Composition, resin composition, liquid composition, dye compound, and optical material

Abstract

The present invention pertains to: a composition containing a dye represented by formula 1 and at least one ultraviolet absorber selected from the group consisting of benzotriazole-based compounds, triazine-based compounds, benzophenone-based compounds, merocyanine-based compounds, cyanine-based compounds, acrylate-based compounds, benzoxazinone-based compounds, benzoxazole-based compounds, and benzodithiol-based compounds; and a resin composition, a liquid composition, a dye compound, and an optical material. In formula 1, R1 and R2 each independently represent an alkyl group or an aryl group, R3, R4, R5, and R6 each independently represent a hydrogen atom or a substituent, and R5 and R6 are optionally bonded to each other to form a six-membered ring.

Description

Composition, resin composition, liquid composition, dye compound, and optical material

[0001] The present disclosure relates to a composition, a resin composition, a liquid composition, a dye compound, and an optical material.

[0002] Ultraviolet rays in the wavelength range from the visible light range to the short wavelength side, and blue light (so-called blue light) emitted from displays of various image display devices, etc., are of concern as they may have an effect on the human body (especially the eyes).

[0003] To protect against ultraviolet (UV) rays, UV-cutting materials such as glass, film, and eyeglass lenses that use components that absorb UV rays, as well as UV care cosmetics, sunscreens, and other daily necessities, are available.

[0004] Furthermore, in recent years, attention has been focused on the effects on the eyes of blue light contained in the light emitted from the displays of image display devices such as liquid crystal display devices or the displays of mobile devices such as smartphones, and eye strain caused by blue light has become a problem. Therefore, optical materials such as eyeglass lenses and protective films that contain components that absorb not only ultraviolet light but also blue light with wavelengths of 380 nm to 450 nm have been proposed.

[0005] Optical materials containing components responsible for absorbing ultraviolet and blue light are often used in environments where they are continuously exposed to light such as sunlight or in high-temperature environments, such as in eyeglass lenses, protective films, and vehicle windows, etc. Therefore, it is desirable for the components responsible for absorbing ultraviolet and blue light to have a certain degree of fastness to light and heat.

[0006] A resin composition has been proposed that has blocking properties for ultraviolet light and blue light with wavelengths of 380 nm to 450 nm, and that has good light resistance and durability. The resin composition contains a dye having a structure in which a pyrazolidinedione skeleton and a pyrrole skeleton are linked by a methine group (see International Publication No. 2020 / 20291).

[0007] Conventionally, technologies for blocking ultraviolet light and blue light have been studied. The resin composition described in International Publication No. 2020 / 20291 achieves a certain level of light resistance and durability. However, when a specific dye compound is used in combination with an ultraviolet absorber, the dye compound and the ultraviolet absorber may interact over time, causing aggregation of the components. The present inventors have found that there is a problem in that it is difficult to incorporate the dye compound and the ultraviolet absorber into the composition in a sufficient amount to obtain the required performance.

[0008] The problem to be solved by one embodiment of the present disclosure is to provide a composition that has high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and has excellent light resistance and heat resistance. The problem to be solved by another embodiment of the present disclosure is to provide a resin composition and a liquid composition that have high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and has excellent light resistance and heat resistance. The problem to be solved by another embodiment of the present disclosure is to provide a novel dye compound that has high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and has excellent light resistance and heat resistance. The problem to be solved by another embodiment of the present disclosure is to provide an optical material that has high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and is suitable for use in light-exposed and high-temperature environments.

[0009] Specific means for solving the problems include the following aspects: <1> A composition containing a dye represented by the following formula 1 and at least one ultraviolet absorber selected from the following compound group I.

[0010]

[0011] In Formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent, R ５ and R ６may be bonded to each other to form a 6-membered ring. -Compound Group I- Benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, acrylate compounds, benzoxazinone compounds, benzoxazole compounds, benzodithiol compounds

[0012] <2> The composition according to <1>, wherein the ultraviolet absorber includes at least one compound selected from the group consisting of compounds represented by the following formula (2-1), formula (2-2), formula (2-3), and formula (2-4):

[0013]

[0014] In formula (2-1), R １１ and R １２ each independently represents a hydrogen atom or a substituent, and n11 and n12 each independently represent an integer of 1 to 3. In formula (2-2), R ２１ and R ２２ each independently represents a hydrogen atom or a substituent, and n21 and n22 each independently represent an integer of 1 to 3. In formula (2-3), R ３１ , R ３２ and R ３３ each independently represents a hydrogen atom or a substituent, and n31, n32, and n33 each independently represents an integer of 1 to 3. In formula (2-4), R ４１ , R ４２ , R ４３ , R ４４ , R ４５ , R ４６ and R ４７ each independently represents a hydrogen atom or a substituent.

[0015] <3> The composition according to <1> or <2>, wherein a content ratio of the dye to the ultraviolet absorber is in a range of 1:20 to 20:1 by mass. <4> A resin composition comprising a dye represented by the following formula 1, at least one ultraviolet absorber selected from the following compound group I, and a resin.

[0016]

[0017] In Formula 1, R １ and R ２each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent, R ５ and R ６ may be bonded to each other to form a 6-membered ring. -Compound Group I- Benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, acrylate compounds, benzoxazinone compounds, benzoxazole compounds, benzodithiol compounds

[0018] <6> A liquid composition comprising a dye represented by the following formula 1, at least one ultraviolet absorber selected from the following compound group I, and a solvent.

[0019]

[0020] In Formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent, R ５ and R ６ may be bonded to each other to form a 6-membered ring. -Compound Group I- Benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, acrylate compounds, benzoxazinone compounds, benzoxazole compounds, benzodithiol compounds

[0021] <6> The composition according to any one of <1> to <5>, further comprising at least one anti-fading agent selected from the group consisting of an amine compound, a phenol compound, a hydroquinone compound, a catechol compound, an ascorbic acid compound, a carotenoid compound, a metal complex compound, and a benzolactone compound. <7> The composition according to <6>, wherein the content ratio of the dye to the anti-fading agent is in the range of 1:20 to 20:1 by mass. <8> The composition according to <6> or <7>, wherein the anti-fading agent comprises at least one compound selected from the group consisting of compounds represented by the following formula (3-1) or formula (3-2):

[0022] In formula (3-1), R ａ１ , R ａ２ , R ａ３ and R ａ４ each independently represents a hydrogen atom, an alkyl group, or an alkenyl group; ａ１ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group or an oxy radical group; X ａ２ represents an atomic group necessary to form a 5- to 7-membered ring. ｐ１ represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or —Si(R ｐ１０１ ) (Rp １０２ ) (Rp １０３ ) and R ｐ１０１ , Rp １０２ and Rp １０３ each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, or an aryloxy group; Rｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ each independently represents a hydrogen atom or a substituent, ｐ１ , R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ two adjacent groups among R may be bonded to form a ring; ｐ１ , R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ <9> An optical material that is a cured product of the composition according to any one of <1>, <2>, <3>, <6>, <7>, and <8>, the resin composition according to <4>, or the liquid composition according to <5>. <10> A dye compound represented by the following formula 4:

[0023]

[0024] In Formula 4, R ４１ represents a hydrogen atom, an alkyl group, or an aryl group. ４１ When represents a hydrogen atom, R ４２ represents a secondary alkyl group having a branched structure at the carbon atom directly bonded to the nitrogen atom, a tertiary alkyl group having a branched structure at the carbon atom directly bonded to the nitrogen atom, or an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms; R ４１ represents an alkyl group or an aryl group, R ４２ represents a hydrogen atom or a substituent. ４３ , R ４４ , R ４５ and R ４６ each independently represents a hydrogen atom or a substituent. <11> A dye compound represented by the following formula 5:

[0025]

[0026] In Formula 5, R ５１ represents a hydrogen atom, a methyl group, or a phenyl group. ５１ When represents a hydrogen atom, R５２ represents a secondary alkyl group having a branched structure at the carbon atom directly bonded to the nitrogen atom, a tertiary alkyl group having a branched structure at the carbon atom directly bonded to the nitrogen atom, or an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms; R ５１ represents a methyl group or a phenyl group, R ５２ represents a hydrogen atom or a substituent.

[0027] <12> An optical material containing the dye compound according to <10> or <11>. <13> The optical material according to <12>, which is a spectacle lens. <14> The optical material according to <12>, which is a protective sheet.

[0028] According to one embodiment of the present disclosure, a composition is provided that has high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and has excellent light resistance and heat resistance. According to another embodiment of the present disclosure, a resin composition and a liquid composition are provided that have high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and have excellent light resistance and heat resistance. According to another embodiment of the present disclosure, a novel dye compound is provided that has high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and has excellent light resistance and heat resistance. According to another embodiment of the present disclosure, an optical material is provided that has high absorbance in the ultraviolet light region and at least a wavelength region of 350 nm to 450 nm, and is suitable for use in light-exposed and high-temperature environments.

[0029] 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 such embodiments.

[0030] 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.

[0031] 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.

[0032] In the present disclosure, when a layer contains multiple substances corresponding to each component, the amount of each component in the composition refers to the total amount of the multiple substances present in the composition, unless otherwise specified. In the present disclosure, the term "total solid content" refers to the total mass of the components excluding the solvent from the entire composition. As described above, the "solid content" refers to the components excluding the solvent, and may be, for example, solid or liquid at 25°C.

[0033] In the present disclosure, a combination of preferred aspects is a more preferred aspect.

[0034] <Composition> The composition of the present disclosure contains a dye represented by the following formula 1 (hereinafter also referred to as a specific dye) and at least one ultraviolet absorber selected from the following compound group I (hereinafter also referred to as a specific UV agent). The composition of the present disclosure may further contain, as necessary, a dye other than the specific dye, an ultraviolet absorber not included in the specific UV agent, and other components.

[0035] As represented by Formula 1, a specific dye having a structure in which a pyrazolidinedione skeleton and a pyrrole skeleton are linked by a methine group has high absorption, particularly in the wavelength region of 350 nm to 450 nm, and is robust to heat and light. Furthermore, the present inventors have discovered that by including a specific dye and a specific UV agent in the composition of the present disclosure, aggregation due to interaction between the specific dye and the specific UV agent in the composition is suppressed, allowing the contents of the specific dye and the specific UV agent in the composition to be increased, thereby improving the flexibility of formulation of the composition. Because the composition of the present disclosure includes the specific dye represented by Formula 1, it has high absorbance for light with wavelengths of at least 350 nm to 450 nm and is excellent in light fastness and heat resistance.

[0036] As described below, the composition of the present disclosure can be suitably applied to resin compositions containing resins, liquid compositions containing solvents, and the like.

[0037] (Dye Represented by Formula 1) The composition of the present disclosure contains a dye represented by Formula 1 (i.e., a specific dye). The specific dye is a yellow dye that has high absorbance in at least a wavelength region of 350 nm to 450 nm within a wavelength region of 280 nm to 500 nm. In particular, a yellow dye that has high absorbance in a wavelength region of 380 nm to 450 nm is preferred. The specific dye in the present disclosure includes dyes and pigments.

[0038]

[0039] In Formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent, R ５ and R ６ may be bonded to each other to form a six-membered ring.

[0040] R １ and R ２ The alkyl group in the formula (I) may be either an unsubstituted alkyl group or a substituted alkyl group.

[0041] The unsubstituted alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, and a cyclohexyl group.

[0042] Examples of the substituent of the substituted alkyl group include the substituents included in the following substituent group A. (Substituent group A) Halogen atoms, alkyl groups (including linear, branched, and cyclic alkyl groups), aralkyl groups, alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, cyano groups, hydroxy groups, nitro groups, carboxy 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, anilino groups, alkylamino groups, acylamino groups, aminocarbonylamino groups, alkylcarbonylamino groups, alkoxycarbonylamino groups, alkoxycarbonylamino groups, alkoxycarbonylamino groups, aryloxycarbonyloxy ... amino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, sulfonamide group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group (which may be in the form of a salt), alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imido group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, etc.

[0043] 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.

[0044] The substituted alkyl group is preferably a substituted 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.

[0045] In addition, R １ and R ２ When both represent alkyl groups, the alkyl groups may be the same or different.

[0046] R １ and R ２ The aryl group in may be either an unsubstituted aryl group or a substituted aryl group.

[0047] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, such as a phenyl group.

[0048] 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, and 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., a methyl group, an ethyl group, a normal propyl group, and an isopropyl group), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms; e.g., a methoxy group, an ethoxy group, a normal propoxy group, and an isopropoxy group), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; e.g., a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, and an isopropoxycarbonyl group), a sulfonyloxy group, and a monovalent group in which at least two of these are linked together.

[0049] 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.

[0050] In addition, R １ and R ２ When both represent aryl groups, the aryl groups may be the same or different.

[0051] R ３ , R ４ , R ５ and R ６Examples of the substituent in the group R include those included in the group A of substituents. ３ , R ５ and R ６ is preferably an alkyl group or an aryl group. ３ , R ５ and R ６ and each independently preferably represents a hydrogen atom, an alkyl group, or an aryl group. ４ is preferably an alkyl group, an aryl group, or an amino group. ４ is preferably a hydrogen atom, an alkyl group, an aryl group, or an amino group.

[0052] 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.

[0053] The unsubstituted alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, a normal propyl group, and an isopropyl group.

[0054] R ３ , R ５ and R ６ 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, and a hydroxy group. The substituted alkyl group substituted with a substituent is preferably an alkyl group having a total of 1 to 8 carbon atoms, and examples thereof include a benzyl group, a carboxymethyl group, and a hydroxymethyl group.

[0055] In addition, R ３ , R ５ and R ６ When both represent alkyl groups, the alkyl groups may be the same or different.

[0056] R ３ , R ５ and R ６The aryl group in may be either an unsubstituted aryl group or a substituted aryl group.

[0057] The unsubstituted aryl group is preferably an aryl group having 6 to 10 carbon atoms, such as a phenyl group.

[0058] 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, and an iodine atom), a hydroxy group, a carboxy group, and an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; e.g., a methyl group, an ethyl group, a normal propyl group, and an isopropyl group).

[0059] 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.

[0060] R ５ and R ６ is a substituent, from the viewpoint of light resistance and heat 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.

[0061] R ４ The alkyl group in the formula (I) may be either an unsubstituted alkyl group or a substituted alkyl group.

[0062] The unsubstituted alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, and a cyclohexyl group.

[0063] R ４Examples 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, a methyl group, an ethyl group, a normal propyl group, and an isopropyl group), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms; for example, a methoxy group, an ethoxy group, a normal propoxy group, and an isopropoxy group), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; for example, a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, and an isopropoxycarbonyl group), an alkylamino group (preferably an alkylamino group having 1 to 4 carbon atoms; for example, a dimethylamino group), an alkylcarbonylamino group (preferably an alkylcarbonylamino group having 1 to 4 carbon atoms; for example, a methylcarbonylamino group), a cyano group, and a monovalent group in which at least two of these are linked together.

[0064] 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.

[0065] R ４ The aryl group in may be either an unsubstituted aryl group or a substituted aryl group.

[0066] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, such as a phenyl group.

[0067] R ４Examples 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, and 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., a methyl group, an ethyl group, a normal propyl group, and an isopropyl group), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms; e.g., a methoxy group, an ethoxy group, a normal propoxy group, and an isopropoxy group), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; e.g., a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, and an isopropoxycarbonyl group), a sulfonyloxy group, and a monovalent group in which at least two of these are linked together.

[0068] 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, or a 4-methoxyphenyl group. , 4-ethoxyphenyl group, 4-(2-hydroxyethoxy)phenyl group, N,N-dimethylaminophenyl group, N,N-diethylaminophenyl group, 4-(N-carboxymethyl-N-ethylamino)phenyl group, 4-{N,N-di(ethoxycarbonylmethyl)amino}phenyl group, 4-{di(ethoxycarbonylmethyl)amino}carbonylphenyl, 4-ethoxycarbonylphenyl group, 4-methanesulfonyloxyphenyl group, 4-acetylsulfamoylphenyl, 4-propionylsulfamoylphenyl, and 4-methanesulfonamidophenyl.

[0069] R ４The amino group in may be either an unsubstituted amino group or a substituted amino group.

[0070] 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. The alkylamino group is preferably an alkylamino group having 1 to 8 carbon atoms, more preferably an alkylamino group having 1 to 4 carbon atoms, and examples thereof include a methylamino group, a dimethylamino group, a diethylamino group, and a pyrrolidino group.

[0071] 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.

[0072] R in Formula 1 １ and R ２ Among them, R １ is preferably an alkyl group or a phenyl group from the viewpoint of light resistance, and more preferably an alkyl group or an unsubstituted phenyl group.

[0073] In addition, from the viewpoint of further improving the stability of the composition when used in combination with a specific UV agent described below and further increasing the content of the specific UV agent, １ and R ２ are more preferably alkyl groups or unsubstituted phenyl groups, even more preferably alkyl groups having 1 to 8 carbon atoms or benzyl groups, and particularly preferably benzyl groups. １ and R ２ When each independently represents an aryl group, R ３ , R ５ and R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and R ３ and R ６ It is preferable that at least one of R represents a hydrogen atom. ３ represents a hydrogen atom, R ５ and R６ More preferably, each independently represents an alkyl group or an aryl group, and R ３ represents a hydrogen atom, R ５ and R ６ More preferably, each independently represents an alkyl group, and R ３ represents a hydrogen atom, R ５ and R ６ each independently represents an alkyl group, and R ５ and R ６ are bonded to each other to form a ring, which is condensed with a pyrrole ring to form an indole ring together with the pyrrole ring. That is, it is particularly preferable that the specific dye has a structure shown in the following formula 1-1.

[0074]

[0075] R in Formula 1-1 １ ~R ４ is R in formula 1 １ ~R ４ and preferred embodiments are also the same.

[0076] Among them, R ３ is preferably a hydrogen atom, a methyl group, or a phenyl group. ３ When R is a hydrogen atom, the absorption in the long wavelength region of the composition becomes sharper, and when R is a methyl group, the light resistance of the composition is further improved. ３ is a hydrogen atom, R ４ is preferably a secondary alkyl group in which the carbon atom directly bonded to the nitrogen atom has a branch, a tertiary alkyl group in which the carbon atom directly bonded to the nitrogen atom has a branch, or an alkyl group having an electron-withdrawing group. ４ When the carbon atom directly bonded to the nitrogen atom is a branched secondary alkyl group, the dye compound has sharper absorption in the long wavelength region, and when the alkyl group has an electron-withdrawing group, the dye compound has improved light resistance.

[0077] R ４In another preferred embodiment, the carbon atom adjacent to the nitrogen atom is an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms. When the carbon atom adjacent to the nitrogen atom is an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms, the crystallization properties of the synthetic intermediate are improved, and purification efficiency is improved, resulting in an improved yield, compared to a primary alkyl group in which the carbon atom adjacent to the nitrogen atom has a substituent, or a substituent in which a carbon atom more distant from the nitrogen atom than the carbon atom adjacent to the nitrogen atom has a branch, for example, a substituent in which a carbon atom having 8 carbon atoms has a branch and is more distant from the nitrogen atom.

[0078] R １１ ~R １４ R each independently represents a hydrogen atom or a substituent. １１ ~R １４ When R represents a substituent, examples of the substituent include the substituents included in the above-mentioned substituent group A. １１ ~R １４ From the viewpoint of making the absorption of the dye compound in the long wavelength region sharper, R is preferably a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, an amino group, or an alkylamino group. １１ ~R １４ Among these, it is preferable that two to four represent hydrogen atoms.

[0079] R １１ ~R １４ From the viewpoint of improving the light resistance of the composition, R is also preferably a hydrogen atom or an electron-withdrawing group, and preferred examples of the electron-withdrawing group include a halogen atom, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, and an arylsulfonyl group halogen atom. １１ ~R １４ Among these, it is preferable that two to four represent hydrogen atoms.

[0080] Specific examples of the dye represented by the above formula 1 (i.e., the specific dye) are shown below. However, the present disclosure is not limited to these specific examples. In the following specific examples, Me represents a methyl group, and Ph represents a phenyl group.

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] Synthesis The dye (specific dye) represented by Formula 1 can be synthesized by a known method. For the synthesis method of the specific dye, reference can be made to paragraphs

[0073] to

[0078] of International Publication No. 2020 / 20291, for example. An example of the synthesis method is a method in which pyrazolidinedione and aldehyde are mixed in an organic solvent under room temperature (25°C) or reflux conditions. The synthesis of the specific dye will be described in detail in the Examples.

[0098] Examples of organic solvents used in the synthesis include alcohols (eg, methanol and ethanol), acetonitrile, N,N-dimethylformamide (DMF), pyridine, acetic acid, and acetic anhydride.

[0099] A catalyst may be added during the synthesis of a specific dye, and examples of the catalyst include piperidine, glycine, β-alanine, p-toluenesulfonic acid, and ammonium acetate.

[0100] After refluxing, the mixture may be cooled to room temperature (i.e., 25°C) to precipitate the specific dye in a solid form. 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 to wash the solid.

[0101] The composition of the present disclosure may contain one type of dye represented by Formula 1 (i.e., specific dye) alone, or may contain two or more types. The content of the dye represented by Formula 1 (i.e., specific dye) in the composition of the present disclosure is not particularly limited and may be appropriately selected depending on the intended use of the composition. For example, when the composition of the present disclosure is made into a resin composition further containing a resin, the content of the specific dye can be 0.01% by mass to 25% by mass, and preferably 0.1% by mass to 5% by mass, based on the total solid content of the resin composition.

[0102] The dye represented by Formula 1 (i.e., the specific dye) has particularly high absorbance in the wavelength region of 350 nm to 450 nm, and therefore, when the content of the specific dye in the resin composition of the present disclosure is within the above range, the resin composition of the present disclosure becomes a resin composition excellent in blocking or suppressing light with wavelengths of 350 nm to 450 nm. The specific dye can effectively block or suppress, for example, ultraviolet light and blue light.

[0103] (At least one ultraviolet absorber selected from compound group I) The composition of the present disclosure contains at least one ultraviolet absorber (i.e., specific UV agent) selected from compound group I. - Compound group I - Benzotriazole-based compounds, triazine-based compounds, benzophenone-based compounds, merocyanine-based compounds, cyanine-based compounds, acrylate-based compounds, benzoxazinone-based compounds, benzoxazole-based compounds, benzodithiol-based compounds

[0104] Examples of specific UV agents include the compounds shown below. Benzoxazole-based 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-based compounds include, for example, the compounds described in Japanese Patent Nos. 5,591,453 and 5,250,289. Merocyanine-based compounds include, for example, the compounds described in JP-A-2011-184414. Benzodithiol-based compounds include, for example, the compounds described in Japanese Patent Nos. 5,450,994 and 5,364,311. Specific examples of benzoxazinone-based compounds include UV-1, UV-2, UV-3, and the like, which have the following structures:

[0105]

[0106] Specific examples of merocyanine compounds include UV-4 and UV-5 having the following structures:

[0107]

[0108] Specific examples of benzoxazole compounds include UV-6 and UV-7 having the following structures:

[0109]

[0110] Specific examples of the benzodithiol compounds include UV-8 and UV-9 having the following structures:

[0111]

[0112] Among the specific UV agents included in compound group I, from the viewpoint of effectiveness, ultraviolet absorbers having a maximum absorption wavelength of 350 nm or less are preferred, and benzotriazole-based compounds, triazine-based compounds, and benzophenone-based compounds are preferred. More specifically, the specific UV agent preferably contains at least one selected from the group consisting of compounds represented by the following formula (2-1), formula (2-2), formula (2-3), and formula (2-4):

[0113]

[0114] In formula (2-1), R １１ and R １２ each independently represents a hydrogen atom or a substituent, and n11 and n12 each independently represent an integer of 1 to 3. In formula (2-2), R ２１ and R ２２ each independently represents a hydrogen atom or a substituent, and n21 and n22 each independently represent an integer of 1 to 3. In formula (2-3), R ３１ , R ３２ and R ３３ each independently represents a hydrogen atom or a substituent, and n31, n32, and n33 each independently represents an integer of 1 to 3. In formula (2-4), R ４１ , R ４２ , R ４３ , R ４４ , R ４５ , R ４６ and R ４７ each independently represents a hydrogen atom or a substituent.

[0115] The specific UV agent represented by formula (2-1) is a compound included in benzophenone-based compounds. １１ and R １２ When each independently represents a substituent, examples of the substituents include those included in the above-mentioned Substituent Group A. Among them, examples of the substituent include a halogen atom, a hydroxyl group, an alkyl group, a phenyl group, an alkoxy group, an alkylsulfonyl group, an arylsulfonyl group, a sulfonic acid group, an alkyloxycarbonyl group, an aryloxycarbonyl group, and an amino group. Each of n11 and n12 independently represents an integer of 1 to 3, preferably 1 to 2. The above-mentioned alkyl group, phenyl group, alkoxy group, alkylsulfonyl group, arylsulfonyl group, alkyloxycarbonyl group, aryloxycarbonyl group, and amino group may each be substituted or unsubstituted.

[0116] For details of the compound represented by formula (2-1), reference can be made to the compound represented by general formula (IVa) described in paragraphs

[0180] to

[0195] of JP-A No. 2009-96974 and the compound represented by general formula (2-a) described in paragraphs

[0089] to

[0092] of JP-A No. 2009-9270062, and the above descriptions can be applied to the present disclosure. More specific examples of the specific UV agent represented by formula (2-1) include 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 1,4-bis(4-benzoyl-3-hydroxyphenoxy)butane, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, and 2,2',4,4'-tetrahydroxybenzophenone. Among these, the compounds represented by the following (U3-1) and (U3-2) are preferred.

[0117]

[0118] The specific UV agent represented by formula (2-2) is a compound included in benzotriazole-based compounds. ２１ and R ２２ each independently represents a hydrogen atom or a substituent, R ２１ and R ２２ When represents a substituent, examples of the substituent include the substituents included in the above-mentioned substituent group A. Among them, examples of the substituent include R ２１ R is preferably a linear or branched alkyl group, a cycloalkyl group, or an aryl group. ２２ is a halogen atom, an alkyl group, an alkoxy group, or —COOR ２４ Preferably, R ２４represents a hydrogen atom, an alkyl group, or an aryl group. n21 and n22 each independently represent an integer of 1 to 3, and n21 is preferably 1 or 2, and more preferably 1. n22 is preferably 1 or 2, and more preferably 2. For details of the compound represented by formula (2-2), reference can be made to the compound represented by general formula (IIa) described in paragraphs

[0147] to

[0167] of JP-A-2009-96974, and the above description can be applied to the present disclosure.

[0119] Examples of the specific UV agent represented by formula (2-2) include 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole, 2-3(t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-5-t-octylphenyl)benzotriazole, 2-ethylhexyl-3-[3-t-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, 2-(2H-benzotriazol-2-yl)-3-t-butylphenol, 2-(2H-benzotriazol-2-yl)-6-(methyl- 1-phenylethyl)-4-(1,1-3,3-tetramethylbutyl)phenol, 2-(2H-benzotriazol-2-yl)-3-methylphenol, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, etc. Among these, the compounds represented by the following (U1-1), (U1-2), and (U1-3) are preferred.

[0120]

[0121] The specific UV agent represented by formula (2-3) is a compound included in the triazine-based compounds. ３１ , R ３２ and R ３３ each independently represents a hydrogen atom or a substituent, and n31, n32, and n33 each independently represents an integer of 1 to 3.

[0122] R ３１ , R３２ and R ３３ When represents a substituent, examples of the substituent include the substituents included in the above-mentioned substituent group A. Among them, examples of the substituent include a hydroxyl group, an alkyl group, an aryl group, or an alkoxy group. n31, n32, and n33 each independently represent an integer of 1 to 3, preferably 1 or 2, and more preferably 1. For details of the compound represented by formula (2-3), reference can be made to the compound represented by general formula (III) described in paragraphs

[0168] to

[0179] of JP-A-2009-96974, and the above description can be applied to the present disclosure. Specific examples of the compound represented by formula (2-3) include 2,4-bis(2-hydroxy-4-butoxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexyloxyphenol, and bisethylhexyloxyphenol methoxyphenyl triazine. Of these, the compounds represented by the following formulas (U2-1) and (U2-2) are preferred.

[0123]

[0124] In formula (2-4), R ４１ , R ４２ , R ４３ , R ４４ , R ４５ , R ４６ and R ４７ each independently represents a hydrogen atom or a substituent, R ４１ and R ４２ When R represents a substituent, examples of the substituent include the substituents included in the above-mentioned substituent group A. Among them, an alkyl group, an aryl group, or a heterocyclic group is preferable. ４１ and R ４２may be bonded to each other to form a ring containing a nitrogen atom.

[0125] The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, and examples thereof include a methyl group, an ethyl group, and a propyl group. The alkyl group may have a monovalent substituent at any position. Examples of the monovalent substituent include the substituents included in the above-mentioned substituent group A.

[0126] The aryl group is preferably an aryl group having 6 to 20 carbon atoms, such as a phenyl group or a naphthyl group. The aryl group may have a monovalent substituent at any position. Examples of the monovalent substituent include the substituents included in the above-mentioned substituent group A.

[0127] The heterocyclic group is preferably a heterocyclic group having 6 to 20 carbon atoms, and examples thereof include a pyridyl group, a piperidino group, and a morpholino group. The heterocyclic group may have a monovalent substituent at any position. Examples of the monovalent substituent include the substituents included in the above-mentioned substituent group A.

[0128] R ４１ and R ４２ may be bonded to each other to form a ring containing a nitrogen atom. The ring formed is preferably a nitrogen-containing 5- or 6-membered ring. Examples include a pyrrolidine ring, a pyrroline ring, an imidazolidine ring, an imidazoline ring, an oxazoline ring, a thiazoline ring, a piperidine ring, a morpholine ring, and a piperazine ring. These rings may have a monovalent substituent, and examples of the substituent include the substituents included in the above-mentioned substituent group A. Furthermore, they may form a condensed ring structure together with an aromatic ring or the like.

[0129] R ４３ and R ４４ When R represents a substituent, each independently represents a substituent having a Hammett's substituent constant σp value of 0.2 or more. ４３ and R ４４ may be bonded to each other to form a ring.

[0130] R ４５ , R ４６ and R ４７ represents a hydrogen atom or a monovalent substituent, R ４５ , R４６ and R ４７ When R represents a substituent, examples of the substituent include the substituents included in the above-mentioned substituent group A. ４１ , R ４５ , R ４６ and R ４７ Any two of the groups may be bonded to each other to form a ring.

[0131] R ４３ and R ４４ represents a substituent, R ４３ and R ４４ Each independently represents a substituent with a Hammett's substituent constant σp value of 0.2 or greater. The Hammett's substituent constant σ value will now be explained. Hammett's rule is an empirical rule proposed by L. P. Hammett in 1935 to quantitatively discuss the influence of substituents on the reaction or equilibrium of benzene derivatives, and it is now widely recognized as valid. The substituent constants determined by Hammett's rule include σp and σm values, and these values ​​can be found in many general textbooks. For example, see "Lange's Handbook of Chemistry," 12th Edition, 1979 (McGraw-Hill), edited by J. A. Dean; "The Domain of Chemistry," special edition, No. 122, pp. 96-103, 1979 (Nankodo); and Chem. Rev., Vol. 91, pp. 165-195, 1991, for detailed information. In the present disclosure, a substituent having a Hammett's substituent constant σp value of 0.2 or more indicates an electron-withdrawing group. The σp value is preferably 0.25 or more, more preferably 0.3 or more, and particularly preferably 0.35 or more.

[0132] R ４３ and R ４４ Examples of the hydroxyl group include a cyano group (0.66), a carboxyl group (-COOH: 0.45), an alkoxycarbonyl group (-COOMe: 0.45), an aryloxycarbonyl group (-COOPh: 0.44), a carbamoyl group (-CONH ２ : 0.36), alkylcarbonyl group (-COMe: 0.50), arylcarbonyl group (-COPh: 0.43), alkylsulfonyl group (-SO ２ Me: 0.72), or an arylsulfonyl group (—SO ２In the above substituents, Me represents a methyl group, and Ph represents a phenyl group. The values ​​in parentheses are the σp values ​​of representative substituents, excerpted from Chem. Rev., 1991, Vol. 91, pp. 165-195.

[0133] R ４３ and R ４４ may be bonded to each other to form a ring. ４３ , R ４４ Although it is not possible to define the σp value of R ４３ and R ４４ The σp value in the case of ring formation is defined by regarding each of the rings as being substituted with a partial structure. For example, when a 1,3-indandione ring is formed, R ４３ and R ４４ Each of these is considered to be substituted with a benzoyl group.

[0134] R ４５ , R ４６ and R ４７ represents a hydrogen atom or a monovalent substituent. Examples of the monovalent substituent include the substituents included in the above-mentioned substituent group A. ４５ , R ４６ and R ４７ is preferably a hydrogen atom, an alkyl group, an aryl group, or an alkoxy group.

[0135] R ４１ , R ４５ , R ４６ and R ４７ Any two groups among R may be bonded to each other to form a ring. ４１ and R ４５ or R ４５ and R ４７It is preferable that a ring is formed with a combination of the following. It is more preferable that the ring formed contains a carbon atom or nitrogen atom as already defined in the general formula (2-4) to form a 4- to 8-membered ring. For details of the compound represented by formula (2-4), reference can be made to the compound represented by general formula (1) described in paragraphs

[0047] to

[0086] of JP-A No. 2009-270062, and the above description can be applied to the present disclosure. Among these, the compound represented by formula (U4-1) is preferable.

[0136]

[0137] The composition of the present disclosure may contain only one type of specific UV agent, or may contain two or more types. From the viewpoint of the stability of the specific UV agent, it is preferable that the composition contains only one type of specific UV agent, or, if two or more types are contained, that the specific UV agents have the same main skeleton. The content of the specific UV agent in the composition of the present disclosure is not particularly limited and can be appropriately selected depending on the purpose of the composition. Generally, the content of the specific UV agent can be 0.01% by mass to 25% by mass, and preferably 0.1% by mass to 5% by mass, relative to the total solid content of the composition.

[0138] The present inventors have found that the inclusion of the specific dye and specific UV agent in the composition of the present disclosure improves the stability of both the specific dye and the specific UV agent. Specifically, they have found that even if the content of each of the specific dye and the specific UV agent is increased, the components are less likely to become unstable and the transparency of the composition is less likely to decrease over time due to aggregation of the specific dye and the specific UV agent. Although the mechanism of action is unclear, it is believed that this is because the specific dye and the specific UV agent contain ring structures, which inhibit the interaction between the components, making it difficult for adjacent components to aggregate even when the content of each component is increased.

[0139] By including a specific dye and a specific UV agent in the composition of the present disclosure, the stability of the specific UV agent is improved, and even when the content is increased, precipitation due to aggregation of the specific dye and the specific UV agent over time can be suppressed. From the viewpoint of further improving the effect of the combined use of the specific dye and the specific UV agent, the content ratio of the specific dye to the specific UV agent in the composition of the present disclosure is preferably in the range of 1:20 to 20:1 by mass, more preferably in the range of 1:10 to 10:1, and even more preferably in the range of 1:5 to 5:1. When the content ratio of the specific dye to the specific UV agent is in the above range, precipitation of the specific dye and the specific UV agent is effectively suppressed, and the content of the specific UV agent is in an appropriate range, resulting in a composition with good blocking effect from the ultraviolet region to the blue light region, i.e., the wavelength region of 450 nm.

[0140] The composition of the present disclosure may contain, in addition to the specific dye and specific UV agent described above, other components depending on the intended purpose. Examples of other components include dyes other than the specific dye (e.g., dyes and pigments), ultraviolet absorbers other than the specific UV agent, anti-fading agents, fillers, surfactants, polymerizable compounds, polymerization initiators, adhesion promoters, antioxidants, and anti-aggregation agents. Furthermore, the composition may further contain resins, solvents, and the like depending on the intended use of the composition.

[0141] (Dyes Other Than the Specific Dyes) The composition of the present disclosure may contain dyes (e.g., dyes and pigments) other than the specific dyes, as needed, depending on the application or purpose. Examples of dyes other than the specific dyes include phthalocyanine dyes, xanthene dyes, triarylmethane dyes, methine dyes, azo dyes, and anthraquinone dyes, 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. Dyes other than the specific dyes may or may not have a maximum absorption wavelength in the wavelength range of 450 nm to 500 nm.

[0142] As the dye other than the specific pigment, 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.

[0143] Examples of pigments other than the specific dye 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.

[0144] When the composition of the present disclosure contains a pigment other than 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 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 composition.

[0145] (Ultraviolet Absorber Other Than Specific UV Agent) The composition of the present disclosure may contain an ultraviolet absorber other than the above-mentioned specific UV agent (also referred to as other UV agent) as necessary. By including the specific UV agent, the composition of the present disclosure has a high effect of blocking or suppressing ultraviolet light of the composition, but by further including another UV agent having a maximum absorption wavelength different from the specific UV agent, for example, an effect of blocking or suppressing ultraviolet light of a wider range of wavelengths can be expected.

[0146] Examples of other UV agents include ultraviolet absorbing compounds selected from the group consisting of dibenzoylmethane compounds, cinnamic acid compounds, benzoic acid ester compounds, oxalic acid diamide compounds, and formamidine compounds. Other UV agents that can be used in the composition of the present disclosure are described, for example, in "Fine Chemical" (May 2004 issue), pages 28-38; "New Developments in Functional Additives for Polymers" (Toray Research Center, 1999), published by the Research and Development Division of Toray Research Center; "Development and Environmental Measures of Polymer Additives" edited by Yasukazu Ohkatsu (CMC Publishing, 2003), pages 54-64; and "Polymer Degradation and Discoloration Mechanisms and Their Stabilization Techniques - Collection of Know-How" (Technical Information Association, 2006), published by the Technical Information Association. Other UV agents can also be appropriately selected from the compounds described in these documents depending on the purpose.

[0147] When the composition of the present disclosure contains other UV agents, the other UV agents may be contained alone or in combination of two or more. When the composition of the present disclosure contains other UV agents in addition to the specific UV agent, the content of the ultraviolet absorber in the composition may be selected appropriately depending on the type of ultraviolet absorber, and generally can be 0.01% by mass to 20% by mass relative to the total mass of the composition. Note that when the composition contains both the specific UV agent and the other UV agent, the content of the specific UV agent relative to the total amount of the ultraviolet absorbers is preferably 50% by mass or more, and more preferably 80% by mass or more.

[0148] (Other Components) The composition of the present disclosure may contain components other than the above components (so-called other components). Examples of the other components include fillers, surfactants, polymerizable compounds, polymerization initiators, adhesion promoters, antioxidants, UV absorbers, and anti-aggregation agents. Regarding the polymerizable compounds and polymerization initiators, those usable in the liquid compositions described below can be used in the same way, and therefore further description here is omitted.

[0149] The composition of the present disclosure can be prepared by mixing the dye represented by Formula 1 (i.e., the specific dye), the specific UV agent, and other components used as needed.

[0150] <Resin Composition> The resin composition of the present disclosure contains a dye represented by the following formula 1, at least one ultraviolet absorber selected from the above compound group I, and a resin.

[0151]

[0152] In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent, R ５ and R ６ may be bonded to each other to form a 6-membered ring. The dye represented by Formula 1 contained in the resin composition according to the second aspect of the present disclosure (hereinafter also referred to as the resin composition according to the present disclosure) is the same as the specific dye in the composition according to the present disclosure described above, and preferred examples are also the same.

[0153] The at least one ultraviolet absorber selected from the compound group I contained in the resin composition of the present disclosure is the same as the specific UV agent described above, and preferred examples are also the same.

[0154] The resin composition of the present disclosure can be molded into any shape by containing a resin. The resin composition of the present disclosure can be molded by a known molding method to obtain a resin molded product that has good ultraviolet blocking properties, high absorbance for light with wavelengths of at least 350 nm to 450 nm, and excellent light resistance and heat resistance. Specifically, it can be used to obtain materials that block or suppress ultraviolet (UV) and blue light (e.g., molded products such as glass, films, sheets, and lenses).

[0155] (Resin) The resin composition of the present disclosure contains 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.

[0156] 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.

[0157] 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.

[0158] Examples of ester resins include polymers obtained by reacting polyols (e.g., ethylene glycol, propylene glycol, glycerin, and trimethylolpropane) with polybasic acids (e.g., aromatic dicarboxylic acids (e.g., terephthalic acid, isophthalic acid, and naphthalenedicarboxylic acid, and dicarboxylic acids in which hydrogen atoms on these aromatic rings are substituted with methyl groups, ethyl groups, or phenyl groups), aliphatic dicarboxylic acids having 2 to 20 carbon atoms (e.g., adipic acid, sebacic acid, and 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).

[0159] Examples of epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, phenol novolac type epoxy resins, cresol novolac type epoxy resins, aliphatic epoxy resins, etc. As the epoxy resin, commercially available products on the market may be used, and examples of commercially available products include the following:

[0160] Examples of commercially available bisphenol A 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). Commercially available examples of bisphenol F 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.). Commercially available examples of phenol novolac epoxy resins include jER152, jER154, jER157S70, and jER157S65 (all manufactured by Mitsubishi Chemical Corporation), and EPICLON N-740, EPICLON N-770, and EPICLON N-775 (all manufactured by DIC Corporation). Commercially available 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.).Commercially available 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 (manufactured by Daicel Corporation), DENACOL EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (manufactured by Nagase ChemteX Corporation), ADEKA RESIN Examples of such a resin include the EP series (e.g., EP-4000S, EP-4003S, EP-4010S, and EP-4011S; manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, and EPPN-502 (all manufactured by ADEKA Corporation), and jER1031S (manufactured by Mitsubishi Chemical Corporation). Other commercially available 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 (all manufactured by NOF Corporation, epoxy group-containing polymers).

[0161] The resin may have an acid group. Examples of the acid group include a carboxy group, a phosphate 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.

[0162] 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.

[0163] 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 other monomers copolymerizable with (meth)acrylic acid, N-substituted maleimide monomers (e.g., N-phenylmaleimide and N-cyclohexylmaleimide) 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, and polymethyl methacrylate macromonomer. The other monomers copolymerizable with (meth)acrylic acid may be one type or two or more types.

[0164] 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, a 2-hydroxyethyl (meth)acrylate polymer, 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.

[0165] For examples of resins having an acid group, 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, as a resin having an acid group, ACRYBASE FF-426 (manufactured by Nippon Shokubai Co., Ltd.) can also be used.

[0166] 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 more preferably 50 mgKOH / g or more, and even more preferably 70 mgKOH / g or more. The upper limit of the acid value is more preferably 150 mgKOH / g or less, and even 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.

[0167] The resin may have a curable group. The resin is preferably a copolymer containing a structural unit having a curable group. Examples of the curable 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.

[0168] Examples of the structural unit having a curable group include structural units represented by the following formulas (A2-1) to (A2-4).

[0169]

[0170] 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.

[0171] 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 -, -NR-, or a combination of two or more of these. Here, R represents a hydrogen atom or an alkyl group, and a hydrogen atom is preferred. ５１ The divalent linking group in is preferably a group formed by combining at least one selected from an alkylene group and an arylene group with —O—. ５１ The number of carbon atoms in the alkylene group in the formula (I) 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, but is preferably unsubstituted. The alkylene group may be linear, branched, or cyclic. Furthermore, the cyclic alkylene group may be monocyclic or polycyclic. L ５１The 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.

[0172] Y １ represents a curable group. Examples of the curable 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, the epoxy group, the methylol group, and the alkoxysilyl group are as described above.

[0173] The resin containing a curable group may be a commercially available product on the market. Examples of commercially available resins containing a curable group include the DIANAL BR series (polymethyl methacrylate (PMMA), for example, DIANAL BR-80, BR-83, and BR-87; manufactured by Mitsubishi Chemical Corporation), Photomer 6173 (a COOH-containing polyurethane acrylic oligomer; manufactured by Diamond Shamrock Co., Ltd.), Viscoat R-264, and KS Resist 106 (all manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series (for example, ACA230AA), Plaxel CF200 series (all manufactured by Daicel Corporation), and Ebecryl 3800 (manufactured by Daicel-UCB Corporation), and Acrylicure RD-F8 (manufactured by Nippon Shokubai Co., Ltd.). Other examples include commercially available epoxy resins such as those mentioned above.

[0174] For example, when the resin composition of the present disclosure is used for lenses (e.g., eyeglass lenses), suitable resins are thermoplastic resins such as carbonate resins and (meth)acrylic resins (e.g., polymethyl methacrylate (PMMA)), and thermosetting resins such as urethane resins. Commercially available examples of carbonate resins include polycarbonate resin composition (trade name: Caliber 200-13, manufactured by Sumitomo Dow Co., Ltd.) and diethylene glycol bisallyl carbonate resin (trade name: CR-39, manufactured by PPG Industries). Thiourethane resins are preferred as urethane resins. Commercially available examples of raw materials for thiourethane resins include thiourethane resin monomers (trade names: MR-7, MR-8, MR-10, and MR-174, manufactured by Mitsui Chemicals, Inc.).

[0175] The weight average molecular weight (Mw) of the resin is preferably 2,000 to 2,000,000. The lower limit of the Mw of the resin is more preferably 5,000 or more, even more preferably 10,000 or more, and particularly preferably 50,000 or more. The upper limit of the Mw of the resin is more preferably 1,000,000 or less, even more preferably 500,000 or less, and particularly preferably 200,000 or less. Furthermore, when an epoxy resin is used, the weight average molecular weight (Mw) of the epoxy resin is preferably 100 or more, more preferably 200 to 2,000,000. The upper limit of the Mw of the epoxy resin is more preferably 1,000,000 or less, and particularly preferably 500,000 or less. The lower limit of the Mw of the epoxy resin is more preferably 2,000 or more.

[0176] 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 (manufactured by Tosoh Corporation) as a measuring device, three TSKgel (registered trademark) Super Multipore HZ-H columns (4.6 mm ID x 15 cm, manufactured by 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".

[0177] The resin composition of the present disclosure may contain one type of resin alone or two or more types. The content of the resin in the resin composition of the present disclosure 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 of the present disclosure is within the above range, the moldability during molding is improved.

[0178] Similar to the compositions of the present disclosure described above, the resin composition of the present disclosure may further contain, in addition to the specific dye and the specific UV agent, dyes other than the specific dye, other UV agents, and known additives that are typically used in resin compositions, depending on the purpose.

[0179] <Liquid Composition> The liquid composition of the present disclosure contains a dye represented by Formula 1 (i.e., a specific dye), a specific UV agent, and a solvent. Because the liquid composition of the present disclosure contains the specific dye and the specific UV agent, it has excellent shielding properties in at least the wavelength region of 350 nm to 450 nm, excellent light resistance and heat resistance, and is inhibited from aggregating over time of the specific dye and the specific UV agent, resulting in excellent stability.

[0180] The resin composition of the present disclosure may further contain other dyes than the specific dye, other UV agents, and other components as necessary. Details of the other dyes than the specific dye, other UV agents, and other components are the same as those in the composition of the present disclosure described above, and therefore will not be described here.

[0181] (Dye) The dye represented by formula 1 (i.e., specific dye) contained in the liquid composition of the present disclosure has the same definition as the specific dye in the composition of the present disclosure described above, and preferred embodiments are also the same.

[0182] The liquid composition of the present disclosure may contain one type of dye (specific dye) represented by Formula 1 alone, or may contain two or more types. The content of the dye (specific dye) represented by Formula 1 in the liquid composition of the present disclosure is preferably 0.01% by mass to 20% by mass, and more preferably 0.1% by mass to 5% by mass, relative to the total solid content of the liquid composition. The dye (specific dye) represented by Formula 1 has high absorbance particularly in the wavelength region of 350 nm to 450 nm, and therefore, when the content of the specific dye in the liquid composition of the present disclosure is within the above range, the liquid composition of the present disclosure becomes a liquid composition with excellent function of blocking or suppressing light with wavelengths of 350 nm to 450 nm.

[0183] (Solvent) The liquid composition of the present disclosure contains at least one solvent, such as water, an organic solvent, or a mixed solvent of water and an organic solvent.

[0184] As the water, distilled water, ion-exchanged water, etc. can be used. The organic solvent can be appropriately selected depending on the use or purpose of the liquid composition. Examples of the organic solvent include esters, ethers, ketones, aromatic hydrocarbons, etc.

[0185] Examples of the ester 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.)), alkyl 2-oxypropionate solvents (e.g., 2-oxypropionate, alkyl 3-oxypropionate, alkyl 4-oxypropionate, alkyl 5-oxypropionate, alkyl 6-oxypropionate, alkyl 7-oxypropionate, alkyl 8-oxypropionate, alkyl 9-oxypropionate, alkyl 10-oxypropionate, alkyl 11-oxypropionate, alkyl 12-oxypropionate, alkyl 13-oxypropionate, alkyl 14-oxypropionate, alkyl 15-oxypropionate, alkyl 16-oxypropionate, alkyl 17-oxypropionate, alkyl 18-oxypropionate, alkyl 19-oxypropionate, alkyl 20-oxypropionate, alkyl 21-oxypropionate, alkyl 22-oxypropionate, alkyl 23-oxypropionate, alkyl 24-oxypropionate, alkyl 25-oxypropionate, alkyl 26-oxypropionate, alkyl 27-oxypropionate, alkyl 28-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.

[0186] 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.

[0187] Ketones include, for example, methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone.

[0188] Suitable examples of aromatic hydrocarbons include toluene and xylene.

[0189] The liquid composition of the present disclosure may contain one organic solvent alone, or may contain two or more organic solvents from the viewpoint of application or improvement of the solubility of each component or the coated surface condition. When the liquid composition of the present disclosure contains two or more organic solvents, it is preferable that the organic solvents contain 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.

[0190] The content of the solvent in the liquid composition of the present disclosure is preferably an amount such that the total solid content in the liquid composition is 10% by mass to 80% by mass, and more preferably 15% by mass to 60% by mass.

[0191] When the liquid composition of the present disclosure contains a curable component, it can be used as a composition having curability (so-called curable composition). The curable composition is a composition that can be cured by the application of energy. The curable composition is preferably a composition that exhibits curability by the application of energy such as irradiation with visible light, ultraviolet light (UV), electron beams, or heating. Among these, as the curable composition, a composition that exhibits curability by irradiation with ultraviolet light is more preferred from the viewpoints of versatility and good curing sensitivity.

[0192] (Polymerizable Compound) The liquid composition of the present disclosure can be prepared as a curable composition by further containing a polymerizable compound in addition to the components described above. As the polymerizable compound, any compound that can be polymerized and cured upon application of energy can be used without limitation.

[0193] The polymerizable compound may be, for example, an addition-polymerizable compound having at least one ethylenically unsaturated double bond. The addition-polymerizable compound may be selected from compounds having at least one terminal ethylenically unsaturated bond, and preferably a compound having two or more terminal ethylenically unsaturated bonds.

[0194] The polymerizable compound may be, for example, any of a monomer, a prepolymer (i.e., a dimer, trimer, or oligomer), a mixture thereof, and a polymer of a compound selected from a monomer and a prepolymer.

[0195] Examples of the polymerizable compound include unsaturated carboxylic acids (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, and maleic acid), esters of unsaturated carboxylic acids, amides of unsaturated carboxylic acids, and polymers of unsaturated carboxylic acids or their esters or amides. Among these, preferred polymerizable compounds are esters of unsaturated carboxylic acids and aliphatic polyhydric alcohols, amides of unsaturated carboxylic acids and aliphatic polyamines, and homopolymers or copolymers thereof.

[0196] Examples of the polymerizable compound include an addition reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a nucleophilic substituent (e.g., a hydroxy group, an amino group, or a mercapto group) with a monofunctional or polyfunctional isocyanate compound or an epoxy compound; a dehydration condensation reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a nucleophilic substituent with a monofunctional or polyfunctional carboxylic acid; an addition reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having an electrophilic substituent (e.g., an isocyanate group or an epoxy group) with a monofunctional or polyfunctional alcohol, amine, or thiol; and a substitution reaction product of an unsaturated carboxylic acid ester or unsaturated carboxylic acid amide having a leaving substituent (e.g., a halogen group or a tosyloxy group) with a monofunctional or polyfunctional alcohol, amine, or thiol. Further examples of the polymerizable compound include compounds obtained by substituting the above-mentioned unsaturated carboxylic acid with an unsaturated phosphonic acid, styrene, or vinyl ether.

[0197] When the liquid composition of the present disclosure contains a polymerizable compound, the details of the polymerizable compound, such as the structure, the selection of the use of a single compound or a combination of two or more compounds, and the content, may be arbitrarily set according to the use or purpose of the liquid composition. For example, from the viewpoint of the curing sensitivity of the liquid composition, the polymerizable compound is preferably a compound having a high content of a group having an ethylenically unsaturated double bond (also referred to as an unsaturated group) per molecule, and more preferably a bifunctional or higher functional compound having two or more unsaturated groups. Furthermore, for example, from the viewpoint of increasing the strength of a resin layer formed by applying the liquid composition, the polymerizable compound is preferably a trifunctional or higher functional compound having three or more unsaturated groups, for example, a hexafunctional acrylate compound.

[0198] Furthermore, the liquid composition of the present disclosure may contain a combination of multiple compounds with different functionalities or multiple compounds with different types of polymerizable groups (e.g., acrylic acid esters, methacrylic acid esters, styrene-based compounds, and vinyl ether-based compounds) as the polymerizable compound. By using a combination of multiple polymerizable compounds, it is possible to adjust both sensitivity and strength.

[0199] The polymerizable compound may be a commercially available product. Examples of commercially available polymerizable compounds include KYARAD (registered trademark) PET-30 and KYARAD (registered trademark) TPA-330 manufactured by Nippon Kayaku Co., Ltd., POLYVEST (registered trademark) 110M manufactured by Evonik, and polyfunctional acrylate A-9300 (trade name) manufactured by Shin-Nakamura Chemical Co., Ltd.

[0200] When the liquid composition of the present disclosure contains a polymerizable compound, it may contain one type of polymerizable compound alone or two or more types of polymerizable compounds. There are no particular restrictions on the content of the polymerizable compound in the liquid composition of the present disclosure. When the liquid composition of the present disclosure contains a polymerizable compound, the content of the polymerizable compound in the liquid composition is preferably 30% by mass to 99.5% by mass, more preferably 50% by mass to 99% by mass, and even more preferably 60% by mass to 98% by mass, based on the total solid content of the liquid composition.

[0201] The liquid composition of the present disclosure may also use a polymer compound as the polymerizable compound. Examples of the polymerizable compound include (meth)acrylic resins, ester resins, urethane resins, and fluorine-based resins. As the polymerizable compound, commercially available products may be used. Examples of commercially available polymerizable compounds include the Dianal BR series (polymethyl methacrylate (PMMA), for example, Dianal BR-80, BR-83, and BR-87; manufactured by Mitsubishi Chemical Corporation), Photomer 6173 (a COOH-containing polyurethane acrylic oligomer, Diamond Shamrock Co., Ltd.), Viscoat R-264, and KS Resist 106 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Cyclomer P series (for example, ACA230AA), and Plaxel CF200 series (manufactured by Daicel Corporation), Ebecryl 3800 (manufactured by Daicel-UCB Co., Ltd.), and Acrylicure RD-F8 (manufactured by Nippon Shokubai Co., Ltd.). When the liquid composition of the present disclosure contains a polymerizable compound having a high molecular weight, the liquid composition may contain one type of polymerizable compound alone or two or more types of polymerizable compounds, but from the viewpoint of film uniformity, it is preferable that the liquid composition contain one type of polymerizable compound alone.

[0202] From the viewpoint of improving the strength after curing, the polymerizable compound of high molecular weight is preferably a compound capable of forming a crosslinked structure. The method of forming the crosslinked structure is not particularly limited, and examples thereof include a method of using a polymerizable compound of high molecular weight and a polyfunctional (meth)acrylate monomer having an unsaturated group capable of addition polymerization with the unsaturated group of the polymerizable compound of high molecular weight in combination, or a method of using a polymerizable compound of high molecular weight (e.g., a (meth)acrylic resin) having a reactive group (e.g., a hydroxyl group) introduced therein in combination with a crosslinking agent having a crosslinkable group capable of reacting with the reactive group.

[0203] Examples of reactive groups include groups containing active hydrogen, and specific examples include groups selected from the group consisting of hydroxyl groups, primary amino groups, and secondary amino groups. Examples of polymerizable compounds having reactive groups introduced therein include (meth)acrylic resins containing structural units derived from (meth)acrylate monomers and having two or more groups containing active hydrogen. Examples of crosslinking agents include polyisocyanates having two or more isocyanate groups as crosslinkable groups. Commercially available crosslinking agents may also be used. Examples of commercially available crosslinking agents include AD-TMP and A-9550 (both trade names) from Shin-Nakamura Chemical Co., Ltd. Among these, a preferred method for forming a crosslinked structure is a method in which a (meth)acrylic resin having two or more (preferably three or more) active hydrogen-containing groups is used in combination with a crosslinking agent having two or more isocyanate groups (preferably a polyisocyanate having two or more isocyanate groups, more preferably a polyisocyanate having three or more isocyanate groups). In this method, a crosslinked structure can be formed by reacting an active hydrogen-containing group with an isocyanate group. This method is preferable from the viewpoint of increasing the crosslink density in the formed resin body (e.g., resin layer) and further improving the strength of the resin body.

[0204] When the liquid composition of the present disclosure contains a polymerizable compound, the content of the polymerizable compound in the liquid composition is preferably 30% by mass to 99.5% by mass, more preferably 50% by mass to 99% by mass, and even more preferably 60% by mass to 98% by mass, relative to the total solid content of the liquid composition. Furthermore, when a polymerizable compound having a reactive group introduced therein is used in combination with a crosslinking agent, the content of the crosslinking agent in the liquid composition is preferably 5 parts by mass to 80 parts by mass, more preferably 10 parts by mass to 50 parts by mass, relative to 100 parts by mass of the polymerizable compound.

[0205] (Polymerization initiator) The liquid composition of the present disclosure may further contain a polymerization initiator in addition to the components described above. When the liquid composition of the present disclosure further contains a polymerization initiator, the polymerization reaction of the polymerizable compound 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.

[0206] The photopolymerization initiator is preferably, for example, a compound that absorbs light in the ultraviolet to visible light range (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.

[0207] 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.

[0208] 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).

[0209] As the photopolymerization initiator, an oxime-based 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).

[0210] 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.

[0211] 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.

[0212] When the liquid composition of the present disclosure contains a polymerization initiator, it may contain one type of polymerization initiator alone or two or more types. When the liquid composition of the present disclosure contains a polymerization initiator, the content of the polymerization initiator in the liquid composition is preferably 0.1% by mass to 20% by mass, more preferably 0.3% by mass to 15% by mass, and even more preferably 0.4% by mass to 10% by mass, relative to the total solid content of the liquid composition.

[0213] The liquid composition of the present disclosure can be prepared by mixing the dye represented by Formula 1 (i.e., the specific dye), the specific UV agent and the solvent, and, as necessary, a polymerizable compound, a polymerization initiator, an ultraviolet absorber, and other components.

[0214] The composition of the present disclosure, the resin composition of the present disclosure, and the liquid composition of the present disclosure may further contain at least one anti-fading agent selected from the group consisting of amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds, carotenoid compounds, metal complex compounds, and benzolactone compounds.

[0215] The amine compound is preferably a hydroxyamine compound, a tertiary amine compound, or an aminooxyl compound, more preferably a tertiary amine compound or an aminooxyl compound. The metal complex compound is preferably a Ni complex compound or a Co complex compound, more preferably a Ni complex compound. The anti-fading agent is preferably at least one selected from an amine compound and a benzolactone compound, more preferably an amine compound.

[0216] When the composition of the present disclosure, the resin composition of the present disclosure, and the liquid composition of the present disclosure further contain an anti-fading agent, the light resistance of the specific dye is further improved, and further, the light resistance of the specific UV agent is further improved.

[0217] The above-mentioned anti-fading agent preferably contains at least one compound selected from the group consisting of compounds represented by the following formula (3-1) and formula (3-2), and more preferably contains a compound represented by the following formula (3-1).

[0218]

[0219] In formula (3-1), R ａ１ , R ａ２ , R ａ３ and R ａ４ each independently represents a hydrogen atom, an alkyl group, or an alkenyl group; ａ１represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group or an oxy radical group; X ａ２ represents the atomic group necessary to form a 5- to 7-membered ring.

[0220] In formula (3-2), R ｐ１ represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or —Si(R ｐ１０１ ) (Rp １０２ ) (Rp １０３ ) and R ｐ１０１ , Rp １０２ and Rp １０３ each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, or an aryloxy group; R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ each independently represents a hydrogen atom or a substituent, ｐ１ , R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ two adjacent groups among R may be bonded to form a ring; ｐ１ , R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ cannot all be hydrogen atoms.

[0221] The above groups in formula (3-1) and formula (3-2) may further have a substituent, which may be any of the substituents included in the above-mentioned substituent group A.

[0222] -Compound represented by formula (3-1)- R in formula (3-1) ａ１ ~R ａ４ are each independently preferably an alkyl group or an alkenyl group, more preferably an alkyl group. The alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms. The alkyl group may be linear, branched, or cyclic, but is preferably linear. The alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T. The alkenyl group preferably has 2 to 5 carbon atoms, more preferably 2 or 3 carbon atoms. The alkenyl group is preferably linear or branched, more preferably linear. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0223] R ａ１ ~R ａ４ is particularly preferably a methyl group.

[0224] X in formula (3-1) ａ１is preferably a hydrogen atom, an oxy radical group, an alkyl group, an alkoxy group, an alkenyl group, an acyl group, or an aryl group, and more preferably an oxy radical group or an alkoxy group. The alkyl group preferably has 1 to 20 carbon atoms, and more preferably 1 to 12 carbon atoms. The alkyl group may be linear, branched, or cyclic, but is preferably linear. The alkyl group may have a substituent. Examples of the substituent include the groups listed above for substituent T. The alkenyl group preferably has 2 to 20 carbon atoms, and more preferably 2 to 12 carbon atoms. The alkenyl group is preferably linear or branched, and more preferably linear. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for substituent T. The alkoxy group preferably has 1 to 20 carbon atoms, and more preferably 1 to 12 carbon atoms. The alkoxy group is preferably linear or branched, and more preferably linear. The alkoxy may have a substituent. Examples of the substituent include the groups listed above for substituent T. The acyl group preferably has 2 to 20 carbon atoms, and more preferably 2 to 14 carbon atoms. The acyl group may have a substituent. Examples of the substituent include the groups exemplified above for the substituent T. The number of carbon atoms in the aryl group is preferably 6 to 20. The aryl group may have a substituent. Examples of the substituent include the groups exemplified above for the substituent T.

[0225] The compound represented by formula (3-1) is preferably a compound represented by formula (3-1-2).

[0226]

[0227] In formula (3-1-2), X ａ１１represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group, or an oxy radical group; R ａ１１ represents a substituent;

[0228] X in formula (3-1-2) ａ１１ is X in formula (3-1). ａ１ The same applies to the preferred range.

[0229] R in formula (3-1-2) ａ１１ Examples of the substituent represented by include the groups exemplified above as the substituent T. Examples of the alkyl group include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group.

[0230] The compound represented by formula (3-1) is preferably a compound represented by formula (3-1-3).

[0231]

[0232] In formula (3-1-3), X ａ２１ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group or an oxy radical group; L ａ２１ represents a single bond or a divalent linking group; ａ２２ represents an n-valent group, and n represents an integer of 1 or more.

[0233] X in formula (3-1-3) ａ２１ is X in formula (3-1). ａ１ The same applies to the preferred range.

[0234] L in formula (3-1-3) ａ２１ The divalent linking group represented by the formula (I) includes -O-, -CO-, -COO-, -OCO-, -NHCO-, -NHCOO-, -CONH-, -OCONH-, -S-, and -SO ２ --and--OSO ２ - are listed.

[0235] L in formula (3-1-3) ａ２２ represents an n-valent group. ａ２２ When the n-valent group represented by is a monovalent group (when n is 1), L ａ２２Examples of the n-valent group represented by the formula (I) include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl Examples of the alkyl group include an arylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group.

[0236] L ａ２２ When the n-valent group represented by is a divalent or higher valent group (when n is an integer of 2 or more), L ａ２２ Examples of the n-valent group represented by include hydrocarbon groups; and groups in which two or more hydrocarbon groups are bonded via -O-, -CO-, -COO-, -OCO-, -NH-, -S-, or a group combining two or more of these. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups, with aliphatic hydrocarbon groups being preferred. 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, with linear or branched being preferred. The aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, with saturated aliphatic hydrocarbon groups being preferred. 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 a halogen atom, a hydroxy group, an alkyl group, and an aryl group.

[0237] When the n-valent group is a divalent or higher valent group, Lａ２２ The n-valent linking group represented by is preferably a group containing a saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms (preferably 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms).

[0238] In formula (3-1-3), n represents an integer of 1 or more, preferably an integer of 2 or more, more preferably an integer of 2 to 6, and even more preferably an integer of 2 to 4.

[0239] -Compound represented by formula (3-2)- R in formula (3-2) ｐ１ represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or —Si(R ｐ１０１ ) (R ｐ１０２ ) (R ｐ１０３ ) and R ｐ１０１ ~R ｐ１０３ R each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, or an aryloxy group. ｐ１ is preferably a hydrogen atom, an alkyl group or an acyl group, more preferably an alkyl group or an acyl group.

[0240] R ｐ２ ~R ｐ６Examples of the substituent represented by the formula (I) include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfamoyl group, a sulfonylamino ... Examples of the alkyl group include a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group. The alkyl group is preferably an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkoxycarbonyl group, an aryloxy group, an aryloxycarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group, more preferably an alkyl group or an alkenyl group, and even more preferably an alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably branched. The alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T. The alkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 5 carbon atoms. The alkenyl group is preferably linear or branched, and more preferably branched. The alkenyl group may have a substituent. Examples of the substituent include the groups exemplified above for the substituent T.

[0241] In formula (3-2), R ｐ２ ~R ｐ６ At least one of the groups is preferably a substituent, and two or more of the groups are more preferably substituents.

[0242] In formula (3-2), Rｐ１ ~R ｐ６ Among these, two adjacent groups may be bonded to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed may further have a substituent. Examples of the substituent include the groups exemplified above for the substituent T and ethylenically unsaturated bond-containing groups. Examples of the ethylenically unsaturated bond-containing group include a vinyl group.

[0243] As a preferred embodiment of formula (3-2), R ｐ１ and R ｐ２ and bonded to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed preferably further has a substituent. Examples of the substituent include an aryl group, a heteroaryl group, and an ethylenically unsaturated bond-containing group, preferably an aryl group or an ethylenically unsaturated bond-containing group, and more preferably an aryl group. The aryl group and the heteroaryl group may further have a substituent. Examples of the further substituent include an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an acyl group, and a hydroxy group.

[0244] In formula (3-2), R ｐ１ ~R ｐ６ Not all of R are hydrogen atoms. ｐ１ ~R ｐ６ The total number of carbon atoms is preferably 10 or more, and more preferably 16 or more.

[0245] The compound represented by formula (3-2) is preferably a compound represented by formula (3-2-2).

[0246]

[0247] In formula (3-2-2), R ｐ１１ ~R ｐ１４ each independently represents a hydrogen atom, an alkyl group, or an alkenyl group; Y ｐ１１ represents an aryl group, a heteroaryl group, or an ethylenically unsaturated bond-containing group.

[0248] R ｐ１１ ~R ｐ１４The number of carbon atoms in the alkyl group represented by is preferably 1 to 10, more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, more preferably branched. The alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T. R ｐ１１ ~R ｐ１４ The number of carbon atoms in the alkenyl group represented by is preferably 2 to 10, and more preferably 2 to 5. The alkenyl group is preferably linear or branched, and more preferably branched. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.

[0249] R ｐ１１ ~R ｐ１４ It is preferable that at least one of R is an alkyl group or an alkenyl group, and it is more preferable that two or more of R are alkyl groups or alkenyl groups. ｐ１１ ~R ｐ１４ At least one of the groups is preferably an alkyl group, and more preferably two or more of the groups are alkyl groups.

[0250] Y ｐ１１ represents an aryl group, a heteroaryl group, or an ethylenically unsaturated bond-containing group, and is preferably an aryl group. The aryl group and heteroaryl group may further have a substituent. Examples of the further substituent include an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, an aryloxy group, an acyl group, and a hydroxy group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group.

[0251] The compound represented by formula (3-2) is preferably a compound represented by formula (3-2-3).

[0252]

[0253] In formula (3-2-3), R ｐ２１ ~R ｐ２４ each independently represents a hydrogen atom, an alkyl group, or an alkenyl group; R ｐ２５ represents an alkyl group, an alkenyl group, or a hydroxy group; L ｐ２１represents an s-valent group, r represents an integer of 0 to 4, s represents an integer of 1 or more, and when r is an integer of 2 or more, there are r R ｐ２５ may be the same or different.

[0254] R in formula (3-2-3) ｐ２１ ~R ｐ２４ is R in formula (3-2-2). ｐ１１ ~R ｐ１４ The same definition and preferred range are also true. ｐ２１ ~R ｐ２４ It is preferable that at least one of R is an alkyl group or an alkenyl group, and it is more preferable that two or more of R are alkyl groups or alkenyl groups. ｐ２１ ~R ｐ２４ At least one of the groups is preferably an alkyl group, and more preferably two or more of the groups are alkyl groups.

[0255] R in formula (3-2-3) ｐ２５ is preferably an alkyl group or an alkenyl group, more preferably an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, more preferably branched. The alkyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T. The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 5. The alkenyl group is preferably linear or branched, more preferably branched. The alkenyl group may have a substituent. Examples of the substituent include the groups listed above for the substituent T. ｐ２１ represents an s-valent group. ｐ２１ When the s-valent group represented by is a monovalent group, L ｐ２１ The s-valent group represented by L includes an alkyl group, an alkenyl group, an alkoxy group, and an alkynyl group, and is preferably an alkyl group or an alkoxy group. ｐ２１ When the s-valent group represented by is a divalent or higher valent group, L ｐ２１The s-value represented by the formula (I) is a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NHCO-, -NHCOO-, -CONH-, -OCONH-, -S-, -SO ２ --OSO ２ - and groups combining two or more of these groups. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. 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, but is preferably linear or branched. The aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, but is preferably a saturated aliphatic hydrocarbon group. 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 a halogen atom, a hydroxy group, an alkyl group, and an aryl group.

[0256] r represents an integer of 0 to 4, and preferably an integer of 0 to 2. s represents an integer of 1 or more, and preferably an integer of 1 to 4, and more preferably 1 or 2.

[0257] Specific examples of the anti-fading agent include the compounds described in the examples below, the compounds described in paragraphs 0157 to 0171 of JP-A-2009-067984, and compounds having the structures shown below.

[0258]

[0259]

[0260]

[0261] When the composition, resin composition, and liquid composition of the present disclosure contain an anti-fading agent, the content of the anti-fading agent is preferably 0.01 to 50 mass% relative to the total solids content of the composition. The lower limit is preferably 0.05 mass% or more, and more preferably 0.1 mass% or more. The upper limit is preferably 40 mass% or less, more preferably 30 mass% or less, and even more preferably 20 mass% or less. The composition, resin composition, and liquid composition of the present disclosure may contain only one type of anti-fading agent, or may contain two or more types. When two or more types of anti-fading agents are contained, the total amount thereof is preferably within the above range.

[0262] In particular, from the viewpoint of further improving the lightfastness of the specific dye, the content ratio of the specific dye to the anti-fading agent is preferably in the range of 1:20 to 20:1 by mass, more preferably in the range of 1:10 to 10:1, and even more preferably in the range of 1:5 to 5:1. When the content ratio of the specific dye to the anti-fading agent is in the above range, precipitation of the specific dye and the specific UV agent is effectively suppressed, and the effect of improving the lightfastness of the composition by adding the anti-fading agent is sufficiently obtained.

[0263] <Dye Compound> A first aspect of the dye compound of the present disclosure is a dye compound represented by the following formula 4. The dye compounds represented by formula 4 are included in the dyes represented by formula 1, but compounds within the range represented by formula 4 are novel dye compounds.

[0264]

[0265] In formula 4, R ４１ represents a hydrogen atom, an alkyl group, or an aryl group. ４１ When represents a hydrogen atom, R ４２ represents a secondary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, a tertiary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, or an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms; R ４１ represents an alkyl group or an aryl group, R ４２ represents a hydrogen atom or a substituent. ４３ , R ４４, R ４５ and R ４６ R each independently represents a hydrogen atom or a substituent. ４１ ~R ４６ When represents a substituent, examples of the substituent include the substituents included in the above-mentioned substituent group A.

[0266] R in Equation 4 ４１ The alkyl group or aryl group in the formula 1 is １ The meanings and preferred embodiments are the same as those of the alkyl group or aryl group in the above formula (I).

[0267] R ４１ is preferably a hydrogen atom, a methyl group, or a phenyl group. ４１ When R is a hydrogen atom, the absorption of the dye compound in the long wavelength region becomes sharper, and when R is a methyl group, the light resistance of the dye compound is further improved. ４１ is a hydrogen atom, R ４２ is preferably a secondary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, a tertiary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, or an alkyl group having an electron-withdrawing group. ４２ When the carbon atom directly bonded to the nitrogen atom is a branched secondary alkyl group, the dye compound has sharper absorption in the long wavelength region, and when the alkyl group has an electron-withdrawing group, the dye compound has improved light resistance. ４２ In another preferred embodiment, the carbon atom adjacent to the nitrogen atom is an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms. When the carbon atom adjacent to the nitrogen atom is an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms, the crystallization properties of the synthetic intermediate are improved, and purification efficiency is improved, resulting in an improved yield, compared to a primary alkyl group in which the carbon atom adjacent to the nitrogen atom has a substituent, or a substituent in which a carbon atom further from the nitrogen atom than the carbon atom adjacent to the nitrogen atom has a branch, for example, a substituent in which a carbon atom having 8 carbon atoms has a branch and is further from the nitrogen atom. ４３ ~R ４６From the viewpoint of making the absorption of the dye compound in the long wavelength region sharper, R is preferably a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, an amino group, or an alkylamino group. ４３ ~R ４６ is also preferably an electron-withdrawing group from the viewpoint of improving the light resistance of the dye compound, and is preferably a halogen atom, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group.

[0268] The compound represented by formula 4 is a compound represented by formula 1 １ and R ２ is a benzyl group. １ and R ２ The compound represented by formula 4 in which R is a benzyl group is １ and R ２ However, compared to a structure that is, for example, a phenyl group, the mobility of the bulky ring structure is good, and therefore, interactions between the coexisting dye compounds and between the dye compounds and the specific UV agent are inhibited, and aggregation caused by the interactions is suppressed, which is thought to suppress changes over time due to precipitation, aggregation, etc.

[0269] Specific examples of the dye compound represented by the above formula 4 include compounds included in the range represented by formula 4, among the compounds given above as specific examples of the dye represented by formula 1. However, in the present disclosure, the dye compound represented by formula 4 is not limited to the compounds shown as specific examples.

[0270] <Dye Compound> A second aspect of the dye compound of the present disclosure is a dye compound represented by the following formula 5. The dye compounds represented by formula 5 are included in the dyes represented by formula 1, but compounds within the range represented by formula 5 are novel dye compounds.

[0271]

[0272] In formula 5, R ５１ represents a hydrogen atom, a methyl group, or a phenyl group. ５１ When represents a hydrogen atom, R５２ represents a secondary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, a tertiary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, or an unsubstituted primary alkyl group having 1 to 6 carbon atoms; R ５１ represents a methyl group or a phenyl group, R ５２ represents a hydrogen atom or a substituent. ５３ , R ５４ , R ５５ and R ５６ Each independently represents a hydrogen atom or a substituent. ５１ When represents a hydrogen atom, R ５２ represents a secondary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, a tertiary alkyl group in which the carbon atom directly bonded to the nitrogen atom is branched, or an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms. ５２ It is believed that the R in Formula 5 has the advantage of improving the crystallization properties of the synthetic intermediate and improving the purification efficiency, thereby improving the yield, compared to when the carbon atom adjacent to the nitrogen atom is an unsubstituted primary alkyl group having 8 or more carbon atoms. ５３ , R ５４ , R ５５ and R ５６ is R in Equation 4 ４３ , R ４４ , R ４５ and R ４６ The same applies to the above, and preferred examples are also the same.

[0273] Specific examples of the dye compound represented by Formula 5 above include compounds that fall within the scope of Formula 5 among the compounds listed above as specific examples of the dye represented by Formula 1. However, in the present disclosure, the dye compound represented by Formula 5 is not limited to the specific examples. The dye compound represented by Formula 4 or Formula 5 can be synthesized by known methods. For example, reference can be made to paragraphs

[0073] to

[0078] of WO 2020 / 20291. Examples of synthesis methods include a method in which 1,2-dibenzylpyrazolidine-3,5-dione and indole-3-carboxaldehyde are mixed in an organic solvent at room temperature (25°C) or under reflux conditions.

[0274] <Optical Material> The optical material of the present disclosure is a cured product of the composition, resin composition, or liquid composition of the present disclosure. In another aspect of the optical material of the present disclosure, the optical material of the present disclosure contains at least one selected from the dye compound represented by Formula 4 of the present disclosure and the dye compound represented by Formula 5 of the present disclosure. Therefore, the optical material of the present disclosure contains at least the dye represented by Formula 1 of the present disclosure (i.e., the specific dye). Therefore, the optical material of the present disclosure has excellent shielding properties in the wavelength region of 350 nm to 450 nm, and is excellent in light resistance and heat resistance.

[0275] The term "cured product" in the present disclosure 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.

[0276] Examples of optical materials include optical filters (e.g., optical lenses), and optical films or optical sheets (e.g., films for vehicle or house windows, display films for various image display devices (LCDs, organic EL elements, etc.) or mobile terminals (smartphones, tablets, etc.), and films for organic solar cells). Optical films or optical sheets include protective films or protective sheets for imparting a protective function.

[0277] The optical material may be obtained as a molded product obtained 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, when the optical material is an optical lens (e.g., a spectacle lens), the optical lens may be obtained by molding a resin composition into a lens shape.

[0278] The optical material may also be one having a transparent support substrate and a resin layer laminated thereon. In this case, at least one of the support 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 support substrate and a dye-containing layer (so-called resin layer) containing a specific dye laminated thereon, or a protective film or protective sheet having a transparent support substrate and a hard coat layer and an adhesive layer or bonding layer laminated thereon. When the optical material is a protective film or protective sheet, the specific dye may be contained in at least one of the support substrate, the hard coat layer, and the adhesive layer or bonding layer. When the optical material is a protective film or protective sheet, the protective film or protective sheet may be in the form of, for example, an adhesive layer arranged on the support substrate containing the specific dye, and the adhesive layer or bonding layer having both an ultraviolet and blue light blocking function and an adhesive or bonding function.

[0279] The details and preferred embodiments of the dye represented by Formula 1 (i.e., the specific dye), the specific UV agent, and the resin or solvent contained in the optical material, as well as the components other than the specific dye and the resin, are the same as those of the resin composition or liquid composition described above, and therefore will not be described in detail here.

[0280] An embodiment of the optical material will now be described.

[0281] [First Embodiment of Optical Material] The first embodiment is an optical material that is a spectacle lens.

[0282] When the optical material of the present disclosure is applied to eyeglass lenses, it contains a resin. There are no particular restrictions on the resin that can be used for eyeglass lenses, as long as it satisfies the physical properties required for eyeglass lenses, such as transparency, refractive index, processability, and hardness after curing. The resin may be a thermoplastic resin or a thermosetting resin. Examples of thermoplastic resins that can be used for eyeglass lenses include polycarbonate (PC). Examples of thermosetting resins include urethane resins and episulfide resins. Thiourethane resins are preferred as urethane resins. Thiourethane resins are preferred as resins because of their high refractive index, and polycarbonate resins are preferred because of their good transparency. That is, the resin in the eyeglass lenses of the present disclosure is preferably at least one selected from the group consisting of thiourethane resins and polycarbonate resins.

[0283] For details of thiourethane resins and episulfide resins suitable as resins for eyeglass lenses, see JP-A-2009-256692, JP-A-2007-238952, JP-A-2009-74624, JP-A-2015-212395, and JP-A-2016-84381.

[0284] When the optical material of the present disclosure is applied to eyeglass lenses, it may contain only one type of resin, or may contain two or more types. The content of the resin when the optical material of the present disclosure is used as an eyeglass lens is not particularly limited, and is, for example, preferably 30% by mass to 99.99% by mass, more preferably 50% by mass to 99.99% by mass, and even more preferably 60% by mass to 99.99% by mass, relative to the total mass of the eyeglass lens. When the content of the resin in the optical material applied to eyeglass lenses of the present disclosure is within the above range, lightweight and thin lenses can be produced.

[0285] When the optical material of the present disclosure is applied to eyeglass lenses, it may contain other components in addition to the resin, such as ultraviolet absorbers other than the specific UV agent, plasticizers, anti-degradants (e.g., antioxidants, peroxide decomposers, radical inhibitors, metal deactivators, acid scavengers, and amines), dyes other than the specific pigments, internal mold release agents, and deodorizers.

[0286] The method for producing an eyeglass lens is not particularly limited. For example, when the resin contained in the eyeglass lens is a thermoplastic resin, the eyeglass lens of the present disclosure can be produced by kneading a resin composition containing the resin, the compound of the present disclosure described above, and, if necessary, other additives such as an ultraviolet absorber, using a melt extruder, molding the kneaded mixture into pellets, and applying a known molding method such as injection molding to the obtained pellet-shaped resin composition. For example, when the resin contained in the eyeglass lens is a thermosetting resin, the eyeglass lens of the present disclosure can be produced by preparing a resin composition containing a monomer that is a resin precursor, the compound of the present disclosure described above, a polymerization catalyst (e.g., dibutyltin dichloride), and, if necessary, other optional ultraviolet absorbers and other additives, filling the obtained resin composition into a mold (forming die), and curing it by heating.

[0287] [Second embodiment of optical material] A second embodiment of the optical material may be a protective film. Examples of the protective film include an optical material (protective film 1) having a transparent supporting substrate and a resin layer laminated thereto, and an optical material (protective film 2) having a hard coat layer, a transparent supporting substrate, and a pressure-sensitive adhesive layer or bonding layer laminated thereto in this order.

[0288] (Protective Film 1) - Supporting Substrate - The supporting substrate preferably has transparency to the extent that optical performance is not impaired. The supporting substrate being transparent means that it is optically transparent, and specifically means that the supporting substrate has a total light transmittance of 85% or more. The total light transmittance of the supporting substrate is preferably 90% or more, and more preferably 95% or more. The total light transmittance of the supporting substrate is a value determined from the measured value obtained by measuring the spectroscopic spectrum of the supporting substrate using a UV / vis spectrometer (for example, a UV / vis spectrometer UV3400 manufactured by Shimadzu Corporation).

[0289] A suitable example of the support substrate is a resin film. Examples of resins that form the support substrate include ester resins (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), and polycyclohexanedimethylene terephthalate (PCT)), olefin resins (e.g., polypropylene (PP) and polyethylene (PE)), polyvinyl chloride (PVA), and tricellulose acetate (TAC). Among these, PET is preferred as the resin that forms the support substrate in terms of versatility.

[0290] The support substrate can be obtained by molding the above resin into a plate by a standard method. Alternatively, a commercially available resin film or the like may be used as the support substrate.

[0291] The thickness of the supporting substrate can be appropriately selected depending on the application or purpose. In general, the thickness of the supporting substrate is preferably 5 μm to 2500 μm, and more preferably 20 μm to 500 μm.

[0292] Resin Layer The resin layer is a layer formed using the resin composition of the present disclosure described above, or the liquid composition of the present disclosure when it contains a resin. The resin layer may be a resin layer that has been dried and solidified in advance, or may be a cured layer obtained by applying a liquid composition of the liquid composition to a supporting substrate and causing a curing reaction, for example.

[0293] The thickness of the resin layer is not particularly limited and can be arbitrarily selected from the viewpoints of absorbance in the wavelength region of 350 nm to 450 nm (in other words, for example, the content of the specific dye) and the desired visible light transmittance. The thickness of the resin layer can be, for example, 5 μm to 2500 μm. The thickness of the resin layer is preferably 5 μm to 500 μm, more preferably 5 μm to 100 μm, from the viewpoints of being particularly excellent in blocking or suppressing ultraviolet light and blue light, and of easily ensuring visible light transmittance and being easy to handle.

[0294] Formation of Resin Layer A resin layer can be formed by applying (and optionally curing) the resin composition or liquid composition of the present disclosure prepared as a coating liquid to a desired region of a supporting substrate. If the resin composition or liquid composition is curable, energy is applied after application to cause a curing reaction, thereby forming a resin layer that is a cured product of the resin composition or liquid composition.

[0295] When forming the resin layer, the coated film may be dried after application, or when the resin layer is formed by curing, the coated film may be dried after application of the composition but before curing. The coating film can be dried by known methods, such as a method of blowing hot air, a method of passing the coating film through a drying zone controlled to a predetermined temperature, or a method of heating and drying the coating film with a heater provided on a conveying roll.

[0296] The energy can be applied by irradiation with visible light, ultraviolet light (UV), electron beams, or the like, or by heating. Among these, irradiation with visible light or ultraviolet light is preferred as the energy application, and ultraviolet light is more preferred. From the viewpoint of improving curability, it is preferable to dry the coating film in advance to reduce the amount of solvent in the film before curing by applying energy. The drying here can be carried out by the same method as above.

[0297] The application of energy by light irradiation can be carried out using, for example, a light source capable of UV irradiation, such as an ultra-high pressure UV lamp (e.g., an ultra-high pressure mercury lamp) or a UV light emitting diode (UV-LED).

[0298] The irradiation dose is 10 mJ / cm because the curing reaction proceeds well. ２ ~1000mJ / cm ２ The range is preferred.

[0299] When the curing reaction is carried out by irradiation with UV or the like, it is preferable to reduce the oxygen concentration by replacing the atmosphere in the UV irradiation area with an inert gas (e.g., nitrogen gas) from the viewpoint of suppressing curing inhibition by oxygen and further promoting surface curing of the resin layer. The oxygen concentration in the atmosphere in the UV irradiation area is preferably 0.01% to 5%. Furthermore, from the viewpoint of promoting the curing reaction, it is preferable to increase the temperature of the atmosphere in the UV irradiation area. The atmosphere temperature in the UV irradiation area is preferably 25°C to 100°C, more preferably 30°C to 80°C, and even more preferably 40°C to 70°C.

[0300] (Protective Film 2) The protective film 2 is an optical material having a hard coat layer, a transparent supporting substrate, and a pressure-sensitive adhesive layer or adhesive layer laminated in this order, and at least one of the supporting substrate, the hard coat layer, and the pressure-sensitive adhesive layer or adhesive layer contains a specific dye. The specific dye may be contained in any one of the supporting substrate, the hard coat layer, and the pressure-sensitive adhesive layer or adhesive layer, or two or more of the supporting substrate, the hard coat layer, and the pressure-sensitive adhesive layer or adhesive layer may contain the specific dye. That is, in the protective film 2, at least one of the supporting substrate, the hard coat layer, and the pressure-sensitive adhesive layer or adhesive layer is formed using the resin composition or liquid composition of the present disclosure. The protective film 2 is preferably (1) in a form in which at least the hard coat layer is a cured product of the resin composition or liquid composition of the present disclosure, or (2) in a form in which at least the supporting substrate is a cured product of the resin composition or liquid composition of the present disclosure. In the case of (1), the supporting substrate is the same as the protective film 1 except that it may contain a specific dye, and in the case of (2), the supporting substrate is a cured product formed using the resin composition or liquid composition of the present disclosure.

[0301] -Hard Coat Layer- The protective film 2 has a hard coat layer on a supporting substrate. When the optical material has a hard coat layer as the outermost layer, the scratch resistance of the optical material can be improved.

[0302] The hard coat layer may be formed by either a wet coating method or a dry coating method (vacuum film formation). The wet coating method is preferred as a method for forming the hard coat layer from the viewpoint of excellent productivity. When the hard coat layer is formed using the resin composition or liquid composition of the present disclosure, it is formed by the wet coating method.

[0303] When the hard coat layer is not a cured product of the resin composition or liquid composition of the present disclosure, examples of the hard coat layer include those described in JP 2013-45045 A, JP 2013-43352 A, JP 2012-232459 A, JP 2012-128157 A, JP 2011-131409 A, JP 2011-131404 A, JP 2011-126162 A, JP 2011-75705 A, JP 2009-286981 A, JP 2011-126162 A, JP 2011-75705 A, JP 2009-286981 A, JP-A-2009-263567, JP-A-2009-75248, JP-A-2007-164206, JP-A-2006-96811, JP-A-2004-75970, JP-A-2002-156505, JP-A-2001-272503, WO 12 / 018087, WO 12 / 098967, WO 12 / 086659, and the hard coat layer described in WO 11 / 105594 can be applied.

[0304] When the optical material has a hard coat layer, the thickness of the hard coat layer is preferably 5 μm to 100 μm in order to further improve the scratch resistance of the optical material.

[0305] -Adhesive Layer, Bonding Layer- The protective film 2 is an optical material having an adhesive layer or a pressure-sensitive adhesive layer on the side of the supporting substrate opposite to the side having the hard coat layer.

[0306] The type of adhesive or pressure-sensitive adhesive used in the pressure-sensitive adhesive layer or adhesive layer is not particularly limited. Examples of the adhesive include acrylic adhesives, rubber adhesives, and silicone adhesives. The acrylic adhesive refers to an adhesive containing a polymer of a (meth)acrylic monomer (so-called a (meth)acrylic polymer).

[0307] Examples of adhesives include urethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives, and silicone adhesives. Among these, urethane resin adhesives and silicone adhesives are preferred because of their high adhesive strength. Commercially available adhesives may be used, and an example of a commercially available adhesive is a urethane resin adhesive (product name: LIS-073-50U) from Toyo Ink Co., Ltd. The adhesive may also be used in combination with a curing agent (product name: CR-001) from Toyo Ink Co., Ltd.

[0308] When the optical material has a pressure-sensitive adhesive layer or an adhesive layer, the thickness of the pressure-sensitive adhesive layer or adhesive layer is preferably 5 μm to 100 μm in terms of achieving both adhesive strength and ease of handling.

[0309] Hereinafter, 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.

[0310] (Example 1): Synthesis Example (Synthesis of D-33)

[0311]

[0312] According to the above scheme, 3.0 g of 1,2-dibenzylpyrazolidine-3,5-dione, 2.7 g of methyl 2-(3-formylindol-1-yl)propanoate, and 42 ml of methanol were added and heated under reflux for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and the precipitated solid was filtered and washed with methanol to obtain 4.9 g of compound D-33. Yield: 93%.

[0313] The structure of compound D-33 was confirmed by NMR (nuclear magnetic resonance), and the results are shown below. １ H-NMR (CDCl ３ ): δ 9.91 (s, 1H), 8.42 (s, 1H), 7.99 (m, 1H), 7.37 to 7.16 (m, 13H), 5.24 (q, 1H), 4.80 (d, 4H), 3.74 (s, 3H), 1.98 (d, 3H)

[0314] (Example 2): Synthesis Example (Synthesis of D-56)

[0315]

[0316] Compound D-56 was obtained in the same manner as in the synthesis of compound D-33 according to the above scheme, except that methyl 2-(3-formylindol-1-yl)propanoate was changed to methyl 2-(3-formyl-2-methyl-indol-1-yl)propanoate in the synthesis of compound D-33 in Example 1.

[0317] The structure of compound D-56 was confirmed by NMR, and the results are shown below. １ H-NMR (CDCl ３ ): δ 8.32 (s, 1H), 7.76 (d, 1H), 7.37 to 7.16 (m, 13H), 5.24 (q, 1H), 4.81 (m, 4H), 3.72 (s, 3H), 2.58 (s, 3H), 1.82 (d, 3H)

[0318] (Example 3): Synthesis Example (Synthesis of D-35)

[0319]

[0320] Compound D-35 was obtained in the same manner as in the synthesis of compound D-33 in Example 1, except that methyl 2-(3-formylindol-1-yl)propanoate was changed to 1-isopropyl-1H-indole-3-carbaldehyde according to the above scheme.

[0321] The structure of compound D-35 was confirmed by NMR, and the results are shown below. １ H-NMR (CDCl ３ ): δ 9.90 (s, 1H), 8.42 (s, 1H), 7.99 (m, 1H), 7.47 to 7.16 (m, 13H), 4.82 (d, 4H), 4.76 (q, 1H), 1.67 (d, 6H)

[0322] (Example 4): Synthesis Example (Synthesis of D-58)

[0323]

[0324] Compound D-58 was obtained by reacting in the same manner as for D-33 according to the above scheme, except that 1-isopropyl-2-methyl-1H-indole-3-carbaldehyde was used in the synthesis of compound D-33 in Example 1.

[0325] (Example 5): Synthesis Example (Synthesis of D-61)

[0326]

[0327] Compound D-61 was obtained by reacting in the same manner as for D-33 according to the above scheme, except that 1-(2-ethylhexyl)-2-methyl-1H-indole-3-carbaldehyde was used in the synthesis of compound D-33 in Example 1.

[0328] (Evaluation of Compounds) 1. Maximum Absorption Wavelength (λmax) and Molar Absorption Coefficient (ε) Sample solutions were prepared by dissolving 2 mg of each compound listed in Table 1 below in 100 mL of ethyl acetate and then diluting with ethyl acetate so that the solution absorbance was in the range of 0.6 to 1.2. The absorbance and molar absorption coefficient of each sample solution were measured using a spectrophotometer (UV-1800PC, Shimadzu Corporation) in a 1 cm quartz cell. The maximum absorption wavelength (λmax) was measured from the absorption spectrum of each sample solution. The long-wavelength absorption slope was then evaluated according to the following criteria: 2. Long-wavelength Absorption Slope For each sample solution, the absorbance at λmax was divided by the absorbance at a wavelength of λmax + 40 nm to calculate the long-wavelength absorption slope. The larger the long-wavelength absorption slope, the smaller the long-wavelength side absorption and the sharper the absorption. The measurement results are shown in Table 1 below.

[0329]

[0330] From the results in Table 1, it was confirmed that the specific dyes obtained in Examples 1 to 5 have maximum absorption wavelengths in the range of 410 nm to 425 nm, and from the results of the long wavelength absorption slope, the side absorption at long wavelengths is small and the absorption is sharp. Among them, D-35 and D-58, which are included in Formula 4, had sharp absorption.

[0331] 3. Evaluation of specific dyes in resin compositions The specific dyes listed in Table 2 below were weighed out in the amounts shown below and dissolved in 7.6 g of chloroform and 1.1 g of (meth)acrylic resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95,000) to prepare a resin composition. The resulting resin composition was spin-coated onto a glass substrate to form a coating film, and the resulting coating film was dried at 110°C for 2 minutes to produce a resin film.

[0332] The obtained resin film was subjected to a lightfastness test under the following condition 4, and the lightfastness was evaluated by determining the absorbance retention rate at the maximum absorption wavelength (λmax). Specifically, the absorbance of the resin film at λmax was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and then the resin film was subjected to a lightfastness test under condition 4, and the absorbance of the resin film after the lightfastness test at λmax was measured. Next, using the absorbance values ​​at λmax of the resin film before and after the lightfastness test, the absorbance retention rate (%) was calculated according to the following formula, and the lightfastness was evaluated according to the following criteria. A higher absorbance retention rate means better lightfastness. The evaluation results are shown in Table 2 below. The number in parentheses in the lightfastness column is the value of the absorbance retention rate. Absorbance retention rate (%) = (absorbance at λmax of resin film after lightfastness test / absorbance at λmax of resin film before lightfastness test) × 100 (Condition 4) Apparatus: Low-temperature cycle xenon weather meter (XL75, manufactured by Suga Test Instruments Co., Ltd.) Illuminance: 90 klx (40 W / m2) Time: 48 hours Environment: 23°C, relative humidity 50% (lightfastness evaluation)

[0333]

[0334] As shown in Table 2, the specific dyes had good light resistance in the resin composition. In particular, compounds D-33, D-35, D-56, D-58, and D-61, which are specific dyes encompassed by the above formulas 4 and 5, had better light resistance than compound D-25, which is encompassed by formula 1 but not encompassed by formulas 4 and 5.

[0335] (Examples 101 to 132): Resin composition The specific dye and specific UV agent shown in Table 3 below were used in the amounts shown in Table 3, and 7.6 g of chloroform and 1.1 g of commercially available polymethyl methacrylate resin (Dianal BR-80 (PMMA-based polymer containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw: 95,000, acid value: 0 mg KOH / g), manufactured by Mitsubishi Chemical Corporation) were dissolved to prepare a resin solution (i.e., a resin composition). The obtained resin solution was spin-coated onto a glass substrate to form a coating film, and dried at 110 ° C. for 2 minutes to prepare a resin film containing a specific dye or a comparative dye. A resin film with a thickness of 10 μm was formed. In Table 3, "-" indicates that the compound was not included. The specific UV agents used are as follows.

[0336]

[0337]

[0338] (Comparative Examples 101 to 103): Resin Compositions Resin films were formed in the same manner as in Example 101, except that resin compositions containing the specific dyes and not containing the specific UV agents described in Table 3 below were prepared.

[0339] Comparative Examples 104 to 109: Resin Compositions Resin films were formed in the same manner as in Example 101, except that compound D-14 in Example 101 was replaced with the following comparative dye E-1.

[0340]

[0341] (Evaluation of Resin Composition) -1. Heat Resistance- For each of the resin films formed in Examples 101 to 132 and Comparative Examples 101 to 109, a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation) was used to measure absorbance at a wavelength of 600 nm, at which the dye and ultraviolet absorber have no absorption, and the degree of precipitation of the dye and ultraviolet absorber was evaluated. The results are shown in Table 3. A smaller absorbance value indicates a smaller degree of precipitation.

[0342] - Evaluation criteria for precipitation - A: absorbance at 600 nm is less than 0.05 B: absorbance at 600 nm is 0.05 or more and less than 0.10 C: absorbance at 600 nm is 0.10 or more and less than 0.20 D: absorbance at 600 nm is 0.20 or more

[0343]

[0344] The evaluation results in Table 3 above show that the resin compositions of Examples 101 to 132, which contained a specific dye and a specific UV agent, showed almost no precipitation, a level that was practically acceptable. On the other hand, the resin compositions of Comparative Examples 101 to 103, which contained a specific dye but no specific UV agent, showed increased precipitation compared to Examples 127 to 132, which contained the same amount of specific dye. Furthermore, Comparative Examples 104 to 109, which contained a comparative dye, showed precipitation of components, even though they contained a specific UV agent, at a level that was problematic for practical use. That is, as shown in Table 3, even when the content of the specific dye was increased, the use of the specific UV agent in combination suppressed precipitation of components in the resin film formed as a molded product of the resin composition, thereby improving the flexibility of the content of the specific dye in the resin composition.

[0345] (Examples 201 to 216, Comparative Examples 201 to 205): Resin Compositions The specific dyes, comparative dyes, and specific UV agents listed in Table 4 below were weighed out in the amounts listed in Table 4 and dissolved in 7.6 g of chloroform and 1.1 g of (meth)acrylic resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95,000) to prepare a resin composition. The resulting resin composition was spin-coated onto a glass substrate to form a coating film, and the resulting coating film was dried at 110 ° C. for 2 minutes to produce a resin film. In Table 4, "-" indicates that the compound is not included.

[0346] (Evaluation of Resin Composition) - Lightfastness Evaluation 1 - A lightfastness test was performed on each resin film obtained above under the following condition 1, and the lightfastness was evaluated by determining the absorbance retention rate at the maximum absorption wavelength (λmax). Specifically, the absorbance of the resin film at λmax was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and then the resin film was subjected to a lightfastness test under condition 1. The absorbance of the resin film after the lightfastness test at λmax was measured. Next, the absorbance retention rate (%) was calculated using the absorbance values ​​at λmax of the resin film before and after the lightfastness test according to the following formula, and the absorbance retention rate (%) was calculated according to the following formula to evaluate lightfastness. A higher absorbance retention rate means better lightfastness. The evaluation results are shown in Table 4 below. The numerical values ​​in the lightfastness column are the absorbance retention rates of the specific dye, comparative dye, and specific UV agent, respectively. Absorbance retention rate (%) = (absorbance at λmax of resin film after light resistance test / absorbance at λmax of resin film before light resistance test) × 100 (Condition 1) Apparatus: low-temperature cycle xenon weather meter (XL75, manufactured by Suga Test Instruments Co., Ltd.) Illuminance: 90 klx (40 W / m2) Time: 72 hours Environment: 23°C, relative humidity 50%

[0347]

[0348] The evaluation results in Table 4 above show that the resin compositions of Examples 201 to 216 containing a specific dye and a specific UV agent exhibited excellent light resistance, with almost no decrease in the absorbance of the specific dye and specific UV agent contained in the resin composition even after 72 hours of severe exposure. On the other hand, the resin compositions of Comparative Examples 201 to 204, which contained a specific UV agent but used a comparative dye instead of the specific dye, exhibited poor light resistance of the dye, and the light resistance of the specific UV agent was also reduced compared to Examples 201 to 204, which contained the specific dye at the same content. Furthermore, Comparative Example 205, which contained a specific UV agent but did not contain the specific dye, exhibited significantly lower stability of the specific UV agent, indicating that the interaction between the specific dye and the specific UV agent improved the light resistance of the specific UV agent.

[0349] (Examples 301 to 324): Resin composition The specific dyes and specific UV agents shown in Table 5 below were weighed out in the amounts shown in Table 5 and dissolved in 7.6 g of chloroform and 1.1 g of (meth)acrylic resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95,000) to prepare a resin composition. The obtained resin composition was spin-coated onto a glass substrate to form a coating film, and the obtained coating film was dried at 110°C for 2 minutes to produce a resin film.

[0350] (Evaluation of Resin Composition) - Evaluation of Stability of Resin Composition - For each of the obtained resin films, the absorbance at a wavelength of 600 nm, at which the specific dye and specific UV agent do not absorb, was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and the degree of precipitation of the specific dye and specific UV agent was evaluated. The smaller the absorbance value, the smaller the degree of precipitation. The results are shown in Table 5. - Evaluation Criteria for Precipitation - A: Absorbance at 600 nm is less than 0.05 B: Absorbance at 600 nm is 0.05 or more but less than 0.10 C: Absorbance at 600 nm is 0.10 or more but less than 0.20 D: Absorbance at 600 nm is 0.20 or more

[0351]

[0352] From the evaluation results in Table 5 above, it can be seen that the resin compositions of Examples 301 to 324 containing the specific dye and specific UV agent suppress the precipitation of the specific dye and specific UV agent contained in the resin composition, and the stability of the resin composition is excellent over a wide range of content ratios of the specific dye and specific UV agent.

[0353] (Examples 401 to 416, Comparative Examples 401 to 403): Resin Compositions The specific dyes, comparative dyes, specific UV agents, and anti-fading agents listed in Table 6 below were weighed in the amounts listed in Table 6 and dissolved in 7.6 g of chloroform and 1.1 g of (meth)acrylic resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95,000) to prepare a resin composition. The resulting resin composition was spin-coated onto a glass substrate to form a coating film, and the resulting coating film was dried at 110 ° C. for 2 minutes to produce a resin film. In Table 6, "-" indicates that the compound is not included.

[0354] (Evaluation of Resin Composition) - Lightfastness Evaluation 2 - A lightfastness test was performed on each of the obtained resin films under the following condition 2, and the lightfastness was evaluated by determining the absorbance retention rate at the maximum absorption wavelength (λmax). Specifically, the absorbance of the resin film at λmax was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and then the resin film was subjected to a lightfastness test under condition 2. The absorbance of the resin film after the lightfastness test at λmax was measured. Next, the absorbance retention rate (%) was calculated using the absorbance values ​​at λmax of the resin film before and after the lightfastness test according to the following formula, and lightfastness was evaluated according to the following criteria. A higher absorbance retention rate means better lightfastness. The evaluation results are shown in Table 6 below. The number in parentheses in the lightfastness column is the value of the absorbance retention rate. Absorbance retention rate (%) = (absorbance at λmax of resin film after lightfastness test / absorbance at λmax of resin film before lightfastness test) × 100 (Condition 2) Apparatus: Low-temperature cycle xenon weather meter (XL75, manufactured by Suga Test Instruments Co., Ltd.) Illuminance: 90 klx (40 W / m2) Time: 1 week Environment: 23°C, relative humidity 50% (lightfastness evaluation)

[0355] The structure of the anti-fading agent used in the resin composition is shown below.

[0356]

[0357]

[0358] From the evaluation results in Table 6 above, it can be seen that the resin compositions of Examples 401 to 415, which contain a specific dye and a specific UV agent in addition to a discoloration inhibitor, show little decrease in the absorbance of the specific dye and specific UV agent contained in the resin composition, even after a harsh exposure period of one week, demonstrating excellent light resistance. Furthermore, in comparison with Example 416, which does not contain a discoloration inhibitor, and Examples 413 to 415, which contain the same levels of specific dye and specific UV agent and also contain a discoloration inhibitor, improved weather resistance was observed by further incorporating a discoloration inhibitor. On the other hand, it can be seen that the resin compositions of Comparative Examples 401 to 403, which contain a specific UV agent but also use a comparative dye instead of the specific dye, have low light resistance of the dye and low light resistance of the specific UV agent compared to the Examples.

[0359] (Examples 501 to 516, Comparative Examples 501 to 504): Resin Composition The specific dyes, comparative dyes, and specific UV agents listed in Table 7 below were weighed out in the amounts listed in Table 7 and dissolved in 7.6 g of chloroform and 1.1 g of (meth)acrylic resin (Dianal BR-80, manufactured by Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95,000) to prepare a resin composition. The obtained resin composition was spin-coated onto a glass substrate to form a coating film, and the obtained coating film was dried at 110 ° C. for 2 minutes to produce a resin film.

[0360] (Evaluation of Resin Composition) - Evaluation of Moisture and Heat Resistance - The obtained resin film was subjected to a moist heat resistance test under the following condition 3, and the retention rate of absorbance at the maximum absorption wavelength (λmax) was determined to evaluate the moist heat resistance. Specifically, the absorbance of the resin film at λmax was measured using a spectrophotometer (UV-1800PC, manufactured by Shimadzu Corporation), and then the resin film was subjected to a moist heat resistance test under condition 3. The absorbance of the resin film after the moist heat resistance test at λmax was measured. Next, the absorbance retention rate (%) was calculated using the absorbance values ​​at λmax of the resin film before and after the light resistance test according to the following formula, and the moist heat resistance was evaluated according to the following criteria. A higher absorbance retention rate means better moist heat resistance. The evaluation results are shown in Table 7 below. Absorbance retention rate (%)=(absorbance at λmax of resin film after moist heat resistance test / absorbance at λmax of resin film before moist heat resistance test)×100

[0361] Furthermore, the absorbance of the resin film before and after the moist heat resistance test was measured at a wavelength of 600 nm, at which the specific dye, the comparative dye, and the specific UV agent have no absorption, to evaluate the degree of precipitation of the specific dye, the comparative dye, and the specific UV agent. A smaller absorbance value indicates a smaller degree of precipitation.

[0362] (Condition 3) Apparatus: Thermo-humidistat chamber (PR-3KT, manufactured by Espec Corporation) Time: 500 hours Environment: 60°C, relative humidity 90% Evaluation criteria for precipitation A: Absorbance at 600 nm is less than 0.05 B: Absorbance at 600 nm is 0.05 or more and less than 0.10 C: Absorbance at 600 nm is 0.10 or more and less than 0.20 D: Absorbance at 600 nm is 0.20 or more

[0363]

[0364] From the evaluation results in Table 7 above, the resin compositions of Examples 501 to 516 containing a specific dye and a specific UV agent showed almost no decrease in absorbance of the resin composition and no precipitation even after 500 hours in the moist heat resistance test, indicating that the specific dye and specific UV agent contained in the resin composition have excellent moist heat resistance. On the other hand, the resin compositions of Comparative Examples 501 to 504, which contained a specific UV agent but used a comparative dye instead of the specific dye, showed a lower absorbance retention rate of the resin composition compared to the Examples, and showed significant precipitation after the moist heat resistance test.

[0365] The composition, resin composition, and liquid composition of the present disclosure can be applied to optical materials. Optical materials include, for example, optical filters (e.g., optical lenses) and optical films or 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 and contact lenses)); UV-cutting materials that block or suppress ultraviolet (UV) light (e.g., UV-cutting lenses (e.g., eyeglasses and contact lenses), UV-cutting films or UV-cutting sheets (e.g., window films, display films for various image display devices, and display films for mobile devices (smartphones, tablets, etc.)); and UV-cutting glass (e.g., vehicle glass and building glass)). The optical material of the present disclosure is suitable for applications such as improving the durability of LCDs and organic EL devices. In particular, the optical material of the present disclosure is suitable for applications in environments requiring heat resistance and light resistance. Furthermore, the liquid composition and the dye compound of the present disclosure are suitable for use in environments where heat resistance and light resistance are required, and can be suitably used in applications such as inks, paints, etc. Furthermore, the dye compound of the present disclosure can also be added to a pressure-sensitive adhesive for use.

[0366] Examples of image display devices include devices such as liquid crystal displays (LCDs), plasma display panels, electroluminescence (EL) displays, and cathode ray tube displays. Furthermore, image display devices include not only large-area image display devices but also portable terminals such as smartphones and tablet terminals equipped with touch panels. The touch panel is not particularly limited and 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. Incidentally, touch panels include so-called touch sensors and touch pads.

[0367] The disclosure of Japanese Patent Application No. 2023-123593, filed on July 28, 2023, is incorporated herein by reference. All documents, patent applications, and technical standards mentioned in this disclosure 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 composition comprising a dye represented by the following formula 1 and at least one ultraviolet absorber selected from the following compound group I: In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent; R ５ and R ６ may be bonded to each other to form a 6-membered ring. Compound Group I: Benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, acrylate compounds, benzoxazinone compounds, benzoxazole compounds, and benzodithiol compounds.

2. The composition according to claim 1, wherein the ultraviolet absorber comprises at least one compound selected from the group consisting of compounds represented by the following formula (2-1), (2-2), (2-3) and (2-4): In formula (2-1), R １１ and R １２ each independently represents a hydrogen atom or a substituent, and n11 and n12 each independently represent an integer of 1 to 3. ２１ and R ２２ Each of n21 and n22 independently represents an integer of 1 to 3. ３１ , R ３２ and R ３３ Each of n31, n32, and n33 independently represents an integer of 1 to 3. ４１ , R ４２ , R ４３ , R ４４ , R ４５ , R ４６ and R ４７ each independently represents a hydrogen atom or a substituent.

3. The composition according to claim 1 or 2, wherein the content ratio of the dye to the ultraviolet absorber is in the range of 1:20 to 20:1 on a mass basis.

4. A resin composition comprising a dye represented by the following formula 1, at least one ultraviolet absorber selected from the following compound group I, and a resin. In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent; R ５ and R ６ may be bonded to each other to form a 6-membered ring. Compound Group I: Benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, acrylate compounds, benzoxazinone compounds, benzoxazole compounds, and benzodithiol compounds.

5. A liquid composition comprising a dye represented by the following formula 1, at least one ultraviolet absorber selected from the following compound group I, and a solvent. In formula 1, R １ and R ２ each independently represents an alkyl group or an aryl group; R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a substituent; R ５ and R ６ may be bonded to each other to form a 6-membered ring. Compound Group I: Benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, acrylate compounds, benzoxazinone compounds, benzoxazole compounds, and benzodithiol compounds.

6. The composition according to claim 1 or 2, further comprising at least one anti-fading agent selected from the group consisting of amine compounds, phenol compounds, hydroquinone compounds, catechol compounds, ascorbic acid compounds, carotenoid compounds, metal complex compounds and benzolactone compounds.

7. The composition according to claim 6, wherein the content ratio of said dye to said anti-fading agent is in the range of 1:20 to 20:1 by mass.

8. The composition according to claim 6, wherein the anti-fading agent comprises at least one compound selected from the group consisting of compounds represented by the following formula (3-1) and formula (3-2): In formula (3-1), R ａ１ , R ａ２ , R ａ３ and R ａ４ each independently represents a hydrogen atom, an alkyl group or an alkenyl group; ａ１ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, an alkoxycarbonyloxy group, an alkenyloxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a carbamoyl group, a hydroxy group, or an oxy radical group; X ａ２ represents an atomic group necessary to form a 5- to 7-membered ring. ｐ１ represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, or -Si(R ｐ１０１ ) (Rp １０２ ) (Rp １０３ ), R ｐ１０１ , Rp １０２ and Rp １０３ each independently represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkenyloxy group, or an aryloxy group; R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ each independently represents a hydrogen atom or a substituent; R ｐ１ , R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ Any two adjacent groups among R may be bonded to each other to form a ring; ｐ１ , R ｐ２ , R ｐ３ , R ｐ４ , R ｐ５ and R ｐ６ Not all of the atoms are hydrogen atoms.

9. An optical material which is a cured product of the composition according to claim 1, the resin composition according to claim 4, or the liquid composition according to claim 5.

10. A dye compound represented by the following formula 4: In formula 4, R ４１ represents a hydrogen atom, an alkyl group, or an aryl group. ４１ When represents a hydrogen atom, R ４２ represents a secondary alkyl group having a branched structure at a carbon atom directly bonded to a nitrogen atom, a tertiary alkyl group having a branched structure at a carbon atom directly bonded to a nitrogen atom, or an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms; R ４１ When represents an alkyl group or an aryl group, R ４２ represents a hydrogen atom or a substituent. ４３ , R ４４ , R ４５ and R ４６ each independently represents a hydrogen atom or a substituent.

11. A dye compound represented by the following formula 5: In formula 5, R ５１ represents a hydrogen atom, a methyl group, or a phenyl group. ５１ When represents a hydrogen atom, R ５２ represents a secondary alkyl group having a branched structure at a carbon atom directly bonded to a nitrogen atom, a tertiary alkyl group having a branched structure at a carbon atom directly bonded to a nitrogen atom, or an unsubstituted linear primary alkyl group having 1 to 6 carbon atoms; R ５１ When represents an alkyl group or an aryl group, R ５２ represents a hydrogen atom or a substituent. ５３ , R ５４ , R ５５ and R ５６ each independently represents a hydrogen atom or a substituent 12. An optical material comprising the dye compound according to claim 10 or 11.

13. The optical material according to claim 12, which is a spectacle lens.

14. The optical material according to claim 12, which is a protective sheet.

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