Electrophotographic photosensitive member
AssigneeCanon Kabushiki Kaisha
InventorsToshihiro Kikuchi, Akio Maruyama, Noriko Ohtani, Shin Nagahara, Hisami Tanaka, Teigo Sakakibara, Takakazu Tanaka
Life of this patent
Estimating the term…
Abstract
An electrophotographic photosensitive member has an electroconductive support and a photosensitive layer thereon which contains a compound of Formula 3, 5-11, 13 or 14 as follows: ##STR1##
Claims23
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound selected from the group consisting of a compound represented by the following formulas 3, 5-11, 13 and 14 as follows:
- ##STR2168## wherein each of R.sub.3-1, R.sub.3-2, R.sub.3-3 and R.sub.3-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2169## each of at least two of R.sub.3-1 to R.sub.3-4 is ##STR2170## each of R.sub.3-5 and R.sub.3-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.3-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.3-6 and R.sub.3-7, may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, ##STR2171## wherein each of R.sub.5-1, R.sub.5-2, R.sub.5-3, R.sub.5-4, R.sub.5-5, and R.sub.5-6, is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2172## each of at least two of R.sub.5-1 to R.sub.5-6 are
- --(CH.dbd.CH).sub.p --NO.sub.2, --(CH.dbd.CH).sub.q --R.sub.5-7,
- or ##STR2173## each of R.sub.5-7 and R.sub.5-8 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.5-9 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.5-8 and R.sub.5-9, may be mutually bonded to form a ring directly or with the interposition of an saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, ##STR2174## wherein each of R.sub.6-1, R.sub.6-2, R.sub.6-3, R.sub.6-4, R.sub.6-5 and R.sub.6-6 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2175## each of at least two of R.sub.6-1 to R.sub.6-6 is ##STR2176## each of R.sub.6-7 and R.sub.6-8 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.6-9 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.6-8 and R.sub.6-9 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, ##STR2177## wherein each of R.sub.7-1, R.sub.7-2, R.sub.7-3, and R.sub.7-4 is a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, or an aromatic ring group, ##STR2178## each of at least two of R.sub.7-1 to R.sub.7-4 is ##STR2179## each of R.sub.7-5 and R.sub.7-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.7-7 is an alkyl group, an aralkyl group, an aromatic ring group, or a heterocyclic ring group;
- each of p and q is an integer of 0, 1, or 2;
- and r is an integer of 0 or 1;
- R.sub.7-6 and R.sub.7-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, ##STR2180## wherein each of R.sub.8-1, R.sub.8-2, R.sub.8-3 and R.sub.8-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2181## each of at least two of R.sub.8-1 to R.sub.8-4 is ##STR2182## each of R.sub.8-5 and R.sub.8-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.8-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is a integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.8-6 and R.sub.8-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, ##STR2183## wherein each of R.sub.9-1, R.sub.9-2, R.sub.9-3 and R.sub.9-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2184## each of at least two of R.sub.9-1 to R.sub.9-4 is ##STR2185## each of R.sub.9-5 and R.sub.9-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.9-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic ring group;
- each of i, f and g is an integer of 1 or 2;
- and h is an integer of 0 or 1;
- R.sub.9-6 and R.sub.9-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atoms or a sulfur atom, ##STR2186## wherein each of R.sub.10-1, R.sub.10-2, R.sub.10-3 and R.sub.10-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2187## each of at least two of R.sub.10-1 to R.sub.10-4 is ##STR2188## each of R.sub.10-5 and R.sub.10-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.10-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic ring group;
- each of i, f and g is an integer of 1 or 2;
- and h is an integer of 0 or 1;
- R.sub.10-6 and R.sub.10-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, ##STR2189## wherein each or R.sub.11-1 and R.sub.11-2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2190## at least either or R.sub.11-1 and ##STR2191## each of R.sub.11-5 and R.sub.11-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.11-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- R.sub.11-6 and R.sub.11-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom;
- and of R.sub.11-3 and R.sub.11-4 is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic ring group, a nitro group or a cyano group;
- each of p and g is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1, ##STR2192## wherein each of R.sub.13-1, R.sub.13-2, R.sub.13-3 and R.sub.13-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic ring group, ##STR2193## each of at least two of R.sub.13-1 to R.sub.13-4 is ##STR2194## each of R.sub.13-5 and R.sub.13-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.13-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.13-6 and R.sub.13-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom, and ##STR2195## wherein each of R.sub.14-1, R.sub.14-2, R.sub.14-3 and R.sub.14-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2196## each of at least two of R.sub.14-1 to R.sub.14-4 is ##STR2197## each of R.sub.14-5 and R.sub.14-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.14-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of k, f and g is an integer of 1 or 2;
- and h is an integer or 0 of 1;
- R.sub.14-6 and R.sub.14-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (3) ##STR2198## wherein each of R.sub.3-1, R.sub.3-2, R.sub.3-3 and R.sub.3-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2199## each of at least two of R.sub.3-1 to R.sub.3-4 is ##STR2200## each of R.sub.3-5 and R.sub.3-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.3-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.3-6 and R.sub.3-7, may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (5) ##STR2201## wherein each of R.sub.5-1, R.sub.5-2, R.sub.5-3, R.sub.5-4, R.sub.5-5, and R.sub.5-6, is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2202## each of at least two of R.sub.5-1 to R.sub.5-6 are ##STR2203## each of R.sub.5-7 and R.sub.5-8 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.5-9 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.5-8 and R.sub.5-9, may be mutually bonded to form a ring directly or with the interposition of an saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (6) ##STR2204## wherein each of R.sub.6-1, R.sub.6-2, R.sub.6-3, R.sub.6-4, R.sub.6-5 and R.sub.6-6 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2205## each of at least two of R.sub.6-1 to R.sub.6-6 is ##STR2206## each of R.sub.6-7 and R.sub.6-8 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.6-9 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.6-8 and R.sub.6-9 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (7) ##STR2207## wherein each of R.sub.7-1, R.sub.7-2, R.sub.7-3, and R.sub.7-4 is a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, or an aromatic ring group, --(CH.dbd.CH).sub.p --NO.sub.2, (CH.dbd.CH).sub.q --R.sub.7-5 or ##STR2208## each of at least two of R.sub.7-1 to R.sub.7-4 is ##STR2209## each of R.sub.7-5 and R.sub.7-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.7-7 is an alkyl group, an aralkyl group, an aromatic ring group, or a heterocyclic ring group;
- each of p and q is an integer of 0, 1, or 2;
- and r is an integer of 0 or 1;
- R.sub.7-6 and R.sub.7-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (8) ##STR2210## wherein each of R.sub.8-1, R.sub.8-2, R.sub.8-3 and R.sub.8-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2211## each of at least two of R.sub.8-1 to R.sub.8-4 is ##STR2212## each of R.sub.8-5 and R.sub.8-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.8-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is a integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.8-6 and R.sub.8-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (9) ##STR2213## wherein each of R.sub.9-1, R.sub.9-2, R.sub.9-3 and R.sub.9-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2214## each of at least two of R.sub.9-1 to R.sub.9-4 is ##STR2215## each of R.sub.9-5 and R.sub.9-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.9-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic ring group;
- each of i, f and g is an integer of 1 or 2;
- and h is an integer of 0 or 1;
- R.sub.9-6 and R.sub.9-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atoms or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (10) ##STR2216## wherein each of R.sub.10-1, R.sub.10-2, R.sub.10-3 and R.sub.10-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2217## each of R.sub.10-5 and R.sub.10-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.10-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heterocyclic ring group;
- each of i, f and g is an integer of 1 or 2;
- and h is an integer of 0 or 1;
- R.sub.10-6 and R.sub.10-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (11) ##STR2218## wherein each or R.sub.11-1 and R.sub.11-2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2219## each of R.sub.11-5 and R.sub.11-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.11-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- R.sub.11-6 and R.sub.11-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom;
- and of R.sub.11-3 and R.sub.11-4 is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic ring group, a nitro group or a cyano group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer or 0 or 1.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (13) ##STR2220## wherein each of R.sub.13-1, R.sub.13-2, R.sub.13-3 and R.sub.13-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic ring group, ##STR2221## each of at least two of R.sub.13-1 to R.sub.13-4 is ##STR2222## each of R.sub.13-5 and R.sub.13-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.13-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of p and q is an integer of 0, 1 or 2;
- and r is an integer of 0 or 1;
- R.sub.13-6 and R.sub.13-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
An electrophotographic photosensitive member comprising an electroconductive support and a photosensitive layer on said electroconductive support, said photosensitive layer containing a compound represented by the formula (11) ##STR2223## wherein each of R.sub.14-1, R.sub.14-2, R.sub.14-3 and R.sub.14-4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic ring group, ##STR2224## each of at least two of R.sub.14-1 to R.sub.14-4 is ##STR2225## each of R.sub.14-5 and R.sub.14-6 is an aromatic ring group having a nitro group or a heterocyclic ring group having the nitro group;
- R.sub.14-7 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic ring group;
- each of k, f and g is an integer of 1 or 2;
- and h is an integer of 0 or 1;
- R.sub.14-6 and R.sub.14-7 may be mutually bonded to form a ring directly or with the interposition of a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom.
Dependencies are inferred from the claim text.