JP2942015B2 - Electrophotographic photoreceptor and electrophotographic apparatus using the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member having improved electrophotographic characteristics, and more particularly to an electrophotographic photosensitive member having a photosensitive layer containing a compound having a specific structure.

[0002]

2. Description of the Related Art In recent years, an organic electrophotographic photoreceptor containing an organic photoconductive compound as a main component has attracted attention in recent years because it has many advantages such as supplementing disadvantages of an inorganic photoreceptor such as film formability, plasticity and manufacturing cost. Many proposals have been made, some of which have been put to practical use.

As such an organic photoreceptor, poly-N
-An electrophotographic photoreceptor containing a photoconductive polymer represented by vinyl carbazole, a charge transfer complex formed from a Lewis acid such as 2,4,7-trinitro-9-fluorenone or the like as a main component has been proposed. I have.

[0004] These organic photoconductive polymers are superior to inorganic photoconductive polymers in terms of lightness, film-forming properties, and the like, but are inferior in terms of sensitivity, durability, stability against environmental changes, and the like. It was inferior to the conductive material and was not always satisfactory.

[0005] Subsequently, a function-separated electrophotographic photosensitive member in which the charge generation function and the charge transport function are respectively assigned to different substances brings about an improvement in sensitivity and durability, which have been regarded as disadvantages of the conventional organic photosensitive member. Was. Such a function-separated type photoreceptor has the advantage that the material selection range of the charge generating substance and the charge transporting substance is wide, and an electrophotographic photoreceptor having desired characteristics can be relatively easily produced. .

As the charge generating substance, azo pigments, polycyclic quinone pigments, cyanine dyes, squaric acid dyes and pyrylium salt dyes are known. Among them, many materials have been proposed and put into practical use from the viewpoint of high light fastness, high charge generation ability, and relatively easy material synthesis.

As the charge transport material, for example, Japanese Patent Publication No. Sho 52
No. 4188, pyrazoline compound, JP-B-55-4
Hydrazone compounds disclosed in JP-A-2380 and JP-A-55-52063, triphenylamine compounds disclosed in JP-B-58-32372 and JP-A-61-132950, and JP-A-54-151955 and JP-A-54-151955. A stilbene compound and the like disclosed in JP-A-58-198043 are known.

[0008] There are two types of charge transporting substances: a hole transporting substance and an electron transporting substance. The charge transporting substances described above and the charge transporting substances used in organic electrophotographic photoreceptors which have been put to practical use so far. Are mostly hole-transporting. A photoreceptor using a charge transporting substance having a hole transporting ability often has a conductive support, a charge generation layer, and a charge transporting layer in this order. Becomes If the polarity of the charging is negative, ozone is generated during the charging, and the ozone causes a problem that the photoreceptor is chemically deteriorated, and a-Se or a-Se is generated.
-Si has a drawback that it is inferior in durability to an inorganic photoreceptor such as Si.

As a countermeasure against the deterioration of the photoconductor due to ozone generated during charging, an electrophotographic photoconductor having a conductive support, a charge transport layer and a charge generation layer in this order, or an electron having a protective layer further provided on the photosensitive layer. Photosensitive members have been proposed, for example, in JP-A-61-75355 and JP-A-54-58445.

However, in the electrophotographic photoreceptor having such a layer structure, the charge generation layer having a relatively small thickness is the upper layer, and when the photoreceptor is repeatedly used, the characteristic deterioration due to abrasion of the photoreceptor surface is remarkable. In a photoreceptor provided with a protective layer for the purpose of solving the problem, since the protective layer is an insulating layer, the potential was not stabilized during repeated use, and stable characteristics could not be maintained.

Therefore, an invention of an organic electrophotographic photosensitive member having a conductive support, a charge generation layer and a charge transport layer in this order, and being usable by being charged with a positive electrode is expected. However, for this purpose, a charge transport material having an electron transport ability is required.
As a charge transport material having an electron transport ability, for example, 2,4,7-trinitro-9-fluorenone (T
NF) and dicyanomethylenefluorene carboxylate compounds as described in JP-A-61-148159 and JP-A-6-148159.
Anthraquinodimethane compounds such as JP-A-3-70257, JP-A-63-72664 and JP-A-63-104061;
4-Naphthoquinone compounds, diphenyldicyanoethylene compounds disclosed in JP-A-63-175860 and JP-A-63-174993 have been proposed.

Further, Japanese Patent Application Laid-Open No. 2-97953 discloses that
An electrophotographic photoreceptor having a charge generating layer containing a hole transporting charge generating material and a small amount of a dicyanovinyl compound having a specific structure has been proposed.

However, with the recent improvement in image quality, an electron capable of satisfying higher levels of sensitivity, potential characteristics, cost, and compatibility of the charge transport material with an organic solvent or a binder. Photoreceptors are being considered.

[0014]

SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photosensitive member having a photosensitive layer containing a charge transporting material having a novel structure.

An object of the present invention is to provide an electrophotographic photosensitive member having high sensitivity and capable of stably maintaining excellent electrophotographic characteristics when repeatedly used.

[0016]

That is, the present invention relates to an electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the photosensitive layer comprises a charge generating substance and the following formula (1).

[0017]

[Outside 50] (A represents an aromatic ring group derived from an aromatic compound having a reduction potential of −1.05 V or more, and R ¹ , R ² , R ³ ,
R ⁴ and R ⁵ represent a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aromatic ring group which may have a substituent, and R ¹ and R ² , R ³ , R ⁴ and R ⁵ may be the same or different. Where R ⁴ and R ⁵
Except that both are hydrogen atoms. n represents an integer of 0 or 1, and m represents an integer of 1 or 2. The present invention relates to an electrophotographic photoreceptor containing a charge transporting substance having an electron transporting ability represented by the formula (1).

Further, the present invention provides an electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the photosensitive layer comprises a charge generating substance and the following formulas (2) to (11), (13), (1)
An electrophotographic photoreceptor characterized by containing a charge transporting material having an electron transporting ability represented by a formula selected from the group consisting of 4) and (15). Equation (2)

[Outside 51] (Wherein, R _2-1 , R _2-2 , R _2-3 and R _2-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,

[Outside 52] Or

[Outside 53] And at least two or more of R _{2-1 to} R _2-4 are

[Outside 54] Or

[Outside 55] R _2-5 and R _2-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _2-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, and
2, r is an integer of 0 or 1, and R _2-6 and R _2-7 are directly linked to each other or linked via a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. May be formed. ) Equation (3)

[Outside 56] (Wherein, R _3-1 , R _3-2 , R _3-3 and R _3-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,

[Outside 57] Or

[Outside 58] And at least two or more of R _{3-1 to} R _3-4 are

[Outside 59] Or

[Outside 60] R _3-5 and R _3-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group; R _3-7 represents an alkyl group, an aralkyl group which may have a substituent, An aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, 2, and r are any integers of 0 and 1; _3-6 and R _3-7 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. )

[0019]

[0020]

Equation (4)

[0022]

[Outside 121] (Wherein, R _4-1 represents a thiophene ring group having a nitro group;
_4-2 and R _{4-3 each} represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, nitro Group, cyano group,

[0023]

[Outside 122] Or

[0024]

[Outside 123] And at least one of R _4-2 and R _4-3 is

[0025]

[Outside 124] Or

[0026]

[Outside 61] Wherein R _4-4 and R _{4-5 each} represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_4-6 is an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent. Wherein f and g are 1, 2, h is an integer of 0 or 1, and R _4-5 and R _4-6 are each directly or a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom, a sulfur They may be bonded via an atom to form a ring. ) Equation (5)

[Outside 62] (Wherein, R _5-1 , R _5-2 , R _5-3 , R _5-4 , R _5-5 and R
_5-6 is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,

[Outside 63] Or

[Outside 64] And at least two or more of R _{5-1 to} R _5-6 are

[Outside 65] Or

[Outside 66] Wherein R _5-7 and R _5-8 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_5-9 is an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent. And p and q are 0, 1, 2, and r are any integers of 0 and 1,
_5-8 and R _5-9 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom or sulfur atom to form a ring. ) Equation (6)

[Outside 67] (Wherein, R _6-1 , R _6-2 , R _6-3 , R _6-4 , R _6-5 and R
_6-6 is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,

[Outside 68] Or

[Outside 69] And at least two of R _{6-1 to} R _6-6 are

[Outside 70] Or

[Outside 71] R _6-7 and R _6-8 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _6-9 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, and
2, r is an integer of 0 or 1, and R _6-8 and R _6-9 are linked directly to each other or via a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. May be formed. ) Equation (7)

[Outside 72] (Wherein, R _7-1 , R _7-2 , R _7-3 and R _7-4 represent a hydrogen atom,
Halogen atom, alkyl group, aralkyl group, aromatic ring group,
-(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R _7-5
Or

[Outside 73] And at least two or more of R _{7-1 to} R _{7-4 are-}
(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R _7-5 or

[Outside 74] Wherein R _5-5 and R _7-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_7-7 represents an alkyl group, an aralkyl group, an aromatic ring group or a heterocyclic group, p and q are each an integer of 0, 1, 2, r is 0 or 1, and R _7-5 and R _{7 -7} may be linked to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom or sulfur atom to form a ring. ) Equation (8)

[Outside 75] (Wherein, R _8-1 , R _8-2 , R _8-3 and R _8-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _p -NO ₂ ,-( CH = C
H) _{q- R8-5} or

[Outside 76] Wherein at least two of R _{8-1 to} R _{8-4 are-} (CH = CH) _p -NO ₂ ,-(CH = CH) _q -R
_8-5 or

[Outside 77] Wherein R _8-5 and R _8-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_8-7 is an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent. And p and q are 0, 1, 2, and r are any integers of 0 and 1,
_8-6 and R _8-7 may be linked to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom or sulfur atom to form a ring. ) Equation (9)

[Outside 78] (Wherein, R _9-1 , R _9-2 , R _9-3 and R _9-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _f -NO ₂ ,-( CH = C
H) _g -R _9-5 or

[Outside 79] Wherein at least two or more of R _{9-1 to} R _{9-4 are-} (CH = CH) _f -NO ₂ ,-(CH = CH) _h -R
_9-5 or

[Outside 80] R _9-5 and R _{9-6 each} represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group; R _9-7 represents an alkyl group which may have a substituent; An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein i, f and g are 1, 2, and h are 0, 1 It is any integer, and R _9-6 and R _9-7 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. ) Equation (10)

[Outside 81] (Wherein, R _10-1 , R _10-2 , R _10-3 and R _10-4 are a hydrogen atom, a halogen atom, an alkyl group which may have a substituent,
An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _f -NO ₂ ,-(CH =
CH) _g -R _10-5 or

[Outer 82] Wherein at least two or more of R _{10-1 to} R _{10-4 are-} (CH = CH) _f -NO ₂ ,-(CH = CH) _g-
R _10-5 or

[Outside 83] R _10-5 and R _{10-6 each} represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group; R _10-7 represents an alkyl group having a substituent; an aralkyl group having a substituent; A substituent-containing aromatic ring group or a substituent-containing heterocyclic group; i, f, and g are 1, 2, and h are 0 or 1; Further, R _10-6 and R _10-7 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. )
Equation (11)

[Outside 84] (Wherein, R _11-1 and R _11-2 may have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, and a substituent. Aromatic ring group,
-(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R
_11-5 or

[Outside 85] Wherein at least one of R _11-1 and R _{11-2 is-} (CH = CH) _p -NO ₂ ,-(CH = CH)
_q -R _11-5 or

[Outside 86] R _11-5 and R _11-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _11-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, R _11-6 and R _11
11-7 may be formed by bonding rings directly to each other or through a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom, sulfur atom, etc., and R _11-3 and R _11-4 are a halogen atom, An alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, a heterocyclic group which may have a substituent, a nitro group or a cyano group And p and q are 0, 1, 2, and r is any integer of 0 or 1. ) Equation (13)

[Outside 87] (Wherein, R _13-1 , R _13-2 , R _13-3 and R _13-4 represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent,
An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _p -NO ₂ ,-(CH =
CH) _q -R _13-5 or

[Outside 88] And at least two or more of R _{13-1 to} R _{13-4 are-}
(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R _13-5
Or

[Outside 89] R _13-5 and R _13-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _13-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, and
2, r is an integer of 0 or 1, and R _13-6 and R _13-7 are bonded to each other directly or through a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. May be formed. ) Equation (14)

[Outside 90] (Wherein, R _14-1 , R _14-2 , R _14-3 and R _14-4 are a hydrogen atom, a halogen atom, an alkyl group which may have a substituent,
An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _f -NO ₂ ,-(CH =
CH) _g -R _14-5 or

[Outside 91] And at least two or more of R _{14-1 to} R _{14-4 are-
(CH = CH) f -NO 2} , - (CH = CH) g -R 14-5
Or

[Outside 92] R _14-5 and R _14-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _14-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein k, f and g are 1, 2, h are 0, 1 It is any integer, and R _14-6 and R _14-7 may combine with each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. ) The following equation (15)

[0027]

[Outside 93] (Wherein, R _15-1 , R _15-2 and R _15-3 represent-(CH ＝ C
_{H) s -NO 2, - (} CH = CH) t -R 15-4 or -
(CH = CH) _u -CH = _{CR 15-5} , s is 0,
1, t and u are any integers of 0 and 1, R _15-4 and R _15-5 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _15-6 is An alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent; X represents a divalent aromatic hydrocarbon ring group which may have a substituent or a residue necessary for forming a saturated hydrocarbon ring together with adjacent carbon atoms. )

[0028]

[0029]

[0030]

Further, the present invention is an electrophotographic apparatus using the above electrophotographic photosensitive member.

Preferred examples of the compound from which A of the formula (1) is derived are shown below together with their reduction potential (Ered), but are not limited thereto.

[0033]

[Outside 130]

[0034]

[Outside 131]

[0035]

[Outside 132]

However, the reduction potential was measured by the method described below.

(Method for Measuring Reduction Potential) A saturated calomel electrode was used as a reference electrode,

[0038]

[Outside 133] Using an acetonitrile solution, the potential of the working electrode was swept by a positive sweeper, and the peak position of the obtained current-potential curve was directly obtained as the value of the reduction potential of the compound.

More specifically, a sample

[0040]

[Outside 134] It is dissolved in an acetonitrile solution of an electrolytic solution to a concentration of about 5 to 10 mmol%. Then, a voltage is applied to the sample solution to change the potential from a high potential (OV) to a low potential (−1.5).
The current change when the voltage is linearly changed to V) is measured to obtain a current-potential curve. The value of the potential that reached the peak of the current value (highest potential side) in this current-potential curve was defined as the reduction potential in the present invention.

As preferred examples of the compound used in the present invention, the following formulas (2), (3), (5), (6),
(7), (8), (9), (10), (11), (1
Examples include compounds having the structures shown in 2), (13) and (14), but are not limited thereto.

[0042]

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[0086]

The halogen atom in the compound used in the present invention includes a fluorine atom, a chlorine atom and a bromine atom.
Alkyl groups such as methyl, ethyl, propyl, butyl, etc., aralkyl groups such as benzyl, phenethyl, naphthylmethyl, etc., aromatic ring groups such as phenyl, naphthyl, etc .; Groups such as furyl.

Examples of the substituent which may be present include an alkyl group such as methyl and ethyl, a halogen atom such as a fluorine atom and a chlorine atom, a cyano group and a nitro group.

Specific examples of the compound represented by the formula (1) are shown below, but it should not be construed that the invention is limited thereto.

[0090]

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[Outside 187]

Next, specific examples of the compounds represented by formulas (2) to (16) are shown below, but the present invention is not limited thereto.

As an illustrative method, first, the basic form is shown, and only the parts that change are described.

[0101]

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[Outside 335]

[0249]

[Outside 336]

[0250]

[Outside 337]

[0251]

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[0252]

[Outside 339]

[0253]

[Outside 340]

[0254]

[Outside 341]

[0255]

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[0256]

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[0257]

[Outside 344]

[0258]

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[0259]

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[0260]

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[0261]

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[0262]

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[0263]

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[0264]

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[0265]

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[0266]

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[0267]

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[0268]

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[0270]

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[0271]

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[0272]

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[0273]

[Outside 360]

[0274]

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[0275]

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[0276]

[Outside 363]

[0277]

[Outside 364]

[0278]

[Outside 365]

[0279]

[Outside 366]

[0280]

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[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

Examples of the synthesis of the compounds used in the present invention are shown below.

Synthesis Example 1 (Synthesis of Compound Example 1- (1)) 5 g of dimethyl diphenylmethylsulfonate and 3.5 g of 7-nitrofluorenone-2-aldehyde were dissolved in 60 ml of N, N-dimethylformamide (DMF). At room temperature, 1.77 g of sodium methoxide was slowly added. After completion of the addition, the mixture was stirred at room temperature for 1 hour, and further stirred for 3 hours while heating to about 50 ° C. with an aqueous solution. After allowing to cool, the crystals precipitated in water are collected by filtration, and recrystallized twice with a mixed solvent of toluene and methyl ethyl ketone, to give 1.9 of the desired compound.
g was obtained. Yield 37.2%.

Synthesis Example 2 (Synthesis of Compound Example 2- (3)) 0.81 g (14.9 mmol) of sodium methylate was added to 40 ml of DMF, and 3.90 g (14.27 g) of diethyl p-nitrobenzylphosphonate was added thereto. Mmol) / D
An MF 10 ml solution was slowly added dropwise at 20 to 25 ° C.
After completion of the dropwise addition, the mixture was stirred for 15 minutes, and then 2.04 g of 5-nitro-2-thiophenecarboxaldehyde was added.
A solution of (13.0 mmol) / 8 ml of DMF was slowly added dropwise at 25 ° C. or lower. After the completion of the dropwise addition, the mixture was stirred for 30 minutes as it was, and further heated and stirred for 2 hours at 40 to 50 ° C. in water. After cooling, the mixture was poured into 300 ml of a saturated saline solution, extracted with toluene, and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and separation and purification were performed using a silica gel column to obtain 2.45 g of the target compound. Yield 68%.

Synthesis Example 3 (Synthesis of Compound Example 3- (21))
0.76 g (14.0 mmol) of sodium methylate
Was added to 15 ml of DMF, and 3.25 g (11.9 mmol) of diethyl m-nitrobenzylphosphonate / D was added thereto.
A 20 ml solution of MF was slowly added dropwise at 20 to 25 ° C.
After dropping, stir for 15 minutes.

[0294]

[Outside 378] A solution of 2.0 g (7.0 mmol) in 40 ml of DMF was slowly added dropwise at 25 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 10 minutes as it was, and further heated and stirred for 2 hours at 50 to 60 ° C. in an oil solution. After cooling, the mixture was poured into 400 ml of methanol, and the precipitated crystals were collected by filtration.

The resulting crude crystals were further washed with methanol,
Recrystallization was performed several times with a mixed solvent of toluene and ethyl acetate to obtain 1.24 g of the target compound. Yield 44%.

Synthesis Example 4 (Synthesis of Compound Example 4- (17))
0.63 g (11.7 mmol) of sodium methylate
Was added to 15 ml of DMF, and 2.8 g (10.2 mmol) of diethyl o-nitrobenzylphosphonate / DM was added thereto.
A 15 ml solution of F was slowly added dropwise at 20 to 25 ° C. After dropping, stir for 15 minutes.

[0297]

[Outside 379] A solution of 1.5 g (6.4 mmol) in 10 ml of DMF was slowly added dropwise at 25 ° C. or lower. After completion of the dropping, the mixture was stirred for 15 minutes as it was, and further heated and stirred at 50 to 60 ° C. for 2 hours in an oil bath. After allowing to cool, the mixture was poured into 300 ml of methanol, and the precipitated crystals were collected by filtration.

The obtained crude crystals were further washed with methanol,
Recrystallization was performed several times with a mixed solvent of toluene and ethyl acetate to obtain 1.6 g of the desired compound. Yield 71%.

Synthesis Example 5 (Synthesis of Compound Example 5- (3)) 0.68 g (12.6 mmol) of sodium methylate was added to 10 ml of DMF, and 3.0 g (11.0 mmol) of diethyl p-nitrobenzylphosphonate was added thereto. Mmol) / DMF
A 10 ml solution was slowly added dropwise at 20-25 ° C. After dropping, stir for 15 minutes.

[0300]

[Outside 380] A solution of 2.0 g (7.0 mmol) in 15 ml of DMF was slowly added dropwise at 25 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 30 minutes as it was, and further heated and stirred in an oil bath at 50 to 60 ° C. for 2 hours. After cooling, pour into 300 ml of methanol,
The precipitated crystals were collected by filtration.

The obtained crude crystals were further washed with acetone and recrystallized several times with a mixed solvent of toluene and DMF to obtain 1.17 g of the desired compound. Yield 41%.

Synthesis Example 6 (Synthesis of Compound Example 6- (4)) 1.70 g (31.5 mmol) of sodium methylate was added to 15 ml of DMF, and 8.08 g of diethyl o-nitrobenzylphosphonate (29.6 g) was added thereto. Mmol) / DM
A 15 ml solution of F was slowly added dropwise at 20 to 25 ° C. After dropping, stir for 15 minutes.

[0303]

[Outside 381] A solution of 5.0 g (17.4 mmol) in 10 ml of DMF was slowly added dropwise at 20 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 15 minutes as it was, and further heated and stirred at 40 to 45 ° C. for 2 hours in an oil bath.

After cooling, the mixture was poured into 350 ml of methanol, and the precipitated crystals were collected by filtration. The obtained crude crystals were further washed with methanol and recrystallized several times with a mixed solvent of toluene and ethyl acetate to obtain 4.62 g of the desired compound. Yield 68%.

Synthesis Example 7 (Synthesis of Compound Example 7- (4)) 0.73 g (13.5 mmol) of sodium methylate was added to 10 ml of DMF, and 3.35 g (12.3) of diethyl o-nitrobenzylphosphonate was added thereto. Mmol) / DM
A 15 ml solution of F was slowly added dropwise at 20 to 25 ° C. After dropping, stir for 30 minutes,

[0306]

[Outside 382] A solution of 2.0 g (6.8 mmol) in 20 ml of DMF was slowly added dropwise at 25 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 10 minutes as it was, and further heated and stirred at 50 to 60 ° C. for 2 hours in an oil bath. After allowing to cool, the mixture was poured into 300 ml of methanol, and the precipitated crystals were collected by filtration.

The resulting crude crystals were further washed with methanol,
Recrystallization was performed several times with a mixed solvent of toluene and ethyl acetate to obtain 1.19 g of the desired compound. Yield 42.4%.

Synthesis Example 8 (Synthesis of Compound Example 8- (4)) 1.0 g (18.5 mmol) of sodium methylate was added to D
MF (15 ml), and m-nitrobenzyl phosphonate diethyl 4.36 g (16.0 mmol) / DMF
A 20 ml solution was slowly added dropwise at 20-25 ° C. After dropping, stir for 20 minutes,

[0309]

[Outside 383] A solution of 2.0 g (9.4 mmol) in 40 ml of DMF was slowly added dropwise at 25 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 10 minutes as it was, and further heated and stirred in an oil bath at 50 to 60 ° C. for 3 hours. After cooling, the mixture was poured into 500 ml of methanol, and the precipitated crystals were collected by filtration.

The obtained crude crystals were further washed with methanol,
Recrystallization was performed several times with a mixed solvent of toluene and ethyl acetate to obtain 1.2 g of the desired compound. Yield 38.5 g.

Synthesis Example 9 (Synthesis of Compound Example 9- (24))
2.6 g (48.1 mmol) of sodium methylate were added to 15 ml of DMF, and 11.0 g (40.3 mmol) of diethyl m-nitrobenzylphosphonate / DM was added thereto.
A 30 ml solution of F was slowly added dropwise at 20 to 25 ° C. After dropping, stir for 30 minutes,

[0312]

[Outside 384] A solution of 3.0 g (13.5 mmol) in 15 ml of DMF was slowly added dropwise at 30 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 10 minutes as it was, and further heated and stirred in an oil bath at 50 to 55 ° C. for 2 hours.

After cooling, the mixture was poured into 250 ml of methanol, and the precipitated crystals were collected by filtration. The obtained crude crystals were further washed with methanol and recrystallized several times with a mixed solvent of toluene and ethyl acetate to obtain 4.2 g of the desired compound. Yield 67.6%.

Synthesis Example 10 (Synthesis of Compound Example 10- (21)) 1.4 g (25.9 mmol) of sodium methylate was added to 15 ml of DMF, and 6.2 g of diethyl m-nitrobenzylphosphonate (22.7 g) was added thereto. Mmol) /
A 30 ml solution of DMF was slowly added dropwise at 20 to 25 ° C. After dropping, stir for 20 minutes,

[0315]

[Outside 385] A solution of 2.0 g (8.1 mmol) in 30 ml of DMF was slowly added dropwise at 25 ° C. or lower. After the dropwise addition, the mixture was stirred for 15 minutes as it was, and further heated and stirred at 60 to 70 ° C. for 3 hours in an oil bath.

After cooling, the mixture was poured into 500 ml of methanol, and the precipitated crystals were collected by filtration. The obtained crude crystals were further washed with methanol and recrystallized several times with a mixed solvent of toluene and ethyl acetate to obtain 1.87 g of the desired compound. Yield 47.4%.

Synthesis Example 11 (Synthesis of Compound Example 11- (21)) 1.25 g (23.1 mmol) of sodium methylate was added to 15 ml of DMF, and 4.71 g (17.2 g) of diethyl p-nitrobenzylphosphonate was added thereto. Mmol)
/ DMF 15 ml solution was slowly added dropwise at 20-25 ° C. After dropping, stir for 30 minutes,

[0318]

[Outside 386] A solution of 3.0 g (11.5 mmol) in 25 ml of DMF was slowly added dropwise at 25 ° C. or lower. After the completion of the dropwise addition, the mixture was stirred for 20 minutes as it was, and further heated and stirred in an oil bath at 60 to 65 ° C for 3 hours.

After cooling, the mixture was poured into 300 ml of methanol, and the precipitated crystals were collected by filtration. The obtained crude crystals were further washed with methanol and recrystallized several times with a mixed solvent of toluene and ethyl acetate to obtain 1.66 g of the desired compound. Yield 38%.

[0320]

[0321]

[0322]

Synthesis Example 13 (Synthesis of Compound Example 13- (4)) 0.62 g (11.5 mmol) of sodium methylate was added to 10 ml of DMF, and 2.6 g of diethyl o-nitrobenzylphosphonate (9.5 g) was added thereto. Mmol) / D
A MF (15 ml) solution was slowly added dropwise at 20 to 25 ° C.
After dropping, stir for 10 minutes,

[0324]

[Outside 388] A solution of 1.5 g (5.7 mmol) in 20 ml of DMF was slowly added dropwise at 25 ° C. or lower. After the completion of the dropwise addition, the mixture was stirred for 10 minutes, and then heated and stirred in an oil bath at 50 to 60 ° C. for 2 hours. After cooling, pour into 300 ml of methanol,
The precipitated crystals were collected by filtration.

The obtained crude crystals were further washed with methanol,
Recrystallization was performed several times with a mixed solvent of toluene and ethyl acetate to obtain 1.1 g of the desired compound. Yield 50%.

Synthesis Example 14 (Synthesis of Compound Example 14- (20)) 3.6 g (66.6 mmol) of sodium methylate was added to 30 ml of DMF, and 13.2 g of diethyl p-nitrobenzylphosphonate (48 g) was added thereto. 3 mmol)
/ DMF 45 ml solution was slowly added dropwise at 20-25 ° C. After dropping, stir for 30 minutes,

[0327]

[Outside 389] A solution of 5.0 g (16.8 mmol) in 40 ml of DMF was slowly added dropwise at 30 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 10 minutes as it was, and further heated and stirred at 50 to 60 ° C. for 2 hours in an oil bath.

After cooling, the mixture was poured into 500 ml of methanol, and the precipitated crystals were collected by filtration. The obtained crude crystals were further washed with methanol and recrystallized several times with a mixed solvent of toluene and ethyl acetate to obtain 4.3 g of the desired compound. Yield 47.7%.

Synthesis Example 15 (Synthesis of Compound Example 15- (14)) 0.57 g (10.6 mmol) of sodium methylate was added to 20 ml of DMF, and 2.45 g (9.0 of diethyl m-nitribenzylphosphonate) was added thereto. Mmol) /
A solution of 10 ml of DMF was slowly added dropwise at 20 to 25 ° C. After dropping, stir for 30 minutes,

[0330]

[Outside 390] A solution of 2.0 g (5.3 mmol) in 15 ml of DMF was slowly added dropwise at 25 ° C. or lower. After completion of the dropwise addition, the mixture was stirred for 15 minutes as it was, and further heated and stirred at 60 to 70 ° C. for 2 hours in an oil bath.

After allowing to cool, the mixture was poured into 300 ml of methanol, and the precipitated crystals were collected by filtration. The obtained crude crystals were further washed with methanol and recrystallized several times with a mixed solvent of toluene and ethyl acetate to obtain 1.1 g of the desired compound. Yield 41.9%.

[0332]

Other compounds can be synthesized by the same method, but are not limited to these methods.

The electrophotographic photoreceptor of the present invention has a photosensitive layer on a conductive support. Examples of the constitution of the photosensitive layer include the following. However, (1), (2) and (4) are in the order of lower layer / upper layer. (1) layer containing charge generating material / layer containing charge transporting material (2) layer containing charge transporting material / layer containing charge generating material (3) layer containing charge generating material and charge transporting material (4) Layer containing charge generating substance / layer containing charge generating substance and charge transporting substance The compound having a high transporting ability for the compound used in the present invention represented by the above-mentioned ones, and the form of the photosensitive layer is ( In the case of 1), it is preferable to use for positive charging, and in the case of (2), it is preferable to use for negative charging. In the cases of (3) and (4), both positive and negative charging can be used.

Of course, the structure of the electrophotographic photosensitive member of the present invention is not limited to the above basic structure.

The form of the photosensitive layer in the invention is particularly preferably the form (1), which will be described in more detail below.

The charge generating substance used in the present invention may be any substance as long as it has a charge generating ability.
For example, the following substances may be mentioned. (1) Azo pigments such as monoazo, bisazo and trisazo (2)
Phthalocyanine pigments such as metal phthalocyanine and non-metal phthalocyanine (3) indigo pigments such as indigo and thioindigo (4) perylene pigments such as perylene anhydride and berylenimide (5) polycyclic quinones such as anthraquinone and pyrenequinone Pigments (6) squarium dyes (7) pyrylium salts and thiopyrylium salts (8) triphenylmethane dyes (9) inorganic substances such as selenium and amorphous silicon

These charge generating substances may be used alone or in combination of two or more.

The layer containing the charge generating substance, that is, the charge generating layer is formed by dispersing the above-described charge generating substance in an appropriate binder and applying the resultant onto a conductive support. Can be. Further, it can also be formed by forming a thin film on a conductive support by a dry method such as evaporation, sputtering, or CVD.

The binder can be selected from a wide range of binder resins, for example, polycarbonate, polyester, polyarylate, butyral resin, polystyrene,
Polyvinyl acetal, diallyl phthalate resin, acrylic resin, methacrylic resin, vinyl acetate resin, phenolic resin, silicone resin, polysulfone, styrene-butadiene copolymer, alkyd resin, epoxy resin, urea resin, vinyl chloride-vinyl acetate copolymer, etc. But are not limited to these.

These resins may be used alone, as a copolymer of each component, or as a mixture of two or more resins.

The amount of the resin contained in the charge generation layer is preferably 80% by weight or less based on the total weight of the layer, and more preferably 40% by weight.

The thickness of the charge generation layer is preferably 5 μm or less, particularly preferably 0.01 to 2 μm.

Furthermore, various sensitizers may be added to the charge generation layer.

The layer containing the charge transporting substance, that is, the charge transporting layer, can be formed by combining with an appropriate binder resin used in the present invention.

The compounds of the present invention can be used alone or in combination of two or more. Further, other charge transporting substances can be used in combination.

As the binder resin used for the charge transport layer, in addition to those used for the charge generation layer, photoconductive polymers such as polyvinyl carbazole and polyvinyl anthracene can be further used.

The compounding ratio of the binder resin to the compound used in the present invention is preferably 10 to 500 parts by weight per 100 parts by weight of the binder.

The charge transport layer has a thickness of 5 to 40 μm, particularly 1 to 40 μm.
The range of 0 to 30 μm is preferred.

Further, an antioxidant, an ultraviolet absorber or a plasticizer may be added to the charge transport layer as required.

When the photosensitive layer has the structure of (3), that is, when the photosensitive layer is a single layer, the coating solution prepared by dispersing and dissolving the above-mentioned charge generating substance and the compound used in the present invention in the above-mentioned suitable binder is used. It is formed by coating and drying. At this time, the film thickness is 5 to 5.
40 μm is preferable, and particularly preferably 10 to 30 μm.

In the present invention, a layer having a barrier function and an adhesive function, that is, a so-called undercoat layer may be provided between the conductive support and the photosensitive layer.

Examples of the material of the undercoat layer include polyvinyl alcohol, polyethylene oxide, ethyl cellulose, methyl cellulose, casein, polyamide, glue, gelatin and the like.

These are dissolved in an appropriate solvent and coated on a conductive support. The film thickness is 5 μm or less, especially 0.2 μm.
~ 3.0 µm is preferred.

Further, in the present invention, a resin layer or a resin layer in which a conductive substance is dispersed can be provided on the photosensitive layer in order to protect the photosensitive layer from various mechanical and electrical external forces.

The various layers described above are formed on a conductive support by a coating method such as dip coating, spray coating, spinner coating, roller coating, Meyer bar coating, or blade coating using an appropriate organic solvent. Can be formed.

As the conductive support in the present invention, the following forms can be exemplified.
(1) Aluminum, aluminum alloy, stainless steel,
Plates or drums made of metal such as copper.
(2) Aluminum, palladium, etc. on a non-conductive support such as glass, resin, paper or the conductive support of the above (1).
A film formed by depositing or laminating a metal such as rhodium, gold, or platinum. (3) Depositing or applying a layer of a conductive compound such as a conductive polymer, tin oxide, or indium oxide on a non-conductive support such as glass, resin, paper, or the conductive support of (1). What was formed by

The electrophotographic photoreceptor of the present invention can be widely used not only for electrophotographic copying machines but also for electrophotographic applications such as facsimile machines, laser printers, CRT printers, and electrophotographic plate making systems.

FIG. 1 shows a schematic configuration example of a general transfer type electrophotographic apparatus using the electrophotographic photosensitive member of the present invention.

In the figure, reference numeral 1 denotes a drum type photosensitive member as an image bearing member, which is driven to rotate around an axis 1a in a direction indicated by an arrow at a predetermined peripheral speed. The photoreceptor 1 is uniformly charged with a predetermined positive or negative potential on its peripheral surface by a charging means 2 during the rotation process, and then, in an exposure section 3, a light image exposure L (slit exposure / Laser beam operation exposure etc.). As a result, an electrostatic latent image corresponding to the exposure image is sequentially formed on the peripheral surface of the photoconductor.

The electrostatic latent image is then developed with toner by developing means 4, and the developed toner image is transferred by transfer means 5 between the photosensitive member 1 and the transfer means 5 from a paper feeding unit (not shown). The transfer material P is sequentially transferred onto the surface of the transfer material P which has been synchronized and fed.

The transfer material P having undergone the image transfer is separated from the photoreceptor surface, introduced into the image fixing means 8 and subjected to image fixing to be printed out as a copy out of the apparatus.

The surface of the photoreceptor 1 after the image transfer is cleaned and cleaned by removing the untransferred toner by the cleaning means 6, and is further subjected to a charge removal treatment by the pre-exposure means 7 to be used repeatedly for image formation.

As the uniform charging means 2 for the photosensitive member 1, a corona charging device is generally widely used. Transfer device 5
Also, corona transfer means are generally widely used. As an electrophotographic apparatus, a plurality of components such as the above-described photoreceptor, developing means, and cleaning means are integrally connected as an apparatus unit, and this unit is configured to be detachable from the apparatus body. You may. For example, a unit is formed by integrally supporting at least one of the charging unit, the developing unit, and the cleaning unit together with the photoreceptor, and the unit is detachably attached to the apparatus main body. You may make it a detachable structure. At this time, the above-described device unit may be provided with a charging unit and / or a developing unit.

In the case where the electrophotographic apparatus is used as a copying machine or a printer, the light image exposure L involves irradiating the photosensitive member with reflected light or transmitted light from the original, or reading the original with a sensor and converting it into a signal. According to this signal, scanning of a laser beam, driving of an LED array, or driving of a liquid crystal shutter array is performed to irradiate light to a photoconductor.

When used as a facsimile printer, the light image exposure L is an exposure for printing received data. FIG. 2 is a block diagram showing an example of this case.

[0367] The controller 11 controls the image reading unit 10 and the printer 19. The whole controller 11 is CP
It is controlled by U17. The read data from the image reading unit is transmitted to the partner station through the transmission circuit 13. Data received from the partner station is sent to the printer 19 through the receiving circuit 12. The printer controller 18 controls a printer 19. 14 is a telephone.

The image received from the line 15 (image information from a remote terminal connected via the line) is demodulated by the receiving circuit 12, and then the CPU 17 performs a composite processing of the image information and sequentially stores the image information in the image memory 16. Is stored. Then, when the image of at least one page is stored in the memory 16,
The image information of the page is performed. The CPU 17 is a memory 1
6, one page of image information is read out and the combined one-page image information is sent to the printer controller 18. The printer controller 18 receives 1
When the image information of the page is received, the printer 19 is controlled to record the image information of the page.

The CPU 17 receives the next page during recording by the printer 19.

As described above, the image is received and recorded.

[0371]

EXAMPLES Example 1 JP-A-61-239248 (USP: 4,72)
8,592) with a solution prepared by dissolving 4 g of oxytitanium phthalocyanine obtained in accordance with the production example disclosed in 2 g of polyvinyl butyral resin (butyralization degree: 70 mol%, weight average molecular weight: 50,000) in 90 ml of cyclohexanone for 20 hours using a sand mill. It was dispersed to prepare a coating liquid.

After diluting this coating liquid, an aluminum sheet was
Coating was performed with a Meyer bar so that the film thickness after drying was 0.2 μm, to prepare a charge generation layer.

Next, Compound Example 1 was used as a charge transport material.
(9) 5 g of a polycarbonate resin (weight average molecular weight 4
(000) 5 g of monochlorobenzene (50 parts by weight)
-N, N-dimethylformamide (50 parts by weight) solution 4
The solution was dissolved in 0 g, and this solution was applied on the above-mentioned charge generating layer with a Meyer bar, and a charge transport layer having a dry film thickness of 15 μm was provided to prepare an electrophotographic photosensitive member.

The electrophotographic photosensitive member thus produced was corona-charged at +6 KV in a static manner using an electrostatic copying paper tester EPA-8100 manufactured by Kawaguchi Electric Co., Ltd., and was held in a dark place for 1 second. Exposure was performed at an illuminance of 20 Lux, and charging characteristics were examined.

As the charging characteristics, the surface potential (V ₀ )
Exposure (E
Potential after irradiation with light amount of _1/2) and 100 Lux · sec, i.e. residual potential (V _R) was measured.

Further, in order to evaluate the durability against repeated use, the photosensitive member prepared above was attached to a photosensitive drum cylinder of a copying machine NP-6650 manufactured by Canon Inc., and a modified machine of the same was used. performed 1,000 sheet copying were measured initial and the light portion potential after 1,000 sheet copying (V _L) and the dark potential (V _D). The initial V _D and V _L are each +
650 V and +150 V were set. The results are shown in Table 1 below.

[0377]

[Table 1]

Examples 2 to 10 Compound examples 1- (3), 1- (6), 1- (10) and 1- (1) were used instead of compound example 1- (9) as the charge transporting substance.
1), 1- (13), 1- (21), 1- (29), 1
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1 except that-(36) and 1- (43) were used.

The results are shown in Table 2.

Comparative Examples 1 to 6 Electrophotographic photosensitive members were prepared in the same manner using the following compounds as charge transporting substances, and measured.

The results are shown in Table 3.

[0382]

[Outside 391]

[0383]

[Outside 392]

[0384]

[Table 2]

[0385]

[Table 3]

Example 11 A polyvinyl butyral resin having a weight average molecular weight of 40,0
00, 95 ml of cyclohexanone, 24 hours of dispersion time, Compound Example 2- (4) as the charge transport material, 35,000 weight average molecular weight of the polycarbonate resin, 6 g of the used amount, and chlorobenzene as the solvent for the charge transport layer. 1
An electrophotographic photosensitive member was produced in the same manner as in Example 1 except that the amount was changed to 00 g. However, the thickness of the charge generation layer is 0.4 μm
The thickness of the charge transport layer was 17 μm.

The obtained photosensitive member was evaluated in the same manner as in Example 1. However, 2,000 copies were made.

Table 4 shows the results.

[0389]

[Table 4]

Examples 12 to 20 and Comparative Examples 7 to 10 Compound examples 2- (1), 2- (11), 2- (12), 2- (12) were used instead of compound example 2- (4) as the charge transporting substance.
(22), 2- (23), 2- (37), 2- (4
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 11 except that 5), 2- (70) and 2- (61) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transporting substance.

The results are shown in Table 5.

[0393]

[Outside 393]

[0394]

[Table 5]

[0395]

[Table 6]

Example 21 An electrophotographic photosensitive member was prepared in the same manner as in Example 11, except that the charge transporting material was Compound Example 3- (8) and the weight average molecular weight of the polycarbonate resin was 80,000. However, the thickness of the charge transport layer was 20 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 6.

[0399]

[Table 7]

Examples 22 to 30, Comparative Examples 11 and 12 Compounds 3- (3), 3- (15), 3- (29), and 3- (3) were substituted for compound 3- (8) as the charge transporting substance. 3
3), 3- (45), 3- (58), 3- (60), 3
Example 21 except for using-(69) and 3- (78)
An electrophotographic photoreceptor was prepared in the same manner as described above and evaluated.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

The results are shown in Table 7.

[0403]

[Outside 394]

[0404]

[Table 8]

[0405]

[Table 9]

Example 31 The weight average molecular weight of polyvinyl butyral resin was 80,00
0, the dispersion time was 10 hours, and the charge transport material was Compound Example 4-
An electrophotographic photosensitive member was prepared in the same manner as in Example 11, except that the weight average molecular weight of (4) and the polycarbonate resin was changed to 50,000. However, the thickness of the charge transport layer is 19
μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 8.

[0409]

[Table 10]

Examples 32 to 40 and Comparative Examples 13 and 14 Instead of Compound Example 4- (4) as a charge transport material, Compound Examples 4- (3), 4- (8), 4- (9), 4- (9) (1
3), 4- (18), 4- (21), 4- (27), 4
Example 31 except for using-(29) and 4- (37)
An electrophotographic photoreceptor was prepared in the same manner as described above and evaluated.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transporting substance.

The results are shown in Table 9.

[0413]

[Outside 395]

[0414]

[Table 11]

[0415]

[Table 12]

Example 41 A polyvinyl butyral resin having a weight average molecular weight of 100
An electrophotographic photoreceptor was prepared in the same manner as in Example 11, except that the dispersion time was set at 000 for 10 hours and the charge transport material was changed to Compound Example 5- (48). However, the thickness of the charge generation layer was 0.2 μm, and the thickness of the charge transport layer was 20 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 10.

[0419]

[Table 13]

Examples 42 to 50 and Comparative Examples 15 and 16 Instead of Compound Example 5- (48) as a charge transport material, Compound Examples 5- (7), 5- (12), 5- (19), 5- (19)
(23), 5- (29), 5- (66), 5- (8
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 41 except that 5), 5- (111) and 5- (114) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

The results are shown in Table 11.

[0423]

[Outside 396]

[0424]

[Table 14]

[0425]

[Table 15]

Example 51 The compound of Example 6- (91) was used as the charge transporting material, and the amount of the compound was 6
g and the weight average molecular weight of the polycarbonate resin is 5
An electrophotographic photoreceptor was prepared in the same manner as in Example 11 except that the amount was set to 000. However, the thickness of the charge generation layer is 0.2
μm, and the thickness of the charge transport layer was 19 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 12.

[0429]

[Table 16]

Examples 52 to 60, Comparative Examples 17 and 18 Compounds 6- (5), 6- (27), 6- (39) and 6- (39) as charge-transporting substances were substituted for compound example 6- (91).
(49), 6- (60), 6- (65), 6- (7
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 51 except that 0), 6- (77) and 6- (82) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

Table 13 shows the results.

[0433]

[Outside 397]

[0434]

[Table 17]

[0435]

[Table 18]

Example 61 A polyvinyl butyral resin having a weight average molecular weight of 50,0
00, a dispersion time of 20 hours, and a charge transport material of compound 7-
An electrophotographic photosensitive member was prepared in the same manner as in Example 11, except that the weight average molecular weight of (3) and the polycarbonate resin was changed to 50,000. However, the thickness of the charge generation layer is 0.1.
3 μm, and the thickness of the charge transport layer was 18 μm.

The obtained photosensitive member was evaluated in the same manner as in Example 11.

The results are shown in Table 14.

[0439]

[Table 19]

Examples 62 to 70, Comparative Examples 19 and 20 Instead of Compound Example 7- (3) as a charge transport material, Compound Examples 7- (5), 7- (13), 7- (26), 7-
(32), 7- (48), 7- (59), 7- (6
8), an electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 61 except that 7- (78) and 7- (84) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport compound.

The results are shown in Table 15.

[0443]

[Outside 398]

[0444]

[Table 20]

[0445]

[Table 21]

Example 71 A polyvinyl butyral resin having a weight average molecular weight of 30,0
An electrophotographic photoreceptor was prepared in the same manner as in Example 11, except that the charge transporting material was Compound Example 8- (11) and the weight average molecular weight of the polyvinyl butyral resin was 55,000.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 16.

[0449]

[Table 22]

Examples 72 to 80, Comparative Examples 21 and 22 Compound examples 8- (9), 8- (14), 8- (21), and 8-- as charge-transporting substances instead of compound example 8- (11).
(26), 8- (30), 8- (61), 8- (6
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 71 except that 3), 8- (66) and 8- (69) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

The results are shown in Table 17.

[0453]

[Outside 399]

[0454]

[Table 23]

[0455]

[Table 24]

Example 81 A polyvinyl butyral resin having a weight average molecular weight of 50,0
00, a dispersion time of 20 hours, and a charge transport material of Compound Example 9.
-(6) and the weight average molecular weight of the polycarbonate is 6
An electrophotographic photoreceptor was prepared in the same manner as in Example 11 except that the amount was set to 000. However, the thickness of the charge generation layer is 0.5
μm, and the thickness of the charge transport layer was 19 μm.

The results are shown in Table 18.

[0458]

[Table 25]

Examples 82 to 90, Comparative Examples 23 and 24 Instead of Compound Example 9- (6) as a charge transport material, Compound Examples 9- (5), 9- (23), 9- (29), 9-
(35), 9- (57), 9- (71), 9- (7
6), 9- (85) and 9- (91) were used to prepare and evaluate an electrophotographic photosensitive member in the same manner as in Example 81 except that 9- (91) was used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

Table 19 shows the results.

[0462]

[Outside 400]

[0463]

[Table 26]

[0464]

[Table 27]

Example 91 An electrophotographic photosensitive member was prepared in the same manner as in Example 11, except that the amount of oxytitanium phthaloanine used was 6 g and the charge transporting substance was Compound Example 10- (6). However, the thickness of the charge generation layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

Table 20 shows the results.

[0468]

[Table 28]

Examples 92 to 100, Comparative Examples 25 and 2
6. Compound examples 10- (1), 10- (8), 10- (13) instead of compound example 10- (6) as charge transport materials
10- (19), 10- (27), 10- (39), 1
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 91 except that 0- (55), 10- (73) and 10- (87) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

The results are shown in Table 21.

[0472]

[Outside 401]

[0473]

[Table 29]

[0474]

[Table 30]

Example 101 A polyvinyl butyral resin having a weight average molecular weight of 80,0
An electrophotographic photoreceptor was prepared in the same manner as in Example 11, except that the 00 charge transport material was Compound Example 11- (2) and the weight average molecular weight of the polycarbonate resin was 50,000. However, the thickness of the charge generation layer was 0.5 μm, and the thickness of the charge transport layer was 19 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 22.

[0478]

[Table 31]

Examples 102 to 110, Comparative Examples 27 and 29 Compounds 11- (3), 11- (5), 11- (9), and 1- (3) as charge-transporting substances were substituted for compound example 11- (2).
1- (11), 11- (14), 11- (17), 11
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 101 except that-(24), 11- (27) and 11- (30) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transporting substance.

Table 23 shows the results.

[0482]

[Outside 402]

[0483]

[Table 32]

[0484]

[Table 33]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0490]

[0492]

[0493]

[0494]

Example 121 The degree of butyralization of polyvinyl butyral was 74 mol.
%, The weight average molecular weight was 60,000. An electrophotographic photoreceptor was produced in the same manner as in Example 11, except that the charge transport material was Compound Example 13- (4) and the weight average molecular weight of the polycarbonate resin was 100,000. . However, the thickness of the charge generation layer was 0.2 μm, and the thickness of the charge transport layer was 20 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

The results are shown in Table 26.

[0498]

[Table 37]

Examples 122 to 130, Comparative Examples 33 and 34 Compound examples 13- (9), 13- (11) and 13- (1) were used instead of compound example 13- (4) as the charge transporting substance.
5), 13- (25), 13- (50), 13- (5
2), 12- (57), 13- (61) and 13-
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 121 except that (65) was used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transporting substance.

[0501] The results are shown in Table 27.

[0502]

[Outside 404]

[0503]

[Table 38]

[0504]

[Table 39]

Example 131 A compound was prepared in the same manner as in Compound 14- (28), except that the charge transporting material was Compound Example 14- (28).
An electrophotographic photosensitive member was produced in the same manner as in Example 11. However, the thickness of the charge generation layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 11.

Table 28 shows the results.

[0508]

[Table 40]

Examples 132 to 140, Comparative Examples 35 and 36 Instead of Compound Example 14- (28) as a charge transporting compound, Compound Examples 14- (9), 14- (22), 14- (3
3), 14- (42), 14- (49), 14- (5
3), 14- (59), 14- (74) and 14-
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 131 except that (89) was used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transport material.

[0511] The results are shown in Table 29.

[0512]

[Outside 405]

[0513]

[Table 41]

[0514]

[Table 42]

Example 141 The degree of butyralization of polyvinyl butyral resin was 68 mo.
An electrophotographic photoreceptor was prepared in the same manner as in Example 11, except that the weight-average molecular weight was 35,000, the charge-transporting substance was Compound Example 15- (8), and the weight-average molecular weight of the polycarbonate resin was 25,000. did. However, the thickness of the charge generation layer was 0.2 μm, and the thickness of the charge transport layer was 18 μm.

The obtained photosensitive member was evaluated in the same manner as in Example 11.

The results are shown in Table 30.

[0518]

[Table 43]

Examples 142-150 and Comparative Examples 37-39 Instead of Compound Example 15- (8) as a charge transporting substance, Compound Examples 15- (2), 15- (5), 15- (16),
15- (21), 15- (28), 15- (31), 1
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 141 except that 5- (44), 15- (57) and 15- (86) were used.

For comparison, an electrophotographic photosensitive member was prepared and evaluated in the same manner except that the following comparative compound was used as a charge transporting substance.

Table 31 shows the results.

[0522]

[Outside 406]

[0523]

[Table 44]

[0524]

[Table 45]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

Example 163 5 g of N-methoxymethylated 6 nylon resin (weight average molecular weight: 150,000) and 5 g of alcohol-soluble copolymerized nylon resin (weight average molecular weight: 100,0
00) A solution prepared by dissolving 5 g in 90 g of methanol was applied by a Meyer bar, and an undercoat layer having a thickness of 1 μm after drying was provided. Then the following formula

[0536]

[Outside 408] 1 g of a charge-generating substance represented by the following formula: polyvinyl butyral resin (butyralization degree: 70%, weight average molecular weight: 50,000)
0) 0.5 g and 50 g of dioxane were dispersed by a ball mill disperser for 30 hours. After this dispersion is diluted, it is applied on the undercoat layer manufactured previously by a blade coating method,
A charge generation layer having a thickness of 0.15 μm after drying was formed.

Next, Compound Example 1 was used as a charge transport material.
(38) 10 g and 15 g of polymethyl methacrylate resin (weight average molecular weight: 70,000) are dissolved in 100 g of monochlorobenzene, applied on the previously formed charge generating layer by a blade coating method, and dried to have a thickness of 14 μm.
m of the charge transport layer was formed.

The photoreceptor thus produced was charged with +6 KV
Was performed, and the surface potential (V ₀ ) at this time was measured. Further, the surface potential (V ₁ ) after the photosensitive member was left in a dark place for 1 second and darkly attenuated was measured. The sensitivity of the V ₁ 1/2
It was evaluated by measuring the exposure amount (E _1/2 ) required to attenuate the sample. Further, a residual potential of 100 (μJ /
cm ² ) of the laser light intensity was measured. At this time, a gallium / aluminum / arsenic ternary semiconductor laser (output: 5 mW; oscillation wavelength 780) was used as a light source.
nm).

Next, an actual image forming test was performed by attaching the above-mentioned photosensitive member to a remodeled machine of Canon NP-9330, which is a digital copier of the reversal development system equipped with the same semiconductor laser as described above. Surface potential after primary charging; +600 V, surface potential after image exposure; +100 V (exposure amount: 2.0 μJ / cm ² ), initial and 1000
Characters and images after copying were evaluated visually.

The results are shown in Table 34.

Example 164 The weight average molecular weight of N-methoxymethylated 6 nylon resin was 200,000, the weight average molecular weight of alcohol-soluble copolymerized nylon resin was 80,000, and methanol was 10
0 g, the weight average molecular weight of the polyvinyl butyral resin is 1
00,000, the amount used is 0.7 g, the dispersion time is 20
Time, the charge transport material was Compound Example 2- (18), and the weight average molecular weight of the polymethyl methacrylate resin was 80,000.
An electrophotographic photoreceptor was produced in the same manner as in Example 163 except that the amount used was 10 g. However, the thickness of the charge generation layer was 0.2 μm, and the thickness of the charge transport layer was 13 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 163. However, the number of copies was 5000.

The results are shown in Table 34.

Example 165 The weight average molecular weight of N-methoxymethylated 6 nylon resin was 100,000, the amount of polyvinyl butyral resin used was 1 g, and the charge transporting material was Compound Example 3- (16) and the weight of polymethyl methacrylate resin. Average molecular weight 40,
An electrophotographic photosensitive member was produced in the same manner as in Example 164 except that the value was changed to 000. However, the thickness of the undercoat layer is 0.5 μm.
m, the thickness of the charge generation layer was 0.3 μm, and the thickness of the charge transport layer was 16 μm.

The potential characteristics and the image of the obtained photoreceptor were evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation was 3.8 (μJ / cm ² ).

The results are shown in Table 34.

Example 166 The weight average molecular weight of N-methoxymethylated 6 nylon resin was 100,000, the weight average molecular weight of polyvinyl butyral resin was 150,000, and the charge transport material was Compound Example 4.
Example 164 except that the weight average molecular weight of-(18) and the polymethyl methacrylate resin was 100,000.
An electrophotographic photoreceptor was produced in the same manner as described above. However, the thickness of the charge generation layer was 0.4 μm, and the thickness of the charge transport layer was 16 μm.
And

The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation was 3.2 (μ
J / cm ² ).

Table 34 shows the results.

Example 167 The weight average molecular weight of the N-methoxymethylated 6 nylon resin was 150,000, the weight average molecular weight of the alcohol-soluble copolymer resin was 100,000, and the weight average molecular weight of the polyvinyl butyral resin was 80,000. Use 0.
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 163, except that 4 g and the charge transport material were Compound Example 5- (61). However, the thickness of the undercoat layer is 0.8 μm,
The thickness of the charge generation layer is 0.3 μm, and the thickness of the charge transport layer is 1
The thickness was 6 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 166.

Table 34 shows the results.

Example 168 N-methoxymethylated 6 nylon resin had a weight average molecular weight of 100,000, its use amount of 3 g, and a dispersion time of 10
An electrophotographic photoreceptor was prepared in the same manner as in Example 164 except that the time and the charge transporting substance were changed to Compound Example 6- (121). However, the thickness of the charge transport layer was 18 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 166.

[0555] The results are shown in Table 34.

Example 169 An electrophotographic photosensitive member was prepared in the same manner as in Example 164, except that the amount of the polyvinyl butyral resin used was 0.5 g and the charge transporting substance was Compound Example 7- (20). However,
The thickness of the undercoat layer is 0.8 μm, and the thickness of the charge generation layer is 0.1 μm.
3 μm, and the thickness of the charge transport layer was 16 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation was 3.9 (μJ
/ Cm ² ) and the number of copies is 2,000.

The results are shown in Table 34.

Example 170 The weight average molecular weight of N-methoxymethylated 6 nylon resin was 150,000, the weight average molecular weight of alcohol-soluble copolymerized nylon resin was 50,000, and the charge-generating substance was 2
g, the weight average molecular weight of the polyvinyl butyral resin is 15
Example 1 was the same as Example 1 except that the charge transport material was changed to Compound Example 8- (18), and the weight average molecular weight of the polymethyl methacrylate resin was set to 50,000.
In the same manner as in Example No. 64, an electrophotographic photosensitive member was produced. However, the thickness of the charge transport layer was 16 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation was 3.0 (μ
J / cm ² ).

Table 34 shows the results.

Example 171 N-methoxymethylated 6 nylon resin having a weight average molecular weight of 150,000 and a charge transporting substance of Compound 9-
An electrophotographic photosensitive member was prepared in the same manner as in Example 164 except that (11) was used. However, the thickness of the undercoat layer is 0.5 μm.
m, the thickness of the charge generation layer was 0.3 μm, and the thickness of the charge transport layer was 16 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 170.

[0564] The results are shown in Table 34.

Example 172 Example 164 was repeated except that the amount of polyvinyl butyral was 0.4 g, the charge transporting substance was Compound Example 10- (89), and the amount of the polymethyl methacrylate resin was 13 g.
An electrophotographic photoreceptor was produced in the same manner as described above. However, the thickness of the charge generation layer was 0.3 μm, and the thickness of the charge transport layer was 16 μm.
And

[0566] The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation is 2.5 (μ
J / cm ² ).

The results are shown in Table 34.

Example 173 The weight average molecular weight of N-methoxymethylated 6 nylon resin was 100,000, the weight average molecular weight of alcohol-soluble copolymerized nylon was 50,000, the amount used was 7 g, and the amount of polyvinyl butyral resin was 0.4 g, the charge transport material was Compound Example 11- (18), and the amount used was 13;
An electrophotographic photoreceptor was prepared in the same manner as in Example 164 except that g was used. However, the thickness of the charge transport layer was 17 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation is 2.6 (μ
J / cm ² ).

[0570] The results are shown in Table 34.

[0571]

[0572]

[0573]

Example 175 The weight average molecular weight of the N-methoxymethylated 6 nylon resin was 100,000, the weight average molecular weight of the alcohol-soluble copolymerized nylon resin was 50,000, and the weight average molecular weight of the polyvinyl butyral resin was 150,000. The dispersion time was 10 hours, and the charge transporting substance was Compound Example 13- (26),
The weight average molecular weight of the polymethyl methacrylate resin is 5
Evaluation was carried out in the same manner as in Example 164, except that the amount of 000 and the amount used were 15 g. However, the thickness of the charge generation layer was 0.3 μm, and the thickness of the charge transport layer was 18 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation was 4.5 (μ
J / cm ² ).

[0576] The results are shown in Table 34.

Example 176 An electrophotographic photosensitive member was produced in the same manner as in Example 164, except that the charge transporting substance was Compound Example 14- (19) and the amount of the polymethyl methacrylate resin used was 12 g. However, the thickness of the charge transport layer was 14 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 164. However, the exposure amount at the time of image evaluation is 2.5 (μ
J / cm ² ), and the number of copies was 3,000.

The results are shown in Table 34.

Example 177 The weight average molecular weight of the N-methoxymethylated 6 nylon resin was 100,000, the weight average molecular weight of the polyvinyl butyral resin was 50,000, the amount used was 0.6 g, the amount of dioxane was 60 g, the charge transport material. To Compound Example 15- (1
An electrophotographic photosensitive member was prepared in the same manner as in Example 164, except that 4) and the weight average molecular weight of the polymethyl methacrylate resin was changed to 60,000. However, the thickness of the charge generation layer was 0.1 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 164.

[0583] The results are shown in Table 34.

[0583]

[0584]

[0585]

[0586]

[Table 49]

[0587]

[Table 50]

Example 179 JP-A-62-67094 (USP: 4,664,641)
997), and 5 g of oxytitanium phthalocyanine obtained according to the production example disclosed in
00 g of polyvinyl benzal resin (benzalization degree 7
(5 mol%, weight average molecular weight 150,000) was dissolved in the solution, and dispersed in a ball mill for 10 hours. After this dispersion was diluted, it was applied on an aluminum sheet with a Meyer bar and dried at 80 ° C. for 30 minutes to form a 0.1 μm charge generation layer.

Next, Compound Example 1 was used as a charge transporting substance.
(40) A solution prepared by dissolving 4 g of bisphenol Z-type polycarbonate resin (weight average molecular weight: 35,000) in 40 g of monochlorobenzene was applied by a Meyer bar onto the previously formed charge generating layer with a Meyer bar, and the solution was heated at 120 ° C. for 1 hour. It was dried to form a 12 μm charge transport layer. The photoconductor thus manufactured was evaluated in the same manner as in Example 163.

[0590] The results are shown in Table 35.

Example 180 7 g of the oxytitanium phthalocyanine used in Example 179 was added to 100 g of cyclohexanone to a polyvinyl benzal resin (benzal degree: 78 mol%, weight average molecular weight: 1).
(000,000) was dissolved in a solution of 4 g and dispersed in a ball mill for 48 hours. After this dispersion was diluted, it was applied on an aluminum sheet with a Meyer bar and dried at 90 ° C. for 30 minutes to form a 0.20 μm charge generation layer.

Next, Compound Example 2- was used as a charge transport material.
A solution prepared by dissolving 5 g of the compound of (73) and 5 g of bisphenol Z-type polycarbonate resin (weight average molecular weight: 100,000) in 80 g of chlorobenzene was applied on the previously formed charge generating layer with a Meyer bar, and then heated at 140 ° C. After drying for 1 hour, a 20 μm charge transport layer was formed.

The obtained photoreceptor was evaluated in the same manner as in Example 164.

The results are shown in Table 35.

Example 181 The weight average molecular weight of a polyvinyl benzal resin was 120,
An electrophotographic photoreceptor was produced in the same manner as in Example 180, except that the dispersion time was 2,000, the drying time of the charge generation layer was 1 hour, and the charge transporting material was Compound Example 3- (76). However, the thickness of the charge generation layer was 0.4 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 165.

Table 35 shows the results.

Example 182 The dispersion time was 20 hours and the charge transporting material was Compound Example 4-
An electrophotographic photosensitive member was prepared in the same manner as in Example 180 except that (29) was used. However, the thickness of the charge generation layer is 0.3
μm.

The obtained photoreceptor was evaluated in the same manner as in Example 166.

The results are shown in Table 35.

Example 183 The dispersion time was 20 hours, and the charge transport material was changed to Compound Example 5- (7).
An electrophotographic photosensitive member was produced in the same manner as in Example 180, except that 3) and the amount of the polycarbonate resin used was changed to 3.5 g.

The obtained photosensitive member was evaluated in the same manner as in Example 167.

The results are shown in Table 35.

Example 184 The weight average molecular weight of a polyvinyl benzal resin was 800,
An electrophotographic photoreceptor was prepared in the same manner as in Example 180 except that the dispersion time was 2,000, the dispersion time was 20 hours, and the charge transport material was Compound Example 6- (108).

The obtained photoreceptor was evaluated in the same manner as in Example 168.

Table 35 shows the results.

Example 185 The amount of oxytitanium phthalocyanine used was 8 g, and the weight average molecular weight of the polyvinyl benzal resin was 50,000.
0, dispersion time: 20 hours, charge transport material: Compound Example 7-
(62) Example 18 except that the amount of the polycarbonate resin used was 7 g and the drying time of the charge transport layer was 30 minutes.
An electrophotographic photosensitive member was prepared in the same manner as in Example 1.

The obtained photoreceptor was evaluated in the same manner as in Example 169.

Table 35 shows the results.

(Example 186) The charge transport material was changed to Compound Example 8- (77) and the amount of the polycarbonate resin used was changed to 6.
An electrophotographic photosensitive member was produced in the same manner as in Example 180 except that the amount was changed to g. However, the thickness of the charge transport layer was 19 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 170.

[0611] The results are shown in Table 35.

Example 187 An electrophotographic photosensitive member was prepared in the same manner as in Example 180, except that the charge transporting substance was Compound Example 9- (47) and the amount of the polycarbonate resin was changed to 7 g. However, the thickness of the charge transport layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 171.

[0615] The results are shown in Table 35.

Example 188 The dispersion time was 40 hours, and the charge transport material was Compound Example 10-
(68), the weight average molecular weight of the polycarbonate resin is 8
An electrophotographic photoreceptor was prepared in the same manner as in Example 180 except that the amount of 000 and the amount used were 6 g. However,
The thickness of the charge generation layer is 0.4 μm, and the thickness of the charge transport layer is 1
8 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 172.

[0618] The results are shown in Table 35.

Example 189 The procedure of Example 180 was repeated, except that the amount of the polyvinyl benzal resin used was 7 g, the dispersion time was 20 hours, the charge transport material was Compound Example 11- (20), and the amount of the polycarbonate used was 7 g. Thus, an electrophotographic photosensitive member was manufactured. However,
The thickness of the charge generation layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 173.

[0621] The results are shown in Table 35.

[0622]

[0623]

[0624]

Example 191 The amount of oxytitanium phthalocyanine used was 8 g, and the weight average molecular weight of the polyvinyl benzal resin was 80,00.
0, the drying temperature of the charge generation layer was 120 ° C., the charge transport material was Compound Example 13- (62), and the same amount as in Example 180 was used except that the amount of the polycarbonate resin used was 7 g and the drying time of the charge transport layer was 30 minutes. Thus, an electrophotographic photosensitive member was manufactured.

The obtained photoreceptor was evaluated in the same manner as in Example 175.

[0627] The results are shown in Table 35.

Example 192 Weight average molecular weight of polyvinyl benzal resin: 500,0
An electrophotographic photoreceptor was prepared in the same manner as in Example 180, except that the dispersion time was 24 hours, and the charge transport material was Compound Example 14- (73).

The obtained photoreceptor was evaluated in the same manner as in Example 176.

[0631] The results are shown in Table 35.

Example 193 The charge transport substance was Compound Example 15- (83), the weight average molecular weight of the polycarbonate resin was 50,000, and the solvent for the charge transport layer was chlorobenzene / N, N-dimethylformamide (1 part by weight / 1 part). An electrophotographic photoreceptor was prepared in the same manner as in Example 180, except that the charge transport layer was dried at 130 ° C. and the drying time was set at 2 hours, with the exception of 70 parts by weight). However, the thickness of the charge generation layer was 0.1 μm.

[0632] Table 35 shows the results of evaluation of the obtained photosensitive members in the same manner as in Example 178.

[0633]

[0634]

[0635]

[0636]

[0637]

[0638]

[Table 51]

[0639]

[Table 52]

Example 195 The following formula

[0641]

[Outside 409] 2g of a dye represented by the following formula:
(30) 4 g was mixed with 30 g of a toluene (70 parts by weight) -dioxane (30 parts by weight) solution of a polycarbonate resin (weight average molecular weight of 30,000), and the mixture was mixed with a ball mill to give 15 parts.
Time dispersed. This dispersion was dried at 110 ° C. for 1 hour to form a 15 μm photosensitive layer.

The photosensitive member thus obtained was evaluated in the same manner as in Example 1.

[0643] The results are shown in Table 36.

[0644]

[Table 53]

Example 196 A 5% methanol solution of alcohol-soluble copolymerized nylon (weight average molecular weight: 50,000) was applied on an aluminum substrate to form an undercoat layer having a thickness of 0.5 μm after drying.

Next, the following formula

[0647]

[Outside 410] Was dispersed in 50 ml of tetrahydrofuran with a sand mill.

Next, Compound Example 2- as a charge transporting substance
5 g of the compound of (67), 7 g of a polycarbonate resin (weight average molecular weight 50,000) and 50 g of a chlorobenzene (70 parts by weight) -dichloromethane (30 parts by weight) solution were added to the dispersion prepared above, and the mixture was further added with a sand mill for 25 minutes.
Time dispersed.

This dispersion was applied on a previously formed undercoat layer using a Meyer bar so that the film thickness after drying was 18 μm, and dried.

The charging characteristics of the electrophotographic photosensitive member thus manufactured were evaluated in the same manner as in Example 11.

The results are shown in Table 37.

Example 197 An electrophotographic photosensitive member was produced in the same manner as in Example 196 except that the charge transporting material was changed to compound example 3- (73). However, the thickness of the undercoat layer was 1.0 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 196.

[0654] The results are shown in Table 37.

Example 198 An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 196 except that the charge transporting material was changed to compound example 4- (26).

The results are shown in Table 37.

Example 199 The alcohol-soluble copolymerized nylon resin had a weight average molecular weight of 80,000 and the charge transporting substance was Compound Example 5- (86).
An electrophotographic photosensitive member was prepared in the same manner as in Example 196 except that the dispersion time was changed to 24 hours. However, the thickness of the undercoat layer was 1.0 μm.

The obtained photosensitive member was evaluated in the same manner as in Example 196.

[0659] The results are shown in Table 37.

Example 200 An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 196 except that the charge transport material was changed to compound example 6- (67).

The results are shown in Table 37.

Example 201 A weight-average molecular weight of an alcohol-soluble copolymerized nylon resin was 80,000, and a charge-transporting substance was Compound Example 7- (82).
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 196 except that the dispersion time was changed to 10 hours.

The results are shown in Table 37.

Example 202 An alcohol-soluble copolymerized nylon resin having a weight average molecular weight of 100,000 and a charge transporting substance of Compound Example 8-
An electrophotographic photosensitive member was prepared in the same manner as in Example 196 except that (81) was used. However, the thickness of the undercoat layer is 1.0 μm.
m.

The obtained photoreceptor was evaluated in the same manner as in Example 196.

[0666] The results are shown in Table 37.

Example 203 An electrophotographic photosensitive member was prepared in the same manner as in Example 196 except that the charge transporting material was Compound Example 9- (55) and the dispersion time was 48 hours. However, the thickness of the undercoat layer is 0.8 μm.
m.

The obtained photoreceptor was evaluated in the same manner as in Example 196.

The results are shown in Table 37.

Example 204 An alcohol-soluble copolymerized nylon resin having a weight average molecular weight of 70,000 and an electric charge transporting compound of Compound Example 10-
An electrophotographic photosensitive member was prepared in the same manner as in Example 196 except that (55) was used. However, the thickness of the undercoat layer is 1.0 μm.
m.

The obtained photoreceptor was evaluated in the same manner as in Example 196. The results are shown in Table 37.

Example 205 Example 1 was repeated except that the charge-transporting substance was Compound Example 11- (35) and the amount of the polycarbonate resin was changed to 10 g.
An electrophotographic photosensitive member was prepared in the same manner as in No. 96, and evaluated.

The results are shown in Table 37.

[0674]

[0675]

Example 207 An electrophotographic photoreceptor was prepared in the same manner as in Example 196 except that the charge-transporting substance was compound 13- (67), the weight average molecular weight of the polycarbonate resin was 80,000, and the dispersion time was 15 hours. And evaluated.

[0677] The results are shown in Table 37.

Example 208 An electrophotographic photosensitive member was prepared in the same manner as in Example 196 except that the charge transporting material was changed to Compound Example 14- (68). However, the thickness of the undercoat layer was 1.0 μm.

The obtained photosensitive member was evaluated in the same manner as in Example 196.

[0680] The results are shown in Table 37.

Example 209 The weight average molecular weight of the alcohol-soluble copolymerized nylon resin was 80,000, and the charge transporting substance was Compound Example 15- (7
1), the weight average molecular weight of the polycarbonate resin is 35,
An electrophotographic photoreceptor was prepared in the same manner as in Example 196, except that the amount used was 10 g and the dispersion time was 20 hours. However, the thickness of the undercoat layer was 1 μm, and the thickness of the photosensitive layer was 19 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 196.

[0684] The results are shown in Table 37.

[0684]

[Table 54]

Example 210 10 g of Compound Example 1- (37) as a charge transporting material and 10 of a polycarbonate resin (weight average molecular weight 30,000) 10
g was dissolved in 120 g of monochlorobenzene, and this solution was applied on an aluminum sheet with a Meyer bar to obtain a dry film having a thickness of 12 μm.
m of the charge transport layer was formed.

Next, 2 g of the pigment used in Example 196 was
A coating solution was prepared by dispersing 1 g of butyral resin (butyralization degree: 75 mol%) in a sand mill for 15 hours together with a solution in 40 ml of cyclohexanone.

After diluting this coating solution, a charge-generating layer was provided by applying a Meyer bar onto the charge transport layer so that the film thickness after drying was 0.5 μm.

The charging characteristics of the electrophotographic photosensitive member thus manufactured were evaluated in the same manner as in Example 1. However, corona charging was performed at -5 KV.

The results are shown below. V ₀ : -675 V
V ₁ : -660 VE _1/2 : 3.9 lux · sec
V _R: -80 V

Example 211 The compound of Example 16- (70) was used as the charge transport material, the amount of the polycarbonate resin used was 9 g, the amount of the monochlorobenzene used was 90 g, the degree of butyralization of the polyvinyl butyral resin was 70 ml%, and the amount of cyclohexanone was 45 ml and dispersed. An electrophotographic photosensitive member was produced in the same manner as in Example 210 except that the time was changed to 20 hours. However, the thickness of the charge transport layer was 15 μm, and the thickness of the charge generation layer was 0.4 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

The results are shown below. V ₀ : -680 V ₁ :
_{-675VE 1/2: 3.7lux · sec V R} : -60 V

Example 212 Compound 5g of Compound Example 2- (77) as a charge-transporting substance
And polycarbonate resin (weight average molecular weight 80,00
0) 5 g was dissolved in 70 g of chlorobenzene, and this solution was applied to an aluminum sheet with a Meyer bar to obtain a dry film having a thickness of 15 g.
A μm charge transport layer was formed.

Next, the following formula

[0696]

[Outside 411] Is dispersed in a sand mill for 20 hours together with a solution prepared by dissolving 2 g of disazo pigment represented by the following formula in 50 ml of cyclohexanone in 1.5 g of polyvinyl butyral (butyralization degree: 80 mol%), diluted, and dried on the charge transport layer. It was applied with a Meyer bar so as to have a thickness of 0.5 μm to form an electrification generating layer.

The charging characteristics of the thus obtained electrophotographic photosensitive member were evaluated in the same manner as in Example 210.

[0697] The results are shown in Table 38.

Example 213 Example 2 was repeated except that the charge transport material was Compound Example 3- (6), the weight average molecular weight of the polycarbonate resin was 100,000, and the amount of the polyvinyl butyral resin used was 1 g.
In the same manner as in No. 12, an electrophotographic photosensitive member was produced. However, the thickness of the charge transport layer was 18 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

The results are shown in Table 38.

Example 214 An electrophotographic photosensitive member was prepared in the same manner as in Example 212, except that the charge-transporting substance was Compound Example 4- (33), and the dispersion time was 50 hours. However, the thickness of the charge generation layer is 0.1.
It was 3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0739] The results are shown in Table 38.

Example 215 The compound of Example 5- (95) was used as the charge-transporting substance, and the amount of use was 3
g and the weight average molecular weight of the polycarbonate resin is 5
An electrophotographic photosensitive member was produced in the same manner as in Example 212 except that the amount was changed to 000. However, the thickness of the charge transport layer is 20
μm, and the thickness of the charge generation layer was 0.6 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

The results are shown in Table 38.

Example 216 An electrophotographic photosensitive member was prepared in the same manner as in Example 212, except that the charge transporting material was changed to compound example 6- (15). However, the thickness of the charge generation layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

The results are shown in Table 38.

Example 217 An electrophotographic photoreceptor was prepared in the same manner as in Example 212, except that the charge-transporting substance was Compound Example 7- (79), the weight average molecular weight of the polycarbonate resin was 70,000, and the amount used was 6 g. Produced. However, the thickness of the charge transport layer is 20 μm.
m.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0739] The results are shown in Table 38.

Example 218 The charge-transporting substance was Compound Example 8- (50), the amount of the polycarbonate resin used was 6 g, the degree of butyralization of the polyvinyl butyral resin was 75 mol%, and the amount of use was 0.9.
An electrophotographic photoreceptor was prepared in the same manner as in Example 212 except that g was used. However, the thickness of the charge transport layer was 20 μm, and the thickness of the charge generation layer was 0.4 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0715] The results are shown in Table 38.

Example 219 An electrophotographic photosensitive member was prepared in the same manner as in Example 212, except that the charge transporting substance was Compound Example 9- (88) and the weight average molecular weight of the polycarbonate resin was 100,000. However, the thickness of the charge transport layer was 12 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0718] The results are shown in Table 38.

Example 220 Example 2 was repeated except that the charge transport material was Compound Example 10- (49), the weight average molecular weight of the polycarbonate resin was 50,000, and the amount of polyvinyl butyral was 2 g.
In the same manner as in No. 12, an electrophotographic photosensitive member was produced. However, the thickness of the charge transport layer was 17 μm, and the thickness of the charge generation layer was 0.7
μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0721] The results are shown in Table 38.

Example 221 An electrophotographic photoreceptor was prepared in the same manner as in Example 212, except that the charge transport material was Compound Example 11- (31), the weight average molecular weight of the polycarbonate resin was 50,000, and the amount used was 7 g. Fabricated and evaluated.

[0723] The results are shown in Table 38.

[0724]

[0725]

[0726]

Example 223 Electrophotography was carried out in the same manner as in Example 212 except that the charge transporting substance was Compound Example 13- (69), the weight average molecular weight of the polycarbonate resin was 100,000, and the amount of disazo pigment used was 3 g. A photoreceptor was produced. However, the thickness of the charge transport layer was 18 μm, and the thickness of the charge generation layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0739] The results are shown in Table 38.

Example 224 An electrophotographic photosensitive member was prepared in the same manner as in Example 212, except that the charge transporting material was changed to compound example 14- (75). However, the thickness of the charge transport layer was 20 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0732] The results are shown in Table 38.

Example 225 Example 212 was repeated except that the charge transport material was Compound Example 15- (90), the average molecular weight of the polycarbonate resin was 35,000, and the amount of the polyvinyl butyral resin used was 1 g.
An electrophotographic photoreceptor was produced in the same manner as described above. However, the thickness of the charge transport layer was 0.3 μm.

The obtained photoreceptor was evaluated in the same manner as in Example 210.

[0739] The results are shown in Table 38.

[0736]

[Table 55]

Example 226 A 5% methanol solution of an alcohol-soluble copolymerized nylon resin (weight average molecular weight: 80,000) was applied on an aluminum substrate to form an undercoat layer having a thickness of 1 μm after drying.

Next, 4 g of the pigment used in Example 212 was dispersed in 45 ml of tetrahydrofuran with a sand mill.

Next, Compound Example 1 was used as a charge transport material.
(30) 5 g of a polycarbonate resin (weight-average molecular weight 25,000) and 10 g of a monochlorobenzene (60 parts by weight) -dichloromethane (16,000 parts by weight) solution 50
g, added to the previously prepared dispersion, and further dispersed in a sand mill for 3 hours.

This dispersion was applied on a previously formed undercoat layer using a Meyer bar so that the film thickness after drying was 18 μm, and dried.

[0741] The charging characteristics of the photoreceptor thus manufactured were evaluated in the same manner as in Example 1.

[0739] The results are shown below.

V ₀ : +693 V V ₁ : +687 V
E _1/2 : 4.2 lux · sec V _R : + 75V

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

As described above, according to the present invention, it is possible to provide an electrophotographic photosensitive member having high sensitivity and excellent electrophotographic characteristics even when used repeatedly.

[Brief description of the drawings]

FIG. 1 is a diagram illustrating a schematic configuration example of an electrophotographic apparatus having an electrophotographic photosensitive member of the present invention.

FIG. 2 is a diagram illustrating an example of a block diagram of a facsimile having the electrophotographic photosensitive member of the present invention.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI H04N 1/29 H04N 1/29 D // C07D 333/44 C07D 333/44 (31) Priority claim number Japanese Patent Application No. 2-181627 (32) Priority date Hei 2 (1990) July 11 (33) Priority claim country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-181628 (32) Priority date Hei 2 (1990) July 11th (33) Priority claim country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-181629 (32) Priority date Hei 2 (1990) July 11 (33) Priority claim country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-181630 (32) Priority Date Hei 2 (1990) July 11 (33) Priority claim country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2 −182687 (32) Priority Date 2 (1990) July 12 (33) Priority claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-182688 (32) Priority date 2 (1990) July 12 (33) Priority claim country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-182689 (32) Priority date Hei 2 (1990) July 12 (33) Priority Claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-184185 (32) Priority date Hei 2 (1990) July 13 (33) Priority claiming country Japan (JP) (31) Priority Claim number Japanese Patent Application No. 2-184186 (32) Priority Date Hei 2 (1990) July 13 (33) Priority claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-184187 (32) Priority Japan 2 (1990) July 13 (33) Priority claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-195053 (32) Priority day Hei 2 (1990) July 25 (33) ) Priority claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-236998 (32) Priority date Hei 2 (1990) September 10 (33) Priority claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-273584 (32) Priority date Hei 2 (1990) October 11, (33) Priority claim country Japan (JP) (72) Inventor Takakazu Tanaka Shimomaruko, Ota-ku, Tokyo (30) Inside Canon Inc. (72) Noriko Otani 3-30-2 Shimomaruko, Ota-ku, Tokyo Inventor Canon (72) Inventor Susumu Nagahara 3-30-2 Shimomaruko, Ota-ku, Tokyo No. Canon Inc. (72) Inventor Hisami Tanaka 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (56) References JP-A-1-152461 (JP, A) JP-A-2- 156247 (JP, A) JP-A-1-40835 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G03G 5/00-5/16

Claims (8)

(57) [Claims] 1. An electrophotographic photoreceptor having a photosensitive layer on a conductive support, wherein the photosensitive layer comprises a charge-generating substance and the following formula (1). (A represents an aromatic ring group derived from an aromatic compound having a reduction potential of −1.05 V or more, and R ¹ , R ² , R ³ ,
R ⁴ and R ⁵ represent a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aromatic ring group which may have a substituent, and R ¹ and R ² , R ³ , R ⁴ and R ⁵ may be the same or different. Where R ⁴ and R ⁵
Except that both are hydrogen atoms. n represents an integer of 0 or 1, and m represents an integer of 1 or 2. An electrophotographic photoreceptor comprising a charge transporting substance having an electron transporting ability represented by the formula (1). 2. The electrophotographic photoreceptor according to claim 1, wherein said photosensitive layer has a charge generating layer containing a charge generating substance and a charge transporting layer containing a charge transporting substance. 3. The electrophotographic photoconductor according to claim 2, wherein the electrophotographic photoconductor has a conductive support, a charge generation layer and a charge transport layer in this order. 4. An electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the photosensitive layer comprises a charge generating substance and the following formulas (2) to (11), (13), (14) and (1).
5) An electrophotographic photoreceptor comprising a charge transporting material having an electron transporting ability represented by a formula selected from the group consisting of: Equation (2) (Wherein, R _2-1 , R _2-2 , R _2-3 and R _2-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, Or [outside 4] And at least two or more of R _{2-1 to} R _2-4 are Or [outside 6] R _2-5 and R _2-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _2-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, and
2, r is an integer of 0 or 1, and R _2-6 and R _2-7 are directly linked to each other or linked via a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. May be formed. ) Equation (3) (Wherein, R _3-1 , R _3-2 , R _3-3 and R _3-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, Or [outside 9] And at least two or more of R _{3-1 to} R _3-4 are Or [outside 11] R _3-5 and R _3-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group; R _3-7 represents an alkyl group, an aralkyl group which may have a substituent, An aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, 2, and r are any integers of 0 and 1; _3-6 and R _3-7 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. ) Equation (4) (Wherein, R _4-1 represents a thiophene ring group having a nitro group;
_4-2 and R _{4-3 each} represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, nitro Group, cyano group, Or [outside 14] And at least one of R _4-2 and R _4-3 is Or [outside 16] Wherein R _4-4 and R _{4-5 each} represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_4-6 is an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent. Wherein f and g are 1, 2, h is an integer of 0 or 1, and R _4-5 and R _4-6 are each directly or a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom, a sulfur They may be bonded via an atom to form a ring. ) Equation (5) (Wherein, R _5-1 , R _5-2 , R _5-3 , R _5-4 , R _5-5 and R
_5-6 are a hydrogen atom, a halogen atom, an alkyl group optionally having a substituent, an aralkyl group optionally having a substituent, an aromatic ring group optionally having a substituent, Or [outside 19] And at least two or more of R _{5-1 to} R _5-6 are Or [outside 21] Wherein R _5-7 and R _5-8 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_5-9 is an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent. And p and q are 0, 1, 2, and r are any integers of 0 and 1,
_5-8 and R _5-9 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom or sulfur atom to form a ring. ) Equation (6) (Wherein, R _6-1 , R _6-2 , R _6-3 , R _6-4 , R _6-5 and R
_6-6 are a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, Or [outside 24] And at least two or more of R _{6-1 to} R _6-6 are Or [outside 26] R _6-7 and R _6-8 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _6-9 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, and
2, r is an integer of 0 or 1, and R _6-8 and R _6-9 are linked directly to each other or via a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. May be formed. ) Equation (7) (Wherein, R _7-1 , R _7-2 , R _7-3 and R _7-4 represent a hydrogen atom,
Halogen atom, alkyl group, aralkyl group, aromatic ring group,
-(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R _7-5
Or [outside 28] And at least two or more of R _{7-1 to} R _{7-4 are-}
(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R _7-5 or Wherein R _5-5 and R _7-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_7-7 represents an alkyl group, an aralkyl group, an aromatic ring group or a heterocyclic group, p and q are each an integer of 0, 1, 2, r is 0 or 1, and R _7-5 and R _{7 -7} may be linked to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom or sulfur atom to form a ring. ) Equation (8) (Wherein, R _8-1 , R _8-2 , R _8-3 and R _8-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _p -NO ₂ ,-( CH = C
H) _{q- R8-5} or Wherein at least two of R _{8-1 to} R _{8-4 are-} (CH = CH) _p -NO ₂ ,-(CH = CH) _q -R
_8-5 or [outside 32] Wherein R _8-5 and R _8-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group;
_8-7 is an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent. And p and q are 0, 1, 2, and r are any integers of 0 and 1,
_8-6 and R _8-7 may be linked to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom or sulfur atom to form a ring. ) Equation (9) (Wherein, R _9-1 , R _9-2 , R _9-3 and R _9-4 represent a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _f -NO ₂ ,-( CH = C
H) _g- R _9-5 or Wherein at least two or more of R _{9-1 to} R _{9-4 are-} (CH = CH) _f -NO ₂ ,-(CH = CH) _h -R
_9-5 or [Outside 35] R _9-5 and R _{9-6 each} represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group; R _9-7 represents an alkyl group which may have a substituent; An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein i, f and g are 1, 2, and h are 0, 1 It is any integer, and R _9-6 and R _9-7 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. ) Equation (10) (Wherein, R _10-1 , R _10-2 , R _10-3 and R _10-4 are a hydrogen atom, a halogen atom, an alkyl group which may have a substituent,
An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _f -NO ₂ ,-(CH =
CH) _g -R _10-5 or Wherein at least two or more of R _{10-1 to} R _{10-4 are-} (CH = CH) _f -NO ₂ ,-(CH = CH) _g-
R _10-5 or [outside 38] R _10-5 and R _{10-6 each} represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group; R _10-7 represents an alkyl group having a substituent; an aralkyl group having a substituent; A substituent-containing aromatic ring group or a substituent-containing heterocyclic group; i, f, and g are 1, 2, and h are 0 or 1; Further, R _10-6 and R _10-7 may be bonded to each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. ) Equation (11) (Wherein, R _11-1 and R _11-2 may have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, and a substituent. Aromatic ring group,
-(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R
_11-5 or [outside 40] Wherein at least one of R _11-1 and R _{11-2 is-} (CH = CH) _p -NO ₂ ,-(CH = CH)
_q -R _11-5 or [outside 41] R _11-5 and R _11-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _11-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, R _11-6 and R _11
11-7 may be formed by bonding rings directly to each other or through a saturated hydrocarbon, unsaturated hydrocarbon, oxygen atom, sulfur atom, etc., and R _11-3 and R _11-4 are a halogen atom, An alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic ring group which may have a substituent, a heterocyclic group which may have a substituent, a nitro group or a cyano group And p and q are 0, 1, 2, and r is any integer of 0 or 1. ) Equation (13) (Wherein, R _13-1 , R _13-2 , R _13-3 and R _13-4 represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent,
An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _p -NO ₂ ,-(CH =
CH) _q -R _13-5 or And at least two or more of R _{13-1 to} R _{13-4 are-}
(CH = CH) _p -NO ₂ ,-(CH = CH) _q -R _13-5
Or [outside 44] R _13-5 and R _13-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _13-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein p and q are 0, 1, and
2, r is an integer of 0 or 1, and R _13-6 and R _13-7 are bonded to each other directly or through a saturated hydrocarbon, an unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. May be formed. ) Equation (14) (Wherein, R _14-1 , R _14-2 , R _14-3 and R _14-4 are a hydrogen atom, a halogen atom, an alkyl group which may have a substituent,
An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent,-(CH = CH) _f -NO ₂ ,-(CH =
CH) _g -R _14-5 or And at least two or more of R _{14-1 to} R _{14-4 are-
(CH = CH) f -NO 2} , - (CH = CH) g -R 14-5
Or [outside 47] R _14-5 and R _14-6 represent an aromatic ring group having a nitro group or a heterocyclic group having a nitro group, and R _14-7 represents an alkyl group which may have a substituent, An aralkyl group which may have a substituent, an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent, wherein k, f and g are 1, 2, h are 0, 1 It is any integer, and R _14-6 and R _14-7 may combine with each other directly or via a saturated hydrocarbon, unsaturated hydrocarbon, an oxygen atom or a sulfur atom to form a ring. ) The following formula (15) (Wherein, R _15-1 , R _15-2 and R _15-3 represent-(CH ＝ C
_{H) s -NO 2, - (} CH = CH) t -R 15-4 or ## outside 49] And s is 0, 1, t, u is any integer of 0 or 1, and R _15-4 and R _15-5 are an aromatic ring group having a nitro group or a heterocyclic group having a nitro group. And R _15-6 represents an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent or a group which has a substituent. X represents a good heterocyclic group, and X represents a divalent aromatic hydrocarbon ring group which may have a substituent or a residue necessary for forming a saturated hydrocarbon ring together with adjacent carbon atoms. ) 5. The electrophotographic photoreceptor according to claim 4, wherein said photosensitive layer has a charge generating layer containing a charge generating substance and a charge transporting layer containing a charge transporting substance. 6. The electrophotographic photoconductor according to claim 5, wherein the electrophotographic photoconductor has a conductive support, a charge generation layer, and a charge transport layer in this order. 7. An electrophotographic photoreceptor according to claim 1, wherein said electrostatic latent image is formed on said electrophotographic photosensitive member, said electrostatic latent image is formed on said electrophotographic photosensitive member, and said developed image is transferred onto a transfer material. An electrophotographic apparatus, comprising: 8. The electrophotographic photoreceptor according to claim 4, wherein the electrostatic latent image forming means, the means for developing the formed electrostatic latent image, and the means for transferring the developed image to a transfer material are provided. An electrophotographic apparatus, comprising: