JP3281906B2 - Electrophotographic photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member, and more particularly, to an electrophotographic photosensitive member containing a specific compound in a photosensitive layer.

[0002]

2. Description of the Related Art Conventionally, inorganic materials such as selenium, cadmium sulfide, and zinc oxide have been used as a photoconductive material of a photoreceptor used in an electrophotographic system.
The term "electrophotographic method" as used herein generally means that a photoconductive photoreceptor is first charged in a dark place, for example, by corona discharge, and then subjected to image exposure to selectively dissipate only the charges in the exposed portions and to reduce static electricity. An electrostatic latent image was obtained, and the latent image portion was developed and visualized with electro-detection fine particles (toner) composed of a coloring material such as a dye or a pigment and a binder such as a polymer substance to form an image. This is one of the image forming methods.

The basic characteristics required of a photoreceptor in such an electrophotographic method include (1) charging to an appropriate potential in a dark place, (2) little electric charge dissipation in a dark place, and ( 3) Charges can be quickly dissipated by light irradiation.

[0004] The above-mentioned inorganic substances have many advantages and also have various disadvantages. For example, selenium, which is widely used at present, satisfies the above conditions (1) to (3), but the production conditions are difficult, the production cost is high, there is no flexibility, and the selenium is processed into a belt shape. It also has drawbacks in that it is difficult to handle, and is sensitive to heat and mechanical shocks, and requires careful handling. Cadmium sulfide and zinc oxide are used as photoreceptors by dispersing them in a resin as a binder.However, due to mechanical defects such as smoothness, hardness, tensile strength, and abrasion resistance, they are repeatedly used as they are. Can not be used.

In recent years, electrophotographic photoreceptors using various organic substances have been proposed to eliminate the disadvantages of these inorganic substances, and some of them have been put to practical use. For example, a photoreceptor comprising poly-N-vinylcarbazole and 2,4,7-trinitrofluoren-9-one (U.S. Pat.
84237), a photoreceptor obtained by sensitizing poly-N-vinylcarbazole with a pyrylium salt-based dye (described in JP-B-48-25658), and a photoreceptor containing an organic pigment as a main component (see JP-B-48-25658). JP-A-47-37543), a photoreceptor containing a eutectic complex composed of a dye and a resin as a main component (described in JP-A-47-10735), and dye-sensitized triphenylamine compound. (US Pat. No. 3,180,730), a photoreceptor using an amine derivative as a charge transport material (JP-A-57-195254), and poly-N-vinylcarbazole and an amine derivative as charge transport materials Photoreceptor used (Japanese Patent Laid-Open No. 58-11 / 1983)
55, a photoconductor using a benzidine compound among polyfunctional tertiary amine compounds as a photoconductive material (US Pat. No. 3,265,496, JP-B-39-11546, JP-A-53-27033). ). Although these photoreceptors have excellent properties and are considered to be of high practical value, in electrophotography, considering various requirements for photoreceptors, these requirements are still insufficient. In fact, it is not possible to obtain anything satisfying the above conditions.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a photoreceptor which can solve the above-mentioned various disadvantages of the conventional photoreceptor and can sufficiently satisfy the conditions required in electrophotography. It is in. It is a further object of the present invention to provide an electrophotographic photoreceptor which is easy to manufacture, relatively inexpensive, and has excellent durability.

[0007]

According to the present invention, a photosensitive layer containing at least one diamine compound represented by the following general formula (I) as an active ingredient is provided on a conductive support. Is provided.

Embedded image (In the formula, R ¹ , R ² and R ³ each independently represent a substituted or unsubstituted alkyl group or aryl group, and R ² and R ³ are pyrene.
Excludes the case of a nyl group . R ⁴ represents a hydrogen atom, an alkyl group or an alkoxy group, and n represents an integer of 1 to 3. −
X- represents a substituted or unsubstituted arylene group or a divalent group of a heterocyclic group, and 2,9 -dihydrophenanthrene 2
Except when it is a divalent group or a divalent group of phenanthrene.
Good. )

In the present invention, the diamine compound represented by the above general formula (I) to be contained in the photosensitive layer is a novel compound, which is generally an N-alkyl substitution reaction or N-aryl substitution of the corresponding amino compound. Substitution reaction and N
Synthesized by a combination with a pyrenyl substitution reaction.
Corresponding halides are generally used for the alkylation, arylation and pyrenylation reactions, and the arylation reaction is described in Ull.
A general method is to use a mann reaction.

When the Ullmann reaction is carried out, N, N-dimethylformamide, nitrobenzene, dimethylsulfoxide, dichlorobenzene and the like are used as a solvent. Potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydride and the like are used as the basic compound as the deoxidizing agent. The reaction temperature is usually from 160 to 25.
The reaction is performed at 0 ° C. in the presence or absence of a solvent. If the reactivity is still worse, a higher temperature reaction may be performed using an autoclave or the like. In some cases, it is usually more advantageous to carry out the reaction by adding a catalyst such as copper powder or copper oxide or copper halide.

In the general formula (I), when R ¹ , R ² and / or R ³ is an aryl group, specific examples include non-condensed hydrocarbon groups such as phenyl, biphenylyl and terphenylyl groups, and condensed polycyclic carbons. And a hydrogen group.

The fused polycyclic hydrocarbon group preferably has 18 or less carbon atoms forming a ring, for example, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,
Heptalenyl group, biphenylenyl group, as-indacenyl group, fluorenyl group, s-indacenyl group, acenaphthylenyl group, preyadenyl group, acenaphthenyl group, phenalenyl group, phenanthryl group, anthryl group, fluoranthenyl group, acephenanthrenyl group, Examples include an aceanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a naphthacenyl group.

Further, in the general formula (I),

Embedded image When it is an arylene group, specific examples include divalent groups of monocyclic hydrocarbon compounds such as benzene, diphenyl ether, polyethylene glycol diphenyl ether, diphenyl thioether and diphenyl sulfone, or biphenyl, polyphenyl, diphenyl alkane, diphenyl alkene, diphenyl alkyne, triphenyl Divalent groups of non-condensed polycyclic hydrocarbon compounds such as phenylmethane, distyrylbenzene, 1,1-diphenylcycloalkane, polyphenylalkane, and polyphenylalkene, or condensed polycyclic hydrocarbons described as specific examples of R ¹ Examples include a divalent group of a compound or a divalent group of a ring-assembled hydrocarbon compound such as 9,9-diphenylfluorene. When it is a heterocyclic group, specific examples include divalent groups such as carbazole, dibenzofuran, dibenzothiophene, oxadiazole, and thiadiazole.

When R ¹ , R ² and / or R ³ is an aryl group;

Embedded image Represents a divalent group of an arylene group or a heterocyclic group, and may have the following substituents.

(1) halogen atom, cyano group, nitro group (2) alkyl group, preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group substituted with a phenyl group, a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like.

(3) alkoxy group (-OR ⁵ ); R ⁵ represents an alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. This is C ₁
Alkoxy group -C _4, alkyl group, or a halogen atom C ₁ -C ₄ may contain a substituent group. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2
-Naphthyloxy group and the like.

(5) An alkylmercapto group or an arylmercapto group; specific examples include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group.

[0018] Represents an alkyl group or an aryl group, and an aryl group
For example, phenyl group, biphenylyl group or naphthyl
And these include C₁~ C_FourAn alkoxy group of C
₁~ C_FourWith an alkyl group or a halogen atom as a substituent
May be contained. R⁶And R⁷May form a ring together
No. And form a ring together with the carbon atom on the aryl group
Is also good. ) Specifically, amino group, diethylamino group, N-methyl
-N-phenylamino group, N, N-diphenylamino
Group, N, N-di (p-tolyl) amino group, dibenzyl
Amino group, piperidino group, morpholino group, euroridyl group
And the like. (7) a methylenedioxy group or a methylenedithio group
An alkylenedioxy group or an alkylenedithio group;
I can do it. In the general formula (I), R¹, R^Two, R^Threeas well as
R^FourA specific example of when is an alkyl group is (2)
The same ones as defined are included.

Hereinafter, representative examples of the diamine compound represented by the general formula (I) are shown.

[0020]

[Table 1- (1)]

[0021]

[Table 1- (2)]

[0022]

[Table 1- (3)]

[0023]

[Table 1- (4)]

[0024]

[Table 1- (5)]

[0025]

[Table 1- (6)]

The photoreceptor of the present invention comprises one or more of the above-mentioned diamine-based compounds as the photosensitive layer 2 (2 ′,
2 ", 2""or2""), which are shown in FIG. 1, FIG. 2, FIG. 3, FIG. 4 or FIG. 5 depending on how these diamine compounds are applied. It can be used as follows.

The photosensitive member in FIG. 1 is obtained by forming a diamine compound, a sensitizing dye and a binder (binder resin) on a conductive support 1.
The photosensitive layer 2 is provided. The diamine compound here acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation are performed via the diamine compound. However, since the diamine compound has little absorption in the visible region of light, it is necessary to sensitize by adding a sensitizing dye having absorption in the visible region for the purpose of forming an image with visible light. is there.

The photoreceptor shown in FIG. 2 comprises a conductive support 1 and a photosensitive layer 2 'in which a charge generating substance 3 is dispersed in a charge transport medium 4 comprising a diamine compound and a binder. It is. The diamine compound here forms a charge transport medium together with a binder (or a binder and a plasticizer), while the charge generating substance 3 (a charge generating substance such as an inorganic or organic pigment) generates a charge carrier. . In this case, the charge transport medium 4 is mainly responsible for receiving and transporting charge carriers generated by the charge generating substance 3. In this photoreceptor, the basic condition is that the charge generation substance and the diamine-based compound do not overlap in the absorption wavelength region mainly in the visible region. This is because it is necessary to transmit light to the surface of the charge generating material 3 in order to efficiently generate charge carriers in the charge generating material 3. The diamine compound represented by the general formula (I) hardly absorbs in the visible region, and generally absorbs light in the visible region to generate a charge carrier.
The feature is that it works as a charge transport material particularly effectively when combined with.

The photosensitive member shown in FIG. 3 is a photosensitive layer 2 'comprising a conductive support 1 and a charge generating layer 5 mainly composed of a charge generating substance 3 and a charge transport layer 4 containing a diamine compound. 'Is provided. In this photoconductor,
The light transmitted through the charge transport layer 4 reaches the charge generation layer 5, where charge carriers are generated in the region.
Receives the charge carrier injection and transports the charge carrier. The charge carriers required for light attenuation are generated by the charge generating substance 3, and the charge carriers are transported by the charge transport layer 4 (mainly a diamine-based compound). Works). Such a mechanism is the same as that described for the photoconductor shown in FIG.

The photosensitive member in FIG.
And the charge transport layer 4 containing the diamine-based compound is reversed in the stacking order, and the mechanism of generation and transport of the charge carriers can be the same as described above. In this case, a protective layer 6 can be provided on the charge generation layer 5 in the fifth manner in consideration of mechanical strength.

In order to actually manufacture the photoreceptor of the present invention, FIG.
In the photoreceptor shown in (1), one or more diamine compounds are dissolved in a solution in which a binder is dissolved, and a solution is prepared by adding a sensitizing dye thereto. What is necessary is just to apply | coat on top and dry, and to form the photosensitive layer 2.

The thickness of the photosensitive layer is 3 to 50 μm, preferably 5 to 20 μm. The amount of the diamine compound in the photosensitive layer 2 is 30 to 70% by weight, preferably about 50% by weight, and the amount of the sensitizing dye in the photosensitive layer 2 is 0.1 to 5% by weight, preferably 0 to 5% by weight. 0.5 to 3% by weight. Examples of sensitizing charges include triarylmethane dyes such as brilliant green, Victoria Blue B, methyl violet, crystal violet, and acid violet 6B, rhodamine B, rhodamine 6G, rhodamine G extra, eosin S, erythrosin, rose bengal, and fluorescein. Such as xanthene dyes, thiazine dyes such as methylene blue, cyanine dyes such as cyanine, 2,6-diphenyl-4- (N, N-dimethylaminophenyl) thiapyrylium perchlorate, and benzopyrylium salts (Japanese Patent Publication No. Sho 48) 25658)) and the like. These sensitizing dyes may be used alone or in combination of two or more.

In order to produce the photoreceptor shown in FIG. 2, fine particles of the charge generating substance 3 are dispersed in a solution in which one or more diamine compounds and a binder are dissolved.
This may be applied onto the conductive support 1 and dried to form the photosensitive layer 2 '.

The thickness of the photosensitive layer 2 'is 3 to 50 μm, preferably 5 to 20 μm. The amount of the diamine compound in the photosensitive layer 2 'is 10 to 95% by weight, preferably 3 to 95% by weight.
0 to 90% by weight, and the amount of the charge generating substance 3 in the photosensitive layer 2 'is 0.1 to 50% by weight, preferably 1 to 50% by weight.
20% by weight. Examples of the charge generating substance 3 include inorganic pigments such as selenium, selenium-tellurium, cadmium sulfide, cadmium sulphide-selenium, and α-silicon, and examples of the organic pigments include CI Pigment Blue 25 (color index CI 21180) and CI Pigment Red 41. (CI2200), CI Acid Red 52 (CI 45100), CI Basic Red 3 (CI45210), an azo pigment having a carbazole skeleton (described in JP-A-53-95033), and an azo pigment having a distyrylbenzene skeleton (see Kaisho 53-13
No. 3445), an azo pigment having a triphenylamine skeleton (described in JP-A-53-132347), and an azo pigment having a dibenzothiophene skeleton (JP-A-54-132347).
21728), an azo pigment having an oxadiazole skeleton (described in JP-A-54-12742), and an azo pigment having a fluorenone skeleton (described in JP-A-54-12742).
No. 22834), an azo pigment having a bisstilbene skeleton (described in JP-A-54-17733), and an azo pigment having a distyryloxadiazole skeleton (described in JP-A-54-2129) And azo pigments having a distyrylcarbazole skeleton (JP-A-54-14)
Azo pigments such as C.I. Pigment Blue 16 (CI 74100), such as C.I.
(CI73410), sea butt die (CI73
030) and other indigo pigments, Argo Scarlet B
(Manufactured by Bayer AG) and perylene pigments such as Indance Scarlet R (manufactured by Bayer AG).
These charge generating substances may be used alone or in combination of two or more.

Further, in order to produce the photoreceptor shown in FIG. 3, a charge generating substance is vacuum-deposited on the conductive support 1 or more, or a fine particle 3 of the charge generating substance is dissolved in a binder if necessary. Coating and drying, and further, if necessary, surface finishing and film thickness adjustment by a method such as buffing, and the like.
Is formed, and a solution in which one or more diamine-based compounds and a binder are dissolved is applied thereon and dried to form the charge transport layer 4. Here, the charge generation material used for forming the charge generation layer 5 is the same as that described in the description of the photosensitive layer 2 '.

The thickness of the charge generation layer 5 is 5 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer 4 is 3 to 50 μm.
μm, preferably 5 to 20 μm is suitable. In the type in which the charge generation layer 5 has the fine particles 3 of the charge generation layer material dispersed in a binder, the ratio of the fine particles 3 of the charge generation material to the charge generation layer 5 is preferably 10 to 95% by weight. Is about 50 to 90% by weight. The charge transport layer 4
Is 10 to 95% by weight, preferably 3% by weight.
0 to 90% by weight. To prepare the photoreceptor shown in FIG. 4, a solution in which a diamine-based compound and a binder are dissolved is applied on the conductive support 1 and dried to form the charge transport layer 4. The charge generation layer 5 may be formed by applying a dispersion of fine particles of the charge generation layer material in a solvent in which a binder is dissolved, if necessary, by a method such as spray coating and drying. The amount ratio of the charge generation layer or the charge transport layer is the same as that described in FIG. The photoreceptor shown in FIG. 5 can be prepared by further forming a protective layer 6 on the thus-obtained photoreceptor charge generation layer 5 by a method such as spray coating. As the resin used here, a binder described later can be used.

In the production of any of these photoconductors, a metal plate or a metal foil such as aluminum, a plastic film on which a metal such as aluminum is deposited, or a paper subjected to a conductive treatment is used for the conductive support 1. Can be Examples of the binder include condensation resins such as polyamide, polyurethane, polyester, epoxy resin, polyketone, and polycarbonate; and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, and polyacrylamide. All insulating and adhesive resins can be used. If necessary, a plasticizer is added to the binder. Examples of such a plasticizer include halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, and dibutylphthalate.

Further, the photosensitive member obtained as described above may be provided with an adhesive layer or a barrier layer between the conductive support and the photosensitive layer, if necessary. Materials used for these layers include polyamide, nitrocellulose,
Aluminum oxide and the like, and the film thickness is preferably 1 μm or less. To make a copy using the photoreceptor of the present invention,
After the photosensitive surface is charged and exposed, development is performed and, if necessary, transfer to paper or the like. The photoreceptor of the present invention has excellent advantages such as high sensitivity and high flexibility.

[0039]

The present invention will be described below with reference to examples. In the following examples, all parts are parts by weight.

[Synthesis of Compound of General Formula (I)] Production Example (Compound No. 27) 7.63 g (30 mmol) of N-acetyl-o-tolidine
l), 21.8 g of p-iodotoluene (100 mmol)
l), 0.63 g (10 mmol) of copper powder and 14.7 g (150 mmol) of anhydrous potassium carbonate were added to nitrobenzene 5
The mixture was heated and stirred at 200 ° C. for 10 hours in 0 ml. After completion of the heating and stirring, an aqueous solution obtained by dissolving 5.6 g (1000 mmol) of 96% potassium hydroxide in 50 ml of isoamyl alcohol and 20 ml of water was added, and the mixture was hydrolyzed at 120 ° C. for 8 hours. After distilling off isoamyl alcohol and nitrobenzene by steam distillation, the mixture was extracted with 200 ml of toluene, the insolubles were filtered, washed with water, dried and concentrated. The obtained crystals were purified by column chromatography (carrier: silica gel, eluent: toluene / n-hexane = 1/2) to give N, N, N'-tri (p-tolyl) -o-tolidine 10 9.9 g (yield = 74%, melting point = 141.0-
143.0 ° C). Next, N, N, N'-tri (p
-Tolyl) -o-tolidine 3.93 g (10 mmo
l), 4.10 g of 1-iodopyrene (12.5 mmol)
l), 0.19 g (3 mmol) of copper powder and 3.92 g (40 mmol) of potassium carbonate in 50 ml of nitrobenzene
And stirred at 200 ° C. for 7 hours. After the completion of the heating and stirring, the reaction product was extracted into 100 ml of toluene, which was concentrated to obtain a yellow oil. Column chromatography (carrier: silica gel, eluent: toluene / n-hexane = 1)
/ 2) to give N- (1-pyrenyl) -N,
3.11 g of N ', N'-tri (p-tolyl) -o-tolidine (Compound No. 27) (yield = 39%, melting point = 23)
2.0-233.5 ° C). Elemental analysis value was C ₅₁ H
₄₂ N ₂ was as follows. C (%) H (%) N (%) Actual value 89.70 6.20 4.10 Theoretical value 90.05 6.44 3.89 Other diamine compounds were synthesized in the same manner as described above.

Example 1 76 parts of Diane Blue (C.I. Pigment Blue 25, CI21180), 1260 parts of a 2% tetrahydrofuran solution of a polyester resin (Vylon 200, manufactured by Toyobo Co., Ltd.) and 3,700 parts of tetrahydrofuran were used as a charge generating material in a ball mill. The resulting dispersion was applied using a doctor blade on the aluminum surface of a conductive base made of a polyester base on which aluminum was deposited, and was naturally dried to form a charge generation layer having a thickness of about 1 μm. . On the other hand, as the charge transport substance, Compound Specific Example No. After mixing and dissolving 2 parts of the diamine-based compound of No. 6, 2 parts of a polycarbonate resin (Panlite K1300, manufactured by Teijin Ltd.) and 16 parts of tetrahydrofuran, a solution is formed on the charge generation layer using a doctor blade. It is applied and dried at 80 ° C. for 2 minutes and then at 120 ° C. for 5 minutes to form a charge transport layer having a thickness of about 20 μm. 1 was created.

Examples 2 to 23 Charge-generating substances and charge-transporting substances (diamine compounds)
Was changed to that shown in Table 2 in exactly the same manner as in Example 1. 2 to 23 were prepared. Table 2 shows the results.

[0043]

[Table 2- (1)]

[0044]

[Table 2- (2)]

[0045]

[Table 2- (4)]

Example 24 Selenium was vacuum-deposited to a thickness of about 1 μm on an aluminum plate having a thickness of about 300 μm to form a charge generation layer. Next, No. 6 diamine compound, polyester resin (Polyester Adhesive 49000 manufactured by DuPont)
3 parts and 45 parts of tetrahydrofuran are mixed and dissolved to prepare a charge transport layer forming solution, which is applied on the above-described charge generation layer (selenium vapor deposition layer) using a doctor blade, air-dried, and then dried under reduced pressure. Dry to a thickness of about 10μm
Of the photoreceptor No. of the present invention. 2
4 was obtained.

Example 25 A perylene pigment is used instead of selenium

Embedded image To form a charge generation layer (thickness: about 0.6 μm), and a diamine compound No. 1 as a charge transport material.
Photoconductor No. 6 was used in the same manner as in Example 24 except that No. 6 was used. 25 were created.

Example 26 A mixture obtained by adding 158 parts of tetrahydrofuran to 1 part of Diane Blue (same as that used in Example 1) was pulverized and mixed in a ball mill. The photosensitive layer forming liquid obtained by adding 12 parts of the diamine compound of No. 6 and 18 parts of a polyester resin (Polyester Adhesive 49000 manufactured by DuPont) and further mixing the mixture was applied on an aluminum-evaporated polyester film using a doctor blade. Then, the resultant was dried at 100 ° C. for 30 minutes to form a photosensitive layer having a thickness of about 16 μm. 26 was created.

Example 27 On a polyester film substrate on which aluminum was deposited,
The coating liquid for the charge transport layer used in Example 1 was coated with a blade in the same manner as in Example 1, and then dried to form a charge transport layer having a thickness of about 20 μm. Bisazo pigment (P-2) 13.
5 parts, polyvinyl butyral (trade name: XYHL Union Carbide Plastic Co., Ltd.) 5.4 parts, THF 6
After 80 parts and 1020 parts of ethyl cellosolve were pulverized and mixed in a ball mill, 1700 parts of ethyl cellosolve was added and mixed by stirring to obtain a coating liquid for a charge generation layer. This coating solution is spray-coated on the charge transport layer,
After drying for 0 minutes, a charge generation layer having a thickness of about 0.2 μm was formed. Further, a methanol / n-butanol solution of a polyamide resin (trade name: CM-8000, manufactured by Toray) is spray-coated on the charge generation layer, dried at 120 ° C. for 30 minutes, and dried to a thickness of about 0.5 μm. To form the photosensitive member N
o. 27 was created.

The photosensitive member No. 1-27
Using a commercially available electrostatic copying paper tester (type SP428, manufactured by KK Kawaguchi Electric Manufacturing Co., Ltd.), a corona discharge of -6 KV or +6 KV was performed for 20 seconds, and the surface was charged in a dark place for 20 seconds. The potential Vpo (volt) was measured, and then a tungsten lamp light was applied so that the illuminance on the photoreceptor surface became 4.5 lux, and the time (second) until the surface potential became 1/2 of Vpo was obtained. , Exposure amount E
1/2 (look-seconds) was calculated. Table 3 shows the results.

After charging each of the above photoreceptors using a commercially available electrophotographic copying machine, the photosensitive members are irradiated with light through the original drawing to form an electrostatic latent image, and developed using a dry developer. When the obtained image (toner image) was electrostatically transferred onto plain paper and fixed, a clear transfer image was obtained. Similarly, when a wet type developer was used as the developer, a clear transfer image was obtained.

[0052]

[Table 3- (1)]

[0053]

[Table 3- (2)]

[0054]

[Table 3- (3)]

[0055]

The photoreceptor of the present invention is excellent in photosensitive characteristics, has high strength against heat and mechanical shock, and can be manufactured at low cost.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view of a typical electrophotographic photosensitive member according to the present invention, which is enlarged in a thickness direction.

FIG. 2 is a cross-sectional view of another typical electrophotographic photosensitive member according to the present invention, which is enlarged in a thickness direction.

FIG. 3 is a cross-sectional view enlarged in a thickness direction of still another typical electrophotographic photosensitive member according to the present invention.

FIG. 4 is a cross-sectional view enlarged in a thickness direction of another electrophotographic photosensitive member according to the present invention.

FIG. 5 is a cross-sectional view enlarged in a thickness direction of still another electrophotographic photosensitive member according to the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 conductive support 2, 2 ′, 2 ″, 2 ″ ″ photosensitive layer 3 charge generation material 4 charge transport medium or charge transport layer 5 charge generation layer 6 protective layer

──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Masafumi Ota 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Company Limited (72) Inventor Mitsutoshi Anzai 1-4-2 Toranomon, Minato-ku, Tokyo Inside Hodogaya Chemical Industry Co., Ltd. (72) Inventor Yasuo Murakami 1-4-2 Toranomon, Minato-ku, Tokyo Inside Hodogaya Chemical Industry Co., Ltd. (72) Atsushi Takei 1-4, Toranomon, Minato-ku, Tokyo No. 2 Hodogaya Chemical Co., Ltd. (56) References JP-A-5-27460 (JP, A) JP-A-4-323662 (JP, A) JP-A-4-182441 (JP, A) JP Japanese Unexamined Patent Application Publication No. Hei 4-133064 (JP, A) Japanese Unexamined Patent Application Publication No. Hei 2-190863 (JP, A) Japanese Unexamined Patent Application Publication No. Hei 5-58966 (JP, A) Japanese Unexamined Patent Application Publication No. Hei 3-285960 (JP, A) , A) JP-A-2-190864 (JP, A) JP-A-6-89039 (JP, A) JP-A-6-107605 (JP, A) JP-A-5-112509 (JP, A) JP-A-4-186362 (JP, A) JP-A-7-101917 (JP) , A) (58) Fields studied (Int. Cl. ⁷ , DB name) G03G 5/00 CA (STN)

Claims (1)

(57) [Claims] 1. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer containing at least one diamine compound represented by the following general formula (I) as an active ingredient. Embedded image (In the formula, R ¹ , R ² and R ³ each independently represent a substituted or unsubstituted alkyl group or aryl group, and R ² and R ³ are pyrene.
Excludes the case of a nyl group . R ⁴ represents a hydrogen atom, an alkyl group or an alkoxy group, and n represents an integer of 1 to 3. −
X- represents a substituted or unsubstituted arylene group or a divalent group of a heterocyclic group, and 2,9 -dihydrophenanthrene 2
Except when it is a divalent group or a divalent group of phenanthrene.
Good. )