Compounds and optical filters

Abstract

To provide a compound that can efficiently absorb light near the wavelength 400nm, while absorption of light in the wavelength 500nm is reduced.SOLUTION: Provided is a compound expressed by the following general formula (1). [Formula 1] (in the general formula (1), R1 denotes an alkyl halide group which may have a substituent, R2 denotes an aryl group which may have a substituent, R21, R22, R23 and R24 denote each independently an alkyl group which may have a hydrogen atom and a substituent, an aryl group which may have a substituent, an alkoxycarbonyl group which may have a substituent or an alkylcarbonyl group which may have a substituent.)SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to compounds that can be used as dyes, optical filters containing such compounds, and the like. [Background technology]

[0002] Optical filters are used to cut out specific wavelengths of light from light emitted by lighting devices, display devices, and the like. Such optical filters utilize compounds that can absorb light of specific wavelengths.

[0003] Non-patent documents 1 and 2 disclose a pyrazolone derivative (CAS RN: 93331-50-1) having an absorption maximum wavelength around 400 nm. [Prior art documents] [Non-patent literature]

[0004] [Non-Patent Document 1] Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft. 1962, 295, pp607-615. [Non-Patent Document 2] Helvetica Chimica Acta. 1962, 45, pp1908-1917. [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] In recent years, there has been a demand for optical filters that cut out a specific wavelength of light. For example, there is a need for a compound that can efficiently absorb light around 400 nm while absorbing less light at longer wavelengths, such as 500 nm. The pyrazolone derivative (CAS RN: 93331-50-1) disclosed in Non-Patent Documents 1 and 2 is a dye compound that can be used for optical filter applications. However, the above pyrazolone derivative (CAS RN: 93331-50-1) had room for improvement in further reducing the absorption of 500 nm light.

[0006] The present invention aims to provide a compound that can efficiently absorb light around a wavelength of 400 nm while reducing the absorption of light at a wavelength of 500 nm. [Means for solving the problem]

[0007] The inventors conducted diligent research to solve the above problems and discovered that a compound represented by the following general formula (1) can efficiently absorb light around 400 nm in wavelength, while exhibiting low absorbance of light at 500 nm in wavelength. Based on this finding, the inventors conducted further research and completed the present invention.

[0008] In other words, the present invention is not limited to the following, but relates to the following compounds, etc. <1> A compound represented by the following general formula (1).

[0009] [ka]

[0010] (In general formula (1), R 1 This represents a halogenated alkyl group which may have substituents, R 2 This represents an aryl group which may have substituents, R 21 , R 22 , R 23 and R 24each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxycarbonyl group which may have a substituent or an alkylcarbonyl group which may have a substituent.)

[0011] <2>R in the general formula (1) above 1 is a compound as described in <1> above, which is an alkyl fluoride group. <3>R in the general formula (1) above 2 is a compound as described in <1> or <2> above, which is a group represented by the following general formula (2) or (3).

[0012]

Chemical formula

[0013] (In the general formula (2), R 11a , R 12a , R 13a , R 14a and R 15a each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -COR 101a , -COOR 102a , -CONR 103a R 104a , an alkyl group which may have a substituent or an aryl group which may have a substituent, and R 101a , R 102a , R 103a and R 104a each independently represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent.) * indicates the bonding site with the general formula (1).)

[0014]

Chemical formula

[0015] (In the general formula (3), R 11b , R 12b , R 13b , R 14b , R15b , R 16b and R 17b These are, independently, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and a -COR group. 101b ,-COOR 102b ,-CONR 103b R 104b , represents an alkyl group which may have substituents or an aryl group which may have substituents, R 101b , R 102b , R 103b and R 104b Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates the bonding site with general formula (1).

[0016] <4> In the above general formula (2), R 11a , R 12a , R 13a , R 14a and R 15a Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, as described above. <3> The compounds described above. <5> In the above general formula (3), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, as described above. <3> The compounds described above. <6> In the above general formula (1), R 21 , R 22 , R 23 and R 24 Each of these independently represents a hydrogen atom or an alkyl group which may have a substituent, as described above. <1> ~ <5> A compound listed in any of the following. <7> the above <1> ~ <6> An optical filter characterized by containing any of the compounds described in one of the following. <8> A compound represented by the following general formula (4).

[0017] [ka]

[0018] (In general formula (4), R 1 This represents a halogenated alkyl group which may have substituents, R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b These are, independently, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and a -COR group. 101b ,-COOR 102b ,-CONR 103b R 104b , represents an alkyl group which may have substituents or an aryl group which may have substituents, R 101b , R 102b , R 103b and R 104b Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. <9> In the above general formula (4), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b At least one of the above is a fluorine atom or a group containing a fluorine atom. <8> The compounds described above. [Effects of the Invention]

[0019] According to the present invention, it is possible to provide a compound that can efficiently absorb light around a wavelength of 400 nm while reducing the absorption of light at a wavelength of 500 nm. [Modes for carrying out the invention]

[0020] The compound of the present invention is a compound represented by the following general formula (1). In this specification, the compound represented by the following general formula (1) is also referred to as compound (1).

[0021] [ka]

[0022] (In general formula (1), R 1 This represents a halogenated alkyl group which may have substituents, R 2 This represents an aryl group which may have substituents, R 21 , R 22 , R 23 and R 24 Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxycarbonyl group, or an optionally substituted alkylcarbonyl group.

[0023] In the present invention, the optionally substituted alkyl halide preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 to 2 carbon atoms. In this specification, the carbon number of the optionally substituted group refers to the total carbon number of the group including the substituent. In the present invention, the alkyl group may be linear, branched, or cyclic. A preferred example of a halogenated alkyl group which may have substituents is an alkyl group having 1 to 6 carbon atoms in which some or all of the hydrogen atoms are substituted with halogen atoms. The alkyl halide, which may have substituents, is preferably a linear alkyl halide, and more preferably a linear alkyl halide having 1 to 3 carbon atoms. Examples of halogens in the alkyl halide include fluorine, chlorine, and bromine, with fluorine being preferred.

[0024] In general formula (1), R 1It is preferable that it be an alkyl fluoride. Examples of alkyl fluoride groups include trifluoromethyl group, pentafluoroethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, and 3,3,3-trifluoropropyl group. 1 The trifluoromethyl group and the pentafluoroethyl group are preferred, with the trifluoromethyl group being more preferred.

[0025] In general formula (1), R 21 , R 22 , R 23 and R 24 Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxycarbonyl group, or an optionally substituted alkylcarbonyl group.

[0026] In the present invention, the alkyl group, which may have substituents, preferably has 1 to 20 carbon atoms. Examples of alkyl groups include 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 group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, norbornyl group, and adamantyl group.

[0027] 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 (phenyl group, naphthyl group, etc.), linear, branched, or cyclic alkoxy groups having 1 to 8 carbon atoms, amino groups, mono- or di-alkylamino groups (alkyl groups having 1 to 8 carbon atoms), halogen atoms, cyano groups, hydroxyl groups, nitro groups, carboxyl groups, alkoxycarbonyl groups having 1 to 8 carbon atoms, acyl groups having 2 to 10 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 having 2 to 10 carbon atoms, and alkenyl groups having 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.

[0028] In the present invention, an aryl group which may have substituents may be an aryl group having 6 to 20 carbon atoms which may have substituents. The aryl group is not particularly limited and includes, for example, monocyclic aromatic hydrocarbon groups such as a phenyl group; and polycyclic aromatic hydrocarbon groups such as a naphthyl group, anthracenyl group, naphthacenyl group, pentacenyl group, phenantrenyl group, and pyrenyl group. Among these, a phenyl group and a naphthyl group are preferred as the aryl group, and a phenyl group is more preferred.

[0029] The substituents in the optionally substituted aryl group are not particularly limited and include, for example, halogen atoms, cyano groups, nitro groups, optionally substituted alkoxy groups, optionally substituted alkoxycarbonyl groups, optionally substituted amide groups, optionally substituted alkyl groups, optionally substituted aryl groups, hydroxyl groups, and optionally substituted amino groups (e.g., amino groups, mono- or di-alkylamino groups (alkyl groups having 1 to 8 carbon atoms)). Examples of halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms, with fluorine atoms being preferred. Preferred substituents in the optionally substituted aryl group include, for example, halogen atoms, cyano groups, nitro groups, optionally substituted C1-C8 alkoxy groups, optionally substituted C2-C8 alkoxycarbonyl groups, optionally substituted amide groups, and optionally substituted C1-C8 alkyl groups. When an aryl group has substituents, if there are two or more substituents, each substituent may be the same or different.

[0030] Examples of optionally substituted alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 10 carbon atoms that may have substituents. Preferably, the alkoxycarbonyl group has 2 to 8 carbon atoms.Examples of alkoxycarbonyl groups that may have substituents include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, neopentyloxycarbonyl group, 1,2-dimethylpropyloxycarbonyl group, n-hexyloxycarbonyl group, cyclohexyloxycarbonyl group, 1,3-dimethylbutyloxycarbonyl group, 1-isopropylpropyloxycarbonyl group, 1,2-dimethylbutyloxycarbonyl group, n-heptyloxycarbonyl group, 1,4-dimethylpentyloxycarbonyl group, 2-methyl-1-isopropylpropyloxycarbonyl group, 1-ethyl-3-methylbutyloxycarbonyl group, n-octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, 3-methyl-1-isopropylbutyloxycarbonyl group, 2-methyl-1-isopropyloxycarbonyl group, 1 -tert-butyl-2-methylpropyloxycarbonyl group, n-nonyloxycarbonyl group, methoxymethoxycarbonyl group, methoxyethoxycarbonyl group, ethoxyethoxycarbonyl group, propoxyethoxycarbonyl group, butoxyethoxycarbonyl group, diethylaminoethoxycarbonyl group, methylthioethoxycarbonyl group, methoxypropyloxycarbonyl group, γ-methoxypropoxycarbonyl group, γ-ethoxypropoxycarbonyl group, methoxyethoxyethoxycarbonyl group, ethoxyethoxyethoxycarbonyl group Examples include the nyl group, dimethoxymethoxycarbonyl group, diethoxymethoxycarbonyl group, dimethoxyethoxycarbonyl group, diethoxyethoxycarbonyl group, (3,6,9-oxa)decyloxycarbonyl group, tetrahydrofurfuryloxycarbonyl group, pyranoxycarbonyl group, piperidinooxycarbonyl group, piperidinoethoxycarbonyl group, tetrahydropyrroleoxycarbonyl group, tetrahydropyranmethoxycarbonyl group, tetrahydrothiophenoxycarbonyl group, and cyclohexyloxycarbonyl group.

[0031] Examples of alkylcarbonyl groups that may have substituents include alkylcarbonyl groups having 2 to 10 carbon atoms that may have substituents. Examples of alkylcarbonyl groups that may have substituents include methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, isopropylcarbonyl group, n-butylcarbonyl group, isobutylcarbonyl group, sec-butylcarbonyl group, tert-butylcarbonyl group, n-pentylcarbonyl group, isopentylcarbonyl group, neopentylcarbonyl group, 1,2-dimethylpropylcarbonyl group, n-hexylcarbonyl group, cyclohexylcarbonyl group, and 1 ,3-dimethyl-butylcarbonyl group, 1-isopropylpropylcarbonyl group, 1,2-dimethylbutylcarbonyl group, n-heptylcarbonyl group, 1,4-dimethylpentylcarbonyl group, 2-methyl-1-isopropylpropylcarbonyl group, 1-ethyl-3-methylbutylcarbonyl group, n-octylcarbonyl group, 2-ethylhexylcarbonyl group, 3-methyl-1-isopropylbutylcarbonyl group, 2-methyl-1-isopropylcarbonyl group, 1-tert-butyl 2-methylpropylcarbonyl group, n-nonylcarbonyl group, methoxymethylcarbonyl group, methoxyethylcarbonyl group, ethoxyethylcarbonyl group, propoxyethylcarbonyl group, butoxyethylcarbonyl group, diethylaminoethylcarbonyl group, methylthioethylcarbonyl group, methoxypropylcarbonyl group, γ-methoxypropylcarbonyl group, γ-ethoxypropylcarbonyl group, methoxyethoxyethylcarbonyl group, ethoxyethoxyethylcarbonyl group Examples include dimethoxymethylcarbonyl group, diethoxymethylcarbonyl group, dimethoxyethylcarbonyl group, diethoxyethylcarbonyl group, (3,6,9-oxa)decylcarbonyl group, tetrahydrofurfurylcarbonyl group, pyranylcarbonyl group, piperidinocarbonyl group, piperidinoethylcarbonyl group, tetrahydropyrrolidinylcarbonyl group, tetrahydropyranylmethylcarbonyl group, tetrahydrothienylcarbonyl group, cyclohexylcarbonyl group, and others.

[0032] In general formula (1), R 21, R 22 , R 23 and R 24 each independently preferably represents a hydrogen atom or an alkyl group which may have a substituent, more preferably represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may have a substituent, still more preferably represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and particularly preferably represents a hydrogen atom, a methyl group or an ethyl group. In one embodiment, R 21 and R 24 each independently preferably represents an alkyl group which may have a substituent, more preferably represents an alkyl group having 1 to 3 carbon atoms, and still more preferably represents a methyl group or an ethyl group. R 21 and R 24 particularly preferably represents a methyl group. In one embodiment, R 22 and R 23 preferably represents a hydrogen atom.

[0033] In the above general formula (1), R 2 represents an aryl group which may have a substituent. As the aryl group which may have a substituent in R 2 , a group represented by the following general formula (2) and a group represented by the following general formula (3) are preferable. R 2 is preferably a group represented by the following general formula (2) or (3).

[0034] [Chemical formula]

[0035] (In the general formula (2), R 11a , R 12a , R 13a , R 14a and R 15a each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -COR 101a , -COOR 102a , -CONR 103a R 104a , an alkyl group which may have a substituent or an aryl group which may have a substituent, R101a , R 102a , R 103a and R 104a Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates the bonding site with general formula (1).

[0036] [ka]

[0037] (In general formula (3), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b These are, independently, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and a -COR group. 101b ,-COOR 102b ,-CONR 103b R 104b , represents an alkyl group which may have substituents or an aryl group which may have substituents, R 101b , R 102b , R 103b and R 104b Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates the bonding site with general formula (1).

[0038] The above R 101a , R 102a , R 103a and R 104a Preferably, each is independently an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms. 101b , R 102b , R 103b and R 104b Preferably, each is independently an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms.

[0039] In general formula (2), R11a , R 12a , R 13a , R 14a and R 15a Each of these preferably independently represents a hydrogen atom, a halogen atom, or an alkyl group which may have substituents, and more preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms which may have substituents. The halogen atom is preferably a fluorine atom. R 11a ~R 15a In this, the alkyl group which may have substituents is preferably an alkyl group which may be substituted with a halogen atom, more preferably an alkyl group having 1 to 3 carbon atoms which may be substituted with a halogen atom, even more preferably an alkyl group having 1 to 3 carbon atoms which may be substituted with a fluorine atom, a methyl group, an ethyl group, a trifluoromethyl group, and a pentafluoroethyl group are particularly preferred, and a trifluoromethyl group is most preferred. In one embodiment, R 11a , R 12a , R 13a , R 14a and R 15a Preferably, at least one of these is a fluorine atom or a group containing a fluorine atom. As a group containing a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms is preferred, and a trifluoromethyl group is more preferred.

[0040] In general formula (3), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b Each of these preferably independently represents a hydrogen atom, a halogen atom, or an alkyl group which may have substituents, and more preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms which may have substituents. The halogen atom is preferably a fluorine atom. R 11b ~R 17bIn this, the alkyl group which may have substituents is preferably an alkyl group which may be substituted with a halogen atom, more preferably an alkyl group having 1 to 3 carbon atoms which may be substituted with a halogen atom, even more preferably an alkyl group having 1 to 3 carbon atoms which may be substituted with a fluorine atom, a methyl group, an ethyl group, a trifluoromethyl group, and a pentafluoroethyl group are particularly preferred, and a trifluoromethyl group is most preferred. In one embodiment, R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b Preferably, at least one of these is a fluorine atom or a group containing a fluorine atom. As a group containing a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms is preferred, and more preferred than a trifluoromethyl group.

[0041] In one embodiment, in general formula (1), R 2 It is more preferable that the group is represented by the general formula (2) above. 2 It is preferable that the group is represented by the general formula (2) above, as this results in good light resistance of compound (1). In general formula (1), R 2 Compounds in which the group is represented by the above general formula (2) are compounds represented by the following general formula (10).

[0042] [ka]

[0043] In the above general formula (10), R 1 , R 21 , R 22 , R 23 and R 24 R in general formula (1) 1 , R 21 , R 22 , R 23 and R 24 These are the same as above. R in general formula (10) 11a , R 12a , R 13a , R14a and R 15a This is R in general formula (2). 11a , R 12a , R 13a , R 14a and R 15a These are the same as above.

[0044] Examples of preferred embodiments of compound (1) include, for example, the compound represented by formula (1-1), the compound represented by formula (1-2), the compound represented by formula (1-3), the compound represented by formula (1-4), the compound represented by formula (1-5), and so on. In one embodiment, examples of more preferred embodiments of compound (1) include the compound represented by formula (1-1), the compound represented by formula (1-2), the compound represented by formula (1-3), and the compound represented by formula (1-4), as described below.

[0045] If geometric isomers exist in the compounds of the present invention, the present invention encompasses all of those geometric isomers. 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, a S configuration, or any combination thereof. Moreover, the present invention also encompasses racemic compounds, racemic mixtures, single enantiomers, and diastereomer mixtures thereof.

[0046] The method for producing compound (1) 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.

[0047] The method for producing the compounds of the present invention is not particularly limited and can be obtained by methods that are generally known. For example, a compound represented by the following general formula (1A) (referred to as compound (1A)) can be obtained by reacting a compound represented by the following general formula (11) (compound (11)) with a compound represented by the following general formula (14) (compound (14)).

[0048] [ka]

[0049] R in general formula (1A) 1 , R 2 , R 21 and R 24 R in general formula (1) 1 , R 2 , R 21 and R 24 These are the same as above. R in general formula (1A) 1 , R 2 , R 21 and R 24 The preferred embodiment is the same as that of general formula (1). Compound (1A) is, in the above general formula (1), R 22 and R 23 It is a compound in which the atom is a hydrogen atom.

[0050] [ka]

[0051] R in general formula (11) 21 and R 24 , and these preferred embodiments include R in general formula (1). 21 and R 24 , and the same as these preferred embodiments, respectively.

[0052] [ka]

[0053] R in general formula (14) 1 and R 2 , and these preferred embodiments include R in general formula (1). 1 and R 2 , and the same as these preferred embodiments, respectively. Compound (14) can be obtained by reacting a compound represented by the following general formula (12) (compound (12)) with a compound represented by the following general formula (13) (compound (13)).

[0054] [ka]

[0055] R in general formula (12) 1 and a preferred embodiment thereof is R in general formula (1). 1 and the same as in the preferred embodiment thereof. In general formula (12), R a R represents an alkyl group. a The group is preferably a methyl group or an ethyl group.

[0056] [ka]

[0057] R in general formula (13) 2 R in general formula (1) 2 It is the same as R in general formula (13). 2 The preferred embodiment is the same as that of general formula (1).

[0058] The conditions for reacting compound (11) and compound (14) are not particularly limited. The reaction is usually carried out in a solvent in the presence of a coupling agent, or in the coupling agent without a solvent. The coupling agent is not particularly limited and examples include phosphorus oxychloride, acetic anhydride, sulfuric acid, polyphosphate, methanesulfonic acid, trifluoroacetic anhydride, etc. The solvent can be any solvent that is inert to the reaction, and is not particularly limited. Examples include toluene, xylene, and tetrahydrofuran. The reaction temperature can be room temperature to 150°C, preferably 20 to 120°C. The reaction time can be 0.1 to 48 hours, preferably 0.1 to 40 hours, and more preferably 0.1 to 24 hours. In addition, depending on the progress of the reaction, a condensing agent and / or compound (11) or compound (14) may be added to the system during the reaction.

[0059] The conditions for reacting compound (12) and compound (13) are not particularly limited. The reaction is usually carried out in a solvent in the presence of an acid or a base. The acid and base are not particularly limited and include, for example, p-toluenesulfonic acid, hydrochloric acid, acetic acid, sodium hydroxide, potassium hydroxide, etc. The solvent can be any solvent that is inert to the reaction and is not particularly limited. In addition to solvents that can be used for the reaction of compound (11) and compound (14) described above, methanol, ethanol, propanol, butanol, pentanol, hexanol, acetone, dimethylformamide, N-methylmorpholine, dimethyl sulfoxide, dimethylacetamide, pyridine, etc. can also be used. The reaction temperature can be room temperature to 120°C, with 50 to 90°C being preferred. The reaction time can be 0.5 to 72 hours, with 1 to 60 hours being preferred. Furthermore, the progress of the reaction can be checked, and an acid or base and / or compound (12) or compound (13) may be added to the system during the reaction as appropriate. The reaction of compound (12) and compound (13) can be carried out, for example, by the method described in Journal of Organic Chemistry 1958, 23, 119.

[0060] 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.

[0061] The compounds of the present invention have an absorption maximum wavelength (λmax) around 400 nm in their absorption spectrum from 400 to 800 nm. Therefore, they can efficiently absorb light around 400 nm. In this specification, the absorption maximum wavelength (λmax) refers to the absorption maximum wavelength in the absorption spectrum from 400 to 800 nm. The compounds of the present invention preferably have an absorption maximum wavelength of 400 to 440 nm, more preferably 405 to 435 nm, and even more preferably 410 to 433 nm. The absorption maximum wavelength of the compound of the present invention can be determined as the wavelength of the absorption maximum peak obtained by measuring the absorption spectrum of a chloroform solution of the compound in the 400-800 nm range using an ultraviolet-visible spectrophotometer.

[0062] The compounds of the present invention preferably have an absorbance of 0.2 or less, more preferably 0.1 or less, and even more preferably less than 0.1, at 500 nm, when the absorbance at the absorption maximum wavelength is set to 1 when the absorption spectrum of a chloroform solution is measured in the range of 400 to 800 nm. Such compounds can efficiently absorb light around 400 nm while effectively reducing the absorption of light at a wavelength of 500 nm. Such compounds can transmit green light at 500 nm while efficiently cutting out purple to blue-violet light around 400 nm, thereby reducing unwanted coloration such as redness. When such compounds are used, for example, in optical filters for image display devices, they can efficiently absorb purple to blue-violet light and improve the color purity of the light transmitted through the color filter. The compounds of the present invention may have an absorbance of 0 or greater, and may be greater than 0, at 500 nm, when the absorbance at the absorption maximum wavelength is set to 1 when the absorption spectrum of a chloroform solution is measured in the range of 400 to 800 nm.

[0063] The compounds of the present invention can efficiently absorb light at wavelengths around 400 nm. Therefore, the compounds of the present invention are suitable for applications such as optical filters. The compounds of the present invention can also be used as ultraviolet absorbers. The compounds of the present invention may be used individually or in combination of two or more. The compounds of the present invention can be used as dye compounds. The compounds of the present invention are also suitably used as dyes for optical filters such as color filters, color conversion filters, blue light cut filters, and light absorption filters.

[0064] The compounds of the present invention are preferably compounds that dissolve in organic solvents. 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. The compounds of the present invention are preferably soluble in at least one of the above organic solvents at a concentration of 0.1% by weight or more. For example, they are preferably soluble at a concentration of 0.1% to 50% by weight, more preferably at a concentration of 1% to 40% by weight, and even more preferably at a concentration of 3% to 30% by weight. More preferably, the solubility in organic solvents at 20°C is within this range. Such solubility in organic solvents is preferable because it provides good manufacturability when the compounds of the present invention are used, for example, in the manufacture of optical filters.

[0065] The compound of the present invention can be used to form a resin composition, for example, by mixing it with a resin. The above resins are not particularly limited, and thermoplastic resins, photocurable resins, thermosetting resins, etc., may be appropriately selected depending on the application of the resin 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.

[0066] The amount of the compound of the present invention in the resin composition is preferably 0.001 to 50% by weight, and more preferably 0.01 to 40% by weight, relative to the total solid content of the resin composition.

[0067] The resin composition may contain optional components other than the compound of the present invention and the resin, depending on its intended use. Examples of optional components include antioxidants, defoamers, dyes (dyes, pigments, etc.), infrared absorbers, polymerizable monomers, polymerization initiators, and sensitizers. It may also contain ultraviolet absorbers other than the compound of the present invention. The method for producing the resin composition is not particularly limited; for example, the compound and resin of the present invention, along with any optional components that may be added, may be mixed.

[0068] The compounds of the present invention and resin compositions containing them are suitably used, for example, in the manufacture of optical filters, ultraviolet absorbers, and the like. The optical filters, ultraviolet absorbers, and the like only need to contain the compounds of the present invention, and their composition is not particularly limited. An optical filter containing the compounds of the present invention is also one example of the present invention. Optical filters are not particularly limited and include, for example, lenses such as eyeglass lenses, color filters, color conversion filters, light absorption filters, and ultraviolet shielding filters. Eyeglasses include sunglasses and sports goggles. Optical filters can be suitably used as, for example, ultraviolet shielding filters, color filters, color conversion filters, and light absorption filters in eyeglasses (including sunglasses and goggles), display devices (e.g., liquid crystal displays, organic EL displays), imaging devices, lighting equipment, window glass, and other materials for insect repellent purposes (suppressing the arrival of phototactic flying insects).

[0069] The optical filter may contain the compound of the present invention and, for example, may have a support, similar to conventional filters, and may optionally have various functional layers such as an adhesive layer, an optical functional layer, an anti-reflective layer, or a hard coat layer. In the optical filter, the compound of the present invention may be contained in either the support or the various functional layers, and it is preferable, for example, that it is contained in either the support or the optical functional layer. Furthermore, the size and shape of the optical filter are not particularly limited and may be appropriately selected according to the application, etc.

[0070] The composition of the support and various functional layers 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(para-phenylene) resins, polyamide-imide resins, polyethylene naphthalate (PEN) resins, fluorinated aromatic polymer resins, (modified) acrylic resins, epoxy resins, and the like.

[0071] The method for manufacturing an 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 and a binder resin, etc., are dissolved or dispersed in a solvent, and then a coating film is formed 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, and organic solvents, etc., can be used.

[0072] Furthermore, as a method for producing an optical functional layer or support containing the compound of the present invention, the compound of the present invention can 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 can be formed by light irradiation and / or heat treatment, which can then be used as an optical functional layer or support.

[0073] As a method for manufacturing a lens, which is an example of an optical filter, various methods can be employed, such as kneading the compound of the present invention into a transparent resin and molding it by injection molding, compression molding, extrusion molding, etc., or forming an optical functional layer containing the compound of the present invention on the above-mentioned support.

[0074] This specification also discloses compounds represented by the following general formula (4). The compound represented by the following general formula (4) will be referred to as compound (4) below. Compound (4) is an example of a compound represented by the above general formula (14). Compound (4) can be used, for example, to produce compound (1) above.

[0075] [ka]

[0076] (In general formula (4), R 1 This represents a halogenated alkyl group which may have substituents, R 11b , R 12b , R 13b , R 14b , R15b , R 16b and R 17b These are, independently, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and a -COR group. 101b ,-COOR 102b ,-CONR 103b R 104b , represents an alkyl group which may have a substituent or an aryl group which may have a substituent, R 101b , R 102b , R 103b and R 104b Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group.

[0077] In the above general formula (4), R 1 A preferred embodiment is R in the general formula (1) described above. 1 This is the same as the preferred embodiment of R. 1 The group is preferably an alkyl fluoride, more preferably a trifluoromethyl group or a pentafluoroethyl group, and even more preferably a trifluoromethyl group.

[0078] In general formula (4), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b Each of these preferably independently represents a hydrogen atom, a halogen atom, or an alkyl group which may have substituents, and more preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms which may have substituents. The halogen atom is preferably a fluorine atom. R 11b ~R 17b In this, the alkyl group which may have substituents is preferably an alkyl group which may be substituted with a halogen atom, more preferably an alkyl group having 1 to 3 carbon atoms which may be substituted with a halogen atom, even more preferably an alkyl group having 1 to 3 carbon atoms which may be substituted with a fluorine atom, a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group is particularly preferred, and a trifluoromethyl group is most preferred. In general formula (4), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b Preferably, at least one of these is a fluorine atom or a group containing a fluorine atom. As a group containing a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms is preferred, and more preferred than a trifluoromethyl group. 101b , R 102b , R 103b and R 104b Each of these is preferably an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms.

[0079] All academic and patent documents cited herein are incorporated herein by reference. [Examples]

[0080] The following are examples illustrating the present invention in more detail, but the present invention is not limited to these examples.

[0081] The instruments used to measure the physical properties of the obtained compounds are as follows: (LC / MS) Shimadzu Corporation High Performance Liquid Chromatograph Mass Spectrometer LCMS-2010EV (ESI method) (GC / MS) Shimadzu Corporation Gas Chromatograph Mass Spectrometer GCMS-QP2010Plus (EI Method) (NMR) Nuclear magnetic resonance device JNM-ECZ400S manufactured by JEOL Ltd.

[0082] <Synthesis Example 1> Synthesis of compound (14-1) The compound represented by the following formula (14-1) (compound (14-1)) was synthesized by the method described in Journal of Organic Chemistry 1958, 23, 119. GC / MS:m / z=228[M] +

[0083] [ka]

[0084] <Synthesis Example 2> Synthesis of compound (14-2) Compound (14-2) represented by the following formula (14-2) was synthesized using the same method as in the synthesis of compound (14-1). GC / MS:m / z=318[M] +

[0085] [ka]

[0086] <Synthesis Example 3> Synthesis of compound (14-3) Compound (14-3) represented by the following formula (14-3) was synthesized using the same method as in the synthesis of compound (14-1). GC / MS:m / z=246[M] +

[0087] [ka]

[0088] <Synthesis Example 4> Synthesis of compound (14-4) Compound (14-4) represented by the following formula (14-4) was synthesized using the same method as in the synthesis of compound (14-1). GC / MS:m / z=368[M] +

[0089] [ka]

[0090] <Synthesis Example 5> Synthesis of compound (14-5) The compound represented by the following formula (14-5) (compound (14-5)) was synthesized using the method described below. GC / MS:m / z=404[M] +

[0091] [ka]

[0092] In a four-necked flask equipped with a thermometer and condenser, 3.3 g of octafluoronaphthalene and 15 mL of ethanol were charged. At 40°C, 1.8 g of hydrazine monohydrate was added dropwise, and the mixture was stirred for 4 hours. After the reaction was complete, the mixture was allowed to cool. The solution was drained into water, the precipitate was filtered off, washed with water, and dried to obtain 3.5 g of 1,2,3,4,5,6,8-heptafluoro-7-hydrazinonaphthalene. In a four-necked flask equipped with a thermometer and condenser, 3.1 g of 1,2,3,4,5,6,8-heptafluoro-7-hydrazinonaphthalene, 0.2 g of p-toluenesulfonic acid monohydrate, 16 mL of ethanol, and 2 g of ethyl trifluoroacetoethyl acetate were charged and stirred at 70°C for 24 hours. Then, 0.2 g of p-toluenesulfonic acid monohydrate was added and stirred for 6.5 hours. Finally, 0.2 g of p-toluenesulfonic acid monohydrate and 1 g of ethyl trifluoroacetoethyl acetate were added and stirred for 16 hours. After cooling, the mixture was drained into water, the precipitate was filtered off, washed with hexane, and dried to obtain 3 g of compound (14-5).

[0093] <Example 1> Synthesis of compound (1-1) The compound represented by the following formula (1-1) (compound (1-1)) was synthesized using the method described below. LC / MS: m / z = 425[M+H] +

[0094] [ka]

[0095] In a four-necked flask equipped with a thermometer and condenser, 2.2 g of 2,6-dimethyl-γ-pyrone, 5.7 g of compound (14-2), and 45 mL of toluene were charged. 3.3 g of phosphorus oxychloride was added dropwise at 100°C and the mixture was stirred for 2 hours. After the reaction was complete, the mixture was allowed to cool, drained into water / toluene, and neutralized. The mixture was extracted with toluene, the solvent was removed by distillation, and the solution was recrystallized with ethyl acetate and hexane. The resulting mixture was then removed and dried to obtain 2.9 g of compound (1-1).

[0096] <Example 2> Synthesis of compounds (1-2) The compound represented by the following formula (1-2) (compound (1-2)) was synthesized using the method described below. LC / MS: m / z = 335[M+H] +

[0097] [ka]

[0098] In a four-necked flask equipped with a thermometer and condenser, 4.8 g of 2,6-dimethyl-γ-pyrone, 6.0 g of compound (14-1), and 26 mL of acetic anhydride were charged and stirred at 100°C for 40 hours. After the reaction was complete, the mixture was allowed to cool, drained into water / ethyl acetate, and neutralized. The solid obtained by extracting with ethyl acetate and removing the solvent was washed with isopropyl alcohol (IPA) and dried to obtain 1.2 g of compound (1-2).

[0099] <Example 3> Synthesis of compounds (1-3) Compound (1-3) was obtained in the same manner as in the synthesis of compound (1-1) of Example 1, except that compound (14-2) was replaced with compound (14-3). LC / MS: m / z = 353[M+H] +

[0100] [ka]

[0101] <Example 4> Synthesis of compounds (1-4) Compound (1-4) was obtained by the same procedure as in the synthesis of compound (1-1) of Example 1, except that compound (14-2) was replaced with compound (14-4). LC / MS: m / z = 475[M+H] +

[0102] [ka]

[0103] The compounds (1-1) to (1-4) obtained in Examples 1 to 4 are represented by the following general formula (1B), where R 11 ~R 15 These are compounds in which each of the atoms or groups shown in Table 1 below is present.

[0104] [ka]

[0105] [Table 1]

[0106] <Example 5> Synthesis of compounds (1-5) The compound represented by the following formula (1-5) (compound (1-5)) was synthesized using the method described below.

[0107] [ka]

[0108] In a four-necked flask equipped with a thermometer and condenser, 1.5 g of 2,6-dimethylpyrone, 5 g of compound (14-5), and 35 mL of toluene were charged and heated to 100°C. 2.3 g of phosphorus oxychloride was added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. After the reaction was complete, the mixture was allowed to cool and then drained into water / toluene for neutralization. The solid obtained by extraction with toluene and subsequent removal of the solvent was washed with the solvent to obtain 2.1 g of compound (1-5). LC / MS: m / z = 511[M+H] +

[0109] <Comparative Example 1> The compound represented by the following formula (15) (CAS RN: 93331-50-1) was synthesized according to the method described in Non-Patent Literature 2 (Non-Patent Literature 2: Helvetica Chimica Acta. 1962, 45, pp1908-1917).

[0110] [ka]

[0111] The compounds obtained above were evaluated as follows. <Spectroscopic Characteristics Test> For each compound obtained in the examples and comparative examples, the absorption spectrum was measured in chloroform, and the absorption maximum wavelength (λmax) in the 400-800 nm range was determined. The absorbance (A) at this absorption maximum wavelength was calculated. λmax When (A) is set to 1, the absorbance at a wavelength of 500 nm (A 500nm ) relative value (A 500nm / A λmax ) was sought. The measurement instrument used was the V-560 UV-Vis spectrophotometer manufactured by JASCO Corporation.

[0112] Absorbance at a wavelength of 500 nm (A 500nm ) relative value (A 500nm / A λmax The following criteria were used for evaluation. Absorbance at a wavelength of 500 nm (A 500nm ) relative value (A 500nm / A λmax ) Evaluation Criteria A: Relative value (A 500nm / A λmax ) is less than 0.1 B: Relative value (A 500nm / A λmax ) is 0.1 or greater, and less than 0.2 C: Relative value (A 500nm / A λmax ) is 0.2 or higher Absorption maximum wavelength (λmax) and absorbance at 500 nm (A) of the compounds in the examples and comparative examples. 500nm ) relative value (A 500nm / A λmax The evaluation results are shown in Table 2.

[0113] [Table 2]

[0114] <Lightfastness Test> Lightfastness tests were performed on each compound obtained in Examples 1-4 and Comparative Example 1. A thin film with a thickness of 1.5 μm was prepared by dissolving 10 mg of the compound in 5 mL of an 8 wt% polymethacrylate toluene solution, coating it onto a glass substrate by spin coating, and drying it. The fabricated thin film was continuously irradiated with light from a xenon lamp (142 klux) for 96 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 determined according to the following calculation formula (I). Compound retention rate (%) = {(1-T1) / (1-T0)} × 100 (I) [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. A: Compound retention rate of 85% or more B: Compound retention rate is 70% or more, but less than 85%. C: Compound retention rate is less than 70%

[0115] The results of the lightfastness test are shown in Table 3.

[0116] [Table 3]

[0117] From the results above, the compound in the example had a lower relative absorbance at a wavelength of 500 nm compared to Comparative Example 1. Furthermore, the compound in the example exhibited good light resistance. The compound in Comparative Example 1 also had an absorption peak around 350 nm, and the absorbance of this peak was greater than that of the peak with a maximum at 426 nm.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 (In general formula (1), R １ This represents a halogenated alkyl group which may have substituents, R ２ This represents an aryl group which may have substituents, R ２１ , R ２２ , R ２３ and R ２４ Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxycarbonyl group, or an optionally substituted alkylcarbonyl group.

2. R in the general formula (1) １ The compound according to claim 1, wherein is an alkyl fluoride.

3. R in the general formula (1) ２ The compound according to claim 1 or 2, wherein is a group represented by the following general formula (2) or (3). 【Chemistry 2】 (In general formula (2), R １１ａ , R １２ａ , R １３ａ , R １４ａ and R １５ａ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -COR １０１ａ , -COOR １０２ａ , -CONR １０３ａ R １０４ａ , an alkyl group which may have a substituent or an aryl group which may have a substituent, R １０１ａ , R １０２ａ , R １０３ａ and R １０４ａ Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates the bonding site with general formula (1). 【Transformation 3】 (In general formula (3), R １１ｂ , R １２ｂ , R １３ｂ , R １４ｂ , R １５ｂ , R １６ｂ and R １７ｂ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -COR. １０１ｂ , -COOR １０２ｂ , -CONR １０３ｂ R １０４ｂ , represents an alkyl group which may have substituents or an aryl group which may have substituents, R １０１ｂ , R １０２ｂ , R １０３ｂ and R １０４ｂ Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates the bonding site with general formula (1).

4. In the above general formula (2), R １１ａ , R １２ａ , R １３ａ , R １４ａ and R １５ａ The compound according to claim 3, wherein each represents independently a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent.

5. R in the general formula (3) １１ｂ , R １２ｂ , R １３ｂ , R １４ｂ , R １５ｂ , R １６ｂ and R １７ｂ The compound according to claim 3, wherein each represents independently a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent.

6. R in the general formula (1) ２１ , R ２２ , R ２３ and R ２４ The compound according to claim 1 or 2, wherein each represents independently a hydrogen atom or an alkyl group which may have substituents.

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

8. A compound represented by the following general formula (4). 【Chemistry 4】 (In general formula (4), R １ This represents a halogenated alkyl group which may have substituents, R １１ｂ , R １２ｂ , R １３ｂ , R １４ｂ , R １５ｂ , R １６ｂ and R １７ｂ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -COR. １０１ｂ , -COOR １０２ｂ , -CONR １０３ｂ R １０４ｂ , represents an alkyl group which may have substituents or an aryl group which may have substituents, R １０１ｂ , R １０２ｂ , R １０３ｂ and R １０４ｂ Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group.

9. R in the general formula (4) １１ｂ , R １２ｂ , R １３ｂ , R １４ｂ , R １５ｂ , R １６ｂ and R １７ｂ The compound according to claim 8, wherein at least one of them is a fluorine atom or a group containing a fluorine atom.

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