JPH04330042A - Bistyryl compound and electrophotographic photosensitive unit - Google Patents

Abstract

PURPOSE:To obtain a bistyryl compound, usable also for copiers, printers, etc., and suitable as a carrier transport substance for highly sensitive and durable photosentive units. CONSTITUTION:Compounds expressed by formula I [(n) is 0 or >1; R<1> and R<2> are halogen, CN or halogenated alkyl, provided that Cl and CN are not located at the 4-position when (n) is 0; Ar<1> and Ar<2> are formulas II to IV (R<3> to R<5> are H, halogen, CN, OH, alkyl, phenyl, etc.; (x), (y) and (z) are >=0]. A compound expressed by formula V in the aforementioned compounds is obtained by reacting a compound expressed by formula VI and derived from 2-fluoro-6-methylaniline with a compound expressed by formula VII and derived from benzophenone. Image defects and defective images such as white dots, black spots, fogging, deterioration in density, etc., are not caused and sensitivity is high. Thereby, excellent images are obtained at a low residual potential without producing the image defects and defective images even in repeated use by its assembly into high-speed copiers or printers.

Description

Detailed Description of the Invention [0001] [Industrial Application Field] The present invention relates to bisstyryl compounds and
Regarding electrophotographic photoreceptors, especially carrier-generating substances and carriers,
An electrophotographic photosensitive layer having a photosensitive layer containing a rear transport substance
Bistyrene suitable as the carrier transport substance in the body
This invention relates to lyle compounds and electrophotographic photoreceptors. [Prior Art] Conventionally, electrophotographic photoreceptors have been made of selenium,
Inorganic photoconductors such as zinc oxide, cadmium sulfide, silicon, etc.
Photoreceptors containing as a main component were widely known. death
However, these properties do not necessarily satisfy properties such as thermal stability and durability.
It is not something that can be added, and there are also problems in manufacturing and handling.
There was a problem. [0003] On the other hand, photoconductive compounds mainly composed of organic photoconductive compounds
A photoreceptor having a photosensitive layer is relatively easy to manufacture.
, low cost, easy handling, and one
It generally has better thermal stability than selenium photoreceptors. like this
Examples of the organic photoconductor compound include poly-N-vinyl carbon.
Rubazole is well known, and it and 2,4,7-t
formed from Lewis acids such as linitro-9-fluorenone.
A photoreceptor having a photosensitive layer containing a charge transfer complex as a main component
has already been put into practical use. On the other hand, the carrier generation function of the photoconductor
Assign the carrier transport function to separate substances.
Has a laminated type or single layer type functionally separated photosensitive layer.
Photoreceptors that do this are known. For example, amorphous selenium thin layer
A carrier generation layer consisting of poly-N-vinylcarbazo
and a carrier transport layer containing silica as a main component.
Photoreceptors having a light layer have already been put into practical use. However, poly-N-vinylcarbazole
, lacks flexibility, and its coating is hard and brittle, prone to cracking and
The film is easily peeled off, and photoreceptors using this film have poor durability.
is inferior. Therefore, we added plasticizer to improve this drawback.
If it is good, the residual potential will be large in the electrophotographic process.
The residual potential accumulates with repeated use,
The fog gradually increases, damaging the copied image. [0006] In addition, low-molecular organic photoconductive compounds are
Generally, it does not have film-forming ability, so it can be used in combination with an appropriate binder.
In selecting the type of binder, composition ratio, etc.
It is possible to control the physical properties or photosensitive characteristics of the film to some extent.
However, it is preferable in that it has high compatibility with the binder.
The types of organic photoconductive compounds that can be used are limited. In reality
Binder species that can be used in the composition of the photosensitive layer of electrophotographic photoreceptors
There are few types. For example, US Pat. No. 3,189,447
2,5-bis(p-diethylaminophenyl
)-1,3,4-oxadiazole is an electrophotographic photoreceptor.
Binders commonly used as materials for photosensitive layers, such as
Low compatibility with polyester and polycarbonate. vinegar
In other words, at the rate required to adjust the electrophotographic characteristics.
When mixed to form a photosensitive layer, oxidation occurs at a temperature of 50°C or higher.
Diazole crystals begin to precipitate, reducing charge retention and
This method has the disadvantage that electrophotographic properties such as sensitivity and sensitivity deteriorate. In contrast, US Pat. No. 3,820,989
The diarylalkane derivatives described in this issue are binders.
Although there are few compatibility problems with
Repeated transfer in which small particles are repeatedly charged and exposed to light.
When used in electrophotographic photoreceptors, the sensitivity of this photosensitive layer increases.
It has the disadvantage of gradually decreasing. [0009] Also, US Pat. No. 3,274,000,
Special Publication No. 47-36428 has different types of
Phenothiazine derivatives have been described, but none of them are sensitizing.
It has the disadvantages of low luminous intensity and low stability during repeated use.
Ta. [0010] Also, JP-A No. 58-65440, JP-A No. 58-65440,
Described in No. 8-190953 and No. 63-149652.
The charge holding power and sensitivity of the stilbene compounds are comparable.
Although the performance is relatively good, the durability after repeated use is not satisfactory.
It's not something I can afford. [0011] On the other hand, Japanese Patent Application Laid-open No. 175052/1983
, No. 60-174749, No. 62-120346,
No. 64-32265, Japanese Patent Application Publication No. 1-106069,
No. 1-93746, No. 1-274154, etc.
Effects of using distilbene compounds as carrier transport substances
The photoreceptor is a photoreceptor that has almost solved the above drawbacks, but it has complex
Durability when incorporated into photo machines, printers, etc. and used repeatedly
Sex is not satisfying. In particular, the following four points were problematic. 1) In high-speed copying machines with high linear speed, charging, exposure, and removal
Because the power cycle is shortened, residual power is reduced during repeated copying.
The rank will rise significantly. 2) In the case of a copying machine, in the case of repeated copying
In some cases, small white dot-like image defects (called white dots) appear in solid black areas.
) will occur. 3) In the case of a reversal development printer, at a low temperature
Exposure potential (VL) increases and becomes charged due to repeated use.
A defect has been found in which the potential (VH) decreases.
. 4) Image defects in the form of small black dots in white areas (
[0016] In this way, when producing an electrophotographic photoreceptor,
Carrier transport materials with practically satisfactory properties are
The current situation is that it has not been discovered yet. OBJECT OF THE INVENTION The object of the present invention is to provide copiers, printers, etc.
Carrier transport for highly sensitive and durable photoreceptors that can be used for
Provides a compound suitable as a transport substance and an electrophotographic photoreceptor.
There are many things. Furthermore, another object of the present invention is to achieve the following (1)
) to (4). (1) In a high-speed copying machine with a high linear speed,
Residual potential does not increase even after repeated charging, exposure, and neutralization.
Compounds suitable as carrier transport materials for photoreceptors and
To provide an electrophotographic photoreceptor. (2) When used in a copying machine, repeated
Even after repeated use, small white dots are missing in the solid black area.
Carrier import for photoreceptors that does not cause defects (called white spots)
Providing compounds suitable as transport substances and electrophotographic photoreceptors
to do. (3) Built-in use in a reversal development printer
Even when used repeatedly, the exposure potential (V
L ) does not increase, and the charging potential (VH
) is suitable as a carrier-generating material for photoreceptors that does not reduce
An object of the present invention is to provide a suitable compound and an electrophotographic photoreceptor. (4) Image defects in the form of small black dots in white areas
Carrier transport for photoreceptors that does not cause black spots (referred to as black spots)
Provides a compound suitable as a substance and an electrophotographic photoreceptor
thing. Structure of the invention and its effects] That is, the present invention has the following features:
Bisstyryl compound represented by general formula [I] or [II]
electrophotographic photosensitive material containing this compound and this bisstyryl compound
It is related to the body. embedded image [However, n=0 or n>1. When n=0, R1
is placed in the 2- or 3-position relative to the substituted amino group.
chlorine atom or cyano group, or 2- to 4
− Fluorine atom, bromine atom, iodine atom substituted in position
Uron atom or halogenated alkyl group, n>1
When R 1 is 2- to 4 with respect to the substituted amino group
− Halogen atom, cyano group or
is a halogenated alkyl group having 1 to 4 carbon atoms. R
2 may be different from each other, and halogen atoms, silicon
Ano group, alkyl group having 1 to 4 carbon atoms, and number of carbon atoms
A substituent selected from 1 to 4 halogenated alkyl groups.
Ru. Ar1 and Ar2 may be different from each other and are aryl groups represented by the following formula. {However, x≧0, y≧0
, z≧0, and when x, y, and z are 2 or more, multiple
R3, R4, and R5 may be different from each other, and water
Elementary atoms, halogen atoms, cyano groups, hydroxyl groups, phenyl groups
, aralkyl group, alkyl group having 1 to 4 carbon atoms, carbon
A halogenated alkyl group having 1 to 4 atoms, [Formula 17] (However, R6 and R7 may be different from each other.
, an alkyl group or an aralkyl group having 1 to 4 carbon atoms.
Ru. ) and -OR8 (where R8 has 1 to 4 carbon atoms)
is an alkyl group. ) is a substituent selected from }
] [Chemical formula 18] [However, n=0 or n>1. When n=0, R1
1 is placed at the 2- or 3-position relative to the substituted amino group
a methoxy group or diethylamino group, or
Ethoxy group substituted at 2- to 4-positions or
is a dimethylamino group, and when n>1, R11 is substituted
methoxy substituted at the 2- to 4-position relative to the amino group
cy group, ethoxy group, dimethylamino group or diethylamino group
It is a radical. R12 may be different from each other, and R12 is a halogen atom,
Cyano group, alkyl group having 1 to 4 carbon atoms, methoxy group
, ethoxy group, dimethylamino group and diethylamino group
A substituent selected from Ar3 and Ar4 are each other
may be different from each other, and is an aryl group represented by the following formula. {However, x≧0, y≧0
, z≧0, and when x, y, and z are 2 or more, multiple
R13, R14, and R15 may be different from each other,
Hydrogen atom, halogen atom, cyano group, hydroxyl group, phenyl
group, aralkyl group, alkyl group having 1 to 4 carbon atoms, [
Chemical formula 20] (However, R16 and R17 may be different from each other.
, an alkyl group or an aralkyl group having 1 to 4 carbon atoms.
Ru. ), -OR18 (however, R18 has 1 to 4 carbon atoms
is an alkyl group. ), -R19COOR20 (however
, R19 is an alkylene group having 1 to 4 carbon atoms, and R
20 is an alkyl group. ) and -R19OCOR20
A substituent selected from }However, the following compounds are excluded.
Ku. [Chemical Formula 21] (Here, the plurality of R21 and R22 are different from each other.
It is an alkyl group having 1 to 4 carbon atoms. Further, r≧2 and t≧0. )] [0025] The above general formulas [I] and [II] of the present invention
The compound has the following characteristics A to C, and is suitable for electrophotography.
It is suitable as a carrier transport material for photoreceptors. (A). Has a substituent in the molecule and has a pair of strips.
Since the tyryl group is a bis-styryl compound with an asymmetric structure,
As a result, sensitivity and durability are improved, and fluctuations in charging potential are reduced.
Because it is small, it can be incorporated into copiers, printers, etc. and repeated.
When used repeatedly, white spots, black spots, fogging, and low density may occur.
A good image is obtained without any image defects or image defects.
It will be done. (B). Moreover, high-speed copiers and printers
-When used repeatedly, the residual potential is small.
It is possible to obtain a good image without image defects or image defects.
An image is obtained. (C). Since it is a bisstyryl compound, it is easy to synthesize.
be. Specific compound No. of the above general formula [I].
<1> to <189> are collectively illustrated below. Next, an example of synthesis of the compound of general formula [I] will be explained.
However, the outline of the synthesis recipe is shown below. (Synthesis Example 1: Synthesis of Exemplary Compound <23>)
Diformyl compound 3 was synthesized as follows according to known methods.
went. 2-Fluoro-6-methylaniline 1 (Tokyo
Seisha) (1 molar ratio) and iodobenzene (Tokyo Kasei)
) (2.5 molar ratio) and potassium carbonate (manufactured by Kanto Kagaku Co., Ltd.)
(2 molar ratio) and copper powder (manufactured by Kanto Kagaku Co., Ltd.) (0.2 molar ratio)
) and reacted for 50 hours at an internal temperature of 190 to 210 °C.
, column purification after post-treatment to obtain 2-fluoro-6-methylene
lutriphenylamine 2 was obtained in a yield of 60% (Ullmann
reaction). 2-Fluoro-6-methyltriphenyla
N,N-dimethylformamide (
manufactured by Kanto Kagaku Co., Ltd.) (4 molar ratio) and phosphorus oxychloride (Wako Pure
(manufactured by Yaku Kogyo Co., Ltd.) (3 molar ratio) and heated at an internal temperature of 70 to 90°C.
React for 24 hours, and after post-treatment, column purification is performed to obtain N,N-bi
(4-formyl-phenyl)-2-fluoro-6-meth
Thiraniline 3 was obtained in a yield of 55% (Vilsmeyer reaction).
Response). [0032] The synthesis of diethyl phosphonate is a known method.
The procedure was carried out as follows. Methanol (manufactured by Kanto Kagaku Co., Ltd.)
) in which benzophenone (manufactured by Tokyo Kasei Co., Ltd.) (1 molar ratio)
Sodium borohydride (manufactured by Kanto Kagaku Co., Ltd.) (0.5
molar ratio) and reacted at an internal temperature of 10 to 20°C for 5 hours,
After post-treatment, column purification was performed to obtain the hydroxy compound in a yield of 92%.
(reduction reaction). Hydrochloride in toluene (manufactured by Wako Pure Chemical Industries, Ltd.)
Add the xyl compound (1 molar ratio) and add thionyl chloride (Tokyo
(manufactured by Kasei Co., Ltd.) (1.2 molar ratio), and the internal temperature was 10-2.
The reaction was carried out at 0°C for 2 hours, and after post-treatment, the chloride was obtained in a yield of 93.
% (substitution reaction). [0034] Triethyl phosphite is added to the chloride (1 molar ratio).
(manufactured by Kanto Kagaku Co., Ltd.) (1.2 molar ratio), and
React at 140 to 160 °C for 10 hours, then evaporate after post-treatment.
Distillation purification was performed to obtain diethyl phosphonate in a yield of 90%.
(Phosphonic acid diethylation reaction). Synthesis of CTM is carried out using the compound obtained as described above.
Using the compound as a raw material, the following procedure was performed. N,N-bis
(4-formyl-phenyl)-2-fluoro-6-methy
12.2 g (0.033 mol) of luaniline and 1,1-
Diethyl diphenylmethylphosphonate 20g (0.06
6 mol) and 50 m of toluene (manufactured by Wako Pure Chemical Industries, Ltd.)
Dissolved in l. Sodium methoxide (manufactured by Kanto Kagaku Co., Ltd.)
) 3.6 g (0.066 mol) in 50 ml of toluene
Place this in a refrigerator and cool on ice, keeping the internal temperature below 25℃.
The solution was added to the above solution. Then, it was stirred at room temperature for 3 hours.
. Add 100ml of water, wash the toluene layer with water, and then
, water from the toluene layer with sodium sulfate (manufactured by Kanto Kagaku Co., Ltd.)
The solvent was distilled off, and the resulting residue was passed through a silica column.
Purify the desired exemplary compound <23> as yellow-white crystals.
14.3 g (0.023 mol) was obtained with a yield of 70%. The melting point was 123-125°C. Former
The elementary analysis values were as follows. IR data of exemplified compound <23> (spectrum shown in Figure 1)
). 1595cm-, S (Strong:
The same applies hereafter) (Synthesis Example 2. Exemplary Compound <32
) In Synthesis Example 1, 2-fluoro-6-methylani
Synthesis except that phosphorus was replaced with 3,4-dichloroaniline
Synthesized in the same manner as in Example 1, giving the exemplified compound as yellow-white crystals.
15.4 g (0.023 mol) was obtained with a yield of 70%. The melting point was 118-124°C. Former
The elementary analysis was as follows. (Synthesis Example 3. Synthesis of Exemplary Compound <67>)
In Synthesis Example 1, benzophenone was converted into 4-methylbenzophenone.
Synthesis was performed in the same manner as in Synthesis Example 1, except that the
The compound was obtained as yellow-white crystals in a yield of 55%, 12 g (0.0
18 mol) was obtained. The melting point was 106-111°C. Former
The elementary analysis was as follows. (Synthesis Example 4. Synthesis of Exemplified Compound <61>)
In Synthesis Example 1, 2-fluoro-6-methylaniline was converted into 2-
Replaced chloro-4-methylaniline with benzophenone
Same as Synthesis Example 1 except that 4-methylbenzophenone was used.
Synthesized in the same manner, yielding the exemplified compound as yellow-white crystals.
11.6 g (0.017 mol) was obtained at 52%. The melting point was 117-122°C. Former
The elementary analysis was as follows. (Synthesis Example 5. Exemplary Compound <4
7> Synthesis) In Synthesis Example 1, 2-fluoro-6-methyla
Replace niline with 4-bromoaniline and replace benzophenone with
Same as Synthesis Example 1 except that 4-methylbenzophenone was used.
Synthesized in the same manner, yielding the exemplified compound as yellow-white crystals.
12 g (0.018 mol) were obtained at 55%. The melting point was 119-125°C. Former
The elementary analysis was as follows. Next, specific compounds of the above general formula [II]
No. (1) to (319) are summarized as examples below.
Indicated. Next, a synthesis example of the compound of general formula [II] will be described.
To explain, a schematic diagram of the synthesis recipe is shown below. (Synthesis Example 6: Synthesis of Exemplified Compound (24))
The formyl compound was synthesized as follows according to a known method.
Ta. 5-chloro-2-methoxyaniline (manufactured by Aldrich)
(1 molar ratio) and iodobenzene (manufactured by Tokyo Kasei Co., Ltd.) (2.
5 molar ratio) to potassium carbonate (manufactured by Kanto Kagaku Co., Ltd.) (2 mol
(ratio) and copper powder (manufactured by Kanto Kagaku Co., Ltd.) (0.2 molar ratio) were added.
, reacted for 50 hours at an internal temperature of 190 to 210 °C, and then post-treated
After column purification, 5-chloro-2-methoxytrif
Phenylamine was obtained in a yield of 55% (Ullmann reaction). 5-chloro-2-methoxytriphenyla
Niline (1 molar ratio) and N,N-dimethylformamide (
manufactured by Kanto Kagaku Co., Ltd.) (4 molar ratio) and phosphorus oxychloride (Wako Pure
(manufactured by Yaku Kogyo Co., Ltd.) (3 molar ratio) and heated at an internal temperature of 70 to 90°C.
React for 24 hours, and after post-treatment, column purification is performed to obtain N,N-bi
(4-formyl-phenyl)-5-chloro-2-meth
Xyaniline was obtained in a yield of 45% (Vilsmeier reaction).
). The diethyl phosphonate compound is synthesized by a known method.
The procedure was carried out as follows. Methanol (manufactured by Kanto Kagaku Co., Ltd.)
) in which benzophenone (manufactured by Tokyo Kasei Co., Ltd.) (1 molar ratio)
Sodium borohydride (manufactured by Kanto Kagaku Co., Ltd.) (0.5
molar ratio) and reacted at an internal temperature of 10 to 20°C for 5 hours,
After post-treatment, column purification is performed to obtain hydroxyl derivatives with a yield of 90%.
(reduction reaction). Hydrochloride in toluene (manufactured by Wako Pure Chemical Industries, Ltd.)
Add the xyl compound (1 molar ratio) and add thionyl chloride (Tokyo
(manufactured by Kasei Co., Ltd.) (1.2 molar ratio), and the internal temperature was 10-2.
The reaction was carried out at 0°C for 2 hours, and after post-treatment, the chloride was obtained in a yield of 94.
% (substitution reaction). Triethyl phosphorous acid added to the chloride (1 molar ratio)
(manufactured by Kanto Kagaku Co., Ltd.) (1.2 molar ratio), and
React at 140 to 160 °C for 10 hours, then evaporate after post-treatment.
Distillation purification was performed to obtain diethyl phosphonate in a yield of 91%.
(Phosphonic acid diethylation reaction). Synthesis of CTM is carried out using the compound obtained as described above.
Using the compound as a raw material, the following procedure was performed. N,N-bis
(4-formyl-phenyl)-5chloro-2-methoxy
12 g (0.033 mol) of aniline and 1,1-dife
20 g (0.066 mole diethyl methylphosphonate)
) in 50 ml of toluene (manufactured by Wako Pure Chemical Industries, Ltd.).
I understand. Sodium methoxide (manufactured by Kanto Kagaku Co., Ltd.) 3.
Put 6 g (0.066 mol) in 50 ml of toluene.
, while keeping the internal temperature below 25℃ under ice cooling.
Added to the above solution. Thereafter, the mixture was stirred at room temperature for 3 hours. water 1
00ml was added, the toluene layer was washed with water, and then sulfuric acid was added.
Remove water from the toluene layer with sodium (manufactured by Kanto Kagaku Co., Ltd.)
, the solvent was distilled off, and the resulting residue was purified on a silica column.
, the target exemplary compound (24) was collected as yellow-white crystals.
14.3 g (0.021 mol) was obtained at a yield of 65%. The melting point was 110-115°C. Former
The elementary analysis values were as follows. IR data of exemplary compound (24) (spectrum shown in Figure 2)
). 1950cm-1,S 0054] (Synthesis Example 7. Synthesis of Exemplary Compound (21))
In Synthesis Example 6, 5-chloro-2-methoxyaniline was converted into 3-
Same procedure as Synthesis Example 6 except that methoxyaniline was used.
The exemplified compound was synthesized as yellow-white crystals in a yield of 60%.
12.5 g (0.0197 mol) was obtained. The melting point was 110-115°C. Former
The elementary analysis was as follows. (Synthesis Example 8. Synthesis of Exemplified Compound (206)
Synthesis) In Synthesis Example 6, 5-chloro-2-methoxyaniline was
1,1-diphenyl instead of 2,4-methoxyaniline
Diethyl methylphosphonate to 1-phenyl-1-P-t
Synthesis example except for changing to diethyl lylmethylphosphonate
Synthesize the exemplified compound in the same manner as in 6 as yellow-white crystals.
14.1 g (0.02 mol) was obtained with a yield of 62%. The melting point was 107-111°C. Former
The elementary analysis was as follows. The above general formula [I] and
Containing a compound of general formula [II] as a carrier transport substance
The electrophotographic photoreceptor may take the form shown in FIGS. 3 to 8.
I can do it. That is, in FIGS. 3 and 4, the conductive support 1
A carrier generation layer 2 containing a carrier generation substance as a main component on top
and a carrier transport substance based on the present invention as a main component.
A photosensitive layer 4 consisting of a laminate with a carrier transport layer 3 is provided.
Let's go. As shown in FIGS. 5 and 6, the photosensitive layer 4 is electrically conductive.
It may be provided via an intermediate layer 5 provided on the support 1. When the photosensitive layer 4 has a two-layer structure as described above,
A photoreceptor having excellent electrophotographic properties can be obtained. In addition, in the present invention, as shown in FIGS. 7 and 8,
In order to
A conductive support layer 4 comprising a photosensitive layer 4 dispersed in a layer 6 containing
It may be provided directly on the support 1 or via the intermediate layer 5.
. In addition, in the present invention, as shown in the virtual line in FIG.
In particular, a protective layer 7 may be provided as the outermost layer. [0063] General formula [I] and general formula [
Compound II] has poor coating-forming ability by itself.
Then, a photosensitive layer is formed by combining various binders. [0064] Any binder can be used here.
However, it is hydrophobic and has a high dielectric constant.
It is preferable to use an electrically insulating film-forming polymer.
Delicious. [0065] Examples of such high molecular weight polymers include, for example,
May include, but are not limited to:
It's not a thing. (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-1
0) Vinylidene chloride-acrylonitrile copolymer (P-11) Vinyl chloride-vinyl acetate copolymer (P-11)
-12) Vinyl chloride-vinyl acetate-maleic anhydride
Copolymer (P-13) Silicone resin (P-14) Silicone-alkyd resin (P-1
5) Phenol formaldehyde resin (P-16)
Styrene-alkyd resin (P-17) Poly-
N-vinylcarbazole (P-18) polyvinyl carbazole
Chyral (P-19) Polyvinyl formal [0
[067] These binder resins may be used alone or in combination of two or more.
Can be used as a mixture of the above. CTMs that can be used in combination in the present invention
There are no particular restrictions on the method, but for example, oxazole induction
body, oxadiazole derivatives, thiazole derivatives, thia
Diazole derivatives, triazole derivatives, imidazole
derivatives, imidazolone derivatives, imidazolidine derivatives,
Bisimidazolidine derivatives, styryl compounds, hydrazo
compounds, pyrazoline derivatives, amine derivatives, oxazo
Ron derivatives, benzothiazole derivatives, benzimidazo
derivatives, quinazoline derivatives, benzofuran derivatives,
Acridine derivatives, phenazine derivatives, aminostilbe
derivatives, poly-N-vinylcarbazole, poly-1-
vinylpyrene, poly-9-vinylanthracene, etc.
. [0069] The CTM used in the present invention is
Excellent ability to transport holes generated during light irradiation to the support side
In addition, combinations with the organic pigments described below used in the present invention
Those suitable for matching are preferred. [0070] For use in the carrier generation layer of the photosensitive layer according to the present invention.
Possible carrier-generating substances include the following:
Can be mentioned. (1) Monoazo dye, bisazo dye, tri-
Azo dyes such as suazo dyes (2) Perylenic acid anhydride, perylenic acid imide, etc.
Ren-based pigments (3) Indigo-based pigments such as indigo and thioindigo (
4) Anthraquinone, pyrenequinone and flavanthro
(5) Quinacridone dyes (6) Bisbenzimidazole dyes (7) Indathrone dyes (8) Squarylium dyes (9) Cyanine dyes (10) Azulenium dyes ( 11) Triphenylmethane dye (12) Amorphous silicon (13) Metal phthalocyanine, metal-free phthalocyanine
Which phthalocyanine pigments (14) selenium, selenium-tellurium, selenium-arsenic (15
) Cds, CdSe, (16) Pyrylium salt dye, thiapyrylium salt dye, etc.
can be used alone or as a mixture of two or more
You can also In the electrophotographic photoreceptor according to the present invention,
As CGM, fluorenone bisazo pigment, fluorene
Organic pigments such as redene-based bisazo pigments and polycyclic quinone pigments
is preferably used. In particular, the general formula shown below [
F1 ] fluorenone bisazo pigment, fluorenyl
Dense bisazo pigments and polycyclic quinone pigments are used in the present invention
and significantly improved effects in terms of sensitivity, durability, image quality, etc.
Show results. [0073] Fluorenone-based compounds that can be used in the present invention are described below.
Specific examples of bisazo pigments (F1-1 to F1-24)
However, the invention is not limited thereto. General formula [F1] below that can be used in the present invention
The fluorenone bisazo pigment represented by
For example, Japanese Patent Application No. 62-30486
It is synthesized by a method such as No. 2. Fluorenylidene-based vinyl that can be used in the present invention
The suazo pigment is represented by the general formula [F2] below. Effective for the present invention represented by the general formula [F2]
As a specific example of a bisazo pigment, for example, the structural formula shown below is
List the following (F2-1 to F2-7):
However, this makes it possible to
The pigments are not limited. The polycyclic quinone pigment that can be used in the present invention is
It is represented by the following general formulas [Q1] to [Q3]. [Q1] to [Q3] shown below
Specific examples of polycyclic quinone pigments that can be used in the present invention are given below.
However, it is not limited to this. Antanthro represented by the general formula [Q1]
Specific compound examples of pigments (Q1-1 to Q1-6)
They are listed below. Dibenzpyre represented by the general formula [Q2]
Specific compound examples of quinone pigments (Q2-1 to Q2-
5) is listed below. Pyrantrone represented by the general formula [Q3]
Specific examples of pigment compounds (Q3-1 to Q3-4) are listed below.
It is as described below. General formulas [Q1] to [Q1] that can be used in the present invention
Q3 ] The polycyclic quinone pigment represented by
can be easily synthesized. Metal-free phthalocyanine that can be used in the present invention
As a pigment, metal-free phthalocyanine with photoconductivity is used.
All derivatives thereof can be used, but for example α
type, β type, τ, τ′ type, η, η′ type, Χ type, and JP-A-Sho
Crystal forms described in No. 62-103651 and derivatives thereof, etc.
can be used. Especially when using τ, Χ, K/R-Χ types,
It is desirable that For Χ-type metal-free phthalocyanine, the United States
Described in Patent No. 3,357,989, τ-type metal-free
Regarding phthalocyanine, see JP-A-58-182639.
There is a description in . [0085] K/R-X type is disclosed in Japanese Patent Application Laid-Open No. 103651/1986.
As stated in the issue, CuKα is resistant to 1.541 Å X-rays.
At the Bragg angle (2θ±0.2 degrees), 7.
7, 9.2, 16.8, 17.5, 22.4,
It has a major peak at 28.8 degrees and a peak of 9.2 degrees.
The peak intensity ratio of 16.8 degrees to the peak intensity is 0.8
~1.0 and 28.8 for 22.4 degrees
A film characterized by a peak intensity ratio of 0.4 or more.
It is talocyanin. Oxytitanyl phthalo usable in the present invention
Cyanine is represented by the general formula [TP] below. [0087] Those that can be used in the present invention are shown below.
Different crystal forms are known that have been disclosed in patents.
. For example, JP-A-61-239248, JP-A No. 62-670
No. 943, No. 62-272272, No. 63-1161
No. 58 or No. 64-17066, JP-A-2-282
No. 65, No. 2-215866, and the like. Dispersion medium for organic pigments that can be used in the present invention
There are known dispersion media such as methyl ethyl ketone. [0089] In the present invention, the photosensitive layer may contain one or two types.
The above known electron-accepting substances can be contained.
Ru. The addition ratio of the electron-accepting substance used in the present invention is determined by weight ratio.
Organic pigment that can be used: Electron accepting substance = 100:
0.01-200, preferably 100:0.1
~100. In addition, the addition ratio of electron-accepting substances is
Weight ratio of total CTM:electron-accepting substance=100:0
．． 01-100, preferably 100:0.1-
It is 50. [0090] Also, CGM (carrier generating material) is contained in the photosensitive layer.
Organic amines are added to improve the charge generation function of
It is particularly preferred to add secondary amines.
Yes. These compounds are disclosed in JP-A No. 59-218447,
It is described in No. 62-8160. [0091] In addition, in the photosensitive layer, ozone deterioration prevention
For example, the antioxidant of JP-A-63-18354
can be added. The amount of antioxidant added is CTM
0.1 to 100 parts by weight per 100 parts by weight, preferably
Preferably 1 to 50 parts by weight, particularly preferably 5 to 25 parts by weight
Department. [0092] The photoreceptor according to the present invention also includes other necessary components.
Contains ultraviolet absorber, etc. to protect the photosensitive layer as necessary.
It may also contain a dye for color sensitivity correction. [0093] An intermediate layer may be provided between the photosensitive layer and the support.
However, this intermediate layer can be used as an adhesive layer, blocking layer, etc.
It's something that works. In the present invention, the photosensitive layer is composed of two layers as shown in FIG.
When configured, the CGL (carrier generation layer) is electrically conductive.
directly on the support or CTL (carrier transport layer)
If necessary, add an adhesive layer or blocking layer, etc.
After providing an intermediate layer, it can be formed by the following method.
can. (1) Vacuum deposition method (2) CGM was dissolved in a suitable solvent
Method of applying the solution (3) Ball mill or sandog CGM
Required as fine particles in dispersion medium by liner etc.
Depending on the situation, apply a dispersion obtained by mixing and dispersing with a binder.
how to. Specifically, vacuum evaporation, sputtering
Vapor phase deposition methods such as gluing, CVD, dipping, and spraying
Application methods such as ray, blade, and roll methods may be used arbitrarily.
It will be done. The thickness of the CGL formed in this way is
, preferably 0.01 μm to 5 μm, more preferably
Preferably, it is 0.05 μm to 3 μm. [0100] Also, regarding CTL, similar to CGL,
It can be formed by The thickness of CTL depends on the required
Although it can be changed depending on the size, it is usually 5 μm to 60 μm.
is preferred. [0101] The composition ratio in this CTL is based on the composition ratio of the present invention.
0.1 to 5 parts by weight of binder per 1 part by weight of CTM
It is preferable to disperse CGM in the form of fine particles.
When forming the photosensitive layer 4, add a buffer to 1 part by weight of CGM.
It is preferable to use indica in an amount of 5 parts by weight or less. In addition, when CGL is configured as a dispersed type in a binder,
If the binder is 5 parts by weight or more per 1 part by weight of CGM,
It is preferable to use the following range. The electrophotographic photoreceptor according to the present invention is as described above.
As is clear from the examples described later,
, has excellent charging characteristics, sensitivity characteristics, image forming characteristics, etc.
Particularly durable, with little fatigue deterioration even after repeated use.
It has excellent properties. Furthermore, the electrophotographic photoreceptor according to the present invention
In addition to photocopy machines, lasers, cathode ray tubes (CRTs), and
Photoreceptor of a printer that uses a photodiode (LED) as a light source
It can also be widely used in other application fields. Also, books
In addition to such photoreceptors, the invention also includes EL (electroluminescence).
It can also be applied to other applications such as (minescence), etc. [Examples] Hereinafter, specific examples of the present invention will be explained.
However, this does not limit the embodiments of the present invention.
It's not something you can do. Example 1 ε-amino-caproic acid, adipic acid and N-(β-amino-caproic acid)
Monomers with a ratio of 1:1:1 (minoethyl)piperazine
30g of polyamide copolymerized with the composition is heated to 50℃
800 ml methanol EL standard (manufactured by Kanto Kagaku Co., Ltd.)
) was added to 200 ml. After that, an 80mm diameter aluminum
Dip coated onto a mini-drum, 0.6 μm thick
formed a layer. Next, as a CGM, fluorenone-based disa
20g of pigment (exemplary compound F1-23) and binder
Polyvinyl butyral resin S-LEC BX-1
(Manufactured by Sekisui Chemical Co., Ltd.) 10g methyl ethyl ketone (Kanto Kagaku)
Dissolve in 1000 ml (manufactured by Gakusha, EL standard), and
Milling was performed for 24 hours in a mill to obtain a CGL coating solution. This was coated by dip coating on the above intermediate layer to give a thickness of 0.2 μm.
GL was formed. [0107] Then, as a CTM, exemplified compound <10>
140 g and polycarbonate resin “Iupilon Z-
200” (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 165 g
, 2-dichloroethane special grade (manufactured by Kanto Kagaku Co., Ltd.) 1000m
1 to obtain a CTL coating liquid. [0108] After applying this by dip coating on the above CGL, 100%
It was dried at ℃ for 1 hour to form a 23 μm thick CTL. In this way, the intermediate layer-CGL-CTL are sequentially laminated.
A photoreceptor 1 was prepared. Examples 2 to 10 In Example 1, CGM and CTM were exemplified as shown in Table 1 below.
Photoreceptors 2 to 10 were prepared in the same manner as in Example 1 except that they were made into composites.
It was created. Comparative Examples 1 and 2 As shown in Table 1 below, the CTM of Example 1 was compared as shown below.
The same procedure as in Example 1 was carried out except that compounds <1> to <2> were used.
A comparative photoreceptor was created. Example 11 The intermediate layer was formed in the same manner as in Example 1. [0112] As CGM, polycyclic quinone pigments (examples)
compound; Q1-3) 20g and poly as a binder.
Carbonate resin C-1300 (manufactured by Teijin Chemicals) 10g
Dissolved in 1,2-dichloroethane special grade (manufactured by Kanto Kagaku Co., Ltd.)
Milled with a ball mill for 30 hours and coated with CGL.
I got the liquid. This was applied by dip coating on the above intermediate layer to give a 0.6
A CGL with a thickness of μm was formed. Next, CTM exemplified compound <10>,
CTL was laminated in the same manner as in Example 1 to produce photoreceptor <11>.
accomplished. Examples 12 to 20 In Example 11, CGM and CTM were as shown in Table 2 below.
Photoreceptor 12 was prepared in the same manner as in Example 1 except that the compound shown was used.
~20 were created. Comparative Examples 3 to 4 As shown in Table 2 below, CTM in Example 11 was used as a comparative compound.
Comparisons were made in the same manner as in Example 11 except for <3> to <4>.
Comparison photoreceptors 3 and 4 were prepared. Example 21 Polyvinyl butyral resin (S-LEC BX-1, Sekisui Co., Ltd.
(manufactured by Kagakusha) 12g to 1000ml of methyl ethyl ketone
After dissolving, Exemplified Compound Q1-3;5 as CGM
．． 7 g and 0.5 g of exemplified compound F1-23 were mixed.
, and dispersed with a sand grinder for 12 hours. [0117] This was dip coated onto the intermediate layer described in Example 1.
fabric, form CGL, and further exemplify CTM as shown in Table 3.
Compound <10> and form CTL in the same manner as in Example 1.
Then, a photoreceptor 21 was produced. Examples 22 to 30 In Example 21, CGM and CTM were as shown in Table 3 below.
Photoreceptor 2 was prepared in the same manner as in Example 21 except that the compound shown was used.
2 to 30 were created. Comparative Examples 5 and 6 As shown in Table 3 below, CTM in Example 21 was used as a comparative compound.
Comparisons were made in the same manner as in Example 21 except that <5> to <6> were used.
Comparison photoreceptors 5 and 6 were prepared. Example 31 50g of the polyamide used in Example 1 was heated to 50°C.
To 800 ml methanol EL standard (manufactured by Kanto Kagaku Co., Ltd.)
and dissolved. After cooling to room temperature, 1-butanol
200 ml of special grade (manufactured by Kanto Kagaku Co., Ltd.) was added. after that,
Dip coating onto an aluminum drum with a diameter of 80 mm, and
．． An intermediate layer of 5 μm was formed. Next, as a CGM, τ-type metal-free phthalocyanate
40g of Nin (τ-Pc) was mixed with silicone resin “KR-52”.
40'' (solid content 20%) (manufactured by Shin-Etsu Chemical Co., Ltd.) 200 g
Dissolved methyl ethyl ketone EL standard (manufactured by Kanto Kagaku Co., Ltd.)
In addition to 2000ml, use a sand grinder for 4 hours.
The mixture was dispersed to obtain a CGL coating liquid. Place this on the above middle layer
A CGL with a thickness of 0.4 μm was formed by dip coating. [0122] Then, 135 g of exemplified compound <8>
Polycarbonate “Iupilon Z-200” (Mitsubishi Gas
Kagaku Co., Ltd.) 165 g of 1,2-dichloroethane
Dissolve in 1000ml of grade (manufactured by Kanto Kagaku Co., Ltd.) and coat with CTL.
A working solution was obtained. After applying this by dip coating on the above CGL,
Drying was performed at ℃ for 1 hour to obtain a 22 μm thick CTL. A photoreceptor consisting of an intermediate layer, CGL, and CTL laminated in this order.
Created. Examples 32 to 40 In Example 31, CTM was replaced with the exemplified compounds shown in Table 4 below.
Photoreceptors 32 to 40 were prepared in the same manner as in Example 31 except that
It was created. Comparative Examples 7-8 As shown in Table 4 below, CTM in Example 31 was used as a comparative compound.
Comparisons were made in the same manner as in Example 31 except for <1> to <2>.
A comparison photoreceptor was created. Example 41 Using X-type metal-free phthalocyanine (X-Pc) in CGM
The intermediate layer-CGL-C was prepared in the same manner as in Example 31 except that
A photoreceptor was prepared by sequentially laminating TLs. Examples 42 to 50 In Example 41, CTM was converted to exemplified compounds as shown in Table 5 below.
Photoreceptors 42 to 50 were prepared in the same manner as in Example 41 except that
It was created. Comparative Examples 9-10 As shown in Table 5 below, CTM in Example 41 was used as a comparative compound.
Comparisons were made in the same manner as in Example 41 except for <3> to <4>.
A comparison photoreceptor was created. Example 51 Y-type oxytitanium phthalocyanine (Y-T
iOPC) [Journal of Electrophotography Society 250 (2), 29 (
2), 1990] in the same manner as in Example 1.
A photoreceptor made by sequentially laminating an intermediate layer, CGL, and CTL.
It was created. Examples 52 to 60 In Example 51, CTM was replaced with the exemplified compounds shown in Table 6 below.
Photoreceptors 52 to 60 were prepared in the same manner as in Example 51 except that
It was created. Comparative Examples 11-12 As shown in Table 6 below, CTM in Example 51 was used as a comparative compound.
Comparisons were made in the same manner as in Example 51 except that <5> to <6> were used.
A comparison photoreceptor was created. Example 61 Except for using fluorenylidene-based azo CGM as CGM
, the middle layer-CGL-CTL in the same manner as in the above example.
A photoreceptor was created by laminating the following layers. Examples 62 to 70 In Example 61, CGM and CTM were exemplified as shown in Table 7 below.
Photoreceptor 62 was prepared in the same manner as in Example 61 except that a compound was used.
~70 were created. Comparative Examples 13-14 As shown in Table 7 below, CTM in Example 61 was used as a comparative compound.
Comparisons were made in the same manner as in Example 61 except for <1> to <2>.
A comparison photoreceptor was created. Example 71 ε-amino-caproic acid, adipic acid and N-(β-amino-caproic acid)
Monomers with a ratio of 1:1:1 (minoethyl)piperazine
30g of polyamide copolymerized with the composition is heated to 50℃
800 ml methanol EL standard (manufactured by Kanto Kagaku Co., Ltd.)
) was added to 200 ml. After that, an 80mm diameter aluminum
Dip coated onto a mini-drum, 0.6 μm thick
formed a layer. [0135] Next, as a CGM, fluorenone-based disa
20g of pigment (exemplary compound F1-23) and binder
Polyvinyl butyral resin S-LEC BX-1
(Manufactured by Sekisui Chemical Co., Ltd.) 10g methyl ethyl ketone (Kanto Kagaku)
Dissolve in 1000 ml (manufactured by Gakusha, EL standard), and
Milling was performed for 24 hours in a mill to obtain a CGL coating solution. This was coated by dip coating on the above intermediate layer to give a thickness of 0.2 μm.
GL was formed. [0136] Then, 140 g of Exemplified Compound (6) was added to the pot.
Recarbonate resin “Iupilon Z-200” (Mitsubishi
165 g (manufactured by Gas Kagaku Co., Ltd.) of 1,2-dichloroethane
Dissolve in 1000 ml of Tan special grade (manufactured by Kanto Kagaku Co., Ltd.) and
A TL coating liquid was obtained. After applying this on the above CGL by dipping, it was heated at 100 °C for 1 hour.
It was dried to form a 23 μm thick CTL. Do it like this
A photoreceptor made by sequentially laminating an intermediate layer, CGL, and CTL.
71 was created. Examples 72 to 80 In Example 71, CGM and CTM were exemplified as shown in Table 8 below.
Photoreceptor 72 was prepared in the same manner as in Example 71 except that it was made into a compound.
~80 were created. Comparative Examples 15-16 As shown in Table 8 below, the CTM of Example 71 was compared with
Same as Example 71 except that compounds (1) to (2) were used.
A comparative photoreceptor was prepared. Example 81 The intermediate layer was formed in the same manner as in Example 71. As CGM
, polycyclic quinone pigment (exemplary compound; Q1-3) 20
g and polycarbonate resin C-1 as a binder
300 (manufactured by Teijin Chemicals) 10g to 1,2-dichloroetha
Dissolved in special grade (manufactured by Kanto Kagaku Co., Ltd.) and milled in a ball mill for 30 minutes.
Time milling was performed to obtain a CGL coating solution. This is in the above
A 0.6 μm thick CGL was formed by dip coating on the interlayer.
Ta. Next, CTM was used as exemplified compound (2).
Except for this, the CTL was laminated in the same manner as in Example 71, and the photoreceptor 81
It was created. Examples 82 to 90 In Example 81, CGM and CTM were as shown in Table 9 below.
Photoreceptor 8 was prepared in the same manner as in Example 71 except that the compound shown was used.
2 to 90 were created. Comparative Examples 17-18 As shown in Table 9 below, CTM in Example 81 was used as a comparative compound.
Comparisons were made in the same manner as in Example 71 except for (3) and (4).
Comparison photoreceptors 17 and 18 were prepared. Example 91 Polyvinyl butyral resin (S-LEC BX-1, Sekisui Co., Ltd.
(manufactured by Kagakusha) 12g to 1000ml of methyl ethyl ketone
After dissolving, Exemplified Compound Q1-3;5 as CGM
．． 7 g and 0.5 g of exemplified compound F1-23 were mixed.
, and dispersed with a sand grinder for 12 hours. [0144] This was dipped onto the intermediate layer described in Example 71.
Coating to form CGL, and then CGL in the same manner as in Example 71.
A photoreceptor 91 was produced by forming a TL. Examples 92 to 100 In Example 81, CGM and CTM were as shown in Table 10 below.
A photoreceptor was prepared in the same manner as in Example 71 except that the exemplified compounds were used.
92-100 were created. Comparative Examples 19-20 As shown in Table 10 below, CTM in Example 91 was used as a comparative compound.
The same procedure as in Example 91 was carried out, except that items (5) and (6) were used.
Comparative photoreceptors 19 to 20 were prepared. Example 101 50 g of the polyamide used in Example 71 was heated to 50°C.
800 ml methanol EL standard (manufactured by Kanto Kagaku Co., Ltd.)
and dissolved. After cooling to room temperature, 1-butano
200 ml of Le special grade (manufactured by Kanto Kagaku Co., Ltd.) was added. after that
, applied by dip coating onto an aluminum drum with a diameter of 80 mm,
An intermediate layer of 0.5 μm was formed. [0148] Next, as CGM, τ-type metal-free phthalocia
40g of Nin (τ-Pc) was mixed with silicone resin “KR-52”.
40'' (solid content 20%) (manufactured by Shin-Etsu Chemical Co., Ltd.) 200 g
Dissolved methyl ethyl ketone EL standard (manufactured by Kanto Kagaku Co., Ltd.)
In addition to 2000ml, use a sand grinder for 4 hours.
The mixture was dispersed to obtain a CGL coating liquid. Place this on the above middle layer
A CGL with a thickness of 0.4 μm was formed by dip coating. [0149] Thereafter, 135 g of exemplified compound (20)
and polycarbonate “Iupilon Z-200” (Mitsubishi)
Gas Kagaku Co., Ltd.) 165 g of 1,2-dichloroethane
CT
L coating liquid was obtained. After applying this on the above CGL by dip coating, 1
Dry at 00 °C for 1 hour to obtain a 22 μm thick CTL.
Ta. A photosensitive material consisting of an intermediate layer, CGL, and CTL layered in this order.
created a body. Examples 102 to 110 In Example 101, CTM was exemplified as shown in Table 11 below.
A photoreceptor was prepared in the same manner as in Example 101 except that a compound was used.
102 to 110 were created. Comparative Examples 21-22 As shown in Table 11 below, CTM was compared with Example 101.
Same as Example 101 except that compounds (1) to (2) were used.
A comparative photoreceptor was prepared in the same manner. Example 111 Using X-type metal-free phthalocyanine (X-Pc) in CGM
The intermediate layer -CGL- was prepared in the same manner as in Example 101 except that
A photoreceptor was prepared by sequentially laminating CTLs. Examples 112 to 120 In Example 111, CTM was exemplified as shown in Table 12 below.
A photoreceptor was prepared in the same manner as in Example 111 except that a compound was used.
112 to 120 were created. Comparative Examples 23-24 As shown in Table 12 below, CTM was compared with Example 111.
Same as Example 111 except that compounds (3) to (4) were used.
A comparative photoreceptor was prepared in the same manner. Example 121 Y-type oxytitanium phthalocyanine (TiO
Example 101, except that PC) (described above) was used.
In the same manner as above, the intermediate layer-CGL-CTL are sequentially stacked.
A photoreceptor was created. Examples 112 to 130 In Example 121, CTM was exemplified as shown in Table 13 below.
A photoreceptor was prepared in the same manner as in Example 121 except that a compound was used.
112 to 130 were created. Comparative Examples 25-26 As shown in Table 13 below, CTM was compared with Example 121.
Same as Example 121 except that compounds (5) to (6) were used.
A comparative photoreceptor was prepared in the same manner. Example 131 Except for using fluorenylidene-based azo CGM as CGM
, Intermediate layer-CGL-CTL in the same manner as in Example 101
A photoreceptor was created by sequentially laminating the following materials. Examples 132 to 140 In Example 131, CGM and CTM were determined as shown in Table 14 below.
The procedure was carried out in the same manner as in Example 131 except that the exemplified compound was used as
Photoreceptors 132 to 140 were created. Comparative Examples 27-28 As shown in Table 14 below, CTM was compared with Example 131.
Same as Example 131 except that compounds (1) to (2) were used.
A comparative photoreceptor was prepared in the same manner. [0161]
Table-1 Example No.
Photoreceptor No. CGM
CTM ──────────────
────────────────────
Example 1 Photoreceptor 1 Compound F1 −
23 Exemplified Compound <10> Example 2
Photoreceptor 2 Compound Example
Compound <2> Example 3 Photosensitivity
Body 3 Compound 〃 Exemplary compound〈4
> Example 4 Photoreceptor 4
Compound 〃 Exemplary compound <11>
Example 5 Photoreceptor 5 Compound
〃 Exemplary compounds <13> Examples
6 Photoreceptor 6 Compound F1-1
Exemplary compound <16> Example 7
Photoreceptor 7 Compound 〃 Exemplary compound
<17> Example 8 Photoreceptor 8
Compound 〃 Exemplary compound <19>
Example 9 Photoreceptor 9 Compound
Product F1-7 Exemplary compound <61> Implementation
Example 10 Photoreceptor 10 Compound F1 −
16 Exemplary Compound <110> Comparative Example 1
Comparative photoreceptor 1 Compound F1-23 Comparison
Compound <1> Comparative Example 2 Comparative photoreceptor
2 Compound 〃 Comparative compound〈2〉[0
162]
Table-2 Example No.
Photoreceptor No. CGM
CTM ──────────────
────────────────────
Example 11 Photoreceptor 11 Compound Q1
-3 Exemplary compound <10> Example 12
Photoreceptor 12 Compound 〃
Exemplary compound <6> Example 13
Photoreceptor 13 Compound Example
Compound <19> Example 14 Feeling
Light body 14 Compound 〃 Exemplary compound
<20> Example 15 Photoreceptor 1
5 Compound〃 Exemplary compound〈22
> Example 16 Photoreceptor 16
Compound〃 Exemplary compound〈30〉
Example 17 Photoreceptor 17
Compound〃 Exemplary compound〈35〉
Example 18 Photoreceptor 18 Compound
〃 Exemplary compound〈60〉 Implementation
Example 19 Photoreceptor 19 Compound
〃 Exemplary compound <65> Example 20
Photoreceptor 20 Compound
Exemplary compound <108> Comparative example 3
Comparative photoreceptor 3 Compound Comparison
Compound <3> Comparative example 4 Comparative photoreceptor 4
Compound 〃 Comparative compound〈4〉〈01
63]
Table-3 Example No. Photoreceptor N
o. CGM
CTM────────────────
────────────────────Example 21
Photoreceptor 21 Compound F1-23
Q1-3 Exemplary compound <10> Example 22
Photoreceptor 22 Compound
Exemplary compound <2> Example 23
Photoreceptor 23 Compound
Exemplary compound <4> Example 24
Photoreceptor 24 Compound
Exemplary compound <18> Example 25
Photoreceptor 25 Compound 〃
Exemplary compound <21> Example 26
Photoreceptor 26 Compound F1 -1 Q1
-3 Exemplary compound <33> Example 27
Photoreceptor 27 Compound
Exemplified compound <62> Example 28
Photoreceptor 28 Compound
Exemplary compound <70> Example 29
Photoreceptor 29 Compound F1 -7 Q1 -
3 Exemplified Compound <75> Example 30 Photosensitivity
Body 30 Compound F1 -16 Q1 -3
Exemplified Compound <98> Comparative Example 5 Comparative Photoreceptor 5
Compound F1-23 Q1-3 Comparative compound <5
〉Comparative Example 6 Comparative Photoreceptor 6 Compound
〃 Comparative compound〈6〉〈01
64]
Table-4 Example No. photosensitive
Body No. CGM
CTM──────────────
────────────────────────
Example 31 Photoreceptor 31 Compound
τ type metal-free lid Exemplary compound <8>
　　　　　　　　　　　　　　　　　　　　　　　　　
Russianine Example 32 Photoreceptor 3
2 Compound 〃
Exemplary compound <10> Example 33 Photoreceptor
33 Compound 〃
Exemplary compound <13> Example 34 Photosensitivity
Body 34 Compound 〃
Exemplary compound <20> Example 35
Light body 35 Compound 〃
Exemplary compound <25> Example 36
Photoreceptor 36 Compound 〃
Exemplary compound <88> Example 37
Photoreceptor 37 Compound
Exemplary compound <93> Example 38
Photoreceptor 38 Compound 〃
Exemplary compound <103 Example 39
Photoreceptor 39 Compound 〃
Exemplary compound <109> Example 4
0 Photoreceptor 40 Compound
〃 Exemplary compound〈114〉 Ratio
Comparative Example 7 Comparative Photoreceptor 7 Compound
〃 Comparative compound <1> Comparative example 8
Comparative photoreceptor 8 Compound
Comparative compound <2>0165
Table-5 Example No. photosensitive
Body No. CGM
CTM────────────────────
────────────── Example 41
Photoreceptor 41 Compound X-type metal-free lid
Exemplary compound <3>
Russianin
Example 42 Photoreceptor 42 Compound
〃 Exemplary compound <10>
Example 43 Photoreceptor 43 Compound
〃 Exemplary compound〈12
> Example 44 Photoreceptor 44 Compound
Product 〃 Exemplary compound〈1
7> Example 45 Photoreceptor 45
Compound 〃 Exemplary compound〈
23> Example 46 Photoreceptor 46
Compound 〃 Exemplary compound
<44> Example 47 Photoreceptor 47
Compound 〃 Exemplary compound
Object <51> Example 48 Photoreceptor 48
compound 〃 exemplification
Compound <63> Example 49 Photoreceptor 49
Compound Example
Compound <92> Example 50 Photoreceptor 50
Compound Example
Compound <101> Comparative Example 9 Comparative photoreceptor
9 Compound Comparison
Compound <3> Comparative Example 10 Comparative Photoreceptor 10
Compound 〃 Comparative compound
Object〈4〉〈0166〉
Table-6 Example No. photosensitive
Body No. CGM
CTM──────────────
──────────────────────Example
51 Photoreceptor 51 Compound Y-type O
Exemplary compound <1>
　　　　　　　　　　　　　　　　　　　　　　　　　
Muftalocyanine Example 52 Photoreceptor 52
Compound 〃
Exemplary compound <6> Example 53 Photoreceptor 5
3 Compound 〃
Exemplified compound <7> Example 54 Photosensitive
Body 54 Compound 〃
Exemplary compound <9> Example 55
Photoreceptor 55 Compound
Exemplary compound <10> Example 56
Photoreceptor 56 Compound
Exemplary compound <27> Example 57
Photoreceptor 57 Compound
Exemplary compound <38> Implementation
Example 58 Photoreceptor 58 Compound
〃 Exemplary compound〈40
〉Example 59 Photoreceptor 59 Compound
〃 Exemplary compounds
<55> Example 60 Photoreceptor 60
compound 〃 example
Compound <77> Comparative Example 11 Comparative Photoreceptor 11
Compound 〃 Ratio
Comparative compound <5> Comparative example 12 Comparative photoreceptor 12
Compound 〃 Ratio
Comparison compound <6>
Table-7 Example No.
Photoreceptor No. CGM
CTM ──────────────────
────────────── Example 61
Photoreceptor 61 Compound F2-6 Example
Compound <2> Example 62 Photoreceptor 6
2 Compound〃 Exemplary compound〈4〉
Example 63 Photoreceptor 63
Compound 〃 Exemplary compound〈6〉 Implementation
Example 64 Photoreceptor 64 Compound
〃 Exemplary compound <15> Example 65
Photoreceptor 65 Compound 〃
Exemplary compound <25> Example 66
Light substance 66 Compound 〃 Exemplary compound
<35> Example 67 Photoreceptor 67
Compound〃 Exemplary compound〈47〉
Example 68 Photoreceptor 68 Compound
Product 〃 Exemplary compound〈58〉 Implementation
Example 69 Photoreceptor 69 Compound F2 −
3 Exemplified Compound <69> Example 70
Photoreceptor 70 Compound F2-5 Exemplary compound
Product <80> Comparative Example 13 Comparative Photoreceptor 13
Compound F2-6 Comparative compound <1> Ratio
Comparative Example 14 Comparative Photoreceptor 14 Compound
Comparative compound <2>0168
Table-8 Example No.
Photoreceptor No. CGM
CTM ──────────────────
──────────────── Example 71
Photoreceptor 71 Compound F1-23
Exemplary compound (6) Example 72
Photoreceptor 72 Compound Example
Compound (8) Example 73 Photosensitivity
Body 73 Compound 〃 Exemplary compound
(11) Example 74 Photoreceptor 74
Compound 〃 Exemplary compound (20
) Example 75 Photoreceptor 75
Compound 〃 Exemplary compound (25)
Example 76 Photoreceptor 76 Compound
Product F1-1 Exemplary compound (35) Implementation
Example 77 Photoreceptor 77 Compound
〃 Exemplary compound (49) Example 78
Photoreceptor 78 Compound
Exemplary compound (102) Example 79
Photoreceptor 79 Compound F1-7 Illustration
Compound (133) Example 80 Photosensitivity
Structure 80 Compound F1-16 Exemplary compound (
293) Comparative Example 15 Comparative Photoreceptor 15
Compound F1-23 Comparative compound (1)
Comparative Example 16 Comparative Photoreceptor 16 Compound
〃 Comparative compound (2) 01
69]
Table-9 Example No. photosensitive
Body No. CGM
CTM ──────────────────
──────────────── Example 8
1 Photoreceptor 81 Compound Q1-3
Exemplary compounds (2) Example 82
Photoreceptor 82 Compound Example
Compound (5) Example 83 Feeling
Light substance 83 Compound 〃 Exemplary compound
(8) Example 84 Photoreceptor 8
4 Compound 〃 Exemplary compound (1
5) Example 85 Photoreceptor 85
Compound 〃 Exemplary compound (21
) Example 86 Photoreceptor 86
Compound 〃 Exemplary compound (33)
Example 87 Photoreceptor 87
Compound 〃 Exemplary compound (66)
Example 88 Photoreceptor 88
Compound 〃 Exemplary compound (80)
Example 89 Photoreceptor 89
Compound 〃 Exemplary compound (102)
Example 90 Photoreceptor 90
Compound 〃 Exemplary compound (163)
Comparative Example 17 Comparative Photoreceptor 17 Compound
〃 Comparative compound (3) Ratio
Comparative Example 18 Comparative Photoreceptor 18 Compound
Comparative compound (4)
Table-10 Example No. Feeling
Light body no. CGM
CTM────────────────
────────────────── Example 91
Photoreceptor 91 Compound F1-23
Q1-3 Exemplary compound (7) Example 92
Photoreceptor 92 compound
〃 Exemplary compound (11)
Example 93 Photoreceptor 93 Compound
〃 Exemplary compound (2
3) Example 94 Photoreceptor 94
compound 〃 exemplification
Compound (42) Example 95 Photoreceptor 9
5 Compound 〃
Exemplary compound (67) Example 96
Photoreceptor 96 Compound F1 -1 Q1 -3
Exemplary compound (88) Example 97
Photoreceptor 97 Compound
Exemplary compound (91) Example 98
Photoreceptor 98 compound
〃 Exemplary compound (107)
Example 99 Photoreceptor 99 Compound F1
-7 Q1 -3 Exemplary compound (123)
Example 100 Photoreceptor 100 Compound F1
-16 Q1 -3 Exemplary compound (191)
Comparative Example 19 Comparative Photoreceptor 19 Compound F1
-23 Q1 -3 Comparative compound (5) Ratio
Comparative Example 20 Comparative Photoreceptor 20 Compound
〃 Comparative compound (6) 0171
Table-11 Example No. Feeling
Light body No CGM
CTM────────────
────────────────────────
Example 101 Photoreceptor 101 Compound
τ type metal-free lid Exemplary compound (20)
　　　　　　　　　　　　　　　　　　　　　　　　　
Russianine Example 102
Photoreceptor 102 Compound
Exemplary compound (27) Example 103
Photoreceptor 103 Compound 〃
Exemplary compound (33) Example 10
4 Photoreceptor 104 Compound
〃 Exemplary compound (44) Implementation
Example 105 Photoreceptor 105 Compound
〃 Exemplary compound (53)
Example 106 Photoreceptor 106 Compound
〃 Exemplary compound (96
) Example 107 Photoreceptor 107
Compound 〃 Exemplary compound
(102) Example 108 Photoreceptor 108
compound 〃 exemplification
Compound (133) Example 109 Photoreceptor 1
09 Compound 〃
Exemplified compound (173) Example 110
Light body 110 Compound 〃
Exemplary compound (202) Comparative example 21
Comparative photoreceptor 21 Compound
Comparative compound (1) Comparative example 22
Comparative photoreceptor 22 Compound
Comparative compound (2)
Table-12 Example No. Feeling
Light body no. CGM
CTM──────────────────
────────────────Example 111
Photoreceptor 111 Compound X-type metal-free lid
Exemplary compound (2)
Russia
Example 112 Photoreceptor 112 Compound
〃 Exemplary compounds
(8) Example 113 Photoreceptor 113
Compound 〃 Exemplary compound
Item (14) Example 114 Photoreceptor 114
Compound Example
Compound (31) Example 115 Photoreceptor 1
15 Compound 〃
Exemplified compound (53) Example 116
Light body 116 Compound 〃
Exemplary compound (77) Example 117
Photoreceptor 117 Compound 〃
Exemplary compound (86) Example 118
Photoreceptor 118 Compound 〃
Exemplary compound (98) Example
119 Photoreceptor 119 Compound
〃 Exemplary compound (103)
Example 120 Photoreceptor 120 Compound
〃 Exemplary compound (2
17) Comparative Example 23 Comparative Photoreceptor 23 Compound
〃 Comparative compound (
3) Comparative Example 24 Comparative Photoreceptor 24 Compound
〃 Comparative compound (
4) 0173
Table-13 Example No. Feeling
Light body no. CGM
CTM──────────────
──────────────────────Example 1
21 Photoreceptor 121 Compound Y-type Oxygen
Exemplary compound (11)
　　　　　　　　　　　　　　　　　　　　　　　　　
Muftalocyanine Example 122 Photoreceptor 1
22 Compound 〃
Exemplary compound (35) Example 123
Photoreceptor 123 Compound 〃
Exemplary compound (43) Example 12
4 Photoreceptor 124 Compound
Exemplary compound (60)
Example 125 Photoreceptor 125 Compound
〃 Exemplary compounds
(105) Example 126 Photoreceptor 126
Compound Example
Compound (118) Example 127 Photoreceptor 1
27 Compound 〃
Exemplary compound (133) Example 128
Photoreceptor 128 Compound 〃
Exemplary compound (183) Example 12
9 Photoreceptor 129 Compound
Exemplary compound (228)
Example 130 Photoreceptor 130 Compound
〃 Exemplary compounds
(261) Comparative Example 25 Comparative Photoreceptor 25 Compound
thing 〃 comparison
Compound (5) Comparative Example 26 Comparative Photoreceptor 26
Compound 〃 Ratio
Comparison compound (6)
Table-14 Example No.
Photoreceptor No. CGM
CTM ────────────────
──────────────── Example 131
Photoreceptor 131 Compound F2-6 Example
Compound (3) Example 132
Light body 132 Compound 〃 Exemplary compound
(18) Example 133 Photoreceptor 1
33 Compound 〃 Exemplary compound (2
3) Example 134 Photoreceptor 134
Compound 〃 Exemplary compound (39)
Example 135 Photoreceptor 135
Compound 〃 Exemplary compound (48)
Example 136 Photoreceptor 136 Compound
〃 Exemplary compound (75) Implementation
Example 137 Photoreceptor 137 Compound
〃 Exemplary compound (91) Example 13
8 Photoreceptor 138 Compound
Exemplary compound (103) Example 139
Photoreceptor 139 Compound F2-3 Exemplification
Compound (119) Example 140 Photosensitivity
Body 140 Compound F2-5 Exemplary compound (1
37) Comparative Example 27 Comparative Photoreceptor 27
Compound F2-6 Comparative compound (1) Ratio
Comparative Example 28 Comparative Photoreceptor 28 Compound
Comparative Compound (2) [0175] (Evaluation Example 1) Copying machine U-Bi manufactured by Konica Co., Ltd.
Modified machine of x5076 (charging electrode changed to negative charging, exposure amount 4)
．． 65lux), and the linear speed was set to 240, 330, 4
40 mm/sec and 3 steps, 20,000 times charging and dew
The residual potential Vr was measured when light was repeatedly applied. The result is below
As shown in Tables 15 to 17, using the CTM of the present invention
The photoreceptor using the same compound had a higher linear velocity than the photoreceptor using the comparative compound.
It exhibits excellent high-speed performance with no large residual potential when
did. In addition, the initial blank paper potential (Vw) is shown in Tables 15 to 1 below.
It was as follows. (Evaluation Example 2) Same as that used in Evaluation Example 1
Using a modified Konica copier U-Bix5076
, 100,000 continuous copy tests using A4 recycled paper
went. The results are shown in Tables 18 to 20 below.
The photoreceptor using the compound of this patent has good image quality up to 100,000 cycles.
However, the photoreceptor using the comparative photoreceptor was used 20,000 to 30,000 times.
Several white spots appeared on the solid black part. In addition, Shiro Pochi's review
The value is determined by visually observing the number of white spots that occur on an A4 solid black image.
I counted. The results are shown in Tables 18 to 20 below. (Evaluation Example 3) Konica Digital Copy
U-Bix8028 was used at room temperature (25℃) and low temperature (
10°C), unexposed part potential VH, exposed part potential V
L was measured. The results are shown in Tables 21 to 24 below. (Evaluation Example 4) Same as that used in Evaluation Example 3
Konica's digital copy U-Bix8028,
Load the developing device and print out the image several times to make the white background of the copied image
The black spots in the area were evaluated. The results are in Tables 25 to 28 below.
Indicated. [0179] The evaluation of black spots was carried out using the image analysis device "OMM".
Black spots were detected using Nikon 300 model (manufactured by Shimadzu Corporation).
Measure the particle size and number of points, and find
Judgment was made based on the number of black spots per cm2. The criteria for black spot evaluation are as shown in the table below. [0180] Furthermore, if the result of black spot determination is ◎ or ○, it is practical.
However, △ may not be suitable for practical use, and × may not be suitable for practical use.
unsuitable for use. [0181]
Table-15
Initial: 20,000 repetitions at the following linear speed
Vr(v) after repetition
Blank paper potential Photoreceptor No. Vw
(v) 240mm/sec 330mm
/sec 440mm/sec
Repeat
repeat with return repeat with repeat ─
──────────────────────────
────── Photoreceptor 1 49
10 16
20 Photoreceptor 2
50 11
18 21
Photoreceptor 3 51
10 15
20 Photoreceptor 4 53
12 15
19 Photoreceptor 5
54 15
14 23
Photoreceptor 6 54 1
0 17
26 Photoreceptor 7 52
11 18
25 Photoreceptor 8
55 13
17 24
Photoreceptor 9 47 14
16
27 Photoreceptor 10 50
10 17
26 Comparative photoreceptor 1
68 16
43 79 Comparative feeling
Light body 2 72 19
49 85 0182]
Table-16
Initial: 20,000 repetitions at the following linear speed
Vr(v) after return
Blank paper potential Photoreceptor No. Vw
(v) 240mm/sec 330mm
/sec 440mm/sec
Repeat
repeat with return repeat with repeat ─
──────────────────────────
────── Photoreceptor 11 10
0 10 12
21 Photoreceptor 1
2 104 13
15 26
Photoreceptor 13 96
12 16
23 Photoreceptor 14
94 9 1
5 23 Photoreceptor
15 98 11
14 25
Photoreceptor 16 100
12 18
26 Photoreceptor 17
102 11
16 22 feeling
Light body 18 104 12
14 2
7 Photoreceptor 19 103
10 13
30 Photoreceptor 20
95 9
17 34 Comparison
Photoreceptor 3 116 12
43 83
Comparative photoreceptor 4 121
15 40
81 0183
Table-17
Initial: 20,000 repetitions at the following linear speed
Vr(v) after repetition
Blank paper potential Photoreceptor No. Vw
(v) 240mm/sec 330mm
/sec 440mm/sec
Repeat
repeat with return repeat with repeat ─
──────────────────────────
────── Photoreceptor 21 7
3 10 16
22 Photoreceptor 2
2 66 11
15 24
Photoreceptor 23 73
13 16
24 Photoreceptor 24
63 10
15 19 Photosensitivity
body 25 71 9
18 24
Photoreceptor 26 70
12 15
26 Photoreceptor 27
71 13
14 24 feeling
Light body 28 69 15
17 2
5 Photoreceptor 29 72
15 20
25 Photoreceptor 30
74 18
20 29 ratio
Comparison photoreceptor 5 83 17
41 79
Comparative photoreceptor 6 94
19 40
85 0184
Table-18 Photoreceptor No.
After 10,000 times After 50,000 times After 100,000 times
Number of white spots
Number of white dots Number of white dots ───
──────────────────────
Photoreceptor 1 0
0 0
Photoreceptor 2 0
0 0 Photoreceptor
3 0 1
2 Photoreceptor 4
0 0
0 Photoreceptor 5 0
0 0
Photoreceptor 6 0
0 0
Photoreceptor 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 2
0 38 0185]
Table-19 Photoreceptor No.
After 10,000 times After 50,000 times After 100,000 times
Number of white spots
Number of white dots Number of white dots ───
──────────────────────
Photoreceptor 11 0
0 0
Photoreceptor 12 0
0 0 feeling
Light body 13 0 0
2 Photoreceptor 14
0 0
2 Photoreceptor 15
0 1
2 Photoreceptor 16
0 0 0
Photoreceptor 17 0
0 0
Photoreceptor 18 0
0 0
Photoreceptor 19 0 1
2 Photoreceptor 2
0 0 0
0 Comparative photoreceptor 3
8 20
45 Comparative photoreceptor 4 6
25 49 0186]
Table-20 Photoreceptor No.
After 10,000 times After 50,000 times After 100,000 times
Number of white spots
Number of white dots Number of white dots ───
──────────────────────
Photoreceptor 21 0
0 0
Photoreceptor 22 0
0 1 feeling
Light body 23 0 0
0 Photoreceptor 24
0 0
0 Photoreceptor 25
0 1
2 Photoreceptor 26
0 0 0
Photoreceptor 27 0
0 0
Photoreceptor 28 0
0 0
Photoreceptor 29 0 1
3 Photoreceptor 3
0 0 0
0 Comparative photoreceptor 5
3 20
38 Comparative photoreceptor 6 3
18 36 0187]
Table-21
Room temperature (25℃)
Low temperature (10℃) Photoreceptor N
o.
VH(v) VL(v) VH(v) VL
(v) ────────────
──────────── Photosensitivity
Body 31 702 102 7
03 104 Photoreceptor
32 709 98 70
2 103 Photoreceptor 3
3 710 100 712
100 Photoreceptor 34
690 108 710
102 Photoreceptor 35
700 101 700
108 Photoreceptor 36
702 105 701
105 Photoreceptor 37
705 115 709
103 Photoreceptor 38
695 112 715
107 Photoreceptor 39
710 111 712 1
10 Photoreceptor 40 7
05 113 720 11
5 Comparative photoreceptor 7 702
120 683 170
Comparative photoreceptor 8 690 1
24 686 178 0188]
Table-22
Room temperature (25℃)
Low temperature (10℃) Photoreceptor N
o.
VH(v) VL(v) VH(v) VL
(v) ────────────
──────────── Photosensitivity
Body 41 703 108 7
03 104 Photoreceptor
42 704 102 70
3 105 Photoreceptor 4
3 707 105 700
103 Photoreceptor 44
706 102 712
99 Photoreceptor 45
710 115 706
106 Photoreceptor 46
720 104 715
105 Photoreceptor 47
718 100 710
111 Photoreceptor 48
705 112 715
109 Photoreceptor 49
702 110 706 1
10 Photoreceptor 50 7
15 115 707 11
3 Comparative photoreceptor 9 708
122 680 170
Comparative photoreceptor 10 709
123 690 178 0189]
Table-23
Room temperature (25℃) Low
Temperature (10℃) Photoconductor No.
．．
VH(v) VL(v) VH(v) VL(
v) ──────────────
────────── Photoreceptor
51 704 52 70
4 50 Photoreceptor 5
2 705 54 708
53 Photoreceptor 53
705 53 706
52 Photoreceptor 54
703 50 710
50 Photoreceptor 55
708 55 708
47 Photoreceptor 56
702 49 708
51 Photoreceptor 57
698 53 699
53 Photoreceptor 58
706 50 700
48 Photoreceptor 59 7
10 51 711 5
2 Photoreceptor 60 71
3 55 715 56
Comparative photoreceptor 11 715
62 685 91
Comparative photoreceptor 12 717
60 686 81 0190]
Table-24
Room temperature (25℃)
Low temperature (10℃) Photosensitive
Body No.
VH(v) VL(v) VH(v)
VL(v) ──────────
──────────────
Photoreceptor 61 699 102
700 104 feeling
Light body 62 701 107
702 105 Photosensitivity
Body 63 700 99 7
05 104 Photoreceptor
64 715 103 70
0 109 Photoreceptor 6
5 704 102 705
103 Photoreceptor 66
715 104 709
109 Photoreceptor 67
705 98 715
103 Photoreceptor 68
708 106 708
108 Photoreceptor 69
712 111 712
102 Photoreceptor 70
710 100 713
105 Comparative photoreceptor 13 71
8 123 689 153
Comparative photoreceptor 14 709
118 686 142 0191]
Table-25
20,000 copies 50,000 copies 1
After 00,000 copies of photoconductor used
after after
black spot format
Fixed Black spot determination Black spot determination ──
──────────────────────────
─── Photoreceptor 31
◎ ◎
◎ Photoreceptor 32
◎ ◎
◎ Photoreceptor 33
◎ ◎
◎ Photoreceptor 34
◎ ◎
◎ Photoreceptor 35
◎ ○
○ Photoreceptor 36
◎ ○
○ Photoreceptor 37
◎ ○
○ Photoreceptor 38
◎ ◎
○ Photoreceptor 39
◎ ○
○ Photoreceptor 40
◎ ○
○ Comparative photoreceptor 7 ○
△ ×
Comparative photoreceptor 8 ○
△ × [0192]
Table-26
20,000 copies 50,000 copies 1
After 00,000 copies of photoconductor used
after after
black spot format
Fixed Black spot determination Black spot determination ──
──────────────────────────
─── Photoreceptor 41
◎ ◎
◎ Photoreceptor 42
◎ ◎
◎ Photoreceptor 43
◎ ◎
◎ Photoreceptor 44
◎ ○
○ Photoreceptor 45
◎ ○
○ Photoreceptor 46
◎ ◎
◎ Photoreceptor 47
◎ ◎
◎ Photoreceptor 48
◎ ◎
○ Photoreceptor 49
◎ ◎
○ Photoreceptor 50
◎ ◎
○ Comparative photoreceptor 9 ○
△ ×
Comparative photoreceptor 10 ○
△ △【0
193]
Table-27
20,000 copies 50,000 copies 1
After 00,000 copies of photoconductor used
after after
black spot format
Fixed Black spot determination Black spot determination ──
──────────────────────────
─── Photoreceptor 51
◎ ◎
○ Photoreceptor 52
◎ ◎
◎ Photoreceptor 53
◎ ◎
◎ Photoreceptor 54
◎ ◎
◎ Photoreceptor 55
◎ ◎
◎ Photoreceptor 56
◎ ◎
◎ Photoreceptor 57
◎ ◎
○ Photoreceptor 58
◎ ◎
◎ Photoreceptor 59
◎ ◎
◎ Photoreceptor 60
◎ ◎
◎ Comparative photoreceptor 11 ○
△
× Comparative photoreceptor 12 ○
△ ×
[0194]
Table-28
20,000 copies 50,000 copies 1
After 00,000 copies of photoconductor used
after after
black spot format
Fixed Black spot determination Black spot determination ──
──────────────────────────
─── Photoreceptor 61
◎ ◎
◎ Photoreceptor 62
◎ ○
○ Photoreceptor 63
◎ ◎
◎ Photoreceptor 64
◎ ◎
◎ Photoreceptor 65
◎ ○
○ Photoreceptor 66
◎ ◎
◎ Photoreceptor 67
◎ ◎
◎ Photoreceptor 68
◎ ◎
◎ Photoreceptor 69
◎ ◎
◎ Photoreceptor 70
◎ ○
○ Comparative photoreceptor 13 ○
△
△ Comparative photoreceptor 14 ○
△ ×【
As mentioned above, electrophotographic sensitization based on the present invention
The body can be incorporated into a copier, printer, etc. and used repeatedly.
When using high sensitivity, white spots, black spots, fog, and low density can be detected.
A good image is obtained without any image defects or image defects.
It will be done. [0196] Furthermore, the electrophotographic photoreceptor according to the present invention has a high
Can be installed in high-speed copiers, printers, etc. and used repeatedly.
Also, the residual potential is small, and image defects and poor image quality do not occur.
A good image can be obtained. Next, Examples 71 to 140 and Comparative Example 15
When we performed the same evaluation as above for ~28, we found that
The results shown in Tables 29 to 42 were obtained. [0198]
Table-29
Initial: 20,000 repetitions at the following linear speed
Vr(v) after repetition
Blank paper potential Photoreceptor No. Vw
(v) 240mm/sec 330mm
/sec 440mm/sec
Repeat
repeat with return repeat with repeat ─
──────────────────────────
────── Photoreceptor 71 5
0 10 15
25 Photoreceptor 7
2 49 13
16 20
Photoreceptor 73 50
15 15
27 Photoreceptor 74
47 10
16 20 Photosensitivity
body 75 55 10
18 19
Photoreceptor 76 52
13 17
20 Photoreceptor 77
54 10
15 24
Photoreceptor 78 54 11
17
26 Photoreceptor 79 53
14 18
25 Photoreceptor 80
52 13
15 24
Comparative photoreceptor 15 72 18
44
78 Comparative photoreceptor 16 73
20 49
84 0199
Table-30
Initial: 20,000 repetitions at the following linear speed
Vr(v) after repetition
Blank paper potential Photoreceptor No. Vw
(v) 240mm/sec 330mm
/sec 440mm/sec
Repeat
repeat with return repeat with repeat ─
──────────────────────────
────── Photoreceptor 81 10
1 11 13
23 Photoreceptor 8
2 103 10
14 28
Photoreceptor 83 98
9 16
22 Photoreceptor 84
95 13 1
5 26 Photoreceptor
85 99 11
15 21
Photoreceptor 86 100
9 17
29 Photoreceptor 87
98 10
13 27 Photosensitivity
Body 88 102 12
16 26
Photoreceptor 89 94
10 15
30 Photoreceptor 90
100 12
16 29 Comparison
Photoreceptor 17 115 13
40 82
Comparative photoreceptor 18 120
16 40
80 0200]
Table-31
Initial: 20,000 repetitions at the following linear speed
Vr(v) after repetition
Blank paper potential Photoreceptor No. Vw
(v) 240mm/sec 330mm
/sec 440mm/sec
Repeat
repeat with return repeat with repeat ─
──────────────────────────
────── Photoreceptor 91 7
2 15 16
24 Photoreceptor 9
2 71 9
10 23
Photoreceptor 93 69
10 15
24 Photoreceptor 94
70 13 1
3 22 Photoreceptor
95 68 15
16 29
Photoreceptor 96 70
9 16
27 Photoreceptor 97
71 13
15 29 Photosensitivity
body 98 70 10
12 25
Photoreceptor 99 69
9 10
22 Photoreceptor 100
70 12
14 23 Comparison
Light body 19 83 16
41 77
Comparative photoreceptor 20 90
18 41
83 0201]
Table-32 Photoreceptor No.
After 10,000 times After 50,000 times After 100,000 times
Number of white spots
Number of white dots Number of white dots ───
──────────────────────
Photoreceptor 71 0
1 2
Photoreceptor 72 0
0 0 feeling
Light body 73 0 0
0 Photoreceptor 74
0 0
1 Photoreceptor 75
0 0
0 Photoreceptor 76
0 1 2
Photoreceptor 77 0
0 0
Photoreceptor 78 0
0 0
Photoreceptor 79 0 0
0 Photoreceptor 8
0 0 0
0 Comparative photoreceptor 15
5 21
40 Comparative photoreceptor 16 5
23 40 0202]
Table-33 Photoreceptor No.
After 10,000 times After 50,000 times After 100,000 times
Number of white spots
Number of white dots Number of white dots ───
──────────────────────
Photoreceptor 81 0
1 2
Photoreceptor 82 0
0 1 feeling
Light body 83 0 1
2 Photoreceptor 84
0 0
0 Photoreceptor 85
0 0
0 Photoreceptor 86
0 0 0
Photoreceptor 87 0
1 2
Photoreceptor 88 0
0 0
Photoreceptor 89 0 0
0 Photoreceptor 9
0 0 0
0 Comparative photoreceptor 17
10 21
43 Comparative photoreceptor 18
8 18 46 0203]
Table-34 Photoreceptor No.
After 10,000 times After 50,000 times After 100,000 times
Number of white spots
Number of white dots Number of white dots ───
──────────────────────
Photoreceptor 91 0
0 1
Photoreceptor 92 0
1 2 feeling
Light body 93 0 0
0 Photoreceptor 94
0 0
0 Photoreceptor 95
0 0
0 Photoreceptor 96
0 0 1
Photoreceptor 97 0
1 2
Photoreceptor 98 0
0 0
Photoreceptor 99 0 0
0 Photoreceptor 1
00 0 0
0 Comparative photoreceptor 19
3 21
39 Comparative photoreceptor 20 4
19 35 0204]
Table-35
Room temperature (25℃)
Low temperature (10℃) Photoreceptor N
o.
VH(v) VL(v) VH(v) VL
(v) ────────────
──────────── Photosensitivity
Body 101 703 101 7
04 103 Photoreceptor
102 700 103 70
3 102 Photoreceptor 1
03 709 99 710
100 Photoreceptor 10
4 710 110 705
103 Photoreceptor 105
700 100 715
107 Photoreceptor 106
703 111 712
105 Photoreceptor 107
698 105 720
115 Photoreceptor 108
699 100 705
104 Photoreceptor 109
702 105 707 1
10 Photoreceptor 110 7
05 104 703 11
3 Comparative photoreceptor 21 703
121 682 177
Comparative photoreceptor 22 698
123 685 173 0205]
Table-36
Room temperature (25℃)
Low temperature (10℃) Photoreceptor N
o.
VH(v) VL(v) VH(v) VL
(v) ────────────
──────────── Photosensitivity
Body 111 704 107 7
03 105 Photoreceptor
112 709 105 70
5 111 Photoreceptor 1
13 706 110 710
105 Photoreceptor 11
4 710 104 715
103 Photoreceptor 115
705 103 710
106 Photoreceptor 116
713 100 706
105 Photoreceptor 117
704 105 709
99 Photoreceptor 118
710 112 715
107 Photoreceptor 119
705 103 710 1
08 Photoreceptor 120 7
03 105 708 11
1 Comparative photoreceptor 23 709
120 683 171
Comparative photoreceptor 24 710
122 689 179 0206]
Table-37
Room temperature (25℃)
Low temperature (10℃) Photoreceptor N
o.
VH(v) VL(v) VH(v) VL
(v) ────────────
──────────── Photosensitivity
Body 121 705 51 7
06 45 Photoreceptor
122 711 49 70
7 53 Photoreceptor 1
23 705 50 708
47 Photoreceptor 12
4 700 55 705
56 Photoreceptor 125
699 58 700
53 Photoreceptor 126
705 53 699
48 Photoreceptor 127
711 54 695
50 Photoreceptor 128
710 49 700
52 Photoreceptor 129
706 50 715
50 Photoreceptor 130 7
05 52 711 5
0 Comparative photoreceptor 25 717
63 680 98
Comparative photoreceptor 26 718
65 679 85 0207]
Table-38
Room temperature (25℃)
Low temperature (10℃) Photoreceptor N
o.
VH(v) VL(v) VH(v) VL
(v) ────────────
──────────── Photosensitivity
Body 131 700 102 7
02 103 Photoreceptor
132 700 101 70
0 102 Photoreceptor 1
33 715 108 713
109 Photoreceptor 13
4 705 103 705
103 Photoreceptor 135
709 108 700
108 Photoreceptor 136
708 110 705
104 Photoreceptor 137
703 106 710
105 Photoreceptor 138
710 103 700
103 Photoreceptor 139
705 110 708 1
02 Photoreceptor 140 7
10 105 711 10
5 Comparative photoreceptor 27 716
122 690 150
Comparative photoreceptor 28 720
119 686 143 0208]
Table-39
20,000 copies 50,000 copies 1
After 00,000 copies of photoconductor used
after after
black spot format
Fixed Black spot determination Black spot determination ──
──────────────────────────
─── Photoreceptor 101
◎ ◎
◎ Photoreceptor 102
◎ ◎
◎ Photoreceptor 103
◎ ◎
◎ Photoreceptor 104
◎ ◎
○ Photoreceptor 105
◎ ◎
◎ Photoreceptor 106
◎ ○
○ Photoreceptor 107
◎ ◎
◎ Photoreceptor 108
◎ ○
○ Photoreceptor 109
◎ ◎
◎ Photoreceptor 110
◎ ◎
○ Comparative photoreceptor 21 ○
△
× Comparative photoreceptor 22 ○
△ ×
[0209]
Table-40
20,000 copies 50,000 copies
Photoconductor used for 100,000 copies
after after after
The black spot
Point judgment Black spot judgment Black spot judgment
──────────────────────────
───── Photoreceptor 111
◎ ◎
◎ Photoreceptor 112
◎ ○
○ Photoreceptor 113
◎ ○
○ Photoreceptor 114
◎ ◎
◎ Photoreceptor 115
◎ ◎
◎ Photoreceptor 116
◎ ◎
◎ Photoreceptor 117
◎ ◎
○ Photoreceptor 118
◎ ○
○ Photoreceptor 119
◎ ◎
◎ Photoreceptor 120
◎ ◎
◎ Comparative photoreceptor 23
○ △
× Comparative photoreceptor 24 ○
△
×0210]
Table-41
20,000 copies 50,000 copies 1
After 00,000 copies of photoconductor used
after after
black spot format
Fixed Black spot determination Black spot determination ──
──────────────────────────
─── Photoreceptor 121
◎ ◎
◎ Photoreceptor 122
◎ ◎
○ Photoreceptor 123
◎ ◎
◎ Photoreceptor 124
◎ ◎
◎ Photoreceptor 125
◎ ◎
○ Photoreceptor 126
◎ ◎
◎ Photoreceptor 127
◎ ◎
◎ Photoreceptor 128
◎ ◎
◎ Photoreceptor 129
◎ ◎
◎ Photoreceptor 130
◎ ◎
◎ Comparative photoreceptor 25 ○
△
× Comparative photoreceptor 26 ○
△ × [0211]
Table-42
20,000 copies 50,000 copies
Photoconductor used for 100,000 copies
after after after
The black spot
Point judgment Black spot judgment Black spot judgment
──────────────────────────
───── Photoreceptor 131
◎ ◎
◎ Photoreceptor 132
◎ ○
○ Photoreceptor 133
◎ ◎
◎ Photoreceptor 134
◎ ◎
◎ Photoreceptor 135
◎ ◎
◎ Photoreceptor 136
◎ ○
○ Photoreceptor 137
◎ ◎
◎ Photoreceptor 138
◎ ○
○ Photoreceptor 139
◎ ◎
◎ Photoreceptor 140
◎ ◎
◎ Comparative photoreceptor 27
○ △
△ Comparative photoreceptor 28 ○
△
×0212 Example 141 Next, unlike the above example, the present invention was
An example in which the present invention is applied to luminescence will be described. [0213] Transparent electrode (ind.
500 as a charge injection layer on top of the (dium-tin oxide layer)
Exemplified compound <23> was deposited to a thickness of Å, and then 8-
Using quinolinol A1 complex (Alq3) as an organic fluorescent layer
The negative electrode was deposited to a thickness of 600 Å on top of that.
A magnesium/silver alloy was then deposited. [0214] The emission characteristics of the obtained organic thin film EL device were investigated.
As a result, the light emission of 0.04mW/cm2 is 4mA/
Obtained in cm2. The emitted light color was yellow-green. [0215] [0216]
Table-43 No.
R1 (R2)n
R3a R3b────
──────────────────────────
── <1> 2-Br H(n
=0)H
H <2> 3-Br
H( 〃) 〃
〃〈3〉 4-Br
H( 〃) 〃
〃〈4〉 2-F
H( 〃) 〃
〃〈5〉 3-F
H( 〃) 〃
〃〈6〉 4
-F H (〃)
〃 〃〈7〉
2-I H (〃)
〃 〃〈8〉
3-I H (〃)
〃 〃〈9
〉 4-I H (〃)
〃 〃
<10> 2-Cl H ( )
〃
〃〈11〉 3-Cl H(
〃) 〃
〃〈12〉 2-CN
H( 〃) 〃
〃〈13〉 3-CN
H( 〃) 〃
〃〈14〉 2-Br
4-CH3 〃
〃〈15〉 4
-Br2-CH3
〃 〃 〈16〉
4-Br 3-CH3
〃 〃 〈
17> 2-Cl 4-CH3
〃
〃〈18〉 2-Cl 5-C
H3 〃
〃〈19〉2-Cl
6-CH3 〃
〃〈20〉 3-Cl
2-CH3 〃
〃 〈21〉 3-
Cl4-CH3
〃 〃 〃〈22〉
5-Cl2-CH3
〃 〃〈2
3> 2-F 6-CH3
〃 〃
<24> 3-F 2-CH
3 〃
〃〈25〉 3-F
4-CH3 〃
〃〈26〉 4-F
2-CH3 〃
〃〈27〉 5-F
2-CH3
〃 〃〈28〉
2-Cl 4-Cl
〃 〃〈29
〉 2-Cl 3-CH3,4-C
l 〃 〃
<30> 2-Cl 3-CH3
,6-Cl 〃
〃〈31〉 3-Cl 3
-CH3,6-CH3 〃
〃〈32〉 3-Cl
4-Cl 〃
〃〈33〉 3-Cl
2-CH3 〃
〃〈34〉
2-Br 4-Br
〃〃〃〈35〉
2-Br 5-CH3
〃 〃
<36> 2-F 3,4,5,
6-F 〃
〃〈37〉 2-Cl 3,
4,5,6-Cl〃
〃〈38〉 2-Br
4-C2H5 〃
〃〈39〉 4-Br
4-C3H7 〃
〃 〈40〉 2
-I4-CH3
〃〃〃〈41〉
4-I 2-C2H5
〃 〃 〈
42> 2-CN 4-CH3
〃
〃〈43〉 2-CN 4-C
4H9 〃
〃〈44〉 3-CN
4-CH3 〃
〃〈45〉 2-Br
H (n=0) 4-C
H3 〃 〈46〉 3
-Br H(〃)
〃 〃 〃〈47〉
4-Br H(〃)
〃 〃〈48
〉 2-F H (〃)
〃 〃
<49> 3-F H ( )
〃
〃〈50〉 4-F H(
〃) 〃
〃〈51〉 2-I
H( 〃) 〃
〃〈52〉 3-I
H( 〃) 〃
〃〈53〉 4-I
H( 〃) 〃
〃 〈54〉 2-
Cl H(〃)
〃〃〃〈55〉
3-ClH(〃)
〃 〃〈56〉
2-CN H(〃)
〃 〃 〈
57〉 3-CN H(〃)
〃 〃
<58> 2-Br 4-CH
3 〃
〃〈59〉 4-Br
2-CH3 〃
〃〈60〉 4-Br
3-CH3 〃
〃〈61〉 2-C
l4-CH3
〃 〃 〈62〉
2-Cl 5-CH3
〃 〃〈63
〉 2-Cl 6-CH3
〃 〃
<64> 3-Cl 2-CH3
〃
〃〈65〉 3-Cl 4
-CH3 〃
〃〈66〉5-Cl
2-CH3 〃
〃〈67〉 2-F
6-CH3 〃
〃〈68〉
3-F 2-CH3
〃 〃〈69〉
3-F 4-CH3
〃 〃
<70> 4-F 2-CH3
〃
〃〈71〉 5-F 2-
CH3 〃
〃〈72〉2-Cl
4-Cl 〃
〃〈73〉2-Cl
3-CH3,4-Cl 〃
〃 〈74〉 2
-Cl5-CH3,4-Cl
〃 〃〈75〉
2-Cl 6-CH3,4-Cl
〃 〃 〈
76> 3-Cl 5-Cl
〃
〃〈77〉 3-Cl 2-C
H3,5-Cl 〃
〃〈78〉2-Br
4-Br 〃
〃〈79〉2-Br
5-CH3,4-Br 〃
〃 〈80〉 2-
F 3,4,5,6-F
〃 〃 〃〈81〉
2-Cl 3,4,5,6-Cl
〃 〃〈8
2> 2-Br 4-C2H5
〃 〃
<83> 4-Br 3-C3
H7 〃
〃 〈84〉 2-I
4-CH3 〃
〃〈85〉 4-I
2-C2H5 〃
〃〈86〉 2-C
N4-CH3
〃 〃 〃〈87〉
2-CN 4-C4H9
〃 〃〈88
〉 3-CN 4-CH3
〃 〃
<89> 2-Br H (n=0
) 4-Cl
〃〈90〉 3-Br
H( 〃) 〃
〃〈91〉4-Br
H( 〃) 〃
〃〈92〉 2-F
H( 〃) 〃
〃〈93〉 3-
F H (〃)
〃〃〃〈94〉
4-F H (〃)
〃 〃〈95〉
2-I H (〃)
〃 〃 〈
96〉 3-I H(〃)
〃 〃
<97> 4-I H( 〃
) 〃
〃〈98〉2-ClH
( 〃) 〃
〃〈99〉3-Cl
H( 〃) 〃
〃〈100〉 2-CN
H( 〃) 〃
〃〈101〉 3-C
N H ( 〃) 〃
〃〈 102〉
4-ClH(〃)
4-N(C2H5)2 4-CN〈 1
03〉 4-Cl H(〃)
4-N(CH2-Ph)2
4-CN〈104〉 4-Br
H( 〃) 4-N(CH3)(CH2
-Ph) 4-CN〈105〉 4-CN
H( 〃) 4-
OC2H5 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-C
l2-CH3
4-CH3 4-CH3 < 1
09> 3-Cl 4-CH3
2-CH3
H〈110〉5-Cl2
-CH3 3-CH3
H〈111〉 2-F
5-CH3 4-O
CH3 4-OCH3〈112〉
3-F 2-CH3
2,4-di-CH3H
<113> 3-F 4-CH
3 2,5-di-CH3
H〈114〉 4-F
2-CH3 3,4-di-C
H3 H〈115〉 5-F
2-CH3
4-CH3 4-CH3 < 1
16> 2-Cl 4-Cl
2-CH3
H〈117〉2-Cl3
-CH3,4-Cl3-CH3
H〈118〉2-Cl
5-CH3,4-Cl2,4-d
i-CH3H〈119〉
2-Cl 6-CH3,4-CH3
4-OCH3H〈12
0> 3-Cl 5-Cl
2-Cl
3-Br〈121〉3-Cl
2-CH3,5-Cl 4-Cl
H〈122〉2-Br
4-Br 4-N(C
H3) (C2H5) H〈123〉
2-Br 5-CH3,4-Br
4-C3H7 H〈 1
24> 2-F 3, 4, 5, 6
-F 4-F
4-CH3 <125> 2-Cl
3,4,5,6-Cl4-Br
H〈126〉 2-
Br4-C2H5
4-I H〈127〉
4-Br 4-C3H7
4-CNH
<128> 2-I 4-CH
3 2,4-di-Cl
2-Cl〈129〉4-I
2-C2H5 4-N(CH
3) 2 H〈130〉 2
-CN4-CH32,
3,4,5,6 Per-F H〈131
〉 2-CN 4-C4H9
4-C4H9 3
-CN〈132〉 3-CN 4
-CH3 3-OCH3
3-OCH3 <133> 2-
CF3H (n=0)
4-OCH3H〈134〉
3-CF3H (〃)
2-C2H5 4-C
H3 <135> 4-CF3 H
(〃) 2,4-di-CH3
H〈136〉3-CN
4-CN 2-CH3
3-CH3〈137〉
3-CN 5-CN
3,5-di-CH3H〈
138〉 2-CN 4-CN
3,4-di-CH3
〃〈139〉3-Cl
4-Cl2,4-di-CH3
〃〈140〉 2-Cl
4-Cl, 3-F 4-C3H
7〃〃〈141〉 3
-Br 5-Br
2-CH3〃〃〃〈142〉
2-Br 3-CH3
4-OCH3〃〃〃〃〃〃〃〃〃
143> 4-Br 2-CH3
3-CH3
3-CH3 <144> 2-Cl
5-CH3 2-CH
3 4-CH3 <145>
2-Cl 6-CH3
3-CH3 4-
CH3 <146> 2-CN
4-CH3 2-CH3
3-CH3 <147> 3
-CN4-CH3
2-CH3 3-CH3 <
148> 3-Cl 2-CH3
2-CH3
3-CH3 <149> 3-Cl
4-CH3 4-OC
H3 H〈150〉
2-CN 4-CH3
4-N(CH3)2 〃〃〃〃〃〃〃〃〃〃〃〃〃〃〃〃〃〃
〉 3-CN 4-CH3
4-N(CH3)2 〃
<152> 2-Cl 3-CH3,
4-Cl 4-CN
〃〃〉 153〉 2-CF3
3-CH3 3-CN
〃〃〉 154〉 2-Br
4-CH3,3-Br4-C
H3〃〃〈155〉
2-F 3-Cl
4-CH3 3-Br,2-F
<156> 2-CN H (n=
0) 4-CF3
H〈157〉3-Cl
H(〃) 2-CF3
[Chemical Formula 23] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 220] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 27] [Chemical Formula 29] [Formula 30] [Formula 31] [Formula 31] [Formula 32] [Formula 32] [Formula 32]
Table 44 No. R
11 R12
R13a R13b ──────
──────────────────────────
──────(1) 2-OCH3
H (n=0) 2-OCH3
H (2)
3-OCH3H(〃)
2-OCH3 〃(3
) 2-N(C2H5)2H(
〃) 2-OCH3
〃(4) 3-N(C2H5
)2H( ) 3-OC2H
5 〃(5) 2
-OCH3 3-CH3
4-CH3〃(6
) 3-OCH3 2-
CH3 〃
〃(7) 4-OCH3
2-CH3 〃
〃(8) 5
-OCH3 2-CH3
〃 〃(9)
6-OCH3 2-C
H3 〃
〃(10) 2-N(C2H5)2
3-CH3 〃
〃(11) 3-N(
C2H5)2 2-CH3
〃 〃(12)
4-N(C2H5)2 2-CH
3 〃
〃(13) 5-N(C2H5)2
2-CH3 〃
〃(14) 6-N(C
2H5)2 2-CH3
〃 〃(15)
2-OC2H5 3-CH3
〃
〃(16) 3-OC2H5
2-CH3 〃
〃(17) 4-OC
2H5 2-CH3
〃 〃(18)
5-OC2H5 2-CH3
〃
〃(19) 6-OC2H5
2-CH3 〃
〃(20) 2-OCH
3H (n=0)
H〃(21)
3-OCH3H(〃)
〃
〃(22) 2-N(C2H5)2
H( 〃) 〃
〃(23) 3-N(C2H5)
2 H( 〃) 〃
〃(24)
2-OCH3 5-Cl
〃 〃(2
5) 3-OCH3 4-
C2H5 〃
〃(26) 4-OCH3
2-C3H7 〃
〃(27) 3
-OCH3 4-Cl
〃 〃(28
) 6-OCH3 2,4-
di-Cl 〃
〃(29) 2-N(C2H5)2
4-C2H5 〃
〃(30) 3-N(
C2H5)25-CN
〃 〃(31)
4-N(C2H5)2 2-B
r 〃
〃(32) 5-N(C2H5)2
3-CN〃
〃(33) 6-N(C
2H5)2 2,4-di-CH3
〃 〃(34)
2-OC2H5 4-C2H
5 〃
〃(35) 3-OC2H5
2-C2H5 〃
〃(36) 4-OC
2H5 2-CN
〃 〃(37)
5-OC2H5 3-Br
〃
〃(38) 6-OC2H5
2,4-di-CH3
〃(39) 2-OCH
3 H (n=0) 4
-N(CH3)2H (40)
3-OCH3H(〃)
4-N(C2H5)2
〃(41) 2-N(C2H5)2
H(〃) 4-OC2H5
〃(42) 3-N(C2
H5) 2 H( 〃) 4-N
(CH2-Ph)2 〃(43)
2-OCH3 4-CH3
4-N(CH3)(CH2-Ph)
〃(44) 3-OCH3
5-CH3 4-C2H5
〃(45) 4-O
CH32-C4H9
4-C2H5〃(46)
5-OCH3 3-C2
H5 4-CN
〃(47) 2-OCH3
4-C2H5 4-I
〃(48) 2-N
(C2H5)2 4-C2H5
4-C2H5〃(4
9) 3-N(C2H5)2 4-
C3H7 4-Br
〃(50) 4-N(C2H5)2
2-C3H7 4-
I〃(51) 5
-N(C2H5)2 3-C2H5
4-Cl 〃
(52) 6-N(C2H5)2 2,4
-di-C2H5 4-F
〃(53) 2-OC2H
5 4,6-di-C2H5
4-Cl〃(54)
3-OC2H5 5-F
4-C3H7
〃(55) 4-OC2H5 2
,6-di-CN4-C2H5
〃(56) 5-OC
2H5 3-I
4-CN〃(57)
2-OC2H5 4-Cl
2-CH3
〃(58) 2-OCH3
H(n=0) 4-N(CH3
)2 4-CH3 (59)
3-OCH3H(〃)
4-N(C2H5)2 〃(
60) 2-N(C2H5)2H
(〃) 4-OC2H5
〃(61) 3-N(C2H5)2
H( 〃) 4-N(CH2
-Ph)2〃(62)
2-OCH3 4-CH3
4-N(CH3)(CH2-Ph) 〃(
63) 3-OCH3 5
-CH34-C2H5
〃(64) 4-OCH3
2-C4H9 4-C
2H5〃(65)
5-OCH3 3-C2H5
4-CN
〃(66) 2-OCH3
4-C2H5 4-I
〃(67) 2-N(C2H
5) 2 4-C2H5 4
-C2H5〃(68)
3-N(C2H5)2 4-C3H7
4-Br
〃(69) 4-N(C2H5)2
2-C3H7 4-I
〃(70) 5-N(C
2H5)2 3-C2H5
4-Cl〃(71)
6-N(C2H5)2 2,4-di-
C2H5 4-F
〃(72) 2-OC2H5
4,6-di-C2H5 4-Cl
〃(73) 3
-OC2H5 5-F
4-C3H7〃(7
4) 4-OC2H5 2,6-d
i-CN4-C2H5
〃(75) 5-OC2H5
3-I 4-
CN〃(76)
2-OC2H5 4-Cl
2-CH3 〃
(77) 2-OCH3
H (n=0) 4-CH3
2-Br (78) 3-O
CH3 H (〃)
4-CH3 2-C2H5(7
9) 2-N(C2H5)2H(
〃) 4-CH3
H (80) 3-N(C2H5)2
H(〃) 2-CH
3 4-Br (81)
2-OCH3 4-CH3
4-C2H5
2-CN (82) 3-OCH3
4-C2H5 4-Cl
2-I (83)
4-OCH3 2-C3H7
〃H (
84) 3-OCH3 4
-Cl 〃
H (85) 6-OCH3
2,4-di-Cl
〃H (86)
2-N(C2H5)2 4-C2H5
〃 4-
CH3(87) 3-N(C2H5)2
5-CN〃
4-CH3(88) 4-N
(C2H5)2 2-Br
〃H (8
9) 5-N(C2H5)2 3-
CN 〃
〃(90) 6-N(C2H5)2
2,4-di-CH3
〃(91) 2
-OC2H5 4-C2H5
〃 〃(92
) 3-OC2H5 2-C
2H5 〃
〃(93) 4-OC2H5
2-CN〃
〃(94) 5-
OC2H5 3-Br
〃 〃(95)
6-OC2H5 2,4-di-
CH3 〃
〃(96) 2-OCH3
H (n=0) 2-OCH3
4-N(CH3)2(97)
3-OCH3H(〃)
2-OCH3
4-Br (98) 2-N(C2H5)2
H(〃) 2-OCH3
4-F(99) 3-
N(C2H5)2H( 〃)
3-OC2H5 4-Cl
(100) 2-OCH3
3-CH3 4-CH3
2,3,4,tri-Cl(101)
3-OCH3 2-CH3
〃 2,4-d
i-Cl (102) 4-OCH3
2-CH3 〃
2,3,4,tri-F (103)
5-OCH3 2-CH3
〃
4-CH3(104) 6-OCH3
2-CH3 〃
〃(105) 2-N
(C2H5)2 3-CH3
〃 〃(10
6) 3-N(C2H5)2 2-C
H3 〃
〃(107) 4-N(C2H5)2
2-CH3 〃
〃(108) 5-N(
C2H5)2 2-CH3
〃 〃(109
) 6-N(C2H5)2 2-CH
3 〃
〃(110) 2-OC2H5
3-CH3 〃
〃(111) 3-O
C2H5 2-CH3
〃 〃(112)
4-OC2H5 2-CH3
〃
〃(113) 5-OC2H5
2-CH3 〃
〃(114) 6-OC
2H5 2-CH3
〃 〃(115)
2-N(CH3)2 3-CH3
〃
2-CH3(116) 3-N(CH3)2
2-CH3 〃
2-CH3(117)
4-N(CH3)2 2-CH3
〃 2-N(C
H3)2(118) 5-N(CH3)2
2-CH3 〃
2-CH3(119) 6
-N(CH3)2 2-CH3
〃 2-N(CH
3) 2(120) 2-N(CH3)2
3-CH3 〃
H (121) 3-N(
CH3)2 2-CH3
〃 〃(122)
4-N(CH3)2 2-CH3
〃
〃(123) 5-N(CH3)2
2-CH3 〃
〃(124) 6-N(C
H3)2 2-CH3
〃 〃(125)
2-N(CH3)2H(n=0)
H
〃(126) 2-N(CH3)2
H (n=0) 4-CH3
〃(127) 2-O
CH3 4-OCH3
H〃(128
) 3-N(CH3)2H(n=
0) 4-CH3
〃(129) 3-OCH3
4-OCH3H
〃(130) 4-
N(CH3)2H(n=0)
4-CH3〃(1
31) 4-OC2H5H(
〃) 4-CH3
〃(132) 4-OC2H5
H(〃) 3-CH
3 (133) 4-
OC2H5 H(〃)
2-CH3〃(13
4) 2-OC2H5H(
〃) 4-CH3
〃(135) 2-OCH3
5-OCH3H
〃(136) 4-
N(CH3)2H(n=0)
4-Cl 〃(1
37) 4-N(CH3)2H(
n=0) 4-Br
〃(138) 2-N(CH3)2
4-N(CH3)2H
〃(139)
4-N(CH3)2H (n=0)
2,4-di-Cl〃
(140) 〃
〃 4-N(C2H5)2
4-N(C2H5)2 (141)
〃 〃
4-N(CH3)2 4-N(CH3)
2 (142) 〃
〃H
4-N(C2H5)2 (143)
〃 〃
〃 3-N(C2H5
)2 (144) 〃
〃 〃
2-N(C2H5)2 (145)
〃 〃
4-OCH3 4-OCH3
(146) 〃
〃H
4-OCH3 (147) 〃
〃
〃 2-CH3 (148)
〃 〃
〃 3
-CH3 (149) 〃
〃 〃
H (150) 3-N(C
2H5) 2 〃 4
-N(C2H5)2 4-N(C2H5)2
(151) 〃
〃 4-N(CH3)2
4-N(CH3)2(152)
〃 〃
H4-N(C2H5)
2 (153) 〃
〃 〃
3-N(C2H5)2 (154)
〃 〃
〃 2-N(C2H5
)2 (155) 〃
〃 4-OCH3
4-OCH3 (156)
〃 〃
H4-OCH3 (1
57) 〃 〃
〃
2-CH3 (158) 〃
〃 〃
3-CH3 (159)
〃 〃
〃 4-CH3
(160) 〃
〃 〃
4-Cl (161) 2-N(C2H
5) 2 〃 4-N
(C2H5)2 4-N(C2H5)2 (
162) 〃 〃
4-N(CH3)2
4-N(CH3)2(163)
〃
H4-N(C2H5)2
(164) 〃
〃 〃
3-N(C2H5)2 (165)
〃 〃
〃 2-N(C2H5)2
(166) 〃
〃 4-OCH3
4-OCH3 (167) 〃
〃
H2-CH3(168
) 〃 〃
〃
3-CH3(169) 〃
〃 〃
4-Cl (170) 3-
OCH3 4,5-OCH3
4-N(C2H5)2 4-N(C2
H5) 2 (171) 〃
〃 4-N(CH3)
2 4-N(CH3)2(172)
〃 〃
H4-N(C
2H5)2 (173) 〃
〃 〃
3-N(C2H5)2 (174)
〃 〃
〃 2-N(
C2H5)2 (175) 〃
〃 4-OCH3
4-OCH3 (176)
〃 〃
H4-OCH
3 (177) 〃
〃 〃
2-CH3 (178) 〃
〃
〃 3-CH3 (179)
〃 〃
〃 4
-CH3 (180) 〃
〃 〃
H (181) 〃
〃
〃 4-Cl (182)
2-OCH3 4-OCH3
4-N(C2H5)2
4-N(C2H5)2 (183)
〃 4-
N(CH3)2 4-N(CH3)2(1
84) 〃 〃
H
4-N(C2H5)2 (185)
〃
〃 3-N(C2H5)2
(186) 〃
〃 〃
2-N(C2H5)2 (187)
〃 〃
4-OCH3 4-OCH3 (1
88) 〃 〃
H
4-OCH3 (189) 〃
〃 〃
2-CH3 (190)
〃 〃
〃 3-CH
3 (191) 〃
〃 〃
4-CH3 (192) 〃
〃
〃 4-Cl (193)
〃 5-OCH3
4-N(C2H5)2 4-
N(C2H5)2 (194) 〃
〃 4-N(
CH3)2 4-N(CH3)2(195
) 〃 〃
H 4
-N(C2H5)2 (196) 〃
〃
〃 3-N(C2H5)2 (1
97) 〃 〃
〃
2-N(C2H5)2 (198)
〃 4-
OCH3 4-OCH3 (199
) 〃 〃
H 4
-OCH3 (200) 〃
〃 〃
2-CH3 (201)
〃 〃
〃 3-CH3 (202) 〃
〃 〃
4-CH3 (203) 〃
〃 〃
4-Cl (204)
3-OCH3 4-OCH3
4-N(C2H5)2 4-
N(C2H5)2 (205) 〃
〃 4-N(
CH3)2 4-N(CH3)2(206
) 〃 〃
H 4
-N(C2H5)2 (207) 〃
〃
〃 3-N(C2H5)2 (2
08) 〃 〃
〃
2-N(C2H5)2 (209)
〃 4-
OCH3 4-OCH3 (210
) 〃 〃
H 4
-OCH3 (211) 〃
〃 〃
2-CH3 (212)
〃 〃
〃 3-CH3(
213) 〃 〃
〃
4-CH3(214) 〃
〃 〃
4-Cl (215)
2-OCH3 5-CH3
4-N(C2H5)2 4-N
(C2H5)2 (216) 〃
〃 4-N(C
H3)2 4-N(CH3)2(217)
〃 〃
H 4-
N(C2H5)2 (218) 〃
〃 〃
3-N(C2H5)2 (21
9) 〃 〃
〃 2
-N(C2H5)2 (220) 〃
〃 4-O
CH3 4-OCH3 (221)
〃 〃
H 4-
OCH3 (222) 〃
〃 〃
2-CH3(223)
〃 〃
〃 3-CH3(2
24) 〃 〃
〃
4-CH3(225) 〃
〃 〃
H (226)
〃 〃
〃 4-Cl (2
27) 2-OCH3 6-
CH3 4-N(C2H5)2
4-N(C2H5)2 (228)
〃 〃
4-N(CH3)2 4-N(CH3)
2 (229) 〃
〃H
4-N(C2H5)2 (230)
〃 〃
〃 3-N(C2H5
)2 (231) 〃
〃 〃
2-N(C2H5)2 (232)
〃 〃
4-OCH3 4-OCH3
(233) 〃
〃H
4-OCH3 (234) 〃
〃
〃 2-CH3 (235)
〃 〃
〃 3
-CH3(236) 〃
〃 〃
H (237) 〃
〃
〃 4-Cl (238)
4-OCH3 2-CH3
4-N(C2H5)2
4-N(C2H5)2 (239)
〃 4-
N(CH3)2 4-N(CH3)2(2
40) 〃 〃
H
4-N(C2H5)2 (241)
〃
〃 3-N(C2H5)2
(242) 〃
〃 〃
2-N(C2H5)2 (243)
〃 〃
4-OCH3 4-OCH3 (2
44) 〃 〃
H
4-OCH3 (245) 〃
〃 〃
2-CH3 (246)
〃 〃
〃 3-CH
3 (247) 〃
〃 〃
H (248) 〃
〃 〃
4-Cl (249)
5-OCH3 2-CH3
4-N(C2H5)2 4-N
(C2H5)2 (250) 〃
〃 4-N(C
H3)2 4-N(CH3)2(251)
〃 〃
H 4-
N(C2H5)2 (252) 〃
〃 〃
3-N(C2H5)2 (25
3) 〃 〃
〃 2
-N(C2H5)2 (254) 〃
〃 4-O
CH3 4-OCH3 (255)
〃 〃
H 4-
OCH3 (256) 〃
〃 〃
2-CH3 (257)
〃 〃
〃 3-CH3(2
58) 〃 〃
〃
H (259) 〃
〃 〃
4-Cl (260) 3-
OCH3H (n=0)
4-N(C2H5)2 4-N(C2
H5) 2 (261) 〃
〃 4-N(CH3)
2 4-N(CH3)2(262)
〃 〃
〃 3-N(C2
H5) 2 (263) 〃
〃 〃
2-N(C2H5)2 (264)
〃 〃
4-OCH3 4-OC
H3 (265) 〃
〃H
4-OCH3 (266)
〃 〃
〃 2-CH3(26
7) 〃 〃
〃
3-CH3(268) 〃
〃 〃
4-CH3 (269)
〃 〃
〃 4-Cl (
270) 2-OCH3
〃 4-N(C2H5)2
4-N(C2H5)2 (271)
〃 〃
4-N(CH3)2 4-N(CH3)
2 (272) 〃
〃 〃
3-N(C2H5)2 (273)
〃 〃
〃 2-N(C2H5)
2 (274) 〃
〃 4-OCH3
4-OCH3 (275) 〃
〃
H4-OCH3 (27
6) 〃 〃
〃
2-CH3 (277) 〃
〃 〃
3-CH3 (278)
〃 〃
〃 4-CH3(
279) 〃 〃
〃
4-Cl 39] [Formula 40] [Formula 40] [Formula 41] [Formula 42] [Formula 42] [Formula 43] [Formula 44] [Formula 44] [Formula 46] ] [Chemical 47] [Chemical 47] [Chemical 47] [Chemical 49] [Chemical 53] [Image Omitted] [Image Omitted] [Image Omitted] [Image Omitted]

[Brief explanation of the drawing]

FIG. 1 is an IR spectrum diagram of an example of a carrier transport material according to the present invention.

FIG. 2 is an IR spectrum diagram of an example of a carrier transport material according to the present invention.

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

FIG. 4 is a sectional view of another example of an electrophotographic photoreceptor according to the present invention.

FIG. 5 is a sectional view of another example of an electrophotographic photoreceptor according to the present invention.

FIG. 6 is a sectional view of another example of an electrophotographic photoreceptor according to the present invention.

FIG. 7 is a sectional view of another example of an electrophotographic photoreceptor according to the present invention.

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

[Explanation of symbols]

1 Support 2 Carrier generation layer 3 Carrier transport layer 5 Intermediate layer 6 Layer containing a carrier generation substance and a carrier transport substance

Claims (4)

[Claims] [Claim 1] A bisstyryl compound represented by the following general formula [I]. embedded image [However, n=0 or n>1. When n=0, R1
is a chlorine atom or cyano group substituted at the 2- or 3-position with respect to the substituted amino group, or 2- to 4
- is a fluorine atom, bromine atom, iodine atom, or halogenated alkyl group substituted at the - position, and when n>1, R1 is a halogen atom substituted at the 2- to 4-position with respect to the substituted amino group. , a cyano group or a halogenated alkyl group having 1 to 4 carbon atoms. R2 may be different from each other and are substituents 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. Ar1
, Ar2 may be different from each other and are aryl groups represented by the following formula. {However, x≧0, y≧0
, z≧0, and when x, y, and z are 2 or more, the plurality of R3, R4, and R5 may be different from each other,
Hydrogen atom, halogen atom, cyano group, hydroxyl group, phenyl group, aralkyl group, alkyl group having 1 to 4 carbon atoms, halogenated alkyl group having 1 to 4 carbon atoms, [Formula 3] (However, R6 and R7 may be different from each other and are an alkyl group or an aralkyl group having 1 to 4 carbon atoms) and -OR8 (wherein R8 is an alkyl group having 1 to 4 carbon atoms)
is an alkyl group. ) is a substituent selected from }
] [Claim 2] A bisstyryl compound represented by the following general formula [II]. embedded image [However, n=0 or n>1. When n=0, R1
1 is a methoxy group or diethylamino group substituted at the 2- or 3-position with respect to the substituted amino group, or 2
an ethoxy group or dimethylamino group substituted at the - to 4- positions, and when n>1, R11 is a methoxy group or an ethoxy group substituted at the 2- to 4- positions with respect to the substituted amino group; It is a dimethylamino group or a diethylamino group. R12 may be different from each other,
The substituent is 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. Ar3,
Ar4 may be different from each other and is an aryl group represented by the following formula. {However, x≧0, y≧0
, z≧0, and when x, y, and z are 2 or more, the plurality of R13, R14, and R15 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. group, an alkyl group having 1 to 4 carbon atoms, [Formula 6] (However, R16 and R17 may be different from each other and are an alkyl group or an aralkyl group having 1 to 4 carbon atoms.), -OR18 (However, R18 has 1 to 4 carbon atoms.
is an alkyl group. ), -R19COOR20 (however, R19 is an alkylene group having 1 to 4 carbon atoms, and R
20 is an alkyl group. ) and -R19OCOR20
A substituent selected from }However, the following compounds are excluded. [Chemical formula 7] (Here, the plurality of R21 and R22 may be different from each other and are an alkyl group having 1 to 4 carbon atoms. Also, r≧2, t≧0.) 3. An electrophotographic photoreceptor containing a bisstyryl compound represented by the general formula [I] according to claim 1. 4. An electrophotographic photoreceptor containing a bisstyryl compound represented by the general formula [II] according to claim 2.