color material include C.I. I. Pigment Yellow (hereinafter referred to as “PY”) 12, PY13, PY17, PY20, PY24, PY83, PY86, PY93, PY95, PY109, PY110, PY117, PY125, PY129, PY137, PY138, PY139, PY147, PY148, PY150, PY148, PY3 , PY154, PY166, PY168, PY185, and the like. From the viewpoint of color purity, transmittance, and contrast ratio, PY129, PY138, PY139, and PY150 are preferable, PY138 and PY150 are more preferable, and PY150 is more preferable.

  Examples of the orange color material include C.I. I. Pigment orange (hereinafter “PO”) 13, PO31, PO36, PO38, PO40, PO42, PO43, PO51, PO55, PO59, PO61, PO64, PO65, PO71, and the like.

  Examples of the blue pigment include C.I. I. Pigment Blue (hereinafter “PB”) 15, PB15: 3, PB15: 4, PB15: 6, PB21, PB22, PB60, PB64 and the like.

  Examples of purple pigments include C.I. I. Pigment violet (hereinafter referred to as “PV”) 19, PV23, PV29, PV30, PV32, PV37, PV40, PV50, etc. (all numbers are color index No.).

  Examples of the dye include oil-soluble dyes, acid dyes, direct dyes, basic dyes, and acid mordant dyes. Further, the dye may be raked or a salt-forming compound of a dye and a nitrogen-containing compound.

  Examples of red, green, blue, purple, or yellow dyes include direct dyes, acid dyes, and basic dyes. Specific examples of these dyes include, for example, azo dyes, benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, xanthene dyes, cyanine dyes, squarylium dyes, croconium dyes, merocyanine dyes, stilbene dyes, Examples include diarylmethane dyes, triarylmethane dyes, fluorane dyes, spiropyran dyes, phthalocyanine dyes, indigo dyes, fulgide dyes, nickel complex dyes, and azulene dyes. The dye may be dissolved in the photosensitive composition or dispersed as particles.

  In order to increase resistance to heat, light, acid, alkali, organic solvent, etc., the basic dye is preferably a salt-forming compound comprising an organic acid such as organic sulfonic acid or organic carboxylic acid or perchloric acid. A salt-forming compound composed of naphthalenesulfonic acid such as acid or perchloric acid is more preferable. Similarly, in order to increase resistance to heat, light, acid, alkali or organic solvent, the acid dye and the direct dye may be a salt-forming compound composed of a quaternary ammonium salt, a primary to tertiary amine or a sulfonamide. preferable.

  In the case of the photosensitive composition for color filters used for the black matrix, a colorant having high light shielding properties is preferable. For example, organic pigments such as pigment black 7, carbon black, graphite, iron oxide, manganese oxide, titanium black Etc. are preferable.

  These color materials may be surface-treated. Examples of the surface treatment include rosin treatment, acidic group treatment, basic treatment and the like.

  From the viewpoint of improving the light transmittance of the colored pixels of the color filter substrate, a dye is preferable as the color material. On the other hand, dyes tend to transfer colors, and in particular, colored pixels containing xanthene-based dyes tend to have low light transmittance due to color transfer. Since the photosensitive composition for color filters of the present invention can suppress color transfer, it can be suitably used for a member adjacent to a colored pixel containing a dye, and is a member adjacent to a colored pixel containing a xanthene dye. Can be more suitably used.

  The content of the color material is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and further preferably 1% by mass or more in the solid content of the color filter photosensitive composition from the viewpoint of colorability. preferable. On the other hand, the content of the coloring material is preferably 35% by mass or less, and more preferably 30% by mass or less in the solid content of the photosensitive composition for a color filter from the viewpoint of patterning properties. When the color filter photosensitive composition of the present invention is used as a photospacer or overcoat layer material, the colorant content is preferably 5% by mass or less in the solid content of the color filter photosensitive composition, 3 mass% or less is more preferable, and 0.5 mass% or less is further more preferable.

  The color material contained in the photosensitive composition for a color filter of the present invention is obtained by mass spectrometry using laser Raman spectroscopy (Ar + laser (457.9 nm)), a MALDI mass spectrometer, or a time-of-flight secondary ion mass spectrometer. Can be identified.

  The content of the color material in the photosensitive composition for color filter can be quantified by mass spectrometry using a MALDI mass spectrometer or a time-of-flight secondary ion mass spectrometer. From the content of other components, the proportion (mass%) in the solid content of the photosensitive composition for color filter can be determined. In addition, when the blending ratio of the raw material of the color filter photosensitive composition is known, it accounts for the solid content in the color filter photosensitive composition from the blending amount of the color material and the blending amount of other components. The ratio (mass%) can be determined.

  The photosensitive composition for a color filter of the present invention may contain a dispersant such as a pigment derivative together with a color material. Examples of the dispersant include low molecular dispersants such as pigment intermediates and derivatives, and polymer dispersants. Examples of the pigment derivative include a modified alkylamine of a pigment skeleton, a carboxylic acid derivative, and a sulfonic acid derivative that contribute to appropriate wetting and stabilization of the pigment. A sulfonic acid derivative having a pigment skeleton having a remarkable effect on the stabilization of the fine pigment is preferred.

  As the polymer dispersant, for example, various polymers such as polyester, polyalkylamine, polyallylamine, polyimine, polyamide, polyurethane, polyacrylate, polyimide, polyamideimide, and the like, or copolymers thereof are used alone, or It can be used by mixing. Among these polymer dispersants, those having an amine value of 5 to 200 in terms of solid content and an acid value of 1 to 100 are preferable. Among these, a polymer dispersant having a basic group is preferable, and the storage stability of the pigment dispersion and the photosensitive composition can be improved. Examples of commercially available polymer dispersants having a basic group include “Solsperse” (registered trademark) (manufactured by Avisia), “EFKA” (registered trademark) (manufactured by Efka), and “Azisper” (registered trademark). ) (Manufactured by Ajinomoto Fine Techno Co., Ltd.), “BYK” (registered trademark) (manufactured by Big Chemie), among others, “Solspers” (registered trademark) 24000 (manufactured by Avicia), “EFKA” (registered trademark) 4300, 4330 (manufactured by Efka), 4340 (manufactured by Efka), “Ajisper” (registered trademark) PB821, PB822 (manufactured by Ajinomoto Fine Techno Co., Ltd.), “BYK” (registered trademark) 161-163, 2000, 2001 6919, 21116 (manufactured by Big Chemie).

  When the photosensitive composition for a color filter of the present invention contains a polymer dispersant and / or a binder resin, the total content thereof is a photosensitive material for a color filter from the viewpoint of suppressing film thickness unevenness during film formation. 10 mass% or more is preferable in solid content except the coloring material of an adhesive composition, 20 mass% or more is more preferable, and 30 mass% or more is further more preferable. On the other hand, from the viewpoint of patterning properties, the total content of the polymer dispersant and the binder resin is preferably 60% by mass or less, and preferably 50% by mass or less in the solid content excluding the color material of the photosensitive composition for color filter. More preferred is 40% by mass or less.

  The photosensitive composition for a color filter of the present invention preferably contains a photopolymerization initiator, and can improve sensitivity during patterning. Here, the photopolymerization initiator refers to a compound that decomposes and / or reacts with light (including ultraviolet rays or electron beams) to generate radicals. Examples of the photopolymerization initiator include oxime ester compounds, α-aminoacetophenone compounds, benzophenone compounds, acetophenone compounds, oxanthone compounds, imidazole compounds, benzothiazole compounds, benzoxazole compounds, and carbazole compounds. , Triazine compounds, phosphorus compounds, titanocene compounds, and the like.

  More specifically, for example, benzophenone, N, N′-tetraethyl-4,4′-diaminobenzophenone, 4-methoxy-4′-dimethylaminobenzophenone, 2,2-diethoxyacetophenone, benzoin, benzoin methyl ether, Benzoin isobutyl ether, benzyldimethyl ketal, α-hydroxyisobutylphenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propane 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone, 2- ( Dimethylamino) -2- [ 4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, t-butylanthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone 2-ethylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, 1,2-benzoanthraquinone, 1,4-dimethylanthraquinone, 2-phenylanthraquinone, 2- (o-chlorophenyl) -4, 5-diphenylimidazole dimer, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 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-dioxolanyl) methoxybenzoyl} -9H-carbazole- 3-yl]-, 1- (O-acetyloxime), 4- (p-methoxyphenyl) -2,6-di- (trichloromethyl) -s-triazine, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, 1,2-octanedione, 1- [4- (phenylthio) -2- (O-benzoyloxime)], “Adeka Arcles” (registered trademark) N-1919,) NCI-831, NCI-930 ADEKA), “IRGACURE” (trademark registration) 369, 379, OXE01, OXE02 (manufactured by Ciba Specialty Chemicals Co., Ltd.). Among these, because of high sensitivity, “Adeka Arcles” (registered trademark) N-1919, NCI-930, NCI-831 (manufactured by ADEKA Corporation), “IRGACURE” (registered trademark) OXE-02 ( Ciba Specialty Chemicals) is preferred.

  The content of the photopolymerization initiator is preferably 1% by mass or more, and more preferably 2% by mass or more in the solid content excluding the color material of the photosensitive composition for color filter, from the viewpoints of sensitivity, patternability, and processability. 5 mass% or more is more preferable. On the other hand, the content of the photopolymerization initiator is preferably 30% by mass or less and 20% by mass in the solid content excluding the color material of the color filter photosensitive composition from the viewpoints of sensitivity, patternability, processability, and heat resistance. % Or less is more preferable, and 15% by mass or less is more preferable.

  The photosensitive composition for a color filter of the present invention may contain a chain transfer agent in combination with a photopolymerization initiator, and can further improve sensitivity. Examples of the chain transfer agent include thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, and 2-mercaptonicotinic acid. 3- [N- (2-mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto 2-butanol, merca Tophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris (3-mercaptopropionate), 1,3,5-tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione), pentaerythritol tetrakis (3-mercaptopropionate), 1,4-bis (3-mercaptobutyryloxy) butane, “Karenz” (registered trademark) MT PE-1 (manufactured by Showa Denko KK), “Karenz” (registered trademark) MT NR-1 (manufactured by Showa Denko KK), Mercapto compounds such as “Karenz” (registered trademark) MT BD-1 (manufactured by Showa Denko KK), the mercapto Disulfide compounds obtained compound is oxidized, iodoacetic acid, iodopropionic acid, 2-iodo ethanol, 2-iodo-ethanesulfonic acid, iodinated alkyl compounds such as 3-iodo propane sulfonic acid.

  The photosensitive composition for a color filter of the present invention may further contain a sensitizer and can further improve sensitivity. Examples of the sensitizer include thioxanthone sensitizers, aromatic or aliphatic tertiary amines, and the like. Examples of the thioxanthone sensitizer include thioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthen-9-one, “KAYACURE” (registered trademark) DETX-S (manufactured by Nippon Kayaku Co., Ltd.), and the like. Can be mentioned.

  The photosensitive composition for color filters of the present invention may further contain an organic solvent. Examples of the organic solvent include diethylene glycol monobutyl ether acetate, benzyl acetate, ethyl benzoate, methyl benzoate, diethyl malonate, 2-ethylhexyl acetate, 2-butoxyethyl acetate, ethylene glycol monobutyl ether acetate, diethyl oxalate, ethyl acetoacetate, Cyclohexyl acetate, 3-methoxy-butyl acetate, methyl acetoacetate, ethyl-3-ethoxypropionate, 2-ethylbutyl acetate, isopentylpropionate, propylene glycol monomethyl ether propionate, pentyl acetate, propylene glycol monomethyl ether Acetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene Glycol monoethyl ether, diethylene glycol monomethyl ether, monoethyl ether, methyl carbitol, ethyl carbitol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol tertiary butyl ether, dipropylene glycol monomethyl ether, ethyl acetate, butyl acetate Isopentylbutanol acetate, 3-methyl-2-butanol, 3-methyl-3-methoxybutanol, cyclopentanone, cyclohexanone, xylene, ethylbenzene, solvent naphtha and the like. Two or more of these may be contained.

  The photosensitive composition for a color filter of the present invention may further contain a polymerization inhibitor, and can improve the stability. The polymerization inhibitor generally exhibits an action of inhibiting or stopping polymerization due to radicals generated by heat, light, radical initiators, etc., and generally prevents gelation of thermosetting resins or at the time of polymer production. Used to stop polymerization. Examples of the polymerization inhibitor include hydroquinone, tert-butylhydroquinone, 2,5-bis (1,1,3,3-tetramethylbutyl) hydroquinone, 2,5-bis (1,1-dimethylbutyl) hydroquinone, Catechol, tert-butylcatechol and the like can be mentioned. Two or more of these may be contained.

  The photosensitive composition for color filters of the present invention may further contain an adhesion improver, and can improve the adhesion of the coating film of the photosensitive composition for color filters to the substrate. Examples of the adhesion improving agent include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, and N- (2-amino). Ethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl Examples include silane coupling agents such as trimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane. Two or more of these may be contained.

  The photosensitive composition for a color filter of the present invention may further contain a surfactant, and can improve the coating property and the uniformity of the coating film surface of the photosensitive composition for a color filter. Examples of the surfactant include anionic surfactants such as ammonium lauryl sulfate and polyoxyethylene alkyl ether sulfate triethanolamine, cationic surfactants such as stearylamine acetate and lauryltrimethylammonium chloride, lauryldimethylamine oxide, and lauryl. Amphoteric surfactants such as carboxymethylhydroxyethyl imidazolium betaine, nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, sorbitan monostearate, fluorine-based surfactants and silicon-based surfactants Is mentioned. Two or more of these may be contained. It is preferable that content of surfactant is 0.001-10 mass% with respect to the whole quantity of the photosensitive composition for color filters from a viewpoint of the in-plane uniformity of a coating film.

  The photosensitive composition for a color filter of the present invention includes, for example, a compound having a structure represented by the general formula (1) or (5), a radical polymerizable compound, and, if necessary, a coloring material, a binder resin, and an organic solvent. The other components can be dispersed to prepare a pigment dispersion, and further blended with other components as necessary. Examples of the disperser include a sand mill, a ball mill, a bead mill, a three roll mill, and an attritor. Among these, a bead mill excellent in dispersion efficiency is preferable. Examples of the dispersed beads include zirconia beads, alumina beads, and glass beads. Among these, zirconia beads are preferable. When a pigment is contained as a colorant, it is preferable to add a solvent or the like to the pigment powder in advance and make secondary particles (particle diameter of about 1 to 50 μm) finer by a disperser.

  Next, the color filter substrate of the present invention will be described. The color filter substrate has pixels such as red and blue on the substrate. Further, it preferably has a black matrix, a photospacer, and an overcoat layer, and may have an alignment film, a polarizing plate, a retardation plate, an antireflection film, a transparent electrode, a diffusion plate, and the like. It is preferable to have a pixel, a black matrix, a photospacer and / or an overcoat layer comprising the photosensitive composition for a color filter of the present invention.

  Examples of the substrate include inorganic glass plates such as soda glass, alkali-free glass, borosilicate glass, quartz glass, aluminoborosilicate glass, aluminosilicate glass, alkali aluminosilicate glass, and soda lime glass whose surface is coated with silica. And organic plastic films and sheets. Two or more of these may be laminated.

  The organic plastic film or sheet may be a self-supporting film, or may be a film formed by coating or the like on a substrate such as a glass substrate. In the case of such a coating film, it can be peeled off by appropriately adjusting the adhesion between the substrate and the film with a laser or the like. Examples of the material of the organic plastic include polyester such as polypropylene, polyethylene, polystyrene, and polyethylene terephthalate (PET), polyphenylene sulfide (PPS), polyimide, polyamide, polyamideimide, polyethersulfone, polytetrafluoroethylene (PTFE), and the like. Fluorine-containing polymers, polyether ether ketone, polyphenylene ether, polyarylate, polysulfone and the like can be mentioned.

  From the viewpoint of the strength of the substrate, the substrate is preferably a film having a thickness of 5 μm or more, and more preferably 10 μm or more. On the other hand, from the viewpoint of flexibility, the substrate is preferably a film having a thickness of 100 μm or less.

  A black matrix may be formed on the substrate. Note that when the display device including the color filter substrate of the present invention is a reflective display device, the substrate may be opaque.

  Examples of the pixel include colored pixels such as red and blue and transparent pixels. As a material which comprises a pixel, the photosensitive composition for color filters of this invention, the coloring photosensitive composition containing binder resins, such as an acrylic resin and a polyimide resin, and a radically polymerizable compound, etc. are mentioned, for example. From the viewpoint of improving color purity, the film thickness of the pixel is preferably 0.5 μm or more, more preferably 1.0 μm or more, and more preferably 1.4 μm or more. On the other hand, from the viewpoint of improving the flatness, pattern processability and reliability of the color filter substrate, it is preferably 3.0 μm or less, and more preferably 2.8 μm or less.

  The black matrix prevents a decrease in contrast and color purity due to light leakage between pixels, and is preferably disposed between pixels or in a frame portion. As a material constituting the black matrix, for example, the photosensitive composition for a color filter of the present invention, a photosensitive composition containing a binder resin such as an acrylic resin or a polyimide resin and a radical polymerizable compound, or colored black. Examples include non-photosensitive resin compositions. The film thickness of the black matrix is preferably 0.5 μm or more and more preferably 1.0 μm or more from the viewpoint of light shielding properties. On the other hand, from the viewpoint of workability, it is preferably 2.0 μm or less, more preferably 1.5 μm or less.

  The photospacer provides a certain gap between the opposing substrates and can be filled with a liquid crystal compound or the like between the gaps, so that the step of arranging the spacer can be omitted when manufacturing the liquid crystal display device. it can. It is preferable that the liquid crystal display device is fixed at a specific place on the color filter substrate so as to be in contact with the counter substrate. As a material which comprises a photospacer, the photosensitive composition for color filters of this invention, the photosensitive composition containing binder resins, such as an acrylic resin and a polyimide resin, and a radically polymerizable compound, etc. are mentioned, for example. Examples of the shape of the photo spacer include a columnar shape, a prismatic shape, a truncated cone shape, and a truncated pyramid shape. The diameter of the photo spacer is not particularly specified, but is preferably 2 to 20 μm, and more preferably 3 to 10 μm. The height of the photospacer is preferably 1 to 10 μm.

  The overcoat layer suppresses the permeation of impurities from the pixels of the color filter substrate, or flattens the steps due to the pixels of the color filter substrate. As a material constituting the overcoat layer, for example, the photosensitive composition for a color filter of the present invention, an epoxy resin, an acrylic epoxy resin, an acrylic resin, a siloxane resin, a polyimide resin, or a photosensitive resin that is commercially available as a planarizing material. Or a non-photosensitive material etc. are mentioned. The film thickness of the overcoat layer is preferably 0.5 μm or more, more preferably 1.0 μm or more, from the viewpoint of workability. On the other hand, from the viewpoint of flatness of the color filter substrate, 5.0 μm or less is preferable, and 3.0 μm or less is more preferable.

  Examples of the material constituting the transparent electrode include metals such as aluminum, chromium, tantalum, titanium, neodymium, and molybdenum, Indium-Tin-Oxide (ITO), Indium-Zinc-Oxide (InZnO), and the like.

  Examples of the method for producing the color filter substrate include a method of patterning pixels made of a resin composition on the substrate. Since the photosensitive composition for a color filter of the present invention can suppress color migration, it can be suitably used for a member adjacent to a pixel that easily undergoes color migration. Below, a manufacturing method is demonstrated for the example of the color filter board | substrate which has a pixel which consists of the photosensitive composition for color filters of this invention. A color filter substrate can be obtained by applying the photosensitive composition for a color filter of the present invention on a substrate, patterning by selective exposure and development using a photomask, and baking to form pixels, thereby obtaining a color filter substrate. .

  Examples of the method for applying the photosensitive composition for a color filter on a substrate include a spin coater, a bar coater, a blade coater, a roll coater, a die coater, an ink jet printing method, a screen printing method, and a substrate for a color filter. Examples include a method of immersing in a photosensitive composition, a method of spraying a photosensitive composition for a color filter onto a substrate, and the like. Then, the coating film of the photosensitive composition for color filters is formed on a board | substrate by drying the board | substrate which apply | coated the photosensitive composition for color filters. Examples of the drying method include air drying, heat drying, and vacuum drying. Two or more of these may be combined. For example, it is preferable to dry under reduced pressure and then heat dry. The heating and drying temperature is preferably 80 to 130 ° C., and the hot drying apparatus is preferably a hot air oven or a hot plate. In the case of a color filter substrate having a black matrix, it is preferable to form a coating film of the color filter photosensitive composition on a substrate on which a black matrix has been formed in advance.

  Next, a photomask is disposed on the coating film of the color filter photosensitive composition, and selective exposure is performed. Examples of the exposure machine include a proximity exposure machine, a mirror projection exposure machine, a lens scan exposure machine, and a stepper. From the viewpoint of accuracy, a lens scanning exposure machine is preferable. Examples of the light source used for exposure include an ultrahigh pressure mercury lamp, a chemical lamp, and a high pressure mercury lamp.

  Thereafter, the unexposed portion is removed by development with an alkaline developer to form a coating film pattern. Examples of the alkaline substance used in the alkaline developer include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia, ethylamine, and n-propylamine. Examples include primary amines, secondary amines such as diethylamine and di-n-propylamine, tertiary amines such as triethylamine and methyldiethylamine, and organic alkalis such as tetramethylammonium hydroxide. Examples of the alkaline developer include 0.02 to 1% by mass of potassium hydroxide or tetramethylammonium hydroxide. Examples of the developing method include a method of immersing the exposed coating film in an alkali developer for 20 to 300 seconds.

  Thereafter, the obtained coating film pattern is heated to obtain a color filter substrate on which pixels are patterned. The heat treatment may be performed in any of air, nitrogen atmosphere, and vacuum. The heating temperature is preferably 80 to 350 ° C, more preferably 150 to 350 ° C, and further preferably 180 to 250 ° C. In the present invention, the nitrogen atom contained in the condensed skeleton of the compound having the structure represented by the general formula (1) or the compound having the structure represented by the general formula (5), and a radical polymerizable compound It is presumed that the density of the film proceeds due to the interaction with the contained carboxyl group. Therefore, it can be processed even on a substrate such as a film that is difficult to heat-treat at 150 ° C. or higher. The heating time is preferably 5 minutes to 5 hours. As the heat treatment apparatus, a hot air oven or a hot plate is preferable. The heat treatment may be performed continuously or stepwise.

  The pixels are sequentially formed by the above method for each of the 3 to 6 color pixels included in the color filter substrate. The order of forming each color is not particularly limited, but when forming a pixel containing a dye, it is preferable to form the pixel containing the dye after forming other pixels from the viewpoint of further suppressing the color transfer of the coloring material. In particular, a pixel containing a xanthene dye is preferably formed after formation of another pixel because the xanthene dye is likely to transfer color. Further, when the photosensitive composition for a color filter of the present invention contains a dye such as a xanthene-based dye, even if a pixel comprising the photosensitive composition for a color filter is formed first, the color transfer is caused. Can be suppressed.

  Although a color filter substrate having pixels made of the photosensitive composition for color filters of the present invention has been described as an example, a black matrix made of the photosensitive composition for color filters of the present invention can be formed in the same manner. In addition, the overcoat layer made of the color filter photosensitive composition of the present invention can be formed by applying the color filter photosensitive composition so as to cover the pixels, and similarly drying, exposing and heating. . Similarly, the photospacer comprising the photosensitive composition for color filter of the present invention is formed by coating on a substrate, drying, patterning by selective exposure and development using a photomask, and baking. be able to. The transparent electrode substrate can be formed by, for example, a sputtering method or a vacuum deposition method.

  The color filter substrate of the present invention can be used as a component of a display device such as a liquid crystal display, an organic EL display, or electronic paper. That is, the display device of the present invention includes the color filter substrate and the display element of the present invention. Further, the display device may include a light source such as an external light source, various films such as a brightness enhancement film and a diffusion plate. The display device refers to a device that displays an image by visually recognizing a part of the screen. Examples of the display element include a liquid crystal element, an organic EL element, an inorganic EL element, a display element using MEMS, a display element using quantum dots, electronic ink, an electronic powder fluid, and an electrophoretic element. Examples of the display device include a transmissive liquid crystal display, a transflective liquid crystal display, a reflective liquid crystal display, an organic EL display, an inorganic EL display, a quantum dot display, and electronic paper.

  As an example of a method for manufacturing a display device of the present invention, a method for manufacturing a liquid crystal display device is described below. The color filter substrate and the array substrate are bonded to each other through a liquid crystal alignment film provided on the substrates and a spacer for maintaining a cell gap. Note that a TFT liquid crystal display device or a TFD liquid crystal display device can be manufactured by providing a thin film transistor (TFT) element or a thin film diode (TFD) element, a scanning line, a signal line, or the like over an array substrate. Next, after injecting liquid crystal from the injection port provided in the seal portion, the injection port is sealed. Furthermore, a liquid crystal display device is completed by attaching a backlight and mounting an IC driver or the like. As the backlight, a two-wavelength LED, a three-wavelength LED, or a CCFL can be used, but a three-wavelength LED is preferable because the color reproduction range of the liquid crystal display device can be expanded and the power consumption can be kept low. .

  EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. First, the evaluation method in an Example and a comparative example is demonstrated.

<Residue>
The color filter photosensitive compositions obtained in Examples 1 to 12 and 15 and Comparative Examples 1 to 3, 5 and 7 were spin-coated on a 10 cm square glass substrate, dried at 90 ° C. for 10 minutes, A 1.7 μm coating film was obtained. The obtained coating film was immersed in a 0.3% by mass tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds, then washed with pure water, and visually confirmed for the presence of residues on the substrate. evaluated.
A: No residue on the substrate B: Residue on the edge of the substrate C: Residue on the substrate

<Color transfer resistance>
The photosensitive compositions for color filters obtained in Examples 1-8, 13, 15 and Comparative Examples 1-3, 7 were spin-coated on a glass substrate and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² , then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds, and washed with pure water. Firing was performed at 230 ° C. for 30 minutes to obtain a substrate on which a film having a thickness of 1.7 μm was formed. The photosensitive composition F1 obtained in Production Example 5 was spin-coated on the obtained substrate and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² through a photomask having a circular pattern with a diameter of 30 μm, and then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds. And washed with pure water to obtain a coated substrate having a circular hole with a thickness of 2 μm and a diameter of 30 μm. Luminance Y0 at the center of the circular hole was measured using a microspectrophotometer LCF-100MA manufactured by Otsuka Electronics Co., Ltd. Next, after the substrate with a film is baked at 230 ° C. for 30 minutes, the luminance Y1 at the center of the circular hole is measured, and Y1 / Y0 is calculated. The color transfer resistance, which is an index of the difficulty of the phenomenon of penetration of the coloring material inside, was evaluated. As the numerical value of Y1 / Y0 is closer to 1, color transfer is less likely to occur, which is preferable.

<Color material exudation resistance>
The color filter photosensitive compositions obtained in Examples 9 to 12 and Comparative Example 5 were spin-coated on a glass substrate and dried at 90 ° C. for 10 minutes. The resulting coating film was exposed to i-line 200 mJ / cm ² through a photomask having a circular pattern with a diameter of 30 μm, and then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds. And washed with pure water. Firing was performed at 230 ° C. for 30 minutes to obtain a coated substrate having a circular hole having a thickness of 1.7 μm and a diameter of 30 μm. Next, the photosensitive composition F3 obtained by the manufacture example 7 was apply | coated on the produced board | substrate with a film | membrane, and it dried for 10 minutes at 90 degreeC. The obtained coating film was exposed at i-line 200 mJ / cm ² and then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds. The substrate with a laminated film having a thickness of 2 μm made of the photosensitive composition F3 was obtained by washing with pure water. Luminance Y0 at the center of the circular hole was measured using a microspectrophotometer LCF-100MA manufactured by Otsuka Electronics Co., Ltd. Next, after baking the substrate with the laminated film at 230 ° C. for 30 minutes, the luminance Y1 at the center of the circular hole is measured, and Y1 / Y0 is calculated. The bleeding resistance of the color material, which is an index of the difficulty of generating a phenomenon that penetrates the formed pixels, was evaluated. As the numerical value of Y1 / Y0 is closer to 1, color transfer is less likely to occur, which is preferable.

<Adhesion (glass substrate)>
The photosensitive compositions for color filters obtained in Examples 5 to 8, 13, 15 and Comparative Example 1 were applied on a glass substrate and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² , then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds, and washed with pure water. The washed film was baked at 230 ° C. for 30 minutes to form a film having a thickness of 1.7 μm. After applying 10 straight scratches with a length of 1.5 cm at intervals of 1 mm to the obtained film using a single blade, the length was 1 with a single blade in the same manner so that the scratches would be perpendicular. Ten straight scratches with a length of 0.5 cm were attached at intervals of 1 mm to form a grid-like scratch. A 1.8 cm wide tape (manufactured by Sumitomo 3M Co., Ltd., trade name Scotch) is applied to the scratched portion of the grid pattern, and after standing for 1 minute, the tape is peeled off from the substrate, and then peeled off. The surface was observed with a microscope, and the adhesion to glass was evaluated according to the following evaluation criteria.
A: At least a part of the 1 mm square film remains on the grid. B: No 1 mm square film remains.

<Adhesion (BMS-1)>
Carbon powder (MA-8, manufactured by Mitsubishi Materials Corporation) 30 g, acrylic copolymer solution (“Cyclomer” (registered trademark) P ACA-250, manufactured by Daicel Chemical Industries, Ltd.) 20 g, and cyclohexanone 37 g were mixed. After dispersing for 1 hour with a homogenizer, 10 g of dipentaerythritol hexaacrylate and 3 g of a photopolymerization initiator “IRGACURE” (registered trademark) 369 (manufactured by Ciba Specialty Chemicals Co., Ltd.) are mixed and used for black matrix A composition (BM-1) was obtained.

A black matrix composition (BM-1) was spin-coated on a glass substrate and dried at 120 ° C. for 120 seconds. The obtained coating film was exposed at i-line 200 mJ / cm ² , then immersed in a 2.0 mass% sodium hydroxide aqueous solution for 2 minutes, washed with pure water, and baked in an oven at 230 ° C. for 30 minutes. A black matrix substrate (BMS-1) on which a 1.5 μm film was formed was obtained.

The photosensitive composition for a color filter obtained in Examples 5 to 8, 13, 15 and Comparative Example 1 was applied on a black matrix substrate (BMS-1) and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² , then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds, and washed with pure water. The washed film was baked at 230 ° C. for 30 minutes to form a film having a thickness of 1.7 μm. After applying 10 straight scratches with a length of 1.5 cm at intervals of 1 mm to the obtained film using a single blade, the length was 1 with a single blade in the same manner so that the scratches would be perpendicular. Ten straight scratches with a length of 0.5 cm were attached at intervals of 1 mm to form a grid-like scratch. A 1.8 cm wide tape (manufactured by Sumitomo 3M Co., Ltd., trade name Scotch) is applied to the scratched portion of the grid pattern, and after standing for 1 minute, the tape is peeled off from the substrate, and then peeled off. The surface was observed with a microscope, and the adhesion to the black matrix substrate (BMS-1) was evaluated according to the following criteria.
A: At least a part of the 1 mm square film remains on the grid. B: No 1 mm square film remains.

Production Example 1 (Preparation of dispersion (A1))
C. I. Pigment Red 254 150 g, “BYK” (registered trademark) 6919 (manufactured by Big Chemie, polymer dispersant) 75 g, “Cyclomer” (registered trademark) ACA250 (manufactured by Daicel Chemical Industries, Ltd., 45 mass% dipropylene glycol monomethyl ether solution) ) 100 g and propylene glycol monomethyl ether (PMA) 675 g were mixed to prepare a slurry. The beaker containing the slurry is connected with a dyno mill and a tube, and zirconia beads having a diameter of 0.5 mm are used as media, and dispersion treatment is performed for 8 hours at a peripheral speed of 14 m / s to prepare Pigment Red 254 dispersion (A1). did.

Production Example 2 (Preparation of Dispersion (A2))
C. I. Pigment Red 254 instead of C.I. I. Pigment Yellow 150 Dispersion (A2) was prepared in the same manner as in Production Example 1 except that 150 g of Pigment Yellow 150 was used.

Production Example 3 (Preparation of dispersion (A3))
In a three-necked flask, 15 g of Acid Red 289, 150 g of chloroform, and 8.9 g of N, N-dimethylformamide were added. Thereafter, the mixture was cooled to 20 ° C. or lower, and 10.9 g of thionyl chloride was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C. and stirred for 5 hours, then cooled to 20 ° C., a mixture of 12.5 g of 2-ethylhexylamine and 22.1 g of triethylamine was added, and the mixture was stirred for 5 hours at 20 ° C. A mixture was obtained. The solvent was distilled off from the obtained reaction mixture by a rotary evaporator and purified to obtain 10 g of a xanthene dye.

  The resulting xanthene dye 10 g, PB15: 90 g, “BYK” (registered trademark) 6919 67 g, “Cyclomer” ACA250 67 g, and PMA 766 g were mixed to prepare a slurry. The beaker containing the slurry is connected with a dyno mill and a tube, and the dispersion is performed for 8 hours at a peripheral speed of 10 m / s using zirconia beads having a diameter of 0.3 mm as a medium. Was prepared.

Production Example 4 (Synthesis of binder resin solution (B1))
In a 500 mL three-necked flask, 33 g (0.3 mol) of methyl methacrylate, 33 g (0.3 mol) of styrene, 34 g (0.4 mol) of methacrylic acid, 3 g of 2,2′-azobis (2-methylbutyronitrile) (0 0.02 mol) and 150 g of propylene glycol monomethyl ether acetate (PGMEA) were stirred, stirred at 90 ° C. for 2 hours, then the internal temperature was raised to 100 ° C., and further stirred for 1 hour to obtain a reaction solution. To the obtained reaction solution, 33 g (0.2 mol) of glycidyl methacrylate, 1,2 g (0.009 mol) of dimethylbenzylamine and 0.2 g (0.002 mol) of p-methoxyphenol were added at 90 ° C. After stirring for a period of time, 50 g of PGMEA was added to obtain a binder resin solution (B1) having a solid concentration of 40% by mass. When the acid value of the binder resin was measured with respect to a 0.1 mol / L potassium hydroxide / ethanol solution using a potentiometer automatic measurement device AT-610 manufactured by Kyoto Electronics Industry Co., Ltd., the acid value was 80.0 mg / mg. KOH / g). Moreover, when the weight average molecular weight of polystyrene conversion was computed using the GPC apparatus, the weight average molecular weight was 22000.

Production Example 5 (Preparation of photosensitive composition (F1))
In a 200 mL plastic bottle, 19.8 g of dispersion A3 obtained in Production Example 3, 23.16 g of binder resin solution B1 obtained in Production Example 4, “Kayarad” (registered trademark) DPHA (manufactured by Nippon Kayaku Co., Ltd.) , Polyfunctional radical polymerizable compound) 23.50 g, “ADEKA ARKLES” (registered trademark) N-1919 (manufactured by ADEKA, oxime ester photopolymerization initiator) 0.31 g, dipropylene glycol methyl ether acetate ( DPMA) 60.00 g was added and stirred for 3 hours to prepare a photosensitive composition (F1).

Production Example 6 (Preparation of photosensitive composition (F2))
Further, a photosensitive composition (F2) was prepared in the same manner as in Production Example 5 except that 0.18 g of “Emulgen” (registered trademark) 408 (manufactured by Kao Corporation, nonionic surfactant, HLB10) was added. did.

Production Example 7 (Preparation of photosensitive composition (F3))
In a 50 mL plastic bottle, 3.20 g of dispersion A1 obtained in Production Example 1, 1.37 g of dispersion A2 obtained in Production Example 2, 3.00 g of binder resin solution B1 obtained in Production Example 4, “Kayalad “(Registered trademark) DPHA 2.62 g,“ ADEKA ARKLES ”(registered trademark) N-1919 0.22 g, DPMA 24.75 g were added, and stirred for 3 hours to prepare a photosensitive composition (F3).

Example 1
In a 50 mL plastic bottle, 3.20 g of dispersion A1 obtained in Production Example 1, 1.37 g of dispersion A2 obtained in Production Example 2, 3.00 g of binder resin solution B1 obtained in Production Example 4, and a general formula 2.10 g of TA-G (compound represented by structural formula (4), manufactured by Shikoku Kasei Kogyo Co., Ltd.) as the compound represented by (1), penta (meth) acryloyloxydipentaerythritol as the radical polymerizable compound Monosuccinic acid ester (C1) 0.52 g, “Adeka Arcles” (registered trademark) N-1919 0.22 g, and DPMA 24.75 g as a photopolymerization initiator were added, and stirred for 3 hours, and photosensitized for color filters. Sex composition (E1) was prepared.

  About the obtained photosensitive composition for color filters, when the said method evaluated, the residue was not recognized on a board | substrate and Y1 / Y0 was 0.945.

Examples 2-4
Example 1 except that the dispersion and binder resin solution, the compound represented by the general formula (1), the radical polymerizable compound, the photopolymerization initiator, and the type and amount of the organic solvent were changed as shown in Table 1. In the same manner as above, photosensitive compositions for color filters (E2 to E4) were obtained. However, in Example 4, pentaerythritol triacrylate was used as the radical polymerizable compound C2. The obtained photosensitive composition for a color filter was used and evaluated by the above method.

Example 5
In a 50 mL plastic bottle, 3.20 g of dispersion A1 obtained in Production Example 1, 1.37 g of dispersion A2 obtained in Production Example 2, 3.00 g of binder resin solution B1 obtained in Production Example 4, radical polymerization 1.31 g of C1 as a functional compound, 1.31 g of TG-G (compound represented by Structural Formula (6), manufactured by Shikoku Kasei Kogyo Co., Ltd.) as a compound represented by the general formula (5), a photopolymerization initiator “Adeka Arcles” (registered trademark) N-1919 0.22 g and DPMA 24.75 g were added and stirred for 3 hours to prepare a photosensitive composition (E6) for a color filter.

  When the obtained photosensitive composition E6 for color filters was evaluated by the above method, a residue was observed on the substrate, but Y1 / Y0 was 0.991. Moreover, when the adhesiveness with a glass substrate and a black matrix substrate (BMS-1) was evaluated, a 1 mm square film remained on the substrate.

Examples 6-8, Comparative Examples 1-3
Except that the dispersion liquid, the binder resin solution, the radical polymerizable compound, the compound represented by the general formula (5), the epoxy compound, the photopolymerization initiator, and the type and amount of the organic solvent were changed as shown in Table 1. In the same manner as in Example 5, photosensitive compositions for color filters (E7 to E11) were obtained. However, in Example 8, pentaerythritol triacrylate was used as the radical polymerizable compound C2, and in Comparative Examples 2 to 3, "jER" (registered trademark) 834 (manufactured by Mitsubishi Chemical Corporation) was used as the epoxy compound. It was. Using the obtained photosensitive composition for a color filter, it was evaluated by the method described above.

  The composition of each Example and Comparative Example is shown in Table 1, the compound represented by the general formula (1) in the solid content excluding the color material, the radical polymerizable compound, the compound represented by the general formula (5), and the epoxy compound Table 2 summarizes the mass ratios of these and Table 3 summarizes the evaluation results.

Comparative Example 4
The color filter photosensitive composition E5 was spin-coated on a glass substrate and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² , then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds, and washed with pure water. Firing was performed at 230 ° C. for 30 minutes to obtain a substrate on which a film having a thickness of 1.7 μm was formed. The photosensitive composition F2 obtained in Production Example 6 was spin-coated on the obtained substrate and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² through a photomask having a circular pattern with a diameter of 30 μm, and then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds. And washed with pure water to obtain a coated substrate having a circular hole with a thickness of 2 μm and a diameter of 30 μm. Luminance Y0 at the center of the circular hole was measured using a microspectrophotometer LCF-100MA manufactured by Otsuka Electronics Co., Ltd. Subsequently, after baking the board | substrate with a film | membrane for 30 minutes at 230 degreeC, the brightness | luminance Y1 of the center part of a circular hole was measured, and it was 0.931 when Y1 / Y0 was computed.

Example 9
In a 50 mL plastic bottle, 5.00 g of dispersion A3 obtained in Production Example 3, 3.80 g of binder resin solution B1 obtained in Production Example 4, 1.65 g of C1 as a radical polymerizable compound, and General Formula (5) 1.65 g of TG-G as a compound represented, 0.27 g of “Adeka Arcles” (registered trademark) N-1919 and 29.31 g of DPMA as a photopolymerization initiator, and stirred for 3 hours, and photosensitivity for color filter Sex composition (E12) was prepared.

  When the obtained photosensitive composition E12 for color filters was evaluated by the above method, a slight residue was observed at the edge portion on the substrate. Further, when the bleeding resistance of the color material was evaluated by the above method, Y1 / Y0 was 1.000.

Examples 10-12, Comparative Example 5
Example 9 except that the dispersion and binder resin solution, radical polymerizable compound, compound represented by general formula (5), photopolymerization initiator, organic solvent and the amount of the organic solvent were changed as shown in Table 4. In the same manner as above, photosensitive compositions for color filters (E13 to E16) were obtained. The obtained photosensitive composition for a color filter was used and evaluated by the above method.

  The composition of each example and comparative example is shown in Table 4, the radically polymerizable compound in the solid content excluding the coloring material, the mass ratio of the compound represented by the general formula (5) in Table 5, and the evaluation results in Table 6. To summarize.

Example 13
Using the color filter photosensitive composition (E6) obtained in Example 5, the firing conditions of the color filter photosensitive composition (E6) coating film were changed from 230 ° C. for 30 minutes to 100 ° C. for 60 minutes. Except for the above, color transfer resistance, adhesion (glass substrate) and adhesion (BMS-1) were evaluated in the same manner as in Example 5. Y1 / Y0 was 0.975, and a 1 mm square film remained on the glass substrate and the black matrix substrate.

Example 14
Photosensitive film for color filter obtained in Example 5 on the film side of a laminated substrate in which a PET film “Therapy” (registered trademark) HP2 (U) (manufactured by Toray Film Processing Co., Ltd.) having a thickness of 38 μm was fixed to a glass substrate. The composition (E6) was spin-coated and dried at 90 ° C. for 10 minutes. The obtained coating film was exposed to i-line 200 mJ / cm ² , then shower-developed with a 0.3 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 50 seconds, and washed with pure water. Firing was performed at 100 ° C. for 60 minutes to obtain a substrate having a film having a thickness of 1.7 μm. When the PET film “Therapy HP2 (U)” (registered trademark) was observed, no shrinkage or deflection was observed.

Example 15
In a 50 mL plastic bottle, 5.65 g of binder resin solution B1 obtained in Production Example 4, 3.05 g of C1 as a radical polymerizable compound, and TG-G (Shikoku Chemical Industry Co., Ltd.) as a compound represented by the general formula (5) ), A compound represented by the structural formula (6)) 0.34 g, “Adeka Arcles” (registered trademark) N-1919 0.28 g and DPMA 23.63 g as a photopolymerization initiator were added and stirred for 3 hours. Thus, a photosensitive composition for color filters (E17) was prepared. When the obtained photosensitive composition for color filters (E17) was evaluated by the above method, no residue was found on the substrate, and Y1 / Y0 was 0.978. Moreover, when the adhesiveness with a glass substrate and a black matrix substrate (BMS-1) was evaluated, a 1 mm square film remained on the substrate.

Comparative Example 6
In a 50 mL plastic bottle, 3.20 g of dispersion A1 obtained in Production Example 1, 1.37 g of dispersion A2 obtained in Production Example 2, 3.00 g of binder resin solution B1 obtained in Production Example 4, radical polymerization C1 1.31 g, isocyanuric acid triglycidyl 1.31 g, “Adeka Arcles” (registered trademark) N-1919 0.22 g and DPMA 24.75 g were added as a photopolymerization initiator and stirred for 3 hours. Insoluble matter was generated and could not be used as a photosensitive composition for color filters.

Comparative Example 7
In a 50 mL plastic bottle, 3.20 g of dispersion A1 obtained in Production Example 1, 1.37 g of dispersion A2 obtained in Production Example 2, 3.00 g of binder resin solution B1 obtained in Production Example 4, radical polymerization 2.36 g of C2 as a functional compound, 0.26 g of TG-G (manufactured by Shikoku Kasei Kogyo Co., Ltd., compound represented by structural formula (6)) as a compound represented by the general formula (5), photopolymerization initiator “Adeka Arcles” (registered trademark) N-1919 0.22 g and DPMA 24.75 g were added and stirred for 3 hours to prepare a photosensitive composition for a color filter. About the obtained photosensitive composition for color filters, when the said method evaluated, the residue was not recognized on a board | substrate and Y1 / Y0 was 0.934.

  The photosensitive composition for a color filter of the present invention can be suitably used for a color filter substrate and a display device.

Claims (22)

Photosensitive composition for color filters containing a radically polymerizable compound and a compound represented by the following general formula (1).

(In the general formula (1), R ^{1 to} R ⁴ represent a hydrogen atom or a monovalent organic group represented by the following structural formula (2) or the following structural formula (3). However, R ^{1 to} R ⁴ At least one of them represents a monovalent organic group represented by the following structural formula (2).)

2. The photosensitive composition for a color filter according to claim 1, wherein at least two of R ^{1 to} R ^{4 in} the general formula (1) are monovalent organic groups represented by the structural formula (2). The photosensitive composition for color filters according to claim 1 or 2, wherein the compound represented by the general formula (1) has a structure represented by the following structural formula (4).

The photosensitive composition for color filters according to any one of claims 1 to 3, wherein the radical polymerizable compound contains a radical polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group. The photosensitive composition for color filters according to any one of claims 1 to 4, wherein the radically polymerizable compound contains penta (meth) acryloyloxydipentaerythritol monosuccinate. A photosensitive composition for a color filter comprising a radically polymerizable compound having three or more (meth) acryloyloxy groups and a carboxyl group, and a compound represented by the following general formula (5).

(In the general formula (5), R ^{5 to} R ⁸ represent a hydrogen atom or a monovalent organic group represented by the following structural formula (3). However, at least one of R ^{5 to} R ⁸ is the following: A monovalent organic group represented by Structural Formula (3) is shown.)

The photosensitive composition for a color filter according to claim 6, wherein in the general formula (5), at least three of R ^{5 to} R ⁸ are monovalent organic groups represented by the structural formula (3). The photosensitive composition for a color filter according to claim 6 or 7, wherein the radical polymerizable compound contains penta (meth) acryloyloxydipentaerythritol monosuccinate. The photosensitive composition for color filters according to any one of claims 6 to 8, wherein the compound represented by the general formula (5) has a structure represented by the following structural formula (6).

Furthermore, the photosensitive composition for color filters in any one of Claims 1-9 containing a coloring material. The photosensitive composition for a color filter according to claim 10, wherein the colorant contains a xanthene dye. The content of the radically polymerizable compound having the three or more (meth) acryloyloxy groups and a carboxyl group is 5% by mass or more and 70% by mass or less in a solid content excluding a coloring material. The photosensitive composition for color filters as described in any one of. The content of the compound represented by the general formula (1) is 5% by mass or more and 40% by mass or less in the solid content excluding the coloring material, or the content of the compound represented by the general formula (5) is It is 5 to 20 mass% in solid content except a color material, The photosensitive composition for color filters in any one of Claims 1-12. A color filter substrate comprising, in this order, a step of forming a pixel on the substrate using the photosensitive composition for a color filter according to claim 1, and a step of forming a pixel adjacent to the formed pixel. Production method. The method for producing a color filter substrate according to claim 14, wherein the adjacent pixels are formed using a photosensitive composition containing a xanthene dye. The method for producing a color filter substrate according to claim 14, wherein the photosensitive composition for a color filter contains a xanthene dye. The color filter substrate which has a pixel which consists of a photosensitive composition for color filters in any one of Claims 1-13 on a board | substrate. A color filter substrate having an overcoat layer made of the photosensitive composition for a color filter according to claim 1 on a substrate. The color filter board | substrate which has a photo spacer which consists of a photosensitive composition for color filters in any one of Claims 1-13 on a board | substrate. The color filter substrate which has a black matrix which consists of a photosensitive composition for color filters in any one of Claims 1-13 on a board | substrate. The color filter substrate according to claim 17, wherein the substrate is a film having a thickness of 5 μm to 100 μm. A display device using the color filter substrate according to claim 17.