# US 5,700,614 A · cyclopentadiene derivative compounds and electrophotographic photoconductor comprising one cyclopentadiene derivative compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,700,614 A - Document ID: US5700614A - Status: Granted - Kind: A - Application number: 08/398,944 - Filed: 1995-03-02 - Granted: 1997-12-23 - Earliest claimed: 1994-03-03 - Assignees: Ricoh Company, Ltd. - Inventors: Megumi Kawahara; Ikuko Yamada; Masayuki Shoshi; Akio Kojima - Web page: https://patentgrep.com/patent/US5700614A ## CPC - C07C 251/20: having carbon atoms of imino groups being part of rings other than six-membered aromatic rings - C07C 49/683: having unsaturation outside the aromatic rings - C07C 49/753: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups - C07C 69/618: having unsaturation outside the six-membered aromatic ring - C07C 69/738: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} - C07C 255/34: with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains - C07C 255/37: the carbon skeleton being further substituted by etherified hydroxy groups - C07C 255/41: the carbon skeleton being further substituted by carboxyl groups, other than cyano groups - C07D 317/48: Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring - G03G 5/0607: {containing at least one non-six-membered ring} - G03G 5/0609: {containing oxygen} - G03G 5/0612: {containing nitrogen} - G03G 5/0618: {containing oxygen and nitrogen} - C07C 2602/08: the other ring being five-membered, e.g. indane - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract Cyclopentadiene derivative compounds, and an electrophotographic photoconductor comprising one cyclopentadiene derivative compound are disclosed. The cyclopentadiene derivative compounds are useful for use in a photoconductive layer, and readily soluble in a binder resin. The electrophotographic photoconductor can be prepared by using a simple, effective production method. The electrophotographic photoconductor comprising one cyclopentadiene derivative compound provides a good light sensitivity and high durability. ## Claims ### Claim 1 An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon comprising at least one cyclopentadiene derivative compound represented by a formula: ##STR477## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or an alkyl group which may have a substituent, wherein X represents: a substitution group of a formula .dbd.C--›A!›B! wherein A and B independently represent a halogen atom, a cyano group, an aromatic group which may have a substituent, or a group --COOR.sub.6 wherein R.sub.6 represents an alkyl group which may have a substituent, or an aromatic group which may have a substituent; or a substitution group of a formula .dbd.N--R.sub.5 where R.sub.5 represents a cyano group, an alkyl group which may have a substituent, or an aromatic group which may have a substituent. ### Claim 2 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein said photoconductive layer is a single layer in which a charge generating material and a charge transporting material coexist, said charge transporting material comprising said cyclopentadiene derivative compound. ### Claim 3 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein the substituent of said alkyl group R.sub.1 to R.sub.6 is halogen or phenyl, the substituent of said aromatic group R.sub.5, R.sub.6, A and B is chloro, bromo, methyl, ethyl, isopropyl, t-butyl, n-butyl, nitro, cyano, methoxyl, ethoxyl, acetoxyl, methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, methylcarbonyl, ethylcarbonyl, N,N-dimethylamino, benzoxyamino, N,N-dimethylamido, methylthioxy, trifluoromethyl, or phenyl. ### Claim 4 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein said alkyl group R.sub.1 to R.sub.6 which may have a substituent is methyl, ethyl, isopropyl, t-butyl, n-butyl, hexyl, octyl, cyclohexyl, cyclopentyl, trifluoromethyl, chloromethyl, bromoethyl, fluoropropyl or benzyl. ### Claim 5 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein said alkyl group R.sub.1 to R.sub.6 and aromatic group R.sub.5, R.sub.6, A and B are unsubstituted. ### Claim 6 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein said photoconductive layer has a laminated structure including a charge generating layer and a charge transporting layer, said charge transporting layer comprising said cyclopentadiene derivative compound. ### Claim 7 (depends on 6) The electrophotographic photoconductor according to claim 6, wherein the substituent of said alkyl group R.sub.1 to R.sub.6 is halogen or phenyl, the substituent of said aromatic group R.sub.5, R.sub.6, A and B is chloro, bromo, methyl, ethyl, isopropyl, t-butyl, n-butyl, nitro, cyano, methoxyl, ethoxyl, acetoxyl, methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, methylcarbonyl, ethylcarbonyl, N,N-dimethylamino, benzoxyamino, N,N-dimethylamido, methylthioxy, trifluoromethyl, or phenyl. ### Claim 8 (depends on 6) The electrophotographic photoconductor according to claim 6, wherein said alkyl group R.sub.1 to R.sub.6 which may have a substituent is methyl, ethyl, isopropyl, t-butyl, n-butyl, hexyl, octyl, cyclohexyl, cyclopentyl, trifluoromethyl, chloromethyl, bromoethyl, fluoropropyl or benzyl. ### Claim 9 (depends on 6) The electrophotographic photoconductor according to claim 6, wherein said alkyl group R.sub.1 to R.sub.6 and aromatic group R.sub.5, R.sub.6, A and B are unsubstituted. ### Claim 10 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein the substituent of said alkyl group of R.sub.1 to R.sub.6 is halogen or phenyl, the substituent of said aromatic group R.sub.5, R.sub.6, A and B is chloro, bromo, methyl, ethyl, isopropyl, t-butyl, n-butyl, nitro, cyano, methoxyl, ethoxyl, acetoxyl, methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, methylcarbonyl, ethylcarbonyl, N,N-dimethylamino, benzoxyamino, N,N-dimethylamido, methylthioxy, trifluoromethyl, or phenyl. ### Claim 11 (depends on 10) The electrophotographic photoconductor according to claim 10, wherein said alkyl group R.sub.1 to R.sub.6 which may have a substituent is methyl, ethyl, isopropyl, t-butyl, hexyl, octyl, cyclohexyl, cyclopentyl, trifluoromethyl, chloromethyl, bromoethyl, fluoropropyl or benzyl. ### Claim 12 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein said alkyl group R.sub.1 to R.sub.6 and aromatic group R.sub.5, R.sub.6, A and B are unsubstituted.