Compound having naphthalene rings, optical film, coating material, and ink

Abstract

The present invention provides a compound having naphthalene rings which is useful as an optical material. Also provided are an optical film, a coating material, and an ink which contain the compound having naphthalene rings. This compound having naphthalene rings is represented by formula (1). In formula (1), R1, R2, R3, R4, R5, R6, R7, and R8 each independently represent a hydrogen atom, a C20 or lower alkyl group, or an amino group in which one or more of the hydrogen atoms may have been replaced with other structure. In formula (1), Ra represents a hydrogen atom, a C20 or lower alkyl group, or an oxo group (=O) and Rb represents a hydrogen atom, a C20 or lower alkyl group, or an imino group in which the hydrogen atom may have been replaced with a structure having an aromatic ring.　

Description

Compounds having a naphthalene ring, optical films, paints and inks

[0001] The present invention relates to a compound having a naphthalene ring, an optical film, a paint, and an ink.

[0002] Carbon black has traditionally been used as a black material, with other materials such as iron oxide black (iron tetroxide) also being used. These materials exhibit a black color and absorb light with wavelengths ranging from the visible light region to the far-infrared region. Therefore, articles such as coatings colored with these black materials are prone to becoming hot due to the absorption of sunlight. Furthermore, because carbon black is electrically conductive, articles colored with carbon black have poor electrical insulation properties. Meanwhile, with the use of infrared laser radiation and the development of corresponding sensors in the fields of electronics and optical devices, many fields are seeking black materials with properties not found in conventional black materials such as carbon black. For example, in infrared communications, infrared camouflage, and optical filters, oil-soluble dyes have been used as coloring materials for infrared-transmitting filters. However, these oil-soluble dyes have problems with durability, such as heat resistance, solvent resistance, and light resistance. Therefore, dark-colored materials with excellent durability and infrared transmittance are needed.

[0003] In particular, black materials that have sufficient transparency to light rays having wavelengths from near-infrared to infrared have been put to practical use. For example, Patent Document 1 describes a dark azo pigment obtained by a coupling reaction between 2-hydroxy-11H-benzo[a]carbazole-3-carboxy-N-benzimidazolone-5-amide as a coupling component and a known diazo compound as a diazo component. Furthermore, Patent Document 2 describes a black azo pigment having a volume fraction of 2% to 30% by volume, an average dispersed particle diameter in a film of 1 nm to 200 nm, an optical density per μm thickness of 1 or more, and a volume resistivity of 10 １１ Patent Document 3 describes a composition for a color filter containing a near-infrared-transmitting black coloring material, and describes a bisbenzofuranone-based pigment as the near-infrared-transmitting black coloring material.

[0004] International Publication No. 2010 / 044393 International Publication No. 2012 / 026577 Japanese Patent Application Laid-Open No. 2014-130173

[0005] As optical materials, the use of new materials different from the materials described in Patent Documents 1 to 3 has been considered, and new materials useful as optical materials are desired.

[0006] In view of the above-described current situation, an object of the present invention is to provide a compound having a naphthalene ring that is useful as an optical material, and an optical film, a paint, and an ink that contain the compound having a naphthalene ring.

[0007] The present disclosure (1) is a compound having a naphthalene ring represented by the following formula (1). In formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ and R ８ each independently represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an amino group in which the hydrogen atom may be substituted with another structure. In formula (1), Ra represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an oxo group (=O), and Rb represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an imino group in which the hydrogen atom may be substituted with a structure having an aromatic ring. The present disclosure (2) is a compound having a naphthalene ring of the present disclosure (1) in which Ra is an oxo group (=O) in formula (1). The present disclosure (3) is a compound having a naphthalene ring of the present disclosure (1) or (2) in which Rb in formula (1) is an imino group represented by the following formula (2): In formula (2), Rb １ represents a single bond, a heteroatom, or an alkylene group having 5 or less carbon atoms; Rb ２ and Rb ３ are each independently a hydrogen atom, -ORb １１ , -NRb １２ Rb １３ Rb １１ , Rb １２ , Rb １３are each independently a hydrogen atom, an aldehyde group, an alkyl group having 20 or less carbon atoms, or —CH ２ -Rx, -CH=N-Ry, and an aromatic group, and Rx and Ry each independently represent a structure of the following formula (3) or (4). In formula (3), Rx １ and Rx ２ each independently represents a hydrogen atom or an alkyl group having 20 or less carbon atoms. １ and Ry ２ Each independently represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an aromatic group having 20 or less carbon atoms and containing a benzene ring. １ , R ２ , R ３ , R ４ , R ５ , R ７ and R ８ The present disclosure (5) is a compound having a naphthalene ring according to any one of the disclosures (1) to (3), wherein R ６ is a hydrogen atom or a structure of the following formula (5), and is a compound having a naphthalene ring according to any one of (1) to (5) of the present disclosure. The present disclosure (6) is a compound having a naphthalene ring of the present disclosure (3), represented by the following formula (6). In formula (6), Rz １ represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an amino group in which the hydrogen atom may be substituted with another structure; Rz ２ is Rb in the above formula (2) ２ The present disclosure (7) is an optical film containing a compound having a naphthalene ring according to any one of the present disclosures (1) to (6). The present disclosure (8) is a paint containing a compound having a naphthalene ring according to any one of the present disclosures (1) to (6). The present disclosure (9) is an ink containing a compound having a naphthalene ring according to any one of the present disclosures (1) to (6). The present invention will be described in detail below.

[0008] As a result of extensive investigations, the present inventors have produced a novel compound having a naphthalene ring represented by the above formula (1) as an optical material, thereby completing the present invention.

[0009] The compound having a naphthalene ring of the present invention is a compound represented by the following formula (1).

[0010] In formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ and R ８ each independently represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an amino group in which the hydrogen atom may be substituted with another structure. In formula (1), Ra represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an oxo group (═O), and Rb represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an imino group in which the hydrogen atom may be substituted with a structure having an aromatic ring.

[0011] Examples of the alkyl group having 20 or less carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group.

[0012] The above R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ is preferably a hydrogen atom or an alkyl group having 5 or less carbon atoms, and more preferably a hydrogen atom.

[0013] The above Ra is preferably a hydrogen atom, an oxo group (═O), or an alkyl group having 5 or less carbon atoms, and more preferably an oxo group. The above Rb is preferably a hydrogen atom, an alkyl group having 5 or less carbon atoms, or an imino group in which the hydrogen atom may be substituted with a structure having an aromatic ring, and more preferably an imino group in which the hydrogen atom may be substituted with a structure having an aromatic ring.

[0014] When Rb is an imino group in which a hydrogen atom may be substituted with a structure having an aromatic ring, Rb is preferably an imino group represented by the following formula (2).

[0015]

[0016] In formula (2), Rb １ represents a single bond, a heteroatom, or an alkylene group having 5 or less carbon atoms; Rb ２ and Rb ３ are each independently a hydrogen atom, -ORb １１ , -NRb １２ Rb １３ Rb １１ , Rb １２ , Rb １３ are each independently a hydrogen atom, an aldehyde group, an alkyl group having 20 or less carbon atoms, or —CH ２ -Rx and -CH=N-Ry represent an aromatic group, and Rx and Ry each independently represent a structure of the following formula (3) or (4): In the aromatic group, a hydrogen atom may be substituted with a hydroxyl group, an oxygen atom, or the like, and examples thereof include a phenyl group and a naphthyl group.

[0017]

[0018] In the above formula (3), Rx １ and Rx ２ Each of R and R independently represents a hydrogen atom or an alkyl group having 20 or less carbon atoms. １ and Ry ２ each independently represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an aromatic group having 20 or less carbon atoms and containing a benzene ring.

[0019] In the above formula (2), Rb １ In the above formula (2), Rb is preferably a single bond. ２ Ha-NRb １２ Rb １３ In addition, Rb １２ , Rb １３ is preferably a hydrogen atom, an aldehyde group or a methyl group.

[0020] In the above formula (3), Rx １ and Rx ２are each independently preferably a hydrogen atom or an alkyl group having 5 or less carbon atoms, more preferably a hydrogen atom or a methyl group. １ and Ry ２ is preferably a hydrogen atom or an alkyl group having 5 or less carbon atoms, more preferably a hydrogen atom or a methyl group.

[0021] In the above formula (1), R ６ is preferably a hydrogen atom or a structure of the following formula (5).

[0022]

[0023] The compound having a naphthalene ring is preferably a compound represented by the following formula (6).

[0024]

[0025] In formula (6), Rz １ represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an amino group in which the hydrogen atom may be substituted with another structure; Rz ２ is Rb in the above formula (2) ２ is the same as:

[0026] More specifically, the compounds having a naphthalene ring include compounds represented by the following formulas (7) to (12).

[0027]

[0028] The compound having a naphthalene ring represented by the above formula (1) can be prepared by mixing and reacting a compound having a naphthalene ring containing a hydroxy group represented by the following formula (13), an oxidizing agent, other additives such as a dispersant, etc. Furthermore, it is preferable to mix a compound having an aromatic ring containing an amino group represented by the following formula (14).

[0029]

[0030] Ra in the above formula (13) １ , Ra ２ , Ra ３ , Ra ４ is R in the above formula (1) １ , R ２ , R ３ , R ４ , R ５, R ６ , R ７ , R ８ is the same as:

[0031] The compound having a naphthalene ring containing a hydroxy group may be used alone or in combination of two or more, but it is preferable to use one.

[0032]

[0033] The above Rc １ , Rc ２ is the Rb in the formula (2). ２ , Rb ３ is the same as:

[0034] The compound having an aromatic ring containing an amino group may be used alone or in combination of two or more kinds, but it is preferable to use one kind.

[0035] In the above reaction, the amount of the compound having a naphthalene ring containing a hydroxy group added relative to 100 parts by weight of the compound having an aromatic ring containing an amino group is preferably 100 parts by weight or more, more preferably 200 parts by weight or more, and is preferably 1,000 parts by weight or less, more preferably 800 parts by weight or less.

[0036] The solvent used in the above reaction may be water, ethanol, n-propanol, isopropanol, N-methylpyrrolidone (NMP), acetone, dimethyl sulfoxide, acetonitrile, pyridine, etc. Of these, water is preferred.

[0037] In the above reaction, the amount of the solvent added relative to 100 parts by weight of the compound having an aromatic ring containing an amino group is preferably 5,000 parts by weight or more, more preferably 10,000 parts by weight or more, and is preferably 100,000 parts by weight or less, more preferably 50,000 parts by weight or less.

[0038] In the above reaction, an oxidizing agent is further added to the compound having a naphthalene ring containing a hydroxyl group, and the reaction is carried out. This allows the compound having a naphthalene ring to be produced. In addition, in the above reaction, it is preferable to mix the compound having an aromatic ring containing an amino group.

[0039] Examples of the oxidizing agent include ketone compounds, peroxides, organic acids, persulfates, nitrates, amine oxide compounds, salts of halogen oxoacids, and hydrazine. Examples of the ketone compounds include quinone compounds such as benzoquinone, 1,2-naphthoquinone, anthraquinone, and chloranil. Examples of the peroxides include hydrogen peroxide and t-butyl hydroperoxide. Examples of the organic acids include formic acid, acetic acid, and propionic acid. Examples of the persulfates include sodium persulfate, potassium persulfate, and ammonium persulfate. Examples of the nitrates include sodium nitrate, ammonium nitrate, and cerium ammonium nitrate. Examples of the amine oxide compounds include N-methylmorpholine N-oxide. Examples of the salts of halogen oxoacids include sodium hypochlorite and sodium chlorite. The oxidizing agents may be used alone or in combination of two or more. Among these, ketone compounds, peroxides, organic acids, persulfates, and hydrazine are preferred. It is also preferable to use a ketone compound and a peroxide in combination. Note that the oxidizing agent is different from the compound having a naphthalene ring containing a hydroxyl group and the compound having an aromatic ring containing an amino group.

[0040] In the reaction, the amount of the oxidizing agent added relative to 100 parts by weight of the compound having an aromatic ring containing an amino group is preferably 20 parts by weight or more, more preferably 100 parts by weight or more, and is preferably 800 parts by weight or less, more preferably 500 parts by weight or less.

[0041] In the reaction, the amount of the oxidizing agent added relative to 100 parts by weight of the compound having a naphthalene ring containing a hydroxy group is preferably 10 parts by weight or more, more preferably 20 parts by weight or more, and is preferably 200 parts by weight or less, more preferably 100 parts by weight or less.

[0042] In the method for preparing the compound having a naphthalene ring, it is preferable to further add a dispersant. Examples of the dispersant include polyvinyl acetal resin, sorbitan monooleate, polyoxyethylene alkyl ether, potassium polyphosphate, sodium polyphosphate, polyacrylic acid, polystyrene sodium sulfonate polyacrylic acid, and acrylamide copolymer. Among them, polyvinyl acetal resin is preferable.

[0043] In the above reaction, the amount of the dispersant added relative to 100 parts by weight of the compound having an aromatic ring containing an amino group is preferably 10 parts by weight or more, more preferably 20 parts by weight or more, and is preferably 1,000 parts by weight or less, more preferably 500 parts by weight or less.

[0044] In the above reaction, the amount of the dispersant added relative to 100 parts by weight of the compound having a naphthalene ring containing a hydroxy group is preferably 5 parts by weight or more, more preferably 10 parts by weight or more, and is preferably 1,000 parts by weight or less, more preferably 500 parts by weight or less.

[0045] In the method for producing the compound having a naphthalene ring, it is preferable to further add a crosslinking agent. Examples of the crosslinking agent include polyamine-based crosslinking agents, thiourea-based crosslinking agents, thiadiazole-based crosslinking agents, triazine-based crosslinking agents, quinoxaline-based crosslinking agents, bisphenol-based crosslinking agents, organic peroxide-based crosslinking agents, aldehyde-based crosslinking agents, and silane-based crosslinking agents. Phenol-based crosslinking agents such as resol phenolic resins can also be used.

[0046] Examples of the polyamine-based crosslinking agents include ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, hexamethylenetetramine, p-phenylenediamine, cumenediamine, N,N'-dicinnamylidene-1,6-hexanediamine, ethylenediamine carbamate, and hexamethylenediamine carbamate. Examples of the thiourea-based crosslinking agents include 2-mercaptoimidazoline (ethylenethiourea), 1,3-diethylthiourea, 1,3-dibutylthiourea, and trimethylthiourea. Examples of the thiadiazole-based crosslinking agents include 2,5-dimercapto-1,3,4-thiadiazole and 2-mercapto-1,3,4-thiadiazole-5-thiobenzoate. Examples of the triazine crosslinking agents include 2,4,6-trimercapto-1,3,5-triazine, 2-hexylamino-4,6-dimercaptotriazine, 2-diethylamino-4,6-dimercaptotriazine, 2-cyclohexylamino-4,6-dimercaptotriazine, 2-dibutylamino-4,6-dimercaptotriazine, 2-anilino-4,6-dimercaptotriazine, and 2-phenylamino-4,6-dimercaptotriazine. Examples of the quinoxaline crosslinking agents include 2,3-dimercaptoquinoxaline, quinoxaline-2,3-dithiocarbonate, 6-methylquinoxaline-2,3-dithiocarbonate, and 5,8-dimethylquinoxaline-2,3-dithiocarbonate. Examples of the bisphenol crosslinking agents include bisphenol AF and bisphenol S. Examples of the organic peroxide crosslinking agent include tert-butyl hydroperoxide, p-menthane hydroperoxide, dicumyl peroxide, tert-butyl peroxide, 1,3-bis(tert-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, benzoyl peroxide, and tert-butyl peroxybenzoate.Examples of the aldehyde crosslinking agents include glyoxal, malondialdehyde, succindialdehyde, maleic dialdehyde, glutaric dialdehyde, formaldehyde, acetaldehyde, benzaldehyde, and 1,3,5-trioxane. Examples of the silane crosslinking agents include alkoxysilanes such as methyltrimethoxysilane, dimethyldimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, and methyltriethoxysilane. Of these, polyamine crosslinking agents and aldehyde crosslinking agents are preferred in terms of ease of addition (solvent solubility) and high reactivity (the carbon atom adjacent to the electron-withdrawing atom is located in a relatively large space (less steric hindrance)).

[0047] In the reaction, the amount of the crosslinking agent added relative to 100 parts by weight of the compound having an aromatic ring containing an amino group is preferably 10 parts by weight or more, more preferably 20 parts by weight or more, and is preferably 1000 parts by weight or less, more preferably 500 parts by weight or less.

[0048] In the above reaction, the amount of the crosslinking agent added relative to 100 parts by weight of the compound having a naphthalene ring containing a hydroxy group is preferably 10 parts by weight or more, more preferably 20 parts by weight or more, and is preferably 1,000 parts by weight or less, more preferably 500 parts by weight or less.

[0049] In the above reaction, when mixing the compound having a naphthalene ring containing a hydroxyl group, the compound having an aromatic ring containing an amino group, the oxidizing agent, the dispersing agent, the crosslinking agent, etc., it is preferable to first mix the compound having a naphthalene ring containing a hydroxyl group and the compound having an aromatic ring containing an amino group, and then add the dispersing agent to the mixture and thoroughly disperse it, and then add the crosslinking agent and the oxidizing agent.

[0050] In the above reaction, the temperature when mixing the materials is preferably 15°C or higher, more preferably 20°C or higher, and preferably 35°C or lower, more preferably 30°C or lower. The stirring time when mixing the materials is preferably 0.2 hours or longer, more preferably 0.3 hours or longer, and preferably 72 hours or shorter, more preferably 60 hours or shorter. Furthermore, the stirring speed when mixing the materials is preferably 200 rpm or higher, more preferably 400 rpm or higher, when using an L30 octagonal stirrer and a φ40 container.

[0051] In the above reaction, after mixing the materials, the mixture is preferably heated to 40° C. or more and 80° C. or less, and stirred, and more preferably heated to 45° C. or more and 65° C. or less. The temperature increase rate during the temperature increase is preferably 0.1° C. / min or more and preferably 3° C. / min or less. The stirring time after the temperature increase is preferably 0.2 hours or more, more preferably 0.5 hours or more, and preferably 5 hours or less, and more preferably 3 hours or less.

[0052] In the above reaction, it is preferable to mix the materials, heat the mixture, and then cool it again. The cooling rate is preferably 0.2°C / min or more and 5°C / min or less.

[0053] Furthermore, it is preferable to separate and purify the reaction product obtained by the above reaction. Separation and purification can be performed using LC / UV and LC / MS. The retention time for separation and purification is preferably 8.5 to 14.5 minutes. Furthermore, the conditions for ultraviolet irradiation during separation and purification include the following: Test equipment: Sunshine Xenon Weather Meter (SX-75 manufactured by Suga Test Instruments Co., Ltd.) Black panel temperature: 63°C Chamber temperature: 50°C Humidity: 50% RH Radiation intensity: 60 W / cm ２ Wavelength range: 300-400 nm Test time: 300 hours The structure of the compound can be adjusted by adjusting the retention time for purification and separation. UV irradiation causes structural changes such as breaking bonds with low interatomic bond energy and generating radicals. In addition, extending the retention time for separation and purification allows more hydrophilic components to be eluted from the column.

[0054] After separation and purification, the compound can be confirmed to be the above-mentioned compound having a naphthalene ring by analysis using nuclear magnetic resonance (NMR), infrared spectroscopy (FT-IR), and mass spectrometry (MS).

[0055] The applications of the compounds having a naphthalene ring are not particularly limited, but they are useful as optical materials, and can be used in applications such as coatings for optical films, black paints, black matrices for color filters, and inks for infrared sensors. In particular, they can be used in applications such as optical films suitable for near-infrared sensors for smartphones, automobiles, and near-infrared cameras. Optical films, paints, and inks containing the compounds having a naphthalene ring also constitute the present invention. When using the compounds having a naphthalene ring to prepare coatings, black paints, black matrices for color filters, inks for infrared sensors, and the like, their light transmittance is affected by the dispersion medium, dispersion method, binder resin used to form the coating, compound content, and coating film thickness. However, hydrophilic to hydrophobic solvents can be selected as the dispersion medium. Furthermore, the compound content is preferably 20 parts by weight or more of particles per 100 parts by weight of binder resin, and the coating film thickness is preferably 30 μm or less.

[0056] The ink can be prepared by, for example, mixing the compound having a naphthalene ring, a solvent, a binder resin, etc. The ink can be applied to a substrate, dried, and molded by removing the solvent, etc., to obtain a molded product such as an optical film.

[0057] Examples of the binder resin include polyvinyl acetal resins such as polyvinyl formal and polyvinyl butyral, (meth)acrylic resins, (meth)acrylic urethane resins, urethane resins, polyvinyl chloride resins, melamine resins, styrene resins, epoxy resins, and polyester resins.

[0058] Examples of a method for producing the optical film include a method in which the compound having a naphthalene ring, a binder resin, a solvent, and the like are mixed using a stirrer or the like to produce a composition containing the compound having a naphthalene ring, and the composition is then applied onto a substrate and dried.

[0059] The method for forming the black matrix involves first mixing the compound having a naphthalene ring, the curable compound, and optionally a curing agent, a solvent, and the like, using a stirrer to prepare a composition containing the compound having a naphthalene ring. The composition is then applied to a substrate and dried to form a coating film. The resulting coating film is partially exposed to active energy rays such as ultraviolet light and excimer laser light through a negative mask, thereby forming a black matrix having a predetermined pattern.

[0060] Furthermore, the above-described method for forming a black matrix can be performed on a photosensitive resin composition having a dispersed red pigment, a photosensitive resin composition having a dispersed green pigment, and a photosensitive resin composition having a dispersed blue pigment to form pixel patterns of each color, thereby forming a color filter. The photosensitive resin composition having a dispersed red pigment, the photosensitive resin composition having a dispersed green pigment, and the photosensitive resin composition having a dispersed blue pigment may be any conventionally known composition. The color filter can also be produced by ejecting red, green, and blue inks from inkjet nozzles into each region defined by the black matrix and curing the accumulated inks with heat or light. The color filter can be suitably used as a component of a display device such as a liquid crystal display device or an organic electroluminescence display device.

[0061] According to the present invention, it is possible to provide a compound having a naphthalene ring that is useful as an optical material, and also to provide an optical film, a paint, and an ink that contain the compound having a naphthalene ring.

[0062] The following examples will further illustrate the present invention, but the present invention is not limited to these examples.

[0063] Example 1: 6.40 g of N,N-dimethyl-1,4-phenylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to 800 g of water, the liquid temperature was raised to 25°C, and the mixture was stirred for 0.5 hours. Next, 22.40 g of 1-naphthol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added and the mixture was stirred for 0.5 hours. Furthermore, 8.69 g of polyvinyl acetal resin powder (S-LEC BL-5Z, manufactured by Sekisui Chemical Co., Ltd.) was added as a dispersant and the mixture was stirred for 0.5 hours. Next, 2.29 g of polyvinyl acetal resin aqueous dispersion (S-LEC KW3, manufactured by Sekisui Chemical Co., Ltd., 20% aqueous dispersion) was added as a dispersant and the mixture was stirred for 6 hours. Thereafter, 9.60 g of 1,3,5-trioxane (manufactured by Tokyo Chemical Industry Co., Ltd.) was added and the mixture was stirred for 15 hours. Next, 11.43 g of hydrogen peroxide water (manufactured by Santoku Chemical Co., Ltd.) was added as an oxidizing agent and stirred for 5 minutes, after which 11.43 g of 1,4-benzoquinone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was further added as an oxidizing agent and stirred for 22 hours. Thereafter, the liquid temperature was raised to 53°C and stirred for 1 hour, and then the liquid temperature was cooled to 25°C at a temperature decrease rate of 1.0°C / min and stirred for 1 hour. The liquid was filtered under reduced pressure and further washed with 100 g of water to obtain a wet cake.

[0064] The obtained wet cake was vacuum dried at 65°C for 3 hours and 20 minutes to obtain a dry solid, which was then pulverized using a Labo Mill OML-2 to obtain a black powder.

[0065] The obtained black powder was irradiated with ultraviolet light under the following conditions to obtain a sample: Test equipment: Sunshine Xenon Weather Meter (SX-75 manufactured by Suga Test Instruments Co., Ltd.), black panel temperature: 63°C, chamber temperature: 50°C, humidity: 50% RH, radiation intensity: 60 W / cm ２ , Wavelength range: 300-400 nm, Test time: 300 hours.

[0066] The obtained sample was used to prepare a 1-2 mg / mL acetone solution, and the soluble matter was separated and purified using LC / UV and LC / MS. The separation and purification conditions were as follows: HPLC: UltiMate3000 [manufactured by Thermo Fisher Scientific], MS: Orbitrap Fusion [manufactured by Thermo Fisher Scientific], analytical column: Xbridge BEH C18 2.1 x 50 mm, 2.5 μm (Imtakt), column temperature: 45 ° C, mobile phase: A: 10 mmol / L ammonium acetate aqueous solution, B: acetonitrile, time program: 0 to 2 minutes: B = 50%, 2 to 8 minutes: B = 50% to 95%, 8 minutes to 25 minutes: B = 95% to 100%, 25 minutes and after: B = 50%, flow rate: 0.3 mL / min, UV detection: PDA (240-800 nm), ionization method: atmospheric pressure chemical ionization (APCI), MS detection range: full scan (m / z 80 to 12000), positive / negative ion detection. The sample injection volume was 3.0 μL, and the retention time of separation and purification was 8.76 ± 0.1 minutes.

[0067] After separation and purification, the obtained black powder particles were analyzed by nuclear magnetic resonance (NMR), infrared spectroscopy (FT-IR), and mass spectrometry (MS), and were confirmed to be the compound represented by the above formula (7).

[0068] Example 2 Black powder particles were obtained in the same manner as in Example 1, except that the retention time for separation and purification was set to 10.43±0.1 minutes. In addition, in the same manner as in Example 1, it was confirmed that the obtained compound was the compound represented by formula (8).

[0069] Example 3 Black powder particles were obtained in the same manner as in Example 1, except that the retention time for separation and purification was set to 13.16±0.1 minutes. In addition, in the same manner as in Example 1, it was confirmed that the obtained compound was the compound represented by formula (9).

[0070] Example 4 Black powder particles were obtained in the same manner as in Example 1, except that ultraviolet irradiation was not performed and the retention time for separation and purification was set to 8.71±0.1 minutes. Furthermore, in the same manner as in Example 1, it was confirmed that the obtained powder particles were the compound represented by the above formula (10).

[0071] Example 5 Black powder particles were obtained in the same manner as in Example 1, except that ultraviolet irradiation was not performed and the retention time for separation and purification was set to 9.83±0.1 minutes. Furthermore, in the same manner as in Example 1, it was confirmed that the obtained black powder particles were the compound represented by the above formula (11).

[0072] Example 6 Black powder particles were obtained in the same manner as in Example 1, except that ultraviolet irradiation was not performed and the retention time for separation and purification was set to 14.17 minutes. Furthermore, in the same manner as in Example 1, it was confirmed that the obtained powder particles were the compound represented by the above formula (12).

[0073] According to the present invention, it is possible to provide a compound having a naphthalene ring that is useful as an optical material, and also to provide an optical film, a paint, and an ink that contain the compound having a naphthalene ring.

Claims

1. A compound having a naphthalene ring represented by the following formula (1): In formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ and R ８ each independently represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an amino group in which the hydrogen atom may be substituted with another structure. In formula (1), Ra represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an oxo group (═O), and Rb represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an imino group in which the hydrogen atom may be substituted with a structure having an aromatic ring.

2. The compound having a naphthalene ring according to claim 1, wherein in formula (1), Ra is an oxo group (=O).

3. A compound having a naphthalene ring according to claim 1 or 2, wherein in formula (1), Rb is an imino group represented by the following formula (2): In formula (2), Rb １ represents a single bond, a heteroatom, or an alkylene group having 5 or less carbon atoms; Rb ２ and Rb ３ are each independently a hydrogen atom, -ORb １１ , -NRb １２ Rb １３ Rb １１ , Rb １２ , Rb １３ are each independently a hydrogen atom, an aldehyde group, an alkyl group having 20 or less carbon atoms, or —CH ２ -Rx, -CH=N-Ry, and an aromatic group, and Rx and Ry each independently represent a structure of the following formula (3) or (4). In formula (3), Rx １ and Rx ２ each independently represents a hydrogen atom or an alkyl group having 20 or less carbon atoms. １ and Ry ２ each independently represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an aromatic group having 20 or less carbon atoms and containing a benzene ring.

4. In formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ７ and R ８ The compound having a naphthalene ring according to any one of claims 1 to 3, wherein is a hydrogen atom.

5. In formula (1), R ６ is a hydrogen atom or a structure represented by the following formula (5):

6. A compound having a naphthalene ring according to claim 3, represented by the following formula (6): In formula (6), Rz １ represents a hydrogen atom, an alkyl group having 20 or less carbon atoms, or an amino group in which the hydrogen atom may be substituted with another structure; Rz ２ is Rb in the above formula (2) ２ Represents.

7. An optical film comprising the compound having a naphthalene ring according to any one of claims 1 to 6.

8. A paint containing the compound having a naphthalene ring according to any one of claims 1 to 6.

9. An ink containing the compound having a naphthalene ring according to any one of claims 1 to 6.

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