JP2001271001A - Azo-based coloring matter and optical recording medium using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a coloring matter suitable as an optical recording medium especially suitable for reproducing records with semiconductor laser beams at a short wavelength. SOLUTION: This azo-based coloring matter is represented by general formula (1) [ring A denotes an aromatic ring containing a heterocyclic ring and a condensed ring; X denotes a group containing an active hydrogen; Y denotes O, S or NR3 (R3 denotes hydrogen or an alkyl group); and R1 and R2 denote each independently hydrogen, a hydrocarbon group which may have a substituent group, a heterocyclic group which may have a substituent group, NR4R5, OR6 or SR7 (R4 to R7 denote each hydrogen or an optional substituent group)].

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 wavelengths of 780 nm,
There is a demand for an optical recording medium that can perform high-density recording and reproduction with a laser beam having a wavelength shorter than 830 nm. Conventionally proposed optical recording media include magneto-optical recording media, phase-change recording media, chalcogen oxide optical recording media, organic dye-based optical recording media, and the like. It is considered to be superior in that it is inexpensive in terms of cost and the manufacturing process is easy.

At present, organic dye-based optical recording media include:
CD-Rs of a type in which a metal layer having a high reflectivity is laminated on an organic dye layer are mass-produced and widely known.
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 / reproducing -R has also been developed and put into practical use.
However, as shorter wavelength laser oscillation becomes possible, there is an increasing need for an optical recording medium capable of recording and reproducing with a shorter wavelength laser, ie, a blue semiconductor laser (wavelength: 350 nm to 530 nm).

[0004]

Generally, an optical recording medium used as a CD-R or a DVD-R has a low reflectance with respect to a blue semiconductor laser beam having a short wavelength, and recording and reproduction cannot be performed with the laser beam. Have a problem.

An object of the present invention is to provide an organic dye-based optical recording medium which can be recorded and reproduced by a blue semiconductor laser.

[0006]

The azo dye of the present invention comprises:
It has a structure represented by the following general formula (1).

[0007]

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(In the formula (1), ring A is an aromatic ring having a broad meaning including a heterocyclic ring and a condensed ring, X represents a group having an active hydrogen, and Y represents O, S or NR ₃ (R ₃ Represents a hydrogen or an alkyl group), and R ₁ and R ₂ each independently represent a hydrogen atom, a hydrocarbon group optionally having a substituent, a heterocyclic group optionally having a substituent, —NR ₄ R ₅ , —OR _6, or —SR ₇ (where R ₄ , R ₅ , R ₆ , and R ₇ each represent a hydrogen atom or an arbitrary substituent).

That is, the present inventors have found that the use of, for example, a compound represented by the following general formula in an azo dye as a coupling component shifts the absorption maximum value of the dye to a shorter wavelength side. I paid attention.

[0010]

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(Wherein G ₁ and G ₂ are each independently O,
Represents a group that is π-bonded to the carbon atom to which it is bonded, such as S or NR, and R ₁ and R ₂ each independently represent a hydrogen atom, a hydrocarbon group, a heterocyclic group, -NRR′-, -OR,- Represents SR or the like (R and R 'are arbitrary). )

An azo dye having a specific structure obtained from a specific diazo component and a coupling component is difficult to crystallize and has an absorption maximum in a short wavelength region. It has been found that an optical recording medium corresponding to a blue semiconductor laser can be suitably obtained, and the present invention has been completed.

The azo dyes of the present invention include, for example, monoazo dyes represented by the general formula (1).

The monoazo dye obtained from the specific diazo component and the coupling component is hardly crystallized and has an absorption maximum in a short wavelength region. Therefore, by using this in a recording layer, optical recording corresponding to a blue semiconductor laser can be performed. A medium is suitably obtained.

In the monoazo dye, as the ring A, a benzene ring which may have a substituent in addition to the azo group, or an oxazole ring, a pyrazole ring, an imidazole ring, a thiadiazole ring, an isoxazole ring or a triazole ring; Preferably, a benzene ring is used.

The azo dye of the present invention may be a metal azo chelate dye comprising a compound represented by the following formula (2) or (3) and a metal.

[0017]

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(In the formulas (2) and (3), rings A-1 and A-
2 represents a heteroaromatic ring formed together with a carbon atom and a nitrogen atom to which it is bonded, and X, Y, R ₁ and R ₂ have the same meanings as in the general formula (1). )

By using a specific structure as a coupling component of an azo compound, the metal azo-based chelate dye shifts the maximum absorption value to a shorter wavelength side and is difficult to crystallize by complexation, and is suitable for a blue semiconductor laser. It is effective as a recording layer of an optical recording medium to be used.

In the metal azo-based chelate dye, the rings A-1 and A-2 are particularly preferably an oxazole ring, a pyrazole ring, an imidazole ring, a thiadiazole ring, an isoxazole ring or a triazole ring.

In the azo dye of the present invention, at least one of R ₁ and R _{2 in} the general formulas (1) to (3) contains a cyclic hydrocarbon group which may have a substituent. It is preferably a group or a group containing a heterocyclic ring which may have a substituent.

The optical recording medium of the present invention is an optical recording medium in which a recording layer capable of recording or reproducing information by laser is provided on a substrate, wherein the recording layer contains such an azo dye of the present invention. It is characterized by doing.

In the optical recording medium of the present invention, the laser wavelength for recording or reproducing information is preferably 350 nm to 530 nm.

[0024]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.

The azo dye of the present invention having the structure represented by the above general formula (1) is 350 to 530 nm.
Dyes having an absorption in the blue light region and suitable for recording with a blue laser are preferred.

As described above, the azo dye may be a metal azo chelate dye which is difficult to crystallize by forming a complex, or may be a monoazo dye represented by the general formula (1). May be.

That is, in general, a monoazo dye is a complex dye composed of the monoazo dye and a metal (metal-containing azo chelate dye).
This is considered to be unfavorable because it is more likely to crystallize when used for the recording layer of an optical recording medium as compared with. Therefore, in this respect, metal azo chelate dyes are excellent. However, metal-containing azo-based chelate dyes tend to shift the absorption maximum to longer wavelengths due to complexation, and it may be difficult to obtain an optical recording medium suitable for recording / reproducing at short wavelengths. In some cases, a simple (uncomplexed) monoazo dye may make it easier to obtain a dye having an absorption maximum at a short wavelength.

In the general formula (1), the ring A is an aromatic ring in a broad sense including a heterocyclic ring and a condensed ring, and the azo dye of the present invention is represented by the general formula (2) or (3). In the case of a metal azo chelate dye of a compound and a metal represented by
Rings A-1 and A-2 may be any heteroaromatic ring formed with the carbon and nitrogen atoms to which they are attached,
Although not limited, the following are preferred.

[0029]

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(Wherein D _{1 to} D ₄₂ are each independently a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec.
A straight-chain or branched alkyl group having 1 to 6 carbon atoms such as -butyl group, n-pentyl group, n-hexyl group, trifluoromethyl group, pentafluoroethyl group, 2-fluoroethyl group, 2,2-difluoro Ethyl group, 2,2,2-trifluoroethyl group, 2H-tetrafluoroethyl group, heptafluoro-n-propyl group, 3,3,3-trifluoropropyl group, 1H, 1H-pentafluoropropyl group, 1H , 1H, 3H-tetrafluoropropyl group, perfluoro-n-butyl group, 1H, 1H-pentafluorobutyl group, 1H, 1H, 3H-hexafluorobutyl group, perfluoro-n-bentyl group, 1H, 1H, 5H
A straight-chain fluorinated alkyl group having 1 to 6 carbon atoms such as -octafluoropentyl group, perfluoro-n-hexyl group, 2- (perfluorobutyl) ethyl group; 1- (trifluoromethyl) tetrafluoroethyl group , 1- (trifluoromethyl) -2,2,2-trifluoroethyl group, 1-
(Trifluoromethyl) ethyl group, 1- (difluoromethyl) -2,2-difluoroethyl group, 1- (fluoromethyl) -2-fluoroethyl group, perfluoro-1,
1-dimethylethyl group, 1,1-di (trifluoromethyl) ethyl group, 1- (trifluoroethyl) -1-methylethyl group, 1-methyl-1H-perfluoropropyl group, 1-methyl-1H- Perfluorobutyl group, 2,2
-Di (trifluoromethyl) propyl group, 2-methyl-
4,4,4-trifluorobutyl group, perfluoro-3
A branched fluorinated alkyl group having 1 to 6 carbon atoms such as -methylbutyl group, 2- (perfluoro-1-methylethyl) ethyl group, 3- (perfluoro-1-methylethyl) propyl group; trifluoromethoxy group Pentafluoromethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2H
A tetrafluoroethoxy group, a heptafluoro-n-propoxy group, a 3,3,3-trifluoropropoxy group,
1H, 1H-pentafluoropropoxy group, 1H, 1H
-3H-tetrafluoropropoxy group, perfluoro-
n-butoxy group, 1H, 1H-heptafluorobutoxy group, 1H, 1H, 3H-hexafluorobutoxy group, perfluoro-n-pentyloxy group, 1H, 1H, 5H
-Octafluoropentyloxy group, perfluoro-n
A straight-chain fluorinated alkoxy group having 1 to 6 carbon atoms, such as -hexyloxy group or 2- (perfluorobutyl) ethoxy group;
1- (trifluoromethyl) tetrafluoroethoxy group, 1- (trifluoromethyl) -2,2,2-trifluoroethoxy group, 1- (trifluoromethyl) ethoxy group, 1- (difluoromethyl) -2, 2-difluoroethoxy group, 1- (fluoromethyl) -2-fluoroethoxy group, perfluoro-1,1-dimethylethoxy group, 1,1-di (trifluoromethyl) ethoxy group, 1
-(Trifluoroethyl) -1-methylethoxy group, 1
-Methyl-1H-perfluoropropoxy group, 1-methyl-1H-perfluorobutoxy group, 2,2-di (trifluoromethyl) propoxy group, 2-methyl-4,4,
1 to 6 carbon atoms such as a 4-trifluorobutoxy group, a perfluoro-3-methylbutoxy group, a 2- (perfluoro-1-methylethyl) ethoxy group, and a 3- (perfluoro-1-methylethyl) propoxy group. A cyclic fluorinated alkoxy group; a cyclic alkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group; a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n- Butoxy group, tert-
C1-C6 alkoxy groups such as butoxy group, sec-butoxy group, n-pentyloxy group, n-hexyloxy group; acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group , A hexanoyl group, a heptanoyl group or the like having 2 to 7 carbon atoms
An alkylcarbonyl group having 2 to 2 carbon atoms such as a vinyl group, a propenyl group, a butenyl group, a pentenyl group and a hexenyl group;
6 linear or branched alkenyl groups; cyclic alkenyl groups having 3 to 6 carbon atoms such as cyclopentenyl and cyclohexenyl; halogen atoms such as fluorine, chlorine and bromine; formyl; hydroxyl; ;
1 carbon atom such as hydroxymethyl group, hydroxyethyl group
To 6 hydroxyalkyl groups; methoxycarbonyl groups,
An ethoxycarbonyl group, an n-propoxycarbonyl group,
Isopropoxycarbonyl group, n-butoxycarbonyl group, tert-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, n
An alkoxycarbonyl group having 2 to 7 carbon atoms such as a hexyloxycarbonyl group; a nitro group; a cyano group;
C1-C10 such as methylamino, ethylamino, n-propylamino, n-butylamino, dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, etc. Alkylamino group; methoxycarbonylmethyl group, methoxycarbonylethyl group, ethoxycarbonylmethyl group, ethoxycarbonylethyl group, n-propoxycarbonylethyl group, n-propoxycarbonylpropyl group, isopropoxycarbonylmethyl group, isopropoxycarbonylethyl group, etc. C3 to C7 alkoxycarbonylalkyl group; methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, tert-butylthio group, sec-butylthio group, n-pentylthio group, n
An alkylthio group having 1 to 6 carbon atoms such as -hexylthio group;
A trifluoromethylthio group, a pentafluoroethylthio group, a 2-fluoroethylthio group, a 2,2-difluoroethylthio group, a 2,2,2-trifluoroethylthio group,
2H-tetrafluoroethylthio group, heptafluoro-
n-propylthio group, 3,3,3-trifluoropropylthio group, 1H, 1H-pentafluoropropylthio group, 1H, 1H, 3H-tetrafluoropropylthio group, perfluoro-n-butylthio group, 1H, 1H -Pentafluorobutylthio group, 1H, 1H, 3H-hexafluorobutylthio group, perfluoro-n-bentylthio group, 1H, 1H, 5H-octafluoropentylthio group, perfluoro-n-hexylthio group, 2- ( C1-C6 linear fluorinated alkylthio group such as perfluorobutyl) ethylthio group; 1- (trifluoromethyl)-
Tetrafluoroethylthio group, 1- (trifluoromethyl) -2,2,2-trifluoroethylthio group, 1-
(Trifluoromethyl) ethylthio group, 1- (difluoromethyl) -2,2-difluoroethylthio group, 1-
(Fluoromethyl) -2-fluoroethylthio group, perfluoro-1,1-dimethylethylthio group, 1,1-di (trifluoromethyl) ethylthio group, 1- (trifluoroethyl) -1-methylethylthio Group, 1-methyl-
1H-perfluoropropylthio group, 1-methyl-1H
-Perfluorobutylthio group, 2,2-di (trifluoromethyl) propylthio group, 2-methyl-4,4,4-
1 to 6 carbon atoms such as a trifluorobutylthio group, a perfluoro-3-methylbutylthio group, a 2- (perfluoro-1-methylethyl) ethylthio group, and a 3- (perfluoro-1-methylethyl) propylthio group. A branched alkylfluorthio group; methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, sec-butylsulfonyl, n-pentylsulfonyl, C1-C6 alkylsulfonyl group such as n-hexylsulfonyl group; trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, 2-fluoroethylsulfonyl group, 2,2-difluoroethylsulfonyl group, 2,2,2 -Trifluoroethylsulfonyl group, 2H-tetra Fluoro ethylsulfonyl group, heptafluoro--n- propylsulfonyl group, 3,3,3
-Trifluoropropylsulfonyl group, 1H, 1H-pentafluoropropylsulfonyl group, 1H, 1H, 3H
-Tetrafluoropropylsulfonyl group, perfluoro-n-butylsulfonyl group, 1H, 1H-heptafluorobutylsulfonyl group, 1H, 1H, 3H-hexafluorobutylsulfonyl group, perfluoro-n-pentylsulfonyl group, 1H, 1H Linear alkylsulfonyl group having 1 to 6 carbon atoms, such as 1,5H-octafluoropentylsulfonyl group, perfluoro-n-hexylsulfonyl group, 2- (perfluorobutyl) ethylsulfonyl group; 1- (trifluoro Methyl) tetrafluoroethylsulfonyl group, 1- (trifluoromethyl) -2,2,2
2-trifluoroethylsulfonyl group, 1- (trifluoromethyl) ethylsulfonyl group, 1- (difluoromethyl) -2,2-difluoroethylsulfonyl group, 1-
(Fluoromethyl) -2-fluoroethylsulfonyl group, perfluoro-1,1-dimethylethylsulfonyl group, 1,1-di (trifluoromethyl) ethylsulfonyl group, 1- (trifluoroethyl) -1-methylethyl Sulfonyl group, 1-methyl-1H-perfluoropropylsulfonyl group, 1-methyl-1H-perfluorobutylsulfonyl group, 2,2-di (trifluoromethyl) propylsulfonyl group, 2-methyl 4,4,4- Trifluorobutylsulfonyl group, perfluoro-3-methylbutylsulfonyl group, 2- (perfluoro-1-methylethyl) ethylsulfonyl group, 3- (perfluoro-1-
1-6 carbon atoms such as methylethyl) propylsulfonyl group
A branched alkyl fluoride sulfonyl group; an aryl group having 6 to 16 carbon atoms which may have a substituent; an arylcarbonyl group having 7 to 17 carbon atoms which may have a substituent;
_{-CD 43 = C (CN) D} 44 (D 43 represents a hydrogen atom, or wherein D ₁ to D ₄₂ similar to carbon atoms as defined in 1-6
Wherein D ₄₄ is a cyano group or the aforementioned D ₁ to
It represents alkoxycarbonyl groups were analogous to those of 2-7 carbon atoms defined in the D _42. ). Further, among D _{1 to} D ₄₂ , adjacent groups are bonded to each other to form a ring A-1.
Alternatively, a ring fused to A-2 may be formed. )

Substituents D ₁ to A-1 and A-2 for the rings A-1 and A-2
Preferred groups among those mentioned as D ₄₂ is somewhat different depending on the structure of the ring A-1 and A-2, a hydrogen atom, an unsubstituted or halogenated alkyl group, unsubstituted or halogenated alkylthio group, no It is a substituted or halogenated alkoxy group, aldehyde group, cyano group, nitro group or halogen atom.

Of the above-mentioned 17 kinds of rings exemplified as ring A-1 or ring A-2, more preferred are the following 10 kinds of oxazole rings, pyrazole rings, imidazole rings, thiadiazole rings, isoxazole rings or triazoles. It is a ring.

[0033]

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When the azo dye of the present invention is a monoazo dye represented by the general formula (1), the ring A may be a plurality of rings or a condensed ring, but is suitable for optical recording at a wavelength of 350 to 530 nm. It is preferably a monocyclic ring from the viewpoint of having the maximum absorption wavelength, and particularly, 10 kinds of oxazole ring, pyrazole ring, imidazole ring, thiadiazole ring, isoxazole ring or triazole ring represented by the above formula 7, or benzene ring Particularly, a benzene ring is preferable.

The ring A of the monoazo dye may have a substituent other than the azo group.

As such a substituent, for example, a methyl group,
Ethyl group, propyl group, isopropyl group, n-butyl
Group, sec-butyl group, tert-butyl group, n-heptane
C1-C18 linear or branched alkyl such as a tyl group
Group; cyclopropyl group, cyclopentyl group, cyclohexyl
Cyclic alkyl having 3 to 18 carbon atoms such as a sil group and an adamantyl group
Kill group; charcoal such as vinyl group, propenyl group and hexenyl group
A linear or branched alkenyl group having a prime number of 2 to 18;
Having 3 to 18 carbon atoms such as an ethenyl group and a cyclohexenyl group;
Cyclic alkenyl group; acetyl group, propionyl group, butyric
Ryl group, isobutyryl group, valeryl group, isovaleryl group
Linear or branched alkyl carbonyl having 2 to 18 carbon atoms, such as
A methoxy group, an ethoxy group, an n-propoxy group,
Sopropoxy group, n-butoxy group, sec-butoxy
Group, tert-butoxy group, etc.
Is a branched alkoxy group; propenyloxy group, butenyl
A straight-chain having 3 to 18 carbon atoms such as an oxy group and a pentenyloxy group;
Chain or branched alkenyloxy group; methylthio group, ethyl
Luthio group, n-propylthio group, n-butylthio group, s
carbon such as ec-butylthio group and tert-butylthio group
A linear or branched alkylthio group of the formulas 1 to 18;
Oromethyl group, pentafluoroethyl group, heptafluor
B-n-propyl group, heptafluoroisopropyl group,
Perfluoro-n-butyl group, perfluoro-sec-
Carbon such as butyl group and perfluoro-tert-butyl group
A linear or branched fluoroalkyl group of the formulas 1 to 18;
Fluoromethoxy group, pentafluoroethoxy group, hept
Tafluoro-n-propoxy group, heptafluoroisop
Loxy group, perfluoro-n-butoxy group, perful
Oro-sec-butoxy group, perfluoro-tert-
A linear or branched fluoro group having 1 to 18 carbon atoms such as butoxy group
Lower alkoxy group; trifluoromethylthio group, pentaf
Fluoroethylthio group, heptafluoro-n-propylthio
O group, heptafluoroisopropylthio group, perfluoro
Low-n-butylthio group, perfluoro-sec-butyl
Charcoal such as thio group, perfluoro-tert-butylthio group, etc.
Linear or branched fluoroalkylthio having 1 to 18 primes
Groups; halogen atoms such as fluorine, chlorine and bromine atoms
Nitro group; cyano group; hydroxy group; formyl group;
Sulfonic acid group; carboxyl group; -NR₈R₉Represented by
Amino group; -NHCOR_TenAcylamino represented by
Group; -NHCOOR₁₁A carbamate group represented by the formula:
HSO_TwoR ₁₂A sulfonamide group represented by the formula: -COOR
₁₃A carboxylic ester group represented by the formula: -CONR₁₄R_Fifteen
A carbamoyl group represented by the formula:_TwoNR₁₆R₁₇Represented by
Sulfamoyl group; -SO_ThreeR₁₈Sulfo represented by
And acid ester groups.

Here, R _{8 to} R ₁₈ each represent a hydrogen atom, a linear or branched alkyl group which may be substituted, a cyclic alkyl group which may be substituted, an alkenyl group which may be substituted, or a substituent. Represents a cyclic alkenyl group or an optionally substituted phenyl group. The substituent has 1 to 1 carbon atoms.
Examples of the substituent such as a chain alkyl group having 8 or a cyclic alkyl group having 3 to 18 carbon atoms include the same groups as described below.

The position and number of substituents other than the azo group in ring A are not particularly limited. When it has a plurality of substituents, they may be the same or different.

Of these, a linear or branched alkyl group having 1 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, a linear or branched alkenyl group having 2 to 18 carbon atoms,
To 18 cyclic alkenyl groups may be further substituted. Such “further substituents” include, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert
An alkoxy group having 1 to 10 carbon atoms such as a butoxy group; a methoxymethoxy group, an ethoxymethoxy group, a propoxymethoxy group, an ethoxyethoxy group, a propoxyethoxy group,
An alkoxyalkoxy group having 2 to 12 carbon atoms such as methoxybutoxy group; a carbon atom having 3 carbon atoms such as alkoxyalkoxyalkoxy group such as methoxymethoxymethoxy group, methoxymethoxyethoxy group, methoxyethoxymethoxy group, methoxymethoxyethoxy group, ethoxyethoxymethoxy group and the like. ~
15 alkoxyalkoxyalkoxy groups; allyloxy groups; 6 carbon atoms such as phenyl, tolyl, and xylyl groups
To 12 aryl groups (these may be further substituted with a substituent); and 6 to 12 carbon atoms such as a phenoxy group, a tolyloxy group, a xylyloxy group, and a naphthyloxy group.
Aryloxy group; alkenyloxy group having 2 to 12 carbon atoms such as allyloxy group and vinyloxy group; cyano group;
Nitro group; hydroxyl group; tetrahydrofuryl group; amino group; alkylamino group having 1 to 10 carbon atoms such as N, N-dimethylamino group, N, N-diethylamino group; methylsulfonylamino group, ethylsulfonylamino group, n
An alkylsulfonylamino group having 1 to 6 carbon atoms such as -propylsulfonylamino group; a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, C2-C7 alkoxycarbonyl groups such as n-butoxycarbonyl; C2-C7 alkoxy groups such as methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, isopropylcarbonyloxy and n-butylcarbonyloxy; An alkylcarbonyloxy group of 7; a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an isopropoxycarbonyloxy group, an n-butoxycarbonyloxy group, or the like;
And the like.

A cyclic alkyl group having 3 to 18 carbon atoms,
And a cyclic alkenyl group having 3 to 18 carbon atoms is a methyl group,
Even if it is substituted with a linear or branched alkyl group having 1 to 18 carbon atoms such as an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group and an n-heptyl group. Good.

As a substituent of the benzene ring of the ring A, a chain alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a fluoroalkyl group having 1 to 6 carbon atoms, and a carbon atom having 1 to 10 carbon atoms are preferable. Cyclic alkyl group, C1-6 fluoroalkoxy group, C1-6 fluoroalkylthio group, halogen atom, nitro group, cyano group, -NR
_{31 R 32, -NHCOR 33, -SO} 2 NR 34 R 35, -NH
SO ₂ R ₃₆ and —COOR ₃₇ (where R _{31 to} R ₃₇ each independently represent an alkyl group or an aryl group). Particularly preferably, an alkyl group, fluoroalkyl group, a halogen atom, a nitro group, -COOR _37, and the like.

The number of substituents other than the azo group in the ring A is preferably 1 to 3, more preferably 1 or 2. Also, in order to suppress crystallization of the monoazo dye,
The ring A preferably has a relatively bulky substituent, and in the case of an alkyl group or an alkoxy group, a branched or substituted one with a halogen atom, or a cyclic one is preferred. From the viewpoint of bulkiness, a halogen atom is also preferable.

X represents a hydroxyl group, an amino group,
Examples thereof include groups having active hydrogen such as a sulfonic acid group, a carboxyl group, an alkylsulfonamino group, and a thiol group, and a hydroxyl group is particularly preferable.

Y represents O, S or NR ₃ (R ₃ is a hydrogen atom or an alkyl group), and O is particularly preferred.

R ₁ and R ₂ are each independently a hydrogen atom; a hydrocarbon group which may be substituted; a heterocyclic group which may be substituted; --NR ₄ R ₅ ; --OR ₆ ; --SR ₇ (where R _{4 to} R
₇ is a hydrogen atom or an optional substituent).

Examples of the unsubstituted hydrocarbon group include the aforementioned linear or branched alkyl group having 1 to 18 carbon atoms;
A cyclic alkyl group of 18; an aryl group having 6 to 18 carbon atoms;
Examples thereof include a linear or branched alkenyl group having 2 to 18 carbon atoms. Among these, a linear or branched alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 12 carbon atoms are more preferable.

These are those having 1 to 1 carbon atoms which are substituents of ring A.
It may be substituted with various substituents described above as “further substituents” such as a chain alkyl group of 18.

The unsubstituted heterocyclic group is preferably a 4- to 8-membered ring, for example, the following rings.

[0049]

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(Wherein Z represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms)

Each of these rings may have a substituent. Among them, those substituted or unsubstituted with an alkyl group or a halogenated alkyl group are preferred.

R _{4 to} R ₇ are a hydrogen atom or an arbitrary substituent, and the substituent is not particularly limited, but rather is a monoazo-based compound composed of the compound represented by the general formula (1), rather than a group having such a large molecular weight. The substituent is preferably such that the molecular weight of the entire dye is 800 or less, and the molecular weight of the metal azo-based chelate dye of the compound represented by formula (2) or (3) and a metal is 2000 or less.

As specific groups, for example, R ₄ and R ₅ include the same substituents as R ₁ and R _2, and among them, preferred are one having a hydrogen atom and the other having a carbon atom. A linear or branched alkyl group having 1 to 10 carbon atoms; a linear or branched alkyl group having 1 to 10 carbon atoms, which may be substituted with an aryl group having 6 to 12 carbon atoms; A linear or branched alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 12 carbon atoms which may be substituted;

R ₆ and R ₇ are the same as R ₁ and R ₂ ,
Preferred are a linear or branched alkyl group having 1 to 10 carbon atoms; an alkyl group having 1 to 10 carbon atoms which is substituted by halogen; and a carbon number substituted with an aryl group having 6 to 12 carbon atoms which may be substituted. 1-10 linear or branched alkyl groups;
It is an aryl group having 6 to 12 carbon atoms.

It should be noted that the ease of synthesis of the dye and the wavelength 3
From the viewpoint of an absorption wavelength suitable for an optical recording medium capable of suitably performing recording and reproduction with a laser beam of 50 to 530 nm,
At least one of R ₁ and R ₂ is preferably a group containing a cyclic hydrocarbon group which may have a substituent, or a group containing a heterocyclic ring which may have a substituent.

[0056] Here, "group containing a cyclic hydrocarbon group", in addition to the aryl group, in which a part of the linear or branched alkyl group is substituted with a cyclic hydrocarbon group, R ₄ ~ R
_The same applies to the “group containing a heterocyclic ring”, including those having a cyclic hydrocarbon group (aryl group) as any one of ₇ above.

In the present invention, specific examples of the monoazo dye comprising the compound represented by formula (1) include the following.

[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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In the metal azo chelate dye of the compound represented by formula (2) or (3) and a metal, preferred examples of the compound include the following.

[When Rings A-1 and A-2 are Oxazole Rings]

[0065]

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[When the rings A-1 and A-2 are pyrazole rings]

[0067]

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[When Rings A-1 and A-2 are Imidazole Rings]

[0069]

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[When the rings A-1 and A-2 are isoxazole rings]

[0071]

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[When rings A-1 and A-2 are thiadiazole rings]

[0073]

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[When Rings A-1 and A-2 are Triazole Rings]

[0075]

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In the metal azo-based chelate dye of the present invention, various metals capable of forming a complex can be used as the metal which forms the azo compound and the chelate, but the transition metal is preferred because of its good absorption spectrum shape. Particularly, Ni, Co, Cu, Fe, Zn, Pd and the like are preferable.

The monoazo dyes and metal azo chelate dyes of the present invention are excellent in thin film forming properties when, for example, forming a recording layer from a solution containing the dyes. Very useful as a dye for use in the layer.

Further, the monoazo dye and the metal azo chelate dye of the present invention have a recording layer containing the dye in a shorter wavelength region (350 nm to 500 nm) having an absorption of a strength suitable for recording / reproducing by a laser beam. Therefore, it is extremely useful as a dye for use in an optical recording medium for recording and reproduction corresponding to a short wavelength laser.

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.

As an example of a preferable layer structure, 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 can be mentioned. Hereinafter, the optical recording medium of the present invention will be described using a medium having this structure as an example.

The material of the substrate in the optical recording medium of the present invention basically needs to be transparent at the wavelength of recording light and reproducing light.

Examples of such a material include those made of resins such as acrylic resin, methacrylic resin, polycarbonate resin, polyolefin resin (especially amorphous polyolefin), polyester resin, polystyrene resin, epoxy resin, and glass. And a resin in which a resin layer made of a radiation-curable resin such as a photocurable 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.

In the optical recording medium of the present invention, 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.
Such guide grooves and pits are preferably provided at the time of molding the substrate, but may also be provided on the substrate using an ultraviolet curable resin layer. When the guide groove is spiral, the groove pitch is preferably about 0.5 to 1.2 μm.

In order to manufacture the optical recording medium of the present invention, the recording layer containing the azo dye of the present invention is provided on the above-mentioned substrate or, if necessary, an undercoat layer or the like provided on this substrate. Form.

The recording layer is formed by a vacuum deposition method,
Sputtering method, doctor blade method, casting method,
Examples of the method generally used include a thin film forming method such as a spin coating method and an immersion method, and the spin coating method is particularly preferable in terms of mass productivity and cost.

In the case of film formation by spin coating, the number of revolutions is preferably 500 to 5000 rpm. After spin coating, if necessary, treatment such as heating or exposure to solvent vapor may be performed.

The coating solvent for 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 is not particularly limited as long as it is a solvent that 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 Cyclic hydrocarbon solvents such as cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane, n-butylcyclohexane, tert-butylcyclohexane and cyclooctane; tetrafluoropropanol, octafluoropentanol,
Perfluoroalkyl alcohol solvents such as hexafluorobutanol; and hydroxycarboxylic acid ester solvents such as methyl lactate, ethyl lactate and methyl isobutyrate.

The recording layer is formed of a transition metal chelate compound (for example, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α) as a singlet oxygen quencher in order to improve the stability and light resistance of the recording layer. -Diketone, etc.) or a recording sensitivity improver such as a metal compound for improving the recording sensitivity. 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, for example, an ethylenediamine-based complex, an azomethine-based complex, a phenylhydroxyamine-based complex, a phenanthroline-based complex, Dihydroxyazobenzene-based complex,
Dioxime-based complexes, nitrosoaminophenol-based complexes,
Organometallic compounds such as 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 can be used in combination. Other types of dyes are not particularly limited as long as they have appropriate absorption mainly in a recording laser wavelength range. Also, 770-83 like CD-R
Supports recording with laser light in multiple wavelength ranges by using a near infrared laser with a wavelength selected from 0 nm or a dye suitable for recording with a red laser selected from 620 to 690 nm such as DVD-R The optical recording medium can also be used.

Specific examples of the other dyes include metal-containing azo dyes, phthalocyanine dyes, naphthalocyanine dyes, cyanine dyes, azo dyes, squarylium dyes, metal-containing indoaniline dyes, and triarylmethane dyes. Dyes, merocyanine dyes, azurenium dyes,
Examples include naphthoquinone dyes, anthraquinone dyes, indophenol dyes, xanthene dyes, oxazine dyes, and pyrylium dyes.

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 suitable film thickness varies depending on the recording method and the like, but is usually 50 to 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, a material having a sufficiently high reflectance at the wavelength of the reproduction light, for example, Au, Al, Ag, Cu, Ti, Cr, Ni, Pt, Ta,
Cr and Pd metals 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, Mg, Se, H
f, V, Nb, Ru, W, Mn, Re, Fe, Co, Rh, Ir, Cu, Z
Metals and metalloids such as n, Cd, Ga, In, Si, Ge, Te, Pb, Po, Sn, and Bi can be mentioned. Among them, those containing Ag as a main component are particularly preferable because they are inexpensive, easily reflect a high reflectance, 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 the above-mentioned metals, 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 below 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. Examples of the organic material include a thermoplastic resin, a thermosetting resin, an electron beam curable resin, and a UV curable resin. Further, as inorganic substances, SiO ₂ , Si
N ₄ , MgF ₂ , SnO _{2 and the} like can be mentioned.

When the protective layer is formed of a thermoplastic resin, a thermosetting resin, or the like, the protective layer can be formed by applying a coating solution obtained by dissolving these resins in an appropriate solvent 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 of 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. Of these, 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.

A substrate may be further bonded to the reflective layer surface, or two optical recording media may be bonded to each other with the reflective layer surfaces facing each other. 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.

Note that a surface other than the recording / reproducing light incident surface is
A print accepting layer capable of writing (printing) may be provided on various printers such as ink jet and thermal transfer, or various writing utensils.

The laser beam used for the optical recording medium of the present invention is preferably shorter in wavelength for high-density recording, but is more preferably a laser beam of 350 to 530 nm. Representative examples of such laser light include center wavelengths of 410 nm and 515 nm.
Laser light.

An example of a laser beam 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. Is a semiconductor laser capable of continuous oscillation of 740 to 960 nm, or (b) a solid-state laser excited by the semiconductor laser and capable of continuous oscillation having a fundamental oscillation wavelength of 740 to 960 nm. Can also be obtained by wavelength conversion.

As the SHG, any piezo element lacking inversion symmetry may be used.
ADP, BNN, KN, LBO, compound semiconductor, and the like are preferable. As a specific example of the second harmonic, the fundamental oscillation wavelength is
In the case of a 860 nm semiconductor laser, a harmonic of 430 nm is used, and in the case of a semiconductor laser pumped solid laser, a harmonic of 430 nm from a Cr-doped LiSrAlF ₆ crystal (fundamental oscillation wavelength of 860 nm) is used.

The recording on the optical recording medium of the present invention obtained as described above is performed on the recording layer provided on both sides or one side of the substrate.
This is performed by irradiating a laser beam focused to about 0.4 to 0.6 μm. In the portion irradiated with the laser beam, thermal deformation of the recording layer such as decomposition, heat generation, and dissolution occurs due to absorption of the laser beam energy, 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.

[0108]

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.

Example 1 (a) Production Example

[0110]

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3,5-Difluoromethylaniline (0.01 mol) represented by the above structural formula [I] was converted to acetic acid (7.5 m).
1, 2.5 ml of propionic acid and 9 g of phosphoric acid, and the mixture was stirred at 0 to 5 ° C., and 3.52 g of 43% nitrosylsulfuric acid was added dropwise and stirred for 1 hour to perform diazotization. 1.95 g (0.011 mol) of acetoacetanilide represented by the above structural formula [II] was added to 100 ml of deionized water.
The resulting solution was added dropwise to a solution of which the pH was adjusted to 14 with a 25% NaOH aqueous solution. After completion of the dropwise addition, the mixture was further stirred for 3 hours, the reaction solution was filtered, and the filtrate was washed with water. The precipitate was stirred in 100 ml of methanol for 30 minutes to dissolve the impurities in methanol, followed by filtration. The filtrate was dissolved in 200 ml of ethyl acetate, insolubles were removed by filtration, and the filtrate was evaporated by an evaporator to obtain 1.41 g of the following compound [III].
(Yield 33.7%) (mass spectrum m / z = 4)
17 confirmation).

[0112]

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(B) Evaluation Example The compound represented by the above structural formula [III] (maximum absorption wavelength in chloroform λmax = 367.5 nm, molar extinction coefficient is 2.
8 × 10 ⁴ ) was dissolved in octafluoropentanol, and 1.
It was adjusted to 0 wt%. The solution obtained by filtering this solution has a diameter of 12
0 mm, dropped on a 1.2 mm thick injection molded polycarbonate resin substrate, applied by spinner method, and applied
Dry at 30 ° C. for 30 minutes. The maximum absorption wavelength (λ
max) was 357 nm.

Example 2 (a) Production Example

[0115]

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2.43 g (0.01 mol) of p-pentafluoroethylthioaniline represented by the above structural formula [IV]
Was dissolved in 75 ml of demineralized water + 3.125 g of 35% hydrochloric acid with stirring, and cooled to 0 to 5 ° C. Here, an aqueous solution of sodium nitrite 0.76 g / 3 ml was added dropwise so as to keep the temperature at 0 to 5 ° C. for diazotization. This reaction solution was subjected to the above-mentioned structural formula [II]
1.95 g of acetoacetanilide represented by the formula (0.01
1 mol) in 100 ml of demineralized water to give 25%
It was added dropwise to the solution adjusted to pH 14 with an aqueous NaOH solution while adjusting the temperature to 0 to 5 ° C. After completion of the dropwise addition, the mixture was stirred for 3 hours, the reaction solution was filtered, and the filtrate was washed with water. This was dried and 2.44 g of the following compound [V] (yield 56.6)
%).

[0117]

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(B) Evaluation Example The compound represented by the structural formula [V] (maximum absorption wavelength in chloroform: λmax = 370.5 nm, molar extinction coefficient: 2.1
× 10 ⁴ ) was dissolved in octafluoropentanol, and 1.
It was adjusted to 0 wt%. The solution obtained by filtering this solution has a diameter of 12
0 mm, dropped on a 1.2 mm thick injection molded polycarbonate resin substrate, applied by spinner method, and applied
Dry at 30 ° C. for 30 minutes. The maximum absorption wavelength (λ
max) was 347 nm.

Example 3 (a) Production Example

[0120]

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The 3-amino-5- represented by the above structural formula [VI]
2.1 g of (tert-butyl) -isoxazole (0.015 m
ol) was dissolved in 15 ml of acetic acid and 13.5 g of phosphoric acid, stirred at 0 to 5 ° C., and 5.28 g of 43% nitrosylsulfuric acid was added dropwise thereto, followed by stirring for 1 hour for diazotization. A solution obtained by dissolving 3.16 g (0.017 mol) of N-acetoacetyl-p-toluidine represented by the above structural formula [VII] in 150 ml of deionized water and adjusting the pH to 14 with a 25% aqueous NaOH solution. 0-5 ° C, pH 12-1
It was dripped while adjusting to 4. After completion of the dropwise addition, the mixture was further stirred for 3 hours, the reaction solution was filtered, and the filtrate was washed with water. The precipitate was stirred in 150 ml of methanol for 30 minutes to dissolve the impurities in methanol, followed by filtration. The filtrate was dissolved in 200 ml of ethyl acetate, insolubles were removed by filtration, and the filtrate was evaporated with an evaporator. Let it evaporate,
2.11 g (yield 41%) of the following compound [VIII] was obtained.
(Mass spectrum m / z = 342 confirmed).

[0122]

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0.5 g of the compound obtained as described above
Was dissolved in 40 ml of tetrahydrofuran, and a solution of 0.22 g of nickel acetate / 4 ml of methanol was added dropwise at room temperature under stirring. After the dropwise addition, the mixture was stirred for 2 hours and filtered to remove insolubles. Thereafter, 60 ml of demineralized water was added to the filtrate to precipitate a precipitate. After stirring for an additional hour, the product was collected by filtration. The product was washed with water and dried to obtain 0.47 g of a compound represented by the following structural formula [IX] (yield: 86.7).
%).

[0124]

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(B) Evaluation Example The compound represented by the above structural formula [IX] (λmax = 345.5 nm in chloroform, molar extinction coefficient: 3.6 × 10 ⁴⁾
) Was dissolved in octafluoropentanol and adjusted to 1.0 wt%. The solution obtained by filtering this is 120 mm in diameter,
Drop onto a 1.2 mm thick injection molded polycarbonate resin substrate, apply by spinner method, apply
Dry for 0 minutes. Maximum absorption wavelength (λmax) of this coating film
Was 376 nm.

Example 4 (a) Production Example

[0127]

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The above-mentioned 3-amino-5- (tert-butyl) -isoxazole (2.1 g, 0.015 mol) and the acetoacetanilide represented by the above structural formula [X] 2.93 g (0.
017 mol) in the same manner as in Example 3 to obtain 1.15 g (yield 23%) of the following compound [XI].

[0129]

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Compound [XI] obtained as described above
0.5 g was subjected to metallurgy in the same manner, and 0.26 g of the compound represented by the following structural formula [XII] (yield 47.8)
%).

[0131]

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(B) Evaluation Examples Compounds represented by the above structural formula [XII] (λmax in chloroform = 340 nm, molar extinction coefficient 3.8 × 10 ⁴ )
Was dissolved in octafluoropentanol and adjusted to 1.0 wt%. The solution obtained by filtering this is 120 mm in diameter and thickness
Drop onto a 1.2 mm injection molded polycarbonate resin substrate, apply by spinner method, and apply
Dried for minutes. Maximum absorption wavelength (λmax) of this coating film
Was 371 nm.

From the evaluation examples (b) of Examples 1 to 4, a silver film was formed on the coating film thus obtained by, for example, a sputtering method to form a reflection layer, and further, ultraviolet curing. Optical recording media manufactured by applying a mold resin by spin coating or the like and curing it by UV irradiation to form a protective layer can record / reproduce using a semiconductor laser with a center wavelength of 410 nm, for example, based on the value of λmax of the applied film. It can be seen that it is.

[0134]

The azo dye 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. The optical recording medium of the present invention having a recording layer using a dye is useful as an optical recording medium for recording and reproduction corresponding to a short wavelength laser.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Masafumi Adachi 1000-term Kamoshidacho, Aoba-ku, Yokohama-shi, Yokohama-shi F-term in Yokohama Research Laboratory, Mitsubishi Chemical Corporation 2H111 EA03 EA12 EA22 EA25 EA32 EA43 FA01 FB42 HA35 5D029 JA04 JB47 JC03

Claims (9)

[Claims] 1. An azo dye having a structure represented by the following general formula (1). Embedded image (In the formula (1), ring A is an aromatic ring in a broad sense including a heterocyclic ring and a condensed ring, X represents a group having an active hydrogen, Y is O, S or NR ₃ (R ₃ is hydrogen or Alkyl group),
R ₁ and R ₂ are each independently a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, —NR ₄ R ₅ , —OR ₆ or —SR ₇ (however, R ₄ , R ₅ , R ₆ , and R ₇ each represent a hydrogen atom or an arbitrary substituent). ) 2. The azo dye according to claim 1, wherein the azo dye is a monoazo dye represented by the general formula (1). 3. The ring according to claim 2, wherein the ring A is a benzene ring which may have a substituent other than an azo group, or an oxazole ring, a pyrazole ring, an imidazole ring, a thiadiazole ring, an isoxazole ring or a triazole ring. An azo dye characterized by the following. 4. The azo dye according to claim 3, wherein said ring A is a benzene ring. 5. The azo dye according to claim 1, wherein the azo dye is a metal azo chelate dye comprising a compound represented by the following general formula (2) or (3) and a metal. Embedded image (In the formulas (2) and (3), rings A-1 and A-2 represent a heteroaromatic ring formed together with the carbon atom and nitrogen atom to which they are bonded, and X, Y, R ₁ , R ₂ Has the same meaning as in the above general formula (1).) 6. The method according to claim 5, wherein the rings A-1 and A
An azo dye, wherein -2 is an oxazole ring, a pyrazole ring, an imidazole ring, a thiadiazole ring, an isoxazole ring or a triazole ring. 7. The method according to claim 1, wherein at least one of R ₁ and R ₂ is a group containing a cyclic hydrocarbon group which may have a substituent, or a substituent. An azo dye, which is a group containing a heterocyclic ring which may be possessed. 8. An azo dye according to claim 1, wherein the recording layer is provided on a substrate with a recording layer capable of recording or reproducing information with a laser. An optical recording medium comprising: 9. The optical recording medium according to claim 8, wherein a wavelength of a laser used for recording or reproducing information is 350 nm to 530 nm.