Curable composition

Abstract

The purpose of the present invention is to provide a curable composition containing semiconductor particles, said composition being capable of suppressing a decrease in the residual film ratio of a cured product when cured at a low temperature. The present invention is a curable composition containing semiconductor particles (A) and a resin (C), wherein the value X calculated using formula (1) from the acid value and the weight-average molecular weight Mw of the resin (C) is 10 to 59.75, and the double bond equivalent of the resin (C) is at least 100 g / eq but less than 600 g / eq.　Formula (1): X=[acid value (mg-KOH / g)×weight-average molecular weight Mw] / 10,000

Description

curable composition

[0001] The present invention relates to a curable composition comprising semiconductor particles.

[0002] Patent Document 1 describes that a curable composition containing quantum dots (A) and a photopolymerizable compound (B) is subjected to a drying step (pre-baking) at 100°C for 3 minutes to form a film, and then an exposure step is carried out by irradiating the film with light, and after development, a thermal curing step is carried out by carrying out a thermal curing treatment (post-baking) at 180°C for 1 hour to obtain a cured film.

[0003] Japanese Patent Application Laid-Open No. 2022-170673

[0004] A curable composition containing semiconductor particles such as quantum dots is preferably cured at a low temperature because this reduces energy costs. The inventors have found that when the curable composition is cured at a low temperature, the residual film rate after development of the cured film may be poor.

[0005] Therefore, an object of the present invention is to provide a curable composition containing semiconductor particles, which is capable of suppressing a decrease in the development residual film rate of the cured product when cured at low temperatures.

[0006] The present invention achieves the above-mentioned object as follows: [1] A curable composition comprising semiconductor particles (A) and a resin (C), wherein the value X calculated from the acid value and weight-average molecular weight Mw of the resin (C) using the following formula (1) is 10 or more and 59.75 or less, and the double bond equivalent of the resin (C) is 100 g / eq or more and less than 600 g / eq: X = {acid value (mg-KOH / g) × weight-average molecular weight Mw} / 10,000 ... (1) [2] The curable composition according to [1], wherein the acid value of the resin (C) is less than 85 mg-KOH / g. [3] The curable composition according to [1] or [2], wherein the weight-average molecular weight Mw of the resin (C) is 5,000 or more. [4] The curable composition according to any one of [1] to [3], wherein the mass ratio (A / C) of the semiconductor particles (A) to the resin (C) is 0.65 or more. [5] The curable composition according to any one of [1] to [4], further comprising a polymerizable compound (D), wherein the mass ratio (C / D) of the resin (C) to the polymerizable compound (D) is 2 or more. [6] The curable composition according to any one of [1] to [5], further comprising a polymerizable compound (D), wherein the polymerizable compound (D) comprises a polymerizable compound having one or more cyclic hydrocarbon groups and two ethylenically unsaturated bonds in one molecule. [7] The curable composition according to [6], wherein the polymerizable compound (D) further comprises a polymerizable compound having an acidic functional group and three or more ethylenically unsaturated bonds in one molecule. [8] The curable composition according to any one of [1] to [7], further comprising a light scattering agent (B).

[0007] According to the present invention, it is possible to suppress a decrease in the residual film rate after development of a cured product obtained by curing a curable composition containing semiconductor particles at a low temperature.

[0008] <<Curable Composition>> The curable composition preferably contains, in addition to the semiconductor particles (A) and the resin (C), at least one selected from the group consisting of an organic ligand (G), a light scattering agent (B), a polymerizable compound (D), a polymerization initiator (E), a light stabilizer (F), a leveling agent (H), and a solvent (J), as needed.

[0009] In this specification, the compounds exemplified as each component can be used alone or in combination of two or more, unless otherwise specified. When multiple types of each component are used, the content can be adjusted based on the total amount of the multiple types, unless otherwise specified.

[0010] <Semiconductor Particles (A)> The semiconductor particles (A) are preferably luminescent inorganic semiconductor particles that absorb primary light and emit light of a wavelength different from that of the primary light, and the luminescent inorganic semiconductor particles more preferably absorb primary light and emit green or red light, and further preferably convert the wavelength of blue light, which is the primary light, to the wavelength of red light or the wavelength of green light.

[0011] In this specification, "blue" refers to all light that is visually perceived as blue (all light having intensity in the blue wavelength range, for example, 380 nm to 495 nm), and is not limited to light of a single wavelength. "Green" refers to all light that is visually perceived as green (all light having intensity in the green wavelength range, for example, 495 nm to 585 nm), and is not limited to light of a single wavelength. "Red" refers to all light that is visually perceived as red (all light having intensity in the red wavelength range, for example, 585 nm to 780 nm), and is not limited to light of a single wavelength.

[0012] Examples of the semiconductor particles (A) include quantum dots and particles composed of a compound having a perovskite crystal structure (hereinafter also referred to as a "perovskite compound"), with quantum dots being preferred. Quantum dots are luminescent inorganic semiconductor fine particles having a particle diameter of 1 nm to 100 nm, which utilize the band gap of the semiconductor to absorb and emit ultraviolet light or visible light (e.g., blue light).

[0013] Examples of quantum dots include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, CdHgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZn Examples of the compound include compounds of Group 12 elements and Group 16 elements such as SeTe and HgZnSTe; compounds of Group 13 elements and Group 15 elements such as GaN, GaP, GaAs, AlN, AlP, AlAs, InN, InP, InAs, GaNP, GaNAs, GaPAs, AlNP, AlNAs, AlPAs, InNP, InNAs, InPAs, GaAlNP, GaAlNAs, GaAlPAs, GaInNP, GaInNAs, GaInPAs, InAlNP, InAlNAs, and InAlPAs; and compounds of Group 14 elements and Group 16 elements such as PdS and PbSe.

[0014] When the quantum dots contain S or Se, the quantum dots may be surface-modified with a metal oxide or an organic substance. The use of surface-modified quantum dots can prevent S or Se from being extracted by a reactive component that is or may be contained in the curable composition.

[0015] The quantum dots may also have a core-shell structure formed by combining the above compounds, such as particles having a CdSe core and a ZnS shell, or particles having an InP core and a ZnSeS shell.

[0016] Since the energy state of quantum dots depends on their size, it is possible to freely select the emission wavelength by changing the particle diameter. Furthermore, the narrow spectral width of the light emitted from quantum dots is advantageous for widening the color gamut of display devices. Furthermore, quantum dots have high responsiveness, which is advantageous in terms of the utilization efficiency of primary light.

[0017] The perovskite compound is a compound having a perovskite-type crystal structure and containing A, B, and X as components.

[0018] A is a component located at each vertex of a hexahedron with B at the center in the perovskite crystal structure, and is a monovalent cation.

[0019] X represents a component located at each vertex of an octahedron with B at the center in the perovskite crystal structure, and is at least one ion selected from the group consisting of halide ions and thiocyanate ions.

[0020] B is a component located at the center of a hexahedron with A as a vertex and an octahedron with X as a vertex in the perovskite crystal structure, and is a metal ion.

[0021] The perovskite compound containing A, B, and X as components is not particularly limited, and may be a compound having any of a three-dimensional structure, a two-dimensional structure, and a pseudo-two-dimensional structure.

[0022] In the case of a three-dimensional structure, the perovskite compound is ABX （３＋δ） It is expressed as:

[0023] In the case of a two-dimensional structure, the perovskite compound is ２ BX （４＋δ） It is expressed as:

[0024] Here, δ is a number that can be appropriately changed depending on the charge balance of B, and is between −0.7 and 0.7.

[0025] A perovskite compound, ABX （３＋δ） Preferred specific examples of the compound having a three-dimensional perovskite-type crystal structure represented by the formula: ３ NH ３ PbBr ３ , C.H. ３ NH ３ PbCl ３ , C.H. ３ NH ３ PbI ３ , C.H. ３ NH ３ PbBr （３－ｙ） I ｙ(0<y<3)、CH ３ NH ３ PbBr （３－ｙ） Cl ｙ (0<y<3)、(H ２ N=CH-NH ２ )PbBr ３ 、(H ２ N=CH-NH ２ )PbCl ３ 、(H ２ N=CH-NH ２ )PbI ３ 、 CH ３ NH ３ Pb （１－ａ） Ca ａ Br ３ (0<a≦0.7)、CH ３ NH ３ Pb （１－ａ） Sr ａ Br ３ (0<a≦0.7)、CH ３ NH ３ Pb （１－ａ） La ａ Br （３＋δ） (0<a≦0.7,0<δ≦0.7)、CH ３ NH ３ Pb （１－ａ） Ba ａ Br ３ (0<a≦0.7)、CH ３ NH ３ Pb （１－ａ） Dy ａ Br （３＋δ） (0<a≦0.7,0<δ≦0.7)、 CH ３ NH ３ Pb （１－ａ） Na ａ Br （３＋δ） (0<a≦0.7,-0.7≦δ<0)、CH ３ NH ３ Pb （１－ａ） Li ａ Br （３＋δ） (0<a≦0.7,-0.7≦δ<0)、 CsPb （１－ａ） Na ａ Br （３＋δ） (0<a≦0.7,-0.7≦δ<0)、CsPb （１－ａ） Li ａ Br （３＋δ）(0<a≦0.7,-0.7≦δ<0)、 CH ３ NH ３ Pb （１－ａ） Na ａ Br （３＋δ－ｙ） I ｙ (0<a≦0.7,-0. 7≦δ<0,0<y<3)、CH ３ NH ３ Pb （１－ａ） Li ａ Br （３＋δ－ｙ） I ｙ (0<a≦0.7,-0.7≦δ<0,0<y<3)、CH ３ NH ３ Pb （１－ａ） Na ａ Br （３＋δ－ｙ） Cl ｙ (0<a≦0.7,-0.7≦δ<0,0<y<3)、CH ３ NH ３ Pb （１－ａ） Li ａ Br （３＋δ－ｙ） Cl ｙ (0<a≦0.7,-0.7≦δ<0,0<y<3)、 (H ２ N=CH-NH ２ )Pb （１－ａ） Na ａ Br （３＋δ） (0<a≦0.7,-0.7≦δ<0)、(H ２ N=CH-NH ２ )Pb （１－ａ） Li ａ Br （３＋δ） (0<a≦0.7,-0.7≦δ<0)、(H ２ N=CH-NH ２ )Pb （１－ａ） Na ａ Br （３＋δ－ｙ） I ｙ (0<a≦0.7,-0.7≦δ<0,0<y<3)、(H ２ N=CH-NH ２ )Pb （１－ａ） Na ａ Br （３＋δ－ｙ） Cl ｙ (0<a≦0.7,-0.7≦δ<0,0<y<3)、 CsPbBr ３ 、CsPbCl ３ 、CsPbI ３ 、CsPbBr （３－ｙ）I ｙ (0<y<3)、CsPbBr （３－ｙ） Cl ｙ (0<y<3)、CH ３ NH ３ PbBr （３－ｙ） Cl ｙ (0<y<3)、 CH ３ NH ３ Pb （１－ａ） Zn ａ Br ３ (0<a≦0.7)、CH ３ NH ３ Pb （１－ａ） Al ａ Br （３＋δ） (0<a≦0.7,0≦δ≦0.7)、CH ３ NH ３ Pb （１－ａ） Co ａ Br ３ (0<a≦0.7)、CH ３ NH ３ Pb （１－ａ） Mn ａ Br ３ (0<a≦0.7)、CH ３ NH ３ Pb （１－ａ） Mg ａ Br ３ (0<a≦0.7)、 CsPb （１－ａ） Zn ａ Br ３ (0<a≦0.7)、CsPb （１－ａ） Al ａ Br （３＋δ） (0<a≦0.7,0<δ≦0.7)、CsPb （１－ａ） Co ａ Br ３ (0<a≦0.7)、CsPb （１－ａ） Mn ａ Br ３ (0<a≦0.7)、CsPb （１－ａ） Mg ａ Br ３ (0<a≦0.7)、 CH ３ NH ３ Pb （１－ａ） Zn ａ Br （３－ｙ） I ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３Pb （１－ａ） Al ａ Br （３＋δ－ｙ） I ｙ (0<a≦0.7,0<δ≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Co ａ Br （３－ｙ） I ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Mn ａ Br （３－ｙ） I ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Mg ａ Br （３－ｙ） I ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Zn ａ Br （３－ｙ） Cl ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Al ａ Br （３＋δ－ｙ） Cl ｙ (0<a≦0.7,0<δ≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Co ａ Br （３＋δ－ｙ） Cl ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Mn ａ Br （３－ｙ） Cl ｙ (0<a≦0.7,0<y<3)、CH ３ NH ３ Pb （１－ａ） Mg ａ Br （３－ｙ） Cl ｙ (0<a≦0.7,0<y<3)、 (H ２ N=CH-NH ２ )Zn ａ Br３ (0<a≦0.7), (H ２ N=CH-NH ２ ) Mg ａ Br ３ (0<a≦0.7), (H ２ N=CH-NH ２ ) Pb （１－ａ） Zn ａ Br （３－ｙ） I ｙ (0<a≦0.7, 0<y<3), (H ２ N=CH-NH ２ ) Pb （１－ａ） Zn ａ Br （３－ｙ） Cl ｙ (0<a≦0.7, 0<y<3), etc.

[0026] A perovskite compound, ２ BX （４＋δ） Preferable specific examples of the compound having a two-dimensional perovskite-type crystal structure represented by the formula (C ４ H ９ NH ３ ) ２ PbBr ４ , (C ４ H ９ NH ３ ) ２ PbCl ４ , (C ４ H ９ NH ３ ) ２ PbI ４ , (C ７ H １５ NH ３ ) ２ PbBr ４ , (C ７ H １５ NH ３ ) ２ PbCl ４ , (C ７ H １５ NH ３ ) ２ PbI ４ , (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Li ａ Br （４＋δ）(0<a≦0.7,-0.7≦δ<0)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Na ａ Br （４＋δ） (0<a≦0.7,-0.7≦δ<0)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Rb ａ Br （４＋δ） (0<a≦0.7,-0.7≦δ<0)、 (C ７ H １５ NH ３ ) ２ Pb （１－ａ） Na ａ Br （４＋δ） (0<a≦0.7,-0.7≦δ<0)、(C ７ H １５ NH ３ ) ２ Pb （１－ａ） Li ａ Br （４＋δ） (0<a≦0.7,-0.7≦δ<0)、(C ７ H １５ NH ３ ) ２ Pb （１－ａ） RbaBr （４＋δ） (0<a≦0.7,-0.7≦δ<0)、 (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Na ａ Br （４＋δ－ｙ） I ｙ (0<a≦0.7,-0.7≦δ<0,0<y<4)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Li ａ Br （４＋δ－ｙ） I ｙ (0<a≦0.7,-0.7≦δ<0,0<y<4)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Rb ａ Br（４＋δ－ｙ） I ｙ (0<a≦0.7,-0.7≦δ<0,0<y<4)、 (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Na ａ Br （４＋δ－ｙ） Cl ｙ (0<a≦0.7,-0.7≦δ<0,0<y<4)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Li ａ Br （４＋δ－ｙ） Cl ｙ (0<a≦0.7,-0.7≦δ<0,0<y<4)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Rb ａ Br （４＋δ－ｙ） Cl ｙ (0<a≦0.7,-0.7≦δ<0,0<y<4)、 (C ４ H ９ NH ３ ) ２ PbBr ４ 、(C ７ H １５ NH ３ ) ２ PbBr ４ 、 (C ４ H ９ NH ３ ) ２ PbBr （４－ｙ） Cl ｙ (0<y<4)、(C ４ H ９ NH ３ ) ２ PbBr （４－ｙ） I ｙ (0<y<4)、 (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Zn ａ Br ４ (0<a≦0.7)、(C ４ H ９ NH ３ )２ Pb （１－ａ） Mg ａ Br ４ (0<a≦0.7)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Co ａ Br ４ (0<a≦0.7)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Mn ａ Br ４ (0<a≦0.7)、 (C ７ H １５ NH ３ ) ２ Pb （１－ａ） Zn ａ Br ４ (0<a≦0.7)、(C ７ H １５ NH ３ ) ２ Pb （１－ａ） Mg ａ Br ４ (0<a≦0.7)、(C ７ H １５ NH ３ ) ２ Pb （１－ａ） Co ａ Br ４ (0<a≦0.7)、(C ７ H １５ NH ３ ) ２ Pb （１－ａ） Mn ａ Br ４ (0<a≦0.7)、 (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Zn ａ Br （４－ｙ） I ｙ (0<a≦0.7,0<y<4)、(C ４ H ９ NH ３ ) ２ Pb （１－ａ） Mg ａ Br （４－ｙ） I ｙ(0<a≦0.7, 0<y<4), (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Co ａ Br （４－ｙ） I ｙ (0<a≦0.7, 0<y<4), (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Mn ａ Br （４－ｙ） I ｙ (0<a≦0.7, 0<y<4), (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Zn ａ Br （４－ｙ） Cl ｙ (0<a≦0.7, 0<y<4), (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Mg ａ Br （４－ｙ） Cl ｙ (0<a≦0.7, 0<y<4), (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Co ａ Br （４－ｙ） Cl ｙ (0<a≦0.7, 0<y<4), (C ４ H ９ NH ３ ) ２ Pb （１－ａ） Mn ａ Br （４－ｙ） Cl ｙ (0<a≦0.7, 0<y<4), etc.

[0027] The content of the semiconductor particles (A) in the curable composition is preferably 3% by mass or more and 60% by mass or less, more preferably 10% by mass or more and 55% by mass or less, still more preferably 20% by mass or more and 50% by mass or less, and particularly preferably 30% by mass or more and 50% by mass or less, relative to 100% by mass of the solid content of the curable composition.

[0028] In this specification, the total amount of solids in the curable composition means the sum of all components contained in the curable composition excluding the solvent (J). The content of each component in the solids of the curable composition can be measured by known analytical means such as liquid chromatography or gas chromatography. The content of each component in the solids of the curable composition may be calculated from the blending during preparation of the curable composition.

[0029] <Organic Ligand (G)> The semiconductor particles (A) may be present in the curable composition in a state where an organic ligand (G) is coordinated thereto. The organic ligand (G) is, for example, an organic compound having a polar group that exhibits coordination ability with the semiconductor particles (A). The organic ligand (G) can be coordinated to, for example, the surface of the semiconductor particles (A). The curable composition may contain one or more types of organic ligands (G).

[0030] It is preferable that at least a portion of the molecules of the organic ligand (G) are coordinated to the semiconductor particles (A), and all or almost all of the molecules may be coordinated to the semiconductor particles (A). The inclusion of the organic ligand (G) coordinated to the semiconductor particles (A) can be advantageous from the viewpoints of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer.

[0031] The polar group of the organic ligand (G) may be, for example, a thiol group (—SH), a carboxyl group (—COOH), or an amino group (—NH ２ ) is at least one group selected from the group consisting of. A polar group selected from this group can be advantageous in improving coordination with the semiconductor particles (A). High coordination can contribute to improving the stability and dispersibility of the semiconductor particles (A) in the curable composition, as well as improving the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer. Among these, it is more preferable that the polar group is at least one group selected from the group consisting of a thiol group and a carboxy group. The organic ligand (G) can have one or more polar groups.

[0032] The organic ligand (G) is, for example, a ligand represented by the following formula (x): Ａ -R Ｘ(x) wherein X Ａ is the polar group described above, and R Ｘ is a monovalent hydrocarbon group which may contain a heteroatom (N, O, S, halogen atom, etc.). The hydrocarbon group may have one or more unsaturated bonds such as a carbon-carbon double bond. The hydrocarbon group may have a linear, branched, or cyclic structure. The number of carbon atoms in the hydrocarbon group is, for example, 1 to 40, or may be 1 to 30. A methylene group contained in the hydrocarbon group may be substituted with -O-, -S-, -C(=O)-, -C(=O)-O-, -O-C(=O)-, -C(=O)-NH-, -NH-, etc.

[0033] group R Ｘ may contain a polar group. Specific examples of the polar group include the polar group X Ａ Reference is made to the above description of

[0034] polar group Ａ Specific examples of organic ligands having a carboxy group as the carboxyl group include formic acid, acetic acid, and propionic acid, as well as saturated or unsaturated fatty acids. Specific examples of saturated or unsaturated fatty acids include saturated fatty acids such as butyric acid, pentanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, and lignoceric acid; monounsaturated fatty acids such as myristoleic acid, palmitoleic acid, oleic acid, icosenoic acid, erucic acid, and nervonic acid; and polyunsaturated fatty acids such as linoleic acid, α-linolenic acid, γ-linolenic acid, stearic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosatetraenoic acid, docosadienoic acid, and adrenic acid (docosatetraenoic acid).

[0035] polar group Ａ Specific examples of organic ligands having a thiol group or an amino group as the polar group X Ａ The organic ligand includes an organic ligand in which the carboxy group of an organic ligand having a carboxy group as the carboxyl group is replaced with a thiol group or an amino group.

[0036] In addition to the above, examples of the organic ligand represented by the formula (x) include the compound (G-1) and the compound (G-2).

[0037] [Compound (G-1)] The compound (G-1) is a compound having a first functional group and a second functional group. The first functional group is a carboxy group (-COOH), and the second functional group is a carboxy group or a thiol group (-SH). Since the compound (G-1) has a carboxy group and / or a thiol group, it can serve as a ligand that coordinates to the semiconductor particles (A). The curable composition may contain only one type of compound (G-1), or may contain two or more types of compound (G-1).

[0038] An example of the compound (G-1) is a compound represented by the following formula (G-1a): The compound (G-1) may be an acid anhydride of the compound represented by the formula (G-1a).

[0039]

[0040] [In the formula, R Ｂ represents a divalent hydrocarbon group. Ｂ When —CH is present, they may be the same or different. The hydrocarbon group may have one or more substituents. When a plurality of substituents is present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. —CH contained in the hydrocarbon group ２ - is -O-, -S-, -SO ２ may be substituted with at least one of -, -CO-, and -NH-, and p represents an integer of 1 to 10.

[0041] R Ｂ Examples of the divalent hydrocarbon group represented by the formula (I) include a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups.

[0042] Examples of the chain hydrocarbon group include a linear or branched alkanediyl group, the number of carbon atoms of which is usually 1 to 50, preferably 1 to 20, and more preferably 1 to 10. Examples of the alicyclic hydrocarbon group include a monocyclic or polycyclic cycloalkanediyl group, the number of carbon atoms of which is usually 3 to 50, preferably 3 to 20, and more preferably 3 to 10. Examples of the aromatic hydrocarbon group include a monocyclic or polycyclic arenediyl group, the number of carbon atoms of which is usually 6 to 20.

[0043] Examples of the substituent that the hydrocarbon group may have include an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms, a carboxy group, an amino group, a halogen atom, etc. The substituent that the hydrocarbon group may have is preferably a carboxy group, an amino group, or a halogen atom.

[0044] The —CH contained in the hydrocarbon group ２ When - is replaced with at least one of -O-, -CO- and -NH-, -CH ２ The group which is replaced by - is preferably at least one of -CO- and -NH-, more preferably -NH-. p is preferably 1 or 2.

[0045] Examples of the compound represented by formula (G-1a) include compounds represented by the following formulas (1-1) to (1-9).

[0046]

[0047] Specific examples of the compound represented by formula (G-1a) by chemical name include mercaptoacetic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutanoic acid, 4-mercaptobutanoic acid, mercaptosuccinic acid, mercaptostearic acid, mercaptooctanoic acid, 4-mercaptobenzoic acid, 2,3,5,6-tetrafluoro-4-mercaptobenzoic acid, L-cysteine, N-acetyl-L-cysteine, 3-methoxybutyl 3-mercaptopropionate, and 3-mercapto-2-methylpropionic acid. Of these, 3-mercaptopropionic acid and mercaptosuccinic acid are preferred.

[0048] Another example of the compound (G-1) is a polycarboxylic acid compound, and preferably includes a compound (G-1b) in which —SH in the compound represented by the above formula (G-1a) is replaced with a carboxy group (—COOH).

[0049] Examples of the compound (G-1b) include the following compounds:

[0050] Succinic acid, glutaric acid, adipic acid, octafluoroadipic acid, azelaic acid, dodecanedioic acid, tetradecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, dodecafluorosuberic acid, 3-ethyl-3-methylglutaric acid, hexafluoroglutaric acid, trans-3-hexenedioic acid, sebacic acid, hexadecafluorosebacic acid, acetylenedicarboxylic acid, trans-aconitic acid, 1,3-adamantanedicarboxylic acid, bicyclo[2.2.2]octane-1,4-dicarboxylic acid, cis-4-cis- Cyclohexene-1,2-dicarboxylic acid, 1,1-cyclopropanedicarboxylic acid, 1,1-cyclobutanedicarboxylic acid, cis- or trans-1,3-cyclohexanedicarboxylic acid, cis- or trans-1,4-cyclohexanedicarboxylic acid, 1,1-cyclopentanediacetic acid, 1,2,3,4-cyclopentanetetracarboxylic acid, decahydro-1,4-naphthalenedicarboxylic acid, 2,3-norbornanedicarboxylic acid, 5-norbornene-2,3-dicarboxylic acid, phthalic acid, 3-fluorophthalic acid, isophthalic acid, tetrafluoroisophthalic acid Phthalic acid, terephthalic acid, tetrafluoroterephthalic acid, 2,5-dimethylterephthalic acid, 2,6-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,1'-ferrocenedicarboxylic acid, 2,2'-biphenyldicarboxylic acid, 4,4'-biphenyldicarboxylic acid, 2,5-furandicarboxylic acid, benzophenone-2,4'-dicarboxylic acid monohydrate, benzophenone-4,4'-dicarboxylic acid, 2,3-pyrazinedicarboxylic acid, 2,3-pyridinedicarboxylic acid, 2,4-pyridinedicarboxylic acid, 3,5-pyridinedicarboxylic acid, 2,5-pyridinedicarboxylic acid, 2,6-pyridinedicarboxylic acid, 3,4-pyridinedicarboxylic acid, pyrazole-3,5-dicarboxylic acid monohydrate, 4,4'-stilbenedicarboxylic acid, anthraquinone-2,3-dicarboxylic acid, 4-(carboxymethyl)benzoic acid, chelidonic acid monohydrate, azobenzene-4,4'-dicarboxylic acid, azobenzene-3,3'-dicarboxylic acid, chlorendic acid, 1H-imidazole-4,5-dicarboxylic acid, 2,2-bis(4-carboxyphenyl)hexafluoropropane, 1,10-bis(4-carboxyphenoxy)decane, dipropylmalonic acid, dithiodiglycolic acid, 3,3'-dithiodipropionic acid, 4,4'-dithiodibutanoic acid, 4,4'-dicarboxydiphenyl ether, 4,4'-dicarboxydiphenyl sulfone, ethylene glycol bis(4-carboxyphenyl)ether, 3,4-ethylenedioxythiophene-2,5-dicarboxylic acid, 4,4'-isopropylidenediphenoxyacetic acid, 1,3-acetonedicarboxylic acid, methylenedisalicylic acid, 5,5'-thiodisalicylic acid, tris(2-carboxyethyl)isocyanurate, tetrafluorosuccinic acid, α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid, 1,3,5-benzenetricarboxylic acid, etc.

[0051] From the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer, the molecular weight of the compound (G-1) is preferably 3,000 or less, more preferably 2,500 or less, even more preferably 2,000 or less, still more preferably 1,000 or less, particularly preferably 800 or less, and most preferably 500 or less. The molecular weight of the compound (G-1) is usually 100 or more.

[0052] The molecular weight may be a number average molecular weight or a weight average molecular weight, where the number average molecular weight and the weight average molecular weight are the number average molecular weight and the weight average molecular weight, respectively, measured by gel permeation chromatography (GPC) in terms of standard polystyrene.

[0053] When the curable composition contains the compound (G-1), the content ratio of the compound (G-1) to the semiconductor particles (A) in the curable composition, in mass ratio, is preferably from 0.001 to 1, more preferably from 0.01 to 0.5, and even more preferably from 0.02 to 0.45. Having the content ratio within this range can be advantageous from the viewpoints of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when the cured film is used as a wavelength conversion layer.

[0054] When the curable composition contains the compound (G-1), from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when the cured film is used as a wavelength conversion layer, the content of the compound (G-1) in the curable composition is preferably from 0.1% by mass to 20% by mass, more preferably from 0.2% by mass to 20% by mass, even more preferably from 0.2% by mass to 10% by mass, still more preferably from 0.5% by mass to 10% by mass, and particularly preferably from 0.5% by mass to 8% by mass, relative to the total amount of the solids in the curable composition.

[0055] [Compound (G-2)] Compound (G-2) is a compound different from compound (G-1), which contains a polyalkylene glycol structure and has a polar group at a molecular end. The molecular end is preferably the end of the longest carbon chain in compound (G-2) (a carbon atom in the carbon chain may be replaced with another atom such as an oxygen atom).

[0056] The curable composition may contain only one type of compound (G-2), or may contain two or more types of compound (G-2). The curable composition may contain either compound (G-1) or compound (G-2), or may contain compound (G-1) and compound (G-2).

[0057] The compound containing a polyalkylene glycol structure and having the first and second functional groups is considered to belong to the compound (G-1).

[0058] The polyalkylene glycol structure is represented by the following formula:

[0059]

[0060] (n is an integer of 2 or more). Ｃ is an alkylene group, for example, an ethylene group, a propylene group, etc.

[0061] A specific example of the compound (G-2) is a polyalkylene glycol compound represented by the following formula (G-2a):

[0062]

[0063] In formula (G-2a), X is a polar group, Y is a monovalent group, and Z Ｃ is a divalent or trivalent group. n is an integer of 2 or more. m is 1 or 2. R Ｃ is an alkylene group.

[0064] The polar group X is a thiol group (-SH), a carboxyl group (-COOH), and an amino group (-NH ２ ) is preferably at least one group selected from the group consisting of. A polar group selected from this group can be advantageous in terms of enhancing coordination with the semiconductor particles (A). Among these, from the viewpoints of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer, it is more preferable that the polar group X is at least one group selected from the group consisting of a thiol group and a carboxy group.

[0065] The group Y is a monovalent group. The group Y is not particularly limited, and examples thereof include monovalent hydrocarbon groups which may have a substituent (N, O, S, halogen atom, etc.). The —CH ２ The - may be substituted by -O-, -S-, -C(=O)-, -C(=O)-O-, -O-C(=O)-, -C(=O)-NH-, -NH-, etc. The number of carbon atoms in the hydrocarbon group is, for example, 1 or more and 12 or less. The hydrocarbon group may have an unsaturated bond.

[0066] Examples of the group Y include alkyl groups having a linear, branched, or cyclic structure and having 1 to 12 carbon atoms; and alkoxy groups having a linear, branched, or cyclic structure and having 1 to 12 carbon atoms. The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 8, more preferably 1 to 6, and even more preferably 1 to 4. The —CH ２ - may be substituted by -O-, -S-, -C(=O)-, -C(=O)-O-, -O-C(=O)-, -C(=O)-NH-, -NH-, etc. Among these, the group Y is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms, and more preferably a linear alkoxy group having 1 to 4 carbon atoms.

[0067] The group Y may contain a polar group. Examples of the polar group include a thiol group (—SH), a carboxyl group (—COOH), and an amino group (—NH ２ ) is at least one group selected from the group consisting of: As described above, however, a compound containing a polyalkylene glycol structure and having the first functional group and the second functional group is considered to belong to the compound (G-1). The polar group is preferably located at the terminal of the group Y.

[0068] Base Z Ｃ is a divalent or trivalent group. Ｃ is not particularly limited, and examples thereof include divalent or trivalent hydrocarbon groups which may contain heteroatoms (such as N, O, S, and halogen atoms). The number of carbon atoms in the hydrocarbon group is, for example, 1 to 24. The hydrocarbon group may have an unsaturated bond.

[0069] A divalent group Z Ｃ Examples of the alkyl group include alkylene groups having a linear, branched, or cyclic structure and having 1 to 24 carbon atoms; and alkenylene groups having a linear, branched, or cyclic structure and having 1 to 24 carbon atoms. The number of carbon atoms in the alkyl group and alkenylene group is preferably 1 to 12, more preferably 1 to 8, and even more preferably 1 to 4. The —CH group contained in the alkyl group and alkenylene group is ２ - may be substituted by -O-, -S-, -C(=O)-, -C(=O)-O-, -O-C(=O)-, -C(=O)-NH-, -NH-, etc. Ｃ Examples of the divalent group include the group Z Ｃ Examples of such groups include groups obtained by removing one hydrogen atom from the above.

[0070] Base Z Ｃ may have a branched structure. Ｃ may have a polyalkylene glycol structure other than the polyalkylene glycol structure represented by the formula (G-2a) in a branched chain other than the branched chain containing the polyalkylene glycol structure represented by the formula (G-2a) above.

[0071] Among them, the base ZＣ is preferably a linear or branched alkylene group having 1 to 6 carbon atoms, and more preferably a linear alkylene group having 1 to 4 carbon atoms.

[0072] R Ｃ is an alkylene group, preferably a linear or branched alkylene group having 1 to 6 carbon atoms, and more preferably a linear alkylene group having 1 to 4 carbon atoms.

[0073] In formula (G-2a), n is an integer of 2 or more, preferably 2 or more and 540 or less, more preferably 2 or more and 120 or less, and even more preferably 2 or more and 60 or less.

[0074] The molecular weight of compound (G-2) may be, for example, about 150 or more and 10,000 or less. From the viewpoints of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer, the molecular weight is preferably 150 or more and 5,000 or less, and more preferably 150 or more and 4,000 or less. The molecular weight may be a number average molecular weight or a weight average molecular weight. In this case, the number average molecular weight and the weight average molecular weight are, respectively, number average molecular weight and weight average molecular weight in terms of standard polystyrene measured by GPC.

[0075] When the curable composition contains the compound (G-2), the content ratio of the compound (G-2) to the semiconductor particles (A) in the curable composition, in mass ratio, is preferably from 0.001 to 2, more preferably from 0.01 to 1.5, and even more preferably from 0.1 to 1. Having the content ratio within this range can be advantageous from the viewpoints of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer.

[0076] When the curable composition contains the compound (G-2), from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer, the content of the compound (G-2) in the curable composition is preferably from 0.1% by mass to 40% by mass, more preferably from 0.1% by mass to 20% by mass, even more preferably from 1% by mass to 15% by mass, and still more preferably from 2% by mass to 12% by mass, relative to the total amount of the solids of the curable composition.

[0077] When the curable composition contains an organic ligand (G), the ratio of the content of the organic ligand (G) to the semiconductor particles (A) in the curable composition is, in mass ratio, preferably 0.001 to 1, more preferably 0.01 to 0.8, and even more preferably 0.02 to 0.5. When the content ratio is within this range, it can be advantageous from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer. The content of the organic ligand (G) here refers to the total content of all organic ligands contained in the curable composition.

[0078] From the viewpoints of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity when a cured film of the curable composition is used as a wavelength conversion layer, the total content of the semiconductor particles (A) and the organic ligand (G) in the curable composition is preferably 10% by mass or more and 75% by mass or less, and more preferably 12% by mass or more and 70% by mass or less, relative to the total amount of solids in the curable composition.

[0079] <Resin (C)> Examples of the resin (C) include the following resins [K1] to [K6].

[0080] Resin [K1]: a copolymer having a structural unit derived from at least one (a) (hereinafter also referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and a structural unit derived from a monomer (c) (different from (a)) (hereinafter also referred to as "(c)") copolymerizable with (a); Resin [K2]: a copolymer having a structural unit derived from (a), a structural unit derived from (c), and a structural unit derived from a monomer (b) (hereinafter also referred to as "(b)") having a cyclic ether structure and an ethylenically unsaturated bond having 2 to 4 carbon atoms; Resin [K3]: a copolymer having a structural unit obtained by adding (b) to the structural unit derived from (a), and a structural unit derived from (c); Resin [K4]: a copolymer having a structural unit obtained by adding (b) to the structural unit derived from (a), and further ester-bonding a carboxylic acid anhydride, and a structural unit derived from (c). Resin [K5]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and a structural unit derived from the (c); Resin [K6]: A copolymer having a structural unit obtained by adding the (a) to a structural unit derived from the (b) and further linking a carboxylic acid anhydride via an ester bond, and a structural unit derived from the (c).

[0081] Examples of (a) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Examples of suitable unsaturated dicarboxylic acid anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl]; and unsaturated (meth)acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)(meth)acrylic acid.

[0082] Among these, (meth)acrylic acid, mono[2-(meth)acryloyloxyethyl] succinate, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity, etc.

[0083] In this specification, (meth)acrylic acid means acrylic acid and / or methacrylic acid. The same applies to "(meth)acryloyl", "(meth)acrylate", etc.

[0084] (b) is, for example, a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0085] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0086] Examples of (b1) include a monomer (b1-1) (hereinafter may be referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter may be referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0087] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0088] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., CELLOXIDE 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER M100; manufactured by Daicel Corporation), compounds represented by formula (BI) and compounds represented by formula (BII).

[0089]

[0090] [In formula (BI) and formula (BII), R e and R f represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. e and X f is a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g represents —NH—. g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0091] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxyl group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl groups. R e and R fPreferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0092] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. e and X f Preferred examples of * include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0093] Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (BI-15). Among these, compounds represented by formula (BI-1), formula (BI-3), formula (BII-5), formula (BI-7), formula (BI-9), or formula (BI-11) to formula (BI-15) are preferred, and compounds represented by formula (BI-1), formula (BI-7), formula (BI-9), or formula (BI-15) are more preferred.

[0094]

[0095] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15). Among these, compounds represented by formula (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), or (BII-11) to (BII-15) are preferred, and compounds represented by formula (BII-1), (BII-7), (BII-9), or (BII-15) are more preferred.

[0096]

[0097] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.

[0098] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane.

[0099] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Ltd.) and tetrahydrofurfuryl methacrylate.

[0100] As (b), (b1) is preferred in that it can further increase reliability such as chemical resistance.

[0101] A monomer having an oxirane ring and an ethylenically unsaturated bond is preferred as (b) because it has high reactivity during the production of Resins [K3] to [K6] and is unlikely to leave unreacted (b).

[0102] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ２，６ ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes referred to as "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 ２，６](meth)acrylic acid esters such as decene-8-yl(meth)acrylate (commonly known as "dicyclopentenyl(meth)acrylate" in the technical field), dicyclopentanyloxyethyl(meth)acrylate, isobornyl(meth)acrylate, adamantyl(meth)acrylate, allyl(meth)acrylate, propargyl(meth)acrylate, phenyl(meth)acrylate, naphthyl(meth)acrylate, and benzyl(meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl(meth)acrylate and 2-hydroxypropyl(meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Cyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as 5-(2-(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene), 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene isoprene, and 2,3-dimethyl-1,3-butadiene.

[0103] Among the above, from the viewpoint of copolymerization reactivity, methyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and the like are preferred.

[0104] In the resin [K1], the proportions of the structural units derived from each of the structural units are preferably, of all the structural units constituting the resin [K1], structural units derived from (a): 2 mol% to 60 mol% and structural units derived from (c): 40 mol% to 98 mol%, and more preferably structural units derived from (a): 10 mol% to 50 mol% and structural units derived from (c): 50 mol% to 90 mol%.

[0105] When the ratio of the structural units of the resin [K1] is within the above range, the storage stability and solvent resistance tend to be excellent.

[0106] Resin [K1] can be produced, for example, by referring to the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the cited references described in said literature.

[0107] Specifically, a method may be mentioned in which predetermined amounts of (a) and (c), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example, by replacing oxygen with nitrogen, and the mixture is heated and kept warm while being stirred.

[0108] The polymerization initiator, solvent, etc. used are not particularly limited, and those commonly used in the relevant field can be used. For example, the polymerization initiator includes an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and an organic peroxide (benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, etc.), and the solvent may be any solvent that dissolves each monomer, such as the solvent (J) described below.

[0109] The obtained copolymer may be used as a solution after the reaction as it is, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) extracted by a method such as reprecipitation. If a solvent (J) described below is used as the solvent during polymerization, the solution after the reaction can be used as it is for preparing the composition, thereby simplifying the production process of the composition.

[0110] In the resin [K2], the proportions of the structural units derived from each of the above are preferably, of all the structural units constituting the resin [K2]: structural units derived from (a): 2 to 45 mol % structural units derived from (b): 2 to 95 mol % structural units derived from (c): 1 to 65 mol %, and more preferably, structural units derived from (a): 5 to 40 mol % structural units derived from (b): 5 to 80 mol % structural units derived from (c): 5 to 60 mol %.

[0111] When the ratio of the structural units of the resin [K2] is within the above range, the composition tends to have excellent storage stability and developability when forming a colored pattern.

[0112] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0113] Resin [K3] can be produced by adding a cyclic ether having 2 to 4 carbon atoms contained in (b) to a carboxylic acid and / or a carboxylic acid anhydride contained in (a) to a copolymer of (a) and (c).

[0114] First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each of them is preferably the same as that described for resin [K1].

[0115] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b).

[0116] Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b) the carboxylic acid or carboxylic anhydride is reacted with the cyclic ether in the presence of a reaction catalyst (e.g., an organic phosphorus compound, a metal complex, an amine compound, etc.) and a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.) at a temperature of 60°C or higher and 130°C or lower for 1 hour to 10 hours, thereby producing resin [K3].

[0117] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, a decrease in the residual film rate after development of the cured film can be suppressed when the curable composition is cured at low temperature.

[0118] Examples of organic phosphorus compounds used as reaction catalysts include triphenylphosphine. Examples of amine compounds that can be used as reaction catalysts include aliphatic tertiary amine compounds and aliphatic quaternary ammonium salt compounds, and specific examples thereof include tris(dimethylaminomethyl)phenol, triethylamine, tetrabutylammonium bromide, and tetrabutylammonium chloride. The reaction catalyst is preferably an organic phosphorus compound.

[0119] The amount of the reaction catalyst used is preferably 0.001 parts by mass or more and 5 parts by mass or less per 100 parts by mass of the total amount of (a), (b) and (c).

[0120] The amount of the polymerization inhibitor used is preferably 0.001 parts by mass or more and 5 parts by mass or less per 100 parts by mass of the total amount of (a), (b) and (c).

[0121] The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0122] Resin [K4] is a resin obtained by further reacting resin [K3] with a carboxylic acid anhydride. The carboxylic acid anhydride is reacted with a hydroxy group generated by the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether. Examples of carboxylic acid anhydrides include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.5 mol or more and 1 mol or less per 1 mol of (b) used.

[0123] Resin [K5] is obtained in the first step by the same method as in the production of Resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation.

[0124] The proportions of the structural units derived from (b) and (c) relative to the total number of moles of all structural units constituting the copolymer are preferably: structural units derived from (b): 5 mol% to 95 mol% structural units derived from (c): 5 mol% to 95 mol%, more preferably structural units derived from (b): 10 mol% to 90 mol%, and structural units derived from (c): 10 mol% to 90 mol%.

[0125] Resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic anhydride contained in (a) under the same conditions as in the production method of Resin [K3].

[0126] The amount of (a) used to react with the copolymer is preferably 5 to 120 moles, more preferably 20 to 110 moles, per 100 moles of (b).

[0127] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride.

[0128] Examples of carboxylic acid anhydrides include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0129] The amount of the carboxylic acid anhydride used is preferably 0.1 to 1 mol, more preferably 0.2 to 1 mol, and even more preferably 0.3 to 1 mol, per 1 mol of the amount of (a) used.

[0130] Examples of the resins [K1], [K2], [K3], [K4], [K5] and [K6] include resins [K1] such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, (meth)acrylic acid / succinic acid mono[2-(meth)acryloyloxyethyl] / dicyclopentanyl (meth)acrylate / methyl (meth)acrylate copolymer; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl acrylate / (meth) acrylic acid / methyl (meth) acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6]decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer and other resins [K2]; resins obtained by adding glycidyl (meth)acrylate to a benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, and resins obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer and other resins [K3]; Resins [K4] such as a resin obtained by adding glycidyl (meth)acrylate to a dicyclopentanyl (meth)acrylate / methyl (meth)acrylate / (meth)acrylic acid copolymer and further bonding with tetrahydrophthalic anhydride or succinic anhydride via an ester bond, and a resin obtained by adding glycidyl (meth)acrylate to a dicyclopentanyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / (meth)acrylic acid copolymer and further bonding with tetrahydrophthalic anhydride or succinic anhydride via an ester bond; resins [K5] such as a resin obtained by adding (meth)acrylic acid to a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer and a resin obtained by adding (meth)acrylic acid to a tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymer; Examples of the resin [K6] include a resin obtained by adding (meth)acrylic acid to a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, and further bonding with tetrahydrophthalic anhydride or succinic anhydride via an ester bond; and a resin obtained by adding (meth)acrylic acid to a copolymer of dicyclopentanyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate, and further bonding with tetrahydrophthalic anhydride or succinic anhydride via an ester bond.

[0131] The resin (C) contained in the curable composition preferably contains at least one selected from the group consisting of resin [K1], resin [K2], resin [K3], resin [K4], resin [K5] and resin [K6], more preferably contains at least one selected from the group consisting of resin [K3], resin [K4], resin [K5] and resin [K6], further preferably contains at least one selected from the group consisting of resin [K4] and resin [K6], with resin [K6] being particularly preferred.

[0132] Further examples of resin (C) include the resins described in JP 2018-123274 A. Examples of such resins include polymers (hereinafter also referred to as "resin (Ca)") that have double bonds in their side chains, contain structural units (α) represented by the following formula (I) and structural units (β) represented by the following formula (II) in their main chains, and further contain acid groups:

[0133] The acid group can be introduced into the resin (Ca) by, for example, including a structural unit (γ) derived from an acid group-containing monomer (e.g., (meth)acrylic acid, etc.) The resin (Ca) preferably includes the structural units (α), (β), and (γ) in the main chain skeleton.

[0134]

[0135] [In the formula, R Ａ and R Ｂ are the same or different and represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms. n represents the average number of repeating units of the structural unit represented by formula (I) and is a number of 1 or more.

[0136]

[0137] [In the formula, R Ｃ are the same or different and represent a hydrogen atom or a methyl group. Ｄare the same or different and represent a linear or branched hydrocarbon group having 4 to 20 carbon atoms. m represents the average number of repeating units of the structural unit represented by formula (II) and is a number of 1 or greater.] In resin (Ca), from the viewpoint of the storage stability of resin (Ca), the content of structural unit (α) is, for example, 0.5% by mass or more and 50% by mass or less, preferably 1% by mass or more and 40% by mass or less, and more preferably 5% by mass or more and 30% by mass or less, relative to 100% by mass of the total amount of all monomer units that form the main chain skeleton of resin (Ca). n in formula (I) represents the average number of repeating units of structural unit (α) in resin (Ca), and n can be set so that the content of structural unit (α) falls within the above range.

[0138] From the viewpoint of solvent resistance, the content of the structural unit (β) is, for example, 10% by mass or more and 90% by mass or less, preferably 20% by mass or more and 80% by mass or less, and more preferably 30% by mass or more and 75% by mass or less, relative to 100% by mass of the total amount of all monomer units that contribute to the main chain skeleton of the resin (Ca). m in formula (II) represents the average number of repeating units of the structural unit (β) in the resin (Ca), and m can be set so that the content of the structural unit (β) falls within the above-mentioned range.

[0139] From the viewpoint of the solubility of the resin (Ca) in the solvent (J) and the like, the content of the structural unit (γ) is, for example, 0.5% by mass or more and 50% by mass or less, preferably 2% by mass or more and 50% by mass or less, and more preferably 5% by mass or more and 45% by mass or less, relative to 100% by mass of the total amount of all monomer units that constitute the main chain skeleton of the resin (Ca).

[0140] In the present invention, it is important that the value X calculated from the acid value and weight average molecular weight Mw of resin (C) using the following formula (1) is 10 or more and 59.75 or less. By setting the value X within this range, it is possible to suppress a decrease in the development residual film rate (hereinafter sometimes simply referred to as residual film rate) of the cured film when the curable composition is cured at low temperature. The value X is preferably 12.50 or more, more preferably 16.50 or more, and is preferably 58 or less, more preferably 56.25 or less. The value X is preferably 12.50 or more and 56.25 or less, more preferably 16.50 or more and 56.25 or less. X={acid value (mg-KOH / g)×weight average molecular weight Mw} / 10,000 ... (1)

[0141] The acid value of resin (C) is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (C), and can be determined, for example, by titration with an aqueous potassium hydroxide solution. Specifically, it can be measured according to the measurement method described in the Examples section below. Alternatively, the acid value of resin (C) contained in the composition can be determined, for example, by structural analysis of the resin (C).

[0142] The weight average molecular weight Mw of the resin (C) is a weight average molecular weight measured by GPC in terms of standard polystyrene, and can be measured according to the measurement method described in the Examples section below. Alternatively, the Mw of the resin (C) contained in the curable composition may be measured using GPC.

[0143] The weight average molecular weight Mw of resin (C) is not particularly limited as long as it satisfies the above-mentioned value X, but is, for example, 1,000 or more, preferably 3,000 or more, more preferably 5,000 or more, and even more preferably 5,500 or more. It is also, for example, 100,000 or less, preferably 50,000 or less, more preferably 20,000 or less, more preferably 8,000 or less, and even more preferably 7,500 or less. The weight average molecular weight Mw of resin (C) is preferably 5,000 or more and 8,000 or less, and more preferably 5,500 or more and 7,500 or less. In particular, from the viewpoint of improving patterning properties after exposure and development, Mw is preferably 5,000 or more. The Mw of resin (C) can be adjusted by appropriately combining reaction conditions such as the selection of raw materials used, the charging method, the reaction temperature and time, etc.

[0144] The acid value of resin (C) is not particularly limited as long as it satisfies the above-mentioned value X, but is preferably 150 mg-KOH / g or less, more preferably 110 mg-KOH / g or less, even more preferably 85 mg-KOH / g or less, particularly preferably 80 mg-KOH / g or less, most preferably 75 mg-KOH / g or less, and preferably 20 mg-KOH / g or more, more preferably 25 mg-KOH / g or more, and even more preferably 30 mg-KOH / g or more. The acid value of resin (C) is preferably 25 mg-KOH / g or more and 80 mg-KOH / g or less, and more preferably 30 mg-KOH / g or more and 75 mg-KOH / g or less. The acid value of resin (C) can be adjusted by the content of a monomer component having an acid group (e.g., the above (a)) or the content of a carboxylic acid anhydride.

[0145] It is also important that the double bond equivalent of resin (C) is 100 g / eq or more but less than 600 g / eq. By having the double bond equivalent within this range, a decrease in the residual film rate of the cured film can be suppressed when the curable composition is cured at low temperatures. The double bond equivalent of resin (C) is preferably 200 g / eq or more, more preferably 250 g / eq or more, even more preferably 300 g / eq or more, and preferably 500 g / eq or less, more preferably 450 g / eq or less, and even more preferably 400 g / eq or less. The double bond equivalent of resin (C) is preferably 250 g / eq or more but less than 450 g / eq, more preferably 300 g / eq or more but less than 400 g / eq. An example of a resin having the above-mentioned double bond equivalent is a (meth)acrylic resin. Resin (C) is preferably a (meth)acrylic resin.

[0146] The content of resin (C) in the curable composition is, for example, 5% by mass or more and 80% by mass or less, preferably 10% by mass or more and 70% by mass or less, more preferably 13% by mass or more and 60% by mass or less, and even more preferably 17% by mass or more and 55% by mass or less, relative to the total amount of solids in the curable composition. When the content of resin (C) is within the above range, a decrease in the residual film rate of the cured film obtained by curing a coating film of the curable composition at a low temperature can be suppressed.

[0147] The mass ratio (A / C) of the semiconductor particles (A) to the resin (C) is preferably 0.65 or more, more preferably 1 or more, and even more preferably 1.5 or more, and is preferably less than 10, more preferably 8 or less, and even more preferably 5 or less.

[0148] <Light Scattering Agent (B)> Examples of the light scattering agent (B) include inorganic particles such as metal or metal oxide particles and glass particles. Examples of metal oxides include TiO ２ , SiO ２ , BaTiO ３ , ZnO, etc., and TiO is preferred because it scatters light efficiently. ２ The particle diameter of the light scattering agent (B) is, for example, about 0.03 μm or more and 20 μm or less, preferably 0.05 μm or more and 1 μm or less, and more preferably 0.05 μm or more and 0.5 μm or less.

[0149] The light scattering agent (B) may be a dispersion prepared by dispersing a light scattering agent in advance in a part or all of the solvent (J) using a dispersant (I). Commercially available dispersants (I) may be used. Examples of commercially available dispersants include DISPERBYK-101, 102, 103, 106, 107, 108, 109, 110, 111, 116, 118, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 192, and 20 manufactured by BYK Japan. 00, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155; ANTI-TERRA-U, U100, 203, 204, 250; BY K-P104, P104S, P105, 220S, 6919; BYK-LPN6919, 21116; LACTIMON, LACTIMON-WS; Bykumen et al. SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, and the like manufactured by Lubrizol Japan Corporation; EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, and the like manufactured by BASF; Examples include Ajisper PA111, PB711, PB821, PB822, and PB824 manufactured by Ajinomoto Fine-Techno Co., Ltd.

[0150] The content of the light scattering agent (B) in the curable composition is, for example, from 0.001% by mass to 50% by mass, relative to the total amount of solids in the curable composition. From the viewpoint of improving the light scattering ability and luminous intensity when a cured film of the curable composition is used as a wavelength conversion layer, the content is preferably from 1% by mass to 40% by mass, more preferably from 2% by mass to 30% by mass, even more preferably from 5% by mass to 30% by mass, and still more preferably from 8% by mass to 30% by mass.

[0151] <Polymerizable Compound (D)> The polymerizable compound (D) is a compound that can be polymerized by an active radical, an acid, or the like generated from the polymerization initiator (E) described below. Examples of the polymerizable compound (D) include photopolymerizable compounds such as compounds having an ethylenically unsaturated bond, such as (meth)acrylic acid ester compounds. Another example of the polymerizable compound (D) is a thermally polymerizable compound. The curable composition may contain two or more types of polymerizable compounds (D).

[0152] Examples of the polymerizable compound (D) include a photopolymerizable compound (Dα) having two ethylenically unsaturated bonds in the molecule and a photopolymerizable compound (Dβ) having three or more ethylenically unsaturated bonds in the molecule. The photopolymerizable compound (Dβ) preferably has six or fewer ethylenically unsaturated bonds in the molecule. The ethylenically unsaturated bonds are preferably (meth)acryloyloxy groups. The weight-average molecular weight of the polymerizable compound (D) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less. The polymerizable compound (D) preferably contains one or more selected from the photopolymerizable compound (Dα) and the photopolymerizable compound (Dβ), and more preferably contains one or more photopolymerizable compounds (Dβ). The photopolymerizable compound (D) also preferably contains one or more photopolymerizable compounds (Dα) and one or more photopolymerizable compounds (Dβ).

[0153] Examples of the photopolymerizable compound (Dα) having two ethylenically unsaturated bonds in the molecule include bifunctional (meth)acrylic compounds, such as alkylene glycol di(meth)acrylates, polyoxyalkylene glycol di(meth)acrylates, halogen-substituted alkylene glycol di(meth)acrylates, di(meth)acrylates of aliphatic polyols, di(meth)acrylates of hydrogenated dicyclopentadiene or tricyclodecane dialkanol, di(meth)acrylates of dioxane glycol or dioxane dialkanol, di(meth)acrylates of alkylene oxide adducts of bisphenol A or bisphenol F, and epoxy di(meth)acrylates of bisphenol A or bisphenol F.

[0154] More specific examples of the bifunctional (meth)acrylic compound include ethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol di(meth)acrylate, ditrimethylolpropane di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, and di(meth)acrylate of neopentyl glycol ester of hydroxypivalic acid. 2,2-bis[4-(meth)acryloyloxyethoxyethoxyphenyl]propane, 2,2-bis[4-(meth)acryloyloxyethoxyethoxycyclohexyl]propane, hydrogenated dicyclopentadienyl di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, 1,3-dioxane-2,5-diyl di(meth)acrylate [also known as dioxane glycol di(meth)acrylate], acrylate of hydroxypivalaldehyde and trimethylolpropane Examples include di(meth)acrylate of a cetal compound [chemical name: 2-(2-hydroxy-1,1-dimethylethyl)-5-ethyl-5-hydroxymethyl-1,3-dioxane], tris(hydroxyethyl)isocyanurate di(meth)acrylate, di(meth)acrylate of ethoxylated bisphenol A, di(meth)acrylate of propoxylated bisphenol A, di(meth)acrylate of ethoxylated bisphenol F, and di(meth)acrylate of propoxylated bisphenol F.

[0155] The photopolymerizable compound (Dα) having two ethylenically unsaturated bonds in one molecule is preferably a photopolymerizable compound (Dα1) having one or more cyclic hydrocarbon groups and two ethylenically unsaturated bonds in one molecule, and the polymerizable compound (D) preferably contains one or more photopolymerizable compounds (Dα1). In the photopolymerizable compound (Dα1), the cyclic hydrocarbon group is preferably an aromatic hydrocarbon group, and the aromatic hydrocarbon group is more preferably a phenylene group. Furthermore, in the photopolymerizable compound (Dα1), the number of cyclic hydrocarbon groups in one molecule is preferably two. Specific examples of the photopolymerizable compound (Dα1) include di(meth)acrylate of ethoxylated bisphenol A, di(meth)acrylate of propoxylated bisphenol A, di(meth)acrylate of ethoxylated bisphenol F, and di(meth)acrylate of propoxylated bisphenol F.

[0156] Examples of the polymerizable compound (Dβ) having three or more ethylenically unsaturated bonds in the molecule include a compound (Dβ1) having three or more ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) in the molecule and having an acidic functional group, and a compound (Dβ2) having three or more ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) in the molecule and not having an acidic functional group. The polymerizable compound (D) preferably contains at least one of the compounds (Dβ1) and (Dβ2), and more preferably contains at least one of the compound (Dβ1). Examples of the acidic functional group include a carboxy group, a sulfonic acid group, a phosphate group, and the like. Among these, the acidic functional group is preferably a carboxy group.

[0157] The number of ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups) contained in one molecule of compound (Dβ1) is, for example, 3 or more and 6 or less, preferably 3 or more and 5 or less, and more preferably 3. The number of acidic functional groups contained in one molecule of compound (Dβ1) is 1 or more, preferably 1. When two or more acidic functional groups are contained, the respective acidic functional groups may be different or the same, but it is preferable that the compound (Dβ1) has at least one carboxy group.

[0158] Examples of the compound (Dβ1) include compounds obtained by esterifying a compound having three or more (meth)acryloyloxy groups and hydroxyl groups, such as pentaerythritol tri(meth)acrylate or dipentaerythritol penta(meth)acrylate, with a dicarboxylic acid or dicarboxylic acid anhydride. Examples of the compound include a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate with succinic acid, a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate with succinic acid, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate with maleic acid, and a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate with maleic acid. Among these, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate with succinic acid is preferred.

[0159] Examples of commercially available products of compound (Dβ1) include "Aronix M-510" manufactured by Toagosei Co., Ltd., which contains a dibasic acid anhydride adduct of pentaerythritol tri(meth)acrylate as the main component, and "Aronix M-520D" manufactured by Toagosei Co., Ltd., which contains a dibasic acid anhydride adduct of dipentaerythritol penta(meth)acrylate as the main component. These commercially available products have a carboxy group as the acidic functional group.

[0160] The compound (Dβ2) preferably has 3 to 6 ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups), and more preferably has 4 to 6 ethylenically unsaturated bonds (particularly (meth)acryloyloxy groups).

[0161] Examples of the compound (Dβ2) include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris( 2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc. Among these, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc. are preferred.

[0162] The polymerizable compound (D) in the curable composition is preferably the compound (Dα) (particularly the compound (Dα1)), because by including the compound (Dα) it is possible to suppress a decrease in the residual film rate of the cured film obtained by curing a coating film of the curable composition at a low temperature, and it is also possible to reduce the residue after development of the curable composition. By including the compound (Dβ), it is possible to suppress a decrease in the residual film rate of the cured film obtained by curing a coating film of the curable composition at a low temperature, and it is also possible to improve the curability during exposure and the patterning property during development, and it is also possible to improve the dispersibility of the semiconductor particles (A), and it is also possible to improve the luminescence intensity when the cured film is used as a wavelength conversion layer.

[0163] In 100% by mass of the polymerizable compound (D) contained in the curable composition, the compound (Dα) (compound (Dα1)) is preferably 30% by mass or more, more preferably 40% by mass or more, even more preferably 50% by mass or more, and may be 70% by mass or less. In 100% by mass of the polymerizable compound (D) contained in the curable composition, the compound (Dβ) is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and may be 100% by mass or 60% by mass or less.

[0164] When the polymerizable compound (D) in the curable composition contains both the compound (Dα) and the compound (Dβ), it preferably contains the compound (Dα1) and (Dβ1), and the total content of the compound (Dα1) and the compound (Dβ1) relative to 100% by mass of the polymerizable compound (D) is preferably 70% by mass or more, more preferably 85% by mass or more, and may be 100% by mass. The content of the compound (Dα1) relative to 100% by mass of the total amount of the compound (Dα1) and the compound (Dβ1) is preferably more than 50% by mass, more preferably 53% by mass or more, even more preferably 55% by mass or more, and may be 70% by mass or less.

[0165] When the polymerizable compound (D) in the curable composition contains both the compound (Dβ1) and the compound (Dβ2), the total content of the compound (Dβ1) and the compound (Dβ2) relative to 100% by mass of the polymerizable compound (D) is preferably 70% by mass or more, more preferably 85% by mass or more, and may be 100% by mass. The content of the compound (Dβ2) relative to 100% by mass of the total amount of the compound (Dβ1) and the compound (Dβ2) is preferably more than 50% by mass, more preferably 53% by mass or more, even more preferably 55% by mass or more, and may be 70% by mass or less.

[0166] The content of the polymerizable compound (D) in the curable composition (total amount when multiple types are contained) is preferably 3% by mass or more and 30% by mass or less, more preferably 4% by mass or more and 20% by mass or less, and even more preferably 5% by mass or more and 15% by mass or less, relative to 100% by mass of the total solid content of the curable composition. When the content of the polymerizable compound (D) is within the above range, a decrease in the residual film rate of the cured film obtained by curing a coating film of the curable composition at a low temperature can be suppressed.

[0167] From the viewpoint of suppressing a decrease in the residual film rate of the cured film, the mass ratio (C / D) of the resin (C) to the polymerizable compound (D) in the curable composition is preferably 2 or more, more preferably 2.3 or more, even more preferably 2.5 or more, and is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. When the mass ratio (C / D) of the resin (C) to the polymerizable compound (D) satisfies the above range, it is preferable that the photopolymerizable compound (D) contains one or more photopolymerizable compounds (Dα1), and it is more preferable that the photopolymerizable compound (D) contains one or more photopolymerizable compounds (Dα1) and one or more photopolymerizable compounds (Dβ1).

[0168] <Polymerization initiator (E)> The polymerization initiator (E) is a compound that generates an active radical, an acid, or the like by the action of light or heat, and can initiate polymerization of the polymerizable compound (D). The curable composition can contain one or more polymerization initiators (E).

[0169] Examples of the polymerization initiator (E) include oxime compounds, such as compounds represented by formula (EA). When the polymerization initiator (E) contains a compound represented by formula (EA), it is possible to suppress a decrease in the residual film rate of the cured film when the curable composition is cured at a low temperature, and it is also advantageous from the viewpoint of improving patterning after exposure and development. Furthermore, when the polymerization initiator (E) contains a compound represented by formula (EA), it is possible to exhibit the effect of improving the luminescence intensity (fluorescence luminescence intensity) evaluated in the examples described below.

[0170] [In the formula, R ｅａ１ represents a branched hydrocarbon group having 3 to 20 carbon atoms which may have a substituent. ｅａ２ ~R ｅａ５each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. n represents an integer of 0 to 4. -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO- or -OCO-.]

[0171] R ｅａ１ Examples of the branched hydrocarbon group having 3 to 20 carbon atoms represented by the formula (I) include branched saturated hydrocarbon groups having 3 to 20 carbon atoms and branched unsaturated hydrocarbon groups having 3 to 20 carbon atoms.

[0172] R ｅａ１Examples of the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by the formula (I) include a 1-methylethyl group (isopropyl group), a 1-methylpropyl group (sec-butyl group), a 2-methylpropyl group (isobutyl group), a 1,1-dimethylethyl group (tert-butyl group), a 1,1-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1,1-dimethylbutyl group, and a 2,2-dimethylbutyl group. , 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1,1-dimethylpentyl group, 2,2-dimethylpentyl group, 3,3-dimethylpentyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentyl group, 2,3-dimethylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3 -ethylpentyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 1,1-dimethylhexyl group, 2,2-dimethylhexyl group, 3,3-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 2,3-dimethylhexyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group, 1,1-dimethylhexyl group butyl group, 2,2-dimethylheptyl group, 3,3-dimethylheptyl group, 1,2-dimethylheptyl group, 1,3-dimethylheptyl group, 2,3-dimethylheptyl group, 1-ethylheptyl group, 2-ethylheptyl group, 3-ethylheptyl group, 1-methyloctyl group, 2-methyloctyl group, 3-methyloctyl group, 4-methyloctyl group, 1,1-dimethyloctyl group, 2,2-dimethyloctyl group, 3,3-dimethyloctyl group, 1,2-dimethyloctyl group, 1,3-dimethyloctyl group, 2,branched alkyl groups such as a 3-dimethyloctyl group, a 1-ethyloctyl group, a 2-ethyloctyl group, a 3-ethyloctyl group, a 1-methylnonyl group, a 2-methylnonyl group, a 3-methylnonyl group, a 4-methylnonyl group, a dimethylnonyl group, an ethylnonyl group, a methyldecyl group, a dimethyldecyl group, an ethyldecyl group, a methylundecyl group, a dimethylundecyl group, an ethylundecyl group, and a methyldodecyl group; ｅａ１ The branched alkyl group represented by R may be a primary branched alkyl group, a secondary branched alkyl group, or a tertiary branched alkyl group. ｅａ１ The number of carbon atoms in the branched saturated hydrocarbon group represented by the formula (I) is preferably 4 or more, more preferably 5 or more, and is preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.

[0173] R ｅａ１ The branched unsaturated hydrocarbon group represented by the formula (I) is the same as the R ｅａ１ Examples include groups in which at least one carbon-carbon single bond contained in a branched saturated hydrocarbon group represented by the formula: R ｅａ１ Examples of the branched unsaturated hydrocarbon group represented by the formula (I) include alkenyl groups such as an isopropenyl group, an isobutenyl group, an isopentenyl group, an isohexenyl group, an isoheptenyl group, an isooctenyl group, an isononyl group, and an isodecenyl group; and alkynyl groups such as an isopropynyl group, an isobutynyl group, an isopentynyl group, an isohexynyl group, an isoheptynyl group, an isooctynyl group, an isononynyl group, and an isodecynyl group. ｅａ１ The number of carbon atoms in the branched unsaturated hydrocarbon group represented by the formula (I) is preferably 4 or more, more preferably 5 or more, and is preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.

[0174] R ｅａ２ , R ｅａ３ , R ｅａ４ and R ｅａ５Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R include saturated hydrocarbon groups having 1 to 20 carbon atoms, unsaturated hydrocarbon groups having 2 to 20 carbon atoms, and aromatic hydrocarbon groups having 6 to 20 carbon atoms. ｅａ２ , R ｅａ３ , R ｅａ４ and R ｅａ５ The hydrocarbon groups represented by the formula (I) may be the same or different.

[0175] Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups. The number of carbon atoms in the saturated hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 10, and even more preferably 1 to 8.

[0176] Examples of the unsaturated hydrocarbon group having 2 to 20 carbon atoms include alkenyl groups such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, hexadecenyl, octadecenyl, and icosenyl; alkynyl groups such as ethynyl, propynyl, hexynyl, decynyl, and icosenyl; and cycloalkenyl groups such as cyclopentenyl, cyclohexenyl, and cycloheptenyl. The number of carbon atoms in the unsaturated hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 2 to 10.

[0177] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, a benzyl group, a phenylethyl group, a phenylbutyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

[0178] R ｅａ１ , R ｅａ２ , R ｅａ３ , R ｅａ４ and R ｅａ５ Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include a halogen atom, a cyano group, and a nitro group. The halogen atom is preferably a fluorine atom, a bromine atom, a chlorine atom, or an iodine atom.

[0179] The —CH2— contained in the hydrocarbon group may be replaced with —O—, —S—, —CO— or —OCO—, provided that adjacent —CH2—s are not simultaneously replaced with the same type of group, and the terminal —CH2— is not replaced.

[0180] n represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably an integer of 0 or 1, and even more preferably 0.

[0181] *-OCO-R ｅａ４ The bonding position of the *-OCO-R group (* represents a bond to the phenyl group) is ｅａ４ The group may be bonded to any of the 2-, 3-, or 4-positions of the phenyl group, preferably the 3- or 4-position, more preferably the 4-position.

[0182] R ｅａ１The branched hydrocarbon group having 3 to 20 carbon atoms, represented by the formula (I), is preferably a branched saturated hydrocarbon group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 3 to 20 carbon atoms, and even more preferably a branched alkyl group having 3 to 10 carbon atoms, and is preferably one or more selected from the group consisting of a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1-ethylpentyl group, a 2-ethylpentyl group, a 3-ethylpentyl group, a 1-methylhexyl group, a 2-methylhexyl group, a 3-methylhexyl group, a 1-ethylhexyl group, a 2-ethylhexyl group, a 3-ethylhexyl group, a 1-methylheptyl group, a 2-methylheptyl group, a 3-methylheptyl group, a 1-ethylheptyl group, a 2-ethylheptyl group, and a 3-ethylheptyl group.

[0183] R ｅａ２ , R ｅａ３ , R ｅａ４ and R ｅａ５ The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an unsaturated hydrocarbon group having 2 to 20 carbon atoms, more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, even more preferably a chain-like saturated hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a chain-like alkyl group having 1 to 8 carbon atoms. ｅａ２ is preferably a chain alkyl group having 1 to 8 carbon atoms, more preferably a chain alkyl group having 1 to 6 carbon atoms. ｅａ３ is preferably a chain alkyl group having 1 to 8 carbon atoms, more preferably a chain alkyl group having 1 to 3 carbon atoms. ｅａ４ is preferably a chain alkyl group having 1 to 8 carbon atoms, more preferably a chain alkyl group having 1 to 3 carbon atoms. ｅａ５ is preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and more preferably a linear or branched alkyl group having 1 to 6 carbon atoms.

[0184] Furthermore, examples of the polymerization initiator (E) that is an oxime compound include a compound represented by formula (EB): When the polymerization initiator (E) contains a compound represented by formula (EB), a decrease in the residual film rate of the cured film can be suppressed when the curable composition is cured at a low temperature.

[0185] [In the formula, Rｅｂ１ represents a branched hydrocarbon group having 3 to 20 carbon atoms which may have a substituent. ｅｂ２ ~R ｅｂ４ each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and m represents an integer of 0 to 4. -CH contained in the hydrocarbon group ２ - may be replaced by -O-, -S-, -CO- or -OCO-.]

[0186] R ｅｂ１ Examples of the branched hydrocarbon group having 3 to 20 carbon atoms represented by the formula (I) include branched saturated hydrocarbon groups having 3 to 20 carbon atoms and branched unsaturated hydrocarbon groups having 3 to 20 carbon atoms.

[0187] R ｅｂ１ Examples of the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by R ｅａ１ Examples of the branched saturated hydrocarbon group having 3 to 20 carbon atoms represented by the formula R include the same as those exemplified above. ｅｂ１ The branched alkyl group represented by R may be a primary branched alkyl group, a secondary branched alkyl group, or a tertiary branched alkyl group. ｅｂ１ The number of carbon atoms in the branched saturated hydrocarbon group represented by the formula (I) is preferably 4 or more, more preferably 5 or more, and is preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.

[0188] R ｅｂ１ The branched unsaturated hydrocarbon group represented by the formula (I) is the same as the R ｅｂ１ Examples include groups in which at least one carbon-carbon single bond contained in a branched saturated hydrocarbon group represented by the formula: R ｅｂ１Examples of the branched unsaturated hydrocarbon group represented by the formula (I) include alkenyl groups such as an isopropenyl group, an isobutenyl group, an isopentenyl group, an isohexenyl group, an isoheptenyl group, an isooctenyl group, an isononyl group, and an isodecenyl group; and alkynyl groups such as an isopropynyl group, an isobutynyl group, an isopentynyl group, an isohexynyl group, an isoheptynyl group, an isooctynyl group, an isononynyl group, and an isodecynyl group. ｅｂ１ The number of carbon atoms in the branched unsaturated hydrocarbon group represented by the formula (I) is preferably 4 or more, more preferably 5 or more, and is preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.

[0189] R ｅｂ２ , R ｅｂ３ and R ｅｂ４ Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R include saturated hydrocarbon groups having 1 to 20 carbon atoms, unsaturated hydrocarbon groups having 2 to 20 carbon atoms, and aromatic hydrocarbon groups having 6 to 20 carbon atoms. ｅｂ２ , R ｅｂ３ and R ｅｂ４ The hydrocarbon groups represented by the formula (I) may be the same or different.

[0190] Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups. The number of carbon atoms in the saturated hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 10, and even more preferably 1 to 8.

[0191] Examples of the unsaturated hydrocarbon group having 2 to 20 carbon atoms include alkenyl groups such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, hexadecenyl, octadecenyl, and icosenyl; alkynyl groups such as ethynyl, propynyl, hexynyl, decynyl, and icosenyl; and cycloalkenyl groups such as cyclopentenyl, cyclohexenyl, and cycloheptenyl. The number of carbon atoms in the unsaturated hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 2 to 10.

[0192] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, a benzyl group, a phenylethyl group, a phenylbutyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

[0193] R ｅｂ１ , R ｅｂ２ , R ｅｂ３ and R ｅｂ４ Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include a halogen atom, a cyano group, and a nitro group. The halogen atom is preferably a fluorine atom, a bromine atom, a chlorine atom, or an iodine atom, and more preferably a fluorine atom.

[0194] The hydrocarbon group contains —CH ２ - may be replaced by -O-, -S-, -CO- or -OCO-, particularly by -O-, and may be replaced by an adjacent -CH ２ - is not simultaneously substituted with the same group, and the terminal -CH ２ - is never replaced.

[0195] m represents an integer of 0 to 4, preferably an integer of 1 to 3, more preferably an integer of 2 or 3, and even more preferably 3.

[0196] When m is 1 or more, *-R ｅｂ４is bonded to at least one of the 2-, 4- and 6-positions of the phenyl group, ｅｂ４ (* represents a bond to the phenyl group) is preferably bonded, and *-R ｅｂ４ *-R is bonded to at least two of the 2-, 4- and 6-positions of the phenyl group. ｅｂ４ is more preferably bonded, and *-R ｅｂ４ *-R is bonded to all of the 2-, 4-, and 6-positions of the phenyl group. ｅｂ４ is more preferably bonded.

[0197] R ｅｂ１ The branched hydrocarbon group having 3 to 20 carbon atoms, represented by the formula (I), is preferably a branched saturated hydrocarbon group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 3 to 20 carbon atoms, and even more preferably a branched alkyl group having 3 to 10 carbon atoms, and is preferably one or more selected from the group consisting of a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1-ethylpentyl group, a 2-ethylpentyl group, a 3-ethylpentyl group, a 1-methylhexyl group, a 2-methylhexyl group, a 3-methylhexyl group, a 1-ethylhexyl group, a 2-ethylhexyl group, a 3-ethylhexyl group, a 1-methylheptyl group, a 2-methylheptyl group, a 3-methylheptyl group, a 1-ethylheptyl group, a 2-ethylheptyl group, and a 3-ethylheptyl group.

[0198] R ｅｂ２ The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 17 carbon atoms, still more preferably an aromatic hydrocarbon group having 7 to 15 carbon atoms, and particularly preferably an aromatic hydrocarbon group having 8 to 13 carbon atoms. In any of these preferred embodiments, the hydrocarbon group has 1 to 8 (particularly 1 to 5) fluorine atoms as a substituent, and 1 to 2 -CH ２ It is preferred that the structure has - replaced by -O-.

[0199] R ｅｂ２ The aromatic hydrocarbon group having 8 to 13 carbon atoms, which is a preferred embodiment of (eb2-1), is preferably any one of the following (eb2-1) to (eb2-6).

[0200]

[0201] R ｅｂ３ and R ｅｂ４ The hydrocarbon groups having 1 to 20 carbon atoms represented by the formula (I) are each independently preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an unsaturated hydrocarbon group having 2 to 20 carbon atoms, more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, even more preferably a chain-like saturated hydrocarbon group having 1 to 10 carbon atoms, still more preferably a chain-like alkyl group having 1 to 8 carbon atoms, and particularly preferably a chain-like alkyl group having 1 to 3 carbon atoms.

[0202] In addition, in formula (EB), —CH contained in the hydrocarbon group ２ When - is replaced by -O-, -S-, -CO- or -OCO-, the number of carbon atoms in the replaced part is the same as the number of carbon atoms in the -CH before replacement. ２ - The number of carbon atoms is counted.

[0203] Examples of the polymerization initiator (E) other than the compounds represented by formula (EA) and formula (EB) include photopolymerization initiators such as oxime compounds (excluding the compounds represented by formula (EA) and the compounds represented by formula (EB)), alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine compounds, and thermal polymerization initiators such as azo compounds and organic peroxides.

[0204] An example of the oxime compound (excluding the compounds represented by formula (EA) and formula (EB)) is an oxime compound having a first molecular structure represented by the following formula (1). Hereinafter, this oxime compound will also be referred to as "oxime compound (1)."

[0205]

[0206] Inclusion of the oxime compound (1) as the polymerization initiator (E) can be advantageous from the viewpoint of improving the luminescence intensity. One of the reasons for this effect is presumed to be that the unique molecular structure of the oxime compound (1) results in a large change in the absorption wavelength of the oxime compound (1) before and after its cleavage (decomposition), which is necessary for the oxime compound (1) to initiate photopolymerization, and therefore the oxime compound (1) has a high photoradical polymerization initiation ability.

[0207] In formula (1), R １ is R １１ , OR １１ , C.O.R. １１ , S.R. １１ , C.O.R. １２ R １３ Or CN.

[0208] R １１ , R １２ and R １３ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0209] R １１ , R １２ or R １３ The hydrogen atom of the group represented by ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , CN, a halogen atom, or COOR ２１ may be substituted with.

[0210] R ２１ , R ２２ and R ２３ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0211] R ２１ , R ２２ or R ２３ The hydrogen atom of the group represented by the formula (I) may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.

[0212] R １１ , R１２ , R １３ , R ２１ , R ２２ or R ２３ has an alkylene moiety, the alkylene moiety is preferably —O—, —S—, —COO—, —OCO—, —NR ２４ -, -NR ２４ CO-, -NR ２４ COO-,-OCONR ２４ It may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-.

[0213] R ２４ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0214] R １１ , R １２ , R １３ , R ２１ , R ２２ or R ２３ When the group represented by R １２ and R １３ and R ２２ and R ２３ may be joined together to form a ring.

[0215] * represents a bond to a second molecular structure, which is a molecular structure other than the first molecular structure that the oxime compound (1) has.

[0216] R in formula (1) １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４Examples of the alkyl group having 1 to 20 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a tert-pentyl group, a hexyl group, a heptyl group, an octyl group, an isooctyl group, a 2-ethylhexyl group, a tert-octyl group, a nonyl group, an isononyl group, a decyl group, an isodecyl group, an undecyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an icosyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0217] R in formula (1) １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４ Examples of the aryl group having 6 to 30 carbon atoms represented by the formula (I) include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a phenyl group substituted with one or more of the above-mentioned alkyl groups, a biphenylyl group, a naphthyl group, and an anthryl group.

[0218] R in formula (1) １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４ Examples of the aralkyl group having 7 to 30 carbon atoms represented by the formula (I) include a benzyl group, an α-methylbenzyl group, an α,α-dimethylbenzyl group, and a phenylethyl group.

[0219] R in formula (1) １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４Examples of the heterocyclic group having 2 to 20 carbon atoms represented by the formula (I) include a pyridyl group, a pyrimidyl group, a furyl group, a thienyl group, a tetrahydrofuryl group, a dioxolanyl group, a benzoxazol-2-yl group, a tetrahydropyranyl group, a pyrrolidyl group, an imidazolidyl group, a pyrazolidyl group, a thiazolidyl group, an isothiazolidyl group, an oxazolidyl group, an isoxazolidyl group, a piperidyl group, a piperazyl group, and a morpholinyl group, and are preferably 5- to 7-membered heterocyclic rings.

[0220] R in formula (1) １２ and R １３ and R ２２ and R ２３ may be joined together to form a ring, １２ and R １３ and R ２２ and R ２３ means that they may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are attached.

[0221] R in formula (1) １２ and R １３ and R ２２ and R ２３ Examples of the ring that can be formed by combining these include a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a benzene ring, a piperidine ring, a morpholine ring, a lactone ring, and a lactam ring, and preferably a 5- to 7-membered ring.

[0222] R in formula (1) １１ , R １２ , R １３ , R ２１ , R ２２ and R ２３ Examples of the halogen atom which may be contained as a substituent include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0223] R in formula (1) １ is preferably R １１ and more preferably an alkyl group having 1 to 20 carbon atoms, even more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms.

[0224] An example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by the following formula (2): The second molecular structure means a molecular structure portion other than the first molecular structure possessed by the oxime compound (1).

[0225] The bond represented by "*" in formula (2) is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (2), the benzene ring having "-*" in formula (2) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0226]

[0227] In formula (2), R ２ and R ３ are each independently R １１ , OR １１ , S.R. １１ , C.O.R. １１ , C.O.R. １２ R １３ , N.R. １２ COR １１ , O.C.O.R. １１ , COOR １１ , SCOR １１ , OCSR １１ , COSR １１ , CSOR １１ , CN or a halogen atom.

[0228] R ２ When there are multiple, they may be the same or different.

[0229] R ３ When there are multiple, they may be the same or different.

[0230] R １１ , R １２ and R １３ has the same meaning as above.

[0231] s and t each independently represent an integer of 0 to 4;

[0232] L is a sulfur atom, CR ３１ R ３２ , CO or NR ３３ Represents.

[0233] R ３１ , R ３２ and R ３３ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms.

[0234] R ３１ , R ３２ or R ３３ When the group represented by R ３１ , R ３２ and R ３３ may each independently combine with either adjacent benzene ring to form a ring.

[0235] R ４ represents a hydroxy group, a carboxy group, or a group represented by the following formula (2-1):

[0236]

[0237] (In formula (2-1), L １ is -O-, -S-, -NR ２２ -, -NR ２２ CO-, -SO ２ represents -, -CS-, -OCO- or -COO-.

[0238] R ２２ has the same meaning as above.

[0239] L ２ represents a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms, a group obtained by removing v hydrogen atoms from an aralkyl group having 7 to 30 carbon atoms, or a group obtained by removing v hydrogen atoms from a heterocyclic group having 2 to 20 carbon atoms.

[0240] L ２ has an alkylene moiety, the alkylene moiety is preferably —O—, —S—, —COO—, —OCO—, —NR ２２ -, -NR ２２ COO-,-OCONR ２２It may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-, and the alkylene moiety may be branched or cyclic.

[0241] R ４ａ is OR ４１ , S.R. ４１ , C.O.R. ４２ R ４３ , N.R. ４２ COR ４３ , O.C.O.R. ４１ , COOR ４１ , SCOR ４１ , OCSR ４１ , COSR ４１ , CSOR ４１ , CN or a halogen atom.

[0242] R ４ａ When there are multiple, they may be the same or different.

[0243] R ４１ , R ４２ and R ４３ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms; R ４１ , R ４２ and R ４３ When the group represented by R ４２ and R ４３ may be joined together to form a ring.

[0244] and v represents an integer of 1 to 3.

[0245] * represents a bond to the first molecular structure of the oxime compound (1).

[0246] R in formula (2) １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ , R ２４ , R ３１ , R ３２ and R ３３ , and R in the above formula (2-1)２２ , R ４１ , R ４２ and R ４３ Examples of the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, and the aralkyl group having 7 to 30 carbon atoms are represented by R １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４ The example is similar to that for

[0247] R in formula (2) １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ , R ２４ , and R in the above formula (2-1) ２２ Examples of the heterocyclic group having 2 to 20 carbon atoms represented by the formula (1) include R １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４ The example is similar to that for

[0248] R in formula (2) ３１ , R ３２ and R ３３ may each independently form a ring together with either adjacent benzene ring, ３１ , R ３２ and R ３３ means that each of the groups may independently combine with either of the adjacent benzene rings to form a ring together with the nitrogen atom to which it is connected.

[0249] R in formula (2) ３１ , R ３２ and R ３３ Examples of the ring that can be formed by combining with either adjacent benzene ring include R １２ and R １３ and R ２ and R ２３ The same is true for the rings that can be formed by combining the

[0250] L in the above formula (2-1) ２ represents a group in which v hydrogen atoms have been removed from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0251] Examples of the group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, when v is 1, include alkylene groups such as methylene, ethylene, propylene, methylethylene, butylene, 1-methylpropylene, 2-methylpropylene, 1,2-dimethylpropylene, 1,3-dimethylpropylene, 1-methylbutylene, 2-methylbutylene, 3-methylbutylene, 4-methylbutylene, 2,4-dimethylbutylene, 1,3-dimethylbutylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, dodecylene, tridecylene, tetradecylene, pentadecylene, ethane-1,1-diyl, and propane-2,2-diyl.

[0252] Examples of the group in which v hydrogen atoms have been removed from an aryl group having 6 to 30 carbon atoms, when v is 1, include arylene groups such as a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 2,6-naphthylene group, a 1,4-naphthylene group, a 2,5-dimethyl-1,4-phenylene group, a diphenylmethane-4,4'-diyl group, a 2,2-diphenylpropane-4,4'-diyl group, a diphenylsulfide-4,4'-diyl group, and a diphenylsulfone-4,4'-diyl group.

[0253] Examples of the group obtained by removing v hydrogen atoms from an aralkyl group having 7 to 30 carbon atoms, when v is 1, include a group represented by the following formula (a) and a group represented by the following formula (b):

[0254]

[0255] [In formulas (a) and (b), L ３ and L ５ represents an alkylene group having 1 to 10 carbon atoms, L ４ and L ６represents a single bond or an alkylene group having 1 to 10 carbon atoms.] Examples of the alkylene group having 1 to 10 carbon atoms include a methylene group, an ethylene group, a propylene group, a methylethylene group, a butylene group, a 1-methylpropylene group, a 2-methylpropylene group, a 1,2-dimethylpropylene group, a 1,3-dimethylpropylene group, a 1-methylbutylene group, a 2-methylbutylene group, a 3-methylbutylene group, a 4-methylbutylene group, a 2,4-dimethylbutylene group, a 1,3-dimethylbutylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, and a decylene group.

[0256] Examples of the group obtained by removing v hydrogen atoms from a heterocyclic group having 2 to 20 carbon atoms, when v is 1, include divalent heterocyclic groups such as a 2,5-pyridinediyl group, a 2,6-pyridinediyl group, a 2,5-pyrimidinediyl group, a 2,5-thiophenediyl group, a 3,4-tetrahydrofurandiyl group, a 2,5-tetrahydrofurandiyl group, a 2,5-furandiyl group, a 3,4-thiazolediyl group, a 2,5-benzofurandiyl group, a 2,5-benzothiophenediyl group, an N-methylindole-2,5-diyl group, a 2,5-benzothiazolediyl group, and a 2,5-benzoxazolediyl group.

[0257] R in formula (2) ２ and R ３ , and R in the above formula (2-1) ４ａ Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0258] From the viewpoint of solubility in the solvent (J) and / or developability of the curable composition, a preferred example of the structure represented by formula (2) is a structure represented by the following formula (2a).

[0259]

[0260] [In formula (2a), L′ represents a sulfur atom or NR ５０ represents R ５０ represents a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms; R ２ , R ３ , R ４, s and t have the same meanings as above.] From the same viewpoint as above, another preferable example of the structure represented by formula (2) is a structure represented by the following formula (2b).

[0261]

[0262] [In formula (2b), R ４４ represents a hydroxy group, a carboxy group, or a group represented by the following formula (2-2):

[0263]

[0264] (In formula (2-2), L １１ represents *-O- or *-OCO-, and * represents L １２ represents a bond with L １２ represents an alkylene group having 1 to 20 carbon atoms, and the alkylene group may be interrupted by 1 to 3 —O— groups; ４４ａ is OR ５５ or COOR ５５ represents R ５５ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ４４ is preferably a group represented by formula (2-2), which is advantageous in terms of the solubility of the oxime compound (1) in the solvent (J) and the developability of the curable composition.

[0265] L １２ The alkylene group represented by the formula (I) preferably has 1 to 10 carbon atoms, and more preferably has 1 to 4 carbon atoms.

[0266] R ４４ａ is preferably a hydroxy group or a carboxy group, more preferably a hydroxy group.

[0267] The method for producing the oxime compound (1) having the second molecular structure represented by formula (2) is not particularly limited, but it can be produced, for example, by the method described in JP-A-2011-132215.

[0268] Another example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by formula (3) below.

[0269] The bond represented by "*" in formula (3) is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (3), the benzene ring having "-*" in formula (3) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0270]

[0271] In formula (3), R ５ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0272] R ５ When the group represented by the formula (I) has an alkyl moiety, the alkyl moiety may be branched or cyclic.

[0273] R ５ The hydrogen atoms of the group represented by R ２１ , OR ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , N.R. ２２ COR ２１ , O.C.O.R. ２１ , COOR ２１ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , SCOR ２１ , OCSR ２１ , COSR ２１ , CSOR ２１ , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR ２１ may be substituted with.

[0274] R ２１ , R ２２ and R ２３ has the same meaning as above.

[0275] R ２１ , R ２２ or R ２３ The hydrogen atom of the group represented by the formula (I) may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.

[0276] R ２１ , R ２２ and R ２３ has an alkylene moiety, the alkylene moiety is preferably —O—, —S—, —COO—, —OCO—, —NR ２４ -, -NR ２４ CO-, -NR ２４ COO-,-OCONR ２４ It may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-.

[0277] R ２４ has the same meaning as above.

[0278] R ２１ , R ２２ and R ２３ When the group represented by R ２２ and R ２３ may be joined together to form a ring.

[0279] R ６ , R ７ , R ８ and R ９ are each independently R ６１ , OR ６１ , S.R. ６１ , C.O.R. ６２ , C.O.R. ６３ R ６４ , N.R. ６５ COR ６１ , O.C.O.R. ６１ , COOR ６２ , SCOR ６１ , OCSR ６１ , COSR ６２ , CSOR ６１ , a hydroxyl group, a nitro group, CN or a halogen atom.

[0280] R ６１ , R ６２ , R６３ , R ６４ and R ６５ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0281] R ６１ , R ６２ , R ６３ , R ６４ or R ６５ The hydrogen atom of the group represented by ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , CN, a halogen atom, or COOR ２１ may be substituted with.

[0282] R ６ and R ７ , R ７ and R ８ and R ８ and R ９ may be joined together to form a ring.

[0283] * represents a bond to the first molecular structure of the oxime compound (1).

[0284] R in formula (3) ５ , R ２１ , R ２２ , R ２３ , R ２４ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms, which are represented by the formula (1), are R１１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４ The example is similar to that for

[0285] R in formula (3) ２２ and R ２３ may be taken together to form a ring, ２２ and R ２３ means that they may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are attached.

[0286] R in formula (3) ２２ and R ２３ Examples of rings that can be formed by combining are R １２ and R １３ and R ２２ and R ２３ The same is true for the rings that can be formed by combining the

[0287] R in formula (3) ６ , R ７ , R ８ and R ９ a halogen atom represented by R ５ , R ２１ , R ２２ , R ２３ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of halogen atoms which may replace the hydrogen atoms include fluorine, chlorine, bromine and iodine atoms.

[0288] In one preferred embodiment, from the viewpoint of solubility in the solvent (J) and / or developability of the curable composition, R ５ is a group represented by the following formula (3-1).

[0289]

[0290] [In formula (3-1), Z represents a group in which one hydrogen atom has been removed from an alkyl group having 1 to 20 carbon atoms, a group in which one hydrogen atom has been removed from an aryl group having 6 to 30 carbon atoms, a group in which one hydrogen atom has been removed from an aralkyl group having 7 to 30 carbon atoms, or a group in which one hydrogen atom has been removed from a heterocyclic group having 2 to 20 carbon atoms, and when the group represented by Z has an alkylene moiety, the alkylene moiety is selected from the group consisting of -O-, -S-, -COO-, -OCO-, -NR ２４ -, -NR ２４ COO-,-OCONR ２４ may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-, and the alkylene moiety may be branched or cyclic; R ２１ , R ２２ and R ２４ has the same meaning as defined above.] From the same viewpoint as above, Z in formula (3-1) is preferably a methylene group, an ethylene group, or a phenylene group.

[0291] R in formula (3-1) ２１ and R ２２ From the same viewpoint as above, is preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, and more preferably a methyl group, an ethyl group, or a phenyl group.

[0292] From the same viewpoint as above, in another preferred embodiment, R ７ is a nitro group.

[0293] The method for producing the oxime compound (1) having the second molecular structure represented by formula (3) is not particularly limited, but it can be produced by, for example, the methods described in JP-A-2000-80068 and JP-A-2011-178776.

[0294] Yet another example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by formula (4) below.

[0295] The bond represented by "*" in formula (4) is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (4), the benzene ring having "-*" in formula (4) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0296]

[0297] In formula (4), R ７１ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0298] R ７１ When the group represented by the formula (I) has an alkyl moiety, the alkyl moiety may be branched or cyclic.

[0299] R ７１ The hydrogen atoms of the group represented by R ２１ , OR ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , N.R. ２２ COR ２１ , O.C.O.R. ２１ , COOR ２１ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , SCOR ２１ , OCSR ２１ , COSR ２１ , CSOR ２１ , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR ２１ may be substituted with.

[0300] R ２１ , R ２２ and R ２３ represents the same meaning as above.

[0301] R ２１ , R ２２ or R ２３ The hydrogen atom of the group represented by the formula (I) may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.

[0302] R ２１ , R ２２ and R ２３ has an alkylene moiety, the alkylene moiety is preferably —O—, —S—, —COO—, —OCO—, —NR ２４ -, -NR ２４ CO-, -NR ２４ COO-,-OCONR ２４ It may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-.

[0303] R ２４ has the same meaning as above.

[0304] R ２１ , R ２２ and R ２３ When the group represented by R ２２ and R ２３ may be joined together to form a ring.

[0305] R ７２ , R ７３ and three R ７４ are each independently R ６１ , OR ６１ , S.R. ６１ , C.O.R. ６２ , C.O.R. ６３ R ６４ , N.R. ６５ COR ６１ , O.C.O.R. ６１ , COOR ６２ , SCOR ６１ , OCSR ６１ , COSR ６２ , CSOR ６１ , a hydroxyl group, a nitro group, CN or a halogen atom.

[0306] R ６１ , R ６２ , R ６３, R ６４ and R ６５ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0307] R ６１ , R ６２ , R ６３ , R ６４ or R ６５ The hydrogen atom of the group represented by ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , CN, a halogen atom, or COOR ２１ may be substituted with.

[0308] R ７２ and R ７３ and two R ７４ may be joined together to form a ring.

[0309] * represents a bond to the first molecular structure of the oxime compound (1).

[0310] R in formula (4) ７１ , R ２１ , R ２２ , R ２３ , R ２４ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms, which are represented by the formula (1), are R １１ , R １２ , R １３ , R ２１, R ２２ , R ２３ and R ２４ The example is similar to that for

[0311] R in formula (4) ２２ and R ２３ may be taken together to form a ring, ２２ and R ２３ means that they may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are attached.

[0312] R in formula (4) ２２ and R ２３ Examples of rings that can be formed by combining are R １２ and R １３ and R ２２ and R ２３ The same is true for the rings that can be formed by combining the

[0313] R in formula (4) ７２ , R ７３ and R ７４ a halogen atom represented by R ７１ , R ２１ , R ２２ , R ２３ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of halogen atoms which may replace the hydrogen atoms include fluorine, chlorine, bromine and iodine atoms.

[0314] The method for producing the oxime compound (1) having the second molecular structure represented by formula (4) is not particularly limited, and the compound can be produced, for example, by the methods described in WO 2017 / 051680 and WO 2020 / 004601.

[0315] Yet another example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by formula (5) below.

[0316] The bond represented by "*" in formula (5) is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (5), the pyrrole ring having "-*" in formula (5) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0317]

[0318] In formula (5), R ８１ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0319] R ８１ When the group represented by the formula (I) has an alkyl moiety, the alkyl moiety may be branched or cyclic.

[0320] R ８１ The hydrogen atoms of the group represented by R ２１ , OR ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , N.R. ２２ COR ２１ , O.C.O.R. ２１ , COOR ２１ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , SCOR ２１ , OCSR ２１ , COSR ２１ , CSOR ２１ , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR ２１ may be substituted with.

[0321] R ２１ , R ２２ and R ２３ has the same meaning as above.

[0322] R ２１ , R ２２ or R ２３ The hydrogen atom of the group represented by the formula (I) may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.

[0323] R ２１ , R ２２ and R ２３ has an alkylene moiety, the alkylene moiety is preferably —O—, —S—, —COO—, —OCO—, —NR ２４ -, -NR ２４ CO-, -NR ２４ COO-,-OCONR ２４ It may be interrupted 1 to 5 times by -, -SCO-, -COS-, -OCS- or -CSO-.

[0324] R ２４ has the same meaning as above.

[0325] R ２１ , R ２２ and R ２３ When the group represented by R ２２ and R ２３ may be joined together to form a ring.

[0326] R ８２ , R ８３ , R ８４ , R ８５ and R ８６ are each independently R ６１ , OR ６１ , S.R. ６１ , C.O.R. ６２ , C.O.R. ６３ R ６４ , N.R. ６５ COR ６１ , O.C.O.R. ６１ , COOR ６２ , SCOR ６１ , OCSR ６１ , COSR ６２ , CSOR ６１ , a hydroxyl group, a nitro group, CN or a halogen atom.

[0327] R ６１ , R６２ , R ６３ , R ６４ and R ６５ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0328] R ６１ , R ６２ , R ６３ , R ６４ or R ６５ The hydrogen atom of the group represented by ２１ , C.O.R. ２１ , S.R. ２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , CN, a halogen atom, or COOR ２１ may be substituted with.

[0329] R ８３ and R ８４ , R ８４ and R ８５ and R ８５ and R ８６ may be joined together to form a ring.

[0330] * represents a bond to the first molecular structure of the oxime compound (1).

[0331] R in formula (5) ８１ , R ２１ , R ２２ , R ２３ , R ２４ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５Examples of the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms, which are represented by the formula (1), are R １１ , R １２ , R １３ , R ２１ , R ２２ , R ２３ and R ２４ The example is similar to that for

[0332] R in formula (5) ２２ and R ２３ may be taken together to form a ring, ２２ and R ２３ means that they may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are attached.

[0333] R in formula (5) ２２ and R ２３ Examples of rings that can be formed by combining are R １２ and R １３ and R ２２ and R ２３ The same is true for the rings that can be formed by combining the

[0334] R in formula (5) ８２ , R ８３ , R ８４ , R ８５ and R ８６ a halogen atom represented by R ８１ , R ２１ , R ２２ , R ２３ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of halogen atoms which may replace the hydrogen atoms include fluorine, chlorine, bromine and iodine atoms.

[0335] The method for producing the oxime compound (1) having the second molecular structure represented by formula (5) is not particularly limited, and the compound can be produced, for example, by the methods described in WO 2017 / 051680 and WO 2020 / 004601.

[0336] Yet another example of the second molecular structure linked to the first molecular structure represented by formula (1) is a structure represented by formula (6) below.

[0337] The bond represented by "*" in formula (6) is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (6), the benzene ring having "-*" in formula (6) and the carbonyl group having "-*" in formula (1) are directly bonded.

[0338]

[0339] In formula (6), four R ９１ , R ９２ , R ９３ , R ９４ , R ９５ , R ９６ and R ９７ are each independently R ６１ , OR ６１ , S.R. ６１ , C.O.R. ６２ , C.O.R. ６３ R ６４ , N.R. ６５ COR ６１ , O.C.O.R. ６１ , COOR ６２ , SCOR ６１ , OCSR ６１ , COSR ６２ , CSOR ６１ , a hydroxyl group, a nitro group, CN or a halogen atom.

[0340] R ６１ , R ６２ , R ６３ , R ６４ and R ６５ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

[0341] R ６１ , R ６２ , R ６３ , R ６４ or R ６５ The hydrogen atom of the group represented by ２１ , C.O.R. ２１ , S.R.２１ , N.R. ２２ R ２３ , C.O.R. ２２ R ２３ , -NR ２２ -OR ２３ , -N(COR ２２ )-OCOR ２３ , -C(=N-OR ２１ )-R ２２ , -C(=N-OCOR ２１ )-R ２２ , CN, a halogen atom, or COOR ２１ may be substituted with.

[0342] R ２１ , R ２２ and R ２３ has the same meaning as above.

[0343] R ９２ and R ９３ , R ９４ and R ９５ , R ９５ and R ９６ and R ９６ and R ９７ may be joined together to form a ring.

[0344] * represents a bond to the first molecular structure of the oxime compound (1).

[0345] R in formula (6) ２１ , R ２２ , R ２３ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms, which are represented by the formula (1), are R １１ , R １２ , R １３ , R ２１ , R ２２ and R ２３ The example is similar to that for

[0346] R in formula (6) ２２ and R ２３ may be taken together to form a ring,２２ and R ２３ means that they may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are attached.

[0347] R in formula (6) ２２ and R ２３ Examples of rings that can be formed by combining are R １２ and R １３ and R ２２ and R ２３ The same is true for the rings that can be formed by combining the

[0348] R in formula (6) ９１ , R ９２ , R ９３ , R ９４ , R ９５ , R ９６ and R ９７ a halogen atom represented by R ２１ , R ２２ , R ２３ , R ６１ , R ６２ , R ６３ , R ６４ and R ６５ Examples of halogen atoms which may replace the hydrogen atoms include fluorine, chlorine, bromine and iodine atoms.

[0349] The method for producing the oxime compound (1) having the second molecular structure represented by formula (6) is not particularly limited, and the compound can be produced, for example, by the methods described in WO 2017 / 051680 and WO 2020 / 004601.

[0350] Examples of oxime compounds other than the compounds represented by formula (EA), the compounds represented by formula (EB), and the oxime compound (1) include oxime compounds having a partial structure represented by the following formula (d1), in which * represents a bond.

[0351]

[0352] Examples of oxime compounds having a partial structure represented by formula (d1) include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl -2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine; and compounds described in JP 2011-132215 A, WO 2008 / 78678, WO 2008 / 78686, and WO 2012 / 132558. Commercially available products such as Irgacure OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine), OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine) (all manufactured by BASF), and N-1919 (manufactured by ADEKA) may also be used.

[0353] Among these, the oxime compound having a partial structure represented by formula (d1) is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine or N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine.

[0354] The alkylphenone compound is a compound having a partial structure represented by the following formula (d2) or a partial structure represented by the following formula (d3). In these partial structures, the benzene ring may have a substituent. * represents a bond.

[0355]

[0356] Examples of compounds having a structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as OMNIRAD (registered trademark) 369, 907, and 379 (all manufactured by IGM Resins) may also be used.

[0357] Examples of the compound having a structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0358] In terms of sensitivity, the alkylphenone compound is preferably a compound having a structure represented by formula (d2).

[0359] An example of the biimidazole compound is a compound represented by formula (d5).

[0360]

[0361] [In formula (d5), R Ｅ ~R Ｊ represents an aryl group having 6 to 10 carbon atoms which may have a substituent.] Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a toluyl group, a xylyl group, an ethylphenyl group, and a naphthyl group, and a phenyl group is preferred.

[0362] Examples of the substituent include a halogen atom and an alkoxy group having 1 to 4 carbon atoms. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, with a methoxy group being preferred.

[0363] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A Nos. 06-75372 and 06-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) Examples of suitable biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913). Among these, compounds represented by the following formula or mixtures thereof are preferred:

[0364]

[0365] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, etc. Among these, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine is preferred.

[0366] Examples of the acylphosphine compound include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide.

[0367] Other examples of the photopolymerization initiator include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, and 4,4'-bis(diethylamino)benzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, and titanocene compounds.

[0368] The content of the polymerization initiator (E) in the curable composition is preferably 0.1 parts by mass or more and 300 parts by mass or less, more preferably 0.1 parts by mass or more and 200 parts by mass or less, even more preferably 3 parts by mass or more and 150 parts by mass or less, and even more preferably 5 parts by mass or more and 80 parts by mass or less, relative to 100 parts by mass of the polymerizable compound (D). Furthermore, the content of the polymerization initiator (E) in the curable composition is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 0.5 parts by mass or more and 20 parts by mass or less, and even more preferably 1 part by mass or more and 10 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (C) and the polymerizable compound (D). When the content of the polymerization initiator (E) is within the above range, a decrease in the residual film rate of the cured film when the curable composition is cured at low temperature can be suppressed, and it is also advantageous from the viewpoint of improving patterning after exposure and development.

[0369] The content of the polymerization initiator (E) in the curable composition is, for example, 0.01 mass% or more and 20 mass% or less, preferably 0.1 mass% or more and 15 mass% or less, more preferably 0.2 mass% or more and 10 mass% or less, even more preferably 0.3 mass% or more and 8 mass% or less, still more preferably 0.5 mass% or more and 5 mass% or less, and particularly preferably 3 mass% or less, relative to the total amount of solids in the curable composition.

[0370] The polymerization initiator (E) preferably contains at least one oxime compound, more preferably contains at least one of the compounds represented by formula (EA), formula (EB), and oxime compound (1), even more preferably contains at least one of the compounds represented by formula (EA) and formula (EB), still more preferably contains at least one of the compounds represented by formula (EA), and even more preferably contains a compound represented by formula (EA-1) described below. As described above, both the compound represented by formula (EA) and the compound represented by formula (EB) can suppress a decrease in the residual film rate of the cured film when the curable composition is cured at low temperature. Furthermore, the compound represented by formula (EA) can further improve the fluorescence emission intensity of the cured film. The content of the compound represented by formula (EA) is preferably 50% by mass or more, more preferably 80% by mass or more, and even more preferably 100% by mass (i.e., the polymerization initiator (E) contains the compound represented by formula (EA) and does not contain the compound represented by formula (EB)), relative to 100% by mass of the total amount of the compound represented by formula (EA) and the compound represented by formula (EB)).

[0371] When the polymerization initiator (E) contains at least one of the compound represented by formula (EA) and the compound represented by formula (EB), the total content of the compound represented by formula (EA) and the compound represented by formula (EB) in the polymerization initiator (E) is preferably 30% by mass or more and 100% by mass or less, more preferably 50% by mass or more and 100% by mass or less, even more preferably 70% by mass or more and 100% by mass or less, still more preferably 80% by mass or more and 100% by mass or less, especially preferably 90% by mass or more and 100% by mass or less, and particularly preferably 95% by mass or more and 100% by mass or less, and may be 100% by mass, based on the total amount of the polymerization initiator (E).

[0372] <Light Stabilizer (F)> The light stabilizer (F) includes known light stabilizers (Fa), as well as any additive that has the effect of stabilizing components against light. The light stabilizer (F) of the present invention also includes an antioxidant (Fb) and an ultraviolet absorber (Fc) that absorbs light and renders it harmless. The curable composition may contain two or more light stabilizers (F).

[0373] <Light Stabilizer (Fa)> Examples of the light stabilizer (Fa) include hindered amine light stabilizers, acrylate light stabilizers, nickel light stabilizers, and oxamide light stabilizers.

[0374] <Antioxidant (Fb)> The antioxidant (Fb) is not particularly limited as long as it is an antioxidant commonly used industrially, and examples thereof include phenol-based antioxidants, phosphorus-based antioxidants, phosphorus / phenol complex antioxidants, and sulfur-based antioxidants. The curable composition may contain two or more types of antioxidants (Fb).

[0375] The phosphorus / phenol complex antioxidant is, for example, a compound having one or more phosphorus atoms and one or more phenol structures in the molecule. Among these, from the viewpoints of the developability and luminescence intensity of the curable composition, it is preferable that the antioxidant (Fb) contains a phosphorus / phenol complex antioxidant.

[0376] Examples of phenolic antioxidants include Irganox (registered trademark) 1010 (Irganox 1010: pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF Corporation), Irganox 1330 (Irganox 1330: 3,3',3'',5,5',5''-hexa-tert-butyl-a,a',a''-(mesitylene-2,4,6-triyl)tri-p-cresol, manufactured by BASF Corporation), and Irganox 3114 (Irganox 1330: 3,3',3'',5,5',5''-hexa-tert-butyl-a,a',a''-(mesitylene-2,4,6-triyl)tri-p-cresol, manufactured by BASF Corporation). 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation, Irganox 3790 (Irganox 3790): 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation, Irganox 1035 (Irganox 1035): thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), Irganox 1135 (Irganox Irganox 1135: 3,5-bis(1,1-dimethylethyl)-4-hydroxy-C7-C9 side chain alkyl ester of benzenepropanoic acid, manufactured by BASF Corporation; Irganox 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Corporation); Irganox 3125 (Irganox 3125, manufactured by BASF Corporation); Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy-3',5'-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF Corporation); Adekastab (registered trademark) AO-80 (Adekastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5) Undecane (manufactured by ADEKA Corporation), Sumilizer (registered trademark) BHT, Sumilizer GA-80, Sumilizer GS (all manufactured by Sumitomo Chemical Co., Ltd.), Cyanox (registered trademark) 1790 (manufactured by Cytec Co., Ltd.), Vitamin E (manufactured by Eisai Co., Ltd.), etc.

[0377] Examples of phosphorus-based antioxidants include Irgafos (registered trademark) 168 (Irgafos 168: tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF Corporation), Irgafos 12 (Irgafos 12: tris[2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl]oxy]ethyl]amine, manufactured by BASF Corporation), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Corporation), Adekastab (registered trademark) 329K, Adekastab PEP36, Adekastab PEP-8 (all manufactured by ADEKA Corporation), and Sandstab Examples of such an anti-fouling agent include P-EPQ (manufactured by Clariant), Weston (registered trademark) 618 and 619G (all manufactured by GE), and Ultranox 626 (manufactured by GE).

[0378] Examples of phosphorus / phenol complex antioxidants include Sumilizer (registered trademark) GP (6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphosphepine) (manufactured by Sumitomo Chemical Co., Ltd.).

[0379] Examples of sulfur-based antioxidants include dialkyl thiodipropionate compounds such as dilauryl, dimyristyl, and distearyl thiodipropionate, and β-alkylmercaptopropionic acid ester compounds of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane.

[0380] <Ultraviolet Absorber (Fc)> Examples of the ultraviolet absorber (Fc) include benzotriazole compounds such as 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole and (2-(2,4-dihydroxyphenyl)-2H-benzotriazole); benzophenone compounds such as 2-hydroxy-4-octyloxybenzophenone; benzoate compounds such as 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate; and triazine compounds such as 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexyloxyphenol.

[0381] The content of the light stabilizer (F) in the curable composition (the total amount when there are multiple types) is, for example, 1 part by mass or more and 50 parts by mass or less relative to 100 parts by mass of the resin (C), and from the viewpoint of luminescence intensity, it is preferably 5 parts by mass or more and 40 parts by mass or less, and more preferably 7 parts by mass or more and 30 parts by mass or less.

[0382] When the curable composition contains a light stabilizer (F), the light stabilizer (F) is preferably an antioxidant (Fb) and / or an ultraviolet absorber (Fc).

[0383] <Leveling Agent (H)> Examples of the leveling agent (H) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain. The leveling agent (H) preferably contains a silicone surfactant. The curable composition may contain two or more types of leveling agents (H).

[0384] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule.Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0385] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorard (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, F575, R30, and RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Ltd.).

[0386] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0387] When the curable composition contains a leveling agent (H), the content of the leveling agent (H) in the curable composition is, for example, 0.001 mass% or more and 1.0 mass% or less, preferably 0.005 mass% or more and 0.75 mass% or less, and more preferably 0.01 mass% or more and 0.5 mass% or less, relative to the total amount of the curable composition. When the content of the leveling agent (H) is within the above range, the flatness of a cured film of the curable composition when used as a wavelength conversion layer can be improved.

[0388] <Solvent (J)> The solvent (J) dissolves the resin (C), and the polymerizable compound (D) and polymerization initiator (E) used in a preferred embodiment. Examples of the solvent (J) include ester solvents (solvents containing —COO— but not —O— in the molecule), ether solvents (solvents containing —O— but not —COO— in the molecule), ether ester solvents (solvents containing —COO— and —O— in the molecule), ketone solvents (solvents containing —CO— but not —COO— in the molecule), alcohol solvents (solvents containing OH in the molecule and not containing —O—, —CO—, and COO—), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0389] Examples of the ester solvent include methyl lactate, ethyl lactate, n-butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, isopropyl butyrate, ethyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate, and γ-butyrolactone.

[0390] 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, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0391] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methyl ... Examples of the alkyl ether acetate include ethyl 2-methoxypropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0392] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0393] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0394] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0395] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0396] The solvent (J) preferably contains one or more solvents selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, cyclohexyl acetate, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and aromatic hydrocarbon solvents.

[0397] The solvent (J) is preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, cyclohexyl acetate, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, toluene, or a mixture of two or more of these.

[0398] The solvent (J) is a component other than the solid content, and includes, for example, solvents contained in the dispersion of the semiconductor particles (A) and the solution of the resin (C).

[0399] The content of solvent (J) in the curable composition is the ratio of the total mass of all solvents contained in the curable composition to the total amount of the curable composition, and is, for example, 40% by mass or more and 95% by mass or less, and preferably 50% by mass or more and 90% by mass or less, relative to the total amount of the curable composition. In other words, the solid content of the curable composition is, for example, 5% by mass or more and 60% by mass or less, and preferably 10% by mass or more and 50% by mass or less. When the content of solvent (J) is within the above range, the flatness of the curable composition layer during application is improved, and a wavelength conversion layer with an appropriate thickness tends to be easily formed.

[0400] <Other Components> The curable composition may further contain additives known in the technical field, such as a polymerization inhibitor, a filler, another polymer compound, an adhesion promoter, or a chain transfer agent, as needed.

[0401] <<Method for Producing Curable Composition>> The curable composition can be produced by a method including a step of mixing predetermined components and other components used as needed. The method for producing the curable composition can further include a step of preparing a resin (C). Of the components contained in the curable composition, the semiconductor particles (A) and the light scattering agent (B) may be mixed in advance with a part or all of the solvent (J) and then mixed with the other components.

[0402] <<Method for Producing Cured Film>> A cured film can be obtained by carrying out a production method including a step of applying the curable composition of the present invention and a heat curing step of thermally curing the coated film of the curable composition (hereinafter also referred to as "composition layer"). After the step of applying the curable composition, the method usually further includes an exposure step of irradiating the coated film of the curable composition with light, and the heat curing step is carried out after the exposure step.

[0403] The method for producing the cured film described above further includes a drying step of drying the composition layer formed in the coating step, and a development step of carrying out on the composition layer after the exposure step.

[0404] The coating step is a step of coating a curable composition onto a substrate to form a composition layer. Examples of coating methods include spin coating, slit coating, slit and spin coating, and printing. In the printing method, the curable composition is coated on a substrate through a mask, and after peeling the mask from the substrate, the composition layer formed in the coating step is cured, thereby forming a cured film as a cured pattern on a part of the substrate surface.

[0405] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and the above substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed, etc. The substrate is preferably a glass plate or a silicon substrate.

[0406] The substrate may be subjected to a pretreatment capable of adjusting the wettability of the substrate surface. Examples of the pretreatment include washing with a solvent such as alcohol or acetone, acid treatment, alkali treatment, plasma treatment, and corona treatment. By selecting an appropriate pretreatment for the substrate on which a cured film is to be laminated, the coatability of the curable composition can be improved compared to an untreated substrate.

[0407] When the curable composition contains a solvent (J), the coating step is followed by a drying step in which volatile components such as the solvent (J) are removed from the composition layer. The drying step may include a heat drying (pre-baking) treatment, a reduced pressure drying treatment, or both.

[0408] The curable composition of the present invention can suppress a decrease in the residual film rate of the cured film when the heat drying (pre-bake) temperature is set low. The temperature when heat drying is performed is preferably 30°C or higher but lower than 100°C, and more preferably 50°C or higher but 95°C or lower. The heating time is preferably 10 seconds or higher but 60 minutes or lower, and more preferably 30 seconds or higher but 30 minutes or lower. When drying under reduced pressure is performed, it is preferably performed under a pressure of 50 Pa or higher but 150 Pa or lower and at a temperature range of 20°C or higher but 25°C or lower.

[0409] The film thickness of the composition layer after the coating step or the drying step is not particularly limited and may be appropriately selected depending on the film thickness of the desired cured film, and is, for example, 0.5 μm or more and 10 μm or less, preferably 1 μm or more and 9 μm or less, more preferably 1.5 μm or more and 7 μm or less, and even more preferably 2 μm or more and 5 μm or less. The film thickness of the finally obtained cured film may also be the same as above.

[0410] Next, an exposure step is carried out on the composition layer after the coating step and the drying step. The exposed composition layer is cured by polymerization of the polymerizable compound (D) and the like contained in the composition layer, including preferred embodiments. The light source used for exposure is preferably a light source that generates light with a wavelength of 250 nm or more and 450 nm or less. When the curable composition contains a photopolymerization initiator (E), light with a wavelength of around 436 nm, around 408 nm, or around 365 nm may be selectively extracted using a bandpass filter from the light with the above wavelengths, depending on the absorption wavelength of the polymerization initiator (E). Specific examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0411] The exposure dose X in the exposure step is preferably 50 mJ / cm ２ More preferably, 80 mJ / cm ２ More preferably, 100 mJ / cm ２ More preferably, 150 mJ / cm ２ The exposure dose X is usually 1000 mJ / cm ２ or less, preferably 800 mJ / cm ２ or less, more preferably 700 mJ / cm ２ The exposure dose X in the exposure step is 1000 mJ / cm or less. ２ When the exposure dose X is less than 1000 ppm, the cured film can be prevented from shrinking too much, and therefore the semiconductor particles (A) can be prevented from coming into close proximity in the film due to shrinkage of the cured film, thereby preventing a decrease in the intensity of emitted light. The exposure dose X is the exposure dose based on a wavelength of 365 nm, and can be measured using an ultraviolet integrating actinometer (UIT-250, manufactured by Ushio Inc.).

[0412] Photolithography is an example of a method for forming a cured pattern, which is one aspect of a cured film. Photolithography is a method in which a composition layer is exposed to light through a photomask for forming a desired cured pattern, followed by development. In this case, it is preferable to use an exposure device such as a mask aligner or a stepper, because this allows uniform irradiation of parallel light rays over the entire exposure surface and allows accurate alignment between the photomask and the substrate on which the composition layer is formed.

[0413] By subjecting the composition layer after the exposure step to a development step in which the layer is developed by contacting it with a developer, the unexposed portions of the composition layer are dissolved and removed in the developer, thereby forming a pattern on the composition layer. Examples of the developer include aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide, and organic solvents. The concentration of the alkaline 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. Examples of the organic solvent include those similar to the solvent (J) described above. The developer may contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, and the like. Furthermore, the substrate may be tilted at any angle during development.

[0414] The composition layer after the exposure step and the development step is thermally cured (post-baked) in a thermal curing step, which allows the polymerization of the resin (C), the polymerizable compound (D), and the like, including preferred embodiments, to proceed further.

[0415] The heat curing temperature in the heat curing step carried out after the exposure step and the development step is preferably 150° C. or lower, more preferably 120° C. or lower, even more preferably lower than 100° C., and particularly preferably 95° C. or lower. The heat curing temperature is preferably 70° C. or higher, more preferably 80° C. or higher, and even more preferably 85° C. or higher.

[0416] The heat curing time in the heat curing step is preferably 0.1 hour or more, more preferably 0.2 hour or more, even more preferably 0.4 hour or more, and still more preferably 0.5 hour or more. The heat curing time is usually 2 hours or less, preferably 1.5 hours or less, and more preferably 1.2 hours or less.

[0417] The thermal curing step can be carried out in air or in a vacuum atmosphere, where the pressure is 150 Pa or less, preferably 120 Pa or less, more preferably 100 Pa or less, and may be 50 Pa or more.

[0418] The temperatures in the drying step (particularly heat drying) and the heat curing step are preferably both less than 100°C, and more preferably 95°C or lower.

[0419] When a cured film produced at the above-mentioned preferred heat drying (pre-bake) temperature, or a cured film produced at the above-mentioned preferred heat drying temperature and heat curing temperature, is measured according to "Measurement of film retention rate" in the Examples described later, the film retention rate (film retention rate at low temperature curing) is, for example, more than 75%, preferably 80% or more, more preferably 90% or more, and the upper limit may be 100%. Furthermore, when the cured film is evaluated according to "Evaluation of patterning ability" in the Examples described later, the minimum line width at which the exposed pattern remains partially or completely can be 30 μm or less, more preferably 20 μm or less, and even more preferably 10 μm or less. Furthermore, when the cured film is evaluated according to "Measurement of fluorescence emission intensity of cured film" in the Examples described later, the emission intensity is 400 (mW·sr ―１ ・m ―２ ) or more, and ―１ ・m ―２ ) or more, and 700 (mW·sr ―１ ・m ―２ ) or more, and the upper limit is not particularly limited, but is 1500 (mW·sr ―１ ・m ―２ ) or less.

[0420] <<Display Device>> A cured film obtained from the curable composition of the present invention has the function of converting the wavelength of irradiated light, and can therefore be used as a color conversion layer (wavelength conversion film) in a display device. Examples of such a display device include those described in JP 2006-309219 A, JP 2006-310303 A, JP 2013-15812 A, JP 2009-251129 A, and JP 2014-2363 A. The cured film of the present invention is useful as a color conversion layer (wavelength conversion film) in a display device, particularly a liquid crystal display device, an organic EL display device, or an inorganic EL display device.

[0421] The present invention will be described in more detail below with reference to examples. The present invention is not limited to the following examples, and can of course be practiced with appropriate modifications within the scope of the above-mentioned and below-mentioned aims, all of which are included in the technical scope of the present invention. "%" and "parts" in the examples are by mass % and parts by mass unless otherwise specified.

[0422] [Thickness of Cured Film] The thickness was measured using a film thickness measuring device (DEKTAKXT, manufactured by Bruker).

[0423] [Weight-average molecular weight] The weight-average molecular weight (Mw) of resin (C) was measured by GPC under the following conditions: Apparatus: K2479 (Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI Calibration standard: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Tosoh Corporation)

[0424] [Acid Value] 3 g of the resin (C) solution was precisely weighed and dissolved in a mixed solvent of 90 g of acetone and 10 g of water. Using a 0.1 N KOH aqueous solution as a titrant, the acid value of the resin (C) solution was measured with an automatic titrator (manufactured by Hiranuma Sangyo Co., Ltd., product name: COM-555). The acid value (AV) per 1 g of solid content was calculated from the acid value of the solution and the solid content of the solution.

[0425] [Double Bond Equivalent] The double bond equivalent was determined by dividing the total mass of the curable resin by the number of moles of the radically polymerizable double bonds introduced into the curable resin.

[0426] [Solid content] Approximately 1 g of the resin (C) solution was weighed into an aluminum cup, dried at 180° C. for 1 hour, and then the mass was measured. The solid content (% by mass) of the resin (C) solution was calculated from the amount of mass loss.

[0427] Synthesis Example 1: Synthesis of Resin (C1) 276.8 g of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 120°C. Next, a monomer mixture consisting of 92.4 g of 2-ethylhexyl acrylate, 184.9 g of glycidyl methacrylate, and 12.3 g of dicyclopentanyl methacrylate, to which 35.3 g of t-butylperoxy-2-ethylhexanoate (polymerization initiator) had been added, was added dropwise from the dropping funnel to the flask over 2 hours. After completion of the dropwise addition, the mixture was stirred at 120°C for an additional 30 minutes to carry out a copolymerization reaction, thereby producing an addition copolymer.

[0428] Thereafter, the atmosphere in the flask was replaced with air, and 93.7 g of acrylic acid, 1.5 g of triphenylphosphine (catalyst) and 0.8 g of methoquinone (polymerization inhibitor) were added to the addition copolymer solution, and the reaction was continued for 10 hours at 110 ° C., whereby the epoxy groups derived from glycidyl methacrylate reacted with acrylic acid to cleave the epoxy groups, and at the same time, a polymerizable unsaturated bond was introduced into the side chain of the polymer. Next, 53.5 g of succinic anhydride was added to the reaction system, and the reaction was continued for 1 hour at 110 ° C., whereby the hydroxyl groups generated by the cleavage of the epoxy groups reacted with succinic anhydride to introduce carboxyl groups into the side chains, and a polymer (resin (C1)) was obtained.

[0429] Finally, 436.0 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (C1) solution with a polymer solid content of 40%.

[0430] The weight average molecular weight Mw of the produced resin (C1) was 6.7 × 10 ３The acid value calculated as solid content was 70 mg-KOH / g, and the double bond equivalent was 336 g / eq.

[0431] Synthesis Example 2: Synthesis of Resin (C2) 276.8 g of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, and the mixture was stirred while purging with nitrogen and heated to 120°C. Next, a monomer mixture consisting of 92.4 g of 2-ethylhexyl acrylate, 184.9 g of glycidyl methacrylate, and 12.3 g of dicyclopentanyl methacrylate, to which 35.3 g of t-butylperoxy-2-ethylhexanoate (polymerization initiator) had been added, was added dropwise from the dropping funnel to the flask over 2 hours. After completion of the dropwise addition, the mixture was stirred at 120°C for an additional 30 minutes to carry out a copolymerization reaction, thereby producing an addition copolymer.

[0432] Thereafter, the atmosphere in the flask was replaced with air, and 93.7 g of acrylic acid, 1.5 g of triphenylphosphine (catalyst), and 0.8 g of methoquinone (polymerization inhibitor) were added to the addition copolymer solution, and the reaction was continued for 10 hours at 110°C, whereby the epoxy groups derived from glycidyl methacrylate reacted with the acrylic acid to cleave the epoxy groups, and at the same time, a polymerizable unsaturated bond was introduced into the side chain of the polymer. Next, 24.2 g of succinic anhydride was added to the reaction system, and the reaction was continued for 1 hour at 110°C, whereby the hydroxyl groups generated by the cleavage of the epoxy groups reacted with the succinic anhydride to introduce carboxyl groups into the side chains, and a polymer (resin (C2)) was obtained.

[0433] Finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a resin (C2) solution with a polymer solid content of 40%.

[0434] The weight average molecular weight Mw of the resulting copolymer was 6.2 × 10 ３ The acid value calculated as solid content was 35 mg-KOH / g, and the double bond equivalent was 313 g / eq.

[0435] Synthesis Example 3: Synthesis of Resin (C3) A polymer (Resin (C3)) was obtained by adjusting the amounts of raw material monomers in the same manner as in the case of Resin (C1), and finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a Resin (C3) solution with a polymer solids content of 40%.

[0436] The weight average molecular weight Mw of the resulting copolymer was 4.96 × 10 ３ The acid value calculated as solid content was 37 mg-KOH / g, and the double bond equivalent was 344 g / eq.

[0437] Synthesis Example 4: Synthesis of Resin (C4) A polymer (Resin (C4)) was obtained by adjusting the amounts of raw material monomers in the same manner as in the case of Resin (C1), and finally, 383.3 g of propylene glycol monomethyl ether acetate was added to the reaction solution to obtain a Resin (C4) solution with a polymer solids content of 40%.

[0438] The weight average molecular weight Mw of the resulting copolymer was 4.91 × 10 ３ The acid value calculated as solid content was 42 mg-KOH / g, and the double bond equivalent was 514 g / eq.

[0439] Preparation Example 1 Preparation of Dispersion b of Semiconductor Particles (A) A toluene dispersion a of semiconductor particles (A) [green-emitting InP / ZnSeS quantum dots] containing oleic acid as the organic ligand (G) was prepared. After removing toluene from the toluene dispersion a by vacuum distillation, 70 parts of cyclohexyl acetate was added to 30 parts of the total amount of solids (semiconductor particles (A) and organic ligand (G)), to obtain a dispersion b of semiconductor particles (A).

[0440] The composition ratio of the semiconductor particles (A) to the organic ligands (G) was determined by measuring the amount of the semiconductor particles (A) remaining when the mixture after removing the toluene was heated to 550°C at a temperature increase rate of 5°C / min by TG-DTA measurement, and calculating the weight of the semiconductor particles (A) as the weight of the semiconductor particles (A).

[0441] (Preparation Example 2: Preparation of dispersion c of light scattering agent (B)) To 70 parts of titanium oxide nanoparticles, 3 parts in terms of solid content of BYK-LPN21116 (manufactured by BYK Japan) and propylene glycol monomethyl ether acetate (hereinafter referred to as "PGMEA") were added so that the total amount was 100 parts, and then the mixture was stirred with a paint shaker until sufficiently dispersed, thereby obtaining dispersion c of light scattering agent (B1) (solid content 73%).

[0442] (Example 1: Preparation of curable composition 1) Dispersion b of semiconductor particles (A), dispersion c of light scattering agent (B), and other components were mixed to prepare curable composition 1 having the composition shown in Table 1. In Table 1, the number of parts of components other than solvent (J) indicates the solid content equivalent value.

[0443]

[0444] Polymerizable compound (D1): carboxy group-containing polyfunctional (meth)acrylate (trade name "Aronix (registered trademark) M-510" manufactured by Toagosei Co., Ltd.) Polymerizable compound (D2): ethylene oxide-modified bisphenol A diacrylate, average molecular weight Mw: 512 Polymerization initiator (E1): compound represented by the following formula (EA-1)

[0445]

[0446] Antioxidant (Fb1): Trade name "Sumilizer (registered trademark) GP" manufactured by Sumitomo Chemical Co., Ltd. Leveling agent (H1): Polyether-modified silicone oil (Tora Silicone SH8400 trade name manufactured by Toray Dow Corning Co., Ltd.) Dispersant (I1): BYK-LPN21116 (manufactured by BYK Japan) Solvent (J1): Mixture of PGMEA (propylene glycol monomethyl ether acetate) and cyclohexyl acetate

[0447] Example 2 Preparation of Curable Composition 2 Curable composition 2 was prepared in the same manner as curable composition 1, except that resin (C2) was used instead of resin (C1).

[0448] (Example 3: Preparation of curable composition 3) Curable composition 3 was prepared in the same manner as curable composition 1, except that as the polymerizable compound (D), only the polymerizable compound (D2) was used without using the polymerizable compound (D1), and the amount of (D2) was 6.3 parts.

[0449] (Example 4: Preparation of curable composition 4) Curable composition 4 was prepared in the same manner as curable composition 1, except that as the polymerizable compound (D), only the polymerizable compound (D1) was used without using the polymerizable compound (D2), and the amount of (D1) was 6.3 parts.

[0450] Example 5 Preparation of Curable Composition 5 Curable composition 5 was prepared in the same manner as for curable composition 1, except that resin (C3) was used instead of resin (C1).

[0451] Example 6 Preparation of Curable Composition 6 Curable composition 6 was prepared in the same manner as for curable composition 1, except that resin (C4) was used instead of resin (C1).

[0452] (Example 7: Preparation of curable composition 7) Curable composition 7 was prepared in the same manner as curable composition 1, except that polymerizable compound (D3), which is dipentaerythritol polyacrylate (5 to 6 functional groups), was used instead of polymerizable compound (D2).

[0453] (Example 8: Preparation of curable composition 8) Curable composition 8 was prepared in the same manner as in the preparation of curable composition 1, except that the polymerization initiator (E1) was replaced with a polymerization initiator (E2) represented by the following formula (EB-1).

[0454]

[0455] (Example 9: Preparation of curable composition 9) Curable composition 9 was prepared in the same manner as curable composition 1, except that the polymerizable compound (D2) was replaced with a polymerizable compound (D3) that was a dipentaerythritol polyacrylate (5 to 6 functional groups), and the polymerization initiator (E2) represented by the above formula (EB-1) was used instead of the polymerization initiator (E1).

[0456] Comparative Example 1: Preparation of Curable Composition 10 Instead of the resin (C1), a resin having a structure different from that of the resin (C1) and a weight average molecular weight Mw of 6.2 × 10 ３ Curable composition 10 was prepared in the same manner as curable composition 1, except that resin (C5) having an acid value of 99 mg-KOH / g converted to solid content and a double bond equivalent of 0 was used.

[0457] Comparative Example 2 Preparation of Curable Composition 11 Curable composition 11 was prepared in the same manner as curable composition 1, except that resin (C5) was used instead of resin (C1), polymerizable compound (D3), which is dipentaerythritol polyacrylate (5 to 6 functional), was used instead of polymerizable compound (D2), and polymerization initiator (E2) represented by formula (EB-1) was used instead of polymerization initiator (E1).

[0458] Using the curable compositions 1 to 11, the development residual film rate and patterning property were evaluated in the following manner.

[0459] [Measurement of remaining film ratio] (i) On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated), any one of curable compositions 1 to 11 was applied by spin coating so that the film thickness after pre-baking was 5 μm, and then a drying step (pre-baking) was carried out at 70°C for 1 minute to form a film of the curable composition. Thereafter, without exposure, the substrate was developed using a developer (0.12% aqueous tetramethylammonium hydroxide solution) in a developing device (ADE-3000S, manufactured by Actes Kyosan Co., Ltd.), and the time until the coating film was completely removed was measured. (ii) After applying and pre-baking the curable composition in the same procedure as in (i) above, the substrate was exposed to 200 mJ / cm in air using an exposure machine (UPE-1255MA; manufactured by Ushio Lighting Co., Ltd.). ２ The exposure step was carried out by irradiating the film with light at an exposure dose of 1000 kJ / cm (based on a wavelength of 365 nm). Development was then carried out under the same conditions and for the same time as in (i) above, followed by rinsing with distilled water and then a thermal curing treatment (post-baking) at 95°C for 30 minutes, and the film thickness t1 was measured. (iii) A post-baked film (exposed film) was prepared in the same manner as in (ii) above, except that the development step was not carried out, and the film thickness t0 was measured. (iv) The ratio of the film thickness t1 to t0 (t1 / t0) was taken as the remaining film ratio.

[0460] [Evaluation of Patterning Ability] A pattern for evaluating patterning ability was prepared by the following method. Any one of curable compositions 1 to 11 was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the film thickness after pre-baking would be 5 μm, and then a drying step (pre-baking) was carried out at 70°C for 1 minute to form a film of the curable composition. After cooling the curable composition film after pre-baking, the film was exposed to light at 200 mJ / cm under atmospheric pressure using an exposure machine (UPE-1255MA; manufactured by Ushio Lighting Co., Ltd.) with a distance of 150 μm between the substrate on which the film was formed and a quartz glass photomask. ２ The film was irradiated with light at an exposure dose of 1000 kJ / cm (based on a wavelength of 365 nm). A photomask for forming a line-and-space pattern with a line width of 3 to 30 μm and a pattern spacing of 30 μm was used. The irradiated film was developed using a developer (an aqueous solution containing 0.12% tetramethylammonium hydroxide) in a developing device (ADE-3000S, manufactured by Actes Kyosan Co., Ltd.). The development time was the time required for the film to be completely removed when a separately prepared, unexposed film was developed under the same conditions. After rinsing with water, the film was post-baked in an oven at 95°C for 30 minutes to obtain a pattern consisting of a cured film having a line-and-space pattern (having 10 lines and 10 spaces for each line width of 3 μm, 5 μm, 10 μm, 20 μm, or 30 μm). The obtained pattern was observed using a microscope (magnification 200x; VHX-2000; manufactured by Keyence Corporation), and the smallest line width at which the exposed pattern remained partially or completely was used as an index of the patterning ability of the composition.

[0461] [Measurement of Fluorescence Emission Intensity of Cured Film] Any of the curable compositions 1 to 11 was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the film thickness after post-baking would be 5 μm, and then a drying step (pre-baking) was carried out at 70° C. for 1 minute to form a film of the curable composition 1 to 11. After cooling, the film was exposed to 200 mJ / cm 2 in air using an exposure machine (UPE-1255MA; manufactured by Ushio Lighting Co., Ltd.). ２An exposure step was carried out by irradiating the substrate with light at an exposure dose of 1000 W (based on a wavelength of 365 nm), followed by a thermal curing step (post-baking) at 95°C for 30 minutes to obtain a substrate having a cured film. Next, a surface-emitting backlight (OPSM series: manufactured by Optex FA) equipped with an LED lamp having an emission peak wavelength of 450 nm and a diffuser plate was prepared as a backlight. The backlight was installed with the diffuser plate facing upward, and a spectroradiometer (SR-UL1R: manufactured by Topcon Technohouse) was installed at a height of 60 cm from the surface of the diffuser plate. A glass substrate (Eagle 2000: manufactured by Corning) was installed as a reference on the surface of the diffuser plate of the backlight. The backlight was turned on in this state, and the integrated value of the spectral irradiance of the backlight in the wavelength range of 380 nm to 480 nm was measured through the glass substrate as a reference, at 2.69 W·sr. －１ ・m －２ The light intensity of the backlight was adjusted so that the value was 0.01. Next, the glass substrate used as a reference was removed, and a 5 cm square substrate having a cured film obtained from any of the above-mentioned curable compositions 1 to 11 was placed on the surface of the diffusion plate of the backlight. In this state, the backlight was turned on, and the luminous intensity (unit: mW sr) of the light emitted from the cured film was measured as the integrated spectral irradiance in the wavelength range of 480 nm to 780 nm. ―１ ・m ―２ ) was measured.

[0462] The results of the measurement of the remaining film rate, the evaluation of the patterning property, and the measurement of the fluorescence emission intensity of the cured film are shown in Table 2.

[0463]

[0464] For Examples 1 and 2 and Comparative Example 1, the film remaining rate was measured in the same manner except that the pre-baking conditions were 100° C. for 3 minutes and the post-baking conditions were 180° C. for 30 minutes. The results are shown in Table 3.

[0465]

[0466] According to Table 2, in Examples 1 to 9 which satisfied the requirements of the present invention, the film remaining ratio was good when the curable composition was cured at low temperature, whereas in Comparative Examples 1 and 2, the film remaining ratio was lower when the cured composition was cured at low temperature compared to Examples 1 to 9. From Table 3, it can be seen that Comparative Example 1 also had a good film remaining ratio when cured at high temperature, and that the problem of a decrease in film remaining ratio did not occur when conventional curable compositions were cured at high temperatures.

Claims

1. A curable composition containing semiconductor particles (A) and a resin (C), wherein the value X calculated by the following formula (1) from the acid value and the weight average molecular weight Mw of the resin (C) is 10 or more and 59.75 or less, and the double bond equivalent of the resin (C) is 100 g / eq or more and less than 600 g / eq. X = {acid value (mg-KOH / g) × weight average molecular weight Mw} / 10,000…(1) 2. The curable composition according to claim 1, wherein the acid value of the resin (C) is less than 85 mg-KOH / g.

3. The curable composition according to claim 1, wherein the weight average molecular weight Mw of the resin (C) is 5000 or more.

4. The curable composition according to claim 1, wherein the mass ratio (A / C) of the semiconductor particles (A) to the resin (C) is 0.65 or more.

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

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

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

8. The curable composition according to claim 1, further containing a light scattering agent (B).

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