GB2350690A

GB2350690A - Electrophotographic photosensitive body and method of manufacture

Info

Publication number: GB2350690A
Application number: GB0001431A
Authority: GB
Inventors: Yoichi Nakamura; Teruo Sasaki; Kenichi Hara; Hideki Kina; Shinjirou Suzuki
Original assignee: Fuji Electric Imaging Device Co Ltd
Current assignee: Fuji Electric Imaging Device Co Ltd
Priority date: 1999-01-29
Filing date: 2000-01-22
Publication date: 2000-12-06
Anticipated expiration: 2020-01-22
Also published as: GB2350690B; GB0001431D0; DE10002834A1

Abstract

An electrophotographic photosensitive body comprises a photosensitive layer formed on a conductive substrate. The photosensitive layer comprises a phthalocyanine compound and a phthalocyanine compound as a photoconductive material. The content of the phthalocyanine dimer compound in the layer that contains the phthalocyanine compound is no less than 100 nmol and no more than 300 mmol per 1 mol of the phthalocyanine compound. The electrophotographic photosensitive body has excellent electrophotographic characteristics, particularly superior potential retention.

Description

2350690 ElectrophotogrUhic Photosensitive Body and Method of Manufacturing

Same The present invention relates to an electrophotographic photosensitive body (hereafter simply referred to as a "photosensitive body"), and, more particularly to an electrophotographic photosensitive body for use in a printer, a copier, or facsimile terminal equipment based on an electrophotographic method, the photosensitive body having excellent retention due to an improved photoconductive material in a photosensitive layer provided on a conductive substrate and containing an organic material. The present invention also re4ates to a method for manufacturing the above electrophotographic: photosensitive body.

Electrophotographic photosensitive bodies are required to provide a function for retaining surface charges in a dark environment, a function for receiving light to generate charges, and a function for also receiving light to transport charges. These photosensitive bodies include single-layer photosensitive bodies that provide all these functions in a single layer and laminated photosensitive bodies wherein these functions are separated into corresponding layers. In the later case, the photosensitive bodies comprise a layer that principally contributes to charge generation and a layer that principally contributes to retention of surface charges in a dark environment and charge transportation after light reception.

For example, the Carlson method is applied to image formation based on electrophotography using electrophotographic photosensitive bodies. With this method, images are formed by charging a photosensitive body in a dark environment by means of corona discharge; forming an electrostatic latent image of characters or a picture from a manuscript on a surface of the photosensitive body which is already charged; developing the formed electrostatic latent image using a toner; and transferring the developed toner image to a support such as paper for settlement. After transfer of the toner image, the photosensitive body is reused after static elimination, removal of residual toner, and optical static elimination.

The conventional electrophotographic photosensitive body comprises an inorganic photoconductive substance, such as selenium, a selenium alloy, zinc oxide, or cadmium sulfide, which is dispersed in a resin binding 2 agent; or an organic photoconductive substance such as poly-Nvinylcarbazole, polyvinylanthracene, a phthalocyanine compound, or a bisazo compound, which is dispersed in a resin binding agent or vacuumdeposited thereon.

On the other hand, of these organic photoconductive substances, various studies have been conducted on the purification of Phthalocyanine compounds. Particularly, a /i-oxo dimer of phthalocyanine and a g dimer thereof, which have an element capable of assuming an oxidized state with an oxidation number of +3 or more (hereafter referred to as "multioxidized-element-included phthalocyanine"), are well known and described in PHTH ALOCYANINES, C.C. Leznoff et al, 1989 (VCH Publishers. Inc.).

As described above, the use of the multioxidized-element-included phthalocyanine compound as a photosensitive material for electrophotographic photosensitive bodies is well known, and various attempts have been made to purify this compound. Of the impurities contained in the multioxidized-element-included phthalocyanine compound, however, those substances that relate to the characteristics of electrophotographic photosensitive bodies have not been definitely identified. That is, despite various purification methods for the multioxidized-element-included phthalocyanine compound and various examinations of polymers of phthalocyanine compounds, the relationship between impurities resulting from the synthesis of the multioxidizedelement-included phthalocyanine compound and electrophotographic characteristics, and in particular, potential retention, has not been clarified.

It is thus an object of the present invention to clarify this relationship to provide an electrophotographic photosensitive body having excellent electrophotographic characteristics, and in particular, superior potential retention, as well as a manufacture method therefor that, using a coating liquid, can form a photosensitive layer having superior potential retention.

In the course of enthusiastic examinations for attaining the above object, the inventors added a phthalocyanine dimer compound as well as phthalocyanine to a photosensitive layer on a conductive substrate within a 3 specific ratio to the phthalocyanine's content as a photoconductive material to find a substantial increase in the potential retention of the photosensitive body. Consequently, the inventors have completed an electrophotographic photosensitive body according to the present invention.

That is, the present invention provides an electrophotographic photosensitive body having a photosensitive layer formed on a conductive substrate, the photosensitive layer containing a phthalocyanine compound as a photoconductive material, characterized in that:

the content of the phthalocyanine dimer compound in a layer having the phthalocyanine compound is 100 nmol or more and 300 nmol or less per 1 mol of the phthalocyanine compound.

In addition, in manufacturing the electrophotographic photosensitive body, the inventors added a phthalocyanine compound and a phthalocyanine dirner compound to a coating liquid containing a charge generation material in such a way that the content of the phthalocyanine dimer compound was within a specific ratio to the content of the phthalocyanine compound. This was done in order to find a substantial increase in the potential retention of the photosensitive body. Consequently, the inventors have completed a method according to the present invention.

That is, the present invention provides a method for manufacturing an electrophotographic photosensitive body, having the step of forming a photosensitive layer by coating, onto a conductive substrate, a coating liquid containing a charge generation material, characterized in that:

the coating liquid contains a phthalocyanine compound and a phthalocyanine dimer compound; and the content of the phthalocyanine dimer compound is 100 nmol or more and 300 mmol or less per 1 mol of the phthalocyanine compound.

The "dimer" herein refers to include "multimers" having a dimer with one or more phthalocyanines bound thereto.

The photosensitive layer of the electrophotographic photosensitive body according to the present invention includes both the single-layer and laminated types and is not limited to either type. In addition, the coating liquid in the manufacture method according to the present invention is applicable to various coating methods such as dip and spray coating methods and is not limited to a particular method.

4 A specific construction of the photosensitive body according to the present invention will be described below with reference to drawings, in which:

Figure 1 is a typical sectional view of a negative-charged laminated electrophotographic photoconductive body that is an example of the present invention; and Figure 2 is a spectrum diagram showing an example of a MALDI-TOF-MS spectrum of (A-oxo)bis(phtalocyaninato titanium) compound-containing titanyloxophthalocyanine according to the present invention.

Electrophotographic photosensitive bodies include negative-charged laminated photosensitive bodies, positive-charged laminated photosensitive bodies, and positive-charged single-layer photosensitive bodies. While the present invention will be specifically described below taking a negative-charged laminated photosensitive body by way of example, preferable components and methods for the formation or manufacture of the photosensitive body other than the phthalocyanine compound according to the present invention may be selected as appropriate.

As shown in Figure 1, the negative-charged laminated photosensitive body is formed of a conductive substrate 1, an undercoat layer 2 laminated thereon, and a photosensitive layer 5 further laminated thereon. Because the photosensitive layer 5 comprises a charge generation layer 3 and a charge transportation layer 4 laminated thereon, it is of a function separation type, with its functions separated into the charge generation layer 3 and the charge transportation layer 4. Incidentally, both of the above-mentioned types may omit the undercoat layer 2.

The conductive substrate 1 serves as both electrodes of the photosensitive body and a support for each of the other layers, and may be shaped like a cylinder, a plate, or a film. Its material may be metal, such as aluminium, stainless steel, nickel, or an alloy thereof, or glass or resin subjected to conduction processing.

The undercoat layer 2 may comprise alcohol-soluble polyamide, solutionsoluble aromatic polyamide, or thermosetting urethane resin. The alcoholsoluble polyamide is preferably a copolymerized compound such as nylon 6, nylon 8, nylon 12, nylon 66, nylon 610, or nylon 612, or N-alkyl-modified or N-alkoxyakl-modified nylon. Specific examples of these compounds include AMILAN CM8000 (manufactured by Toray Industries, Inc.; 6/66/610/12 copolymerized nylon), ELBAMIDE 9061 (manufactured by Du Pont Japan Co. Ltd.; 6/66/612 copolymerized nylon), DIAMIDE T-170 (manufactured by Daisel-Husels Co., Ltd.; copolymerized nylon chiefly containing nylon 12). Furthermore, the undercoat layer 2 may contain inorganic fine powders such as titanium oxide (T'02), Sn02, alumina, calcium carbonate, or silica.

The charge generation layer 3 is formed by vacuum-depositing an organic photoconductive substance on the undercoat layer or coating the undercoat layer with a material comprising particles of the organic photoconductive substance dispersed in a resin binding agent, and receives light to generate charges. The charge generation layer 3 must have a high charge generation efficiency and be able to inject generated charges into the charge transportation layer 4. Preferably, the charge generation layer 3 is less dependent on electric fields so as to appropriately inject charges into the charge transportation layer despite low electric fields.

The charge generation substance must contain at least a phthalocyaninebompound, but may be used with another charge generation substance, for example, pigments or dyes such as various azo, quinone, indigo, cyanine, squarilium, or azulenium compounds.

According to the present invention, the content of phthalocyanine dimer compound in the charge generation layer 3 is 100 nmol or more and 300 mmol or less, preferably 200 nmol or more and 200 mmol or less, per 1 mol of phthalocyanine compound. By adding a particular amount of phthalocyanine dimer compound to the phthalocyanine compound, the potential retention increases substantially. This mechanism is not totally clear, but the following assumption is possible: when the content of phthalocyanine dimer compound is less than 100 nmol, the phthalocyanine compound may be excessively pure, causing crystals to grow excessively or preventing dispersion, and thereby reducing retention. On the other hand, above 300 mmol, the crystal sequence of the phthalocyanine compound may be excessively randomized or the phthalocyanine dimer compound itself may contribute to reducing the retention. The phthalocyanine dimer compound contained in the phthalocyanine compound is not limited to one having the 6 same central element as the phthalocyanine compound, but similar effects can be obtained by using a dimer having a different element.

A method for synthesizing the phthalocyanine compound for use in the present invention is well known, and synthesis can be carried out pursuant to the approach disclosed, for example, in PHTHALOCYANINES C. C. Leznoff et al., 1989 (VCH Publishers. Inc.) or THE PHTHALOCYANINES F. H. Moser. et al., 1983 (CRC Press).

The phthalocyanine compound forming the phthalocyanine dimer compound is preferably titanyloxophthalocyanine. In addition, according to the present invention, it is possible to use a phthalocyanine compound whose central element is selected from a group of transition metals, particularly titanium, vana dium, chromium, manganese, iron, cobalt, nickel, zirconium, niobium, molybdenum, rhodium, cerium, neodymium, samarium, europium, or tungsten. It is also possible to use a phthalocyanine whose central element is selected from a group comprising indium, gallium, aluminium, germanium, tin, antimony, lead, bismuth, silicon, and phosphorous. Furthermore, it is possible to use a phthalocyanine compound into which various functional groups are introduced, such as one represented by the following formula:

R'S R 2 7 0 RE, R 8 k' R15 10 14 11 where M denotes a diatomic element in the Ia family, or an element that can assume an oxidized state of +2 or more, or an oxide, hydroxide, halide, or alcohol salt of said element; and R1 to R16 each denote a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an ester group, an alkyl group, an alkenyl group, an alkoxyl group, an allyl group, or an allyloxyl group and may be the same or different from one 7 another. The present invention also preferably uses non-metal phthalocyanine as the phthalocyanine compound.

The dimer compound of the phthalocyanine compound assumes various forms, for example, a g-oxo metallic phthalocyanine dirner, a A-metallic phthalocyanine dimer, and a g-metallic phthalocyanine oligomer. Preferably, the phthalocyanine dimer compound is a g-oxo dimer compound and more preferably has a Pc-M-0-M-P structure (where Pc denotes a phthalocyanine compound, M denotes an element with an oxidation number of +3 or more, and 0 denotes oxygen). Likewise, the phthalocyanine dimer compound is preferably a A-dirner compound and more preferably has a Pc-MPc structure (where Pc and M are the same as described above).

The phthalocyanine compound and phthalocyanine dimer compound may be detected by matrix assisted laser desorption/ionization time of flight mass spectrometry (hereafter referred to as the "MALDI-TOF-MS method" or simply the "TOF-MS method"), field emission mass spectrometry, high-speed atom-collision mass spectrometry, or electron-impact-ionization mass spectrometry.

Since the phthalocyanine compound and the phthalocyanine dimer compound have a high absorptivity, the MALDI-TOF-MS method enables the phthalocyanine compound to be detected without the addition of a matrix compound. This is true regardless of whether the compound comprises fine powders of grain size less than 400 nm; comprises fine powders of grain size less than 400 nm that are dispersed or dissolved in an organic solvent and then dried and hardened using an appropriate method; or comprises fine powders of grain size less than 400 nm and various resin binding agents which are dispersed or dissolved in an organic solvent and then dried and hardened using an appropriate method. This method can also provide mass spectra reflecting the abundance ratio of the phthalocyanine compound.

If the phthalocyanine compound is titanyloxophthalocyanine and if a roughly synthesized material is subjected to the TOF-MS method, peaks may occur not only for titanyloxophthalocyanine ions having a mass number of 576 but also at a mass number of 1136. Figure 2 shows an example of such a spectrum diagram. Table 1, which is shown below, lists the detected intensity of each component. For isotopic peaks, only maximum peaks are shown.

8 Table 1

Mass number Area intensity ratio 39 0.49 192 0.21 576 100 704 0.80 1136 0.86 Describes peaks of integrated intensity ratio 0.20% or more Calculated assuming that the peak at M = 576 is 100%.

The peak at the mass number of 1136 has the same mass number as the (goxo)bis(phtalocyaninato titanium), so the presence of the (iioxo)bis(phtalocyaninato titanium) compound is obvious if a peak is detected at the mass number of 1136.

When the (g-oxo)bis(phtalocyaninato titanium) compound-containing titanyloxophthalocyanine was examined using a MALDI-TOF-MS analyser (Shimazu Corp., Kornpact MALDI IV), 200 gmol or more of (goxo)bis(phtalocyaninato titanium) per 1 mol of titanyloxophthalocyanine could be detected by optimising the intensity of the irradiated laser beams. In addition, when the abundance ratio of the (goxo)bis(phtalocyaninato titanium) exceeded 300 mmol per 1 mol of titanyloxophthalocyanine, the peak integrated intensity at the mass number of 1136 was ascertained to be more than 30% of that at the mass number of 576.

These components can be removed using the sublimation method. According to this invention, phthalocyanine dimer compounds generated as by- products during synthesis can be used directly.

Since the charge transportation layer is lan-finated on the charge generation layer, the thickness of the charge generation layer is determined by the absorptivity of its charge generating substance and is generally 5 gm or less, and preferably 1 gm or less.

9 The charge generation layer 3 is principally comprised of a charge generation substance to which a charge transportation substance can be added. A resin binding agent for the charge generation layer may be an appropriate combination of polymers or copolymers of polycarbonate, polyester, polyamide, polyurethane, epoxy, polyvinylbutyral, phenoxy, silicone, and ester methacrylate, their halides, and cyanoethyl compounds. In this case, 10 to 5,000 ptslwt, preferably 50 to 1,000 pts/wt, of charge generation substance is preferably used per 100 ptslwt of the resin binding agent.

The charge transportation layer 4 is a paint film consisting of a material that comprises a resin binding agent with a dispersed charge transportation substance, for example, one of or a combination of various hydrazone-based compounds, styryl-based compounds, amine-based compounds, and their derivatives. The charge transportation layer 4 also has a function for retaining the charges of the photosensitive body in a dark environment as an insulating layer while transporting charges injected from the charge generation layer during light reception. The resin binding agent for the charge transportation layer may be a polymer or a copolymer of polycarbonate, polyester, polystyrene, or ester methacrylate, and its important characteristics are its mechanical, chemical, and electric stability, adhesion, and compatibility with the charge transportation substance. In this case, 20 to 500 ptslwt, and preferably 30 to 300 pts/wt of charge transportation substance, is used per 100 pts/wt of the resin binding agent. The thickness of the charge transportation layer is preferably between 3 and 50 gm and more preferably between 15 and 40 gm so as to maintain an effective surface potential.

Although specific examples of the present invention will be shown below, the present invention is not limited to these examples.

Example 1 Formation of the Undercoat Layer An undercoat layer coating liquid was produced by mixing together 70 ptslwt of polyamide resin (manufactured by Toray Industries Inc.; Amilan CM8000) and 930 pts/wt of methanol (manufactured by Wako Pure Chemical Industries Co., Ltd.). The dip coating method was used to coat this undercoat layer coating liquid on an aluminium. substrate in order to form an undercoat layer having a thickness of 0.5 tm after drying. Formation of the Charge Generation Layer Eight hundred grams of o-phthalodinitryl (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.8 L of quinoline (manufactured by Kanto Chemical Co., Ltd.) were added in a reaction vessel and agitated. In a nitrogen atmosphere, 297 g of titanium tetra-chloride (manufactured by Kishida Chemical Industries Co., Ltd.) were added to the mixture by droplets, and the mixture was then agitated. After adding the droplets, the mixture was heated at 180'C for 15 hours and then further agitated.

This reaction solution was cooled down to 130'C, subsequently filtered, and then washed in 3-L of N-methyl-2-pyrrolidinone (manufactured by Kanto Chemical Co., Ltd.). In a nitrogen atmosphere, this wet cake was heated and agitated in 1.8 L of N-methyl-2-pyrrolidinone at 160'C for 1 hour. The cake was cooled, filtered, and sequentially washed in 3 L of N-methyl2-pyrrolidinone, 2 L of acetone (manufactured by Kanto Chemical Co., Ltd. ),2 L of methanol (manufactured by Kanto Chemical Industry), and 4 L of hot water.

The titanyloxophthalocyanine wet cake obtained in the above manner was further heated and agitated in a dilute hydrochloric acid, which is a mixture of 4 L of water and 360 mL of 36% hydrochloric acid, (manufactured by Kanto Chemical Industry Co., Ltd.) at 80'C for 1 hour. The cake was cooled, filtered, and washed in 4 L of hot water, followed by drying. It was subsequently purified three times by means of the vacuum sublimation method and then dried.

Then, 200 g of this dried product was added to 4 kg of 96% sulphuric acid (manufactured by Kanto Chemical Co., Ltd.) at -50C. This mixture was simultaneously cooled and agitated so that the temperature would not exceed -5'C. The mixture was then cooled for 1 hour, while being kept at 5'C, and then agitated. Furthermore, this sulphuric. solution was added to 35 L of water and 5 kg of ice, while being simultaneously cooled and agitated so that the temperature would not exceed 10'C. The solution was then cooled for 1 hour and agitated, then filtered and washed in 10 L of hot water.

11 The solution was further heated and agitated in a dilute hydrochloric acid, which is a mixture of 10 L of water and 770 mL of 36% hydrochloric acid at 80'C for 1 hour. It was subsequently cooled, filtered, and washed in 10 L of hot water. It was then dried to obtain titanyloxophthalocyanine.

A (/i-oxo)bis(phtalocyaninato titanium) synthesized in accordance with the above document PHTHALOCYANINE, C. C. Leznoff et al., 1989 (VCH Publishers. Inc.) was added to the titanyloxophthalocyanine obtained at a rate of 100 nmol of (A-oxo)bis(phtalocyaninato titanium) per 1 mol of titanyloxophthalocyanine. This mixture, 0.5 L of water, and 1.5 L of odichlorobenzene (manufactured by Kanto Chemical Co., Ltd.) were placed in a ball mill apparatus with 6.6 kg of zirconia balls (diameter 8 mm) placed inside, and the resulting mixture was milled for 24 hours. Then, the mixture was taken out using 1.5 L of acetone and 1.5 L of methanol, filtered, and washed in 1.5 L of water, followed by drying.

Next, 10 pts/wt of this (A-oxo)bis(phtalocyaninato titanium) containing titanyloxophthalocyanine, 10 pts/wt of vinyl chloride-based resin (manufactured by Nippon Xeon Co., Ltd.; MR-110), 686 pts/wt of dichloromethane, and 294 pts/wt of 1,2-dichloroethane were mixed together and ultrasonically dispersed to produce a charge generation layer coating liquid. The dip coating method was used to coat this charge generation layer coating liquid onto the above-mentioned undercoat layer in order to form a charge generation layer having a thickness of 0.2 14m. after drying. Formation of the Charge Transportation Layer pts/wt of 4-(diphenylamino)benzaldehydephenyI (2-tienyhnethyl) hydrazone (manufactured by Fuji Electric Co., Ltd.), 100 pts/wt of polycarbonate resin (manufactured by Teijin Chemicals Ltd.; PANLITE K-1300), 800 pts/wt of dichloromethane, 1 pt/wt of silane coupling agent (manufactured by Shinetsu Chemical Co., Ltd.; KP-340), and 4 pts/wt of bis (2, 4-di-tertbutylphenyl) phenylphosphonite (manufactured by Fuji Electric Co., Ltd.) were mixed together to produce a charge transportation layer coating liquid. The dip coating method was used to coat this charge transportation layer coating liquid onto the above-mentioned charge generation layer in order to form a charge transportation layer having a thickness of 20 Am after drying.

12 Example 2

A photosensitive body was manufactured in the same manner as in Example 1 except that 10 gmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 1 was used per 1 mol of titanyloxophthalocyanine.

Example 3

A photosensitive body was manufactured in the same manner as in Example 1 except that 1 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 1 was used per 1 mol of titanyloxophthalocyanine.

Example 4

A photosensitive body was manufactured in the same manner as in Example 1 except that 100 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 1 was used per 1 mol of titanyloxophthalocyanine.

Example 5

A photosensitive body was manufactured in the same manner as in Example 1 except that 300 mmol of the (1ú-oxo)bis(phtalocyaninato titanium) in Example 1 was used per 1 mol of titanyloxophthalocyanine.

Example 6

A photosensitive body was manufactured in the same manner as in Example 1 except that after addition of the (g-oxo)bis(phtalocyaninato titanium) in Example 1, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 7

A photosensitive body was manufactured in the same manner as in Example 6 except that 10jumol of the (g-oxo)bis(phtalocyaninato titanium) in Example 6 was used per 1 mol of titanyloxophthalocyanine.

Example 8

A photosensitive body was manufactured in the same manner as in Example 6 except that 1 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 6 was used per 1 mol of titanyloxophthalocyanine.

13 Example 9

A photosensitive body was manufactured in the same manner as in Example 6 except that 100 mmol of the (A-oxo)bis(phtalocyaninato titanium) in Example 6 was used per 1 mol of titanyloxophthalocyanine.

Example 10

A photosensitive body was manufactured in the same manner as in Example 6 except that 300 mmol of the (A-oxo)bis(phtalocyaninato titanium) in Example 6 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 1 A photosensitive body was manufactured in the same manner as in Example 1 except that 50 nmol of the (A-oxo)bis(phtalocyaninato titanium) in Example 1 was used per 1 mol of titanyloxophthlocyanine.

Comparative Example 2 A photosensitive body was manufactured in the same manner as in Example 1 except that 400 mmol of the k-oxo)bis(phtaloqyaninato titanium) in Example 1 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 3 A photosensitive body was manufactured in the same manner as in Example 6 except that 50 nmol of the (A-oxo)bis(phtalocyaninato titanium) in Example 6 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 4 A photosensitive body was manufactured in the same manner as in Example 6 except that 400 mmol of the (k-oxo)bis(phtalocyaninato titanium) in Example 6 was used per 1 mol of titanyloxophthalocyanine.

The electrical characteristics of the photosensitive bodies obtained as described above were measured using a static recording-paper test apparatus (manufactured by Kawaguchi Electric Works Co., Ltd.; EPA-8200). The photosensitive bodies were charged to a surface potential of -600 V in a dark environment using corotron and were left sitting for 5 14 seconds while the retention of potential (%) was measured. The results are shown in Table 2 below.

Table 2

Retention (%) Retention Example 1 98.0 Comparative Example 1 91.3 Example 2 97.3 Comparative Example 2 89.2 Example 3 97.4 Comparative Example 3 91.8 Example 4 97.3 Comparative Example 4 89.0 Example 5 97.5 Example 6 97.0 Example 7 98.3 Example 8 97.2 Example 9 97.6 Example 10 97.8 As is apparent from Table 2, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

In addition, when the (g-oxo)bis(phtalocyaninato titanium) containing titanyloxophthalocyanines used in Examples 3 to 5 and 8 to 10 were examined using the MALDI-TOF-MS analyser (manufactured by Shimazu Corp.; Kornpact MALDI IV), all of them exhibited definite peaks at the mass numbers 576 and 1136, and the mass number of 576 could be identified as titanyloxophthalocyanine molecule ions. In this case, the peak integrated intensity ratio at the mass number of 1136 was more than 10-5% of that at the mass number of 576.

Furthermore, the charge generation material, an antioxidant, and a silanecoupling material ware extracted and removed from the electrophotographic photosensitive bodies produced in Examples 3 to 5 and 8 to 10 using acetone ultrasonic bathing, and the resin was dissolved and removed from the charge transportation layer by dipping the photosensitive bodies in dichloromethane. Solutions were then prepared by dipping and dispersing the charge generation material and the charge generation material resin in dichloromethane under ultrasonic bathing, and examined using the TOF-MS analyser. The solutions all exhibited definite peaks at the mass numbers of 576 and 1136, and the mass number of 576 could be identified as titanyloxophthalocyanine molecule ions. In this case, the peak integrated intensity ratio at the mass number of 1136 was more than 10-5% of that at the mass number of 576.

Example 11

A photosensitive body was manufactured in the same manner as in Example 1 except that the (g-oxo)bis(phtalocyaninato titanium) in Example 1 was substituted with a g-oxomanganese phthalocyanine dimer synthesized pursuant to a common method.

Example 12

A photosensitive body was manufactured in the same manner as in Example 11 except that 10 gmol of the g-oxomanganese phthalocyanine dimer in Example 11 was used per 1 mol of titanyloxophthalocyanine.

Example 13

A photosensitive body was manufactured in the same manner as in Example 11 except that 1 mmol of the g-oxomanganese phthalocyanine dimer in Example 11 was used per 1 mol of titanyloxophthalocyanine.

Example 14

A photosensitive body was manufactured in the same manner as in Example 11 except that 100 mmol of the g-oxomanganese phthalocyanine dimer in Example 11 was used per 1 mol of titanyloxophthalocyanine.

Example 15

A photosensitive body was manufactured in the same manner as in Example 11 except that 300 mmol of the g-oxomanganese phthalocyanine dimer in Example 11 was used per 1 mol of titanyloxophthalocyanine.

16 Example 16

A photosensitive body was manufactured in the same manner as in Example 11 except that, after addition of the g-oxomanganese phthalocyanine dimer in Example 11, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 17

A photosensitive body was manufactured in the same manner as in Example 16 except that 10 gmol of the g-oxomanganese phthalocyanine dimer in Example 16 was used per 1 mol of titanyloxophthalocyanine.

Example 18

A photosensitive body was manufactured in the same manner as in Example 16 except that 1 mmol of the g-oxomanganese phthalocyanine dirner in Example 16 was used per 1 mol of titanyloxophthalocyanine.

Example 19

A photosensitive body was manufactured in the same manner as in Example 16 except that 100 mmol of the g-oxornanganese phthalocyanine dirner in Example 16 was used per 1 mol of titanyloxophthalocyanine.

Example 20

A photosensitive body was manufactured in the same manner as in Example 16 except that 300 mmol of the g-oxomanganese phthalocyanine dimer in Example 16 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 5 A photosensitive body was manufactured in the same manner as in Example 11 except that 50 nmol of the g-oxomanganese phthalocyanine dimer in Example 11 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 6 A photosensitive body was manufactured in the same manner as in Example 11 except that 400 mmol of the ii-oxomanganese phthalocyanine dimer in Example 11 was used per 1 mol of titanyloxophthalocyanine.

17 Comparative Example 7 A photosensitive body was manufactured in the same manner as in Example 16 except that 50 nmol of the A-oxomanganese phthalocyanine dimer in Example 16 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 8 A photosensitive body was manufactured in the same manner as in Example 16 except that 400 mmol of the A-oxomanganese phthalocyanine dimer in Example 16 was used per I mol of titanyloxophthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 3.

Table 3

Retention (%) Retention Example 11 98.2 Comparative Example 5 91.8 Example 12 97.1 Comparative Example 6 89.1 Example 13 97.8 Comparative Example 7 91.2 Example 14 97.2 Comparative Example 8 88.7 Example 15 97.6 Example 16 97.3 Example 17 98.1 Example 18 97.7 Example 19 97.4 Example 20 97.9 As is apparent from Table 3, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 21

A photosensitive body was manufactured in the same manner as in Example 1 except that the titanyloxophthalocyanine in Example 1 was substituted with iron phthalocyanine synthesized pursuant to a common method.

18 Example 22 A photosensitive body was manufactured in the same manner as in Example 21 except that 10 gmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 21 was used per 1 mol of iron phthalocyanine.

Example 23 A photosensitive body was manufactured in the same manner as in Example 21 except that 1 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 21 was used per 1 mol of iron phthalocyanine.

Example 24 A photosensitive body was manufactured in the same manner as in Example 21 except that 100 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 21 was used per 1 mol of iron phthalocyanine.

Example 25 A photosensitive body was manufactured in the same manner as in Example 21 except that 300 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 21 was used per 1 mol of iron phthalocyanine.

Example 26

A photosensitive body was manufactured in the same manner as in Example 21 except that after addition of the (g-oxo)bis(phtalocyaninato titanium) in Example 21, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 27 A photosensitive body was manufactured in the same manner as in Example 26 except that 10 gmol of the (1ú-oxo)bis(phtalocyaninato titanium) in Example 26 was used per 1 mol of iron phthalocyanine.

Example 28 A photosensitive body was manufactured in the same manner as in Example 26 except that 1 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 26 was used per 1 mol of iron phthalocyanine.

19 Example 29

A photosensitive body was manufactured in the same manner as in Example 26 except that 100 mmol of the (ii-oxo)bis(phtalocyaninato titanium) in Example 26 was used per 1 mol of iron phthalocyanine.

Example 30

A photosensitive body was manufactured in the same manner as in Example 26 except that 300 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 26 was used per 1 mol of iron phthalocyanine.

Comparative Example 9 A photosensitive body was manufactured in the same manner as in Example 21 except that 50 nmol of the (,u-oxo)bis(phtalocyaninato titanium) in Example 21 was used per 1 mol of iron phthalocyanine.

Comparative Example 10 A photosensitive body was manufactured in the same manner as in Example 21 except that 400 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 21 was used per 1 mol of iron phthalocyanine.

Comparative Example 11 A photosensitive body was manufactured in the same manner as in Example 26 except that 50 nmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 26 was used per 1 mol of iron phthalocyanine.

Comparative Example 12 A photosensitive body was manufactured in the same manner as in Example 26 except that 400 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 26 was used per 1 mol of iron phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 4.

Table 4

Retention (%) Retention Example 21 95.6 Comparative Example 9 89.2 Example 22 96.1 Comparative Example 10 87.9 Example 23 95.7 Comparative Example 11 88.2 Example 24 95.4 Comparative Example 12 87.4 Example 25 95.0 Example 26 95.3 Example 27 94.6 Example 28 95.2 Example 29 95.6 Example 30 95.1 As is apparent from Table 4, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 31

A photosensitive body was manufactured in the same manner as in Example 21 except that the (ii-oxo)bis(phtalocyaninato titanium) in Example 21 was substituted with a jx-oxoiron phthalocyanine dimer synthesized pursuant to a common method.

Example 32

A photosensitive body was manufactured in the same manner as in Example 31 except that 10 Amol of the A-oxoiron phthalocyanine dimer in Example 31 was used per 1 mol of iron phthalocyanine.

Example 33

A photosensitive body was manufactured in the same manner as in Example 31 except that 1 mmol of the /.k-oxoiron phthalocyanine dimer in Example 31 was used per 1 mol of iron phthalocyanine.

21 Example 34

A photosensitive body was manufactured in the same manner as in Example 31 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 31 was used per 1 mol of iron phthalocyanine.

Example 35

A photosensitive body was manufactured in the same manner as in Example 31 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 31 was used per 1 mol of iron phthalocyanine.

Example 36

A photosensitive body was manufactured in the same manner as in Example 31 except that, after addition of the g-oxoiron phthalocyanine dimer in Example 31, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 37

A photosensitive body was manufactured in the same manner as in Example 36 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 36 was used per 1 mol of iron phthalocyanine.

Example 38

A photosensitive body was manufactured in the same manner as in Example 36 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 36 was used per 1 mol of iron phthalocyanine.

Example 39

A photosensitive body was manufactured in the same manner as in Example 36 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 36 was used per 1 mol of iron phthalocyanine.

Example 40

A photosensitive body was manufactured in the same manner as in Example 36 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 36 was used per 1 mol of iron phthalocyanine.

22 Comparative Example 13 A photosensitive body was manufactured in the same manner as in Example 31 except that 50 nmol of the bt-oxoiron phthalocyanine dimer in Example 31 was used per 1 mol of iron phthalocyanine.

Comparative Example 14 A photosensitive body was manufactured in the same manner as in Example 31 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 31 was used per 1 mol of iron phthalocyanine.

Comparative Example 15 A photosensitive body was manufactured in the same manner as in Example 36 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 36 was used per 1 mol of iron phthalocyanine.

Comparative Example 16 A photosensitive body was manufactured in the same manner as in Example 36 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 36 was used per 1 mol of iron phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 5.

Table 5

Retention (%) Retention Example 31 95.3 Comparative Example 13 88.2 Example 32 95.2 Comparative Example 14 87.1 Example 33 95.8 Comparative Example 15 88.4 Example 34 95.2 Comparative Example 16 87.7 Example 35 94.9 Example 36 95.3 Example 37 95.1 Example 38 94.7 Example 39 95.3 Example 40 95.4 23 As is apparent from Table 5, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 41

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with iron (11) 1, 2, 3, 4, 8, 9, 10, 11, 15, 16, 17, 18, 22, 23, 24, 25hexadecafluoro-29H, 31H-phthalocyanine (hereafter simply referred to as Iluoroiron phthalocyanine") synthesized pursuant to a common method.

Example 42

A photosensitive body was manufactured in the same manner as in Example 41 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 41 was used per 1 mol of fluoroiron phthalocyanine.

Example 43

A photosensitive body was manufactured in the same manner as in Example 41 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 41 was used per 1 mol of fluoroiron phthalocyanine.

Example 44

A photosensitive body was manufactured in the same manner as in Example 41 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 41 was used per 1 mol of fluoroiron phthalocyanine.

Example 45

A photosensitive body was manufactured in the same manner as in Example 41 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 41 was used per 1 mol of fluoroiron phthalocyanine.

Example 46

A photosensitive body was manufactured in the same manner as in Example 41 except that after addition of the g-oxoiron phthalocyanine dimer in Example 41, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

24 Example 47

A photosensitive body was manufactured in the same manner as in Example 46 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 46 was used per 1 mol of fluoroiron phthalocyanine.

Example 48

A photosensitive body was manufactured in the same manner as in Example 46 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 46 was used per 1 mol of fluoroiron phthalocyanine.

Example 49

A photosensitive body was manufactured in the same manner as in Example 46 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 46 was used per 1 mol of fluoroiron phthalocyanine.

Example 50

A photosensitive body was manufactured in the same manner as in Example 46 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 46 was used per 1 mol of fluoroiron phthalocyanine.

Comparative Example 17 A photosensitive body was manufactured in the same manner as in Example 41 except that 50 nmol of the g-oxoiron phthaloeyanine dimer in Example 41 was used per 1 mol of fluoroiron phthalocyanine.

Comparative Example 18 A photosensitive body was manufactured in the same manner as in Example 41 except that 400 mmol of the g-oxoiron phthaloeyanine dimer in Example 41 was used per 1 mol of fluoroiron phthalocyanine.

Comparative Example 19 A photosensitive body was manufactured in the same manner as in Example 46 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 46 was used per 1 mol of fluoroiron phthalocyanine.

Comparative Example 20 A photosensitive body was manufactured in the same manner as in Example 46 except that 400 mmol of theu-oxoiron phthalocyanine dimer in Example 46 was used per 1 mol of fluoroiron phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 6.

Table 6

Retention (%) Retention Example 41 96.1 Comparative Example 17 89.4 Example 42 95.4 Comparative Example 18 88.0 Example 43 95.8 Comparative Example 19 89.2 Example 44 96.0 Comparative Example 20 88.3 Example 45 95.4 Example 46 95.5 Example 47 95.5 Example 48 95.2 Example 49 95.3 Example 50 95.9 As is apparent from Table 6, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 51

A photosensitive body was manufactured in the same manner as in Example 21 except that the iron phthalocyanine in Example 21 was substituted with zirconium phthalocyanine synthesized pursuant to a common method.

26 Example 52 A photosensitive body was manufactured in the same manner as in Example 51 except that 10 gmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 51 was used per 1 mol of zirconium phthalocyanine.

Example 53 A photosensitive body was manufactured in the same manner as in Example 51 except that 1 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 51 was used per 1 mol of zirconium phthalocyanine.

A photosensitive body was manufactured in the same manner as in Example 51 except that 100 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 51 was used per 1 mol of zirconium phthalocyanine.

Example 55 A photosensitive body was manufactured in the same manner as in Example 51 except that 300 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 51 was used per 1 mol of zirconium phthalocyanine.

Example 56

A photosensitive body was manufactured in the same manner as in Example 51 except that after addition of the (g-oxo)bis(phtalocyaninato titanium) in Example 51, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 57 A photosensitive body was manufactured in the same manner as in Example 56 except that 10 limol of the (g-oxo)bis(phtalocyaninato titanium) in Example 56 was used per 1 mol of zirconium phthalocyanine.

Example 58 A photosensitive body was manufactured in the same manner as in Example 56 except that 1 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 56 was used per 1 mol of zirconium phthalocyanine.

27 Example 59

A photosensitive body was manufactured in the same manner as in Example 56 except that 100 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 56 was used per 1 mol of zirconium phthalocyanine.

Example 60

A photosensitive body was manufactured in the same manner as in Example 56 except that 300 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 56 was used per 1 mol of zirconium phthalocyanine.

Comparative Example 21 A photosensitive body was manufactured in the same manner as in Example 51 except that 50 nmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 51 was used per 1 mol of zirconium phthalocyanine.

Comparative Example 22 A photosensitive body was manufactured in the same manner as in Example 51 except that 400 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 51 was used per 1 mol of zirconium phthalocyanine.

Comparative Example 23 A photosensitive body was manufactured in the same manner as in Example 56 except that 50 nmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 56 was used per 1 mol of zirconium phthalocyanine.

Comparative Example 24 A photosensitive body was manufactured in the same manner as in Example 56 except that 400 mmol of the (g-oxo)bis(phtalocyaninato titanium) in Example 56 was used per 1 mol of zirconium phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 7.

28 Table 7

Retention Retention Example 51 95.3 Comparative Example 21 88.9 Example 52 95.7 Comparative Example 22 88.1 Example 53 95.8 Comparative Example 23 88.2 Example 54 95.0 Comparative Example 24 87.7 Example 55 95.6 Example 56 95.0 Example 57 95.5 Example 58 95.1 Example 59 95.4 Example 60 5.6 As is apparent from Table 7, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 61

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with vanadium phthalocyanine synthesized pursuant to a common method.

Example 62

A photosensitive body was manufactured in the same manner as in Example 61 except that 10 Amol of the g-oxoiron phthalocyanine dimer in Example 61 was used per 1 mol of vanadium phthalocyanine.

Example 63

A photosensitive body was manufactured in the same manner as in Example 61 except that 1 mmol of the A-oxoiron phthalocyanine dimer in Example 61 was used per 1 mol of vanadium phthalocyanine.

29 Example 64

A photosensitive body was manufactured in the same manner as in Example 61 except that 100 mmol of the bú-oxoiron phthalocyanine dimer in Example 61 was used per 1 mol of vanadium phthalocyanine.

Example 65

A photosensitive body was manufactured in the same manner as in Example 61 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 61 was used per 1 mol of vanadium phthalocyanine.

Example 66

A photosensitive body was manufactured in the same manner as in Example 61 except that, after addition of the g-oxoiron phthalocyanine dimer in Example 61, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 67

A photosensitive body was manufactured in the same manner as in Example 66 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 66 was used per 1 mol of vanadium phthalocyanine.

Example 68

A photosensitive body was manufactured in the same manner as in Example 66 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 66 was used per 1 mol of vanadium phthalocyanine.

Example 69

A photosensitive body was manufactured in the same manner as in Example 66 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 66 was used per 1 mol of vanadium phthalocyanine.

Example 70

A photosensitive body was manufactured in the same manner as in Example 66 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 66 was used per 1 mol of vanadium phthalocyanine.

Comparative Example 25 A photosensitive body was manufactured in the same manner as in Example 61 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 61 was used per 1 mol of vanadium phthalocyanine.

Comparative Example 26 A photosensitive body was manufactured in the same manner as in Example 61 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 61 was used per 1 mol of vanadium phthalocyanine.

Comparative Example 27 A photosensitive body was manufactured in the same manner as in Example 66 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 66 was used per 1 mol of vanadium phthalocyanine.

Comparative Example 28 A photosensitive body was manufactured in the same manner as in Example 66 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 66 was used per 1 mol of vanadium phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 8.

Table 8

Retention (%) Retention Example 61 95.5 Comparative Example 25 88.9 Example 62 95.3 Comparative Example 26 88.6 Example 63 95.3 Comparative Example 27 88.7 Example 64 95.7 Comparative Example 28 88.4 Example 65 95.0 Example 66 95.8 Example 67 95.1 Example 68 95.2 Example 69 95.4 Example 70 95.6 31 As is apparent from Table 8, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 71

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with niobium phthalocyanine synthesized pursuant to a common method.

Example 72

A photosensitive body was manufactured in the same manner as in Example 71 except that 10 gmol of the 1ú-oxoiron phthalocyanine dimer in Example 71 was used per 1 mol of niobium phthalocyanine.

Example 73

A photosensitive body was manufactured in the same manner as in Example 71 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 71 was used per 1 mol of niobium phthalocyanine.

Example 74

A photosensitive body was manufactured in the same manner as in Example 71 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 71 was used per 1 mol of niobium phthalocyanine.

Example 75

A photosensitive body was manufactured in the same manner as in Example 71 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 71 was used per 1 mol of niobium phthalocyanine.

Example 76

A photosensitive body was manufactured in the same manner as in Example 71 except that, after addition of the g-oxoiron phthalocyanine dimer in Example 71, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

32 Example 77

A photosensitive body was manufactured in the same manner as in Example 76 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 76 was used per 1 mol of niobium phthalocyanine.

Example 78

A photosensitive body was manufactured in the same manner as in Example 76 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 76 was used per 1 mol of niobium phthalocyanine.

*Example 79

A photosensitive body was manufactured in the same manner as in Example 76 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 76 was used per 1 mol. of niobium phthalocyanine.

Example 80

A photosensitive body was manufactured in the same manner as in Example 76 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 76 was used per 1 mol of niobium phthalocyanine.

Comparative Example 29 A photosensitive body was manufactured in the same manner as in Example 71 except that 50 nmol of the ii-oxoiron phthalocyanine dimer in Example 71 was used per 1 mol of niobium phthalocyanine.

Comparative Example 30 A photosensitive body was manufactured in the same manner as in Example 71 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 71 was used per 1 mol of niobium phthalocyanine.

Comparative Example 31 A photosensitive body was manufactured in the same manner as in Example 76 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 76 was used per 1 mol of niobium phthalocyanine.

33 Comparative Example 32 A photosensitive body was manufactured in the same manner as in Example 76 except that 400 mmol of the A-oxoiron phthalocyanine dimer in Example 76 was used per 1 mol of niobiurn phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 9.

Table 9

Retention (%) Retention Example 71 95.0 Comparative Example 29 89.3 Example 72 95.1 Comparative Example 30 88.1 Example 73 94.8 Comparative Example 31 88.2 Example 74 95.5 Comparative Example 32 89.7 Example 75 95.7 Example 76 95.2 Example 77 95.4 Example 78 94.9 Example 79 95.1 Example 80 95.2 As is apparent from Table 9, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 81

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with indiurn phthalocyanine synthesized pursuant to a common method.

34 Example 82

A photosensitive body was manufactured in the same manner as in Example 81 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 81 was used per 1 mol of indium phthalocyanine.

Example 83

A photosensitive body was manufactured in the same manner as in Example 81 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 81 was used per 1 mol of indium phthalocyanine.

Example 84 A photosensitive body was manufactured in the same manner as in Example 81

except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 81 was used per 1 mol of indium phthalocyanine.

Example 85

A photosensitive body was manufactured in the same manner as in Example 81 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 81 was used per 1 mol of indium phthalocyanine.

Example 86

A photosensitive body was manufactured in the same manner as in Example 81 except that, after addition of the g-oxoiron phthalocyanine dimer in Example 81, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 87

A photosensitive body was manufactured in the same manner as in Example 86 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 86 was used per 1 mol of indium phthalocyanine.

Example 88

A photosensitive body was manufactured in the same manner as in Example 86 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 86 was used per 1 mol of indium phthalocyanine.

Example 89

A photosensitive body was manufactured in the same manner as in Example 86 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 86 was used per 1 mol of indium. phthalocyanine.

Example 90

A photosensitive body was manufactured in the same manner as in Example 86 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 86 was used per 1 mol. of indium. phthalocyanine.

Comparative Example 33 A photosensitive body was manufactured in the same manner as in Example 81 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 81 was used per 1 mol of indium phthalocyanine.

Comparative Example 34 A photosensitive body was manufactured in the same manner as in Example 81 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 81 was used per 1 mol of indium. phthalocyanine.

Comparative Example 35 A photosensitive body was manufactured in the same manner as in Example 86 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 86 was used per 1 mol of indium phthalocyanine.

Comparative Example 36 A photosensitive body was manufactured in the same manner as in Example 86 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 86 was used per 1 mol of indium phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 10.

36 Table 10

Retention (%) Retention Example 81 95.3 Comparative Example 33 89.4 Example 82 95.0 Comparative Example 34 88.6 Example 83 94.9 Comparative Example 35 89.2 Example 84 95.2 Comparative Example 36 89.7 Example 85 95.4 Example 86 95.1 Example 87 95.5 Example 88 95.2 Example 89 95.4 Example 90 95.3 As is apparent from Table 10, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 91

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with gallium phthalocyanine synthesized pursuant to a common method.

Example 92

A photosensitive body was manufactured in the same manner as in Example 91 except that 10 /.kmol of the g-oxoiron phthalocyanine dimer in Example 91 was used per 1 mol of gallium phthalocyanine.

Example 93

A photosensitive body was manufactured in the same manner as in Example 91 except that 1 mmol of the A-oxoiron phthalocyanine dimer in Example 91 was used per 1 mol of gallium phthalocyanine.

37 Example 94

A photosensitive body was manufactured in the same manner as in Example 91 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 91 was used per 1 mol of gallium phthalocyanine.

Example 95

A photosensitive body was manufactured in the same manner as in Example 91 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 91 was used per 1 mol of gallium phthalocyanine.

Example 96

A photosensitive body was manufactured in the same manner as in Example 91 except that, after addition of the 1ú-oxoiron phthalocyanine dimer in Example 91, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 97

A photosensitive body was manufactured in the same manner as in Example 96 except that 10 limol of the g-oxoiron phthalocyanine dimer in Example 96 was used per 1 mol of gallium phthalocyanine.

Example 98

A photosensitive body was manufactured in the same manner as in Example 96 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 96 was used per 1 mol of gallium phthalocyanine.

Example 99

A photosensitive body was manufactured in the same manner as in Example 96 except that 100 mmol of the 1ú-oxoiron phthalocyanine dimer in Example 96 was used per 1 mol of gallium phthalocyanine.

Example 100

A photosensitive body was manufactured in the same manner as in Example 96 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 96 was used per 1 mol of gallium phthalocyanine.

38 Comparative Example 37 A photosensitive body was manufactured in the same manner as in Example 91 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 91 was used per 1 mol of gallium phthalocyanine.

Comparative Example 38 A photosensitive body was manufactured in the same manner as in Example 91 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 91 was used per 1 mol of gallium phthalocyanine.

Comparative Example 39 A photosensitive body was manufactured in the same manner as in Example 96 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 96 was used per 1 mol of gallium phthalocyanine.

Comparative Example 40 A photosensitive body was manufactured in the same manner as in Example 96 except that 400 mmol of the ii-oxoiron phthalocyanine dimer in Example 96 was used per 1 mol of gallium phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 11.

Table 11

Retention (%) Retention Example 91 95.5 Comparative Example 37 88.4 Example 92 95.0 Comparative Example 38 88.1 Example 93 95.2 Comparative Example 39 88.2 Example 94 95.4 Comparative Example 40 87.9 Example 95 95.1 Example 96 95.2 Example 97 95.0 Example 98 95.3 Example 99 94.9 Example 100 95.2 39 As is apparent from Table 11, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 101

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with germanium phthalocyanine synthesized pursuant to a common method.

Example 102

A photosensitive body was manufactured in the same manner as in Example 101 except that 10 gmol of the A-oxoiron phthalocyanine dimer in Example 101 was used per 1 mol of germanium phthalocyanine.

Example 103

A photosensitive body was manufactured in the same manner as in Example 101 except that 1 mmol of the ji-oxoiron phthalocyanine dimer in Example 101 was used per 1 mol of germanium phthalocyanine.

Example 104

A photosensitive body was manufactured in the same manner as in Example 101 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 101 was used per 1 mol of germanium phthalocyanine.

Example 105

A photosensitive body was manufactured in the same manner as in Example 101 except that 300 mmol of the g-oxoiron phthalocyanine dirner in Example 101 was used per 1 mol of germanium phthalocyanine.

Example 106

A photosensitive body was manufactured in the same manner as in Example 101 except that, after addition of the p-oxoiron phthalocyanine dimer in Example 101, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 107

A photosensitive body was manufactured in the same manner as in Example 106 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 106 was used per 1 mol of germanium phthalocyanine.

Example 108

A photosensitive body was manufactured in the same manner as in Example 106 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 106 was used per 1 mol of germanium phthalocyanine.

Example 109

A photosensitive body was manufactured in the same manner as in Example 106 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 106 was used per 1 mol of germanium phthalocyanine.

Example 110

A photosensitive body was manufactured in the same manner as in Example 106 except that 300 mmol of theu-oxoiron phthalocyanine dimer in Example 106 was used per 1 mol of germanium phthalocyanine.

Comparative Example 41 A photosensitive body was manufactured in the same manner as in Example 101 except that 50 ranol of the g-oxoiron phthalocyanine dimer in Example 101 was used per 1 mol of germanium phthalocyanine.

Comparative Example 42 A photosensitive body was manufactured in the same manner as in Example 101 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 101 was used per 1 mol of germanium phthalocyanine.

Comparative Example 43 A photosensitive body was manufactured in the same manner as in Example 106 except that 50 mnol of the g-oxoiron phthalocyanine dimer in Example 106 was used per 1 mol of germanium phthalocyanine.

41 Comparative Example 44 A photosensitive body was manufactured in the same manner as in Example 106 except that 400 mmol of the /x-oxoiron phthalocyanine dimer in Example 106 was used per 1 mol of germanium phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 12.

Table 12

Retention (%) Retention Example 101 95.2 Comparative Example 41 88.3 Example 102 95.0 Comparative Example 42 88.0 Example 103 95.3 Comparative Example 43 88.5 Example 104 95.2 Comparative Example 44 88.7 Example 105 95.4 Example 106 94.8 Example 107 95.1 Example 108 95.0 Example 109 95.2 Example 110 95.3 As is apparent from Table 12, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 111

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with tin phthalocyanine synthesized pursuant to a common method.

42 Example 112

A photosensitive body was manufactured in the same manner as in Example 111 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 111 was used per 1 mol of tin phthalocyanine.

Example 113

A photosensitive body was manufactured in the same manner as in Example 111 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 111 was used per 1 mol of tin phthalocyanine.

Example 114

A photosensitive body was manufactured in the same manner as in Example 111 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 111 was used per 1 mol of tin phthalocyanine.

Example 115

A photosensitive body was manufactured in the same manner as in Example 111 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 111 was used per 1 mol of tin phthalocyanine.

Example 116

A photosensitive body was manufactured in the same manner as in Example 111 except that, after addition of the g-oxoiron phthalocyanine dimer in Example 111, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 117

A photosensitive body was manufactured in the same manner as in Example 116 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 116 was used per 1 mol of tin phthalocyanine.

Example 118

A photosensitive body was manufactured in the same manner as in Example 116 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 116 was used per 1 mol of tin phthalocyanine.

43 Example 119

A photosensitive body was manufactured in the same manner as in Example 116 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 116 was used per 1 mol of tin phthalocyanine.

Example 120

A photosensitive body was manufactured in the same manner as in Example 116 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 116 was used per 1 mol of tin phthalocyanine.

Comparative Example 45 A photosensitive body was manufactured in the same manner as in Example 111 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 111 was used per 1 mol of tin phthalocyanine.

Comparative Example 46 A photosensitive body was manufactured in the same manner as in Example 111 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 111 was used per 1 mol of tin phthalocyanine.

Comparative Example 47 A photosensitive body was manufactured in the same manner as in Example 116 except that 50 nmol of the g-oxoiron phthalocyanine ditner in Example 116 was used per 1 mol of tin phthalocyanine.

Comparative Example 48 A photosensitive body was manufactured in the same manner as in Example 116 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 116 was used per 1 mol of tin phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 13.

44 Table 13

Retention Retention Example 111 95.2 Comparative Example 45 89.0 Example 112 95.0 Comparative Example 46 88.2 Example 113 95.1 Comparative Example 47 89.2 Example 114 95.4 Comparative Example 48 88.5 Example 115 95.2 Example 116 95.5 Example 117 95.1 Example 118 94.9 Example 119 95.2 Example 120 95.1 As is apparent from Table 13, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 121

A photosensitive body was manufactured in the same manner as in Example 11 except that the titanyloxophthalocyanine in Example 11 was substituted with manganese phthalocyanine synthesized pursuant to a common method.

Example 122

A photosensitive body was manufactured in the same manner as in Example 121 except that 10 pmol of the jk-oxomanganese phthalocyanine dimer in Example 121 was used per 1 mol of manganese phthalocyanine.

Example 123

A photosensitive body was manufactured in the same manner as in Example 121 except that 1 mmol of the,t-oxomanganese phthalocyanine dimer in Example 121 was used per 1 mol of manganese phthalocyanine.

Example 124

A photosensitive body was manufactured in the same manner as in Example 121 except that 100 mmol of the g-oxomanganese phthalocyanine dimer in Example 121 was used per 1 mol of manganese phthalocyanine.

Example 125

A photosensitive body was manufactured in the same manner as in Example 121 except that 300 mmol of the g-oxomanganese phthalocyanine dimer in Example 121 was used per 1 mol of manganese phthalocyanine.

Example 126

A photosensitive body was manufactured in the same manner as in Example 121 except that, after addition of the g-oxomanganese phthalocyanine dimer in Example 121, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 127

A photosensitive body was manufactured in the same manner as in Example 126 except that 10 gmol of the g-oxomanganese phthalocyanine dimer in Example 126 was used per 1 mol of manganese phthalocyanine.

Example 128

A photosensitive body was manufactured in the same manner as in Example 126 except that 1 mmol of the ii-oxomanganese phthalocyanine dimer in Example 126 was used per 1 mol of manganese phthalocyanine.

Example 129

A photosensitive body was manufactured in the same manner as in Example 126 except that 100 mmol of the g-oxomanganese phthalocyanine dimer in Example 126 was used per 1 mol of manganese phthalocyanine.

Example 130

A photosensitive body was manufactured in the same manner as in Example 126 except that 300 mmol of the g-oxomanganese phthalocyanine dimer in Example 126 was used per 1 mol of manganese phthalocyanine.

46 Comparative Example 49 A photosensitive body was manufactured in the same manner as in Example 121 except that 50 nmol of the g-oxomanganese phthalocyanine dimer in Example 121 was used per 1 mol of manganese phthalocyanine.

Comparative Example 50 A photosensitive body was manufactured in the same manner as in Example 121 except that 400 mmol of the g-oxemanganese phthalocyanine dimer in Example 121 was used per 1 mol of manganese phthalocyanine.

Comparative Example 51 A photosensitive body was manufactured in the same manner as in Example 126 except that 50 nmol of the g-oxomanganese phthalocyanine dirner in Example 126 was used per 1 mol of manganese phthalocyanine.

Comparative Example 52 A photosensitive body was manufactured in the same manner as in Example 126 except that 400 mmol of the g-oxomanganese phthalocyanine dimer in Example 126 was used per 1 mol of manganese phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 14.

Table 14

Retention (%) Retention Example 121 95.2 Comparative Example 49 88.9 Example 122 95.1 Comparative Example 50 88.3 Example 123 94.8 Comparative Example 51 89.2 Example 124 95.2 Comparative Example 52 88.7 Example 125 95.2 Example 126 95.4 Example 127 95.0 Example 128 95.1 Example 129 95.3 Example 130 95.2 47 As is apparent from Table 14, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 131

A photosensitive body was manufactured in the same manner as in Example 1 except that the (A-oxo)bis(phtalocyaninato titanium) in Example 1 was substituted with a A-dysprosium phthalocyanine dimer synthesized pursuant to a common method.

Example 132

A photosensitive body was manufactured in the same manner as in Example 131 except that 10 Amol of the A-dysprosiurn phthalocyanine dirner in Example 131 was used per 1 mol of titanyloxophthalocyanine.

Example 133

A photosensitive body was manufactured in the same manner as in Example 131 except that 1 mmol of the A-dysprosium phthalocyanine dimer in Example 131 was used per 1 mol of titanyloxophthalocyanine.

Example 134

A photosensitive body was manufactured in the same manner as in Example 131 except that 100 mmol of the A-dysprosium phthalocyanine dimer in Example 131 was used per 1 mol of titanyloxophthalocyanine.

Example 135

A photosensitive body was manufactured in the same manner as in Example 131 except that 300 mmol of the A-dysprosium phthalocyanine dimer in Example 131 was used per 1 mol of titanyloxophthalocyanine.

Example 136

A photosensitive body was manufactured in the same manner as in Example 131 except that, after addition of the A-dysprosium phthalocyanine dimer in Example 131, the solution was acid-pasted in 96% sulphuric: acid, washed in water, and then dried.

48 Example 137

A photosensitive body was manufactured in the same manner as in Example 136 except that 10 gmol of the ii-dysprosium phthalocyanine dimer in Example 136 was used per 1 mol of titanyloxophthalocyanine.

Example 138

A photosensitive body was manufactured in the same manner as in Example 136 except that 1 mmol of the g-dysprosium phthalocyanine dimer in Example 136 was used per 1 mol of titanyloxophthalocyanine.

Example 139

A photosensitive body was manufactured in the same manner as in Example 136 except that 100 mmol of the g-dysprosium phthalocyanine dimer in Example 136 was used per 1 mol of titanyloxophthalocyanine.

Example 140

A photosensitive body was manufactured in the same manner as in Example 136 except that 300 mmol of the g-dysprosium phthalocyanine dimer in Example 136 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 53 A photosensitive body was manufactured in the same manner as in Example 131 except that 50 nmol of the g-dysprosium phthalocyanine dimer in Example 131 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 54 A photosensitive body was manufactured in the same manner as in Example 131 except that 400 mmol of the g-dysprosium phthalocyanine dimer in Example 131 was used per 1 mol of titanyloxophthalocyanine.

Comparative Example 55 A photosensitive body was manufactured in the same manner as in Example 136 except that 50 nmol of the g-dysprosium phthalocyanine dimer in Example 136 was used per 1 mol. of titanyloxophthalocyanine.

49 Comparative Example 56 A photosensitive body was manufactured in the same manner as in Example 136 except that 400 mmol of the g-dysprosium phthalocyanine dimer in Example 136 was used per 1 mol of titanyloxophthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 15.

Table 15

Retention (%) Retention Example 131 98.0 Comparative Example 53 91.1 Example 132 97.5 Comparative Example 54 90.8 Example 133 97.3 Comparative Example 55 90.7 Example 134 97.6 Comparative Example 56 91.3 Example 135 97.5 Example 136 97.8 Example 137 97.1 Example 138 97.2 Example 139 97.5 Example 140 97.6 As is apparent from Table 15, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

Example 141

A photosensitive body was manufactured in the same manner as in Example 31 except that the iron phthalocyanine in Example 31 was substituted with nonmetallic phthalocyanine synthesized pursuant to a common method.

Example 142

A photosensitive body was manufactured in the same manner as in Example 141 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 141 was used per 1 mol of nonmetallic phthalocyanine.

Example 143

A photosensitive body was manufactured in the same manner as in Example 141 except that 1 mmol of the g-oxoiron phthalocyanine dimer in Example 141 was used per 1 mol of nonmetallic phthalocyanine.

Example 144

A photosensitive body was manufactured in the same manner as in Example 141 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 141 was used per 1 mol of nonmetallic phthalocyanine.

Example 145

A photosensitive body was manufactured in the same manner as in Example 141 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 141 was used per 1 mol of nonmetallic phthalocyanine.

Example 146

A photosensitive body was manufactured in the same manner as in Example 141 except that, after addition of the g-oxoiron phthalocyanine dimer in Example 141, the solution was acid-pasted in 96% sulphuric acid, washed in water, and then dried.

Example 147

A photosensitive body was manufactured in the same manner as in Example 146 except that 10 gmol of the g-oxoiron phthalocyanine dimer in Example 146 was used per 1 mol of nonmetallic phthalocyanine.

Example 148

A photosensitive body was manufactured in the same manner as in Example 146 except that 1 mmol of the ii-oxoiron phthalocyanine dimer in Example 146 was used per 1 mol of nonmetallic phthalocyanine.

51 Example 149

A photosensitive body was manufactured in the same manner as in Example 146 except that 100 mmol of the g-oxoiron phthalocyanine dimer in Example 146 was used per 1 mol of nonmetallic phthalocyanine.

Example 150

A photosensitive body was manufactured in the same manner as in Example 146 except that 300 mmol of the g-oxoiron phthalocyanine dimer in Example 146 was used per 1 mol of nonmetallic phthalocyanine.

Comparative Example 57 A photosensitive body was manufactured in the same manner as in Example 141 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 141 was used per 1 mol. of nonmetallic phthalocyanine.

Comparative Example 58 A photosensitive body was manufactured in the same manner as in Example 141 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 141 was used per 1 mol of nonmetallic phthalocyanine.

Comparative Example 59 A photosensitive body was manufactured in the same manner as in Example 146 except that 50 nmol of the g-oxoiron phthalocyanine dimer in Example 146 was used per 1 mol of nonmetallic phthalocyanine.

Comparative Example 60 A photosensitive body was manufactured in the same manner as in Example 146 except that 400 mmol of the g-oxoiron phthalocyanine dimer in Example 146 was used per 1 mol of nonmetallic phthalocyanine.

The electrical characteristics of the photosensitive bodies obtained in the above manner were measured as described above to determine the retention (%). The results are shown in Table 16.

52 Table 16

Retention (%) Retention Example 141 96.4 Comparative Example 57 91.0 Example 142 96.6 Comparative Example 58 89.4 Example 143 96.3 Comparative Example 59 90.7 Example 144 96.7 Comparative Example 60 89.7 Example 145 96.1 Example 146 96.5 Example 147 96.9 Example 148 96.6 Example 149 96.4 Example 150 96.2 As is apparent from Table 16, all the examples produced good results due to their high retentions, whereas all the comparative examples exhibited a lower retention than the examples.

According to the present invention, an electrophotographic photosensitive body having high retention can be obtained by adding at least a phthalocyanine compound to a photoconductive layer of a conductive substrate and also adding a phthalocyanine dimer compound thereto as a photoconductive material in a manner such that 100 nmol or more and 300 mmol or less of phthalocyanine dimer compound is used per 1 mol of phthalocyanine compound.

In addition, according to the present invention, a method for manufacturing an electrophotographic photosensitive body having high retention can be obtained by adding a phthalocyanine compound and a phthalocyanine dimer compound to a photoconductive layer-forming coating liquid on a conductive substrate in a manner such that the content of the phthalocyanine dimer compound is 100 nmol or more and 300 Mmol or less per 1 mol of the phthalocyanine.

53

Claims

1. An electrophotographic photosensitive body having a photosensitive layer formed on a conductive substrate, the photosensitive layer containing a phthalocyanine compound as a photoconductive material, characterized in that:

the content of the phthalocyanine dimer compound in the layer having said phthalocyanine compound is 100 nmol or more and 300 mmol or less per 1 mol of the phthalocyanine compound.

2. An electrophotographic photosensitive body according to Claim 1 characterized in that the phthalocyanine compound forming said phthalocyanine dimer compound is titanyloxophthalocyanine compound. 3. An electrophotographic photosensitive body according to Claim 1 characterized in that said phthalocyanine compound is nonmetallic phthalocyanine.

4. An electrophotographic photosensitive body according to Claim 2 characterized in that in matrix assisted laser desorptionflonization time of flight mass spectrometry, peaks occur at mass numbers of 576 and 1136, and the peak area integrated intensity at the mass number of 1136 is 10-5% or more and 30% or less of that at the mass number of 576.

5. An electrophotographic photosensitive body according to Claim 1 characterized in that a central element of the phthalocyanine compound forming said phthalocyanine dimer compound is a transition metal.

6. An electrophotographic photosensitive body according to Claim 5 characterized in that said transition metal is selected from a group comprising titanium, vanadium, chromium, manganese, iron, cobalt, nickel, zirconium, niobium, molybdenum, rhodium, cerium, neodymium, samarium, europium, and tungsten.

7. An electrophotographic photosensitive body according to Claim 1 characterized in that the central element of the phthalocyanine compound forming said phthalocyanine dimer compound is selected from a group comprising indium, gallium, aluminium, germanium, tin, antimony, lead, bismuth, silicon, and phosphorous.

54 8. An electrophotographic photosensitive body according to any of Claims I to 7 characterized in that said phthalocyanine compound and the phthalocyanine compound forming said phthalocyanine dimer compound is represented by the following formula:

R3 R6 2 4 R9 R 8 7 R 15 R 16, I R9 R10 (1) R13 I R14 where M denotes a diatomic element in the Ia family, or an element that can assume an oxidized state of + 2 or more, or an oxide, hydroxide, halide, or alcohol salt of said element; and R1 to R16 each denote a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an ester group, an alkyl group, an alkenyl group, an alkoxyl group, an allyl group, or an allyloxyl group, and may be the same or different from one another. 9. An electrophotographic photosensitive body according to Claim 1 characterized in that said phthalocyanine dimer compound has a structure of l.k-oxo dimer compound. 10. An electrophotographic photosensitive body according to Claim 9 characterized in that said phthalocyanine dimer compound has a Pc-M-0-M-Pc structure where Pc denotes a phthalocyanine compound, M denotes an element having an m6dation number of +3 or more, and 0 denotes an oxygen atom. 11. An electrophotographic photosensitive body according to Claim 1 characterized in that said phthalocyanine dimer compound has a structure of A-dimer compound. 12. An electrophotographic photosensitive body according to Claim 11 characterized in that said phthalocyanine dimer compound has a Pc-M-Pc structure where Pc denotes a phthalocyanine compound, and M denotes an element having an oxidation number of +3 or more.

13. A method for manufacturing an electrophotographic photosensitive body according to Claim 1, the method having the step of forming a photosensitive layer by coating, onto a conductive substrate, a coating liquid containing a charge generation material, characterized in that: said coating liquid contains a phthalocyanine compound and a phthalocyanine dimer compound and in that the content of the phthalocyanine dimer compound is 100 nmol or more and 300 mmol or less per 1 mol of the phthalocyanine compound.

Amendments to the claims have been filed as follows CLAIMS 1. An electrophotographic photosensitive body having a photosensitive layer formed on a conductive substrate, the photosensitive layer containing a phthalocyanine compound as a photoconductive material, characterized in that:

2. An electrophotographic photosensitive body according to Claim 1 characterized in that the phthalocyanine compound forming said phthalocyanine dimer compound is titanyloxophthalocyanine compound.

3. An electrophotographic photosensitive body according to Claim 1 characterized in that said phthalocyanine compound is 29H, 31H-phthalocyanine.

4. An electrophotographic photosensitive body according to Claim 2 characterized in that in matrix assisted laser desorption/ionization time of flight mass spectrometry, peaks occur at mass numbers of 576 and 1136, and the peak area integrated intensity at the mass number of 1136 is 10-5% or more and 30% or less of that at the mass number of 576.

SI.

8. An electrophotographic photosensitive body according to any of Claims 1 to 7 characterized in that said phthalocyanine compound and the phthalocyanine compound forming said phthalocyanine dimer compound is represented by the following formula:

R3 R 6 R 2 4 5 01 0 R 16 0 1 10 (1) R 1 q R - R1 R..

R14 0' where M denotes a diatomic element in the la family, or an element that can assume an oxidized state of +2 or more, or an oxide, hydroxide, halide, or alcohol salt of said element; and R1 to R16 each denote a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an ester group, an alkyl group, an alkenyl group, an alkoxyl group, an allyl group, or an allyloxyl group, and may be the same or different from one another.

9. An electrophotographic photosensitive body according to Claim 1 characterized in that said phthalocyanine dimer compound has a structure of g-oxo dimer compound.

10. An electrophotographic photosensitive body according to Claim 9 characterized in that said phthalocyanine dimer compound has a Pc-M-0-M-Pc structure where Pc denotes a phthalocyanine compound, M denotes an element having an oxidation number of +3 or more, and 0 denotes an oxygen atom.

11. An electrophotographic photosensitive body according to Claim 1 characterized in that said phthalocyanine dimer compound has a structure of g-dimer compound.

12. An electrophotographic photosensitive body according to Claim 11 characterized in that said phthalocyanine dimer compound has a Pc-M-Pc structure where Pc denotes a phthalocyanine compound, and M denotes an element having an oxidation number of +3 or more.

I St.

--104

13. A method for manufacturing an electrophotographic photosensitive -1 body according to Claim 1, the method having the step of forming a photosensitive layer by coating, onto a conductive substrate, a coating liquid containing a charge generation material, characterized in that: said coating liquid contains a phthalocyanine compound and a phthalocyanine dimer compound and in that the content of the phthalocyanine dimer compound is 100 nmol or more and 300 mmol or less per 1 mol of the phthalocyanine compound.