TW202328237A - Photosensitive colored resin composition, color filter and display device - Google Patents

Abstract

A photosensitive colored resin composition comprising a color material, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator and a solvent, wherein the color material contains a diketopyrrolopyrrole-based pigment, C.I. Pigment Red 202 and C.I. Pigment Red 122.

Description

Photosensitive colored resin composition, color filter and display device

The invention relates to a photosensitive colored resin composition, a color filter and a display device.

In recent years, with the development of personal computers, especially portable personal computers, the demand for liquid crystal displays is increasing. The penetration rate of mobile displays (mobile phones, smart phones, tablet PCs (Personal Computers, personal computers)) is also increasing, and the market for liquid crystal displays is expanding day by day. Organic light-emitting display devices, such as organic EL (Electroluminescence, electroluminescence) displays with high visibility due to self-luminescence, are also attracting attention as next-generation image display devices. Color filters are used in these liquid crystal display devices or organic light emitting display devices. For example, the formation of a color image in a liquid crystal display device means that the light passing through the color filter is directly colored into the color of each pixel constituting the color filter, and the light of these colors is synthesized to form a color image. As a light source at this time, besides the conventional cold cathode tube, an organic light-emitting element or an inorganic light-emitting element that emits white light may be used. As for the organic light emitting display device, a color filter is used for color adjustment and the like.

Here, the color filter generally has: a substrate; a coloring layer formed on the substrate and including coloring patterns of three primary colors of red, green, and blue; and a light-shielding portion formed on the substrate to divide each coloring pattern. As a method of forming a colored layer in a color filter, for example, it is formed as follows: adding an alkali-soluble resin, a photopolymerizable compound, and a photoinitiator to a color material dispersion obtained by dispersing the color material with a dispersant or the like, To form a colored resin composition, apply the colored resin composition on a glass substrate and dry it, expose it using a photomask, and develop it to form a colored pattern, and fix the pattern by heating to form a colored pattern. layer. These steps are repeated for each color, thereby forming a color filter.

In the red coloring layer of the color filter, the coloring material has been conventionally used, for example, to adjust C.I. Pigment Red 177 (hereinafter, sometimes called R177) to a diketopyrrolopyrrole pigment (hereinafter, sometimes called DPP). use. However, since R177 whose transmittance is lower than that of DPP is toned into DPP, the higher the addition rate of R177, the less the transmittance of DPP can be fully utilized, and the brightness tends to be impaired.

For example, in Patent Document 1, the subject is to obtain a high tinting strength, high brightness, and excellent stability when preparing a pigment-dispersed resist composition for color filters based on a pigment-dispersed composition for color filters, thereby preventing A pigment-dispersed resist composition for a color filter that migrates to other colors such as adjacent green (Green), thereby proposing a pigment-dispersed composition for a color filter (which does not contain Pigment Red 122), which contains C.I. Diketopyrrolopyrrole pigments other than Pigment Red 264, quinacridone pigments other than C.I. Pigment Red 209 and C.I. Pigment Violet 19, pigment dispersants, alkali-soluble resins, and organic solvents.

In addition, in Patent Document 2, in order to solve problems such as low contrast ratio, low transmittance, dispersion stability/heat resistance or solvent resistance, and foreign substances deposited on the coating film when using quinacridone-based pigments, it is proposed A coloring composition for a color filter, which contains a quinacridone pigment, a pigment derivative, a specific alkaline dispersant, and a binder resin. [Prior Art Literature] [Patent Document]

Patent Document 1: Japanese Patent No. 6732080 Patent Document 2: Japanese Patent Laid-Open No. 2019-109487

[Problem to be solved by the invention]

In recent years, higher brightness has been demanded due to higher pigment concentration due to wider color gamut of color filters, or miniaturization of patterns and reduction of aperture area associated with higher resolution. When C.I. Pigment Red 202 (hereinafter, sometimes referred to as R202), which has a bluer hue, is used in combination with diketopyrrolopyrrole pigments instead of R177, the content ratio of diketopyrrolopyrrole pigments can be increased, and the brightness. On the other hand, as a problem specific to a liquid crystal display device, there is a problem of viewing angle dependence due to the refractive index anisotropy of a liquid crystal cell or a polarizing plate. The problem of this viewing angle dependence is a problem that the color tone or contrast of a recognized image changes when the liquid crystal display device is viewed from the front and when it is viewed from an oblique direction. With the increase in screen size of liquid crystal display devices in recent years, the importance of this problem of viewing angle characteristics has further increased. In order to improve the viewing angle dependence problem, a method of assembling a retardation film into a liquid crystal display device has been widely used in the past. However, the color filter used in the liquid crystal display device has a different phase difference due to the coloring pattern of each color of the coloring layer. Therefore, in the case of using the above-mentioned retardation film, it is impossible to adjust the phase difference of the coloring pattern of each color. However, it is difficult to completely solve the problem of viewing angle dependence. In particular, R202 not only has high crystallinity due to π-π interactions and intermolecular interactions, but also adopts a β-type crystal structure, so the coloring layer formed by combining diketopyrrolopyrrole pigments with R202 has a relatively low phase difference. high problem.

This invention is made|formed in view of the above-mentioned actual situation, and it aims at providing the photosensitive coloring resin composition which can form the colored layer which has high luminance and the retardation was reduced. Moreover, the object of this invention is to provide the color filter and display apparatus formed using this photosensitive colored resin composition. [Technical means to solve the problem]

The photosensitive colored resin composition of the present invention is characterized in that it contains a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, and a solvent, and The above color materials include diketopyrrolopyrrole pigments, C.I. Pigment Red 202, and C.I. Pigment Red 122.

The color filter of the present invention includes at least a substrate and a colored layer provided on the substrate, and at least one of the colored layers is a cured product of the photosensitive colored resin composition of the present invention. Also, the present invention provides a display device having the above-mentioned color filter of the present invention. [Effect of Invention]

According to the present invention, it is possible to provide a photosensitive colored resin composition capable of forming a colored layer having high brightness and reduced retardation. Also, according to the present invention, a color filter and a display device formed using the photosensitive colored resin composition can be provided.

Hereinafter, the photosensitive colored resin composition, color filter, and display device of the present invention will be described in detail in order. Furthermore, in the present invention, light includes electromagnetic waves of wavelengths in visible and invisible regions, and radiation, and radiation includes, for example, microwaves and electron beams. Specifically, it refers to electromagnetic waves and electron beams with a wavelength of 5 μm or less. In the present invention, (meth)acryl means each of acryl and methacryl, (meth)acryl means each of acrylic acid and methacryl, and (meth)acrylate means acrylate and methacryl. Acrylic each. In addition, in this specification, "~" which shows a numerical range is used in the meaning which includes the numerical value described before and after it as a lower limit and an upper limit.

I. Photosensitive colored resin composition The photosensitive colored resin composition of the present invention contains a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, and a solvent, and The above color materials include diketopyrrolopyrrole pigments, C.I. Pigment Red 202, and C.I. Pigment Red 122.

The photosensitive colored resin composition of the present invention can form high brightness by including diketopyrrolopyrrole pigment (DPP), C.I. Pigment Red 202 (R202), and C.I. Pigment Red 122 (R122) in the above coloring material A colored layer with reduced retardation. If DPP is combined with R202, which has a light blue hue, instead of R177, the content ratio of DPP can be increased, and the brightness can be improved. As mentioned above, R202 not only has high crystallinity due to π-π interaction and intermolecular interaction, but also has a β-type crystal structure, so the coloring layer formed by combining DPP and R202 has the problem of high retardation. On the other hand, in the present invention, R122 is further combined with DPP and R202. Here, R202 and R122 respectively have the following structures.

[chemical 1]

By using R202 and R122 together, the crystallization of R202 can be suppressed by the steric repulsion of the substituent _-CH3 of R122, and the crystallinity can be reduced, so a colored layer with a reduced phase difference can be formed. Even if a small amount of R122 is added, it has the effect of reducing the phase difference, so that the high brightness obtained by the combination of DPP and R202 can be maintained, and the phase difference can be reduced.

The photosensitive colored resin composition of the present invention contains a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, and a solvent, and may further contain other components within the range that does not impair the effect of the present invention. Hereinafter, each component of the photosensitive colored resin composition of this invention is demonstrated in detail sequentially.

[Color] In the present invention, the coloring material includes a diketopyrrolopyrrole pigment, C.I. Pigment Red 202, and C.I. Pigment Red 122. What is represented by following general formula (i) is mentioned as said diketopyrrolopyrrole pigment.

[Chem. 2] General formula (i) (In the general formula (i), ^A1 and ^A2 independently represent a halogen atom, methyl, ethyl, tert-butyl, phenyl, N,N-dimethylamino, trifluoromethyl, or cyanide base, k and k' each independently represent an integer of 0 to 5, and when k and k' are integers of 2 or more, the plurality of ^A1 and ^A2 may be the same or different)

As a specific example of a diketopyrrolopyrrole pigment, CI pigment red 254, 255, 264, 272, 291 is mentioned, for example. Among them, k and k' are 1, and A ¹ and A ² are each independently 4 in the diketopyrrolopyrrole pigment represented by the above-mentioned general formula (i) in terms of high brightness. - Chlorine or 4-bromo diketopyrrolopyrrole pigments, specifically, CI Pigment Red 254, 291 may be mentioned. In particular, it may be a diketopyrrolopyrrole pigment represented by the above general formula (i) in which k and k' are 1, and ^A1 and ^A2 are each a 4-bromo group, which may be a CI pigment Red 291.

The diketopyrrolopyrrole pigment may be used alone or in combination of two or more. The content ratio of the diketopyrrolopyrrole pigment is preferably, for example, 50% by mass to 97% by mass, relative to the total amount of the colorant, in terms of being able to form a colored layer with high brightness and reduced retardation. More preferably, it exists in the range of 60 mass % - 96 mass %.

The total content ratio of C.I. Pigment Red 202 and C.I. Pigment Red 122 is preferably 3% by mass to 50% by mass, for example, in terms of forming a colored layer with high brightness and reduced retardation relative to the total amount of coloring materials. % by mass, more preferably within the range of 4% by mass to 40% by mass. With respect to the total content of the above-mentioned C.I. Pigment Red 202 and C.I. Pigment Red 122, the content ratio of C.I. Pigment Red 122 can be, for example, 0.0001% by mass to 3% by mass in order to form a colored layer with high brightness and reduced phase difference. %, preferably in the range of 0.001% by mass to 3% by mass, more preferably in the range of 0.01% by mass to 3% by mass.

Regarding the total content ratio of the diketopyrrolopyrrole pigment, C.I. Pigment Red 202, and C.I. Pigment Red 122, with respect to the total amount of coloring materials, it is possible to form a colored layer with high brightness and reduced retardation, for example. It is 90 mass % or more, Preferably it is 95 mass % or more, More preferably, it is 98 mass % or more, It may be 100 mass %.

In the coloring material, other coloring materials different from the diketopyrrolopyrrole pigment, C.I. Pigment Red 202, and C.I. Pigment Red 122 may be contained in terms of color adjustment and color concentration adjustment. As other colorants, there are no particular limitations as long as they can achieve the desired color development when forming the colored layer of the color filter. Various organic pigments, inorganic pigments, dispersible dyes, and salt-formed dyes of dyes can be used. A compound etc. are used individually or in mixture of 2 or more types. The total content ratio of the other coloring materials is, for example, 10% by mass or less, preferably 5% by mass or less, relative to the total amount of the coloring materials, in terms of being able to form a colored layer with high brightness and reduced retardation. More preferably, it is 2 mass % or less, and may be 0 mass %.

As another coloring material, other red coloring material, orange coloring material, yellow coloring material, etc. are mentioned. Examples of other red coloring materials and orange coloring materials include naphthol-based azo pigments or other azo pigments, quinacridone-based pigments different from Pigment Red 202 and C.I. , Anthraquinone-based pigments, pyrene-based pigments, perylene-based pigments, thioindigo-based pigments, etc. Examples of yellow colorants include: C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 55, 60, 61, 65, 71, 73, 74, 81 ,83,93,95,97,98,100,101,104,106,108,109,110,113,114,116,117,119,120,126,127,128,129,138,139,150 , 151, 152, 153, 154, 155, 156, 166, 168, 175, 185, and derivative pigments of C.I. Pigment Yellow 150; C.I. Disperse Yellow 54, 64, 67, 134, 149, 160, C.I. Solvent Yellow 114 , 157 and other quinophthalone dyes, etc.

As a derivative pigment of C.I. Pigment Yellow 150, specifically, a metal complex compound of at least one anion and at least one metal ion of the following at least one anion selected from the host as at least one guest compound can be exemplified. A group consisting of mono-, di-, tri- and tetra-anions of azo compounds of the following chemical formula (ii) or one of their tautomeric structures, wherein at least one metal is selected from the group consisting of Li, Cs, Mg, Cd, Co , Al, Cr, Sn, Pb, Na, K, Ca, Sr, Ba, Zn, Fe, Ni, Cu, Mn and La. Particularly suitable examples of the metal ions include at least one metal ion selected from the group consisting of Na, K, Ca, Sr, Ba, Zn, Fe, Ni, Cu, Mn, and La. If such a derivative pigment of C.I. Pigment Yellow 150 is used, the brightness is improved, which is preferable.

[Chemical 3] formula (ii) (In the above chemical formula, R are independently OH, NH ₂ , NH-CN, acylamine, alkylamine, or arylamine, and R' are independently -OH or -NH ₂ )

Among them, in terms of improving brightness and contrast, the yellow coloring material is preferably a mono-, di-, or azo compound selected from the azo compounds represented by the above general formula (ii) and their tautomeric structures. Ions of at least one anion in the group consisting of three and four anions, and at least two metals selected from the group consisting of Cd, Co, Al, Cr, Sn, Pb, Zn, Fe, Ni, Cu, and Mn . As the at least two metals, among them, preferably at least one metal that becomes a divalent or trivalent cation, preferably at least one selected from the group consisting of Ni, Cu, and Zn, and more preferably Contains at least Ni. More preferably, it contains Ni and at least one metal selected from the group consisting of Zn, Cu, Al, and Fe. Among them, the above-mentioned at least two metals are preferably Ni and Zn, or Ni and Cu. The detailed description of the derivative pigment of C.I. Pigment Yellow 150 is the same as paragraphs 0031 to 0046 of JP-A-2017-003995, and the content of this publication is incorporated into this specification by reference.

The average primary particle size of the coloring material used in the present invention is not particularly limited as long as it can realize the desired color development when the coloring layer of the color filter is made, and it is also determined according to the coloring material used. It varies depending on the type, but it is preferably in the range of 10-100 nm, more preferably 15-60 nm. By making the average primary particle diameter of a coloring material into the said range, the display device equipped with the color filter manufactured using the photosensitive coloring resin composition of this invention can be made into high contrast and high quality.

Also, the average dispersed particle size of the coloring material in the photosensitive colored resin composition also varies depending on the type of coloring material used, and is preferably in the range of 10 to 100 nm, more preferably in the range of 15 to 60 nm. within the range of nm. The average dispersed particle size of the colorant in the photosensitive colored resin composition is the dispersed particle size of the colorant particles dispersed in a dispersion medium containing at least a solvent, and is measured by a laser light scattering particle size distribution analyzer. When using a laser light scattering particle size distribution analyzer to measure the particle size, the solvent used in the photosensitive colored resin composition can be used to dilute the photosensitive colored resin composition appropriately (for example, 1000 times, etc.) to a particle size that can be scattered by laser light The concentration measured by the distribution meter is measured at 23° C. by the dynamic light scattering method using a laser light scattering particle size distribution meter (for example, Nanotrac particle size distribution measuring device UPA-EX150 manufactured by Nikkiso Co., Ltd.). The average particle size distribution here is the volume average particle size.

The colorant used in the present invention can be produced by known methods such as recrystallization method and solvent-salt milling method. In addition, commercially available colorants can also be used by subjecting them to miniaturization treatment.

In the photosensitive colored resin composition of the present invention, the content of the colorant is not particularly limited. In terms of dispersibility and dispersion stability, the total content of the colorants is, for example, preferably 3% by mass to 65% by mass, more preferably 4% by mass relative to the total solid content of the photosensitive colored resin composition. % to 60% by mass. When it is more than the said lower limit, the colored layer when apply|coating a photosensitive coloring resin composition to predetermined film thickness (normally 1.0 micrometer - 5.0 micrometers) has sufficient color density. Moreover, it is excellent in storage stability as it is below the said upper limit, and the colored layer which has sufficient hardness and the adhesiveness with a board|substrate can be obtained. Especially in the case of forming a colored layer with a high concentration of coloring material, the total content of the coloring material is preferably 15% by mass to 65% by mass, more preferably Within the range of 25% by mass to 60% by mass. In addition, in this invention, solid content is all components except the following solvent, and also includes the monomer etc. which melt|dissolve in a solvent.

[Alkali-soluble resin] The alkali-soluble resin in the present invention has an acidic group, and can be appropriately selected from those that function as a binder resin and are soluble in an alkaline developer used for pattern formation. In the present invention, the alkali-soluble resin may have an acid value of 40 mgKOH/g or more as a standard. The preferred alkali-soluble resins in the present invention have acidic groups, usually carboxyl resins, specifically, for example: (meth)acrylic copolymers with carboxyl groups and styrene-(methyl) copolymers with carboxyl groups (meth)acrylic resins such as acrylic copolymers, epoxy (meth)acrylate resins having carboxyl groups, and the like.

Among them, those having a carboxyl group in the side chain and further having a photopolymerizable functional group such as an ethylenically unsaturated group in the side chain are particularly preferable. In the case of containing a photopolymerizable functional group, the alkali-soluble resins, or the alkali-soluble resin and a photopolymerizable compound such as a polyfunctional monomer, can form crosslinks during the hardening step of the resin composition during color filter production. Linkage. In the case of containing photopolymerizable functional groups, the strength of the film is improved, so even in the post-baking, the pigments are not easy to aggregate, and the phase difference can be continuously maintained at a low level. In addition, the film strength of the cured film is improved, the development resistance is improved, the heat shrinkage of the cured film is suppressed, and the adhesiveness with the substrate becomes excellent. The method for introducing an ethylenically unsaturated bond into the alkali-soluble resin may be appropriately selected from conventionally known methods. For example, a compound having an epoxy group and an ethylenically unsaturated bond in the molecule added to the carboxyl group of an alkali-soluble resin, such as glycidyl (meth)acrylate, etc., and ethylenically unsaturated bonds are introduced into the side chain The method of saturated bonds; or the method of introducing a structural unit having a hydroxyl group into a copolymer in advance, adding a compound having an isocyanate group and an ethylenically unsaturated bond in the molecule, and introducing an ethylenically unsaturated bond into the side chain; wait.

Moreover, it is preferable that alkali-soluble resin further has a hydrocarbon ring from the point which is excellent in the adhesiveness of a colored layer. By having a bulky hydrocarbon ring in the alkali-soluble resin, the shrinkage during curing is suppressed, the peeling between the substrate and the substrate is eased, and the substrate adhesion is improved. Examples of such hydrocarbon rings include aliphatic hydrocarbon rings that may have substituents, aromatic hydrocarbon rings that may have substituents, and combinations thereof. The hydrocarbon rings may have alkyl, carbonyl, carboxyl, oxycarbonyl, acyl Amino group, hydroxyl group, nitro group, amino group, halogen atom and other substituents. A hydrocarbon ring may be included as a monovalent group, or may be included as a divalent or higher group.

Specific examples of hydrocarbon rings include cyclopropane, cyclobutane, cyclopentane, cyclohexane, nor-ale, isobornane, tricyclo[5.2.1.0(2,6)]decane (dicyclo[5.2.1.0(2,6)]decane, Cyclopentane), adamantane and other aliphatic hydrocarbon rings; benzene, naphthalene, anthracene, phenanthrene, stilbene and other aromatic hydrocarbon rings; biphenyl, terphenyl, diphenylmethane, triphenylmethane, stilbene and other chain poly A ring, or a Cardo structure (9,9-diaryl oxane); a part of these groups is substituted with a substituent, etc. As said substituent, an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, a hydroxyl group, a carbonyl group, a nitro group, an amino group, a halogen atom, etc. are mentioned.

When an aliphatic hydrocarbon ring is contained as a hydrocarbon ring, the heat resistance or adhesiveness of a colored layer improves, and the brightness|luminance of the obtained colored layer improves, and it is preferable in this point. In addition, when the above-mentioned Cardo structure is included, the curability of the colored layer is improved, the fading of the colorant is suppressed, and the solvent resistance (NMP (N-Methyl-2-Pyrolidone, N-methyl-2-pyrrolidone) swelling Inhibition) promotion is particularly preferred in this regard.

(Meth)acrylic resins such as a (meth)acrylic copolymer having a structural unit having a carboxyl group, and a styrene-(meth)acrylic copolymer having a carboxyl group, etc., are made, for example, by a known method. The (co)polymer obtained by (co)polymerizing the ethylenically unsaturated monomer and other monomers that can be copolymerized as needed. Examples of carboxyl group-containing ethylenically unsaturated monomers include (meth)acrylic acid, vinyl benzoic acid, maleic acid, monoalkyl maleic acid, fumaric acid, and Conic acid, crotonic acid, cinnamic acid, acrylic acid dimer, etc. In addition, addition of a monomer having a hydroxyl group such as 2-hydroxyethyl (meth)acrylate to a cyclic anhydride such as maleic anhydride, phthalic anhydride, or cyclohexanedicarboxylic anhydride can also be used. Reactant, ω-carboxy-polycaprolactone mono(meth)acrylate, etc. Also, monomers containing acid anhydrides such as maleic anhydride, itaconic anhydride, and citraconic anhydride can be used as carboxyl group precursors. Among them, (meth)acrylic acid is particularly preferable in terms of copolymerizability, cost, solubility, glass transition temperature, and the like.

The alkali-soluble resin in the present invention is preferably a carboxyl-containing copolymer such as a (meth)acrylic copolymer having a structural unit having a carboxyl group and a structural unit having a hydrocarbon ring, and a styrene-(meth)acrylic copolymer. , more preferably a (meth)acrylic copolymer and a styrene-(meth)acrylic copolymer having a structural unit having a carboxyl group, a structural unit having a hydrocarbon ring, and a structural unit having an ethylenically unsaturated bond Carboxyl-containing copolymers.

As the ethylenically unsaturated monomer having a hydrocarbon ring, for example, cyclohexyl (meth)acrylate, dicyclopentyl (meth)acrylate, adamantyl (meth)acrylate, iso(meth)acrylate Benzyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, styrene, etc. are effective in maintaining the cross-sectional shape of the developed colored layer even during heat treatment , preferably using at least one selected from cyclohexyl (meth)acrylate, dicyclopentyl (meth)acrylate, adamantyl (meth)acrylate, benzyl (meth)acrylate, and styrene .

This carboxyl group-containing copolymer may further contain other structural units such as methyl (meth)acrylate, ethyl (meth)acrylate, and other structural units having ester groups. The structural unit having an ester group functions not only as a component that suppresses the alkali solubility of the colored resin composition but also as a component that improves solubility in solvents and solvent resolubility.

The carboxyl-containing copolymer can be made into an alkali-soluble resin with desired properties by properly adjusting the addition amount of each structural unit. The amount of the carboxyl group-containing ethylenically unsaturated monomer to be added is preferably at least 5% by mass, more preferably at least 10% by mass, based on the total amount of the monomers, from the viewpoint that a good pattern can be obtained. On the other hand, in terms of suppressing film roughness on the surface of the pattern after development, the amount of the carboxyl group-containing ethylenically unsaturated monomer added is preferably 50% by mass or less, more preferably 40% by mass or less.

In addition, among carboxyl group-containing copolymers such as acrylic copolymers having structural units having ethylenically unsaturated bonds and styrene-acrylic copolymers, which can be more preferably used as alkali-soluble resins, compared with carboxyl group-containing ethylenically unsaturated bond-containing copolymers, The added amount of the saturated monomer, the compound having both the epoxy group and the ethylenically unsaturated bond, is preferably from 10% by mass to 95% by mass, more preferably from 15% by mass to 90% by mass.

The preferred mass average molecular weight (Mw) of the carboxyl group-containing copolymer is preferably in the range of 1,000-50,000, more preferably 3,000-20,000. When it is 1,000 or more, the adhesive function after hardening improves, and when it is 50,000 or less, when it develops with an alkaline developing solution, pattern formation will become favorable. Furthermore, the mass average molecular weight (Mw) of the alkali-soluble resin can be measured by using polystyrene as a standard substance and THF (Tetrahydrofuran, tetrahydrofuran) as an eluent, using Shodex GPC System-21H (Shodex GPC System-21H).

The epoxy (meth)acrylate resin having a carboxyl group is not particularly limited, and epoxy (meth)acrylate resin obtained by reacting an epoxy compound with an unsaturated group-containing monocarboxylic acid and an acid anhydride is suitable. base) acrylate compounds. Epoxy compounds, unsaturated group-containing monocarboxylic acids, and acid anhydrides can be appropriately selected from known ones and used. The epoxy (meth)acrylate resin having a carboxyl group also preferably has the above-mentioned hydrocarbon ring in the molecule. Among them, the curability of the colored layer is improved, the fading of the coloring material is suppressed, and the residual film rate of the colored layer becomes high. In this respect, it is preferred to include a Cardo structure. The epoxy (meth)acrylate resin which has a carboxyl group may be used individually by 1 type, and may use 2 or more types together.

From the point of view of developability (solubility) to an alkaline aqueous solution used as a developer, it is preferable to use an alkali-soluble resin having an acid value of 40 mgKOH/g or more. The alkali-soluble resin preferably has an acid value of 40 mgKOH/g or more and 300 mgKOH/g or less in terms of developability (solubility) to an alkaline aqueous solution used as a developer and adhesion to a substrate , wherein, preferably not less than 50 mgKOH/g and not more than 280 mgKOH/g.

With respect to the ethylenically unsaturated bond equivalent when the side chain of the alkali-soluble resin has an ethylenically unsaturated group, the film strength of the cured film is improved, it is easy to maintain a low phase difference, the development resistance is improved, and the adhesion to the substrate is excellent, etc. In terms of effect, the range of 100-2000 is preferable, the range of 140-1500 is more preferable, and the range of 140-1000 may be used. When this ethylenically unsaturated bond equivalent is below the upper limit, it will be easy to maintain a low phase difference, and it will be excellent in image development resistance and adhesiveness. Moreover, if it is more than the lower limit, since the ratio of other structural units, such as the structural unit which has the said carboxyl group, or the structural unit which has a hydrocarbon ring, can increase relatively, it is excellent in developability and heat resistance. Here, the ethylenically unsaturated bond equivalent means the mass average molecular weight per mole of ethylenically unsaturated bond in the above-mentioned alkali-soluble resin, and is represented by the following numerical formula (1).

Mathematical formula (1) Ethylenic unsaturated bond equivalent (g/mol)=W(g)/M(mol) (In formula (1), W represents the mass (g) of the alkali-soluble resin, and M represents the molar number (mol) of ethylenically unsaturated bonds contained in the alkali-soluble resin W (g))

Regarding the above-mentioned ethylenically unsaturated bond equivalent, for example, the number of ethylenically unsaturated bonds contained in 1 g of alkali-soluble resin can be measured according to the test method of iodine value described in JIS K 0070:1992, thereby calculating the above-mentioned Ethylenically unsaturated bond equivalent.

The alkali-soluble resin used for the photosensitive colored resin composition may be used individually by 1 type, and may use it in combination of 2 or more types. The content of the alkali-soluble resin is not particularly limited, but is, for example, preferably 5% by mass to 60% by mass, more preferably 10% by mass to 40% by mass relative to the total solid content of the photosensitive colored resin composition % range. If the content of the alkali-soluble resin is more than the above lower limit, sufficient alkali developability can be obtained, and if the content of the alkali-soluble resin is below the above upper limit, film roughness or pattern loss can be suppressed during development.

[Photopolymerizable compound] The photopolymerizable compound used in the photosensitive colored resin composition of the present invention is not particularly limited as long as it can be polymerized by a photoinitiator, and usually a compound having two or more ethylenically unsaturated bonds is preferably used , especially preferably a polyfunctional (meth)acrylate having two or more acryl groups or methacryl groups. As such a polyfunctional (meth)acrylate, what is necessary is just to select suitably from well-known thing beforehand, and to use it. As a specific example, what is described in Unexamined-Japanese-Patent No. 2013-029832, etc. are mentioned, for example.

These polyfunctional (meth)acrylates may be used individually by 1 type, and may use it in combination of 2 or more types. Also, in terms of requiring excellent photocurability to the photosensitive colored resin composition of the present invention, the polyfunctional (meth)acrylate is preferably a compound having three or more (trifunctional) ethylenically unsaturated bonds, More preferably, it is a compound containing 3-15 ethylenically unsaturated bond groups, and it is still more preferable that it is a compound containing 3-6 ethylenically unsaturated bond groups. Moreover, the polymeric compound is preferably a 3-15 functional (meth)acrylate compound, more preferably a 3-6 functional (meth)acrylate compound. As a compound having three or more (trifunctional) ethylenically unsaturated bonds, for example, poly(meth)acrylates of polyhydric alcohols with three or more valences or their dicarboxylic acid modified products are preferred, specifically , preferably trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, succinic acid modified pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, Dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol penta(meth)acrylate modified succinic acid, dipentaerythritol hexa(meth)acrylate, etc.

The photopolymerizable compound used for the photosensitive colored resin composition of this invention may contain the photopolymerizable compound which has an acidic group from a developable point. The acid group may, for example, be a carboxyl group, a sulfo group or a phosphoric acid group, and is preferably a carboxyl group. As a commercial item of the photopolymerizable compound which has an acidic group, ARONIX M-510, M-520, ARONIX TO-2349 (made by Toagosei Co., Ltd.) etc. are mentioned. As for the content of the photopolymerizable compound having an acidic group in the photopolymerizable compound used in the photosensitive colored resin composition of the present invention, in terms of developability, it can be 20% to the total amount of photopolymerizable compound. It may be less than mass %, may be less than 10 mass %, may be less than 5 mass %, and may be 0 mass % at the point of the acid value of the said alkali-soluble resin combined.

The photopolymerizable compound used in the photosensitive coloring resin composition of the present invention may contain a photopolymerizable compound having a caprolactone structure in terms of facilitating adjustment of curability, easy formation of fine patterns, and easy suppression of omissions. compound. The photopolymerizable compound which has a caprolactone structure should just have the structure which opened the ring of ε-caprolactone, and may contain the structure which opened the ring of ε-caprolactone as a repeating unit. A photopolymerizable compound having a caprolactone structure can be obtained, for example, by esterifying alcohol, (meth)acrylic acid, and ε-caprolactone. Among them, polyhydric alcohol, (meth)acrylic acid, and ε-caprolactone are preferably used. A compound obtained by esterification of ε-caprolactone. A commercial item can also be used suitably as a photopolymerizable compound which has a caprolactone structure. As a commercial product, for example, the KAYARAD DPCA series commercially available from Nippon Kayaku Co., Ltd. Regarding the content of the photopolymerizable compound having a caprolactone structure in the photopolymerizable compound used in the photosensitive colored resin composition of the present invention, in terms of adjusting curability, relative to the total amount of the photopolymerizable compound, It may be 0 mass % - 70 mass %, and may be 10 mass % - 50 mass %.

In addition, the photopolymerizable compound used in the photosensitive colored resin composition of the present invention may contain an alkeneoxy group having an alkylene group, which is advantageous for adjusting curability, for forming a fine pattern, and for suppressing omission. Photopolymerizable compounds. The photopolymerizable compound having an alkoxyl group is preferably a photopolymerizable compound having an ethoxyl group and/or a propoxyl group, more preferably a photopolymerizable compound having an ethoxyl group, and more preferably a photopolymerizable compound having an ethoxyl group. 3-6 functional (meth)acrylate compounds with 4-20 ethoxy groups. As a commercial product of the photopolymerizable compound which has an alkyleneoxy group, for example, ethoxylated (4) pentaerythritol tetraacrylate (manufactured by Sando, SR-494), trimethylolpropane tripropoxy Dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD TPA-330), modified dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., trade name KAYARAD DPEA−12), NEW FRONTIER MF-001 manufactured by Daiichi Industrial Pharmaceutical Co., Ltd. As for the content of the photopolymerizable compound having an alkyleneoxy group in the photopolymerizable compound used in the photosensitive colored resin composition of the present invention, in terms of curability adjustment, relative to the total amount of the photopolymerizable compound, It may be 0 mass % - 50 mass %, and may be 5 mass % - 40 mass %.

The mass average molecular weight per mole of the photopolymerizable group of the photopolymerizable compound used in the photosensitive colored resin composition of the present invention, such as unsaturated bond equivalent, is preferably 300 in terms of curability or less, more preferably 250 or less, further preferably 200 or less. In terms of curability, the unsaturated bond equivalent may be 97 or less. The smaller the unsaturated bond equivalent, the better, and the lower limit may be about 50. The unsaturated bond equivalent here means the mass average molecular weight per mole of unsaturated bond of a photopolymerizable compound, and is represented by following numerical formula (2). Mathematical formula (2) Unsaturated bond equivalent (g/mol)=W2(g)/M2(mol) (In the formula (1), W2 represents the mass (g) of the photopolymerizable compound, and M2 represents the molar number (mol) of unsaturated bonds contained in the photopolymerizable compound W2 (g))

The content of the above-mentioned photopolymerizable compound used in the photosensitive colored resin composition is not particularly limited, but is preferably 5% by mass to 60% by mass, for example, with respect to the total solid content of the photosensitive colored resin composition Furthermore, it is more preferable to exist in the range of 10 mass % - 40 mass %. If the content of the photopolymerizable compound is more than the above-mentioned lower limit, the photocuring will proceed sufficiently, and the dissolution of the exposed part during development can be suppressed. full.

[Photoinitiator] The initiator used in the photosensitive colored resin composition of the present invention is not particularly limited, and may be used alone or in combination of two or more of various known initiators. The initiator may, for example, be a polymerization initiator such as a thermal polymerization initiator or a photopolymerization initiator, and specifically, those described in JP-A-2013-029832 may, for example, be mentioned.

As the photoinitiator, for example, aromatic ketones, benzoin ethers, halomethyl oxadiazole (halomethyl oxadiazole) compounds, α-amino ketones, biimidazoles, N,N-dimethylamine Base benzophenone, halomethyl-S-tri-sulfur compounds, 9-oxosulfur , oxime esters, etc. As the photoinitiator, for example, the photoinitiator described in International Publication No. 2018/062105 may be mentioned, and in addition, a previously known photoinitiator may be appropriately selected and used.

In the present invention, it is preferable to use an oxime ester-based photoinitiator in terms of improving the curability of the coating film, suppressing aggregation of colorant particles during baking, and easily suppressing retardation.

As the oxime ester photoinitiator used in the present invention, for example, it can be selected from 1,2-octadiene-1-[4-(phenylthio)phenyl]-,2-(o-benzoyl oxime), Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(o-acetyloxime), Japanese Patent Laid-Open 2000 - Publication No. 80068, Japanese Patent Application Publication No. 2001-233842, Japanese Patent Application Publication No. 2010-527339, Japanese Patent Application Publication No. 2010-527338, Japanese Patent Application Publication No. 2013-041153, International Publication 2015/152153 Appropriate selection is made from the oxime ester-based photoinitiators described in Japanese Patent Application Laid-Open No. 2010-256891 and the like.

As the oxime ester-based photoinitiator used in the present invention, among them, it is preferable to contain the following in terms of improving the curability of the coating film, suppressing the aggregation of the colorant particles during baking, and easily suppressing the phase difference. At least one of the oxime ester compounds represented by the general formula (A).

[Chem. 4] General formula (A) (In the general formula (A), Z ¹ , Z ³ , Z ⁴ and Z ⁵ each independently represent a hydrogen atom, a linear or branched alkyl group with 1 to 12 carbons, a ring with 3 to 20 carbons Alkyl or phenyl, the above-mentioned alkyl, cycloalkyl, and phenyl may be substituted with a substituent selected from the group consisting of a halogen atom, an alkoxy group having 1 to 6 carbon atoms, and a phenyl group, Z ² represents an alkyl group with 1 to 20 carbon atoms substituted by a cycloalkyl group)

<Compound represented by general formula (A)> In the above general formula (A), as a linear or branched alkyl group having 1 to 12 carbon atoms in Z ¹ , Z ³ , Z ⁴ and Z ⁵ , For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second-butyl, third-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl base, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc. Examples of the cycloalkyl group having 3 to 20 carbon atoms in Z ¹ , Z ³ , Z ⁴ and Z ⁵ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclo Octyl, cyclooctadecyl, etc. The aforementioned cycloalkyl group in ^Z2 may be the same as the aforementioned cycloalkyl group having 3 to 20 carbon atoms, and is preferably cyclopentyl or cyclohexyl. As the above-mentioned alkyl group having 1 to 20 carbon atoms in ^Z2 , in addition to the straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms mentioned above, n-tetradecyl, n-hexadecyl , n-octadecyl, etc.

In addition, among Z ¹ , Z ³ , Z ⁴ and Z ⁵ , examples of the halogen atom which may be substituted for the above-mentioned alkyl group, cycloalkyl group and phenyl group include fluorine atom, chlorine atom, bromine atom and the like. Among Z ¹ , Z ³ , Z ⁴ and Z ⁵ , examples of the above-mentioned alkoxy group having 1 to 6 carbon atoms that may be substituted for the above-mentioned alkyl group, cycloalkyl group, and phenyl group include: methoxy, ethyl Oxygen, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, etc.

In the general formula (A), Z ¹ is preferably an alkyl group or a phenyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, or a phenyl group, and even more preferably For methyl. Also, in the general formula (A), Z ³ , Z ⁴ , and Z ⁵ are preferably hydrogen atoms, methyl groups, ethyl groups, n-propyl groups, or isopropyl groups from the viewpoint of brightness.

In general formula (A), Z ² is preferably an alkyl group having 1 to 14 carbons substituted by a cycloalkyl group having 5 to 6 carbons in terms of compatibility, and more preferably an alkyl group having 1 to 14 carbons substituted by a cycloalkyl group having 5 to 6 carbons. An alkyl group having 1 to 10 carbons substituted by a cycloalkyl group having a number of 5 to 6 is more preferably cyclohexylmethyl or cyclopentylmethyl, especially preferably cyclohexylmethyl.

Among them, as the photoinitiator represented by the above-mentioned general formula (A), an oxime ester compound represented by the following chemical formula (A-1) is preferable in terms of suppressing a decrease in brightness. As a commercial item, TR-PBG-3057 (made by Changzhou Qiangli Electronic New Material Co., Ltd.) etc. are mentioned, for example.

[Chemical 5] Chemical formula (A-1)

The photoinitiator represented by the above general formula (A) can be synthesized, for example, by referring to Japanese Patent Application Publication No. 2012-526185, using diphenyl sulfide or its derivatives, and depending on the materials used The photoinitiator represented by the above general formula (A) is synthesized by appropriately selecting the solvent, reaction temperature, reaction time, purification method, etc. Moreover, it can also acquire a commercial item suitably and use it.

The total content of the photoinitiator used in the photosensitive colored resin composition of the present invention is not particularly limited as long as it does not impair the effect of the present invention. Preferably it is 0.1 mass % - 12.0 mass %, More preferably, it exists in the range of 1.0 mass % - 8.0 mass %. If the content is more than the above-mentioned lower limit, the photocuring will proceed sufficiently, and the elution of the exposed part during development will be suppressed. On the other hand, if it is below the above-mentioned upper limit, the yellowing of the obtained colored layer will be suppressed. The brightness is reduced. In addition, the solid content means all components except a solvent, and also includes a liquid polyfunctional monomer etc.

When the above-mentioned photoinitiator contains an oxime ester photoinitiator, in terms of improving the curability, the total content of the oxime ester photoinitiator in 100% by mass of the total amount of the photoinitiator is The lower limit may be 50 mass % or more, 60 mass % or more, and the upper limit may be 100 mass %, 90 mass % or less, or 80 mass % or less. When the above-mentioned photoinitiator contains at least one kind selected from the group consisting of the compounds represented by the above-mentioned general formula (A), in terms of solvent resistance, the total amount of the photoinitiator is 100% by mass Among them, the lower limit of the total content of one or more selected from the group consisting of the compounds represented by the above general formula (A) may be 10% by mass or more, 20% by mass or more, 30% by mass or more, or 50% by mass or more, may be 60% by mass or more, and the upper limit may be 100% by mass.

[solvent] The solvent used in the present invention is not particularly limited as long as it is an organic solvent that can dissolve or disperse the components in the photosensitive colored resin composition without reacting with them. A solvent can be used individually or in combination of 2 or more types. As specific examples of solvents, for example, alcohol-based solvents such as methanol, ethanol, N-propanol, isopropanol, methoxy alcohol, and ethoxy alcohol; Carbitol-based solvents such as oxyethanol; ethyl acetate, butyl acetate, methyl methoxypropionate, ethyl methoxypropionate, ethyl ethoxypropionate, ethyl lactate, methyl hydroxypropionate Esters, ethyl hydroxypropionate, n-butyl acetate, isobutyl acetate, isobutyl butyrate, n-butyl butyrate, ethyl lactate, cyclohexyl acetate and other ester solvents; acetone, methyl ethyl ketone , methyl isobutyl ketone, cyclohexanone, 2-heptanone and other ketone solvents; methoxyethyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy-3-methyl-1-acetate Butyl, 3-methoxybutyl acetate, ethoxyethyl acetate and other glycol ether acetate solvents; methoxyethoxyethyl acetate, ethoxyethoxyethyl acetate, butyl Carbitol acetate-based solvents such as carbitol acetate (BCA); diacetates such as propylene glycol diacetate and 1,3-butanediol diacetate; ethylene glycol monomethyl ether, ethyl Glycol ether solvents such as glycol monoethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, and dipropylene glycol dimethyl ether ; Aprotic amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; Lactone-based solvents such as γ-butyrolactone; Tetrahydrofuran Cyclic ether solvents; benzene, toluene, xylene, naphthalene and other unsaturated hydrocarbon solvents; N-heptane, N-hexane, N-octane and other saturated hydrocarbon solvents; toluene, xylene and other aromatic hydrocarbons and other organic solvents. Among these solvents, glycol ether acetate-based solvents, carbitol acetate-based solvents, glycol ether-based solvents, and ester-based solvents are suitably used from the point of solubility of other components. Among them, as the solvent used in the present invention, it is preferably selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, butyl carbitol ethyl alcohol in terms of solubility of other components or coating adaptability. Acetate (BCA), 3-methoxy-3-methyl-1-butyl acetate, ethyl ethoxypropionate, ethyl lactate, and 3-methoxybutyl acetate more than one.

In the photosensitive colored resin composition of this invention, content of a solvent should just be set suitably within the range which can form a colored layer with high precision. The content of the solvent is usually within a range of preferably 55% by mass to 95% by mass, more preferably 65% by mass to 88% by mass relative to the total amount of the photosensitive colored resin composition including the solvent. Coatability can be made excellent by making content of the said solvent into the said range.

[Dispersant] When dispersing a coloring material in the photosensitive colored resin composition of this invention, you may contain a dispersing agent further from the point of coloring material dispersibility and coloring material dispersion stability. In the present invention, the dispersant can be appropriately selected from conventionally known dispersants and used. As the dispersant, for example, cationic, anionic, nonionic, amphoteric, silicone-based, fluorine-based or other surfactants can be used. Among the surfactants, polymer dispersants are preferred in terms of being able to disperse uniformly and finely.

Examples of polymer dispersants include: (meth)acrylate copolymer-based dispersants; polyurethanes; unsaturated polyamides; polysiloxanes; Phosphates; polyethyleneimine derivatives (amides or bases thereof obtained by reacting poly(lower alkyleneimines) with polyesters containing free carboxyl groups); polyallylamine derivatives (using Polyallylamine, a reaction product obtained by reacting with one or more compounds selected from polyesters having free carboxyl groups, polyamides, or cocondensates of esters and amides (polyesteramides), etc.

In the present invention, it is preferable to use a (meth)acrylate copolymer-based dispersant as a dispersant from the point of view of controlling developability. Since the (meth)acrylate copolymer-based dispersant has good compatibility with the above-mentioned alkali-soluble resin and the above-mentioned photopolymerizable compound, it is estimated that generation of image development residue can be suppressed.

In the present invention, the (meth)acrylate copolymer-based dispersant is a copolymer, and means a dispersant containing at least a structural unit derived from (meth)acrylate. The (meth)acrylate copolymer-based dispersant is preferably a copolymer containing a structural unit that functions as a colorant adsorption site and a structural unit that functions as a solvent-affinity site. The functional structural unit includes at least a (meth)acrylate-derived structural unit.

Structural units that function as colorant adsorption sites include structural units derived from ethylenically unsaturated monomers that can be copolymerized with structural units derived from (meth)acrylates. The colorant adsorption site may be a structural unit derived from an acidic group-containing ethylenically unsaturated monomer, or a structural unit derived from a basic group-containing ethylenically unsaturated monomer. As the structural unit derived from the basic group-containing ethylenically unsaturated monomer, a structural unit represented by the following general formula (I) is preferable in terms of excellent dispersibility of the above-mentioned colorant.

[chemical 6] (In general formula (I), R ¹ represents a hydrogen atom or a methyl group, A ¹ represents a divalent linking group, R ² and R ³ independently represent a hydrogen atom or a hydrocarbon group that may contain heteroatoms, R ² and R ³ can be bonded to each other to form a ring structure)

In the general formula (I), A ¹ is a divalent linking group. As the divalent linking group, for example, a linear, branched or cyclic alkylene group, a linear, branched or cyclic alkylene group having a hydroxyl group, an arylylene group, -CONH- group, - COO-group, -NHCOO-group, ether group (-O-group), thioether group (-S-group), combinations thereof, etc. Furthermore, in the present invention, the orientation of the bonding of the divalent linking group is arbitrary. That is, when -CONH- is included in the divalent linking group, -CO may be the carbon atom side of the main chain and -NH may be the nitrogen atom side of the side chain, or conversely, -NH may be the carbon atom of the main chain atom side and -CO is the nitrogen atom side of the side chain. Among them, in terms of dispersibility, ^A1 in the general formula (I) is preferably a divalent linking group comprising -CONH- or -COO-, more preferably comprising -CONH- or -COO- group, and a divalent linking group of an alkylene group having 1 to 10 carbon atoms.

Regarding the hydrocarbon group in the hydrocarbon group that may contain heteroatoms in R ² and R ³ , for example, an alkyl group, an aralkyl group, an aryl group, etc. can be exemplified. As the alkyl group, for example, methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2-ethylhexyl, cyclopentyl, cyclohexyl, etc., the carbon number of the alkyl group is preferable is 1 to 18, and among them, methyl or ethyl is more preferable. As an aralkyl group, a benzyl group, a phenethyl group, a naphthylmethyl group, a biphenylmethyl group etc. are mentioned, for example. The carbon number of an aralkyl group becomes like this. Preferably it is 7-20, More preferably, it is 7-14. Moreover, as an aryl group, a phenyl group, a biphenylyl group, a naphthyl group, a tolyl group, a xylyl group, etc. are mentioned. The carbon number of the aryl group is preferably 6-24, more preferably 6-12. Furthermore, the above-mentioned preferred carbon number does not include the carbon number of the substituent. The hydrocarbon group containing heteroatoms has a structure in which carbon atoms in the above hydrocarbon group are replaced by heteroatoms, or a structure in which hydrogen atoms in the above hydrocarbon group are replaced by substituents containing heteroatoms. Examples of heteroatoms that may be included in the hydrocarbon group include oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms. In addition, hydrogen atoms in the hydrocarbon group may be substituted by halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and the like.

R ² and R ³ are bonded to each other to form a ring structure, which means that R ² and R ³ form a ring structure via a nitrogen atom. The ring structure formed by R ² and R ³ may contain heteroatoms. The ring structure is not particularly limited, and examples thereof include a pyrrolidine ring, a piperidine ring, and a thioline ring.

In the present invention, it is preferred that R ² and R ³ are independently hydrogen atoms, alkyl groups with 1 to 5 carbons, and phenyl groups, or that R ² and R ³ are bonded to form a pyrrolidine ring or a piperidine ring. , 𠰌line ring.

As the monomer from which the structural unit represented by the above-mentioned general formula (I) is derived, dimethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, (methyl) Diethylaminoethyl acrylate, diethylaminopropyl (meth)acrylate and other (meth)acrylates containing alkyl-substituted amino groups, etc., dimethylaminoethyl (meth)acrylamide , dimethylaminopropyl (meth)acrylamide, etc. (meth)acrylamide containing an amino group substituted by an alkyl group, etc. Among them, in terms of improving dispersibility and dispersion stability, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylamide. In the polymer, the structural unit represented by the general formula (I) may consist of only one kind, or may contain two or more kinds of structural units.

In addition, regarding the structural unit functioning as a colorant adsorption site, at least a part of the nitrogen site contained in the structural unit represented by the above general formula (I), and at least one of the nitrogen sites selected from the group consisting of organic acid compounds and halogenated hydrocarbons One can form salts. As the organic acid compound, an acidic organic phosphorus compound such as phenylphosphonic acid or phenylphosphinic acid is preferable in terms of excellent dispersibility and dispersion stability of the coloring material. As a specific example of the organic acid compound used for such a dispersant, the organic acid compound described in Unexamined-Japanese-Patent No. 2012-236882 etc. is mentioned as a preferable one, for example. In addition, the above-mentioned halogenated hydrocarbon is preferably at least one of allyl halides such as allyl bromide and benzyl chloride, and aralkyl halides in terms of excellent dispersibility and dispersion stability of the colorant.

The copolymer having the structural unit represented by the above-mentioned general formula (I) is more preferably at least one of the following graft copolymers and the following block copolymers in terms of dispersibility and dispersion stability. The graft copolymer has a structural unit represented by the above-mentioned general formula (I) and has a structural unit derived from (meth)acrylate in the graft polymer chain, and the above-mentioned block copolymer has The A block of the structural unit represented, and the B block containing the structural unit derived from (meth)acrylate. Hereinafter, the above-mentioned graft copolymer and the above-mentioned block copolymer will be described in order.

As a graft copolymer having a structural unit represented by the above-mentioned general formula (I) and having a structural unit derived from (meth)acrylate in the graft polymer chain, it can be exemplified: The structural unit represented, the graft copolymer with the structural unit represented by the following general formula (II), and at least a part of the nitrogen site of the structural unit represented by the general formula (I) in the graft copolymer , At least one of the salt-type graft copolymers obtained by forming a salt with at least one selected from the group consisting of organic acid compounds and halogenated hydrocarbons.

[chemical 7] (In the general formula (II), R ^1' represents a hydrogen atom or a methyl group, A ² represents a direct bond or a divalent linking group, Polymer represents a polymer chain, and the structural units of the polymer chain include those derived from (methyl) Structural unit of acrylate)

In the above general formula (II), A ² is a direct bond or a divalent linking group. The divalent linking group in ^A2 is not particularly limited as long as it can link a carbon atom derived from an ethylenically unsaturated bond to a polymer chain. The divalent linking group in ^A2 may, for example, be the same as the divalent linking group in ^A1 above. Among them, in terms of dispersibility, ^A2 in the general formula (II) is preferably a divalent linking group comprising -CONH- or -COO-, more preferably comprising -CONH- or -COO- A group, a divalent linking group with an alkylene group having 1 to 10 carbon atoms.

In the above general formula (II), Polymer represents a polymer chain, and the structural units of the polymer chain include structural units derived from (meth)acrylate. By including the structural unit represented by the above-mentioned general formula (II) having a specific polymer chain, the graft copolymer makes the solvent affinity become good, the dispersibility and dispersion stability of the colorant become good, and it is compatible with the above-mentioned light The compatibility of the starter also becomes good. As the structural unit derived from (meth)acrylate contained in the polymer chain, the following general formula (III) in the structural unit represented by the following general formula ( ^III ) may include -COO A structural unit represented by the general formula (III) of the divalent linking group of the - group.

[chemical 8] (In the general formula (III), R ⁴ is a hydrogen atom or a methyl group, A ³ is a divalent linking group, R ¹⁰ is a hydrogen atom, or a hydrocarbon group that may contain heteroatoms)

As the divalent linking group of ^A3 , for example, the same ones as the divalent linking group in ^A1 above can be mentioned. In the present invention, as a structural unit derived from (meth)acrylate, it at least includes a structure represented by general formula (III) in which ^A in general formula (III) is a divalent linking group including -COO- group unit. In terms of solubility in organic solvents used in color filter applications, A ³ in the general formula (III) may include a divalent linking group including a -CONH- group.

Regarding the hydrocarbon group in the hydrocarbon group that may contain a heteroatom in R ¹⁰ , for example, combinations thereof such as an alkyl group, an alkenyl group, an aryl group, and an aralkyl group or an aryl group substituted by an alkyl group may be mentioned. As the hydrocarbon group in the hydrocarbon group that may contain a heteroatom in ^R10 , for example, an alkyl group having 1 to 18 carbons, an alkenyl group having 2 to 18 carbons, an aryl group, and an aralkyl group, or substituted by an alkyl group The combination of the aryl group and the like. The above-mentioned alkyl group having 1 to 18 carbon atoms may be any of linear, branched, and cyclic, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-nonyl radical, n-lauryl, n-stearyl, cyclopentyl, cyclohexyl, thiol, iso-thiol, dicyclopentyl, adamantyl, adamantyl substituted with lower alkyl, etc. The carbon number of the alkyl group is preferably 1-12, more preferably 1-6. The alkenyl group having 2 to 18 carbon atoms may be linear, branched or cyclic. As such an alkenyl group, a vinyl group, an allyl group, a propenyl group etc. are mentioned, for example. The position of the double bond of the alkenyl group is not limited, but it is preferable to have a double bond at the end of the alkenyl group in terms of the reactivity of the obtained polymer. The carbon number of the alkenyl group is preferably 2-12, more preferably 2-8. The aryl group may, for example, be a phenyl group, a biphenyl group, a naphthyl group, a tolyl group or a xylyl group. The carbon number of the aryl group is preferably 6-24, more preferably 6-12. Moreover, as an aralkyl group, a benzyl group, a phenethyl group, a naphthylmethyl group, a biphenylmethyl group etc. are mentioned, It may further have a substituent. The carbon number of an aralkyl group becomes like this. Preferably it is 7-20, More preferably, it is 7-14. In addition, a linear or branched alkyl group having 1 to 30 carbon atoms may be bonded to an aromatic ring such as the above-mentioned aryl group or aralkyl group as a substituent.

As the hydrocarbon group in ^R10 , in terms of dispersion stability, it is preferably an alkyl group selected from an alkyl group having 1 to 18 carbons, an aryl group having 6 to 12 carbons which may be substituted by an alkyl group, and an alkyl group which may be substituted by an alkyl group. One or more of the group consisting of aralkyl groups with 7 to 14 carbon atoms substituted by radicals, preferably selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, n-nonyl, n-lauric One or more of the group consisting of n-stearyl, n-stearyl, phenyl which may be substituted by alkyl and benzyl.

Examples of heteroatoms that may be included in the hydrocarbon group include oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms. Examples of hydrocarbon groups that may contain heteroatoms include -CO-, -COO-, -OCO-, -O-, -S-, -CO-S-, -S-CO- in the carbon chain of the hydrocarbon group. , -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O- The structure of the linking group such as NH-. In addition, the hydrocarbon group may have a substituent within a range that does not interfere with the dispersibility of the above-mentioned graft copolymer. Examples of substituents include halogen atoms, hydroxyl groups, carboxyl groups, alkoxy groups, nitro groups, and cyano groups. , epoxy group, isocyanate group, thiol group, etc.

In addition, the hydrocarbon group that may contain a heteroatom in R ¹⁰ may have a structure in which a polymerizable group such as an alkenyl group is added to the terminal of the hydrocarbon group via a linking group containing a heteroatom. For example, the structural unit represented by the general formula (III) may be a structure in which glycidyl (meth)acrylate is reacted with a structural unit derived from (meth)acrylic acid. That is, the structure of -A ³ -R ¹⁰ in the general formula (III) can be represented by -COO-CH ₂ CH(OH)CH ₂ -OCO-CR=CH ₂ (here, R is a hydrogen atom or a methyl group) representation structure. Moreover, the structural unit represented by general formula (III) may be the structure which made the 2-isocyanatoalkyl (meth)acrylate and the structural unit originating in the hydroxyalkyl (meth)acrylate react, for example. That is, R ¹⁰ in the general formula (III) can be -R'-OCONH-R''-OCO-CR=CH ₂ (here, R' and R'' are independently alkylene, R is hydrogen atom or methyl group) represents the structure.

As the monomer derived from the structural unit represented by the general formula (III), for example, it is preferred to have a monomer derived from methyl (meth)acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, ( n-butyl methacrylate, isobutyl (meth)acrylate, tertiary butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate ester, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, iso-(meth)acrylate, dicyclopentyl (meth)acrylate, (meth)acrylate Adamantyl acrylate, (meth)acrylic acid, 2-methacryloxyethyl succinate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, (meth)acrylate base) 2-hydroxybutyl acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, phenoxyethyl (meth)acrylate, methoxy Polyethylene glycol (meth)acrylate and structural units of polyethylene glycol (meth)acrylate, phenoxyethylene glycol (meth)acrylate, etc. However, it is not limited thereto.

In the present invention, as the above-mentioned R ¹⁰ , those having excellent solubility in the following organic solvents are preferably used, and they may be appropriately selected according to the organic solvent used for the colorant dispersion liquid. Specifically, for example, when the above-mentioned organic solvents are organic solvents such as ether alcohol acetates, ethers, esters, and alcohols that are generally used as organic solvents for colorant dispersions, it is preferable to use: methyl, Ethyl, isobutyl, n-butyl, 2-ethylhexyl, benzyl, cyclohexyl, dicyclopentyl, hydroxyethyl, phenoxyethyl, adamantyl, methoxypolyethylene glycol , Methoxy polypropylene glycol base, polyethylene glycol base, etc.

In terms of easily lowering the crystallinity of R202, which tends to significantly increase the phase difference, and easily reducing the phase difference, the above-mentioned graft copolymer is preferably a polymer in the structural unit represented by the above-mentioned general formula (II) The structural unit of the chain contains at least one structural unit selected from the group consisting of structural units represented by the following general formula (IV). The structural unit represented by the following general formula (IV) is a structural unit included in the structural unit represented by the above general formula (III).

[chemical 9] (In the general formula (IV), R ⁴ is a hydrogen atom or a methyl group, A ³ is a divalent linking group, R ⁵ is an ethyl or propyl group, R ⁶ is a hydrogen atom or a hydrocarbon group, m represents 2 to 30 following number)

As the divalent linking group of ^A3 , it can be the same as the above-mentioned general formula (III). Among them, in terms of solubility in organic solvents used in color filters, ^A3 in the general formula (IV) is preferably a divalent linking group containing a -CONH- group or a -COO- group , more preferably a -CONH- group or a -COO- group, and still more preferably a -COO- group.

The above-mentioned m represents the number of repeating units of the ethylene oxide chain or the propylene oxide chain, and may be 2 or more, or 4 or more, in terms of easily reducing the retardation, wherein, in terms of improving the dispersibility, it may be 19 or more, or 21 or more. When comprising the structural unit represented by the general formula (IV) in which the above-mentioned m is 19 or more, the above-mentioned graft copolymer contains a structural unit represented by the general formula (I) and a structural unit represented by the general formula (II) The main chain part, the structural unit represented by the above-mentioned general formula (II) contains the structural unit represented by the general formula (IV) in the polymer chain, and the structural unit represented by the general formula (IV) contains a specific repeating number Polyethylene oxide chains or polypropylene oxide chains. In the specific graft copolymer used in the present invention, the structural unit of the polymer chain thus grafted contains a structural unit having a polyethylene oxide chain or a polypropylene oxide chain having a specific repetition number, followed by The polymer chains of the branches themselves have a branched structure. A plurality of grafted polymer chains are three-dimensionally extended in the film, and the specific surface area becomes larger. Therefore, it is presumed that it is easy to maintain the pigment that has been miniaturized by dispersion in a state with low crystallinity.

The hydrocarbon group in ^R6 may be the same as the hydrocarbon group in ^R10 above. As the hydrocarbon group in ^R6 , among them, in terms of dispersion stability or compatibility, it is preferably an alkyl group selected from an alkyl group having 1 to 18 carbons, an aryl group having 6 to 12 carbons which may be substituted by an alkyl group , and one or more of the group consisting of an aralkyl group with 7 to 14 carbon atoms which may be substituted by an alkyl group, preferably selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, n- One or more of the group consisting of nonyl, n-lauryl, n-stearyl, phenyl which may be substituted with an alkyl group, and benzyl.

In the aforementioned polymer chain, at least one structural unit selected from the group consisting of structural units represented by the aforementioned general formula (IV) may be a single type, or two or more types may be mixed.

When the structural unit of the polymer chain in the structural unit represented by the above general formula (II) contains at least one structural unit selected from the group consisting of the structural unit represented by the above general formula (IV), the When the total structural units of the above-mentioned polymer chains are taken as 100% by mass, the total ratio of the structural units represented by the above general formula (IV) is preferably at least 10% by mass, more preferably 20% by mass, from the aspect of suppressing retardation. Mass % or more, more preferably 30 mass % or more, on the other hand, in terms of dispersion stability, compatibility with solvents and resists (resolvability), preferably 80 mass % or less, More preferably, it is 70 mass % or less, More preferably, it is 60 mass % or less.

In the above polymer chain, the structural unit represented by the above general formula (III) including the structural unit represented by the above general formula (IV) may be a single type or two or more types may be mixed. In terms of the dispersibility and dispersion stability of the colorant, when the total structural units of the polymer chain are taken as 100% by mass, the total ratio of the structural units represented by the above general formula (III) is preferably 70% by mass % or more, more preferably more than 90% by mass. On the other hand, in terms of dispersion stability, the total ratio of the structural units represented by the general formula (III) in the above-mentioned polymer chain is also It may be 100% by mass. Among them, in terms of dispersion stability, solvent resistance, and compatibility with initiators, when the total structural units of the polymer chain are taken as 100% by mass, the structure derived from (meth)acrylate The total ratio of the units is preferably at least 60% by mass, more preferably at least 80% by mass. On the other hand, in terms of simultaneously satisfying dispersion stability and excellent solvent resistance, in the above-mentioned polymer chain, when the total structural units of the polymer chain are taken as 100% by mass, The total ratio of the structural unit of an acrylate may be 100 mass %.

In the structural unit of the polymer chain among the structural units represented by the above-mentioned general formula (II) of the above-mentioned graft copolymer, other structural units may be contained in addition to the structural unit represented by the above-mentioned general formula (III). As the other structural unit, a structural unit derived from a monomer having an unsaturated bond that can be copolymerized with a monomer from which the structural unit represented by the above general formula (III) can be exemplified. Examples of monomers from which other structural units are derived include styrenes such as styrene and α-methylstyrene, vinyl ethers such as phenyl vinyl ether, and the like.

In the polymer chain in the structural unit represented by the above-mentioned general formula (II) of the above-mentioned graft copolymer, in terms of the effect of the present invention, when the total structural units of the polymer chain are taken as 100% by mass, The total ratio of other structural units is preferably at most 30% by mass, more preferably at most 10% by mass.

The mass average molecular weight Mw of the polymer chain in the polymer is preferably 2000 or more, more preferably 3000 or more, further preferably 4000 or more, and more preferably in terms of the dispersibility and dispersion stability of the colorant It is 15000 or less, more preferably 12000 or less. By being within the above range, sufficient steric repulsion effect as a dispersant can be maintained, and the specific surface area of the solvent-affinity part of the dispersant becomes large, thereby easily suppressing penetration of the solvent into the coating film or reaching the colorant.

In addition, the standard of the polymer chain in the polymer is preferably a solubility at 23° C. of 20 (g/100 g solvent) or higher with respect to an organic solvent used in combination. The solubility of the polymer chains can be determined based on the fact that the raw material for introducing the polymer chains in the preparation of the graft copolymer has the above-mentioned solubility. For example, when a polymerizable oligomer (macromonomer) containing a group having an ethylenically unsaturated bond is used in the polymer chain and its terminal in order to introduce a polymer chain into a graft copolymer, as long as the polymerizable It is sufficient that the oligomer has the above-mentioned solubility. Also, when a polymer chain containing a reactive group capable of reacting with a reactive group contained in the copolymer is used to introduce a polymer chain after forming a copolymer using a monomer containing a group having an ethylenically unsaturated bond , as long as the polymer chain containing the reactive group has the above-mentioned solubility.

In the above-mentioned graft copolymer, when the total structural unit of the main chain comprising the structural unit represented by the above-mentioned general formula (I) is set as 100% by mass, the structural unit represented by the above-mentioned general formula (I) is preferably represented by 3 It is contained at a ratio of mass % to 60 mass %, more preferably 6 mass % to 45 mass %, still more preferably 9 mass % to 30 mass %. If the structural unit represented by the general formula (I) in the graft copolymer is within the above range, the ratio of the affinity portion with the colorant in the graft copolymer becomes appropriate, and the dissolution of the organic solvent can be suppressed Therefore, the adsorption of the colorant becomes better, and it is easy to obtain excellent dispersibility and dispersion stability. On the other hand, in the above-mentioned graft copolymer, when the total structural unit of the main chain including the structural unit represented by the above-mentioned general formula (I) is set as 100% by mass, the structural unit represented by the above-mentioned general formula (II) is less than Preferably, it is contained in the ratio of 40 mass % - 97 mass %, More preferably, it is 55 mass % - 94 mass %, More preferably, it is 70 mass % - 91 mass %. If the structural unit represented by the general formula (II) in the graft copolymer is within the above range, the ratio of the solvent-affinity moiety in the graft copolymer becomes appropriate, and sufficient steric repulsion effect as a dispersant can be maintained , and the specific surface area of the solvent-affinity portion of the dispersant becomes larger, thereby easily inhibiting the penetration of the solvent into the coating film or reaching the colorant. In the above-mentioned graft copolymer, when the total structural unit of the main chain comprising the structural unit represented by the above-mentioned general formula (I) is set as 100% by mass, the structural unit represented by the above-mentioned general formula (I) and the above-mentioned general formula ( The total ratio of the structural units represented by II) is preferably at least 70% by mass, more preferably at least 90% by mass, and may be 100% by mass.

The above-mentioned graft copolymer used in the present invention can also have the following structure in addition to the structural unit represented by the above-mentioned general formula (I) and the structural unit represented by the above-mentioned general formula (II) within the scope of not impairing the effect of the present invention. other structural units. As other structural units, an ethylenically unsaturated bond-containing monomer that can be copolymerized with an ethylenically unsaturated bond-containing monomer derived from the structural unit represented by the above general formula (I) can be appropriately selected for copolymerization, and Import other structural units. As another structural unit copolymerized with the structural unit represented by the said general formula (I), the structural unit represented by the said general formula (III), etc. are mentioned, for example. Furthermore, the content ratio of the above-mentioned structural unit can be derived from the structural unit represented by the above-mentioned general formula (I), the structural unit represented by the above-mentioned general formula (II), and the above-mentioned Calculated based on the added amount of the monomer such as the structural unit represented by the general formula (III).

Moreover, the mass average molecular weight Mw of the above-mentioned graft copolymer is preferably 4000 or more, more preferably 6000 or more, and still more preferably 8000 or more in terms of dispersibility and dispersion stability. On the other hand, in terms of solvent resolubility, it is preferably 50,000 or less, more preferably 30,000 or less. Furthermore, in the present invention, the mass average molecular weight Mw is a value measured by GPC (gel permeation chromatography). The measurement can be carried out as follows: use HLC-8120GPC manufactured by Tosoh, set the dissolution solvent as N-methylpyrrolidone added with 0.01 mol/liter of lithium bromide, and set the polystyrene standard for the calibration curve as Mw377400, 210500, 96000, 50400, 20650, 10850, 5460, 2930, 1300, 580 (the above are Easi PS-2 series manufactured by Polymer Laboratories) and Mw1090000 (manufactured by Tosoh), and the measuring column is set as TSK-GEL ALPHA-M×2 pieces (manufactured by Tosoh).

Next, the block copolymer which has the A block containing the structural unit represented by the said general formula (I), and the B block containing the structural unit derived from (meth)acrylate is demonstrated. In the present invention, the arrangement of each block of the block copolymer is not particularly limited, and may be, for example, an AB block copolymer, ABA block copolymer, or BAB block copolymer. Among these, AB block copolymers or ABA block copolymers are preferable in terms of excellent dispersibility.

The A block is a block that functions as a colorant adsorption site, and includes at least the structural unit represented by the above-mentioned general formula (I). It may also be obtained by forming a salt with at least a part of the nitrogen site of the structural unit represented by the general formula (I) of the block copolymer and at least one selected from the group consisting of organic acid compounds and halogenated hydrocarbons. Salt type block copolymer. The A block may have a structural unit other than the structural unit represented by the general formula (I) within the scope of achieving the object of the present invention, and may contain a structural unit copolymerizable with the structural unit represented by the general formula (I). Specifically, for example, the structural unit represented by the above general formula (III), etc. are mentioned. In the A block in the block copolymer before salt formation, when the total structural units of the A block are taken as 100% by mass, the content ratio of the structural unit represented by the general formula (I) is preferably 50% by mass to 100% by mass, more preferably 80% by mass to 100% by mass, most preferably 100% by mass. The reason is that the higher the ratio of the structural unit represented by the general formula (I), the higher the adsorption force to the colorant is, and the better the dispersibility and dispersion stability of the block copolymer become. In addition, the content ratio of the said structural unit is calculated from the added mass when synthesizing the block which has the structural unit represented by general formula (I).

In the block copolymer before salt formation, in terms of dispersibility and dispersion stability, when the total structural units of the block copolymer are 100% by mass, the compound represented by the general formula (I) is included. The total content ratio of the total structural units of the A blocks of the structural units is preferably from 5% by mass to 60% by mass, more preferably from 10% by mass to 50% by mass. In addition, in the block copolymer before salt formation, in terms of dispersibility and dispersion stability, when the total structural units of the block copolymer are 100% by mass, the formula (I) The content ratio of the structural unit indicated is preferably from 5% by mass to 60% by mass, more preferably from 10% by mass to 50% by mass. In addition, the content ratio of each structural unit in the said block copolymer was calculated from the added mass at the time of the block copolymer before synthetic salt formation. Furthermore, as long as the structural unit represented by the general formula (I) has affinity with the coloring material, one kind may be included, and two or more kinds of structural units may be included.

The B block is a block functioning as a solvent-affinity site, and contains at least a (meth)acrylate-derived structural unit. The (meth)acrylate-derived structural unit may be the same as the (meth)acrylate-derived structural unit described in the above-mentioned graft copolymer. As the B block, it is preferable to use a monomer having an unsaturated bond that can be copolymerized with a monomer derived from the structural unit represented by the general formula (I), and use it in a manner that has solvent affinity according to the solvent. . As a standard, it is preferable to introduce the B block so that the solubility of the copolymer at 23° C. with respect to the solvent used in combination is 20 (g/100 g solvent) or more. The structural unit constituting the B block portion may contain one kind, or may contain two or more kinds of structural units. As a structural unit contained in B block, the structural unit represented by the said General formula (III), etc. are mentioned, for example.

In the block copolymer used as the dispersant of the present invention, the ratio of the number m of units that are structural units represented by the above general formula (I) to the number n of units constituting other structural units constituting the solvent affinity block portion m/n is preferably in the range of 0.01 to 1, and more preferably in the range of 0.05 to 0.7 in terms of the dispersibility and dispersion stability of the colorant.

Regarding the above-mentioned block copolymer, it is preferable that the structural unit contained in the B block contains a compound selected from the group consisting of the above-mentioned compounds in terms of reducing the crystallinity of R202, which tends to increase the retardation significantly, and easily reducing the retardation. At least one structural unit of the group consisting of structural units represented by the general formula (IV). At least one structural unit selected from the group consisting of structural units represented by the general formula (IV) contained in the above block copolymer may be the same as that described for the above graft copolymer. When the structural unit represented by the above-mentioned general formula (IV) in which the above-mentioned m is 19 or more is included, the block copolymer has a relatively long polyalkylene chain, so it expands three-dimensionally in the film, and the specific surface area becomes larger , so it is presumed that it is easy to maintain the pigment that has been miniaturized by dispersion in a state with low crystallinity.

In the block copolymer, when the total structural units of the block copolymer are taken as 100% by mass, the content ratio of at least one structural unit selected from the group consisting of the structural units represented by the above general formula (IV) is preferable It is 2.0 mass % or more, More preferably, it is 5.0 mass % or more. It is easy to suppress a phase difference as it is more than the said lower limit. Likewise, it is preferably at most 40% by mass, more preferably at most 30% by mass. If it is below the said upper limit, since the introduction rate of other useful monomers can be raised, it is preferable. In addition, the content ratio of the said structural unit was calculated from the mass added at the time of the block copolymer before synthetic salt formation.

The mass average molecular weight Mw of the above-mentioned block copolymer is not particularly limited, but it is preferably 1,000 to 20,000, more preferably 2,000 to 15,000, and still more preferably 3000~12000. Here, the mass average molecular weight (Mw) can be measured in the same manner as above.

Also, regarding the total ratio of structural units derived from (meth)acrylate, in terms of dispersion stability, solvent resistance, and compatibility with photoinitiators, B in the block copolymer When the total structural units in a segment are 100% by mass, it is preferably at least 60% by mass, more preferably at least 80% by mass, further preferably at least 90% by mass. On the other hand, in terms of simultaneously satisfying dispersion stability and excellent solvent resistance, when the total structural units in the B block are taken as 100% by mass, the structural units derived from (meth)acrylate The total ratio may be 100% by mass. When the B block contains a structural unit derived from the above-mentioned carboxyl-containing monomer, the total structural units in the B block that are different from the structural unit derived from the above-mentioned carboxyl-containing monomer are set as 100% by mass, derived from The total ratio of the structural unit of (meth)acrylate may be 100 mass %.

In the block copolymer before salt formation, in terms of dispersibility and dispersion stability, when the total structural units of the block copolymer are 100% by mass, the total structural units of the B block The total content ratio is preferably from 40% by mass to 95% by mass, more preferably from 50% by mass to 90% by mass. Also, in the block copolymer before salt formation, in terms of improving the dispersibility of the colorant, when the total structural units of the block copolymer are taken as 100% by mass, the structural unit represented by the above general formula (III) The content ratio is preferably from 40% by mass to 95% by mass, more preferably from 50% by mass to 90% by mass. In addition, the content ratio of the said structural unit was calculated from the mass added at the time of the block copolymer before synthetic salt formation.

The (meth)acrylate-based copolymer comprising the structural unit represented by the above-mentioned general formula (I) is preferable in terms of good dispersibility, no precipitation of foreign matter when forming a coating film, and improved brightness and contrast. It is a copolymer with an amine value of 40 mgKOH/g-120 mgKOH/g. When the amine value is within the above-mentioned range, the temporal stability of the viscosity and heat resistance are excellent, and alkali developability and solvent resolubility are also excellent. In the present invention, regarding the amine value of the (meth)acrylate copolymer comprising the structural unit represented by the above general formula (I), the amine value is preferably 80 mgKOH/g or more, more preferably 90 mgKOH/g more than g. On the other hand, in terms of solvent resolubility, the amine value of the (meth)acrylate copolymer comprising the structural unit represented by the above general formula (I) is preferably 110 mgKOH/g or less, more preferably It is below 105 mgKOH/g. The amine value means the mg number of perchloric acid and equivalent potassium hydroxide required to neutralize the amine component contained in 1 g of the sample, and can be measured by the method defined in JIS-K7237. When measured by this method, even if the amine group forms a salt with the organic acid compound in the dispersant, the organic acid compound will usually dissociate, so the block copolymer itself used as a dispersant can be measured The amine value.

In the present invention, the method for producing the above-mentioned graft copolymer or block copolymer is not particularly limited, and can be produced by appropriately selecting a known polymerization method.

The content ratio (mole %, mass %) of each structural unit in the copolymer in the dispersant can be obtained from the amount of raw materials added at the time of manufacture, and can be analyzed using NMR (nuclear magnetic resonance, nuclear magnetic resonance) etc. device to measure. Moreover, the structure of a dispersing agent can be measured using NMR, various mass spectrometry, etc. Also, for the decomposed product obtained by decomposing the dispersant by thermal decomposition or the like as needed, high performance liquid chromatography, gas chromatography mass spectrometry, NMR, elemental analysis, XPS/ESCA (X-ray It can be obtained by photoelectron spectroscopy/Electron Spectroscopy for Chemical Analysis, X-ray photoelectron spectroscopy/electron spectroscopy for chemical analysis) and TOF-SIMS (time of flight secondary ion mass spectrometry, time of flight secondary ion mass spectrometry).

In the photosensitive colored resin composition of the present invention, the content of the dispersant is not particularly limited as long as it is selected so that the dispersibility and dispersion stability of the colorant are excellent. The total amount of the material components is, for example, preferably within a range of 2% by mass to 30% by mass, more preferably within a range of 3% by mass to 25% by mass. When it is more than the said lower limit, the dispersibility and dispersion stability of a coloring material are excellent, and the storage stability of a photosensitive colored resin composition is further excellent. Moreover, developability will become favorable as it is below the said upper limit. Especially in the case of forming a cured film with a high concentration of colorant, the content of the dispersant is, for example, preferably 2% by mass to 25% by mass, more preferably Within the range of 3% by mass to 20% by mass.

[Pigment Derivatives] In the case of dispersing the colorant in the photosensitive colored resin composition of the present invention, in terms of the dispersibility of the colorant and the dispersion stability of the colorant, functionalization of the pigment skeleton may be further included. Based pigment derivatives. As a functional group of a dye derivative, a basic group, an acidic group, the phthalimide methyl group which may have a substituent, etc. are mentioned, for example. The dye derivative may be a dye derivative having an acidic group, or may be a dye derivative having a sulfonic acid group (—SO ₃ H). Alternatively, it may be a metal salt or an amine salt of the above-mentioned pigment derivative having a sulfonic acid group.

Among the pigment derivatives with sulfonic acid group, the sulfonic acid group can be directly bonded to the pigment skeleton, for example, -SO ₂ NH-(CH ₂ ) _m -SO where the sulfonic acid group is bonded to the pigment skeleton through a linking group ₃ H (here, m is an integer of 1 to 6), etc. The sulfonic acid group can be directly bonded to the dye skeleton in terms of easy action on the target component. In addition, in the pigment derivatives having a sulfonic acid group, the number of substitutions of the sulfonic acid group in one molecule may be 1 to 4, preferably 1 to 2, and among them, 1 is preferable in terms of difficulty in lowering the brightness. .

The pigment skeleton of the pigment derivative used in the present invention can be appropriately selected, but in terms of the interaction with the above-mentioned diketopyrrolopyrrole pigment, R202, R122 used as the color material, or the aspect of the hue, for example Citing the quinophthalone skeleton, 𠮿 Skeleton, coumarin skeleton, naphthol azo skeleton, diketopyrrolopyrrole skeleton, quinacridone skeleton, etc. may be quinophthalone skeleton or diketopyrrolopyrrole skeleton.

Examples of pigments having a quinophthalone skeleton include quinophthalone pigments such as C.I. Pigment Yellow 138, quinophthalone dyes such as C.I. Disperse Yellow 54, 64, 67, 134, 149, 160, and C.I. Solvent Yellow 114 and 157 . The pigment having a quinophthalone skeleton is preferably C.I. Pigment Yellow 138 or Pigment Yellow 231 in terms of high transmittance and high brightness, and C.I. Pigment Yellow 138 may be used. Examples of dyes having a diketopyrrolopyrrole skeleton include C.I. Pigment Red 254, 255, 264, and 272, and C.I. Pigment Red 254 and 272 are preferable in terms of high transmittance.

The pigment derivative used in the present invention may be a pigment derivative having a quinophthalone skeleton having one sulfonic acid group, or a diketopyrrolopyrrole derivative having good dispersibility and reducing retardation. The pigment derivative of the skeleton can be a monosulfonic acid derivative of C.I. Pigment Yellow 138, a monosulfonic acid derivative of C.I. Pigment Yellow 231, or a monosulfonic acid derivative of C.I. Pigment Red 254, which can be a monosulfonic acid derivative of C.I. Sulfonic acid derivatives.

As the pigment derivative, one type may be used alone, or two or more types may be used in combination. In the photosensitive colored resin composition of the present invention, with respect to the total solid content of the photosensitive colored resin composition, the content of the pigment derivative may be, for example, 0.03% by mass to 9.75% by mass, may be 0.12% by mass to 9.0% by mass, preferably within a range of 1.0% by mass to 5.0% by mass, more preferably 2.5% by mass to 3.5% by mass.

[optional ingredients added] In the photosensitive colored resin composition, various additives may be included as needed. Examples of additives include antioxidants, polymerization terminators, chain transfer agents, leveling agents, plasticizers, surfactants, defoamers, silane coupling agents, ultraviolet absorbers, adhesion promoters, and the like. As a specific example of a surfactant and a plasticizer, what was described in Unexamined-Japanese-Patent No. 2013-029832 is mentioned, for example.

The photosensitive colored resin composition of this invention may further contain an antioxidant from the point which suppresses a line width shift amount. The antioxidant used in the present invention is not particularly limited, and may be appropriately selected from previously known ones. Specific examples of antioxidants include hindered phenol-based antioxidants, amine-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and hydrazine-based antioxidants. Fine lines can be formed in accordance with the design of the mask line width. It is preferable to use a hindered phenolic antioxidant in terms of improving the ability of patterning and in terms of heat resistance. It can also be a potential antioxidant as described in International Publication No. 2014/021023.

As hindered phenolic antioxidants, for example, pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: IRGANOX1010, manufactured by BASF Corporation), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate (trade name: Irganox 3114, manufactured by BASF), 2,4,6-tris(4- Hydroxy-3,5-di-tert-butylbenzyl) mesitylene (trade name: Irganox 1330, manufactured by BASF), 2,2'-methylenebis(6-tert-butyl-4-methyl phenol) (trade name: Sumilizer MDP-S, manufactured by Sumitomo Chemical), 6,6'-thiobis(2-tert-butyl-4-methylphenol) (trade name: Irganox 1081, manufactured by BASF), 3 , 5-di-tert-butyl-4-hydroxybenzylphosphonic acid diethyl ester (trade name: Irgamod 195, manufactured by BASF) and the like. Among them, in terms of heat resistance and light resistance, pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: IRGANOX1010, BASF manufactured by the company).

The content of the antioxidant is preferably within a range of 0.1% by mass to 10.0% by mass, more preferably 0.5% by mass to 5.0% by mass relative to the total solid content of the photosensitive colored resin composition. When it is more than the said lower limit, the ability to form a thin line pattern according to the design of a mask line width improves, and it is excellent in heat resistance. On the other hand, if it is below the said upper limit, the photosensitive colored resin composition of this invention can be made into the highly sensitive photosensitive resin composition.

<Manufacturing method of photosensitive colored resin composition> The production method of the photosensitive colored resin composition of the present invention can be prepared by the following method: colorant, alkali-soluble resin, photopolymerizable compound, photoinitiator, solvent, and various additive components used as needed, Mixing is performed using known mixing mechanisms. As the preparation method of the resin composition, for example, the following methods can be cited: (1) First, add a colorant and a dispersant to a solvent to prepare a colorant dispersion, and mix an alkali-soluble resin, a photosensitive resin, and a dispersant into the dispersion. Polymerizable compound, photoinitiator, and various additive components used as needed; Various additive components are mixed; (3) Alkali-soluble resin, photopolymerizable compound, photoinitiator, and various additive components used if necessary are added to the solvent, and after mixing, coloring materials are added and dispersed; (4) Add a colorant, a dispersant, and an alkali-soluble resin to a solvent to prepare a colorant dispersion, and then add an alkali-soluble resin, a solvent, a photopolymerizable compound, a photoinitiator, and if necessary, to the dispersion. Various additives used and mixed. Among these methods, the above-mentioned methods (1) and (4) are preferable in terms of effectively preventing the aggregation of the colorant and dispersing it uniformly.

Examples of dispersing machines for dispersing treatment include roll mills such as two-roll mills and three-roll mills, ball mills such as ball mills and vibration ball mills, paint conditioners, continuous disc bead mills, and continuous ring bead mills. Mill and other bead mills. As a preferable dispersion condition of the bead mill, the diameter of the beads used is preferably not less than 0.03 mm and not more than 2.00 mm, more preferably not less than 0.10 mm and not more than 1.0 mm.

II. Color filter The color filter of the present invention includes at least a substrate and a colored layer provided on the substrate, and at least one of the colored layers is a cured product of the photosensitive colored resin composition of the present invention.

Such a color filter of the present invention will be described with reference to the drawings. Fig. 1 is a schematic sectional view showing an example of the color filter of the present invention. According to FIG. 1 , a color filter 10 of the present invention has a substrate 1 , a light shielding portion 2 , and a colored layer 3 .

(shading layer) At least one of the colored layers used in the color filter of the present invention is a cured product of the above-mentioned photosensitive colored resin composition of the present invention. The colored layer is usually formed in the opening of the light-shielding portion on the substrate described below, and usually includes colored patterns of three or more colors. Also, the arrangement of the colored layers is not particularly limited, and general arrangements such as a stripe type, a mosaic type, a triangle type, and a 4-pixel arrangement type can be used, for example. In addition, the width, area, etc. of the colored layer can be set arbitrarily. The thickness of the colored layer can be properly controlled by adjusting the coating method, solid content concentration or viscosity of the photosensitive colored resin composition, etc., and is usually preferably in the range of 1 μm to 5 μm.

The said colored layer can be formed by the following method, for example. First, the above-mentioned photosensitive colored resin composition of the present invention is coated using a coating method such as spray coating, dip coating, bar coating, roll coating, spin coating, or die coating. Spread on the following substrates to form a wet coating film. Among them, the spin coating method and the die coating method can be preferably used. Next, the wet coating film is heated and dried using a hot plate or an oven, and then exposed through a mask of a predetermined pattern to allow photopolymerization of an alkali-soluble resin and a photopolymerizable compound. into a hardened coating. As a light source used for exposure, ultraviolet rays, such as a low pressure mercury lamp, a high pressure mercury lamp, and a metal halide lamp, an electron beam, etc. are mentioned, for example. The exposure amount is properly adjusted according to the light source used or the thickness of the coating film. In addition, heat treatment may be performed after exposure to promote polymerization reaction. The heating conditions are appropriately selected according to the compounding ratio of each component in the photosensitive colored resin composition to be used, the thickness of the coating film, and the like.

Next, a developing treatment is performed using a developing solution to dissolve and remove unexposed portions, whereby a coating film is formed in a desired pattern. As a developer, a solution obtained by dissolving an alkali in water or a water-soluble solvent is generally used. A suitable amount of surfactant and the like may also be added to the alkaline solution. Also, as a developing method, a general method can be used. After the development treatment, washing of the developing solution and drying of the cured coating film of the photosensitive colored resin composition are usually carried out to form a colored layer. In addition, heat processing may be performed after image development processing so that a coating film may fully harden. The heating conditions are not particularly limited, and may be appropriately selected according to the application of the coating film. The colored layer may be a colored layer of a fine pattern with a line width of 40 μm or less, or a colored layer of a fine pattern with a line width of 20 μm or less.

(shading part) The light-shielding portion in the color filter of the present invention is formed in a pattern on the substrate described below, and may be the same as that used as a light-shielding portion in a general color filter. It does not specifically limit as a pattern shape of the said light-shielding part, For example, shapes, such as a stripe shape and a matrix shape, are mentioned. The light-shielding portion can be a metal film such as chromium formed by sputtering, vacuum evaporation, or the like. Alternatively, the light-shielding portion may be a resin layer containing light-shielding particles such as carbon fine particles, metal oxides, inorganic pigments, and organic pigments in a resin binder. In the case of a resin layer containing light-shielding particles, there are a method of patterning by development using a photosensitive resist, a method of patterning using an inkjet ink containing light-shielding particles, and a method of performing patterning on a photosensitive resist. The method of thermal transfer, etc.

The film thickness of the light-shielding part is set to approximately 0.2 μm to 0.4 μm in the case of a metal thin film, and approximately 0.5 μm to 2 μm in the case of a black pigment dispersed or dissolved in a binder resin. .

(substrate) As the substrate, the following transparent substrates, silicon substrates, and those in which aluminum, silver, silver/copper/palladium alloy thin films, etc. are formed on transparent substrates or silicon substrates can be used. Other color filter layers, resin layers, TFT (thin-film transistor, thin-film transistor) and other transistors, circuits, etc. can also be formed on these substrates.

The transparent substrate in the color filter of the present invention is not particularly limited as long as it is transparent to visible light, and transparent substrates used in general color filters can be used. Specifically, non-flexible transparent rigid materials such as quartz glass, non-alkali glass, and synthetic quartz plates, or flexible transparent soft materials such as transparent resin films, optical resin plates, and soft glass, can be mentioned. The thickness of the transparent substrate is not particularly limited, and depending on the application of the color filter of the present invention, for example, a thickness of about 100 μm to 1 mm can be used. Moreover, the color filter of the present invention may also be formed with, for example, an overcoat layer or a transparent electrode layer, an alignment film or alignment protrusion, and a columnar spacer, in addition to the above-mentioned substrate, light-shielding portion, and colored layer.

III. Display device A display device of the present invention is characterized by having the above-mentioned color filter of the present invention. In the present invention, the configuration of the display device is not particularly limited, and may be appropriately selected from previously known display devices, for example, a liquid crystal display device or an organic light-emitting display device.

[Liquid crystal display device] A liquid crystal display device of the present invention includes the above-mentioned color filter of the present invention, a counter substrate, and a liquid crystal layer formed between the color filter and the counter substrate. Such a liquid crystal display device of the present invention will be described with reference to the drawings. Fig. 2 is a schematic diagram showing an example of a liquid crystal display device of the present invention. As shown in FIG. 2, the liquid crystal display device 40 of the present invention has a color filter 10, a counter substrate 20 having a TFT array substrate, etc., and a liquid crystal formed between the color filter 10 and the counter substrate 20. Layer 30. Furthermore, the liquid crystal display device of the present invention is not limited to the structure shown in FIG. 2, and a known structure can be adopted as a liquid crystal display device generally using a color filter.

The driving method of the liquid crystal display device of the present invention is not particularly limited, and a driving method generally used for liquid crystal display devices can be used. As such a driving method, for example, a TN (Twisted Nematic, twisted nematic) method, an IPS (in-plane switching, in-plane switching) method, an OCB (optically compensated bend, optically compensated bend) method, and an MVA (Multi -Domain Vertical Alignment, multi-domain vertical alignment) method, etc. In the present invention, any one of them is suitably used. In addition, as a counter substrate, it can be appropriately selected and used according to the driving method of the liquid crystal display device of the present invention, and the like. Furthermore, as the liquid crystal constituting the liquid crystal layer, various liquid crystals having different dielectric anisotropy and mixtures thereof can be used depending on the driving method of the liquid crystal display device of the present invention and the like.

As a formation method of a liquid crystal layer, the method generally used as the manufacturing method of a liquid crystal cell can be used, For example, a vacuum injection method, a liquid crystal dropping method, etc. are mentioned. After the liquid crystal layer is formed by the above method, the liquid crystal cell is slowly cooled to room temperature, thereby aligning the sealed liquid crystal.

[Organic Light Emitting Display Device] The organic light-emitting display device of the present invention has the above-mentioned color filter of the present invention and an organic luminescent body. The organic light emitting display device of the present invention will be described with reference to the drawings. FIG. 3 is a schematic diagram showing an example of an organic light emitting display device of the present invention. As shown in FIG. 3 , the organic light emitting display device 100 of the present invention has a color filter 10 and an organic light emitting body 80 . An organic protective layer 50 and an inorganic oxide film 60 may also be provided between the color filter 10 and the organic light emitting body 80 .

As a lamination method of the organic luminescent body 80, for example, on the upper surface of the color filter, a transparent anode 71, a hole injection layer 72, a hole transport layer 73, a light emitting layer 74, an electron injection layer 75, and the method of cathode 76; or the method of attaching the organic luminescent body 80 formed on other substrates to the inorganic oxide film 60; etc. The transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light emitting layer 74, the electron injection layer 75, and the cathode 76 in the organic luminescent body 80 can be appropriately used as known components. The organic light-emitting display device 100 manufactured in this way can be applied to, for example, a passive-driven organic EL display or an active-driven organic EL display. Furthermore, the organic light emitting display device of the present invention is not limited to the structure shown in FIG. 3 , and a known structure can be adopted as an organic light emitting display device using a color filter in general. [Example]

Hereinafter, the present invention will be specifically described with reference to examples. The present invention is not limited by these descriptions. The acid value was calculated|required by the method based on the method described in JISK0070:1992. The mass average molecular weight (Mw) was calculated|required as the standard polystyrene conversion value by GPC (gel permeation chromatography) according to the measuring method described in the said specification of this invention.

(Preparation Example 1: Preparation of Alkali-Soluble Resin A) A mixture of 40 parts by mass of benzyl methacrylate (BzMA), 15 parts by mass of methyl methacrylate (MMA), 25 parts by mass of methacrylic acid (MAA), and 3 parts by mass of azoisobutyronitrile (AIBN) , was dripped at 100° C. over 3 hours under a nitrogen stream into a polymerization tank charged with 150 parts by mass of propylene glycol monomethyl ether acetate (PGMEA). After completion|finish of dripping, it heated at 100 degreeC for 3 hours further, and obtained the polymer solution. The mass average molecular weight of the polymer solution was 7000. Next, 20 parts by mass of glycidyl methacrylate (GMA), 0.2 parts by mass of triethylamine, and 0.05 parts by mass of p-methoxyphenol were added to the obtained polymer solution, and heated at 110° C. for 10 hours, thereby Carboxylic acid group of main chain methacrylic acid and epoxy group of glycidyl methacrylate react to obtain alkali-soluble resin A solution. During the reaction, air was blown into the reaction solution in order to prevent polymerization of glycidyl methacrylate. Furthermore, the reaction was followed by measuring the acid value of the solution. The obtained alkali-soluble resin A solution is a resin obtained by using GMA to introduce a side chain having an ethylenically unsaturated bond into the main chain formed by the copolymerization of BzMA, MMA, and MAA. The solid content is 40% by mass, and the acid value is 74 mgKOH/g, ethylenically unsaturated bond equivalent 711, mass average molecular weight 12000.

(Preparation Example 2: Preparation of Compound IA) (1) Synthesis of Intermediate IA1 Put 0.2 mol of diphenyl sulfide, 0.22 mol of crushed AlCl ₃ , and 150 ml of dichloroethane into a 500 ml four-neck flask and Stir, flow in argon, and cool with an ice bath. When the temperature drops to 0°C, start to drop a solution containing 0.22 mol of cyclohexylpropionyl chloride and 42 g of dichloroethane, while adjusting the temperature to below 10°C The addition took about 1.5 hours on one side. After raising the temperature to 15° C. and continuing to stir for 2 hours, the reaction liquid was discharged. Slowly pour the reaction solution into dilute hydrochloric acid prepared with 400 g of ice and 65 ml of concentrated hydrochloric acid under stirring, use a separatory funnel to separate the lower layer, and use 50 ml of dichloroethane to extract the upper layer. The extract is combined with the lower layer. Then, wash with a NaHCO ₃ solution prepared with 10 g of NaHCO ₃ and 200 g of water, wash with 200 ml of water three times until the pH becomes neutral, and remove by drying with 60 g of anhydrous MgSO ₄ After removing the water, the dichloroethane was evaporated by rotary evaporation. The solid powder remaining in the rotary evaporating flask was put into 200 ml of petroleum ether, suction-filtered, and then put into 150 ml of absolute ethanol for heating and reflux. Thereafter, it was cooled to room temperature, furthermore cooled with ice for 2 hours, and then dried in a 50° C. oven for 2 hours after suction filtration to obtain the following intermediate IA1.

[Chem. 10] Intermediate IA1

(2) Synthesis of intermediate IA2 Put 42 g of the above-mentioned intermediate IA1, 400 g of tetrahydrofuran, 200 g of concentrated hydrochloric acid, and 24.2 g of isoamyl nitrite into a 500 ml four-necked flask, and stir at room temperature for 5 hours. Drain the reaction solution. The reaction solution was put into a large beaker, 1000 ml of water was added and stirred, and the layers were separated by standing overnight to obtain a yellow viscous liquid. Use dichloroethane to extract the viscous liquid, add 50 g of anhydrous MgSO ₄ to make it dry, then carry out suction filtration, and remove the solvent by rotating the filtrate to obtain an oily viscous product. Then, the viscous material was put into 150 ml of petroleum ether, stirred, precipitated, and suction filtered to obtain a white powdery solid. Then, it dried at 60 degreeC for 5 hours, and obtained the following intermediate product IA2.

[Chem. 11] Intermediate IA2

(3) Synthesis of Compound IA 34 g of the above-mentioned intermediate IA2, 350 ml of dichloroethane, and 12.7 g of triethylamine were put into a 1000 ml four-neck flask and stirred, cooled in an ice bath, and the temperature was lowered to 0 The dropwise addition of a solution containing 15.7 g of acetyl chloride and 15 g of dichloroethane was started at °C, and the addition took about 1.5 hours. After continuing to stir for 1 hour, 500 ml of cold water was added dropwise, and layers were separated using a separatory funnel. Wash once with 200 ml of 5% NaHCO ₃ solution, then wash twice with 200 ml of water until the pH value becomes neutral, then wash once with dilute hydrochloric acid mixed with 20 g of concentrated hydrochloric acid and 400 ml of water, and then wash with After washing with 200 ml of water for 3 times, it was dried with 100 g of anhydrous MgSO ₄ , and the solvent was removed by rotary evaporation to obtain a viscous liquid. An appropriate amount of methanol was added to the viscous liquid to precipitate a white solid, which was filtered and dried to obtain the following compound IA. In addition, the molecular weight of the following compound IA was 395.51.

[Chem. 12] Compound IA

(Preparation Example 3: Preparation of Y138 Sulfonic Acid Derivatives) While cooling 374.76 parts by mass of 11 mass % oleum to 10° C. while stirring, 74.96 parts by mass of C.I. Pigment Yellow 138 was added. Then, it stirred at 90 degreeC for 6 hours. The reaction liquid was added to 1600 parts by mass of ice water and stirred for 15 minutes, and then the precipitate was filtered. The obtained wet filter cake was washed 3 times with 800 ml of water. The wet cake was vacuum-dried at 80° C. to obtain 81.55 parts by mass of a yellow product. The mass analysis result obtained by TOF-MS (Time Of Flight Mass Spectrometry) of the yellow product (Y138 sulfonic acid derivative), and the molecular weight of the Y138 monosulfonic acid derivative with the following structure ( Mw=774.0) agrees.

[chemical 13]

(Preparation Example 4: Preparation of Dispersant 1 (Basic Block Copolymer 1)) A 500 ml four-necked separable flask was decompressed and dried, and then replaced with Ar (argon gas). While flowing Ar, add 100 g of dehydrated THF, 2.0 g of methyltrimethylsilyl dimethylketene acetal, and 0.15 ml of a 1 M acetonitrile solution of tetrabutylammonium-3-chlorobenzoate (TBACB) , mesitylene 0.2 g. Using a dropping funnel, 7.8 parts by mass of n-butyl methacrylate (BMA), 48.9 parts by mass of methyl methacrylate (MMA), and diethylene glycol monobutyl ether methacrylate (commercial product Name: Lightester BC, Kyoeisha Chemical Co., Ltd.) 25.7 parts by mass. Since heat was generated during the reaction, it was cooled in an ice bath to keep the temperature below 40°C. After 1 hour, 17.6 parts by mass of dimethylaminoethyl methacrylate (DMMA) was added dropwise over 15 minutes. After reacting for 1 hour, 5 g of methanol was added to stop the reaction. The solvent was removed under reduced pressure to obtain a basic block copolymer 1 . The mass average molecular weight determined by GPC measurement (NMP LiBr10 mM) was 8,000, and the amine value was 70 mgKOH/g.

(Preparation Example 5: Preparation of Dispersant 2 (Basic Block Copolymer 2)) In Preparation Example 4, 9.8 parts by mass of n-butyl methacrylate (BMA), 62.6 parts by mass of methyl methacrylate (MMA), and methoxypolyethylene glycol monomethacrylate (polyethylene glycol Chain repeat number n≒23, trade name Blemmer PME-1000, manufactured by NOF) 6.6 parts by mass instead of 7.8 parts by mass of n-butyl methacrylate (BMA), 48.9 parts by mass of methyl methacrylate (MMA), and 25.7 parts by mass of diethylene glycol monobutyl ether methacrylate (trade name: Lightester BC, Kyoeisha Chemical Co., Ltd.), and 21.0 parts by mass of dimethylaminoethyl methacrylate (DMMA). Except that, it carried out similarly to the preparation example 4, and obtained the basic block copolymer 2. The mass average molecular weight determined by GPC measurement (NMP LiBr10 mM) was 7,800, and the amine value was 70 mgKOH/g.

(Preparation Example 6: Preparation of Dispersant 3 (Basic Graft Copolymer 3)) (1) Synthesis of macromonomer A Add 70.0 parts by mass of propylene glycol methyl ether acetate (PGMEA) to a reactor equipped with a condenser, a funnel for addition, an inlet for nitrogen, a mechanical stirrer, and a digital thermometer, and heat to a temperature of 90 while stirring under a nitrogen stream. ℃. Add 6.0 parts by mass of methoxypolyethylene glycol monomethacrylate (repetition number of polyethylene glycol chain n≒23, trade name Blemmer PME-1000, manufactured by NOF) dropwise over 1.5 hours, methoxypolyethylene glycol Diol monomethacrylate (number of repetitions of polyethylene glycol chain n≒4, trade name Blemmer PME-200, manufactured by NOF) 41.0 parts by mass, methyl methacrylate (MMA) 53.0 parts by mass, mercaptoethanol 4.0 A mixed solution of parts by mass, 30 parts by mass of PGMEA, and 1.0 parts by mass of α,α'-azobisisobutyronitrile (AIBN) was further reacted for 3 hours. Then, the nitrogen flow was stopped, and the reaction solution was cooled to 80° C., 8.74 parts by mass of Karenz MOI (manufactured by Showa Denko Co., Ltd.), 0.125 g of dioctyltin dilaurate, 0.125 parts by mass of p-methoxyphenol, and 30 parts by mass of PGMEA and stirred for 3 hours to obtain a 50% solution of macromonomer A. By means of GPC (gel permeation chromatography), the obtained macromonomer A was confirmed under the conditions of N-methylpyrrolidone and 0.01 mol/L lithium bromide/polystyrene standard, and the result was Mass average molecular weight (Mw) 4700, molecular weight distribution (Mw/Mn) 1.6. (2) Synthesis of basic graft copolymer 3 Add 63.1 parts by mass of PGMEA to a reactor equipped with a condenser, an addition funnel, an inlet for nitrogen, a mechanical stirrer, and a digital thermometer, and heat to a temperature of 85° C. while stirring under a nitrogen stream. 165.4 parts by mass of the 50% solution of the above-mentioned macromonomer A (effective solid content 82.7 parts by mass), 17.3 parts by mass of 2-(dimethylamino)ethyl methacrylate (DMMA), and A mixed solution of 1.24 parts by mass of alkanethiol, 49.4 parts by mass of PGMEA, and 1.0 parts by mass of AIBN was heated and stirred for 3 hours, then a mixed solution of 0.10 parts by mass of AIBN and 6.0 parts by mass of PGMEA was added dropwise over 10 minutes, and then at the current temperature The aging was carried out for 1 hour under , whereby a 35.0% by mass solution of graft copolymer 3 was obtained. The GPC measurement result of the obtained basic graft copolymer 3 was a mass average molecular weight (Mw) of 16,000. In addition, the amine value was 105 mgKOH/g.

(Preparation Example 7: Preparation of Dispersant 4 (Basic Block Copolymer 4)) In Preparation Example 4, 13.4 parts by mass of n-butyl methacrylate (BMA), 47.5 parts by mass of methyl methacrylate (MMA), 7.5 parts by mass of benzyl methacrylate (BzMA), and 2- Ethylhexyl ester (EHMA) 9.0 mass parts replaces n-butyl methacrylate (BMA) 7.8 mass parts, methyl methacrylate (MMA) 48.9 mass parts, and diethylene glycol monobutyl ether methacrylate ( Trade name: Lightester BC, Kyoeisha Chemical Co., Ltd.) 25.7 parts by mass, and 22.6 parts by mass of dimethylaminoethyl methacrylate (DMMA), except that, the base was obtained in the same manner as in Preparation Example 4 Sexual block copolymer 4. The mass average molecular weight obtained by GPC measurement (NMP LiBr 10 mM) was 7,000, and the amine value was 90 mgKOH/g.

(Manufacturing Example 1: Manufacture of Pigment Dispersion Liquid R-1) 12.4 parts by mass of the colorant (C.I. Pigment Red 202), 10.8 parts by mass of the PGMEA solution (solid content 60 mass %) of the basic block copolymer 1 obtained in Preparation Example 4 as a dispersant, Y138 sulfonic acid derivative Put 0.7 parts by mass of the product, 9.8 parts by mass of the alkali-soluble resin A obtained in Preparation Example 1, 66.4 parts by mass of PGMEA, and 100 parts by mass of zirconia beads with a particle diameter of 2.0 mm into a mayonnaise bottle, and use a paint shaker (Asada Iron Co., Ltd. (manufactured by Industrial Co., Ltd.) shake for 1 hour as pre-crushing, then take out zirconia beads with a particle size of 2.0 mm, add 200 parts by mass of zirconia beads with a particle size of 0.1 mm, and disperse for 8 hours with a paint shaker in the same way as the formal crushing , so as to obtain the colorant dispersion R-1.

(Manufacturing Examples 2-5: Manufacture of Pigment Dispersion Liquids R-2-R-5) In Production Example 1, C.I. Pigment Red 122, C.I. Pigment Red 254, C.I. Pigment Red 291, or C.I. Pigment Red 177 were used instead of C.I. Pigment Red 202 as a coloring material, except that it was performed in the same manner as in Production Example 1. Color material dispersion liquids R-2 to R-5 were produced.

(Manufacturing Example 6: Manufacture of Pigment Dispersion Liquid R-6) In Production Example 1, 16.3 parts by mass of the PGMEA solution (solid content 40% by mass) of the basic block copolymer 2 obtained in Preparation Example 5 was used instead of the basic block copolymer obtained in Preparation Example 4 10.8 mass parts of PGMEA solution (60 mass % of solid content), except having used 61.0 mass parts of PGMEA instead of PGMEA 66.4 mass parts, it operated similarly to manufacture example 1, and obtained the color material dispersion liquid R-6.

(Manufacturing Examples 7-9: Manufacture of Pigment Dispersion Liquids R-7-R-9) In Production Example 6, C.I. Pigment Red 122, C.I. Pigment Red 254, or C.I. Pigment Red 291 were used instead of C.I. Pigment Red 202 as a colorant, except that, the same operation as Production Example 6 was performed to produce a colorant dispersion R-7～R-9.

(Manufacturing Example 10: Manufacture of Pigment Dispersion Liquid R-10) In Production Example 1, 18.6 parts by mass of the PGMEA solution (solid content 35% by mass) of the basic graft copolymer 3 obtained in Preparation Example 6 was used instead of the basic block copolymer obtained in Preparation Example 4 1 PGMEA solution (solid content 60 mass%) 10.8 mass parts, except having used PGMEA 58.7 mass parts instead of PGMEA 66.4 mass parts, it operated similarly to manufacture example 1, and obtained the color material dispersion liquid R-10.

(Manufacturing Examples 11-13: Manufacture of Pigment Dispersion Liquid R-11-R-13) In Production Example 10, C.I. Pigment Red 122, C.I. Pigment Red 254, or C.I. Pigment Red 291 were used instead of C.I. Pigment Red 202 as a coloring material, and the coloring material dispersion was produced in the same manner as in Production Example 10 except that R-11 to R-13.

(Manufacturing Example 14: Manufacture of Pigment Dispersion Liquid R-14) In Production Example 1, 13.0 parts by mass of the PGMEA solution (solid content 50% by mass) of the basic block copolymer 4 obtained in Preparation Example 7 was used instead of the basic block copolymer obtained in Preparation Example 4 1 PGMEA solution (solid content 60 mass%) 10.8 mass parts, except having used PGMEA 64.3 mass parts instead of PGMEA 66.4 mass parts, it operated similarly to manufacture example 1, and obtained the color material dispersion liquid R-14.

(Manufacturing Examples 15-17: Manufacture of Colorant Dispersion Liquid R-15-R-17) In Production Example 14, C.I. Pigment Red 122, C.I. Pigment Red 254, or C.I. Pigment Red 291 were used instead of C.I. Pigment Red 202 as a coloring material, and the coloring material dispersion was produced in the same manner as in Production Example 14 except that R-15 to R-17.

(Example 1: Manufacture of Photosensitive Colored Resin Composition 1) Each colorant dispersion was added in the mass parts recorded in Table 1, and 4.6 mass parts of alkali-soluble resin A of Preparation Example 1, M-403 (trade name ARONIX M-403, Dongya Synthetic ( Co., Ltd., unsaturated bond equivalent of 98.8 to 99.6) 2.8 parts by mass, 0.2 parts by mass of Compound IA of Preparation Example 2 as a photoinitiator, leveling agent (trade name MEGAFAC R-08MH, manufactured by DIC Co., Ltd.) 0.30 mass parts, PGMEA 48.6 mass parts, and the photosensitive colored resin composition 1 was obtained.

(Examples 2-20: Production of Photosensitive Colored Resin Compositions 2-20) In Example 1, each colorant dispersion liquid, the alkali-soluble resin A of Preparation Example 1, M-403 as a photopolymerizable compound, and PGMEA were changed to the mass parts recorded in Table 1 or Table 2 to obtain photosensitive Permanent coloring resin composition 2-20.

(Comparative Examples 1-8: Production of Comparative Photosensitive Colored Resin Compositions C1-C8) In Example 1, each colorant dispersion liquid, the alkali-soluble resin A of Preparation Example 1, M-403 as a photopolymerizable compound, and PGMEA were changed to the mass parts recorded in Table 3 to obtain comparative photosensitive coloring Resin compositions C1 to C8.

[Table 1] Table 1 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Photosensitive colored resin composition 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Pigment ratio (wt%) R202 9.2 18.7 34.5 4.7 15.5 15.5 13.6 9.2 18.7 34.5 4.7 15.5 15.5 13.6 R122 0.3 0.5 0.6 0.2 0.0 0.0 0.4 0.3 0.5 0.6 0.2 0.0 0.0 0.4 R254 90.5 80.8 64.8 90.5 80.8 64.8 R291 95.1 84.5 84.5 86.0 95.1 84.5 84.5 86.0 R177 total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Pigment dispersion (mass parts) R-1 3.6 7.2 13.9 1.9 5.693 6.327 5.6 R-2 0.1 0.2 0.2 0.1 0.001 0.006 0.2 R-3 35.1 31.0 26.2 R-4 39.7 34.6 34.500 35.5 R-5 R-6 3.6 7.2 13.9 1.9 5.7 6.3 5.6 R-7 0.1 0.2 0.2 0.1 0.0 0.0 0.2 R-8 35.1 31.0 26.2 R-9 39.7 34.6 34.5 35.5 Alkali soluble resin 5.6 5.7 5.2 4.9 5.2 5.1 5.0 5.6 5.7 5.2 4.9 5.2 5.1 5.0 M-403 3.3 3.4 3.1 3 3.1 3.1 3.0 3.3 3.4 3.1 3 3.1 3.1 3.0 PGMEA 51.4 51.7 50.5 49.5 50.5 50.1 49.8 51.4 51.7 50.5 49.5 50.5 50.1 49.8

[Table 2] Table 2 Example 15 Example 16 Example 17 Example 18 Example 19 Example 20 Photosensitive colored resin composition 15 16 17 18 19 20 Pigment ratio (wt%) R202 9.2 18.7 34.5 4.7 9.2 4.7 R122 0.3 0.5 0.6 0.2 0.3 0.2 R254 90.5 80.8 64.8 90.5 R291 95.1 95.1 R177 total 100.0 100.0 100.0 100.0 100.0 100.0 Pigment dispersion (mass parts) R-10 3.6 7.2 13.9 1.9 R-11 0.1 0.2 0.2 0.1 R-12 35.1 31.0 26.2 R-13 39.7 R-14 3.6 1.9 R-15 0.1 0.1 R-16 35.1 R-17 39.7 Alkali soluble resin 5.6 5.7 5.2 4.9 5.7 5.2 M-403 3.3 3.4 3.1 3 3.4 3.1 PGMEA 51.4 51.7 50.5 49.5 51.7 50.4

[Table 3] Table 3 Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative Example 5 Comparative example 6 Comparative Example 7 Comparative Example 8 Comparison of Photosensitive Colored Resin Compositions C1 C2 C3 C4 C5 C6 C7 C8 Pigment ratio (wt%) R202 9.9 20.0 36.3 14.7 R122 R254 90.1 80.0 63.7 76.0 54.3 22.8 R291 85.3 61.5 R177 38.5 24.0 45.7 77.2 total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Pigment dispersion (mass parts) R-1 3.8 7.1 14.3 5.9 R-2 R-3 34.5 28.6 25.1 29.9 21.6 10.0 R-4 34.4 25.4 R-5 15.9 9.4 18.2 34.0 Alkali soluble resin 5.7 6.3 5.5 5.2 5.0 5.5 5.3 4.4 M-403 3.4 3.8 3.3 3.1 3.0 3.3 3.2 2.7 PGMEA 51.7 53.4 51.0 50.4 49.8 51.0 50.7 48.0

[Evaluation method] <Optical performance> The colored resin compositions of Examples and Comparative Examples were coated to a thickness of y = 0.653 (film thickness = 2.2 μm) after post-baking, respectively, using a spin coater. 0.7 mm glass substrate (manufactured by NH TECHNO GLASS Co., Ltd., "NA35"). Then, it heat-dried for 3 minutes on the hot plate of 80 degreeC. A cured film (red coloring layer) was obtained by irradiating 60 mJ/cm ² of ultraviolet rays with an ultra-high pressure mercury lamp without passing through a photomask, and then post-baking in a clean oven at 230°C for 30 minutes. Chromaticity (x, y) and brightness (Y) of the obtained colored substrate were measured using "microspectrometry apparatus OSP-SP200" manufactured by Olympus Corporation.

＜Phase difference＞ Phase difference measurement was performed using the same cured film (red colored layer) as used for optical performance evaluation. The retardation of the coloring layer is based on the retardation (Rth) in the thickness direction calculated from the following formula. Retardation (Rth) was measured using a retardation layer measurement device (AxoscanTM Mueller Matrix Polarimeter manufactured by AXOMETRICS). The measurement wavelength of the red colored layer is measured at 620 nm. Rth is an integer rounded off to the first decimal place. Rth＝((Nx＋Ny)/2－Nz)d Nx: Refractive index in the direction of the slow axis in the plane Ny: Refractive index in the direction of the fast axis in the plane Nz: Refractive index in the thickness direction d: film thickness (nm) (Phase difference evaluation standard) A: Rth is less than 10 B: Rth is 11 to 15 C: Rth is 16 or more

[Table 4] Table 4 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Pigment ratio (wt%) R202 9.2 18.7 34.5 4.7 15.528 15.503 13.6 9.2 18.7 34.5 4.7 15.528 15.503 13.6 R122 0.3 0.5 0.6 0.2 0.001 0.014 0.4 0.3 0.5 0.6 0.2 0.001 0.014 0.4 R254 90.5 80.8 64.8 90.5 80.8 64.8 R291 95.1 84.471 84.482 86.0 95.1 84.471 84.482 86.0 R177 evaluate x 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 the y 0.330 0.323 0.313 0.330 0.323 0.323 0.323 0.330 0.323 0.313 0.330 0.323 0.323 0.323 Y 20.5 18.9 16.8 20.6 19.0 19.0 18.9 20.5 18.9 16.8 20.6 19.0 19.0 18.9 phase difference A A A A B B A A A A A B B A

[Table 5] Table 5 Example 15 Example 16 Example 17 Example 18 Example 19 Example 20 Pigment ratio (wt%) R202 9.2 18.7 34.5 4.7 9.2 4.7 R122 0.3 0.5 0.6 0.2 0.3 0.2 R254 90.5 80.8 64.8 90.5 R291 95.1 95.1 R177 evaluate x 0.653 0.653 0.653 0.653 0.653 0.653 the y 0.330 0.323 0.313 0.330 0.330 0.330 Y 20.5 18.9 16.8 20.6 20.4 20.5 phase difference A A A A B B

[Table 6] Table 6 Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative Example 5 Comparative example 6 Comparative Example 7 Comparative Example 8 Pigment ratio (wt%) R202 9.9 20.0 36.3 14.7 R122 R254 90.1 80.0 63.7 76.0 54.3 22.8 R291 85.3 61.5 R177 38.5 24.0 45.7 77.2 evaluate x 0.653 0.653 0.653 0.653 0.653 0.653 0.653 0.653 the y 0.330 0.323 0.313 0.323 0.323 0.330 0.323 0.313 Y 20.5 18.9 17.1 19.0 18.7 20.3 18.6 16.6 phase difference C C C C A A A A

＜Summary of results＞ Regarding the comparative photosensitive colored resin compositions of Comparative Examples 5 to 8 in which the conventional diketopyrrolopyrrole pigment and R177 were combined, the phase difference was suppressed, but the brightness Y was insufficient for each y value. Coloring layer. With regard to the comparative photosensitive colored resin compositions of Comparative Examples 1 to 4 in which R202 was used instead of R177 as a combination of diketopyrrolopyrrole pigments, it was clear that although each value of y can increase the ratio of diketopyrrolopyrrole pigments When the ratio is included, the luminance Y increases, but the phase difference becomes higher. On the other hand, it became clear that the photosensitive colored resin compositions of Examples 1-20 were all able to form the colored layer which the brightness improved and the retardation reduced for each y value. In the examples, when the content ratio of C.I. Pigment Red 122 is a predetermined amount relative to the total content of C.I. Pigment Red 202 and C.I. Pigment Red 122, the retardation suppression effect is high. In addition, in the examples, when a dispersant of a (meth)acrylate-based copolymer having a polyethylene glycol chain is used in combination with a pigment including the above-mentioned C.I. Pigment Red 202 and C.I. Pigment Red 122, the expression The output phase difference suppression effect is high.

1: Substrate 2: shading part 3: coloring layer 10:Color filter 20: facing the substrate 30: Liquid crystal layer 40: Liquid crystal display device 50: organic protective layer 60: Inorganic oxide film 71: Transparent anode 72: Hole injection layer 73: Hole transport layer 74: luminous layer 75: Electron injection layer 76: Cathode 80: organic luminous body 100: Organic light-emitting display device

Fig. 1 is a schematic sectional view showing an example of the color filter of the present invention. Fig. 2 is a schematic cross-sectional view showing an example of a liquid crystal display device of the present invention. FIG. 3 is a schematic cross-sectional view showing an example of an organic light emitting display device of the present invention.

1: Substrate

2: shading part

3: coloring layer

10:Color filter

Claims (4)

A photosensitive colored resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, and a solvent, and The above color materials include diketopyrrolopyrrole pigments, C.I. Pigment Red 202, and C.I. Pigment Red 122. The photosensitive colored resin composition according to Claim 1, wherein the content ratio of C.I. Pigment Red 122 is 0.01% by mass to 3% by mass relative to the total content of C.I. Pigment Red 202 and C.I. Pigment Red 122. A color filter comprising at least a substrate and a colored layer disposed on the substrate, and at least one of the colored layers is a hardened photosensitive colored resin composition according to claim 1 or 2. A display device having the color filter according to claim 3.