JP7288633B2 - Boron complex compound and optical filter - Google Patents

Description

The present invention relates to boron complex compounds and optical filters.

Optical filters are used to cut out certain wavelengths of light from light emitted from lighting devices, display devices, and the like.
Compounds capable of absorbing light of a specific wavelength are used in such optical filters.

Dipyrromethene compounds are known to form complexes with various main group elements and transition metals and have optical properties capable of absorbing light of specific wavelengths.

For example, Non-Patent Document 1 discloses a dipyrylmethene-type copper complex compound having a maximum absorption wavelength in the vicinity of a wavelength of 500 nm.

Nihon Kagaku Zasshi, Vol. 81, No. 11, p.1740-1746 (1960)

The dipyrylmethene-type copper complex compound disclosed in Non-Patent Document 1 is useful as a dye that absorbs light with a wavelength of around 500 nm, but can more selectively absorb light with a wavelength of around 500 nm, causing a decrease in contrast. There is a demand for the development of a dye compound that suppresses the resulting fluorescence and has excellent light resistance.

An object of the present invention is to provide a compound that can selectively absorb light having a wavelength of about 500 nm, suppresses fluorescence, and has excellent light resistance.

The present inventors have made intensive studies to solve the above problems, and found that a boron complex compound represented by the following general formula (1) can selectively absorb light with a wavelength of 480 to 520 nm, resulting in a decrease in contrast. The inventors have found that the fluorescence that causes this is suppressed and that it has excellent light resistance. Based on this knowledge, the inventors have further studied and completed the present invention.

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

(in the general formula (1), R ^1a , R ^1b , R ^2a and R ^2b each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms and optionally having a substituent; R ^3a and R ^3b each independently represent an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms,
R ⁵¹ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, or an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, and R ⁶¹ is 6 carbon atoms. represents an optionally substituted aryl group of up to 20, R ⁶² represents a linear or branched alkyl group optionally having 1 to 20 carbon atoms, and X is represents a halogen atom. )

In the present invention, R ⁶¹ in general formula (1) above is preferably a phenyl group.

In the present invention, R ⁶² in general formula (1) above is more preferably a methyl group or an ethyl group.

In the present invention, it is preferable that R ^3a and R ^3b in the general formula (1) are each independently a linear or branched alkyl group having 1 to 5 carbon atoms.

In the present invention, X in general formula (1) above is preferably a fluorine atom.

The boron complex compound of the present invention preferably has a maximum absorption wavelength of 480 to 520 nm when dissolved in chloroform.

In the boron complex compound of the present invention, when the absorbance at the absorption maximum wavelength of the solution dissolved in chloroform is 1, the absorbance at a wavelength of 560 nm with respect to the absorption maximum wavelength is preferably 0.03 or less.

The boron complex compound of the present invention is preferably a dye compound.

An optical filter of the present invention is characterized by containing the boron complex compound of the present invention.

The optical filters of the present invention are preferably spectacle lenses or color correction filters.

According to the present invention, it is possible to provide a boron complex compound that can selectively absorb light with a wavelength of 480 to 520 nm, suppresses fluorescence that causes a decrease in contrast, and has excellent light resistance. can.

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

(in the general formula (1), R ^1a , R ^1b , R ^2a and R ^2b each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms and optionally having a substituent; R ^3a and R ^3b each independently represent an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms,
R ⁵¹ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, or an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, and R ⁶¹ is 6 carbon atoms. represents an optionally substituted aryl group of up to 20, R ⁶² represents a linear or branched alkyl group optionally having 1 to 20 carbon atoms, and X is represents a halogen atom. )

In general formula (1), R ^1a , R ^1b , R ^2a and R ^2b each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms and optionally having a substituent. In the present specification, the number of carbon atoms is the number of carbon atoms in the entire group including substituents.
The linear or branched alkyl group is not particularly limited, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, 1-methylpropyl, t- butyl group, n-pentyl group, 3-methylbutyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, n-hexyl group, 4-methyl pentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethyl butyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, n -heptyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group, n-octyl group, 2-ethylhexyl group, 2,5 -dimethylhexyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, t-octyl group, n-nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, 4- ethyloctyl group, 4-ethyl-4,5-dimethylhexyl group, n-undecyl group, n-dodecyl group, 1,3,5,7-tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyl Octyl group, n-tridecyl group, 6-methyl-4-butyloctyl group, n-tetradecyl group, n-pentadecyl group, 3,5-dimethylheptadecyl group, 2,6-dimethylheptadecyl group, 2,4- dimethylheptadecyl group, 2,2,5,5-tetramethylhexyl group and the like.

Substituents in the optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms are not particularly limited, for example, monocyclic or polycyclic aromatic ring groups having 6 to 10 carbon atoms. (phenyl group, naphthyl group, etc.), linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, amino group, mono- or di-alkylamino group (alkyl has 1 to 8 carbon atoms), halogen atom, Cyano group, hydroxy group, nitro group, carboxy group, alkoxycarbonyl group having 1 to 8 carbon atoms, acyl group having 2 to 10 carbon atoms (e.g., acetyl group, propionyl group, butyryl group, valeryl group, pivaloyl group, acryloyl group , methacryloyl group, benzoyl group, toluoyl group, cinnamoyl group, anisoyl group, naphthoyl group, etc.), acyloxy group having 2 to 10 carbon atoms, 2-propen-1-yl group, 1-oxopropen-1-yl group, 1 -oxo-2-propen-1-yloxy group, 4-ethenylphenylmethoxy group and the like.
Among them, R ^1a , R ^1b , R ^2a and R ^2b are each independently preferably a methyl group, an ethyl group or a propyl group, more preferably a methyl group.

In general formula (1), R ^3a and R ^3b each independently represent an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms.
Examples of the optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms include those described for R ^1a , R ^1b , R ^2a and R ^2b .
Among them, R ^3a and R ^3b are preferably each independently a linear or branched alkyl group having 1 to 5 carbon atoms, such as ethyl group, 3-methylbutyl group, n-propyl group, isopropyl group, n-butyl group, 1-methylpropyl group, 2-methylpropyl group or n-pentyl group is more preferred, and ethyl group or 3-methylbutyl group is even more preferred.

In general formula (1), R ⁵¹ , R ⁵² , R ⁵³ and R ⁵⁴ are each independently a hydrogen atom, a halogen atom, or a linear or branched chain optionally having a substituent having 1 to 20 carbon atoms. represents an alkyl group of
Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine atoms.
In addition, examples of the optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms include the same as those described for R ^1a , R ^1b , R ^2a and R ^2b .
Among them, R ⁵¹ , R ⁵² , R ⁵³ and R ⁵⁴ are each independently preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, an ethyl group or a trifluoromethyl group, and preferably a hydrogen atom. is more preferred.

In general formula (1), R ⁶¹ represents an optionally substituted aryl group having 6 to 20 carbon atoms.
The aryl group is not particularly limited and includes, for example, monocyclic aromatic hydrocarbon groups such as phenyl group; groups.
Substituents in the optionally substituted aryl group having 6 to 20 carbon atoms are not particularly limited. alkoxy group, amino group, mono- or di-alkylamino group (alkyl has 1 to 8 carbon atoms), halogen atom, cyano group, hydroxy group, nitro group, halogenated hydrocarbon group having 1 to 8 carbon atoms, carboxy groups, alkoxycarbonyl groups having 1 to 8 carbon atoms, and the like. A linear, branched or cyclic alkyl group having 1 to 8 carbon atoms and a halogen atom are preferred. Examples of substituted phenyl and naphthyl groups include nitrophenyl, cyanophenyl, hydroxyphenyl, methylphenyl, dimethylphenyl, trimethylphenyl, fluorophenyl, chlorophenyl, and dichlorophenyl groups. , bromophenyl group, methoxyphenyl group, ethoxyphenyl group, trifluoromethylphenyl group, N,N-dimethylaminophenyl group, nitronaphthyl group, cyanonaphthyl group, hydroxynaphthyl group, methylnaphthyl group, fluoronaphthyl group, chloronaphthyl group, bromonaphthyl group, trifluoromethylnaphthyl group, and the like.
Among them, R ⁶¹ is preferably a phenyl group, a chlorophenyl group or a methylphenyl group, more preferably a phenyl group.

In general formula (1), R ⁶² represents an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms.
Examples of the optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms include those described for R ^1a , R ^1b , R ^2a and R ^2b .
Among them, R ⁶² is preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, 1-methylpropyl group, 2-methylpropyl group or t-butyl group. or an ethyl group is more preferred.

In general formula (1), X represents a halogen atom.
Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine atoms.
Among them, X is preferably a fluorine atom.

A boron complex compound represented by the general formula (1) can be produced, for example, by the following method.
A compound represented by the following general formula (2) (hereinafter also referred to as compound (2)) and a compound represented by the following general formula (3) (hereinafter also referred to as compound (3)) and / or the following general formula The compound represented by (4) (hereinafter also referred to as compound (4)) is stirred in a solvent in the presence of an acid catalyst and then oxidized using an oxidizing agent to give the following general formula (5 ) (hereinafter also referred to as compound (5)) can be obtained.
Thereafter, compound (1) of the present invention can be produced by reacting compound (5) with a boron halide derivative.

In the general formulas (2) and (5), substituents with a lowercase letter c after the number, such as R ^51c and R ^61c , are represented by an alphabet after the number in the description of the general formula (1). It is meant to have the same structure as the substituents without lower case letters (R ⁵¹ for R ^51c and R ⁶¹ for R ^61c ).
Further, in general formulas (3) and (5), substituents with a lowercase letter d after the number, such as R ^1d and R ^2d , are has the same structure as the substituent (R ^1a in the case of R ^1d and R ^2a in the case of R ^2d ) attached with a lowercase letter a.
Further, in the general formulas (4) and (5), substituents with a lowercase letter e after the number such as R ^1e and R ^2e are has the same structure as the substituent (R ^1b in the case of R ^1e and R ^2b in the case of R ^2e ) attached with a lowercase letter b.
That is, R ^51c , R ^52c , R ^{53c , R 54c ,} R ^61c and R ^62c in general formulas (2) and (5) are equivalent to R ⁵¹ , R ⁵² , R ^{53 in general formula (1),} Each has the same meaning as R ⁵⁴ , R ⁶¹ and R ⁶² . Preferred embodiments of R ^51c , R ^{52c , R 53c} , R ^54c , R ^61c and R ^62c are the same as the preferred embodiments of R ⁵¹ , R ⁵² , R ^{53 ,} R ⁵⁴ , R ⁶¹ and R ⁶² above.
R ^1d , R ^2d and R ^3d in general formulas (3) and (5) are synonymous with R ^1a , R ^2a and R ^3a in general formula (1), respectively. Preferred embodiments of R ^1d , R ^2d and R ^3d are the same as the preferred embodiments of R ^1a , R ^2a and R ^3a above.
R ^1e , R ^2e and R ^3e in general formulas (4) and (5) are synonymous with R ^1b , R ^2b and R ^3b in general formula (1), respectively. Preferred embodiments of R ^1e , R ^2e and R ^3e are the same as the above preferred embodiments of R ^1b , R ^2b and R ^3b respectively.

Acid catalysts that can be used in the production method include, for example, hydrochloric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, and hydrobromic acid.

The solvent that can be used in the above production method may be any inert solvent, such as halogen solvents (methylene chloride, dichloroethane, etc.), toluene, acetonitrile, alcohol solvents (methanol, ethanol, isopropyl alcohol, etc.), and the like. is mentioned.

Examples of oxidizing agents that can be used in the above production method include chloranil (2,3,5,6-tetrachloro-p-benzoquinone), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), Oxygen-containing gas (air etc.) etc. are mentioned.

Examples of boron halide derivatives that can be used in the production method include boron trifluoride diethyl ether complex.

The reaction conditions for obtaining compound (5) from compound (2) and compound (3) and/or compound (4) are not particularly limited, but for example, the temperature may be 10 to 60°C. preferable. The reaction time is preferably 0.5 to 12 hours.
Further, the reaction conditions for obtaining the compound (1) of the present invention by reacting the compound (5) with a boron halide derivative are not particularly limited, but for example, room temperature to 70° C. is preferable. . The reaction time is preferably 0.5 to 24 hours.

Isolation and purification of each product in the above production method can be carried out by appropriately combining methods used in ordinary organic synthesis, such as filtration, extraction, washing, drying, concentration, crystallization, various types of chromatography, and the like. Further, intermediates can be subjected to the next reaction without particular purification.

Compound (1) of the present invention is excellent in light resistance.
Therefore, the compound (1) of the present invention has the property of being difficult to be decomposed by light.
Specifically, it is preferable that the storage rate after 8 hours in the light resistance test is 40% or more.
The storage rate in the light resistance test can be measured by the method described in Examples.

Compound (1) of the present invention has a low fluorescence intensity.
Therefore, it is possible to suppress the generation of fluorescence that deteriorates the contrast.
Evaluation of fluorescence intensity can be performed, for example, by the following method.
The compound (1) of the present invention was dissolved in an 8% by weight toluene solution of PMMA (polymethyl methacrylate), coated on a glass substrate by spin coating and dried to prepare a thin film of 1.5 μm, and the absorption of the thin film was The amount of compound (1) added is adjusted so that the maximum transmittance is about 25%. On the other hand, a thin film having a thickness of 1.5 μm is produced in the same manner for the following general formula (1-A). For each thin film produced, the fluorescence spectrum is measured with the absorption maximum wavelength as the wavelength of the excitation light source, and the fluorescence intensity at the fluorescence peak wavelength of the thin film of the following general formula (1-A) is set to 1, and the relative value is obtained. Strength can be evaluated.
Compound (1) of the present invention preferably has a relative value of less than 5, more preferably less than 2.5.
As a measuring instrument, a fluorescence spectrophotometer FluoroMax-4 manufactured by Horiba, Ltd. can be used.

Compound (1) of the present invention preferably has a maximum absorption wavelength of 480 to 520 nm.
When the maximum absorption wavelength is 480 to 520 nm, blue-green light can be effectively absorbed. When such a compound is used, for example, in an optical filter for an image display device, it can absorb unnecessary light in the intermediate wavelength region between blue and green and improve the color purity of light transmitted through the color filter.
Compound (1) of the present invention more preferably has a maximum absorption wavelength of 490 to 510 nm.
The maximum absorption wavelength can be measured by the method described in Examples.

Assuming that the absorbance at the maximum absorption wavelength is 1, the compound (1) of the present invention preferably has an absorbance of 0.04 or less at a wavelength of 560 nm with respect to the maximum absorption wavelength.
Assuming that the absorbance at the maximum absorption wavelength is 1, if the absorbance at a wavelength of 560 nm with respect to the maximum absorption wavelength is 0.04 or less, when used in an optical filter, blue-green light can be obtained without reducing the transmittance of green light. Since it can selectively absorb light, the contrast between blue and green can be further improved.
Compound (1) of the present invention preferably has an absorbance of 0.03 or less at a wavelength of 560 nm relative to the maximum absorption wavelength when the absorbance at the maximum absorption wavelength of a solution dissolved in chloroform is set to 1. Absorbance can be measured by the method described in Examples.

Compound (1) of the present invention is preferably a compound that dissolves in an organic solvent.
Examples of organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.), ketones (e.g., 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, 3-methoxypropion methyl acid, etc.) and mixed solvents of two or more thereof.
The compound (1) of the present invention preferably dissolves in at least one of the above organic solvents by 0.1% by mass or more, for example, preferably 0.1% by mass or more and 50% by mass or less. It is more preferable to dissolve 2% to 30% by mass, and more preferably 2% to 30% by mass. More preferably, the solubility in organic solvents at 20°C is within this range. When the solubility in an organic solvent is in such a range, the compound (1) of the present invention is preferable because it has good manufacturability when used for manufacturing an optical filter such as a spectacle lens.

Since the compound (1) of the present invention has the properties as described above, it can be suitably used as a dye compound.

The compound (1) of the present invention can be made into a dye composition by mixing with, for example, a resin. A dye composition is suitably used as a coloring composition.
The resin is not particularly limited, and a thermoplastic resin, a photocurable resin, a thermosetting resin, or the like may be appropriately selected according to the intended use of the coloring composition. For example, acrylic resin, polycarbonate resin, polystyrene resin, low-density polyethylene resin, polypropylene resin, polyurethane resin, polyamide resin, polyacetal resin, polyphenylene sulfide resin, polyethylene terephthalate resin, polybutylene terephthalate resin, polycycloolefin resin, polysulfone resin, poly Resins such as ether sulfone resins, fluororesins, silicone resins, polyester resins, epoxy resins, phenol resins and melamine resins can be used. These may be used alone or in combination of two or more.

The amount of the compound (1) of the present invention in the dye composition is, for example, preferably 0.001 to 50% by mass of the compound with respect to the total solid content of the dye composition, and 0.01 to 40% by mass. % is more preferred.

The dye composition may contain optional components other than the compound (1) of the present invention and the resin, depending on its use. Optional components include, for example, antioxidants, antifoaming agents, other dyes (dyes, pigments, etc.), ultraviolet absorbers, infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers, and the like.
The method for producing the dye composition is not particularly limited, and for example, the compound (1) of the present invention, a resin, and optional ingredients blended as desired may be mixed.

The compound (1) of the present invention and the dye composition containing the same are suitably used, for example, for producing optical filters and the like. An optical filter or the like containing the compound (1) of the present invention is also included in the present invention. The optical filter is not particularly limited as long as it contains the compound (1) of the present invention.
The optical filter is not particularly limited, and examples thereof include lenses such as spectacle lenses, color filters, color correction filters, and color conversion filters. Spectacles also include sunglasses and sports goggles. These optical filters can be suitably used for spectacles (including sunglasses and goggles), imaging devices, lighting tools, display devices, and the like. Among them, the compound (1) of the present invention is effective in improving the contrast between blue and green of objects to be visually observed, and therefore is preferably used for spectacle lenses and color correction filters.

The optical filter may contain the compound (1) of the present invention, and may have a support and, if necessary, an optical functional layer, etc., as in conventional filters. In the optical filter, the compound (1) of the invention is preferably contained in the support or the optical functional layer.

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

A manufacturing method of the optical filter is not particularly limited. For example, as a method of forming an optical functional layer containing the compound (1) of the present invention on a support, the compound (1) of the present invention and a binder resin or the like are dissolved or dispersed in a solvent, followed by a dip coating method, A coating method such as an air knife coating method, a curtain coating method, a roller coating method, a wire bar coating method, a gravure coating method, a spin coating method and an extrusion coating method may be used to form a coating film on a support. Examples of the solvent include, but are not particularly limited to, the above-described organic solvents.

Further, as a method for producing an optical functional layer or support containing the compound (1) of the present invention, the compound (1) of the present invention, a photocurable resin and/or a thermosetting resin, and a photopolymerization initiator and/or After mixing with a thermal polymerization initiator, a cured film can be formed by light irradiation and/or heat treatment, and this can be used as an optical function layer or support.

Examples of a method for producing a lens, which is an example of an optical filter, include a method of kneading the compound (1) of the present invention into a transparent resin and molding by an injection molding method, a compression molding method, an extrusion molding method, or the like; Various methods such as a method of forming an optical functional layer containing the compound (1) of the present invention on a support can be employed.

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

The equipment and measurement conditions used to measure the physical properties of the obtained compounds are as follows.
(LC/MS)
Shimadzu Corp. High performance liquid chromatograph mass spectrometer LCMS-2010EV (ESI method)

<Comparative Example 1>
A compound [compound (1-1)] represented by the following formula (1-1) was produced by the following method. Hereinafter, the compound represented by formula (1-1) is also referred to as compound (1-1). The same applies to compounds of other formula numbers.
In the formula, Ph represents a phenyl group, Me represents a methyl group, and Et represents an ethyl group.
In a 100 mL four-necked flask equipped with a thermometer, the compound represented by the following formula (2-1) (1.4 g), the compound represented by the following formula (3-1) (1.7 g), trifluoro Acetic acid (0.1 g) and methylene chloride (50 mL) were mixed and stirred at room temperature for 1 hour, DDQ (1.3 g) was added and stirred for 30 minutes, then discharged into water and extracted with chloroform. An extract containing the compound represented by (4-1) was obtained. The extract was dissolved in methylene chloride (30 mL), triethylamine (5 g) and boron trifluoride diethyl ether (11.2 g) were added, and the mixture was stirred at room temperature for 2.5 hours, then discharged into water and extracted with chloroform. A compound (1-1) was obtained.
LC-MS: m/z = 636 [M+H] ⁺

<Comparative Example 2>
Compound (1-2) was obtained in the same procedure except that compound (3-1) in the production of compound (1-1) was changed to compound (3-2).
LC-MS: m/z = 720 [M+H] ⁺

<Comparative Example 3>
In the same procedure except that compound (2-1) in the production of compound (1-1) was changed to compound (2-2) and compound (3-1) was changed to compound (3-2), compound (1 -3) was obtained.
LC-MS: m/z = 624 [M+H] ⁺

<Example 1>
Compound (1-4) was obtained in the same procedure except that compound (2-1) in the production of compound (1-1) was changed to compound (2-3).
LC-MS: m/z=588 [M+H] ⁺

<Example 2>
In the same procedure except that compound (2-1) in the production of compound (1-1) was changed to compound (2-4) and compound (3-1) was changed to compound (3-2), compound (1 -5) was obtained.
LC-MS: m/z = 658 [M+H] ⁺

<Example 3>
In the same procedure except that compound (2-1) in the production of compound (1-1) was changed to compound (2-3) and compound (3-1) was changed to compound (3-2), compound (1 -6) was obtained.
LC-MS: m/z = 672 [M+H] ⁺

The compounds obtained above were evaluated as follows. Table 1 shows the results.

<Absorption wavelength measurement test>
For each compound obtained in Examples and Comparative Examples, the absorption spectrum in chloroform was measured to determine the maximum absorption wavelength (λmax) at a wavelength of 400 to 800 nm.
The absorption spectrum and maximum absorption wavelength were measured using a UV-visible spectrophotometer V-560 manufactured by JASCO Corporation.
In addition, the relative value of the absorbance at a wavelength of 560 nm was obtained when the absorbance at the maximum maximum wavelength (λmax) was set to 1.
The relative value of absorbance at a wavelength of 560 nm was evaluated according to the following criteria.
A: relative value is 0.03 or less B: relative value is greater than 0.03, 0.04 or less C: relative value is greater than 0.04

<Light resistance test>
Each compound obtained in Examples and Comparative Examples was subjected to a light resistance test.
10 mg of each compound was melted in 5 mL of an 8% by weight toluene solution of polymethyl methacrylate, applied onto a glass substrate by spin coating, and dried to prepare a thin film having a thickness of 1.5 μm.
The prepared thin film was continuously irradiated with light from a xenon lamp (142 klux) for 8 hours, and the transmittance of the thin film before irradiation (0 hour) and after irradiation was measured with a spectrophotometer, and the dye was stored according to the following formula (I). rate was measured.
Dye storage rate (%) = {(1-T ₁ )/(1-T ₀ )} x 100 (I)
[where T ₀ is the transmittance before xenon lamp irradiation, T ₁ is the transmittance after xenon lamp irradiation, and T ₀ and T ₁ are 0 to 1. ]
The term "transmittance" refers to the transmittance of each compound at the absorption maximum wavelength, and the higher the dye residual rate, the more difficult the compound to decompose by light and the higher the light resistance.
The light resistance was evaluated according to the following criteria.
A: Pigment preservation rate is 40% or more B: Pigment preservation rate is 20% or more and less than 40% C: Pigment preservation rate is less than 20%

<Fluorescence intensity evaluation test>
Fluorescence intensity was measured for each compound obtained in Examples and Comparative Examples. Each compound was dissolved in an 8% by weight toluene solution of PMMA (polymethyl methacrylate), applied onto a glass substrate by spin coating, and dried to form a thin film of 1.5 μm. At this time, the amount of each compound added was adjusted so that the transmittance at the absorption maximum of the thin film was about 25%. Fluorescence spectra of each of the prepared thin films were measured with the maximum absorption wavelength as the wavelength of the excitation light source. As a measurement instrument, a fluorescence spectrophotometer FluoroMax-4 manufactured by Horiba, Ltd. was used.
In addition, the fluorescence intensity was evaluated according to the following criteria.
A: Relative value less than 2.5 B: Relative value 2.5 or more and less than 5 C: Relative value 5 or more

From the above results, it was confirmed that the compounds produced in Examples have a maximum absorption wavelength of 480 to 520 nm and low absorbance at 560 nm, and can selectively absorb light in the range of 480 to 520 nm. In addition, it was found that the compounds produced in Examples have good light resistance and low fluorescence intensity, and thus can be used as dyes for optical filters.
On the other hand, the compounds of Comparative Examples 1 and 2 had insufficient light resistance and high fluorescence intensity. In addition, the compound of Comparative Example 3 had a high absorbance at 560 nm.

Claims (10)

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

(in the general formula (1), R ^1a , R ^1b , R ^2a and R ^2b each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms and optionally having a substituent; R ^3a and R ^3b each independently represent an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms,
R ⁵¹ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, or an optionally substituted linear or branched alkyl group having 1 to 20 carbon atoms, and R ⁶¹ is 6 carbon atoms. represents an optionally substituted aryl group of up to 20, R ⁶² represents a linear or branched alkyl group optionally having 1 to 20 carbon atoms, and X is represents a halogen atom. ) 2. The boron complex compound according to claim 1, wherein ^R61 in the general formula (1) is a phenyl group. 3. The boron complex compound according to claim 1, wherein ^R62 in the general formula (1) is a methyl group or an ethyl group. 4. The boron complex compound according to any one of claims 1 to 3, wherein R ^3a and R ^3b in the general formula (1) are each independently a linear or branched alkyl group having 1 to 5 carbon atoms. 5. The boron complex compound according to any one of claims 1 to 4, wherein X in the general formula (1) is a fluorine atom. The boron complex compound according to any one of claims 1 to 5, wherein a solution dissolved in chloroform has a maximum absorption wavelength of 480 to 520 nm. The boron complex compound according to any one of claims 1 to 6, wherein the absorbance at a wavelength of 560 nm with respect to the maximum absorption wavelength is 0.03 or less when the absorbance at the absorption maximum wavelength of the solution dissolved in chloroform is 1. The boron complex compound according to any one of claims 1 to 7, which is a dye compound. An optical filter comprising the boron complex compound according to any one of claims 1 to 8. 10. The optical filter according to claim 9, which is a spectacle lens or a color correction filter.