Photosensitive coloring composition, cured product, image display panel, color filter, image display device, and method for producing the cured product

Abstract

To provide: a photosensitive coloring composition which is excellent in storage stability, is excellent in sensitivity when a pattern is formed, and enables suppression of generation of a residue and outgassing; a cured product; an image display panel; a color filter; an image display device; and a method for producing a cured product.SOLUTION: A photosensitive coloring composition is provided, which includes silsesquioxane having a structural unit (I) represented by formula (1), an alkali-soluble resin, a coloring material, a radiation-sensitive radical polymerization initiator, and an organic solvent, and in which the content of a silanol group to the total content of the structural units constituting the silsesquioxane is less than 0.3 by mole ratio. In the formula (1), X is a group having specific structure.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a photosensitive coloring composition, a cured product, an image display panel, a color filter, an image display device, and a method for producing the cured product. [Background technology]

[0002] In recent years, photolithography has become the mainstream method for producing color filters and black matrices for display devices. For example, when producing color filters using photolithography, a photosensitive composition containing a coloring material such as a dye and a polymer is applied to a substrate to form a coating film, which is then exposed to light through a photomask with a predetermined opening pattern, and then developed to dissolve and remove the unexposed portions, thereby forming a cured pattern (i.e., a colored pattern) (see, for example, Patent Document 1). After development, the coating film is usually post-baked at a temperature of 200 to 250°C for about 30 to 60 minutes to promote curing and improve the solvent resistance and hardness of the film.

[0003] In a display device using an organic electroluminescence (organic EL) element, a display area is partitioned by a partition material (also called a bank), and an organic light-emitting substance is applied between the partitions by an inkjet method or the like to form a light-emitting layer. In recent years, a photosensitive composition containing a coloring material has been used to form the partitions by a photolithography method, thereby imparting light-blocking properties to the partitions. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2-144502 Summary of the Invention [Problem to be solved by the invention]

[0005] When a photosensitive composition contains a colorant, the resolution may be poor or residues may be generated in the resulting cured product. Furthermore, when a photosensitive composition contains a colorant, photocuring is inhibited by absorption of the colorant, which tends to increase outgassing due to uncured components. Furthermore, heating a cured product formed from a photosensitive composition at a high temperature (e.g., 200°C or higher) may also generate outgassing. When the cured product is used as a partition wall material, the partition wall material is adjacent to the light-emitting layer, which can cause a problem of partially non-emitting regions (hereinafter also referred to as dark spots) due to the generated outgassing. Furthermore, photosensitive compositions are also required to not increase in viscosity or the like even when stored until actual use (i.e., to have excellent storage stability).

[0006] Therefore, an object of the present invention is to provide a photosensitive coloring composition that has excellent storage stability, excellent sensitivity during pattern formation, and can suppress the generation of residues and outgassing, a cured product, an image display panel, a color filter, an image display device, and a method for producing the cured product. [Means for solving the problem]

[0007] As a result of extensive research into solving the above problem, the present inventors have found that the above object can be achieved by employing the following configuration, and have thus completed the present invention.

[0008] In one embodiment, the present invention provides A silsesquioxane having a structural unit (I) represented by the following formula (1): Alkali-soluble resin, Color material, a radiation-sensitive radical polymerization initiator, and Contains an organic solvent, The present invention relates to a photosensitive coloring composition in which the content of silanol groups relative to the total content of structural units constituting the silsesquioxane is less than 0.3 in terms of molar ratio. [ka] (In the above formula (1), X is a group represented by the following formula (2). [ka] (In the above formula (2), R 1 are each independently a hydrogen atom or a methyl group. 2 are each independently an alkanediyl group having 2 to 10 carbon atoms.

[0009] In another embodiment, the present invention provides The present invention relates to a cured product obtained by curing the photosensitive coloring composition, an image display panel having the cured product as a color pattern of a color filter, an image display device having the image display panel, a color filter having the cured product as a black matrix, an image display panel having the color filter, an image display device having the image display panel, and an image display device having the cured product as a light-shielding partition wall material.

[0010] In another embodiment, the present invention provides A step of applying the photosensitive coloring composition onto a substrate to form a coating film; site-selectively exposing the coating to light; developing the exposed coating; heating the developed patterned coating; The present invention relates to a method for producing a patterned cured product comprising the steps of: [Effects of the Invention]

[0011] The photosensitive coloring composition of the present invention contains a silsesquioxane having a specific structure, and thus has excellent storage stability, and despite containing a colorant, has excellent sensitivity during pattern formation, and can suppress the generation of residues and outgassing in the formed cured product. [Brief explanation of the drawings]

[0012] [Figure 1] This shows a cross-sectional view of an organic EL panel with a POL-LESS structure that does not have a polarizing plate. DETAILED DESCRIPTION OF THE INVENTION

[0013] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to these embodiments.

[0014] Matters related to the embodiments will be described in detail below. In this specification, a numerical range indicated using "to" means that the numerical values ​​before and after "to" are included as the lower and upper limits.

[0015] In this specification, the term "hydrocarbon group" includes chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. The term "chain hydrocarbon group" refers to a linear hydrocarbon group or a branched hydrocarbon group that does not contain a cyclic structure in the main chain and is composed solely of a chain structure. However, the chain hydrocarbon group may be saturated or unsaturated. The term "alicyclic hydrocarbon group" refers to a hydrocarbon group that contains only an alicyclic hydrocarbon structure as a ring structure and does not contain an aromatic ring structure. However, the alicyclic hydrocarbon group does not necessarily have to be composed solely of an alicyclic hydrocarbon structure, and also includes groups that have a chain structure as part of it. The term "aromatic hydrocarbon group" refers to a hydrocarbon group that contains an aromatic ring structure as a ring structure. However, the aromatic hydrocarbon group does not necessarily have to be composed solely of an aromatic ring structure, and may contain a chain structure or an alicyclic hydrocarbon structure as part of it. The ring structures of the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a substituent consisting of a hydrocarbon structure.

[0016] In this specification, "(meth)acryloyl" is intended to encompass "acryloyl" and "methacryloyl", "(meth)acrylic" is intended to encompass "acrylic" and "methacrylic", and "(meth)acrylate" is intended to encompass "acrylate" and "methacrylate".

[0017] The curable composition of the present invention will now be described.

[0018] ≪Curable composition≫ The photosensitive coloring composition according to this embodiment (hereinafter also referred to as "the composition") is A silsesquioxane (A) having a structural unit (I) represented by the following formula (1): Alkali-soluble resin (B), Coloring material (C), a radiation-sensitive radical polymerization initiator (D), and containing an organic solvent (G), The molar ratio of the content of silanol groups to the total content of structural units constituting the silsesquioxane (A) is less than 0.3. [ka] (In the above formula (1), X is a group represented by the following formula (2). [ka] (In the above formula (2), R 1 are each independently a hydrogen atom or a methyl group. 2 are each independently an alkanediyl group having 2 to 10 carbon atoms.

[0019] Each component contained in the present composition, as well as other components that may be blended as needed, will be described below.

[0020] <Silsesquioxane (A)> The silsesquioxane (A) has a structural unit (I) represented by the following formula (1), and the content of silanol groups relative to the total content of the structural units constituting the silsesquioxane (A) is less than 0.3 in terms of molar ratio. [ka] (In the above formula (1), X is a group represented by the following formula (2). [ka] (In the above formula (2), R 1are each independently a hydrogen atom or a methyl group. 2 are each independently an alkanediyl group having 2 to 10 carbon atoms.

[0021] Silsesquioxane is a siloxane compound whose main chain skeleton consists of Si-O bonds, usually obtained by hydrolysis and condensation of trifunctional silanes, and is represented by -(RSiO 1.5 Silsesquioxanes are known as polymers having a structural unit represented by the formula: (R)-(R is a monovalent organic group). Silsesquioxanes are known to have various skeletal structures, such as a cage structure, a ladder structure, and a random structure. The silsesquioxane (A) used in the present composition may have any structure, but preferably has a cage structure or a ladder structure.

[0022] The silsesquioxane (A) may have a structural unit other than the structural unit (I).

[0023] Because the composition contains a silsesquioxane (A) having a specific structure, it has excellent storage stability, excellent sensitivity during pattern formation, and can suppress the generation of residues and outgassing in the formed cured product.

[0024] Structural Units The structural unit (I) is represented by the following formula (1). [ka] (In the above formula (1), X is a group represented by the following formula (2). [ka] (In the above formula (2), R 1 are each independently a hydrogen atom or a methyl group. 2 are each independently an alkanediyl group having 2 to 10 carbon atoms.

[0025] The above formula (1) has an average of 1.5 oxygen atoms and one X group per silicon atom, and silsesquioxane (A) is a structural unit (XSiO ) in which one X group and three oxygen atoms are bonded to one silicon atom, as represented by the following formula (i): 1.5 ) is included. [ka] (In formula (i), * represents a bond to the silicon atom of another structural unit.)

[0026] Above R 1 is a hydrogen atom or a methyl group.

[0027] Above R 2 is an alkanediyl group having 2 to 10 carbon atoms. Examples of the alkanediyl group include an ethanediyl group, a propanediyl group, a butanediyl group, a hexanediyl group, an octanediyl group, a nonanediyl group, and a decanediyl group. Some or all of the hydrogen atoms of the alkanediyl group may be substituted with a substituent such as a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom); a hydroxy group; a carboxy group; a cyano group; a nitro group; an alkyl group; an alkoxy group; an alkoxycarbonyl group; an alkoxycarbonyloxy group; an acyl group; an acyloxy group, or a group in which the hydrogen atoms of these groups are substituted with halogen atoms.

[0028] Among the above alkanediyl groups having 2 to 10 carbon atoms, alkanediyl groups having 2 to 8 carbon atoms are preferred, alkanediyl groups having 2 to 5 carbon atoms are more preferred, and propanediyl groups are even more preferred.

[0029] Specific examples of the structural unit (I) are not particularly limited, but include structures represented by the following formula: 1 is the same as the above formula (2).

[0030] [ka]

[0031] The silsesquioxane (A) may contain silanol groups (—SiOH), but the molar ratio (molar amount of silanol groups / total molar amount of structural units constituting the silsesquioxane (A)) of the silsesquioxane (A) to the total content of structural units constituting the silsesquioxane (A) is less than 0.3, preferably less than 0.25, and more preferably 0.2 or less. A molar ratio of less than 0.3 results in a high degree of condensation, and the silsesquioxane tends to have a cage structure or ladder structure. As a result, the composition has excellent storage stability and can produce a cured product (cured film) with excellent resolution, residue, and outgassing properties. The lower limit of the molar ratio is not particularly limited and may be 0, 0.01, or 0.05.

[0032] [Structural unit (II)] The silsesquioxane (A) preferably has, in addition to the structural unit (I) represented by the above formula (1), a structural unit (II) represented by the following formula (3). [ka] (In the above formula (3), Y is a monovalent organic group having a carboxy group, a carboxylic anhydride group, a phenolic hydroxyl group, or a combination thereof.)

[0033] The monovalent organic group represented by Y may be any group having a carboxy group, a carboxylic anhydride group, a phenolic hydroxyl group, or a combination thereof.

[0034] Examples of the monovalent organic group for Y include monovalent hydrocarbon groups having 1 to 20 carbon atoms, groups having a divalent heteroatom-containing group between carbon atoms of the hydrocarbon group or at the carbon chain terminal, groups in which some or all of the hydrogen atoms of the hydrocarbon group have been substituted with monovalent heteroatom-containing groups, and combinations thereof.

[0035] Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms for Y include a chain hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.

[0036] Examples of the monovalent chain hydrocarbon group having 1 to 20 carbon atoms represented by Y include monovalent linear or branched saturated hydrocarbon groups having 1 to 20 carbon atoms, and monovalent linear or branched unsaturated hydrocarbon groups having 2 to 20 carbon atoms. Examples of the monovalent linear or branched saturated hydrocarbon groups having 1 to 20 carbon atoms include alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, 2-methylpropyl, 1-methylpropyl, t-butyl, n-pentyl, isopentyl, and neopentyl. Examples of the monovalent linear or branched unsaturated hydrocarbon groups having 2 to 20 carbon atoms include alkenyl groups such as ethenyl, propenyl, and butenyl; and alkynyl groups such as ethynyl, propynyl, and butynyl.

[0037] The monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms represented by Y includes monocyclic or polycyclic saturated hydrocarbon groups, and monocyclic or polycyclic unsaturated hydrocarbon groups. Examples of monocyclic saturated hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic saturated hydrocarbon groups include bridged alicyclic hydrocarbon groups such as norbornyl, adamantyl, tricyclodecyl, and tetracyclododecyl. Examples of monocyclic unsaturated hydrocarbon groups include monocyclic cycloalkenyl groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl. Examples of polycyclic unsaturated hydrocarbon groups include polycyclic cycloalkenyl groups such as norbornenyl, tricyclodecenyl, and tetracyclododecenyl. The bridged alicyclic hydrocarbon group refers to a polycyclic alicyclic hydrocarbon group in which two carbon atoms that are not adjacent to each other among the carbon atoms that constitute the alicyclic ring are linked by a linking group containing one or more carbon atoms.

[0038] Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms represented by Y include aryl groups such as phenyl, tolyl, xylyl, naphthyl, and anthryl; and aralkyl groups such as benzyl, phenethyl, and naphthylmethyl.

[0039] Examples of the monovalent heteroatom-containing group include a hydroxy group, a carboxy group, a sulfanyl group, a cyano group, a nitro group, and a halogen atom.

[0040] Examples of the divalent heteroatom-containing group include -CO-, -C(=O)O-, -CS-, -NR'-, -O-, -S-, -SO-, -SO2-, and combinations thereof, where R' is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

[0041] The above Y is preferably a group represented by the following formula (4). [ka] (In the above formula (4), R 1 are each independently a hydrogen atom or a methyl group. 2 are each independently an alkanediyl group having 2 to 10 carbon atoms. 3 is a divalent organic group. 1 is a carboxy group, a carboxylic acid anhydride group, a phenolic hydroxyl group, or a combination thereof.

[0042] Above R 2 The alkanediyl group having 2 to 10 carbon atoms represented by the formula (1) has the same meaning as that of the formula (1).

[0043] Above R 3 As the divalent organic group represented by the following formula, a group obtained by removing one hydrogen atom from the monovalent organic group explained above for Y can be suitably used.

[0044] The above formula (4) is preferably a group selected from the group consisting of groups represented by the following formula (4a), (4b), and (4c). [ka] (In the above formulas (4a), (4b), and (4c), R 4 is a single bond or a divalent organic group. X is a halogen atom, a hydroxy group, a carboxy group, a cyano group, a nitro group, an alkyl group, or an alkoxy group. n is an integer of 0 to 4. When n is 2 or more, multiple Xs may be the same or different. R 1 , R 2 , R 3 is the same as in formula (4). * indicates a binding site.

[0045] Above R 4 As the divalent organic group represented by the following formula, a group obtained by removing one hydrogen atom from the monovalent organic group explained above for Y can be suitably used.

[0046] Examples of the alkyl group represented by X include the chain hydrocarbon group having 1 to 20 carbon atoms represented by Y above.

[0047] Examples of the alkyl group moiety of the alkoxy group represented by X include the alkyl groups described above.

[0048] n is an integer of 0 to 4, with 0 or 1 being preferred.

[0049] Specific examples of the structural unit (II) include, but are not limited to, structures represented by the following formula: 1 has the same meaning as the above formula (4), and m is an integer of 2 to 4.

[0050] [ka]

[0051] The lower limit of the content of the structural unit (I) relative to the total content of the structural unit (I) and the structural unit (II) in the silsesquioxane (A) is preferably 10 mol%, more preferably 30 mol%, even more preferably 50 mol%, and particularly preferably 60 mol%. The upper limit of the content is preferably 100 mol%, more preferably 95 mol%, and even more preferably 90 mol%. By setting the content of the structural unit (I) within the above range, lithography performance can be improved, which is preferable.

[0052] The silsesquioxane (A) may have structural units other than the structural units (I) and (II). Examples of such structural units include a structural unit having a silanol group (—SiOH) and a structural unit having a —(R a SiO 1.5 )-(R a is a monovalent hydrocarbon group) (excluding those corresponding to structural unit (I) and structural unit (II)).

[0053] The lower limit of the total content of the structural units (I) and (II) relative to all structural units contained in the silsesquioxane (A) is preferably 60 mol%, more preferably 70 mol%, and even more preferably 80 mol%. The upper limit of the total content is not particularly limited and may be 100 mol%.

[0054] The lower limit of the weight average molecular weight (Mw) of the silsesquioxane (A) is preferably 1,000, more preferably 2,000, and even more preferably 3,000. The upper limit of the weight average molecular weight is preferably 20,000, more preferably 10,000, and even more preferably 6,000.

[0055] The lower limit of the content of silsesquioxane (A) in the composition is preferably 10% by mass, more preferably 15% by mass, and even more preferably 20% by mass, based on the total solids content (100% by mass) of the composition. Meanwhile, the upper limit of this content is preferably 90% by mass, more preferably 80% by mass, even more preferably 70% by mass, and particularly preferably 60% by mass. The total solids content refers to all components other than solvents such as organic solvent (G). Setting the content of silsesquioxane (A) within the above range is preferable because it can further improve storage stability and suppress the generation of residues and outgassing.

[0056] The method for producing the silsesquioxane (A) is not particularly limited, but it can be synthesized, for example, by the following synthesis method.

[0057] (synthesis method) The synthesis scheme (M-1) is shown below.

[0058] [ka]

[0059] In the above scheme (M-1), R 11 is an alkyl group having 1 to 6 carbon atoms. k, m, and n are natural numbers that satisfy the equation k=m+n. X and Y have the same meanings as X and Y in formulas (1) and (3).

[0060] The trialkoxysilane represented by the formula (1A) is used as a starting material and is subjected to hydrolysis and condensation in the presence of a base to obtain the silsesquioxane represented by the formula (1). Subsequently, the silsesquioxane is subjected to an addition reaction with an SH compound to obtain the silsesquioxane (A).

[0061] Examples of trialkoxysilanes represented by the formula (1A) include acryloxypropyltrimethoxysilane, methacryloxypropyltrimethoxysilane, acryloxypropyltriethoxysilane, methacryloxypropyltriethoxysilane, acryloxyoctyltrimethoxysilane, methacryloxyoctyltrimethoxysilane, acryloxyoctyltriethoxysilane, and methacryloxyoctyltriethoxysilane, etc. Among these, acryloxypropyltrimethoxysilane and methacryloxypropyltrimethoxysilane are more preferred.

[0062] Other trialkoxysilanes may also be used together with the trialkoxysilane represented by formula (1A). Examples of other trialkoxysilanes include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, pentyltrimethoxysilane, pentyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, 4-vinylphenyltrimethoxysilane, and 4-vinylphenyltriethoxysilane.

[0063] Examples of the base used in the hydrolysis and condensation reaction include trimethylamine, triethylamine, tripropylamine, imidazole, diazabicycloundecene, pyridine, morpholine, piperazine, piperidine, sodium hydroxide, potassium hydroxide, etc. Among these, triethylamine is preferred.

[0064] The SH compound in the above scheme (M-1) can be a monovalent thiol compound having a carboxy group, a carboxylic anhydride group, a phenolic hydroxyl group, or a combination thereof. Examples of the addition reaction of the SH compound include the Michael addition reaction and the ene-thiol reaction, with the Michael addition reaction being preferred. Specific examples of the SH compound include compounds represented by the following formulae (SH-1) to (SH-20). Of these, the compounds represented by the following formulae (SH-1) to (SH-12) are preferred, the compounds represented by the following formulae (SH-1) to (SH-9) are more preferred, and the compounds represented by the following formulae (SH-1) and (SH-5) are even more preferred.

[0065] [ka]

[0066] Examples of the base used in the Michael addition reaction include trimethylamine, triethylamine, tripropylamine, imidazole, diazabicycloundecene, pyridine, morpholine, piperazine, piperidine, sodium hydroxide, potassium hydroxide, etc. Among these, triethylamine is preferred.

[0067] An example of the synthesis method is shown in the following scheme (M-1-1).

[0068] [ka]

[0069] <Alkali-soluble resin (B)> The alkali-soluble resin (B) is a component that can exhibit good developability with an alkaline developer. The alkali-soluble resin (B) is usually a resin having an acidic group such as a carboxy group or a phenolic hydroxyl group (excluding those corresponding to the silsesquioxane (A)), and a resin having a carboxy group is preferred.

[0070] Examples of the alkali-soluble resin (B) include acrylic resins, polysiloxane resins, and novolak resins, with acrylic resins being preferred from the viewpoint of storage stability.

[0071] The alkali-soluble resin (B) preferably has a group containing an unsaturated double bond, such as a (meth)acryloyl group or a vinyl group, from the viewpoint of further improving developability and the physical properties of the cured product. Examples of such alkali-soluble resins (B) include acid-modified epoxy (meth)acrylate resins, such as acid-modified cresol novolac epoxy (meth)acrylate resins, phenol novolac epoxy (meth)acrylate resins, bisphenol A epoxy (meth)acrylate resins, bisphenol F epoxy (meth)acrylate resins, biphenyl epoxy (meth)acrylate resins, and trisphenolmethane epoxy (meth)acrylate resins. Examples of alkali-soluble resins (B) include acid-modified cardo resins having a (meth)acryloyl group and a carboxy group.

[0072] (acrylic resin) The acrylic resin may be a copolymer of a monomer having an alkali-soluble functional group and another copolymerizable monomer.

[0073] Examples of the monomer having an alkali-soluble functional group include: Carboxyl group-containing monomers such as (meth)acrylic acid, maleic acid, fumaric acid, crotonic acid, itaconic acid, citraconic acid, mesaconic acid, cinnamic acid, mono(2-(meth)acryloyloxyethyl) succinate, and ω-carboxy-polycaprolactone mono(meth)acrylate; hydroxyl group-containing monomers such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 3-hydroxypropyl (meth)acrylate; Examples include phenolic hydroxyl group-containing monomers such as o-hydroxystyrene, m-hydroxystyrene, and p-hydroxystyrene.

[0074] Examples of the other copolymerizable monomers include: (meth)acrylic acid esters such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, glycidyl (meth)acrylate, and dicyclopentadienyl (meth)acrylate; Aromatic vinyl monomers such as styrene, α-methylstyrene, and vinyltoluene; conjugated dienes such as butadiene and isoprene; unsaturated imides such as phenylmaleimide and cyclohexylmaleimide; vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, and α-chloroacrylonitrile; Examples include macromonomers having a polymerizable unsaturated group such as a (meth)acryloyl group at one end of a polymer chain, such as polystyrene, polymethyl(meth)acrylate, polyethyl(meth)acrylate, polybenzyl(meth)acrylate, etc. These may be used alone or in combination of two or more.

[0075] The lower limit of the content of the monomer having an alkali-soluble functional group is preferably 5% by mass, more preferably 8% by mass, based on the total amount of monomers (100% by mass) constituting the acrylic resin, and the upper limit is not particularly limited, but is, for example, preferably 40% by mass, more preferably 30% by mass.

[0076] The method for producing the acrylic resin is not particularly limited, and the resin can be produced by a known method such as suspension polymerization, emulsion polymerization, bulk polymerization, solution polymerization, etc. The production conditions can also be conventionally known conditions.

[0077] (Polysiloxane resin) The polysiloxane resin may be a hydrolysis condensate of a hydrolyzable silane compound. Here, the term "hydrolyzable silane compound" refers to a compound containing a group capable of hydrolyzing to form a silanol group or a group capable of forming a siloxane condensate, and the term "hydrolysis condensate" refers to a condensate formed by condensation of silanol groups from hydrolyzed silane compounds. Examples of such polysiloxane resins include those described in JP 2017-048355 A. Silsesquioxanes may also be used, such as those having a molar ratio of silanol groups to the total content of structural units constituting the silsesquioxane of 0.3 or more, or silsesquioxanes that do not have a group represented by formula (2) (i.e., neither of these silsesquioxanes fall under the category of silsesquioxane (A)).

[0078] (Novolac resin) The novolak resin can be obtained by polycondensing a phenol with an aldehyde such as formaldehyde using a known method.

[0079] Examples of the phenols include phenol, p-cresol, m-cresol, o-cresol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2,3,4-trimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol, 2,4,5-trimethylphenol, methylenebisphenol, methylenebis-p-cresol, resorcinol, catechol, 2-methylresorcinol, 4-methylresorcinol, o-chlorophenol, m-chlorophenol, p-chlorophenol, 2,3-dichlorophenol, m-methoxyphenol, p-methoxyphenol, p-butoxyphenol, o-ethylphenol, m-ethylphenol, p-ethylphenol, 2,3-diethylphenol, 2,5-diethylphenol, p-isopropylphenol, α-naphthol, and β-naphthol. These may be used alone or in combination of two or more.

[0080] Furthermore, examples of the aldehydes include, in addition to formaldehyde, paraformaldehyde, acetaldehyde, benzaldehyde, hydroxybenzaldehyde, chloroacetaldehyde, etc. These may be used alone or in combination of two or more.

[0081] The novolac resin preferably has a group containing an unsaturated double bond such as a (meth)acryloyl group or a vinyl group, and more preferably has a side chain represented by the following formula (5). In this case, it is preferable that the main chain further contains an aromatic ring. Among these, a resin having a side chain represented by the following formula (5) and a phenolic novolac main chain is more preferred.

[0082] Examples of the resin having a side chain represented by the following formula (5) and a phenolic novolac main chain include an acid-modified cresol novolac epoxy (meth)acrylate resin and an acid-modified phenolic novolac epoxy (meth)acrylate resin.

[0083] [ka]

[0084] In the above formula (5), R 5 is a hydrogen atom or a methyl group. 6 and R 7 are each independently a divalent organic group. * represents the bonding site to the main chain.

[0085] Above R 5 is preferably a hydrogen atom.

[0086] Above R 6 and R 7 As the divalent organic group represented by the formula (3), a group in which one hydrogen atom has been removed from the monovalent organic group represented by Y in the formula (3) can be suitably used.

[0087] Above R6 and R 7 The number of carbon atoms in the divalent organic group represented by the formula (I) is not particularly limited, and the lower limit may be 1. On the other hand, the upper limit of the number of carbon atoms may be, for example, 20 or 10.

[0088] Above R 6 As the R, a divalent hydrocarbon group is preferred, and a divalent chain hydrocarbon group and a divalent alicyclic hydrocarbon group are more preferred. 7 As the alkyl group, a group in which an oxygen atom (-O-) is bonded to the main chain terminal of a divalent hydrocarbon group, such as -CH2-O-*, is preferred.

[0089] An example of the acid-modified cresol novolac epoxy (meth)acrylate resin is a polymer represented by the following formula (6): The acid-modified cresol novolac epoxy (meth)acrylate resin can be obtained, for example, by reacting a cresol novolac epoxy resin with (meth)acrylic acid to obtain an epoxy (meth)acrylate resin, and then reacting the resulting epoxy (meth)acrylate resin with an acid anhydride such as phthalic anhydride or 1,2,3,6-tetrahydrophthalic anhydride.

[0090] [ka]

[0091] In the above formula (6), p and q each independently represent an integer of 1 to 30.

[0092] The alkali-soluble resin (B) may also be a cardo resin having a side chain represented by the above formula (5) and modified with a specific acid. Commercially available examples of such resins include the acid-modified cardo resin "WR-301" (ADEKA Corporation).

[0093] The lower limit of the acid value of the alkali-soluble resin (B) is preferably 10 mg KOH / g, more preferably 20 mg KOH / g, and even more preferably 40 mg KOH / g. The upper limit of the acid value is preferably 300 mg KOH / g, more preferably 270 mg KOH / g, and even more preferably 250 mg KOH / g. The acid value represents the number of mg of KOH required to neutralize 1 g of the solid content of the alkali-soluble resin (B).

[0094] The weight average molecular weight (Mw) of the alkali-soluble resin (B) is preferably 1,000 or more and 20,000 or less.

[0095] The alkali-soluble resin (B) may be used singly or in combination of two or more.

[0096] The lower limit of the content of alkali-soluble resin (B) (total amount when multiple types are used) is preferably 5% by mass, more preferably 10% by mass, even more preferably 20% by mass, and particularly preferably 30% by mass, based on the total solid content (100% by mass) of the composition. The upper limit is preferably 90% by mass, more preferably 80% by mass, even more preferably 70% by mass, and particularly preferably 60% by mass, based on the total solid content (100% by mass) of the composition. By ensuring that the content of alkali-soluble resin (B) is within the above range, more satisfactory lithography performance can be achieved.

[0097] <Radiation-sensitive radical polymerization initiator (D)> The radiation-sensitive radical polymerization initiator (D) is a compound that generates radicals in response to radiation and can initiate polymerization. Specific examples of the radiation-sensitive radical polymerization initiator (D) include O-acyloxime compounds, α-aminoketone compounds, α-hydroxyketone compounds, and acylphosphine oxide compounds. Among these, oxime-based photopolymerization initiators such as O-acyloxime compounds are preferred.

[0098] Use of the oxime ester photoinitiator can improve sensitivity, and is preferable from the viewpoint of suppressing in-plane line width variations and improving film remaining rate when forming a fine line pattern.

[0099] As the oxime ester photoinitiator, from the viewpoint of reducing contamination of the composition and the equipment due to decomposition products, those having an aromatic ring are preferred, those having a fused ring containing an aromatic ring are more preferred, and those having a fused ring containing a benzene ring and a heterocycle are even more preferred.

[0100] Examples of oxime ester photoinitiators include 1,2-octadione-1-[4-(phenylthio)phenyl-2-(O-benzoyloxime)], ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), and oxime ester photoinitiators described in JP-A-2000-80068, JP-A-2001-233842, JP-T-2010-527339, JP-T-2010-527338, JP-A-2013-041153, and JP-A-2021-076846. Commercially available products include Irgacure OXE-01, Irgacure OXE-02, Irgacure OXE-03 (all manufactured by BASF), ADEKA Arcles NCI-930 having a diphenyl sulfide skeleton (manufactured by ADEKA), TR-PBG-345, TR-PBG-304 having a carbazole skeleton, TR-PBG-365 having a fluorene skeleton, and TR-PBG-3057 having a diphenyl sulfide skeleton (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.).

[0101] The above radiation-sensitive radical polymerization initiators (D) can be used alone or in combination of two or more.

[0102] The lower limit of the content of the radiation-sensitive radical polymerization initiator (D) (total amount when multiple types are used) is preferably 1% by mass, more preferably 3% by mass, based on the total solids content (100% by mass) of the composition. Meanwhile, the upper limit of the content is preferably 40% by mass, more preferably 30% by mass. By keeping the content of component (D) within the above range, the composition can form a cured product with good resolution and development adhesion, even at low exposure doses, which is preferable.

[0103] <Color material (C)> The present composition contains a coloring material (C). By including the coloring material (C), it is possible to impart a desired color to the photosensitive composition depending on the intended use.

[0104] The coloring material (C) is not particularly limited, and may be any of an organic pigment, an inorganic pigment, and a dye.

[0105] Examples of the organic pigments include compounds classified as pigments in the Colour Index (CI; published by The Society of Dyers and Colourists), specifically compounds assigned the following Colour Index (CI) numbers:

[0106] Yellow pigments such as CI Pigment Yellow 12, CI Pigment Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 17, CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 31, CI Pigment Yellow 55, CI Pigment Yellow 83, CI Pigment Yellow 93, CI Pigment Yellow 109, CI Pigment Yellow 110, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Yellow 153, CI Pigment Yellow 154, CI Pigment Yellow 155, CI Pigment Yellow 166, CI Pigment Yellow 168, CI Pigment Yellow 180, CI Pigment Yellow 211, etc. Orange pigments such as CI Pigment Orange 5, CI Pigment Orange 13, CI Pigment Orange 14, CI Pigment Orange 24, CI Pigment Orange 34, CI Pigment Orange 36, CI Pigment Orange 38, CI Pigment Orange 40, CI Pigment Orange 43, CI Pigment Orange 46, CI Pigment Orange 49, CI Pigment Orange 61, CI Pigment Orange 64, CI Pigment Orange 68, CI Pigment Orange 70, CI Pigment Orange 71, CI Pigment Orange 72, CI Pigment Orange 73, CI Pigment Orange 74, etc.; CI Pigment Red 1, CI Pigment Red 2, CI Pigment Red 5, CI Pigment Red 17, CI Pigment Red 31, CI Pigment Red 32, CI Pigment Red 41, CI Pigment Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 170, CI Pigment Red 171, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 178, CI Pigment Red red pigments such as CI Pigment Red 179, CI Pigment Red 180, CI Pigment Red 185, CI Pigment Red 187, CI Pigment Red 202, CI Pigment Red 206, CI Pigment Red 207, CI Pigment Red 209, CI Pigment Red 214, CI Pigment Red 220, CI Pigment Red 221, CI Pigment Red 224, CI Pigment Red 242, CI Pigment Red 243, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 262, CI Pigment Red 264, and CI Pigment Red 272; Violet pigments such as CI Pigment Violet 1, CI Pigment Violet 19, CI Pigment Violet 23, CI Pigment Violet 29, CI Pigment Violet 32, CI Pigment Violet 36, CI Pigment Violet 38; Blue pigments such as CI Pigment Blue 15, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 60, CI Pigment Blue 80; Green pigments such as CI Pigment Green 7, CI Pigment Green 36, CI Pigment Green 58, CI Pigment Green 59; Brown pigments such as CI Pigment Brown 23, CI Pigment Brown 25; Black pigments such as CI Pigment Black 1, CI Pigment Black 7, CI Pigment Black 31, CI Pigment Black 32, lactam-based black pigments, and perylene-based black pigments.

[0107] In the present invention, the organic pigment may be used after being purified by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof.

[0108] Examples of the inorganic pigments include titanium oxide, barium sulfate, calcium carbonate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, iron blue, chromium oxide green, cobalt green, umber, titanium black, synthetic iron black, and carbon black.

[0109] If desired, the particle surfaces of these colorants may be modified with a polymer before use. Examples of polymers that modify the pigment particle surfaces include the polymers described in JP-A-8-259876 and various commercially available polymers or oligomers for dispersing pigments. Methods for coating carbon black surfaces with polymers are disclosed in, for example, JP-A-9-71733, JP-A-9-95625, and JP-A-9-124969.

[0110] The black coloring material may be a single black coloring material or a black coloring material made by mixing coloring materials such as red, green, blue, etc. These black coloring materials may be appropriately selected from inorganic or organic pigments and dyes, and may be used alone or in combination.

[0111] Examples of the single black colorant include organic pigments and inorganic pigments such as carbon black, acetylene black, lamp black, bone black, graphite, iron black, aniline black, perylene black, lactam black, cyanine black, and titanium black.

[0112] As the dye, one that develops a desired color is used, and examples of the specific structural moiety (chromophore) that is the source of the color development include triarylmethane-based cationic chromophores, methine-based cationic chromophores, azo-based cationic chromophores, diarylmethane-based cationic chromophores, quinoneimine-based cationic chromophores, anthraquinone-based cationic chromophores, cyanine-based cationic chromophores, squarylium-based cationic chromophores, and xanthene-based cationic chromophores.

[0113] When the present composition is used to form a light-shielding barrier rib material, a black organic pigment, titanium black or carbon black is preferably used as the coloring material (C) from the viewpoint of preventing light leakage from the adjacent light-emitting layer.

[0114] When a pigment is used as the colorant (C), it is preferable to carry out a dispersion treatment using a pigment dispersant, since this allows the present composition to be obtained in a state in which the pigment is uniformly dispersed. In this case, the pigment and the pigment dispersant may be used when preparing the present composition, but it is preferable to prepare a pigment dispersion in advance by mixing the pigment, the pigment dispersant, and a dispersion medium before preparing the present composition, and then prepare the present composition using the prepared pigment dispersion.

[0115] Examples of the pigment dispersant include cationic pigment dispersants, anionic pigment dispersants, nonionic pigment dispersants, and amphoteric pigment dispersants. Specific examples include polyester pigment dispersants, polyamine pigment dispersants, and acrylic pigment dispersants. One or more of the pigment dispersants may be used.

[0116] When the pigment dispersant is used, the amount used is preferably 100 parts by mass or less, and more preferably 5 to 50 parts by mass, per 100 parts by mass of the pigment, from the viewpoint that a pigment dispersion in which the pigment is uniformly dispersed can be easily obtained.

[0117] The coloring material (C) can be used alone or in combination of two or more kinds.

[0118] The lower limit of the content of the colorant (C) (total amount when multiple types are used) is preferably 1% by mass, more preferably 5% by mass, and even more preferably 10% by mass, based on the total solid content (100% by mass) of the composition. On the other hand, the upper limit of the content is preferably 50% by mass, more preferably 40% by mass, even more preferably 30% by mass, and particularly preferably 20% by mass. By setting the content of the colorant (C) within the above range, it is possible to achieve both developability and a suitable coloring degree, which is preferable.

[0119] <Polymerizable compound (E)> The composition may contain a polymerizable compound (E). The polymerizable compound (E) is a compound having preferably two or more polymerizable groups and functions as a crosslinking agent. The polymerizable group is preferably a radically polymerizable group, such as an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, or an N-alkoxymethylamino group. Of these, the polymerizable compound (E) is preferably a compound having two or more (meth)acryloyl groups.

[0120] Specific examples of compounds having two or more (meth)acryloyl groups include polyfunctional (meth)acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth)acrylic acid, caprolactone-modified polyfunctional (meth)acrylates, alkylene oxide-modified polyfunctional (meth)acrylates, polyfunctional urethane (meth)acrylates obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate, and polyfunctional (meth)acrylates having a carboxyl group obtained by reacting a (meth)acrylate having a hydroxyl group with an acid anhydride.

[0121] Among these, the polymerizable compound (E) is preferably a polyfunctional (meth)acrylate obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth)acrylic acid, a caprolactone-modified polyfunctional (meth)acrylate, a polyfunctional urethane (meth)acrylate, or a polyfunctional (meth)acrylate having a carboxyl group, and more preferably a polyfunctional (meth)acrylate obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth)acrylic acid, a polyfunctional urethane (meth)acrylate, or a polyfunctional (meth)acrylate having a carboxyl group. Among the polyfunctional (meth)acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth)acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate are particularly preferred.

[0122] Commercially available products include, for example, Aronix M-400, Aronix M-460, Aronix M-402, Aronix M-510, and Aronix M-520 (manufactured by Toagosei Co., Ltd.), KAYARAD T-1420, KAYARAD DPHA, KAYARAD DPCA20, KAYARAD DPCA30, KAYARAD DPCA60, and KAYARAD Examples of suitable esters include DPCA120 (manufactured by Nippon Kayaku Co., Ltd.), Viscoat #230, Viscoat #300, Viscoat #802, Viscoat #2500, Viscoat #1000, and Viscoat #1080 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), NK Ester A-BPE-10, NK Ester A-GLY-9E, NK Ester A-9550, and NK Ester A-DPH (manufactured by Shin-Nakamura Chemical Co., Ltd.), and UA-306H and UA-306I (manufactured by Kyoeisha Chemical Co., Ltd.).

[0123] The polymerizable compound (E) can be used alone or in combination of two or more.

[0124] The lower limit of the content of the polymerizable compound (E) (total amount when multiple types are used) is preferably 3% by mass, more preferably 5% by mass, based on the total solid content (100% by mass) of the composition. The upper limit of the content is preferably 70% by mass, more preferably 60% by mass, based on the total solid content of the composition. A content of the polymerizable compound (E) within the above range is preferable because it ensures sufficient curability as a coating film and sufficient alkali developability as a photosensitive coloring composition, while also adequately suppressing the generation of outgassing, etc.

[0125] <Organic solvent (G)> The composition contains an organic solvent (G). The organic solvent (G) is not particularly limited, and examples thereof include alcohol-based solvents, ether-based solvents, ester-based solvents, ketone-based solvents, and amide-based solvents. The organic solvent (G) may be used alone or in combination of two or more.

[0126] Examples of alcohol solvents include alkyl alcohols such as methanol, ethanol, isopropyl alcohol, 1-butanol, 2-butanol, isobutyl alcohol, t-butyl alcohol, 1-hexanol, 1-octanol, 1-nonanol, 1-dodecanol, 1-methoxy-2-propanol, and diacetone alcohol; and aromatic alcohols such as benzyl alcohol.

[0127] Examples of ether solvents include ethylene glycol monoalkyl ethers such as diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether; diethylene glycol monoalkyl ethers such as diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether and diethylene glycol ethyl methyl ether; and dipropylene glycol monoalkyl ethers such as dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, and dipropylene glycol monobutyl ether.

[0128] Examples of ester-based solvents include carboxylic acid esters such as ethyl acetate, i-propyl acetate, n-butyl acetate, amyl acetate, ethyl lactate, methyl 3-methoxypropionate, and ethyl 3-ethoxypropionate; polyhydric alcohol carboxylate-based solvents such as propylene glycol diacetate; and polyhydric alcohol partial ether carboxylate-based solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate.

[0129] Examples of ketone solvents include acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, methyl amyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, and cycloheptanone.

[0130] Among these, ether solvents and ester solvents are preferred, ester solvents are more preferred, and polyhydric alcohol partial ether carboxylate solvents are even more preferred. Among the ether solvents and ester solvents, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, and methyl 3-methoxypropionate are preferred.

[0131] The content of organic solvent (G) in the composition is not particularly limited, but it is preferable that the solid content (components other than the solvent, such as organic solvent (G)) of the composition be adjusted to be within the following range: The lower limit of the solid content of the composition is preferably 5% by mass, more preferably 10% by mass, and even more preferably 15% by mass. Meanwhile, the upper limit of the solid content is preferably 60% by mass, more preferably 50% by mass, and even more preferably 40% by mass.

[0132] <Other ingredients> The present composition may further contain other components in addition to the components described above. Examples of other components include curing agents, curing accelerators, antioxidants, and surfactants such as fluorine-based surfactants and silicone-based surfactants. However, the content of other components in the curable composition is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 1% by mass or less.

[0133] <Method for preparing photosensitive coloring composition> The photosensitive coloring composition of the present invention can be prepared by mixing the components in a predetermined ratio and dissolving them in an organic solvent (G). The prepared composition is preferably filtered, for example, through a filter having a pore size of about 0.2 μm.

[0134] ≪Cured product≫ The cured product of the present invention (hereinafter also referred to as "the present cured product") can be formed by curing the photosensitive coloring composition prepared as described above. The photosensitive coloring composition has high storage stability and high radiation sensitivity. The cured product obtained from the photosensitive coloring composition is one in which the generation of residues and outgassing is suppressed. Therefore, the cured product can be preferably used as, for example, a color filter (color pattern or black matrix) or a light-shielding partition material (bank). In addition to the above, it can also be suitably used as an interlayer insulating film, a planarizing film, etc.

[0135] When a cured product formed by curing the curable composition of the present invention is used as a light-shielding partition wall material, the optical density (OD value) of the cured product is preferably 0.5 to 4.0, more preferably 0.7 to 3.5. When the optical density is in the above range, the cured product can exhibit sufficient light-shielding properties as a light-shielding partition wall material, which is preferable.

[0136] The cured product of the present invention may be a patterned film.

[0137] <Method for producing cured product> The method for producing a patterned cured product in this embodiment includes the steps of: A step of applying the photosensitive coloring composition onto a substrate to form a coating film (coating film forming step); a step of regioselectively exposing the coating film to light (exposure step); a step of developing the exposed coating film (developing step); a step of heating the developed pattern (heating step); Includes.

[0138] According to the method for producing a cured product, since the photosensitive coloring composition is used, it is possible to form a patterned cured product in which the generation of residues and outgassing is suppressed. Each step will be described below.

[0139] [Process 1: Paint film formation process] In this process, the photosensitive coloring composition is applied to a surface on which a film is to be formed (hereinafter also referred to as "film-forming surface"), and the solvent is preferably removed by a heat treatment (pre-bake) to form a coating film on the film-forming surface. The material of the film-forming surface is not particularly limited. For example, the photosensitive coloring composition is applied to a substrate provided with switching elements such as TFTs to form a coating film. Examples of the substrate that can be used include a glass substrate, a silicon substrate, and a resin substrate. The surface of the substrate on which the coating film is to be formed may have a metal thin film formed depending on the application, or may have been subjected to various surface treatments such as HMDS (hexamethyldisilazane) treatment.

[0140] Examples of methods for applying the photosensitive coloring composition include spraying, roll coating, spin coating, slit die coating, bar coating, and inkjet coating. Among these, spin coating, slit die coating, and bar coating are preferred. Pre-baking conditions vary depending on the type and content of each component in the photosensitive coloring composition, but are, for example, 60 to 130°C and 0.5 to 10 minutes. The thickness of the coating film formed (i.e., the film thickness after pre-baking) is preferably 0.1 to 12 μm. The photosensitive coloring composition applied to the surface to be coated may be subjected to reduced pressure drying (VCD) before pre-baking.

[0141] [Step 2: Exposure step] In this step, radiation is irradiated regioselectively onto at least a portion of the coating film formed in step 1 above. The term "regioselectively" means that radiation is partially irradiated onto the coating film through a mask having a predetermined pattern. By exposing the coating film regioselectively, a cured product having a pattern can be formed. Examples of radiation include charged particle beams such as ultraviolet light, far ultraviolet light, visible light, X-rays, and electron beams. Among these, ultraviolet light is preferred, and examples thereof include g-rays (wavelength 436 nm), h-rays (wavelength 405 nm), and i-rays (wavelength 365 nm). The radiation exposure dose is 0.1 to 20,000 J / m 2 is preferred.

[0142] [Process 3: Development process] In this step, the coating film irradiated in step 2 is developed. Specifically, the coating film irradiated in step 2 is developed using a developer to remove the irradiated portions (positive development), or to remove the unirradiated portions (negative development). Examples of the developer include an aqueous solution of an alkali (basic compound). Examples of alkali include sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, and the alkalis exemplified in paragraph

[0127] of JP 2016-145913 A. The alkali concentration in the aqueous alkali solution is preferably 0.01 to 5% by mass to obtain adequate developability. Examples of the development method include a puddle method, a dipping method, a swing immersion method, and a shower method. The development time varies depending on the composition of the composition, but is, for example, 30 to 120 seconds. After the development step, the patterned coating film is preferably rinsed with running water.

[0143] [Process 4: Heating process] In this step, the coating film developed in step 3 above is subjected to a heating treatment (post-baking). Post-baking can be performed using a heating device such as an oven or a hot plate. Regarding post-baking conditions, the heating temperature is, for example, 120 to 250°C. The heating time is, for example, 5 to 40 minutes when the heating treatment is performed on a hot plate, and 10 to 80 minutes when the heating treatment is performed in an oven. In this manner, a cured product having a desired pattern can be formed on a substrate. The shape of the pattern of the cured product is not particularly limited, and can be, for example, a line and space pattern, a dot pattern, a hole pattern, A grid pattern is an example.

[0144] A cured product formed using the photosensitive coloring composition can be preferably used, for example, as a color filter (color pattern or black matrix), a light-shielding partition wall material, etc. In addition to the above, it can also be suitably used as an interlayer insulating film, a planarizing film, etc.

[0145] <Color filter> The color filter of the present invention may include the cured product as a color pattern having each color (RGB), or may include the cured product as a black matrix.

[0146] <Image display panel> The image display panel of the present invention is not particularly limited in other configuration as long as it includes the above-mentioned color filter. Also suitable is an organic EL panel having a polarizing plate-less (POL-LESS) structure, in which, as shown in Fig. 1, a TFT drive circuit layer 2, a light-shielding partition material (bank) 3, a light-emitting layer of three primary colors having a light-emitting layer 4, a sealing layer 8, a touch sensor 5, a color filter 6 including a black matrix 6a and a color pattern 6b having each color (RGB), and a cover glass 7 are laminated on a substrate 1. The present cured product can be used as the color filter or light-shielding partition material of such an organic EL panel having a POL-LESS structure.

[0147] Image display device The image display device of the present invention includes the present cured product and the image display panel. The present cured product can be used as a light-shielding partition wall material. Examples of the display device include liquid crystal display devices, organic EL display devices, micro LED (Light Emitting Diode) display devices, and quantum dot luminescent display devices. Another suitable example is an organic EL display device having an organic EL panel with a pole-less structure (POL-LESS) that does not have a polarizing plate, as shown in FIG. 1. [Example]

[0148] The present invention will be specifically described below based on examples, but the present invention is not limited to these examples.

[0149] [Weight average molecular weight (Mw)] The Mw was measured by gel permeation chromatography (GPC) under the following conditions. Device: Showa Denko "GPC-101" Column: Showa Denko K.K. "GPC-KF-801", "GPC-KF-802", "GPC-KF-803" and "GPC-KF-804" connected together Mobile phase: tetrahydrofuran Column temperature: 40℃ Flow rate: 1.0mL / min Sample concentration: 1.0% by mass Sample injection volume: 100 μL Detector: differential refractometer Standard material: monodisperse polystyrene

[0150] <Compounds used in synthesis> The compounds used in the synthesis are shown below. Silsesquioxane (AC-SQ): "AC-SQ TA-100" manufactured by Toagosei Co., Ltd.: a silsesquioxane having the following structural unit: [ka]

[0151] SH compounds: the following compounds (SH-1) to (SH-9) [ka]

[0152] Silane compounds: the following compounds (TAS-1) to (TAS-8) [ka]

[0153] [Synthesis Example 1] Synthesis of silsesquioxane (A-1) A 300 mL three-neck flask equipped with a thermometer was charged with 50.0 g (210 mmol) of compound (TAS-1), 50 mL of ethyl acetate, and 0.2 g (0.1 mmol) of 4-methoxyphenol, and the mixture was heated to 30 °C with stirring. Then, 4.8 g (47.4 mmol) of triethylamine and 12.7 g of ultrapure water were slowly added, and the mixture was heated to 60 °C and stirred for 3 hours. The mixture was then cooled to 30 °C with stirring, and 2.3 g (21.7 mmol) of compound (SH-1) was added. The reaction was continued at 50 °C for 2 hours. At this point, GPC analysis revealed a weight-average molecular weight (Mw) of 4400, and the remaining amount of compound (SH-1) was less than 0.1%, confirming that the Michael addition reaction had proceeded quantitatively. After the reaction was complete, the mixture was transferred to a separatory funnel, 100 mL of ethyl acetate was added, and the mixture was washed once with 100 mL of 1 M aqueous hydrochloric acid and three times with 50 mL of water. Next, 80 g of propylene glycol monomethyl ether acetate (PGMEA) was added, and the mixture was concentrated to a liquid volume of 100 g. Then, 80 g of PGMEA was added and the mixture was concentrated again. The solid content was then adjusted to 50% with PGMEA, yielding a solution of silsesquioxane (A-1). The weight-average molecular weight (Mw) of the resulting silsesquioxane (A-1) was 4,400.

[0154] The obtained silsesquioxane (A-1) was reprecipitated with hexane, dried, and then dissolved in dimethyl sulfoxide-d 6 Dissolve in 1H-NMR analysis revealed the following peaks: δ 12.2 ppm (broad), 6.3 ppm (s, 0.75H), 6.1 ppm (s, 0.75H), 5.9 ppm (s, 0.75H), 4.0 ppm (d, 2H), 2.5 to 2.7 ppm (m, 2H), 1.6 ppm (m, 2H), and 0.6 ppm (m, 2H). This confirmed that the compound (SH-1) had undergone quantitative Michael addition. Furthermore, Si-NMR analysis of silsesquioxane (A-1) revealed multiple peaks at -55 to -58 ppm for the T2 component (component with silanol groups) and -65 to -70 ppm for the T3 component (component without silanol groups). In this Synthesis Example 1, the component without silanol groups corresponds to either the structural unit (I) or the structural unit (II) in the above embodiment. The molar ratio of the silanol group content (SiOH content ratio) to the total content (100 mol%) of structural units (I) and (II) in silsesquioxane (A-1) determined from the intensities of the T2 and T3 components was 0.2. From these results, it was inferred that the obtained silsesquioxane (A-1) had a highly condensed cage structure as its main structure. Furthermore, from the amounts of raw materials used, the molar ratio of the structural unit (I) to which compound (SH-1) was not added and the structural unit (II) to which compound (SH-1) was added in the obtained silsesquioxane (A-1) was calculated to be 90:10.

[0155] [Synthesis Examples 2 to 16] Silsesquioxanes (A-2) to (A-16) were synthesized using the combinations shown in Table 1 in the same manner as in Synthesis Example 1. The weight-average molecular weight and silanol group content of each of the resulting silsesquioxanes were measured in the same manner as in Synthesis Example 1, and the molar ratio of structural unit (I) to structural unit (II) was calculated. The measurement results are shown in Table 1.

[0156] [Table 1]

[0157] [Comparative Synthesis Example 1] Synthesis of linear polysiloxane having acryloyl groups A 500 mL separable flask equipped with a stirrer, thermometer, nitrogen inlet tube, and reflux condenser was charged with 23.4 g (99.8 mmol) of compound (TAS-1), 211 g of 1-methoxy-2-propanol, 1.8 g of water, and 0.12 g of phosphoric acid, and stirred at 60 °C for 4 hours. After the reaction was completed, 211 g of 1-methoxy-2-propanol was added and the mixture was concentrated to 160 g. Another 211 g of 1-methoxy-2-propanol was added, and the mixture was concentrated to 75 g. 1-methoxy-2-propanol was added again, yielding a solution of acryloyl-containing polysiloxane (RS-1) with a solids concentration of 20%. Si-NMR analysis of polysiloxane (RS-1) revealed multiple peaks at -55 to -58 ppm for the T2 component and -65 to -70 ppm for the T3 component. The molar ratio of the silanol group content (SiOH content ratio) to the total content of structural units (I) and (II) in polysiloxane (RS-1), calculated from the intensities of components T2 and T3, was 1.1, suggesting that polysiloxane (RS-1) has a structure containing many linear chain structures.

[0158] [Comparative Synthesis Example 2] Michael addition to polysiloxane A 500 mL three-neck flask equipped with a thermometer and a nitrogen inlet tube was charged with 117 g of polysiloxane (RS-1) (a polycondensate of 99.8 mol of TAS-1), 1.1 g (10.4 mmol) of compound (SH-1), and 174 g of tetrahydrofuran. Then, 2.3 g (22.7 mmol) of triethylamine was slowly added and the temperature was raised to 50°C, causing gelation.

[0159] [Synthesis Example 17] Polymerization of alkali-soluble linear polysiloxane (B-1) A 500 mL separable flask equipped with a stirrer, thermometer, and reflux condenser was charged with 6.1 g (26.0 mmol) of compound (TAS-1), 13.9 g (70.0 mmol) of compound (TAS-7), 1.0 g (4.0 mmol) of compound (TAS-8), 211 g of 1-methoxy-2-propanol, 1.8 g of water, and 0.12 g of phosphoric acid, followed by stirring for 4 hours at 60° C. After completion of the reaction, 211 g of 1-methoxy-2-propanol was added and the mixture was concentrated to 160 g, and 211 g of 1-methoxy-2-propanol was added again and the mixture was concentrated to 75 g, and 1-methoxy-2-propanol was added to obtain a solution of polysiloxane (B-1) having acryloyl groups with a solids concentration of 20%. When Si-NMR of polysiloxane (B-1) was measured, multiple peaks were observed for the T2 component at -55 to -58 ppm and for the T3 component at -65 to -70 ppm. The molar ratio of the silanol group content (SiOH content ratio) to the total structural unit content of polysiloxane (B-1), calculated from the intensities of the T2 and T3 components, was 1.1. It can be inferred that polysiloxane (B-1) has a structure containing a large amount of linear structures. The weight-average molecular weight (Mw) of polysiloxane (B-1) was 1,200.

[0160] [Synthesis Example 18] Polymerization of alkali-soluble linear polysiloxane (B-2) A 500 mL separable flask equipped with a stirrer, thermometer, and reflux condenser was charged with 11.7 g (59.0 mmol) of silane compound (TAS-7), 10.7 g (41.0 mmol) of silane compound (TAS-8), 211 g of 1-methoxy-2-propanol, 1.8 g of water, and 0.12 g of phosphoric acid, and stirred at 60 °C for 4 hours. After the reaction was completed, 211 g of 1-methoxy-2-propanol was added and the mixture was concentrated to 160 g. Another 211 g of 1-methoxy-2-propanol was added, and the mixture was concentrated to 75 g. 1-methoxy-2-propanol was added again, yielding a solution of acryloyl-containing polysiloxane (B-2) with a solids concentration of 20%. Si-NMR analysis of polysiloxane (B-2) revealed multiple peaks at -55 to -58 ppm for the T2 component and -65 to -70 ppm for the T3 component. The molar ratio of the silanol group content (SiOH content ratio) to the total structural unit content of polysiloxane (B-2), calculated from the intensities of components T2 and T3, was 1.1. It can be inferred that polysiloxane (B-2) has a structure containing many linear structures. The weight-average molecular weight (Mw) of polysiloxane (B-2) was 1,400.

[0161] [Synthesis Example 19] Polymerization of alkali-soluble poly(meth)acrylic resin (B-3) A 200 mL flask equipped with a stirrer, thermometer, nitrogen inlet tube, and reflux condenser was charged with 3.8 g of acrylic acid, 9.6 g of Cyclomer M100 (Daicel Corporation), 3.2 g of phenylmaleimide, 2.6 g of styrene, and 12.8 g of methyl methacrylate dissolved in 68 g of PGMEA, 4.2 g of V-65 (Fujifilm Wako Pure Chemical Industries, Ltd.), and 0.8 g of n-dodecyl mercaptan. The mixture was heated to 70°C with stirring and then stirred for 5 hours. After the reaction was completed, the mixture was cooled to room temperature to obtain a poly(meth)acrylic resin (B-3) solution with a solids concentration of 32%. The weight-average molecular weight (Mw) of the poly(meth)acrylic resin (B-3) was 4,000.

[0162] [Synthesis Example 20] Polymerization of alkali-soluble poly(meth)acrylic resin (B-4) A 200 mL flask equipped with a stirrer, thermometer, nitrogen inlet tube, and reflux condenser was charged with 3.8 g of acrylic acid, 9.6 g of n-butyl methacrylate, 3.2 g of phenylmaleimide, 2.6 g of styrene, and 12.8 g of methyl methacrylate dissolved in 68 g of PGMEA, 4.2 g of V-65 (Fujifilm Wako Pure Chemical Industries, Ltd.), and 0.8 g of n-dodecyl mercaptan. The mixture was heated to 70°C with stirring and then stirred for 5 hours. After the reaction was completed, the mixture was cooled to room temperature to obtain a poly(meth)acrylic resin (B-4) solution with a solids concentration of 32%. The weight-average molecular weight (Mw) of the poly(meth)acrylic resin (B-4) was 4,200.

[0163] [Synthesis Example 21] Polymerization of acrylate obtained by modifying cresol novolac epoxy (meth)acrylate resin with acid anhydride and resin (B-5) having carboxylic acid group 220 parts of cresol novolac epoxy resin (manufactured by DIC Corporation, trade name: Epiclon N-695, epoxy equivalent: 220) was placed in a four-neck flask equipped with a stirrer and reflux condenser, and 214 parts of carbitol acetate was added and dissolved by heating. Next, 0.1 parts of hydroquinone as a polymerization inhibitor and 2.0 parts of dimethylbenzylamine as a reaction catalyst were added. This mixture was heated to 95-105°C, and 72 parts of acrylic acid was slowly added dropwise, allowing the reaction to proceed for 16 hours. The reaction product was cooled to 80-90°C, and 106 parts of tetrahydrophthalic anhydride was added. The reaction was allowed to proceed for 8 hours, cooled, and then removed from the flask to obtain a resin (B-5) having acrylate and carboxylic acid groups, which was obtained by modifying a cresol novolac epoxy (meth)acrylate resin with an acid anhydride (solids concentration: 50%). The solid matter of the resin (B-5) thus obtained had an acid value of 85 mgKOH / g and a weight average molecular weight (Mw) of about 3,500.

[0164] [Synthesis Example 22] Polymerization of alkali-soluble silsesquioxane resin (B-7) A silsesquioxane having a glycidoxypropyl group in the side chain was polymerized with reference to paragraphs

[0050] to

[0051] of Japanese Patent No. 4734832. During the distillation of isopropanol, an appropriate amount of PGMEA was added to achieve a solids concentration of 50% by mass. 50 g of this resin solution, 25 g of isopropanol, and 1.5 g (11.9 mmol) of compound (SH-3) were added to a 300 mL three-neck flask equipped with a thermometer and heated to 30°C while stirring. 0.2 g (0.6 mmol) of tetrabutylammonium bromide was added, heated to 50°C, and stirred for 3 hours. After the reaction was complete, the isopropanol was distilled off, transferred to a separatory funnel, and 100 mL of ethyl acetate was added. The mixture was then washed three times with 100 mL of water. Next, 50 g of PGMEA was added, and the mixture was concentrated to a volume of 50 g. Another 50 g of PGMEA was added and concentrated again. The solid content was then adjusted to 50% by mass with PGMEA to obtain a solution of silsesquioxane resin (B-7). The weight average molecular weight (Mw) of the obtained silsesquioxane resin (B-7) was 4,400.

[0165] [Synthesis Example 23] Polymerization of alkali-soluble silsesquioxane resin (B-8) A 300 mL three-neck flask equipped with a thermometer was charged with 52.5 g (210 mmol) of KBM-303 (Shin-Etsu Chemical Co., Ltd.), 50 mL of ethyl acetate, and 0.2 g (0.1 mmol) of 4-methoxyphenol, and the mixture was heated to 30°C with stirring. Subsequently, 4.8 g (47.4 mmol) of triethylamine and 12.7 g of ultrapure water were slowly added, and the mixture was heated to 60°C and stirred for 3 hours. After the reaction was completed, the mixture was transferred to a separatory funnel, 100 mL of ethyl acetate was added, and the mixture was washed once with 100 mL of 1 M aqueous hydrochloric acid and three times with 50 mL of water. Next, 80 g of PGMEA was added, and the mixture was concentrated to a liquid volume of 100 g. After that, 80 g of PGMEA was added and the mixture was concentrated again. The solids concentration was then adjusted to 50% by mass with PGMEA, yielding a silsesquioxane resin solution. 50 g of this resin solution, 25 g of isopropanol, and 1.5 g (11.9 mmol) of compound (SH-3) were added to a 300 mL three-neck flask equipped with a thermometer, and the mixture was heated to 30°C with stirring. 0.2 g (0.6 mmol) of tetrabutylammonium bromide was added, and the mixture was heated to 50°C and stirred for 3 hours. After the reaction was completed, the isopropanol was distilled off, and the mixture was transferred to a separatory funnel, to which 100 mL of ethyl acetate was added. The mixture was then washed three times with 100 mL of water. 50 g of PGMEA was then added, and the mixture was concentrated to a liquid volume of 50 g. 50 g of PGMEA was then added again, and the mixture was concentrated. The solids concentration was then adjusted to 50% by mass with PGMEA, yielding a solution of silsesquioxane resin (B-8). The weight-average molecular weight (Mw) of the resulting silsesquioxane resin (B-8) was 3600.

[0166] [Preparation Example 1] Preparation of pigment dispersion (C-1) A mixture of 12.0 parts by mass of lactam pigment [Irgaphor Black S0100CF (manufactured by B ASF Japan)] as a colorant, 11.8 parts by mass of BYK-LPN21116 (manufactured by BYK Japan, solids concentration 40.0 mass%) as a dispersant in solution, 13.0 parts by mass of alkali-soluble poly(meth)acrylic resin (B-4) as a binder in polymer solution (solids concentration 32 mass%), and 55.0 parts by mass of propylene glycol methyl ether acetate and 8 parts by mass of propylene glycol monomethyl ether as a dispersion medium was mixed and dispersed for 12 hours using a bead mill to prepare a pigment dispersion (C-1) as a colorant.

[0167] [Preparation Example 2] Preparation of pigment dispersion (C-2) A pigment dispersion (C-2) was prepared in the same manner as in Preparation Example 1 above, except that the type of colorant was changed to carbon black (TPX1227R, manufactured by Cabot Corporation).

[0168] [Preparation Example 3] Preparation of pigment dispersion (C-3) A pigment dispersion (C-3) was prepared in the same manner as in Preparation Example 1 above, except that the type of colorant was changed to a perylene pigment (Irgaphor Black FK4280, manufactured by BASF).

[0169] [Preparation Example 4] Preparation of pigment dispersion (C-4) A pigment dispersion (C-4) was prepared in the same manner as in Preparation Example 1 above, except that the type of colorant was changed to titanium black (titanium nitride, manufactured by JEMCO).

[0170] [Preparation Example 5] Preparation of pigment dispersion (C-5) A pigment dispersion (C-5) was prepared in the same manner as in Preparation Example 1, except that the type of colorant was changed to CI Pigment Green 58.

[0171] [Preparation Example 6] Preparation of pigment dispersion (C-6) A pigment dispersion (C-6) was prepared in the same manner as in Preparation Example 1 above, except that the type of colorant was changed to CI Pigment Yellow 138.

[0172] [Preparation Example 7] Preparation of pigment dispersion (C-7) A pigment dispersion (C-7) was prepared in the same manner as in Preparation Example 1 above, except that the type of colorant was changed to CI Pigment Blue 15:6.

[0173] [Preparation Example 8] Preparation of pigment dispersion (C-8) A pigment dispersion (C-8) was prepared in the same manner as in Preparation Example 1 above, except that the type of colorant was changed to CI Pigment Red 177.

[0174] [Preparation Example 9] Preparation of pigment dispersion (C-9) A pigment dispersion (C-9) was prepared in the same manner as in Preparation Example 1 above, except that 6 parts by mass of CI Pigment Blue 60 and 6 parts by mass of CI Pigment Violet 29 were used as colorants.

[0175] [Preparation Example 10] Preparation of pigment dispersion (C-10) A pigment dispersion (C-10) was prepared in the same manner as in Preparation Example 1, except that the type of colorant was changed to CI Pigment Orange 38.

[0176] <Preparation of Photosensitive Composition> The components used in preparing the photosensitive compositions of the Examples and Comparative Examples are shown below.

[0177] (Silsesquioxane (A), etc.) (A-1) to (A-16): Silsesquioxanes (A-1) to (A-16) synthesized in Synthesis Examples 1 to 16 above (RS-1): Polysiloxane (RS-1) synthesized in Comparative Synthesis Example 1 above (AC-SQ): "AC-SQ TA-100" manufactured by Toagosei Co., Ltd.

[0178] (Alkali-soluble resin (B)) (B-1) to (B-2): Linear polysiloxanes synthesized in Synthesis Examples 17 and 18 above (B-3) to (B-4): Poly(meth)acrylic resins synthesized in Synthesis Examples 19 and 20 above (B-5): A resin having an acrylate and a carboxylic acid group obtained by modifying the cresol novolac epoxy (meth)acrylate resin synthesized in Synthesis Example 21 above with an acid anhydride. (B-6): ADEKA's "WR-301" (PGMEA solution with a solid content of 44%), a resin obtained by modifying cardo resin to an acid anhydride, and a resin having acrylate and carboxylic acid groups. (B-7) to (B-8): Silsesquioxane resins synthesized in Synthesis Examples 22 and 23 above

[0179] (Color material (C)) (C-1) to (C-10): Pigment dispersions (C-1) to (C-10) obtained in Preparation Examples 1 to 10

[0180] (Radiation-sensitive radical polymerization initiator (D)) (D-1): IrgacureOXE02 (BASF Japan) (D-2): IrgacureOXE01 (BASF Japan) (D-3): an oxime initiator represented by the following formula (D-3): [ka]

[0181] (Polymerizable compound (E)) (E-1): Dipentaerythritol hexaacrylate (Tokyo Chemical Industry Co., Ltd.) (E-2): Aronix M-520 (manufactured by Toagosei Co., Ltd.) (E-3): UA-306H (Kyoeisha Chemical Co., Ltd.)

[0182] (Surfactant (F)) (F-1): Megafac F-554 (DIC)

[0183] (Solvent (G)) (G-1): Propylene glycol monomethyl ether acetate (PGMEA) (G-2): Propylene glycol monomethyl ether (PGME)

[0184] [Example 1] A colored composition was prepared by adding 24.2 parts by mass of pigment dispersion (C-1), 8.5 parts by mass of (A-1) as (A) silsesquioxane, 21.3 parts by mass of (B-3) as (B) alkali-soluble resin, 0.8 parts by mass of oxime initiator (D-1) as (D) radiation-sensitive radical polymerization initiator, 0.4 parts by mass of fluorine-based surfactant (F-1) as surfactant (F), and 44.8 parts by mass of (G-1) as solvent (G) so that the final solids content was 17.0%.

[0185] [Examples 2 to 21, Comparative Examples 1 to 4] Colored compositions of Examples 2 to 21 and Comparative Examples 1 to 4 were prepared in the same manner as in Example 1, except that the compositions were changed as shown in Table 2.

[0186] [Table 2]

[0187] [evaluation] The colored compositions prepared in Examples 1 to 21 and Comparative Examples 1 to 4 were evaluated for the following items by the methods described below. The evaluation results are shown in Table 3.

[0188] <Evaluation of resolution> Each of the prepared photosensitive coloring compositions was applied to a soda glass substrate having an ITO film formed on its surface using a spin coater, and then dried under reduced pressure at room temperature to form a coating film with a thickness of 1.5 μm. Next, using a Canon MPA-600FA, radiation containing wavelengths of 365 nm, 405 nm, and 436 nm was applied to the coating film at 35 mJ / cm through a photomask capable of forming line patterns with line widths varying in 1 μm increments in the range from 1 μm to 50 μm. 2The exposed glass substrate with the coating was then placed on the horizontal rotating table of a spin-shower developer (AD-2000 model, manufactured by Takizawa Sangyo Co., Ltd.) and puddle-developed using a 0.04% by mass potassium hydroxide aqueous solution at 23°C for 60 seconds. The developed substrate was then washed with ultrapure water, air-dried, and post-baked in a clean oven at 230°C for 30 minutes to form a line pattern. The obtained substrate with line pattern was observed with an optical microscope to determine the appearance of the formed line pattern, the presence or absence of residue, and the minimum line width that could be formed without defects in a shape corresponding to the photomask. The narrower the minimum line width, the more sufficient exposure can be achieved to the substrate side even with narrow lines, and the more a pattern with excellent adhesion to the substrate can be formed, and the higher the sensitivity during exposure (the radiation (especially g-ray, h-ray, and i-ray) transmittance of the photosensitive coloring composition used is high). (Evaluation criteria) ○: No abnormalities in appearance (cracks, etc.) and minimum line width is less than 6 μm ×: There is an abnormal appearance (cracks, etc.) or the minimum line width is 6 μm or more

[0189] <Residue evaluation> Each of the prepared photosensitive coloring compositions was applied to a soda glass substrate having an ITO film formed on its surface using a spin coater, and then dried under reduced pressure at room temperature to form a coating film with a thickness of 1.5 μm. Next, using a Canon MPA-600FA, radiation containing wavelengths of 365 nm, 405 nm, and 436 nm was applied to the coating film through a photomask at a dose of 35 mJ / cm. 2The exposed glass substrate with the coating was then placed on the horizontal rotating table of a spin-shower developer (AD-2000, manufactured by Takizawa Sangyo Co., Ltd.) and puddle-developed using a 0.04% by weight potassium hydroxide aqueous solution at 23°C for 60 seconds. The developed substrate was then rinsed with ultrapure water, air-dried, and post-baked in a clean oven at 100°C for 5 minutes, forming a rectangular hole pattern with rounded corners and measuring 5 μm in length and width. The resulting patterned substrate was then sputtered with platinum using a JEC-3000FC (manufactured by JEOL Ltd.). The interior of the hole pattern (the area removed by development) was then observed using a scanning electron microscope (S-4300, manufactured by Hitachi, Ltd.) to count the number of foreign particles (dot-like foreign particles) present therein. The evaluation criteria are as follows: The fewer foreign particles present within the pattern, the less residue there was during development, i.e., the better the developability. (Evaluation criteria) ○: The number of foreign objects inside the hole pattern is less than 5 ×: The number of foreign objects inside the hole pattern is 5 or more

[0190] <Evaluation of outgassing> The outgassing generated when the cured product of the photosensitive coloring composition obtained in the Examples and Comparative Examples was heated was measured by gas chromatography using the headspace method as shown below. First, the composition was applied to a silicon wafer substrate using a spin coater, and then dried under reduced pressure at room temperature to form a coating film with a thickness of 1.5 μm. Next, using an MPA-600FA manufactured by Canon Inc., radiation containing wavelengths of 365 nm, 405 nm, and 436 nm was applied to the coating film at 35 mJ / cm. 2 The film was exposed to light at an exposure dose of 1000 kJ / cm. This was then post-baked in a clean oven at 230°C for 30 minutes to produce a cured film. The produced cured film was cut into 1 cm square pieces, sealed in a headspace vial, and heated at 230°C for 15 minutes, and the amount of gas generated was measured by the headspace method. The amount of gas generated was evaluated based on the following criteria. (Evaluation criteria) ○: Gas generated is less than 600 ppm △: The amount of gas generated is 600 ppm or more and less than 1000 ppm ×: The gas generated is 1000 ppm or more

[0191] <Evaluation of storage stability> The viscosity of each prepared photosensitive coloring composition at 25°C was evaluated using RE85L manufactured by Toki Sangyo Co., Ltd. After storing this sample at 5°C for one week, the viscosity at 25°C was evaluated again. The viscosity increase rate of the viscosity after storage relative to the initial viscosity was calculated, and the evaluation was made based on the following criteria. (Evaluation criteria) ○: Viscosity increase rate is -5% or more, less than 5% ×: Viscosity increase rate is 5% or more

[0192] <Optical density (OD value) measurement> Each of the prepared photosensitive coloring compositions was applied using a spin coater onto a soda glass substrate having a SiO2 film formed on the surface to prevent sodium ion elution, and then dried under reduced pressure at room temperature to form a coating film with a thickness of 3.0 μm. Next, using an MPA-600FA manufactured by Canon Inc., radiation containing wavelengths of 365 nm, 405 nm, and 436 nm was applied to the resulting coating film through a photomask at a dose of 35 mJ / cm. 2 The film was exposed at an exposure dose of 1000 ppm. The exposed glass substrate with the coating was then placed on the horizontal rotating table of a spin-shower developer (AD-2000 model, manufactured by Takizawa Sangyo Co., Ltd.) and puddle-developed using a 0.04% by mass aqueous solution of potassium hydroxide at 23°C for 60 seconds. The developed substrate was then washed with ultrapure water, air-dried, and post-baked in a clean oven at 230°C for 30 minutes, forming a 2 cm x 4 cm strip pattern on the substrate. The optical density (OD value) of the obtained strip-shaped pattern was measured using a black and white transmission densitometer 361T manufactured by X-rite Co., Ltd. A higher OD value indicates a higher light-blocking property.

[0193] [Table 3]

[0194] As shown in Table 3, the photosensitive coloring compositions of Examples 1 to 21 were excellent in storage stability, and were able to form cured products excellent in resolution, residue, and outgassing. On the other hand, in the comparative examples, none of the compositions were satisfactory in all of storage stability, resolution, residue, and outgassing. [Explanation of symbols]

[0195] 1 board 2 TFT drive circuit layer 3. Light-shielding partition material (bank) 4. Light-emitting layer 5 Touch Sensor 6 Color Filters 6a Black matrix 6b Color pattern with each color (RGB) 7. Coverslip 8 Sealing Layer

Claims

1. A silsesquioxane having a structural unit (I) represented by the following formula (1): Alkali-soluble resin, Color material, a radiation-sensitive radical polymerization initiator, and Contains an organic solvent, The photosensitive coloring composition has a molar ratio of the content of silanol groups to the total content of structural units constituting the silsesquioxane of less than 0.

3. 【Chemical 1】 (In the above formula (1), X is a group represented by the following formula (2): 【Chemistry 2】 (In the above formula (2), R １ are each independently a hydrogen atom or a methyl group. ２ are each independently an alkanediyl group having 2 to 10 carbon atoms.

2. 2. The photosensitive coloring composition according to claim 1, comprising a silsesquioxane having a structural unit (II) represented by the following formula (3) in addition to the structural unit (I) represented by the above formula (1): 【Chemistry 3】 (In the above formula (3), Y is represented by the following formula (4a), formula (4b), or formula (4c).) 【Chemistry 4】 (In the above formulas (4a), (4b), and (4c), R １ are each independently a hydrogen atom or a methyl group. ２ are each independently an alkanediyl group having 2 to 10 carbon atoms. ３ is a divalent organic group. ４ is a single bond or a divalent organic group. X is a halogen atom, a hydroxy group, a carboxy group, a cyano group, a nitro group, an alkyl group, or an alkoxy group. n is an integer of 0 to 4. When n is 2 or more, multiple Xs may be the same or different. * indicates a bonding site.

3. 3. The photosensitive coloring composition according to claim 2, wherein the content of the structural unit (I) relative to the total content of the structural unit (I) and the structural unit (II) in the silsesquioxane is 10 mol % or more and 100 mol % or less.

4. The photosensitive coloring composition according to claim 1, further comprising a polymerizable compound having two or more polymerizable groups.

5. A cured product obtained by curing the photosensitive coloring composition according to any one of claims 1 to 4.

6. The cured product according to claim 5, having an optical density (OD value) in the range of 0.5 to 4.

0.

7. The cured product according to claim 5, which is a color filter, a black matrix, or a light-shielding partition wall material.

8. An image display panel comprising the cured product according to claim 5 as a color pattern of a color filter.

9. An image display device comprising the image display panel according to claim 8.

10. A color filter comprising the cured product according to claim 5 as a black matrix.

11. An image display panel comprising the color filter according to claim 10.

12. An image display device comprising the image display panel according to claim 11.

13. An image display device comprising the cured product according to claim 5 as a light-shielding partition wall material.

14. A step of applying the photosensitive coloring composition according to any one of claims 1 to 4 onto a substrate to form a coating film; site-selectively exposing the coating to light; developing the exposed coating; heating the developed patterned coating; A method for producing a patterned cured product, comprising:

15. The method according to claim 14, wherein the patterned cured product is a color filter, a black matrix, or a light-shielding partition wall material.

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