Cyanine dye

Details Cyanine dye Cyanine dye

2001-11-05

2003-11-18

Letscher, Geraldine (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Silver compound sensitizer containing

C430S570000, C430S577000, C430S581000, C430S583000, C430S585000, C430S567000

Reexamination Certificate

active

06649335

ABSTRACT:

This invention relates to new heterocyclic compounds, particularly spectral sensitisers of the cyanine dye type, and to intermediates for the synthesis thereof. The invention also relates to photographic silver halide materials which contain these new compounds.
It is known that cyanine dyes can be used for the spectral sensitisation of silver halide emulsions. Various measures have been disclosed in order to achieve a further increase in speed, such as special substituted cyanine dyes in U.S. Pat. No. 5,674,674 and a combination of two trimethine cyanines in EP 608 955, for example. In order to reduce fogging, anti-fogging agents are known, for example, which often comprise mercapto-substituted heterocycles. Cyanine dyes which result in a low degree of fogging are described in U.S. Pat. No. 5,415,980.
With these known spectral sensitisers, however, no success has been achieved in producing photographic materials of very high speed which are simultaneously distinguished by a low degree of fogging. Using these known measures, an increase in speed is usually accompanied by an increase in fogging, and measures for reducing fogging generally result in a loss of speed. Moreover, at the large amounts which are necessary for high speeds, the known sensitisers often result in unwanted staining of the processed materials due to spectral sensitisers which have not been removed by washing (sensitiser staining). However, in order to fulfil the ever-increasing demands as regards image quality which are imposed even on high-speed photographic materials a very high speed/fogging ratio and a low degree of sensitiser staining are indispensable.
The underlying object of the present invention is thus to provide new spectral sensitisers, the use of which results in photographic materials which are distinguished by very high speed, low fogging and a low degree of sensitiser staining.
Surprisingly, it has now been found that is achieved if new spectral sensitisers are used, of the type comprising cyanine or merocyanine dyes, which at one end of their methine chain comprise a heterocycle derived from indole with a condensed-on furan ring.
The present invention therefore relates to a heterocyclic compound corresponding to formula (I)
wherein
X
1
denotes C(R
5
, R
6
), NR
7
, O, S or Se,
Y
1
denotes N or N
(+)
—R
8
,
A
1
denotes H or an organic radical,
at least one of the combinations R
1
with R
2
, R
2
with R
3
or R
3
with R
4
denote the remaining members for the completion of a substituted or unsubstituted condensed furanoring system, and the R
1
to R
4
radicals, which are not part of the furan ring system, independently of each other denote H, a halogen, SH, CN, CF
3
, alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio,
R
5
to R
7
denote alkyl, alkylene-SO
3
Z
1
or alkylene-CO
2
Z
1
, wherein the alkyl and alkylene can be can be further substituted and each comprise 1 to 6 C atoms, particularly 1 to 4 C atoms,
R
8
denotes alkyl, alkylene-SO
3
Z
1
, alkylene-CO
2
Z
1
or alkylene-Y
2
—N(Z
1
)—Y
3
-alkyl, wherein alkyl and alkylene can be further substituted and each comprise 1 to 6 C atoms,
Z
1
denotes H or a negative charge,
Y
2,
Y
3
, independently of each other, denote —S(═O)
2
— or —C(═O)—, and
M
1
denotes a counterion which may be necessary for charge equalisation,
wherein R
1
with R
2
or R
3
with R
4
, provided that they are not part of the furan ring system, can also each jointly denote the remaining members for the completion of a substituted or unsubstituted condensed-on benzene or naphthalene ring system, and wherein Y
1
has the meaning N
(+)
—R
8
if A
1
denotes the remaining members of a cyanine dye.
The oxygen of the furan ring can assume any of the three free positions, but is preferably bonded directly to the benzene nucleus of formula (I).
The two hydrogen atoms of the furan ring system can, independently of each other, be substituted by a halogen, CN, CF
3
, an alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio or can jointly be substituted by the remaining members for the completion of a substituted or unsubstituted condensed-on benzene or naphthalene ring system. The furan ring system is preferably unsubstituted.
The alkyl, alkenyl and alkylene groups in the sense of the present invention can be straight chain, branched or cyclic.
The alkyl, alkenyl, alkylene, aryl and heterocyclyl groups can be substituted, for example, by alkyl, alkenyl, alkyne, alkylene, aryl, heterocyclyl, hydroxy, carboxy, halogen, alkoxy, aryloxy, heterocyclyloxy, alkylthio, arylthio, heterocyclylthio, alkylseleno, arylseleno, heterocyclylseleno, acyl, acyloxy, acylamino, cyano, nitro, amino, thio or mercapto groups,
wherein a heterocyclyl represents a saturated, unsaturated or aromatic heterocyclic radical and an acyl represents the radical of an aliphatic, olefinic or aromatic carboxylic, carbamic, carbonic, sulphonic, amidosulphonic, phosphoric, phosphonic, phosphorous, phosphinic or sulphinic acid.
Compounds of formula (I) are preferred in which
A
1
denotes H, alkyl, alkenyl or the remaining members of a cyanine or mero-cyanine dye, and
only one of the combinations R
1
with R
2
, R
2
with R
3
or R
3
with R
4
denotes the remaining members for the completion of a substituted or unsubstituted condensed-on furan ring system.
In one preferred embodiment of the invention, the new compounds are cyanine dyes of formula (II)
wherein
X
2
denotes O, S, Se or NR
13
,
R
2
with R
3
, or R
3
with R
4
, each jointly denote the remaining members for the completion of a substituted or unsubstituted condensed furanoring system, and the R
2
or R
4
radical, which is not part of the furan ring system, denotes H, a halogen, SH, CN, CF
3
, alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio,
R
10
to R
12
, independently of each other, denote H, a halogen, SH, CN, CF
3
, alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio, or
R
10
with R
11
, or R
11
with R
12
, each jointly denote the remaining members for the completion of a substituted or unsubstituted condensed furano, benzene or naphthalene ring system, and the R
10
or R
12
radical, which is not part of the ring system, denotes H, a halogen, SH, CN, CF
3
, alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio,
R
9
denotes alkyl, alkylene-SO
3
Z
1
, alkylene-CO
2
Z
1
or alkylene-Y
2
—N(Z
1
)—Y
3
-alkyl, wherein the alkyl and alkylene can be further substituted and each comprise 1 to 6 C atoms,
R
13
denotes alkyl, alkylene-SO
3
Z
1
or alkylene-CO
2
Z
1
, wherein the alkyl and alkylene can be further substituted and each comprise 1 to 6 C atoms,
L
1
, L
2
, L
3
denote a substituted or unsubstituted methine group, which can be a constituent of one or more carbocyclic rings,
n denotes 0, 1, 2 or 3, particularly 0, 1 or 2, and
wherein the other substituents have the meanings given above.
Of the possible variants, sensitisers comprising an arrangement of the furan ring system corresponding to formulae (III) or (IV) are particularly advantageous
wherein
R
14
, R
15
independently of each other, denote H, a halogen, CN, CF
3
, alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio, and wherein the other substituents have the meanings given above. It is preferable if R
14
and/or R
15
, particularly R
14
and R
15
, denote H.
Particularly high speeds can be obtained using a cyanine dye according to formula (II), and particularly according to formulae (III) and (IV), in which
X
1
denotes S or Se, and
R
10
to R
12
independently of each other, denote H, a halogen, CN, CF
3
, alkyl, phenyl, aryl, heterocyclyl, alkoxy, aryloxy, alkylthio or arylthio, wherein R
10
with R
11
or R
11
with R
12
can each jointly denote the remaining members for the completion of a substituted or unsubstituted condensed benzene or naphthalene ring system.
The new compounds of formula (V)
wherein
A
2
denotes H, alkenyl or alkyl,
and wherein the other substituents have the meanings given above, can be used for

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