JP2001287466A - Optical recording medium - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coloring matter, which can be used in an optical recording medium especially suitable for a record reproduction with a short wavelength semiconductor laser. SOLUTION: This optical recording medium is formed by providing a recording layer on which information can be recorded or reproduced with laser or a substrate and which includes a carbostyrile compound represented with general formula [ I ] or a 1,8-naphthylzine, wherein X represents a nitrogen atom or C-R6, R1, R2, R3, R4, R5, R6, R7 and R8 respectively and independently represent hydrogen atoms or arbitrary substituent. Two adjacent to each other among R1 to R8 may form a ring by bonding to each other.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a write-once optical recording medium using an organic dye for a recording layer, and more particularly to a write-once optical recording medium for a blue laser.

[0002]

2. Description of the Related Art In recent years, semiconductor lasers having a short oscillation wavelength have been developed, and the wavelength of a conventionally used laser has been reduced to 78 nm.
There is a demand for an optical recording medium capable of high-density recording and reproduction using laser light having a wavelength shorter than 0 nm and 830 nm. Conventionally proposed optical recording media include magneto-optical recording media,
There are a phase change recording medium, a chalcogen oxide optical recording medium, an organic dye optical recording medium, and the like. Among these, the organic dye optical recording medium is inexpensive in cost and easy in the manufacturing process. Is considered to have an advantage.

At present, writable compact discs (CD-R) of a type in which a metal layer having a high reflectance is laminated on an organic dye layer have been mass-produced and widely known as organic dye-based optical recording media. A high-density organic dye-based optical recording medium (DVD-R) for recording with a red semiconductor laser having a shorter wavelength than the laser used for recording and reproduction of the CD-R.
R) has also been developed and put into practical use. However, as laser oscillation with shorter wavelengths becomes possible, lasers with shorter wavelengths than DVD-Rs, that is, blue semiconductor lasers (wavelengths from 350 nm to
The need for an optical recording medium capable of recording / reproducing at 30 nm) is increasing.

[0004]

Generally, an optical recording medium used as a CD-R or DVD-R has a problem that, when recording and reproducing with a short-wavelength blue semiconductor laser, the reflectivity is low and recording and reproducing cannot be performed. Have. An object of the present invention is to provide an organic dye-based optical recording medium that can be recorded and reproduced by a blue semiconductor laser.

[0005]

As a result of various studies on organic dyes having high sensitivity to a blue semiconductor laser, the present inventors have found that a carbostyril derivative or a 1,8-naphthyridine compound represented by a specific structural formula is The inventors have learned that the present invention can be used for a recording layer of an optical recording medium corresponding to a blue semiconductor laser, and have reached the present invention.

That is, the gist of the present invention is an optical recording medium in which a recording layer capable of recording and / or reproducing information by a laser is provided on a substrate, wherein the recording layer is represented by the following general formula [I]. The carbostyril compound shown or 1,8
-An optical recording medium characterized by containing a naphthyridine compound.

[0007]

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Wherein X is a nitrogen atom or C—R₆The table
You. R₁, R_Two, R_Three, R_Four, R_Five, R₆, R₇And R₈Is
Each independently represents a hydrogen atom or an arbitrary substituent.
Also R ₁~ R₈Two of the following are joined to form a ring
May be. )

[0009]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The compound of the general formula [I] used in the present invention includes:
This dye has absorption in the blue light region of 350 to 530 nm and is suitable for recording with a blue laser. In the general formula (1), examples of the substituent represented by R _{1 to} R ₈ are as follows. Hydrogen atom; having 1 to 18 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group and n-heptyl group
A straight-chain or branched alkyl group; a cycloalkyl group having 3 to 18 carbon atoms such as cyclopropyl group, cyclopentyl group, cyclohexyl group and adamantyl group; a straight-chain or branched alkyl group having 2 to 18 carbon atoms such as vinyl group, propenyl group and hexenyl group. A chain or branched alkenyl group; a cycloalkenyl group having 3 to 18 carbon atoms such as a cyclopentenyl group and a cyclohexenyl group; a 2-thienyl group, a 2-pyridyl group, a furyl group, a thiazolyl group, a benzothiazolyl group, a morpholino group and a pyrrolidinyl group Or a saturated or unsaturated heterocyclic group such as a tetrahydrothiophene dioxide group; an aryl group having 6 to 18 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, and a mesityl group; 20 aralkyl groups; acetyl, propionyl, butyryl, isobutyryl, valeryl Having 2 to 2 carbon atoms, such as isovaleryl group
18 straight-chain or branched acyl groups; having 1 to 1 carbon atoms such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group and tert-butoxy group
A linear or branched alkoxy group having 18 to 18 carbon atoms; a linear or branched alkenyloxy group having 3 to 18 carbon atoms such as a propenyloxy group, a butenyloxy group, and a pentenyloxy group; a methylthio group, an ethylthio group, an n-propylthio group, and an n- A linear or branched alkylthio group having 1 to 18 carbon atoms such as a butylthio group, a sec-butylthio group, a tert-butylthio group; a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a nitro group; a cyano group; Formyl group; sulfonic acid group; carboxyl group; acyloxy group represented by —OCOR ₉ ; amino group represented by —NR ₁₀ R ₁₁ ;
In -CONR ₁₆ R _17; carboxylic acid ester group represented by -COOR _15; sulfonamide group represented by -NHSO ₂ R _14; carbamate group represented by -NHCOOR _13; acylamino group represented by OR ₁₂ the sulfamoyl group represented by -SO ₂ NR ₁₈ R _19; carbamoyl group represented;
Sulfonic acid ester groups represented by -SO ₃ R ₂₀ can be mentioned.

The substitution position is not particularly limited.
May have the same substituent or different substituents. Also
R₁~ R₈Of which two adjacent rings form a ring
Represents a quinoline ring or 1,8-naphthyridine which is a basic skeleton
A saturated or unsaturated hydrocarbon ring or rings
Prime ring, R₇And R₈Forms with the nitrogen atom
Nitrogen-containing heterocyclic ring such as
A morpholinyl group containing ₇And R₈, R₇And R₆,
Or R₈And R_FiveAnd a jurolidine ring formed by bonding
No. Even if these rings further have a substituent,
good.

As an example having such a ring, the following structure is exemplified.

[0012]

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Although not described in the above structural formula, the ring formed by bonding two adjacent ones out of R _{1 to} R ₈ in each compound may have a substituent. R _{9 to} R ₂₀ each represent a hydrogen atom, a linear or branched or cyclic alkyl group which may be substituted, a linear or branched or cyclic alkenyl group which may be substituted, an aryl group which may be substituted or Represents an aralkyl group which may be substituted. Also, R ₁
Alkyl groups included in the group represented by to R _20, an alkenyl group, an aryl group, a heterocyclic group may be further substituted. As the substituent in this case, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, etc.
10 alkoxy groups; a methoxymethoxy group, an ethoxymethoxy group, a propoxymethoxy group, an ethoxyethoxy group, a propoxyethoxy group, a methoxybutoxy group or the like alkoxyalkoxy group having 2 to 12 carbon atoms; a methoxymethoxymethoxy group, a methoxymethoxyethoxy group, Methoxyethoxymethoxy group, methoxymethoxyethoxy group,
An alkoxyalkoxyalkoxy group having 3 to 15 carbon atoms such as an ethoxyethoxymethoxy group; an allyloxy group; an aryl group having 6 to 12 carbon atoms such as a phenyl group, a tolyl group, and an xylyl group (even if these are further substituted with a substituent, An aryloxy group having 6 to 12 carbon atoms such as a phenoxy group, a tolyloxy group, a xylyloxy group, and a naphthyloxy group; an alkenyloxy group having 2 to 12 carbon atoms such as an allyloxy group and a vinyloxy group; an acetyl group and a propionyl group Acyl group such as cyano group; nitro group; hydroxyl group; tetrahydrofuryl group; amino group; carbon number 1 such as N, N-dimethylamino group, N, N-diethylamino group
An alkylamino group having 1 to 10 carbon atoms; an alkylsulfonylamino group having 1 to 6 carbon atoms such as a methylsulfonylamino group, an ethylsulfonylamino group, and an n-propylsulfonylamino group; a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; Carbonyl group, ethoxycarbonyl group, n-
An alkoxycarbonyl group having 2 to 7 carbon atoms such as a propoxycarbonyl group, an isopropoxycarbonyl group, and n-butoxycarbonyl; a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an isopropylcarbonyloxy group, and an n-butyl An alkylcarbonyloxy group having 2 to 7 carbon atoms such as a carbonyloxy group; a carbon atom having 2 carbon atoms such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an isopropoxycarbonyloxy group, an n-butoxycarbonyloxy group; To 7 alkoxycarbonyloxy groups and the like. Substituent R of carbostyril compound
_{1 to} R ₆ , substituents R _{1 to} R _{5 of the} 1,8-naphthyridine compound
And preferably a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group, an alkenyl group, an aralkyl group, an alkoxy group, an alkylthio group, an alkenyloxy group, an aryl group, a saturated or unsaturated heterocyclic ring. Group, halogen atom, nitro group, cyano group, formyl group, hydroxy group, carboxyl group, sulfonic acid group, amino group, acylamino group, carbamate group, sulfonamide group, carbamoyl group, carboxylate group, sulfamoyl group, sulfonic acid An ester group, or
Two adjacent groups out of _{1 to} R ₆ combine to form a saturated or unsaturated hydrocarbon ring or heterocyclic ring.

More preferred are a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group, an aralkyl group, an alkoxy group, an alkylthio group, an aryl group, a saturated or unsaturated heterocyclic group, a halogen atom, Nitro group,
Cyano group, hydroxy group, carboxyl group, amino group,
An acylamino group, a carbamate group, a sulfonamide group, a carbamoyl group, a carboxylate group,
Alternatively, two adjacent R _{1 to} R ₆ are bonded to form 5 to 6
This is the case where a membered saturated hydrocarbon ring or a saturated heterocyclic ring is formed.

Particularly preferred are a hydrogen atom and carbon number 1-6.
Alkyl group, aryl group having 6 to 18 carbon atoms, 7 carbon atoms
-18 aralkyl group, C2-C18 linear or branched alkenyl group, C1-C6 alkoxy group, C1-C6 fluoroalkyl group, C1-C6 fluoroalkoxy group, C-carbon number Examples thereof include a 1 to 6 fluoroalkylthio group, a halogen atom, a nitro group, a cyano group, a substituted amino group, an acyl group, and a carboxylate group, and most preferably a hydrogen atom and an alkyl group having 1 to 6 carbon atoms. Preferred as R ₇ and R ₈ are a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group, an alkenyl group, an acyl group, or R ₇ and R ₈ , R
It is a ring formed by bonding ₇ and R ₆ , or R ₈ and R ₅ .

More preferably, a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 18 carbon atoms, a linear or branched alkenyl group having 2 to 18 carbon atoms, an acyl group, or R ₇ and R ₈ , R ₇ and R ₆ , or R
_It is a saturated hydrocarbon ring or a saturated heterocyclic ring formed by bonding ₈ and R ₅ . Among them, a hydrogen atom and carbon number 1 are particularly preferable.
And 6 is a saturated hydrocarbon ring which is condensed between straight-chain or branched alkyl groups and adjacent substituents which may have a substituent. Preferred examples of the compound represented by the general formula [I] include the following.

[0017]

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[0018]

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[0019]

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[0020]

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[0021]

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[0022]

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[0023]

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[0024]

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[0025]

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The metal chelate dyes of the present invention are used, for example, when forming a recording layer from a solution containing the dyes.
Since it has excellent thin film forming properties, it is extremely useful as a dye for use in a recording layer of an optical recording medium. In addition, the metal chelate dye of the present invention is compatible with short-wavelength lasers because the recording layer containing the dye has absorption in a shorter wavelength region (350 nm to 500 nm) of an intensity suitable for recording / reproducing by laser light. It is extremely useful as a dye for use in optical recording media for recording and reproduction.

The optical recording medium of the present invention is basically composed of a substrate and a recording layer containing the above compound. If necessary, an undercoat layer, a metal reflective layer, a protective layer, A layer or the like may be provided. An example of a preferable layer configuration includes a medium having a high reflectance in which a metal reflective layer such as gold, silver, and aluminum and a protective layer are provided on the recording layer.

Hereinafter, the optical recording medium of the present invention will be described using the medium having this structure as an example. The material of the substrate in the optical recording medium of the present invention may be basically any material as long as it is transparent at the wavelength of the recording light and the reproducing light. Examples of such a material include a resin such as an acrylic resin, a methacrylic resin, a polycarbonate resin, a polyolefin resin (especially an amorphous polyolefin), a polyester resin, a polystyrene resin, an epoxy resin, and a glass. Alternatively, a material in which a resin layer made of a radiation-curable resin such as a photo-curable resin is provided on glass can be used.

From the viewpoints of high productivity, cost and moisture absorption resistance, injection molded polycarbonate is preferred. chemical resistance,
An amorphous polyolefin is preferred from the viewpoint of moisture absorption resistance and the like. Further, a glass substrate is preferable from the viewpoint of high-speed response and the like. A resin substrate or a resin layer may be provided in contact with the recording layer, and a guide groove or pit for recording / reproducing light may be provided on the resin substrate or the resin layer. If the guide groove is spiral,
Preferably, the groove pitch is about 0.5 to 1.2 μm. A recording layer containing the compound of the present invention is formed on a substrate or, if necessary, an undercoat layer or the like.

The recording layer may be formed by a vacuum evaporation method,
Sputtering method, doctor blade method, casting method,
Examples of the method generally include a thin film forming method such as a spin coating method and an immersion method. The spin coating method is preferred from the viewpoint of mass productivity and cost. Further, from the viewpoint that a recording layer having a uniform thickness can be obtained, a vacuum deposition method or the like is more preferable than a coating method.

In the case of film formation by the spin coating method, the number of rotation is preferably 500 to 15000 rpm, and after spin coating, a treatment such as heating or exposure to a solvent vapor may be performed in some cases. When forming the recording layer by a coating method such as a doctor blade method, a casting method, a spin coating method, and a dipping method, the coating solvent is not particularly limited as long as it does not attack the substrate. For example, ketone alcohol solvents such as diacetone alcohol and 3-hydroxy-3-methyl-2-butanone; cellosolve solvents such as methyl cellosolve and ethyl cellosolve; chain hydrocarbon solvents such as n-hexane and n-octane ; Cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane,
Cyclic hydrocarbon solvents such as n-butylcyclohexane, tert-butylcyclohexane, and cyclooctane; Perfluoroalkyl alcohol solvents such as tetrafluoropropanol, octafluoropentanol, and hexafluorobutanol; methyl lactate, ethyl lactate, and methyl isobutyrate And the like.

In the case of the vacuum vapor deposition method, for example, the compound of the present invention and, if necessary, the components of the recording layer such as other dyes and various additives are placed in a crucible placed in a vacuum container, and the inside of the vacuum container is charged. After evacuating to about 10 ⁻² to 10 ⁻⁵ Pa with a suitable vacuum pump, the crucible is heated to evaporate the recording layer components,
The recording layer is formed by vapor deposition on a substrate placed facing the crucible. Further, the recording layer is formed of a transition metal chelate compound (eg, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α-diketone, etc.) as a singlet oxygen quencher in order to improve the stability and light resistance of the recording layer. ) Etc.,
In order to improve the recording sensitivity, a recording sensitivity improver such as a metal compound may be contained. Here, the metal compound refers to a compound in which a metal such as a transition metal is contained in the compound in the form of an atom, an ion, a cluster, or the like. Organometallic compounds such as dihydroxyazobenzene-based complexes, dioxime-based complexes, nitrosoaminophenol-based complexes, pyridyltriazine-based complexes, acetylacetonate-based complexes, metallocene-based complexes, and porphyrin-based complexes are exemplified. The metal atom is not particularly limited, but is preferably a transition metal. Further, if necessary, other types of dyes may be used in combination. Other dyes may be used as long as they have appropriate absorption mainly in the laser wavelength range for recording.
There is no particular limitation. In addition, a near-infrared laser with a wavelength selected from 770 to 830 nm, such as a CD-R, or a 620 to 69, such as a DVD-R,
An optical recording medium that can be used for recording with laser light in a plurality of wavelength ranges can be used in combination with a dye suitable for recording with a red laser selected from 0 nm. Other dyes include metal-containing azo dyes, phthalocyanine dyes, naphthalocyanine dyes, cyanine dyes, azo dyes,
Squarylium dyes, metal-containing indoaniline dyes,
Triarylmethane dyes, merocyanine dyes, azurenium dyes, naphthoquinone dyes, anthraquinone dyes, indophenol dyes, xanthene dyes,
Oxazine-based dyes and pyrylium-based dyes are exemplified.
Further, if necessary, a binder, a leveling agent, an antifoaming agent and the like can be used in combination. Preferred binders include polyvinyl alcohol, polyvinyl pyrrolidone, nitrocellulose, cellulose acetate, ketone resin, acrylic resin, polystyrene resin, urethane resin, polyvinyl butyral, polycarbonate, polyolefin and the like.

The film thickness of the recording layer is not particularly limited because the film thickness suitable for the recording method and the like differs, but is usually not limited.
50-300 nm. A reflective layer may be formed on the recording layer, and its thickness is preferably 50 to 300 nm. As a material of the reflection layer, one having a sufficiently high reflectance at the wavelength of the reproduction light, for example, Au, Al, Ag, Cu, Ti, Cr, Ni, P
The metals t, Ta, Cr and Pd can be used alone or as an alloy. Among them, Au, Al, and Ag have high reflectivity and are suitable as the material of the reflective layer. In addition to these as main components, the following may be included. For example, M
g, Se, Hf, V, Nb, Ru, W, Mn, Re, Fe, Co, Rh, I
r, Cu, Zn, Cd, Ga, In, Si, Ge, Te, Pb, Po, Sn, Bi
And metal and semimetals. Especially
Those containing Ag as a main component are particularly preferable in that they are inexpensive, easily provide high reflectivity, and when a print-receiving layer described later is provided, a white and beautiful ground color can be obtained. Here, the main component means one having a content of 50% or more. It is also possible to form a multilayer film by alternately stacking low-refractive-index thin films and high-refractive-index thin films with a material other than a metal and use it as a reflective layer.

As a method of forming the reflection layer, for example,
Examples include a sputtering method, an ion plating method, a chemical vapor deposition method, and a vacuum vapor deposition method. In addition, a known inorganic or organic intermediate layer or adhesive layer may be provided on the substrate or under the reflective layer to improve the reflectance, the recording characteristics, and the adhesion. The material of the protective layer formed on the reflective layer is not particularly limited as long as it protects the reflective layer from external force. As organic material, thermoplastic resin,
Thermosetting resin, electron beam curable resin, UV curable resin, and the like can be given. In addition, as the inorganic substance, SiO
2, SiN4, MgF2, SnO2 and the like. A thermoplastic resin, a thermosetting resin, or the like can be formed by dissolving in an appropriate solvent, applying a coating solution, and drying.
The UV curable resin can be formed by preparing a coating solution as it is or by dissolving it in an appropriate solvent, applying the coating solution, and irradiating with UV light to cure the resin. As the UV-curable resin, for example, acrylate resins such as urethane acrylate, epoxy acrylate, and polyester acrylate can be used.
These materials may be used alone or as a mixture, or may be used as a multilayer film instead of a single layer. As a method for forming the protective layer, a coating method such as a spin coating method or a casting method, a sputtering method, a chemical vapor deposition method, or the like is used as in the case of the recording layer. Among them, the spin coating method is preferable.

The thickness of the protective layer is generally in the range of 0.1 to 100 μm, but is preferably 3 to 30 μm in the present invention. Further, a substrate may be further bonded to the reflection layer surface,
Further, two optical recording media may be bonded to each other such that the surfaces of the reflective layers face each other as inner surfaces. An ultraviolet curable resin layer, an inorganic thin film, or the like may be formed on the mirror surface of the substrate to protect the surface or prevent adhesion of dust and the like.

It should be noted that, on the surface other than the recording / reproducing light incident surface,
A print receiving layer that can be filled in (printed) with various printers such as ink jet and thermal transfer, or various writing tools may be provided. The laser beam used for the optical recording medium of the present invention is preferably shorter in wavelength for high-density recording, but a laser beam of 350 to 530 nm is particularly preferable. Representative examples of such laser light include laser light having center wavelengths of 410 nm and 515 nm.

An example of laser light having a wavelength in the range of 350 to 530 nm can be obtained by using a high-power semiconductor laser of blue of 410 nm or blue-green of 515 nm. A semiconductor laser capable of continuous oscillation of 740 to 960 nm, or (b) a solid-state laser excited by the semiconductor laser and having a fundamental oscillation wavelength of 740 to 960 nm.
It can also be obtained by wavelength conversion by (SHG). The SHG may be any element as long as it is a piezo element lacking inversion symmetry, but includes KDP, ADP,
BNN, KN, LBO, compound semiconductor and the like are preferable.
Specific examples of the second harmonic include a semiconductor laser having a fundamental oscillation wavelength of 860 nm, a harmonic of 430 nm, and a solid-state laser excited by a semiconductor laser, a Cr-doped Li.
430nm of harmonics from SrAlF6 crystal (basic oscillation wavelength 860nm)
And the like. The recording on the optical recording medium of the present invention obtained as described above is performed by irradiating the recording layer provided on both sides or one side of the substrate with a laser beam focused to about 0.4 to 0.6 μm. Decomposition, heat generation, due to the absorption of laser light energy
Thermal deformation of the recording layer such as dissolution occurs, and the optical characteristics change.

Reproduction of recorded information is performed by reading the difference in reflectance between a portion where optical characteristics have changed and a portion where optical characteristics have not changed using a laser beam.

[0039]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples unless it exceeds the gist. [Synthesis Method of Compound] As for the synthesis method of 7-amino-substituted carbostyril, a plurality of synthesis methods have been reported so far.
As a general production method, a cyclization reaction between an m-phenylenediamine derivative and a β-ketoester derivative as shown in the following formula 10 can be mentioned (ref. JOC56, 3 (1991) 980, J. Me.
d. Chem. 31, 7 (1988) 1347). These reactions are 1,8
-It can also be applied to the synthesis of naphthyridine.

[0040]

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Also, a method for synthesizing a 7-acylamino compound
Is, for example, 7-aminocarbo
By stirring styryl in acetic anhydride in the presence of sulfuric acid
It is reported that it can be synthesized (J. Chem. Eng.data.1
3,3 (1968) 440). Example 1 4-methyl-7- represented by the aforementioned exemplary compound (1)
Amino-2 (1H) -quinolone (acros; chloropho
Maximum absorption wavelength in lum (λmax) = 348 nm, molar absorption
Number 1.7 × 10^Four) In octafluoropentanol,
It was adjusted to 1.0 wt%. The solution obtained by filtration is
120mm, 1.2mm thick injection molded polycarbonate resin substrate
Drop it on top, apply by spin coating method, and after application,
Dry at 00 ° C. for 30 minutes. Λmax of this coating film is 353 nm
Met. Example 2 4-methyl-7-dimethyl represented by the exemplified compound (2)
Amino-2 (1H) -quinolone (acros; chloropho
Λmax = 363 nm, molar extinction coefficient 2.1 × 10 ^Four)
Dissolve in Kutafluoropentanol, adjust to 1.0 wt%
Was. The solution obtained by filtering this is 120 mm in diameter and 1.2 mm in thickness.
mm on an injection-molded polycarbonate resin substrate.
Apply by pin coating method, and after application, at 100 ° C for 30 minutes
While drying. Λmax of this coating film was 380 nm. Example 3

[0042]

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4.93 g (0.03 mol) of N, N-diethyl-m-phenylenediamine represented by the above structural formula
l) and 5.77 g of ethyl benzoylacetate represented by
(0.03 mol) was heated at 180 ° C. for 9 h by an oil bath while stirring. Thereafter, 20 ml of methanol was added to the solid precipitated by heating, the mixture was refluxed for 1 hour, and the product was filtered. The filtrate is methanol 50
suspended for 1 h at room temperature and filtered.
By drying the filtrate, 1.31 g of the product represented by the exemplary compound (3) was obtained. Λmax in chloroform of the product is 373.5 nm, molar extinction coefficient 2.1 × 10 ⁴
Met.

This compound was dissolved in octafluoropentanol and adjusted to 1.0 wt%. A solution obtained by filtering this is dropped on an injection molded polycarbonate resin substrate having a diameter of 120 mm and a thickness of 1.2 mm, and applied by a spin coating method,
After the application, it was dried at 100 ° C. for 30 minutes. Λ of this coating film
max was 382 nm. Examples 4 to 12 Hereinafter, exemplified compounds (4) to (1) according to the above-mentioned synthesis method.
The compound of 1) was synthesized, and the film spectrum was measured.

The exemplified compound (12) is described in Eur.
d. Chem. 33 (1998) 383, a synthesis was carried out, and DMF was used as a coating solvent and ZEONEX base was used as a coating base. The maximum absorption wavelength of these compounds in solution, the molar extinction coefficient, and the maximum absorption wavelength of the coating film were determined in Examples 1 to 3.
Table 1 shows the results together with the results.

[0046]

[Table 1]

For example, a silver film is formed on this coating film by a sputtering method or the like to form a reflective layer, and an ultraviolet curable resin is applied by spin coating or the like and cured by UV irradiation to form a protective layer. Formed into an optical recording medium. It is clear from the value of λmax of the coating film that this optical recording medium can be recorded / reproduced by a semiconductor laser having a center wavelength of 410 nm, for example.

[0048]

The solution containing the compound of the present invention can form a coating film having an absorption suitable for recording / reproducing by short-wavelength laser light and has excellent film-forming properties.
A recording medium having a recording layer using the compound of the present invention is useful as an optical recording medium for recording and reproduction corresponding to a short wavelength laser.

[Brief description of the drawings]

FIG. 1 is an absorption spectrum of a compound synthesized in Example 3 in a chloroform solution.

FIG. 2 is an absorption spectrum of a coating film of a compound synthesized in Example 3.

FIG. 3 is an absorption spectrum of a compound synthesized in Example 8 in a DMF solution.

FIG. 4 is an absorption spectrum of a compound synthesized in Example 8 in a coating film.

Claims (5)

[Claims] 1. A method of recording information on a substrate by using a laser.
And / or optical recording medium provided with a reproducible recording layer
Wherein the recording layer has a power represented by the following general formula [I]:
Rubostyryl compound or 1,8-naphthyridine compound
An optical recording medium comprising: Embedded image(Wherein X is a nitrogen atom or C—R₆Represents R₁,
R_Two, R_Three, R_Four, R_Five, R₆, R₇And R₈Respectively
Independently represents a hydrogen atom or any substituent. Also R ₁
~ R₈Two of the two are linked to form a ring
Is also good. ) 2. In the general formula [I], R ₁ , R ₂ , R ₃ ,
R ₄ , R ₅ and R ₆ are each independently a hydrogen atom,
Optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkoxy, alkylthio, aralkyl, alkenyloxy, aryl, saturated or unsaturated heterocyclic groups, halogen atoms , Selected from nitro, cyano, formyl, hydroxy, carboxyl, sulfonic, amino, acylamino, carbamate, sulfonamide, carbamoyl, carboxylate, sulfamoyl and sulfonate groups 2. The optical recording medium according to claim 1, wherein adjacent two of R _{1 to} R ₈ may be bonded to form a ring. 3. The method of claim ₁ , wherein R ₁ , R ₂ , R ₃ ,
R ₄ , R ₅ and R ₆ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group, an aralkyl group, an alkoxy group, an alkylthio group, an aryl group,
A group selected from a saturated or unsaturated heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an amino group, an acylamino group, a carbamate group, a sulfonamide group, a carbamoyl group, and a carboxylate group. The optical recording medium according to claim 2, wherein two or more of R _{1 to} R ₆ are adjacent to each other to form a ring. 4. In the general formula [I], R ₇ and R ₈ are
Each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, or an acyl group which may have a substituent, provided that R ₇ and R ₈ , R ₇ and R ₆ , and R ₈ and R ₅ Characterized in that one or more of may combine to form a ring,
The optical recording medium according to claim 1. 5. The laser wavelength for recording or reproducing information is 35.
The optical recording medium according to claim 1, wherein the optical recording medium has a thickness of 0 nm to 530 nm.