JPH02568A - Optical recording medium - Google Patents

Abstract

PURPOSE:To obtain an optical recording medium having high solubility in organic solvent, sufficient coating properties, high reflectivity, sufficient contrast and excellent retentivity by employing specific metal-containing indoaniline compound as dye. CONSTITUTION:Metal-containing indoaniline compound represented by a formula is employed as dye. In the formula, the M is metal atoms of group VIII elements, group Ib-IIIb elements, and group IVa-VIIa elements, their halogenides and oxides, which may contain substituted group of rings A-I. The R<1>-R<6> are hydrogen atom, alkyl group, aryl group, alkenyl group, cycloalkyl group which may be substituted. However, at least one of the R<1> and R<2>, R<3> and R<4>, R<5> and R<6> is alkyl group which is substituted. The Q is anionic ion (except PF6<->), the l, m, n are 0 or 1, wherein (l+m+n) are 2 or 3.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an optical recording medium using a metal-containing indoaniline compound.

[Conventional technology]

Optical recording using lasers has been particularly developed in recent years because it enables high-density information storage, storage, and reproduction.

An example of an optical recording medium is an optical disc.

In general, optical discs record high-density information by irradiating a thin recording layer provided on a circular base with laser light focused on the order of /μm. The recording is performed by thermal deformation such as decomposition, evaporation, melting, etc. occurring in the recording layer at that location due to absorption of irradiated laser light energy. Further, the recorded information is reproduced by reading the difference in reflectance between a portion where deformation has occurred and a portion where deformation has not occurred by means of a laser beam.

Therefore, as an optical recording medium, it is necessary to efficiently absorb the energy of laser light, so the absorption of laser light of a specific wavelength used for recording is large, and in order to accurately reproduce information, it is necessary to efficiently absorb the energy of laser light. It is necessary that the reflectance for laser light of a specific wavelength is high.

Various types of optical recording media are known.

For example, Japanese Unexamined Patent Publication No. 5-27033 discloses a device in which a single layer of a phthalocyanine dye is provided on a substrate. However, phthalocyanine dyes have problems such as low sensitivity, high decomposition point, and difficulty in vapor deposition.Furthermore, they have extremely low solubility in organic solvents, making them unsuitable for use in coatings. ing.

Further, JP-A-6L-43311U discloses a recording layer in which a phenalene dye is provided, and JP-A-JJ'-22F773 discloses a recording layer in which a naphthoquinone dye is provided. However, although such dyes have the advantage of being easy to deposit, they have the problem of low reflectance. If the reflectance is low, the contrast related to the reflectance between the portion recorded by the laser beam and the unrecorded portion will be low, making it difficult to reproduce the recorded information. Furthermore, organic dyes generally have a problem of poor storage stability.

[Problem to be solved by the invention]

The present invention provides an optical recording medium using a metal-containing indoaniline compound that has high solubility in organic solvents, can be coated by coating, has high reflectance, good contrast, and has excellent storage stability. The purpose is to

[Means to solve the problem]

The present invention involves irradiating a recording layer containing a dye supported on a substrate with a focused laser beam that thermally changes the dye.
Performing recording by causing a partial change in the recording layer,
The gist of the present invention is an optical recording medium in which reproduction is performed by selecting the changed portion, in which a metal-containing indoaniline compound represented by the following general formula [I] is used as the dye.

represents a loalkyl group, where R1 and R2, R3 and R
4. At least one of R5 and R6 represents a substituted alkyl group. Q represents an anion (excluding PF6-), and L, m, and n are each O or /.

However, t+m+n Vi represents 2 or 3. ) Preferred metal-containing indoaniline compounds used in the optical recording medium of the present invention include those represented by the following general formula.

(In the formula, M represents a subgenus atom of Group I, Group Ib, Group IIb, Group Ib, Group ■a, Va group, Va group, Va group, their halides, and their oxides, and ring A, B% C, D%E%F
, G, H, ■ may have a substituent. R1,
R2, R3, R4, R5, and R6 are a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkenyl group, an optionally substituted Schiff I R2 - 1-h (wherein M is group ■, group 1b, group ■b, [group Ib, lVa
Represents metal atoms of the Va group, Va group, Va group, their halides, and their oxides.

R7, R8, R9, RIG, R11, RI2, XI,
X2, X3, yl.

Y2 and Y3 are hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, acylamino groups, acyloxyamino groups,
Represents an alkoxycarbonylamino group or an alkylsulfonylamino group, R1, R2゜R3, R4, R5, R6
represents a hydrogen atom, an optionally substituted C8-2o alkyl group, an optionally substituted aryl group, an optionally substituted alkenyl group, an optionally substituted cycloalkyl group; R1 and R2, R3 and R4,
At least one of R5 and R6 represents a substituted alkyl group. Q represents an anion (excluding PF6-),
L, m, rl are each O or l, but t+m
+n represents Viλ or 3. ) Preferably, the metal atom represented by M in the general formulas [1] and (n) is N1, Zn, Cu(1), Cu(11), C
o, Fe (1), Fe (■), Pd, At,'
ri, Pt (■), pt (IV), V, C3r,
Mn, In (l[l), Ru (Ill),
Examples include Sn (If), and examples of its oxides and halides include vo, Atct, and the like.

Furthermore, in general formula (1), rings A, B, (3, D,
As substituents for K, F, G, H1■, the general formula (I
I) R1, R8, R9, RIG, R11, RI2
, XI, x2, X3, yl, y2, and Y3, preferably lower alkyl groups, lower alkoxy groups, lower acylamino groups, halogen atoms, and lower alkoxycarbonylamino groups.

Examples of the alkyl groups represented by R1, R2, R3, R4, R5, and R6 include alkyl groups having -20 carbon atoms.

Examples of this substituent include an alkoxy group, an aryl group, a hydroxy group, a cyano group, a tetrahydrofuryl group, an alkoxyalkoxy group, an aryloxy group, an alkenyloxy group, an alkylsulfonylamino group, an acyloxy group, a tetrahydrofurfuryloxy group, and an alkoxyalkoxy group. Examples include alkoxy groups.

Examples of the aryl group include phenyl group and tolyl group,
Examples of the alkenyl group include vinyl group, allyl group, (n-) or (1so-)globenyl group, (ieo-)butenyl group, and these alkenyl groups and aryl groups include lower alkyl groups and lower alkoxy groups. group, halogen atom, nido.

may be substituted with a group, a cyano group, or a hydroxy group.

'7 cycloalkyl group is cyclohex'/)L'M,
Examples include cyclopentyl groups, and these groups may be substituted with lower alkyl groups.

More preferred examples of the metal-containing indo-aniline compound used in the present invention include those represented by the following general formula (Ill).

[In the formula, M is N1, Cu, C01Zn or Fe (11
) represents a metal atom, R13 and RI4 represent a hydrogen atom, a halogen atom or a lower alkyl group, X and Y represent a hydrogen atom, a lower alkyl group, a halogen atom such as Br%F%Ct, C2-8 (benzoylamine, ) group, acylamino group (including benzylcarbonylamino group), lower alkoxy group of 01-4 or C8~, acyloxyamino group (including benzoyloki7-amino group, benzylcarbonyloxyamino group), R15, R” Vic, ~
, lower alkyl group; C3-4 lower alkoxy group, 0
3-6 alkoxyalkoxy group, 05-8 alkoxyalkoxyalkoxy group, aryl group such as allyloxy group, phenyl group, tolyl group, aryloxy group such as phenyloxy group, tolyloxy group, cyano group, hydroxy group, tetrahydrofuryl group, a tetrahydrofurfuryloxy group, a C2-4 alkylsulfonylamino group or a C8-4 lower alkoxy group substituted by a CI-8 acyloxy group (including benzoyloxy group and benzylcarbonyloxy group), a halogen atom, C optionally substituted with a nitro group, cyano group, or hydroxy group
represents an alkenyl group of 2 to 8, with the proviso that RISRIM
At least one of them represents a substituted alkyl group. 2
represents an anion (excluding PF6″), m and n are /
Or represents the number 2. However, when m is l, n represents ko, and when m is 1, n represents /. ] Particularly preferred are those represented by the following general formula (IV).

Hydrogen atom, lower alkyl group of 01-4, Br, F,
Halogen atoms such as C1, acyloxyamino groups of 01 to 8 (including benzoylamino groups and benzylcarbonylamino groups), and benzylcarbonyloxyamino groups)
represents an acyloxyamino group, RIS, R16
is a C8-4 lower alkyl group; a C8-4 alkoxy group, a C3-6 alkoxyalkoxy group, a C5-8 alkoxyalkoxyalkoxy group, a (in the formula, M is N1
, Cu, Co, Zn, Fe (■) represents a metal atom, and RI3 and RI4 are hydrogen atoms, hydrogen atoms, or C,
-4 represents a lower alkyl group, X and Y represent an aryloxy group, a cyan group, a hydroxy group, a tetrahydrofuryl group, a tetrahydrofurfuryloxy group, an alkylsulfonylamino group of CI-4 or a benzoyloxy group of 01-8 , a lower alkyl group of CI~4 substituted with an acyloxy group (including a benzylcarbonyloxy group); represents an optionally substituted C2-8 alkenyl group, provided that at least one of RIS and RIIS represents a substituted alkyl group. 2 represents an anion (excluding PF6-), m and n represent/or the number of λ. However, when m is l, n represents λ, and when m is 2, n represents l
represents. ] Examples of anions represented by Q and 2 include I, Br, C1, F, (104, B
F4, SON.

5OINH2, SbF'6, ZrF62CI3 R35
0□, TiF6C3-Co.

, CN-,C,,,H33COO”-1B(○)4-
Examples include monovalent or divalent anions such as 1, preferably I, Br, C! 1-1c1o;, BF", 5
It is an anion of bvi.

General synthesis of metal-containing indoaniline compounds is described, for example, by Yuji Kubo, Masako Sasaki, Kappei Yoshida;
It can be conducted in accordance with the description in 3rd Autumn Annual Conference Lecture Proceedings/RIR, 63RI. That is, the following general formula [■] (in the formula, RI3 and RI4 are the same as defined above) is added to the compound represented by the general formula (V) , X, Y, R15
, R16 are the same as defined above. ) to obtain the general formula J [■] R13, R14 (wherein R13, R14, R15, R16, X, and Y are the same as defined above). Next, the above compound and the following general formula [■] u
(z)n ・・・・・・・・・・・・〔■〕
(wherein M, Z, , m and n are the same as defined above).

The optical recording medium of the present invention is basically composed of a substrate and a recording layer containing a metal-containing paulownia indoaniline compound, but if necessary, an undercoat layer and a recording layer may be added on the substrate. A protective layer can be provided on top.

The substrate in the present invention may be either transparent or opaque to the laser beam used. Examples of the substrate material include supports for general recording materials such as glass, plastic, paper, plate-shaped or foil-shaped metal, etc.
Plastic is preferred for various reasons. Examples of the plastic include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, epoxy resin, polysulfone resin, and the like.

Among these, injection molded polycarbonate resin substrates are particularly preferred in terms of high productivity, cost, and moisture absorption resistance.

The recording layer containing the metal-containing indoaniline compound in the optical recording medium of the present invention has a film thickness/00 A=j μ
m, preferably 1OOOA to 3 μm. The film can be formed by a commonly used thin film forming method such as a vacuum evaporation method, a sputtering method, a doctor blade method, a casting method, a spinner method, or a dipping method.

Moreover, a binder can also be used if necessary. The binder is PVA%PVP.

Known materials such as nitrocellulose, cellulose acetate, folivinyl butyral, and polycarbonate are used, and the weight ratio of the metal-containing indoaniline compound to the resin is preferably 0.5071 or more. In the case of film formation by a spinner method, the rotational speed is preferably 1005-jooorprn, and after the spin code, treatment such as heating or exposure to solvent vapor may be performed as the case requires.

In addition, to improve the stability and light resistance of the recording material, transition metal chelate compounds (e.g., acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α) are used as heavyt oxygen quenchers.
- diketone, etc.).

The metal-containing indoaniline compound used in the optical recording medium of the present invention may be used alone, or a mixture of two or more types having different substituents or two or more types having different coordination numbers; A mixture of dyes obtained as a result of manufacturing may be used, and further, other dyes may be used in combination as necessary. The other dyes may be other types of compounds of the same type, or dyes of other types such as triarylmethane dyes, azo dyes, cyanine dyes, squarylium dyes, etc.

When forming a recording layer by a coating method such as a doctor blade method, a casting method, a spinner method, or a dipping method, in particular, a spinner method, the coating solvents include tetrachloroethane, bromoform, dibromoethane, diacetone alcohol, ethyl cellosolve, and xylene. , 3-hydroxy-3-methyl-2-butanone, chlorobenzene, cyclohexanone and the like having a boiling point of 720 to 60°C are preferably used.

Among these, cellosolve-based solvents such as methyl cellosolve and ethyl cellosolve are particularly suitable for injection-molded polycarbonate resin substrates, which have excellent productivity, cost, and moisture absorption resistance, and can be used without destroying the substrate. ; diacetone alcohol, 3-hydroxy-3-)f
Examples include ketone alcohol solvents such as 2-butanone.

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

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

The recorded information is reproduced by using laser light to read the difference in reflectance between areas where thermal deformation has occurred and areas where thermal deformation has not occurred.

The laser light used for the optical recording medium of the present invention is N2, Ha-C! d, Ar, He-N3. Examples include ruby semiconductors and dye lasers, but semiconductor lasers are particularly preferred in terms of lightness, ease of handling, and compactness.

〔Example〕

EXAMPLES The present invention will be specifically explained below with reference to Examples, but these Examples are not intended to limit the present invention.

Example 1 (a) Production example Compound represented by the following structural formula /, 0? r to evening 00. N1(C104)2・AH2 dissolved in 1 liter of ethanol
A solution of 02,12F in 00 ml of water was added at room temperature over about 1 hour, and the mixture was stirred at room temperature for an hour.

Thereafter, the mixture was left to stand overnight and stirred for λ hours under water cooling. Next, the obtained precipitate is suction filtered, washed with water and dried to form a metal-containing indoaniline compound represented by the following structural formula /, 3 J ?
(Yield: 0%) was obtained.

Visible absorption spectrum of this compound (in chloroform)
As shown in Figure 7, λmax 7tata nm (tmax
/23000).

b) Recording medium example The metal-containing indoaniline compound obtained in the above production example (a). /! ;? 3-hydroxy-3-methyl-2-
Butanone 10? and filtered through a 0.22μ filter to obtain a solution. This melting! mA! depth 70
It was dropped onto an injection molded polycarbonate resin substrate (5 inches) with grooves (groups) having a width of 0.7 μm and was coated using a spinner method at a rotation speed of j 00 rpm.

After coating, it was dried at 60°C for 70 minutes. The maximum absorption wavelength of the coating film is 7 nm, and the reflectance is ≠θ% (r J
Onm). The shape of the spectrum was wide.

Figure λ shows the absorption and reflection spectra of the coating film.

(C) Optical recording method While rotating the above recording medium at ≠m7 days,
' Norx width j 0 with 30 nm semiconductor laser light
When irradiated at 0 n5ec, the output was mW and the a/N
The ratio j J-dB was obtained. Storage stability (xr℃, to%R
H) was also good and was extremely excellent as an optical recording medium.

Example λ (a) Production example A compound represented by the following structural formula /, / J r was dissolved in 74-0.1 ethanol, and an aqueous solution of N1(BF4)2 was added to /, 0 tf. The mixture was added and stirred at room temperature for about 1 hour. Then, the solvent was distilled off under reduced pressure and the mixture was dried. Next, xomg of ethanol and 10 ml of water were added to form a precipitate, which was then stirred in a suspended state for about 1 hour. The obtained precipitate was suction filtered, washed with water, and dried to obtain a metal-containing indoaniline compound represented by the following structural formula, 022 (overall yield: 7j%).

Visible absorption spectrum of this compound (in chloroform)
is λmaxJ'00nm (εma
x/2λooo).

(1)) Recording medium example The metal-containing indoaniline compound θ, /j obtained in the above production example (a) was dissolved in 10f of diacetone alcohol,
．． The solution was filtered through a 22μ filter to obtain a solution. Five drops of this solution were dropped onto an injection molded polycarbonate resin substrate (tinch) with grooves (groups) 700 mm deep and 0.7 μ wide, and coated using a spinner at a rotation speed of 200 rpm. After coating, it was dried at 60°C for 70 minutes. The maximum absorption wavelength of the coating film is f03 nm, and the reflectance is tAO% (
130nrn). The shape of the spectrum was wide.

Figure ≠ shows the absorption and reflection spectra of the coating film.

(C) Optical recording method While rotating the above recording medium at ≠m/θ, the central wavelength 1
With a 30 nm semiconductor laser beam, the laser beam width is 00
When irradiated with n5ec, a c/N ratio j 3 dB was obtained with an output of 9 mW. Storage stability (Gj℃, to%RH
) was also good, making it an extremely excellent optical recording medium.

Example 3 (a) Preparation Example The following structural formula was stirred for a period of time. Thereafter, the mixture was left to stand overnight, and then stirred for 2 hours under water cooling. The resulting precipitate was then suction filtered, washed with water, and dried to obtain a mixture of metal-containing indoaniline compounds 7.2≠2 represented by the following structural formula.

N1(a1o4)2・AH2 was added to a solution of the compound o3r r represented by
02J 2 f was dissolved in water roOrttl and Shitamono was added at room temperature for about 1 hour. At room temperature, the visible absorption spectrum (in chloroform) of the three products was λma
It was nm.

(b) Recording medium example A mixture of the metal-containing indoaniline compounds obtained in the above production example (a). /j? diacetone alcohol 10?
The solution was dissolved in water and filtered through a 052λμ filter to obtain a solution. This solution j tnl was dropped onto an injection molded polycarbonate resin substrate (5 inches) with grooves (groups) of depth 700^ and width 0.7μ, and spun at 700 rpm using a spinner method.
The coating was performed at a rotational speed of m. After coating, it was dried at 60°C for 10 minutes. The maximum absorption wavelength of the coating film is r 00 nm,
The reflectance was pO% (rJOnm). The shape of the spectrum was broader than with one compound.

(CI Optical Recording Method While rotating the above recording medium at ≠ m/s, pulse width with a semiconductor laser beam with a center wavelength of 130 nm! 00
When irradiated at nsθC, a C/N ratio j @ dB was obtained with an output of 9 mW. Storage stability (gt℃, go%RH
) was also good, making it an extremely excellent optical recording medium.

Example ≠ When a solution obtained by using the compounds shown in Table 1 instead of the compounds used in Example/ was applied onto a substrate, an optical record having the maximum absorption wavelength of the coated film shown in Table 1 was obtained. Got the medium. When writing was performed on the recording medium thus obtained using a semiconductor laser as a light source,
The c/N ratio was good and pits with a uniform and clear shape were obtained, and the storage stability was also good.

In addition to the compounds used in the above Examples, Table 2 shows specific examples of metal-containing indoor dihydrogen compounds that are preferably used in the optical recording medium of the present invention.

Example! A compound represented by the following structural formula/,/41'? was dissolved in Tatami ethanol 5oo7, N1(czo4)2
A solution of ゜Otsu H200,37F in water j 00 Ql was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for about 2 hours.

The obtained precipitate was suction filtered, washed with water, and dried to obtain a metal-containing indoaniline compound represented by the following structural formula.

The visible absorption spectrum (in aoform) of this compound is λmax 7nm (εmax / 6000
0).

(1)) Recording medium example The metal-containing indoaniline compound o, trt obtained in Production Example (a) was dissolved in 3-hydroxy-3-methyl-2-butanone lO2 and filtered with a 0.2λμ filter. ,
A solution was obtained. This solution! me to depth 700A, width 0
．． It was dropped onto an injection molded polycarbonate resin substrate (5 inches) with 7μ grooves (groups) and
Coating was carried out at a rotation speed of 0.00 rpm. 1 at 10℃ after application
After drying for 0 minutes, the maximum absorption wavelength of the fC6 coating film is 7 tat nm.
The reflectance was vO% (130 nm). The shape of the spectrum was wide.

(C) Optical recording method While rotating the above recording medium at ψm/8, record the pulse width using a semiconductor laser beam with a center wavelength of 710 nm. 00
When irradiated with n5ec, the output cuff was c/N at mW.
The ratio j j dB was obtained. Storage stability (6!℃, go%
RH) was also good and was excellent as an optical recording medium.

Example t (a) Manufacturing example In Example j, N 1 (C104)z JH200
,37f (7) Zn(C!tO4)2 ・AH instead
A metal-containing indoaniline compound represented by the following structural formula was obtained in the same manner as in Example j except that 200,j J' f was used.

Visible absorption spectrum of this compound (in chloroform)
was λmax 7 j nm.

(b) Recording medium example-l 0.72% of the metal-containing indoaniline compound obtained in the above production example (a) was dissolved in 109% of tetrachloroethane, and 0.2%
The solution was filtered through a λμ filter to obtain a solution. This solution j
Tug depth 7 o o x.

The mixture was dropped onto a PMMA resin substrate (5 inches) with grooves (groups) made of ultraviolet curable resin having a width of 0.7 μm, and coated using a spinner method at a rotation speed of 00 rpm. After application, t
It was dried at 0° C. for 70 minutes.

(C) Optical recording method-1 While rotating the j-inch PMMA resin substrate on which the above recording medium was deposited at um/θ, the central wavelength was 7 r Onm.
When irradiated with a semiconductor laser beam with a pulse width of j 00 n8ec, the c / N ratio j 2 d at an output of t mW
I got a B. Storage stability (A (7°C, 10% RH)) was also good.

(a) Recording Medium Example-1 The metal-containing indoaniline compound obtained in Production Example (a) 0. / 7 f to ethyl cellosolve 10? dissolves in 0
．． The solution was filtered through a 2λμ filter to obtain a solution. J ml of this solution was dropped onto a polycarbonate resin substrate (injection molded product, 5 inches) with grooves (groups) with a board thickness of /, 21101 and /j μm pitch, and J' 0 was added using a spinner method.
Coating was carried out at a rotation speed of 0 rpm. After application, 70℃ at 6o℃
Dry for a minute.

(e) Optical recording method-2 5-inch polycarbonate coated with the above recording medium) 1
While rotating the 11 fat substrate at ≠m/e, the center wavelength is 7r.
Pulse width J 00 n days e with semiconductor laser light of θnm
When irradiated with c, the output A mW and the C/N ratio! ; O
I got dB. Storage stability (60°C, go%RH) was also good.

Example 7 (a) Manufacturing Example In Example j, N1(C1O4)2・JH200,
C0(C104)2・AH200,37 instead of 37f
A metal-containing indoaniline compound represented by the following structural formula was obtained in the same manner as in Example except that F was used.

Visible absorption spectrum of this compound (in chloroform)
was λmax 7 tat nm.

(b) Example of recording medium An example of the metal-containing indoaniline compound obtained in Production Example (a) above! Coating was performed on a PMMA resin substrate with grooves (groups) using a spinner method according to the method described in . The maximum absorption wavelength of the coating film was 7.7 nm, and the shape of the spectrum was wide.

(c) Optical recording method While rotating the above PMMA resin substrate at Fm/s,
When irradiated with a semiconductor laser light beam with a center wavelength of 7 r Onm and a pulse width of j 00 n5ec, the output A m
C/N ratio with W! Obtained OdB.

Storage stability (10°C, 10°C RH) was also good.

Example t (a) Production Example A compound represented by the following structural formula: FP/300. N1(cto4)2・AH20o3 dissolved in 1 liter of ethanol
A solution of 100ml of water was added to the mixture, and the mixture was stirred at room temperature for 2 hours.

The obtained precipitate is suction filtered, washed with water, and dried to obtain a mixture O of metal-containing indoaniline compounds represented by the following structural formula.
I got 6 years of experience.

(b) Recording medium example A mixture of the metal-containing indoaniline compounds obtained in Production Example (a) above. / j P as diacetone alcohol 702
The solution was dissolved in water and filtered through a 0.22μ filter to obtain a solution. This solution was dropped onto an injection molded polycarbonate resin substrate (5 inches) with grooves (groups) having a depth of 70 OA and a width of 0.7 μm, and was applied using a spinner method at a rotation speed of SOO rpm. After coating, it was dried at to°C for 70 minutes.

The maximum absorption wavelength of the coating film is lθθnm, and the reflectance is 4
to% (130 nm). The shape of the spectrum was broader than with one compound.

(C) Optical recording method While rotating the above recording medium at Vm/s,
r Onm semiconductor laser light with pulse width j 00
When irradiated at nsθC, the output cuff was c/N at mW.
The ratio j F dB was obtained. Storage stability (xj'c, zaO%
RH) was also good.

When a solution obtained by using the compounds shown in Table 3 instead of the compounds used in Example j was applied onto a substrate, an optical record with the maximum absorption wavelength of the coated film shown in Table 3 was obtained. Got the medium. When writing was performed on the recording medium thus obtained using a semiconductor laser as a light source,
The C/N ratio was good, and a uniform and clear focus was obtained, and the storage stability was also good.

In addition to the compounds used in the above Examples, specific examples of metal-containing indoor di-IJ compounds suitable for use in the optical recording medium of the present invention are shown in Tables 1 and 1 below.

Table 5 shows specific examples of compounds used in the optical recording medium of the present invention, including M, R', R2, and R in the general formula below.
3, R4, R5, R6, and Q.

℃−111ノ≠ [Effects of the Invention] The metal-containing indoaniline compound of the present invention has high solubility in organic solvents, can be coated by coating, and has high reflectance and good contrast. Since this compound has excellent storage stability, optical recording media using this compound are extremely useful.

[Brief explanation of the drawing]

Figures 1 and 3 show the absorption spectra in the visible region of the metal-containing indoaniline compound λ example (Example/and Example λ) of the present invention, where the vertical axis is the absorbance and the horizontal axis is the wavelength. (nm). Figure-1 and Figure-≠ represent the absorption spectrum and reflection spectrum of the coated thin film (Example/and Example 2) of the metal-containing indoaniline compound λ example of the present invention, and the left axis of the vertical axis represents the absorbance. , the right side represents the reflectance, and the horizontal axis represents the wavelength (nm
). Low 2 Sodaiou) Namisen 61m) Figure 3

Claims (1)

[Claims] (1) Recording is performed by irradiating a recording layer containing a dye supported on a substrate with a focused laser beam that causes a thermal change in the dye to cause a partial change in the recording layer, and then performing the recording. An optical recording medium in which reproduction is performed by selecting a portion, characterized in that a metal-containing indoaniline compound represented by the following general formula [I] is used as the dye. ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, M is group VIII, group Ib, group IIb, group IIIb, IVa
Represents metal atoms of group Va, group VIa, group VIIa, their halides and their oxides, and rings A, B, C, D, E
, F, G, H, and I may have a substituent. R^1
, R^2, R^3, R^4, R^5, R^6 are hydrogen atoms, optionally substituted alkyl groups, optionally substituted aryl groups, optionally substituted alkenyl groups ,
Represents an optionally substituted cycloalkyl group, provided that R^1 and R^2, R^3 and R^4, R^5 and R^6
At least one of them represents a substituted alkyl group. Q
represents an anion (excluding PF_6^-), l, m,
n represents 0 or 1, but l+m+n represents 2 or 3, respectively. )