JP2000094836A - Optical information recording medium and information recording method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an optical information recording medium displaying high modulation factor. SOLUTION: An optical information recording medium contains a cyanine coloring matter compound represented by the formula. In the formula DYE4 represents monovalent cyanine coloring matter positive ions, (n) represents an integer of 1 or more, R5 and R6 represents independently a substituted group respectively and R7 and R8 represent independently alkyl, alkenyl, aralkyl, aryl or a heterocyclic group, and R5 and R6, R5 and R7, R6 and R8 or R7 and R8 can be connected together each other to form a ring, and (r) and (s) can be same or different each other.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a heat mode optical information recording medium and an information recording method capable of recording and reproducing information using a laser beam. In particular, the present invention is suitable for recording information using near-infrared laser light or visible laser light, for example, a write-once optical disk (CD-R) or a write-once digital video disk (DVD-R). ) Relates to a heat mode type optical information recording medium.

[0002]

2. Description of the Related Art Conventionally, an optical information recording medium (optical disk) on which information can be recorded only once by a laser beam has been known. This optical information recording medium is a write-once CD (so-called C
A typical structure thereof is that a recording layer made of an organic dye, a light reflection layer made of a metal such as gold, and a protective layer made of a resin are laminated in this order on a transparent disk-shaped substrate. Things. Recording of information on the laminate is performed by irradiating near-infrared laser light (usually laser light having a wavelength of about 780 nm) to locally generate heat and deform the recording layer. On the other hand, reading (reproducing) information is usually performed by irradiating a laser beam having the same wavelength as the recording laser beam to reflect a portion where the recording layer is heated and deformed (recorded portion) and a portion where the recording layer is not deformed (unrecorded portion). It does this by detecting differences in rates.

In recent years, with the spread of personal computers and the like, optical information recording media having a higher recording density have been demanded. To increase the recording density, it is effective to reduce the diameter of the laser beam to be irradiated, and it is theoretically known that laser light having a shorter wavelength can be reduced to a smaller diameter, which is advantageous for increasing the density. Have been. Therefore, an optical disk for performing recording and reproduction using a laser beam having a wavelength shorter than 780 nm, which has been conventionally used, is being developed. For example, it is called a write-once digital video disk (so-called DVD-R). Optical disks have been proposed.
This optical disc has a track pitch of 1.6 of CD-R.
A recording layer made of a dye is formed on a transparent disc-shaped substrate having a diameter of 120 mm on which a 0.8 μm pregroove smaller than μm is formed, and a light reflection layer and a protective layer are usually provided on the recording layer. It is manufactured to have a structure in which two disks or a disk-shaped protective substrate having the same shape as the disk are bonded with an adhesive with the recording layer inside. The DVD-R uses visible laser light (normally 630n).
Recording and reproduction are performed by irradiating a laser beam having a wavelength in the range of m to 680 nm.
It is said that recording at a higher density than R is possible.

In designing the DVD-R, since the wavelength of the laser beam used for recording and reproduction is shorter than that of the CD-R, the maximum absorption wavelength of the dye used in the dye recording layer must be shortened accordingly. There is. However, it is generally known that the maximum absorption wavelength of a dye becomes longer as the spread of the pi-electron system, which causes light absorption, becomes longer. Particularly, the cyanine dye which has been practically used in many optical discs in the past is known. In this case, the longer the conjugated methine chain, the longer the wavelength. That is, in order to shorten the absorption maximum wavelength of the dye, it is effective to shorten the length of the conjugated methine chain.However, when the length of the conjugated methine chain is shortened, the extinction coefficient becomes smaller. Inevitably, a decrease in recording sensitivity (a decrease in modulation factor) is likely to occur. Therefore, the conventional CD-R
It is difficult to obtain satisfactory performance as a dye for DVD-R simply by shortening the length of the conjugated methine chain of the dye for use to shorten the absorption maximum wavelength.

On the other hand, in a CD-R, the reflectance at 780 nm must be high enough to be read by a commercially available CD player. In order to increase the amount of light reflected by the metal light reflection layer provided on the dye recording layer, it is preferable that the light absorption by the dye is low, and it is considered that the absorption maximum wavelength of the dye should be shorter. . However, when a dye having an absorption maximum wavelength on the short wavelength side is used, 780 nm
In this case, the change in the reflectance between the recorded portion and the unrecorded portion is reduced, and it becomes difficult to detect the difference. Therefore, in the conventional CD-R, a dye having a high reflectance and a high recording sensitivity is selected and used. For example, as such a dye, a cyanine dye having a benzoindolenine skeleton described in JP-A-64-40382 is preferably used.
However, conventional cyanine dyes are not always satisfactory in both reflectance and recording sensitivity, and further improvement is desired.

Japanese Patent Application Laid-Open No. Hei 4-175188 discloses a method suitable for CD-R, which is said to have a high reflectance and a remarkable improvement in recording and reproducing characteristics such as sensitivity and C / N value. Cyanine dyes have been proposed. And it is described that this cyanine dye can have a monovalent to trivalent anion. However, as a specific example, only a cyanine dye combined with a monovalent anion is disclosed, and there is no description about how to combine a cyanine dye with a divalent or trivalent anion.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide a heat mode optical information recording medium having a high recording sensitivity and a method of recording information when recording information using a laser beam. In particular, an object of the present invention is to provide an optical information recording medium and an information recording method capable of obtaining high recording sensitivity even when using visible laser light (for example, red laser light having a wavelength of 630 to 680 nm). Another object of the present invention is to provide a heat mode optical information recording medium that can achieve high reflectance and high recording sensitivity.

[0008]

According to the research of the present inventors,
By using a cyanine dye compound that combines a polyvalent cation and a cyanine dye component having the same valence, it is possible to manufacture an optical information recording medium having higher recording sensitivity and higher reflectivity than before. Was found.
In particular, a cyanine dye compound obtained by combining a polyvalent anion and a cyanine dye component having a conjugated methine chain with a relatively short length is used for a DVD-ROM that records information using a short-wavelength laser beam.
It has been found that it can be advantageously used in an R-type optical information recording medium.

The present invention is a heat mode optical information recording medium having a recording layer on a substrate on which information can be recorded by irradiating a laser beam, wherein the recording layer has the following general formula (I) An optical information recording medium comprising a cyanine dye compound represented by the formula:

[0010]

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In the formula, DYE ⁺ represents a monovalent cyanine dye cation, n represents an integer of 1 or more, and R ₅ and R ₆
Each independently represents a substituent; R ₇ and R ₈ each independently represent an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group or a heterocyclic group; R ₅ and R ₆ ;
R ₅ and R ₇ , R ₆ and R ₈ or R ₇ and R ₈ may be connected to each other to form a ring, and r and s may be the same or different from each other. The present invention also provides a pre-groove having a track pitch of 0.6 to 0.9 μm, a diameter of 120 ± 0.3 mm and a thickness of 0.6 ± 0.9 μm.
A two-layer laminate in which a recording layer containing a cyanine dye compound represented by the following general formula (I) is provided on the side of the 0.1 mm transparent disc-shaped substrate on which the pregroove is provided, or A pre-groove with a track pitch of 0.6 to 0.9 μm was formed, the diameter was 120 ± 0.3 mm,
Lamination in which a recording layer containing a cyanine dye compound represented by the following general formula (I) is provided on a side of the transparent disc-shaped substrate having a thickness of 0.6 ± 0.1 mm on which the pregroove is provided. Heat-mode light having a thickness of 1.2 ± 0.2 mm, which is obtained by bonding a body and a transparent disk-shaped protective substrate having the same shape as the disk-shaped substrate so that the respective recording layers are on the inside. It is also available on information recording media.

[0012]

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In the formula, DYE ⁺ represents a monovalent cyanine dye cation, n represents an integer of 1 or more, and R ₅ and R ₆
Each independently represents a substituent; R ₇ and R ₈ each independently represent an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group or a heterocyclic group; R ₅ and R ₆ ;
R ₅ and R ₇ , R ₆ and R ₈ or R ₇ and R ₈ may be connected to each other to form a ring, and r and s may be the same or different from each other.

Further, the present invention also provides an information recording method for recording information by irradiating the optical information recording medium having the above structure with a laser beam having a wavelength of 630 nm to 680 nm.

The present invention is preferably in the following modes. (1) The cyanine dye cation in the general formula (I) is a cation represented by the following general formula (II).

[0016]

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In the formula, Za and Zb each independently represent a group of atoms necessary to complete a 5- or 6-membered nitrogen-containing heterocyclic ring, and R ¹ and R ² each independently represent an alkyl group or an aryl group. L ¹ , L ² , L ³ , L ⁴ and L ⁵
Each independently represents a substituted or unsubstituted methine group (however, when there is a substituent on L ^{1 to} L ⁵ , they may be linked to each other to form a ring), and j is 0, 1 or 2 and k
Represents 0 or 1. (2) The cyanine dye cation in the general formula (I) is a cation represented by the following general formula (IIA).

[0018]

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In the formula, Z ¹ and Z ² each independently represent an atom group necessary for completing an indolenine nucleus or a benzoindolenine nucleus, and R ¹ and R ² each independently represent an alkyl group or an aryl group. R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent an alkyl group; L ¹ , L ² , L
³ , L ⁴ and L ⁵ each independently represent a substituted or unsubstituted methine group (however, when there is a substituent on L ^{1 to} L ⁵ , they may be linked to each other to form a ring) , J represents 0, 1 or 2, and k represents 0 or 1. (3) In the above general formula (II) or (IIA), j is
It is 0 or 1. (4) The cyanine dye compound is a compound having an indolenine nucleus having a trimethine chain or a benzoindolenine nucleus.

(5) The substrate has a track pitch of 1.4 to
A pre-groove of 1.8 μm is formed, having a diameter of 120
A transparent disc-shaped substrate having a thickness of ± 0.3 mm and a thickness of 1.2 ± 0.2 mm, wherein a recording layer is provided on the surface on the side where the pre-groove is formed; It is a recording medium. (6) The substrate has a pre-groove with a track pitch of 0.6 to 0.9 μm and a diameter of 120 ± 0.3 mm.
And a transparent disc-shaped substrate having a thickness of 0.6 ± 0.1 mm, and a DVD-R type optical information recording medium in which a recording layer is provided on a surface on a side where the pre-groove is formed. . (7) A light reflecting layer made of metal is further provided on the recording layer. (8) A protective layer is further provided on the light reflecting layer.

[0021]

BEST MODE FOR CARRYING OUT THE INVENTION The optical information recording medium of the present invention is characterized in that the recording layer contains a cyanine dye compound represented by the following general formula (I).

[0022]

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In the formula, DYE ⁺ represents a monovalent cyanine dye cation, n represents an integer of 1 or more, and R ₅ and R ₆
Each independently represents a substituent; R ₇ and R ₈ each independently represent an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group or a heterocyclic group; R ₅ and R ₆ ;
R ₅ and R ₇ , R ₆ and R ₈ or R ₇ and R ₈ may be connected to each other to form a ring, and r and s may be the same or different from each other.

In the cyanine dye compound used in the present invention,
The cyanine dye cation is represented by the following general formula (II)
It is preferably a cation. In the general formula (I)
SO_Three ^-Is preferably R¹, R^Two, Z^aOr Z^bso
At least two of the formed heterocycles are substituted,
Preferably R¹, R ^TwoHas been replaced with General formula (II):

[0025]

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In the general formula (II), Za and Zb each independently represent an atom group necessary for completing a 5- or 6-membered nitrogen-containing heterocyclic ring. R ¹ and R ² each independently represent an alkyl group or an aryl group. L ¹ , L ² ,
L ³ , L ⁴ and L ⁵ each independently represent a substituted or unsubstituted methine group. When L ^{1 to} L ⁵ have a substituent, they may be connected to each other to form a ring. j represents 0, 1 or 2, and k represents 0 or 1.

Examples of the 5- or 6-membered nitrogen-containing heterocyclic ring (nucleus) represented by Za and Zb include, for example, a thiazole nucleus, a benzothiazole nucleus, a naphthothiazole nucleus, a thiazoline nucleus, an oxazole nucleus, a benzooxazole nucleus, and a naphtho. Oxazole nucleus, oxazoline nucleus, selenazole nucleus,
Benzoselenazole nucleus, naphthoselenazole nucleus, selenazoline nucleus, tellurazole nucleus, benzotellurazole nucleus, naphthotellurazole nucleus, tellrazoline nucleus, imidazole nucleus, benzimidazole nucleus, naphthimidazole nucleus, pyridine nucleus, quinoline nucleus, isoquinoline nucleus, imidazo [4,5-b] quinoxaline nucleus, oxadiazole nucleus,
Examples thereof include a thiadiazole nucleus, a tetrazole nucleus, and a pyrimidine nucleus. Among these, benzothiazole nucleus, imidazole nucleus, naphthoimidazole nucleus,
Quinoline nucleus, isoquinoline nucleus, imidazo [4,5-b]
Quinoxaline nucleus, thiadiazole nucleus, tetrazole nucleus,
And pyrimidine nuclei. A benzene ring and a naphthoquinone ring may be further fused to these rings.

The above 5- or 6-membered nitrogen-containing heterocyclic ring may have a substituent. Examples of preferred substituents (atoms) include a halogen atom, a substituted or unsubstituted alkyl group,
An aryl group can be mentioned. As the halogen atom, a chlorine atom is preferable. The alkyl group has 1 carbon atom.
~ 6 linear alkyl groups are preferred. Examples of the substituent of the alkyl group include an alkoxy group (eg, methoxy) and an alkylthio group (eg, methylthio). As the aryl group, phenyl is preferred.

The alkyl group represented by R ¹ and R ² may have a substituent, and preferably has 1 carbon atom.
To 18 (more preferably 1 to 8, especially 1 to 6) linear, cyclic or branched alkyl groups. The aryl group represented by R ¹ and R ² may have a substituent, and is preferably an aryl group which may have a substituent having 6 to 18 carbon atoms.

Preferred examples of the substituents on the alkyl group or the aryl group represented by R ¹ and R ² include the following. A substituted or unsubstituted aryl group having 6 to 18 carbon atoms (for example, phenyl, chlorophenyl, anisyl, toluyl, 2,4-di-t-amyl, 1-naphthyl), an alkenyl group (for example, vinyl, 2-methyl Vinyl), an alkynyl group (eg, ethynyl, 2-methylethynyl, 2-phenylethynyl),
A halogen atom (eg, F, Cl, Br, I), a cyano group, a hydroxyl group, a carboxyl group, an acyl group (eg, acetyl, benzoyl, salicyloyl, pivaloyl), an alkoxy group (eg, methoxy, butoxy, cyclohexyloxy), Aryloxy group (for example, phenoxy, 1-naphthoxy), alkylthio group (for example, methylthio, butylthio, benzylthio, 3-methoxypropylthio), arylthio group (for example, phenylthio, 4-chlorophenylthio), alkylsulfonyl group (for example, Methanesulfonyl, butanesulfonyl), arylsulfonyl group (for example, benzenesulfonyl, paratoluenesulfonyl), and having 1 to 10 carbon atoms
A carbamoyl group, an amide group having 1 to 10 carbon atoms, an acyloxy group having 2 to 10 carbon atoms, and 2-1 carbon atom
A heteroaromatic ring such as pyridyl, thienyl, furyl, thiazolyl, imidazolyl, pyrazolyl, a pyrrolidine ring, a piperidine ring, a morpholine ring, a pyran ring, a thiopyran ring;
An aliphatic heterocycle such as a dioxane ring and a dithiolane ring).

In the present invention, R ¹ and R ² are
Each is an unsubstituted linear alkyl group having 1 to 8 carbon atoms (preferably having 1 to 6 carbon atoms, particularly 1 to 4 carbon atoms), or an alkoxy group (particularly, methoxy) or an alkylthio group (particularly, , Methylthio) is preferably a linear alkyl group having 1 to 8 carbon atoms (preferably having 1 to 6 carbon atoms, particularly 1 to 4 carbon atoms).

The methine groups represented by L ^{1 to} L ⁵ may have a substituent. Preferred examples of the substituent include those exemplified as the preferred substituents of the alkyl group having 1 to 18 carbon atoms, the aralkyl group, and the alkyl group or the aryl group represented by R ¹ and R ^2. be able to. Of these, alkyl groups (eg,
Preferred are methyl), an aryl group (eg, phenyl), a halogen atom (eg, Cl, Br), and an aralkyl group (eg, benzyl). In the present invention, j and k are preferably each independently 0 or 1.

The substituents on L ^{1 to} L ⁵ may be linked to each other to form a ring. The preferred number of ring members is a 5- or 6-membered ring, and two or more of these rings may be condensed. The linking position depends on the number of methine chains formed. For example, when the methine chain formed by L ^{1 to} L ⁵ is a pentamethine chain, the preferred linking positions are L ¹ and L ³ , L ² and L ⁴ , and L ³ and L ⁵ . The connecting position in the case of forming a double condensed ring is L ¹ and L ³ and L ^5. In this case, L ¹ and R ¹ , L ⁵ and R ² , and L ³
And R ² may be linked to each other to form a ring, and the number of ring members is preferably a 5- or 6-membered ring. In the present invention, the ring formed by the substituents on L ^{1 to} L ⁵ is preferably a cyclohexene ring.

The cyanine dye cation in the cyanine dye compound used in the present invention is preferably a cation represented by the following formula (IIA). General formula (IIA):

[0035]

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In the general formula (IIA), Z ¹ and Z ² represent an atomic group necessary for completing an indolenine nucleus or a benzoindolenine nucleus. R ¹ and R ² each independently represent an alkyl group or an aryl group. R ³ , R ⁴ ,
R ⁵ and R ⁶ each independently represent an alkyl group. L ¹ ,
L ² , L ³ , L ⁴ and L ⁵ each independently represent a substituted or unsubstituted methine group. When L ^{1 to} L ⁵ have a substituent, they may be connected to each other to form a ring. j represents 0, 1 or 2, and k represents 0 or 1.

The indolenine nucleus or benzoindolenine nucleus represented by Z ¹ and Z ² may have a substituent. Examples of the substituent (atom) include a halogen atom and an aryl group. As the halogen atom, a chlorine atom is preferable. As the aryl group,
Phenyl is preferred.

The alkyl groups represented by R ³ , R ⁴ , R ⁵ and R ⁶ are preferably linear, branched or cyclic alkyl groups having 1 to 18 carbon atoms. Also R
³ and R ⁴ , and R ⁵ and R ⁶ may be respectively linked to form a ring. The alkyl group represented by R ³ , R ⁴ , R ⁵ and R ⁶ may have a substituent. Preferred examples of the substituent include those described as examples of preferred substituents of the alkyl group or the aryl group represented by R ¹ and R ² . In the present invention, the alkyl groups represented by R ³ , R ⁴ , R ⁵ and R ⁶ are each a straight-chain unsubstituted alkyl group having 1 to 6 carbon atoms (particularly, methyl, ethyl ) Is preferable.

In the general formula (IIA), R ¹ and R ² ,
L ¹ , L ² , L ³ , L ⁴ and L ⁵ , j and k, and X
^n- and n each have the same meaning as those described in the general formula (II). Preferred examples thereof are also the same as those described in the general formula (II).

Preferred specific examples of the portion represented by [DYE ⁺ ]-(SO ^3- ) _n in the compound represented by the general formula (I) according to the present invention are shown below.

[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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In the general formula (I), the following general formula (I-
The part represented by 2) will be described in detail.

[0050]

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In the formula, R ₅ and R ₆ each independently represent a substituent, and R ₇ and R ₈ each independently represent an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group or a heterocyclic group. R ₅ and R ₆ , R ₅ and R ₇ , R ₆ and R _8, or R ₇ and R ₈ may be linked to each other to form a ring, and r and s each independently represent 0 to 4 Represents the integer of
When r and s are two or more, a plurality of r and s may be the same or different from each other.

The alkyl group represented by R ₇ and R ₈ is preferably a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms. is there. These may be linear, branched, or cyclic. Examples of these include methyl, ethyl, n-propyl, isopropyl, n
-Butyl, isobutyl, t-butyl, n-hexyl, neopentyl, cyclohexyl, adamantyl, cyclopropyl and the like.

Examples of the substituent of the alkyl group include the following. A substituted or unsubstituted alkenyl group having 2 to 18 carbon atoms (preferably 2 to 8 carbon atoms) (eg vinyl); 2 to 18 carbon atoms (preferably 2 carbon atoms)
To 8) substituted or unsubstituted alkynyl groups (eg, ethynyl); substituted or unsubstituted aryl groups having 6 to 10 carbon atoms (eg, phenyl, naphthyl); halogen atoms (eg,
F, Cl, Br and the like); a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms (preferably 1 to 8 carbon atoms) (eg,
Methoxy, ethoxy); a substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms (eg, phenoxy, p-methoxyphenoxy); substituted or unsubstituted having 1 to 18 carbon atoms (preferably 1 to 8 carbon atoms). Alkylthio group (eg,
Methylthio, ethylthio); a substituted or unsubstituted arylthio group having 6 to 10 carbon atoms (eg, phenylthio);
A substituted or unsubstituted acyl group having 2 to 18 carbon atoms (preferably 2 to 8 carbon atoms) (eg, acetyl, propionyl);

C1-18 (preferably C1-18)
8) a substituted or unsubstituted alkylsulfonyl group or arylsulfonyl group (eg, methanesulfonyl, p-
A substituted or unsubstituted acyloxy group having 2 to 18 carbon atoms (preferably 2 to 8 carbon atoms) (eg, acetoxy, propionyloxy);
18 (preferably 2 to 8 carbon atoms) substituted or unsubstituted alkoxycarbonyl group (eg, methoxycarbonyl,
Ethoxycarbonyl); a substituted or unsubstituted aryloxycarbonyl group having 7 to 11 carbon atoms (eg, naphthoxycarbonyl); an unsubstituted amino group, or 1 to 1 carbon atom
18 (preferably 1 to 8 carbon atoms) substituted amino group (eg,
Methylamino, dimethylamino, diethylamino, anilino, methoxyphenylamino, chlorophenylamino, pyridylamino, methoxycarbonylamino, n-
Butoxycarbonylamino, phenoxycarbonylamino, methylcarbamoylamino, ethylthiocarbamoylamino, phenylcarbamoylamino, acetylamino, ethylcarbonylamino, ethylthiocarbamoylamino, cyclohexylcarbonylamino, benzoylamino, chloroacetylamino, methylsulfonylamino);

C1-18 (preferably C1-18)
8) substituted or unsubstituted carbamoyl group (eg, unsubstituted carbamoyl, methylcarbamoyl, ethylcarbamoyl, n-butylcarbamoyl, t-butylcarbamoyl, dimethylcarbamoyl, morpholinocarbamoyl, pyrrolidinocarbamoyl); unsubstituted sulfamoyl group Or 1 to 18 carbon atoms (preferably 1 to 18 carbon atoms)
8) a substituted sulfamoyl group (eg, methylsulfamoyl, phenylsulfamoyl); a cyano group; a nitro group;
Carboxy group; hydroxyl group; heterocyclic group (eg, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, imidazole ring, benzimidazole ring, indolenine ring, pyridine ring, piperidine ring, pyrrolidine ring, morpholine ring, sulfolane ring , Furan ring, thiophene ring, pyrazole ring, pyrrole ring, chroman ring, coumarin ring).

The alkenyl group represented by R ₇ and R ₈ is preferably a substituted or unsubstituted alkenyl group having 2 to 18 carbon atoms, more preferably a substituted or unsubstituted alkenyl group having 2 to 8 carbon atoms. Yes, for example, vinyl,
Allyl, 1-propenyl, 1,3-butadienyl and the like can be mentioned. As the substituent for the alkenyl group, those mentioned above as the substituent for the alkyl group are preferable.

The alkynyl group represented by R ₇ and R ₈ is preferably a substituted or unsubstituted alkynyl group having 2 to 18 carbon atoms, more preferably a substituted or unsubstituted alkynyl group having 2 to 8 carbon atoms. Yes, for example, ethynyl, 2-propynyl and the like. As the substituent for the alkynyl group, those described above as the substituent for the alkyl group are preferable.

The aralkyl group represented by R ₇ and R ₈ is preferably a substituted or unsubstituted aralkyl group having 7 to 18 carbon atoms, for example, benzyl, methylbenzyl and the like.

The aryl group represented by R ₇ and R ₈ is preferably a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, such as phenyl and naphthyl. As the substituent of the aryl group, those described above as the substituent of the alkyl group are preferable. In addition to these, an alkyl group (eg, methyl, ethyl, etc.) is also preferable.

The heterocyclic group represented by R ₇ and R ₈ is
It is a 5- or 6-membered saturated or unsaturated heterocyclic ring composed of a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and examples thereof include an oxazole ring, a benzoxazole ring, a thiazole ring, and a benzothiazole. Ring, imidazole ring, benzimidazole ring, indolenine ring,
Examples include a pyridine ring, a piperidine ring, a pyrrolidine ring, a morpholine ring, a sulfolane ring, a furan ring, a thiophene ring, a pyrazole ring, a pyrrole ring, a chroman ring, and a coumarin ring. The heterocyclic group may be substituted, and in this case, the substituent is preferably those exemplified as the substituent for the alkyl group.

The substituents represented by R ₅ and R ₆ have the same meanings as those described above for the alkyl group. In addition to these, alkyl groups (eg, methyl, ethyl, etc.)
Can also be mentioned. In the present invention, R ₅ and R
_The substituent represented by ₆ is preferably a hydrogen atom or an alkyl group. Particularly preferred is a hydrogen atom.
Hydrogen atom 3

The partial structure represented by the general formula (I-2) is
It is particularly preferably represented by the following general formula (I-3) or (I-4).

[0063]

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Where R₁₇And R₁₈Are respectively described above
R_FiveAnd R₆Has the same meaning as the substituent represented by
The preferred ranges are the same for each. R₁₉Passing
And R ₂₀Is the above-mentioned R₇And R₈The position represented by
Synonymous with a substitution group, and for each, its preferred
Are the same. r and s are each independently 0 to 4
Represents an integer, and when r and s are 2 or more,
r and s may be the same or different from each other
No.

[0065]

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In the formula, R ₂₁ and R ₂₂ have the same meanings as the substituents represented by R ₅ and R ₆ , respectively, and their preferred ranges are also the same. It is also preferred that R ₂₁ and R ₂₂ are connected to each other to form a carbocyclic or heterocyclic ring, and particularly preferable is a condensed aromatic ring with a pyridine ring to which R ₂₁ and R ₂₂ are respectively bonded. . r and s each independently represent an integer of 0 to 4,
When r and s are two or more, a plurality of r and s may be the same or different from each other.

Examples of the portion represented by the general formula (I-2) (represented by "B-") in the dye compound represented by the general formula (I) used in the present invention are specifically described below. I do.

[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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Preferred specific examples of the compounds used in the present invention are shown in Table 1 below.

[0079]

[Table 1]

[0080]

[Table 2]

In Table 1, the compound examples are [DYE ⁺ ]
- (SO ^3-) Anion general formula represented by _{n + 1} (I-
It is a combination with the cation moiety represented by 2). For example, an example of compound No. 1 will be described below. Examples of compounds represented by compound No. 1 [anion part (A-1) / cation part (B-5)] are represented by the following formulas.

[0082]

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The same applies to compounds No. 2 and subsequent compounds. The compounds represented by the above general formula (I) according to the present invention may be used alone or in combination of two or more. The compound represented by the general formula (I) according to the present invention can be easily synthesized with reference to the description of the following known literatures.

These documents include, for example, F.
M. Hammer, The Cyanine Soybeans and Rerated Compounds 5 (Interscience Publishers, NY, 1964), p.・ Dietz, Aria Tadzière (Nikolai Tyutyulkov, Jurgen Fabian, Achim U
Lehlhorn, Fritz Dietz, Alia Tadjer) “Polymethine soybean”, St. Kliment Ohridski University Press, Sofia (St. Kliment Ohridski Uni)
versity Press, Sophia), pp. 23-38; DMSturmer, "Heterocyclic, Compounds-Special Topics in Heterocyclic Chemistry".
Compounds-Special topics in heterocyclic chemistr
y), Chapter 18, Section 14, pp. 482-515, John Wiley & Sons
) Sha, New York, London, (1977);
"Rodd's Chemistry of Carbon Compounds", (2n
d.Ed.vol.IV, part B, 1977), Chapter 15, Chapter 3
69-422, (2nd. Ed. Vol. IV, part B, 1985), Chapter 15, pp. 267-296, Elsbyer Science Public Company, Inc.
ier Science Public Company Inc.), New York, and the like.

More specifically, [DYE ⁺ ]-(SO ₃
^- ) _{n + 1} (M ⁺ ) _n , wherein M represents a cation such as sodium ion, potassium ion, ammonium ion, pyridinium ion, triethylammonium ion, N-ethylpyridinium ion, and The cation represented by the general formula (I-2) is Cl ⁻ , B
r ^-, I ^-, anions and combined in a suitable solvent and a salt formed by such p-toluenesulfonate, for example, methanol, water, or after mixing in a mixture thereof, be precipitated as crystals Can be obtained by As an example, compound 41 is obtained by mixing a methanol solution of an N-ethylpyridinium salt of A-28 with a methanol solution of a bromide of B-54, collecting crystals precipitated by filtration, washing with methanol, and drying. Yields a brown powder with a melting point of 213-217 degrees.

The optical information recording medium of the present invention has a recording layer containing a cyanine dye compound represented by the aforementioned general formula (I) on a substrate. The cyanine dye compound according to the present invention can be advantageously used in a CD-R or DVD-R as an optical information recording medium. In particular, in a DVD-R type optical information recording medium, a dye compound having an indolenine nucleus having a trimethine chain or a benzoindolenine nucleus in the cyanine dye compound represented by the general formula (IIA) is advantageously used. Can be

The optical information recording medium of the present invention preferably has the following configuration. The CD-R type optical information recording medium has a diameter of 120 ± 0.3 mm and a thickness of 1.2 ± with a pre-groove having a track pitch of 1.4 to 1.8 μm.
It is preferable that a recording layer, a light reflection layer, and a protective layer are provided in this order on a 0.2 mm transparent disk-shaped substrate. The DVD-R type optical information recording medium preferably has the following two aspects. Track pitch 0.6
120 ± 1 mm with pre-groove of ~ 0.9 μm
Two laminates comprising a recording layer and a light reflecting layer provided on a transparent disk-shaped substrate having a thickness of 0.3 mm and a thickness of 0.6 ± 0.1 mm are joined so that each recording layer is on the inside. And
Thickness 1.2 ± 0.2 mm. Alternatively, a pre-groove having a track pitch of 0.6 to 0.9 μm is formed with a diameter of 120 ± 0.3 mm and a thickness of 0.6 ±
A laminate in which a recording layer and a light reflection layer are provided on a 0.1 mm transparent disc-shaped substrate, and a transparent disc-shaped protective substrate having the same shape as the disc-shaped substrate of the laminate, wherein the recording layer is inside. And a thickness of 1.2 ± 0.2 mm. The DVD-R type optical information recording medium may have a configuration in which a protective layer is further provided on the light reflecting layer.

Hereinafter, a method for manufacturing an optical information recording medium will be described. The DVD-R type optical information recording medium is basically a CD-R optical recording medium except that a substrate on which a pre-group having a narrower track pitch is formed than a CD-R is used in order to achieve a higher recording density. It can be manufactured using a material used for manufacturing an optical information recording medium of -R. That is, the optical information recording medium of the DVD-R is
A recording layer, and a light reflection layer, and if desired, a laminate in which a protective layer is formed in order, two sheets are formed, and these two sheets are joined with an adhesive, or alternatively, the laminate and the laminate, It can be manufactured by bonding a substrate and a disk-shaped protective substrate having the same shape with an adhesive in the same manner. Therefore, in manufacturing the DVD-R optical information recording medium, the steps other than the final step of bonding the substrates are performed in the same manner as the CD-R optical information recording medium.

The optical information recording medium of the present invention can be manufactured, for example, by the following method. The substrate of the optical information recording medium can be arbitrarily selected from various materials used as the substrate of the conventional optical information recording medium. As the substrate material, for example, glass; polycarbonate; acrylic resin such as polymethyl methacrylate;
Examples thereof include polyvinyl chloride resins such as polyvinyl chloride and vinyl chloride copolymer; epoxy resins; amorphous polyolefins and polyesters, and these may be used in combination if desired. Note that these materials can be used in the form of a film or a rigid substrate. Among the above materials, polycarbonate is preferred from the viewpoints of moisture resistance, dimensional stability, cost, and the like.

An undercoat layer may be provided on the surface of the substrate on which the recording layer is provided, for the purpose of improving flatness, improving adhesion, and preventing the recording layer. Examples of the material of the undercoat layer include polymethyl methacrylate, acrylic acid / methacrylic acid copolymer, styrene / maleic anhydride copolymer, polyvinyl alcohol, N-methylolacrylamide, styrene / vinyltoluene copolymer, and chlorosulfonation. High molecular substances such as polyethylene, nitrocellulose, polyvinyl chloride, chlorinated polyolefin, polyester, polyimide, vinyl acetate / vinyl chloride copolymer, ethylene / vinyl acetate copolymer, polyethylene, polypropylene and polycarbonate; and silane coupling agents And the like. The undercoat layer is formed by dissolving or dispersing the above substances in an appropriate solvent to prepare a coating solution, and then applying the coating solution to the substrate surface by a coating method such as spin coating, dip coating, or extrusion coating. can do.
The thickness of the undercoat layer is generally in the range of 0.005 to 20 μm, preferably in the range of 0.01 to 10 μm.

On the substrate (or the undercoat layer), usually, grooves for tracking or irregularities (pre-grooves) representing information such as address signals are formed. This pregroove is preferably formed directly on the substrate when injection molding or extrusion molding of a resin material such as polycarbonate. The pitch (track pitch) of the pre-groove differs depending on the CD-R type or DVD-R type. Normal CD
In the -R type, it is preferable to be formed with a track pitch having a width of 1.4 to 1.8 μm. Further, in the DVD-R type, it is preferable that the track is formed with a track pitch of 0.6 to 0.9 μm.

The depth of the pregroove is 300 to 2000 mm.
Is preferable, and the half-value width is in the range of 0.1.
It is preferably in the range of 2 to 0.9 μm. Further, by setting the depth of the pre-groove in the range of 1500 to 2000 °, the sensitivity can be improved without substantially lowering the reflectance, which is particularly advantageous for manufacturing a CD-R type optical information recording medium.

A dye recording layer is provided on a substrate. The dye recording layer contains the cyanine dye compound represented by the general formula (I) described above. Dyes other than the cyanine dye compound represented by formula (I) and other compounds may be used in combination. Preferred as the dye used in combination in the recording layer is a dicarbocyanine dye having a benzoindolenine nucleus, which is particularly preferable when used as a CD-R. The recording layer preferably contains various compounds known as a singlet oxygen quencher in order to further improve the light resistance of the recording layer. As the singlet oxygen quencher, those described in publications such as publicly known patent specifications can be used. Specific examples thereof are described in JP-A-58-175693 and JP-A-59-8.
Nos. 1194, 60-18387, 60-1958
No. 6, No. 60-19587, No. 60-35054,
No. 60-36190, No. 60-36191, No. 60
-44554, 60-45555, 60-44
No. 389, No. 60-44390, No. 60-54892
No. 60-47069, No. 63-209995,
JP-A-4-25492, JP-B-1-38680, JP-A-6-26028, etc., German Patent 3503
No. 99 and the Journal of the Chemical Society of Japan, October 1992, p. 1141, and the like.

The recording layer is formed by dissolving the above-mentioned dye and, if desired, a quencher and a binder in a solvent to prepare a coating solution, and then applying the coating solution to the substrate surface to form a coating film. It can be performed by drying. Examples of the solvent for the dye layer coating solution include esters such as butyl acetate and cellosolve acetate; methyl ethyl ketone;
Ketones such as cyclohexanone and methyl isobutyl ketone; chlorinated hydrocarbons such as dichloromethane, 1,2-dichloroethane and chloroform; amides such as dimethylformamide; hydrocarbons such as cyclohexane; ethers such as tetrahydrofuran, ethyl ether and dioxane; Alcohols such as propanol, isopropanol and n-butanol diacetone alcohol; fluorinated solvents such as 2,2,3,3-tetrafluoropropanol; glycols such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and propylene glycol monomethyl ether Ethers and the like can be mentioned. The above solvents can be used alone or in combination of two or more kinds in consideration of the solubility of the dye to be used. Various additives such as an antioxidant, a UV absorber, a plasticizer, and a lubricant may be further added to the coating solution according to the purpose.

When a binder is used, examples of the binder include natural organic high-molecular substances such as gelatin, cellulose derivatives, dextran, rosin and rubber; and hydrocarbon-based substances such as polyethylene, polypropylene, polystyrene and polyisobutylene. Resin, polyvinyl chloride, polyvinylidene chloride, vinyl resin such as polyvinyl chloride / polyvinyl acetate copolymer, acrylic resin such as polymethyl acrylate, polymethyl methacrylate, polyvinyl alcohol, chlorinated polyethylene, epoxy resin, Synthetic organic polymers such as butyral resins, rubber derivatives, and initial condensates of thermosetting resins such as phenol / formaldehyde resins can be given. When a binder is used in combination as a material for the recording layer, the amount of the binder used is generally 0.1 to 0.1 with respect to the dye.
It is in the range of 01 times to 50 times (weight ratio), preferably in the range of 0.1 times to 5 times (weight ratio). The concentration of the coating solution thus prepared is generally from 0.01 to
In the range of 10% by weight, preferably 0.1-5% by weight
In the range.

Examples of the coating method include a spray method, a spin coating method, a dip method, a roll coating method, a blade coating method, a doctor roll method, and a screen printing method. The recording layer may be a single layer or a multilayer. The thickness of the recording layer is generally in the range from 20 to 500 nm, preferably in the range from 50 to 300 nm.

On the recording layer, a light reflection layer is provided for the purpose of improving the reflectance at the time of reproducing information. The light-reflective substance, which is the material of the light-reflective layer, is a substance having a high reflectance with respect to laser light.
i, Zr, Hf, V, Nb, Ta, Cr, Mo, W, M
n, Re, Fe, Co, Ni, Ru, Rh, Pd, I
r, Pt, Cu, Ag, Au, Zn, Cd, Al, G
a, In, Si, Ge, Te, Pb, Po, Sn, Bi
Metal and semimetal or stainless steel. Of these, preferred are Cr, N
i, Pt, Cu, Ag, Au, Al and stainless steel. These substances may be used alone, or may be used in combination of two or more kinds or as an alloy. The light reflecting layer can be formed on the recording layer by, for example, vapor deposition, sputtering or ion plating of the above light reflecting substance. The thickness of the light reflecting layer is generally in the range of 10 to 300 nm,
A range of 200 nm is preferred.

A recording layer and the like are physically and
A protective layer is provided for the purpose of chemical protection. What
In the case of manufacturing a DVD-R type optical information recording medium,
It is not always necessary to provide a protective layer. Used for protective layer
Examples of the material to be used are SiO, SiO_Two , MgF_Two ,
SnO _Two , Si_Three N_Four Such as inorganic substances, thermoplastic resin, heat
List organic substances such as curable resin and UV curable resin
Can be. The protective layer is formed, for example, by extrusion of plastic.
Laminate the resulting film on the reflective layer via an adhesive.
Can be formed. Or vacuum
Provided by methods such as vapor deposition, sputtering, coating, etc.
Is also good. In the case of thermoplastic resin and thermosetting resin,
Prepared a coating solution by dissolving them in an appropriate solvent.
It is also formed by applying this coating solution and drying
can do. In the case of UV curable resin,
Alternatively, after dissolving in an appropriate solvent to prepare a coating solution,
Applying this coating liquid and irradiating it with UV light to cure it
Can also be formed. In these coating solutions
Also includes various antistatic agents, antioxidants, UV absorbers, etc.
Additives may be added according to the purpose. The thickness of the protective layer is
Generally, it is in the range of 0.1 to 100 μm. The above process
The recording layer, light reflection layer and protective layer on the substrate.
A laminated body can be manufactured.

The CD-R type optical information recording medium can be manufactured by the above steps. In addition, the DVD-R type optical information recording medium faces the two laminated bodies manufactured as described above such that the recording layers are on the inside,
It can be manufactured by joining using an adhesive. Alternatively, the laminated body manufactured as described above and a disk-shaped protective substrate having the same shape as the substrate of the laminated body are similarly faced to each other such that the recording layer is on the inside, and are bonded using an adhesive. Can be manufactured.

The optical information recording method of the present invention is carried out, for example, as follows, using the above optical information recording medium. First,
While rotating the optical information recording medium at a constant linear velocity (1.2 to 14 m / sec in the case of the CD format) or a constant angular velocity, recording light such as a semiconductor laser beam is irradiated from the substrate side. By this light irradiation, a cavity is formed at the interface between the recording layer and the reflective layer (the cavity is formed by deforming the recording layer or the reflective layer, or by deforming both layers),
It is considered that information is recorded when the substrate is overlaid and deformed, or when the refractive index changes due to discoloration of the recording layer or a change in the association state. The recording light is generally 500 n
A semiconductor laser beam having an oscillation wavelength in the range of m to 850 nm is used. In the present invention, a semiconductor laser beam having an oscillation wavelength in the range of 770 to 790 nm is used as a material suitable for CD-R.
A semiconductor laser beam having an oscillation wavelength in the range of 630 to 680 nm is used as a material suitable for DR. Preferred is a red laser beam having an oscillation wavelength in the range of 635-645 nm. Reproduction of the information recorded as described above can be performed by irradiating the semiconductor laser light from the substrate side while rotating the optical information recording medium at the same constant linear speed as above, and detecting the reflected light. it can.

[0101]

EXAMPLES Examples of the present invention will be described below. However, these examples do not limit the present invention. Example 1 The cyanine dye compound 41 was changed to 2,2
It was dissolved in 3,3-tetrafluoropropanol to obtain a coating liquid for forming a recording layer. A polycarbonate substrate having a spiral pre-groove (track pitch: 0.8 μm, groove width: 0.4 μm, groove depth: 0.15 μm) formed on the surface thereof by injection molding (diameter:
The recording layer (thickness (within the groove): about 200 nm) was formed on the surface of the pre-groove side (120 mm, thickness: 0.6 mm) by spin coating.

Au was sputtered on the recording layer to form a light reflecting layer having a thickness of about 100 nm, and a laminated body having the recording layer and the light reflecting layer provided on the substrate in this order was prepared. Separately, a transparent polycarbonate substrate (disk-shaped protective substrate)
(Diameter: 120 mm, thickness: 0.6 mm) was prepared.
Then, the laminate obtained above and the disc-shaped protective substrate were bonded together (thickness: 1.2 mm) using an adhesive (manufactured by Three Bond) so that the recording layer was on the inside. Through the above steps, a DVD-R type optical information recording medium according to the present invention was obtained.

Example 2 The procedure of Example 1 was repeated, except that the same amount of the cyanine dye compound 6 was used instead of the cyanine dye compound 41. An optical information recording medium was obtained.

Comparative Example 1 In Example 1, a cyanine dye compound (compound C-C) was prepared by combining the following monovalent anion and the following monovalent cation component of cyanine dye in place of the cyanine dye compound 41: A DVD-R type optical information recording medium for comparison was obtained in the same manner as in Example 1 except that the same amount of 1) was used.

[0105]

Embedded image

Comparative Example 2 In Example 1, a cyanine dye compound (compound C-C) in which the following monovalent anion and a cyanine dye monovalent cation component were combined in place of the cyanine dye compound 41 described below. An optical information recording medium for comparison (DVD-R) was obtained in the same manner as in Example 1 except that the same amount of 2) was used.

[0107]

Embedded image

[Evaluation as Optical Information Recording Medium] Semiconductor laser light having a wavelength of 635 nm was condensed on the obtained optical information recording medium with a lens having an NA of 0.6, and a linear velocity of 3.68 m / s was obtained.
Recording a signal at the modulation frequency 4 mH _Z, were measured C / N. Furthermore, after irradiating the optical information recording medium with a Xe lamp (140,000 Lux) for 8 hours, the C / N was measured in the same manner. Table 2 shows the obtained evaluation results.

Table 2 ────────────────────────────── Dye C / N (dB) at recording power of 8 mW Before light irradiation After light irradiation {Example 1 41 50 48 Example 2 6 48 47} {Comparative Example 1 C-1 49 32 Comparative Example 2 C-2 48 33} ────────────────────────

From the results shown in Table 2 above, it was found that D having a recording layer containing the cyanine dye compound of the present invention in which a divalent anion and two cyanine dye monovalent cations were combined was used.
VD-R (Examples 1-2) is a DVD-R having a recording layer containing a conventional cyanine dye compound (Comparative Example 1,
It turns out that it has high light resistance compared with 2).

[0111]

According to the present invention, an optical information recording medium having a high C / N can be obtained by using a cyanine dye compound obtained by combining a cyanine dye cation component. In particular, even when laser light in the visible region is used, C / N
Therefore, it can be said that the cyanine dye compound is advantageous for DVD-R. Even when the specific cyanine dye compound according to the present invention is applied to a CD-R, it can be advantageously used for improving light fastness.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 2H111 EA03 EA12 EA22 EA25 EA32 EA33 EA37 EA39 EA43 FA01 FA12 FA14 FA23 FA33 FA35 FA37 FB43 4H056 CA01 CC02 CC08 CE03 CE06 DD03 DD06 DD19 DD23 FA06 5D029 JA04 KB03 KB11 RA03 RA03 5D090 AA01 BB03 CC01 CC14 DD01 EE01 GG07 KK06

Claims (8)

[Claims] 1. A heat mode optical information recording medium having a recording layer on a substrate on which information can be recorded by irradiating a laser beam, wherein the recording layer is represented by the following general formula (I). Optical information recording medium characterized by containing a cyanine dye compound to be used: In the formula, DYE ⁺ represents a monovalent cyanine dye cation, n represents an integer of 1 or more, R ₅ and R ₆ each independently represent a substituent, and R ₇ and R ₈ each independently represent Represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group or a heterocyclic group, wherein R ₅ and R ₆ , R ₅ and R ₇ , R ₆ and R ₈ or R ₇ and R ₈ are each connected to each other; To form a ring, and r and s may be the same or different from each other. 2. The optical information recording medium according to claim 1, wherein the cyanine dye cation is a cation represented by the following general formula (II): Wherein, Za and Zb each represents an atomic group necessary to complete a nitrogen-containing heterocyclic ring each independently a 5- or 6-membered, R ¹
And R ² each independently represent an alkyl group or an aryl group, and L ¹ , L ² , L ³ , L ⁴ and L ⁵ each independently represent a substituted or unsubstituted methine group (provided that L ¹ to L
^When there is a substituent on ⁵ ), they may be connected to each other to form a ring), j represents 0, 1 or 2, and k represents 0 or 1. 3. The optical information recording medium according to claim 1, wherein the cyanine dye cation is a cation represented by the following general formula (IIA): In the formula, Z ¹ and Z ² each independently represent an atom group necessary for completing an indolenine nucleus or a benzoindolenine nucleus, and R ¹ and R ² each independently represent an alkyl group or an aryl group. , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent an alkyl group, and L ¹ , L ² , L ³ , L ⁴ and L ⁵ each independently represent a substituted or unsubstituted methine group. (However, when there is a substituent on L ^{1 to} L ⁵ , they may be connected to each other to form a ring), j represents 0, 1 or 2, and k represents 0 or 1. 4. A substrate having a track pitch of 1.4 to 1.8.
A pre-groove of μm was formed, and the diameter was 120 ± 0.2.
2. The optical information recording medium according to claim 1, wherein the optical information recording medium is a transparent disc-shaped substrate having a thickness of 3 mm and a thickness of 1.2 ± 0.2 mm, and a recording layer is provided on a surface on which the pregroove is formed. . 5. A substrate having a track pitch of 0.6 to 0.9.
A pre-groove of μm was formed, and the diameter was 120 ± 0.2.
2. The optical information recording medium according to claim 1, wherein the optical information recording medium is a transparent disk-shaped substrate having a thickness of 3 mm and a thickness of 0.6 ± 0.1 mm, and a recording layer is provided on a surface on a side where the pre-groove is formed. . 6. A pregroove having a track pitch of 0.6 to 0.9 μm is formed, and has a diameter of 120 ± 0.3 mm.
A recording layer containing a cyanine dye compound represented by the following general formula (I) is provided on the transparent disc-shaped substrate having a thickness of 0.6 ± 0.1 mm on the side where the pregroove is provided. , Or a track pitch of 0.6 to
0.9 μm pregroove formed, diameter 120
A recording layer containing a cyanine dye compound represented by the following general formula (I) on a side of the transparent disc-shaped substrate having a thickness of ± 0.3 mm and a thickness of 0.6 ± 0.1 mm provided with the pregroove: And a transparent disk-shaped protective substrate having the same shape as the disk-shaped substrate are joined together such that each recording layer is on the inside, and the thickness is 1.2 ± 0.2 mm. Heat mode type optical information recording medium: In the formula, DYE ⁺ represents a monovalent cyanine dye cation, n represents an integer of 1 or more, R ₅ and R ₆ each independently represent a substituent, and R ₇ and R ₈ each independently represent Represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group or a heterocyclic group, wherein R ₅ and R ₆ , R ₅ and R ₇ , R ₆ and R ₈ or R ₇ and R ₈ are each connected to each other; To form a ring, and r and s may be the same or different from each other. 7. The optical information recording medium according to claim 1, further comprising a metal light reflecting layer provided on the recording layer. 8. The optical information recording medium according to claim 1, wherein said optical information recording medium is 630 nm to 680.
An information recording method for recording information by irradiating a laser beam having a wavelength of nm.