Compounds and optical filters

Abstract

To provide a compound that has excellent heat resistance, an absorption maximum wavelength near the wavelength 400nm, and also has a sharp absorption spectrum.SOLUTION: Provided is a compound expressed by the following general 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, and R25 denotes an alkyl group which may have a hydrogen atom and a substituent, a heterocyclic group or the like 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 pyrazolone derivatives 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 project] [Problems that the invention aims to solve]

[0005] Optical filters and various instruments and devices using them are sometimes used in high-temperature environments. Furthermore, the manufacture of optical filters may involve high-temperature mixing and heat treatment. Therefore, compounds with good heat resistance that can absorb light of specific wavelengths are desired. In recent years, there has also been a demand for optical filters that cut out a narrow range of light wavelengths. For such purposes, compounds with sharp absorption spectra are required. The pyrazolone derivatives described in Non-Patent Documents 1 and 2 are compounds that can be used for optical filter applications. However, for example, the pyrazolone derivative described in Non-Patent Document 1, while having good heat resistance, had a broad peak in its absorption spectrum, with a gently spreading portion (referred to as the "tail portion" in this specification) from the peak showing the absorption maximum at the longer wavelength side of the absorption maximum to the baseline. When such a tail portion is in the visible light region, even if the shape of the peak showing the absorption maximum wavelength (the shape of the tip) is sharp, it is difficult to say that it has a sharp absorption spectrum including the wavelengths before and after the absorption maximum wavelength.

[0006] The present invention aims to provide a compound that has good heat resistance, an absorption maximum wavelength around 400 nm, and a sharp absorption spectrum. [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) has good heat resistance, an absorption maximum wavelength around 400 nm, and a sharp absorption spectrum including the tail portion. 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 represents a halogenated alkyl group which may have a substituent, R 2 represents an aryl group which may have a substituent, R 21 , R 22 , R 23 and R 24 each independently represent 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, R 25 represents a hydrogen atom, an alkyl group which may have a substituent, a heterocyclic group which may have a substituent or a group represented by the following general formula (2).

[0011]

Chemical Formula

[0012] (In general formula (2), R 31 , R 32 , R 33 , R 34 and R 35 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -COR 201 , -COOR 202 , -CONR 203 R 204 , an alkyl group which may have a substituent, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, -OR 205 , -SR 206 or -NR 207 R 208 represents, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 and R 208Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates a bonding site with general formula (1). <2> R in the above general formula (1) 1 The above is an alkyl fluoride. <1> The compounds described above. <3> R in the above general formula (1) 2 The above is a group represented by the following general formula (3) or (4). <1> or <2> The compounds described above.

[0013] [ka]

[0014] (In general formula (3), R 11a , R 12a , R 13a , R 14a and R 15a These are, independently, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and a -COR group. 101a ,-COOR 102a ,-CONR 103a R 104a , represents an alkyl group which may have substituents or an aryl group which may have substituents, 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).

[0015] [ka]

[0016] (In general formula (4), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17bThese 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). <4> In the above general formula (3), 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, and R in the above general formula (4) 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. <5> R in the above general formula (1) 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> ~ <4> A compound described in any of the following. <6> R in the above general formula (1) 25 This represents an alkyl group which may have substituents or a group represented by the above general formula (2), <1> ~ <5> A compound described in any of the following. <7> In the above general formula (2), R 31 , R 32 , R 33 , R 34 and R 35 These are, independently, a hydrogen atom, a halogen atom, and -OR 205R represents an alkyl group which may have substituents. 205 The above represents an alkyl group which may have substituents. <1> ~ <6> A compound described in any of the following. <8> the above <1> ~ <7> An optical filter characterized by containing any of the compounds described in one of the following. [Effects of the Invention]

[0017] According to the present invention, it is possible to provide a compound that has good heat resistance, has an absorption maximum wavelength around 400 nm, and has a sharp absorption spectrum. [Modes for carrying out the invention]

[0018] 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).

[0019] [ka]

[0020] (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. R 25 This represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted heterocyclic group, or a group represented by the following general formula (2).

[0021] [ka]

[0022] (In general formula (2), R 31 , R 32 , R 33 , R 34 and R 35 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -COR 201 , -COOR 202 , -CONR 203 R 204 , an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclic group, -OR 205 , -SR 206 or -NR 207 R 208 , R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 and R 208 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group. * indicates a bonding site to general formula (1).))

[0023] In the present invention, the optionally substituted halogenated alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, and still more preferably 1 to 2 carbon atoms. In the present specification, the number of carbon atoms of an optionally substituted group refers to the total number of carbon atoms of the entire group including the substituent(s). In the present invention, the alkyl group may be linear, branched or cyclic. Preferred examples of the optionally substituted halogenated alkyl group include groups in which part or all of hydrogen atoms in an alkyl group having 1 to 6 carbon atoms are substituted with halogen atoms. The optionally substituted halogenated alkyl group is preferably a linear halogenated alkyl group, and more preferably a linear halogenated alkyl group having 1 to 3 carbon atoms. Examples of the halogen in the halogenated alkyl group include fluorine, chlorine and bromine, with fluorine being preferred.

[0024] In general formula (1), R 1 It 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] Examples of heterocyclic groups that may have substituents include heterocyclic groups having 2 to 8 carbon atoms that may have substituents. Examples of heterocyclic groups include nitrogen-containing heterocyclic rings such as pyrrole rings, pyridine rings, quinoline rings, pyrimidine rings, pyridazine rings, pyrazine rings, imidazole rings, benzimidazole rings, triazine rings, triazole rings, tetrazole rings, pyrrolidine rings, and piperidine rings; oxygen-containing heterocyclic rings such as furan rings, benzofuran rings, and dioxane rings; sulfur-containing heterocyclic rings such as thiophene rings and benzothiophene rings; heterocyclic rings containing oxygen and nitrogen atoms such as oxazole rings and benzoxazole rings; and sulfur-containing heterocyclic rings such as thiazole rings, benzothiazole rings, and thiadiazole rings. These rings may further form fused rings with other carbon rings (e.g., benzene rings) or heterocyclic rings (e.g., pyridine rings). Preferred heterocyclic groups include pyridine rings, thiophene rings, tetrazole rings, thiazole rings, imidazole rings, benzimidazole rings, triazole rings, pyrrole rings, oxadiazole rings, pyrazole rings, piperidine rings, furan rings, oxazole rings, and pyrrolidine rings. The substituents in the heterocyclic group, which may have substituents, are not particularly limited. Examples include halogen atoms, alkyl groups, and aryl groups.

[0033] In general formula (1), R 21 , R 22 , R 23 and R 24 Each of these preferably independently represents a hydrogen atom or an optionally substituted alkyl group, more preferably a hydrogen atom or an optionally substituted C1-C3 alkyl group, even more preferably a hydrogen atom or a C1-C3 alkyl group, and particularly preferably a hydrogen atom, a methyl group, or an ethyl group. In one embodiment, R 21 and R 24 Each of these preferably independently represents an alkyl group which may have substituents, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group or an ethyl group. 21 and R 24 It is particularly preferable that R represents a methyl group. In one embodiment, 22and R 23 It is preferable that this represents a hydrogen atom.

[0034] In the above general formula (1), R 25 R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted heterocyclic group, or a group represented by the above general formula (2). 25 In this context, a methylpyridino group is preferred as the heterocyclic group which may have substituents. R 25 Preferably, is an alkyl group which may have substituents or a group represented by the above general formula (2). 25 The optionally substituted alkyl group in is preferably an optionally substituted C1-C8 alkyl group, more preferably an optionally substituted C1-C8 linear alkyl group, even more preferably an optionally substituted methyl group, particularly preferably a methyl group, ethyl group, propyl group, butyl group, or benzyl group, and most preferably a methyl group or benzyl group.

[0035] The above R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 and R 208 Each of these preferably independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have substituents, or an aryl group having 6 to 20 carbon atoms which may have substituents. 31 , R 32 , R 33 , R 34 and R 35 These are, independently, a hydrogen atom, a halogen atom, and -OR 205 Alternatively, it is preferable to represent an alkyl group which may have substituents, a hydrogen atom, -OR 205 Or, more preferably, it represents an alkyl group which may have substituents. 205It is preferable that it represents an alkyl group which may have substituents, more preferably an alkyl group having 1 to 3 carbon atoms which may have substituents, even more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.

[0036] R 31 ~R 35 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 methyl group or a trifluoromethyl group is most preferred.

[0037] In the above general formula (1), R 2 R represents an aryl group which may have substituents. 2 As the aryl group which may have substituents, the group represented by the following general formula (3) and the group represented by the following general formula (4) are preferred. 2 Preferably, the group is represented by the following general formula (3) or (4).

[0038] [ka]

[0039] (In general formula (3), R 11a , R 12a , R 13a , R 14a and R 15a These are, independently, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and a -COR group. 101a ,-COOR 102a ,-CONR 103a R 104a , represents an alkyl group which may have substituents or an aryl group which may have substituents, R 101a , R 102a , R 103a and R 104aEach of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates a bonding site with general formula (1).

[0040] [ka]

[0041] (In general formula (4), 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 a bonding site with general formula (1).

[0042] 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.

[0043] In general formula (3), R 11a , R 12a , R 13a , R 14a and R 15aEach of these elements independently preferably represents a hydrogen atom, a halogen atom, or an alkyl group which may have substituents; more preferably a hydrogen atom or a halogen atom; even more preferably a hydrogen atom or a fluorine atom; and particularly preferably a fluorine atom.

[0044] In general formula (4), R 11b , R 12b , R 13b , R 14b , R 15b , R 16b and R 17b Each of these elements independently preferably represents a hydrogen atom, a halogen atom, or an alkyl group which may have substituents; more preferably a hydrogen atom or a halogen atom; even more preferably a hydrogen atom or a fluorine atom; and particularly preferably a fluorine atom.

[0045] R 11a ~R 15a and 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 methyl group or a trifluoromethyl group is most preferred.

[0046] Examples of preferred embodiments of compound (1) include, for example, the compound represented by formula (1-1), formula (1-2), formula (1-3), formula (1-4), formula (1-5), formula (1-6), formula (1-7), formula (1-8), formula (1-9), and formula (1-10), as described below.

[0047] 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.

[0048] 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.

[0049] 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 (15) (compound (15)) with a compound represented by the following general formula (16) (compound (16)).

[0050] [ka]

[0051] 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 23It is a compound in which the atom is a hydrogen atom.

[0052] [ka]

[0053] R in general formula (15) 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 (15) 1 , R 2 , R 21 and R 24 The preferred embodiment is the same as that of general formula (1).

[0054] [ka]

[0055] R in general formula (16) 25 and a preferred embodiment thereof is R in general formula (1). 25 And the same as the preferred embodiment thereof.

[0056] The above compound (15) can be obtained, for example, 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)).

[0057] [ka]

[0058] R in general formula (11) 21 and R 24 , and these preferred embodiments include R in general formula (1). 21 and R 24 , as well as the same as these preferred embodiments.

[0059] [ka]

[0060] R in general formula (14) 1 and R 2 , and these preferred embodiments include R in general formula (1). 1 and R 2 , as well as the same as these preferred embodiments.

[0061] 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)).

[0062] [ka]

[0063] 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.

[0064] [ka]

[0065] 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).

[0066] The conditions under which compounds (15) and (16) react are not particularly limited. The reaction is usually carried out in a solvent. The reaction may also be carried out in the presence of a base. The base is not particularly limited, and examples include triethylamine. 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, toluene, xylene, dimethylformamide, N-methylmorpholine, dimethyl sulfoxide, dimethylacetamide, pyridine, tetrahydrofuran, and chloroform. The reaction temperature can be room temperature to 110°C, with 40 to 85°C being preferred. The reaction time can be 0.5 to 72 hours, with 0.5 to 24 hours being preferred.

[0067] 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, and is preferably 20 to 120°C. The reaction time can be 0.1 to 48 hours, is 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 as appropriate.

[0068] 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 or base is not particularly limited and examples include p-toluenesulfonic acid, hydrochloric acid, acetic acid, sodium hydroxide, potassium hydroxide, etc. The solvent may be any solvent that is inert to the reaction and is not particularly limited. Solvents that can be used for the reaction of compound (15) and compound (16) above can be used. The reaction temperature can be room temperature to 120°C, and is preferably 50 to 90°C. The reaction time can be 0.5 to 72 hours, and is preferably 1 to 60 hours. In addition, the progress of the reaction may be checked and an acid or base may be added to the system during the reaction as appropriate. Compound (12) or compound (13) may also be added to the system during the reaction. 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.

[0069] 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.

[0070] The compounds of the present invention have an absorption maximum wavelength (λmax) around 400 nm. Therefore, they can efficiently absorb light around 400 nm. The absorption maximum wavelength of the compounds of the present invention is preferably 390 to 420 nm, more preferably 395 to 416 nm, and even more preferably 400 to 415 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 with an ultraviolet-visible spectrophotometer.

[0071] The compounds of the present invention typically have a sharp absorption spectrum, including the tail portion. As an indicator of having a sharp absorption spectrum, including the tail portion, it is preferable that the wavelength width from the baseline rise wavelength on the longer wavelength side of the absorption maximum wavelength to the absorption maximum wavelength in the absorption spectrum is 80 nm or less. Furthermore, it is preferable that the compounds of the present invention have a full width at half maximum at the absorption maximum wavelength of 30 nm or less. In this specification, the baseline rise wavelength is defined as the wavelength at which the absorbance viewed from the longer wavelength side is 0.01 or greater, when the absorbance at the absorption maximum wavelength is set to 1. Then, the distance (wavelength width) from the rising wavelength to the absorption maximum wavelength is determined. In this specification, the full width at half maximum (FWHM) is a numerical value that indicates the steepness of the absorption spectrum, as expressed by the following formula. Half-width = λ 1 / 2 -λ max In the above formula, λ max λ represents the absorption maximum wavelength in a chloroform solution at 390-800 nm. 1 / 2 The absorbance at that wavelength is λ max The absorbance at is 1 / 2, and λ 1 / 2 >λ max It represents the wavelength. The smaller the full width at half maximum (FMAX) as described above, the steeper the absorption spectrum becomes at longer wavelengths beyond the absorption maximum. The compound of the present invention more preferably has a full width at half maximum (FWHM) of 28 nm or less, and even more preferably 27 nm or less. The FWHM may be, for example, 10 nm or more. The above full width at half maximum can be determined, for example, from the absorption maximum peak obtained by measuring the absorption spectrum of a chloroform solution of the above compound using a UV-Vis spectrophotometer. Compounds having the absorption spectra described above are particularly suitable for use in optical filters and the like because they possess sharp absorption spectra. Furthermore, the aforementioned base portion can be interpreted by referring to the base portion described in International Publication No. 2019 / 131473.

[0072] The compounds of the present invention have good heat resistance, an absorption maximum wavelength around 400 nm, and a sharp absorption spectrum. The compounds of the present invention can efficiently absorb light around 400 nm. Therefore, the compounds of the present invention are suitable for applications such as optical filters. In one embodiment, 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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).

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] All academic and patent documents cited herein are incorporated herein by reference. [Examples]

[0084] The following are examples illustrating the present invention in more detail, but the present invention is not limited to these examples.

[0085] 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.

[0086] <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] +

[0087] [ka]

[0088] <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] +

[0089] [ka]

[0090] <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] +

[0091] [ka]

[0092] <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] +

[0093] [ka]

[0094] <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] +

[0095] [ka]

[0096] 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).

[0097] <Synthesis Example 6> Synthesis of compound (15-1) The compound represented by the following formula (15-1) (compound (15-1)) was synthesized using the method described below. LC / MS: m / z = 425[M+H] +

[0098] [ka]

[0099] 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 compound (15-1) was recrystallized with ethyl acetate and hexane, then removed and dried to obtain 2.9 g of compound (15-1).

[0100] <Synthesis Example 7> Synthesis of compound (15-2) The compound represented by the following formula (15-2) (compound (15-2)) was synthesized using the method described below. LC / MS: m / z = 335[M+H] +

[0101] [ka]

[0102] 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 (15-2).

[0103] <Synthesis Example 8> Synthesis of compound (15-3) Compound (15-3) was synthesized in the same manner as in the synthesis of compound (15-1) in Synthesis Example 6, except that compound (14-2) was replaced with compound (14-3). LC / MS: m / z = 353[M+H] +

[0104] [ka]

[0105] <Synthesis Example 9> Synthesis of compound (15-4) Compound (15-4) was synthesized in the same manner as in the synthesis of compound (15-1) in Synthesis Example 6, except that compound (14-2) was replaced with compound (14-4). LC / MS: m / z = 475[M+H] +

[0106] [ka]

[0107] <Synthesis Example 10> Synthesis of compound (15-5) The compound represented by the following formula (15-5) (compound (15-5)) was synthesized using the method described below.

[0108] [ka]

[0109] 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 (15-5). LC / MS: m / z = 511[M+H]+

[0110] <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.

[0111] [ka]

[0112] In a four-necked flask equipped with a thermometer and condenser, 0.76 g of compound (15-1), 40 mL of chloroform, and 1.5 g of 40% methylamine aqueous solution were charged and stirred at 55°C for 2 hours. After the reaction was complete, the mixture was allowed to cool, drained into water / chloroform, and extracted with chloroform to remove the solvent. The resulting solid was washed with hexane and dried to obtain 0.7 g of compound (1-1). LC / MS: m / z = 438[M+H] +

[0113] <Example 2> Synthesis of compounds (1-2) Compound (1-2) was obtained in the same manner as in the synthesis of compound (1-1) of Example 1, except that compound (15-1) was replaced with compound (15-2). LC / MS: m / z = 348[M+H] +

[0114] [ka]

[0115] <Example 3> Synthesis of compounds (1-3) The compound represented by the following formula (1-3) (compound (1-3)) was synthesized using the method described below.

[0116] [ka]

[0117] Into a four-necked flask equipped with a thermometer and a cooling tube were charged 1.4 g of compound (15-1), 20 mL of ethanol, 6 drops of triethylamine, and 0.5 g of benzylamine. The mixture was stirred at 70°C for 15 hours, and allowed to cool naturally after completion of the reaction. The reaction solution was poured into water, the precipitate was collected by filtration, and the obtained solid was washed with water and dried to obtain 1.3 g of compound (1-3). LC / MS: m / z=514 [M+H] +

[0118] <Example 4> Synthesis of compound (1-4) Compound (1-4) represented by the following formula (1-4) was obtained in the same manner as in the synthesis of compound (1-3) of Example 3, except that benzylamine was replaced with aniline. LC / MS: m / z=500 [M+H] +

[0119]

Chemical formula

[0120] <Example 5> Synthesis of compound (1-5) Compound (1-5) represented by the following formula (1-5) was obtained in the same manner as in the synthesis of compound (1-3) of Example 3, except that benzylamine was replaced with 4-aminobenzotrifluoride. LC / MS: m / z=568 [M+H] +

[0121]

Chemical formula

[0122] <Example 6> Synthesis of compound (1-6) Compound (1-6) represented by the following formula (1-6) was obtained in the same manner as in the synthesis of compound (1-3) of Example 3, except that benzylamine was replaced with 2,4,6-trimethylaniline. LC / MS: m / z=542[M+H] +

[0123]

Chemical

[0124] <Example 7> Synthesis of Compound (1-7) A compound represented by the following formula (1-7) (compound (1-7)) was obtained in the same manner as in the synthesis of compound (1-3) of Example 3, except that benzylamine was replaced with p-anisidine. LC / MS: m / z=530[M+H] +

[0125]

Chemical

[0126] <Example 8> Synthesis of Compound (1-8) A compound represented by the following formula (1-8) (compound (1-8)) was obtained in the same manner as in the synthesis of compound (1-3) of Example 3, except that benzylamine was replaced with 3,5-dimethoxyaniline. LC / MS: m / z=560[M+H] +

[0127]

Chemical

[0128] Compounds (1-1) to (1-3) obtained in Examples 1 to 3 are compounds in which, in the following general formula (1B), R 11 to R 15 and R 25 are each an atom or group shown in the following Table 1. Me represents a methyl group. CH2Ph represents a benzyl group.

[0129]

Chemical

[0130]

Table 1

[0131] In compounds (1-4) to (1-8) obtained in Examples 4 to 8, in the following general formula (1C), R 11 to R 15 and R 31 to R 35 are each an atom or a group shown in the following Table 2.

[0132]

Chemical Formula

[0133]

Table 2

[0134] <Example 9> Synthesis of Compound (1-9) Into a four-necked flask equipped with a thermometer and a cooling tube, 0.76 g of compound (15-5), 14 mL of ethanol, and 1.2 g of 40% aqueous methylamine solution were charged, and the mixture was stirred at 65°C for 2 hours, and allowed to cool after the completion of the reaction. The reaction solution was poured into water / chloroform for extraction, the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography to obtain 0.3 g of the compound represented by the following formula (1-9) (compound (1-9)). LC / MS: m / z=524[M+H] +

[0135]

Chemical Formula

[0136] <Example 10> Synthesis of Compound (1-10) In the synthesis of compound (1-3) of Example 3, compound (15-1) was replaced with compound (15-5), and benzylamine was replaced with aniline, except that the procedure was the same to obtain 0.8 g of compound (compound (1-10)) represented by the following formula (1-10). LC / MS: m / z = 586[M+H] +

[0137] [ka]

[0138] <Comparative Example 1> The compound represented by the following formula (17) was synthesized in accordance with the method described in Non-Patent Document 2 (Non-Patent Document 2: Helvetica Chimica Acta. 1962, 45, pp1908-1917).

[0139] [ka]

[0140] The compounds obtained above were evaluated as follows. The results are shown in Tables 3 and 4. <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), rise wavelength, distance from the rise wavelength to the absorption maximum wavelength (wavelength width), and full width at half maximum at the absorption maximum wavelength were determined. The measurement instrument used was the V-560 UV-Vis spectrophotometer manufactured by JASCO Corporation. The rise wavelength was defined as the wavelength at which the absorbance viewed from the longer wavelength side is 0.01 or greater, when the absorbance at the absorption maximum wavelength in the range of 390 to 800 nm is set to 1. In Tables 3 and 4, "λmax - Wavelength width to rise wavelength" shows the distance (wavelength width) from the rise wavelength to the absorption maximum wavelength.

[0141] The full width at half maximum (FMAX) is a numerical value that indicates the steepness of the absorption spectrum, as shown by the following equation (I). Half-width = λ1 / 2 -λ max (I) In the above formula, λ max λ represents the absorption maximum wavelength in the 390-800 nm range. 1 / 2 The absorbance at that wavelength is λ max The absorbance at is 1 / 2, and λ 1 / 2 >λ max It represents the wavelength.

[0142] <Thermal decomposition temperature> For each compound obtained in Examples 1-8 and Comparative Example 1, the weight loss due to thermal decomposition was measured using a Shimadzu Corporation TGA-50 thermogravimetric analyzer under the following measurement conditions. The temperature at which the tangent line at the inflection point intersected with the extension of the baseline was defined as the decomposition start temperature. (Measurement conditions) The measurement was performed under the following conditions: sample volume 5 mg, heating rate 10°C / min (maximum temperature reached 400°C), nitrogen atmosphere, and flow rate 10 mL / min. Heat resistance was evaluated based on the following criteria, starting from the decomposition initiation temperature. A: Decomposition start temperature is 300°C or higher B: Decomposition start temperature is 250°C or higher, but less than 300°C. C: Decomposition start temperature is below 250°C The results are shown in Table 3.

[0143] [Table 3]

[0144] <Heat resistance test> For each compound obtained in Examples 9-10 and Comparative Example 1, thin films were prepared using the following method and heat resistance tests were performed. Ten mg of the compound was dissolved in 5 mL of a toluene-chloroform mixed solvent containing 8% by weight of polymethyl methacrylate. The mixture was then coated onto a glass substrate by spin coating and dried to produce a thin film. The fabricated thin films were left to stand in an electric furnace set to 230°C for 2 hours. The transmittance of the thin films before the test (before standing in the electric furnace) and after the test (after standing in the electric furnace for 2 hours) was measured using a spectrophotometer, and the remaining compound percentage was determined according to the following formula (II). Compound retention rate (%) = {(1-T1) / (1-T0)} × 100 (II) In formula (II) above, T0 is the transmittance before the test, and T1 is the transmittance after the test, with T0 and T1 being between 0 and 1. Note that "transmittance" refers to the transmittance at the absorption maximum wavelength of each compound, and the higher the residual rate, the less the compound is decomposed by heat, indicating higher heat resistance.

[0145] The heat resistance test results were evaluated according to the following criteria. The results are shown in Table 4. A: Compound retention rate of 80% or more B: Compound retention rate is 60% or more, but less than 80%. C: Compound retention rate is less than 60%

[0146] [Table 4]

[0147] From the above results, the compound produced in the example had an absorption maximum wavelength around 400 nm and a narrower full width at half maximum than the compound in Comparative Example 1. The compound produced in the example had a sharper absorption spectrum, including the tail portion, compared to the compound in Comparative Example 1. The compound in Comparative Example 1 also had an absorption peak around 350 nm. The compound in the example also exhibited good heat resistance.

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. R ２５ This represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted heterocyclic group, or a group represented by the following general formula (2). 【Chemistry 2】 (In general formula (2), R ３１ , R ３２ , R ３３ , R ３４ and R ３５ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -COR ２０１ , -COOR ２０２ , -CONR ２０３ R ２０４ , an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclic group, -OR ２０５ , -SR ２０６ or -NR ２０７ R ２０８ , R ２０１ , R ２０２ , R ２０３ , R ２０４ , R ２０５ , R ２０６ , R ２０７ and R ２０８ Each of these independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. * indicates a bonding site with general formula (1).

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 (3) or (4). 【Transformation 3】 (In general formula (3), R １１ａ , R １２ａ , R １３ａ , R １４ａ and R １５ａ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -COR. １０１ａ , -COOR １０２ａ , -CONR １０３ａ R １０４ａ , represents an alkyl group which may have substituents or an aryl group which may have substituents, 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). 【Chemistry 4】 (In general formula (4), 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. R in the general formula (3) １１ａ , R １２ａ , R １３ａ , R １４ａ and R １５ａ Each independently represents a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and 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 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 (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.

6. R in the general formula (1) ２５ The compound according to claim 1 or 2, wherein is an alkyl group which may have substituents or a group represented by the general formula (2).

7. In the above general formula (2), R ３１ , R ３２ , R ３３ , R ３４ and R ３５ These are, independently, a hydrogen atom, a halogen atom, and -OR ２０５ or represents an alkyl group which may have substituents, R ２０５ The compound according to claim 1 or 2, wherein is an alkyl group which may have substituents.

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

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