Electrophotographic photoreceptor, and image forming method, image forming apparatus and process cartridge therefor using the photoreceptor

An electrophotographic photoreceptor comprising:

• an electroconductive substrate;
• and
• a photosensitive layer located overlying the electroconductive substrate,
• wherein the photosensitive layer compnses an amino compound having at least one aromatic group substituted with a dialkylamine,
• wherein the amino compound is at least one selected from the group consisting of the following formulae (1) to (22):
• wherein R1 and R2 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• n1 represents an integer of from 1 to 4;
• and Ar represents a substituted or unsubstituted aromatic ring group;
• wherein R21 and R22 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• l2, m2 and n2 independently represent 0 or an integer of from 1 to 3, wherein l2, m2 and n2 are not 0 at the same time;
• Ar21, A22 and Ar23 independently represent a substituted or unsubstituted aromatic ring group;
• and each of combinations of Ar21 and Ar22, Ar22 and Ar23, and Ar23 and Ar21 optionally shares bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• wherein R31 and R32 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• k3, l3, m3 and n3 independently represent 0 or an integer of from 1 to 3, wherein k3, l3, m3 and n3 are not 0 at the same time;
• Ar31, Ar32, Ar33 and Ar34 independently represent a substituted or unsubstituted aromatic ring group;
• and each of combinations of Ar31 and Ar32, Ar31 and Ar34, and Ar33 and Ar34 shares bond connectivity to form a ring;
• wherein R41 and R42 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• k4, l4, m4 and n4 independently represent 0 or an integer of from 1 to 3, wherein k4, l4, m4 and n4 are not 0 at the same time;
• Ar41, Ar42, Ar43 and Ar44 independently represent a substituted or unsubstituted aromatic ring group;
• and each of combinations of Ar41 and Ar42, Ar41 and Ar43, and Ar43 and Ar44 optionally shares bond connectivity to form a ring;
• wherein R51 and R52 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• k5, l5, m5 and n5 independently represent 0 or an integer of from 1 to 3, wherein k5, l5, m5 and n5 are not 0 at the same time;
• Ar51, Ar52, Ar53 and Ar54 independently represent a substituted or unsubstituted aromatic ring group;
• each of combinations of Ar51 and Ar52, Ar51 and Ar53, and Ar51 and Ar54 optionally shares bond connectivity to form a ring;
• and X represents a methylene group, a cyclohexylidine group, an oxygen atom or a sulfur atom;
• wherein R61 and R62 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a ring;
• l6 and m6 independently represent 0 or an integer of from 1 to 3, wherein 16 and m6 are not 0 at the same time;
• Ar61, Ar62 and Ar63 independently represent a substituted or unsubstituted aromatic ring group;
• each of combinations of Ar61 and Ar62 and Ar61 and Ar63 optionally shares bond connectivity to form a ring;
• and n6 represents an integer of from 1 to 4;
• wherein R71 and R72 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• m7 and n7 independently represent 0 or an integer of from 1 to 3, wherein m7 and n7 are not 0 at the same time;
• R73 and R74 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 11 carbon atoms and a substituted or unsubstituted aromatic ring group;
• and Ar71 and Ar72 independently represent a substituted or unsubstituted aromatic ring group, wherein one of Ar71, Ar72, R73 and R74 is an aromatic heterocyclic group;
• wherein R81 and R82 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• m8 and n8 independently represent 0 or an integer of from 1 to 3, wherein m8 and n8 are not 0 at the same time;
• R83 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 11 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar81, Ar82, Ar83, Ar84 and Ar85 independently represent a substituted or unsubstituted aromatic ring group;
• and Ar81 and Ar82 or Ar81 and Ar83 optionally form a heterocyclic group including the nitrogen atom to which they are attached;
• wherein R91 and R92 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• m9 and n9 independently represent 0 or an integer of from 1 to 3, wherein m and n are not 0 at the same time;
• Ar91, Ar92, Ar93, Ar94 and Ar95 independently represent a substituted or unsubstituted aromatic ring group;
• and Ar91 and Ar92 or Ar91 and Ar93 optionally form a heterocyclic group including the nitrogen atom to which they are attached;
• wherein R101 and R102 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• n10 represents an integer of from 1 to 3;
• Ar101, Ar102, Ar103 and Ar104 independently represent a substituted or unsubstituted aromatic ring group;
• and Ar101 and Ar102 or Ar101 and Ar103 optionally form a heterocyclic group including the nitrogen atom to which they are attached;
• wherein R111 and R112 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• l11 represents an integer of from 1 to 3;
• Ar111 and Ar112 independently represent a substituted or unsubstituted aromatic ring group;
• R113 and R114 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic ring group or a group having the following formula:
• wherein R111 and R112 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• m11 and n11 independently represent 0 or an integer of from 1 to 3;
• and R115 and R116 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group, and wherein each of combinations of R113 and R114, R115 and R116, and Ar111 and Ar112 optionally shares bond connectivity to form a ring;
• wherein R121 and R122 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• l12 represents an integer of from 1 to 3;
• Ar121 and Ar122 independently represent a substituted or unsubstituted aromatic ring group;
• R123 and R124 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic ring group or a group having the following formula;
• wherein R121 and R122 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• R123 and R124 are not hydrogen atoms at the same time;
• m12 and n12 independently represent 0 or an integer of from 1 to 3;
• and R125 and R126 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group, and wherein each of combinations of R123 and R124, R125 and R126, and Ar121 and Ar122 optionally shares bond connectivity to form a ring;
• wherein R131 and R132 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• R133 and R134 independently represent a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• R135, R136 and R137 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar131 and Ar132 independently represent a substituted or unsubstituted aromatic ring group;
• R133 and R134 or Ar132 and R134 optionally form a heterocyclic group including the nitrogen atom to which they are attached;
• Ar131 and R135 optionally form a ring;
• l13 represents an integer of from 1 to 3;
• m13 represents 0 or an integer of from 1 to 3;
• and n 13 represents 0 or 1;
• wherein R141 and R142 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• R143 and R144 independently represent a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• R145, R146 and R147 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstiluted aromatic ring group;
• Ar141 and Ar142 independently represent a substituted or unsubstituted aromatic ring group;
• R143 and R144 or Ar142 and R144 optionally form a heterocyclic group including the nitrogen atom to which they are attached;
• Ar141 and R145 optionally form a ring;
• l14 represents an integer of from 1 to 3;
• m14 represents 0 or an integer of from 1 to 3;
• and n14 represents 0 or 1;
• wherein R151 and R152 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• l15 and m15 independently represent 0 or an integer of from 1 to 3, wherein l15 and m15 are not 0 at the same time;
• R153 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• R154 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar151 and Ar152 independently represent a substituted or unsubstituted aromatic ring group;
• Ar151 and R154, Ar152 and R153 or Ar152 and another Ar152 optionally form a ring;
• and n15 represents 0 or 1;
• wherein R161 and R162 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• l16 and m16 independently represent 0 or an integer of from 1 to 3, wherein l16 and m16 are not Oat the same time;
• R163 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• R164 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar161 and Ar162 independently represent a substituted or unsubstituted aromatic ring group;
• Ar161 and R164, Ar162 and R163 or Ar162 and another Ar162 optionally form a ring;
• and n16 represents 0 or 1;
• wherein R171 and R172 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• k17, l17 and m17 independently represent 0 or an integer of from 1 to 3, wherein k17, l17 and m17 are not Oat the same time;
• R173 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar171 and Ar172 independently represent a substituted or unsubstituted aromatic ring group;
• Ar171 and R174, Ar172 and R173 or Ar172 and another Ar172 optionally form a ring;
• and n17 represents 0 or 1;
• wherein R181 and R182 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• k18, l18 and m18 independently represent 0 or an integer of from 1 to 3, wherein k18, l18 and m18 are not 0 at the same time;
• R183 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar181 and Ar182 represent a substituted or unsubstituted aromatic ring group;
• Ar181 and R184, Ar182 and R183 or Ar182 and another Ar182 optionally form a ring;
• and n18 represents 0 or 1;
• wherein R191 and R192 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• R193 and R194 independently represent a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• R195 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar191 and Ar192 independently represent a substituted or unsubstituteci aromatic group;
• R193 and R194 or Ar191 and R194 optionally form a heterocyclic group including the nitrogen atom to which they are attached ;
• k19, l19 and m19 independently represent 0 or an integer of from 1 to 3;
• n19 represents 1 or 2;
• and R193 and R194 independently represent an alkyl group having 1 to 4 carbon atoms when k19, l19 and m19 are 0 at the same time, and R193 and R194 optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• wherein R201 and R202 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• R203 and R204 independently represent a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• R205 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• Ar201 and Ar202 independently represent a substituted or unsubstituted aromatic ring group;
• R203 and R204 or Ar201 and R204 optionally form a heterocyclic group including the nitrogen atom to which they are attached;
• m20 represents 0 or an integer of from 1 to 4;
• n20 represents 1 or 2;
• and R203 and R204 independently represent an alkyl group having 1 to 4 carbon atoms when m20 is 0, and R203 and R204 optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• wherein R211 and R212 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• Ar represents a substituted or unsubstituted aromatic ring group;
• R213 and R214 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• and l21, m21 and n21 independently represent 0 or an integer of from 1 to 3, and are not 0 at the same time;
• wherein R221 and R222 independently represent an alkyl group having 1 to 4 carbon atoms and optionally share bond connectivity to form a heterocyclic group including the nitrogen atom to which they are attached;
• Ar221, Ar222 and Ar223 independently represent a substituted or unsubstituted aromatic ring group;
• R223 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aromatic ring group;
• l22 and m22 independently represent 0 or an integer of from 1 to 3, and are not 0 at the same time;
• and n22 represents an integer of from 1 to 3.