JP2873745B2 - Bisstyryl compound and electrophotographic photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a bisstyryl compound and an electrophotographic photosensitive member, and more particularly to a bisstyryl compound suitable as the carrier transporting material in an electrophotographic photosensitive member having a photosensitive layer containing a carrier generating substance and a carrier transporting substance. And an electrophotographic photosensitive member.

[0002]

2. Description of the Related Art Conventionally, selenium,
Photoconductors containing an inorganic photoconductor such as zinc oxide, cadmium sulfide, or silicon as a main component have been widely known. However, these materials are not always satisfactory in characteristics such as thermal stability and durability, and have problems in production and handling.

On the other hand, a photoreceptor having a photosensitive layer containing an organic photoconductive compound as a main component is relatively easy to manufacture, inexpensive, easy to handle, and generally used as a selenium photoreceptor. Excellent heat stability. As such an organic photoconductor compound, poly-N-vinylcarbazole is well known, and this is combined with 2,4,7-
A photoreceptor having a photosensitive layer containing a charge transfer complex formed from a Lewis acid such as trinitro-9-fluorenone as a main component has already been put to practical use.

On the other hand, there is known a photoreceptor having a function-separated type photosensitive layer of a laminated type or a single layer type in which a carrier generating function and a carrier transporting function of a photoconductor are respectively assigned to different substances. For example, a photoreceptor having a photosensitive layer composed of a carrier generating layer composed of a thin amorphous selenium layer and a carrier transporting layer containing poly-N-vinylcarbazole as a main component has already been put to practical use.

[0005] However, poly-N-vinylcarbazole lacks flexibility, and its film is hard and brittle, easily cracks and peels off, and the photoreceptor using it has poor durability. Therefore, if this disadvantage is improved by adding a plasticizer, the residual potential increases in the electrophotographic process, and the residual potential accumulates with repeated use, so that the fog gradually increases and the copied image is damaged.

[0006] In addition, since low molecular organic photoconductive compounds generally do not have a film-forming ability, they are used in combination with an appropriate binder, and by selecting the kind and composition ratio of the binder, the physical properties or photosensitive properties of the film are determined. However, the types of organic photoconductive compounds having high compatibility with the binder are limited. Actually, there are few types of binders that can be used for forming the photosensitive layer of the electrophotographic photosensitive member.

[0007] For example, 2,5-bis (p-diethylaminophenyl) -1,1,2
3,4-Oxadiazole has low compatibility with a binder commonly used as a material of a photosensitive layer of an electrophotographic photosensitive member, for example, polyester and polycarbonate. That is,
When the photosensitive layer is formed by mixing at the required ratio to adjust the electrophotographic properties, oxadiazole crystals will precipitate at a temperature of 50 ° C or higher, and the electrophotographic properties such as charge retention and sensitivity will decrease. Have the disadvantage of

On the other hand, the diarylalkane derivative described in US Pat. No. 3,820,989 has little compatibility problem with the binder, but has low stability to light, and is obtained by repeating transfer electrophotography in which charging and exposure are repeatedly performed. When used for the photoreceptor, there is a disadvantage that the sensitivity of the photosensitive layer gradually decreases.

No. 3,274,000, US Pat.
No. 36428 describes different types of phenothiazine derivatives, but all have the disadvantages of low photosensitivity and low stability upon repeated use.

Also, Japanese Patent Application Laid-Open Nos. 58-65440 and 58-190953
The stilbene compounds described in JP-A Nos. 63-149652 are relatively good in charge retention and sensitivity, but are not satisfactory in durability upon repeated use.

On the other hand, Japanese Patent Application Laid-Open Nos.
Nos. 174749, 62-120346, 64-32265, JP-A-1
A photoconductor using a distilbene compound as a carrier transporting material, such as -1006069, 1-93746, and 1-274154, is a photoconductor that substantially solves the above-mentioned disadvantages, but is used in copiers and printers. It is not satisfactory in durability when incorporated and used repeatedly.

In particular, the following four points have become problems. 1) In a high-speed copying machine with a high linear velocity, the cycle of charging, exposing, and discharging is shortened, so that the residual potential greatly increases during repeated copying.

2) In the case of a copying machine, small white dot-like image defects (referred to as white spots) are generated in solid black portions when copying is repeated.

3) In the case of a reversal developing printer, defects have been found in which the exposure potential (VL) increases at low temperatures and the charging potential (VH) decreases with repeated use.

4) Small black dot-like image defects (referred to as black spots) are likely to occur in the white portion.

As described above, at present, a carrier transporting material having practically satisfactory characteristics for producing an electrophotographic photosensitive member has not yet been found.

[0017]

SUMMARY OF THE INVENTION An object of the present invention is to provide a compound and an electrophotographic photoreceptor suitable as a carrier transporting substance for a highly sensitive and highly durable photoreceptor which can be used in a copying machine, a printer and the like.

Further, other objects of the present invention are as follows (1) to (4).

(1) In a high-speed copying machine with a high linear speed,
Provided are a compound suitable as a carrier transporting material for a photoreceptor and an electrophotographic photoreceptor which do not increase in residual potential even after repeated charging, exposing and discharging.

(2) A compound suitable as a carrier transporting material for a photoreceptor which does not generate small white dot-like image defects (referred to as white spots) in solid black areas when used repeatedly in a copying machine. And an electrophotographic photoreceptor.

(3) When used in a reversal developing printer, the exposure potential (V
L) does not rise, and the charging potential (VH) after repeated use
To provide a compound and an electrophotographic photoreceptor suitable as a carrier-generating substance for a photoreceptor which does not decrease the photoreceptor.

(4) To provide a compound and an electrophotographic photoreceptor suitable as a carrier transporting material for a photoreceptor which do not generate small black dot-like image defects (referred to as black spots) in a white portion.

[0023]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention relates to a bisstyryl compound represented by the following general formula [I] or [II] and an electrophotographic photoreceptor containing this bisstyryl compound.

Embedded image [However, n = 0 or n> 1. When n = 0, R ¹
Is a chlorine atom or a cyano group substituted at the 2- or 3-position with respect to the substituted amino group, or a fluorine atom, a bromine atom, an iodine atom or a halogenated alkyl group substituted at the 2- to 4-position And when n> 1, R
¹ is a halogen atom, a cyano group or a halogenated alkyl group having 1 to 4 carbon atoms, which is substituted at 2- to 4-position to the substituted amino group. R ² may be different from each other, and may be a halogen atom, a cyano group, or a group having 1 to 4 carbon atoms.
And substituents selected from halogenated alkyl groups having 1 to 4 carbon atoms. Ar ¹ and Ar ² may be different from each other;

Embedded image Is an aryl group represented by ｛However, x ≧ 0, y ≧
0, z ≧ 0, and when x, y, z is 2 or more, a plurality of R ³ , R ⁴ , R ⁵ may be different from each other, and may be a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, A phenyl group, an aralkyl group, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms,

Embedded image (However, R ⁶ and R ⁷ may be different from each other and are an alkyl group or an aralkyl group having 1 to 4 carbon atoms.) And -OR ⁸ (where R ⁸ is a group having 1 to 4 carbon atoms). An alkyl group). ｝)

[0024]

Embedded image [However, n = 0 or n> 1. When n = 0, R ¹¹
Is a methoxy or diethylamino group substituted at the 2- or 3-position with respect to the substituted amino group, or 2- to
An ethoxy group or a dimethylamino group substituted at the 4-position, and when n> 1, R ¹¹ represents a methoxy group, an ethoxy group, or a dimethyl group substituted at the 2- to 4-position with respect to the substituted amino group. It is an amino group or a diethylamino group.
R ¹² may be different from each other, and may be a halogen atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, a methoxy group,
It is a substituent selected from an ethoxy group, a dimethylamino group and a diethylamino group. Ar ³ and Ar ⁴ may be different from each other,

Embedded image Is an aryl group represented by ｛However, x ≧ 0, y ≧
0, z ≧ 0, and when x, y, z is 2 or more, a plurality of R ¹³ , R ¹⁴ , and R ¹⁵ may be different from each other, and may be a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, Group,
An aralkyl group, an alkyl group having 1 to 4 carbon atoms,

Embedded image (However, R ¹⁶ and R ¹⁷ may be different from each other and are an alkyl group or an aralkyl group having 1 to 4 carbon atoms.), -OR ¹⁸ (where R ¹⁸ is a group having 1 to 4 carbon atoms) An alkyl group), -R ¹⁹ COOR ²⁰ (where R ¹⁹ is an alkylene group having 1 to 4 carbon atoms and R ²⁰ is an alkyl group) and a substituent selected from -R ¹⁹ OCOR ²⁰ It is. ｝ However, the following compounds are excluded.

Embedded image (Here, a plurality of R ²¹ and R ²² may be different from each other and are an alkyl group having 1 to 4 carbon atoms. Further, r ≧ 2 and t ≧ 0.)]

The compounds of the above general formulas [I] and [II] of the present invention have the following A to C characteristics and are suitable as carrier transport materials for electrophotographic photoreceptors.

(A). Since it has a substituent in the molecule and a pair of styryl groups is a bisstyryl compound having an asymmetric structure, sensitivity and durability are improved, and fluctuations in charging potential are reduced. When used repeatedly, a good image free from image defects and image defects such as white spots, black spots, fog, and reduced density can be obtained.

(B). In addition, when incorporated in a high-speed copying machine or printer and used repeatedly, the residual potential is reduced, so that a good image free from image defects and image defects can be obtained. (C). Since it is a bisstyryl compound, synthesis is easy.

Specific compound No. of the above general formula [I]
<1> to <189> are collectively illustrated in the following description.

Next, a synthesis example of the compound of the general formula [I] will be described. The outline of the synthesis formula is shown below.

(Synthesis Example 1: Synthesis of Exemplified Compound <23>) The diformyl compound 3 was synthesized as follows according to a known method. 2-Fluoro-6-methylaniline 1 (manufactured by Tokyo Chemical Industry) (1 mole ratio) and iodobenzene (manufactured by Tokyo Chemical Industry)
(2.5 mole ratio), potassium carbonate (Kanto Chemical Co., Ltd.) (2 mole ratio) and copper powder (Kanto Chemical Co., Ltd.) (0.2 mole ratio)
Reaction was carried out at an internal temperature of 190 to 210 ° C. for 50 hours, and after the post-treatment, the column was purified to give 2-fluoro-6-methyltriphenylamine.
2 was obtained in a yield of 60% (Ullman reaction).

N, N-dimethylformamide (manufactured by Kanto Kagaku) (4 mole ratio) and phosphorus oxychloride (manufactured by Wako Pure Chemical Industries, Ltd.) are added to 2-fluoro-6-methyltriphenylamine 2 (1 mole ratio). 3 mol ratio), and 24 at an internal temperature of 70 to 90 ° C.
After reacting for an hour, post-treatment and column purification, N, N-bis (4-formyl-phenyl) -2-fluoro-6-methylaniline 3 was obtained at a yield of 55% (Vilsmeier reaction).

The synthesis of the diethyl phosphonate was carried out according to a known method as follows. Benzophenone (Tokyo Kasei) in methanol (Kanto Chemical) (1 mole ratio)
Was added, and sodium borohydride (manufactured by Kanto Chemical Co., Ltd.) (0.5 mol ratio) was added. The mixture was reacted at an internal temperature of 10 to 20 ° C. for 5 hours. After work-up, the column was purified to obtain a hydroxy compound in 92% yield. (Reduction reaction).

The hydroxy compound (1 mole ratio) was put in toluene (manufactured by Wako Pure Chemical Industries, Ltd.), and thionyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.2 mole ratio) was added.
After the reaction, the chlorinated product was obtained in a yield of 93% after the post-treatment (substitution reaction).

Triethyl phosphite (manufactured by Kanto Chemical Co., Ltd.) (1.2 mole ratio) was added to the chlorinated product (1 mole ratio), and the internal temperature was 140 ° C.
The mixture was reacted at -160 ° C for 10 hours, and purified by distillation after the post-treatment to obtain a diethyl phosphonate in a yield of 90% (diethyl phosphonate reaction).

The synthesis of CTM was carried out as follows using the compound obtained as described above as a raw material. 12.2 g (0.033 mol) of N, N-bis (4-formyl-phenyl) -2-fluoro-6-methylaniline and 20 g (0.066 mol) of diethyl 1,1-diphenylmethylphosphonate were added to toluene (Wako Pure Chemical Industries, Ltd.). Dissolved in 50 ml). Sodium methoxide (manufactured by Kanto Chemical Co.) 3.6 g (0.066 mol)
Was added to 50 ml of toluene, and the solution was added to the above solution under ice cooling while keeping the internal temperature at 25 ° C. or lower. Then at room temperature
Stirred for hours. Add 100 ml of water, wash the toluene layer with water,
Then, water was removed from the toluene layer with sodium sulfate (manufactured by Kanto Chemical Co., Ltd.), the solvent was distilled off, and the obtained residue was purified by a silica column to yield the desired Exemplified Compound <23> as a yellow-white crystal. 14.3 g (0.023 mol) was obtained at 70%.

The melting point was 123-125 ° C. Elemental analysis values were as follows. IR data of exemplary compound <23> (the spectrum is shown in FIG. 1). 1595cm ^-, S (Strong: hereinafter the same)

(Synthesis Example 2. Synthesis of Exemplified Compound <32>) In Synthesis Example 1, 2-fluoro-6-methylaniline was converted to 3,4
-Synthesized in the same manner as in Synthesis Example 1 except that dichloroaniline was used, and the exemplified compound was converted into yellowish white crystals in a yield of 70%.
15.4 g (0.023 mol) were obtained.

The melting point was 118-124 ° C. Elemental analysis was as follows.

(Synthesis Example 3. Synthesis of Exemplified Compound <67>) Synthesis was performed in the same manner as in Synthesis Example 1 except that benzophenone was changed to 4-methylbenzophenone in Synthesis Example 1, and the exemplified compound was converted to a yellow-white crystal. 12 g (0.018 mol) in 55% yield
Obtained.

The melting point was 106-111 ° C. Elemental analysis was as follows.

(Synthesis Example 4. Synthesis of Exemplified Compound <61>) In Synthesis Example 1, 2-fluoro-6-methylaniline was replaced with 2-chloro-4-methylaniline, and benzophenone was replaced with 4-chloro-4-methylaniline.
-Synthesis was performed in the same manner as in Synthesis Example 1 except that -methylbenzophenone was used.
%, 11.6 g (0.017 mol) was obtained.

The melting point was 117-122 ° C. Elemental analysis was as follows.

(Synthesis Example 5. Synthesis of Exemplified Compound <47>) Synthesis Example 1 was repeated except that 2-fluoro-6-methylaniline was replaced with 4-bromoaniline and benzophenone was replaced with 4-methylbenzophenone. The compound was synthesized in the same manner as in Example 1.
g (0.018 mol) were obtained.

The melting point was 119-125 ° C. Elemental analysis was as follows.

Next, the specific compound N of the above general formula [II]
o. (1) to (319) are collectively illustrated in the following description.

Next, a synthesis example of the compound of the general formula [II] will be described. A schematic diagram of the synthesis formula is shown below.

(Synthesis Example 6: Synthesis of Exemplified Compound (24)) The formyl compound was synthesized according to a known method as follows.
5-chloro-2-methoxyaniline (manufactured by Aldrich)
(1 mole ratio) and iodobenzene (Tokyo Kasei) (2.5
Molar ratio) to potassium carbonate (Kanto Chemical Co., Ltd.) (2 molar ratio)
And copper powder (Kanto Chemical Co., Ltd.) (0.2 molar ratio)
The reaction was carried out at 0 to 210 ° C. for 50 hours, followed by post-treatment and column purification to obtain 5-chloro-2-methoxytriphenylamine in a yield of 55% (Ullman reaction).

N, N-dimethylformamide (manufactured by Kanto Kagaku) (4 mole ratio) and phosphorus oxychloride (manufactured by Wako Pure Chemical Industries) (3 mole ratio) were added to 5-chloro-2-methoxytriphenylaniline (1 mole ratio). Mole ratio) and add 24 at an internal temperature of 70-90 ° C.
After reacting for an hour, post-treatment and column purification, N, N-bis (4-formyl-phenyl) -5-chloro-2-methoxyaniline was obtained in a yield of 45% (Vilsmeier reaction).

The synthesis of the diethyl phosphonate was carried out according to a known method as follows. Benzophenone (Tokyo Kasei) in methanol (Kanto Chemical) (1 mole ratio)
Was added, and sodium borohydride (manufactured by Kanto Chemical Co., Ltd.) (0.5 mol ratio) was added. The mixture was reacted at an internal temperature of 10 to 20 ° C. for 5 hours. After work-up, column purification was performed to obtain a hydroxy compound in a yield of 90%. (Reduction reaction).

The hydroxy compound (1 mole ratio) was put in toluene (manufactured by Wako Pure Chemical Industries, Ltd.), and thionyl chloride (manufactured by Tokyo Chemical Industry) (1.2 mole ratio) was added.
After the reaction, the chlorinated product was obtained in a yield of 94% (substitution reaction).

Triethyl phosphite (manufactured by Kanto Chemical Co., Ltd.) (1.2 mole ratio) was added to the chlorinated body (1 mole ratio), and the internal temperature was 140 ° C.
The reaction was carried out at -160 ° C for 10 hours, followed by post-treatment and purification by distillation to obtain a diethyl phosphonate in 91% yield (diethyl phosphonate reaction).

The synthesis of CTM was carried out as follows using the compound obtained as described above as a raw material. 12 g (0.033 mol) of N, N-bis (4-formyl-phenyl) -5chloro-2-methoxyaniline and 20 g (0.066 mol) of diethyl 1,1-diphenylmethylphosphonate were added to toluene (manufactured by Wako Pure Chemical Industries, Ltd.). ) Dissolved in 50 ml. 3.6 g (0.066 mol) of sodium methoxide (manufactured by Kanto Kagaku Co., Ltd.) was added to 50 ml of toluene, and this solution was added to the above solution under ice-cooling while maintaining the internal temperature at 25 ° C. or lower. Thereafter, the mixture was stirred at room temperature for 3 hours. 100 ml of water was added, the toluene layer was washed with water, then the water was removed from the toluene layer with sodium sulfate (manufactured by Kanto Chemical Co., Ltd.), the solvent was distilled off, and the obtained residue was purified by a silica column to give the desired example. 14.3 g (0.021 mol) of compound (24) was obtained as yellowish white crystals in a yield of 65%.

The melting point was 110-115 ° C. Elemental analysis values were as follows. IR data of exemplary compound (24) (the spectrum is shown in FIG. 2). 1950cm ^-1 , S

(Synthesis Example 7. Synthesis of Exemplified Compound (21)) Synthesis was performed in the same manner as in Synthesis Example 6 except that 5-chloro-2-methoxyaniline was replaced with 3-methoxyaniline. 12.5 g of the exemplified compound as yellowish white crystals in a yield of 60%
(0.0197 mol) obtained.

The melting point was 110-115 ° C. Elemental analysis was as follows.

Synthesis Example 8 Synthesis of Exemplified Compound (206) In Synthesis Example 6, 5-chloro-2-methoxyaniline was converted to 2,4
Synthesis was performed in the same manner as in Synthesis Example 6 except that diethyl 1,1-diphenylmethylphosphonate was replaced with diethyl 1-phenyl-1-P-tolylmethylphosphonate in place of -methoxyaniline, and the exemplified compound was converted to yellowish-white crystals. Yield 62
% Was obtained as 14.1 g (0.02 mol).

The melting point was 107-111 ° C. Elemental analysis was as follows.

The electrophotographic photoreceptor containing the compounds of the above general formulas (I) and (II) as a carrier transporting material can take the forms shown in FIGS.

That is, in FIGS. 3 and 4, the conductive support 1
A carrier generating layer 2 mainly composed of a carrier generating substance
And a photosensitive layer 4 composed of a laminate of a carrier transporting layer 3 containing a carrier transporting substance as a main component according to the present invention. As shown in FIGS. 5 and 6, the photosensitive layer 4 may be provided via an intermediate layer 5 provided on the conductive support 1.

As described above, when the photosensitive layer 4 has a two-layer structure, a photosensitive member having excellent electrophotographic characteristics can be obtained.

In the present invention, as shown in FIGS. 7 and 8, a photosensitive layer 4 formed by dispersing a carrier-generating substance in a layer 6 containing a carrier-transporting substance as a main component is provided on the conductive support 1. May be provided directly or via the intermediate layer 5.

In the present invention, a protective layer 7 may be provided as the outermost layer as shown by the imaginary line in FIG.

The compounds of the general formulas [I] and [II] in the present invention have poor coating forming ability by themselves, so that a photosensitive layer is formed by combining various binders.

Any binder can be used here, but it is hydrophobic and has a high dielectric constant.
It is preferable to use an electrically insulating film-forming polymer.

Examples of such a high-molecular polymer include, but are not limited to, the following.

(P-1) Polycarbonate (P-2) Polyester (P-3) Methacrylic resin (P-4) Acrylic resin (P-5) Polyvinyl chloride (P-6) Polyvinylidene chloride (P-7) Polystyrene (P-8) Polyvinyl acetate (P-9) Styrene-butadiene copolymer (P-10) Vinylidene chloride-acrylonitrile copolymer (P-11) Vinyl chloride-vinyl acetate copolymer (P-12) Chloride Vinyl-vinyl acetate-maleic anhydride copolymer (P-13) Silicone resin (P-14) Silicone-alkyd resin (P-15) Phenol formaldehyde resin (P-16) Styrene-alkyd resin (P-17) Poly -N-vinylcarbazole (P-18) polyvinyl butyral (P-19) polyvinyl formal

These binder resins may be used alone or
It can be used as a mixture of more than one species.

CTM usable in combination in the present invention
Although there is no particular limitation, for example, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives, imidazolidine derivatives,
Bisimidazolidine derivatives, styryl compounds, hydrazone compounds, pyrazoline derivatives, amine derivatives, oxazolone derivatives, benzothiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzofuran derivatives,
Acridine derivative, phenazine derivative, aminostilbene derivative, poly-N-vinylcarbazole, poly-1-
Vinylpyrene and poly-9-vinylanthracene.

As the CTM used in the present invention, those which are excellent in the ability to transport holes generated upon light irradiation to the side of the support and which are suitable for combination with the organic pigment described later used in the present invention are preferable. .

The following are examples of the carrier generating substance used in the carrier generating layer of the photosensitive layer according to the present invention.

(1) Azo dyes such as monoazo dyes, bisazo dyes and trisazo dyes (2) Perylene dyes such as perylene anhydride and perylene imide (3) Indigo dyes such as indigo and thioindigo (4) Anthra Polycyclic quinones such as quinone, pyrenequinone and flavanthrone, etc. (5) Quinacridone dye (6) Bisbenzimidazole dye (7) Indathrone dye (8) Squarylium dye (9) Cyanine dye (10 ) Azulenium dyes (11) Triphenylmethane dyes (12) Amorphous silicon (13) Phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine (14) Selenium, selenium-tellurium, selenium-arsenic (15) Cds, CdSe, (16) pyrylium salt dyes, thiapyrylium salt dyes, etc. It is, may be used alone or in combination of two or more.

In the electrophotographic photosensitive member according to the present invention,
As the CGM, an organic pigment such as a fluorenone-based bisazo pigment, a fluorenylidene-based bisazo pigment, or a polycyclic quinone pigment is preferably used. In particular, when a fluorenone-based bisazo pigment, a fluorenylidene-based bisazo pigment, or a polycyclic quinone pigment represented by the following general formula [F ₁ ] is used in the present invention, the effect is significantly improved in terms of sensitivity, durability, image quality, and the like.

[0073] Specific examples of fluorenone compounds bisazo pigment usable in the present invention as hereinafter described (F ₁ -1~F ₁ -24), but is not limited thereto.

The fluorenone-based bisazo pigment represented by the following general formula [F ₁ ] which can be used in the present invention is easily synthesized by a known method, for example, by a method described in Japanese Patent Application No. 62-304862. .

The fluorenylidene-based bisazo pigment which can be used in the present invention is represented by the following general formula [F ₂ ].

[0076] Examples of useful bisazo pigment of the present invention represented by the general formula [F _2], may be, for example, those represented by the below structural formula (F ₂ -1~F ₂ -7) However, this does not limit the bisazo pigments usable in the present invention.

The polycyclic quinone pigments usable in the present invention are represented by the following general formulas [Q ₁ ] to [Q ₃ ].

Specific examples of the polycyclic quinone pigments represented by the following general formulas [Q ₁ ] to [Q ₃ ] which can be used in the present invention are shown below, but are not limited thereto.

[0079] a later street Taking specific examples of compounds of anthanthrone pigment represented by the general formula [Q _1] (Q ₁ -1~Q ₁ -6).

[0080] a later street Taking specific examples of the compound di-benz pyrene quinone pigments represented by the general formula [Q _2] (Q ₂ -1~Q ₂ -5).

[0081] Aru Taking specific examples of compounds of pyranthrone pigments represented by the general formula [Q _3] (Q ₃ -1~Q ₃ -4) and later of the street.

The general formulas [Q ₁ ] to [Q
_The polycyclic quinone pigment represented by ₃ ] can be easily synthesized by a known method.

As the metal-free phthalocyanine-based pigment that can be used in the present invention, all metal-free phthalocyanine having photoconductivity and derivatives thereof can be used.
Type, β type, τ, τ 'type, η, η' type, Χ type, and
The crystal forms and derivatives thereof described in 62-103651 can be used. In particular, it is desirable to use the τ, Χ, K / R-Χ type.

The Χ-type metal-free phthalocyanine is described in US Pat. No. 3,357,989, and the τ-type metal-free phthalocyanine is described in JP-A-58-182639.

As described in Japanese Patent Application Laid-Open No. 62-103651, the K / R-X type has a 7.7, 9.2, 16.8, 17.5, and CuKα, Bragg angle (2θ ± 0.2 degrees) with respect to an X-ray of 1.541 °.
Main peaks at 22.4 and 28.8 degrees, the peak intensity ratio of 16.8 degrees to the peak intensity of 9.2 degrees is 0.8 to 1.0, and the peak intensity ratio of 28.8 degrees to 22.4 degrees is 0.4 or more. It is a phthalocyanine characterized by these.

The oxytitanyl phthalocyanine usable in the present invention is represented by the following general formula [TP].

As the compounds usable in the present invention, those having different crystal types disclosed in the following patents are known. For example, JP-A Nos. 61-239248, 62-670943 and 62
-272272, 63-116158 or 64-17066, JP-A-2-28265, JP-A-2-215866 and the like.

As a dispersion medium of the organic pigment usable in the present invention, there is a known dispersion medium such as methyl ethyl ketone.

In the present invention, the photosensitive layer may contain one or more known electron-accepting substances. The addition ratio of the electron-accepting substance is as follows: the organic pigment used in the present invention: electron-accepting substance = 100: 0.01 to 20 by weight
0, preferably 100: 0.1 to 100. Further, the addition ratio of the electron accepting substance is 100: 0.01 to 100, preferably 100: 0.1 to 50, in terms of the weight ratio of total CTM: electron accepting substance.

Organic amines can be added to the photosensitive layer for the purpose of improving the charge generation function of CGM (carrier generating substance), and it is particularly preferable to add a secondary amine. These compounds are described in JP-A Nos. 59-218447 and 62-81.
No. 60.

In the photosensitive layer, for example, an antioxidant disclosed in JP-A-63-18354 can be added for the purpose of preventing ozone deterioration. The addition amount of the antioxidant is 0.1 to 100 parts by weight, preferably 1 to 50 parts by weight, particularly preferably 5 to 25 parts by weight, based on 100 parts by weight of CTM.

The photoreceptor according to the present invention may further contain, if necessary, an ultraviolet absorber or the like for the purpose of protecting the photosensitive layer, or may contain a dye for correcting color sensitivity.

An intermediate layer may be provided between the photosensitive layer and the support, and this intermediate layer functions as an adhesive layer or a blocking layer.

In the present invention, when the photosensitive layer has a two-layer structure as shown in FIG. 1, the CGL (carrier generation layer) is directly or optionally on the conductive support or CTL (carrier transport layer). Alternatively, it can be formed by the following method after providing an intermediate layer such as a blocking layer.

(1) Vacuum evaporation method

(2) Method of applying a solution in which CGM is dissolved in an appropriate solvent

(3) A method of applying a dispersion obtained by mixing and dispersing CGM into fine particles in a dispersion medium by a ball mill, sand grinder or the like, if necessary, with a binder.

That is, specifically, a vapor deposition method such as vacuum evaporation, sputter rig, or CVD, or a coating method such as dipping, spray, blade, or roll method is arbitrarily used.

The thickness of the CGL thus formed is preferably 0.01 μm to 5 μm, more preferably 0.05 μm to 3 μm.

The CTL can be formed in the same manner as the CGL. Although the thickness of the CTL can be changed as required, it is usually preferably 5 μm to 60 μm.

The composition ratio of the CTL is preferably 0.1 to 5 parts by weight with respect to 1 part by weight of the CTM of the present invention. However, when the photosensitive layer 4 in which fine-grained CGM is dispersed is formed, CGM1 is preferably used. It is preferable to use the binder in a range of 5 parts by weight or less based on parts by weight. In the case where the CGL is configured as a dispersion medium in a binder, the binder is preferably used in an amount of 5 parts by weight or less based on 1 part by weight of the CGM.

The electrophotographic photoreceptor according to the present invention has the above-mentioned constitution, and as is apparent from the examples described later, is excellent in charging characteristics, sensitivity characteristics, image forming characteristics, etc. Less fatigue deterioration when
It has excellent durability.

Further, the electrophotographic photosensitive member based on the present invention is widely used in application fields such as a photosensitive member of a printer using a laser, a cathode ray tube (CRT), and a light emitting diode (LED) as a light source, in addition to an electrophotographic copying machine. Can be. Further, the present invention can be applied to EL (electroluminescence) and the like in addition to the photoconductor.

[Examples] Examples of the present invention will be specifically described below, but the embodiments of the present invention are not limited thereto.

Example 1 30 g of a polyamide copolymerized with a monomer composition of ε-amino-caproic acid, adipic acid and N- (β-aminoethyl) piperazine at a ratio of 1: 1: 1 was heated to 50 ° C.
It was added to 800 ml of methanol EL standard (200 ml, manufactured by Kanto Chemical Co., Ltd.). Thereafter, dip coating was performed on an aluminum drum having a diameter of 80 mm to form an intermediate layer having a thickness of 0.6 μm.

Next, 20 g of a fluorenone-based disazo pigment (exemplified compound F ₁ -23) as CGM and 10 g of polyvinyl butyral resin Esrec BX-1 (manufactured by Sekisui Chemical Co., Ltd.) as methyl ethyl ketone (manufactured by Kanto Chemical Co., Ltd.)
(EL standard) was dissolved in 1000 ml, and milled in a sand mill for 24 hours to obtain a CGL coating solution. This was dip-coated on the intermediate layer to form a 0.2 μm thick CGL.

Then, the exemplified compound <10> was used as CTM.
140 g and polycarbonate resin "Iupilon Z-200"
165 g (Mitsubishi Gas Chemical Co., Ltd.) was dissolved in 1,000 ml of 1,2-dichloroethane special grade (Kanto Chemical Co., Ltd.), and CTL
A coating liquid was obtained.

After dip coating this on the above-mentioned CGL, 100 ° C.
For 1 hour to form a CTL having a thickness of 23 μm. Thus, a photoreceptor 1 comprising the intermediate layer-CGL-CTL sequentially laminated was prepared.

Examples 2 to 10 Photoconductors 2 to 10 were prepared in the same manner as in Example 1 except that CGM and CTM were changed to the exemplified compounds shown in Table 1 below.

Comparative Examples 1-2 As shown in Table 1 below, comparative photoreceptors were prepared in the same manner as in Example 1 except that the CTM of Example 1 was changed to comparative compounds <1> and <2> described below. .

Example 11 An intermediate layer was formed in the same manner as in Example 1.

As CGM, 20 g of a polycyclic quinone pigment (exemplary compound; Q _1-3 ) and 10 g of a polycarbonate resin C-1300 (manufactured by Teijin Chemicals Limited) as a binder were mixed with 1,2-
It was dissolved in dichloroethane special grade (manufactured by Kanto Chemical Co., Ltd.) and milled for 30 hours with a ball mill to obtain a CGL coating solution. This was dip-coated on the intermediate layer to form a 0.6 μm thick CGL.

Next, CTL was laminated in the same manner as in Example 1 except for using CTM Exemplified Compound <10> to prepare Photoconductor <11>.

Examples 12 to 20 Photoconductors 12 to 20 were prepared in the same manner as in Example 1 except that CGM and CTM were changed to the exemplified compounds shown in Table 2 below.
It was created.

Comparative Examples 3-4 As shown in Table 2 below, Comparative Photoconductors 3-4 were prepared in the same manner as in Example 11 except that the CTM was changed to Comparative Compounds <3> and <4>. did.

[0116] Example 21 polyvinyl butyral resin (S-LEC BX-1, manufactured by Sekisui Chemical Co., Ltd.) was a 12g dissolved in methyl ethyl ketone 1000 ml, illustrated as CGM Compound Q ₁ -3; 5.7g, Example Compound F ₁ -23; 0.5 g were mixed and dispersed with a sand grinder for 12 hours.

This was applied onto the intermediate layer described in Example 1 by dip coating to form a CGL. Further, the CTM was changed to Exemplified Compound <10> shown in Table 3, and a CTL was formed in the same manner as in Example 1. Photoconductor 21 was prepared.

Examples 22 to 30 Photoconductors 22 to 30 were prepared in the same manner as in Example 21 except that CGM and CTM were changed to the exemplified compounds shown in Table 3 below.
It was created.

Comparative Examples 5 and 6 As shown in Table 3 below, comparative photoreceptors 5 and 6 were prepared in the same manner as in Example 21 except that CTM was changed to comparative compounds <5> and <6>. did.

Example 31 50 g of the polyamide used in Example 1 was heated to 50.degree.
The solution was introduced into ml of methanol EL standard (manufactured by Kanto Chemical Co., Ltd.) and dissolved. After cooling to room temperature, 200 ml of 1-butanol special grade (Kanto Chemical Co., Ltd.) was added. Thereafter, it was dip-coated on an aluminum drum having a diameter of 80 mm to form a 0.5 μm intermediate layer.

Next, 40 g of τ-type metal-free phthalocyanine (τ-Pc) was used as CGM in a silicone resin “KR-5240”.
200 g of (solid content: 20%) (manufactured by Shin-Etsu Chemical Co., Ltd.) was added to 2000 ml of dissolved methyl ethyl ketone EL standard (manufactured by Kanto Chemical Co., Ltd.), and dispersed with a sand grinder for 4 hours to obtain a CGL coating solution. This is dip-coated on the intermediate layer and 0.4μ
An m-thick CGL was formed.

Thereafter, 135 g of Exemplified Compound <8> and 165 g of polycarbonate "Iupilon Z-200" (Mitsubishi Gas Chemical Co., Ltd.) were dissolved in 1,000 ml of 1,2-dichloroethane special grade (Kanto Chemical Co., Ltd.), and CTL coating was performed. A working liquid was obtained. This was applied onto the CGL by dip coating and then dried at 100 ° C. for 1 hour to obtain a CTL having a thickness of 22 μm. Intermediate layer, CGL and CT
A photoconductor was prepared by laminating in the order of L.

Examples 32 to 40 Photoconductors 32 to 40 were prepared in the same manner as in Example 31, except that CTM was changed to the exemplified compounds shown in Table 4 below.

Comparative Examples 7 and 8 As shown in Table 4 below, comparative photoconductors were prepared in the same manner as in Example 31, except that CTM was changed to Comparative compounds <1> and <2>.

Example 41 An interlayer-CGL-CT was prepared in the same manner as in Example 31 except that X-type metal-free phthalocyanine (X-Pc) was used for CGM.
L were sequentially laminated to prepare a photoconductor.

[0126] In Example 42 to 50 Example 41, except that the CTM as illustrative the following compounds in Table -5 created a photoreceptor 42 to 50 in the same manner as in Example 41.

Comparative Examples 9 to 10 As shown in Table 5 below, comparative photoconductors were prepared in the same manner as in Example 41, except that the CTM was changed to Comparative compounds <3> to <4>.

Example 51 Y-type oxytitanium phthalocyanine (Y-T
iOPC) [Electrophotography Society Journal 250 (2), 29 (2) , 1990] except that intermediate layer -CGL- was used in the same manner as in Example 1.
A photoconductor was prepared by sequentially laminating CTLs.

[0129] In Example 52 to 60 Example 51, except that the CTM as illustrative the following compounds in Table-6 were prepared photoreceptor 52-60 in the same manner as in Example 51.

Comparative Examples 11 and 12 As shown in Table 6 below, comparative photoconductors were prepared in the same manner as in Example 51 except that the CTM was changed to Comparative Compounds <5> and <6>.

Example 61 A photoconductor was prepared by successively laminating an intermediate layer-CGL-CTL, in the same manner as in the above example, except that a fluorenylidene-based azo CGM was used as the CGM.

Examples 62 to 70 Photoconductors 62 to 70 were prepared in the same manner as in Example 61, except that CGM and CTM were changed to the exemplified compounds shown in Table 7 below.

Comparative Examples 13 and 14 As shown in Table 7 below, comparative photoreceptors were prepared in the same manner as in Example 61 except that the CTM was changed to Comparative compounds <1> and <2>.

Example 71 30 g of a polyamide copolymerized with a monomer composition of ε-amino-caproic acid, adipic acid and N- (β-aminoethyl) piperazine at a ratio of 1: 1: 1 was heated to 50 ° C.
It was added to 800 ml of methanol EL standard (200 ml, manufactured by Kanto Chemical Co., Ltd.). Thereafter, dip coating was performed on an aluminum drum having a diameter of 80 mm to form an intermediate layer having a thickness of 0.6 μm.

Next, 20 g of a fluorenone-based disazo pigment (exemplified compound F ₁ -23) as CGM and 10 g of polyvinyl butyral resin Esrec BX-1 (manufactured by Sekisui Chemical Co., Ltd.) as methyl ethyl ketone (manufactured by Kanto Chemical Co., Ltd.) were used as binders.
(EL standard) was dissolved in 1000 ml, and milled in a sand mill for 24 hours to obtain a CGL coating solution. This was dip-coated on the intermediate layer to form a 0.2 μm thick CGL.

Then, 140 g of Exemplified Compound (6) and 165 g of polycarbonate resin "Iupilon Z-200" (manufactured by Mitsubishi Gas Chemical Co., Ltd.) were dissolved in 1000 ml of 1,2-dichloroethane special grade (manufactured by Kanto Chemical Co., Ltd.), and CTL was dissolved. A coating liquid was obtained.
This was dip-coated on the above-mentioned CGL and dried at 100 ° C. for 1 hour to form a CTL having a thickness of 23 μm. In this way, a photoreceptor 71 was formed by sequentially laminating the intermediate layer-CGL-CTL.

Examples 72 to 80 Photoconductors 72 to 80 were prepared in the same manner as in Example 71 except that CGM and CTM were changed to the exemplified compounds shown in Table 8 below.

Comparative Examples 15 and 16 As shown in Table 8 below, comparative photoconductors were prepared in the same manner as in Example 71 except that the CTM of Example 71 was changed to comparative compounds (1) and (2) described later. .

Example 81 An intermediate layer was formed in the same manner as in Example 71. As CGM, 20 g of a polycyclic quinone pigment (exemplary compound; Q _1-3 ) and a polycarbonate resin C-1300 as a binder
10 g (manufactured by Teijin Chemicals Ltd.) was dissolved in 1,2-dichloroethane special grade (manufactured by Kanto Chemical Co., Ltd.) and milled for 30 hours with a ball mill to obtain a CGL coating solution. This was dip-coated on the intermediate layer to form a 0.6 μm thick CGL.

Next, CTL was laminated in the same manner as in Example 71, except that CTM was used as the exemplary compound (2), to thereby prepare a photoreceptor 81.

Examples 82 to 90 Photoconductors 82 to 90 were prepared in the same manner as in Example 71, except that CGM and CTM were changed to the exemplified compounds shown in Table 9 below.
It was created.

Comparative Examples 17 to 18 As shown in Table 9 below, comparative photoreceptors 17 to 18 were prepared in the same manner as in Example 71 except that the CTM was changed to the comparative compounds (3) to (4). did.

[0143] Example 91 polyvinyl butyral resin (S-LEC BX-1, manufactured by Sekisui Chemical Co., Ltd.) was a 12g dissolved in methyl ethyl ketone 1000 ml, illustrated as CGM Compound Q ₁ -3; 5.7g, Example Compound F ₁ -23; 0.5 g were mixed and dispersed with a sand grinder for 12 hours.

This was dip-coated on the intermediate layer described in Example 71 to form a CGL.
Was formed to form the photoreceptor 91.

Examples 92-100 Photoconductors 92-10 were prepared in the same manner as in Example 81, except that CGM and CTM were changed to the exemplified compounds shown in Table 10 below.
Created 0.

Comparative Examples 19 to 20 As shown in Table 10 below, comparative photoconductors 19 to 20 were prepared in the same manner as in Example 91 except that CTM was used as the comparative compounds (5) to (6). did.

Example 101 50 g of the polyamide used in Example 71 was heated to 50 ° C.
The solution was introduced into ml of methanol EL standard (manufactured by Kanto Chemical Co., Ltd.) and dissolved. After cooling to room temperature, 200 ml of 1-butanol special grade (Kanto Chemical Co., Ltd.) was added. Thereafter, it was dip-coated on an aluminum drum having a diameter of 80 mm to form a 0.5 μm intermediate layer.

Next, as CGM, 40 g of τ-type metal-free phthalocyanine (τ-Pc) was added to a silicone resin “KR-5240”.
200 g of (solid content: 20%) (manufactured by Shin-Etsu Chemical Co., Ltd.) was added to 2000 ml of dissolved methyl ethyl ketone EL standard (manufactured by Kanto Chemical Co., Ltd.), and dispersed with a sand grinder for 4 hours to obtain a CGL coating solution. This is dip-coated on the intermediate layer and 0.4μ
An m-thick CGL was formed.

Thereafter, 135 g of Exemplified Compound (20) and 165 g of polycarbonate "Iupilon Z-200" (Mitsubishi Gas Chemical Co., Ltd.) were dissolved in 1000 ml of 1,2-dichloroethane special grade (manufactured by Kanto Chemical Co., Ltd.), and CTL coating was performed. A working liquid was obtained. This was applied onto the CGL by dip coating and then dried at 100 ° C. for 1 hour to obtain a CTL having a thickness of 22 μm. Intermediate layer, CGL and CT
A photoconductor was prepared by laminating in the order of L.

Examples 102 to 110 Photoconductors 102 to 110 were prepared in the same manner as in Example 101 except that the CTM was changed to the exemplified compounds shown in Table 11 below.
It was created.

Comparative Examples 21 to 22 As shown in Table 11 below, comparative photoreceptors were prepared in the same manner as in Example 101 except that CTM was used as the comparative compounds (1) and (2).

Example 111 Intermediate layer-CGL-C was prepared in the same manner as in Example 101 except that X-type metal-free phthalocyanine (X-Pc) was used for CGM.
A photoconductor was formed by sequentially stacking TLs.

Examples 112 to 120 Photoconductors 112 to 120 were prepared in the same manner as in Example 111 except that the CTM was changed to the exemplified compounds shown in Table 12 below.
It was created.

Comparative Examples 23 to 24 As shown in Table 12 below, comparative photoreceptors were prepared in the same manner as in Example 111 except that the CTM was changed to Comparative compounds (3) to (4).

Example 121 Y-type oxytitanium phthalocyanine (TiO
A photoconductor was prepared by sequentially laminating the intermediate layer-CGL-CTL in the same manner as in Example 101 except that (PC) (described above) was used.

Examples 112 to 130 Photoconductors 112 to 130 were prepared in the same manner as in Example 121, except that the CTM was changed to the exemplified compounds shown in Table 13 below.
It was created.

Comparative Examples 25 to 26 As shown in Table 13 below, comparative photoconductors were prepared in the same manner as in Example 121 except that the CTM was changed to Comparative compounds (5) and (6).

Example 131 A photoconductor was prepared by sequentially laminating an intermediate layer-CGL-CTL in the same manner as in Example 101 except that fluorenylidene-based azo CGM was used for CGM.

Examples 132 to 140 Photoconductor 13 was prepared in the same manner as in Example 131, except that CGM and CTM were changed to the exemplified compounds shown in Table 14 below.
2 to 140 were created.

Comparative Examples 27 to 28 As shown in Table 14 below, comparative photoconductors were prepared in the same manner as in Example 131 except that CTM was used as the comparative compounds (1) and (2).

Table 1 Example No. Photoconductor No. CGM CTM No. Example 1 photoreceptor 1 compound F ₁ -23 exemplified compound <10> example 2 photoconductor 2 compound 〃 exemplified compound <2> example 3 photoconductor 3 compound 〃 exemplified compound <4> example 4 photoconductor 4 compound 〃 exemplified compound <11> example 5 photoconductor 5 compound 〃 exemplified compound <13> example 6 photoreceptor 6 compound F ₁ -1 exemplified compound <16> example 7 photoreceptor 7 compound 〃 exemplified compound <17> example 8 photoconductor 8 compound 〃 exemplified compound <19> example 9 photoreceptor 9 compound F ₁ -7 exemplified compound <61> example 10 photoreceptor 10 compound F ₁ -16 exemplified compound <110> Comparative example 1 Comparative photosensitive member 1 compound F ₁ -23 Comparative compound <1> Comparative example 2 Comparative photoreceptor 2 Compound 比較 Comparative compound <2>

Table-2 Example No. Photoconductor No. CGM CTM No. Example 11 photoconductor 11 compound Q ₁ -3 exemplified compound <10> example 12 photoreceptor 12 compound 〃 exemplified compound <6> example 13 photoconductor 13 compound 〃 exemplified compound <19> example 14 photoconductor 14 compound 〃 exemplified compound <20> Example 15 Photoreceptor 15 Compound 〃 Exemplified Compound <22> Example 16 Photoreceptor 16 Compound 〃 Exemplified Compound <30> Example 17 Photoreceptor 17 Compound 〃 Exemplified Compound <35> Example 18 Photoreceptor 18 Compound 〃 Exemplified Compound <60> Example 19 Photoreceptor 19 Compound 〃 Exemplified Compound <65> Example 20 Photoreceptor 20 Compound 〃 Exemplified Compound <108> Comparative Example 3 Comparative Photoreceptor 3 Compound 比較 Comparative Compound <3> Comparative Example 4 Comparative Photosensitivity Compound 4 〃 Comparative compound <4>

Table 3 Example No. Photoconductor No. CGM CTM No. example 21 photoconductor 21 compound F ₁ -23 Q ₁ -3 exemplified compound <10> example 22 photoconductor 22 compound 〃 exemplified compound <2> example 23 photoconductor 23 compound 〃 exemplified compound <4> example 24 a photosensitive body 24 compound 〃 exemplified compound <18> example 25 photoconductor 25 compound 〃 exemplified compound <21> example 26 photoconductor 26 compound F ₁ -1 Q ₁ -3 exemplified compound <33> example 27 photoconductor 27 compound 〃 exemplified compound <62> example 28 photoconductor 28 compound 〃 exemplified compound <70> example 29 photoconductor 29 compound F ₁ -7 Q ₁ -3 exemplified compound <75> example 30 photoconductor 30 compound F ₁ -16 Q ₁ -3 exemplified compound <98> Comparative example 5 Comparative photoreceptor 5 compound F ₁ -23 Q ₁ -3 comparative compound <5> Comparative example 6 Comparative photosensitive 6 Compound 〃 comparative compound <6>

Table-4 Example No. Photoconductor No. CGM CTM No. ── Example 31 Photoconductor 31 compound τ-type metal-free lid Exemplary compound <8> Russianin Example 32 Photoconductor 32 compound 例 示 Exemplary compound <10> Example 33 Photoconductor 33 compound 例 示 Exemplary compound <13> Example 34 Photosensitivity Compound 34 Compound 〃 Exemplary Compound <20> Example 35 Photoconductor 35 Compound 例 示 Exemplary Compound <25> Example 36 Photoconductor 36 Compound 〃 Exemplary Compound <88> Example 37 Photoconductor 37 Compound 例 示 Exemplary Compound <93> Example 38 Photoconductor 38 Compound Exemplary Compound <103 Example 39 Photoconductor 39 Compound 例 示 Exemplary Compound <109> Example 40 Photoconductor 40 Compound 例 示 Exemplary Compound <114> Comparative Example 7 Comparative Photoconductor 7 Compound 比較 Comparative Compound <1> Comparative Example 8 Comparative Photoconductor 8 Compound 〃 Comparative Compound <2>

Table 5 Example No. Photoconductor No. CGM CTM II Example 41 Photoconductor 41 compound X-type metal-free lid Exemplary compound <3> Russianin Example 42 Photoconductor 42 compound 例 示 Exemplary compound <10> Example 43 Photoconductor 43 compound 例 示 Exemplary compound <12> Example 44 Photoconductor 44 compound 〃 Exemplified Compound <17> Example 45 Photoconductor 45 Compound 例 示 Exemplified Compound <23> Example 46 Photoconductor 46 Compound 例 示 Exemplified Compound <44> Example 47 Photoconductor 47 Compound 例 示 Exemplified Compound <51> Example 48 Photoconductor 48 Compound 例 示 Exemplified Compound <63> Example 49 Photoreceptor 49 Compound 例 示 Exemplified Compound <92> Example 50 Photoreceptor 50 Compound 例 示 Exemplified Compound <101> Comparative Example 9 Comparative Photoreceptor 9 Compound 〃 Comparative Compound <3> Comparative Example 10 Comparative photoconductor 10 compounds Comparative compound <4>

Table-6 Example No. Photoconductor No. CGM CTM No. ─ Example 51 Photoconductor 51 Compound Y-type Oxytitanium Exemplary Compound <1> Muphthalocyanine Example 52 Photoconductor 52 Compound 例 示 Exemplary Compound <6> Example 53 Photoconductor 53 Compound 〃 Exemplary Compound <7> Example 54 Photoconductor 54 Compound 〃 Exemplified Compound <9> Example 55 Photoreceptor 55 Compound 例 示 Exemplified Compound <10> Example 56 Photoreceptor 56 Compound 例 示 Exemplified Compound <27> Example 57 Photoreceptor 57 Compound 〃 Exemplified Compound <38> Example 58 Photosensitive Compound 58 Compound 〃 Exemplified Compound <40> Example 59 Photoreceptor 59 Compound 例 示 Exemplified Compound <55> Example 60 Photoreceptor 60 Compound 〃 Exemplified Compound <77> Comparative Example 11 Comparative Photoreceptor 11 Compound 比較 Comparative Compound <5> Compare Example 12 Comparative Photoconductor 12 Compound 比較 Comparative Compound <6>

Table-7 Example No. Photoconductor No. CGM CTM ─────────────────────────────── Example 61 photoreceptor 61 compound F ₂ -6 exemplified compound <2> example 62 photoconductor 62 compound 〃 exemplified compound <4> example 63 photoconductor 63 compound 〃 exemplified compound <6> example 64 photoconductor 64 compound 〃 exemplified compound <15> Example 65 Photoreceptor 65 Compound 〃 Exemplified Compound <25> Example 66 Photoreceptor 66 Compound 例 示 Exemplified Compound <35> Example 67 Photoreceptor 67 Compound 例 示 Exemplified Compound <47> Example 68 Photoreceptor 68 Compound 例 示 Exemplified compound <58> example 69 photoconductor 69 compound F ₂ -3 exemplified compound <69> example 70 photoconductor 70 compound F ₂ -5 exemplified compound <80> Comparative example 13 Comparative photoreceptor 13 compound F ₂ -6 Comparative compound <1> Comparative Example 14 Comparative Photoreceptor 14 Compound 比較 Comparative Compound <2>

Table 8 Example No. Photoconductor No. CGM CTM No. Example 71 photoconductor 71 compound F ₁ -23 exemplified compound (6) example 72 photoconductor 72 compound 〃 exemplary compound (8) example 73 photoconductor 73 compound 〃 exemplary compound (11) example 74 photoconductor 74 compound 〃 exemplified compound (20) example 75 photoconductor 75 compound 〃 exemplary compound (25) example 76 photoconductor 76 compound F ₁ -1 exemplified compound (35) example 77 photoconductor 77 compound 〃 exemplary compound (49) example 78 photoconductor 78 compound 〃 exemplified compound (102) example 79 photoconductor 79 compound F ₁ -7 exemplified compound (133) example 80 photoconductor 80 compound F ₁ -16 exemplified compound (293) Comparative example 15 Comparative photoreceptor 15 compound F ₁ -23 Comparative compound (1) Comparative example 16 Comparative photoreceptor 16 Compound 〃 Comparative compound (2)

Table-9 Example No. Photoconductor No. CGM CTM ──────────────────────────────── Example 81 photoconductor 81 compound Q ₁ -3 exemplified compound (2) example 82 photoconductor 82 compound 〃 exemplary compound (5) example 83 photoconductor 83 compound 〃 exemplary compound (8) example 84 photoconductor 84 compound 〃 exemplified compound (15) Example 85 Photoconductor 85 Compound Exemplary Compound (21) Example 86 Photoconductor 86 Compound 例 示 Exemplary Compound (33) Example 87 Photoconductor 87 Compound 例 示 Exemplary Compound (66) Example 88 Photoconductor 88 Compound 〃 Illustrative Compound (80) Example 89 Photoreceptor 89 Compound 例 示 Illustrative Compound (102) Example 90 Photoreceptor 90 Compound 例 示 Illustrative Compound (163) Comparative Example 17 Comparative Photoreceptor 17 Compound 〃 Comparative Compound (3) Comparative Example 18 Comparative Photosensitivity Compound 18 〃 Comparative compound (4)

Table-10 Example No. Photoconductor No. CGM CTM No. Example 91 Photoconductor 91 Compound F ₁ -23 Q _1-3 Example Compound (7) Example 92 Photoconductor 92 Compound 例 示 Example Compound (11) Example 93 Photoconductor 93 Compound 〃 Example Compound (23) Example 94 Photosensitivity body 94 compound 〃 exemplary compound (42) example 95 photoconductor 95 compound 〃 exemplary compound (67) example 96 photoconductor 96 compound F ₁ -1 Q ₁ -3 exemplified compound (88) example 97 photoconductor 97 compound 〃 exemplified compound (91) example 98 photoconductor 98 compound 〃 exemplified compound (107) example 99 photoconductor 99 compound F ₁ -7 Q ₁ -3 exemplified compound (123) example 100 photosensitive member 100 compound F ₁ -16 Q ₁ -3 exemplified compound (191) Comparative example 19 Comparative photoreceptor 19 compound F ₁ -23 Q ₁ -3 Comparative compound (5) Comparative example 20 Comparative photoreceptor 20 compound 〃 comparative compound (6)

Table-11 Example No. Photoconductor No. CGM CTM ─────────────────────────────────── ─ Example 101 Photoconductor 101 compound τ-type metal-free lid Exemplary compound (20) Russianin Example 102 Photoconductor 102 compound 例 示 Exemplary compound (27) Example 103 Photoconductor 103 compound 例 示 Exemplary compound (33) Example 104 Photoconductor 104 Compound 例 示 Exemplified Compound (44) Example 105 Photoreceptor 105 Compound 〃 Exemplified Compound (53) Example 106 Photoreceptor 106 Compound 例 示 Exemplified Compound (96) Example 107 Photoreceptor 107 Compound 例 示 Exemplified Compound (102) Example 108 Photoconductor 108 Compound 例 示 Exemplary Compound (133) Example 109 Photoconductor 109 Compound 例 示 Exemplary Compound (173) Example 110 Photoconductor 110 Compound 例 示 Exemplary Compound (202) Comparative Example 21 Comparative Photoconductor 21 Compound 比較 Comparative Compound (1) Comparative Example 22 Comparative Photoconductor 22 Compound 〃 Comparative Compound (2)

Table-12 Example No. Photoconductor No. CGM CTM II Example 111 Photoconductor 111 Compound X-Type Metal-Free Lid Example Compound (2) Russianine Example 112 Photoconductor 112 Compound 例 示 Example Compound (8) Example 113 Photoconductor 113 Compound 例 示 Example Compound (14) Example 114 Photoconductor 114 Compound 〃 Exemplified compound (31) Example 115 Photoreceptor 115 compound 〃 Exemplified compound (53) Example 116 Photoreceptor 116 compound 例 示 Exemplified compound (77) Example 117 Photoreceptor 117 compound 〃 Exemplified compound (86) Example 118 Photoreceptor 118 Compound 例 示 Exemplified Compound (98) Example 119 Photoreceptor 119 Compound 例 示 Exemplified Compound (103) Example 120 Photoreceptor 120 Compound 例 示 Exemplified Compound (217) Comparative Example 23 Comparative Photoreceptor 23 Compound 〃 Comparative Compound (3) Comparative Example 24 Comparative photoreceptor 24 compounds 〃 Comparative compound (4)

Table 13 Example No. Photoconductor No. CGM CTM No. ─ Example 121 Photoreceptor 121 Compound Y-type Oxytitanium Exemplified Compound (11) Muphthalocyanine Example 122 Photoreceptor 122 Compound 例 示 Exemplified Compound (35) Example 123 Photoreceptor 123 Compound 〃 Exemplified Compound (43) Example 124 Photoreceptor 124 Compound 〃 Exemplified Compound (60) Example 125 Photoreceptor 125 Compound 例 示 Exemplified Compound (105) Example 126 Photoreceptor 126 Compound 〃 Exemplified Compound (118) Example 127 Photoreceptor 127 Compound 〃 Exemplified Compound (133) Example 128 Photosensitive Compound 128 Compound 例 示 Exemplified Compound (183) Example 129 Photoreceptor 129 Compound 〃 Exemplified Compound (228) Example 130 Photoreceptor 130 Compound 例 示 Exemplified Compound (261) Comparative Example 25 Comparative Photoreceptor 25 Compound 〃 Comparative Compound (5) Compare Example 26 Comparative photoreceptor 26 Compound 比較 Comparative compound (6)

Table-14 Example No. Photoconductor No. CGM CTM 例 Example 131 photoreceptor 131 compound F ₂ -6 exemplified compound (3) example 132 photoreceptor 132 compound 〃 exemplary compound (18) example 133 photoreceptor 133 compound 〃 exemplary compound (23) example 134 photoreceptor 134 compound 〃 exemplary compound ( 39) Example 135 Photoconductor 135 Compound 例 示 Exemplary Compound (48) Example 136 Photoconductor 136 Compound 例 示 Exemplary Compound (75) Example 137 Photoconductor 137 Compound 例 示 Exemplary Compound (91) Example 138 Photoconductor 138 Compound 例 示 Exemplary compound (103) example 139 photoreceptor 139 compound F ₂ -3 exemplified compound (119) example 140 photoreceptor 140 compound F ₂ -5 exemplified compound (137) Comparative example 27 Comparative photoreceptor 27 compound F ₂ -6 Comparative compound (1) Comparative Example 28 Comparative Photoconductor 28 Compound 〃 Comparative Compound (2)

(Evaluation Example 1) Konica Copier U-Bi
x5076 remodeling machine (band electrode changed to negative charge, exposure amount 4.65 l)
ux), the linear potential was set to 240, 330, and 440 mm / sec in three steps, and the residual potential Vr was measured when charging and exposure were repeated 20,000 times. The results are as shown in Tables 15 to 17 below. The photoreceptor using the CTM of the present invention did not have a large residual potential when the linear velocity was increased, and exhibited excellent high-speed performance. showed that. Note that the initial blank paper potential (V
w) is as shown in Tables 15 to 17 below.

(Evaluation Example 2) Using the same modified Konica Copier U-Bix 5076 as used in Evaluation Example 1,
A continuous copy test was performed 100,000 times using recycled paper No. 4. The results are shown in Tables 18 to 20 below. The photoreceptor using the compound of the present invention had a good image up to 100,000 times, but the photoreceptor using the comparative photoreceptor had 20,000 to 30,000 times. As a result, several white spots appeared on the solid black part. In addition, the evaluation of the white spot was A4
The number of white spots generated on the solid black image was visually counted. The results are shown in Tables 18 to 20 below.

(Evaluation Example 3) Using Konica Digital Copy U-Bix8028, normal temperature (25 ° C.) and low temperature (10 ° C.)
, The unexposed portion potential VH and the exposed portion potential VL were measured. The results are shown in Tables 21 to 24 below.

(Evaluation Example 4) The same digital copy U-Bix8028 manufactured by Konica Corporation as used in Evaluation Example 3 was loaded with a developing unit, an image was output several times, and black spots on a white background portion of the copied image were obtained. Was evaluated. The results are shown in Tables 25 to 28 below.

The black spots were evaluated by measuring the particle size and the number of black spots using an image analyzer “Omnikon 300” (manufactured by Shimadzu Corporation).
Judgment was made based on the number of pieces per ² pieces. The criteria for black spot evaluation are as shown in the table below.

[0180] When the result of the black spot determination is ◎ or ○, it is practical, but Δ is not suitable for practical use, and when it is ×, it is not practical.

Table-15 Initial Vr (v) blank paper potential after repetition of 20,000 times at the following linear velocity Photoconductor No. Vw (v) 240mm / sec 330mm / sec Repetition at 440mm / sec. ────────────────────────────── Photoconductor 1 49 10 16 20 Photoconductor 2 50 11 18 21 Photoconductor 3 51 10 15 20 Photoconductor 4 53 12 15 19 Photoconductor 5 54 15 14 23 Photoconductor 6 54 10 17 26 Photoconductor 7 52 11 18 25 Photoconductor 8 55 13 17 24 Photoconductor 9 47 14 16 27 Photoconductor 10 50 10 17 26 Comparative photoreceptor 1 68 16 43 79 Comparative photoreceptor 2 72 19 49 85

Table-16 Initial Vr (v) Blank paper potential after repetition of 20,000 times at the following linear speed Photoconductor No. Vw (v) 240mm / sec 330mm / sec Repeat at 440mm / sec. ─────────────────────────────── Photoconductor 11 100 10 12 21 Photoconductor 12 104 13 15 26 Photoconductor 13 96 12 16 23 Photoconductor 14 94 9 15 23 Photoconductor 15 98 11 14 25 Photoconductor 16 100 12 18 26 Photoconductor 17 102 11 16 22 Photoconductor 18 104 12 14 27 Photoconductor 19 103 10 13 30 Photoconductor 20 95 9 17 34 Comparative photoconductor 3 116 12 43 83 Comparative photoconductor 4 121 15 40 81

Table-17 Initial Vr (v) blank paper potential after repetition of 20,000 times at the following linear velocity Photoconductor No. Vw (v) 240mm / sec 330mm / sec Repeated at 440mm / sec. ────────────────────────────── Photoconductor 21 73 10 16 22 Photoconductor 22 66 11 15 24 Photoconductor 23 73 13 16 24 Photoconductor 24 63 10 15 19 Photoconductor 25 71 9 18 24 Photoconductor 26 70 12 15 26 Photoconductor 27 71 13 14 24 Photoconductor 28 69 15 17 25 Photoconductor 29 72 15 20 25 Photoconductor 30 74 18 20 29 Comparative photoreceptor 5 83 17 41 79 Comparative photoreceptor 6 94 19 40 85

Table-18 Photoconductor No. Number of white spots after 10,000 times 100,000 times after 50,000 times Number of white spots Number of white spots ───────────── ──────────── Photoconductor 1 000 Photoconductor 2 000 Photoconductor 3 0 1 2 Photoconductor 4 000 Photoconductor 500 000 Photoconductor 6 000 Photoconductor 7 0 1 2 Photoreceptor 8 0 0 0 Photoreceptor 9 0 0 0 Photoreceptor 10 0 0 0 Comparative photoreceptor 1 6 22 43 Comparative photoreceptor 2 5 20 38

Table 19 Photoconductor No. Number of white spots after 10,000 times 100,000 times after 50,000 times Number of white spots Number of white spots ───────────── ──────────── Photoreceptor 1100 Photoreceptor 12000 Photoreceptor 1300 2 Photoreceptor 1400 2 Photoreceptor 1 50 1 2 Photoreceptor 1600 Photoreceptor 17 000 Photoconductor 18 000 Photoconductor 19 01 2 Photoconductor 2 000 Comparative photoconductor 3 8 20 45 Comparative photoconductor 4 6 25 49

Table-20 Photoconductor No. Number of white spots after 10,000 times 100,000 times after 50,000 times Number of white spots Number of white spots ───────────── ──────────── Photoconductor 2100 Photoconductor 2200 1 Photoconductor 2300 Photoconductor 24000 Photoconductor 25 0 1 2 Photoconductor 26 00 Photoconductor 27 000 Photoconductor 28 000 Photoconductor 29 001 Photoconductor 30 00 000 Comparative photoconductor 5 3 20 38 Comparative photoconductor 6 3 18 36

Table 21 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ────────────── ───────── Photoconductor 31 702 102 703 104 Photoconductor 32 709 98 702 103 Photoconductor 33 710 100 712 100 Photoconductor 34 690 108 710 102 Photoconductor 35 700 101 700 108 Photoconductor 36 702 105 701 105 Photoconductor 37 705 115 709 103 Photoconductor 38 695 112 715 107 Photoconductor 39 710 111 712 110 Photoconductor 40 705 113 720 115 Comparative photoconductor 7 702 120 683 170 Comparative photoconductor 8 690 124 686 178

Table 22 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ────────────── ───────── Photoconductor 41 703 108 703 104 Photoconductor 42 704 102 703 105 Photoconductor 43 707 105 700 103 Photoconductor 44 706 102 712 99 Photoconductor 45 710 115 706 106 Photoconductor 46 720 104 715 105 Photoconductor 47 718 100 710 111 Photoconductor 48 705 112 715 109 Photoconductor 49 702 110 706 110 Photoconductor 50 715 115 707 113 Comparative photoconductor 9 708 122 680 170 Comparative photoconductor 10 709 123 690 178

Table 23 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ────────────── ───────── Photoconductor 51 704 52 704 50 Photoconductor 52 705 54 708 53 Photoconductor 53 705 53 706 52 Photoconductor 54 703 50 710 50 Photoconductor 55 708 55 708 47 Photoconductor 56 702 49 708 51 Photoconductor 57 698 53 699 53 Photoconductor 58 706 50 700 48 Photoconductor 59 710 51 711 52 Photoconductor 60 713 55 715 56 Comparative photoconductor 11 715 62 685 91 Comparative photoconductor 12 717 60 686 81

Table 24 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ────────────── ───────── Photoconductor 61 699 102 700 104 Photoconductor 62 701 107 702 105 Photoconductor 63 700 99 705 104 Photoconductor 64 715 103 700 109 Photoconductor 65 704 102 705 103 Photoconductor 66 715 104 709 109 Photoconductor 67 705 98 715 103 Photoconductor 68 708 106 708 108 Photoconductor 69 712 111 712 102 Photoconductor 70 710 100 713 105 Comparative photoconductor 13 718 123 689 153 Comparative photoconductor 14 709 118 686 142

Table 25: 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 31 ◎ ◎ ◎ Photoconductor 32 ◎ ◎ ◎ Photoconductor 33 ◎ ◎ ◎ Photoconductor 34 ◎ ◎ ◎ Photoconductor 35 ◎ ○ ○ Photoconductor 36 ◎ ○ ○ Photoconductor 37 ◎ ○ ○ Photoconductor 38 ◎ ◎ ○ Photoconductor 39 ◎ ○ ○ Photoconductor 40 ◎ ○ ○ Comparative photoconductor 7 ○ △ × Comparative photoconductor 8 ○ △ ×

Table-26 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 41 ◎ ◎ ◎ Photoconductor 42 ◎ ◎ ◎ Photoconductor 43 ◎ ◎ ◎ Photoconductor 44 ◎ ○ ○ Photoconductor 45 ◎ ○ ○ Photoconductor 46 ◎ ◎ ◎ Photoconductor 47 ◎ ◎ ◎ Photoconductor 48 ◎ ◎ ○ Photoconductor 49 ◎ ◎ ○ Photoconductor 50 ◎ ◎ ○ Comparative photoconductor 9 ○ △ × Comparative photoconductor 10 ○ △ △

Table 27 Copying 20,000 times Copying 50,000 times Copying 100,000 times Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 51 ◎ ◎ ○ Photoconductor 52 ◎ ◎ ◎ Photoconductor 53 ◎ ◎ ◎ Photoconductor 54 ◎ ◎ ◎ Photoconductor 55 ◎ ◎ ◎ Photoconductor 56 ◎ ◎ ◎ Photoconductor 57 ◎ ◎ ○ Photoconductor 58 ◎ ◎ ◎ Photoconductor 59 ◎ ◎ ◎ Photoconductor 60 ◎ ◎ ◎ Comparative photoconductor 11 ○ △ × Comparative photoconductor 12 ○ △ ×

Table-28 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 61 ◎ ◎ ◎ Photoconductor 62 ◎ ○ ○ Photoconductor 63 ◎ ◎ ◎ Photoconductor 64 ◎ ◎ ◎ Photoconductor 65 ◎ ○ ○ Photoconductor 66 ◎ ◎ ◎ Photoconductor 67 ◎ ◎ ◎ Photoconductor 68 ◎ ◎ ◎ Photoconductor 69 ◎ ◎ ◎ Photoconductor 70 ◎ ○ ○ Comparative photoconductor 13 ○ △ △ Comparative photoconductor 14 ○ △ ×

As described above, when the electrophotographic photosensitive member according to the present invention is repeatedly used after being incorporated in a copying machine, a printer, or the like, it has high sensitivity and is free from image defects such as white spots, black spots, fog, and reduced density. A good image free from image defects can be obtained.

Further, the electrophotographic photoreceptor according to the present invention has a small residual potential and can provide a good image free from image defects and poor image quality even when used repeatedly in a high-speed copying machine or printer.

Next, the same evaluation as described above was carried out for Examples 71 to 140 and Comparative Examples 15 to 28.
The results shown in Table 42 were obtained.

Table-29 Initial Vr (v) blank paper potential after repetition of 20,000 times at the following linear velocity Photoconductor No. Vw (v) 240mm / sec 330mm / sec Repeated at 440mm / sec.感光 Photoconductor 71 50 10 15 25 Photoconductor 72 49 13 16 20 Photoconductor 73 50 15 15 27 Photoconductor 74 47 10 16 20 Photoconductor 75 55 10 18 19 Photoconductor 76 52 13 17 20 Photoconductor 77 54 10 15 24 Photoconductor 78 54 11 17 26 Photoconductor 79 53 14 18 25 Photoconductor 80 52 13 15 24 Comparative photoconductor 15 72 18 44 78 Comparative photoconductor 16 73 20 49 84

Table-30 Initial Vr (v) blank paper potential after repetition of 20,000 times at the following linear velocity Photoconductor No. Vw (v) 240mm / sec 330mm / sec Repeat at 440mm / sec. ────────────────────────────── Photoconductor 81 101 11 13 23 Photoconductor 82 103 10 14 28 Photoconductor 83 98 9 16 22 Photoconductor 84 95 13 15 26 Photoconductor 85 99 11 15 21 Photoconductor 86 100 9 17 29 Photoconductor 87 98 10 13 27 Photoconductor 88 102 12 16 26 Photoconductor 89 94 10 15 30 Photoconductor 90 100 12 16 29 Comparative photoreceptor 17 115 13 40 82 Comparative photoreceptor 18 120 16 40 80

Table-31 Initial Vr (v) blank paper potential after repetition of 20,000 times at the following linear velocity Photoconductor No. Vw (v) 240mm / sec 330mm / sec Repeat at 440mm / sec. ────────────────────────────── Photoconductor 91 72 15 16 24 Photoconductor 92 71 9 10 23 Photoconductor 93 69 10 15 24 Photoconductor 94 70 13 13 22 Photoconductor 95 68 15 16 29 Photoconductor 96 70 9 16 27 Photoconductor 97 71 13 15 29 Photoconductor 98 70 10 12 25 Photoconductor 99 69 9 10 22 Photoconductor 100 70 12 14 23 Comparative photoconductor 19 83 16 41 77 Comparative photoconductor 20 90 18 41 83

Table-32 Photoconductor No. Number of white spots after 10,000 times 100,000 times after 50,000 times Number of white spots Number of white spots ───────────── ──────────── Photoreceptor 7101 2 Photoreceptor 7 2 00 Photoreceptor 7 3 0 0 Photoreceptor 7 4 0 1 Photoreceptor 7 5 0 0 0 Photoreceptor 7 6 1 2 Photoreceptor 77 000 Photoconductor 780 000 Photoconductor 790 000 Photoconductor 8000 000 Comparative photoconductor 155 21 40 Comparative photoconductor 165 23 40

Table-33 Photoconductor No. Number of white spots after 10,000 times 100,000 times after 50,000 times Number of white spots Number of white spots ───────────── ──────────── Photoconductor 81 0 1 2 Photoconductor 82 00 1 Photoconductor 83 0 1 2 Photoconductor 84 000 Photoconductor 85 000 Photoconductor 86 000 Photoconductor 87 0 1 2 Photoconductor 88 000 Photoconductor 89 000 Photoconductor 90 000 Reference photoconductor 17 10 21 43 Comparative photoconductor 18 8 18 46

Table-34 Photoconductor No. Number of white spots after 10,000 times 100,000 times after 50,000 times Number of white spots Number of white spots ───────────── ──────────── Photoconductor 91 000 Photoconductor 92 0 1 2 Photoconductor 930 000 Photoconductor 940 000 Photoconductor 950 000 Photoconductor 960 001 Photoconductor 97 0 1 2 Photoconductor 98 000 Photoconductor 99 000 Photoconductor 100 000 Comparative photoconductor 19 3 21 39 Comparative photoconductor 20 4 19 35

Table-35 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ────────────── ───────── Photoconductor 101 703 101 704 103 Photoconductor 102 700 103 703 102 Photoconductor 103 709 99 710 100 Photoconductor 104 710 110 705 103 Photoconductor 105 700 100 715 107 Photoconductor 106 703 111 712 105 Photoconductor 107 698 105 720 115 Photoconductor 108 699 100 705 104 Photoconductor 109 702 105 707 110 Photoconductor 110 705 104 703 113 Comparative photoconductor 21 703 121 682 177 Comparative photoconductor 22 698 123 685 173

Table-36 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ──────────────感光 Photoconductor 111 704 107 703 105 Photoconductor 112 709 105 705 111 Photoconductor 113 706 110 710 105 Photoconductor 114 710 104 715 103 Photoconductor 115 705 103 710 106 Photoconductor 116 713 100 706 105 Photoconductor 117 704 105 709 99 Photoconductor 118 710 112 715 107 Photoconductor 119 705 103 710 108 Photoconductor 120 703 105 708 111 Comparative photoconductor 23 709 120 683 171 Comparative photoconductor 24 710 122 689 179

Table-37 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ──────────────感光 Photoconductor 121 705 51 706 45 Photoconductor 122 711 49 707 53 Photoconductor 123 705 50 708 47 Photoconductor 124 700 55 705 56 Photoconductor 125 699 58 700 53 Photoconductor 126 705 53 699 48 Photoconductor 127 711 54 695 50 Photoconductor 128 710 49 700 52 Photoconductor 129 706 50 715 50 Photoconductor 130 705 52 711 50 Comparative photoconductor 25 717 63 680 98 Comparative photoconductor 26 718 65 679 85

Table-38 Room temperature (25 ° C.) Low temperature (10 ° C.) Photoconductor No. VH (v) VL (v) VH (v) VL (v) ────────────── ───────── Photoconductor 131 700 102 702 103 Photoconductor 132 700 101 700 102 Photoconductor 133 715 108 713 109 Photoconductor 134 705 103 705 103 Photoconductor 135 709 108 700 108 Photoconductor 136 708 110 705 104 Photoconductor 137 703 106 710 105 Photoconductor 138 710 103 700 103 Photoconductor 139 705 110 708 102 Photoconductor 140 710 105 711 105 Comparative photoconductor 27 716 122 690 150 Comparative photoconductor 28 720 119 686 143

Table-39 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 101 ◎ ◎ ◎ Photoconductor 102 ◎ ◎ ◎ Photoconductor 103 ◎ ◎ ◎ Photoconductor 104 ◎ ◎ ○ Photoconductor 105 ◎ ◎ ◎ Photoconductor 106 ◎ ○ ○ Photoconductor 107 ◎ ◎ ◎ Photoconductor 108 ◎ ○ ○ Photoconductor 109 ◎ ◎ ◎ Photoconductor 110 ◎ ◎ ○ Comparative photoconductor 21 ○ △ × Comparative photoconductor 22 ○ △ ×

Table-40 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 111 ◎ ◎ ◎ Photoconductor 112 ◎ ○ ○ Photoconductor 113 ◎ ○ ○ Photoconductor 114 ◎ ◎ ◎ Photoconductor 115 ◎ ◎ ◎ Photoconductor 116 ◎ ◎ ◎ Photoconductor 117 ◎ ◎ ○ Photoconductor 118 ◎ ○ ○ Photoconductor 119 ◎ ◎ ◎ Photoconductor 120 ◎ ◎ ◎ Comparative photoconductor 23 ○ △ × Comparative photoconductor 24 ○ △ ×

Table-41 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment感光 Photoconductor 121 ◎ ◎ ◎ Photoconductor 122 ◎ ◎ ○ Photoconductor 123 ◎ ◎ ◎ Photoconductor 124 ◎ ◎ ◎ Photoconductor 125 ◎ ◎ ○ Photoconductor 126 ◎ ◎ ◎ Photoconductor 127 ◎ ◎ ◎ Photoconductor 128 ◎ ◎ ◎ Photoconductor 129 ◎ ◎ ◎ Photoconductor 130 ◎ ◎ ◎ Comparative photoconductor 25 ○ △ × Comparative photoconductor 26 ○ △ ×

Table-42 20,000 copies 50,000 copies 100,000 copies Black spot judgment after the photoreceptor after use Black spot judgment Black spot judgment Black spot judgment ───────────────── Photoconductor 131 ◎ ◎ ◎ Photoconductor 132 ◎ ○ ○ Photoconductor 133 ◎ ◎ ◎ Photoconductor 134 ◎ ◎ ◎ Photoconductor 135 ◎ ◎ ◎ Photoconductor 136 ◎ ○ ○ Photoconductor 137 ◎ ◎ ◎ Photoconductor 138 ◎ ○ ○ Photoconductor 139 ◎ ◎ ◎ Photoconductor 140 ◎ ◎ ◎ Comparative photoconductor 27 ○ △ △ Comparative photoconductor 28 ○ △ ×

Embodiment 141 Next, an embodiment in which the present invention is applied to EL (electroluminescence), which is different from the above example, will be described.

On a transparent electrode (indium-tin oxide layer) formed on a glass substrate, Exemplified Compound <23> was deposited to a thickness of 500 mm as a charge injection layer, and then an 8-quinolinol A1 complex ( Alq ₃ ) as the organic fluorescent layer
And a magnesium / silver alloy was further deposited thereon as a negative electrode.

[0214] Examination of the emission characteristics of the obtained organic thin film EL element, luminescence of 0.04mW / cm ² was obtained at 4mA / cm ^2. The emission color was yellow green.

[0215]

Table-43 No. R¹ (R^Two)_n R^3a R^3b  ─────────────────────────────── <1> 2-Br H (n = 0) HH <2> 3-Br H (〃) 〃 〃 <3> 4-Br H (〃) 〃 〃 <4> 2-FH (〃) 〃 〈<5> 3-FH (〃) 〃 〃 <6> 4-FH (〃) 〃 〈<7> 2-IH (〃) 〃 ８ <8> 3-IH (〃) 〃 〈<9> 4-IH (〃) 〃 〈<10> 2-Cl H (〃) 〃 〃 <11> 3 -Cl H (〃) 〃 〃 <12> 2-CN H (〃) 〃 〃 <13> 3-CN H (〃) 〃 〈<14> 2-Br 4-CH_Three 〃 〃 <15> 4-Br 2-CH_Three 〃 〃 <16> 4-Br 3-CH_Three 〃 〃 <17> 2-Cl 4-CH_Three 〃 〃 <18> 2-Cl 5-CH_Three 〃 〃 <19> 2-Cl 6-CH_Three 〃 〃 <20> 3-Cl 2-CH_Three 〃 〃 <21> 3-Cl 4-CH_Three 〃 〃 <22> 5-Cl 2-CH_Three 〃 〃 <23> 2-F 6-CH_Three 〃 〃 <24> 3-F 2-CH_Three 〃 〃 <25> 3-F 4-CH_Three 〃 〃 <26> 4-F 2-CH_Three 〃 〃 <27> 5-F 2-CH_Three 〃 〃 <28> 2-Cl 4-Cl 〃 〃 <29> 2-Cl 3-CH_Three, 4-Cl 〃 30 <30> 2-Cl 3-CH_Three, 6-Cl 〃 31 <31> 3-Cl 3-CH_Three, 6-CH_Three 〃 〃 <32> 3-Cl 4-Cl 〃 〃 <33> 3-Cl 2-CH_Three 〃 〃 <34> 2-Br 4-Br 〃 〈<35> 2-Br 5-CH_Three 〃 〃 <36> 2-F 3,4,5,6-F 〃 〃 <37> 2-Cl 3,4,5,6-Cl 〃 〃 <38> 2-Br 4-C_TwoH_Five 〃 〃 <39> 4-Br 4-C_ThreeH₇ 〃 〃 <40> 2-I 4-CH_Three 〃 〃 <41> 4-I 2-C_TwoH_Five 〃 〃 <42> 2-CN 4-CH_Three 〃 〃 <43> 2-CN 4-C_FourH₉ 〃 〃 <44> 3-CN 4-CH_Three 〃 〃 <45> 2-Br H (n = 0) 4-CH_Three 〃 <46> 3-Br H (〃) 〃 〈<47> 4-Br H (〃) 〃 〈<48> 2-FH (〃) 〃 〃 <49> 3-FH (〃) 〃 50 <50> 4-FH (〃) 〃 〃 <51> 2-IH (〃) 〃 〃 <52> 3-IH (〃) 〃 〈<53> 4-IH (〃) 〃 〈<54> 2-Cl H (〃 ) 〃 〈<55> 3-Cl H (〃) 〃 〃 <56> 2-CN H (〃) 〃 〈<57> 3-CN H (〃) 〃 〈<58> 2-Br 4-CH_Three 〃 〃 <59> 4-Br 2-CH_Three 〃 〃 <60> 4-Br 3-CH_Three 〃 〃 <61> 2-Cl 4-CH_Three 〃 〃 <62> 2-Cl 5-CH_Three 〃 〃 <63> 2-Cl 6-CH_Three 〃 〃 <64> 3-Cl 2-CH_Three 〃 〃 <65> 3-Cl 4-CH_Three 〃 〃 <66> 5-Cl 2-CH_Three 〃 〃 <67> 2-F 6-CH_Three 〃 〃 <68> 3-F 2-CH_Three 〃 69 <69> 3-F 4-CH_Three 〃 〃 <70> 4-F 2-CH_Three 〃 〃 <71> 5-F 2-CH_Three 〃 〃 <72> 2-Cl 4-Cl 〃 〈<73> 2-Cl 3-CH_Three, 4-Cl 〃 〃 <74> 2-Cl 5-CH_Three, 4-Cl 〃 〃 <75> 2-Cl 6-CH_Three, 4-Cl 〃 〃 <76> 3-Cl 5-Cl 〃 〈<77> 3-Cl 2-CH_Three, 5-Cl 〃 78 <78> 2-Br 4-Br 〃 〃 <79> 2-Br 5-CH_Three, 4-Br 〃 〃 <80> 2-F 3,4,5,6-F 〃 〈<81> 2-Cl 3,4,5,6-Cl 〃 〈<82> 2-Br 4-C_TwoH_Five 〃 〃 <83> 4-Br 3-C_ThreeH₇ 〃 〃 <84> 2-I 4-CH_Three 〃 〃 <85> 4-I 2-C_TwoH_Five 〃 〃 <86> 2-CN 4-CH_Three 〃 〃 <87> 2-CN 4-C_FourH₉ 〃 〃 <88> 3-CN 4-CH_Three 〃 〈<89> 2-Br H (n = 0) 4-Cl 〃 <90> 3-Br H (〃) 〃 〈<91> 4-Br H (〃) 〃 〈<92> 2-FH (〃 ) 〃 〃 <93> 3-FH (〃) 〃 〈<94> 4-FH (〃) 〃 〈<95> 2-IH (〃) 〃 〃 <96> 3-IH (〃) 〃 97 <97> 4-IH (〃) 〃 〈<98> 2-Cl H (〃) 〃 〈<99> 3-Cl H (〃) 〃 〃 <100> 2-CN H (〃) 〃 〈<101> 3-CN H (〃) 〃 〃 <102> 4-Cl H (〃) 4-N (C_TwoH_Five)_Two 4-CN <103> 4-Cl H (〃) 4-N (CH_Two-Ph)_Two 4-CN <104> 4-Br H (〃) 4-N (CH_Three) (CH_Two-Ph) 4-CN <105> 4-CN H (〃) 4-OC_TwoH_Five 4-CN <106> 4-CN H (〃) 2,4-di-Cl 2,4-di-Cl <107> 2-CN 4-CN 4-CN 4-CN <108> 3-Cl 2- CH_Three 4-CH_Three 4-CH_Three  <109> 3-Cl 4-CH_Three 2-CH_Three H <110> 5-Cl 2-CH_Three 3-CH_Three H <111> 2-F 5-CH_Three 4-OCH_Three 4-OCH_Three  <112> 3-F 2-CH_Three 2,4-di-CH_Three H <113> 3-F 4-CH_Three 2,5-di-CH_Three H <114> 4-F 2-CH_Three 3,4-di-CH_Three H <115> 5-F 2-CH_Three 4-CH_Three 4-CH_Three  <116> 2-Cl 4-Cl 2-CH_Three H <117> 2-Cl 3-CH_Three, 4-Cl 3-CH_Three H <118> 2-Cl 5-CH_Three, 4-Cl 2,4-di-CH_Three H <119> 2-Cl 6-CH_Three, 4-CH_Three 4-OCH_Three H <120> 3-Cl 5-Cl 2-Cl 3-Br <121> 3-Cl 2-CH_Three, 5-Cl 4-Cl H <122> 2-Br 4-Br 4-N (CH_Three) (C_TwoH_Five) H <123> 2-Br 5-CH_Three, 4-Br 4-C_ThreeH₇ H <124> 2-F 3,4,5,6-F 4-F 4-CH_Three  <125> 2-Cl 3,4,5,6-Cl 4-Br H <126> 2-Br 4-C_TwoH_Five 4-I H <127> 4-Br 4-C_ThreeH₇ 4-CN H <128> 2-I 4-CH_Three 2,4-di-Cl 2-Cl <129> 4-I 2-C_TwoH_Five 4-N (CH_Three)_Two H <130> 2-CN 4-CH_Three 2,3,4,5,6 Per-F H <131> 2-CN 4-C_FourH₉ 4-C_FourH₉ 3-CN <132> 3-CN 4-CH_Three 3-OCH_Three 3-OCH_Three  <133> 2-CF_Three H (n = 0) 4-OCH_Three H <134> 3-CF_Three H (〃) 2-C_TwoH_Five 4-CH_Three <135> 4-CF_Three H (〃) 2,4-di-CH_Three H <136> 3-CN 4-CN 2-CH_Three 3-CH_Three <137> 3-CN 5-CN 3,5-di-CH_Three H <138> 2-CN 4-CN 3,4-di-CH_Three 〃 <139> 3-Cl 4-Cl 2,4-di-CH_Three 〈<140> 2-Cl 4-Cl, 3-F 4-C_ThreeH₇ 〃 <141> 3-Br 5-Br 2-CH_Three 〃 <142> 2-Br 3-CH_Three 4-OCH_Three 〃 <143> 4-Br 2-CH_Three 3-CH_Three 3-CH_Three <144> 2-Cl 5-CH_Three 2-CH_Three 4-CH_Three <145> 2-Cl 6-CH_Three 3-CH_Three 4-CH_Three <146> 2-CN 4-CH_Three 2-CH_Three 3-CH_Three <147> 3-CN 4-CH_Three 2-CH_Three 3-CH_Three <148> 3-Cl 2-CH_Three 2-CH_Three 3-CH_Three <149> 3-Cl 4-CH_Three 4-OCH_Three H <150> 2-CN 4-CH_Three 4-N (CH_Three)_Two 〃 <151> 3-CN 4-CH_Three 4-N (CH_Three)_Two 〃 <152> 2-Cl 3-CH_Three, 4-Cl 4-CN 〃 <153> 2-CF_Three 3-CH_Three 3-CN 〈<154> 2-Br 4-CH_Three, 3-Br 4-CH_Three 〃 <155> 2-F 3-Cl 4-CH_Three 3-Br, 2-F <156> 2-CN H (n = 0) 4-CF_Three H <157> 3-Cl H (〃) 2-CF_Three 〃

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Table 44 No. R¹¹ R¹² R^13a R^13b  ─────────────────────────────────── (1) 2-OCH_Three H (n = 0) 2-OCH_Three H (2) 3-OCH_Three H (〃) 2-OCH_Three 〃 (3) 2-N (C_TwoH_Five)_Two H (〃) 2-OCH_Three 〃 (4) 3-N (C_TwoH_Five)_Two H (〃) 3-OC_TwoH_Five 〃 (5) 2-OCH_Three 3-CH_Three 4-CH_Three 〃 (6) 3-OCH_Three 2-CH_Three 〃 〃 (7) 4-OCH_Three 2-CH_Three 〃 〃 (8) 5-OCH_Three 2-CH_Three 〃 〃 (9) 6-OCH_Three 2-CH_Three 〃 〃 (10) 2-N (C_TwoH_Five)_Two 3-CH_Three 〃 〃 (11) 3-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (12) 4-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (13) 5-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (14) 6-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (15) 2-OC_TwoH_Five 3-CH_Three 〃 〃 (16) 3-OC_TwoH_Five 2-CH_Three 〃 〃 (17) 4-OC_TwoH_Five 2-CH_Three 〃 〃 (18) 5-OC_TwoH_Five 2-CH_Three 〃 〃 (19) 6-OC_TwoH_Five 2-CH_Three 〃 〃 (20) 2-OCH_Three H (n = 0) H 〃 (21) 3-OCH_Three H (〃) 〃 22 (22) 2-N (C_TwoH_Five)_Two H (〃) 〃 23 (23) 3-N (C_TwoH_Five)_Two H (〃) 〃 〃 (24) 2-OCH_Three 5-Cl 〃 〃 (25) 3-OCH_Three 4-C_TwoH_Five 〃 〃 (26) 4-OCH_Three 2-C_ThreeH₇ 〃 〃 (27) 3-OCH_Three 4-Cl 〃 〃 (28) 6-OCH_Three 2,4-di-Cl 〃 〃 (29) 2-N (C_TwoH_Five)_Two 4-C_TwoH_Five 〃 〃 (30) 3-N (C_TwoH_Five)_Two 5-CN 〃 〃 (31) 4-N (C_TwoH_Five)_Two 2-Br 〃 〃 (32) 5-N (C_TwoH_Five)_Two 3-CN 〃 〃 (33) 6-N (C_TwoH_Five)_Two 2,4-di-CH_Three 〃 34 (34) 2-OC_TwoH_Five 4-C_TwoH_Five 〃 〃 (35) 3-OC_TwoH_Five 2-C_TwoH_Five 〃 〃 (36) 4-OC_TwoH_Five 2-CN 〃 〃 (37) 5-OC_TwoH_Five 3-Br 〃 〃 (38) 6-OC_TwoH_Five 2,4-di-CH_Three 〃 39 (39) 2-OCH_Three H (n = 0) 4-N (CH_Three)_Two H (40) 3-OCH_Three H (〃) 4-N (C_TwoH_Five)_Two 〃 (41) 2-N (C_TwoH_Five)_Two H (〃) 4-OC_TwoH_Five 〃 (42) 3-N (C_TwoH_Five)_Two H (〃) 4-N (CH_Two-Ph)_Two 〃 (43) 2-OCH_Three 4-CH_Three 4-N (CH_Three) (CH_Two-Ph) 〃 (44) 3-OCH_Three 5-CH_Three 4-C_TwoH_Five 〃 (45) 4-OCH_Three 2-C_FourH₉ 4-C_TwoH_Five 〃 (46) 5-OCH_Three 3-C_TwoH_Five 4-CN 〃 (47) 2-OCH_Three 4-C_TwoH_Five 4-I 〃 (48) 2-N (C_TwoH_Five)_Two 4-C_TwoH_Five 4-C_TwoH_Five 〃 (49) 3-N (C_TwoH_Five)_Two 4-C_ThreeH₇ 4-Br 〃 (50) 4-N (C_TwoH_Five)_Two 2-C_ThreeH₇ 4-I 〃 (51) 5-N (C_TwoH_Five)_Two 3-C_TwoH_Five 4-Cl 〃 (52) 6-N (C_TwoH_Five)_Two 2,4-di-C_TwoH_Five 4-F 〃 (53) 2-OC_TwoH_Five 4,6-di-C_TwoH_Five 4-Cl 〃 (54) 3-OC_TwoH_Five 5-F 4-C_ThreeH₇ 〃 (55) 4-OC_TwoH_Five 2,6-di-CN 4-C_TwoH_Five 〃 (56) 5-OC_TwoH_Five 3-I 4-CN 〃 (57) 2-OC_TwoH_Five 4-Cl 2-CH_Three 〃 (58) 2-OCH_Three H (n = 0) 4-N (CH_Three)_Two 4-CH_Three  (59) 3-OCH_Three H (〃) 4-N (C_TwoH_Five)_Two 〃 (60) 2-N (C_TwoH_Five)_Two H (〃) 4-OC_TwoH_Five 〃 (61) 3-N (C_TwoH_Five)_Two H (〃) 4-N (CH_Two-Ph)_Two 〃 (62) 2-OCH_Three 4-CH_Three 4-N (CH_Three) (CH_Two-Ph) 〃 (63) 3-OCH_Three 5-CH_Three 4-C_TwoH_Five 〃 (64) 4-OCH_Three 2-C_FourH₉ 4-C_TwoH_Five 〃 (65) 5-OCH_Three 3-C_TwoH_Five 4-CN 〃 (66) 2-OCH_Three 4-C_TwoH_Five 4-I 〃 (67) 2-N (C_TwoH_Five)_Two 4-C_TwoH_Five 4-C_TwoH_Five 〃 (68) 3-N (C_TwoH_Five)_Two 4-C_ThreeH₇ 4-Br 〃 (69) 4-N (C_TwoH_Five)_Two 2-C_ThreeH₇ 4-I 〃 (70) 5-N (C_TwoH_Five)_Two 3-C_TwoH_Five 4-Cl 〃 (71) 6-N (C_TwoH_Five)_Two 2,4-di-C_TwoH_Five 4-F 〃 (72) 2-OC_TwoH_Five 4,6-di-C_TwoH_Five 4-Cl 〃 (73) 3-OC_TwoH_Five 5-F 4-C_ThreeH₇ 〃 (74) 4-OC_TwoH_Five 2,6-di-CN 4-C_TwoH_Five 〃 (75) 5-OC_TwoH_Five 3-I 4-CN 〃 (76) 2-OC_TwoH_Five 4-Cl 2-CH_Three 〃 (77) 2-OCH_Three H (n = 0) 4-CH_Three 2-Br (78) 3-OCH_Three H (〃) 4-CH_Three 2-C_TwoH_Five  (79) 2-N (C_TwoH_Five)_Two H (〃) 4-CH_Three H (80) 3-N (C_TwoH_Five)_Two H (〃) 2-CH_Three 4-Br (81) 2-OCH_Three 4-CH_Three 4-C_TwoH_Five 2-CN (82) 3-OCH_Three 4-C_TwoH_Five 4-Cl 2-I (83) 4-OCH_Three 2-C_ThreeH₇ 〃 H (84) 3-OCH_Three 4-Cl 〃 H (85) 6-OCH_Three 2,4-di-Cl 〃 H (86) 2-N (C_TwoH_Five)_Two 4-C_TwoH_Five 〃 4-CH_Three  (87) 3-N (C_TwoH_Five)_Two 5-CN 〃 4-CH_Three  (88) 4-N (C_TwoH_Five)_Two 2-Br 〃 H (89) 5-N (C_TwoH_Five)_Two 3-CN 〃 90 (90) 6-N (C_TwoH_Five)_Two 2,4-di-CH_Three 〃 〃 (91) 2-OC_TwoH_Five 4-C_TwoH_Five 〃 〃 (92) 3-OC_TwoH_Five 2-C_TwoH_Five 〃 〃 (93) 4-OC_TwoH_Five 2-CN 〃 94 (94) 5-OC_TwoH_Five 3-Br 〃 〃 (95) 6-OC_TwoH_Five 2,4-di-CH_Three 〃 〃 (96) 2-OCH_Three H (n = 0) 2-OCH_Three 4-N (CH_Three)_Two  (97) 3-OCH_Three H (〃) 2-OCH_Three 4-Br (98) 2-N (C_TwoH_Five)_Two H (〃) 2-OCH_Three 4-F (99) 3-N (C_TwoH_Five)_Two H (〃) 3-OC_TwoH_Five 4-Cl (100) 2-OCH_Three 3-CH_Three 4-CH_Three 2,3,4, tri-Cl (101) 3-OCH_Three 2-CH_Three 〃 2,4-di-Cl (102) 4-OCH_Three 2-CH_Three 〃 2,3,4, tri-F (103) 5-OCH_Three 2-CH_Three 〃 4-CH_Three  (104) 6-OCH_Three 2-CH_Three 〃 〃 (105) 2-N (C_TwoH_Five)_Two 3-CH_Three 〃 〃 (106) 3-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (107) 4-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (108) 5-N (C_TwoH_Five)_Two 2-CH_Three 〃 109 (109) 6-N (C_TwoH_Five)_Two 2-CH_Three 〃 〃 (110) 2-OC_TwoH_Five 3-CH_Three 〃 〃 (111) 3-OC_TwoH_Five 2-CH_Three 〃 〃 (112) 4-OC_TwoH_Five 2-CH_Three 〃 113 (113) 5-OC_TwoH_Five 2-CH_Three 〃 〃 (114) 6-OC_TwoH_Five 2-CH_Three 〃 115 (115) 2-N (CH_Three)_Two 3-CH_Three 〃 2-CH_Three  (116) 3-N (CH_Three)_Two 2-CH_Three 〃 2-CH_Three  (117) 4-N (CH_Three)_Two 2-CH_Three 〃 2-N (CH_Three)_Two  (118) 5-N (CH_Three)_Two 2-CH_Three 〃 2-CH_Three  (119) 6-N (CH_Three)_Two 2-CH_Three 〃 2-N (CH_Three)_Two  (120) 2-N (CH_Three)_Two 3-CH_Three 〃 H (121) 3-N (CH_Three)_Two 2-CH_Three 〃 〃 (122) 4-N (CH_Three)_Two 2-CH_Three 〃 〃 (123) 5-N (CH_Three)_Two 2-CH_Three 〃 124 (124) 6-N (CH_Three)_Two 2-CH_Three 〃 〃 (125) 2-N (CH_Three)_Two H (n = 0) H 〃 (126) 2-N (CH_Three)_Two H (n = 0) 4-CH_Three 〃 (127) 2-OCH_Three 4-OCH_Three H 〃 (128) 3-N (CH_Three)_Two H (n = 0) 4-CH_Three 〃 (129) 3-OCH_Three 4-OCH_Three H 〃 (130) 4-N (CH_Three)_Two H (n = 0) 4-CH_Three 〃 (131) 4-OC_TwoH_Five H (〃) 4-CH_Three 〃 (132) 4-OC_TwoH_Five H (〃) 3-CH_Three 〃 (133) 4-OC_TwoH_Five H (〃) 2-CH_Three 〃 (134) 2-OC_TwoH_Five H (〃) 4-CH_Three 〃 (135) 2-OCH_Three 5-OCH_Three H 〃 (136) 4-N (CH_Three)_Two H (n = 0) 4-Cl 〃 (137) 4-N (CH_Three)_Two H (n = 0) 4-Br 〃 (138) 2-N (CH_Three)_Two 4-N (CH_Three)_Two H 〃 (139) 4-N (CH_Three)_Two H (n = 0) 2,4-di-Cl 〃 (140) 〃 〃 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (141) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (142) 〃 〃 H 4-N (C_TwoH_Five)_Two (143) 〃 〃 〃 3-N (C_TwoH_Five)_Two (144) 〃 〃 〃 2-N (C_TwoH_Five)_Two (145) 〃 〃 4-OCH_Three 4-OCH_Three  (146) 〃 〃 H 4-OCH_Three  (147) 〃 〃 〃 2-CH_Three  (148) 〃 〃 〃 3-CH_Three  (149) 〃 〃 〃 H (150) 3-N (C_TwoH_Five)_Two 〃 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (151) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (152) 〃 〃 H 4-N (C_TwoH_Five)_Two (153) 〃 〃 〃 3-N (C_TwoH_Five)_Two (154) 〃 〃 〃 2-N (C_TwoH_Five)_Two (155) 〃 〃 4-OCH_Three 4-OCH_Three  (156) 〃 〃 H 4-OCH_Three  (157) 〃 〃 〃 2-CH_Three  (158) 〃 〃 〃 3-CH_Three  (159) 〃 〃 〃 4-CH_Three  (160) 〃 〃 〃 4-Cl (161) 2-N (C_TwoH_Five)_Two 〃 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (162) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (163) 〃 〃 H 4-N (C_TwoH_Five)_Two (164) 〃 〃 〃 3-N (C_TwoH_Five)_Two (165) 〃 〃 〃 2-N (C_TwoH_Five)_Two (166) 〃 〃 4-OCH_Three 4-OCH_Three  (167) 〃 〃 H 2-CH_Three  (168) 〃 〃 〃 3-CH_Three  (169) 〃 〃 〃 4-Cl (170) 3-OCH_Three 4,5-OCH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (171) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (172) 〃 〃 H 4-N (C_TwoH_Five)_Two (173) 〃 〃 〃 3-N (C_TwoH_Five)_Two (174) 〃 〃 〃 2-N (C_TwoH_Five)_Two (175) 〃 〃 4-OCH_Three 4-OCH_Three  (176) 〃 〃 H 4-OCH_Three  (177) 〃 〃 〃 2-CH_Three  (178) 〃 〃 〃 3-CH_Three  (179) 〃 〃 〃 4-CH_Three  (180) 〃 〃 〃 H (181) 〃 〃 〃 4-Cl (182) 2-OCH_Three 4-OCH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (183) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (184) 〃 〃 H 4-N (C_TwoH_Five)_Two (185) 〃 〃 〃 3-N (C_TwoH_Five)_Two (186) 〃 〃 〃 2-N (C_TwoH_Five)_Two (187) 〃 〃 4-OCH_Three 4-OCH_Three  (188) 〃 〃 H 4-OCH_Three  (189) 〃 〃 〃 2-CH_Three  (190) 〃 〃 〃 3-CH_Three  (191) 〃 〃 〃 4-CH_Three  (192) 〃 〃 〃 4-Cl (193) 〃 5-OCH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (194) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (195) 〃 〃 H 4-N (C_TwoH_Five)_Two (196) 〃 〃 〃 3-N (C_TwoH_Five)_Two (197) 〃 〃 〃 2-N (C_TwoH_Five)_Two (198) 〃 〃 4-OCH_Three 4-OCH_Three  (199) 〃 〃 H 4-OCH_Three  (200) 〃 〃 〃 2-CH_Three  (201) 〃 〃 〃 3-CH_Three  (202) 〃 〃 〃 4-CH_Three  (203) 〃 〃 〃 4-Cl (204) 3-OCH_Three 4-OCH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (205) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (206) 〃 〃 H 4-N (C_TwoH_Five)_Two (207) 〃 〃 〃 3-N (C_TwoH_Five)_Two (208) 〃 〃 〃 2-N (C_TwoH_Five)_Two (209) 〃 〃 4-OCH_Three 4-OCH_Three  (210) 〃 〃 H 4-OCH_Three  (211) 〃 〃 〃 2-CH_Three  (212) 〃 〃 〃 3-CH_Three  (213) 〃 〃 〃 4-CH_Three  (214) 〃 〃 〃 4-Cl (215) 2-OCH_Three 5-CH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (216) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (217) 〃 〃 H 4-N (C_TwoH_Five)_Two (218) 〃 〃 〃 3-N (C_TwoH_Five)_Two (219) 〃 〃 〃 2-N (C_TwoH_Five)_Two (220) 〃 〃 4-OCH_Three 4-OCH_Three  (221) 〃 〃 H 4-OCH_Three  (222) 〃 〃 〃 2-CH_Three  (223) 〃 〃 〃 3-CH_Three  (224) 〃 〃 〃 4-CH_Three  (225) 〃 〃 〃 H (226) 〃 〃 〃 4-Cl (227) 2-OCH_Three 6-CH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (228) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (229) 〃 〃 H 4-N (C_TwoH_Five)_Two (230) 〃 〃 〃 3-N (C_TwoH_Five)_Two (231) 〃 〃 〃 2-N (C_TwoH_Five)_Two (232) 〃 〃 4-OCH_Three 4-OCH_Three  (233) 〃 〃 H 4-OCH_Three  (234) 〃 〃 〃 2-CH_Three  (235) 〃 〃 〃 3-CH_Three  (236) 〃 〃 〃 H (237) 〃 〃 〃 4-Cl (238) 4-OCH_Three 2-CH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (239) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (240) 〃 〃 H 4-N (C_TwoH_Five)_Two (241) 〃 〃 〃 3-N (C_TwoH_Five)_Two (242) 〃 〃 〃 2-N (C_TwoH_Five)_Two (243) 〃 〃 4-OCH_Three 4-OCH_Three  (244) 〃 〃 H 4-OCH_Three  (245) 〃 〃 〃 2-CH_Three  (246) 〃 〃 〃 3-CH_Three  (247) 〃 〃 〃 H (248) 〃 〃 〃 4-Cl (249) 5-OCH_Three 2-CH_Three 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (250) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (251) 〃 〃 H 4-N (C_TwoH_Five)_Two (252) 〃 〃 〃 3-N (C_TwoH_Five)_Two (253) 〃 〃 〃 2-N (C_TwoH_Five)_Two (254) 〃 〃 4-OCH_Three 4-OCH_Three  (255) 〃 〃 H 4-OCH_Three  (256) 〃 〃 〃 2-CH_Three  (257) 〃 〃 〃 3-CH_Three  (258) 〃 〃 〃 H (259) 〃 〃 〃 4-Cl (260) 3-OCH_Three H (n = 0) 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (261) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (262) 〃 〃 〃 3-N (C_TwoH_Five)_Two (263) 〃 〃 〃 2-N (C_TwoH_Five)_Two (264) 〃 〃 4-OCH_Three 4-OCH_Three  (265) 〃 〃 H 4-OCH_Three  (266) 〃 〃 〃 2-CH_Three  (267) 〃 〃 〃 3-CH_Three  (268) 〃 〃 〃 4-CH_Three  (269) 〃 〃 〃 4-Cl (270) 2-OCH_Three 〃 4-N (C_TwoH_Five)_Two 4-N (C_TwoH_Five)_Two (271) 〃 〃 4-N (CH_Three)_Two 4-N (CH_Three)_Two  (272) 〃 〃 〃 3-N (C_TwoH_Five)_Two (273) 〃 〃 〃 2-N (C_TwoH_Five)_Two (274) 〃 〃 4-OCH_Three 4-OCH_Three  (275) 〃 〃 H 4-OCH_Three  (276) 〃 〃 〃 2-CH_Three  (277) 〃 〃 〃 3-CH_Three  (278) 〃 〃 〃 4-CH_Three  (279) 〃 〃 〃 4-Cl

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[Brief description of the drawings]

FIG. 1 is an IR spectrum of an example of a carrier transporting substance based on the present invention.

FIG. 2 is an IR spectrum of an example of a carrier transporting substance according to the present invention.

FIG. 3 is a cross-sectional view of an example of an electrophotographic photosensitive member according to the present invention.

FIG. 4 is a cross-sectional view of another example of the electrophotographic photosensitive member according to the present invention.

FIG. 5 is a cross-sectional view of another example of the electrophotographic photosensitive member based on the present invention.

FIG. 6 is a cross-sectional view of another example of the electrophotographic photosensitive member according to the present invention.

FIG. 7 is a cross-sectional view of another example of the electrophotographic photosensitive member based on the present invention.

FIG. 8 is a sectional view of another example of the electrophotographic photosensitive member according to the present invention.

[Explanation of symbols]

DESCRIPTION OF SYMBOLS 1 Support 2 Carrier generating layer 3 Carrier transport layer 5 Intermediate layer 6 Layer containing a carrier generating substance and a carrier transporting substance

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor, Osamu Sasaki 1 at Sakura-cho, Hino-shi, Tokyo Inside Konica Corporation (72) Inventor Shinichi Suzuki 1 at Sakura-cho, Hino-shi, Tokyo Inside Konica Corporation (72) Inventor Hirofumi Hayata 1 Sakura-cho, Hino-shi, Tokyo Konica Corporation (58) Field surveyed (Int.Cl. ⁶ , DB name) G03G 5/06 313 CAPLUS (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] 1. A bisstyryl compound represented by the following general formula [I]. Embedded image [However, n = 0 or n> 1. When n = 0, R ¹
Is a chlorine atom or a cyano group substituted at 2- or 3-position with respect to the substituted amino group, or a fluorine atom, bromine atom, iodine atom or halogenated alkyl group substituted at 2- to 4-position And when n> 1, R ¹ is a halogen atom, a cyano group or a halogenated alkyl group having 1 to 4 carbon atoms, which is substituted at 2- to 4-position to the substituted amino group. R ² may be different from each other and is a substituent selected from a halogen atom, a cyano group, an alkyl group having 1 to 4 carbon atoms and a halogenated alkyl group having 1 to 4 carbon atoms. Ar ¹ and Ar ² may be different from each other; Is an aryl group represented by ｛However, x ≧ 0, y ≧
0, z ≧ 0, and when x, y, z is 2 or more, a plurality of R ³ , R ⁴ , and R ⁵ may be different from each other, and may be a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, Group,
An aralkyl group, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, (However, R ⁶ and R ⁷ may be different from each other and are an alkyl group or an aralkyl group having 1 to 4 carbon atoms.) And -OR ⁸ (where R ⁸ is a group having 1 to 4 carbon atoms). An alkyl group). ｝) 2. A bisstyryl compound represented by the following general formula [II]. Embedded image [However, n = 0 or n> 1. When n = 0, R ¹¹
Is a methoxy or diethylamino group substituted at the 2- or 3-position with respect to the substituted amino group, or
An ethoxy group or a dimethylamino group substituted at the -position, and when n> 1, R ¹¹ represents a methoxy group, an ethoxy group, a dimethylamino group substituted at the 2- to 4-position relative to the substituted amino group Or a diethylamino group. R
¹² may be different from each other and is a substituent selected from a halogen atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, a dimethylamino group and a diethylamino group. Ar ³ and Ar ⁴ may be different from each other; Is an aryl group represented by ｛However, x ≧ 0, y ≧
0, z ≧ 0, and when x, y, z is 2 or more, a plurality of R ¹³ , R ¹⁴ , and R ¹⁵ may be different from each other, and may be a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, A phenyl group, an aralkyl group, an alkyl group having 1 to 4 carbon atoms, (However, R ¹⁶ and R ¹⁷ may be different from each other and are an alkyl group or an aralkyl group having 1 to 4 carbon atoms.), -OR ¹⁸ (where R ¹⁸ is a group having 1 to 4 carbon atoms) An alkyl group), -R ¹⁹ COOR ²⁰ (where R ¹⁹ is an alkylene group having 1 to 4 carbon atoms and R ²⁰ is an alkyl group) and a substituent selected from -R ¹⁹ OCOR ²⁰ It is. ｝ However, the following compounds are excluded. Embedded image (Here, a plurality of R ²¹ and R ²² may be different from each other and are an alkyl group having 1 to 4 carbon atoms. Further, r ≧ 2 and t ≧ 0.)] 3. An electrophotographic photosensitive member containing the bisstyryl compound represented by the general formula [I] according to claim 1. 4. An electrophotographic photosensitive member containing the bisstyryl compound represented by the general formula [II] according to claim 2.