JP3451278B2 - 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 an electrophotographic photosensitive member.
In particular, the photosensitive layer contains a specific photoconductive material
The present invention relates to a photoconductor for electrophotography. [0002] 2. Description of the Related Art Conventionally used in an electrophotographic system.
Materials used as photoconductive materials for photoreceptors
Inorganic substances such as ren, cadmium sulfide, and zinc oxide
You. As used herein, the term “electrophotographic method” generally refers to photoconductive
First, charge the photoreceptor in a dark place, for example, by corona discharge
Then, image exposure is performed to selectively charge only the exposed portions.
The latent image is erased to obtain an electrostatic latent image.
Consists of any colorants and binders such as polymeric substances
Develop with visualization particles (toner) and visualize to form an image
This is one of the image forming methods. Such an electron
Basic characteristics required for photoreceptors in photographic methods
Is that (1) it can be charged to an appropriate potential in a dark place, (2)
(3) Light irradiation
And quickly erase the charge
It is. [0003] By the way, each of the aforementioned inorganic substances is
It has many advantages, but also various disadvantages
That is the fact. For example, currently widely used
Selenium sufficiently satisfies the above conditions (1) to (3).
But difficult to manufacture, sensitive to heat and mechanical shock
Therefore, it has drawbacks such as requiring careful handling. Ma
In addition, cadmium sulfide and zinc oxide are used as resin binders.
Used as a photoreceptor.
Mechanical defects such as strength, tensile strength and friction resistance.
It cannot be used repeatedly as it is. In recent years, the disadvantages of these inorganic substances have been eliminated.
Using photoconductive materials composed of various organic substances
Photoreceptors have been proposed and some have been put to practical use.
You. For example, poly-N-vinylcarbazole and 2,4
Photoreceptor comprising 7-trinitrofluoren-9-one
(U.S. Pat. No. 3,484,237), poly-N
-Synthesize vinyl carbazole with pyrylium salt dye
Photoreceptor (described in JP-B-48-25658),
Photoreceptor containing an organic pigment as a main component (Japanese Patent Laid-Open No. 47-3754)
No. 3), eutectic complexes comprising dyes and resins
Photoreceptor as a component (described in JP-A-47-10735)
), Dye sensitization of triphenylamine compound
Light bodies (U.S. Pat. No. 3,180,730);
Photoconductor using an electron derivative as a charge transporting material (JP-A-5
7-195254), poly-N-vinyl carbazo
Using photocatalysts and amine derivatives as charge transport materials
(Described in JP-A-58-1155), polyfunctional third amine
Min compounds, especially benzidine compounds, as photoconductive materials
Photoconductor (US Pat. No. 3,265,496)
JP-B-39-11546, JP-A-53-2
No. 7033). [0005] These photosensitive members are excellent.
It seems to have high practical value
However, in electrophotography, various
These requirements are still fully satisfied
That is not to say. The present invention relates to the conventional
Eliminating the disadvantages of photoconductive materials
Providing electrophotographic photoconductors that can fully satisfy the required conditions
In addition to excellent sensitivity and cost
To obtain an electrophotographic photoreceptor that can be manufactured
aimed to. [0006] According to the present invention,below
The invention is providedYou. On a conductive support, the following general formula (I)
At least one of the diamine compounds represented by
Characterized by providing a photosensitive layer containing as a conductive material
Photoconductor for electrophotography. Embedded image (Where R¹, R^TwoAnd R^ThreeIs a hydrogen atom,
Is an unsubstituted alkyl group, substituted or unsubstituted aryl
Group or acetyl group.
You may. Ar¹Is a substituted or unsubstituted arylene group
And Ar^TwoIs a substituted or unsubstituted aromatic carbonized
Represents a trivalent group of hydrogen. Also, R¹And R^TwoOr R¹When
Ar¹May form a ring together with N. X is a substitution
Or unsubstituted alkylene group, substituted or unsubstituted
Represents a cycloalkylidene group. N is 1 or
Represents an integer of 2. ) The compound represented by the above general formula (I) is
For example, the following general formula (II) Embedded image           R¹-Y and R^Two−Y …… (II) 中 In the formula (II), R¹And R^TwoIs the same as above, Y is iodine
Represents a bromine atom. With a halide represented by｝
The following general formula (III) Embedded image 中 In the formula (III), R^Three, Ar¹, Ar^TwoAnd X are the same as above
Same. The aniline compound represented by｝
Manufactured by Ullmann reaction
You. A diamine represented by the following general formula (I)
The compound will be described in more detail. Represented by the general formula (I)
In the diamine compound represented by¹~ R^Three, Ar¹~ A
r^Two, X and Y, or a substituent thereof
The following can be mentioned. (1) Hydrogen atom (-H) (2) Halogen atom (-X): fluorine, chlorine, bromine, iodine
Element atoms. (3) cyano group (-CN) (4) Nitro group (-NO_Two) (5) Hydroxy group (-OH) (6) alkyl group (-R^Four), C₁~ C₁₂And especially C₁
~ C₉And more preferably C₁~ C_FourStraight or branched chain of
Alkyl groups.
Elemental atom, hydroxyl group, cyano group, C₁~ C_FourAn alkoxy group of
Phenyl group or halogen atom, C₁~ C_FourAlkyl group
Or C₁~ C_FourPhenyl substituted with an alkoxy group
May contain a hydroxyl group. Specifically, methyl, ethyl
Group, n-propyl group, i-propyl group, t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoro
Oromethyl group, 2-phenylethyl group, 2-hydroxy
Ethyl group, 2-cyanoethyl group, 2-ethoxyethyl
Group, 2-methoxyethyl group, benzyl group, 4-chlorobe
Benzyl group, 4-methylbenzyl group, 4-methoxybenzyl
And a 4-phenylbenzyl group. (7) alkoxy group (-OR^Four): R^FourIs defined in (6)
Represents an alkyl group. Specifically, methoxy group, eth
Xy group, n-propoxy group, i-propoxy group, t-butyl
Toxyl group, n-butoxy group, s-butoxy group, i-butoxy
Xy group, 2-hydroxyethoxy group, 2-cyanoethoxy
Si group, benzyloxy group, 4-methylbenzyloxy
Group, trifluoromethoxy group and the like. (8) alkylthio group (-SR^Four): R^FourIs defined in (6)
Represents an alkyl group. Specifically, a methylthio group,
Ethylthio group, benzylthio group, hydroxyethylthio
And the like. (9) an alkylene group (-R^Five-): -R^Five-Is determined in (6)
Represents a divalent group derived from the defined alkyl group. Concrete
Methylene group, ethylene group, 1,3-propylene
Group, 1,4-butylene group, 2-methyl-1,3-propyl
Len group, difluoromethylene group, hydroxyethylene
Group, cyanoethylene group, methoxyethylene group, phenyl
Methylene group, 4-methylphenylmethylene group, 2,2-
Propylene group, 2,2-butylene group, diphenylmethylene
And the like. (10) Dialkylene ether group (-R⁶-OR
⁷-): R⁶, R⁷Represents an alkylene group defined in (9)
I forgot. Specifically, dimethylene ether group, diethylene ether
-Ter group, methylene, ethylene ether group, etc.
You. (11) cycloalkylidene group ｛represented by the following general formula (IV)
Basics: Embedded image Specifically, a 1,1-cyclopentylidene group,
A cyclohexylidene group or a 1,1-cyclooctylidene group
Can be mentioned. (12) Aryl group (-Ar^Three): Carbocyclic aromatic group also
Or a heterocyclic aromatic group.
Group, biphenyl group, terphenyl group, pentalenyl
Group, indenyl group, naphthyl group, azulenyl group, hepta
A phenyl group, a biphenylenyl group, an as-indacenyl group,
Fluorenyl group, s-indacenyl group, acenaphthyleni
Group, preadenyl group, acenaphthenyl group, phenale
Nil group, phenanthryl group, anthryl group, fluoran
Thenyl group, acephenanthrenyl group, aceanthryl
Nil, triphenylenyl, pyrenyl, chryseni
, Naphthacenyl, pyridyl, pyrimidyl
Group, pyrazinyl group, triazinyl group, furyl group, pyrrolyl
, Thienyl, quinolyl, coumarinyl, benzo
Furanyl group, benzimidazolyl group, benzoxazolyl
Group, dibenzofuranyl group, benzothienyl group, diben
Zothionyl group, indolyl group, carbazolyl group, pyrazo
Ryl group, imidazolyl group, oxazolyl group, isoxa
Zolyl, thiazolyl, indazolyl, benzothia
Zolyl, pyridazinyl, cinnolinyl, quinazolyl
Nil group, quinoxalyl group, phthalazinyl group, phthalazine
Dionyl group, chromonyl group, naphtholactonyl group, quino
Ronyl group, imidyl group of o-sulfobenzoate, maleic acid
Imidyl group, naphthalidinyl group, benzimidazolonyl
Group, benzoxazolonyl group, benzothiazolonyl group,
Benzothiazothionyl group, quinazolonyl group, quinoxalo
Group, phthalazonyl group, dioxopyrimidinyl group,
Lidonyl group, isoquinolonyl group, isoquinolyl group, iso
Thiazolyl group, benzisoxazolyl group, benziso
Thiazolyl, indazolonyl, acridinyl, a
Clidonyl group, quinazolindionyl group, quinoxaringi
Onyl group, benzoxazinedionyl group, benzoxa
Dinyl group and naphthalimidyl group are exemplified. Also,
These aryl groups have the substituents shown in (2) to (8).
You may. (13) aryloxy group (—OAr^Three): Ar^ThreeIs (1
Represents an aryl group defined in 2). Specifically, Feno
Xy, 4-methylphenoxy, naphthoxy and the like.
I can do it. (14) arylthio group (—SAr^Three): Ar^ThreeIs (1
Represents an aryl group defined in 2). Specifically, Pheni
And a luthio group and a naphthylthio group. (15) Arylene group (-Ar^Four-): -Ar^Four-Is (1
Represents a divalent group derived from the aryl group defined in 2)
You. Specifically, phenylene group, biphenylylene group, pyre
Nirylene group, N-ethylcarbazolylene group, etc.
Can be. (16) amino group ｛-N (R⁸) (R⁹)｝: R⁸, R⁹Is
Each independently a hydrogen atom, an alkyl group defined in (6),
Represents the aryl group defined in (12), and forms a ring together
May be implemented. Specifically, amino group, diethylamino
Group, N-methyl-N-phenylamino group, N, N-diff
Phenylamino group, N, N-di (p-tolyl) amino
Group, dibenzylamino group, piberidino group, morpholino
And a urolidyl group. (17) vinyl group ｛the following general formula (V) or general formula
Group represented by (VI) Embedded image 中 where R^Ten, R¹¹Are (1)-(5), (12)-(1
4) In R¹², R¹³Is determined by (9), (10) and (15)
J represents an integer of 0 or 1;
Is an oxygen atom, a sulfur atom, a vinylene group or an alkylene
Represents a group. ｝ Specifically, a styryl group, 4-methyls
Tyryl group, β-methylstyryl group, 4-chlorostyryl
Group, β-phenylstyryl group, β- (4-methylphenyl
L) styryl group, 4-phenyl-1,3-butadienyl
And the like. The following are alternatives to the diamine compound used in the present invention.
In order to avoid complications in tabular examples, the chemical structural formulas
Table 1-1 to Table 1-5
It shows in -1 to 2-4. Thereafter, the diamine compound No. Haso
No. of each table. It is expressed by a combination of Example: Diamine compound No. 2-18 Embedded image [0010] [Table 1- (1)][0011] [Table 1- (2)][0012] [Table 1- (3)][0013] [Table 1- (4)][0014] [Table 1- (5)][0015] [Table 2- (1)][0016] [Table 2- (2)][0017] [Table 2- (3)][0018] [Table 2- (4)]The photoreceptor using the photoconductive material of the present invention comprises:
Contains one or more of the above diamine compounds
The photosensitive layer 2 (2 ′, 2 ″, 2 ′ ″ or
2 '' '')
Figure depending on how to apply photoconductive material containing compound
1, 2, 3, 4 or 5
Can be The photosensitive member in FIG. 1 is placed on a conductive support 1.
Diamine compound, sensitizing dye and binder (binder resin)
The photosensitive layer 2 is provided. Zia here
Min compounds act as photoconductive substances and are required for light attenuation
The generation and transfer of the various charge carriers are via the diamine compound.
It is done. However, the diamine compound does not
Possible because it has almost no absorption in the visible region
Absorption in the visible region for the purpose of forming images with visual light
It is necessary to sensitize by adding the sensitizing dye having the sensitizing dye. The photosensitive member shown in FIG.
The charge generating substance 3 comprises a diamine compound and a binder
The photosensitive layer 2 'dispersed in the charge transport medium 4 is provided.
It was a thing. The diamine compound here is a binder
(Or charge carrier with binder and plasticizer)
While the charge generating substance 3 (inorganic or organic pigment
Charge-generating substances) generate charge carriers. This place
In this case, the charge transport medium 4 mainly generates the charge generating substance 3.
In charge of receiving charge carriers and transporting them.
You. In this photoreceptor, the charge generating substance and
Min compounds absorb each other, mainly in the visible region.
The basic condition is that the collection wavelength regions do not overlap.
This allows the charge generation material 3 to efficiently generate charge carriers.
Must transmit light to the surface of the charge generating material
Because there is. The photosensitive member shown in FIG.
A charge generation layer 5 mainly composed of a charge generation substance 3;
Consisting of a laminate with a charge transport layer 4 containing a compound
A layer 2 '' is provided. In this photoreceptor,
The light transmitted through the load transport layer 4 reaches the charge generation layer 5 and
The generation of charge carriers occurs in the region, while the charge transport layer 4
It receives charge carriers and transports them.
The generation of charge carriers required for decay is performed by the charge generating substance 3.
The charge carrier is transported by the charge transport layer 4 (mainly
The diamine compound works). Such a mechanism
Is the same as that described for the photoconductor shown in FIG. The photosensitive member in FIG.
And stacking order of the charge transport layer 4 containing the diamine compound
And a device for generating and transporting the charge carriers.
The structure can be the same as described above. In this case, the mechanical strength
Considering this, a protective layer 6 is formed on the charge generation layer 5 as shown in FIG.
It can also be provided. Actually, photosensitive using the photoconductive material of the present invention.
To manufacture the body, if the photoconductor shown in FIG.
One or more diamine compounds are added to the solution in which the agent is dissolved.
Dissolve the top and add a sensitizing dye to this solution
This is coated on a conductive support 1 and dried to form a photosensitive layer 2
May be formed. The thickness of the photosensitive layer is preferably 3 to 50 μm.
More preferably, it is 5 to 20 μm. Occupy in the photosensitive layer 2
The amount of the dorazone compound is 30-70% by weight, preferably about
50% by weight, and the sensitizing dye
The amount is 0.1-5% by weight, preferably 0.5-3% by weight
is there. As sensitizing charges, brilliant green, big
Tria blue B, methyl violet, crystal by
Triettes such as Olet and Acid Violet 6B
Methane dye, rhodamine B, rhodamine 6G, raw
Damin G Extra, Eosin S, Erythrosin, Rho
Xenthene dyes, such as svengal, fluorescein,
Thiazine dyes like methylene blue, like cyanine
Cyanine dye, 2,6-diphenyl-4- (N, N-
Dimethylaminophenyl) thiapyrylium perchlore
Benzopyrylium salt (JP-B-48-25658)
Pyrylium dyes, etc.). What
Even if these sensitizing infections are used alone, two or more
May be used. Further, in manufacturing the photoreceptor shown in FIG.
Comprises one or more diamine compounds and a binder
Disperse the fine particles of the charge generating substance 3 in the dissolved solution,
This is coated on a conductive support 1 and dried to form a photosensitive layer 2 '.
It may be formed. The thickness of the photosensitive layer 2 ′ is 3 to 50 μm,
Preferably, 5 to 20 μm is appropriate. Occupy photosensitive layer 2 '
The amount of the diamine compound is 10 to 95% by weight, preferably
30 to 90% by weight, and the charge occupying the photosensitive layer 2 '.
The amount of the load generating substance 3 is 0.1 to 50% by weight, preferably 1%.
-20% by weight. As the charge generating material 3, for example, selenium,
Selenium-tellurium, cadmium sulfide, cadmium sulfide-ce
Inorganic pigments such as len, α-silicon, and organic pigments
For example, CI Pigment Blue 25 (color index)
Cs CI 21180), CI Pigment Red 4
1 (CI 21200), CI Acid Red 52
(CI 45100), sea eye basic red 3
(CI 45210), azo having a carbazole skeleton
Pigments (described in JP-A-53-95033), dist
Azo pigments having a benzene skeleton (JP-A-53-13)
No. 3445), a compound having a triphenylamine skeleton.
Azo pigments (described in JP-A-53-132347),
Azo pigments having a benzothiophene skeleton (Japanese Unexamined Patent Publication No.
21728), having an oxadiazole skeleton.
Azo pigments (described in JP-A-54-12742).
Azo pigments having a fluorenone skeleton (JP-A-54
No. 22834), having a bisstilbene skeleton
Azo pigments (described in JP-A-54-17733).
Azo face with distyryl oxadiazole skeleton
(Described in JP-A-54-2129), distyryl
Azo pigments having a carbazole skeleton (JP-A-54-14)
Azo pigments such as C.I.
Pigment Blue 16 (CI 74100)
Russiannin pigments, for example, Sea Ivat Brown 5
(CI73410), sea butt die (CI73
030) and other indigo pigments, Argo Scarlet B
(Manufactured by Bayer AG), Indance Scarlet R (bath)
Perylene-based pigments and the like.
In addition, even if these charge generating substances are used alone,
The above may be used in combination. Further, in manufacturing the photosensitive member shown in FIG.
Vacuum-deposits a charge generating substance on the conductive support 1
Or, if necessary, fine particles 3 of a charge generating substance.
Applying a dispersion dispersed in a suitable solvent with the binder dissolved
Or dry, and if necessary, buffing
Charge generation by surface finishing, film thickness adjustment, etc.
A raw layer 5 is formed on which one or more diamines are formed.
Apply a solution in which the binder compound and binder are dissolved, dry and apply
The load transport layer 4 may be formed. Here, the charge generation layer
The charge generating substance used for forming the photosensitive layer 5 is the photosensitive layer 2 'described above.
Are the same as those described in the description. Charge generation layer
5 has a thickness of 5 μm or less, preferably 2 μm or less;
The thickness of the charge transport layer 4 is 3 to 50 μm, preferably 5 to 50 μm.
20 μm is appropriate. The charge generation layer 5 is
Of a type in which fine particles 3 are dispersed in a binder.
Is the ratio of the fine particles 3 of the charge generating substance to the charge generating layer 5.
10 to 95% by weight, preferably about 50 to 90% by weight
And the amount of the compound in the charge transport layer 4 is 1%.
It is 0 to 95% by weight, preferably 30 to 90% by weight. To manufacture the photoreceptor shown in FIG.
Dissolving a diamine compound and a binder on a porous support 1
After applying the liquid and drying to form the charge transport layer 4,
Fine particles of the charge generating substance on the charge transport layer
Spray the dispersion dispersed in the solvent in which the binder was dissolved.
-Forming the charge generating layer 5 by coating and drying by a method such as coating
I just need. The quantity ratio of the charge generation layer or the charge transport layer is shown in FIG.
This is the same as the content described. The feeling obtained in this way
Spray an appropriate resin solution on the charge generation layer 5 of the photoreceptor.
By forming the protective layer 6 by a method such as laye coating,
The photoconductor shown in FIG. 5 can be manufactured. The resin used here
Alternatively, the binder described below can be used. Incidentally, in the production of these photoconductors,
A metal plate such as aluminum or a metal
Foil, plastic foil on which metal such as aluminum is deposited
Film or paper with conductive treatment
You. In addition, as the binder, polyamide, polyurethane,
Polyester, epoxy resin, polyketone, polycarbonate
Condensation resins such as polycarbonate, polyvinyl ketone, poly
Styrene, poly-N-vinyl carbazole, polyacryl
Although vinyl polymers such as luamide are used,
Any resin having an edge and having an adhesive property can be used.
Plasticizers may be added to the binder if necessary.
Halogenated paraffin, polychlorinated biphenyl
Dimethyl naphthalene, dibutyl phthalate, etc.
Can be shown. Further, the photoreceptor obtained as described above
The conductive support and the photosensitive layer, if necessary.
A deposition or barrier layer can be provided. These layers
Polyamide, nitrocellulose
And aluminum oxide, and the film thickness is 1 μm
The following is preferred. When making a copy using the photoreceptor of the present invention
After the photoreceptor surface is charged and exposed, development is performed.
If necessary, transfer to paper. The feeling of the present invention
Light body has excellent advantages such as high sensitivity and high flexibility
have. [0032] The present invention will be described below with reference to examples. What
In the following examples, all parts are parts by weight. [Synthesis Example] 1,1-bis [3- (4-amido)
Nophenethyl) -4-methoxyphenyl] cyclohexa
4.84 g (9.05 mmol) of p-iodotoluene
25.42 g (108.6 mmol), potassium carbonate
10.00 g and copper powder 0.58 g were stirred under reflux in a nitrogen stream.
For 12 hours. After cooling to room temperature, celite
Then, chloroform was added to the filtrate, and the organic layer was separated.
Wash with a funnel and then dry over magnesium sulfate.
Drying and further concentration under reduced pressure gave a brown oil. This
This was treated with a silica gel column [eluent: toluene / n-
Xan = 1 / 1vol], and the resulting oil is
Crystallized, and a colorless dia represented by the following formula (VI):
Min compound [Compound No. 5.18 g (2-18)
69.5%). [0034] Embedded image Elemental analysis value is C₆₄H₆₆N_TwoO_TwoAs below
Was. Example 1 Diane was used as the charge generating material.
Blue (Sea Pigment Blue 25, CI2118
0) 76 parts, polyester resin (manufactured by Toyobo, Byron
200) in 1260 parts of a 2% tetrahydrofuran solution and
And 3700 parts of tetrahydrofuran in a ball mill
After mixing, the resulting dispersion was
On the aluminum surface of a conductive support made of steal base
Apply using a doctor blade, air dry and thickness
A charge generation layer of about 1 μm was formed. On the other hand, the charge transport material
As compound No. 1 part of the diamine compound of 2-21,
Recarbonate resin (manufactured by Teijin Limited, Panlite K130
0) 1 part and 8 parts of tetrahydrofuran are mixed and dissolved
After the solution was formed, it was doctor-brushed on the charge generation layer.
Coating at 80 ° C. for 2 minutes, then 120 ° C.
Dry at 5 ° C for 5 minutes to form a charge transport layer with a thickness of about 20 µm
At least, the photoconductor No. 1 was produced. [Examples 2 to 21]
Changed the transport material (diamine compound) to that shown in Table 3.
Except for the photoreceptor No. Two
21 was produced. [0037] [Table 3-1] [0038] [Table 3-2][0039] [Table 3-3]Example 22 Aluminum having a thickness of about 300 μm
Selenium is vacuum-deposited to a thickness of about 1 μm on
A generating layer was formed. Next, No. 2-21 diami
Compound 2 parts, polyester resin (Polyester manufactured by DuPont)
Stel, Adhesive 49000) 3 parts and Tetrahi
Mix and dissolve 45 parts of drofuran to form a charge transport layer forming liquid.
On the charge generation layer (selenium deposition layer).
Apply using a collector blade, air dry, and
Dry underneath to form a charge transport layer about 10 μm thick
The photosensitive member No. of the present invention 22 was obtained. Example 23 The following structural formula was used instead of selenium.
Perylene pigment represented by (VII) Embedded image To form a charge generation layer (however, the thickness is about 0.6 μm)
And no. 2-21 diami
Exactly as in Example 22 except that
And the photosensitive member No. No. 23 was produced. Example 24 Diane Blue (Example 1)
158
After pulverizing and mixing the mixture in a ball mill,
No. 12-21 parts of diamine compound, polyether
Stell resin (Dupont polyester, Adhesive
49000) 18 parts were added, and the mixture was further mixed.
Layer forming solution on aluminum evaporated polyester film
To the surface using a doctor blade, at 100 ° C for 30 minutes
Dried to form a photosensitive layer with a thickness of about 16 μm.
In the photoconductor No. of the invention, 24 were created. Embodiment 25 Aluminum deposited poly
Charge transport used in Example 1 on an ester film substrate
The layer coating solution was blade-coated in the same manner as in Example 1, and then
To form a charge transport layer having a thickness of about 20 μm. Bi
13.5 parts of a sazo pigment (P-2), polyvinyl butyral
Le (manufactured by Union Carbide Plastics, product name: X
YHL) 5.4 parts, THF 680 parts and ethylcello
After pulverizing and mixing 1020 parts of Solve in a ball mill,
Add 1700 parts of Circellosolve, stir and mix to generate charge
A layer coating liquid was obtained. Apply this coating solution on the charge transport layer
Spray coated and dried at 100 ° C for 10 minutes
A 0.2 μm charge generation layer was formed. In addition, this charge
A polyamide resin (trade name: CM-
8000) in methanol / n-butanol.
-Coated and dried at 120 ° C for 30 minutes, about 0.5μm thick
Of the photosensitive member No. 25 were created. COMPARATIVE EXAMPLE The diamine compound was 4,4 ',
Except for changing to 4 ''-trimethyltriphenylamine
In the same manner as in Example 5, the comparative example photoconductor (photoconductor No. 2)
6) was prepared. The photosensitive member No. thus prepared is 1
-25 and Comparative Example Photoconductor
Using a test device (SP428, manufactured by Kawaguchi Electric Works)
-6KV or + 6KV corona discharge for 20 seconds
After charging the battery, leave it in a dark place for 20 seconds.
Measure the surface potential Vpo (volts) and then tungsten
Lamp light, the illuminance on the photoreceptor surface becomes 4.5 lux
Until the surface potential becomes 1/2 of Vpo
Obtain the time (second) and calculate the exposure amount E1 / 2 (looks / second).
Calculated. Table 4 shows the results. [0046] [Table 4]The photosensitive member No. 1 to 25 photoconductors
After charging using a commercially available electrophotographic copier,
Irradiate light to form an electrostatic latent image.
After developing using an image agent, the resulting image (toner image) is
Clear transfer image after electrostatic transfer and fixing on paper passing
was gotten. The same applies when a wet developer is used as the developer.
A clear image was obtained. [0048] As described above, according to the present invention, the photosensitive layer
The above specific diamine compound is contained as a photoconductive material.
This gives an electrophotographic photoreceptor with excellent sensitivity
You. That is, as shown in Table 4, Vpo (volt) and
And E1 / 2 (looks / seconds) vary between measured values.
This is due to the difference in charge generation materials and formulation.
And the properties are excellent.
Photoreceptor using compound causes difference in charge generating substance and formulation
Therefore, it is clear that good characteristics can be obtained. Further
However, photoreceptors using this diamine compound are cost effective.
Efficient manufacturing can be performed.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic sectional view showing an example of the electrophotographic photosensitive member of the present invention. FIG. 2 is a schematic sectional view showing another example of the electrophotographic photosensitive member of the present invention. FIG. 3 is a schematic sectional view showing still another example of the electrophotographic photosensitive member of the present invention. FIG. 4 is a schematic sectional view showing still another example of the electrophotographic photosensitive member of the present invention. FIG. 5 is a schematic sectional view showing still another example of the electrophotographic photosensitive member of the present invention. [Description of Signs] 1 conductive support 2, 2 ′, 2 ″, 2 ′ ″, 2 ″ ″ photosensitive layer 3 charge generation layer 4 charge transport medium 5 charge generation layer 6 protective layer

──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Tetsuro Suzuki 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Co., Ltd. (56) References JP 5-249716 (JP, A) JP 5-224439 (JP, A) JP-A-4-356052 (JP, A) JP-A-4-330079 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G03G 5/00 CA (STN) REGISTRY (STN)

Claims (1)

(57) Claims 1. A photosensitive layer containing at least one kind of a diamine compound represented by the following general formula (I) as a photoconductive material is provided on a conductive support. A photoconductor for electrophotography, characterized by Embedded image (Wherein, R ¹ , R ² and R ³ represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an acetyl group, and may be the same or different; Ar ¹ is Represents a substituted or unsubstituted arylene group, Ar ² represents a substituted or unsubstituted aromatic hydrocarbon trivalent group, and R ¹ and R ² or R ¹ and Ar ¹ are taken together with N X may represent a substituted or unsubstituted alkylene group or a substituted or unsubstituted cycloalkylidene group, and n represents an integer of 1 or 2.)