JP2014029502A5 - - Google Patents

Claims (14)

An electrophotographic photosensitive member having a support, an electron transport layer formed on the support, and a photosensitive layer formed on the electron transport layer,
The electron transport layer is a cured film containing carbon atoms, nitrogen atoms and oxygen atoms,
The electrophotographic photoreceptor, wherein the electron transport layer satisfies the following formulas (1) to (3).
σ (C) ≦ 1.5 (1)
σ (N) ≦ 1.5 (2)
σ (O) ≦ 1.5 (3)
(In the formulas (1) to (3),
σ (C) is 10 points obtained when the ratio (atoms%) of the carbon atoms to all atoms excluding hydrogen atoms in the electron transport layer at 10 points was analyzed by X-ray photoelectron spectroscopy (ESCA). Indicates the standard deviation of the values.
σ (N) is 10 points obtained when the ratio (atoms%) of the nitrogen atoms to all atoms excluding hydrogen atoms in the electron transport layer at 10 points was analyzed by X-ray photoelectron spectroscopy (ESCA). Indicates the standard deviation of the values.
σ (O) is 10 points obtained when the ratio (atoms%) of the oxygen atoms to all atoms excluding hydrogen atoms in the electron transport layer at 10 points is analyzed by X-ray photoelectron spectroscopy (ESCA). Indicates the standard deviation of the values.
The ten points consist of the upper and lower points of the electron transport layer and eight points that divide the thickness of the electron transport layer into nine equal parts in the depth direction. ) The electrophotographic photosensitive member according to claim 1, wherein the standard deviations σ (C), σ (N), and σ (O) satisfy the following formulas (4) to (6).
σ (C) ≦ 1.0 (4)
σ (N) ≦ 1.0 (5)
σ (O) ≦ 1.0 (6)   The total of the carbon atom ratio, the nitrogen atom ratio, and the oxygen atom ratio in the electron transport layer is 90% or more and 100% or less (excluding hydrogen atoms having no measurement sensitivity in ESCA). 3. The electrophotographic photosensitive member according to 1 or 2.   The said electron carrying layer contains the hardened | cured material of the composition containing the electron carrying substance which has a polymeric functional group, the thermoplastic resin which has a polymeric functional group, and a crosslinking agent in any one of Claim 1 to 3. The electrophotographic photosensitive member described.   The electrophotographic photosensitive member according to claim 4, wherein the thermoplastic resin has a weight average molecular weight of 5,000 to 400,000.   The electrophotographic photosensitive member according to claim 5, wherein the thermoplastic resin has a weight average molecular weight of 5,000 to 300,000.   7. The polymerizable functional group of the electron transport material is at least one selected from the group consisting of a hydroxy group, a thiol group, an amino group, a methoxy group, and a carboxyl group. Electrophotographic photoreceptor.   The electrophotographic photosensitive member according to claim 4, wherein the electron transport material has a molecular weight of 1000 or less. The electrophotographic photosensitive member according to any one of claims 4 to 8, wherein the electron transport material is a compound represented by any one of the following formulas (A1) to (A9).

(In the formulas (A1) to (A9), R ¹⁰¹ ~ R ¹⁰⁶ , R ²⁰¹ ~ R ²¹⁰ , R ³⁰¹ ~ R ³⁰⁸ , R ⁴⁰¹ ~ R ⁴⁰⁸ , R ⁵⁰¹ ~ R ⁵¹⁰ , R ⁶⁰¹ ~ R ⁶⁰⁶ , R ⁷⁰¹ ~ R ⁷⁰⁸ , R ⁸⁰¹ ~ R ⁸¹⁰ , R ⁹⁰¹ ~ R ⁹⁰⁸ Are each independently a monovalent group represented by the following formula (A), hydrogen atom, cyano group, nitro group, halogen atom, alkoxycarbonyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group Or a substituted or unsubstituted heterocycle. One of the carbon atoms in the main chain of the alkyl group is O, S, NH, NR ¹⁰⁰¹ (R ¹⁰⁰¹ May be replaced by an alkyl group). The substituent of the substituted alkyl group is an alkyl group, an aryl group, an alkoxycarbonyl group, or a halogen atom. The substituent of the substituted aryl group or the substituted heterocyclic group is a halogen atom, a nitro group, a cyano group, an alkyl group, or a halogen-substituted alkyl group. Z ²⁰¹ , Z ³⁰¹ , Z ⁴⁰¹ And Z ⁵⁰¹ Each independently represents a carbon atom, a nitrogen atom, or an oxygen atom. Z ²⁰¹ R is an oxygen atom ²⁰⁹ And R ²¹⁰ Does not exist, Z ²⁰¹ R is a nitrogen atom ²¹⁰ Does not exist. Z ³⁰¹ R is an oxygen atom ³⁰⁷ And R ³⁰⁸ Does not exist, Z ³⁰¹ R is a nitrogen atom ³⁰⁸ Does not exist. Z ⁴⁰¹ R is an oxygen atom ⁴⁰⁷ And R ⁴⁰⁸ Does not exist, Z ⁴⁰¹ R is a nitrogen atom ⁴⁰⁸ Does not exist. Z ⁵⁰¹ R is an oxygen atom ⁵⁰⁹ And R ⁵¹⁰ Does not exist, Z ⁵⁰¹ R is a nitrogen atom ⁵¹⁰ Does not exist. )

(In Formula (A), at least one of α, β, and γ is a group having a substituent, and the substituent is selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group. At least one group selected, l and m are each independently 0 or 1, and the sum of l and m is 0 or more and 2 or less.
α is an alkylene group having 1-6 atoms in the main chain, an alkylene group having 1-6 atoms in the main chain substituted with an alkyl group having 1-6 carbon atoms, or a main chain substituted with a benzyl group. An alkylene group having 1 to 6 atoms, an alkylene group having 1 to 6 atoms in the main chain substituted with an alkoxycarbonyl group, or an alkylene group having 1 to 6 atoms in the main chain substituted with a phenyl group . These groups may have at least one group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent. One of the carbon atoms in the main chain of the alkylene group is O or S or NH or NR ¹⁹ (R ¹⁹ Is an alkyl group. ) May be replaced.
β represents a phenylene group, an alkyl-substituted phenylene group having 1 to 6 carbon atoms, a nitro-substituted phenylene group, a halogen-substituted phenylene group, or an alkoxy group-substituted phenylene group. These groups may have at least one group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent.
γ represents a hydrogen atom, an alkyl group having 1 to 6 atoms in the main chain, or an alkyl group having 1 to 6 atoms in the main chain substituted with an alkyl group having 1 to 6 carbon atoms. These groups may have at least one group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent. One of the carbon atoms in the main chain of the alkyl group is O or S or NH or NR ¹⁰⁰³ (R ¹⁰⁰³ Is an alkyl group. ) May be replaced. ) The electrophotographic photosensitive member according to any one of claims 4 to 9, wherein the thermoplastic resin having a polymerizable functional group has a structural unit represented by the following formula (D).

(In formula (D), R ⁶¹ Represents a hydrogen atom or an alkyl group. Y ¹ Represents a single bond, an alkylene group or a phenylene group. W ¹ Represents a hydroxy group, a thiol group, an amino group, a carboxyl group, or a methoxy group. ) The crosslinking agent is an isocyanate group, a blocked isocyanate group or a group ^{(R 1} is a hydrogen atom or an alkyl group) represented by _-CH 2 -OR ¹ claims 4 10 of a compound having 3 to 6, The electrophotographic photosensitive member according to any one of the above. The electrophotographic photosensitive member according to any one of claims 4 to 11 the molecular weight of the crosslinking agent is 1000 or less. An electrophotographic photosensitive member according to any one of claims 1 to 12 , and at least one means selected from the group consisting of a charging means, a developing means, a transfer means, and a cleaning means are integrally supported, and electrophotographic A process cartridge that is detachable from the device. The electrophotographic photosensitive member according to any one of claims 1 12, and a charging means, an exposure means, the electrophotographic apparatus having the developing means and the transfer means.