WO2024084904A1 - Composition durcissable, film durci et dispositif d'affichage - Google Patents

Composition durcissable, film durci et dispositif d'affichage Download PDF

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WO2024084904A1
WO2024084904A1 PCT/JP2023/034842 JP2023034842W WO2024084904A1 WO 2024084904 A1 WO2024084904 A1 WO 2024084904A1 JP 2023034842 W JP2023034842 W JP 2023034842W WO 2024084904 A1 WO2024084904 A1 WO 2024084904A1
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curable composition
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寛 岩脇
真芳 ▲徳▼田
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/10—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to inorganic materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/854—Arrangements for extracting light from the devices comprising scattering means
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • the present invention relates to a curable composition, a cured film formed therefrom, and a display device including the cured film.
  • Patent Document 1 describes a curable composition that can form a cured film by an inkjet method as a curable composition for forming a cured film such as a wavelength conversion film included in a display device.
  • the present invention provides a curable composition, a cured film, and a display device as described below.
  • a curable composition comprising semiconductor particles (A), a polymerizable compound (B), a polymerization initiator (C) and an antioxidant (D),
  • the curable composition contains, as the polymerizable compound (B), 40 mass % or more of a polymerizable compound having a dipole moment of 3D or more, based on the total amount of the polymerizable compound (B).
  • the polymerizable compound (B) contains a bifunctional polymerizable compound having a dipole moment of 3D or more in an amount of 40 mass% or more relative to the total amount of the polymerizable compound (B).
  • a curable composition comprising semiconductor particles (A), a polymerizable compound (B), a polymerization initiator (C) and an antioxidant (D),
  • the curable composition contains a polymerizable compound (B) having a dipole moment of 3D or more in an amount of 20 mass% or more relative to the total amount of the curable composition.
  • the polymerizable compound (B) contains a bifunctional polymerizable compound having a dipole moment of 3D or more in an amount of 20 mass% or more relative to the total amount of the curable composition.
  • curable composition that contains luminescent semiconductor particles and that can suppress weight loss during storage. It is also possible to provide a cured film formed from the curable composition, and a display device that includes the cured film.
  • FIG. 2 is a schematic cross-sectional view showing an example of a display member.
  • the curable composition according to the present invention (hereinafter, also simply referred to as "curable composition”) contains semiconductor particles (A), a polymerizable compound (B), a polymerization initiator (C), and an antioxidant (D).
  • curable composition contains semiconductor particles (A), a polymerizable compound (B), a polymerization initiator (C), and an antioxidant (D).
  • components that are contained or can be contained in the curable composition will be described.
  • the compounds exemplified as each component that is or can be contained in the curable composition may be used alone or in combination of two or more types, unless otherwise specified.
  • the semiconductor particles (A) emit light of a wavelength different from the primary light, and preferably convert the wavelength of blue light, which is the primary light, into a wavelength of light of a different color.
  • the semiconductor particles (A) preferably emit green or red light, and more preferably absorb blue light and emit green or red light.
  • blue refers to all light that is perceived as blue (all light having intensity in the blue wavelength range, e.g., 380 nm to 495 nm), and is not limited to light of a single wavelength.
  • Green refers to all light that is perceived as green (all light having intensity in the green wavelength range, e.g., 495 nm to 585 nm), and is not limited to light of a single wavelength.
  • Red refers to all light that is perceived as red (all light having intensity in the red wavelength range, e.g., 585 nm to 780 nm), and is not limited to light of a single wavelength.
  • yellow refers to all light that is perceived as yellow (all light having intensity in the yellow wavelength range, e.g., 560 nm to 610 nm), and is not limited to light of a single wavelength.
  • the emission spectrum of the green-emitting semiconductor particles (A) preferably includes a peak having a maximum value in the wavelength range of 500 nm to 560 nm, more preferably includes a peak having a maximum value in the wavelength range of 520 nm to 545 nm, and even more preferably includes a peak having a maximum value in the wavelength range of 525 nm to 535 nm. This allows the displayable color gamut of green light of the display device to be expanded.
  • the peak preferably has a full width at half maximum of 15 nm to 80 nm, more preferably 15 nm to 60 nm, even more preferably 15 nm to 50 nm, and particularly preferably 15 nm to 45 nm. This allows the displayable color gamut of green light of the display device to be expanded.
  • the emission spectrum of the semiconductor particles (A) emitting red light preferably includes a peak having a maximum value in a wavelength range of 610 nm to 750 nm, more preferably includes a peak having a maximum value in a wavelength range of 620 nm to 650 nm, and even more preferably includes a peak having a maximum value in a wavelength range of 625 nm to 645 nm. This allows the displayable color gamut of red light of the display device to be expanded.
  • the peak preferably has a full width at half maximum of 15 nm to 80 nm, more preferably 15 nm to 60 nm, even more preferably 15 nm to 50 nm, and particularly preferably 15 nm to 45 nm. This allows the displayable color gamut of red light of the display device to be expanded.
  • the emission spectrum of the semiconductor particles (A) is measured according to the method described in the Examples section below.
  • 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 semiconductor particles with a particle diameter of 1 nm to 100 nm, which utilize the band gap of the semiconductor to absorb ultraviolet light or visible light (e.g., blue light) and emit light.
  • Quantum dots include, for example, 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, HgZ Compounds of Group 12 elements and Group 16 elements such as nSeTe and HgZn
  • quantum dots When the quantum dots contain S or Se, quantum dots whose surfaces are modified with a metal oxide or an organic substance may be used. By using surface-modified quantum dots, it is possible to prevent S or Se from being extracted by a reactive component that is or may be contained in composition I.
  • 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.
  • quantum dots 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.
  • the light emitted from quantum dots has a narrow spectral width, which is advantageous for widening the color gamut of display devices.
  • quantum dots have high responsiveness, which is also advantageous in terms of the efficiency of using primary light.
  • the perovskite compound is a compound having a perovskite type crystal structure, which is composed of A, B and X.
  • 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.
  • 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 kind of ion selected from the group consisting of halide ions and thiocyanate ions.
  • B is a component located at the center of a hexahedron having A as a vertex and an octahedron having X as a vertex in the perovskite crystal structure, and is a metal ion.
  • 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.
  • the perovskite compound is represented as ABX (3+ ⁇ ) .
  • the perovskite compound is represented by A 2 BX (4+ ⁇ ) .
  • ⁇ is a number that can be appropriately changed depending on the charge balance of B, and is equal to or greater than ⁇ 0.7 and equal to or less than 0.7.
  • perovskite compound having a two-dimensional perovskite-type crystal structure represented by A 2 BX (4+ ⁇ ) include: ( C4H9NH3 ) 2PbBr4 , ( C4H9NH3 ) 2PbCl4 , ( C4H9NH3) 2PbI4 , ( C7H15NH3 ) 2PbBr4 , ( C7H15NH3 ) 2PbCl4 , ( C7H15NH3 ) 2PbI4 , (C4H9NH3 ) 2Pb (1-a ) LiaBr (4+ ⁇ ) (0 ⁇ a ⁇ 0.7, -0.7 ⁇ ⁇ 0 ) , ( C4H9NH3 ) 2Pb ( 1 -a ) NaaBr (4+ ⁇ ) (0 ⁇ a ⁇ 0.7, -0.7 ⁇ ⁇ 0), ( C4H9NH3 ) 2Pb (1-a) Rb aBr (4+ ⁇ ) (0 ⁇
  • the curable composition may contain two or more types of semiconductor particles (A).
  • the curable composition may contain only one type of semiconductor particles (A) that absorb primary light and emit green light, or may contain two or more types in combination.
  • the curable composition may contain only one type of semiconductor particles (A) that absorb primary light and emit red light, or may contain two or more types in combination.
  • the semiconductor particles (A) may be ligand-containing semiconductor particles that contain an organic ligand (G) that coordinates to the semiconductor particles.
  • 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 organic ligand (G) is an organic compound having a polar group
  • the organic ligand (G) usually coordinates to the semiconductor particles via the polar group.
  • the semiconductor particles (A) may contain one or more organic ligands (G).
  • the inclusion of the organic ligand (G) in the semiconductor particles (A) can be advantageous from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film. Coordination of the organic ligand (G) to the semiconductor particles is confirmed by the fact that the semiconductor particles are uniformly dispersed in a dispersion medium suitable for the organic ligand.
  • the polar group of the organic ligand (G) is, for example, at least one group selected from the group consisting of a thiol group (-SH), a carboxy group (-COOH), and an amino group (-NH 2 ).
  • a polar group selected from this group can be advantageous in terms of increasing the coordination ability to the semiconductor particles. High coordination ability can contribute to improving the stability and dispersibility of the semiconductor particles (A) in the curable composition, as well as improving the luminescence intensity of the curable composition and the cured film. Among them, 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.
  • the organic ligand (G) is, for example, a compound represented by the following formula (x): XA- RX ( x)
  • X 1 A is the polar group described above
  • R 1 X is a monovalent hydrocarbon group which may contain a heteroatom (N, O, S, a 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, and may be 1 to 30.
  • the 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.
  • the group R 1 X may contain a polar group, specific examples of which are given in the above description of the polar group X 1 A.
  • organic ligands having a carboxy group as the polar group XA include formic acid, acetic acid, and propionic acid, as well as saturated or unsaturated fatty acids.
  • 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, ⁇ -linolenic acid, ⁇ -linolenic acid, stearic acid, dihomo- ⁇ -linolenic acid,
  • organic ligand having a thiol group or an amino group as the polar group XA include organic ligands in which the carboxy group of the organic ligand having a carboxy group as the polar group XA exemplified above is replaced with a thiol group or an amino group.
  • organic ligands represented by the above formula (x) include compound (G-1) and compound (G-2).
  • 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)
  • 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 become a ligand that coordinates to the semiconductor particles.
  • the semiconductor particles (A) may contain only one type of compound (G-1), or may contain two or more types of compound (G-1).
  • compound (G-1) is a compound represented by the following formula (G-1a).
  • Compound (G-1) may be an acid anhydride of the compound represented by formula (G-1a).
  • R 3 B represents a divalent hydrocarbon group. When a plurality of R 3 B are present, they may be the same or different.
  • the hydrocarbon group may have one or more substituents. When a plurality of substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which they are bonded.
  • -CH 2 - contained in the hydrocarbon group may be replaced by at least one of -O-, -S-, -SO 2 -, -CO- and -NH-.
  • p represents an integer of 1 to 10.
  • Examples of the divalent hydrocarbon group represented by R 3 B include a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.
  • chain hydrocarbon groups examples include linear or branched alkanediyl groups, which usually have 1 to 50 carbon atoms, preferably 1 to 20, and more preferably 1 to 10.
  • alicyclic hydrocarbon groups examples include monocyclic or polycyclic cycloalkanediyl groups, which usually have 3 to 50 carbon atoms, preferably 3 to 20, and more preferably 3 to 10.
  • aromatic hydrocarbon groups include monocyclic or polycyclic arenediyl groups, which usually have 6 to 20 carbon atoms.
  • Examples of the substituents that the above-mentioned 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 substituents that the above-mentioned hydrocarbon group may have are preferably a carboxy group, an amino group, or a halogen atom.
  • —CH 2 — contained in the above hydrocarbon group is replaced by at least one of —O—, —CO— and —NH—
  • —CH 2 — is replaced by at least one of —CO— and —NH—, more preferably by —NH—.
  • Examples of the compound represented by formula (G-1a) include compounds represented by the following formulas (1-1) to (1-9).
  • Specific examples of compounds 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.
  • compound (G-1) is a polyvalent carboxylic acid compound, preferably a compound (G-1b) represented by the above formula (G-1a) in which -SH in formula (G-1a) is replaced with a carboxy group (-COOH).
  • Examples of the compound (G-1b) include the following compounds. 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-cyclohexene
  • the molecular weight of the compound (G-1) is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, still more preferably 1000 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.
  • the above molecular weight may be a number average molecular weight or a weight average molecular weight.
  • the number average molecular weight and the weight average molecular weight are the number average molecular weight and the weight average molecular weight, respectively, calculated in terms of standard polystyrene as measured by gel permeation chromatography (GPC).
  • the content ratio of compound (G-1) to the semiconductor particles is, in mass ratio, preferably 0.001 to 1, more preferably 0.01 to 0.5, and even more preferably 0.02 to 0.45. Having the content ratio within this range can be advantageous from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film.
  • the content of compound (G-1) in the curable composition is, from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film, preferably 0.1% by mass or more and 20% by mass or less, more preferably 0.2% by mass or more and 20% by mass or less, even more preferably 0.2% by mass or more and 10% by mass or less, still more preferably 0.5% by mass or more and 10% by mass or less, and particularly preferably 0.5% by mass or more and 8% by mass or less, based on the total amount of solids in the curable composition.
  • 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 (wherein the carbon atom in the carbon chain may be replaced with another atom such as an oxygen atom) in compound (G-2).
  • the semiconductor particles (A) may contain only one type of compound (G-2), or may contain two or more types of compound (G-2).
  • the semiconductor particles (A) may contain the compound (G-1) or the compound (G-2), or may contain the compound (G-1) and the compound (G-2).
  • the 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 polyalkylene glycol structure is the following formula:
  • R 3 C is an alkylene group, for example, an ethylene group, a propylene group, etc.
  • G-2a A specific example of compound (G-2) is a polyalkylene glycol compound represented by the following formula (G-2a):
  • X is a polar group
  • Y is a monovalent group
  • Z 1 C is a divalent or trivalent group
  • n is an integer of 2 or more
  • m is 1 or 2
  • R 1 C is an alkylene group.
  • the polar group X is preferably at least one group selected from the group consisting of a thiol group (-SH), a carboxy group (-COOH), and an amino group (-NH 2 ).
  • a polar group selected from this group can be advantageous in terms of enhancing coordination to the semiconductor particles.
  • the polar group X is at least one group selected from the group consisting of a thiol group and a carboxy group.
  • 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, a halogen atom, 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.
  • Examples of the group Y include an alkyl group having a linear, branched or cyclic structure and a carbon number of 1 to 12; and an alkoxy group having a linear, branched or cyclic structure and a carbon number of 1 to 12.
  • the number of carbon atoms in the alkyl group and alkoxy group is preferably 1 to 8, more preferably 1 to 6, and even more preferably 1 to 4.
  • the -CH 2 - contained in the alkyl group and alkoxy group may be substituted with -O-, -S-, -C( ⁇ O)-, -C( ⁇ O)-O-, -O-C( ⁇ O)-, -C( ⁇ O)-NH-, -NH-, or the like.
  • the group Y is preferably a linear or branched alkoxy group having a carbon number of 1 to 4, and more preferably a linear alkoxy group having a carbon number of 1 to 4.
  • the group Y may contain a polar group.
  • the polar group may be at least one group selected from the group consisting of a thiol group (-SH), a carboxy group (-COOH), and an amino group (-NH 2 ).
  • 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.
  • the group Z 1 C is a divalent or trivalent group.
  • the group Z 1 C is not particularly limited, and may be a divalent or trivalent hydrocarbon group which may contain a heteroatom (N, O, S, halogen atom, etc.).
  • the number of carbon atoms in the hydrocarbon group is, for example, 1 to 24.
  • the hydrocarbon group may have an unsaturated bond.
  • Examples of the divalent group Z 3 C include an alkylene group having 1 to 24 carbon atoms and a linear, branched or cyclic structure; an alkenylene group having 1 to 24 carbon atoms and a linear, branched or cyclic structure.
  • the number of carbon atoms in the alkyl group and the alkenylene group is preferably 1 to 12, more preferably 1 to 8, and even more preferably 1 to 4.
  • the -CH 2 - contained in the alkyl group and the alkenylene group may be substituted with -O-, -S-, -C( ⁇ O)-, -C( ⁇ O)-O-, -O-C( ⁇ O)-, -C( ⁇ O)-NH-, -NH-, or the like.
  • Examples of the trivalent group Z 3 C include a group obtained by removing one hydrogen atom from the divalent group Z 3 C.
  • the group Z 1 C may have a branched structure.
  • the group Z 1 C having a branched structure may have a polyalkylene glycol structure other than the polyalkylene glycol structure shown in the above formula (G-2a) in a branched chain other than the branched chain containing the polyalkylene glycol structure shown in the above formula (G-2a).
  • the group Z 1 C 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.
  • R 3 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.
  • 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.
  • the molecular weight of compound (G-2) may be, for example, about 150 or more and 10,000 or less, but from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film, it 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 the number average molecular weight and the weight average molecular weight, respectively, in terms of standard polystyrene measured by GPC.
  • the content ratio of compound (G-2) to the semiconductor particles is, in mass ratio, preferably 0.001 to 2, more preferably 0.01 to 1.5, and even more preferably 0.1 to 1.
  • a content ratio within this range can be advantageous from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film.
  • the content of compound (G-2) in the curable composition is preferably 0.1% by mass or more and 40% by mass or less, more preferably 0.1% by mass or more and 20% by mass or less, even more preferably 1% by mass or more and 15% by mass or less, and even more preferably 2% by mass or more and 12% by mass or less, based on the total amount of solids in the curable composition, from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film.
  • the ratio of the content of the organic ligand (G) to the semiconductor particles 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. Having the content ratio within this range can be advantageous from the viewpoint of improving the stability and dispersibility of the semiconductor particles (A) and the luminescence intensity of the curable composition and the cured film.
  • the content of the organic ligand (G) here refers to the total content of all organic ligands contained in the curable composition.
  • the content M A of the semiconductor particles (A) is preferably 10% by mass or more, more preferably 16% by mass or more, even more preferably 17% by mass or more, even more preferably 18% by mass or more, particularly preferably 20% by mass or more, most preferably 25% by mass or more, and is preferably 45% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less, based on the total amount of the curable composition. If the content M A of the semiconductor particles (A) is within the above range, it can be advantageous from the viewpoint of improving the luminescence intensity of the curable composition and the cured film.
  • the content M A of the semiconductor particles (A) is the content of the ligand-containing semiconductor particles when the semiconductor particles (A) are ligand-containing semiconductor particles containing an organic ligand (G).
  • the content of the semiconductor particles (A) relative to the total amount of solids in the curable composition is preferably within the same range as above.
  • the total amount of solids in the curable composition means the total of the components contained in the curable composition excluding the solvent (F).
  • the content in the solids of the curable composition can be measured by a 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 at the time of preparing the curable composition.
  • the curable composition may contain two or more types of semiconductor particles (A).
  • the above content of semiconductor particles (A) means the total content of two or more types of semiconductor particles (A).
  • the curable composition contains a polymerizable compound (B).
  • the polymerizable compound (B) is a compound that can be polymerized by an active radical, an acid, or the like generated from a polymerization initiator (C) described later.
  • the curable composition may contain two or more types of polymerizable compounds (B).
  • the polymerizable compound (B) may be a photopolymerizable compound that is cured by irradiation with light, or a thermally polymerizable compound that is cured by heat.
  • the photopolymerizable compound may be a photoradical polymerizable compound that is cured by a radical polymerization reaction by irradiation with light, or a photocationic polymerizable compound that is cured by a cationic polymerization reaction by irradiation with light.
  • the photopolymerizable compound is preferably a photoradical polymerizable compound.
  • the weight average molecular weight of the photopolymerizable compound is, for example, 150 or more and 3000 or less, preferably 150 or more and 2900 or less, and more preferably 250 or more and 1500 or less.
  • Examples of the photoradical polymerizable compound include compounds having a polymerizable ethylenically unsaturated bond, and among these, (meth)acrylate compounds are preferred.
  • Examples of the (meth)acrylate compound include a monofunctional (meth)acrylate compound having one (meth)acryloyloxy group in the molecule (hereinafter also referred to as "compound (B-1)”); a bifunctional (meth)acrylate compound having two (meth)acryloyloxy groups in the molecule (hereinafter also referred to as “compound (B-2)”); and a polyfunctional (meth)acrylate compound having three or more (meth)acryloyloxy groups in the molecule (hereinafter also referred to as “compound (B-3)”).
  • compound (B-1) a monofunctional (meth)acrylate compound having one (meth)acryloyloxy group in the molecule
  • compound (B-2) a bifunctional (meth)acrylate compound having two (meth
  • Examples of compound (B-1) include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, dodecyl (meth)acrylate (lauryl (meth)acrylate), hexadecyl (meth)acrylate, octadecyl (meth)acrylate, cyclohexyl (meth)acrylate, methoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxyethyl (meth)acrylate, glycidyl (meth)acrylate, dimethylaminoeth
  • the compound (B-2) may be diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,8- Octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth
  • Examples of the compound (B-3) include glycerin tri(meth)acrylate, 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 trimethylol
  • the number of (meth)acryloyloxy groups in one molecule of compound (B-3) is, for example, 3 or more and 6 or less, preferably 3 or more and 5 or less, and more preferably 3.
  • a photoradical polymerizable compound is a (meth)acrylate compound having a vinyl ether group and a (meth)acryloyl group (preferably a (meth)acryloyloxy group) in the same molecule (hereinafter also referred to as "compound (B-4)").
  • Compound (B-4) can be a compound belonging to any of compounds (B-1) to (B-3).
  • the number of vinyl ether groups in compound (B-4) is preferably 1 to 4, more preferably 1 to 2, and particularly preferably 1.
  • the number of (meth)acryloyl groups in compound (B-4) is preferably 1 to 4, more preferably 1 to 2, and particularly preferably 1.
  • Examples of the compound (B-4) include 2-vinyloxyethyl (meth)acrylate, 3-vinyloxypropyl (meth)acrylate, 2-vinyloxypropyl (meth)acrylate, 1-vinyloxypropyl (meth)acrylate, 1-methyl-2-vinyloxyethyl (meth)acrylate, 4-vinyloxybutyl (meth)acrylate, 3-vinyloxybutyl (meth)acrylate, 2-vinyloxybutyl (meth)acrylate, 1-methyl-3-vinyloxypropyl (meth)acrylate, and 2-methyl-3-vinyloxypropyl (meth)acrylate.
  • the compound (B-4) is preferably a vinyloxy C 1-6 alkyl (meth)acrylate or a (vinyloxy C 1-4 alkoxy) C 1-4 alkyl (meth)acrylate, more preferably a (vinyloxy C 1-4 alkoxy) C 1-4 alkyl (meth)acrylate, and particularly preferably 2-(2-vinyloxyethoxy)ethyl (meth)acrylate.
  • the polymerizable compound (B) is preferably a photoradical polymerizable compound which is an amine compound or an amide compound, and the content of the photoradical polymerizable compound is preferably less than 20 mass%, more preferably less than 10 mass%, even more preferably less than 5 mass%, relative to the total amount of the curable composition, and even more preferably is not contained. If the radical polymerizable compound is contained, the luminescence characteristics of the semiconductor particles (A) in the curable composition or the cured film may be deteriorated.
  • photocationically polymerizable compounds include compounds having at least one oxetane ring (four-membered ring ether) in the molecule (hereinafter simply referred to as “oxetane compounds”), compounds having at least one oxirane ring (three-membered ring ether) in the molecule (hereinafter simply referred to as “epoxy compounds”), and vinyl ether compounds.
  • oxetane compounds include 3-ethyl-3-hydroxymethyloxetane, 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 3-ethyl-3-(phenoxymethyl)oxetane, di[(3-ethyl-3-oxetanyl)methyl]ether, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, and phenol novolac oxetane.
  • oxetane compounds are readily available commercially, and examples of commercially available products include ARON OXETANE (registered trademark) OXT-101, ARON OXETANE (registered trademark) OXT-121, ARON OXETANE (registered trademark) OXT-211, ARON OXETANE (registered trademark) OXT-221, and ARON OXETANE (registered trademark) OXT-212, all of which are sold by Toagosei Co., Ltd.
  • Epoxy compounds include aromatic epoxy compounds, glycidyl ethers of polyols having an alicyclic ring, aliphatic epoxy compounds, alicyclic epoxy compounds, etc.
  • Aromatic epoxy compounds include bisphenol-type epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, and diglycidyl ether of bisphenol S; novolac-type epoxy resins such as phenol novolac epoxy resin, cresol novolac epoxy resin, and hydroxybenzaldehyde phenol novolac epoxy resin; and multifunctional epoxy resins such as glycidyl ether of tetrahydroxyphenylmethane, glycidyl ether of tetrahydroxybenzophenone, and epoxidized polyvinylphenol.
  • bisphenol-type epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, and diglycidyl ether of bisphenol S
  • novolac-type epoxy resins such as phenol novolac epoxy resin, cresol novolac epoxy resin, and hydroxybenzaldehyde phenol novolac epoxy resin
  • multifunctional epoxy resins such as
  • Glycidyl ethers of polyols having alicyclic rings include those obtained by selectively hydrogenating aromatic rings of aromatic polyols under pressure in the presence of a catalyst, and then glycidyl etherifying the resulting nuclear hydrogenated polyhydroxy compounds.
  • aromatic polyols include bisphenol-type compounds such as bisphenol A, bisphenol F, and bisphenol S; novolac-type resins such as phenol novolac resin, cresol novolac resin, and hydroxybenzaldehyde phenol novolac resin; and polyfunctional compounds such as tetrahydroxydiphenylmethane, tetrahydroxybenzophenone, and polyvinylphenol.
  • Glycidyl ethers can be obtained by reacting epichlorohydrin with alicyclic polyols obtained by hydrogenating aromatic rings of these aromatic polyols.
  • the preferred one is the diglycidyl ether of hydrogenated bisphenol A.
  • Aliphatic epoxy compounds include polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts. Specific examples include diglycidyl ether of 1,4-butanediol; diglycidyl ether of 1,6-hexanediol; triglycidyl ether of glycerin; triglycidyl ether of trimethylolpropane; diglycidyl ether of polyethylene glycol; diglycidyl ether of propylene glycol; diglycidyl ether of neopentyl glycol; and polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides (ethylene oxide or propylene oxide) to aliphatic polyhydric alcohols such as ethylene glycol, propylene glycol, or glycerin.
  • alkylene oxides ethylene oxide or propylene oxide
  • Alicyclic epoxy compounds are compounds that have at least one structure in the molecule that forms an oxirane ring together with the carbon atoms of the alicyclic ring, and examples that can be used include the "Celloxide” series and “Cyclomer” (all manufactured by Daicel Corporation), and the “Cyracure UVR” series (manufactured by The Dow Chemical Company).
  • Vinyl ether compounds include 2-hydroxyethyl vinyl ether, triethylene glycol vinyl monoether, tetraethylene glycol divinyl ether, trimethylolpropane trivinyl ether, etc.
  • the content M of the polymerizable compound (B) is preferably 20 mass% or more and 90 mass% or less, more preferably 30 mass% or more and 88 mass% or less, even more preferably 40 mass% or more and 86 mass% or less, still more preferably 45 mass% or more and 84 mass% or less, particularly preferably 50 mass% or more and 82 mass% or less, and may be 80 mass% or less, 75 mass% or less, or 70 mass% or less, based on the total amount of the curable composition.
  • the content of the polymerizable compound (B) relative to the total amount of solids in the curable composition is preferably 20 mass% or more and 90 mass% or less, more preferably 30 mass% or more and 88 mass% or less, even more preferably 40 mass% or more and 86 mass% or less, still more preferably 45 mass% or more and 84 mass% or less, particularly preferably 50 mass% or more and 82 mass% or less, and may be 80 mass% or less, 75 mass% or less, or 70 mass% or less.
  • the curable composition satisfies at least one of the following (i) or (ii).
  • the polymerizable compound (B) contains a polymerizable compound (hereinafter also referred to as "polymerizable compound (Bx)") having a dipole moment of 3D (Debye) or more in an amount of 40 mass% or more based on the total amount of the polymerizable compound (B).
  • the polymerizable compound (B) contains the polymerizable compound (Bx) in an amount of 20 mass% or more based on the total amount of the curable composition.
  • weight loss By satisfying at least one of the above (i) or (ii), it is possible to suppress the weight loss (hereinafter, simply referred to as "weight loss") of the curable composition due to storage. In addition, by satisfying at least one of the above (i) or (ii), it is possible to provide a curable composition that can suppress the weight loss due to storage, has good film-forming properties, and can form a cured film with suppressed wrinkles, and can form a cured film with good luminescence intensity.
  • the curable composition that can suppress the weight loss due to storage, has low viscosity, can form a cured film with suppressed wrinkles, and can form a cured film with good luminescence intensity. From the viewpoint of suppressing weight loss, further from the viewpoint of increasing film-forming properties and luminescence intensity, and from the viewpoint of reducing the viscosity of the curable composition, it is preferable that the curable composition satisfies both of the above (i) and (ii).
  • the polymerizable compound (B) may contain two or more kinds of polymerizable compounds (Bx).
  • the content of the polymerizable compound (Bx) in the above (i) and (ii) is the total content of two or more kinds of polymerizable compounds (Bx) relative to the total amount of the polymerizable compound (B) and the total amount of the curable composition, respectively.
  • the dipole moment of the polymerizable compound (Bx) is preferably 3.2D or more, more preferably 3.4D or more, and even more preferably 3.6D or more.
  • the dipole moment of the polymerizable compound (Bx) is usually 10D or less, and may be 8.0D or less, 7.0D or less, 6.5D or less, 6.0D or less, or 5.5D or less.
  • the weight loss rate of the curable composition is preferably 4.0% by mass or less, more preferably 3.0% by mass or less, even more preferably 2.0% by mass or less, even more preferably 1.0% by mass or less, particularly preferably 0.5% by mass or less, and most preferably 0.1% by mass or less (e.g., 0.0% by mass).
  • the dipole moment of a polymerizable compound can be determined based on its molecular structure by DFT (Density Functional Theory; B3LYP/6-31G+g(d)) calculation using general calculation software.
  • Examples of calculation software include the quantum chemistry calculation program "Gaussian series" manufactured by HULINKS.
  • the dipole moment of a polymerizable compound depends on the electronegativity, three-dimensional structure, etc. of the atoms constituting the polymerizable compound.
  • the content of the polymerizable compound (Bx) is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, still more preferably 80% by mass or more, particularly preferably 90% by mass or more, and even more particularly preferably 95% by mass or more (e.g., 100% by mass) based on the total amount of the polymerizable compound (B).
  • the content may be 100% by mass or less, 90% by mass or less, or 80% by mass or less.
  • the content of the polymerizable compound (Bx) is preferably 30% by mass or more, more preferably 40% by mass or more, even more preferably 50% by mass or more, still more preferably 60% by mass or more, and particularly preferably 65% by mass or more, based on the total amount of the curable composition.
  • the content may be 90% by mass or less or 85% by mass or less.
  • the polymerizable compound (B) contains a bifunctional polymerizable compound having a dipole moment of 3D or more (hereinafter also referred to as "polymerizable compound (Bx-2)").
  • a bifunctional polymerizable compound is a compound having two polymerizable groups in the molecule.
  • An example of a bifunctional polymerizable compound is the bifunctional (meth)acrylate compound described above.
  • the polymerizable compound (Bx-2) is preferably a bifunctional (meth)acrylate compound having a dipole moment of 3D or more.
  • the dipole moment of the polymerizable compound (Bx-2) is preferably 3.2D or more, more preferably 3.4D or more, even more preferably 3.6D or more, even more preferably 3.8D or more, particularly preferably 4.0D or more, and most preferably 4.2D or more.
  • the dipole moment of the polymerizable compound (Bx-2) is usually 8.0D or less, and may be 7.0D or less, 6.5D or less, 6.0D or less, or 5.0D or less.
  • the content of the polymerizable compound (Bx-2) is preferably 40% by mass or more, more preferably 50% by mass or more, even more preferably 60% by mass or more, still more preferably 70% by mass or more, particularly preferably 80% by mass or more, particularly preferably 90% by mass or more, and even more particularly preferably 95% by mass or more (for example, 100% by mass) based on the total amount of the polymerizable compound (B).
  • the content may be 100% by mass or less, 95% by mass or less, 90% by mass or less, 80% by mass or less, or 70% by mass or less.
  • the content of the polymerizable compound (Bx-2) is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, still more preferably 50% by mass or more, and particularly preferably 60% by mass or more, based on the total amount of the curable composition.
  • the content may be 90% by mass or less, 85% by mass or less, or 80% by mass or less.
  • the polymerizable compound (B) may contain two or more kinds of polymerizable compounds (Bx-2).
  • the above content of the polymerizable compound (Bx-2) is the total content of two or more kinds of polymerizable compounds (Bx-2) relative to the total amount of the polymerizable compound (B) and the total amount of the curable composition, respectively.
  • the polymerizable compound (B) may contain a polyfunctional polymerizable compound in addition to the polymerizable compound (Bx-2).
  • the polyfunctional polymerizable compound referred to here means a compound having three or more polymerizable groups in the molecule.
  • Examples of the polyfunctional polymerizable compound include the above-mentioned polyfunctional (meth)acrylate compounds.
  • the (meth) groups contained in one molecule of the polyfunctional (meth)acrylate compound may be exemplified by the following polyfunctional (meth)acrylate compounds:
  • the number of acryloyloxy groups is, for example, 3 or more and 6 or less, preferably 3 or more and 5 or less, and more preferably 3.
  • the use of a polyfunctional polymerizable compound in combination with the polymerizable compound (Bx-2) may further suppress weight loss.
  • the polyfunctional polymerizable compound preferably contains a polyfunctional polymerizable compound having a dipole moment of 3D or more (hereinafter also referred to as "polymerizable compound (Bx-3)"), and the polymerizable compound (Bx-3) is preferably a trifunctional polymerizable compound having a dipole moment of 3D or more, and more preferably a trifunctional (meth)acrylate compound having a dipole moment of 3D or more.
  • the dipole moment of the polymerizable compound (Bx-3) is preferably 3.2D or more, more preferably 3.4D or more, and even more preferably 3.6D or more.
  • the dipole moment of the polymerizable compound (Bx-3) is usually 10D or less, and may be 8.0D or less, 7.0D or less, 6.0D or less, 5.5D or less, 5.0D or less, or 4.0D or less.
  • the polymerizable compound (B) includes a polymerizable compound (Bx-3), and the polymerizable compound (Bx-3) is a trifunctional polymerizable compound having a dipole moment of 3D or more and 5D or less, or 3D or more and 4D or less.
  • the polymerizable compound (B) includes a polymerizable compound (Bx-2) and a polymerizable compound (Bx-3),
  • the polymerizable compound (Bx-2) is a bifunctional polymerizable compound having a dipole moment of 3D or more and 8D or less, or 3D or more and 7D or less
  • the polymerizable compound (Bx-3) is a trifunctional polymerizable compound having a dipole moment of 3D or more and 5D or less, or 3D or more and 4D or less.
  • the content thereof is preferably 0.1 mass% or more, more preferably 0.5 mass% or more, even more preferably 1.0 mass% or more, even more preferably 2.0 mass% or more, particularly preferably 3.0 mass% or more, particularly preferably 4.0 mass% or more, and most preferably 5.0 mass% or more, based on the total amount of the polymerizable compound (B), from the viewpoint of suppressing weight loss.
  • a polyfunctional polymerizable compound preferably, polymerizable compound (Bx-3)
  • the content thereof is preferably 0.1 mass% or more, more preferably 0.5 mass% or more, even more preferably 1.0 mass% or more, even more preferably 2.0 mass% or more, particularly preferably 3.0 mass% or more, particularly preferably 4.0 mass% or more, and most preferably 5.0 mass% or more, based on the total amount of the polymerizable compound (B), from the viewpoint of suppressing weight loss.
  • the content is preferably 20 mass% or less, more preferably 15 mass% or less, even more preferably 10 mass% or less, and even more preferably 8.0 mass% or less, based on the total amount of the polymerizable compound (B), from the viewpoint of reducing the viscosity of the curable composition.
  • the content thereof is preferably 0.1 mass% or more, more preferably 0.2 mass% or more, even more preferably 0.5 mass% or more, even more preferably 1.0 mass% or more, particularly preferably 2.0 mass% or more, particularly preferably 3.0 mass% or more, and most preferably 4.0 mass% or more, based on the total amount of the curable composition, from the viewpoint of suppressing weight loss.
  • a polyfunctional polymerizable compound preferably, polymerizable compound (Bx-3)
  • the content is preferably 15 mass% or less, more preferably 10 mass% or less, even more preferably 8.0 mass% or less, and even more preferably 6.0 mass% or less, based on the total amount of the curable composition, from the viewpoint of reducing the viscosity of the curable composition.
  • the polymerizable compound (B) may contain two or more types of polyfunctional polymerizable compounds (preferably, polymerizable compound (Bx-3)).
  • the above content of the polyfunctional polymerizable compound is the total content of two or more types of polyfunctional polymerizable compounds relative to the total amount of the polymerizable compound (B) and the total amount of the curable composition, respectively.
  • the polyfunctional polymerizable compound is preferably polymerizable compound (Bx-3).
  • the absolute value of the difference between the dipole moment of the polymerizable compound (Bx-2) and the dipole moment of the polymerizable compound (Bx-3) is preferably 2.0 D or less, more preferably 1.5 D or less, and even more preferably 1.0 D or less.
  • the absolute value of the difference may be 0 D.
  • the polymerizable compound (B) may contain a polymerizable compound having a dipole moment of less than 3D (hereinafter also referred to as "polymerizable compound (By)").
  • the content of the polymerizable compound (By) is preferably 30 mass% or less, more preferably 25 mass% or less, even more preferably 20 mass% or less, still more preferably 15 mass% or less, particularly preferably 10 mass% or less, and most preferably 5 mass% or less, based on the total amount of the polymerizable compound (B).
  • the content may be 0 mass%, 1 mass% or more, 2 mass% or more, or 3 mass% or more.
  • the content of the polymerizable compound (By) is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, and even more preferably 5% by mass or less, based on the total amount of the curable composition.
  • the content may be 0% by mass, 1% by mass or more, 2% by mass or more, or 3% by mass or more.
  • the polymerizable compound (B) may contain two or more kinds of polymerizable compounds (By).
  • the above content of the polymerizable compound (By) is the total content of two or more kinds of polymerizable compounds (By) relative to the total amount of the polymerizable compound (B) and the total amount of the curable composition, respectively.
  • the dipole moment of the polymerizable compound (By) may be, for example, 2.8 D or less, 2.5 D or less, or 2.0 or less, and may be greater than 0 or 0.0001 D or more.
  • the curable composition contains a polymerization initiator (C).
  • the polymerization initiator (C) 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 (B).
  • the curable composition may contain one or more polymerization initiators (C). Examples of the polymerization initiator (C) include photopolymerization initiators such as oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine compounds, and thermal polymerization initiators such as azo compounds and organic peroxides.
  • an oxime compound is an oxime compound having a first molecular structure represented by the following formula (1).
  • this oxime compound is also referred to as "oxime compound (1).”
  • Including oxime compound (1) as polymerization initiator (C) can be advantageous from the viewpoint of improving the luminescence intensity of the curable composition and the cured film.
  • One of the reasons for this effect is presumably that the absorption wavelength of oxime compound (1) changes significantly before and after the cleavage (decomposition) of oxime compound (1), which is necessary for oxime compound (1) to initiate photopolymerization, due to the unique molecular structure of oxime compound (1), and therefore oxime compound (1) has a high photoradical polymerization initiation ability.
  • R 1 represents R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN.
  • R 11 , R 12 and R 13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
  • the hydrogen atoms of the groups represented by R 11 , R 12 or R 13 may be substituted by OR 21 , COR 21 , SR 21 , NR 22 Ra 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , CN, a halogen atom or COOR 21 .
  • R 21 , R 22 and R 23 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
  • the hydrogen atom of the group represented by R 21 , R 22 or R 23 may be substituted by CN, a halogen atom, a hydroxy group or a carboxy group.
  • the alkylene portion may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
  • 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.
  • R 11 , R 12 , R 13 , R 21 , R 22 or R 23 has an alkyl portion
  • the alkyl portion may be branched or cyclic, and R 12 and R 13 , and R 22 and R 23 may be joined together to form a ring.
  • * 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.
  • Examples of the alkyl group having 1 to 20 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) 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 te
  • Examples of the aryl group having 6 to 30 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) 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.
  • Examples of the aralkyl group having 7 to 30 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) include a benzyl group, an ⁇ -methylbenzyl group, an ⁇ , ⁇ -dimethylbenzyl group, and a phenylethyl group.
  • Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) 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 preferably a 5- to 7-membered heterocyclic ring.
  • R 12 and R 13 , and R 22 and R 23 may each be joined together to form a ring, which means that R 12 and R 13 , and R 22 and R 23 may each be joined together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are connected.
  • Examples of the ring that can be formed by Ra 12 and Ra 13 together and Ra 22 and Ra 23 together in formula (1) 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 are preferably 5- to 7-membered rings.
  • halogen atom which may be contained as a substituent in R 11 , R 12 , R 13 , R 21 , R 22 and R 23 in the formula (1) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • R 1 in formula (1) is preferably R 11 , 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.
  • 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 that the oxime compound (1) has.
  • 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.
  • R2 and R3 each independently represent R11 , OR11 , SR11 , COR11 , CONR12R13 , NR12COR11 , OCOR11 , COOR11 , SCOR11 , OCSR11 , COSR11 , CSOR11 , CN or a halogen atom.
  • R2s When multiple R2s are present, they may be the same or different.
  • R3 's are present, they may be the same or different.
  • R 11 , R 12 and R 13 have the same meanings as above.
  • s and t each independently represent an integer of 0 to 4.
  • L represents a sulfur atom, CR 31 R 32 , CO or NR 33 .
  • R 31 , R 32 and R 33 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms.
  • the alkyl portion may be branched or cyclic, and R 31 , R 32 and R 33 may each independently form a ring together with either of the adjacent benzene rings.
  • R 4 is a hydroxy group, a carboxy group, or a group represented by the following formula (2-1):
  • L 1 represents —O—, —S—, —NR 22 —, —NR 22 CO—, —SO 2 —, —CS—, —OCO— or —COO—.
  • R22 has the same meaning as above.
  • L2 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.
  • the alkylene portion may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 22 -, -NR 22 COO-, -OCONR 22 -, -SCO-, -COS-, -OCS- or -CSO-, and the alkylene portion may be branched or cyclic.
  • R 4a represents OR 41 , SR 41 , CONR 42 R 43 , NR 42 COR 43 , OCOR 41 , COOR 41 , SCOR 41 , OCSR 41 , COSR 41 , CSOR 41 , CN or a halogen atom.
  • R 41 , R 42 and R 43 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms.
  • R 41 , R 42 and R 43 have an alkyl portion, the alkyl portion may be branched or cyclic, and R 42 and R 43 may be joined together to form a ring.
  • v represents an integer of 1 to 3. It represents a group represented by the following formula: * represents a bond to the first molecular structure of the oxime compound (1).
  • 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 represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 24 , R 31 , R 32 and R 33 in formula ( 2), and R 22 , R 41 , R 42 and R 43 in formula (2-1) above, are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1).
  • Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , and R 24 in formula (2), and R 22 in formula (2-1) above, are the same as the examples of R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , and R 24 in formula (1).
  • R 31 , R 32 and R 33 may each independently form a ring together with either of the adjacent benzene rings, which means that R 31 , R 32 and R 33 may each independently form a ring together with either of the adjacent benzene rings and the nitrogen atom to which they are connected.
  • Examples of the ring that R 31 , R 32 and R 33 in formula (2) may form together with either adjacent benzene ring are the same as the examples of the ring that Ra 12 and Ra 13 , and Ra 22 and Ra 23 in formula (1) may form together.
  • L2 in the above formula (2-1) 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.
  • Examples of groups in which v hydrogen atoms have been removed 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.
  • alkylene groups such as methylene, ethylene, propylene, methylethylene, butylene, 1-methylpropylene, 2-methyl
  • Examples of groups 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 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 2,6-naphthylene group, 1,4-naphthylene group, 2,5-dimethyl-1,4-phenylene group, diphenylmethane-4,4'-diyl group, 2,2-diphenylpropane-4,4'-diyl group, diphenylsulfide-4,4'-diyl group, and diphenylsulfone-4,4'-diyl group.
  • arylene groups such as 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 2,6-naphthylene group, 1,4-naphthylene group, 2,5-dimethyl-1,4-phenylene group, diphenyl
  • Examples of groups in which v hydrogen atoms have been removed from an aralkyl group having 7 to 30 carbon atoms, when v is 1, include groups represented by the following formula (a) and groups represented by the following formula (b).
  • L3 and L5 represent an alkylene group having 1 to 10 carbon atoms
  • L4 and L6 represent a single bond or an alkylene group having 1 to 10 carbon atoms.
  • alkylene groups having 1 to 10 carbon atoms include 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, and decylene.
  • Examples of groups in which v hydrogen atoms have been removed from a heterocyclic group having 2 to 20 carbon atoms, when v is 1, include divalent heterocyclic groups such as 2,5-pyridinediyl group, 2,6-pyridinediyl group, 2,5-pyrimidinediyl group, 2,5-thiophenediyl group, 3,4-tetrahydrofurandiyl group, 2,5-tetrahydrofurandiyl group, 2,5-furandiyl group, 3,4-thiazolediyl group, 2,5-benzofurandiyl group, 2,5-benzothiophenediyl group, N-methylindole-2,5-diyl group, 2,5-benzothiazolediyl group, and 2,5-benzoxazolediyl group.
  • divalent heterocyclic groups such as 2,5-pyridinediyl group, 2,6-pyridinediyl group, 2,5-pyrimidinediyl group, 2,
  • Examples of the halogen atom represented by R 2 and R 3 in formula (2) and R 4a in formula (2-1) above include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • a preferred example of the structure represented by formula (2) is the structure represented by the following formula (2a):
  • L' represents a sulfur atom or NR50
  • R50 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms
  • R2 , R3 , R4 , s and t are the same as defined above.
  • R 44 represents a hydroxy group, a carboxy group, or a group represented by the following formula (2-2):
  • L 11 represents -O- or *-OCO-
  • * represents a bond to L 12
  • L 12 represents an alkylene group having 1 to 20 carbon atoms which may be interrupted by 1 to 3 -O-
  • R 44a represents OR 55 or COOR 55
  • R 55 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 44 is preferably a group represented by formula (2-2). In this case, it is advantageous in terms of the solubility of the oxime compound (1) in the solvent (F) and the developability of the curable composition.
  • the alkylene group represented by L 12 preferably has 1 to 10 carbon atoms, and more preferably 1 to 4 carbon atoms.
  • R 44a is preferably a hydroxy group or a carboxy group, and more preferably a hydroxy group.
  • 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 2011-132215 A.
  • 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.
  • 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.
  • 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.
  • the alkyl moiety may be branched or cyclic.
  • R 21 , R 22 and R 23 have the same meanings as above.
  • the hydrogen atom of the group represented by R 21 , R 22 or R 23 may be substituted by CN, a halogen atom, a hydroxy group or a carboxy group.
  • the alkylene portion may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO- , -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
  • R 24 has the same meaning as above.
  • R 21 , R 22 and R 23 When the groups represented by R 21 , R 22 and R 23 have an alkyl portion, the alkyl portion may be branched or cyclic, and R 22 and R 23 may be joined together to form a ring.
  • R 6 , R 7 , R 8 and R 9 each independently represent R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN or a halogen atom.
  • R 61 , R 62 , R 63 , R 64 and R 65 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
  • the hydrogen atoms of the groups represented by R 61 , R 62 , R 63 , R 64 or R 65 may be substituted by OR 21 , COR 21 , SR 21 , NR 22 Ra 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 .
  • R 6 and R 7 , R 7 and R 8 , and R 8 and R 9 may each be joined together to form a ring. * represents a bond to the first molecular structure of the oxime compound (1).
  • 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 represented by R 5 , R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (3) include R 11 , The examples for R 12 , R 13 , R 21 , R 22 , R 23 and R 24 are similar.
  • R 22 and R 23 may be taken together to form a ring, which means that R 22 and R 23 may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are connected.
  • Examples of the ring which may be formed by R 22 and R 23 together in formula (3) are the same as the examples of the ring which may be formed by Ra 12 and Ra 13 , and Ra 22 and Ra 23 together in formula (1).
  • Examples of the halogen atoms which may replace the hydrogen atoms of the halogen atoms represented by R 6 , R 7 , R 8 and R 9 , and R 5 , R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (3) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • R 5 is a group represented by the following 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
  • the alkylene portion may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-, and the alkylene portion may be branched or cyclic.
  • R 21 , R 22 and R 24 have the same meanings as defined above.
  • Z in formula (3-1) is preferably a methylene group, ethylene or phenylene group.
  • R 21 and R 22 in formula (3-1) are preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, and more preferably a methyl group, an ethyl group, or a phenyl group.
  • R 7 is a nitro group.
  • 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, for example, by the methods described in JP-A-2000-80068 and JP-A-2011-178776.
  • 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.
  • 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 to each other.
  • 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.
  • the alkyl moiety may be branched or cyclic.
  • the hydrogen atom of the group represented by R 71 may be substituted by R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR 21 .
  • R 21 , R 22 and R 23 have the same meanings as defined above.
  • the hydrogen atom of the group represented by R 21 , R 22 or R 23 may be substituted by CN, a halogen atom, a hydroxy group or a carboxy group.
  • the alkylene portion may be interrupted 1 to 5 times by -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO- , -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
  • R 24 has the same meaning as above.
  • R 21 , R 22 and R 23 When the groups represented by R 21 , R 22 and R 23 have an alkyl portion, the alkyl portion may be branched or cyclic, and R 22 and R 23 may be joined together to form a ring.
  • R 72 , R 73 and the three R 74s each independently represent R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN or a halogen atom.
  • R 61 , R 62 , R 63 , R 64 and R 65 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
  • the hydrogen atoms of the groups represented by R 61 , R 62 , R 63 , R 64 or R 65 may be substituted by OR 21 , COR 21 , SR 21 , NR 22 Ra 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 .
  • R 72 and R 73 , and two R 74s may be joined together to form a ring. * represents a bond to the first molecular structure of the oxime compound (1).
  • 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 represented by R 71 , R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (4) are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1).
  • R 22 and R 23 may be taken together to form a ring, which means that R 22 and R 23 may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are connected.
  • Examples of the ring which R 22 and R 23 in formula (4) may form together are the same as the examples of the ring which Ra 12 and Ra 13 , and Ra 22 and Ra 23 in formula (1) may form together.
  • Examples of the halogen atoms which may replace the hydrogen atoms of the halogen atoms represented by R 72 , R 73 and R 74 , and R 71 , R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (4) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the method for producing the oxime compound (1) having the second molecular structure represented by formula (4) is not particularly limited, but it can be produced, for example, by the methods described in WO 2017/051680 and WO 2020/004601.
  • 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.
  • 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.
  • 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.
  • the alkyl moiety may be branched or cyclic.
  • the hydrogen atoms in the group represented by R 81 may be substituted by R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , a hydroxyl group, a nitro group, CN, a halogen atom, or COOR 21 .
  • R 21 , R 22 and R 23 have the same meanings as above.
  • the hydrogen atom of the group represented by R 21 , R 22 or R 23 may be substituted by CN, a halogen atom, a hydroxy group or a carboxy group.
  • the groups represented by R 21 , R 22 and R 23 have an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or - It may be interrupted 1 to 5 times by CSO-.
  • R 24 has the same meaning as above.
  • R 21 , R 22 and R 23 When the groups represented by R 21 , R 22 and R 23 have an alkyl portion, the alkyl portion may be branched or cyclic, and R 22 and R 23 may be joined together to form a ring.
  • R82 , R83 , R84 , R85 and R86 each independently represent R61 , OR61 , SR61, COR62 , CONR63R64 , NR65COR61 , OCOR61 , COOR62 , SCOR61 , OCSR61 , COSR62 , CSOR61 , a hydroxyl group , a nitro group, CN or a halogen atom.
  • R 61 , R 62 , R 63 , R 64 and R 65 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
  • the hydrogen atoms of the groups represented by R 61 , R 62 , R 63 , R 64 or R 65 may be substituted by OR 21 , COR 21 , SR 21 , NR 22 Ra 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 .
  • R 83 and R 84 , R 84 and R 85 , and R 85 and R 86 may each be joined together to form a ring. * represents a bond to the first molecular structure of the oxime compound (1).
  • 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 represented by R 81 , R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (5) are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1).
  • R 22 and R 23 may be taken together to form a ring, which means that R 22 and R 23 may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are connected.
  • Examples of the ring which may be formed by R 22 and R 23 together in formula (5) are the same as the examples of the ring which may be formed by Ra 12 and Ra 13 , and Ra 22 and Ra 23 together in formula (1).
  • Examples of the halogen atoms which may replace the hydrogen atoms of the halogen atoms represented by R82 , R83 , R84 , R85 and R86 , and R81 , R21 , R22 , R23 , R61 , R62 , R63 , R64 and R65 in formula (5) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the method for producing the oxime compound (1) having the second molecular structure represented by formula (5) is not particularly limited, but it can be produced, for example, by the methods described in WO 2017/051680 and WO 2020/004601.
  • 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.
  • 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.
  • the four R 91 , R 92 , R 93 , R 94 , R 95 , R 96 and R 97 each independently represent R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN or a halogen atom.
  • R 61 , R 62 , R 63 , R 64 and R 65 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
  • the hydrogen atoms of the groups represented by R 61 , R 62 , R 63 , R 64 or R 65 may be substituted by OR 21 , COR 21 , SR 21 , NR 22 Ra 23 , CONR 22 R 23 , -NR 22 -OR 23 , -N(COR 22 )-OCOR 23 , -C( ⁇ N-OR 21 )-R 22 , -C( ⁇ N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 .
  • R 21 , R 22 and R 23 have the same meanings as above.
  • R 92 and R 93 , R 94 and R 95 , R 95 and R 96 , and R 96 and R 97 may each be joined together to form a ring.
  • * represents a bond to the first molecular structure of the oxime compound (1).
  • 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 represented by R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (6) are the same as the examples for R 11 , R 12 , R 13 , R 21 , R 22 and R 23 in formula (1).
  • R 22 and R 23 may be taken together to form a ring, which means that R 22 and R 23 may be taken together to form a ring together with the nitrogen atom, carbon atom or oxygen atom to which they are connected.
  • Examples of the ring which may be formed by R 22 and R 23 together in formula (6) are the same as the examples of the ring which may be formed by Ra 12 and Ra 13 , and Ra 22 and Ra 23 together in formula (1).
  • halogen atoms which may replace the hydrogen atoms of the halogen atoms represented by R 91 , R 92 , R 93 , R 94 , R 95 , R 96 and R 97, and R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (6) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the method for producing the oxime compound (1) having the second molecular structure represented by formula (6) is not particularly limited, but it can be produced, for example, by the methods described in WO 2017/051680 and WO 2020/004601.
  • photopolymerization initiators include photopolymerization initiators other than the oxime compound (1).
  • Other photopolymerization initiators include oxime compounds other than the oxime compound (1), alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine compounds.
  • Oxime compounds other than oxime compound (1) include oxime compounds having a partial structure represented by the following formula (d1). * represents a bond.
  • 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]ethane-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-(3,3-dimethyl N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoy
  • the oxime compound having the 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, 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.
  • 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).
  • the benzene ring may have a substituent.
  • Examples of compounds having the 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, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one.
  • Commercially available products such as OMNIRAD (registered trademark) 369, 907, and 379 (all manufactured by IGM Resins) may also be used.
  • Examples of compounds having the 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, ⁇ , ⁇ -diethoxyacetophenone, and benzyl dimethyl ketal.
  • the alkylphenone compound is preferably a compound having a structure represented by formula (d2).
  • biimidazole compound is a compound represented by formula (d5).
  • R E to R J each represent 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 the like, with a phenyl group being preferred.
  • 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, and preferably a chlorine atom.
  • 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, and preferably a methoxy group.
  • biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-06-75372 and JP-A-06-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxy phenyl) biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl) biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trial
  • triazine compounds examples 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- Examples of the compound include [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-diethylamino-2-methylphen
  • acylphosphine compounds include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide.
  • Commercially available products such as OMNIRAD (registered trademark) 819 (manufactured by IGM Resins) may also be used.
  • photopolymerization initiators other than the oxime compound (1) include, for example, benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 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, benzyl, methyl phenylglyoxylate, and titan
  • the photopolymerization initiator is preferably at least one selected from the group consisting of an oxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, and an acylphosphine compound.
  • the photopolymerization initiator includes an acylphosphine oxide compound.
  • the content M of the polymerization initiator (C) is, for example, 0.1 mass% or more and 20 mass% or less based on the total amount of the curable composition. From the viewpoint of increasing the sensitivity of the curable composition and increasing the luminescence intensity and heat resistance (resistance to deterioration of luminescence characteristics due to heat) of the curable composition and the cured film, it is preferably 0.2 mass% or more and 15 mass% or less, more preferably 0.5 mass% or more and 10 mass% or less, even more preferably 1 mass% or more and less than 10 mass%, and still more preferably 1 mass% or more. The content is preferably from 1 to 8% by mass, and may be 6% or less by mass, or 5% or less by mass.
  • the content of the polymerization initiator (C) is, for example, 0.1% by mass or more and 20% by mass or less, based on the total amount of solids in the curable composition. From the viewpoint of increasing the sensitivity of the curable composition and increasing the luminescence intensity and heat resistance of the curable composition and the cured film, the content is preferably 0.2% by mass or more and 15% by mass or less, more preferably 0.5% by mass or more and 10% by mass or less, even more preferably 1% by mass or more and less than 10% by mass, still more preferably 1% by mass or more and 9% by mass or less, particularly preferably 1% by mass or more and 8% by mass or less, and may be 6% by mass or less or 5% by mass or less.
  • the curable composition may further contain a polymerization initiation aid (C1) together with the polymerization initiator (C).
  • the polymerization initiation aid (C1) is a compound used to promote the polymerization of the polymerizable compound (B) initiated by the polymerization initiator (C), or a sensitizer.
  • Examples of the polymerization initiation aid (C1) include photopolymerization initiation aids such as amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds, and thermal polymerization initiation aids.
  • the curable composition may contain two or more polymerization initiation aids (C1).
  • amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone.
  • alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
  • thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
  • carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc.
  • the content of the polymerization initiation aid (C1) 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, per 100 parts by mass of the polymerizable compound (B).
  • the content of the polymerization initiation aid (C1) is within the above range, the curable composition can be made even more sensitive.
  • the curable composition contains an antioxidant (D).
  • the antioxidant (D) is not particularly limited as long as it is an antioxidant generally used industrially, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, etc. can be used.
  • the curable composition may contain two or more types of antioxidants (D).
  • phenol-based antioxidants examples 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)propionate, manufactured by BASF Corporation), and Irganox 1330 (Irganox 1330: 3,3',3'',5,5',5''-hexa-tert-butyl-
  • Irganox 3114 Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Co., Ltd.
  • 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 Co., Ltd.
  • Irganox 1035 Irganox 1035: thiodiethylenebis[3-(3,5-di-tert t-butyl-4-hydroxyphenyl)propionate, manufactured by BASF Corporation
  • Irganox 1135 Irganox 1135:
  • phenol-based antioxidant an antioxidant having a hindered phenol structure in which a bulky organic group is bonded to at least one ortho position of a phenolic hydroxy group is preferred.
  • a secondary or tertiary alkyl group is preferred, and specific examples include an isopropyl group, an s-butyl group, a t-butyl group, an s-amyl group, and a t-amyl group.
  • a tertiary alkyl group is preferred, and a t-butyl group or a t-amyl group is particularly preferred.
  • 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), and Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Corporation).
  • Irgafos registered trademark
  • Irgafos 168 tris(2,4-di-tert-butylphenyl)phosphi
  • an antioxidant having a group represented by the following formula (e1) is preferable.
  • R e1 to R e5 each independently represent a hydrogen atom or an alkyl group, and * represents a bond.
  • R e1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom, a methyl group, an ethyl group, or a t-butyl group.
  • R e2 and R e4 are preferably a methyl group or a hydrogen atom, and more preferably a hydrogen atom.
  • R e5 and R e3 are each preferably an alkyl group, more preferably a secondary or tertiary alkyl group, and even more preferably a t-butyl group or a t-amyl group.
  • the two units enclosed in parentheses may be bonded together via R e1 to form a ring.
  • Bonding via R e1 refers to a mode in which groups obtained by removing a hydrogen atom from R e1 are bonded together, and for example, when both R e1 are hydrogen atoms, this refers to a mode in which the carbon atom to which R e1 is bonded in one benzene ring and the carbon atom to which R e1 is bonded in the other benzene ring are directly bonded together.
  • Sulfur-based antioxidants include, for example, dialkyl thiodipropionate compounds such as dilauryl, dimyristyl, or distearyl thiodipropionate, and ⁇ -alkyl mercaptopropionate compounds of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane.
  • the antioxidant (D) is preferably a phenol-based antioxidant or a phosphorus-based antioxidant, more preferably an antioxidant having at least one of the above hindered phenol structure and a group represented by formula (e1), even more preferably an antioxidant having both the above hindered phenol structure and a group represented by formula (e1), and particularly preferably Sumilizer (registered trademark) GP.
  • the content M of the antioxidant (D) is, for example, 0.01 mass% or more and 60 mass% or less, relative to the total amount of the curable composition. From the viewpoint of increasing the luminous intensity and heat resistance (resistance to deterioration of luminous properties due to heat) of the curable composition and the cured film, the content M of the antioxidant (D) is preferably 0.1 mass% or more and 50 mass% or less, more preferably 0.2 mass% or more and 40 mass% or less, and even more preferably 0.5 mass% or more and 30 mass% or less, and may be 20 mass% or less, 10 mass% or less, 5 mass% or less, or 2 mass% or less.
  • the content of the antioxidant (D) is, for example, 0.01% by mass or more and 60% by mass or less, based on the total amount of solids in the curable composition. From the viewpoint of increasing the luminescence intensity and heat resistance of the curable composition and the cured film, the content is preferably 0.1% by mass or more and 50% by mass or less, and more preferably 0.2% by mass or more. The content is preferably from 0.5 to 30% by mass, and may be 20% by mass or less, 10% by mass or less, 5% by mass or less, or 2% by mass or less.
  • the curable composition may further include a light scattering agent (E).
  • a light scattering agent E
  • the curable composition may include two or more kinds of light scattering agents (E).
  • Examples of the light scattering agent (E) include inorganic particles such as metal or metal oxide particles, glass particles, etc.
  • metal oxides include TiO 2 , SiO 2 , BaTiO 3 , ZnO, etc., and TiO 2 particles are preferred because they scatter light efficiently.
  • the volume-based median diameter of the light scattering agent (E) is, for example, 0.03 ⁇ m or more, preferably 0.10 ⁇ m or more, more preferably 0.15 ⁇ m or more, and even more preferably 0.20 ⁇ m or more, and is, for example, 20 ⁇ m or less, preferably 5 ⁇ m or less, and even more preferably 1 ⁇ m or less.
  • the content of the light scattering agent (E) in the curable composition is, for example, 0.001% by mass or more and 50% by mass or less based on the total amount of the curable composition or the total amount of solids in the curable composition, and from the viewpoint of improving the light scattering ability and luminescence intensity of the curable composition and the cured film, it is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 1% by mass or more, and is preferably 30% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less.
  • the curable composition may contain a solvent (F), but when the solvent (F) is contained, the content is preferably low.
  • the content is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, even more preferably 2% by mass or less, particularly preferably 1% by mass or less, and may be 0% by mass or more, based on the total amount of the curable composition.
  • Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and gamma-butyrolactone.
  • Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.
  • Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, Examples of such ethers include ethyl
  • 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.
  • Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
  • Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
  • Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
  • the solvent (F) is preferably an ester solvent, an ether ester solvent, an alcohol solvent, or an amide solvent, and more preferably an ether ester solvent.
  • Leveling agent (H) The curable composition may further include a leveling agent (H).
  • a leveling agent (H) examples include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain.
  • the curable composition may include two or more types of leveling agents (H).
  • 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 (product names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).
  • Fluorosurfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (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 Chemicals Research Institute, Ltd.).
  • Fluorad registered trademark
  • FC430 and FC431 manufactured by Sumitomo 3M Limited
  • Megafac registered trademark
  • silicone surfactants containing fluorine atoms include surfactants that have siloxane bonds and fluorocarbon chains in the molecule. Specific examples include Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).
  • 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, more preferably 0.01 mass% or more and 0.5 mass% or less, and even more preferably 0.05 mass% or more and 0.5 mass% or less, relative to the total amount of the curable composition.
  • the content of the leveling agent (H) is within the above range, the flatness of the cured film can be improved.
  • the curable composition may contain a resin (I), but when the curable composition contains a resin (I), the content is preferably low.
  • the content is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, even more preferably 2% by mass or less, particularly preferably 1% by mass or less, and may be 0% by mass or more, based on the total amount of the curable composition.
  • Resin [K1] a copolymer of at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter also referred to as “(a)”) and a monomer (c) (different from (a)) copolymerizable with (a) (hereinafter also referred to as “(c)”);
  • Resin [K2] a resin obtained by reacting a copolymer of (a) and (c) with a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter also referred to as "(b)”);
  • Resin [K3] a resin obtained by reacting a copolymer of (b) and (c) with (a);
  • Resin [K4] A resin obtained by reacting a copolymer of (b)
  • 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
  • (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.
  • Examples of (b) include glycidyl (meth)acrylate, ⁇ -methyl glycidyl (meth)acrylate, ⁇ -ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, and the like.
  • monomers having an oxirane ring and an ethylenically unsaturated bond such as 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; Monomers having an oxetane ring and an ethylenically unsaturated bond, such as 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethylox
  • a monomer having an oxirane ring and an ethylenically unsaturated bond is preferred as (b) since the reactivity during the production of Resins [K2] to [K4] is high and unreacted (b) is unlikely to remain.
  • 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”).
  • (meth)acrylic acid esters such as decene-8-yl (meth)acrylate (commonly known in the art as "dicyclopentenyl (meth)acrylate"), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, 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-
  • styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are preferred from the viewpoints of copolymerization reactivity and heat resistance of the resin (C).
  • the structural units derived from (a) are preferably from 2 mol % to 60 mol %.
  • the structural units derived from (c) are preferably from 40 mol % to 98 mol %. More preferably, the structural units derived from (a) are from 10 mol % to 50 mol % and the structural units derived from (c) are from 50 mol % to 90 mol %.
  • the resin (I) when the resin (I) contains a structural unit derived from (a), it may contain two or more structural units derived from (a), and in this case, the ratio (molar content) of the structural unit derived from (a) is the sum of the ratios of each structural unit.
  • the structural units derived from other monomers such as (b) and (c).
  • Resin [K1] can be produced, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis” (written by Otsu Takayuki, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and the references cited in said literature.
  • a method 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 made deoxygenated, for example, by replacing oxygen with nitrogen, and the mixture is heated and kept warm while being stirred, can be mentioned.
  • the polymerization initiator and solvent used are not particularly limited, and those generally used in the relevant field can be used.
  • the polymerization initiator can be an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer, and can be the solvents described above as the solvent (F) that may be contained in the curable composition.
  • the resulting copolymer may be used as is in the form of a solution after the reaction, or in a concentrated or diluted form, or extracted as a solid (powder) by a method such as reprecipitation.
  • Resin [K2] 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).
  • a copolymer of (a) and (c) is produced in the same manner as described for the production method of resin [K1].
  • the ratio of the structural units derived from each is preferably the same as that described for resin [K1].
  • the amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a).
  • organic phosphorus compound used as a reaction catalyst for example, triphenylphosphine can be used.
  • an amine compound used as a reaction catalyst for example, an aliphatic tertiary amine compound or an aliphatic quaternary ammonium salt compound can be used, and specific examples thereof include tris(dimethylaminomethyl)phenol, triethylamine, tetrabutylammonium bromide, and tetrabutylammonium chloride.
  • 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).
  • 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).
  • the reaction conditions such as the charging method, reaction temperature and time can be adjusted as appropriate, taking into consideration the production equipment, the amount of heat generated by polymerization, etc.
  • the charging method and reaction temperature can be adjusted as appropriate, taking into consideration the production equipment, the amount of heat generated by polymerization, etc.
  • resin [K3] is produced by obtaining a copolymer of (b) and (c) in the same manner as in the production method of resin [K1] described above.
  • the obtained copolymer may be used as it is in the form of a solution after the reaction, or a concentrated or diluted solution, or it may be extracted as a solid (powder) by a method such as reprecipitation.
  • the ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are, respectively,
  • the structural units derived from (b) are preferably from 5 mol % to 95 mol %.
  • the structural units derived from (c) are preferably from 5 mol % to 95 mol %.
  • the structural units derived from (b) are more preferably from 10 mol % to 90 mol %.
  • the structural units derived from (c) are more preferably from 10 mol % to 90 mol %.
  • Resin [K3] 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 [K2].
  • the amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b).
  • Resin [K4] is a resin obtained by further reacting resin [K3] with a carboxylic acid anhydride. A 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.
  • carboxylic acid anhydrides examples 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.
  • the amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.
  • Examples of the resin [K1], the resin [K2], the resin [K3] and the resin [K4] include resin [K1] such as a benzyl (meth)acrylate/(meth)acrylic acid copolymer and a styrene/(meth)acrylic acid copolymer; Resins [K2] such as a resin obtained by adding glycidyl (meth)acrylate to a benzyl (meth)acrylate/(meth)acrylic acid copolymer, a resin obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, and a resin obtained by adding glycidyl (meth)acrylate to a tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer; Resins [K3] such as
  • resin (I) examples include the resins described in JP 2018-123274 A.
  • examples of the resin include a polymer (hereinafter also referred to as "resin (Ba)") having a double bond in a side chain, containing a structural unit ( ⁇ ) represented by the following formula (I) and a structural unit ( ⁇ ) represented by the following formula (II) in the main chain, and further containing an acid group.
  • the acid group can be introduced into the resin (Ba) by, for example, including a structural unit ( ⁇ ) derived from an acid group-containing monomer (e.g., (meth)acrylic acid, etc.).
  • the resin (Ba) preferably includes the structural units ( ⁇ ), ( ⁇ ) and ( ⁇ ) in the main chain skeleton.
  • 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.
  • R C may be the same or different and represent a hydrogen atom or a methyl group.
  • R D may be 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 more.
  • the content of structural unit ( ⁇ ) is, for example, from 0.5% by mass to 50% by mass, preferably from 1% by mass to 40% by mass, and more preferably from 5% by mass to 30% by mass, relative to 100% by mass of the total amount of all monomer units that provide the main chain skeleton of resin (Ba), from the viewpoint of the heat resistance and storage stability of resin (Ba).
  • n in formula (I) represents the average number of repeating units of structural unit ( ⁇ ) in resin (Ba), and n can be set so that the content of structural unit ( ⁇ ) is within the above range.
  • the content of the structural unit ( ⁇ ) 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 provide the main chain skeleton of the resin (Ba).
  • m in formula (II) represents the average number of repeating units of the structural unit ( ⁇ ) in the resin (Ba), and m can be set so that the content of the structural unit ( ⁇ ) falls within the above-mentioned range.
  • the content of the structural unit ( ⁇ ) is, for example, from 0.5% by mass to 50% by mass, preferably from 2% by mass to 50% by mass, and more preferably from 5% by mass to 45% by mass, relative to 100% by mass of the total amount of all monomer units that provide the main chain structure of the resin (Ba), from the viewpoint of the solubility of the resin (Ba), etc.
  • Resin (I) may be one or more selected from the group consisting of the above-mentioned resins [K1], [K2], [K3], [K4] and (Ba).
  • the curable composition may contain additives such as a dispersant, a plasticizer, and a filler as other components, as necessary.
  • Dispersants include, but are not limited to, cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. Dispersants are preferably used in combination with the curable composition when it contains a light scattering agent (E). When the curable composition contains a dispersant, the dispersibility of the light scattering agent (E) in the curable composition is improved.
  • the content of the dispersant is preferably 10 mass% or less, more preferably 5 mass% or less, even more preferably 3 mass% or less, and particularly preferably 1 mass% or less, relative to the total amount of the curable composition. It may also be 0 mass%, 0.1 mass% or more, or 0.3 mass% or more. From the viewpoint of reducing viscosity, it is preferably 3 mass% or less, more preferably 2 mass% or less, and particularly preferably 1 mass% or less.
  • the content of the additives is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, and particularly preferably 1% by mass or less, relative to the total amount of the curable composition, and may be 0% by mass.
  • the curable composition can be prepared by a method including a step of mixing the prescribed components and other components that are used as required.
  • the order in which the components are mixed is not particularly limited, but for example, the semiconductor particles (A) and the polymerizable compound (B) can be mixed to obtain a dispersion, and then the dispersion can be mixed with the polymerization initiator (C), the antioxidant (D) and other components to prepare the curable composition.
  • the ligand-containing semiconductor particles as the semiconductor particles (A) may be, for example, semiconductor particles to which organic ligands are coordinated, which are then prepared and subjected to a ligand reduction treatment to reduce the amount of the organic ligands coordinated to the semiconductor particles.
  • the ligand reduction treatment may be, for example, a treatment to extract the organic ligands coordinated to the semiconductor particles into an appropriate solvent.
  • the viscosity of the curable composition at 40°C is preferably 20 cP or less, more preferably 15 cP or less, even more preferably 12 cP or less, and even more preferably 10 cP or less. There is no particular lower limit, but it may be 2 cP or more, 3 cP or more, or 5 cP or more.
  • the curable composition When used as an ink for an inkjet printer, the curable composition can be ejected from the ejection head of the inkjet printer at a temperature of 40°C or higher. Since the curable composition can have good heat resistance, even when the curable composition is ejected under conditions where the temperature of the curable composition is 40°C or higher, the physical properties (particularly the light conversion efficiency) of the resulting cured film can be good.
  • the temperature of the curable composition when ejected from the ejection head of the inkjet printer can be 50°C or higher, 60°C or higher, or 80°C or lower.
  • a cured film can be obtained by curing a film (layer) made of a curable composition. Specifically, the curable composition is applied onto a substrate to form a coating film, and the resulting coating film is exposed to light to obtain a cured film.
  • 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, polymethylmethacrylate, and polyethylene terephthalate, silicon, and the above substrates on which thin films of aluminum, silver, and silver/copper/palladium alloys have been formed can be used.
  • various printing methods such as gravure printing, offset printing, letterpress printing, screen printing, transfer printing, electrostatic printing, and plateless printing
  • coating methods such as gravure coating, roll coating, knife coating, air knife coating, bar coating, dip coating, kiss coating, spray coating, die coating, comma coating, inkjet printing, spin coating, and slit coating, or combinations of these methods can be used as appropriate.
  • 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. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges.
  • Examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. Exposure may be performed in an air atmosphere or an inert gas (nitrogen, argon, etc.) atmosphere, but is preferably performed in an inert gas atmosphere.
  • a patterned cured film can be formed from the curable composition by patterning using a method such as photolithography, inkjet printing, or printing. Note that photolithography results in loss of expensive composition materials, so from the viewpoint of reducing material loss, it is preferable to employ the inkjet method.
  • An example of a method for producing a patterned cured film by the inkjet method is to form a bank on a substrate, and then selectively apply a curable composition to the area on the substrate partitioned by the bank by the inkjet method, and then cure the curable composition by exposure to light.
  • the substrate may be any of the substrates exemplified in the description of the method for producing a cured film above.
  • Methods for forming the bank include photolithography and inkjet methods, and it is preferable to form the bank by the inkjet method.
  • the inkjet method include the bubble jet (registered trademark) method, which uses an electrothermal converter as an energy generating element, or the piezojet method, which uses a piezoelectric element.
  • the light source used for exposure can be any of the light sources exemplified in the description of the method for producing the cured film above.
  • the unpatterned or patterned cured film can be suitably used as a wavelength conversion film (wavelength conversion filter) that emits light with a wavelength different from the wavelength of light incident from a light emitting unit such as an LED.
  • the patterned cured film is preferably positioned above a light emitting element such as an LED that corresponds to each pattern.
  • a light emitting element such as an LED that corresponds to each pattern.
  • FIG. 1 is a schematic cross-sectional view of one embodiment of a display member formed by an inkjet method.
  • the display member 10 in Figure 1 has banks 2 formed on a substrate 1 and light-emitting elements 3 such as LEDs installed between the banks 2, and has a cured film 4 (wavelength conversion film) obtained by applying the curable composition according to the present invention by an inkjet method onto the light-emitting elements 3 between the banks 2 and then curing the composition (hereinafter, each cured film patterned to the size between the banks 2 is also referred to as a "cured film pixel").
  • a color filter 5, a gas barrier layer 6, etc. may be disposed on each cured film pixel 4.
  • the cured film pixels 4 By forming the cured film pixels 4 using the inkjet method, it becomes possible to pattern them in relatively large sizes, making them ideal for use in large displays such as digital signage.
  • the vertical dimension (L1) of the cured film pixel 4 formed from the curable composition according to the present invention is preferably 9 ⁇ m or more, more preferably 12 ⁇ m or more, and even more preferably 15 ⁇ m or more, and may be 40 ⁇ m or less, or may be 30 ⁇ m or less.
  • the vertical dimension (L1) may be the same length as the horizontal dimension (L3) of the light-emitting element.
  • the horizontal dimension (L2) of the cured film pixel 4 formed from the curable composition of the present invention is preferably 10 ⁇ m or more, more preferably 30 ⁇ m or more, even more preferably 50 ⁇ m or more, even more preferably 80 ⁇ m or more, and particularly preferably 100 ⁇ m or more, and may be 900 ⁇ m or less, 800 ⁇ m or less, or 700 ⁇ m or less.
  • the vertical dimension (L1) of the cured film pixel 4 is the dimension in the thickness direction of the substrate in a cross section cut in a direction perpendicular to the substrate.
  • the cross section is cut at a location where the vertical dimension of the cured film pixel 4 is maximum.
  • FIG. 1 shows a cross section cut in a direction perpendicular to the substrate at a location where the vertical dimension of the cured film pixel 4 is maximum.
  • the horizontal dimension (L2) of the cured film pixel 4 is the maximum dimension of the cured film pixel 4 in a direction horizontal to the substrate, and refers to the dimension when the substrate is viewed from the vertical direction (planar dimension).
  • the horizontal dimension (L3) of the light-emitting element is the maximum dimension of the light-emitting element in a direction horizontal to the substrate, and refers to the dimension when the substrate is viewed from the vertical direction (planar dimension).
  • Dipole moment of polymerizable compound The dipole moment (D: Debye) of a polymerizable compound is determined based on its molecular structure as follows: The values were determined by DFT (Density Functional Theory; B3LYP/6-31G+g(d)) calculations using the quantum chemical calculation program "Gaussian 16" manufactured by NKS. The results are shown in Table 1.
  • Viscosity of the curable composition 40°C
  • the viscosity (cP) of the cured composition at 40° C. was measured using a Brookfield rotational viscometer at a constant temperature of 40° C. and a rotation speed of 7 rpm. The results are shown in Table 1.
  • Luminescence Intensity of Cured Film A cured film was prepared on a glass substrate in the same manner as in (5) above. A light diffusion plate was placed on a backlight using a blue LED lamp with a peak emission wavelength of 450 nm as a point light source to form a backlight unit. The backlight unit was placed with the light diffusion plate facing upward, and a spectroradiometer (SR-UL1R manufactured by Topcon Corporation) was installed at a height of 60 cm from the surface of the light diffusion plate. The cured film formed on the glass substrate was used as a measurement sample, and the measurement sample was placed on the surface of the light diffusion plate with the cured film facing upward.
  • SR-UL1R spectroradiometer
  • Semiconductor particles (A1) A quantum dot dry product obtained by removing toluene by reduced pressure distillation from a toluene dispersion of a ligand-containing quantum dot having an InP/ZnSeS structure (maximum peak wavelength of emission spectrum: 530 nm, full width at half maximum: 42 nm) containing an organic ligand (G) which is oleic acid.
  • the emission spectrum of the semiconductor particles (A1) was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics "C9920-02", excitation light 450 nm, room temperature, in air) using a semiconductor particle (A) dispersion diluted to an absorbance of 0.4 at a wavelength of 450 nm as the measurement sample.
  • Examples 1 to 9 and Comparative Examples 1 to 3 The polymerizable compound (B) shown in Table 1 was added to the semiconductor particles (A) and stirred with an ultrasonic cleaner and a touch mixer until the solid matter disappeared, to obtain a quantum dot monomer dispersion.
  • the polymerization initiator (C) and the antioxidant (D) were added to the obtained dispersion so as to obtain the composition shown in Table 1, and the mixture was stirred with a touch mixer to obtain a curable composition.
  • Table 1 the parts of each component are shown as solid content equivalents.
  • Substrate 2. Bank, 3. Light-emitting element, 4. Cured film (wavelength conversion film), 5. Color filter, 6. Gas barrier layer, 10. Display member, L1. Vertical dimension, L2. Horizontal dimension, L3. Horizontal dimension of light-emitting element.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Polymerisation Methods In General (AREA)
  • Luminescent Compositions (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

L'invention concerne une composition durcissable qui contient des particules semi-conductrices (A), des composés polymérisables (B), un initiateur de polymérisation (C) et un antioxydant (D). Les composés polymérisables (B) comprennent, en une quantité supérieure ou égale à 40 % en masse par rapport à la quantité totale des composés polymérisables (B), un composé polymérisable ayant un moment dipolaire dans au moins 3 dimensions.
PCT/JP2023/034842 2022-10-20 2023-09-26 Composition durcissable, film durci et dispositif d'affichage WO2024084904A1 (fr)

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