JPS5885439A - Electrophotographic receptor - Google Patents

Abstract

PURPOSE:To raise sensitivity and to lower residual potential, by adding a specified amine deriv. to a photosensitive layer. CONSTITUTION:An amine derivative is represented by general formula (I) or (II) in which R1-R4 are each H, halogen, alkyl, alkoxy, aryl, ayloxy, or amino; R5-R10 are each H, halogen, alkyl, aryl, or cyano; and Ar is an aromatic heterocyclic group, and this derivative is added to a carrier transfer layer formed on a conductive support as a carrier transfer substance, and a carrier generating layer is laminated on this layer to form an electrophotographic receptor. The low mol.wt. org. photoconductor is low in compatibility with a binder, but this deriv. is high in compatibility, stable against heat and light, and superior in carrier transfer performance.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is directed to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor comprising a photosensitive layer made of an organic photoconductive compound.

Conventionally, electrophotographic photoreceptors having a photosensitive layer containing an inorganic photoconductor such as selenium, zinc oxide, or cadmium sulfide as a main component are widely known. However, these are not necessarily satisfactory in terms of properties such as thermal stability, durability, and moisture resistance, and are also toxic, resulting in manufacturing hazards.
There are also problems in handling.

On the other hand, electrophotographic photoreceptors having a photosensitive layer containing an organic photoconductive compound as a main component are relatively easy to manufacture, inexpensive, easy to handle, and generally selenium photoreceptors, etc. It has many advantages, such as superior thermal stability, and has attracted much attention in recent years. Examples of such organic photoconductive compounds include poly-N-vinyl cal-I, a mono-charged material formed by a Lewis acid tochar such as polynitro-9-fluorenone, and an electrophotographic photoreceptor having a photosensitive layer containing a dynamic complex as a main component. has already been put into practical use.

On the other hand, electrophotographic photoreceptors are known that have a 1 m type or dispersion type functionally separated photosensitive layer in which the carrier generation function and the carrier transport function in the photoconductive photosensitive layer are assigned to separate substances, respectively. For example, electrophotographic photoreceptors have been put into practical use that have a photosensitive layer that combines a carrier generation layer made of an amorphous selenium thin layer and a carrier transport layer made of poly-N-vinylcarbazole.

However, since poly-N-vinylcarbazole lacks flexibility, its coating is hard and brittle and prone to cracking and peeling, so electrophotographic photoreceptors using it have poor durability. In addition, if a plasticizer is added to improve this defect, the residual mf level will increase when subjected to the electrophotographic process, and as it is repeatedly used, the residual potential will increase and the copied image will gradually become foggy (5 ).

Furthermore, since a low molecular weight organic photoconductive compound generally has a film-forming ability, it is used in combination with an arbitrary binder. Therefore, it is preferable that the physical properties or electrophotographic properties of the film can be modified to some extent by selecting the type and composition ratio of the binder used, but The types of highly compatible organic photoconductive compounds are limited, and the reality is that there are not many of them that can actually be used in the composition of the photosensitive layer of an electrophotographic photoreceptor.

For example, 2,5-bis(p-diethylaminophenyl) is described in U.S. Pat. No. L189.447.
-1,3,4-oxadiazole has poor compatibility with binders that are usually preferably used as a material for the photosensitive layer of electrophotographic photoreceptors, so it cannot be used with binders such as polyester or polycarbonate. When a photosensitive layer is formed by mixing with oxadiazole in the proportion required to obtain favorable electrophotographic properties, oxadiazole crystals will precipitate at temperatures above 50°C, resulting in poor charge retention, sensitivity, etc. (6) It has the disadvantage that the electrophotographic characteristics deteriorate.

In contrast, the diarylalkane reading conductor described in U.S. Pat. Therefore, should electrophotographic photoreceptors using this be handled with care in a bright room? I need to get rid of it. Furthermore, when used in the construction of the photosensitive layer of a repulsion transfer type electrophotographic photoreceptor in which charging, exposure, and development steps are repeated, the sensitivity of the photosensitive layer gradually decreases and the residual potential increases, resulting in poor durability. It has the disadvantage of being inferior in quality.

As described above, it is true that an organic photoconductive compound having practically preferable characteristics for producing an electrophotographic photoreceptor has not yet been developed.

The object of the present invention is to provide a photosensitive layer comprising a novel organic photoconductive 1M compound having excellent compatibility with a binder, being stable against heat and light, and having excellent carrier transport ability. The object of the present invention is to provide a child photographic photoreceptor.

Another object of the present invention is that the yp-strong
) An object of the present invention is to provide an electrophotographic photoreceptor having a complete photolinkable electrical layer that has excellent stability during repeated use.

Still another object of the present invention is to provide an electrophotographic photoreceptor with high sensitivity and a round residual potential.

Another object of the present invention is that when used as a repetitive transfer type electrophotographic photoreceptor in which charging, irradiation, development, and transfer steps are repeated, fatigue deterioration due to repeated use is small, the characteristics are stable, and the characteristics are stable over time. An object of the present invention is to provide an electrophotographic photoreceptor having excellent durability.

In order to achieve the above object, the present inventors conducted research and discovered that a specific amine derivative was used as a photoreceptor for electrophotographic photoreceptors.
The present invention was completed based on the discovery that the object can be achieved by using it as an i1 constituent material.

The above object is achieved by providing on a conductive support a photosensitive layer containing at least one amine derivative represented by the following general formula (I) or [11]. In each formula, R~R4 are the same or different, hydrogen atom, halogen atom, Iw substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or represents an unsubstituted aryloxy group or a 1θ-substituted or unsubstituted amino group,
R5~R engineering. represent the same or different water S atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted cyano group, and Ar is a substituted or unsubstituted aromatic group. Carbocyclic (9) Represents a group or a substituted or unsubstituted aromatic carbocyclic group.
(1 Was.) That is, in the present invention, the general formula [E] or (II)
The amine derivative represented by the above is used as a photoconductive substance to form a photoreceptor layer of an electrophotographic photoreceptor, or the amine m conductor? Focusing on its excellent carrier transport ability, it is used as a carrier transport material and combined with a carrier generating material to form a photosensitive layer of a so-called functionally separated photoreceptor in which carrier generation and transport are performed by separate materials. . As a result, the physical properties of the film deteriorate,
In addition, there is little fatigue deterioration even when subjected to repeated use.
An electrophotographic photoreceptor that can exhibit stable characteristics can be provided. (3) Specific examples of the amine derivatives represented by the general formula [E] or (It) that can be effectively used in the present invention include those having the structural formula shown below, but of course, It is not limited.

(lO) ) H3 ) (11) (4) CH3 (18) (10) (12) (13) (14) (14) (15) CH3 (16) (15) (17) CH3 (18) (19 ) (20) CH3 (21) (22) (17) (23) (24) (25) (18) (26) (27) (28) (19) (29) (30) (31) (32) (34) (21) (35) (36) (22) (38) (39) (40) (23) (46) N (25) (47) ρI (26) (51) (27) (56) (57) (29) (58) (30) (60) The above amine derivatives can be easily synthesized by known methods. For example, as shown in the following reaction formula (■) or (■), a 9゜10-dihydroacridine derivative represented by the general formula [1] or an iminobenzyl derivative represented by the general formula [■] and an aromatic halide (X- Indicated by Ar.

) is reacted with copper powder as a catalyst in the presence of an aphrodisiac group? b
By doing so, an amine derivative represented by the general formula [E] or (ID) can be obtained.

(31) Reaction formula ■ [■] Reaction formula ■ [IV] [11) R1 to R engineering. each represents the same thing as shown for the above general formulas [Engine] and [■].

Next, a typical method for synthesizing the amine derivative used in the present invention will be specifically explained.

Synthesis Example 1 (Synthesis of Exemplary Compound (1)) 9.10-dihyFo7ri'Jlysine1. / jil (
0,/%le), benzene iodide 2q,5h(0,12
mol), 15 g of anhydrous carbonated potassium, and II g of copper powder were mixed and reacted at a temperature of 210'C"'C!r hours. The reaction product was extracted by adding 300" of toluene, and the extract was completely concentrated to silica gel. Purification by column chromatography gave colorless crystals.The yield was 21.9 ml (yield 1/%), and the melting point was ~//7°C.

Synthesis Example 2 (Synthesis of Exemplary Compound (14)) Iminobenzyl/9. S (J (0,7 mol), benzene iodide xp
, s 9 (o, t2 mol), anhydrous carbonic acid linium l
Dac and copper powder are mixed and reacted at a temperature of 210 to 220'C for a period of time, and 3 oofn of toluene is added to the reaction product. , for extraction, concentrate the extract, and apply it to a silica gel column (3
3) Purified by chromatography and recrystallized from ethanol to obtain colorless crystals. Yield is 23.92 (yield rr%)
, the melting point is rg~lrg'c.

Synthesis Example 3 (Synthesis of Exemplified Compound (31)) After dropping phosphorus oxychloride j9 into 2.03 moles (0.07 moles) of N-methylformanilide, while keeping the temperature below 70°C, Exemplary compound (14) (7) 3 obtained in Synthesis Example 2
．． ! 29 (0,073%) 'fir was added gradually and reacted for an additional 2 hours at a temperature of <RTI ID=0.0>g,</RTI> followed by boiling water.

- poured. After decanting the supernatant and washing the residue with hot water, it was recrystallized using methanol 3o-.
-dihydro-5-(1)-formylphenyl- 5H-
Dibenzo[b,f]azepine3. ψ2ノ(yield, r7.
9%).

Then diethyl p-methoxybenzylphosphonate2.
5 g + 0.01 mole) was dissolved in N,N-dimethylformamide 20-, and sodium chloride was dissolved under water cooling.
)/． Or 9 (0.02% le) to 7IO! 10.11-dihydro-5-(p-formylphenyl)-5H-dibenzo(b,f)azepine x
, qq 9 (84)N,N-dimethylformamide 20-solution was added dropwise, stirred at room temperature for 3 hours, heated overnight, and then soaked in 20 tons of ice water.
The precipitated crystals were collected by filtration. This was recrystallized twice from P acetonitrile, and the exemplified compound (31
) to 3. Baku (yield 7K.0%) was obtained. Fusion A 13 /
2t~/21'CT exists.

The above-mentioned amine derivatives are almost photosensitized to light in the visible range. Therefore, in order to be able to carry out the photostep with visible light, the sensitization process must be carried out. It is necessary. Various methods have been proposed for sensitizing the Ariiso photoconducting compound, and the first method is a method of spectral sensitization (dye sensitization) by adding an organic dye. A second method is to add a substance that forms a charge transfer meisen, and this substance is an electron-accepting substance since the amine derivative described above in the present invention is an electron-donating substance. It is preferable that there be. In the present invention, when the amine derivative is used as a carrier transport material, other organic dyes or pigments or inorganic photoconductive substances can absorb visible light and generate carriers (85). By combining it with a substance to form a functionally separated photoreceptor, it is also possible to perform a de facto sensitization process.

All of the sensitization methods described above are effective for the amine derivatives used in the present invention, and an appropriate method may be selected from various other conditions.

Typical examples of organic dyes for spectral sensitization used in spectral sensitization are as follows.

(A-1) Triphenylmethane dyes such as methyl violet, crystal violet, and malachite green (A-2) Xanthine dyes such as erythrosine and rose bengal (A-3) Thiazine dyes such as methylene blue and methylene green (A-2) -4) Caprylic blue,
Oxazine dyes such as melt trouble (A-5) Cyanine dyes such as thiacyanine and oxacyanine (A-6)
Styryl dyes such as p-dimethylaminostyrylquinoline TA-7) Bylylium ring dyes such as pyrylium salts, thiapyrylium salts, benzopyrylium salts, and benzothiapyrylium salts (71-8) 3,3'-dicarbazoli Preferred electron acceptors for lumethane color patches include:
2,4.7-Dolinitrofluorenone, jq, 4,5.
Lewis acids such as 7-titranitrofluorenone, chloranil, and tetracyanoquinodimethane may be mentioned.

Furthermore, as carrier-generating substances to be used when constructing a functionally separated photoreceptor, all of the various dyes mentioned above as organic dyes for spectral sensitization can be effectively used, but in addition, the following can be used. be.

(B-1) Azo dyes such as monoazo dyes, bisazo dyes, and trisazo dyes (B-2) Perylene dyes such as herilenic anhydride and perylenic acid imide (B-31 Indigoid dyes such as indigo and thioindigo (B-31) -'4) Polycyclic quinones such as anthraquinone, bi-1/quinone, and flavanthrones (B-5) Quinacridone dyes (B-6) Bisbenzimidazole dyes (37) (B-7) Indanthrone dyes Pigments (B-8) Square lium pigments (B-9) Phthalocyanine pigments such as gold @ phthalocyanine and metal-free phthalocyanine (B-10) Selenium and selenium alloys (B-11) Inorganic pigments such as cadmium sulfide and cadmium selenide Photoconductor (B-12) In addition to the eutectic complex formed from pyrylium salt dye, thiapyrylium salt dye and polycarbonate, a method using a chemical sensitizer can also be effectively used.

Since the amine derivative used in the present invention does not have the ability to form a film by itself, the photosensitive layer is constructed by combining various binders.

As the binder used here, any binder can be used, but a hydrophobic, high IT rate, electrically insulating film-forming polymer may be used. It is preferable to use Examples of such high molecular weight polymers include the following (38), but are not limited thereto.

(0-11 Polycarbonate (0-2) Polyester (0-3) Methacrylic resin (C-4) Acrylic resin (C-5) Polyvinyl chloride (0-6) Polyvinylidene chloride (0-7) Polystyrene (0- a) Polyvinyl acetate (0-91 styrene-butadiene copolymer (0-10)
Vinylidene chloride-acrylonitrile copolymer (C-111 Vinyl m-vinyl acetate copolymer (C-1)
2) Cyclized vinyl-vinyl acetate-maleic anhydride resistant/common combination (C-13) Silicone resin (0-14) Silicone-alkyd resin (0-151 Phenol-formaldehyde resin (C-16) Styrene-alkyd resin (0-17) ) Poly-N-vinyl Rubazole (89) These binders can be used alone or in a mixture of two or more.

To explain the mechanical structure of the electrophotographic photoreceptor of the present invention, in one example of the present invention, as shown in FIGS. layer 2, and a carrier transport layer 3 containing the above-mentioned amine derivative as a main component of the carrier transport substance.
A photosensitive layer consisting of a laminate of As shown in FIGS. 3 and 3, this photosensitive Mu may be provided through an intermediate layer j provided on a conductive support l. As described above, when the 2N structure is used after exposure to light, an electrophotographic photoreceptor having the best electrophotographic properties can be obtained.

Further, in the present invention, as shown in FIGS. 5 and 6,
A photosensitive layer μ″, which is formed by dispersing a carrier-generating substance 7 in the form of fine particles in a carrier-transporting layer containing the carrier-transporting substance as a main component, is deposited directly on the conductive support l or with an intermediate N
It may also be provided via a cable.

Furthermore, without using a carrier-generating substance, the amine derivative can be treated with a sensitizing dye or Lewis I! ! ! 2nd class PIII is obtained.

Here, when the photosensitive layer tIt has a two-layer structure, whether the carrier generation layer 2 and the carrier transport layer 3 should be the entire upper layer depends on whether the charging polarity is selected as positive or negative. That is, when forming a negatively charged photosensitive layer, it is advantageous to use the carrier transport layer 3 as an upper layer, since the amine derivative in the carrier transport layer 3 is a substance having a high transport ability for holes. Because there is.

Further, the carrier generation layer 2 comprising the photosensitive layer Hirona having a two-layer structure is
It can be formed directly on the conductive support 1 or the carrier transport layer 3, or after providing an intermediate layer such as an adhesive layer or a barrier layer if necessary, by the following method.

(1) Vacuum evaporation method (2) Method of applying a solution of carrier-generating substance dissolved in an appropriate solvent (3) Forming the carrier-generating substance into fine particles in a dispersion medium using a ball mill, homomixer, etc. ) The thickness of the carrier generation layer 2 formed in this way is o
, oi to 5 mils and 5 microns, and more preferably 00OS to 3 microns.

Further, the thickness of the carrier transport layer 3 can be changed as necessary, but it is usually preferably 5 to 30 microns. The composition ratio in this carrier transport layer 3 is preferably such that the binder is in an amount of 0 g to 0 parts by weight per 1 part by weight of the carrier transport material whose main component is the amine derivative described above. When forming a photosensitive layer in which a substance is dispersed, binder and
It is preferable to use S within a range of parts by weight. Further, when the carrier generation layer 2 is configured as a dispersed layer using a binder, it is preferable to use the binder in an amount of 5 parts by weight or less per 1 part by weight of the carrier generating substance.

The conductive support l used in the construction of the electrophotographic photoreceptor of the present invention may be a gold plate, for example, a conductive polymer, a conductive compound such as indium oxide, or, for example, aluminum, palladium, or gold. Paper, plastic film, etc. that have been made conductive by coating, vapor depositing, or laminating a thin layer of gold tint, etc., are used. The intermediate layer S such as the adhesive layer or barrier layer may be made of organic polymers such as gelatin, casein, starch, polyvinyl alcohol, vinyl acetate, ethyl cellulose, carboxymethyl cellulose, etc., in addition to the polymer used as the binder. Alternatively, fermented aluminum may be used.

The electrophotographic photoreceptor of the present invention has the above-described structure, and as is clear from the examples described later, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and is particularly suitable for use in repetitive transfer electrophotography systems. It has excellent durability with little fatigue deterioration even when

Examples of the present invention below? Although a specific explanation will be given, the actual ms of the present invention is not limited thereby.

(43) Example 1 Selenium was vapor-deposited on a conductive support formed by vapor-evaporating aluminum onto a polyester film to form a carrier generation layer with a thickness of 0.05 microns. Next, the exemplified compound (2
) total weight part and polycarbonate [Panlite L-1
250J (manufactured by Yodai Kasei Co., Ltd.)
A carrier transport layer was formed by dissolving this solution in a dichloroethane qO layer and applying the solution so that the film thickness after drying was 1/micron, thereby producing an electrophotographic photoreceptor of the present invention.

This electrophotographic photoreceptor was tested using an electrostatic paper tester "5".
The electrophotographic characteristics were measured using a dynamic method using a model P-428 (manufactured by Isao Kawaguchi City Machinery Works).

That is, the surface of the photosensitive layer of the photoreceptor is charged with a voltage of −,4;, OK.
The surface potential VA when the photoreceptor is charged for 5 seconds with
The exposure amount required to attenuate the irradiated FT surface charge (ff, VA by half) to 51uX (half-reduced exposure amount) E
1 (lux-sec) and the surface if+i potential (residual potential) after exposure with an exposure amount of 30 lux-sea ■8
Similar measurements were repeated 100 times for each.

The results are as shown in Table 1.

Table 1 Comparative Example 1 A comparative example was prepared in the same manner as in Example 1 except that N-)lylcarbazole represented by the formula (451) was used instead of Exemplified Compound (2) as carrier transport All electrophotographic photoreceptors were prepared and the same measurements were conducted.The results are shown in Table 2.

As is clear from the above results, the electrophotographic photoreceptor of the present invention according to Example 1 has better sensitivity, residual potential characteristics, and stability during repeated use than the comparative electrophotographic photoreceptor according to Comparative Example 1. It is extremely superior in terms of performance.

Example 2 A 0.0-thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer [Eslec MF-10J (manufactured by Tansui Kagaku Co., Ltd.)] was placed on a conductive support made of a polyester film laminated with aluminum foil. ! ; Miku (46) Ron's middle layer +eke, on top of that, dibromoanthanthrone [Monolite Red 2Y J (C, 1, lG5
980 (l 1.O, 1, manufactured by Co., Ltd.) was evaporated to a thickness of 0, s.
A carrier generation layer of Miku-an was formed. Then, 90 parts by weight of 1,2-dichloroethane was added to 10 parts by weight of Exemplified Compound 9 (20) and polycarbohydrate (Panlite L-1250J (manufactured by Hitsuji Kasei Co., Ltd.)). The solution was dissolved and applied to a dry film thickness of 11 microns to form the entire carrier transport layer, thereby producing an electrophotographic photoreceptor of the present invention.

The same measurements as in Example 1 were performed on this electrophotographic photoreceptor. The results are shown in Table 1@3.

Table 3 (47) Comparative Example 2 A comparative electrophotograph was taken in the same manner as in Example 2, except that N-anisylcarbazole represented by the structure formula was used as a carrier transport substance in place of exemplified compound (2o). A photoreceptor was prepared and the same measurements were performed. The results are shown in Table 4.

Compared to the comparative electrophotographic photoreceptor according to Comparative Example 2, the N1 photoreceptor of the present invention is significantly inferior in sensitivity, residual potential characteristics, and stability during repeated use.

Examples 3-6 Exemplary compounds (3) and (6) as carrier transport substances.

Example 2 except that (25) and (30) were used, respectively.
A total of q types of electrophotographic photoreceptors of the present invention were prepared in the same manner as in Example 1, and the initial characteristics of each of them were measured in the same manner as in Example 1. The results are shown in Table 5.

Table 5 (49) As is clear from the above results, all of the electrophotographic photoreceptors of the present invention (jS) have high sensitivity, residual potential, and extremely excellent performance.

Example 7 On the conductive support provided with the intermediate layer used in Example 2, 1 part by weight of the bisazo pigment represented by the structural formula was added, and 2 parts of ethylenediamine, h-butylamine, and tetrahydrofuran were added.
: /, 0 : Mixed solvent mixed at a ratio of 2.2 /
A carrier generation layer was formed by dissolving the obtained solution in 110 parts by weight and applying the resulting solution to a film thickness of 0.3 microns after drying. "Acribet" (Mitsubishi Rayon Co., Ltd.!!J)
70 parts by weight and p1.2-dichloroethane (50) Coating solution dissolved in Nqo place sound 15 Film 19 after completely drying
A carrier transport layer was formed by producing a carrier transport layer such that the particle diameter was 15 microns, thereby producing an electrophotographic photoreceptor of the present invention.

The initial chewiness of this electrophotographic photoreceptor was tested with one oil in the same manner as in Example 1. The results are shown in Table 6.

Table 6 This electrophotographic photoreceptor is also used for electrophotographic copying FiWrU-B.
When we conducted a copying test using the iX 2000RJ (manufactured by Konishi Rokusha Teikosha), we were able to obtain a copy that was faithful to the original, had high contrast, excellent gradation and resolution, and after 2000 copies were made. Even when the copy I [! ]I image was obtained.

(51) Comparative Example 8 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 7, except that a compound represented by the following physical property formula was used as a carrier transport material, and the same measurements were performed. The results are shown in Table 7.

Table 7 Also, when this electrophotographic photoreceptor for comparison was attached to an electrophotographic photoreceptor [U-Bix 2000RJ (manufactured by Konishiroku Photo Industries Co., Ltd.) in the same manner as in Example 7, and a copying test was conducted, it was found that at the initial stage, the image did not match the original image. Faithful and contrast, since I did it 200 times I! The vomiting of iIl replacement fa l& and the increase in capri become more frequent.1. When the number of times exceeded tOO, the contrast was lost and only a very unclear copy image was obtained.

As is clear from the above results, the electrophotographic photoreceptor of the present invention is significantly superior in durability, particularly when repeatedly used, compared to the comparative electrophotographic photoreceptor.

Example 8 Polyester [Vylon 200J
(Toyobo IJA) with a thickness of 0.7 microns, a-(p-dimethylaminophenyl) -
One part of 2,6-diphenylthiovirylium verchlorate was dissolved in 30 parts by weight of dichloromethane, and then 10 parts by weight of polycarbonate "Nipiron S-1000J (manufactured by Sanshi Gas Kagaku Co., Ltd.) and exemplified compounds were added. A coating solution obtained by dissolving 6 parts by weight of (53) with TJO and stirring thoroughly is applied onto the intermediate layer (53) to a dry film thickness of 72 microns to form a photosensitive layer. Thus, an electrophotographic photoreceptor of the present invention was prepared.

Measurements were performed on this electrophotographic photoreceptor in the same manner as in Example 1. The results are shown in Table 8.

Table 8 This electrophotographic photoreceptor is also used as an electrophotographic premise 1'-U-Bi.
When I carried out a copying test using the X 2000RJ (manufactured by Konishiroku Photo Industry Co., Ltd.), I was able to obtain a copy that was faithful to the original image, had high contrast, and had excellent sharpness and resolution, with a film thickness of I 500. Even when the printing was carried out, a good copy image was obtained as in the initial stage.

Furthermore, the characteristics of the electrophotographic photoreceptor after 5ooo rotations (54
) sex was measured. The results are shown in Table 9.

As is clear from the results in Table 9 and above, the electrophotographic photoreceptor of the present invention is extremely excellent in sensitivity, residual potential characteristics, and durability.

Example 9 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 7 except that a bisazo pigment represented by the following structural formula was used as a carrier generating substance.

(55) n Measurements were performed on this electrophotographic photoreceptor in the same manner as in Example 1. The results are shown in Table 1O.

Table 1o This electrophotographic photoreceptor was also used in an electrophotographic copying machine "U-BiX".
2000RJ (manufactured by Konishiroku Photography Co., Ltd.) and conducted a copying test to check its durability.
Durability of more than 10 times was obtained.

A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 9, except that a compound represented by the Shimoki formula was used as a carrier transporting substance, and all measurements were carried out in the same manner as in Example 1. The results are shown in Table 11.

Remaining 11 Tables In addition, this electrophotographic photoreceptor for comparison was installed in an electrophotographic copying machine I'U-BiX 2000RJ (manufactured by Konishi Roku Photo Industry Co., Ltd.) in the same manner as in Example 9, and a copying test was conducted, resulting in 300 copies. The fog has increased since I did it.
The durability was extremely inferior to that of the electrophotographic photoreceptor of Example 9 (57), and it could hardly be put to practical use.

Example 10 A layer of vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-LEC MF-10J (manufactured by Kansui Kagaku Co., Ltd.) with a thickness of O and OS was placed on a conductive support made of a polyester film laminated with aluminum foil. A micron intermediate layer is provided, and on top of that, dibromoanthanthrone ``Monolite Red 2YJ (0,I.

2 parts by weight of A 59800 (manufactured by I, O, 1, Inc.) and 1 part by weight of polycarbonate [Panlite L-1250J (manufactured by Yondaika 6 & Co., Ltd.) and 1,2-dichloroethane>tao
The film after drying the coating liquid obtained by dispersing it in the heavy fit area ~
A carrier generation layer was formed by applying the coating to a thickness of 1 micron. Next, 5 parts by weight of Exemplified Compound (42), 1 part by weight of Exemplified Compound (57), and 10 parts by weight of polycarbonate "Panlite L-1250J (manufactured by Yondai Kasei Co., Ltd.) were added to 90 parts by weight of 1,2-dichloroethane. A carrier transport layer was formed by dissolving this solution and applying the solution to a dry film thickness of 12 microns, (58) thereby producing an electrophotographic photoreceptor of the present invention.

The same measurements as in Example 1 were performed on this electrophotographic photoreceptor. The results are shown in Table 12.

Table 12 This again? [The secondary photographic photoreceptor is installed in an electrophotographic copying machine - BiX
Attached to 2000RJ (manufactured by Konishiroku Photo Industry Co., Ltd.),
oo.

After carrying out the copying test twice, similar measurements were carried out again. The results are shown in Table 18.

Table 18 (59) As is clear from the above results, the electrophotographic photoreceptor of the present invention has poor charging characteristics, #, degree, residual potential characteristics, and image forming characteristics, and even after repeated use, these characteristics do not improve. The change is small and the durability is poor.

[Brief explanation of the drawing]

FIG. 1 to FIG. l... Conductive support 2... Carrier generation layer 3
,...Carrier transport layer t...Photosensitive layer j...Intermediate layer t...Carrier transport layer 7...Carrier generating substance Figure 1 Nest Figure 2 Figure 3 Procedural amendment (voluntary) 1982 Haruki Shimada, Commissioner of the Japan Patent Office (March 31, 2013) 1. Indication of the case 1982 Patent Application No. 182320 2. Title of the invention: Electrophotographic photoreceptor 3. Relationship with the person making the amendment case 4. Place of filing of the patent: Tokyo 1-26-2-4 Nishi-Shinjuku, Shinjuku-ku, Tokyo;
Agent name (7875) Patent attorney Masahiko Oi 5
, Date of amendment order6, Number of inventions increased by amendment7, Subject of amendment (1) Claims column in the specification (2) Detailed explanation of the invention column in the specification (2) (1 ) As stated elsewhere (2) ]) "Replaced or unsubstituted" is deleted from the second line from the bottom of page 8 of the specification. 2) In the fifth line from the bottom of page 30, "iminobenzyl" is corrected to "iminodipencil." 3) On page 31 of the same page, correct "Reaction formula ■ [1] Ar N)" as follows0 Reaction formula ■ Tomi [1] R, R. 4) On page 32, line 5 from the bottom, “iminobenzyl J”
Iminodibenzyl,” he corrected. (1) Attachment 2, Claims]) An electrically conductive support and a sensor provided on the electrically conductive support.
An electrophotographic photoreceptor comprising a layer (layer), wherein the first photosensitive layer contains at least one type of gold, an amine derivative C2 represented by the following general formula [1] or [Il]. General formula [1] Ar General formula [11 (2) (In the 4-layer 1 formula, R1-R4 are the same or different from each other,
Hydrogen atom, halogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy group, substituted or unsubstituted 7-aryl group, substituted or (7 unsubstituted aryloxy group or II′i represents a substituted or unsubstituted amino group; 1, R, to RIo are each the same or different, hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted represents an aryl group or a cyano group,
Ar represents a substituted or unsubstituted aromatic carbocyclic group or a substituted or unsubstituted aromatic heterocyclic group. 2) The electrophotographic image forming apparatus according to claim 1, wherein the layer containing the amine derivative constitutes a carrier transport layer, and the photosensitive layer is constituted by a laminate of the carrier transport layer and the carrier generation layer. p-bound light body. 3) The electrophotographic photoreceptor according to claim 1, item 1(3), wherein the layer containing the amine derivative contains a carrier-generating substance, and this layer constitutes the photosensitive layer.

Claims (1)

[Scope of Claims] 1) Comprising an electrically conductive support and a photosensitive layer provided on the electrically conductive support, the photosensitive layer having the following general formula CI) or [■
An electrophotographic photoreceptor containing at least one amine conductor represented by the following. General formula [Eng. ¥-substituted alkoxy group, oxy-substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted amino group; R5 to R are the same or different hydrogen atoms; , halogen atom, fl, fl * L, < represents an unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted cyano group, lr is a substituted or unsubstituted aromatic group with !i; 2) The layer containing the amine V4 conductor constitutes a carrier transport layer, and the photosensitive layer is a carrier transport layer and a carrier transport layer. The electric current according to claim 1, which is constituted by a laminate including a generating layer. Child manuscript photoreceptor. 3) The electrophotographic photoreceptor according to claim 1, wherein the layer containing the amine conductor contains a carrier-generating substance, and this layer constitutes the photosensitive layer (8).