JPH10114728A - Stilbene derivative and electrophotographically sensitive material using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound having an asymmetric structure of a diphenylamino group at a molecular terminal, excellent in compatibility with a binder resin, high charge-transferring degree and capable of giving a highly sensitive electrophotographically sensitive material. SOLUTION: This compound is composed of at least one kind of a stilbene derivative expressed by formula I (R<1> and R<3> are each an alkyl; R<2> and R<4> are each H or an alkyl) and formula II (R<5> R<14> are each H or an alkyl, at least three of the R<5> to R<9> are each an alkyl and at least three of the R<10> to R<14> are each alkyl). In the stibene derivative of the formula I, a stilbene derivative in which R<1> is same as R<3> and R<2> is same R<4> is obtained by synthesizing a triphenylamine derivative from a reaction of an aniline derivative of formula III with iodobenzene, formulating by reacting in the presence of phosphorus oxychloride, then reacting the formate of the triphenylamine with a bisphoshate derivative. The stilbene derivative can be used as a photosensitive layer on an electroconductive base material of a electrophotographically sensitive material.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a stilbene derivative having an excellent charge transporting ability, and an electrophotography containing the stilbene derivative for use in an image forming apparatus such as an electrostatic copying machine, a facsimile, a laser beam printer and the like. And a photoreceptor.

[0002]

2. Description of the Related Art In the above-mentioned image forming apparatus, various organic photosensitive members having sensitivity in a wavelength region of a light source used in the image forming apparatus are used. This organic photoreceptor is easier to manufacture than conventional inorganic photoreceptors, has a wide variety of photoreceptor materials such as charge transport agents, charge generators, and binder resins, and has a high degree of freedom in functional design. Due to its advantages, it has been widely used in recent years.

[0003] The organic photoreceptor includes a single-layer type photoreceptor in which a charge transporting agent and a charge generating agent are dispersed in the same photosensitive layer.
There is a laminated photoreceptor in which a charge generating layer containing a charge generating agent and a charge transporting layer containing a charge transporting agent are laminated.

[0004]

As the charge transporting agent used in the above-mentioned organic photoreceptor, JP-A-7-244389 discloses a compound represented by formula (3):

[0005]

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(Wherein, R ^A , R ^B , R ^C and R ^D represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent or an alkoxy group. And R ^E and R ^F represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an aryl group.). JP-A-50-31773 also discloses a stilbene derivative similar to the above-mentioned publication.

However, all of the stilbene derivatives specifically exemplified in the above-mentioned publications have a problem that the compatibility with the binder resin is insufficient and the photosensitivity has not reached a practical level. Therefore, an object of the present invention is to solve the above-mentioned problems, to provide a high charge-sensitivity electrophotographic photosensitive member having high compatibility with a binder resin, and an electrophotographic photosensitive member using the same. To provide.

[0008]

Means for Solving the Problems The inventors of the present invention have conducted various studies to solve the above problems,
Among the stilbene derivatives represented by (3), compounds in which the diphenylamino group at the molecular end is asymmetric, particularly (i)
A compound in which one of the phenyl groups in the diphenylamino group has no substituent, and the other phenyl group has an alkyl group at only two positions at the para and meta positions or at only one position at the para position, or (ii) the diphenylamino group Has no substituent on one phenyl group and 3 on the other phenyl group.
The compound having from 5 to 5 alkyl groups has a new fact that it has better compatibility with the binder resin and higher charge mobility than the stilbene derivatives specifically exemplified in the above-mentioned publication, and has completed the present invention. I came to.

That is, the stilbene derivative of the present invention is
General formula (1):

[0010]

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(Where R¹And R^ThreeAre the same or different
Represents an alkyl group;^TwoAnd R ^FourAre the same or different
Represents a hydrogen atom or an alkyl group. )
It is characterized by that. Also, other stilbene invitations of the present invention are provided.
The conductor has the general formula (2):

[0012]

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(Wherein R^Five, R⁶, R⁷, R⁸, R⁹,
R^Ten, R¹¹, R¹², R¹³And R¹⁴Are the same or different
Represents a hydrogen atom or an alkyl group. Where R^Five, R
⁶, R ⁷, R⁸And R⁹At least three of them
A kill group;^Ten, R¹¹, R ¹², R¹³And R¹⁴Horse
At least three represent an alkyl group. )
And features.

The stilbene derivatives of the present invention represented by the above general formulas (1) and (2) are compounds not specifically described in the above-mentioned gazettes, and also include compounds not specifically disclosed in the above-mentioned gazettes. Also has high compatibility with the binder resin,
In addition, since the charge mobility is high, a highly sensitive electrophotographic photosensitive member can be provided. Further, the electrophotographic photoreceptor of the present invention comprises:
An electrophotographic photosensitive member having a photosensitive layer provided on a conductive substrate, wherein the photosensitive layer contains at least one stilbene derivative represented by the above general formulas (1) and (2). I do.

The electrophotographic photoreceptor of the present invention has the general formula
Since the photosensitive layer contains at least one of the stilbene derivatives represented by (1) and (2), the speed of transporting the charges (holes) generated by the charge generating agent is high, that is, the charge mobility is low. Large and excellent in light sensitivity during charging and exposure. As a result, according to the electrophotographic photoreceptor of the present invention, higher sensitivity can be obtained than when the stilbene derivative (3) specifically exemplified in the above publication is used as a hole transporting agent.

Further, the photosensitive layer contains a charge generating agent and an electron transporting agent in addition to at least one of the stilbene derivatives represented by the above general formulas (1) and (2). When it is a layer, an electrophotographic photoreceptor with higher sensitivity can be obtained.

[0017]

DESCRIPTION OF THE PREFERRED EMBODIMENTS First, a stilbene derivative of the present invention
(1) and (2) will be described in detail. The above general formulas (1) and (2)
Where R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ ,
Examples of the alkyl group corresponding to R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁴ include, for example, methyl, ethyl, n-
Propyl, isopropyl, n-butyl, isobutyl, s
And groups having 1 to 4 carbon atoms, such as -butyl and t-butyl.

The stilbene derivative (1) of the present invention includes the following general formulas (11) to (13). In particular, stilbene derivatives represented by general formulas (11) and (12) are preferably used. .

[0019]

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(In the formula, R ^{1 to} R ⁴ are the same as described above.) As specific examples of the stilbene derivative represented by the general formula (1), substituents corresponding to the groups R ^{1 to} R ⁴ are as follows. Tables 1-2
Shown in In Tables 1 and 2, compounds having a compound number starting with "11-" are stilbene derivatives contained in the general formula (11), and compounds having a compound number starting with "12-" are represented by the general formula (1
It is a stilbene derivative included in 2). Tables 1 and 2
In the formula, H is a hydrogen atom, Me is a methyl group, Et is an ethyl group,
n-Pr indicates an n-propyl group, i-Pr indicates an isopropyl group, n-Bu indicates an n-butyl group, and s-Bu indicates an s-butyl group.

[0021]

[Table 1]

[0022]

[Table 2]

On the other hand, the stilbene derivative (2) of the present invention includes the following general formulas (21) to (23).
Stilbene derivatives represented by (21) and (22) are preferably used.

[0024]

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(In the formula, R ^{5 to} R ¹⁴ are the same as described above.) As specific examples of the stilbene derivative represented by the general formula (2), substituents corresponding to the groups R ^{5 to} R ¹⁴ are shown below. Tables 3-4
Shown in In Tables 3 and 4, the compound numbers are "21-" and "22".
Those beginning with “-” are stilbene derivatives included in general formulas (21) and (22), respectively. H, Me and Et in Tables 3 and 4 are the same as described above. t-Bu represents a t-butyl group.

[0026]

[Table 3]

[0027]

[Table 4]

The method of synthesizing the stilbene derivative (1) of the present invention will be described by taking as an example the case where R ¹ and R ³ are the same group and R ² and R ⁴ are the same group. In this case, first
As shown in the following reaction formula (I), the starting materials aniline derivative (90) and iodobenzene (91) were mixed at a ratio of 1: 2 (molar ratio).
In a solvent such as nitrobenzene, and refluxed with a catalyst such as anhydrous potassium carbonate or copper to synthesize a triphenylamine derivative (92) .Then, the triphenylamine derivative (92) was converted into dimethylformamide, N-methyl. It is added to a solvent such as formanilide and reacted in the presence of phosphorus oxychloride to formylate.

Reaction formula (I):

[0030]

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(In the formula, R ¹ and R ² are the same as described above.) Then, as shown in the following reaction formula (II), bisphosphate ester derivative (94) dissolved in a solvent such as tetrahydrofuran
To the formyl form of triphenylamine (93)
By dropping at a ratio of 2 (molar ratio) and reacting,
The stilbene derivative (1 ′) is obtained.

Reaction formula (II):

[0033]

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(In the formula, R ¹ and R ² are the same as described above.) In the synthesis of the stilbene derivative (1), when the groups R ¹ and R ³ or R ² and R ⁴ are different groups, For example, as shown in the following reaction formula (III), first, a monophosphoric acid ester (96) is synthesized by reacting methyl benzyl chloride (95) with a phosphite triester. Reaction of 93) yields the monostilbene derivative (97), which is further chlorinated to give compound (98).

Reaction formula (III):

[0036]

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(In the formula, R ¹ and R ² are the same as described above.) Then, as shown in the following reaction formula (IV), the compound (98)
Is reacted with phosphite triester to obtain a compound (99),
The stilbene derivative (1) is obtained by reacting this with the formyl derivative (93 ′) of triphenylamine. Reaction formula (IV):

[0038]

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(In the formula, R ^{1 to} R ⁴ are the same as described above.) On the other hand, the stilbene derivative represented by the general formula (2) is the same as that of the above-mentioned triphenylamine formyl derivatives (93) and (94). The compound can be synthesized in the same manner as in the above-mentioned reaction formulas (I) and (II) or reaction formulas (III) and (IV) except that the substituent is different. The stilbene derivatives represented by the above general formulas (1) and (2) have a large charge mobility as described above, that is, have a high hole transporting ability, and thus are suitable as a hole transporting agent in an electrophotographic photoreceptor. In addition to the above, it can be used in various fields such as a solar cell and an electroluminescent element.

Next, the electrophotographic photosensitive member of the present invention will be described in detail. The electrophotographic photoreceptor of the present invention has the general formula
(1) and one of the stilbene derivatives represented by the general formula (2)
A photosensitive layer containing one or more species is provided on a conductive substrate. As described above, there are a single-layer type and a stacked-type photoreceptor, and the present invention can be applied to any of them.

The single layer type photoreceptor has a single photosensitive layer provided on a conductive substrate. This photosensitive layer contains at least one stilbene derivative (hole transporting agent) represented by the general formulas (1) and (2), a charge generating agent, a binder resin, and, if necessary, an electron transporting agent. It is formed by dissolving or dispersing in an appropriate solvent, applying the obtained coating liquid on a conductive substrate, and drying. Such a single-layer type photoreceptor can be applied to both positive and negative charging types in a single configuration, and has a simple layer configuration and excellent productivity.

The single-layer type electrophotographic photoreceptor of the present invention is disclosed in JP-A-7-244389 and JP-A-50-31.
As compared with a single-layer type electrophotographic photoreceptor obtained by using a stilbene derivative specifically exemplified in JP 773 as a hole transporting agent, the residual potential of the photoreceptor is greatly reduced, and the sensitivity is improved. doing. Further, when the electron transporting agent is further contained in the photosensitive layer of the single-layer electrophotographic photoreceptor of the present invention, the transfer of electrons between the charge generating agent and the hole transporting agent is efficiently performed, The sensitivity of the photoreceptor is further improved.

On the other hand, in the laminate type photoreceptor, first, a charge generating layer containing a charge generating agent is formed on a conductive substrate by means such as vapor deposition or coating, and then the general formula ( It is produced by applying a coating solution containing at least one stilbene derivative (hole transporting agent) represented by 1) and the general formula (2) and a binder resin, followed by drying to form a charge transporting layer. You. Conversely, a charge transport layer may be formed on a conductive substrate, and a charge generation layer may be formed thereon. However, since the charge generation layer is very thin compared to the charge transport layer, it is preferable to form the charge generation layer on a conductive substrate and to form the charge transport layer thereon for protection. .

The positive / negative charging type is selected depending on the order of forming the charge generating layer and the charge transporting layer and the type of the charge transporting agent used in the charge transporting layer. For example, as described above, when a charge generation layer is formed on a conductive substrate and a charge transport layer is formed thereon, as the charge transport agent in the charge transport layer, the stilbene derivative (1) of the present invention, (( When a hole transporting agent such as 2) is used, the photoreceptor becomes negatively charged. In this case, the charge generation layer may contain an electron transport agent.

The laminated electrophotographic photoreceptor of the present invention is disclosed in JP-A-7-244389 and JP-A-50-31.
The residual potential of the photoreceptor is greatly reduced and the sensitivity is improved as compared with the laminated electrophotographic photoreceptor using the stilbene derivative described in JP-A-773-703 as a hole transport agent.
As described above, the electrophotographic photoreceptor of the present invention can be applied to any of a single-layer type and a laminated type, but can be used for both positive and negative charging types, and has a simple structure and is easy to manufacture. The single-layer type is preferred from the viewpoints that film defects at the time of forming the layer can be suppressed, the interface between the layers is small, and the optical characteristics can be improved.

Next, various materials used for the electrophotographic photosensitive member of the present invention will be described. << Charge Generating Agent >> Examples of the charge generating agent used in the present invention include compounds represented by the following general formulas (CG1) to (CG12). (CG1) Metal-free phthalocyanine

[0047]

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(CG2) Oxotitanyl phthalocyanine

[0049]

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(CG3) Perylene pigment

[0051]

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(In the formula, R ^g1 and R ^g2 are the same or different and each represents a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group, alkanoyl group or aralkyl group having 18 or less carbon atoms.) (CG4) ) Bisazo pigment

[0053]

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[Wherein Cp ¹ and Cp ² are the same or different and represent a coupler residue, and Q represents the following formula:

[0055]

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(Wherein R ^g3 represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, and the alkyl group, the aryl group or the heterocyclic group may have a substituent.
Represents 0 or 1. )

[0057]

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(In the formula, R ^g4 and R ^g5 are the same or different and represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, an alkoxy group, an aryl group or an aralkyl group.)

[0059]

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(In the formula, R ^g6 represents a hydrogen atom, an ethyl group, a chloroethyl group or a hydroxyethyl group.)

[0061]

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Or

[0063]

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( ^Wherein R ^g7 , R ^g8 and R ^g9 are the same or different and each represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, an alkoxy group, an aryl group or an aralkyl group). Shows the group to be formed. (CG5) dithioketopyrrolopyrrole pigment

[0065]

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( ^Wherein R ^g10 and R ^g11 are the same or different and represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and R ^g12 and R ^g13 are the same or different and are a hydrogen atom, an alkyl group or an aryl group. (CG6) Metal-free naphthalocyanine pigment

[0067]

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( ^Wherein R ^g14 , R ^g15 , R ^g16 and R ^g14
g17 is the same or different and represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. (CG7) Metal naphthalocyanine pigment

[0069]

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( ^Wherein R ^g18 , R ^g19 , R ^g20 and R ^g20
g21 is the same or different and represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and M represents Ti or V. ) (CG8) Squaraine pigment

[0071]

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( ^Wherein R ^g22 and R ^g23 are the same or different and each represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom.) (CG9) Trisazo pigment

[0073]

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(Wherein Cp ³ , Cp ⁴ and Cp ⁵ are the same or different and represent a coupler residue.) (CG10) Indigo pigment

[0075]

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( ^Wherein , R ^g24 and R ^g25 are the same or different and each represent a hydrogen atom, an alkyl group or an aryl group, and Z represents an oxygen atom or a sulfur atom.) (CG11) Azulhenium pigment

[0077]

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( ^Wherein R ^g26 and R ^g27 are the same or different and each represent a hydrogen atom, an alkyl group or an aryl group.) (CG12) Cyanine pigment

[0079]

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(In the formula, R ^g28 and R ^g29 are the same or different and each represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and R ^g30 and R ^g31 are the same or different and represent a hydrogen atom, an alkyl group or an aryl group. Represents a group.) In the above-described charge generating agent, as the alkyl group,
In addition to the groups described above, groups having 5 to 6 carbon atoms such as n-pentyl and n-hexyl are included. The substituted or unsubstituted alkyl group having 18 or less carbon atoms is a group containing heptyl, octyl, nonyl, decyl, dodecyl, tridecyl, pentadecyl, octadecyl and the like in addition to the alkyl group having 1 to 6 carbon atoms. Examples of the cycloalkyl group include those having 3 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
To 8 groups. Examples of the alkoxy group include groups having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, t-butoxy, n-pentyloxy, and n-hexyloxy. Examples of the aryl group include phenyl, naphthyl, anthryl,
And groups such as phenanthryl. As aralkyl groups, for example, benzyl, benzhydryl, phenethyl,
And groups such as trityl. Examples of the alkanoyl group include formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl and the like. Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, 2H-imidazolyl, pyrazolyl, triazolyl,
Examples include tetrazolyl, pyranyl, pyridyl, piperidyl, piperidino, 3-morpholinyl, morpholino, and thiazolyl. Further, it may be a heterocyclic group condensed with an aromatic ring.

The substituent which may be substituted on the above group includes
For example, a halogen atom, an amino group, a hydroxyl group, a carboxyl group which may be esterified, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and 2 to 2 carbon atoms which may have an aryl group And 6 alkenyl groups. Cp ¹ , Cp ² , Cp ³ , Cp ⁴ and Cp
Examples of the coupler residue represented by ⁵ include groups represented by the following general formulas (Cp-1) to (Cp-11).

[0083]

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[0084]

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In each formula, R ^g32 represents a carbamoyl group, a sulfamoyl group, an allofanoyl group, an oxamoyl group, an anthraniloyl group, a carbazoyl group, a glycyl group, a hydantoyl group, a phthalamoyl group or a succinamoyl group. These groups include a halogen atom, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a nitro group, a cyano group, an alkyl group, an alkenyl group,
It may have a substituent such as a carbonyl group or a carboxyl group.

R ^g33 represents an atomic group necessary for forming an aromatic ring, a polycyclic hydrocarbon or a heterocyclic ring by condensing with a benzene ring, and these rings have the same substituents as described above. You may. R ^g34 represents an oxygen atom, a sulfur atom or an imino group. R ^g35 represents a divalent chain hydrocarbon group or an aromatic hydrocarbon group, and these groups may have the same substituent as described above.

R ^g36 represents an alkyl group, an aralkyl group, an aryl group or a heterocyclic group, and these groups may have the same substituent as described above. R ^g37 is required to form a heterocyclic ring together with a divalent chain hydrocarbon group or an aromatic hydrocarbon group, or with two nitrogen atoms in the above groups (Cp-1) to (Cp-11). Represents an atomic group, and these rings may have the same substituents as described above.

R ^g38 represents a hydrogen atom, an alkyl group, an amino group, a carbamoyl group, a sulfamoyl group, an allophanoyl group, a carboxyl group, an alkoxycarbonyl group, an aryl group or a cyano group, and the groups other than the hydrogen atom are the same as those described above. It may have a substituent. R ^g39 represents an alkyl group or an aryl group, and these groups may have the same substituent as described above.

Examples of the alkenyl group include those having 2 to 2 carbon atoms such as vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, 2-pentenyl and 2-hexenyl.
And 6 alkenyl groups. In the above R ^g33 ,
Examples of the atomic group necessary to form an aromatic ring by condensing with a benzene ring include an alkylene group having 1 to 4 carbon atoms such as methylene, ethylene, trimethylene, and tetramethylene.

Examples of the aromatic ring formed by the condensation of R ^g33 and a benzene ring include a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a chrysene ring, and a naphthacene ring. In R ^g33 , the atomic group necessary for condensing with a benzene ring to form a polycyclic hydrocarbon includes, for example, the alkylene group having 1 to 4 carbon atoms, or a carbazole ring, a benzocarbazole ring, or a dibenzofuran ring. And the like.

In R ^g33 , the atomic groups necessary for condensing with a benzene ring to form a heterocyclic ring include, for example, benzofuranyl, benzothiophenyl, indolyl,
H-indolyl, benzoxazolyl, benzothiazolyl, 1H-indolyl, benzimidazolyl, chromenil, chromanil, isochromanyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazonyril, quinoxalinyl, dibenzofuranyl, carbazolyl, xanthenyl, acridinyl, phenanthrinyl Phenazinyl, phenoxazinyl, thianthrenyl and the like can be mentioned.

Examples of the aromatic heterocyclic group formed by the condensation of R ^g33 with a benzene ring include thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, and pyridyl. And thiazolyl. Further, it may be a heterocyclic group condensed with another aromatic ring (for example, benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, quinolyl and the like).

In R ^g35 and R ^g37 , ^examples of the divalent chain hydrocarbon group include ethylene, trimethylene, and tetramethylene, and examples of the divalent aromatic hydrocarbon group include phenylene, naphthylene, and phenanthrylene. Is raised. In the above R ^g36 , as the heterocyclic group,
Pyridyl, pyrazyl, thienyl, pyranyl, indolyl and the like.

In R ^g37 , the atomic groups necessary for forming a heterocyclic ring with two nitrogen atoms include, for example, phenylene, naphthylene, phenanthrylene, ethylene, trimethylene, tetramethylene and the like. Examples of the aromatic heterocyclic group formed by the above R ^g37 and two nitrogen atoms include benzimidazole, benzo [f] benzimidazole, dibenzo [e, g] benzimidazole, benzopyrimidine and the like. .
These groups may have the same substituents as described above.

In R ^g38 , ^examples of the alkoxycarbonyl group include groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and butoxycarbonyl. In the present invention, in addition to the above-exemplified charge generating agents, for example, powders of inorganic photoconductive materials such as selenium, selenium-tellurium, selenium-arsenic, cadmium sulfide, amorphous silicon, pyrylium salts, anthanthrone-based pigments, Conventionally known charge generators such as phenylmethane pigments, sllen pigments, toluidine pigments, pyrazoline pigments, and quinacridone pigments can be used.

The charge generating agents exemplified above are used alone or in combination of two or more so as to have an absorption wavelength in a desired region. Among the above-described charge generating agents, a photoreceptor having sensitivity in a wavelength region of 700 nm or more is required for a digital optical image forming apparatus such as a laser beam printer or a facsimile using a light source such as a semiconductor laser. Therefore, for example, phthalocyanine pigments such as metal-free phthalocyanine represented by the general formula (CG1) and oxotitanyl phthalocyanine represented by the general formula (CG2) are preferably used. The crystal form of the phthalocyanine pigment is not particularly limited, and various types can be used.

On the other hand, an image forming apparatus of an analog optical system such as an electrostatic copying machine using a white light source such as a halogen lamp requires a photosensitive member having sensitivity in a visible region. Perylene pigments represented by (CG3), bisazo pigments represented by general formula (CG4), and the like are preferably used. << Hole Transport Agent >> In the electrophotographic photoreceptor of the present invention, together with the stilbene derivative (1), (2) of the present invention which is a hole transport agent, other conventionally known hole transport agents are contained in the photosensitive layer. May be.

As such a hole transporting agent, various compounds having a high hole transporting ability, for example, a compound represented by the following general formula (HT1):
And a compound represented by (HT13). (HT1)

[0099]

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(Wherein, R ^h1 , R ^h2 , R ^h3 , R ^h4 , R ^h5 and R ^h6 are the same or different and each have a halogen atom, an alkyl group which may have a substituent, A and b are the same or different and represent an integer of 0 to 4, and c, d, e and f are the same or different and represent 0 to 5 of an aryl group which may have a substituent. When a, b, c, d, e or f is 2 or more, each of R ^h1 , R ^h2 , R ^h3 , R ^h4 , R ^h5 and R ^h6
May be different. ) (HT2)

[0101]

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(Wherein R ^h7 , R ^h8 , R ^h9 , R ^h10 and R ^h11 are the same or different and each is a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, An aryl group which may have a group or a substituent is shown.
g, h, i and j are the same or different and each represents an integer of 0 to 5, and k represents an integer of 0 to 4. Note that g, h, i,
When j or k is 2 or more, each of R ^h7 , R ^h8 , R ^h9 , R
^h10 and R ^h11 may be different. ) (HT3)

[0103]

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(Wherein R^h12, R^h13, R^h14And R
^h15Are the same or different and have a halogen atom and
Alkyl group which may be substituted, alkoxy which may have a substituent
It represents an aryl group which may have a substituent or a substituent. R
^h16Has a halogen atom, cyano group, nitro group,
Alkyl group which may be substituted, alkoxy which may have a substituent
It represents an aryl group which may have a substituent or a substituent.
m, n, o and p are the same or different, and
Indicates a number. q shows the integer of 0-6. Note that m, n,
When o, p or q is 2 or more, each R^h12, R^h13, R
^h14, R^h15And R ^h16May be different. ) (HT4)

[0105]

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^Wherein R ^h17 , R ^h18 , R ^h19 and R ^h17
h20 is the same or different and represents a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent or an aryl group which may have a substituent.
r, s, t and u are the same or different and each represent an integer of 0-5. When r, s, t or u is 2 or more,
Each of R ^h17 , R ^h18 , R ^h19 and R ^h20 may be different. ) (HT5)

[0107]

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(In the formula, R ^h21 and R ^h22 are the same or different and each represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. R ^h23 , R ^h24 , R ^h25 and R ^h22
h26 is the same or different and represents a hydrogen atom, an alkyl group or an aryl group. ) (HT6)

[0109]

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( ^Wherein R ^h27 , R ^h28 and R ^h29 are the same or different and each represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group). (HT7)

[0111]

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( ^Wherein R ^h30 , R ^h31 , R ^h32 and R ^h30)
h33 is the same or different and is a hydrogen atom, a halogen atom,
It represents an alkyl group or an alkoxy group. ) (HT8)

[0113]

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( ^Wherein R ^h34 , R ^h35 , R ^h36 , R ^h37
And R ^h38 are the same or different and each represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. ) (HT9)

[0115]

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[0116] (wherein, R ^H39 represents a hydrogen atom or an alkyl group, R ^h40, R ^h41 and R ^{h4 2} are the same or different and represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group.) (HT10 )

[0117]

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[0118] (wherein, R ^h43, R ^h44 and R ^h45 are the same or different and represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group.) (HT11)

[0119]

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(In the formula, R ^h46 and R ^h47 are the same or different and each represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent or an alkoxy group which may have a substituent. R ^h48 And R ^h49 are the same or different,
It represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent. ) (HT12)

[0121]

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(Wherein R^h50, R^h51, R^h52,
R^h53, R^h54And R^h55Are the same or different
Alkyl group which may have a substituent, may have a substituent
An alkoxy group or an aryl group which may have a substituent;
Show. α represents an integer of 1 to 10, and v, w, x, y, z
And β are the same or different and represent an integer of 0 to 2. What
When v, w, x, y, z or β is 2, each
R^h50, R^h51, R^h52, R^h53, R ^h54And R^h55
May be different. ) (HT13)

[0123]

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( ^Wherein R ^h56 , R ^h57 , R ^h58 and R ^h58)
h59 is the same or different and is a hydrogen atom, a halogen atom,
Represents an alkyl group or an alkoxy group, and Φ represents the following formula:

[0125]

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Represents the group (Φ-1), (Φ-2) or (Φ-3). In the above-described hole transporting agent, the alkyl group, the alkoxy group, the aryl group, the aralkyl group, and the halogen atom include the same groups as described above. Examples of the substituent that may be substituted on the above group include a halogen atom, an amino group, a hydroxyl group, an optionally esterified carboxyl group, a cyano group, an alkyl group having 1 to 6 carbon atoms,
And an alkenyl group having 2 to 6 carbon atoms which may have 6 alkoxy groups and aryl groups. The substitution position of the substituent is not particularly limited.

Further, the above-described hole transporting agents (HT1) to (HT1)
With or in place of 3), a conventionally known hole transporting substance, that is, an oxadiazole-based compound such as 2,5-di (4-methylaminophenyl) -1,3,4-oxadiazole, 9 Styryl compounds such as-(4-diethylaminostyryl) anthracene, carbazole compounds such as polyvinylcarbazole, organic polysilane compounds, pyrazoline compounds such as 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline, hydrazone compounds, Nitrogen-containing cyclic compounds such as triphenylamine compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, triazole compounds, and condensed polycyclic compounds Compounds and the like can also be used.

In the present invention, only one hole transporting agent may be used, or two or more hole transporting agents may be used in combination. Also,
When a hole transporting agent having a film-forming property such as polyvinyl carbazole is used, a binder resin is not necessarily required. << Electron Transport Agent >> Examples of the electron transport agent used in the present invention include various compounds having high electron transport ability, for example, compounds represented by the following general formulas (ET1) to (ET17).

(ET1)

[0130]

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(Wherein, R ^e1 , R ^e2 , R ^e3 , R ^e4 and R
^e5 are the same or different, a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent,
It represents an aryl group which may have a substituent, an aralkyl group which may have a substituent, a phenoxy group which may have a substituent, or a halogen atom. ) (ET2)

[0132]

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(Where R ^e6 is an alkyl group, R ^e7 is an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, Represents an aralkyl group, a halogen atom or a halogenated alkyl group which may have a group, γ represents an integer of 0 to 5. When γ is 2 or more, each ^{Re 7} may be different from each other. ) (ET3)

[0134]

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(Wherein R ^e8 and R ^e9 are the same or different and each represents an alkyl group. Δ is an integer of 1 to 4,
Represents an integer of 0 to 4. Note that when δ and ε is 2 or more, each R ^e8 and R ^e9 may be different. ) (ET4)

[0136]

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(In the formula, R ^e10 represents an alkyl group, an aryl group, an aralkyl group, an alkoxy group, a halogenated alkyl group or a halogen atom.
Indicates an integer. When η is 2 or more, each ^{Re 10} may be different. ) (ET5)

[0138]

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(In the formula, R ^e11 represents an alkyl group, and σ represents an integer of 1 to 4. When σ is 2 or more, each R
^e11 may be different. ) (ET6)

[0140]

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(In the formula, R ^e12 and R ^e13 are the same or different and each represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyloxycarbonyl group, an alkoxy group, a hydroxyl group, a nitro group, or a cyano group. It represents an oxygen atom, a = N-CN group or a = C (CN) ₂ group.) (ET7)

[0142]

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( ^Wherein R ^e14 represents a hydrogen atom, a halogen atom, an alkyl group or a phenyl group which may have a substituent, and R ^e15 represents a halogen atom, an alkyl group which may have a substituent or Represents a phenyl group, an alkoxycarbonyl group, an N-alkylcarbamoyl group, a cyano group or a nitro group which may have a group, and λ represents an integer of 0 to 3.
When λ is 2 or more, each ^{Re 15} may be different from each other. ) (ET8)

[0144]

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(In the formula, θ represents an integer of 1 to 2.) (ET9)

[0146]

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(In the formula, R ^e16 and R ^e17 are the same or different and each represent a halogen atom, an alkyl group which may have a substituent, a cyano group, a nitro group, or an alkoxycarbonyl group. shows a third integer. Note, [nu or ξ is when 2 or more, each R ^e16 and R ^e17 may be different from each other.) (ET10)

[0148]

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(In the formula, R ^e18 and R ^e19 are the same or different and each represents a phenyl group, a condensed polycyclic group or a heterocyclic group, and these groups may have a substituent.) ET11)

[0150]

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( ^Wherein R ^e20 represents an amino group, a dialkylamino group, an alkoxy group, an alkyl group or a phenyl group, and π represents an integer of 1-2. When π is 2,
Each R ^{e2 0} may be different from each other. ) (ET12)

[0152]

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( ^Wherein R ^e21 represents a hydrogen atom, an alkyl group,
It represents an aryl group, an alkoxy group or an aralkyl group. ) (ET13)

[0154]

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^Wherein R ^e22 represents a halogen atom, an alkyl group which may have a substituent, a phenyl group which may have a substituent, an alkoxycarbonyl group, an N-alkylcarbamoyl group, a cyano group or a nitro group. Represents an integer of 0 to 3. When μ is 2 or more, each ^{Re 22} may be different from each other.) (ET14)

[0156]

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[0157] (wherein, R ^e23 is a alkyl group or a substituted group may have a substituent indicates also aryl group, R ^e24 represents an alkyl group which may have a substituent, may have an aryl group or a group:. showing a ^-O-R e24a R e24a in the group, represents an aryl group which may have a an optionally substituted alkyl group or a substituted group .) (ET15)

[0158]

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[0159] (In the ^{formula, R e25, R e26, R} e27,
R ^e28, R ^e29, R ^e30 and R ^e31 represents an alkyl group, an aryl group, an aralkyl group, an alkoxy group, a halogen atom or a halogenated alkyl group the same or different. χ and φ are the same or different and represent an integer of 0 to 4. ) (ET16)

[0160]

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(In the formula, R ^e32 and R ^e33 are the same or different and represent an alkyl group, an aryl group, an alkoxy group, a halogen atom or a halogenated alkyl group. Τ and ψ are the same or different and are each an integer of 0-4. (ET17)

[0162]

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^Wherein R ^e34 , R ^e35 , R ^e36 and R
^e37 represents the same or different and represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a cycloalkyl group or an amino group. However, R ^e34 , R ^e35 , R
^At least two of ^e36 and ^Re37 are the same group other than a hydrogen atom. In the electron transporting agent exemplified above, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a cycloalkyl group,
Examples of the alkoxycarbonyl group, the heterocyclic group, and the halogen atom include the same groups as described above.

Examples of the alkyl group and the halogen atom in the halogenated alkyl group include the same groups as described above. Examples of the condensed polycyclic group include naphthyl, phenanthryl, anthryl and the like. Examples of the aralkyloxycarbonyl group include those in which the aralkyl moiety is any of the various aralkyl groups described above. Examples of the N-alkylcarbamoyl group include those in which the alkyl moiety is any of the various alkyl groups described above. Examples of the dialkylamino group include those in which the alkyl moiety is any of the various alkyl groups described above. Substitute for amino 2
The two alkyls may be the same or different.

Examples of the substituent which may be substituted on each of the above groups include a halogen atom, an amino group, a hydroxyl group, a carboxyl group which may be esterified, a cyano group, an alkyl group having 1 to 6 carbon atoms and a carbon atom having 1 to 6 carbon atoms. Examples thereof include an alkoxy group having 1 to 6 carbon atoms and an alkenyl group having 2 to 6 carbon atoms which may have an aryl group. The substitution position of the substituent is not particularly limited.

In the present invention, in addition to the above examples, conventionally known electron transporting substances, for example, benzoquinone compounds, malononitriles, thiopyran compounds, tetracyanoethylene, 2,4,8-trinitrothioxanthone, dinitrobenzene, Dinitroanthracene, dinitroacridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, maleic anhydride, dibromomaleic anhydride and the like can be used.

In the present invention, only one electron transport agent may be used, or two or more electron transport agents may be used in combination. << Binder Resin >> As the binder resin for dispersing the above components, various resins conventionally used in the photosensitive layer can be used. For example, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-
Maleic acid copolymer, acrylic copolymer, styrene-acrylic acid copolymer, polyethylene, ethylene-vinyl acetate copolymer, chlorinated polyethylene, polyvinyl chloride, polypropylene, ionomer, vinyl chloride-vinyl acetate copolymer, Polyester, alkyd resin, polyamide,
Thermoplastic resins such as polyurethane, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin, polyester resin; silicone resin, epoxy resin, phenol resin, urea resin, melamine resin, and other crosslinkable Thermosetting resin; resins such as photo-curable resins such as epoxy acrylate and urethane-acrylate can be used.

In the photosensitive layer, in addition to the above-mentioned components, various additives known in the art, such as an antioxidant, a radical scavenger, a singlet quencher, and an ultraviolet absorber as long as they do not adversely affect the electrophotographic properties. Agents, softeners, plasticizers, surface modifiers, extenders, thickeners, dispersion stabilizers, waxes, acceptors, donors, and the like.
Further, in order to improve the sensitivity of the photosensitive layer, a known sensitizer such as terphenyl, halonaphthoquinones, acenaphthylene and the like may be used in combination with the charge generator.

In the single-layer type photoreceptor, the charge generating agent may be blended in an amount of 0.1 to 50 parts by weight, preferably 0.5 to 30 parts by weight, based on 100 parts by weight of the binder resin. The stilbene derivatives (1) and (2) (hole transporting agent) of the present invention may be blended in an amount of 20 to 500 parts by weight, preferably 30 to 200 parts by weight, based on 100 parts by weight of the binder resin. When an electron transporting agent is contained, the proportion of the electron transporting agent is suitably 5 to 100 parts by weight, preferably 10 to 80 parts by weight, based on 100 parts by weight of the binder resin. The thickness of the photosensitive layer in the single-layer type photosensitive member is 5 to 100 μm, preferably 10 to 50 μm.

In the laminate type photoreceptor, the charge generating agent and the binder resin constituting the charge generating layer can be used in various ratios, but the charge generating agent is added to 100 parts by weight of the binder resin. It is appropriate to mix at a ratio of １０００1000 parts by weight, preferably 30-500 parts by weight. When the charge generating layer contains a hole transporting agent, the proportion of the hole transporting agent is suitably from 10 to 500 parts by weight, preferably from 50 to 200 parts by weight, based on 100 parts by weight of the binder resin. .

The hole transporting agent and the binder resin constituting the charge transporting layer can be used in various ratios within a range that does not hinder charge transport and a range that does not crystallize. The stilbene derivatives (1) and (2) (hole transporting agent) of the present invention are used in an amount of 10 to 500 parts by weight, preferably 25 parts by weight, based on 100 parts by weight of the binder resin, so that the charges generated in the above can be easily transported. It is appropriate to mix at a ratio of ~ 200 resin. When the charge transporting layer contains an electron transporting agent, the proportion of the electron transporting agent is suitably 5 to 200 parts by weight, preferably 10 to 100 parts by weight, per 100 parts by weight of the binder resin.

The thickness of the photosensitive layer in the laminated photoreceptor is such that the charge generation layer has a thickness of about 0.01 to 5 μm, preferably 0.1 to 5 μm.
The thickness is about 3 μm, and the thickness of the charge transport layer is about 2 to 100 μm, preferably about 5 to 50 μm. In the case of a single-layer type photoreceptor, between the conductive substrate and the photosensitive layer, and in the case of the laminated type photoreceptor, between the conductive substrate and the charge generating layer, between the conductive substrate and the charge transport layer, or A barrier layer may be formed between the generation layer and the charge transport layer as long as the characteristics of the photoreceptor are not impaired. Further, a protective layer may be formed on the surface of the photoconductor.

As the conductive substrate on which the photosensitive layer is formed, various conductive materials can be used.
For example, iron, aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, brass and other simple metals, and plastic materials on which the above metals are deposited or laminated, Glasses coated with aluminum iodide, tin oxide, indium oxide, and the like can be given.

The shape of the conductive substrate may be sheet-like or drum-like depending on the structure of the image forming apparatus to be used. The substrate itself has conductivity or the surface of the substrate has conductivity. What is necessary is just to have the property. The conductive substrate preferably has a sufficient mechanical strength when used. When the photosensitive layer is formed by a coating method, a charge generating agent, a charge transporting agent, a binder resin, and the like described above, together with a suitable solvent, may be used in a known manner, for example, a roll mill, a ball mill, an attritor, a paint shaker, or What is necessary is just to disperse and mix using a sonic disperser or the like to prepare a dispersion, apply it by a known means, and dry it.

As the solvent for preparing the dispersion, various organic solvents can be used, for example, alcohols such as methanol, ethanol, isopropanol and butanol; and aliphatic carbons such as n-hexane, octane and cyclohexane. Hydrogen; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether Ketones such as acetone, methyl ethyl ketone and cyclohexanone; esters such as ethyl acetate and methyl acetate; dimethyl formaldehyde, dimethyl formamide, dimethyl sulfo Sid and the like. These solvents are used alone or in combination of two or more.

Further, in order to improve the dispersibility of the charge transporting agent and the charge generating agent and the smoothness of the surface of the photosensitive layer, a surfactant is used.
A leveling agent or the like may be used.

[0177]

The present invention will be described below with reference to Synthesis Examples, Examples and Comparative Examples. << Synthesis of Stilbene Derivative >> Reference Example 1 (Synthesis of 4-isopropyltriphenylamine) 19.4 g (143 mmol) of 4-isopropylaniline, 60 g (294 mmol) of iodobenzene, 20 g (145 mmol) of anhydrous potassium carbonate and powdered copper 1
g (16 mmol) was added to 150 ml of nitrobenzene and reacted under reflux for about 24 hours. After the reaction,
The inorganic salt was removed and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / hexane mixed solvent) to give the title compound 2
9.2 g were obtained (yield 71%).

Reference Example 2 (Synthesis of 4-isopropyl-4'-formyltriphenylamine) 28 g (97 mmol) of 4-isopropyltriphenylamine was dissolved in 300 ml of dimethylformamide (DMF), and 15 g of phosphoric acid oxychloride ( 98 mmol) and reacted at 40 ° C. for 1 hour. After the reaction, water 3
It was added to 00 ml and extracted with ethyl acetate. Next, the organic layer was washed with water and dried to distill off the solvent, and the residue was purified by silica gel column chromatography (developing solvent: mixed solvent of chloroform / hexane) to give the title compound.
7 g (87% yield) were obtained.

Reference Example 3 (Synthesis of 3,4-dimethyltriphenylamine) In the same manner as in Reference Example 1, except that 4-isopropylaniline was replaced by 17.4 g (144 mmol) of 3,4-xylidine. After performing reaction and purification, the title compound 29.4 was obtained.
g was obtained (75% yield). Reference Example 4 (Synthesis of 3,4-dimethyl-4'-formyltriphenylamine) Instead of 4-isopropyltriphenylamine, 3,4-
Reference Example 2 except that dimethyltriphenylamine was used
The reaction and purification were carried out in the same manner as in the above to give 25.2 g of the title compound.
Was obtained (88% yield).

Reference Example 5 (Synthesis of bisphosphate ester) A bisphosphate ester derivative represented by the following formula (94p) was obtained from triethyl phosphate and p-xylylenedichloride. Further, a bisphosphate ester derivative represented by the following formula (94m) was obtained from triethyl phosphate and m-xylylene dichloride.

[0181]

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Synthesis Example 1 (Synthesis of stilbene derivative (11-4)) 5 g of bisphosphate ester represented by the above formula (94p) (1
3.2 millimils) and degassed and dried sodium hydride
1 g (27.5 mmol) with tetrahydrofuran 25
It was added to 0 ml and cooled with ice. To this, 8.4 g of 4-isopropyl-4'-formyltriphenylamine dissolved in 50 ml of tetrahydrofuran was added dropwise and reacted at room temperature for about 3 hours. After the reaction, the reaction solution was added to about 2% of a diluted aqueous hydrochloric acid solution (400 ml), and the precipitated crystals were filtered and washed with water. After the crystals were dried, the crystals were purified by silica gel column chromatography (developing solvent: mixed solvent of chloroform / hexane).
6.6 g of the stilbene derivative shown in No. 4 was obtained (yield: 71).
%).

Melting point: 120 to 122 ° C. The ¹ H-NMR spectrum of the above stilbene derivative (11-4) is shown in FIG. 1, and the infrared absorption spectrum is shown in FIG. Synthesis Example 2 (Synthesis of stilbene derivative (12-4)) Instead of the bisphosphate represented by the above formula (94p),
The reaction and purification were carried out in the same manner as in Synthesis Example 1 except that 5 g of the bisphosphate ester represented by the above formula (94m) was used, and 5.4 g of the stilbene derivative represented by Compound No. 12-4 in Table 1 was obtained. (58% yield).

Melting point: 94-96 ° C. The ¹ H-NMR spectrum of the above stilbene derivative (12-4) is shown in FIG. 3, and the infrared absorption spectrum is shown in FIG. Synthesis Example 3 (Synthesis of stilbene derivative (11-8)) In place of 4-isopropyl-4'-formyltriphenylamine, 8 g (26.5 mmol) of 3,4-dimethyl-4'-formyltriphenylamine was used. Other than using
The reaction and purification were carried out in the same manner as in Synthesis Example 1, and the stilbene derivative represented by Compound No. 11-8 in Table 2 above.
7 g was obtained (75% yield).

Melting point: 195 to 197 ° C. The ¹ H-NMR spectrum of the above stilbene derivative (11-8) is shown in FIG. 5, and the infrared absorption spectrum is shown in FIG. Synthesis Example 4 (Synthesis of stilbene derivative (12-8)) Instead of bisphosphate represented by the above formula (94p),
The reaction and purification were carried out in the same manner as in Synthesis Example 3 except that 5 g of the bisphosphate ester represented by the above formula (94m) was used, and 4.6 g of the stilbene derivative represented by the compound number 12-8 in Table 2 was obtained. (52% yield).

Melting point: 88-90 ° C. ¹ H-NMR spectrum and infrared absorption spectrum of the stilbene derivative (12-8) are shown in FIG. 7 and FIG. Synthesis Example 5 (Synthesis of stilbene derivative (11-2)) Instead of 4-isopropyl-4'-formyltriphenylamine, 8 g (26.5 mmol) of 4-ethyl-4'-formyltriphenylamine was used. Otherwise, the reaction and purification were carried out in the same manner as in Synthesis Example 1 to obtain 7.8 g of a stilbene derivative represented by Compound No. 11-2 in Table 1 (yield: 87%).

Melting point: 186 to 188 ° C. The ¹ H-NMR spectrum of the above stilbene derivative (11-2) is shown in FIG. 9, and the infrared absorption spectrum is shown in FIG. Synthesis Example 6 (Synthesis of stilbene derivative (11-5)) Instead of 4-isopropyl-4'-formyltriphenylamine, 8.8 g of 4- (n-butyl) -4'-formyltriphenylamine (26. The reaction and purification were carried out in the same manner as in Synthesis Example 1 except that 7 mmol) was used to obtain 7.7 g of a stilbene derivative represented by Compound No. 11-5 in Table 1 (yield 79%).

Melting point: 229 ° -231 ° C. FIG. 11 shows the ¹ H-NMR spectrum of the above stilbene derivative (11-5), and FIG. 12 shows its infrared absorption spectrum. Synthesis Example 7 (Synthesis of stilbene derivative (11-15)) Instead of 4-isopropyl-4'-formyltriphenylamine, 8.8 g of 4- (s-butyl) -4'-formyltriphenylamine (26. The reaction and purification were carried out in the same manner as in Synthesis Example 1 except for using 7 mmol) to obtain 7.6 g of a stilbene derivative represented by Compound No. 11-15 in Table 2 (yield 78%).

Melting point: 188-190 ° C. FIG. 13 shows the ¹ H-NMR spectrum of the above stilbene derivative (11-15), and FIG. 14 shows its infrared absorption spectrum. Synthesis Example 8 (Synthesis of stilbene derivative (11-3)) Instead of 4-isopropyl-4'-formyltriphenylamine, 8.4 g of 4- (n-propyl) -4'-formyltriphenylamine (26. The reaction and purification were carried out in the same manner as in Synthesis Example 1 except that 6 mmol) was used to obtain 7.5 g of a stilbene derivative represented by Compound No. 11-3 in Table 1 (yield: 80%).

Melting point: 236 to 238 ° C. FIG. 15 shows the ¹ H-NMR spectrum of the stilbene derivative (11-3), and FIG. 16 shows the infrared absorption spectrum. Synthesis Example 9 (Synthesis of stilbene derivative (21-1)) Instead of 4-isopropyl-4'-formyltriphenylamine, 8.4 g of 2,4,6-trimethyl-4'-formyltriphenylamine (26. The reaction and purification were carried out in the same manner as in Synthesis Example 1 except that 6 mmol) was used to obtain 7.2 g of the stilbene derivative represented by Compound No. 21-1 in Table 3 (yield: 77%).

Melting point: 226-228 ° C. FIG. 17 shows the ¹ H-NMR spectrum of the stilbene derivative (21-1), and FIG. 18 shows the infrared absorption spectrum. Synthesis Example 10 (Synthesis of stilbene derivative (22-1)) Instead of the bisphosphate represented by the above formula (94p),
The reaction and purification were carried out in the same manner as in Synthesis Example 9 except for using 5 g of the bisphosphate ester represented by the above formula (94m), and 5.6 g of the stilbene derivative represented by the compound number 22-1 in Table 3 was obtained. (60% yield).

Melting point: 95-97 ° C. Synthesis Example 11 (Synthesis of stilbene derivative (21-3)) Instead of 4-isopropyl-4′-formyltriphenylamine, 2,4,6-tri (t-butyl) Reaction and purification were carried out in the same manner as in Synthesis Example 1 except that 11.7 g (26.5 mmol) of -4'-formyltriphenylamine was used, and the stilbene derivative represented by Compound No. 21-3 in Table 3 above 9.2 g were obtained (73% of yield).

Melting point: 230-232 ° C. Synthesis Example 12 (Synthesis of stilbene derivative (22-4)) Instead of 4-isopropyl-4′-formyltriphenylamine, 2,3,4,5,6-pentamethyl- 4'-
The reaction and purification were carried out in the same manner as in Synthesis Example 2 except that 9.1 g (26.5 mmol) of formyltriphenylamine was used, and 6.8 g of the stilbene derivative represented by Compound No. 22-4 in Table 3 was obtained. (68% yield).

Melting point: 94-96 ° C. << Manufacture of electrophotographic photoreceptor >> (Single-layer type photoreceptor for digital light source) Example 1 X-type non-metallic phthalocyanine (CG1-1) was used as a charge generating agent. The hole transporting agents include the compound number 11-2 in Table 1 above.
A stilbene derivative represented by the following formula was used.

5 parts by weight of the above-described charge generating agent, 10 parts of the hole transporting agent
0 parts by weight and 100 parts by weight of a binder resin (polycarbonate) were mixed and dispersed in a ball mill for 50 hours together with 800 parts by weight of a solvent (tetrahydrofuran) to prepare a coating solution for a single-layer type photosensitive layer. Next, this coating solution is applied onto a conductive substrate (aluminum tube) by dip coating, and dried with hot air at 100 ° C. for 30 minutes to form a single layer for a digital light source having a single-layer photosensitive layer having a thickness of 25 μm. A layer type photoreceptor was manufactured.

Example 2 A single-layer photoreceptor for a digital light source was prepared in the same manner as in Example 1, except that the stilbene derivative represented by the compound number 11-4 in Table 1 was used as the hole transporting agent. Manufactured. Example 3 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 1, except that the stilbene derivative represented by the compound number 12-4 in Table 1 was used as the hole transporting agent.

Example 4 A single-layer photoreceptor for a digital light source was prepared in the same manner as in Example 1, except that the stilbene derivative represented by the compound number 11-8 in Table 1 was used as the hole transporting agent. Manufactured. Example 5 In a coating solution for a single-layer type photosensitive layer, an electron transporting agent represented by the following formula (ET17-1):

[0198]

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A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Example 1, except that 30 parts by weight of the diphenoquinone derivative represented by the formula (1) was blended. Example 6 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 5, except that the stilbene derivative (11-4) was used as a hole transporting agent.

Example 7 A single-layer type photoreceptor for a digital light source was produced in the same manner as in Example 5, except that the stilbene derivative (12-4) was used as the hole transporting agent. Example 8 A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Example 5, except that the stilbene derivative (11-8) was used as the hole transporting agent.

Examples 9 to 12 As an electron transporting agent, a compound represented by the formula (ET14-1):

[0202]

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A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 5 to 8, except that the naphthoquinone derivative represented by the formula (1) was used. Examples 13 to 16 As an electron transporting agent, a compound represented by the formula (ET14-2):

[0204]

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A single-layer type photoreceptor for a digital light source was manufactured in the same manner as in Examples 5 to 8 except that the naphthoquinone derivative represented by the following formula was used. Comparative Example 1 As a hole transporting agent, a compound represented by the formula (2-1):

[0206]

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A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Example 1 except that the stilbene derivative represented by the following formula was used. Comparative Example 2 Formula (2-2):

[0208]

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A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Example 1 except that the stilbene derivative represented by the following formula was used. Comparative Example 3 As a hole transporting agent, a compound represented by the formula (2-3):

[0210]

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In addition to using a stilbene derivative represented by
Is a single-layer photosensitive for a digital light source in the same manner as in Example 1.
Body manufactured. Examples 1 to 16 and Comparative Examples 1 to 3
The following electrical property test (I) was performed on the photoconductor obtained in
The electrical characteristics of each photoreceptor were evaluated. Electrical property test (I) Using a drum sensitivity tester manufactured by GENTEC
A voltage is applied to the surface of each photoconductor by applying
After charging to 0 ± 20V, the surface potential V_oMeasure (V)
did. Next, the white light of the halogen lamp
Wavelength 780 extracted from the hologram using a band-pass filter
nm monochromatic light (half-width 20 nm, light intensity 8 μJ / c
m^Two) Onto the surface of the photoconductor (irradiation time 1.5 seconds)
And the surface potential V_oThe time it took for the
Measured, half-exposure E_1/2(ΜJ / cm ^Two)
Was. In addition, the surface at the time of 0.5 seconds after the start of exposure
Potential is residual potential V_rIt was measured as (V).

Table 5 shows the types of the charge generating agent, the hole transporting agent and the electron transporting agent used in each of the above Examples and Comparative Examples, and the test results of the electrical characteristics. In the following tables, the types of the charge generating agent, the hole transporting agent and the electron transporting agent are indicated by the respective formula numbers or the numbers assigned to the compounds.

[0213]

[Table 5]

Examples 17 to 20 α-oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was produced in the same manner as in Examples 1 to 4, except that G2-1) was used. Examples 21 to 24 As an electric charge generating agent, α-oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 5 to 8, except that G2-1) was used.

Examples 25 to 28 α-oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 9 to 12, except that G2-1) was used. Examples 29 to 32 α-oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was produced in the same manner as in Examples 13 to 16, except that G2-1) was used.

Comparative Examples 4 to 6 α-oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Comparative Examples 1 to 3, except that G2-1) was used. Example 17
To 32 and Comparative Examples 4 to 6, the electrical characteristics test (I) was performed to evaluate the electrical characteristics of each of the photosensitive members. Table 6 shows the types of the charge generating agent, the hole transporting agent, and the electron transporting agent used in each of the examples and the comparative examples, and the test results of the electrical characteristics.

[0219]

[Table 6]

Examples 33 to 36 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was produced in the same manner as in Examples 1 to 4, except that G2-2) was used. Examples 37 to 40 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 5 to 8, except that G2-2) was used.

Examples 41 to 44 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 9 to 12, except that G2-2) was used. Examples 45 to 48 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 13 to 16, except that G2-2) was used.

Comparative Examples 7 to 9 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was produced in the same manner as in Comparative Examples 1 to 3, except that G2-2) was used. Example 33
To 48 and Comparative Examples 7 to 9 were subjected to the above-described electrical property test (I) to evaluate the electrical properties of each of the photosensitive bodies. Table 7 shows the types of the charge generating agent, the hole transporting agent, and the electron transporting agent used in each of the examples and comparative examples, and the test results of the electrical characteristics.

[0221]

[Table 7]

(Laminated Photoreceptor for Digital Light Source) Example 49 X-Type Non-Metallic Phthalocyanine (CG1-1) as Charge Generating Agent
2.5 parts by weight and binder resin (polyvinyl butyral)
One part by weight was mixed and dispersed in a ball mill together with 15 parts by weight of a solvent (tetrahydrofuran) to prepare a coating liquid for a charge generation layer. Next, this coating solution was applied on a conductive substrate (aluminum pipe) by dip coating, and
The resultant was dried with hot air at 0 ° C. for 30 minutes to form a charge generation layer having a thickness of 0.5 μm.

Next, a stilbene derivative which is a hole transporting agent
(11-2) 1 part by weight and binder resin (polycarbonate) 1
The parts by weight were mixed and dispersed in a ball mill together with 10 parts by weight of a solvent (tetrahydrofuran) to prepare a coating liquid for a charge transport layer. Next, this coating solution is applied on the charge generation layer by dip coating, and dried with hot air at 110 ° C. for 30 minutes to form a charge generation layer having a thickness of 20 μm. did.

Example 50 A laminated photosensitive member for a digital light source was manufactured in the same manner as in Example 49 except that the stilbene derivative (11-4) was used as the hole transporting agent. Example 51 A laminated photoconductor for a digital light source was produced in the same manner as in Example 49 except that the stilbene derivative (12-4) was used as the hole transporting agent.

Example 52 A laminated photoreceptor for a digital light source was manufactured in the same manner as in Example 49 except that the stilbene derivative (11-8) was used as the hole transporting agent. Examples 53 to 56 α-oxotitanyl phthalocyanine (C
A laminated photoreceptor for a digital light source was manufactured in the same manner as in Examples 49 to 52 except that G2-1) was used.

Examples 57 to 60 Y-type oxotitanyl phthalocyanine (C
A laminated photoreceptor for a digital light source was manufactured in the same manner as in Examples 49 to 52 except that G2-2) was used. Comparative Examples 10 to 12 Laminated photoconductors for digital light sources were manufactured in the same manner as in Examples 49, 53 and 57, except that the stilbene derivative (2-1) was used as the hole transporting agent.

Examples 49 to 60 and Comparative Examples 10 to
The following electrical characteristics test (II) was performed on the photoreceptor obtained in Step 12.
And evaluated the electrical characteristics of each photoconductor. Electrical characteristics test (II) Except that the surface of the photoreceptor was charged to -700 ± 20V,
The surface potential V was determined in the same manner as in the electrical characteristic test (I).
_o (V), residual potential V _r (V) and half-exposure amount E _1/2
(ΜJ / cm ² ) was determined.

Table 8 shows the types of the charge generating agent and the hole transporting agent used in the above Examples and Comparative Examples, and the test results of the electrical characteristics.

[0229]

[Table 8]

(Single-layer type photoreceptor for analog light source) Examples 61 to 64 As a charge generating agent, the following formula (CG3-1)

[0231]

Embedded image

Except that the perylene pigment represented by
A single-layer photoreceptor for an analog light source was manufactured in the same manner as in Examples 1 to 4. Examples 65 to 68 Single layer photoconductors for analog light sources were manufactured in the same manner as in Examples 5 to 8, except that perylene pigment (CG3-1) was used as the charge generator.

Examples 69 to 72 Single-layer photoconductors for analog light sources were produced in the same manner as in Examples 9 to 12, except that perylene pigment (CG3-1) was used as the charge generator. Examples 73 to 76 Single-layer photoconductors for analog light sources were manufactured in the same manner as in Examples 13 to 16, except that perylene pigment (CG3-1) was used as the charge generator.

Comparative Examples 13 to 15 Single-layer type photoreceptors for analog light sources were produced in the same manner as in Comparative Examples 1 to 3, except that perylene pigment (CG3-1) was used as the charge generator. The photoconductors obtained in Examples 61 to 76 and Comparative Examples 13 to 15 were subjected to the following electrical property test (III) to evaluate the electrical properties of each photoconductor.

Electric property test (III) The surface potential V _o (V) and residual electric potential were _{measured in the same} manner as in the electric property test (I), except that white light (light intensity of 8 lux) of a halogen lamp was used as an exposure light source. The potential V _r (V) and the half-life exposure amount E _1/2 (lux · sec) were determined. Table 9 shows the types of the charge generating agent, the hole transporting agent, and the electron transporting agent used in the above Examples and Comparative Examples, and the test results of the electrical characteristics.

[0236]

[Table 9]

Examples 77 to 80 The following formula (CG4-1) was used as the charge generating agent:

[0238]

Embedded image

Aside from using the bisazo pigment represented by
A single-layer photosensitive member for an analog light source was manufactured in the same manner as in Examples 61 to 64. Examples 81 to 84 Single-layer photoconductors for analog light sources were produced in the same manner as in Examples 65 to 68 except that bisazo pigment (CG4-1) was used as the charge generator.

Examples 85 to 88 Single-layer photoreceptors for analog light sources were produced in the same manner as in Examples 69 to 72 except that bisazo pigment (CG4-1) was used as the charge generator. Examples 89 to 92 Single layer photoconductors for analog light sources were manufactured in the same manner as in Examples 73 to 76 except that bisazo pigment (CG4-1) was used as the charge generator.

Comparative Examples 16 to 18 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Comparative Examples 13 to 15, except that bisazo pigment (CG4-1) was used as the charge generator. The photoconductors obtained in Examples 77 to 92 and Comparative Examples 16 to 18 were subjected to the electric property test (III) to evaluate the electric characteristics of each photoconductor. Table 10 shows the types of the charge generating agent, the hole transporting agent, and the electron transporting agent used in each of the examples and comparative examples, and the test results of the electrical characteristics.

[0242]

[Table 10]

Examples 93 to 96 As a charge generator, a compound represented by the formula (CG4-2):

[0244]

Embedded image

Aside from using the bisazo pigment represented by the following formula,
A single-layer photosensitive member for an analog light source was manufactured in the same manner as in Examples 61 to 64. Examples 97 to 100 Single layer photoconductors for analog light sources were produced in the same manner as in Examples 65 to 68 except that bisazo pigment (CG4-2) was used as the charge generator.

Examples 101 to 104 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Examples 69 to 72 except that bisazo pigment (CG4-2) was used as a charge generator. Examples 105 to 108 A single-layer photoreceptor for an analog light source was manufactured in the same manner as in Examples 73 to 76 except that a bisazo pigment (CG4-2) was used as a charge generator.

Comparative Examples 19 to 21 Single-layer photosensitive members for analog light sources were produced in the same manner as in Comparative Examples 13 to 15, except that bisazo pigment (CG4-2) was used as the charge generator. The photoconductors obtained in Examples 93 to 108 and Comparative Examples 19 to 21 were subjected to the electric property test (III) to evaluate the electric characteristics of each photoconductor.
Table 11 shows the types of the charge generating agent, the hole transporting agent and the electron transporting agent used in each of the examples and the comparative examples, and the test results of the electrical characteristics.

[0248]

[Table 11]

Examples 109 to 112 As a charge generator, a compound represented by the formula (CG4-3):

[0250]

Embedded image

[0251] Except for using the bisazo pigment represented by
A single-layer photosensitive member for an analog light source was manufactured in the same manner as in Examples 61 to 64. Examples 113 to 116 Single layer photoconductors for analog light sources were manufactured in the same manner as in Examples 65 to 68 except that bisazo pigment (CG4-3) was used as the charge generator.

Examples 117 to 120 Single-layer photoreceptors for analog light sources were produced in the same manner as in Examples 69 to 72 except that bisazo pigment (CG4-3) was used as the charge generator. Examples 121 to 124 Single layer photoconductors for analog light sources were manufactured in the same manner as in Examples 73 to 76 except that bisazo pigment (CG4-3) was used as the charge generator.

Comparative Examples 22 to 24 Single-layer photosensitive members for analog light sources were produced in the same manner as in Comparative Examples 13 to 15, except that bisazo pigment (CG4-3) was used as the charge generator. The photoconductors obtained in Examples 109 to 124 and Comparative Examples 22 to 24 were subjected to the electric property test (III) to evaluate the electric characteristics of each photoconductor. Table 12 shows the types of the charge generating agent, the hole transporting agent, and the electron transporting agent used in each of the examples and comparative examples, and the test results of the electrical characteristics.

[0254]

[Table 12]

(Laminated photoconductor for analog light source) Examples 125 to 128 The laminated photoconductor for analog light source was prepared in the same manner as in Examples 49 to 52 except that perylene pigment (CG3-1) was used as the charge generating agent. Body manufactured. Examples 129 to 132 Laminated photoconductors for analog light sources were manufactured in the same manner as in Examples 49 to 52 except that bisazo pigment (CG4-1) was used as the charge generator.

Examples 133 to 136 Except that a bisazo pigment (CG4-2) was used as a charge generating agent, laminated photoreceptors for analog light sources were manufactured in the same manner as in Examples 49 to 52. Examples 137 to 140 Laminated photoconductors for analog light sources were manufactured in the same manner as in Examples 49 to 52 except that bisazo pigment (CG4-3) was used as the charge generator.

Comparative Examples 25 to 28 Except that the stilbene derivative (2-1) was used as the hole transporting agent, a laminated photoreceptor for an analog light source was produced in the same manner as in Examples 125, 129, 133 and 137. . The photoconductors obtained in Examples 125 to 140 and Comparative Examples 25 to 28 were subjected to the following electric property test (IV) to evaluate the electric characteristics of each photoconductor.

Electrical Characteristics Test (IV) Except that the surface of the photoreceptor was charged to -700 ± 20 V,
The surface potential V was determined in the same manner as in the electrical property test (III).
_o (V), residual potential V _r (V) and half decay exposure amount E _1/2
(Lux · second). Table 13 shows the types of the charge generating agent and the hole transporting agent used in the above Examples and Comparative Examples, and the test results of the electrical characteristics.

[0259]

[Table 13]

Example 141 A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Example 1, except that the stilbene derivative represented by 21-1 in Table 3 was used as the hole transporting agent. . Example 142 A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Example 1, except that the stilbene derivative represented by 22-1 in Table 3 was used as the hole transporting agent.

Example 143 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 1, except that the stilbene derivative represented by 21-3 in Table 3 was used as the hole transporting agent. . Example 144 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 1, except that the stilbene derivative represented by 22-4 in Table 3 was used as the hole transporting agent.

Example 145 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 5, except that the stilbene derivative represented by 21-1 in Table 3 was used as the hole transporting agent. . Example 146 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 5, except that the stilbene derivative represented by 22-1 in Table 3 was used as the hole transporting agent.

Example 147 A single-layer photosensitive member for a digital light source was manufactured in the same manner as in Example 5, except that the stilbene derivative represented by 21-3 in Table 3 was used as the hole transporting agent. . Example 148 A single-layer photoreceptor for a digital light source was produced in the same manner as in Example 5, except that the stilbene derivative represented by 22-4 in Table 3 was used as the hole transporting agent.

Examples 149 to 152 Single-layer photosensitive members for digital light sources were produced in the same manner as in Examples 145 to 148, except that the naphthoquinone derivative (ET14-1) was used as the electron transporting agent. Examples 153 to 156 Single-layer photoreceptors for digital light sources were produced in the same manner as in Examples 145 to 148 except that a naphthoquinone derivative (ET14-2) was used as an electron transporting agent.

The photosensitive members obtained in Examples 141 to 156 were subjected to the electrical property test (I) to evaluate the electrical properties of each photosensitive member. Table 14 shows the types of the charge generating agent, the hole transporting agent and the electron transporting agent used in each example, and the test results of the electrical characteristics.

[0266]

[Table 14]

Examples 157 to 160 As a charge generating agent, α-oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 141 to 144 except that G2-1) was used. Examples 161 to 164 α-oxotitanyl phthalocyanine (C
A single-layer type photoreceptor for a digital light source was manufactured in the same manner as in Examples 145 to 148 except that G2-1) was used.

Examples 165 to 168 α-oxotitanyl phthalocyanine (C
A single-layer type photoreceptor for a digital light source was manufactured in the same manner as in Examples 149 to 152 except that G2-1) was used. Examples 169 to 172 α-oxotitanyl phthalocyanine (C
A single-layer type photoreceptor for a digital light source was manufactured in the same manner as in Examples 153 to 156, except that G2-1) was used.

The photosensitive members obtained in Examples 157 to 172 were subjected to the above-mentioned electrical property test (I) to evaluate the electrical properties of each photosensitive member. Table 15 shows the types of the charge generating agent, the hole transporting agent and the electron transporting agent used in each example, and the test results of the electrical characteristics.

[0270]

[Table 15]

Examples 173 to 176 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was produced in the same manner as in Examples 141 to 144 except that G2-2) was used. Examples 177 to 180 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 145 to 148, except that G2-2) was used.

Examples 181-184 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was manufactured in the same manner as in Examples 149 to 152 except that G2-2) was used. Examples 185 to 188 Y-type oxotitanyl phthalocyanine (C
A single-layer photoreceptor for a digital light source was produced in the same manner as in Examples 153 to 156, except that G2-2) was used.

The photosensitive members obtained in Examples 173 to 188 were subjected to the electrical property test (I) to evaluate the electrical properties of each photosensitive member. Table 16 shows the types of the charge generating agent, the hole transporting agent and the electron transporting agent used in each example, and the test results of the electrical characteristics.

[0274]

[Table 16]

(Laminated photoreceptor for digital light source) Example 189 A laminated photoreceptor for digital light source was manufactured in the same manner as in Example 49 except that the stilbene derivative (21-1) was used as the hole transporting agent. did. Example 190 A laminated photoconductor for a digital light source was produced in the same manner as in Example 49 except that the stilbene derivative (22-1) was used as the hole transporting agent.

Example 191 A laminated photoreceptor for a digital light source was manufactured in the same manner as in Example 49 except that the stilbene derivative (21-3) was used as the hole transporting agent. Example 192 A laminated photoconductor for a digital light source was manufactured in the same manner as in Example 49 except that the stilbene derivative (22-4) was used as the hole transporting agent.

Examples 193 to 196 α-oxotitanyl phthalocyanine (C
A laminated photoreceptor for a digital light source was manufactured in the same manner as in Examples 189 to 192 except that G2-1) was used. Examples 197 to 200 Y-type oxotitanyl phthalocyanine (C
A laminated photoreceptor for a digital light source was manufactured in the same manner as in Examples 189 to 192 except that G2-2) was used.

The photosensitive members obtained in Examples 189 to 200 were subjected to the above-mentioned electrical property test (II) to evaluate the electrical properties of each photosensitive member. Table 17 shows the types of the charge generating agent and the hole transporting agent used in each example, and the test results of the electrical characteristics.
Shown in

[0279]

[Table 17]

(Single-layer type photoreceptor for analog light source) Examples 201 to 204 Single layers for analog light source were prepared in the same manner as in Examples 141 to 144 except that perylene pigment (CG3-1) was used as a charge generating agent. A photoreceptor was manufactured. Examples 205 to 208 Single-layer photoconductors for analog light sources were manufactured in the same manner as in Examples 145 to 148 except that perylene pigment (CG3-1) was used as the charge generator.

Examples 209 to 212 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Examples 149 to 152 except that perylene pigment (CG3-1) was used as the charge generating agent. Examples 213 to 216 Single-layer photoconductors for analog light sources were produced in the same manner as in Examples 153 to 156, except that perylene pigment (CG3-1) was used as the charge generator.

The photosensitive members obtained in Examples 201 to 216 were subjected to the electrical property test (III) to evaluate the electrical properties of each photosensitive member. Charge generating agent used in each example,
Table 18 shows the types of the hole transporting agent and the electron transporting agent, and the test results of the electrical characteristics.

[0283]

[Table 18]

Examples 217 to 220 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Examples 201 to 204 except that bisazo pigment (CG4-1) was used as the charge generator. Examples 221 to 224 A single-layer photosensitive member for an analog light source was manufactured in the same manner as in Examples 205 to 208 except that a bisazo pigment (CG4-1) was used as a charge generator.

Examples 225 to 228 Single layer photoconductors for analog light sources were produced in the same manner as in Examples 209 to 212 except that bisazo pigment (CG4-1) was used as the charge generator. Examples 229 to 232 Single-layer photoreceptors for analog light sources were produced in the same manner as in Examples 213 to 216, except that bisazo pigment (CG4-1) was used as the charge generator.

The photosensitive members obtained in Examples 217 to 232 were subjected to the above-described electrical property test (III), and the electrical properties of each photosensitive member were evaluated. Charge generating agent used in each example,
Table 19 shows the types of the hole transporting agent and the electron transporting agent, and the test results of the electrical characteristics.

[0287]

[Table 19]

Examples 233 to 236 Single-layer photoreceptors for analog light sources were manufactured in the same manner as in Examples 201 to 204 except that bisazo pigment (CG4-2) was used as the charge generator. Examples 237 to 240 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Examples 205 to 208 except that bisazo pigment (CG4-2) was used as the charge generator.

Examples 241 to 244 Single layer photoconductors for analog light sources were manufactured in the same manner as in Examples 209 to 212 except that bisazo pigment (CG4-2) was used as the charge generator. Examples 245 to 248 A single-layer photoreceptor for an analog light source was produced in the same manner as in Examples 213 to 216, except that a bisazo pigment (CG4-2) was used as the charge generator.

The photosensitive members obtained in Examples 233 to 248 were subjected to the above-mentioned electrical property test (III) to evaluate the electrical properties of each photosensitive member. Charge generating agent used in each example,
Table 20 shows the types of the hole transporting agent and the electron transporting agent, and the test results of the electrical characteristics.

[0291]

[Table 20]

Examples 249 to 252 Single-layer photosensitive members for analog light sources were produced in the same manner as in Examples 201 to 204 except that bisazo pigment (CG4-3) was used as the charge generator. Examples 253 to 256 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Examples 205 to 208 except that bisazo pigment (CG4-3) was used as the charge generator.

Examples 257 to 260 Single-layer photosensitive members for analog light sources were manufactured in the same manner as in Examples 209 to 212 except that bisazo pigment (CG4-3) was used as the charge generator. Examples 261 to 264 Single-layer photoconductors for analog light sources were manufactured in the same manner as in Examples 213 to 216, except that bisazo pigment (CG4-3) was used as the charge generator.

The photosensitive members obtained in Examples 249 to 264 were subjected to the above-mentioned electrical property test (III) to evaluate the electrical properties of each photosensitive member. Charge generating agent used in each example,
Table 21 shows the types of the hole transporting agent and the electron transporting agent, and the test results of the electrical characteristics.

[0295]

[Table 21]

(Laminated photoconductor for analog light source) Examples 265 to 268 Laminated photoconductor for analog light source was performed in the same manner as in Examples 189 to 192 except that perylene pigment (CG3-1) was used as a charge generating agent. Body manufactured. Examples 269 to 272 Laminated photoconductors for analog light sources were manufactured in the same manner as in Examples 189 to 192 except that bisazo pigment (CG4-1) was used as the charge generator.

Examples 273 to 276 Except that a bisazo pigment (CG4-2) was used as a charge generating agent, a laminated photoreceptor for an analog light source was manufactured in the same manner as in Examples 189 to 192. Examples 277 to 280 Laminated photoconductors for analog light sources were manufactured in the same manner as in Examples 189 to 192, except that bisazo pigment (CG4-3) was used as the charge generator.

The photosensitive members obtained in Examples 265 to 280 were subjected to the following electrical property test (IV) to evaluate the electrical properties of each photosensitive member. Table 2 shows the types of the charge generating agent and the hole transporting agent used in each example, and the test results of the electrical characteristics.
It is shown in FIG.

[0299]

[Table 22]

As apparent from Tables 5 to 22, Example 1
The electrophotographic photosensitive member 280 has a small absolute value of the residual potential V _r as compared with the comparative examples corresponding to the embodiments. Also, the half-life exposure amount E _1/2 is equal to or less than the value in the corresponding comparative example. From this, the first embodiment
It can be seen that the electrophotographic photoreceptors No. to 280 have excellent sensitivity.

[0301]

As described in detail above, the stilbene derivatives (1) and (2) of the present invention have high compatibility with the binder resin and high charge transport ability (hole transport ability). Further, the electrophotographic photoreceptor of the present invention is characterized in that the stilbene derivative is
Since (1) and (2) are used as hole transport agents, the sensitivity is high. Therefore, the electrophotographic photoreceptor of the present invention has a specific function and effect that contributes to speeding up and improving performance of various image forming apparatuses such as an electrostatic copying machine and a laser beam printer.

[Brief description of the drawings]

FIG. 1 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (11-4).

FIG. 2 is a graph showing an infrared absorption spectrum of a stilbene derivative (11-4).

FIG. 3 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (12-4).

FIG. 4 is a graph showing an infrared absorption spectrum of a stilbene derivative (12-4).

FIG. 5 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (11-8).

FIG. 6 is a graph showing an infrared absorption spectrum of a stilbene derivative (11-8).

FIG. 7 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (12-8).

FIG. 8 is a graph showing an infrared absorption spectrum of a stilbene derivative (12-8).

FIG. 9 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (11-2).

FIG. 10 is a graph showing an infrared absorption spectrum of a stilbene derivative (11-2).

FIG. 11 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (11-5).

FIG. 12 is a graph showing an infrared absorption spectrum of a stilbene derivative (11-5).

FIG. 13 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (11-15).

FIG. 14 is a graph showing an infrared absorption spectrum of a stilbene derivative (11-15).

FIG. 15 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (11-3).

FIG. 16 is a graph showing an infrared absorption spectrum of a stilbene derivative (11-3).

FIG. 17 is a graph showing a ¹ H-NMR spectrum of a stilbene derivative (21-1).

FIG. 18 is a graph showing an infrared absorption spectrum of a stilbene derivative (21-1).

Claims (4)

[Claims] [Claim 1] General formula (1):(Where R¹And R^ThreeAre the same or different alkyl
A group represented by R^TwoAnd R ^FourAre the same or different, and
Indicates an atom or an alkyl group. )
A stilbene derivative. (2) The general formula (2):(Where R^Five, R⁶, R⁷, R⁸, R⁹, R^Ten, R¹¹,
R¹², R¹³And R¹⁴Are the same or different and are a hydrogen atom
Or an alkyl group. Where R^Five, R⁶, R ⁷, R
⁸And R⁹At least three of them represent an alkyl group
Then R^Ten, R¹¹, R ¹², R¹³And R¹⁴At least
Also three represent an alkyl group. )
Stilbene derivatives. 3. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive substrate, wherein the photosensitive layer is a compound represented by the general formula:
An electrophotographic photoreceptor comprising at least one stilbene derivative represented by (1) and the general formula (2) according to claim 2. 4. The general formula (1) according to claim 1, wherein said photosensitive layer is
And a single-layer photosensitive layer containing a charge generating agent and an electron transporting agent in addition to at least one stilbene derivative represented by the general formula (2) according to claim 2. Photoreceptor.