Compounds, dye compositions, coloring compositions, optical filters, and display devices

Abstract

Provided are a compound having an absorption maximum wavelength near 430 nm, having good light resistance and heat resistance, and having a steep rise on the long wavelength side of the absorption peak, and an optical filter containing the same. 【Solution means】A compound represented by the following general formula (1). JPEG0007857636000024.jpg38156 (In the formula, R 1 is an alkyl group which may have a substituent; R 2 and R 3 are the same or different and are alkyl groups which may have a substituent; R 4 is a cyano group, a halogenated alkyl group or a group represented by SO2NR 6 R 7 represents a group represented by, R 6 and R 7 are the same or different and represent an alkyl group which may have a substituent, or R 6 and R 7 together with the nitrogen atom to which they are attached form a 4- to 7-membered nitrogen-containing heterocyclic group which may have a substituent, and one of the carbon atoms forming the heterocyclic group may be replaced by an oxygen atom; R 5 is a cyano group or a group represented by COOR 8 represents a group represented by, R 8 represents a cyclic alkyl group which may have a substituent.)

Description

[Technical Field]

[0001] This invention relates to compounds. More specifically, it relates to compounds that can be used as dyes. Furthermore, this invention relates to dye compositions, coloring compositions, optical filters, and display devices, etc. [Background technology]

[0002] Optical filters are used to cut out specific wavelengths of light from lighting devices, display devices, and natural light. Such optical filters utilize compounds that can absorb light of specific wavelengths. For example, Patent Document 1 describes an optical film containing a compound that absorbs visible light around 400 nm. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2019-8292 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] Materials used in optical filters are required to have good durability, such as light resistance. The compound described in Patent Document 1 can selectively absorb wavelengths around 400 nm, but there was room for improvement to further enhance its light resistance. In addition, depending on the application of the optical filter, it may be necessary to cut out light around 430 nm while transmitting light on the longer wavelength side of that wavelength. For this reason, there is a need for a compound that has an absorption maximum wavelength around 430 nm and a steep rise of the absorption peak on the longer wavelength side.

[0005] The present invention aims to provide a compound having an absorption maximum wavelength around 430 nm, exhibiting good light resistance and heat resistance, and having a steep rise in the absorption peak on the longer wavelength side, as well as an optical filter containing the same.

Means for Solving the Problem

[0006] As a result of intensive studies to solve the above problems, the inventors have found that the compound represented by the following general formula (1) has an absorption maximum wavelength near 430 nm, has good light resistance and heat resistance, and has a steep rise on the long wavelength side of the absorption peak.

[0007] That is, the present invention relates to the following compounds, dye compositions, coloring compositions, optical filters, display devices, etc., although not limited thereto. 〔1〕A compound represented by the following general formula (1).

[0008]

Chemical formula

[0010] According to the present invention, it is possible to provide a compound having an absorption maximum wavelength around 430 nm, good light resistance and heat resistance, and a steep rise in the absorption peak on the longer wavelength side, as well as an optical filter containing the same. [Modes for carrying out the invention]

[0011] The compound of the present invention is a compound represented by the following general formula (1).

[0012] [ka]

[0013] (In the formula, R1 R represents an alkyl group which may have substituents, 2 and R 3 R represents an alkyl group which may have substituents, either identical or different, 4 This refers to a cyano group, a halogenated alkyl group, or SO2NR 6 R 7 It represents a group represented by R 6 and R 7 R represents an alkyl group which may have substituents, either identical or different, or 6 and R 7 R 6 and R 7 It forms a 4-7 member nitrogen-containing heterocyclic group which may have substituents together with the nitrogen atom to which it is bonded, and one of the carbon atoms forming the nitrogen-containing heterocyclic group may be replaced by an oxygen atom. R 5 is a cyano group or COOR 8 It represents a group represented by R 8 (This represents a cyclic alkyl group which may have substituents.) In this specification, the compound represented by the above general formula (1) is also referred to as compound (1).

[0014] In general formula (1), R 1 This represents an alkyl group which may have substituents. In the present invention, examples of alkyl groups having 1 to 20 carbon atoms that may have substituents include alkyl groups having substituted atoms. In this specification, unless otherwise specified, the number of carbon atoms in an optionally substituted group refers to the total number of carbon atoms in the group including the substituent. "Optionally substituted" means that the substituent may be substituted.

[0015] Examples of C1-C20 alkyl groups that may have substituents include linear, branched, or cyclic alkyl groups that may have substituents. Linear alkyl groups include, for example, linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, and n-pentadecyl groups; Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl 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, 3-ethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylpropyl group, 1-ethyl-2-methylpropyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group Branched alkyl groups such as 1-ethylpentyl group, 2,4-dimethylpentyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,5,5-trimethylpentyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, 1,1-dimethylhexyl group, 1,1,3,3-tetramethylbutyl group, 3,5,5-trimethylhexyl group, 4-ethyloctyl group, 4-ethyl-4,5-dimethylhexyl group, 1,3,5,7-tetramethyloctyl 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, and 2,2,5,5-tetramethylhexyl group; Examples include cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0016] The substituents in the alkyl group, which may have substituents, are not particularly limited and include, for example, aryl groups having 6 to 10 carbon atoms that may have substituents (phenyl group, naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,4-dichlorophenyl group, 2-bromophenyl group, 2-cyanophenyl group, etc.), linear, branched, or cyclic alkoxy groups having 1 to 8 carbon atoms, amino groups, mono- or di- Examples include alkylamino groups (alkyl groups have 1 to 8 carbon atoms), halogen atoms, cyano groups, hydroxyl groups, nitro groups, carboxyl groups, alkoxycarbonyl groups with 1 to 8 carbon atoms, acyl groups with 2 to 12 carbon atoms (e.g., acetyl group, propionyl group, butyryl group, valeryl group, pivaloyl group, acryloyl group, methacryloyl group, benzoyl group, toluyl group, cinnamoyl group, anisoyl group, naphthoyl group, etc.), acyloxy groups with 2 to 12 carbon atoms, and alkenyl groups with 2 to 10 carbon atoms (e.g., vinyl group, 1-propenyl group, allyl group, butenyl group, styryl group, etc.). Examples of substituents in a cyclic alkyl group that may have substituents include linear or branched alkyl groups having 1 to 10 carbon atoms (e.g., methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, etc.). When an alkyl group has substituents, if there are two or more substituents, each substituent may be the same or different. In one embodiment, the substituents on the alkyl group are preferably halogen atoms, or optionally substituted C6-C10 aryl groups. Preferred examples of substituents on the cyclic alkyl group include C1-C6 linear or branched alkyl groups.

[0017] In the present invention, examples of halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms, with fluorine atoms being preferred.

[0018] In general formula (1), R 1 R preferably represents an alkyl group having 1 to 10 carbon atoms, which may have substituents. 1 As the alkyl group in R, a linear or branched alkyl group is preferred. 1 In this, the substituents on the alkyl group are preferably a phenyl group which may have substituents, or an alkoxycarbonyl group having 1 to 10 carbon atoms (such as a methoxycarbonyl group or an ethoxycarbonyl group), and more preferably a phenyl group. 1 Preferably, an alkyl group having 1 to 6 carbon atoms is preferred, an alkyl group having 1 to 4 carbon atoms is more preferred, and an alkyl group having 1 to 3 carbon atoms is even more preferred, and the alkyl group may have substituents or a phenyl group. In one embodiment, R 1 It is more preferable that this represents an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms having a phenyl group, it is even more preferable that this represents an alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms having a phenyl group, it is even more preferable that this represents an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 3 carbon atoms having a phenyl group, it is particularly preferable that this represents a methyl group, an ethyl group, or a benzyl group, and it is most preferable that this represents a methyl group.

[0019] In general formula (1), R 2 and R 3 R represents an alkyl group that may have substituents, either identical or different. 2 and R 3 As the alkyl group in R, a linear or branched alkyl group is preferred. 2 and R 3 R is preferably the same or different, representing an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, even more preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group or an ethyl group, and most preferably a methyl group. In one embodiment, R 2 and R3 are preferably the same group.

[0020] In general formula (1), R 4 represents a cyano group, a halogenated alkyl group or a group represented by SO2NR 6 R 7 represents a group represented by. R 6 and R 7 are the same or different and each represents an alkyl group which may have a substituent, or R 6 and R 7 form, together with the nitrogen atom to which R 6 and R 7 are bonded, a 4- to 7-membered nitrogen-containing heterocyclic group which may have a substituent, and one of the carbon atoms forming the nitrogen-containing heterocyclic group may be replaced by an oxygen atom. R 4 The halogenated alkyl group in is preferably a halogenated alkyl group having 1 to 6 carbon atoms, more preferably a halogenated alkyl group having 1 to 4 carbon atoms, still more preferably a halogenated alkyl group having 1 to 3 carbon atoms, and particularly preferably a halogenated alkyl group having 1 to 2 carbon atoms. As the halogenated alkyl group, a linear or branched halogenated alkyl group is preferred. As the halogenated alkyl group, a fluorinated alkyl group and a chlorinated alkyl group are preferred, and a fluorinated alkyl group is more preferred. As the halogenated alkyl group in R 4 a fluorinated alkyl group having 1 to 4 carbon atoms is still more preferred, a fluorinated alkyl group having 1 to 2 carbon atoms is particularly preferred, and a trifluoromethyl group is most preferred.

[0021] In the group represented by SO2NR 6 R 7 R 6 and R 7 are the same or different and each represents an alkyl group having 1 to 6 carbon atoms, or R 6 and R 7 preferably form, together with the nitrogen atom to which R 6 and R 7 are bonded, a pyrrolidyl group, a piperidyl group or a morpholyl group. In one embodiment, R 6 and R 7It is preferable that they are the same group. 6 and R 7 As the alkyl group in R, a linear or branched alkyl group is preferred. 6 and R 7 In this context, the alkyl group which may have substituents is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, even more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, or a tert-butyl group, and particularly preferably an ethyl group or an n-butyl group. In one embodiment, R 4 This refers to a cyano group, a trifluoromethyl group, or SO2NR 6 R 7 It represents a group represented by R 6 and R 7 It is particularly preferable that this represents an n-butyl group.

[0022] In general formula (1), R 5 is a cyano group or COOR 8 This represents the group represented by R. 8 This represents a cyclic alkyl group which may have substituents. R 8 It is preferable that this represents a cyclic alkyl group having 3 to 6 carbon atoms, which may have a linear or branched alkyl group having 1 to 6 carbon atoms; more preferably a cyclohexyl group having a linear or branched alkyl group having 1 to 4 carbon atoms; even more preferably a cyclohexyl group having a linear or branched alkyl group having 1 to 4 carbon atoms; and particularly preferably a 2,6-di-tertbutyl-4-methylcyclohexyl group.

[0023] In one embodiment, the compound of the present invention is, in general formula (1), R 1 R represents a methyl group, an ethyl group, or a benzyl group. 2 and R 3 R represents a methyl group or an ethyl group, either identical or different. 4 This refers to a cyano group, a trifluoromethyl group, or SO2NR 6 R 7 It represents a group represented by R 6 and R7 It is preferable that the compound represents an n-butyl group. 5 COOR 8 When representing a group represented by R, 8 It is preferable that R represents a cyclohexyl group which may have a linear or branched alkyl group having 1 to 4 carbon atoms. Examples of such compounds include compounds 1-1 to 1-6 produced in the examples. In the compound of the present invention, in general formula (1), R 1 , R 2 and R 3 represents a methyl group, R 4 represents a trifluoromethyl group, R 5 Compounds representing the cyano group are more preferred.

[0024] The method for producing the compound of the present invention will be described below with an example of a synthesis method, but the method for producing the compound of the present invention is not limited to the method described below. Furthermore, when carrying out the reaction described later, functional groups other than the site in question may be protected in advance with an appropriate protecting group as needed, and then deprotected at an appropriate stage.

[0025] Compounds represented by general formula (1) can be synthesized, for example, by the reaction shown below.

[0026] [ka]

[0027] Compound (1) can be obtained by reacting a compound represented by the general formula (2) above (compound (2)) with a compound represented by the general formula (3) (compound (3)). R in general formula (2) 1 , R 2 , R 3 and R 4 , and these preferred embodiments include R in general formula (1). 1 , R 2 , R 3 and R 4 , and the same as these preferred embodiments. R in general formula (3)5 and a preferred embodiment thereof is R in general formula (1). 5 And the same as the preferred embodiment thereof.

[0028] The reaction conditions for reacting compound (2) and compound (3) are not particularly limited, but the reaction is usually carried out in a solvent, and an acid or base may be present in the reaction system. The acid is not particularly limited and examples include acid anhydrides such as acetic anhydride and propionic anhydride, hydrochloric acid, sulfuric acid, phosphorus oxychloride, phosphorus trichloride, polyphosphate, p-toluenesulfonic acid (which may be in hydrate form), acetic acid, etc. Two or more types may be used in combination, and if the acid is in liquid form, it may be used as a solvent. The base is not particularly limited and examples include inorganic bases such as sodium carbonate, potassium carbonate, sodium hydroxide, and potassium hydroxide; and organic bases such as triethylamine, diisopropylethylamine, DBU® (diazabicycloundecene), piperidine, and pyrrolidine. Two or more bases may be used in combination, and if the base is liquid, it may be used as a solvent. The amount of acid or base used may be a catalytic amount or an excess amount.

[0029] The solvent can be any solvent that is inert to the reaction and is not particularly limited. Examples include methanol, ethanol, propanol, butanol, pentanol, hexanol, acetone, acetonitrile, toluene, xylene, dimethylformamide, N-methylmorpholine, dimethyl sulfoxide, dimethylacetamide, pyridine, tetrahydrofuran, etc., and as mentioned above, acids or bases can also be used as solvents. The reaction temperature can be 5 to 100°C, with 10 to 50°C being preferred. The reaction time can be 0.5 to 48 hours, with 1 to 24 hours being preferred.

[0030] Compound (1) can also be synthesized by the reaction shown below.

[0031] [ka]

[0032] Compound (1) can also be obtained by reacting a compound represented by the above general formula (4) (compound (4)) with a compound represented by the general formula (5) (compound (5)). In general formula (4), X - Examples include halide ions, methanesulfonate ions, ethanesulfonate ions, toluenesulfonate ions, trifluoromethanesulfonate ions, tetrafluoroborate ions, etc. R in general formula (4) 1 , R 2 , R 3 and R 4 , and these preferred embodiments include R in general formula (1). 1 , R 2 , R 3 and R 4 , as well as the same as these preferred embodiments. In general formula (5), R can be any group that exhibits electron-donating properties, such as alkyl groups like methyl and ethyl. 5 and a preferred embodiment thereof is R in general formula (1). 5 And the same as the preferred embodiment thereof.

[0033] The reaction conditions for reacting compound (4) and compound (5) are not particularly limited, but the reaction is usually carried out in a solvent. The solvent can be any solvent that is inert to the reaction and is not particularly limited. Examples include methanol, ethanol, propanol, butanol, pentanol, hexanol, acetone, acetonitrile, toluene, xylene, dimethylformamide, N-methylmorpholine, dimethyl sulfoxide, dimethylacetamide, pyridine, tetrahydrofuran, and the like. The reaction temperature can be 5 to 100°C, with 10 to 50°C being preferred. The reaction time can be 0.5 to 48 hours, with 1 to 24 hours being preferred.

[0034] The isolation and purification of each product in the above manufacturing method can be carried out by appropriately combining methods commonly used in organic synthesis, such as filtration, extraction, washing, drying, concentration, crystallization, and various types of chromatography. Furthermore, intermediates can be subjected to the next reaction without any special purification.

[0035] If geometric isomers exist in the compounds of the present invention, the present invention encompasses all of those geometric isomers, as well as tautomers. Furthermore, if one or more chiral carbon atoms exist in the compounds of the present invention, the present invention encompasses compounds in which each chiral carbon atom is in an R configuration, an S configuration, and any combination thereof. Moreover, the present invention also encompasses racemic compounds, racemic mixtures, single enantiomers, and diastereomer mixtures thereof.

[0036] Compound (1) of the present invention is a compound that absorbs violet to indigo light around 430 nm. Specifically, it is preferable that the absorption maximum wavelength (λmax) is 420 to 440 nm. Such a compound can be preferably used, for example, in articles intended to reduce blue light. When the absorption maximum wavelength is 420 to 440 nm and the rise on the long-wavelength side of the absorption spectrum is steep, it is possible to efficiently absorb violet to indigo light while transmitting blue light. Such a compound is suitable for optical filters and the like. The absorption maximum wavelength of compound (1) of the present invention is more preferably 425 to 438 nm, and even more preferably 427 to 436 nm. The absorption maximum wavelength can be determined as the wavelength of the absorption maximum peak obtained by measuring the absorption spectrum of a chloroform solution of the compound with an ultraviolet-visible spectrophotometer.

[0037] Compound (1) of the present invention exhibits a steep rise in the absorption peak on the longer wavelength side. An indicator of a steep rise in the absorption peak on the longer wavelength side is a small ratio (100 × HWHM / FWHM) of the ratio of the full width at half maximum (HWHM) of the absorption peak on the longer wavelength side to the full width at half maximum (FWHM) of the absorption peak. In this specification, the full width at half maximum (FWHM) is the difference (nm) in wavelengths between two points at an absorption peak where the absorbance is half the value of the absorption maximum wavelength (λmax). The full width at half maximum (FWHM) is calculated using the following formula. Full width at half maximum (FWHM) = λ H1 / 2 -λ S1 / 2 In the above formula, λ H1 / 2 The absorbance at that wavelength is half the absorbance at λmax, and λ H1 / 2 > Represents the wavelength at which λmax occurs. S1 / 2 The absorbance at that wavelength is half the absorbance at λmax, and λmax > λ S1 / 2 This represents the wavelength at which absorption is maximum. λmax is the absorption maximum wavelength in chloroform solution between 300 and 800 nm.

[0038] In this specification, the half width at half maximum (HWHM) on the longer wavelength side of the absorption peak is defined as the wavelength (λ) at which the absorbance is halved on the longer wavelength side of the absorption maximum wavelength of the absorption spectrum. H1 / 2 This refers to the distance (nm) between the wavelength and the maximum absorption wavelength, and can be calculated using the following formula. The full width at half maximum (HWHM) on the long wavelength side is λ H1 / 2 -λmax In the above formula, λ max represents the absorption maximum wavelength in the chloroform solution, λ H1 / 2 The absorbance at that wavelength is half the absorbance at λmax, and λ H1 / 2 > Represents the wavelength at which λmax occurs.

[0039] The smaller the ratio of the full width at half maximum (HWHM) of the absorption peak on the longer wavelength side (100 × HWHM / FWHM) to the full width at half maximum (FWHM) of the absorption peak, the steeper the rise of the absorption peak on the longer wavelength side. As an indicator of a steep rise of the absorption peak on the longer wavelength side, compound (1) of the present invention preferably has the above ratio (100 × HWHM / FWHM) of 30 or less, and more preferably 28 or less. Compounds having the absorption spectrum described above have a steep rise on the longer wavelength side of the absorption peak, allowing light on the longer wavelength side of the absorption peak to pass through while efficiently absorbing light at wavelengths near the absorption peak. Such compounds are suitable for optical filters and the like. The full width at half maximum (FWHM) and the long-wavelength side FWHM can be determined from the absorption maximum peak obtained by measuring the absorption spectrum of a chloroform solution of the compound with an ultraviolet-visible spectrophotometer.

[0040] The compound (1) of the present invention preferably has little effect on the transmittance of blue light. As an indicator of having little effect on the transmittance of blue light, the relative value of the absorbance at 460 nm, when the absorbance at the absorption maximum wavelength (λmax) is set to 100, is preferably, for example, 5 or less, more preferably 4 or less, even more preferably 3 or less, and particularly preferably 2 or less. When the absorption maximum wavelength is around 430 nm, if the relative value of the absorbance at 460 nm, when the absorbance at the absorption maximum wavelength is set to 100, is, for example, 5 or less, it will not easily hinder the transmission of blue light. By using such a compound, it is possible to manufacture an optical filter that can absorb wavelengths shorter than blue without impairing the transmittance of blue light. By cutting out light around 430 nm without impairing the transmittance of blue light, effects such as improved anti-glare and anti-reflection of displays can be expected. The relative absorbance at 460 nm, with the absorbance at the absorption maximum wavelength set to 100, can be determined from the absorption maximum peak obtained by measuring the absorption spectrum of a chloroform solution of the compound using a UV-Vis spectrophotometer.

[0041] Compound (1) of the present invention has good heat resistance and light resistance. The thermal decomposition temperature of compound (1) is preferably 205°C or higher, more preferably 210°C or higher, for example, even more preferably 250-400°C, and particularly preferably 300-400°C. The thermal decomposition temperature can be measured using a thermogravimetric analyzer by the method described in the examples. Light resistance can be evaluated by the method described in the examples.

[0042] Compound (1) of the present invention is preferably a compound that is soluble 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 mixtures of two or more of these. Compound (1) of the present invention is preferably soluble in at least one of the above organic solvents at a concentration of 0.1% by mass or more, for example, preferably soluble at a concentration of 0.1% by mass or more and 50% by mass or less, more preferably soluble at a concentration of 1% by mass or more and 40% by mass or less, and even more preferably soluble at a concentration of 2% by mass or more and 30% by mass or less. More preferably, the solubility in organic solvents at 20°C is within this range. Having solubility in organic solvents within this range is preferable because it allows for good manufacturability when compound (1) of the present invention is used, for example, in the manufacture of optical filters.

[0043] Compound (1) of the present invention has the above-described properties and can therefore be suitably used as a dye compound.

[0044] Compound (1) of the present invention can be mixed with, for example, a resin to form a pigment composition. The pigment composition is suitably used as a coloring composition. Pigment compositions and coloring compositions containing compound (1) of the present invention are also included in the present invention. The above resins are not particularly limited, and thermoplastic resins, photocurable resins, thermosetting resins, etc., can be appropriately selected depending on the application of the colored composition. Examples include acrylic resins, polycarbonate resins, polystyrene resins, low-density polyethylene resins, polypropylene resins, polyurethane resins, polyamide resins, polyacetal resins, polyphenylene sulfide resins, polyethylene terephthalate resins, polybutylene terephthalate resins, polycycloolefin resins, polysulfone resins, polyethersulfone resins, fluororesins, silicone resins, polyester resins, epoxy resins, phenolic resins, and melamine resins. These may be used individually or in combination of two or more.

[0045] The amount of compound (1) of the present invention in the dye composition is preferably 0.001 to 50% by mass, and more preferably 0.01 to 40% by mass, relative to the total solid content of the dye composition.

[0046] The dye composition may contain optional components other than compound (1) and resin of the present invention, depending on its intended use. Examples of optional components include antioxidants, defoamers, other dyes (dyes, pigments, etc.), ultraviolet absorbers, infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers, and the like. The method for producing the pigment composition is not particularly limited; for example, the compound (1) of the present invention and the resin, along with any optional components that may be added, may be mixed.

[0047] Compound (1) of the present invention and dye compositions containing the same are suitably used, for example, in the manufacture of optical filters and the like. Optical filters and the like containing compound (1) of the present invention are also included in the present invention. The optical filter only needs to contain compound (1) of the present invention, and its composition is not particularly limited. Optical filters are not particularly limited and include, for example, lenses such as eyeglass lenses, color filters, color correction filters, color conversion filters, and light absorption filters. Eyeglasses include sunglasses and sports goggles. These optical filters can be suitably used in eyeglasses (including sunglasses and goggles), imaging devices, lighting equipment, display devices, etc.

[0048] The optical filter may contain compound (1) of the present invention and may, for example, have a support, similar to conventional filters, and optionally have an optical functional layer. In the optical filter, it is preferable that compound (1) of the present invention is contained in the support or the optical functional layer.

[0049] The composition of the support and the optical functional layer is not particularly limited. For example, the support is usually formed using a transparent resin. Examples of transparent resins include cyclic olefin resins, aromatic polyether resins, polyimide resins, fluorene polycarbonate resins, fluorene polyester resins, polycarbonate resins, polyamide (aramid) resins, polyarylate resins, polysulfone resins, polyethersulfone resins, poly-paraphenylene resins, polyamide-imide resins, polyethylene naphthalate (PEN) resins, fluorinated aromatic polymer resins, (modified) acrylic resins, epoxy resins, polyurethane resins, polythiourethane resins, episulfide resins, and polyolefin resins.

[0050] The method for manufacturing an optical filter is not particularly limited. For example, as a method for forming an optical functional layer containing compound (1) of the present invention on a support, one method is to dissolve or disperse compound (1) of the present invention and a binder resin, etc., in a solvent, and then form a coating film on the support by a coating method such as dip coating, air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, spin coating, or extrusion coating. The solvent is not particularly limited, but examples include the organic solvents mentioned above.

[0051] Furthermore, as a method for producing an optical functional layer or support containing compound (1) of the present invention, compound (1) of the present invention may be mixed with a photocurable resin and / or a thermosetting resin and a photopolymerization initiator and / or a thermal polymerization initiator, and then a cured film may be formed by light irradiation and / or heat treatment, which may be used as an optical functional layer or support.

[0052] Optical filters, such as color filters, color conversion filters, and light absorption filters, can be suitably used in display devices (e.g., liquid crystal displays, organic EL displays), imaging devices, and the like. A display device equipped with the above-mentioned optical filters is also one of the present inventions. The display device only needs to be equipped with the above-mentioned optical filters, and its configuration is not particularly limited. [Examples]

[0053] The following are examples illustrating the present invention in more detail, but the present invention is not limited to these examples.

[0054] In the following examples, the instruments used to measure the physical properties of the obtained compounds are as follows: ( 1 (H-NMR) JEOL Ltd. JNM-ECZ400S (400MHz)

[0055] In Examples 1-6 and Comparative Examples 1-3, compounds represented by the following general formula (1) were synthesized.

[0056] [ka]

[0057] For compounds 1-1 to 1-6 prepared in Examples 1-6 and comparative compounds 1-3 prepared in Comparative Examples 1-3, R 1 , R 2 , R 3 , R 4 and R 5 The results are shown in Table 1 below. Comparative compounds 4 and 5, which were prepared in Comparative Examples 4 and 5, are also shown in Table 1.

[0058] [Table 1]

[0059] In Table 1, Me represents a methyl group, Et represents an ethyl group, Bn represents a benzyl group, and Bu and n-Bu represent n-butyl groups. t-Bu represents a tert-butyl group. Formula (A) in Table 1 indicates a group represented by the following formula (A).

[0060] [ka]

[0061] In formula (A) above, * indicates a bonding site with general formula (1). t-Bu represents a tert-butyl group, and Me represents a methyl group. Compounds 1-1 to 1-5 shown in Examples 1 to 5 were synthesized by the following reaction.

[0062] [ka]

[0063] Table 2 shows the compounds represented by the above general formula (2) (compound (2)) and the compound represented by the above general formula (3) (compound (3)) used in the production of compounds 1-1 to 1-5.

[0064] [Table 2]

[0065] Compound 2-1 has R in general formula (2). 1 , R 2 and R 3 R represents a methyl group. 4 This is a compound in which R represents a trifluoromethyl group. Compound 2-2 has R in general formula (2). 1 R represents an ethyl group, 2 and R 3 R represents a methyl group. 4This is a compound in which the cyano group is represented. Compounds 2-3 have R in general formula (2). 1 represents the benzyl group, R 2 and R 3 R represents a methyl group. 4 This is a compound that represents a trifluoromethyl group. Compound 3-1 has R in general formula (3). 5 This is a compound representing the group shown in formula (A) above.

[0066] Compounds 1-6 shown in Example 6 were synthesized by the following reaction. The compound represented by the following general formula (4) (compound (4)) and the compound represented by the following general formula (5-1) (compound (5-1)) are shown in Table 3.

[0067] [ka]

[0068] [Table 3]

[0069] Compound 4-1 has R in general formula (4). 1 , R 2 and R 3 R represents a methyl group. 4 This is a compound in which the SO2NBu2 group is represented. Compound 5-1 has the following characteristics in general formula (5-1): 5 This is a compound that represents a cyano group.

[0070] <Example 1> Preparation of Compound 1-1 The compound represented by the following formula (Compound 1-1) was synthesized.

[0071] [ka]

[0072] Synthesis of 5-(trifluoromethyl)-1,2,3,3-tetramethylindolinium iodide 5-(trifluoromethyl)-1,2,3,3-tetramethylindolinium iodide was synthesized in the same manner as described in The Journal of Organic Chemistry, 1995, 60(8), 2411.

[0073] Synthesis of 5-(trifluoromethyl)-1,3,3-trimethyl-2-methyleneindoline 37 g of 5-(trifluoromethyl)-1,2,3,3-tetramethylindolinium iodide, 150 mL of water, 150 mL of toluene, and 16.7 g of aqueous NaOH solution were charged into a reaction flask. After stirring at room temperature for 2 hours, the organic layer was washed with water and concentrated under reduced pressure to obtain 24.4 g of 5-(trifluoromethyl)-1,3,3-trimethyl-2-methyleneindoline.

[0074] Synthesis of Compound 2-1 24 g of 5-(trifluoromethyl)-1,3,3-trimethyl-2-methyleneindoline and 100 mL of dimethylformamide (DMF) were placed in a reaction flask, and 37 g of phosphorus oxychloride (Tokyo Chemical Industries, Ltd.) was added dropwise under an ice bath. The mixture was heated to approximately 55°C, stirred for 70 minutes, and then cooled to room temperature. The reaction mixture was drained into an aqueous sodium hydroxide solution, and the precipitated crystals were collected by filtration. The resulting wet cake was recrystallized with isopropyl alcohol (IPA) / water, dried, and 22 g of compound 2-1 was obtained.

[0075] Synthesis of compound 1-1 In a reaction flask, 13.5 g of compound 2-1, 4.7 g of malononitrile (Tokyo Chemical Industries, Ltd.), 5.6 g of acetic anhydride, and 50 mL of toluene were charged. The mixture was stirred at approximately 65°C for 3 hours, then at approximately 80°C for 4 hours, and finally allowed to cool to room temperature. The precipitated crystals were filtered and the resulting wet cake was recrystallized with DMF / methanol and dried to obtain 12 g of compound 1-1. 1H NMR (400MHz, CDCl3): δ(ppm)=7.86(d,1H),7.62(dd,1H),7.49(d,1H),7.00(d,1H),5.89(d,1H),3.42(s,3H),1.64(s,6H).

[0076] <Example 2> Preparation of Compound 1-2 Compounds represented by the following formulas (compounds 1-2) were synthesized. In the following formulas, t-Bu represents a tert-butyl group.

[0077] [ka]

[0078] Synthesis of Compound 3-1 Compound 3-1 was synthesized in the same manner as described in Japanese Patent Publication No. 2000-310841.

[0079] Synthesis of Compounds 1-2 Compound 1-2 was synthesized in the same manner as compound 1-1, except that malononitrile was replaced with compound 3-1. 1 H NMR (400MHz, CDCl3): δ(ppm)=8.38(d,1H),7.59(dd,1H),7.47(d,1H),6.92(d,1H),5.88(d,1H),5.8 3(s,1H),3.38(s,3H),1.67(s,6H),1.66-1.49(m,3H),1.42-1.19(m,4H),1.06(d,3H),0.90(s,18H).

[0080] <Example 3> Manufacturing of Compounds 1-3 Compounds represented by the following formulas (compounds 1-3) were synthesized. In the following formulas, Et represents an ethyl group.

[0081] [ka]

[0082] Synthesis of 1-ethyl-5-cyano-2,3,3-trimethylindolinium iodide 1-ethyl-5-cyano-2,3,3-trimethylindolinium iodide was synthesized in the same manner as described in Japanese Patent Publication No. 2013-199536.

[0083] Synthesis of compound 2-2 Compound 2-2 was synthesized in the same manner as in the synthesis of compound 2-1, except that 5-(trifluoromethyl)-1,2,3,3-tetramethylindolinium iodide was replaced with 1-ethyl-5-cyano-2,3,3-trimethylindolinium iodide.

[0084] Synthesis of Compounds 1-3 Compound 1-3 was synthesized in the same manner as compound 1-1, except that compound 2-1 was replaced with compound 2-2. 1 H NMR (400MHz, CDCl3): δ(ppm)=7.85(d,1H),7.64(dd,1H),7.51(d,1H),6.97(d,1H),5.93(d,1H),3.89(q,2H),1.62(s,6H),1.35(t,3H).

[0085] <Example 4> Preparation of Compounds 1-4 Compounds represented by the following formulas (compounds 1-4) were synthesized. In the following formulas, Ph represents a phenyl group and t-Bu represents a tert-butyl group.

[0086] [ka]

[0087] Synthesis of 1-benzyl-5-(trifluoromethyl)-3,3-dimethyl-2-methyleneindoline 1-benzyl-5-(trifluoromethyl)-3,3-dimethyl-2-methyleneindoline was synthesized in the same manner as described in CN115926156.

[0088] Synthesis of Compounds 2-3 Compound 2-3 was synthesized in the same manner as in the synthesis of compound 2-1, except that 5-(trifluoromethyl)-1,3,3-trimethyl-2-methyleneindoline was replaced with 1-benzyl-5-(trifluoromethyl)-3,3-dimethyl-2-methyleneindoline.

[0089] Synthesis of Compounds 1-4 Compound 1-4 was synthesized in the same manner as in the synthesis of compound 1-1, except that compound 2-1 was replaced with compound 2-3 and malononitrile was replaced with compound 3-1. 1 H NMR (400MHz, CDCl3): δ(ppm)=8.37(d,1H),7.51-7.53(m,2H),7.28-7.39(m,3H),7.21(d,2H),6.92(d,1H),5.97(d,1 H),5.81(s,1H),5.00(s,2H),1.71(s,6H),1.60-1.66(m,1H),1.36(q,2H),1.19(dd,2H),1.05(d,3H),0.89(s,20H).

[0090] <Example 5> Manufacturing of Compounds 1-5 Compounds represented by the following formulas (compounds 1-5) were synthesized. In the following formulas, Ph represents a phenyl group.

[0091] [ka]

[0092] Synthesis of Compounds 1-5 Compound 1-5 was synthesized in the same manner as in the synthesis of compound 1-1, except that compound 2-1 was replaced with compound 2-3. 1 H NMR (400MHz, CDCl3): δ(ppm)=7.84(d,1H),7.57(dd,1H),7.53(s,1H),7.36(m,3H),7.18(d,2H),7.00(d,1H),5.97(d,1H),5.03(s,2H),1.68(s,6H).

[0093] <Example 6> Manufacturing of Compounds 1-6 Compounds represented by the following formulas (compounds 1-6) were synthesized. In the following formulas, n-Bu represents an n-butyl group.

[0094] [ka]

[0095] Synthesis of N,N-di-n-butyl-4-hydrazinobenzenesulfonamide N,N-di-n-butyl-4-hydrazino-benzenesulfonamide was synthesized in the same manner as described in US2902366.

[0096] Synthesis of N,N-di-n-butyl-2,3,3-trimethylindorenine-5-sulfonamide In a reaction flask, 10 g of N,N-di-n-butyl-4-hydrazinobenzenesulfonamide, 3.0 g of 3-methyl-2-butanone, 6.7 g of p-toluenesulfonic acid monohydrate (Kishida Chemical Co., Ltd.), and 70 mL of toluene were charged and the mixture was reacted at 110°C for 5 hours. After cooling, the reaction mixture was filtered, the filtrate was washed with dilute NaOH aqueous solution, washed with water, and the organic layer was separated and concentrated under reduced pressure to obtain 11 g of N,N-di-n-butyl-2,3,3-trimethylindorenine-5-sulfonamide.

[0097] Synthesis of Compound 4-1 In a reaction flask, 11.6 g of N,N-di-n-butyl-2,3,3-trimethylindorenine-5-sulfonamide, 4.1 mL of methyl iodide (Tokyo Chemical Industries, Ltd.), and 40 mL of acetonitrile were charged and the mixture was reacted at 40°C for 18 hours. Ethyl acetate was added, the precipitate was filtered and dried to obtain 9.0 g of compound 4-1.

[0098] Synthesis of compounds 1-6 In a reaction flask, 11.5 g of compound 4-1, 0.74 g of ethoxymethylene malononitrile (Sigma-Aldrich), and 6 mL of pyridine were charged and the mixture was reacted at approximately 80°C for 3 hours. After cooling, the reaction mixture was drained into water and the precipitate was filtered. The filtered crude product was washed with methanol and dried to obtain 1.2 g of compound 1-6. 1 H NMR(400MHz,CDCl3):δ(ppm)=7.85(d,1H),7.78(dd,1H),7.68(d,1H),6.99(d,1H),5.90( d,1H),3.42(s,3H),3.12(t,4H),1.63(s,6H),1.49(quin,4H),1.29(m,4H),0.89(m,6H).

[0099] <Comparative Example 1> Preparation of comparative compound 1 In a reaction flask, 6 g of 2-(1,3,3-trimethylindoline-2-ylidene)acetaldehyde (Tokyo Chemical Industries, Ltd.), 2.2 g of malononitrile (Tokyo Chemical Industries, Ltd.), 3.4 g of acetic anhydride, and 30 mL of toluene were charged and the mixture was reacted at 60°C for 2 hours. After cooling, the precipitate was filtered and dried to obtain 6.3 g of comparative compound 1.

[0100] <Comparative Example 2> Preparation of comparative compound 2 6 g of 2-(1,3,3-trimethylindoline-2-ylidene)acetaldehyde (Tokyo Chemical Industries, Ltd.), 3.4 g of ethyl cyanoacetate (Tokyo Chemical Industries, Ltd.), and 60 mL of acetic anhydride were charged into a reaction flask, and the mixture was reacted at approximately 65°C for 2 hours. After cooling, the reaction solution was drained into water, and the precipitate was filtered out. The resulting crude product was purified with a solvent and dried to obtain 5.7 g of comparative compound 2.

[0101] <Comparative Example 3> Preparation of comparative compound 3 Synthesis of 5-nitro-2,3,3-trimethyl-Nn-octylindolinium iodide 5-nitro-2,3,3-trimethyl-Nn-octylindlium iodide was synthesized in the same manner as described in US2006223076.

[0102] Synthesis of comparative compound 3 Comparative compound 3 was synthesized in the same manner as in the synthesis of compounds 1-6, except that compound 4-1 was replaced with 5-nitro-2,3,3-trimethyl-Nn-octylindolinium iodide.

[0103] <Comparative Example 4> Manufacturing of comparative compound 4 Comparative compound 4 was synthesized from the compound represented by formula (6) (compound (6)) and the compound represented by formula (7) (compound (7)) by the following reaction. In the following formulas, Et represents an ethyl group, Ph represents a phenyl group, and t-Bu represents a tert-butyl group.

[0104] [ka]

[0105] Compound (7): Synthesis of 3-tert-butylisoxazole-5(4H)-one Compound (7) was obtained in the same manner as described in Journal of Materials Chemistry, 2001, 11(9), 2271.

[0106] Synthesis of comparative compound 4 In a reaction flask, 1.4 g of compound (6), synthesized in reference to Japanese Patent Publication No. 2014-194508, 0.58 g of compound (7), 0.50 g of acetic anhydride, and 6 mL of acetonitrile were charged. A mixture of 0.83 g of triethylamine and 2 mL of acetonitrile was added dropwise at room temperature, and the mixture was stirred overnight at 65°C. After cooling, the reaction mixture was drained into water, the precipitate was filtered, and the resulting crude product was purified and dried to obtain 0.28 g of comparative compound 4.

[0107] <Comparative Example 5> Preparation of comparative compound 5 Comparative compound 5 was synthesized from the compound represented by formula (8) (compound (8)) and the compound represented by formula (9) (compound (9)) by the following reaction. In the following formulas, n-Bu represents an n-butyl group.

[0108] [ka]

[0109] Comparative compound 5 In a reaction flask, 1.5 g of compound (8), synthesized in reference to Japanese Patent Publication No. 2018-188565, 0.92 g of compound (9), synthesized in reference to Japanese Patent Publication No. 2006-008678, a few drops of piperidine, and 10 mL of ethanol were added and the mixture was stirred at 65°C for 1.5 hours. After cooling, the precipitate was filtered and dried to obtain 1.6 g of comparative compound 5.

[0110] The compounds obtained in the examples and comparative examples were evaluated as follows. <Spectroscopic Characteristics Test> Measuring equipment: JASCO Corporation, UV-visible spectrophotometer V-560 (1) Absorption maximum wavelength and full width at half maximum The absorption spectra of the compounds obtained in the examples and comparative examples were measured in chloroform, and the absorption maximum wavelength (λmax), the full width at half maximum (FWHM) of the absorption maximum peak, and the full width at long wavelengths (HWHM) were determined. The full width at half maximum (FWHM) was calculated using the following formula (I). FWHM(nm) = λ H1 / 2 -λ S1 / 2 Equation (I) (In the above formula (I), λ H1 / 2 The absorbance at that wavelength is half the absorbance at λmax, and λ H1 / 2 > Represents the wavelength at which λmax occurs. S1 / 2 The absorbance at that wavelength is half the absorbance at λmax, and λmax > λ S1 / 2 This represents the wavelength at which absorption is maximum. λmax is the absorption maximum wavelength in chloroform solution between 300 and 800 nm.

[0111] The full width at half maximum (HWHM) on the longer wavelength side is calculated by comparing the absorption maximum wavelength (λmax) with the wavelength at which the absorbance is halved on the longer wavelength side of the absorption maximum wavelength in the absorption spectrum (λ H1 / 2 ) was obtained using the following formula (II). HWHM(nm) = λ H1 / 2 -λmax Formula (II) (In the above equation (II), λmax represents the absorption maximum wavelength in the chloroform solution at 300-800 nm, λ H1 / 2 The absorbance at that wavelength is half the absorbance at λmax, and λ H1 / 2 (This represents the wavelength at which λmax occurs.)

[0112] As an indicator of the steep rise of the absorption peak on the longer wavelength side, the ratio of the long-wavelength full width at half maximum (HWHM) to the total full width at half maximum (FWHM) (100 × HWHM / FWHM) was calculated. The value of the above ratio (100 × HWHM / FWHM) was evaluated according to the following criteria. (Evaluation criteria: 100 × HWHM / FWHM) A: 100 × HWHM / FWHM is 30 or less B: 100 × HWHM / FWHM is greater than 30 and less than or equal to 35 C:100×HWHM / FWHM exceeds 35 Table 4 shows the full width at half maximum (FWHM), the full width at long wavelength (HWHM), the (100 × HWHM / FWHM) values, and the evaluation according to the above criteria for the compounds obtained in the examples and comparative examples.

[0113] (2) Absorbance at 460 nm From the absorption spectrum, the relative absorbance at 460 nm was determined, with the absorbance at the absorption maximum wavelength (λmax) set to 100. The relative absorbance at 460 nm was evaluated according to the following criteria. (Evaluation criteria for absorbance at 460 nm) A: Relative intensity is 5 or less B: Relative intensity greater than 5 and less than or equal to 10 C: Relative intensity exceeds 10 Table 4 shows the relative absorbance values ​​at 460 nm and their evaluations based on the above criteria.

[0114] [Table 4]

[0115] Compounds 1-1 to 1-6 had a ratio of the full width at half maximum (HWHM) on the longer wavelength side (HWHM) to the full width at half maximum (FWHM) of 30 or less. This indicates that compounds 1-1 to 1-6 have a steep rise in the absorption peak on the longer wavelength side. Furthermore, the relative absorbance value at 460 nm for compounds 1-1 to 1-6 was 5 or less. The comparative example compounds had a higher relative absorbance value at 460 nm than the example compounds. When the absorption maximum wavelength is around 430 nm, a relatively large absorbance at 460 nm results in a gradual change from the peak showing the absorption maximum to the baseline on the longer wavelength side of the absorption maximum wavelength, increasing the portion of the absorption spectrum that overlaps with blue light.

[0116] <Heat resistance> For the compounds obtained in the examples and comparative examples, the weight loss due to thermal decomposition was measured using a Shimadzu Corporation TGA-50 thermogravimetric analyzer under the following measurement conditions, and the temperature at which a 1% weight loss from the initial weight was observed was defined as the decomposition start temperature. (Measurement conditions) Measurements were taken under the following conditions: sample volume 10 mg, heating rate 10°C / min (maximum temperature reached 500°C), nitrogen atmosphere, and flow rate 20 mL / min. Heat resistance was evaluated based on the decomposition initiation temperature according to the following criteria. The results are shown in Table 5. A: Above 300℃ B: 270℃ or higher, but less than 300℃ C: Below 270℃

[0117] <Lightfastness Test> The compounds obtained in the examples and comparative examples were subjected to lightfastness tests. Ten mg of each compound was dissolved in 5 mL of an 8 wt% polymethacrylate toluene solution, and the mixture was applied to a glass substrate by spin coating and dried to produce a thin film with a thickness of 1.5 μm. The fabricated thin film was continuously irradiated with light from a xenon lamp (142 klux) for 24 hours. The transmittance of the thin film before irradiation (0 hours) and after irradiation was measured using a spectrophotometer, and the remaining compound percentage was measured according to the following formula (III). Compound retention rate (%) = {(1-T1) / (1-T0)} × 100 (III) [However, T0 is the transmittance before xenon lamp irradiation, and T1 is the transmittance after xenon lamp irradiation; both T0 and T1 are between 0 and 1.] Note that "transmittance" refers to the transmittance at the absorption maximum wavelength of each compound. The higher the retention rate, the less the compound is decomposed by light, indicating higher lightfastness. Lightfastness was evaluated according to the following criteria. The results are shown in Table 5. A: Compound retention rate of 85% or more B: Compound retention rate is 75% or more, but less than 85%. C: Compound retention rate is 65% or more, but less than 75%. D: Compound retention rate is less than 65% Measuring equipment: JASCO Corporation, UV-visible spectrophotometer V-570

[0118] [Table 5]

[0119] <Solubility Test> For some of the compounds obtained in the examples, the solubility (mass%) in the solvent at 20°C was measured by the following method. The solvents used were tetrahydrofuran (THF), propylene glycol monomethyl ether acetate (PGMEA), or methyl ethyl ketone (MEK). The compound was weighed into a glass test tube, mixed with a solvent, and dissolved by stirring at 20°C. The state of the solution was visually observed, and the soluble mass concentration was evaluated. The results are shown in Table 6. The solvent used for the solubility evaluation is also shown in Table 6. S: Dissolves at a concentration of 5.0% by mass or more. A: Dissolves at a concentration of 2.0% by mass or more and less than 5.0% by mass. B: Dissolves at a concentration of 1.0% by mass or more and less than 2.0% by mass. C: Only less than 1.0% by mass dissolves.

[0120] [Table 6]

[0121] The compounds of Examples 1 to 6 had an absorption maximum wavelength around 430 nm, exhibited good light resistance and heat resistance, and had a steep rise in the absorption peak on the longer wavelength side.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 (In the formula, R １ This represents an alkyl group or benzyl group having 1 to 6 carbon atoms. R ２ and R ３ These represent alkyl groups having 1 to 6 carbon atoms, which are the same or different. R ４ This represents a fluoride alkyl group having 1 to 4 carbon atoms. R ５ is a cyano group or COOR ８ It represents a group represented by R ８ (This represents a cyclic alkyl group having 3 to 6 carbon atoms, which may have a linear or branched alkyl group having 1 to 6 carbon atoms.)

2. R １ This represents an alkyl group or benzyl group having 1 to 3 carbon atoms. R ２ and R ３ are the same or different and each represents an alkyl group having 1 to 4 carbon atoms, R ４ This represents a fluoride alkyl group having 1 to 2 carbon atoms. R ８ The compound according to claim 1, wherein is a cyclic alkyl group having 3 to 6 carbon atoms, which may have a linear or branched alkyl group having 1 to 4 carbon atoms.

3. R １ This represents a methyl group, an ethyl group, or a benzyl group. R ２ and R ３ These represent a methyl group or an ethyl group, either identical or different. R ４ This represents a trifluoromethyl group, R ８ The compound according to claim 1 or 2, wherein is a cyclohexyl group which may have a linear or branched alkyl group having 1 to 4 carbon atoms.

4. In general formula (1), R １ , R ２ and R ３ represents a methyl group, R ４ represents a trifluoromethyl group, R ５ The compound according to claim 1 or 2, wherein is a cyano group.

5. A dye composition characterized by comprising the compound described in claim 1 or 2.

6. A colored composition characterized by comprising the compound and resin described in claim 1 or 2.

7. An optical filter characterized by containing the compound described in claim 1 or 2.

8. A display device characterized by comprising the optical filter described in claim 7.

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