JPH06266128A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To provide an electrophotographic sensitive body having excellent electrophotographic performance, that is, high sensitivity, low residual potential and satisfactory image characteristics by forming a photosensitive layer on an electric conductive substrate and incorporating a specified compd. as an electric charge transferring material into the photosensitive layer. CONSTITUTION:When a photosensitive layer is formed on an electric conductive substrate to obtain an electrophotographic sensitive body, a compd. represented by the formula is incorporated into the photosensitive layer. In the formula, (l) is an integer of >=0, (m) is an integer of >=0, (n) is an integer of >=1, m>=2 in the case of l=0, m>=1 in the case of l>=1, m>=0 in the case of l>=2, RA is nitro, OH, halogen, CF3, alkyl, alkoxy, aryl, aralkyl, alkyl, amino, CONH2, COORA', C0NHRA', CON(RA')2 or CORA', each of the alkyl, alkoxy, aryl, aralkyl, alkyl and amino may have a substituent, RA' is alkyl, aryl or aralkyl, each of the alkyl, aryl and aralkyl may have a substituent, and in the case of n>=2, plural RA's may be different from each other.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an electrophotographic photosensitive member for forming an electrostatic latent image. More specifically, it relates to an electrophotographic photoreceptor having a layer containing a compound having an electron transporting ability.

[0002]

2. Description of the Related Art Conventionally, electrophotographic photoreceptors using organic photoconductors have been variously studied because of their advantages such as pollution-free, high productivity and low cost. It is put to practical use as a photoreceptor. These electrophotographic photoreceptors include a laminated type and a single layer type, but a photoreceptor using an organic photoconductor generally has a charge generation layer that generates a charge by light irradiation and a charge that transports the generated charge. It has a laminated structure consisting of a transport layer. In this case, as the charge transport material used in the charge transport layer, a polymer material such as poly-N-vinylcarbazole or a low molecular weight compound such as pyrazoline, hydrazone or triphenylamine derivative is used.

However, since all of these charge-transporting substances have a hole-transporting ability, most of the developing systems adopting a negative charge on the surface of the photoconductor are adopted.
For this reason, the toner that has been conventionally used in high-speed machines cannot be used, and there are few high-quality toners at present. Further, when the surface of the photoconductor is negatively charged as described above, there is a problem that not only the ozone is generated due to the reaction with oxygen in the air at the time of charging to harm the environment but also the surface of the photoconductor is deteriorated.

On the other hand, a positive charging laminated photoreceptor having a charge transport layer on the lower side and a charge generation layer on the upper side has been developed by reversing the layer structure of the photosensitive layer of the laminated photoreceptor. Since the charging potential is low and the printing durability is poor, a protective layer is further provided on the charge generation layer.

[0005]

In order to solve the above problems, a photoconductor in which a charge transport material having an electron transporting property is used in a charge transport layer and the surface of the photoconductor is positively charged. Should be configured. 2,4,7-Trinitro-9-fluorenone is known as such an electron-transporting material, but its solubility is poor and it is not possible to obtain practical sensitivity by combining it with an existing charge-generating substance. It was In addition, 2, 4,
As a result of improved studies on 7-trinitro-9-fluorenone, in recent years, an electron transporting substance having a solubilizing group introduced into an electron acceptor structure has been proposed. For example, Japanese Patent Laid-Open No. 1-206349
No. 2-135362, No. 2-214866, No. 3-290666 and “Japan Hardcopy '92” Proceedings, 173, (1992). However, in the present situation, when any of the compounds is combined with an existing charge generating substance to form a photoreceptor, the sensitivity is still insufficient in practical use, and a good image cannot be obtained.

[0006]

SUMMARY OF THE INVENTION The present invention has been made in view of the above problems.
An object of the present invention is to provide an electrophotographic photosensitive member using a charge transporting material having an electron transporting ability.

Another object of the present invention is to provide a laminate type electrophotographic photoreceptor for positive charging, which has excellent electrophotographic performance, that is, high sensitivity, low residual potential and good image characteristics.

[0008]

As a result of research, the present inventors have found that the object of the present invention can be achieved by any of the following electrophotographic photoreceptors. That is, in an electrophotographic photosensitive member in which a photosensitive layer is provided on a conductive support, the constitutional parameters are specified as a charge transport substance in the photosensitive layer, and "Chemical formula 1",
General formulas [A], [B], [C] described in "Chemical formula 3", "Chemical formula 5", "Chemical formula 7", "Chemical formula 9", "Chemical formula 11" and "Chemical formula 13",
The object of the present invention can be achieved by incorporating any one of the compounds represented by [D], [E], [F] and [G].

In a preferred embodiment of the present invention, there are provided general formulas [a] to [g] corresponding to the general formulas [A] to [G] with further structural restrictions. Included are the compounds shown.

The high performance of the present invention as a charge transport material is
It seems that the long-term compatibility with the binder is kept stable as compared with the conventional charge transport material.

Next, specific examples of the compounds represented by the above general formula and synthetic examples thereof will be shown.

(A) Compound represented by the general formula [A]: Exemplified compound:

[0013]

[Chemical 15]

[0014]

[Chemical 16]

[0015]

[Chemical 17]

[0016]

[Chemical 18]

[0017]

[Chemical 19]

: Synthesis example:

[0019]

[Chemical 20]

Exemplified Compound A-16 was synthesized according to the above synthetic route. Using 2,5-bis (trifluoromethyl) aniline (manufactured by Aldrich) as a starting material, a known method (J.Ch
Compound 4 was synthesized according to em, Soc, 1071-6 (1954)).

10 g of compound 4 was placed in a 100 ml four-headed flask, and 20 g of zinc chloride, 5 g of 2,6-xylidine 5 (manufactured by Wako Pure Chemical Industries, Ltd.) and 100 ml of o-dichlorobenzene (hereinafter abbreviated as ODB) were added. Then, the mixture was heated to reflux for 50 hours with an ester tube and a thermometer attached. After allowing to cool, the solid is removed by suction filtration and washed well with ethyl acetate. The solvent of the mother liquor was distilled off under reduced pressure, and the residue was applied to a silica gel column. The toluene: n-hexane = 1: 1 eluate was crystallized from n-hexane to obtain 9.5 g (yield 75%) of a red powder of Exemplified Compound A-16. Melting point was measured by the Japanese Pharmacopoeia Melting point measurement result 153-155 ° C
Met. Since the elemental analysis values also agreed well with the calculated values, the structure of Exemplified Compound A-16 was confirmed.

C H N calculated value 59.15% 2.90% 2.87% measured value 58.51% 3.01% 2.73% (B) compound represented by general formula [B]: exemplified compound:

[0023]

[Chemical 21]

[0024]

[Chemical formula 22]

[0025]

[Chemical formula 23]

[0026]

[Chemical formula 24]

[0027]

[Chemical 25]

[0028]: Synthesis example:

[0029]

[Chemical formula 26]

Exemplified Compound B-2 was synthesized according to the above synthetic route. Using 2-iodobenzotrifluoride (manufactured by Aldrich) as a starting material, a known method (J. Chem, So
c, 1071-6 (1954)), compound 4 was synthesized.

10 g of compound 4 was placed in a 100 ml four-headed flask, 20 g of zinc chloride, 5 g of 2,6-xylidine 5 (manufactured by Wako Pure Chemical Industries, Ltd.) and 100 ml of ODB were added, and an ester tube and a thermometer were attached, The mixture was heated under reflux for 50 hours. After cooling, the solid is removed by suction filtration and washed well with ethyl acetate and chloroform. The solvent of the mother liquor was distilled off under reduced pressure, and the residue was applied to a silica gel column. The eluate of toluene: n-hexane = 1: 1 was crystallized with n-hexane to obtain 8.5 g (yield 64%) of a red powder of Exemplified Compound B-2. The melting point was 189 to 190 ° C as measured by the Japanese Pharmacopoeia melting point measuring method. Since the elemental analysis values were in good agreement with the calculated values, Exemplified Compound B
-2 structure was confirmed.

C H N calculated value 59.87% 3.20% 9.52% measured value 59.71% 3.31% 9.40% (C) Compound represented by general formula [C]: Exemplified compound:

[0033]

[Chemical 27]

[0034]

[Chemical 28]

[0035]

[Chemical 29]

[0036]

[Chemical 30]

[0037]

[Chemical 31]

[0038]

[Chemical 32]

: Synthesis example:

[0040]

[Chemical 33]

Exemplified compound C-1 was synthesized according to the above synthetic route. Using 9-fluorenone-4-carboxylic acid (manufactured by Aldrich) as a starting material, according to a conventional method,
Compound 3 was synthesized.

10 g of compound 3 was placed in a 100 ml four-headed flask, 20 g of zinc chloride, 5 g of 2,6-xylidine 5 (manufactured by Wako Pure Chemical Industries, Ltd.) and 100 ml of ODB were added, and an ester tube and a thermometer were attached. The mixture was heated under reflux for 50 hours. After allowing to cool, the solid is removed by suction filtration and washed well with ethyl acetate. The solvent of the mother liquor was distilled off under reduced pressure, and the residue was applied to a silica gel column. Toluene: n-hexane = 1: 1 eluate was crystallized from n-hexane to give 6.8 g of Exemplified Compound C-1 red powder (yield 56
%) Was obtained. The melting point was 193-196 ° C as measured by the Japanese Pharmacopoeia melting point measuring method. Since the elemental analysis values also agreed well with the calculated values, the structure of the exemplified compound C-1 was confirmed.

C H N calculated value 68.04% 5.90% 7.93% Actual value 67.59% 6.05% 7.72% (D) Compound represented by general formula [D]: Exemplified compound:

[0044]

[Chemical 34]

[0045]

[Chemical 35]

[0046]

[Chemical 36]

[0047]

[Chemical 37]

[0048]

[Chemical 38]

: Synthesis example:

[0050]

[Chemical Formula 39]

Exemplified Compound D-2 was synthesized according to the above synthetic route. Compound 1 as a starting material, the known methods (J.
Compound 4 was synthesized according to Chem, Soc, 1071-6 (1954)).

10 g of compound 4 was placed in a 100 ml four-headed flask, 20 g of zinc chloride, 5 g of 2-ethylaniline 5 (manufactured by Aldrich) and 100 ml of ODB were added, and the mixture was heated under reflux for 120 hours with an ester tube and a thermometer attached. . After allowing to cool, the solid is removed by suction filtration and washed well with DMSO. The solvent of the mother liquor was distilled off under reduced pressure, and the residue was applied to a silica gel column. The toluene: n-hexane = 9: 1 eluate was crystallized from toluene to give 9.9 g of a dark red powder of Exemplified Compound D-2 (yield 78
%) Was obtained. The melting point was 193-194 ° C. as measured by the Japanese Pharmacopoeia melting point measuring method. Since the elemental analysis values were in good agreement with the calculated values, the structure of Exemplified Compound D-2 was confirmed.

C H N calculated value 56.80% 3.97% 2.76% Actual value 56.62% 4.01% 2.51% (E) Compound represented by general formula [E]: Exemplified compound:

[0054]

[Chemical 40]

[0055]

[Chemical 41]

[0056]

[Chemical 42]

[0057]

[Chemical 43]

[0058]

[Chemical 44]

: Synthesis example:

[0060]

[Chemical formula 45]

Exemplified compound E-1 was synthesized according to the above synthetic route. Using 2,7-dinitrofluorenone (manufactured by Aldrich) as a starting material, a known method (Japanese Patent Laid-Open No. 1-290654)
Compound 2 ) was synthesized.

Compound 2 ; 10 g was placed in a 100 ml four-headed flask, 20 g of zinc chloride, 5 g of 2-ethylaniline 3 (manufactured by Aldrich) and 100 ml of ODB were added, and the mixture was heated under reflux for 60 hours with an ester tube and a thermometer attached. did. After allowing to cool, the solid is removed by suction filtration and washed well with ethyl acetate. The solvent of the mother liquor was distilled off under reduced pressure, and the residue was applied to a silica gel column. Toluene: n-hexane = 1: 1 eluate was crystallized from n-hexane to give 6.8 g of red powder of Exemplified Compound E-1 (yield 52
%) Was obtained. The melting point was 176 to 178 ° C as measured by the Japanese Pharmacopoeia melting point measuring method. Since the elemental analysis values also agreed well with the calculated values, the structure of Exemplified Compound E-1 was confirmed.

C H N calculated value 55.77% 3.12% 9.29% measured value 55.72% 3.14% 9.10% (F) Compound represented by general formula [F]: Exemplified compound:

[0064]

[Chemical formula 46]

[0065]

[Chemical 47]

[0066]

[Chemical 48]

[0067]

[Chemical 49]

[0068]

[Chemical 50]

[0069]

[Chemical 51]

[0070]

[Chemical 52]

: Synthesis example:

[0072]

[Chemical 53]

Exemplified compound F-1 was synthesized according to the above synthetic route. Known method using 3-methyl-4-aminobenzonitrile as a starting material (J. Chem, Soc, 1071-6 (1954))
According to the above, compound 4 was synthesized.

Compound 4 ; 10 g was placed in a 100 ml four-headed flask, 20 g of zinc chloride, 5 g of 2,6-xylidine 5 (manufactured by Wako Pure Chemical Industries, Ltd.) and 100 ml of ODB were added, and an ester tube and a thermometer were attached. The mixture was heated under reflux for 75 hours. After allowing to cool, the solid is removed by suction filtration and washed well with ethyl acetate. The solvent of the mother liquor was distilled off under reduced pressure, and the residue was applied to a silica gel column. The toluene: n-hexane = 1: 1 eluate was crystallized from n-hexane to give 11.9 g of brown crystals of the exemplified compound F-1 (yield
84%). The melting point was measured in accordance with the Japanese Pharmacopoeia melting point measurement method and was found to be 159 to 160 ° C. Since the elemental analysis values also agreed well with the calculated values, the structure of the exemplified compound F-1 was confirmed.

C H N calculated value 82.97% 4.93% 12.09% measured value 82.93% 4.95% 12.03% (G) compound represented by general formula [G]: exemplified compound:

[0076]

[Chemical 54]

[0077]

[Chemical 55]

[0078]

[Chemical 56]

[0079]

[Chemical 57]

[0080]

[Chemical 58]

: Synthesis example:

[0082]

[Chemical 59]

Exemplified compound G-1 was synthesized by the above reaction.

That is, 2,4,7-trinitrofluorenone1
(Tokyo Kasei Co., Ltd.) 10g in a 100ml four-headed flask, salt
20 g zinc oxide and 2-aminobiphenylTwo(Aldrich
10 g) and ODB 100 ml, and connect the ester tube and thermometer.
And heated to reflux for 80 hours. After cooling, the solid is removed by suction filtration.
And wash well with ethyl acetate. Distill off the solvent of mother liquor under reduced pressure
It was removed and the residue was applied to a silica gel column. toluene:
Crystallize the n-hexane = 1: 1 eluate with toluene
To give 12.1 g (yield 81%) of red crystals of Exemplified Compound G-1.
Obtained. The melting point is the result of measurement according to the Japanese Pharmacopoeia melting point measurement method.
It was 181-183 ° C. The elemental analysis values agree well with the calculated values.
This confirmed the structure of Exemplified Compound G-1.

C H N calculated value 64.38% 3.03% 12.01% measured value 64.21% 3.07% 11.92% In the electrophotographic photosensitive member of the present invention, examples of the conductive support include metal pipes, metal plates, metal sheets, and metal foils. ,
A conductive polymer film, a polymer film provided with a vapor deposition layer of a metal such as Al, a polymer film coated with a metal oxide, a quaternary ammonium salt, or the like, or paper is used.

In the electrophotographic photosensitive member of the present invention, the photosensitive layer is provided on the conductive support, but the photosensitive layer may have a single layer structure or a laminated structure in which the charge generation layer and the charge transport layer are functionally separated. It may be one. An adhesive layer may be provided between the conductive support and the photosensitive layer.

As shown in FIG. 1A, the photoconductor of the present invention comprises a charge generating layer (CGL) 2 containing a charge generating substance (CGM) as a main component and a charge transporting substance () on a conductive support 1. CT
A photosensitive layer 4 formed of a laminate with a charge transport layer (CTL) 3 containing M) as a main component is provided. As shown in FIG. 2B, the photosensitive layer 4 may be provided via the intermediate layer 5 provided on the conductive support 1. Thus, when the photosensitive layer 4 has a two-layer structure, a photoreceptor having the most excellent electrophotographic characteristics can be obtained. Further, in the present invention, FIG.
And a layer 6 containing the CTM as a main component as shown in (d).
A photosensitive layer 4 having fine particle-shaped CGM 7 dispersed therein may be provided directly on the conductive support 1 or via the intermediate layer 5.

Further, a protective layer (OCL) may be provided on the photosensitive layer 4 if necessary.

CGL constituting the photosensitive layer 4 having a two-layer structure
2. The CTL 3 may be formed by the following method depending on the characteristics of CTM and CGM, directly or on the conductive support 1 which is the lower layer surface, or when an intermediate layer such as an adhesive layer or a barrier layer is provided if necessary. it can.

(1) Vapor deposition method (2) Coating method a) Method of coating a solution coating prepared by dissolving CGM and CTM in a suitable solvent.

B) A method in which CGM and CTM are made into fine particles in a dispersion medium by a ball mill, a homomixer or the like, and a dispersion coating material obtained by mixing and dispersing with a binder as necessary is applied.

Examples of the vapor deposition method include a vacuum vapor deposition method, a sputtering method, an ion plating method, a CVD method and the like, and a paint coating method includes a dipping method, a spray method, an air doctor method, a doctor blade method and a reverse method. An appropriate method is selected according to the physical properties of the coating material such as the roll method.

The adhesive layer is formed of a resin alone, a coating of a dispersion of a low resistance compound such as tin oxide, indium oxide or titanium oxide in a resin, or aluminum oxide, zinc oxide or silicon oxide. The vapor deposition film of
The resin used for the adhesive layer is not particularly limited, and examples thereof include vinylidene chloride-vinyl chloride copolymer, water-soluble polyvinyl butyral resin, alcohol-soluble polyamide resin, vinyl acetate-based resin, polyvinyl alcohol, nitrocellulose, and polyimide resin. To be

The thickness of the binder layer is preferably about 0.01 to 10 μm, particularly preferably 0.01 to 1 μm.

When the photosensitive layer is a single layer, the compound represented by the above general formulas [A] to [G] is contained as a sensitizer in the photosensitive layer composed of a known material such as polyvinylcarbazole. And those containing the compounds represented by the above general formulas [A] to [G] as an electron transporting substance in a photosensitive layer containing a known charge generating substance.

On the other hand, when the photosensitive layer is a laminated type,
The charge generation layer may be obtained by vapor deposition of a charge generation substance on a conductive support, or may be formed by applying a coating liquid containing a charge generation substance and a binder resin as main components.

Any known charge generating substance and binder resin can be used.

For example, as the charge generating substance, an inorganic semiconductor such as Te-Se, an organic semiconductor such as polyvinylcarbazole, a bisazo compound, a trisazo compound, a metal-free phthalocyanine compound, a metal phthalocyanine compound,
Organic pigments such as pyrylium compounds, squarylium compounds, cyanine compounds, perylene compounds and polycyclic quinone compounds can be used. Among them, preferable charge generating substances include, for example, Y-type titanyl phthalocyanine pigments having an X-ray diffraction peak at 27.2 ° in JP-A-64-17066,
A having an X-ray diffraction peak at 26.3 ° in JP-A-62-67094
Type titanyl phthalocyanine pigment, B type titanyl phthalocyanine pigment having an X-ray diffraction peak at 28.7 ° of JP-A-61-239248, metal-free phthalocyanine pigment of JP-B-49-4338, and copper phthalocyanine of JP-A-57-163239. Pigments, vanadyl phthalocyanine pigments of JP-A-57-148747, perylene pigments of JP-A-49-128734, condensed polycyclic pigments of JP-A-47-18544, and bisazo pigments of JP-A-1-150145. is there. As the binder resin, polystyrene, silicone resin, polycarbonate resin, acrylic resin, methacrylic resin, polyester, vinyl polymer, cellulose resin, butyral resin, silicone modified butyral resin, alkyd resin and the like can be used.

The thickness of the charge generation layer is preferably about 0.01 to 10 μm, particularly preferably 0.05 to 2 μm.

A charge transport layer is formed on the charge generation layer. The charge transport layer comprises a compound represented by the general formulas [A] to [G] and a binder resin,
A coating solution containing the compounds represented by the general formulas [A] to [G], a binder resin, and a suitable solvent as main components is applied onto the charge generation layer by an applicator, a bar coater, a dip coater, or the like. Formed by. In this case, the mixing ratio of various compounds and the binder resin is preferably 1: 100 to 100: 1, and particularly preferably 1:20 to 20: 1.

As the charge transport material and the binder resin used in the charge transport layer, any known materials can be used. For example, as the binder resin, acrylonitrile-butadiene copolymer, styrene-butadiene copolymer, vinyltoluene-styrene copolymer, styrene-modified alkyd resin, silicone-modified alkyd resin, soybean oil-modified alkyd resin, vinylidene chloride-vinyl chloride Resin, polyvinyl butyral, nitrated polystyrene, polymethylstyrene, polyisoprene, polyester, phenol resin, Kent resin, polyamide, polycarbonate, polythiocarbonate, polyacrylate, polyhaloacrylate, vinyl acetate resin, polystyrene,
Examples thereof include polyallyl ether, polyvinyl acrylate, polysulfone and polymethacrylate. Among them, biphenyl Z type polycarbonate is particularly preferable. or,
An ambipolar photoreceptor may be prepared by adding an electron donating substance to the charge transport layer.

Further, an antioxidant or a radical trapping agent may be added to the charge transport layer.

The thickness of the charge transport layer is preferably 2 to 100 μm, particularly preferably 5 to 50 μm.

In the electrophotographic photosensitive member of the present invention,
A barrier layer may be provided on the conductive support. The barrier layer is
It is effective in preventing the injection of unnecessary charges from the conductive support and has the effect of improving the image quality. Materials for forming the barrier layer include metal oxide such as aluminum oxide, acrylic resin, phenol resin, polyester resin, polyurethane and the like. The barrier layer may be provided on the adhesive layer or may be provided on the upper side.

[0105]

EXAMPLES Next, the present invention will be specifically described by way of examples.

In the examples described below, the compounds represented by the general formulas [A] to [G] according to the present invention are classified into Examples A to G, and each group includes; (I) Sensitivity evaluation ( Evaluation 1) ... Examples 1 to 10, Comparative Example (1) (II) Durability Evaluation (Evaluation 2) ... Examples 11 to 20, Comparative Example (2) (III) Image Quality Evaluation (Evaluation 3) ... Examples 21 to 30 and Comparative Example (3), except that the compounds according to the present invention are different in each group,
The samples of Examples and Comparative Examples having exactly the same shape, the same kind, and the same size are assembled. The comparative examples of each group are the same for each evaluation.

(I) Evaluation of Sensitivity Evaluation 1 Electrostatic copying paper test apparatus EPA-8100 for electrophotographic photoreceptor samples obtained in Example 1 and Comparative Example (1).
(Kawaguchi Electric Co., Ltd.) is used to charge to + 800V and 10 lu
The white light of x was exposed, and the exposure amount until the surface potential was halved was determined and used as the sensitivity. The results are shown in (I) of Tables 1 to 7.

Examples 1 to 10 A 0.5 μm thick intermediate layer made of polyamide resin “CM8000” (manufactured by Toray Industries, Inc.) was provided on a PET film on which aluminum was vapor-deposited, and a perylene pigment C shown in “Chemical Formula 60” was formed thereon.
GM-1 (1 part), polyvinyl butyral resin "S-REC BMS" (manufactured by Sekisui Chemical Co., Ltd.) 0.2 part, and methyl ethyl ketone (50 parts) as a dispersion medium were dispersed using a sand mill to apply a solution using a wire bar to form a film having a thickness of 0.3 μm. A charge generation layer was formed. Then, 1 part of the exemplified compound shown in each (I) of Tables 1 to 7 and a polycarbonate resin "Iupilon Z-20"
0 "(manufactured by Mitsubishi Gas Chemical Co., Inc.) is dissolved in 10 parts of THF,
A charge transport layer having a film thickness of 20 μm was formed by blade coating on the charge generation layer.

Comparative Example (1) Instead of the exemplified compound, the comparative compound CTM shown in "Chemical Formula 60"
A comparative sample was prepared in the same manner as in Example 1 except that (1) was used.

(II) Durability Evaluation Evaluation 2 The electrophotographic photosensitive member samples obtained in Example 11 and Comparative Example (2) were subjected to the following test with a U-1017 remodeling machine manufactured by Konica Corporation at the initial stage and after copying 10,000 sheets. The measured value was evaluated. The results are shown in Tables 1 to 7 (II).

Vb: Black part potential, Vw: White part potential,
Vr: Residual potential Examples 11 to 20 A 0.5 μm-thick intermediate layer made of polyamide resin “X-1874M” (manufactured by Daicel Huls) was provided on a PET film on which aluminum was vapor-deposited, and the pigment X type was not formed on the intermediate layer. Metal phthalocyanine (manufactured by Dainippon Ink and Chemicals, Inc.) 1 part, polyvinyl butyral resin "ESREC BX-1" (manufactured by Sekisui Chemical Co., Ltd.) 0.4 parts, methyl isopropyl ketone 5 as a dispersion medium
A liquid in which 0 part was dispersed using a sand mill was applied using a wire bar to form a charge generation layer having a thickness of 0.3 μm. Next, 1 part of each of the (II) exemplified compounds in Tables 1 to 7 and 1.5 parts of a polycarbonate resin "Iupilon Z-200" (manufactured by Mitsubishi Gas Chemical Co., Inc.) were dissolved in 10 parts of THF, and blade-coated on the charge generation layer to form a film. A charge transport layer having a thickness of 20 μm was formed.

Comparative Example (2) Comparative compound CTM shown in “Chemical Formula 60” in place of the exemplified compound
A comparative sample was prepared in the same manner as in Example 11 except that (2) was used.

(III) Image Quality Evaluation Evaluation 3 With respect to the electrophotographic photoreceptor samples obtained in Example 21 and Comparative Example (3), a modified machine of digital copy “Konica 9028” manufactured by Konica Corporation (charge polarity: positive, reverse) Image development was performed by (developing). These samples were then placed at low temperature (10
(° C.) environment was left for 1 month, and then images were reproduced again under the same conditions. The black spots on the white background portion of these copied images were evaluated. The results are shown in Tables 1 to 7 (III).

The evaluation of black spots was carried out by measuring the size and number of black spots using an image analyzer "Omnicon 300 type" (manufactured by Shimadzu Corp.), and the number of black spots of φ (diameter) of 0.05 mm or more was 1
This was done by determining how many were present per cm ² . The criteria for evaluating the black spots are as shown below. It should be noted that if the result of the black spot determination is ⊚ or ◯, it is practical, but if it is Δ, it is not suitable for practical use, and if it is ×, it is not suitable for practical use.

Number of black spots of φ0.05 mm or more (pieces / cm ² ) Black spot determination 0 ◎ 1-3 ○ 4-10 △ 11 or more × Examples 21-30 Polyamide resin “CM8000” on a cylindrical aluminum substrate (Manufactured by Toray Industries, Inc.), an intermediate layer having a thickness of 0.5 μm is provided, and a Bragg angle 2θ of 9.5 °, 24.1 °, and 27.
1 part of titanine phthalocyanine having a peak at 2 °, 0.5 part of silicone-butyral resin, 50 parts of methyl isopropyl ketone as a dispersion medium were dispersed using a sand mill to form a charge generation layer having a thickness of 0.3 μm by dip coating. . Next, 1 part of the exemplified compound shown in each (III) of Tables 1 to 7 and 1.5 parts of a polycarbonate resin "Iupilon Z-200" (manufactured by Mitsubishi Gas Chemical Co., Inc.) were dissolved in 10 parts of THF, and dip-coated on the charge generation layer. A charge transport layer having a thickness of 20 μm was formed.

Comparative Example (3) Instead of the exemplified compound, the comparative compound CTM shown in “Chemical Formula 60”
A comparative sample was prepared in the same manner as in Example 21 except that (3) was used.

[0117]

[Chemical 60]

[0118]

[Table 1]

[0119]

[Table 2]

[0120]

[Table 3]

[0121]

[Table 4]

[0122]

[Table 5]

[0123]

[Table 6]

[0124]

[Table 7]

As is clear from the above tables, the electrophotographic photoreceptor using the charge transport material of the present invention has higher sensitivity and is more repetitive than the charge photographic photoreceptor using the conventional charge transport material. The characteristics of the photoconductor during use are stable, and
It can be seen that the occurrence of image defects is extremely small even after storage at low temperature.

[0126]

The compound of the present invention has an electron transporting ability and is practical, that is, high sensitivity, low residual potential, good image retention,
A positive charging photoreceptor can be provided.

[Brief description of drawings]

FIG. 1 is a cross-sectional view of an exemplary embodiment of a photoconductor of the present invention.

[Explanation of symbols]

 1 Conductive Support 2 Charge Generation Layer (CGL) 3 Charge Transport Layer (CTL) 4 Photosensitive Layer 5 Intermediate Layer 6 Layer Containing Carrier Transport Material 7 Carrier Generation Material

Claims (14)

[Claims] 1. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [A]. [Chemical 1] [In the above general formula [A], l, m, and n are l ≧ 0, m
Represents an integer of ≧ 0, n ≧ 1, and when l = 0, m ≧ 2, l ≧
When 1, m ≧ 1, and when l ≧ 2, m ≧ 0. R _A is nitro, OH, halogen, CF ₃ , or an optionally substituted alkyl, alkoxy, aryl, aralkyl, or alkylamino group and CONH ₂ , COOR _A ′, CONHR _A ′, CON
(R _A ′) ₂ and COR _A ′ are represented, and R _A ′ is an alkyl, aryl, or aralkyl group which may have a substituent.
When n ≧ 2, R _A may be the same or different. ] 2. The electrophotographic photosensitive member according to claim 1, wherein the compound represented by the general formula [A] is a compound represented by the following general formula [a]. [Chemical 2] [In the above general formula [a], l and m are synonymous with the general formula [A], and p is an integer of p ≧ 0. Also R _1A , R _2A
Represents an optionally substituted alkyl group, cyano group or halogen atom. ] 3. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [B]. [Chemical 3] [In the above general formula [B], l, m, and n are l ≧ 1, m
Represents an integer of ≧ 1 and n ≧ 1. R _B is nitro, OH, halogen, CF ₃ or an optionally substituted alkyl, alkoxy, aryl, aralkyl or alkylamino group, and CONH ₂ , COOR _B ′, CONHR _B ′, CON (R _B ′) ₂ and COR _B ′ are represented, and R _B ′ is an alkyl, aryl, or aralkyl group which may have a substituent. When n ≧ 2, R
_B may be the same or different. Y _B represents CN and CF ₃ . ] 4. The electrophotographic photosensitive member according to claim 3, wherein the compound represented by the general formula [B] is a compound represented by the following general formula [b]. [Chemical 4] [In the above general formula [b], l and m have the same meanings as in the general formula [B], and p is an integer of p ≧ 0. Also R _1B and R _2B
Represents an optionally substituted alkyl group, cyano group or halogen atom. ] 5. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [C]. [Chemical 5] [In the above general formula [C], l, m, and n are l ≧ 1, m
Represents an integer of ≧ 0, n ≧ 1, and when l = 1, m ≧ 1, l =
When 2, m ≧ 0. _RC is nitro, OH, halogen, C
F ₃ , each optionally substituted alkyl, alkoxy, aryl, aralkyl, alkylamino group and CONH ₂ , C
OOR _C ′, CONHR _C ′, CON (R _C ′) ₂ , COR _C ′,
R _C ′ represents an alkyl, aryl or aralkyl group which may have a substituent. When n ≧ 2, R may be the same or different. X _C is OCOR _C ′, COOR _C ′, CONH
R _C ′, COR _C ′, CHO, CON (R _C ′) ₂ , Y _C represent CN, NO ₂ , halogen, CF ₃ , COOH, SO ₂ NH ₂ , SOR _C ′ and SO ₂ R _C ′. ] 6. The electrophotographic photosensitive member according to claim 5, wherein the compound represented by the general formula [C] is a compound represented by the following general formula [c]. [Chemical 6] [In the above general formula [c], X _c , Y _c and 1, m have the same meanings as in the general formula [C], and p is an integer of p ≧ 0. R _1c and R _2c represent an alkyl group which may have a substituent, a cyano group or a halogen atom. ] 7. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [D]. [Chemical 7] [In the general formula [D], l, m, and n are l ≧ 1, m
Represents an integer of ≧ 0, n ≧ 1, and when l = 1, m ≧ 1, l =
When 2, m ≧ 0. R _D is nitro, OH, halogen, C
F ₃ , an optionally substituted alkyl, alkoxy,
Aryl, aralkyl, alkylamino groups and CONH
₂ , COOR _D ′, CONHR _D ′, CON (R _D ′) ₂ and COR _D ′ represent each group, and R _D ′ represents each optionally substituted alkyl, aryl or aralkyl group. When n ≧ 2, R _D may be the same or different. X _D is COOH, SO ₂ NH ₂ , SOR
_D ′, SO ₂ R _D ′ and Y _D represent CN, NO ₂ , halogen and CF ₃ . ] 8. The electrophotographic photosensitive member according to claim 7, wherein the compound represented by the general formula [D] is a compound represented by the following general formula [d]. [Chemical 8] [In the general formula [d], X _D , Y _D and 1, m have the same meanings as in the general formula [D], and p is an integer of p ≧ 0. R _1D and R _2D represent an alkyl group which may have a substituent, a cyano group or a halogen atom. ] 9. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [E]. [Chemical 9] [In the general formula [E], l, m, and n are l ≧ 1, m
Represents an integer of ≧ 0, n ≧ 1, and when l = 1, m ≧ 1, l =
When 2, m ≧ 0. R _E is nitro, OH, halogen, C
F ₃ , an optionally substituted alkyl, alkoxy,
Aryl, aralkyl, alkylamino groups and CONH
₂ , COOR _E ′, CONR _E ′, CON (R _E ′) ₂ , COR _E ′, each R _E ′ represents an optionally substituted alkyl, aryl, or aralkyl group. When n ≧ 2, R _E may be the same or different. X _E is a halogen atom, Y _E
Represents CN, NO ₂ and CF ₃ . ] 10. The electrophotographic photosensitive member according to claim 9, wherein the compound represented by the general formula [E] is a compound represented by the following general formula [e]. [Chemical 10] [In the above general formula [e], X _E , Y _E and 1, m have the same meanings as in the general formula [E], and p is an integer of p ≧ 0. R _1E and R _2E represent an alkyl group which may have a substituent, a cyano group or a halogen atom. ] 11. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [F]. [Chemical 11] [In the above general formula [F], l, m, and n are l ≧ 2, m
Represents an integer of ≧ 1 and n ≧ 1. R _F is nitro, OH, halogen, CF ₃ or an optionally substituted alkyl, alkoxy, aryl, aralkyl or alkylamino group, and CONH ₂ , COOR _F ′, CONHR _F ′, CON (R _F ′) ₂ and COR _F ′ are represented, and R _F ′ is alkyl, aryl and aralkyl which may have a substituent. When n ≧ 2, R
_F may be the same or different. R _OF is an alkyl, aryl or aralkyl group which may have a substituent, X _F
Is CN, NO ₂ , halogen, CF ₃ , CHO, COOH, SO ₂ NH ₂ , SO
R _F ′ and SO ₂ R _F ′, OCOR _F ′, COOR _F ′, CONHR _F ′, CO
Represents R _F ′. ] 12. The electrophotographic photosensitive member according to claim 11, wherein the compound represented by the general formula [F] is a compound represented by the following general formula [f]. [Chemical 12] [In the above general formula [f], X _F , R _OF and 1, m have the same meanings as in the general formula [F], and p is an integer of p ≧ 0.
R _1F and R _2F represent an alkyl group which may have a substituent, a cyano group or a halogen atom. ] 13. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula [G]. [Chemical 13] [In the above general formula [G], l, m, and n are l ≧ 0, m
It represents an integer of ≧ 2 and n ≧ 1. X _G is nitro, OH, halogen, CN, or an optionally substituted aryl, aralkyl, N (R _G ′) ₂ , OR _G ′, OCOR _G ′, COOR _G ′, CONHR _G ′, C
Represents ON (R _G ′) ₂ , COR _G ′, SOR _G ′ and SO ₂ R _G ′ groups,
R _G ′ represents an alkyl, aryl or aralkyl group which may have a substituent. When n ≧ 2, X _G may be the same or different. Y _G represents an alkyl group which may have a substituent. ] 14. The electrophotographic photosensitive member according to claim 13, wherein the compound represented by the general formula [G] is a compound represented by the following general formula [g]. [Chemical 14] [In the general formula [g], l, m, and n are l = 0, m
Represents an integer of ≧ 3 and n ≧ 1. X _G is nitro, halogen, C
N, aryl which may have a substituent, COOR _G ′, OCOR
_G ′, CONHR _G ′, CON (R _G ′) ₂ , COR _G ′,
R _G ′ represents an alkyl, aryl or aralkyl group which may have a substituent. Others are synonymous with general formula [G]. ]