JP7122711B2 - Dye compound, optical filter and dye composition for spectacle lenses - Google Patents

Description

TECHNICAL FIELD The present invention relates to a compound that can be used as a dye, and a dye composition for an optical filter and a spectacle lens containing the compound.

2. Description of the Related Art Optical filters are used to cut light of specific wavelengths from light emitted from lighting devices, display devices, etc., and from natural light.
For example, Patent Document 1 describes protective sheets and spectacle lenses containing a dye having an absorption maximum between 450 and 500 nm.

WO2017/169370

Optical filters, in particular spectacle lenses, are required to provide good color contrast of objects (articles, images, landscapes, etc.) when used. In order to improve the contrast of specific colors, it is necessary to selectively cut light of specific wavelengths. For example, in order to improve the contrast between blue and green, it is effective to effectively cut off light with short wavelengths around 500 nm. For this purpose, a compound that has a maximum absorption wavelength of 490 to 500 nm, a narrow half width, and can be applied to optical filters such as eyeglasses is desired.
Japanese Patent Laid-Open No. 2004-100000 does not consider improving the contrast between blue and green, which is an object to be visually observed, or the half-value width of the dye for spectacle lenses or the like.

An object of the present invention is to provide a compound having a maximum absorption wavelength of 490 to 500 nm and a narrow half width.

The present inventors have made intensive studies to solve the above problems, and found that the compound represented by the following general formula (1) has a maximum absorption wavelength of 490 to 500 nm and a narrow half width. . Based on this knowledge, the inventors have further studied and completed the present invention.

That is, the compound of the present invention is a compound represented by the following general formula (1).

(In the general formula (1), R ¹ represents an optionally substituted fluorinated alkyl group, R ² represents an optionally substituted linear, branched or cyclic alkyl R ³ and R ⁴ are the same or different and represent an optionally substituted linear, branched or cyclic alkyl group or an optionally substituted aryl group. )

In the present invention, R ¹ in general formula (1) above is preferably a trifluoromethyl group.

In the present invention, at least one of R ³ and R ⁴ in the general formula (1) is preferably a linear alkyl group having 1 to 10 carbon atoms.
More preferably, R ³ and R ⁴ in general formula (1) are the same or different and represent a linear alkyl group having 1 to 3 carbon atoms.

R ² in the general formula (1) is preferably an optionally substituted linear, branched or cyclic alkyl group having 1 to 10 carbon atoms.

R ² , R ³ and R ⁴ in the general formula (1) are preferably ethyl groups.

The optical filter of the present invention is characterized by containing the compound of the present invention.
In the present invention, the optical filter may be a spectacle lens.
The dye composition for spectacle lenses of the present invention is characterized by containing the compound of the present invention.

According to the present invention, it is possible to provide a compound having a maximum absorption wavelength of 490 to 500 nm and a narrow half width. The compound of the present invention can be suitably used as a pigment or the like for optical filters such as spectacle lenses.

The compound of the present invention is a compound represented by the following general formula (1).

(In the general formula (1), R ¹ represents an optionally substituted fluorinated alkyl group, R ² represents an optionally substituted linear, branched or cyclic alkyl R ³ and R ⁴ are the same or different and represent an optionally substituted linear, branched or cyclic alkyl group or an optionally substituted aryl group. )

R ¹ in general formula (1) represents an optionally substituted fluorinated alkyl group. The optionally substituted fluorinated alkyl group preferably has 1 to 6 total carbon atoms, more preferably 1 to 3 carbon atoms, and still more preferably 1 to 2 carbon atoms. Preferred examples of optionally substituted fluorinated alkyl groups include alkyl groups having 1 to 6 carbon atoms in which some or all of the hydrogen atoms are substituted with fluorine atoms. The fluorinated alkyl group which may have a substituent may be linear, branched or cyclic, but a linear fluorinated alkyl group is preferred. Examples of optionally substituted fluorinated alkyl groups include trifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl. group, 3,3,3-trifluoropropyl group, and the like. R ¹ is preferably a trifluoromethyl group or a pentafluoroethyl group, more preferably a trifluoromethyl group.

R ² in the general formula (1) represents an optionally substituted linear, branched or cyclic alkyl group. A linear, branched or cyclic alkyl group which may have a substituent preferably has a total carbon number of 1 to 20, more preferably 1 to 15, and 1 to 12. is more preferred, and 1 to 10 is particularly preferred. Further, the linear, branched or cyclic alkyl group which may have a substituent is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms which may have a substituent. is preferred.
Linear, branched or cyclic alkyl groups which may have a substituent include, for example, methyl group, ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-heptyl group, n -octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, 2-(4-cyclohexylphenoxy)ethyl group, Linear alkyl group optionally having a substituent such as 3-phthalimidopropyl group; i-propyl group, i-butyl group, t-butyl group, 2-methylbutyl group, 1-methylbutyl group, neo-pentyl group , 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2 ,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1 , 1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group , 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, t-octyl group, 3,5,5-trimethylhexyl group, 4-ethyl Octyl group, 4-ethyl-4,5-dimethylhexyl group, 1,3,5,7-tetramethyloctyl group, 2-butyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, 6- methyl-4-butyloctyl group, 3,5-dimethylheptadecyl group, 2,6-dimethylheptadecyl group, 2,4-dimethylheptadecyl group, 2,2,5,5-tetramethylhexyl group, 1- Branched chain alkyl groups optionally having substituents such as cyclopentyl-2,2-dimethylpropyl group and 1-cyclohexyl-2,2-dimethylpropyl group; cyclopentyl group, cyclohexyl group, 4-t-butylcyclohexyl group , 2,6-di-t-butyl-4-methylcyclohexyl, and optionally substituted cyclic alkyl groups. Among them, R ² is more preferably an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a 2-(4-cyclohexylphenoxy)ethyl group, A 3-phthalimidopropyl group and a 2-ethylhexyl group are more preferred, and an ethyl group is particularly preferred.

In the above general formula (1), R ³ and R ⁴ are the same or different and may be a linear, branched or cyclic alkyl group optionally having a substituent or an aryl optionally having a substituent represents a group.
The linear, branched or cyclic alkyl group optionally having substituent(s) for R ³ and R ⁴ is the linear, branched or cyclic alkyl group optionally having substituent(s) described for R ² above. A cyclic alkyl group and the like can be mentioned. The optionally substituted linear, branched or cyclic alkyl group for R ³ and R ⁴ is preferably a linear alkyl group having 1 to 10 carbon atoms, and a linear alkyl group having 1 to 8 carbon atoms. is more preferred, and in one aspect, an ethyl group or an n-octyl group is even more preferred.

Aryl groups for R ³ and R ⁴ include monocyclic or polycyclic aromatic ring groups having 6 to 20 carbon atoms. Specific examples of monocyclic or polycyclic aromatic ring groups having 6 to 20 carbon atoms include monocyclic aromatic hydrocarbon groups such as phenyl; naphthyl, anthracenyl, naphthacenyl, pentacenyl, phenanthrenyl; Examples include polycyclic aromatic hydrocarbon groups such as pyrenyl groups.
The aryl group which may have a substituent preferably has a total carbon number of 6 to 20, more preferably 6 to 15, even more preferably 6 to 12, and 6 to 10. It is particularly preferred to have
Specific examples of the aryl group optionally having substituents include, for example, a phenyl group optionally substituted with an alkyl group (e.g., phenyl group, 3-methylphenyl group, 2,4-dimethylphenyl group), A naphthyl group optionally substituted with an alkyl group, such as 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group and the like. Among these, a phenyl group, a 3-methylphenyl group and a 2,4-dimethylphenyl group are preferred.

In one aspect of the present invention, from the viewpoint of the half-value width, at least one of R ³ and R ⁴ in the general formula (1) is preferably a linear alkyl group having 1 to 10 carbon atoms. 8 is more preferably a straight chain alkyl group. In addition, since the half-value width becomes narrower, R ³ and R ⁴ in the general formula (1) are the same or different, more preferably a linear alkyl group having 1 to 3 carbon atoms, and more preferably an ethyl group. is particularly preferred.

Examples of preferred embodiments of the compounds of the present invention include compounds 1 to 5 in Examples below. These compounds have an absorption maximum between 490 and 500 nm and a half-width of less than 50 nm. These compounds also have good heat resistance. Among them, the compound 1, 2 or 5 is more preferable, the compound 1 or 5 is more preferable, and the gram extinction coefficient is high, so the compound 1 is particularly preferable from the viewpoint of narrow half width. Compound 1 is a compound in which R ¹ in the general formula (1) is a trifluoromethyl group, and R ² , R ³ and R ⁴ are ethyl groups. Compound 5 is a compound represented by general formula (1) above, wherein R ¹ is a trifluoromethyl group, R ² is a 2-ethylhexyl group, and R ³ and R ⁴ are ethyl groups.
In one aspect of the present invention, R ² , R ³ and R ⁴ in general formula (1) are particularly preferably ethyl groups. A compound in which R ² , R ³ and R ⁴ in the general formula (1) are ethyl groups also has the effect of reducing fluorescence. When the fluorescence is low, the color contrast of an object viewed through an optical filter containing the compound can be improved.

The method for producing the compound of the present invention will be described below by giving an example of the synthesis method, but the method for producing the compound of the present invention is not limited to the following method. Moreover, when carrying out the reactions described below, functional groups other than the relevant site may be protected in advance with an appropriate protecting group as necessary, and may be deprotected at an appropriate stage.

The compound of the present invention can be produced, for example, by reacting a compound represented by general formula (2) shown below with a compound represented by general formula (3).

In general formula (2) above, R ² , R ³ and R ⁴ have the same meanings as R ² , R ³ and R ⁴ in general formula (1). In general formula (3) above, R ¹ has the same definition as R ¹ in general formula (1).

The method for producing the compound represented by formula (2) is not particularly limited. For example, it can be produced by the methods described in JP-A-11-501926, JP-A-2017-206640, US2003/0165714, and the like.

The method for producing the compound represented by formula (3) is not particularly limited. For example, it can be produced by the method described in JP-A-62-084064.

Conditions for reacting the compound represented by the general formula (2) and the compound represented by the general formula (3) are not particularly limited. The reaction is usually carried out in a solvent in the presence of an acid or base.
The solvent is not particularly limited as long as it is inert to the reaction. Examples include methanol, ethanol, propanol, butanol, pentanol, hexanol, acetic acid, acetic anhydride, toluene, xylene, dimethylformamide, N-methylmorpholine, dimethylsulfoxide, dimethylacetamide, pyridine and the like.
The temperature during the reaction can be 40 to 100°C, preferably 40 to 80°C. The reaction time can be 0.5 to 24 hours, preferably 0.5 to 12 hours.

Isolation and purification of the product in the above production method can be carried out by appropriately combining methods used in ordinary organic synthesis, such as filtration, extraction, washing, drying, concentration, crystallization, various types of chromatography, and the like.

The compound of the present invention is a styryl dye and has an isoxazolone skeleton.
The compound of the present invention usually has a maximum absorption wavelength of 490-500 nm. Therefore, blue-green light can be effectively absorbed. When such a compound is used in an optical filter such as a spectacle lens, for example, when an object (article, image, etc.) is viewed through the optical filter, the contrast between blue and green of the object can be improved. can. The maximum absorption wavelength of the compound of the present invention can be determined, for example, as the wavelength of the maximum absorption peak obtained by measuring the absorption spectrum of a chloroform solution of the above compound with an ultraviolet-visible spectrophotometer.
The compound of the present invention preferably has a maximum absorption wavelength of 492-496 nm.

The compound of the present invention preferably has a half-value width of less than 50 nm. When the half width is as narrow as less than 50 nm, it is possible to selectively absorb light having a wavelength near the maximum absorption wavelength. Therefore, when the compound of the present invention is used for an optical filter such as a spectacle lens, the contrast between blue and green of the object viewed through the optical filter can be further improved. In one aspect, the compound of the present invention preferably has a half-value width of 45 nm or less, more preferably 40 nm or less, from the viewpoint of being able to further improve the contrast between blue and green as a visual target when used in an optical filter. more preferably, and particularly preferably 35 nm or less.
In the present specification, the half-value width means the full width at half maximum (FWHM) of the peak, and is the difference in wavelength between two points having half the maximum absorbance at the absorption maximum peak of the compound. is. The half width can be determined from the maximum absorption peak obtained by measuring the absorption spectrum of a chloroform solution of the compound with an ultraviolet-visible spectrophotometer, for example. The maximum absorption wavelength and half-value width of a compound can be determined by the method described in Examples.

The compound of the present invention is preferably a compound that dissolves in an organic solvent.
Examples of organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.), ketones (methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, 3-heptanone, etc.), ethers (e.g., propylene glycol monomethyl ether acetate , methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, etc.), esters (e.g., methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl lactate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate etc.) and mixed solvents of two or more thereof.
The compound of the present invention preferably dissolves in at least one of the above organic solvents by 0.1% by mass or more, for example, preferably 0.1% by mass or more and 50% by mass or less, and 1% by mass or more. It is more preferable to dissolve 40% by mass or less, and more preferably 2% to 30% by mass. More preferably, the solubility in organic solvents at 20°C is within this range. When the solubility in an organic solvent is within this range, the compound of the present invention is preferable because of good manufacturability when it is used for manufacturing optical filters such as spectacle lenses.

The compound of the present invention preferably has a thermal decomposition temperature of 200°C or higher, more preferably 210°C or higher, for example, 215 to 400°C. The pyrolysis temperature can be measured with a thermogravimetry device.

Since the compound of the present invention has a narrow half-width, it can selectively absorb light near the absorption maximum wavelength (490 to 500 nm). Therefore, the compound of the present invention is preferably used, for example, as a dye for optical filters. When the compound of the present invention is used in an optical filter, the contrast between blue and green in a visually observed object can be improved when the object is visually observed through the optical filter.

The compound of the present invention can be made into a dye composition by mixing with, for example, a resin. A dye composition is suitably used as a coloring composition.
The resin is not particularly limited, and a thermoplastic resin, a photocurable resin, a thermosetting resin, or the like may be appropriately selected according to the intended use of the coloring composition. For example, acrylic resin, polycarbonate resin, polystyrene resin, low-density polyethylene resin, polypropylene resin, polyurethane resin, polythiourethane resin, polyamide resin, polyacetal resin, polyphenylene sulfide resin, polyethylene terephthalate resin, polybutylene terephthalate resin, polycycloolefin resin , polysulfone resin, polyethersulfone resin, fluorine resin, silicone resin, polyester resin, epoxy resin, phenol resin, melamine resin, and the like. These may be used alone or in combination of two or more.

The compounding amount of the compound of the present invention in the dye composition is, for example, preferably 0.001 to 50% by mass of the compound with respect to the total solid content of the dye composition, and is 0.01 to 40% by mass. is more preferable.

The dye composition may contain optional components other than the compound and resin of the present invention, depending on its use. Optional components include, for example, antioxidants, antifoaming agents, other dyes (dyes, pigments, etc.), ultraviolet absorbers, infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers, and the like.
The method for producing the dye composition is not particularly limited, and for example, the compound and resin of the present invention, and optional ingredients blended as desired may be mixed.

The compound of the present invention and the dye composition containing the same are suitably used for producing optical filters and the like. An optical filter or the like containing the compound of the present invention is also included in the present invention. The optical filter is not particularly limited as long as it contains the compound of the present invention.
The optical filter is not particularly limited, and examples thereof include lenses such as spectacle lenses, color filters, and color conversion filters. Spectacles also include sunglasses and sports goggles. These optical filters can be suitably used for spectacles (including sunglasses and goggles), imaging devices, lighting tools, display devices, and the like. Among others, the compound of the present invention is effective in improving the contrast between blue and green of an object to be visually observed, and therefore is preferably used for a spectacle lens.
A dye compound containing the compound of the present invention is particularly suitable as a dye composition for spectacle lenses. A spectacle lens comprising a compound of the invention is an example of a preferred embodiment of the invention.

The optical filter may contain the compound of the present invention, and may have, for example, a support and, if necessary, an optical functional layer, etc., in the same manner as conventional filters. In the optical filter, the compound of the invention is preferably contained in the support or the optical functional layer.

The configurations of the support and the optical function layer are not particularly limited either. For example, the support is usually formed using a transparent resin. Examples of transparent resins include cyclic olefin-based resins, aromatic polyether-based resins, polyimide-based resins, fluorene polycarbonate-based resins, fluorene polyester-based resins, polycarbonate-based resins, polyamide (aramid)-based resins, polyarylate-based resins, and polysulfones. resin, polyethersulfone resin, polyparaphenylene resin, polyamideimide resin, polyethylene naphthalate (PEN) resin, fluorinated aromatic polymer resin, (modified) acrylic resin, epoxy resin, polyurethane resins, polythiourethane resins, episulfide resins, polyolefin resins, and the like.

A manufacturing method of the optical filter is not particularly limited. For example, as a method for forming an optical functional layer containing the compound of the present invention on a support, the compound of the present invention, a binder resin, etc. are dissolved or dispersed in a solvent, followed by a dip coating method, an air knife coating method and a curtain coating method. A coating method such as a coating method, a roller coating method, a wire bar coating method, a gravure coating method, a spin coating method and an extrusion coating method may be used to form a coating film on a support. Examples of the solvent include, but are not particularly limited to, the above-described organic solvents.

Further, as a method for producing an optical functional layer or support containing the compound of the present invention, the compound of the present invention, a photocurable resin and/or a thermosetting resin, and a photopolymerization initiator and/or a thermal polymerization initiator are prepared. After mixing, a cured film is formed by light irradiation and/or heat treatment, and this can be used as an optical function layer or support.

Examples of a method for producing a lens, which is an example of an optical filter, include a method of kneading a transparent resin with the compound of the present invention and molding by an injection molding method, a compression molding method, an extrusion molding method, or the like; Various methods such as a method of forming an optical functional layer containing the compound of the present invention can be employed.

EXAMPLES The present invention will be described below in more detail with examples, but the present invention is not limited to these examples.

The instruments used for measuring the physical properties of the obtained compounds are as follows.
(LC/MS)
Shimadzu Corp. High performance liquid chromatograph mass spectrometer LCMS-2010EV (ESI method)
(NMR)
Nuclear magnetic resonance apparatus JNM-ECZ400S manufactured by JEOL Ltd.

<Example 1>
Compound 1 was obtained by the following method.
Synthesis of 3-trifluoromethyl-5-hydroxyisoxazole sodium salt 3-Trifluoromethyl-5-hydroxyisoxazole sodium salt was obtained by the method described in JP-A-62-084064.

Synthesis of 2-ethoxy-4-(diethylamino)benzaldehyde 2-ethoxy-4-(diethylamino)benzaldehyde was obtained by the method described in JP-A-11-501926.

Synthesis of Compound 1 1.0 g of 3-trifluoromethyl-5-hydroxyisoxazole sodium salt was placed in a 25 mL three-necked flask equipped with a condenser and a thermometer, and 0.5 mL of concentrated hydrochloric acid was added under an ice bath. .5 mL was added. 1.32 g of 2-ethoxy-4-(diethylamino)benzaldehyde was added, and the mixture was heated and stirred at 70° C. for 3 hours. After allowing to cool, the mixture was discharged into water, extracted with toluene, and the solvent was distilled off to obtain a crude product. The resulting crude product was washed with methanol to obtain compound 1 (yield 17%).
LC-MS: m/z=357 [M+H] ⁺
δ1.29 (t, 6H), δ1.49 (t, 3H), δ3.53 (q, 4H), δ4.11 (q, 2H), δ5.96 (1H, d, J=0.8Hz) , δ6.40 (1H, dd, J = 3.6, 0.8Hz), δ8.16 (1H, s), δ9.28 (1H, d, J = 3.6Hz)

<Example 2>
Compound 2 was obtained by the following method.
Synthesis of 2-(4-cyclohexylphenoxy)ethanol 2-(4-Cyclohexylphenoxy)ethanol was obtained by the method described in US2130525.

Synthesis of 2-(4-cyclohexylphenoxy)ethyl tosylate Using 2-(4-cyclohexylphenoxy)ethanol, 2-(4-cyclohexylphenoxy ) to give the ethyl tosylate.

Synthesis of 2-[2-(4-cyclohexylphenoxy)ethoxy]-4-(diethylamino)benzaldehyde Using 2-(4-cyclohexylphenoxy)ethyl tosylate, the same method as described in JP-A-2017-206640 gave 2-[2-(4-cyclohexylphenoxy)ethoxy]-4-(diethylamino)benzaldehyde.

Synthesis of compound 2 Except for changing 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of compound 1 to 2-[2-(4-cyclohexylphenoxy)ethoxy]-4-(diethylamino)benzaldehyde, Compound 2 was obtained in analogy to the synthesis.
LC-MS: m/z=531 [M+H] ⁺

<Example 3>
Compound 3 was obtained by the following method.
Synthesis of 1-{N-(3-ethoxy-4-formylphenyl)-N-(2,4-dimethylphenyl)amino}-n-octane By the method described in JP-A-2017-206640, 1-{ N-(3-ethoxy-4-formylphenyl)-N-(2,4-dimethylphenyl)amino}-n-octane was obtained.

Synthesis of Compound 3 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of Compound 1 was replaced with 1-{N-(3-ethoxy-4-formylphenyl)-N-(2,4-dimethylphenyl)amino}- Compound 3 was obtained in the same manner as in the synthesis of compound 1, except that n-octane was used.
LC-MS: m/z=517 [M+H] ⁺

<Example 4>
Compound 4 was obtained by the following method.
Synthesis of 1-{N-(2,4-dimethylphenyl)-N-[4-formyl-3-(3-phthalimidopropyloxy)phenyl]amino}-n-octane described in JP-A-2017-206640 A procedure similar to the method gave 1-{N-(2,4-dimethylphenyl)-N-[4-formyl-3-(3-phthalimidopropyloxy)phenyl]amino}-n-octane.

Synthesis of compound 4 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of compound 1 was replaced with 1-{N-(2,4-dimethylphenyl)-N-[4-formyl-3-(3-phthalimidopropyloxy ) Compound 4 was obtained in the same manner as in the synthesis of Compound 1, except that phenyl]amino}-n-octane was used.
LC-MS: m/z=676 [M+H] ⁺

<Example 5>
Compound 5 was obtained by the following method.
Synthesis of 4-diethylamino-2-(2-ethylhexyloxy)benzaldehyde 4-diethylamino-2-(2-ethylhexyloxy)benzaldehyde was obtained by the method described in US2003/0165714.

Synthesis of compound 5 In the same manner as in the synthesis of compound 1, except that 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of compound 1 was changed to 4-diethylamino-2-(2-ethylhexyloxy)benzaldehyde, compound Got 5.
LC-MS: m/z=441 [M+H] ⁺

Compounds 1 to 5 are compounds in which R ¹ , R ² , R ³ and R ⁴ are substituents shown in Table 1 in the following general formula (1). In the substituents shown in Table 1, * represents a bonding site with general formula (1). _CF3 denotes a trifluoromethyl group and Et denotes an ethyl group. C ₈ H ₁₇ represents an n-octyl group.

<Comparative Example 1>
Synthesis of 3-tert-butylisoxazol-5(4H)-one 3-tert-butylisoxazol-5(4H)-one was obtained by the method described in JP-A-53-023968.

Synthesis of Comparative Compound 1 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of compound 1 was changed to 1-ethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde (Sigma-Aldrich), 3 Comparative compound 1 was obtained in the same manner as in the synthesis of compound 1, except that -trifluoromethyl-5-hydroxyisoxazole sodium salt was changed to 3-tert-butylisoxazol-5(4H)-one.
LC-MS: m/z=325 [M+H] ⁺

<Comparative Example 2>
Synthesis of Comparative Compound 2 Except for changing 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of compound 1 to 1-ethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde (Sigma-Aldrich) Comparative compound 2 was obtained in the same manner as the synthesis of compound 1.
LC-MS: m/z=313 [M+H] ⁺

Comparative compound 1 is a compound in which ^RA is a t-butyl group in the following general formula (4). Comparative compound 2 is a compound in which ^RA is a trifluoromethyl group in the following general formula (4).

<Comparative Example 3>
Synthesis of Comparative Compound 3 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of compound 1 was changed to 4-(diethylamino)-2-methylbenzaldehyde (Nacalai Tesque Co., Ltd.), and 3-trifluoromethyl-5 Comparative compound 3 was obtained in the same manner as in the synthesis of compound 1, except that -hydroxyisoxazole sodium salt was changed to 3-tert-butylisoxazol-5(4H)-one.
LC-MS: m/z=315 [M+H] ⁺

<Comparative Example 4>
Synthesis of Comparative Compound 4 Synthesis of Compound 1 and Synthesis of Compound 1 except that 2-ethoxy-4-(diethylamino)benzaldehyde in the synthesis of Compound 1 was changed to 4-(diethylamino)-2-methylbenzaldehyde (Nacalai Tesque Co., Ltd.). Comparative compound 4 was obtained in the same manner.
LC-MS: m/z=327 [M+H] ⁺

<Comparative Example 5>
Synthesis of Comparative Compound 5 The synthesis of compound 1 and the Comparative compound 5 was obtained in the same manner.
LC-MS: m/z=345 [M+H] ⁺

Comparative compounds 3 to 5 are compounds in which R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are substituents shown in Table 2 in the following general formula (5). In Table 2, tBu represents a t-butyl group, Me represents a methyl group, Et represents an ethyl group, CF ₃ represents a trifluoromethyl group, and EtO represents an ethoxy group.

The compounds obtained above were evaluated as follows. Table 3 shows the results.
<Spectral characteristic test>
For each compound obtained in Examples and Comparative Examples, the absorption spectrum in chloroform was measured, and the absorption maximum wavelength (λmax) and the half width of the absorption maximum peak at a wavelength of 400 to 800 nm were determined.
Each value of absorption spectrum, maximum absorption wavelength and half width was measured using a UV-visible spectrophotometer V-560 manufactured by JASCO Corporation.
(Evaluation criteria for half-value width)
A: FWHM is 35 nm or less B: FWHM is more than 35 nm and 40 nm or less C: FWHM is more than 40 nm and 45 nm or less D: FWHM is more than 45 nm and 50 nm or less E: FWHM is more than 50 nm and 55 nm Less than

<Heat resistance>
For some of the compounds obtained in Examples and Comparative Examples, the weight loss due to thermal decomposition was measured using a thermogravimetric analyzer TGA-50 manufactured by Shimadzu Corporation under the following measurement conditions. The temperature at the intersection of the tangent line at the inflection point seen in the part and the extension of the base line was measured as the decomposition initiation temperature.
(Measurement condition)
Measurement was performed under the conditions of a sample amount of 10 mg, a temperature increase rate of 10° C./min (maximum attained temperature of 400° C.), a nitrogen atmosphere, and a flow rate of 20 mL/min.
The heat resistance was evaluated from the decomposition initiation temperature according to the following criteria.
A: 210°C or higher B: 200°C or higher and lower than 210°C C: 190°C or higher and lower than 200°C

From the above results, Compounds 1 to 5 produced in Examples had maximum absorption wavelengths in the range of 490 to 500 nm and half widths of less than 50 nm. These compounds have a narrow half-value width, can selectively absorb light of 490 to 500 nm, and are useful for improving the contrast between blue and green. Compounds 1 to 3 and 5 also had good heat resistance. Comparative compounds 1, 3 and 5 had a half width of 50 nm or more. Comparative compound 2 had lower heat resistance than the compounds of the examples. The compound of Comparative Compound 4 had a maximum absorption wavelength on the longer wavelength side than 500 nm.

Claims (9)

A compound represented by the following general formula (1).

(In general formula (1), R ¹ represents an optionally substituted fluorinated alkyl group,
R ² represents an optionally substituted linear, branched or cyclic alkyl group,
R ³ and R ⁴ are the same or different and represent an optionally substituted linear, branched or cyclic alkyl group or an optionally substituted aryl group. ) 2. The compound according to claim 1, wherein R1 in the general formula ( ¹ ) is a trifluoromethyl group. 3. The compound according to claim 1, wherein at least one of R ³ and R ⁴ in the general formula (1) is a linear alkyl group having 1 to 10 carbon atoms. 4. The compound according to any one of claims 1 to 3, wherein R ³ and R ⁴ in the general formula (1) are the same or different and represent a linear alkyl group having 1 to 3 carbon atoms. The compound according to any one of claims 1 to 4, wherein R ² in the general formula (1) is an optionally substituted linear, branched or cyclic alkyl group having 1 to 10 carbon atoms. . 6. The compound according to any one of claims 1 to 5, wherein R ² , R ³ and R ⁴ in the general formula (1) are ethyl groups. An optical filter comprising the compound according to any one of claims 1 to 6. 8. The optical filter according to claim 7, which is a spectacle lens. A dye composition for spectacle lenses, comprising the compound according to any one of claims 1 to 6.