JP2501005B2 - Optical recording medium and recording film material thereof - Google Patents

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 on / from which information can be written / read by a laser beam. More specifically, it relates to a recording film structure of a write-once compact disc and a recording film material thereof.

[0002]

2. Description of the Related Art Among information recording media using a condensed laser beam, a compact disk (CD) for reproducing music such as audio has become widespread. In such a CD, a pit row having a CD format signal is usually formed on the surface of a transparent substrate such as polycarbonate at the time of injection molding, and aluminum or gold is provided as a reflection film by vapor deposition or sputtering, and a protective layer is further coated. To create. Reproducing laser light (780 nm semiconductor laser light) is irradiated from the back surface of the substrate of the optical disk thus created, each signal is read from the change in reflectance due to the unevenness of the pits, and information is reproduced. However, since such a CD is read-only and cannot be recorded, there is an inconvenience that it does not have an editing function such as a write-once optical disc or a rewritable magneto-optical disc. On the other hand, as a write-once optical disk or magneto-optical disk having an editing function, a recording film made of a chalcogenite compound such as Te, a rare earth metal compound or an organic dye such as cyanine or naphthalocyanine has been put into practical use. However, these optical discs have a low reflectance from the substrate surface, and as they are, CDs or CD-ROs are used.
There is a problem that the signal cannot be reproduced by the reproducing apparatus of M. In order to solve such a problem, a reflective film such as gold is provided on the recording film such as cyanine,
CD of 780 nm with a surface reflectance of 70% or more
An optical disk and a method for recording a format or CD-ROM format signal and reading information by a CD or CD-ROM reproducing device have been proposed.

However, since cyanine dyes generally have poor photostability, there is a possibility that the reliability of recording may be deteriorated under a use condition such as CD in which a single-sided structure is directly exposed to sunlight. Therefore, attempts are being made to use a phthalocyanine dye, which has excellent chemical and physical stability, as a recording film material instead of the cyanine dye.

As such a phthalocyanine dye,
The recording film material proposed in JP-B-4-53713 is effective, but the phthalocyanine dyes shown here are
The characteristics peculiar to conventional phthalocyanine compounds have not been sufficiently improved, and the recording sensitivity is low because it is very stable thermally,
Further, since the absorption band is very sharp, it is difficult to obtain stable optical characteristics (reflectance and absorption) in the permissible range (about 770 to 810 nm) of the oscillation wavelength of the semiconductor laser mounted in the pickup of the CD drive. However, there are still problems such as large wavelength dependence of recording sensitivity, and it is not always a material having sufficient characteristics as a recording film material for a write-once compact disc.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides an inexpensive specific phthalocyanine compound which is chemically and physically stable and can be recorded and reproduced with high sensitivity by a laser beam, and an optical recording medium using the same. With regard to the CD type optical recording medium, the drawbacks of the conventional CD or CD-ROM having the write-once function and the edit function are solved, and 770
The present invention provides a red book-compliant optical disc that realizes stable optical characteristics in the wavelength range of nm to 810 nm and is capable of complete recording and reproduction in this wavelength range.

[0006]

[Means for Solving the Problems]
As a result of a more detailed examination of the phthalocyanine-based optical recording material proposed in JP-53713-A, an organic thin film containing a specific phthalocyanine compound is formed into an optical film composed of a substrate / recording film / reflection film / protective film laminate. By applying it to a recording film of a recording medium, they have found to have various excellent characteristics, and have completed the present invention. That is, the present invention is a phthalocyanine compound-based recording film material represented by the general formula [I] and applicable to a recording film of an optical recording medium composed of a laminated body of a transparent substrate / recording film / reflection film / protective film, and the same. Is an optical recording medium using. General formula [I]

Embedded image [In the formula, the substituent X represents a 2,2-bis (trifluoromethyl) propoxy group. The substituents Y ^{1 to} Y ⁴ are each independently a halogen atom, an alkyl group which may have a substituent,
An aryl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, and a substituent also good arylthio group, a nitro group, a cyano group, a sulfonic acid group, a sulfonic acid amide group, a sulfonic acid ester group, n1 to n4 represents an integer of 0 to 3 in the number of substituents Y ¹ to Y ^4. The central metal M represents Si or Al. The substituent ^{Z, -OP (= O) R 1} R 2 or -OP (= O)
Represents Ar ¹ Ar ² . However, R ¹ and R ² represent a linear, branched or cyclic alkyl group which may have a substituent, and A 1
r ¹ and Ar ² represent an aryl group which may have a substituent.
m represents the number of substituents Z and is an integer of 1 or 2. ]

The above-mentioned problems have been solved by forming the recording film layer of the present invention by a dye film represented by a phthalocyanine dye having a special structure as represented by the general formula [I]. That is, the most characteristic feature of the phthalocyanine compound represented by the general formula [I] is that the substituent X is a bulky branched alkoxyl group in which a fluorine atom is substituted 2.
This is to introduce one 2-bis (trifluoromethyl) propoxy group into each of the four benzene rings constituting the phthalocyanine. The substitution position on each benzene ring is not particularly limited and may be any of the four substitutable positions. By introducing such a substituent, stacking due to the overlapping of benzene rings of phthalocyanine molecules is inhibited, and a substituent introduced from the central metal in the direction perpendicular to the molecular plane of the phthalocyanine ring (substitution in general formula [I] Synergistically with the effect of the steric hindrance of the group Z), a higher refractive index can be obtained, so that the reflectance in the structure of the transparent substrate / recording film / reflection film is increased and at the same time the wavelength dependence of the reflectance is reduced. It Further, since the shape and symmetry of the recording pit are improved by the effect of the fluorine atom introduced into the substituent (which is considered to be due to the interface energy between the substrate and the recording film), the distortion of the recording signal is reduced. At the same time, the contrast becomes clear before and after recording,
A high recording modulation degree and a good recording waveform can be obtained. Also, the solubility in general-purpose organic solvents is dramatically improved,
The advantage is that the recording film can be easily formed by the spin coating method. In this way, by introducing a 2,2-bis (trifluoromethyl) propoxy group, which is a bulky branched alkoxyl group having a fluorine atom substituted into the substituent X, the substrate / recording film / reflection film / protective film It can be said that the recording film material has particularly excellent characteristics as a recording film for a write-once compact disc composed of the above laminated body.

The phthalocyanine represented by the general formula [I] of the present invention
Substituent Y introduced into anine dye ¹~ Y^FourHara that constitutes
Typical examples of the organic and organic substituents have no substituent.
In case of hydrogen atom, halogen atom
Include chlorine, bromine, iodine, and fluorine, having a substituent
Examples of the alkyl group that may be used include a methyl group, an n-butyl group,
t-butyl group, stearyl group, trichloromethyl group,
Lifluoromethyl group, 2-methoxyethyl group, Phthali
A methyl group, etc., and an aryl group which may have a substituent
Phenyl group, naphthyl group, p-nitrophenyl
Group, pt-butylphenyl group, etc., having a substituent
As the alkoxy group which may be present, methoxy group, ethoxy group
Group, n-butoxy group and the like, which may have a substituent.
Examples of the reeloxy group include phenoxy group and pentafluor group.
Alkyl having a phenyl group etc., which may have a substituent
Examples of the thio group include a methylthio group and a t-butylthio group.
As an arylthio group which may have a substituent,
Phenylthio group, p-nitrophenylthio, etc.
However, the present invention is not limited to these.

In the present invention, the compound represented by the general formula [I] can be produced, for example, by the following method.

That is, phthalonitriles represented by the following general formula [III], or isoidrin compounds represented by the following general formula [IV], or corresponding phthalic anhydrides and phthalimides represented by the general formula [I]. Medium M
The phthalocyanine compound represented by the general formula [V] can be produced by a conventional method using various metal salts of the metal represented by

General formula [III]

Embedded image [In the formula, X, Y and n have the same meanings as X, Y ^{1 to} Y ⁴ and n ^{1 to} n ⁴ in the general formula [I], respectively. ]

General formula [IV]

Embedded image [In the formula, X, Y and n have the same meanings as X, Y ^{1 to} Y ⁴ and n ^{1 to} n ⁴ in the general formula [I], respectively. ]

General formula [V]

[Chemical 6] ^{Wherein, X, Y 1 ~Y 4,} n 1 ~n 4, M, X in m respectively general formula ^{[I], Y 1 ~Y 4} , n 1 ~n 4, M, the same meaning as m Represent ]

Next, the obtained phthalocyanine compound represented by the general formula [V] is reacted with a chlorophosphine derivative having a linear, branched or cyclic alkyl group or aryl group which may have various substituents. By doing so, the phthalocyanine compound represented by the general formula [I] can be produced.

Typical examples of the phthalocyanine compound represented by the general formula [I] used in the present invention include the phthalocyanine compounds (a) to (e) shown below, but are not limited thereto. Absent.

(A)

[Chemical 7]

(B)

Embedded image

(C)

[Chemical 9]

(D)

[Chemical 10]

(E)

[Chemical 11]

The recording film layer using the phthalocyanine compound represented by the general formula [I] in the present invention is for the purpose of further improving the stability of the recording film such as light resistance and environment resistance, and the stability of repeated reproduction. Additives such as oxygen quencher and ultraviolet absorber may be added.

The recording film layer may be formed by a dry process such as vacuum deposition or sputtering, but a wet process such as spin coating, dipping, spraying, roll coating or It is also possible by the LB (Langmuir-Blodgett) method. The recording film material of the present invention is soluble in general-purpose organic solvents such as alcohol-based, ketone-based, cellosolve-based, halogen-based, hydrocarbon-based, and fluorocarbon-based materials, and therefore spin-coated from the viewpoint of productivity and recording film uniformity. The method of forming a film by the method is preferable.

As described above, when the film is formed by the so-called coating method, a polymer binder may be added if necessary. Examples of the polymer binder include acrylic resin, polycarbonate resin, polyester resin, polyamide resin, vinyl chloride resin, vinyl acetate resin, nitrocellulose, and phenol resin, but are not limited thereto. The mixing ratio of the polymer binder is not particularly limited, but is preferably 30 wt% or less with respect to the dye.

The optimum film thickness of the recording film layer of the present invention is not particularly limited because it depends on the type and combination of recording film materials and is preferably 500 to 3000 A, more preferably 1000 A.
˜2500 A is the optimum film thickness range.

The reflective film material of the present invention includes gold, silver,
Metals such as copper, platinum, aluminum, cobalt, tin, and alloys containing these as main components, MgO, ZnO, SnO
Examples thereof include metal oxides such as SiN4, nitrides such as SiN4, AlN, and TiN. Gold is most preferable because of its high absolute reflectance and excellent stability. In addition, an organic highly reflective film can be used depending on the case. As a method for forming such a reflective film, a dry process such as a vacuum deposition method or a sputtering method is most preferable, but the method is not limited to these. The optimum thickness of the reflective film of the present invention is not particularly limited, but is preferably in the range of 400 to 1300A.

Further, the disk is protected from above the reflective film for the purpose of preventing chemical deterioration (eg, oxidation, water absorption, etc.) and physical deterioration (eg, scratches, scratches, etc.) of the disk, particularly the recording film layer and the reflective film layer. To provide a protective layer. As a material for the protective layer, a method in which an ultraviolet curable resin is used and applied by spin coating and cured by ultraviolet irradiation is preferable, but the material is not limited to this. Regarding the optimum thickness of the protective layer, when it is thin, the protective effect is lowered, and when it is thick, it causes deterioration of mechanical properties such as warpage of the disk due to shrinkage during curing of the resin. It is preferable to form a film in the micron range.

The disk substrate used in the present invention preferably has a light transmittance for writing or reading a signal of 85% or more and a small optical anisotropy. For example, glass, acrylic resin, polycarbonate resin, polyester resin, polyamide resin, vinyl chloride resin, vinyl acetate resin, polystyrene resin, polyolefin resin (poly-4-
Substrates made of a thermoplastic resin such as methylpentene) or a polyether sulfone resin, or a thermosetting resin such as an epoxy resin or an allyl resin can be given. Among these, those made of a thermoplastic resin are preferable from the standpoint of ease of molding and provision of wobble signals for ATIP and guide grooves, etc. Further, acrylic resin and polycarbonate are preferable in view of optical characteristics, mechanical characteristics and cost. Those made of resin are particularly preferable. The ATIP wobble signal and the guide groove are preferably provided by using a stamper or the like when molding (injection molding, compression molding) a thermoplastic resin, but so-called 2P using a photopolymer resin is preferable.
It can also be carried out by the method by law.

The shape of the guide groove of the present invention is not particularly limited and may be trapezoidal or U-shaped. The optimum size of the guide groove varies depending on the type and combination of recording film materials, but the average groove width (width at half the groove depth) is 0.4 to 0.6 μm. ,
Further, the groove depth is preferably in the range of 1000 to 2000A.

Since the disk form of the present invention must function as a CD or CD-ROM after recording,
Alternatively, it preferably conforms to the CD-ROM standard (Red Book) and the write-once compact disc standard (Orange Book).

[0030]

The present invention will be specifically described with reference to the following examples and comparative examples, but the present invention is not limited to the following examples. First, a method for producing a typical example of the phthalocyanine compound used in the present invention will be described.

Production Example 1: Production of phthalocyanine compound (a) 120 parts of sulfolane, 1,8-diazabicyclo [5,5]
4,0] -7-Undecene (14 parts) was added with 4- (2,2-bis (trifluoromethyl) propyl) oxy-1,3-diiminoisoindoline (10 parts) and silicon tetrachloride (5 parts) to give 160-170. After stirring for 8 hours at ℃, cool and
The mixture was poured into a mixed solution of 80 parts of 5% hydrochloric acid and 1500 parts of water and stirred, and the mixture was heated and stirred at 80 ° C. for 2 hours, and the deposited precipitate was separated by filtration, washed with a mixed solution of methanol / water (4/1), dried and dried to give a greenish solution. 10 parts of powder were obtained. This powder was dissolved in 250 parts of concentrated sulfuric acid, poured into 2000 parts of ice water, and the deposited precipitate was separated by filtration, washed with water and dried to obtain 9 parts of greenish blue powder. As a result of FD-MS analysis, this powder was confirmed to be a dihydroxysilicon phthalocyanine compound corresponding to the general formula [V]. After dissolving 5 parts of the dihydroxysilicon phthalocyanine compound obtained above in 100 parts of pyridine and 25 parts of tri-n-butylamine with stirring, 10 parts of chlorodiphenylphosphine was added while cooling, and the mixture was heated with stirring at 110 ° C. for 2 hours, It was cooled and poured into 1000 parts of ice water. The deposited precipitate was separated by filtration, washed with water and dried to obtain 4 parts of the phthalocyanine compound (a).

Production Example 2: Production of phthalocyanine compound (b) In 50 parts of o-dichlorobenzene and 25 parts of tri-n-butylamine, 4- (2,2-bis (trifluoromethyl)) was added.
Propyl) oxy-1,3-diiminoisoindoline 8
Part and 6 parts of silicon tetrachloride were added, and the mixture was heated at 160-170 ° C for 7
After heating and stirring for an hour, the mixture was cooled, diluted with 1000 parts of methanol, the deposited precipitate was separated by filtration, washed with a mixed solution of methanol / water (3/1) and dried to obtain 5.5 parts of a green powder. This powder was dissolved in 300 parts of concentrated sulfuric acid, poured into 6000 parts of ice water, and the deposited precipitate was separated by filtration, washed with water and dried to obtain 4.3 parts of greenish blue powder. As a result of FD-MS analysis, this powder was confirmed to be a hydroxyaluminum phthalocyanine compound corresponding to the general formula [V]. After 4 parts of the hydroxyaluminum phthalocyanine compound obtained above was dissolved in 80 parts of pyridine and 20 parts of tri-n-butylamine by stirring, 5 parts of chlorodiphenylphosphine was added while cooling, and the mixture was heated with stirring at 110 ° C. for 2 hours, It was cooled and poured into 1000 parts of ice water. The deposited precipitate was separated by filtration, washed with water and dried to obtain 3.5 parts of green powder. FD-MS
As a result of the analysis, it was confirmed that this powder was the phthalocyanine compound (b).

Production Example 3: Production of Phthalocyanine Compound (c) In the same manner as in Production Example 2, 150 parts of o-dichlorobenzene,
To 30 parts of tri-n-butylamine, 10 parts of 4- (2,2-bis (trifluoromethyl) propyl) oxy-6-bromo-1,3-diiminoisoindoline and 15 parts of silicon tetrachloride were added, and the amount of 160- After heating and stirring at 170 ° C. for 8 hours, the mixture was cooled and diluted with 2000 parts of methanol. The deposited precipitate was separated by filtration, washed with a mixed solution of methanol / water (4/1) and dried to obtain 8 parts of a green powder. After dissolving this powder in 400 parts of concentrated sulfuric acid, pour into 2000 parts of ice water,
The deposited precipitate was separated by filtration, washed with water and dried to obtain 6 parts of greenish blue powder. As a result of FD-MS analysis, this powder was confirmed to be a dihydroxysilicon phthalocyanine compound corresponding to the general formula [V]. 5 parts of the dihydroxysilicon phthalocyanine compound obtained above was added to 100 parts of pyridine,
After stirring and dissolving in 25 parts of tri-n-butylamine, 10 parts of chlorodiphenylphosphine was added while cooling and 1
After heating and stirring at 10 ° C. for 2 hours, the mixture is cooled and ice water 1000 is added.
Injected into the section. The deposited precipitate was separated by filtration, washed with water and dried to obtain 7 parts of a phthalocyanine compound (c).

Production Example 4: Production of Phthalocyanine Compound (d) In the same manner as in Production Example 2, 200 parts of o-dichlorobenzene,
To 50 parts of tri-n-butylamine, 10 parts of 4- (2,2-bis (trifluoromethyl) propyl) oxy-7-methyl-1,3-diiminoisoindoline and 15 parts of silicon tetrachloride were added, and the amount of 160- After heating and stirring at 170 ° C. for 8 hours, the mixture was cooled and diluted with 1500 parts of methanol. The deposited precipitate was separated by filtration, washed with a mixed solution of methanol / water (4/1) and dried to obtain 8 parts of a green powder. After dissolving this powder in 300 parts of concentrated sulfuric acid, pour into 2000 parts of ice water,
The deposited precipitate was separated by filtration, washed with water and dried to obtain 6 parts of greenish blue powder. As a result of FD-MS analysis, this powder was confirmed to be a dihydroxysilicon phthalocyanine compound corresponding to the general formula [V]. 5 parts of the dihydroxysilicon phthalocyanine compound obtained above was dissolved in 70 parts of pyridine and 20 parts of tri-n-butylamine with stirring, and then 10 parts of chlorodiphenylphosphine was added while cooling.
After heating and stirring at 0 ° C. for 2 hours, the mixture was cooled and poured into 1000 parts of ice water. The deposited precipitate was separated by filtration, washed with water and dried to obtain 4 parts of phthalocyanine compound (d).

Production Example 5: Production of phthalocyanine compound (e) 96% of 5 parts of dihydroxysilicon phthalocyanine compound corresponding to the general formula [V] synthesized in the same manner as in Production Example 1 was produced.
Dissolve it in 550 parts of concentrated sulfuric acid and add 11 parts of bromine to adjust the system temperature to 2
After stirring for 6 hours while maintaining the temperature at 5-30 ° C, the mixture was poured into 2000 parts of water in which 24 parts of sodium hydrogen sulfite was dissolved and stirred, and the deposited precipitate was separated by filtration, an aqueous sodium hydrogencarbonate solution,
It was washed successively with water and a mixed solution of methanol / water (1/1) and dried to obtain 5.2 parts of a green powder. This powder is FD-M
As a result of S analysis, it was confirmed to be a dihydroxysilicon phthalocyanine compound corresponding to the general formula [V], which is a mixture having a bromination degree of 1 to 4. 5 parts of the dihydroxysilicon phthalocyanine body obtained above was added to pyridine 100
And 25 parts of tri-n-butylamine with stirring,
While cooling, 10 parts of chlorodiphenylphosphine was added, and the mixture was heated and stirred at 110 ° C. for 2 hours and then cooled, and ice water 1
It was poured into 000 parts. The deposited precipitate was separated by filtration, washed with water and dried to obtain 4 parts of a phthalocyanine compound (e).

Example 1 Depth 1200 Angstroms, Width 0.50 microns,
1.20m thickness with guide grooves with pitch of 1.6 microns
m, an outer diameter of 120 mm, an inner diameter of 15 mm, a phthalocyanine compound [a] was added to a 2, 2, 3,
The solution was dissolved in 3-tetrafluoropropanol at a concentration of 50 mg / ml, 0.2 micron filtering was performed to adjust a coating solution, and the coating solution was used to form a film having a recording film thickness of 1300 angstroms by a spin coater. next,
Gold was deposited on the recording film thus obtained by sputtering to have a film thickness of 800 Å. further,
An optical disk was prepared by forming a protective film layer of 5 μm thick with an ultraviolet curable resin on this. The reflectance of the optical disk thus produced was 76%. Using the optical disk thus produced, a semiconductor laser with a wavelength of 785 nm was used and the EF at a linear velocity of 1.4 m / sec.
When an M-CD format signal was recorded, it was possible to record at an optimum recording laser power of 6.1 mW. Next, when this signal was reproduced by a CD player with a laser power of 0.5 mW, the obtained signal was good, and the level was sufficiently high for a commercially available CD player.

Example 2 1200 Angstroms deep, 0.50 micron wide,
1.20m thickness with guide grooves with pitch of 1.6 microns
m, an outer diameter of 120 mm, and an inner diameter of 15 mm, a phthalocyanine compound [b] was dissolved in diacetone alcohol at a concentration of 60 mg / ml, and the coating liquid was adjusted by performing 0.2 micron filtering. A spin coater was used to form a recording film having a film thickness of 1200 Å. Next, gold was formed into a film having a thickness of 800 angstrom on the recording film thus obtained by sputtering. Further, a protective film layer having a film thickness of 5 μm was formed thereon by an ultraviolet curable resin to form an optical disk. The reflectivity of the optical disk thus created was 80%. Using the optical disk thus created, a semiconductor laser with a wavelength of 785 nm was used, and an EFM-CD format signal was obtained at a linear velocity of 1.4 m / sec. Was recorded, the optimum recording laser power was 6.5.
Recording was possible at mW. Next, when this signal was reproduced by a CD player with a laser power of 0.5 mW, the obtained signal was good, and the level was sufficiently high for a commercially available CD player.

Examples 3-4 Depth 1250 Angstroms, Width 0.48 microns,
1.20m thickness with guide grooves with pitch of 1.6 microns
m, an outer diameter of 120 mm, and an inner diameter of 15 mm, the phthalocyanine compound shown in Table 1 was dissolved in diacetone alcohol at a concentration of 60 mg / ml to give 0.2
Micron filtering was performed to adjust the coating liquid, and the coating liquid was used to form a film having a recording film thickness of 1200 Å by a spin coater. Next, gold was formed into a film having a thickness of 800 angstrom on the recording film thus obtained by sputtering. Further, a protective film layer having a film thickness of 5 μm was formed thereon by an ultraviolet curable resin to form an optical disk. Table 1 shows the reflectance of the optical disk thus prepared and the optimum laser power when recording and reproducing were performed by the same method as in Example 1. Table 1 ─────────────────────────────────── Examples Examples Phthalocyanine reflectance Optimum recording compound% Laser power (mW ) ─────────────────────────────────── 3 (c) 75 6.3 4 (d) 736 . 9 ───────────────────────────────────

Comparative Example 1 An optical disk was prepared in the same manner as in Example 1 except that the phthalocyanine compound represented by the chemical formula [VI] was used. Chemical formula [VI]

[Chemical 12] The reflectance of the optical disk thus produced was 51%. Using the optical disk thus produced, a semiconductor laser with a wavelength of 785 nm was used to obtain a linear velocity of 1.4 m.
When the EFM-CD format signal was recorded at / sec, the optimum recording laser power was 8.9 mW.

Comparative Example 2 An optical disk was prepared in the same manner as in Example 1 except that the phthalocyanine compound represented by the chemical formula [VII] was used.
Chemical formula [VII]

[Chemical 13] The reflectance of the optical disk thus produced was 62%. Using the optical disk thus produced, a semiconductor laser having a wavelength of 785 nm was used to obtain a linear velocity of 1.4 m.
When the EFM-CD format signal was recorded at / sec, the optimum recording laser power was 7.7 mW.

[0041]

As is apparent from Examples 1 to 5 and Comparative Examples 1 and 2, 2,2-bis (trifluoromethyl) propoxy, which is a branched alkoxyl group as the substituent X in the general formula [I], is used. By introducing a group, a light showing stable recording / reproducing characteristics with higher sensitivity and higher reflectance for a semiconductor laser of 780 nm to 810 nm than a phthalocyanine compound having a linear type substituent up to now. A recording medium can be provided.

Continuation of front page (56) Reference JP-A-63-312888 (JP, A) JP-A-63-313760 (JP, A) JP-A-2-160583 (JP, A) JP-A-3-281388 (JP , A) JP-A-4-270686 (JP, A) JP-A-5-73957 (JP, A) JP-A-5-139044 (JP, A)

Claims (3)

(57) [Claims] 1. An optical recording medium comprising a laminate of transparent substrate / recording film / reflection film / protective film, wherein the recording film contains a phthalocyanine compound represented by the following general formula [I]. General formula [I] [In the formula, the substituent X represents a 2,2-bis (trifluoromethyl) propoxy group. The substituents Y ^{1 to} Y ⁴ are each independently a halogen atom, an alkyl group which may have a substituent,
An aryl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, and a substituent also good arylthio group, a nitro group, a cyano group, a sulfonic acid group, a sulfonic acid amide group, a sulfonic acid ester group, n1 to n4 represents an integer of 0 to 3 in the number of substituents Y ¹ to Y ^4. The central metal M represents Si or Al. The substituent ^{Z, -OP (= O) R 1} R 2 or -OP (= O)
Represents Ar ¹ Ar ² . However, R ¹ and R ² represent a linear, branched or cyclic alkyl group which may have a substituent, and A 1
r ¹ and Ar ² represent an aryl group which may have a substituent.
m represents the number of substituents Z and is an integer of 1 or 2. ] 2. A recording film material for an optical recording medium according to claim 1, comprising a phthalocyanine compound represented by the general formula [I]. 3. A phthalocyanine compound represented by the following formula [II]:
The recording film material according to claim 2, wherein Formula [II]