JP2808364B2 - Image forming method and silver halide photographic material - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an image forming method using a silver halide photographic light-sensitive material, and more particularly to an image formation method in which a hydrazine compound is contained in a silver halide photographic light-sensitive material to obtain a high contrast photographic image. About the method.

[0002]

BACKGROUND OF THE INVENTION The photomechanical process includes the step of converting a continuous tone original into a halftone image. In this step, a technique based on infectious development has been used as a technique capable of reproducing a super-high contrast image.

The lithographic silver halide photographic light-sensitive material used for infectious development has, for example, an average particle diameter of 0.2 μm, a narrow particle distribution, a uniform particle shape, and a high silver chloride content (at least 50 mol. % Or more) It consists of a silver chlorobromide emulsion.
By processing this lithographic silver halide photographic material with an alkaline hydroquinone developer having a low sulfite ion concentration, a so-called lithographic developer, a high contrast,
An image with high sharpness and high resolution can be obtained.

However, since these squirrel-type developers are susceptible to air oxidation, they have extremely poor preservative properties.
Even during continuous use, it is difficult to keep development quality constant.

There is known a method for obtaining a high-contrast image quickly without using the lithographic developer. For example, as disclosed in JP-A-56-106244, a hydrazine derivative is contained in a silver halide photosensitive material. According to these methods, a high-contrast image can be obtained by processing with a developer having good preservation properties and capable of rapid processing.

[0006] In these techniques, the hydrazine derivative must be processed with a developer having a pH of 11.0 or more in order to sufficiently exhibit high contrast. pH 11.0 or higher
In the pH developer, the developing agent is easily oxidized when exposed to air.
Although it is more stable than the squirrel developing solution, an ultra-high contrast image is often not obtained due to oxidation of the developing agent. To compensate for this disadvantage, Japanese Patent Application Laid-Open Nos. 63-29751 and 333,435 and 345,025 disclose relatively low specifications.
There is disclosed a silver halide photographic light-sensitive material containing a high-contrast agent which makes high-contrast even in a pH developer.

However, when the above-mentioned high contrast agent is used, pH 11.
The present inventors have found that although the developer becomes harder even with a developer less than 0, there is a problem that the light-sensitive material is desensitized with the passage of time and softens.

[0008]

SUMMARY OF THE INVENTION An object of the present invention is to provide a silver halide photographic light-sensitive material having high photographic characteristics even when processed with a developing solution having a pH of less than 11.0 and having good aging performance. .

[0009]

The object of the present invention is achieved by the following silver halide photographic material (1) or (2).

(1) At least one photosensitive silver halide emulsion layer and at least one antistatic layer are coated on a support, and the photosensitive silver halide emulsion layer and / or an adjacent layer thereof are provided. Image forming, wherein a silver halide photographic material containing at least one hydrazine derivative represented by the following general formula [A] or [B] in a layer is treated with a processing agent having a pH of less than 11.0. Method.

General formula [A] A-NHNH- COCO- N (R ₁ ) (R ₂ ) General formula [B] A-NHNH-COCO-O-R ₃ [where A is a sulfonamide group, an alkylamino Foundation
Or an ant optionally substituted with an alkylideneamino group
At least one sulfur or oxygen atom
Sulfonamide group, alkylamino group or alkyl
A heterocyclic group which may be substituted with a
And, R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, saturated or unsaturated, hydroxy group or an alkoxy group der
And at least one of R ₁ and R ₂ is an alkenyl group, an alkynyl group, a saturated heterocyclic group, a hydroxy group or an alkoxy group . R ₃ represents an alkynyl group or a saturated heterocyclic group.

The compound represented by the general formula [A] or [B] includes a compound in which at least one H of -NHNH- in the formula is substituted with a substituent. ]

Hereinafter, the present invention will be described in detail.

In the above general formula [A] or [B], A
Is an aryl group (eg, phenyl, naphthyl, etc.), or a heterocyclic group containing at least one sulfur atom or oxygen atom (eg, thiophene, furan, benzothiophene,
Pyran, etc.) and table, the aryl group and the heterocyclic ring
Honamido group, alkylamino group or alkylideneamido
And it may be substituted with an amino group.

R ₁ and R ₂ each represent a hydrogen atom, an alkyl group (eg, methyl, ethyl, methoxyethyl, cyanoethyl, hydroxyethyl, benzyl, trifluoroethyl, etc.) and an alkenyl group (eg, allyl, butenyl,
Pentenyl, pentadienyl, etc.), alkynyl groups (eg, propargyl, butynyl, pentynyl, etc.), aryl groups (eg, phenyl, naphthyl, cyanophenyl,
Methoxyphenyl etc.), a heterocyclic group (for example, pyridine,
Thiophene, unsaturated heterocyclic groups such as furan and saturated heterocyclic groups such as tetrahydrofuran and sulfolane), hydroxy group, alkoxy group (for example, methoxy, ethoxy,
Benzyloxy, cyanomethoxy, etc.), alkenyloxy group (eg, allyloxy, butenyloxy, etc.), alkynyloxy group (eg, propargyloxy, butynyloxy, etc.), aryloxy group (eg, phenoxy, naphthyloxy, etc.), or heterocyclic oxy group (e.g., pyridyloxy, pyrimidyloxy, etc.) to the table.

Specific examples of the alkynyl group and the saturated heterocyclic group represented by R ₃ include those described above.

[0017]

In each formula, A preferably contains at least one diffusion-resistant group or silver halide adsorption-promoting group. As the anti-diffusion group, a parast group commonly used in immobile photographic additives such as couplers is preferable. The ballast group is a group having a carbon number of 8 or more, which is relatively inert to photographic properties. For example, the ballast group is selected from an alkyl group, an alkoxy group, a phenyl group, an alkylphenyl group, a phenoxy group and an alkylphenoxy group. Can be.

Examples of the silver halide adsorption-promoting group include groups described in US Pat. No. 4,385,108 such as a thiourea group, a thiourethane group, a heterocyclic thioamide group, a mercapto heterocyclic group, and a triazole group.

In the general formulas [A] and [B], H of -NHNH-, that is, the hydrogen atom of hydrazine is a sulfonyl group (eg, methanesulfonyl, toluenesulfonyl, etc.), an acyl group (eg, acetyl, trifluoroacetyl, The compound represented by the general formulas [A] and [B] may be substituted with a substituent such as ethoxycarbonyl) or an oxalyl group (eg, ethoxylaryl, pyruvoyl, etc.).

[0021]

[0022] is generally Oite formula (A), R ₁ and R ₂ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a saturated or unsaturated heterocyclic group, hydroxy group, or an alkoxy group, Further, a compound in which at least one of R ₁ and R ₂ represents an alkenyl group, an alkynyl group, a saturated heterocyclic group, a hydroxy group, or an alkoxy group is more preferred.

Typical compounds represented by the above general formulas [A] and [B] include the following. However, needless to say, specific compounds of the general formulas [A] and [B] that can be used in the present invention are not limited to these compounds.

Specific examples of compounds

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The antistatic layer of the present invention is preferably made of a reaction product of a water-soluble conductive polymer, a hydrophobic latex and an epoxy-based curing agent, or a metal oxide.

The water-soluble conductive polymer of the present invention includes a polymer having at least one conductive group selected from a sulfonic acid group, a sulfate group, a quaternary ammonium salt, a tertiary ammonium salt and a carboxyl group. . The conductive groups require at least 5% by weight per polymer molecule. The water-soluble conductive polymer may contain a hydroxy group, an amino group, an epoxy group, an aziridine group, an active methylene group, a sulfinic acid group, an aldehyde group, and a vinyl sulfone group.

The molecular weight of the polymer is from 3000 to 100,000, preferably from 3500 to 50,000.

The following are examples of compounds of the water-soluble conductive polymer used in the present invention, but the compounds are not limited thereto.

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In the above A-1 to A-21, Mn represents an average molecular weight (the average molecular weight is a number average molecular weight in the present specification) and is expressed in terms of polyethylene glycol.
It is based on the value measured by GPC.

The hydrophobic polymer particles contained in the water-soluble conductive polymer layer of the present invention are composed of a so-called latex that is substantially insoluble in water. The hydrophobic polymer is obtained by polymerizing a monomer selected in any combination from styrene, a styrene derivative, an alkyl acrylate, an alkyl methacrylate, an olefin derivative, a halogenated ethylene derivative, a vinyl ester derivative, and acrylonitrile. In particular, at least styrene derivatives, alkyl acrylates and alkyl methacrylates
It is preferably contained at 30 mol%. In particular, 50 mol% or more is preferable.

The following are specific examples of the latex of the present invention.

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Next, the epoxy-based curing agent in the present invention is not particularly limited as long as it has an epoxy group, and can be used in combination with a plurality of curing agents, for example, aldehyde-based and vinylsulfone-based curing agents.

Preferred epoxy compounds are those containing a hydroxy group or an ether condensation. In the present invention, the epoxy equivalent is a value represented by the following formula.

Epoxy equivalent = molecular weight / the number of epoxy groups in one molecule This value is, for example, New Experimental Chemistry Course 13 (1) Organic Structure P58
Other color quantification is possible by the method of (Maruzen).

The epoxy equivalent is preferably from 50 to 300, more preferably from 80 to 210. If it is more than 300, the curing is weak, and if the amount is increased, the coating property deteriorates. If the curing is weak, scratches are likely to occur. When the epoxy equivalent is less than 50, the curing is strong, but the haze and the residual color are deteriorated, and even if the amount is reduced, it does not improve.

Specific examples of the epoxy compound of the present invention will be given. The numbers in parentheses indicate epoxy equivalents.

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The addition amount of the epoxy curing agent is 5 mg / m ^{2 to 1} g / m
² is preferred.

The addition position is the antistatic layer,
It can be used in combination with any of the emulsion layer, the backing layer and the protective layer. Further, it is more preferable to add it together with the hydrophilic colloid layer on the side having the antistatic layer from the viewpoint of improving film formation.

Next, as the metal oxide in the case where the antistatic layer is made of a metal oxide, any of indium oxide, tin oxide, metal oxide doped with antimony atoms, or a combination thereof can be used.

As the indium oxide, there are known indium oxide (In ₂ O) and indium oxide (In ₂ O ₃ ). In the present invention, it is preferable to use indium oxide. .

Further, as tin oxide, stannous oxide (Sn
O) and stannic oxide (SnO ₂ ) are known, but stannic oxide is preferably used in the present invention.

Specific examples of metal oxides doped with antimony atoms include tin oxide and iridium oxide. To dope the metal oxide with antimony, a tin or indium halide, an alkoxylate or a nitrate compound and an antimony halide or a nitrate compound and an antimony halide, an alkoxylate or a nitrate chloride are mixed and oxidized and calcined. Can be obtained. These metal compounds can be easily obtained from metal compound manufacturers such as Japan Yttrium Corporation. The content of antimony is preferably 0.5 to 10% by weight based on tin or indium. It is preferable to add these inorganic compounds by dispersing them in a hydrophilic colloid such as gelatin or dispersing them in a polymer compound such as acrylic acid or maleic acid. The loading ratio per binder is preferably from 1 to 100% by weight.

The film surface pH of the antistatic layer of the present invention is 8.
0 or less is preferred, but too low is not preferred due to the stability of the film. Particularly preferably, it is 3.0 to 7.5.

The antistatic layer of the present invention may be on the support side of the photosensitive layer, or may be on the opposite side of the support with respect to the photosensitive layer, that is, on the back side.

In the present invention, an antistatic layer is provided on a transparent support. The transparent support can be used for all photographic purposes, but is preferably polyethylene terephthalate or cellulose triacetate made to transmit at least 90% of visible light.

These transparent supports are prepared by a method well known to those skilled in the art. In some cases, a slight amount of a dye is added so as not to substantially impede light transmission, and the transparent support may be tinted. You may.

The support of the present invention may be provided with an undercoat layer containing a latex polymer after the corona discharge treatment. Corona discharge treatment has an energy value of 1 mW
１1 KW / (m ² · min) is particularly preferably applied. It is particularly preferable to perform the corona discharge treatment again after the application of the latex subbing layer and before the application of the antistatic layer.

In the development processing of the silver halide photographic material of the present invention, for example, the following developing agents are used. HO
-(CH = CH) n-OH type developing agents are typically
There are hydroquinone, and catechol, pyrogallol and the like.

As the HO- (CH ＝ CH) n-NH ₂ type developer, ortho- and para-aminophenols or aminopyrazolones are typical, and N-methyl-p-aminophenol, N-β -Hydroxyethyl-p-aminophenol, p-
There are hydroxyphenylaminoacetic acid, 2-aminonaphthol and the like.

As the heterocyclic developer, 1-phenyl-3
-Pyrazolidone, 1-phenyl-4,4-dimethyl-3-pyrazolidone, 1-phenyl-4-methyl-4-hydroxymethyl-3-pyrazolidone, 1-phenyl-4-methyl-4-hydroxymethyl-3
-Pyrazolidones such as 3-pyrazolidones.

In addition, TH James, The Theory of the Photographic Process, 4th Edition (The
Theory of the Photographic Process, Fourth Editio
n) Pages 291-334 and the Journal of the American Chemical Society
Chemical Society), vol. 73, p. 3, 100 (1951), is a developer that can be effectively used in the present invention.

These developers may be used alone or in combination of two or more, but it is preferable to use two or more in combination.

The effect of the present invention is not impaired even if a sulfite such as sodium sulfite or potassium sulfite is used as a preservative in the developer used for developing the light-sensitive material of the present invention. Further, hydroxylamine and hydrazide compounds may be used as preservatives. In addition, it can have a pH adjustment and a buffer function with caustic alkali, alkali carbonate, amine or the like used in a general black and white developer.

The developer used in the present invention is characterized in that a developer having a pH of less than 11 can be used. Further, the developer may be an inorganic development inhibitor such as bromkari and an organic development inhibitor such as 5-methylbenzotriazole, 5-methylbenzimidazole, 5-nitroindazole, adenine, guanine, 1-phenyl-5-mercaptotetrazole, ethylenediamine. Metal ion scavengers such as tetraacetic acid, methanol, ethanol, benzyl alcohol, development accelerators such as polyalkylene oxide, sodium alkylaryl sulfonate,
It is optional to add surfactants such as natural saponins, sugars or alkyl esters of the above compounds, hardeners such as glutaraldehyde, formalin, glyoxal, etc., and ionic strength modifiers such as sodium sulfate.

The developing solution used in the present invention includes alkanolamines such as diethanolamine and triethanolamine, diethylene glycol, and the like as organic solvents.
Glycols such as triethylene glycol may be contained. Also, diethylamino-1,2-propanediol,
Alkylamino alcohols such as butylaminopropanol can be particularly preferably used.

[0109]

EXAMPLES Specific examples of the present invention will be described below, but the embodiments of the present invention are not limited to these examples.

(Preparation of Silver Halide Photographic Emulsion A) A silver iodobromide emulsion (2 mol% of silver iodide per mol of silver) was prepared by a double jet method. During this mixing, K ₂ IrCl ₆ was added to silver 1
8 × 10 ^-7 mol was added per mol. The resulting emulsion was an emulsion composed of cubic monodisperse grains having an average grain size of 0.24 μm (coefficient of variation: 9%). 6.5 ml of silver per mole of this emulsion
After adding a 1% aqueous solution of potassium iodide, denatured gelatin (Exemplary compound G-8 of Japanese Patent Application No. 1-180787) was added, followed by washing with water in the same manner as in Example 1 of Japanese Patent Application No. 1-180787. , Desalted. The pAg at 40 ° C. after desalting was 8.0.

Further, the following compound as an antibacterial agent upon redispersion
A mixture of [A], [B] and [C] was added.

Compound [A] + [B] + [C]

[0113]

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(Application of Antistatic Layer) (P) Application of Polymer Antistatic Layer (P-1 to P-5) Polyethylene terephthalate was coated on both sides undercoat in the same manner as described in Example 1 of JP-A-59-19941. Then, antistatic layers P-1 to P-5 having the following composition were applied to one surface thereof (Table 1).

Water-soluble conductive polymer 2.5 g / m^Two  1.7 g / m hydrophobic latex^Two  Ammonium sulfate 20mg / m^Two  Hardener 100mg / m^Two  Polyethylene glycol 5mg / m^Two  (M) Metal oxide antistatic layer Metal oxide having the following composition in the same manner as the polymer antistatic layer
An antistatic layer M was applied.

Gelatin 0.2 g / m^Two  Styrene-maleic acid copolymer 50mg / m^Two  Polyethylene glycol 2mg / m^Two  Tin oxide 0.2mg / m^Two  Glyoxal hardener 10mg / m^Two

[0117]

[Table 1]

(Preparation of Silver Halide Photosensitive Material) After a corona discharge was applied to the undercoat layer of the support provided with the antistatic layer on the side opposite to the antistatic layer, a silver halide having the following formula (1) gelatin amount 2.0 g / m ² and the emulsion layer, the silver amount of 3.2 g /
m ^2, and an emulsion protective layer of the following formula (2) is further coated thereon so that the amount of gelatin becomes 1.0 g / m ² ,
Next, after performing corona discharge on the antistatic layer, a backing layer is coated according to the following formula (3) so that the gelatin becomes 2.4 g / m ^2, and a backing protective layer having the following formula (4) is further formed thereon. Was applied so that the amount of gelatin became 1 g / m ² to obtain Sample Nos. 1 to 10.

Formulation (1) (Silver halide emulsion layer composition) Gelatin 2.0 g / m^Two  Silver halide emulsion A Silver amount 3.2
g / m²  Sensitizing dye:

[0120]

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Stabilizer: 4-methyl-6-hydroxy-1,3,3a, 7-tetrazaindene 30 mg / m^Two  Antifoggant: Adenine 10mg / m^Two  Surfactant: saponin 0.1g / m^Two

[0122]

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Hydrazine derivatives according to the present invention The nucleation accelerators shown in Table 2 are:

[0124]

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Latex polymer:

[0126]

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Polyethylene glycol molecular weight 4000 0.1 g / m^Two  Hardener H-1 60mg / m^Two

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Formulation (2) (Emulsion protective layer composition) Gelatin 0.9 g
/ M²  Surfactant: S-2

[0130]

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Surfactant: S-3

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Matting agent: silica having an average particle size of 3.5 μm 3 mg / m^Two  Hardener: Formalin 30mg / m^Two  Formulation (3) (backing layer composition)

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[0135] Gelatin
 2.4g / m^Two  Surfactant: saponin 0.1g / m^Two  : S-1 6mg / m^Two  Hardener:

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Formulation (4) (Backing protective layer composition) Gelatin 1 g / m^Two  Matting agent: Polymethyl methacrylate with an average particle size of 3.0 to 5.0 μm 15 mg / m^Two  Surfactant: S-2 10mg / m^Two  Hardener: Glyoxal 25mg / m²  : H-1 35mg / m^Two  The obtained sample was split in half, and one was cut at 23 ° C and 55% RH for 3 hours.
Saved for days. The other one is a test for the age of 50
Both samples stored for 3 days at 55 ° C and 55% RH were combined with a step wedge.
And exposed to 3200K tungsten light for 5 seconds
After that, the developer and the fixing solution having the compositions shown in Table 2 below were charged and the
Processing was performed under the following conditions using an automatic developing machine for high-speed processing.

Developer Formulation Developer 1 Developer 2 Sodium ethylenediaminetetraacetate 1 g 1 g Sodium sulfite 60 g 60 g Trisodium phosphate (12 hydrate) 75 g-boric acid-40 g Hydroquinone 22.5 g 35 g Sodium hydroxide 8 g 8 g Sodium bromide 3g 3g 5-methylbenzotriazole 0.25g 0.2g 1-phenyl-5-mercaptotetrazole 0.08g 0.08g 1-phenyl-4,4-dimethyl-3-pyrazolidone-0.2g methol 0.25g-phenyltylpicolinium bromide-2.5 g Add water and adjust pH with 1 l 1 l sodium hydroxide 10.4 10.6 Fixer formulation (Composition A) Ammonium thiosulfate (72.5% W / V aqueous solution) 240 ml Sodium sulfite 17 g Sodium acetate trihydrate 6.5 g Boric acid 6.0 g Citric acid Sodium dihydrate 2.0g (Composition B) Pure water (ion exchange water) 17ml Sulfuric acid (50% W / V Aqueous) 4.7 g Aluminum sulfate 26.5g (AI ₂ O ₃ in terms of content of 8.1% W / aqueous V) fixer above composition A in water 500ml when using, dissolved in the order of composition B, was used finish 1l. The pH of the fixing solution was adjusted to 4.8 with acetic acid.

(Development Processing Conditions) (Process) (Temperature) (Time) Development 40 ° C. for 15 seconds Fixing 35 ° C. for 15 seconds Rinse at 30 ° C. for 10 seconds Drying at 50 ° C. for 10 seconds PD
Measured with A-65, the sensitivity of sample No.1 at a concentration of 3.0 was 100
The gamma was indicated by the tangent between the densities 0.3 and 3.0. A gamma value of less than 6 cannot be used, and a gamma value of 6 or more and less than 10 still has insufficient high contrast performance. With a gamma value of 10 or more, the image becomes ultra-high contrast,
It will be practical enough. The surface resistivity was measured on the side of the developed sample on which the antistatic layer was provided, using a Kawaguchi Electric super insulation meter R-503.

Table 2 shows the results.

[0141]

[Table 2]

As is clear from Table 2, when processed with a developer having a pH of less than 11, samples Nos. 2 to 11 according to the present invention showed
It can be seen that the surface resistivity is lower and the desensitization and softening with the passage of time are less than those in comparison.

[0143]

According to the present invention, it is possible to provide a silver halide photographic light-sensitive material having good aging performance even when processed with a developing solution having a pH of less than 11.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-2-32330 (JP, A) JP-A-2-170154 (JP, A) JP-A-64-90439 (JP, A) JP-A-2- 125248 (JP, A) JP-A-64-55549 (JP, A) JP-A-62-280733 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G03C 1/06 501 G03C 1/85 G03C 5/29 501

Claims (1)

(57) [Claims] An at least one photosensitive silver halide emulsion layer and at least one antistatic layer are coated on a support, and said photosensitive silver halide emulsion layer and / or an adjacent layer thereof are provided. An image forming method comprising: treating a silver halide photographic light-sensitive material containing at least one hydrazine derivative represented by the following general formula [A] or [B] with a processing agent having a pH of less than 11.0. . Formula (A) _{A-NHNH- COCO -N (R 1} ) (R 2) Formula (B) A-NHNH-COCO-O- R 3 wherein, A is a sulfonamide group, Wakashi alkylamino group
Or an ant optionally substituted with an alkylideneamino group
At least one sulfur or oxygen atom
Sulfonamide group, alkylamino group or alkyl
A heterocyclic group which may be substituted with a
And, R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, saturated or unsaturated, hydroxy group or an alkoxy group der
And at least one of R ₁ and R ₂ is an alkenyl group, an alkynyl group, a saturated heterocyclic group, a hydroxy group or an alkoxy group . R ₃ represents an alkynyl group or a saturated heterocyclic group. The compound represented by the general formula [A] or [B] includes a compound in which at least one H of -NHNH- in the formula is substituted with a substituent. ]