Colorant composition, compound, colorant, blue-blocking agent, polymer, cured product, and optical material

Abstract

Provided are: a colorant composition containing a colorant represented by formula 1; a compound; a colorant; a blue-blocking agent; a polymer; a cured product; and an optical material.　In formula 1, R1 and R2 each independently represent an alkyl group or an aryl group, R3, R5 and R6 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and R4 represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. R5 and R6 may be bonded to each other to form a six-membered ring. However, at least one of R1-R6 is a group containing a polymerizable group that has an ethylenically unsaturated bond.

Description

Dye composition, compound, dye, blue screening agent, polymer, cured product, and optical material

[0001] The present disclosure relates to a dye composition, a compound, a dye, a blue-shielding agent, a polymer, a cured product, and an optical material.

[0002] Dyes are used to display colors by utilizing reflected or transmitted light in fields such as photographic photosensitive materials, textile dyeing materials, liquid crystal display devices, inkjet printing, etc. Furthermore, high-energy visible light, also known as blue light, is thought to have the potential to affect the human body (especially the eyes), and therefore dyes that absorb high-energy visible light are used in eyeglass lenses, protective films, etc.

[0003] Resin compositions, dye compounds, and the like that have high absorbance in at least the wavelength region of 350 nm to 450 nm and excellent light resistance and heat resistance are known (for example, Patent Document 1). Also known are polymerizable compositions and the like that are excellent in blocking light with a wavelength of around 400 nm and that can produce polymers that have excellent light resistance (for example, Patent Document 2).

[0004] Patent Document 1: International Publication No. 2020 / 235674 Patent Document 2: International Publication No. 2022 / 039120

[0005] As a dye that absorbs high-energy visible light, a dye with a relatively low molecular weight can sometimes cause problems such as diffusion or bleeding out after molding into optical films, lenses, etc. Furthermore, when attempting to mix with other materials at high concentrations, problems such as phase separation or precipitation can occur due to poor compatibility.

[0006] An object of the present disclosure is to provide a dye composition, a compound, a dye, a blue light blocking agent, a polymer, a cured product, and an optical material that have high absorbance to blue light and excellent light resistance and solvent resistance.

[0007] Specific means for solving the problems include the following aspects: <1> A dye composition containing a dye represented by the following formula 1:

[0008]

[0009] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of R is a group containing a polymerizable group having an ethylenically unsaturated bond. １ and R ２ and each independently represent an alkyl group or a phenyl group. １ ~R ６ The dye composition according to <1> or <2>, wherein at least one of the above is a group containing a (meth)acryloyloxy group or a vinylphenyl group as the group containing a polymerizable group. <4> The dye composition according to any one of <1> to <3>, containing a polymerizable compound that is a compound different from the dye. <5> The dye composition according to any one of <1> to <4>, containing a copolymer of the dye and a polymerizable compound that is a compound different from the dye. <6> The dye composition according to any one of <1> to <5>, containing a photopolymerization initiator. <7> The dye composition according to any one of <1> to <6>, containing a resin. <8> The dye composition according to any one of <1> to <7>, containing a light-absorbing compound having an absorption maximum wavelength that is shorter in wavelength than the dye. <9> A compound represented by the following formula 1:

[0010]

[0011] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of the above is a group containing a polymerizable group having an ethylenically unsaturated bond. <10> A dye represented by the following formula 1:

[0012]

[0013] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of the above is a group containing a polymerizable group having an ethylenically unsaturated bond. <11> A blue screening agent represented by the following formula 1:

[0014]

[0015] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６<12> A polymer comprising a structural unit derived from the compound according to <9>. <13> A cured product obtained from the dye composition according to any one of <1> to <8>. <14> An optical material comprising the cured product according to <13>.

[0016] According to embodiments of the present disclosure, it is possible to provide a dye composition, a compound, a dye, a blue light blocking agent, a polymer, a cured product, and an optical material that have high absorbance to blue light and excellent light resistance and solvent resistance.

[0017] FIG. 1 is an explanatory diagram illustrating the general formula of the dye.

[0018] The present disclosure will be described in detail below. The following description of the components may be based on representative embodiments of the present disclosure, but the present disclosure is not limited to the above embodiments.

[0019] In the present disclosure, the use of "to" indicating a numerical range means that the numerical values ​​before and after it are included as the upper and lower limits. 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 a value shown in the examples.

[0020] In the present disclosure, compounds that are not specified as substituted or unsubstituted may have any substituent within the scope that does not impair the effects of the present disclosure.

[0021] In the present disclosure, when a layer contains a plurality of substances corresponding to each component, the amount of each component in the composition means the total amount of the plurality of substances present in the composition, unless otherwise specified.

[0022] In the present disclosure, a combination of preferred aspects is a more preferred aspect.

[0023] <Dye Composition> The dye composition of the present disclosure contains a dye represented by the following formula 1 (hereinafter also referred to as a specific dye). The dye composition of the present disclosure may further contain another dye different from the specific dye, a polymerizable compound, a polymer, a resin, a photopolymerization initiator, an ultraviolet absorber, a light-absorbing compound, and other components, as necessary. Examples of other components include a solvent, a catalyst, a surfactant, etc.

[0024] (Dye) The present inventors have discovered that a specific dye, which is a compound having a structure in which a pyrazolidinedione skeleton and a pyrrole skeleton are linked by a methine group and a specific polymerizable group is arranged, as represented by Formula 1, has high absorbance in the wavelength range of 380 nm to 450 nm, is a polymerizable monomer, and has excellent light resistance and solvent resistance. Wavelengths of 380 nm to 450 nm fall within the wavelength range generally referred to as high-energy visible light, blue light, etc. The dye composition of the present disclosure contains a specific dye having a structure in which a pyrazolidinedione skeleton and a pyrrole skeleton are linked by a methine group and having a specific polymerizable group, as represented by Formula 1, and therefore has high absorbance for light with wavelengths of at least 380 nm to 450 nm, is a polymerizable composition, and has excellent light resistance and solvent resistance. Therefore, by using the dye composition of the present disclosure, it is possible to obtain, by a known molding method, a cured product, optical material, or the like that has high absorbance for light with wavelengths of 380 nm to 450 nm, excellent light resistance, and excellent solvent resistance because the specific dye, etc., is immobilized by a specific polymerizable group possessed by the specific dye. Specifically, for example, a material that blocks or suppresses ultraviolet (UV) and blue light (e.g., molded products such as glass, film or sheet, and lens) can be provided. Furthermore, by containing multiple dyes, including a specific dye and dyes that each absorb different wavelengths, it is possible to provide a material with a controlled wavelength range of transmitted light, such as a material that selectively transmits violet light, or a UV- and blue-light-blocking material that selectively transmits light in the wavelength range in which the photopolymerization initiator is active.

[0025] The dye composition of the present disclosure contains a specific dye. The specific dye is preferably a yellow-based dye having high absorbance at least in the wavelength range of 380 nm to 450 nm. Furthermore, a yellow-based dye having high absorbance in the wavelength range of 400 nm to 450 nm is even more preferable. The specific dye is preferably a yellow-based dye having a maximum absorption wavelength in the wavelength range of 380 nm to 450 nm. Furthermore, a yellow-based dye having a maximum absorption wavelength in the wavelength range of 400 nm to 450 nm is even more preferable. Therefore, the specific dye absorbs blue light. According to the Japan Ophthalmological Society, blue light is blue light with a wavelength of approximately 380 nm to 495 nm. Furthermore, the specific dye may have higher absorbance in the wavelength range of 380 nm to 450 nm than at other wavelengths, but may also have lower transmittance in the wavelength range of 380 nm to 450 nm than at other wavelengths. The specific dye may also include dyes and pigments.

[0026]

[0027] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of the groups is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0028] R １ ~R ６ At least one of R is a group containing a polymerizable group having an ethylenically unsaturated bond, and the group containing a polymerizable group having an ethylenically unsaturated bond will be described later. １ and R ２ The alkyl group in the formula (I) may be either an unsubstituted alkyl group or a substituted alkyl group.

[0029] Examples of the unsubstituted alkyl group include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, and a cyclohexyl group. An alkyl group having 1 to 12 carbon atoms is preferred, and an alkyl group having 1 to 8 carbon atoms is more preferred.

[0030] Examples of the substituent of the substituted alkyl group include substituents included in the following substituent group A. (Substituent group A) Halogen atoms, alkyl groups, cycloalkyl groups, aralkyl groups, alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, cyano groups, hydroxy groups, nitro groups, carboxyl groups (which may be in the form of a salt), alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, acyloxy groups, carbamoyloxy groups, sulfonyloxy groups, alkoxycarbonyloxy groups, aryloxycarbonyloxy groups, amino groups (including anilino groups), alkylamino groups, acylamino groups, aminocarbonylamino groups, alkylcarbonylamino groups, alkoxy ... groups, aryloxycarbonylamino groups, sulfamoylamino groups, alkylsulfonylamino groups, arylsulfonylamino groups, sulfonamide groups, mercapto groups, alkylthio groups, arylthio groups, heterocyclic thio groups, sulfamoyl groups, sulfo groups (which may be in the form of a salt), alkylsulfinyl groups, arylsulfinyl groups, alkylsulfonyl groups, arylsulfonyl groups, acyl groups, aryloxycarbonyl groups, alkoxycarbonyl groups, carbamoyl groups, imido groups, phosphino groups, phosphinyl groups, phosphinyloxy groups, phosphinylamino groups, silyl groups, etc.

[0031] Among the substituent group A, preferred examples of the substituent of the substituted alkyl group include a halogen atom, an alkyl group, an aryl group, an alkoxy group, an acyl group, and a hydroxy group.

[0032] The substituted alkyl group is preferably an alkyl group having a total of 1 to 12 carbon atoms, and examples thereof include a benzyl group, a hydroxybenzyl group, and a methoxyethyl group.

[0033] In addition, R １ and R ２When both represent alkyl groups, the alkyl groups may be the same or different.

[0034] R １ and R ２ The aryl group in may be either an unsubstituted aryl group or a substituted aryl group.

[0035] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, such as a phenyl group.

[0036] Examples of the substituent of the substituted aryl group include the substituents included in the above-mentioned substituent group A. Preferred examples of the substituent of the substituted aryl group include a halogen atom (e.g., a chlorine atom, a bromine atom, an iodine atom), a hydroxy group, a carboxy group, a sulfonamide group, an amino group, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; e.g., methyl, ethyl, normal propyl, isopropyl), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms; e.g., methoxy, ethoxy, normal propoxy, isopropoxy), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; e.g., methoxycarbonyl, ethoxycarbonyl, normal propoxycarbonyl, isopropoxycarbonyl), a sulfonyloxy group, and a monovalent group in which at least two of these are linked together.

[0037] The substituted aryl group substituted with a substituent is preferably an aryl group having a total of 6 to 18 carbon atoms, and examples thereof include a 4-chlorophenyl group, a 2,5-dichlorophenyl group, a hydroxyphenyl group, a 4-carboxyphenyl group, a 3,5-dicarboxyphenyl group, a 4-methanesulfonamidophenyl group, a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-(2-hydroxyethoxy)phenyl group, an N,N-dimethylaminophenyl group, a 4-(N-carboxymethyl-N-ethylamino)phenyl group, a 4-ethoxycarbonylphenyl group, and a 4-methanesulfonyloxyphenyl group.

[0038] In addition, R １ and R ２ When both represent aryl groups, the aryl groups may be the same or different.

[0039] R ３ , R ４ , R ５ and R ６ may be unsubstituted or substituted with a substituent. ３ , R ４ , R ５ and R ６ Examples of the substituent in the group R include those included in the group A of substituents. ３ , R ５ and R ６ The substituent of R is preferably an alkyl group or an aryl group. ４ The substituent of is preferably an alkyl group, an aryl group, or an amino group.

[0040] R ３ , R ５ and R ６ It is preferable that each of R independently represents a hydrogen atom, an alkyl group, or an aryl group.

[0041] R ３ , R ５ and R ６ The alkyl group in the formula (I) may be either an unsubstituted alkyl group or a substituted alkyl group.

[0042] Examples of the unsubstituted alkyl group include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a butyl group, and a 2-ethylhexyl group. An alkyl group having 1 to 12 carbon atoms is preferred, and an alkyl group having 1 to 8 carbon atoms is more preferred.

[0043] R ３ , R ５ and R ６ Examples of the substituent on the substituted alkyl group in the formula (I) include the substituents included in the above-mentioned substituent group A. Preferred examples of the substituent on the substituted alkyl group include a phenyl group, a carboxy group, a hydroxy group, etc. As the substituted alkyl group substituted with a substituent, an alkyl group having a total of 1 to 8 carbon atoms is preferred, and examples thereof include a benzyl group, a carboxymethyl group, a hydroxymethyl group, etc.

[0044] In addition, R３ , R ５ and R ６ When both represent alkyl groups, the alkyl groups may be the same or different.

[0045] R ３ , R ５ and R ６ The aryl group in may be either an unsubstituted aryl group or a substituted aryl group.

[0046] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, such as a phenyl group.

[0047] R ３ , R ５ and R ６ Examples of the substituent of the substituted aryl group in the formula (I) include the substituents included in the above-mentioned Substituent Group A. Preferred examples of the substituent of the substituted aryl group include a halogen atom (e.g., a chlorine atom, a bromine atom, an iodine atom), a hydroxy group, a carboxy group, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; e.g., methyl, ethyl, normal propyl, isopropyl), and the like.

[0048] The substituted aryl group substituted with a substituent is preferably an aryl group having a total of 6 to 10 carbon atoms, and examples thereof include a 4-chlorophenyl group, a 2,5-dichlorophenyl group, a hydroxyphenyl group, a carboxyphenyl group, a 3,5-dicarboxyphenyl group, and a 4-methylphenyl group.

[0049] R ５ and R ６ are each independently an alkyl group or an aryl group, from the viewpoint of light resistance and solvent resistance, R ３ is preferably a hydrogen atom. ３ , R ５ and R ６ When both represent aryl groups, the aryl groups may be the same or different.

[0050] R ４ is preferably a hydrogen atom, an alkyl group, an aryl group, or an amino group.

[0051] R４ The alkyl group in the formula (I) may be either an unsubstituted alkyl group or a substituted alkyl group.

[0052] Examples of the unsubstituted alkyl group include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, and a cyclohexyl group. An alkyl group having 1 to 8 carbon atoms is preferred, and an alkyl group having 1 to 4 carbon atoms is more preferred.

[0053] R ４ Examples of the substituent of the substituted alkyl group in the formula (I) include the substituents included in the above-mentioned substituent group A. Preferred examples of the substituent of the substituted alkyl group include a phenyl group, a carboxy group, a hydroxy group, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; for example, methyl, ethyl, normal propyl, isopropyl), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms; for example, methoxy, ethoxy, normal propoxy, isopropoxy), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; for example, methoxycarbonyl, ethoxycarbonyl, normal propoxycarbonyl, isopropoxycarbonyl), an alkylamino group (preferably an alkylamino group having 1 to 4 carbon atoms; for example, dimethylamino group), an alkylcarbonylamino group (preferably an alkylcarbonylamino group having 1 to 4 carbon atoms; for example, methylcarbonylamino group), a cyano group, and a monovalent group in which at least two of these are linked together.

[0054] The substituted alkyl group substituted with a substituent is preferably an alkyl group having a total of 1 to 18 carbon atoms, and examples thereof include a benzyl group, a carboxybenzyl group, a hydroxybenzyl group, a methoxycarbonylethyl group, an ethoxycarbonylmethyl group, a 2-cyanoethyl group, a 2-propioxylaminoethyl group, a dimethylaminomethyl group, a methylcarbonylaminopropyl group, a di(methoxycarbonylmethyl)aminopropyl group, and a phenacyl group.

[0055] R ４ The aryl group in may be either an unsubstituted aryl group or a substituted aryl group.

[0056] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, such as a phenyl group.

[0057] R ４ Examples of the substituent of the substituted aryl group in the formula (I) include the substituents included in the above-mentioned Substituent Group A. Preferred examples of the substituent of the substituted aryl group include a halogen atom (e.g., a chlorine atom, a bromine atom, an iodine atom), a hydroxy group, a carboxy group, a sulfonamide group, an amino group, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; e.g., methyl, ethyl, normal propyl, isopropyl), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms; e.g., methoxy, ethoxy, normal propoxy, isopropoxy), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; e.g., methoxycarbonyl, ethoxycarbonyl, normal propoxycarbonyl, isopropoxycarbonyl), a sulfonyloxy group, and a monovalent group in which at least two of these are linked together.

[0058] The substituted aryl group substituted with a substituent is preferably an aryl group having a total of 6 to 22 carbon atoms, such as a 4-chlorophenyl group, a 2,5-dichlorophenyl group, a hydroxyphenyl group, a 2,5-methoxyphenyl group, a 2-methoxy-5-ethoxycarbonylphenyl group, a 4-ethyloxycarbonylphenyl group, a 4-ethoxycarbonylphenyl group, a 4-butoxycarbonylphenyl group, a 4-octyloxycarbonylphenyl group, a 4-carboxyphenyl group, a 3,5-dicarboxyphenyl group, a 4-methanesulfonamidophenyl group, a 4-methylphenyl group, a 4-methoxyphenyl group, group, a 4-ethoxyphenyl group, a 4-(2-hydroxyethoxy)phenyl group, an N,N-dimethylaminophenyl group, an N,N-diethylaminophenyl group, a 4-(N-carboxymethyl-N-ethylamino)phenyl group, a 4-{N,N-di(ethoxycarbonylmethyl)amino}phenyl group, a 4-{di(ethoxycarbonylmethyl)amino}carbonylphenyl, a 4-ethoxycarbonylphenyl group, a 4-methanesulfonyloxyphenyl group, a 4-acetylsulfamoylphenyl, a 4-propionylsulfamoylphenyl, and a 4-methanesulfonamidophenyl group.

[0059] R ４ The amino group in may be either an unsubstituted amino group or a substituted amino group.

[0060] Examples of the substituent of the substituted amino group include the same groups as the substituent of the substituted alkyl group. The substituted amino group is preferably an alkylamino group in which one or two hydrogen atoms of the amino group are substituted with an alkyl group. Examples of the alkylamino group include a methylamino group, a dimethylamino group, a diethylamino group, and a pyrrolidino group. An alkylamino group having 1 to 8 carbon atoms is preferred, and an alkylamino group having 1 to 4 carbon atoms is more preferred.

[0061] R ５ and R ６ may be bonded to each other to form a 6-membered ring. ５ and R ６ The six-membered ring formed by bonding together is preferably a benzene ring.

[0062] In Formula 1, R １ and R ２ Preferably, each independently represents an alkyl group or a phenyl group. １ and R ２ Among them, R １ It is preferable that R is an alkyl group from the viewpoint of light resistance. １ represents an alkyl group, and R ２ It is more preferable that R represents an alkyl group or an aryl group. １ and R ２ It is more preferable that each of the groups independently represents an alkyl group, and it is particularly preferable that each of the groups independently represents an alkyl group having 1 to 8 carbon atoms or a benzyl group.

[0063] Furthermore, R in Formula 1 １ and R ２ Among these, R is the best in terms of light resistance and solvent resistance. １ and R ２ It is also preferable that all of R represent an aryl group. １ and R ２ It is more preferable that both of these represent a phenyl group.

[0064] R １ ~R ６ At least one of R in Formula 1 is a group containing a polymerizable group having an ethylenically unsaturated bond. １ ~R ６ Examples of the substituent represented by the formula (I) include the above-mentioned substituents and a group containing a polymerizable group having an ethylenically unsaturated bond (hereinafter also referred to as a group containing a polymerizable group).

[0065] R １ ~R ６ Any one or more of R may be a group containing a polymerizable group. １ ~R ６ The number of groups containing a polymerizable group among R can be determined depending on the application, purpose, etc. For example, in order to improve reactivity, １ ~R ６ Many of these groups can be groups containing polymerizable groups, while in order to adjust the physical properties of the reaction product, R １ ~R ６One of R may be a group containing a polymerizable group. １ and / or R ２ may be a group containing a polymerizable group, or R ３ ~R ６ may be a group containing a polymerizable group, or R １ or R ２ And, R ３ ~R ６ Any one or more of R may be a group containing a polymerizable group. ３ ~R ６ It is preferable that one or more of R be a group containing a polymerizable group. ４ is preferably a group containing a polymerizable group.

[0066] Examples of the group containing a polymerizable group include a group represented by the following formula 2: *-X ｔ -Y ｔ -Z ｔ Formula 2

[0067] In formula 2, X ｔ represents a single bond, an alkylene group, an arylene group, —O—, —OC(═O)—, —OC(═O)O—, or —OC(═O)NRx １ represents -, and Rx １ represents a hydrogen atom, an alkyl group, or an aryl group; Y ｔ represents a single bond or a divalent linking group; Z ｔ represents a polymerizable group having an ethylenically unsaturated bond.

[0068] Rx １ The alkyl group represented by is preferably an alkyl group having 1 to 30 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. １ The aryl group represented by is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Specific examples include a phenyl group, a p-tolyl group, and a naphthyl group. １ is preferably a hydrogen atom.

[0069] Y ｔ Examples of the divalent linking group represented by include a hydrocarbon group and a group in which two or more hydrocarbon groups are linked via a single bond or a linking group. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The cyclic aliphatic hydrocarbon group may be a monocyclic or fused ring. The cyclic aliphatic hydrocarbon group may have a crosslinked structure. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include the aforementioned substituent A. For example, an example of the substituent is a hydroxy group. Examples of the linking group linking the two or more hydrocarbon groups include -NH-, -S(=O) ２ -, -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -NHC(=O)-, -C ６ H ４ -(phenylene group), and -C(=O)NH-, and examples thereof include -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -NHC(=O)-, -C ６ H ４ It is preferably -(phenylene group) or -C(=O)NH-.

[0070] Z ｔ Examples of the polymerizable group having an ethylenically unsaturated bond represented by R include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group, and a (meth)acryloyloxy group and a vinylphenyl group are preferred. That is, the group containing a polymerizable group is １ ~R ６ At least one of the groups preferably contains a (meth)acryloyloxy group or a vinylphenyl group.

[0071] As a specific example of the specific dye, in formula 1-1 shown in FIG. 1, partial structure X or partial structure Y is preferably a group represented by the following formula. Here, partial structure X is a group on the left side of the methine group in the case shown in formula 1-1, and partial structure Y is a group on the right side of the methine group in the case shown in formula 1-1. Partial structure X is preferably any one of groups X-1 to X-15 shown below, and partial structure Y is preferably any one of groups Y-1 to Y-34 shown below. In each of the following formulas, * indicates a bonding position, and Me indicates a methyl group.

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] Specifically, the specific dye is preferably Compounds Z-1 to Z-149 shown in Tables 1 to 5 below, which are represented by combinations of the partial structure X and partial structure Y shown above. However, the present disclosure is not limited to the following specific examples.

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] Synthesis The specific dye can be synthesized by mixing a pyrazolidinedione represented by Formula 3 and an aldehyde represented by Formula 4 in an organic solvent under conditions ranging from room temperature (25°C) to reflux, as shown in the following scheme.

[0086]

[0087] As the organic solvent, for example, alcohol (for example, methanol, ethanol), acetonitrile, N,N-dimethylformamide (DMF), pyridine, acetic acid, acetic anhydride, etc. can be used.

[0088] In the synthesis, a catalyst may be added, such as piperidine, glycine, β-alanine, p-toluenesulfonic acid, or ammonium acetate.

[0089] After refluxing, the mixture may be cooled to room temperature (25°C) to precipitate. The precipitated solid may be collected by filtration and washed with an organic solvent. The same organic solvent as that used in the synthesis may be used for washing.

[0090] The specific dye may be contained in the dye composition singly or in a mixture of two or more types. The content of the specific dye in the dye composition is preferably 0.01% to 5% by mass, more preferably 0.1% to 2% by mass, based on the total solids content of the dye composition. In this specification, the total solids content refers to the total content of all components of the dye composition excluding the solvent constituting the dye composition. Since the specific dye has high absorbance, particularly in the wavelength range of 380 nm to 450 nm, when the content of the specific dye in the dye composition is within the above range, the dye has excellent blocking or suppressing functions for light with wavelengths of 380 nm to 450 nm. The specific dye can effectively block or suppress blue light.

[0091] (Polymerizable Compound) The dye composition of the present disclosure may contain the specific dye described above and a polymerizable compound (hereinafter also referred to as a polymerizable compound) that is a compound different from the specific dye. Furthermore, the dye composition of the present disclosure may contain a copolymer of the specific dye and a polymerizable compound that is a compound different from the specific dye. By including a polymerizable compound or copolymer, the dye composition of the present disclosure exhibits excellent shielding properties in at least the wavelength range of 350 nm to 450 nm, as well as excellent lightfastness and solvent resistance, due to the interaction between the polymerizable group of the specific dye and the polymerizable group of the polymerizable compound. The dye composition may also contain a polymer in which specific dyes are polymerized. Furthermore, when a polymerizable compound is included, the dye composition of the present disclosure can also be considered a polymerizable composition. These copolymers or polymers can be used as dye polymers.

[0092] As the polymerizable compound, any compound that can be polymerized and cured by applying energy can be used without limitation. Examples of the polymerizable compound include compounds having a polymerizable group with an ethylenically unsaturated bond. Examples of the polymerizable group with an ethylenically unsaturated bond include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, and a vinylphenyl group.

[0093] The polymerizable compound may be any of a monomer, a prepolymer (i.e., a dimer, trimer, or oligomer), a mixture thereof, and a (co)polymer of a compound selected from a monomer and a prepolymer. Examples of the monomer and its (co)polymer include unsaturated carboxylic acids (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), their esters, amides, and (co)polymers of the aforementioned components. Preferred polymerizable compounds are (meth)acrylate-based monomers and styrene-based monomers.

[0094] Specific examples of (meth)acrylate monomers include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, glycidyl (meth)acrylate, benzyl (meth)acrylate, 2-(2-phenoxy)ethyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, n-nonyl (meth)acrylate, isononyl (meth)acrylate, n-decyl (meth)acrylate, and isopropyl (meth)acrylate. Decyl (meth)acrylate, n-dodecyl (meth)acrylate, n-tridecyl (meth)acrylate, n-tetradecyl (meth)acrylate, n-hexadecyl (meth)acrylate, stearyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, 1-hydroxyheptyl (meth)acrylate, 1-hydroxybutyl (meth)acrylate, 1-hydroxypentyl, 2-hydroxy dibutyl (meth)acrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, ethoxylated bisphenol A diacrylate, ethoxylated bisphenol A dimethacrylate, ethoxylated trimethylolpropane triacrylate, ethoxylated trimethylolpropane trimethacrylate, ethoxylated glycerin triacrylate, ethoxylated glycerin trimethacrylate, ethoxylated pentaerythritol tetraacrylate, Ethoxylated pentaerythritol tetramethacrylate, ethoxylated dipentaerythritol hexaacrylate, polyglycerin monoethylene oxide polyacrylate, polyglycerin polyethylene glycol polyacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, trimethylolpropane triacrylate,Examples of the copolymer include trimethylolpropane trimethacrylate, tricyclodecane dimethanol diacrylate, tricyclodecane dimethanol dimethacrylate, 1,6-hexanediol diacrylate, and 1,6-hexanediol dimethacrylate.

[0095] Specific examples of styrene-based monomers include styrene, methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, fluorostyrene, chlorostyrene, methoxystyrene, t-butoxystyrene, and divinylbenzene.

[0096] As the polymerizable compound, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, benzyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dipentaerythritol hexaacrylate, and pentaerythritol triacrylate are particularly preferred because they are liquid at room temperature.

[0097] Details of the method of using the polymerizable compound, such as the structure of the polymerizable compound, whether it is used alone or in combination of two or more types, the content of the polymerizable compound, and the like, can be arbitrarily set in accordance with the final performance design of the dye composition. For example, from the viewpoint of sensitivity, a compound having a structure with a large number of polymerizable groups per molecule is preferred, and in many cases, a bifunctional or higher functional compound is preferred. Furthermore, from the viewpoint of increasing the strength of the polymer, a trifunctional or higher functional compound, for example, a hexafunctional (meth)acrylate monomer, can be used. Furthermore, compounds having different functionalities or different polymerizable groups, such as a (meth)acrylate compound, a styrene compound, a vinyl ether compound, and the like, may be used in combination.

[0098] The content of the polymerizable compound in the total solid content of the dye composition is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more. The upper limit is less than 100% by mass, and can be 99.9% by mass or less, or can be 99.5% by mass or less. Furthermore, the total content of the compound represented by Formula 1 above and, for example, the light-absorbing compound and polymerizable compound described below in the total solid content of the dye composition is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more. The upper limit can be 100% by mass, or can be 99.9% by mass or less, or can be 99.5% by mass or less. The dye composition may contain one type of polymerizable compound or two or more types. When two or more types of polymerizable compounds are contained, it is preferable that the total amount of the two or more polymerizable compounds is within the above range.

[0099] (Polymerization initiator) The dye composition of the present disclosure may contain a polymerization initiator. When the dye composition further contains a polymerization initiator, the polymerization reaction of the dye, polymerizable compound, etc. can be initiated satisfactorily. As the polymerization initiator, a compound capable of generating an initiating species necessary for the polymerization reaction upon application of energy can be used. The polymerization initiator can be appropriately selected from, for example, a photopolymerization initiator and a thermal polymerization initiator. As the polymerization initiator, a photopolymerization initiator is preferred. When a photopolymerization initiator is contained, the dye composition of the present disclosure can also be said to be a photopolymerizable composition. When a specific photopolymerization initiator is selected from among photopolymerization initiators, a dye composition can be produced in which the amount of photopolymerization initiator added is reduced by blending a specific dye, an ultraviolet absorber, etc. so that the specific photopolymerization initiator transmits light in the wavelength region in which the specific photopolymerization initiator generates free radicals.

[0100] The photopolymerization initiator is preferably, for example, a compound that absorbs light in the ultraviolet to visible region (e.g., 280 nm to 400 nm). Examples of such compounds include photoradical initiators that generate active radicals to initiate photoradical polymerization, and cationic initiators that initiate photocationic polymerization.

[0101] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives such as photopolymerization initiators having a triazine skeleton and photopolymerization initiators having an oxadiazole skeleton; acylphosphine compounds such as acylphosphine oxide; hexaarylbiimidazole; oxime compounds such as oxime derivatives; organic peroxides; thio compounds; ketone compounds; aromatic onium salts; ketoxime ethers; aminoacetophenone compounds; hydroxyacetophenone; and the like. Examples of the aminoacetophenone initiator include initiators having an absorption wavelength of 365 nm or 405 nm as described in JP-A-2009-191179 and initiators as described in JP-A-10-291969. Examples of the aminoacetophenone initiator include acylphosphine oxide initiators as described in JP-A-4225898.

[0102] The photopolymerization initiator may be a synthetic product or a commercially available product. Examples of commercially available photopolymerization initiators include hydroxyacetophenone initiators such as IRGACURE (registered trademark) 184, DAROCUR (registered trademark) 1173, IRGACURE (registered trademark) 500, IRGACURE (registered trademark) 2959, and IRGACURE (registered trademark) 127 (trade names: all manufactured by BASF Corporation); aminoacetophenone initiators such as IRGACURE (registered trademark) 907, IRGACURE (registered trademark) 369, and IRGACURE (registered trademark) 379 (trade names: all manufactured by BASF Corporation); and acylphosphine initiators such as IRGACURE (registered trademark) 819 and DAROCUR (registered trademark) TPO (trade names: all manufactured by BASF Corporation).

[0103] As the photopolymerization initiator, an oxime-based compound or an aminoacetophenone compound is preferred. Specific examples of the oxime-based compound include the compounds described in JP-A-2001-233842, JP-A-2000-80068, JP-A-2006-342166, and JP-A-2016-6475, paragraphs 0073 to 0075. Among the oxime-based compounds, the photopolymerization initiator is preferably an oxime ester-based compound, and examples of commercially available products include IRGACURE-OXE01 and IRGACURE-OXE02 (both manufactured by BASF).

[0104] Examples of the cationic polymerization initiator include initiators that initiate photocationic polymerization, photobleaching agents for dye compounds, photodiscoloring agents, known acid generators used in microresists, etc., and mixtures thereof. Specific examples of the cationic polymerization initiator include onium compounds, organic halogen compounds, and disulfone compounds.

[0105] Examples of the onium compound include diazonium salts, ammonium salts, iminium salts, phosphonium salts, iodonium salts, sulfonium salts, arsonium salts, and selenonium salts. Examples of the onium compound include the compounds described in paragraphs 0058 to 0059 of JP-A No. 2002-29162.

[0106] When the dye composition of the present disclosure contains a polymerization initiator, the dye composition may contain one type of polymerization initiator alone or two or more types. When the dye composition of the present disclosure contains a polymerization initiator, the content of the polymerization initiator in the dye composition is preferably 0.1% by mass to 20% by mass, more preferably 0.3% by mass to 15% by mass, and still more preferably 0.4% by mass to 10% by mass, relative to the total solid content of the dye composition.

[0107] The dye composition of the present disclosure can be prepared by mixing a specific dye and a solvent, and, if necessary, a polymerizable compound, a polymerization initiator, an ultraviolet absorber, and other components.

[0108] (Resin) The dye composition of the present disclosure may contain at least one resin. The resin can be appropriately selected from resins that satisfy various physical properties such as transparency, refractive index, and processability required depending on the application or purpose.

[0109] The resin may be a thermoplastic resin or a thermosetting resin. Examples of the resin include (meth)acrylic resin, epoxy resin, ene-thiol resin, carbonate resin, ether resin, arylate resin, sulfone resin, ether sulfone resin, phenylene resin, arylene ether phosphine oxide resin, imide resin, amide-imide resin, olefin resin, cyclic olefin resin, ester resin, styrene resin, urethane resin, cellulose acylate resin, and episulfide resin.

[0110] Examples of (meth)acrylic resins include polymers containing structural units derived from (meth)acrylic acid and / or its esters, specifically polymers obtained by polymerizing at least one compound selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid esters, (meth)acrylamide, and (meth)acrylonitrile.

[0111] Examples of ester resins include polymers obtained by reacting a polyol (e.g., ethylene glycol, propylene glycol, glycerin, trimethylolpropane) with a polybasic acid (e.g., aromatic dicarboxylic acids (e.g., terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, etc., and dicarboxylic acids in which hydrogen atoms on the aromatic rings of these dicarboxylic acids are substituted with methyl groups, ethyl groups, phenyl groups, etc.), aliphatic dicarboxylic acids having 2 to 20 carbon atoms (e.g., adipic acid, sebacic acid, dodecanedicarboxylic acid), or alicyclic dicarboxylic acids (e.g., cyclohexanedicarboxylic acid)), as well as polymers obtained by ring-opening polymerization of cyclic ester compounds such as caprolactone monomers (e.g., polycaprolactone).

[0112] Examples of epoxy resins include bisphenol A epoxy resins, bisphenol F epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, aliphatic epoxy resins, etc. Commercially available epoxy resins may be used, and examples of commercially available products include the following:

[0113] Examples of bisphenol A type epoxy resins include jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, and jER1010 (all manufactured by Mitsubishi Chemical Corporation), and EPICLON860, EPICLON1050, EPICLON1051, and EPICLON1055 (all manufactured by DIC Corporation). Examples of bisphenol F type epoxy resins include jER806, jER807, jER4004, jER4005, jER4007, and jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON830 and EPICLON835 (all manufactured by DIC Corporation), and LCE-21 and RE-602S (all manufactured by Nippon Kayaku Co., Ltd.). Examples of phenol novolac type epoxy resins include jER152, jER154, jER157S70, and jER157S65 (all manufactured by Mitsubishi Chemical Corporation), EPICLON N-740, EPICLON N-770, and EPICLON N-775 (all manufactured by DIC Corporation). Examples of cresol novolac epoxy resins include EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, and EPICLON N-695 (all manufactured by DIC Corporation), and EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.).Examples of aliphatic epoxy resins include the ADEKA RESIN EP series (e.g., EP-4080S, EP-4085S, and EP-4088S, manufactured by ADEKA Corporation), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (all manufactured by Daicel Corporation), DENACOL EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (all manufactured by Nagase ChemteX Corporation), and ADEKA RESIN Examples of epoxy resins include the EP series (e.g., EP-4000S, EP-4003S, EP-4010S, EP-4011S, etc.; manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, EPPN-502 (all manufactured by ADEKA Corporation), and jER1031S (manufactured by Mitsubishi Chemical Corporation). Examples of epoxy resins include Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (manufactured by NOF Corporation, epoxy group-containing polymers).

[0114] The resin may have an acid group. Examples of the acid group include a carboxyl group, a phosphoric acid group, a sulfonic acid group, and a phenolic hydroxy group. The acid group may be of one type or of two or more types. The resin having an acid group can be used as an alkali-soluble resin and can also be used as a dispersant.

[0115] The resin having an acid group is preferably a polymer having a carboxyl group in a side chain. Examples of the resin having an acid group include alkali-soluble phenolic resins such as methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, partially esterified maleic acid copolymers, novolac resins, acidic cellulose derivatives having a carboxyl group in a side chain, and resins obtained by adding an acid anhydride to a polymer having a hydroxyl group.

[0116] Among resins having an acid group, copolymers of (meth)acrylic acid and other monomers copolymerizable with (meth)acrylic acid are particularly suitable as alkali-soluble resins. Examples of other monomers copolymerizable with (meth)acrylic acid include alkyl (meth)acrylates, aryl (meth)acrylates, and vinyl compounds. Examples of alkyl (meth)acrylates and aryl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, tolyl (meth)acrylate, naphthyl (meth)acrylate, and cyclohexyl (meth)acrylate. Furthermore, as the other monomer, N-substituted maleimide monomers (e.g., N-phenylmaleimide, N-cyclohexylmaleimide, etc.) described in JP-A-10-300922 can be used. Examples of vinyl compounds include styrene, α-methylstyrene, vinyltoluene, glycidyl methacrylate, acrylonitrile, vinyl acetate, N-vinylpyrrolidone, tetrahydrofurfuryl methacrylate, polystyrene macromonomer, polymethyl methacrylate macromonomer, etc. The other monomer copolymerizable with (meth)acrylic acid may be one type or two or more types.

[0117] Examples of the resin having an acid group include a benzyl (meth)acrylate / (meth)acrylic acid copolymer, a benzyl (meth)acrylate / (meth)acrylic acid / 2-hydroxyethyl (meth)acrylate copolymer, a benzyl (meth)acrylate / (meth)acrylic acid / other monomer copolymer, and a polymer of 2-hydroxyethyl (meth)acrylate; and the 2-hydroxypropyl (meth)acrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer, 2-hydroxy-3-phenoxypropyl acrylate / polymethyl methacrylate macromonomer / benzyl methacrylate / methacrylic acid copolymer, 2-hydroxyethyl methacrylate / polystyrene macromonomer / methyl methacrylate / methacrylic acid copolymer, and 2-hydroxyethyl methacrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymer described in JP-A-7-140654.

[0118] For examples of resins having acid groups, see paragraphs

[0558] to

[0571] of JP 2012-208494 A (corresponding to paragraphs

[0685] to

[0700] of U.S. Patent Application Publication No. 2012 / 0235099 A) and paragraphs

[0076] to

[0099] of JP 2012-198408 A, the contents of which are incorporated herein by reference. Furthermore, Acribase FF-426 (manufactured by Nippon Shokubai Co., Ltd.) can also be used as a resin having acid groups.

[0119] The acid value of the resin having an acid group is preferably 30 mgKOH / g to 200 mgKOH / g. The lower limit of the acid value is preferably 50 mgKOH / g or more, more preferably 70 mgKOH / g or more. The upper limit of the acid value is preferably 150 mgKOH / g or less, more preferably 120 mgKOH / g or less. The acid value of the resin is measured in accordance with JIS K0070 (1992) and calculated by converting 1 mmol / g = 56.1 mgKOH / g.

[0120] The resin may have a polymerizable group. The resin is preferably a copolymer containing a structural unit having a polymerizable group. Examples of the polymerizable group include a group having an ethylenically unsaturated bond, an epoxy group, a methylol group, and an alkoxysilyl group. Examples of the group having an ethylenically unsaturated bond include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group. Examples of the alkoxysilyl group include a monoalkoxysilyl group, a dialkoxysilyl group, and a trialkoxysilyl group.

[0121] Examples of the structural unit having a polymerizable group include those represented by the following formulae (A2-1) to (A2-4).

[0122]

[0123] X １ represents a hydrogen atom or an alkyl group. １ The number of carbon atoms in the alkyl group in X is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. １ is preferably a hydrogen atom or a methyl group.

[0124] L ５１ represents a single bond or a divalent linking group. ５１ Examples of the divalent linking group in the formula (I) include an alkylene group, an arylene group, —O—, —S—, —CO—, —COO—, —OCO—, and —SO ２ Examples of the divalent linking group include -, -NR- (wherein R represents a hydrogen atom or an alkyl group, preferably a hydrogen atom), and a group combining two or more of these. As the divalent linking group, a group combining at least one selected from an alkylene group and an arylene group with -O- is preferred. ５１ The number of carbon atoms in the alkylene group in the formula is preferably 1 to 30, more preferably 1 to 15, and even more preferably 1 to 10. The alkylene group may be unsubstituted or may have a substituent, and is preferably unsubstituted. The alkylene group may be linear, branched, or cyclic. Furthermore, the cyclic alkylene group may be either monocyclic or polycyclic. L ５１ The arylene group in the formula (I) preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0125] Y １ represents a polymerizable group. Examples of the polymerizable group include a group having an ethylenically unsaturated bond, an epoxy group, a methylol group, and an alkoxysilyl group. Details of the group having an ethylenically unsaturated bond, an epoxy group, a methylol group, and an alkoxysilyl group are as described above.

[0126] Commercially available resins containing polymerizable groups may be used. Examples of commercially available products include the Dianal BR series (polymethyl methacrylate (PMMA), for example, Dianal BR-80, BR-83, and BR-87; Mitsubishi Chemical Corporation); Photomer 6173 (a COOH-containing polyurethane acrylic oligomer, Diamond Shamrock Co., Ltd.); Viscoat R-264 and KS Resist 106 (both manufactured by Osaka Organic Chemical Industry Ltd.); Cyclomer P series (for example, ACA230AA) and Plaxel CF200 series (both manufactured by Daicel Corporation); Ebecryl 3800 (Daicel-UCB Corporation); and AcriCure RD-F8 (Nippon Shokubai Co., Ltd.). Other examples include the products described above for epoxy resins.

[0127] When a dye composition containing a resin is used, for example, in applications such as lenses (e.g., eyeglass lenses), the resin is preferably a thermoplastic resin such as a carbonate resin or a (meth)acrylic resin (e.g., polymethyl methacrylate (PMMA)), or a thermosetting resin such as a urethane resin. Examples of commercially available carbonate resins include polycarbonate resin composition (Caliber 200-13: product name, Sumitomo Dow Co., Ltd.) and diethylene glycol bisallyl carbonate resin (CR-39: product name, PPG Industries). The urethane resin is preferably a thiourethane resin. Examples of commercially available raw materials for thiourethane resins include thiourethane resin monomers (MR-7, MR-8, MR-10, MR-174: product names, Mitsui Chemicals, Inc.).

[0128] The weight average molecular weight (Mw) of the resin is preferably 2,000 to 2,000,000. The lower limit of Mw is preferably 5,000 or more, more preferably 10,000 or more, and more preferably 50,000 or more. The upper limit of Mw is preferably 1,000,000 or less, more preferably 500,000 or less, and even more preferably 200,000 or less. Furthermore, when an epoxy resin is used, the weight average molecular weight of the epoxy resin is preferably 100 or more, more preferably 200 to 2,000,000. The upper limit of Mw of the epoxy resin is preferably 1,000,000 or less, and more preferably 500,000 or less. The lower limit of Mw of the epoxy resin is preferably 2,000 or more.

[0129] The weight average molecular weight (Mw) is a value measured by gel permeation chromatography (GPC). Measurement by GPC is performed using an HLC (registered trademark)-8020GPC (Tosoh Corporation) as a measuring device, three TSKgel (registered trademark) Super Multipore HZ-H columns (4.6 mm ID (inner diameter) × 15 cm (length), Tosoh Corporation), and THF (tetrahydrofuran) as an eluent. The measurement conditions are a sample concentration of 0.45% by mass, a flow rate of 0.35 ml / min, a sample injection amount of 10 μl, and a measurement temperature of 40°C, and the measurement is performed using an RI detector. The calibration curve is prepared from eight samples of "Standard Sample TSK Standard, Polystyrene" from Tosoh Corporation: "F-40", "F-20", "F-4", "F-1", "A-5000", "A-2500", "A-1000", and "n-propylbenzene".

[0130] The resin may be contained alone or in combination of two or more. The content of the resin in the resin composition is preferably 70% by mass to 99.9% by mass, more preferably 80% by mass to 99.9% by mass, based on the total solid content of the resin composition. When the content of the resin in the resin composition is within the above range, good moldability is achieved during molding.

[0131] (Light-Absorbing Compound) The dye composition of the present disclosure may contain a light-absorbing compound as needed. Light-absorbing compounds include not only compounds that absorb visible light, but also compounds that absorb ultraviolet light and near-infrared light. By including a light-absorbing compound in the dye composition, it is possible to provide a dye composition in which the wavelength range of transmitted light is controlled in various ways depending on the wavelength range of light absorbed by the dye contained in the dye composition and the wavelength range of light absorbed by the light-absorbing compound. For example, by including an ultraviolet absorber as the light-absorbing compound in the dye composition, the effect of blocking or suppressing ultraviolet light in addition to blue light is further enhanced. Furthermore, it is possible to provide a dye composition that transmits only violet light. Furthermore, it is possible to provide a dye composition that blocks both blue light and infrared light.

[0132] The dye composition preferably contains a light-absorbing compound having a maximum absorption wavelength on the shorter wavelength side than the specific dye. Such light-absorbing compounds include various ultraviolet absorbers. Various ultraviolet absorbers can be selected depending on the application, such as an ultraviolet absorber that absorbs UV-B in the wavelength range of 280 nm to 320 nm, an ultraviolet absorber that absorbs UV-A in the wavelength range of 320 nm to 400 nm, or an ultraviolet absorber that absorbs UV-C in some cases at 280 nm or less.

[0133] For example, in order to obtain a dye composition that can shield light having wavelengths in the ultraviolet region over a wide range, the difference between the maximum absorption wavelength of the specific dye and the maximum absorption wavelength of the ultraviolet absorber is preferably 0 to 70 nm, more preferably 20 to 60 nm, and even more preferably 30 to 50 nm.

[0134] Examples of the ultraviolet absorber include ultraviolet absorbing compounds selected from the group consisting of aminobutadiene compounds, benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, dibenzoylmethane compounds, cinnamic acid compounds, acrylate compounds, benzoic acid ester compounds, oxalic acid diamide compounds, formamidine compounds, benzoxazinone compounds, benzoxazole compounds, and benzodithiol compounds. Ultraviolet absorbers that can be used in the present embodiment are described, for example, in Fine Chemical, May 2004 issue, pp. 28 to 38; "New Developments in Functional Additives for Polymers" (Toray Research Center, 1999) published by the Research and Development Division of Toray Research Center, pp. 96 to 140; "Development of Polymer Additives and Environmental Measures" edited by Yasukazu Ohkatsu (CMC Publishing, 2003) pp. 54 to 64; and "Mechanisms of Polymer Degradation and Discoloration and Their Stabilization Techniques - Collection of Know-How" (Technical Information Association, 2006) published by Technical Information Association Inc., and can also be appropriately selected from the compounds described in the above-mentioned documents depending on the purpose.

[0135] Examples of ultraviolet absorbers include the compounds shown below. Benzoxazole compounds include, for example, the compound represented by general formula (II) described as a fluorescent brightening agent in Japanese Patent No. 4,311,869. Benzoxazinone compounds include, for example, the compounds described in Japanese Patent Nos. 5,591,453 and 5,250,289. Merocyanine compounds include, for example, the compounds described in JP-A-2011-184414. Benzodithiol compounds include, for example, the compounds described in Japanese Patent Nos. 5,450,994 and 5,364,311. Specific examples of benzoxazinone compounds include UV-1 to UV-3 having the following structures:

[0136]

[0137] Examples of merocyanine compounds include UV-4 and UV-5 having the following structures:

[0138]

[0139] Examples of benzoxazole compounds include UV-6 and UV-7 having the following structure:

[0140]

[0141] Examples of benzodithiol compounds include UV-8 and UV-9 having the following structure.

[0142]

[0143] The ultraviolet absorber is preferably a 2-(2-hydroxyphenyl)benzotriazole-based compound, a 2-(2-hydroxyphenyl)-1,3,5-triazine-based compound, or a 2-hydroxybenzophenone-based compound, from the viewpoint of having a short absorption wavelength and relatively high light resistance.

[0144] The light-absorbing compound is also preferably a compound having a polymerizable group. According to this embodiment, by interacting with the polymerizable group of the dye, it is possible to control the absorption wavelength range and form a dye composition having excellent lightfastness and solvent resistance. Examples of the polymerizable group include the polymerizable groups having an ethylenically unsaturated bond described in the section on specific dyes, and are preferably a (meth)acryloyloxy group, a (meth)acryloylamino group, a (meth)allyl group, or a vinylphenyl group. Examples of commercially available ultraviolet absorbers having a polymerizable group include 2-[2-hydroxy-5-(2-methacryloyloxyethyl)phenyl]2H-benzo[d][1,2,3]triazole (RUVA-93, manufactured by Otsuka Chemical Co., Ltd.).

[0145] When the dye composition contains a light-absorbing compound, the light-absorbing compound may be contained alone or in combination of two or more types. The content of the light-absorbing compound may be appropriately selected depending on the type of light-absorbing compound, and generally can be 0.01% to 20% by mass relative to the total mass of the dye composition. The content of the light-absorbing compound in the total solid content of the dye composition is preferably 0.01% to 10% by mass, more preferably 0.01% to 5% by mass. The total content of the dye and the light-absorbing compound in the total solid content of the dye composition is preferably 0.01% to 20% by mass, more preferably 0.01% to 10% by mass. The content of the light-absorbing compound is preferably 1 part to 400 parts by mass, more preferably 10 parts to 200 parts by mass, relative to 100 parts by mass of the dye.

[0146] (Other Dyes) The dye composition of the present disclosure may contain other dyes different from the specific dye, as needed depending on the application or purpose. The other dyes include dyes that absorb specific wavelengths, such as ultraviolet absorbers, infrared absorbers, and blue light absorbers. The dyes include dyes, pigments, and the like. Examples of the other dyes include phthalocyanine dyes, xanthene dyes, triarylmethane dyes, methine dyes, azo dyes, and anthraquinone dyes, all of which are described as phthalocyanine compounds in U.S. Patent Publication No. 2008 / 0076044 A1, as well as dipyrromethene dyes described in JP-A-2008-292970. The other dyes may or may not have a maximum absorption wavelength in the wavelength range of 450 nm to 500 nm.

[0147] As the dye that is the other coloring matter, from the viewpoint of better exhibiting the ultraviolet ray and blue light blocking and suppressing functions, phthalocyanine dyes, xanthene dyes, triarylmethane dyes, methine dyes, azo dyes, anthraquinone dyes, dipyrromethene dyes, and the like are preferred.

[0148] Examples of pigments that are other coloring matters include perylene, perinone, quinacridone, quinacridonequinone, anthraquinone, anthanthrone, benzimidazolone, disazo condensation, disazo, azo, indanthrone, phthalocyanine, triarylcarbonium, dioxazine, aminoanthraquinone, diketopyrrolopyrrole, indigo, thioindigo, isoindoline, isoindolinone, pyranthrone, and isoviolanthrone.

[0149] When the dye composition of the present disclosure contains a pigment different from the specific dye, from the viewpoint of visibility when applied to optical materials, the average primary particle diameter of the pigment is preferably 200 nm or less, more preferably 10 nm to 200 nm, and even more preferably 10 nm to 100 nm. When a pigment is contained in the dye composition of the present disclosure, it is preferable to previously mix the pigment with a dispersant, an organic solvent, etc. to prepare a pigment dispersion in which the pigment is dispersed, and then mix the pigment with other components to contain it in the dye composition.

[0150] (Solvent) The dye composition of the present disclosure may contain at least one solvent. When the dye composition of the present disclosure contains a solvent, it is a liquid composition. Examples of the solvent include water, an organic solvent, and a mixed solvent of water and an organic solvent.

[0151] The water that can be used may be distilled water, ion-exchanged water, etc. The organic solvent may be appropriately selected depending on the use or purpose of the dye composition, and examples thereof include esters, ethers, ketones, aromatic hydrocarbons, etc.

[0152] Examples of esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkyl oxyacetate solvents (e.g., methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (specifically, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.)), alkyl 3-oxypropionate solvents (e.g., methyl 3-oxypropionate, ethyl 3-oxypropionate (specifically, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc.)), and alkyl 2-oxypropionate solvents (e.g., 2-oxypropionate). Examples of suitable solvents include methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate (specifically, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, and ethyl 2-ethoxypropionate), 2-oxy-2-methylpropionic acid alkyl ester solvents (methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate (specifically, methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate)), methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, cyclohexyl acetate, and 1-methyl-2-methoxyethyl propionate.

[0153] Examples of ethers include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (also referred to as PEGMEA), diethylene glycol monoethyl ether acetate (also referred to as ethyl carbitol acetate), diethylene glycol monobutyl ether acetate (also referred to as butyl carbitol acetate), propylene glycol monoethyl ether acetate, and propylene glycol monopropyl ether acetate.

[0154] Examples of ketones include methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone.

[0155] Suitable examples of aromatic hydrocarbons include toluene and xylene.

[0156] The organic solvent may be used alone in the dye composition, or two or more may be used in combination from the viewpoint of the intended use, the solubility of each component, improvement of the coated surface state, etc. When two or more organic solvents are used in combination, it is preferable that the organic solvents include two or more selected from the group consisting of methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate.

[0157] The content of the solvent in the dye composition is preferably an amount such that the total solid content in the dye composition is 10% by mass to 80% by mass, more preferably 15% by mass to 60% by mass.

[0158] (Other Components) The dye composition of the present disclosure may contain components other than the above-described components. Examples of the other components include a filler, a surfactant, a polymerizable compound, a polymerization initiator, an adhesion promoter, an antioxidant, an anti-aggregation agent, etc.

[0159] <Compound> The compound of the present disclosure is a compound represented by the following formula 1. The compound represented by formula 1 is a novel compound.

[0160]

[0161] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of the groups is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0162] The compound represented by Formula 1 is the compound described above as the specific dye. Therefore, the description of the compound represented by Formula 1 is the same as the description of the specific dye described above. Therefore, the description of the compound represented by Formula 1 will be omitted here. The compound of the present disclosure is a dye having a polymerizable group, and can be suitably used as a monomer such as a dye monomer or a coloring monomer. The compound of the present disclosure has high absorbance to blue light and excellent light resistance and solvent resistance, and therefore, even in a dye monomer, etc., it can be made into a dye monomer, etc. that has high absorbance to blue light and excellent light resistance and solvent resistance, and can suppress diffusion, bleed-out, phase separation, precipitation, etc. of the dye.

[0163] <Dye> The dye of the present disclosure is a dye represented by the following formula 1. The dye represented by the following formula 1 is the compound described above as the specific dye. Since the compound described above as the specific dye is a novel compound, the dye of the present disclosure is also a novel dye.

[0164]

[0165] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of the groups is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0166] The description of the dye of the present disclosure is the same as the description of the specific dye described above. Therefore, a description of the dye of the present disclosure will be omitted here. The dye of the present disclosure is a dye having a polymerizable group and can be suitably used as a monomer for dye monomers, coloring monomers, etc. The dye of the present disclosure has high absorbance to blue light and excellent light fastness and solvent resistance, and therefore can be used as a dye monomer or the like to have high absorbance to blue light and excellent light fastness and solvent resistance, and can suppress diffusion, bleed-out, phase separation, precipitation, etc. of the dye.

[0167] <Blue Color Filtering Agent> The blue color filtering agent of the present disclosure is a blue color filtering agent represented by the following formula 1. The blue color filtering agent represented by the following formula 1 is the compound explained above as the specific dye. Since the compound explained above as the specific dye is a novel compound, the blue color filtering agent of the present disclosure is also a novel blue color filtering agent.

[0168]

[0169] In formula 1, R １and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. ５ and R ６ may be bonded to each other to form a 6-membered ring. １ ~R ６ At least one of the groups is a group containing a polymerizable group having an ethylenically unsaturated bond.

[0170] The explanation of the blue screening agent represented by Formula 1 is the same as the explanation of the specific dye described above. Therefore, here, the explanation of the blue screening agent represented by Formula 1 will be omitted. The blue screening agent of the present disclosure is a dye having a polymerizable group, and can be suitably used as a monomer such as a dye monomer or a coloring monomer. The blue screening agent of the present disclosure has high absorbance to blue light and excellent light fastness and solvent resistance, and therefore, even in the case of a dye monomer or the like, it can be made into a blue screening agent having high absorbance to blue light and excellent light fastness and solvent resistance, and can suppress diffusion, bleed-out, phase separation, precipitation, etc. of the dye.

[0171] <Polymer> The polymer of the present disclosure is a polymer (hereinafter also referred to as polymer (1)) containing a structural unit derived from the compound of the present disclosure represented by the above formula 1. The polymer (1) can be obtained by subjecting the compound of the present disclosure to a polymerization reaction. As described above, in the compound of the present disclosure, R １ ~R ６ At least one of R is a group containing a polymerizable group having an ethylenically unsaturated bond. Depending on the position and number of the group containing a polymerizable group having an ethylenically unsaturated bond in the compound of the present disclosure, the structural units derived from the compound of the present disclosure contained in the polymer (1) vary. In one preferred embodiment, R ４ is a group containing a polymerizable group having an ethylenically unsaturated bond. In this case, the structural unit derived from the compound of the present disclosure is represented by the following formula 5, for example.

[0172]

[0173] In formula 5, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ５ and R ６ R each independently represents a hydrogen atom, an alkyl group, or an aryl group. ５ and R ６ may be bonded to each other to form a 6-membered ring. Q is a residue of a group containing a polymerizable group having an ethylenically unsaturated bond. １ ~R ６ is R in Equation 1 １ ~R ６ The same applies to the group containing a polymerizable group having an ethylenically unsaturated bond as the "group containing a polymerizable group having an ethylenically unsaturated bond" in Formula 1.

[0174] Since polymer (1) contains a structure derived from the compound of the present disclosure, it may be a polymer formed by polymerizing compounds of the present disclosure together. Furthermore, polymer (1) can be obtained using a dye composition containing the compound of the present disclosure as a dye. Therefore, polymer (1) may contain, depending on the components contained in the dye composition, for example, a polymerizable compound different from the compound of the present disclosure, a resin, another dye, a light-absorbing compound, an ultraviolet absorber, etc., and may also contain a structure derived from compound (1). Polymer (1) may form a copolymer of compound (1) and a polymerizable compound. Furthermore, when a compound having a polymerizable group is used as the ultraviolet absorber, polymer (1) may form a copolymer of compound (1) and the ultraviolet absorber. In this case, when a polymerizable compound is further contained, polymer (1) may form a copolymer of compound (1), the ultraviolet absorber, and the polymerizable compound.

[0175] The content of the structure derived from the compound represented by Formula 1 in Polymer (1) is preferably 0.01% by mass to 100% by mass. The upper limit is more preferably 50% by mass or less, and even more preferably 20% by mass or less. The lower limit is more preferably 0.02% by mass or more, and even more preferably 0.1% by mass or more. The content of the structure derived from the polymerizable compound described above in Polymer (1) is preferably 50% by mass to 99.99% by mass. The upper limit is more preferably 99.99% by mass or less, and even more preferably 99.9% by mass or less. The lower limit is more preferably 50% by mass or more, and even more preferably 90% by mass or more. The content of the structure derived from the ultraviolet absorber other than the structure represented by Formula 5 in Polymer (1) is preferably 0.01% by mass to 90% by mass. The upper limit is more preferably 50% by mass or less, and even more preferably 10% by mass or less. The lower limit is more preferably 0.02% by mass or more, and even more preferably 0.1% by mass or more. The weight average molecular weight of polymer (1) is preferably 5,000 to 80,000, more preferably 10,000 to 60,000, and even more preferably 10,000 to 40,000.

[0176] Polymer (1) is a polymer containing a structural unit derived from the compound of the present disclosure represented by Formula 1, and can be preferably used, for example, as a dye polymer, a colored polymer, a copolymer polymer, etc. Polymer (1) of the present disclosure has high absorbance to blue light and excellent light resistance and solvent resistance, and therefore, even in the case of a dye polymer, etc., it can be made into a dye polymer having high absorbance to blue light and excellent light resistance and solvent resistance, and can suppress diffusion, bleed-out, phase separation, precipitation, etc. of the dye.

[0177] <Cured Product> The cured product of the present disclosure is obtained from the dye composition of the present disclosure. Specifically, the cured product of the present disclosure is obtained by curing the dye composition of the present disclosure. The curing method may be any method that hardens the dye composition of the present disclosure, such as a method of drying to solidify or a method of hardening by a curing reaction. The cured product may be obtained as a molded product obtained by molding the dye composition of the present disclosure into a desired shape. The shape of the molded product can be appropriately selected depending on the application and purpose. Examples include a coating film, a film, a sheet, a plate, a lens, a tube, and a fiber.

[0178] The cured product is preferably used as an optical component. Examples of optical components include ultraviolet cut filters, lenses, and protective materials. The cured product can also be used in polarizing plates and the like. The ultraviolet cut filters can be used in products such as optical filters, display devices, solar cells, and window glass. The type of display device is not particularly limited, and examples include liquid crystal display devices and organic electroluminescence display devices. When the cured product is used as a lens, the cured product of the present disclosure may be formed into a lens shape. The cured product of the present disclosure may also be used as a coating film on the lens surface or as an intermediate layer (adhesive layer) of a cemented lens. The type of protective material is not particularly limited, and examples include protective materials for display devices, protective materials for solar cells, protective materials for window glass, and organic electroluminescence display devices. The shape of the protective material is not particularly limited, and examples include coating film, film, and sheet shapes.

[0179] The cured product of the present disclosure can be a cured product with a controlled wavelength range of transmitted light. Because the cured product of the present disclosure contains the specific dye or the like described above, it absorbs light in a wavelength range of 380 nm to 450 nm. Therefore, by incorporating a UV absorber that absorbs light in a specific wavelength range, depending on the application, purpose, etc., it is possible to provide a cured product with a controlled wavelength range of transmitted light. Examples of such a cured product include a cured product that blocks a wide range of wavelengths from UV to blue light, a cured product that transmits the wavelength range in which the photopolymerization initiator acts and blocks UV and blue light, and a cured product that transmits violet light and blocks UV and blue light.

[0180] <Optical Material> The optical material of the present disclosure includes the cured product of the present disclosure. Accordingly, the optical material of the present disclosure includes at least a specific dye. As a result, the optical material of the present disclosure has excellent shielding properties in the wavelength region of 350 nm to 450 nm, as well as excellent light resistance and solvent resistance.

[0181] In the present disclosure, the term "cured product" includes a dried product obtained by drying and solidifying a resin composition or a liquid composition, and, in the case where a resin composition or a liquid composition undergoes a curing reaction, a cured product obtained by curing the resin composition or the liquid composition.

[0182] Examples of optical materials include optical filters (e.g., optical lenses), and optical films or optical sheets (e.g., window films for vehicles or houses, display films for various image display devices (LCDs, organic EL elements, etc.) or mobile terminals (smartphones, tablets, etc.)). Optical films or optical sheets include protective films or protective sheets for imparting a protective function.

[0183] The optical material may be an optical material obtained as a molded product by molding a resin composition into a desired shape. That is, the optical material may be a molded product molded from a resin composition or a liquid composition. For example, in the case of an optical lens such as a spectacle lens, the optical material may be an optical material obtained by molding a resin composition into a lens shape.

[0184] The optical material may also be an optical material having a transparent supporting substrate and a resin layer laminated together. In this case, at least one of the supporting substrate and the resin layer is formed from a resin composition or a liquid composition. The optical material may be, for example, an optical film or optical sheet having a transparent supporting substrate and a dye-containing layer (resin layer) containing a specific dye, or a protective sheet having a transparent supporting substrate laminated with a hard coat layer and an adhesive layer or bonding layer. In the case of a protective sheet, the specific dye may be contained in at least one of the supporting substrate, the hard coat layer, and the adhesive layer or bonding layer. For example, the adhesive layer disposed on the supporting substrate may contain the specific dye, and the adhesive layer or bonding layer may have both a blocking function for ultraviolet light, blue light, etc. and an adhesive or bonding function.

[0185] The details and preferred embodiments of the dye (specific dye) and resin represented by Formula 1 contained in the optical material, as well as the components other than the specific dye and resin, are the same as those of the resin composition described above, and therefore detailed description thereof will be omitted here.

[0186] Hereinafter, one embodiment of the present disclosure will be described more specifically with reference to examples, but the present disclosure is not limited to the following examples as long as it does not deviate from the gist of the disclosure.

[0187] (Example 1): Compound Z-39

[0188] According to the above scheme, 4.0 g of indole-3-carbaldehyde, 5.7 g of potassium carbonate, and 10 ml of dimethylformamide were added, and 5.1 g of chloromethylstyrene was slowly added dropwise. Then, a small amount of di-t-butylhydroxytoluene (BHT) was added, and the mixture was heated and stirred at 90°C for 3 hours. After the reaction was completed and the mixture was allowed to cool to room temperature, 10 ml of methanol and 100 ml of water were slowly added in that order, and the resulting crystals were filtered and washed with ethanol to obtain 5.7 g of compound 1 (yield 78%).

[0189]

[0190] 1.0 g of 1,2-dibenzylpyrazolidine-3,5-dione, 0.93 g of compound 1, and 15 ml of methanol were added, and a small amount of BHT was added, followed by heating under reflux for 5 hours. After completion of the reaction, 15 ml of methanol was added, and the mixture was cooled to room temperature. The precipitated solid was filtered and washed with methanol. The obtained solid was then purified by silica gel chromatography to obtain 1.5 g of compound Z-39 (yield 79%).

[0191] The structure of compound Z-39 is １ The results confirmed by H-NMR are shown below. １ H-NMR (CDCl ３ ):δ 9.85 (s, 1H), 8.43 (s, 1H), 7.99 (d, 1H), 7.38-7.16 (m, 17H), 6.70-6.63 (m, 1H), 5.74-5.69 (m, 1H), 5.44 (s, 2H), 5.26-5.23 (m, 1H), 4.81 (s, 4H)

[0192] The obtained compound Z-39 was dissolved in ethyl acetate, and the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) were measured using a spectrophotometer UV-1800PC (Shimadzu Corporation) with a cell having an optical path length of 10 mm. As a result, the maximum absorption wavelength (λmax) of compound Z-39 was 418 nm, and the molar absorption coefficient (ε) was 39,300. The results of the maximum absorption wavelength (λmax, [nm]) and the molar absorption coefficient (ε) are also shown in Table 6 below.

[0193] (Example 2): Compound Z-44

[0194] Compound Z-44 (yield 31%) was obtained by the same reaction as in the synthesis of compound Z-39 in Example 1, except that compound 1 used was changed to compound 2.

[0195] The structure of compound Z-44 is １ The results confirmed by H-NMR are shown below. １ H-NMR (CDCl ３):δ 9.73 (s, 1H), 8.38 (s, 1H), 7.99-7.96 (m, 1H), 7.47-7.43 (m, 1H), 7.38-7.15 (m, 8H), 7.18-7.15 (m, 4H), 6.04-6.03 (m, 1H), 5.54-5.53 (m, 1H), 4.81-4.80 (m, 4H), 4.66-4.60 (m, 1H), 4.34-4.23 (m, 4H), 1.89-1.88 (m, 3H), 1.26-1.25 (m, 3H)

[0196] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound Z-44 were measured in the same manner as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 6 below.

[0197] (Example 3): Compound Z-46

[0198] Compound Z-46 (yield 42%) was obtained by the same reaction as in the synthesis of compound Z-39 in Example 1, except that compound 1 used in the synthesis of compound Z-39 was changed to compound 3.

[0199] The structure of compound Z-46 is １ The results confirmed by H-NMR are shown below. １ H-NMR (CDCl ３ ):δ 9.73 (s, 1H), 8.38 (s, 1H), 7.98-7.96 (m, 1H), 7.47-7.44 (m, 1H), 7.38-7.26 (m, 8H), 7.17-7.14 (m, 4H), 6. 04-6.03 (m, 1H), 5.54-5.53 (m, 1H), 4.81-4.80 (m, 4H), 4.66-4.60 (m, 1H), 4.39-4.23 (m, 3H), 1.88 (s, 3H)

[0200] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound Z-46 were measured in the same manner as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 6 below.

[0201] (Example 4): Compound Z-21

[0202] Compound Z-21 (yield 80%) was obtained by the same reaction as in the synthesis of compound Z-39 in Example 1, except that dibenzylpyrazolidinedione was changed to dibutylpyrazolidinedione.

[0203] The structure of compound Z-21 is １ The results confirmed by H-NMR are shown below. １ H-NMR (CDCl ３ ): δ 9.79 (s, 1H), 8.30 (s, 1H), 7.97-7.95. (m, 1H), 7.36-7.24 (m, 5H), 7.16-7.14 (m, 2H), 6.69-6.63 (m, 1H), 5.74-5.69 (m, 1H), 5.43 (s, 2H) ), 5.26-5.23 (m, 1H), 3.72-3.67 (m, 4H), 1.62-1.59 (m, 4H), 1.39-1.29 (m, 4H), 0.95-0.91 (m, 6H)

[0204] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound Z-21 were measured in the same manner as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 6 below.

[0205] (Examples 5 to 25) The other compounds listed in Tables 1 to 5 above were also synthesized in the same manner, and their maximum absorption wavelengths (λmax) and molar absorption coefficients (ε) were measured. The synthesized compounds were designated Compounds 1 to 25 as shown in Table 6, and the measurement results of the maximum absorption wavelengths (λmax) and molar absorption coefficients (ε) for each compound are shown in Table 6 below. Compounds 1 to 25 were designated Examples 1 to 25, respectively.

[0206]

[0207] (Comparative Example 1): Compound T-1

[0208] Compound T-1, which does not have a group containing a polymerizable group having an ethylenically unsaturated bond, was synthesized with reference to the examples of Patent Document 1 (WO 2020 / 235674).

[0209]

[0210] (Example 101 and Comparative Example 101): Polymerizable composition (photopolymerizable composition) and cured film (photocured film) Compounds 1 to 25 obtained in Examples 1 to 25 were used as dyes, and the following components were mixed to prepare polymerizable compositions 1 to 25, respectively. Compound T-1 obtained in Comparative Example 1 was used as dye, and the following components similar to those used in polymerizable compositions 1 to 25 were mixed to prepare polymerizable composition 26. Note that KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.) was used as the polymerizable compound, DIANAL BR-80 (manufactured by Mitsubishi Chemical Corporation) was used as the resin, Irgacure OXE01 (manufactured by BASF) was used as the photopolymerization initiator, Megafac F-781F (manufactured by Dainippon Ink and Chemicals, Inc.) was used as the surfactant, and propylene glycol monomethyl ether acetate was used as the solvent. In Table 7 below, compounds Z-1 to Z-141 are the same compounds as compounds Z-1 to Z-141 shown in Tables 1 to 5, respectively, and are compounds of the present disclosure. T-1 is the compound described in Comparative Example 1.

[0211] Dyes (Compounds 1 to 25, T-1): 0.6 parts by mass Polymerizable compound: 12.9 parts by mass Resin: 12.9 parts by mass Photopolymerization initiator: 2.5 parts by mass Surfactant: 0.04 parts by mass Solvent: 79.4 parts by mass

[0212]

[0213] Each of the produced polymerizable compositions 1 to 26 (see Table 7) was spin-coated onto a 50 mm (length) × 50 mm (width) square glass substrate (1737, Corning Incorporated) so that the film thickness after formation would be 1.0 μm, and the substrate was dried at 120°C for 5 minutes to form a resin composition layer. After formation, the resin composition layer was exposed to an i-line stepper exposure device (UX-1000SM-EH04, Ushio Inc.) at 1000 mJ / cm ２ Photocured films, which were cured products of each of the polymerizable compositions 1 to 26, were produced by exposing the entire surface to an exposure amount of 1000 ppm.

[0214] (Evaluation 1) 1. Lightfastness For the photocured films produced in Example 101 and Comparative Example 101, the absorbance retention rate at the maximum absorption wavelength (λmax, unit: nm) was determined under the following conditions and used as an index for evaluating lightfastness. Specifically, the absorbance of the photocured film at λmax was measured using a spectrophotometer (UV-1900PC, manufactured by Shimadzu Corporation), and then the photocured film was subjected to a 3-day lightfastness test under the following conditions. The absorbance of the photocured film after the lightfastness test at λmax was measured. Next, the absorbance retention rate L (%) was calculated using the absorbance values ​​at λmax of the photocured film before and after the lightfastness test according to the following equation 6, and lightfastness was evaluated according to the following evaluation criteria. A higher absorbance retention rate L indicates better lightfastness. The evaluation results are shown in the lightfastness column of Table 8. The number in parentheses in the lightfastness column is the absorbance retention rate value.

[0215] Absorbance retention rate L1 (%) = (absorbance at λmax of photocured film after light resistance test / absorbance at λmax of photocured film before light resistance test) × 100 Formula 6

[0216] -Conditions- Apparatus: Low-temperature cycle xenon weather meter (XL75, manufactured by Suga Test Instruments Co., Ltd.) Illuminance: 90 klx (40 w / m ２ ) Time: 3 days Environment: 23°C, relative humidity 50%

[0217] -Evaluation criteria- A: Absorbency maintenance rate L1 is 95% or more. B: Absorbency maintenance rate L1 is 90% or more and less than 95%. C: Absorbency maintenance rate L1 is 80% or more and less than 90%. D: Absorbency maintenance rate L1 is less than 80%.

[0218] 2. Solvent Resistance Evaluation For the photocured films produced in Example 101 and Comparative Example 101, the absorbance retention rate at the maximum absorption wavelength (λmax, units: nm) was determined under the following conditions and used as an index for evaluating solvent resistance. Specifically, the absorbance of the photocured film at λmax was measured using a spectrophotometer (UV-1900PC, manufactured by Shimadzu Corporation). The photocured film was then subjected to a solvent resistance test in which the film was immersed in PGMEA (propylene glycol monomethyl ether acetate) for 5 minutes. The absorbance of the photocured film after the solvent resistance test was then measured at λmax. The absorbance retention rate S (%) was then calculated using the absorbance values ​​at λmax of the photocured film before and after the solvent resistance test according to Equation 7 below, and solvent resistance was evaluated according to the following evaluation criteria. A higher absorbance retention rate S indicates better solvent resistance. The evaluation results are shown in the solvent resistance column of Table 8.

[0219] Absorbance retention rate S (%) = (absorbance after immersion / absorbance before immersion) × 100 Formula 7

[0220] -Evaluation criteria- A: The absorbance maintenance rate S is 95% or more. B: The absorbance maintenance rate S is 80% or more and less than 95%. C: The absorbance maintenance rate S is 75% or more and less than 80%. D: The absorbance maintenance rate S is less than 75%.

[0221]

[0222] Example 102: Cured product (photocured film) Polymerizable compositions using each of Compounds 1 to 25 as a dye were prepared in the same manner as in Example 101, except that the photopolymerization initiator in Example 101 was changed to IRGACURE OXE 02 (manufactured by BASF) or Omnirad TPO (manufactured by IGM Resins B.V.). In addition, in Example 101, each of the polymerizable compounds was changed to a mixture of one or more selected from KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.), Light Acrylate DCP-A (manufactured by Kyoeisha Chemical Co., Ltd.), KAYARAD D-330 (manufactured by Nippon Kayaku Co., Ltd.), KAYARAD D-320 (manufactured by Nippon Kayaku Co., Ltd.), and KAYARAD D-310 (manufactured by Nippon Kayaku Co., Ltd.), except that the polymerizable composition was prepared in the same manner as in Example 101. For each polymerizable compound, a photocured film was prepared in the same manner as in Example 101, and the light resistance and solvent resistance were evaluated. Both were evaluated as A on the evaluation criteria, and the performance was good.

[0223] (Example 201): Polymer P-1

[0224]

[0225] Polymer P-1 was produced according to the above scheme. First, 100 mg of compound Z-39 (maximum absorption wavelength (in ethyl acetate solution): 418 nm) obtained in Example 1, 9.9 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added to a 200 mL three-neck flask, and the mixture was stirred at 80°C for 30 minutes under a nitrogen stream. 200 mg of 2,2'-azobis(isobutyrate)dimethyl (V-601, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. (hereinafter referred to as V-601)) was added to this solution, and the mixture was stirred at 80°C for 6 hours and then cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropyl alcohol and allowed to stand overnight. The precipitate that separated out was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. 140 mL of hexane and 60 mL of isopropyl alcohol were added to the obtained powder, and the mixture was stirred at room temperature for 1 hour and then allowed to stand at room temperature overnight. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50°C to obtain 7.0 g of the target polymer P-1. The number average molecular weight of the obtained polymer P-1 was 26,000 (polystyrene equivalent). 100 mg of the obtained polymer P-1 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelength of polymer P-1 was 420 nm (absorbance 0.77).

[0226] (Example 202): Polymer P-2

[0227] Polymer P-2 was produced according to the above scheme. First, 100 mg of compound Z-39 (maximum absorption wavelength (in ethyl acetate solution): 418 nm) obtained in Example 1, 100 mg of 2-[2-hydroxy-5-(2-methacryloyloxyethyl)phenyl]2H-benzo[d][1,2,3]triazole (maximum absorption wavelength (in ethyl acetate solution): 338 nm) as an ultraviolet absorber, 9.8 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added to a 200 mL three-neck flask, and the mixture was stirred at 80°C for 6 hours under a nitrogen stream and then cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropyl alcohol and left overnight. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. 140 mL of hexane and 60 mL of isopropyl alcohol were added to the obtained powder, and the mixture was stirred at room temperature for 1 hour and then left at room temperature overnight. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50°C to obtain 5.0 g of the target polymer P-2. The number average molecular weight of the obtained polymer P-2 was 32,400 (polystyrene equivalent). 150 mg of the obtained polymer P-2 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelengths of polymer P-2 were 420 nm (absorbance 1.11) and 344 nm (absorbance 1.05). Polymer P-2 was capable of sufficiently blocking light in the blue light region. Furthermore, it also had excellent blocking properties for light with wavelengths shorter than 350 nm. In addition, it had high transmittance in the wavelength range of 360 nm to 380 nm, and was presumed to be advantageous for UV curing.

[0228] (Example 203): Polymer P-3

[0229] Polymer P-3 was produced according to the above scheme. First, 160 mg of compound Z-39 obtained in Example 1 (maximum absorption wavelength (in ethyl acetate solution): 418 nm), 40 mg of bis(2-(methacryloyloxy)ethyl)4,4'-((2-(1,2-dibenzyl-3,5-dioxopyrazolidin-4-ylidene)-5-methylbenzo[d][1,3]dithiol-4,7-diyl)bis(oxy))dibutyrate (maximum absorption wavelength (in ethyl acetate solution): 387 nm) as an ultraviolet absorber, 9.8 g of methyl methacrylate, and 40.0 g of propylene glycol monomethyl ether acetate were added to a 200 mL three-neck flask, and the mixture was stirred at 80°C for 6 hours under a nitrogen stream and then cooled to room temperature. The resulting reaction mixture was slowly added to a mixture of 140 mL of hexane and 60 mL of isopropyl alcohol and allowed to stand overnight. The precipitate was collected by filtration and washed with a mixture of hexane and isopropyl alcohol. 140 mL of hexane and 60 mL of isopropyl alcohol were added to the obtained powder, and the mixture was stirred at room temperature for 1 hour and then left to stand at room temperature overnight. The precipitate was collected by filtration, washed with a mixture of hexane and isopropyl alcohol, and dried at 50°C to obtain 5.8 g of the target polymer P-3. The number average molecular weight of the obtained polymer P-3 was 33,900 (polystyrene equivalent). 150 mg of the obtained polymer P-3 was dissolved in 100 mL of chloroform, and the absorption spectrum was measured. The maximum absorption wavelengths of polymer P-3 were 420 nm (absorbance 1.61) and 390 nm (absorbance 1.38). Polymer P-3 was capable of blocking a wide range of light from UV to blue light.

[0230] (Example 301): Cured film (resin film) 500 mg of the polymer P-1 produced in Example 201, 7.6 g of chloroform, and 1.1 g of polymethyl methacrylate resin (Dianal BR-80 (containing 60% by mass or more of methyl methacrylate as a monomer unit, weight average molecular weight: 95,000, acid value: 0 mg KOH / g, manufactured by Mitsubishi Chemical Corporation) was dissolved to prepare a resin composition (dye composition). The obtained resin composition was spin-coated onto a glass substrate, and the coated film was dried at 60 ° C. for 2 minutes to form a resin film 1 containing the polymer P-1 and having a thickness of about 10 μm. The polymer P-1 was changed to the polymer P-2 produced in Example 202 or the polymer P-3 produced in Example 203, and resin film 2 or resin film 3 was produced in the same manner, respectively.

[0231] (Evaluation 2) - Lightfastness - For each of Resin Films 1 to 3 produced in Example 301, the absorbance retention rate at the maximum absorption wavelength (λmax, unit: nm) was determined under the following conditions and used as an index for evaluating lightfastness. Specifically, the absorbance of the cured film at λmax was measured using a spectrophotometer (UV-1900PC, manufactured by Shimadzu Corporation), and then the cured film was subjected to a lightfastness test under the following conditions. The absorbance of the cured film after the lightfastness test at λmax was measured. Next, the absorbance retention rate L2 (%) was calculated using the absorbance values ​​at λmax of the cured film before and after the lightfastness test according to the following formula 8, and lightfastness was evaluated. A higher absorbance retention rate L2 indicates better lightfastness. The evaluation results are shown in the lightfastness column of Table 9.

[0232] Absorbance retention rate L2 (%) = (absorbance at λmax of photocured film after light resistance test / absorbance at λmax of photocured film before light resistance test) × 100 Formula 8

[0233] -Conditions- Apparatus: Low-temperature cycle xenon weather meter (manufactured by Suga Test Instruments Co., Ltd.: XL75) Illuminance: 90 klx (40 w / m ２ ) Time: 24 hours Environment: 23°C, relative humidity 50%

[0234]

[0235] Compounds 1 to 25 (dyes represented by Formula 1) synthesized according to the above had a maximum absorption wavelength in the wavelength range of 350 nm to 450 nm and were compounds exhibiting UV and blue light blocking properties. Some of the compounds had a maximum absorption wavelength in the wavelength range of 400 nm to 450 nm and were found to be useful dyes because they absorb light in the long wavelength region of blue light with a molar absorption coefficient sufficient for dyes, etc. For example, by combining Compound 18, which has a maximum absorption wavelength at 433 nm, with an ultraviolet absorber, a dye can be obtained that has blocking properties over a wide wavelength range, from ultraviolet light to the long wavelength region of blue light. Furthermore, as shown in Table 8 or Table 9, in Examples 6 and 10 using specific dyes, photocured films and the like could be formed as molded products of the polymerizable composition or resin composition, and the formed photocured films or resin films had excellent light resistance and solvent resistance. In contrast, in Comparative Example 1 using the comparative dye T-1, the resin film formed did not have the same level of light resistance and solvent resistance as the resin film of the present disclosure.

[0236] The dye composition, compound, dye, blue light blocking agent, polymer, and cured product of the present disclosure can each be applied to optical materials. Optical materials include optical filters (e.g., optical lenses), optical films, and optical sheets (including protective sheets). Specific examples of optical materials include blue light-cutting materials that block or suppress blue light in the visible light range (e.g., blue light-cutting lenses (e.g., eyeglasses, contact lenses)); UV-cutting materials that block or suppress ultraviolet (UV) light (e.g., UV-cutting lenses (e.g., eyeglasses, contact lenses); partial blocking materials that block blue light and ultraviolet light and transmit violet light and the like (e.g., eyeglasses, contact lenses); UV-cutting films or sheets (e.g., window films, display films for various image display devices, display films for mobile terminals (smartphones, tablets, etc.)); and UV-cutting glass (e.g., vehicle glass, building glass, etc.). For example, the optical materials are suitable for applications such as improving the durability of LCDs and organic EL devices. In particular, they are suitable for use in environments requiring light resistance and solvent resistance. Furthermore, the dye compositions, compounds, dyes, blue-screening agents, and polymers of the present disclosure are suitable for use in environments requiring heat resistance and light resistance, and can be suitably used in applications such as dye monomers, dye polymers, inks, and paints. Examples of image display devices include liquid crystal displays (LCDs), plasma display panels, electroluminescence (EL) displays, and cathode ray tube display devices. Furthermore, image display devices include not only large-area image display devices but also portable terminals such as smartphones or tablet terminals equipped with touch panels. There are no particular limitations on the touch panel, and it can be appropriately selected depending on the purpose. Examples of touch panels include surface-type capacitive touch panels, projected capacitive touch panels, and resistive touch panels. Touch panels also include so-called touch sensors and touch pads.

[0237] The disclosure of Japanese Patent Application No. 2023-223506, filed on December 28, 2023, is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A dye composition containing a dye represented by the following formula 1. In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group, and R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and R ４ represents a hydrogen atom, an alkyl group, an aryl group, or an amino group. R ５ and R ６ may be bonded to each other to form a 6-membered ring. However, at least one of R １ to R ６ is a group containing a polymerizable group having an ethylenic unsaturated bond.

2. The pigment is R １ and R ２ The pigment composition according to claim 1, wherein each independently represents an alkyl group or a phenyl group.

3. The pigment is R １ ~R ６ The pigment composition according to claim 1, wherein at least one of them is a group containing the polymerizable group and is a group containing a (meth)acryloyloxy group or a vinylphenyl group.

4. The pigment composition according to claim 1, comprising a polymerizable compound which is a compound different from the pigment.

5. The pigment composition according to claim 1, comprising a copolymer of the pigment and a polymerizable compound which is a compound different from the pigment.

6. The pigment composition according to claim 1, comprising a photoinitiator.

7. The pigment composition according to claim 1, comprising a resin.

8. The pigment composition according to claim 1, comprising a light-absorbing compound having a maximum absorption wavelength on the shorter wavelength side than the pigment.

9. A compound represented by the following formula 1. In formula 1, R １ and R ２ each independently represent an alkyl group or an aryl group, and R ３ , R ５ and R ６ each independently represent a hydrogen atom, an alkyl group or an aryl group, and R ４ represents a hydrogen atom, an alkyl group, an aryl group or an amino group. R ５ and R ６ may be bonded to each other to form a 6-membered ring. However, at least one of R １ to R ６ is a group containing a polymerizable group having an ethylenic unsaturated bond.

10. A dye represented by the following formula (1). In formula (1), R １ and R ２ each independently represents an alkyl group or an aryl group, and R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group or an aryl group, and R ４ represents a hydrogen atom, an alkyl group, an aryl group or an amino group. R ５ and R ６ may be bonded to each other to form a 6-membered ring. However, at least one of R １ to R ６ is a group containing a polymerizable group having an ethylenically unsaturated bond.

11. A blue light-shielding agent represented by the following formula (1). In formula (1), R １ and R ２ each independently represent an alkyl group or an aryl group, R ３ , R ５ and R ６ each independently represent a hydrogen atom, an alkyl group or an aryl group, and R ４ represents a hydrogen atom, an alkyl group, an aryl group or an amino group. R ５ and R ６ may be bonded to each other to form a 6-membered ring. However, at least one of R １ to R ６ is a group containing a polymerizable group having an ethylenic unsaturated bond.

12. A polymer comprising a structural unit derived from the compound according to claim 9.

13. A cured product obtained by the pigment composition according to claim 1.

14. An optical material comprising the cured product according to claim 13.

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