CA1126564A - Imaging member having a charge transport layer of terphenyl diamine in a polycarbonate resin - Google Patents
Imaging member having a charge transport layer of terphenyl diamine in a polycarbonate resinInfo
- Publication number
- CA1126564A CA1126564A CA363,619A CA363619A CA1126564A CA 1126564 A CA1126564 A CA 1126564A CA 363619 A CA363619 A CA 363619A CA 1126564 A CA1126564 A CA 1126564A
- Authority
- CA
- Canada
- Prior art keywords
- selenium
- layer
- group
- charge transport
- transport layer
- 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.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- 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
- G03G5/06144—Amines arylamine diamine
- G03G5/061446—Amines arylamine diamine terphenyl-diamine
Abstract
Abstract of the Disclosure An imaging member comprising a charge generation layer comprising a layer of photoconductive material and a contiguous charge transport layer of a polycarbonate resin material having dispersed therein from about 25 to about 75 percent by weight of one or more diamine compound having the general formula:
Description
~12~;S6~
IMAGING MEMBER
Background of the Invention This invention relates in general to xerography and more specifi-cally to a novel photosensitive device.
s In the art of more or less conventional xerography9 a xerographic plate containing a photoconductive insulating layer is imaged by first uniformly electrostatically charging its surface. The plate is then exposed to a pattern of activating electromagnetic radiation such as light, which selectively dissipates charge in the illuminated areas of the photoconductive insulator resulting in a latent electrostatic image corresponding to the pattern of light-struck and nonlight-struck areas. The latent electrostatic image may then be developed to form a visible im~ge by depositing finely divided electroscopic marking particles on the surface of the photocondu~
tive insulating layer.
In recent years, interest has been shown in flexible electrophoto-graphic plates for use in high speed office copying machines. Some of these plates are multilayered devices comprising, a conductive substrate, an adhesive blocking interface layer, a charge generation layer and a charge transport layer. The charge transport layer comprises an organic charge transport molecule dissolved or dispersed in a polymeric matrix material.
This layer is substantially nonabsorbing in the spectral region of intended use, i.e. visible light, but is "active" in that it allows (1) injection of photo-generated charge from the charge generation layer and (2) efficient transport of these charges to the surface of the transport layer to discharge a surface charge thereon.
One of the parameters limiting the performance of these structures is the charge carrier mobility in the charge transport layer. When a structure such as this is employed in the above-described xerographic process, during the exposure step light is absorbed in the photogenerator layer creating free charge carriers. These charge carriers are then injected Into and transported across the charge transport layer to the surface thereof. The charge carrier mobility or the velocity determines the time of transit across the transport layer. The maximum discharge of the light exposed area is obtained if the injected charge carrier has completely traversed the transport layer before the photoreceptor belt arrives at the development station. In materials with low charge carrier mobilities, the `- 11;265~4 carrier will be part way through the charge transport layer when the photoreceptor belt arrives at the development station giving rise to less than maximum discharge of the photoreceptor.
The art is constantly searching for charge transport layers having high carrier mobility so that the time between exposure and development can be reduced without sacrificing xerographic efficiency. By reducing this time period, faster machines are possible.
Objects of Aspects of the Invention It is therefore an object of an aspect of the invention to provide a novel photosensitive device having a charge transport layer capable of highl~ efficient trans-port of injected charges.
It is an object of an aspect of this invention to provide an electrophotographic device which permits faster machine operation.
Prior Art Statement In U.S. Patent 4,078,925, there is disclosed 20 classes of charge transport compounds which may be added to inactive polymeric matrix materials for use as a charge transport layer in an electrophotographic imaging member.
It is believed that this is the prior art most pertinent to the instant invention.
Summary of the Invention In accordance w_th one aspect of this invention there is provided an imaging member comprising a charge generation layer comprising a layer of photoconductive material and a contiguous charge transport layer of a 30 polycarbonate resin material having dispersed therein from about 25 to about 75 percent by weight of one or more diamine compoundshaving the general formula hereinaf-ter set out, the photoconductive layer exhibiting the capability of photogeneration of holes and injection of 35 said holes and said charge transport layer being sub-stantially nonabsorbing in the spectral region at which the photoconductive layer generates and injects photo-A generated holes but being capable of supporting the llZ~
-2a-injection of photogenerated holes from said photoconductive layer and transporting said holes through said charge transport layer:
iS6~
~X~
N~{~N
wherein Xl and X2 are independently selected from the group consisting of a lower alkyl group having from 1 to about 4 carbon atoms (e.g. methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, n-butyl, etc.), chlorine in the ortho, meta or para position, a para phenyl group and combinations thereof. At least two of the phenyl substituents on the N atoms must be substituted with said alkyl group, said chloride atom, said para phenyl group or a combination of these substituents.
Included within this structure are the following compounds:
N,N'-diphenyl-N,N'-bis(3-methylphenyl)[~terphenyl]-4,4"-diamine; N,N'-bis-(2-methylphenyl~N,N'bis[4-(1-butyl)phenyl] {p-terphenyl] -4,4"-diamine; N,-N'-diphenyl-N,N'-bis(4-methylphenyl)[p-terphenyl~-4,4"-diamine; N,N'bis(bi-phenyl)-N,N'-(3-methylphenyl)[p-terphenyl]-4,~"-diamine; N,N'-diphenyl-~,-N'-bis(3-chlorophenyl)[p-terphenyl] -4,4"-diamine.
Brief Description of the Drawing The figure is a schematic illustration of one of the members of the instant invention which comprise a photoreceptor having a charge generQtion layer overcoated with a charge transport layer.
Detailed Description of the I)rawing Referring to the figure, reference character 30 designates an imaging member which comprises a supporting substrate 11 having a charge generation layer 12 thereon. Substrate 11 is preferably comprised of any suitable conductive material. Typical conductors comprise aluminum, steel, nickel, brass or the like. The substrate may be rigid or flexible and of any convenient thickness. Typical substrates include flexible belts of sleeves, sheets, webs, plates, cylinders and drums. The substrate or support may also comprise a composite structure such as a thin conductive coating contained ~12656~a on a paper base; a plastic coated with a thin conductive layer such as aluminum, nickel or copper iodine; or glass coated with a thin conductive coating of chromium or tin oxide.
In addition, if desired, an electrically insulating substrate may be 5 used. In this case, an electric charge, equivalent to a conductive layer, may be placed upon the insulating member by double corona charging techniques weU known and disclosed in the art. Other modifications using an insulating substrate or no substrate at all include placing the imaging member on a - conductive backing member or plate in charging the surface while in contact 10 with said backing member. Subsequent to im&ging, the imaging member may then be stripped from the conductive backing.
Generator layer 12 contains photoconductive particles dispersed randomly without orientation in binder 14. Binder material 14 may comprise any electricaUy insulating resin such as those disclosed in Middleton et ~1 15 U.S. Patent 3,121,006. Specific examples are polystyrene, acrylic and methacrylic ester polymers, polyvinylchlorides, etc. When using an electrically inactive or insulating resin, it is essential that there be partid~to-particle contact between the photoconductive particles. This necessi-tates that the photoconductive material be present in an amount of at least 20 10 percent by volume of the binder layer with no limit on the maximum amount of photoconductor in the binder layer. If the matrix or binder comprises an active material, e.g. poly-N-vinylcarbazde, the photoconduc-tive material need only comprise about 1 percent or less by volume of the binder layer with no limit on the maximum amount of photoconductor in the 25 binder layer. The thickness of binder layer 12 is not critical. Layer thicknesses from about 0.05 to 40.0 microns have been found to be sati8factory.
The photoconductive particles 13 may be any material capable of photogenerating holes and injecting photogenerated holes into the contiguous 30 charge transport layer 15. Any suitable inorganic or organic photoconductor and mixtures thereoi may be employed. Inorganic materials include Inorganic crystaUine photoconductive compounds and inorganic photoconduc-tive glasses. Typical inorganic compounds include cadmium sulfoselenide, cadmium selenide, cadmium sulfide and mi~ctures thereof. Typical inorganic 35 photoconductive glasses include amorphous selenium and selenium aUoys such as selenium-tellurium, selenium-tellurium-arsenic and selenium-arsenic ,, ~ ~656~
and mixtures thereof. Selenium may also be used in a crystalline form known as trigonal selenium. Typical organic photoconductive materials which may be used as charge generators include phthalocyanine pigment such as the X-form of metal free phthalocyanine described in U.S. Patent 3,357,989 to Byrne et al; metal phthalocyanines such as copper phthalocya-nine; quinacridones available from duPont under the tradename Monastral Red, Monastrq1 Violet and Monastral Red Y; substituted 2,4-diamino-triazines disclosed by Weinberger in U.S. Patent 3,445,227; triphenodioxa-zines disclosed by Weinberger in U.S. Patent 3,442,781; polynuclear aromatic quinones available from Allied Chemic~l Corporation under the tradename Indo Double Scarlet, Indofast Violet Lake B, Indofast Brilliant Scarlet and Indofast Orange. The photoconductive particles may be present in the generator layer in from 0.5 percent to about 95 percent by volume depending upon the character of the binder material.
It is to be understood that the generator layer need not be dispersed in photoconductive particles in a resin binder, but can be a homogeneous layer, such as, amorphous selenium, selenium alloys, e.g.
selenium-tellurium-arsenic alloys and, in fact, any other charge generating photoconductive material which can withstand a minimum flexing stress required in a flexible photoreceptor.
Active layer 15 comprises a transparent electrically inactive polycarbonate resinous material having dispersed therein from about 25 to 75 percent by weight of one or more of the diamines within the scope of the structural formula defined above. In general, the thickness of active layer 15 is from about 5 to 100 microns, but thicknesses outside this range can also be used.
The preferred polycarbonate resins for the transport layer have a molecular weight of from about 20,000 to about 120,000 more preferably from about 50,000 to 120,000. Materials most preferred as the electrically inactive resinous material are poly(4,4"-isopropylidene-diphenylene carbon-ate) having molecular weights of from about 25,000 to about 40,000, available as Lexan~ 145, and from about 40,000 to about 45,000, available AS
Lexan~ 141, both the General Electric Company; and from about 50,000 to about 120,000, available as Makrolon~ from Farbenfabricken Bayer AG; and from about 20,000 to about 50,û00, available as Merlon~ from Mobay Chemical Company. The diamines of the instant invention are soluble to an ~Z6564 unusually high degree which appears to account in part for the high rate of discharge of the devices herein.
Active layer 15 as described above, is substantially nonabsorbing to light in the wavelength region employed to generate holes in the photo-conductive layer. This preferred range for xerographic utility is from about 4000 to about 8000 angstrom units. In addition, the photoconductor should be responsive to all wavelengths from 4000 to 8000 angstrom units if panchromatic responses are required. All photoconducto~active material combinations of the instant invention shall result in the injection and subsequent transport of holes across the physical interface between the photoconductor and the active material.
The following examples further specifically define the present invention with respect to the method of making the photosensitive member.
The percentages are by weight unless otherwise indicated.
E~ample I
Preparation of N,N'-bis(3-methylphenyl)-N,N'-bis[4-(1-butyl)-phenyl] -~P-terphenyl] -4,4"-diamine.
A 250 ml three necked round bottom flask equipped with a mechanical stirrer and purged with argon was charged with 14.34 grams (0.06 moles) of 3-methyl-4"-(1-butyl)diphenylamine, 9.64 grams (.02 moles) of 4~4n_ diiodoterphenyl, 15 grams (0.11 moles) of potassium carbonate, 10 grams of copper bronze and 50 milliliters of C13-C15 aliphatic hydrocarbons, i.e.
SoltrolQ 170 (Phillips Chemical Company). The mixture was heated for 18 hours at 210C. The product was isolated by the addition of 200 mls of n-octane and hot filtered to remove inorganic solids. The product crystallized out on cooling and was isolated by filtration. Treatment with alumina yielded pure N,N'-bis(3-methylphenyl)-N,N'-bis[4-(1-butyl)-phenyll-~p-ter-phenyll-4,4"-diamine in approximately 75% yield.
Example II
; 30 A 0.5 micron thick layer of amorphous selenium is vapor deposited on a 3 mil aluminum substrate by a conventional vacuum deposition technique such as those disclosed in Bixby in U.S. Patent
IMAGING MEMBER
Background of the Invention This invention relates in general to xerography and more specifi-cally to a novel photosensitive device.
s In the art of more or less conventional xerography9 a xerographic plate containing a photoconductive insulating layer is imaged by first uniformly electrostatically charging its surface. The plate is then exposed to a pattern of activating electromagnetic radiation such as light, which selectively dissipates charge in the illuminated areas of the photoconductive insulator resulting in a latent electrostatic image corresponding to the pattern of light-struck and nonlight-struck areas. The latent electrostatic image may then be developed to form a visible im~ge by depositing finely divided electroscopic marking particles on the surface of the photocondu~
tive insulating layer.
In recent years, interest has been shown in flexible electrophoto-graphic plates for use in high speed office copying machines. Some of these plates are multilayered devices comprising, a conductive substrate, an adhesive blocking interface layer, a charge generation layer and a charge transport layer. The charge transport layer comprises an organic charge transport molecule dissolved or dispersed in a polymeric matrix material.
This layer is substantially nonabsorbing in the spectral region of intended use, i.e. visible light, but is "active" in that it allows (1) injection of photo-generated charge from the charge generation layer and (2) efficient transport of these charges to the surface of the transport layer to discharge a surface charge thereon.
One of the parameters limiting the performance of these structures is the charge carrier mobility in the charge transport layer. When a structure such as this is employed in the above-described xerographic process, during the exposure step light is absorbed in the photogenerator layer creating free charge carriers. These charge carriers are then injected Into and transported across the charge transport layer to the surface thereof. The charge carrier mobility or the velocity determines the time of transit across the transport layer. The maximum discharge of the light exposed area is obtained if the injected charge carrier has completely traversed the transport layer before the photoreceptor belt arrives at the development station. In materials with low charge carrier mobilities, the `- 11;265~4 carrier will be part way through the charge transport layer when the photoreceptor belt arrives at the development station giving rise to less than maximum discharge of the photoreceptor.
The art is constantly searching for charge transport layers having high carrier mobility so that the time between exposure and development can be reduced without sacrificing xerographic efficiency. By reducing this time period, faster machines are possible.
Objects of Aspects of the Invention It is therefore an object of an aspect of the invention to provide a novel photosensitive device having a charge transport layer capable of highl~ efficient trans-port of injected charges.
It is an object of an aspect of this invention to provide an electrophotographic device which permits faster machine operation.
Prior Art Statement In U.S. Patent 4,078,925, there is disclosed 20 classes of charge transport compounds which may be added to inactive polymeric matrix materials for use as a charge transport layer in an electrophotographic imaging member.
It is believed that this is the prior art most pertinent to the instant invention.
Summary of the Invention In accordance w_th one aspect of this invention there is provided an imaging member comprising a charge generation layer comprising a layer of photoconductive material and a contiguous charge transport layer of a 30 polycarbonate resin material having dispersed therein from about 25 to about 75 percent by weight of one or more diamine compoundshaving the general formula hereinaf-ter set out, the photoconductive layer exhibiting the capability of photogeneration of holes and injection of 35 said holes and said charge transport layer being sub-stantially nonabsorbing in the spectral region at which the photoconductive layer generates and injects photo-A generated holes but being capable of supporting the llZ~
-2a-injection of photogenerated holes from said photoconductive layer and transporting said holes through said charge transport layer:
iS6~
~X~
N~{~N
wherein Xl and X2 are independently selected from the group consisting of a lower alkyl group having from 1 to about 4 carbon atoms (e.g. methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, n-butyl, etc.), chlorine in the ortho, meta or para position, a para phenyl group and combinations thereof. At least two of the phenyl substituents on the N atoms must be substituted with said alkyl group, said chloride atom, said para phenyl group or a combination of these substituents.
Included within this structure are the following compounds:
N,N'-diphenyl-N,N'-bis(3-methylphenyl)[~terphenyl]-4,4"-diamine; N,N'-bis-(2-methylphenyl~N,N'bis[4-(1-butyl)phenyl] {p-terphenyl] -4,4"-diamine; N,-N'-diphenyl-N,N'-bis(4-methylphenyl)[p-terphenyl~-4,4"-diamine; N,N'bis(bi-phenyl)-N,N'-(3-methylphenyl)[p-terphenyl]-4,~"-diamine; N,N'-diphenyl-~,-N'-bis(3-chlorophenyl)[p-terphenyl] -4,4"-diamine.
Brief Description of the Drawing The figure is a schematic illustration of one of the members of the instant invention which comprise a photoreceptor having a charge generQtion layer overcoated with a charge transport layer.
Detailed Description of the I)rawing Referring to the figure, reference character 30 designates an imaging member which comprises a supporting substrate 11 having a charge generation layer 12 thereon. Substrate 11 is preferably comprised of any suitable conductive material. Typical conductors comprise aluminum, steel, nickel, brass or the like. The substrate may be rigid or flexible and of any convenient thickness. Typical substrates include flexible belts of sleeves, sheets, webs, plates, cylinders and drums. The substrate or support may also comprise a composite structure such as a thin conductive coating contained ~12656~a on a paper base; a plastic coated with a thin conductive layer such as aluminum, nickel or copper iodine; or glass coated with a thin conductive coating of chromium or tin oxide.
In addition, if desired, an electrically insulating substrate may be 5 used. In this case, an electric charge, equivalent to a conductive layer, may be placed upon the insulating member by double corona charging techniques weU known and disclosed in the art. Other modifications using an insulating substrate or no substrate at all include placing the imaging member on a - conductive backing member or plate in charging the surface while in contact 10 with said backing member. Subsequent to im&ging, the imaging member may then be stripped from the conductive backing.
Generator layer 12 contains photoconductive particles dispersed randomly without orientation in binder 14. Binder material 14 may comprise any electricaUy insulating resin such as those disclosed in Middleton et ~1 15 U.S. Patent 3,121,006. Specific examples are polystyrene, acrylic and methacrylic ester polymers, polyvinylchlorides, etc. When using an electrically inactive or insulating resin, it is essential that there be partid~to-particle contact between the photoconductive particles. This necessi-tates that the photoconductive material be present in an amount of at least 20 10 percent by volume of the binder layer with no limit on the maximum amount of photoconductor in the binder layer. If the matrix or binder comprises an active material, e.g. poly-N-vinylcarbazde, the photoconduc-tive material need only comprise about 1 percent or less by volume of the binder layer with no limit on the maximum amount of photoconductor in the 25 binder layer. The thickness of binder layer 12 is not critical. Layer thicknesses from about 0.05 to 40.0 microns have been found to be sati8factory.
The photoconductive particles 13 may be any material capable of photogenerating holes and injecting photogenerated holes into the contiguous 30 charge transport layer 15. Any suitable inorganic or organic photoconductor and mixtures thereoi may be employed. Inorganic materials include Inorganic crystaUine photoconductive compounds and inorganic photoconduc-tive glasses. Typical inorganic compounds include cadmium sulfoselenide, cadmium selenide, cadmium sulfide and mi~ctures thereof. Typical inorganic 35 photoconductive glasses include amorphous selenium and selenium aUoys such as selenium-tellurium, selenium-tellurium-arsenic and selenium-arsenic ,, ~ ~656~
and mixtures thereof. Selenium may also be used in a crystalline form known as trigonal selenium. Typical organic photoconductive materials which may be used as charge generators include phthalocyanine pigment such as the X-form of metal free phthalocyanine described in U.S. Patent 3,357,989 to Byrne et al; metal phthalocyanines such as copper phthalocya-nine; quinacridones available from duPont under the tradename Monastral Red, Monastrq1 Violet and Monastral Red Y; substituted 2,4-diamino-triazines disclosed by Weinberger in U.S. Patent 3,445,227; triphenodioxa-zines disclosed by Weinberger in U.S. Patent 3,442,781; polynuclear aromatic quinones available from Allied Chemic~l Corporation under the tradename Indo Double Scarlet, Indofast Violet Lake B, Indofast Brilliant Scarlet and Indofast Orange. The photoconductive particles may be present in the generator layer in from 0.5 percent to about 95 percent by volume depending upon the character of the binder material.
It is to be understood that the generator layer need not be dispersed in photoconductive particles in a resin binder, but can be a homogeneous layer, such as, amorphous selenium, selenium alloys, e.g.
selenium-tellurium-arsenic alloys and, in fact, any other charge generating photoconductive material which can withstand a minimum flexing stress required in a flexible photoreceptor.
Active layer 15 comprises a transparent electrically inactive polycarbonate resinous material having dispersed therein from about 25 to 75 percent by weight of one or more of the diamines within the scope of the structural formula defined above. In general, the thickness of active layer 15 is from about 5 to 100 microns, but thicknesses outside this range can also be used.
The preferred polycarbonate resins for the transport layer have a molecular weight of from about 20,000 to about 120,000 more preferably from about 50,000 to 120,000. Materials most preferred as the electrically inactive resinous material are poly(4,4"-isopropylidene-diphenylene carbon-ate) having molecular weights of from about 25,000 to about 40,000, available as Lexan~ 145, and from about 40,000 to about 45,000, available AS
Lexan~ 141, both the General Electric Company; and from about 50,000 to about 120,000, available as Makrolon~ from Farbenfabricken Bayer AG; and from about 20,000 to about 50,û00, available as Merlon~ from Mobay Chemical Company. The diamines of the instant invention are soluble to an ~Z6564 unusually high degree which appears to account in part for the high rate of discharge of the devices herein.
Active layer 15 as described above, is substantially nonabsorbing to light in the wavelength region employed to generate holes in the photo-conductive layer. This preferred range for xerographic utility is from about 4000 to about 8000 angstrom units. In addition, the photoconductor should be responsive to all wavelengths from 4000 to 8000 angstrom units if panchromatic responses are required. All photoconducto~active material combinations of the instant invention shall result in the injection and subsequent transport of holes across the physical interface between the photoconductor and the active material.
The following examples further specifically define the present invention with respect to the method of making the photosensitive member.
The percentages are by weight unless otherwise indicated.
E~ample I
Preparation of N,N'-bis(3-methylphenyl)-N,N'-bis[4-(1-butyl)-phenyl] -~P-terphenyl] -4,4"-diamine.
A 250 ml three necked round bottom flask equipped with a mechanical stirrer and purged with argon was charged with 14.34 grams (0.06 moles) of 3-methyl-4"-(1-butyl)diphenylamine, 9.64 grams (.02 moles) of 4~4n_ diiodoterphenyl, 15 grams (0.11 moles) of potassium carbonate, 10 grams of copper bronze and 50 milliliters of C13-C15 aliphatic hydrocarbons, i.e.
SoltrolQ 170 (Phillips Chemical Company). The mixture was heated for 18 hours at 210C. The product was isolated by the addition of 200 mls of n-octane and hot filtered to remove inorganic solids. The product crystallized out on cooling and was isolated by filtration. Treatment with alumina yielded pure N,N'-bis(3-methylphenyl)-N,N'-bis[4-(1-butyl)-phenyll-~p-ter-phenyll-4,4"-diamine in approximately 75% yield.
Example II
; 30 A 0.5 micron thick layer of amorphous selenium is vapor deposited on a 3 mil aluminum substrate by a conventional vacuum deposition technique such as those disclosed in Bixby in U.S. Patent
2,753,278 and 2,970,906. Prior to evaporating the amorphous selenium on the substrate, a 0.5 micron layer of an epoxy phenolic barrier layer is formed over the aluminum by dip coating. Vacuum deposition is carried out at a vacuum of 106 Torr, while the substrate is maintained at a temperature . . .
~lZ6564 of about 50C during the vacuum deposition. The charge transport layer is prepared by dissolving 0.3 grams of Makrolon~ polycarbonate and 0.2 grams of the diamine of Example I in 3 milliliters of methylene chloride. A 25 micron thick layer of this solution is overcoated onto the amorphous 5 selenium surface. The resulting device is heated at 40C for 16 hours to remove volatiles.
The device is xerographically tested as follows: the device is corona charged to a negative potential of 1,2û0 volts and is subjected to a light flash of 4330 angstrom wavelength snd approximately 10 ergs/per 10 centimeter intensity. The duration of exposure was about 2 microseconds.
The device "instantly" (i.e. within the 5 millisecond response time of the recorder) discharged to 0 volts. This device was employed to make excellent reproductions on a Xerox Model D copier.
Example IIl N,N'-bis(3-methylphenyl~N,N'-diphenyl-[p-terphenyl]-4,4"-diam-ine was prepared by the process of Example I employing 10.98 grams of 3-methyl diphenylamine in place of the 3-methyl-4"-(1-butyl~ diphenylamine.
This compound was employed as the charge transport molecule in preparing an electrophotographic plate using a ratio of polycarbonate to diamine of 3:1 20 which is otherwise the same as that of Example II. The resulting device was tested as in the preceeding example and it exhibited the same immediate discharge characteristics.
The invention has been described in detail with particular reference to preferred embodiments thereof but it will be understood that 25 variations and modifications can be effected within the spirit and scope of the invention as described hereinabove and as defined in the appended claims.
. ' . -.
.
. ' ' . . ':
.
., .
~lZ6564 of about 50C during the vacuum deposition. The charge transport layer is prepared by dissolving 0.3 grams of Makrolon~ polycarbonate and 0.2 grams of the diamine of Example I in 3 milliliters of methylene chloride. A 25 micron thick layer of this solution is overcoated onto the amorphous 5 selenium surface. The resulting device is heated at 40C for 16 hours to remove volatiles.
The device is xerographically tested as follows: the device is corona charged to a negative potential of 1,2û0 volts and is subjected to a light flash of 4330 angstrom wavelength snd approximately 10 ergs/per 10 centimeter intensity. The duration of exposure was about 2 microseconds.
The device "instantly" (i.e. within the 5 millisecond response time of the recorder) discharged to 0 volts. This device was employed to make excellent reproductions on a Xerox Model D copier.
Example IIl N,N'-bis(3-methylphenyl~N,N'-diphenyl-[p-terphenyl]-4,4"-diam-ine was prepared by the process of Example I employing 10.98 grams of 3-methyl diphenylamine in place of the 3-methyl-4"-(1-butyl~ diphenylamine.
This compound was employed as the charge transport molecule in preparing an electrophotographic plate using a ratio of polycarbonate to diamine of 3:1 20 which is otherwise the same as that of Example II. The resulting device was tested as in the preceeding example and it exhibited the same immediate discharge characteristics.
The invention has been described in detail with particular reference to preferred embodiments thereof but it will be understood that 25 variations and modifications can be effected within the spirit and scope of the invention as described hereinabove and as defined in the appended claims.
. ' . -.
.
. ' ' . . ':
.
., .
Claims (9)
1. An imaging member comprising a charge generation layer comprising a layer of photoconductive material and a contiguous charge transport layer of a polycarbonate resin material having dispersed therein from about 25 to about 75 percent by weight of one or more diamine compound having the general formula:
wherein X1 and X2 are independently selected from the group consisting of a lower alkyl group having from 1 to about 4 carbon atoms, chlorine in the ortho, meta or para position, a para phenyl group and combinations thereof, said photoconductive layer exhibiting the capability of photogeneration of holes and injection of said holes and said charge transport layer being substantially nonabsorbing in the spectral region at which the photoconduc-tive layer generates and injects photogenerated holes but being capable of supporting the injection of photogenerated holes from said photoconductive layer and transporting said holes through said charge transport layer.
wherein X1 and X2 are independently selected from the group consisting of a lower alkyl group having from 1 to about 4 carbon atoms, chlorine in the ortho, meta or para position, a para phenyl group and combinations thereof, said photoconductive layer exhibiting the capability of photogeneration of holes and injection of said holes and said charge transport layer being substantially nonabsorbing in the spectral region at which the photoconduc-tive layer generates and injects photogenerated holes but being capable of supporting the injection of photogenerated holes from said photoconductive layer and transporting said holes through said charge transport layer.
2. The member of Claim 1 wherein the polycarbonate resin has a molecular weight of from about 20,000 to about 120,000.
3. The member of Claim 2 wherein the polycarbonate is poly(4,4"-isopropylidene-diphenylene carbonate).
4. The member according to Claim 3 wherein the polycarbonate has a molecular weight between from about 25,000 to about 45,000.
5. The member according to Claim 3 wherein the polycarbonate has a molecular weight of from about 50,000 to about 120,000.
6. The member of Claim 1 wherein the photoconductive material is selected from the group consisting of amorphous selenium, trigonal selenium, and selenium alloys selected from the group consisting of selenium-tellurium, selenium-tellurium-arsenic, selenium-arsenic and mix-tures thereof.
7. The member of Claim 5 wherein the photoconductive material is selected from the group consisting of amorphous selenium, trigonal selenium, and selenium alloys selected from the group consisting of selenium-tellurium, selenium-te11urium-arsenic, selenium-arsenic and mix-tures thereof.
8. The member of Claim 7 wherein the diamine compound is N,N'diphenyl-N,N'-bis(3-methylphenyl)[p-terphenyl]-4,4"-diamine.
9. The member of Claim 7 wherein the diamine compound is N,N'-bis(2-methylphenyl)N,N'-bis[4-(1-butyl)phenyl]-[p-terphenyl]-4,4"-dia-mine.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/097,024 US4273846A (en) | 1979-11-23 | 1979-11-23 | Imaging member having a charge transport layer of a terphenyl diamine and a polycarbonate resin |
US097,024 | 1979-11-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1126564A true CA1126564A (en) | 1982-06-29 |
Family
ID=22260391
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA363,619A Expired CA1126564A (en) | 1979-11-23 | 1980-10-30 | Imaging member having a charge transport layer of terphenyl diamine in a polycarbonate resin |
Country Status (5)
Country | Link |
---|---|
US (1) | US4273846A (en) |
EP (1) | EP0029703B1 (en) |
JP (1) | JPS56119132A (en) |
CA (1) | CA1126564A (en) |
DE (1) | DE3067194D1 (en) |
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US3953207A (en) * | 1974-10-25 | 1976-04-27 | Xerox Corporation | Composite layered photoreceptor |
US4078925A (en) * | 1976-11-01 | 1978-03-14 | Xerox Corporation | Composite layered photoreceptor |
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-
1979
- 1979-11-23 US US06/097,024 patent/US4273846A/en not_active Expired - Lifetime
-
1980
- 1980-10-30 CA CA363,619A patent/CA1126564A/en not_active Expired
- 1980-11-17 JP JP16182880A patent/JPS56119132A/en active Granted
- 1980-11-19 DE DE8080304139T patent/DE3067194D1/en not_active Expired
- 1980-11-19 EP EP80304139A patent/EP0029703B1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE3067194D1 (en) | 1984-04-26 |
JPS6355059B2 (en) | 1988-11-01 |
US4273846A (en) | 1981-06-16 |
JPS56119132A (en) | 1981-09-18 |
EP0029703A1 (en) | 1981-06-03 |
EP0029703B1 (en) | 1984-03-21 |
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