Electrophotographic member, process cartridge, and electrophotographic apparatus

1. An electrophotographic member, comprising:

an electroconductive substrate; and

an electroconductive resin layer on the electroconductive substrate,

wherein the electroconductive resin layer contains:

a resin having, in a molecule, at least one cation structure selected from the group consisting of the following formulae (1) to (13) and (29); and

an anion, and

wherein the anion comprises at least one selected from the group consisting of a fluorinated sulfonylimide anion, a fluorinated alkylsulfonylimide anion, a fluorinated sulfonyl methide anion, a fluorinated alkylsulfonyl methide anion, a fluorinated sulfonate anion, a fluorinated alkylsulfonate anion, a fluorinated carboxylate anion, a fluorinated borate anion, a fluorinated phosphate anion, a fluorinated arsenate anion, a fluorinated antimonate anion, a dicyanamide anion, and a bis(oxalato)borate anion:

in the formulae (1) to (4):

R1 to R8 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (1) to (4) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R9 and R10 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

one of two N's represents N + ;

in the formulae (5) to (9):

R11 to R15 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (5) to (9) to form a five-membered ring, a six-membered ring, or a seven-membered ring; and

R16 represents a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms;

in the formulae (10) to (13) and (29):

R17 to R20 and R47 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (10) to (13) and (29) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R21, R22, and R48 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

in the formulae (10) to (13), one of two N's represents N + ;

in the formulae (1) to (13) and (29):

X1 to X34 each independently represent a structure represented by the following formula (A), (b), or (c):

in the formula (A), (b), or (c):

symbol “*” represents a bonding site with a nitrogen atom in the nitrogen-containing heterocycle or a carbon atom in the nitrogen-containing heterocycle in the formulae (1) to (13) and (29);

symbol “**” represents a bonding site with a carbon atom in a polymer chain of the resin; and

n1, n2, and n3 each independently represent an integer of 1 or more and 4 or less.

2. An electrophotographic member according to claim 1 , wherein the resin has, in the molecule, at least one cation structure selected from the formulae (3), (4), (8), (9), (12), (13), and (29).

3. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (1) or the formula (2) comprises a structure represented by the following formula (1-1) or the following formula (2-1), respectively

4. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (3) comprises a structure represented by the following formula (3-1)

5. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (5) comprises a structure represented by the following formula (5-1)

6. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (6) or the formula (7) comprises a structure represented by the following formula (6-1) or the following formula (7-1), respectively

7. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (8) comprises a structure represented by the following formula (8-1)

8. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (10) or the formula (11) comprises a structure represented by the following formula (10-1) or the following formula (11-1), respectively

9. An electrophotographic member according to claim 1 , wherein the structure represented by the formula (29) comprises a structure represented by the following formula (29-1)

10. An electrophotographic member, comprising:

an electroconductive substrate; and

an electroconductive resin layer on the electroconductive substrate,

wherein the electroconductive resin layer contains a resin comprising a reaction product between an ionic compound having at least one cation selected from the group consisting of the following formulae (14) to (26) and (28), and a compound capable of reacting with a glycidyl group:

in the formulae (14) to (17):

R23 to R30 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (14) to (17) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R31 and R32 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

one of two N's represents N + ;

in the formulae (18) to (22):

R33 to R37 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (18) to (22) to form a five-membered ring, a six-membered ring, or a seven-membered ring; and

R38 represents a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms;

in the formulae (23) to (26) and (28):

R39 to R42 and R45 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (23) to (26) and (28) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R43, R44, and R46 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

in the formulae (23) to (26), one of two N's represents N + ; and

in the formulae (14) to (26) and (28):

Y1 to Y34 each independently represent a structure represented by the following formula (27):

in the formula (27),

n represents an integer of 1 or more and 4 or less.

11. An electrophotographic member according to claim 10 , wherein the ionic compound comprises at least one anion selected from the group consisting of a fluorinated sulfonylimide anion, a fluorinated alkylsulfonylimide anion, a fluorinated sulfonyl methide anion, a fluorinated alkylsulfonyl methide anion, a fluorinated sulfonate anion, a fluorinated alkylsulfonate anion, a fluorinated carboxylate anion, a fluorinated borate anion, a fluorinated phosphate anion, a fluorinated arsenate anion, a fluorinated antimonate anion, a dicyanamide anion, and a bis(oxalato)borate anion.

12. A process cartridge, which is removably mounted onto a main body of an electrophotographic apparatus, the process cartridge comprising at least one electrophotographic member comprising:

an electroconductive substrate; and

an electroconductive resin layer on the electroconductive substrate,

wherein the electroconductive resin layer contains:

a resin having, in a molecule, at least one cation structure selected from the group consisting of the following formulae (1) to (13) and (29); and

an anion, and

wherein the anion comprises at least one selected from the group consisting of a fluorinated sulfonylimide anion, a fluorinated alkylsulfonylimide anion, a fluorinated sulfonyl methide anion, a fluorinated alkylsulfonyl methide anion, a fluorinated sulfonate anion, a fluorinated alkylsulfonate anion, a fluorinated carboxylate anion, a fluorinated borate anion, a fluorinated phosphate anion, a fluorinated arsenate anion, a fluorinated antimonate anion, a dicyanamide anion, and a bis(oxalato)borate anion:

in the formulae (1) to (4):

R1 to R8 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (1) to (4) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R9 and R10 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

one of two N's represents N + ;

in the formulae (5) to (9):

R11 to R15 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (5) to (9) to form a five-membered ring, a six-membered ring, or a seven-membered ring; and

R16 represents a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms;

in the formulae (10) to (13) and (29):

R17 to R20 and R47 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (10) to (13) and (29) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R21, R22, and R48 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

in the formulae (10) to (13), one of two N's represents N + ;

in the formulae (1) to (13) and (29):

X1 to X34 each independently represent a structure represented by the following formula (A), (b), or (c):

in the formula (A), (b), or (c):

symbol “*” represents a bonding site with a nitrogen atom in the nitrogen-containing heterocycle or a carbon atom in the nitrogen-containing heterocycle in the formulae (1) to (13) and (29);

symbol “**” represents a bonding site with a carbon atom in a polymer chain of the resin; and

n1, n2, and n3 each independently represent an integer of 1 or more and 4 or less.

13. An electrophotographic apparatus, comprising:

an electrophotographic photosensitive member; and

at least one electrophotographic member comprising:

an electroconductive substrate; and

an electroconductive resin layer on the electroconductive substrate,

wherein the electroconductive resin layer contains:

a resin having, in a molecule, at least one cation structure selected from the group consisting of the following formulae (1) to (13) and (29); and

an anion, and

wherein the anion comprises at least one selected from the group consisting of a fluorinated sulfonylimide anion, a fluorinated alkylsulfonylimide anion, a fluorinated sulfonyl methide anion, a fluorinated alkylsulfonyl methide anion, a fluorinated sulfonate anion, a fluorinated alkylsulfonate anion, a fluorinated carboxylate anion, a fluorinated borate anion, a fluorinated phosphate anion, a fluorinated arsenate anion, a fluorinated antimonate anion, a dicyanamide anion, and a bis(oxalato)borate anion:

in the formulae (1) to (4):

R1 to R8 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (1) to (4) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R9 and R10 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

one of two N's represents N + ;

in the formulae (5) to (9):

R11 to R15 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (5) to (9) to form a five-membered ring, a six-membered ring, or a seven-membered ring; and

R16 represents a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms;

in the formulae (10) to (13) and (29):

R17 to R20 and R47 each independently represent a hydrocarbon group needed for a nitrogen-containing heterocycle in each of the formulae (10) to (13) and (29) to form a five-membered ring, a six-membered ring, or a seven-membered ring;

R21, R22, and R48 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less carbon atoms; and

in the formulae (10) to (13), one of two N's represents N + ;

in the formulae (1) to (13) and (29):

X1 to X34 each independently represent a structure represented by the following formula (A), (b), or (c):

in the formula (A), (b), or (c):

symbol “*” represents a bonding site with a nitrogen atom in the nitrogen-containing heterocycle or a carbon atom in the nitrogen-containing heterocycle in the formulae (1) to (13) and (29);

symbol “**” represents a bonding site with a carbon atom in a polymer chain of the resin; and

n1, n2, and n3 each independently represent an integer of 1 or more and 4 or less.