Optical data store comprising an axially substituted cobalt...

Details Optical data store comprising an axially substituted cobalt... Optical data store comprising an axially substituted cobalt...

2002-03-20

2004-05-18

Mulvaney, Elizabeth (Department: 1774)

Stock material or miscellaneous articles

Circular sheet or circular blank

C428S064800, C430S270190, C430S270200

Reexamination Certificate

active

06737142

ABSTRACT:

The present invention relates to the use of an axially substituted cobalt phthalocyanine as light-absorbent compound in the light-writeable information layer of write-once optical data carriers, to optical data carriers and to a process for their production.
The write-once compact disk (CD-R) has recently experienced enormous volume growth. The light-absorbent compound of the information layer represents an important component of the optical data carrier and has to satisfy a variety of demanding requirements. The preparation of such compounds is not infrequently correspondingly costly (cf. WO-A-00/09522).
It is therefore an object of the invention to provide a simple-to-synthesize phthalocyanine dye which meets the demanding requirements (e.g. light stability, good signal
oise ratio, high writing sensitivity, damage-free application to the substrate material, etc.) for use as light-absorbent compound in the information layer of a write-once optical data carrier (especially a CD-R).
It has surprisingly been found that axially substituted cobalt phthalocyanines are very useful for this purpose.
The present invention accordingly provides an optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and if desired a protective layer or a further substrate or a covering layer have been applied, which can be written on and read by means of infrared light, preferably laser light, particularly preferably light having a wavelength in the range 750-800 nm, in particular 770-790 nm, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one cobalt(III) phthalocyanine in which the Co metal centre bears two axial substituents R
1
and R
2
which represent, independently of one another, CN, SCN, alkoxy or alkylthio is used as light-absorbent compound.
As light-absorbent compound, preference is given to using a cobalt phthalocyanine of the formula (I)
where
CoPc represents cobalt(III) phthalocyanine, where R
1
and R
2
are axial radicals of the cobalt and the radicals R
3
to R
6
correspond to substituents of the phthalocyanine, where
R
1
and R
2
represent, independently of one another, CN, SCN, alkoxy or alkylthio,
R
3
, R
4
, R
5
and R
6
represent, independently of one another, 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,
B is a bridge member selected from the group consisting of a direct bond, CH
2
, CO, CH(alkyl), C(alkyl)
2
, NH, S, O or —CH═CH—, where (B)
m
is a chemically realistic sequence of bridge members B and m=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 metallocenyl carbonyl radical in which the metal centre can be titanium, manganese, iron, ruthenium or osmium,
X
1
and X
2
represent, independently of one another, NR′R″, OR″ or SR″,
Y
1
represents NR′, O or S, Y
2
represents NR′,
n represents a number from 1 to 10 and
R′ and R″ represent, independently of one another, hydrogen, alkyl, cycloalkyl, aryl or hetaryl or form a direct bond or a bridge to one of the carbon atoms of the
w, x, y and z represent, independently of one another, numbers from 0 to 4 and w+x+y+z≦12,
R
7
and R
8
represent, independently of one another, alkylamino, hydroxyalkylamino, dialkylamino, bishydroxyalkylamino or arylamino or R
7
and R
8
together with the N atom to which they are bound form a heterocyclic 5-, 6- or 7-membered ring, with or without participation of further heteroatoms, in particular from the group consisting of O, N and S, where NR
7
R
8
represents, in particular, pyrrolidino, piperidino or morpholino,
R
12
represents alkyl, aryl, hetaryl or hydrogen,
Kat
+
represents a cation, in particular an alkali metal cation, ammonium cation, trialkylammonium cation, trialkyloxonium cation, triphenylcarbonium cation, diphenyliodonium cation, N-alkyl-pyridinium cation or a metallocenium cation, where the metal centre can be titanium, manganese, iron, ruthenium or osmium.
The alkyl, alkoxy, aryl and heterocyclic radicals may, if desired, bear further radicals such as alkyl, halogen, hydroxy, 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 partially halogenated or perhalogenated, the alkyl and alkoxy radicals may be ethoxylated or propoxylated or silylated. Adjacent alkyl and/or alkoxy radicals on aryl or heterocyclic radicals may together form a three- or four-membered bridge.
Preference is given to compounds of the formula (I) in which, for the radicals R
1
to R
8
and R, R′, R″ and R
12
:
Alkyl substituents are preferably C
1
-C
16
-alkyl, in particular C
1
-C
6
-alkyl, which may be unsubstituted or substituted by halogen such as chlorine, bromine or fluorine, hydroxy, cyano and/or C
1
-C
6
-alkoxy;
Alkoxy substituents are preferably C
1
-C
16
-alkoxy, in particular C
1
-C
6
-alkoxy which may be unsubstituted or substituted by halogen such as chlorine, bromine or fluorine, hydroxy, cyano and/or C
1
-C
6
-alkyl;
Cycloalkyl substituents are preferably C
4
-C
8
-cycloalkyl, in particular C
5
-C
6
-cycloalkyl, which may be unsubstituted or substituted by halogen such as chlorine, bromine or fluorine, hydroxy, cyano and/or C
1
-C
6
-alkyl;
Alkenyl substituents are preferably C
6
-C
8
-alkenyl, which may be unsubstituted or substituted by halogen such as chlorine, bromine or fluorine, hydroxy, cyano and/or C
1
-C
6
-alkyl, where alkenyl is particularly preferably allyl;
Hetaryl substituents are preferably heterocyclic radicals having 5- to 7-membered rings which preferably contain heteroatoms from the group consisting of N, S and/or O and may be fused to aromatic rings or may bear further substituents, for example halogen, hydroxy, cyano and/or alkyl, with particular preference being given to: pyridyl, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, quinolyl, benzoxazolyl, benzothiazolyl and benzimidazolyl;
Aryl substituents are preferably C
6
-C
10
-aryl, in particular phenyl or naphthyl, which may be unsubstituted or substituted by halogen such as F or Cl, hydroxy, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, NO
2
and/or CN.
Preference is given to cobalt phthalocyanines of the formula (I) in which
R
3
, R
4
, R
5
and R
6
represent, independently of one another, chlorine, fluorine, bromine, iodine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, tert-amyl, hydroxyethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl, phenyl, p-tert-butylphenyl, p-methoxyphenyl, isopropylphenyl, trifluoromethylphenyl, naphthyl, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, tert-butylamino, pentylamino, tert-amylamino, benzylamino, methylphenylhexylamino, hydroxyethylamino, aminopropylamino, aminoethylamino, 3-dimethylaminopropylamino, 3-diethylaminopropylamino, diethylaminoethylamino, dibutylaminopropylamino, morpholinopropylamino, piperidinopropylamino, pyrrolidinopropylamino, pyrrolidonopropylamino, 3-(methyl-hydroxyethylamino)propylamino, methoxyethylamino, ethoxyethylamino, methoxypropyl-amino, ethoxypropylamino, methoxyethoxypropylamino, 3-(2-ethylhexyloxy)propylamino, isopropyloxypropylamino, dimethylamino, diethylamino, diethanolamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, di-tert-butylamino, dipentylamino, di-tert-amylamino, bis(2-ethylhexyl)amino, bis(aminopropyl)amino, bis(aminoethyl)amino, bis(3-dimethylaminopropyl)amino, bis(3-diethylaminopropyl)amino, bis(diethylaminoethyl

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