Optical recording medium

• US 6,197,477 B1
• Filed: 08/18/1999
• Issued: 03/06/2001
• Est. Priority Date: 08/18/1998
• Status: Expired due to Fees

• Current Assignee: Ricoh Company Limited
• Original Assignee: Ricoh Company Limited
• Inventors: Higashi, Yasuhiro, Maruyama, Shohji, Satoh, Tsutomu, Sasa, Noboru, Ueno, Yasunobu, Tomura, Tatsuya
• Primary Examiner(s): ANGEBRANNDT, MARTIN J
• Application Number:
  US09/376,197
• Time in Patent Office: 566 Days
• Field of Search: 430/270.16, 430/945, 428/64.8, 369/288, 534/707, 534/723, 534/713
• US Class Current: 430/270.16
• CPC Class Codes: G11B 7/00455 involving reflectivity, absorption or colour changes
• CPC Class Codes: G11B 7/0052 involving reflectivity, absorption or colour changes
• CPC Class Codes: G11B 7/127 Lasers; Multiple laser arrays lasers per se H01S
• CPC Class Codes: G11B 7/2467 azo-dyes
• CPC Class Codes: G11B 7/2472 cyanine
• CPC Class Codes: G11B 7/248 porphines; azaporphines, e.g. phthalocyanines
• CPC Class Codes: G11B 7/249 containing organometallic compounds G11B7/246 takes precedence
• CPC Class Codes: G11B 7/258 of reflective layers
• CPC Class Codes: Y10S 430/146 Laser beam

Abstract

An optical recording material including a substrate and a recording layer which is formed overlying the substrate, wherein the recording layer includes an azo chelate compound including an azo compound and at least one of a metal and a metal salt, and wherein the azo compound has the following formula (1):

Claims

1. An optical recording material comprising a substrate and a recording layer which is formed overlying the substrate, wherein the recording layer comprises an azo chelate compound comprising an azo compound and at least one of a metal and a metal salt and wherein the azo compound has the following formula (1):

wherein R1, R2 and R3 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an amino group, a carbamoyl group, an alkyl group which may be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted, an alkyloxy group which may be substituted, an aryloxy group which may be substituted, an alkylamino group which may be substituted, an arylamino group which may be substituted, an alkyloxycarbonyl group which may be substituted, an aryloxycarbonyl group which may be substituted, an alkylcarbonylamino group which may be substituted, an arylcarbonylamino group which may be substituted, an alkylcarbamoyl group which may be substituted, an arylcarbamoyl group which may be substituted or an alkenyl group which may be substituted;

R4 and R5 independently represent a hydrogen atom, an alkyl group which may be substituted or an aryl group which may be substituted, wherein R1 and R2, R2 and R4, R2 and R5, R3 and R4, R3 and R5, and R4 and R5 may combine to form a ring;

X1 represents a group of R6 or SR7, wherein R6 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an alkyl group which may be substituted, a phenyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, a carbamoyl group which may be substituted, an acyl group which may be substituted, an alkoxycarbonyl group which may be substituted, an aryloxycarbonyl group which may be substituted, an alkenyl group which may be substituted or an amino group which may be substituted, and R7 represents a hydrogen atom, an alkyl group which may be substituted, or an aryl group which may be substituted;

X2 represents a group of R8, SR9, OR10 or NR11R12, wherein R8 represents the same groups as mentioned above for use as R6, R9 represents an alkyl group which may be substituted, and R10, R11 and R12 independently represent an alkyl group which may be substituted or an aryl group which may be substituted; and

Z represents a group having active hydrogen.

2. The optical recording medium according to claim 1, wherein Z is a group selected from the group consisting of a hydroxy group and its derivatives, a carboxyl group and its derivatives, an amino group and its derivatives, a sulfo group and its derivatives, an amide group NHX3 in which X3 represents COR13 in which R13 represents an alkyl group which may be substituted or an aryl group which may be substituted, and a sulfonamide group NHX4 in which X4 represents a group of SO₂R14 in which R14 represents an alkyl group which may be substituted or an aryl group which may be substituted.

3. The optical recording medium according to claim 1, wherein the azo compound comprises a compound having the following formula (2):

wherein R15 represents a phenyl group which may be substituted;

R17 and R18 independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted or a phenyl group which may be substituted, wherein R17 and R18 may combine to form a ring;

X3 represents a group of OR19 or NR20R21, wherein R19, R20 and R21 independently represent an alkyl group having 1 to 6 carbon atoms which may be substituted or a phenyl group which may be substituted; and

R16 represents a group of COR22 or SO₂R23, wherein R22 and R23 independently represent an alkyl group which may be substituted or an aryl group which may be substituted.

4. The optical recording medium according to claim 1, wherein the azo compound comprises a compound having the following formula (3):

wherein R24 represents an alkyl group which may be substituted or a phenyl group which may be substituted;

R25 and R26 independently represent a hydrogen atom, an alkyl group which may be substituted or an aryl group which may be substituted, wherein R25 and R26 may combine to form a ring; and

Z1 represents a group of COR27 or SO₂R28, wherein R27 and R28 independently represent an alkyl group which may be substituted or an aryl group which may be substituted.

5. The optical recording medium according to claim 1, wherein the metal comprises a metal selected from the group consisting of manganese, chromium, iron, cobalt, nickel and copper.

6. The optical recording medium according to claim 1, wherein the recording layer has a refractive index n of from about 1.5 to about 3.0 and an extinction coefficient k of from about 0.02 to about 0.2 when the refractive index and the extinction coefficient are measured with respect to only the recording layer using light having a wavelength within ±

5 nm of a wavelength of light used for reproduction.

7. The optical recording medium according to claim 1, wherein the azo chelate compound has a property such that a slope of a weight decreasing curve is greater than about 2%/°

C. during a main weight decreasing process when the azo chelate compound is subjected to a thermogravimetry analysis.

8. The optical recording medium according to claim 1, wherein the azo chelate compound has a property such that total weight loss of the azo chelate compound during a main weight decreasing process is not less than about 30% and a weight decrease starting temperature is not higher than about 350°

C. when the azo chelate compound is subjected to a thermogravimetry analysis.

9. The optical recording medium according to claim 1, wherein the substrate has guide grooves having a track pitch of from about 0.7 to about 0.8 μ

m and a half width of from about 0.18 to about 0.36 μ

m.

10. The optical recording medium according to claim 1, wherein the recording layer further comprises a dye having maximum absorption in a wavelength range of from about 680 to about 750 nm.

11. The optical recording medium according to claim 10, wherein the dye having maximum absorption in a wavelength range of from about 680 to about 750 nm comprises a cyanine dye, a phthalocyanine dye or an azo metal chelate compound.

12. The optical recording medium according to claim 1, wherein the optical recording medium further comprises a light reflective layer, and wherein the light reflective layer comprises a metal selected from the group consisting of gold, gold alloys, silver, silver alloys, aluminum and aluminum alloys.

13. An optical information recording and reproducing method comprising the steps of:

providing an optical recording medium comprising a substrate and a recording layer which is formed overlying the substrate, wherein the recording layer comprises an azo metal chelate compound comprising an azo compound and a metal or a metal salt, and wherein the azo compound has the following formula (1);

wherein R1, R2 and R3 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an amino group, a carbamoyl group, an alkyl group which may be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted, an alkyloxy group which may be substituted, an aryloxy group which may be substituted, an alkylamino group which may be substituted, an arylamino group which may be substituted, an alkyloxycarbonyl group which may be substituted, an aryloxycarbonyl group which may be substituted, an alkylcarbonylamino group which may be substituted, an arylcarbonylamino group which may be substituted, an alkylcarbamoyl group which may be substituted, an arylcarbamoyl group which may be substituted or an alkenyl group which may be substituted;

R4 and R5 independently represent a hydrogen atom, an alkyl group which may be substituted or an aryl group which may be substituted, wherein R1 and R2, R2 and R4, R2 and R5, R3 and R4, R3 and R5, and R4 and R5 may combine to form a ring;

X1 represents a group of R6 or SR7, wherein R6 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an alkyl group which may be substituted, a phenyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, a carbamoyl group which may be substituted, an acyl group which may be substituted, an alkoxycarbonyl group which may be substituted, an aryloxycarbonyl group which may be substituted, an alkenyl group which may be substituted or an amino group which may be substituted, and R7 represents a hydrogen atom, an alkyl group which may be substituted, or an aryl group which may be substituted;

X2 represents a group of R8, SR9, OR10 or NR11R12, wherein R8 represents the same groups as mentioned above for use as R6, R9 represents an alkyl group which may be substituted, and R10, R11 and R12 independently represent an alkyl group which may be substituted or an aryl group which may be substituted; and

Z represents a group having active hydrogen;

irradiating the optical recording medium with laser light to record information in the optical recording medium; and

irradiating the optical recording medium, in which information is recorded, with laser light which may be different from or the same as said first-mentioned laser light to reproduce the information,

wherein the first-mentioned laser light and the second-mentioned laser light have a wavelength of from about 630 to about 690 nm.

14. The optical information recording and reproducing method according to claim 13, wherein the recording layer has a refractive index n of from about 1.5 to about 3.0 and an extinction coefficient k of from about 0.02 to about 0.2 when the refractive index and the extinction coefficient are measured with respect to only the recording layer using light having a wavelength within ±

5 nm of a wavelength of said second-mentioned laser light.

15. An optical information recording and reproducing method comprising the steps of:

providing an optical recording medium comprising a substrate and a recording layer which is formed overlying the substrate, wherein the recording layer comprises a dye having maximum absorption in a wavelength range of from about 680 to about 750 nm, and an azo metal chelate compound comprising an azo compound and a metal or a metal salt, and wherein the azo compound has the following formula (1);

wherein R1, R2 and R3 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an amino group, a carbamoyl group, an alkyl group which may be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted, an alkyloxy group which may be substituted, an aryloxy group which may be substituted, an alkylamino group which may be substituted, an arylamino group which may be substituted, an alkyloxycarbonyl group which may be substituted, an aryloxycarbonyl group which may be substituted, an alkylcarbonylamino group which may be substituted, an arylcarbonylamino group which may be substituted, an alkylcarbamoyl group which may be substituted, an arylcarbamoyl group which may be substituted or an alkenyl group which may be substituted;

R4 and R5 independently represent a hydrogen atom, an alkyl group which may be substituted or an aryl group which may be substituted, wherein R1 and R2, R2 and R4, R2 and R5, R3 and R4, R3 and R5, and R4 and R5 may combine to form a ring;

X1 represents a group of R6 or SR7, wherein R6 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxyl group, an alkyl group which may be substituted, a phenyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, a carbamoyl group which may be substituted, an acyl group which may be substituted, an alkoxycarbonyl group which may be substituted, an aryloxycarbonyl group which may be substituted, an alkenyl group which may be substituted or an amino group which may be substituted, and R7 represents a hydrogen atom, an alkyl group which may be substituted, or an aryl group which may be substituted;

X2 represents a group of R8, SR9, OR10 or NR11R12, wherein R8 represents the same groups as mentioned above for use as R6, R9 represents an alkyl group which may be substituted, and R10, R11 and R12 independently represent an alkyl group which may be substituted or an aryl group which may be substituted; and

Z represents a group having active hydrogen;

irradiating the optical recording medium with laser light to record information in the optical recording medium; and

irradiating the optical recording medium, in which information is recorded, with laser light which may be different from or the same as said first-mentioned laser light to reproduce the information,

wherein the first-mentioned laser light has a wavelength of from about 770 to about 810 nm, and the second-mentioned laser light has a wavelength of from about 630 to about 690 nm or from about 770 to about 810 nm.

16. The optical information recording and reproducing method according to claim 15, wherein the recording layer has a refractive index n of from about 1.5 to about 3.0 and an extinction coefficient k of from about 0.02 to about 0.2 when the refractive index and the extinction coefficient are measured with respect to only the recording layer using light having a wavelength within ±

5 nm of a wavelength of said second-mentioned laser light.