Electrophotographic photoconductor containing disazo and trisazo pigments

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an electrophotographic photoconductor and, more particularly to a single-layered organic electrophotographic photoconductor for use in electrophotographic copying machines and printers.
2. Discussion of Background
Inorganic photoconductive materials such as selenium, zinc oxide and cadmium sulfide; organic photoconductive materials such as azo pigments; and amorphous silicon, are conventionally known as photoconductive materials for use in electrophotographic photoconductors. However, the inorganic photoconductive materials have the drawbacks in photosensitivity, thermal stability, durability, impact resistance, and toxicity. For instance, selenium easily tends to crystallize, for example, when inappropriately heated, so that the characteristics readily deteriorate. A photoconductor employing cadmium sulfide or zinc oxide as a photoconductive material has humidity resistance and durability. The organic photoconductive materials can easily be made into a film with much more design freedom than the inorganic photoconductive materials because of the superior film-forming properties of the organic photoconductive materials.
In addition, the organic photoconductive materials are cheaper and cause no environmental pollution problems, so that electrophotographic photoconductors using the organic photoconductive materials have been actively developed in recent years.
Photoconductors comprising such organic photoconductive materials may be classified into two types, that is, a function-separated type photoconductor comprising a charge generation layer and a charge transport layer which are laminated, and a single-layered photoconductor comprising a photoconductive layer in which a charge generating material is dispersed in a binder resin.
In particular, many function-separated type photoconductors are put to practical use because of their superiority in photosensitivity.
For example, a function-separated laminated photoconductor comprising Chloro Diane Blue and a hydrazone compound in combination is proposed in Japanese Patent Publication 55-42380. Charge generating materials for use in such a function-separated laminated photoconductor are disclosed in Japanese Laid-Open Patent Applications 53-133445, 54-21728 and 54-22834; and charge transporting materials are disclosed in Japanese Laid-Open Patent Applications 58-198043 and 58-199352.
When preparing a laminated photoconductor, however, it is necessary to severely control the thickness of a charge generation layer within a range of 0.1 to 1.0 .mu.m for obtaining high photosensitivity. Such thickness control of the charge generation layer is susceptible to the surface conditions of an electroconductive support on which the charge generation layer is provided, and to the ambient conditions while a charge generation coating liquid is applied onto the support. Furthermore, for the preparation of such a laminated photoconductor comprising the charge generation layer and the charge transport layer, at least two coating steps are required. These factors largely affect the yield and manufacturing cost of the photoconductor.
For obtaining a laminated photoconductor with high photosensitivity, a charge transporting material with high electric charge mobility is demanded for use in the charge transport layer. Charge transporting materials with high electric charge mobility are almost limited to compounds which exhibit positive hole transporting characteristics. Therefore, photoconductors for use in practice are necessarily limited to photoconductors of a negative charging type, which are referred to as negatively-chargeable photoconductors.
Most of negatively-chargeable photoconductors are charged by use of corona charge with a negative polarity, so that a large amount of ozone is generated. The thus generated ozone is harmful to the human body, and impairs the photoconductor itself by the reaction with ozone, thereby shortening the life thereof. To prevent the generation of ozone, there are proposed a charging system capable of hindering the generation of ozone, a special system for decomposing the ozone discharged from a charging unit, and a special ozone exhaust system for removing ozone built up in an electrophotographic copying machine. Although some of these systems have been put to practical use, such systems have the shortcomings that they will make electrophotographic process complicated.
On the other hand, the single-layered electrophotographic photoconductors are generally known as positively-chargeable photoconductors. For example, there are proposed a photoconductor comprising polyvinyl carbazole and 2,4,7-trinitro-9-fluorenone in Japanese Patent Publication 50-10496; a photoconductor comprising a polyvinyl carbazole which is sensitized with a pyrylium salt-based pigment in Japanese Patent Publication 48-25658; a photoconductor comprising as a main component a eutectic complex; a photoconductor comprising a charge generating material and a charge transporting material in Japanese Laid-Open Patent Application 47-30330; photoconductors comprising a perylene pigment and a charge transporting material in Japanese Laid-Open Patent Applications 63-271461, 1-118143 and 3-65961; and a photoconductor comprising a phthalocyanine compound and a binder resin in Japanese Laid-Open Patent Application 3-65961.
However, the above-mentioned conventional single-layered photoconductors are still inferior in photosensitivity to the laminated photoconductors and the photosensitivity thereof is insufficient for use in practice.
In line with the recent trend of function-composition and improvement of copying machine, photoconductors capable of coping with a copying machine provided with both analog and digital functions have been developed. More specifically, to cope with the digital function of copying machine, it is desired that the photoconductor be highly photosensitive in a region with a wavelength of light from LD laser power source, namely, in the near infrared region; and to cope with the analog function of copying machine, it is required that the photoconductor be highly photosensitive in a region with the wavelength of white light, namely, in the visible region.
Function-separated laminated photoconductors which have a broad spectral sensitivity ranging from the visible region through the near infrared region are disclosed in Japanese Laid-Open Patent Applications 63-236047, 63-243950, 63-243951 and 1-315752, each of which comprises a mixture of a pigment having photosensitivity in the visible region and a pigment having photosensitivity in the near infrared region.
However, the charge transport layer is generally provided on the charge generation layer comprising the above-mentioned pigments and the charge transporting material contained in the charge transport layer absorbs light, so that the photosensitivity to light with a short wavelength of the function-separated laminated photoconductor is low. Thus, the spectral sensitivities of the conventional laminated photoconductors from the visible region to the near infrared region are not always sufficient for use in practice.
In addition, the laminated photoconductor has the optical problem of generation of interference light because of the presence of an interface between the charge generation layer and the charge transport layer.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide a single-layered electrophotographic photoconductor having high photosensitivities in a broad wave range including a visible region through a near infrared region, and having excellent performance stability and improved charging characteristics even when used repeatedly in electrophotographic image formation, which can be manufactured at a low cost.
The above object of the present invention can be attained by an electrophotographic photoconductor comprising an electroconductive support and a single-layered photoconductive layer formed thereon, comprising a charge transporting material, a binder resin, and a simultaneously pulverized mixture comprising at least one disazo pigment of formula (1) and at least one trisazo pigment of formula (2), which is obtained by simultaneously pulverizing the disazo pigment and the trisazo pigment: ##STR2## wherein R.sup.1 and R.sup.2 each is hydrogen, a halogen atom, trifluoromethyl group, nitro group or cyano group; R.sup.3 is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group; and Ar.sup.1, Ar.sup.2 and Ar.sup.3 each is a coupler radical, which may be the same or different, and is selected from the group consisting of coupler radicals of formulas (3) to (10): ##STR3## wherein X.sup.1 is --OH, --N(R.sup.4)(R.sup.5), or --NHSO.sub.2 R.sup.6, in which R.sup.4 and R.sup.5 each is hydrogen, an acyl group or an alkyl group which may have a substituent, and R.sup.6 is an aryl group which may have a substituent; Y.sup.1 is hydrogen, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group, a carboxyl group, a sulfone group, a benzimidazolyl group, a sulfamoyl group which may have a substituent, or --CON(R.sup.7)(Y.sup.2), in which R.sup.7 is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and Y.sup.2 is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or --N.dbd.C(R.sup.8)(R.sup.9), in which R.sup.8 is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or a styryl group which may have a substituent, R.sup.9 is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and R.sup.8 and R.sup.9 may form a ring in combination with a carbon atom to which R.sup.8 and R.sup.9 are bonded; and Z is a cyclic hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent; ##STR4## wherein n is an integer of 1 to 4; R.sup.10 is hydrogen, an alkyl group which may have a substituent, or an aryl group which may have a substituent; R.sup.11 is hydrogen, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an alkylsulfonyl group which may have a substituent, an alkylmercapto group which may have a substituent, a halogen atom, an aryl group which may have a substituent, an acyl group which may have a substituent, cyano group, nitro group, or an amino group which may have a substituent, and when n is 2, 3 or 4, R.sup.11 may be the same or different; and Y.sup.1 is the same as defined in formula (3); ##STR5## wherein R.sup.12 in formulas (5) and (6) is a hydrocarbon group which may have a substituent; ##STR6## wherein R.sup.13 in formulas (7) and (8) is an alkyl group, a carbamoyl group, a carboxyl group or an ester group thereof; and Ar.sup.4 is an aromatic hydrocarbon group which may have a substituent; ##STR7## wherein X.sup.2 in formulas (9) and (10) is a bivalent aromatic hydrocarbon group or a bivalent heterocyclic group.
In the first mentioned electrophotographic photoconductor, the charge transporting material may be an organic positive hole transporting material, or may comprise an organic positive hole transporting material and an organic acceptor compound.
When the electrophotographic photoconductor comprise an organic positive hole transporting material and an organic acceptor compound, the organic acceptor compound may have a reduction potential in a range of -0.2 to -1.2 v (vs SCE).
In the first mentioned electrophotographic photoconductor, the single-layered photoconductive layer may further comprise an antioxidant.

BRIEF DESCRIPTION OF THE DRAWINGS
A more complete appreciation of the invention and many of the attendant advantages thereof will be readily obtained as the same becomes better understood by reference to the following detailed description when considered in connection with the accompanying drawings, wherein:
FIG. 1 is a schematic cross-sectional view of a first embodiment of an electrophotographic photoconductor according to the present invention, which comprises an electroconductive layer and a photoconductive layer formed on the electroconductive layer;
FIG. 2 is a schematic cross-sectional view of a second embodiment of an electrophotographic photoconductor according to the present invention, in which an undercoat layer is provided between an electroconductive support and an photoconductive layer;
FIG. 3 is a schematic cross-sectional view of a third embodiment of an electrophotographic photoconductor according to the present invention, in which a protective layer is provided on a photoconductive layer;
FIG. 4 is a schematic cross-sectional view of a fourth embodiment of an electrophotographic photoconductor according to the present invention, in which an undercoat layer is provided between an electroconductive support and a photoconductive layer, and a protective layer is provided on the photoconductive layer;
FIG. 5 is a graph which shows the relationship between the oxidation potential of a charge transporting material to be employed and the charging potential of the obtained photoconductor; and
FIG. 6 is a graph which shows the spectral sensitivities of a comparative photoconductor and a photoconductor according to the present invention.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
In the electrophotographic photoconductor according to the present invention, a disazo pigment having the sensitivity to the visible region, and a trisazo pigment having the sensitivity to the light with a wavelength of 700 nm or more, namely, to the near infrared rays, are simultaneously mixed and pulverized, and the thus simultaneously pulverized mixture is contained in a single-layered photoconductive layer.
The thus formed photoconductor exhibits high photosensitivities in a broad region, from the visible region to the near infrared region.
The photosensitivities of the disazo pigment and the trisazo pigment can be remarkably increased by simultaneously pulverizing and mixing these pigments together with the application of some mechanical energy thereto, as compared with the case where the abovementioned two kinds of pigments are merely contained in the photoconductive layer. Such a sensitizing effect can be proved by examples to be described later.
The mixing ratio of the disazo pigment to the trisazo pigment for use in the present invention can be determined depending upon the kinds of disazo pigment and trisazo pigment employed, and upon the characteristics required for the obtained photoconductor, such as photosensitivity, charging characteristics, and resistance to gases.
Generally, however, it is preferable that the mixing ratio of the disazo pigment to the trisazo pigment in terms of (Disazo Pigment)/(Disazo Pigment+Trisazo Pigment) be in a range of 0.01 to 0.99, namely 0.01.ltoreq.(Disazo Pigment)/(Disazo Pigment+Trisazo Pigment).ltoreq.0.99.
A sufficiently high sensitizing effect can be obtained effectively when the above ratio is 0.01 or more, while the sensitizing effect and the resistance to gases can be improved when the ratio is 0.99 or less.
When uniform spectral photosensitivity in the visible region range through the near infrared region is taken into consideration, it is desirable that the above ratio be in the range of 0.1 to 0.9, namely, 0.1.ltoreq.(Disazo Pigment)/(Disazo Pigment+Trisazo Pigment).ltoreq.0.9.
To mix and pulverize the disazo pigment and the trisazo pigment, any pulverizing and mixing methods can be employed as long as mechanical energy, such as compression, shearing, grinding, friction, stretching, shock and vibration may be applied to the pigments. For example, a ball mill, a vibration mill, a disk-vibration mill, an attritor, a sand mill, a paint shaker, a jet mil, and an ultrasonic dispersion mixer are usable. It is recommendable that desired amounts of the disazo pigment and the trisazo pigment be placed in the same container, and simultaneously pulverized and dispersed with the application of the above-mentioned mechanical energy thereto in the presence of a dispersing solvent.
A mixture of the disazo pigment and the trisazo pigment is used as a charge generating material in the electrophotographic photoconductor of the present invention. In particular, a disazo pigment of formula (1), which can efficiently generate electric charges when exposed to light in the visible range of 400 to 700 nm, and a trisazo pigment of formula (2), which has high sensitivity to light with a wavelength of 700 nm or more are employed in the present invention: ##STR8## wherein Ar.sup.1, Ar.sup.2 and Ar.sup.3 each is a coupler radical, which may be the same or different; R.sup.1 and R.sup.2 each is hydrogen, a halogen, trifluoromethyl group, nitro group or cyano group; and R.sup.3 is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group.
The coupler radical represented by Ar.sup.1, Ar.sup.2 or Ar.sup.3 is selected from the group consisting of coupler radicals of formulas (3) to (10): ##STR9## wherein X.sup.1 is --OH, --N(R.sup.4)(R.sup.5), or --NHSO.sub.2 R.sup.6, in which R.sup.4 and R.sup.5 each is hydrogen, an acyl group or an alkyl group which may have a substituent, and R.sup.6 is an aryl group which may have a substituent; Y.sup.1 is hydrogen, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group, a carboxyl group, a sulfone group, a benzimidazolyl group, a sulfamoyl group which may have a substituent, or --CON(R.sup.7)(Y.sup.2), in which R.sup.7 is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and Y.sup.2 is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or --N.dbd.C(R.sup.8)(R.sup.9), in which R.sup.8 is a cyclic hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or a styryl group which may have a substituent, R.sup.9 is hydrogen, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, and R.sup.8 and R.sup.9 may form a ring in combination with a carbon atom to which R.sup.8 and R.sup.9 are bonded; and Z is a cyclic hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent; ##STR10## wherein n is an integer of 1 to 4; R.sup.10 is hydrogen, an alkyl group which may have a substituent, or an aryl group which may have a substituent; R.sup.11 is hydrogen, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an alkylsulfonyl group which may have a substituent, an alkylmercapto group which may have a substituent, a halogen atom, an aryl group which may have a substituent, an acyl group which may have a substituent, cyano group, nitro group, or an amino group which may have a substituent, and when n is 2, 3 or 4, R.sup.11 may be the same or different; and Y.sup.1 is the same as defined in formula (3); ##STR11## wherein R.sup.12 in formulas (5) and (6) is a hydrocarbon
group which may have a substituent; ##STR12## wherein R.sup.13 in formulas (7) and (8) is an alkyl group, a carbamoyl group, a carboxyl group or an ester group thereof; and Ar.sup.4 is an aromatic hydrocarbon group which may have a substituent; ##STR13## wherein X.sup.2 in formulas (9) and (10) is a bivalent aromatic hydrocarbon group or a bivalent heterocyclic group.
Specific examples of the coupler which can be represented by Ar.sup.1 --H, Ar.sup.2 --H or Ar.sup.3 --H for preparation of the disazo pigment of formula (1) and the trisazo pigment of formula (2) are as shown in Table 1 to Table 16.
TABLE 1______________________________________ ##STR14##Coupler Melting PointNo. R.sup.1 (R.sup.2).sub.n (.degree.C.)______________________________________ 1 H H 243-244 2 H 2-NO.sub.2 194-196 3 H 3-NO.sub.2 246-247 4 H 4-NO.sub.2 266-267.5 5 H 2-CF.sub.3 178-179 6 H 3-CF.sub.3 237.5-238.5 7 H 4-CF.sub.3 279-281 8 H 2-CN 221-222.5 9 H 3-CN 256.5-258.510 H 4-CN 274.5-27711 H 2-l 199-199.512 H 3-l 258.5-259.513 H 4-l 261.5-26214 H 2-Br 217-21815 H 3-Br 254-25516 H 4-Br 265-26817 H 2-Cl 228-23018 H 3-Cl 256.5-25719 H 4-Cl 264-26620 H 2-F 223.0-224.021 H 3-F 250.0-251.022 H 4-F 265.0-267.023 H 2-CH.sub.3 195.5-198.024 H 3-CH.sub.3 214.5-216.525 H 4-CH.sub.3 227.0-229.026 H 2-C.sub.2 H.sub.5 168.5-169.527 H 4-C.sub.2 H.sub.5 203.0-204.528 H 2-OCH.sub.3 167-16829 H 3-OCH.sub.3 195.5-198.030 H 4-OCH.sub.3 229-23031 H 2-OC.sub.2 H.sub.5 157-15832 H 3-OC.sub.2 H.sub.5 188.5-189.033 H 4-OC.sub.2 H.sub.5 225.0-225.534 H 4-N(CH.sub.3).sub.2 232.0-233.535 CH.sub.3 H 189.5-190.536 ##STR15## H 182.0-183.037 H 2-OCH.sub.3, 5-OCH.sub.3 186.0-188.038 H 2-OC.sub.2 H.sub.5, 5-OC.sub.2 H.sub.5 173.0-173.539 H 2-CH.sub.3, 5-CH.sub.3 207.0-208.540 H 2-Cl, 5-Cl 253.5-254.541 H 2-CH.sub.3, 5-Cl 245-24742 H 2-OCH.sub.3, 4-OCH.sub.3 151.0-152.043 H 2-CH.sub.3, 4-CH.sub.3 226-22844 H 2-CH.sub.3, 4-Cl 244-24545 H 2-NO.sub.2, 4-OCH.sub.3 179.5-181.046 H 3-OCH.sub.3, 5-OCH.sub.3 180.5-182.047 H 2-OCH.sub.3, 5-Cl 219.0-220.048 H 2-OCH.sub.3, 5-OCH.sub.3, 193.5-195.5 4-Cl49 H 2-OCH.sub.3, 4-OCH.sub.3, 193-194 5-Cl50 H 3-Cl, 4-Cl 272.5-273.551 H 2-Cl, 4-Cl, 5-Cl 257.5-258.552 H 2-CH.sub.3, 3-Cl 227.5-228.553 H 3-Cl, 4-CH.sub.3 259.5-260.554 H 2-F, 4-F 246.0-246.555 H 2-F, 5-F 259.0-260.056 H 2-Cl, 4-NO.sub.2 283.0-284.057 H 2-NO.sub.2, 4-Cl 216.5-227.558 H 2-Cl, 3-Cl, 280.0-281.5 4-Cl, 5-Cl59 H 4-OH 268______________________________________
TABLE 2______________________________________ ##STR16##Coupler Melting PointNo. R.sup.1 (R.sup.2).sub.n (.degree.C.)______________________________________60 H H >30061 H 2-NO.sub.2 283-28462 H 3-NO.sub.2 >30063 H 4-NO.sub.2 >30064 H 2-Cl >30065 H 3-Cl >30066 H 4-Cl >30067 H 2-CH.sub.3 >30068 H 3-CH.sub.3 >30069 H 4-CH.sub.3 >30070 H 2-C.sub.2 H.sub.5 271-27371 H 4-C.sub.2 H.sub.5 >30072 H 2-OCH.sub.3 276-27873 H 3-OCH.sub.3 >30074 H 4-OCH.sub.3 >30075 H 2-OC.sub.2 H.sub.5 273.5-275.076 H 4-OC.sub.2 H.sub.5 >30077 H 2-CH.sub.2, 4-OCH.sub.3 29678 H 2-CH.sub.3, 4-CH.sub.3 >30079 H 2-CH.sub.3, 5-CH.sub.3 274.0-276.080 H 2-CH.sub.3, 6-CH.sub.3 >30081 H 2-OCH.sub.3, 4-OCH.sub.3 296.5-298.582 H 2-OCH.sub.3, 5-OCH.sub.3 284.5-286.583 H 3-OCH.sub.2, 5-OCH.sub.3 300.5-302.084 H 2-CH.sub.3, 3-Cl 296.0-297.585 H 2-CH.sub.3, 4-Cl >30086 H 2-CH.sub.3, 5-Cl 290.5-292.087 H ##STR17## 30488 H 2-CH(CH.sub.3).sub.2 239.0-240.0______________________________________
TABLE 3__________________________________________________________________________ ##STR18##Coupler Melting PointNo. R.sup.1 (R.sup.2).sub.n (.degree.C.)__________________________________________________________________________ 89 H H 228.0-230.0 90 H 4-N(CH.sub.3).sub.2 238.5-240.0 91 H 2-OCH.sub.3 218.0-222.0 92 H 3-OCH.sub.3 186.5-188.5 93 H 4-OCH.sub.3 224.5-225.0 94 H 4-OC.sub.2 H.sub.5 236.0-237.5 95 H 2-CH.sub.3 227.0-228.0 96 H 3-CH.sub.3 212.5-214.0 97 H 4-CH.sub.3 233.0-236.0 98 H 2-F 233.0-233.5 99 H 3-F 248.5100 H 4-F 239.5-240.0101 H 2-Cl 254.0-255.0102 H 3-Cl 226.5-230.0103 H 4-Cl 265.5-269.0104 H 2-Br 243.0105 H 3-Br 231.0-231.5106 H 4-Br 259.0107 H 2-Cl, 4-Cl 251.5-252.0108 H 3-Cl, 4-Cl 260.0-261.0109 H 2-CN 175.0-176.5110 H 4-CN 267.5-268.0111 H 2-NO.sub.2 240.0112 H 3-NO.sub.2 255.5-257.0113 H 4-NO.sub.2 260.0-261.0114 H 2-CH.sub.3, 4-CH.sub.3 234.5-236.5115 H 2-OCH.sub.3, 5-OCH.sub.3 221.5-222.0116 H 2-OCH.sub.3, 3-OCH.sub.3 191.0-192.0 4-OCH.sub.3117 CH.sub.3 H 248.5-250.0118 ##STR19## H 182.5-185.0119 ##STR20## H 213.0-214.5120 H ##STR21## 237.0-237.5__________________________________________________________________________
TABLE 4______________________________________ ##STR22##Coupler MeltingNo. R.sup.1 R.sup.2 Point (.degree.C.)______________________________________121 CH.sub.3 CH.sub.3 232.5-233.0122 H ##STR23## 208.5-209.0123 H ##STR24## 224.0-224.5124 H ##STR25## 197.5-199.0125 H ##STR26## 188.0-188.5126 H ##STR27## 227.0-228.0127 CH.sub.3 ##STR28## 225.5-226.0128 H ##STR29## 212.5-214.0129 H ##STR30## 257130 H ##STR31## 250131 H ##STR32## 232.5-236.0132 H ##STR33## 240.5-241.5______________________________________
TABLE 5______________________________________ ##STR34##Coupler No. (R).sub.n Melting Point (.degree.C.)______________________________________133 H >300134 2-OCH.sub.3 268135 3-OCH.sub.3 281.0-283.0136 4-OCH.sub.3 293137 2-CH.sub.3 297138 3-CH.sub.3 296139 4-CH.sub.3 >300140 4-Cl >300141 2-NO.sub.2 >300142 4-NO.sub.2 >300143 2-OH >300144 2-OH, 3-NO.sub.2 >300145 2-OH, 5-NO.sub.2 >300146 2-OH, 3-OCH.sub.3 >300______________________________________
TABLE 6______________________________________ ##STR35##Coupler No. (R).sub.n Melting Point (.degree.C.)______________________________________147 4-Cl >300148 2-NO.sub.2 268-274149 3-NO.sub.2 >300150 4-NO.sub.2 >300151 ##STR36## 296152 H 300-307153 2-OCH.sub.3 242-248154 3-OCH.sub.3 269-275155 4-OCH.sub.3 312156 2-CH.sub.3 265-270157 3-CH.sub.3 270-278158 4-CH.sub.3 304159 2-Cl 283-288160 3-Cl 281-287______________________________________
TABLE 7______________________________________ ##STR37##Coupler No. R.sup.1 (R.sup.2).sub.n Melting Point (.degree.C.)______________________________________161 H 2-OCH.sub.3, 4-Cl, 208.0-208.5 5-CH.sub.3162 OCH.sub.3 H 230.5-231.5163 OCH.sub.3 2-CH.sub.3 205.5-206.0164 OCH.sub.3 2-OCH.sub.3, 5-OCH.sub.3 245.5-246.0 4-Cl______________________________________
TABLE 8______________________________________ ##STR38##Coupler No. X Melting Point (.degree.C.)______________________________________165 ##STR39## 207.0-209.0166 ##STR40## 257.0-259.0167 ##STR41## 290______________________________________
TABLE 9______________________________________ ##STR42##CouplerNo. R.sup.1 Melting Point (.degree.C.)______________________________________168 ##STR43## >300169 ##STR44## >300170 ##STR45## >300171 ##STR46## 298______________________________________
TABLE 10__________________________________________________________________________ ##STR47##CouplerNo. X R Melting Point (.degree.C.)__________________________________________________________________________172 ##STR48## ##STR49## 180-183173 ##STR50## ##STR51## 228.5-229.5174 ##STR52## ##STR53## >262175 ##STR54## ##STR55## 226.5-227.0176 ##STR56## ##STR57## 308-310177 ##STR58## ##STR59## 222-223__________________________________________________________________________
TABLE 11__________________________________________________________________________ ##STR60##Coupler No. R.sup.1 R.sup.2 Melting Point (.degree.C.)__________________________________________________________________________178 H H 220.5-221.5179 CH.sub.3 H 190.5-192.5180 CH.sub.3 CH.sub.3 196.0-198.0181 H ##STR61## 222.0-223.0__________________________________________________________________________
TABLE 12__________________________________________________________________________Coupler Melting PointNo. Formula (.degree.C.)__________________________________________________________________________182 ##STR62## >300183 ##STR63## >300184 ##STR64## >300185 ##STR65## >300186 ##STR66## >300187 ##STR67## >300188 ##STR68## 122.0-122.5189 ##STR69## 222.5-224.0190 ##STR70## 74.5-75.5191 ##STR71## 275.5-276.5192 ##STR72## 130.5-131.5193 ##STR73## >300194 ##STR74## >300195 ##STR75## >300196 ##STR76## 172.5-173.5197 ##STR77## 262.5-265.5198 ##STR78## >300199 ##STR79## >300200 ##STR80## 128.0-129.0__________________________________________________________________________
TABLE 13______________________________________ ##STR81##Coupler No. R.sup.1 (R.sup.2).sub.n Melting Point (.degree.C.)______________________________________201 Cl H >300202 Cl 2-OCH.sub.3 >300203 Cl 3-OCH.sub.3 >300204 Cl 4-OCH.sub.3 >300205 Cl 2-CH.sub.3 >300206 Cl 3-CH.sub.3 >300207 Cl 4-CH.sub.3 >300208 Cl 2-Cl >300209 Cl 3-Cl >300210 Cl 4-Cl >300211 Cl 2-NO.sub.2 >300212 Cl 3-NO.sub.2 >300213 Cl 4-NO.sub.2 >300214 Cl 2-CH.sub.3, 4-Cl >300215 Cl 2-CH.sub.3, 4-CH.sub.3 >300216 Cl 2-C.sub.2 H.sub.5 299.0-301.0217 CH.sub.3 H >300218 CH.sub.3 2-OCH.sub.3 297219 CH.sub.3 3-OCH.sub.3 >300220 CH.sub.3 4-OCH.sub.3 >300221 CH.sub.3 2-CH.sub.3 >300222 CH.sub.3 3-CH.sub.3 >300223 CH.sub.3 4-CH.sub.3 >300224 CH.sub.3 2-Cl >300225 CH.sub.3 3-Cl >300226 CH.sub.3 4-Cl >300227 CH.sub.3 2-NO.sub.2 >300228 CH.sub.3 3-NO.sub.2 >300229 CH.sub.3 4-NO.sub.2 >300230 CH.sub.3 2-CH.sub.3, 4-Cl >300231 CH.sub.3 2-CH.sub.3, 4-CH.sub.3 >300232 CH.sub.3 2-C.sub.2 H.sub.5 268.5-270.0233 OCH.sub.3 H 289.0234 OCH.sub.3 2-OCH.sub.3 268.0-270.0235 OCH.sub.3 3-OCH.sub.3 >300236 OCH.sub.3 4-OCH.sub.3 >300237 OCH.sub.3 2-CH.sub.3 284.5-285.5238 OCH.sub.3 3-CH.sub.3 >300239 OCH.sub.3 4-CH.sub.3 >300240 OCH.sub.3 3-Cl >300242 OCH.sub.3 4-Cl >300243 OCH.sub.3 2-NO.sub.2 >300244 OCH.sub.3 3-NO.sub.2 >300245 OCH.sub.3 4-NO.sub.2 >300246 OCH.sub.3 2-C.sub.2 H.sub.5 264.5-266.5______________________________________
TABLE 14______________________________________Coupler No. Formula______________________________________247 ##STR82##248 ##STR83##249 ##STR84##250 ##STR85##251 ##STR86##252 ##STR87##253 ##STR88##254 ##STR89##255 ##STR90##256 ##STR91##257 ##STR92##258 ##STR93##______________________________________
TABLE 15______________________________________ ##STR94##Coupler No. (R.sup.2).sub.n______________________________________259 2-Cl, 3-Cl260 2-Cl, 4-Cl261 3-Cl, 5-Cl______________________________________
TABLE 16______________________________________ ##STR95##Coupler No. (R.sup.2).sub.n______________________________________262 4-CH.sub.2263 3-NO.sub.2264 2-Cl265 3-Cl266 4-Cl267 2-Cl, 3-Cl268 2-Cl, 4-Cl,269 3-Cl, 5-Cl270 2-Cl, 5-Cl271 3-Cl, 4-Cl______________________________________
In the electrophotographic photoconductor of the present invention, disazo pigments of formula (11) and formula (12) are particularly preferable because of their high sensitivities in the visible light range: ##STR96##
When any of these disazo pigments of formulas (11) and (12) and the trisazo pigment of the previously mentioned formula (2) are mixed and pulverized simultaneously, a pigment dispersion coating liquid with excellent stability can be obtained. Therefore, a photoconductive layer with an increased sensitizing effect can be formed by coating the above pigment dispersion coating liquid.
As the trisazo pigment of formula (2), the following compound of formula (13) is preferably employed in the present invention: ##STR97## wherein R.sup.31 to R.sup.39 each is hydrogen, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, chlorine, fluorine, iodine, bromine, CH.sub.3 --, C.sub.2 H.sub.5 O--, C.sub.3 H.sub.7 O--, --NO.sub.2, --CN, --CF.sub.3 or --OH.
The trisazo compound of formula (13) can generate electric charges very efficiently, particularly by the application of light with a wavelength of 700 nm or more in the near infrared region. When the trisazo compound of formula (13) is simultaneously pulverized with the above-mentioned disazo pigments of formulas (11) or (12) and the thus obtained mixture is contained in a single-layered photoconductive layer, the photosensitivity of the obtained photoconductor becomes sufficiently high in a broad range from the visible light range to the near infrared range.
In particular, to prepare a photoconductor with a high sensitivity to the LD light of 780 to 850 nm, the following trisazo pigments of formulas (13-a) and (13-b) are advantageous because they have high sensitivities in a board wave range up to 850 nm: ##STR98##
In the electrophotographic photoconductor of the present invention, oxazole derivatives, imidazole derivatives and triphenylamine derivatives can be used as charge transporting materials.
Further, it is preferable that the charge transporting material for use in the present invention be a positive hole transporting material which is selected from the group consisting of the following compounds of formulas (14) to (32): ##STR99## wherein R.sup.1 is methyl group, ethyl group, 2-hydroxyethyl group or 2-chloroethyl group; R.sup.2 is methyl group, ethyl group, benzyl group or phenyl group; and R.sup.3 is hydrogen, chlorine, bromine, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a dialkylamino group, or nitro group; ##STR100## wherein Ar is naphthalene ring, anthracene ring, styryl ring, each of which may have a substituent, pyridyl ring, furan ring, or thiophene ring; and R is an alkyl group or benzyl group; ##STR101## wherein R.sup.1 is an alkyl group, benzyl group, phenyl group, or naphthyl group; R.sup.2 is hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a dialkylamino group, a diaralkylamino group or a diarylamino group; n is an integer of 1 to 4; when n is 2 or more, R.sup.2 may be the same or different; and R.sup.3 is hydrogen or methoxy group; ##STR102## wherein R.sup.1 is an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic ring; R.sup.2 and R.sup.3 may be the same or different and each is hydrogen, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R.sup.2 and R.sup.3 may form a nitrogen-containing heterocyclic ring in combination; and R.sup.4 is hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group, or a halogen atom, and may be the same or different; ##STR103## wherein R.sup.1 is hydrogen, a substituted or unsubstituted alkyl group, or phenyl group; R.sup.2 is hydrogen, a substituted or unsubstituted alkyl group, an alkoxyl group or a halogen atom; ##STR104## wherein R is hydrogen or a halogen atom; Ar is phenyl group, naphthyl group, anthryl group or carbazolyl group, each of which may have a substituent; ##STR105## wherein R.sup.1 is hydrogen, a halogen atom, cyano group, an alkoxyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; and Ar is ##STR106## wherein R.sup.2 is an alkyl group having 1 to 4 carbon atoms; R.sup.3 is hydrogen, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a dialkylamino group; n is an integer of 1 or 2; when n is 2, R.sup.3 may be the same or different; and R.sup.4 and R.sup.5 each is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted benzyl group; ##STR107## wherein R is carbazolyl group, pyridyl group, thienyl group, indolyl group, furyl group, a substituted or unsubstituted phenyl group, styryl group, naphthyl group, or anthryl group, each of which may have a substituent selected from the group consisting of a dialkylamino group, an alkyl group, an alkoxyl group, carboxyl group or an ester group thereof, a halogen atom, cyano group, an aralkylamino group, an N-alkyl-N-aralkylamino group, amino group, nitro group and acetylamino group; ##STR108## wherein R.sup.1 is a lower alkyl group, a substituted or unsubstituted phenyl group, or benzyl group; R.sup.2 and R.sup.3 each is hydrogen, a lower alkyl group, a lower alkoxyl group, a halogen atom, nitro group, or an amino group which may have as a substituent a lower alkyl group or benzyl group; and n is an integer of 1 or 2; ##STR109## wherein R.sup.1 is hydrogen, an alkyl group, an alkoxyl group or a halogen atom; R.sup.2 and R.sup.3 each is an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; R.sup.4 is hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group; and Ar is a substituted or unsubstituted phenyl group or naphthyl group; ##STR110## wherein n is an integer of 0 or 1; R.sup.1 is hydrogen, an alkyl group or a substituted or unsubstituted phenyl group; Ar.sup.1 is a substituted or unsubstituted aryl group; R.sup.5 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is ##STR111## 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, in which R.sup.2 is hydrogen, an alkyl group, an alkoxyl group, a halogen atom, or ##STR112## in which R.sup.3 and R.sup.4 each is an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R.sup.3 and R.sup.4 may be the same or different and may form a ring in combination; m is an integer of 0 to 3; and when m is 2 or more, R.sup.2 may be the same or different; and when n is 0, A and R.sup.1 may form a ring in combination; ##STR113## wherein R.sup.1, R.sup.2 and R.sup.3 each is hydrogen, a lower alkyl group, a lower alkoxyl group, a dialkylamino group or a halogen atom; and n is an integer of 0 or 1; ##STR114## wherein R.sup.1 and R.sup.2 each is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is a substituted amino group, a substituted or unsubstituted aryl group, or an allyl group; ##STR115## wherein X is hydrogen, a lower alkyl group, or a halogen atom; R is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and A is a substituted amino group, or a substituted or unsubstituted aryl group; ##STR116## wherein R.sup.1 is a lower alkyl group, a lower alkoxyl group, or a halogen atom; n is an integer of 0 to 4; and R.sup.2 and R.sup.3 may be the same or different, and each is hydrogen, a lower alkyl group, a lower alkoxyl group, or a halogen atom; ##STR117## wherein R.sup.1, R.sup.3 and R.sup.4 each is hydrogen, an amino group, a thioalkoxyl group, an aryloxy group, methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group; R.sup.2 is hydrogen, an alkoxyl group, a substituted or unsubstituted alkyl group, or a halogen atom, provided that not all of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen at the same time; k, l, m and n each is an integer of 1 to 4, and when each of k, l, m and n is 2, 3 or 4, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may be the same or different; ##STR118## wherein Ar is a condensed polycyclic hydrocarbon group having 18 or less carbon atoms; R.sup.1 and R.sup.2 may be the same or different, and each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxyl group, or a substituted or unsubstituted phenyl group;
A--CH.dbd.CH--Ar--CH.dbd.CH--A (31)
wherein Ar is a substituted or unsubstituted aromatic hydrocarbon group; and A is ##STR119## in which Ar' is a substituted or unsubstituted aromatic hydrocarbon group; and R.sup.1 and R.sup.2 each is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and ##STR120## wherein Ar is an aromatic hydrocarbon group; R is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and n is an integer of 0 or 1, and m is an integer of 1 or 2, and when n=0 and m=1, Ar and R may form a ring in combination.
Specific examples of the compound of formula (14) are 9-ethylcarbazole-3-aldehyde-1-methyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1-benzyl-1-phenylhydrazone, and 9-ethylcarbazole-3-aldehyde-1,1-diphenylhydrazone.
Specific examples of the compound of formula (15) are 4-diethylaminostyryl-.beta.-aldehyde-1-methyl-1-phenylhydrazone, and 4-methyoxynaphthalene-1-aldehyde-1-benzyl-1-phenylhydrazone.
Specific examples of the compound of formula (16) are 4-methoxybenzaldehyde-1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde-1-benzyl-1-phenylhydrazone, 4-diethylaminobenzaldehyde-1,1-diphenylhydrazone, 4-methoxybenzaldehyde-1-benzyl-1-(4-methoxy)phenylhydrazone, 4-diphenylaminobenzaldehyde-1-benzyl-1-phenylhydrazone, and 4-dibenzylaminobenzaldehyde-1,1-diphenylhydrazone.
Specific examples of the compound of formula (17) are 1,1-bis(4-dibenzylaminophenyl)propane, tris(4-diethylaminophenyl)methane, 1,1-bis(4-dibenzylaminophenyl)propane, and 2,2'-dimethyl-4,4'-bis(diethylamino)triphenylmethane.
As the compound of formula (18), N-ethyl-3,6-tetrabenzylaminocarbazole can be employed.
Specific examples of the compound of formula (19) are 9-(4-diethylaminostyryl)anthracene, and 9-bromo-10-(4-diethylaminostyryl)anthracene.
Specific examples of the compound of formula (20) are 9-(4-dimethylaminobenzylidene)fluorene, and 3-(9-fluorenylidene)-9-ethylcarbazole.
Specific examples of the compound of formula (21) are 1,2-bis(4-diethylaminostyryl)benzene, and 1,2-bis(2,4-dimethoxystyryl)benzene.
Specific examples of the compound of formula (22) are 3-styryl-9-ethylcarbazole, and 3-(4-methoxystyryl)-9-ethylcarbazole.
Specific examples of the compound of formula (23) are 4-diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolyllaminostilbene, 1-(4-diphenylaminostyryl)naphthalene, and 1-(4-diethylaminostyryl)naphthalene.
Specific examples of the compound of formula (24) are 4'-diphenylamino-.alpha.-phenylstilbene, and 4'-bis(methylphenyl)amino-.alpha.-phenylstilbene.
Specific examples of the compound of formula (25) are 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline, and 1-phenyl-3-(4-dimethylaminostyryl)-5-(4-dimethylaminophenyl)pyrazoline.
Specific examples of the compound of formula (26) are 2,5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole, 2-N,N-diphenylamino-5-(4-diethylaminophenyl)-1,3,4-oxadiazole, and 2-(4-dimethylaminophenyl)-5-(4-diethylaminophenyl)-1,3,4-oxadiazole.
Specific examples of the compound of formula (27) are 2-N,N-diphenylamino-5-(N-ethylcarbazole-3-yl)-1,3,4-oxadiazole, and 2-(4-diethylaminophenyl)-5-(N-ethylcarbazole-3-yl)-1,3,4-oxadiazole.
Specific examples of the compound of formula (28) are N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-bisphenyl]-4,4'-diamine, and 3,3'-dimethyl-N,N,N',N'-tetrakis(4-methylphenyl)-[1,1'-biphenyl]-diamine.
Specific examples of the biphenylamine compound of formula (29) are 4'-methoxy-N,N-diphenyl-[1,1'-biphenyl]-4-amine, 4'-methyl-N,N'-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine, and 4'-methoxy-N,N'-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine.
Specific examples of the triarylamine compound of formula (30) are 1-phenylaminopyrene, and 1-di(p-tolylamino)pyrene.
Specific examples of the diolefin aromatic compound of formula (31) are 1,4-bis(4-diphenylaminostyryl)benzene, and 1,4-bis[4-di(p-tolyl)aminostyryl]benzene.
Specific examples of the styrylpyrene compound of formula (32) are 1-(4-diphenylaminostyryl)pyrene, and 1-[4-di(p-tolyl)aminostyryl]pyrene.
These charge transporting materials may be used alone or in combination.
It is preferable that the charge transporting material for use in the present invention have an oxidation potential of +0.5 V (vs SCE) or more. In particular, the charge transporting materials of formulas (14), (15), (17), (19), (22), (23), (24), (28), (29), (30) and (31) are preferable from the viewpoints of charging characteristics and photosensitivity of the obtained photoconductor. In particular, an electrophotographic photoconductor employing the positive hole transporting compound of formula (17) is superior to others in the charging stability when repeatedly used in electrophotographic process.
The oxidation potential of the charge transporting material for use in the present invention means a half-wave potential obtained by conventionally known cyclic voltametry, using acetonitrile as a solvent, 0.1 MTEAP as an electrolyte, and a saturated calomel electrode (SCE) as a reference electrode.
The charge transporting material for use in the electrophotographic photoconductor of the present invention may comprise the above-mentioned organic positive hole transporting material and an organic acceptor compound.
Any conventional organic acceptor compounds can be employed in the present invention. Particularly, it is preferable to use organic acceptor compounds of formulas (1) to (14) in combination:
[Organic Acceptor Compound of Formula (1)] ##STR121## wherein R.sup.1 is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group or nitro group; n is an integer of 1 to 3; X is ##STR122## in which R.sup.2 and R.sup.3 each is an alkyl group, and R.sup.3 may be bonded to each other.
[Organic Acceptor Compound of Formula (2)] ##STR123## wherein Ar is a substituted or unsubstituted aromatic group; and X is cyano group or an alkoxycarbonyl group.
[Organic Acceptor Compound of Formula (3)]
Ar--CH.dbd.C(COOR).sub.2 (3)
wherein Ar is a substituted or unsubstituted aromatic group; and R is an alkyl group, and R may be bonded to each other to form a ring.
[Organic Acceptor Compound of Formula (4)] ##STR124## wherein X is sulfur or selenium; Y is a substituted or unsubstituted alkyl group, an aryl group, or cyano group; R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, cyano group, nitro group, a halogen atom, or hydrogen; and n is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (5)]
Ar--CH.dbd.CHNO.sub.2 (5)
wherein Ar is a substituted or unsubstituted aromatic group.
[Organic Acceptor Compound of Formula (6)] ##STR125## wherein R.sup.1 and R.sup.2 each is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a heterocyclic aromatic group.
[Organic Acceptor Compound of Formula (7)] ##STR126## wherein R.sup.1 is hydrogen, a halogen atom, an alkyl group, or a substituted or unsubstituted phenyl group; R.sup.2 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a halogen atom, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group, or nitro group; and n is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (8)] ##STR127## wherein R.sup.3 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a halogen atom, an alkoxycarbonyl group, an N-alkylcarbamoyl group, cyano group, or nitro group; and n is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (9)] ##STR128## wherein R.sup.1 and R.sup.2 each is a substituted or unsubstituted phenyl group, a substituted or unsubstituted polycyclic aromatic group, or a substituted or unsubstituted heterocyclic group.
[Organic Acceptor Compound (10)] ##STR129## wherein R.sup.1 and R.sup.2 each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR130## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (11)] ##STR131## wherein R.sup.3 and R.sup.4 each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR132## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (12)] ##STR133## wherein R.sup.5 and R.sup.6 each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group an amino group, or a vinyl group of ##STR134## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (13)] ##STR135## wherein R.sup.7 and R.sup.8 each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, an N-alkylcarbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, cyano group, nitro group, an alkoxyl group, an aryloxy group, an amino group, or a vinyl group of ##STR136## in which X is hydrogen or an alkyl group, and at least one of Y or Z is a substituted or unsubstituted phenyl group and the other is hydrogen; and n and m each is an integer of 1 to 3.
[Organic Acceptor Compound of Formula (14)] ##STR137## wherein X is O or N--R, in which R is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.
TABLES 17-30 respectively show specific examples of the organic acceptor compound of formulae (1) to (14).
TABLE 17______________________________________ ##STR138## (1)Compound No. X R.sup.1______________________________________ 1 C(CN).sub.2 4'-NO.sub.2 2 C(CN).sub.2 3'-NO.sub.2 3 C(CN).sub.2 3'-NO.sub.2 -4'-Cl 4 C(CN).sub.2 4'-CN 5 C(CN).sub.2 4'-Cl 6 C(CN).sub.2 4'-COOC.sub.2 H.sub.5 7 C(CN).sub.2 4'-COOC.sub.4 H.sub.9 8 C(CN).sub.2 4'-CF.sub.3 9 C(CN).sub.2 4'-C.sub.4 H.sub.910 ##STR139## 4'-NO.sub.211 ##STR140## 3'-NO.sub.2 -4'-Cl12 ##STR141## 3'-NO.sub.2 -4'-CH.sub.313 ##STR142## 4'-CN14 ##STR143## 4'-Cl15 ##STR144## 4'-COOCH.sub.2 H.sub.516 ##STR145## 4'-CF.sub.317 ##STR146## 4'-C.sub.4 H.sub.918 ##STR147## 4'-NO.sub.219 ##STR148## 3'-NO.sub.220 ##STR149## 3'-NO.sub.2, 4'-Cl21 ##STR150## 3'-NO.sub.2, 4'-CH.sub.322 ##STR151## 4'-CN23 ##STR152## 3'-CF.sub.3, 4'-CN24 ##STR153## 4'-Cl25 ##STR154## 4'-COOC.sub.2 H.sub.526 ##STR155## 4'-COOC.sub.4 H.sub.927 ##STR156## 4'-CON(C.sub.4 H.sub.9).sub.228 ##STR157## 4'-CF.sub.329 ##STR158## 4'-C.sub.2 H.sub.530 ##STR159## 4'-C.sub.4 H.sub.931 C(COOCH.sub.3).sub.2 4'-NO.sub.232 C(COOCH.sub.3).sub.2 4'-Cl33 C(COOCH.sub.3).sub.2 4'-COOC.sub.4 H.sub.934 C(COOCH.sub.3).sub.2 4'-CF.sub.335 C(COOCH.sub.3).sub.2 4'-C.sub.4 H.sub.936 C(COOC.sub.4 H.sub.9).sub.2 4'-NO.sub.237 C(COOC.sub.4 H.sub.9).sub.2 2'-CH.sub.3, 4'-NO.sub.238 C(COOC.sub.4 H.sub.9).sub.2 3'-NO.sub.2, 4'-Cl39 C(COOC.sub.4 H.sub.9).sub.2 3'-NO.sub.2, 4'-CH.sub.340 C(COOC.sub.4 H.sub.9).sub.2 4'-CN41 C(COOC.sub.4 H.sub.9).sub.2 4'-Cl42 C(COOC.sub.4 H.sub.9).sub.2 4'-COOC.sub.4 H.sub.943 C(COOC.sub.4 H.sub.9).sub.2 4'-CF.sub.344 C(COOC.sub.4 H.sub.9).sub.2 4'-C.sub.4 H.sub.945 ##STR160## 4'-NO.sub.246 ##STR161## 2'-CH.sub.3 -4'-NO.sub.247 ##STR162## 4'-CN48 ##STR163## 4'-Cl49 ##STR164## 4'-COOC.sub.2 H.sub.550 ##STR165## 4'-COOC.sub.4 H.sub.951 ##STR166## 4'-CF.sub.352 ##STR167## 4'-C.sub.2 H.sub.553 ##STR168## 4'-C.sub.4 H.sub.9______________________________________
TABLE 18__________________________________________________________________________ ##STR169## (2)Compound No. X Ar__________________________________________________________________________ 1 CN ##STR170## 2 CN ##STR171## 3 CN ##STR172## 4 CN ##STR173## 5 CN ##STR174## 6 CN ##STR175## 7 CN ##STR176## 8 CN ##STR177## 9 CN ##STR178##10 CN ##STR179##11 CN ##STR180##12 CN ##STR181##13 CN ##STR182##14 CN ##STR183##15 CN ##STR184##16 CN ##STR185##17 CN ##STR186##18 CN ##STR187##19 CN ##STR188##20 CN ##STR189##21 CN ##STR190##22 CN ##STR191##23 CN ##STR192##24 CN ##STR193##25 CN ##STR194##26 CN ##STR195##27 CN ##STR196##28 CN ##STR197##29 CN ##STR198##30 CN ##STR199##31 CN ##STR200##32 CN ##STR201##33 CN ##STR202##34 CN ##STR203##35 CN ##STR204##36 CN ##STR205##37 COOC.sub.2 H.sub.5 ##STR206##38 COOC.sub.2 H.sub.5 ##STR207##39 COOC.sub.2 H.sub.5 ##STR208##40 COOC.sub.2 H.sub.5 ##STR209##41 COOC.sub.2 H.sub.5 ##STR210##42 COOC.sub.2 H.sub.5 ##STR211##43 COOC.sub.2 H.sub.5 ##STR212##44 COOC.sub.2 H.sub.5 ##STR213##45 COOC.sub.2 H.sub.5 ##STR214##46 COOC.sub.2 H.sub.5 ##STR215##47 COOC.sub.2 H.sub.5 ##STR216##48 COOC.sub.2 H.sub.5 ##STR217##49 COOC.sub.2 H.sub.5 ##STR218##50 COOC.sub.2 H.sub.5 ##STR219##51 COOC.sub.2 H.sub.5 ##STR220##52 COOC.sub.2 H.sub.5 ##STR221##53 COOC.sub.2 H.sub.5 ##STR222##54 COOC.sub.4 H.sub.9 ##STR223##55 COOC.sub.4 H.sub.9 ##STR224##56 COOC.sub.4 H.sub.9 ##STR225##57 COOC.sub.4 H.sub.9 ##STR226##58 COOC.sub.4 H.sub.9 ##STR227##59 COOC.sub.4 H.sub.9 ##STR228##60 COOC.sub.4 H.sub.9 ##STR229##61 COOC.sub.4 H.sub.9 ##STR230##62 COOC.sub.4 H.sub.9 ##STR231##63 COOC.sub.4 H.sub.9 ##STR232##64 COOC.sub.4 H.sub.9 ##STR233##65 COOC.sub.4 H.sub.9 ##STR234##66 COOC.sub.4 H.sub.9 ##STR235##67 COOC.sub.4 H.sub.9 ##STR236##68 COOC.sub.4 H.sub.9 ##STR237##69 COOC.sub.4 H.sub.9 ##STR238##70 COOC.sub.4 H.sub.9 ##STR239##71 COOC.sub.4 H.sub.9 ##STR240##72 COOC.sub.4 H.sub.9 ##STR241##73 COOC.sub.4 H.sub.9 ##STR242##74 COOC.sub.4 H.sub.9 ##STR243##75 COOC.sub.4 H.sub.9 ##STR244##76 COOC.sub.4 H.sub.9 ##STR245##77 COOC.sub.4 H.sub.9 ##STR246##78 COOC.sub.4 H.sub.9 ##STR247##79 COOC.sub.4 H.sub.9 ##STR248##80 COOC.sub.4 H.sub.9 ##STR249##81 COOC.sub.4 H.sub.9 ##STR250##82 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR251##83 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR252##84 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR253##85 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR254##86 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR255##87 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR256##88 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR257##89 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR258##90 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR259##91 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR260##92 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR261##93 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR262##94 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR263##95 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR264##96 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR265##97 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR266##98 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR267##99 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR268##100 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR269##101 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR270##102 COOCH.sub.2 CH(CH.sub.3).sub.2 ##STR271##103 COOC.sub.3 H.sub.7 ##STR272##104 COOC.sub.3 H.sub.7 ##STR273##105 COOC.sub.3 H.sub.7 ##STR274##106 COOC.sub.3 H.sub.7 ##STR275##107 COOC.sub.3 H.sub.7 ##STR276##108 COOC.sub.3 H.sub.7 ##STR277##109 COOC.sub.3 H.sub.7 ##STR278##110 COOC.sub.3 H.sub.7 ##STR279##111 COOC.sub.3 H.sub.7 ##STR280##112 COOC.sub.3 H.sub.7 ##STR281##113 COOC.sub.3 H.sub.7 ##STR282##114 COOC.sub.3 H.sub.7 ##STR283##115 COOC.sub.3 H.sub.7 ##STR284##116 COOC.sub.3 H.sub.7 ##STR285##117 COOC.sub.3 H.sub.7 ##STR286##118 COOC.sub.3 H.sub.7 ##STR287##119 COOC.sub.3 H.sub.7 ##STR288##120 COOC.sub.3 H.sub.7 ##STR289##121 COOC.sub.3 H.sub.7 ##STR290##122 COOC.sub.3 H.sub.7 ##STR291##123 COOC.sub.3 H.sub.7 ##STR292##124 COOC.sub.3 H.sub.7 ##STR293##125 COOC.sub.3 H.sub.7 ##STR294##126 COOCH(CH.sub.3).sub.2 ##STR295##127 COOCH(CH.sub.3).sub.2 ##STR296##128 COOCH(CH.sub.3).sub.2 ##STR297##129 COOCH(CH.sub.3).sub.2 ##STR298##130 COOCH(CH.sub.3).sub.2 ##STR299##131 COOCH(CH.sub.3).sub.2 ##STR300##132 COOCH(CH.sub.3).sub.2 ##STR301##133 COOCH(CH.sub.3).sub.2 ##STR302##134 COOCH(CH.sub.3).sub.2 ##STR303##135 COOCH(CH.sub.3).sub.2 ##STR304##136 COOCH(CH.sub.3).sub.2 ##STR305##137 COOCH(CH.sub.3).sub.2 ##STR306##138 COOCH(CH.sub.3).sub.2 ##STR307##139 COOCH(CH.sub.3).sub.2 ##STR308##140 COOCH(CH.sub.3).sub.2 ##STR309##141 COOCH(CH.sub.3).sub.2 ##STR310##142 COOCH(CH.sub.3).sub.2 ##STR311##143 COOCH(CH.sub.3).sub.2 ##STR312##144 COOCH(CH.sub.3).sub.2 ##STR313##145 COOCH(CH.sub.3).sub.2 ##STR314##146 COOCH(CH.sub.3).sub.2 ##STR315##147 COOCH(CH.sub.3).sub.2 ##STR316##
TABLE 19__________________________________________________________________________ArCHC(COOR).sub.2 (3)Compound No. R Ar__________________________________________________________________________148 CH.sub.3 ##STR317##149 CH.sub.3 ##STR318##150 CH.sub.3 ##STR319##151 CH.sub.3 ##STR320##152 CH.sub.3 ##STR321##153 CH.sub.3 ##STR322##154 CH.sub.3 ##STR323##155 CH.sub.3 ##STR324##156 CH.sub.3 ##STR325##157 CH.sub.3 ##STR326##158 CH.sub.3 ##STR327##159 CH.sub.3 ##STR328##160 CH.sub.3 ##STR329##161 C.sub.4 H.sub.9 ##STR330##162 C.sub.4 H.sub.9 ##STR331##163 C.sub.4 H.sub.9 ##STR332##164 C.sub.4 H.sub.9 ##STR333##165 C.sub.4 H.sub.9 ##STR334##166 C.sub.4 H.sub.9 ##STR335##167 C.sub.4 H.sub.9 ##STR336##168 C.sub.4 H.sub.9 ##STR337##169 C.sub.4 H.sub.9 ##STR338##170 C.sub.4 H.sub.9 ##STR339##171 C.sub.4 H.sub.9 ##STR340##172 C.sub.4 H.sub.9 ##STR341##173 ##STR342## ##STR343##174 ##STR344## ##STR345##175 ##STR346## ##STR347##176 ##STR348## ##STR349##177 ##STR350## ##STR351##178 ##STR352## ##STR353##179 ##STR354## ##STR355##180 ##STR356## ##STR357##181 ##STR358## ##STR359##__________________________________________________________________________
TABLE 20______________________________________ ##STR360## (4)Compound No. Formula______________________________________ 1 ##STR361## 2 ##STR362## 3 ##STR363## 4 ##STR364## 5 ##STR365## 6 ##STR366## 7 ##STR367## 8 ##STR368## 9 ##STR369##10 ##STR370##11 ##STR371##12 ##STR372##13 ##STR373##14 ##STR374##15 ##STR375##16 ##STR376##17 ##STR377##18 ##STR378##19 ##STR379##20 ##STR380##21 ##STR381##22 ##STR382##23 ##STR383##24 ##STR384##25 ##STR385##26 ##STR386##27 ##STR387##28 ##STR388##29 ##STR389##30 ##STR390##31 ##STR391##32 ##STR392##33 ##STR393##34 ##STR394##35 ##STR395##36 ##STR396##______________________________________
TABLE 21______________________________________ArCHCHNO.sub.2 (5)Compound No. Ar______________________________________ 1 ##STR397## 2 ##STR398## 3 ##STR399## 4 ##STR400## 5 ##STR401## 6 ##STR402## 7 ##STR403## 8 ##STR404## 9 ##STR405##10 ##STR406##11 ##STR407##12 ##STR408##13 ##STR409##14 ##STR410##15 ##STR411##16 ##STR412##17 ##STR413##18 ##STR414##19 ##STR415##20 ##STR416##21 ##STR417##22 ##STR418##23 ##STR419##24 ##STR420##25 ##STR421##26 ##STR422##27 ##STR423##28 ##STR424##29 ##STR425##30 ##STR426##31 ##STR427##32 ##STR428##33 ##STR429##34 ##STR430##______________________________________
TABLE 22__________________________________________________________________________ ##STR431## (6)Compound No. R.sup.1 R.sup.2__________________________________________________________________________ 1 ##STR432## ##STR433## 2 ##STR434## ##STR435## 3 ##STR436## ##STR437## 4 ##STR438## ##STR439## 5 ##STR440## ##STR441## 6 ##STR442## ##STR443## 7 ##STR444## ##STR445## 8 ##STR446## ##STR447## 9 ##STR448## ##STR449##10 ##STR450## ##STR451##11 ##STR452## ##STR453##12 ##STR454## ##STR455##13 ##STR456## ##STR457##14 ##STR458## ##STR459##15 ##STR460## ##STR461##16 ##STR462## ##STR463##17 ##STR464## ##STR465##18 ##STR466## ##STR467##19 ##STR468## ##STR469##20 ##STR470## ##STR471##21 ##STR472## ##STR473##22 ##STR474## ##STR475##23 ##STR476## ##STR477##24 ##STR478## ##STR479##25 ##STR480## ##STR481##26 ##STR482## ##STR483##27 ##STR484## ##STR485##28 ##STR486## ##STR487##29 ##STR488## ##STR489##30 ##STR490## ##STR491##31 ##STR492## ##STR493##32 ##STR494## ##STR495##33 ##STR496## ##STR497##34 ##STR498## ##STR499##35 ##STR500## ##STR501##36 ##STR502## ##STR503##37 ##STR504## ##STR505##38 ##STR506## ##STR507##39 ##STR508## ##STR509##40 ##STR510## ##STR511##41 ##STR512## ##STR513##42 ##STR514## ##STR515##43 ##STR516## ##STR517##44 ##STR518## ##STR519##45 ##STR520## ##STR521##46 ##STR522## ##STR523##47 ##STR524## ##STR525##48 ##STR526## ##STR527##49 ##STR528## ##STR529##50 ##STR530## ##STR531##51 ##STR532## ##STR533##52 ##STR534## ##STR535##53 ##STR536## ##STR537##54 ##STR538## ##STR539##55 ##STR540## ##STR541##56 ##STR542## ##STR543##57 ##STR544## ##STR545##58 ##STR546## ##STR547##59 ##STR548## ##STR549##60 ##STR550## ##STR551##61 ##STR552## ##STR553##62 ##STR554## ##STR555##63 ##STR556## ##STR557##64 ##STR558## ##STR559##65 ##STR560## ##STR561##66 ##STR562## ##STR563##__________________________________________________________________________
TABLE 23______________________________________ ##STR564## (7)CompoundNo. R.sup.1 R.sup.2______________________________________ 1 H 4'-NO.sub.2 2 H 3'-NO.sub.2 3 H 3'-COOC.sub.2 H.sub.5 -4'-NO.sub.2 4 H 3'-NO.sub.2 -4'-F 5 H 3'-NO.sub.2 -4'-Cl 6 H 3'-NO.sub.2 -4'-CH.sub.3 7 H 4'-CN 8 H 3'-CN 9 H 3'-CF.sub.3 -4'-CN10 H 4'-Cl11 H 3'-Cl12 H 4'-Br13 H 3'-Br14 H 3'-Cl-4'-CH.sub.315 H 3'-CF.sub.3 -4'-F16 H 3'-CF.sub.3 -4'-Cl17 H 3'-Cl-4'-F18 H 3',4'-diF19 H 3',4'-diCl20 H 3',5'-diCl21 H 2',4',5'-triCl22 H 4'-COOC.sub.2 H.sub.523 H 4'-COOC.sub.4 H.sub.924 H 4'-CONHC.sub.4 H.sub.925 H 4'-CON(C.sub.4 H.sub.9).sub.226 H 3'-CF.sub.327 H 4'-CF.sub.328 H 4'-CH.sub.329 H 4'-C.sub.2 H.sub.530 H 4'-C.sub.4 H.sub.931 H 4'-C.sub.6 H.sub.1332 H ##STR565##33 H 3',4'-diCH.sub.334 H H35 Cl 4'-NO.sub.236 Cl 3'-NO.sub.237 Cl 3'-NO.sub.2 -4'-CH.sub.338 Cl 4'-CN39 Cl 4'-Cl40 Cl 3'-CF.sub.3 -4'-F41 Cl 3',4'-diCl42 Cl 4'-COOC.sub.2 H.sub.543 Cl 4'-CF.sub.344 Cl 4'-C.sub.4 H.sub.945 Br 4'-NO.sub.246 Br 4'-CN47 Br 4'-COOC.sub.2 H.sub.548 Br 4'-CF.sub.349 ##STR566## 4'-NO.sub.250 ##STR567## 3'-NO.sub.251 ##STR568## 3'-NO.sub.2 -4'-CH.sub.352 ##STR569## 4'-CN53 ##STR570## 4'-Cl54 ##STR571## 3',4'-diCl55 ##STR572## 4'-COOC.sub.2 H.sub.556 ##STR573## 4'-COOC.sub.4 H.sub.957 ##STR574## 4'-COON(C.sub.4 H.sub.9).sub.258 ##STR575## 4'-CF.sub.359 ##STR576## 4'-C.sub.2 H.sub.560 ##STR577## 4'-C.sub.4 H.sub.961 ##STR578## H62 ##STR579## 4'-NO.sub.263 ##STR580## 4'-COOC.sub.2 H.sub.564 ##STR581## 4'-COOC.sub.4 H.sub.965 ##STR582## 4'-Cl66 ##STR583## 4'-CF.sub.367 ##STR584## 4'-C.sub.4 H.sub.968 CH.sub.3 4'-NO.sub.269 CH.sub.3 4'-CN70 CH.sub.3 4'-Cl71 CH.sub.3 4'-COOC.sub.2 H.sub.572 CH.sub.3 4'-COOC.sub.4 H.sub.973 CH.sub.3 4'-CF.sub.374 CH.sub.3 4'-C.sub.2 H.sub.575 CH.sub.3 4'-C.sub.4 H.sub.9______________________________________
TABLE 24______________________________________ ##STR585## (8)Compound No. R.sup.3______________________________________76 4'-NO.sub.277 3'-NO.sub.278 4'-CN79 4'-Cl80 3'-Cl81 4'-COOC.sub.2 H.sub.582 4'-COOC.sub.4 H.sub.983 4'-CF.sub.384 4'-C.sub.2 H.sub.585 4'-C.sub.4 H.sub.986 4'-C.sub.6 H.sub.1387 H______________________________________
TABLE 25______________________________________ ##STR586## (9)Com-poundNo. R.sup.1 R.sup.2______________________________________ 1 ##STR587## ##STR588## 2 ##STR589## ##STR590## 3 ##STR591## ##STR592## 4 ##STR593## ##STR594## 5 ##STR595## ##STR596## 6 ##STR597## ##STR598## 7 ##STR599## ##STR600## 8 ##STR601## ##STR602## 9 ##STR603## ##STR604##10 ##STR605## ##STR606##11 ##STR607## ##STR608##12 ##STR609## ##STR610##13 ##STR611## ##STR612##14 ##STR613## ##STR614##15 ##STR615## ##STR616##16 ##STR617## ##STR618##17 ##STR619## ##STR620##18 ##STR621## ##STR622##19 ##STR623## ##STR624##20 ##STR625## ##STR626##21 ##STR627## ##STR628##22 ##STR629## ##STR630##23 ##STR631## ##STR632##24 ##STR633## ##STR634##25 ##STR635## ##STR636##26 ##STR637## ##STR638##27 ##STR639## ##STR640##28 ##STR641## ##STR642##29 ##STR643## ##STR644##30 ##STR645## ##STR646##31 ##STR647## ##STR648##32 ##STR649## ##STR650##33 ##STR651## ##STR652##34 ##STR653## ##STR654##35 ##STR655## ##STR656##36 ##STR657## ##STR658##37 ##STR659## ##STR660##38 ##STR661## ##STR662##39 ##STR663## ##STR664##40 ##STR665## ##STR666##41 ##STR667## ##STR668##42 ##STR669## ##STR670##43 ##STR671## ##STR672##44 ##STR673## ##STR674##45 ##STR675## ##STR676##46 ##STR677## ##STR678##47 ##STR679## ##STR680##48 ##STR681## ##STR682##49 ##STR683## ##STR684##50 ##STR685## ##STR686##51 ##STR687## ##STR688##52 ##STR689## ##STR690##53 ##STR691## ##STR692##54 ##STR693## ##STR694##55 ##STR695## ##STR696##56 ##STR697## ##STR698##57 ##STR699## ##STR700##58 ##STR701## ##STR702##59 ##STR703## ##STR704##60 ##STR705## ##STR706##61 ##STR707## ##STR708##62 ##STR709## ##STR710##63 ##STR711## ##STR712##64 ##STR713## ##STR714##65 ##STR715## ##STR716##66 ##STR717## ##STR718##67 ##STR719## ##STR720##68 ##STR721## ##STR722##69 ##STR723## ##STR724##70 ##STR725## ##STR726##71 ##STR727## ##STR728##72 ##STR729## ##STR730##73 ##STR731## ##STR732##74 ##STR733## ##STR734##75 ##STR735## ##STR736##76 ##STR737## ##STR738##77 ##STR739## ##STR740##78 ##STR741## ##STR742##79 ##STR743## ##STR744##80 ##STR745## ##STR746##81 ##STR747## ##STR748##82 ##STR749## ##STR750##83 ##STR751## ##STR752##84 ##STR753## ##STR754##85 ##STR755## ##STR756##86 ##STR757## ##STR758##87 ##STR759## ##STR760##88 ##STR761## ##STR762##89 ##STR763## ##STR764##90 ##STR765## ##STR766##91 ##STR767## ##STR768##92 ##STR769## ##STR770##93 ##STR771## ##STR772##94 ##STR773## ##STR774##95 ##STR775## ##STR776##96 ##STR777## ##STR778##97 ##STR779## ##STR780##98 ##STR781## ##STR782##99 ##STR783## ##STR784##100 ##STR785## ##STR786##101 ##STR787## ##STR788##102 ##STR789## ##STR790##103 ##STR791## ##STR792##104 ##STR793## ##STR794##105 ##STR795## ##STR796##106 ##STR797## ##STR798##107 ##STR799## ##STR800##108 ##STR801## ##STR802##109 ##STR803## ##STR804##110 ##STR805## ##STR806##111 ##STR807## ##STR808##112 ##STR809## ##STR810##113 ##STR811## ##STR812##114 ##STR813## ##STR814##115 ##STR815## ##STR816##116 ##STR817## ##STR818##117 ##STR819## ##STR820##118 ##STR821## ##STR822##119 ##STR823## ##STR824##120 ##STR825## ##STR826##121 ##STR827## ##STR828##122 ##STR829## ##STR830##123 ##STR831## ##STR832##124 ##STR833## ##STR834##125 ##STR835## ##STR836##126 ##STR837## ##STR838##127 ##STR839## ##STR840##128 ##STR841## ##STR842##129 ##STR843## ##STR844##130 ##STR845## ##STR846##131 ##STR847## ##STR848##132 ##STR849## ##STR850##133 ##STR851## ##STR852##134 ##STR853## ##STR854##135 ##STR855## ##STR856##136 ##STR857## ##STR858##137 ##STR859## ##STR860##138 ##STR861## ##STR862##139 ##STR863## ##STR864##140 ##STR865## ##STR866##141 ##STR867## ##STR868##142 ##STR869## ##STR870##143 ##STR871## ##STR872##144 ##STR873## ##STR874##145 ##STR875## ##STR876##146 ##STR877## ##STR878##147 ##STR879## ##STR880##148 ##STR881## ##STR882##149 ##STR883## ##STR884##150 ##STR885## ##STR886##151 ##STR887## ##STR888##152 ##STR889## ##STR890##153 ##STR891## ##STR892##154 ##STR893## ##STR894##155 ##STR895## ##STR896##156 ##STR897## ##STR898##157 ##STR899## ##STR900##158 ##STR901## ##STR902##159 ##STR903## ##STR904##160 ##STR905## ##STR906##161 ##STR907## ##STR908##162 ##STR909## ##STR910##163 ##STR911## ##STR912##164 ##STR913## ##STR914##165 ##STR915## ##STR916##166 ##STR917## ##STR918##167 ##STR919## ##STR920##168 ##STR921## ##STR922##169 ##STR923## ##STR924##170 ##STR925## ##STR926##171 ##STR927## ##STR928##172 ##STR929## ##STR930##173 ##STR931## ##STR932##174 ##STR933## ##STR934##175 ##STR935## ##STR936##176 ##STR937## ##STR938##______________________________________
TABLE 26__________________________________________________________________________ ##STR939##CompoundNo. R.sup.1 R.sup.2__________________________________________________________________________ 1 4-COOCH.sub.3 H 2 4-COOCH.sub.3 7-NO.sub.2 3 2-C(CH.sub.3).sub.3 -4-NO.sub.2 5-NO.sub.2 -7-NO.sub.2 4 4-COOC.sub.2 H.sub.5 H 5 2-COOC.sub.4 H.sub.9 H 6 4-COOC.sub.4 H.sub.9 H 7 4-COOC.sub.8 H.sub.17 H 8 2-C(CH.sub.3).sub.3 -4-COOC.sub.4 H.sub.9 7-C(CH.sub.3).sub.3 9 ##STR940## H10 ##STR941## H11 2,4-di-NO.sub.2 7-NO.sub.212 ##STR942## H13 ##STR943## H14 ##STR944## H15 2-CH.sub.3 7-CH.sub.3__________________________________________________________________________
TABLE 27______________________________________ ##STR945##CompoundNo. R.sup.3 R.sup.4______________________________________ 1 H H 2 4-NO.sub.2 H 3 3-NO.sub.2 H 4 4-NO.sub.2 4'-CH.sub.3 5 H 2'-CH.sub.3 6 4-NO.sub.2 4'-OCH.sub.3 7 4-NO.sub.2 ##STR946## 8 4-NO.sub.2 ##STR947## 9 4-CH.sub.3 4'-CH.sub.310 2,4-di-NO.sub.2 H11 H ##STR948##12 4-Cl 4'-Cl13 H 3'-COOC.sub.4 H.sub.914 3-NO.sub.2 4'-COOC.sub.4 H.sub.915 4-NO.sub.2 ##STR949##16 4-NO.sub.2 4'-I17 4-CN 4'-NO.sub.218 4-CN 4'-COOC.sub.4 H.sub.919 4,5-di-COOC.sub.2 H.sub.5 3',4'-di-COOC.sub.2 H.sub.520 3-NO.sub.2 -4-C.sub.4 H.sub.9 3'-NO.sub.2 -4'-C.sub.4 H.sub.921 4-NO.sub.2 ##STR950##22 H ##STR951##23 4-NO.sub.2 H______________________________________
TABLE 28__________________________________________________________________________ ##STR952##CompoundNo. R.sup.5 R.sup.6__________________________________________________________________________ 1 4-COOCH.sub.3 H 2 4-COOCH.sub.3 7-NO.sub.2 3 2-C(CH.sub.3).sub.3 -4-NO.sub.2 5-NO.sub.2 -7-NO.sub.2 4 4-COOC.sub.2 H.sub.5 H 5 2-COOC.sub.4 H.sub.9 H 6 4-COOC.sub.4 H.sub.9 H 7 4-COOC.sub.8 H.sub.17 H 8 2-C(CH.sub.3).sub.3 -4-COOC.sub.4 H.sub.9 7-C(CH.sub.3).sub.3 9 ##STR953## H10 ##STR954## H11 2,4-di-NO.sub.2 7-NO.sub.212 ##STR955## H13 ##STR956## H14 ##STR957## H15 2-CH.sub.3 7-CH.sub.3__________________________________________________________________________
TABLE 29______________________________________ ##STR958##CompoundNo. R.sup.7 R.sup.8______________________________________ 1 H H 2 4-NO.sub.2 H 3 3-NO.sub.2 H 4 4-NO.sub.2 4'-CH.sub.3 5 H 2'-CH.sub.3 6 4-NO.sub.2 4'-OCH.sub.3 7 4-NO.sub.2 ##STR959## 8 4-NO.sub.2 ##STR960## 9 4-CH.sub.3 4'-CH.sub.310 2,4-di-NO.sub.2 H11 H ##STR961##12 4-Cl 4'-Cl13 H 3'-COOC.sub.4 H.sub.914 3-NO.sub.2 4'-COOC.sub.4 H.sub.915 4-NO.sub.2 ##STR962##16 4-NO.sub.2 4'-I17 4-CN 4'-NO.sub.218 4-CN 4'-COOC.sub.4 H.sub.919 4,5-di-COOC.sub.2 H.sub.5 3',4'-di-COOC.sub.2 H.sub.520 3-NO.sub.2 -4-C.sub.4 H.sub.9 3'-NO.sub.2 -4'-C.sub.4 H.sub.921 4-NO.sub.2 ##STR963##22 H ##STR964##23 4-NO.sub.2 H______________________________________
TABLE 30______________________________________ ##STR965##CompoundNo. R______________________________________ 1 ##STR966## 2 ##STR967## 3 ##STR968## 4 ##STR969## 5 ##STR970## 6 ##STR971## 7 ##STR972## 8 ##STR973## 9 ##STR974##10 ##STR975##11 ##STR976##12 ##STR977##13 ##STR978##14 ##STR979##15 ##STR980##16 ##STR981##17 ##STR982##18 ##STR983##19 ##STR984##20 ##STR985##21 ##STR986##22 ##STR987##23 ##STR988##24 ##STR989##25 ##STR990##26 ##STR991##27 ##STR992##28 ##STR993##29 ##STR994##30 ##STR995##31 ##STR996##32 ##STR997##33 ##STR998##34 ##STR999##35 ##STR1000##36 ##STR1001##37 ##STR1002##38 ##STR1003##39 ##STR1004##40 ##STR1005##41 ##STR1006##42 ##STR1007##43 ##STR1008##44 ##STR1009##45 ##STR1010##46 ##STR1011##______________________________________
Furthermore, when at least one organic acceptor compound of formula (A), (B) or (C) is employed in the single-layered photoconductive layer, not only the sensitizing effect is improved, but also the decrease of the charging characteristics can be prevented during the repeated operations and the charging stability is remarkably improved.
[Organic Acceptor Compound of Formula (A)] ##STR1012## wherein R.sup.1, R.sup.2, and R.sup.3 each is hydrogen, a substituted or unsubstituted alkyl group, an alkoxyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonamide group, a substituted or unsubstituted carbamoyl group, a halogen atom, cyano group, or nitro group, and R.sup.1 may form a ring in combination with other atoms; k, l and m each is an integer of 1 to 4; and X is oxygen, sulfur or selenium.
[Organic Acceptor Compound of Formula (B)] ##STR1013## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be the same or different, and each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, cyano group, or nitro group; and X is ##STR1014## in which R.sup.5 and R.sup.6 may be the same or different and each is hydrogen, a halogen atom, cyano group, a substituted or unsubstituted aromatic group, or --COOR.sup.7 in which R.sup.7 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group; or
N--R.sup.8, in which R.sup.8 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, or cyano group.
[Organic Acceptor Compound of Formula (C)] ##STR1015## wherein R.sup.1 may be the same or different, and is a halogen atom, nitro group, or a substituted or unsubstituted alkyl group; X is .dbd.O, N--R.sup.2,
in which R.sup.2 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, or ##STR1016## in which R.sup.3 and R.sup.4 may be the same or different and each is hydrogen, cyano group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted phenoxycarbonyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group; and
p is an integer of 0 to 4, provided that when X is oxygen, p is an integer of 1 to 4.
TABLES 31-32 show specific examples of the organic acceptor compound of formulae (A) and (B), and TABLES 33-35 show specific examples of the organic acceptor compounds of formula (C).
TABLE 31______________________________________ ##STR1017##CompoundNo. k l m X.sup.3 R.sup.14 R.sup.15 R.sup.16______________________________________A-1 0 0 1 S H H 2-COOC.sub.4 H.sub.9A-2 0 0 1 S H H 4-COOC.sub.4 H.sub.9A-3 0 0 1 S H H 1-COOC.sub.4 H.sub.9A-4 0 0 1 S H H 3-COOC.sub.4 H.sub.9A-5 0 0 1 S H H 1-COOCH.sub.3A-6 0 0 1 S H H 2-COOC.sub.5 H.sub.11A-7 0 0 1 S H H 3-COOC.sub.5 H.sub.11A-8 0 0 1 S H H 4-COOC.sub.5 H.sub.11A-9 0 0 1 S H H 1-COOC.sub.6 H.sub.13A-10 0 0 1 S H H 2-COOC.sub.6 H.sub.13A-11 0 0 1 S H H 3-COOC.sub.6 H.sub.13A-12 0 0 1 S H H 4-COOC.sub.6 H.sub.13A-13 0 0 1 S H H 1-COOC.sub.7 H.sub.15A-14 0 0 1 S H H 2-COOC.sub.7 H.sub.15A-15 0 0 1 S H H 3-COOC.sub.7 H.sub.15A-16 0 0 1 S H H 4-COOC.sub.7 H.sub.15A-17 0 0 1 S H H 1-COOC.sub.8 H.sub.17A-18 0 0 1 S H H 2-COOC.sub.8 H.sub.17A-19 0 0 1 S H H 3-COOC.sub.8 H.sub.17A-20 0 0 1 S H H 4-COOC.sub.8 H.sub.17A-21 0 0 1 O H H 2-COOC.sub.4 H.sub.9A-22 0 0 1 O H H 4-COOC.sub.4 H.sub.9A-23 0 0 1 O H H 1-COOC.sub.4 H.sub.9A-24 0 0 1 O H H 3-COOC.sub.4 H.sub.9A-25 0 0 1 O H H 1-COOCH.sub.3A-26 0 0 1 O H H 2-COOCH.sub.3A-27 0 0 1 O H H 3-COOCH.sub.3A-28 0 0 1 O H H 4-COOCH.sub.3A-29 0 0 1 O H H 1-COOC.sub.2 H.sub.5A-30 1 0 1 O 2-NO.sub.2 H 2-COOC.sub.7 H.sub.15A-31 1 0 1 O 2-NO.sub.2 H 3-COOC.sub.7 H.sub.15A-32 1 0 1 O 2-NO.sub.2 H 4-COOC.sub.7 H.sub.15A-33 1 0 1 O 2-NO.sub.2 H 1-COOC.sub.8 H.sub.17A-34 1 0 1 O 2-NO.sub.2 H 2-COOC.sub.8 H.sub.17A-35 1 0 1 O 2-NO.sub.2 H 3-COOC.sub.8 H.sub.17A-36 1 0 1 O 2-NO.sub.2 H 4-COOC.sub.8 H.sub.17A-37 1 0 1 O 3-C(CH.sub.3).sub.3 H 2-COOC.sub.4 H.sub.9A-38 1 0 1 O 3-C(CH.sub.3).sub.3 H 4-COOC.sub.4 H.sub.9A-39 1 0 1 O 3-C(CH.sub.3).sub.3 H 1-COOC.sub.4 H.sub.9A-40 1 0 1 O 3-C(CH.sub.3).sub.3 H 3-COOC.sub.4 H.sub.9A-41 1 0 1 O 3-C(CH.sub.3).sub.3 H 1-COOCH.sub.3A-42 0 1 1 S H 6-CF.sub.3 3-CF.sub.3A-43 0 1 2 S H 7-CF.sub.3 2-CF.sub.3 4-C.sub.4 H.sub.9A-44 0 1 2 S H 7-CF.sub.3 2-NO.sub.2 4-C.sub.8 H.sub.17A-45 0 1 2 S H 7-NO.sub.2 2-NO.sub.2 4-NO.sub.2A-46 0 2 2 S H 7-NO.sub.2 2-NO.sub.2 5-NO.sub.2 4-NO.sub.2A-47 0 0 1 S H H 2-NO.sub.2A-48 0 1 1 S H 7-NO.sub.2 2-NO.sub.2A-49 0 1 1 O H 7-CN 4-COC.sub.8 H.sub.17A-50 0 1 1 O H 7-CN 4-COOC.sub.4 H.sub.9A-51 0 1 1 O H 7-CN 4-OC.sub.4 H.sub.9______________________________________
TABLE 32__________________________________________________________________________ ##STR1018##Compound No. X.sup.4 R.sup.17 R.sup.18 R.sup.19 R.sup.20__________________________________________________________________________B-1 O H H H HB-2 ##STR1019## H H H HB-3 ##STR1020## H H H HB-4 ##STR1021## H H H HB-5 ##STR1022## H H H HB-6 ##STR1023## H H H HB-7 ##STR1024## H H H HB-8 ##STR1025## H H H HB-9 ##STR1026## H H H HB-10 ##STR1027## H H H HB-11 ##STR1028## H H H HB-12 ##STR1029## H H H HB-13 ##STR1030## H H H HB-14 ##STR1031## H H H HB-15 ##STR1032## H H H HB-16 ##STR1033## H H H HB-17 ##STR1034## H H H HB-18 ##STR1035## H H H HB-19 ##STR1036## H H H HB-20 ##STR1037## H H H HB-21 ##STR1038## H H H HB-22 ##STR1039## H H H HB-23 ##STR1040## H H H HB-24 ##STR1041## H H H HB-25 ##STR1042## H H H HB-26 ##STR1043## H H H HB-27 O 4-CH.sub.3 H 2-CH.sub.3 HB-28 ##STR1044## 4-CH.sub.3 H 2-CH.sub.3 HB-29 ##STR1045## 4-CH.sub.3 H 2-CH.sub.3 HB-30 O 4-CH.sub.3 4-CH.sub.3 2-CH.sub.3 HB-31 ##STR1046## 4-CH.sub.3 4-CH.sub.3 2-CH.sub.3 HB-32 ##STR1047## 4-CH.sub.3 4-CH.sub.3 2-CH.sub.3 HB-33 ##STR1048## 4-C.sub.4 H.sub.9 H 2-CH.sub.3 HB-34 ##STR1049## 3-CH.sub.3 H 3-C.sub.4 H.sub.9 HB-35 ##STR1050## 4-CF.sub.3 H H HB-36 ##STR1051## 4-Br H 3-Br 4-BrB-37 ##STR1052## 4-NO.sub.2 H H HB-38 ##STR1053## 4-CN H H HB-39 O H H 2-NO.sub.2 HB-40 ##STR1054## 4-Br H 2-Br HB-41 ##STR1055## 4-Cl H H HB-42 ##STR1056## H H 2-Br H__________________________________________________________________________
TABLE 33______________________________________ ##STR1057##X.sup.5 : = OCompound No. P R.sup.23______________________________________CI-1 1 CH.sub.3CI-2 1 CF.sub.3CI-3 1 NO.sub.2CI-4 2 ClCI-5 2 CH.sub.3______________________________________
TABLE 34______________________________________ ##STR1058##Compound No. P R.sup.23 R.sup.24______________________________________CII-1 0 -- ##STR1059##CII-2 0 -- ##STR1060##CII-3 0 -- ##STR1061##CII-4 0 -- ##STR1062##CII-5 0 -- ##STR1063##CII-6 0 -- ##STR1064##CII-7 0 -- ##STR1065##CII-8 0 -- ##STR1066##CII-9 0 -- ##STR1067##CII-10 0 -- ##STR1068##CII-11 0 -- ##STR1069##CII-12 0 -- ##STR1070##CII-13 0 -- ##STR1071##CII-14 0 -- ##STR1072##CII-15 0 -- ##STR1073##CII-16 0 -- ##STR1074##CII-17 0 -- ##STR1075##CII-18 0 -- ##STR1076##CII-19 0 -- ##STR1077##CII-20 0 -- ##STR1078##CII-21 0 -- ##STR1079##CII-22 0 -- ##STR1080##CII-23 0 -- ##STR1081##CII-24 1 CF.sub.3 ##STR1082##CII-25 1 CF.sub.3 ##STR1083##CII-26 1 CF.sub.3 ##STR1084##CII-27 1 CF.sub.3 ##STR1085##CII-28 1 CF.sub.3 ##STR1086##CII-29 1 CF.sub.3 ##STR1087##CII-30 1 CF.sub.3 ##STR1088##CII-31 1 NO.sub.2 ##STR1089##CII-32 1 NO.sub.2 ##STR1090##CII-33 1 NO.sub.2 ##STR1091##CII-34 1 NO.sub.2 ##STR1092##CII-35 1 NO.sub.2 ##STR1093##CII-36 1 NO.sub.2 ##STR1094##CII-37 2 CH.sub.3 ##STR1095##CII-38 2 CH.sub.3 ##STR1096##CII-39 2 CH.sub.3 ##STR1097##CII-40 2 CH.sub.3 ##STR1098##CII-41 2 CH.sub.3 ##STR1099##CII-42 2 Cl ##STR1100##CII-43 2 Cl ##STR1101##CII-44 2 Cl ##STR1102##CII-45 2 Cl ##STR1103##______________________________________
TABLE 35__________________________________________________________________________ ##STR1104##Compound No. P R.sup.23 R.sup.25 R.sup.26__________________________________________________________________________CIII-1 0 -- H CNCIII-2 0 -- H COOC.sub.2 H.sub.5CIII-3 0 -- H COOC.sub.4 H.sub.9CIII-4 0 -- H ##STR1105##CIII-5 0 -- H ##STR1106##CIII-6 0 -- H ##STR1107##CIII-7 0 -- CN CNCIII-8 0 -- CN COOCH.sub.3CIII-9 0 -- CN COOC.sub.2 H.sub.5CIII-10 0 -- CN COOC.sub.3 H.sub.7CIII-11 0 -- CN COOC.sub.4 H.sub.9CIII-12 0 -- CN COOC.sub.5 H.sub.11CIII-13 0 -- CN COOC.sub.6 H.sub.13CIII-14 0 -- CN COOC.sub.7 H.sub.15CIII-15 0 -- CN COOC.sub.8 H.sub.17CIII-16 0 -- CN COOCF.sub.3CIII-17 0 -- CN COOCH(CF.sub.3).sub.2CIII-18 0 -- CN COOCH.sub.2 OCH.sub.3CIII-19 0 -- CN COOC.sub.2 H.sub.4 OCH.sub.3CIII-20 0 -- CN ##STR1108##CIII-21 0 -- CN ##STR1109##CIII-22 0 -- CN ##STR1110##CIII-23 0 -- CN ##STR1111##CIII-24 0 -- CN ##STR1112##CIII-25 0 -- CN ##STR1113##CIII-26 0 -- CN ##STR1114##CIII-27 0 -- CN ##STR1115##CIII-28 0 -- CN ##STR1116##CIII-29 0 -- CN ##STR1117##CIII-30 0 -- CN ##STR1118##CIII-31 0 -- CN ##STR1119##CIII-32 0 -- CN ##STR1120##CIII-33 0 -- CN ##STR1121##CIII-34 0 -- CN ##STR1122##CIII-35 0 -- CN ##STR1123##CIII-36 0 -- CN ##STR1124##CIII-37 0 -- CN ##STR1125##CIII-38 0 -- CN ##STR1126##CIII-39 0 -- CN ##STR1127##CIII-40 0 -- CN ##STR1128##CIII-41 0 -- CN ##STR1129##CIII-42 0 -- CN ##STR1130##CIII-43 0 -- CN ##STR1131##CIII-44 0 -- CN ##STR1132##CIII-45 0 -- CN ##STR1133##CIII-46 0 -- COOCH.sub.3 COOCH.sub.3CIII-47 0 -- COOCH.sub.3 ##STR1134##CIII-48 0 -- COOC.sub.2 H.sub.5 COOC.sub.2 H.sub.5CIII-49 0 -- COOCH(CH.sub.3).sub.2 COOCH(CH.sub.3).sub.2CIII-50 0 -- COOC.sub.4 H.sub.9 COOC.sub.4 H.sub.9CIII-51 0 -- ##STR1135## ##STR1136##CIII-52 1 CF.sub.3 H CNCIII-53 1 CF.sub.3 H COOC.sub.4 H.sub.9CIII-54 1 CF.sub.3 H ##STR1137##CIII-55 1 CF.sub.3 CN CNCIII-56 1 CF.sub.3 CN COOC.sub.2 H.sub.5CIII-57 1 CF.sub.3 CN COOC.sub.4 H.sub.9CIII-58 1 CF.sub.3 CN COOC.sub.6 H.sub.13CIII-59 1 CF.sub.3 CN COOC.sub.8 H.sub.17CIII-60 1 CF.sub.3 CN ##STR1138##CIII-61 1 CF.sub.3 CN ##STR1139##CIII-62 1 CF.sub.3 CN ##STR1140##CIII-63 1 CF.sub.3 COOC.sub.2 H.sub.5 COOC.sub.2 H.sub.5CIII-64 1 CF.sub.3 COOC.sub.4 H.sub.9 COOC.sub.4 H.sub.9CIII-65 1 NO.sub.2 CN CNCIII-66 1 NO.sub.2 CN COOC.sub.4 H.sub.9CIII-67 1 NO.sub.2 CN COOC.sub.6 H.sub.13CIII-68 1 NO.sub.2 CN COOC.sub.8 H.sub.17CIII-69 1 NO.sub.2 CN ##STR1141##CIII-70 I NO.sub.2 CN ##STR1142##CIII-71 1 NO.sub.2 COOC.sub.2 H.sub.5 COOC.sub.2 H.sub.5CIII-72 1 NO.sub.2 COOC.sub.4 H.sub.9 COOC.sub.4 H.sub.9CIII-73 2 CH.sub.3 CN CNCIII-74 2 CH.sub.3 CN COOC.sub.4 H.sub.9CIII-75 2 CH.sub.3 CN COOC.sub.6 H.sub.13CIII-76 2 CH.sub.3 CN COOC.sub.8 H.sub.17CIII-77 2 CH.sub.3 CN ##STR1143##CIII-78 2 CH.sub.3 CN ##STR1144##CIII-79 2 CH.sub.3 COOC.sub.2 H.sub.5 COOC.sub.2 H.sub.5CIII-80 2 CH.sub.3 COOC.sub.4 H.sub.9 COOC.sub.4 H.sub.9CIII-81 2 Cl CN CNCIII-82 2 Cl CN COOC.sub.4 H.sub.9CIII-83 2 Cl CN COOC.sub.6 H.sub.13CIII-84 2 Cl CN COOC.sub.8 H.sub.17CIII-85 2 Cl CN ##STR1145##CIII-86 2 Cl CN ##STR1146##CIII-87 2 Cl COOC.sub.2 H.sub.5 COOC.sub.2 H.sub.5CIII-88 2 Cl COOC.sub.4 H.sub.9 COOC.sub.4 H.sub.9__________________________________________________________________________
It is also preferable that the organic acceptor compound for use in the present invention have a reduction potential in a range of -0.2 to -1.2 V (vs SCE).
As organic acceptor compounds having a reduction potential in the above-mentioned range, derivatives of benzoquinone, naphthoquinone, anthraquinone, diphenoquinone; anhydrides; and aliphatic compounds, aromatic compound, and heterocyclic compounds, which have an electron attractive group such as nitro group, nitroso group, or cyano group, can be given.
The reduction potential of such organic acceptor compounds for use in the present invention is a half-wave potential obtained by conventionally known cyclic voltametry, using acetonitrile as a solvent, 0.1 MTEAP as an electrolyte, and a saturated calomel electrode (SCE) as a reference electrode.
The reasons why it is preferable that the organic acceptor compound for use in the present invention have a reduction potential in a range of -0.2 to -1.2 V (vs SCE) are that the reduction potential corresponds to the affinity for electrons, and that organic acceptor compounds with a reduction potential in the above-mentioned range have excellent electron transporting performance, so that when the organic acceptor compounds with a reduction potential in the above-mentioned range are employed in combination with the disazo compound and trisazo compound having the previously mentioned respective chemical structures, which are used as charge generating materials, excellent electrophotographic characteristics are exhibited.
The above-mentioned organic acceptor compounds can be used alone or in combination.
Furthermore in the present invention, to improve the charging stability of the single-layered photoconductive layer during the repeated use thereof, the photoconductive layer may further comprise an antioxidant.
More specifically, any conventional antioxidants can be employed. Specific examples of such antioxidants include antioxidants for plastics, rubber, petroleum, and fats and oils; ultraviolet absorbers; and light stabilizers such as phenol and phenol derivatives, paraphenylenediamines, hydroquinone and derivatives thereof, organic sulfur-containing compounds, organic phosphorus-containing compounds, hydroxy anisoles, piperidine and oxopiperidine, carotenes, amines, tocophenols, Ni(II) complexes, and sulfides, as disclosed in Japanese Laid-Open Patent Applications 57-122444, 60-188956, 63-18355, and 63-18356.
In particular, It is preferable that such an antioxidant for use in the present invention comprise at least one compound selected from the group consisting of compounds of formulae (I) to (XII):
[Compound of Formula (I)] ##STR1147## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is hydrogen, a halogen atom, hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted amino group, imino group, a heterocyclic group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
[Compound of Formula (II)] ##STR1148## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an acyl group, an alkylacylamino group, an arylacylamino group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfonamide group, an arylsulfonamide group, an alkylsulfamoyl group, an arylsulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an alkylacyloxy group, an arylacyloxy group, a silyl group, or a heterocyclic group, provided that at least one of R.sup.1, R.sup.2, R.sup.3 or R.sup.4 is a group having 4 or more carbon atoms.
[Compound of Formula (III)] ##STR1149## wherein R.sup.1 to R.sup.8 each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
[Compound of Formula (IV)] ##STR1150## wherein R.sup.1 to R.sup.7 each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
[Compound of Formula (V)] ##STR1151## wherein R.sup.1 to R.sup.7 each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
[Compound of Formula (VI)] ##STR1152## wherein R.sup.1 to R.sup.6 each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
[Compound of Formula (VII)] ##STR1153## wherein R.sup.1 to R.sup.8 each is hydrogen, a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted phosphonyl group, or a substituted or unsubstituted carbamoyl group.
[Compound of Formula (VIII)] ##STR1154## [Compound of Formula (IX)] ##STR1155## wherein R.sup.1 to R.sup.10 and R.sup.11 to R.sup.18 each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
[Compound of Formula (X)] ##STR1156## [Compound of Formula (XI)] ##STR1157## wherein R.sup.1 to R.sup.8 and R.sup.9 to R.sup.18 each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
[Compound of Formula (XII)] ##STR1158## wherein R.sup.1 to R.sup.5 each is hydrogen, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, a substituted amino group, an imino group, a heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a sulfoxide group, a sulfonyl group, an acyl group, or an azo group.
These antioxidants can be obtained by the synthesis in accordance with the methods described in U.S. Pat. No. 1,968,906 and J. Am. Chem. Soc. 55. 1224 (1933).
It is preferable that the amount of the antioxidant in the photoconductive layer be in the range of 0.01 to 2 parts by weight to 10 parts by weight of the binder resin. When the amount of the antioxidant is within the above range, the charging stability is sufficiently improved, with the decrease of photosensitivity and the increase of the residual potential being prevented.
TABLES 36 to 47 respectively show specific examples of the compounds of formulae (I) to (XII) serving as antioxidant component for use in the present invention.
TABLE 36______________________________________ ##STR1159## (I)-1 ##STR1160## (I)-2 ##STR1161## (I)-3 ##STR1162## (I)-4 ##STR1163## (I)-5 ##STR1164## (I)-6 ##STR1165## (I)-7 ##STR1166## (I)-8 ##STR1167## (I)-9 ##STR1168## (I)-10 ##STR1169## (I)-11 ##STR1170## (I)-12 ##STR1171## (I)-13 ##STR1172## (I)-14 ##STR1173## (I)-15______________________________________
TABLE 37__________________________________________________________________________ ##STR1174## (II)-1 ##STR1175## (II)-2 ##STR1176## (II)-3 ##STR1177## (II)-4 ##STR1178## (II)-5 ##STR1179## (II)-6 ##STR1180## (II)-7 ##STR1181## (II)-8 ##STR1182## (II)-9 ##STR1183## (II)-10 ##STR1184## (II)-11 ##STR1185## (II)-12 ##STR1186## (II)-13 ##STR1187## (II)-14 ##STR1188## (II)-15 ##STR1189## (II)-16 ##STR1190## (II)-17 ##STR1191## (II)-18 ##STR1192## (II)-19 ##STR1193## (II)-20 ##STR1194## (II)-21 ##STR1195## (II)-22 ##STR1196## (II)-23 ##STR1197## (II)-24 ##STR1198## (II)-25 ##STR1199## (II)-26 ##STR1200## (II)-27 ##STR1201## (II)-28 ##STR1202## (II)-29 ##STR1203## (II)-30 ##STR1204## (II)-31 ##STR1205## (II)-32 ##STR1206## (II)-33 ##STR1207## (II)-34 ##STR1208## (II)-35 ##STR1209## (II)-36 ##STR1210## (II)-37 ##STR1211## (II)-38 ##STR1212## (II)-39 ##STR1213## (II)-40 ##STR1214## (II)-41 ##STR1215## (II)-42 ##STR1216## (II)-43 ##STR1217## (II)-44 ##STR1218## (II)-45 ##STR1219## (II)-46 ##STR1220## (II)-47 ##STR1221## (II)-48 ##STR1222## (II)-49 ##STR1223## (II)-50 ##STR1224## (II)-51 ##STR1225## (II)-52 ##STR1226## (II)-53 ##STR1227## (II)-54 ##STR1228## (II)-55 ##STR1229## (II)-56 ##STR1230## (II)-57 ##STR1231## (II)-58 ##STR1232## (II)-59 ##STR1233## (II)-60 ##STR1234## (II)-61 ##STR1235## (II)-62 ##STR1236## (II)-63 ##STR1237## (II)-64 ##STR1238## (II)-65 ##STR1239## (II)-66 ##STR1240## (II)-67 ##STR1241## (II)-68 ##STR1242## (II)-69 ##STR1243## (II)-70 ##STR1244## (II)-71 ##STR1245## (II)-72 ##STR1246## (II)-73 ##STR1247## (II)-74 ##STR1248## (II)-75 ##STR1249## (II)-76 ##STR1250## (II)-77 ##STR1251## (II)-78 ##STR1252## (II)-79 ##STR1253## (II)-80 ##STR1254## (II)-81 ##STR1255## (II)-82 ##STR1256## (II)-83 ##STR1257## (II)-84 ##STR1258## (II)-85 ##STR1259## (II)-86 ##STR1260## (II)-87 ##STR1261## (II)-88 ##STR1262## (II)-89 ##STR1263## (II)-90 ##STR1264## (II)-91 ##STR1265## (II)-92 ##STR1266## (II)-93 ##STR1267## (II)-94 ##STR1268## (II)-95 ##STR1269## (II)-96 ##STR1270## (II)-97 ##STR1271## (II)-98 ##STR1272## (II)-99 ##STR1273## (II)-100 ##STR1274## (II)-101 ##STR1275## (II)-102 ##STR1276## (II)-103 ##STR1277## (II)-104 ##STR1278## (II)-105 ##STR1279## (II)-106 ##STR1280## (II)-107 ##STR1281## (II)-108 ##STR1282## (II)-109 ##STR1283## (II)-110 ##STR1284## (II)-111 ##STR1285## (II)-112 ##STR1286## (II)-113 ##STR1287## (II)-114 ##STR1288## (II)-115 ##STR1289## (II)-116 ##STR1290## (II)-117 ##STR1291## (II)-118 ##STR1292## (II)-119 ##STR1293## (II)-120 ##STR1294## (II)-121 ##STR1295## (II)-122 ##STR1296## (II)-123 ##STR1297## (II)-124 ##STR1298## (II)-125 ##STR1299## (II)-126 ##STR1300## (II)-127 ##STR1301## (II)-128 ##STR1302## (II)-129 ##STR1303## (II)-130 ##STR1304## (II)-131 ##STR1305## (II)-132 ##STR1306## (II)-133 ##STR1307## (II)-134 ##STR1308## (II)-135 ##STR1309## (II)-136 ##STR1310## (II)-137 ##STR1311## (II)-138 ##STR1312## (II)-139 ##STR1313## (II)-140 ##STR1314## (II)-141 ##STR1315## (II)-142 ##STR1316## (II)-143 ##STR1317## (II)-144 ##STR1318## (II)-145 ##STR1319## (II)-146 ##STR1320## (II)-147 ##STR1321## (II)-148 ##STR1322## (II)-149 ##STR1323## (II)-150 ##STR1324## (II)-151 ##STR1325## (II)-152 ##STR1326## (II)-153 ##STR1327## (II)-154 ##STR1328## (II)-155 ##STR1329## (II)-156 ##STR1330## (II)-157 ##STR1331## (II)-158 ##STR1332## (II)-159 ##STR1333## (II)-160 ##STR1334## (II)-161 ##STR1335## (II)-162 ##STR1336## (II)-163 ##STR1337## (II)-164 ##STR1338## (II)-165 ##STR1339## (II)-166 ##STR1340## (II)-167 ##STR1341## (II)-168 ##STR1342## (II)-169 ##STR1343## (II)-170 ##STR1344## (II)-171 ##STR1345## (II)-172 ##STR1346## (II)-173 ##STR1347## (II)-174 ##STR1348## (II)-175 ##STR1349## (II)-176 ##STR1350## (II)-177 ##STR1351## (II)-178 ##STR1352## (II)-179 ##STR1353## (II)-180 ##STR1354## (II)-181 ##STR1355## (II)-182 ##STR1356## (II)-183 ##STR1357## (II)-184 ##STR1358## (II)-185 ##STR1359## (II)-186 ##STR1360## (II)-187 ##STR1361## (II)-188 ##STR1362## (II)-189 ##STR1363## (II)-190 ##STR1364## (II)-191 ##STR1365## (II)-192 ##STR1366## (II)-193 ##STR1367## (II)-194 ##STR1368## (II)-195 ##STR1369## (II)-196 ##STR1370## (II)-197 ##STR1371## (II)-198 ##STR1372## (II)-199 ##STR1373## (II)-200 ##STR1374## (II)-201 ##STR1375## (II)-202 ##STR1376## (II)-203 ##STR1377## (II)-204 ##STR1378## (II)-205 ##STR1379## (II)-206 ##STR1380## (II)-207 ##STR1381## (II)-208 ##STR1382## (II)-209 ##STR1383## (II)-210 ##STR1384## (II)-211 ##STR1385## (II)-212 ##STR1386## (II)-213 ##STR1387## (II)-214 ##STR1388## (II)-215 ##STR1389## (II)-216 ##STR1390## (II)-217 ##STR1391## (II)-218 ##STR1392## (II)-219 ##STR1393## (II)-220 ##STR1394## (II)-221 ##STR1395## (II)-222 ##STR1396## (II)-223 ##STR1397## (II)-224__________________________________________________________________________
TABLE 38__________________________________________________________________________ ##STR1398## (III)-1 ##STR1399## (III)-2 ##STR1400## (III)-3 ##STR1401## (III)-4 ##STR1402## (III)-5 ##STR1403## (III)-6 ##STR1404## (III)-7 ##STR1405## (III)-8 ##STR1406## (III)-9 ##STR1407## (III)-10 ##STR1408## (III)-11 ##STR1409## (III)-12 ##STR1410## (III)-13 ##STR1411## (III)-14 ##STR1412## (III)-15 ##STR1413## (III)-16 ##STR1414## (III)-17 ##STR1415## (III)-18 ##STR1416## (III)-19 ##STR1417## (III)-20 ##STR1418## (III)-21 ##STR1419## (III)-22 ##STR1420## (III)-23 ##STR1421## (III)-24 ##STR1422## (III)-25 ##STR1423## (III)-26 ##STR1424## (III)-27 ##STR1425## (III)-28 ##STR1426## (III)-29 ##STR1427## (III)-30 ##STR1428## (III)-31 ##STR1429## (III)-32 ##STR1430## (III)-33 ##STR1431## (III)-34 ##STR1432## (III)-35 ##STR1433## (III)-36 ##STR1434## (III)-37 ##STR1435## (III)-38 ##STR1436## (III)-39 ##STR1437## (III)-40 ##STR1438## (III)-41 ##STR1439## (III)-42 ##STR1440## (III)-43 ##STR1441## (III)-44 ##STR1442## (III)-45 ##STR1443## (III)-46 ##STR1444## (III)-47 ##STR1445## (III)-48__________________________________________________________________________
TABLE 39______________________________________ ##STR1446## (IV)-1 ##STR1447## (IV)-2 ##STR1448## (IV)-3 ##STR1449## (IV)-4 ##STR1450## (IV)-5 ##STR1451## (IV)-6 ##STR1452## (IV)-7 ##STR1453## (IV)-8 ##STR1454## (IV)-9 ##STR1455## (IV)-10 ##STR1456## (IV)-11 ##STR1457## (IV)-12 ##STR1458## (IV)-13______________________________________
TABLE 40__________________________________________________________________________Com-poundNo. R.sup.1 R.sup.2 R.sup.3 R.sup.4__________________________________________________________________________(V)-1 H H ##STR1459## H(V)-2 CH.sub.2 CH.sub.2 NH.sub.2 CH.sub.3 H H(V)-3 ##STR1460## CH.sub.3 H(V)-4 H H H H(V)-5 CH.sub.2 CH.sub.2 NH.sub.2 CH.sub.3 H H(V)-6 ##STR1461## CH.sub.3 H H(V)-7 ##STR1462## CH.sub.3 H H(V)-8 ##STR1463## CH.sub.3 H H(V)-9 CH.sub.2 CH.sub.2 Br CH.sub.3 H H(V)-10 H H H H(V)-11 H H H H(V)-12 CH.sub.3 CH.sub.3 H CH.sub.3(V)-13 CH.sub.2 CH.sub.2 Cl CH.sub.3 H H(V)-14 ##STR1464## CH.sub.3 H H(V)-15 H H H H(V)-16 H H H H(V)-17 H H H H(V)-18 H H H H(V)-19 CH.sub.3 CH.sub.3 H H(V)-20 CH.sub.3 CH.sub.3 H H(V)-21 CH.sub.3 CH.sub.3 H H(V)-22 CH.sub.3 CH.sub.3 H ##STR1465##(V)-23 CH.sub.3 CH.sub.3 H ##STR1466##(V)-24 CH.sub.3 CH.sub.3 H ##STR1467##(V)-25 ##STR1468## CH.sub.3 H H(V)-26 ##STR1469## CH.sub.3 H H(V)-27 ##STR1470## CH.sub.3 H H(V)-28 ##STR1471## CH.sub.3 H H(V)-29 ##STR1472## CH.sub.3 H H(V)-30 ##STR1473## CH.sub.3 H H(V)-31 H H ##STR1474## H(V)-32 ##STR1475## CH.sub.3 H H(V)-33 H H H H(V)-34 H H H H(V)-35 H H H H(V)-36 H H H H(V)-37 H H H H(V)-38 CH.sub.3 CH.sub.3 H H(V)-39 H H ##STR1476## H(V)-40 H H ##STR1477## H(V)-41 OCH.sub.3 CH.sub.3 H H(V)-42 ##STR1478## CH.sub.3 H H(V)-43 ##STR1479## CH.sub.3 H H(V)-44 ##STR1480## CH.sub.3 H H(V)-45 ##STR1481## CH.sub.3 H H(V)-46 ##STR1482## CH.sub.3 H H(V)-47 ##STR1483## CH.sub.3 H H(V)-48 ##STR1484## CH.sub.3 H H(V)-49 CH.sub.3 CH.sub.3 H H(V)-50 H H H CH.sub.3(V)-51 H H ##STR1485## H(V)-52 H H H H(V)-53 H H H H(V)-54 H H H H(V)-55 H H H H(V)-56 H H H H(V)-57 H H H H(V)-58 H H H H(V)-59 H H H ##STR1486##(V)-60 CH.sub.3 CH.sub.3 H CH.sub.3(V)-61 CH.sub.3 CH.sub.3 H H(V)-62 CH.sub.3 CH.sub.3 H H(V)-63 CH.sub.3 CH.sub.3 H H(V)-64 CH.sub.3 H H H(V)-65 ##STR1487## CH.sub.3 H H(V)-66 ##STR1488## CH.sub.3 H H(V)-67 C.sub.3 H.sub.7 (n) CH.sub.3 H H(V)-68 ##STR1489## CH.sub.3 H H(V)-69 ##STR1490## CH.sub.3 H H(V)-70 ##STR1491## CH.sub.3 H H(V)-71 ##STR1492## CH.sub.3 H H(V)-72 ##STR1493## CH.sub.3 H H(V)-73 ##STR1494## CH.sub.3 H H(V)-74 CH.sub.3 CH.sub.3 CH.sub.3 H(V)-75 CH.sub.3 H H H(V)-76 H H H H(V)-77 CH.sub.3 CH.sub.3 H CH.sub.3(V)-78 ##STR1495## CH.sub.3 H H(V)-79 ##STR1496## CH.sub.3 H H(V)-80 ##STR1497## CH.sub.3 H H(V)-81 ##STR1498## CH.sub.3 H H(V)-82 ##STR1499## CH.sub.3 H H(V)-83 ##STR1500## CH.sub.3 H H(V)-84 ##STR1501## CH.sub.3 H H(V)-85 CH(OCH.sub.3).sub.2 CH.sub.3 H H(V)-86 CH(OCH.sub.3).sub.2 H H H(V)-87 CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 CH.sub.3 H H(V)-88 CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 ##STR1502## H H(V)-89 CH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2 CH.sub.3 H H(V)-90 CH.sub.3 CH.sub.3 H H(V)-91 CH.sub.3 CH.sub.3 H ##STR1503##(V)-92 C.sub.8 H.sub.17 (n) CH.sub.3 H ##STR1504##(V)-93 C.sub.8 H.sub.17 (n) CH.sub.3 H H(V)-94 CH.sub.3 CH.sub.3 H CH.sub.3(V)-95 CH.sub.3 CH.sub.3 H H(V)-96 ##STR1505## CH.sub.3 H H(V)-97 ##STR1506## C.sub.2 H.sub.5 H H(V)-98 ##STR1507## C.sub.2 H.sub.5 H H(V)-99 CHCH.sub.2 CH.sub.3 H H(V)-100 C.sub.2 H.sub.5 CH.sub.3 H H(V)-101 C.sub.2 H.sub.5 H H H(V)-102 C.sub.16 H.sub.33 (n) CH.sub.3 H H(V)-103 CH.sub.3 CH.sub.3 H H(V)-104(V)-105 ##STR1508## CH.sub.3 H H(V)-106 CH.sub.3 CH.sub.3 H H(V)-107 ##STR1509## CH.sub.3 H CH.sub.3(V)-108 CH.sub.3 CH.sub.3 H H(V)-109 ##STR1510## H ##STR1511## CH.sub.3(V)-110 CH.sub.3 CH.sub.3 H ##STR1512##(V)-111 CH.sub.3 CH.sub.3 H H(V)-112 ##STR1513## CH.sub.3 H H(V)-113 ##STR1514## CH.sub.3 H H(V)-114 CH.sub.3 CH.sub.3 H H(V)-115 CH.sub.3 CH.sub.3 H H(V)-116 CH.sub.3 CH.sub.3 H H(V)-117 CH.sub.3 CH.sub.3 H H(V)-118 ##STR1515## H H H(V)-119 OCH.sub.3 CH.sub.3 H H(V)-120 OCH.sub.3 CH.sub.3 H H(V)-121 ##STR1516## H H H(V)-122 OCH.sub.3 H H H(V)-123 CH.sub.3 CH.sub.3 H H(V)-124 ##STR1517## CH.sub.3 H H(V)-125 ##STR1518## CH.sub.3 H CH.sub.3(V)-126 ##STR1519## CH.sub.3 H H(V)-127 C.sub.5 H.sub.11 (n) CH.sub.3 H H(V)-128 ##STR1520## CH.sub.3 H H(V)-129 C.sub.13 H.sub.27 (n) CH.sub.3 H H(V)-130 ##STR1521## CH.sub.3 H H(V)-131 CH.sub.3 CH.sub.3 H H(V)-132 CH.sub.3 CH.sub.3 H CH.sub.3(V)-133 CH.sub.3 CH.sub.3 H C.sub.8 H.sub.17 (n)(V)-134 CH.sub.3 CH.sub.3 H CH.sub.3(V)-135 ##STR1522## H H H(V)-136 ##STR1523## H ##STR1524## H(V)-137 CH.sub.3 CH.sub.3 H H(V)-138 OCH.sub.3 CH.sub.3 H H(V)-139 ##STR1525## CH.sub.3 H H(V)-140 CH.sub.3 CH.sub.3 H H(V)-141 H H OC.sub.2 H.sub.5 CH.sub.3(V)-142 ##STR1526## CH.sub.3 H H(V)-143 CH.sub.3 H H ##STR1527##(V)-144 OC.sub.2 H.sub.5 CH.sub.3 H H(V)-145 CH.sub.3 CH.sub.3 H H(V)-146 OCH.sub.3 C.sub.2 H.sub.5 H H(V)-147 H H ##STR1528## OCH.sub.3(V)-148 ##STR1529## H ##STR1530## H(V)-149 ##STR1531## H C.sub.3 H.sub.7 (n) H(V)-150 ##STR1532## H OC.sub.2 H.sub.5 H(V)-151 ##STR1533## CH.sub.3 H H(V)-152 CH.sub.3 CH.sub.3 H H(V)-153 ##STR1534## CH.sub.3 H H(V)-154 ##STR1535## CH.sub.3 H H(V)-155 ##STR1536## CH.sub.3 H H(V)-156 CH.sub.3 CH.sub.3 H H(V)-157 ##STR1537## CH.sub.3 H H(V)-158 ##STR1538## CH.sub.3 H H(V)-159 CH.sub.3 CH.sub.3 H H(V)-160 CH.sub.3 CH.sub.3 H H(V)-161 CH.sub.3 CH.sub.3 H H(V)-162 CH.sub.3 CH.sub.3 H H(V)-163 H H ##STR1539## H(V)-164 CH.sub.3 CH.sub.3 H H(V)-165 C.sub.3 H.sub.7 (n) CH.sub.3 H H(V)-166 ##STR1540## CH.sub.3 H H(V)-167 CH.sub.3 CH.sub.3 H H(V)-168 C.sub.3 H.sub.7 (n) CH.sub.3 H H(V)-169 OCH.sub.3 H H CH.sub.3(V)-170 CH.sub.3 CH.sub.3 H H(V)-171 ##STR1541## H ##STR1542## H(V)-172 ##STR1543## H C.sub.3 H.sub.7 (n) H(V)-173 CH.sub.3 OCH.sub.3 H H(V)-174 CH.sub.3 H H H(V)-175 ##STR1544## CH.sub.3 H H(V)-176 ##STR1545## CH.sub.3 H H(V)-177 ##STR1546## CH.sub.3 H H(V)-178 CH.sub.3 CH.sub.3 H H(V)-179 CH.sub.3 CH.sub.3 H H(V)-180 ##STR1547## CH.sub.3 H H(V)-181 ##STR1548## CH.sub.3 H H(V)-182 CH.sub.3 CH.sub.3 H H(V)-183 ##STR1549## CH.sub.3 H H(V)-184 ##STR1550## CH.sub.3 H H(V)-185 ##STR1551## CH.sub.3 H H(V)-186 C.sub.8 H.sub.17 (n) CH.sub.3 H H(V)-187 CH.sub.3 CH.sub.3 H H(V)-188 ##STR1552## CH.sub.3 H H(V)-189 ##STR1553## CH.sub.3 H H(V)-190 ##STR1554## CH.sub.3 H H(V)-191 ##STR1555## OC.sub.2 H.sub.5 OCH.sub.3 H(V)-192 ##STR1556## OCH.sub.3 OC.sub.2 H.sub.5 H(V)-193 ##STR1557## H OC.sub.2 H.sub.5 H(V)-194 OC.sub.2 H.sub.5 H H CH.sub.3(V)-195 CH.sub.3 CH.sub.3 H H(V)-196 C.sub.2 H.sub.5 CH.sub.3 H H(V)-197 ##STR1558## CH.sub.3 H H(V)-198 ##STR1559## H H H(V)-199 ##STR1560## H H H(V)-200 ##STR1561## H CH.sub.3 H(V)-201 ##STR1562## H CH.sub.3 H(V)-202 ##STR1563## H CH.sub.3 H(V)-203 ##STR1564## H H H(V)-204 ##STR1565## H CH.sub.3 H(V)-205 ##STR1566## CH.sub.3 H H(V)-206 CH.sub.3 CH.sub.3 ##STR1567## H(V)-207 CH.sub.3 CH.sub.3 ##STR1568## H(V)-208 CH.sub.3 CH.sub.3 ##STR1569## H(V)-209 CH.sub.3 CH.sub.3 ##STR1570## H(V)-210 ##STR1571##(V)-211 ##STR1572##(V)-212 ##STR1573##(V)-213 ##STR1574##(V)-214 ##STR1575##(V)-215 ##STR1576##(V)-216 ##STR1577##(V)-217 ##STR1578##(V)-218 ##STR1579##(V)-219 ##STR1580##(V)-220 ##STR1581##(V)-221 ##STR1582##(V)-222 ##STR1583##(V)-223 ##STR1584##(V)-224 ##STR1585##(V)-225 ##STR1586##(V)-226 ##STR1587##(V)-227 ##STR1588##(V)-228 ##STR1589##(V)-229 ##STR1590##(V)-230 ##STR1591##(V)-231 ##STR1592##__________________________________________________________________________Com-poundNo. R.sup.5 R.sup.6 R.sup.7 R.sup.8__________________________________________________________________________(V)-1 H H OCH.sub.3 OCH.sub.3(V)-2 H CH.sub.3 CH.sub.3 CH.sub.3(V)-3 H H CH.sub.2 CH.sub.2 NH.sub.2 H(V)-4 H H CH.sub.2 CH.sub.2 NH.sub.2 H(V)-5 H CH.sub.3 CH.sub.3 CH.sub.3(V)-6 H CH.sub.2 CH.sub.2 NH.sub.2 CH.sub.3 CH.sub.3(V)-7 H CH.sub.3 CH.sub.2 CH.sub.2 NH.sub.2 CH.sub.3(V)-8 H CH.sub.2 CH.sub.2 NH.sub.2 CH.sub.2 CH.sub.2 NH.sub.2 CH.sub.3(V)-9 H CH.sub.3 CH.sub.3 CH.sub.3(V)-10 H ##STR1593## H H(V)-11 H H ##STR1594## H(V)-12 CH.sub.3 H ##STR1595## H(V)-13 H CH.sub.3 CH.sub.3 CH.sub.3(V)-14 H H H H(V)-15 H ##STR1596## H H(V)-16 H H ##STR1597## H(V)-17 H ##STR1598## H H(V)-18 H H ##STR1599## H(V)-19 H OCH.sub.3 OCH.sub.3 H(V)-20 H H H H(V)-21 H ##STR1600## ##STR1601## H(V)-22 H H H H(V)-23 H H C.sub.8 H.sub.17 (n) H(V)-24 H H ##STR1602## H(V)-25 H CH.sub.3 H H(V)-26 H H CH.sub.3 H(V)-27 H H H CH.sub.3(V)-28 H H CH.sub.3 H(V)-29 H CH.sub.3 H H(V)-30 H H CH.sub.3 H(V)-31 H H OCH.sub.3 OCH.sub.3(V)-32 H CH.sub.3 CH.sub.3 CH.sub.3(V)-33 H ##STR1603## H H(V)-34 H H ##STR1604## H(V)-35 H ##STR1605## H H(V)-36 H H ##STR1606## H(V)-37 H ##STR1607## H H(V)-38 H H OCH.sub.3 H(V)-39 H H OCH.sub.3 H(V)-40 H H OCH.sub.3 H(V)-41 H CH.sub.3 CH.sub.3 CH.sub.3(V)-42 H H H H(V)-43 H H H H(V)-44 H H H H(V)-45 H H H H(V)-46 H H H H(V)-47 H H H H(V)-48 H H H H(V)-49 H CH.sub.3 CH.sub.3 CH.sub.3(V)-50 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(V)-51 H H H H(V)-52 H ##STR1608## H H(V)-53 H H ##STR1609## H(V)-54 H ##STR1610## H H(V)-55 H H ##STR1611## H(V)-56 H H H ##STR1612##(V)-57 H ##STR1613## H H(V)-58 H H ##STR1614## H(V)-59 H H H H(V)-60 H H CH.sub.3 H(V)-61 H CH.sub.3 CH.sub.3 H(V)-62 H CH.sub.3 H CH.sub.3(V)-63 H H CH.sub.3 CH.sub.3(V)-64 H CH.sub.3 CH.sub.3 CH.sub.3(V)-65 H CH.sub.3 CH.sub.3 CH.sub.3(V)-66 H CH.sub.3 CH.sub.3 CH.sub.3(V)-67 H CH.sub.3 CH.sub.3 CH.sub.3(V)-68 H CH.sub.3 CH.sub.3 CH.sub.3(V)-69 H CH.sub.3 CH.sub.3 CH.sub.3(V)-70 H CH.sub.3 CH.sub.3 CH.sub.3(V)-71 H CH.sub.3 CH.sub.3 CH.sub.3(V)-72 H CH.sub.3 CH.sub.3 CH.sub.3(V)-73 H CH.sub.3 CH.sub.3 CH.sub.3(V)-74 H H H H(V)-75 H CH.sub.3 CH.sub.3 H(V)-76 H CH.sub.3 CH.sub.3 CH.sub.3(V)-77 H H ##STR1615## H(V)-78 H H CH.sub.3 CH.sub.3(V)-79 H H CH.sub.3 CH.sub.3(V)-80 H H CH.sub.3 CH.sub.3(V)-81 H CH.sub.3 H CH.sub.3(V)-82 H CH.sub.3 H CH.sub.3(V)-83 H CH.sub.3 CH.sub.3 H(V)-84 H H CH.sub.3 CH.sub.3(V)-85 H CH.sub.3 CH.sub.3 CH.sub.3(V)-86 H CH.sub.3 CH.sub.3 CH.sub.3(V)-87 H H H H(V)-88 H H H H(V)-89 H CH.sub.3 CH.sub.3 CH.sub.3(V)-90 H H C.sub.4 H.sub.9 (t) H(V)-91 H H C.sub.4 H.sub.9 (t) H(V)-92 H H C.sub.4 H.sub.9 (t) H(V)-93 H H C.sub.4 H.sub.9 (t) H(V)-94 H H C.sub.4 H.sub.9 (t) H(V)-95 H CH.sub.3 C.sub.4 H.sub.9 (t) H(V)-96 H H H H(V)-97 H CH.sub.3 CH.sub.3 CH.sub.3(V)-98 H CH.sub.3 CH.sub.3 CH.sub.3(V)-99 H CH.sub.3 CH.sub.3 CH.sub.3(V)-100 H CH.sub.3 CH.sub.3 CH.sub.3(V)-101 H CH.sub.3 CH.sub.3 CH.sub.3(V)-102 H CH.sub.3 CH.sub.3 CH.sub.3 ##STR1616## ##STR1617## H CH.sub.3 CH.sub.3(V)-105 H C.sub.4 H.sub.9 (t) C.sub.4 H.sub.9 (t) H(V)-106 H ##STR1618## CH.sub.3 CH.sub.3(V)-107 CH.sub.3 H H H(V)-108 H CH.sub.3 CH.sub.2 Cl CH.sub.3(V)-109 H H OCH.sub.3 H(V)-110 H H SC.sub.18 H.sub.37 (n) H(V)-111 H H ##STR1619## H(V)-112 H H H CH.sub.3(V)-113 H H H CH.sub.3(V)-114 H ##STR1620## CH.sub.3 CH.sub.3(V)-115 H ##STR1621## CH.sub.3 CH.sub.3(V)-116 H ##STR1622## CH.sub.3 CH.sub.3(V)-117 H ##STR1623## CH.sub.3 CH.sub.3(V)-118 H H OCH.sub.3 H(V)-119 H H H H(V)-120 H ##STR1624## ##STR1625## H(V)-121 H H OCH.sub.3 H(V)-122 H CH.sub.3 CH.sub.3 CH.sub.3(V)-123 OCH.sub.3 H H CH.sub.3(V)-124 H H SC.sub.8 H.sub.17 (n) H(V)-125 CH.sub.3 H CH.sub.3 H(V)-126 H CH.sub.3 CH.sub.3 CH.sub.3(V)-127 H CH.sub.3 CH.sub.3 CH.sub.3(V)-128 H CH.sub.3 CH.sub.3 CH.sub.3(V)-129 H CH.sub.3 CH.sub.3 CH.sub.3(V)-130 H CH.sub.3 CH.sub.3 CH.sub.3(V)-131 H H H CH.sub.3(V)-132 H H ##STR1626## H(V)-133 H CH.sub.3 H H(V)-134 H H C.sub.8 H.sub.17 (n) H(V)-135 H CH.sub.3 CH.sub.3 CH.sub.3(V)-136 H OCH.sub.3 OCH.sub.3 H(V)-137 H C.sub.4 H.sub.9 (t) H H(V)-138 H H C.sub.4 H.sub.9 (t) H(V)-139 H H C.sub.4 H.sub.9 (t) H(V)-140 H C.sub.4 H.sub.9 (t) CH.sub.3 H(V)-141 CH.sub.3 H C.sub.4 H.sub.9 (t) H(V)-142 H CH.sub.3 CH.sub.3 CH.sub.3(V)-143 H CH.sub.3 CH.sub.3 CH.sub.3(V)-144 H CH.sub.3 CH.sub.3 CH.sub.3(V)-145 H CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3(V)-146 H CH.sub.3 CH.sub.3 CH.sub.3(V)-147 H H OCH.sub.3 H(V)-148 H H OCH.sub.3 H(V)-149 H H H H(V)-150 H H H H(V)-151 H CH.sub.2 N(CH.sub.3).sub.2 CH.sub.2 N(CH.sub.3).sub.2 CH.sub.3(V)-152 H CH.sub.2 Cl CH.sub.3 CH.sub.3(V)-153 H CH.sub.3 CH.sub.3 CH.sub.3(V)-154 H C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.3(V)-155 H CH.sub.3 OCH.sub.3 OCH.sub.3(V)-156 H CH.sub.3 OCH.sub.3 OCH.sub.3(V)-157 H CH.sub.3 H ##STR1627##(V)-158 H CH.sub.3 H ##STR1628##(V)-159 H H ##STR1629## H(V)-160 H H C.sub.4 H.sub.9 (n) H(V)-161 H H H C.sub.4 H.sub.9 (n)(V)-162 H H ##STR1630## H(V)-163 H OCH.sub.3 OCH.sub.3 H(V)-164 H ##STR1631## CH.sub.3 CH.sub.3(V)-165 H ##STR1632## CH.sub.3 CH.sub.3(V)-166 H ##STR1633## CH.sub.3 CH.sub.3(V)-167 H ##STR1634## CH.sub.3 CH.sub.3(V)-168 H ##STR1635## CH.sub.3 CH.sub.3(V)-169 CH.sub.3 CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3(V)-170 H CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3(V)-171 H H H H(V)-172 H H H H(V)-173 H H CH.sub.3 CH.sub.3(V)-174 H H H H(V)-175 H CH.sub.3 CH.sub.3 CH.sub.3(V)-176 H CH.sub.3 CH.sub.3 CH.sub.3(V)-177 H CH.sub.3 CH.sub.3 CH.sub.3(V)-178 H CH.sub.3 H H(V)-179 H H CH.sub.3 H(V)-180 H CH.sub.3 ##STR1636## CH.sub.3(V)-181 H ##STR1637## CH.sub.3 CH.sub.3(V)-182 H ##STR1638## CH.sub.3 CH.sub.3(V)-183 H CH.sub.2 N(CH.sub.3).sub.2 H CH.sub.3(V)-184 H CH.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3(V)-185 H CH.sub.3 CH.sub.2 N(CH.sub.3).sub.2 CH.sub.3(V)-186 H H C.sub.4 H.sub.9 (t) H(V)-187 H CH.sub.3 H C.sub.4 H.sub.9 (t)(V)-188 H CH.sub.3 OCH.sub.3 OCH.sub.3(V)-189 H CH.sub.3 H ##STR1639##(V)-190 H CH.sub.3 OCH.sub.3 CH.sub.3(V)-191 H H H H(V)-192 H H H H(V)-193 H H H H(V)-194 CH.sub.3 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3(V)-195 H C.sub.2 H.sub.5 H H(V)-196 H ##STR1640## CH.sub.3 CH.sub.3(V)-197 H CH.sub.3 CH.sub.3 C.sub.2 H.sub.5(V)-198 H CH.sub.3 CH.sub.3 CH.sub.3(V)-199 H CH.sub.3 CH.sub.3 CH.sub.3(V)-200 H H H H(V)-201 H H H H(V)-202 H H H H(V)-203 H CH.sub.3 CH.sub.3 CH.sub.3(V)-204 H H H H(V)-205 H CH.sub.3 CH.sub.3 CH.sub.3(V)-206 H CH.sub.3 CH.sub.3 CH.sub.3(V)-207 H CH.sub.3 CH.sub.3 CH.sub.3(V)-208 H H H H(V)-209 H CH.sub.3 CH.sub.3 CH.sub.3__________________________________________________________________________
TABLE 41__________________________________________________________________________Com-poundNo. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7__________________________________________________________________________(VI)-1 OCH.sub.3 CH.sub.3 ##STR1641## H OCH.sub.3 CH.sub.3 H(VI)-2 CH(OCH.sub.3).sub.2 CH.sub.3 ##STR1642## H CH.sub.3 CH.sub.3 CH.sub.3(VI)-3 CH(OCH.sub.3).sub.2 H H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-4 CH.sub.3 CH.sub.3 H H H H H(VI)-5 ##STR1643## CH.sub.3 H H H H H(VI)-6 ##STR1644## CH.sub.3 H H H CH.sub.3 H(VI)-7 CH.sub.3 CH.sub.3 H H H OCH.sub.3 H(VI)-8 CH.sub.3 CH.sub.3 H H CH.sub.2 OCH.sub.3 CH.sub.3 CH.sub.3(VI)-9 ##STR1645## CH.sub.3 H H H H H(VI)-10 CH.sub.3 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-11 H H ##STR1646## H H H H(VI)-12 ##STR1647## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-13 H H H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-14 H H H ##STR1648## H OCH.sub.3 OCH.sub.3(VI)-15 ##STR1649## H H H H OCH.sub.3 H(VI)-16 CH.sub.3 CH.sub.3 H H OCH.sub.3 H CH.sub.3(VI)-17 ##STR1650## H H H H OCH.sub.3 H(VI)-18 H H H ##STR1651## H OCH.sub.3 H(VI)-19 ##STR1652## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-20 ##STR1653## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-21 CH.sub.3 CH.sub.3 H H H H CH.sub.3(VI)-22 ##STR1654## CH.sub.3 H H CH.sub.3 H CH.sub.3(VI)-23 ##STR1655## CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3(VI)-24 ##STR1656## CH.sub.3 H H CH.sub.3 OCH.sub.3 OCH.sub.3(VI)-25 H H H ##STR1657## H OCH.sub.3 OCH.sub.3(VI)-26 ##STR1658## CH.sub.3 H H CH.sub.3 H ##STR1659##(VI)-27 ##STR1660## OC.sub.2 H.sub.5 OCH.sub.3 H H H H(VI)-28 ##STR1661## OCH.sub.3OC.sub.2 H.sub.5 H H H H(VI)-29 ##STR1662## CH.sub.3 H H H H CH.sub.3(VI)-30 ##STR1663## H ##STR1664## H H H H(VI)-31 CH.sub.3 H H H CH.sub.3 CH.sub.3 CH.sub.3(VI)-32 ##STR1665## CH.sub.3 H H CH.sub.3 H CH.sub.3(VI)-33 ##STR1666## CH.sub.3 H H H CH.sub.3 CH.sub.3(VI)-34 CH.sub.3 CH.sub.3 H H H C.sub.4 H.sub.9 Ht)(VI)-35 ##STR1667##(VI)-36 ##STR1668##(VI)-37 ##STR1669##__________________________________________________________________________
TABLE 42 - Compound No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 (VII)-1 NH ##STR1670## CH.sub.3 H H H (VII)-2 H H H H H ##STR1671## H (VII)-3 H H H H H ##STR1672## H (VII)-4 H H H H H H H (VII)-5 CH.sub.3 CH.sub.3 H H H H H (VII)-6 ##STR1673## H CH.sub.3 CH.sub.3 H H H (VII)-7 ##STR1674## H CH.sub.3 CH.sub.3 H ##STR1675## H (VII)-8 H H H H H ##STR1676## H (VII)-9 H H H H H ##STR1677## H (VII)-10 H H H H H ##STR1678## H (VII)-11 ##STR1679## H H H H H H (VII)-12 NH ##STR1680## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-13 CH.sub.3 CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-14 H H ##STR1681## H H H H (VII)-15 H H H H H ##STR1682## H (VII)-16 H H H H H ##STR1683## H (VII)-17 H H H H H ##STR1684## H (VII)-18 CH.sub.3 CH.sub.3 H H H CH.sub.3 CH.sub.3 (VII)-19 CH.sub.3 H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-20 ##STR1685## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-21 H H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-22 NH CH.sub.3 ##STR1686## H C.sub.3 H.sub.7 (n) H (VII)-23 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 Br H H CH.sub.3 CH.sub.3 (VII)-24 ##STR1687## H C.sub.4 H.sub.9 (n) C.sub.2 H.sub.5 H C.sub.4 H.sub.9 (n) H (VII)-25 ##STR1688## H C.sub.4 H.sub.9 (n) C.sub.2 H.sub.5 H ##STR1689## H (VII)-26 ##STR1690## H C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n) H C.sub.4 H.sub.9 (n) H (VII)-27 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 H H H H H (VII)-28 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 H H H CH.sub.3 CH.sub.3 (VII)-29 CH.sub.3 H H H CH.sub.3 H H (VII)-30 CH.sub.3 H H H H CH.sub.3 H (VII)-31 H H CH.sub.3 CH.sub.3 H H H (VII)-32 ##STR1691## H CH.sub.3 CH.sub.3 H ##STR1692## H (VII)-33 ##STR1693## H CH.sub.3 H H OCH.sub.3 H (VII)-34 H H H H H CH.sub.3 H (VII)-35 ##STR1694## ##STR1695## ##STR1696## H H H (VII)-36 CH.sub.3 CH.sub.3 H H H H C.sub.4 H.sub.9 (VII)-37 ##STR1697## H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9 (t) H (VII)-38 ##STR1698## H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9 (t) H (VII)-39 OC.sub.8 H.sub.17 H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9 (t) H (VII)-40 ##STR1699## H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 H C.sub.4 H.sub.9 (t) (VII)-41 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H H H (VII)-42 ##STR1700## ##STR1701## C.sub.2 H.sub.5 H H H H (VII)-43 ##STR1702## H CH.sub.3 CH.sub.3 H H H (VII)-44 ##STR1703## H CH.sub.3 CH.sub.3 H H H (VII)-45 ##STR1704## H CH.sub.3 CH.sub.3 H H H (VII)-46 ##STR1705## H CH.sub.3 CH.sub.3 H ##STR1706## H (VII)-47 ##STR1707## H CH.sub.3 CH.sub.3 H H H (VII)-48 ##STR1708## H CH.sub.3 CH.sub.3 H H H (VII)-49 ##STR1709## H CH.sub.3 CH.sub.3 H H H (VII)-50 ##STR1710## H CH.sub.3 CH.sub.3 H H H (VII)-51 ##STR1711## H CH.sub.3 CH.sub.3 H H H (VII)-52 OCHCHCH.sub.3 H CH.sub.3 CH.sub.3 H H H (VII)-53 OCH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 H H H (VII)-54 ##STR1712## H CH.sub.3 CH.sub.3 H H H (VII)-55 ##STR1713## H CH.sub.3 CH.sub.3 H H H (VII)-56 ##STR1714## ##STR1715## H H H H H (VII)-57 ##STR1716## H CH.sub.3 H H OCH.sub.3 H (VII)-58 OCH.sub.3 H CH.sub.3 CH.sub.3 H H H (VII)-59 ##STR1717## H CH.sub.3 CH.sub.3 H OCH.sub.3 H (VII)-60 ##STR1718## H CH.sub.3 CH.sub.3 H H H (VII)-61 CH.sub.3 H ##STR1719## H H OCH.sub.3 H (VII)-62 ##STR1720## H H H H H H (VII)-63 ##STR1721## H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 (VII)-64 ##STR1722## H CH.sub.3 CH.sub.3 H CH.sub.3 H (VII)-65 ##STR1723## H CH.sub.3 CH.sub.3 H H H (VII)-66 CH.sub.3 CH.sub.3 ##STR1724## H H H H (VII)-67 ##STR1725## H CH.sub.3 CH.sub.3 H C.sub.4 H.sub.9 (t) H (VII)-68 ##STR1726## H CH.sub.3 CH.sub.3 H H H (VII)-69 ##STR1727## H CH.sub.3 CH.sub.3 H H H (VII)-70 OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H H H H (VII)-71 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 (VII)-72 ##STR1728## H CH.sub.3 H H H H (VII)-73 ##STR1729## H CH.sub.3 H H H H (VII)-74 ##STR1730## H CH.sub.3 H H H H (VII)-75 ##STR1731## H H H H H (VII)-76 OCH.sub.2 CHCH.sub.2 H CH.sub.3 CH.sub.3 H H H (VII)-77 ##STR1732## H CH.sub.3 CH.sub.3 CH.sub.3 OC.sub.4 H.sub.9 (t) H (VII)-78 OC.sub.4 H.sub.9 (n) H CH.sub.3 CH.sub.3 H H H (VII)-79 CH.sub.3 CH.sub.3 H H H OC.sub.4 H.sub.9 (t) H (VII)-80 CH.sub.3 CH.sub.3 H H H H C.sub.4 H.sub.9 (VII)-81 ##STR1733## H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9 (t) H (VII)-82 ##STR1734## H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9 (t) H (VII)-83 ##STR1735## H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9 (t) H (VII)-84 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H OC.sub.4 H.sub.9 (t) H (VII)-85 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H H C.sub.4 H.sub.9 (VII)-86 N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 H H H (VII)-87 ##STR1736## H CH.sub.3 CH.sub.3 H ##STR1737## H (VII)-88 ##STR1738## H CH.sub.3 CH.sub.3 H ##STR1739## H (VII)-89 ##STR1740## H CH.sub.3 CH.sub.3 H H ##STR1741## (VII)-90 ##STR1742## H CH.sub.3 CH.sub.3 H H H (VII)-91 OC.sub.3 H.sub.7 (iso) H CH.sub.3 CH.sub.3 H H H (VII)-92 ##STR1743## H CH.sub.3 CH.sub.3 H C.sub.3 H.sub.7 (iso) H (VII)-93 ##STR1744## H OC.sub.3 H.sub.7 (iso) H H H H (VII)-94 ##STR1745## H H H H CH.sub.3 CH.sub.3 (VII)-95 ##STR1746## H CH.sub.3 H H H ##STR1747## (VII)-96 CH.sub.3 CH.sub.3 H H CH.sub.3 H CH.sub.3 (VII)-97 H H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 (VII)-98 N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 H H H (VII)-99 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 (VII)-100 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H CH.sub.3 H (VII)-101 OC.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 H H CH.sub.3 (VII)-102 CH.sub.3 H H H H H H (VII)-103 H H H H H CH.sub.3 H (VII)-104 CH.sub.3 CH.sub.3 CH.sub.3 H H H H (VII)-105 CH.sub.3 H H H CH.sub.3 H CH.sub.3 (VII)-106 C.sub.2 H.sub.5 H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-107 CH.sub.3 H CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-108 CH.sub.3 H C.sub.2 H.sub.5 H H H H (VII)-109 ##STR1748## H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-110 ##STR1749## H CH.sub.3 H H H H (VII)-111 CH.sub.3 CH.sub.3 CH.sub.3 H H C.sub.3 H.sub.7 (n) H (VII)-112 C.sub.3 H.sub.7 H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-113 ##STR1750## H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-114 ##STR1751## H CH.sub.3 H H H H (VII)-115 ##STR1752## H CH.sub.3 H H H H (VII)-116 ##STR1753## H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-117 H H CH.sub.3 H H CH.sub.3 H (VII)-118 ##STR1754## H CH.sub.3 H H H H (VII)-119 ##STR1755## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-120 ##STR1756## H H H H OCH.sub.3 H (VII)-121 ##STR1757## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-122 ##STR1758## H H H H H H (VII)-123 ##STR1759## H H H H H H (VII)-124 H H CH.sub.3 H OCH.sub.3 H H (VII)-125 ##STR1760## H CH.sub.3 H H H H (VII)-126 ##STR1761## H H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-127 CH.sub.3 CH.sub.3 ##STR1762## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-128 ##STR1763## CH.sub.3 H H H OCH.sub.3 H (VII)-129 CH.sub.3 CH.sub.3 ##STR1764## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-130 CH.sub.3 CH.sub.3 ##STR1765## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-131 CH.sub.3 CH.sub.3 ##STR1766## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-132 ##STR1767## H CH.sub.3 H CH.sub.3 OCH.sub.3 H (VII)-133 ##STR1768## H H H CH.sub.3 OCH.sub.3 H (VII)-134 CH.sub.3 CH.sub.3 ##STR1769## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-135 CH.sub.3 CH.sub.3 ##STR1770## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-136 CH.sub.3 CH.sub.3 ##STR1771## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-137 CH.sub.3 CH.sub.3 ##STR1772## H H H H (VII)-138 CH.sub.3 CH.sub.3 ##STR1773## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-139 CH.sub.3 CH.sub.3 ##STR1774## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-140 CH.sub.3 CH.sub.3 ##STR1775## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-141 ##STR1776## H CH.sub.3 H H ##STR1777## H (VII)-142 CH.sub.3 CH.sub.3 ##STR1778## H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-143 ##STR1779## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-144 ##STR1780## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-145 ##STR1781## CH.sub.3 H H CH.sub.3 CH.sub.3 CH.sub.3 (VII)-146 ##STR1782## (VII)-147 ##STR1783##
TABLE 43__________________________________________________________________________CompoundNo. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5__________________________________________________________________________(VIII)-1 ##STR1784## H Br CH.sub.2 N(CH.sub.3).sub .2 H(VIII)-2 ##STR1785## CH.sub.3 C.sub.3 H.sub.7 (n) H Cl(VIII)-3 H H H H H(VIII)-4 ##STR1786## H H OCH.sub.3 H(VIII)-5 H H H CH.sub.3 CH.sub.3(VIII)-6 ##STR1787## H CH.sub.3 CH.sub.3 H(VIII)-7 C.sub.2 H.sub.5 H CH.sub.3 CH.sub.3 CH.sub.3(VIII)-8 ##STR1788## CH.sub.3 C.sub.3 H.sub.7 (n) H H(VIII)-9 C.sub.6 H.sub.13 (n) H H H H(VIII)-10 ##STR1789## H H OCH.sub.3 H(VIII)-11 ##STR1790## H H H H(VIII)-12 ##STR1791## CH.sub.3 H H H(VIII)-13 ##STR1792## CH.sub.3 C.sub.3 H.sub.7 (n) H H(VIII)-14 CH.sub.3 ##STR1793## H OCH.sub.3 H(VIII)-15 ##STR1794## CH.sub.3 H H H(VIII)-16 ##STR1795## CH.sub.3 C.sub.3 H.sub.7 (n) H H(VIII)-17 H CH.sub.3 H H H(VIII)-18 ##STR1796## H H H H(VIII)-19 H CH.sub.3 CH.sub.2 CHCH.sub.2 H H(VIII)-20 H CH.sub.3 C.sub.3 H.sub.7 (n) H H(VIII)-21 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3(VIII)-22 H ##STR1797## H H H(VIII)-23 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3(VIII)-24 ##STR1798## CH.sub.3 H H H(VIII)-25 ##STR1799## CH.sub.3 H H H(VIII)-26 Br ##STR1800## CH.sub.2 N(CH.sub.3).sub.2 H H(VIII)-27 ##STR1801## CH.sub.3 H H H(VIII)-28 ##STR1802## C.sub.4 H.sub.9 (n) H H H(VIII)-29 ##STR1803## C.sub.4 H.sub.9 (n) H H H(VIII)-30 ##STR1804## C.sub.2 H.sub.5 H H H(VIII)-31 CH.sub.3 CH.sub.3 H H H(VIII)-32 ##STR1805## H CH.sub.2 N(CH.sub.3).sub.2 H H(VIII)-33 H ##STR1806## CH.sub.2 N(CH.sub.3).sub.2 H H(VIII)-34 ##STR1807## ##STR1808## CH.sub.2 N(CH.sub.3).sub.2 H H(VIII)-35 ##STR1809## ##STR1810## H ##STR1811## H(VIII)-36 ##STR1812## C.sub.2 H.sub.5 H H H(VIII)-37 C.sub.2 H.sub.5 ##STR1813## H H H(VIII)-38 C.sub.2 H.sub.5 ##STR1814## H H H(VIII)-39 ##STR1815## C.sub.2 H.sub.5 H H H(VIII)-40 ##STR1816## C.sub.2 H.sub.5 H H H(VIII)-41 ##STR1817## C.sub.2 H.sub.5 H H H(VIII)-42 ##STR1818## C.sub.2 H.sub.5 H H H(VIII)-43 ##STR1819## CH.sub.3 H H H(VIII)-44 ##STR1820## H H H H(VIII)-45 CH.sub.3 ##STR1821## H H H(VIII)-46 ##STR1822## C.sub.3 H.sub.7 (n) H H H(VIII)-47 ##STR1823## ##STR1824## H OCH.sub.3 H(VIII)-48 ##STR1825## CH.sub.3 H OCH.sub.3 H(VIII)-49 ##STR1826## ##STR1827## H OCH.sub.3 H(VIII)-50 ##STR1828## H H H H(VIII)-51 ##STR1829## ##STR1830## H ##STR1831## H(VIII)-52 ##STR1832## ##STR1833## H ##STR1834## H(VIII)-53 ##STR1835## CH.sub.3 H H H(VIII)-54 ##STR1836## CH.sub.3 H H H(VIII)-55 ##STR1837## C.sub.3 H.sub.7 H H H(VIII)-56 CH.sub.3 H H H H(VIII)-57 ##STR1838## ##STR1839## H H H(VIII)-58 ##STR1840## CH.sub.3 H H H(VIII)-59 ##STR1841## CH.sub.3 H H H(VIII)-60 ##STR1842## CH.sub.3 H H H(VIII)-61 CH.sub.3 ##STR1843## H H H(VIII)-62 ##STR1844## CH.sub.3 H H H(VIII)-63 ##STR1845## CH.sub.3 H H H(VIII)-64 CH.sub.3 ##STR1846## H H H(VIII)-65 ##STR1847## CH.sub.3 H H H(VIII)-66 ##STR1848## CH.sub.3 H H H(VIII)-67 ##STR1849## CH.sub.3 H H H(VIII)-68 CHCHCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 H H H H(VIII)-69 ##STR1850## H H H H(VIII)-70 ##STR1851## ##STR1852## H ##STR1853## H(VIII)-71 ##STR1854## C.sub.3 H.sub.7 (n) H H H(VIII)-72 C.sub.3 H.sub.7 (n) ##STR1855## H H H(VIII)-73 ##STR1856## ##STR1857## H H H(VIII)-74 ##STR1858## C.sub.3 H.sub.7 (n) H H H(VIII)-75 C.sub.3 H.sub.7 (n) ##STR1859## H H H(VIII)-76 ##STR1860## C.sub.14 H.sub.29 (n) H H H(VIII)-77 ##STR1861## C.sub.3 H.sub.7 (n) H H H(VIII)-78 H CH.sub.2 CH.sub.2 NH.sub.2 (n) H H H(VIII)-79 ##STR1862## ##STR1863## CH.sub.2 N(CH.sub.3).sub.2 H H(VIII)-80 H CH.sub.3 H CH.sub.3 H(VIII)-81 ##STR1864## ##STR1865## H H H(VIII)-82 ##STR1866## ##STR1867## ##STR1868## H H(VIII)-83 ##STR1869## ##STR1870## ##STR1871## H H(VIII)-84 ##STR1872## ##STR1873## ##STR1874## H H(VIII)-85 C.sub.2 H.sub.5 H H H H(VIII)-86 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 H(VIII)-87 ##STR1875## H H H H(VIII)-88 ##STR1876## ##STR1877## ##STR1878## H H(VIII)-89 ##STR1879## ##STR1880## ##STR1881## H H(VIII)-90 ##STR1882## ##STR1883## ##STR1884## H H(VIII)-91 CH.sub.3 H H CH.sub.3 H(VIII)-92 ##STR1885## C.sub.4 H.sub.9 (Sn) H H H(VIII)-93 C.sub.2 H.sub.5 CH.sub.3 H H H(VIII)-94 C.sub.3 H.sub.7 (n) C.sub.2 H.sub.5 H H H(VIII)-95 C.sub.5 H.sub.11 (n) CH.sub.3 H H H(VIII)-96 ##STR1886## CH.sub.3 CH.sub.3 CH.sub.3(VIII)-97 H CH.sub.3 OCH.sub.3 H H(VIII)-98 ##STR1887## H H H H(VIII)-99 ##STR1888## H CH.sub.3 CH.sub.3 H(VIII)-100 ##STR1889## H H__________________________________________________________________________
TABLE 44______________________________________ ##STR1890## (IX)-1 ##STR1891## (IX)-2 ##STR1892## (IX)-3 ##STR1893## (IX)-4 ##STR1894## (IX)-5 ##STR1895## (IX)-6 ##STR1896## (IX)-7 ##STR1897## (IX)-8 ##STR1898## (IX)-9 ##STR1899## (IX)-10______________________________________
TABLE 45______________________________________ ##STR1900## (X)-1 ##STR1901## (X)-2 ##STR1902## (X)-3 ##STR1903## (X)-4 ##STR1904## (X)-5 ##STR1905## (X)-6 ##STR1906## (X)-7 ##STR1907## (X)-8 ##STR1908## (X)-9 ##STR1909## (X)-10 ##STR1910## (X)-11 ##STR1911## (X)-12 ##STR1912## (X)-13 ##STR1913## (X)-14 ##STR1914## (X)-15 ##STR1915## (X)-16 ##STR1916## (X)-17 ##STR1917## (X)-18 ##STR1918## (X)-19 ##STR1919## (X)-20 ##STR1920## (X)-21 ##STR1921## (X)-22 ##STR1922## (X)-23 ##STR1923## (X)-24 ##STR1924## (X)-25 ##STR1925## (X)-26 ##STR1926## (X)-27______________________________________
TABLE 46______________________________________ ##STR1927## (XI)-1 ##STR1928## (XI)-2 ##STR1929## (XI)-3 ##STR1930## (XI)-4 ##STR1931## (XI)-5 ##STR1932## (XI)-6 ##STR1933## (XI)-7 ##STR1934## (XI)-8 ##STR1935## (XI)-9 ##STR1936## (XI)-10 ##STR1937## (XI)-11 ##STR1938## (XI)-12 ##STR1939## (XI)-13 ##STR1940## (XI)-14 ##STR1941## (XI)-15 ##STR1942## (XI)-16 ##STR1943## (XI)-17 ##STR1944## (XI)-18 ##STR1945## (XI)-19 ##STR1946## (XI)-20 ##STR1947## (XI)-21 ##STR1948## (XI)-22 ##STR1949## (XI)-23 ##STR1950## (XI)-24 ##STR1951## (XI)-25 ##STR1952## (XI)-26 ##STR1953## (XI)-27 ##STR1954## (XI)-28 ##STR1955## (XI)-29______________________________________
TABLE 47______________________________________ ##STR1956## (XII)-1 ##STR1957## (XII)-2 ##STR1958## (XII)-3 ##STR1959## (XII)-4 ##STR1960## (XII)-5 ##STR1961## (XII)-6 ##STR1962## (XII)-7 ##STR1963## (XII)-8 ##STR1964## (XII)-9 ##STR1965## (XII)-10 ##STR1966## (XII)-11 ##STR1967## (XII)-12 ##STR1968## (XII)-13 ##STR1969## (XII)-14 ##STR1970## (XII)-15 ##STR1971## (XII)-16 ##STR1972## (XII)-17 ##STR1973## (XXI)-18 ##STR1974## (XII)-19 ##STR1975## (XII)-20 ##STR1976## (XII)-21 ##STR1977## (XII)-22 ##STR1978## (XII)-23 ##STR1979## (XII)-24 ##STR1980## (XII)-25 ##STR1981## (XII)-26 ##STR1982## (XII)-27 ##STR1983## (XII)-28 ##STR1984## (XII)-29 ##STR1985## (XII)-30 ##STR1986## (XII)-31 ##STR1987## (XII)-32 ##STR1988## (XII)-33 ##STR1989## (XII)-34 ##STR1990## (XII)-35 ##STR1991## (XII)-36 ##STR1992## (XII)-37 ##STR1993## (XII)-38 ##STR1994## (XII)-39 ##STR1995## (XII)-40 ##STR1996## (XII)-41 ##STR1997## (XII)-42 ##STR1998## (XII)-43 ##STR1999## (XII)-44 ##STR2000## (XII)-45 ##STR2001## (XII)-46 ##STR2002## (XII)-47 ##STR2003## (XII)-48 ##STR2004## (XII)-49 ##STR2005## (XII)-50 ##STR2006## (XII)-51 ##STR2007## (XII)-52 ##STR2008## (XII)-53 ##STR2009## (XII)-54 ##STR2010## (XII)-55 ##STR2011## (XII)-56 ##STR2012## (XII)-57 ##STR2013## (XII)-58 ##STR2014## (XII)-59 ##STR2015## (XII)-60 ##STR2016## (XII)-61______________________________________
FIGS. 1 to 4 are schematic cross-sectional views which show the embodiments of the electrophotographic photoconductor according to the present invention. Reference numeral 1 indicate an electroconductive support; and reference numeral 2, a single-layered photoconductive layer. Any embodiment is adoptable as long as the single-layered photoconductive layer 2 is formed on the electroconductive support 1. For instance, an undercoat layer 3 may be interposed between the electroconductive support 1 and the single-layered photoconductive layer 2 to improve the adhesion properties and the electric charge blocking characteristics, as shown in FIG. 2. In addition, a protective layer 4 may be formed on the single-layered photoconductive layer 2 to increase the mechanical durability such as the wear resistance of the photoconductor, as shown in FIG. 3. As shown in FIG. 4, both an undercoat layer 3 and a protective layer 4 may be provided.
For the electroconductive support for use in the photoconductor of the present invention, metals such as aluminum, brass, stainless steel and nickel, and alloys thereof can be employed. In addition, a thin film of electroconductive materials such as aluminum, silver, gold, nickel, indium oxide, and tin oxide may be formed on an electrically insulating support made of a material such as polyethylene terephthalate, polypropylene, nylon, glass and paper. Further, electroconductive particles such as carbon black, indium oxide and tin oxide may be dispersed in an appropriate resin, and the thus obtained resin may be provided on the above-mentioned electrically insulating support, and a sheet of may be treated to be electroconductive for the support. The shape of the electroconductive support is not limited, and a sheet-, drum- or belt-shaped support may be employed as occasion demands.
Any conventional binder resins can be employed in the single-layered photoconductive layer for use in the present invention. In particular, polymers with high electrically insulating properties and film-forming properties are preferable. For example, thermoplastic resins and thermosetting resins such as polystyrene, styrene--acrylonitrile copolymer, styrene--butadiene copolymer, styrene--maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride--vinyl acetate copolymer, polyvinyl acetate, polyvinylidene chloride, polyarylate resin, polycarbonate (bisphenol A and bisphenol Z), cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyltoluene, poly-N-vinylcarbazole, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin, phenolic resin, and alkyd resin can be employed.
To prepare the electrophotographic photoconductor of the present invention, the previously mentioned disazo pigment and trisazo pigment are mixed and simultaneously pulverized. In this case, ketones, esters, alcohols, cyclic ethers and cyclic ketones may be used as the dispersing solvents. Of these solvents, cyclic ethers and cyclic ketones are preferable, and tetrahydrofuran and cyclohexanone are in particular preferably employed as the dispersing solvents from the viewpoint of the sensitizing effect of the azo pigments. Then, the charge transporting material and the binder resin are added to the above prepared mixture of azo pigments, and the thus obtained mixture is coated on the electroconductive support by dip coating, spray coating or bead coating. Thus, an electrophotographic photoconductor according to the present invention is prepared.
It is preferable that the amount of the simultaneously pulverized mixture of the above-mentioned azo pigments be in a range of 0.01 to 10 parts by weight to 10 parts by weight of the binder resin. When the mixture of the azo pigments is contained in such an amount, the residual potential can be decreased, and the decrease of the charging characteristics and mechanical strength can be prevented.
When the charge transporting material for use in the photoconductor of the present invention is an organic positive hole transporting material, it is preferable that the amount of the charge transporting material be in a range of 1 to 15 parts by weight to 10 parts by weight of the binder resin. When the charge transporting material is contained in the photoconductive layer in the above-mentioned amount, the photosensitivity can be increased and the decrease of the charging characteristics and the mechanical strength can be prevented.
When the charge transporting material comprises an organic positive hole transporting material and an organic acceptor compound, the amount of the organic acceptor compound is preferably in a range of 1 to 15 parts by weight to 10 parts by weight of the binder resin to prevent the deterioration of the charging characteristics during the repeated operations, and the deterioration of the photosensitivity and the mechanical strength.
The thickness of the single-layered photoconductive layer is preferably in the range of 5 to 100 .mu.m, more preferably in the range of 10 to 50 .mu.m when the increase of mechanical strength and decrease of the residual potential are taken into consideration.
Other features of this invention will become apparent in the course of the following description of exemplary embodiments, which are given for illustration of the invention and are not intended to be limiting thereof.
EXAMPLE I-1
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days, and simultaneously pulverized.
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, an electrophotographic photoconductor No. I-1 according to the present invention was obtained.
The oxidation potential of the charge transporting material for use in Example I-1 was 0.50 V (vs SCE).
EXAMPLE I-2
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. I-2 according to the present invention was obtained.
EXAMPLE I-3
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.
Thus, an electrophotographic photoconductor No. I-3 according to the present invention was obtained.
EXAMPLE I-4
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a symmetrical disazo pigment of formula (1) (R.sup.2 =R.sup.2 =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. I-4 according to the present invention was obtained.
EXAMPLE I-5
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. I-5 according to the present invention was obtained.
EXAMPLE I-6
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 0.04 parts by weight.
Thus, an electrophotographic photoconductor No. I-6 according to the present invention was obtained.
EXAMPLE I-7
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 0.05 parts by weight.
Thus, an electrophotographic photoconductor No. I-7 according to the present invention was obtained.
EXAMPLE I-8
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 50 parts by weight.
Thus, an electrophotographic photoconductor No. I-8 according to the present invention was obtained.
EXAMPLE I-9
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example I-1 were separately changed to 75 parts by weight.
Thus, an electrophotographic photoconductor No. I-9 according to the present invention was obtained.
EXAMPLE I-10
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 5 parts by weight.
Thus, an electrophotographic photoconductor No. I-10 according to the present invention was obtained.
EXAMPLE I-11
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 10 parts by weight.
Thus, an electrophotographic photoconductor No. I-11 according to the present invention was obtained.
EXAMPLE I-12
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 150 parts by weight.
Thus, an electrophotographic photoconductor No. I-12 according to the present invention was obtained.
EXAMPLE I-13
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example I-1 was changed to 200 parts by weight.
Thus, an electrophotographic photoconductor No. I-13 according to the present invention was obtained.
EXAMPLE I-14
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by 1,4-dioxane.
Thus, an electrophotographic photoconductor No. I-14 according to the present invention was obtained.
EXAMPLE I-15
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by isophorone.
Thus, an electrophotographic photoconductor No. I-15 according to the present invention was obtained.
EXAMPLE I-16
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by tetrahydrofuran.
Thus, an electrophotographic photoconductor No. I-16 according to the present invention was obtained.
EXAMPLE I-17
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example I-1 was replaced by cyclohexanone.
Thus, an electrophotographic photoconductor No. I-17 according to the present invention was obtained.
COMPARATIVE EXAMPLE I-1
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1.
Ten parts by weight of the disazo pigment were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days.
The above prepared dispersion of the disazo pigment was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, a comparative electrophotographic photoconductor No. I-1 was obtained.
COMPARATIVE EXAMPLE I-2
A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Ten parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days.
The above prepared dispersion of the trisazo pigment was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, a comparative electrophotographic photoconductor No. I-2 was obtained.
COMPARATIVE EXAMPLE I-3
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were separately dispersed in a ball mill with 35 parts by weight of methyl ethyl ketone for 5 days. Then, the dispersion of the disazo pigment and the dispersion of the trisazo pigment were mixed.
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, a comparative electrophotographic photoconductor No. I-3 was obtained.
The dynamic electrostatic properties of each of the electrophotographic photoconductors No. I-1 to No. I-17 according to the present invention and the comparative electrophotographic photoconductors No. I-1 to No. I-3 were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25.degree. C. and 50% RH.
More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by white light of a halogen lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 lux. Similarly, the photoconductor was illuminated by a 780 nm-monochromatic light in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 .mu.W/cm.sup.2 after charging and dark decay.
The charging potential was expressed by a surface potential V.sub.2 (V), which was obtained two seconds after the initiation of charging; the photosensitivity was expressed by an exposure E.sub. 1/2 (lux.multidot.sec) required to reduce the surface potential obtained just before the exposure by the application of the white light to 1/2 the surface potential, and an exposure E.sub. 1/2 (.mu.J/cm.sup.2) required to reduce the surface potential obtained just before the exposure by the application of the monochromatic light to 1/2 the surface potential; and the residual potential was expressed by a surface potential V.sub.30 (V) separately obtained after the exposure for 30 seconds by use of the white light and the monochromatic light.
The results are shown in TABLE 48.
TABLE 48__________________________________________________________________________ Charge Trans- Azo porting Pigments/ Charge Material/ E.sub. 1/2 V.sub.30Disazo Trisazo Binder Trans- Binder E.sub. 1/2 V.sub.30 (mono- (mono- Solvent forCoupler Coupler Resin porting Resin V.sub.2 (white) (white) chomatic) chromatic) dispersingNo. No. Ratio Material Ratio V lux .multidot. sec V .mu.J/cm.sup.2 V pigments__________________________________________________________________________Ex. I-1 17, 24 70 1/10 * 8/10 620 0.80 35 0.35 30 Methyl ethyl ketoneEx. I-2 30 70 1/10 * 8/10 680 0.93 30 0.40 30 Methyl ethyl ketoneEx. I-3 17, 24 214 1/10 * 8/10 620 1.02 30 0.40 30 Methyl ethyl ketoneEx. I-4 17 70 1/10 * 8/10 610 0.91 35 0.41 40 Methyl ethyl ketoneEx. I-5 17, 24 3 1/10 * 8/10 650 1.31 50 0.78 120 Methyl ethyl ketoneEx. I-6 17, 24 70 0.008/10 * 8/10 660 0.85 70 0.40 80 Methyl ethyl ketoneEx. I-7 17, 24 70 0.01/10 * 8/10 630 0.81 50 0.37 40 Methyl ethyl ketoneEx. I-8 17, 24 70 10/10 * 8/10 630 0.81 10 0.36 15 Methyl ethyl ketoneEx. I-9 17, 24 70 15/10 * 8/10 500 0.83 5 0.35 5 Methyl ethyl ketoneEx. I-10 17, 24 70 1/10 * 0.5/10 680 0.90 40 0.41 35 Methyl ethyl ketoneEx. I-11 17, 24 70 1/10 * 1/10 620 0.83 35 0.35 30 Methyl ethyl ketoneEx. I-12 17, 24 70 1/10 * 15/10 620 0.80 35 0.35 30 Methyl ethyl ketoneEx. I-13 17, 24 70 1/10 * 20/10 510 0.80 30 0.31 30 Methyl ethyl ketoneEx. I-14 17, 24 70 1/10 * 8/10 530 0.70 30 0.32 35 DioxaneEx. I-15 17, 24 70 1/10 * 8/10 620 0.75 30 0.32 35 IsophoroneEx. I-16 17, 24 70 1/10 * 8/10 620 0.52 30 0.28 30 Tetrahydro- furanEx. 1-17 17, 24 70 1/10 * 8/10 610 0.50 30 0.28 30 CyclohexanoneComp. 17, 24 -- 1/10 * 8/10 610 1.10 35 3.00 40 Methyl ethylEx. I-1 ketoneComp. -- 70 1/10 * 8/10 650 0.80 35 No -- Methyl ethylEx. I-2 sensitivity ketoneComp. 17, 24 70 1/10 * 8/10 620 1.50 40 1.32 40 Methyl ethylEx. I-3 ketone__________________________________________________________________________ *4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone
EXAMPLES I-18 TO I-38
The procedure for preparation of the electrophotographic photoconductor No. I-1 in Example I-1 was repeated except that the charge transporting material, 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone, used in the photoconductive layer coating liquid in Example I-1 was replaced by the respective charge transporting materials as shown in TABLE 49.
Thus, electrophotographic photoconductors No. I-18 to No. I-38 according to the present invention were obtained.
The oxidation potential of each charge transporting material is also shown in TABLE 49.
TABLE 49______________________________________ Oxidation PotentialCharge Transporting Material [V (vs SCE)]______________________________________Ex. I-18 9-ethylcarbazole-3-aldehyde-1-methyl- 0.74 1-phenylhydrazoneEx. I-19 9-ethylcarbazole-3-aldehyde-1-benzyl- 0.81 1-phenylhydrazoneEx. I-20 2-methoxynaphthalene-1-aldehyde-1- 0.79 benzyl-1-phenylhydrazoneEx. I-21 2,2'-dimethyl-4,4'-bis(diethylamino)- 0.66 triphenylmethaneEx. I-22 9-(4-diethylaminostyryl)anthracene 0.52Ex. I-23 3-(4-ethoxystyryl)-9-ethylcarbazole 0.76Ex. I-24 4-diphenylaminostilbene 0.89Ex. I-25 4'-diphenylamino-.alpha.-phenylstilbene 0.86Ex. I-26 4'-bis(4-methylphenyl)amino-.alpha.-phenyl- 0.76 stilbeneEx. I-27 4'-(4-methoxy)diphenylamino-.alpha.-phenyl- 0.74 stilbeneEx. I-28 N,N'-diphenyl-N,N'-bis(3-methyl- 0.73 phenyl)-[1,1'-biphenyl]-4,4'-diamineEx. I-29 4'-methoxy-N,N'-bis(4-methylphenyl)- 0.76 [1,1'-biphenyl]-4-amineEx. I-30 N,N'-bis(4-methylphenyl)-[1,1'- 0.81 biphenyl]-4-amineEx. I-31 1-di(p-tolylamino)pyrene 0.81Ex. I-32 1,4-bis[4-di(p-tolyl)aminostyryl]- 0.89 benzeneEx. I-33 4,4',4"-trimethoxytriphenylamine 0.52Ex. I-34 4-methoxytriphenylamine 0.77Ex. I-35 4,4'-dimethyltriphenylamine 0.84Ex. I-36 N-ethyl-3,6-tetrabenzylaminocarbazole 0.31Ex. I-37 1-phenyl-3-(4-diethylaminostyryl)-5- 0.47 (4-diethylaminophenyl)pyrazolineEx. I-38 1,3-diphenyl-5-(4-dimethylamino- 0.67 phenyl)pyrazoline______________________________________
The dynamic electrostatic properties of each of the electrophotographic photoconductors No. I-1 and Nos. I-18 to I-38 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25.degree. C. and 50% RH.
More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by white light of a halogen lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 lux.
The charging potential was expressed by a saturated surface potential Vm (V), which was obtained in the charging time of ten seconds; and the photosensitivity was expressed by an exposure E.sub. 1/2 (lux.multidot.sec) required to reduce the surface potential obtained just before the exposure to 1/2 the surface potential. The results are shown in TABLE 50.
Further, the saturated surface potential Vm (V) was plotted as a function of the oxidation potential of the charge transporting material as shown in FIG. 5.
TABLE 50______________________________________ Vm (V) E.sub. 1/2 (lux .multidot. sec)______________________________________Example I-1 700 0.80Example I-18 1070 0.83Example I-19 1290 0.75Example I-20 1400 1.02Example I-21 1080 0.88Example I-22 950 0.89Example I-23 1330 1.10Example I-24 1380 0.70Example I-25 1300 0.72Example I-26 1210 0.66Example I-27 1190 0.64Example I-28 1210 0.55Example I-29 1150 0.73Example I-30 1270 0.75Example I-31 1200 0.67Example I-32 1530 0.73Example I-33 300 1.48Example I-34 1320 1.38Example I-35 1450 4.00Example I-36 130 1.30Example I-37 330 1.20Example I-38 1350 1.46______________________________________
To evaluate the stability of the electrostatic properties of the photoconductor, using the electrophotographic photoconductors No. I-1, No. I-20 and No. I-28 according to the present invention, the saturated surface potential Vm (V) and the exposure E.sub. 1/2 (lux.multidot.sec) were measured in the same manner as described above after fatigue of making of 5,000 copies.
The results are shown in TABLE 51.
TABLE 51______________________________________ Vm (V) after E.sub. 1/2 (lux .multidot. sec) fatigue after fatigue______________________________________Example I-1 480 1.01Example I-20 1150 0.98Example I-28 840 0.49______________________________________
As is apparent from the above results, the charging characteristics of the photoconductor are excellent when the oxidation potential of the charge transporting material for use in the photoconductor is +0.5 V (vs SCE) or more.
In addition, the electrophotographic photoconductors Nos. I-18 to I-32 employing the charge transporting materials of formulas (14), (15), (17), (19), (22), (23), (24), (28), (29), (30) and (31) show excellent charging characteristics and advantageous photosensitivity.
Furthermore, the charging stability of the electrophotographic photoconductor No. I-21 according to the present invention employing the charge transporting material of formula (17) is excellent even after the repeated operations.
COMPARATIVE EXAMPLE I-4
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of cyclohexanone for 5 days, and further diluted with 420 parts by weight of cyclohexanone. Thus, a coating liquid for a charge generation layer was obtained.
The thus obtained charge generation layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 100.degree. C. for 10 minutes, so that a charge generation layer with a thickness of 0.3 .mu.m was formed on the electroconductive support.
A mixture of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.) was dissolved in 300 parts by weight of dichloromethane. Thus, a coating liquid for a charge transport layer was obtained.
The above obtained charge transport layer coating liquid was coated on the charge generation layer by blade coating, and dried at 150.degree. C. for 20 minutes, so that a charge transport layer with a thickness of 20 .mu.m was formed on the charge generation layer.
Thus, a comparative electrophotographic photoconductor No. I-4 of laminated type was obtained.
The spectral sensitivities of the comparative photoconductor No. I-4 of laminated type and the electrophotographic photoconductor No. I-17 according to the present invention were measured by the following method: The comparative photoconductor No. I-4 and the photoconductor No. I-17 according to the present invention were respectively charged to -600 V and +600 V. The monochromatic light was taken out of the lights ranging from 900 to 400 nm by 20 nm using a commercially available monochromator, made by Nikon Corporation, and applied to each photoconductor. The exposure to reduce the surface potential just before the exposure to 1/2 the surface potential was measured as changing the wavelength of the monochromatic light used for the exposure, and the spectral sensitivities (V.multidot.cm.sup.2 /.mu.J) were calculated from the exposures. The results are shown in FIG. 6.
As is apparent from the graph in FIG. 6, the spectral sensitivity of the electrophotographic photoconductor No. I-17 according to the present invention is remarkably stable in a broad wave range from the light of a high wavelength extending to the light of a low wavelength, as compared with the comparative laminated electrophotographic photoconductor No. I-4.
EXAMPLE II-1
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of tetrahydrofuran for 5 days, and simultaneously pulverized.
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 50 parts by weight a stilbene compound serving as the organic positive hole transporting material of the following formula (a); ##STR2017## 20 parts by weight of an organic acceptor compound of the following formula (b); ##STR2018## and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, an electrophotographic photoconductor No. II-1 according to the present invention was obtained.
EXAMPLE II-2
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. II-2 according to the present invention was obtained.
EXAMPLE II-3
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.
Thus, an electrophotographic photoconductor No. II-3 according to the present invention was obtained.
EXAMPLE II-4
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a symmetrical disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. II-4 according to the present invention was obtained.
EXAMPLE II-5
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. II-5 according to the present invention was obtained.
EXAMPLE II-6
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 0.04 parts by weight.
Thus, an electrophotographic photoconductor No. II-6 according to the present invention was obtained.
EXAMPLE II-7
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 0.05 parts by weight.
Thus, an electrophotographic photoconductor No. II-7 according to the present invention was obtained.
EXAMPLE II-8
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 50 parts by weight.
Thus, an electrophotographic photoconductor No. II-8 according to the present invention was obtained.
EXAMPLE II-9
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example II-1 were separately changed to 75 parts by weight.
Thus, an electrophotographic photoconductor No. II-9 according to the present invention was obtained.
EXAMPLE II-10
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 5 parts by weight.
Thus, an electrophotographic photoconductor No. II-10 according to the present invention was obtained.
EXAMPLE II-11
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 10 parts by weight.
Thus, an electrophotographic photoconductor No. II-11 according to the present invention was obtained.
EXAMPLE II-12
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 150 parts by weight.
Thus, an electrophotographic photoconductor No. II-12 according to the present invention was obtained.
EXAMPLE II-13
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was changed to 200 parts by weight.
Thus, an electrophotographic photoconductor No. II-13 according to the present invention was obtained.
EXAMPLES II-14 TO II-27
The procedure for preparation of the electrophotographic photoconductor No. II-1 in Example II-1 was repeated except that the organic acceptor compound for use in the photoconductive layer coating liquid in Example II-1 was replaced by the respective organic acceptor compounds as shown in TABLE 52.
Thus, electrophotographic photoconductors Nos. II-14 to II-27 according to the present invention were obtained.
The dynamic electrostatic properties of each of the electrophotographic photoconductors No. II-1 to No. II-27 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25.degree. C. and 50% RH.
More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by a 780 nm-monochromatic light in such a manner that the illuminated surface of the photoconductor was 10 .mu.W/cm.sup.2.
The surface potential V.sub.s (V) which was obtained ten seconds after the initiation of charging; the surface potential V.sub.o (V) which was obtained after the dark decay; and the exposure E.sub.1/2 (.mu.J/cm.sup.2) required to reduce the surface potential V.sub.o to 1/2 the surface potential V.sub.o were measured. In addition, to evaluate the charging characteristics after the repeated electrophotographic processes, the surface potentials V.sub.s and V.sub.o, and the exposure E.sub.1/2 were measured after making of 5,000 copies.
The results are shown in TABLE 52.
TABLE 52__________________________________________________________________________ Acceptor After making 5000Disazo Trisazo Azo Pigments/ Compound/ Acceptor Initial Stage copiesCoupler Coupler Binder Resin Binder Compound V.sub.s V.sub.0 E.sub.1/2 V.sub.s V.sub.0 E.sub.1/2No. No. Ratio Resin Ratio No. (V) (V) (.mu.J/cm.sup.2) (V) (V) (.mu.J/cm.sup.2)__________________________________________________________________________Ex. II-1 17, 24 70 1/10 2/10 (b) 1530 1150 0.52 1510 1110 0.54Ex. II-2 30 70 1/10 2/10 (b) 1510 1120 0.60 1500 1080 0.60Ex. II-3 17, 24 214 1/10 2/10 (b) 1480 1090 0.55 1450 1080 0.56Ex. II-4 17 70 1/10 2/10 (b) 1500 1140 0.68 1480 1110 0.69Ex. II-5 17, 24 3 1/10 2/10 (b) 1610 1220 0.63 1590 1190 0.63Ex. II-6 17, 24 70 0.008/10 2/10 (b) 1780 1330 0.85 1760 1280 0.87Ex. II-7 17, 24 70 0.01/10 2/10 (b) 1750 1270 0.71 1710 1230 0.71Ex. II-8 17, 24 70 10/10 2/10 (b) 1300 1020 0.48 1280 990 0.48Ex. II-9 17, 24 70 15/10 2/10 (b) 1140 830 0.45 1130 810 0.45Ex. II-10 17, 24 70 1/10 0.5/10 (b) 1520 1130 0.43 1300 980 0.52Ex. II-11 17, 24 70 1/10 1/10 (b) 1490 1080 0 .47 1470 1020 0.51Ex. II-12 17, 24 70 1/10 15/10 (b) 1380 1050 0.80 1380 1040 0.80Ex. II-13 17, 24 70 1/10 20/10 (b) 1310 990 1.25 1300 990 1.23Ex. II-14 17, 24 70 1/10 2/10 (1)-18 1550 1160 0.65 1510 1120 0.60 (TABLE 17)Ex. II-15 17, 24 70 1/10 2/10 (2)-74 1490 1100 0.56 1440 1080 0.55 (TABLE 18)Ex. II-16 17, 24 70 1/10 2/10 (3)-152 1350 1070 0.53 1330 1070 0.53 (TABLE 19)Ex. II-17 17, 24 70 1/10 2/10 (4)-1 1510 1170 0.66 1470 1090 0.68 (TABLE 20)Ex. II-18 17, 24 70 1/10 2110 (5)-22 1330 1010 0.57 1310 990 0.62 (TABLE 21)Ex. II-19 17, 24 70 1/10 2/10 (6)-5 1450 1220 0.71 1410 1180 0.73 (TABLE 22)Ex. II-20 17, 24 70 1/10 2/10 (7)-10 1530 1190 0.63 1520 1170 0.69 (TABLE 23)Ex. II-21 17, 24 70 1/10 2/10 (8)-83 1490 1280 0.66 1420 1250 0.59 (TABLE 24)Ex. II-22 17, 24 70 1/10 2/10 (9)-102 1590 1230 0.51 1550 1200 0.62 (TABLE 25)Ex. II-23 17, 24 70 1/10 2/10 (10)-6 1680 1390 0.70 1650 1370 0.76 (TABLE 26)Ex. II-24 17, 24 70 1/10 2/10 (11)-2 1620 1400 0.62 1580 1330 0.66 (TABLE 27)Ex. II-25 17, 24 70 1/10 2/10 (12)-5 1610 1330 0.58 1580 1290 0.64 (TABLE 28)Ex. II-26 17, 24 70 1/10 2/10 (13)-13 1630 1370 0.61 1590 1360 0.73 (TABLE 29)Ex. II-27 17, 24 70 1/10 2/10 (14)-27 1510 1200 0.54 1480 1150 0.63 (TABLE 30)__________________________________________________________________________
As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the organic positive hole transporting material, the organic acceptor compound, and the binder resin.
EXAMPLE III-1
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of tetrahydrofuran for 5 days, and simultaneously pulverized.
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 50 parts by weight a stilbene compound serving as an organic positive hole transporting material of the following formula (a); ##STR2019## 20 parts by weight of an organic acceptor compound No. B-2 in TABLE 32, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, an electrophotographic photoconductor No. III-1 according to the present invention was obtained.
EXAMPLE III-2
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. III-2 according to the present invention was obtained.
EXAMPLE III-3
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.
Thus, an electrophotographic photoconductor No. III-3 according to the present invention was obtained.
EXAMPLE III-4
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. III-4 according to the present invention was obtained.
EXAMPLE III-5
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. III-5 according to the present invention was obtained.
EXAMPLE III-6
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 0.04 parts by weight.
Thus, an electrophotographic photoconductor No. III-6 according to the present invention was obtained.
EXAMPLE III-7
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 0.05 parts by weight.
Thus, an electrophotographic photoconductor No. III-7 according to the present invention was obtained.
EXAMPLE III-8
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 50 parts by weight.
Thus, an electrophotographic photoconductor No. III-8 according to the present invention was obtained.
EXAMPLE III-9
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example III-1 were separately changed to 75 parts by weight.
Thus, an electrophotographic photoconductor No. III-9 according to the present invention was obtained.
EXAMPLE III-10
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 5 parts by weight.
Thus, an electrophotographic photoconductor No. III-10 according to the present invention was obtained.
EXAMPLE III-11
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 10 parts by weight.
Thus, an electrophotographic photoconductor No. III-11 according to the present invention was obtained.
EXAMPLE III-12
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 150 parts by weight.
Thus, an electrophotographic photoconductor No. III-12 according to the present invention was obtained.
EXAMPLE III-13
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was changed to 200 parts by weight. Thus, an electrophotographic photoconductor No. III-13 according to the present invention was obtained.
EXAMPLES III-14 TO III-16
The procedure for preparation of the electrophotographic photoconductor No. III-1 in Example III-1 was repeated except that the organic acceptor compound for use in the photoconductive layer coating liquid in Example III-1 was replaced by the respective organic acceptor compounds as shown in TABLE 53.
Thus, electrophotographic photoconductors Nos. III-14 to III-16 according to the present invention were obtained.
TABLE 53______________________________________ Organic Acceptor Compound______________________________________Example III-14 Compound No. A-3Example III-15 Compound No. B-29Example III-16 Compound No. CIII-11______________________________________
The dynamic electrostatic properties of each of the electrophotographic photoconductors No. III-1 to No. III-16 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25.degree. C. and 50% RH.
More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by a 780 nm-monochromatic light in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 .mu.W/cm.sup.2.
The surface potential V.sub.s (V) which was obtained ten seconds after the initiation of charging; the surface potential V.sub.o (V) which was obtained after the dark decay; and the exposure E.sub.1/2 (.mu.J/cm.sup.2) required to reduce the surface potential V.sub.o to 1/2 the surface potential V.sub.o were measured. In addition, to evaluate the charging characteristics after the repeated electrophotographic processes, the surface potentials V.sub.s and V.sub.o, and the exposure E.sub.1/2 were measured after making of 5,000 copies.
The results are shown in TABLE 54.
TABLE 54__________________________________________________________________________ Acceptor After making 5000Disazo Trisazo Azo Pigments/ Compound/ Acceptor Initial Stage copiesCoupler Coupler Binder Resin Binder Compound V.sub.s V.sub.0 E.sub.1/2 V.sub.s V.sub.0 E.sub.1/2No. No. Ratio Resin Ratio No. (V) (V) (.mu.J/cm.sup.2) (V) (V) (.mu.J/cm.sup.2)__________________________________________________________________________Ex. III-1 17, 24 70 1/10 2/10 B-2 1690 1300 0.59 1660 1260 0.60Ex. III-2 30 70 1/10 2/10 B-2 1620 1280 0.62 1600 1240 0.64Ex. III-3 17, 24 214 1/10 2/10 B-2 1520 1110 0.57 1490 1120 0.58Ex. III-4 17 70 1/10 2/10 B-2 1580 1190 0.68 1520 1170 0.71Ex. III-5 17, 24 3 1/10 2/10 B-2 1730 1290 0.65 1670 1210 0.68Ex. III-6 17, 24 70 0.008/10 2/10 B-2 1810 1360 0.88 1790 1330 0.90Ex. III-7 17, 24 70 0.01/10 2/10 B-2 1770 1340 0.75 1720 1290 0.75Ex. III-8 17, 24 70 10/10 2/10 B-2 1320 1050 0.49 1290 1010 0.51Ex. III-9 17, 24 70 15/10 2/10 B-2 1180 850 0.44 1150 820 0.46Ex. III-10 17, 24 70 1/10 0.5/10 B-2 1580 1190 0.43 1340 1160 0.47Ex. III-11 17, 24 70 1/10 1/10 B-2 1540 1210 0.50 1520 1180 0.54Ex. III-12 17, 24 70 1/10 15/10 B-2 1420 1090 0.82 1410 1040 0.82Ex. III-13 17, 24 70 1/10 20/10 B-2 1380 1030 1.31 1320 990 1.30Ex. III-14 17, 24 70 1/10 2/10 A-3 1520 1180 0.60 1480 1090 0.64Ex. III-15 17, 24 70 1/10 2/10 B-23 1680 1340 0.65 1620 1290 0.71Ex. III-16 17, 24 70 1/10 2/10 CIII-11 1490 1160 0.54 1430 1110 0.55__________________________________________________________________________
As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the organic positive hole transporting material, the specified organic acceptor compound, and the binder resin.
EXAMPLE IV-1
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.1 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were dispersed in a ball mill together with 70 parts by weight of tetrahydrofuran for 5 days, and simultaneously pulverized.
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 50 parts by weight a stilbene compound serving as the organic positive hole transporting material of the following formula (a); ##STR2020## 20 parts by weight of an organic acceptor compound the following formula (c) with a reduction potential of -0.47 v (vs SCE); ##STR2021## and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, an electrophotographic photoconductor No. IV-1 according to the present invention was obtained.
EXAMPLE IV-2
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 30 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. IV-2 according to the present invention was obtained.
EXAMPLE IV-3
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 214 shown in TABLE 13.
Thus, an electrophotographic photoconductor No. IV-3 according to the present invention was obtained.
EXAMPLE IV-4
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the unsymmetrical disazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a symmetrical disazo pigment of formula (1) (R.sup.1 =R.sup.2 =hydrogen) which was prepared using the coupler No. 17 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. IV-4 according to the present invention was obtained.
EXAMPLE IV-5
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 was replaced by a trisazo pigment of formula (2) (R.sup.3 =hydrogen) which was prepared using the coupler No. 3 shown in TABLE 1.
Thus, an electrophotographic photoconductor No. IV-5 according to the present invention was obtained.
EXAMPLE IV-6
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 0.04 parts by weight.
Thus, an electrophotographic photoconductor No. IV-6 according to the present invention was obtained.
EXAMPLE IV-7
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 0.05 parts by weight.
Thus, an electrophotographic photoconductor No. IV-7 according to the present invention was obtained.
EXAMPLE IV-8
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 50 parts by weight.
Thus, an electrophotographic photoconductor No. IV-8 according to the present invention was obtained.
EXAMPLE IV-9
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the unsymmetrical disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example IV-1 were separately changed to 75 parts by weight.
Thus, an electrophotographic photoconductor No. IV-9 according to the present invention was obtained.
EXAMPLE IV-10
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 5 parts by weight.
Thus, an electrophotographic photoconductor No. IV-10 according to the present invention was obtained.
EXAMPLE IV-11
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 10 parts by weight.
Thus, an electrophotographic photoconductor No. IV-11 according to the present invention was obtained.
EXAMPLE IV-12
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 150 parts by weight.
Thus, an electrophotographic photoconductor No. IV-12 according to the present invention was obtained.
EXAMPLE IV-13
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the amount of the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was changed to 200 parts by weight.
Thus, an electrophotographic photoconductor No. IV-13 according to the present invention was obtained.
EXAMPLES IV-14 TO IV-20
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the organic acceptor compound for use in the photoconductive layer coating liquid in Example IV-1 was replaced by the respective organic acceptor compounds as shown in TABLE 55.
Thus, electrophotographic photoconductors Nos. IV-14 to IV-20 according to the present invention were obtained.
TABLE 55__________________________________________________________________________ Reduction PotentialOrganic Acceptor Compound [(V (vs SCE)]__________________________________________________________________________Ex. IV-14 ##STR2022## -0.41Ex. IV-15 ##STR2023## -0.59Ex. IV-16 ##STR2024## -0.87Ex. IV-17 ##STR2025## -0.92Ex. IV-18 ##STR2026## -1.06Ex. IV-19 ##STR2027## -0.15Ex. IV-20 ##STR2028## -1.42__________________________________________________________________________
COMPARATIVE EXAMPLE IV-1
An unsymmetrical disazo pigment of formula (1) in which R.sup.1 and R.sup.2 are hydrogen was prepared using the couplers No. 17 and No. 24 shown in TABLE 1. A trisazo pigment of formula (2) in which R.sup.3 is hydrogen was prepared using the coupler No. 70 shown in TABLE 2.
Five parts by weight of the disazo pigment and 5 parts by weight of the trisazo pigment were separately dispersed in a ball mill with 35 parts by weight of tetrahydrofuran for 5 days. Then, the dispersion of the disazo pigment and the dispersion of the trisazo pigment were mixed.
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of the same organic positive hole transporting material as used in Example IV-1, 20 parts by weight of the same organic acceptor compound as used in Example IV-1, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, a comparative electrophotographic photoconductor No. IV-1 was obtained.
COMPARATIVE EXAMPLE IV-2
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the trisazo pigment of formula (2) prepared by use of the coupler No. 70 was not employed in the preparation of the photoconductive layer coating liquid.
Thus, a comparative electrophotographic photoconductor No. IV-2 was obtained.
COMPARATIVE EXAMPLE IV-3
The procedure for preparation of the electrophotographic photoconductor No. IV-1 in Example IV-1 was repeated except that the unsymmetrical disazo pigment of formula (1) prepared by use of the couplers Nos. 17 and 24 was not employed in the preparation of the photoconductive layer coating liquid.
Thus, a comparative electrophotographic photoconductor No. IV-3 was obtained.
The dynamic electrostatic properties and the charging characteristics after the repeated electrophotographic processes of each of the electrophotographic photoconductors No. IV-1 to No. IV-20 according to the present invention and the comparative electrophotographic photoconductors No. IV-1 to No. IV-3 were measured in the same manner as in Example II-1.
The results are shown in TABLE 56.
TABLE 56__________________________________________________________________________ Acceptor After making 5000Disazo Trisazo Azo Pigments/ Compound/ Initial Stage copiesCoupler Coupler Binder Resin Binder V.sub.s V.sub.0 E.sub. 1/2 V.sub.s V.sub.0 E.sub. 1/2No. No. Ratio Resin Ratio (V) (V) (.mu.J/cm.sup.2) (V) (V) (.mu.J/cm.sup.2)__________________________________________________________________________Ex. IV-1 17, 24 70 1/10 2110 1510 1140 0.49 1490 1100 0.51Ex. IV-2 30 70 1/10 2/10 1470 1100 0.56 1450 1070 0.56Ex. IV-3 17, 24 214 1/10 2/10 1450 1080 0.53 1410 1060 0.54Ex. IV-4 17 70 1/10 2/10 1480 1120 0.65 1440 1090 0.67Ex. IV-5 17, 24 3 1/10 2/10 1580 1240 0.60 1550 1200 0.59Ex. IV-6 17, 24 70 0.008/10 2/10 1690 1300 0.80 1660 1240 0.82Ex. IV-7 17, 24 70 0.01/10 2/10 1660 1230 0.69 1650 1190 0.71Ex. IV-8 17, 24 70 10/10 2/10 1290 1000 0.45 1250 970 0.45Ex. IV-9 17, 24 70 15/10 2/10 1110 820 0.42 1090 800 0.42Ex. IV-10 17, 24 70 1/10 0.5/10 1490 1090 0.43 1020 830 0.40Ex. IV-11 17, 24 70 1/10 1/10 1460 1050 0.44 1450 1040 0.46Ex. IV-12 17, 24 70 1/10 15/10 1360 1020 0.76 1340 1000 0.75Ex. IV-13 17, 24 70 1/10 20/10 1280 970 1.22 1210 920 1.24Ex. IV-14 17, 24 70 1/10 2/10 1530 1250 0.55 1500 1210 0.56Ex. IV-15 17, 24 70 1/10 2/10 1460 1270 0.50 1460 1260 0.51Ex. IV-16 17, 24 70 1/10 2/10 1350 1100 0.66 1320 1070 0.68Ex. IV-17 17, 24 70 1/10 2/10 1620 1490 0.71 1620 1480 0.73Ex. IV-18 17, 24 70 1/10 2/10 1390 1100 0.64 1360 1070 0.65Comp. 17, 24 70 1/10 2/10 1400 1090 3.55 1350 1050 3.72Ex. IV-1Comp. 17, 24 None 1/10 2/10 1560 1330 No 1550 1320 NoEx. IV-2 sensi- sensi- tivity tivityComp. None 70 1/10 2/10 1530 1370 2.29 1500 1330 2.60Ex. IV-3Ex. IV-19 17, 24 70 1/10 2/10 1490 1170 1.85 1460 1160 1.84Ex. IV-20 17, 24 70 1/10 2/10 1620 1390 3.14 820 510 3.95__________________________________________________________________________
As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the organic positive hole transporting material, the organic acceptor compound having a reduction potential in a range of -0.2 to -1.2 V (vs SCE), and the binder resin.
EXAMPLE V-1
Five parts by weight of a disazo pigment of formula (d) and 5 parts by weight of a trisazo pigment of formula (e) were dispersed in a ball mill together with 70 parts by weight of methyl ethyl ketone for 5 days, and simultaneously pulverized. ##STR2029##
The above prepared mixture was added to a solution consisting of 100 parts by weight of Z type polycarbonate with a molecular weight of 60,000, 300 parts by weight of tetrahydrofuran, 80 parts by weight of 4-diethylaminobenzaldehyde-1-benzyl-1-phenylhydrazone serving as the charge transporting material, 5 parts by weight of a commercially available hindered amine compound (Trademark "Sanol LS-770", made by Sankyo Company, Limited) serving as the antioxidant, and 0.1 parts by weight of a commercially available silicone oil (Trademark "KF-50", made by Shin-Etsu Chemical Co., Ltd.). Thus, a coating liquid for a photoconductive layer was obtained.
The thus obtained photoconductive layer coating liquid was coated on an aluminum plate (Trademark "A1080", made by Sumitomo Light Metal Industries, Ltd.) with a thickness of 0.2 mm by blade coating, dried at 150.degree. C. for 20 minutes, so that a photoconductive layer with a thickness of 20 .mu.m was formed on the electroconductive support.
Thus, an electrophotographic photoconductor No. V-1 according to the present invention was obtained.
EXAMPLE V-2
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the disazo pigment of formula (d) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a disazo pigment of the following formula (f): ##STR2030##
Thus, an electrophotographic photoconductor No. V-2 according to the present invention was obtained.
EXAMPLE V-3
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the trisazo pigment of formula (e) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a trisazo pigment of the following formula (g): ##STR2031##
Thus, an electrophotographic photoconductor No. V-3 according to the present invention was obtained.
EXAMPLE V-4
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the disazo pigment of formula (d) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a disazo pigment of the following formula (h): ##STR2032##
Thus, an electrophotographic photoconductor No. V-4 according to the present invention was obtained.
EXAMPLE V-5
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the trisazo pigment of formula (e) for use in the photoconductive layer coating liquid in Example V-1 was replaced by a trisazo pigment of the following formula (i): ##STR2033##
Thus, an electrophotographic photoconductor No. V-5 according to the present invention was obtained.
EXAMPLE V-6
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 0.04 parts by weight.
Thus, an electrophotographic photoconductor No. V-6 according to the present invention was obtained.
EXAMPLE V-7
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 0.05 parts by weight.
Thus, an electrophotographic photoconductor No. V-7 according to the present invention was obtained.
EXAMPLE V-8
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 50 parts by weight.
Thus, an electrophotographic photoconductor No. V-8 according to the present invention was obtained.
EXAMPLE V-9
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the disazo pigment and that of the trisazo pigment for use in the photoconductive layer coating liquid in Example V-1 were separately changed to 75 parts by weight.
Thus, an electrophotographic photoconductor No. V-9 according to the present invention was obtained.
EXAMPLE V-10
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 5 parts by weight.
Thus, an electrophotographic photoconductor No. V-10 according to the present invention was obtained.
EXAMPLE V-11
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 10 parts by weight.
Thus, an electrophotographic photoconductor No. V-11 according to the present invention was obtained.
EXAMPLE V-12
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 150 parts by weight.
Thus, an electrophotographic photoconductor No. V-12 according to the present invention was obtained.
EXAMPLE V-13
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the amount of the charge transporting material for use in the photoconductive layer coating liquid in Example V-1 was changed to 200 parts by weight.
Thus, an electrophotographic photoconductor No. V-13 according to the present invention was obtained.
EXAMPLE V-14
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by 1,4-dioxane.
Thus, an electrophotographic photoconductor No. V-14 according to the present invention was obtained.
EXAMPLE V-15
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by isophorone.
Thus, an electrophotographic photoconductor No. V-15 according to the present invention was obtained.
EXAMPLE V-16
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by tetrahydrofuran.
Thus, an electrophotographic photoconductor No. V-16 according to the present invention was obtained.
EXAMPLE V-17
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that methyl ethyl ketone used in dispersing the azo pigments in Example V-1 was replaced by cyclohexanone.
Thus, an electrophotographic photoconductor No. V-17 according to the present invention was obtained.
The dynamic electrostatic properties of each of the electrophotographic photoconductors No. V-1 to No. V-17 according to the present invention were measured in the same manner as in Example I-1.
The results are shown in TABLE 57.
TABLE 57__________________________________________________________________________ Charge Transporting V.sub.30 E.sub.1/2 Azo Pigments/ Material/ Solvent for E.sub.1/2 (mono- (mono-Disazo Trisazo Binder Resin Binder Resin dispersing V.sub.2 (white) chromatic) chromatic) V.sub.30Coupler No. Coupler No. Ratio Ratio pigments V lux .multidot. sec V .mu.J/cm.sup.2 V__________________________________________________________________________Ex. V-1 Formula (d) Formula (e) 1/10 8/10 MEK 720 1.00 45 0.50 40Ex. V-2 Formula (f) Formula (e) 1/10 8/10 MEK 740 1.12 40 0.60 40Ex. V-3 Formula (d) Formula (g) 1/10 8/10 MEK 710 1.18 45 0.62 45Ex. V-4 Formula (h) Formula (e) 1/10 8/10 MEK 690 1.08 45 0.65 45Ex. V-5 Formula (d) Formula (i) 1/10 8/10 MEK 720 1.40 60 0.88 55Ex. V-6 Formula (d) Formula (e) 0.008/10 8/10 MEK 770 1.15 85 0.62 75Ex. V-7 Formula (d) Formula (e) 0.01/10 8/10 MEK 750 1.10 75 0.55 60Ex. V-8 Formula (d) Formula (e) 10/10 8/10 MEK 690 0.97 25 0.47 30Ex. V-9 Formula (d) Formula (e) 15/10 8/10 MEK 580 0.97 15 0.46 25Ex. V-10 Formula (d) Formula (e) 1/10 0.5/10 MEK 760 1.12 50 0.62 50Ex. V-11 Formula (d) Formula (e) 1/10 1/10 MEK 735 1.08 45 0.58 45Ex. V-12 Formula (d) Formula (e) 1/10 15/10 MEK 700 0.98 40 0.48 35Ex. V-13 Formula (d) Formula (e) 1/10 20/10 MEK 635 0.99 40 0.48 30Ex. V-14 Formula (d) Formula (e) 1/10 8/10 Dioxane 650 0.95 40 0.47 40Ex. V-15 Formula (d) Formula (e) 1/10 8/10 Isophorone 720 0.98 40 0.46 40Ex. V-16 Formula (d) Formula (e) 1/10 8/10 THF 715 0.89 35 0.42 35Ex. V-17 Formula (d) Formula (e) 1/10 8/10 Anone 700 0.87 35 0.40 30__________________________________________________________________________ MEK: Methyl Ethyl Ketone, THF: Tetrahydrofuran, Anone: Cyclohexanone
EXAMPLE V-18 TO V-38
The procedure for preparation of the electrophotographic photoconductor No. V-1 in Example V-1 was repeated except that the antioxidant used in the photoconductive layer coating liquid in Example V-1 was replaced by the respective antioxidants as shown in TABLE 58.
Thus, electrophotographic photoconductors No. V-18 to No. V-38 according to the present invention were obtained.
TABLE 58______________________________________Example No. Antioxidant______________________________________Ex. V-18 3,5-di-t-butyl-4-hydroxytoluene (made by Tokyo Kasei Kogyo Co., Ltd.)Ex. V-19 Trademark "SUMILIZER MDP-S", made by Sumitomo Chemical Co., Ltd.Ex. V-20 Trademark "SUMILIZER TPM", made by Sumitomo Chemical Co., Ltd.Ex. V-21 Trademark "SANOL LS-2626", made by Sankyo Company, LimitedEx. V-22 Trademark "MARK PEP-24", made by Asahi Denka Kogyo K.K.Ex. V-23 Trademark "IRGANOX-1330", made by CIBA- GEIGY, Ltd.Ex. V-24 Compound No. (I)-13Ex. V-25 Compound No. (II)-2Ex. V-26 Compound No. (III)-1Ex. V-27 Compound No. (III)-20Ex. V-28 Compound No. (V)-49Ex. V-29 Compound No. (V)-72Ex. V-30 Compound No. (VI)-6Ex. V-31 Compound No. (VII)-18Ex. V-32 Compound No. (VIII)-23Ex. V-33 Compound No. (IX)-1Ex. V-34 Compound No. (X)-6Ex. V-35 Compound No. (X)-21Ex. V-36 Compound No. (XI)-2Ex. V-37 Compound No. (XI)-20Ex. V-38 Compound No. (XII)-4______________________________________
EXAMPLE V-39
The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 0.05 parts by weight.
Thus, an electrophotographic photoconductor No. V-39 according to the present invention was obtained.
EXAMPLE V-40
The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 0.1 parts by weight.
Thus, an electrophotographic photoconductor No. V-40 according to the present invention was obtained.
EXAMPLE V-41
The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 20 parts by weight.
Thus, an electrophotographic photoconductor No. V-41 according to the present invention was obtained.
EXAMPLE V-42
The procedure for preparation of the electrophotographic photoconductor No. V-25 in Example V-25 was repeated except that the amount of the antioxidant (Compound No. II-2 in TABLE 37) used in the photoconductive layer coating liquid in Example V-25 was changed from 5 parts by weight to 30 parts by weight.
Thus, an electrophotographic photoconductor No. V-42 according to the present invention was obtained.
The dynamic electrostatic properties of each of the electrophotographic photoconductors No. V-1 and Nos. V-18 to V-42 according to the present invention were measured by using a commercially available test apparatus (Trademark "EPA-8100", made by Kawaguchi Electro Works Co., Ltd.) under the circumstances of 25.degree. C. and 50% RH.
More specifically, each photoconductor was charged positively in the dark under application of +6 kV for 10 seconds. Then, each photoconductor was allowed to stand in the dark for 20 seconds without applying any charge thereto. After that, the photoconductor was illuminated by white light of a halogen lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 10 lux.
The charging potential was expressed by a saturated surface potential Vm (V), which was obtained in the charging time of ten seconds; the photosensitivity was expressed by an exposure E.sub.1/2 (lux.multidot.sec) required to reduce the surface potential obtained just before the exposure to 1/2 the surface potential; and the residual potential was expressed by a surface potential V.sub.30 (V) obtained 30 seconds after the exposure.
In addition, to evaluate the stability of the electrostatic properties of the photoconductor, the saturated surface potential Vm' (V), the exposure E.sub.1/2' (lux.multidot.sec), and the surface potential V.sub.30' were measured in the same manner as described above after fatigue of making of 5,000 copies.
The results are shown in TABLE 59.
TABLE 59______________________________________Before fatigue After fatigueVm E.sub.1/2 V30' Vm' E.sub.1/2 ' V30'(V) (lux .multidot. sec) (V) (V) (lux .multidot. sec) (V)______________________________________Ex. V-1 980 1.00 45 820 1.35 85Ex. V-18 720 0.82 35 550 0.98 40Ex. V-19 730 0.85 40 580 0.93 50Ex. V-20 725 0.80 45 585 0.92 50Ex. V-21 710 0.82 45 560 0.95 55Ex. V-22 700 0.81 35 545 0.97 40Ex. V-23 705 0.86 45 550 0.98 50Ex. V-24 950 0.81 40 850 0.83 55Ex. V-25 1050 0.82 40 970 0.84 60Ex. V-26 1010 0.81 40 950 0.84 55Ex. V-27 990 0.85 40 900 0.93 55Ex. V-28 920 0.83 45 830 0.87 65Ex. V-29 950 0.84 40 800 0.90 60Ex. V-30 940 0.82 40 830 0.87 55Ex. V-31 945 0.84 40 825 0.90 60Ex. V-32 960 0.83 40 850 0.90 55Ex. V-33 955 0.82 40 840 0.88 55Ex. V-34 940 0.85 40 810 0.90 55Ex. V-35 935 0.86 40 800 0.94 55Ex. V-36 955 0.88 45 815 0.97 65Ex. V-37 940 0.90 45 795 0.98 70Ex. V-38 1000 0.84 40 830 0.88 60Ex. V-39 920 0.80 35 590 0.92 40Ex. V-40 990 0.81 40 830 0.83 50Ex. V-41 1180 0.90 60 1120 1.25 80Ex. V-42 1250 1.02 85 1180 1.55 120______________________________________
As is apparent from the results shown in TABLE 59, the charging characteristics of the photoconductor are remarkably improved when the single-layered photoconductive layer comprises an antioxidant. In particular, the charging characteristics are excellent and the photosensitivity and residual potential are advantageous in Examples V-24 to V-38 in which antioxidants of formulas (I) to (XII) are employed, and in Examples V-40 and V-41 in which the amount of the antioxidant contained in the photoconductive layer is preferable.
As previously explained, the electrophotographic photoconductors according to the present invention exhibit high photosensitivity in a broad wave range from the visible region extending to the near infrared region, and excellent charging stability when the single-layered photoconductive layer comprises a simultaneously pulverized mixture comprising the disazo pigment of formula (1) and the trisazo pigment of formula (2), the charge transporting material, the binder resin and the antioxidant. In this case, the decrease of image density and the toner deposition on the background can be prevented.
Japanese Patent Application 5-280543 filed on Oct. 14, 1993; Japanese Patent Application 5-354296 filed on Dec. 30, 1993; Japanese Patent Application 5-354295 filed on Dec. 30, 1993; Japanese Patent Application 5-341779 filed on Dec. 11, 1993; and Japanese Patent Application 6-193563 filed on Jul. 26, 1994 are hereby incorporated by reference.

Number	Date	Country
5-280543	Oct 1993	JPX
5-341779	Dec 1993	JPX
5-354295	Dec 1993	JPX
5-354296	Dec 1993	JPX
6-193563	Jul 1994	JPX

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5350653	Shoshi et al.	Sep 1994

Electrophotographic photoconductor containing disazo and trisazo pigments

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