Composition and cured product thereof, molding, display unit and solid state imaging device

Abstract

To provide a composition containing a compound having at least one of a thiirane group or a thietane group, the composition imparting a cured product excellent in storage stability, curability and thermostability.SOLUTION: A composition includes: a compound (A) having one or more of a thiirane group or a thietane group; a compound (B) selected from a compound group having a skeleton of expression (I) or (II).SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a composition, a cured product thereof, a molded product, a display device, and a solid-state imaging device.

Background Art

[0002] In the field of optical devices, high refractive index materials are in demand. A lens can be obtained from a high refractive index material, and the optical path in the optical device can be controlled by the lens. A lens is used for the purpose of improving the light condensing efficiency on each photoelectric conversion element in a solid-state imaging device, and a lens is also used for the purpose of improving the light extraction efficiency from pixels in a display device. Conventionally, various high refractive index materials have been developed (for example, Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] When the present inventors conducted research on high refractive index materials, they found that a compound having at least one thiirane group or thietane group is useful as a high refractive index material. However, a composition containing such a compound or a cured product thereof does not satisfy high levels of curability, heat resistance, and storage stability, and there is still room for improvement.

[0005] Therefore, a main object of the present invention is to provide a composition that is excellent in storage stability and can give a cured product excellent in curability and heat resistance in a composition containing a compound having at least one thiirane group or thietane group.

Means for Solving the Problems

[0006] The present invention provides a composition described in [1] to [5], a molded article described in [6], a cured product described in [7], a display device described in [8], and a solid-state imaging device described in [9]. [1] A compound (A) having at least one thiirane group or thietane group, and at least one compound (B) selected from the group consisting of a compound having a skeleton represented by formula (I) and a salt thereof, and a compound having a skeleton represented by formula (II) and a salt thereof, A composition containing

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Advantages of the Invention

[0007] According to the present invention, there is provided a composition containing a compound having at least one thiirane group or thietane group, which has excellent storage stability and can provide a cured product having excellent curability and heat resistance. Further, according to the present invention, there are provided a molded article using such a composition, a cured product of such a composition, a display device including the cured product, and a solid-state imaging device including the cured product.

Embodiments for Carrying Out the Invention

[0008] Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.

[0009] In this specification, a numerical range indicated by "~" means a range including the numerical values described before and after "~" as the minimum value and the maximum value, respectively. In the numerical ranges described stepwise in this specification, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another numerically described range. Further, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.

[0010] In this specification, (meth)acrylate means acrylate or the corresponding methacrylate. The same applies to other similar expressions such as (meth)acryloyl group and (meth)acrylic acid ester.

[0011] In this specification, the materials exemplified below may be used alone or in combination of two or more within the range applicable to the conditions, unless otherwise specified. The content of each component means the total amount of the plurality of substances corresponding to each component, unless otherwise specified, when there are a plurality of substances corresponding to each component.

[0012] <Composition> The composition of one embodiment contains a compound (A) having at least one thiirane group or thietane group, at least one compound (B) selected from the group consisting of a compound having a skeleton represented by formula (I) and a salt thereof, and a compound having a skeleton represented by formula (II) and a salt thereof. According to the composition of this embodiment, it has excellent storage stability and can provide a cured product having excellent curability and heat resistance. The composition of this embodiment may further contain a polymerization inhibitor (C) or the like.

[0013] (A) component: Compound (A) The composition of this embodiment contains the (A) component. The (A) component can be a curable compound. By the composition containing the (A) component, it becomes possible for the (A) component to polymerize and give a cured product showing a high refractive index.

[0014] (A) component can be used without particular limitation as long as it is a compound having at least one thiirane group or thietane group. The (A) component may be, for example, a compound having at least one group represented by formula (X0), and preferably a compound having at least one group represented by formula (X1).

[0015] [Chemical formula]

[0016] In formula (X0), m represents 0 or 1. R 2 represents a hydrogen atom or a monovalent substituent. * represents the bonding position.

[0017] [Chemical formula]

[0018] In formula (X1), L represents a single bond or a divalent group. m represents 0 or 1. R 2represents a hydrogen atom or a monovalent substituent. * represents the bonding position.

[0019] Examples of the divalent group represented by L include a divalent aliphatic chain hydrocarbon group which may have a substituent; a divalent alicyclic hydrocarbon group which may have a substituent; a divalent aromatic hydrocarbon group which may have a substituent; a divalent hydrocarbon group composed of a combination thereof (for example, an aralkylene group), etc. The methylene group (-CH2-) contained in the divalent group may be substituted with -O-, -S-, -NR A -(R A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).), -CO-, or -SO2-.

[0020] Examples of the divalent aliphatic chain hydrocarbon group include a saturated or unsaturated aliphatic chain hydrocarbon group. More specifically, alkane diyl groups such as methylene group, ethylene group, propane diyl group, butane diyl group, pentane diyl group, hexane diyl group, heptane diyl group, octane diyl group, nonane diyl group, decane diyl group, undecane diyl group, dodecane diyl group, tridecane diyl group, tetradecane diyl group, pentadecane diyl group, hexadecane diyl group, heptadecane diyl group, octadecane diyl group, nonadecane diyl group, eicosane diyl group, etc. The divalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms of the divalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0021] Examples of the substituent which the divalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group, etc.

[0022] Examples of the divalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, monocyclic alicyclic hydrocarbon groups such as cyclopropanediyl group, cyclobutanediyl group, cyclopentanediyl group, cyclohexanediyl group, cyclooctanediyl group, cyclononanediyl group, cyclodecanediyl group; polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butanediyl group, tricyclo[2.2.1.0]heptanediyl group, bicyclo[3.2.1]octanediyl group, bicyclo[2.2.2]octanediyl group, adamantanediyl group, bicyclo[4.3.2]undecanediyl group, tricyclo[5.3.1.1]dodecanediyl group, etc. are included. The number of carbon atoms of the divalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, and even more preferably 5 or 6.

[0023] Examples of the substituent that the divalent alicyclic hydrocarbon group may have include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group, etc.

[0024] The divalent aromatic hydrocarbon group may be monocyclic or polycyclic. Examples of the divalent aromatic hydrocarbon group include phenylene group, naphthylene group, anthracenediyl group, fluorenediyl group, etc. The number of carbon atoms of the divalent aromatic hydrocarbon group is usually 6 to 20, preferably 6 to 10.

[0025] Examples of the substituent that the divalent aromatic hydrocarbon group may have include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group, etc.

[0026] R 2 Examples of the monovalent substituent represented by R include a monovalent aliphatic chain hydrocarbon group which may have a substituent, a monovalent alicyclic hydrocarbon group which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent group composed of a combination thereof (e.g., an aralkyl group), etc.; a monovalent heterocyclic group which may have a substituent; a hydroxy group; an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, a methylethylamino group, etc., an amino group which may be substituted with one or two alkyl groups having 1 to 6 carbon atoms; a halogen atom; a nitro group; a cyano group; a carboxy group; a sulfo group; a thiol group; a formyl group; a -SF3 group; a -SF5 group. The methylene group (-CH2-) contained in the monovalent substituent may be substituted with -O-, -S-, -NR B -(R B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.).), -CO-, or -SO2-. The group in which the methylene group (-CH2-) contained in the monovalent substituent is substituted with -O- includes alkoxy groups having 1 to 12 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group; and alkoxyalkyl groups such as a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, etc.

[0027] Examples of the monovalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, etc. The monovalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms of the monovalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0028] Examples of the substituent that the monovalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group and the like.

[0029] Examples of the monovalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, monocyclic alicyclic hydrocarbon groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, cyclononyl group, cyclodecyl group; polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butyl group, tricyclo[2.2.1.0]heptyl group, bicyclo[3.2.1]octyl group, bicyclo[2.2.2]octyl group, adamantyl group, bicyclo[4.3.2]undecyl group, tricyclo[5.3.1.1]dodecyl group and the like. The number of carbon atoms of the monovalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, and still more preferably 5 or 6.

[0030] Examples of the substituent that the monovalent alicyclic hydrocarbon group may have include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group and the like.

[0031] The monovalent aromatic hydrocarbon group may be monocyclic or polycyclic. Examples of the monovalent aromatic hydrocarbon group include phenyl group, naphthyl group, anthracenyl group, fluorenyl group and the like. The number of carbon atoms of the monovalent aromatic hydrocarbon group is usually 6 to 20, preferably 6 to 10.

[0032] Examples of the substituent that the monovalent aromatic hydrocarbon group may have include an alkyl group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; a halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; a hydroxy group; an amino group; an acetyl group; a cyano group and the like.

[0033] Examples of the monovalent heterocyclic group include an aliphatic heterocyclic group having 4 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms such as pyrrolidinyl group, pyrrolinyl group, imidazolidinyl group, imidazolinyl group, oxazolinyl group, thiazolyl group, piperidinyl group, morpholinyl group, piperazinyl group, indolyl group, isoindolyl group, quinolyl group, thienyl group, pyrrolyl group, furyl group and the like.

[0034] Examples of the substituent that the monovalent heterocyclic group may have include an alkyl group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; a halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; a hydroxy group; an amino group; an acetyl group; a cyano group and the like.

[0035] m represents 0 or 1. When m is 0, it represents a three-membered ring structure which is a thiirane group, and when m is 1, it represents a four-membered ring structure which is a thietane group. m is preferably 0.

[0036] From the viewpoint of the high refractive index of the cured product, the component (A) is preferably a compound containing an aromatic ring. Examples of the aromatic ring include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring; aromatic heterocyclic rings such as furan ring, pyrrole ring, benzofuran ring, thiophene ring, benzothiophene ring, indole ring, pyridine ring, quinoline ring, isoquinoline ring, pyridazine ring, pyrimidine ring, triazine ring and the like. The aromatic ring is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring.

[0037] Component (A) is preferably a compound represented by formula (A-1) (hereinafter sometimes referred to as "compound (A-1)") from the viewpoint of the high refractive index of the cured product.

[0038]

Chemical formula

[0039] In formula (A-1), L represents a single bond or a divalent group, and the two Ls may be the same or different. A 1 represents an oxygen atom or a sulfur atom, and the two As 1 may be the same or different. However, at least one of the two As 1 is a sulfur atom. m represents 0 or 1, and the two ms may be the same or different. n represents an integer from 0 to 6. R 1 represents a monovalent substituent, and when there are a plurality of Rs 1 , the plurality of Rs 1 may be the same or different. R 2 represents a hydrogen atom or a monovalent substituent, and the two Rs 2 may be the same or different.

[0040] In compound (A-1), the groups represented by two formulas (X) may be bonded to any position of the 1st to 8th positions of the naphthalene ring. The groups represented by formula (X) on the naphthalene ring may be bonded to any two positions of the 1st to 4th positions (5th to 8th positions), for example, or may be bonded to any one position of the 1st to 4th positions (5th to 8th positions) and any one position of the 5th to 8th positions (1st to 4th positions). It is preferable that the groups represented by formula (X) on the naphthalene ring are bonded to any one position of the 1st to 4th positions (5th to 8th positions) and any one position of the 5th to 8th positions (1st to 4th positions).

[0041]

Chemical formula

[0042] In formula (X), L, A 1 , m, and R 2 have the same meanings as described above, and * represents the bonding position.

[0043] When compound (A-1) has one or more monovalent substituents represented by R 1 , the monovalent substituent represented by R 1 may be bonded to any position from the 1st to the 8th positions of the naphthalene ring excluding the bonding position of the group represented by formula (X).

[0044] L represents a single bond or a divalent group, and the two Ls may be the same or different. In compound (A-1), at least one of the two Ls is preferably an alkanediyl group, and more preferably both are alkanediyl groups. In this case, the number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0045] A 1 represents an oxygen atom or a sulfur atom, and the two As 1 may be the same or different. However, at least one of the two As 1 is a sulfur atom. In compound (A-1), the two As 1 are preferably both sulfur atoms. As the number of sulfur atoms as A 1 increases, a cured product showing a higher refractive index can be obtained, and there is a tendency to be more excellent in curability.

[0046] m represents 0 or 1, and the two ms may be the same or different. In compound (A-1), the two ms are preferably both 0.

[0047] n represents an integer from 0 to 6. n is preferably an integer from 0 to 3, more preferably an integer from 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

[0048] R 1 represents a monovalent substituent. When there are a plurality of R 1 's, the plurality of R 1 's may be the same or different. The monovalent substituent represented by R 1 can be exemplified by the same ones as the monovalent substituent represented by R 2 .

[0049] R 2 represents a hydrogen atom or a monovalent substituent. The two R 2 's may be the same or different. In compound (A-1), the two R 2 's are preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group, more preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group, or an ethyl group.

[0050] Examples of the component (A) (compound (A-1)) include compounds represented by formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af). L, A 1 , m, n, R 1 , and R 2 in formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af) have the same meanings as described above.

[0051]

Chemical formula

[0052] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), among the two Ls, at least one is preferably an alkanediyl group, and more preferably both are alkanediyl groups. In this case, the number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0053] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), the two m's are each independently 0 or 1, and are preferably 0. In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), the two m's are preferably both 0.

[0054] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), n is each independently an integer from 0 to 6, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

[0055] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), the two A's 1 are each independently an oxygen atom or a sulfur atom. However, at least one of the two A's 1 is a sulfur atom. A 1 is preferably both sulfur atoms.

[0056] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), the two R's 2 are each independently preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group, more preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group, or an ethyl group. The two R's 2 are preferably the same.

[0057] Specific examples of compound (A-1) are illustrated below, but are not limited thereto.

[0058]

Chemical formula

[0059]

Chemical formula

[0060]

Chemical formula

[0061]

Chemical formula

[0062]

Chemical formula

[0063]

Chemical formula

[0064]

Chemical formula

[0065]

Chemical formula

[0066]

Chemical formula

[0067]

Chemical formula

[0068]

Chem.

[0069]

Chem.

[0070]

Chem.

[0071]

Chem.

[0072]

Chem.

[0073]

Chem.

[0074] (A) component has a molecular weight of preferably 2000 or less, more preferably 1000 or less, still more preferably 750 or less from the viewpoint of synthesis. (A) component has a molecular weight of preferably 50 or more, more preferably 100 or more, still more preferably 150 or more from the viewpoint of volatility.

[0075] (A) component as compound (A-1) can be obtained by synthesizing a compound represented by formula (A-1a) (hereinafter sometimes referred to as "compound (A-1a)") and reacting compound (A-1a) with a sulfurizing agent.

[0076]

Chem.

[0077] In formula (A-1a), L, m, n, R 1 , and R 2 represent the same meaning as in the above (formula (A-1)).

[0078] Compound (A-1a) can be obtained, for example, by a method including a step of reacting a compound represented by formula (A-2) (hereinafter sometimes referred to as "compound (A-2)") with a compound represented by formula (A-3) (hereinafter sometimes referred to as "compound (A-3)").

[0079]

Chemical formula

[0080] In formula (A-2), n and R 1 represent the same meaning as above.

[0081]

Chemical formula

[0082] In formula (A-3), L, m, and R 2 represent the same meaning as above, and X represents a leaving group.

[0083] The reaction between compound (A-2) and compound (A-3) can be carried out, for example, in the presence of a base. Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, sodium hydride, lithium aluminum hydride, sodium borohydride, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, cesium bicarbonate; metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, potassium t-butoxide; organic bases such as ammonia, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylethylamine, triisopropylamine, DBU (diazabicycloundecene), DABCO (1,4-diazabicyclo[2.2.2]octane), pyridine, 2,6-dimethylpyridine, 2,6-di-t-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, tetramethylammonium chloride. The amount of the base used may be, for example, 0.0001 to 10 moles, preferably 0.001 to 5 moles, more preferably 0.01 to 4 moles, still more preferably 0.1 to 3 moles per 1 mole of compound (A-2).

[0084] Also, two or more types of bases may be used in combination. When used in combination, it is preferably a combination of a carbonate such as sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, etc., or a hydrogen carbonate such as sodium hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, cesium hydrogen carbonate, etc., and a metal hydroxide such as sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, etc., or a metal alkoxide such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, potassium t-butoxide, etc., and more preferably a combination of a hydrogen carbonate and a metal hydroxide. When used in combination, two types may be added simultaneously or stepwise.

[0085] In the compound (A-3), examples of the leaving group represented by X include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, trifluoromethylsulfonyl group, perfluoroethylsulfonyl group, perfluoropropylsulfonyl group, perfluorobutylsulfonyl group; arylsulfonyl groups such as phenylsulfonyl group, p-toluenesulfonyl group, p-fluorophenylsulfonyl group, pentafluorophenylsulfonyl group, etc. Specific examples of the compound (A-3) include epihalohydrin compounds (compounds in which L is a methylene group, m is 0, R 2 is a hydrogen atom, and X is a halogen atom). The amount of the compound (A-3) to be used may be, for example, 0.01 to 20 moles, preferably 0.5 to 15 moles, per 1 mole of the compound (A-2). In this step, the reaction may be carried out using two or more types of the compound (A-3).

[0086] The reaction between compound (A-2) and compound (A-3) is preferably carried out in a solvent. Examples of the solvent include, in addition to water, organic solvents such as ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glymes, esters, aliphatic nitriles, sulfoxides, amides, etc. The following solvents are exemplified as the organic solvent.

[0087] Ketones: acetone, methyl ethyl ketone, diethyl ketone, butyl methyl ketone, diisobutyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, 2-heptanone, 2-octanone, cyclopentanone, cyclohexanone, etc. Aromatic hydrocarbons: benzene, toluene, xylene, mesitylene, naphthalene, anisole, nitrobenzene, aniline, tetralin, durene, etc. Halogenated aromatic hydrocarbons: chlorobenzene, dichlorobenzene, chloronaphthalene, etc. Aliphatic hydrocarbons: pentane, hexane, heptane, etc. Halogenated aliphatic hydrocarbons: dichloromethane, chloroform, 1,2-dichloroethane, tetrachloroethane, tetrachloroethylene, etc. Ethers: diethyl ether, diisopropyl ether, methyl t-butyl ether, cyclopentyl methyl ether, diphenyl ether, dimethoxyethane, dioxane, etc. Alcohols: methanol, ethanol, propanol, isopropanol, butanol, t-butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, hexafluoroisopropanol, etc. Glymes: methyl diglyme, ethyl diglyme, triglyme, diethylene glycol butyl methyl ether, etc. Esters: methyl acetate, ethyl acetate, propyl acetate, butyl acetate, etc. Aliphatic nitriles: acetonitrile, etc. Sulfoxides: dimethyl sulfoxide, sulfolane, etc. Amides: N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0088] The reaction temperature between compound (A-2) and compound (A-3) may be, for example, -80 to 200 °C, preferably -40 to 150 °C, more preferably -20 to 120 °C, and even more preferably -5 to 100 °C.

[0089] In this way, compound (A-1a) can be obtained. When using the compound (A-1a) obtained in the synthesis of compound (A-1), the compound (A-1a) may be used after isolation, or may be used as it is without isolation.

[0090] Compound (A-1) can be obtained, for example, by a method including a step of reacting compound (A-1a) with a sulfurizing agent.

[0091] The reaction between compound (A-1a) and the sulfurizing agent is a reaction in which the oxygen atom of the epoxy ring or oxetanyl ring possessed by compound (A-1a) is substituted with a sulfur atom using the sulfurizing agent to form a thiirane ring (episulfide ring) or a thietane ring. Examples of the sulfurizing agent include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylene thiourea, phenylthiourea, diphenylthiourea, tolylthiourea, ditolylthiourea, sodium thiocyanate, potassium thiocyanate, etc. The amount of the sulfurizing agent to be used can be arbitrarily adjusted according to the oxygen atom to be substituted. The amount of the sulfurizing agent to be used is, for example, 0.01 to 20 moles, preferably 0.5 to 10 moles, per 1 mole of compound (A-1a). Also, by adjusting the amount of the sulfurizing agent to be used, the reaction temperature, the reaction time, etc., it is possible to replace both oxygen atoms in compound (A-1a) with sulfur atoms, or to replace one oxygen atom in compound (A-1a) with a sulfur atom.

[0092] The reaction of compound (A-1a) with a sulfurizing agent is preferably carried out in a solvent. Examples of the solvent include the same solvents as those exemplified in the reaction of compound (A-2) and compound (A-3). The reaction of compound (A-1a) with a sulfurizing agent may be, for example, at -80 to 200 °C, preferably -40 to 100 °C, more preferably -20 to 80 °C, and even more preferably -5 to 60 °C.

[0093] A polymerization inhibitor may be added to the reaction system to suppress the polymerization of the produced compound (A-1). Examples of the polymerization inhibitor include acids, acid anhydrides, etc. More specifically, inorganic acidic compounds such as nitric acid, hydrogen chloride (hydrochloric acid), perchloric acid, hypochlorous acid, chlorine dioxide, hydrofluoric acid, sulfuric acid, fuming sulfuric acid, sulfuryl chloride, boric acid, arsenic acid, arsenous acid, pyroarsenic acid, phosphoric acid, phosphorous acid, hypophosphorous acid, phosphoryl chloride, phosphoryl bromide, phosphorus sulfide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, hydrocyanic acid, chromic acid, nitric anhydride, sulfuric anhydride, boron oxide, arsenic pentoxide, phosphorus pentoxide, chromic anhydride, silica, alumina, aluminum chloride, zinc chloride, lithium hydrogen phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, cesium hydrogen phosphate, lithium dihydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, cesium dihydrogen phosphate; organic carboxylic acids such as formic acid, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, caproic acid, caprylic acid, naphthenic acid, methyl mercaptopropionate, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid acetate, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m-toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, benzylic acid, α-naphthalenecarboxylic acid, β-naphthalenecarboxylic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, trifluoroacetic anhydride; Phosphoric acids such as mono-, di- and trimethyl phosphate, mono-, di- and triethyl phosphate, mono-, di- and triisobutyl phosphate, mono-, di- and tributyl phosphate, mono-, di- and trilauryl phosphate, and phosphorous acids in which these phosphate moieties have become phosphites; Organic phosphorus compounds such as dialkyldithiophosphoric acids typified by dimethyldithiophosphoric acid; Phenols such as phenol, catechol, t-butylcatechol, 2,6-di-t-butylcresol, 2,6-di-t-butylethylphenol, resorcinol, hydroquinone, phloroglucinol, pyrogallol, cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetamide, methyl hydroxyphenylacetate, ethyl hydroxyphenylacetate, hydroxyphenethyl alcohol, hydroxyphenethylamine, hydroxybenzaldehyde, phenylphenol, bisphenol-A, 2,2'-methylene-bis(4-methyl-6-t-butylphenol), bisphenol-F, bisphenol-S, α-naphthol, β-naphthol, aminophenol, chlorophenol, 2,4,6-trichlorophenol; Sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, butanesulfonic acid, dodecanesulfonic acid, benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, ethylbenzenesulfonic acid, butylbenzenesulfonic acid, dodecylbenzenesulfonic acid, p-phenolsulfonic acid, o-cresolsulfonic acid, methanylic acid, sulfanilic acid, 4B-acid, diaminostilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, perylene acid, Laurent acid, phenyl J-acid; etc. are mentioned.

[0094] The amount of the polymerization inhibitor used may be, for example, 0.0001 to 1.0 mol, preferably 0.001 to 0.5 mol, more preferably 0.01 to 0.25 mol, still more preferably 0.05 to 0.15 mol, per 1 mol of the compound (A-1). Among these, the polymerization inhibitor is preferably acetic acid, acetic anhydride, maleic acid, maleic anhydride, phosphoric acid, an alkali metal hydrogen phosphate, or an alkali metal dihydrogen phosphate.

[0095] The stability of the compound (A-1) over time can be improved by washing the product solution after the reaction with an acidic aqueous solution. Specific examples of the acid used in the acidic aqueous solution include the acids exemplified as the polymerization inhibitor above. The acid may be used alone or in combination of two or more. The acidic aqueous solution usually tends to exhibit an effect at pH 6 or lower, but a more effective range is pH 3 or lower. The acid used in the acidic aqueous solution is preferably an aqueous solution of hydrogen chloride (hydrochloric acid), sulfuric acid, phosphoric acid, and / or maleic acid.

[0096] Furthermore, a hydrogen sulfide adsorbent can also be used to improve the stability of the compound (A-1). Examples of the hydrogen sulfide adsorbent include iron(III) hydroxide, zinc oxide, KNK-301 (a zinc oxide-based adsorbent, manufactured by Kureha Corporation), Nionon 202A (an iron oxide-based adsorbent, manufactured by Masashi Ibuki Co., Ltd.), Limonic (an iron hydroxide-based, manufactured by Nippon Limonite Co., Ltd.), and the like. The hydrogen sulfide adsorbent may be added during the reaction or used by adding it during the purification after the reaction.

[0097] The content of the component (A) may be, for example, 30 to 99% by mass based on the total amount of the solid content of the composition because the effects of the present invention can be easily obtained sufficiently. The content of the component (A) is preferably 40% by mass or more, more preferably 50% by mass or more, still more preferably 60% by mass or more, preferably 97% by mass or less, more preferably 95% by mass or less, still more preferably 92% by mass or less, based on the total amount of the solid content of the composition.

[0098] The total amount of the solid content of the composition means the total of the components contained in the composition excluding the solvent. The content of each component in the solid content of the composition can be measured by known analytical means such as liquid chromatography and gas chromatography. The content of each component in the solid content of the composition may be calculated from the formulation at the time of preparing the composition.

[0099] (B) component: Compound (B) The composition of this embodiment contains the (B) component. The (B) component is at least one selected from the group consisting of a compound having a skeleton represented by the formula (I) (hereinafter sometimes referred to as "Compound (I)") and its salt, and a compound having a skeleton represented by the formula (II) (hereinafter sometimes referred to as "Compound (II)") and its salt. The (B) component can be a component that acts as a base catalyst (anionic polymerization catalyst). That is, the (B) component can be a component that releases a base that initiates anionic polymerization by at least one of active energy ray irradiation and heat. By the composition containing the (A) component and the (B) component, it has excellent storage stability and can provide a cured product having excellent curability and heat resistance. From the viewpoints of curability and heat resistance, the (B) component is preferably Compound (I) and its salt.

[0100] Compound (I) can also be referred to as, for example, "a compound having a guanidine skeleton (guanidine compound)". Compound (II) can also be referred to as, for example, "a compound having a phosphazene skeleton (phosphazene compound)". By forming these compounds into salts, their storage stability can be enhanced. The (B) component is preferably a salt of these compounds. From the viewpoints of curability and heat resistance, the (B) component is more preferably a salt of Compound (I), and still more preferably an organic carboxylate salt of Compound (I).

[0101] [Chemical formula]

[0102] In formula (I), R 1Arepresents a hydrogen atom or a hydrocarbon group which may have a substituent.

[0103] Examples of the hydrocarbon group which may have a substituent include, for example, a monovalent aliphatic chain hydrocarbon group which may have a substituent, a monovalent alicyclic hydrocarbon group which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent group composed of a combination of these (for example, an aralkyl group), etc. The methylene group (-CH2-) contained in the monovalent substituent may be substituted with -O-, -S-, -NR B -(R B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).), -CO-, or -SO2-. Specific examples of these hydrocarbon groups are the same as those exemplified by the monovalent substituents represented by the above R 2 can be exemplified.

[0104] R 1A is preferably a hydrocarbon group which may have a substituent from the viewpoints of curability and heat resistance.

[0105] Compound (I) is preferably a compound represented by formula (I-1) (hereinafter, may be referred to as "compound (I-1)"), more preferably a compound represented by formula (I-2) (hereinafter, may be referred to as "compound (I-2)").

[0106]

Chemical formula

[0107] In formula (I-1), R 1A has the same meaning as described above. R 1B , R 1C , R 1D , and R 1E each independently represent a hydrogen atom, a hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent. R 1A and R 1B , R1B and R 1C , R 1C and R 1D , R 1D and R 1E , and, R 1E and R 1A and R may each independently form, together with an adjacent nitrogen atom to which they are attached, an aliphatic heterocyclic ring which may have a substituent.

[0108] R 1B , R 1C , R 1D , and R 1E The hydrocarbon group which may have a substituent in R, R, R, and R may be the same as the hydrocarbon group which may have a substituent in R. 1A The heterocyclic group which may have a substituent in R, R, R, and R may be the same as the heterocyclic group which may have a substituent in the monovalent substituent represented by R above. 1B , R 1C , R 1D , and R 1E The heterocyclic group which may have a substituent in R, R, R, and R may be the same as the heterocyclic group which may have a substituent in the monovalent substituent represented by R above. 2

[0109] The number of carbon atoms of the aliphatic heterocyclic ring is preferably 3 to 6, more preferably 3 to 4. Examples of the substituent which the aliphatic heterocyclic ring may have include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group and the like.

[0110]

Chemical formula

[0111] In formula (I-2), R 1A has the same meaning as described above. Ring X 1A and ring X 1B each independently represent an aliphatic heterocyclic ring which may have a substituent.

[0112] Preferred embodiments of the aliphatic heterocyclic ring which may have a substituent in compound (I-2) may be the same as the preferred embodiments of the aliphatic heterocyclic ring which may have a substituent in compound (I-1).

[0113] Specific examples of compound (I) are illustrated below, but are not limited thereto.

[0114]

Chemical formula

[0115]

Chemical formula

[0116] From the viewpoint of compatibility, the molecular weight of compound (I) is preferably 1000 or less, more preferably 700 or less, and still more preferably 500 or less. From the viewpoint of volatility, compound (I) is preferably 50 or more, more preferably 70 or more, and still more preferably 100 or more.

[0117] The salt of compound (I) is an ionic compound composed of compound (I) and an acid, and is composed of a cation and an anion. Examples of the anion of compound (I) (the anion constituting the acid) include inorganic anions and organic anions. Examples of the anion include hydroxide ion; halide ions such as chloride ion, bromide ion, and iodide ion; carbonate ion; bicarbonate ion; nitrate ion; sulfate ion; sulfite ion; chromate ion; dichromate ion; phosphate ion; cyanide ion; complex ions such as permanganate ion and hexacyanoferrate (III) ion; and organic carboxylate ions such as formate ion, acetate ion, propionate ion, butyrate ion, and valerate ion.

[0118] The anion of compound (I) is preferably an organic carboxylate ion from the viewpoints of curability, heat resistance, and storage stability. The number of carbon atoms constituting the organic carboxylate ion is preferably 1 to 20, more preferably 1 to 10.

[0119] Compound (I) and its salts are preferably salts of compound (I), more preferably organic carboxylate salts of compound (I), from the viewpoints of reaction control and storage stability.

[0120] Specific examples of the salts of compound (I) are exemplified below, but are not limited thereto.

[0121]

Chemical formula

[0122]

Chemical formula

[0123]

Chemical formula

[0124] For compound (I) and its salts, commercially available products can be used, for example.

[0125]

Chemical formula

[0126] In formula (II), R 2A represents a hydrocarbon group which may have a substituent, or -P(=NR 2x1 )(N(R 2x2 )2)2. R 2x1 and R 2x2 each independently represent a hydrocarbon group which may have a substituent, and a plurality of R 2x2 may be the same or different from each other. Two Rs 2x2 may combine with each other to form, together with the adjacent nitrogen atoms, an aliphatic heterocyclic ring which may have a substituent. Each dashed line represents two single bonds or one double bond.

[0127] R 2A 、R 2x1 、and R 2x2 The hydrocarbon group which may have a substituent in may be the same as the hydrocarbon group which may have a substituent in R 1A .

[0128] Compound (II) is preferably a compound represented by formula (II-1) (hereinafter sometimes referred to as "compound (II-1)"), more preferably a compound represented by formula (II-2) (hereinafter sometimes referred to as "compound (II-2)").

[0129]

Chemical formula

[0130] In formula (II-1), R 2A has the same meaning as described above. Each dashed line represents two single bonds or one double bond. -N…L 2A The group represented by is -N(R 2A1 )2, -[N=P(N(R 2A2 )2)2] n2A -N=P(N(R 2A3 )2)3, or -N=C(N(R 2A4 )2)2. n2A represents any integer from 0 to 3. R 2A1 、R 2A2 、R 2A3 、and R 2A4 each independently represents a hydrocarbon group which may have a substituent, and a plurality of Rs 2A1 、R 2A2 、R 2A3 、and R 2A4may be the same or different from each other. Two Rs 2A1 Two Rs 2A2 Two Rs 2A3 and two Rs 2A4 may each independently combine with each other, together with an adjacent nitrogen atom, or together with an adjacent nitrogen atom and a phosphorus atom adjacent to the nitrogen atom, to form an aliphatic heterocyclic ring which may have a substituent. -N…L 2B The group represented by is -N(R 2B1 )2, -[N=P(N(R 2B2 )2)2] n2B -N=P(N(R 2B3 )2)3, or -N=C(N(R 2B4 )2)2. n2B represents any integer from 0 to 3. R 2B1 R 2B2 R 2B3 and R 2B4 each independently represent a hydrocarbon group which may have a substituent, and a plurality of Rs 2B1 R 2B2 R 2B3 and R 2B4 may be the same or different from each other. Two Rs 2B1 Two Rs 2B2 Two Rs 2B3 and two Rs 2B4 may each independently combine with each other, together with an adjacent nitrogen atom, or together with an adjacent nitrogen atom and a phosphorus atom adjacent to the nitrogen atom, to form an aliphatic heterocyclic ring which may have a substituent. -N…L 2C The group represented by is -N(R 2C1 )2, -[N=P(N(R 2C2 )2)2] n2C -N=P(N(R 2C3 )2)3, or -N=C(N(R 2C4 )2)2. n2C represents any integer from 0 to 3. R 2C1 R 2C2 R2C3 and R 2C4 each independently represents a hydrocarbon group which may have a substituent, and a plurality of R 2C1 s, R 2C2 s, R 2C3 and R 2C4 may be the same or different from each other. Two R 2C1 s, two R 2C2 s, two R 2C3 s, and two R 2C4 s may each independently combine with each other to form an aliphatic heterocyclic ring which may have a substituent together with the adjacent nitrogen atom, or together with the adjacent nitrogen atom and the phosphorus atom adjacent to the nitrogen atom. -N…L 2A When the group represented by is -N(R 2A1 )2 and the group represented by -N…L 2B is -N(R 2B1 )2, R 2A1 and R 2B1 may combine with each other to form an aliphatic heterocyclic ring which may have a substituent together with the nitrogen atom to which R 2A1 and R 2B1 are respectively bonded and the phosphorus atom adjacent to the nitrogen atom. -N…L 2B When the group represented by is -N(R 2B1 )2 and the group represented by -N…L 2C is -N(R 2C1 )2, R 2B1 and R 2C1 may combine with each other to form an aliphatic heterocyclic ring which may have a substituent together with the nitrogen atom to which R 2B1 and R 2C1 are respectively bonded and the phosphorus atom adjacent to the nitrogen atom.

[0131] R 2A1 s, R 2A2 s, R 2A3 s, R 2A4 s, R 2B1 s, R 2B2 s, R 2B3 s, R 2B4 s, R 2C1 s, R2C2 , R 2C3 , and R 2C4 The hydrocarbon group which may have a substituent in may be the same as the hydrocarbon group which may have a substituent in R 1A .

[0132] A preferred embodiment of the aliphatic heterocyclic ring which may have a substituent in the compound (II-1) may be the same as the preferred embodiment of the aliphatic heterocyclic ring which may have a substituent in the compound (I-1).

[0133]

Chemical formula

[0134] In formula (II-2), R 2A has the same meaning as described above. R 2B , R 2C , R 2D , R 2E , R 2F , and R 2G each independently represent a hydrocarbon group which may have a substituent. R 2B and R 2C , R 2C and R 2D , R 2D and R 2E , R 2E and R 2F , and, R 2F and R 2G each independently may be bonded to each other to form an aliphatic heterocyclic ring which may have a substituent together with an adjacent nitrogen atom, or together with an adjacent nitrogen atom and a phosphorus atom adjacent to the nitrogen atom.

[0135] R 2B , R 2C , R 2D , R 2E , R 2F , and R 2G The hydrocarbon group which may have a substituent in is R 1AIt may be the same as the hydrocarbon group which may have a substituent in [].

[0136] A preferable embodiment of the aliphatic heterocyclic ring which may have a substituent in compound (II-2) may be the same as the preferable embodiment of the aliphatic heterocyclic ring which may have a substituent in compound (I-1).

[0137] Specific examples of compound (II) are illustrated below, but are not limited thereto.

[0138]

Chemical formula

[0139] From the viewpoint of compatibility, the molecular weight of compound (II) is preferably 2000 or less, more preferably 1500 or less, and still more preferably 1200 or less. From the viewpoint of volatility, compound (II) is preferably 50 or more, more preferably 100 or more, and still more preferably 150 or more.

[0140] The salt of compound (II) is an ionic compound composed of compound (II) and an acid, and is composed of a cation and an anion. Examples of the anion of compound (II) (the anion constituting the acid) can be the same as those of the anion of compound (I). From the viewpoints of curability, heat resistance, and storage stability, the anion of compound (II) is preferably an organic carboxylate ion. The number of carbon atoms constituting the organic carboxylate ion is preferably 1 to 20, more preferably 1 to 10.

[0141] Compound (II) and its salt are preferably the salt of compound (II), more preferably the organic carboxylate salt of compound (II), from the viewpoints of controlling reactivity and storage stability.

[0142] Specific examples of the salt of compound (II) are illustrated below, but are not limited thereto.

[0143]

Chemical formula

[0144] As the compound (II) and its salts, for example, commercially available products can be used.

[0145] From the viewpoint of enhancing curability and / or heat resistance, the content of component (B) is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, based on 100 parts by mass of the total amount of component (A). From the viewpoint of improving physical properties such as the mechanical properties of the cured product, it is preferably 10 parts by mass or less, more preferably 8 parts by mass or less.

[0146] (C) component: polymerization inhibitor (C) The composition may contain one or more (C) components. Whether to contain a polymerization inhibitor in the composition is preferably determined in consideration of, for example, the type of component (A). Component (C) is preferably one that is dissolved or dispersed in a solvent. The (C) component contained in the composition may be added during the preparation of the composition, or may be added after the production of component (A). By containing the (C) component in the composition, unintended polymerization of the (A) component is suppressed, so that the storage stability of the composition can be improved.

[0147] Examples of the (C) component include the same ones as the polymerization inhibitor added to the reaction system to suppress the polymerization of the produced compound (A-1). The (C) component is preferably organic carboxylic acids, more preferably organic carboxylic acids having 10 or fewer carbon atoms, and still more preferably formic acid or acetic acid.

[0148] When the composition contains the (C) component, from the viewpoint of improving the storage stability of the composition, the content of the (C) component is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more, particularly preferably 1 part by mass or more, based on 100 parts by mass of the total amount of component (A), and is preferably 100 parts by mass or less, more preferably 50 parts by mass or less, still more preferably 25 parts by mass or less, particularly preferably 10 parts by mass or less.

[0149] Examples of other components included in the composition include resins, curable compounds other than component (A), solvents, additives, and the like. Examples of additives include inorganic particles, fillers, polymerization initiation aids, sensitizers, leveling agents, stabilizers, surfactants, antistatic agents, lubricants, antifouling agents, ultraviolet absorbers, antioxidants, dispersants, and the like.

[0150] (Resin) The composition may contain one or more resins. By containing a resin in the composition, it is possible to impart developability to the cured product of the composition, or to adjust the mechanical properties and / or optical properties of the cured product and the molded article containing the same. Examples of resins include thermoplastic resins and curable resins. The curable resin may be a photocurable resin that cures upon irradiation with active energy rays, or a thermosetting resin that cures upon heating.

[0151] Examples of thermoplastic resins include olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin; (meth)acrylic resins such as poly(meth)acrylate resin; styrene resins such as polystyrene resin, styrene-acrylonitrile resin, and acrylonitrile-butadiene-styrene resin; vinyl resins such as polyvinyl chloride resin, polyvinylidene chloride resin, polyvinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, and ethylene-vinyl alcohol resin; polyester resins such as polyethylene terephthalate resin, polybutylene terephthalate resin, and liquid crystal polyester resin; polyacetal resin; polyamide resin; polycarbonate resin; polyurethane resin; polyphenylene sulfide resin, and the like. One or more of these resins may be used as a polymer blend or polymer alloy.

[0152] Examples of the curable resin include resins having a photopolymerizable group or a thermopolymerizable group. More specifically, for example, (meth)acrylic resins, epoxy resins, melamine resins, unsaturated polyester resins, phenol resins, urea resins, alkyd resins, polyimide resins, and the like can be mentioned.

[0153] Other examples of the resin include alkali-soluble resins. By containing an alkali-soluble resin in the composition, developability can be imparted to the cured product of the composition. The alkali-soluble resin means a resin soluble in an aqueous alkali solution. Specifically, for example, resins having a carboxy group and / or a phenolic hydroxyl group can be mentioned.

[0154] From the viewpoint of enhancing the developability and solvent resistance of the cured product of the composition, the acid value of the alkali-soluble resin is preferably 10 to 170 mgKOH / g, more preferably 20 to 150 mgKOH / g, and still more preferably 30 to 140 mgKOH / g. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the alkali-soluble resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0155] Also, other examples of the resin include high refractive index resins. The high refractive index resin means a resin having a refractive index of 1.60 or more at a wavelength of 550 nm.

[0156] The weight average molecular weight (Mw) in terms of standard polystyrene measured by gel permeation chromatography (GPC) of the resin may be, for example, 500 to 2,000,000, preferably 1,000 to 1,000,000, and more preferably 1,500 to 750,000. The Mw of the resin can be adjusted by appropriately combining reaction conditions such as the selection of raw materials used, the charging method, the reaction temperature, and the time.

[0157] When the composition contains a resin, the content of the resin is preferably 5% by mass or more, more preferably 10% by mass or more, preferably 80% by mass or less, and more preferably 70% by mass or less based on the total amount of the solid content of the composition.

[0158] (Curable compounds other than component (A)) The composition may contain one or more curable compounds other than component (A). By containing a curable compound other than component (A), the viscosity or curability of the composition can be adjusted, and it is possible to adjust the mechanical properties and / or optical properties of the resulting cured product and the molded product containing the same.

[0159] Examples of the curable compound other than component (A) include, for example, an epoxy compound other than component (A), an oxetane compound other than component (A), a hydroxy compound, a vinyl ether compound, an allyl compound, a thiol compound, a polyphenol compound, an iso(thio)cyanate compound, a (meth)acrylate compound, an acid anhydride, and the like. Among these, the curable compound other than component (A) is preferably a (meth)acrylate compound, that is, a compound having at least one (meth)acryloyl group.

[0160] From the viewpoint of curability, the compound having at least one (meth)acryloyl group is preferably a compound having at least one (meth)acryloyl group and no acidic functional group. Here, the acidic functional group means a group capable of releasing a proton (H + ). However, a group having no releasable proton such as a carboxylate group such as -COONa, a sulfonate group such as -SO3Na, a phosphate group such as -PO4Na2, or a boronate group such as -BO2Na2 (the releasable proton is substituted with an alkali metal ion or the like) is not included in the acidic functional group. Further, the compound having at least one (meth)acryloyl group preferably contains a compound having at least one (meth)acryloyl group and a urethane bond in the molecule from the viewpoint of excellent film-forming properties and the ability to improve the viscosity of the composition (thicken the composition), and a cured film with a thick film (for example, 1.0 μm or more) can be obtained by using the composition.

[0161] When the composition contains a curable compound other than the component (A), the content of the curable compound other than the component (A) is preferably 1% by mass or more, more preferably 2% by mass or more, based on the total amount of the solid content of the composition, and preferably 30% by mass or less, more preferably 20% by mass or less.

[0162] (Solvent) The composition may contain one or more solvents. The solvent is preferably one that can dissolve or disperse the component (A), and more preferably one that can further dissolve or disperse other components other than the component (A). Examples of the solvent include, for example, the solvents (organic solvents) exemplified in the reaction of the compound (A-2) and the compound (A-3), ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

[0163] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, 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, cyclohexanol acetate, γ-butyrolactone, and the like.

[0164] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

[0165] Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and the like.

[0166] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, and the like.

[0167] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.

[0168] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene, and the like.

[0169] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

[0170] When the composition contains a solvent, the content of the solvent is preferably 60 parts by mass or more, more preferably 80 parts by mass or more, and preferably 1000 parts by mass or less, more preferably 500 parts by mass or less, based on 100 parts by mass of the total amount of the solid components of the composition. When the composition contains a solvent, the solid content concentration of the composition is preferably 5 to 60% by mass, more preferably 10 to 50% by mass.

[0171] <Cured Product and Molded Product> The cured product of one embodiment is the cured product of the composition. The molded product of one embodiment is obtained by curing the composition and includes the cured product of the composition. Since the composition is excellent in film-forming property, curability, etc., it can be suitably used as a curable material for producing a cured product or a molded product containing the same. The cured product can be obtained by curing the component (A) etc. in the composition by at least one of irradiation with active energy rays and heat. The shape of the molded product containing the cured product is not particularly limited and may include a film (membrane) shape, plate shape, lens shape, powder shape, granular shape, non-spherical particle shape, crushed particle shape, porous shape, massive continuum, fibrous shape, tubular shape, hollow fiber shape, etc., and may be any shape according to the use of the molded product, etc.

[0172] The method for obtaining a molded article from the composition is not particularly limited, and examples include a method of forming a film on a substrate and then performing molding by etching or the like, an injection molding method, a cast polymerization molding method, and the like.

[0173] In the cast polymerization molding method, for example, the composition is injected into a molding mold, defoaming or the like is performed as necessary, then it is cured by heating in an oven or the like, and the obtained molded article is taken out. The taken-out molded article can be further irradiated with active energy rays to perform additional curing.

[0174] When forming a film as a molded article on a substrate, the composition is applied to the substrate, dried as necessary to form a coating film (coating layer), and the coating film (coating layer) is cured to obtain a cured film (cured layer) as the molded article. The molded article may be a patterned cured film (cured layer). The patterned cured film can be obtained by patterning by methods such as photolithography, inkjet method, printing method, etc. The patterning method may be, for example, a photolithography method. The photolithography method is a method of applying the composition to a substrate, drying as necessary to form a coating film (coating layer), exposing the coating film (coating layer) through a photomask, and developing the exposed coating film (coating layer).

[0175] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, soda lime glass with a silica-coated surface, and non-alkali glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; substrates with aluminum, silver, silver / copper / palladium alloy thin films, etc. formed on these substrates. Examples of the method for applying the composition to the substrate include spin coating method, slit coating method, slit and spin coating method, etc.

[0176] The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. For example, from the light with wavelengths in these ranges, light near 436 nm, near 408 nm, or near 365 nm may be selectively extracted by a band-pass filter according to the absorption wavelength of the photoinitiator. Specific examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. After pattern exposure, the coated film (coating layer) after exposure may be heated (pre-development bake) before development.

[0177] As the developer used for development, for example, an aqueous solution, a solvent, etc. containing an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide, etc. can be mentioned. As the solvent, for example, the solvent (organic solvent) exemplified in the reaction of compound (A-2) and compound (A-3) or the above solvent can be used. The developer may contain a surfactant. Examples of the development method include the paddle method, the dipping method, the spray method, etc. Further heating (post-bake) may be performed on the patterned cured film (cured layer) obtained by development.

[0178] Since the cured product or the molded product containing the same is formed from the composition, it can exhibit a high refractive index, and their refractive indices can be controlled to a desired refractive index by adjusting the composition of the composition, etc. The refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm may be 1.65 or more, 1.68 or more, 1.70 or more, 1.72 or more, 1.73 or more, 1.74 or more, 1.75 or more, or 1.76 or more. The refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm may be, for example, 2.00 or less, or 1.90 or less.

[0179] The refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm can be measured, for example, by the following method. First, a coating film is formed on a substrate, the coating film is cured, and a substrate with a cured film formed thereon is obtained. Next, for the substrate with the cured film formed thereon, a visible ultraviolet spectrophotometer (e.g., "V-650" manufactured by JASCO Corporation) equipped with an integrating sphere unit (e.g., "ISV-922" manufactured by JASCO Corporation) is used to measure the transmission spectrum and the reflection spectrum at wavelengths from 300 nm to 800 nm. Then, among the true reflection spectra obtained by subtracting and smoothing the increase and decrease due to the interference of the reflection spectrum from the transmission spectrum and the reflection spectrum, based on the Fresnel formula (e.g., the 5th original edition of Hect Optics I, Maruzen Publishing, 2018, p. 209-226), the refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm is calculated from the value at a wavelength of 550 nm and the refractive index of the substrate. Thereby, the refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm can be determined.

[0180] <Usage> Examples of uses of the cured or molded product include, for example, glass substitutes and their surface coating materials; coating materials for window glass, daylighting glass, and light source protection glass for houses, facilities, transportation equipment, etc.; window films for houses, facilities, transportation equipment, etc.; interior and exterior finishing materials, interior and exterior paints, and paint films formed by such paints for houses, facilities, transportation equipment, etc.; alkyd resin lacquer paints and paint films formed by such paints; acrylic lacquer paints and paint films formed by such paints; members for light sources that emit ultraviolet rays such as fluorescent lamps and mercury lamps; shielding materials for electromagnetic waves generated from precision machinery, electronic and electrical equipment members, various displays, etc.; containers or packaging materials for foods, chemicals, drugs, etc.; bottles, boxes, blisters, cups, for special packaging, compact disc coats, industrial and agricultural sheets or film materials; fading preventives for printed matter, dyed products, dyes and pigments, etc.; protective films for polymer supports (for example, for plastic parts of machinery and automobile parts); printed matter overcoats; inkjet medium coatings; laminated matte finishes; optical light films; safety glass / windshield intermediate layers; electrochromic / photochromic applications; overlaminate films; solar heat control films; cosmetics such as sunscreen creams, shampoos, rinses, hair styling products, etc.; clothing fibers and fibers for sportswear, stockings, hats, etc.; household interior items such as curtains, carpets, wallpapers, etc.; medical instruments such as plastic lenses, contact lenses, artificial eyes, etc.; optical supplies such as optical filters, backlight display films, prisms, lenses (for example, spectacle lenses, camera lenses, and microlenses, pickup lenses, etc. described later), mirrors, photographic materials, etc.; stationery such as mold films, transfer stickers, anti-graffiti films, tapes, inks, etc.; display boards, indicators, etc. and their surface coating materials; substrates used in optical devices, etc.; optical waveguides; holograms; LED encapsulants, etc.

[0181] The formed article is suitably used as a lens which is an optical article used in optical devices. Examples of the optical devices include solid-state imaging devices and display devices. In a solid-state imaging device, a lens for the purpose of improving the light condensing efficiency to each photoelectric conversion element is used. Further, in a display device, a lens for the purpose of improving the light extraction efficiency from pixels is used. The lens may be a microlens. Examples of the display device include a liquid crystal display device and an organic EL display device.

[0182] As the high refractive index material, inorganic compounds such as zirconium oxide and titanium oxide have been conventionally known. However, when producing a formed article containing a high refractive index material made of an inorganic compound, molding may not be easy, such as difficulty in the progress of etching, and also, the high refractive index material may scatter during molding to cause a contamination problem. Such problems can be solved by using the high refractive material of the present embodiment which is an organic compound.

[0183] The cured product of the composition of the present embodiment can be suitably used as a main-chain scission type positive resist. In the formation of a resist pattern using the cured product of the composition of the present embodiment, by irradiation with ionizing radiation etc. (for example, electron beam, KrF laser, ArF laser, EUV laser, etc.), the main chain of the polymer of the component (A) constituting the cured product is cleaved in the irradiated portion of the resist film and the molecular weight is reduced. Therefore, a difference in solubility in the developer occurs between the exposed portion and the unexposed portion, and a resist pattern is formed. The resist pattern using the cured product of the composition of the present embodiment can be applied when forming a resist pattern in the manufacture of printed circuit boards such as build-up substrates; semiconductors; photomasks; molds, etc.

Examples

[0184] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. In the following, unless otherwise specified, "part" means "part by mass".

[0185] [Synthesis Example 1] <Synthesis of Compound (Aa-1)> ·Synthesis of Compound (Aa-1a)

Chem.

[0186] The inside of a four-necked flask equipped with a Dimroth condenser and a thermometer was made into a nitrogen atmosphere, and 30 parts of 1,6-naphthalenedithiol, 165 parts of acetone, 45 parts of pure water, and 139 parts of epichlorohydrin were added to the flask and stirred in an ice bath for 15 minutes. Subsequently, 15 parts of sodium hydroxide, 66 parts of acetone, and 203 parts of pure water were added to another flask and completely dissolved, and then dropped into the above four-necked flask over 1 hour. After dropping, the temperature was raised to 30 °C and stirred at 30 °C for 2 hours. The obtained mixture was purified to obtain 46 parts of the compound represented by the formula (Aa-1a).

[0187] 1 H-NMR analysis and LC-MS measurement were performed to confirm the formation of the compound (Aa-1a). 1 H-NMR (deuterated chloroform) δ: 8.37~8.39 (1H), 7.85 (1H), 7.39~7.70 (4H), 3.08~3.29 (5H), 2.94~2.98 (1H), 2.57~2.81 (3H), 2.39~2.41 (1H) LC-MS: [M+H] + = 305.5

[0188] ·Synthesis of Compound (Aa-1)

Chem.

[0189] The inside of a four-necked flask equipped with a Dimroth condenser and a thermometer was made into a nitrogen atmosphere, and 3 parts of the compound (Aa-1a), 30 parts of methanol, 30 parts of toluene, 0.05 part of acetic anhydride, and 3.8 parts of thiourea were added to the flask and stirred at room temperature for 24 hours. The obtained mixture was purified to obtain 2.5 parts of the compound represented by the formula (Aa-1).

[0190] 1 H-NMR analysis and LC-MS measurement were performed, and it was confirmed that compound (Aa-1) was formed. 1 H-NMR (deuterated chloroform) δ: 8.39 - 8.43 (1H), 7.86 (1H), 7.40 - 7.74 (4H), 3.40 - 3.53 (2H), 3.04 - 3.18 (2H), 2.78 - 2.96 (2H), 2.47 - 2.49 (1H), 2.35 - 2.36 (1H), 2.14 - 2.16 (1H), 1.93 - 1.94 (1H) LC-MS: [M + H] + = 337.5

[0191] [Examples 1 - 12 and Comparative Examples 1 - 4] [Preparation of Composition] The compounding ingredients shown in Table 1 were put into a flask in the addition amounts (unit: part) shown in Table 1, and the compositions of Examples 1 - 12 and Comparative Examples 1 - 4 in liquid form were prepared by stirring. The compositions of Examples 1 - 12 and Comparative Examples 1 - 4 were visually observed to be transparent, and it was confirmed that the compounding ingredients were uniformly dissolved.

[0192] The details of the abbreviations of the compounding ingredients shown in Table 1 are as follows. Component (A) · (A - 1): The compound represented by formula (Aa - 1) synthesized in Synthesis Example 1 Component (B) · (B - 1): The compound represented by formula (I - A) [Chemical formula] · (B - 2): The compound represented by formula (I - B) [Chemical formula] · (B - 3): The compound represented by formula (I - C) [Chemical formula] · (B - 4): The compound represented by formula (I - D) [Chemical formula] · (B-5): A compound represented by formula (I-E) [Chemical formula] · (B-6): A compound represented by formula (I-F) [Chemical formula] · (B-7): A compound represented by formula (I-G) [Chemical formula] · (B-8): A compound represented by formula (II-A) [Chemical formula] · (B-9): A compound represented by formula (II-B) [Chemical formula] · (B-10): A compound represented by formula (II-C) [Chemical formula] Component (b) (base catalyst other than component (B)) · (b-1): A compound represented by formula (b-1) [Chemical formula] · (b-2): A compound represented by formula (b-2) [Chemical formula] · (b-3): A compound represented by formula (b-3) [Chemical formula] ·(b - 4): The compound represented by formula (b - 4)

Chemical formula

[0193] <Evaluation test> (1) Formation of the cured film About 3 mL of each of the compositions of Examples 1 to 12 and Comparative Examples 1 to 4 was dropped onto a non - alkaline glass plate (thickness 0.7 mm, manufactured by Corning, "Eagle XG"), and spin - coated using a spin coater (manufactured by Mikasa Co., Ltd., "MS - B100") under the conditions of 1000 rpm and 20 seconds to form a coating film. The non - alkaline glass plate on which the coating film was formed was heated at 60°C for 2 minutes to remove the solvent. Next, the non - alkaline glass plate on which the coating film was formed was post - baked by heating at 120°C for 10 minutes to obtain a non - alkaline glass on which a cured film was formed. When the film thickness of the cured film on the non - alkaline glass was measured with a stylus profilometer (manufactured by Bruker, "DekTak XT"), the film thickness was 1.5 μm for all of them.

[0194] (2) Curing property (film thickness retention rate) Using the non - alkaline glass plate on which the cured film was formed, prepared in (2) above, the curing property (film thickness retention rate) of the composition was evaluated according to the following evaluation criteria. The curing property was evaluated by observing the change in the appearance of the cured film before and after immersing the non - alkaline glass plate on which the cured film was formed in acetone at 23°C for 10 minutes, and calculating the film thickness retention rate (film thickness retention rate = film thickness of the cured film after immersion / film thickness of the cured film before immersion). The results are shown in Table 1. 5: There was no change in appearance, and the film thickness retention rate was 100% or less and 95% or more. 4: There was no change in appearance, and the film thickness retention rate was less than 95% and 90% or more. 3: There was no change in appearance, and the film thickness retention rate was less than 90% and 80% or more. 2: There was no change in appearance, and the film thickness retention rate was less than 80%. 1: Regardless of the film thickness retention rate, the cured film became cloudy after immersion.

[0195] (3) Heat resistance Using the alkali-free glass plate with the cured film formed in the above (2), the heat resistance of the composition was evaluated according to the following evaluation criteria. The heat resistance was evaluated by calculating the change in transmittance at a wavelength of 450 nm of the cured film before and after heating (transmittance change = transmittance of the cured film before heating - transmittance of the cured film after heating) when the alkali-free glass plate with the cured film formed was left standing on a hot plate heated to 260 °C for 5 minutes. The results are shown in Table 1. 5: The transmittance change was 0% or more and less than 2%. 4: The transmittance change was 2% or more and less than 5%. 3: The transmittance change was 5% or more and less than 10%. 2: The transmittance change was 10% or more and less than 15%. 1: The transmittance change was 15% or more.

[0196] (4) Storage stability The compositions of Examples 1 to 12 and Comparative Examples 1 to 4 were stored in brown bottles respectively, and the storage stability of the compositions at room temperature (23 °C) was evaluated according to the following evaluation criteria. The results are shown in Table 1. A: No cloudiness occurred in the composition at the time point of 120 days. B: No cloudiness occurred in the composition at the time point of 90 days, but cloudiness occurred in the composition at the time point of 120 days. C: No cloudiness occurred in the composition at the time point of 60 days, but cloudiness occurred in the composition at the time point of 90 days. D: Cloudiness occurred in the composition at the time point of 60 days.

[0197]

Table 1

[0198] As shown in Table 1, the compositions of the examples were superior to those of the comparative examples in terms of curability, heat resistance, and storage stability. From these results, it was confirmed that the composition of the present invention is excellent in storage stability and can provide a cured product excellent in curability and heat resistance.

Claims

1. A compound (A) having at least one thiirane group or thietane group, and at least one compound (B) selected from the group consisting of a compound having a skeleton represented by formula (I) and a salt thereof, and a compound having a skeleton represented by formula (II) and a salt thereof, A composition containing the same. 【Chemical 1】 [In formula (I), R １Ａ represents a hydrogen atom or a hydrocarbon group which may have a substituent. [Chemical 2] [In formula (II), R ２Ａ represents a hydrocarbon group which may have a substituent, or -P(=NR ２ｘ１ )(N(R ２ｘ２ )) ２ ). ２ is represented by. R ２ｘ１ and R ２ｘ２ each independently represents a hydrocarbon group which may have a substituent, and a plurality of R ２ｘ２ may be the same or different from each other. Each broken line represents two single bonds or one double bond.]

2. The composition according to claim 1, wherein the compound (B) is at least one selected from the group consisting of an organic carboxylate of a compound having a skeleton represented by formula (I) and an organic carboxylate of a compound having a skeleton represented by formula (II).

3. The composition according to claim 1, wherein the compound having a skeleton represented by formula (I) is a compound represented by formula (I-2). 【Chemical Formula 3】 [In formula (I-2), R １Ａ is synonymous with the above. Ring X １Ａ and Ring X １Ｂ each independently represents an aliphatic heterocyclic ring which may have a substituent.]

4. The composition according to claim 1, further containing a polymerization inhibitor (C).

5. The composition according to claim 1, wherein the compound (A) is a compound represented by formula (A-1). 【Chemical 4】 [In formula (A-1), L represents a single bond or a divalent group, and the two Ls may be the same or different. A １ represents an oxygen atom or a sulfur atom, and the two A's １ may be the same or different. However, at least one of the two A's １ is a sulfur atom. m represents 0 or 1, and the two m's may be the same or different. n represents an integer from 0 to 6. R １ represents a monovalent substituent, and when there are a plurality of R １ , the plurality of R １ may be the same or different. R ２ represents a hydrogen atom or a monovalent substituent, and the two Rs ２ may be the same or different.

6. A molded article obtained by curing the composition according to any one of claims 1 to 5.

7. A cured product of the composition according to any one of claims 1 to 5.

8. A display device including the cured product according to claim 7.

9. A solid-state imaging device including the cured product according to claim 7.

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