JP2000158818A - Optical recording medium - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a write-once optical recording medium for carrying out a good recording and reproduction by using laser of 400-500 nm wavelength. SOLUTION: An optical recording medium is provided with at least a recording layer 2 and a reflection layer 3 on a base 1, and the recording layer 2 contains a benzobisoxa/thiazole compound represented by the formula, (in the formula, R1, R2, R3, R4, R5, R6, R7 and Z1, Z2, Z3 and Z4 represent respectively substituents described in the specification, and a ring A and ring B respectively and individually represent an oxazole ring or a thiazole ring).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an optical recording medium, and more particularly to a recordable optical recording medium containing a compound which can be recorded and reproduced by a blue laser beam.

[0002]

2. Description of the Related Art As an optical recording medium having a reflective layer on a substrate, a recordable CD-R (CD-Recordable) conforming to the compact disk (hereinafter abbreviated as CD) standard is used.
e) is widespread. CD-R recording capacity is 0.6
Although it is about 5 GB, with the dramatic increase in the amount of information, demands for higher density and larger capacity of information recording media are increasing.

[0003] By shortening the wavelength of a recording and reproducing laser, a beam spot can be reduced, and high-density optical recording can be performed. Recently, the development of short wavelength semiconductor lasers used in optical disk systems has been advanced,
Red semiconductor lasers of 0 nm, 650 nm and 635 nm have been put into practical use [for example, Nikkei Electronics, No. 592, p. 65, October 11, 1993]. DVDs using these semiconductor lasers and digitally recording moving images of 2 hours or more have been put to practical use. DV
Since D is a read-only medium, a write-once optical recording medium (DVD-R) corresponding to this capacity is also being developed.

[0004] Further, development of blue semiconductor lasers having a wavelength of 400 nm to 500 nm capable of recording at a very high density has been rapidly progressing [for example, Nikkei Electronics, N.
o. 708, p. 117, January 26, 1998 issue],
A write-once optical recording medium corresponding to this is also being developed.

When pits are formed by irradiating a laser beam to a recording layer of a write-once optical recording medium to cause a physical change or a chemical change in the recording layer, a pit having good optical constants and decomposition behavior of the compound is formed. It is an important factor to make it happen. Those that are difficult to decompose have reduced sensitivity, while those that are severely decomposed or are subject to change have a greater effect between pits and in the radial direction, making reliable pit formation difficult. Conventional CD-R media have a low refractive index of the recording layer at the wavelength of the blue semiconductor laser used in ultra-high density recording,
Since the extinction coefficient is not an appropriate value, good recording and recording can be achieved by lowering the reflectance, increasing the error rate, and increasing the jitter.
Cannot play. Therefore, it is necessary to select an appropriate compound having an optical property and a decomposition behavior for a blue semiconductor laser as the compound used for the recording layer. . However, examples of organic dye compounds actually proposed are described in JP-A-4-7469.
No. 0, JP-A-7-3042
There are only very limited examples such as the porphyrin compounds described in JP-A-56 or JP-A-7-304257.

[0006]

However, since cyanine dyes generally have low light fastness, regeneration may sometimes be impossible when the medium is stored for a long period of time. The porphyrin compounds described in the above publications are disclosed in
As described in the examples of JP-A-304256 or JP-A-7-304257, when the recording layer of the optical recording medium is used alone, it is impossible to write with a laser beam. It cannot be said that the compound used has sufficiently satisfactory performance. Further, in the optical recording medium disclosed in the publications, it is essential to use a mixture of a single molecule or a high molecular compound having a substituent coordinating with an organic dye.
Since the recording layer may become cloudy as in the sample disk described in the Example section of JP-A-7, the production of the medium is complicated, for example, the composition ratio needs to be set, and there is still room for the productivity structure. Was left. Therefore, there is an urgent need to develop a dye for an optical recording medium suitable for producing a medium having ultra-high density recording and excellent long-term storage stability.

[0007] The object of the present invention is to provide a wavelength of 400 nm to 500 nm.
An object of the present invention is to provide an optical recording medium having, in a recording layer, a compound suitable for ultra-high-density recording capable of excellent recording and reproduction with a laser beam selected from the range of nm.

[0008]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, completed the present invention. That is, the present invention relates to an optical recording medium having at least a recording layer and a reflective layer on a substrate, wherein the recording layer has the general formula (1)

[0009]

Embedded image

Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
R ⁷ and R ⁸ each independently represent a hydrogen atom, a halogen atom,
Cyano group, substituted or unsubstituted alkyl group, aralkyl group, aryl group, alkoxy group, aralkyloxy group,
Aryloxy, alkenyl, alkenyloxy, alkylthio, aralkylthio, arylthio, alkylamino, aralkylamino, arylamino, alkenylamino, acyl, alkoxycarbonyl, aralkyloxycarbonyl, aryl An oxycarbonyl group, an alkenyloxycarbonyl group, an alkylaminocarbonyl group, or a heterocyclic group, wherein ring A and ring B each independently represent an oxazole ring or a thiazole ring, and Z ¹ , Z ² , Z ³ , and Z ⁴ are Each independently represents a substituted or unsubstituted alkyl group, aralkyl group, alkenyl group, or aryl group. Alternatively, Z ¹ and Z ² , Z ³
And Z ⁴ may be linked together to form a ring. An optical recording medium containing a benzobisoxa / thiazole compound represented by the formula:
The present invention relates to a novel optical recording medium capable of recording and reproducing with respect to a laser beam selected from the range of (1).

[0011]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The concrete constitution of the present invention will be described below.

This optical recording medium has a four-layer structure in which a substrate, a recording layer, a reflective layer and a protective layer are sequentially laminated.
This may be used as a single plate as shown in FIG. 1 or may be bonded with an adhesive layer as in a DVD as shown in FIG.

The material of the substrate is basically required to be transparent at the wavelength of the recording light and the reproducing light. For example, an acrylic resin such as a polycarbonate resin, a vinyl chloride resin and polymethyl methacrylate, a polymer material such as a polystyrene resin and an epoxy resin, and an inorganic material such as glass are used.
These substrate materials are formed into a disk shape by injection molding or the like. If necessary, guide grooves or pits may be formed on the substrate surface. Such guide grooves and pits
It is desirable to apply it at the time of molding the substrate, but it can also be applied using an ultraviolet curable resin layer on the substrate.

In the present invention, a recording layer is provided on a substrate. The recording layer of the present invention contains a benzobisoxa / thiazole compound represented by the general formula (1).

The general formula (1) contained in the recording layer of the present invention
Specific examples of the benzobisoxa / thiazole compound represented by are described below in detail.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
As the group represented by R ⁶ , R ⁷ , and R ⁸ , a group having good workability by application to a polycarbonate, acrylic, epoxy, polyolefin substrate, or the like can be selected and used.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the groups represented by R ⁶ , R ⁷ , and R ⁸ include a halogen atom such as a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, or a cyano group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkyl group represented by R ⁶ , R ⁷ , and R ⁸ include a linear or branched or cyclic unsubstituted alkyl group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group, an acyl group, and an acyloxy group. , An alkoxycarbonyl group, an aryloxycarbonyl group, an aralkyloxycarbonyl group, an alkenyloxycarbonyl group, an alkoxycarbonyloxy group, a dialkylamino group, an acylamino group, an alkylsulfonamino group, an alkylsulfone group, and a heterocyclic group. Examples include an alkyl group substituted with a selected substituent.

The substituted or unsubstituted linear, branched or cyclic alkyl group includes a methyl group, an ethyl group, an n-
Propyl group, iso-propyl group, n-butyl group, is
o-butyl group, sec-butyl group, t-butyl group, n-
Pentyl group, iso-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclopentyl group, n-hexyl group, 4-methylpentyl group , 3-methylpentyl group, 2-methylpentyl group, 1
-Methylpentyl group, 3,3-dimethylbutyl group, 2,
3-dimethylbutyl group, 1,3-dimethylbutyl group,
2,2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 3-ethylbutyl group,
2-ethylbutyl group, 1-ethylbutyl group, 1,2,2
-Trimethylbutyl group, 1,1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, cyclohexyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group , 5-methylhexyl, 2,4-dimethylpentyl, n-octyl, 2-ethylhexyl, 2,5-dimethylhexyl, 2,5,5-trimethylpentyl, 2,4-dimethylhexyl A 2,2,4-trimethylpentyl group,
3,5,5-trimethylhexyl group, n-nonyl group, n
-Decyl group, 4-ethyloctyl group, 4-ethyl-4,
5-methylhexyl group, n-undecyl group, n-dodecyl group, 1,3,5,7-tetraethyloctyl group, 4-
Butyloctyl group, 6,6-diethyloctyl group, n-
Tridecyl group, 6-methyl-4-butyloctyl group, n
-Tetradecyl group, n-pentadecyl group, 3,5-dimethylheptyl group, 2,6-dimethylheptyl group, 2,4
C1-C15-free groups such as -dimethylheptyl group, 2,2,5,5-tetramethylhexyl group, 1-cyclopentyl-2,2-dimethylpropyl group, 1-cyclohexyl-2,2-dimethylpropyl group; A substituted alkyl group;

Chloromethyl group, chloroethyl group, bromoethyl group, iodoethyl group, dichloromethyl group, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2
C1-C10 alkyl groups substituted by halogen atoms such as 2-trichloroethyl group, 1,1,1,3,3,3-hexafluoro-2-propyl group, nonafluorobutyl group and perfluorodecyl group ;

2-hydroxyethyl group, 2-hydroxymethyl group, 4-hydroxyethyl group, 2-hydroxy-
3-methoxypropyl group, 2-hydroxy-3-chloropropyl group, 2-hydroxy-3-ethoxypropyl group, 3-butoxy-2-hydroxypropyl group, 2-hydroxy-3-cyclohexyloxypropyl group, 2-
Hydroxypropyl group, 2-hydroxybutyl group, 4-
A C 1-10 alkyl group substituted with a hydroxy group such as a hydroxydecalyl-2-oxy group;

Hydroxymethoxymethyl group, hydroxyethoxyethyl group, 2- (2'-hydroxy-1'-methylethoxy) -1-methylethyl group, 2- (3'-fluoro-2'-hydroxypropoxy) ethyl group , 2-
A hydroxyalkoxyalkyl group having 2 to 10 carbon atoms such as a (3'-chloro-2'-hydroxypropoxy) ethyl group, a hydroxybutoxycyclohexyloxy group;

A hydroxymethoxymethoxymethyl group, a hydroxyethoxyethoxyethyl group, [2 ′-(2′-
Hydroxy-1′-methylethoxy) -1′-methylethoxy] ethoxyethyl group, [2 ′-(2′-fluoro-
1'-hydroxyethoxy) -1'-methylethoxy]
A hydroxyalkoxyalkoxyalkyl group having 3 to 10 carbon atoms, such as an ethoxyethyl group, [2 ′-(2′-chloro-1′-hydroxyethoxy) -1′-methylethoxy] ethoxyethyl group;

Cyanomethyl group, 2-cyanoethyl group, 4
-Cyanoethyl group, 2-cyano-3-methoxypropyl group, 2-cyano-3-chloropropyl group, 2-cyano-
Alkyl having 2 to 10 carbon atoms substituted with a cyano group such as a 3-ethoxypropyl group, a 3-butoxy-2-cyanopropyl group, a 2-cyano-3-cyclohexylpropyl group, a 2-cyanopropyl group, or a 2-cyanobutyl group. Group;

Methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, n-hexyloxyethyl, 4-methylpentoxyethyl, 1,3-dimethylbutoxyethyl group, 2-ethylhexyloxyethyl group, n-octyloxyethyl group, 3,5,5-trimethylhexyloxyethyl group, 2-methyl-1-iso-propylpropoxyethyl group, 3- Methyl-1-iso-propylbutyloxyethyl group, 2-ethoxy-1-methylethyl group, 3-methoxybutyl group, 3,3,3-trifluoropropoxyethyl group, 3,3,3-trichloropropoxyethyl group 2-1 carbon atoms substituted with an alkoxy group such as
5 alkyl groups;

Methoxymethoxymethyl group, methoxyethoxyethyl group, ethoxyethoxyethyl group, propoxyethoxyethyl group, butoxyethoxyethyl group, cyclohexyloxyethoxyethyl group, decalyloxypropoxyethoxy group, 1,2-dimethylpropoxyethoxyethyl group , 3-methyl-1-iso-butylbutoxyethoxyethyl group, 2-methoxy-1-methylethoxyethyl group, 2-butoxy-1-methylethoxyethyl group, 2- (2′-ethoxy-1′-methylethoxy) )-
An alkoxyalkoxyalkyl group having 3 to 15 carbon atoms such as a 1-methylethyl group, a 3,3,3-trifluoropropoxyethoxyethyl group, a 3,3,3-trichloropropoxyethoxyethyl group;

Methoxymethoxymethoxymethyl group, methoxyethoxyethoxyethyl group, ethoxyethoxyethoxyethyl group, butoxyethoxyethoxyethyl group, cyclohexyloxy, propoxypropoxypropoxy group, 2,2,2-trifluoroethoxyethoxyethoxyethyl group, 2 An alkoxyalkoxyalkoxyalkyl group having 4 to 15 carbon atoms, such as a 2,2,2-trichloroethoxyethoxyethoxyethyl group;

A formylmethyl group, a 2-oxobutyl group,
3-oxobutyl group, 4-oxobutyl group, 1,3-dioxo-2-cyclohexyl group, 2-oxo-5-t-
An alkyl group having 2 to 10 carbon atoms substituted with an acyl group such as a butyl-1-cyclohexyl group;

Formyloxymethyl, acetoxyethyl, propionyloxyethyl, butanoyloxyethyl, valeryloxyethyl, 2-ethylhexanoyloxyethyl, 3,5,5-trimethylhexanoyloxyethyl An alkyl group having 2 to 15 carbon atoms, which is substituted with an acyloxy group such as, 3,5,5-trimethylhexanoyloxyhexyl group, 3-fluorobutyryloxyethyl group, 3-chlorobutyryloxyethyl group;

Formyloxymethoxymethyl group, acetoxyethoxyethyl group, propionyloxyethoxyethyl group, valeryloxyethoxyethyl group, 2-ethylhexanoyloxyethoxyethyl group, 3,5,5-trimethylhexanoyloxybutoxyethyl group , 3,
C3 to C1 substituted with an acyloxyalkoxy group such as a 5,5-trimethylhexanoyloxyethoxyethyl group, a 2-fluoropropionyloxyethoxyethyl group or a 2-chloropropionyloxyethoxyethyl group
5 alkyl groups;

Acetoxymethoxymethoxymethyl group, acetoxyethoxyethoxyethyl group, propionyloxyethoxyethoxyethyl group, valeryloxyethoxyethoxyethyl group, 2-ethylhexanoyloxyethoxyethoxyethyl group, 3,5,5-trimethylhexanoyl Oxyoxyethoxyethoxyethyl group, 2-fluoropropionyloxyethoxyethoxyethyl group,
An alkyl group having 5 to 15 carbon atoms substituted with an acyloxyalkoxyalkoxy group such as a 2-chloropropionyloxyethoxyethoxyethyl group;

Methoxycarbonylmethyl, ethoxycarbonylmethyl, butoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, butoxycarbonylethyl, p-ethylcyclohexyloxycarbonylcyclohexyl, 2,2
An alkyl group having 3 to 15 carbon atoms substituted with an alkoxycarbonyl group such as a 3,3-tetrafluoropropoxycarbonylmethyl group or a 2,2,3,3-tetrachloropropoxycarbonylmethyl group;

Phenoxycarbonylmethyl, phenoxycarbonylethyl, 4-t-butylphenoxycarbonylethyl, naphthyloxycarbonylmethyl,
An alkyl group having 8 to 15 carbon atoms substituted with an aryloxycarbonyl group such as a biphenyloxycarbonylethyl group;

An aralkyloxycarbonyl group having 9 to 15 carbon atoms, such as a benzyloxycarbonylmethyl group, a benzyloxycarbonylethyl group, a phenethyloxycarbonylmethyl group, a 4-cyclohexyloxybenzyloxycarbonylmethyl group;

An alkyl group having 4 to 10 carbon atoms substituted by an alkenyloxycarbonyl group such as a vinyloxycarbonylmethyl group, a vinyloxycarbonylethyl group, an allyloxycarbonylmethyl group and an octenoxycarbonylmethyl group;

Methoxycarbonyloxymethyl, methoxycarbonyloxyethyl, ethoxycarbonyloxyethyl, butoxycarbonyloxyethyl,
An alkyl group having 3 to 15 carbon atoms substituted with an alkoxycarbonyloxy group such as a 2,2,2-trifluoroethoxycarbonyloxyethyl group or a 2,2,2-trichloroethoxycarbonyloxyethyl group;

Methoxymethoxycarbonyloxymethyl group, methoxyethoxycarbonyloxyethyl group, ethoxyethoxycarbonyloxyethyl group, butoxyethoxycarbonyloxyethyl group, 2,2,2-trifluoroethoxyethoxycarbonyloxyethyl group, 2,
An alkyl group having 4 to 15 carbon atoms substituted with an alkoxyalkoxycarbonyloxy group such as a 2,2-trichloroethoxyethoxycarbonyloxyethyl group;

Dimethylaminomethyl, diethylaminomethyl, di-n-butylaminomethyl, di-n-hexylaminomethyl, di-n-octylaminomethyl, di-n-decylaminomethyl, N- Isoamyl-
N-methylaminomethyl group, piperidinomethyl group, di (methoxymethyl) aminomethyl group, di (methoxyethyl) aminomethyl group, di (ethoxymethyl) aminomethyl group, di (ethoxyethyl) aminomethyl group, di (propoxyethyl) ) Aminomethyl group, di (butoxyethyl)
Aminomethyl group, bis (2-cyclohexyloxyethyl) aminomethyl group; dimethylaminoethyl group, diethylaminoethyl group, di-n-butylaminoethyl group, di-n-hexylaminoethyl group, di-n-octylaminoethyl Group, di-n-decylaminoethyl group, N-isoamyl-N-methylaminoethyl group, piperidinoethyl group, di (methoxymethyl) aminoethyl group, di (methoxyethyl) aminoethyl group, di (ethoxymethyl) aminoethyl A di (ethoxyethyl) aminoethyl group, a di (propoxyethyl) aminoethyl group, a di (butoxyethyl) aminoethyl group, a bis (2-cyclohexyloxyethyl) aminoethyl group; a dimethylaminopropyl group, a diethylaminopropyl group, Di-n-butylaminopropyl group, di-n Hexyl aminopropyl group, di -
n-octylaminopropyl group, di-n-decylaminopropyl group, N-isoamyl-N-methylaminopropyl group, piperidinopropyl group, di (methoxymethyl) aminopropyl group, di (methoxyethyl) aminopropyl group Di (ethoxymethyl) aminopropyl group, di (ethoxyethyl) aminopropyl group, di (propoxyethyl) aminopropyl group, di (butoxyethyl) aminopropyl group, bis (2-cyclohexyloxyethyl) aminopropyl group; dimethyl Aminobutyl group, diethylaminobutyl group, di-n-butylaminobutyl group, di-n
-Hexylaminobutyl group, di-n-octylaminobutyl group, di-n-decylaminobutyl group, N-isoamyl-N-methylaminobutyl group, piperidinobutyl group,
Di (methoxymethyl) aminobutyl group, di (methoxyethyl) aminobutyl group, di (ethoxymethyl) aminobutyl group, di (ethoxyethyl) aminobutyl group, di (propoxyethyl) aminobutyl group, di (butoxyethyl) An alkyl group having 3 to 20 carbon atoms substituted by a dialkylamino group such as an aminobutyl group or a bis (2-cyclohexyloxyethyl) aminobutyl group;

Substitution with an acylamino group such as an acetylaminomethyl group, an acetylaminoethyl group, a propionylaminoethyl group, a butanoylaminoethyl group, a cyclohexanecarbonylaminoethyl group, a p-methylcyclohexanecarbonylaminoethyl group, and a succiniminoethyl group. An alkyl group having 3 to 10 carbon atoms;

An alkyl group having 2 to 10 carbon atoms substituted by an alkylsulfonamino group such as a methylsulfonaminomethyl group, a methylsulfonaminoethyl group, an ethylsulfonaminoethyl group, a propylsulfonaminoethyl group, an octylsulfonaminoethyl group;

A methylsulfonemethyl group, an ethylsulfonemethyl group, a butylsulfonemethyl group, a methylsulfonethyl group, an ethylsulfonethyl group, a butylsulfonethyl group, a 2-ethylhexylsulfonethyl group,
3,3-tetrafluoropropylsulfonmethyl group,
2 to 10 carbon atoms substituted with an alkylsulfone group such as a 2,2,3,3-tetrachloropropylsulfonmethyl group
An alkyl group of

A pyrrolinomethyl group, a pyrrolidinomethyl group,
Alkyl substituted with a heterocyclic group such as a pyrazolidinomethyl group, an imidazolidinomethyl group, an oxazolyl group, a triazolinomethyl group, a morpholinomethyl group, an indolinomethyl group, a benzimidazolinomethyl group, and a carbazolinomethyl group. And the like.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aralkyl groups represented by R ⁶ , R ⁷ , and R ⁸ are aralkyl groups having the same substituents as the above-mentioned alkyl groups, and are preferably a benzyl group or a nitrobenzyl group. , Cyanobenzyl group, hydroxybenzyl group, methylbenzyl group, trifluoromethylbenzyl group, naphthylmethyl group, nitronaphthylmethyl group, cyanonaphthylmethyl group, hydroxynaphthylmethyl group, methylnaphthylmethyl group, trifluoromethylnaphthylmethyl group, Examples thereof include an aralkyl group having 7 to 15 carbon atoms such as a fluoren-9-ylethyl group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aryl groups represented by R ⁶ , R ⁷ , and R ⁸ are aryl groups having the same substituents as the above-described alkyl groups, and are preferably a phenyl group or a nitrophenyl group. , Cyanophenyl, hydroxyphenyl, methylphenyl, trifluoromethylphenyl, naphthyl, nitronaphthyl, cyanonaphthyl, hydroxynaphthyl, methylnaphthyl, trifluoromethylnaphthyl, methoxycarbonylphenyl, 4 -(5'-methylbenzoxazole-2'-
Yl) aryl groups having 6 to 15 carbon atoms such as phenyl group and dibutylaminocarbonylphenyl group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkoxy groups represented by R ⁶ , R ⁷ and R ⁸ include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group and a tert-butoxy group. , Sec-butoxy group, n-pentyloxy group, isopentyloxy group, t
ert-pentyloxy group, sec-pentyloxy group, cyclopentyloxy group, n-hexyloxy group,
1-methylpentyloxy group, 2-methylpentyloxy group, 3-methylpentyloxy group, 4-methylpentyloxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethylbutoxy Group, 2,
3-dimethylbutoxy group, 1,1,2-trimethylpropoxy group, 1,2,2-trimethylpropoxy group, 1-
Ethyl butoxy group, 2-ethyl butoxy group, 1-ethyl-2-methylpropoxy group, cyclohexyloxy group,
Methylcyclopentyloxy group, n-heptyloxy group, 1-methylhexyloxy group, 2-methylhexyloxy group, 3-methylhexyloxy group, 4-methylhexyloxy group, 5-methylhexyloxy group, 1,1
-Dimethylpentyloxy group, 1,2-dimethylpentyloxy group, 1,3-dimethylpentyloxy group, 1,
4-dimethylpentyloxy group, 2,2-dimethylpentyloxy group, 2,3-dimethylpentyloxy group,
2,4-dimethylpentyloxy group, 3,3-dimethylpentyloxy group, 3,4-dimethylpentyloxy group, 1-ethylpentyloxy group, 2-ethylpentyloxy group, 3-ethylpentyloxy group, 1, 1,2-
Trimethylbutoxy group, 1,1,3-trimethylbutoxy group, 1,2,3-trimethylbutoxy group, 1,2,2
-Trimethylbutoxy group, 1,3,3-trimethylbutoxy group, 2,3,3-trimethylbutoxy group, 1-ethyl-1-methylbutoxy group, 1-ethyl-2-methylbutoxy group, 1-ethyl-3 -Methylbutoxy group, 2-ethyl-1-methylbutoxy group, 2-ethyl-3-methylbutoxy group, 1-n-propylbutoxy group, 1-isopropylbutoxy group, 1-isopropyl-2-methylpropoxy group, methyl Cyclohexyloxy group, n-octyloxy group, 1-methylheptyloxy group, 2-methylheptyloxy group, 3-methylheptyloxy group, 4-
Methylheptyloxy group, 5-methylheptyloxy group, 6-methylheptyloxy group, 1,1-dimethylhexyloxy group, 1,2-dimethylhexyloxy group,
1,3-dimethylhexyloxy group, 1,4-dimethylhexyloxy group, 1,5-dimethylhexyloxy group, 2,2-dimethylhexyloxy group, 2,3-dimethylhexyloxy group, 2,4-dimethyl Hexyloxy group, 2,5-dimethylhexyloxy group, 3,3-dimethylhexyloxy group, 3,4-dimethylhexyloxy group, 3,5-dimethylhexyloxy group, 4,4-
Dimethylhexyloxy group, 4,5-dimethylhexyloxy group, 1-ethylhexyloxy group, 2-ethylhexyloxy group, 3-ethylhexyloxy group, 4-ethylhexyloxy group, 1-n-propylpentyloxy group, 2-n -Propylpentyloxy group, 1-isopropylpentyloxy group, 2-isopropylpentyloxy group, 1-ethyl-1-methylpentyloxy group, 1
-Ethyl-2-methylpentyloxy group, 1-ethyl-
3-methylpentyloxy group, 1-ethyl-4-methylpentyloxy group, 2-ethyl-1-methylpentyloxy group, 2-ethyl-2-methylpentyloxy group, 2
-Ethyl-3-methylpentyloxy group, 2-ethyl-
4-methylpentyloxy group, 3-ethyl-1-methylpentyloxy group, 3-ethyl-2-methylpentyloxy group, 3-ethyl-3-methylpentyloxy group, 3
-Ethyl-4-methylpentyloxy group, 1,1,2-
Trimethylpentyloxy group, 1,1,3-trimethylpentyloxy group, 1,1,4-trimethylpentyloxy group, 1,2,2-trimethylpentyloxy group,
1,2,3-trimethylpentyloxy group, 1,2,4
A trimethylpentyloxy group, a 1,3,4-trimethylpentyloxy group, a 2,2,3-trimethylpentyloxy group, a 2,2,4-trimethylpentyloxy group,
2,3,4-trimethylpentyloxy group, 1,3,3
-A trimethylpentyloxy group, a 2,3,3-trimethylpentyloxy group, a 3,3,4-trimethylpentyloxy group, a 1,4,4-trimethylpentyloxy group,
2,4,4-trimethylpentyloxy group, 3,4,4
-Trimethylpentyloxy group, 1-n-butylbutoxy group, 1-isobutylbutoxy group, 1-sec-butylbutoxy group, 1-tert-butylbutoxy group, 2-t
tert-butylbutoxy group, 1-n-propyl-1-methylbutoxy group, 1-n-propyl-2-methylbutoxy group, 1-n-propyl-3-methylbutoxy group, 1-
Isopropyl-1-methylbutoxy group, 1-isopropyl-2-methylbutoxy group, 1-isopropyl-3-methylbutoxy group, 1,1-diethylbutoxy group, 1,2
-Diethylbutoxy group, 1-ethyl-1,2-dimethylbutoxy group, 1-ethyl-1,3-dimethylbutoxy group, 1-ethyl-2,3-dimethylbutoxy group, 2-ethyl-1,1-dimethyl Butoxy group, 2-ethyl-1,
2-dimethylbutoxy group, 2-ethyl-1,3-dimethylbutoxy group, 2-ethyl-2,3-dimethylbutoxy group, 1,2-dimethylcyclohexyloxy group, 1,3
-Dimethylcyclohexyloxy group, 1,4-dimethylcyclohexyloxy group, ethylcyclohexyloxy group, n-nonyloxy group, 3,5,5-trimethylhexyloxy group, n-decyloxy group, n-undecyloxy group, n- A carbon number of 1 to 15 such as a dodecyloxy group, a 1-adamantyloxy group, an n-pentadecanyloxy group;
Linear, branched or cyclic unsubstituted alkoxy groups;

Methoxymethoxy, methoxyethoxy, ethoxyethoxy, n-propoxyethoxy,
Isopropoxyethoxy group, n-butoxyethoxy group,
Isobutoxyethoxy group, tert-butoxyethoxy group, sec-butoxyethoxy group, n-pentyloxyethoxy group, isopentyloxyethoxy group, tert
-Pentyloxyethoxy group, sec-pentyloxyethoxy group, cyclopentyloxyethoxy group, n-hexyloxyethoxy group, ethylcyclohexyloxyethoxy group, n-nonyloxyethoxy group, 3,5,5
-Trimethylhexyloxyethoxy group, 3,5,5-
Trimethylhexyloxybutoxy group, n-decyloxyethoxy group, n-undecyloxyethoxy group, n-
Dodecyloxyethoxy group, 3-methoxypropoxy group, 3-ethoxypropoxy group, 3- (n-propoxy) propoxy group, 2-isopropoxypropoxy group,
2-methoxybutoxy group, 2-ethoxybutoxy group, 2
An alkoxy group having 2 to 15 carbon atoms, which is substituted with an alkoxy group, such as-(n-propoxy) butoxy group, 4-isopropoxybutoxy group, decalyloxyethoxy group, adamantyloxyethoxy group;

Methoxymethoxymethoxy, ethoxymethoxymethoxy, propoxymethoxymethoxy, butoxymethoxymethoxy, methoxyethoxymethoxy, ethoxyethoxymethoxy, propoxyethoxymethoxy, butoxyethoxymethoxy, methoxypropoxymethoxy, ethoxypropoxy Methoxy group,
Propoxypropoxymethoxy group, butoxypropoxymethoxy group, methoxybutoxymethoxy group, ethoxybutoxymethoxy group, propoxybutoxymethoxy group, butoxybutoxymethoxy group, methoxymethoxyethoxy group, ethoxymethoxyethoxy group, propoxymethoxyethoxy group, butoxymethoxyethoxy group, Methoxyethoxyethoxy group, ethoxyethoxyethoxy group, propoxyethoxyethoxy group, butoxyethoxyethoxy group, methoxypropoxyethoxy group, ethoxypropoxyethoxy group, propoxypropoxyethoxy group, butoxypropoxyethoxy group, methoxybutoxyethoxy group, methoxybutoxyethoxy group, methoxybutoxyethoxy group Propoxybutoxyethoxy, butoxybutoxyethoxy, methoxymethoxypropoxy , Ethoxy methoxypropoxy group,
Propoxymethoxypropoxy, butoxymethoxypropoxy, methoxyethoxypropoxy, ethoxyethoxypropoxy, propoxyethoxypropoxy, butoxyethoxypropoxy, methoxypropoxypropoxy, ethoxypropoxypropoxy, propoxypropoxy, butoxypropoxy, butoxypropoxy Methoxybutoxypropoxy group, ethoxybutoxypropoxy group, propoxybutoxypropoxy group, butoxybutoxypropoxy group, methoxymethoxybutoxy group, ethoxymethoxybutoxy group, propoxymethoxybutoxy group, butoxymethoxybutoxy group,
Methoxyethoxybutoxy group, ethoxyethoxybutoxy group, propoxysiethoxybutoxy group, butoxyethoxybutoxygo, methoxypropoxybutoxy group, ethoxypropoxybutoxy group, propoxypropoxybutoxy group, butoxypropoxybutoxy group, methoxybutoxybutoxy group, methoxybutoxybutoxy group, methoxybutoxybutoxy group , Propoxybutoxybutoxy, butoxybutoxybutoxy, 4-ethylcyclohexyloxyethoxyethoxy, (2-ethyl-1-hexyloxy) ethoxypropoxy, 4- (3,5,5-trimethylhexyloxybutoxyethoxy) Linear, branched or cyclic C3-C15 alkoxy groups substituted with alkoxyalkoxy groups;

Methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n-propoxycarbonylmethoxy, isopropoxycarbonylmethoxy, 4'-
An alkoxy group having 3 to 10 carbon atoms substituted with an alkoxycarbonyl group such as an ethylcyclohexyloxycarbonylmethoxy group;

An alkoxy group having 3 to 10 carbon atoms, which is substituted by an acyl group such as an acetylmethoxy group, an ethylcarbonylmethoxy group and an octylcarbonylmethoxy group;

An acetyloxymethyl group, acetyloxyethyl group, acetyloxyhexyloxy group, butanoyloxycyclohexyloxy group, etc.
An alkoxy group substituted with an acyloxy group;

2-dimethylaminomethoxy, 2-dimethylaminoethoxy, 2- (2-dimethylaminoethoxy) ethoxy, 4-dimethylaminobutoxy, 1
-Dimethylaminopropan-2-yloxy group, 3-dimethylaminopropoxy group, 2-dimethylamino-2-
A methylpropoxy group, a 2-diethylaminoethoxy group,
2- (2-diethylaminoethoxy) ethoxy group, 3-
Diethylaminopropoxy group, 1-diethylaminopropoxy group, 2-diisopropylaminoethoxy group, 2-
C3-C15 substituted by a dialkylamino group, such as a (di-n-butylamino) ethoxy group, a 2-piperidylethoxy group, or a 4- (di-n-hexylamino) propyl group.
An alkoxy group of

Carbon substituted with a dialkylaminoalkoxy group such as a dimethylaminomethoxymethoxy group, a dimethylaminoethoxyethoxy group, a dimethylaminoethoxypropoxy group, a diethylaminoethoxypropoxy group, and a 4- (2'-diisobutylaminopropoxy) butoxyoxy group. An alkoxy group of formulas 4 to 15;

2-methylthiomethoxy group, 2-methylthioethoxy group, 2-ethylthioethoxy group, 2-n-propylthioethoxy group, 2-isopropylthioethoxy group, 2-n-butylthioethoxy group, 2-isobutyl An alkoxy group having 2 to 15 carbon atoms, which is substituted by an alkylthio group, such as a thioethoxy group and a 3,5,5-trimethylhexyloxyhexyloxy group; and the like, preferably a methoxy group, an ethoxy group, and an n-propoxy group. Group, is
o-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, t-butoxy group, n-pentoxy group, iso-pentoxy group, neopentoxy group, 2
-Methylbutoxy group, 2-ethylhexyloxy group,
Examples thereof include an alkoxy group having 1 to 10 carbon atoms such as a 3,5,5-trimethylhexyloxy group and a decalyl group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aralkyloxy groups represented by R ⁶ , R ⁷ , and R ⁸ are aralkyloxy groups having the same substituents as the above-described alkyl groups, and are preferably a benzyloxy group, Nitrobenzyloxy group, cyanobenzyloxy group, hydroxybenzyloxy group,
Methylbenzyloxy group, trifluoromethylbenzyloxy group, naphthylmethoxy group, nitronaphthylmethoxy group, cyanonaphthylmethoxy group, hydroxynaphthylmethoxy group, methylnaphthylmethoxy group, trifluoromethylnaphthylmethoxy group, fluoren-9-ylethoxy group, etc. And an aralkyloxy group having 7 to 15 carbon atoms.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aryloxy groups represented by R ⁶ , R ⁷ and R ⁸ are aryloxy groups having the same substituents as the above-mentioned alkyl groups, and are preferably phenoxy groups, And aryloxy groups having 6 to 10 carbon atoms such as -methylphenoxy group, 4-methylphenoxy group, 4-t-butylphenoxy group, 2-methoxyphenoxy group, 4-iso-propylphenoxy group, and naphthoxy group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkenyl groups represented by R ⁶ , R ⁷ and R ⁸ are alkenyl groups having the same substituents as the above-mentioned alkyl groups, and are preferably a vinyl group, a propenyl group, 1-butenyl group, iso-butenyl group, 1-pentenyl group, 2-pentenyl group, 2-methyl-1-butenyl group, 3-methyl-1-butenyl group, 2-
A methyl-2-butenyl group, a 2,2-dicyanovinyl group,
2-cyano-2-methylcarboxylvinyl group, 2-cyano-2-methylsulfonevinyl group, styryl group, 4-
An alkenyl group having 2 to 10 carbon atoms such as a phenyl-2-butenyl group is exemplified.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkenyloxy groups represented by R ⁶ , R ⁷ and R ⁸ are alkenyloxy groups having the same substituents as the above-mentioned alkyl groups, and are preferably a vinyloxy group or a propenyl group. Oxy group, 1-butenyloxy group, iso-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group, 2-methyl-
1-butenyloxy group, 3-methyl-1-butenyloxy group, 2-methyl-2-butenyloxy group, 2,2-dicyanovinyloxy group, 2-cyano-2-methylcarboxylvinyloxy group, 2-cyano-2- Methylsulfonvinyloxy group, styryloxy group, 4-phenyl-
An alkenyloxy group having 2 to 10 carbon atoms such as 2-butenyloxy group is exemplified.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkylthio groups represented by R ⁶ , R ⁷ , and R ⁸ are alkylthio groups having the same substituents as the above-described alkyl groups, and are preferably a methylthio group, an ethylthio group, n-propylthio group, is
o-propylthio group, n-butylthio group, iso-butylthio group, sec-butylthio group, t-butylthio group,
n-pentylthio group, iso-pentylthio group, neopentylthio group, 2-methylbutylthio group, methylcarboxylethylthio group, 2-ethylhexyl group, 3,5
Examples thereof include an alkylthio group having 1 to 10 carbon atoms such as a 5-trimethylhexylthio group and a decalylthio group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aralkylthio groups represented by R ⁶ , R ⁷ and R ⁸ are aralkylthio groups having the same substituents as the above-mentioned alkyl groups, preferably benzylthio group and nitro Benzylthio, cyanobenzylthio, hydroxybenzylthio, methylbenzylthio, trifluoromethylbenzylthio, naphthylmethylthio, nitronaphthylmethylthio, cyanonaphthylmethylthio, hydroxynaphthylmethylthio, methylnaphthylmethylthio, Examples thereof include an aralkylthio group having 7 to 15 carbon atoms such as a trifluoromethylnaphthylmethylthio group and a fluoren-9-ylethylthio group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted arylthio groups represented by R ⁶ , R ⁷ and R ⁸ are arylthio groups having the same substituents as the above-mentioned alkyl groups, and are preferably phenylthio group and 4-methylphenyl Examples thereof include an arylthio group having 6 to 10 carbon atoms such as a thio group, a 2-methoxyphenylthio group, a 4-t-butylphenylthio group, and a naphthylthio group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkylamino group represented by R ⁶ , R ⁷ , and R ⁸ include an alkylamino group having the same substituent as the above-described alkyl group, preferably a methylamino group, Ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, cyclohexylamino group, 3,
A monoalkylamino group having 1 to 10 carbon atoms such as a 5,5-trimethylhexylamino group, a nonylamino group, a decylamino group, a dimethylamino group, a diethylamino group,
Examples thereof include dialkylamino groups having 2 to 10 carbon atoms such as a methylethylamino group, a butylamino group, a piperidino group, a morpholino group, a di (acetyloxyethyl) amino group, and a di (propionyloxyethyl) amino group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aralkylamino groups represented by R ⁶ , R ⁷ , and R ⁸ are aralkylamino groups having the same substituents as the above-mentioned alkyl groups, preferably a benzylamino group, 7 carbon atoms such as phenethylamino, 3-phenylpropylamino, 4-ethylbenzylamino, 4-isopropylbenzylamino, etc.
Diaralkylamino group having 14 to 20 carbon atoms such as monoaralkylamino group having 10 to 10, dibenzylamino group, diphenethylamino group, bis (4-ethylbenzyl) amino group, bis (4-isopropylbenzyl) amino group; Is mentioned.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted arylamino groups represented by R ⁶ , R ⁷ and R ⁸ are arylamino groups having the same substituents as the above-mentioned alkyl groups, preferably an anilino group, naphthyl Amino group, toluidino group, xylidino group, ethylphenylamino group, isopropylphenylamino group, methoxyphenylamino group, ethoxyethylamino group, chloroanilino group, acetylanilino group, methoxycarbonylanilino group, ethoxycarbonylanilino group, propoxy Such as a carbonylanilino group,
Examples thereof include diarylamino groups having 12 to 14 carbon atoms such as monoarylamino groups having 6 to 10 carbon atoms, diphenylamino groups, ditolylamino groups, and N-phenyl-N-tolylamino groups.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkenylamino groups represented by R ⁶ , R ⁷ and R ⁸ are alkenylamino groups having the same substituents as the above-mentioned alkyl groups, preferably an allylamino group or a butenylamino group. Group, pentenylamino group, hexenylamino group, cyclohexenylamino group, octadienylamino group, monoalkenylamino group having 3 to 10 carbon atoms such as adamantenylamino group, diallylamino group, dibutenylamino group, dipentenylamino group, A dialkenylamino group having 6 to 12 carbon atoms such as a dihexenylamino group is exemplified.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted acyl groups represented by R ⁶ , R ⁷ , and R ⁸ are acyl groups having the same substituents as the above-mentioned alkyl groups, and are preferably a formyl group, a methylcarbonyl group. , Ethylcarbonyl group, n-propylcarbonyl group, iso-propylcarbonyl group, n-butylcarbonyl group, iso-butylcarbonyl group, se
c-butylcarbonyl group, t-butylcarbonyl group, n
-Pentylcarbonyl group, iso-pentylcarbonyl group, neopentylcarbonyl group, 2-methylbutylcarbonyl group, phenacyl group, methylphenacyl group, ethylphenacyl group, tolylcarbonyl group, propylphenacyl group, 4-t-butylphenacyl And a nitrobenzylcarbonyl group, a 3-butoxy-2-naphthoyl group, a cinnamoyl group and the like.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkoxycarbonyl groups represented by R ⁶ , R ⁷ and R ⁸ are alkoxycarbonyl groups having the same substituents as the above-mentioned alkyl groups, and are preferably methoxycarbonyl groups and ethoxy groups. Carbonyl group, n-propoxycarbonyl group, iso-propoxycarbonyl group, n-butoxycarbonyl group, iso
-Butoxycarbonyl group, sec-butoxycarbonyl group, t-butoxycarbonyl group, n-pentoxycarbonyl group, iso-pentoxycarbonyl group, neopentoxycarbonyl group, 2-pentoxycarbonyl group, 2-
Examples thereof include an alkoxycarbonyl group having 2 to 10 carbon atoms such as an ethylhexyloxycarbonyl group, a 3,5,5-trimethylhexyloxycarbonyl group, and a cyclohexyloxycarbonyl group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aralkyloxycarbonyl groups represented by R ⁶ , R ⁷ and R ⁸ are aralkyloxycarbonyl groups having the same substituents as the above-mentioned alkyl groups, preferably benzyloxy. Carbonyl, nitrobenzyloxycarbonyl, cyanobenzyloxycarbonyl, hydroxybenzyloxycarbonyl, methylbenzyloxycarbonyl, trifluoromethylbenzyloxycarbonyl, naphthylmethoxycarbonyl, nitronaphthylmethoxycarbonyl, cyanonaphthylmethoxycarbonyl Groups, hydroxynaphthylmethoxycarbonyl group, methylnaphthylmethoxycarbonyl group, trifluoromethylnaphthylmethoxycarbonyl group, fluoren-9-ylethoxycarbonyl group, etc. Number 8-15 aralkyloxycarbonyl groups such like.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted aryloxycarbonyl groups represented by R ⁶ , R ⁷ and R ⁸ are aryloxycarbonyl groups having the same substituents as the above-mentioned aryl groups, and preferably phenoxycarbonyl Group, 2-
Methylphenoxycarbonyl group, 4-methylphenoxycarbonyl group, 4-t-butylphenoxycarbonyl group, 2-methoxyphenoxycarbonyl group, 4-iso
And aryloxycarbonyl groups having 7 to 11 carbon atoms, such as -propylphenoxycarbonyl group and naphthoxycarbonyl group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkenyloxycarbonyl groups represented by R ⁶ , R ⁷ and R ⁸ are alkenyloxycarbonyl groups having the same substituents as the above-mentioned alkyl groups, and are preferably vinyloxy Carbonyl group, propenyloxycarbonyl group, 1-butenyloxycarbonyl group, iso-butenyloxycarbonyl group, 1-pentenyloxycarbonyl group, 2-pentenyloxycarbonyl group, 2-methyl-1-butenyloxycarbonyl group, 3-methyl-1-butenyloxycarbonyl group, 2-methyl-2-butenyloxycarbonyl group, 2,2-dicyanovinyloxycarbonyl group, 2-
A carbon number of 3 to 1 such as a cyano-2-methylcarboxylvinyloxycarbonyl group, a 2-cyano-2-methylsulfonevinyloxycarbonyl group, a styryloxycarbonyl group, a 4-phenyl-2-butenyloxycarbonyl group;
And one alkenyloxycarbonyl group.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted alkylaminocarbonyl groups represented by R ⁶ , R ⁷ , and R ⁸ include an alkylaminocarbonyl group having the same substituent as the above-described alkyl group, and preferably methylaminocarbonyl Group, ethylaminocarbonyl group, propylaminocarbonyl group,
Butylaminocarbonyl group, pentylaminocarbonyl group, hexylaminocarbonyl group, heptylaminocarbonyl group, octylaminocarbonyl group, nonylaminocarbonyl group, 3,5,5-trimethylhexylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, etc. Monoalkylaminocarbonyl group having 2 to 10 carbon atoms; dimethylaminocarbonyl group, diethylaminocarbonyl group, dipropylaminocarbonyl group, dibutylaminocarbonyl group, dipentylaminocarbonyl group, dihexylaminocarbonyl group, diheptylaminocarbonyl group, dioctylamino 3 to 2 carbon atoms such as a carbonyl group, a piperidinocarbonyl group, a morpholinocarbonyl group, a 4-methylpiperazinocarbonyl group, and a 4-ethylpiperazinocarbonyl group. Include dialkylaminocarbonyl groups of.

In the formula (1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
Examples of the substituted or unsubstituted heterocyclic group represented by R ⁶ , R ⁷ , and R ⁸ include a heterocyclic group having the same substituent as the above-mentioned alkyl group, preferably a furanyl group, a pyrrolyl group. Group, 3-pyrrolino group, pyrrolidino group, 1,3-oxolanyl group, pyrazolyl group, 2-pyrazolinyl group, pyrazolidinyl group, imidazolyl group, oxazolyl group, thiazolyl group, 1,2,3-oxadiazolyl group, 1,
2,3-triazolyl group, 1,2,4-triazolyl group, 1,3,4-thiadiazolyl group, 4H-pyranyl group, pyridinyl group, piperidinyl group, dioxanyl group,
Morpholinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, piperazinyl group, triazinyl group, benzofuranyl group, indolyl group, thionaphthenyl group, benzimidazolyl group, benzothiazolyl group, purinyl group,
Quinolinyl group, isoquinolinyl group, coumarinyl group, cinnolinyl group, quinoxalinyl group, dibenzofuranyl group,
An unsubstituted heterocyclic group such as a carbazolyl group, a phenanthronylyl group, a phenothiazinyl group, a flavonyl group;

Halogen, cyano; methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, methoxymethyl, ethoxyethyl, ethoxyethyl, trifluoroethyl Alkyl group such as methyl group; aralkyl group such as benzyl group and phenethyl group; aryl group such as phenyl group, tolyl group, naphthyl group, xylyl group, mesyl group, chlorophenyl group and methoxyphenyl group; methoxy group, ethoxy group and propoxy group Group, butoxy group, pentoxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, 2-ethylhexyl group, alkoxy group such as 3,5,5-trimethylhexyloxy group; benzyloxy group, Aralkyl groups such as phenethyloxy groups; Aryloxy groups such as xy group, tolyloxy group, naphthoxy group, xylyloxy group, mesyloxy group, chlorophenoxy group and methoxyphenoxy group; alkenyl groups such as vinyl group, allyl group, butenyl group, butadienyl group, pentenyl group and octenyl group; Alkenyloxy groups such as vinyloxy group, allyloxy group, butenyloxy group, butadienyloxy group, pentenyloxy group, octenyloxy group; methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, heptylthio group, Alkylthio groups such as octylthio, decylthio, methoxymethylthio, ethoxyethylthio, ethoxyethylthio, and trifluoromethylthio; aralkylthio such as benzylthio and phenethylthio; Niruchio group,
Arylthio groups such as tolylthio group, naphthylthio group, xylylthio group, mesylthio group, chlorophenylthio group and methoxyphenylthio group; dialkylamino groups such as dimethylamino group, diethylamino group, dipropylamino group and dibutylamino group; acetyl group and propionyl An acyl group such as a methoxycarbonyl group or an ethoxycarbonyl group; an aralkyloxycarbonyl group such as a benzyloxycarbonyl group or a phenethyloxycarbonyl group; a phenoxycarbonyl group, a tolyloxycarbonyl group, or a naphthoxycarbonyl group Aryloxycarbonyl groups such as a group, a xylyloxycarbonyl group, a mesyloxycarbonyl group, a chlorophenoxycarbonyl group, a methoxyphenoxycarbonyl group; vinyloxy Alkenyloxycarbonyl groups such as rubonyl group, allyloxycarbonyl group, butenyloxycarbonyl group, butadienyloxycarbonyl group, pentenyloxycarbonyl group, octenyloxycarbonyl group; methylaminocarbonyl group, ethylaminocarbonyl group, propylamino Carbonyl group, butylaminocarbonyl group, pentylaminocarbonyl group, hexylaminocarbonyl group, heptylaminocarbonyl group, octylaminocarbonyl group, nonylaminocarbonyl group, 3,5,5-trimethylhexylaminocarbonyl group, 2-ethylhexylaminocarbonyl A monoalkylaminocarbonyl group having 2 to 10 carbon atoms such as a group, a dimethylaminocarbonyl group, a diethylaminocarbonyl group,
Dipropylaminocarbonyl group, dibutylaminocarbonyl group, dipentylaminocarbonyl group, dihexylaminocarbonyl group, diheptylaminocarbonyl group, dioctylaminocarbonyl group, piperidinocarbonyl group, morpholinocarbonyl group, 4-methylpiperazinocarbonyl group An alkylaminocarbonyl group such as a dialkylaminocarbonyl group having 3 to 19 carbon atoms such as a 4-, 4-ethylpiperazinocarbonyl group; a furanyl group, a pyrrolyl group,
-Pyrrolino, pyrrolidino, 1,3-oxolanyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, imidazolyl, oxazolyl, thiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl Group, 1,2,4-triazolyl group, 1,3
4-thiadiazolyl group, 4H-pyranyl group, pyridinyl group, piperidinyl group, dioxanyl group, morpholinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group,
Piperazinyl group, triazinyl group, benzofuranyl group,
Indolyl group, thionaphthenyl group, benzimidazolyl group, benzothiazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, coumarinyl group, cinnolinyl group, quinoxalinyl group, dibenzofuranyl group, carbazolyl group, phenanthronylyl group, phenothiazinyl group,
Heterocyclic groups such as flavonyl groups; and heterocyclic groups substituted with substituents such as.

In the formula (1), ring A and ring B are each independently an oxazole ring or a thiazole ring.

[0074]

Embedded image

Or the formula (3)

[0076]

Embedded image [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , Z
¹ , Z ² , Z ³ , and Z ⁴ represent R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , Z ¹ , Z ² , Z ³ , and Z ⁴ represent the same meaning, and X ¹ and X ² each independently represent an oxygen atom or a sulfur atom. Represent. ] The compound shown by these.

In the formula (1), Z¹, Z^Two, Z^Three, Z^FourIndicated by
Substituted or unsubstituted alkyl, aralkyl,
As the kenyl group and the aryl group, R in formula (1)¹,
R^Two, R ^Three, R^Four, R^Five, R⁶, R⁷, R⁸Archi indicated by
An alkyl group identical to the R group; R in the formula (1)¹, R^Two,
R^Three, R^Four, R^Five, R⁶, R⁷, R⁸Aralkyl group represented by
An aralkyl group identical to the above; R in the formula (1)¹, R^Two, R^Three,
R^Four, R^Five, R⁶, R⁷, R⁸Same as the alkenyl group represented by
One alkenyl group; R in the formula (1)¹, R^Two, R^Three, R^Four,
R^Five, R⁶, R⁷, R⁸An ant identical to the aryl group represented by
A hydroxyl group;

Further, Z ¹ and Z ² and Z ³ and Z ⁴ may be connected to each other to form the following ring.

[0079]

Embedded image

As a specific example, the following carbon number 4-1
And 3 rings.

[0081]

Embedded image

Further, -CH = which bonds the anilino residue represented by the structure in the formula (1) to the ring A or the ring B at both ends.
The CH- group may have any of the trans or cis geometric isomerism.

As a method for synthesizing the benzobisoxa / thiazole compound represented by the general formula (1) of the present invention, for example, the formula (4) and / or the formula (5)

[0084]

Embedded image

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
R ⁷ , R ⁸ , Z ¹ , Z ² , Z ³ , and Z ⁴ represent R ¹ ,
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , Z ¹ , Z ² , Z ³ ,
It represents the same meaning as Z ^4. Carboxylic acid represented by 1,
3-dimethylimidazolidin-2-one, or 1-
In an amide solvent such as methyl-2-pyrrolidone, after reacting with thionyl chloride or the like to form an acid chloride,
2,5-diaminohydroquinone and / or its hydrochloride or sulfate, 2,5-diaminophenylene-1,4-dithiol and / or its hydrochloride or sulfate, or 2,5-diaminophenylene-4-hydroxy- The compound of formula (2) can be easily obtained by reacting with 1-thiophenol and / or its hydrochloride or sulfate, and the carboxylic acid of formula (4) and / or (5) In an amide solvent such as 1,3-dimethylimidazolidin-2-one or 1-methyl-2-pyrrolidone, thionyl chloride or the like is allowed to act to form an acid chloride, and then 4,6-diaminoresorcinol and / Or its hydrochloride or sulfate, 4,6-diaminophenylene-
By reacting with 1,3-dithiol and / or its hydrochloride or sulfate, or 4,6-diaminophenylene-3-hydroxy-1-thiophenol and / or its hydrochloride or sulfate, the compound of the formula (3) Can be easily obtained.

Further, the carboxylic acid represented by the formula (4) is converted into an amide solvent such as 1,3-dimethylimidazolidin-2-one or 1-methyl-2-pyrrolidone.
After forming an acid chloride by the action of thionyl chloride or the like, 2,5-diaminohydroquinone and / or its hydrochloride or sulfate, 2,5-diaminophenylene-1,4
-Dithiol and / or its hydrochloride or sulfate, or 2,5-diaminophenylene-4-hydroxy-1
Reacting with thiophenol and / or its hydrochloride or sulfate to form a compound of formula (6)

[0087]

Embedded image [R ^1, R ^2, R ³ in the ^{formula, R 4, Z 1, Z} 2 is, R ¹ in the formula ^{(1), R 2, R} 3, R 4, Z 1, Z 2 same meaning and And X
^1, X ² represent the same meaning as X ^1, X ² of formula (2). Or 4,6-diaminoresorcinol and / or its hydrochloride or sulfate, 4,6-diaminophenylene-1,3-dithiol and / or its hydrochloric acid By reacting with a salt or a sulfate, or 4,6-diaminophenylene-3-hydroxy-1-thiophenol and / or its hydrochloride or sulfate, the compound of the formula (7)

[0088]

Embedded image [Wherein R ¹ , R ² , R ³ , R ⁴ , Z ¹ , Z ² , Z ³ , Z ⁴ are
R ¹ , R ² , R ³ , R ⁴ , Z ¹ , Z ² , Z ³ , Z ^{4 in the} formula (1)
And show the same meaning, X ^1, X ² represent the same meaning as X ^1, X ² of formula (3). And the carboxylic acid represented by the formula (5) is converted to 1,3-dimethylimidazolidin-2-
The compound of formula (1) can also be obtained by reacting an acid chloride obtained by the action of thionyl chloride or the like in an amide solvent such as on or 1-methyl-2-pyrrolidone.

Here, with respect to the compound of the formula (3), the compound of the formula (8) and / or the formula (9)

[0090]

Embedded image [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , Z
¹ , Z ² , Z ³ , and Z ⁴ represent R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , Z ¹ , Z ² , Z ³ and Z ⁴ have the same meaning. The aldehyde represented by the formula (10) is prepared by using a catalytic amount of a base compound such as piperidine in an alcoholic solvent such as ethanol and propanol.

[0091]

Embedded image Wherein, X ^1, X ² represents the same meaning as X ^1, X ² of formula (3). The compound can be easily obtained by reacting with a quinone compound represented by the following formula:

Specific examples of the benzobisoxa / thiazole compound represented by the general formula (1) include those of the compounds (1-1) to (1-132) shown in Table 1.

[0093]

[Table 1]

[0094]

[Table 2]

[0095]

[Table 3]

[0096]

[Table 4]

[0097]

[Table 5]

[0098]

[Table 6]

[0099]

[Table 7]

[0100]

[Table 8]

[0101]

[Table 9]

[0102]

[Table 10]

[0103]

[Table 11]

[0104]

[Table 12]

[0105]

[Table 13]

[0106]

[Table 14]

[0107]

[Table 15]

[0108]

[Table 16]

[0109]

[Table 17]

[0110]

[Table 18]

[0111]

[Table 19]

[0112]

[Table 20]

[0113]

[Table 21]

[0114]

[Table 22]

[0115]

[Table 23]

[0116]

[Table 24]

[0117]

[Table 25]

[0118]

[Table 26]

[0119]

[Table 27]

[0120]

[Table 28]

[0121]

[Table 29]

Further, in order to improve the recording characteristics, etc., it has an absorption maximum at a wavelength of 350 nm to 550 nm,
You may mix with compounds other than the above which have a large refractive index in 500 nm. Specifically, cyanine compounds, squarylium-based compounds, naphthoquinone-based compounds, anthraquinone-based compounds, tetrapyraporphyrazine-based compounds, indophenol-based compounds, pyrylium-based compounds, thiopyrylium-based compounds, azurenium-based compounds, triphenylmethane-based compounds, There are a xanthene compound, an indasulen compound, an indigo compound, a thioindigo compound, a merocyanine compound, a thiazine compound, an acridine compound, an oxazine compound, a dipyrromethene compound, and the like, and a mixture of a plurality of compounds may be used. . The mixing ratio of these compounds is about 0.1 to 30%.

When forming a recording layer, a quencher, a compound thermal decomposition accelerator, an ultraviolet absorber, an adhesive, or the like may be mixed with the above-described compound, if necessary, or may have such an effect. It is also possible to introduce the compound as a substituent of the compound.

Specific examples of the quencher include acetylacetonate-based, bisdithio-α-diketone-based and bisphenyldithiol-based bisdithiol-based, thiocateconal-based, salicylaldehyde oxime-based, and thiobisphenolate-based. Metal complexes are preferred. Also, amines are suitable.

The compound thermal decomposition accelerator is not particularly limited as long as it can confirm the promotion of thermal decomposition of the compound by thermal weight loss analysis (TG analysis). For example, a metal-based anti-knocking agent, a metallocene compound And metal compounds such as acetylacetonate-based metal complexes. Examples of the metal anti-knocking agent include tetraethyl lead, other lead compounds, and Simantrene [Mn (C ₅ H ₅ ) (CO)
Examples of Mn-based compounds such as [ ₃ ] and metallocene compounds include iron biscyclopentadienyl complex (ferrocene), Ti, V, Mn, Cr, Co, Ni, M
o, Ru, Rh, Zr, Lu, Ta, W, Os, Ir,
There are biscyclopentadienyl complexes such as Sc and Y.
Among them, ferrocene, ruthenocene, osmocene, nickelocene, titanocene and derivatives thereof have good thermal decomposition promoting effects.

Other iron-based metal compounds include metallocene, organic iron compounds such as iron formate, iron oxalate, iron laurate, iron naphthenate, iron stearate, and iron acetate; iron acetylacetonate complex; Phenanthroline iron complex, bispyridine iron complex, ethylenediamine iron complex,
Iron complexes such as iron complexes of ethylenediaminetetraacetate, iron complexes of diethylenetriamine, iron complexes of diethyleneglycol dimethylether, iron complexes of diphosphino, iron complexes of dimethylglyoximate, iron complexes such as carbonyl iron complexes, cyanoiron complexes and ammineiron complexes, Examples thereof include iron halides such as iron, ferric chloride, ferrous bromide, and ferric bromide; inorganic iron salts such as iron nitrate and iron sulfate; and iron oxide. The thermal decomposition accelerator used here is desirably one that is soluble in an organic solvent and has good wet heat resistance and light resistance.

The various quencher and the compound thermal decomposition accelerator described above may be used singly or as a mixture of other types as required.

Further, if necessary, additives such as a binder, a leveling agent and an antifoaming agent may be added. 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.

When forming a recording layer on a substrate, in order to improve the solvent resistance, reflectance, recording sensitivity, etc. of the substrate,
A layer made of an inorganic substance or a polymer may be provided on the substrate.

Here, the content of the compound represented by the general formula (1) in the recording layer is 30% or more, preferably 60% or more.
% Or more. In addition, it is also preferable that it is substantially 100%.

The method for providing the recording layer includes, for example, a coating method such as a spin coating method, a spraying method, a casting method, and an immersion method, a sputtering method, a chemical vapor deposition method, and a vacuum vapor deposition method. Is preferred.

When a coating method such as a spin coating method is used, the compound represented by the general formula (1) is dissolved or dispersed in a solvent so as to be 1 to 40% by weight, preferably 3 to 30% by weight. A coating solution is used, and at this time, it is preferable to select a solvent that does not damage the substrate.
For example, methanol, ethanol, isopropyl alcohol, octafluoropentanol, allyl alcohol, methyl cellosolve, ethyl cellosolve, alcohol solvents such as tetrafluoropropanol, hexane,
Aliphatic or alicyclic hydrocarbon solvents such as heptane, octane, decane, cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane,
Aromatic hydrocarbon solvents such as toluene, xylene and benzene, halogenated hydrocarbon solvents such as carbon tetrachloride, chloroform, tetrachloroethane and dibromoethane,
Ether solvents such as diethyl ether, dibutyl ether, diisopropyl ether and dioxane; ketone solvents such as acetone and 3-hydroxy-3-methyl-2-butanone; ester solvents such as ethyl acetate and methyl lactate; and water. Can be These may be used alone or in combination. If necessary, the compound of the recording layer can be used by dispersing it in a polymer thin film or the like.

If a solvent that does not damage the substrate cannot be selected, a sputtering method, a chemical vapor deposition method, a vacuum vapor deposition method, or the like is effective.

The thickness of the recording layer is 30 nm to 1000 nm.
However, it is preferably 50 nm to 300 nm. If the thickness of the recording layer is less than 50 nm, recording may not be performed due to large thermal diffusion, or a recording signal may be distorted and the signal amplitude may be reduced. The thickness is 300 nm.
If the thickness is larger, the reflectance may decrease, and the reproduction signal characteristics may deteriorate.

Next, on the recording layer, preferably 50 nm to
A reflective layer having a thickness of 300 nm is formed. A reflection amplification layer or an adhesive layer can be provided between the recording layer and the reflection layer in order to increase the reflectance and improve the adhesion. As a material of the reflection layer, a material having sufficiently high reflectance at the wavelength of the reproduction light, for example, Au, Al, Ag, Cu, Ti, Cr, Ni, P
The metals t, Ta, Cr and Pd can be used alone or as an alloy. Among them, Au, Al,
Ag has a high reflectance and is suitable as a material for the reflective layer. In addition, the following may be included. For example, M
g, Se, Hf, V, Nb, Ru, W, Mn, Re, F
e, Co, Rh, Ir, Zn, Cd, Ga, In, S
Metals and metalloids such as i, Ge, Te, Pb, Po, Sn, Bi and the like can be mentioned. Further, those containing Au as a main component are preferable because a reflection layer having high reflectance can be easily obtained. Here, the main component means a component having a content of 50% or more. It is also possible to form a multilayer film by alternately stacking low-refractive-index thin films and high-refractive-index thin films with a material other than a metal, and use it as a reflective layer.

As a method for 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 substance include a thermoplastic resin, a thermosetting resin, an electron beam curable resin, and an ultraviolet curable resin. Further, as the inorganic substance, Si
O ₂ , SiO, Si ₃ N ₄ , MgF ₂ , AlN, SnO _{2 and the} like can be mentioned. A thermoplastic resin, a thermosetting resin, or the like can be formed by dissolving in a suitable solvent, applying a coating solution, and drying. The ultraviolet-curable resin can be formed by applying a coating solution after preparing the coating solution as it is or by dissolving it in an appropriate solvent, and irradiating with ultraviolet rays to cure the resin. As the ultraviolet 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, and may be used not only as a single layer but also as a multilayer film.

As a method for forming the protective layer, a coating method such as a spin coating method or a casting method, a sputtering method or a chemical vapor deposition method is used as in the case of the recording layer, and among them, the spin coating method is preferable.

The thickness of the protective layer is generally 0.1 μm to 1 μm.
In the present invention, the range is from 3 μm to
It is 30 μm, more preferably 5 μm to 20 μm.

A label or the like can be further printed on the protective layer.

Further, a means such as bonding a protective sheet or a substrate to the reflective layer surface, or bonding two optical recording media with the reflective layer surfaces facing each other with the inner surfaces facing each other may be used.

On the mirror surface of the substrate, an ultraviolet curable resin, an inorganic thin film, or the like may be formed to protect the surface or prevent adhesion of dust and the like.

Here, the wavelength of 400 nm to 5
The laser having a wavelength of 00 nm is not particularly limited. For example, a dye laser capable of selecting a wavelength in a wide range of the visible light region, a helium cadmium laser having a wavelength of 445 nm, and a wavelength of 48 nm.
8nm argon laser, wavelength 410nm GaN
And a semiconductor laser that oscillates at 425 to 430 nm, which is the second harmonic of an infrared laser having a wavelength of about 850 to 860 nm. According to the present invention, high-density recording and reproduction can be performed at one wavelength or a plurality of wavelengths selected from these.

[0144]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited by these examples.

Example 1 Among the compounds represented by the general formula (1), 0.2 g of the benzobisoxazole compound (1-1) was dissolved in 10 ml of diacetone alcohol to prepare a compound solution.

Outer diameter 120 m made of polycarbonate resin and having continuous guide grooves (track pitch: 0.7 μm)
This compound solution was spin-coated at 2,000 rpm on a disk-shaped substrate having a thickness of 0.6 mm and a thickness of 0.6 mm, and dried at 70 ° C. for 3 hours to form a recording layer.

Au was sputtered on the recording layer using a sputtering apparatus manufactured by Shimadzu Corporation to form a reflective layer having a thickness of 100 nm. Argon gas was used as a sputtering gas. The sputtering conditions were a sputtering power of 0.5 A and a sputtering gas pressure of 1.0 × 10 ⁻³ torr.

Further, an ultraviolet curable resin S
After spin-coating D-301 (manufactured by Dainippon Ink and Chemicals, Inc.), a substrate without a guide groove similar to the above-mentioned substrate was placed thereon, and the substrates were bonded by irradiating ultraviolet rays to produce an optical recording medium.

The pits were written on the optical recording medium having the recording layer formed as described above as follows.

An optical disk evaluation device (DDU-1000) manufactured by Pulstec Industrial equipped with a 430 nm blue harmonic conversion laser head (NA = 0.65) and KENWO
Using the OD EFM encoder, the shortest pit is 0.
A 4 μm EFM modulated signal was recorded at a linear velocity of 5.6 m / s and a laser power of 10 mW. After recording, a signal was reproduced with the laser output set to 0.5 mW using the same evaluation apparatus. At the time of reproduction, an equalization process was performed.

As a result of measuring the reflectance, the error rate, and the jitter, the reflectance was 50%, the error rate was 7 cps, and the jitter was 9.0%.

Further, the recorded medium was subjected to an accelerated deterioration test (humidity: 85% RH, 100 hours at 80 ° C.), and the reflectance, error rate, and jitter after the test were measured. The change is small, 2% change, 2cps error rate change, 0.5% jitter change,
It was confirmed that it had excellent durability.

Examples 2 to 9 The benzobisoxazole compounds (1-2) to
An optical recording medium was manufactured in the same manner as in Example 1 except that (1-9) was used, and pits were written and recorded, and then signal reproduction was performed. In each case, the reflectance is 40% or more,
The error rate was 11 cps or less, and the jitter was 10% or less.

The change in reflectance after the accelerated deterioration test was 2%.
% Or less, the change in error rate is 2 cps or less, and the change in jitter is as small as 1% or less, confirming that it has excellent durability.

Example 10 Instead of 0.2 g of the compound (1-1) used in Example (1), 0.1 g of the compound (1-28) and the compound (1-28) were used.
33) An optical recording medium was produced in the same manner as in Example 1 except that 0.1 g was used, and pits were written and recorded, and then signal reproduction was performed. As a result, good values were obtained with a reflectance of 47%, an error rate of 9 cps, and a jitter of 9.5%.

The change in reflectance after the accelerated deterioration test was 2%.
%, The change in the error rate was 2 cps, and the change in the jitter was as small as 0.7%. It was confirmed that the device had excellent durability.

Table 2 shows the reflectance, error rate, and jitter before and after the accelerated deterioration test in Examples 1 to 10.

[0158]

[Table 30]

Example 11 Instead of 0.2 g of the compound (1-1) used in Example (1), 0.1 g of the compound (1-10) and 0.1 g of the compound (1-2)
4) An optical recording medium was prepared in the same manner as in Example 1, except that 0.05 g of the compound (1-39) and 0.05 g of the compound (1-39) were used. After recording by writing pits, a signal was reproduced. As a result, the reflectance is 47%, the error rate is 9 cps,
A good value of 9.5% was exhibited.

The change in reflectance after the accelerated deterioration test was 2%.
%, The change in the error rate was 1 cps, and the change in the jitter was as small as 0.6%.

Example 12 Instead of 0.2 g of compound (1-1) used in Example (1), 0.1 g of compound (1-3) and 0.1 g of (1-8) 0.1.
An optical recording medium was prepared in the same manner as in Example 1 except that 1 g was used, and pits were written and recorded, and then signal reproduction was performed. As a result, the reflectance is 45% and the error rate is 10
It showed good values of cps and jitter of 9.7%.

The change in reflectance after the accelerated deterioration test was 2%.
%, The change in error rate was 2 cps, and the change in jitter was as small as 0.8%. It was confirmed that the device had excellent durability.

Examples 13 to 48 Benzobisoxazole compounds (1-10) to
An optical recording medium was prepared in the same manner as in Example 1 except that (1-45) was used, and pits were written and recorded.
The signal was reproduced. As a result, good values were obtained with a reflectance of 40% or more, an error rate of 11 cps or less, and a jitter of 10% or less.

As a result of performing an accelerated deterioration test in the same manner as in Example 1, the change in reflectance from the initial value was 2% or less, the error rate was 2 cps or less, and the jitter was 1% or less.
It was confirmed that it had excellent durability.

Examples 49-56 Benzobisthiazole compounds (1-46)-
An optical recording medium was manufactured in the same manner as in Example 1 except that (1-53) was used, and pits were written and recorded.
The signal was reproduced. In each case, good values were obtained with a reflectance of 40% or more, an error rate of 11 cps or less, and a jitter of 10% or less.

The change in reflectance after the accelerated deterioration test was 2%.
% Or less, the change in error rate is 2 cps or less, and the change in jitter is as small as 1% or less, confirming that it has excellent durability.

Example 57 In place of 0.2 g of the compound (1-1) used in Example (1), 0.1 g of the compound (1-28) and the compound (1-28) were used.
46) An optical recording medium was prepared in the same manner as in Example 1 except that 0.1 g was used, and pits were written and recorded, and then signal reproduction was performed. As a result, good values were obtained with a reflectance of 47%, an error rate of 8 cps, and a jitter of 9.4%.

The change in reflectance after the accelerated deterioration test was 1
%, The change in error rate was as small as 2 cps, and the change in jitter was as small as 0.4%, confirming excellent durability.

Example 58 Instead of 0.2 g of compound (1-1) used in Example (1), 0.1 g of compound (1-79) and 0.1 g of compound (1-
88) An optical recording medium was prepared in the same manner as in Example 1 except that 0.1 g was used, and pits were written and recorded, and then signal reproduction was performed. As a result, good values were obtained with a reflectance of 47%, an error rate of 9 cps, and a jitter of 9.4%.

The change in reflectance after the accelerated deterioration test was 2%.
%, The change in the error rate was 2 cps, and the change in the jitter was as small as 0.7%. It was confirmed that the device had excellent durability.

Table 3 shows the reflectance, error rate, and jitter before and after the accelerated deterioration test in Examples 49 to 58.

[0172]

[Table 31]

Examples 59 to 96 Benzobisthiazole compounds (1-54) to
An optical recording medium was prepared in the same manner as in Example 1 except that (1-91) was used, and pits were written and recorded.
The signal was reproduced. In each case, good values were obtained with a reflectance of 40% or more, an error rate of 11 cps or less, and a jitter of 10% or less.

The change in reflectance after the accelerated deterioration test was 2%.
% Or less, the change in error rate is 2 cps or less, and the change in jitter is as small as 1% or less, confirming that it has excellent durability.

Examples 97 to 127 Benzoxathiazole compounds (1-92) to
An optical recording medium was manufactured in the same manner as in Example 1 except that (1-122) was used, and pits were written and recorded, and then signal reproduction was performed. In each case, the reflectance is 40%
As described above, the error rate was 11 cps or less, and the jitter was 10% or less, which were good values.

The change in reflectance after the accelerated deterioration test was 2%.
% Or less, the change in error rate is 2 cps or less, and the change in jitter is as small as 1% or less, confirming that it has excellent durability.

Example 128 Optical recording was performed in the same manner as in Example 1 except that 0.2 g of the compound (1-123) was used instead of 0.2 g of the compound (1-1) used in the example (1). After a medium was prepared and pits were written and recorded, signal reproduction was performed. as a result,
8. Reflectivity 45%, error rate 10 cps, jitter 9.
A good value of 7% was shown.

The change in reflectance after the accelerated deterioration test was 2%.
%, The change in the error rate was 1 cps, and the change in the jitter was as small as 0.6%.

Examples 129 to 137 Benzoxathiazole compound (1-124) was added to the recording layer.
An optical recording medium was manufactured in the same manner as in Example 1 except that (1-132) was used, pits were written and recorded, and then signal reproduction was performed. In each case, the reflectance is 40%
As described above, the error rate was 11 cps or less, and the jitter was 10% or less, which were good values.

The change in reflectance after the accelerated deterioration test was 2%.
% Or less, the change in error rate is 2 cps or less, and the change in jitter is as small as 1% or less, confirming that it has excellent durability.

Table 4 shows the reflectance, error rate, and jitter before and after the accelerated deterioration test in Examples 128 to 137.

[0182]

[Table 32]

As described in Examples 1 to 137, all of the optical recording media of the present invention have high reflectivity and are excellent in recording characteristics and durability.

From this, the recording layer containing the benzobisoxa / thiazole compound having the structure defined in the present invention can record a signal with a blue laser, and the optical recording medium of the present invention uses the blue laser for recording and reproduction. It can be used for an optical recording medium to be used.

Comparative Example 1 Instead of the compound (1-1), a compound of the formula (a)

[0186]

Embedded image An optical recording medium was manufactured and pits were written in the same manner as in Example 1, except that pit was used, and then an accelerated deterioration test was performed. As a result, it was found that the recording layer was discolored and became unreproducible, and this medium lacked storage stability.

Comparative Example 2 Instead of the compound (1-1), a compound of the formula (b)

[0188]

Embedded image An optical recording medium was produced in the same manner as in Example 1 except that を was used. Crystal precipitation was observed in the recording layer of this medium, pits could not be written, recording was impossible, and reproduction was impossible.

[0189]

According to the present invention, by using the compound represented by the general formula (1) as a recording layer, the wavelength of 400 nm to 5 nm, which is attracting much attention as a high-density optical recording medium, is obtained.
It is possible to provide a write-once optical recording medium that can record and reproduce with a 00 nm laser.

[Brief description of the drawings]

FIG. 1 is a sectional structural view showing an example of a layer configuration of an optical recording medium according to the present invention.

FIG. 2 is a sectional structural view showing an example of a layer configuration of an optical recording medium according to the present invention.

[Explanation of symbols]

 1: substrate 2: recording layer 3: reflective layer 4: protective layer 5: adhesive layer

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Tsukahara U 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Inside (72) Inventor Taizo Nishimoto 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Mitsui Chemical Co., Ltd. 72) Inventor Densumi Misawa 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Inside of Mitsui Chemicals Co., Ltd. EA22 EA32 EA40 EA48 FA01 FA12 FB42 4H056 CA02 CA05 CB05 CB06 CC05 CD05 CE03 CE07 DD19 DD23 EA16 FA05 5D029 JA04 JC17

Claims (2)

[Claims] 1. An optical recording medium having at least a recording layer and a reflective layer on a substrate, wherein the recording layer has the general formula (1)
An optical recording medium containing a benzobisoxa / thiazole compound represented by the formula: Embedded image [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R ⁸ each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, an aralkyl Group, aryl group, alkoxy group, aralkyloxy group, aryloxy group, alkenyl group, alkenyloxy group, alkylthio group, aralkylthio group, arylthio group, alkylamino group, aralkylamino group, arylamino group, alkenylamino group, acyl Group, alkoxycarbonyl group,
An aralkyloxycarbonyl group, an aryloxycarbonyl group, an alkenyloxycarbonyl group, an alkylaminocarbonyl group, represents a heterocyclic group, and ring A and ring B each independently represent an oxazole ring or a thiazole ring;
Z ¹ , Z ² , Z ³ and Z ⁴ each independently represent a substituted or unsubstituted alkyl group, aralkyl group, alkenyl group or aryl group. Alternatively, Z ¹ and Z ² and Z ³ and Z ⁴ may be linked to each other to form a ring. ] 2. The optical recording medium according to claim 1, wherein recording and reproduction can be performed with respect to a laser beam selected from a wavelength range of 400 nm to 500 nm.