JP6191174B2 - Photoconductor, image forming apparatus, and process cartridge - Google Patents

Description

An embodiment of the present invention relates to a photosensitive member, an image forming apparatus and a process cartridge.

  In recent years, information processing system machines using an electrophotographic system have been remarkably developed. In particular, laser printers and digital copiers that record information with light after converting the information into digital signals have significantly improved image quality and reliability. Furthermore, these have been applied to laser printers or digital copiers capable of full-color printing by fusing with high-speed technology. For this reason, the photoreceptor is required to achieve both high image quality and high durability.

  As the photoreceptor, an organic photoreceptor (OPC) is generally widely applied. The layer structure of the organic photoreceptor is roughly divided into a single layer structure and a function separation type stacked structure.

  A highly reliable charging method in the electrophotographic process is based on corona discharge, and this method is adopted in most copying machines and printers.

  Patent Document 1 discloses an electrophotographic photosensitive member in which a photosensitive layer is provided on a conductive substrate. At this time, the photosensitive layer contains a naphthalene tetracarboxylic acid derivative represented by the general formula [3], which is an electron transfer agent.

  However, there is a problem that image blur occurs when used for a long time.

  On the other hand, Patent Document 2 discloses a dicarboximide represented by the formula (Ia).

  An object of one embodiment of the present invention is to provide a photoconductor capable of suppressing the occurrence of image blur even when used for a long period of time, in view of the problems of the related art.

  In one embodiment of the present invention, in a photoreceptor, a photosensitive layer containing a charge generation material and an electron transport material is formed on a conductive support, and the electron transport material has the general formula

Wherein R ₁ and R ₄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R ₂ and R ₃ are each independently A hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, wherein R ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted group; R ₂ and R ₃ may together form a ring, and X is a single bond , a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group . is there.)

  According to an embodiment of the present invention, it is possible to provide a photoconductor that can suppress the occurrence of image blur even when used for a long period of time.

It is sectional drawing which shows an example of the layer structure of a photoreceptor. It is sectional drawing which shows the other example of the laminated constitution of a photoreceptor. It is sectional drawing which shows the other example of the laminated constitution of a photoreceptor. 1 is a schematic diagram illustrating an example of an image forming apparatus. It is the schematic which shows the other example of an image forming apparatus. It is the schematic which shows an example of a process cartridge. It is an infrared transmission spectrum of 2,3-thiophene dicarboxylic acid anhydride. It is an infrared transmission spectrum of N- (1-methylhexyl) -2,3-thiophenedicarboxylic acid imide. It is an infrared transmission spectrum of N- (3-trifluoromethylphenyl) -2,3-thiophene dicarboxylic acid imide. It is an infrared transmission spectrum of N- (2-trifluoromethylphenyl) -2,3-thiophene dicarboxylic acid imide. It is an infrared transmission spectrum of 5-bromo-N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide. It is an infrared transmission spectrum of the compound represented by Chemical formula (1-9). It is an infrared transmission spectrum of the compound represented by Chemical formula (1-15). It is an infrared transmission spectrum of a compound denoted by a chemical formula (1-4). It is an infrared transmission spectrum of a compound denoted by a chemical formula (1-12). It is an infrared transmission spectrum of the compound represented by Chemical formula (1-14). 2 is an X-ray diffraction spectrum of oxotitanium phthalocyanine.

  Next, the form for implementing this invention is demonstrated.

  FIG. 1 shows an example of the layer structure of the photoreceptor.

  In the photoreceptor (10), a charge generation layer (35) and a charge transport layer (37) are sequentially laminated on a conductive support (31). At this time, the charge transport layer (37) includes a binder resin and an electron transport material, and the electron transport material includes a compound represented by the general formula (1). Thereby, even if it uses for a long period of time, generation | occurrence | production of an image blur can be suppressed.

  The reason why image blurring can be suppressed even when used for a long time is not clear at present, but the imide group contained in the compound represented by the general formula (1) is strongly basic. Since it is a base, it is presumed to be caused by a neutralizing effect that electrically neutralizes ozone considered to be a causative substance of image blur. Furthermore, since the sulfur atom contained in the compound represented by the general formula (1) has a high electron density, it exhibits an excellent neutralization effect and charge transport function due to a synergistic effect with the basic effect of the imide group. It is estimated that In addition, the compound represented by the general formula (1) can further improve the sensitivity when used in combination with other charge transport materials, and can further suppress the occurrence of image blur even when used for a long time. Can do.

  In addition, since the compound represented by the general formula (1) is an electron transport material, it is preferable that the charge transport layer (37) further includes a hole transport material. Thereby, the photoreceptor (10) can cope with bipolar charging.

  The order in which the charge generation layer (35) and the charge transport layer (37) are stacked may be reversed.

  The compound represented by the general formula (1) can be synthesized, for example, as follows. First, thiophene-2,3-dicarboxylic acid derivative (A) is reacted at 50 to 200 ° C. in acetic anhydride to synthesize thiophene-2,3-dicarboxylic acid anhydride derivative (B).

Next, the thiophene-2,3-dicarboxylic acid anhydride derivative (B) and the amine derivative are reacted at 50 to 180 ° C. to synthesize the 2,3-thiophenedicarboxylic acid imide derivative (C).

(In the formula, Y is a hydrogen atom or a halogen atom.)
Furthermore, the 2,3-thiophenedicarboxylic imide derivative (C) is dimerized in an organic solvent at 50 to 150 ° C. in the presence of a palladium catalyst to synthesize a compound represented by the general formula (1).

(In the formula, Z represents a hydrogen atom, a halogen atom, or a general formula.

(In the formula, R is a hydrogen atom or an alkyl group, and when R is an alkyl group, the two Rs may form a ring together.)
Or a group represented by the general formula

(In the formula, R ′ is an alkyl group.)
It is group represented by these. )
Although it does not specifically limit as a palladium catalyst, Bis (acetonitrite) palladium (II) Dichloride, Bis (benzonitile) palladium (II) Dichloride, [1,1'-Bis (diphenylphosphino) palladium (II) -Tert-butylphosphine) palladium (0), Palladium (II) Acetate, Tetrakis (triphenylphosphine) palladium (0), and the like.

  The organic solvent is not particularly limited, and examples thereof include benzene, toluene, xylene, chloronaphthalene, acetic acid, pyridine, methylpyridine, N, N-dimethylformamide, N, N-dimethylacetamide, carbon tetrachloride, chloroform, and dichloromethane. It is done.

  In addition, for example, the 2,3-thiophenedicarboxylic acid imide derivative (C) can be synthesized using the synthesis method described in Patent Document 2.

  In addition, for example, by dimerizing the 2,3-thiophenedicarboxylic imide derivative (C) in the presence of a palladium catalyst and silver fluoride in dimethyl sulfoxide, X is represented by the general formula (1) in which a single bond is present. (See J. Am Chem. Soc. 2006, 128, 10930-10933).

  Further, for example, by dimerizing the 2,3-thiophenedicarboxylic acid imide derivative (C) in the presence of a bisboronic acid derivative or a bisorganotin derivative or a palladium catalyst in a solvent such as toluene, xylene, or THF, X is obtained. A compound represented by the general formula (1) which is a substituted or unsubstituted arylene group can be synthesized (see Macromolecules 2008, 41, 6012-6018, J. Chem. Soc. Chem. Commun. 1979, 866). .

  Further, for example, by dimerizing the 2,3-thiophenedicarboxylic acid imide derivative (C) in the presence of diiodo derivative, palladium catalyst, potassium fluoride, silver nitrate in DMSO, X is a substituted or unsubstituted arylene group It is possible to synthesize a compound represented by the general formula (1) (see Journal of Physics: Conference Series, 2010, 232, 012010).

  Although it does not specifically limit as an alkyl group in General formula (1), A methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, a heptyl group, 2-heptyl group, an undecanyl group etc. are mentioned.

  Although it does not specifically limit as an aromatic hydrocarbon group in General formula (1), Monovalent group derived from aromatic rings, such as benzene, biphenyl, naphthalene, anthracene, fluorene, pyrene, pyridine, quinoline, thiophene, furan, oxazole , Monovalent groups derived from aromatic heterocycles such as oxadiazole and carbazole.

  Although it does not specifically limit as a halogen atom in General formula (1), A fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned.

  The arylene group in the general formula (1) is not particularly limited, but is a divalent group derived from an aromatic ring such as benzene, biphenyl, naphthalene, anthracene, fluorene, pyrene, pyridine, quinoline, thiophene, furan, oxazole, oxadi And divalent groups derived from aromatic heterocycles such as azole and carbazole.

  As the substituent in the general formula (1), the above alkyl group, methoxy group, ethoxy group, propoxy group, butoxy group and other alkoxy groups, fluoroalkyl group, the above halogen atom, dialkylamino group, diphenylamino group, nitro Groups, the above-mentioned aromatic hydrocarbon groups, monovalent groups derived from aromatic heterocycles such as pyrrolidine, piperidine, piperazine and the like.

  Although it does not specifically limit as a compound represented by General formula (1), The compound etc. which are represented by Chemical formula (1-1)-(1-28) are mentioned.

The hole transport material preferably includes a low molecular hole transport material.

  Although it does not specifically limit as a low molecular hole transport material, An oxazole derivative, an imidazole derivative, a triphenylamine derivative etc. are mentioned, You may use together 2 or more types. Among these, compounds represented by the general formulas (2) to (5) are preferable.

(Wherein X is a single bond or vinylene group, R ₁₀₂ is a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Ar ₁₀₁ is substituted or unsubstituted. A substituted aromatic hydrocarbon group, R ₁₀₁ is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and R ₁₀₁ is a substituted or unsubstituted alkyl group or substituted Alternatively, when it is an unsubstituted aromatic hydrocarbon group, Ar ₁₀₁ and R ₁₀₁ may form a ring together, and A is represented by the general formula

Or general formula

Wherein R ₁₀₃ and R ₁₀₄ are a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or a general formula

(Wherein R ₁₀₅ and R ₁₀₆ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R ₁₀₅ and R ₁₀₆ jointly form a ring; May be good.)
It is group represented by these. )
A group represented by the formula: 9-anthryl group or substituted or unsubstituted carbazolyl group, q ₁ and q ₂ are each an integer of 1 to 3, and q ₁ is 2 or 3, a plurality of R ₁₀₃ May be the same or different, and when q ₂ is 2 or 3, the plurality of R ₁₀₄ may be the same or different. )

Wherein R ₁₀₈ , R ₁₀₉ and R ₁₁₀ are each independently a hydrogen atom, amino group, alkoxy group, thioalkoxy group, aryloxy group, methylenedioxy group, substituted or unsubstituted alkyl group, halogen atom Or a substituted or unsubstituted aromatic hydrocarbon group, R ₁₀₇ is a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and r, s, t and u are each independently When it is an integer of 1 or more and 4 or less and s is an integer of 2 or more and 4 or less, the plurality of R ₁₀₇ may be the same or different, and r is an integer of 2 or more and 4 or less. in some cases, multiple by R ₁₀₈ may be the same or different, when u is 2 to 4 integer, a plurality of R ₁₀₉ independently represent, it may be the same, different May have, when t is 2 to 4 integer multiple by R ₁₁₀ may be the same or different.)

(Wherein Y is a single bond or vinylene group, R ₁₁₁ is a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Ar ₁₀₂ is substituted or unsubstituted. A substituted aromatic hydrocarbon group, R ₁₁₂ is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and R ₁₁₂ is a substituted or unsubstituted alkyl group or substituted Alternatively, when it is an unsubstituted aromatic hydrocarbon group, Ar ₁₀₂ and R ₁₁₂ may form a ring together, and R ₁₁₃ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic carbon group. A hydrogen group, Ar ₁₀₃ is represented by the general formula

Or general formula

(Wherein R ₁₁₄ and R ₁₁₅ are a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, q ₃ and q ₄ are integers of 1 or more and 3 or less, and q ₃ is 2 or 3, The plurality of R ₁₁₄ may be the same or different, and when q ₄ is 2 or 3, the plurality of R ₁₁₅ may be the same or different. )
It is group represented by these. )

(In the formula, Z is a single bond or a vinylene group, R ₁₁₆ is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar ₁₀₄ is a substituted or unsubstituted group. A substituted divalent aromatic hydrocarbon group, R ₁₁₇ represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Z represents a general formula

Or general formula

Wherein R ₁₁₈ and R ₁₁₉ are a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a general formula

(Wherein R ₁₂₀ and R ₁₂₁ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and may form a ring together)
Q ₅ and q ₆ are integers of 1 or more and 3 or less, and when q ₅ is 2 or 3, a plurality of R ₁₁₈ may be the same or different. In addition, when q ₆ is 2 or 3, the plurality of R ₁₁₉ may be the same or different. )
Or a 9-anthryl group or a substituted or unsubstituted carbazolyl group. )
The electron transport material may further contain a low-molecular electron transport material other than the compound represented by the general formula (1).

  Although it does not specifically limit as a low molecular electron transport material other than the compound represented by General formula (1), Chloranil, bromanyl, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone 2,4,5,7-tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, 2,6,8-trinitro-indeno-4H-indeno [1,2-b] thiophen-4-one, 1,3,7-trinitrodibenzothiophene-5,5-dioxide and the like may be mentioned, and two or more kinds may be used in combination. Among these, compounds represented by the general formulas (6) to (9) are preferable.

(Wherein R ₁₂₂ and R ₁₂₃ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.)

Wherein R ₁₂₄ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R ₁₂₅ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted Or an unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group.)

(Wherein R ₁₂₇ and R ₁₂₈ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.)

(Wherein R ₁₂₉ and R ₁₃₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.)
The charge transport material may further contain a polymer charge transport material.

  The polymer charge transport material is not particularly limited, but poly (N-vinylcarbazole) and its derivatives, poly (γ-carbazolylethyl glutamate) and its derivatives, pyrene-formaldehyde condensate and its derivatives, polyvinylpyrene, A polyvinyl phenanthrene etc. are mentioned, You may use 2 or more types together. Among these, a polycarbonate having a triarylamine structure in the main chain and / or side chain is preferable.

  The binder resin is not particularly limited, but polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer. , Polyvinyl acetate, polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin, phenol Examples thereof include resins and alkyd resins.

  The thickness of the charge transport layer (37) is preferably 25 μm or less from the viewpoint of resolution and responsiveness. The thickness of the charge transport layer (37) is usually 5 μm or more.

  The charge transport layer (37) is formed by applying a coating solution in which a composition containing a binder resin and an electron transport material is dissolved or dispersed in an organic solvent on the charge generation layer (35) and then drying. be able to.

  Examples of the organic solvent include, but are not limited to, tetrahydrofuran, dioxane, toluene, dichloromethane, monochlorobenzene, dichloroethane, cyclohexanone, methyl ethyl ketone, and acetone, and two or more kinds may be used in combination.

  The disperser used for dissolving or dispersing the composition in an organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  The method for applying the coating liquid is not particularly limited, and examples thereof include a dipping method, a spray coating method, a beat coating method, a nozzle coating method, a spinner coating method, and a ring coating method.

The conductive support (31) is not particularly limited as long as it has a volume resistivity of 1 × 10 ¹⁰ Ω · cm or less, but aluminum, nickel, chromium, nichrome, copper, gold, silver Metals such as platinum, metal oxides such as tin oxide and indium oxide are deposited or sputtered to form film or cylindrical plastic, paper coated, aluminum, aluminum alloy, nickel, stainless steel, etc. After extruding the plates and making them into raw pipes by a method such as drawing and drawing, pipes that have been subjected to surface treatment such as cutting, superfinishing, and polishing can be used.

  Further, an endless nickel belt and an endless stainless steel belt disclosed in JP-A-52-36016 can also be used as the conductive support (31).

  Further, a substrate in which a conductive layer in which conductive powder is dispersed in a binder resin is formed on a support can also be used as the conductive support (31).

The conductive powder is not particularly limited, but carbon black, acetylene black,
Examples thereof include powders of metals such as aluminum, nickel, iron, nichrome, copper, zinc, and silver, and powders of metal oxides such as conductive tin oxide and ITO.

  The binder resin is not particularly limited, but polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer. , Polyvinyl acetate, polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin, phenol Examples thereof include resins and alkyd resins.

  The conductive layer can be formed by applying a coating solution in which conductive powder and a binder resin are dissolved or dispersed in an organic solvent on a support and then drying.

  Although it does not specifically limit as an organic solvent, Tetrahydrofuran, a dichloromethane, methyl ethyl ketone, toluene etc. are mentioned, You may use 2 or more types together.

  The disperser used for dissolving or dispersing the composition in an organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  Moreover, what has a conductive layer formed of a heat shrinkable tube in which conductive powder is dispersed in a resin on a cylindrical substrate can also be used as the conductive support (31).

  The resin is not particularly limited, and examples thereof include polyvinyl chloride, polypropylene, polyester, polystyrene, polyvinylidene chloride, polyethylene, chlorinated rubber, and Teflon (registered trademark).

  The charge generation layer (35) includes a charge generation material.

  Although it does not specifically limit as a charge generation substance, C eye pigment blue 25 (color index CI 21180), C eye pigment red 41 (CI 21200), C eye acid red 52 (CI 45100), C eye basic red 3 (CI 45210), carbazole An azo pigment having a skeleton (see JP-A-53-95033), an azo pigment having a distyrylbenzene skeleton (see JP-A-53-133445), and an azo pigment having a triphenylamine skeleton (JP-A-53) No. -132347), an azo pigment having a dibenzothiophene skeleton (see JP 54-21728), an azo pigment having an oxadiazole skeleton (see JP 54-12742), and a fluorenone skeleton Azo pigment (special No. 54-22834), azo pigments having a bis-stilbene skeleton (see JP 54-17733), azo pigments having a distyryloxadiazole skeleton (see JP 54-2129), An azo pigment having a distyrylcarbazole skeleton (see JP 54-14967 A), an azo pigment such as an azo pigment having a benzanthrone skeleton, CI Pigment Blue 16 (CI 74100), Y-type oxotitanium phthalocyanine (JP 64-17066), A (β) -type oxotitanium phthalocyanine, B (α) -type oxotitanium phthalocyanine, I-type oxotitanium phthalocyanine (see JP-A-11-21466), II-type chlorogallium phthalocyanine (Iijima et al.) , The 67th Annual Meeting of the Chemical Society of Japan, 1 B4,04 (1994)), V-type hydroxygallium phthalocyanine (Damon et al., The 67th Annual Meeting of the Chemical Society of Japan, 1B4,05 (1994)), X-type metal-free phthalocyanine (see US Pat. No. 3,816,118), etc. Pigments, indigo pigments such as C-Ibat Brown 5 (CI 73410), C-Ibat Die (CI 73030), perylene pigments such as Argo Scarlet B (manufactured by Bayer), and Insence Scarlet R (manufactured by Bayer) 2 or more may be used in combination.

  The charge generation layer (35) may further contain a binder resin.

  The binder resin is not particularly limited, but polyamide, polyurethane, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, polysulfone, polyacrylamide, polyvinyl benzal, polyester, Examples include phenoxy resin, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyphenylene oxide, polyamide, polyvinyl pyridine, cellulose resin, casein, polyvinyl alcohol, polyvinyl pyrrolidone and the like.

  The mass ratio of the binder resin to the charge generating substance is usually 0 to 5, and preferably 0.1 to 3.

The thickness of the charge generation layer (35) is usually 0.01 to 5 μm, and preferably 0.1 to 2 μm. The charge generation layer (35) is a composition containing a charge generation material in an organic solvent. It can be formed by applying a coating solution dissolved or dispersed in a conductive support (31) and then drying.

  Examples of the organic solvent include, but are not limited to, isopropanol, acetone, methyl ethyl ketone, cyclohexanone, tetrahydrofuran, dioxane, ethyl cellosolve, ethyl acetate, methyl acetate, dichloromethane, dichloroethane, monochlorobenzene, cyclohexane, toluene, xylene, ligroin and the like. Two or more kinds may be used in combination. Of these, ketone solvents, ester solvents, and ether solvents are preferable.

  The disperser used for dissolving or dispersing the charge generating substance in the organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  The method for applying the coating liquid is not particularly limited, and examples thereof include a dipping method, a spray coating method, a beat coating method, a nozzle coating method, a spinner coating method, and a ring coating method.

  An undercoat layer may be further formed between the conductive support (31) and the charge generation layer (35).

  The undercoat layer includes a binder resin.

  The binder resin is not particularly limited as long as it is a resin having high resistance to the organic solvent contained in the coating solution used when forming the charge generation layer (35), but polyvinyl alcohol, casein, sodium polyacrylate, etc. Examples include water-soluble resins, alcohol-soluble resins such as copolymer nylon and methoxymethylated nylon, curable resins such as polyurethane, melamine resins, phenol resins, alkyd-melamine resins, and epoxy resins.

  The undercoat layer may further include a metal oxide powder. Thereby, moire can be prevented and the residual potential can be reduced.

  Although it does not specifically limit as a metal oxide, A titanium oxide, a silica, an alumina, a zirconium oxide, a tin oxide, an indium oxide etc. are mentioned.

  The undercoat layer can be formed by applying a coating solution in which a composition containing a binder resin is dissolved or dispersed in an organic solvent on the conductive support (31) and then drying it.

  Although it does not specifically limit as an organic solvent, Tetrahydrofuran, a dioxane, a dichloroethane, a cyclohexane etc. are mentioned, You may use 2 or more types together.

  The disperser used for dissolving or dispersing the composition in an organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  A method for applying the coating solution is not particularly limited, and examples thereof include a dipping method, a spray coating method, a bead coating method, and a ring coating method.

  In addition, you may form an undercoat layer using a silane coupling agent, a titanium coupling agent, a chromium coupling agent, etc. instead of apply | coating a coating liquid.

  Moreover, when using the electroconductive support body (31) made from aluminum, you may form an undercoat layer by anodizing instead of apply | coating a coating liquid.

Further, an undercoat layer containing an organic substance such as polyparaxylylene (parylene), an inorganic substance such as SiO ₂ , SnO ₂ , TiO ₂ , ITO, or CeO ₂ by using a vacuum thin film manufacturing method instead of applying a coating solution. May be formed.

  The thickness of the undercoat layer is usually 0 to 5 μm.

  FIG. 2 shows another example of the layer structure of the photoreceptor.

  In the photoreceptor (10), a photosensitive layer (33) is formed on a conductive support (31). At this time, the photosensitive layer includes a binder resin, a charge generation material, and an electron transport material.

  The charge generation material is the same as the charge generation material contained in the charge generation layer (35).

  The electron transport material is the same as the electron transport material contained in the charge transport layer (37).

  It is preferable that the photosensitive layer (33) further contains a hole transport material, like the charge transport layer (37).

  As the binder resin, the binder resin contained in the charge transport layer (37) may be used alone or in combination with the binder resin contained in the charge generation layer (35).

  The mass ratio of the charge generating material to the binder resin is usually 0.05 to 0.4.

  The mass ratio of the charge transport material to the binder resin is usually 0.05 to 1.9, and preferably 0.5 to 1.5.

  The thickness of the photosensitive layer (33) is usually 5 to 25 μm.

  The photosensitive layer (33) is coated with a coating solution prepared by dissolving or dispersing a composition containing a binder resin, an electron transport material and a charge generation material in an organic solvent, and then dried. Can be formed.

  Although it does not specifically limit as an organic solvent, Tetrahydrofuran, a dioxane, a dichloroethane, a cyclohexane etc. are mentioned, You may use 2 or more types together.

  The disperser used for dissolving or dispersing the composition in an organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  A method for applying the coating solution is not particularly limited, and examples thereof include a dipping method, a spray coating method, a bead coating method, and a ring coating method.

  FIG. 3 shows another example of the layer structure of the photoreceptor.

  The photoconductor (10) has the same configuration as the photoconductor of FIG. 1 except that a protective layer (39) is further formed on the charge transport layer (37).

  The protective layer (39) contains a binder resin.

  The binder resin is not particularly limited, but ABS resin, ACS resin, olefin-vinyl monomer copolymer, chlorinated polyether, aryl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallylsulfone, Polybutylene, polybutylene terephthalate, polycarbonate, polyethersulfone, polyethylene, polyethylene terephthalate, polyimide, acrylic resin, polymethylbenten, polypropylene, polyphenylene oxide, polysulfone, polystyrene, polyarylate, AS resin, butadiene-styrene copolymer, polyurethane, Examples thereof include resins such as polyvinyl chloride, polyvinylidene chloride and epoxy resin. Of these, polycarbonate and polyarylate are preferred from the viewpoint of filler dispersibility, residual potential, and coating film defects.

  The protective layer (39) may further contain a filler. Thereby, abrasion resistance can be improved.

  Similarly to the charge transport layer (37), the protective layer (39) may further contain a charge transport material. Thereby, the residual potential can be reduced and the image quality can be improved.

  The protective layer (39) can be formed by applying a coating solution in which a composition containing a binder resin is dissolved or dispersed in an organic solvent on the charge transport layer (37) and then drying.

  Examples of the organic solvent include, but are not limited to, tetrahydrofuran, dioxane, toluene, dichloromethane, monochlorobenzene, dichloroethane, cyclohexanone, methyl ethyl ketone, and acetone, and two or more kinds may be used in combination.

  The disperser used for dissolving or dispersing the composition in an organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  The method for applying the coating liquid is not particularly limited, and examples thereof include a dipping method, a spray coating method, a beat coating method, a nozzle coating method, a spinner coating method, and a ring coating method.

  An intermediate layer may be further formed between the charge transport layer (37) and the protective layer (39).

  The intermediate layer includes a binder resin.

  Although it does not specifically limit as binder resin, Polyamide, alcohol-soluble nylon, water-soluble polyvinyl butyral, polyvinyl butyral, polyvinyl alcohol, etc. are mentioned.

  The intermediate layer can be formed by applying a coating solution in which a composition containing a binder resin is dissolved or dispersed in an organic solvent on the charge transport layer (37) and then drying.

  Although it does not specifically limit as an organic solvent, Tetrahydrofuran, a dioxane, a dichloroethane, a cyclohexane etc. are mentioned, You may use 2 or more types together.

  The disperser used for dissolving or dispersing the composition in an organic solvent is not particularly limited, and examples thereof include a ball mill, an attritor, a sand mill, and an ultrasonic disperser.

  A method for applying the coating solution is not particularly limited, and examples thereof include a dipping method, a spray coating method, a bead coating method, and a ring coating method.

  As a method for forming the intermediate layer, a generally used coating method as described above is employed.

  The thickness of the intermediate layer is usually 0.05 to 2 μm.

  In the photoreceptor of FIG. 2, a protective layer (39) may be further formed on the photosensitive layer (33).

  Each layer such as a charge generation layer (35), a charge transport layer (37), a photosensitive layer (33), a protective layer (39), an undercoat layer, and an intermediate layer is made of an antioxidant, a plasticizer, a lubricant, an ultraviolet absorber, It may further contain a leveling agent and the like. Thereby, a decrease in sensitivity and an increase in residual potential can be suppressed.

  FIG. 4 shows an example of the image forming apparatus.

  The photoconductor (10) rotates in the direction of the arrow in the figure, and around the photoconductor (10), a charging member (11), an image exposure member (12), a developing member (13), and a transfer member (16). ), A cleaning member (17), a charge removal member (18), and the like are disposed.

  The cleaning member (17) and the charge removal member (18) may be omitted.

  The operation of the image forming apparatus is basically as follows. The surface of the photoreceptor (10) is charged almost uniformly by the charging member (11). Subsequently, image light is written in response to the input signal by the image exposure member (12) to form an electrostatic latent image. Next, the electrostatic latent image is developed by the developing member (13), and a toner image is formed on the surface of the photoreceptor (10). The toner image formed on the surface of the photoreceptor (10) is transferred by the transfer member (16) to the transfer paper (15) sent to the transfer site by the transport roller (14). The toner image transferred to the transfer paper (15) is fixed on the transfer paper (15) by a fixing device (not shown). Part of the toner that has not been transferred to the transfer paper (15) is removed by the cleaning member (17). Subsequently, the charge remaining on the photoreceptor (10) is removed by the charge eliminating member (18), and the process proceeds to the next cycle.

  The photoreceptor (10) has a drum shape, but may have a sheet shape or an endless belt shape.

  As the charging member (11) and the transfer member (16), a roller-shaped charging member, a brush-shaped charging member, or the like is used in addition to a corotron, a scorotron, a solid state charger (solid state charger).

  On the other hand, as a light source for the image exposure member (12) and the charge removal member (18), fluorescent lamp, tungsten lamp, halogen lamp, mercury lamp, sodium lamp, light emitting diode (LED), semiconductor laser (LD), electroluminescence (EL) Etc. can be used. Among these, a semiconductor laser (LD) and a light emitting diode (LED) are preferable.

  In order to irradiate the photoconductor (10) only with light in a desired wavelength range, filters such as a sharp cut filter, a band pass filter, a near infrared cut filter, a dichroic filter, an interference filter, and a color temperature conversion filter are used. May be.

  Further, a transfer process using light irradiation, a static elimination process, a cleaning process, a pre-exposure process, and the like may be provided to irradiate the photoconductor (10) with light from a light source.

  Further, the charge remaining on the photoconductor (10) may be removed by applying a reverse bias in the charging step or the cleaning step.

  When the photoconductor (10) is positively (or negatively) charged and image exposure is performed, a positive (or negative) electrostatic latent image is formed on the surface of the photoconductor (10). When the toner image formed on the surface of the photoreceptor (10) is developed with negative (or positive) toner, a positive image is formed, and when developed with positive (or negative) toner, a negative image is formed. .

  As the cleaning member (17), a cleaning blade, a cleaning brush, or the like is used, and two or more kinds may be used in combination.

  The photoreceptor (10) can be applied to a small-diameter photoreceptor. As an image forming apparatus in which a small-diameter photoconductor is used more effectively, a so-called tandem type image which includes a plurality of photoconductors corresponding to each developing unit corresponding to a plurality of colors of toner and performs parallel processing. Examples include a forming apparatus. A tandem image forming apparatus includes at least four color toners of yellow (C), magenta (M), cyan (C), and black (K), which are required for full-color printing, and a developing unit that holds them. And at least four photoconductors corresponding to these. This enables high-speed full color printing.

  FIG. 5 shows a tandem full-color image forming apparatus as another example of the image forming apparatus.

  The photoconductors (10C (cyan)), (10M (magenta)), (10Y (yellow)), and (10K (black)) are in the form of a drum, and rotate in the direction of the arrow in the figure. Members (11C, 11M, 11Y, 11K), developing members (13C, 13M, 13Y, 13K), and cleaning members (17C, 17M, 17Y, 17K) are arranged.

  Laser light (12C) from an exposure member (not shown) from the back side of the photoreceptor (10) between the charging member (11C, 11M, 11Y, 11K) and the developing member (13C, 13M, 13Y, 13K). , 12M, 12Y, 12K), and electrostatic latent images are formed on the photoconductors (10C, 10M, 10Y, 10K).

  Then, four image forming units (20C, 20M, 20Y, 20K) centering on such photoconductors (10C, 10M, 10Y, 10K) are arranged along a transfer conveyance belt (19) which is a transfer material conveyance unit. Are juxtaposed.

  The transfer conveyance belt (19) is disposed between the developing member (13C, 13M, 13Y, 13K) of each image forming unit (20C, 20M, 20Y, 20K) and the cleaning member (17C, 17M, 17Y, 17K). It is in contact with the photoreceptor (10C, 10M, 10Y, 10K). Transfer members (16C, 16M, 16Y, 16K) for applying a transfer bias are arranged on the side opposite to the side in contact with the photoreceptors (10C, 10M, 10Y, 10K) of the transfer conveyance belt (19). Each image forming element (20C, 20M, 20Y, 20K) has the same configuration except that the color of the toner of the developing member (13C, 13M, 13Y, 13K) is different.

  The image forming operation is performed as follows. First, in each of the image forming units (20C, 20M, 20Y, and 20K), the photosensitive member (10C, 10M, 10Y, and 10K) is rotated along with the photosensitive member (10C, 10M, 10Y, and 10K). (11C, 11M, 11Y, 11K), and then photoconductors (10C, 10M, 10Y, 10K) by laser light (12C, 12M, 12Y, 12K) irradiated from an exposure member (not shown). In addition, an electrostatic latent image corresponding to each color image is formed. Next, the electrostatic latent image is developed by a developing member (13C, 13M, 13Y, 13K) to form a toner image. The developing members (13C, 13M, 13Y, 13K) are developed with toner of each color, and the toner images of each color formed on the four photoconductors (10C, 10M, 10Y, 10K) are transferred to the transfer conveyance belt (19). It is transferred to the top and superimposed.

  The transfer paper (15) is fed out of the tray by the paper feed roller (21), temporarily stopped by the pair of registration rollers (22), and the timing and timing of image formation on the photoconductor (10C, 10M, 10Y, 10K). Together, it is sent to the transfer member (23). The toner images transferred and superimposed on the transfer conveyance belt (19) are transferred onto the transfer paper (15) by an electric field formed by the potential difference between the transfer bias applied to the transfer member (23) and the transfer belt (19). Transcribed above. The toner image transferred onto the transfer paper is conveyed to a fixing member (24), fixed, and then discharged to a paper discharge section (not shown). In addition, the toner remaining on each photoconductor (10C, 10M, 10Y, 10K) without being transferred by the transfer unit is removed from the cleaning member (17C, 17M, 17Y, 17K).

  In FIG. 5, the transfer conveyance belt (19) is used as the intermediate transfer member, but intermediate transfer members having various shapes and materials such as a drum shape and a belt shape can be used.

  Also, in FIG. 5, the image forming units (20C, 20M, 20Y, 20K) are C (cyan), M (magenta), Y (from the upstream side to the downstream side in the transport direction of the transfer paper (15). The color is arranged in the order of yellow) and K (black), but is not particularly limited.

  Furthermore, when an image of only K (black) is formed, a mechanism that stops the image forming units (20C, 20M, 20Y) other than K (black) can be provided.

  The image forming apparatus is not particularly limited, and examples thereof include a copying apparatus, a facsimile machine, and a printer.

  The image forming units (20C, 20M, 20Y, 20K) may be fixedly incorporated in the image forming apparatus, but may be detachably incorporated in the image forming apparatus in the form of a process cartridge.

  FIG. 6 shows an example of the process cartridge.

  The process cartridge contains a photoreceptor (10), and includes a charging member (11), an image exposure member (12), a developing member (13), a transfer member (16), and a cleaning member (17).

  In addition, the compound represented by General formula (1) is applicable also to the material for organic electronics used for an organic transistor, organic EL, an organic solar cell, etc.

  Hereinafter, the present invention will be described in detail with reference to examples. In addition, a part means a mass part.

(Synthesis of 2,3-thiophene dicarboxylic acid anhydride)
After mixing 15 g (87.2 mmol) of 2,3-thiophenedicarboxylic acid and 300 mL of acetic anhydride, the mixture was refluxed in the atmosphere for 5 hours. Next, after distilling off the solvent under reduced pressure, the reaction crude product was recrystallized with toluene / n-hexane to obtain a chemical formula.

A colorless crystal of 2,3-thiophenedicarboxylic anhydride represented by The yield of 2,3-thiophenedicarboxylic anhydride was 11.1 g, the yield was 81.8%, and the melting point was 244.0-246.0 ° C. (decomp.).

  FIG. 7 shows an infrared transmission spectrum (KBr tablet method) of 2,3-thiophenedicarboxylic anhydride.

(Synthesis of N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide)
After mixing 3.3 g (21.4 mmol) of 2,3-thiophenedicarboxylic anhydride, 2.59 g (22.5 mmol) of 2-heptylamine and 150 mL of toluene, the mixture was refluxed with stirring for 2 hours in the atmosphere. Next, the reaction solution was concentrated under reduced pressure, and 100 mL of dioxane and 10 mL of thionyl chloride were added to the reaction crude product, followed by refluxing with stirring for 2 hours under an argon atmosphere. Further, after the reaction solution was concentrated under reduced pressure, the reaction crude product was purified by silica gel column chromatography (developing solvent: toluene) to obtain a colorless oily chemical formula.

N- (1-methylhexyl) -2,3-thiophenedicarboxylic acid imide represented by the formula: The yield of N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide was 4.55 g, and the yield was 84.7%.

  FIG. 8 shows an infrared transmission spectrum (KBr tablet method) of N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide.

(Synthesis of N- (3-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide)
(Synthesis of N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide)
After mixing 2.0 g (12.99 mmol) of 2,3-thiophenedicarboxylic anhydride, 2.2 g (13.64 mmol) of 3-trifluoromethylaniline and 150 mL of toluene, the mixture was refluxed with stirring for 2 hours in the atmosphere. did. Next, the reaction solution was concentrated under reduced pressure, and 100 mL of dioxane and 10 mL of thionyl chloride were added to the reaction crude product, followed by refluxing with stirring for 2 hours under an argon atmosphere. Furthermore, after concentrating the reaction solution under reduced pressure, the reaction crude product is purified by silica gel column chromatography (developing solvent: toluene) to obtain a light yellow powdery chemical formula.

N- (3-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide represented by the formula: The yield of N- (3-trifluoromethylphenyl) -2,3-thiophenedicarboxylic imide was 3.6 g, and the yield was 93.3%.

  FIG. 9 shows an infrared transmission spectrum (KBr tablet method) of N- (3-trifluoromethylphenyl) -2,3-thiophenedicarboxylic imide.

(Synthesis of N- (2-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide)
After mixing 2.0 g (12.99 mmol) of 2,3-thiophenedicarboxylic anhydride, 2.2 g (13.64 mmol) of 2-trifluoromethylaniline and 150 mL of toluene, the mixture was refluxed with stirring for 2 hours in the atmosphere. did. Next, the reaction solution was concentrated under reduced pressure, and 100 mL of dioxane and 10 mL of thionyl chloride were added to the reaction crude product, followed by refluxing with stirring for 2 hours under an argon atmosphere. Furthermore, after concentrating the reaction solution under reduced pressure, the reaction crude product is purified by silica gel column chromatography (developing solvent: toluene) to obtain a light yellow powdery chemical formula.

N- (2-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide represented by The yield of N- (2-trifluoromethylphenyl) -2,3-thiophenedicarboxylic imide was 3.2 g and the yield was 82.9%.

  FIG. 10 shows an infrared transmission spectrum (KBr tablet method) of N- (2-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide.

(Synthesis of 5-bromo-N-1-methylhexyl) -2,3-thiophenedicarboxylic acid imide)
400 mL of concentrated sulfuric acid and 200 mL of glacial acetic acid were added to 6.00 g (23.9 mmol) of N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide, and then cooled to 0 ° C. with ice water. Next, 6.00 g (33.7 mmol) of N-bromosuccinimide was added in 6 portions every hour, followed by stirring for 1 hour. Further, the reaction solution was gradually added dropwise to an aqueous sodium thiosulfate solution, and then the reaction mixture was extracted with ethyl acetate. Next, the organic layer was dried over magnesium sulfate and then filtered. Further, the filtrate was concentrated under reduced pressure, and then purified by silica gel column chromatography (developing solvent: toluene) to obtain a light yellow oily chemical formula.

5-bromo-N- (1-methylhexyl) -2,3-thiophenedicarboxylic acid imide represented by The yield of 5-bromo-N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide was 6.9 g, and the yield was 87.7%.
FIG. 11 shows an infrared transmission spectrum (KBr tablet method) of 5-bromo-N- (1-methylhexyl) -2,3-thiophenedicarboxylic acid imide.

(Synthesis of the compound represented by the chemical formula (1-9))
N- (1-methylhexyl) -2,3-thiophenedicarboxylic imide 2.0 g (7.96 mmol), PdCl ₂ (PhCN) ₂ 152 mg (0.39 mmol), silver fluoride 2.0 g (15.9 mmol) And 30 mL of DMSO were mixed, and then heated at 70 ° C. for 6 hours under an argon atmosphere. Next, the precipitate was filtered through celite, and the filtrate was extracted with toluene. Furthermore, the organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Next, the product was purified by silica gel column chromatography (developing solvent: toluene / dichloromethane = 7/3) and then recrystallized from ethanol to obtain a compound represented by the chemical formula (1-9). The compound represented by the chemical formula (1-9) had a yield of 780 mg, a yield of 39.2%, and a melting point of 127.0 to 128.0 ° C.

  FIG. 12 shows an infrared transmission spectrum (KBr tablet method) of the compound represented by the chemical formula (1-9).

(Synthesis of Compound Represented by Chemical Formula (1-15))
N- (3-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide 2.5 g (8.41 mmol), PdCl ₂ (PhCN) ₂ 160 mg (0.42 mmol), silver fluoride 2.1 g (16. 8 mmol) and 30 mL of DMSO were mixed and then heated at 70 ° C. for 6 hours under an argon atmosphere. Next, the precipitate was filtered through celite, and the filtrate was extracted with toluene. Furthermore, the organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Next, the product was purified by silica gel column chromatography (developing solvent: toluene / dichloromethane = 7/3) and then recrystallized from ethanol to obtain a compound represented by the chemical formula (1-15). The compound represented by the chemical formula (1-15) had a yield of 560 mg, a yield of 25.1%, and a melting point of 250 ° C. or higher.

  FIG. 13 shows an infrared transmission spectrum (KBr tablet method) of the compound represented by the chemical formula (1-15).

(Synthesis of the compound represented by the chemical formula (1-4))
N- (2-trifluoromethylphenyl) -2,3-thiophenedicarboxylic acid imide 2.5 g (8.41 mmol), PdCl ₂ (PhCN) ₂ 160 mg (0.42 mmol), silver fluoride 2.1 g (16. 8 mmol) and 30 mL of DMSO were mixed and then heated at 70 ° C. for 6 hours under an argon atmosphere. Next, the precipitate was filtered through celite, and the filtrate was extracted with toluene. Furthermore, the organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Next, the product was purified by silica gel column chromatography (developing solvent: toluene / dichloromethane = 7/3) and then recrystallized from ethanol to obtain a compound represented by the chemical formula (1-15). The compound represented by the chemical formula (1-15) had a yield of 1.0 g, a yield of 40.1%, and a melting point of 250 ° C. or higher.

  FIG. 14 shows an infrared transmission spectrum (KBr tablet method) of the compound represented by the chemical formula (1-4).

(Synthesis of the compound represented by the chemical formula (1-12))
2.1 g (6.4 mmol) of 5-bromo-N- (1-methylhexyl) -2,3-thiophenedicarboxylic acid imide, 0.51 g (3.05 mmol) of 1,4-phenylenediboronic acid, tetrakis (tri After mixing 173 mg (0.15 mmol) of phenylphosphine) palladium, 60 mL of toluene, and 30 mL of 20 mass% potassium carbonate aqueous solution, the mixture was refluxed for 7 hours under an argon atmosphere. Next, after allowing to cool at room temperature, the reaction crude product was extracted with ethyl acetate. Furthermore, the organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Next, after purification by silica gel column chromatography (developing solvent: toluene), recrystallization from ethanol / toluene gave a compound represented by the chemical formula (1-12). The compound represented by the chemical formula (1-12) had a yield of 1.0 g, a yield of 57.1%, and a melting point of 182.0-183.5 ° C.

  FIG. 15 shows an infrared transmission spectrum (KBr tablet method) of the compound represented by the chemical formula (1-12).

(Synthesis of the compound represented by the chemical formula (1-14))
N- (1-methylhexyl) -2,3-thiophenedicarboxylic acid imide 2.51 g (10.0 mmol), 1,4-diiodo-2,3,5,6-tetrafluorobenzene 1.93 g (4.80 mmol) ), 353 mg (0.48 mmol) of bis (triphenylphosphine) palladium dichloride, 1.16 g (20.0 mmol) of silver fluoride, and 25 mL of DMSO, and then heated and stirred at 100 ° C. under an argon atmosphere. Next, silver nitrate was divided into 5 times, 0.7 g was added every hour, and then heated and stirred for 1 hour. Furthermore, after allowing to cool at room temperature, the reaction crude product was filtered. Next, the filtrate was extracted with dichloromethane and water, and then the organic layer was dried over magnesium sulfate. Further, after filtration, the filtrate was concentrated under reduced pressure. Next, after refine | purifying with silica gel column chromatography (developing solvent: toluene), it recrystallized with ethanol / toluene, and the compound represented by Chemical formula (1-14) was obtained. The compound represented by the chemical formula (1-14) had a yield of 0.70 g, a yield of 10.8%, and a melting point of 170.5-171.5 ° C.

  FIG. 16 shows an infrared transmission spectrum (KBr tablet method) of the compound represented by the chemical formula (1-14).

[Example 1]
400 parts of titanium dioxide powder tie-bak CR-EL (manufactured by Ishihara Sangyo Co., Ltd.), 65 parts of melamine resin Super Becamine G821-60 (manufactured by Dainippon Ink), 120 parts of alkyd resin Beckolite M6401-50 (manufactured by Dainippon Ink) 400 parts of 2-butanone was mixed to obtain an undercoat layer coating solution.

  Chemical formula

12 parts of fluorenone-based bisazo pigment, 5 parts of polyvinyl butyral XYHL (manufactured by Union Carbide), 200 parts of 2-butanone and 400 parts of cyclohexanone were mixed to obtain a coating solution for a charge generation layer.

  10 parts of polycarbonate Z-polyca (manufactured by Teijin Chemicals Ltd.), 10 parts of the compound represented by the chemical formula (1-9) and 100 parts of tetrahydrofuran were mixed to obtain a coating solution for charge transport layer.

  A subbing layer coating solution, a charge generation layer coating solution and a charge transport layer coating solution are sequentially applied by an immersion method onto an aluminum cylinder having a diameter of 100 mm, and then dried to a thickness of 3.5 μm or less. A drawing layer, a charge generation layer having a thickness of 0.2 μm, and a charge transport layer having a thickness of 23 μm were formed to obtain a photoreceptor.

[Example 2]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-1) was used instead of the compound represented by the chemical formula (1-9).

[Example 3]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-4) was used instead of the compound represented by the chemical formula (1-9).

[Example 4]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-5) was used instead of the compound represented by the chemical formula (1-9).

[Example 5]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-7) was used instead of the compound represented by the chemical formula (1-9).

[Example 6]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-8) was used instead of the compound represented by the chemical formula (1-9).

[Example 7]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-12) was used instead of the compound represented by the chemical formula (1-9).

[Example 8]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-13) was used instead of the compound represented by the chemical formula (1-9).

[Example 9]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-15) was used instead of the compound represented by the chemical formula (1-9).

[Example 10]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-17) was used instead of the compound represented by the chemical formula (1-9).

[Example 11]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-21) was used instead of the compound represented by the chemical formula (1-9).

[Example 12]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-23) was used instead of the compound represented by the chemical formula (1-9).

[Example 13]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-24) was used instead of the compound represented by the chemical formula (1-9).

[Example 14]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-25) was used instead of the compound represented by the chemical formula (1-9).

[Example 15]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (1-27) was used instead of the compound represented by the chemical formula (1-9).

  A modified machine of imgio MF2200 (manufactured by Ricoh) in which the photoreceptors of Examples 1 to 15 are mounted on a process cartridge, the charging method is a positive corona discharge, and the image exposure light source is a semiconductor laser (LD) having a wavelength of 655 nm. After setting the dark part potential to 800 V, a repeated test equivalent to printing a total of 100,000 sheets was continuously performed. At that time, the bright part potential and image blur (dot resolution) after the initial and repeated tests were evaluated.

  Regarding image blurring, ten dot images having a pixel density of 600 dpi × 600 dpi and an image density of 5% were continuously printed out, and then the dot shape was observed with a stereomicroscope to evaluate the sharpness of the outline. It should be noted that the contour is clear and good, 5 and the blurring of the contour is very slightly observed, but the favorable contour is 4 and the blurring of the contour is very slightly observed, but substantially good In this case, 3 was determined, 2 was determined to be a problem depending on the type of image, and 2 was determined to be a problem.

  Table 1 shows the evaluation results of the photoreceptors of Examples 1 to 15.

From Table 1, it can be seen that the photoreceptors of Examples 1 to 15 can suppress the increase in the light potential and the occurrence of image blur even when 100,000 sheets are printed using positive corona discharge.

[Example 16]
10 parts of polycarbonate Z-polyca (manufactured by Teijin Chemicals Ltd.), 1 part of the compound represented by chemical formula (1-9), chemical formula

9 parts of a hole transport material represented by the formula and 100 parts of tetrahydrofuran were mixed to obtain a coating solution for charge transport layer.

  A photoconductor was obtained in the same manner as in Example 1 except that the obtained charge transport layer coating solution was used.

[Example 17]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-1) was used instead of the compound represented by the chemical formula (1-9).

[Example 18]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-4) was used instead of the compound represented by the chemical formula (1-9).

[Example 19]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-5) was used instead of the compound represented by the chemical formula (1-9).

[Example 20]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-7) was used instead of the compound represented by the chemical formula (1-9).

[Example 21]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-8) was used instead of the compound represented by the chemical formula (1-9).

[Example 22]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-12) was used instead of the compound represented by the chemical formula (1-9).

[Example 23]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-13) was used instead of the compound represented by the chemical formula (1-9).

[Example 24]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-15) was used instead of the compound represented by the chemical formula (1-9).

[Example 25]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-17) was used instead of the compound represented by the chemical formula (1-9).

[Example 26]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-21) was used instead of the compound represented by the chemical formula (1-9).

[Example 27]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-23) was used instead of the compound represented by the chemical formula (1-9).

[Example 28]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-24) was used instead of the compound represented by the chemical formula (1-9).

[Example 29]
A photoconductor was obtained in the same manner as in Example 16, except that the compound represented by the chemical formula (1-25) was used instead of the compound represented by the chemical formula (1-9).

[Example 30]
A photoconductor was obtained in the same manner as in Example 16 except that the compound represented by the chemical formula (1-27) was used instead of the compound represented by the chemical formula (1-9).

  The photoconductors of Examples 16 to 30 were evaluated in the same manner as the photoconductors of Examples 1 to 15 except that the charging method was changed to negative corona discharge (scorotron method) and the dark portion potential was set to -800V. did.

  Table 2 shows the evaluation results of the photoreceptors of Examples 16 to 30.

From Table 2, it can be seen that the photoreceptors of Examples 16 to 30 can suppress the increase in bright portion potential and the occurrence of image blur even when 100,000 sheets are printed using negative corona discharge.

[Example 31]
A photoconductor was obtained in the same manner as in Example 16 except that the addition amount of the hole transport material was changed to 7 parts.

[Example 32]
A photoconductor was obtained in the same manner as in Example 17 except that the addition amount of the hole transport material was changed to 7 parts.

[Example 33]
A photoconductor was obtained in the same manner as in Example 21 except that the addition amount of the hole transport material was changed to 7 parts.

[Example 34]
A photoconductor was obtained in the same manner as in Example 22 except that the addition amount of the hole transport material was changed to 7 parts.

[Example 35]
Instead of the hole transport material represented by the chemical formula (I), the chemical formula

A photoconductor was obtained in the same manner as in Example 31 except that the hole transport material represented by the formula (1) was used.

[Example 36]
A photoconductor was obtained in the same manner as in Example 32 except that the hole transport material represented by the chemical formula (II) was used instead of the hole transport material represented by the chemical formula (I).

[Example 37]
A photoconductor was obtained in the same manner as in Example 33 except that the hole transport material represented by the chemical formula (II) was used instead of the hole transport material represented by the chemical formula (I).

[Example 38]
A photoconductor was obtained in the same manner as in Example 34 except that the hole transport material represented by the chemical formula (II) was used instead of the hole transport material represented by the chemical formula (I).

[Example 39]
Instead of the hole transport material represented by the chemical formula (I), the chemical formula

A photoconductor was obtained in the same manner as in Example 31 except that the hole transport material represented by the formula (1) was used.

[Example 40]
A photoconductor was obtained in the same manner as in Example 32 except that the hole transport material represented by the chemical formula (III) was used instead of the hole transport material represented by the chemical formula (I).

[Example 41]
A photoconductor was obtained in the same manner as in Example 33 except that the hole transport material represented by the chemical formula (III) was used instead of the hole transport material represented by the chemical formula (I).

[Example 42]
A photoconductor was obtained in the same manner as in Example 34 except that the hole transport material represented by the chemical formula (III) was used instead of the hole transport material represented by the chemical formula (I).

[Example 43]
Instead of the hole transport material represented by the chemical formula (I), the chemical formula

A photoconductor was obtained in the same manner as in Example 31 except that the hole transport material represented by the formula (1) was used.

[Example 44]
A photoconductor was obtained in the same manner as in Example 32 except that the hole transport material represented by the chemical formula (IV) was used instead of the hole transport material represented by the chemical formula (I).

[Example 45]
A photoconductor was obtained in the same manner as in Example 33 except that the hole transport material represented by the chemical formula (IV) was used instead of the hole transport material represented by the chemical formula (I).

[Example 46]
A photoconductor was obtained in the same manner as in Example 34 except that the hole transport material represented by the chemical formula (IV) was used instead of the hole transport material represented by the chemical formula (I).

(Synthesis of oxotitanium phthalocyanine)
Oxotitanium phthalocyanine was synthesized in the same manner as in Synthesis Example 4 described in JP-A-2001-019871.

  After mixing 29.2 g of 1,3-diiminoisoindoline and 200 mL of sulfolane, 20.4 g of titanium tetrabutoxide was added dropwise under a nitrogen stream. Next, after heating up to 180 degreeC, it stirred for 5 hours, hold | maintaining between 170 degreeC-180 degreeC. Furthermore, after allowing to cool, the precipitate was filtered, and washed with chloroform until the powder turned blue. Next, it was washed several times with methanol, washed several times with hot water at 80 ° C., and then dried to obtain crude titanyl phthalocyanine. Further, the crude titanyl phthalocyanine was dissolved in 20 times the amount of concentrated sulfuric acid, and then added dropwise to 100 times the amount of ice water with stirring. Next, after the precipitated crystals were filtered, washing with water was repeated until the washing solution became neutral, and a titanyl phthalocyanine pigment wet cake was obtained. Further, 2 g of the wet cake was put into 20 g of carbon disulfide and stirred for 4 hours. Next, 100 g of methanol was added and stirred for 1 hour, then filtered and dried to obtain a crystalline powder of oxotitanium phthalocyanine.

  FIG. 17 shows an X-ray diffraction spectrum of oxotitanium phthalocyanine.

[Example 47]
8 parts of oxotitanium phthalocyanine, 5 parts of polyvinyl butyral BX-1 (manufactured by Sekisui Chemical Co., Ltd.) and 400 parts of 2-butanone were mixed to obtain a coating solution for charge generation layer.

  10 parts of polycarbonate Z-polyca (manufactured by Teijin Chemicals Ltd.), 1 part of a compound represented by chemical formula (1-9), 7 parts of a hole transporting material represented by chemical formula (I) and 70 parts of toluene are mixed together. A coating solution for a transport layer was obtained.

  A photoconductor was obtained in the same manner as in Example 16 except that the obtained charge generation layer coating solution and charge transport layer coating solution were used.

[Example 48]
A photoconductor was obtained in the same manner as in Example 47 except that the compound represented by the chemical formula (1-13) was used instead of the compound represented by the chemical formula (1-9).

  The photoreceptors of Examples 31 to 48 were evaluated in the same manner as the photoreceptors of Examples 16 to 30.

  Table 3 shows the evaluation results of the photoreceptors of Examples 31 to 48.

From Table 3, it can be seen that the photoreceptors of Examples 31 to 48 can suppress the increase in bright portion potential and the occurrence of image blur even when 100,000 sheets are printed using negative corona discharge.

[Example 49]
X-type metal-free phthalocyanine FastogenBlue 8120B (Dainippon Ink Chemical Co., Ltd.) 2 parts, chemical formula

20 parts of an electron transport material represented by the formula, 30 parts of a compound represented by the chemical formula (1-9), 50 parts of bisphenol Z-type polycarbonate Panlite TS-2050 (manufactured by Teijin Chemicals) and 500 parts of tetrahydrofuran are mixed and photosensitized. A layer coating solution was obtained.

  A photosensitive layer coating solution was applied on an aluminum cylinder having a diameter of 100 mm and then dried to form a photosensitive layer having a thickness of 30 μm to obtain a photoreceptor.

[Example 50]
A photoconductor was obtained in the same manner as in Example 49 except that the compound represented by the chemical formula (1-4) was used instead of the compound represented by the chemical formula (1-9).

[Example 51]
A photoconductor was obtained in the same manner as in Example 49 except that the compound represented by the chemical formula (1-12) was used instead of the compound represented by the chemical formula (1-9).

[Example 52]
A photoconductor was obtained in the same manner as in Example 49 except that the compound represented by the chemical formula (1-13) was used instead of the compound represented by the chemical formula (1-9).

[Example 53]
A photoconductor was obtained in the same manner as in Example 49 except that an aluminum cylinder having a diameter of 30 mm was used.

[Example 54]
A photoconductor was obtained in the same manner as in Example 53 except that the compound represented by the chemical formula (1-4) was used instead of the compound represented by the chemical formula (1-9).

[Example 55]
A photoconductor was obtained in the same manner as in Example 53 except that the compound represented by the chemical formula (1-12) was used instead of the compound represented by the chemical formula (1-9).

[Example 56]
A photoconductor was obtained in the same manner as in Example 53 except that the compound represented by the chemical formula (1-13) was used instead of the compound represented by the chemical formula (1-9).

[Example 57]
10 parts of bisphenol A polycarbonate Panlite C-1400 (manufactured by Teijin Chemicals Ltd.), 10 parts of the compound represented by the chemical formula (1-9) and 100 parts of toluene were mixed to obtain a coating solution for charge transport layer. .

  Mixing 0.5 parts of polyvinyl butyral XYHL (manufactured by UCC), 2 parts of X-type metal-free phthalocyanine FastogenBlue 8120B (manufactured by Dainippon Ink & Chemicals), 200 parts of cyclohexanone and 80 parts of methyl ethyl ketone to obtain a coating solution for charge generation layer It was.

  A coating solution for a charge transport layer and a coating solution for a charge generation layer are sequentially applied onto an aluminum cylinder having a diameter of 100 mm, and then dried to obtain a charge transport layer having a thickness of 20 μm and a charge having a thickness of 0.1 μm. A generation layer was formed to obtain a photoreceptor.

[Example 58]
A photoconductor was obtained in the same manner as in Example 57 except that the compound represented by the chemical formula (1-4) was used instead of the compound represented by the chemical formula (1-9).

[Example 59]
A photoconductor was obtained in the same manner as in Example 57 except that the compound represented by the chemical formula (1-12) was used instead of the compound represented by the chemical formula (1-9).

[Example 60]
A photoconductor was obtained in the same manner as in Example 57 except that the compound represented by the chemical formula (1-13) was used instead of the compound represented by the chemical formula (1-9).

  The dark part potential was set to 700 V using a remodeling machine of imgio Neo 752 (manufactured by Ricoh) in which the charging method was positive corona discharge (scorotron method) and the image exposure light source was remodeled to a semiconductor laser (LD) having a wavelength of 780 nm. Except for the above, the photoreceptors of Examples 49 to 60 were evaluated in the same manner as the photoreceptors of Examples 1 to 15.

  Table 4 shows the evaluation results of the photoreceptors of Examples 49-60.

From Table 4, it can be seen that the photoreceptors of Examples 49 to 60 can suppress the increase in bright portion potential and the occurrence of image blur even when 100,000 sheets are printed using positive corona discharge.

[Example 61]
10 parts of polycarbonate Z-polyca (manufactured by Teijin Chemicals), 1 part of a compound represented by chemical formula (1-9), 9 parts of an electron transport material represented by chemical formula (6-1) and 100 parts of tetrahydrofuran were mixed, A coating solution for a charge transport layer was obtained.

  A photoconductor was obtained in the same manner as in Example 47 except that the obtained charge transport layer coating solution was used.

[Example 62]
Instead of the electron transport material represented by the chemical formula (6-1), the chemical formula

A photoconductor was obtained in the same manner as in Example 61 except that the electron transport material represented by the formula (1) was used.

[Example 63]
Instead of the electron transport material represented by the chemical formula (6-1), the chemical formula

A photoconductor was obtained in the same manner as in Example 61 except that the electron transport material represented by the formula (1) was used.

[Example 64]
Instead of the electron transport material represented by the chemical formula (6-1), the chemical formula

A photoconductor was obtained in the same manner as in Example 61 except that the electron transport material represented by the formula (1) was used.

  The photoconductors of Examples 61 to 64 were evaluated in the same manner as the photoconductors of Examples 16 to 30, except that the charging method was changed to positive corona discharge (scorotron method) and the dark portion potential was set to 800V. .

  Table 5 shows the evaluation results of the photoreceptors of Examples 61 to 64.

From Table 5, it can be seen that the photoreceptors of Examples 61 to 64 can suppress the increase in bright portion potential and the occurrence of image blur even when 100,000 sheets are printed using positive corona discharge.

[Comparative Example 1]
A photoconductor was obtained in the same manner as in Example 1 except that the compound represented by the chemical formula (6-1) was used instead of the compound represented by the chemical formula (1-9).

[Comparative Example 2]
A photoconductor was obtained in the same manner as in Example 16 except that the compound represented by the chemical formula (1-9) was not added and the weight of the hole transport material represented by the chemical formula (I) was changed to 10 parts. It was.

[Comparative Example 3]
Instead of the compound represented by the chemical formula (1-9), the chemical formula

A photoconductor was obtained in the same manner as in Example 35 except that the hole transport material represented by the formula (see JP 2000-231204 A) was used.

[Comparative Example 4]
Instead of the compound represented by the chemical formula (1-9), the chemical formula

A photoconductor was obtained in the same manner as in Example 47 except that the hindered amine antioxidant represented by

[Comparative Example 5]
Instead of 20 parts of the compound represented by the chemical formula (1-9), 18 parts of the electron transport material represented by the chemical formula (7-1) and the chemical formula

A photoconductor was obtained in the same manner as in Example 49 except that 2 parts of the electron transport material represented by the formula:

[Comparative Example 6]
A photoconductor was obtained in the same manner as in Example 49 except that the electron transport material represented by the chemical formula (8-1) was used instead of the compound represented by the chemical formula (1-9).

[Comparative Example 7]
Instead of 10 parts of the compound represented by the chemical formula (1-9), 9 parts of the electron transport material represented by the chemical formula (7-1) and 1 part of the electron transport material represented by the chemical formula (6-2) were used. A photoconductor was obtained in the same manner as in Example 57 except that.

(Synthesis of N- (1-methylhexyl) -3,4-thiophenedicarboxylic acid imide)
J. et al. Am. Chem. In accordance with the method described in Soc, 2010, 132, 5330-5331, N- (1-methylhexyl) -3,4-thiophenedicarboxylic imide was synthesized.

  After mixing 2.5 g (14.5 mmol) of 3,4-thiophenedicarboxylic acid and 70 mL of acetic anhydride, the mixture was refluxed in the atmosphere for 2 hours. Next, after cooling to room temperature, the solvent was distilled off to obtain 2.1 g of a crude reaction product.

  After mixing 1.5 g (9.7 mmol) of the crude reaction product, 1.18 g (10.2 mmol) of 2-heptylamine and 50 mL of toluene, the mixture was refluxed with stirring for 1 hour in the atmosphere. Next, the reaction solution was concentrated under reduced pressure, and 100 mL of dioxane and 10 mL of thionyl chloride were added to the reaction crude product, followed by refluxing with stirring for 2 hours under an argon atmosphere. Further, after the reaction solution was concentrated under reduced pressure, the reaction crude product was purified by silica gel column chromatography (developing solvent: toluene). Next, it is recrystallized from methanol to give a chemical formula of colorless powder

N- (1-methylhexyl) -3,4-thiophenedicarboxylic acid imide represented by the formula: The yield of N- (1-methylhexyl) -3,4-thiophenedicarboxylic imide was 1.5 g, and the yield was 61.6%.

[Comparative Example 8]
A photoconductor was obtained in the same manner as in Example 1 except that N- (1-methylhexyl) -3,4-thiophenedicarboxylic imide was used instead of the compound represented by the chemical formula (1-9). It was.

  The photoconductors of Comparative Examples 1 to 8 were evaluated in the same manner as the photoconductors of Examples 1, 16, 35, 47, 49, 49, 57, and 1, respectively.

  Table 6 shows the evaluation results of the photoreceptors of Comparative Examples 1-8.

From Table 6, since the photoreceptors of Comparative Examples 1-4, 7, and 8 do not contain the compound represented by the general formula (1), the image blur may occur when printing 100,000 sheets. Recognize.

  Further, since the photosensitive members of Comparative Examples 5 and 6 do not contain the compound represented by the general formula (1), image blur occurs when 100,000 sheets are printed.

  Next, the photoconductors of Examples 1, 17, 33, 37, 48, 49, 59, and Comparative Example 2 were left in a desiccator in which the concentration of nitrogen oxide (NOx) was adjusted to 50 ppm for 4 days. Image quality was evaluated by observing the images formed before and after with a lens such as a magnifying glass. The conditions for forming an image are the same as described above, and the image quality was determined based on the criteria shown in Table 7.

Table 8 shows the evaluation results of the photoconductors of Examples 1, 17, 33, 37, 48, 49, 59 and Comparative Example 2.

From Table 8, it can be seen that the photoconductors of Examples 1, 17, 33, 37, 48, 49, and 59 are excellent in image quality after being left.

  On the other hand, the image quality of the photoconductor of Comparative Example 2 is deteriorated after being left.

DESCRIPTION OF SYMBOLS 10 Photoconductor 31 Conductive support 33 Photosensitive layer 35 Charge generation layer 37 Charge transport layer 39 Protective layer

WO2005 / 092901 JP-A-4-234393

Claims (12)

A photosensitive layer containing a charge generation material and an electron transport material is formed on the conductive support,
The electron transport material has the general formula
Wherein R ₁ and R ₄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R ₂ and R ₃ are each independently A hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, wherein R ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted group; R ₂ and R ₃ may together form a ring, and X is a single bond , a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group . is there.)
A photoreceptor comprising a compound represented by the formula:   The photoreceptor according to claim 1, wherein the photosensitive layer further contains a hole transport material. The hole transport material has a general formula
(Wherein X is a single bond or vinylene group, R ₁₀₂ is a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Ar ₁₀₁ is substituted or unsubstituted. A substituted aromatic hydrocarbon group, R ₁₀₁ is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and R ₁₀₁ is a substituted or unsubstituted alkyl group or substituted Alternatively, when it is an unsubstituted aromatic hydrocarbon group, Ar ₁₀₁ and R ₁₀₁ may form a ring together, and A is represented by the general formula
Or general formula
Wherein R ₁₀₃ and R ₁₀₄ are a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or a general formula
(Wherein R ₁₀₅ and R ₁₀₆ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R ₁₀₅ and R ₁₀₆ jointly form a ring; May be good.)
It is group represented by these. )
A group represented by the formula: 9-anthryl group or substituted or unsubstituted carbazolyl group, q ₁ and q ₂ are each an integer of 1 to 3, and q ₁ is 2 or 3, a plurality of R ₁₀₃ May be the same or different, and when q ₂ is 2 or 3, the plurality of R ₁₀₄ may be the same or different. )
The photoconductor according to claim 2, comprising a compound represented by the formula: The hole transport material has a general formula
Wherein R ₁₀₈ , R ₁₀₉ and R ₁₁₀ are each independently a hydrogen atom, amino group, alkoxy group, thioalkoxy group, aryloxy group, methylenedioxy group, substituted or unsubstituted alkyl group, halogen atom Or a substituted or unsubstituted aromatic hydrocarbon group, R ₁₀₇ is a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and r, s, t and u are each independently When it is an integer of 1 or more and 4 or less and s is an integer of 2 or more and 4 or less, the plurality of R ₁₀₇ may be the same or different, and r is an integer of 2 or more and 4 or less. in some cases, multiple by R ₁₀₈ may be the same or different, when u is 2 to 4 integer, a plurality of R ₁₀₉ independently represent, it may be the same, different May have, when t is 2 to 4 integer multiple by R ₁₁₀ may be the same or different.)
The photoconductor according to claim 2, comprising a compound represented by the formula: The hole transport material has a general formula
(Wherein Y is a single bond or vinylene group, R ₁₁₁ is a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Ar ₁₀₂ is substituted or unsubstituted. A substituted aromatic hydrocarbon group, R ₁₁₂ is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and R ₁₁₂ is a substituted or unsubstituted alkyl group or substituted Alternatively, when it is an unsubstituted aromatic hydrocarbon group, Ar ₁₀₂ and R ₁₁₂ may form a ring together, and R ₁₁₃ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic carbon group. A hydrogen group, Ar ₁₀₃ is represented by the general formula
Or general formula
(Wherein R ₁₁₄ and R ₁₁₅ are a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, q ₃ and q ₄ are integers of 1 or more and 3 or less, and q ₃ is 2 or 3, The plurality of R ₁₁₄ may be the same or different, and when q ₄ is 2 or 3, the plurality of R ₁₁₅ may be the same or different. )
It is group represented by these. )
5. The photoreceptor according to claim 2, comprising a compound represented by the formula: The hole transport material has a general formula
(In the formula, Z is a single bond or a vinylene group, R ₁₁₆ is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar ₁₀₄ is a substituted or unsubstituted group. A substituted divalent aromatic hydrocarbon group, R ₁₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and B is a general formula
Or general formula
Wherein R ₁₁₈ and R ₁₁₉ are a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a general formula
(Wherein R ₁₂₀ and R ₁₂₁ are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and may form a ring together)
Q ₅ and q ₆ are integers of 1 or more and 3 or less, and when q ₅ is 2 or 3, a plurality of R ₁₁₈ may be the same or different. In addition, when q ₆ is 2 or 3, the plurality of R ₁₁₉ may be the same or different. )
Or a 9-anthryl group or a substituted or unsubstituted carbazolyl group. )
The photoconductor according to claim 2, comprising a compound represented by the formula: The electron transport material has the general formula
(Wherein R ₁₂₂ and R ₁₂₃ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.)
The photoconductor according to claim 1, further comprising a compound represented by the formula: The electron transport material has the general formula
Wherein R ₁₂₄ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R ₁₂₅ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted Or an unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group.)
The photoconductor according to claim 1, further comprising a compound represented by the formula: The electron transport material has the general formula
(Wherein R ₁₂₇ and R ₁₂₈ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.)
The photoconductor according to claim 1, further comprising a compound represented by the formula: The electron transport material has the general formula
(Wherein R ₁₂₉ and R ₁₃₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.)
The photoconductor according to claim 1, further comprising a compound represented by the formula: A photoconductor according to any one of claims 1 to 10,
Charging means for charging the photoreceptor;
Exposure means for exposing the charged photoreceptor to form an electrostatic latent image;
Developing means for developing the electrostatic latent image formed on the photoreceptor with toner to form a toner image;
An image forming apparatus comprising transfer means for transferring a toner image formed on the photoreceptor to a recording medium. A photoconductor according to any one of claims 1 to 10,
A process cartridge which is detachable from a main body of an image forming apparatus.