Resin composition, liquid composition, pigment compound and optical material

Abstract

A resin composition and a liquid composition, a pigment compound and an optical material comprising a pigment and a resin represented by Formula 1. 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 With R 6 They can bond to each other to form a 6-membered ring. #imgabs0#

Description

Technical Field

[0001] The invention relates to a resin composition, a liquid composition, a pigment compound and an optical material. Background Art

[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 and the like may affect the human body (particularly the eyes), and therefore are a concern.

[0003] Regarding ultraviolet rays (UV), we provide UV-cutting materials such as glass, films, and eyeglass lenses that use components that absorb UV rays, as well as daily necessities such as UV care cosmetics and sunscreens.

[0004] In recent years, the effect of blue light contained in the light emitted from the display of an image display device such as a liquid crystal display device or the display of a mobile device such as a smartphone on the eyes has attracted attention, and eye fatigue caused by blue light has become a problem. Therefore, eyeglass lenses or protective films that use components that absorb blue light have been proposed, not only for ultraviolet rays but also for blue light with a wavelength of 380nm to 500nm.

[0005] On the one hand, as an example of a dye used to dye a layer of a silver halide photographic light-sensitive material, a compound having a pyrazolone ring and an indole ring in the molecular structure is disclosed (for example, refer to Japanese Patent No. 2707371). In addition, as a dye used for the same purpose, there is an invention related to a compound having a pyrazolidinedione skeleton (for example, refer to Japanese Patent No. 2681525 and Japanese Patent Laid-Open No. 11-193353). In Japanese Patent Laid-Open No. 11-193353, since the oil-soluble dye has a portion where the hydrogen atom on the nitrogen atom is dissociated, the hydrophilicity of the entire molecule becomes high in the alkali color development treatment, showing excellent decolorization.

[0006] On the other hand, materials that use components that absorb ultraviolet and blue light are often used in environments that are continuously exposed to sunlight or high-temperature environments, such as eyeglass lenses and vehicle windows. Therefore, it is desirable that the components that absorb ultraviolet and blue light have a certain degree of resistance to light and heat. Summary of the invention

[0007] Technical issues to be solved by the invention

[0008] Research has been conducted on technologies for shielding ultraviolet light and blue light. However, it is not yet possible to provide a pigment that can obtain high absorbance in the wavelength region of 280nm to 500nm and can stably maintain high absorbance even in an exposed environment or a high-temperature environment. For pigments that can withstand use in an environment where they may be continuously exposed to light and heat (for example, an outdoor environment), it is expected that their use in components used or installed outdoors will be expanded.

[0009] The pigments disclosed in the Japanese Patent No. 2707371, Japanese Patent No. 2681525 and Japanese Patent Application Laid-Open No. 11-193353 are effective for dyeing the layer of silver halide photosensitive materials and are excellent in decolorization after dyeing due to their structure. However, it is estimated that there is still room for improvement in terms of shielding ability against ultraviolet rays and blue light having absorption wavelengths on the shorter wavelength side than the visible region.

[0010] The present invention has been accomplished in view of the above circumstances.

[0011] An object of the embodiments of the present invention is to provide a resin composition and a liquid composition having high absorbance at least in the wavelength region of 350 nm to 450 nm and excellent light resistance and heat resistance.

[0012] Another embodiment of the present invention aims to provide a novel dye compound having high absorbance at least in the wavelength region of 350 nm to 450 nm and excellent light resistance and heat resistance.

[0013] Another embodiment of the present invention aims to provide an optical material having high absorbance in at least a wavelength range of 350 nm to 450 nm and suitable for use in an exposure environment and a high-temperature environment.

[0014] Means for solving technical problems

[0015] Specific solutions to the problem include the following.

[0016] <1> A resin composition comprises a pigment represented by the following formula 1 and a resin.

[0017] [Chemical formula 1]

[0018]

[0019] 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 6Each independently represents a hydrogen atom or a substituent, R 5 With R 6 They may be bonded to each other to form a 6-membered ring.

[0020] <2> according to <1> The resin composition, wherein R 1 represents an alkyl group, R 2 represents an alkyl group or an aryl group.

[0021] <3> according to <1> or <2> The resin composition, wherein R 1 and R 2 Each independently represents an alkyl group.

[0022] <4> according to <1> The resin composition, wherein R 1 and R 2 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 At least one of represents a hydrogen atom.

[0023] <5> A liquid composition comprising a pigment represented by the following formula 1 and a solvent.

[0024] [Chemical formula 2]

[0025]

[0026] 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 With R 6 They may be bonded to each other to form a 6-membered ring.

[0027] <6> according to <5> The liquid composition, wherein R 1 represents an alkyl group, R 2 represents an alkyl group or an aryl group.

[0028] <7> according to <5> or <6> The liquid composition, wherein R 1 and R 2 Each independently represents an alkyl group.

[0029] <8> according to <5> The liquid composition, wherein R 1 and R 2 Each independently represents an aryl group, R3 , R 5 and R 6 Each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 3 and R 6 At least one of represents a hydrogen atom.

[0030] <9> according to <5> to <8> The liquid composition as described above is used for ink or coating.

[0031] <10> A pigment compound represented by the following formula 2.

[0032] [Chemical formula 3]

[0033]

[0034] In formula 2, R 1 represents an alkyl group or an aryl group.

[0035] When R 1 When it represents an alkyl group, R 12 represents an alkyl or aryl group, R 3 , R 5 and R 6 Each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 4 represents a hydrogen atom, an alkyl group, an aryl group or an amino group, R 5 With R 6 They may be bonded to each other to form a 6-membered ring.

[0036] When R 1 When it represents an aryl group, R 12 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 At least one of them represents a hydrogen atom, R 4 represents a hydrogen atom, an alkyl group, an aryl group or an amino group, R 5 With R 6 can bond to each other to form a 6-membered ring. 1 and R 12 The exception is the case where the aryl group in the formula (I) is substituted by a group having a sulfonamide structure.

[0037] <11> according to <10> The pigment compound, wherein R 1 and R 12 Each independently represents an alkyl group.

[0038] <12> An optical material, which is <1> to <4> The resin composition described in any one of the above <5> to <8> A solidified product of any one of the liquid compositions.

[0039] <13> An optical material includes a pigment represented by the following formula 1.

[0040] [Chemical formula 4]

[0041]

[0042] 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 With R 6 They may be bonded to each other to form a 6-membered ring.

[0043] <14> according to <12> or <13> The optical material is a spectacle lens.

[0044] <15> according to <12> or <13> The optical material is a protective sheet.

[0045] Effects of the Invention

[0046] According to an embodiment of the present invention, there are provided a resin composition and a liquid composition having high absorbance in at least a wavelength region of 350 nm to 450 nm and excellent light resistance and heat resistance.

[0047] According to another embodiment of the present invention, there is provided a novel dye compound having high absorbance in at least a wavelength region of 350 nm to 450 nm and excellent light resistance and heat resistance.

[0048] According to another embodiment of the present invention, there is provided an optical material having high absorbance in at least a wavelength region of 350 nm to 450 nm and suitable for use in an exposure environment and a high-temperature environment. DETAILED DESCRIPTION

[0049] Hereinafter, the contents of the present invention will be described in detail.

[0050] Although the description of the constituent elements described below may be based on representative embodiments of the present invention, the present invention is not limited to such embodiments.

[0051] In addition, in the present invention, "to" indicating a numerical range is used to mean that the numerical values ​​described before and after it are included as the lower limit and the upper limit.

[0052] In the numerical ranges recorded in stages in this specification, the upper limit or lower limit recorded in one numerical range can be replaced by the upper limit or lower limit of other numerical ranges recorded in stages. Moreover, in the numerical ranges recorded in the present invention, the upper limit or lower limit of the numerical range can also be replaced by the value shown in the embodiment.

[0053] In the present invention, compounds not explicitly described as substituted or unsubstituted may have any substituent within a range not impairing the effects of the present invention.

[0054] In the present invention, when a plurality of substances corresponding to each component are present in a layer, the amount of each component in the composition refers to the total amount of the plurality of substances present in the composition unless otherwise specified.

[0055] In addition, in the present invention, a combination of preferred embodiments is a more preferred embodiment.

[0056] <Resin composition>

[0057] The resin composition of the present invention contains a pigment (hereinafter also referred to as a specific pigment) and a resin represented by the following formula 1. The resin composition of the present invention may further contain other pigments other than the specific pigment, an ultraviolet absorber, and other components as necessary.

[0058] The present inventors have found that a dye having a structure in which a pyrazolidinedione skeleton and a pyrrole skeleton are linked via a methine group as shown in Formula 1 has high absorption particularly in the wavelength region of 350 nm to 450 nm and is strong against heat and light.

[0059] The resin composition of the present invention includes a specific pigment having a structure in which a pyrazolidinedione skeleton and a pyrrole skeleton are connected by a methine as in Formula 1, so at least the absorbance of the wavelength light of 350nm to 450nm is high, and the light resistance and heat resistance are excellent. Therefore, if the resin composition of the present invention is used, it is possible to obtain a resin body having a high absorbance of at least 350nm to 450nm wavelength light by a known molding method, and having excellent light resistance and heat resistance. Specifically, for example, a material (e.g., a molded article such as glass, a film, a thin sheet, a lens, etc.) that blocks or suppresses ultraviolet (UV) and blue light can be provided.

[0060] (pigment)

[0061] The resin composition of the present invention contains the pigment represented by Formula 1 (ie, specific pigment).

[0062] The pigment represented by Formula 1 (ie, specific pigment) is a yellow pigment having high absorbance in the wavelength range of 280 nm to 500 nm, at least in the wavelength range of 350 nm to 450 nm, and preferably in the wavelength range of 380 nm to 450 nm.

[0063] The specific coloring matter in the present invention includes dyes and pigments.

[0064] [Chemical formula 5]

[0065]

[0066] 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 With R 6 They may be bonded to each other to form a 6-membered ring.

[0067] R 1 and R 2 The alkyl group in may be an unsubstituted alkyl group or a substituted alkyl group substituted with a substituent.

[0068] 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, an n-propyl group, an isopropyl group, and a cyclohexyl group.

[0069] As the substituent of the substituted alkyl group, there can be mentioned substituents included in the following substituent group A.

[0070] (Substituent Group A)

[0071] a halogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, a carboxyl group (which may be in the form of a salt), an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic group, an acyloxy group, a carbamoyloxy group, a sulfonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an anilino group, an alkylamino group, an acylamino group, an aminocarbonylamino group, an alkylcarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a sulfonamido group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclicthio group, a sulfamoyl group, a sulfo group (which may be in the form of a salt), 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 imido group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a silyl group, and the like

[0072] 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 hydroxyl group.

[0073] As the substituted alkyl group substituted with a substituent, a substituted alkyl group having 1 to 12 carbon atoms in total is preferred, and examples thereof include a benzyl group, a hydroxybenzyl group, and a methoxyethyl group.

[0074] In addition, when R 1 and R 2 When both represent an alkyl group, the alkyl groups may be the same or different.

[0075] R 1 and R 2 The aryl group in may be an unsubstituted aryl group or a substituted aryl group substituted with a substituent.

[0076] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, and an example thereof is a phenyl group.

[0077] As the substituent of the substituted aryl group, the substituents included in the above-mentioned substituent group A can be mentioned.

[0078] Preferred examples of the substituent for the substituted aryl group include a halogen atom (for example, a chlorine atom, a bromine atom and an iodine atom), a hydroxyl group, a carboxyl group, a sulfonamide group, an amino group, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; for example, a methyl group, an ethyl group, a n-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 n-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 n-propoxycarbonyl group and an isopropoxycarbonyl group), a sulfonyloxy group and a monovalent group formed by linking at least two of them.

[0079] As the substituted aryl group substituted with a substituent, an aryl group having a total carbon number of 6 to 18 is preferred, and examples thereof include 4-chlorophenyl, 2,5-dichlorophenyl, hydroxyphenyl, 4-carboxyphenyl, 3,5-dicarboxyphenyl, 4-methanesulfonylaminophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-(2-hydroxyethoxy)phenyl, N,N-dimethylaminophenyl, 4-(N-carboxymethyl-N-ethylamino)phenyl, 4-ethoxycarbonylphenyl and 4-methanesulfonyloxyphenyl.

[0080] In addition, when R 1 and R 2 When they all represent aryl groups, the aryl groups may be the same or different.

[0081] As R 3 , R 4 , R 5 and R 6The substituent in can include the substituents included in the above-mentioned substituent group A.

[0082] In the substituent group A, R 3 , R 5 and R 6 An alkyl group or an aryl group is preferred.

[0083] As R 3 , R 5 and R 6 , preferably each independently represents a hydrogen atom, an alkyl group or an aryl group.

[0084] In the substituent group A, R 4 An alkyl group, an aryl group or an amino group is preferred.

[0085] As R 4 , preferably represents a hydrogen atom, an alkyl group, an aryl group or an amino group.

[0086] R 3 , R 5 and R 6 The alkyl group in may be an unsubstituted alkyl group or a substituted alkyl group substituted with a substituent.

[0087] 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, an n-propyl group, and an isopropyl group.

[0088] As R 3 , R 5 and R 6 The substituents of the substituted alkyl group in the above-mentioned substituent group A can be mentioned.

[0089] Preferred examples of the substituent of the substituted alkyl group include a phenyl group, a carboxyl group, and a hydroxyl group.

[0090] As the substituted alkyl group substituted with a substituent, an alkyl group having 1 to 8 carbon atoms in total is preferred, and examples thereof include a benzyl group, a carboxymethyl group, and a hydroxymethyl group.

[0091] In addition, when R 3 , R 5 and R 6 When both represent an alkyl group, the alkyl groups may be the same or different.

[0092] R 3 , R 5 and R 6 The aryl group in may be an unsubstituted aryl group or a substituted aryl group substituted with a substituent.

[0093] The unsubstituted aryl group is preferably an aryl group having 6 to 10 carbon atoms, and an example thereof is a phenyl group.

[0094] As R 3 , R 5 and R 6 The substituents of the substituted aryl group in include the substituents included in the above-mentioned substituent group A.

[0095] 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 hydroxyl group, a carboxyl group, and an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; for example, a methyl group, an ethyl group, a n-propyl group, and an isopropyl group).

[0096] The substituted aryl group substituted with a substituent is preferably an aryl group having 6 to 10 carbon atoms in total, and examples thereof include 4-chlorophenyl, 2,5-dichlorophenyl, hydroxyphenyl, carboxyphenyl, 3,5-dicarboxyphenyl and 4-methylphenyl.

[0097] When R 5 and R 6 When R is a substituent, from the viewpoint of light resistance and heat resistance, 3 Preferred is a hydrogen atom.

[0098] In addition, when R 3 , R 5 and R 6 When they all represent aryl groups, the aryl groups may be the same or different.

[0099] R 4 The alkyl group in may be an unsubstituted alkyl group or a substituted alkyl group substituted with a substituent.

[0100] 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, an n-propyl group, an isopropyl group, and a cyclohexyl group.

[0101] As R 4 The substituents of the substituted alkyl group in the above-mentioned substituent group A can be mentioned.

[0102] Preferred examples of the substituent of the substituted alkyl group include phenyl, carboxyl, hydroxyl, alkyl (preferably an alkyl group having 1 to 4 carbon atoms; for example, methyl, ethyl, n-propyl and isopropyl), alkoxy (preferably an alkoxy group having 1 to 4 carbon atoms; for example, methoxy, ethoxy, n-propoxy and isopropoxy), alkoxycarbonyl (preferably an alkoxycarbonyl group having 2 to 5 carbon atoms; for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl and isopropoxycarbonyl), alkylamino (preferably an alkylamino group having 1 to 4 carbon atoms; for example, dimethylamino), alkylcarbonylamino (preferably an alkylcarbonylamino group having 1 to 4 carbon atoms; for example, methylcarbonylamino), cyano and a monovalent group formed by linking at least two of them.

[0103] As the substituted alkyl group substituted with a substituent, an alkyl group having a total carbon number of 1 to 18 is preferred, and examples thereof include benzyl, carboxybenzyl, hydroxybenzyl, methoxycarbonylethyl, ethoxycarbonylmethyl, 2-cyanoethyl, 2-propionylaminoethyl, dimethylaminomethyl, methylcarbonylaminopropyl, di(methoxycarbonylmethyl)aminopropyl and phenacylmethyl.

[0104] R 4 The aryl group in may be an unsubstituted aryl group or a substituted aryl group substituted with a substituent.

[0105] The unsubstituted aryl group is preferably an aryl group having 6 to 12 carbon atoms, and an example thereof is a phenyl group.

[0106] As R 4 The substituents of the substituted aryl group in include the substituents included in the above-mentioned substituent group A.

[0107] Preferred examples of the substituent for the substituted aryl group include a halogen atom (for example, a chlorine atom, a bromine atom and an iodine atom), a hydroxyl group, a carboxyl group, a sulfonamide group, an amino group, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms; for example, a methyl group, an ethyl group, a n-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 n-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 n-propoxycarbonyl group and an isopropoxycarbonyl group), a sulfonyloxy group and a monovalent group formed by linking at least two of them.

[0108] As the substituted aryl group substituted with a substituent, an aryl group having a total carbon number of 6 to 22 is preferred, and examples thereof include 4-chlorophenyl, 2,5-dichlorophenyl, hydroxyphenyl, 2,5-methoxyphenyl, 2-methoxy-5-ethoxycarbonylphenyl, 4-methoxycarbonylphenyl, 4-ethoxycarbonylphenyl, 4-butoxycarbonylphenyl, 4-octyloxycarbonylphenyl, 4-carboxyphenyl, 3,5-dicarboxyphenyl, 4-methanesulfonylaminophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-(2-hydroxyethoxy)phenyl, N,N-dimethylaminophenyl, N,N-diethylaminophenyl, 4-(N-carboxymethyl-N-ethylamino)phenyl, 4-{N,N-bis(ethoxycarbonylmethyl)amino}phenyl, 4-{bis(ethoxycarbonylmethyl)amino}carbonylphenyl, 4-ethoxycarbonylphenyl, 4-methanesulfonyloxyphenyl, 4-acetylsulfamoylphenyl, 4-propionylsulfamoylphenyl and 4-methanesulfonamidophenyl.

[0109] R 4 The amino group in may be an unsubstituted amino group or a substituted amino group substituted with a substituent.

[0110] Examples of the substituent of the substituted amino group include the same substituents as those of the substituted alkyl group.

[0111] 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.

[0112] 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 methylamino, dimethylamino, diethylamino, and pyrrolidinyl groups.

[0113] R 5 With R 6 They may be bonded to each other to form a 6-membered ring.

[0114] R 5 With R 6 The 6-membered ring formed by bonding to each other is preferably a benzene ring.

[0115] R in Formula 1 1 and R 2 Among them, R 1 More preferably, R 1 represents an alkyl group and R 2 For the same reason, R is further preferably 1 and R 2 When each independently represents an alkyl group, it is particularly preferred that they represent an alkyl group having 1 to 8 carbon atoms.

[0116] And, in Formula 1, R 1 and R 2 Among them, R 1 and R 2 All of them represent the case of aryl group.

[0117] When R 1 and R 2 When each independently represents an aryl group, preferably 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 In the case where at least one of represents a hydrogen atom. Among them, from the viewpoint of heat resistance and light resistance, R 3 represents a hydrogen atom, R 5 and R 6 When each independently represents an alkyl group or an aryl group, it is more preferred that R 3 represents a hydrogen atom, R 5 and R 6When each independently represents an alkyl group, R 3 represents a hydrogen atom, R 5 and R 6 Each independently represents an alkyl group, and R 5 and R 6 The specific dye is preferably a case where the specific dye has a structure represented by the following formula 1-1.

[0118] [Chemical formula 6]

[0119]

[0120] R in Formula 1-1 1 ~R 4 Respectively with R in Formula 1 1 ~R 4 The meanings are the same and the preferred aspects are also the same.

[0121] R 15 represents a substituent. 15 The substituent represented by can be exemplified by the substituents included in the above-mentioned substituent group A. 15 , preferably an alkyl group, an aryl group, a halogen atom, an acyl group or an alkoxycarbonyl group.

[0122] R 15 The alkyl and aryl groups in R 3 , R 5 and R 6 The alkyl group and the aryl group in are synonymous, and the preferred embodiments are also the same.

[0123] As R 15 Examples of the halogen atom include a chlorine atom, a bromine atom and an iodine atom.

[0124] As R 15 Examples of the acyl group include acetyl, propionyl and butyryl.

[0125] As R 15 The alkoxycarbonyl group in the above-mentioned group is preferably an alkoxycarbonyl group having 2 to 5 carbon atoms, and examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl and isopropoxycarbonyl.

[0126] Specific examples of the dye (ie, specific dye) represented by the above formula 1 are shown below.

[0127] However, the present invention is not limited to these specific examples. In addition, "Me" in the specific examples represents a "methyl group".

[0128] [Chemical formula 7]

[0129]

[0130] [Chemical formula 8]

[0131]

[0132] [Chemical formula 9]

[0133]

[0134] ~Synthesis~

[0135] As shown below, the dye (specific dye) represented by Formula 1 can be synthesized by mixing the pyrazolidinedione represented by Formula 3 and the aldehyde represented by Formula 4 in an organic solvent at room temperature (25° C.) or under reflux.

[0136] [Chemical formula 10]

[0137]

[0138] As the organic solvent, for example, alcohol (eg, methanol and ethanol), acetonitrile, N,N-dimethylformamide (DMF), pyridine, acetic acid, and acetic anhydride can be used.

[0139] During the synthesis, a catalyst may be added.

[0140] As the catalyst, for example, piperidine, glycine, β-alanine, p-toluenesulfonic acid, and ammonium acetate can be used.

[0141] After refluxing, the reaction mixture may be cooled to room temperature (ie, 25° C.) to allow precipitation.

[0142] Furthermore, after the precipitated solid is collected by filtration, it may be washed with an organic solvent. For washing, the same organic solvent as that used in the synthesis may be used.

[0143] The resin composition of the present invention may contain one kind of the dye represented by Formula 1 (ie, specific dye) alone, or may contain two or more kinds.

[0144] The content of the pigment (ie, specific pigment) represented by Formula 1 in the resin composition of the present invention is preferably 0.01% by mass to 5% by mass, and more preferably 0.1% by mass to 2% by mass, based on the total solid content of the resin composition.

[0145] The pigment represented by Formula 1 (i.e., specific pigment) has a high absorbance in the wavelength region of 350nm to 450nm, so if the content of the specific pigment in the resin composition of the present invention is within the above range, the resin composition of the present invention becomes a resin composition having excellent blocking function or inhibition function of wavelength light of 350nm to 450nm. Specific pigments, for example, can well block or inhibit ultraviolet light and blue light.

[0146] (resin)

[0147] The resin composition of the present invention contains at least one resin.

[0148] The resin can be appropriately selected from resins that satisfy various physical properties such as transparency, refractive index, and processability required according to the application or purpose.

[0149] The resin may be a thermoplastic resin or a thermosetting resin.

[0150] Examples of the resin include (meth)acrylic resins, epoxy resins, ene-thiol resins, carbonate resins, ether resins, allyl ester resins, sulfone resins, ethersulfone resins, phenylene resins, arylene ether phosphine oxide resins, imide resins, amide imide resins, olefin resins, cyclic olefin resins, ester resins, styrene resins, polyurethane resins, cellulose acylate resins, and episulfide resins.

[0151] Examples of the (meth)acrylic resin include polymers containing structural units derived from (meth)acrylic acid and / or its esters. Specifically, examples include polymers obtained by polymerizing at least one compound selected from the group consisting of (meth)acrylic acid, (meth)acrylic esters, (meth)acrylamide, and (meth)acrylonitrile.

[0152] Examples of the ester resin include polymers obtained by the reaction of a polyol (e.g., ethylene glycol, propylene glycol, glycerin, and trimethylolpropane) with a polyacid (e.g., an aromatic dicarboxylic acid (e.g., terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, and dicarboxylic acids in which hydrogen atoms of the aromatic rings are substituted with methyl, ethyl, or phenyl groups), an aliphatic dicarboxylic acid having 2 to 20 carbon atoms (e.g., adipic acid, sebacic acid, and dodecanedicarboxylic acid), or an alicyclic dicarboxylic acid (e.g., cyclohexane dicarboxylic acid)), and polymers obtained by ring-opening polymerization of a cyclic ester compound such as a caprolactone monomer (e.g., polycaprolactone).

[0153] Examples of the epoxy resin include bisphenol A epoxy resin, bisphenol F epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, aliphatic epoxy resin, etc. Commercially available epoxy resins may be used, and examples of commercially available epoxy resins include the following.

[0154] 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).

[0155] Examples of commercially available bisphenol F-type epoxy resins include jER806, jER807, jER4004, jER4005, jER4007 and jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON830 and EPICLON835 (all manufactured by DIC Corporation), and LCF-21 and RE-602S (all manufactured by Nippon Kayaku Co., Ltd.).

[0156] Examples of commercially available products of the phenol novolac epoxy resin 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).

[0157] Examples of commercially available products 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.).

[0158] Examples of commercially available aliphatic epoxy resins include ADEKA RESIN EP series (e.g., EP-4080S, EP-4085S, and EP-4088S; manufactured by ADEKA CORPORATION), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CFLOXIDE 2085, EHPE3150, EPOLEAD PB 3600, and EPOLEAD PB 4700 (all manufactured by Daicel Corporation), Denacol EX-212L, EX-214L, EX-216L, EX-321L, and EX-850L (all manufactured by Nagase Chemtex Corporation), ADEKA RESIN 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).

[0159] In addition, examples of commercially available 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 NOFCORPORATION, and are epoxy group-containing polymers).

[0160] The resin may have acid groups.

[0161] Examples of the acid group include a carboxyl group, a phosphoric acid group, a sulfonic acid group, and a phenolic hydroxyl group. The acid group may be present in one type or in two or more types.

[0162] A resin having an acid group can be used as the alkali-soluble resin, and can also be used as a dispersant.

[0163] As the resin having an acid group, a polymer having a carboxyl group in a side chain is preferred.

[0164] Examples of resins having an acid group include methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, partially esterified maleic acid copolymers, alkali-soluble phenol resins such as novolac resins, acidic cellulose derivatives having a carboxyl group on the side chain, and resins obtained by adding anhydride to a polymer having a hydroxyl group.

[0165] Among the resins having an acid group, copolymers of (meth)acrylic acid and other monomers copolymerizable with (meth)acrylic acid are particularly suitable as the alkali-soluble resin.

[0166] Examples of other monomers copolymerizable with (meth)acrylic acid include alkyl (meth)acrylates, aryl (meth)acrylates, and vinyl compounds.

[0167] Examples of the alkyl (meth)acrylate and the aryl (meth)acrylate 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, toluyl (meth)acrylate, naphthyl (meth)acrylate, and cyclohexyl (meth)acrylate.

[0168] As other monomers copolymerizable with (meth)acrylic acid, N-substituted maleimide monomers described in JP-A-10-300922 (for example, N-phenylmaleimide and N-cyclohexylmaleimide) and the like can be used.

[0169] Examples of the vinyl compound include styrene, α-methylstyrene, vinyltoluene, glycidyl methacrylate, acrylonitrile, vinyl acetate, N-vinylpyrrolidone, tetrahydrofurfuryl methacrylate, polystyrene macromonomers, and polymethyl methacrylate macromonomers.

[0170] In addition, the other monomer copolymerizable with (meth)acrylic acid may be one kind or two or more kinds.

[0171] Examples of the resin having an acid group include benzyl (meth)acrylate / (meth)acrylic acid copolymers, benzyl (meth)acrylate / (meth)acrylic acid / 2-hydroxyethyl (meth)acrylate copolymers, benzyl (meth)acrylate / (meth)acrylic acid / other monomer copolymers, 2-hydroxyethyl (meth)acrylate polymers, 2-hydroxypropyl (meth)acrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymers described in JP-A-7-140654, 2-hydroxy-3-phenoxypropyl acrylate / polymethyl methacrylate macromonomer / benzyl methacrylate / methacrylic acid copolymers, 2-hydroxyethyl methacrylate / polystyrene macromonomer / methyl methacrylate / methacrylic acid copolymers, and 2-hydroxyethyl methacrylate / polystyrene macromonomer / benzyl methacrylate / methacrylic acid copolymers.

[0172] As the resin having an acid group, reference can be made to paragraphs 0558 to 0571 of Japanese Patent Application Publication No. 2012-208494 (paragraphs 0685 to 0700 of the corresponding U.S. Patent Application Publication No. 2012 / 0235099) and paragraphs 0076 to 0099 of Japanese Patent Application Publication No. 2012-198408, which are incorporated herein. In addition, as the resin having an acid group, ACRYBASE FF-426 (manufactured by NIPPON SHOKUBAI CO., LTD.) can also be used.

[0173] The acid value of the resin having an acid group is preferably 30 mgKOH / g to 200 mgKOH / g. As the lower limit of the acid value, it is more preferably 50 mgKOH / g or more, and further preferably 70 mgKOH / g or more. And, as the upper limit of the acid value, it is more preferably 150 mgKOH / g or less, and further preferably 120 mgKOH / g or less.

[0174] The acid value of the resin is a value measured in accordance with JIS K0070 (1992) and calculated by converting 1 mmol / g=56.1 mgKOH / g.

[0175] The resin may have a curable group.

[0176] The resin is preferably a copolymer containing a structural unit having a curable group.

[0177] As a curable group, a group which has an ethylenically unsaturated bond, an epoxy group, a methylol group, and an alkoxysilyl group are mentioned, for example.

[0178] As a group which has an ethylenically unsaturated bond, a vinyl group, a (meth)allyl group, and a (meth)acryloyl group are mentioned, for example.

[0179] Examples of the alkoxysilyl group include a monoalkoxysilyl group, a dialkoxysilyl group, and a trialkoxysilyl group.

[0180] As a structural unit which has a curable group, the structural unit represented by following formula (A2-1) - (A2-4) is mentioned, for example.

[0181] [Chemical formula 11]

[0182]

[0183] X 1 represents a hydrogen atom or an alkyl group.

[0184] X 1 The number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.

[0185] X 1 A hydrogen atom or a methyl group is preferred.

[0186] L 51 It represents a single bond or a divalent linking group.

[0187] As L 51 The divalent connecting group in can be exemplified by an alkylene group, an arylene group, -O-, -S-, -CO-, -COO-, -OCO-, -SO2-, -NR- (R represents a hydrogen atom or an alkyl group, preferably a hydrogen atom), or a group formed by combining two or more of them.

[0188] As L 51 The divalent linking group in is preferably a group formed by combining at least one selected from an alkyl group and an arylene group with -O-.

[0189] L 51 The number of carbon atoms of the alkylene group in is preferably 1 to 30, more preferably 1 to 15, and further 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.

[0190] L 51 The arylene group in preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and further preferably 6 to 10 carbon atoms.

[0191] Y 1 represents a curable group.

[0192] Examples of the curable group include a group having an ethylenically unsaturated bond, an epoxy group, a methylol group, an alkoxysilyl group, etc. The details of the group having an ethylenically unsaturated bond, an epoxy group, a methylol group, and an alkoxysilyl group are as described above.

[0193] As the resin containing the assimilative group, a commercially available product that has been put on the market can also be used. Examples of commercially available products of the resin containing the 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 (COOH-containing polyurethane acrylic oligomer; Diamond Shamrock Co. Ltd.), Viscoat R-264 and KS Resist 106 (both manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.), CYCLOMER P series (for example, ACA230AA), PLACCEL CF200 series (both manufactured by Daicel Corporation), Ebecryl 3800 (manufactured by Daicel-Allnex Ltd.), and Acrycure-RD-F8 (manufactured by NIPPON SHOKUBAI CO., LTD.). Furthermore, for example, commercially available products of the above-mentioned epoxy resins can also be mentioned.

[0194] For example, when the resin composition of the present invention is used for lenses (eg, eyeglass lenses), the resin is preferably a thermoplastic resin such as a carbonate resin, a (meth)acrylic resin (eg, polymethyl methacrylate (PMMA)) or a thermosetting resin such as a polyurethane resin.

[0195] Examples of commercially available carbonate resins that have been marketed include a polycarbonate resin composition (trade name: CALIBRE 200-13, manufactured by Sumitomo Dow Limited) and a diethylene glycol bisallyl carbonate resin (trade name: CR-39, manufactured by PPG Industries, Inc.).

[0196] As the polyurethane resin, a thiourethane resin is preferred. Examples of commercially available products of raw materials of thiourethane resins that have been marketed include thiourethane resin monomers (trade names: MR-7, MR-8, MR-10, and MR-174; manufactured by Mitsui Chemicals, Inc.).

[0197] The weight average molecular weight (Mw) of the resin is preferably 2,000 to 2,000,000.

[0198] The lower limit of the Mw of the resin is more preferably 5,000 or more, further 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, further preferably 500,000 or less, and particularly preferably 200,000 or less.

[0199] When 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, particularly preferably 500,000 or less. The lower limit of the Mw of the epoxy resin is more preferably 2,000 or more.

[0200] The weight average molecular weight (Mw) is a value measured by gel permeation chromatography (GPC).

[0201] In the measurement based on GPC, HLC (registered trademark)-8020GPC (manufactured by Tosoh Corporation) was used as a measuring device, 3 TSKgel (registered trademark) Super Multipore HZ-H (4.6 mmID×15 cm, manufactured by Tosoh Corporation) were used as columns, and THF (tetrahydrofuran) was used as an eluent. In addition, as measurement conditions, the sample concentration was set to 0.45% by mass, the flow rate was set to 0.35 ml / min, the sample injection amount was set to 10 μl, and the measurement temperature was set to 40° C., and an RI detector was used for the measurement.

[0202] The calibration curve was prepared using eight samples of "TSK standard, polystyrene" manufactured by Tosoh Corporation: "F-40", "F-20", "F-4", "F-1", "A-5000", "A-2500", "A-1000" and "n-propylbenzene".

[0203] The resin composition of the present invention may contain one type of resin alone, or may contain two or more types of resin.

[0204] The content of the resin in the resin composition of the present invention is preferably 70% by mass to 99.9% by mass, and more preferably 80% by mass to 99.9% by mass, based on the total solid content of the resin composition.

[0205] When the content of the resin in the resin composition of the present invention is within the above range, moldability during molding becomes good.

[0206] (Colorants other than specified colorants)

[0207] The resin composition of the present invention may contain a coloring matter (for example, a dye and a pigment) other than the above-mentioned specific coloring matter as necessary depending on the application or purpose.

[0208] Examples of dyes other than specific pigments include phthalocyanine dyes, xanthene dyes, triarylmethane dyes, methine dyes, azo dyes, and anthraquinone dyes described as phthalocyanine compounds in U.S. Patent No. 2008 / 0076044A1, and dipyrromethene dyes described in Japanese Patent Application Laid-Open No. 2008-292970.

[0209] Dyes other than the specific pigment may or may not have a maximum absorption wavelength in the wavelength range of 450 nm to 500 nm.

[0210] As dyes other than the specific pigment, from the viewpoint of better expressing the blocking function and suppressing function of ultraviolet light and blue light, phthalocyanine dyes, xanthene dyes, triarylmethane dyes, methine dyes, azo dyes, anthraquinone dyes, dipyrromethene dyes, etc. are preferred.

[0211] Examples of pigments other than the specific coloring matter include perylene, perinone, quinacridone, quinacridonequinone, anthraquinone, anthraquinone, benzimidazolone, disazo condensation, disazo, azo, indanthrene, phthalocyanine, triarylcarbonium, dioxazine, aminoanthraquinone, diketopyrrolopyrrole, indigo, thioindigo, isoindoline, isoindolinone, pyranthrone, and isoanthrone violet.

[0212] When the resin composition of the present invention contains a pigment other than the specific coloring matter, the average primary particle size 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, from the viewpoint of visibility when used as an optical material.

[0213] When the resin composition of the present invention contains a pigment, it is preferably contained in the resin composition by mixing the pigment with a dispersant, an organic solvent, etc. in advance to prepare a pigment dispersion in which the pigment is dispersed, and then mixing the pigment with other components.

[0214] (Ultraviolet light absorber)

[0215] The resin composition of the present invention may contain an ultraviolet absorber as necessary.

[0216] When a UV absorber is used, the effect of blocking or suppressing UV rays of the resin composition of the present invention can be further enhanced.

[0217] Examples of the ultraviolet absorber include ultraviolet absorbing compounds selected from the group consisting of benzotriazole compounds, triazine compounds, benzophenone compounds, merocyanine compounds, cyanine compounds, dibenzoylmethane compounds, cinnamic acid compounds, acrylate compounds, benzoate compounds, oxalic acid diamide compounds, formamidine compounds, benzoxazinone compounds, benzoxazole compounds and benzodithiol compounds. The ultraviolet absorber that can be used in the resin composition of the present invention is described, for example, in "Fine Chemical" (May 2004 issue) pages 28 to 38, "New Developments in Functional Additives for Polymers" (Toray Research Center, 1999) published by the Research and Development Department of Toray Research Center, Inc., pages 96 to 140, "Development and Environmental Measures for Polymer Additives" (CMC Publishing, 2003) supervised by Masaichi Ohkatsu, pages 54 to 64, and "Degradation and Discoloration Mechanism of Polymers and Its Stabilization Technology - Technical Knowledge Collection -" (TECHNICAL INFORMATION INSTITUTE CO., LTD., 2006) published by TECHNICAL INFORMATION INSTITUTE CO., LTD., and can also be appropriately selected from the compounds described in these documents according to the purpose.

[0218] Examples of the ultraviolet absorber include the following compounds.

[0219] Examples of the benzoxazole compound include compounds represented by the general formula (II) described as fluorescent whitening agents in Japanese Patent No. 4311869.

[0220] Examples of the benzoxazinone compounds include compounds described in Japanese Patent Nos. 5591453 and 5250289.

[0221] Examples of the merocyanine compounds include compounds described in JP-A No. 2011-184414.

[0222] Examples of the benzodithiol-based compound include compounds described in Japanese Patent Nos. 5450994 and 5364311.

[0223] Specific examples of the benzoxazinone-based compound include UV-1, UV-2, and UV-3 having the following structures.

[0224] [Chemical formula 12]

[0225]

[0226] Specific examples of the merocyanine compounds include UV-4 and UV-5 having the following structures.

[0227] [Chemical formula 13]

[0228]

[0229] Specific examples of the benzoxazole-based compound include UV-6 and UV-7 having the following structures.

[0230] [Chemical formula 14]

[0231]

[0232] Specific examples of the benzodithiol-based compound include UV-8 and UV-9 having the following structures.

[0233] [Chemical formula 15]

[0234]

[0235] When the resin composition of the present invention contains an ultraviolet absorber, the ultraviolet absorber may be contained alone or in combination of two or more.

[0236] When the resin composition of the present invention contains a UV absorber, the content of the UV absorber in the resin composition may be appropriately selected depending on the type of the UV absorber, and can generally be 0.01% by mass to 20% by mass relative to the total mass of the resin composition.

[0237] (Other ingredients)

[0238] The resin composition of the present invention may contain components other than the above components (so-called other components).

[0239] Examples of other components include fillers, surfactants, polymerizable compounds, polymerization initiators, adhesion promoters, antioxidants, ultraviolet absorbers, and deflocculants.

[0240] As for the polymerizable compound and the polymerization initiator, the compounds that can be used in the liquid composition described later can be used in the same manner, and therefore, description thereof is omitted here.

[0241] The resin composition of the present invention can be prepared by mixing the pigment represented by Formula 1 (ie, specific pigment) and a resin, and optionally, mixing an ultraviolet absorber and other components.

[0242] <Liquid Composition>

[0243] The liquid composition of the present invention comprises a pigment represented by Formula 1 (ie, a specific pigment) and a solvent.

[0244] Since the liquid composition of the present invention contains a specific dye, it is excellent in shielding properties at least in the wavelength region of 350 nm to 450 nm, and is excellent in light resistance and heat resistance.

[0245] Liquid composition of the present invention can also comprise other pigments, ultraviolet light absorber and other compositions beyond the specific pigment as required.In addition, the details about other pigments, ultraviolet light absorber and other compositions beyond the specific pigment are identical with the situation in the resin combination of the present invention of having been narrated, therefore omit explanation at this.

[0246] (pigment)

[0247] The colorant represented by Formula 1 (ie, specific colorant) contained in the liquid composition of the present invention has the same meaning as the specific colorant in the resin composition of the present invention described above, and preferred aspects are also the same.

[0248] As R in Formula 1 1 and R 2 In particular, from the viewpoint of light resistance, R 1 is an alkyl group, more preferably R 1 represents an alkyl group, and R 2 For the same reason, R is further preferably 1 and R 2 Each of them independently represents an alkyl group.

[0249] And, in Formula 1, R 1 and R 2 Among them, R 1 and R 2 All of them represent aromatic groups. 1 and R 2 When each independently represents an aryl group, preferably 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 At least one of them represents the case of a hydrogen atom.

[0250] The liquid composition of the present invention may contain one kind of the dye (specific dye) represented by Formula 1 alone, or may contain two or more kinds.

[0251] The content of the pigment (specific pigment) represented by Formula 1 in the liquid composition of the present invention is preferably 0.01% by mass to 20% by mass, more preferably 0.1% by mass to 5% by mass, based on the total solid content of the liquid composition.

[0252] The pigment (specific pigment) represented by Formula 1 has a high absorbance particularly in the wavelength region of 350 nm to 450 nm. Therefore, if the content of the specific pigment in the liquid composition of the present invention is within the above range, the liquid composition of the present invention becomes a liquid composition having an excellent function of blocking or suppressing light of a wavelength of 350 nm to 450 nm.

[0253] (Solvent)

[0254] The liquid composition of the present invention contains at least one solvent.

[0255] Examples of the solvent include water, organic solvents, and mixed solvents of water and organic solvents.

[0256] As water, distilled water, ion-exchanged water, or the like can be used.

[0257] The organic solvent can be appropriately selected according to the use and purpose of the liquid composition, etc. Examples of the organic solvent include esters, ethers, ketones, and aromatic hydrocarbons.

[0258] Examples of the ester include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl 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, etc. (specifically, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc.)), alkyl 2-oxypropionate solvents. Agents (for example, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc. (specifically, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, etc.)), 2-oxy-2-methylpropionic acid alkyl ester solvents (methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate (specifically, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.)), methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutyrate, ethyl 2-oxobutyrate, cyclohexyl acetate and 1-methyl-2-methoxyethyl propionate.

[0259] Examples of the ether 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.

[0260] Examples of the ketone include methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone.

[0261] Preferred examples of the aromatic hydrocarbon include toluene and xylene.

[0262] The liquid composition of the present invention may contain one kind of organic solvent alone, or may contain two or more kinds of organic solvents from the viewpoint of application, improvement of the solubility of each component, or coating surface state.

[0263] When the liquid composition of the present invention contains two or more organic solvents, it preferably contains 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.

[0264] The content of the solvent in the liquid composition of the present invention 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.

[0265] The liquid composition of the present invention can be used as a composition having curability (so-called curable composition).

[0266] The curable composition is a composition that can be cured by imparting energy. The curable composition is preferably a composition that exhibits curability by imparting energy such as visible light, ultraviolet light (UV), electron beam, etc., irradiation or heating. Among them, as a curable composition, from the viewpoint of having versatility and good curing sensitivity, a composition that exhibits curability by irradiation with ultraviolet light is more preferred.

[0267] (Polymerizable compound)

[0268] The liquid composition of the present invention can be prepared as a curable composition containing a polymerizable compound in addition to the above-mentioned components. As the polymerizable compound, any compound that can be polymerized and cured when energy is applied can be used without limitation.

[0269] Examples of the polymerizable compound include addition polymerizable compounds having at least one ethylenically unsaturated double bond.

[0270] The addition polymerizable compound can be selected from compounds having at least one ethylenically unsaturated bond at the terminal, and preferably compounds having two or more ethylenically unsaturated bonds at the terminal.

[0271] The polymerizable compound may be, for example, any of a monomer, a prepolymer (ie, a dimer, a trimer or an oligomer), a mixture thereof, and a polymer of a compound selected from the group consisting of a monomer and a prepolymer.

[0272] Examples of polymerizable compounds 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 them, preferred polymerizable compounds are esters of unsaturated carboxylic acids and aliphatic polyols, amides of unsaturated carboxylic acids and aliphatic polyamines, and homopolymers or copolymers thereof.

[0273] In addition, examples of polymerizable compounds include addition reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having nucleophilic substituents (e.g., hydroxyl, amino, and mercapto) with monofunctional or polyfunctional isocyanate compounds or epoxy compounds; dehydration condensation reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having nucleophilic substituents with monofunctional or polyfunctional carboxylic acids; addition reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having electrophilic substituents (e.g., isocyanate and epoxy) with monofunctional or polyfunctional alcohols, amines, or thiols; substitution reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having leaving substituents (e.g., halide and p-toluenesulfonyloxy) with monofunctional or polyfunctional alcohols, amines, or thiols, etc. Furthermore, examples of polymerizable compounds include compounds obtained by substituting the above-mentioned unsaturated carboxylic acids with unsaturated phosphonic acids, styrenes, or vinyl ethers.

[0274] When the liquid composition of the present invention contains a polymerizable compound, details such as the structure of the polymerizable compound, selection of use alone or in combination of two or more, and content may be arbitrarily set according to the use or purpose of the liquid composition.

[0275] For example, from the viewpoint of the curing sensitivity of the liquid composition, as the polymerizable compound, a compound having a large content of groups having ethylenically unsaturated double bonds (also referred to as unsaturated groups) per molecule is preferred, and a difunctional or higher compound having an unsaturated group number of 2 or more is more preferred. Also, for example, from the viewpoint of improving the strength of the resin layer formed by applying the liquid composition, etc., as the polymerizable compound, a trifunctional or higher compound having an unsaturated group number of 3 or more (e.g., a hexafunctional acrylate compound) is preferred.

[0276] Furthermore, the liquid composition of the present invention may use a plurality of compounds having different functional groups or a plurality of compounds having different types of polymerizable groups (e.g., acrylate, methacrylate, styrene-based compounds, and vinyl ether-based compounds) as polymerizable compounds. By using a plurality of polymerizable compounds, both sensitivity and strength can be adjusted.

[0277] As the polymerizable compound, commercially available products that have been put on the market can also be used. Examples of commercially available products of the polymerizable compound include KYARAD (registered trademark) PET-30 and KYARAD (registered trademark) TPA-330 from Nippon Kayaku Co., Ltd., POLYVEST (registered trademark) 110M from EVONIK, and multifunctional acrylate A-9300 (trade name) from Shin-Nakamura Chemical Co., Ltd.

[0278] When the liquid composition of the present invention contains a polymerizable compound, the polymerizable compound may be contained alone or in combination of two or more.

[0279] The content of the polymerizable compound in the liquid composition of the present invention is not particularly limited.

[0280] When the liquid composition of the present invention contains a polymerizable compound, the content of the polymerizable compound in the liquid composition is preferably 30% to 99.5% by mass, more preferably 50% to 99% by mass, and further preferably 60% to 98% by mass, relative to the total solid content of the liquid composition.

[0281] A high molecular weight compound can also be used as the polymerizable compound in the liquid composition of the present invention.

[0282] Examples of the high molecular weight polymerizable compound include (meth)acrylic resins, ester resins, polyurethane resins, and fluorine-based resins.

[0283] Commercially available products of the polymerizable polymer compound may also be used. Examples of commercially available products of the polymerizable polymer compound include Dianal BR series (polymethyl methacrylate (PMMA), such as Dianal BR-80, BR-83 and BR-87; manufactured by Mitsubishi Chemical Corporation), Photomer 6173 (COOH-containing polyurethane acrylic oligomer, Diamond Shamrock Co. Ltd.), Viscoat R-264 and KS Resist 106 (manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.), CYCLOMER P series (such as ACA230AA) and PLACCEL CF200 series (manufactured by Daicel Corporation), Ebecryl 3800 (manufactured by Daicel-Allnex Ltd.), and Acrycure-RD-F8 (manufactured by NIPPON SHOKUBAI CO., LTD.).

[0284] When the liquid composition of the present invention contains a high molecular weight polymerizable compound, the high molecular weight polymerizable compound may be contained alone or in combination of two or more. However, from the viewpoint of film uniformity, it is preferably contained alone.

[0285] From the viewpoint of improving the strength after curing, the polymerizable compound of the macromolecular weight is preferably a compound capable of forming a crosslinked structure. The method for forming the crosslinked structure is not particularly limited, and examples thereof include: a method of using a polymerizable compound of the macromolecular weight and a multifunctional (meth)acrylate monomer having an unsaturated group that can be addition polymerized with the unsaturated group possessed by the polymerizable compound of the macromolecular weight; or a method of using a polymerizable compound of the macromolecular weight (e.g., a (meth)acrylic resin) having a reactive group (e.g., a hydroxyl group) introduced therein and a crosslinking agent having a crosslinking group that can react with the reactive group.

[0286] Examples of the reactive group include groups containing active hydrogen, and specific examples thereof include groups selected from the group consisting of a hydroxyl group, a primary amino group, and a secondary amino group.

[0287] As the polymerizable compound having a high molecular weight into which a reactive group is introduced, for example, a (meth)acrylic resin having a structural unit derived from a (meth)acrylic acid ester monomer and having two or more active hydrogen-containing groups is preferred.

[0288] As the crosslinking agent, polyisocyanates having two or more isocyanate groups as crosslinking groups can be cited. Commercially available products that have been put on the market can also be used as the crosslinking agent. Examples of commercially available products of the crosslinking agent include AD-TMP and A-9550 (both trade names) of Shin-Nakamura Chemical Co., Ltd., etc.

[0289] Among them, as a method for forming a crosslinked structure, a method of using a (meth) acrylic resin having two or more (preferably three or more) groups containing active hydrogen and 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 combination is preferred. In this method, a crosslinked structure can be formed by reacting the groups containing active hydrogen with the isocyanate groups.

[0290] The above method is preferred from the viewpoint that the crosslinking density in the formed resin body (for example, resin layer) is further increased and the strength of the resin body is further increased.

[0291] When the liquid composition of the present invention contains a polymerizable compound, the content of the polymerizable compound in the liquid composition is preferably 30% to 99.5% by mass, more preferably 50% to 99% by mass, and further preferably 60% to 98% by mass, relative to the total solid content of the liquid composition.

[0292] When a polymerizable polymer compound having a reactive group introduced therein and a crosslinking agent are used in combination, the content of the crosslinking agent in the liquid composition is preferably 5 to 80 parts by mass, more preferably 10 to 50 parts by mass, based on 100 parts by mass of the polymerizable polymer compound.

[0293] (Polymerization initiator)

[0294] The liquid composition of the present invention may further comprise a polymerization initiator in addition to the components described above. If the liquid composition of the present invention further comprises a polymerization initiator, the polymerization reaction of the polymerizable compound can be initiated well. As the polymerization initiator, a compound that can generate the initiating species required for the polymerization reaction by imparting energy can be used.

[0295] The polymerization initiator can be appropriately selected from, for example, photopolymerization initiators and thermal polymerization initiators. As the polymerization initiator, a photopolymerization initiator is preferred.

[0296] The photopolymerization initiator is preferably a compound that absorbs light in the ultraviolet region to the visible region (eg, 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.

[0297] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives such as a photopolymerization initiator having a triazine skeleton and a photopolymerization initiator 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; ketone oxime ethers; aminoacetophenone compounds; hydroxyacetophenone, and the like.

[0298] Examples of the aminoacetophenone-based initiator include initiators having an absorption wavelength at 365 nm or 405 nm described in JP-A-2009-191179 and initiators described in JP-A-10-291969.

[0299] Furthermore, examples of the aminoacetophenone-based initiator include acylphosphine oxide-based initiators described in Japanese Patent No. 4225898.

[0300] As the photopolymerization initiator, a synthetic product may be used, or a commercially available product may be used.

[0301] Examples of commercially available photopolymerization initiators include hydroxyacetophenone-based 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); aminoacetophenone-based initiators such as IRGACURE (registered trademark) 907, IRGACURE (registered trademark) 369, and IRGACURE (registered trademark) 379 (trade names: all manufactured by BASF); and acylphosphine-based initiators such as IRGACURE (registered trademark) 819 and DAROCUR (registered trademark) TPO (trade names: all manufactured by BASF).

[0302] As the photopolymerization initiator, an oxime compound is preferred.

[0303] Specific examples of oxime compounds include compounds described in Japanese Patent Application Publication No. 2001-233842, compounds described in Japanese Patent Application Publication No. 2000-80068, compounds described in Japanese Patent Application Publication No. 2006-342166, and compounds described in paragraphs 0073 to 0075 of Japanese Patent Application Publication No. 2016-6475. In addition, as for the photopolymerization initiator, among the oxime compounds, oxime ester compounds are preferred, and examples of commercial products that have been put on the market include IRGACURE-OXE01 and IRGACURE-OXE02 (both manufactured by BASF).

[0304] Examples of the cationic polymerization initiator include initiators for initiating photocationic polymerization, photodecolorizers of pigment compounds, photochromic agents, known acid generators used in microresists, and mixtures thereof. Specifically, examples of the cationic polymerization initiator include onium compounds, organic halogen compounds, and disulfone compounds.

[0305] Examples of the onium compound include diazonium salts, ammonium salts, iminium salts, phosphonium salts, iodonium salts, sulfonium salts, arsonium salts, and selenium salts. Examples of the onium compound include compounds described in paragraphs 0058 to 0059 of Japanese Patent Application Laid-Open No. 2002-29162.

[0306] When the liquid composition of the present invention contains a polymerization initiator, the polymerization initiator may be contained alone or in combination of two or more.

[0307] When the liquid composition of the present invention contains a polymerization initiator, the content of the polymerization initiator in the liquid composition is preferably 0.1% to 20% by mass, more preferably 0.3% to 15% by mass, and further preferably 0.4% to 10% by mass, relative to the total solid content of the liquid composition.

[0308] The liquid composition of the present invention can be prepared by mixing the pigment represented by Formula 1 (ie, specific pigment) and a solvent, and optionally, a polymerizable compound, a polymerization initiator, an ultraviolet absorber, and other components.

[0309] <Pigment compound>

[0310] The pigment compound of the present invention is a pigment compound represented by Formula 2 below.

[0311] The dye compound represented by Formula 2 represents a part of the dye represented by Formula 1, and the compound within the range represented by Formula 2 is a novel dye compound.

[0312] [Chemical formula 16]

[0313]

[0314] In formula 2, R 1 represents an alkyl group or an aryl group.

[0315] R in Formula 2 1 The alkyl or aryl group in formula 1 and R 1 The alkyl group or aryl group in is synonymous with each other, and the preferred aspects are also the same.

[0316] When R 1 When it represents an alkyl group, R 12 represents an alkyl or aryl group, R3 , R 5 and R 6 Each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 4 represents a hydrogen atom, an alkyl group, an aryl group or an amino group, R 5 With R 6 They may be bonded to each other to form a 6-membered ring.

[0317] On the other hand, when R 1 When it represents an aryl group, R 12 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 At least one of them represents a hydrogen atom, R 4 represents a hydrogen atom, an alkyl group, an aryl group or an amino group, R 5 With R 6 can bond to each other to form a 6-membered ring, but R 1 and R 12 The exception is the case where the aryl group in the formula (A) is substituted by a group having a sulfonamide structure (-SO2NH-).

[0318] The group having a sulfonamide structure means a sulfonamide group or a substituted form thereof.

[0319] When R 1 and R 12 When it represents an aryl group, R is more preferably 1 and R 12 The aryl group in does not include an aryl group substituted by a dissociative group.

[0320] The dissociative group refers to a group that can be ionized by the separation of a hydrogen atom, and includes a group having a sulfonamide structure, a sulfone group, a phosphonic acid group, a carboxyl group, a hydroxyl group, and the like.

[0321] In formula 2, R 1 and R 12 Among them, R 1 For the same reason, R is more preferably 1 and R 12 When each independently represents an alkyl group, it is more preferable to represent an alkyl group having 1 to 8 carbon atoms.

[0322] R in Formula 2 12 The alkyl and aryl groups in formula 1 are respectively 2 The alkyl group and the aryl group in are synonymous, and the preferred embodiments are also the same.

[0323] R in Formula 2 3 , R 5 and R6 The alkyl and aryl groups in formula 1 are respectively 3 , R 5 and R 6 The alkyl group and the aryl group in are synonymous, and the preferred embodiments are also the same.

[0324] R in Formula 2 4 The alkyl, aryl and amino groups in formula 1 are respectively 4 The alkyl group, aryl group and amino group in are synonymous, and the preferred embodiments are also the same.

[0325] And, R in Formula 2 5 With R 6 The 6-membered ring formed by bonding with each other and R 5 With R 6 The 6-membered ring formed by bonding to each other has the same meaning and the preferred embodiment is also the same.

[0326] As specific examples of the dye compound represented by the above formula 2, compounds included in the range represented by formula 2 among the above compounds cited as specific examples of the dye represented by formula 1 can be cited.

[0327] However, in the present invention, the pigment compound represented by Formula 2 is not limited to the compounds shown in the specific examples.

[0328] As shown in the scheme described in the resin composition section, the pigment compound represented by Formula 2 can be synthesized by mixing the pyrazolidinedione represented by Formula 3 and the aldehyde represented by Formula 4 in an organic solvent at room temperature (ie, 25° C.) or under reflux.

[0329] The temperature and time during reflux, the organic solvent, the catalyst, and the details of cooling and washing after reflux are the same as those for the dye represented by Formula 1, and thus the description thereof is omitted here.

[0330] <Optical Materials>

[0331] The optical material of the present invention is a cured product of the resin composition or liquid composition of the present invention described above.

[0332] Therefore, the optical material of the present invention contains at least the pigment (ie, specific pigment) represented by the above-mentioned formula 1. Therefore, the optical material of the present invention has excellent shielding properties in the wavelength region of 350 nm to 450 nm, and is excellent in light resistance and heat resistance.

[0333] The “cured product” in the present invention includes a dried product obtained by drying a resin composition or a liquid composition and a cured product obtained by causing a resin composition or a liquid composition to undergo a curing reaction when the resin composition or the liquid composition undergoes a curing reaction.

[0334] Examples of optical materials include optical filters (e.g., optical lenses) and optical films or optical sheets (e.g., films for windows of vehicles or houses, films for displays of various image display devices (LCDs, organic EL elements, etc.) or portable terminals (smartphones, tablet computers, etc.), and films for organic solar cells). The optical film or optical sheet includes a protective film or protective sheet for imparting a protective function.

[0335] Optical material can be obtained as a molded product formed by molding a resin composition into a desired shape. That is, the optical material can be a molded product molded by 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 can be obtained by molding the resin composition into a lens shape.

[0336] Furthermore, the optical material may have a transparent supporting substrate and a resin layer laminated thereon. In this case, at least one of the supporting substrate and the resin layer is formed of a resin composition or a liquid composition.

[0337] The optical material may be, for example, an optical film or optical sheet having a transparent supporting substrate and a pigment layer (so-called resin layer) containing a specific pigment in a stacked manner, or a protective film or protective sheet having a transparent supporting substrate and a hard coating layer and a close layer or adhesive layer in a stacked manner. When the optical material is a protective film or protective sheet, the specific pigment may be included in at least one of the supporting substrate, the hard coating layer and the close layer or adhesive layer. When the optical material is a protective film or protective sheet, the protective film or protective sheet may be, for example, a bonding layer disposed on the supporting substrate including a specific pigment, and the close layer or adhesive layer has both ultraviolet and blue light blocking functions and close functions or adhesive functions.

[0338] The details and preferred embodiments of the dye (ie, specific dye) and resin represented by Formula 1 and components other than the specific dye and resin contained in the optical material are the same as those of the resin composition described above, and thus the details are omitted here.

[0339] Embodiments of the optical material will be described.

[0340] [First embodiment of optical material]

[0341] The first embodiment is an optical material including a transparent supporting substrate and a resin layer laminated thereon.

[0342] Examples of the optical material of the first embodiment include an optical film or an optical sheet, or a protective film or a protective sheet.

[0343] -Supporting substrate-

[0344] The supporting substrate preferably has transparency within a range not impairing optical performance.

[0345] The support substrate being transparent means being optically transparent, and specifically means that the total light transmittance of the support substrate is 85% or more.

[0346] The total light transmittance of the supporting substrate is preferably 90% or more, more preferably 95% or more.

[0347] The total light transmittance of the supporting substrate is a value obtained from a measured value obtained by measuring the spectral spectrum of the supporting substrate using a UV / vis spectrometer (for example, UV / vis spectrometer UV3400 manufactured by SHIMADZU CORPORATION).

[0348] As the supporting substrate, a resin film can be mentioned as a preferred example.

[0349] Examples of the resin for forming the supporting substrate include ester resins (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), and polycyclohexane dimethyl terephthalate (PCT)), olefin resins (e.g., polypropylene (PP) and polyethylene (PE)), polyvinyl chloride (PVA), and cellulose triacetate (TAC).

[0350] Among them, as the resin forming the supporting substrate, PET is preferred from the viewpoint of versatility.

[0351] The supporting substrate is obtained by molding the above-mentioned resin into a plate shape by a conventional method. Alternatively, a commercially available resin film or the like may be used as the supporting substrate.

[0352] The thickness of the support substrate can be appropriately selected according to the application or purpose. Usually, the thickness of the support substrate is preferably 5 μm to 2500 μm, more preferably 20 μm to 500 μm.

[0353] -Resin layer-

[0354] The resin layer is a layer formed using the resin composition of the present invention described above or the liquid composition of the present invention when containing a resin.

[0355] The resin layer may be a layer that is dried and cured, or may be a cured layer obtained by a curing reaction.

[0356] 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 pigment) and desired visible light transmittance.

[0357] The thickness of the resin layer can be, for example, 5 μm to 2500 μm.

[0358] In particular, from the viewpoint of more excellent function of blocking or suppressing ultraviolet rays and blue light and from the viewpoint of easy securing of visible light transmittance and easy handling, the thickness of the resin layer is preferably 5 μm to 500 μm, more preferably 5 μm to 100 μm.

[0359] - Formation of resin layer -

[0360] The resin layer can be formed by applying (and curing, if necessary) the resin composition or liquid composition of the present invention prepared as a coating liquid to a desired region of a supporting substrate.

[0361] When the resin composition or liquid composition has curability, a resin layer which is a cured product of the resin composition or liquid composition can be formed by applying energy to cause a curing reaction to proceed.

[0362] After coating (or before curing when curing is performed), the coating film formed by coating may be dried.

[0363] The coating film can be dried by a known method such as a method of blowing warm air, a method of passing through a drying zone controlled in advance to a predetermined temperature, a method of drying by heating with a heater provided on a transport roller, or the like.

[0364] The energy can be provided by irradiation with visible light, ultraviolet light (UV), electron beam, or the like, or by heating. Among these, the energy provided is preferably provided by irradiation with visible light or ultraviolet light, and more preferably by irradiation with ultraviolet light.

[0365] From the viewpoint of improving curability, it is preferred to dry the coating film in advance to reduce the amount of solvent in the film before curing by applying energy. Here, drying can be performed by the same method as described above.

[0366] The energy imparted by irradiation with light can be performed, for example, using a light source capable of UV irradiation. As the light source, for example, an ultra-high pressure UV lamp (eg, an ultra-high pressure mercury lamp) and a UV light emitting diode (UV-LED) can be used.

[0367] The irradiation dose is preferably 10 mJ / cm from the viewpoint of good curing reaction. 2 ~1000mJ / cm 2 range.

[0368] When the curing reaction is carried out by irradiation of UV or the like, from the viewpoint of suppressing the curing hindrance caused by oxygen and further promoting the surface curing of the resin layer, it is preferred to replace the atmosphere of the UV irradiation area with an inert gas (e.g., a monomer) to reduce the oxygen concentration. The oxygen concentration of the atmosphere in the UV irradiation area is preferably 0.01% to 5%.

[0369] Furthermore, from the viewpoint of promoting the curing reaction, it is preferred to increase the temperature of the atmosphere in the UV irradiation region. The temperature of the atmosphere in the UV irradiation region is preferably 25°C to 100°C, more preferably 30°C to 80°C, and even more preferably 40°C to 70°C.

[0370] [Second embodiment of optical material]

[0371] The second embodiment is an optical material having a hard coat layer, a transparent support substrate, and a bonding layer or an adhesive layer laminated in this order.

[0372] Examples of the optical material of the second embodiment include a protective film and a protective sheet.

[0373] In the second embodiment, the specific dye may be contained in any one of the support substrate, hard coat layer, and adhesive layer or bonding layer, or in two or more of the support substrate, hard coat layer, and adhesive layer or bonding layer.

[0374] That is, in the second embodiment, at least one of the supporting substrate, the hard coat layer, and the adhesive layer or the bonding layer is formed using the resin composition or liquid composition of the present invention as described above.

[0375] The second embodiment is preferably a method in which (1) at least the hard coating layer is a cured product of the resin composition or liquid composition of the present invention, or (2) at least the supporting substrate is a cured product of the resin composition or liquid composition of the present invention. The supporting substrate in the case of (1) is synonymous with the first embodiment except that it contains a specific pigment, and the supporting substrate in the case of (2) is a cured product formed using the resin composition or liquid composition of the present invention.

[0376] -Hard coating-

[0377] The second embodiment has a hard coating layer on the supporting substrate.

[0378] When an optical material has a hard coating layer as the outermost layer, the scratch resistance of the optical material can be improved.

[0379] The hard coating layer can be formed by any method of a wet coating method or a dry coating method (vacuum film forming). From the viewpoint of excellent yield, the formation method of the hard coating layer is preferably a wet coating method. When the hard coating layer is formed using the resin composition of the present invention or a liquid composition, it is formed by a wet coating method.

[0380] When the hard coat layer is not a cured product of the resin composition or liquid composition of the present invention, as the hard coat layer, for example, Japanese Patent Application Laid-Open No. 2013-45045, Japanese Patent Application Laid-Open No. 2013-43352, Japanese Patent Application Laid-Open No. 2012-232459, Japanese Patent Application Laid-Open No. 2012-128157, Japanese Patent Application Laid-Open No. 2011-131409, Japanese Patent Application Laid-Open No. 2011-131404, Japanese Patent Application Laid-Open No. 2011-126162, Japanese Patent Application Laid-Open No. 2011-75705, Japanese Patent Application Laid-Open No. 2009-286981 can be applied. The hard coating layer described in the Gazette, Japanese Patent Application Publication No. 2009-263567, Japanese Patent Application Publication No. 2009-75248, Japanese Patent Application Publication No. 2007-164206, Japanese Patent Application Publication No. 2006-96811, Japanese Patent Application Publication No. 2004-75970, Japanese Patent Application Publication No. 2002-156505, Japanese Patent Application Publication No. 2001-272503, International Publication No. 12 / 018087, International Publication No. 12 / 098967, International Publication No. 12 / 086659, and International Publication No. 11 / 105594.

[0381] When the optical material has a hard coat layer, the thickness of the hard coat layer is preferably 5 μm to 100 μm from the viewpoint of further improving the scratch resistance of the optical material.

[0382] - Adhesive layer and bonding layer -

[0383] The second embodiment is an optical material having a bonding layer or an adhesive layer on the side of the supporting substrate opposite to the side having the hard coat layer.

[0384] The type of the binder or adhesive used in the adhesive layer or bonding layer is not particularly limited.

[0385] 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 acid monomer (so-called (meth)acrylic acid polymer).

[0386] Examples of the adhesive include polyurethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives, and silicone adhesives. Among them, polyurethane resin adhesives and silicone adhesives are preferred because of their high bonding strength.

[0387] The adhesive may be a commercially available product, and examples of commercially available products include a polyurethane resin adhesive (trade name: LIS-073-50U) from TOYO INK CO., LTD. For example, a curing agent (trade name: CR-001) from TOYO INK CO., LTD. may be used in combination with the adhesive.

[0388] When the optical material has a bonding layer or an adhesive layer, the thickness of the bonding layer or the adhesive layer is preferably 5 μm to 100 μm from the viewpoint of achieving both bonding strength and handling properties.

[0389] Example

[0390] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples unless it exceeds the gist of the present invention.

[0391] (Example 1): Synthesis Example (Synthesis of D-13)

[0392] [Chemical formula 17]

[0393]

[0394] According to the above scheme, 5.0 g of 1,2-diphenylpyrazolidine-3,5-dione, 3.2 g of indole-3-carboxaldehyde, 0.3 g of ammonium acetate and 70 ml of methanol were added and heated under reflux for 2 hours. After the reaction was completed, the reactant was cooled to room temperature (i.e., 25° C.), the precipitated solid was filtered and washed with methanol, thereby obtaining 6.6 g of compound D-13 (yield 87%).

[0395] The results of confirming the structure of compound D-13 by NMR (nuclear magnetic resonance) are shown below.

[0396] 1 H-NMR (CDCl3): δ9.86 (s, 1H), 9.64 (s, 1H), 8.56 (s, 1H), 7.97 (d, 1H), 7.50~7.46 (m, 4H), 7.39~7.37 (m, 7H), 7.31~7.14 (m, 2H)

[0397] The obtained compound D-13 was dissolved in ethyl acetate, and the maximum absorption wavelength (λmax) and the molar absorption coefficient (ε) were measured using a spectrophotometer UV-1800PC (manufactured by SHIMADZU CORPORATION) using a colorimetric cell with an optical path length of 10 mm.

[0398] As a result, the maximum absorption wavelength (λmax) of compound D-13 was 421 nm, and the molar absorption coefficient (ε) was 41,400.

[0399] (Example 2): Synthesis Example (Synthesis of D-14)

[0400] [Chemical formula 18]

[0401]

[0402] In the synthesis of compound D-13 of Example 1, a reaction was carried out in the same manner as in the synthesis of compound D-13 except that indole-3-carboxaldehyde was changed to methyl 2-(3-formyl-1H-indol-1-yl)propionate, thereby obtaining compound D-14.

[0403] The results of confirming the structure of compound D-14 by NMR are shown below.

[0404] 1 H-NMR (CDCl3): δ9.90 (s, 1H), 8.52 (s, 1H), 8.01~7.99 (m, 1H), 7.47~7.31 (m, 11H), 7.18~7.13(m, 2H), 5.25~5.22(m, 1H), 3.73(s, 3H), 1.98(d, 3H)

[0405] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound D-14 were measured by the same method as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 1 below.

[0406] (Example 3): Synthesis Example (Synthesis of D-24)

[0407] [Chemical formula 19]

[0408]

[0409] In the synthesis of compound D-13 in Example 1, compound D-24 was obtained by performing the same reaction as compound D-13 except that 1,2-diphenylpyrazolidine-3,5-dione was changed to 1,2-dibutylpyrazolidine-3,5-dione.

[0410] The results of confirming the structure of compound D-24 by NMR are shown below.

[0411] 1H-NMR (CDCl3): δ9.76 (s, 1H), 9.30 (s, 1H), 8.33 (s, 1H), 7.96~7.95 (m, 1H), 7.48~7.47 (m, 1 H), 7.35~7.33(m, 2H), 3.41(t, 4H), 1.67~1.65(m, 4H), 1.35~0.31(m, 4H), 0.95~0.91(m, 6H)

[0412] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound D-24 were measured by the same method as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 1 below.

[0413] (Example 4): Synthesis Example (Synthesis of D-4)

[0414] [Chemical formula 20]

[0415]

[0416] In the synthesis of compound D-13 in Example 1, compound D-4 was obtained by reacting in the same manner as compound D-13 except that indole-3-carboxaldehyde was replaced with intermediate 1 (synthesized by the method described in Japanese Patent No. 2707371).

[0417] The results of confirming the structure of compound D-4 by NMR are shown below.

[0418] 1 H-NMR (CDCl3): δ8.23 (d, 2H), 8.09 (s, 1H), 7.82 (s, 1H), 7.46~7.44 (m, 4H), 7.35~7.3 0(m, 6H), 7.17~7.12(m, 2H), 4.46~4.41(m, 2H), 2.30(s, 3H), 2.01(s, 3H), 1.43(t, 3H)

[0419] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound D-4 were measured by the same method as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 1 below.

[0420] (Example 5): Synthesis Example (Synthesis of D-10)

[0421] [Chemical formula 21]

[0422]

[0423] In the synthesis of compound D-4 in Example 4, compound D-10 was obtained by conducting a reaction in the same manner as compound D-4 except that 1,2-diphenylpyrazolidine-3,5-dione was changed to 1,2-dibutylpyrazolidine-3,5-dione.

[0424] The results of confirming the structure of compound D-10 by NMR are shown below.

[0425] 1 H-NMR (CDCl3): δ8.21 (d, 2H), 7.86 (s, 1H), 7.78 (s, 1H), 7.29 (s, 1H), 4.44~4.41 (m, 2H), 3.67-3.66 (m, 4 H), 2.26 (s, 3H), 2.02 (s, 3H), 1.58-1.54 (m, 4H), 1.45-1.41 (m, 3H), 1.36-1.32 (m, 4H), 0.94-0.90 (m, 6H)

[0426] The maximum absorption wavelength (λmax) and molar absorption coefficient (ε) of the obtained compound D-10 were measured by the same method as in Example 1. The measurement results of the maximum absorption wavelength (λmax) and molar absorption coefficient (ε) are shown in Table 1 below.

[0427] [Table 1]

[0428]

[0429] In addition, in the synthesis of compounds D-1 and D-9 in Table 1, the synthesis was carried out by changing the 1,2-diphenylpyrazolidine-3,5-dione and indole-3-carboxaldehyde used in the synthesis of compound D-13 in Example 1 to compounds corresponding to compound D-1 or D-9, respectively, and performing the reaction in the same manner as in Example 1.

[0430] (Example 6): Resin composition

[0431] A resin solution (i.e., a resin composition) was prepared by dissolving 5.4 mg of compound D-1, 7.6 g of chloroform, and 1.1 g of a commercially available polymethyl methacrylate resin (Dianal BR-80 (a PMMA-based polymer containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw: 95,000, acid value: 0 mgKOH / g), manufactured by Mitsubishi Chemical Corporation). Then, the prepared resin solution was spin-coated on a glass substrate, and the coated film was dried at 40° C. for 2 minutes to form a resin film having a thickness of 10 μm containing compound D-1.

[0432] (Examples 7 to 12): Resin composition

[0433] In Example 6, a resin film was formed in the same manner as in Example 6 except that Compound D-1 was changed to a dye (ie, a specific dye) shown in Table 2 below.

[0434] (Comparative Example 1): Resin composition

[0435] In Example 6, a resin film was formed in the same manner as in Example 6 except that the compound D-1 was changed to the comparative dye E-1 described below.

[0436] [Chemical formula 22]

[0437]

[0438] (evaluate)

[0439] -1. Heat resistance-

[0440] For the resin films formed in Examples 6 to 12 and Comparative Example 1, the maintenance rate of absorbance at λmax (maximum absorption wavelength; nm) was determined under the following conditions 1 and 2 as an index for evaluating heat resistance. The maintenance rate of absorbance is shown in Table 2. In addition, the greater the maintenance rate of absorbance, the better the heat resistance. The resin film was irradiated with light of wavelength λmax using a spectrophotometer UV-1800PC (manufactured by SHIMADZU CORPORATION), and the absorbance was determined based on the transmittance of the light.

[0441] (Condition 1)

[0442] After measuring the absorbance of the resin film at λmax, the resin film was heated at 80°C for 1 hour (h) and the absorbance at λmax after heating was measured. The absorbance maintenance rate (%) was calculated from the absorbance values ​​at λmax before and after heating by the following formula.

[0443] Absorbance maintenance rate (%) = (absorbance at λmax after heating / absorbance at λmax before heating) × 100

[0444] (Condition 2)

[0445] The absorbance maintenance rate (%) was calculated in the same manner as in Condition 1 except that the heating conditions of the resin film were changed to 200° C. and 5 minutes.

[0446] -2.Lightfastness-

[0447] For the resin films formed in Examples 6 to 12 and Comparative Example 1, the absorbance maintenance rate at λmax (maximum absorption wavelength; nm) was determined under the following condition 3 as an index for evaluating light resistance.

[0448] Specifically, after measuring the absorbance of the resin film at λmax, the resin film was irradiated under condition 3, and then the absorbance at λmax after 24 hours of irradiation was measured. The absorbance maintenance rate (%) was calculated by the following formula based on the absorbance values ​​at λmax before and after irradiation. The absorbance maintenance rate is shown in Table 2. The resin film was irradiated with light of a wavelength of λmax using a spectrophotometer UV-1800PC (manufactured by SHIMADZU CORPORATION), and the absorbance was calculated from the transmittance of the light.

[0449] Absorbance maintenance rate (%) = (absorbance at λmax after irradiation / absorbance at λmax before irradiation) × 100

[0450] In addition, a larger absorbance maintenance rate indicates better light resistance.

[0451] (Condition 3)

[0452] Equipment: Low temperature cycle xenon lamp weathering tester (product name: XL75, manufactured by Suga Test Instruments Co., Ltd.)

[0453] Illumination: 10klx(40w / m 2 )

[0454] Time: 24 hours

[0455] Environment: 23℃, 5%RH

[0456] Measurement: λmax measurement through a UV cutoff filter with a cutoff wavelength of 320nm or less

[0457] [Table 2]

[0458]

[0459] The seven specific dyes synthesized as described above (ie, the dyes represented by Formula 1) are compounds having a maximum absorption wavelength in the wavelength range of 350 nm to 450 nm and exhibiting UV shielding properties and blue light shielding properties.

[0460] Furthermore, as shown in Table 2, in Examples 6 to 12 using specific pigments, the resin films formed in the form of molded products of the resin compositions were excellent in heat resistance and light resistance. In contrast, in Comparative Example 1 using comparative pigment E-1, the heat resistance and light resistance of the formed resin film were significantly poor.

[0461] Industrial Applicability

[0462] The resin composition and liquid composition of the present invention can be applied to optical materials, such as optical filters (eg, optical lenses) and optical films or optical sheets (including protective sheets).

[0463] Specific examples of optical materials include blue light cutoff materials that block or suppress blue light in the visible light region (e.g., blue light cutoff lenses (e.g., glasses and contact lenses)); UV cutoff materials that block or suppress ultraviolet (UV) rays (e.g., UV cutoff lenses (e.g., glasses and contact lenses), UV cutoff films or UV cutoff sheets (e.g., films for windows, films for displays of various image display devices, and films for displays of portable terminals (smartphones, tablet computers, etc.)), UV cutoff glass (e.g., glass for vehicles and glass for building materials)). The optical material of the present invention is suitable for use, for example, in improving the durability of LCDs and organic EL elements. Among them, the optical material of the present invention is particularly suitable for use in environments requiring heat resistance and light resistance.

[0464] Furthermore, the liquid composition of the present invention and the pigment compound of the present invention are suitable for use in an environment requiring heat resistance and light resistance, and can be suitably used as ink, coating material, and the like.

[0465] Furthermore, the dye compound of the present invention may be added to a binder for use.

[0466] Examples of image display devices include liquid crystal display devices (LCD), plasma display panels, electroluminescence (EL) displays, cathode ray tube display devices, and the like.

[0467] 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.

[0468] The touch panel is not particularly limited and can be appropriately selected according to the purpose. Examples of the touch panel include a surface-type electrostatic capacitive touch panel, a projection-type electrostatic capacitive touch panel, and a resistive film touch panel. In addition, the touch panel includes a so-called touch sensor and a touch pad.

[0469] The entire disclosure of Japanese Patent Application No. 2019-096563 filed on May 23, 2019 is incorporated into this specification by reference.

[0470] All documents, patent applications, and technical standards described in this specification are incorporated by reference into this specification to the same extent as if each document, patent application, and technical standard was specifically and individually described as being incorporated by reference.

Claims

1. A resin composition comprising a pigment represented by the following formula 1 and a resin, In formula 1, R 1 and R 2 are all unsubstituted phenyl groups, or are all unsubstituted alkyl groups having 1 to 12 carbon atoms, or are all unsubstituted benzyl groups, About R 3 , R 5 and R 6 , (i) R 5 With R 6 Bonded to each other to form a 6-membered ring, R 3 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, or (ii) R 3 and R 5 are each independently an unsubstituted alkyl group having 1 to 8 carbon atoms, R 6 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, R 4 is a hydrogen atom, a substituted alkyl group having 1 to 18 carbon atoms in total substituted by an alkoxycarbonyl group, or a substituted aryl group having 6 to 22 carbon atoms in total substituted by an alkoxycarbonyl group, in, When R 4 When it is a hydrogen atom, R 1 and R 2 Each of them is an unsubstituted alkyl group having 1 to 12 carbon atoms.

2. A liquid composition comprising a pigment represented by the following formula 1 and a solvent, In formula 1, R 1 and R 2 are all unsubstituted phenyl groups, or are all unsubstituted alkyl groups having 1 to 12 carbon atoms, or are all unsubstituted benzyl groups, About R 3 , R 5 and R 6 , (i) R 5 With R 6 Bonded to each other to form a 6-membered ring, R 3 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, or (ii) R 3 and R 5 are each independently an unsubstituted alkyl group having 1 to 8 carbon atoms, R 6 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, R 4 is a hydrogen atom, a substituted alkyl group having 1 to 18 carbon atoms in total substituted by an alkoxycarbonyl group, or a substituted aryl group having 6 to 22 carbon atoms in total substituted by an alkoxycarbonyl group, in, When R 4 When it is a hydrogen atom, R 1 and R 2 Each of them is an unsubstituted alkyl group having 1 to 12 carbon atoms.

3. The liquid composition according to claim 2, which is used for ink or coating.

4. A pigment compound represented by the following formula 2: In formula 2, R 1 and R 12 are all unsubstituted phenyl groups, or are all unsubstituted alkyl groups having 1 to 12 carbon atoms, or are all unsubstituted benzyl groups, About R 3 , R 5 and R 6 , (i) R 5 With R 6 Bonded to each other to form a 6-membered ring, R 3 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, or (ii) R 3 and R 5 are each independently an unsubstituted alkyl group having 1 to 8 carbon atoms, R 6 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, R 4 is a hydrogen atom, a substituted alkyl group having 1 to 18 carbon atoms in total substituted by an alkoxycarbonyl group, or a substituted aryl group having 6 to 22 carbon atoms in total substituted by an alkoxycarbonyl group, in, When R 4 When it is a hydrogen atom, R 1 and R 12 Each of them is an unsubstituted alkyl group having 1 to 12 carbon atoms. 5 . An optical material, which is a cured product of the resin composition according to claim 1 or the liquid composition according to claim 2 or 3.

6. An optical material comprising a pigment represented by the following formula 1, In formula 1, R 1 and R 2 are all unsubstituted phenyl groups, or are all unsubstituted alkyl groups having 1 to 12 carbon atoms, or are all unsubstituted benzyl groups, About R 3 , R 5 and R 6 , (i) R 5 With R 6 Bonded to each other to form a 6-membered ring, R 3 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, or (ii) R 3 and R 5 are each independently an unsubstituted alkyl group having 1 to 8 carbon atoms, R 6 represents a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, or an unsubstituted aryl group having 6 to 10 carbon atoms, R 4 is a hydrogen atom, a substituted alkyl group having 1 to 18 carbon atoms in total substituted by an alkoxycarbonyl group, or a substituted aryl group having 6 to 22 carbon atoms in total substituted by an alkoxycarbonyl group, in, When R 4 When it is a hydrogen atom, R 1 and R 2 Each of them is an unsubstituted alkyl group having 1 to 12 carbon atoms. The optical material according to claim 5 or 6, which is a spectacle lens. The optical material according to claim 5 or 6, which is a protective sheet.

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