Compound, colorant, composition, optical filter, spectacle lens, contact lens, and method for producing compound

Abstract

Provided are a compound represented by general formula (1), a colorant, a composition containing the compound, an optical filter, a spectacle lens, a contact lens, and a method for producing the compound.　(1): M1-L1-P1 In general formula (1), M1 represents a group formed by removing any one hydrogen atom from a merocyanine compound having a specific structure, L1 represents a single bond or a divalent linking group, and P1 represents a specific polymerizable group.

Description

Compound, dye, composition, optical filter, eyeglass lens, contact lens, and method for producing compound

[0001] The present disclosure relates to compounds, dyes, compositions, optical filters, eyeglass lenses, contact lenses, and methods for making the compounds.

[0002] Dyes with a small half-width that selectively absorb light having a wavelength of 530 nm to 580 nm are useful for improving the optical properties of various optical components, such as displays, optical filters, eyeglass lenses, and contact lenses. Dyes having a merocyanine skeleton are known as dyes that selectively absorb light having a wavelength of 530 nm to 580 nm. For example, merocyanine compounds that exhibit non-resonant two-photon absorption are known (see Patent Document 1). Furthermore, merocyanine compounds having an allyl group are known as sensitizing dyes for silver halide photosensitive materials (see Patent Document 2).

[0003] Japanese Unexamined Patent Publication No. 2004-279795 Japanese Unexamined Patent Publication No. 5-27356

[0004] For example, when a merocyanine compound is applied to optical applications such as optical filters, eyeglass lenses, and contact lenses, a composition obtained by mixing the merocyanine compound with a resin, a monomer, etc. may be irradiated with active energy rays such as ultraviolet light. However, according to studies by the present inventors, it has been found that the absorbance of the merocyanine compounds described in Patent Documents 1 and 2 after irradiation with active energy rays (after exposure) is significantly reduced compared to the absorbance before irradiation with active energy rays (before exposure) (i.e., the rate of decrease in absorbance after exposure is large).

[0005] An object of one embodiment of the present disclosure is to provide a novel compound or a method for producing the novel compound.An object of another embodiment of the present disclosure is to provide a dye having a small rate of decrease in absorbance after exposure, a composition containing the novel compound, an optical filter, a spectacle lens, or a contact lens containing the novel compound.

[0006] The means for solving the above problems include the following aspects.

[0007] <1> A compound represented by the following general formula (1): M １ -L １ -P １ (1) In general formula (1), M １ represents a group obtained by removing any one hydrogen atom from a compound represented by the following general formula (2): １ represents a single bond or a divalent linking group. １ represents a group represented by any one of the following formulas (P-1) to (P-10).

[0008]

[0009] In general formula (2), X １ is an oxygen atom, a sulfur atom, CR ｘ１ R ｘ２ or NR ｘ３ Represents R ｘ１ , R ｘ２ and R ｘ３ R each independently represents a hydrogen atom or a substituent. １ represents an alkyl group. １ ~V ４ each independently represents a hydrogen atom or a substituent. １ ~V ４ At least two of the groups may be bonded to each other via a linking group or without a linking group to form a ring. ５ ~V ８ A each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. １ represents an acidic nucleus. １ may be cyclic or open-chain.

[0010]

[0011] In formulas (P-1) to (P-10), * represents L １ <2> The compound according to <1>, wherein the partial structure represented by the following general formula (2-A) in the above general formula (2) is represented by any one of the following general formulas (1-a) to (1-w):

[0012]

[0013]

[0014]

[0015] In the above general formula, * １ is V in general formula (2) ８ represents the bonding position with the carbon atom to which X is bonded. ２ and X ３ each independently represents an oxygen atom or a sulfur atom. １ represents an electron-withdrawing group. １ represents a hydrogen atom, a carbamoyl group, an alkyl group, an aryl group, a cyano group, a carboxy group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a halogen atom, an amino group, an acylamino group, an alkylsulfonyl group, an arylsulfonyl group, or a sulfo group. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ <3> X in the above general formula (2) each independently represents a hydrogen atom or a substituent. １ is CR ｘ１ R ｘ２ and R ｘ１ and R ｘ２ each independently represent an alkyl group. <4> A dye which is a compound according to any one of <1> to <3>. <5> A composition comprising a compound according to any one of <1> to <3> and a resin. <6> A composition comprising a compound according to any one of <1> to <3>, a monomer, and a polymerization initiator. <7> An optical filter comprising a compound according to any one of <1> to <3>. <8> A spectacle lens comprising a compound according to any one of <1> to <3>. <9> A contact lens comprising a compound according to any one of <1> to <3>. <10> A method for producing a compound represented by the following general formula (1) using a compound represented by the following general formula (3): M １ -L １ -P １ (1) In general formula (1), M １ represents a group obtained by removing any one hydrogen atom from a compound represented by the following general formula (2): １ represents a single bond or a divalent linking group.１ represents a group represented by any one of the following formulas (P-1) to (P-10).

[0016]

[0017] In general formula (2), X １ is an oxygen atom, a sulfur atom, CR ｘ１ R ｘ２ or NR ｘ３ Represents R ｘ１ , R ｘ２ and R ｘ３ R each independently represents a hydrogen atom or a substituent. １ represents an alkyl group. １ ~V ４ each independently represents a hydrogen atom or a substituent. １ ~V ４ At least two of the groups may be bonded to each other via a linking group or without a linking group to form a ring. ５ ~V ８ A each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. １ represents an acidic nucleus. １ may be cyclic or open-chain.

[0018]

[0019] In formulas (P-1) to (P-10), * represents L １ represents the bonding position with

[0020]

[0021] In general formula (3), R １０ represents a hydrogen atom or an acetyl group. ６ ~V ８ and A １ are V in general formula (2). ６ ~V ８ and A １ It has the same meaning as:

[0022] According to one embodiment of the present disclosure, there is provided a novel compound or a method for producing the novel compound. According to another embodiment of the present disclosure, there is provided a dye having a small rate of decrease in absorbance after exposure, a composition containing the novel compound, an optical filter, a spectacle lens, or a contact lens each containing the novel compound.

[0023] The contents of the present disclosure are described in detail below. These descriptions and examples are intended to illustrate embodiments of the present disclosure and do not limit the scope of the embodiments. In the present disclosure, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in the present disclosure, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit value of that numerical range may be replaced with the value shown in the examples. In the present disclosure, a combination of two or more preferred aspects is a more preferred aspect.

[0024] In the present disclosure, "total solid content" refers to the total mass of components excluding the solvent from the entire composition. Furthermore, as described above, "solid content" refers to components excluding the solvent, and may be, for example, a solid or liquid at 25°C. In the notation of groups (atomic groups) in the present disclosure, notations that do not specify whether they are substituted or unsubstituted include both unsubstituted and substituted groups. For example, the term "alkyl group" includes not only alkyl groups without substituents (unsubstituted alkyl groups) but also alkyl groups with substituents (substituted alkyl groups). The type, position, and number of substituents are not particularly limited. The number of substituents introduced may be, for example, one, two, three, or more. Examples of substituents include monovalent non-metallic atomic groups excluding hydrogen atoms, which can be selected, for example, from the following substituent group Y:

[0025] (Substituent Group Y) Substituent Group Y includes halogen atoms (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom); mercapto group; cyano group; carboxy group; phosphate group; sulfo group; hydroxy group; carbamoyl groups having 1 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and more preferably 2 to 5 carbon atoms (e.g., hydroxycarbamoyl group, methylcarbamoyl group, ethylcarbamoyl group, morpholinocarbamoyl group); sulfamoyl groups having 0 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and more preferably 2 to 5 carbon atoms (e.g., methylsulfamoyl group, ethylsulfamoyl group, group, piperidinosulfamoyl group); a nitro group; an alkyl group having 1 to 30 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methyl group, ethyl group, propyl group, butyl group, t-butyl group, i-butyl group, s-butyl group, pentyl group, t-pentyl group, hexyl group, heptyl group, octyl group, hydroxymethyl group, trifluoromethyl group, benzyl group); a cycloalkyl group having 3 to 30 carbon atoms, preferably 4 to 12 carbon atoms, and more preferably 5 to 8 carbon atoms (e.g., cyclohexyl group, 4-methylcyclohexyl group, 4- alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methoxy, ethoxy, 2-methoxyethoxy, 2-phenylethoxy); aryloxy groups having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms (e.g., phenoxy, p-methylphenoxy, p-chlorophenoxy, naphthoxy); aryloxy groups having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (e.g., phenyl, p-methylphenoxy, p-chlorophenoxy, naphthoxy); acyl groups having 2 to 8 carbon atoms (e.g., acetyl, benzoyl, trichloroacetyl); acyloxy groups having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (e.g., acetyloxy, benzoyloxy); acylamino groups having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (e.g., acetylamino); sulfonyl groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methanesulfonyl, ethanesulfonyl, benzenesulfonyl);Sulfinyl groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methanesulfinyl, ethanesulfinyl, and benzenesulfinyl groups); sulfonylamino groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methanesulfonylamino, ethanesulfonylamino, and benzenesulfonylamino groups); amino groups having 0 to 20 carbon atoms, preferably 0 to 12 carbon atoms, and more preferably 0 to 8 carbon atoms (e.g., unsubstituted amino groups, methylamino groups, dimethylamino groups, and benzylamino groups); group, anilino group, diphenylamino group); ammonium groups having 0 to 15 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms (e.g., trimethylammonium group, triethylammonium group); hydrazino groups having 0 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms (e.g., trimethylhydrazino group); ureido groups having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms (e.g., ureido group, N,N-dimethylureido group); 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 carbon atom imido groups having 1 to 6 carbon atoms (for example, succinimido groups); alkylthio groups having 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 8 carbon atoms (for example, methylthio groups, ethylthio groups, and propylthio groups); arylthio groups having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms (for example, phenylthio, p-methylphenylthio, p-chlorophenylthio, 2-pyridylthio, and naphthylthio); alkoxycarbonyl groups having 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (for example, methoxycarbonyl groups). , ethoxycarbonyl group, 2-benzyloxycarbonyl group); aryloxycarbonyl groups having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms (for example, phenoxycarbonyl group); aryl groups having 6 to 20 carbon atoms, preferably 6 to 15 carbon atoms, and more preferably 6 to 10 carbon atoms (for example, phenyl, naphthyl, p-carboxyphenyl, p-nitrophenyl, 3,5-dichlorophenyl, p-cyanophenyl, m-fluorophenyl, p-tolyl, p-cyclohexylphenyl, p-(4-pentylcyclohexyl)phenyl);The group consists of substituted or unsubstituted heterocyclic groups having 1 to 20 carbon atoms, preferably 2 to 10 carbon atoms, and more preferably 4 to 6 carbon atoms (e.g., pyridyl, 5-methylpyridyl, thienyl, furyl, morpholino, and tetrahydrofurfuryl groups); alkenyl groups having 2 to 20 carbon atoms (e.g., vinyl and allyl groups); and, in cases where these substituents can further have one or more substituents, groups having a substituent selected from the above-mentioned substituents as the further substituent.

[0026] In the present disclosure, "(meth)acrylate" refers to either or both of acrylate and methacrylate, "(meth)acrylic" refers to either or both of acrylic and methacrylic, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl.

[0027] In this specification, the weight average molecular weight and number average molecular weight of a resin are defined as polystyrene equivalent values ​​measured by gel permeation chromatography (GPC). In this disclosure, when the content of "structural units" in a resin is defined by a molar ratio, "structural units" are synonymous with "monomer units." However, in this disclosure, "monomer units" may be modified after polymerization by a polymer reaction or the like. "Room temperature" refers to an ambient temperature that is not specifically temperature-controlled, and in this disclosure, refers to "25°C" unless otherwise specified.

[0028] <Compound> The compound of the present disclosure is a novel compound represented by the following general formula (1) (hereinafter also referred to as "compound of the present disclosure"). １ -L １ -P １ (1) In general formula (1), M １ represents a group obtained by removing any one hydrogen atom from a compound represented by the following general formula (2): １ represents a single bond or a divalent linking group. １ represents a group represented by any one of the following formulas (P-1) to (P-10).

[0029]

[0030] In general formula (2), X １ is an oxygen atom, a sulfur atom, CR ｘ１ R ｘ２ or NR ｘ３ Represents R ｘ１ , R ｘ２ and R ｘ３ R each independently represents a hydrogen atom or a substituent. １ represents an alkyl group. １ ~V ４ each independently represents a hydrogen atom or a substituent. １ ~V ４ At least two of the groups may be bonded to each other via a linking group or without a linking group to form a ring. ５ ~V ８ A each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. １ represents an acidic nucleus. １ may be cyclic or open-chain.

[0031]

[0032] In formulas (P-1) to (P-10), * represents L １ represents the bonding position with

[0033] L in general formula (1) １ represents a single bond or a divalent linking group. Examples of the divalent linking group include an alkylene group (for example, an alkylene group having 1 to 10 carbon atoms, such as a methylene group or an ethylene group), a carbonyl group, an oxycarbonyl group (wherein the carbonyl group is M １ carbonyloxy group (carbonyl group bonds to P １ and bonded to), an ether group, an arylene group (for example, an arylene group having 6 to 20 carbon atoms such as a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, or a 1,4-naphthylene group), a heteroarylene group (for example, a heteroarylene group having 1 to 15 carbon atoms and containing at least one of a sulfur atom, a nitrogen atom, and an oxygen atom such as a 2,5-thienylene group), -NR Ｌ１ -, and divalent linking groups formed by combining two or more of these. Ｌ１ represents a hydrogen atom or a substituent (for example, an alkyl group having 1 to 10 carbon atoms, such as a methyl group or an ethyl group).１ is an alkylene group, a carbonyl group, an ether group, -NR Ｌ１ -, a divalent linking group formed by combining two or more of these, or a single bond is preferred, and an alkylene group or a single bond is more preferred.

[0034] P in general formula (1) １ represents a group represented by any one of the above formulas (P-1) to (P-10), preferably a group represented by any one of the above formulas (P-1) to (P-5), and more preferably a group represented by any one of the above formulas (P-1) to (P-3).

[0035] M in general formula (1) １ represents a group obtained by removing one arbitrary hydrogen atom from the merocyanine compound represented by the general formula (2). That is, one arbitrary hydrogen atom contained in the merocyanine compound represented by the general formula (2) is substituted with "-L" in the general formula (1). １ -P １ " is substituted. R in general formula (2) １ or A １ In the general formula (1), "-L １ -P １ " is preferably substituted.

[0036] The compound represented by formula (2) is preferably a merocyanine compound. １ ~V ４ (i.e., V １ , V ２ , V ３ and V ４ ) each independently represents a hydrogen atom or a substituent. １ ~V ４ may be the same or different. １ ~V ４Examples of the substituent represented by the formula (V) include an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom), an amino group, a hydroxy group, a sulfo group, a carboxy group, an oxycarbonyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonylamino group, a sulfonylamino group, a carbamoyl group, an alkylthio group, an arylthio group, a sulfonyl group, a cyano group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, an azo group, and a silyl group. Each of these substituents may be further substituted with a substituent. １ ~V ４ The substituent represented by the formula (I) is preferably an alkyl group, an aryl group, an alkoxy group, a halogen atom, a hydroxy group, a sulfo group, a carboxy group, an oxycarbonyl group, an alkoxycarbonyl group, or a naphtho group.

[0037] V １ ~V ４ At least two of the groups may be bonded to each other via a linking group or without a linking group to form a ring. １ and V ２ may be linked to form a ring with or without a linking group.

[0038] R in general formula (2) １ represents an alkyl group. １The alkyl group represented by the formula (I) may be linear or branched, and examples thereof include unsubstituted alkyl groups having 18 or less carbon atoms (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, and octadecyl group), and substituted alkyl groups in which unsubstituted alkyl groups having 18 or less carbon atoms are substituted with a substituent (substituted alkyl groups having 18 or less carbon atoms). Examples of the substituents possessed by the substituted alkyl group having 18 or less carbon atoms include a carboxy group, a sulfo group, a cyano group, a halogen atom (e.g., a fluorine atom, a chlorine atom, and a bromine atom), a hydroxy group, an alkoxycarbonyl group having 8 or less carbon atoms (e.g., a methoxycarbonyl group, an ethoxyelbonyl group, a phenoxycarbonyl group, and a benzyloxycarbonyl group), an alkoxy group having 8 or less carbon atoms (e.g., a methoxy group, an ethoxy group, a benzyloxy group, and a phenethyloxy group), a monocyclic aryloxy group having 15 or less carbon atoms (e.g., a phenoxy group and a p-tolyloxy group), an acyloxy group having 8 or less carbon atoms (e.g., an acetyloxy group, a propionyloxy group, and a methyloxy group), an aryloxy group having 15 or less carbon atoms (e.g., a phenyloxy group, a methyl ... Examples of the alkyl group include alkyl groups having 18 or less carbon atoms substituted with an acyl group having 8 or less carbon atoms (for example, an acetyl group, a propionyl group, and a benzoyl group), an acyl group having 8 or less carbon atoms (for example, an acetyl group, a propionyl group, and a benzoyl group), a carbamoyl group (for example, a carbamoyl group, an N,N-dimethylcarbamoyl group, a morpholinocarbonyl group, and a piperidinocarbonyl group), a sulfamoyl group (for example, a sulfamoyl group, an N,N-dimethylsulfamoyl group, a morpholinosulfonyl group, and a piperidinosulfonyl group), and an aryl group having 15 or less carbon atoms (for example, a phenyl group, a 4-chlorophenyl group, a 4-methylphenyl group, and an α-naphthyl group).

[0039] R １ The alkyl group represented by the formula (I) is preferably an unsubstituted alkyl group (for example, a methyl group, an ethyl group, and a propyl group), a substituted alkyl group substituted with an alkoxy group (for example, a methoxyethyl group), a substituted alkyl group substituted with an acyloxy group (for example, an acryloyloxyethyl group and a methacryloyloxyethyl group), or a sulfoalkyl group (for example, a 2-sulfoethyl group, a 3-sulfopropyl group, and a 4-sulfobutyl group).

[0040] A preferred embodiment of the compound represented by general formula (1) is a compound represented by general formula (2) １ The alkyl group represented by the general formula (1) is １ -P １ " is a substitution mode.

[0041] V in general formula (2) ５ ~V ８ (i.e., V ５ , V ６ , V ７ and V ８ ) each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. ５ ~V ８ may be the same or different. ５ ~V ８ The alkyl group represented by the formula (V) may be linear or branched, and is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, etc.), or a substituted alkyl group having 1 to 18 carbon atoms (e.g., a benzyl group, an α-naphthylmethyl group, a 2-phenylethyl group, a trifluoromethyl group, etc.). ５ ~V ８ The aryl group represented by the formula (I) is preferably an aryl group having 6 to 15 carbon atoms (for example, a phenyl group, a tolyl group, a 4-bromophenyl group, etc.). ５ ~V ８ The heterocyclic group represented by the formula (I) is preferably a heteroaryl group having 3 to 15 carbon atoms (for example, 2-thienyl). ５ ~V ８ The substituent represented by the formula (I) is preferably an alkyl group or an aryl group.

[0042] X in general formula (2) １ is an oxygen atom, a sulfur atom, CR ｘ１ R ｘ２ or NR ｘ３ Represents R ｘ１ , R ｘ２ and R ｘ３ R each independently represents a hydrogen atom or a substituent. ｘ１ and R ｘ２ may be the same or different. ｘ１ , R ｘ２ and Rｘ３ The substituent represented by R is preferably an alkyl group or an aryl group, and more preferably an alkyl group. ｘ１ , R ｘ２ and R ｘ３ The alkyl group represented by R may be linear or branched, and is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, etc.) or a substituted alkyl group having 1 to 18 carbon atoms (e.g., a benzyl group, an α-naphthylmethyl group, a 2-phenylethyl group, a trifluoromethyl group, etc.). ｘ１ , R ｘ２ and R ｘ３ The aryl group represented by the formula (I) is preferably an aryl group having 6 to 15 carbon atoms (for example, a phenyl group, a p-tolyl group, a 4-bromophenyl group, etc.).

[0043] X １ is CR ｘ１ R ｘ２ or NR ｘ３ It is preferred that X represents １ is CR ｘ１ R ｘ２ and R ｘ１ and R ｘ２ More preferably, each independently represents an alkyl group.

[0044] A in general formula (2) １ represents an acidic nucleus. １may be cyclic or open-chain. The acidic nucleus referred to here is defined, for example, by James, ed., "The Theory of the Photographic Process," 4th ed., Macmillan Publishing, 1977, p. 198. Specific examples include those described in U.S. Pat. Nos. 3,567,719, 3,575,869, 3,804,634, 3,837,862, 4,002,480, 4,925,777, and JP-A-3-167546. The acidic nucleus preferably contains a five- or six-membered nitrogen-containing heterocycle consisting of carbon, nitrogen, and chalcogen (typically oxygen, sulfur, selenium, and tellurium) atoms, and specific examples include the following nuclei: 2-pyrazolin-5-one, pyrazolidine-3,5-dione, imidazolin-5-one, hydantoin, 2 or 4-thiohydantoin, 2-iminooxazolidin-4-one, 2-oxazolin-5-one, 2-thiooxazolin-2,4-dione, isoxazolin-5-one, 2-thiazolin-4-one, thiazolidin-4-one, thiazolidine-2,4-dione, rhodanine, thiazolidine-2,4-dithione, isorhodanine, indan-1,3-dione, thiophen-3-one, thiophen-3-one-1,1-dioxide, indolin-2-one, indolin-3-one, 2-oxoindazolinium, 3-oxoindazolinium, 5,7-dioxo-6,7-dihydrothio Azolo[3,2-a]pyrimidine, cyclohexane-1,3-dione, cyclopentane-1,3-dione, 3,4-dihydroisoquinolin-4-one, 1,3-dioxane-4,6-dione, barbituric acid, 2-thiobarbituric acid, chroman-2,4-dione, indazoline-2-one, pyrido[1,2-a]pyrimidine-1,3-dione, pyrazolo[1,5-b]quinazolone, pyrazolo[1,5-a]benzimidazole, pyrazolopyridone, 1,2,3,4-tetrahydroquinoline-2,4-dione, 3-oxo-2,3-dihydrobenzo[d]thiophene-1,1-dioxide, 3-dicyanomethine-2,3-dihydrobenzo[d]thiophene-1,1-dioxide nucleus.The acidic nucleus is preferably hydantoin, 2- or 4-thiohydantoin, 2-oxazolin-5-one, 2-thiooxazoline-2,4-dione, thiazolidine-2,4-dione, rhodanine, thiazolidine-2,4-dithione, barbituric acid, 2-thiobarbituric acid, cyclohexane-1,3-dione, or cyclopentane-1,3-dione, more preferably hydantoin, 2- or 4-thiohydantoin, 2-oxazolin-5-one, rhodanine, barbituric acid, 2-thiobarbituric acid, cyclohexane-1,3-dione, or cyclopentane-1,3-dione, even more preferably cyclohexane-1,3-dione, cyclopentane-1,3-dione, 2- or 4-thiohydantoin, 2-oxazolin-5-one, or rhodanine, and particularly preferably cyclohexane-1,3-dione.

[0045] The partial structure represented by the following general formula (2-A) in general formula (2) is preferably represented by any one of the following general formulas (1-a) to (1-w), more preferably represented by the following general formula (1-c), (1-i) or (1-p), and even more preferably represented by the following general formula (1-c) or (1-p).

[0046]

[0047]

[0048]

[0049] In the above general formula, * １ is V in general formula (2) ８ represents the bonding position with the carbon atom to which X is bonded. ２ and X ３ each independently represents an oxygen atom or a sulfur atom. １ represents an electron-withdrawing group. １ represents a hydrogen atom, a carbamoyl group, an alkyl group, an aryl group, a cyano group, a carboxy group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a halogen atom, an amino group, an acylamino group, an alkylsulfonyl group, an arylsulfonyl group, or a sulfo group. Ａ１ , R Ａ２ , RＡ３ , R Ａ４ , R Ａ５ and R Ａ６ each independently represents a hydrogen atom or a substituent.

[0050] Y １ Preferred electron-withdrawing groups represented by the formula (I) include a cyano group, a nitro group, an acyl group, a carboxy group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, and an arylsulfonyl group.

[0051] Z １ The alkyl group represented by Z may be linear or branched, and is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, etc.) or a substituted alkyl group having 1 to 18 carbon atoms (e.g., a benzyl group, an α-naphthylmethyl group, a 2-phenylethyl group, a trifluoromethyl group, etc.). １ The alkyl group contained in the alkyloxycarbonyl group and alkylsulfonyl group represented by the following formula (I), the alkyl group when the acyl group is an alkylcarbonyl group, and the alkyl group when the acylamino group is an alkylcarbonylamino group are also the same as those described above in Z １ The alkyl group is the same as the alkyl group represented by the formula: １ The aryl group represented by the formula (I) is preferably an aryl group having 6 to 15 carbon atoms (for example, a phenyl group, a tolyl group, a 4-bromophenyl group, etc.). １ The aryl group contained in the aryloxycarbonyl group and arylsulfonyl group represented by the following formula (I), the aryl group when the acyl group is an arylcarbonyl group, and the aryl group when the acylamino group is an arylcarbonylamino group are also the same as those described above in Z １ The same applies to the aryl group represented by the formula: １ The halogen atom represented by the formula (I) is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0052] R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ may be the same or different.Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ The substituent represented by R is preferably an alkyl group or an aryl group, and more preferably an alkyl group. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ The alkyl group and aryl group represented by the formula (I) may have a substituent. Examples of the substituent include a substituent selected from the above-mentioned substituent group Y. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ The alkyl group represented by R may be linear or branched, and is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, etc.) or a substituted alkyl group having 1 to 18 carbon atoms (e.g., a benzyl group, an α-naphthylmethyl group, a 2-phenylethyl group, a trifluoromethyl group, etc.). Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ The aryl group represented by the formula (I) is preferably an unsubstituted aryl group having 6 to 15 carbon atoms (for example, a phenyl group, a naphthyl group, etc.) or a substituted aryl group having 6 to 30 carbon atoms (for example, a tolyl group, a 4-bromophenyl group, a styryl group, etc.).

[0053] A preferred embodiment of the compound represented by formula (1) is a compound represented by formula (2) １ The acidic nucleus represented by the general formula (1) is １ -P １ " is a substitution mode.

[0054] <Dye> The compound represented by general formula (1) is useful as a dye. The dye of the present disclosure, which is a compound represented by general formula (1), preferably has a maximum absorption wavelength in the wavelength range of 530 nm to 580 nm.

[0055] The compounds and dyes of the present disclosure have a small rate of decrease in absorbance after exposure (i.e., a small rate of decrease in absorbance due to irradiation with active energy rays). Furthermore, a preferred embodiment of the compounds and dyes of the present disclosure has high radical resistance and is easily immobilized in a polymer due to the polymerizable group allowing for polymerization. "High radical resistance" means that the optical properties of the compounds and dyes are unlikely to change even in an environment where radicals are generated. High radical resistance typically results in a small rate of decrease in absorbance after exposure and a small change in the maximum absorption wavelength between the initial state (before exposure) and after exposure. While the reason for improved radical resistance is unclear, it is presumed that the presence of a specific polymerizable group represented by any one of formulas (P-1) to (P-10) can suppress radical attack on the methine chain (described in general formula (2)) of the compounds and dyes of the present disclosure during radical polymerization of a monomer. Note that the above-described mechanism of action is presumed and does not limit the effects of the present disclosure.

[0056] Specific examples (exemplary compounds) of the compounds and dyes of the present disclosure are listed below. However, the compounds and dyes of the present disclosure are not limited to the exemplary compounds shown below. In the chemical formulas below, the substituents Me, Et, and Ph represent a methyl group, ethyl group, and phenyl group, respectively. Exemplary compounds S-1 to S-12 are compounds represented by the formula V in the following general formula (K1). ２ , V ３ , V ７ , R １ , R Ａ１ and R Ａ２ are compounds shown in Table 1 below. Exemplary compounds S-13 to S-20 are compounds represented by V in the following general formula (K2). ２ , V ３ , V ７ , R １ , R Ａ１ and R Ａ２ are the compounds shown in Table 2 below. ２ indicates the bonding position with the nitrogen atom.

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] The maximum absorption wavelength and absorbance of each of the above exemplary compounds were measured by the following method, and all of them had a maximum absorption wavelength in the wavelength range of 530 nm to 580 nm and an absorbance of 0.60 or more, making them useful as dyes. １ is CR ｘ１ R ｘ２ and R １ or A １ To "-L １ -P １ " is substituted, and P １ In view of ease of immobilization by radical polymerization, S-1 to S-22, each of which is a group represented by formula (P-1) to (P-3), are preferred. S-1 to S-12 are more preferred because they have a particularly small rate of decrease in absorbance after exposure.

[0063] (Measurement of maximum absorption wavelength and absorbance) For each example compound, 3.0 × 10 －５ The sample solution is diluted with chloroform to a concentration of 1000 mol / L, and the absorbance of the resulting solution is measured in a 1 mm quartz cell using a spectrophotometer (UV-3600 Plus, manufactured by Shimadzu Corporation). The maximum absorption wavelength (λmax) is measured from the absorption spectrum of the sample solution.

[0064] <Method for Producing Compound> There are no particular limitations on the method for producing the compound and dye of the present disclosure. The compounds of the present disclosure can be prepared from compounds described, for example, in "Heterocyclic Compounds - Cyanine Dyes and Related Compounds" by F. M. Harmer, John Wiley & Sons, New York, London, 1964; and "Heterocyclic Compounds - Special Topics in Heterocyclic Chemistry" by D. M. Sturmer. The carbon nanotubes can be synthesized based on the method described in "Rodd's Chemistry of Carbon Compounds," 2nd Ed. vol. IV, part B, 1977, Chapter 15, pp. 369-422, Elsevier Science Publishing Company Inc., New York, London, 1977, or the like.

[0065] The compound of the present disclosure can also be produced by a method using a compound represented by the following general formula (3) (also referred to as the "production method of the present disclosure").

[0066]

[0067] In general formula (3), R １０ represents a hydrogen atom or an acetyl group. ６ ~V ８ and A １ are V in general formula (2). ６ ~V ８ and A １ It has the same meaning as:

[0068] In the production method of the present disclosure, a compound represented by the above general formula (3) is used as a starting material. Specific synthesis methods will be described in detail in the Examples.

[0069] A preferred embodiment of the compound of the present disclosure has good optical properties, and considering the maximum absorption wavelength, absorbance, etc., it can be suitably used in optical products such as optical filters, eyeglass lenses, and contact lenses. A preferred embodiment of the compound of the present disclosure has good radical resistance, and therefore can be suitably used in various applications as a composition containing other components. The compound of the present disclosure or a dye that is a compound of the present disclosure can be suitably used, for example, in a composition containing a resin, a polymerizable composition, etc.

[0070] <Composition: First Aspect> The first aspect of the composition of the present disclosure includes the compound of the present disclosure and a resin as described above. The first aspect of the composition of the present disclosure may contain the compound of the present disclosure as a dye. There are no particular limitations on the resin used in the first aspect of the composition of the present disclosure. Considering the properties of the compound of the present disclosure, for example, resins contained in optical filters are suitable. From the above perspective, the resin is preferably a resin capable of forming a film or light-absorbing layer with excellent transparency and mechanical properties. Examples of such resins include polyesters such as polyethylene terephthalate; cellulose esters such as cellulose diacetate, cellulose triacetate, and cellulose acetate butyrate; polyolefins such as polyethylene and polypropylene; polyvinyl compounds such as polyvinyl chloride, polyvinylidene chloride, vinyl chloride-vinyl acetate copolymer, and polystyrene; acrylic addition polymers such as polymethyl methacrylate; polycarbonates made from polycarbonate esters; and gelatin. Among these, polyesters, cellulose esters, or gelatin are preferred as the resin from the standpoints of cost, film quality, and transparency. Furthermore, when the optical filter is a laminate having a light absorbing layer (for example, a blue light absorbing layer) formed on a substrate from a composition containing a resin and the compound of the present disclosure, it is preferable to use a resin having excellent adhesion to the substrate. Examples of resins having excellent adhesion to the substrate include polymethyl methacrylate, cellulose acetate butyrate, and polycarbonate.

[0071] When the composition of the present disclosure is used for eyeglass lenses described below, there are no particular limitations on the resin as long as it satisfies the physical properties required for eyeglass lenses, such as transparency, refractive index, processability, and hardness after curing. When the composition of the present disclosure is used for eyeglass lenses, the resin may be a thermoplastic resin or a thermosetting resin. Examples of thermoplastic resins that can be used for eyeglass lenses include polycarbonate (PC). Examples of thermosetting resins include urethane resins and episulfide resins. As urethane resins, thiourethane resins are preferred. As resins, thiourethane resins are preferred from the viewpoint of their high refractive index, and polycarbonate resins are preferred from the viewpoint of their good transparency.

[0072] From the viewpoint of film strength and uniformity, the resin that can be contained in the composition of the present disclosure preferably has a weight-average molecular weight in the range of 10,000 to 1,000,000, and more preferably in the range of 20,000 to 500,000. The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin in this disclosure are values ​​measured by gel permeation chromatography (GPC) under the following conditions. [Solvent] Tetrahydrofuran [Apparatus] TOSOH HLC-8220GPC (Tosoh Corporation) [Column] Three TOSOH TSKgel Super HZM-H columns (4.6 mm x 15 cm) were used in conjunction. [Column temperature] 25°C [Sample concentration] 0.1% by mass [Flow rate] 0.35 ml / min [Calibration curve] A calibration curve was used using seven samples of TSK standard polystyrene manufactured by TOSOH, with Mw = 2,800,000 to 1,050.

[0073] The resin suitable for the optical filter includes, for example, resins suitable for eyeglass lenses and contact lenses, which will be described later, and can be selected depending on the purpose.

[0074] The content of the compound of the present disclosure in the first aspect of the composition can be appropriately selected depending on the intended use of the composition. For example, the content of the compound of the present disclosure relative to the total solid content of the composition can be in the range of 0.001% by mass to 50% by mass, preferably in the range of 0.01% by mass to 10% by mass. Furthermore, the content of the resin relative to the total solid content of the composition can be in the range of 1% by mass to 99.99% by mass, preferably in the range of 10% by mass to 99.99% by mass.

[0075] <Composition: Second Aspect> A second aspect of the composition of the present disclosure includes the compound, monomer, and polymerization initiator of the present disclosure described above. The second aspect of the composition of the present disclosure may include the compound of the present disclosure as a dye. A preferred aspect of the compound of the present disclosure has excellent radical resistance. Therefore, even in a polymerizable composition (curable composition) containing a monomer and a polymerization initiator, i.e., the second aspect of the composition of the present disclosure, the compound has the advantage that its stability as a dye is maintained and discoloration of the dye is unlikely to occur.

[0076] As the monomer that can be included in the second aspect of the composition of the present disclosure, a known monomer having a polymerizable group can be selected and used depending on the purpose. The monomer may be a radical polymerizable monomer or a cation polymerizable monomer, but a radical polymerizable monomer is preferred because a preferred aspect of the compound of the present disclosure has radical resistance. Examples of the radical polymerizable monomer include compounds having one or more ethylenically unsaturated bonds in the molecule.

[0077] The molecular weight of the monomer that can be used in the second aspect of the composition of the present disclosure, i.e., the radical polymerizable monomer, is preferably less than 2,000, more preferably 1,500 or less. The lower limit of the molecular weight of the monomer is preferably 100 or more, more preferably 200 or more. The compound having an ethylenically unsaturated group as the polymerizable monomer is preferably a trifunctional to 15-functional (meth)acrylate compound, more preferably a trifunctional to hexafunctional (meth)acrylate compound. Specific examples include the compounds described in paragraph 0128 of WO 2022 / 085485 and the compounds described in JP 2017-194662 A, the contents of which are incorporated herein by reference. More specific examples of the monomer include 2-hydroxyethyl methacrylate, methyl methacrylate, butyl acrylate, 2-hydroxyethyl acrylate, benzyl methacrylate, etc.

[0078] As the compound having an ethylenically unsaturated group, the compounds described in paragraphs 0129 to 0137 of WO 2022 / 085485 can also be used. The compound having an ethylenically unsaturated group may be a compound having an acid group such as a carboxy group, a sulfo group, or a phosphate group, a compound having a caprolactone structure, a compound having an alkyleneoxy group, or a compound having a fluorene skeleton.

[0079] As the compound having an ethylenically unsaturated group, it is also preferable to use U-108A, UA-112P, UA-7100 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), and the like.

[0080] The content of the monomer is preferably 0.1% by mass to 99.99% by mass relative to the total solid content of the composition of the second aspect of the present disclosure. The lower limit is more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit is more preferably 99.90% by mass or less, and even more preferably 99.80% by mass or less. In the second aspect of the composition of the present disclosure, only one type of monomer may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof be in the above range.

[0081] As the polymerization initiator that can be contained in the second aspect of the composition of the present disclosure, a known polymerization initiator can be selected and used depending on the purpose. The polymerization initiator may be a thermal polymerization initiator or a photopolymerization initiator. Since a preferred aspect of the compound of the present disclosure has good radical resistance, the second aspect of the composition of the present disclosure can be a polymerizable composition that contains a radical polymerization initiator as the polymerization initiator.

[0082] Radical polymerization initiators that can be used in the second aspect of the composition of the present disclosure include oxime compounds, α-aminoacetophenone compounds, α-hydroxyketone compounds, acylphosphine compounds, and organic peroxides. Among these, oxime compounds are preferred. By using the radical polymerization initiator represented by Formula 1 above in combination with another radical polymerization initiator, a more balanced pattern with good rectangularity can be obtained.

[0083] Examples of oxime compounds include the compounds described in paragraph 0142 of WO 2022 / 085485, the polymers described in JP 2020-172619 A, the compounds represented by formula 1 described in WO 2020 / 152120, and the oxime ester compounds described in WO 2021 / 023144. Specific examples of oxime compounds and commercially available products include the compounds described in paragraph 0142 of WO 2022 / 085485. Commercially available products include TR-PBG-327 (manufactured by Tronley). It is also preferable to use a compound that is not colorable or that is highly transparent and resistant to discoloration as the oxime compound. Commercially available products include ADEKA ARCLES NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA Corporation). Other radical polymerization initiators include fluorenyl amino ketone photoinitiators described in JP-A-2020-507664, photopolymerization initiators represented by the general formula (1) of JP-A-2021-173858, photopolymerization initiators described in paragraphs 0022 to 0024 of JP-A-2021-173858, photopolymerization initiators represented by the general formula (1) of JP-A-2021-170089, photopolymerization initiators described in paragraphs 0117 to 0120 of JP-A-2021-170089, and JP-A-2021 -181406 compounds described in JP-A-2022-013379 photopolymerization initiators described in JP-A-2022-015747 compounds represented by formula (1), fluorine-containing fluorene oxime ester photoinitiators described in JP-T-2021-507058, initiators described in Chinese Patent Application Publication No. 110764367, initiators described in JP-T-2022-518535, initiators described in WO 2021 / 175855, etc. can also be used. In addition, as an oxime compound, compounds described in paragraphs 0143 to 0149 of WO 2022 / 085485 can be used.

[0084] Specific examples of the oxime compound include the compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600. When the polymerization initiator contains an acylphosphine oxide compound and a thioxanthone compound, the readability after a transfer test and the readability after a rub test are improved.

[0085] Examples of the acylphosphine oxide compound include monoacylphosphine oxide compounds and bisacylphosphine oxide compounds, with bisacylphosphine oxide compounds being preferred.

[0086] Examples of the monoacylphosphine oxide compound include isobutyryldiphenylphosphine oxide, 2-ethylhexanoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, (2,4,6-trimethylbenzoyl)ethoxyphenylphosphine oxide, o-toluyldiphenylphosphine oxide, p-t-butylbenzoyldiphenylphosphine oxide, 3-pyridylcarbonyldiphenylphosphine oxide, acryloyldiphenylphosphine oxide, benzoyldiphenylphosphine oxide, pivaloylphenylphosphinic acid vinyl ester, acryloyldiphenylphosphine oxide, benzo ... Examples of the diphenylphosphine oxide include dipoylbisdiphenylphosphine oxide, pivaloyldiphenylphosphine oxide, p-toluyldiphenylphosphine oxide, 4-(t-butyl)benzoyldiphenylphosphine oxide, terephthaloylbisdiphenylphosphine oxide, 2-methylbenzoyldiphenylphosphine oxide, versatoyldiphenylphosphine oxide, 2-methyl-2-ethylhexanoyldiphenylphosphine oxide, 1-methyl-cyclohexanoyldiphenylphosphine oxide, pivaloylphenylphosphine acid methyl ester, and pivaloylphenylphosphine acid isopropyl ester.

[0087] Examples of the bisacylphosphine oxide compound include bis(2,6-dichlorobenzoyl)phenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-ethoxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2-naphthylphosphine oxide, and bis(2,6-dichlorobenzoyl). phenyl)-1-naphthylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-chlorophenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,4-dimethoxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)decylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-octylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2, 5-dimethylphenylphosphine oxide, bis(2,6-dichloro-3,4,5-trimethoxybenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichloro-3,4,5-trimethoxybenzoyl)-4-ethoxyphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-4-ethoxyphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2- naphthylphosphine oxide, bis(2-methyl-1-naphthoyl)-4-propylphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2-methoxy-1-naphthoyl)-4-ethoxyphenylphosphine oxide, bis(2-chloro-1-naphthoyl)-2,5-dimethylphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide.

[0088] Of these, the acylphosphine oxide compound is preferably bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (product name "Omnirad 819", manufactured by IGM Resins B.V.), 2,4,6-trimethylbenzoyldiphenylphosphine oxide (product name "Omnirad TPO H", manufactured by IGM Resins B.V.), or (2,4,6-trimethylbenzoyl)ethoxyphenylphosphine oxide (product name "Omnirad TPO-L", manufactured by IGM Resins B.V.).

[0089] Examples of thioxanthone compounds include thioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-dodecylthioxanthone, 2,4-diethylthioxanthone, 2,4-dimethylthioxanthone, 1-methoxycarbonylthioxanthone, 2-ethoxycarbonylthioxanthone, 3-(2-methoxyethoxycarbonyl)thioxanthone, 4-butoxycarbonylthioxanthone, and 1-methyl-2-methyl-2-methylthioxanthone. thioxanthone, 3-butoxycarbonyl-7-methylthioxanthone, 1-cyano-3-chlorothioxanthone, 1-ethoxycarbonyl-3-chlorothioxanthone, 1-ethoxycarbonyl-3-ethoxythioxanthone, 1-ethoxycarbonyl-3-aminothioxanthone, 1-ethoxycarbonyl-3-phenylsulfurylthioxanthone, 3,4-di[2-(2-methoxyethoxy)ethoxycarbonyl]thioxanthone, 1-ethoxycarbonyl-3-phenylsulfurylthioxanthone, thioxanthone, 2-methyl-6-dimethoxymethylthioxanthone, 2-methyl-6-(1,1-dimethoxybenzyl)thioxanthone, 2-morpholinomethylthioxanthone, 2-methyl-6-morpholinomethylthioxanthone, n-allylthioxanthone-3,4-dicarboximide, n-octylthioxanthone-3,4-dicarboximide, N-(1,1,3,3-tetramethylthioxanthone), methylbutyl)thioxanthone-3,4-dicarboximide, 1-phenoxythioxanthone, 6-ethoxycarbonyl-2-methoxythioxanthone, 6-ethoxycarbonyl-2-methylthioxanthone, thioxanthone-2-polyethylene glycol ester, and 2-hydroxy-3-(3,4-dimethyl-9-oxo-9H-thioxanthone-2-yloxy)-N,N,N-trimethyl-1-propanaminium chloride.

[0090] The thioxanthone compound may be a commercially available product, such as the SPEEDCURE series manufactured by Lambson (e.g., SPEEDCURE 7010, SPEEDCURE CPTX, SPEEDCURE ITX, etc.).

[0091] Specific examples of the radical polymerization initiator that can be included in the second aspect of the composition of the present disclosure include phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, Adeka Arcles NCI-730, and the like.

[0092] The second aspect of the composition of the present disclosure may contain only one type of polymerization initiator, or may contain two or more types. From the viewpoint of sensitivity, the content of the polymerization initiator in the second aspect of the composition is preferably 0.01% by mass to 30% by mass, more preferably 0.05% by mass to 25% by mass, even more preferably 0.1% by mass to 20% by mass, and particularly preferably 1% by mass to 15% by mass, relative to the total solid content of the composition.

[0093] By including a monomer and a polymerization initiator in the composition of the present disclosure, a second aspect of the composition of the present disclosure can be a pattern-forming composition that cures only the areas to which energy is applied by localized application of energy such as patterned exposure. Even in such applications, by including a compound of the present disclosure as a dye, fading of the dye is suppressed even if radicals are generated during curing by application of energy, and a cured product with a stable hue can be obtained.

[0094] The content of the compound of the present disclosure in the second aspect of the composition can be appropriately selected depending on the application of the composition. As an example, the content of the compound of the present disclosure relative to the total solid content of the composition can be in the range of 0.001% by mass to 50% by mass, preferably in the range of 0.01% by mass to 10% by mass. The content of the monomer relative to the total solid content of the second aspect of the composition can be in the range of 1% by mass to 99.99% by mass, preferably in the range of 10% by mass to 99.99% by mass. Furthermore, the content of the polymerization initiator relative to the total solid content of the second aspect of the composition can be in the range of 0.0001% by mass to 10% by mass, preferably in the range of 0.001% by mass to 5% by mass, relative to the total mass of the monomer.

[0095] (Other Components) The composition of the present disclosure may contain other known components in addition to the compound, resin, monomer, and polymerization initiator of the present disclosure. Examples of other components include known plasticizers, organic acids, dyes, UV absorbers, antioxidants, and matting agents. For details, please refer to paragraphs

[0062] to

[0097] of JP 2012-155287 A, the contents of which are incorporated herein by reference. Other components also include peel accelerators, organic acids, and polycarboxylic acid derivatives. For details, please refer to paragraphs

[0212] to

[0219] of WO 2015 / 005398, the contents of which are incorporated herein by reference. Furthermore, other components may include radical scavengers, antidegradants, and barbituric acid compounds. When other components are contained, the total content thereof is preferably in the range of, for example, 1% by mass to 30% by mass relative to the total mass of the resin, and is preferably in the range of 0.1% by mass to 10% by mass relative to the total mass of the monomer and the polymerization initiator.

[0096] The composition of the present disclosure may contain an organic solvent from the viewpoint of moldability and handling. After molding the composition, the organic solvent may be removed by heating or the like.

[0097] The compounds of the present disclosure have good optical properties and can therefore be suitably used in optical applications such as optical filters, eyeglass lenses, and contact lenses.

[0098] <Optical Filter> The optical filter of the present disclosure includes the compound of the present disclosure described above. The optical filter of the present disclosure may be obtained from a composition containing a resin in addition to the compound of the present disclosure, or may be obtained from a composition containing a monomer and a polymerization initiator in addition to the compound of the present disclosure.

[0099] The optical filter of the present disclosure can be composed of a film formed from a composition containing the compound of the present disclosure and a resin. The optical filter may be composed solely of a film formed from the composition of the present disclosure, or may be a laminate having an optical filter layer formed from a composition containing the compound of the present disclosure and a resin on a substrate. In the optical filter of the present disclosure, the compound of the present disclosure is preferably contained in an amount of 0.1 to 50 parts by mass, more preferably 0.3 to 5 parts by mass, per 1000 parts by mass of the resin. There are no particular restrictions on the resin that can be used in the optical filter, as long as it functions as an optical filter. Preferably, a resin that can form a film or optical filter layer with excellent transparency and mechanical properties is used. Examples of such resins include polyesters such as polyethylene terephthalate, cellulose esters such as cellulose diacetate, cellulose triacetate, and cellulose acetate butyrate, polyolefins such as polyethylene and polypropylene, polyvinyl compounds such as polyvinyl chloride, polyvinylidene chloride, vinyl chloride-vinyl acetate copolymers, and polystyrene, acrylic addition polymers such as polymethyl methacrylate, polycarbonates made from polycarbonate esters, and gelatin. From the viewpoints of cost, film quality, and transparency, polyesters, cellulose esters, and acrylic resins are preferred. From the viewpoints of film strength and uniformity, the weight-average molecular weight of the resin is preferably in the range of 10,000 to 1,000,000, and more preferably in the range of 20,000 to 500,000.

[0100] The optical filter of the present disclosure may further contain other components as described above in the composition of the present disclosure. Examples of other components include additives such as radical scavengers, antidegradants, and barbituric acid compounds. When additives are included, the content of the additives is preferably in the range of 1 to 30% by mass relative to the resin.

[0101] -Ultraviolet Absorber- From the viewpoint of improving lightfastness, the addition of an ultraviolet absorber to the optical filter of the present disclosure is effective. The ultraviolet absorber is not particularly limited, but examples thereof include substituted or unsubstituted benzoic acid esters such as resorcinol monobenzoate and methyl salicylate, cinnamic acid esters such as 2-oxy-3-methoxybutyl cinnamate, benzophenones such as 2,4-dioxybenzophenone, α,β-unsaturated ketones such as dibenzalacetone, coumarins such as 5,7-dioxycoumarin, carbostyrils such as 1,4-dimethyl-7-oxycarbostil, and azoles such as 2-phenylbenzimidazole and 2-(2-hydroxyphenyl)benzotriazole.

[0102] Plasticizers that can be used in the optical filters of the present disclosure are not particularly limited, but examples include polyhydric alcohol polyester compounds (hereinafter also referred to as "polyhydric alcohol ester plasticizers"), polycondensation ester compounds (hereinafter also referred to as "polycondensation ester plasticizers"), and carbohydrate compounds (hereinafter also referred to as "carbohydrate derivative plasticizers"). For polyhydric alcohol ester plasticizers, see paragraphs

[0081] to

[0098] of WO 2015 / 005398; for polycondensation ester plasticizers, see paragraphs

[0099] to

[0122] of the same publication; and for carbohydrate derivative plasticizers, see paragraphs

[0123] to

[0140] of the same publication, the contents of which are incorporated herein by reference.

[0103] (Thickness) The thickness of the optical filter of the present disclosure is usually 0.02 mm to 50 mm, but can be designed to a thickness outside this range depending on the application.

[0104] (Transmittance) The optical filter of the present disclosure only needs to have a transmittance in the wavelength range that it is to block functionally low enough to achieve the intended purpose, and from that viewpoint, the optical filter preferably has a light transmittance of 50% or less, more preferably 20% or less, and even more preferably 10% or less, at 580 nm, for example. Means for achieving the desired transmittance include adjusting the amount of the dye of the present disclosure added to the resin or adjusting the thickness of the optical filter.

[0105] The method for producing the optical filter of the present disclosure is not particularly limited, and the filter can be produced by the following methods. For example, when producing the optical filter, a composition containing the dye and resin of the present disclosure may be melted and extruded by a T-die method or an inflation method, or a composition containing the dye, resin, and organic solvent of the present disclosure may be formed into a film by a casting method.

[0106] As another production method, a polymerizable composition may be prepared by mixing the compound of the present disclosure, a monomer, an organic solvent, and a polymerization initiator, and the polymerizable composition may be applied to a suitable temporary support, polymerized by heat or light, and then formed into a film by peeling off the temporary support.

[0107] When an optical filter is formed on a substrate to form a laminate, a method of coating a solution or dispersion composition obtained by mixing the compound of the present disclosure, a resin, and an organic solvent onto the substrate to produce a laminate can also be used. The substrate is not particularly limited as long as it functions as an optical filter, and various plastic films or glass plates can be used, for example. A primer layer may be formed between the substrate and the optical filter layer to improve adhesion between the substrate and the optical filter layer. A protective layer may also be formed on the optical filter layer to protect the optical filter layer, impart drip resistance, etc. The protective layer can be formed, for example, by superimposing a 0.05 mm thick polyvinyl chloride film on the optical filter layer and heating and pressing it at 120°C to 140°C.

[0108] (Applications) The applications of the optical filter of the present disclosure are not particularly limited, but since the compound of the present disclosure can suppress the absorption decrease rate after exposure, it can be preferably used, for example, as a color filter for a liquid crystal display device and / or an organic EL display device.

[0109] A preferred embodiment of the compound of the present disclosure has excellent radical resistance and can therefore be used in applications other than optical filters. Examples include applications for writing instruments, particularly ballpoint pen inks, stamp inks, printing inks, inkjet inks, clothing dyeing, cell dyeing, blood detection, fluorescent dyes, pressure-sensitive, heat-sensitive, and temperature-sensitive indicators, optical recording materials, cosmetics, eyeglass lenses, contact lenses, and hair dyes. In particular, eyeglass lenses and contact lenses are preferred.

[0110] <Eyeglass Lens> The eyeglass lens of the present disclosure contains the compound of the present disclosure described above. There are no particular limitations on the resin that can be used in the eyeglass lens of the present disclosure, as long as it satisfies the physical properties required for eyeglass lenses, such as transparency, refractive index, processability, and hardness after curing. The resin may be a thermoplastic resin or a thermosetting resin. Examples of thermoplastic resins that can be used in eyeglass lenses include polycarbonate (PC). Examples of thermosetting resins include urethane resins and episulfide resins. As the urethane resin, a thiourethane resin is preferred. As the resin, a thiourethane resin is preferred from the viewpoint of a high refractive index, and a polycarbonate resin is preferred from the viewpoint of good transparency. That is, the resin in the eyeglass lens of the present disclosure is preferably at least one selected from the group consisting of a thiourethane resin and a polycarbonate resin.

[0111] For details of the thiourethane resins and episulfide resins suitable as resins for eyeglass lenses of the present disclosure, reference can be made to the descriptions in JP-A-2009-256692, JP-A-2007-238952, JP-A-2009-74624, JP-A-2015-212395, and JP-A-2016-84381.

[0112] The spectacle lens of the present disclosure may contain only one type of resin, or may contain two or more types. The content of the resin in the spectacle lens of the present disclosure is not particularly limited, and is, for example, preferably 30% by mass to 99.99% by mass, more preferably 50% by mass to 99.99% by mass, and even more preferably 60% by mass to 99.99% by mass, relative to the total mass of the spectacle lens. When the content of the resin in the spectacle lens of the present disclosure is within the above range, a lightweight and thin lens can be produced.

[0113] The eyeglass lenses of the present disclosure may contain other components in addition to the resin, such as ultraviolet absorbers, plasticizers, anti-degradants (e.g., antioxidants, peroxide decomposers, radical inhibitors, metal deactivators, acid scavengers, amines), dyes, internal mold release agents, deodorizers, etc.

[0114] The manufacturing method of the eyeglass lens of the present disclosure is not particularly limited as long as it can produce the eyeglass lens of the present disclosure described above. For example, when the resin contained in the eyeglass lens is a thermoplastic resin, the eyeglass lens of the present disclosure can be manufactured by kneading a resin composition containing the resin, a specific ultraviolet absorber, and, if necessary, other optional ultraviolet absorbers and other additives using a melt extruder, molding the kneaded mixture into pellets, and applying a known molding method such as injection molding to the obtained pelletized resin composition. For example, when the resin contained in the eyeglass lens is a thermosetting resin, the eyeglass lens of the present disclosure can be manufactured by preparing a resin composition containing a monomer that is a resin precursor, the compound of the present disclosure described above, a polymerization catalyst (e.g., dibutyltin dichloride), and, if necessary, other optional ultraviolet absorbers and other additives, filling the obtained resin composition into a mold (forming die), and curing it by heating.

[0115] <Contact Lenses> The contact lenses of the present disclosure contain the compound of the present disclosure described above. The compound of the present disclosure functions as a dye and has good heat resistance, making it suitable for use in contact lenses that are always used in a wet state. The contact lenses may be hard or soft contact lenses. The contact lenses of the present disclosure are not particularly limited in terms of their components other than the compound of the present disclosure described above, and can be used in combination with known components used in contact lenses. Examples of components that may be used in combination with contact lenses include the following materials. In addition to the polymerizable compound, other components include ultraviolet absorbers, polymerization initiators, sensitizers, polymerization inhibitors, crosslinking agents, plasticizers, and anti-degradants (e.g., antioxidants, peroxide decomposers, radical inhibitors, metal deactivators, acid scavengers, amines, etc.). Examples of the polymerizable compound include (meth)acrylate, alkyl (meth)acrylate, hydroxyalkyl (meth)acrylate, phenoxyalkyl (meth)acrylate, and alkylene glycol (meth)acrylic acid, and more specifically, examples thereof include methacrylic acid (MAA), hydroxyethyl methacrylate (HEMA), ethylene glycol dimethacrylate (ED), 2-hydroxy-3-phenoxypropyl acrylate (HPPA), phenoxyethyl acrylate (POEA), phenoxyethyl methacrylate (POEMA), benzyl acrylate (BA), and lauryl methacrylate (LMA). Among these, preferred polymerizable compounds include hydroxyethyl methacrylate (HEMA), ethylene glycol dimethacrylate (ED), and the like, which are polymerizable compounds having a carbonyl group and a hydroxy group in the molecule, and 2-hydroxyethyl methacrylate is more preferred.

[0116] The compound of the present disclosure is useful as a dye, and since the dye of the present disclosure has excellent optical properties, it is suitable for use in various applications including dyes. Examples of preferred applications are as described above in the composition of the present disclosure.

[0117] The present disclosure will be described in detail below using examples, but the present disclosure is not limited thereto. In these examples, "%" and "parts" mean "% by mass" and "parts by mass", respectively, unless otherwise specified. In addition, in polymer compounds, unless otherwise specified, the molecular weight is the weight average molecular weight (Mw), and the ratio of the constituent units is the molar percentage. The weight average molecular weight (Mw) is a value measured as a polystyrene equivalent value by gel permeation chromatography (GPC).

[0118] Example 1 Synthesis of Exemplary Compound S-7 According to the synthesis scheme below, 1-(2-hydroxyethyl)-2,3,3-trimethyl-3H-indolium bromide (represented as compound (A) in the synthesis scheme below) and (E)-1-phenyl-5-((E)-3-(phenylamino)allylidene)pyrimidine-2,4,6(1H,3H,5H)trione (represented as compound (B) in the synthesis scheme below) were synthesized.

[0119]

[0120]

[0121] A mixture of 0.92 g of compound (A), 1.00 g of compound (B), 3 mL of acetonitrile, and 3 mL of N,N-dimethylformamide was stirred at room temperature, and 1.0 mL of methacrylic anhydride and 0.46 mL of triethylamine were added, followed by stirring at room temperature for 4 hours. 0.42 mL of triethylamine was then added, and the mixture was stirred at room temperature for 2 hours and then allowed to stand overnight. 6 mL of distilled water was added, and the supernatant was removed. The residue was purified by silica gel chromatography. 3 mL of methanol was added to the obtained product, and the precipitated crystals were collected by filtration and dried to obtain 400 mg of compound S-7. １ H-NMR (DMSO-d ６) δ 10.98 & 10.96 (s, 1H), 8.21-8.06 (m, 2H), 7.74 & 7.59 (t, 1H), 7.52-7.20 (m, 8H), 7.12 (t, 1H), 6.30 & 6.19 (d, 1H), 5.84 & 5.81 (s, 1H), 5.57 & 5.55 (s, 1H), 4.50-4.30 (m, 4H), 1.70 & 1.67 (s, 3H), 1.59 (s, 6H) Compound S-7 was a mixture of geometric isomers. For compound S-7, 3.0 × 10 －５ The sample solution was diluted with chloroform to a concentration of 1 mol / L, and the absorbance was measured using a spectrophotometer (UV-3600 Plus, Shimadzu Corporation) in a 1 mm quartz cell. The maximum absorption wavelength (λmax) was measured from the absorption spectrum of the sample solution. The molar extinction coefficient can be calculated using the Lambert-Beer equation: ε = A / c × d, where c is the molar concentration, d is the thickness (cm) of the solution layer, and A is the absorbance. In other words, ε can be calculated by placing a solution of known molar concentration in a 1 cm long cell and measuring its absorbance A. The half-width represents the difference between two wavelengths that give an absorbance that is half the absorbance at the maximum absorption wavelength. In other words, the two wavelengths λA and λB (unit: nm) that give an absorbance of A / 2 for absorbance A at the maximum absorption wavelength are calculated, and the difference λA - λB (unit: nm) is the half-width. Maximum absorption wavelength: 564 nm (chloroform) Half width: 38 nm Molar absorption coefficient: 156,000

[0122] Example 2 Synthesis of Exemplary Compound S-17 According to the synthesis scheme below, 1-(2-methacryloyloxy)ethyl)-2,3,3-trimethyl-3H-indolium bromide (represented as compound (C) in the synthesis scheme below) and (E)-1,2-dibenzyl-4-(3-(phenylamino)allylidene)pyrazolidine-3,5-dione (represented as compound (D) in the synthesis scheme below) were synthesized.

[0123]

[0124]

[0125] 1.1 g of compound (C), 1.3 g of compound (D), 5 mg of 2,6-di-tert-butyl-p-cresol, and 3 mL of acetonitrile were stirred at room temperature. To this mixture, 0.31 mL of acetic anhydride and 0.91 mL of triethylamine were added, successively. 3 mL of acetonitrile was further added, and the mixture was stirred at room temperature for 2 hours and then allowed to stand for 2 days. 9 mL of distilled water was added to the reaction mixture, and the supernatant was removed. 100 mL of ethyl acetate was added to the residue to dissolve it, and approximately 3 g of magnesium sulfate was added thereto. The mixture was filtered, concentrated, and purified by silica gel chromatography to obtain 570 mg of compound S-17. １ H-NMR (DMSO-d ６ ) δ8.08 (t, 1H), 7.75 (d, 1H), 7.66 (d, 1H), 7.46 (d, 1H), 7.38-7.19 (m, 12H), 7.09 (t, 1H), 6.22 (d, 1H), 5.82 (s, 1H), 5.55 (s, 1H), 4.66 (s, 4H), 4.43 (t, 2H), 4.35 (t, 2H), 1.69 (s, 3H), 1.58 (s, 6H) Maximum absorption wavelength 549 nm (chloroform) Half width 39 nm Molar extinction coefficient 83600

[0126] Example 3: Synthesis of exemplary compound S-8

[0127]

[0128] A mixture of 1.32 g of compound (E), 0.88 g of compound (B), 3 mL of acetonitrile, and 3 mL of N,N-dimethylformamide was stirred at room temperature, and 0.31 mL of acetic anhydride and 0.88 mL of triethylamine were added. After stirring at room temperature for 4 hours, 6 mL of distilled water was added and the supernatant was removed. The residue was purified by silica gel chromatography. 5 mL of methanol was added to the obtained product, and the mixture was stirred at 50°C for 30 minutes. The precipitated crystals were collected by filtration and dried to obtain 430 mg of compound S-8. １H-NMR (DMSO-d6) δ 11.00 & 10.91 (s, 1H), 8.23-8.09 (m, 2H), 7.69-7.34 (m, 7H), 7.33-7.10 (m, 7H), 7.67 & 6.66 (t, 1H), 6.22 & 6.06 (d, 1H), 5.81 & 5.76 (d, 1H), 5.33-5.20 (m, 3H), 1.67 (s, 6H) Compound S-8 was a mixture of geometric isomers. Maximum absorption wavelength 565 nm (chloroform) Half width 38 nm Molar extinction coefficient 165,000

[0129] Example 4 Synthesis of Exemplary Compound S-12 According to the synthesis scheme below, 1,3-diethyl-5-((E)-4-((E)-1-(2-hydroxyethyl)-3,3-dimethylindolin-2-ylidene)-2-buten-1-ylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (referred to as compound (G) in the synthesis scheme below) was synthesized.

[0130]

[0131] A mixture of 0.85 g of compound (A), 0.99 g of compound (F), and 6 mL of acetonitrile was stirred at room temperature, and 0.28 mL of acetic anhydride and 0.46 mL of triethylamine were added. The mixture was stirred at room temperature for an additional hour, then the stirring was stopped and the mixture was left overnight. 6 mL of distilled water was added and the mixture was stirred, and the precipitated crystals were collected by filtration. The obtained crystals were purified by silica gel chromatography to obtain 360 mg of compound (G). A mixture of 255 mg of compound (G), 2.4 mL of tetrahydrofuran (THF), and 0.11 mL of 2-isocyanatoethyl methacrylate was stirred at room temperature. 1 drop of dibutyltin dilaurate was added to the mixture and the mixture was stirred at room temperature for 3 hours. 2.5 mL of methanol and 2.5 mL of distilled water were added to the mixture, and the precipitated crystals were collected by filtration. 5 mL of methanol was added to the obtained crystals, and the mixture was stirred at room temperature, then collected by filtration, and dried to obtain 310 mg of compound S-12. １ H-NMR (DMSO-d ６) δ 8.18-8.08 (m, 2H), 7.73 (t, 1H), 7.48 (d, 1H), 7.34-7.25 (m, 2H), 7.19 (d, 1H), 7.12 (t, 1H), 6.21 (d, 1H), 6.01 (s, 1H) , 5.63 (s, 1H), 4.36-4.20 (m, 4H), 3.92 (t, 2H), 3.88-3.79 (m, 4H), 3.15 (q, 2H) 1.83 (s, 3H), 1.62 (s, 6H), 1.10 (t, 6H) Maximum absorption wavelength 560nm (Chloroform) Half width 39nm Molar extinction coefficient 126,000

[0132] Example 5 (Preparation of Composition) A composition (second embodiment of the composition) of the present disclosure containing a monomer and a polymerization initiator was prepared using the compound S-7 of Example 1 obtained above according to the following formulation: 0.02 parts of compound S-7, the dye of Example 1, and 0.3 parts of phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (Fujifilm Wako Pure Chemical Industries, Ltd.: photopolymerization initiator) were added to 30 parts of 2-hydroxyethyl methacrylate (monomer), and the mixture was stirred with a magnetic stirrer for 30 minutes. The resulting mixture was filtered through a 0.45 μm filter (PTFE, manufactured by Advantec Toyo Co., Ltd.) to prepare a polymerizable composition (second embodiment of the composition).

[0133] (Absorbance Decrease Rate After Exposure) A 100 μm-thick silicone film with a 1 cm × 1 cm central cutout was placed on a glass substrate (2.5 cm × 2.5 cm, Eagle XG, manufactured by AXEL), and two drops (0.4 mL) of the polymerizable composition of Example 5 were dropped into the center of the film using a dropper. Another glass substrate (2.5 cm × 2.5 cm, Eagle XG, manufactured by AXEL) was then placed on top of the film to obtain a laminate having the polymerizable composition in the glass substrate. The transmission spectrum was measured using a spectrophotometer (Shimadzu Corporation, UV3600) to measure the absorbance in the initial state. The results are shown in the "Initial State" column in Table 3 below. After the laminate was formed, the resulting laminate was irradiated with a UV lamp (manufactured by HOYA-SCHOTT, EXECURE 3000-W, 100 mW / cm ２, 30 seconds). Thereafter, the transmission spectrum after exposure was measured again, and the absorbance of the laminate after exposure was measured. The results are shown in the "After exposure" column in Table 3 below. The absorbance reduction rate after exposure was calculated according to the following formula. The results are shown in Table 3 below. Absorbance reduction rate after exposure (%) = [(absorbance in initial state) - (absorbance after exposure)] / (absorbance in initial state) x 100

[0134] (Evaluation of dye fixation) A 100 μm thick silicon film with a 1 cm × 1 cm central cutout was placed on a glass substrate (2.5 cm × 2.5 cm, Eagle XG, manufactured by AXEL), and two drops (0.4 mL) of the polymerizable composition of Example 5 were dropped onto the central portion using a dropper to obtain a sample having the polymerizable composition on the glass substrate. The obtained sample was irradiated with a UV lamp (manufactured by HOYA-SCHOTT, EXECURE 3000-W, 100 mW / cm ２ The glass substrate having the photocured polymerizable composition was then immersed in a petri dish containing tetrahydrofuran and left at room temperature for 30 minutes, then removed and washed with tetrahydrofuran. The washed glass substrate was visually observed for color change before and after immersion in tetrahydrofuran. The results were classified as follows: Classification A: No color change was observed visually. B: A color change was observed visually, and a decrease in color density was evident after immersion. C: The color of the dye disappeared visually after immersion, and the substrate was almost transparent.

[0135] Examples 6 to 8, Comparative Examples 1 to 4 Polymerizable compositions were prepared and evaluated in the same manner as in Example 5, except that the compounds produced in Examples 2 to 4 and comparative compounds H-1 to H-4 were used instead of compound S-7 in Example 5. The compounds used and the results are shown in Table 3 below.

[0136]

[0137]

[0138] As is clear from Table 3, compositions containing the compounds (dyes) of the Examples exhibit a small rate of decrease in absorbance after exposure. Furthermore, in addition to the small rate of decrease in absorbance after exposure, compositions containing the compounds (dyes) of the Examples exhibit no change in the maximum absorption wavelength between the initial state and after exposure, demonstrating excellent radical resistance. Furthermore, compositions containing the compounds (dyes) of the Examples exhibit excellent dye fixation.

[0139] From the above evaluation results, the compounds (dyes) of the examples have a small rate of decrease in absorbance after exposure, good radical resistance and dye fixation, and can be suitably used in both resin-containing compositions and polymerizable compositions, and have a wide range of applications.

[0140] According to one embodiment of the present disclosure, there is provided a novel compound or a method for producing the novel compound. According to another embodiment of the present disclosure, there is provided a dye having a small rate of decrease in absorbance after exposure, a composition containing the novel compound, an optical filter, an eyeglass lens, or a contact lens each containing the novel compound.

[0141] Although the present disclosure has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present disclosure. This application is based on a Japanese patent application (Patent Application No. 2023-146388) filed on September 8, 2023, the contents of which are incorporated herein by reference.

Claims

1. A compound represented by the following general formula (1): １ -L １ -P １ (1) In general formula (1), M １ represents a group obtained by removing any one hydrogen atom from a compound represented by the following general formula (2): １ represents a single bond or a divalent linking group. １ represents a group represented by any one of the following formulas (P-1) to (P-10). In general formula (2), X １ is an oxygen atom, a sulfur atom, CR ｘ１ R ｘ２ Or NR ｘ３ Represents ｘ１ , R ｘ２ and R ｘ３ R each independently represents a hydrogen atom or a substituent. １ represents an alkyl group. １ ~V ４ each independently represents a hydrogen atom or a substituent. １ ~V ４ At least two of may be bonded to each other via a linking group or without a linking group to form a ring. ５ ~V ８ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. １ represents an acidic nucleus. １ may be cyclic or open-chain. In formulas (P-1) to (P-10), * represents L １ represents the bonding position with 2. The compound according to claim 1, wherein the partial structure represented by the following general formula (2-A) in the general formula (2) is represented by any one of the following general formulas (1-a) to (1-w). In the above general formula, * １ is V in general formula (2) ８ represents the bonding position with the carbon atom to which X is bonded. ２ and X ３ Each independently represents an oxygen atom or a sulfur atom. １ represents an electron-withdrawing group. １ R represents a hydrogen atom, a carbamoyl group, an alkyl group, an aryl group, a cyano group, a carboxy group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a halogen atom, an amino group, an acylamino group, an alkylsulfonyl group, an arylsulfonyl group, or a sulfo group. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ and R Ａ６ each independently represents a hydrogen atom or a substituent.

3. X in the general formula (2) １ is CR ｘ１ R ｘ２ and R ｘ１ and R ｘ２ The compound of claim 2 , wherein each independently represents an alkyl group.

4. A dye which is the compound according to any one of claims 1 to 3.

5. A composition comprising the compound according to any one of claims 1 to 3 and a resin.

6. A composition comprising the compound according to any one of claims 1 to 3, a monomer, and a polymerization initiator.

7. An optical filter comprising the compound according to any one of claims 1 to 3.

8. A spectacle lens comprising the compound according to any one of claims 1 to 3.

9. A contact lens comprising the compound according to any one of claims 1 to 3.

10. A method for producing a compound represented by the following general formula (1) using a compound represented by the following general formula (3): １ -L １ -P １ (1) In general formula (1), M １ represents a group obtained by removing any one hydrogen atom from a compound represented by the following general formula (2): １ represents a single bond or a divalent linking group. １ represents a group represented by any one of the following formulas (P-1) to (P-10). In general formula (2), X １ is an oxygen atom, a sulfur atom, CR ｘ１ R ｘ２ Or NR ｘ３ Represents R ｘ１ , R ｘ２ and R ｘ３ R each independently represents a hydrogen atom or a substituent. １ represents an alkyl group. １ ~V ４ each independently represents a hydrogen atom or a substituent. １ ~V ４ At least two of may be bonded to each other via a linking group or without a linking group to form a ring. ５ ~V ８ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. １ represents an acidic nucleus. １ may be cyclic or open-chain. In formulas (P-1) to (P-10), * represents L １ represents the bonding position with In general formula (3), R １０ represents a hydrogen atom or an acetyl group. ６ ~V ８ and A １ Each represents V in general formula (2). ６ ~V ８ and A １ It has the same meaning as:

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