+

WO2002034841A1 - Substance permettant d"ameliorer les caracteristiques de resistance a la lumiere - Google Patents

Substance permettant d"ameliorer les caracteristiques de resistance a la lumiere Download PDF

Info

Publication number
WO2002034841A1
WO2002034841A1 PCT/JP2001/009250 JP0109250W WO0234841A1 WO 2002034841 A1 WO2002034841 A1 WO 2002034841A1 JP 0109250 W JP0109250 W JP 0109250W WO 0234841 A1 WO0234841 A1 WO 0234841A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
light
ring
azo
optical recording
Prior art date
Application number
PCT/JP2001/009250
Other languages
English (en)
Japanese (ja)
Inventor
Chiaki Kasada
Yasushi Aizawa
Toshio Kawata
Shigeo Yasui
Original Assignee
Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo filed Critical Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Publication of WO2002034841A1 publication Critical patent/WO2002034841A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only

Definitions

  • the present invention relates to a light resistance improver for styryl dyes, and more particularly to a light resistance improver containing an azo-based organometallic complex.
  • optical recording media such as CD-R (write-once memory using a compact disk) and DVDR- (write-once memory using a digital video disk) have been spotlighted.
  • the optical recording medium is composed of an inorganic optical recording medium that forms the recording layer using an inorganic substance such as tellurium, selenium, rhodium, carbon, and hydrogen sulfide, and an organic recording medium that forms the recording layer using a light absorber mainly composed of an organic dye compound.
  • Optical recording media is composed of an inorganic optical recording medium that forms the recording layer using an inorganic substance such as tellurium, selenium, rhodium, carbon, and hydrogen sulfide, and an organic recording medium that forms the recording layer using a light absorber mainly composed of an organic dye compound.
  • the organic optical recording medium is usually prepared by dissolving a polymethine dye in an organic solvent such as 2,2,3,3-tetrafluoro-1-propanol (hereinafter abbreviated as “TFP”). Is coated on a polycarbonate substrate, dried to form a recording layer, and then a reflective layer made of a metal such as gold, silver, and copper and a protective layer made of an ultraviolet-curable resin are sequentially adhered to form a recording layer.
  • TFP 2,2,3,3-tetrafluoro-1-propanol
  • the disadvantage of organic optical recording media is that the recording layer is more likely to change due to environmental light such as reading light and natural light than inorganic recording media.
  • the recording layer can be formed by directly applying the light absorbing agent in a solution to the substrate, there is an advantage that the optical recording medium can be manufactured at low cost.
  • organic optical recording media are mainly composed of organic substances, they have the advantage of being resistant to corrosion even in environments exposed to moisture and seawater. With the advent of recording media, information recorded on optical recording media in a prescribed format can be read using a commercially available read-only device, and is now becoming the mainstream of inexpensive optical recording media. .
  • a styryl dye that forms an electron conjugated system by a dimethine chain is different from a cyanine dye that forms an electron conjugated system by a polymethine chain such as a trimethine chain or a pentamethine chain in which an odd number of methine groups are connected. It is easy to synthesize those that have appropriate sensitivity to laser light with a wavelength shorter than nm. As a result, it began to attract attention as a light absorber for DVD-R. For example, in Japanese Patent Application Laid-Open Nos. Hei 11-99746, Hei 11-195466 and Hei 11-116995, styryl is used as a light absorbing agent. DVD-R using a dye has been proposed.
  • styryl dyes have low light resistance to reading light, and it is difficult to produce an optical recording medium satisfying the DVD-R standard when used alone. Therefore, in the prior art described above, for example, a transition metal complex, a nitroso compound, an aminium compound, a diimmonium compound, and the like are used in combination in order to improve the light resistance of the styryl dye.
  • these complexes and compounds do not exhibit an effective lightfastness-improving ability with respect to styryl dyes, or even if they exhibit an effective lightfastness-improving ability, they are not sufficiently soluble in organic solvents. There was a problem that it was difficult to handle.
  • an object of the present invention is to provide an easy-to-handle lightfastness improver that effectively improves lightfastness without substantially impairing the light absorption characteristics of a styryl dye, and an application thereof.
  • an azo-based organometallic complex in which one or more azo compounds are bonded to a metal atom (hereinafter referred to as “azo-based organometallic complex”)
  • azo-based organometallic complex When used in combination with a styryl dye, not only can the light resistance be improved without substantially impairing the light absorption properties of the styryl dye, but also the compatibility with the styryl dye in an organic solvent and the thin film state can be improved. It was found to be excellent in amorphous properties and easy to handle.
  • An optical recording medium containing such an azo-based organometallic complex and a styryl dye can store various kinds of information by using a laser beam having a wavelength shorter than 700 nm. It has been found that high-density recording can be performed stably for a long period of time.
  • the present invention solves the above-mentioned problems by providing a styryl dye lightfastness improver containing an azo-based organometallic complex in which one or more azo compounds are bonded to a metal atom. It is. Furthermore, the present invention solves the above-mentioned problems by providing a light absorber comprising such a light resistance improving agent and a styryl dye.
  • the present invention solves the above-mentioned problems by providing an optical recording medium comprising such a light resistance improving agent or a light absorbing agent.
  • a light resistance improving agent or a light absorbing agent it is not known that azo-based organometallic complexes exert such an effect on styryl dyes.
  • the present invention is based on the discovery of a novel use of an azo-based organometallic complex, and a light-stability improving agent for styryl dyes containing an azo-based organometallic complex is the first of this invention. .
  • the azo-based organometallic complex referred to in the present invention is a complex having a metal atom as a central atom, and one or more azo compounds as ligands are bonded to the metal atom.
  • Complex in general.
  • any azo-based organometallic complex which can improve the light resistance of the styryl dye to a practically usable level without substantially impairing the light absorption properties of the styryl dye is considered. It can be used irrespective of the chemical structure and preparation method. When multiple azo compounds are bonded to a metal atom, those azo compounds may be the same or different. You may use it. Examples of such azo-based organometallic complexes include, for example, those represented by the general formula
  • aromatic rings and heterocyclic ring may have one or more substituents.
  • the aromatic ring include a monocyclic or condensed polycyclic aromatic hydrocarbon residue such as a benzene ring, a naphthylene ring and an indandione ring. Of these, a monocyclic ring containing a benzene ring Formulas are preferred.
  • the heterocycle includes one or more heteroatoms selected from a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom.
  • aromatic rings and heterocyclic rings are, for example, methyl group, ethyl group, propyl Group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, tert_pentyl group, 1-methylpentyl group, 2-methylpentyl group, hexyl group Aliphatic hydrocarbon groups such as isohexyl group, 5-methylhexyl group, cycloaliphatic hydrocarbon groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, biphenylyl Group, o-tolyl group, m_tolyl group, p-tolyl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, xylyl
  • Aromatic hydrocarbon group methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, acetoxy group, benzoyloxy group
  • ester group primary amino group or methylamino group, dimethylamino group, ethylamino group, ethylamino group, propylamino group, dipropylamino group, isopropylamino group, diisopropylamino group, butylamino group, dibutylamino group, anily Substituted or unsubstituted aliphatic, alicyclic, or aromatic groups such as, o-toludino, m-toludino, p-toludino, xylidino, pyridylamino, piperazinyl, piperidino, and pyrrolidino Amino group, methylsulfamoyl group, dimethylsulfamoyl group, ethyl
  • a hydrogen atom in such a substituent may be one or more of Are plural, for example, methyl group, ethyl group, propyl group, isopropyl group
  • the azo-based organometallic complex represented by the general formula 1 is obtained by bonding one or more azo compounds, which are the same or different from each other, to a metal atom M serving as a central atom as a ligand. is there.
  • the metal atom M is usually scandium, yttrium, titanium, zirconium, hafnium, vanadium, niobium, tantalum, chromium, molybdenum, tungsten, manganese, technetium, rhenium, iron, ruthenium, osmium, cobalt, orifice,
  • Metal elements of Groups 3 to 12 in the periodic table such as iridium, nickel, palladium, platinum, copper, silver, gold, zinc, cadmium, and mercury, are employed.
  • Cobalt or nickel is usually used because it is easily available and easy to handle.
  • a and A ′ in the general formula 1 can form a coordinate bond by donating an electron pair to a metal atom, for example, in a periodic table such as an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom. Same as each other selected from the elements of Group 16 Or different heteroatoms.
  • L + represents an appropriate counter ion, and is usually, for example, an inorganic cation such as sodium ion, potassium ion, or calcium ion, or an organic cation such as ammonium ion, alkyl ammonium ion, or pyridinium ion. Is selected from
  • azo-based organometallic complexes include, for example, those represented by Chemical Formulas 1 to 7. All of these have remarkable properties to improve the light resistance of styryl dyes to the visible region, more specifically, to ambient light of a wavelength of 350 to 850 nm, and have compatibility with styryl dyes. It is extremely useful in practicing the present invention since it does not substantially impair the solubility of the styryl dye in an organic solvent.
  • all of the azo-based organometallic complexes represented by Chemical Formulas 1 to 7 are azo-compounds constituting the azo-based organometallic complex represented by General Formula 1 in a conventional manner.
  • the desired amount can be obtained by reacting a heterocyclic compound such as an acid compound, a hydantoin compound, and a rhodanine compound.
  • the lightfastness improving agent referred to in the present invention means a general optical functional material which essentially contains one or more of such azo-based organometallic complexes and whose purpose is to improve the lightfastness of styryl dyes.
  • the styryl dye to which the light resistance improver is applied will be described.
  • the styryl dye referred to in the present invention is a dimethine chain in which a heteroaromatic ring is bonded to one end and an aromatic ring or a heteroaromatic ring is bonded to the other end.
  • an organic dye compound represented by the general formula 2 is used.
  • the compound represented by the general formula 2 is preferable.
  • Z 5 represents a heteroaromatic ring, and the heteroaromatic ring may have one or more substituents.
  • Y in Z 5 is, for example, ChissoHara Represents a heteroatom selected from elements of Group 15 or 16 in the Periodic Table such as atoms, oxygen atoms, sulfur atoms, selenium atoms, and tellurium atoms, and represents a counter ion X-- and an onium salt described below.
  • Z 6 represents an aromatic ring or a heteroaromatic ring, and the aromatic ring and the heteroaromatic ring may have one or more substituents.
  • heteroaromatic ring in Z 5 and Z 6 examples include, for example, an imidazole ring, a benzimidazole ring, a quinoxalizimidazole ring, an indolenine ring, an ⁇ -naphthoindolenin ring,) 3—naphthwearnine ring, oxazole Ring, benzoxazole ring, naphthoxazole ring, ⁇ -naphthoxazole ring, oxazoline ring, quinoline ring, benzoselenazole ring, thiazole ring, benzothiazole ring, ⁇ _naphthothiazole ring, / 3- naphthoquinone Tochiazoru ring, thiazol down ring, pyran ring, Chiopiran ring, benzopyran ring, a pyridine ring, pyrrolidine ring, etc., and as the contact Ker
  • the substituent in Zeta 5 and Z s for example, Furuoro group, black port group, bromo group, a halogen group such as Yodo group, a methyl group, Echiru group, propyl group, isopropyl group, 1 one propenyl group, 2 —propenyl, 2 —vinyl, butyl, isobutyl, sec —butyl, tert —butyl, 2 —butenyl, 1,3 —butenyl, pentyl, isopentyl, Aliphatic hydrocarbon groups such as neopentyl, tert-pentyl, 1-methylpentyl, 2-methylpentyl, 2-pentenyl, 2-penten-4-yl, hexyl, and isohexyl , Methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, phenoxy, benzyloxy,
  • Alkylsulfonyl groups such as propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, methylsulfamoyl group, dimethylsulfamoyl group, ethylsulfamoyl group, getylsulfamoyl group, propylsulfamoyl group, dipropylsulfamoyl Groups, an alkylsulfamoyl group such as a butylsulfamoyl group and a dibutylsulfamoyl group, and a hydroxy group, a carboxy group, a sulfo group, a nitro group, a cyano group, and the like.
  • one or more of the hydrogen atoms may be, for example, a halogen group such as a fluoro group, a chloro group, a bromo group, a sulfide group, a methoxy group, an ethoxy group, a propoxy group, Ether groups such as isopropoxy, butoxy, tert-butoxy, and phenoxy groups, phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, mesityl, o-cumenyl, m —It may be replaced by an aromatic hydrocarbon group such as a cumenyl group, p_cumenyl group, biphenylyl group and the like.
  • the substituent in Z 4 is are bound together substituent What happened adjacent, for example, may form a Mechirenjiokishi group, cyclic ether group comprising a like Echirenjiokishi
  • R in the general formula 2 represents an aliphatic hydrocarbon group.
  • Each aliphatic hydrocarbon group usually has up to 12 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a isopropyl group, an isopropyl group.
  • One or more of the hydrogen atoms in such an aliphatic hydrocarbon group may be, for example, a halogen group such as a fluoro group, a chloro group, a bromo group, an aldehyde group, a methyl group, an ethyl group, a propyl group, or an isopropyl group.
  • a halogen group such as a fluoro group, a chloro group, a bromo group, an aldehyde group, a methyl group, an ethyl group, a propyl group, or an isopropyl group.
  • Aliphatic hydrocarbon groups such as butyl, isobutyl, sec-butyl, and tert-butyl groups; alicyclic hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; phenyl Group, o — tolyl group, m _ tolyl group, p — tolyl group, xylyl group, mesityl group, o — cumenyl group, m-cumenyl group, p-cumenyl group, biphenylyl group, etc.
  • R 2 in the general formula 2 represents a hydrogen atom or an appropriate substituent.
  • substituent in R 2 include an aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group.
  • substituents include an ether group such as a tert-butoxy group, a halogen group such as a fluoro group, a chloro group, a bromo group and an odo group, a cyano group, a nitro group, and the like. And one or more of them may be substituted by an octalogen group such as, for example, a fluoro group, a chloro group, a bromo group, and an iodo group.
  • R 2 is an aliphatic hydrocarbon group or an ether group
  • the aliphatic hydrocarbon group and the ether group are bonded to the carbon atom constituting Z 5 to form a ring such as a cyclohexene ring. May form a structure.
  • X in the general formula 2 represents an appropriate counter ion.
  • the counter ion may be appropriately determined in consideration of the solubility of the styryl dye in each organic solvent and the stability in the glassy state, and is usually a fluoride ion, a chloride ion, a bromine ion, or the like.
  • Inorganic acid anions such as thiocyanate ion, benzenesulfonic acid ion, naphthalenesulfonic acid ion, naphthalene disulfonic acid ion, p_toluenesulfonic acid ion, alkylsulfonic acid ion, benzenecarboxylic acid ion, alkylcarboxylic acid Ion, trihaloalkyl carboxylate ion, alkyl sulfate ion, Organic acid anions such as kill sulfate ion and nicotinate ion,
  • styryl dyes include, for example, Chemical Formulas 8 to 18 are mentioned. In addition, any of these can be obtained in a desired amount according to a known method.
  • Chemical formula 13 Chemical formula 14: Chemical Formula 15:
  • the light absorber according to the present invention comprises one or more styryl dyes as described above and one or more azo organometallic complexes as a lightfastness improver.
  • the azo-based organometallic complex is capable of preventing the styryl dye from deteriorating, fading, discoloring, and discoloring due to exposure to ambient light such as artificial light and natural light without substantially impairing the light absorption characteristics of the styryl dye.
  • the light absorber of the present invention is extremely useful as a material constituting a recording layer of an organic optical recording medium such as DVD-R. Although it depends on the application, for example, when used for a high-density optical recording medium such as DVD-R, 0.01 parts by weight or more of the azo-based organometallic complex is used for 1 part by weight of the styryl dye.
  • the amount of the azo-based organometallic complex is less than 0.01 part by weight, the light resistance of the styryl dye is not improved to the expected level, while 0.5 part by weight is not improved. If the amount exceeds the above range, the electrical characteristics of the optical recording medium are remarkably deteriorated. Therefore, the amount is usually adjusted within the range of 0.05 to 0.5 part by weight, preferably 0.1 to 0.4 part by weight.
  • the azo-based organometallic complex is used in advance, even if it is previously mixed with the styryl dye, it is separated from the styryl dye and added to the target. It may be adjusted so that
  • the light absorber according to the present invention When used in an optical recording medium, the light absorber of the present invention does not require any special treatment or operation. Therefore, the optical recording according to the present invention
  • the medium can be manufactured according to a conventionally known optical recording medium.
  • the light absorbing agent according to the present invention may contain one or more other organic dye compounds that substantially absorb visible light, if necessary, in order to adjust the light reflectance and light absorption in the recording layer.
  • an ultraviolet curable resin or thermosetting resin containing a flame retardant, stabilizer, antistatic agent, etc. is applied, and the protective layer that adheres to the reflective layer by being irradiated with light or heated and cured. Form. Thereafter, if necessary, a pair of substrates on which the recording layer, the reflective layer, and the protective layer are formed as described above are attached to each other with the protective layers facing each other with, for example, an adhesive or an adhesive sheet, or A protective plate having the same material and shape as that of the substrate is attached to the protective layer.
  • the method for forming the recording layer should not be limited to the method of applying the light absorbing agent of the present invention in a solution, and the method of sublimation is not limited thereto. For example, a vacuum evaporation method, A thin film of the light absorbing agent may be formed directly on the substrate by a method such as a chemical vapor deposition method or an atomic layer epitaxy method.
  • organic dye compound used in combination with the styryl dye in the present invention substantially absorbs visible light and reflects light from an optical recording medium.
  • an organic dye compound may have a substituent at both ends of a polymethine chain such as a monomethine chain or a dimethine chain, a trimethine chain, a tetramethine chain, a pentamethine chain, a hexamethine chain, and a heptamethine chain which may have one or more substituents.
  • Imidazoline ring imidazole ring, imidazole ring, benzimidazole ring, 1-naph-to-imidazole ring, ⁇ -naph-to-imidazole ring, indole ring, isoindole ring, indolenine ring, isoindone Renin ring, benzoindolenine ring, pyridinoindolenine ring, oxazoline ring, oxazole ring, isoxazole ring, benzoxazole ring, pyridinoxazole ring, ⁇ -naphthoxazole ring, / 3-naphthoxazole ring, selenazoline ring , Serenazo Ring, benzoselenazole ring, naphthoselenazole ring, 3-naphthoselenazole ring, thiazoline ring, thiazole
  • the light absorbing agent of the present invention containing a styryl dye and an azo-based organometallic complex has extremely high light resistance. There is no need to add a lightfastness improver as an indispensable element.
  • the optical recording medium according to the present invention does not exclude an aspect in which another light resistance improving agent is appropriately used in combination, and a general-purpose nitroso compound, a tetracyanoquinodimethane compound, a dimonium compound, a metal, and the like can be used without departing from the object of the invention.
  • a complex or the like can be appropriately used in combination.
  • the styryl dye and the azo-based organometallic complex used in the present invention both exhibit solubility that does not hinder practical use in various kinds of organic solvents. Since it has excellent amorphous properties in a state, there is no particular limitation on the organic solvent for applying the light absorbing agent to the substrate.
  • the production of the optical recording medium according to the present invention is for example, TFP, which is frequently used in the production of optical recording media, or hexane, cyclohexane, methylcyclohexane, dimethylcyclohexane, ethylcyclohexane, isopropylcyclohexane, tert-butylcyclohexane , Octane, cyclooctane, benzene, toluene, xylene and other hydrocarbons, carbon tetrachloride, chloroform, 1,2-dichloroethane, 1,2-dibromoethane, trichloroethylene, tetrachlorethylene, cyclobenzene, Bromobenzene, halides such as ⁇ -dichlorobenzene, methanol, ethanol, 2,2,2-trifluoroethanol, 2-methoxyethanol (methylcellulose solvent), 2-ethoxyethanol (ethyls
  • the styryl dye and the azo-based organometallic complex used in the present invention have a high solubility in an organic solvent that is easily evaporated, such as, for example, TFP methyl sorb, ethyl sorb, and diacetone alcohol.
  • an organic solvent that is easily evaporated such as, for example, TFP methyl sorb, ethyl sorb, and diacetone alcohol.
  • crystals of styryl dye or azo-based organometallic complex do not appear, and the thickness and surface of the recording layer do not become uneven.
  • styryl dyes and azo-based organometallic complexes used in the present invention are non-halogen solvents, for example, cellosolves such as methylacetosolve and ethylacetosolve, alcohols such as diacetone alcohol, and the like. Has good solubility in ketones such as ethyl methyl ketone and cyclohexanone.
  • cellosolves such as methylacetosolve and ethylacetosolve
  • alcohols such as diacetone alcohol, and the like.
  • ketones such as ethyl methyl ketone and cyclohexanone.
  • the substrate may be a general-purpose substrate.
  • an appropriate material such as an extrusion molding method, an injection molding method, an extrusion injection molding method, a photopolymer method (2P method), a thermosetting integrated molding method, a light curing integrated molding method, or the like is used.
  • it is formed into a disk having a diameter of 12 cm and a thickness of 0.1 to 1.2 mm, and is used as a single plate, or is appropriately attached with an adhesive sheet, an adhesive, or the like.
  • the substrate material is substantially transparent and has a wavelength of 400 to 800 nm. In principle, any material can be used as long as it has a light transmittance of 80% or more, preferably 90% or more.
  • Individual materials include, for example, glass, ceramic, polymethyl methacrylate, polycarbonate, polystyrene (styrene copolymer), polymethylpentene, polyester etherimide, polyether sulfone, and polyarylate.
  • the synchronization signal and the recess indicating the address of the track or sector are usually transferred to the inner circumference of the track during molding.
  • the shape of the concave portion is not particularly limited, the concave portion is formed so that the average width is in a range of 0.3 to 0.8 m and the depth is in a range of 70 to 200 nm. It is desirable to do.
  • the light absorber according to the present invention is prepared in a solution in which the concentration of the styryl dye in the organic solvent is 0.5 to 5% (w / w) while considering the viscosity, and the dried recording layer is prepared. Is uniformly applied to the substrate so that the thickness of the substrate is 10 to 1000 nm, preferably 50 to 500 nm.
  • an undercoat layer may be provided for the purpose of protecting the substrate or improving the adhesiveness, if necessary.
  • the material of the undercoat layer include ionomers, resins, and polyamides. Polymers such as resins, vinyl resins, natural resins, silicones, and liquid rubbers.
  • cellulose esters such as nitrocellulose, cellulose phosphate, cellulose sulfate, cellulose acetate, cellulose propionate, cellulose butyrate, cellulose palmitate, and cellulose acetate propionate; methyl cellulose; Such as ethyl cellulose, propyl cellulose, and butyl cellulose.
  • the high-density optical recording medium such as a DVD-R according to the present invention includes, for example, GaN-based, A1GalnP-based, GaAsP-based, a AlAs, InGaP, InGaAsP, or InGaA1P semiconductor laser, or second-harmonic such as distributed feedback or Bragg reflection Laser light with a wavelength shorter than 70 O nm by an Nd-YAG laser or the like combined with a wave generating element (SHG element), especially from 400 to 450 nm or 63 to 680 Various kinds of information can be written at high density using a laser beam of nm.
  • SHG element wave generating element
  • the optical recording medium For reading, use a laser beam of the same wavelength as that used for writing, or a wavelength slightly higher or lower than that.
  • the optical recording medium according to the present invention has a laser at the time of writing information, though it depends on the type and the mixing ratio of the styryl dye and the azo-based organometallic complex used in combination.
  • the output is relatively strong above the energy threshold at which the pit is formed, while reading the written information It is desirable to set the output at that time below the threshold and relatively low
  • writing is performed in a range of more than 4 mW and not exceeding 50 mW, and reading is adjusted in a range of 0.1 to 4 mW.
  • the recorded information is read by detecting a change in the amount of reflected light or the amount of transmitted light between the pit and the portion where the pit is not formed on the recording surface of the optical recording medium by optical pickup.
  • an optical pickup using a laser beam having a wavelength shorter than 700 nm in particular, a laser beam having a wavelength of 400 to 450 nm or 63 to 68 nm.
  • a track pitch of less than 1.6 m which is the current CD-R track pitch (typically 0.74 m)
  • a pitch length of less than 0.834 mZ (Usually 0.2 A mZ pits), and minute pits can be formed with high density and speed.
  • the recording capacity far exceeds 0.682 GB on one side, which cannot be easily achieved with the current CD-R (usually, An extremely high-density optical recording medium capable of recording moving images for about 2 hours can be realized.
  • the optical recording medium according to the present invention can record character information, image information, audio information, and other digital information at a high density, it records and stores documents, drawings, data, computer programs, and the like. It is extremely useful as a recording medium for consumer and business use.
  • Examples of the types of business and information that can use the optical recording medium according to the present invention include construction, construction in civil engineering, civil engineering drawings, maps, roads, river ledgers, apachiyua cards, architectural drawings, disaster prevention materials, and wiring. Drawings, layout drawings, newspaper / magazine information, local information, construction reports, etc., manufacturing blueprints, ingredient lists, prescriptions, product specifications, product price lists, parts lists, maintenance information, accidents.
  • optical recording medium of the present invention which can be written only once, must not be falsified or erased.
  • optical recording medium of the present invention which can be written only once, must not be falsified or erased.
  • optical recording medium examples include a compact disk, a digital video disk, a laser disk, an MD (information recording system using a magneto-optical disk), a CDV (a laser disk using a compact disk). ), DAT (information recording system using magnetic tape) System), CD-ROM (read-only memory using a compact disk), DVD_RAM (writable read memory using a digital video disk), digital photos, movies, video software, audio software, computers It can be used for editing and proofreading graphics, publications, broadcast programs, commercial messages, game software, etc., as well as for large-sized computers and as an external program recording means for car navigation.
  • the application of the light absorbing agent according to the present invention in the field of optical recording media has been mainly described for application to optical recording media using laser light having a wavelength shorter than 70 O nm as writing light.
  • the use of the light absorber according to the present invention is not limited to high-density optical recording media such as DVD-R, but also to current optical recording media such as CD-R.
  • Adjust or correct the light absorption or light reflectance of the optical recording medium by combining it with one or more other organic dye compounds that substantially absorb the laser light of 775 to 795 nm Can also be advantageously used as a material for this.
  • the optical recording medium according to the present invention means any recording medium utilizing the property that the styryl dye substantially absorbs visible light having a wavelength shorter than 700 nm.
  • organic dyeing A thermal coloring method that uses a chemical reaction between the color former and the developer due to the heat generated by the light absorption of the compound, and a phenomenon in which the periodic uneven pattern provided on the surface of the substrate is flattened by such heat generation Using the so-called “moth-eye method”
  • the light absorbing agent of the present invention containing the styryl dyes represented by Chemical Formulas 14 and 16 substantially absorbs visible light having a wavelength of around 400 nm in a thin film state. It is also useful as a material for forming a recording layer of a high-density optical recording medium using a laser beam having a wavelength of 405 nm as incident light.
  • the light absorbing agent of the present invention which substantially absorbs visible light is used, for example, for a material for polymerizing a polymerizable compound by exposing the polymerizable compound to visible light and a solar cell in addition to the use in an optical recording medium. It is useful as a material for sensitizing, a light absorbing material in an optical filter, a laser active substance in a dye laser, and a material for dyeing various kinds of clothing. Further, the light absorbing agent of the present invention may be used, if necessary, together with one or more other light absorbing agents that absorb light in the ultraviolet, visible, and / or infrared regions, as well as general clothing and other clothing.
  • Shoe insoles, shoe lining, satoshi, furoshiki, umbrellas, umbrellas, stuffed animals and lighting equipment for example, cathode ray tube displays, liquid crystal displays, electroluminescent displays Television receivers that use sprays, plasma displays, etc.—Classes for information display devices such as personal computers, panels and screens, sunglasses, sunroofs, sun visors, PET bottles , Storage, plastic greenhouses, cold gauze, optical fiber, prepaid cards, microwave ovens, ovens, etc., as well as packaging materials for packing, filling or containing these items, filling materials, containers, etc.
  • This product which has high resistance to environmental light such as natural light and artificial light, and is easy to handle, is useful as a light absorber constituting the recording layer of an optical recording medium.
  • This product has high resistance to environmental light such as natural light and artificial light, and is easy to handle. Is useful as a light absorber constituting a recording layer of an optical recording medium.
  • Example 3 Light absorber
  • the transmittance (T Q ) at a wavelength of 400 nm or 600 nm of the substrate coated with the styryl dye was measured according to the absorption maximum wavelength of the styryl dye, and then the glass substrate was moved to 500 W xenon. The lamp was exposed for 25 minutes. Immediately thereafter, the transmittance (T) at a wavelength of 400 nm or 600 nm was measured again, and these transmittances T and T were measured. Was substituted into Formula 1 to calculate the residual dye ratio (%).
  • a system was provided in which the azo-based organometallic complex was omitted for each styryl dye, and these were treated in the same manner as above to serve as controls. Table 1 summarizes the results.
  • Chemical formula 8 Chemical formula 1 540 97.6 Present invention Chemical formula 8 No addition 540 92.2 Reference Chemical formula 1 1 Chemical formula 1 600 8 9.5 Present invention Chemical formula 1 1 Chemical formula 2 600 1 0 0.0 0.0 Present invention chemical formula 1 1 Additive 600 3.2 Control Chemical Formula 1 2 Chemical Formula 1 586 9 0.8 Present Chemical Formula 1 2 Additive 586 1.0 Control Chemical Formula 1 3 Chemical Formula 2 598 9 2.6 Present Chemical Formula 1 3 Chemical Formula 5 598 7 6.7 Chemical formula of the present invention 1 3 Chemical formula 6 598 9 1.2 Chemical formula 13 of the present invention not added 598 54.5 Reference Chemical formula 16 6 Chemical formula 5 350 (54.5) 6) Reference Chemical formula 18 Chemical formula 2 562 (95.8) Chemical formula of the present invention 18 Chemical formula 7 562 (100.0.0) Chemical formula 18 of the present invention No additive 562 (8.1.2) Comparative Note: The numbers in parentheses indicate the residual dye ratio measured at a wavelength of 400 nm ⁇
  • the substrate (diameter: 12 cm, thickness: 0.6 mm) was evenly spin-coated on one side and dried to form a 120-nm-thick recording layer. Thereafter, silver is sputtered on the substrate to a thickness of 100 nm to form a reflective layer which is in close contact with the recording layer, and a known UV-curable resin (trade name “Dicure Clear”) is applied to the reflective layer.
  • optical recording media were prepared by attaching a protective plate (diameter 12 cm, thickness 0.6 mm). Each of the optical recording media of this example has a recording capacity of more than 4 GB and uses a laser beam having a wavelength of about 65 nm to produce a large amount of document information, image information, audio information, and other digital information. Information can be written at high density.
  • An optical recording medium was produced in the same manner as in Example 6, except that the light absorber prepared by the method of Example 4 was used and the substrate and the protective plate were changed to those made of acryl resin.
  • the optical recording medium of this example has a recording capacity of more than 15 GB and uses a laser beam having a wavelength of around 400 nm to enhance a large amount of document information, image information, audio information, and other digital information. Can write to density
  • the present invention is based on the discovery of a novel use of an azo-based organometallic complex.
  • the lightfastness improver of the present invention containing an azo-based organometallic complex can improve lightfastness without substantially impairing the light absorption characteristics of styryl dyes, and can be used for reading light and natural light. It has the benefit of effectively suppressing unwanted changes such as degradation, fading, discoloration and denaturation of styryl dyes due to exposure to ambient light.
  • the lightfastness improver of the present invention has a wide variety of uses in various fields, such as optical recording media, photochemical polymerization, solar cells, optical filters, and dyeing, where styryl dyes are used.
  • styryl dyes are used.
  • azo-based organometallic complexes have excellent compatibility with styryl dyes in organic solvents and excellent amorphous properties in the thin film state. It has the benefit of improving the yield of the work and the application of the coating to the substrate.
  • a styryl dye as a light absorber, information is written by a single laser beam having a wavelength shorter than 100 nm.
  • the optical recording medium of the present invention writes information with a laser beam having a wavelength of 775 or 795 nm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

L"invention concerne une substance facilement utilisable, permettant d"améliorer les caractéristiques de résistance à la lumière de colorants styryliques sans nuire à leurs caractéristiques d"absorption de la lumière, ainsi que son application. Cette substance renferme un complexe organométallique azoïque contenant un atome métallique et une ou plusieurs molécules de composé azoïque liées à cet atome, un absorbeur de lumière comprenant cette substance et un colorant styrylique. Cette invention concerne également un support d"enregistrement photosensible contenant cette substance ou l"absorbeur de lumière.
PCT/JP2001/009250 2000-10-27 2001-10-22 Substance permettant d"ameliorer les caracteristiques de resistance a la lumiere WO2002034841A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2000328344 2000-10-27
JP2000-328344 2000-10-27
JP2001-126672 2001-04-24
JP2001126672A JP4743994B2 (ja) 2000-10-27 2001-04-24 耐光性改善剤

Publications (1)

Publication Number Publication Date
WO2002034841A1 true WO2002034841A1 (fr) 2002-05-02

Family

ID=26602895

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2001/009250 WO2002034841A1 (fr) 2000-10-27 2001-10-22 Substance permettant d"ameliorer les caracteristiques de resistance a la lumiere

Country Status (2)

Country Link
JP (1) JP4743994B2 (fr)
WO (1) WO2002034841A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008133009A1 (fr) * 2007-04-13 2008-11-06 Fujifilm Corporation Support d'enregistrement d'information optique, procédé d'enregistrement d'information et colorant complexe métallique azoïque
JP2008279759A (ja) * 2007-04-13 2008-11-20 Fujifilm Corp 光情報記録媒体、情報記録方法、および、アゾ金属錯体色素
US20110141872A1 (en) * 2005-04-14 2011-06-16 Hideo Ando Storage medium, reproducing method, and recording method
US20110212287A1 (en) * 2005-03-15 2011-09-01 Hideo Ando Storage medium, reproducing method, and recording method
WO2012008318A1 (fr) * 2010-07-13 2012-01-19 住友精化株式会社 Stabilisant de colorant organique, composition d'élément absorbeur de lumière contenant le stabilisant de colorant organique et un colorant organique, et élément absorbeur de lumière utilisant la composition d'élément absorbeur de lumière
CN104164230A (zh) * 2014-08-15 2014-11-26 宋宝驹 一种新型近红外有机发光材料的制备方法

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4986457B2 (ja) 2005-04-05 2012-07-25 株式会社Ａｄｅｋａ シアニン化合物、光学フィルター及び光学記録材料
JP4884800B2 (ja) * 2006-02-28 2012-02-29 富士フイルム株式会社 光情報記録媒体及び金属錯体化合物
JP4979248B2 (ja) 2006-03-14 2012-07-18 株式会社Ａｄｅｋａ 光学記録媒体
CN101415780B (zh) 2006-03-31 2013-06-12 株式会社艾迪科 吲哚鎓化合物以及光学记录材料
KR20080114742A (ko) 2006-03-31 2008-12-31 가부시키가이샤 아데카 시아닌 화합물 및 광학기록재료
JP5102202B2 (ja) 2006-04-28 2012-12-19 株式会社Ａｄｅｋａ 光学記録材料、カルコン型化合物及び金属錯体
JP5078386B2 (ja) 2006-05-08 2012-11-21 株式会社Ａｄｅｋａ 新規化合物、該化合物を用いた光学フィルター及び光学記録材料
JP5107239B2 (ja) 2006-05-23 2012-12-26 株式会社Ａｄｅｋａ 光学記録材料及びシアニン化合物
JP5241084B2 (ja) 2006-07-21 2013-07-17 株式会社Ａｄｅｋａ 架橋型シアニン化合物及び該化合物を用いた光学記録材料
CN101516633B (zh) 2006-10-10 2012-07-04 株式会社艾迪科 光学记录材料
JP5475244B2 (ja) 2007-03-30 2014-04-16 株式会社Ａｄｅｋａ シアニン化合物、該化合物を用いた光学フィルター及び光学記録材料
JP5086026B2 (ja) 2007-10-15 2012-11-28 株式会社Ａｄｅｋａ インドリウム化合物及び該化合物を用いた光学記録材料
JP5913776B2 (ja) 2008-05-27 2016-04-27 株式会社Adeka 色補正材料、フィルム形成用組成物及び光学フィルター
JP5551089B2 (ja) 2008-12-25 2014-07-16 株式会社Ａｄｅｋａ シアニン化合物を用いた近赤外線吸収材料及びシアニン化合物
JP4982536B2 (ja) * 2009-08-10 2012-07-25 株式会社東芝 情報記憶媒体、再生方法、再生装置、記録方法、記録装置及び材料
JP4810599B2 (ja) * 2009-08-10 2011-11-09 株式会社東芝 情報記憶媒体、再生方法及び記録方法
EP2677364A4 (fr) 2011-02-18 2015-05-13 Adeka Corp Composition colorante photosensible
JP2012208465A (ja) 2011-03-16 2012-10-25 Adeka Corp 光拡散性樹脂組成物及びこれを用いた光拡散シート

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6381165A (ja) * 1986-09-24 1988-04-12 Mitsubishi Kasei Corp クロム含金アゾ系化合物及び同化合物を含む光学記録媒体
EP0621317A1 (fr) * 1993-04-21 1994-10-26 MITSUI TOATSU CHEMICALS, Inc. Composé azoique et film polarisant le contenant
EP1130063A1 (fr) * 1999-09-14 2001-09-05 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Colorant de styryle

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09323478A (ja) * 1996-06-06 1997-12-16 Tdk Corp 光記録媒体
JP4754698B2 (ja) * 2000-02-10 2011-08-24 株式会社林原生物化学研究所 シアニン色素
JP2002206061A (ja) * 2000-07-05 2002-07-26 Hayashibara Biochem Lab Inc スチリル色素
JP2002074740A (ja) * 2000-08-25 2002-03-15 Hayashibara Biochem Lab Inc 光記録媒体
JP2002283732A (ja) * 2001-03-26 2002-10-03 Ricoh Co Ltd 光記録媒体及び光記録方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6381165A (ja) * 1986-09-24 1988-04-12 Mitsubishi Kasei Corp クロム含金アゾ系化合物及び同化合物を含む光学記録媒体
EP0621317A1 (fr) * 1993-04-21 1994-10-26 MITSUI TOATSU CHEMICALS, Inc. Composé azoique et film polarisant le contenant
EP1130063A1 (fr) * 1999-09-14 2001-09-05 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Colorant de styryle

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110212287A1 (en) * 2005-03-15 2011-09-01 Hideo Ando Storage medium, reproducing method, and recording method
US20110141872A1 (en) * 2005-04-14 2011-06-16 Hideo Ando Storage medium, reproducing method, and recording method
WO2008133009A1 (fr) * 2007-04-13 2008-11-06 Fujifilm Corporation Support d'enregistrement d'information optique, procédé d'enregistrement d'information et colorant complexe métallique azoïque
JP2008279759A (ja) * 2007-04-13 2008-11-20 Fujifilm Corp 光情報記録媒体、情報記録方法、および、アゾ金属錯体色素
WO2012008318A1 (fr) * 2010-07-13 2012-01-19 住友精化株式会社 Stabilisant de colorant organique, composition d'élément absorbeur de lumière contenant le stabilisant de colorant organique et un colorant organique, et élément absorbeur de lumière utilisant la composition d'élément absorbeur de lumière
JP5687274B2 (ja) * 2010-07-13 2015-03-18 住友精化株式会社 有機色素安定化剤、該有機色素安定化剤と有機色素を含有する光吸収部材用組成物、およびこれを用いた光吸収部材
CN104164230A (zh) * 2014-08-15 2014-11-26 宋宝驹 一种新型近红外有机发光材料的制备方法

Also Published As

Publication number Publication date
JP4743994B2 (ja) 2011-08-10
JP2002201373A (ja) 2002-07-19

Similar Documents

Publication Publication Date Title
JP4743994B2 (ja) 耐光性改善剤
JP5320411B2 (ja) スチリル色素
JP4702731B2 (ja) シアニン色素
JP2002206061A (ja) スチリル色素
EP1191526B1 (fr) Supports d'enregistrement optiques
KR20010082123A (ko) 시아닌색소
JP2011052218A (ja) シアニン色素
CN101437902B (zh) 次甲基类染料及其用途
JP4702730B2 (ja) スチリル色素
JP4173735B2 (ja) 光吸収剤
JP4666869B2 (ja) シアニン色素
JP4666742B2 (ja) 光吸収材とその用途
WO2000075111A1 (fr) Complexe metallique de formazan
JP4754698B2 (ja) シアニン色素
JP3232512B2 (ja) シアニン色素
JP2001323179A (ja) シアニン色素
JP3834053B2 (ja) 光記録媒体
JP2001348500A (ja) シアニン色素

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载