EP2790059B1 - Elektrophotographisches lichtempfindliches element, elektrophotographische vorrichtung, prozesskartusche und kondensierte polyzyklische aromatische verbindung - Google Patents

Elektrophotographisches lichtempfindliches element, elektrophotographische vorrichtung, prozesskartusche und kondensierte polyzyklische aromatische verbindung Download PDF

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Publication number
EP2790059B1
EP2790059B1 EP14000813.7A EP14000813A EP2790059B1 EP 2790059 B1 EP2790059 B1 EP 2790059B1 EP 14000813 A EP14000813 A EP 14000813A EP 2790059 B1 EP2790059 B1 EP 2790059B1
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Prior art keywords
group
compound
photosensitive member
electrophotographic photosensitive
reactive functional
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English (en)
French (fr)
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EP2790059A8 (de
EP2790059A2 (de
EP2790059A3 (de
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Shinji Takagi
Koichi Nakata
Nobuo Kosaka
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Canon Inc
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Canon Inc
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Priority claimed from JP2014032154A external-priority patent/JP6391251B2/ja
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/07—Polymeric photoconductive materials
    • G03G5/075—Polymeric photoconductive materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/076—Polymeric photoconductive materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds having a photoconductive moiety in the polymer backbone
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0605—Carbocyclic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0605—Carbocyclic compounds
    • G03G5/0607—Carbocyclic compounds containing at least one non-six-membered ring
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/07—Polymeric photoconductive materials
    • G03G5/075—Polymeric photoconductive materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers
    • G03G5/147—Cover layers
    • G03G5/14708—Cover layers comprising organic material
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers
    • G03G5/147—Cover layers
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to an electrophotographic photosensitive member, and an electrophotographic apparatus and a process cartridge including the electrophotographic photosensitive member.
  • the present invention also relates to a novel condensed polycyclic aromatic compound.
  • Japanese Patent Application Laid-Open No. 2010-211031 describes that the outermost surface layer of an electrophotographic photosensitive member contains a polymerized product of a composition including a melamine compound, and a charge transporting compound having a group represented by -OH, -OCH 3 , -NH 2 , -SH or -COOH.
  • Image deletion is considered to be caused as follows: a material in a surface layer of the electrophotographic photosensitive member is degraded due to ozone, nitrogen oxide and the like generated by charging of the electrophotographic photosensitive member, and moisture is adsorbed to the surface of the electrophotographic photosensitive member to reduce the surface resistance of the surface layer. Image deletion tends to remarkably occur particularly under a high-temperature and high-humidity environment.
  • Japanese Patent Application Laid-Open No. HO8-272126 and Japanese Patent Application Laid-Open No. 2001-242656 describe that a specified additive is contained in an electrophotographic photosensitive member to thereby improve permeability to gas, ozone resistance and image density change of the electrophotographic photosensitive member.
  • US 2004/137346 A1 discloses a positively-charged electrophotographic organic photoreceptor including an electrically conductive support, and a charge transport layer and a charge generating layer sequentially stacked thereon.
  • the present invention is directed to providing an electrophotographic photosensitive member high in wear resistance, and also excellent in suppression of image deletion and potential change, as well as an electrophotographic apparatus and a process cartridge including the electrophotographic photosensitive member. Further, the present invention is directed to providing a condensed polycyclic aromatic compound capable of suppressing image deletion and potential change.
  • an electrophotographic photosensitive member as defined in claims 1-11.
  • an electrophotographic apparatus as defined in claim 13.
  • an electrophotographic photosensitive member having high in wear resistance, and also excellent in suppression of image deletion and potential change, as well as a process cartridge and an electrophotographic apparatus including the electrophotographic photosensitive member can be obtained. Furthermore, according to the present invention, a condensed polycyclic aromatic compound capable of suppressing image deletion and potential change can be obtained.
  • a surface layer of an electrophotographic photosensitive member contains a polymerized product of a composition including a hole transporting compound having a first reactive functional group and a compound having a second reactive functional group reactable with the first reactive functional group. Furthermore, a structure other than the first reactive functional group of the hole transporting compound is a structure having only a carbon atom and a hydrogen atom, or a structure having only a carbon atom, a hydrogen atom and an oxygen atom.
  • the present inventors think that image deletion is caused partially due to chemical alternation of an amine structure in a hole transporting compound contained in a surface layer of a usual electrophotographic photosensitive member. Then, the present inventors have searched a hole transporting compound for electrophotographic photosensitive members free from an amine structure, leading to the present invention.
  • an amine compound in particular, an arylamine compound is most frequently used in order to allow holes to be efficiently injected and conveyed. It is considered that hole transporting properties of the arylamine compound is exhibited by electron donating properties of an amine structure and interaction of a nitrogen atom with an aryl group or a group consisting of carbon atoms having sp2 electron orbital (hereinafter, also referred to as sp2 carbon atoms) around the nitrogen atom. It is considered that an arylamine structure tends to undergo a chemical reaction and the like because of being excellent in hole donating/accepting ability. It is considered that particularly in the process of charging on the surface of an electrophotographic photosensitive member, the arylamine structure tends to undergo degradation such as oxidation by the action of an oxidized gas generated by charging, such as ozone and nitrogen oxide.
  • the arylamine structure is oxidized to result in the increase in polar group on a surface member, thereby allowing a discharge product to be easily attached.
  • the discharge product is attached particularly in a high-temperature and high-humidity environment to cause the reduction in the surface resistance of the surface layer and thus the occurrence of image deletion.
  • the present inventors have intensively studied, and as a result, have found that a polymerized product of a composition including the hole transporting compound of the present invention is used to thereby exert the excellent effects of increasing wear resistance and suppressing image deletion and potential change.
  • the reason for this is because the hole transporting compound of the present invention includes no arylamine structure, specifically includes no nitrogen atom, and thus the hole transporting compound is less easily oxidized than an arylamine compound.
  • the structure other than the first reactive functional group preferably has a conjugate structure having 24 or more sp2 carbon atoms, further preferably 28 or more sp2 carbon atoms, from the viewpoint of hole transporting properties.
  • the conjugate structure means a structure in which sp2 carbon atoms are continuously bonded.
  • the conjugate structure has the property of promoting the delocalization of electrons in a molecule, easily performing charge donating/accepting between molecules.
  • the number of sp2 carbon atoms is 120 or less, and more preferably 60 or less.
  • the conjugate structure can have a condensed polycyclic structure therein.
  • the condensed polycyclic structure means a structure in which 2 or more cyclic structures such as benzene rings are adjacent to each other.
  • the condensed polycyclic structure can be a condensed polycyclic structure in which the number of sp2 carbon atoms is 12 or more.
  • the number of sp2 carbon atoms for forming the condensed polycyclic structure is preferably 14 or more, and more preferably 16 or more.
  • the number of sp2 carbon atoms for forming the condensed polycyclic structure is preferably 20 or less and more preferably 18 or less from the viewpoints of film formability and compatibility with a material for constituting the surface layer.
  • the conjugate structure can be planarly extended. Accordingly, in order to form a planar structure, the condensed polycyclic structure can have a 5-membered ring or a 6-membered ring. While the number of rings for forming the condensed polycyclic structure is 2 or more, the number can be 3 or more in order to more suitably exert hole transporting properties.
  • the ring structure for forming the condensed polycyclic structure preferably has 6 or less rings and more preferably 5 or less rings from the viewpoints of film formation ability and flexibility of a molecule. That is, a condensed polycyclic structure having 3 rings or 4 rings is most preferable.
  • the hole transporting compound of the present invention can have at least one unit (one) of the condensed polycyclic structures as a partial structure.
  • the hole transporting compound preferably has two or more units of the condensed polycyclic structures, more preferably 3 units or more of the condensed polycyclic structures.
  • a hole transport substance preferably has 10 units or less of the condensed polycyclic structures, more preferably 4 units or less of the condensed polycyclic structures in one molecule.
  • the hole transport substance When the hole transport substance has 2 or more of the condensed polycyclic structures, the hole transport substance can have a structure, in which the condensed polycyclic structures are connected to each other by a single bond (the condensed polycyclic structures are directly connected to each other), from the viewpoint of stability against chemical alteration.
  • the condensed polycyclic structure is preferably fluorene, anthracene, phenanthrene, fluoranthene or pyrene because the effects of hole transporting properties and suppression of image deletion are higher.
  • the condensed polycyclic structure is more preferably fluorene or pyrene. Such a condensed polycyclic structure may have a substituent.
  • the number of sp2 carbon atoms in the hole transport substance of the present invention does not include the number of sp2 carbon atoms included in the first reactive functional group.
  • the first reactive functional group includes a hydroxy group, an alkoxy group, a carboxy group, an amino group and a thiol group.
  • a hydroxy group, a methoxy group, a carboxy group, an amino group and a thiol group are preferable.
  • a hydroxy group is further preferable.
  • a compound in which the first reactive functional group of the hole transporting compound of the present invention is replaced with a hydrogen atom can be represented by the following formula (1).
  • the molecular structure of the hole transport substance of the present invention can be roughly classified to a structure of the first reactive functional group and a structure other than the first reactive functional group.
  • the structure of the first reactive functional group is, for example, the above-exemplified structure of the first reactive functional group.
  • the structure other than the first reactive functional group means a structure in which the structure of the first reactive functional group is subtracted from the molecular structure of the hole transport substance.
  • a covalent bond remains in a linkage portion of the structure of the first reactive functional group and the structure other than the first reactive functional group.
  • a structure in which a hydrogen atom is bonded to the remaining covalent bond means the compound in which the first reactive functional group is replaced with a hydrogen atom.
  • R 1 to R 6 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group
  • R 7 represents a group derived from a substituted or unsubstituted arene by loss of 6 hydrogen atoms
  • n represents an integer of 1 to 10, provided that when n represents 2 to 10, partial structures represented by the following formula (2) in the formula (1) may be the same or different.
  • the alkyl group includes a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a cyclopentyl group, a n-hexyl group, a 1-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a cyclohexyl group, a 1-methylhexyl group, a cyclohexylmethyl group, a 4-tert-butylcyclohexyl group, a n-heptyl group, a cyclohept
  • the aralkyl group includes a benzyl group, a phenethyl group, an ⁇ -methylbenzyl group, an ⁇ , ⁇ -dimethylbenzyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, an anthracenylmethyl group, a phenanthrenylmethyl group, a pyrenylmethyl group, a furfuryl group, a 2-methylbenzyl group, a 3-methylbenzyl group, a 4-methylbenzyl group, a 4-ethylbenzyl group, a 4-isopropylbenzyl group, a 4-tert-butylbenzyl group, a 4-n-hexylbenzyl group, a 4-n-nonylbenzyl group, a 3,4-dimethylbenzyl group, a 3-methoxybenzyl group, a 4-methoxybenzyl group, a 4-ethoxybenzyl group
  • the aryl group includes a phenyl group, a biphenylyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthrenyl group, a fluoranthenyl group, a pyrenyl group, a triphenylenyl group, a monovalent group derived from tetracene, a monovalent group derived from chrysene, a monovalent group derived from pentacene, a monovalent group derived from acenaphthene, an acenaphthylenyl group, a monovalent group derived from perylene, a monovalent group derived from corannulene and a monovalent group derived from coronene.
  • the aryl group may be a compound having a structure in which such condensed polycyclic structures having a conjugate structure are linked directly or via a conjugate double bond group.
  • R 7 represents a group in which 6 hydrogen atoms are removed from a substituted or unsubstituted arene.
  • the arene structure in R 7 in addition to a benzene ring, an arene in which a plurality of rings are further linked can be applied.
  • a polycyclic structure having a conjugate structure and having a planar structure can be applied, as described above.
  • the arene structure can be a benzene structure, a naphthalene structure, a fluorene structure, an anthracene structure, a phenanthrene structure, a fluoranthene structure, a pyrene structure, a triphenylene structure, a tetracene structure, a chrysene structure, a pentacene structure, an acenaphthene structure, an acenaphthylene structure, a perylene structure, a corannulene structure or a coronene structure.
  • the arene structure may be a structure in which such arenes are linked to each other directly or via a conjugate double bond group.
  • the arene structure can be in particular a fluorene structure, an anthracene structure, a phenanthrene structure, a fluoranthene structure or a pyrene structure.
  • At least one of R 1 to R 7 preferably represents the condensed polycyclic structure, and two or more of R 1 to R 7 further preferably represent the condensed polycyclic structure.
  • R 7 has a linked structure.
  • Arene structures in R 7 in such a case may be connected to each other directly or via a carbon atom. Arene structures can be connected directly to each other.
  • the condensed polycyclic aromatic compound capable of suppressing image deletion and potential change includes the following compound. That is, a compound having a hydroxy group, a methoxy group, a carboxy group, an amino group or a thiol group, in which the hydroxy group, the methoxy group, the carboxy group, the amino group or the thiol group of the condensed polycyclic aromatic compound is replaced with a hydrogen atom, corresponds to the compound represented by the formula (1).
  • the substituent may be appropriately selected to thereby allow an sp3 carbon atom to be present in a proper proportion.
  • the hole transporting compound preferably has at least one of the first reactive functional group.
  • the hole transporting compound further preferably has two to four reactive functional groups from the viewpoint of compactness of molecules in a film.
  • the molecular weight of the compound represented by the formula (1) can be 300 or more and 3000 or less. When the molecular weight is in the above range, hole transporting properties and film uniformity are sufficiently achieved.
  • the condensed polycyclic aromatic compound capable of suppressing image deletion and potential change includes a compound characterized by the following: namely, the condensed polycyclic aromatic compound having the first reactive functional group, in which the structure other than the first reactive functional group of the condensed polycyclic aromatic compound is a structure having only a carbon atom and a hydrogen atom or a structure having only a carbon atom, a hydrogen atom and an oxygen atom, and additionally, in which the first reactive functional group is a hydroxy group, a methoxy group, a carboxy group, an amino group or a thiol group.
  • a reaction represented by the following reaction formula was performed.
  • a three-neck flask was equipped with a nitrogen introduction tube, a cooling tube, an inner thermometer and the like.
  • Toluene (312 parts), 142 parts of ethanol and 180 parts of an aqueous 10% by mass sodium carbonate solution were mixed, and stirred well using a mechanical stirrer at room temperature for 30 minutes or more with nitrogen-gas bubbling, and nitrogen replacement was performed.
  • the flask was heated and a coupling reaction was performed at reflux temperature (about 74°C). After the reaction was performed under reflux conditions for about 3 hours, the reaction mixture was cooled to room temperature. A separating funnel was used to separate an organic layer from an aqueous layer, and the resulting organic layer was further washed with water. The organic layer was taken out, and dehydrated using anhydrous magnesium sulfate. The magnesium sulfate was removed, and an organic solvent was removed from the organic layer to provide a crude product.
  • the content of the hole transporting compound having the first reactive functional group in the surface layer is preferably 95% by mass or more and 99% by mass or less based on the total mass of the composition.
  • the content is further preferably 97% by mass or more and 99% by mass or less.
  • electric characteristics are further enhanced.
  • the solid content concentration can be higher, the solid content concentration is 99% by mass or less for allowing the compound having a second reactive functional group and other additives to effectively function.
  • the compound having a second reactive functional group of the present invention is a compound having a reactive functional group reactable with the first reactive functional group.
  • the compound having a second reactive functional group is preferably a melamine compound, a guanamine compound, a urea compound, an isocyanate compound or an aniline compound.
  • a melamine compound, a guanamine compound, a urea compound or an isocyanate compound is preferable.
  • a melamine compound, a guanamine compound or an isocyanate compound is more preferable.
  • the melamine compound, the guanamine compound, the urea compound and the aniline compound have a group represented by -CH 2 -OH or a group represented by - CH 2 -O-R as the reactive functional group.
  • the groups may be the same as or different from the first reactive functional group.
  • R represents a hydrogen atom, or a linear or branched alkyl group having 1 or more and 10 or less carbon atoms.
  • the content of the compound having a second reactive functional group in the composition is preferably 0.1% by mass or more and 5% by mass or less, and further preferably 1 % by mass or more and 3% by mass or less. When the content is in the above range, the effects of wear resistance and suppression of image deletion are further exerted.
  • the unit for subjecting the hole transporting compound of the present invention and the compound having a second reactive functional group to a polymerization reaction includes the following. That is, a unit for applying energy such as ultraviolet lay, electron beam and heat, or a unit in which an aid such as a polymerization initiator, and a compound such as an acid, an alkali, and a complex are allowed to co-exist can be used.
  • the surface layer can be formed by applying a surface layer-coating liquid, obtained by dissolving the hole transporting compound of the present invention and the compound having a second reactive functional group in an organic solvent, to form a coat, and drying and curing the resulting coat.
  • the method for curing the coat of the surface layer-coating liquid includes a method for polymerizing the hole transporting compound using heat, light (ultraviolet ray or the like) or radiation (electron beam or the like).
  • the electrophotographic photosensitive member of the present invention is an electrophotographic photosensitive member including a support and a photosensitive layer formed on the support, as described above.
  • the photosensitive layer includes a single layer type photosensitive layer in which a charge generation substance and a charge transport substance are contained in the same layer, and a laminated type (functional separation type) photosensitive layer in which a charge generation layer containing a charge generation substance and a charge transport layer containing a charge transport substance are separated.
  • a laminated type photosensitive layer can be adopted.
  • a laminate configuration of a charge generation layer and a charge transport layer can also be adopted.
  • FIG. 2 A schematic configuration that can be used for the electrophotographic photosensitive member of the present invention is illustrated in FIG. 2 .
  • a support 21, an undercoat layer 22 formed on the support, a charge generation layer 23 formed on the undercoat layer, a charge transport layer 24 formed on the charge generation layer and a surface layer 25 formed on the charge transport layer are laminated.
  • the support for use in the present invention can be a conductive support made of a material having conductivity.
  • the material of the support include metals and alloys, such as iron, copper, gold, silver, aluminum, zinc, titanium, lead, nickel, tin, antimony, indium, chromium, an aluminum alloy and stainless.
  • a metallic support having a covering film formed by vacuum vapor deposition of aluminum, an aluminum alloy, an indium oxide-tin oxide alloy or the like, or a resin support can also be used.
  • a support obtained by impregnating plastic or paper with conductive particles such as carbon black, tin oxide particles, titanium oxide particles and silver particles, or a support containing a conductive resin can also be used.
  • the shape of the support includes a cylinder shape, a belt shape, a sheet shape or a plate shape, and a cylinder shape is most commonly used.
  • the surface of the support may be subjected to a cutting treatment, a roughening treatment, an alumite treatment or the like for the purpose of suppressing an interference fringe by scattering of laser light.
  • a conductive layer may also be provided between the support and the undercoat layer or the charge generation layer described later, for the purpose of suppressing an interference fringe by scattering of laser or the like or covering scratch on the support.
  • the conductive layer can be formed by forming a coat of a conductive layer-coating liquid obtained by subjecting carbon black, a conductive pigment, a resistance-regulating pigment, or the like together with a binder resin to a dispersing treatment, and drying the resulting coat.
  • a compound that is to be cured and polymerized by heating, ultraviolet irradiation, radiation irradiation or the like may also be added to the conductive layer-coating liquid.
  • a conductive layer in which a conductive pigment or a resistance-regulating pigment is dispersed tends to have a roughened surface.
  • the solvent of the conductive layer-coating liquid includes an ether-based solvent, an alcohol-based solvent, a ketone-based solvent and an aromatic hydrocarbon solvent.
  • the thickness of the conductive layer is preferably 0.1 ⁇ m or more and 50 ⁇ m or less, further preferably 0.5 ⁇ m or more and 40 ⁇ m or less, and further more preferably 1 ⁇ m or more and 30 ⁇ m or less.
  • the binder resin for use in the conductive layer includes polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene, a polyvinyl alcohol resin, a polyvinyl acetal resin, a polycarbonate resin, a polyester resin, a polysulfone resin, a polyphenylene oxide resin, a polyurethane resin, a cellulose resin, a phenol resin, a melamine resin, a silicon resin, an epoxy resin and an isocyanate resin.
  • vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene
  • a polyvinyl alcohol resin such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene
  • the conductive pigment and the resistance-regulating pigment include particles of metals (alloys) such as aluminum, zinc, copper, chromium, nickel, silver and stainless, and a pigment obtained by vapor-depositing such a metal (alloy) on the surface of plastic particles.
  • the pigments may be made of particles of metal oxides such as zinc oxide, titanium oxide, tin oxide, antimony oxide, indium oxide, bismuth oxide, tin-doped indium oxide and antimony or tantalum-doped tin oxide. Such pigments may be used singly or in combination of two or more.
  • An undercoat layer (intermediate layer) having a barrier function or an adhesion function may also be provided between the support or the conductive layer and the charge generation layer for the purpose of the improvements in adhesiveness of the charge generation layer, in coatability and in hole-injecting properties from the support, and the protection of the charge generation layer from electrical breakdown or the like.
  • the undercoat layer can be formed by forming a coat of an undercoat layer-coating liquid obtained by dissolving a binder resin in a solvent, and drying the resulting coat.
  • the binder resin for use in the undercoat layer includes a polyvinyl alcohol resin, poly-N-vinylimidazole, a polyethylene oxide resin, ethylcellulose, an ethylene-acrylic acid copolymer, casein, a polyamide resin, an N-methoxymethylated 6-nylon resin, a copolymerized nylon resin, a phenol resin, a polyurethane resin, an epoxy resin, an acrylic resin, a melamine resin or a polyester resin.
  • the undercoat layer may further contain metal oxide particles.
  • the metal oxide particles include particles containing titanium oxide, zinc oxide, tin oxide, zirconium oxide or aluminum oxide.
  • the metal oxide particles may be metal oxide particles whose surface is treated with a surface treatment agent such as a silane coupling agent.
  • the solvent for use in the undercoat layer-coating liquid includes organic solvents such as an alcohol-based solvent, a sulfoxide-based solvent, a ketone-based solvent, an ether-based solvent, an ester-based solvent, an aliphatic halogenated hydrocarbon-based solvent and an aromatic compound.
  • the thickness of the undercoat layer is preferably 0.05 ⁇ m or more and 30 ⁇ m or less, and more preferably 1 ⁇ m or more and 25 ⁇ m or less.
  • the undercoat layer may further contain organic resin fine particles and a leveling agent.
  • the charge generation layer can be formed by applying a charge generation layer-coating liquid obtained by subjecting a charge generation substance together with a binder resin and a solvent to a dispersing treatment, and drying the resulting coat.
  • the charge generation layer may be a film by vapor deposition of the charge generation substance.
  • the charge generation substance for use in the charge generation layer includes an azo pigment, a phthalocyanine pigment, an indigo pigment, a perylene pigment, a polycyclic quinone pigment, a squarylium dye, a pyrylium salt, a thiapyrylium salt, a triphenylmethane dye, a quinacridone pigment, an azulenium salt pigment, a cyanine dye, an anthanthrone pigment, a pyranthrone pigment, a xanthene dye, a quinonimine dye and a styryl dye.
  • Such charge generation substances may be used singly or in combination of two or more.
  • a phthalocyanine pigment and an azo pigment are preferable, and in particular a phthalocyanine pigment is more preferable from the viewpoint of sensitivity.
  • phthalocyanine pigment in particular, oxytitanium phthalocyanine, chlorogallium phthalocyanine and hydroxygallium phthalocyanine exhibit an excellent charge generation efficiency. Furthermore, as the hydroxygallium phthalocyanine, hydroxygallium phthalocyanine crystal of a crystal form having strong peaks at Bragg angles 2 ⁇ , 7.4° ⁇ 0.3° and 28.2° ⁇ 0.3°, in CuK ⁇ characteristic X-ray diffraction can be adopted from the viewpoint of sensitivity.
  • binder resin for use in the charge generation layer examples include polymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene, a polyvinyl alcohol resin, a polyvinyl acetal resin, a polycarbonate resin, a polyester resin, a polysulfone resin, a polyphenylene oxide resin, a polyurethane resin, a cellulose resin, a phenol resin, a melamine resin, a silicon resin and an epoxy resin.
  • vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene
  • a polyvinyl alcohol resin such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene
  • a polyvinyl alcohol resin such as sty
  • the mass ratio of the charge generation substance to the binder resin can be in a range from 1 : 0.3 to 1 : 4.
  • Examples of the dispersing treatment method include a method using a homogenizer, ultrasonic dispersing, a ball mill, a vibration ball mill, a sand mill, Attritor, a roll mill or the like.
  • the solvent for use in the charge generation layer-coating liquid includes an alcohol-based solvent, a sulfoxide-based solvent, a ketone-based solvent, an ether-based solvent, an ester-based solvent, an aliphatic halogenated hydrocarbon-based solvent and an aromatic compound.
  • the charge transport layer is described.
  • the charge transport layer is formed on the charge generation layer.
  • the charge transport layer contains a charge transport substance and a thermoplastic resin.
  • the thermoplastic resin includes a polycarbonate resin and a polyester resin.
  • the thermoplastic resin can be a polycarbonate resin.
  • the charge transport substance for use in the charge transport layer includes a triarylamine-based compound, a hydrazone compound, a stilbene compound, a pyrazoline-based compound, an oxazole-based compound, a triallylmethane-based compound and a thiazole-based compound.
  • Such charge transport substances may be used singly or in combination of two or more.
  • the charge transport layer can be formed by forming a coat of a charge transport layer-coating liquid obtained by dissolving a charge transport substance and a thermoplastic resin in a solvent, and drying the resulting coat.
  • the ratio of the charge transport substance to the thermoplastic resin in the charge transport layer can be 0.3 parts by mass or more and 10 parts by mass or less based on 1 part by mass of the thermoplastic resin.
  • the drying temperature is preferably 60°C or higher and 150°C or lower, and more preferably 80°C or higher and 120°C or lower, from the viewpoint of suppressing cracking of the charge transport layer.
  • the drying time can be 10 minutes or more and 60 minutes or less.
  • the solvent for use in the charge transport layer-coating liquid includes an alcohol-based solvent, a sulfoxide-based solvent, a ketone-based solvent, an ether-based solvent, an ester-based solvent, an aliphatic halogenated hydrocarbon-based solvent and an aromatic hydrocarbon-based solvent.
  • the thickness of the charge transport layer is preferably 5 ⁇ m to 40 ⁇ m, and in particular, more preferably 10 ⁇ m to 35 ⁇ m.
  • the charge transport layer may contain fluorine atom-containing resin particles, silicone-containing resin particles and the like.
  • the charge transport layer may contain metal oxide particles and inorganic particles.
  • the protective layer is described.
  • the protective layer is formed on the charge transport layer, and in such a case, the protective layer is the surface layer.
  • the protective layer contains a polymerized product of a composition including the hole transporting compound having the first reactive functional group, and the compound having a second reactive functional group reactable with the first reactive functional group.
  • the respective compounds are as described above.
  • the thickness thereof is preferably 0.1 ⁇ m or more and 15 ⁇ m or less, and further more preferably 0.5 ⁇ m or more and 10 ⁇ m or less.
  • the solvent for use in the surface layer-coating liquid includes an alcohol-based solvent, a sulfoxide-based solvent, a ketone-based solvent, an ether-based solvent, an ester-based solvent, an aliphatic halogenated hydrocarbon-based solvent and an aromatic hydrocarbon-based solvent.
  • the solvent can be an alcohol-based solvent from the viewpoint of not dissolving the charge transport layer as a lower layer.
  • the surface layer of the electrophotographic photosensitive member may contain a lubricant such as conductive particles, a silicone oil, wax, fluorine atom-containing resin particles including polytetrafluoroethylene particles, silica particles, alumina particles and boron nitride.
  • a lubricant such as conductive particles, a silicone oil, wax, fluorine atom-containing resin particles including polytetrafluoroethylene particles, silica particles, alumina particles and boron nitride.
  • the additives include a coatability improver such as a leveling agent, organic resin particles such as fluorine atom-containing resin particles and acrylic resin particles, and inorganic particles such as silica, titanium oxide and alumina particles.
  • a coatability improver such as a leveling agent
  • organic resin particles such as fluorine atom-containing resin particles and acrylic resin particles
  • inorganic particles such as silica, titanium oxide and alumina particles.
  • any known coating method such as a dip coating method, a spray coating method, a ring coating method, a spin coating method, a roller coating method, a Meyer bar coating method or a blade coating method can also be used.
  • FIG. 1 illustrates one example of a schematic configuration of an electrophotographic apparatus provided with the electrophotographic photosensitive member and the process cartridge of the present invention.
  • reference number 1 represents a cylindrical electrophotographic photosensitive member, which is rotatably driven at a predetermined circumferential speed around an axis 2 in the direction shown by an arrow.
  • the peripheral surface of the electrophotographic photosensitive member 1 to be rotatably driven is uniformly charged to a predetermined positive or negative potential by a charging unit (primary charging unit: charging roller or the like) 3.
  • a charging unit primary charging unit: charging roller or the like
  • the charged peripheral surface is subjected to exposure light (image exposure light) 4 that is emitted from an exposing unit (not illustrated) such as slit exposure or laser beam scanning exposure.
  • an electrostatic latent image according to the intended image is sequentially formed on the peripheral surface of the electrophotographic photosensitive member 1.
  • the voltage to be applied to the charging unit 3 may be a voltage in which an AC component is superimposed to a DC component, or a voltage of only a DC component.
  • the electrostatic latent image formed on the peripheral surface of the electrophotographic photosensitive member 1 is developed by a toner contained in a developer of a developing unit 5 to be formed into a toner image. Then, the toner image formed and supported on the peripheral surface of the electrophotographic photosensitive member 1 is sequentially transferred to a transfer material (paper or the like) 7 with a transfer bias from a transferring unit (transfer roller or the like) 6.
  • the transfer material 7 is taken out from a transfer material feed unit (not illustrated) in synchronous with the rotation of the electrophotographic photosensitive member 1, and fed to a portion (abutting portion) between the electrophotographic photosensitive member 1 and the transferring unit 6.
  • the transfer material 7 to which the toner image is transferred is separated from the peripheral surface of the electrophotographic photosensitive member 1 and introduced to a fixing unit 8, and is subjected to a treatment of fixing the toner image and then printed out outside the apparatus as an image-formed material (printed or copied material).
  • the surface of the electrophotographic photosensitive member 1, on which the toner image is transferred, is cleaned by a cleaning unit 9 so that a transfer residual toner is removed. Then, the electrophotographic photosensitive member 1 is subjected to a discharging treatment with pre-exposure light 10 from a pre-exposing unit (not illustrated), and thereafter repeatedly used for image forming.
  • pre-exposure light 10 from a pre-exposing unit (not illustrated)
  • pre-exposing is not necessarily required.
  • a transferring unit of an intermediate transfer system in which a belt-shaped or drum-shaped intermediate transfer body is used may be adopted.
  • a plurality of constituent elements selected from the electrophotographic photosensitive member 1, the charging unit 3, the developing unit 5, the cleaning unit 9 and the like may be accommodated in a container to be integrally supported as a process cartridge.
  • a process cartridge may be detachably attachable to the main body of the electrophotographic apparatus.
  • the electrophotographic photosensitive member 1, and the charging unit 3, the developing unit 5 and the cleaning unit 9 are integrally supported to be formed into a cartridge, and thus set up to a process cartridge 11 detachably attachable to the main body of the electrophotographic apparatus by using a guiding unit 12 such as a rail provided in the main body of the electrophotographic apparatus.
  • part(s) in Examples means “part(s) by mass”.
  • An aluminum cylinder having a diameter of 30 mm, a length of 357.5 mm and a wall thickness of 1 mm was used as a support (conductive support).
  • silane coupling agent As the silane coupling agent, KBM602 (compound name: N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane) produced by Shin-Etsu Chemical Co., Ltd. was used.
  • the zinc oxide particles surface-treated (80.8 parts) and 0.8 parts of 2,3,4-trihydroxybenzophenone (produced by Wako Pure Chemical Industries, Ltd.) were added to the resulting solution, and were dispersed by a sand mill apparatus using glass beads having a diameter of 0.8 mm at an atmosphere of 23 ⁇ 3°C for 3 hours.
  • the undercoat layer-coating liquid was dip-applied on the aluminum cylinder to form a coat, and the resulting coat was dried at 160°C for 40 minutes to form an undercoat layer having a thickness of 18 ⁇ m.
  • a hydroxygallium phthalocyanine crystal (charge generation substance) of a crystal form having strong peaks at Bragg angles 2 ⁇ ⁇ 0.2°, 7.4° and 28.2°, in CuK ⁇ characteristic X-ray diffraction was prepared.
  • a calixarene compound represented by the following formula (A) 10 parts of a polyvinyl butyral resin (product name: S-Lec BX-1, produced by Sekisui Chemical Co., Ltd.) and 600 parts of cyclohexanone were dispersed by a sand mill apparatus using glass beads having a diameter of 1 mm for 4 hours, 700 parts of ethyl acetate was added thereto to prepare a charge generation layer-coating liquid.
  • the charge generation layer-coating liquid was dip-applied on the undercoat layer to form a coat, and the resulting coat was heated and dried at a temperature of 80°C for 15 minutes to thereby form a charge generation layer having a thickness of 0.17 ⁇ m.
  • the surface layer-coating liquid was applied on the charge transport layer to form a coat, and the coat was heat-treated at 160°C for 1 hour for curing, to form a surface layer having a thickness of 5 ⁇ m as a protective layer.
  • an electrophotographic photosensitive member including the support, the undercoat layer, the charge generation layer, the charge transport layer and the surface layer (protective layer) was produced.
  • the electrophotographic photosensitive member produced was mounted on a cyan station in an electrophotographic apparatus (copier) (product name: iR-ADV C5051) altered, manufactured by Canon Inc., as an evaluation apparatus. Then, the initial potential at 30°C/80%RH, the potential after image formation for 1000 sheets, and the image (fine line) reproducibility were evaluated. With respect to the alteration of the apparatus, the process speed was set to 350 mm/sec.
  • an electrophotographic photosensitive member (for control) mounted on the electrophotographic apparatus was used, and the conditions of a charging apparatus and an exposure apparatus were set so that the initial dark portion potential (VD) and the initial light portion potential (VL) of the electrophotographic photosensitive member were -700V and -200V, respectively. Then, the initial dark portion potential (VD) and the initial light portion potential (VL) of the electrophotographic photosensitive member produced were measured. Image formation was performed for 1000 sheets under the conditions, and the dark portion potential (VD) and the light portion potential (VL) after the image formation for 1000 sheets were measured in the same manner.
  • the image reproducibility was evaluated as follows. First, the total discharge current in a charging step was set to 150 ⁇ A, and then a cassette heater in the apparatus was turned OFF. Thereafter, a test chart having an image rate of 5% was used to perform continuous image formation for 5000 sheets, and the sheets were left to stand for 3 days. Thereafter, an A4 horizontal 1 dot-1 space image of an output resolution of 600 dpi was formed, and the image density in the vicinity of the charging apparatus and the image reproducibility on the whole surface of the A4 image were evaluated as follows. Similarly, the total discharge current was set to 200 ⁇ A, and the image reproducibility was evaluated in the same manner.
  • Each of electrophotographic photosensitive members was produced in the same manner as in Example 1 except that the contents of the hole transporting compound and the melamine compound were changed as shown in Table 1, and the evaluations were performed. The results are shown in Table 1.
  • An electrophotographic photosensitive member was produced in the same manner as in Example 1 except that (I-8) was used as the hole transporting compound, and the evaluations were performed. The results are shown in Table 1.
  • An electrophotographic photosensitive member was produced in the same manner as in Example 5 except that a guanamine compound (Nikalac BL-60 produced by Sanwa Chemical Co., Ltd.) was used instead of the melamine compound, and the evaluations were performed. The results are shown in Table 1.
  • An electrophotographic photosensitive member was produced in the same manner as in Example 5 except that a blocked isocyanate (product name: Sumijule 3175, produced by Sumika Bayer Urethane Co., Ltd.) was used instead of the melamine compound, and the evaluations were performed. The results are shown in Table 1.
  • a blocked isocyanate product name: Sumijule 3175, produced by Sumika Bayer Urethane Co., Ltd.
  • An electrophotographic photosensitive member was produced in the same manner as in Example 5 except that a methylolated urea compound obtained by heating urea together with formaldehyde in the presence of a basic catalyst was used instead of the melamine compound, and the evaluations were performed. The results are shown in Table 1.
  • Each of electrophotographic photosensitive members was produced in the same manner as in Example 1 except that one shown in Table 1 was used as the hole transporting compound, and the evaluations were performed. The results are shown in Table 1.
  • An electrophotographic photosensitive member was produced in the same manner as in Example 1 except that a compound represented by the following formula (6) was used as the hole transporting compound, and the evaluations were performed. The results are shown in Table 1.
  • An electrophotographic photosensitive member was produced in the same manner as in Example 1 except that a compound represented by the following structural formula (7) was used as the hole transporting compound, and the evaluations were performed. The results are shown in Table 1.
  • An electrophotographic photosensitive member was produced in the same manner as in Comparative Example 1 except that 1 part of o-terphenyl (produced by Tokyo Chemical Industry Co., Ltd.) was further added to the components in Comparative Example 1, and the evaluations were performed. The results are shown in Table 1.

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Claims (14)

  1. Elektrophotographisches lichtempfindliches Element, umfassend:
    einen Träger; und
    eine auf dem Träger gebildete lichtempfindliche Schicht,
    wobei eine Oberflächenschicht des elektrophotographischen lichtempfindlichen Elements ein polymerisiertes Produkt einer Zusammensetzung umfasst, die folgendes umfasst:
    eine Löcher transportierende Verbindung mit einer ersten reaktiven funktionellen Gruppe; und
    eine Verbindung mit einer zweiten reaktiven funktionellen Gruppe, die mit der ersten reaktiven funktionellen Gruppe reagieren kann,
    wobei
    eine von der ersten reaktiven funktionellen Gruppe der Löcher transportierenden Verbindung verschiedene Struktur folgendes ist:
    eine aus einem oder mehr Kohlenstoffatomen und einem oder mehr Wasserstoffatomen bestehende Struktur; oder
    eine aus einem oder mehr Kohlenstoffatomen, einem oder mehr Wasserstoffatomen und einem oder mehr Sauerstoffatomen bestehende Struktur.
  2. Elektrophotographisches lichtempfindliches Element nach Anspruch 1,
    wobei die von der ersten reaktiven funktionellen Gruppe der Löcher transportierenden Verbindung verschiedene Struktur eine Struktur ist, die eine konjugierte Struktur mit 24 oder mehr sp2 Kohlenstoffatomen aufweist, und
    die konjugierte Struktur eine kondensierte polyzyklische Struktur mit 12 oder mehr sp2 Kohlenstoffatomen aufweist.
  3. Elektrophotographisches lichtempfindliches Element nach Anspruch 2, wobei die Löcher transportierende Verbindung 2 oder mehr der kondensierten polyzyklischen Strukturen aufweist.
  4. Elektrophotographisches lichtempfindliches Element nach Anspruch 2 oder 3, wobei die kondensierten polyzyklischen Strukturen miteinander über eine Einzelbindung verbunden sind.
  5. Elektrophotographisches lichtempfindliches Element nach einem der Ansprüche 2 bis 4, wobei die kondensierte polyzyklische Struktur einen 5-gliedrigen Ring oder einen 6-gliedrigen Ring aufweist.
  6. Elektrophotographisches lichtempfindliches Element nach einem der Ansprüche 2 bis 5, wobei die von der ersten reaktiven funktionellen Gruppe der Löcher transportierenden Verbindung verschiedene Struktur eine konjugierte Struktur mit 28 oder mehr sp2 Kohlenstoffatomen aufweist.
  7. Elektrophotographisches lichtempfindliches Element nach Anspruch 1, wobei eine Verbindung, in der die erste reaktive funktionelle Gruppe der Löcher transportierenden Verbindung durch ein Wasserstoffatom ersetzt ist, eine durch die folgende Formel (1) dargestellte Verbindung ist:
    Figure imgb0117
    wobei in der Formel (1), R1 bis R6 jeweils unabhängig ein Wasserstoffatom, eine substituierte oder unsubstituierte Alkylgruppe, eine substituierte oder unsubstituierte Aralkylgruppe oder eine substituierte oder unsubstituierte Arylgruppe darstellen, R7 eine von einem substituierten oder unsubstituierten Aren durch Verlust von 6 Wasserstoffatomen abgeleitete Gruppe darstellt und n eine ganze Zahl von 1 bis 10 darstellt, mit der Maßgabe, dass wenn n 2 bis 10 darstellt, durch die folgende Formel (2) dargestellte Teilstrukturen in der Formel (1) gleich oder verschieden sein können:
    Figure imgb0118
  8. Elektrophotographisches lichtempfindliches Element nach Anspruch 7, wobei das Aren von R7 in der Formel (1) Fluoren, Anthracen, Phenanthren, Fluoranthen oder Pyren ist.
  9. Elektrophotographisches lichtempfindliches Element nach einem der Ansprüche 1 bis 8,
    wobei die erste reaktive funktionelle Gruppe eine Hydroxygruppe, eine Methoxygruppe, eine Carboxygruppe, eine Aminogruppe oder eine Thiolgruppe ist, und
    die Verbindung mit einer zweiten reaktiven funktionellen Gruppe eine Melaminverbindung, eine Guanaminverbindung, eine Harnstoffverbindung oder eine Isocyanatverbindung ist.
  10. Elektrophotographisches lichtempfindliches Element nach Anspruch 9,
    wobei die erste reaktive funktionelle Gruppe eine Hydroxygruppe ist, und
    die Verbindung mit einer zweiten reaktiven funktionellen Gruppe eine Isocyanatverbindung, eine Melaminverbindung oder eine Guanaminverbindung ist.
  11. Elektrophotographisches lichtempfindliches Element nach einem der Ansprüche 1 bis 10, wobei ein Molekulargewicht der durch die Formel (1) dargestellten Verbindung 300 oder mehr und 3000 oder weniger beträgt.
  12. Prozesskartusche, die das elektrophotographische lichtempfindliche Element nach einem der Ansprüche 1 bis 11 und wenigstens eine Einheit ausgewählt aus der Gruppe bestehend aus einer Ladeeinheit, einer Entwicklungseinheit, einer Transfereinheit und einer Reinigungseinheit integral trägt, wobei die Prozesskartusche an einen Hauptkörper einer elektrophotographischen Vorrichtung abnehmbar anbringbar ist.
  13. Elektrophotographische Vorrichtung, umfassend das elektrophotographische lichtempfindliche Element nach einem der Ansprüche 1 bis 11, eine Ladeeinheit, eine Belichtungseinheit, eine Entwicklungseinheit und eine Transfereinheit.
  14. Kondensierte polyzyklische aromatische Verbindung mit einer ersten reaktiven funktionellen Gruppe,
    wobei
    eine von der ersten reaktiven funktionellen Gruppe der kondensierten polyzyklischen aromatischen Verbindung verschiedene Struktur folgendes ist:
    eine aus einem oder mehr Kohlenstoffatomen und einem oder mehr Wasserstoffatomen bestehende Struktur; oder
    eine aus einem oder mehr Kohlenstoffatomen, einem oder mehr Wasserstoffatomen und einem oder mehr Sauerstoffatomen bestehende Struktur,
    wobei die erste reaktive funktionelle Gruppe eine Hydroxygruppe, eine Methoxygruppe, eine Carboxygruppe, eine Aminogruppe oder eine Thiolgruppe ist, und
    die von der ersten reaktiven funktionellen Gruppe der kondensierten polyzyklischen aromatischen Verbindung verschiedene Struktur eine Struktur ist, die eine konjugierte Struktur mit 24 oder mehr sp2 Kohlenstoffatomen aufweist.
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