GB2332200A - Imaging members with improved sensitivity - Google Patents

Imaging members with improved sensitivity Download PDF

Info

Publication number
GB2332200A
GB2332200A GB9827422A GB9827422A GB2332200A GB 2332200 A GB2332200 A GB 2332200A GB 9827422 A GB9827422 A GB 9827422A GB 9827422 A GB9827422 A GB 9827422A GB 2332200 A GB2332200 A GB 2332200A
Authority
GB
United Kingdom
Prior art keywords
imaging member
charge transport
member according
substituted
charge
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
GB9827422A
Other versions
GB9827422D0 (en
Inventor
Ronald Harold Levin
Scott Thomas Mosier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lexmark International Inc
Original Assignee
Lexmark International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lexmark International Inc filed Critical Lexmark International Inc
Publication of GB9827422D0 publication Critical patent/GB9827422D0/en
Publication of GB2332200A publication Critical patent/GB2332200A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/78—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C251/80—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • 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
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • 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
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

Cinnamaldehyde-based hydrazone compounds of the formula wherein A represents a substituted or unsubstituted monocyclic or polycyclic divalent aromatic radical; R represents an N,N-dialkyl amino, N,N-diaryl amino or N-alkyl,N-aryl amino group; each R 2 independently represents an alkyl, halogen, alkoxy group or substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical, with the proviso that at least one R 2 is aromatic; and R 3 and each independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical are suitable for use as a charge transport compound in an imaging member.

Description

1 IMAGING MEMBERS WITH IMPROVED SENSITIVITY 2332200
FIELD OF THE INVENTION
The present invention is directed to aldehyde-based hydrazone compounds and their use as charge transport compounds in imaging members, for example, photoconductors of electrophotographic reproduction devices.
BACKGROUND OF THE INVENTION
In electrophotography, a latent image is created on the surface of an imaging member such as a photoconducting material by selectively exposing areas of the surface to light. A difference in electrostatic charge density is created between those areas on the surface which are exposed to light and those areas on the surface which are not exposed to light. The latent electrostatic image is developed into a visible image by electrostatic toners. The toners are selectively attracted to either the exposed or unexposed portions of the photoconductor surface, depending on the relative electrostatic charges on the photoconductor surface, the development electrode and the toner.
The use of charge transport compounds or molecules in imaging members such as electrophotographic photoconductors is well known in the art. Typically, a layered electrophotographic photoconductor comprises a metal ground plane member on which a charge generation layer (CGL) and a charge transport layer (CTL) are coated. When the charge transport layer is formed on top of the charge generation layer, a negative charge is typically placed on its surface. Conversely, when the charge generation layer is formed on top of the charge transport layer, a positive charge is typically placed on the surface. Generally, the charge generation layer comprises a polymeric binder containing a charge generation compound or molecule while the charge transport layer comprises a polymeric binder containing a charge transport compound or molecule. The charge generation compounds within 1 2 Is the CGI- are sensitive to image-forming radiation and photogenerate electronhole pairs within the CGI- as a result of such radiation. The CTL is usually transparent to the image-forming radiation and the charge transport compounds serve to transport holes to the surface of the photoconductor.
Photoconductors of this type are disclosed in the Adley et al U.S. Patent No. 5,130,215 and the Balthis et al U.S. Patent No. 5,545,499.
The use of hydrazone compounds as charge transport compounds or molecules in a charge transport layer of a photoconductive member is also known in the art as disclosed in the Anderson - et al U.S. Patents Nos.
4,150,987 and 4,362,798, the Ishikawa et al U.S. Patent No. 4,413,045 and the LW et al U.S. Patent No. 5,453,343. A hydrazone compound which is commonly employed in charge transport layers comprises 4(diethylamino)benzaidehyde diphenylhydrazone (DEH). Photoconductors having good sensitivity and durability have been obtained with the use of hydrazone compounds such as DEH as the charge transport compound of a charge transport layer. However, as photoconductors of improved sensitivity and durability and improved performance over extended photoconductor life are continually desired, particularly at lower cost, there is a continuing need for the development of new materials to meet these demands.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide new hydrazone compounds which are suitable, inter alia, for use as charge transport compounds in imaging members, such imaging members including, but not limited to, electrophotographic photosensitive members. It is a further object of the invention to provide new hydrazone compounds suitable for use as charge transport compounds in the charge transport layer of a photoconductor apparatus. It is another object of the invention to provide imaging members which exhibit good sensitivity and mechanical durability. It is yet a further object of the invention to provide imaging members which resist room light fatigue, i.e., a positive or negative fatigue which occurs in 2 3 various conventional imaging members when exposed to fluorescent lighting. It is an additional object of the invention to provide imaging members which are less expensive in cost as compared with various conventional devices.
These and additional objects and advantages are provided by the aldehydebased hydrazone compounds of the present invention which are particularly advantageous for use as charge transport compounds in imaging members. The aldehyde-based hydrazone compounds are of the following Formula (1):
R2 R2 N 1 N R3 15) - R3 R1 R3 wherein A represents a substituted or unsubstituted monocyclic or polycyclic divalent aromatic radical; R, represents an N,N-dialkyl amino, N,N-diaryl amino or N-alkyl,N-aryl amino group; each R2 independently represents an alkyl, alkoxy group or substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical, with the proviso that at least one R2 is aromatic; and R3 and each R3 independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical.
The aldehyde-based hydrazone compounds according to the present invention are advantageous for use as charge transport compounds in imaging members, one embodiment of which comprises photoconductive members. Particularly, the aldehyde-based hydrazone compounds of the invention may be used to provide imaging members with increased sensitivity, improved mechanical durability and/or improved resistance to room light fatigue and/or to provide imaging members which are less expensive than various conventional devices. These and additional objects and advantages 3 4 provided by the compounds and imaging members of the present invention will be further apparent in view of the following detailed description.
BRIEF DESCRIPTION OF THE DRAWING
The present invention as set forth in the detailed description will be more fully understood when viewed in connection with the drawing in which:
Fig. 1 sets forth the sensitivities of a photoconductor employing a aldehyde-based hydrazone compound according to the present invention as compared with a photoconductor employing a - conventional hydrazone compound as described in Example 1; Fig. 2 sets forth the sensitivities of an additional photoconductor comprising an aldehyde-based hydrazone compound according to the present invention as compared with a photoconductor comprising a conventional charge transport molecule as described in Example 2; and is Figs. 3A and 313, respectively, set forth the room light fatigue effects of a photoconductor according to the present invention comprising a aldehydebased hydrazone compound and a conventional photoconductor as described in Example 3.
DETAILED DESCRIPTION
The aldehyde-based hydrazone compounds according to the present invention are of the Formula (I):
R2 R2 N N i R3 ) - R3 A R3 R1..I (0 4 wherein A represents a substituted or unsubstituted monocyclic or polycyclic divalent aromatic radical; R, represents an N,N-dialkyl amino, N,N-diaryl amino or N-alkyl,N-aryl amino group; each R2 independently represents an alkyl, alkoxy group or substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical, with the proviso that at least one R2 is aromatic; and R3 and each R3 independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical.
In one preferred embodiment, A is a substituted or unsubstituted monocyclic or polycyclic divalent aromatic radical of the Formula (11), (111) or (IV):
R4 R4 R4- R4 R4 R 0 R4 or RT' R4 (IV) 9 wherein each R4 independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical. When the R, substituent is attached to the aromatic ring which is linked to the carbon-carbon unsaturated group (i.e., A is of Formula (11) or (IV)), the substituent R, may be in the ortho, meta or para position with respect to the bond attaching A to the carbon-carbon unsaturated group of the aldehydebased compound. Similarly, when A is of Formula (ill), the substituent R, may be in any position relative to the bond attaching A to the carbon-carbon unsaturated group. In a further preferred embodiment, A comprises a phenyl group which, in addition to the substitute IR,, may be substituted or 6 Is unsubstituted. Preferred R4substituents include alkyl groups, for example of from 1 to about 6 carbon atoms.
As set forth above, R, represents an N,N-dialkylamino, N,Ndiarylamino or Walkyl, Warylamino group. Preferred alkyl substituents comprise from 1 to about 6 carbon atoms. In a preferred embodiment, R, comprises an N,1NIdialkylarnino group or an N,N-cliphenylarnino group. In a further preferred embodiment, A is of Formula (11) or ([V) and R, is para to the linkage of the A group to the carbon-carbon unsaturated bond of the aldehyde-based compound.
In a further preferred embodiment, each R2 comprises a substituted or unsubstituted phenyl group, preferably of the following formula (V):
(R5)n -Q wherein n is from 0 to 5 and each R5 independently represents halogen or an alkyl group, for example of from 1 to about 6 carbon atoms. In a preferred embodiment, n is 0, 1 or 2.
R3 and each R3 independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical. Suitable alkyl groups include from 1 to about 6 carbon atoms. Preferably, R3 each R3 represents hydrogen, a Cl-C6 alkyl group or a substituted or unsubstituted phenyl group. Suitable phenyl substituents include halogen and alkyl groups. In a preferred embodiment, R3 each R3 comprises hydrogen or a Cl-C6 alkyl group. In a most preferred embodiment, R3 and each R3 are hydrogen.
The aldehyde-based hydrazone compounds according to the present invention may be obtained by reacting the corresponding cinnamaldehyde derivative with an equimolar amount of the appropriately substituted hydrazine in a suitable solvent. Alternatively, the hydrazine may be added in an excess amount to insure a complete reaction. After the reaction is completed, the hydrazone compounds can be purified by recrystallization.
6 7 Suitable solvents, for example, include Cl-4 alcohols, methyl ethyl ketone, ethyl acetate and the like.
The aldehyde-based hydrazone compounds of the present invention (preferably cinnamaidehyde-based hydrazone compounds) are advantageous for use as charge transport compounds in imaging members, including, but not limited to, photoconductors for use in electrophotographic reproduction devices such as copiers and printers. While specific embodiments of imaging members discussed herein comprise dual layer photoconductors, other imaging members are well known in the art and within the scope of the present invention.
Typically, the photoconductor devices in which the aldehyde-based hydrazone compounds of the present invention may be employed as charge transport materials will comprise a substrate, a charge generating layer which absorbs light and, as a result, generates electrical charge carriers, and a is charge transport layer which transports the charge carriers to the exposed surface of the photoconductor.
The photoconductor substrate may be flexible, for example in the form of a flexible web or a belt, or inflexible, for example in the form of a drum. Typically, the photoconductor substrate is uniformly coated with a thin layer of a metal, preferably aluminum, which functions as an electrical ground plane. In a further preferred embodiment, the aluminum is anodized to convert the aluminum surface into a thicker aluminum oxide surface. Alternatively, the ground plane member may comprise a metallic plate, such as aluminum or nickel, a metallic drum or foil, or a plastic film on which aluminum, tin oxide or indium oxide or the like is vacuum evaporated.
As set forth above, the charge generation layer may be formed on the photoconductor substrate, followed by formation of the charge transport layer, whereby the photoconductor surface is negatively charged, or, conversely, the charge transport layer may be formed on the photoconductor substrate and the charge generation layer is in turn formed on the charge transport layer, whereby the photoconductor surface is positively charged. Typically, 7 8 each of the charge generation and charge transport layers comprise a polymeric binder containing the charge generation compound and charge transport compound, respectively.
Various charge generation compounds which are known in the art are suitable for use in the charge generation layers of imaging members according to the present invention. Organic charge generation compounds including disazo compounds, for example as disclosed in the Ishikawa et al U.S. Patent No. 4,413,045, phthalocyanine dyes, including both metal- free forms such as X-form metal-free phthalocyanines-and the metal - containing phthalocyanines such as titanium-containing phthalocyanines as disclosed in U.S. Patents Nos. 4,664,997, 4,725,519 and 4,777,251, including oxotitanyl phthalocyanine, squaric acid-derived dyes, for example hydroxysquaraine charge generation compounds, and the like are several examples of the many well known charge generating compounds suitable for use in the present imaging members. The charge generation compounds are employed in conventional amounts suitable for providing the charge generation effects. The polymeric binder of the charge generation layer may be any polymeric binder conventionally employed in the art, including, but not limited to, vinyl polymers such as polyvinyl chloride, polyvinyl butyral and polyvinyl acetate, polycarbonate polymers, epoxy resins and copolymers, including polyester carbonate, and the like.
Similar polymers may be employed for the charge transport layer, with polycarbonate polymers and copolymers being preferred for use therein. The aldehyde-based hydrazone compounds of the present invention are included in the charge transport layer in an amount effective to provide the desired electron hole transport function. Suitably, the charge transport layer will include the aldehyde-based hydrazone compounds of the present invention in an amount of from about 20 to about 60 weight percent of the charge transport layer and more preferably in an amount of from about 25 to about 40 weight percent of the charge transport layer.
8 9 Is The photoconductor substrate will be a metal surface on top of which is an anodization layer typically having a thickness from about 0.01 to about 10.0 microns; preferably, from about 0.05 to about 7.0 microns, and most preferably, from about 3.0 to about 5.0 microns. The charge generation layer will have a thickness of from about 0.05 to about 5.0 microns, and the charge transport layer will have a thickness of from about 10.0 to about 35.0 microns. In accordance with techniques known in the art, a barrier layer may be provided between the ground plane and the charge generation layer, typically having a thickness of from about 0.05 to about 2.0 microns. The respective charge generation layer and charge transport layer are formed by dispersing or dissolving the charge generating compound or the charge transport compound, respectively, in a polymeric binder and solvent, coating the resulting dispersion or solution, as the case may be, on the respective underlying layer and drying the coating.
Improvements provided by the aldehyde-based hydrazone compounds according to the present invention when employed as charge transport compounds in imaging members are illustrated in the examples. In the examples and throughout the present specification, parts and percentages are by weight unless otherwise specified.
EXAMPLE1
In this example, two layer photoconductors were made in accordance with conventional techniques. The charge generation layer comprised approximately 35 weight percent hydroxy squaraine (OH-Sq) and approximately 65 weight percent of a polymeric binder comprising a mixture of polyvinyl butyral and epoxy resin [poly(bisphenol-A-coepichlorohydrin) glycidyl end capped, sold as Epon 1009 from Shell Chemical]. In a first photoconductor 1A, the charge transport layer comprised approximately 30 weight percent of a cinnamaidehyde-based hydrazone compound according to the present invention, namely trans-4(diethylamino)cinnamaidehyde diphenylhydrazone, as the charge transport compound and approximately 70 weight percent of a po lycarbonate- based polymeric binder. In a second 9 photoconductor 1 B, the charge transport layer comprised approximately 40 weight percent of a conventional charge transport compound, namely 4(diethylamino)benzaidehyde (DEH), and about 60 weight percent of the po 1 yca rbonate -based polymeric binder.
To determine the sensitivities of the photoconductors of this example, the photoconductors were tested using a sensitometer fitted with electrostatic probes to measure the voltage magnitude of the photoconductor's latent electrostatic image. The sensitometer included a charging source designed to charge the photoconductor to about -700 V. Specifically, the photosensitivity was measured as the amount of light energy, in microjouleS/CM2, required to reduce the photoconductor's voltage from its initial charge of about -700 V to about -100 to -150 V. The results of these measurements are set forth in Fig. 1, The results in Fig. 1 demonstrate that the photoconductor 1A is containing the cinnamaidehyde-based hydrazone compound of the present invention as the charge transport compound in the charge transport layer exhibited improved sensitivity as compared with the photoconductor 113 containing the conventional DEH as the charge transport compound in the charge transport layer. This is a surprising result since the photoconductor 1A containing the cinnama)dehyde-based hydrazone compound of the present invention contained 25% less charge transport compound as compared with the photoconductor 113 containing the conventional DEH charge transport compound. Thus, the cinnamaidehyde-based hydrazone compounds according to the present invention may be used to produce photoconductors which are less expensive as they require lower loadings of charge transport compounds. Additionally, in view of the lower loadings of charge transport compounds, photoconductors having higher integrity may be obtained in that the photoconductors will exhibit lower wear and delarnination rates and therefore longer useful photoconductor life may be achieved.
is EXAMPLE2
Photoconductors 2A and 213 as described in Example 1 were prepared except that in the photoconductors described in this example, the charge generation layer comprised about 45 weight percent (based on total weight of solids) of a type Y oxo-titanyl phthalocyanine (Y-Ti = O[Pcl) charge generation compound in the polyvinyl butyral polymeric binder in place of the hydroxy squaraine charge generation compound described in Example 1. Photoconductor 2A was according to the invention and contained the trans4(diethylamino)cinnamaidehyde diphenylhydrazone- as a charge transport compound. Additionally, a second photoconductor 213 was prepared according to this example wherein the charge transport layer contained a conventional charge transport compound comprising N,Wbis-(3methylphenyi)N,N'-bis-phenyi-benzidine (TPD), which is commonly employed with oxotitanyl phthalocyanine-containing charge generation layers.
The photoconductors of this example were subject to sensitivity measurements in accordance with the procedures set forth in Example 1. The results of these measurements are set forth in Fig. 2. The results set forth in Fig. 2 demonstrate the improved residual voltage exhibited by the photoconductor 2A including the cinnamaidehyde-based hydrazone compound as the charge transport compound of the charge transport layer as compared with the photoconductor 213 comprising conventional TPD, a relatively expensive charge transport compound. Accordingly, the cinnamaidehyde-based hydrazone compounds of the present invention advantageously and unexpectedly allow the formation of a photoconductor having good sensitivity comparable to TPID-containing photoconductors at a relatively lower cost. They also display low cycling fatigue.
EXAMPLE 3
Many photoconductors suffer from a negative fatigue upon exposure to fluorescent light which is typical in room lighting. Negative fatigue adversely affects the image quality and results in the production of light or washed out images. In this example, photoconductors as described in Example 1 were 11 12 subjected to measurement of room light fatigue (RLF). Each of two photoconductors prepared as described in Example 1 were subjected to sensitivity measurements according to the procedures described in Example 1, both before and after exposure to fluorescent light. The results of the sensitivity measurements for the photoconductor 1A employing a ci n namaldeh yde -based hydrazone compound as the charge transport compound according to the present invention and the conventional photoconductor employing DEH as the charge transport compound are set forth in Figs. 3A and 313, respectively.
A comparison of Figs. 3A and 313 demonstrates that while the conventional photoconductor exhibits a noticeable degree of negative room light fatigue (Fig. 313), the photoconductor containing the cinnamaldehydebased hydrazone compound according to the present invention did not exhibit negative room light fatigue (Fig. 3A). Thus, the photoconductor including the is cinnamaidehyde-based hydrazone compound as the charge transport compound will exhibit improved consistency and image quality, particularly in typical office lighting environments. Additionally, the photoconductor including the cinnamaidehyde-based hydrazone compound is advantageous in that it avoids any requirement for an additive to prevent RLF as would commonly be employed in the photoconductor containing the conventionalDEH as the charge transport compound.
The foregoing examples and various preferred embodiments of the present invention set forth herein are provided for illustrative purposes only and are not intended to limit the scope of the invention defined by the claims. Additional embodiments of the present invention and advantages thereof will be apparent to one of ordinary skill in the art and are within the scope of the invention defined by the following claims.
12 13

Claims (20)

  1. We claim:
    An imaging member, comprising a charge transport compound of the formula R2 R2 N 1 N R3 ) - R3 -,A R3 (0 R1 wherein A represents a substituted or unsubstituted monocyclic or polycyclic divalent aromatic radical; R, represents an N,N-dialkyl amino, N,N-diaryl amino or N-alkyl,Waryl amino group; each R2 independently represents an alkyl, alkoxy group or substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical, with the proviso that at least one R2 is aromatic; and R3 and each R3 independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical.
  2. 2. An imaging member according to claim 1, wherein A is of the formula R4 R4 R4 f14 R4 P14 9 R4 or 1 13 14 wherein each R4is independently hydrogen, an alkyl group of from 1 to about 6 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical.
  3. 3. An imaging member according to claim 2, wherein A comprises a phenylene group.
  4. 4. An imaging member according to claim 3, wherein R, comprises an N,Ndialkyl amino group.
  5. 5. An imaging member according to claim 3, wherein R, comprises an N,Ndiethyl amino group.
  6. 6. An imaging member according to claim 1, wherein R3 and each R3 are hydrogen.
  7. 7. An imaging member according to claim 1, wherein A comprises a phenyl group, R, comprises an N,N-dialkyl amino group, and each R3 comprises hydrogen.
  8. 8. An imaging member according to claim 7, wherein at least one R2 comprises a substituted or unsubstituted phenyl group.
  9. 9. An imaging member according to claim 1, wherein the imaging member includes a charge transport layer which comprises from about 20 to about 60 weight percent of the charge transport compound.
  10. 10. An imaging member according to claim 9, wherein the charge transport layer further includes a polymeric binder.
    14
  11. 11. An imaging member according to claim 10, wherein the polymeric binder comprises a polycarbonate polymer or copolymer.
  12. 12. An imaging member according to claim 1, wherein the imaging member includes a charge generating layer comprising a squaraine charge generating material in a polymeric binder.
  13. 13. An imaging member according to claim 1, wherein the imaging member includes a charge generating layer comprising an oxo-titanyl phthalocyanine charge generating material in a polymeric binder.
  14. 14. An imaging member according to claim 1, comprising a ground plane member, a charge generation layer on the ground plane member, and a charge transport layer on the charge generation layer.
  15. 15. An imaging member according to claim 1, comprising a ground plane member, a charge transport layer on the ground plane member, and a charge generation layer on the charge transport layer.
  16. 16. An imaging member, comprising an aluminum ground plane member, a charge generation layer on the ground plane member, and a charge transport layer on the charge generation layer, wherein the charge transport layer comprises a polymeric binder and from about 20 to about 60 weight percent of a charge transport compound of the formula (R5)n N I N \ H R1/_d 16 wherein R, represents an INI,N-dialkyl amino, N,N-diaryl amino or Walkyl, Naryl amino group, each n independently is from 0 to 5 and each R5 10 independently represents halogen or an alkyl group.
  17. 17. An imaging member according to claim 16, wherein R, comprises N,Ndialkylamino.
  18. 18. An imaging member according to claim 17, wherein n is 0.
  19. 19. A compound of the formula R2\ R2 1 R3 f"" R3 A R3 (1) Ri" wherein A represents a substituted or unsubstituted monocyclic or polycyclic divalent aromatic radical; R, represents an N,N-dialkyl amino, N,N-diaryl amino or N-alkyi,N-ar amino group; each R2 independently represents an alky], halogen, alkoxy group or substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical, with the proviso that at least one R2 is aromatic; and R3 and each R3 independently represents hydrogen, alkyl or a substituted or unsubstituted monocyclic or polycyclic monovalent aromatic radical.
  20. 20. A compound according to claim 19, wherein A comprises a phenyl group, R, comprises an KINI-dialkyl amino group, and each R3 comprises hydrogen.
    16
GB9827422A 1997-12-11 1998-12-11 Imaging members with improved sensitivity Withdrawn GB2332200A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US98860097A 1997-12-11 1997-12-11

Publications (2)

Publication Number Publication Date
GB9827422D0 GB9827422D0 (en) 1999-02-03
GB2332200A true GB2332200A (en) 1999-06-16

Family

ID=25534303

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9827422A Withdrawn GB2332200A (en) 1997-12-11 1998-12-11 Imaging members with improved sensitivity

Country Status (1)

Country Link
GB (1) GB2332200A (en)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2092323A (en) * 1980-12-17 1982-08-11 Canon Kk Electrophotographic photosensitive member
JPS57204054A (en) * 1981-06-10 1982-12-14 Canon Inc Electrophotographic receptor
JPS59114545A (en) * 1982-12-21 1984-07-02 Mitsubishi Paper Mills Ltd Electrophotographic sensitive body
US4956277A (en) * 1987-12-09 1990-09-11 Fuji Electric Co., Ltd. Photoconductor comprising charge transporting hydrazone compounds
US4957837A (en) * 1987-10-15 1990-09-18 Fuji Electric Co., Ltd. Photosensitive member for electrophotography containing hydrazone in charge transport layer
JPH04281461A (en) * 1991-03-08 1992-10-07 Ricoh Co Ltd Electrophotographic sensitive material
US5453343A (en) * 1993-02-09 1995-09-26 Industrial Technology Research Institute Hydrazone compounds as charge transport material in photoreceptors
JPH08190215A (en) * 1995-01-12 1996-07-23 Ricoh Co Ltd Electrophotographic photoreceptor

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2092323A (en) * 1980-12-17 1982-08-11 Canon Kk Electrophotographic photosensitive member
JPS57204054A (en) * 1981-06-10 1982-12-14 Canon Inc Electrophotographic receptor
JPS59114545A (en) * 1982-12-21 1984-07-02 Mitsubishi Paper Mills Ltd Electrophotographic sensitive body
US4957837A (en) * 1987-10-15 1990-09-18 Fuji Electric Co., Ltd. Photosensitive member for electrophotography containing hydrazone in charge transport layer
US4956277A (en) * 1987-12-09 1990-09-11 Fuji Electric Co., Ltd. Photoconductor comprising charge transporting hydrazone compounds
JPH04281461A (en) * 1991-03-08 1992-10-07 Ricoh Co Ltd Electrophotographic sensitive material
US5453343A (en) * 1993-02-09 1995-09-26 Industrial Technology Research Institute Hydrazone compounds as charge transport material in photoreceptors
JPH08190215A (en) * 1995-01-12 1996-07-23 Ricoh Co Ltd Electrophotographic photoreceptor

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Chemical Abstract No 100:200880 & JP57204054 (CANON) *
Chemical Abstract No 102:176441 & JP590114545 (MITSUBISHI PAPER MILLS LTD) *
Chemical Abstract No 118:136193 & JP040281461 (RICOH) *
Chemical Abstract No 125:261209 & JP080190215 (RICOH) *

Also Published As

Publication number Publication date
GB9827422D0 (en) 1999-02-03

Similar Documents

Publication Publication Date Title
CA1087438A (en) Photoconductive composition containing a p type organic photoconductor and a charge transfer complex
US5925486A (en) Imaging members with improved wear characteristics
US5330865A (en) Multi-layered electrophotographic element having a mixture of perylene pigments
US4713307A (en) Organic azo photoconductor imaging members
WO2000005628A1 (en) Photoconductor with charge generation binder blend
US6613488B1 (en) Electrophotographic photosensitive material, electrophotographic photoconductor, and method for manufacturing same
US5972549A (en) Dual layer photoconductors with charge generation layer containing hindered hydroxylated aromatic compound
GB2332200A (en) Imaging members with improved sensitivity
US6022657A (en) Methods of making charge generation layers containing charge transport compound, and photoconductors containing the same
JPH0446352A (en) Photosensitive body
JP2586447B2 (en) Photoconductor
JP3095524B2 (en) Electrophotographic photoreceptor
US20020122998A1 (en) Charge transfer layer with hydrazone, acetosol yellow and antioxidant of butylated p-cresol reacted with dicyclopentadiene
JPH03259268A (en) Electrophotographic sensitive body
JPH0118415B2 (en)
JPH0118421B2 (en)
JPH0118419B2 (en)
JPH03282555A (en) Electrophotographic sensitive body
JPH03109554A (en) Electrophotographic sensitive body
JPH0120421B2 (en)
JPH0118418B2 (en)
JPH0486669A (en) Electrophotographic sensitive body
JPH0118422B2 (en)
JPS62237457A (en) Photosensitive body
JPH0120419B2 (en)

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)