JP2001023235A - Optical recording medium - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a material for DVD-R, which is excellent in light resistance and preservation stability applicable to a high density optical disk utilizing a semiconductor laser having a short wavelength by incorporating at least one kind of formazan metal dyestuff into a recording medium having a recording layer, a reflection layer, a protective layer or an adhesive layer and a second substrate provided on a substrate. SOLUTION: This is an optical recording medium containing a formazan metal dyestuff shown by the formula. Thereby, the recording medium capable of recording and reproducing utilizing a beam having 630-680 nm wavelength is obtained. When the formazan metal dyestuff is used as a light stabilizer, it is preferably used being mixed with a dyestuff having the maximum absorption wavelength in the rage of 550-630 nm. In the formula, Z denotes a residual group which is bonded to C and N to form a polyheterocyclic ring; A denotes an alkyl, aryl-alkyl, aryl or cyclohexyl group; B denotes an aryl group; M denotes a bivalent metal atom; and n denotes the number of the formazan ligands coordinated to the M. Z is preferably a pyridazine, pryimidine, pyrazine or triazine ring and M is preferably Fe, Co, Ni, Cu, Zn or Pd.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention generally relates to an information recording medium, and more particularly, to irradiating a light beam to cause an optical change such as the transmittance and the reflectance of a recording material. An information recording medium on which information can be recorded, reproduced, and additionally recordable, such as a recordable optical disc for data,
It relates to a write-once compact disc (DVD-R).

[0002]

2. Description of the Related Art As a conventional technology for DVD-R recording materials,
A recording material using a polymethine dye is disclosed in
3577, JP-A-10-119434, JP-A-10-149584, and JP-A-10-1883
JP-A-10-109475, JP-A-10-109475 and JP-A-10-109475 disclose recording materials using a polymethine dye and a light stabilizer as a recording material.
-109476, JP-A-10-134413, JP-A-10-151861, JP-A-10-1
No. 66739, which uses an azo metal chelate dye as a recording material, is disclosed in JP-A-8-295811, JP-A-8-295812, and JP-A-9-33.
No. 2772, JP-A-9-39394, JP-A-10-6650, JP-A-10-58828, JP-A-10-157293, JP-A-10-1
No. 57300, JP-A-10-188340,
JP-A-10-188341, which are described in JP-A-8-169182, JP-A-8-209012, and JP-A-9-58130, use other dyes and a metal reflective layer as a recording material. It is described in the gazette,
JP-A-8-295079 and JP-A-9-193546 use recording materials containing a formazan metal chelate dye.
JP, JP-A-10-152623, JP-A-10-152623
-154350.

At present, as a next-generation large-capacity optical disk, DV
Development of DR is in progress. Elemental technologies for improving the recording capacity include recording material development for miniaturizing recording pits, MP
It is necessary to develop an image compression technique represented by EG2 and to shorten the wavelength of a semiconductor laser for reading recorded pits. Heretofore, as a semiconductor laser in the red wavelength range, a 670 nm band AlGa has been used for bar code readers and measuring instruments.
Although only InP laser diodes have been commercialized, red lasers are being used in the optical storage market in earnest as the density of optical disks increases. In the case of a DVD drive, the light source is standardized at two wavelengths, a 635 nm band and a 650 nm band laser diode. For high-density recording, it is desirable that the wavelength be shorter,
A wavelength of 635 nm is preferable for a drive for a write-once medium. On the other hand, a read-only DVD-ROM drive is commercialized at a wavelength of 650 nm.

[0004] Under these circumstances, the most preferable DVD-
The R medium is a medium (DV) capable of recording and reproducing at a wavelength of 635 nm and reproducing at a wavelength of 650 nm.
There is a demand for a recording material which has excellent light resistance and storage stability and can be recorded and reproduced by an optical pickup using a laser of 650 nm or less. Recently, polymethine dyes and azo metal chelate dyes have been actively developed as recording materials.

[0005] Among polymethine dyes, in particular, cyanine dyes and squarylium dyes are excellent in optical properties and can provide satisfactory signal characteristics, but have extremely poor light fastness and cannot be put to practical use by themselves. As an improvement,
Light stabilizers are being developed, but none have yet been found that have both light stabilizing ability and signal characteristics. The azo metal chelate dye also has satisfactory signal characteristics, but does not have sufficient light fastness.

On the other hand, formazan metal chelate dyes are known to have extremely high light stability, and have been tried to be applied as optical recording materials.
It was not suitable as a recording material for DR. Attempts have also been made to apply cyanine dyes as light stabilizers.However, the light stabilization mechanism is based on the transfer of excitation energy from the main dye to the light stabilizer, so more efficient light stabilizers are mainly used. It is necessary to have absorption capability at an energy level closer to the excitation energy of the dye. In this sense, the conventional formazan metal dye has an absorption wavelength that is too long, and has not been able to exhibit sufficient light stabilizing ability.

[0007]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a high solubility in an organic solvent applicable to a high-density optical disk system using a semiconductor laser having an oscillation wavelength in a short wavelength, as compared with the above conventional system. Light fastness,
An object of the present invention is to provide a recording material for DVD-R having excellent storage stability. Another object of the present invention is to provide a light stabilizer for improving the light stability of a polymethine dye, a squarylium dye, and an azo metal dye exhibiting excellent signal characteristics as a recording dye for DVD-R.

[0008]

As a result of investigations by the present inventors, the present inventors have found that a recording layer mainly composed of a formazan metal dye having a specific structure has the above-mentioned characteristics, and have developed a semiconductor laser having an oscillation wavelength of 700 nm or less. An optical recording medium that is applicable to the high-density optical disk system used and has high light resistance has been reached. That is, the present invention provides (1) a light-emitting device comprising: a recording layer provided directly or via an undercoat layer on a substrate, and a reflective layer, a protective layer or an adhesive layer, and a second substrate provided thereon if necessary. An optical recording medium comprising at least one compound represented by the following general formula (I).

[0009]

Embedded image Wherein Z represents a residue which, together with the carbon and nitrogen atoms to which it is attached, forms a polyheterocycle;
The polyheterocycle may have a substituent such as an alkyl group, an alkoxy group, a thioalkoxy group, a substituted amino group, an allyl group, an allyloxy group, an anilino group, and a keto group. A is
Represents an alkyl group, an aralkyl group, an allyl group, a cyclohexyl group, an alkyl group, an alkoxy group, a halogen group,
It may have a substituent such as a keto group, a carboxyl group or an ester thereof, a nitrile group, a nitro group and the like. B represents an allyl group, an alkyl group, an alkoxy group, a halogen group, a carboxyl group or an ester thereof, a nitrile group,
It may have a substituent such as a nitro group. M represents a divalent metal atom. n represents the number of formazan ligands coordinated to M. ) ", (2)" in the general formula (I),
The optical recording medium according to the above (1), wherein Z is a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring. ", (3)" in the general formula (I), M is iron, cobalt, nickel, copper, zinc or palladium, the above (1) or (2). (4) The optical recording medium, wherein the recording layer comprises a mixed layer of a light absorbing dye having a maximum absorption wavelength of 550 to 630 nm in addition to the general formula (I). (5) The optical recording medium according to any one of (3) to (3), wherein the recording layer has a maximum absorption wavelength of the compound of the formula (I) which is the maximum of the light absorbing dye. The optical recording medium according to the above (4), comprising a mixed layer configured to have an absorption wavelength longer than −50 nm. ”, (6)“ where the light absorbing dye is a polymethine dye (4) is a squarylium dye or an azo metal chelate dye, Wherein said (5) The optical recording medium according to claim. ", And (7)" The optical recording medium according to claim (6), characterized in that the said polymethine dye is a cyanine dye. ".

Here, the above item (1) is a basic structure and a material constitution as a high-density optical recording medium using the formazan metal chelate dye of the present invention, and the above items (2) and (3) The term is an optimum chemical structure of the general formula (I) for obtaining the good optical recording medium of the above item (1). No. (4)
Item is a basic material configuration using the formazan metal dye of the present invention as a light stabilizer, item (5) is a basic structure using the most efficient light stabilizer, and item (6) is the item (4). Item is an optimum constituent material for obtaining the good optical recording medium of the above item (5), and item (7) is an optimum constituent material of the polymethine dye of the above item (6).

As an optical recording medium having a reflective layer on a substrate, a recordable CD (CD-R) conforming to the compact disk (CD) standard has been commercialized. Wavelength 7 on recording layer
Information is recorded and reproduced by irradiating a laser beam of 70 to 830 nm and detecting reflected light that causes a physical or chemical change in the recording layer. Recently, semiconductor lasers having shorter wavelengths have been developed, and red semiconductor lasers having wavelengths of 630 to 680 nm have been put to practical use. It is possible to make the beam diameter smaller by shortening the wavelength of the recording / reproducing laser,
A high-density optical recording medium becomes possible. The present invention provides a wavelength 63
The present invention relates to a high-density optical recording medium (DVD-R) using a recording material capable of recording and reproducing at 0 to 680 nm.

<Structure of Recording Body> The structure of the recording medium of the present invention may be a write-once optical disc (a so-called air sandwich structure in which two recording layers are provided on a substrate and bonded together). Structure (recording layer on substrate,
(Reflective layer, protective layer) or a structure in which a CD-R structure is bonded.

<Substrate> The substrate used must be transparent to the laser used only when recording / reproducing is performed from the substrate side. The substrate does not need to be transparent when recording / reproducing is performed from the recording layer side. As a substrate material, for example, plastic such as polyester, acrylic resin, polyamide, polycarbonate resin, polyolefin resin, phenol resin, epoxy resin, polyimide, glass, ceramic, or metal can be used. A guide groove for tracking, a guide pit, and a preformat such as an address signal may be formed on the surface of the substrate.

<Recording Layer> The recording layer causes some optical change by irradiation with a laser beam, and records information by the change. The recording layer has the general formula (I) of the present invention. It is necessary to contain at least one of the compounds shown.

[0015]

Embedded image Wherein Z represents a residue which, together with the carbon and nitrogen atoms to which it is attached, forms a polyheterocycle;
The polyheterocycle may have a substituent such as an alkyl group, an alkoxy group, a thioalkoxy group, a substituted amino group, an allyl group, an allyloxy group, an anilino group, and a keto group. A is
Represents an alkyl group, an aralkyl group, an allyl group, a cyclohexyl group, an alkyl group, an alkoxy group, a halogen group,
It may have a substituent such as a keto group, a carboxyl group or an ester thereof, a nitrile group, a nitro group and the like. B represents an allyl group, an alkyl group, an alkoxy group, a halogen group, a carboxyl group or an ester thereof, a nitrile group,
It may have a substituent such as a nitro group. M represents a divalent metal atom. n represents the number of formazan ligands coordinated to M. )

Specific examples of Z include thiazole, benzothiazole, oxazole, benzoxazole, pyrazole, benzopyrazole, imidazole, benzimidazole, oxadiazole, triazole, thiadiazole, and pyridazine. Ring, pyrimidine ring, pyrazine ring, triazine ring, naphthalidine ring,
Examples thereof include a fructazine ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, and a phenazine ring. In view of optical properties, storage stability, and light resistance, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring are particularly preferable.

Specific examples of B include phenyl, pentalenyl, indenyl, naphthyl, azulenyl,
Heptalenyl group, biphenylenyl group, as-indacenyl group, s-indacenyl group, acenaphthalenyl group, fluorenyl group, phenalenyl group, phenanthranyl group, anthranyl group, fluoracenyl group, acephenanthrenyl group, aceanthrylene group, triphenylenyl group, pyrenyl Group, chrysenyl group, naphthacenyl group and the like.

Specific examples of metal atoms include titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper,
Zinc, zirconium, niobium, molybdenum, technenium, ruthenium, rhodium, palladium and the like can be mentioned, but from the viewpoint of optical properties, storage stability and light stability, iron, cobalt, nickel, copper, zinc and palladium are particularly preferred.

Specific examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like. Specific examples of the alkyl group include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-nonyl. -Primary alkyl group such as decyl group, isobutyl group, isoamyl group, 2-methylbutyl group,
2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-ethylbutyl, 2-methylhexyl, 3-
Methylhexyl, 4-methylhexyl, 5-methylhexyl, 2-ethylpentyl, 3-ethylpentyl, 2-
Methylheptyl group, 3-methylheptyl group, 4-methylheptyl group, 5-methylheptyl group, 2-ethylhexyl group, 3-methylheptyl group
Ethylhexyl group, isopropyl group, sec-butyl group, 1-
Ethylpropyl group, 1-methylbutyl group, 1,2-dimethylpropyl group, 1-methylheptyl group, 1-ethylbutyl group,
3-dimethylbutyl group, 1,2-dimethylbutyl group, 1-ethyl
2-methylpropyl group, 1-methylhexyl group, 1-ethylheptyl group, 1-propylbutyl group, 1-isopropyl-2-
Methylpropyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-propyl-2-methylpropyl group, 1-methylheptyl group, 1-ethylhexyl group, 1-propylpentyl group, 1 -Isopropylpentyl group, 1-isopropyl-2-methylbutyl group, 1-isopropyl-3-methylbutyl group, 1-methyloctyl group, 1-ethylheptyl group, 1-
Secondary alkyl groups such as propylhexyl group and 1-isobutyl-3-methylbutyl group, tertiary alkyl groups such as neopentyl group, tert-butyl group, tert-hexyl group, tert-amyl group and tert-octyl group, and cyclohexyl group , 4-methylcyclohexyl group, 4-ethylcyclohexyl group, 4-tert-
Examples thereof include cycloalkyl groups such as a butylcyclohexyl group, a 4- (2-ethylhexyl) cyclohexyl group, a bornyl group, and an isobornyl group (adamantane group). Further, these primary and secondary alkyl groups may be substituted with a hydroxyl group, a halogen atom, a nitro group, a carboxy group, a cyano group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic residue, and the like. And may be substituted with the above-mentioned alkyl group via an atom such as oxygen, sulfur, or nitrogen. Examples of the alkyl group substituted via oxygen include:
A methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group, a butoxyethyl group, an ethoxyethoxyethyl group, a phenoxyethyl group, a methoxypropyl group, an ethoxypropyl group, a piperidino group, a morpholino group, etc. are substituted via sulfur. Examples of the alkyl group include a methylthioethyl group, an ethylthioethyl group, an ethylthiopropyl group, and a phenylthioethyl group.The alkyl group substituted with a nitrogen atom includes a dimethylaminoethyl group and a diethylaminoethyl group. And a diethylaminopropyl group.

Specific examples of the above aryl group include a phenyl group,
Pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, biphenylenyl group, as-indacenyl group, s-indacenyl group, acenaphthalenyl group, fluorenyl group, phenalenyl group, phenanthranyl group,
Anthranyl group, fluoracenyl group, acephenanthrenyl group, aceanthrylene group, triphenylenyl group,
Examples include a pyrenyl group, a chrysenyl group, and a naphthacenyl group. Further, these aryl groups may be substituted with a hydroxyl group, a halogen atom, a nitro group, a carboxy group, a cyano group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic residue, etc. The alkyl group may be substituted via an atom such as sulfur or nitrogen.

Specific examples of the above alkoxy group may be those in which a substituted or unsubstituted alkyl group is directly bonded to an oxygen atom, and specific examples of the alkyl group include the aforementioned specific examples. Specific examples of the above-described aryloxy group may be those in which a substituted or unsubstituted aryl group is directly bonded to an oxygen atom, and specific examples of aryl include the aforementioned specific examples.

In forming the recording layer, the dye 1 of the present invention was used.
They may be used in combination of two or more species. Further, the dye of the present invention may be used by mixing or laminating with other organic dyes, metals and metal compounds for the purpose of improving optical characteristics, recording sensitivity, signal characteristics and the like. Examples of organic dyes include polymethine dyes, naphthalocyanine dyes, phthalocyanine dyes, squarylium dyes, croconium dyes, pyrylium dyes, naphthoquinone dyes, anthraquinone dyes (indanthrene dyes), xanthene dyes, triphenylmethane dyes, azulene dyes, tetrahydro Choline dyes, phenanthrene dyes, triphenothiazine dyes, and metal complex compounds thereof are exemplified.

Examples of metals and metal compounds include In, T
e, Bi, Se, Sb, Ge, Sn, Al, Be, Te
O ₂ , SnO, As, Cd and the like can be mentioned, and each of them can be used in the form of dispersion mixing or lamination.

When used as a light stabilizer,
The dye having the maximum absorption wavelength at 50 nm to 630 nm is mixed with the dye of the present invention. In this case, the formazan dye preferably has an absorption at a wavelength longer than the maximum absorption wavelength of the dye -50 nm in terms of efficiency. When the wavelength is shorter than -50 nm, the light stabilizing ability is reduced. 550 nm
Preferred examples of the dye having an absorption maximum wavelength at 630 nm include a polymethine dye, a squarylium dye, a croconium dye, a pyrylium dye, a naphthoquinone dye, an anthraquinone dye (indanthrene-based), a xanthene dye,
There are triphenylmethane dye, tetrahydrocholine dye, phenanthrene dye, triphenothiazine dye, azo metal chelate dye, etc.
Squarylium dyes and azo metal chelate dyes are particularly preferred.

Further, various materials such as an ionomer resin, a polyamide resin, a vinyl resin, a natural polymer, silicone, a liquid rubber, or a silane coupling agent may be dispersed and mixed in the dye. ,
For the purpose of improving the properties, it may be dispersedly mixed with a stabilizer (for example, a transition metal complex), a dispersant, a flame retardant, a lubricant, an antistatic agent, a surfactant, a plasticizer, and the like.

The recording layer can be formed by ordinary means such as vapor deposition, sputtering, CVD or solvent coating. When the coating method is used, the above-mentioned dye or the like is dissolved in an organic solvent, and the coating can be performed by a conventional coating method such as spraying, roller coating, dipping and spin coating. As the organic solvent used, generally, methanol, ethanol, alcohols such as isopropanol, acetone,
Ketones such as methyl ethyl ketone and cyclohexanone; amides such as N, N-dimethylformamide and N, N-dimethylacetamide; sulfoxides such as dimethyl sulfoxide; ethers such as tetrahydrofuran, dioxane, diethyl ether and ethylene glycol monomethyl ether; Esters such as methyl and ethyl acetate; aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethane, carbon tetrachloride, and trichloroethane; aromatics such as benzene, xylene, monochlorobenzene, and dichlorobenzene; methoxyethanol and ethoxy Examples include cellosolves such as ethanol, and hydrocarbons such as hexane, pentane, cyclohexane, and methylcyclohexane. The thickness of the recording layer is 100 to 10 μm, preferably 200 to 20 μm.
00 is appropriate.

<Undercoat layer> The undercoat layer improves the adhesiveness,
Barrier for water or gas, improvement of storage stability of recording layer, improvement of reflectance, protection of substrate from solvent,
It is used for the purpose of forming guide grooves, guide pits, preformats, and the like. For the purpose of polymer materials,
For example, various polymer compounds such as ionomer resins, polyamide resins, vinyl resins, natural resins, natural polymers, silicones, and liquid rubbers, and silane coupling agents can be used. Inorganic compounds other than polymer materials, for example, SiO, Mg
F, SiO ₂ , TiO, ZnO, TiN, SiN and the like, and further, a metal or a semi-metal such as Zn, Cu,
Ni, Cr, Ge, Se, Au, Ag, Al and the like can be used. For the purpose of the present invention, metals such as Al, Au, Ag and the like, and organic thin films having metallic luster such as methine dyes and xanthene dyes can be mentioned. Cured resin, thermosetting resin, thermoplastic resin, or the like can be used. The thickness of the undercoat layer is 0.01 to 30 μm, preferably 0.05 to 10 μm.

<Metal Reflective Layer> The metal reflective layer can be made of a metal, a semi-metal, or the like, which can provide a high reflectance by itself, and is made of Au, Ag, Cr, Ni, Al, or F.
e, Sn, etc., but Au, Ag, and Al are most preferable from the viewpoint of reflectance and productivity. These metals and metalloids may be used alone or as two kinds of alloys.
Examples of the film forming method include vapor deposition and sputtering, and the film thickness is 50 to 5000５０, preferably 100 to
3000 $.

<Protective Layer, Hard Coat Layer on Substrate Surface> The protective layer and the hard coat layer on the substrate surface protect the recording layer (reflection / absorption layer) from scratches, dust, dirt, and the like. It is used for the purpose of improving the properties and the reflectance. For these purposes, the materials shown in the undercoat layer can be used. Further, as the inorganic material, SiO, SiO ₂ or the like can be used, and as the organic material, polymethyl acrylate, polycarbonate, epoxy resin, polystyrene, polyester resin,
Thermal softening properties of vinyl resin, cellulose, aliphatic hydrocarbon resin, natural rubber, styrene butadiene resin, chloroprene rubber, wax, alkyd resin, drying oil, rosin,
Hot-melt resins can also be used. The most preferable example of the above materials is an ultraviolet curable resin having excellent productivity. The thickness of the protective layer or the hard coat layer on the substrate surface is 0.
A suitable range is from 01 to 30 μm, preferably from 0.05 to 10 μm. In the present invention, the undercoat layer, the protective layer, and the substrate surface hard coat layer, as in the case of the recording layer,
A stabilizer, a dispersant, a flame retardant, a lubricant, an antistatic agent, a surfactant, a plasticizer and the like can be contained.

Table 1 shows examples of the compounds.

[0031]

[Table 1-1]

[0032]

[Table 1-2]

[0033]

[Table 1-3]

[0034]

[Table 1-4]

[0035]

[Table 1-5]

[0036]

The present invention will be described below in detail with reference to examples. [Example 1] A depth of 1600 °, a half-value width of 0.30 µm, and a track pitch of 0.8 µm with a guide groove of 0.8 µm
Compound Example N on an injection molded polycarbonate substrate
o.15 in a tetrafluoropropanol solution was applied by spinner to form an organic dye layer having a thickness of 700 .ANG., then a reflective layer of 2000 .ANG. of gold was provided by sputtering, and an acrylic photopolymer was further formed thereon. A protective layer having a thickness of 10 μm was provided on the recording medium.

[Examples 2, 3, 4, 5, 6, 7, 8] In Example 1, Compound No. 15 was used instead of Compound No. 15, respectively. Using 9, 11, 12, 18, 24, 32, and 40, a recording medium was obtained in exactly the same manner as in Example 6.

[Comparative Examples 1 and 2] A recording medium was prepared by using the following compounds (ratio-1) and (ratio-2) instead of Compound Example No. 8 as the organic thin film in Example 1.

[0039]

Embedded image

[0040]

Embedded image

<Recording conditions> The recording medium has an oscillation wavelength of 635.
while tracking using a semiconductor laser beam of
FM signal (linear velocity 3.0 m / sec, shortest mark length 0.4
μm) was recorded and reproduced with continuous light (reproduction power 0.7 mW) of a semiconductor laser having an oscillation wavelength of 650 nm.
N was measured. Light fastness test: Tungsten lamp, 50,000 lux, irradiation for 20 hours

Table 2 shows the evaluation results.

[0043]

[Table 2]

Examples 9 and 10 The above compound (ratio -1) and compound No. 36 were put on a 1.2 mm thick injection-molded polycarbonate flat plate by weight ratio (10 / 1.5) and weight ratio ( The mixture of (10/3) was dissolved in tetrafluoropropanol and spinner-coated to form an organic dye layer having a thickness of 1000 °. This dye thin film is put on a tungsten lamp, 5
The sample was placed under 10,000 lux and the change in absorbance of the dye was measured.

Examples 11 and 12 Dye thin films were obtained in the same manner as in Examples 9 and 10 except that the compound (ratio-1) was used instead of the compound (ratio-1).

[Comparative Example 3] A thin film of the dye of the compound of Example 9 (ratio -1) alone.

Comparative Example 4 The compound of Example 11 (ratio-2)
Only a dye thin film.

Table 3 shows the evaluation results.

[0049]

[Table 3]

Compound No. 8, 13, 16, 19, 2,
Similarly, a remarkable light stabilizing effect was obtained in 9, 35 and 46.

[0051]

As is apparent from the detailed and specific description above, the formazan metal chelate of the present invention can be coated by coating, and has a high refractive index and a high reflectance with excellent light resistance and storage stability. And a medium with a high degree of modulation, and by mixing with a polymethine dye, a squarylium dye, and an azo metal chelate dye, a medium having excellent light fastness as compared with the case of using these alone can be provided. According to claim 1, it is possible to provide an optical information recording medium capable of high-density recording and reproduction with laser light in a wavelength range of 650 nm or less, and having excellent light resistance and storage stability. Claims 2 and 3 have the most preferable chemical structure. A better optical information recording medium can be provided. Claim 4 provides an optical information recording medium used as a light stabilizer. Claim 5 shows a basic structure that functions more efficiently as a light stabilizer, and Claim 6 shows a preferable material structure. An optical information recording medium can be provided, and a preferable material composition can be provided according to claim 7, and a more excellent optical information recording medium can be provided.

 ────────────────────────────────────────────────── ─── Continued on the front page F term (reference) 2H111 EA03 EA12 EA22 EA25 EA32 EA39 EA40 EA43 EA44 FA01 FA12 FA14 FA15 FB42 FB43 FB44 FB63 5D029 JA04 JC17

Claims (7)

[Claims] 1. An optical recording medium comprising a recording layer provided directly or via an undercoat layer on a substrate, and a reflective layer, a protective layer or an adhesive layer, and a second substrate provided thereon as required. An optical recording medium comprising at least one compound represented by the general formula (I). Embedded image Wherein Z represents a residue which, together with the carbon and nitrogen atoms to which it is attached, forms a polyheterocycle;
The polyheterocycle may have a substituent such as an alkyl group, an alkoxy group, a thioalkoxy group, a substituted amino group, an allyl group, an allyloxy group, an anilino group, and a keto group. A is
Represents an alkyl group, an aralkyl group, an allyl group, a cyclohexyl group, an alkyl group, an alkoxy group, a halogen group,
It may have a substituent such as a keto group, a carboxyl group or an ester thereof, a nitrile group, a nitro group and the like. B represents an allyl group, an alkyl group, an alkoxy group, a halogen group, a carboxyl group or an ester thereof, a nitrile group,
It may have a substituent such as a nitro group. M represents a divalent metal atom. n represents the number of formazan ligands coordinated to M. ) 2. The optical recording medium according to claim 1, wherein in the general formula (I), Z is a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring. 3. The optical recording medium according to claim 1, wherein in the general formula (I), M is iron, cobalt, nickel, copper, zinc, or palladium. 4. The recording layer according to claim 1, wherein
4. The optical recording medium according to claim 1, comprising a mixed layer with a light-absorbing dye having a maximum absorption wavelength at 50 to 630 nm. 5. The recording layer, wherein the maximum absorption wavelength of the compound of the formula (I) is less than the maximum absorption wavelength of the light absorbing dye.
The optical recording medium according to claim 4, comprising a mixed layer configured to have a wavelength longer than 50 nm. 6. The optical recording medium according to claim 4, wherein the light absorbing dye is a polymethine dye, a squarylium dye, or an azo metal chelate dye. 7. The optical recording medium according to claim 6, wherein the polymethine dye is a cyanine dye.