Optical data stores containing a Co-phthalocyanine complex...

Details Optical data stores containing a Co-phthalocyanine complex... Optical data stores containing a Co-phthalocyanine complex...

2001-09-20

2004-03-30

Mulvaney, Elizabeth (Department: 1774)

Stock material or miscellaneous articles

Circular sheet or circular blank

C428S064800, C430S270190, C430S270200

Reexamination Certificate

active

06713146

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to the use of Co-phthalocyanine complexes and a light-absorbing compound in the information layer of recordable optical data media, which information layer is recordable using light, optical data media, and a process for their production.
The singly recordable compact disc (CD-R) has recently been experiencing an enormous growth in quantity. The light-absorbing compound of the information layer represents a substantial component of the optical data medium and has to meet correspondingly high and varied requirements. Not infrequently, the preparation of such compounds is correspondingly complicated (cf. WO-A 00/09522).
It is accordingly an object of the invention to provide a phthalocyanine dye that is simple to synthesize and meets the high requirements (such as light stability, advantageous signal
oise ratio, high recording sensitivity, damage-free application of the substrate material, and the like) for use as a light-absorbing compound in the information layer of a singly recordable optical data medium (chiefly CD-R).
It has surprisingly been found that Co-phthalocyanine complexes are suitable for this purpose.
SUMMARY OF THE INVENTION
The invention relates to an optical data medium containing a transparent substrate, on the surface of which are applied at least one recordable information layer that is recordable using light and optionally a reflection layer, optionally one or more intermediate layers, and/or optionally a protective layer, wherein the information layer contains, as a light-absorbing compound, at least one Co-phthalocyanine complex of the formula (I)
in which
CoPc represents cobalt(III) phthalocyanine,
L
1
and L
2
are axial, coordinately bonded ligands of the cobalt central atom and represent an amine of the formula NR
0
R
1
R
2
or represent an isonitrile of the formula
 in which
R
0
, R
1
, and R
2
independently of one another, represent hydrogen, alkyl, cycloalkyl, alkenyl, aryl, or hetaryl or two of the radicals R
0
to R
2
, together with the N atom to which they are bonded, form a hydrogenated, partly hydrogenated, quasiaromatic, or aromatic ring (preferably a 5- to 7-membered ring) that optionally contains further heteroatoms (particularly from the group consisting of N, O, and/or S),
R represents alkyl, cycloalkyl, alkenyl, aryl, or hetaryl, and
R
3
, R
4
, R
5
, and R
6
are substituents of phthalocyanine and, independently of one another, represent halogen, cyano, alkyl, aryl, alkylamino, dialkylamino, alkoxy, alkylthio, aryloxy, arylthio, SO
3
H, SO
2
NR
7
R
8
, CO
2
R
12
, CONR
7
R
8
, NH—COR
12
, or a radical —(B)
m
—D in which
B denotes a bridge member from the group consisting of a direct bond, CH
2
, CO, CH(alkyl), C(alkyl)
2
, NH, S, O, or —CH═CH—, such that (B)
m
denotes a chemically expedient sequence of bridge members B where m is 1 to 10 (preferably 1, 2, 3, or 4),
D represents the monovalent radical of a redox system of the formula
 or
 or represents a metallocenyl radical or metallocenylcarbonyl radical in which titanium, manganese, iron, ruthenium, or osmium is suitable as a metal center, in which
X
1
and X
2
, independently of one another, represent NR′R″, OR″, or SR″,
Y
1
represents NR′, O, or S, Y
2
represents NR′,
n represents 1 to 10, and
R′ and R″, independently of one another, represent hydrogen, alkyl, cycloalkyl, aryl, or hetaryl, or form a direct bond or a bridge to one of the C atoms of the
 chain,
w, x, y, and z, independently of one another, represent 0 to 12 and w+x+y+z are 12,
R
7
and R
8
, independently of one another, represent alkylamino, hydroxy alkylamino, dialkylamino, bishydroxyalkylamino, or arylamino, or R
7
and R
8
, together with the N atom to which they are bonded, form a heterocyclic 5-, 6-, or 7-membered ring, optionally with participation of further heteroatoms (particularly from the group consisting of O, N, and S, such that NR
7
R
8
represents in particular pyrrolidino, piperidino, or morpholino),
R
12
represents alkyl, aryl, hetaryl, or hydrogen, and
An
−
represents an anion, particularly halide, C
1
- to C
20
-alkylCOO
−
, formate, oxalate, lactate, glycolate, citrate, CH
3
OSO
3
−
, NH
2
SO
3
−
, CH
3
SO
3
−
, ½ SO
4
2−
, or ⅓ PO
4
3−
.
DETAILED DESCRIPTION OF THE INVENTION
The Co-phthalocyanine complex of the formula (I) may also be present in the form of formula (Ia)
in which
CoPc, L
2
, the radicals R
3
-R
6
, and the indices w, x, y, and z have the same meaning as in formula (I), and
R
11
is a covalently bonded radical of the cobalt central atom and derived from the primary or secondary amine or from the isonitrile in the meaning of L
1
(i.e., —NR
1
R
2
, R
1
and R
2
having the above-mentioned meaning, or
For the sake of simplicity, however, the following statements all relate to the compounds of the formula (I) and, of course, also apply in the same manner to the formula (Ia).
Preferred heterocyclic amine ligands in the meaning of L
1
and L
2
are morpholine, piperidine, piperazine, pyridine, 2,2-bipyridine, 4,4-bipyridine, pyridazine, pyrimidine, pyrazine, imidazole, benzimidazole, isoxazole, benzisoxazole, oxazole, benzoxazole, thiazole, benzothiazole, quinoline, pyrrole, indole, and 3,3-dimethylindole, which are coordinated in each case at the nitrogen atom with the cobalt atom.
The alkyl, alkoxy, aryl, and heterocyclic radicals can optionally carry further radicals, such as alkyl, halogen, hydroxyl, hydroxyalkyl, amino, alkylamino, dialkylamino, nitro, cyano, CO—NH
2
, alkoxy, alkoxycarbonyl, morpholino, piperidino, pyrrolidino, pyrrolidono, trialkylsilyl, trialkylsiloxy, or phenyl. The alkyl and alkoxy radicals may be saturated, unsaturated, straight-chain, or branched, the alkyl radicals may be partly halogenated or perhalogenated, and the alkyl and alkoxy radicals can be ethoxylated or propoxylated or silylated. Neighboring alkyl and/or alkoxy radicals on aryl or heterocyclic radicals can together form a three- or four-membered bridge.
Preferred compounds of the formula (I) are those in which the following are true for the radicals R
0
to R
8
and R, R′, R″, and R
12
and for the ligands L
1
and L
2
:
substituents having the designation “alkyl” preferably denote C
1
-C
16
-alkyl (particularly C
1
-C
6
-alkyl), which are optionally substituted by halogen (such as chlorine, bromine, or fluorine), hydroxyl, cyano, and/or C
1
-C
6
-alkoxy;
substituents having the designation “alkoxy” preferably denote C
1
-C
16
-alkoxy (particularly C
1
-C
6
-alkoxy), which are optionally substituted by halogen (such as chlorine, bromine, or fluorine), hydroxyl, cyano, and/or C
1
-C
6
-alkyl;
substituents having the designation “cycloalkyl” preferably denote C
4
-C
8
-cycloalkyl (particularly C
5
-C
6
-cycloalkyl), which are optionally substituted by halogen (such as chlorine, bromine, or fluorine), hydroxyl, cyano, and/or C
1
-C
6
-alkyl;
substituents having the designation “alkenyl” preferably denote C
6
-C
8
-alkenyl, which are optionally substituted by halogen (such as chlorine, bromine, or fluorine), hydroxyl, cyano, and/or C
1
-C
6
-alkyl, particularly allyl;
substituents having the meaning “hetaryl” preferably represent heterocyclic radicals having 5- to 7-membered rings, which preferably contain heteroatoms selected from the group consisting of N, S, and/or O and are optionally fused to aromatic rings or optionally carry further substituents (for example halogen, hydroxyl, cyano, and/or alkyl), the following being particularly preferred: pyridyl, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, quinolyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl, and
the substituents having the designation “aryl” preferably denote C
6
-C
10
-aryl (particularly phenyl or naphthyl), which are optionally substituted by halogen (such as F or Cl), hydroxyl, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, NO
2
, and/or CN.
Preferred Co-phthalocyanine complexes of the formula (I) are those in

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