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

Abstract

The present invention provides a compound represented by general formula (1), a dye, and an application thereof. In general formula (1), R1, R2, and R5 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and R3 and R4 each independently represent an alkyl group, an aryl group, or a heterocyclic group.

Description

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

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

[0002] Dyes with a small half-width that selectively absorb light having a wavelength near 580 nm are useful for improving the optical properties of various optical components, such as displays, optical filters, eyeglass lenses, and contact lenses. Known dyes that selectively absorb light having a wavelength near 580 nm include dyes having a squarylium skeleton. For example, squarylium compounds that absorb light in the 530 nm to 580 nm wavelength range have been proposed, with the objective of providing optical filters that improve the color purity of displays and the like (see International Publication No. 2005 / 021249). Furthermore, squarylium compounds having a specific aminothiazole structure have been disclosed as colorants that can be used in combination with silicon phthalocyanine compounds used in electronic toners, which are known to have good color reproducibility (see International Publication No. 2011 / 055647).

[0003] However, according to studies by the present inventors, the squarylium compounds described in WO 2005 / 021249 and WO 2011 / 055647 both have insufficient heat resistance. The inventors have found that insufficient heat resistance can cause a problem in that, for example, when the compound is used in a display that is used for a long period of time in close proximity to a light source, the color tone changes over time.

[0004] An object of one embodiment of the present disclosure is to provide a novel compound or a method for producing the novel compound.An object of another embodiment of the present disclosure is to provide a dye having good moist heat resistance, a composition containing the dye, an optical filter, a spectacle lens, or a contact lens containing the novel compound.

[0005] The means for solving the above problems include the following aspects.

[0006] <1> A compound represented by the following general formula (1):

[0007]

[0008] In general formula (1), R １ , R ２ , and R ５ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ and R ４ each independently represents an alkyl group, an aryl group, or a heterocyclic group. ３ <3> The compound according to <1>, wherein R in general formula (1) is an alkyl group. ３ The compound according to <1> or <2>, wherein

[0009] <4> A dye which is the compound according to any one of <1> to <3>. <5> A composition comprising the compound according to any one of <1> to <3> and a resin. <6> A composition comprising the compound according to any one of <1> to <3>, a monomer, and a polymerization initiator.

[0010] <7> An optical filter comprising the compound according to any one of <1> to <3>. <8> A spectacle lens comprising the compound according to any one of <1> to <3>. <9> A contact lens comprising the compound according to any one of <1> to <3>.

[0011] <10> A method for producing a compound represented by the following general formula (1), using a compound represented by the following general formula (2):

[0012]

[0013] In general formula (2), R １ , and R ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ represents an alkyl group, an aryl group, or a heterocyclic group.

[0014]

[0015] In general formula (1), R １ , R ２ , and R ５ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ and R ４ each independently represents an alkyl group, an aryl group, or a heterocyclic group.

[0016] Preferred embodiments of the present disclosure are as follows: R in general formula (1) ３ The dye according to <4>, wherein R in general formula (1) is an alkyl group. ３ <C> A composition comprising the dye according to <4> and a resin. <D> A composition comprising the dye according to <4>, a monomer, and a polymerization initiator. <E> An optical filter comprising the dye according to <4>. <F> A spectacle lens comprising the dye according to <4>. <G> A contact lens comprising the dye according to <4>.

[0017] According to one embodiment of the present disclosure, there is provided a novel compound or a method for producing the novel compound. According to another embodiment of the present disclosure, there is provided a dye having good moist heat resistance, a composition containing the dye, an optical filter, a spectacle lens, or a contact lens containing the novel compound.

[0018] The contents of the present disclosure are described in detail below. These descriptions and examples are intended to illustrate embodiments of the present disclosure and do not limit the scope of the embodiments. In the present disclosure, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in the present disclosure, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit value of that numerical range may be replaced with the value shown in the examples. In the present disclosure, a combination of two or more preferred aspects is a more preferred aspect.

[0019] In the present disclosure, "total solid content" refers to the total mass of components excluding the solvent from the entire composition. Furthermore, as described above, "solid content" refers to components excluding the solvent, and may be, for example, a solid or liquid at 25°C. In the notation of groups (atomic groups) in the present disclosure, notations that do not specify whether they are substituted or unsubstituted encompass both unsubstituted and substituted groups. For example, "alkyl group" encompasses not only alkyl groups without substituents (unsubstituted alkyl groups) but also alkyl groups with substituents (substituted alkyl groups). In the present disclosure, "(meth)acrylate" refers to both or either acrylate and methacrylate, "(meth)acrylic" refers to both or either acrylic and methacrylic, and "(meth)acryloyl" refers to both or either acryloyl and methacryloyl.

[0020] In this specification, the weight average molecular weight and number average molecular weight of a resin are defined as polystyrene equivalent values ​​measured by gel permeation chromatography (GPC). In this disclosure, when the content of "structural units" in a resin is defined by a molar ratio, "structural units" are synonymous with "monomer units." However, in this disclosure, "monomer units" may be modified after polymerization by a polymer reaction or the like. "Room temperature" refers to an ambient temperature that is not specifically temperature-controlled, and in this disclosure, refers to "25°C" unless otherwise specified.

[0021] <Compound> The compound of the present disclosure is a novel compound, which is a compound represented by the following general formula (1) (hereinafter, also simply referred to as "specific compound (1)").

[0022]

[0023] In general formula (1), R １ , R ２ , and R ５ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ and R ４ each independently represents an alkyl group, an aryl group, or a heterocyclic group.

[0024] R １ , R ２ , R ３ , R ４ , or R ５ When R represents an alkyl group, the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and even more preferably 1 to 8 carbon atoms. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group. Specific examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group. １ , R ２ , R３ , R ４ , or R ５ The alkyl group represented by is preferably a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

[0025] R １ , R ２ , R ３ , R ４ , or R ５ When R represents an aryl group, the aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms. The aryl group may have a substituent as described below. Specific examples of the aryl group include a phenyl group, a 2,6-diethylphenyl group, a 3,5-ditrifluoromethylphenyl group, a styryl group (vinylphenyl group), a naphthyl group, and a biphenyl group. １ , R ２ , R ３ , R ４ , or R ５ The aryl group represented by is preferably a phenyl group.

[0026] R １ , R ２ , R ３ , R ４ , or R ５ When R represents a heterocyclic group, the heterocyclic group is preferably a heterocyclic group having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Examples of the heterocyclic group include heterocyclic groups having a heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom. The heterocyclic group may have a substituent as described below. Specific examples of the heterocyclic group include an epoxy group, an oxetanyl group, an imidazolyl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a piperidyl group, a morpholino group, a benzoxazolyl group, a benzimidazolyl group, and a benzthiazolyl group. １ , R ２ , R ３ , R ４ , or R ５ The heterocyclic group represented by is preferably a pyridyl group.

[0027] R １ , R２ , R ３ , R ４ , and R ５ Each substituent represented by may be further substituted by a substituent. When two or more substituents are present, the plurality of substituents may be the same or different. If possible, they may be bonded to each other to form a ring, for example, R １ , and R ２ may be linked to form a ring with or without a linking group.

[0028] In the above description of "may be further substituted with a substituent," the type, position, and number of substituents are not particularly limited. The number of substituents introduced may be, for example, one, two, three, or more. Examples of substituents include monovalent non-metallic atomic groups excluding hydrogen atoms, which can be selected, for example, from the following substituent group Y:

[0029] (Substituent Group Y) Substituent Group Y includes halogen atoms (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom); mercapto group; cyano group; carboxy group; phosphate group; sulfo group; hydroxy group; carbamoyl groups having 1 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and more preferably 2 to 5 carbon atoms (e.g., hydroxycarbamoyl group, methylcarbamoyl group, ethylcarbamoyl group, morpholinocarbamoyl group); sulfamoyl groups having 0 to 10 carbon atoms, preferably 2 to 8 carbon atoms, and more preferably 2 to 5 carbon atoms (e.g., methylsulfamoyl group, ethylsulfamoyl group, group, piperidinosulfamoyl group); a nitro group; an alkyl group having 1 to 30 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methyl group, ethyl group, propyl group, butyl group, t-butyl group, i-butyl group, s-butyl group, pentyl group, t-pentyl group, hexyl group, heptyl group, octyl group, hydroxymethyl group, trifluoromethyl group, benzyl group); a cycloalkyl group having 3 to 30 carbon atoms, preferably 4 to 12 carbon atoms, and more preferably 5 to 8 carbon atoms (e.g., cyclohexyl group, 4-methylcyclohexyl group, 4- alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methoxy, ethoxy, 2-methoxyethoxy, 2-phenylethoxy); aryloxy groups having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms (e.g., phenoxy, p-methylphenoxy, p-chlorophenoxy, naphthoxy); aryloxy groups having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (e.g., phenyl, p-methylphenoxy, p-chlorophenoxy, naphthoxy); acyl groups having 2 to 8 carbon atoms (e.g., acetyl, benzoyl, trichloroacetyl); acyloxy groups having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (e.g., acetyloxy, benzoyloxy); acylamino groups having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (e.g., acetylamino); sulfonyl groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methanesulfonyl, ethanesulfonyl, benzenesulfonyl);Sulfinyl groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methanesulfinyl, ethanesulfinyl, and benzenesulfinyl groups); sulfonylamino groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms (e.g., methanesulfonylamino, ethanesulfonylamino, and benzenesulfonylamino groups); amino groups having 0 to 20 carbon atoms, preferably 0 to 12 carbon atoms, and more preferably 0 to 8 carbon atoms (e.g., unsubstituted amino groups, methylamino groups, dimethylamino groups, and benzylamino groups); group, anilino group, diphenylamino group); ammonium groups having 0 to 15 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms (e.g., trimethylammonium group, triethylammonium group); hydrazino groups having 0 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms (e.g., trimethylhydrazino group); ureido groups having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms (e.g., ureido group, N,N-dimethylureido group); 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 carbon atom imido groups having 1 to 6 carbon atoms (for example, succinimido groups); alkylthio groups having 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 8 carbon atoms (for example, methylthio groups, ethylthio groups, and propylthio groups); arylthio groups having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms (for example, phenylthio, p-methylphenylthio, p-chlorophenylthio, 2-pyridylthio, and naphthylthio); alkoxycarbonyl groups having 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms (for example, methoxycarbonyl groups). , ethoxycarbonyl group, 2-benzyloxycarbonyl group); aryloxycarbonyl groups having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms (for example, phenoxycarbonyl group); aryl groups having 6 to 20 carbon atoms, preferably 6 to 15 carbon atoms, and more preferably 6 to 10 carbon atoms (for example, phenyl, naphthyl, p-carboxyphenyl, p-nitrophenyl, 3,5-dichlorophenyl, p-cyanophenyl, m-fluorophenyl, p-tolyl, p-cyclohexylphenyl, p-(4-pentylcyclohexyl)phenyl);Substituted or unsubstituted heterocyclic groups having 1 to 20 carbon atoms, preferably 2 to 10 carbon atoms, and more preferably 4 to 6 carbon atoms (e.g., pyridyl, 5-methylpyridyl, thienyl, furyl, morpholino, and tetrahydrofurfuryl); and when these substituents can further have one or more substituents, the further substituents can include the group consisting of groups having a substituent selected from the above-mentioned substituents;

[0030] Preferred examples of the substituent that can be introduced include an alkyl group, an aryl group (e.g., a phenyl group), a heterocyclic group, an alkoxy group, an aryloxy group, a halogen atom (e.g., a fluorine atom), an amino group, a hydroxy group, a sulfo group, a carboxy group, an oxycarbonyl group, an acylamino group, an alkoxycarbonyl group, an aryloxycarbonylamino group, a sulfonylamino group, a carbamoyl group, an alkylthio group, an arylthio group, a sulfonyl group, a cyano group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, an azo group, and a silyl group.

[0031] R in general formula (1) ３ represents an alkyl group, an aryl group, or a heterocyclic group, and among these, from the viewpoint of the stability of the compound, R ３ is preferably an alkyl group or an aryl group, and more preferably an alkyl group. ３ is particularly preferably a tertiary alkyl group. The tertiary alkyl group is preferably a tertiary alkyl group having 4 to 10 carbon atoms, and more preferably a tertiary alkyl group having 4 to 8 carbon atoms. Examples of the tertiary alkyl group include a tert-butyl group and a tert-pentyl group, and from the viewpoint of the stability of the compound, a tert-butyl group is preferred.

[0032] <Dye> The compound represented by general formula (1) is useful as a dye. The dye of the present disclosure is a compound represented by the above-described general formula (1). The dye of the present disclosure, which is a compound represented by general formula (1), preferably has a maximum absorption wavelength at a wavelength of around 580 nm, specifically, at a wavelength of 550 nm to 590 nm, and more preferably has a maximum absorption wavelength at a wavelength of 560 nm to 585 nm.

[0033] The dye of the present disclosure has good resistance to moist heat. The mechanism of this action is not clear, but in general formula (1), R ３ The presence of an alkyl group, an aryl group or a heterocyclic group at the position of R is stabilized, and preferably a bulky alkyl group, an aryl group or a heterocyclic group is present, which can prevent R from being attacked by nucleophilic attack, particularly when the R comes into contact with water. ３ It is believed that this is because the substituents in the compound are unlikely to be eliminated, resulting in a stable compound. Because the compound is stable, the dye of the present disclosure has good resistance to moist heat and is unlikely to discolor due to temperature or humidity. Note that the above-mentioned mechanism of action is only a hypothesis, and does not limit the effects of the present disclosure.

[0034] Specific examples (exemplary compounds) of the compounds and dyes of the present disclosure are listed below. However, the compounds and dyes of the present disclosure are not limited to the exemplary compounds shown below. Note that exemplary compounds S-1 to S-14 are compounds represented by the formula (1) below, where R １ , R ２ , R ３ , R ４ , and R ５ are shown in the table below. S-15 and S-16 indicate their structures. In the chemical formulas below, the substituents Me represent a methyl group, Et represent an ethyl group, i-Pr represent an isopropyl group, n-Pr represent a normal propyl group, t-Bu represent a tert-butyl group, and Ph represent a phenyl group.

[0035]

[0036]

[0037]

[0038] The maximum absorption wavelength and absorbance of each of the above exemplary compounds were measured by the following method, and all of them had a maximum absorption wavelength in the wavelength range of 550 nm to 580 nm and an absorbance of 0.60 or more, making them useful compounds as dyes. ３However, alkyl groups, particularly bulky tertiary alkyl groups such as Compounds S-3, S-6, S-8, and S-11, are preferred from the viewpoint of higher resistance to moist heat, and R ４ and R ５ Compounds S-3 and S-6 further having a tertiary alkyl group are more preferred.

[0039] (Measurement of maximum absorption wavelength and absorbance) For each example compound, 3.0 × 10 －５ The sample solution is diluted with chloroform to a concentration of 1000 mol / L, and the absorbance of the resulting sample solution is measured in a 1 mm quartz cell using a spectrophotometer (UV-3600 Plus, manufactured by Shimadzu Corporation). The maximum absorption wavelength (λmax) is measured from the absorption spectrum of the sample solution.

[0040] <Method for producing compound> There are no particular limitations on the method for producing the compound or dye of the present disclosure, but it is preferable that they are produced by the method for producing the compound of the present disclosure (hereinafter also referred to as the production method of the present disclosure) shown below. The production method of the present disclosure is a method for producing the compound represented by the above general formula (1) using a compound represented by the following general formula (2).

[0041]

[0042] In general formula (2), R １ , and R ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ represents an alkyl group, an aryl group, or a heterocyclic group.

[0043] An example of a synthesis scheme for the production method of the present disclosure will be given below.

[0044]

[0045] In the production method of the present disclosure, the compound represented by the above general formula (2) is used as a starting material, and thus R ３ The R ３ ​This method allows efficient and stable production of compounds having an alkyl group, an aryl group, or a heterocyclic group at the end. Examples of compounds represented by general formula (2) include 4-alkyl-2-dialkylaminothiazoles and 4-phenyl-2-dialkylaminothiazoles. Specific synthesis methods will be described in detail in the Examples.

[0046] The dye of the present disclosure has good moist heat resistance, and considering the maximum absorption wavelength, absorbance, etc., it can be suitably used in optical products such as optical filters, eyeglass lenses, and contact lenses. Because the dye of the present disclosure has good moist heat resistance, it can be suitably used for various applications as a composition containing other components. The compound of the present disclosure or a dye that is a compound of the present disclosure can be suitably used, for example, in a composition containing a resin, a polymerizable composition, etc.

[0047] <Composition: First Aspect> The first aspect of the composition of the present disclosure includes the dye and a resin described above. There are no particular limitations on the resin used in the first aspect of the composition of the present disclosure. Considering the characteristics of the dye, suitable examples include resins contained in optical filters. From the above perspective, the resin is preferably a resin capable of forming a film or light-absorbing layer with excellent transparency and mechanical properties. Examples of such resins include polyesters such as polyethylene terephthalate; cellulose esters such as cellulose diacetate, cellulose triacetate, and cellulose acetate butyrate; polyolefins such as polyethylene and polypropylene; polyvinyl chloride, polyvinylidene chloride, vinyl chloride-vinyl acetate copolymers, and polystyrene; acrylic addition polymers such as polymethyl methacrylate; polycarbonates made of polycarbonate esters; and known resins such as gelatin. Among these, polyesters, cellulose esters, and gelatin are preferred as the resin from the standpoints of cost, film quality, and transparency. Furthermore, when the optical filter is a laminate having a light-absorbing layer (e.g., a blue light-absorbing layer) formed on a substrate from a composition containing a resin and the dye of the present disclosure, it is preferable to use a resin that has excellent adhesion to the substrate. Examples of resins that have excellent adhesion to the substrate include polymethyl methacrylate, cellulose acetate butyrate, and polycarbonate.

[0048] When the composition of the present disclosure is used for eyeglass lenses described below, there are no particular limitations on the resin as long as it satisfies the physical properties required for eyeglass lenses, such as transparency, refractive index, processability, and hardness after curing. When the composition of the present disclosure is used for eyeglass lenses, the resin may be a thermoplastic resin or a thermosetting resin. Examples of thermoplastic resins that can be used for eyeglass lenses include polycarbonate (PC). Examples of thermosetting resins include urethane resins and episulfide resins. As urethane resins, thiourethane resins are preferred. As resins, thiourethane resins are preferred from the viewpoint of their high refractive index, and polycarbonate resins are preferred from the viewpoint of their good transparency.

[0049] From the viewpoint of film strength and uniformity, the resin that can be contained in the composition of the present disclosure preferably has a weight-average molecular weight in the range of 10,000 to 1,000,000, and more preferably in the range of 20,000 to 500,000. The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin in the present disclosure are values ​​measured by gel permeation chromatography (GPC) under the following conditions. [Solvent] Tetrahydrofuran [Apparatus] TOSOH HLC-8220GPC (Tosoh Corporation) [Column] Three TOSOH TSKgel Super HZM-H columns (4.6 mm x 15 cm) were used in conjunction. [Column temperature] 25°C [Sample concentration] 0.1% by mass [Flow rate] 0.35 ml / min [Calibration curve] A calibration curve was used using seven samples of TSK standard polystyrene manufactured by TOSOH, with Mw = 2,800,000 to 1,050.

[0050] The resin suitable for the optical filter includes, for example, resins suitable for eyeglass lenses and contact lenses, which will be described later, and can be selected depending on the purpose.

[0051] The content of the dye of the present disclosure in the first aspect of the composition can be appropriately selected depending on the intended use of the composition. For example, the content of the dye of the present disclosure relative to the total solid content of the composition can be in the range of 0.001% by mass to 50% by mass, preferably in the range of 0.1% by mass to 10% by mass. Furthermore, the content of the resin relative to the total solid content of the composition can be in the range of 1% by mass to 99.99% by mass, preferably in the range of 10% by mass to 99.99% by mass.

[0052] <Composition: Second Aspect> A second aspect of the composition of the present disclosure includes the dye, monomer, and polymerization initiator of the present disclosure. According to the studies of the present inventors, it has been found that the dye of the present disclosure has good radical resistance in addition to moist heat resistance. This is because R ３ When R is an alkyl group, particularly a tertiary alkyl group, ３This is thought to be because radical elimination is less likely to occur in the substituent located at position 1 than in, for example, an alkoxy group, etc. Therefore, the dye of the present disclosure has the advantage that the dye maintains its stability and is less likely to discolor even in a curable composition containing a monomer and a polymerization initiator, i.e., the second aspect of the composition of the present disclosure.

[0053] As the monomer that can be included in the second aspect of the composition of the present disclosure, a known monomer having a polymerizable group (i.e., a polymerizable monomer) can be selected and used depending on the purpose. The polymerizable monomer may be a radical polymerizable monomer or a cation polymerizable monomer, but a radical polymerizable monomer is preferred because the dye of the present disclosure has radical resistance. Examples of the radical polymerizable monomer include compounds having one or more ethylenically unsaturated bonds in the molecule.

[0054] The molecular weight of the monomer that can be used in the second aspect of the composition of the present disclosure, i.e., the polymerizable monomer, is preferably less than 2,000, more preferably 1,500 or less. The lower limit of the molecular weight of the monomer is preferably 100 or more, more preferably 200 or more. The compound having an ethylenically unsaturated group as the polymerizable monomer is preferably a trifunctional to 15-functional (meth)acrylate compound, more preferably a trifunctional to hexafunctional (meth)acrylate compound. Specific examples of the compound having an ethylenically unsaturated group include the compounds described in paragraph 0128 of WO 2022 / 085485 and the compounds described in JP 2017-194662 A, the contents of which are incorporated herein by reference. More specific examples of the polymerizable monomer include 2-hydroxyethyl methacrylate, methyl methacrylate, butyl acrylate, 2-hydroxyethyl acrylate, benzyl methacrylate, etc.

[0055] As the compound having an ethylenically unsaturated group, the compounds described in paragraphs 0129 to 0137 of WO 2022 / 085485 can also be used. The compound having an ethylenically unsaturated group may be a compound having an acid group such as a carboxy group, a sulfo group, or a phosphate group, a compound having a caprolactone structure, a compound having an alkyleneoxy group, or a compound having a fluorene skeleton.

[0056] As the compound having an ethylenically unsaturated group, it is also preferable to use U-108A, UA-112P, UA-7100 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (all manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), and the like.

[0057] The content of the monomer is preferably 0.1% by mass to 50% by mass relative to the total solid content contained in the composition of the second aspect of the present disclosure. The lower limit is more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit is more preferably 45% by mass or less, and even more preferably 40% by mass or less. In the second aspect of the composition of the present disclosure, only one type of monomer may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is in the above range.

[0058] As the polymerization initiator that can be included in the second aspect of the composition of the present disclosure, a known polymerization initiator can be selected and used depending on the purpose. The polymerization initiator may be a thermal polymerization initiator or a photopolymerization initiator. Since the compound of the present disclosure has good radical resistance, the second aspect of the composition of the present disclosure can be a polymerizable composition that includes a radical polymerization initiator as the polymerization initiator.

[0059] Radical polymerization initiators that can be used in the second aspect of the composition of the present disclosure include oxime compounds, α-aminoacetophenone compounds, α-hydroxyketone compounds, acylphosphine compounds, and organic peroxides. Of these, oxime compounds are preferred as radical polymerization initiators. By using the radical polymerization initiator represented by Formula 1 above in combination with another radical polymerization initiator, a more balanced pattern with good rectangularity can be obtained.

[0060] Examples of oxime compounds include the compounds described in paragraph 0142 of WO 2022 / 085485, the polymers described in JP 2020-172619 A, the compounds represented by formula 1 described in WO 2020 / 152120, and the oxime ester compounds described in WO 2021 / 023144. Specific examples of oxime compounds and commercially available products include the compounds described in paragraph 0142 of WO 2022 / 085485. Commercially available products include TR-PBG-327 (manufactured by Tronley). It is also preferable to use a compound that is not colorable or that is highly transparent and resistant to discoloration as the oxime compound. Commercially available products include ADEKA ARCLES NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA Corporation). Other radical polymerization initiators include fluorenyl amino ketone photoinitiators described in JP-A-2020-507664, photopolymerization initiators represented by the general formula (1) of JP-A-2021-173858, photopolymerization initiators described in paragraphs 0022 to 0024 of JP-A-2021-173858, photopolymerization initiators represented by the general formula (1) of JP-A-2021-170089, photopolymerization initiators described in paragraphs 0117 to 0120 of JP-A-2021-170089, and JP-A-2021 -181406 compounds described in JP-A-2022-013379 photopolymerization initiators described in JP-A-2022-015747 compounds represented by formula (1), fluorine-containing fluorene oxime ester photoinitiators described in JP-T-2021-507058, initiators described in Chinese Patent Application Publication No. 110764367, initiators described in JP-T-2022-518535, initiators described in WO 2021 / 175855, etc. can also be used. In addition, as an oxime compound, compounds described in paragraphs 0143 to 0149 of WO 2022 / 085485 can be used.

[0061] Specific examples of the oxime compound include the compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600. When the polymerization initiator contains an acylphosphine oxide compound and a thioxanthone compound, the readability after a transfer test and the readability after a rub test are improved.

[0062] Examples of the acylphosphine oxide compound include monoacylphosphine oxide compounds and bisacylphosphine oxide compounds, with bisacylphosphine oxide compounds being preferred.

[0063] Examples of the monoacylphosphine oxide compound include isobutyryldiphenylphosphine oxide, 2-ethylhexanoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, (2,4,6-trimethylbenzoyl)ethoxyphenylphosphine oxide, o-toluyldiphenylphosphine oxide, p-t-butylbenzoyldiphenylphosphine oxide, 3-pyridylcarbonyldiphenylphosphine oxide, acryloyldiphenylphosphine oxide, benzoyldiphenylphosphine oxide, pivaloylphenylphosphinic acid vinyl ester, acryloyldiphenylphosphine oxide, benzo ... Examples of the diphenylphosphine oxide include dipoylbisdiphenylphosphine oxide, pivaloyldiphenylphosphine oxide, p-toluyldiphenylphosphine oxide, 4-(t-butyl)benzoyldiphenylphosphine oxide, terephthaloylbisdiphenylphosphine oxide, 2-methylbenzoyldiphenylphosphine oxide, versatoyldiphenylphosphine oxide, 2-methyl-2-ethylhexanoyldiphenylphosphine oxide, 1-methyl-cyclohexanoyldiphenylphosphine oxide, pivaloylphenylphosphine acid methyl ester, and pivaloylphenylphosphine acid isopropyl ester.

[0064] Examples of the bisacylphosphine oxide compound include bis(2,6-dichlorobenzoyl)phenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-ethoxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2-naphthylphosphine oxide, and bis(2,6-dichlorobenzoyl). phenyl)-1-naphthylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-chlorophenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,4-dimethoxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)decylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-octylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2, 5-dimethylphenylphosphine oxide, bis(2,6-dichloro-3,4,5-trimethoxybenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichloro-3,4,5-trimethoxybenzoyl)-4-ethoxyphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-4-ethoxyphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2- naphthylphosphine oxide, bis(2-methyl-1-naphthoyl)-4-propylphenylphosphine oxide, bis(2-methyl-1-naphthoyl)-2,5-dimethylphenylphosphine oxide, bis(2-methoxy-1-naphthoyl)-4-ethoxyphenylphosphine oxide, bis(2-chloro-1-naphthoyl)-2,5-dimethylphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide.

[0065] Of these, the acylphosphine oxide compound is preferably bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (product name "Omnirad 819", manufactured by IGM Resins B.V.), 2,4,6-trimethylbenzoyldiphenylphosphine oxide (product name "Omnirad TPO-H", manufactured by IGM Resins B.V.), or (2,4,6-trimethylbenzoyl)ethoxyphenylphosphine oxide (product name "Omnirad TPO-L", manufactured by IGM Resins B.V.).

[0066] Examples of thioxanthone compounds include thioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-dodecylthioxanthone, 2,4-diethylthioxanthone, 2,4-dimethylthioxanthone, 1-methoxycarbonylthioxanthone, 2-ethoxycarbonylthioxanthone, 3-(2-methoxyethoxycarbonyl)thioxanthone, 4-butoxycarbonylthioxanthone, and 1-methyl-2-methyl-2-methylthioxanthone. thioxanthone, 3-butoxycarbonyl-7-methylthioxanthone, 1-cyano-3-chlorothioxanthone, 1-ethoxycarbonyl-3-chlorothioxanthone, 1-ethoxycarbonyl-3-ethoxythioxanthone, 1-ethoxycarbonyl-3-aminothioxanthone, 1-ethoxycarbonyl-3-phenylsulfurylthioxanthone, 3,4-di[2-(2-methoxyethoxy)ethoxycarbonyl]thioxanthone, 1-ethoxycarbonyl-3-phenylsulfurylthioxanthone, thioxanthone, 2-methyl-6-dimethoxymethylthioxanthone, 2-methyl-6-(1,1-dimethoxybenzyl)thioxanthone, 2-morpholinomethylthioxanthone, 2-methyl-6-morpholinomethylthioxanthone, n-allylthioxanthone-3,4-dicarboximide, n-octylthioxanthone-3,4-dicarboximide, N-(1,1,3,3-tetramethylthioxanthone), methylbutyl)thioxanthone-3,4-dicarboximide, 1-phenoxythioxanthone, 6-ethoxycarbonyl-2-methoxythioxanthone, 6-ethoxycarbonyl-2-methylthioxanthone, thioxanthone-2-polyethylene glycol ester, and 2-hydroxy-3-(3,4-dimethyl-9-oxo-9H-thioxanthone-2-yloxy)-N,N,N-trimethyl-1-propanaminium chloride.

[0067] The thioxanthone compound may be a commercially available product, such as the SPEEDCURE series manufactured by Lambson (e.g., SPEEDCURE 7010, SPEEDCURE CPTX, SPEEDCURE ITX, etc.).

[0068] Specific examples of the radical polymerization initiator that can be included in the second aspect of the composition of the present disclosure include phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, and examples of commercially available products include ADEKA ARCLES NCI-730 (ADEKA Corporation).

[0069] The second aspect of the composition of the present disclosure may contain only one type of polymerization initiator, or may contain two or more types. From the viewpoint of sensitivity, the content of the polymerization initiator in the second aspect of the composition is preferably 0.01% by mass to 30% by mass, more preferably 0.05% by mass to 25% by mass, even more preferably 0.1% by mass to 20% by mass, and particularly preferably 1% by mass to 15% by mass, relative to the total solid content of the composition.

[0070] By including a monomer and a polymerization initiator in the composition of the present disclosure, a second aspect of the composition of the present disclosure can be a pattern-forming composition that cures only the areas to which energy is applied by localized application of energy such as patterned exposure. Even in such applications, by including the dye of the present disclosure, fading of the dye is suppressed even if radicals are generated during curing by application of energy, and a cured product with a stable hue can be obtained.

[0071] The content of the dye of the present disclosure in the second aspect of the composition can be appropriately selected depending on the application of the composition. For example, the content of the dye of the present disclosure relative to the total solid content of the composition can be in the range of 0.001% by mass to 50% by mass, preferably in the range of 0.1% by mass to 10% by mass. The content of the monomer relative to the total solid content of the second aspect of the composition can be in the range of 1% by mass to 99.99% by mass, preferably in the range of 10% by mass to 99.99% by mass. Furthermore, the content of the polymerization initiator relative to the total solid content of the second aspect of the composition can be in the range of 0.0001% by mass to 10% by mass, preferably in the range of 0.001% by mass to 5% by mass, relative to the total mass of the monomer.

[0072] (Other Components) The composition of the present disclosure may contain other known components in addition to the dye, resin, monomer, and polymerization initiator described above. Examples of other components include known plasticizers, organic acids, dyes, UV absorbers, antioxidants, and matting agents. For details, please refer to paragraphs

[0062] to

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

[0212] to

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

[0073] The composition of the present disclosure may contain an organic solvent from the viewpoint of moldability and handling. After molding the composition, the organic solvent may be removed by heating or the like.

[0074] The dye of the present disclosure has good resistance to moist heat and can therefore be suitably used in optical applications such as optical filters, eyeglass lenses, and contact lenses.

[0075] <Optical Filter> The optical filter of the present disclosure includes the novel compound of the present disclosure described above. The optical filter of the present disclosure may be obtained from a composition containing a resin in addition to the compound of the present disclosure, or may be obtained from a composition containing a monomer and a polymerization initiator in addition to the compound of the present disclosure.

[0076] The optical filter of the present disclosure can be composed of a film formed from a composition containing the compound of the present disclosure and a resin. The optical filter may be composed solely of a film formed from the composition of the present disclosure, or may be a laminate having an optical filter layer formed from a composition containing the compound of the present disclosure and a resin on a substrate. In the optical filter of the present disclosure, the compound of the present disclosure is preferably contained in an amount of 0.1 to 50 parts by mass, more preferably 0.3 to 5 parts by mass, per 1000 parts by mass of the resin. There are no particular restrictions on the resin that can be used in the optical filter, as long as it functions as an optical filter. Preferably, a resin that can form a film or optical filter layer with excellent transparency and mechanical properties is used. Examples of such resins include polyesters such as polyethylene terephthalate, cellulose esters such as cellulose diacetate, cellulose triacetate, and cellulose acetate butyrate, polyolefins such as polyethylene and polypropylene, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-vinyl acetate copolymers, and polystyrene, acrylic addition polymers such as polymethyl methacrylate, polycarbonates made from polycarbonate esters, and gelatin. From the viewpoints of cost, film quality, and transparency, polyesters, cellulose esters, and acrylic resins are preferred. From the viewpoints of film strength and uniformity, the weight-average molecular weight of the resin is preferably in the range of 10,000 to 1,000,000, and more preferably in the range of 20,000 to 500,000.

[0077] The optical filter of the present disclosure may further contain other components as described above in the composition of the present disclosure. Examples of other components include additives such as radical scavengers, antidegradants, and barbituric acid compounds. When additives are included, the content of the additives is preferably in the range of 1 to 30% by mass relative to the resin.

[0078] -Ultraviolet Absorber- From the viewpoint of improving light resistance, the addition of an ultraviolet absorber to the optical filter of the present disclosure is effective. The ultraviolet absorber is not particularly limited, but examples thereof include substituted or unsubstituted benzoic acid esters such as resorcinol monobenzoate and methyl salicylate, cinnamic acid esters such as 2-oxy-3-butyl methoxycinnamate, benzophenones such as 2,4-dioxybenzophenone, α,β-unsaturated ketones such as dibenzalacetone, coumarins such as 5,7-dioxycoumarin, carbostyrils such as 1,4-dimethyl-7-oxycarbostil, and azoles such as 2-phenylbenzimidazole and 2-(2-hydroxyphenyl)benzotriazole.

[0079] Plasticizers that can be used in the optical filters of the present disclosure are not particularly limited, but examples include polyhydric alcohol polyester compounds (hereinafter also referred to as "polyhydric alcohol ester plasticizers"), polycondensation ester compounds (hereinafter also referred to as "polycondensation ester plasticizers"), and carbohydrate compounds (hereinafter also referred to as "carbohydrate derivative plasticizers"). For polyhydric alcohol ester plasticizers, see paragraphs

[0081] to

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

[0099] to

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

[0123] to

[0140] of the same publication; the contents of these publications are incorporated herein by reference.

[0080] (Thickness) The thickness of the optical filter of the present disclosure is usually 0.02 mm to 50 mm, but can be designed to a thickness outside this range depending on the application.

[0081] (Transmittance) The optical filter of the present disclosure only needs to have a transmittance in the wavelength range that it is to block functionally low enough to achieve the intended purpose, and from this viewpoint, the optical filter preferably has a light transmittance of 50% or less, more preferably 20% or less, and even more preferably 10% or less, at 580 nm, for example. Means for achieving the desired transmittance include adjusting the amount of the dye of the present disclosure added to the resin or adjusting the thickness of the optical filter.

[0082] The method for producing the optical filter of the present disclosure is not particularly limited, and the filter can be produced by the following methods. For example, when producing the optical filter, a composition containing the dye and resin of the present disclosure may be melted and extruded by a T-die method or an inflation method, or a composition containing the dye, resin, and organic solvent of the present disclosure may be formed into a film by a casting method.

[0083] As another production method, a polymerizable composition may be prepared by mixing the dye of the present disclosure, a monomer, an organic solvent, and a polymerization initiator, and the polymerizable composition may be applied to a suitable temporary support, polymerized by heat or light, and then formed into a film by peeling off the temporary support.

[0084] When forming an optical filter on a substrate to form a laminate, a method of coating a solution or dispersion composition obtained by mixing the dye, resin, and organic solvent of the present disclosure onto the substrate and producing the laminate can also be used. The substrate is not particularly limited as long as it functions as an optical filter, and various plastic films or glass plates can be used, for example. A primer layer may be formed between the substrate and the optical filter layer to improve adhesion between the substrate and the optical filter layer. Furthermore, a protective layer may be formed on the optical filter layer for the purposes of protecting the optical filter layer, imparting drip resistance, etc. The protective layer can be formed, for example, by superimposing a 0.05 mm thick polyvinyl chloride film on the optical filter layer and heating and pressing it at 120°C to 140°C.

[0085] (Uses) The uses of the optical filter of the present disclosure are not particularly limited, but since the dye of the present disclosure has excellent resistance to moist heat, it can be preferably used, for example, as a color filter for a liquid crystal display device and / or an organic EL display device.

[0086] The dye of the present disclosure has excellent not only moist heat resistance but also radical resistance, and therefore can be used in applications other than optical filters. Examples include applications for writing instruments, particularly ballpoint pen inks, stamp inks, printing inks, inkjet inks, clothing dyeing, cell dyeing, blood detection, fluorescent dyes, indicators such as pressure-sensitive, heat-sensitive, and temperature-sensitive materials, optical recording materials, cosmetics, eyeglass lenses, contact lenses, and hair dyes. In particular, eyeglass lenses and contact lenses are preferred.

[0087] <Eyeglass Lens> The eyeglass lens of the present disclosure contains the compound of the present disclosure described above. There are no particular limitations on the resin that can be used in the eyeglass lens of the present disclosure, as long as it satisfies the physical properties required for eyeglass lenses, such as transparency, refractive index, processability, and hardness after curing. The resin may be a thermoplastic resin or a thermosetting resin. Examples of thermoplastic resins that can be used in eyeglass lenses include polycarbonate (PC). Examples of thermosetting resins include urethane resins and episulfide resins. As the urethane resin, a thiourethane resin is preferred. As the resin, a thiourethane resin is preferred from the viewpoint of a high refractive index, and a polycarbonate resin is preferred from the viewpoint of good transparency. That is, the resin in the eyeglass lens of the present disclosure is preferably at least one selected from the group consisting of a thiourethane resin and a polycarbonate resin.

[0088] For details of the thiourethane resins and episulfide resins suitable as resins for eyeglass lenses of the present disclosure, reference can be made to the descriptions in JP-A-2009-256692, JP-A-2007-238952, JP-A-2009-74624, JP-A-2015-212395, and JP-A-2016-84381.

[0089] The spectacle lens of the present disclosure may contain only one type of resin, or may contain two or more types. The content of the resin in the spectacle lens of the present disclosure is not particularly limited, and is, for example, preferably 30% by mass to 99.99% by mass, more preferably 50% by mass to 99.99% by mass, and even more preferably 60% by mass to 99.99% by mass, relative to the total mass of the spectacle lens. When the content of the resin in the spectacle lens of the present disclosure is within the above range, a lightweight and thin lens can be produced.

[0090] The eyeglass lenses of the present disclosure may contain other components in addition to the resin, such as ultraviolet absorbers, plasticizers, anti-degradants (e.g., antioxidants, peroxide decomposers, radical inhibitors, metal deactivators, acid scavengers, and amines), dyes, internal mold release agents, deodorizers, etc.

[0091] The manufacturing method of the eyeglass lens of the present disclosure is not particularly limited as long as it can manufacture the eyeglass lens of the present disclosure described above. For example, when the resin contained in the eyeglass lens is a thermoplastic resin, the eyeglass lens of the present disclosure can be manufactured by kneading a resin composition containing the resin, the compound of the present disclosure described above, and, if necessary, other additives such as an ultraviolet absorber, using a melt extruder, molding the kneaded mixture into pellets, and applying a known molding method such as injection molding to the obtained resin composition pellets. For example, when the resin contained in the eyeglass lens is a thermosetting resin, the eyeglass lens of the present disclosure can be manufactured by preparing a resin composition containing a monomer that is a resin precursor, the compound of the present disclosure described above, a polymerization catalyst (e.g., dibutyltin dichloride), and, if necessary, other optional ultraviolet absorbers and other additives, filling the obtained resin composition into a mold (forming die), and curing it by heating.

[0092] <Contact Lenses> The contact lenses of the present disclosure contain the compound of the present disclosure described above. The compound of the present disclosure functions as a dye, and because the compound of the present disclosure has good heat resistance, it can be suitably used in contact lenses that are always used in a wet state. The contact lenses may be hard or soft contact lenses. The contact lenses of the present disclosure are not particularly limited in terms of their components other than containing the compound of the present disclosure described above, and can be used in combination with known components used in contact lenses. The dye, which is the compound of the present disclosure, has good radical resistance, and can therefore be used in combination with polymerizable compositions generally used in the production of contact lenses.

[0093] The content of the compound of the present disclosure in the contact lens of the present disclosure is not particularly limited and may be appropriately selected depending on the purpose. In particular, from the viewpoint of achieving good blue light blocking properties, the content of the dye, which is the compound of the present disclosure, is preferably 0.002% by mass to 0.10% by mass, more preferably 0.005% by mass to 0.08% by mass, and even more preferably 0.01% by mass to 0.08% by mass, based on the total solid content of the contact lens.

[0094] Examples of additional components contained in contact lenses include polymerizable compounds, and other components may be contained depending on the purpose. Contact lenses are worn directly on the surface of the eyeball, and therefore are always in contact with a liquid having a composition similar to physiological saline. Therefore, from the viewpoint of maintaining the effect even when the contact lens is in contact with water, particularly an aqueous solution having a composition similar to physiological saline, for a long period of time, a polymerizable compound having a carbonyl group and a hydroxy group in the molecule is preferred as the polymerizable compound used in contact lenses. Examples of polymerizable compounds having a carbonyl group include (meth)acrylates, alkyl (meth)acrylates, hydroxyalkyl (meth)acrylates, phenoxyalkyl (meth)acrylates, and alkylene glycol (meth)acrylic acids, and more specifically, examples thereof include methacrylic acid (MAA), hydroxyethyl methacrylate (HEMA), ethylene glycol dimethacrylate (ED), 2-hydroxy-3-phenoxypropyl acrylate (HPPA), phenoxyethyl acrylate (POEA), phenoxyethyl methacrylate (POEMA), benzyl acrylate (BA), and lauryl methacrylate (LMA). Among these, preferred polymerizable compounds include hydroxyethyl methacrylate (HEMA), ethylene glycol dimethacrylate (ED), and the like, which are polymerizable compounds having a carbonyl group and a hydroxy group in the molecule, and 2-hydroxyethyl methacrylate is more preferred.

[0095] The contact lens may contain only one type of polymerizable compound, or two or more types may be used in combination. The content of the polymerizable compound relative to the total solid content of the contact lens is preferably 90% by mass or more but less than 100% by mass, more preferably 95% by mass or more but less than 100% by mass, and even more preferably 97% by mass or more but less than 100% by mass.

[0096] [Other Components] In addition to the dye, which is the compound of the present disclosure, and the polymerizable compound described above, the contact lens of the present disclosure may contain other components depending on the purpose. Examples of other components include an ultraviolet absorber, a dye other than the compound of the present disclosure, a polymerization initiator, a sensitizer, a polymerization inhibitor, a crosslinking agent, a plasticizer, and an anti-degradant (e.g., an antioxidant, a peroxide decomposer, a radical inhibitor, a metal deactivator, an acid scavenger, an amine, etc.).

[0097] The novel compound of the present disclosure is useful as a dye, and since the dye of the present disclosure has excellent moist heat resistance, it is suitable for use in various applications including dyes. Examples of preferred applications are as described above in the composition of the present disclosure.

[0098] The present disclosure will be described in detail below using examples, but the present disclosure is not limited thereto. In these examples, "%" and "parts" mean "% by mass" and "parts by mass", respectively, unless otherwise specified. In addition, in polymer compounds, unless otherwise specified, the molecular weight is the weight average molecular weight (Mw), and the ratio of the constituent units is the molar percentage. The weight average molecular weight (Mw) is a value measured as a polystyrene equivalent value by gel permeation chromatography (GPC).

[0099] Example 1 Synthesis of Exemplary Compound S-6 According to the synthesis scheme below, 3-(1,3-di-tert-butyl-5-hydroxypyrazol-4-yl)-4-hydroxy-3-cyclobutene-1,2-dione (referred to as compound (A) in the synthesis scheme below) and 4-tert-butyl-2-(N,N-dipropylamino)thiazole, a compound represented by general formula (2) (referred to as compound (B) in the synthesis scheme below), were synthesized.

[0100]

[0101] A mixture of 1.03 g of the resulting 3-(1,3-di-tert-butyl-5-hydroxypyrazol-4-yl)-4-hydroxy-3-cyclobutene-1,2-dione [compound (A)], 1.02 g of 4-tert-butyl-2-(N,N-dipropylamino)thiazole [compound (B)], 5 mL of toluene, and 5 mL of 2-butanol was heated to reflux at 90°C for 3 hours. Water generated during heating to reflux was removed using a Dean-Stark apparatus. The reaction mixture was concentrated under reduced pressure and purified by silica gel chromatography to obtain 260 mg of the target compound S-6 of Example 1. The synthetic scheme is shown below.

[0102]

[0103] (Confirmation of Product S-6) The proton nuclear magnetic resonance ( １ H-NMR, solvent: chloroform (CDCl ３ )), the chemical shifts δ were 0.96 (t, 6H), 1.41 (s, 9H), 1.51 (s, 9H), 1.56 (s, 9H), 1.74 (m, 4H), and 3.58 (br., 4H), confirming the structure of Compound S-6. The maximum absorption wavelength (λmax) of Compound S-6 measured by the previously described method was 585 nm (ε: 2.66 × 10 ５ (solvent: chloroform)), absorbance: 0.64.

[0104] Example 2: Synthesis of exemplified compound S-8 Example 1: Synthesis of compound A-1 A mixture of 622 mg of 3-(1-tert-butyl-5-hydroxy-3-methylpyrazol-4-yl)-4-hydroxy-3-cyclobutene-1,2-dione (compound (C)), 730 mg of 4-tert-butyl-2-(N,N-dipropylamino)thiazole (compound (B)), 4 mL of toluene, and 4 mL of 2-butanol was heated to reflux at 90°C for 3 hours. Water generated during heating to reflux was removed using a Dean-Stark apparatus. The reaction mixture was concentrated under reduced pressure and purified by silica gel chromatography to obtain 650 mg of the target compound S-8 of Example 2. The synthesis scheme is shown below.

[0105]

[0106] (Confirmation of Product S-8) The proton nuclear magnetic resonance ( １ H-NMR, solvent: DMSO-d ６ ), the chemical shifts δ were 0.98 (t, 6H), 1.53 (s, 9H), 1.58 (s, 9H), 1.75 (m, 4H), 2.48 (s, 3H), 3.40 (br., 2H), 3.73 (br., 2H), and 15.19 (br., 1H), confirming the structure of Compound S-8. The maximum absorption wavelength (λmax) of Compound S-8 measured by the previously described method was 579 nm (ε: 1.79 × 10 ５ (solvent: chloroform), absorbance: 0.64

[0107] Examples 3 to 5 Exemplary Compounds S-2, S-3, and S-16 were synthesized in the same manner as in Example 1, except that the starting material, Compound (A), was changed as follows. The maximum absorption wavelengths and absorbances measured in the same manner as in Example 1 are as shown below.

[0108] Example 3: S-2 Maximum absorption wavelength (λmax) 565 nm, (ε: 1.82×10 ５ (Solvent: chloroform)), absorbance: 0.65 Example 4: S-3 Maximum absorption wavelength (λmax) 575 nm (ε: 1.78 × 10 ５ (Solvent: chloroform), absorbance: 0.64 Example 5: S-16 Maximum absorption wavelength (λmax) 580 nm (ε: 1.95 × 10 ５ (solvent: chloroform), absorbance: 0.68

[0109] Example 6 (Preparation of Composition) Using the exemplary compound S-6, which is the dye of Example 1 obtained above, a composition containing a resin (first embodiment of the composition) was prepared according to the following formulation. 20 mg of the exemplary compound S-6, which is the dye of Example 1 obtained, and 500 mg of polymethyl methacrylate were dissolved in 5 ml of chloroform, and a thin film was formed on a glass substrate (5 cm x 5 cm, Eagle XG, manufactured by AXEL) by spin coating [500 rpm (revolutions per minute), 30 seconds]. The thin film was then dried on a hot plate heated to 80°C for 1 minute. First, the maximum absorption wavelength and absorbance were measured using the initial thin film using the method described above. The results are shown in the "Initial State" column of Table 1 below.

[0110] (Evaluation of moist heat resistance) The moist heat resistance test was carried out using a thermo-hygrostat (IG420 manufactured by Yamato Scientific Co., Ltd.) at a temperature of 60°C and a humidity of 90% RH. The maximum absorption wavelength and absorbance of the thin film were measured after aging for 160 hours. The rate of decrease in absorbance before and after the moist heat resistance test was calculated. The lower the rate of decrease, the better the composition's moist heat resistance was evaluated. The results are shown in the "After aging under moist heat" column in Table 1.

[0111] (Absorbance Decrease Rate After Humid Heat Aging) The absorbance decrease rate after humid heat aging was calculated according to the following formula. The results are shown in Table 1 below. Absorbance decrease rate after humid heat aging (%) = [(absorbance in initial state) - (absorbance after humid heat aging)] / (absorbance in initial state) x 100

[0112] Examples 7 to 10, Comparative Examples 1 and 2 Compositions were prepared using the dyes of Examples 2 to 5 and the following comparative compounds H-1 and H-2 as dyes in the same manner as in Example 6, and their moist heat resistance was evaluated. The results are shown in Table 1 below.

[0113]

[0114]

[0115] As is clear from Table 1, when compositions containing the exemplary compounds (dyes) obtained in Examples 1 to 5, i.e., the compositions of Examples 6 to 10, were prepared and evaluated, it was found that the moist heat resistance was significantly improved compared to the compositions containing the comparative compounds of Comparative Examples 1 and 2. In particular, it was found that when compounds having many bulky substituents such as t-Bu, such as Compounds S-3 and S-6, were used, the moist heat resistance of the compositions was further improved.

[0116] Example 11 (Preparation of Composition) Using the dye S-6 of Example 1 obtained above, a composition of the present disclosure (second embodiment of the composition) containing a monomer and a polymerization initiator was prepared according to the following formulation: 0.02 parts of compound S-6, the dye of Example 1, and 0.3 parts of phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (Fujifilm Wako Pure Chemical Industries, Ltd.: photopolymerization initiator) were added to 30 parts of 2-hydroxyethyl methacrylate (monomer), and the mixture was stirred with a magnetic stirrer for 30 minutes. The resulting mixture was filtered through a 0.45 μm filter (manufactured by Advantec Co., Ltd., PTFE) to prepare a polymerizable composition (second embodiment of the composition).

[0117] (Evaluation of Radical Resistance) A 100 μm thick silicone film with a 1 cm × 1 cm central cutout was placed on a glass substrate (2.5 cm × 2.5 cm, Eagle XG, manufactured by AXEL), and two drops (0.4 mL) of the polymerizable composition of Example 11 were dropped into the center of the film using a dropper. Another glass substrate (2.5 cm × 2.5 cm, Eagle XG, manufactured by AXEL) was then placed on top of the film to obtain a laminate having the polymerizable composition in the glass substrate. The transmission spectrum was measured using a spectrophotometer (Shimadzu Corporation, UV3600) to measure the absorbance in the initial state. The results are shown in the "Initial State" column in Table 2 below. After the formation of the laminate, the obtained laminate was irradiated with a UV lamp (manufactured by HOYA-SCHOTT, EXECURE 3000-W, 100 mW / cm ２, 30 seconds). Thereafter, the transmission spectrum after exposure was measured again, and the absorbance of the laminate after exposure was measured. The results are shown in the "After exposure" column in Table 2 below. (Absorbance reduction rate after exposure) The absorbance reduction rate after exposure was calculated according to the following formula. The results are shown in Table 2 below. Absorbance reduction rate after exposure (%) = [(absorbance in initial state) - (absorbance after exposure)] / (absorbance in initial state) x 100

[0118] Examples 12 to 15, Comparative Examples 3 and 4 Polymerizable compositions were prepared using the dyes of Examples 2 to 5, the comparative compound H-1, and the comparative compound H-2 in the same manner as in Example 11, and the maximum absorption wavelength, absorbance, and radical resistance were evaluated. The results are shown in Table 2 below.

[0119]

[0120] As is clear from Table 2, the compositions containing the exemplary compounds (dyes) of Examples 1 to 5 exhibited suppressed absorbance reduction after exposure, and the dyes of Examples 1 to 5 exhibited excellent radical resistance. In particular, compositions using compounds having many bulky substituents such as t-Bu, such as Compound S-3 and Compound S-6, were found to have improved radical resistance as well as moist heat resistance. On the other hand, the evaluation results of Comparative Examples 3 and 4 confirmed that the comparative compounds, which are known squarylium dyes, all exhibited extremely low radical resistance and were unsuitable for use in polymerizable compositions.

[0121] From the above evaluation results, the dyes of the examples have good resistance to moist heat and radicals, and can be suitably used in both resin-containing compositions and polymerizable compositions, and have a wide range of applications.

[0122] The disclosure of Japanese Patent Application No. 2023-111717, filed on July 6, 2023, is incorporated herein by reference. All documents, patent applications, and technical standards mentioned in this disclosure are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A compound represented by the following general formula (1): In general formula (1), R １ , R ２ , and R ５ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ and R ４ each independently represents an alkyl group, an aryl group, or a heterocyclic group.

2. R in the general formula (1) ３ The compound of claim 1, wherein is an alkyl group.

3. R ​​in the general formula (1) ３ The compound according to claim 2, wherein is a tertiary alkyl group.

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

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

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

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

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

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

10. A method for producing a compound represented by the following general formula (1) using a compound represented by the following general formula (2). In general formula (2), R １ , and R ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ represents an alkyl group, an aryl group, or a heterocyclic group. In general formula (1), R １ , R ２ , and R ５ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R １ , and R ２ may be linked to form a ring with or without a linking group. ３ and R ４ each independently represents an alkyl group, an aryl group, or a heterocyclic group.