JPH10273484A - Metal chelate azomethine compound and optical recording medium using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful for a coloring matter suitable in a recording layer of an optical recording medium, comprising an azomethine compound. SOLUTION: This metal chelate azomethine compound comprises an azomethine compound of the formula (A is a heterocyclic ring-forming residue; B is an aromatic or a heterocyclic ring-forming residue; X is an active hydrogen- containing group) forming a chelate with a metal. The compound is obtained by reacting an azomethine compound of the formula with a metal salt in a solvent such as THF. In the reaction, BF4 <-> , PF6 <-> or CH3 COO<-> is preferable as the anion of the metal salt used. The compound of the formula is obtained by condensing a formyl compound with an amino compound through dehydration. The subject compound has high solubility in an organic solvent, is capable of being coated by application and has improved sensitivity and excellent light resistance and shelf stability. An optical recording medium using the compound is suitable as CD media DVD media equipped with a metal reflecting layer and a protective layer on a recording layer.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel metal chelate azomethine compound of an azomethine compound and a metal, and an optical recording medium using the same.

[0002]

2. Description of the Related Art Optical recording using a laser can record, store and reproduce information at high density.
Its development is particularly active. As an example of optical recording,
An optical disk can be mentioned. Generally, an optical disc performs high-density information recording by irradiating a thin recording layer provided on a circular substrate with a laser beam focused to about 1 μm. The recording is performed by absorbing the irradiated laser beam energy, thereby generating thermal deformation such as decomposition, evaporation, and dissolution in the recording layer at that location. Reproduction of recorded information is performed by reading a difference in reflectance between a portion where deformation has occurred and a portion where no deformation has occurred due to laser light. Therefore, the recording layer needs to efficiently absorb the energy of laser light, and a laser absorbing dye is used.

Various types of optical recording media are known as such optical recording media. For example, JP-A-55-97
No. 033 discloses that a single layer of a phthalocyanine dye is provided on a substrate. However, phthalocyanine dyes have problems such as low sensitivity, high decomposition point, and difficulty in vapor deposition, and further, they have a problem that they cannot be used for coating by application due to extremely low solubility in organic solvents. doing.

Further, Japanese Patent Application Laid-Open Nos. 58-112790 and 5
Nos. 8-114989, 59-85791, 60-
Each of JP-A-83236 and the like discloses a recording medium provided with a recording layer using a cyanine dye. However, this dye has a high solubility, and has an advantage that it can be coated by application, but has a problem of poor light resistance. For this reason, JP-A-59-55795 discloses that
It has been studied to improve the light fastness by adding a quencher to this cyanine dye, but the level is still insufficient.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a recording dye which solves the above problems, and an optical recording medium using the same.

[0006]

The dye according to the present invention is a metal chelate azomethine compound in which an azomethine compound represented by the following general formula [I] forms a chelate with a metal.

[0007]

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Wherein A represents a residue which, together with the carbon and nitrogen atoms to which it is attached, forms a heterocycle, and B, together with the two carbon atoms to which it is attached, Represents an aromatic ring or a heterocyclic ring, and X represents a group having active hydrogen.)

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail. In the general formula [I], a residue A forms a heterocyclic ring together with a carbon atom and a nitrogen atom to which it is bonded. The following are preferred as the heterocyclic ring formed by the residue A.

[0010]

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[0011]

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[0012]

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(Wherein R ^{1 to} R ⁸ are each independently a hydrogen atom; a methyl group, an ethyl group, an n-propyl group,
Isopropyl group, n-butyl group, tert-butyl group,
an alkyl group having 1 to 7 carbon atoms such as sec-butyl group, n-pentyl group, n-hexyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, tert-butoxy group, sec-butoxy group, n
-An alkoxy group having 1 to 8 carbon atoms such as a pentyloxy group and an n-hexyloxy group; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group; alkylsulfonyl and alkoxysulfonyl groups having 1 to 6 carbon atoms such as n-pentyl and n-hexyl; phenylsulfonyl; acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl Group, hexanoyl group, heptanoyl group, etc.
An alkylcarbonyl group; a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a formyl group; -CR ⁹ CR ¹⁰
(CN) (where R ⁹ is a hydrogen atom or the aforementioned R ^{1 to} R ⁸
Represents an alkyl group having 1 to 6 carbon atoms as defined above, and R ¹⁰ represents a cyano group or a methoxycarbonyl group,
An ethoxycarbonyl group, an n-propoxycarbonyl group,
Isopropoxycarbonyl group, n-butoxycarbonyl group, tert-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, n
-Represents an alkoxycarbonyl group having 2 to 7 carbon atoms such as a hexyloxycarbonyl group. ); Nitro group;

[0014]

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(Where R ^{11 to} R ¹³ each independently represent a hydrogen atom or a nitro group, Z is a single bond, —SC
H ₂ -, - SO ₂ - or -SO ₂ CH ₂ - represents a. );
Fluoroalkyl group and a fluoroalkoxy group having 1 to 3 carbon atoms, cyano groups, the alkoxycarbonyl group was those with synonymous 2-7 carbon atoms defined in R ^10; methoxycarbonylmethyl, methoxycarbonylethyl group,
C3-7 carbon atoms such as an ethoxycarbonylmethyl group, an ethoxycarbonylethyl group, an n-propoxycarbonylmethyl group, an n-propoxycarbonylethyl group, an n-propoxycarbonylpropyl group, an isopropoxycarbonylmethyl group, and an isopropoxycarbonylethyl group; Alkoxycarbonylalkyl group; or methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n
-Alkylthio group having 1 to 7 carbon atoms such as -butylthio group, tert-butylthio group, sec-butylthio group, n-pentylthio group, n-hexylthio group; fluoroalkylthio group having 1 to 3 carbon atoms; and phenylazo group. Residue A
Is more preferably one of the following.

[0016]

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In the formula, P ¹ , P ² , P ³ and P ⁴ each independently represent an isopropyl group, a tert-butyl group,
branched alkyl groups having 3 to 7 carbon atoms, such as sec-butyl group and 2,4-dimethyl-3-pentyl group; and isopropoxy group, tert-butoxy group, 2,4-dimethyl-3-pentyloxy group, etc. A branched alkoxy group having 3 to 8 carbon atoms;
Isopropylthio group, tert-butylthio group, sec
A branched alkylthio group having 3 to 7 carbon atoms such as -butylthio group, 2,4-dimethyl-3-pentylthio group; a fluorine atom; a trifluoromethyl group, a pentafluoroethyl group,
A fluorine-substituted alkyl group having 1 to 3 carbon atoms such as a tetrafluoroethyl group; a carbon atom having 1 to 3 carbon atoms such as a trifluoromethoxy group, a pentafluoroethoxy group, and a tetrafluoroethoxy group;
3 fluorine-substituted alkoxy group; a fluorine-substituted alkylthio group having 1 to 3 carbon atoms, such as a trifluoromethylthio group, a pentafluoroethylthio group, a tetrafluoroethylthio group, and the like.

In the azomethine compound represented by the general formula [I], examples of the aromatic ring or hetero ring formed by B include a benzene ring, a naphthalene ring, a pyridine ring, a pyridone ring, a tetrahydroquinoline ring and a pyrazole ring. These aromatic rings or heterocyclic rings may further have a substituent other than X, and examples of the substituent include an alkyl group, an alkoxy group, an aryloxy group, an aralkyl group, an aryl group, a halogen atom, a cyano group, and a nitro group. Group, ester group,
A carbamoyl group, an acyl group, an acylamino group, a sulfamoyl group, a sulfonamide group, an amino group, a hydroxyl group, a phenylazo group, a pyridinoazo group, a vinyl group, and the like.These substituents may themselves further have a substituent. Good. Among these substituents on the aromatic ring or the heterocyclic ring, preferred are an alkyl group having 1 to 25 carbon atoms which may have a substituent and 1 to 1 carbon atom which may have a substituent. 25 alkoxy groups, halogen atoms, cyano groups, nitro groups, and optionally substituted carbon atoms having 1 to 2 carbon atoms
5, an alkylsulfamoyl group having 5 carbon atoms, a phenylsulfamoyl group having 6 to 30 carbon atoms which may have a substituent, a phenylazo group which may have a substituent, and a substituent Pyridinoazo group, ester group having 2 to 26 carbon atoms, carbamoyl group having 2 to 26 carbon atoms, 2 to 26 carbon atoms
An acyl group having 1 to 25 carbon atoms, a sulfonamide group having 1 to 25 carbon atoms, -NR ¹⁷ R ¹⁸ (R ¹⁷ and R ¹⁸ are each independently a hydrogen atom; and may be substituted. An alkyl group; an aryl group which may be substituted,
Especially a phenyl group; an alkenyl group which may be substituted,
Represents an optionally substituted cycloalkyl group, or may combine R ¹⁷ and R ¹⁸ to form a 5- or 6-membered ring), a hydroxyl group, —CR ¹⁹ ＣC (C
N) R ²⁰ (R ¹⁹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ²⁰ represents a cyano group or an alkoxycarbonyl group having 2 to 7 carbon atoms.), And the like.

In the azomethine compound represented by the general formula [I], X is not particularly limited as long as it is a group having an active hydrogen, but preferred are -OH, -C
_{OOH, -SO 3 H, -B (} OH) 2, -HNSO 2 R
^16, -NHCOR ^16, (representing R ¹⁶ is a hydrogen atom, an alkyl group or an optionally substituted phenyl group that may have a good 25 carbon atoms which may have a substituent.) -NHCOOR ^16, etc. And particularly preferred is -O
_{H, -COOH, -SO 3 H,} -HNSO 2 R 16 (R 16
Is the same as defined above. ). Note that X is -CO
OH, -OH, when a group which can dissociate into an anion as such -SO ₃ H, the time of formation of the azo metal chelate compound may be used in the form of this state, a salt of a cation It may be used in the form. Such cations include N
an inorganic cation such as a ⁺ , Li ⁺ , K ^+, or

[0020]

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And organic cations such as One of the preferred azomethine compounds represented by the general formula [I] is a compound represented by the following general formula [II].

[0022]

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(Wherein, R ¹⁴ and R ¹⁵ each independently represent a hydrogen atom or a C 1-2 carbon atom which may have a substituent)
5 alkyl groups, aryl groups which may have a substituent, particularly phenyl groups, alkenyl groups having 2 to 25 carbon atoms which may have a substituent or carbon atoms which may have a substituent It represents 3 to 25 cycloalkyl groups, or R ¹⁴ and R ¹⁵ are combined to form a 5- or 6-membered ring. A and X have the same meaning as defined above, and ring D may further have a substituent. )

In the general formula [II], R ¹⁴ and R ¹⁵
As a substituent capable of bonding to an alkyl group, an aryl group, an alkenyl group or a cycloalkyl group represented by, for example, an alkoxy group, an alkoxyalkoxy group, an alkoxyalkoxyalkoxy group, an allyloxy group, an aryl group, an aryloxy group, a cyano group, Examples include a nitro group, a hydroxy group, a tetrahydrofuryl group, an alkylsulfonylamino group, a halogen atom, and the like. Further, examples of the substituent of the aryl group include an alkyl group and a vinyl group. Other substituents that can be bonded to ring D include an alkyl group, an alkoxy group, a halogen atom and the like. Some of the azomethine compounds that form chelates with metals according to the present invention are illustrated in Table 1 below.

[0025]

[Table 1]

[0026]

[Table 2]

[0027]

[Table 3]

[0028]

[Table 4]

[0029]

[Table 5]

[0030]

[Table 6]

[0031]

[Table 7]

[0032]

[Table 8]

[0033]

[Table 9]

[0034]

[Table 10]

[0035]

[Table 11]

In the present invention, the metal that forms a chelate with the azomethine compound is not particularly limited as long as it is generally a metal capable of forming a complex with the azo compound, but Ni, Co, Fe, Ru, Rh, Pd, Os,
Transition elements such as Ir and Pt are preferred, and particularly Ni or Co
Is preferred. Next, the method for producing the metal chelate azomethine compound of the present invention will be described. The azomethine compound of the general formula (I) can be produced by dehydration condensation of a formyl compound and an amino compound according to the following formula.

[0037]

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Next, the azomethine compound and the metal salt are mixed with water, dioxane, tetrahydrofuran, acetone,
When the reaction is carried out in an organic solvent such as ethanol, the metal chelate compound of the present invention is obtained. Examples of the anion of the metal salt used for producing the metal chelate compound include SCN ⁻ , SbF
_{^{6 -, Cl -, Br -}} , F -, ClO 4 -, BF 4 -,
_{^{PF 6 -, CH 3 COO -}} , TiF 6 2-, SiF 6 2-,
_{^{Zr 6 2-, Ph-SO 3}} -, CH 3 -Ph-SO 3 -,
A monovalent or divalent anion such as B ^- Ph ₄ (where Ph represents a benzene ring) is preferable, and particularly BF ₄ ^- and P
F ₆ ⁻ and CH ₃ COO ⁻ are preferably used.

Next, the optical recording medium of the present invention will be described. The optical recording medium of the present invention is basically composed of a substrate and a recording layer containing the metal chelate compound of the azomethine compound. If necessary, a subbing layer may be provided on the substrate. Can be. In addition, as a preferable layer configuration, a recording medium is provided with a metal reflection layer such as metal or aluminum and a protective layer made of a resin to provide a medium having high reflectivity, which can be a write-once CD or DVD medium.

The substrate may be either transparent or opaque to the laser light used. As a material of the substrate, a material generally known as a support of the recording material such as glass, plastic, paper, plate-like or foil-like metal is used, but plastic can be suitably used from various points. As plastic, acrylic resin,
Methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, epoxy resin, polysulfone resin, etc.
Injection-molded polycarbonate resin substrates are particularly preferably used in terms of cost and moisture absorption resistance.

The recording layer containing a metal chelate compound of an azomethine compound and a metal in the optical recording medium of the present invention preferably has a thickness of 100 to 5 μm, more preferably 300 to 1200 °. As a film forming method, a film can be formed by a generally used thin film forming method such as a vacuum evaporation method, a sputtering method, and a coating method. However, a coating method is preferable in terms of mass productivity, cost, and the like. As a coating method, any of a doctor blade method, a casting method, a spinner method, and a dipping method can be used, but the spinner method is particularly preferable.

In the case of the coating method, a binder can be used if desired. As the binder, known binders such as polyvinyl alcohol, polyvinyl pyrrolidone, ketone resin, nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate are used. In the case of film formation by the spinner method, the number of rotations is 500 to 5
After spin coating, if necessary, a treatment such as heating or exposure to a solvent vapor can be performed.

In order to improve the stability and light resistance of the recording layer, the recording layer is provided with a transition metal chelate compound (eg, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, distithio-) as a singlet oxygen quencher. α-diketone, etc.), and a dye of the same type or a triarylmethane dye, an azo dye, a cyanine dye, a squalilium dye, a metal chelate compound of a monoazo compound, nickel
Other dyes such as indoaniline dyes can also be used in combination.

When a recording layer is formed on a substrate by a coating method, in particular, a spinner method, examples of a coating solvent include tetrafluoropropanol, octafluoropentanol, tetrachloroethane, bromoform, dibromoethane, diacetone alcohol, ethyl cellosolve, and the like. Xylene, 3-
Boiling point of 120 to 1 for hydroxy-3-methyl-2-butanone, chlorobenzene, cyclohexanone, methyl lactate, etc.
Those at 60 ° C. are preferably used.

Among them, diacetone alcohol and 3-hydroxy-3-ether are preferably used as a solvent which can be suitably used without invading this substrate for an injection molded polycarbonate resin substrate excellent in high productivity, cost and moisture absorption resistance. Ketone alcohol solvents such as methyl-2-butanone; cellosolve solvents such as methyl cellosolve and ethyl cellosolve;
It is preferable to use perfluoroalkyl alcohol solvents such as tetrafluoropropanol and octafluoropentanol; hydroxyester solvents such as methyl lactate and methyl isobutyrate; and hydrocarbon solvents such as ethylcyclohexane and butylcyclohexane. The recording layer of the optical recording medium of the present invention may be provided on both sides of the substrate,
It may be provided only on one side.

The recording on the optical recording medium obtained as described above is performed by recording 1 μm on the recording layer provided on both sides or one side of the substrate.
The irradiation is performed by irradiating a laser beam focused to about m, preferably a semiconductor laser beam. The portion irradiated with the laser light undergoes thermal deformation of the recording layer such as decomposition, evaporation, and melting due to absorption of laser energy. Therefore, the recorded information can be reproduced by reading the difference in reflectance between the portion where thermal deformation has occurred and the portion where thermal deformation has not occurred due to the laser beam. Examples of the laser beam used for recording and reproducing on the optical recording medium of the present invention include N ₂ , He—Cd, Ar, He—Ne, ruby, semiconductor, and dye laser. Semiconductor lasers are preferably used in terms of ease of use and compactness.

[0047]

EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to the examples unless it exceeds the gist. Example 1 (a) Compound Production Example 3-Acetylamino-N, N-diethylaniline 600
of a 50% aqueous acetic acid solution in 7.5 ml.
The mixture was stirred with ice cooling to 0 ° C. or lower, and a solution prepared by dissolving 300 mg of sodium nitrite in 1.5 ml of water was gradually added dropwise to react. After completion of the reaction, the mixture was neutralized with an aqueous solution of sodium carbonate and extracted with chloroform. After the extract was washed with water, the solvent was distilled off. After the residue was separated by column chromatography, the solvent was distilled off to obtain 565 mg of green crystals of a nitroso compound. ¹ H-NMR (CDCl ₃ ): δ ppm: 12.66
(S, 1H), 8.38 (d, 1H), 8.03 (d,
1H), 6.63 (dd, 1H), 3.56 (q, 4
H), 2.22 (s, 3H), 1.32 (t, 6H)

Next, 500 mg of this nitroso compound was dissolved in 6 ml of dry methanol, and 200 mg of sodium borohydride and 80 mg of palladium carbon were added thereto.
mg was added and stirred under a nitrogen atmosphere. After 2 hours, suction filtration was performed to remove palladium carbon. 457 mg of 2-pyridinecarbaldehyde was added to the filtrate, and the pH was adjusted with dilute hydrochloric acid.
Was adjusted to neutral and stirred for 1 hour. The reaction solution was extracted with chloroform, the extract was washed with water, and the solvent was distilled off. The residue was separated by column chromatography and then crystallized to obtain 356 mg of yellow crystals of an azomethine compound having the structure A-1 in Table 1 (54% yield).

MASS (EI): 310 (M ⁺ ) UV-vis spectrum (ethanol): λmax43
A solution of 294 mg of nickel perchlorate hexahydrate in 2 ml of water was added dropwise to 100 mg of this azomethine compound in 3 ml of 3 nm methanol while stirring. 3
After stirring for 0 minutes, the mixture was filtered to obtain 82 mg of a precipitate of a nickel chelate compound. FIG. 1 shows the absorption spectrum of this compound in an ethanol solution. UV-vis spectrum (ethanol): λmax48
8 nm

(B) Production Example of Optical Recording Medium 0.15 g of a metal chelate compound of an azomethine compound and nickel obtained by the same method as in the above Production Example (a) was dissolved in 7.5 g of octafluoropentanol. .22 μm
Was filtered. 5 ml of this solution has a depth of 700
Å, dropped onto a 5 inch diameter injection molded polycarbonate resin substrate having a 0.7 μm wide groove (groove) and applied by a spinner method at a rotation speed of 500 rpm. After the application, it was dried at 100 ° C. for 1 hour. Next, a gold film having a film thickness of 800 ° was formed on this coating film by a sputtering method to form a reflection layer. Further, after spin-coating an ultraviolet-curable resin CD-318 (a product of Dainippon Ink Co., Ltd.) on the reflective layer, it is cured by irradiating ultraviolet rays to form a protective layer having a thickness of 5 μm. Manufactured.

(C) Optical Recording Example The optical recording medium obtained in the above-mentioned Production Example (b) was prepared as follows.
When the EFM signal was recorded and the initial characteristics were evaluated using a 5 nm semiconductor laser, the bit length jitter was good.
A recording portion having a good rim shape was obtained. After a high-temperature and high-humidity test for 500 hours at a temperature of 80 ° C. and a humidity of 90%, a change in the block error rate was measured. As a result, only a slight increase in the error was observed.

Examples 2 to 4 An optical recording medium was produced in the same manner as in Example 1, except that the solution of the metal chelate azomethine compound in Table 2 was used. When this recording medium was tested in the same manner as in Example 1, both the recording of the EFM signal and the evaluation of the initial characteristics were good, and a recording portion having a good rim shape was obtained. When a high-temperature and high-humidity test was performed in the same manner as in Example 1, only a slight increase in error was observed.

[0053]

[Table 12]

Example 5 A 0.6 mm thick polycarbonate substrate having a U-shaped guide groove having a depth of 150 nm, a width (half width) of 0.25 μm, and a pitch of 0.80 μm (measured by AFM) was prepared as shown in Table 1.
A-5, a solution of a metal chelate azomethine compound of the azomethine compound of A-5 and a nickel salt dissolved in octafluoropropanol to a concentration of 2.5% by weight was applied by a spinner method, and dried by a dryer at 100 ° C. for 30 minutes. . Next, gold was formed on the dye layer by a DC magnetron sputtering method so as to have an average thickness of 100 nm to form a reflective layer. Further, on this reflective layer, a UV-curable resin SD-318 was dried by a spinner method to a dry thickness of 4 μm.
m, and cured by irradiating with an ultraviolet ray with an ultraviolet ray irradiator to form a protective layer. The two disks manufactured in this manner were bonded by a hot melt method to obtain an optical recording medium.

The recording medium was subjected to recording of the EFM signal and evaluation of the initial characteristics using a semiconductor laser evaluator (numerical aperture NA = 0.6) having a wavelength of 640 nm. A rim-shaped recording section was obtained. 500 under conditions of temperature 80 ° C and humidity 90%
After a long time high temperature and high humidity test, the change in block error rate was measured, and only a slight increase in error was observed.

[0056]

The metal chelate compound of the azomethine compound of the present invention has high solubility in an organic solvent, can be coated by coating, and has excellent sensitivity, light resistance and storage stability. An optical recording medium using this metal chelate compound has high sensitivity and excellent recording / reproducing characteristics, and particularly has excellent light resistance and storage stability. It is suitable for CD media and DVD media provided with a protective layer.

[Brief description of the drawings]

FIG. 1 is an absorption spectrum of an azomethine compound which forms a chelate with nickel obtained in Example 1.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 235/14 C07D 263/56 263/56 277/28 277/28 277/60 277/60 277/64 277/64 277/84 277/84 285/08 285/08 401/12 213 285/12 235 285/13 409/14 213 285/125 413/12 213 401/12 213 417/12 213 235 231 409/14 213 471/04 101 413 / 12 213 513/04 301 417/12 213 343 231 C09B 55/00 D 471/04 101 G11B 7/24 516 513/04 301 B41M 5/26 Y 343 C07D 285/12 C09B 55/00 A G11B 7/24 516 CD

Claims (9)

[Claims] 1. A metal chelated azomethine compound in which the azomethine compound represented by the following general formula [I] forms a chelate with a metal. Embedded image Wherein A represents a residue which forms a heterocyclic ring together with the carbon and nitrogen atoms to which it is attached, and B represents an aromatic group which is taken together with the two carbon atoms to which it is attached. Represents a residue forming a ring or a heterocyclic ring, and X represents a group having active hydrogen.) 2. The heterocyclic ring formed by the residue A in the general formula [I] together with a carbon atom and a nitrogen atom is selected from the group consisting of a heterocyclic ring represented by the following formula: The metal chelate azomethine compound according to claim 1, wherein Embedded image Embedded image Embedded image 中 In each formula, R ^{1 to} R ⁸ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, 2 to 7 alkylcarbonyl groups, halogen atoms, formyl groups, —CR ⁹ ＣＲCR ¹⁰ (CN) (where R ⁹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ¹⁰ represents a cyano group or Represents an alkoxycarbonyl group having 2 to 7 carbon atoms), a nitro group, (Where R ^{11 to} R ¹³ each independently represent a hydrogen atom or a nitro group, Z is a single bond, —SCH ₂ —, —S
Represents O ₂ — or —SO ₂ CH ₂ —. ), A trifluoromethyl group, a trifluoromethoxy group, a cyano group, an alkoxycarbonyl group having 2 to 7 carbon atoms, an alkoxycarbonylalkyl group having 3 to 7 carbon atoms, or an alkylthio group having 1 to 6 carbon atoms. ｝ 3. A benzene ring which may have a substituent other than X, a naphthalene ring which may have a substituent other than X, and a substituent other than X A pyridine ring optionally having a group, a pyridone ring optionally having a substituent other than X, a tetrahydroquinoline ring optionally having a substituent other than X, or a substituent other than X The metal chelate azomethine compound according to claim 1, which is a part of a pyrazole ring that may be substituted. 4. The residue B in the general formula [I] forms a benzene ring together with the two carbon atoms to which it is bonded, and at least 2
A group having an active hydrogen at the -position and an amino group represented by the following formula at the 4-position: (Wherein, R ¹⁴ and R ¹⁵ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or even represent an alkenyl group or a substituent cycloalkyl group which may have, or R ¹⁴ and R ¹⁵ are bonded to 5
It forms a six-membered or six-membered ring. The metal chelate azomethine compound according to claim 1 or 2, wherein 5. The group X having an active hydrogen in the general formula _{[I], -OH, -COOH, -SO 3 H} , -NHSO
₂ R ¹⁶ , -NHCOR ¹⁶ , -NHCOOR ¹⁶ (R ¹⁶ represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms which may have a substituent or a phenyl group which may have a substituent) The metal chelate azomethine compound according to any one of claims 1 to 4, which is selected from the group consisting of: 6. The metal chelate azomethine compound according to claim 1, wherein the optical recording medium has a recording layer on which information can be written and / or read by a laser on a substrate. An optical recording medium comprising: 7. The optical recording medium according to claim 6, wherein the metal of the metal chelate azomethine compound is a transition element. 8. The metal chelate azomethine compound according to claim 6, wherein the metal is cobalt or nickel.
An optical recording medium as described in the above. 9. The optical recording medium according to claim 6, wherein a reflective layer made of a metal and a protective layer made of a resin are provided on the recording layer.