TW201840613A - Polymer and composition - Google Patents

Abstract

Provided are a polymer useful for inorganic particle dispersion and a composition that includes inorganic particles and said polymer. Provided are: a composition including inorganic particles and a polymer that has structural units (i-1) derived from a polymerizable carboxylic acid compound having an ethylenic unsaturated bond and a carboxyl group that bonds to the ethylenic unsaturated bond via a linking group; and a polymer having structural units (i-1) derived from a polymerizable carboxylic acid compound having an ethylenic unsaturated bond and a carboxyl group that bonds to the ethylenic unsaturated bond via a linking group, wherein the polymerizable carboxylic acid compound has an N-substituted maleimide structure and an acid value of at least 20 mg KOH/g and no more than 150 mg KOH/g.

Description

Polymer and composition

The present invention relates to a polymer and a composition comprising the polymer and the inorganic particles.

It is known to prepare a dispersing agent in order to enhance the dispersibility of particles such as pigments in the composition. It is disclosed in Japanese Laid-Open Patent Publication No. 2000-327946 (Patent Document 1) that, as a dispersing agent for dispersing an inorganic pigment in water, water solubility having a carboxyl group or a derivative group bonded to a molecular main chain is used. Polymer. [Prior Art Document] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2000-327946

[Problem to be Solved by the Invention] An object of the present invention is to provide a polymer which is effective for use in the dispersion of inorganic particles. Another object of the present invention is to provide a composition comprising inorganic particles and the polymer. [Means for solving the problem]

The present invention provides the compositions and polymers shown below. [1] A composition comprising: a polymer having a structural unit (i-1) derived from a polymerizable carboxylic acid compound having an ethylenically unsaturated bond and via a link a carboxyl group bonded to the ethylenically unsaturated bond; and an inorganic particle. [2] The composition according to [1], wherein the polymerizable carboxylic acid compound has an N-substituted maleimide structure. [3] The composition according to [1] or [2] wherein the polymer further has a structural unit (i-2) derived from an N-substituted maleimide compound having no carboxyl group. [4] The composition according to [3], wherein the inorganic particles comprise semiconductor quantum dots. [5] A polymer having a structural unit (i-1) derived from a polymerizable carboxylic acid compound having an ethylenically unsaturated bond and bonded to the ethyl group via a linking group The carboxyl group of the unsaturated bond, and the polymerizable carboxylic acid compound has an N-substituted maleimide structure, and the acid value is 20 mgKOH/g or more and 150 mgKOH/g or less. [Effects of the Invention]

A polymer having excellent ability to disperse inorganic particles (inorganic particle dispersibility) and a composition using the same can be provided.

<Polymer> The polymer of the present invention has a structural unit (i-1) derived from a polymerizable carboxylic acid compound (hereinafter, the polymerizable carboxylic acid compound is also referred to as "polymerizable carboxylic acid compound (I)"). The polymerizable carboxylic acid compound has an ethylenically unsaturated bond and a carboxyl group bonded to the ethylenically unsaturated bond via a linking group. The polymer may further include a structural unit other than the structural unit (i-2) and the structural unit (i-3), which will be described later. The polymer has excellent inorganic particle dispersibility and is useful as a dispersant for dispersing inorganic particles. The dispersant may be composed of the polymer or may be composed only of the polymer. In addition, the compound exemplified as the dispersing agent or each component contained or contained in the composition described later in the present specification may be used singly or in combination of plural kinds unless otherwise specified.

[1] Structural unit (i-1) The structural unit (i-1) of the polymer is a polymerizable property derived from a carboxyl group having an ethylenically unsaturated bond and bonded to the ethylenically unsaturated bond via a linking group. A structural unit of the carboxylic acid compound (I). The polymerizable carboxylic acid compound (I) may be used alone or in combination of two or more. That is, the polymer may have one structural unit (i-1), or may have two or more structural units (i-1).

The linking group contained in the polymerizable carboxylic acid compound (I) is a group in which an ethylenically unsaturated bond is bonded to a carboxyl group instead of being directly bonded. The ethylenically unsaturated bond is separated from the carboxyl group by at least one atom by the presence of a linking group. The carbon atom of the ethylenically unsaturated bond bonded to one end of the linking group and the carbon atom of the carboxyl group bonded to the other end of the linking group are usually one or more and 20 or less, preferably Two or more and 16 or less, more preferably four or more and twelve or less atoms. In the case where the number of atoms present in the spacer is zero, the desired sufficient dispersibility of the inorganic particles cannot be obtained.

The linking group may, for example, be a divalent hydrocarbon group, and the divalent hydrocarbon group is not limited to a linear chain or a branched chain, and may have a cyclic structure or a cyclic structure. One or more -CH ₂ - contained in the divalent hydrocarbon group may be -O-, -S-, -S(=O)-, -C(=O)-, -NH- or -NR ¹ -[R ¹ represents a monovalent or divalent hydrocarbon group (for example, an alkyl group or an alkylene group, etc.), and more than one -CH ₂ - contained in the hydrocarbon group may be -O-, -S-, -S(=O)- a radical substitution containing a hetero atom such as -C(=O)- or -NH- or the like containing a hetero atom. R ¹ may form a ring together with a N atom, an ethylenically unsaturated bond, and a part of a linking group to which it is bonded. The linking group is preferably one or more divalent hydrocarbon groups of -CH ₂ - which may be substituted by -O-, -C(=O)-, -NH- or -NR ¹ -.

From the viewpoint of improving the dispersibility of the inorganic particles, the carboxyl group of the structural unit (i-1) is preferably disposed at the molecular end.

The polymerizable carboxylic acid compound (I) having an N-substituted maleimide structure is preferable in terms of maintaining good inorganic particle dispersibility and improving heat resistance (thermal stability) of the polymer. In the case where the polymerizable carboxylic acid compound (I) has an N-substituted maleimide structure, the ethylenically unsaturated bond is an N-substituted maleimide structure of maleimide. A carbon-carbon double bond contained in a structural moiety (ring structure). In the case where the polymerizable carboxylic acid compound (I) has an N-substituted maleimide structure, the carboxyl group is contained in a substituent bonded to the N atom of the maleimide moiety. From the viewpoint of improving the dispersibility of the inorganic particles, the carboxyl group is preferably a terminal group disposed at a substituent bonded to the N atom.

The polymerizable carboxylic acid compound (I) having an N-substituted maleimide structure has a compound represented by the following formula.

(wherein X is a divalent linking group linking the N atom of the maleimide structure and the C atom of the carboxyl group)

The divalent linking group represented by X may be a divalent hydrocarbon group, and the divalent hydrocarbon group is not limited to a linear chain or a branched chain, and may have a cyclic structure or a cyclic structure. One or more -CH ₂ - contained in the divalent hydrocarbon group may be -O-, -S-, -S(=O)-, -C(=O)-, -NH- or -NR ² -[R ² represents a monovalent hydrocarbon group (for example, an alkyl group or the like), and one or more -CH ₂ - contained in the hydrocarbon group may be -O-, -S-, -S(=O)-, -C(=O)- Or a substituent containing a hetero atom such as -NH- or the like containing a hetero atom. The divalent linking group represented by X is preferably one or more -CH ₂ -divalent hydrocarbon groups which may be substituted by -O- or -C(=O)-, and more preferably one or more -CH ₂ - The -O- or -C(=O)-substituted linear divalent hydrocarbon group is particularly preferably a linear divalent hydrocarbon group. The carbon number of the divalent hydrocarbon group represented by X is preferably one or more and 18 or less, more preferably two or more and 14 or less, and still more preferably three or more, from the viewpoint of improving the dispersibility of the inorganic particles. And 10 or less. From the viewpoint of heat resistance (thermal stability) of the polymer, a preferred example of the divalent hydrocarbon group represented by X is -CH ₂ - a divalent hydrocarbon group which is not substituted with the hetero atom-containing group.

[2] Structural unit (i-2) The polymer may further have a structural unit (i-2) derived from an N-substituted maleimide compound having no carboxyl group. The heat resistance of the polymer can be improved by the fact that the polymer further has the structural unit (i-2). The N-substituted maleimide compound having no carboxyl group may be used alone or in combination of two or more. That is, the polymer may have one structural unit (i-2), or may have two or more structural units (i-2).

The substituent at the N position of the N-substituted maleimide compound is not particularly limited, and may be, for example, a monovalent hydrocarbon group. Examples of the monovalent hydrocarbon group include a linear, branched, cyclic alkyl group or an aromatic hydrocarbon group having 1 or more and 20 or less carbon atoms, or a combination thereof. Examples of the linear or branched alkyl group include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a second butyl group, a third butyl group, a pentyl group, a hexyl group, and an octyl group. 2-ethylhexyl and the like. The cyclic alkyl group may, for example, be a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or a cyclodecyl group. Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group. When the substituent at the N position is a group containing a cycloalkyl group or an aromatic hydrocarbon group, the heat resistance of the polymer tends to be improved.

[3] Structural unit (i-3) The polymer may further have a structural unit (i-3) as a structural unit other than the structural unit (i-1) and the structural unit (i-2). The polymer may have one structural unit (i-3), or may have two or more structural units (i-3). The structural unit (i-3) is a polymerizable carboxylic acid compound other than the polymerizable carboxylic acid compound (I) (hereinafter, the polymerizable carboxylic acid compound is also referred to as "polymerizable carboxylic acid compound (II)" a structural unit (i-3-1), a carboxyl group-free polymerizable compound other than a carboxyl group-free N-substituted maleimide compound (a compound forming the structural unit (i-2)) Structural unit (i-3-2).

Examples of the polymerizable carboxylic acid compound other than the polymerizable carboxylic acid compound (I) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, and α-(hydroxymethyl)(meth)acrylic acid; Unsaturated dicarboxylic acid such as enedic acid, fumaric acid, citraconic acid, mesaconic acid, 3,4,5,6-tetrahydrophthalic acid; maleic anhydride, citraconic anhydride, 3 An unsaturated dicarboxylic anhydride such as 4,5,6-tetrahydrophthalic anhydride or the like. The "(meth)acrylic group" referred to in the present specification means at least one selected from the group consisting of an acrylic group and a methacryl group. The same applies to the expressions of "(meth)acrylonitrile" and "(meth)acrylate".

Examples of the carboxyl group-free polymerizable compound other than the carboxyl group-free N-substituted maleimide compound include methyl (meth)acrylate, ethyl (meth)acrylate, and (meth)acrylic acid. N-butyl ester, second butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, (methyl) ) lauryl acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, (meth) acrylate Tricyclo [5.2.1.0 ^2,6 ]decane-8-yl ester (referred to as "dicyclopentyl (meth) acrylate) as a conventional name in the art. Also sometimes referred to as "tricyclodecyl (meth) acrylate", tricyclo [5.1.02 ^2,6 ]nonene-8-yl (meth) acrylate [as a customary name in the art) It is called "dicyclopentenyl (meth) acrylate", dicyclopentaoxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate , (meth) acrylate such as allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate or benzyl (meth) acrylate; a hydroxyl group-containing (meth) acrylate such as 2-hydroxyethyl (meth)acrylate or 2-hydroxypropyl (meth)acrylate; diethyl maleate or diethyl fumarate; a dicarboxylic acid diester such as 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-di Hydroxybicyclo[2.2.1]hept-2-ene, 5,6- (hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxy Bicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2- Alkene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-t-butoxy Carbonylbicyclo[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(t-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, etc. Bicyclic unsaturated compound; styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, partial Dichloroethylene, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like.

[4] Content of the structural unit The ratio of the structural unit (i-1) in the polymer is preferably such that the acid value in terms of the solid content of the resin adjusted to the polymer is preferably 20 mgKOH/g or more and 150 mgKOH/g. More preferably, it is adjusted to 40 mgKOH/g or more and 130 mgKOH/g or less, and further preferably adjusted to 60 mgKOH/g or more and 110 mgKOH/g. When the ratio of the structural unit (i-1) is in the above range, the inorganic particles have a tendency to be excellent in dispersibility. If the proportion of the structural unit (i-1) is too high, there is a possibility that the solution gels during dispersion. In the same manner as the structural unit (i-1), the ratio of the structural unit (i-2) is preferably such that the acid value in terms of the solid content of the resin adjusted to the polymer is preferably 20 mgKOH/g or more and 150 mgKOH/g or less. More preferably, it is adjusted to 40 mgKOH/g or more and 130 mgKOH/g or less, and further preferably adjusted to 60 mgKOH/g or more and 110 mgKOH/g or less. Similarly, the ratio of the structural unit (i-3) is preferably such that the acid value in terms of the solid content of the resin adjusted to the polymer is preferably 20 mgKOH/g or more and 150 mgKOH/g or less, and more preferably adjusted to 40. Above mgKOH/g and below 130 mgKOH/g.

In a preferred embodiment, the polymer is a polymer having a structural unit (i-1) derived from a polymerizable carboxylic acid compound having an ethylenically unsaturated bond and via a linking group. The carboxyl group bonded to the ethylenically unsaturated bond has a N-substituted maleimide structure, and the acid value is 20 mgKOH/g or more and 150 mgKOH/g or less. The acid value of the polymer of this embodiment is more preferably 40 mgKOH/g or more and 130 mgKOH/g or less, further preferably 60 mgKOH/g or more and 110 mgKOH/g or less.

[5] Heat resistance of polymer The polymer preferably has heat resistance (a property that is difficult to decompose when heat is applied and has good stability). The polymer preferably has a weight reduction ratio of 2.0% or less, more preferably 1.8% or less, still more preferably 1.2% or less, and particularly preferably 1.0% or less when held at 230 ° C for 30 minutes. The lower limit is not particularly limited, but is usually 0.0% or more.

The polymer preferably has a decomposition temperature of 240 ° C or higher, more preferably 260 ° C or higher, further preferably 280 ° C or higher, and particularly preferably 290 ° C or higher. The upper limit is not particularly limited and is usually 400 ° C or lower. The decomposition temperature of the polymer can be measured in the following manner. Referring to Fig. 1, using a thermogravimetric analyzer, the temperature is raised from 50 ° C to 150 ° C at a temperature increase rate of 10 ° C / min under an air flow, and then the temperature is raised from 150 ° C to 400 ° C at a temperature increase rate of 2 ° C / min. The horizontal axis is the temperature (°C), and the vertical axis is a graph showing the mass change. The intersection X of the tangent to the horizontal portion on the low temperature side and the tangent to the inflection point on the low temperature side in the obtained graph can be set as the decomposition temperature of the polymer.

[6] Method for producing a polymer The polymer can be referred to the "Experimental method for polymer synthesis" (Dazu Takashi, Chemical Co., Ltd., 1st edition, 1st printing, March 1, 1972) The method described in the above and the cited documents described in the literature are manufactured.

Specifically, a method in which a predetermined amount of a monomer component forming the structural unit, a polymerization initiator, a solvent, and the like are added to a reaction container, and the mixture is stirred, heated, and kept warm in a deoxidizing atmosphere. The polymerization initiator, the solvent and the like are not particularly limited, and are generally used by users in the field. Examples of the polymerization initiator include an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide. (benzaldehyde peroxide, etc.). The solvent may be any one as long as it dissolves each monomer.

The polystyrene-equivalent weight average molecular weight (Mw) of the polymer is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and still more preferably 5,000 or more, from the viewpoint of improving the dispersibility of the inorganic particles. Below 30000. The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the polymer is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.

<Dispersant> The dispersant contains the polymer. The dispersing agent may be composed of the polymer, and may also contain the polymer and other components. Examples of other components include solvents such as organic solvents, additives, and the like. The solvent and the additive may be the same as those described in the <curable resin composition> described later. Examples of the additive include an antioxidant, an ultraviolet absorber, a leveling agent, an anti-agglomerating agent, and an anti-settling agent.

<Composition (Constituent Containing Inorganic Particles)> The composition (the composition containing inorganic particles) of the present invention contains inorganic particles and the polymer. The composition may also be one containing inorganic particles and the dispersing agent. Since the composition contains the polymer, the inorganic particles can be excellent in dispersibility.

[1] Inorganic Particles The shape of the inorganic particles is not particularly limited, and may be spherical or substantially spherical, or may be non-spherical. Further, the inorganic particles may be hollow particles. The average particle diameter of the inorganic particles is not particularly limited, and is, for example, 0.5 nm or more and 50 μm or less.

Examples of the inorganic particles include particles containing an inorganic compound. Examples of the inorganic compound include inorganic oxides such as titanium oxide, aluminum oxide, cerium oxide, magnesium oxide, zinc oxide, and barium titanate; inorganic nitrides such as cerium nitride, boron nitride, and aluminum nitride; and magnesium fluoride. An inorganic fluoride such as calcium fluoride or an inorganic salt such as calcium carbonate or barium sulfate; glass; an inorganic semiconductor such as a semiconductor quantum dot. The inorganic particles may also be inorganic pigments.

In the conventional dispersant, it may be difficult to uniformly disperse inorganic semiconductor particles such as semiconductor quantum dots. However, the polymer or dispersant according to the present invention can be well dispersed even in the case of inorganic semiconductor particles.

The inorganic semiconductor particles are preferably luminescent (fluorescent luminescent) semiconductor particles. The luminescent semiconductor particles are particles containing a semiconductor crystal, and are preferably nanoparticles containing a semiconductor crystal. A preferred example of the luminescent semiconductor particles is a semiconductor quantum dot. The average particle diameter of the semiconductor quantum dots is, for example, 0.5 nm or more and 20 nm or less, preferably 1 nm or more and 15 nm or less (for example, 2 nm or more and 15 nm or less). The average particle diameter of the semiconductor quantum dots can be determined using a transmission electron microscope (TEM).

The semiconductor quantum dot may be, for example, comprised of a group selected from the group consisting of a Group 2 element, a Group 11 element, a Group 12 element, a Group 13 element, a Group 14 element, a Group 15 element, and a Group 16 element of the periodic table. A semiconductor material consisting of one or two or more elements.

Specific examples of the semiconductor material constituting the semiconductor quantum dot include a compound of a group 14 element and a group 16 element such as SnS ₂ , SnS, SnSe, SnTe, PbS, PbSe, and PbTe; GaN, GaP, GaAs, GaSb, InN, a compound of a Group 13 element and a Group 15 element such as InP, InAs, InSb, InGaN, InGaP; Ga ₂ O ₃ , Ga ₂ S ₃ , Ga ₂ Se ₃ , Ga ₂ Te ₃ , In ₂ O ₃ , In ₂ S ₃ , compounds of Group 13 elements and Group 16 elements such as In ₂ Se ₃ and In ₂ Te ₃ ; ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, HgO, HgS, HgSe, HgTe, etc. a compound of a group element and a group 16 element; As ₂ O ₃ , As ₂ S ₃ , As ₂ Se ₃ , As ₂ Te ₃ , Sb ₂ O ₃ , Sb ₂ S ₃ , Sb ₂ Se ₃ , Sb ₂ Te ₃ , a compound of a Group 15 element and a Group 16 element such as Bi ₂ O ₃ , Bi ₂ S ₃ , Bi ₂ Se ₃ , and Bi ₂ Te ₃ ; MgS, MgSe, MgTe, CaS, CaSe, CaTe, SrS, SrSe, SrTe, a compound of a Group 2 element such as BaS, BaSe, or BaTe and a Group 16 element; a simple substance of a Group 14 element, a Group 15 element, or a Group 16 element such as Si or Ge.

The semiconductor quantum dot may be a single layer structure including a single semiconductor material, or may be a surface of a core particle (core layer) including a single semiconductor material including a coating of one or two or more semiconductor materials different therefrom. Layer (shell) layer coated core-shell structure. In the latter case, as the semiconductor material constituting the shell layer, the band gap energy is generally larger than that of the semiconductor material constituting the core layer. Semiconductor quantum dots may also have more than two shell layers. The shape of the semiconductor quantum dot is not particularly limited, and may be, for example, a spherical shape, a substantially spherical shape, a rod shape, or a disk shape.

The semiconductor quantum dots can be those containing organic ligands coordinated to the surface of the semiconductor particles. The organic ligand disposed on the surface of the semiconductor particle may be, for example, an organic compound having a polar group exhibiting a coordination ability to a semiconductor quantum dot. The organic ligand may be an organic ligand added for the purpose of considering the synthesis of semiconductor quantum dots containing organic ligands or for the purpose of stabilizing semiconductor quantum dots.

The organic ligand may be one kind of ligand or two or more kinds of ligands. In the case where the organic ligand is an organic compound having a polar group, the organic ligand is usually coordinated to the semiconductor quantum dot via the polar group.

The polar group is preferably, for example, at least one selected from the group consisting of a thiol group (-SH), a carboxyl group (-COOH), and an amine group (-NH ₂ ). Polar groups selected from the group are advantageous in terms of improving the coordination of semiconductor quantum dots. The organic ligand may have one or more polar groups.

The molecular weight of the organic ligand to be located in the semiconductor quantum dot is not particularly limited, and may be, for example, 50 or more and 500 or less.

The organic ligand may be, for example, an organic compound represented by the following formula: YZ. In the formula, Y is the polar group, and Z is a monovalent hydrocarbon group which may contain a hetero atom (N, O, S, a halogen atom, or the like). The hydrocarbon group may have one or two or more unsaturated bonds such as a carbon-carbon double bond. The hydrocarbon group may have a linear, branched or cyclic structure. The carbon number of the hydrocarbon group is, for example, 1 or more and 40 or less, and may be 1 or more and 30 or less. The -CH ₂ - contained in the hydrocarbon group may be substituted with -O-, -S-, -C(=O)-, -NH- or the like. In terms of ease of preparation of semiconductor quantum dots, the hydrocarbon group is usually mostly free of heteroatoms.

The base Z may also contain a polar group. Regarding a specific example of the polar group, the description relating to the polar group Y can be cited. The polar group is preferably disposed at the end of the group Z. In terms of the ease of preparation of semiconductor quantum dots, the radical Z is usually mostly free of polar groups.

Examples of the organic ligand having a carboxyl group as the polar group Y include formic acid, acetic acid, propionic acid, and other saturated or unsaturated fatty acids. Examples of the saturated or unsaturated fatty acid include butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, and arachidic acid. Saturated fatty acids such as acid), behenic acid, and tetracosanoic acid; myristoleic acid, palmitoleic acid, oleic acid, icosenoic acid, Monovalent unsaturated fatty acids such as erucic acid and nervonic acid; linoleic acid, α-linolenic acid, γ-linolenic acid, stearidonic acid (stearidonic) Acid), bis-gamma-linolenic acid, arachidonic acid, eicosatetraenoic acid, docosadienoic acid, adrenic acid (adrenic acid) A polyvalent unsaturated fatty acid such as docosatetraenoic acid.

Examples of the organic ligand having a thiol group or an amine group as the polar group Y include an organic coordination in which the carboxyl group having the carboxyl group as the organic ligand of the polar group Y exemplified above is replaced with a thiol group or an amine group. child. Furthermore, if the semiconductor quantum dots contain an organic ligand, the dispersion of the semiconductor quantum dots may be improved. Among them, in consideration of the constraints on the synthesis, the organic ligand generally has a hydrocarbon chain or the like and is hydrophobic. In this case, the case where the dispersion of the semiconductor quantum dots is improved is usually a case where a non-polar solvent is used. When the polymer or dispersant of the present invention is used, the dispersibility of the semiconductor quantum dot containing the organic ligand to the polar solvent can be improved.

[2] The content of the polymer and the dispersing agent in the composition (the composition containing the inorganic particles). In a preferred embodiment of the present invention, the composition (the composition containing the inorganic particles) is 100 parts by mass based on the inorganic particles. The content of the polymer in the range of, for example, 1 part by mass or more and 100 parts by mass or less, preferably 2 parts by mass or more and 80 parts by mass or less, more preferably 4 parts by mass or more and 50 parts by mass or less. In the case where the composition contains the dispersing agent, the content of the dispersing agent in the composition is adjusted to be, for example, 1 part by mass or more based on 100 parts by mass of the inorganic particles. 100 parts by mass or less is preferably adjusted to 2 parts by mass or more and 80 parts by mass or less, and more preferably 4 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the inorganic particles. In another preferred embodiment, the content of the polymer in the composition (the composition containing the inorganic particles) is, for example, 5 parts by mass or more and 400 parts by mass or less with respect to 100 parts by mass of the inorganic particles. It is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 50 parts by mass or more and 150 parts by mass or less. In the case where the composition contains the dispersing agent, the content of the dispersing agent in the composition is adjusted to be, for example, 5 parts by mass or more based on 100 parts by mass of the inorganic particles. The amount of the inorganic particles is preferably adjusted to 10 parts by mass or more and 200 parts by mass or less, and more preferably 50 parts by mass or more and 150 parts by mass or less with respect to 100 parts by mass of the inorganic particles. As another preferred embodiment, a case where the composition is a resist composition can be mentioned.

The composition may contain other components than the inorganic particles, the polymer, and the dispersant. Examples of other components include solvents (adhesive resins), solvents such as organic solvents, and additives. The resin (binder resin), the solvent, and the additive may be the same as those described in the <curable resin composition> described later. Examples of the additive include a polymer compound other than a resin (adhesive resin), an antioxidant, an ultraviolet absorber, an adhesion promoter, a leveling agent, an anti-agglomerating agent, an organic acid, an organic amine compound, a thiol compound, a curing agent, and the like. .

<Resin Composition> The resin composition is an embodiment of the composition (a composition containing inorganic particles), and includes inorganic particles, the polymer or the dispersant, and a resin (adhesive resin). The resin composition can be applied to, for example, a substrate, dried as necessary, and then cured as necessary to form a film (coating film) containing inorganic particles. The film can be used, for example, in a use corresponding to the function of the inorganic particles contained therein. A preferred example of the inorganic particles is the semiconductor quantum dot. The inorganic particles may also be a light scattering agent, a filler, or the like.

The content of the resin (binder resin) in the solid content of the resin composition is preferably 5% by mass or more and 70% by mass or less, more preferably 10% by mass or more and 65% by mass or less, and further preferably 15% by mass or more and 60% by mass or less. The content of the inorganic particles is, for example, 0.1 parts by mass or more and 50 parts by mass or less, preferably 1 part by mass or more and 45 parts by mass or less, more preferably 5 parts by mass or more, and 40 parts by mass or less of 100 parts by mass of the solid content of the resin composition. Below the mass. The "solid content of the resin composition" means the total of components other than the solvent contained in the resin composition.

The resin composition may contain other components than inorganic particles, a polymer, a dispersant, and a resin. Examples of other components include solvents such as organic solvents, additives, and the like. The solvent and the additive may be the same as those described in the <curable resin composition> described later. Examples of the additive include a polymer compound other than a resin (adhesive resin), an antioxidant, an ultraviolet absorber, an adhesion promoter, a leveling agent, an anti-agglomerating agent, an organic acid, an organic amine compound, a thiol compound, a curing agent, and the like. .

<Curing Resin Composition> The curable resin composition is an embodiment of the resin composition, and includes inorganic particles, the polymer or the dispersant, a resin (adhesive resin), and a polymerizable compound. A preferred example of the inorganic particles is the semiconductor quantum dot. The content of the inorganic particles is, for example, 0.1 part by mass or more and 50 parts by mass or less, preferably 1 part by mass or more and 45 parts by mass or less, more preferably 5 parts by mass or more, based on 100 parts by mass of the solid content of the curable resin composition. And 40 parts by mass or less. For example, when the inorganic particles are semiconductor quantum dots, when the content of the inorganic particles is within the above range, a cured film (such as a wavelength conversion film) can have sufficient light-emitting intensity and excellent pattern formability. The "solid content of the curable resin composition" means the total of the components other than the solvent contained in the curable resin composition.

[1] Resin The curable resin composition may contain one or two or more kinds of resins. The resin is not particularly limited as long as it can form a binder resin, and when it is preferable to impart developability to a cured product of the curable resin composition, an alkali-soluble resin is preferable. The alkali solubility means a property of being dissolved in an aqueous solution of an alkali compound, that is, a developer.

Examples of the alkali-soluble resin include the following resins [K1] to [K6]. Resin [K1]: at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (a) (hereinafter also referred to as "(a)"), and having a carbon number of 2 or more and 4 or less a monomer of a cyclic ether structure and an ethylenically unsaturated bond (b) (hereinafter also referred to as "(b)"); a resin [K2]: (a) and (b) and (a) Copolymerized monomer (c) (wherein different from (a) and (b)) (hereinafter also referred to as "(c)"); resin [K3]: copolymerization of (a) and (c) Resin [K4]: a resin obtained by reacting (b) with an interpolymer of (a) and (c); resin [K5]: reacting the interpolymers of (a) and (b) with (c) Resin; Resin [K6]: A resin obtained by reacting (a) and (b) with the copolymer of (c) to further react a carboxylic anhydride.

Specific examples of (a) include: (meth)acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, and succinic acid mono [2-(methyl) propylene. Unsaturated monocarboxylic acid such as methoxyethyl ester], phthalic acid mono [2-(methyl) propylene methoxyethyl ester]; maleic acid, fumaric acid, citraconic acid, medium Kang acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrogen An unsaturated dicarboxylic acid such as phthalic acid, dimethyltetrahydrophthalic acid or 1,4-cyclohexene dicarboxylic acid; 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- Alkene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethyl Bicyclo[2.2.1]hept-2-ene and other carboxyl-containing bicyclic unsaturated compounds; maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinyl phthalic acid Dicarboxylic anhydride, 3,4,5,6-tetrahydroortylene Formic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride An unsaturated dicarboxylic anhydride such as a hemic anhydride; an unsaturated (meth)acrylic acid having a hydroxyl group and a carboxyl group in the same molecule as α-(hydroxymethyl)(meth)acrylic acid.

(b) means a cyclic ether structure having a carbon number of 2 or more and 4 or less (for example, selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) At least one of) a polymerizable compound with an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether structure having a carbon number of 2 or more and 4 or less and a (meth)acryloxy group.

(b), for example, a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter also referred to as "(b1)"), having an oxetanyl group and an ethylenic unsaturated group A single amount (b2) of a bond (hereinafter also referred to as "(b2)"), a monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter also referred to as "(b3)").

(b1), a monomer (b1-1) having a structure in which an unsaturated aliphatic hydrocarbon is epoxidized (hereinafter also referred to as "(b1-1)"), and having an unsaturated alicyclic hydrocarbon ring A single body (b1-2) of an oxidized structure (hereinafter also referred to as "(b1-2)").

Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, and glycidylvinyl Ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-inter-ethylene Glycidyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidoxymethyl)styrene, 2,4-bis(glycidoxymethyl) Styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl) Styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris (glycidyloxy) Methyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, and the like.

As (b1-2), vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; Daicel chemistry) can be cited. Industrial (manufactured by the company), 3,4-epoxycyclohexylmethyl (meth)acrylate (such as Cyclomer A400; manufactured by Daicel Chemical Industry Co., Ltd.), 3,4-(meth)acrylic acid Epoxycyclohexyl methyl ester (for example, Cyclomer M100; manufactured by Daicel Chemical Industry Co., Ltd.), 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, and the like.

The monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond is preferably a monomeric body having an oxetanyl group and a (meth) acryloxy group. Preferred examples of (b2) include 3-methyl-3-(methyl)propenyloxymethyloxetane, 3-ethyl-3-(methyl)propenyloxymethyloxalate Cyclobutane, 3-methyl-3-(methyl)propenyloxyethyloxetane, 3-ethyl-3-(methyl)propenyloxyethyloxetane.

The monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond is preferably a monomeric body having a tetrahydrofuranyl group and a (meth)acryloxy group. Preferable examples of the (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

Specific examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second butyl (meth)acrylate, and (meth)acrylic acid. Tributyl ester, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, (meth)acrylic acid ring Amyl ester, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate [This technique In the field, it is called "dicyclopentanyl (meth) acrylate" as a conventional name. Also sometimes referred to as "tricyclodecyl (meth) acrylate", tricyclo [5.1.02 ^2,6 ]nonene-8-yl (meth) acrylate [as a customary name in the art) It is called "dicyclopentenyl (meth) acrylate", dicyclopentaoxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate , (meth) acrylate such as allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate or benzyl (meth) acrylate; a hydroxyl group-containing (meth) acrylate such as 2-hydroxyethyl (meth)acrylate or 2-hydroxypropyl (meth)acrylate; diethyl maleate or diethyl fumarate; a dicarboxylic acid diester such as 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-di Hydroxybicyclo[2.2.1]hept-2-ene, 5,6- (hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxy Bicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2- Alkene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-t-butoxy Carbonylbicyclo[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(t-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene, etc. Bicyclic unsaturated compound; N-phenyl maleimide, N-cyclohexyl maleimide, N-benzyl maleimide, N-succinimide-3 - maleimide benzoate, N-succinimide-4-butyleneimine butyrate, N-succinimide-6-butylene Dicarbonyl quinone imine derivatives such as amine hexanoate, N-succinimide-3-butylimide propionate, N-(9-acridinyl) maleimide ; styrene, α-methylbenzene Ethylene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide , vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like.

Among them, (c) is preferably methyl (meth)acrylate or (meth)acrylic acid from the viewpoints of copolymerization reactivity, heat resistance of a film obtained from a self-curable resin composition, and developability at the time of pattern formation. Ethyl ester, n-butyl (meth)acrylate, benzyl (meth)acrylate, tricyclodecyl (meth)acrylate, dicyclopentenyl (meth)acrylate, styrene, N-phenyl cis Butylenediimine, N-cyclohexylmethyleneimine, N-benzyl maleimide, bicyclo[2.2.1]hept-2-ene, and the like.

In all the structural units constituting the resin [K1], the ratio of the structural unit derived from each of the resins [K1] is preferably in the following range. The structural unit derived from (a): 2 mol% or more and 50 mol% or less (more preferably 10 mol% or more and 45 mol% or less); a structural unit derived from (b), particularly derived from The structural unit of (b1): 50 mol% or more and 98 mol% or less (more preferably 55 mol% or more and 90 mol% or less).

When the ratio of the structural unit of the resin [K1] is in the above range, the storage stability of the resin, the developability of the film obtained from the curable resin composition, and the solvent resistance tend to be excellent.

Resin [K1] can be referred to the method described in the "Experimental Method for Polymer Synthesis" (Dazu Takashi, Chemical Tongren Publishing Co., Ltd., 1st Edition, 1st Printing, March 1, 1972). Manufactured by referenced documents described in the literature.

Specifically, a method in which a predetermined amount of (a) and (b) (particularly (b1)), a polymerization initiator, a solvent, and the like are added to a reaction container, and the mixture is stirred, heated, and kept warm in a deoxidizing environment . The polymerization initiator, the solvent and the like are not particularly limited, and are generally used by users in the field. Examples of the polymerization initiator include an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide. (benzaldehyde peroxide, etc.). The solvent may be any one that dissolves each monomer, and an organic solvent or the like described later may also be used.

Further, the obtained copolymer may be directly used as a solution after the reaction, or a concentrated or diluted solution may be used, or a solid (powder) may be used as a extractor by a method such as reprecipitation.

In all the structural units constituting the resin [K2], the ratio of the structural unit derived from each of the resins [K2] is preferably in the following range. The structural unit derived from (a): 4 mol% or more and 45 mol% or less (more preferably 10 mol% or more and 30 mol% or less); a structural unit derived from (b), particularly derived from The structural unit of (b1): 2 mol% or more and 95 mol% or less (more preferably 5 mol% or more and 80 mol% or less); structural unit derived from (c): 1 mol% or more and 65 mol% or less (more preferably 5 mol% or more and 60 mol% or less).

When the ratio of the structural unit of the resin [K2] is in the above range, the storage stability of the resin, the developability of the film obtained from the curable resin composition, the solvent resistance, the heat resistance, and the mechanical strength tend to be excellent.

The resin [K2] can be produced in the same manner as the method described in the production method of the resin [K1]. Specifically, a predetermined amount of (a), (b) (particularly (b1)) and (c), a polymerization initiator and a solvent are added to the reaction container, and the mixture is stirred and heated in a deoxidizing atmosphere. The method of insulation. The obtained copolymer may be used as it is, or a concentrated or diluted solution may be used, or a solid (powder) may be used as a extractor by a method such as reprecipitation.

In all the structural units constituting the resin [K3], the ratio of the structural unit derived from each of the resins [K3] is preferably in the following range. The structural unit derived from (a): 2 mol% or more and 55 mol% or less (more preferably 10 mol% or more and 50 mol% or less); structural unit derived from (c): 45 mol% The above is 98% by mole or less (more preferably 50% by mole or more and 90% by mole or less).

The resin [K3] can be produced in the same manner as the method described in the production method of the resin [K1].

The resin [K4] can be produced by obtaining the copolymer of (a) and (c), and having (b) a cyclic ether structure having a carbon number of 2 or more and 4 or less, particularly (b1) The oxirane ring is added to the carboxylic acid and/or carboxylic anhydride having (a). Specifically, first, an interpolymer of (a) and (c) is produced in the same manner as the method described as a method for producing the resin [K1]. In this case, in all the structural units constituting the copolymer of (a) and (c), the ratio derived from each structural unit is preferably in the following range. The structural unit derived from (a): 5 mol% or more and 50 mol% or less (more preferably 10 mol% or more and 45 mol% or less); structural unit derived from (c): 50 mol% The above is 95% by mole or less (more preferably 55% by mole or more and 90% by mole or less).

Next, (b) a cyclic ether structure having a carbon number of 2 or more and 4 or less, particularly an oxirane ring of (b1) and a carboxylic acid derived from (a) in the copolymer and/or Or a part of the carboxylic anhydride is reacted. Specifically, following the manufacture of the interpolymers of (a) and (c), the environment inside the flask is replaced with nitrogen from air, (b) (particularly (b1)), carboxylic acid or carboxylic anhydride and cyclic ether. A reaction catalyst (for example, tris(dimethylaminomethyl)phenol) or a polymerization inhibitor (for example, hydroquinone) is placed in a flask at 60 ° C or higher and 130 ° C or lower for 1 hour. The reaction is carried out above and for a reaction time of 10 hours or less, whereby the resin [K4] can be obtained.

With respect to (a) 100 mol, the amount of use of (b), particularly (b1), is preferably 5 mol or more and 80 mol or less, more preferably 10 mol or more and 75 mol or less. In this range, the balance between the storage stability of the resin, the developability of the film obtained from the curable resin composition, the solvent resistance, the heat resistance, the mechanical strength, and the sensitivity tends to be good. (b) used as the resin [K4] is preferably (b1), more preferably (b1-1), in the case where the reactivity of the cyclic ether structure is high and it is difficult to remain unreacted (b).

The amount of the reaction catalyst used is preferably 0.001% by mass or more and 5% by mass or less based on the total amount of (a) and (b) (particularly (b1)) and (c). The amount of the polymerization inhibitor to be used is preferably 0.001% by mass or more and 5% by mass or less based on the total amount of (a), (b), and (c).

The reaction conditions such as the addition method, the reaction temperature, and the time can be appropriately adjusted in consideration of the heat generation amount of the production equipment or the polymerization. Further, similarly to the polymerization conditions, the addition method or the reaction temperature can be appropriately adjusted in consideration of the production equipment or the calorific value of the polymerization.

Regarding the resin [K5], as a first stage, an interpolymer of (b) (particularly (b1)) and (c) was obtained in the same manner as in the production method of the resin [K1]. Similarly to the above, the obtained copolymer may be directly used as a solution after the reaction, or a concentrated or diluted solution may be used, or a solid (powder) may be used as a extractor by a method such as reprecipitation.

The ratio of the structural unit derived from (b) (particularly (b1)) and (c) is preferably in the following range with respect to the total number of moles of all the structural units constituting the copolymer. The structural unit derived from (b), particularly the structural unit derived from (b1): 5 mol% or more and 95 mol% or less (more preferably 10 mol% or more and 90 mol% or less); The structural unit of (c): 5 mol% or more and 95 mol% or less (more preferably 10 mol% or more and 90 mol% or less).

Further, under the same conditions as the method for producing the resin [K4], the (a) carboxylic acid or carboxylic acid anhydride and (b) (particularly (b1)) and (c) copolymer are derived from (b) The cyclic ether structure is reacted, whereby the resin [K5] can be obtained. The amount of (a) to be reacted with the copolymer is preferably 5 mol or more and 80 mol or less with respect to (b) (particularly (b1)) 100 mol. (b) used as the resin [K5] is preferably (b1), more preferably (b1-1), in the case where the reactivity of the cyclic ether structure is high and it is difficult to remain unreacted (b).

The resin [K6] is a resin obtained by further reacting a carboxylic anhydride with a resin [K5]. The carboxylic acid anhydride and the hydroxyl group produced by the reaction of the cyclic ether structure with a carboxylic acid or a carboxylic anhydride are reacted.

Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, and 3,4,5,6-tetra. Hydrogen phthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]heptan-2- An alkenic anhydride (nadic anhydride) or the like.

The acid value of the solution of the resin is preferably 5 mgKOH/g or more and 180 mgKOH/g or less, more preferably 10 mgKOH/g or more and 100 mgKOH/g or less, further preferably 12 mgKOH/g or more and 50 mgKOH/g or less. . The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

The polystyrene-equivalent weight average molecular weight of the resin is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, still more preferably 5,000 or more and 30,000 or less. When the molecular weight is in the above range, the solubility of the unexposed portion in the developer is high, and the residual film ratio or hardness of the obtained pattern tends to be high. The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.

The content of the resin is preferably 5% by mass or more and 70% by mass or less, more preferably 10% by mass or more and 65% by mass or less, and still more preferably 15% by mass, based on 100% by mass of the solid content of the curable resin composition. The above is 60% by mass or less. When the content of the resin is in the above range, the solubility of the unexposed portion in the developer tends to be high.

[2] The polymerizable compound contained in the polymerizable compound curable resin composition is not particularly limited as long as it is a compound which can be polymerized by an active radical generated from a polymerization initiator or the like by light irradiation or the like. A compound having a polymerizable ethylenically unsaturated bond or the like is listed. The curable resin composition may contain one or two or more kinds of polymerizable compounds.

The weight average molecular weight (Mw) of the polymerizable compound is preferably 3,000 or less. Among them, the polymerizable compound is preferably a photopolymerizable compound having three or more ethylenically unsaturated bonds. Examples of the photopolymerizable compound having three or more ethylenically unsaturated bonds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate. , dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, pentaerythritol deca (meth) acrylate , pentaerythritol nine (meth) acrylate, tris(2-(methyl) propylene oxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol 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 is modified with dipentaerythritol hexa(meth) acrylate or the like.

The content of the polymerizable compound is preferably 20 parts by mass or more and 150 parts by mass or less, more preferably 80 parts by mass or more and 120 parts by mass or less based on 100 parts by mass of the resin (binder resin) in the curable resin composition.

[3] Polymerization initiator The curable resin composition may contain a polymerization initiator. The polymerization initiator is not particularly limited as long as it is a compound capable of generating an active radical, an acid or the like by light or heat and starts to polymerize, and a known polymerization initiator can be used.

Examples of the polymerization initiator include an anthraquinone compound such as an O-indenyl hydrazine compound, a phenylalkyl ketone compound, a biimidazole compound, a triazine compound, and a fluorenylphosphine oxide compound. The curable resin composition may contain one or two or more kinds of polymerization initiators in consideration of sensitivity, pattern formability, and the like. In terms of sensitivity and precise correction of the pattern shape having a desired line width, the polymerization initiator preferably contains an anthracene compound such as an O-indenyl group compound.

The O-mercaptopurine compound is a compound having a structure represented by the following formula (d). Hereinafter, * indicates a keying key.

As the O-indenyl ruthenium compound, N-benzylideneoxy-1-(4-phenylthiophenyl)butan-1-one-2-imine, N-benzylideneoxy group- 1-(4-Phenylthiophenyl)octane-1-one-2-imine, N-benzylideneoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane- 1-keto-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]ethane-1 -imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolane A Benzyloxy)benzimidyl}-9H-indazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzene Mercapto)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzylidene-1-(9-ethyl-6-(2-methyl) Benzyl hydrazino)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyl methoxy-1-[4-(2-hydroxyethyl) Benzyl)phenylthiophenyl]propan-1-one-2-imine, N-ethinyloxy-1-[4-(1-methyl-2-methoxyethoxy)- 2-methylphenyl]-1-(9-ethyl-6-nitro-9H-indazol-3-yl)methane-1-imine and the like. Irgacure (registered trademark) OXE01, Irgacure OXE02, Irgacure OXE03 (above BASF), N-1919, NCI-930, NCI can also be used. -831 (The above is manufactured by ADEKA). These O-mercaptopurine compounds are advantageous in terms of improving lithographic performance.

The phenylalkyl ketone compound is a compound having a partial structure represented by the following formula (d4) or a partial structure represented by the following formula (d5). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a structure represented by the formula (d4) include 2-methyl-2-morpholinyl-1-(4-methylthiophenyl)propan-1-one and 2-dimethyl group. Amino-1-(4-morpholinylphenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl] 1-[4-(4-morpholinyl)phenyl]butan-1-one and the like. Commercial products such as Irgacure (registered trademark) 369, Irgacure 907, and Irgacure 379 (manufactured by BASF Corporation) can also be used.

Examples of the compound having a structure represented by the formula (d5) include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1-[4- (2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1- Olefin of ketone, α,α-diethoxyacetophenone, benzoin dimethyl ketal, and the like.

In terms of sensitivity, the phenylalkyl ketone compound is preferably a compound having a structure represented by the formula (d4).

As the biimidazole compound, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-di) Chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, see Japanese Patent Laid-Open No. Hei 6-75372, Japanese Patent Laid-Open No. Hei 6-75373, etc.), 2, 2'- Bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-four (alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2' - bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. Sho 48-38403, Japanese Patent Laid-Open No. 62 An imidazole compound in which a phenyl group at the 4,4', 5, 5'-position is substituted with an alkoxycarbonyl group (for example, see Japanese Patent Laid-Open Publication No. Hei 7-10913, etc.).

Among them, the biimidazole compound is preferably a compound represented by the following formula or a mixture thereof.

As the triazine compound, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(trichloromethane) are exemplified. 6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperidin-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)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethylene 1,1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1 , 3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc. .

The fluorenylphosphine oxide compound may, for example, be 2,4,6-trimethylbenzimidyldiphenylphosphine oxide.

Further, examples of the polymerization initiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether and other benzoin compounds; benzophenone, o-benzylidene benzoic acid methyl ester, 4- Phenylbenzophenone, 4-benzylidene-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(t-butylperoxycarbonyl)benzophenone, 2 a benzophenone compound such as 4,6-trimethylbenzophenone; a quinone compound such as 9,10-phenanthrenequinone, 2-ethylhydrazine, camphorquinone; 10-butyl-2-chloroacridone Benzene oxime, methyl phenylglyoxylate, titanium titanate compound, and the like. These are preferably used in combination with a polymerization initiation aid (particularly an amine) to be described later.

The polymerization initiator preferably contains at least one selected from the group consisting of a phenylalkyl ketone compound, a triazine compound, a fluorenyl phosphine oxide compound, an O-mercapto fluorene compound, and a biimidazole compound. The initiator is more preferably a polymerization initiator containing an O-mercaptopurine compound.

The content of the polymerization initiator is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 25 parts by mass or less, based on 100 parts by mass of the total of the resin (binder resin) and the polymerizable compound. Further, it is preferably 1 part by mass or more and 20 parts by mass or less. When the content of the polymerization initiator is within the above range, the sensitivity is high and the exposure time tends to be shortened, so that the productivity of the cured film tends to be improved.

[4] Polymerization Starting Aid The curable resin composition may contain a polymerization starting aid. The polymerization initiation aid is a compound or a sensitizer for promoting polymerization of a polymerizable compound which has started polymerization by a polymerization initiator. In the case of containing a polymerization initiator, it is used in combination with a polymerization initiator. The curable resin composition may contain one or two or more kinds of polymerization starting assistants.

Examples of the polymerization initiation aid include an amine compound, an alkoxy fluorene compound, a thioxanthone compound, and a carboxylic acid compound. Among them, a thioxanthone compound is preferred.

The amine compound may, for example, be triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate or 4-dimethyl group. Isoamyl benzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4 '-Bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-double (Ethylmethylamino)benzophenone or the like, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

As the alkoxy ruthenium compound, 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl- 9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, and the like.

As the thioxanthone compound, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1- Chloro-4-propoxythioxanthone and the like.

Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, and methoxyphenylthio group. Acetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, Naphthyloxyacetic acid and the like.

The content of the polymerization initiation aid is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less based on 100 parts by mass of the total of the resin (adhesive resin) and the polymerizable compound. the following. When the content of the polymerization initiator is within the above range, the productivity of the cured film can be further improved.

[5] Solvent The curable resin composition may contain a solvent. The solvent is preferably an organic solvent. The curable resin composition may contain one kind or two or more kinds of solvents. Examples of the solvent include an ester solvent (a solvent containing -C(=O)-O-), an ether solvent other than the ester solvent (a solvent containing -O-), and an ether ester solvent (including -C(=O)-O). - a solvent with -O-), a ketone solvent other than an ester solvent (a solvent containing -C(=O)-), an alcohol solvent, an aromatic hydrocarbon solvent, a guanamine solvent, dimethyl hydrazine or the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. , butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, acetic acid Cyclohexyl ester, 2-methylcyclohexyl acetate, cyclohexyl propionate, cis-3,3,5-trimethylcyclohexyl acetate, 4-tert-butylcyclohexyl acetate, butyric acid Ester, isopropyl cyclohexanecarboxylate, γ-butyrolactone, and the like.

Examples of the ether solvent 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, and two. Ethylene 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, diethyl Diol dibutyl ether, anisole, phenethyl ether, methyl anisole, methoxycyclohexane, and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethyl ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol Ethyl acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether Acid ester, dipropylene glycol methyl ether acetate, and the like.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, and 4-methyl-2- Pentanone, cyclopentanone, 2-ethenylcyclopentanone, cyclohexanone, 2-ethenylcyclohexanone, isophorone, and the like.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin. Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene. Examples of the guanamine solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

In terms of coatability and drying property, the solvent preferably comprises a solvent selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, and ethylene glycol. Methyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2 -pentanone, N,N-dimethylformamide, cyclohexyl acetate, methoxycyclohexane, isopropyl cyclohexanecarboxylate, cyclopentanone, cyclohexanone, cyclohexanol, benzene, At least one selected from the group consisting of toluene, xylene and mesitylene, more preferably comprising selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3 -methoxybutyl acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, cyclohexyl acetate, methoxycyclohexane, isopropyl cyclohexanecarboxylate At least one of the group consisting of ester, cyclopentanone, cyclohexanone, and cyclohexanol.

The content of the solvent is preferably 60% by mass or more and 95% by mass or less, and more preferably 65% by mass or more and 92% by mass or less, based on 100% by mass of the curable resin composition. In other words, the solid content of the curable resin composition is preferably 5% by mass or more and 40% by mass or less, more preferably 8% by mass or more and 35% by mass or less. When the content of the solvent is in the above range, the coating property of the curable resin composition and the flatness during coating tend to be good, and when the inorganic particles are semiconductor quantum dots, the light-emitting properties of the cured film become good. Propensity.

[6] Leveling agent The curable resin composition may contain a leveling agent. The curable resin composition may contain one or two or more leveling agents. Examples of the leveling agent include an anthrone-based surfactant (having no fluorine atom), a fluorine-based surfactant, and an anthrone-based surfactant having a fluorine atom. These may also have a polymerizable group in the side chain.

Examples of the anthrone-based surfactant include a surfactant having a decane bond in the molecule. Specific examples include Toray silicone DC3PA, Toray silicone SH7PA, Toray silicone DC11PA, Toray silicone SH21PA, Toray 矽Toray silicone SH28PA, Toray silicone SH29PA, Toray silicone SH30PA, Toray silicone SH8400 (trade name; Toray Dow Corning) )), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Mitto Advanced Materials, Japan) (made by Momentive Performance Materials Japan), etc.

Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Specific examples include: Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M), Megafac (registered trademark) F142D, and Megafac ) F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (made by Dickson (DIC)), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop ) EF352 (Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (Asahi Glass) (manufacturing) and E5844 (manufactured by Daikin Fine Chemicals Research Institute).

Examples of the anthrone-based surfactant having a fluorine atom include a surfactant having a decane bond and a fluorocarbon chain in the molecule. Specific examples include Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (Di Aisheng) Manufacturing) and so on.

The content of the leveling agent in the curable resin composition is usually 0.001% by mass or more and 0.2% by mass or less, preferably 0.002% by mass or more and 0.1% by mass or less, more preferably 0.005% by mass or more and 0.05% by mass. Below mass%.

[7] Antioxidant The curable resin composition may contain an antioxidant. Thereby, the heat resistance and light resistance of the curable resin composition can be improved. The curable resin composition may contain one or two or more kinds of antioxidants. The antioxidant which is generally used in the industry is not particularly limited, and examples thereof include a phenol-based antioxidant, a phosphorus-based antioxidant, and a sulfur-based antioxidant.

The phenolic antioxidant may, for example, be Iglesias (registered trademark) 1010 (Irganox 1010: pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], BASF (manufactured by BASF), Escalus 1076 (Irganox 1076: octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, manufactured by BASF ), Igola 1330 (Irganox 1330:3,3',3'',5,5',5''-hexa-t-butyl-α,α',α''-(mesitylene- 2,4,6-triyl)tri-p-cresol, manufactured by BASF (French), Iganos 3114 (Irganox 3114: 1,3,5-tris(3,5-di-t-butyl-) 4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF (Fly), Irgars 3790 (Irganox 3790:1, 3,5-tris((4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H )-trione, manufactured by BASF Co., Ltd., Irgas 1035 (Irganox 1035: thiodiethylene bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate ], BASF (manufactured by BASF), Escalus 1135 (Irganox 1135: phenylpropionic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxyl , C7-C9 side chain alkyl ester, BASF (manufactured by BASF), Escalus 1520L (Irganox 1520L: 4,6-bis (octylthiomethyl)-o-cresol, manufactured by BASF) Gales 3125 (Irganox 3125, manufactured by BASF), 易加乐斯 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy-3', 5'-di -T-butylanilino)-1,3,5-triazine, manufactured by BASF Co., Ltd., Adekastab (registered trademark) AO-80 (Adekastab AO-80:3,9- Bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoxy)-1,1-dimethylethyl)-2,4,8,10 - tetraoxaspiro(5,5)undecane, manufactured by Adico (share), Sumilizer (registered trademark) BHT, Sumilizer GA-80, Sumilai Sumilizer GS (above manufactured by Sumitomo Chemical Co., Ltd.), Chanox (registered trademark) 1790 (Cyanox 1790, manufactured by Cytec), and Vitamin E (Eisai) ) (share) manufacturing) and so on.

Examples of the phosphorus-based antioxidant include Isofoss (registered trademark) 168 (Igrafos 168: (2,4-di-t-butylphenyl) phosphite triester, manufactured by BASF), and Foss 12 (Igrafos 12: tris[2-[[2,4,8,10-tetra-t-butyldibenzo[d,f][1,3,2]dioxaphosphin-6-yl) ]oxy]ethyl]amine, manufactured by BASF (Fly), Igfos 38 (Igrafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methyl phosphite) Phenyl)ethyl ester, manufactured by BASF, Adekastab (registered trademark) 329K, Adekastab PEP36, Adekastab PEP-8 ( The above is manufactured by Eddy Co., Sandstab P-EPQ (manufactured by Clariant), Weston (registered trademark) 618, Weston 619G (above manufactured by GE), Utraranox 626 (manufactured by GE), Sumilizer (registered trademark) GP (6-[3-(3-tert-butyl) 4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyl And [d, f] [1,3,2] hept-dioxaphosphinin England) (manufactured by Sumitomo Chemical (shares)) and the like.

Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate or distearyl thiodipropionate; A β-alkylmercaptopropionate compound of a polyhydric alcohol such as methylene (3-dodecylthio)propionate] methane or the like.

[8] The other component of the curable resin composition may contain one or two or more kinds of resins (adhesive resins), polymer compounds, adhesion promoters, ultraviolet absorbers, anti-agglomerates, organic acids, and organic amines. Additives such as compounds, thiol compounds, and hardeners.

Examples of the polymer compound other than the resin (adhesive resin) include polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, and polyfluoroalkyl acrylate.

Examples of the adhesion promoter include vinyl trimethoxy decane, vinyl triethoxy decane, vinyl tris(2-methoxyethoxy) decane, and N-(2-aminoethyl)-3. -Aminopropylmethyldimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, 3-shrinkage Glycidoxypropyltrimethoxydecane, 3-glycidoxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 3-chloropropyl Methyldimethoxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethoxydecane, and the like.

Examples of the ultraviolet absorber include a benzotriazole compound such as 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole; 2-hydroxy-4. - benzophenone-based compound such as octyloxybenzophenone; benzene such as 2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate a formate compound; a triazine compound such as 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexyloxyphenol. Examples of the anti-agglomeration agent include sodium polyacrylate.

Examples of the curing agent include a compound which can react with a carboxyl group in a resin by heating to crosslink the resin, a compound which can be polymerized and cured, and the like. Specific examples thereof include an epoxy compound and an oxetane compound. Wait.

[9] Preparation method of curable resin composition The curable resin composition can be prepared by mixing inorganic particles, a polymer or a dispersant, a resin, a polymerizable compound, a usual solvent, and other components used as needed. preparation. A method of preparing a curable resin composition by mixing inorganic particles with a polymer, a dispersing agent, and a solvent to prepare a dispersion in which inorganic particles are dispersed, and mixing the dispersion with the remaining components is an example of a preferable production method.

Furthermore, the semiconductor quantum dots having organic ligands as the inorganic particles may be, for example, preparing or preparing semiconductor quantum dots coordinated with organic ligands, and then performing organic ligands on the semiconductor quantum dots. The ligand with reduced coordination amount is reduced in processing. The ligand reduction treatment can be, for example, a treatment in which an appropriate solvent is used to extract an organic ligand coordinated to a semiconductor quantum dot.

<Film formed of resin composition and curable resin composition> A film (coating film) can be formed by drying a film (layer) containing a resin composition as needed, and if necessary, curing. In addition, a cured film can be obtained by drying a film (layer) containing a curable resin composition as needed and then curing it. At this time, the patterned cured film can be obtained by patterning by a method such as photolithography, inkjet method, or printing method. The pattern forming method is preferably a photolithography method. The photolithography method is a method in which a curable resin composition is applied onto a substrate, dried to form a curable resin composition layer, and the curable resin composition layer is exposed and developed through a mask.

As the substrate, quartz glass, borosilicate glass, alumina silicate glass, or a glass plate such as soda lime glass coated with cerium oxide on the surface; or polycarbonate, polymethyl methacrylate, or poly A resin plate such as ethylene terephthalate; ruthenium; an aluminum, silver, silver/copper/palladium alloy film or the like formed on the substrate.

The formation of the patterned cured film by photolithography can be carried out under known or conventional apparatus or conditions, for example, in the following manner. First, the curable resin composition is applied onto a substrate, and dried by heating (prebaking) and/or drying under reduced pressure to remove a volatile component such as a solvent, followed by drying to obtain a curable resin composition layer. Examples of the coating method include a spin coating method, a slit coating method, a slit, and a spin coating method.

The temperature at the time of heat drying is preferably 30 ° C or more and 120 ° C or less, more preferably 50 ° C or more and 110 ° C or less. The heating time is preferably 10 seconds or longer and 10 minutes or shorter, more preferably 30 seconds or longer and 5 minutes or shorter. In the case of drying under reduced pressure, it is preferably carried out at a pressure of 50 Pa or more and 150 Pa or less at a temperature of 20 ° C or more and 25 ° C or less. The film thickness of the curable resin composition layer is not particularly limited, and can be appropriately selected depending on the desired film thickness of the cured film.

Next, exposure is performed by interposing the curable resin composition layer on a mask for forming a desired pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use can be used. As the light source used for the exposure, a light source that generates light having a wavelength of 250 nm or more and 450 nm or less is preferable. For example, for light less than 350 nm, use a filter that cuts off this wavelength range to cut off, or for light near 436 nm, near 408 nm, around 365 nm, use a bandpass filter that extracts those wavelength ranges for selection. Sexual extraction. Examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, and a halogen lamp.

In the exposure, in order to uniformly illuminate the entire exposed surface, or to accurately position the substrate with the substrate on which the curable resin composition layer is formed, it is preferable to use a mask aligner and a stepper. Equal exposure device.

The curing is performed by bringing the curable resin composition layer after the exposure into contact with the developing solution to form a pattern of the curable resin composition layer on the substrate. By development, the unexposed portion of the curable resin composition layer is dissolved in the developer to be removed. The developer is preferably an aqueous solution of a basic compound such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate or tetramethylammonium hydroxide. The concentration of the basic compound in the aqueous solution 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. The developer may further comprise a surfactant. Examples of the development method include a liquid coating method, a dipping method, a spray method, and the like. Further, the substrate may be inclined at an arbitrary angle during development. After development, it is preferably washed with water.

It is preferred to post-bake the pattern of the obtained curable resin composition layer. The post-baking temperature is preferably 60 ° C or more and 250 ° C or less, more preferably 110 ° C or more and 240 ° C or less. The post-baking time is preferably 1 minute or more and 120 minutes or less, more preferably 10 minutes or more and 60 minutes or less. The film thickness of the cured film after post-baking is, for example, 1 μm or more and 10 μm or less, preferably 3 μm or more and 10 μm or less.

The coating film formed of the resin composition or the cured film formed of the curable resin composition and the patterned cured film can be applied, for example, to applications corresponding to the functions of the inorganic particles contained therein. For example, in the case where the inorganic particles are semiconductor quantum dots or coloring pigments such as inorganic pigments, the coating film, the cured film, and the patterned cured film may be suitably used to emit wavelengths different from the wavelength of incident light. Light wavelength conversion film (wavelength conversion filter). The wavelength conversion film can be suitably used in a display device such as a liquid crystal display device or an organic electroluminescence (EL) device. Since the polymer and the dispersing agent of the present invention are excellent in dispersibility of inorganic particles, the wavelength conversion film can exhibit excellent luminescent properties. In particular, the cured film formed by the curable resin composition containing the polymer or dispersant of the present invention and the semiconductor quantum dot and the patterned cured film can uniformly disperse the semiconductor quantum dots, and thus can be desired for display. In the wavelength range, the color reproduction of the fluorescent light is excellent, and the light emission uniformity is excellent.

Further, in the case where the inorganic particles are light scattering agents, the coating film, the cured film, and the patterned cured film may be used as the light scattering layer. The wavelength conversion film may also contain a light scattering agent, whereby the light-emitting characteristics of the wavelength conversion film can be improved. [Examples]

Hereinafter, the present invention will be more specifically described by the examples, but the present invention is not limited by the examples. In the examples, the % and the parts indicating the content or the amount used are based on mass unless otherwise specified.

<Comparative Example 1> (1) Preparation of a polymer 450 parts of propylene glycol monomethyl ether acetate (PGMEA) was placed in a flask equipped with a cooling tube and a stirrer, and replaced with nitrogen. While stirring at 70 ° C, 89 parts of methyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of methacrylic acid, and 2,2'-azobis (2, 4) were added dropwise at the same temperature for 30 minutes. - dimethyl valeronitrile (manufactured by Wako Pure Chemical Industries, Ltd.) 6 parts, pentaerythritol tetrakis(3-mercaptopropionate) [PEMP] (manufactured by SC Organic Chemical Co., Ltd.) 6 parts and 450 parts of PGMEA mixed solution, The polymerization was carried out for 2 hours at the same temperature. After slowly cooling the reaction solution to room temperature, it was added dropwise to ethanol, and the precipitate was collected by filtration, and dried by a vacuum dryer at 40 ° C to obtain a white powder of a polymer (dispersant). Hereinafter, this polymer is referred to as a polymer H1.

The polymer H1 has the following structural unit.

(2) Preparation of a composition Core-shell type semiconductor quantum dot INP530 having a structure of InP (nucleus) / ZnS (first shell) / ZnS (second shell) was prepared [manufactured by NN-LABS] . An oleylamine is coordinated to the surface of the semiconductor quantum dot. Regarding the semiconductor quantum dot (QD), a solvent replacement treatment is performed by the following procedure. First, a volume fraction of hexane 2 was added to a volume fraction of the dispersion containing the QD to carry out dilution. Thereafter, 30 parts by volume of ethanol was added to precipitate QD, and the mixture was centrifuged. The supernatant was removed, and a volume fraction of hexane was added to redisperse the QD. This treatment was carried out three times in total (precipitation by centrifugal addition + centrifugation ® supernatant removal ® redispersion by addition of hexane). In the third redispersion, cyclohexyl acetate was added instead of hexane so that the concentration of QD (including an oleylamine complex) was 20% by mass to obtain a QD dispersion.

20 parts of the powder of the polymer H1 obtained in the above (1), 40 parts of PGMEA and 40 parts of CHXA were mixed to prepare a polymer solution. In addition, 20 parts of an antioxidant (Sumilizer (registered trademark) GP) manufactured by Sumitomo Chemical Co., Ltd., and 80 parts of PGMEA were mixed to prepare an antioxidant solution.

25.0 parts of the QD dispersion, 14.0 parts of the polymer solution, and 1.9 parts of the antioxidant solution were placed in a flask, and the mixture was stirred under heating at 120 ° C for 12 hours, and then left to cool to room temperature to obtain a composition.

(3) Measurement of Weight Average Molecular Weight Mw of Polymer The weight average molecular weight Mw of the polymer H1 obtained in the above (1) (standard polyphenylene obtained by gel permeation chromatography (GPC)) Ethylene conversion value). The results are shown in Table 1. The measurement of the weight average molecular weight Mw was carried out under the following conditions by a GPC method. Device: HLC-8120GPC (manufactured by Tosoh), column: PLgel mixC+ protection column (GuardColumn), column temperature: 40 ° C, solvent: dimethyl formamide (DMF) (30 mM LiBr, 10 mM H ₃ PO ₄ ), flow rate: 1.0 mL/min, solid concentration of the test liquid: 0.001% by weight to 0.01% by weight, injection amount: 100 μL, detector: refractive index (refractive) Index, RI)-8020/ultraviolet (UV)-8020 (254 nm), standard material for calibration: TSK STANDARD POLYSTYRENE F-128, F-40, F-10, F-4 , F-1, A-5000 (made by Tosoh Co., Ltd.).

(4) Evaluation of heat resistance of polymer The decomposition temperature of the polymer was measured in accordance with the following. 30 mg of the powder of the polymer H1 obtained in the above (1) was weighed into an aluminum frying pan, and a thermogravimetric analyzer "TGDTA6200" (manufactured by Seiko Instrument Co., Ltd.) was used at 10 ° C under an air flow. The temperature rise rate of the minute was raised from 50 ° C to 150 ° C, and then the temperature was raised from 150 ° C to 400 ° C at a temperature increase rate of 2 ° C / minute, and a graph in which the horizontal axis was set to temperature (° C.) and the vertical axis was changed as mass was obtained. The intersection X of the tangent to the horizontal portion on the low temperature side and the tangent to the inflection point on the low temperature side in the obtained graph is taken as the decomposition temperature of the polymer H1. The results are shown in Table 1.

(5) Evaluation of dispersibility of the composition The composition obtained in the above (2) was visually observed, and the dispersibility of the inorganic particles in the composition was evaluated based on the following evaluation criteria. The results are shown in Table 1. ○: The dispersed state of the inorganic particles was uniform, and no precipitate was visually observed. X: The dispersion state of the inorganic particles was not uniform, and the precipitate was visually confirmed.

<Example 1> (1) Preparation of a polymer 450 parts of propylene glycol monomethyl ether acetate (PGMEA) was added to a flask equipped with a cooling tube and a stirrer, and nitrogen substitution was performed. While stirring at 70 ° C, 71 parts of methyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1-[2-(methacryloxy)ethyl succinate were added dropwise at the same temperature for 30 minutes. Ester (manufactured by Sigma-Aldrich Japan Co., Ltd.) 29 parts, 2,2'-azobis(2,4-dimethylvaleronitrile) (manufactured by Wako Pure Chemical Industries, Ltd.), 6 parts, pentaerythritol IV (3-MPF propionate) [PEMP] (manufactured by SC Organic Chemical Co., Ltd.) 6 parts and 450 parts of a mixed solution of PGMEA were subjected to polymerization at the same temperature for 2 hours. After slowly cooling the reaction solution to room temperature, it was added dropwise to ethanol, and the precipitate was collected by filtration, and dried by a vacuum dryer at 40 ° C to obtain a white powder of a polymer (dispersant). Hereinafter, this polymer is referred to as a polymer A1.

The polymer A1 has the following structural unit.

(2) Preparation of the composition A composition was obtained in the same manner as in Comparative Example 1, except that the polymer A1 obtained in the above (1) was used instead of the polymer H1.

(3) Measurement of Weight Average Molecular Weight Mw of Polymer, Evaluation of Heat Resistance of Polymer, and Evaluation of Dispersibility of Composition In the same manner as in Comparative Example 1, the polymer A1 and the above (2) were obtained. The composition was measured and evaluated. The results are shown in Table 1.

Further, the decomposition rate of the polymer A1 was measured. 30 mg of the powder of the polymer A1 obtained in the above (1) was weighed into an aluminum frying pan, using a thermogravimetric analyzer "TGDTA6200" (manufactured by Seiko Instruments Inc.) at a temperature elevation rate of 10 ° C / min under air flow. After heating from 50 ° C to 230 ° C, holding at 230 ° C for 30 minutes, and further maintaining the amount of mass reduction at 230 ° C for 30 minutes, based on the following formula: decomposition rate (%) = {mass reduction amount (mg) / The amount (mg)} × 100 in the aluminum frying pan was measured and the decomposition rate was calculated. The decomposition rate was 1.91%.

<Example 2> (1) Preparation of a polymer 450 parts of propylene glycol monomethyl ether acetate (PGMEA) was added to a flask equipped with a cooling tube and a stirrer, and nitrogen substitution was performed. While stirring at 70 ° C, 51 parts of methyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) and N-cyclohexylmethyleneimine (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise at the same temperature for 30 minutes. Parts, 1-[2-(methacryloxy)ethyl] succinate (manufactured by Sigma-Aldrich, Japan) 29 parts, 2,2'-azobis(2,4-dimethylpentyl) 6 parts of nitrile (manufactured by Wako Pure Chemical Co., Ltd.), a mixed solution of pentaerythritol tetrakis(3-mercaptopropionate) (PEMP) (manufactured by SC Organic Chemical Co., Ltd.) and 6 parts of PGMEA at the same temperature 2 Hour polymerization. After slowly cooling the reaction solution to room temperature, it was added dropwise to ethanol, and the precipitate was collected by filtration, and dried by a vacuum dryer at 40 ° C to obtain a white powder of a polymer (dispersant). Hereinafter, this polymer is referred to as a polymer A2.

The polymer A2 has the following structural unit.

(2) Preparation of the composition A composition was obtained in the same manner as in Comparative Example 1, except that the polymer A2 obtained in the above (1) was used instead of the polymer H1.

(3) Measurement of Weight Average Molecular Weight Mw of Polymer, Evaluation of Heat Resistance of Polymer, and Evaluation of Dispersibility of Composition The polymer A2 and the obtained in the above (2) were obtained in the same manner as in Comparative Example 1. The composition was measured and evaluated. The results are shown in Table 1. Further, the decomposition rate of the polymer A2 was measured in the same manner as in Example 1 and found to be 1.71%.

<Example 3> (1) Preparation of a polymer 450 parts of propylene glycol monomethyl ether acetate (PGMEA) was added to a flask equipped with a cooling tube and a stirrer, and nitrogen substitution was performed. While stirring at 70 ° C, 74 parts of methyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 6-m-butylene iminohexanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise at the same temperature for 30 minutes. , 2,2'-azobis(2,4-dimethylvaleronitrile) (manufactured by Wako Pure Chemical Industries, Ltd.) 6 parts, pentaerythritol tetrakis(3-mercaptopropionate) [PEMP] (SC Organic Chemicals Co., Ltd.) The company produced a mixed solution of 6 parts and 450 parts of PGMEA, and carried out polymerization at the same temperature for 2 hours. After slowly cooling the reaction solution to room temperature, it was added dropwise to ethanol, and the precipitate was collected by filtration, and dried by a vacuum dryer at 40 ° C to obtain a white powder of a polymer (dispersant). Hereinafter, this polymer is referred to as polymer A3.

The polymer A3 has the following structural unit.

(2) Preparation of the composition A composition was obtained in the same manner as in Comparative Example 1, except that the polymer A3 obtained in the above (1) was used instead of the polymer H1.

(3) Measurement of Weight Average Molecular Weight Mw of Polymer, Evaluation of Heat Resistance of Polymer, and Evaluation of Dispersibility of Composition The polymer A3 and the obtained in the above (2) were obtained in the same manner as in Comparative Example 1. The composition was measured and evaluated. The results are shown in Table 1. Further, the decomposition rate of the polymer A3 was measured in the same manner as in Example 1 and found to be 0.95%.

The ¹ H-NMR (nuclear magnetic resonance) data of the polymer A3 is shown below. ¹ H-NMR (CDCl ₃ , 400 MHz, TMS) δ (ppm): δ = 4.05 - 4.20 (br, NCH ₂ , 2H), 3.75-3.50 (br, CH ₃ , 3H), 3.35-3.30 (br, CH, 1H), 2.7-2.63 (br, 1H), 2.35-2.25 (t, CH ₂ C=O, 2H), 1.2-2.1 (br, CH ₂ and methacrylic polymer backbone (CH ₂ and methacryl) Polymer backbone)) ppm Calculate the basis of each structural unit based on the integral ratio of δ=3.75-3.50 (from methyl methacrylate) to δ=4.05-4.20 (from 6-maleimide hexanoic acid) The ratio was confirmed to obtain the same polymer as the addition ratio.

<Example 4> (1) Preparation of polymer A 450 part of propylene glycol monomethyl ether acetate (PGMEA) was added to a flask equipped with a cooling tube and a stirrer, and nitrogen substitution was performed. While stirring at 70 ° C, 74 parts of N-cyclohexylmethyleneimine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 6-maleimide hexanoic acid were added dropwise at the same temperature for 30 minutes. 26 parts, 2,2'-azobis(2,4-dimethylvaleronitrile) (manufactured by Wako Pure Chemical Industries, Ltd.), and pentaerythritol tetrakis(3-mercaptopropionate) [PEMP] manufactured by Tokyo Chemical Industry Co., Ltd. (manufactured by SC Organic Chemical Co., Ltd.) A mixed solution of 6 parts and 450 parts of PGMEA was subjected to polymerization at the same temperature for 2 hours. After slowly cooling the reaction solution to room temperature, it was added dropwise to ethanol, and the precipitate was collected by filtration, and dried by a vacuum dryer at 40 ° C to obtain a white powder of a polymer (dispersant). Hereinafter, this polymer is referred to as a polymer A4.

The polymer A4 has the following structural unit.

(2) Preparation of the composition A composition was obtained in the same manner as in Comparative Example 1, except that the polymer A4 obtained in the above (1) was used instead of the polymer H1.

(3) Measurement of Weight Average Molecular Weight Mw of Polymer, Evaluation of Heat Resistance of Polymer, and Evaluation of Dispersibility of Composition The polymer A4 and the obtained in the above (2) were obtained in the same manner as in Comparative Example 1. The composition was measured and evaluated. The results are shown in Table 1. Further, the decomposition rate of the polymer A4 was measured in the same manner as in Example 1 and found to be 0.12%.

The ¹ H-NMR data of the polymer A4 is shown below. ¹ H-NMR (CDCl ₃ , 400 MHz, TMS) δ (ppm): δ = 4.10 - 4.25 (br, NCH ₂ , 2H), 3.70-3.20 (br, NCH, 1H), 2.90-2.70 (br, CH , 2H), 2.40-2.10 (br, CH ₂ C=O, 2H), 2.35-2.25 (t, CH ₂ C=O, 2H), 2.20-1.00 (br, CH ₂ ) ppm according to δ=4.10-4.25 The ratio of each structural unit was calculated from the integral ratio of δ = 2.90 to 2.70 (derived from the common main chain skeleton), and it was confirmed that the same polymer as the addition ratio was obtained. .

<Example 5> (1) Preparation of a composition Titanium oxide particles (TiO ₂ particles, manufactured by CIK NanoTek Co., Ltd.), 9 parts, and 1 part of (1) of Example 1 were placed in a glass bottle. 90 parts of the obtained polymer A1 and propylene glycol monomethyl ether acetate (PGMEA) were shaken by a bead mill for 8 hours, thereby obtaining a composition.

(2) Evaluation of Dispersibility of Composition The composition obtained in the above (1) was evaluated for dispersibility in the same manner as in Comparative Example 1. The results are shown in Table 1.

<Example 6> (1) Preparation of a composition 7.5 parts of hollow cerium oxide particles (hollow SiO ₂ particles, manufactured by Nippon Steel Mining Co., Ltd.) and 2.5 parts of (1) of Example 1 were placed in a glass bottle. 90 parts of the polymer A1 and propylene glycol monomethyl ether acetate (PGMEA) obtained in the above were shaken by a bead mill for 8 hours to obtain a composition.

(2) Evaluation of Dispersibility of Composition The composition obtained in the above (1) was evaluated for dispersibility in the same manner as in Comparative Example 1. The results are shown in Table 1.

<Example 7> (1) Preparation of a composition 9 parts of calcium carbonate particles (CaCO ₃ particles, manufactured by Shiraishi Chemical Industry Co., Ltd.) and 1 part of the polymerization obtained in (1) of Example 1 were placed in a glass bottle. 90 parts of the body A1 and propylene glycol monomethyl ether acetate (PGMEA) were shaken by a bead mill for 8 hours to obtain a composition.

(2) Evaluation of Dispersibility of Composition The composition obtained in the above (1) was evaluated for dispersibility in the same manner as in Comparative Example 1. The results are shown in Table 1.

[Table 1]

X‧‧‧ intersection of the tangent of the horizontal portion on the low temperature side and the tangent to the inflection point on the low temperature side

FIG. 1 is a schematic view showing an example of a graph obtained by using a thermogravimetric analyzer.

Claims (5)

A composition comprising: a polymer having a structural unit (i-1) derived from a polymerizable carboxylic acid compound having an ethylenically unsaturated bond and a bond via a linking group a carboxyl group bonded to the ethylenically unsaturated bond; and an inorganic particle. The composition according to claim 1, wherein the polymerizable carboxylic acid compound has an N-substituted maleimide structure. The composition according to claim 1 or 2, wherein the polymer further has a structural unit (i-2) derived from an N-substituted maleimide compound having no carboxyl group. The composition of claim 3, wherein the inorganic particles comprise semiconductor quantum dots. A polymer having a structural unit (i-1) derived from a polymerizable carboxylic acid compound having an ethylenically unsaturated bond and bonded to the ethylenically unsaturated bond via a linking group The carboxyl group and the polymerizable carboxylic acid compound have an N-substituted maleimide structure, and the acid value is 20 mgKOH/g or more and 150 mgKOH/g or less.