WO1993007540A1

WO1993007540A1 - Electrophotographic photoreceptor

Info

Publication number: WO1993007540A1
Application number: PCT/JP1992/001241
Authority: WO
Inventors: Akihiko Kurahashi
Original assignee: Idemitsu Petrochemical Co., Ltd.
Priority date: 1991-09-30
Filing date: 1992-09-29
Publication date: 1993-04-15
Also published as: JPH0588382A; EP0564655A4; EP0564655A1

Abstract

An electrophotographic photoreceptor having a photoconductive layer formed on a conductive substrate and coated with a protective layer prepared from a composition comprising a reactive (di)pentaerythritol compound, a reactive phosphazene compound and a reactive siloxane compound. The photoreceptor is excellent in abrasion resistance, surface smoothness, heat resistance, moisture resistance and so forth.

Description

Specification

Electrophotographic photoreceptor

• li i'f; i-field

The present invention relates to an electrophotographic photoreceptor, in particular, by coating the surface with a protective layer made of a specific composition, or by including the above composition in a photo-exclusive layer constituting the outermost layer. Electrophotographic photoreceptors with greatly improved wear resistance, wear resistance, heat resistance, heat resistance, moisture resistance, etc.

9 '' o

Technology background

Generally, in an electronic device using the Carlson method incorporating an electrophotographic photosensitive member, such as a copying machine, a laser beam printer, or a light emitting diode printer, first, the surface of the electrophotographic photosensitive member is corona-discharged. Charge, then exposing the required portion, selectively removing the static charge in the exposed portion to form an electrostatic latent image, and then attaching a developer called toner to the static latent image Thereafter, the developer is transferred and fixed to paper, whereby an electrophotograph is formed.

Conventionally, this type of electrophotographic photoreceptor has a single photoconductive layer formed on the surface of a conductive support, but the electrophotographic photoreceptor has (1) a potential of (2) that the surface potential leaks away in some places (potential holding ability), (3) the surface potential rapidly decreases during light irradiation (photo-responsiveness), etc. Characteristics are required. Therefore, in recent years, in order to meet these demands, there has been a multi-layered light-separating layer in which the functions of charge generation and load transfer (transport) are performed in separate layers. Electrophotographic photoreceptors with conductive layers have also appeared O

Whether the photoconductive layer is a single layer or multiple layers, The printing speed of the apparatus has been further increased, and the apparatus itself has been reduced in size, and the process time per print (the time of charging, exposing, and developing / removing) tends to be shortened. For this reason, a large mechanical load is applied to the photoconductive layer. This mechanical load is caused by the contact of the electrophotographic photoconductor with the blade brush in the cleaning device, which cleans the toner, toner, paper, and the toner slightly attached to the surface of the electrophotographic photoconductor. Caused by The higher the repetition of the series of steps of charging-exposure-development-elimination ε, the greater the mechanical load applied to the electrophotographic photosensitive layer. Therefore, there is a problem that the surface of the electrophotographic light-sensitive device 4 becomes significantly worn and its usable life is shortened.

Further, it is expected that a higher printing speed in the future will increase the number of printed sheets per side of the electrophotographic photosensitive member. In this case, the wear resistance is reduced in terms of the mechanical life of the electrophotographic photosensitive member. Need to be improved o

Therefore, in order to improve the wear resistance of the surface of the electrophotographic photosensitive member, it has been proposed to form a wear-resistant protective layer on the outermost layer of the electrophotographic photosensitive member. For example, as a resin for forming a protective layer, a silicone resin (see Japanese Patent Application Laid-Open No. Sho 62-75460) and an epoxy resin (see Japanese Patent Application Laid-Open No. Sho 53-107341) ), Melamine resin (see Japanese Patent Application Laid-Open No. 61-217502), fluororesin (see Japanese Patent Application Laid-Open No. 60-115,644), acryl resin (ex. (Refer to the public announcement of No. 54-35 338).

However, in these known techniques, the intended purpose of abrasion resistance may not be sufficient, the electrophotographic properties may be rather deteriorated, or the density may be reduced or capri may occur. Also, There is a problem in that the performance of the photoreceptor is remarkably changed due to environmental changes, particularly environmental humidity, and it is easy to cause image defects such as print disturbance and capri, which are called image deletion.

Further, as a proposal other than the above, according to Japanese Patent Application Laid-Open No. 57-87964, polycarbonate and a curable resin are often exemplified as a binder resin for forming a protective layer. Are not fully satisfactory in terms of adhesion, strength, surface hardness, etc.

On the other hand, JP-A-63-35856 and JP-A-63-56658 disclose protection obtained by adding a fluorine-containing resin powder to polycarbonate, polyester, or the like. Electrophotographic photoreceptors formed from layers have been proposed. However, according to these proposals, although the slip property of the electrophotographic photoreceptor can be improved, there is a problem that the film strength and the surface hardness are rather lowered.

Disclosure of departure

Under these circumstances, the present inventors have conducted intensive research in order to overcome the above-mentioned problems of the conventional technology. As a result, the protective layer of the electrophotographic photoreceptor contains an en-reactive phenol erythritol compound or a reactive dipentyl erythritol compound, (2) a reactive phosphazene compound, and (3) a reactive siloxane compound. It has been found that the object can be achieved by forming the outermost layer to contain the above composition instead of forming with the composition described above or forming the protective layer.

The present invention has been completed based on such findings.

That is, according to the present invention, the photoconductive layer formed on the conductive substrate comprises: (1) 90 to 40 mol% of a reactive penyl erythritol compound or a reactive dipentyl erythritol compound; 100 parts by weight of a mixture comprising 100 to 60 mol% of a reactive phosphazene compound and (3) O also provides an electrophotographic photoreceptor characterized by being coated with protective dust consisting of a composition containing 0.1 to 50 parts by weight of the ft-siloxane compound. The present invention also provides an electrophotographic photoreceptor comprising the above composition in a photoconductive layer (especially the outermost layer thereof) instead of forming the above-mentioned protective layer.

BEST MODE FOR CARRYING OUT THE INVENTION

In the present invention, when a protective layer is formed on the surface of the photoconductive layer in the electrophotographic photoreceptor, the protective layer itself is formed using the above composition, or the surface of another protective layer is formed using the above composition. Cover with object. When such a protective layer is not formed, the above-described composition is contained in the photoconductive layer (particularly, the outermost layer portion).

As described above, the composition used in the present invention comprises (1) a reactive benzoyl erythritol compound or a reactive dipentyl erythritol compound, (2) a reactive phosphazene compound, and (3) a reactive siloxane compound. It contains. In this composition, the above-mentioned (1) reactive (di) pentaerythritol compound, (2) reactive phosphazene compound and (3) reactive siloxane compound react with each other, or And cured by reacting with the compound of the formula (1). In other words, the above composition in the present invention includes (1) a group derived from a reactive (di) pentaerythritol compound, (2) a group derived from a reactive phosphazene compound, and (3) a group derived from a reactive siloxane compound. It means a composition containing a group derived therefrom, particularly a cured product thereof.

Here, (1) the reactive pen erythritol compound is represented by the general formula

CH ₂ R ²

I

RC l 2 one ^ H 2 R [Wherein, R ′ to R ⁴ are each —H, —OH, —R (R is an alkyl group having 1 to 10 carbon atoms), —OR (R is the same as above), or C CH = CH ₂ or — OCC (CH ₃ ) = Indicates an organic containing CH 2. However, at least of R] ~R ⁴ one "^ 3

-OC CH = CH ₂ or — OCC (CH ₃ ) = CH ₂ containing organic :! It is. ] It is a compound represented by these. Of these, those in which two or more, and especially three or more, of R ^{1 to} R ⁴ are —〇 CCH = CH ₂ or — OCC (CH ₃ ) = organic groups containing CH ₂ are reactive. High and preferred.

The reactive dipentyl erythritol compound is represented by the general formula

C H 2 C Γ1 2

I I

R ⁵ CH ₂ — C— CH ₂ —〇 CH ₂ — C— CH ₂ R ⁸

IICH ₂ R ¹⁰ CH ₂ R ⁹

[Wherein, R ^{5 to} R ^{1 ()} are each 1 H, —OH, —R (R is an alkyl group having 1 to 10 carbon atoms), —OR (R is as defined above), or —H C CH = CH ₂ or an organic group containing OCC (CH ₃ ) = CH 2. However, at least one of R ^{5 to} R is

— 0 C CH = CH ₂ or —〇 CC (CH ₃ ) = Organic containing CH ₂ . ]

It is a compound represented by these. Of these, in particular, R ^{5 to} R ^{1 (} two or more, particularly three or more, of 1 — 0 C CH 2 CH ₂ or

-0 CC (CH ₃ ) = an organic group containing CH ₂ is preferred because of its high reactivity.

Here, as typical organic groups containing 100 C CH = CH ₂ or 100 CC (CH ₃ ) = CH ₂ , -00 C CH = CH ₂ ,-00 CC (CH ₃ ) = CH ₂ ,

-0-CH ₂ CH (CH ₃ ) 0 CCH = CH, ₂ ,

-0-CH ₂ CH (CH ₃ ) 0 ½-0 CC (CH ₃ ) = CH ₂ ,

― 0-^ 0C-CH ₂ CH ₂ CH2CH ₂ CH ₂ 0- ^ 0CCH = CH2

Etc. 7j, glue.

These reactive penyl erythritol compounds or reactive dipentyl erythritol compounds may be used alone or in a mixture. Further, as long as the composition does not affect the hardness of the composition, it may contain a (di) benzoyl erythritol compound partially free of a reactive group. In general, 90 to 0 or more is reactive (di) pen-hu erythritol.

Next, (2) a reactive phosphazene compound represented by the general formula (I)

[NP (A) a (B) _b ] _n ■, · (I)

Wherein A represents a curable group, B represents a non-curable group,

a and b are real numbers that satisfy a> 0, h ≥ 0, and a + b = 2. N represents an integer of 3 or more. ]

Compounds having the structure represented by are preferred. Here, the general formula (I) does not indicate a single compound, but indicates an average value of a mixture of several compounds. Therefore, a and b indicating the number of each group are not necessarily limited to integers, but are real numbers including decimal numbers. Similarly, n is a real number including not only an integer in the range of 3 or more, usually 3 to 18, and preferably 3 to 4, but also a decimal number. There are various phosphazene compounds having a repeating unit represented by the above general formula (I) depending on the type of each substituent.

In the formula, A represents a curable group, which is an ultraviolet ray, a visible ray, It means a functional group that cures by irradiation with light or electron beam, use of a chemical curing agent, or heating, etc. It is usually a group having a reactive double bond. As the group having the reactive double bond, there are various kinds of force, for example, an acryloyl group (10 CCH = CH ₂ ), a methyl acryloyl group (100 CC ( CH ₃ )-CH ₂ ) or

And functional groups containing a hydroxyl group (—CH ₂ CH = CH ₂ ).

The functional group containing an acryloyl group or the 7-functional group containing a methacryloyl group is an acryloyloxy group ゃ a methacryloyloxy group, or a compound represented by the general formula (II)

R ¹³

CH ₂ = i— C— 0— R 0_ · · · (II)

II

〇

[In the formula, R ¹³ represents a hydrogen atom or a methyl group, and R ¹⁴ represents an alkylene group having 1 to 12 (preferably 1 to 5) carbon atoms (including a branched alkylene group). ]

It is the one that is given by

Specific examples of the group represented by the general formula (II) include 2-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, and 3-hydroxypropyl methacrylate. , 2—Hydroxybutyl methacrylate, 3—Hydroxybutyl methacrylate, 4—Hydroxybutyl methacrylate, 5—Hydroxypentyl methacrylate, 6—Hydroxy-3 — Methylhexylmethacrylate, 5—Hydroxyhexylmethacrylate, 3—Hydroxy-1 2—t—Butylpropyrmethacrylate, 3—Hydroxy-1,2,2-Dimethylhexylmeth Tactylate, 3-hydroxy-2-methyl-1-ethyl Residues obtained by removing hydrogen atoms from hydroxyl groups in methacrylates such as propyl methacrylate and 12-hydroxy dodecyl methacrylate, and 2-hydroxyhexyl acrylate, '2— Hydroxip mouth pyracylate, 3-hydroxypropyrylate, 2-hydroxypyrylacrylate, 3-hydroxybutylacylate, 4-hydroxybutylatarylate , 5-hydroxypentyl acrylate, 6-hydr π-xy-13-methylhexyl acrylate, 5-hydroxy hexyl acrylate, 3-hydroxy 2-t-butyl propyl acrylate Relate, 3-hydroxy-2,2-dimethylhexyl acrylate, 3-hydroxy-12-methyl-1-ethyl C-pyracrelate and 1 2 arsenide Dorokishi Dodeshiruaku relay Bok § click Li rate hydroxyl residue obtained by removing a hydrogen atom from being such as the can and elevation Geruko. Particularly preferred groups are a 2-hydroxyquinethyl methacrylate residue and a 2-hydroxyxethyl acrylate residue. The functional groups contained include, in addition to those of the above general formula (II), general formula (III) R ¹³ H

CH ₂ = i— C— N— R ^{, 4} 0— · ■ · (III)

II

〇

Wherein R ¹³ and R ¹⁴ are the same as above. ]

A residue obtained by removing a hydrogen atom from a hydroxyl group of a hydroxyalkyl-substituted acrylamide-hydroxyl-substituted methacrylamide, In addition, the general formula (IV)

R 1 3

C H ■ C— NH (IV)

II

〇

[Wherein, R ′ ³ is the same as described above. ]

And the residue obtained by removing one hydrogen atom from the amino group of acrylamide (methacrylamide).

Et al is, the functional group containing Ariru group, § Lil group ho of itself, is not limited Ariruokishi group _{_{(CH 2 = CH- CH 2 0-}} ) but are this O § Riruokishi group, wide, generally Formula (V)-(VI

R ¹³ R ' ⁵

CH ₂ = i— i— 0 one-·-(V)

R ¹⁶

R ¹³

I 0—

C H: C—C H 〇 '(VI) or

R ¹³

C H: (VII)

[Formula width, R ¹³ is the same as above. R ¹⁵ and R ¹⁶ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]

And a residue obtained by removing a hydrogen atom from the hydroxyl group of the aryl group having one hydroxyl group. This general formula

Specific examples of the functional groups represented by (V) to (VII) include: CH ₂ = .CH-CH ₂ -OH, CH ₂ = CH- CH-OH

CH ₃

CH ₂ = CH— C-OH, CH ₂ C-CH ₂ —〇H

I I

CH ₃ CH ₃ ,

C H: CH— CH

C H: C H— C H 〇 H

CH = C-C Η ₂ · 〇 OH

CH ₃

There is a residue obtained by removing the hydrogen atom from the hydroxyl group in aryl compounds such as

—B in the general formula (I) is not particularly limited, for example, the general formula

R】 ⁷ M— · · · (VIII)

No ^^

lo Represents a group represented by Here, in the formula (VIII), M represents an oxygen atom, sulfur J¾i-Τ · or an imino group, and R ¹⁷ represents an alkyl group having 1 to 18 carbon atoms or a 1 to 18 carbon atom. Shows a halogenated alkyl group. Specifically, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and halogens (eg, fluorine, chlorine, bromine, etc.) Alkylthio groups such as alkoxy group, methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, heptylthio group, octylthio group, halogen (eg, fluorine, salt:, bromine, etc.) )), The same alkylthio group, methylimino ”, ethylimino group, propylimino group, butylimino group, pentylimino group, hexylimino group, heptylimino group, octylimino group Alkyl imino groups such as mino groups, halogens (for example, fluorine, chlorine, ) Ru can and Ageruko similar Arukirui Mi Roh group substituted by. Further, the formula (IX) medium M is as defined above, R ^{1 8} ~R ^{2 2} Waso respectively independently a hydrogen atom, a halogen atom, 1 to 4 carbon atoms the alkyl group or the number of 1 to 4 carbon Shows a halogenated alkyl group. The group of the formula (IX) is a phenoxy group, a thiophenyl group, a halogenated phenoxy group (2, 4, 6-tribromophenoxy group, a 4-bromobromooxy group, a 2—clo Phenoxy groups, 2,4-dichlorophenoxy groups, etc. and halogenated thiophenyl groups (eg, 4-chlorophenylthio groups), some compounds, phthalocyanine and halogenated anilines (2-chloro) Residues obtained by removing the hydrogen atom from the amino group of aniline, 2,4-dichloroaniline, 2,4,6-tribromoaniline, etc. can be mentioned.

For a and b in the general formula (I), a + b = 2 It should be a real number that satisfies, and is usually a compound having two or more curable groups, preferably 0 <a ≤ 2, 0 ≤ b <2.

The substituent A is a group that acts when the film containing the phosphazene compound of the general formula (I) is cured, and the substituent B regulates the physical properties of the cured product and the curing performance. It is a group showing an action. Therefore, by appropriately selecting a and b, various physical properties of the cured film containing the phosphazene compound are defined. However, a compound containing no curability A does not have curability, and thus such a phosphazene compound is excluded from the components of the composition of the present invention. However, a = 2, b = 0, that is, the general formula (（)

-6NP (A) d

The phosphazene compound having a repeating unit represented by the following formula can be used as a component of the composition of the present invention.

The reactive phosphazene compound in the present invention is a compound having a recurring unit of the above general formula (I). The force n is in the range of 3 to 18, especially 3 to 4 or a mixture thereof. Optimal. The repeating unit of the general formula (I) may be linked in a chain form, but is preferably linked cyclically.

Furthermore, there are various (3) reactive siloxane compounds used in the present invention.

〇 Z

Wherein R ¹¹ and R ¹² each represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to ¹² carbon atoms, and Z ¹ and Z ² represent These represent hydrogen or organic residues, respectively. Further, m is however a positive integer, one even ^Z] and Z ² of the rather small for, - 0 CCH = CH ₂ the other is a group containing a -〇 _{_{CC (CH 3) = CH 2}} . ]

Compounds represented by the following formulas are preferred.

Furthermore, the following general formula

Or

The compound represented by is also preferable.

In the above formula, a block copolymer is shown for convenience, but other random copolymers may be used. Here, in the equation, k and p are integers from 0 to 400, q is an integer from 10 to 100, and r is an integer from 2 to 100. Y is a group derived from a diisocyanate compound, for example, a group derived from 2,4-tolylene diisocyanate or a group derived from methylene diphenyl diisocyanate. X is a group containing (meta) acrylate, for example, 2-hydroxyhexyl (meta) acrylate, pentaerythritol monohydride, pheasant (meta) acrylate There are groups derived from erythritol monohydroxypentyl (meta) acrylate. Further, R ²³ is a straight-chain or branched alkyl group or a single bond (S and Si are ^ -bonded), and R ²⁴ and R ²⁵ each have 1 carbon atom. To 4 alkyl groups or phenyl groups. As this reactive siloxane compound, a compound synthesized separately may be used, or may be formed in a reaction system.

These reactive siloxane compounds may be used alone or as a mixture. Further, as long as the composition does not affect the hardness of the composition, the composition may contain a siloxane compound having no reactive group. In general, the reactive siloxane compound is above 90%.

The composition used in the present invention comprises (1) a reactive pentaerythritol compound or a reactive dipentyl erythritol compound, (2) an anti-I-phosphazene compound and (3) a reactive siloxane compound as main components. The mixing ratio of these (1) to (3) is (1) based on the total of (1) the reactive (di) pentaerythritol compound and (2) the reactive phosphazene compound. Properties (di) Pencil erythritol compound 90 to 40 mol%, preferably 80 to 50 mol%, (2) reactive phosphazene compound 10 to 60 mol%, preferably 20 to 50 mol% Further, based on a total of 100 parts by weight of the (1) reactive (di) phenol erythritol compound and (2) the reactive phosphazene compound,

(3) The proportion of the reactive siloxane compound should be adjusted to 0.1 to 50 parts by weight, preferably 0.5 to 30 parts by weight.

(1) Reactivity (di) The pen-erythritol compound is effective in increasing the hardness of the formed protective debris ^ and contributes to the improvement of wear resistance. However, if the compounding ratio is too large, the curing rate is too high, and cracks are likely to occur. Furthermore, separation 1 when used as an electrophotographic photoreceptor may be reduced.

In order to prevent this cracking, (2) a reactive phosphazene compound is effective, and the slip property is improved to solve the problem of separation. (3) The reactive siloxane compound works effectively.

Therefore, by using a composition in which each of the above components (1) to (3) is blended in the above ratio, the electrophotographic photoreceptor can be provided with abrasion resistance, slipperiness, release property, heat resistance, moisture resistance, and the like. Can be provided in a well-balanced manner.

As the conductive substrate constituting the electrophotographic photoreceptor of the present invention, various substrates can be used as long as they have conductivity and can ground the photoconductive layer. Specific examples of the conductive substrate include aluminum, aluminum alloy, copper, zinc, stainless steel, vanadium, molybdenum, chromium, titanium, nickel, indium, gold, and platinum. Other conductive substrates include, for example,

(プラス Plastics (eg, polyethylene, aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide alloy, tin oxide alloy) having a coating layer of various metals or compounds (for example, aluminum, aluminum alloy, indium oxide, indium oxide alloy, tin oxide alloy) formed by a vacuum evaporation method. Polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, polyethylene fluoride, etc.)

(2) Conductive particles (aluminum powder, titanium oxide, tin oxide, zinc oxide, carbon black, etc.) together with a suitable binder are made of a plastic substrate or the same material as the conductive substrate. Such as a structure that is coated on a base

(3) Plastic paper impregnated with conductive particles

Alternatively, (4) a plastic having a conductive polymer can be used.

An undercoat (adhesive layer) having a barrier function and an undercoat function may be present on the surface of the substrate. This undercoat layer improves the adhesion of the photoconductive layer, improves coating properties, protects the substrate, covers defects on the substrate, Various forms such as improvement of charge injection property from the body and protection against electrical breakdown of the photoconductive layer can be formed according to the purpose.

Materials for forming the undercoat layer include polyvinyl alcohol and poly-vinyl alcohol.

Examples include N-vinylimidazo, polyethylene oxide, ethylcellulose, methylcellulose, ethylene-acrylic acid copolymer, casein, polyamide, copolymerized nylon, nylon, and gelatin. The undercoat layer can be formed by a known method.

In the electrophotographic photoreceptor of the present invention, a photoconductive layer is formed on the conductive substrate as described above. Here, the photoconductive layer is formed in a single layer or a multilayer.

First, when the photoconductive layer is formed as a single layer, its components include, for example, Se, Se—Te alloy, Se—As alloy, Se—Sb alloy, and Se—B. An organic photoreceptor such as an i-alloy vapor-deposited film such as a polypinylcarbazole / trinitole / fluorenone or amorphous silicon can be used.

When forming an organic light-sensitive layer (photoconductive layer) such as polyvinyl carbazole trinitrofluorenone, the composition (that is, (1) reactive (di) pentaerythritol compound, (2) reactive The cured product of the phosphazene compound and (3) a composition containing a reactive siloxane compound) is preferably used as the binder.

When a photoconductive layer is formed from a cured product of this composition, the content of the organic photoconductor in the photoconductive layer is arbitrarily determined according to the desired photosensitivity. When a photoconductive layer is formed using the composition, a monofunctional monomer or a polyfunctional monomer may be added to the composition as necessary.

Further, this composition is used by mixing with a solvent if necessary. On this occasion Examples of the solvent used in the process include ketones such as methylethyl ketone, methyl isobutyl ketone, and cyclohexanone; aromatic hydrocarbons such as benzene, toluene, and xylene; Halogenated hydrocarbons such as form and methylene chloride, alcohols such as methanol, ethanol, propanol and butanol, and ethers such as tetrahydrofuran and dioxane. Organic solvents such as ethyl ethyl solvent and ethyl cellosolve, and the like. These solvents may be used alone or in combination of two or more.

Among them, ketones, alcohols or a mixed solvent thereof are preferred, and particularly, methylisobutylketone is preferably a mixed solvent with isopropyl alcohol or butyl alcohol.

In addition, the composition serves as a cured body for protecting the photoconductive layer. Here, the curing means includes an active energy ray (visible light ray, ultraviolet ray, electron beam, X-ray, Irradiation (light curing), heat curing, and room temperature curing can be used as appropriate. When an organic photoreceptor is used as the photoconductive layer, it is preferable that the photocurable layer be cured with active energy in order to prevent deterioration of organic substances.

When photo-curing is used, for example, when a curing method using ultraviolet light or visible light is used, ^ 1-hydroxycyclohexyl phenyl ketone, dibenzoyl, benzoinolemethyl ether, benzol as a polymerization initiator It is possible to add ylethyl ether, p-chlorobenzophenone, p-methoxybenzophenone, benviyl peroxide, di-tert-butyl benzoxide and camphuaquinone. I like it. These photopolymerization initiators may be used alone or in combination of two or more.

The amount of the curing accelerator used is usually 100 parts by weight of the composition. It is selected in the range of 0.05 to 10.0 parts by weight.

In addition, when using thermal curing, when using the aging curing method or the room temperature curing method, a peroxide compound or an amine O compound may be used alone or in combination as a polymerization initiator. preferable. Examples of peroxide-based compounds include benzoyl peroxide; P- □□ benzoyl peroxide: 2,4-dichlorobenzoic oxide; t-butyl hydroperoxide; t-butyl hydroperoxide; —Oxide; Dicumyl peroxyside; t—Butyl veroxy acetate; Diacetate; t Monobutyl peroxybenzoate. Examples of amide-based compounds include N,! \ ^Τ- diethanol-P-toluidine; dimethyl-toluidine; ρ-toluidine; methylamine; t-butylamine: methylethylchomin; diphenylamine; 4,4'-dinitrodiphenylamine;0-nitroaniline;p-promoline; 2,4,6-tribromoaniline.

In this case, the total im amount of the peroxide-based compound and the amine-based compound is selected in a range of 0.05 to 5.0 parts by weight Pff based on 100 parts by weight of the composition. Is preferred.

In order to form a photoconductive layer by curing the composition of the present invention, the composition, and if necessary, a monofunctional monomer or a polyfunctional monomer, the photoreceptor, a solvent, and a curing initiator are used. A photoconductive layer composition is prepared, and the composition is cured directly on the surface of the conductive substrate or through an undercoat layer.

Means and methods of ¾ cloth, conventionally known method, for example, spinner U _r spray method, Roruko Isseki of the Act, di-up method, when applied by ^ city methods such as brushing, using a solvent Then removes the solvent Leave. ,

Next, room temperature curing, heat curing, or irradiation with ultraviolet rays, electron beams, X-rays, X-rays, etc., cures the curable composition to form a cured coating film.

The thickness of the photoconductive layer formed using the composition of the present invention is usually

0.01 to 100 0m.

The single-layer photoconductive layer can be formed by using another binder resin without forming the cured product of the composition. In this case, the photoconductive layer is formed on the photoconductive layer. Furthermore, as described later, it is preferable to provide a protective layer made of a cured product of the composition of the present invention.

Next, when the photoconductive layer is formed in multiple layers, it becomes a function-separated type photoconductive layer. The function-separated type photoconductive layer formed in the multilayer includes a charge generation layer and a charge transfer layer (charge transfer layer). In this case, the charge generation layer and the charge transfer layer are sequentially laminated on the conductive substrate (that is, the conductive substrateΖthe charge generation layer and the charge transfer layer), but are laminated in the reverse order ( That is, the conductive substrate (charge transfer layer / charge generation layer) may be used. Here, the charge generation layer contains a charge generation material of an organic or inorganic pigment and a binder tree Hi !. Examples of the charge-generating substance include azoxybenzene, disazo, trisazo, benzimidazole, polycyclic quinoline, indigoide, quinacridone, phthalocyanine, and periphery. Pigments and dyes that are known to generate charges, such as len-based, perinon-based, cyanine dyes, (thio) pyrilyum salts, and square-riium dyes, can be mentioned. These pigments are described in, for example,

4 7 — 3 7 5 4 3, 4 7 — 3 7 5 4 4, 4 7 — 1 8 5 5 4 3, 4 7 — 1 8 5 4 4, 4 8 — 4 3 No. 942, No. 48 — 7 0 5 3 8 No., No. 49-1 No. 1 2 3 1, No. 4 9-10 5 5 No. 3, 6 No. 5 These are exemplified in the publications of Nos. 0 to 75214 and 50 to 92738. Of these pigments, phthalocyanine pigments are preferred. Further, among the lipocyclic cyanine-based pigments, those described in JP-A-58-182640 and JP-A-92-255 are disclosed. ', 7? And? The 7'-type metal-free phthalocyanine is particularly preferable because it has high sensitivity up to a long wavelength. In addition to the above pigments, it is also possible to use any organic pigment that generates a load carrier by light irradiation.

Examples of the binder resin include a polycarbonate resin, a polyester resin, an acrylic resin, a polyvinyl formal, a polyvinyl butyral, an epoxy resin, and a urethane resin.

^ The blending ratio of the binder resin in the load generating layer is 5 to 400 parts by weight, more preferably 10 to 300 parts by weight, based on 100 parts by weight of the charge generating agent. If the amount is less than 5 parts by weight, the density of the charge generation layer with the conductive substrate is poor, and the film of the charge generation layer may be uneven or the image may be deteriorated. If it exceeds, the sensitivity tends to decrease and the residual potential tends to increase.

If necessary, additives such as a plasticizer, an antifoaming agent, a fluidity improving agent, a pinhole controlling agent, a coupling agent, and an antioxidant may be added to the charge generating layer.

For the charge generation layer, a dispersion is prepared by dispersing the charge generation agent, the binder resin, and an additive that is added as necessary in a solvent, and dip coating or roll coating is performed. It can be formed by coating on a conductive substrate by a method such as one-time application of apriquet, one-time application of wire, or the like.

Examples of the solvent include acetate, methylethylketone, and tetrahydrogen. Mouth furan; Toluene; Kyzylene; Dichloromethane; 1,2-Dichloroethane; 1,1,2—Trichloroethane; Methasol; Isopropyl alcohol.

The thickness of the charge generation layer is from 0.001 to 10 1m, preferably from 0.01 to 5 // m. If it is less than 0.01 / m, it may not be possible to form the charge generation layer uniformly, while if it exceeds 10 m, the above-mentioned performance such as chargeability may be reduced. .

The charge transfer layer (charge transfer layer) is formed to include a charge transfer substance (charge transfer substance) and a binder resin. Examples of the charge transfer material include fluorene; fluorenone; 2,7-dinitro-9-fluorenone; 3,7-dinitrodibenzothiophene-5-oxide; 1-bromopyrene; 2-vinyl; carnoxol; 3—phenylcarnoxole; 2—phenylindole; 2—phenylnaphthalene; oxazole; oxaziazol; oxatriazole; Rifenylamin; imidazole; chrysene; tetraphene; acridene; various hydrazones; styryl compounds; 1, 1-bis (p-pethylethylaminophenyl) 1-4, 4-Diphenyl 1, 3-Bubuten; 1 Ferro-3 — (4-Jetilaminostyryl)-5-(4-Jetilaminophenyl) Pilabri 2-phenyl-4-(4-dimethylaminophenyl) 1-5-phenyloxazole; poly-N-vinylcarbazole; halogenated poly-N-vinyl chloride; polyvinyl pyrene; polyvinyl pyrene; Polyvinyl benzothiophene; polyvinyl anthracene; polyvinyl acridine; polyvinyl villazolin. These can be used alone or in combination of two or more. (3) The composition of the present invention is suitable as a binder resin in the transport layer, and this is the same as in the case of forming a single photoconductive layer.

However, the compounding ratio of the composition of the present invention and the charge transfer material is preferably selected so that the ratio of the charge transfer material is usually 20 to 80 parts by weight based on the sum of these. The thickness of the charge transfer layer formed of the cured product of the composition is usually 5 to 50 m, preferably 8 to 30 fim. If it is less than 50 μm, the chargeability may decrease, and if it exceeds 50 m, the sensitivity and the light responsiveness tend to decrease.

The method for forming the charge transfer layer using the composition of the present invention is the same as that for forming a single photoconductive layer. The thickness of the charge transfer layer formed using this composition is usually 5 to 50 m, preferably 8 to 30 m. If it is less than 5 m, the chargeability may be reduced, and if it is more than 50 m, sensitivity and photoresponsiveness may be reduced.

Incidentally, in order to form a charge transfer layer without using the composition of the present invention as a binder resin, it is preferable to employ a binder resin as described below. When the charge transfer layer is formed using the binder resin described below, it is preferable to provide a protective layer (described later) formed using the composition of the present invention on the surface of the charge transfer layer.

Binder resins other than the composition of the present invention include, for example, polycarbonate resins, polyester carbonate resins, styrene resins, acrylic resins, silicone resins, polyester resins, phenoxy resins, and polyrelate. Resin, polysulfone resin, polyetherimide resin, vinyl acetate / vinyl chloride copolymer resin, poly (N-vinylcarbazole) resin, and the like. One of these can be used alone, or two or more of them can be used in combination. The compounding amount of the binder resin is usually 20 to 80% by weight based on the total amount of the charge transfer material and the binder resin. If the amount is less than 20% by weight, the photoresponsiveness may decrease. If the amount exceeds 80% by weight, the durability may be poor.

If necessary, additives such as a plasticizer, an antifoaming agent, a fluidity improver, a pinhole controlling agent, a coupling agent, and an antioxidant may be added to the charge transfer layer.

For the charge transfer layer, a dispersion is prepared by dispersing the charge transfer agent, the binder resin, and an additive to be added as necessary in a solvent, and dip coating or roll coating the dispersion. It can be formed by coating on the charge generating layer by a method such as coating, coating of apricot, coating of a wire, coating of a wire, or the like.

As the solvent, the same solvent as used for forming the charge generation layer can be used.

The thickness of the charge transfer layer is usually 5 to 50 / m, and preferably 8 to 30 m. If it is less than 5 Aim, the chargeability may decrease, and if it exceeds 50 m, sensitivity and photoresponsiveness may decrease.

In the present invention, the protective layer is not essential, but when formed, is formed on the surface of the photoconductive layer. However, when the protective layer is not formed, the composition of the present invention is always contained in the photoconductive layer (particularly, the outermost layer).

In the wood invention, the protective layer may be formed of a cured product of the composition, or may be a coating layer formed of another material, and a cured layer of the composition formed on the surface thereof. It may be formed by. If the case where the protective layer is formed of a cured body of the composition is described, It is as follows. In this case, the types and mixing ratios of the constituent components of the composition, or the types of monofunctional or polyfunctional monomers, solvents, and curing initiators that are optionally added to the composition are as described above. It is. In order to further improve the lubrication, a lubricant such as silicone wax may be added. Alternatively, the charge transfer material and the additives exemplified in the description of the charge transfer layer may be appropriately compounded.

When a protective layer is formed from the cured product of the composition of the present invention, a powder of a metal or a metal oxide may be dispersed during the protection. Metals dispersed in the protective layer include, for example, aluminum and aluminum alloys, and metal oxides dispersed in the protective layer include tin dioxide, antimony dioxide, zinc oxide, titanium oxide, tin oxide, and oxides. Indium, bismuth oxide, and the like can be given.

These metal or metal oxide powders preferably have an average particle size of 0.3 m or less. The content of these metals or metal oxides is usually at most 80% by weight, preferably at most 60% by weight. Addition of a powder of these metals or metal oxides provides a static elimination effect and improves electrophotographic properties.

The protective layer formed of the cured product of the composition of the present invention may contain, for example, a fluorine-containing resin powder as a lubricant. Specific examples of the fluorine-containing resin powder include tetrafluoroethylene, ethylene trifluoride, ethylene hexafluoride, propylene hexafluoride, vinyl fluoride, vinylidene fluoride, ethylene dichloride diethylene chloride, and trifluoropropyl methyl dichloride. Examples include polymers such as lucirane, copolymers thereof, and powders of copolymer resins with vinyl chloride. When the protective layer itself is formed from a cured product of the composition of the present invention, the thickness of the protective layer is Adjust to an arbitrary thickness in the range of 0.01 to 100 mm, preferably 0.5 to 15 mm, or more preferably 1.5 to 10 mm as necessary I can do it. When the thickness is less than 0.01 m, the function as a protective layer is not sufficiently exhibited, and the abrasion resistance may be reduced.On the other hand, when the thickness exceeds 100 m, sensitivity and light responsiveness are reduced. However, the residual potential may increase. Further, the protective layer formed by the cured product of the composition may be a laminate composed of a plurality of layers.

As another embodiment of the protective layer in the present invention, there is an iV. Protective layer comprising a coating layer formed of another material and a cured layer of the composition of the present invention formed on the surface thereof. The explanation is as follows. Other materials from which the coating film can be formed include: polyurethane tree) jl, polycarbonate resin, polyacrylate resin, polymethacrylate resin, polyisocyanate. A reaction product of an isocyanate and a polyester or polyether containing a hydroxyl group, or a reaction product of a polyisocyanate and an acrylic or epoxy resin containing a hydroxy group, or a polyisocyanate and a temporarily masked isocyanate group Reaction products with the polyisocyanate-containing prepolymer can be mentioned.

This coating layer can be formed by a coating method, a dipping method, a spraying method, a post-drying method, a curing method, or the like. The thickness of the coating layer is usually 0.5 to 10 m. The coating layer may contain the above-mentioned metal or metal sulphate.

The cured layer formed on the surface of the coating layer is the same as the case where the protective layer itself is formed from the cured product of the composition of the present invention. However, in this case, the thickness of the cured layer of the composition is 0.2 to 10 μm, and preferably, 0.5 to 5 μm. Although the shape of the electrophotographic photoreceptor of the present invention described in detail above is not particularly limited, it is usually formed in a drum shape.

Next, the present invention will be described in more detail with reference to Synthesis Examples, Examples and Comparative Examples.

Synthesis Example 1 (Production of reactive phosphazene compound)

Hexachlorocyclotriphosphazene was placed in a 1-liter flask equipped with a thermometer, stirrer, dropping funnel and condenser.

(Formula (NPC 1 ₂₎ ₃ of cyclic compounds) 5 8. 0 g (0. 1 6 7 mol), preparative儿E down 5 0 ml and pyridinium gin 1 6 8 g (2. 0 moles) And started the agitation.

Next, 14.3 g (1.1 mol) of 2-hydroxyethyl methacrylate was gradually dropped from the dropping funnel. The mixture was heated to 60 ° C. in a water bath, and the reaction was carried out for 8 hours with stirring. Then, the precipitated crystals were separated by filtration, the solvent in the obtained filtrate was removed by distillation under reduced pressure, and the residue was sufficiently dried to obtain 13.8 g of a yellow liquid. The yield was 91%. As a result of analysis, the product was found to be viscous 1,1,3,3,5,5-hexa- (hexylacryloylethylenedioxy) cyclotriphosphazene

It was (formula _{_{[NP (OC 2 H 4 0 2}} CC (CH 3) = CH 2) 2 ] a cyclic phosphazene compound represented by _3).

Synthesis Example 2 (Production of reactive siloxane compound) ...

In a 50 O cc flask equipped with a thermometer and a stirrer, 50 g (18 mmol) of polydimethylsiloxane (terminal alcohol) with a hydroxyl value of 1400 and 2,4—trirange isocyanate (TDI) (10 g, 57 mmol) was added, and the mixture was reacted at 60 for 8 hours. As a result of the analysis, a reaction mixture containing polydimethylsiloxane having no hydroxyl group and TDI bound at the end was obtained. Synthesis Example 3 (Production of reactive siloxane compound)

A 500 cc flask equipped with a thermometer and a stirrer was charged with 50 g (18 mimol) of polydimethylsiloxane (hydroxyl alcohol) having a hydroxyl value of 100 and hexamethylene diisocyanate ( HMDI) (7 g, 42 millimoles) was added and reacted at 60 ° C for 8 hours. As a result of the analysis, a reaction mixture containing polydimethylsiloxane having no hydroxyl group and having HMDI bound at the end was obtained.

Comparative Example 1 (Production of electrophotographic photoreceptor)

6.0 parts by weight of a polyimide resin (manufactured by Nippon Rilsan Co., Ltd., trade name: M995 (solid content: 100% by weight)) was completely dissolved in 94 parts by weight of a 1: 1 mixed solvent of methanol and dichloromethane. The obtained solution was dip-coated on an aluminum plate having a thickness of 0.1 mm, and dried at 120 at 40 minutes to form an intermediate layer having a thickness of 0.2 m.

Next, 2.5 parts by weight of metal-free phthalocyanine, 5.0 parts by weight of silicone resin (trade name: KR-255 (solid content: 50% by weight), manufactured by Etsu Chemical Co., Ltd.) and methyl ethyl ketone The mixed solution containing 92.5 parts by weight was put into a ball mill (pot mill manufactured by Nippon Chemical Ceramics Co., Ltd.) and kneaded and dispersed for 24 hours to obtain a dispersion for forming a charge generation layer. This dispersion was applied onto the above-mentioned intermediate layer by a dip coating method, and dried at 120 ° C. for 60 minutes to form a charge generation layer having a thickness of 0.3 m.

In addition, p-Jetylaminobenzaldehyde-diphenylhydrazone 6.0 parts by weight, polycarbonate resin (viscosity average molecular weight:

(27, 000, solid content: 100% by weight) 1.0 part by weight, 50 parts by weight of dichloromethane, and 1,1,2—30 parts by weight of trichloromethane are mixed and dissolved. Thus, a solution for a charge transfer layer was obtained. This solution was used for the charge generation layer. The surface was applied by dip coating and dried at 110 ° C. for 60 minutes to form a charge transfer layer having a thickness of 16 μm, thereby obtaining a photoreceptor (No. R 1).

The characteristics of this photoreceptor (No. R 1) were measured by the following methods. Table 1 shows the conclusions.

Comparative Example 2 (Production of electrophotographic photoreceptor)

To 10 g of multifunctional polyacrylate (Nippon Kayaku Co., Ltd., Colorado DPHA), 5 g of photoinitiator (Merck Co., Ltd., Darocure 1173) 1, conductive powder (toughened titanium) 5 g, 20 g of methylethylketone and 30 g of isobutanol were added to obtain a coating agent.

^ Charge coating of the photoreceptor (No. R1) was applied to the surface of the photoreceptor (No. R 1). ^ The solvent was removed, and then UV irradiation (30 seconds) was performed. Was formed.

The photoreceptor having this protective layer was measured in the same manner as in Comparative Example 1. Table 1 shows the results.

(1) Evaluation of electrophotographic characteristics

The following measurements were performed using an electrostatic recording paper tester (Kawaguchi Electric Co., Ltd., SP-428) using a photoreceptor sample of 60 x 70 mm square. Initial potential (V.), the sample 1, 0 0 0 a is rotated by rotation of the speed 'et al, potential attenuation of when irradiated with corona one 5 kV 1 0 seconds (Vk = V ₃₀ ZV., V ₃₀ represents the potential after ₃₀ seconds), and the half-life exposure amount (E ₅₀ ) represents the amount of light required for irradiating 10 lux of white light and then bringing the potential to 1 Z2. Residual potential (V _R) represents a potential after irradiation with white light 6 0 seconds.

(2) Endurance test

Using the same photoreceptor sample that was used for the evaluation of the microphotograph characteristics, the edge band (surface potential: -1,100 ± 100 V) and static elimination (static elimination light wave After repeating the length of 500 nm and the exposure amount of 50 mJZm ² ) 100,000 times, the electrophotographic characteristics were measured and compared with the initial values.

(3) Surface hardness

Using a Haydon surface property measuring device manufactured by Shinzuka Kagaku Co., Ltd., the steel wool (# 0000) was reciprocated 100 times with a 500 gZcm ² -ί weight, and then evaluated visually. did.

() Wear test

Using the abrasion test manufactured by Rikka Kasei Kogyo Co., Ltd., the surface of the same photoreceptor sample that was used for the evaluation of the electrophotographic characteristics was tested with a urethane rubber blade (load: 200 g) with a rubber hardness of 70. The sample was slid 200 times per minute, and the weight of the photoreceptor sample worn for 20 minutes was measured.

(5) Release test

The contact angle of water was measured using a contact angle meter CA-D manufactured by Kyowa Interface Science Co., Ltd.

(6) Adhesion

In accordance with JISK 540, a separation test was carried out using cellophane tape with a grid.

Example 1

The reactive phosphazene compound (1,1,3,3,5,5—hexa (methacryloylethylenedioxy) cyclotriphosphazene) obtained in Synthesis Example 1 above was added to 1 liter flask. g (255 mm), Penyu Erythritol Tonolate Crylate 250 g (839 mimol), and 10 g of the reaction mixture obtained in Synthesis Example 2 above. , And the mixture was heated to 60 ° C in a warm bath and reacted for 24 hours with stirring to obtain an I · pulverized body. No isolated group was observed in this dense body. Next, 10 g of this viscous body was added to a photoinitiator (Daroc, Merck). 1 1 7 3) 1 g, conductive powder (titanium oxide) 5 g, methyl ethyl ketone 20 g, and isobutanol 30 g were added to make a coating agent. The obtained coating solution is applied to the surface of the charge transfer layer of the photoreceptor (No. R 1), and after removing the solvent, irradiation (30 seconds) forms a protective layer having a thickness of 4 / zm. did. The photoreceptor having this protective layer is referred to as No. 1.

The characteristics of this photoconductor No. 1 were measured in the same manner as in Comparative Example 1. Table 1 shows the results.

Example 2

In a 1 liter flask, the reactive phosphazene compound (1,1,3,3,5,5—hexa (methacryloylethylenoxy) cyclotriphosphazene) obtained in Synthesis Example 1 was added. 2 g (255 mmol), dipentaerythritol hexaacrylate 150 g (260 mmol), dipentyl erythritol monohydroxypentaacrylate 100 g (189 mmol) ) And 50 g of the reaction mixture obtained in Synthesis Example 3 were added, and the mixture was heated to 60 in a warm bath and reacted for 24 hours with stirring to obtain a viscous body. No NCO groups were found in this viscous body.

To 1 g of this dense body, a photoinitiator (Irgacure 907, manufactured by Ciba Geigy Co., Ltd.) 1, 3 g of conductive powder (tin oxide), 20 g of methylethylketone, and 30 g of isobutanol were added. And a coating agent.

Using this coating agent, Photoconductor No. 2 having a protective film was obtained in the same manner as in Example 1 above.

The characteristics of this photoconductor No. 2 were measured in the same manner as in Comparative Example 1. Table 1 shows the results. Table 1 Evaluation> Item Comparative Example 1 Comparative Example 2

<

Electrophotography V. (-V) 1 1 1 0 1 0 6 0 Characteristics V _k (%) 8 9 8 8

E _5. (Look <>

(Initial) s · seconds) 1. 6 1. 7

V _R (-V) 0 0 Electrophotograph 1 1 0 0 1 0 6 0 Characteristics V _k (%) 9 0 8 9

(Durability) E _5. (Le-Nox · second) 1.5 1.1.8

0 0 Surface hardness Scratch No scratch Abrasion (mg) 2.5 0.5 Releasability 6 8 7 0 Adhesion 70/100 Visual test of paint film Some cracks

Table 1 (Overall)

Evaluation item Example 1 Example 2

Electrophotography Vo (-V) 1 0 6 0 1 1 2 0 Characteristics V _k (%) 8 8 8 9

>>

(Initial) E so (le '/ cs · sec) 1. 4 1. 7

V _R (-V) 0 0 Electrophotograph 1 0 8 0 1 1 1 0 Characteristics 8 4 8 8

(Durability) E _5. (Task · second) 1. 7 1. 9

0 0 Surface hardness No scratch No scratch Abrasion (mg) 0.6 6 0.4 Elevation 9 2 9 4 Adhesion 100/100 100/100 Visual inspection of coating film No abnormality No abnormality

Industrial availability

As described above, in the electrophotographic photoreceptor of the present invention, when a protective layer is formed, there is no separation or damage of the protective film, the thin protective layer has sufficient strength, but only the distortion of the protective layer, etc. And has excellent electrophotographic properties.

In addition, when the photoconductive layer is formed by adding the composition of the present invention, the photoconductive layer is not damaged, the thin photoconductive layer has sufficient strength, and the photoconductive layer can be distorted. There is no such thing.

Therefore, the electrophotographic photoreceptor of the present invention has significantly improved abrasion resistance, surface slippage, heat resistance 11 :, moisture resistance, and the like, and its practical value is extremely high.

Claims

The scope of the claims

1. The photoconductive layer formed on the conductive substrate is composed of (1) a reactive penyl erythritol compound or a reactive dipentyl erythritol compound.

90 to 40 mol% and (2) 100 to 100 parts by weight of a mixture of 100 to 60 mol% of the reactive phosphazene compound and (3) 0.1 to 50 parts by weight of the reactive siloxane compound An electrophotographic photoreceptor characterized by being covered with a protective layer comprising a composition.

2. An electrophotographic photosensitive member, wherein the photoconductive layer formed on the conductive substrate contains the composition according to claim 1.

3. An electrophotographic photoreceptor comprising: a charge generation layer and a charge transfer layer laminated on a conductive substrate; and the protective layer according to claim 1 formed as an outermost layer.

4. If the reactive pentaerythritol compound or reactive dipentae-risritol compound is — OCCH = CH ₂

Moshiku one OCC (CH ₃₎ = electrophotographic photoreceptor according to claim 1 comprising a CH ₂ organic group three or more.

5. The reactive phosphazene compound has the general formula (I)

[NP (A). (B) _b ] _B · ■ ■ (I)

[Wherein, A represents a curable group, B represents a non-curable group, and a and b represent real numbers satisfying a> 0, b≥0, and a + b = 2. N represents an integer of 3 or more. ]

The electrophotographic photoreceptor according to claim 1, wherein

6. The reactive siloxane compound

Wherein R ¹¹ and R ¹² each represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to ¹² carbon atoms, and Z ¹ and Z ² represent hydrogen or an organic residue, respectively. Is shown. M represents a positive integer. At least one of Z ¹ and Z ² is —O CCH 2 CH ₂ or — OCC (CH ₃ ) = CH ₂ . ]

Three

The electrophotographic 5 photoreceptor according to claim 1, wherein

7. The electrophotographic photosensitive member according to claim 1, wherein the photoconductive layer comprises a conductive substrate Z charge generation layer and a charge transfer layer.

8. The electrophotographic photosensitive member according to claim 1, wherein the photoconductive layer comprises a charge transfer layer and a charge transfer layer.