JP2014029485A5

JP2014029485A5 -

Info

Publication number: JP2014029485A5
Application number: JP2013118068A
Authority: JP
Filing date: 2013-06-04
Publication date: 2014-10-23
Anticipated expiration: 2033-06-04

Description

本発明は、支持体、該支持体上に形成された下引き層、該下引き層上に形成された感光層を有する電子写真感光体において、
該下引き層が下記式（１）で示される構造を有する硬化物を含有することを特徴とする電子写真感光体。 The present invention relates to an electrophotographic photoreceptor having a support, an undercoat layer formed on the support, and a photosensitive layer formed on the undercoat layer.
The electrophotographic photoreceptor, wherein the undercoat layer contains a cured product having a structure represented by the following formula (1).

式（１）中、Ｒ^１およびＲ^３は、それぞれ独立に、置換もしくは無置換の主鎖の原子数が１から１０のアルキレン基、または置換もしくは無置換のフェニレン基を示す。Ｒ^２は、単結合、置換もしくは無置換の主鎖の原子数が１から１０のアルキレン基、または置換もしくは無置換のフェニレン基を示す。該置換のアルキレン基の置換基は、アルキル基、アリール基、ヒドロキシ基、またはハロゲン原子である。該置換のフェニレン基の置換基は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシ基、アルキル基、またはハロゲン置換アルキル基である。Ｒ^９は、水素原子、またはアルキル基を示す。Ａ^１は、下記式（Ａ−１）〜（Ａ−６）で示されるいずれかの基を示す。Ｂ^１は、下記式（Ｂ−１）〜（Ｂ−３）のいずれかで示される基を示す。Ｄ^１は、下記式（Ｄ）で示される主鎖の原子数が５から１５の基である。Ｅ^１は、下記式（Ｅ−１）〜（Ｅ−８）のいずれかで示される基である。 In formula (1), R ¹ and R ³ each independently represents an alkylene group having 1 to 10 atoms in the substituted or unsubstituted main chain, or a substituted or unsubstituted phenylene group. R ² represents a single bond, a substituted or unsubstituted alkylene group having 1 to 10 atoms in the main chain, or a substituted or unsubstituted phenylene group. The substituent of the substituted alkylene group is an alkyl group, an aryl group, a hydroxy group, or a halogen atom. The substituent of the substituted phenylene group is a halogen atom, a nitro group, a cyano group, a hydroxy group, an alkyl group, or a halogen-substituted alkyl group. R ⁹ represents a hydrogen atom or an alkyl group. A ¹ represents any group represented by the following formulas (A-1) to (A-6). B ¹ represents a group represented by any of the following formulas (B-1) to (B-3). D ¹ is a group having 5 to 15 atoms in the main chain represented by the following formula (D). E ¹ is a group Ru indicated by any one of the following formulas (E-1) ~ (E -8).

式（Ｅ−１）〜（Ｅ−８）中、Ｘ ^１１〜Ｘ^１６、Ｘ^２１〜Ｘ^２９、Ｘ^３１〜Ｘ^３６、Ｘ^４１〜Ｘ^４８、Ｘ^５１〜Ｘ^５８、Ｘ^６１〜Ｘ^６６、Ｘ^７１〜Ｘ^７８、およびＸ^８１〜Ｘ^８８は、それぞれ独立に、単結合、水素原子、ハロゲン原子、アルコキシカルボニル基、カルボキシル基、シアノ基、ジアルキルアミノ基、ヒドロキシ基、複素環基、ニトロ基、置換もしくは無置換のアルコキシ基、または置換もしくは無置換のアルキル基を示す。
Ｘ ^１１〜Ｘ ^１６の少なくとも１つ、Ｘ ^２１〜Ｘ ^２９の少なくとも１つ、Ｘ ^３１〜Ｘ ^３６の少なくとも１つ、Ｘ ^４１〜Ｘ ^４８の少なくとも１つ、Ｘ ^５１〜Ｘ ^５８の少なくとも１つ、Ｘ ^６１〜Ｘ ^６６の少なくとも１つ、Ｘ ^７１〜Ｘ ^７８の少なくとも１つ、およびＸ ^８１〜Ｘ ^８８の少なくとも１つは、単結合である。
Ｚ^５１〜Ｚ^５２、Ｚ^６１〜Ｚ^６２、およびＺ^８１は、それぞれ独立に、酸素原子、Ｃ（ＣＮ）_２基、またはＮ−Ｒ^１１を示す。Ｒ^１１は、置換もしくは無置換のアリール基、または置換もしくは無置換のアルキル基を示す。 Wherein (E-1) ~ (E -8), X 11 ~X 16, X 21 ~X 29, X 31 ~X 36, X 41 ~X 48, X 51 ~X 58, X 61 ~X 66, X ^{71 to} X ⁷⁸ and X ^{81 to} X ⁸⁸ each independently represent a single bond , a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, a heterocyclic group, or a nitro group. Represents a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkyl group.
At least one of X ¹¹ to X ^{^16,} at least one of X 21 ^{to X ^29,} at least one of X 31 ^{to X ^36,} at least one of X 41 ^{to X ^48,} at least one of X 51 ^{to X 58,} at least one of X ⁶¹ to X ^{^66,} at least one of X 71 ^{to X 78,} at least one of and ^X 81 ^{to X 88} is a single bond.
Z ^{51 to} Z ⁵² , Z ^{61 to} Z ⁶² , and Z ⁸¹ each independently represent an oxygen atom, a C (CN) ₂ group, or N—R ¹¹ . R ¹¹ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group.

式（１）中、Ｒ^１およびＲ^３は、それぞれ独立に、置換もしくは無置換の炭素数１から１０のアルキレン基、または置換もしくは無置換のフェニレン基を示す。Ｒ^２は、単結合、置換もしくは無置換の炭素数１から１０のアルキレン基、または置換もしくは無置換のフェニレン基を示す。Ｒ^９は、水素原子、またはアルキル基を示す。Ａ^１は、下記式（Ａ−１）〜（Ａ−６）で示されるいずれかの基を示す。Ｂ^１は、下記式（Ｂ−１）〜（Ｂ−３）のいずれかで示される基を示す。Ｄ^１は、下記式（Ｄ）で示される主鎖の原子数が５から１５の基である。Ｅ^１は、下記式（Ｅ−１）〜（Ｅ−８）のいずれかで示される基である。 In formula (1), R ¹ and R ³ each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenylene group. R ² represents a single bond, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenylene group. R ⁹ represents a hydrogen atom or an alkyl group. A ¹ represents any group represented by the following formulas (A-1) to (A-6). B ¹ represents a group represented by any of the following formulas (B-1) to (B-3). D ¹ is a group having 5 to 15 atoms in the main chain represented by the following formula (D). E ¹ is a group Ru indicated by any one of the following formulas (E-1) ~ (E -8).

式（Ｅ−１）〜（Ｅ−８）中、Ｘ ^１１〜Ｘ^１６、Ｘ^２１〜Ｘ^２９、Ｘ^３１〜Ｘ^３６、Ｘ^４１〜Ｘ^４８、Ｘ^５１〜Ｘ^５８、Ｘ^６１〜Ｘ^６６、Ｘ^７１〜Ｘ^７８、およびＸ^８１〜Ｘ^８８は、それぞれ独立に、単結合、水素原子、ハロゲン原子、アルコキシカルボニル基、カルボキシル基、シアノ基、ジアルキルアミノ基、ヒドロキシ基、複素環基、ニトロ基、置換もしくは無置換のアルコキシ基、または置換もしくは無置換のアルキル基を示す。該置換アルコキシ基の置換基は、カルボキシル基、シアノ基、ジアルキルアミノ基、ヒドロキシ基、アルキル基、アルコキシ置換アルキル基、ハロゲン化アルキル基、アルコキシ基、アルコキシ置換アルコキシ基、ハロゲン置換アルコキシ基、ニトロ基、またはハロゲン原子である。該置換アルキル基の置換基は、カルボキシル基、シアノ基、ジアルキルアミノ基、ヒドロキシ基、アルキル基、アルコキシ置換アルキル基、ハロゲン化アルキル基、アルコキシ基、アルコキシ置換アルコキシ基、ハロゲン置換アルコキシ基、ニトロ基、またはハロゲン原子である。
Ｘ ^１１〜Ｘ ^１６の少なくとも１つ、Ｘ ^２１〜Ｘ ^２９の少なくとも１つ、Ｘ ^３１〜Ｘ ^３６の少なくとも１つ、Ｘ ^４１〜Ｘ ^４８の少なくとも１つ、Ｘ ^５１〜Ｘ ^５８の少なくとも１つ、Ｘ ^６１〜Ｘ ^６６の少なくとも１つ、Ｘ ^７１〜Ｘ ^７８の少なくとも１つ、およびＸ ^８１〜Ｘ ^８８の少なくとも１つは、単結合である。
Ｚ^５１〜Ｚ^５２、Ｚ^６１〜Ｚ^６２、およびＺ^８１は、それぞれ独立に、酸素原子、Ｃ（ＣＮ）_２基、またはＮ−Ｒ^１１を示す。Ｒ^１１は、置換もしくは無置換のアリール基、または置換もしくは無置換のアルキル基を示す。該置換のアリール基の置換基は、カルボキシル基、シアノ基、ジアルキルアミノ基、ヒドロキシ基、アルキル基、アルコキシ置換アルキル基、ハロゲン化アルキル基、アルコキシ基、アルコキシ置換アルコキシ基、ハロゲン置換アルコキシ基、ニトロ基、またはハロゲン原子である。該置換のアルキル基の置換基は、カルボキシル基、シアノ基、ジアルキルアミノ基、ヒドロキシ基、アルキル基、アルコキシ置換アルキル基、ハロゲン化アルキル基、アルコキシ基、アルコキシ置換アルコキシ基、ハロゲン置換アルコキシ基、ニトロ基、またはハロゲン原子である。 Wherein (E-1) ~ (E -8), X 11 ~X 16, X 21 ~X 29, X 31 ~X 36, X 41 ~X 48, X 51 ~X 58, X 61 ~X 66, X ^{71 to} X ⁷⁸ and X ^{81 to} X ⁸⁸ each independently represent a single bond , a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, a heterocyclic group, or a nitro group. Represents a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkyl group. The substituent of the substituted alkoxy group includes a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, an alkyl group, an alkoxy-substituted alkyl group, a halogenated alkyl group, an alkoxy group, an alkoxy-substituted alkoxy group, a halogen-substituted alkoxy group, and a nitro group. Or a halogen atom. The substituent of the substituted alkyl group includes a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, an alkyl group, an alkoxy-substituted alkyl group, a halogenated alkyl group, an alkoxy group, an alkoxy-substituted alkoxy group, a halogen-substituted alkoxy group, and a nitro group. Or a halogen atom.
At least one of X ¹¹ to X ^{^16,} at least one of X 21 ^{to X ^29,} at least one of X 31 ^{to X ^36,} at least one of X 41 ^{to X ^48,} at least one of X 51 ^{to X 58,} at least one of X ⁶¹ to X ^{^66,} at least one of X 71 ^{to X 78,} at least one of and ^X 81 ^{to X 88} is a single bond.
Z ^{51 to} Z ⁵² , Z ^{61 to} Z ⁶² , and Z ⁸¹ each independently represent an oxygen atom, a C (CN) ₂ group, or N—R ¹¹ . R ¹¹ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group. The substituent of the substituted aryl group includes a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, an alkyl group, an alkoxy-substituted alkyl group, a halogenated alkyl group, an alkoxy group, an alkoxy-substituted alkoxy group, a halogen-substituted alkoxy group, a nitro group A group, or a halogen atom. The substituent of the substituted alkyl group includes a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, an alkyl group, an alkoxy-substituted alkyl group, a halogenated alkyl group, an alkoxy group, an alkoxy-substituted alkoxy group, a halogen-substituted alkoxy group, a nitro group A group, or a halogen atom.

Claims

In an electrophotographic photosensitive member having a support, an undercoat layer formed on the support, and a photosensitive layer formed on the undercoat layer,
The electrophotographic photoreceptor, wherein the undercoat layer contains a cured product having a structure represented by the following formula (1).

(In formula (1), R ¹ and R ³ each independently represents an alkylene group having 1 to 10 atoms in the substituted or unsubstituted main chain, or a substituted or unsubstituted phenylene group. R ² represents Represents a single bond, an alkylene group having 1 to 10 atoms in the substituted or unsubstituted main chain, or a substituted or unsubstituted phenylene group, which can be an alkyl group, an aryl group, a hydroxy group, The substituent of the substituted phenylene group is a halogen atom, a nitro group, a cyano group, a hydroxy group, an alkyl group, or a halogen-substituted alkyl group, and R ⁹ is a hydrogen atom or an alkyl group A ¹ represents any group represented by the following formulas (A-1) to (A-6), and B ¹ represents any of the following formulas (B-1) to (B-3). Indicated by .D ¹ showing the group, .E ¹ is a group of 15 atoms in the main chain is from 5 represented by the following formula (D) is any one of the following formulas (E-1) ~ (E -8) in a indicated Ru group.)

(R ¹⁰ represents a hydrogen atom or an alkyl group.)

(In formulas (B-1) to (B-3), R ² represents a single bond, an alkylene group having 1 to 10 atoms of a substituted or unsubstituted main chain, or a substituted or unsubstituted phenylene group. R ⁶ and R ⁷ are each independently an alkylene group having 1 to 5 atoms in the main chain, or an alkylene group having 1 to 5 atoms in the main chain substituted with an alkyl group having 1 to 5 carbon atoms. An alkylene group having 1 to 5 atoms in the main chain substituted with a benzyl group, an alkylene group having 1 to 5 atoms in the main chain substituted with an alkoxycarbonyl group, or an atom in the main chain substituted with a phenyl group Represents an alkylene group having a number of 1 to 5. One of the carbon atoms in the main chain of the alkylene group may be replaced by O, S, NH or NR ^15. R ¹⁵ is an alkyl group Ar ² Is a substituted or unsubstituted phenylene group Shown. Substituents of phenylene group as said substituent include a halogen atom, a nitro group, hydroxy group, a cyano group, an alkyl group or .R ¹² is a halogenated alkyl group, it is .A ¹ and a hydrogen atom or an alkyl group A ² represents any group represented by the formulas (A-1) to (A-6), o, p and q are each independently 0 or 1, and o, p and q The sum is from 1 to 3. * represents the side bonded to R ³ in the above formula (1).

(In formula (D), R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently substituted with an alkylene group having 1 to 5 atoms in the main chain and an alkyl group having 1 to 5 carbon atoms. An alkylene group having 1 to 5 atoms in the main chain, an alkylene group having 1 to 5 atoms in the main chain substituted with a benzyl group, and an alkylene group having 1 to 5 atoms in the main chain substituted with an alkoxycarbonyl group Or an alkylene group having 1 to 5 atoms in the main chain substituted with a phenyl group, and one of the carbon atoms in the main chain of the alkylene group may be replaced by O, S, NH or NR ¹⁵ R ¹⁵ is an alkyl group, Ar ¹ and Ar ² each independently represents a substituted or unsubstituted phenylene group, and the substituted phenylene group includes a halogen atom, a nitro group, a hydroxy group, Cyano group, alkyl A ² represents a group represented by any one of the formulas (A-1) to (A-6), and l, m, n, o, p and q are Each independently 0 or 1, and the sum of l, m and n, and the sum of o, p and q is 1 or more and 3 or less.)

(In the formula (E-1) ~ (E -8), X 11 ~X 16, X 21 ~X 29, X 31 ~X 36, X 41 ~X 48, X 51 ~X 58, X 61 ~X 66 , X ^{71 to} X ⁷⁸ , and X ^{81 to} X ⁸⁸ are each independently a single bond , a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a carboxyl group, a cyano group, a dialkylamino group, a hydroxy group, a heterocyclic group, nitro A group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkyl group;
At least one of X ¹¹ to X ^{^16,} at least one of X 21 ^{to X ^29,} at least one of X 31 ^{to X ^36,} at least one of X 41 ^{to X ^48,} at least one of X 51 ^{to X 58,} at least one of X ⁶¹ to X ^{^66,} at least one of X 71 ^{to X 78,} at least one of and ^X 81 ^{to X 88} is a single bond.
Z ^{51 to} Z ⁵² , Z ^{61 to} Z ⁶² , and Z ⁸¹ each independently represent an oxygen atom, a C (CN) ₂ group, or N—R ¹¹ . R ¹¹ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group. )

The electrophotographic photosensitive member according to claim 1 , wherein the cured product further has a structure represented by the following formula (2).

(In Formula (2), R ⁸ represents a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. The substituent of the substituted alkyl group having 1 to 5 carbon atoms is an alkyl group or an aryl group. Or a halogen atom.)

Wherein in D ^1, electrophotographic photosensitive member according to claim 1 or 2 atoms of the main chain represented by the formula (D) is 10 to 15 groups.

R ⁴ , R ⁵ , R ⁶ and R ⁷ in the formula (D) are each independently an alkylene group having 1 to 5 atoms in the main chain of methyl group or ethyl group substitution, or the number of atoms in the main chain The electrophotographic photoreceptor according to any one of claims 1 to 3 , wherein is an alkylene group of 1 to 5.

Formula (D) is Ar ¹ and Ar ² in the electrophotographic photosensitive member according to claim 1, any one of 4 is a phenylene group.

An electrophotographic photosensitive member according to any one of claims 1 to 5 , 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 main unit.

The electrophotographic photosensitive member according to any one of claims 1 5, as well as, a charging means, an exposure means, the electrophotographic apparatus having the developing means and the transfer means.