Electrophotographic member, process cartridge, and electrophotographic apparatus
Provided is an electrophotographic member which hardly undergoes deformation even when subjected to a load over a long period of time under a high-temperature and high-humidity environment and thus can stably form a high-quality electrophotographic image. The electrophotographic member includes: an electroconductive substrate; and an electroconductive resin layer on the substrate, in which the resin layer contains a cation having a specific structure and a specific anion.
1. An electrophotographic member, comprising:
an electroconductive substrate; and
an electroconductive resin layer on the substrate, wherein
the resin layer comprises a mixture of (i) a binder resin, (ii) an anion comprising at least one of a fluoroalkylsulfonylimide anion or a fluorosulfonylimide anion, and (iii) a cation selected from the group consisting of formulae (1) to (6)
A11-R101- A12 (1)
where A11 and A12 independently represent any of formulae (A101) to (A106), and R101 represents a linking group having a straight chain moiety of 4 or more carbon atoms, the linking group making a distance corresponding to a straight chain of 4 or more carbon atoms between A11 and A12;
where A13 and A14 independently represent any of formulae (A101) to (A106), R102 and R103 independently represent a divalent hydrocarbon group having 1 to 4 carbon atoms, R104 represents a monovalent hydrocarbon group having 1 to 4 carbon atoms, and d1 represents an integer of 0 or 1;
where A15 and A16 independently represent any of formulae (A101) to (A106), R105 and R106 independently represent a divalent hydrocarbon group having 1 to 4 carbon atoms, R107 represents a monovalent hydrocarbon group having 1 to 4 carbon atoms, and d2 represents an integer of 0 or 1;
A17-R108 O—R109 n1 A18 (4)
where A17 and A18 independently represent any of formulae (A101) to (A106), n1 represents an integer of 1 to 4, and R108 and R109 constitute a part of a linking group for making a distance corresponding to a straight chain formed of at least 4 carbon atoms and 1 oxygen atom between A17 and A18, and independently represent a divalent hydrocarbon group having 2 to 4 carbon atoms;
where A19 and A20 independently represent any of formulae (A101) to (A106), R112 represents a hydrogen atom, or a monovalent hydrocarbon group having 1 to 4 carbon atoms, and R110 and R111 constitute a part of linking group for binding A19 and A20, and independently represent a divalent hydrocarbon group having 2 to 4 carbon atoms, for making a distance corresponding to a straight chain of at least 2 carbon atoms between each of A19 and A20, and a nitrogen atom;
where A21 to A23 independently represent any of formulae (A101) to (A106), and R113 to R115 constitute a part of a linking group for binding A21 to A23, and independently represent a divalent hydrocarbon group having 2 to 4 carbon atoms, for making a distance corresponding to a straight chain of at least 2 carbon atoms between each of A21 to A23, and a nitrogen atom;
where R116 to R118 independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, and symbol “*” represents a bonding site with any of formulae (1) to (6);
where R119 and R120 independently represent a hydrocarbon group needed for forming a nitrogen-containing heteroaromatic six-membered ring in formula (A102), R121′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, d3 represents an integer of from 0 to 2, and symbol “*” represents a bonding site with any of formulae (1) to (6);
where R122 and R123 independently represent a hydrocarbon group needed for forming a nitrogen-containing heteroaromatic five-membered ring in formula (A103), R124 represents a hydrogen atom, or a monovalent hydrocarbon group having 1 to 12 carbon atoms, R125′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, d4 represents an integer of from 0 to 2, and symbol “*” represents a bonding site with any of formulae (1) to (6);
where R126 represents a hydrocarbon group needed for forming a nitrogen-containing heteroaromatic ring in formula (A104), R127′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, d5 represents an integer of from 0 to 2, and symbol “*” represents a bonding site with any of formulae (1) to (6);
where R128 represents a hydrocarbon group needed for forming a nitrogen-containing heterocyclic nonaromatic ring in formula (A105), R129 represents a hydrogen atom, or a monovalent hydrocarbon group having 1 to 12 carbon atoms, R130′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, d6 represents an integer of from 0 to 2, and symbol “*” represents a bonding site with any of formulae (1) to (6); and
where R131 and R132 independently represent a hydrocarbon group needed for forming a nitrogen-containing heterocyclic nonaromatic ring in formula (A106), R133 and R134 independently represent a hydrogen atom, or a monovalent hydrocarbon group having 1 to 12 carbon atoms, R135′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, d7 represents an integer of from 0 to 2, and symbol “*” represents a bonding site with any of formulae (1) to (6).
2. The electrophotographic member according to claim 1 , wherein the cation is represented by formula (1).
3. The electrophotographic member according to claim 2 , wherein R101 in formula (1) has a straight chain moiety of 6 or more carbon atoms.
4. An electrophotographic member, comprising:
an electroconductive substrate; and
an electroconductive resin layer on the substrate, wherein
the resin layer contains (i) an anion comprising at least one of a fluoroalkylsulfonylimide anion or a fluorosulfonylimide anion, and (ii) a resin having a structure selected from the group consisting of formulae (7) to (12) in a molecule
E11-R201-E12 (7)
where E11and E12 independently represent any of formulae (E101) to (E106), and R201 represents a linking group having a straight chain moiety of 4 or more carbon atoms, the linking group making a distance corresponding to a straight chain of 4 or more carbon atoms between E11 and E12;
where E13 and E14 independently represent any of formulae (E101) to (E106), R202 and R203 independently represent a divalent hydrocarbon group having 1 to 4 carbon atoms, R204represents a monovalent hydrocarbon group having 1 to 4 carbon atoms, and d8 represents an integer of 0 or 1;
where E15 and E16 independently represent any of formulae (E101) to (E106), R205 and R206 independently represent a divalent hydrocarbon group having 1 to 4 carbon atoms, R207 represents a monovalent hydrocarbon group having 1 to 4 carbon atoms, and d9 represents an integer of 0 or 1;
where E17 and E18 independently represent any of formulae (E101) to (E106), n2 represents an integer of 1 to 4 and R208 and R209 constitute a part of a linking group for making a distance corresponding to a straight chain formed of at least 4 carbon atoms and 1 oxygen atom between E17 and E18, and independently represent a divalent hydrocarbon group having 2 to 4 carbon atoms;
where E19 and E20 independently represent any of formulae (E101) to (E106), R212 represents a hydrogen atom, or a monovalent hydrocarbon group having 1 to 4 carbon atoms, and R210 and R211constitute a part of a linking group for binding E19 to E20, and independently represent a divalent hydrocarbon group having 2 to 4 carbon atoms, for making a distance corresponding to a straight chain of at least 2 carbon atoms between each of E19 and E20, and a nitrogen atom;
where E21 to E23 independently represent any of formulae (E101) to (E106), and R213 to R215 constitute a part of a linking group for binding E21 to E23, and independently represent a divalent hydrocarbon group having 2 to 4 carbon atoms, for making a distance corresponding to a straight chain of at least 2 carbon atoms between each of E21 to E23, and a nitrogen atom;
where X1 to X3 independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, at least one of X1 to X3 represents a bonding site with the resin, and symbol “*” represents a bonding site with any of formulae (7) to (12);
where R216 and R217 independently represent a hydrocarbon group needed for forming a nitrogen-containing heteroaromatic six-membered ring in formula (E102), X4′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, d10 represents an integer of 1 or 2, at least one of X4′s represents a bonding site with the resin, and symbol “*” represents a bonding site with any of formulae (7) to (12);
where R218 and R219 independently represent a hydrocarbon group needed for forming a nitrogen-containing heteroaromatic five-membered ring in formula (E103), X5 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, X6′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, d11 represents an integer of from 0 to 2, at least one of X5 and X6′s represents a bonding site with the resin, and symbol “*” represents a bonding site with any of formulae (7) to (12);
where R220 represents a hydrocarbon group needed for forming a nitrogen-containing heteroaromatic ring in formula (E104), X7′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, d12 represents an integer of 1 or 2, at least one of X7′s represents a bonding site with the resin, and symbol “*” represents a bonding site with any of formulae (7) to (12);
where R221 represents a hydrocarbon group needed for forming a nitrogen-containing heterocyclic nonaromatic ring in formula (E105), X8 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, X9′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, d13 represents an integer of from 0 to 2, at least one of X8 and X9′s represents a bonding site with the resin, and symbol “*” represents a bonding site with any of formulae (7) to (12); and
where R222 and R223 independently represent a hydrocarbon group needed for forming a nitrogen-containing heterocyclic nonaromatic ring in formula (E106), X10 and X11 independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 12carbon atoms, or a bonding site with the resin, X12′s independently represent a monovalent hydrocarbon group having 1 to 12 carbon atoms, or a bonding site with the resin, d14 represents an integer of from 0 to 2, at least one of X10 to X12′s represents a bonding site with the resin, and symbol “*” represents a bonding site with any of formulae (7) to (12).
5. The electrophotographic member according to claim 4 , wherein the bonding sites with the resin in X1 to X12′s are independently selected from the group consisting of formulae (X101) to (X105):
where symbol “* * ” represents a bonding site with a nitrogen atom in formulae (E101), or represents a bonding site with one of a nitrogen atom in a nitrogen-containing heterocycle and a carbon atom in the nitrogen-containing heterocycle in any of formulae (E102) to (E106), symbol “***” represents a bonding site with a carbon atom in a polymer chain forming the resin, and n3 to n7 independently represent an integer of 1 to 4.
6. The electrophotographic member according to claim 4 , wherein the resin has a structure represented by formula (7).
7. The electrophotographic member according to claim 6 , wherein R101 in formula (1) has a straight chain moiety of 6 or more carbon atoms.
8. The electrophotographic member according to claim 4 , wherein the nitrogen-containing heteroaromatic six-membered ring in formula (E102) is a pyrazine ring or a pyrimidine ring.
9. The electrophotographic member according to claim 4 , wherein the nitrogen-containing heteroaromatic five-membered ring in formula (E103) is an imidazole ring.
10. The electrophotographic member according to claim 4 , wherein the nitrogen-containing heteroaromatic ring in formula (E104) is a pyrrole ring, a pyridine ring, or an azepine ring.
11. The electrophotographic member according to claim 4 , wherein the nitrogen-containing heterocyclic nonaromatic ring in formula (E105) is a pyrrolidine ring, a pyrroline ring, a piperidine ring, an azepane ring, or an azocane ring.
12. The electrophotographic member according to claim 4 , wherein the nitrogen-containing heterocyclic nonaromatic ring in formula (E106) is an imidazolidine ring, an imidazoline ring, a piperazine ring, a diazepane ring, or a diazocane ring.
13. The electrophotographic member according to claim 4 , wherein the anion comprises a fluoroalkylsulfonylimide anion having a fluoroalkyl group having 1 to 6 carbon atoms, a four-to seven-membered cyclic perfluoroalkyldisulfonylimide anion, or a fluorosulfonylimide anion.
14. A process cartridge, which is configured to be detachably attachable to a main body of an electrophotographic apparatus, the process cartridge comprising the electrophotographic member of claim 4 .
15. An electrophotographic apparatus, comprising the electrophotographic member of claim 4 .