# US 9,040,215 B2 · Amine compound, electrophotographic photoconductor, image forming method, image forming apparatus, and process cartridge > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,215 B2 - Document ID: US9040215B2 - Status: Granted - Kind: B2 - Application number: 13/753,083 - Filed: 2013-01-29 - Published: 2013-08-08 - Granted: 2015-05-26 - Earliest claimed: 2012-02-03 - Assignees: Ricoh Company, Ltd. - Applicants: Tomoyuki Shimada; Masayoshi Nomura; Ryota Arai - Inventors: Tomoyuki Shimada; Masayoshi Nomura; Ryota Arai - Web page: https://patentgrep.com/patent/US9040215B2 ## CPC - G03G 15/751: {relating to drum (G03G15/757 takes precedence)} - C07C 211/54: having amino groups bound to two or three six-membered aromatic rings - G03G 5/06142: {arylamine} - G03G 5/06147: {alkenylarylamine} - G03G 2215/00957: Compositions - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract To provide an amine compound, represented by General Formula (I) below: [In General Formula (I), R1 and R2 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be identical or different; m and n are an integer of 1 or 0; Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group; Ar2 and Ar3 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; and Ar1 and Ar2 or Ar2 and Ar3 may bind to each other to form a substituted or unsubstituted heterocyclic group including a nitrogen atom.] ## Claims ### Claim 1 An electrophotographic photoconductor, comprising: an electrically conductive substrate; and a photoconductive layer on the electrically conductive substrate, wherein the photoconductive layer includes an amine compound represented by Formula (I) below: wherein in Formula (I), R1 and R2 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be identical or different; m and n are an integer of 1 or 0; Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group; Ar2 and Ar3 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; and Ar1 and Ar2 or Ar2 and Ar3 may bind to each other to form a substituted or unsubstituted heterocyclic group including a nitrogen atom. ### Claim 2 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein the photoconductive layer includes a charge transport material. ### Claim 3 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein the charge transport material is a stilbene compound represented by Formula (4) below, wherein in Formula (4), a represents an integer of 0 or 1; R3 represents a hydrogen atom, an alkyl group or a substituted or unsubstituted phenyl group; Ar4 represents a substituted or unsubstituted aromatic hydrocarbon group; R4 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group; A1 represents a 9-anthryl group, a substituted or unsubstituted carbazolyl group, Formula (5) below or Formula (6) below; wherein in Formula (5) or (6), R5 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or Formula (7) below; b represents an integer of 1 to 3, and when b is 2 or greater, R5 may be identical or different, wherein in Formula (7), R6 and R7 represent a substituted or unsubstituted aromatic hydrocarbon group, and R6 and R7 are identical or different. ### Claim 4 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein the charge transport material is an aminobiphenyl compound represented by Formula (8) below, wherein in Formula (8), R8, R10 and R11 represent a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group; R9 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom; c, d, e and f represent an integer of 1, 2, 3 or 4, and when each thereof is an integer of 2, 3 or 4, R8, R9, R10 or R11 above are identical or different. ### Claim 5 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein the charge transport material is a diolefin aromatic compound represented by Formula (9), A2-CH═CH—Ar5—CH═CH-A2 (9) wherein in Formula (9), Ar5 represents a substituted or unsubstituted aromatic hydrocarbon group; A2 represents Formula (10) below, wherein in Formula (10), Ar6 represents a substituted or unsubstituted aromatic hydrocarbon group; R12 and R13 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. ### Claim 6 (depends on 2) The electrophotographic photoconductor according to claim 2, wherein the charge transport material is a polymeric charge transport material. ### Claim 7 (depends on 6) The electrophotographic photoconductor according to claim 6, wherein the polymeric charge transport material is a compound represented by Formula (11) below, wherein in Formula (11), R14 and R15 represent a substituted or unsubstituted aromatic hydrocarbon group; Ar7, Ar8 and Ar9 represent identical or different aromatic hydrocarbon group; g and h represent compositions: 0.1≦g≦1; 0≦h≦0.9; i represents a number of repeating units and is an integer of 5 to 5,000; X represents an aliphatic divalent group, a cyclic aliphatic divalent group, or a divalent group represented by Formula (12) below, wherein in Formula (12), each of R101 and R102 independently represents a substituted or unsubstituted alkyl group, an aromatic hydrocarbon group, or a halogen atom; j and k represent an integer of 0 to 4; Y represents a single bond, a linear, branched or cyclic alkylene group having 1 to 12 carbon atoms; —O—, —S—, —SO—, —SO2—, —CO—, —CO—O—Z—O—CO— where Z represents an divalent aliphatic group, or Formula (13) below, where R101 and R102 are identical or different, respectively, wherein in Formula (13), l represents an integer of 1 to 20; m represents an integer of 1 to 2,000; R103 and R104 represent a substituted or unsubstituted alkyl group or aryl group, where R103 and R104 are identical or different, respectively. ### Claim 8 (depends on 6) The electrophotographic photoconductor according to claim 6, wherein the polymeric charge transport material is a compound represented by Formula (14) below, wherein in Formula (14), Ar10, Ar11, Ar12, Ar13 and Ar14 represent a substituted or unsubstituted aromatic hydrocarbon group; Z represents an aromatic hydrocarbon group or Ar15-Za-Ar15—, where Ar15 represents a substituted or unsubstituted aromatic hydrocarbon group, Za represents O, S or an alkylene group; R105 and R106 represent a linear or branched alkylene group; n represents 0 or 1; g and h represent compositions: 0.1≦g≦1; 0≦h≦0.9; i represents a number of repeating units and is an integer of 5 to 5,000; X represents an aliphatic divalent group, a cyclic aliphatic divalent group, or a divalent group represented by Formula (12) below, wherein in Formula (12), each of R101 and R102 independently represents a substituted or unsubstituted alkyl group, an aromatic hydrocarbon group, or a halogen atom; j and k represent an integer of 0 to 4; Y represents a single bond, a linear, branched or cyclic alkylene group having 1 to 12 carbon atoms; —O—, —S—, —SO—, —SO2—, —CO—, —CO—O—Z—O—CO— where Z represents an divalent aliphatic group, or Formula (13) below, where R101 and R102 are identical or different, respectively, wherein in Formula (13), l represents an integer of 1 to 20; m represents an integer of 1 to 2,000; R103 and R104 represent a substituted or unsubstituted alkyl group or aryl group, where R103 and R104 are identical or different, respectively. ### Claim 9 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein the electrophotographic photoconductor includes a protective layer on an outermost surface, and the protective layer includes the amine compound represented by Formula (I). ### Claim 10 (depends on 9) The electrophotographic photoconductor according to claim 9, wherein the protective layer includes a filler. ### Claim 11 (depends on 9) The electrophotographic photoconductor according to claim 9, wherein the protective layer includes a resin formed by curing a polymerizable monomer. ### Claim 12 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein the amine compound is an amine compound represented by Formula (1) below: wherein in Formula (1), R1 and R2 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be identical or different; Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group; R4 and R5 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; and Ar1 and R4 or R4 and R5 may bind to each other to form a substituted or unsubstituted heterocyclic group including a nitrogen atom. ### Claim 13 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein the amine compound is an amine compound represented by Formula (2) below: wherein in Formula (2), R1, R2 and R7 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be identical or different; R1 and R2 may bind to each other to form a substituted or unsubstituted heterocyclic group including a nitrogen atom; Ar1 and Ar6 represent a substituted or unsubstituted aromatic hydrocarbon group. ### Claim 14 (depends on 1) The electrophotographic photoconductor according to claim 1, wherein the amine compound is an amine compound represented by Formula (3) below: wherein in Formula (3), R1 and R2 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be identical or different; R1 and R2 may bind to each other to form a substituted or unsubstituted heterocyclic group including a nitrogen atom; Ar1, Ar8 and Ar9 represent a substituted or unsubstituted aromatic hydrocarbon group. ### Claim 15 An image forming apparatus, comprising: an electrophotographic photoconductor; a charging unit which charges a surface of the electrophotographic photoconductor; an exposure unit which exposes the charged surface of the electrophotographic photoconductor to form an electrostatic latent image; a developing unit which develops the electrostatic latent image using a toner to form a visible image; and a transfer unit which transfers the visible image to a recording medium, wherein the electrophotographic photoconductor is an electrophotographic photoconductor which comprises: an electrically conductive substrate; and a photoconductive layer on the electrically conductive substrate, wherein the photoconductive layer comprises an amine compound represented by Formula (I) below: wherein in Formula (I), R1 and R2 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be identical or different; m and n are an integer of 1 or 0; Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group; Ar2 and Ar3 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; and Ar1 and Ar2 or Ar2 and Ar3 may bind to each other to form a substituted or unsubstituted heterocyclic group including a nitrogen atom. ### Claim 16 (depends on 15) The image forming apparatus according to claim 15, wherein the exposure unit is any one of a laser diode and a light-emitting diode, and the electrostatic latent image is digitally written on the electrophotographic photoconductor using the exposure unit.