# US 7,745,081 B2 · Diphenyl amine derivative, production method therefor and electrophotographic photoconductor > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,745,081 B2 - Document ID: US7745081B2 - Status: Granted - Kind: B2 - Application number: 11/796,018 - Filed: 2007-04-26 - Published: 2007-11-29 - Granted: 2010-06-29 - Earliest claimed: 2006-05-25 - Assignees: Kyocera Mita Corporation - Inventors: Hideki Okada - Web page: https://patentgrep.com/patent/US7745081B2 ## CPC - C07C 211/60: containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems - G03G 5/06147: {alkenylarylamine} - G03G 5/061473: {plural alkenyl groups linked directly to the same aryl group} - C07C 2602/08: the other ring being five-membered, e.g. indane - C07C 2602/10: the other ring being six-membered, e.g. tetraline - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract The present invention provides a diphenyl amine derivative having the excellent solubility to a solvent and compatibility to a binding resin, an efficient production method therefor, and an electrophotographic photoconductor having the excellent sensitivity, capable of effectively preventing generation of the black dots. A diphenyl amine derivative represented by the following general formula (1) is used: (In the general formula (1), R1 to R12 each are a hydrogen atom, an alkyl group which may have a substituent, or the like, Z is a ring structure linked with a benzene ring, which is a 4 to 8-membered ring including a hydrogen atom, a nitrogen atom, an oxygen atom, a carbon atom or a sulfur atom, m1, m2, n1, n2 each are 0 or 1, m1+n1 is 1 or 2, and m2+n2 is 1 or 2.) ## Claims ### Claim 1 A diphenyl amine derivative represented by the following general formula (1): (In the general formula (1), R1 to R12 each are a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, a phenoxy group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, Z is a ring structure linked with a benzene ring, which is a 4 to 8-membered ring including a hydrogen atom, a nitrogen atom, an oxygen atom, a carbon atom or a sulfur atom, m1, m2, n1, n2 each are 0 or 1, m1+n1 is 1 or 2, and m2+n2 is 1 or 2), however neither m1+n1 nor m2+n2 become 1 at the same time, wherein a ring structure including a benzene ring in the diphenyl amine derivative represented by the general formula (1) is a structure represented by the following formula (2-1) or (2-2): ### Claim 2 (depends on 1) The diphenyl amine derivative according to claim 1, wherein when the ring structure including a benzene ring is represented by the formula (2-1), a nitrogen atom in the diphenyl amine derivative represented by the general formula (1) is bonded with the 5th or 6th place of the ring structure including a benzene ring, and when the ring structure including a benzene ring is represented by the formula (2-2), a nitrogen atom in the diphenyl amine derivative represented by the general formula (1) is bonded with the 4th or 5th place of the ring structure including a benzene ring. ### Claim 3 (depends on 1) The diphenyl amine derivative according to claim 1, wherein R1 to R3, R6, R7 to R9 and R12 in the general formula (I) are a hydrogen atom. ### Claim 4 (depends on 1) A production method for the diphenyl amine derivative according to claim 1, comprising the following steps (A) to (B): (A) a step of obtaining a compound represented by the following general formula (5) by reacting a compound represented by the following general formula (3) with a compound represented by the general formula (4a); and (B) a step of obtaining a diphenyl amine derivative represented by the general formula (1) by reacting the obtained compound represented by the general formula (5) with a compound represented by the following general formula (4b): (In the general formula (3), Z is a ring structure linked to a benzene ring, which is a 4 to 8-membered ring including a hydrogen atom, a nitrogen atom, an oxygen atom, a carbon atom or a sulfur atom); (In the general formula (4a), R1 to R6 each are a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, a phenoxy group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, X1 is a halogen atom, m1, n1 are each 0 or 1, and m1+n1 is 1 or 2); (In the general formula (4b), R7 to R12 each are a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, a phenoxy group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, X2 is a halogen atom, m2, n2 are each 0 or 1, and m2+n2 is 1 or 2); and (In the general formula (5), R1 to R6 each are a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, a phenoxy group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, Z is a ring structure linked to a benzene ring, which is a 4 to 8-membered ring including a hydrogen atom, a nitrogen atom, an oxygen atom, a carbon atom or a sulfur atom, m1, n1 are each 0 or 1, and m1+n1 is 1 or 2.) ### Claim 5 (depends on 4) The production method for a diphenyl amine derivative according to claim 4, wherein a palladium compound is used as a catalyst in steps (A) and (B), or in either of steps. ### Claim 6 (depends on 4) The production method for a diphenyl amine derivative according to claim 4, wherein steps (A) and (B), or either of the steps are carried out in the presence of a base. ### Claim 7 (depends on 1) An electrophotographic photoconductor comprising a photoconductor layer provided on a conductive base member, wherein the photoconductor layer contains the diphenyl amine derivative according to claim 1. ### Claim 8 (depends on 7) The electrophotographic photoconductor according to claim 7, wherein the photoconductor layer is a monolayer type photoconductor layer and the content of the diphenyl amine derivative is a value in a range of 20 to 500 parts by weight with respect to 100 parts by weight of the binding resin of the photoconductor layer. ### Claim 9 (depends on 7) The electrophotographic photoconductor according to claim 7, wherein the photoconductor layer is a multilayer type photoconductor layer and the content of the diphenyl amine derivative is a value in a range of 10 to 500 parts by weight with respect to 100 parts by weight of the binding resin of the charge transfer layer included in the photoconductor layer.