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Hydrazine Compound and Silver Halide Photographic Material Containing the Same

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Hydrazine Compound and Silver Halide Photographic Material Containing the Same Europaisches Patentamt J European Patent Office © Publication number: 0 652 470 A1 Office europeen des brevets © EUROPEAN PATENT APPLICATION © Application number: 94117693.5 © Int. CI.6: G03C 1/06, C07D 257/04, C07D 487/04 @ Date of filing: 09.11.94 © Priority: 10.11.93 JP 303307/93 © Applicant: FUJI PHOTO FILM CO., LTD. 210 Nakanuma @ Date of publication of application: Minami-Ashigara-shi 10.05.95 Bulletin 95/19 Kanagawa 250-01 (JP) © Designated Contracting States: @ Inventor: Hioki, Takanori, c/o Fuji Photo Film BE DE FR GB IT NL Co.,Ltd. 210, Nakanuma Minami Ashigara-shi, Kanagawa (JP) Inventor: Ikeda, Tadashi, c/o Fuji Photo Film Co.,Ltd. 210, Nakanuma Minami Ashigara-shi, Kanagawa (JP) © Representative: Patentanwalte Grunecker, Kinkeldey, Stockmair & Partner Maximilianstrasse 58 D-80538 Munchen (DE) © Hydrazine compound and silver halide photographic material containing the same. © A silver halide photographic material comprising a support having thereon a silver halide emulsion layer which comprises a hydrazine compound having at least one absorbent group to silver halide, wherein two nitrogen atoms of the hydrazine compound are substituted by four substituents and the carbon atoms in the four substituents bonded directly to the two nitrogen atoms are not substituted by an oxo group. CM m CO Rank Xerox (UK) Business Services (3. 10/3.09/3.3.4) EP 0 652 470 A1 FIELD OF THE INVENTION The present invention relates to a silver halide photographic material having a high sensitivity and an excellent storage stability. 5 The present invention also relates to a novel compound. BACKGROUND OF THE INVENTION Silver halide photographic materials have hitherto been demanded to have a high sensitivity. In io particular, spectrally sensitized silver halide photographic materials have keenly demanded to have a high sensitivity. The spectral sensitization is a very important and essential technique in the production of a light- sensitive material having a high sensitivity and an excellent color reproducibility. The spectral sensitizer has a function to absorb light in a long wavelength region where the silver halide photographic emulsion 75 inherently does not absorb light in a substantial sense and to transmit the light absorption energy to the silver halide. The increased amount of light captured by the spectral sensitizer is advantageous to enhance the photographic sensitivity. Accordingly, it has been attempted to increase the captured light amount by increasing the amount of the spectral sensitizer added to a silver halide emulsion. However, if the spectral sensitizer is added to a silver halide emulsion in an amount exceeding the optimum range, the sensitivity is, 20 on the contrary, greatly reduced. This is generally called as dye desensitization and is a phenomenon that desensitization occurs in the region to which the silver halide is inherently light-sensitive and where the sensitizing dye absorbs substantially no light. If the dye desensitization is large, the spectral sensitization effect may be provided but overall sensitivity is reduced. In other words, with the reduction in dye desensitization, the sensitivity in the region where the sensitizing dye absorbs light (namely, spectral 25 sensitivity) increases correspondingly. Therefore, the improvement in dye desensitization is a great subject in the spectral sensitization technique. The dye desensitization is larger as the sensitizing dye has its light- sensitive region at a longer wavelength. This is described in T.H. James, The Theory of the Photographic Process, pp. 265-268 (Macmillan, 1966). Further, as described in T. Tani et al, Journal of the Physical Chemistry, Vol. 94, p. 1298 (1990), 30 sensitizing dyes having a reduction potential more noble than -1 .25 V are known to provide a low relative quantum yield in spectral sensitization. In order to increase the relative quantum yield of such a dye in spectral sensitization, super-sensitization by capturing positive holes has been proposed as described in the above-described The Theory of the Photographic Process, pp. 259-265 (1966). In order to solve the above-described desensitization, JP-A-5-216152 (the term "JP-A" as used herein 35 means an "unexamined published Japanese patent application") describes hydrazine compounds having a specific structure. However, still higher sensitivity and more improved storage stability have been demanded. SUMMARY OF THE INVENTION 40 An object of the present invention is to provide a highly sensitive silver halide photographic material. Another object is to provide a silver halide photographic material having a high storage stability. Further object is to provide a novel compound. The above-described objects of the present invention have been achieved by a silver halide photo- 45 graphic material comprising at least one hydrazine compound having at least one adsorption group to silver halide, more preferably at least one compound represented by the following formula (I) (Het-hn— HQKa (Hy)]k3 (I) 50 wherein Het represents a group having a 5-, 6- or 7-membered heterocyclic ring which contains at least one nitrogen atom and may contain a hetero atom other than a nitrogen atom, Q represents a divalent linking group composed of an atom or an atomic group containing at least one of a carbon atom, a nitrogen atom, a sulfur atom and an oxygen atom, Hy represents an atomic group having a hydrazine structure 55 represented by formula (II), k1 and k3 each represents 1, 2, 3 or 4, and k2 represents 0 or 1, 2 EP 0 652 470 A1 Ri^ /R^3 N— (II) R2 R4 5 wherein Ri , R2, R3 and R+ each represents an alkyl group, an aryl group or a heterocyclic group, with the proviso that the carbon atom bonded directly to the nitrogen atom of hydrazine represented by Hy is not substituted by an oxo group. The above-described objects have been achieved by the compound represented by formula (I) above. io More preferably, these have been achieved by a spectrally sensitized silver halide photographic material containing a hydrazine compound represented by formula (I). DETAILED DESCRIPTION OF THE INVENTION 15 The present invention will be described below in more detail. As the adsorption group to silver halide, preferred is a group having the following partial structure, and having a 5-, 6- or 7-membered heterocyclic ring which contains at least one nitrogen atom and may contain a hetero atom other than a nitrogen atom (e.g., oxygen, sulfur, selenium, tellurium). 20 O N O N H 25 H 30 5^N' H 35 ,-Z'-% ■N- R H 40 wherein Z represents an atomic group necessary for forming a nitrogen-containing heterocyclic ring, and R represents an aliphatic group. The hydrazine structure represented by formula (II), which is used preferably as Hy, will be described in detail. 45 In the formula, R1 , R2, R3 and R+ each represents an alkyl group, an aryl group or a heterocyclic group. R1 and R2, R3 and R+, R1 and R3, or R2 and R+ may combine with each other to form a ring but do not form an aromatic ring. In R1 , R2, R3 and R+, the carbon atom directly bonded to the nitrogen atom of hydrazine is not substituted by an oxo group. 50 The hydrazine compound represented by formula (II) is substituted by at least one -(Q)k2-(Het)k1. The compound represented by formula (II) is particularly preferably a compound selected from those represented by formulae (III), (IV) and (V) for achieving high sensitivity. 55 3 EP 0 652 470 A1 R5^ A — N R7 /Li 10 -iz- 15 / ]f (V) 20 In the formulae, R5, Rg, R7 and Rs each represents an alkyl group, an aryl group or a heterocyclic group. Z1 represents an alkylene group having 4 or 6 carbon atoms. Z2 represents an alkylene group having 2 carbon atoms. Z3 represents an alkylene group having 1 or 2 carbon atoms. 25 Z4 and Z5 each represents an alkylene group having 3 carbon atoms. Li and L2 each represents a methine group. In R5, Rg, R7, Rs, Z1 , Z+ and Z5, the carbon atom directly bonded to the nitrogen atom of hydrazine is not substituted by an oxo group. The compounds of formulae (III), (IV) and (V) are each substituted by at least one -(Q)k2-(Het)k1. 30 The compounds represented by formula (III) and (IV) are more preferred and the compound repre- sented by formula (III) is particularly preferred. Formula (II) will be described below in detail. R1 , R2, R3 and R+ each preferably represents an unsubstituted alkyl group (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, octyl, dodecyl, octadecyl, cyclopentyl, cyclopropyl, cyclohexyl); a substi- 35 tuted alkyl group {when the substituent is expressed by V, the substituent represented by V is not particularly limited; examples thereof include a carboxyl group, a sulfo group, a cyano group, a halogen atom (e.g., fluorine, chlorine, bromine, iodine), a hydroxyl group, an alkoxycarbonyl group (e.g., methoxycar- bonyl, ethoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl), an alkoxy group (e.g., methoxy, ethoxy, benzyloxy, phenethyloxy), an aryloxy group having 18 or less carbon atoms (e.g., phenoxy, 4-methyl- 40 phenoxy, a-naphthoxy), an acyloxy group (e.g., acetyloxy, propionyloxy), an acyl group (e.g., acetyl, propionyl, benzoyl, mesyl), a carbamoyl group (e.g., carbamoyl, N,N-dimethylcarbamoyl, morpholinocar- bonyl, piperidinocarbonyl), a sulfamoyl group (e.g., sulfamoyl, N,N-dimethylsulfamoyl, morpholinosulfonyl, piperidinosulfonyl), an aryl group (e.g., phenyl, 4-chlorophenyl, 4-methylphenyl, a-naphthyl), a heterocyclic group (e.g., 2-pyridyl, tetrahydrofurfuryl, morpholino, 2-thienyl), an amino group (e.g., amino, dimethylamino, 45 anilino, diphenylamino),
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