Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

1. An electrophotographic photosensitive member comprising:

a support; and a surface layer,

wherein the surface layer contains a cured product of a composition containing a curable hole-transport compound, a compound represented by the following formula (1), and a compound represented by the following formula (2),

in the formula (1), Rf 11 represents a divalent group having 3 or more carbon atoms and 6 or more fluorine atoms, R 12 and R 13 each independently represent a hydrogen atom, a fluorine atom, an acryloyloxy group, or a methacryloyloxy group, with the proviso that at least one of R 12 and R 13 is an acryloyloxy group or a methacryloyloxy group,

in the formula (2), R 21 and R 22 each independently represent an alkyl group having 1 or more and 4 or less carbon atoms, or a substituted or unsubstituted aryl group having 1 or more and 4 or less carbon atoms, the substituent, which can be a substituent of the aryl group, is an alkyl group having 1 or more and 4 or less carbon atoms, R 21 and R 22 may be joined together to form a ring, R 23 represents an alkyl group having 1 or more and 4 or less carbon atoms, R 24 and R 25 each independently represent a hydrogen atom or a methyl group, and R 26 and R 27 each independently represent an alkylene group having 1 or more and 4 or less carbon atoms.

2. The electrophotographic photosensitive member according to claim 1 , wherein, in the composition, when the mass of the curable hole-transport compound is denoted by A, the mass of the compound represented by the formula (1) is denoted by B, and the mass of the compound represented by the formula (2) is denoted by C, a ratio of A to the sum total of A, B, and C, which is A/(A+B+C), is 0.5 or more and 0.85 or less.

3. The electrophotographic photosensitive member according to claim 1 , wherein, in the composition, when the mass of the curable hole-transport compound is denoted by A, the mass of the compound represented by the formula (1) is denoted by B, and the mass of the compound represented by the formula (2) is denoted by C, a ratio of B to the sum total of A, B, and C, which is B/(A+B+C), is 0.1 or more and 0.2 or less.

4. The electrophotographic photosensitive member according to claim 1 , wherein, in the composition, when the mass of the curable hole-transport compound is denoted by A, the mass of the compound represented by the formula (1) is denoted by B, and the mass of the compound represented by the formula (2) is denoted by C, a ratio of C to the sum total of A, B, and C, which is C/(A+B+C), is 0.1 or more and 0.2 or less.

5. The electrophotographic photosensitive member according to claim 1 , wherein the surface layer is a protection layer, and the film thickness of the protection layer is 2 μm or more and 8 μm or less.

6. The electrophotographic photosensitive member according to claim 1 , wherein in an infrared spectrum obtained for the surface layer, when the maximum value of peak height within the wavenumber range of from 1100 cm −1 to 1125 cm −1 is denoted by D, and the maximum value of peak height within the wavenumber range of from 1700 cm −1 to 1770 cm −1 is denoted by E, the ratio of D to E, which is D/E, is 0.30 or more and 0.45 or less.

7. The electrophotographic photosensitive member according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (3), or a compound represented by the following formula (4),

(R 34 R 32 Rf 31 R 33 R 35 )  (3)

in the formula (3), Rf 31 represents a group in which 6 or more hydrogen atoms in the alkylene group are each substituted with a fluorine atom, R 32 and R 33 represent an alkylene group or a phenylene group, R 34 and R 35 are a hydrogen atom, a fluorine atom, a group represented by the following formula (5), or a group represented by the following formula (6), with the proviso that at least one of R 34 and R 35 is a group represented by the following formula (5) or a group represented by the following formula (6),

(R 44 Rf 42 R 41 Rf 43 R 45 )  (4)

in the formula (4), R 41 represents an alkylene group or a phenylene group, Rf 42 and Rf 43 each represent a group in which 3 or more hydrogen atoms in the alkylene group are each substituted with a fluorine atom, R 44 and R 45 represent a hydrogen atom, a fluorine atom, a group represented by the following formula (5), or a group represented by the following formula (6), with the proviso that at least one of R 44 and R 45 is a group represented by the following formula (5) or a group represented by the following formula (6),

in the formula (5), the symbol ** represents a position at which the group is bonded to each of R 32 , R 33 , R 42 , and R 43 , R 51 represents a single bond or an alkylene group having 1 or more and 6 or less carbon atoms, and R 52 represents a hydrogen atom or a methyl group,

in the formula (6), the symbol ** represents a position at which the group is bonded to each of R 32 , R 33 , R 42 , and R 43 , R 61 represents an alkylene group having 1 or more and 6 or less carbon atoms, R 62 represents a hydrogen atom or a methyl group, and subscript s represents an integer of 0 or more and 4 or less.

8. The electrophotographic photosensitive member according to claim 1 , wherein the curable hole-transport compound is a compound represented by the following formula (7):

in the formula (7), R 71 and R 72 each independently represent an alkyl group having 2 or more and 8 or less carbon atoms, R 73 and R 74 each independently represent a hydrogen atom or an alkyl group having 4 or less carbon atoms, R 75 and R 77 each independently represent an alkylene group having 3 or more and 6 or less carbon atoms, and R 76 and R 78 each independently represent a hydrogen atom or a methyl group.

9. The electrophotographic photosensitive member according to claim 1 , wherein at least one of R 21 and R 22 in the compound represented by the formula (2) is an alkyl group having 2 or more carbon atoms.

10. A process cartridge that is detachably attachable to an electrophotographic apparatus main body, and integrally supports:

an electrophotographic photosensitive member; and

at least one unit selected from the group consisting of a charging unit, a developing unit, a transfer unit, and a cleaning unit,

wherein the electrophotographic photosensitive member comprises a support and a surface layer,

the surface layer includes a cured product of a composition containing a curable hole-transport compound, a compound represented by the following formula (1), and a compound represented by the following formula (2),

in the formula (1), Rf 11 represents a divalent group having 3 or more carbon atoms and 6 or more fluorine atoms, R 12 and R 13 each independently represent a hydrogen atom a fluorine atom, an acryloyloxy group, or a methacryloyloxy group, with the proviso that at least one of R 12 and R 13 is an acryloyloxy group or a methacryloyloxy group,

in the formula (2), R 21 and R 22 each independently represent an alkyl group having 1 or more and 4 or less carbon atoms or a substituted or unsubstituted aryl group having 1 or more and 4 or less carbon atoms, a substituent, which can be a substituent of the aryl group, is an alkyl group having 1 or more and 4 or less carbon atoms, R 21 and R 22 may be joined together to form a ring, R 23 represents an alkyl group having 1 or more and 4 or less carbon atoms, R 24 and R 25 each independently represent a hydrogen atom or a methyl group, and R 26 and R 27 each independently represent an alkylene group having 1 or more and 4 or less carbon atoms.

11. An electrophotographic apparatus, comprising: an electrophotographic photosensitive member; and a charging unit, an exposing unit, a developing unit, and a transfer unit,

wherein the electrophotographic photosensitive member comprises a support and a surface layer,

the surface layer includes a cured product of a composition containing a curable hole-transport compound, a compound represented by the following formula (1), and a compound represented by the following formula (2),

in the formula (1), Rf 11 represents a divalent group having 3 or more carbon atoms and 6 or more fluorine atoms, R 12 and R 13 each independently represent a hydrogen atom, a fluorine atom, an acryloyloxy group, or a methacryloyloxy group, with the proviso that at least one of R 12 and R 13 is an acryloyloxy group or a methacryloyloxy group,

in the formula (2), R 21 and R 22 each independently represent an alkyl group having 1 or more and 4 or less carbon atoms, or a substituted or unsubstituted aryl group having 1 or more and 4 or less carbon atoms, a substituent, which can be a substituent of the aryl group, is an alkyl group having 1 or more and 4 or less carbon atoms, R 21 and R 22 may be joined together to form a ring, R 23 represents an alkyl group having 1 or more and 4 or less carbon atoms, R 24 and R 25 each independently represent a hydrogen atom or a methyl group, and R 26 and R 27 each independently represent an alkylene group having 1 or more and 4 or less carbon atoms.