JP2890687B2 - Azo metal chelate dye and optical recording medium using the dye - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a novel azo metal chelate dye of a bisazo compound and a metal, and an optical recording medium using the dye.

[Conventional technology]

In recent years, optical recording using a laser has been particularly developed in order to enable high-density information recording and storage and reproduction.

An example of the optical recording medium is an optical disk. 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 causing thermal deformation such as decomposition, evaporation, or dissolution in the recording layer at that location due to absorption of the irradiated laser light energy. Reproduction of recorded information is performed by reading the difference in reflectance between a portion where deformation has occurred and a portion where no deformation has occurred due to laser light.

Therefore, as an optical recording medium, it is necessary to efficiently absorb the energy of laser light, and a laser-absorbing dye is used.

Various types of optical recording media are known.

For example, Japanese Unexamined Patent Publication (Kokai) No. 55-97033 discloses a structure in which 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.
Furthermore, there is also a problem that the solubility in an organic solvent is extremely low, so that it cannot be used for coating by application.

Also, JP-A-58-112790, JP-A-58-114989, JP-A-59-11489
Nos. 85791 and 60-83236 disclose those in which a cyanine dye is provided in a recording layer. However, such dyes have a high solubility and can be coated by coating, but have a problem of poor light resistance. For this reason, Japanese Unexamined Patent Publication No. 59-55795 discloses a method of improving the light fastness by adding a quencher to this cyanine dye, but it is still at an insufficient level.

Regarding these problems, Japanese Patent Application Laid-Open No. 62-30090 discloses a complex of a monoazo compound and a metal as a medium having improved solubility in an organic solvent and light resistance. However, these compounds have problems that the photosensitive wavelength is short, the sensitivity is poor, and the storage stability under high temperature and high humidity is poor.

[Problems to be solved by the invention]

An object of the present invention is to provide an azo metal chelate dye of a bisazo compound and a metal which is excellent in sensitivity, storage stability and light resistance, and is suitable for spin coating, and an optical recording medium using the dye. It is.

[Means for solving the problem]

The present invention has the following general formula [I] (Wherein P and P ′ are each independently a 5- or 6-membered nitrogen-containing heterocyclic ring or a condensed ring of the nitrogen-containing heterocyclic ring and a benzene ring; B and B ′ are each independently R ¹ , R ² , R ¹ ′ and R ² ′ may each independently have a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, optionally substituted alkenyl or optionally substituted represents which may cycloalkyl group, X and X 'respectively are -OH,, -SH, -COOH, -SO 2 H,
_{-SO 3 H, -B (OH)} 2, -NH 2, -NHR, -PO (OH) 2,
-NHCOR or -NHSO ₂ R represents (wherein, R represents a optionally substituted alkyl group or a phenyl group), Y _{is, CH 2 n, CH 2 n} OCH 2 n, -OCH 2,
_{n O -, - OCH 2 n} OCH 2 n O -, - CH = CH-, CH 2
_n OCH _{2 n} , (Where n is an integer of 1 to 6). An azo metal chelate dye of a bisazo compound and a transition element metal represented by the formula (1) and an optical recording medium containing the dye in a recording layer.

Preferred bisazo compounds include compounds represented by the following general formula (I
I] (Wherein P ¹ and P ¹ ′ are each independently (Wherein ring A may have a substituent, M represents a hydrogen atom, an alkyl group, a halogen atom or an aryl group), and B and B ′ each independently represent a substituent R ¹ , R ² , R ¹ ′ and R ² ′ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, Represents an optionally substituted alkenyl group or an optionally substituted cycloalkyl group, X ¹ and X ¹ ′ each represent —COOH, —SO ₃ H or —OH, and Y represents CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2
n O -, - OCH 2 n} OCH 2 n O -, - CH = CH-, CH 2
_n OCH _{2 n} , (In the formula, n is an integer of 1 to 6.) And a more preferred compound is a compound represented by the following general formula [III]: (Wherein, rings A, A ′, B and B ′ may each independently have a substituent, and R ¹ , R ¹ ′, R ² and R ² ′ each independently represent a hydrogen atom, Represents an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted or a cycloalkyl group which may be substituted, and Y is CH _{2 n} , CH _{2 n} OCH
_{2 n, -OCH 2 n O -} , - OCH 2 n OCH 2 n O-,
_{-CH = CH-, CH 2 n OCH} 2 n, (Where n is an integer of 1 to 6). Or a bisazo compound represented by the following general formula [IV] (Wherein, rings A, A ′, B and B ′ may each independently have a substituent, and R ¹ , R ¹ ′, R ² and R ² ′ each independently represent a hydrogen atom, Represents an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted or a cycloalkyl group which may be substituted, and Y is CH _{2 n} , CH _{2 n} OCH
_{2 n, -OCH 2 n O -} , - OCH 2 n OCH 2 n O-,
_{-CH = CH-, CH 2 n OCH} 2 n, (Where n is an integer of 1 to 6). And a bisazo compound represented by the following formula:

 Hereinafter, the present invention will be described in detail.

The bisazo compound of the present invention is represented by the general formula [I], wherein P and P 'in the general formula [I] are 5
Alternatively, a nitrogen-containing heterocyclic ring that is a 6-membered ring or a condensed ring of the nitrogen-containing heterocyclic ring and a benzene ring may be used, and there is no particular limitation.

In the general formulas (I), (II), (III) and (IV), the substituents on the rings B and B ′ are nitro, cyano, alkyl, alkoxy, alkylsulfonyl, alkoxycarbonyl, thiocyanato Groups, perfluoroalkyl groups, halogen atoms and the like.

In the general formula [I], the general formulas [I], [II], [II
In I) and (IV), R ¹ , R ¹ ′, R ² and R ² ′ include a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, an aryl group, an alkenyl group or a cycloalkyl group; The groups may be substituted. Examples of the substituent include an alkoxy group, an alkoxyalkoxy group, an alkoxyalkoxyalkoxy group, an allyloxy group, an aryl group, an aryloxy group, a cyano group, a nitro group, a hydroxyl group, a tetrahydrofuryl group, an alkylsulfonylamino group, a halogen atom, and the like. Other examples of the substituent of the aryl group and the cycloalkyl group include an alkyl group and a vinyl group.

In the general formula [I], X is not particularly limited as long as it is a group having an active hydrogen. For example, -OH, -SH, -COOH,
_{-SO 2 H, -SO 3 H,} -B (OH) 2, -NH 2, -NHR, -PO (OH) 2,
—NHCOR (where R represents an alkyl group or a phenyl group which may be substituted), —NHSO ₂ R (where R is the same as defined above), and the like. Where X is -COOH, -S
When the group can be dissociated into anions such as O ₂ H,
When producing the azo metal chelate compound, it may be used as it is, or may be used in the form of a salt with a cation. As cations, inorganic cations such as Na ⁺ , Li ⁺ , K ⁺ or Organic cations.

In the general formula [II], examples of the substituent of ring A include an alkyl group, an alkoxy group, and a halogen atom.

In the general formulas (III) and (IV), rings A, A ′,
Examples of the substituent for B and B 'include a nitro group, a cyano group, an alkyl group, an alkoxy group, an alkylsulfonyl group, an alkoxycarbonyl group, a thiocyanato group, a perfluoroalkyl group, and a halogen atom.

Specific examples of the bisazo compound forming a chelate dye with a metal in the present invention include, for example, the following, which can be used alone or in combination of two or more.

In the present invention, as a metal forming a chelate dye with a bisazo compound, for example, Ni, Co, Fe, Ru, Rh, Pd, Os, Ir,
It is a transition element such as Pt, particularly preferably Ni or Co.

The general synthesis of the azo metal chelate dyes of the present invention is described, for example, in Furukawa; Analytica Chimica Acta 140 (1982) 281-28.
It can be performed according to the description in 9. For example, the general formula [V] (Wherein rings A, A ′ and Y are the same as defined above) by diazotizing the amino compound represented by the following general formula [VI] (Wherein, rings B, R ¹ and R ² are the same as defined above) to obtain a bisazo compound represented by the above general formula [III] by coupling with 2 equivalents of a substituted aniline carboxylic acid derivative represented by the following formula: The azo metal chelate dye of the present invention can be produced by reacting a bisazo compound with a metal salt in water and / or an organic solvent such as dioxane, tetrahydrofuran, acetone or ethanol.

The anion of the metal salt used in the preparation of the azo metal chelate _{^{dye, SCN -, SbF 6 -,}} Cl -, Br -, F -, ClO 4 -, BF 4 -, PF 6
_{^{-, CH 3 COO -, TiF}} 6 2-, SiF 6 2-, ZrF 6 2-, Monovalent or divalent anions are mentioned.

The optical recording medium of the present invention basically comprises a substrate and a recording layer containing a metal chelate dye of the bisazo compound, and further provides a sublayer on the substrate if necessary. be able to. As a preferable layer structure, a metal reflective layer such as aluminum or aluminum and a protective layer are provided on the recording layer to provide a medium with high reflectivity, and a write-once CD.
Can be media.

The substrate in the present invention may be either transparent or opaque to a laser beam to be used, and includes a support of a general recording material such as glass, plastic, paper, a plate-like or foil-like metal, and a plastic. Is preferred from various points. Plastics include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin,
Examples include polycarbonate resin, polyimide resin, epoxy resin, and polysulfone resin. Among these, an injection-molded polycarbonate resin substrate is particularly preferable in terms of high productivity, cost, and moisture absorption resistance.

The recording layer containing a chelate dye of a bisazo compound and a metal in the optical recording medium of the present invention has a film thickness of 100 to 5 mm.
μm, preferably 1000 ° to 3 μm.

The film can be formed by a generally used thin film forming method such as a vacuum evaporation method, a sputtering method, a doctor blade method, a casting method, a spinner method, and an immersion method, but from the viewpoint of mass productivity and cost, the spinner method is used. Is preferred.

Further, a binder can be used if necessary. Known binders such as polyvinyl alcohol, polyvinylpyrrolidone, ketone resin, nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate are used as the binder. In the case of film formation by the spinner method, the number of rotations is preferably 500 to 5000 rpm, and after spin coating, depending on the case, treatment such as heating or exposure to solvent vapor may be performed.

Further, in order to improve the stability and light resistance of the recording layer, a transition metal chelate compound (for example, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-
α-diketone). Further, other dyes can be used together if necessary. As the other dye, another kind of the same type of compound may be used, or a triarylmethane type dye, an azo dye, a cyanine type dye, a squarylium type dye, a metal complex of a monoazo compound, a Ni-indoaniline type dye, or the like. May be used.

As a coating solvent for forming the recording layer by a coating method such as a doctor blade method, a casting method, a spinner method, and an immersion method, particularly a spinner method, tetrafluoropropanol, octafluoropentanol, tetrachloroethane, bromoform, dibromoethane , Diacetone alcohol, ethyl cellosolve, xylene, 3-hydroxy-
Those having a boiling point of 120 to 160 ° C, such as 3-methyl-2-butanone, chlorobenzene, cyclohexanone, and methyl lactate, are preferably used.

Among these, for an injection molded polycarbonate resin substrate having excellent productivity, cost and moisture absorption resistance, diacetone alcohol and 3-hydroxy-3-methyl- are particularly preferable solvents that can be suitably used without damaging the substrate. 2-
Ketone alcohol solvents such as butanone; cellosolve solvents such as methyl cellosolve and ethyl cellosolve; perfluoroalkyl alcohol solvents such as tetrafluoropropanol and octafluoropentanol; methyl lactate;
And hydroxyester solvents such as methyl isobutyrate.

The recording layer of the optical recording medium of the present invention may be provided on both sides of the substrate, or may be provided only on one side.

Recording on the recording medium obtained as described above is performed by irradiating a laser beam, preferably a semiconductor laser beam, focused to about 1 μm on a recording layer provided on both sides or one side of the substrate. Thermal deformation of the recording layer, such as decomposition, evaporation, and melting, occurs due to absorption of laser energy in the portion irradiated with the laser light.

Reproduction of recorded information is performed by reading the difference in reflectance between a portion where thermal deformation has occurred and a portion where thermal deformation has not occurred using a laser beam.

Laser light used for the optical recording medium of the present invention is _{N 2, He-Cd, Ar} , He-Ne, ruby, semiconductor, but such a dye laser and the like, in particular, light weight, ease of handling, compactness A semiconductor laser is preferable from the viewpoint of properties and the like.

〔Example〕

Hereinafter, the present invention will be described specifically with reference to examples, but the present invention is not limited to the examples unless it exceeds the gist.

Example 1 9.35 g of ammonium thiocyanate and the following structural formula Was dissolved at room temperature in a mixed solution of 237.5 g of acetic acid and 12.5 g of water. 10 ℃ above solution
After cooling, a solution of 10 g of bromine dissolved in 25 g of acetic acid was added dropwise over 1 hour, and the mixture was further stirred at room temperature for 5 hours.

Next, after stirring the obtained reaction solution at 80 ° C. for 30 minutes, hot water
The mixture was added to 250 ml, stirred at 90 to 95 ° C. for 1 hour, and filtered while hot. The filtrate was cooled to room temperature, adjusted to pH 5 with sodium carbonate, separated by filtration and dried, and the following structural formula A pale yellow powder of a diaminothiazole compound represented by 4.46
g was obtained.

Physical properties Melting point: 217-219 ° C (decomposition) Mass spectrum: 312 (M ⁺ ), 279,252,209,183,163,136,1
03,63,39,27 The obtained diaminothiazole compound 2.50 g is phosphoric acid 50m
l, acetic acid 50 ml, dissolved in a mixed solution of propionic acid 16 ml,
Diazotization was carried out at 0-3 ° C. using 5.42 g of 45% nitrosylsulfuric acid. 2.64 g of 3-dimethylaminobenzoic acid and 0.2 g of urea
Was dissolved in 150 ml of methanol at 0 to 5 ° C., and the solution was neutralized with an aqueous ammonia solution.

The precipitated crystals are separated by filtration and dried to obtain the following structural formula 5.21 g of a black-green crystal of a bisazo compound represented by the formula was obtained.

0.30 g of the obtained bisazo compound was added to tetrahydrofuran 2
Dissolve in a mixed solution of 5 ml and water 25 ml, sodium acetate 0.07 g
And 0.14 g of nickel acetate were added. After stirring at room temperature for 1 hour, the precipitated crystal was separated by filtration and dried to obtain 0.22 g of a nickel chelate compound black crystal. The maximum inhalation wavelength (λ _max ) of the obtained compound in a chloroform solution is 552 nm and 58 nm.
It was 2 nm.

Example 2 (a) Compound Production Example Instead of the diamino compound used in Example 1, the following structural formula In the same manner as in Example 1 except that 5.3 g of the diamino compound represented by the following formula was used, the following structural formula A pale yellow powder of a diaminothiazole compound represented by 4.82
g was obtained.

Physical properties Melting point: (250 ° C. or more) Mass spectrum: 326 (M ⁺ ), 163,136,109,77,51 1.63 g of the obtained diaminothiazole compound was treated with phosphoric acid 16m
l, dissolved in a mixed solution of 16 ml of acetic acid and 5 ml of propionic acid.
Diazotization was carried out at 3.about-3 DEG C. with 3.39 g of 45% nitrosylsulfuric acid. A diazo solution obtained in a solution of 1.65 g of 3-dimethylaminobenzoic acid and 0.15 g of urea dissolved in 100 ml of methanol was added dropwise at 0 to 5 ° C., and neutralized with an aqueous ammonia solution. The precipitated crystals are separated by filtration and dried to obtain the following structural formula 2.28 g of a dark brown crystal of a bisazo compound represented by the following formula were obtained.

Λ _max (in a chloroform: methanol = 1: 1 solution) of the obtained compound was 602 nm and 642 nm.

0.30 g of the obtained bisazo compound was added to tetrahydrofuran 2
Dissolve in a mixed solution of 5 ml and water 25 ml, sodium acetate 0.07 g
And 0.14 g of nickel acetate were added. After stirring at room temperature for 1 hour, the precipitated crystals were separated by filtration and dried to obtain 0.23 g of black crystals of a nickel chelate compound.

The absorption spectrum data of the obtained compound (in a chloroform: methanol = 9: 1 solution) was as follows.

λ _max ; 602 nm, 642 nm Molecular absorption coefficient (ε); 14.1 × 10 ⁴ , 15.6 × 10 ⁴ (b) Recording medium production example 0.15 g of the nickel chelate compound of the bisazo compound obtained in the above compound production example was replaced with octafluoropentanol Five
g, and filtered through a 0.22 μm filter to obtain a solution. 5 ml of this solution is provided with a groove (group) having a depth of 700 mm and a width of 0.7 μm.
Inch) and applied at a rotation speed of 500 rpm by a spinner method. After the application, it was dried at 60 ° C. for 10 minutes. The λ _max of the coating film was 617 nm and 673 nm.

Next, on this coating film, by a sputtering method,
A gold film having a thickness of 2000 mm was formed to form a reflective layer. Further, an ultraviolet curable resin was spin-coated on the reflective layer, and then cured by irradiating ultraviolet rays to form a protective layer having a thickness of 10 μm.

(C) Example of optical recording While rotating the recording medium at 1.2 m / s, the center wavelength 78
Irradiate a 0 nm semiconductor laser beam with a recording power of 7.0 mW, and EF
M signal was recorded. Next, when this recording part was reproduced with a CD player having a semiconductor laser with a center wavelength of 780 nm,
A good reproduction signal was obtained.

In addition, light resistance (xenon fade meter accelerated test; 60 hours) and storage stability (70 ° C, 85% RH; 500 hours)
As a result of the test, the sensitivity and the reproduction signal were not deteriorated as compared with the initial stage, and the optical recording medium was extremely excellent.

Example 3 Using 1.63 g of the diaminothiazole compound obtained in the compound production example of Example 2, instead of 3-dimethylaminobenzoic acid of Example 1, 2.49 g of 3-dibutylaminobenzoic acid
The following structural formula was performed in the same manner as in Example 1 except that 2.96 g of a dark brown crystal of a bisazo compound represented by the following formula was obtained.

0.30 g of the obtained bisazo compound was added to tetrahydrofuran 2
Dissolve in a mixed solution of 5 ml and water 25 ml, sodium acetate 0.07 g
And 0.14 g of nickel acetate were added. After stirring at room temperature for 1 hour, the precipitated crystals were separated by filtration and dried to obtain 0.23 g of black crystals of a nickel chelate compound.

The absorption spectrum data of the obtained compound (in a chloroform: methanol = 9: 1 solution) was as follows.

λ _max ; 612 nm, 655 nm Molecular absorption coefficient (ε); 16.7 × 10 ⁴ , 20.1 × 10 ⁴ (b) Recording medium production example 0.15 g of the nickel chelate compound of the bisazo compound obtained in the above-mentioned complex production example was added to 5 g of diacetone alcohol. Dissolve,
The solution was filtered through a 0.22 μm filter to obtain a solution. 5 ml of this solution is provided with a groove (group) with a depth of 700 mm and a width of 0.7 μm,
The solution was dropped on an injection-molded polycarbonate resin substrate (diameter: 5 inches) and applied by a spinner method at a rotation speed of 500 rpm. After the application, it was dried at 60 ° C. for 10 minutes. The maximum absorption wavelengths of the coating film were 619 nm and 673 nm.

Next, on this coating film, by a sputtering method,
A gold film having a thickness of 2000 mm was formed to form a reflective layer. Further, an ultraviolet curable resin was spin-coated on the reflective layer, and then cured by irradiating ultraviolet rays to form a protective layer having a thickness of 10 μm.

(C) Example of optical recording While rotating the recording medium at 1.2 m / s, the center wavelength 78
Irradiate a 0 nm semiconductor laser beam with a recording power of 7.0 mW, and EF
M signal was recorded. Next, when this recording part was reproduced with a CD player having a semiconductor laser with a center wavelength of 780 nm,
A good reproduction signal was obtained.

In addition, light resistance (xenon fade meter accelerated test; 60 hours) and storage stability (70 ° C, 85% RH; 500 hours)
As a result of the test, the sensitivity and the reproduction signal were not deteriorated as compared with the initial stage, and the optical recording medium was extremely excellent.

〔The invention's effect〕

The metal chelate dye of the bisazo compound of the present invention has a high solubility in an organic solvent, can be coated by coating, and has good sensitivity, excellent light resistance and storage stability. An optical recording medium using is extremely useful.

[Brief description of the drawings]

FIG. 1 is a drawing showing a visible absorption spectrum of a nickel chelate compound of a bisazo compound obtained in Example 2 of the present invention, and FIG. 2 is a nickel chelate compound obtained in Example 2 of the present invention. FIG. 3 is a drawing showing an absorption spectrum of the coated thin film obtained in Example 2 of the present invention.

──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Toshio Kaneko 1000 Kamoshita-cho, Midori-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsubishi Chemical Research Institute (58) Field surveyed (Int.Cl. ⁶ , DB name) C09B 45 / 24 B41M 5/26 G11B 7/24 CA (STN) REG (STN)

Claims (9)

(57) [Claims] 1. The following general formula [I] (Wherein P and P ′ are each independently a 5- or 6-membered nitrogen-containing heterocyclic ring or a condensed ring of the nitrogen-containing heterocyclic ring and a benzene ring; B and B ′ are each independently R ¹ , R ² , R ¹ ′ and R ² ′ may each independently have a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, X represents an alkenyl group which may be substituted, or a cycloalkyl group which may be substituted; X and X ′ each represent —OH, —SH, —COOH, —SO ₂ H,
_{SO 3 H, -B (OH)} 2, -NH 2, -NHR, -PO (OH) 2, -
NHCOR or —NHSO ₂ R (where R represents an optionally substituted alkyl group or a phenyl group), and Y represents CH _{2 n} , CH _{2 n} OCH _{2 n} , —OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (Where n is an integer of 1 to 6). An azo metal chelate dye of a bisazo compound represented by the formula and a transition element metal. 2. A bisazo compound represented by the following general formula [II]: (Wherein P ¹ and P ¹ ′ are each independently (Wherein ring A may have a substituent, M represents a hydrogen atom, an alkyl group, a halogen atom or an aryl group), and B and B ′ each independently represent a substituent R ¹ , R ² , R ¹ ′ and R ² ′ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, Represents an optionally substituted alkenyl group or an optionally substituted cycloalkyl group, X ¹ and X ¹ ′ each represent —COOH, —SO ₃ H or —OH, and Y represents CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (In the formula, n is an integer of 1 to 6.) The azo metal chelate dye according to claim 1, wherein the dye is represented by the following formula: 3. A bisazo compound represented by the following general formula [III]: (Wherein, rings A, A ′, B and B ′ may each independently have a substituent, and R ¹ , R ¹ ′, R ² and R ² ′ each independently represent a hydrogen atom, Represents an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted or a cycloalkyl group which may be substituted; Y is CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (Where n is an integer of 1 to 6). The azo metal chelate dye according to claim 1, wherein the dye is represented by the following formula: 4. A bisazo compound represented by the following general formula [IV]: (Wherein, rings A, A ′, B and B ′ may each independently have a substituent, and R ¹ , R ¹ ′, R ² and R ² ′ each independently represent a hydrogen atom, Represents an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted or a cycloalkyl group which may be substituted; Y is CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (Where n is an integer of 1 to 6). The azo metal chelate dye according to claim 1, wherein the dye is represented by the following formula: 5. An optical recording medium having a recording layer on which information can be written and / or read by a laser on a substrate, wherein the recording layer has the following general formula [I]: (Wherein P and P ′ are each independently a 5- or 6-membered nitrogen-containing heterocyclic ring or a condensed ring of the nitrogen-containing heterocyclic ring and a benzene ring; B and B ′ are each independently R ¹ , R ² , R ¹ ′ and R ² ′ may each independently have a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, X represents an alkenyl group which may be substituted, or a cycloalkyl group which may be substituted; X and X ′ each represent —OH, —SH, —COOH, —SO ₂ H,
_{SO 3 H, -B (OH)} 2, -NH 2, -NHR, -PO (OH) 2, -
NHCOR or —NHSO ₂ R (where R represents an optionally substituted alkyl group or a phenyl group), and Y represents CH _{2 n} , CH _{2 n} OCH _{2 n} , —OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (Where n is an integer of 1 to 6). An optical recording medium characterized by containing an azo metal chelate dye of a bisazo compound represented by the formula (1) and a transition element metal. 6. A bisazo compound represented by the following general formula [II]: (Wherein P ¹ and P ¹ ′ are each independently (Wherein ring A may have a substituent, M represents a hydrogen atom, an alkyl group, a halogen atom or an aryl group), and B and B ′ each independently represent a substituent R ¹ , R ² , R ¹ ′ and R ² ′ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, Represents an optionally substituted alkenyl group or an optionally substituted cycloalkyl group, X ¹ and X ¹ ′ each represent —COOH, —SO ₃ H or —OH, and Y represents CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (In the formula, n is an integer of 1 to 6.) The optical recording medium according to claim 5, characterized by: 7. A bisazo compound represented by the following general formula [III]: (Wherein, rings A, A ′, B and B ′ may each independently have a substituent, and R ¹ , R ¹ ′, R ² and R ² ′ each independently represent a hydrogen atom, Represents an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted or a cycloalkyl group which may be substituted; Y is CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (In the formula, n is an integer of 1 to 6.) The optical recording medium according to claim 5, wherein: 8. A bisazo compound represented by the following general formula [IV]: (Wherein, rings A, A ′, B and B ′ may each independently have a substituent, and R ¹ , R ¹ ′, R ² and R ² ′ each independently represent a hydrogen atom, Represents an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted or a cycloalkyl group which may be substituted; Y is CH _{2 n} , CH _{2 n} OCH _{2 n,} -OCH _{2 n} O
_{-, - OCH 2 n OCH 2} n O -, - CH = CH-, CH 2 n
OCH _{2 n} , (In the formula, n is an integer of 1 to 6.) The optical recording medium according to claim 5, wherein: 9. The method according to claim 5, wherein a metal reflective layer and a protective layer are provided on the recording layer.
Item 14. The optical recording medium according to any one of the above items.