Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus
An electrophotographic photosensitive member includes a support, a photosensitive layer, and a surface layer. The surface layer includes a cured product of a composition containing an organic salt having a polymerizable functional group, and at least one of a charge-transportable compound or electroconductive particles. The organic salt is formed of an organic cation and at least one of BF 4 − , PF 6 − , (CF 3 SO 2 ) 2 N − , CF 3 SO 3 − , (FSO 2 )N − , C 2 H 5 OSO 3 − , (CN) 2 N − , SCN − , CH 3 COO − , NO 3 − , Cl − , Br − or I − .
1. An electrophotographic photosensitive member, comprising:
a support; and
a surface layer, the surface layer comprises a cured product of a composition containing an organic salt having a polymerizable functional group and at least one member selected from the group consisting of a charge-transportable compound and an electroconductive particle, wherein
the organic salt is at least one compound selected from the group consisting of formulae (A)-(E)
where R a1 and R a3 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R a2 represents a hydrogen atom, a methyl group or an ethyl group,
Z a1 and Z a2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z a1 or Z a2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R b1 , R b3 and R b4 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R b2 represents a hydrogen atom, a methyl group or an ethyl group,
Z b1 , Z b2 and Z b3 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z b1 , Z b2 or Z b3 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R c1 and R c2 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z c1 and Z c2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group a thiol group, or an amino group, provided that at least one of Z c1 or Z c2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
n represents 1 or 2, and
R d1 and R d2 independently represent a single bond, or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R d3 and R d4 independently represent an alkyl group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z d1 and Z d2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z d1 or Z d2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R e1 and R e2 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R e3 and R e4 independently represent an alkyl group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z e1 and Z e2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z e1 or Z e2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group, and
X − represents BF 4 − , PF 6 − , (CF 3 SO 2 ) 2 N − , CF 3 SO 3 − , (FSO 2 )N − , C 2 H 5 OSO 3 − , (CN) 2 N − , SCN − , CH 3 COO − , NO 3 − , Cl − , Br − or I − .
2. The electrophotographic photosensitive member according to claim 1 , wherein the organic cation is at least member selected from the group consisting of an imidazolium, a pyridinium, a pyrrolidinium, a piperidinium, a tetraalkylammonium and a tetraalkylphosphonium.
3. The electrophotographic photosensitive member according to claim 1 , wherein the composition contains the charge-transportable compound, the charge-transportable compound comprising a charge-transporting monomer having a polymerizable functional group capable of reacting with the organic salt.
4. The electrophotographic photosensitive member according to claim 3 , wherein the charge-transporting monomer is represented by formula (1)
where R 1 and R 4 independently represent a single bond, an unsubstituted alkylene group having 3 or less carbon atoms or a phenylene group,
R 2 , R 3 , R 5 and R 6 independently represent a hydrogen atom, a methyl group, or an ethyl group, and
Z 1 and Z 2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z 1 or Z 2 represents an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group, or an amino group.
5. The electrophotographic photosensitive member according to claim 4 , wherein at least one of Z 1 or Z 2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group.
6. The electrophotographic photosensitive member according to claim 1 , wherein the composition contains the charge-transportable compound, and
a content ratio of the charge-transportable compound with respect to the organic salt in the composition is 10 to 1,000 mass %.
7. The electrophotographic photosensitive member according to claim 1 , wherein the composition contains the electroconductive particles, and
a content ratio of the electroconductive particles with respect to the organic salt in the composition is 10 to 1,000 mass %.
8. The electrophotographic photosensitive member according to claim 1 , wherein the composition contains titanium oxide electroconductive particles.
9. The electrophotographic photosensitive member according to claim 8 , wherein the titanium oxide particle contains niobium.
10. The electrophotographic photosensitive member according to claim 1 , wherein the composition contains the charge-transportable compound, and
the electrophotographic photosensitive member comprises the support, a charge-generating layer, a first charge-transporting layer and a second charge-transporting layer as the surface layer, in this order.
11. The electrophotographic photosensitive member according to claim 1 , wherein the composition contains the electroconductive particle, and
the electrophotographic photosensitive member comprises the support, a charge-generating layer, a charge-transporting layer and the surface layer, in this order.
12. A process cartridge comprising an electrophotographic photosensitive member and at least one unit selected from the group consisting of a charging unit, a developing unit and a cleaning unit,
the process cartridge integrally supporting the electrophotographic photosensitive member and the at least one unit, and being detachably attachable to a main body of an electrophotographic apparatus,
the electrophotographic photosensitive member comprising:
a support; and
a surface layer, the surface layer comprises a cured product of a composition containing an organic salt having a polymerizable functional group and at least one member selected from the group consisting of a charge-transportable compound and an electroconductive particle, wherein
the organic salt is at least one compound selected from the group consisting of formulae (A)-(E)
where R a1 and R a3 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R a2 represents a hydrogen atom, a methyl group or an ethyl group,
Z a1 and Z a2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z a1 or Z a2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R b1 , R b3 and R b4 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R b2 represents a hydrogen atom, a methyl group or an ethyl group,
Z b1 , Z b2 and Z b3 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z b1 , Z b2 or Z b3 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R c1 and R c2 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z c1 and Z c2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group a thiol group, or an amino group, provided that at least one of Z c1 or Z c2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
n represents 1 or 2, and
R d1 and R d2 independently represent a single bond, or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R d3 and R d4 independently represent an alkyl group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z d1 and Z d2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z d1 or Z d2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R e1 and R e2 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R e3 and R e4 independently represent an alkyl group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z e1 and Z e2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z e1 or Z e2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group, and
X − represents BF 4 − , PF 6 − , (CF 3 SO 2 ) 2 N − , CF 3 SO 3 − , (FSO 2 ) N − , C 2 H 5 OSO 3 − , (CN) 2 N − , SCN − , CH 3 COO − , NO 3 − , Cl − , Br − or I − .
13. An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging unit, an exposing unit, a developing unit and a transferring unit,
the electrophotographic photosensitive member comprising:
a support; and
a surface layer, the surface layer comprises a cured product of a composition containing an organic salt having a polymerizable functional group and at least one member selected from the group consisting of a charge-transportable compound and an electroconductive particle, wherein
the organic salt is at least one compound selected from the group consisting of formulae (A)-(E)
where R a1 and R a3 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R a2 represents a hydrogen atom, a methyl group or an ethyl group,
Z a1 and Z a2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z a1 or Z a2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R b1 , R b3 and R b4 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R b2 represents a hydrogen atom, a methyl group or an ethyl group,
Z b1 , Z b2 and Z b3 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z b1 , Z b2 or Z b3 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R c1 and R c2 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z c1 and Z c2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group a thiol group, or an amino group, provided that at least one of Z c1 or Z c2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
n represents 1 or 2, and
R d1 and R d2 independently represent a single bond, or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R d3 and R d4 independently represent an alkyl group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z d1 and Z d2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z d1 or Z d2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group,
R e1 and R e2 independently represent a single bond or an alkylene group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
R e3 and R e4 independently represent an alkyl group having 8 or less carbon atoms that may have a hydroxy group as a substituent,
Z e1 and Z e2 independently represent a hydrogen atom, an acryloyloxy group, a methacryloyloxy group, a vinyl group, a hydroxy group, a carboxy group, a thiol group or an amino group, provided that at least one of Z e1 or Z e2 represents an acryloyloxy group, a methacryloyloxy group or a vinyl group, and X − represents BF 4 − , PF 6 − , (CF 3 SO 2 ) 2 N − , CF 3 SO 3 − , (FSO 2 )N − , C 2 H 5 OSO 3 − , (CN) 2 N − , SCN − , CH 3 COO − , NO 3 − , Cl − , Br − or I −.