JPS63287860A - Photoconductive toner - Google Patents

Abstract

PURPOSE:To obtain the title toner having good photosensitivity, excellent dispersibility and thermal stability by incorporating a specified hydrazone compd. in the title toner as an electric charge transfer substance. CONSTITUTION:The title toner contains an electric charge generating substance 1 and the electric charge transfer substance 2 in particles composed of a thermoplastic resin 3 as a main component. The hydrazone compds. shown by formula I and/or formula II are incorporated in the title toner as the electric charge transfer substance 2. In formulas I and II, R1 is alkyl or aralkyl group, R2 and R3 are each alkyl or aryl group, etc., Z<1> and Z<2> are each hydrogen atom or alkyl group, etc., R4 and R5 are each hydrogen atom or aryl group, etc., (m) and (l) are each 1 or 2, (n) is 0 or 1. Thus, thermal stability and dispersibility of the title toner are improved, and the title toner having excellent photosensitivity and fixing property is obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention This invention relates to toners, particularly photoconductive toners, for use in electrophotography.

2. Description of the Related Art Image forming methods based on electrophotography are widely known. The usual method is to charge the entire surface of the photoreceptor by corona discharge, and then to form an electrostatic latent image by irradiating the photoreceptor with imagewise light. At this time, the exposed portion of the photoreceptor becomes conductive and the charge disappears, and the unexposed portion remains as an electrostatic latent image.

When toner of opposite polarity is brought close to this electrostatic latent image, the toner is electrostatically attracted and the latent image is visualized.

In one type of xerography, this is usually transferred and fixed, and in the electrofax method, it is directly fixed on a photoreceptor. The problem with these methods is that these steps are complicated, and the electrophotographic copying apparatus is complicated and expensive. In addition, since the copying system is constructed from one independent member, the photoreceptor and the toner powder, that is, the developer, if the performance of one of the two members deteriorates, e.g. , it becomes difficult to obtain high-quality copies due to optical fatigue of the photoreceptor or deterioration of the charging characteristics of the developer.
Therefore, in order to always maintain the desired performance of the photoreceptor and developer, there have been problems such as maintenance including the system becoming difficult.

In recent years, in order to solve these problems, a copying process has been proposed that does not use a photoreceptor but uses a photoconductive toner in which a developer is imparted with photoconductivity.

This method is a method in which the toner itself has the function of forming an electrostatic latent image, and since it does not require a photoreceptor, it has the advantage of simplifying electrophotographic copying equipment and lowering manufacturing costs.It also has the advantage of being able to produce full-color images in one shot. Research and development is being actively conducted on methods that can form images (for example, Japanese Patent Publication No. 56-28259, Japanese Patent Application Laid-Open No. 61-230154).
to 61-230158, etc.).

Examples of electrophotography using photoconductive toner include the Sugarman method (L]5P2758939), its modified methods include a combination method of photoconductive toner and corona discharge, and an electrophoresis method.

In order to realize the electrophotographic process described above, the development of photoconductive toner is the key, but such toner must have both functions as a developer and photoconductivity. Due to the difficulty, the photosensitivity in particular is far from a practical level, and it has not yet been put to practical use.

In Japanese Patent Publication No. 56-28259, it has been put to practical use as a photoconductive toner for marking. This toner uses zinc oxide as a photoconductive material with rose bengal as a sensitizer. However, the particle size of the toner is approximately 100 μm.
To a large extent, when considered as a toner for copiers, there is a problem in image quality, and a spray solution containing a solvent is used, making it unsuitable for copiers.

JP-A-61-230154 to JP-A-61-230158 disclose photoconductive toners, but the photoconductive substances are completely different.

Problems to be Solved by the Invention Photoconductive toners have particularly poor photosensitivity and lack practicality, so improvements are desired.

In view of these circumstances, it is an object of the present invention to provide a photoconductive toner with excellent photosensitivity and excellent fixing properties.

Furthermore, the present invention provides a photoconductive toner containing a photoconductive material that is thermally stable, has good dispersibility, and in which the toner powder layer sufficiently retains the required functionality. be.

Means for solving the problem, that is, the present invention provides a photoconductive toner containing a charge generating substance and a charge transporting substance in particles mainly composed of a thermoplastic resin. ] and/or (II).

(Left below) (In the formula, R+ IH represents an alkyl group, substituted alkyl group, or aralkyl group, and R2, Ra1d represents an alkyl group, substituted alkyl group, aryl group, phenyl group, naphthyl group, or aralkyl group.) ;(In the formula, zl, z2
represents a hydrogen atom, an alkyl group, an alkoxy group, a phenoxy group, or an arylalkoxy group, R4 and R5 represent a hydrogen atom, an alkyl group, 1 or 2, and n is 0
Or represents 1. ) The above general formulas [I] and (II)
Examples of the hydrazone compound represented by the above include those disclosed as materials for photoreceptors in JP-A-59-229564. However, no application is made to photoconductive toners.

The present invention relates to the general formula (Il) and/or the general formula [I
By using the hydrazone compound represented by [ ] as a charge transport substance in a photoconductive toner or in a charge transport layer of a functionally separated photoconductive toner, it is thermally stable and has good dispersibility; Furthermore, it is possible to produce a photoconductive toner that has excellent electrophotographic properties such as charge retention ability, photosensitivity, and reduced residual potential, and that exhibits stable properties even when used repeatedly.

The compound represented by the above general formula [■] can be easily synthesized by a conventional method.

That is, it can be produced by a conventional method from an aldehyde represented by the general formula and hydrazine represented by the general formula or a mineral acid salt thereof. That is, if necessary, a small amount of acid (glacial acetic acid or inorganic acid) is added as a reaction accelerator, and the above hydrazine is heated at 10 to 200°C in a non-reactive inert solvent such as alcohol, toluene, DMF, DMSO, etc.
It is obtained by carrying out a condensation reaction under the temperature conditions of

Further, the compound represented by the general formula (III) can also be obtained by a conventional method in the same manner as the compound CI) from an acrolein compound represented by the general formula and hydrazine or its mineral acid salt represented by the general formula.

Specific examples of 1 in general formula (I) include alkyl groups such as methyl, ethyl, propyl, ethyl, and hexyl; substituted alkyl groups such as 2-hydroxyethyl and 2-chloroethyl; benzyl groups; and aralkyl groups such as phenethyl group.

In consideration of photosensitivity, alkyl groups such as methyl, ethyl, propyl, and ethyl groups are particularly preferred.

Specific examples of R2 and R3 include methyl group, ethyl group,
Examples include alkyl groups such as propyl group, phenyl group, benzyl group, hexyl group, heptyl group, and octyl group; aryl group; phenyl group; naphthyl group; aralkyl group such as benzyl group and phenethyl group.

In consideration of photosensitivity, methyl, ethyl, phenyl, aryl, and naphthyl groups are particularly preferred.

General formula [1, zl and z2 are hydrogen atoms; alkyl groups such as methyl, ethyl, propyl, butyl, hexyl; alkoxy groups such as methoxy, ethoxy, butoxy; phenoxy; benzyloxy R4 and R5 represent a hydrogen atom; a lower alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group; an aryl group;
Phenyl group: represents an aralkyl group such as benzyl group or phenethyl group.

m and! represents 1 or 2, and n represents 0 or 1.

In the general formula (10), it is preferable that Zl and Z2 are an alkyl group or an alkoxy group, and R4 and R5 are a phenyl group or an aryl group.

Examples of the structure of the photoconductive toner of the present invention are shown schematically in FIGS. 1 and 2.

Figure 1 shows that the charge generating substance (1) is a hydrazone compound (2).
) and a dispersed photoconductive toner (hereinafter referred to as "dispersed photoconductive toner") which is dispersed in a thermoplastic resin (3).

Figure 2 shows a coated photoconductive material in which a thermoplastic resin (3) in which a charge-generating substance (1) is dispersed is coated around a nuclear core substance (4) containing a hydrazone compound (2). A toner (hereinafter referred to as a "coated photoconductive toner"). A coated photoconductive toner can improve light transmittance, and even when a single toner layer is formed into multiple layers, it is very advantageous in terms of photosensitivity.

Dispersed photoconductive toner can be produced by applying a known method. For example, it can be produced by dispersing a charge generating substance in a solution containing a hydrazone compound and a thermoplastic resin solution, and then using a spray drying method. Alternatively, it may be produced by a thermal crosstalk method without using a solvent, and is not particularly limited.
m, more preferably a particle size of 8 to 20 μm (this is adjusted).

If it is smaller than 1 .mu.m, the fluidity, development characteristics, etc. when formed into a toner will be poor, and the photosensitivity will also be significantly lowered. 3
If it is larger than 0 μm, the final image, especially the resolution, will be poor. At this time, the hydrazone compound is 5 to 90W [%,
It is preferably contained in an amount of 10 to 5 Qwt%.

If it is less than 5 wL%, the carrier transport ability will be poor, resulting in insufficient photosensitivity and high residual potential. 90W [%
If the amount is larger than that, the binding property with the resin will be poor, and the hydrazone compound will precipitate, making granulation difficult.

Examples of the charge generating substance include amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide, cadmium selenide, mercury sulfide, lead oxide,
Inorganic substances such as lead sulfide and amorphous silicon, azo dyes such as monoazo, disazo, and trisazo dyes, perylene dyes, anthraquinone dyes, polycyclic quinone dyes,
Indigoid dyes, phthalocyanine dyes, carbonium dyes, quinoneimine dyes, methine dyes, quinoline dyes, nitroso dyes, nitrone dyes, benzoquinone and naphthoquinone dyes, phthalimide dyes, perinone dyes or quinacridone dyes Examples include organic substances such as dyes.

These may be used alone or in combination of two or more.

Among the above substances, disazo compounds represented by the following general formula [■] are particularly preferred.

(In the formula, A represents a phenyl group which may have a phenylene substituent which may have a substituent) General formula (III)
The compound represented by can be easily synthesized by a conventional method.

That is, the dinitro compound represented by the general formula is reduced with a reducing agent such as zinc-calcium chloride or tin chloride-hydrochloric acid to obtain the diamino compound represented by the general formula (IX).

The N-N diamino compound is tetrazotized using sodium nitrite-hydrochloric acid and coupled with a suitable coupler component Y represented by 1 to 9 below in the presence of an alkali, or the diamino compound is tetrazotized and then HB F4
It can be synthesized by adding an acid such as, isolating it in the form of a salt, and then performing a coupling reaction.

Specific examples of the coupler component Y include, but are not limited to, the following.

The charge generating substance has a power of 1 to 90 W[%, preferably 5 to 50
W[%]. If the amount is less than 1 wt%, photosensitivity and coloring power will be insufficient. If the amount is more than 9QWtX, the binding property with the resin will be poor and granulation will be difficult. Furthermore, when the toner is multilayered, there are problems in that light does not reach the layers below, the photosensitivity deteriorates, and the residual potential increases. Note that a conductive substance may be added as necessary to suppress the increase in residual potential. If the amount of conductive material is large, problems such as increased dark decay and poor charging properties will occur =
18- 20W [% or less is desirable.

Thermoplastic resins include polyethylene resin, acrylic resin, methacrylic resin, polyester resin, polyamide resin, polyethylene, polypropylene, polyvinylidene fluoride, polyvinylidene chloride, polyvinyl chloride,
Ethylene-vinyl acetate copolymer, styrene-acrylic ester copolymer, styrene-methacrylic ester copolymer, styrene-butadiene copolymer, styrene-vinylidene chloride copolymer, styrene-vinyl chloride copolymer, styrene -vinylidene fluoride copolymer, styrene-acrylonitrile copolymer, epoxy resin, modified rosin,
Polyethylene wax, polycarbonate resin, etc. can be used alone or in combination.

In addition, when the photoconductive toner of the present invention is used particularly as a toner for pressure fixing, the thermoplastic resin may include polyolefins (low molecular weight polyethylene, low molecular weight polypropylene, oxidized polyethylene, poly(47-sodified ethylene), etc.),
Epoxy resin, polyester resin (acid value 10 or less), styrene-butadiene copolymer (monomer ratio 5-30:
95-70), olefin copolymers (ethylene-acrylic acid copolymers, ethylene-acrylic ester copolymers, ethylene-methacrylic acid copolymers, ethylene-methacrylic ester copolymers, ethylene-vinyl chloride copolymers) Polyvinyl pyrrolidone, methyl vinyl ether-maleic anhydride copolymer, maleic acid-modified phenol resin, phenol-modified terpene resin, etc. can also be used.

In the case of a coated photoconductive toner, it can be obtained by further forming a layer containing a charge generating substance on the core material. As the binder resin, the same thermoplastic resin as described above can be used. For example, a layer containing a charge generating substance can be coated on the core material by a spray drying method, or a thermoplastic resin monomer can be used. A method for producing a multilayered polymer by a method such as emulsion polymerization or suspension polymerization can be used.

The thickness of the coating layer is in the range of 0.1 to 10 μm, preferably 0.1 to 2 μm, and depending on the type and amount of each composition, the actual chargeability, photoconductivity, and Appropriate conditions are selected depending on the characteristics such as print density when forming an image.

The amount of the charge generating substance contained in the coating layer is 5 to 100%VL%, preferably 20 to 80W%, more preferably 30 to 60W%, based on the total amount of the coating layer.
%. If it is less than 5WL%, the photosensitivity will generally be poor, and the print density as a final image may also be insufficient.

The particle size of the core material is closely related to the particle size of the final photoconductive toner, and is related to the final image quality and resolution, and is usually 1 to 30 μm, preferably 5 to 20 μm.
It belongs to m. If it is smaller than 1 μm, the fluidity, development characteristics, and photosensitivity of the toner will be poor;
If it is thicker than μm, the final image quality, especially resolution and development characteristics, will be poor.

Note that, although it is desirable that the nuclear core material is spherical, the shape is not limited.

As the thermoplastic resin used for the nuclear core substance, the same thermoplastic resins as those described above can be used, and thermoplastic resins, or in addition to thermoplastic resins, the hydrazone compound according to the present invention, etc. It is also possible to use granules obtained by granulating the various components obtained by heat kneading and pulverizing. Alternatively, by emulsion polymerization or suspension polymerization of a mixture of thermoplastic binder resin monomer or prepolymer, hydrazone compound, and various other components, or by spray drying after dissolving the resin and hydrazone compound in a solvent. It may also be obtained by a granulation method or the like.

The amount of the hydrazone compound to be added is preferably one that does not precipitate when the core particles are prepared together with the thermoplastic resin, and it varies depending on the type of resin and hydrazone compound, or whether one or more types are added. Approximately 0.1 to 95 W [%, preferably 30 to B] based on the amount of resin
□wt%, more preferably 40 to 13Q wt%. If it is less than Q, l WL%, the carrier transport ability in the core material will be poor, and if it is more than 95W%, the hydrazone compound will usually precipitate in the resin, making granulation difficult.

Of course, a single hydrazone compound or a plurality of hydrazone compounds may be used as the charge transporting substance, or a charge transporting substance other than the hydrazone compound may be used in combination.

The coating layer containing the charge-generating substance may also contain a hydrazone compound to increase photosensitivity (
Figure 3). In this case as well, the hydrazone compound may be the same as the hydrazone compound containing one core substance, or a different hydrazone compound may be used. Of course, they may be added singly or in combination, or may be used in combination with charge transport substances other than hydrazone compounds.

When a hydrazone compound is allowed to coexist in the coating layer, the amount of the hydrazone compound to be contained is 0 to 80 wL%, preferably 0.1 to 50 wL% based on the total amount of the coating layer.
WL%, more preferably 1 to 3 ow [%]. 80
If the amount is more than W%, a hydrazone compound may precipitate, making it difficult to form a coating layer.

By including a hydrazone compound in the coating layer, not only does the movement of photogenerated carriers in the coating layer become easy, but also the movement of carriers between the nuclear core material and the coating layer becomes easy, which improves photosensitivity. improvement is achieved.

A toner showing another aspect of the present invention includes a nuclear core material (
4), a hydrazone compound (2) and a charge generating substance (1)
), a photoconductive toner (Figure 4) containing a charge generating substance (1) in the coating layer, a nuclear core substance (4) and a charge generating substance (1) and a hydrazone compound (2) in both layers of the coating layer. ) A photoconductive toner containing both substances (Fig. 5), a photoconductive toner containing a charge generating substance (1) in the nuclear core material (4), and a hydrazone compound (2) in the coating layer (Fig. 6), a nuclear core material (Fig. The substance (4) is a charge generating substance (1), and the coating layer is a charge generating substance (1) and a hydrazone compound (
2) (Fig. 7), a toner (Fig. 8) containing a hydrazone compound (2) and a charge generating substance (1) in the core substance (→) and a charge generating substance (1) in the coating layer,
Alternatively, the nuclear body core 1 substance (4) does not contain anything, and the coating layer contains a charge generating substance (1) and a hydrazone compound (
2) (FIG. 9) and the like.

In order to take advantage of the coating type photoconductive toner, which can obtain sufficient light transmittance and good photosensitivity, it is necessary to use a coating layer containing a core substance containing a hydrazone compound and a charge generating substance. Photoconductive toners formed therein, ie, photoconductive toners of the embodiments shown in FIGS. 2-5, are preferred.

Colorants include known pigments or dyes, such as carbon black, nigrosine dye, aniline blue, calco oil blue, chrome yellow, ultramarine blue, typhon oilet, quinoline yellow, methylene blue chloride, phthalocyanine blue, and malachite green. Oxalate, lamp blank, oil black, azo oil blank, rose bengal, etc.
It may be anything or a mixture thereof.

In addition, as a sensitizer, chloranil, tetracyaphenalene, 2,4,7-) dinitro-9-alolenon, 5
．． Electron-withdrawing sensitizers such as 6-dicyazbenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid, methyl hyolet, rhodamine B, cyanine dye, pyrylium salt, thiapyrylium It is also possible to use salt and the like.

In the photoconductive toner of the present invention, known additives may be used as appropriate within the range that does not impede the objects and effects of the present invention. As such additives, wax etc. can be added to improve fixing properties, and conductive substances such as fine metal oxide powder can be added to further improve photoconductivity.
In particular, it is possible to reduce the residual potential. Furthermore, in order to improve the properties as a toner, magnetic powder, colorant, charge control agent, fluidizing agent, etc. can be added as appropriate.

In particular, in the case of a coated photoconductive toner, a conductive substance such as wax or fine metal oxide powder can be added to the core substance to improve fixing properties and conductivity.

The coating layer 1 may contain a charge control agent, a fluidizing agent, a wax, etc. to improve charging properties, fluidity, and fixing properties.

In addition, when used as a toner containing a magnetic material, cobalt, a magnetic material that is chemically stable and can be easily formed into fine particles with a particle diameter of 1 μ or less is used. Metals like iron, nickel, nialium, cobalt, copper, iron, lead, magnesium, nickel, tin, zinc, antimony, beryllium, bismuth,
cadmium, calcium, manganese, selenium, titanium,
Alloys of metals and mixtures thereof such as tungsten, vanadium; metal compounds including metal oxides such as aluminum oxide, iron oxide, copper oxide, nickel oxide, zinc oxide, titanium oxide, and magnesium oxide; vanadium nitride, chromium nitride Refractory materials such as tungsten carbide, carbides such as tungsten carbide, ferrites and mixtures thereof, etc. may be used.

It is desirable that these ferromagnetic materials have an average particle size of about 0.1 to 1 μm, and the amount to be included in the toner is approximately 50 to 300 parts by weight per 100 parts by weight of the resin component.
Particularly preferably 90 to 2 parts by weight per 100 parts by weight of the resin component.
00 parts by weight.

When the purpose is a color magnetic toner, -Fe20
□ type brown magnetic material or magnetic powder whose color is hidden by surface treatment is used.

Further, the toner of the present invention can be used together with a fluidizing agent if necessary, and the fluidizing agent is preferably a fine powder of hydrophobic silica, titanium oxide, aluminum oxide, etc., and the amount used is determined according to the toner. 0.1 to 1 w
t% is preferred.

The photoconductive toner of the present invention can be used in a copying machine that does not have a photoreceptor. Therefore, the simplification of copying machines,
A reduction in manufacturing costs can be achieved. The photoconductive toner of the present invention can also be used in conventional copying machines.

The present invention will be explained below with reference to Examples, but the present invention is not limited to these examples.

Example 1 Styrene acrylic copolymer resin (SBM73, manufactured by Sanyo Chemical Industries, Ltd.) 100 parts by weight Diazo component Disazo compound obtained from coupler component Y (↓)
30 parts by weight N-ethylcarbazole-3-aldehydemethylphenylhydrazone (formula (IA) below) C,H.

Viscole 550P (manufactured by Eyo Kasei Kogyo Co., Ltd.) 5
Part by weight After thoroughly mixing the above materials in a ball mill, 140
The mixture was kneaded on a triple roll heated to ℃.

After cooling, the mixed material was roughly pulverized in a feather mill, then pulverized in a pulverizer using a jet stream, and further classified by air to obtain a photoconductive toner (■) having an average particle size of 13 μm.

Example 2 Styrene acrylic copolymer resin (SBM73 manufactured by Sanyo Chemical Co., Ltd.) 100 parts by weight Diazo component Disazo compound obtained from coupler component Y (4)
30 parts by weight N-ethylcarbazole-3-aldehyde diphenylhydrazone (formula (I-B) below) Viscole 550 P (manufactured by Sanyo Chemical Industries, Ltd.) 5
The average particle size of the weight part was 12 μm using the same method as in Example 1.
A photoconductive toner (■) was obtained.

Example 3 Styrene 70 parts by weight! -! l-
Azobisisoputiloni) IJ (polymerization initiator) 2 parts by weight A hydrazone compound represented by the following structural formula (IC) A hydrazone compound represented by the following structural formula (It-A) Dispersed in a uniform dispersion of the above composition As a medium, 400 parts by weight of a 0.8 WL% methyl cellulose aqueous solution and 0.1 parts by weight of sodium lauryl sulfate were added, and homomixing was performed at 5000 rPm for 10 minutes at room temperature. This mixture was degassed and replaced with nitrogen, then heated to 70°C, and polymerized for 6 hours while stirring normally. Add this solution to 2 parts distilled water! After repeating the operation of placing the particles in a container and performing decantation three times, the particles were separated using a centrifugal separator and dried to obtain microparticles with an average particle size of 10 μm.

Thermoplastic resin styrene 70 parts by weight n-butyl methacrylate 20 parts by weight Diethylaminomethacrylate 10 parts by weight Copolymer (softening point 132
℃, glass transition point 58℃) 10 parts by weight Disazo compound obtained from coupler component Y (1)
30 parts by weight of the above compound (I-C
) 10 parts by weight 0.3 parts by weight or more of pyromellitic anhydride represented by the following structural formula are uniformly dispersed and stirred in toluene by high shear stirring, and then the nuclei produced in (a) are prepared. As a result of adding a core material and spray-drying the surface coating by a streaky seed dry method, a photoconductive toner (■) having an average particle size of 11 μm and a surface coating layer of 1.0 μm was obtained.

The photoconductive toners 1 to 3 obtained in Evaluation Examples 1 to 3 were uniformly spread on a brass substrate to form a thin toner layer.
-5xv corona charging was applied to uniformly charge the toner layer, and then imagewise exposure was performed to form an electrostatic latent image on the toner layer. Next, plain paper was brought into close contact with the paper, and corona charging was performed at 15 KV, which had a polarity opposite to that of the charging electrode based on the paper value, to transfer the toner in the latent image onto the plain paper, and then heat fixation was performed. A clear reddish-purple to reddish-brown image was obtained.

Effects of the Invention According to the present invention, a photoconductive toner having good photosensitivity, excellent dispersibility, and thermal stability can be obtained.

[Brief explanation of the drawing]

1 to 9 are schematic cross-sectional views showing one embodiment of the photoconductive toner of the present invention. (1)...Charge generating substance (2)...Hydrazone compound (3)...Thermoplastic resin (4)...Nuclear body core material

Claims (1)

[Claims] 1. In a photoconductive toner containing a charge generating substance and a charge transporting substance in particles mainly composed of a thermoplastic resin, the charge transporting substance is represented by the following general formula [I] and/or [II]. ] A photoconductive toner characterized by containing a hydrazone compound represented by; R_2 and R_3 represent an alkyl group, a substituted alkyl group, an aryl group, a phenyl group, a naphthyl group, or an aralkyl group.); ▲There are numerical formulas, chemical formulas, tables, etc.▼[II] (In the formula, Z^1, Z^2 represents a hydrogen atom, an alkyl group, an alkoxy group, a phenoxy group, or an arylalkoxy group, and R_4 and R_5 represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a phenyl group, a naphthyl group, or an aralkyl group; and l represents 1 or 2, and n represents 0 or 1.) 2. Claim 1, characterized in that the charge generating substance contains a disazo compound represented by the following general formula [III]. Photoconductive toner described in section; ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [III] (In the formula, A represents a phenylene group or naphthylene group that may have a substituent, and X is a ▲ mathematical formula, chemical formula, table, etc.) ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ where R represents a hydrogen atom, an alkyl group, or a phenyl group that may have a substituent. .)