Curable composition

Abstract

To provide a curable composition containing a light scattering agent which is curable at low temperature, and can improve hardness of a cured film obtained by curing the curable composition at low temperature.SOLUTION: A curable composition contains a light scattering agent (B) and a resin (C) and contains no semiconductor particles (A), wherein a value X calculated by the following expression (1) from the acid value of the resin (C) and a weight average molecular weight Mw is 10 or more and 59.75 or less, and a double bond equivalent of the resin (C) is 100 g / eq or more and less than 500 g / eq. Expression (1): X={acid value (mg-KOH / g)×weight average molecular weight Mw} / 10,000.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a curable composition containing a light-scattering agent.

Background Art

[0002] Patent Document 1 discloses that a curable composition containing a light-scattering agent (A) and a photopolymerizable compound (B) is dried at 100°C for 3 minutes (pre-bake) to form a film, and then an exposure process is carried out by irradiating light. After development, a heat-curing process is carried out by performing a heat-curing treatment (post-bake) at 80°C to 230°C for 1 hour, and a cured film having a Martens hardness of 0.10 GPa or more is obtained.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] A curable composition containing a light-scattering agent is preferable if it can be cured at a low temperature because it can reduce energy costs. Also, a certain degree of hardness is required for the obtained cured film to be used in a display device or the like.

[0005] Therefore, an object of the present invention is to provide a curable composition containing a light-scattering agent that can be cured at a low temperature and can provide a cured film having good hardness when cured at a low temperature.

Means for Solving the Problems

[0006] The present invention that has achieved the above problems is as follows. [1] A curable composition containing a light-scattering agent (B) and a resin (C) and not containing semiconductor particles (A), The value X calculated by the following formula (1) from the acid value and weight average molecular weight Mw of the resin (C) is 10 or more and 59.75 or less, A curable composition in which the double bond equivalent of the resin (C) is 100 g / eq or more and less than 500 g / eq. X = {acid value (mg-KOH / g) × weight average molecular weight Mw} / 10,000 …(1) [2] The curable composition according to [1], wherein the mass ratio (C / B) of the resin (C) to the light scattering agent (B) is 10 or more. [3] The curable composition according to [1] or [2], wherein the acid value of the resin (C) is less than 80 mg-KOH / g. [4] The curable composition according to any one of [1] to [3], wherein the weight average molecular weight Mw of the resin (C) is 4930 or more and 8000 or less. [5] The curable composition according to any one of [1] to [4], further comprising a polymerizable compound (D), wherein the mass ratio (C / D) of the resin (C) to the polymerizable compound (D) is 2 or more. [6] The curable composition according to any one of [1] to [5], further comprising a polymerizable compound (D), wherein the polymerizable compound (D) includes a polymerizable compound having one or more cyclic hydrocarbon groups and two ethylenically unsaturated bonds in one molecule. [7] The curable composition according to [6], wherein the polymerizable compound (D) further includes a polymerizable compound having an acidic functional group and three or more ethylenically unsaturated bonds in one molecule. [8] The curable composition according to any one of [1] to [7], which does not contain a colored colorant (K).

Advantages of the Invention

[0007] According to the present invention, a curable composition containing a light scattering agent can be cured at a low temperature, and the hardness of a cured film obtained by curing at a low temperature can be made good.

Embodiments for Carrying Out the Invention

[0008] <<Curable Composition>> The curable composition preferably contains at least one selected from a polymerizable compound (D), a polymerization initiator (E), a light stabilizer (F), a leveling agent (H), and a solvent (J), in addition to a light scattering agent (B) and a resin (C). Also, the curable composition does not contain semiconductor particles (A) such as quantum dots that absorb primary light and emit light with a wavelength different from that of the primary light. Further, the curable composition preferably does not contain a colored colorant (K) such as a pigment or a dye. For both the semiconductor particles (A) and the colored colorant (K), "not containing" means that the amount in the curable composition is less than 1% by mass (including 0% by mass). By not containing the semiconductor particles (A) and the colored colorant (K), the hardness of the obtained cured film can be increased.

[0009] In this specification, the compounds exemplified as each component can be used alone or in combination of two or more, unless otherwise specified. Also, when using a plurality of types of each component, the content can be adjusted as the total amount of the plurality of types, unless otherwise specified.

[0010] <Light Scattering Agent (B)> The cured film formed from the curable composition containing the light scattering agent (B) can scatter and emit light having the same or almost the same wavelength as the light incident on the cured film. Also, by incorporating the light scattering agent (B) into the cured film, the light transmittance and viewing angle characteristics of the cured film can be controlled, or the emitted light intensity of the cured film can be improved.

[0011] Examples of the light scattering agent (B) include inorganic particles such as metal or metal oxide particles and glass particles. Since it is preferable to have only a scattering effect without absorption due to coloring, it is preferably metal oxide particles. Examples of the metal oxide include TiO2, SiO2, BaTiO3, ZnO, etc., and TiO2 particles are preferably used because they efficiently scatter light. Generally, since the above inorganic particles are difficult to disperse in a solvent as they are, a dispersant described later is usually used. The light scattering agent (B) may contain two or more types of particles.

[0012] The average particle diameter of the light-scattering agent (B) is, for example, about 0.03 μm or more and 20 μm or less, and from the viewpoint of enhancing the light-scattering ability and the dispersibility in the curable composition, it is preferably 0.05 μm or more and 1 μm or less, more preferably 0.05 μm or more and 0.5 μm or less, and still more preferably 0.05 μm or more and 0.35 μm or less. The average particle diameter of the light-scattering agent (B) can be measured as the volume-based median diameter (D50) by measuring the particle diameter distribution using a centrifugal sedimentation type dispersion stability particle diameter distribution apparatus.

[0013] As the light-scattering agent (B), those in which the light-scattering agent is previously dispersed in part or all of the solvent (J) using the dispersant (I) may be used. As the dispersant (I), commercially available products can be used. Examples of commercially available products include DISPERBYK-101, 102, 103, 106, 107, 108, 109, 110, 111, 116, 118, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 192, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155; ANTI-TERRA-U, U100, 203, 204, 250; BYK-P104, P104S, P105, 220S, 6919; BYK-LPN6919, 21116; LACTIMON, LACTIMON-WS; Bykumen, etc. manufactured by BYK Chemie Japan Co., Ltd.; SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc. manufactured by Lubrizol Japan Ltd.; EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc. manufactured by BASF; Examples include Ajisper PA111, PB711, PB821, PB822, PB824, etc. manufactured by Ajinomoto Fine-Techno Co., Inc.

[0014] The content of the light-scattering agent (B) in the curable composition is, for example, 0.001% by mass or more and 50% by mass or less with respect to the total amount of the solid content of the curable composition. From the viewpoints of the developability of the cured film, enhancing the light-scattering ability, and improving the emitted light intensity of the cured film, it is preferably 0.5% by mass or more and 30% by mass or less, more preferably 1% by mass or more and 10% by mass or less, and even more preferably 2% by mass or more and 7% by mass or less.

[0015] In this specification, the total amount of the solid content in the composition means the total of the components contained in the composition excluding the solvent (J). The content in the solid content of the composition can be measured by known analytical means such as liquid chromatography or gas chromatography. The content of each component in the solid content of the composition may be calculated from the formulation at the time of preparing the composition.

[0016] <Resin (C)> Examples of the resin (C) include the following resins [K1] to [K6], etc.

[0017] Resin [K1]; a copolymer having a structural unit derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter also referred to as "(a)"), and a structural unit derived from a monomer (c) copolymerizable with (a) (however, different from (a)) (hereinafter also referred to as "(c)"); Resin [K2]; a copolymer having a structural unit derived from the above (a), a structural unit derived from the above (c), and a structural unit derived from a monomer (b) (hereinafter also referred to as "(b)") having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K3]; a copolymer having a structural unit obtained by adding the above (b) to the structural unit derived from the above (a) and a structural unit derived from the above (c); Resin [K4]: a copolymer having a structural unit obtained by adding the above (b) to the structural unit derived from the above (a) and further subjecting a carboxylic anhydride to an ester bond, and a structural unit derived from the above (c). Resin [K5]; a copolymer having a structural unit obtained by adding the above (a) to the structural unit derived from the above (b) and a structural unit derived from the above (c); Resin [K6]; a copolymer having a structural unit obtained by adding the above (a) to the structural unit derived from the above (b) and further subjecting a carboxylic anhydride to an ester bond, and a structural unit derived from the above (c).

[0018] Examples of (a) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic acid; bicyclic unsaturated compounds containing a carboxy group such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of polyvalent carboxylic acids with a valence of 2 or more, such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl]; Unsaturated (meth)acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)(meth)acrylic acid etc. can be mentioned.

[0019] Among these, from the viewpoints of copolymerization reactivity and the like, (meth)acrylic acid, succinic acid mono[2-(meth)acryloyloxyethyl], maleic anhydride, etc. are preferable.

[0020] In this specification, (meth)acrylic acid means acrylic acid and / or methacrylic acid. The same applies to "(meth)acryloyl", "(meth)acrylate", etc.

[0021] (b) is, for example, a monomer having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0022] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc.

[0023] (b1) includes, for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)"), and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

[0024] (b1-1) includes, for example, glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.

[0025] (b1-2) includes vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), a compound represented by formula (BI), and a compound represented by formula (BII), etc.

[0026] [Chemical formula]

[0027] [In formulas (BI) and (BII), R e and R f each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X e and X f each represents a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O. ]

[0028] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of the alkyl group in which the hydrogen atom is substituted with hydroxy include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R e and R f are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0029] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X e and X fExamples thereof preferably include a single bond, a methylene group, an ethylene group, *-CH2-O- and *-CH2CH2-O-, more preferably a single bond and *-CH2CH2-O- (* represents a bond to O).

[0030] Examples of the compound represented by formula (BI) include compounds represented by any of formula (BI-1) to formula (BI-15). Among them, compounds represented by formula (BI-1), formula (BI-3), formula (BII-5), formula (BI-7), formula (BI-9) or formula (BI-11) to formula (BI-15) are preferred, and compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15) are more preferred.

[0031]

Chemical formula

[0032] Examples of the compound represented by formula (BII) include compounds represented by any of formula (BII-1) to formula (BII-15). Among them, compounds represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) or formula (BII-11) to formula (BII-15) are preferred, and compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15) are more preferred.

[0033]

Chemical formula

[0034] The compound represented by formula (BI) and the compound represented by formula (BII) may each be used alone or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, their content ratios [compound represented by formula (BI): compound represented by formula (BII)] are preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0035] (b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane and the like.

[0036] (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

[0037] (b) is preferably (b1) in terms of being able to further enhance the reliability such as chemical resistance.

[0038] Since the reactivity during the production of resins [K3] to [K6] is high and unreacted (b) is less likely to remain, (b) is preferably a monomer having an oxirane ring and an ethylenically unsaturated bond.

[0039] (c) includes, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6Decan-8-yl (meth)acrylate (in the art, it is commonly known as "dicyclopentanyl (meth)acrylate". It may also be referred to as "tricyclodecyl (meth)acrylate".), tricyclo[5.2.1.0 2,6 Decen-8-yl (meth)acrylate (in the art, it is commonly known as "dicyclopentenyl (meth)acrylate".), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate and other (meth)acrylic acid esters; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimidyl 4-maleimidobutyrate, N-succinimidyl 6-maleimidocaproate, N-succinimidyl 3-maleimidopropionate, N-(9-acridinyl)maleimide; Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene etc. can be mentioned.

[0040] Among the above, from the viewpoint of copolymerization reactivity, methyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are preferable.

[0041] In resin [K1], the ratio of the structural units derived from each is among all the structural units constituting resin [K1], (a) the structural unit derived from; 2 mol% or more and 60 mol% or less (c) the structural unit derived from; 40 mol% or more and 98 mol% or less it is preferably that, (a) the structural unit derived from; 10 mol% or more and 50 mol% or less (c) the structural unit derived from; 50 mol% or more and 90 mol% or less it is more preferably that.

[0042] When the ratio of the structural units of resin [K1] is within the above range, it tends to be excellent in storage stability and solvent resistance.

[0043] Resin [K1] can be produced, for example, with reference to the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Publishing Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references described in the literature.

[0044] Specifically, a method includes putting predetermined amounts of (a) and (c), a polymerization initiator, a solvent, etc. into a reaction vessel, replacing oxygen with nitrogen, for example, to create a deoxygenated atmosphere, and heating and maintaining the temperature while stirring.

[0045] The polymerization initiator, solvent, etc. used are not particularly limited, and those commonly used in the art can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.) can be mentioned. As the solvent, any one that can dissolve each monomer may be used, and examples include the solvents described later as solvent (J).

[0046] The obtained copolymer may be used as the reaction solution as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used. If the solvent (J) described later is used as the solvent during polymerization, the reaction solution can be used as it is for the preparation of the composition, so the manufacturing process of the composition can be simplified.

[0047] In resin [K2], the ratio of the structural units derived from each is among all the structural units constituting resin [K2], Structural unit derived from (a); 2 to 45 mol% Structural unit derived from (b); 2 to 95 mol% Structural unit derived from (c); 1 to 65 mol% It is preferably such that, Structural unit derived from (a); 5 to 40 mol% Structural unit derived from (b); 5 to 80 mol% Structural unit derived from (c); 5 to 60 mol% It is more preferably such that.

[0048] When the ratio of the structural units of resin [K2] is within the above range, the storage stability of the curable composition and the developability when forming a coloring pattern tend to be excellent.

[0049] Resin [K2] can be produced, for example, in the same manner as the method described as the production method of resin [K1].

[0050] Resin [K3] can be produced by adding the cyclic ether having 2 to 4 carbon atoms of (b) to the copolymer of (a) and (c) in the carboxylic acid and / or carboxylic anhydride having (a).

[0051] First, a copolymer of (a) and (c) is produced in the same manner as the method described as the production method of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as the ratio described for resin [K1].

[0052] Next, a cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer.

[0053] Subsequent to the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and in the presence of (b), a carboxylic acid or carboxylic anhydride, a reaction catalyst for the cyclic ether (for example, an organic phosphorus compound, a metal complex, an amine compound, etc.) and a polymerization inhibitor (for example, hydroquinone, methoxyquinone, etc.), etc., for example, at 60 ° C or higher and 130 ° C or lower, and by reacting for 1 hour or more and 10 hours or less, resin [K3] can be produced.

[0054] The usage amount of (b) is preferably 5 mol or more and 80 mol or less, more preferably 10 mol or more and 75 mol or less, per 100 mol of (a). By setting it within this range, the curable composition can be cured at a low temperature, and the hardness of the obtained cured film can be made good.

[0055] Examples of the organic phosphorus compound as the reaction catalyst include triphenylphosphine and the like. Examples of the amine compound as the reaction catalyst include aliphatic tertiary amine compounds or aliphatic quaternary ammonium salt compounds, etc., and specific examples thereof include tris(dimethylaminomethyl)phenol, triethylamine, tetrabutylammonium bromide, tetrabutylammonium chloride, etc. The reaction catalyst is preferably an organic phosphorus compound.

[0056] The usage amount of the reaction catalyst is preferably 0.001 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the total amount of (a), (b), and (c).

[0057] The usage amount of the polymerization inhibitor is preferably 0.001 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the total amount of (a), (b), and (c).

[0058] Reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of the manufacturing equipment, the heat generation amount due to polymerization, etc. Note that, similar to the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the manufacturing equipment, the heat generation amount due to polymerization, etc.

[0059] As the first step, the resin [K5] obtains a copolymer of (b) and (c) in the same manner as the manufacturing method of the resin [K1] described above. Similar to the above, the obtained copolymer may be used as the solution after the reaction as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used.

[0060] (b) and the ratio of the structural unit derived from (c) are respectively (b) the structural unit derived from; 5 mol% or more and 95 mol% or less (c) the structural unit derived from; 5 mol% or more and 95 mol% or less It is preferably that (b) the structural unit derived from; 10 mol% or more and 90 mol% or less Structural units derived from (c); 10 mol% or more and 90 mol% or less is more preferably.

[0061] Resin [K4] is a resin obtained by further reacting resin [K3] with a carboxylic anhydride. The carboxylic anhydride is reacted with the hydroxy group generated by the reaction of a carboxylic acid or carboxylic anhydride with a cyclic ether. Examples of the carboxylic anhydride include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like. The amount of the carboxylic anhydride used is preferably 0.5 mol or more and 1 mol or less per 1 mol of the amount of (b) used.

[0062] Resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride of (a) with the cyclic ether derived from (b) in the copolymer of (b) and (c) under the same conditions as the production method of resin [K3].

[0063] The amount of (a) used for reacting with the copolymer is preferably 5 mol or more and 120 mol or less, more preferably 20 mol or more and 110 mol or less, per 100 mol of (b).

[0064] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic anhydride. The carboxylic anhydride is reacted with the hydroxy group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic anhydride.

[0065] Examples of the carboxylic acid anhydride include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like.

[0066] The amount of the carboxylic acid anhydride used is preferably 0.05 to 1 mol, more preferably 0.1 to 0.8 mol, and still more preferably 0.15 to 0.6 mol, per 1 mol of the amount of (a) used.

[0067] Examples of the resins [K1], [K2], [K3], [K4], [K5] and [K6] include resin [K1] such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, (meth)acrylic acid / succinic acid mono[2-(meth)acryloyloxyethyl] / dicyclopentanyl (meth)acrylate / methyl (meth)acrylate copolymer; resin [K2] such as glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / methyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer; Resins such as a resin obtained by adding glycidyl (meth)acrylate to a benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, and a resin obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K3]; Resins such as a resin obtained by further ester-bonding tetrahydrophthalic anhydride or succinic anhydride to a resin obtained by adding glycidyl (meth)acrylate to a dicyclopentanyl (meth)acrylate / methyl (meth)acrylate / (meth)acrylic acid copolymer, and a resin obtained by further ester-bonding tetrahydrophthalic anhydride or succinic anhydride to a resin obtained by adding glycidyl (meth)acrylate to a dicyclopentanyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; Resins such as a resin obtained by adding (meth)acrylic acid to a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, and a resin obtained by adding (meth)acrylic acid to a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate [K5]; Examples thereof include resins such as a resin obtained by further ester-bonding tetrahydrophthalic anhydride or succinic anhydride to a resin obtained by adding (meth)acrylic acid to a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, and a resin obtained by further ester-bonding tetrahydrophthalic anhydride or succinic anhydride to a resin obtained by adding (meth)acrylic acid to a copolymer of dicyclopentanyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate [K6], etc.

[0068] The resin (C) contained in the curable composition preferably contains at least one selected from the group consisting of resin [K1], resin [K2], resin [K3], resin [K4], resin [K5], and resin [K6], more preferably contains at least one selected from the group consisting of resin [K3], resin [K4], resin [K5], and resin [K6], still more preferably contains at least one selected from the group consisting of resin [K4] and resin [K6], and particularly preferably resin [K6].

[0069] As a further example of the resin (C), the resin described in JP-A-2018-123274 can be mentioned. As the resin, a polymer having a double bond in the side chain and containing a structural unit (α) represented by the following formula (I) and a structural unit (β) represented by the following formula (II) in the main chain and further containing an acid group (hereinafter, also referred to as "resin (Ca)") can be mentioned.

[0070] The acid group can be introduced into the resin, for example, when the resin (Ca) contains a structural unit (γ) derived from an acid group-containing monomer (for example, (meth)acrylic acid, etc.). The resin (Ca) preferably contains the structural units (α), (β), and (γ) in the main chain skeleton.

[0071] [Chemical formula]

[0072] [In the formula, R A and R B each independently represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms. n represents the average number of repeating units of the structural unit represented by formula (I) and is a number of 1 or more.]

[0073] [Chemical formula]

[0074] [In the formula, R C each independently represents a hydrogen atom or a methyl group. R Dindependently represents a linear or branched hydrocarbon group having 4 to 20 carbon atoms. m represents the average number of repeating units of the structural unit represented by formula (II), and is a number of 1 or more. In the resin (Ca), from the viewpoint of the storage stability of the resin (Ca), the content ratio of the structural unit (α) is, for example, 0.5% by mass or more and 50% by mass or less, preferably 1% by mass or more and 40% by mass or less, more preferably 5% by mass or more and 30% by mass or less, based on 100% by mass of the total amount of all monomer units that give the main chain skeleton of the resin (Ca). n in formula (I) represents the average number of repeating units of the structural unit (α) in the resin (Ca), and n can be set so that the content ratio of the structural unit (α) is within the above range.

[0075] From the viewpoint of solvent resistance, the content ratio of the structural unit (β) is, for example, 10% by mass or more and 90% by mass or less, preferably 20% by mass or more and 80% by mass or less, more preferably 30% by mass or more and 75% by mass or less, based on 100% by mass of the total amount of all monomer units that give the main chain skeleton of the resin (Ca). m in formula (II) represents the average number of repeating units of the structural unit (β) in the resin (Ca), and m can be set so that the content ratio of the structural unit (β) is within the above-mentioned range.

[0076] From the viewpoint of the solubility of the resin (Ca) in the solvent (J) and the like, the content ratio of the structural unit (γ) is, for example, 0.5% by mass or more and 50% by mass or less, preferably 2% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 45% by mass or less, based on 100% by mass of the total amount of all monomer units that give the main chain skeleton of the resin (Ca).

[0077] In the present invention, it is important that the value X calculated by the following formula (1) from the acid value and the weight average molecular weight Mw of the resin (C) is 10 or more and 59.75 or less. By setting the value X within this range, the curable composition can be cured at a low temperature, and the hardness of the resulting cured film can be made good. Further, since the value X is 59.75 or less, it is also possible to ensure the development residual film ratio of the cured product when cured at a low temperature (for example, the ratio of the film thickness t1 when the curable composition is pre-baked, exposed, developed, and post-baked at a low temperature to the film thickness t0 when pre-baked, exposed, and post-baked at a low temperature: t1 / t0). The value X is preferably 13.75 or more, more preferably 16.50 or more, and preferably 56.25 or less, more preferably 30.00 or less. The value X is preferably 13.75 or more and 56.25 or less, and more preferably 16.50 or more and 30.00 or less. X = {acid value (mg-KOH / g) × weight average molecular weight Mw} / 10,000 …(1)

[0078] The acid value of the resin (C) is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (C), and can be determined, for example, by titration using an aqueous potassium hydroxide solution. Specifically, it can be measured according to the measurement method described in the Examples section below. Alternatively, for the resin (C) contained in the composition, the acid value may be determined, for example, by performing its structural analysis.

[0079] The weight average molecular weight Mw of the resin (C) is the weight average molecular weight in terms of standard polystyrene measured by GPC, and can be measured according to the measurement method described in the Examples section below. Alternatively, for the resin (C) contained in the curable composition, Mw may be measured using GPC.

[0080] The weight average molecular weight Mw of the resin (C) is not particularly limited as long as it can satisfy the above-mentioned value X. For example, it is 1,000 or more, preferably 3,000 or more, more preferably 4,930 or more, still more preferably 5,000 or more, even more preferably 5,500 or more. Also, for example, it is 100,000 or less, preferably 50,000 or less, more preferably 20,000 or less, still more preferably 8,000 or less, even more preferably 7,500 or less. The weight average molecular weight Mw of the resin (C) is preferably 4,930 or more and 8,000 or less, more preferably 5,000 or more and 8,000 or less, still more preferably 5,500 or more and 7,500 or less. The Mw of the resin (C) can be adjusted by appropriately combining reaction conditions such as the selection of raw materials used, the charging method, the reaction temperature, and the reaction time.

[0081] The acid value of the resin (C) is not particularly limited as long as it can satisfy the above-mentioned value X. However, it is preferably 150 mg-KOH / g or less, more preferably 110 mg-KOH / g or less, still more preferably less than 80 mg-KOH / g, even more preferably 75 mg-KOH / g or less, particularly preferably 40 mg-KOH / g or less. Also, it is preferably 20 mg-KOH / g or more, more preferably 25 mg-KOH / g or more, still more preferably 30 mg-KOH / g or more. The acid value of the resin (C) is preferably 25 mg-KOH / g or more and less than 80 mg-KOH / g, more preferably 25 mg-KOH / g or more and 75 mg-KOH / g or less, still more preferably 30 mg-KOH / g or more and 40 mg-KOH / g or less. The acid value of the resin (C) can be adjusted by the content of the monomer component having an acid group (for example, the above (a)) and the content of the carboxylic acid anhydride.

[0082] Also, it is important that the double bond equivalent of the resin (C) is 100 g / eq or more and less than 500 g / eq. When the double bond equivalent is within the above range, the curable composition can be cured at a low temperature, and the hardness of the resulting cured film can be made good. The double bond equivalent of the resin (C) is preferably 200 g / eq or more, more preferably 250 g / eq or more, still more preferably 300 g / eq or more, and preferably 450 g / eq or less, more preferably 400 g / eq or less. The double bond equivalent of the resin (C) is preferably 250 g / eq or more and 450 g / eq or less, more preferably 300 g / eq or more and 400 g / eq or less. Examples of the resin having the above-described double bond equivalent include (meth)acrylic resins. The resin (C) preferably consists of a (meth)acrylic resin.

[0083] The content of the resin (C) in the curable composition is, for example, 5% by mass or more and 80% by mass or less, preferably 20% by mass or more and 75% by mass or less, more preferably 35% by mass or more and 73% by mass or less, still more preferably 40% by mass or more and 70% by mass or less, based on the total amount of the solid content of the curable composition. When the content of the resin (C) is within the above range, the curable composition can be cured at a low temperature, and the hardness of the resulting cured film can be made good.

[0084] The mass ratio (C / B) of the resin (C) to the light scattering agent (B) is preferably 10 or more, more preferably 16 or more, still more preferably 18 or more, even more preferably 20 or more, and the upper limit is not particularly limited, but may be 35 or less. When the mass ratio (C / B) of the resin (C) to the light scattering agent (B) is within the above range, the light scattering agent (B) is easily dispersed.

[0085] <Polymerizable compound (D)> The polymerizable compound (D) is a compound that can be polymerized by active radicals, acids, etc. generated from a polymerization initiator (E) described later. Examples of the polymerizable compound (D) include photopolymerizable compounds such as compounds having an ethylenically unsaturated bond, for example, (meth)acrylate compounds. Another example of the polymerizable compound (D) is a thermopolymerizable compound. The curable composition may contain two or more kinds of the polymerizable compound (D).

[0086] Examples of the polymerizable compound (D) include a photopolymerizable compound (Dα) having two ethylenically unsaturated bonds in the molecule and a photopolymerizable compound (Dβ) having three or more ethylenically unsaturated bonds in the molecule. In the photopolymerizable compound (Dβ), the number of ethylenically unsaturated bonds in the molecule is preferably 6 or less. The ethylenically unsaturated bond is preferably a (meth)acryloyloxy group. The weight average molecular weight of the polymerizable compound (D) is preferably 150 or more and 2900 or less, more preferably 250 or more and 1500 or less. The polymerizable compound (D) preferably contains one or more selected from the photopolymerizable compound (Dα) and the photopolymerizable compound (Dβ), and more preferably contains one or more of the photopolymerizable compound (Dβ). It is also preferable that the photopolymerizable compound (D) contains one or more of the photopolymerizable compound (Dα) and one or more of the photopolymerizable compound (Dβ).

[0087] Examples of the photopolymerizable compound (Dα) having two ethylenically unsaturated bonds in the molecule include difunctional (meth)acrylic compounds, such as alkylene glycol di(meth)acrylate, polyoxyalkylene glycol di(meth)acrylate, halogen-substituted alkylene glycol di(meth)acrylate, di(meth)acrylate of aliphatic polyol, di(meth)acrylate of hydrogenated dicyclopentadiene or tricyclodecane dialkanol, di(meth)acrylate of dioxane glycol or dioxane dialkanol, di(meth)acrylate of an alkylene oxide adduct of bisphenol A or bisphenol F, epoxy di(meth)acrylate of bisphenol A or bisphenol F, and the like.

[0088] More specific examples of the above bifunctional (meth)acrylic compounds include ethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol di(meth)acrylate, ditrimethylolpropane di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, di(meth)acrylate of hydroxypivalic acid neopentyl glycol ester, 2,2-bis[4-(meth)acryloyloxyethoxyethoxyphenyl]propane, 2,2-bis[4-(meth)acryloyloxyethoxyethoxycyclohexyl]propane, hydrogenated dicyclopentadienyl di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, 1,3-dioxane-2,5-diyl di(meth)acrylate [alias: dioxane glycol di(meth)acrylate], di(meth)acrylate of an acetal compound of hydroxypivalaldehyde and trimethylolpropane [chemical name: 2-(2-hydroxy-1,1-dimethylethyl)-5-ethyl-5-hydroxymethyl-1,3-dioxane], tris(hydroxyethyl)isocyanurate di(meth)acrylate, di(meth)acrylate of ethoxylated bisphenol A, di(meth)acrylate of propoxylated bisphenol A, di(meth)acrylate of ethoxylated bisphenol F, di(meth)acrylate of propoxylated bisphenol F, and the like.

[0089] The photopolymerizable compound (Dα) having two ethylenically unsaturated bonds in the molecule is preferably a photopolymerizable compound (Dα1) having one or more cyclic hydrocarbon groups and two ethylenically unsaturated bonds in one molecule, and it is preferable that the polymerizable compound (D) contains one or more of the photopolymerizable compounds (Dα1). In the photopolymerizable compound (Dα1), the cyclic hydrocarbon group is preferably an aromatic hydrocarbon group, and the aromatic hydrocarbon group is more preferably a phenylene group. Also, in the photopolymerizable compound (Dα1), the number of cyclic hydrocarbon groups in one molecule is preferably two. Specific examples of the photopolymerizable compound (Dα1) include di(meth)acrylates of ethoxylated bisphenol A, di(meth)acrylates of propoxylated bisphenol A, di(meth)acrylates of ethoxylated bisphenol F, di(meth)acrylates of propoxylated bisphenol F, and the like.

[0090] Examples of the polymerizable compound (Dβ) having three or more ethylenically unsaturated bonds in the molecule include a compound (Dβ1) having three or more ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) in the molecule and having an acidic functional group, and a compound (Dβ2) having three or more ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) in the molecule and not having an acidic functional group. The polymerizable compound (D) preferably contains at least one of the compounds (Dβ1) and (Dβ2), and more preferably contains at least one of the compounds (Dβ1). Examples of the above acidic functional group include a carboxy group, a sulfonic acid group, a phosphoric acid group, and the like. Among them, the acidic functional group is preferably a carboxy group.

[0091] The number of ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) in one molecule of the compound (Dβ1) is, for example, 3 or more and 6 or less, preferably 3 or more and 5 or less, and more preferably 3. The number of acidic functional groups in one molecule of the compound (Dβ1) is 1 or more, and preferably 1. When having two or more acidic functional groups, each acidic functional group may be different or the same, but it preferably has at least one carboxy group.

[0092] Examples of the compound (Dβ1) include compounds obtained by esterifying a compound having three or more (meth)acryloyloxy groups and hydroxy groups such as pentaerythritol tri(meth)acrylate or dipentaerythritol penta(meth)acrylate with a dicarboxylic acid or a dicarboxylic anhydride. Examples of such compounds include a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and succinic acid, a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate and succinic acid, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and maleic acid, and a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate and maleic acid. Among them, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and succinic acid is preferred.

[0093] Examples of commercially available products of the compound (Dβ1) include "Aronix M-510" manufactured by Toagosei Co., Ltd., which has a dibasic acid anhydride adduct of pentaerythritol tri(meth)acrylate as a main component, and "Aronix M-520D" manufactured by Toagosei Co., Ltd., which has a dibasic acid anhydride adduct of dipentaerythritol penta(meth)acrylate as a main component. These commercially available products have a carboxy group as an acidic functional group.

[0094] The number of ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) possessed by the compound (Dβ2) is preferably 3 to 6, more preferably 4 to 6.

[0095] Examples of the compound (Dβ2) include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, and the like. Among them, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and the like are preferable.

[0096] The polymerizable compound (D) in the curable composition preferably contains the compound (Dα) (particularly the compound (Dα1)) because the curable composition can be cured at a low temperature, the hardness of the resulting cured film can be made good, and furthermore, the residue after development of the curable composition can be reduced. The curable composition preferably contains the compound (Dβ) because the curable composition can be cured at a low temperature, the hardness of the resulting cured film can be made good, the curability during exposure and the patterning property during development can be made good, and furthermore, the dispersibility of the light scattering agent (B) can be improved, whereby the emitted light intensity of the cured film can be improved.

[0097] In 100% by mass of the polymerizable compound (D) contained in the curable composition, the compound (Dα) (particularly the compound (Dα1)) is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, and may be 70% by mass or less. In 100% by mass of the polymerizable compound (D) contained in the curable composition, the compound (Dβ) is preferably 20% by mass or more, more preferably 30% by mass or more, still more preferably 40% by mass or more, may be 100% by mass, or may be 60% by mass or less.

[0098] When the polymerizable compound (D) in the curable composition contains both the compound (Dα) and the compound (Dβ), it preferably contains the compounds (Dα1) and (Dβ1). The total content of the compounds (Dα1) and (Dβ1) with respect to 100% by mass of the polymerizable compound (D) is preferably 70% by mass or more, more preferably 85% by mass or more, and may be 100% by mass. The content of the compound (Dα1) with respect to 100% by mass of the total amount of the compounds (Dα1) and (Dβ1) is preferably more than 50% by mass, more preferably 53% by mass or more, still more preferably 55% by mass or more, and may be 70% by mass or less.

[0099] When the polymerizable compound (D) in the curable composition contains both the compound (Dβ1) and the compound (Dβ2), the total content of the compounds (Dβ1) and (Dβ2) with respect to 100% by mass of the polymerizable compound (D) is preferably 70% by mass or more, more preferably 85% by mass or more, and may be 100% by mass. The content of the compound (Dβ2) with respect to 100% by mass of the total amount of the compounds (Dβ1) and (Dβ2) is preferably more than 50% by mass, more preferably 53% by mass or more, still more preferably 55% by mass or more, and may be 70% by mass or less.

[0100] The content ratio (total amount in the case of multiple types) of the polymerizable compound (D) in the curable composition is preferably 3% by mass or more and 40% by mass or less, more preferably 8% by mass or more and 30% by mass or less, still more preferably 10% by mass or more and 25% by mass or less, based on 100% by mass of the total solid content of the curable composition. When the content ratio of the polymerizable compound (D) is within the above range, the curable composition can be cured at a low temperature, and the hardness of the resulting cured film can be made good.

[0101] The mass ratio (C / D) of the resin (C) to the polymerizable compound (D) in the curable composition is preferably 1 or more, more preferably 1.5 or more, still more preferably 2 or more, and preferably 8 or less, more preferably 6 or less, still more preferably 5 or less. When the mass ratio (C / D) of the resin (C) to the polymerizable compound (D) satisfies the above range, it is preferable that the photopolymerizable compound (D) contains one or more of the photopolymerizable compounds (Dα1), and it is more preferable that the photopolymerizable compound (D) contains one or more of the photopolymerizable compounds (Dα1) and one or more of the photopolymerizable compounds (Dβ1).

[0102] <Polymerization initiator (E)> The polymerization initiator (E) is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate the polymerization of the polymerizable compound (D). The curable composition can contain one or more polymerization initiators (E).

[0103] Examples of the polymerization initiator (E) include compounds represented by the formula (EA). Since the curable composition can be cured at a low temperature and the hardness of the resulting cured film can be made good when the polymerization initiator (E) contains a compound represented by the formula (EA), it is preferable that the polymerization initiator (E) contains a compound represented by the following formula (EA).

[0104] [Chemical formula] [In the formula, R ea1 represents a branched hydrocarbon group having 3 to 20 carbon atoms which may have a substituent. Rea2 ~R ea5 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. n represents any integer from 0 to 4. -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -OCO-.

[0105] R ea1 Examples of the branched hydrocarbon group having 3 to 20 carbon atoms represented by R include a branched saturated hydrocarbon group having 3 to 20 carbon atoms, a branched unsaturated hydrocarbon group having 3 to 20 carbon atoms, and the like.

[0106] R ea1Examples of the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by include 1-methylethyl group (isopropyl group), 1-methylpropyl group (sec-butyl group), 2-methylpropyl group (isobutyl group), 1,1-dimethylethyl group (tert-butyl group), 1,1-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1,1-dimethylpentyl group, 2,2-dimethylpentyl group, 3,3-dimethylpentyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentyl group, 2,3-dimethylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 1,1-dimethylhexyl group, 2,2-dimethylhexyl group, 3,3-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 2,3-dimethylhexyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group, 1,1-dimethylheptyl group, 2,2-dimethylheptyl group, 3,3-dimethylheptyl group, 1,2-dimethylheptyl group, 1,3-dimethylheptyl group, 2,3-dimethylheptyl group, 1-ethylheptyl group, 2-ethylheptyl group, 3-ethylheptyl group, 1-methyloctyl group, 2-methyloctyl group, 3-methyloctyl group, 4-methyloctyl group, 1,1-dimethyloctyl group, 2,2-dimethyloctyl group, 3,3-dimethyloctyl group, 1,2-dimethyloctyl group, 1,3-dimethyloctyl group, 2,Branched alkyl groups such as 3-dimethyloctyl group, 1-ethyloctyl group, 2-ethyloctyl group, 3-ethyloctyl group, 1-methylnonyl group, 2-methylnonyl group, 3-methylnonyl group, 4-methylnonyl group, dimethylnonyl group, ethylnonyl group, methyldecyl group, dimethyldecyl group, ethyldecyl group, methylundecyl group, dimethylundecyl group, ethylundecyl group, methyldodecyl group, etc.; are exemplified. R ea1 The branched alkyl group represented by may be any of a primary branched alkyl group, a secondary branched alkyl group, or a tertiary branched alkyl group. R ea1 The number of carbon atoms of the branched saturated hydrocarbon group represented by is preferably 4 or more, more preferably 5 or more, preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.

[0107] R ea1 Examples of the branched unsaturated hydrocarbon group represented by include those in which at least one carbon-carbon single bond contained in the branched saturated hydrocarbon group represented by the aforementioned R ea1 is replaced by a carbon-carbon double bond or a carbon-carbon triple bond, and the like. R ea1 Examples of the branched unsaturated hydrocarbon group represented by include alkenyl groups such as isopropenyl group, isobutenyl group, isopentenyl group, isohexenyl group, isoheptenyl group, isooctenyl group, isononyl group, isodecenyl group; alkynyl groups such as isopropynyl group, isobutinyl group, isopentynyl group, isohexynyl group, isoheptynyl group, isooctynyl group, isononynyl group, isodecynyl group; and the like. R ea1 The number of carbon atoms of the branched unsaturated hydrocarbon group represented by is preferably 4 or more, more preferably 5 or more, preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.

[0108] R ea2 R ea3 R ea4 and R ea5Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by include saturated hydrocarbon groups having 1 to 20 carbon atoms, unsaturated hydrocarbon groups having 2 to 20 carbon atoms, aromatic hydrocarbon groups having 6 to 20 carbon atoms, and the like. R ea2 , R ea3 , R ea4 and R ea5 The hydrocarbon groups represented by may be the same or different from each other.

[0109] Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group, and icosyl group; branched-chain alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and tricyclodecyl group. The number of carbon atoms of the saturated hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, still more preferably 1 to 10, and even more preferably 1 to 8.

[0110] Examples of the unsaturated hydrocarbon group having 2 to 20 carbon atoms include alkenyl groups such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, hexadecenyl group, octadecenyl group, and icosenyl group; alkynyl groups such as ethynyl group, propynyl group, hexynyl group, decynyl group, and icosenyl group; cycloalkenyl groups such as cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group; and the like. The number of carbon atoms of the unsaturated hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and still more preferably 2 to 10.

[0111] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, a benzyl group, a phenylethyl group, a phenylbutyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, and further preferably 6 to 12.

[0112] R ea1 , R ea2 , R ea3 , R ea4 and R ea5 Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include a halogen atom, a cyano group, and a nitro group. The halogen atom is preferably a fluorine atom, a bromine atom, a chlorine atom, or an iodine atom.

[0113] The -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -OCO-, provided that adjacent -CH2- are not simultaneously replaced by the same type of group, and the terminal -CH2- is not replaced.

[0114] n represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, further preferably an integer of 0 or 1, and even more preferably 0.

[0115] *-OCO-R ea4 The bonding position of the group (* represents a bond to the phenyl group) is the *-OCO-R ea4 The group may be bonded to any of the 2-, 3- or 4-positions of the phenyl group, but is preferably bonded to the 3- or 4-position, more preferably to the 4-position.

[0116] R ea1 The branched hydrocarbon group having 3 to 20 carbon atoms represented by the formula: A branched saturated hydrocarbon group having 3 to 20 carbon atoms is preferred. A branched alkyl group having 3 to 20 carbon atoms is more preferable. A branched alkyl group having 3 to 10 carbon atoms is more preferable. At least one selected from the group consisting of 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 1-ethylheptyl group, 2-ethylheptyl group and 3-ethylheptyl group is preferable.

[0117] R ea2 , R ea3 , R ea4 and R ea5 The hydrocarbon group having 1 to 20 carbon atoms represented by a saturated hydrocarbon group having 1 to 20 carbon atoms or an unsaturated hydrocarbon group having 2 to 20 carbon atoms is preferable, a saturated hydrocarbon group having 1 to 20 carbon atoms is more preferable, a linear saturated hydrocarbon group having 1 to 10 carbon atoms is even more preferable, a linear alkyl group having 1 to 8 carbon atoms is even more preferable. R ea2 is preferably a linear alkyl group having 1 to 8 carbon atoms, and more preferably a linear alkyl group having 1 to 6 carbon atoms. R ea3 is preferably a linear alkyl group having 1 to 8 carbon atoms, and more preferably a linear alkyl group having 1 to 3 carbon atoms. R ea4 is preferably a linear alkyl group having 1 to 8 carbon atoms, and more preferably a linear alkyl group having 1 to 3 carbon atoms. R ea5 is preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and more preferably a linear or branched alkyl group having 1 to 6 carbon atoms.

[0118] Further, as the polymerization initiator (E), a compound represented by the formula (EB) can be mentioned.

[0119] [In the formula, [wherein, Reb1 represents a branched hydrocarbon group having 3 to 20 carbon atoms which may have a substituent. R eb2 ~R eb4 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. m represents any integer from 0 to 4. -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -OCO-.

[0120] R eb1 Examples of the branched hydrocarbon group having 3 to 20 carbon atoms represented by R include a branched saturated hydrocarbon group having 3 to 20 carbon atoms, a branched unsaturated hydrocarbon group having 3 to 20 carbon atoms, and the like.

[0121] R eb1 Examples of the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by R are the same as those exemplified above for the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by R. ea1 Examples of the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by R can be the same as those exemplified above. R eb1 The branched-chain alkyl group represented by R may be any of a primary branched-chain alkyl group, a secondary branched-chain alkyl group, or a tertiary branched-chain alkyl group. R eb1 The number of carbon atoms of the branched saturated hydrocarbon group represented by R may be 4 or more, or 5 or more, and may also be 16 or less, 12 or less, or 10 or less.

[0122] R eb1 Examples of the branched unsaturated hydrocarbon group represented by R include a group in which at least one carbon-carbon single bond contained in the branched saturated hydrocarbon group represented by the aforementioned R is replaced by a carbon-carbon double bond or a carbon-carbon triple bond. eb1 Examples thereof include a group in which at least one carbon-carbon single bond contained in the branched saturated hydrocarbon group represented by the aforementioned R is replaced by a carbon-carbon double bond or a carbon-carbon triple bond. R eb1Examples of the branched unsaturated hydrocarbon group represented by the formula (I) include alkenyl groups such as an isopropenyl group, an isobutenyl group, an isopentenyl group, an isohexenyl group, an isoheptenyl group, an isooctenyl group, an isononyl group, and an isodecenyl group; and alkynyl groups such as an isopropynyl group, an isobutynyl group, an isopentynyl group, an isohexynyl group, an isoheptynyl group, an isooctynyl group, an isononynyl group, and an isodecynyl group. R eb1 The number of carbon atoms in the branched unsaturated hydrocarbon group represented by the formula (I) may be 4 or more, or 5 or more, and may be 16 or less, 12 or less, or 10 or less.

[0123] R eb2 , R eb3 and R eb4 Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include a saturated hydrocarbon group having 1 to 20 carbon atoms, an unsaturated hydrocarbon group having 2 to 20 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms. eb2 , R eb3 and R eb4 The hydrocarbon groups represented by the following formula may be the same or different.

[0124] Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups. The number of carbon atoms in the saturated hydrocarbon group may be 1 to 18, 1 to 15, 1 to 10, or 1 to 8.

[0125] Examples of the unsaturated hydrocarbon group having 2 to 20 carbon atoms include alkenyl groups such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, hexadecenyl group, octadecenyl group, and icosenyl group; alkynyl groups such as ethynyl group, propynyl group, hexynyl group, decynyl group, and icosenyl group; cycloalkenyl groups such as cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group; etc. The number of carbon atoms in the unsaturated hydrocarbon group may be 2 to 18, 2 to 15, or 2 to 10.

[0126] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, a benzyl group, a phenylethyl group, a phenylbutyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group may be 6 to 18, 6 to 15, or 6 to 12.

[0127] R eb1 , R eb2 , R eb3 and R eb4 Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include a halogen atom, a cyano group, and a nitro group. Examples of the halogen atom include a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom, and may be a fluorine atom.

[0128] The -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -OCO-, in particular may be replaced by -O-, provided that adjacent -CH2- are not simultaneously replaced by the same group, and the terminal -CH2- is not replaced.

[0129] m represents an integer of 0 to 4, and may be an integer of 1 to 3, an integer of 2 to 3, or 3.

[0130] If m is 1 or more, then *-R eb4 At least one of the 2-, 4- and 6-positions of the phenyl group to which is bonded, *-R eb4(* represents a bond to a phenyl group), and *-R is bonded. eb4 *-R is bonded to at least two of the 2-position, 4-position, and 6-position of the phenyl group to which it is bonded. eb4 or *-R is bonded. eb4 *-R is bonded to all of the 2-position, 4-position, and 6-position of the phenyl group to which it is bonded. eb4 Examples include the above.

[0131] R eb1 The branched hydrocarbon group having 3 to 20 carbon atoms represented by R is a branched saturated hydrocarbon group having 3 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, or a branched-chain alkyl group having 3 to 10 carbon atoms, etc., may be used. Examples include one or more selected from the group consisting of 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 1-ethylheptyl group, 2-ethylheptyl group, and 3-ethylheptyl group.

[0132] R eb2 The hydrocarbon group having 1 to 20 carbon atoms represented by R may be an aromatic hydrocarbon group having 6 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 17 carbon atoms, an aromatic hydrocarbon group having 7 to 15 carbon atoms, or an aromatic hydrocarbon group having 8 to 13 carbon atoms. In any of these preferred embodiments, it may have 1 to 8 (especially 1 to 5) fluorine atoms as substituents and may have a structure in which 1 to 2 -CH2- are replaced by -O-.

[0133] R eb2 Preferred embodiments of the aromatic hydrocarbon group having 8 to 13 carbon atoms for R include the following (eb2-1) to (eb2-6), etc.

[0134]

Chemical formula

[0135] R eb3 and R eb4 The hydrocarbon group having 1 to 20 carbon atoms represented by each is independently It may be a saturated hydrocarbon group having 1 to 20 carbon atoms or an unsaturated hydrocarbon group having 2 to 20 carbon atoms, a saturated hydrocarbon group having 1 to 20 carbon atoms, a linear saturated hydrocarbon group having 1 to 10 carbon atoms, a linear alkyl group having 1 to 8 carbon atoms, or a linear alkyl group having 1 to 3 carbon atoms.

[0136] In addition, when -CH2- contained in the hydrocarbon group in formula (EB) is replaced by -O-, -S-, -CO- or -OCO-, the carbon number of this replaced part shall be counted as the carbon number of -CH2- before replacement.

[0137] Examples of the polymerization initiator (E) other than the compound represented by formula (EA) include photopolymerization initiators such as oxime compounds (excluding the compounds represented by formula (EA) and formula (EB)), alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine compounds, and thermal polymerization initiators such as azo compounds and organic peroxides.

[0138] An example of the oxime compound (excluding the compounds represented by formula (EA) and formula (EB)) is an oxime compound having a first molecular structure represented by the following formula (1). Hereinafter, this oxime compound is also referred to as "oxime compound (1)".

[0139]

Chemical formula

[0140] Including the oxime compound (1) as the polymerization initiator (E) can be advantageous from the viewpoint of improving the intensity of the emitted light. One of the reasons for such an effect is that due to the specific molecular structure of the oxime compound (1), the absorption wavelength of the oxime compound (1) changes significantly before and after the cleavage (decomposition) of the oxime compound (1) required for the oxime compound (1) to initiate photopolymerization. Therefore, it is presumed that the oxime compound (1) has a high photo radical polymerization initiation ability.

[0141] In formula (1), R 1 represents R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN.

[0142] R 11 , R 12 and R 13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0143] R 11 , R 12 or R 13 The hydrogen atom of the group represented by is OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 may be substituted.

[0144] R 21 , R 22and R 23 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0145] R 21 、R 22 or R 23 The hydrogen atom of the group represented by may be substituted with a CN, a halogen atom, a hydroxy group, or a carboxy group.

[0146] R 11 、R 12 、R 13 、R 21 、R 22 or R 23 When the group represented by has an alkylene moiety, the alkylene moiety may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.

[0147] R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0148] R 11 、R 12 、R 13 、R 21 、R 22 or R 23 When the group represented by has an alkyl moiety, the alkyl moiety may be branched, cyclic, and R 12 and R 13 and R 22 and R 23 may together form a ring.

[0149] * represents a bond with a second molecular structure which is a molecular structure other than the first molecular structure that the oxime compound (1) has.

[0150] R in formula (1) 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 Examples of the alkyl group having 1 to 20 carbon atoms represented by R include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, tert-pentyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, tert-octyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, eicosyl group, cyclopentyl group, cyclohexyl group, cyclohexylmethyl group, cyclohexylethyl group and the like.

[0151] R in formula (1) 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 Examples of the aryl group having 6 to 30 carbon atoms represented by R include phenyl group, tolyl group, xylyl group, ethylphenyl group, naphthyl group, anthryl group, phenanthryl group, phenyl group substituted with one or more of the above alkyl groups, biphenylyl group, naphthyl group, anthryl group and the like.

[0152] R in formula (1) 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 Examples of the aralkyl group having 7 to 30 carbon atoms represented by R include benzyl group, α-methylbenzyl group, α,α-dimethylbenzyl group, phenylethyl group and the like.

[0153] R in formula (1) 11 , R 12 , R13 and R 21 and R 22 and R 23 and R 24 Examples of the heterocyclic group having 2 to 20 carbon atoms represented by include a pyridyl group, a pyrimidyl group, a furyl group, a thienyl group, a tetrahydrofuryl group, a dioxolanyl group, a benzoxazol-2-yl group, a tetrahydropyranyl group, a pyrrolidyl group, an imidazolidyl group, a pyrazolidyl group, a thiazolidyl group, an isothiazolidyl group, an oxazolidyl group, an isoxazolidyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, etc. Preferably, it is a 5- to 7-membered heterocycle.

[0154] R in formula (1) 12 and R 13 and R 22 and R 23 each may form a ring together means that R 12 and R 13 and R 22 and R 23 each may form a ring together with the connecting nitrogen atom, carbon atom or oxygen atom, respectively.

[0155] R in formula (1) 12 and R 13 and R 22 and R 23 Examples of the ring that can be formed together include a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a benzene ring, a piperidine ring, a morpholine ring, a lactone ring, a lactam ring, etc. Preferably, it is a 5- to 7-membered ring.

[0156] R in formula (1) 11 R 12 R 13 R 21 R 22 and R 23 Examples of the halogen atom that may be a substituent include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0157] R in formula (1) 1 is preferably R 11and more preferably an alkyl group having 1 to 20 carbon atoms, still more preferably an alkyl group having 1 to 10 carbon atoms, and even still more preferably an alkyl group having 1 to 6 carbon atoms.

[0158] An example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by the following formula (2). The second molecular structure means another molecular structure part other than the above first molecular structure that the oxime compound (1) has.

[0159] In formula (2), the bond represented by "*" is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (2), the benzene ring having "-*" in formula (2) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0160] [Chemical formula]

[0161] In formula (2), R 2 and R 3 each independently represent R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 , COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 , CN or a halogen atom.

[0162] When there are a plurality of R 2 , they may be the same or different.

[0163] When there are a plurality of R 3 , they may be the same or different.

[0164] R 11 、R 12 and R 13 represents the same meaning as described above.

[0165] s and t each independently represent an integer from 0 to 4.

[0166] L represents a sulfur atom, CR 31 R 32 , CO or NR 33 represents.

[0167] R 31 、R 32 and R 33 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms.

[0168] R 31 、R 32 or R 33 If the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 31 、R 32 and R 33 each independently may combine with either adjacent benzene ring to form a ring.

[0169] R 4 represents a hydroxy group, a carboxy group or the following formula (2-1)

[0170]

Chemical formula

[0171] (In formula (2-1), L 1 represents -O-, -S-, -NR 22 -, -NR 22 CO-, -SO2-, -CS-, -OCO- or -COO-.

[0172] R 22 represents the same meaning as described above.

[0173] L 2 represents a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms, a group obtained by removing v hydrogen atoms from an aralkyl group having 7 to 30 carbon atoms, or a group obtained by removing v hydrogen atoms from a heterocyclic group having 2 to 20 carbon atoms.

[0174] L 2 When the group represented by has an alkylene moiety, the alkylene moiety may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 22 -, -NR 22 COO-, -OCONR 22 -, -SCO-, -COS-, -OCS- or -CSO-, and the alkylene moiety may be branched or cyclic.

[0175] R 4a is OR 41 、SR 41 、CONR 42 R 43 、NR 42 COR 43 、OCOR 41 、COOR 41 、SCOR 41 、OCSR 41 、COSR 41 、CSOR 41 、CN or a halogen atom.

[0176] R 4a When there are a plurality of them, they may be the same or different.

[0177] R 41 、R 42 and R 43 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms, and when the groups represented by R 41 、R 42 and R 43 have an alkyl moiety, the alkyl moiety may be branched or cyclic, and R42 and R 43 may combine together to form a ring.

[0178] v represents an integer from 1 to 3.) represents a group represented by

[0179] * represents a bond with the first molecular structure possessed by the oxime compound (1).

[0180] R in formula (2) 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 24 , R 31 , R 32 and R 33 , and the examples of the alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, and aralkyl group having 7 to 30 carbon atoms represented by R in the above formula (2-1) 22 , R 41 , R 42 and R 43 are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1).

[0181] R in formula (2) 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 24 , and the examples of the heterocyclic group having 2 to 20 carbon atoms represented by R in the above formula (2-1) 22 are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1).

[0182] R in formula (2) 31 R 32 and R 33 each independently may combine with either adjacent benzene ring to form a ring, which means that R 31 R 32 and R 33 each independently may combine with either adjacent benzene ring to form a ring together with the connecting nitrogen atom.

[0183] R in formula (2) 31 R 32 and R 33 Examples of rings that can be formed by combining with either adjacent benzene ring are the same as the examples of rings that can be formed by combining R 12 with R 13 and R 2 with R 23 in formula (1).

[0184] L in the above formula (2-1) 2 represents a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0185] Examples of the group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms include, for example, when v = 1, methylene group, ethylene group, propylene group, methylethylene group, butylene group, 1-methylpropylene group, 2-methylpropylene group, 1,2-dimethylpropylene group, 1,3-dimethylpropylene group, 1-methylbutylene group, 2-methylbutylene group, 3-methylbutylene group, 4-methylbutylene group, 2,4-dimethylbutylene group, 1,3-dimethylbutylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, dodecylene group, tridecylene group, tetradecylene group, pentadecylene group, ethane-1,1-diyl group, propane-2,2-diyl group, and other alkylene groups.

[0186] Examples of the group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms include, when v = 1, an arylene group such as 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 2,6-naphthylene group, 1,4-naphthylene group, 2,5-dimethyl-1,4-phenylene group, diphenylmethane-4,4'-diyl group, 2,2-diphenylpropane-4,4'-diyl group, diphenylsulfide-4,4'-diyl group, diphenylsulfone-4,4'-diyl group, etc.

[0187] Examples of the group obtained by removing v hydrogen atoms from an aralkyl group having 7 to 30 carbon atoms include, when v = 1, the group represented by the following formula (a) and the group represented by the following formula (b), etc.

[0188] [Chemical formula]

[0189] [In formulas (a) and (b), L 3 and L 5 represent an alkylene group having 1 to 10 carbon atoms, and L 4 and L 6 represent a single bond or an alkylene group having 1 to 10 carbon atoms.] Examples of the alkylene group having 1 to 10 carbon atoms include, for example, methylene group, ethylene group, propylene group, methylethylene group, butylene group, 1-methylpropylene group, 2-methylpropylene group, 1,2-dimethylpropylene group, 1,3-dimethylpropylene group, 1-methylbutylene group, 2-methylbutylene group, 3-methylbutylene group, 4-methylbutylene group, 2,4-dimethylbutylene group, 1,3-dimethylbutylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, etc.

[0190] Examples of the group obtained by removing v hydrogen atoms from a complex ring group having 2 to 20 carbon atoms include, for example, when v is 1, divalent complex ring groups such as 2,5-pyridinediyl group, 2,6-pyridinediyl group, 2,5-pyrimidinediyl group, 2,5-thiophenediyl group, 3,4-tetrahydrofurandiyl group, 2,5-tetrahydrofurandiyl group, 2,5-furandiyl group, 3,4-thiazolediyl group, 2,5-benzofurandiyl group, 2,5-benzothiophenediyl group, N-methylindole-2,5-diyl group, 2,5-benzothiazolediyl group, 2,5-benzoxazolediyl group, etc.

[0191] R in formula (2) 2 and R 3 , and also R in the above formula (2-1) 4a Examples of the halogen atom represented by include fluorine atom, chlorine atom, bromine atom and iodine atom.

[0192] From the viewpoints of solubility in the solvent (J) and / or developability of the curable composition, a preferable example of the structure represented by formula (2) is the structure represented by the following formula (2a).

[0193]

Chemical formula

[0194] [In formula (2a), L’ represents a sulfur atom or NR 50 , R 50 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and R 2 , R 3 , R 4 , s and t represent the same meanings as described above.] From the same viewpoints as above, another preferable example of the structure represented by formula (2) is the structure represented by the following formula (2b).

[0195]

Chemical formula

[0196] [In formula (2b), R 44 represents a hydroxy group, a carboxy group, or the following formula (2-2)

[0197] [Chemical formula]

[0198] (In formula (2-2), L 11 represents *-O- or *-OCO-, where * represents the bond with L 12 and L 12 represents an alkylene group having 1 to 20 carbon atoms, and the alkylene group may be interrupted by 1 to 3 -O-'s. R 44a represents OR 55 or COOR 55 and R 55 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) represents a group represented by.)] R 44 is preferably a group represented by formula (2-2). In this case, it is advantageous in terms of the solubility of the oxime compound (1) in the solvent (J) and the developability of the curable composition.

[0199] The carbon number of the alkylene group represented by L 12 is preferably 1 to 10, more preferably 1 to 4.

[0200] R 44a is preferably a hydroxy group or a carboxy group, more preferably a hydroxy group.

[0201] The method for producing the oxime compound (1) having the second molecular structure represented by formula (2) is not particularly limited. For example, it can be produced by the method described in JP-A-2011-132215.

[0202] Another example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by the following formula (3).

[0203] In formula (3), the bond represented by "*" is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is the structure represented by formula (3), the benzene ring having "-*" in formula (3) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0204]

Chemical formula

[0205] In formula (3), R 5 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0206] R 5 When the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic.

[0207] R 5 The hydrogen atom of the group represented by is R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR 21 and may be substituted.

[0208] R 21 、R 22 and R 23 have the same meaning as described above.

[0209] R 21 、R 22 or R 23 The hydrogen atom of the group represented by may be substituted with a CN, a halogen atom, a hydroxy group or a carboxy group.

[0210] R 21 、R 22 and R 23 When the group represented by has an alkylene moiety, the alkylene moiety may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.

[0211] R 24 has the same meaning as described above.

[0212] R 21 、R 22 and R 23 When the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 22 and R 23 may combine together to form a ring.

[0213] R 6 、R 7 、R 8 and R 9 each independently represents R 61 、OR 61 、SR 61 、COR 62 、CONR 63 R 64 、NR 65 COR 61 、OCOR 61 、COOR 62, SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , represents a hydroxyl group, nitro group, CN or halogen atom.

[0214] R 61 , R 62 , R 63 , R 64 and R 65 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.

[0215] R 61 , R 62 , R 63 , R 64 or R 65 The hydrogen atom of the group represented by is OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , CN, halogen atom, or COOR 21 may be substituted.

[0216] R 6 and R 7 , R 7 and R 8 and R 8 and R 9 may together form a ring.

[0217] * represents a bond with the first molecular structure of the oxime compound (1).

[0218] R in formula (3) 5, R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 Examples of the alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, and heterocyclic group having 2 to 20 carbon atoms represented by are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 The same as the examples for.

[0219] R in formula (3) 22 and R 23 may combine to form a ring, which means that R 22 and R 23 may combine to form a ring together with the connecting nitrogen atom, carbon atom or oxygen atom.

[0220] Examples of the ring that R in formula (3) 22 and R 23 can form together are the same as the examples of the rings that R in formula (1) 12 and R 13 and R 22 and R 23 can form together.

[0221] R in formula (3) 6 , R 7 , R 8 and R 9 Examples of the halogen atom represented by, R 5 , R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 Examples of the halogen atom that may substitute the hydrogen atom of include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0222] From the viewpoint of solubility in the solvent (J) and / or developability of the curable composition, in one preferred form, R 5 is a group represented by the following formula (3-1).

[0223] [Chemical formula]

[0224] [In formula (3-1), Z represents a group obtained by removing one hydrogen atom from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing one hydrogen atom from an aryl group having 6 to 30 carbon atoms, a group obtained by removing one hydrogen atom from an aralkyl group having 7 to 30 carbon atoms, or a group obtained by removing one hydrogen atom from a heterocyclic group having 2 to 20 carbon atoms. When the group represented by Z has an alkylene moiety, the alkylene moiety may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR -, -NR 24 -, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-, and the alkylene moiety may be branched or cyclic. R R 21 , R 22 and R 24 represent the same meaning as described above.] From the same viewpoint as above, Z in formula (3-1) is preferably a methylene group, an ethylene group or a phenylene group.

[0225] R 21 and R 22 in formula (3-1) are preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms from the same viewpoint as above, and more preferably a methyl group, an ethyl group or a phenyl group.

[0226] From the same viewpoint as above, in another preferred form, R 7 is a nitro group.

[0227] The method for producing the oxime compound (1) having the second molecular structure represented by the formula (3) is not particularly limited. For example, it can be produced by the methods described in JP-A-2000-80068 and JP-A-2011-178776.

[0228] Still another example of the second molecular structure linked to the first molecular structure represented by the formula (1) is a structure represented by the following formula (4).

[0229] In the formula (4), the bond represented by "*" is directly bonded to the bond represented by "*" in the formula (1). That is, when the second molecular structure is a structure represented by the formula (4), the benzene ring having "-*" in the formula (4) and the carbonyl group having "-*" in the formula (1) are directly bonded.

[0230] [Chemical formula]

[0231] In the formula (4), R 71 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0232] R 71 When the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic.

[0233] R 71 The hydrogen atom of the group represented by is R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , NR 22 COR 21 , OCOR 21, COOR 21 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR 21 may be substituted therewith.

[0234] R 21 , R 22 and R 23 represent the same meaning as described above.

[0235] R 21 , R 22 or R 23 The hydrogen atom of the group represented by may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.

[0236] R 21 , R 22 and R 23 When the group represented by has an alkylene moiety, the alkylene moiety may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.

[0237] R 24 represents the same meaning as described above.

[0238] R 21 , R 22 and R 23 When the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 22 and R 23 may combine together to form a ring.

[0239] R72 、R 73 and three Rs 74 are each independently R 61 、OR 61 、SR 61 、COR 62 、CONR 63 R 64 、NR 65 COR 61 、OCOR 61 、COOR 62 、SCOR 61 、OCSR 61 、COSR 62 、CSOR 61 、represent a hydroxyl group, a nitro group, CN or a halogen atom.

[0240] R 61 、R 62 、R 63 、R 64 and R 65 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.

[0241] R 61 、R 62 、R 63 、R 64 or R 65 The hydrogen atom of the group represented by is OR 21 、COR 21 、SR 21 、NR 22 R 23 、CONR 22 R 23 、-NR 22 -OR 23 、-N(COR 22 )-OCOR 23 、-C(=N-OR 21 )-R 22 、-C(=N-OCOR 21 )-R 22 、CN, a halogen atom, or COOR 21 and may be substituted.

[0242] R 72 and R73 and two Rs 74 may combine together to form a ring.

[0243] * represents a bond with the first molecular structure of the oxime compound (1).

[0244] R in formula (4) 71 R 21 R 22 R 23 R 24 R 61 R 62 R 63 R 64 and R 65 Examples of the alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, and heterocyclic group having 2 to 20 carbon atoms represented by are the same as the examples for R 11 R 12 R 13 R 21 R 22 R 23 and R 24 in formula (1).

[0245] R in formula (4) 22 and R 23 may combine together to form a ring means that R 22 and R 23 may combine together with the connecting nitrogen atom, carbon atom or oxygen atom to form a ring.

[0246] R in formula (4) 22 and R 23 Examples of the ring that can be formed by combining together are the same as the examples of the ring that can be formed by combining R 12 and R 13 and R 22 and R 23 in formula (1).

[0247] R in formula (4) 72 R 73 and R 74 represent a halogen atom, R 71 R 21 R22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 Examples of the halogen atom that may replace the hydrogen atom of R, R, R, R, R, and R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0248] The method for producing the oxime compound (1) having the second molecular structure represented by the formula (4) is not particularly limited. For example, it can be produced by the methods described in International Publication No. 2017 / 051680 and International Publication No. 2020 / 004601.

[0249] Another example of the second molecular structure linked to the first molecular structure represented by the formula (1) is the structure represented by the following formula (5).

[0250] In the formula (5), the bond represented by "*" is directly bonded to the bond represented by "*" in the formula (1). That is, when the second molecular structure is the structure represented by the formula (5), the pyrrole ring having "-*" in the formula (5) and the carbonyl group having "-*" in the formula (1) are directly bonded.

[0251]

Chemical formula

[0252] In the formula (5), R 81 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0253] R 81 When the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic.

[0254] R 81 The hydrogen atom of the group represented by is R 21 , OR 21 , COR 21, SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 , -OR 23 , -N(COR 22 )-OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR 21 may be substituted.

[0255] R 21 , R 22 and R 23 have the same meaning as described above.

[0256] R 21 , R 22 or R 23 the hydrogen atom of the group represented by may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.

[0257] R 21 , R 22 and R 23 when the group represented by has an alkylene moiety, the alkylene moiety may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.

[0258] R 24 has the same meaning as described above.

[0259] R 21 、R 22 and R 23 when the group represented by has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 22 and R 23 may combine together to form a ring.

[0260] R 82 、R 83 、R 84 、R 85 and R 86 each independently represents R 61 、OR 61 、SR 61 、COR 62 、CONR 63 R 64 、NR 65 COR 61 、OCOR 61 、COOR 62 、SCOR 61 、OCSR 61 、COSR 62 、CSOR 61 、a hydroxyl group, a nitro group, CN or a halogen atom.

[0261] R 61 、R 62 、R 63 、R 64 and R 65 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.

[0262] R 61 、R 62 、R 63 、R 64 or R 65 the hydrogen atom of the group represented by is OR 21 、COR 21 、SR 21 、NR 22 R 23 、CONR 22 R 23 、-NR 22 -OR23 , -N(COR 22 )-OCOR 23 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 may be substituted.

[0263] R 83 and R 84 , R 84 and R 85 and R 85 and R 86 may together form a ring.

[0264] * represents a bond with the first molecular structure of the oxime compound (1).

[0265] R in formula (5) 81 , R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 Examples of the alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, and heterocyclic group having 2 to 20 carbon atoms represented by are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1).

[0266] R in formula (5) 22 and R 23 may together form a ring means that R 22 and R 23 may together form a ring with the connecting nitrogen atom, carbon atom or oxygen atom.

[0267] R in formula (5)22 and R 23 Examples of rings that can be formed by combining R 12 and R 13 and R 22 and R 23 are the same as the examples of rings that can be formed by combining them.

[0268] R in formula (5) 82 , R 83 , R 84 , R 85 and R 86 represents a halogen atom, R 81 , R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 Examples of halogen atoms that may replace the hydrogen atoms of are fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0269] The method for producing the oxime compound (1) having the second molecular structure represented by formula (5) is not particularly limited, but for example, it can be produced by the methods described in International Publication No. 2017 / 051680 and International Publication No. 2020 / 004601.

[0270] Yet another example of the second molecular structure linked to the first molecular structure represented by formula (1) is the structure represented by the following formula (6).

[0271] In formula (6), the bond represented by "*" is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is the structure represented by formula (6), the benzene ring having "-*" in formula (6) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0272]

Chemical formula

[0273] In formula (6), the four Rs 91 , R 92 , R 93 , R 94 , R 95 , R 96 and R 97 are each independently R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN, or a halogen atom.

[0274] R 61 , R 62 , R 63 , R 64 and R 65 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0275] R 61 , R 62 , R 63 , R 64 or R 65 The hydrogen atom of the group represented by is OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21may be replaced.

[0276] R 21 、R 22 and R 23 represent the same meaning as described above.

[0277] R 92 and R 93 、R 94 and R 95 、R 95 and R 96 and R 96 and R 97 may together form a ring.

[0278] * represents a bond with the first molecular structure of the oxime compound (1).

[0279] R in formula (6) 21 、R 22 、R 23 、R 61 、R 62 、R 63 、R 64 and R 65 Examples of the alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, and heterocyclic group having 2 to 20 carbon atoms represented by are the same as the examples for R in formula (1) 11 、R 12 、R 13 、R 21 、R 22 and R 23 is the same.

[0280] R in formula (6) 22 and R 23 may together form a ring means that R 22 and R 23 may together form a ring with the connecting nitrogen atom, carbon atom or oxygen atom.

[0281] R in formula (6) 22 and R 23 Examples of the ring that can be formed together are the same as those of R in formula (1) 12 and R 13and R 22 and R 23 is the same as the example of the ring that can be formed by combining them.

[0282] R in formula (6) 91 、R 92 、R 93 、R 94 、R 95 、R 96 and R 97 and the halogen atoms represented by R 21 、R 22 、R 23 、R 61 、R 62 、R 63 、R 64 and R 65 Examples of the halogen atoms that may substitute the hydrogen atoms of R, R, R, R, R, R, R, R, R, R, R, R, R, R, and R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0283] The method for producing the oxime compound (1) having the second molecular structure represented by formula (6) is not particularly limited, and for example, it can be produced by the methods described in International Publication No. 2017 / 051680 and International Publication No. 2020 / 004601.

[0284] Examples of the oxime compound that is other than the compound represented by formula (EA) and other than the oxime compound (1) include an oxime compound having a partial structure represented by the following formula (d1). * represents a bond.

[0285]

Chemical formula

[0286] Examples of the oxime compound having the partial structure represented by the formula (d1) include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine; compounds described in JP-A-2011-132215, WO2008 / 78678, WO2008 / 78686, WO2012 / 132558, etc. may be mentioned. Commercially available products such as Irgacure OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine), OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine) (manufactured by BASF), N-1919 (manufactured by ADEKA), etc. may also be used.

[0287] Among them, the oxime compound having the partial structure represented by the formula (d1) is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine or N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine.

[0288] The alkylphenone compound is a compound having a partial structure represented by the following formula (d2) or a partial structure represented by the following formula (d3). In these partial structures, the benzene ring may have a substituent. * represents a bond.

[0289]

Chemical formula

[0290] Examples of the compound having the structure represented by the formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, and the like. Commercially available products such as OMNIRAD (registered trademark) 369, 907, 379 (manufactured by IGM Resins) may also be used.

[0291] Examples of the compound having the structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzyl dimethyl ketal, and the like.

[0292] In terms of sensitivity, as the alkylphenone compound, a compound having the structure represented by the formula (d2) is preferred.

[0293] Examples of the biimidazole compound include, for example, a compound represented by the formula (d5).

[0294] [Chemical formula]

[0295] [In the formula (d5), R E ~R J each represents an aryl group having 6 to 10 carbon atoms which may have a substituent.] Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a toluyl group, a xylyl group, an ethylphenyl group, a naphthyl group, and the like, and a phenyl group is preferred.

[0296] Examples of the substituent include a halogen atom, an alkoxy group having 1 to 4 carbon atoms, and the like. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and a chlorine atom is preferred. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and the like, and a methoxy group is preferred.

[0297] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-06-75372 and JP-A-06-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboxyalkoxy groups (see, for example, JP-A-7-10913), and the like. Among them, compounds represented by the following formula or mixtures thereof are preferred.

[0298]

Chemical formula

[0299] Examples of the triazine compound include, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-dimethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, etc. Among them, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine is preferable.

[0300] Examples of the acylphosphine compound include, for example, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, (2,4,6-trimethylbenzoyl)diphenylphosphine oxide, etc.

[0301] Another example of the photopolymerization initiator includes, for example, benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, 4,4'-bis(diethylamino)benzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds, etc.

[0302] The content of the polymerization initiator (E) in the curable composition is preferably 0.1 part by mass or more and 300 parts by mass or less, more preferably 0.1 part by mass or more and 200 parts by mass or less, based on 100 parts by mass of the polymerizable compound (D). Further, the content of the polymerization initiator (E) in the curable composition is preferably 0.1 part by mass or more and 30 parts by mass or less, more preferably 0.5 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the resin (C) and the polymerizable compound (D). When the content of the polymerization initiator (E) is within the above range, the curable composition can be cured at a low temperature, and the hardness of the obtained cured film can be made good.

[0303] The content ratio of the polymerization initiator (E) in the curable composition is, for example, 0.01% by mass or more and 20% by mass or less, preferably 0.1% by mass or more and 15% by mass or less, more preferably 0.5% by mass or more and 10% by mass or less, still more preferably 1% by mass or more and 8% by mass or less, even more preferably 1.5% by mass or more and 5% by mass or less, based on the total amount of the solid content of the curable composition.

[0304] The polymerization initiator (E) preferably contains a compound represented by the formula (EA), and the content ratio of the compound represented by the formula (EA) in the polymerization initiator (E) is preferably 30% by mass or more and 100% by mass or less, more preferably 50% by mass or more and 100% by mass or less, still more preferably 70% by mass or more and 100% by mass or less, even more preferably 80% by mass or more and 100% by mass or less, particularly preferably 90% by mass or more and 100% by mass or less, most preferably 95% by mass or more and 100% by mass or less, and may be 100% by mass, based on the total amount of the polymerization initiator (E).

[0305] <Light stabilizer (F)> As the light stabilizer (F), in addition to including a known light stabilizer (Fa), any additive having an action of stabilizing the components against light may be used. The light stabilizer (F) of the present invention also includes an antioxidant (Fb) and an ultraviolet absorber (Fc) that absorbs light and renders it harmless. The curable composition may contain two or more light stabilizers (F).

[0306] <Light stabilizer (Fa)> Examples of the light stabilizer (Fa) include hindered amine-based light stabilizers, acrylate-based light stabilizers, nickel-based light stabilizers, and oxamide-based light stabilizers.

[0307] <Antioxidants (Fb)> The antioxidant (Fb) is not particularly limited as long as it is an antioxidant generally used industrially, and may be a phenol-based antioxidant, a phosphorus-based antioxidant, a phosphorus / phenol complex type antioxidant, a sulfur-based antioxidant, etc. The curable composition may contain two or more types of antioxidants (Fb).

[0308] The phosphorus / phenol complex type antioxidant is, for example, a compound having one or more phosphorus atoms and one or more phenol structures in the molecule. Among them, from the viewpoints of the developability and emitted light intensity of the curable composition, it is preferable that the antioxidant (Fb) contains a phosphorus / phenol complex type antioxidant.

[0309] Examples of phenolic antioxidants include Irganox (registered trademark) 1010 (Irganox 1010: pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), 1076 (Irganox 1076: octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF Corporation), 1330 (Irganox 1330: 3,3’,3’’,5,5’,5’’-hexa-tert-butyl-a,a’,a’’-(mesitylene-2,4,6-triyl)tri-p-cresol, manufactured by BASF Corporation), 3114 (Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), 3790 (Irganox 3790: 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), 1035 (Irganox 1035: thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), 1135 (Irganox 1135: 3,5-bis(1,1-dimethylethyl)-4-hydroxy-C7-C9 branched alkyl ester of benzenepropanoic acid, manufactured by BASF Corporation), 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Corporation), 3125 (Irganox 3125, manufactured by BASF Corporation), 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy-3’,5’-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF Corporation), Adeka Stab (registered trademark) AO-80 (Adeka Stab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5) Undecane (manufactured by ADEKA Co., Ltd.), Sumilizer (registered trademark) BHT, Sumilizer GA-80, and Sumilizer GS (all manufactured by Sumitomo Chemical Co., Ltd.), Cyanox (registered trademark) 1790 (manufactured by Cytec Co., Ltd.), and Vitamin E (manufactured by Eisai Co., Ltd.).

[0310] Examples of phosphorus-based antioxidants include Irgafos (registered trademark) 168 (Irgafos 168: tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF Co., Ltd.), Irgafos 12 (Irgafos 12: tris[2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl]oxy]ethyl]amine, manufactured by BASF Co., Ltd.), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Co., Ltd.), Adeka STAB (registered trademark) 329K, Adeka STAB PEP36, Adeka STAB PEP-8 (all manufactured by ADEKA Co., Ltd.), Sandstab Examples of such antibacterial agents include P-EPQ (manufactured by Clariant), Weston (registered trademark) 618, Weston 619G (all manufactured by GE), and Ultranox 626 (manufactured by GE).

[0311] Examples of phosphorus / phenol complex antioxidants include Sumilizer (registered trademark) GP (6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphosphepine) (manufactured by Sumitomo Chemical Co., Ltd.).

[0312] Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl, dimyristyl, and distearyl thiodipropionate, and β-alkyl mercaptopropionate compounds of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane.

[0313] <Ultraviolet absorber (Fc)> Examples of the ultraviolet absorber (Fc) include benzotriazole compounds such as 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole and 2-(2,4-dihydroxyphenyl)-2H-benzotriazole; benzophenone compounds such as 2-hydroxy-4-octyloxybenzophenone; benzoate compounds such as 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate; triazine compounds such as 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexyloxyphenol; and the like.

[0314] The content of the light stabilizer (F) in the curable composition (total amount in the case of multiple types) is, for example, 1 part by mass or more and 40 parts by mass or less with respect to 100 parts by mass of the resin (C). From the viewpoint of the emitted light intensity, it is preferably 2 parts by mass or more and 30 parts by mass or less, more preferably 3 parts by mass or more and 20 parts by mass or less.

[0315] When the curable composition contains the light stabilizer (F), the light stabilizer (F) is preferably an antioxidant (Fb) and / or an ultraviolet absorber (Fc).

[0316] <Leveling agent (H)> Examples of the leveling agent (H) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain. The leveling agent (H) preferably contains a silicone surfactant. The curable composition may contain two or more kinds of the leveling agent (H).

[0317] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan G.K.) etc. can be mentioned.

[0318] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Ltd.), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, F575, R30, RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc. can be mentioned.

[0319] Examples of silicone surfactants having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation) etc. can be mentioned.

[0320] When the curable composition contains a leveling agent (H), the content of the leveling agent (H) in the curable composition is, for example, 0.001% by mass or more and 1.0% by mass or less, preferably 0.005% by mass or more and 0.75% by mass or less, more preferably 0.01% by mass or more and 0.5% by mass or less, based on the total amount of the curable composition. When the content of the leveling agent (H) is within the above range, the flatness of the cured film can be made better.

[0321] <Solvent (J)> Solvent (J) dissolves the resin (C) and the polymerizable compound (D) and the polymerization initiator (E) used in the preferred embodiments. Examples of the solvent (J) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.

[0322] Examples of the ester solvent include methyl lactate, ethyl lactate, n-butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, isopropyl butyrate, ethyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate and γ-butyrolactone.

[0323] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

[0324] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate, and the like.

[0325] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0326] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0327] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0328] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0329] The solvent (J) preferably contains one or more selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, cyclohexyl acetate, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and aromatic hydrocarbon solvents.

[0330] The solvent (J) is preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, cyclohexyl acetate, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone or toluene, or a mixture of two or more thereof.

[0331] The solvent (J) is a component other than the solid content, and for example, the solvent contained in a solution of the resin (C) is also included in the solvent (J).

[0332] The content rate of the solvent (J) in the curable composition is the ratio of the total mass of all solvents contained in the curable composition to the total amount of the curable composition, and is, for example, 40% by mass or more and 95% by mass or less, preferably 50% by mass or more and 90% by mass or less with respect to the total amount of the curable composition. In other words, the solid content of the curable composition is, for example, 5% by mass or more and 60% by mass or less, preferably 10% by mass or more and 50% by mass or less. When the content rate of the solvent (J) is within the above range, the flatness of the curable composition layer during coating becomes better, and it tends to be easier to control to an appropriate thickness.

[0333] <Other components> The curable composition may further contain additives known in the art, such as a polymerization inhibitor, a filler, other polymer compounds, an adhesion promoter, a chain transfer agent, etc., as necessary. From the viewpoint of enhancing the dispersibility of the light scattering agent (B), the curable composition may contain an organic compound having at least one kind of group selected from the group consisting of a thiol group (-SH), a carboxyl group (-COOH), and an amino group (-NH2).

[0334] <<Method for producing curable composition>> The curable composition can be produced by a method including a step of mixing predetermined components and other components used as necessary. The method for producing the curable composition may further include a step of preparing the resin (C). Among the components contained in the curable composition, the light scattering agent (B) may be mixed with a part or all of the solvent (J) in advance and then mixed with other components.

[0335] <<Method for producing cured film>> A cured film can be obtained by carrying out a production method including a step of applying the curable composition of the present invention and a thermal curing step of thermally curing the coating film of the curable composition (hereinafter also referred to as "composition layer"). After the step of applying the curable composition, it is preferable to include an exposure step of irradiating light to the coating film of the curable composition, and it is more preferable that the thermal curing step is carried out after the exposure step.

[0336] The method for producing a cured film can include other steps than the above steps. Examples of other steps include a drying step of drying the composition layer formed by the coating step, a developing step performed on the composition layer after the exposure step, and the like.

[0337] The curable composition of the present invention can be cured at a low temperature of less than 100°C, that is, a cured film can be produced in a manufacturing process that does not include a heating step of 100°C or higher, and furthermore, the hardness of the cured film cured at such a low temperature can be improved.

[0338] The coating step is a step of coating a curable composition on a substrate to form a composition layer. Examples of coating methods include a spin coating method, a slit coating method, a slit and spin coating method, a printing method, and the like. In the printing method, the curable composition is applied through a mask provided on the substrate, and after the mask is peeled off from the substrate, the composition layer formed by the coating step is cured, whereby a cured film can be formed as a cured pattern on a part of the substrate surface.

[0339] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and those with an aluminum, silver, silver / copper / palladium alloy thin film, etc. formed on the above substrate. The substrate is preferably a glass plate, a silicon substrate, or the like.

[0340] The substrate may be one that has been subjected to a pretreatment capable of adjusting the wettability of the substrate surface. Examples of the pretreatment include solvent cleaning with alcohol or acetone, acid treatment, alkali treatment, plasma treatment, corona treatment, and the like. By selecting an appropriate pretreatment for the substrate on which the cured film is to be laminated, the coatability of the curable composition can be improved compared to an untreated substrate.

[0341] When the curable composition contains the solvent (J), it is preferable to carry out a drying step of removing volatile components such as the solvent (J) from the composition layer after the coating step. The drying step may include a heat drying (pre-baking) treatment, a reduced pressure drying treatment, or both of these. When performing heat drying, the temperature is preferably 30°C or higher and lower than 100°C, more preferably 50°C or higher and 95°C or lower. The heating time is preferably 10 seconds or longer and 60 minutes or shorter, more preferably 30 seconds or longer and 30 minutes or shorter. When performing reduced pressure drying, it is preferably carried out under a pressure of 50 Pa or higher and 150 Pa or lower in a temperature range of 20°C or higher and 25°C or lower.

[0342] The film thickness of the composition layer after the coating step or the drying step is not particularly limited and may be appropriately selected according to the film thickness of the target cured film. For example, it is 0.5 μm or more and 10 μm or less, preferably 1 μm or more and 9 μm or less, more preferably 1.5 μm or more and 7 μm or less, and still more preferably 2 μm or more and 5 μm or less. The film thickness of the finally obtained cured film may be the same as above.

[0343] Next, it is preferable to carry out an exposure step on the composition layer after the coating step or the drying step. The exposed composition layer is cured by the polymerization of the polymerizable compound (D) etc. contained in the composition layer including the preferred embodiments. As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less is preferable. When the curable composition contains a photoinitiator (E), light near 436 nm, near 408 nm, or near 365 nm may be selectively extracted by a band-pass filter from the light of the above wavelength according to the absorption wavelength of the photoinitiator (E). Specific examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc.

[0344] The exposure amount X in the exposure step is preferably 50 mJ / cm 2 or more, more preferably 80 mJ / cm 2 or more, still more preferably 100 mJ / cm 2More preferably, it is 150 mJ / cm or more. 2 or more. The exposure dose X is usually 1000 mJ / cm or less, 2 preferably 800 mJ / cm or less, 2 more preferably 700 mJ / cm or less. 2 When the exposure dose X in the exposure process is 1000 mJ / cm or less, 2 it is possible to prevent the cured film from shrinking too much, so that the proximity of the light scattering agent (B) in the film due to the shrinkage of the cured film can be prevented, and the decrease in the emitted light intensity can be prevented. The exposure dose X is the exposure dose based on a wavelength of 365 nm and can be measured using an ultraviolet integrated light meter (UIT-250, manufactured by USHIO INC.).

[0345] As an example of a method for forming a cured pattern, which is one aspect of the cured film, a photolithography method can be mentioned. The photolithography method is a method of exposing and developing a composition layer through a photomask for forming a target cured pattern. In this case, since parallel light rays can be irradiated uniformly over the entire exposure surface, and accurate alignment between the photomask and the substrate on which the composition layer is formed can be performed, it is preferable to use an exposure apparatus such as a mask aligner and a stepper.

[0346] The composition layer after the exposure process is subjected to a developing process in which it is brought into contact with a developer and developed, so that the unexposed portion of the composition layer is dissolved and removed by the developer, and a pattern is imparted to the composition layer. Examples of the developer include aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, and tetramethylammonium hydroxide, and organic solvents. The concentration in the aqueous solution of the alkaline compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Examples of the organic solvent include the same ones as the above-mentioned solvent (J). The developer may contain a surfactant. The developing method may be any of a paddle method, a dipping method, a spray method, etc. Further, the substrate may be tilted at an arbitrary angle during development.

[0347] The composition layer after the exposure process or after the development process is thermally cured (post-baked) in the thermal curing process. By the thermal curing process, the polymerization of resin (C), polymerizable compound (D), etc. including preferred embodiments can be further advanced.

[0348] The thermal curing temperature in the thermal curing process carried out after the exposure process or after the development process is less than 100 °C, preferably 95 °C or less. From the viewpoint of ensuring a predetermined or higher film hardness, the thermal curing temperature is preferably 70 °C or higher, more preferably 80 °C or higher, and still more preferably 85 °C or higher.

[0349] The thermal curing time in the thermal curing process is preferably 0.1 hr or more, more preferably 0.2 hr or more, still more preferably 0.4 hr or more, and even more preferably 0.5 hr or more. The thermal curing time is usually 2 hr or less, preferably 1.5 hr or less, and more preferably 1.2 hr or less.

[0350] The thermal curing process can be carried out in an air atmosphere or in a vacuum atmosphere. The vacuum atmosphere means a pressure range of 150 Pa or less, preferably 120 Pa or less, more preferably 100 Pa or less, and may be 50 Pa or more.

[0351] It is preferable to carry out both the above-mentioned drying (especially heat drying) process and the thermal curing process (the temperature is less than 100 °C in both cases), and it is more preferable to carry out the temperature of any process at 95 °C or less.

[0352] The Martens hardness when the cured film produced at the above-mentioned low curing temperature is measured according to the following examples is, for example, 35 MPa or more, preferably 50 MPa or more, more preferably 70 MPa or more, and the upper limit is, for example, 120 MPa or less.

[0353] <<Display device>> The cured film obtained from the curable composition of the present invention can be used as a display device together with a light source. Examples of the display device include a liquid crystal display device, an organic EL display device, or an inorganic EL display device. Specifically, the display devices described in JP-A-2006-309219, JP-A-2006-310303, JP-A-2013-15812, JP-A-2009-251129, JP-A-2014-2363, etc. can be mentioned.

[0354] In the display device, the cured film obtained from the curable composition of the present invention is used as a white (transparent, achromatic) pattern, and usually, pixels are configured in combination with a colored pattern. This colored pattern has a function of converting the wavelength of the incident light and emitting it, and may be a cured pattern of a curable composition containing a colorant (quantum dots, pigments, dyes, etc.). The display device in which the curable composition of the present invention is preferably used includes a backlight that is a blue light source and a plurality of patterns provided on the viewing side of the backlight. The patterns include a red pattern, a green pattern, and a white (transparent, achromatic) pattern that is a cured film obtained from the curable composition of the present invention. Light of the wavelength emitted from the blue light source is emitted from the white pattern. That is, the curable composition of the present invention is useful as a white (transparent, achromatic) color filter in a display device having a blue light source as a backlight.

Examples

[0355] Hereinafter, the present invention will be described in more detail with reference to examples. In the examples, “%” and “parts” are by mass% and parts by mass, respectively, unless otherwise specified. are by mass% and parts by mass, respectively, unless otherwise specified.

[0356] [Measurement of Martens hardness of cured film] Regarding the cured film formed on the substrate, a Vickers indenter was attached to a ultra-micro hardness tester (manufactured by Fischer Instruments, FISCHERSCOPE HM2000), and a load-unload test was performed in accordance with ISO 14577 to measure the load / push-in curve. The measurement temperature was room temperature. Here, the maximum test load was 0.5 mN, the holding time was 30 seconds, and the load was unloaded to 0 mN. The measurement data was processed by WIN-HCU (manufactured by Fischer Instruments) to obtain the martensite hardness (MPa). The martensite hardness was measured at three arbitrary locations, and the arithmetic mean value was obtained.

[0357] [Thickness of the cured film] It was measured by a film thickness measuring device (DEKTAKXT; manufactured by Bruker).

[0358] [Weight average molecular weight] The measurement of the weight average molecular weight (Mw) of resin (C) was carried out under the following conditions by the GPC method. Device: K2479 (manufactured by Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40 °C Solvent: Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI Standard substance for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0359] [Acid value] 3 g of the resin (C) solution was accurately weighed, dissolved in a mixed solvent of 90 g of acetone and 10 g of water, and using a 0.1 N aqueous KOH solution as the titrant, the acid value of the resin (C) solution was measured by an automatic titrator (manufactured by Hiranuma Sangyo Co., Ltd., product name: COM-555), and the acid value per gram of solid content (AV) was determined from the acid value of the solution and the solid content of the solution.

[0360] [Double bond equivalent] The double bond equivalent was determined by dividing the total mass of the curable resin by the number of moles of radically polymerizable double bonds introduced into the curable resin.

[0361] [Solid content] Approximately 1 g of the resin (C) solution was weighed into an aluminum cup, dried at 180 °C for 1 hour, and then the mass was measured. From the mass reduction amount, the solid content (mass %) of the resin (C) solution was calculated.

[0362] (Synthesis Example 1: Synthesis of Resin (C1)) 276.8 g of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 120 °C. Next, a monomer mixture consisting of 92.4 g of 2-ethylhexyl acrylate, 184.9 g of glycidyl methacrylate, and 12.3 g of dicyclopentanyl methacrylate, to which 35.3 g of t-butyl peroxy-2-ethylhexanoate (polymerization initiator) was added, was dropped into the flask from the dropping funnel over 2 hours. After completion of the dropping, the mixture was further stirred at 120 °C for 30 minutes to carry out a copolymerization reaction to produce an addition copolymer.

[0363] Thereafter, the inside of the flask was replaced with air, 93.7 g of acrylic acid, 1.5 g of triphenylphosphine (catalyst), and 0.8 g of methoquinone (polymerization inhibitor) were added to the above addition copolymer solution, and the reaction was continued at 110 °C for 10 hours. The epoxy group derived from glycidyl methacrylate was cleaved by the reaction with acrylic acid, and at the same time, a polymerizable unsaturated bond was introduced into the side chain of the polymer. Next, 24.2 g of succinic anhydride was added to the reaction system, and the reaction was continued at 110 °C for 1 hour. The hydroxyl group generated by the cleavage of the epoxy group was reacted with succinic anhydride to introduce a carboxyl group into the side chain, and a polymer (resin C1) was obtained.

[0364] Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (C1) solution having a polymer solid content of 40%.

[0365] The weight-average molecular weight Mw of the resulting copolymer was 6.2×10 3 , the acid value in terms of solid content was 35 mg-KOH / g, and the double bond equivalent was 313 g / eq.

[0366] (Synthesis Example 2: Synthesis of Resin (C2)) In the same manner as the above resin (C1), the amount of the raw material monomers was adjusted to obtain a polymer (resin (C2)). Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (C2) solution with a polymer solid content of 40%.

[0367] The weight-average molecular weight Mw of the resulting copolymer was 4.96×10 3 , the acid value in terms of solid content was 37 mg-KOH / g, and the double bond equivalent was 344 g / eq.

[0368] (Synthesis Example 3: Synthesis of Resin (C3)) In the same manner as the above resin (C1), the amount of the raw material monomers was adjusted to obtain a polymer (resin (C3)). Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (C3) solution with a polymer solid content of 40%.

[0369] The weight-average molecular weight Mw of the resulting copolymer was 4.91×10 3 , the acid value in terms of solid content was 42 mg-KOH / g, and the double bond equivalent was 514 g / eq.

[0370] (Synthesis Example 4: Synthesis of Resin (C4)) In the same manner as the above resin (C1), the amount of the raw material monomers was adjusted to obtain a polymer (resin (C4)). Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (C4) solution with a polymer solid content of 40%.

[0371] The weight-average molecular weight Mw of the resulting copolymer was 4.1×10 3 , the acid value in terms of solid content was 50 mg-KOH / g, and the double bond equivalent was 1289 g / eq.

[0372] (Preparation Example 1: Preparation of Dispersion Liquid c of Light Scattering Agent (B)) To 70 parts of titanium oxide nanoparticles (B1) (average particle diameter: approximately 0.2 μm), 3 parts of BYK-LPN21116 (manufactured by BYK-Chemie Japan) in terms of solid content and propylene glycol monomethyl ether acetate (hereinafter referred to as "PGMEA") were added so that the total amount became 100 parts, and then the mixture was stirred with a paint shaker until it was sufficiently dispersed to obtain a dispersion liquid c (solid content: 73%) of the light scattering agent (B1).

[0373] (Examples 1 to 3: Preparation of Compositions 1 to 3) The dispersion liquid c of the light scattering agent (B) and each component were mixed to prepare Compositions 1 to 3 (curable compositions) having the compositions shown in Table 1. In Table 1, the number of parts of components other than the solvent (J) indicates the value in terms of solid content conversion.

[0374]

Table 1

[0375] Polymerizable Compound (D1): Carboxy Group-Containing Polyfunctional (Meth)acrylate (trade name "Aronix (registered trademark) M-510" manufactured by Toagosei Co., Ltd.) Polymerizable Compound (D2): Ethylene Oxide-Modified Bisphenol A Diacrylate, average molecular weight Mw is 512 Polymerizable Compound (D3): Dipentaerythritol Polyacrylate (5 to 6 functional groups) Polymerization Initiator (E1): Compound represented by the following formula (EA-1)

[0376]

Chemical Formula

[0377] Ultraviolet Absorbent (Fc1): "DAINSORB T-0" manufactured by Daiwa Kasei Co., Ltd. (2-(2,4-dihydroxyphenyl)-2H-benzotriazole) Leveling Agent (H1): Polyether-Modified Silicone Oil (trade name "Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.) Dispersant (I1): BYK-LPN21116 (manufactured by BYK-Chemie Japan) Solvent (J1): PGMEA (propylene glycol monomethyl ether acetate)

[0378] (Comparative Example 1: Preparation of Composition 4) A toluene dispersion a of semiconductor particles (A1) [green-emitting InP / ZnSeS quantum dots] containing oleic acid (G1) as an organic ligand (G) was prepared. After removing toluene from the toluene dispersion a by distillation under reduced pressure, 70 parts of cyclohexyl acetate was added to 30 parts in total of the solid content (semiconductor particles (A) and organic ligand (G)) to obtain a dispersion b of semiconductor particles (A1). The dispersion b of semiconductor particles (A1), the dispersion c of the above light-scattering agent (B1), and each component were mixed to prepare Composition 4 (curable composition) having the composition shown in Table 2. In Table 2, the number of parts of components other than the solvent (J) indicates the value in terms of solid content.

[0379] (Comparative Example 2: Preparation of Composition 5) Composition 5 was prepared in the same manner as Composition 1, except that resin (C3) was used instead of resin (C1).

[0380] (Comparative Example 3: Preparation of Composition 6) Composition 6 was prepared in the same manner as Composition 1, except that resin (C4) was used instead of resin (C1).

[0381] The compositions of Compositions 4 to 6 are shown in Table 2.

[0382]

Table 2

[0383] Antioxidant (Fb1): Trade name "Sumilizer (registered trademark) GP" manufactured by Sumitomo Chemical Co., Ltd. Solvent (J2): A mixture of PGMEA (propylene glycol monomethyl ether acetate) and cyclohexyl acetate

[0384] [Test No. 1] On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.), Composition 1 obtained in Example 1 was applied by spin coating so that the film thickness after post-baking was 5 μm, and then a drying process (pre-baking) at 70 °C for 1 minute was performed to form a film of Composition 1. After cooling, using an exposure machine (UPE-1255MA; manufactured by USHIO Inc.), under an air atmosphere, light irradiation was carried out at an exposure dose of 200 mJ / cm 2 (based on 365 nm) to perform the exposure process, and a heat curing process was carried out by performing a heat curing treatment (post-baking) at 95 °C for 30 minutes to obtain a substrate having a cured film.

[0385] [Test No. 2 - 10] Except that the film thickness (μm) of the cured film and the type of the composition used were as shown in Table 3, the drying process, exposure process, and heat curing process were carried out in the same manner as in Test No. 1. For Test No. 2 - 8, substrates having cured films were obtained. Note that Test No. 9 and 10 were examples in which the composition did not cure as shown in Table 3 although the same processes as in Test No. 1 - 8 were carried out.

[0386] The measurement results are shown in Table 3.

[0387]

Table 3

Claims

1. A curable composition containing a light-scattering agent (B) and a resin (C) and not containing semiconductor particles (A), wherein a value X calculated by the following formula (1) from the acid value and the weight-average molecular weight Mw of the resin (C) is 10 or more and 59.75 or less, and the curable composition wherein the double bond equivalent of the resin (C) is 100 g / eq or more and less than 500 g / eq. X = {acid value (mg-KOH / g) × weight-average molecular weight Mw} / 10,000... (1)

2. The curable composition according to Claim 1, wherein the mass ratio (C / B) of the resin (C) to the light-scattering agent (B) is 10 or more.

3. The curable composition according to Claim 1, wherein the acid value of the resin (C) is less than 80 mg-KOH / g.

4. The curable composition according to Claim 1, wherein the weight-average molecular weight Mw of the resin (C) is 4,930 or more and 8,000 or less.

5. The curable composition according to Claim 1, further containing a polymerizable compound (D), wherein the mass ratio (C / D) of the resin (C) to the polymerizable compound (D) is 2 or more.

6. The curable composition according to Claim 1, further containing a polymerizable compound (D), wherein the polymerizable compound (D) contains a polymerizable compound having one or more cyclic hydrocarbon groups and two ethylenically unsaturated bonds in one molecule.

7. The curable composition according to Claim 6, wherein the polymerizable compound (D) further contains a polymerizable compound having an acidic functional group and three or more ethylenically unsaturated bonds in one molecule.

8. The curable composition according to Claim 1, not containing a colored colorant (K).

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