# US 4,397,931 A · Stabilized organic layered photoconductive device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,397,931 A - Document ID: US4397931A - Status: Granted - Kind: A - Application number: 06/383,672 - Filed: 1982-06-01 - Granted: 1983-08-09 - Earliest claimed: 1982-06-01 - Assignees: Xerox Corporation - Inventors: William W. Limburg; Dale S. Renfer; Damodar M. Pai - Web page: https://patentgrep.com/patent/US4397931A ## CPC - G03G 5/061443: {benzidine} - G03G 5/06142: {arylamine} - G03G 5/0618: {containing oxygen and nitrogen} - G03G 5/0629: {containing one hetero atom} - G03G 5/0631: {containing two hetero atoms} - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract This invention is generally directed to an organic layered photoresponsive device containing a charge transport layer comprised of a composition of the following: ##STR1## dispersed in a highly insulating and transparent organic resinous material, wherein x is selected from the group consisting of ortho (CH.sub.3), meta (CH.sub.3), para (CH.sub.3), ortho (Cl), meta (Cl), and para (Cl), and dispersed in said transport layer from about 0.1 weight percent to about 10 weight percent of an additive composition selected from the group consisting of ##STR2## wherein R and R.sub.1 are independently selected from the group consisting of ethylene groups containing from about 1 to about 6 carbon atoms such as methylene, ethylene, propylene, butylene and the like, and n is 0 or 1; ##STR3## wherein R.sub.2 and R.sub.3 are independently selected from alkyl groups containing from about 1 to about 6 carbon atoms, and R.sub.4 is selected from the group consisting of alkyl groups containing from about 1 to about 6 carbon atoms, CH.sub.2 OH, (CH.sub.3).sub.2 OH, and ##STR4## wherein R.sub.2 is an alkyl group; ##STR5## wherein R.sub.6 and R.sub.7 are alkyl groups; and ##STR6## wherein R.sub.8, R.sub.9, R.sub.10, and R.sub.11 are alkyl groups. ## Claims ### Claim 1 A stabilized organic layered photoresponsive device comprised of a substrate, a photogenerating layer and a charge transport layer in contact with the photogenerating layer, the charge transport layer being comprised of a composition of the following formula: ##STR14## dispersed in a highly insulating and transparent organic resinous material, wherein x is selected from the group consisting of ortho (CH.sub.3), meta (CH.sub.3), para (CH.sub.3), ortho (Cl), meta (Cl), and para (Cl), and dispersed in said transport layer from about 0.1 weight percent to about 10 weight percent of an additive composition selected from the group consisting of ##STR15## wherein R and R.sub.1 are independently selected from the group consisting of ethylene groups containing from about 1 to about 6 carbon atoms, and n is 0 or 1; ##STR16## wherein R.sub.2 and R.sub.3 are independently selected from alkyl groups containing from about 1 to about 6 carbon atoms, and R.sub.4 is selected from the group consisting of alkyl groups containing from about 1 to about 6 carbon atoms, CH.sub.2 OH, (CH.sub.3).sub.2 OH, and ##STR17## wherein R.sub.2 is an alkyl group; ##STR18## wherein R.sub.6 and R.sub.7 are alkyl groups; and ##STR19## wherein R.sub.8, R.sub.9, R.sub.10, and R.sub.11 are alkyl groups. ### Claim 2 (depends on 1) A device in accordance with claim 1 wherein the charge transport composition is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine. ### Claim 3 (depends on 1) A device in accordance with claim 1 wherein the resinous binder is a polycarbonate resin present in an amount of from about 25 percent by weight to about 90 percent by weight. ### Claim 4 (depends on 1) A device in accordance with claim 1 wherein the additive is tetrahydrofuran. ### Claim 5 (depends on 1) A device in accordance with claim 1 wherein the additive is 4-N,N-diethylcumidine. ### Claim 6 (depends on 1) A device in accordance with claim 1 wherein the additive is N,N-diethyl-p-toluidine. ### Claim 7 (depends on 1) A device in accordance with claim 1 wherein the additive is 4-diethylamino phenylcarbinol. ### Claim 8 (depends on 1) A device in accordance with claim 1 wherein the additive is N-ethyl-N(.beta.-hydroxyethyl)aniline. ### Claim 9 (depends on 1) A device in accordance with claim 1 wherein the additive is 1-phenyl-3-pyrazolidone. ### Claim 10 (depends on 1) A device in accordance with claim 1 wherein the additive is N,N-dimethyl-m-toluidine. ### Claim 11 (depends on 1) A device in accordance with claim 1 wherein the additive is N,N-dimethyl-p-toluidine. ### Claim 12 (depends on 1) A device in accordance with claim 1 wherein the additive is 3-N,N-diethyl propanolamine. ### Claim 13 (depends on 1) A device in accordance with claim 1 wherein the additive is tetramethylethylene diamine. ### Claim 14 (depends on 1) A device in accordance with claim 1 wherein the additive is tetrahydrofurfuryl oleate. ### Claim 15 (depends on 1) A device in accordance with claim 1 wherein the additive is tetrahydrofurfuryl alcohol. ### Claim 16 (depends on 1) A device in accordance with claim 1 wherrein the additive is 2-(4'-diethylaminophenyl)-1,3-diphenylimidazolidone. ### Claim 17 (depends on 1) An imaging member in accordance with claim 1 wherein the photogenerating layer is trigonal or vanadyl phthalocyanine, the substrate is aluminum and the charge transport layer is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-phenyl]-4,4'-diamine. ### Claim 18 (depends on 1) An organic layered photoconductive imaging device in accordance with claim 1 wherein the additive is tetrahydrofurane, 4-N,N-diethylcumidine, N,N-diethyl-p-toluidine, 4-diethyl amino phenylcarbinol, N-ethyl-N(.beta.-hydroxyethyl) aniline, 1-phenyl-3-pyrazolidone, N,N-dimethyl-m-toluidine, N,N-dimethyl-p-toluidine, 3-N,N-diethyl propanolamine, tetramethyl ethylene diamine, tetrahydrofurfuryl oleate, tetrahydrofurfuryl alcohol, or 2,-(4'-diethylaminephenyl)-1,3-diphenylimidazolidone.