Optical information recording medium near infrared absorbing material therefor

• US 5,677,025 A
• Filed: 06/12/1995
• Issued: 10/14/1997
• Est. Priority Date: 09/09/1993
• Status: Expired due to Fees

• Current Assignee: Ricoh Company Limited
• Original Assignee: Ricoh Company Limited
• Inventors: Sato, Tsutomu, Sasa, Noboru, Tomura, Tatsuya
• Primary Examiner(s): Ryan, Patrick J.
• Assistant Examiner(s): MULVANEY, ELIZABETH EVANS
• Application Number:
  US08/433,454
• Time in Patent Office: 855 Days
• Field of Search: 428/64.1, 428/64.2, 428/64.4, 428/64.7, 428/64.8, 428/457, 428/412, 428/913, 430/270, 430/271, 430/495, 430/945, 369/283, 369/288
• US Class Current: 430/270.16
• CPC Class Codes: C09B 47/0675 having oxygen or sulfur linked directly to the skeleton
• CPC Class Codes: G11B 7/248 porphines; azaporphines, e.g. phthalocyanines
• CPC Class Codes: Y10S 428/913 Material designed to be responsive to temperature, light, moisture
• CPC Class Codes: Y10S 430/146 Laser beam

Abstract

Disclosed are a phthalocyanine near infrared absorbing material having a phthalocyanine skeleton whose benzene rings contain a silyl group as a bulky substituent and an optical information recording medium containing the material.

The phthalocyanine near infrared absorbing material has excellent association-preventing property and light resistance and exhibits a high index of refraction at a wave length of 770-830 nm and high stability, an optical information recording medium (CD-R recording medium) containing the phthalocyanine has high reflectance, excellent storage stability and excellent reproduction stability. The recording medium also shows strong light absorptivity and light reflectivity in a wave length of 630-700 nm and, thus, is applicable for the pick up with a semiconductor laser of 630-700 nm, permitting such high density recording as to provide 1.6-1.7 times as high recording density as that attained by currently employed recording media which are adapted to 780-810 nm.

Claims

1. An optical information recording medium comprising a substrate, a recording layer provided directly or through a primer layer on said substrate, and, optionally, a protecting layer provided on said recording layer, wherein said recording layer contains a phthalocyanine compound having the following general formula (I) ##STR56## wherein M, X¹ -X⁴ and k-n represent as follows:

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

X¹ -X⁴ ;

independently from each other, a --OR¹ SiR² R³ R⁴ group,

R¹ ;

independently from each other, a substituted or non-substituted divalent aliphatic hydrocarbon group, a substituted or non-substituted divalent aliphatic hydrocarbon group having an ether linkage, a substituted or non-substituted divalent aromatic hydrocarbon group, or a substituted or non-substituted divalent aromatic heterocyclic group,

R² -R⁴ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a --OR⁹ group,

R⁹ ;

a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a silyl group, and

k, l, m, n;

independently from each other, an integer of 0-4 with the proviso that not all of k, l, m and n are simultaneously zero and that when k, l, m and n are each 3 or less the other substituent or substituents on respective benzene rings are hydrogen atoms or halogen atoms.

5. An optical information recording medium as recited in claim 1, characterized in that a reflecting metal layer is provided between said recording layer and said protecting layer so that said recording medium is of a WORM type compact disc for recording signals of a CD format.

2. An optical information recording medium wherein the phthalocyanine compound is one or a mixture of two or more of the four compounds having the following general formulas (II-a)-(II-d):

##STR57## wherein M and X¹ -X¹⁶ represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

X¹ -X¹⁶ ;

independently from each other, a --OR¹ SiR² R³ R⁴ group,

R¹ ;

independently from each other, a substituted or non-substituted divalent aliphatic hydrocarbon group, a substituted or non-substituted divalent aliphatic hydrocarbon group having an ether linkage, a substituted or non-substituted divalent aromatic hydrocarbon group, or a substituted or non-substituted divalent aromatic heterocyclic group,

R² -R⁴ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a --OR⁹ group,

R⁹ ;

a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a silyl group, and

atoms, other than X¹ -X¹⁶, bonded to the benzene ring;

hydrogen atoms or halogen atoms.

3. An optical information recording medium wherein the phthalocyanine compound is one or a mixture of two or more of the four compounds having the following general formulas (III-a)-(III-d):

##STR58## wherein M and X¹ -X¹⁶ represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

X¹ -X¹⁶ ;

independently from each other, a --OR¹ SiR² R³ R⁴ group,

R¹ ;

independently from each other, a substituted or non-substituted divalent aliphatic hydrocarbon group, a substituted or non-substituted divalent aliphatic hydrocarbon group having an ether linkage, a substituted or non-substituted divalent aromatic hydrocarbon group, or a substituted or non-substituted divalent aromatic heterocyclic group,

R² -R⁴ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a --OR⁹ group,

R⁹ ;

a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a silyl group, and

atoms, other than X¹ -X¹⁶, bonded to the benzene ring;

hydrogen atoms or halogen atoms.

4. An optical information recording medium wherein the phthalocyanine compound is one or a mixture of two or more of the four compounds having the following general formulas (IV-a)-(IV-d):

##STR59## wherein M, X¹ -X¹⁶, Y and n1-n4 represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

X¹ -X¹⁶ ;

independently from each other, a --OR¹ SiR² R³ R⁴ group,

R¹ ;

independently from each other, a substituted or non-substituted divalent aliphatic hydrocarbon group, a substituted or non-substituted divalent aliphatic hydrocarbon group having an ether linkage, a substituted or non-substituted divalent aromatic hydrocarbon group, or a substituted or non-substituted divalent aromatic heterocyclic group,

R² -R⁴ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a --OR⁹ group,

R⁹ ;

a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic heterocyclic group, or a silyl group,

atoms, other than X¹ -X¹⁶, bonded to the benzene ring;

hydrogen atoms or halogen atoms,

Y;

a halogen atom, and

n1-n4;

independently from each other, an integer of 1-4 showing the number of the halogen substituents.

6. A phthalocyanine-type near infrared absorbing material comprising one or a mixture of two or more of the four compounds having the following general formulas (II'"'"'-a)-(II'"'"'-d):

##STR60## wherein M and X¹ -X¹⁶ represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

X¹ -X¹⁶ ;

independently from each other, a --OR¹¹ SiR¹² R¹³ R¹⁴ group,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

R¹¹ ;

a straight chain or branched alkylene group which has 1-8 carbon atoms and which may contain a so-called ether linkage of --C--O--C-- and may be substituted with a silyl group,

R¹² -R¹⁴ ;

independently from each other, a hydrogen atom, an alkyl group having 1-12 carbon atoms, an alkoxy group having 1-3 carbon atoms, a vinyl group, a --OSi(R¹⁵)₃ group or a --CH₂ Si(R¹⁵)₃ group,

R¹⁵ ;

an alkyl group having 1-3 carbon atoms, and

atoms, other than X¹ -X¹⁶, bonded to the benzene ring;

hydrogen atoms or halogen atoms.

7. A phthalocyanine-type near infrared absorbing material comprising one or a mixture of two or more of the four compounds having the following general formulas (III'"'"'-a)-(III'"'"'-d):

##STR61## wherein M and X¹ -X¹⁶ represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

X¹ -X¹⁶ ;

independently from each other, a --OR¹¹ SiR¹² R¹³ R¹⁴ group,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

R¹¹ ;

a straight chain or branched alkylene group which has 1-8 carbon atoms and which may contain a so-called ether linkage of --C--O--C-- and may be substituted with a silyl group,

R¹² -R¹⁴ ;

independently from each other, a hydrogen atom, an alkyl group having 1-12 carbon atoms, an alkoxy group having 1-3 carbon atoms, a vinyl group, a --OSi(R¹⁵)₃ group or a --CH₂ Si(R¹⁵)₃ group,

R¹⁵ ;

an alkyl group having 1-3 carbon atoms, and

atoms, other than X¹ -X¹⁶, bonded to the benzene ring;

hydrogen atoms or halogen atoms.

8. A phthalocyanine-type near infrared absorbing material comprising one or a mixture of two or more of the four compounds having the following general formulas (IV'"'"'-a)-(IV'"'"'-d):

##STR62## wherein M, X¹ -X¹⁶, Y and n1-n4 represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q,

X¹ -X¹⁶ ;

independently from each other, a --OR¹¹ SiR¹² R¹³ R¹⁴ group,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

R¹¹ ;

a straight chain or branched alkylene group which has 1-8 carbon atoms and which may contain a so-called ether linkage of --C--O--C-- and may be substituted with a silyl group,

R¹² -R¹⁴ ;

independently from each other, a hydrogen atom, an alkyl group having 1-12 carbon atoms, an alkoxy group having 1-3 carbon atoms, a vinyl group, a --OSi(R¹⁵)₃ group or a --CH₂ Si(R¹⁵)₃ group,

R¹⁵ ;

an alkyl group having 1-3 carbon atoms,

atoms, other than X¹ -X¹⁶, bonded to the benzene ring;

hydrogen atoms or halogen atoms,

Y;

a halogen atom, and

n1-n4;

independently from each other, an integer of 1-4 showing the number of the halogen substitution.

9. A phthalocyanine-type near infrared absorbing material having the following general formula (V):

##STR63## wherein M and X¹ -X⁴ represent as follows;

M;

two hydrogen atoms, a metal atom which may contain halogen or oxygen atoms, or a metal atom which may contain --(OR⁵)_p or --(OSiR⁶ R⁷ R⁸)_q, and

X¹ -X⁴ ;

independently from each other, a --OR¹¹ SiR¹² R¹³ R¹⁴ group,

R⁵ -R⁸ ;

independently from each other, a hydrogen atom, a substituted or non-substituted monovalent aliphatic hydrocarbon group, a substituted or non-substituted monovalent aromatic hydrocarbon group, or a substituted or non-substituted monovalent aromatic heterocyclic group,

p, q;

an integer of 0-2,

R¹¹ ;

a straight chain or branched alkylene group which has 1-5 carbon atoms and which may contain a so-called ether linkage of --C--O--C-- and may be substituted with a silyl group,

R¹² -R¹⁴ ;

independently from each other, a hydrogen atom, an alkyl group having 1-12 carbon atoms, an alkoxy group having 1-3 carbon atoms, a vinyl group, a --OSi(R¹⁵)₃ group or a --CH₂ Si(R¹⁵)₃ group,

R¹⁵ ;

an alkyl group having 1-3 carbon atoms.