JPH0772640A - Electrophotographic photoreceptor - Google Patents

Abstract

PURPOSE:To provide the electrophotographic photoreceptor having higher hardness, improved mechanical strength, high sensitivity and high durability by incorporating specific charge transferable monomers and binder resin into a photosensitive layer and polymerizing these charge transferable monomers. CONSTITUTION:One or >=2 kinds of the charge transferable monomers having the polymerizable double bonds of carbon-carbon expressed by formula I, formula II or formula III and the binder resin are incorporated into the photosensitive layer of the electrophotographic photoreceptor provided with the photosensitive layer on a conductive substrate. The charge transferable monomers are polymerized by heat or light energy. In the formulas I to III, R1 denote hydrogen, methyl group; Ar1; Ar2 denote substd. or unsubstd. bivalent arom. hydrocarbon groups, substd. or unsubstd. bivalent condensed polycyclic hydrogen groups; Ar3, Ar4 denote substd. or unsubstd. univalent arom. hydrocarbon groups, substd. or unsubstd. univalent condensed hydrogen groups; Y denotes -CnH2n-, -CH=CH-, etc.; Z denotes -O-, -OCnH2n, etc.,; (n) denotes an integer up to 10; m1, m2 denote 0 or 1.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor having high hardness, high mechanical strength, high sensitivity and high durability.

[0002]

2. Description of the Related Art In recent years, organic photoconductors (OPC) have been used in copying machines,
It is often used in printers. These OPCs have a structure in which a charge generation layer (CGL) and a charge transfer layer (CTL) are sequentially stacked. In CTL, a low molecular weight transfer material (CTM) is dissolved in a binder resin at a certain concentration to form a film. Addition of CTM lowers the mechanical strength inherent in the binder resin, and the CTL film becomes brittle and has a low tensile strength. This decrease in mechanical strength causes wear, scratches, peeling, cracks, and the like of the photoconductor.

On the other hand, polyvinylcarbazole, polyvinylanthracene, polyvinylpyrene, M.I. Stolkka
Et al. (J. Polym. Sci. VOL 21.969)
Polymer proposed in Japan, Japan Hard Copy8
9'P. Attempts have been made to increase the molecular weight of CTL such as the vinyl polymer of hydrazone described in 67, but the CTL film is still brittle and the mechanical strength has not been improved. Further, the polymer CTM is not sufficient in terms of sensitivity, residual potential, etc. and has low durability as a photoreceptor. It is also proposed to disperse CTM in a binder resin and then cure the binder resin, but the CTM concentration is 30 to 50.
%, The curing reaction is not sufficient, and CTM is
It came out and was worn out and the problem has not been solved. As another method, a silicone-containing polymer is added to the photosensitive layer (described in JP-A-61-219049 and 62-205357) and a fluorine-containing polymer is added (JP-A-50-232).
31, the same 61-116362, the same 61-204633,
61-270768), addition of silicone resin fine particles and fluororesin fine particles (JP-A-63-65449).
Described in JP-A-60-1).
No. 77349) has been proposed, but the compatibility with CTM or binder resin is poor, and phase separation occurs in the CTL film to form an opaque film, which deteriorates the electrical characteristics and has not solved the problem.

[0004]

The present invention is based on the C of CTM.
After the formation of TL, a high molecular weight by light or heat energy was measured, and the pseudo-IPN (Interpenetrating Pol) incorporated in the binder resin matrix was measured.
It is an object of the present invention to provide an electrophotographic photoconductor having high hardness and improved mechanical strength, and high sensitivity and high durability due to ymer Network).

[0005]

According to the present invention, in an electrophotographic photosensitive member having a photosensitive layer provided on a conductive support, the photosensitive layer is represented by the following general formula I (Formula 1) and general formula II (Formula 1) 2),
Alternatively, one or more charge-transporting monomers having a carbon-carbon polymerizable double bond represented by the general formula III (Chemical Formula 3) and a binder resin are contained, and the charge is applied by heat or light energy. Provided is an electrophotographic photoreceptor characterized by polymerizing a mobile monomer.

[Chemical 1]

[Chemical 2]

[Chemical 3] (In the formula, R1: hydrogen, methyl group Ar1, Ar2: substituted or unsubstituted divalent aromatic hydrocarbon group, substituted or unsubstituted divalent condensed polycyclic hydrogen group, Ar3, Ar4: substituted or unsubstituted Monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent condensed polycyclic hydrogen group, Y: -CnH2n-, -CH = CH-, -CAr1 = CH
-Z: -O-, -OCnH2n-, -OCnH2nO- n: an integer of 1 to 10 m1, m2: 0 or 1
) Further, there is provided the electrophotographic photoreceptor, wherein the binder resin of the charge transferable monomer is a homopolymerization or copolymerization resin having a repeating unit represented by the following general formula IV (Formula 4). Done

[Chemical 4] Further, the electrophotographic photosensitive member is provided in which the binder resin of the charge transferable monomer is a homopolymerized or copolymerized vinyl resin having a repeating unit represented by the following general formula V (Formula 5). To be done.

[Chemical 5] (In the formula, R1: hydrogen, methyl group, X: aryl group, COOR2 (R2 is an alkyl group having 1 to 3 carbon atoms, an aryl group,))

The compounds represented by the above general formula I (Formula 1) to general formula III (Formula 3) are high charge carrier transfer compounds, and are monomers having a triphenylamine skeleton which is a hopping site for charge carriers. is there. These monomers can be polymerized with a polymerization initiator such as radicals and ions to obtain a high molecular weight compound, but a single film has insufficient mechanical strength, and a blend of the single high molecular weight compound and the binder resin is not compatible. It was an opaque film with poor solubility. Therefore, after uniformly forming the monomer and the binder resin, the monomer is polymerized to form a pseudo-IPN film together with the binder resin and the like to form a transparent and uniform photosensitive layer. Since the film before polymerization forms a solid solution of the monomer and binder resin, the monomer is immobilized and cannot move. However, the film is heated to 60 ° C or more by the energy of heat and light and moves. Radicals, which are active species for initiating polymerization, are generated, and move in the film of the solid solution in which motion has started to polymerize the monomers. It is considered that it is difficult to obtain a long-distance polymer at the initiation of polymerization, and the degree of polymerization is -20 or less. Further, it is conceivable that the radical, which is an active species at the initiation of the polymerization, is chain-transferred to the binder resin and activated to bond with the monomer.
This is suggested by the fact that the polymerized film is improved in the pencil hardness by two orders, and it is also considered that the polymerized film is soluble in dichloroethane and has a large gel content. Polyvinylcarbazole as a polymer transfer material, M.I. Stolk
The polyacryl transfer material of a) has a lower mobility than the low molecular dispersion type and has a large electric field strength dependency. It is considered that this is due to the slow motion of the molecules derived from the polymer. Therefore, in the polymerization of the monomer of the present invention in a solid solution, the polymer is entangled with the binder resin and the pseudo IPN so that it does not easily come off from the photosensitive layer, the hardness is improved, the abrasion resistance is improved, and the degree of polymerization is suppressed. It can be said that the molecular motion of the site is an ideal system that does not impair the electrical properties as small molecules do.
Specific examples of guest monomers that are polymerized by light or heat energy in the binder resin matrix as the host are shown in Tables 1 to 3 below.

[Specific Examples of Compounds of Formula I (Chemical Formula 1)]

[Table 1- (1)]

[Table 1- (2)]

[Table 1- (3)]

[Table 1- (4)]

[Table 1- (5)]

[Table 1- (6)]

[Table 1- (7)]

[Table 1- (8)]

[Table 1- (9)]

[Table 1- (10)]

[Table 1- (11)]

[Specific examples of the compound represented by the general formula II (formula 2)]

[Table 2- (1)]

[Table 2- (2)]

[Table 2- (3)]

[Table 2- (4)]

[Specific Examples of Compounds of Formula III (Chemical Formula 3)]

[Table 3]

The binder resin used in the present invention for dispersing and binding the charge transfer monomers represented by the general formulas I (Chemical formula 1) to III (Chemical formula 3) may be one kind or two or more kinds of resins. Used as a mixture. As such a binder resin, a polycarbonate resin, a phenoxy resin, a polyester resin, or a polysulfone resin having a repeating unit represented by the general formula IV (Formula 4) is preferable, and these resins are tenacious ductile glassy polymers, It has a high impact strength and is resistant to notch scratches. The average molecular weight is 1
10,000 to 100,000, preferably 20,000 to 60,000, GP
The number average molecular weight degree of polymerization is 50 to 400, preferably 80 to 300, when measured by polystyrene equivalent molecular weight distribution. As another advantage of these resins, a clear transparent film having excellent compatibility with the charge transfer monomers represented by the general formulas I to III is obtained and excellent electrophotographic properties are exhibited.

Table 4 below shows specific examples of the binder resin represented by the general formula (IV).

[Table 4- (1)]

[Table 4- (2)]

[Table 4- (3)]

The binder resin of the present invention may be a copolymer having the repeating unit represented by the above general formula IV (Formula 4). Specific examples of the copolymer are shown in Table 5 below.

[Table 5- (1)]

[Table 5- (2)]

Further, the binder resin of the charge transfer monomer represented by the general formulas I (formula 1) to III (formula 3) used in the present invention has a repeating unit represented by the general formula V. Characterized by being a homopolymerized or copolymerized vinyl resin, these binder resins have good film properties, good compatibility with the charge transfer monomers represented by the general formulas I to III, and a clear film can be obtained. Good electrophotographic properties. Specific examples of these vinyl resins include polystyrene, polymethylmethacrylate, styrene-methylmethacrylate copolymer, styrene-methylmethacrylate-butylmethacrylate copolymer, styrene-
A butadiene copolymer is mentioned. The molecular weight of the vinyl resin is 10,000 or more, preferably 100,000 or more.

In the present invention, the case where the charge transfer monomer and the binder resin are mixed and polymerized will be described. The ratio of the charge transfer monomer represented by the general formulas I to III and the binder resin such as the resin having the repeating units represented by the general formulas IV to V is 10 parts by weight with respect to 10 parts of the charge transfer monomer. 5 to 50 parts of binder resin, preferably 7 to 30 parts of binder resin to 10 parts of charge transfer monomer. If it is 7 parts or less, the coating film becomes brittle, easily scratched, and the adhesiveness becomes poor and peeling due to dents occurs, which is not preferable, and if it is 30 parts or more, sensitivity is insufficient and residual potential is accumulated, which is not preferable. A charge transfer monomer reaction initiator may or may not be used, and in the case of heat curing, 2,5-dimethylhexane 2,5-dihydroperoxide, dicumyl peroxide, benzoyl is used as a reaction initiator. Peroxide, t-butylcumyl peroxide,
Peroxides such as 2,5-dimethyl-2,5-di (peroxybenzoyl) hexyne-3, azo compounds such as azobisisobutylnitrile, or Michler's ketone, benzoin isopropyl ether, 1- as a photo-curing initiator A ketone system such as hydroxycyclohexyl phenyl ketone is used. Addition amount is 0.00 relative to monomer
Used at about 5 to 0.5 parts by weight. Examples of the solvent include ketones such as methyl ethyl ketone and cyclohexanone, esters such as ethyl acetate and butyl acetate, ethers such as tetrahydrofuran and dioxane, dichloroethane,
A halogen type such as chlorobenzene and an aromatic type such as toluene and xylene are used. Thermal polymerization is 80-170
It is carried out at 20 ° C. for 20 to 60 minutes, and when the reaction initiator is added, the aging time until the coating of the added solution is shortened, and it is preferably carried out under the above-mentioned conditions under nitrogen stream. If the amount of the reaction initiator added is 0.001 to 0.1 mol with respect to the monomer, and if it is more than that, the decomposed product of the reaction initiator remains in the photosensitive layer and deteriorates the electrical characteristics. By photopolymerization, the acrylic system is non-catalytic, and the reaction is initiated by irradiation of ultraviolet rays. A mercury lamp is used as a light source, and energy of 40 to 120 W / cm is applied for 1 to 2 minutes. The addition of the catalyst accelerates the polymerization rate and shortens the irradiation time. The monomer of the present invention is active with respect to ultraviolet rays and sufficiently polymerizes even without a catalyst.

In the present invention, low molecular weight CTM can be used in combination with CTL. Examples of such CTMs include oxazole derivatives and oxadiazole derivatives (Japanese Patent Laid-Open Publication No.
2-139065, JP-A-52-139066), benzidine derivative (described in JP-B-58-32372), imidazole derivative, triphenylamine derivative (described in JP-A-1-77839), α-phenyl Stilbene derivatives (described in JP-A-57-73075), hydrazone derivatives (JP-A-55-15495)
5, ibid 55-156954, ibid 55-52063, ibid 5
6-81850), triphenylmethane derivative (described in JP-B-51-10983), anthracene derivative (described in JP-A-51-94829), and styryl derivative (JP-A-56-29245). Same 5
8-198043), carbazole derivatives (described in JP-A-58-58552), pyrene derivatives (described in JP-A-2-94812), and the like. The addition amount is preferably 0.1 to 10% by weight with respect to the charge transfer monomer.

The CGL is formed of a charge generating material (CGM) alone or CGM and a binder resin. CG
Examples of M include C.I. I. No. Condensed polycyclic quinone compounds such as 59300 Vat Orange 3, C.I. I. N
o. Perylene compounds such as 38001, azo pigments having a carbazole skeleton (JP-A-53-95033), azo pigments having a stilbene skeleton (JP-A-53-13822).
9), azo pigments having a triphenylamine skeleton (JP-A-53-132547), azo pigments having a dibenzothiophene skeleton (JP-A-54-21728), azo pigments having an oxadiazole skeleton (JP-A-54-54). 1274
2), an azo pigment having a fluorenone skeleton (JP-A-54)
22834), azo pigments having a bisstilbene skeleton (JP-A-54-17733), azo pigments having a distyryl oxadiazole skeleton (JP-A-54-2129),
Azo pigments having a distyrylcarbazole skeleton (JP-A-54-17734) and trisazo pigments having a carbazole skeleton (JP-A-57-195767 and 57-195).
768), azo pigments having an anthraquinone skeleton (JP-A-57-202545), squarium dyes, metal or metal-free phthalocyanines, selenium and selenium alloys,
For example, a-silicon can be used.

In the present invention, these general formulas I to III are used.
A binder resin such as a resin having a repeating unit represented by the general formulas IV and V, and CGM as a conductive support, such as aluminum, copper, nickel, and electrically conductive metals and alloys such as stainless steel and ceramics. The surface of the inorganic insulating material and the organic insulating material such as polyester, polyimide, phenol resin, nylon resin, paper, etc. is subjected to a method such as vacuum deposition, sputtering, spray coating, etc.
Drum-shaped, sheet-shaped, and plate-shaped materials that have been electroconductively coated with an electrically conductive substance such as aluminum, copper, nickel, stainless steel, carbon black, tin oxide, indium oxide, antimony oxide, and conductive titanium oxide. To provide a photosensitive layer.

When the photosensitive layer is a negative charging type photoreceptor in which CGL and CTL are sequentially laminated, CGL is a ketone solvent such as methyl ethyl ketone or cyclohexanone, and CGM is a ketone solvent.
Tetrahydrofuran, dioxane, etc. ether type, ethyl acetate, etc. ester type, dichloroethane, chlorobenzene, etc. halogen type, toluene, xylene, etc. aromatic solvent etc. The diameter is preferably 0.3 μm or less. At this time, a binder resin may be added, and examples of the resin include polyvinyl butyral, polyvinyl acetal, cellulose derivative, phenol resin, epoxy resin and acrylic polyol. When the dispersion does not contain a binder resin, an intermediate layer is provided to prevent charge injection from the conductive support. Examples of the binder resin for the intermediate layer include polyamide, polyacrylic anilide, casein, vinyl chloride-vinyl acetate-maleic acid copolymer, and phenol resin. As the CGL coating method, a conventionally known method such as a dipping method, a spray method, or a roll method is applied. The film thickness is 0.05 to 5 μm, preferably 0.05 to 1 μm. The CTL is applied by the above-mentioned coating method and reacted or photoreacted at 60 to 200 ° C. to provide a CTL having a film thickness of 15 to 50 μm. Further, it is preferable to use a low molecular weight CTM together, and by adding 0.01 to 1 part by weight to 10 parts by weight of the charge transfer monomer, higher sensitivity can be achieved.

In the case of a positive charging type photoconductor in which CTL and CGL are sequentially laminated on a conductive support, since the surface layer has CGL, the charge transfer monomers represented by the general formulas I to III and the general formula IV are used. , V is contained in CGL. The CGM is pulverized and dispersed with a binder resin, or after the CGM is pulverized and dispersed, the binder resin and the charge transfer monomer are added, and 0.5 to 10 μm of CGL is provided on the CTL of 15 to 50 μm by the coating method. . At this time, the charge transfer monomer of the general formulas I to III and the general formula IV,
The ratio of CGM to a binder resin such as a resin having a repeating unit represented by V is preferably a charge transfer monomer: binder resin: CGM = 10: 7 to 30: 2 to 10 by weight. This CGL can contain, as an additive, a polyether compound such as polyethylene glycol, a cyclic ether compound such as a crown ether, and a phosphite ester compound such as tridecyl phosphite. It is to prevent this, and it is preferable to add the charge generating material: additive = 10: 0.1 to 5 weight ratio.

CGM and the general formulas I to I on a conductive support.
Also in a single-layer positively charged photoreceptor comprising a charge transfer monomer of formula II and a binder resin such as a resin having repeating units represented by formulas IV and V, the charge transfer monomer of formulas I to III: binder Resin: CGM = 10: 7-30:
The photosensitive layer is formed in a weight ratio of 2 to 10, and the above-mentioned antistatic deterioration additive can be added.

Binder resins such as resins having the charge transfer monomers of the general formulas I to III and the repeating units represented by the general formulas IV and V can also be used in the protective layer, and the conventional low molecular weight CTM is used as the binder resin. A protective layer having a thickness of 0.5 to 2 μm is provided on the dispersed CTL.

[0022]

EXAMPLES The present invention will be described in more detail below with reference to examples.

Example 1 A polyamide resin (CM-8000 manufactured by Toray Industries, Inc.) was spray coated on an aluminum cylinder having a stroke of 80 mm and a stroke of 340 mm and dried to form an intermediate layer having a thickness of 0.3 μm. An azo pigment having a structure represented by the following chemical formula 6 was pulverized with cyclohexanone and dispersed, and a dispersion liquid was spray coated and dried to provide 0.2 μm CGL.

[Chemical 6] Next, the following CTL liquid is applied by the dipping method, and at 120 ° C. for 20 minutes.
It was dried for a minute and provided with a 25 μm CTL. This photosensitive member was irradiated and cured for 2 minutes while rotating at a light intensity of a high pressure mercury lamp of 120 W / cm. Polycarbonate resin (C-1400 manufactured by Teijin Chemicals) 100 parts

[Chemical 7] Silicone oil (KF-50 manufactured by Shin-Etsu Silicone Co., Ltd.) 1 part Dichloromethane 800 parts This photoconductor was attached to the device shown in JP-A-60-100167 and rotated at 1000 rpm, and a negative voltage of 6 Kv was applied in the dark. The electric potential (Vm) when discharged and applied for 20 seconds was obtained, after which the discharge was stopped and dark decay was performed for 20 seconds, and then the electric potential (Vo) at that time was further irradiated with tungsten light with a light amount of 26 Lux and a slit width of 6 mm from Vo. Sensitivity was determined by setting the amount of halving E1 / 2 and the amount of halving E1 / 10. The potential after 20 seconds was set to Vr. The thus prepared photoconductor was mounted on FT-4820 manufactured by Ricoh Co., Ltd., and a durability test of 100,000 sheets was performed. The initial dark portion potential (VD) was set to 800V and the light portion potential (VL) was set to 80V. Vm: 1320V, Vo: 1060V, E1 / 2: 0.
82 Lux · sec, E1 / 10: 2.35 Lux / s
ec, Vr: 5V VD after 100,000 sheets: 780V, VL: 90V, wear amount:
0.8 μm

Examples 2 to 11 In the same manner as in Example 1, the intermediate layer and CGL were provided, and then Table 6 below was used.
In the same manner as in Example 1, the charge transfer monomer and the binder resin shown in 1 above were coated, dried, and irradiated with a high pressure mercury lamp to prepare a photoreceptor.

[Table 6]

The electrical characteristics and durability test results of the above photosensitive member are shown in Table 7 as in Example 1.

[Table 7]

Comparative Example 1 Similar to Example 1, an intermediate layer and CGL were provided and the following CT was applied.
Apply L liquid by dipping method and dry at 120 ° C for 20 minutes.
A 3 μm CTL was provided. [CTL liquid] 100 parts of polycarbonate resin (C-1400 manufactured by Teijin Chemicals)

[Chemical 8] Silicone oil (KF-50 manufactured by Shin-Etsu Silicone Co., Ltd.) 1 part Dichloromethane 800 parts

Comparative Examples 2 to 4 Photoconductors were prepared in the same manner as in Comparative Example 1 except that only the binder resin of CTL was changed.

The electrical characteristics and the amount of wear after durability are shown in Table 8 below.

[Table 8]

In Examples 1 to 9, clear images were obtained at the initial stage and after 100,000 sheets. In Example 10, after 100,000 sheets, background stains and white streaks and black streaks were generated in the halftone image. In Example 11, the standard notch of the developing bias caused the background streaks. Disappears. However, in Examples 10 and 11, the abrasion resistance is significantly improved as compared with Comparative Examples 3 and 4 using the same binder resin. In Comparative Example 1, after 100,000 sheets, background stains and white streaks and black streaks occurred in the halftone image, and Comparative Example 2 was similar to Example 11, but was inferior in electrical characteristics. In Comparative Examples 3 and 4, the background stain was generated on about 40,000 to 50,000 sheets, and even after the development bias was controlled, the background stain was generated. As described above, it can be seen that the amount of wear was significantly improved by reacting the monomer in the binder resin.

Example 12 C was added to an aluminum cylinder having a stroke of 80φ and a stroke of 340 mm.
Apply the TL solution by the dipping method and dry at 120 ° C for 20 minutes.
A 0 μm CTL was provided. [CTL liquid] 100 parts of polycarbonate resin (C-1400 manufactured by Teijin Chemicals)

[Chemical 9] Silicone oil (KF-50 manufactured by Shin-Etsu Silicone Co., Ltd.) 1 part Dichloromethane 1000 parts Then, the following CGL solution was applied by a spray method at 150 ° C.
After drying for 30 minutes and reacting, 3 μm CGL was provided. [CGL liquid]

[Chemical 6] Polyethylene glycol monostearyl 2 parts (Ionet 400MS Sanyo Kasei Co., Ltd.) Cyclohexanone 440 parts was pulverized with a ball mill for 72 hours, dispersed, 400 parts of methyl ethyl ketone was added, and dispersed again for 3 hours to prepare a mill base. 20 parts of cyclohexanone: methyl ethyl ketone = 1: 1 by weight mixed solvent, 20 parts of mill base, No.
32 parts of the charge transfer monomer of No. 32, No. 32. 11 parts 2 parts of polycarbonate resin, 1 part of 2,2-bis (4,4-di-t-butylperoxycyclohexyl) propane (Perkadox 12-XL25 Kayaku Akzo Co., Ltd.) was let down to prepare a coating solution. did.

Examples 13 to 15 In the same manner as in Example 12, CTL was provided and CG shown in Table 9 below.
A dispersion liquid of M and a binder resin was prepared in the same manner as in Example 12 and coated by a spray method to provide 3 μm of CGL (the reactive monomer and the reaction catalyst were the same as in Example 12).

[Table 9]

Comparative Example 5 20 parts of the mill base prepared in Example 12 was mixed with 20 parts of cyclohexanone: MEK = 1: 1 weight ratio solvent, 2 parts of CTM used in Comparative Example 1, No. 11 binder resins 2
Part of the solution was let down to obtain a coating solution, which was applied onto CTL similar to that in Example 12 by a spray method and dried at 150 ° C. for 30 minutes to obtain a CGL photoreceptor having a film thickness of 3 μm.

The photoconductors of Examples 12 to 15 and Comparative Example 5 were mounted in the same apparatus as described above, and a positive voltage of 6 Kv was applied thereto. Attached to -6550, dark area potential (VD) 800
V and bright part potential (VL) were set to 80 V, and a durability test of 50,000 sheets was conducted. The results are shown in Table 10.

[Table 10] The reaction product of the present invention was clear even at the initial stage after 50,000 sheets, but in the case of Comparative Example 5, black stripes were generated due to partial scratches reaching the CTL, and the image was partially shaded. Unevenness was confirmed.

Example 16 10 parts of the CGL mill base used in Example 12 were treated with No. Three
10 parts of the monomer, 12 parts of the No. 42 binder resin,
5,2-bis (4,4 di-t-butylperoxycyclohexyl) propane (Percadox 12-XL25 Kayaku Akzo) 5 parts, cyclohexanone 10 parts, MEK
A coating solution containing 10 parts was prepared and applied to an aluminum cylinder of 80φ, 340 mm by a spray method at 150 ° C., 30
After drying for 30 minutes and curing, a single-layer photosensitive layer having a thickness of 30 μm was provided. Similarly to the above, as a result of measuring electric characteristics by positive charging, Vm: 1
240V, Vo: 1000V, E1 / 2: 1.06Lu
x ・ Sec, E1 / 10: 2.56Lux ・ Sec, V
It was r: 10V. In addition, this photosensitive member is referred to as the FT-6.
When the durability test of 10,000 sheets was performed at 550, there was no wear,
The image was clear with no background stains due to sensitivity deterioration.

Example 17 Similar to Example 1, an intermediate layer and CGL were provided on an 80φ, 340 mm aluminum cylinder, and then the CTL of Example 12 was used.
The liquid was applied by a dipping method and dried to provide a 20 μm CTL. No. 39 parts binder resin, NO.
63 parts of charge transfer monomer, the above-mentioned Perkadox 12
0.2 part of -XL25 was made into a 6% solution with a mixed solvent of tetrahydrofuran / cyclohexanone 1/1, and was applied by a spray method, dried at 150 ° C. for 30 minutes, and cured to form a protective layer of 3 μm. The electrical characteristics were the same as in Example 1 except that a negative voltage of 6 KV was applied. As a result, Vm: 1380 V, Vo: 1
180V, E1 / 2: 0.8 Lux · Sec, E1 / 1
0: 1.6Lux · Sec, Vr: 10V, and when the above-mentioned photoconductor was subjected to a durability test of 10,000 sheets with the FT-4820, it was found that there was no abrasion, and there were abnormalities due to white lines, black lines, and filming. No images were confirmed.

[0035]

As is clear from the above examples and comparative examples, the electrophotographic photoreceptor having a photosensitive layer obtained by reacting the charge transfer monomer of the present invention with a binder resin by light and heat is It is a highly sensitive and highly durable photoreceptor with excellent abrasion resistance.

Claims (3)

[Claims] 1. An electrophotographic photosensitive member having a photosensitive layer provided on a conductive support, wherein the photosensitive layer has the following general formula I:
One or more charge transfer monomers having a carbon-carbon polymerizable double bond represented by the general formula II (Formula 2) or the general formula III (Formula 3) and a binder resin are contained. An electrophotographic photoreceptor characterized in that the charge transfer monomer is polymerized by heat or light energy. [Chemical 1] [Chemical 2] [Chemical 3] (In the formula, R1: hydrogen, methyl group Ar1, Ar2: substituted or unsubstituted divalent aromatic hydrocarbon group, substituted or unsubstituted divalent condensed polycyclic hydrogen group, Ar3, Ar4: substituted or unsubstituted Monovalent aromatic hydrocarbon group, substituted or unsubstituted monovalent condensed polycyclic hydrogen group, Y: -CnH2n-, -CH = CH-, -CAr1 = CH
-Z: -O-, -OCnH2n-, -OCnH2nO- n: an integer of 1 to 10 m1, m2: 0 or 1
) 2. The binder resin of the charge transferable monomer is a homopolymer or copolymer resin having a repeating unit represented by the following general formula IV (Chemical formula 4). Electrophotographic photoreceptor. [Chemical 4] 3. The binder resin of the charge transfer monomer is a homopolymerized or copolymerized vinyl resin having a repeating unit represented by the following general formula V (formula 5). Electrophotographic photoreceptor. [Chemical 5] (In the formula, R1: hydrogen, methyl group, X: aryl group, COOR2 (R2 is an alkyl group having 1 to 3 carbon atoms, an aryl group,))