Bisstyryl compound and the electrophotographic photoreceptors relating thereto

FIELD OF THE INVENTION
This invention relates to a bisstyryl compound and the electrophotographic photoreceptors relating thereto and, particularly, to the bisstyryl compound suitable for a carrier transporting material in an electrophotographic photoreceptor comprising a photoreceptive layer containing a carrier generating material and the carrier transporting material.
BACKGROUND OF THE INVENTION
As for an electrophotographic photoreceptor, those containing each an inorganic photoconductor such as selenium, zinc oxide, cadmium sulfide and silicon as the principal component have heretofore been widely known. However, their characteristics such as the thermal stability and durability thereof have not always been satisfactory and they have also had the problems of manufacture and handling.
On the other hand, the photoreceptors comprising each a photoreceptive layer containing an organic photoconductive compound as the principal component thereof are relatively easier for manufacture, inexpensive in cost, easier for handling and, generally, excellent in thermal stability as compared to a selenium photoreceptor. As for the organic photoconductive compounds, a poly-N-vinylcarbazole has been well-known. There have already been put to practical use the photoreceptors comprising each a photoreceptive layer containing an electric-charge transfer complex produced of the above-mentioned poly-N-vinylcarbazole and a Lewis acid such as 2,4,7-trinitro-9-fluorenone as the principal component thereof.
Further, on the other hand, there have also been known a photoreceptor comprising a laminated or single layered function-separated type photoreceptive layer in which the carrier generating function and carrier transporting function of the photoconductor thereof can be performed by separate materials, respectively. For example, there have already been put to practical use the photoreceptors comprising each a photoreceptive layer comprising a carrier generating layer formed of a thin amorphous selenium layer and a carrier transporting layer containing a poly-N-vinylcarbazole as the principal component thereof.
However, the above-mentioned poly-N-vinylcarbazole lacks a flexibility and the coated layer thereof is solid and fragile and is liable to be cracked or peeled off. Every photoreceptor applied therewith is, therefore, deteriorated in durability. When the above-mentioned defects are improved by adding a plasticizer, the residual potentials are increased in an electrophotographic process and are accumulated as in making repetition use so as to produce fogs increasingly, so that a copied image is spoiled.
A low-molecular organic photoconductive compound has generally no coated-layer forming function. Therefore, when the compound is used with a suitable binder in combination and the kinds and composite proportions of the binders are suitably selected, the compound is preferable from the viewpoint that the physical properties of the coated layer or the photoreceptive characteristics can each be controlled to some extent. However, there are some limitation to the kinds of the organic photoconductive compounds each having a relatively high compatibility with the binders. Actually, there are limited to the kinds of the binders applicable to form the photoreceptive layers of an electrophotographic photoreceptor.
For example, 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole described in U.S. Pat. No. 3,189,447 is low in compatibility with the binders commonly applicable as a material of the photoreceptive layers of an electrophotographic photoreceptor, such as a polyester and a polycarbonate. In other words, when a photoreceptive layer is formed by mixing them up in a proportion required for controlling the electrophotographic characteristics, the crystals of oxadiazole are deposited at a temperature of not lower than 50.degree. C., so as to have a defect that the electrophotographic characteristics such as electric-charge coercive force and photoreceptivity deteriorate.
In the meanwhile, each of the diaryl alkane derivatives described in U.S. Pat. No. 3,820,989 has few problems of the compatibility with a binder. However, it is low in stability against light. When it is applied to a repetition-transfer type electrophotographic photoreceptor to which an electric-charge.multidot.an exposure are applied repeatedly, it has a defect that the photoreceptivity of the photoreceptive layer is gradually lowered.
In U.S. Pat. No. 3,274,000 and Japanese Patent Examined Publication No. 47-36428/1972, the different types of phenothiazine derivatives are described, respectively. However, every one of them has the defect that the photoreceptivities thereof are low and the stabilities thereof are also low in repetition use.
The stilbene compounds described in Japanese Patent Publication Open to Public Inspection (hereinafter referred to as JP OPI Publication) Nos. 58-65440/1983, 58-190953/1983 and 63-149652/1988 are each relatively excellent in electric-charge coercive force and photoreceptivity. However, they are still not satisfactory in durability in repetition use.
In the meanwhile, the photoreceptors capable of solving the above-mentioned defects include those applied with a distilbene compound as the carrier transporting material thereof, such as those described in JP OPI Publication Nos. 60-175052/1985, 60-174749/1985, 62-120346/1987, 64-32265/1989, 1-106069/1989, 1-93746/1989 and 1-274154/1989. However, they can still not be satisfactory in durability when they are incorporated into a copier or a printer and are used repeatedly.
Particularly, there have been the following for problems.
1) In a high-speed copier having a high linear velocity, a cycle of electric-charging.multidot.exposure.multidot.electric neutralization is shortened. Therefore, the residual potential is seriously raised in repetition copying operations;
2) When making use of a copier for repeating copying operations, a small white spotted image defect (that is so-called a white-dot) is produced in solid-black image areas;
3) When making use of a reversal development type printer, there found the defects that an exposure potential (VL) is raised at a low temperature and an electric-charge potential (VH) is lowered in repetition use; and
4) A small black-spotted image defect (that is so-called a black-dot) is liable to be produced in white image areas.
As described above, there has not been found any carrier transporting material having the characteristics which can be practical and satisfactory for providing an electrophotographic photoreceptor.
SUMMARY OF THE INVENTION
It is an object of the invention to provide a compound suitable for a carrier transporting material for a highly photoreceptive and highly durable photoreceptor applicable to a copier or printer and the electrophotographic photoreceptors relating thereto.
The other objects of the invention are to provide the following (1) through (4);
(1) a compound suitable for a carrier generating material for a photoreceptor not raising any residual potential thereof even when repeating a series of electric-charging.multidot.exposure.multidot.electric neutralization operations, in a high-speed copier having a high linear velocity, and the electrophotographic photoreceptors relating thereto;
(2) a compound suitable for a carrier transporting material for a photoreceptor not producing any small white-spotted image defect (that is so-called a white-dot) in the solid-black image areas even in repetition use, when the photoreceptor is incorporated into a copier, and the electrophotographic photoreceptors relating thereto;
(3) a compound suitable for a carrier generating material for a photoreceptor neither raising an exposure potential (VL) at a low temperature even in repetition use, nor lowering an electric-charge potential (VH) even in repetition use, in the case where the photoreceptor is incorporated into a reversal development type printer, and the electrophotographic photoreceptors relating thereto; and
(4) a compound suitable for a carrier transporting material for a photoreceptor not producing any small black-spotted image defect (that is so-called a black-dot) in the white image areas, and the electrophotographic photoreceptors relating thereto.

BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is the IR spectra of an example of the carrier transporting materials relating to the invention;
FIG. 2 is the IR spectra of another example of the carrier transporting materials relating to the invention;
FIG. 3 is the IR spectra of a further example of the carrier transporting materials relating to the invention;
FIG. 4 is the IR spectra of a still further example of the carrier transporting materials relating to the invention;
FIG. 5 is the IR spectra of a yet another example of the carrier transporting materials relating to the invention;
FIG. 6 is the cross-sectional view of an example of the electrophotographic photoreceptors relating to the invention;
FIG. 7 is the cross-sectional view of another example of the electrophotographic photoreceptors relating to the invention;
FIG. 8 is the cross-sectional view of a further example of the electrophotographic photoreceptors relating to the invention;
FIG. 9 is the cross-sectional view of a still further example of the electrophotographic photoreceptors relating to the invention;
FIG. 10 is the cross-sectional view of a yet another example of the electrophotographic photoreceptors relating to the invention;
FIG. 11 is the cross-sectional view of another example of the electrophotographic photoreceptors relating to the invention;
Wherein, reference numeral
1: a support
2: a carrier generating layer
3: a carrier transporting layer
5: an interlayer
6: a layer containing a carrier generating material and a carrier transporting material

DETAILED DESCRIPTION OF THE INVENTION
This invention relates to the bisstyryl compounds represented by the following Formula [I] and to the electrophotographic photoreceptors each containing the above-mentioned bisstyryl compound. ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Ar.sup.1 and Ar.sup.2 represent each ##STR3## wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22 and R.sup.23 represent each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, a halogen atom, ##STR4## wherein R.sup.24 and R.sup.25 represent each an alkyl group, an aralkyl group or a phenyl group, --OR.sup.26 wherein R.sup.26 represents an alkyl group, an aralkyl group or a phenyl group, a hydroxyl group, an aralkyl group, a phenyl group, --R.sup.27 COOR.sup.28 wherein R.sup.27 represents an alkylene group and R.sup.28 represents an alkyl group, --COOR.sup.29 wherein R.sup.29 represents an alkyl group, --R.sup.30 OCOR.sup.31 wherein R.sup.30 represents an alkylene group and R.sup.31 represents an alkyl group, or --OCOR.sup.32 wherein R.sup.32 represents an alkyl group; provided, Ar.sup.1 and Ar.sup.2 shall not represent each ##STR5## (non-substituted) at the same time, and when Ar.sup.1 represents ##STR6## (wherein R and R' represents each an alkyl group having 1 to 4 carbon atoms), n is 1, m is 1 or 0. Regarding Ar.sup.1 and Ar.sup.2, a preferred combination is that Ar.sup.1 represents a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms and Ar.sup.2 represents a non-substituted phenyl group. More preferably, Ar.sup.1 is a substituted with a methyl group, and most preferably is a para-methyl group. ##STR7## wherein R.sup.1, R.sup.2 and R.sup.3 represent each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Ar.sup.1 and Ar.sup.2 represent each ##STR8## wherein R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21 and R.sup.22 represent each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, a halogen atom, ##STR9## wherein R.sup.23 and R.sup.24 represent each an alkyl group, an aralkyl group or a phenyl group, --OR.sup.25 wherein R.sup.25 represents an alkyl group, an aralkyl group or a phenyl group, a hydroxyl group, an aralkyl group, a phenyl group, --R.sup.26 COOR.sup.27 wherein R.sup.26 represents an alkylene group and R.sup.27 represents an alkyl group, --COOR.sup.28 wherein R.sup.28 represents an alkyl group, --R.sup.29 OCOR.sup.30 wherein R.sup.29 represents an alkylene group and R.sup.30 represents an alkyl group, or --OCOR.sup.31 wherein .sup.31 represents an alkyl group; provided, when Ar.sup.1 represents ##STR10## (wherein R and R' represent each an alkyl group having 1 to 4 carbon atoms), n is 0 or 1 and m is 0 or 1. Preferably, n is 0 and m is 0.
Further, this invention is to provide the bisstyryl compounds represented by the following Formula [III] and the electrophotographic photoreceptors containing the bisstyryl compounds. ##STR11## wherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, Ar.sup.1 and Ar.sup.2 represent each ##STR12## wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19 and R.sup.20 represent each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, a halogen atom, ##STR13## wherein R.sup.21 and R.sup.22 represent each an alkyl group, an aralkyl group or a phenyl group, --OR.sup.23 wherein R.sup.23 represents an alkyl group, an aralkyl group or a phenyl group, a hydroxyl group, an aralkyl group, a phenyl group, --R.sup.24 COOR.sup.25 wherein R.sup.24 represents an alkylene group and R.sup.25 represents an alkyl group, --COOR.sup.26 wherein R.sup.26 represents an alkyl group, --R.sup.27 OCOR.sup.28 wherein R.sup.27 represents an alkylene group and R.sup.28 represents an alkyl group, or --OCOR.sup.29 wherein R.sup.29 represents an alkyl group; provided, Ar.sup.1 and Ar.sup.2 shall not represent each ##STR14## (non-substituted), at the same time, and when Ar.sup.1 represents ##STR15## R and/or R' represent each the substituent represented by the above-denoted R.sup.2, R.sup.3, R.sup.4, R.sup.5 or R.sup.6, and when R and R' represent each an alkyl group having 1 to 4 carbon atoms, n is 1 and m is 0 or 1. Regarding Ar.sup.1 and Ar.sup.2, a preferred combination is that Ar.sup.1 represents a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms and Ar.sup.2 represents a non-substituted phenyl group. More preferably, Ar.sup.1 is a substituted with a methyl group, and most preferably is a para-methyl group.
The above-mentioned substituents for the compounds of the invention represented by the above-given formulas include, for example, an alkyl group such as those of methyl, ethyl, propyl and butyl; an alkoxy group such as those of methoxy, ethoxy and propoxy; a halogen atom such as those of fluorine, chlorine and iodine; a dialkylamino group such as those of diethylamine; a diaralkylamino group such as those of diethylphenylamine; a diallylamino group such as those of diphenylamine; a diarylamino group; an ester group such as those of oxycarbonylmethyl; a phenoxy group; a phenyl group; a cyano group; an acyl group such as those of carbonylethyl; a hydroxy group; and a trifluoromethyl group.
Ar.sup.1 and Ar.sup.2 in the formulae I, II and III, preferably are phenyl groups. And when it is substituted, the substituent preferably is a methyl group.
The compounds of the invention represented by the above-given Formulas [I], [II] and [III] are each characterized in the following features (A) through (C) and are each suitable for the carrier transporting materials of an electrophotographic photoreceptor.
(A) The photoreceptivity and durability can be improved, because the compounds are bisstyryl compounds each having a substituent in the molecules thereof. When the electrophotographic photoreceptor is incorporated into a copier or a printer and is then used repeatedly therein, an excellent image can be provided without producing any image defect and any image failure, such as white-dots, black-dots, fog and density lowering, because the electric-charge potential variations can be reduced;
(B) When it is incorporated into a high-speed copier or printer and is then used repeatedly, an excellent image can be provided without producing any image defect or image failure, because the residual potential thereof can also be reduced;
(C) The synthesis thereof can also be easier, because it is a bisstyryl compound.
The typical compounds of the invention Nos. 1 through 87 will be collectively exemplified later.
Next, the synthesis examples of the compounds represented by Formula [I] will now be detailed. The outlines of the synthesis formula will also be given below.
Synthesis Example 1: Synthesis of Exemplified Compound No.6
Formyl substance 3 was synthesized in the known procedures.
Potassium carbonate (manufactured by Kanto Chemical Co.) (in a mol ratio of 2) and copper powder (manufactured by Kanto Chemical Co.) (in a mol ratio of 0.2) were added into 2,4-dimethyl aniline (manufactured by Aldrich Co.) 1 (in a mol ratio of 1) and iodobenzene (manufactured by Tokyo Kasei Co.) (in a mol ratio of 2.5), and the resulting mixture was reacted at an internal temperature within the range of 190.degree. to 210.degree. C. for 50 hours. After the resulting reactant was after-treated and then column-refined, 2,4-dimethyl triphenyl amine 2 was obtained in a yield of 80%, (in Ullmann's reaction).
N,N-dimethyl formamide (manufactured by Kanto Chemical Co.) (in a mol ratio of 4) and phosphorus oxychloride (manufactured by Wako Junyaku Ind. Co.) (in a mol ratio of 3) were added into 2,4-dimethyl triphenyl amine 2 (in a mol ratio of 1), and the resulting mixture was reacted at an internal temperature within the range of 70.degree. to 90.degree. C. for 24 hours. After the resulting reactant was after-treated and then column-refined, N,N-bis(4-formyl-phenyl)-2,4-dimethyl aniline 3 was obtained in a yield of 60%, (in Wilsmyer's reaction).
Diethyl phosphonate substance 7 was synthesized in the known procedures. 4-methyl benzophenone (manufactured by Aldrich Co.) 4 (in a mol ratio of 1) was added into methanol (manufactured by Kanto Chemical Co.) and sodium bolohydride (manufactured by Kanto Chemical Co.) (in a mol ratio of 0.5) was then added thereinto. The resulting mixture was reacted at an internal temperature within the range of 10.degree. to 20.degree. C. for 5 hours. After the resulting reactant was after-treated and then column-refined, hydroxy substance 5 was obtained in a yield of 95%, (in a reduction reaction).
Hydroxy substance 5 (in a mol ratio of 1) was added into toluene (manufactured by Wako Junyaku Ind. Co.) (in a mol ratio of 1.2). The resulting mixture was reacted at an internal temperature within the range of 10.degree. to 20.degree. C. for 2 hours. After the resulting reactant was after-treated, chlor substance 6 was obtained in a yield of 95%, (in a substitution reaction).
Triethyl phosphite (manufactured by Kanto Chemical Co.) (in a mol ratio of 1.2) was added into chlor substance 6 (in a mol ratio of 1). The resulting mixture was reacted at an internal temperature within the range of 140.degree. to 160.degree. C. for 10 hours. After the resulting reactant was after-treated and then distillation-refined, diethyl phosphonate substance 7 was obtained in a yield of 93%, (in a diethyl phosphonate reaction).
A carrier transporting material (hereinafter abbreviated to as CTM) was synthesized by making use of the compounds obtained in the above-described procedures as the raw materials thereof.
N,N-bis(4-formyl-phenyl)-2,4-dimethyl aniline 3 of 10 g (in 0.033 mols) and 1-(4-methyl-phenyl)-1-phenyl-diethyl methyl phosphonate 7 of 21 g (in 0.066 mols) were dissolved in toluene (manufactured by Wako Junyaku Ind. Co.) of 50 ml. Sodium methoxide (manufactured by Kanto Chemical Co.) of 3.6 g (in 0.0660 mols) was added into toluene of 50 ml and the resulting mixed solution was added into the former solution while keeping an internal temperature of not higher than 25.degree. C. with cooling them with ice. After that, the resulting mixture was stirred at room temperature for 3 hours. Then, 100 ml of water was added thereinto, and the resulting toluene layer was washed. The remaining water was removed from the toluene layer with the use of sodium sulfate (manufactured by Kanto Chemical Co.) and the solvents were distilled off. After the resulting residuals were column-refined with silica, the objective exemplified compound No. 6 of 16 g (in 0.023 mols) in the form of yellow-white crystals was obtained in a yield of 71%.
The melting point thereof was within the range of 100.degree. to 114.degree. C. and the elementary analyzed value thereof was a follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%) 91.10 6.71 2.10Calculated value (%): 91.27 6.60 2.13______________________________________
IR data of No.6 (for the spectra thereof, refer to FIG. 1) 1500 cm.sup.-1 /S (Strong: and so forth).
Synthesis Example 2: Synthesis of Exemplified Compound No. 3
Exemplified compound No. 3 of 17.4 g (in 0.026 mols) in the form of yellow-white crystals was obtained in a yield of 80% in the same manner as in Synthesis Example 1, except that 2,4-dimethyl triphenyl amine used in Synthesis Example 1 was replaced by 2,3-dimethyl triphenyl amine.
The melting point thereof was within the range of 102.degree. to 110.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.12 6.80 2.05Calculated value (%): 91.27 6.60 2.13______________________________________
IR data of No.3 (for the spectra thereof, refer to FIG. 2) 1500 cm.sup.-1 /S,
Synthesis Example 3: Synthesis of Exemplified Compound No.2
Exemplified compound No.2 of 16.5 g (in 0.025 mols) in the form of yellow-white crystals was obtained in a yield of 82% in the same manner as in Synthesis Example 1, except that 2,4-dimethyl triphenyl amine and 4-methyl benzophenone used in Synthesis Example 1 were replaced by 2,3-dimethyl triphenyl amine and 3-methyl benzophenone, respectively.
The melting point thereof was within the range of 108.degree. to 115.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.09 6.70 2.07Calculated value (%): 91.27 6.60 2.13______________________________________
Synthesis Example 4: Synthesis of Exemplified Compound No.9
Exemplified compound No.9 of 16.8 g (in 0.026 mols) in the form of yellow-white crystals was obtained in a yield of 80% in the same manner as in Synthesis Example 1, except that 2,4-dimethyl aniline used in Synthesis Example 1 was replaced by 2,5-dimethyl dimethyl aniline.
The melting point thereof was within the range of 102.degree. to 105.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.05 6.81 1.95Calculated value (%): 91.27 6.60 2.13______________________________________
Synthesis Example 5: Synthesis of Exemplified Compound No.10
Exemplified compound No.10 of 12.4 g (in 0.019 mols) in the form of yellow-white crystals was obtained in a yield of 57% in the same manner as in Synthesis Example 1, except that 4-methyl benzophenone and 2,4-dimethyl aniline each used in Synthesis Example 1 were replaced by 2-methyl benzophenone and 2,6-dimethyl aniline, respectively.
The melting point thereof was within the range of 100.degree. to 103.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.18 6.65 2.10Calculated value (%): 91.27 6.60 2.13______________________________________
Next, the typical compounds No.(1) through No.(70) represented by Formula [II] will be collectively exemplified later.
The synthesis examples of the compounds represented by Formula [II] will now be detailed.
Synthesis Example 6: Synthesis of Exemplified Compound No.(22)
Exemplified compound No.(22) of 22 g (in 0.026 mols) in the form of yellow-white crystals was obtained in a yield of 79% in the same manner as in Synthesis Example 1, except that 2,4-dimethyl triphenyl amine and 1-(4-methyl-phenyl)-1-phenyldiethyl methylphosphonate each used in Synthesis Example 1 were replaced by 2,3,6-trimethyl-triphenyl amine and dinaphthyl-diethyl methyl phosphonate, respectively.
The melting point thereof was within the range of 157.degree. to 159.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 92.245 5.973 1.687Calculated value (%): 92.489 5.851 1.659______________________________________
Synthesis Example 7: Synthesis of Exemplified Compound No.(53)
Exemplified compound No.(53) of 18 g (in 0.025 mols) in the form of yellow-white crystals was obtained in a yield of 76% in the same manner as in Synthesis Example 1, except that 2,4-dimethyl triphenyl amine and 1-(4-methyl-phenyl)-1-phenyldiethyl methyl phosphonate each used in Synthesis Example 1 were replaced by 2,4,6-trimethyl-triphenyl amine and 1-(4-chloro-phenyl)-1-phenyl-diethyl methyl phosphonate, respectively.
The melting point thereof was within the range of 138.degree. to 141.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 82.614 5.537 1.902Calculated value (%): 82.572 5.471 1.965______________________________________
Synthesis Example 8: Synthesis of Exemplified Compound No. (11)
Exemplified compound No.11 of 14.8 g (in 0.023 mols) in the form of yellow-white crystals was obtained in a yield of 70% in the same manner as in Synthesis Example 1, except that 2,4-dimethyl triphenyl amine and 1-(4-methyl-phenyl)-1-phenyl-diethyl methyl phosphonate each used in Synthesis Example 1 were replaced by 2,4,6-trimethyl-triphenyl amine and diphenyl-diethyl methyl phosphonate, respectively.
The melting point thereof was within the range of 174.degree. to 177.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.270 6.627 2.098Calculated value (%): 91.405 6.409 2.175______________________________________
IR data of No.(11) (for the spectra thereof, refer to FIG. 3) 1500 cm.sup.-1 :S.
Synthesis Example 9: Synthesis of Exemplified Compound No.(14)
Exemplified compound No.(14) of 14.1 g (in 0.021 mols) in the form of yellow-white crystals was obtained in a yield of 64% in the same manner as in Synthesis Example 8, except that diphenyl-diethyl methyl phosphonate used in Synthesis Example 8 was replaced by 1-(4-methyl-phenyl)-1-phenyl-diethyl methyl phosphonate.
The melting point thereof was within the range of 121.degree. to 125.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.197 6.823 2.008Calculated value (%): 91.165 6.751 2.085______________________________________
IR data of No.(11) (for the spectra thereof, refer to FIG. 4) 1500 cm.sup.-1 : S.
Synthesis Example 10: Synthesis of Exemplified Compound No.(1)
Exemplified compound No.(1) of 12.2 g (in 0.019 mols) in the form of yellow-white crystals was obtained in a yield of 58% in the same manner as in Synthesis Example 8, except that N,N-bis-(4-formyl-phenyl)-2,4,6-trimethyl amine (corresponding to 3 of Synthesis Example 1) used in Synthesis Example 8 was replaced by N,N-bis-(4-formyl-phenyl)-2,3,6-trimethyl amine.
The melting point thereof was within the range of 122.degree. to 125.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.267 6.535 2.198Calculated value (%): 91.405 6.409 2.175______________________________________
Synthesis Example 11: Synthesis of Exemplified Compound No.(20)
Exemplified compound No.(20) of 14.7 g (in 0.021 mols) in the form of yellow-white crystals was obtained in a yield of 64% in the same manner as in Synthesis Example 8, except that diphenyl-diethyl methyl phosphonate used in Synthesis Example 8 was replaced by di(4-methyl-phenyl)-diethyl methylphosphonate.
The melting point thereof was within the range of 169.degree. to 173.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 90.877 7.149 1.983Calculated value (%): 90.943 7.056 2.001______________________________________
Next, the typical compounds No. [1] through [155] represented by Formula [III] will be collectively exemplified later.
The synthesis examples of the compounds represented by Formula [III] will now be detailed.
Synthesis Example 12: Synthesis of Exemplified Compound No.[21]
Exemplified compound No.[21] of 13.1 g (in 0.020 mols) in the form of yellow-white crystals was obtained in a yield of 60% in the same manner as in Synthesis Example 1, except that N,N-bis(4-formyl-phenyl)-2,4-dimethyl amine used in Synthesis Example 1 was replaced by N,N-bis(4-formyl-phenyl)-4-ethyl aniline.
The melting point thereof was within the range of 94.degree. to 100.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.2828 6.5880 2.1281Calculated value (%): 91.2831 6.5879 2.1290______________________________________
IR data of No.[21] (for the spectra thereof, refer to FIG. 5).
Synthesis Example 13: Synthesis of Exemplified Compound No.[3]
Exemplified compound No.[3] of 17.7 g (in 0.027 mols) in the form of yellow-white crystals was obtained in a yield of 70% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by o-ethyl aniline.
The melting point thereof was within the range of 90.degree. to 93.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.2833 6.5876 2.1281Calculated value (%): 91.2831 6.5879 2.1290______________________________________
Synthesis Example 14: Synthesis of Exemplified Compound No.[12]
Exemplified compound No.[12] of 16.4 g (in 0.025 mols) in the form of yellow-white crystals was obtained in a yield of 65% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by m-ethyl aniline.
The melting point thereof was within the range of 93.degree. to 98.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.2829 6.5878 2.1293Calculated value (%): 91.2831 6.5879 2.1290______________________________________
Synthesis Example 15: Synthesis of Exemplified Compound No.[30]
Exemplified compound No.[30] of 18.8 g (in 0.028 mols) in the form of yellow-white crystals was obtained in a yield of 85% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by o-n-propyl aniline.
The melting point thereof was within the range of 91.degree. to 94.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1644 6.7508 2.0850Calculated value (%): 91.1651 6.7504 2.0846______________________________________
Synthesis Example 16: Synthesis of Exemplified Compound No. [39]
Exemplified compound No.[39] of 14.1 g (in 0.021 mols) in the form of yellow-white crystals was obtained in a yield of 63% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by m-n-propyl aniline.
The melting point thereof was within the range of 87.degree. to 92.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1653 6.7481 2.0832Calculated value (%): 91.1651 6.7504 2.0846______________________________________
Synthesis Example 17: Synthesis of Exemplified Compound No.[48]
Exemplified compound No.[48] of 17.5 g (in 0.026 mols) in the form of yellow-white crystals was obtained in a yield of 79% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by p-n-propyl aniline.
The melting point thereof was within the range of 89.degree. to 92.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1629 6.7511 2.0821Calculated value (%): 91.1651 6.7504 2.0846______________________________________
Synthesis Example 18: Synthesis of Exemplified Compound No.[57]
Exemplified compound No.[57] of 13.4 g (in 0.020 mols) in the form of yellow-white crystals was obtained in a yield of 61% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by o-isopropyl aniline.
The melting point thereof was within the range of 88.degree. to 90.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1659 6.7481 2.0836Calculated value (%): 91.1651 6.7504 2.0846______________________________________
Synthesis Example 19: Synthesis of Exemplified Compound No.[66]
Exemplified compound No.[66] of 14.1 g (in 0.021 mols) in the form of yellow-white crystals was obtained in a yield of 64% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by m-isopropyl aniline.
The melting point thereof was within the range of 93.degree. to 99.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1593 6.7421 2.0799Calculated value (%): 91.1651 6.7504 2.0846______________________________________
Synthesis Example 20: Synthesis of Exemplified Compound No [75]
Exemplified compound No.[75] of 18.1 g (in 0.027 mols) in the form of yellow-white crystals was obtained in a yield of 82% in the same manner as in Synthesis Example 12, except that p-ethyl aniline used in Synthesis Example 12 was replaced by p-isopropyl aniline.
The melting point thereof was within the range of 95.degree. to 102.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1623 6.7488 2.0841Calculated value (%): 91.1651 6.7504 2.0846______________________________________
Synthesis Example 21: Synthesis of Exemplified Compound No.[24]
Exemplified compound No.[24] of 15.1 g (in 0.022 mols) in the form of yellow-white crystals was obtained in a yield of 66% in the same manner as in Synthesis Example 12, except that 4-methyl benzophenone used in Synthesis Example 12 was replaced by 4,4'-dimethyl benzophenone.
The melting point thereof was within the range of 112.degree. to 116.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.1010 6.9008 2.0311Calculated value (%): 91.0519 6.9062 2.0419______________________________________
Synthesis Example 22: Synthesis of Exemplified Compound No.[60]
Exemplified compound No.[60] of 16.8 g (in 0.024 mols) in the form of yellow-white crystals was obtained in a yield of 73% in the same manner as in Synthesis Example 12, except that p-ethyl aniline and 4-methyl benzophenone each used in Synthesis Example 12 were replaced by o-isopropyl aniline and 4,4'-dimethyl benzophenone, respectively.
The melting point thereof was within the range of 109.degree. to 115.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 90.8 7.03 2.0100Calculated value (%): 90.9432 7.0558 2.0010______________________________________
Synthesis Example 23: Synthesis of Exemplified Compound No. [136]
Exemplified compound No.[136] of 16.1 g (in 0.024 mols) in the form of yellow-white crystals was obtained in a yield of 74% in the same manner as in Synthesis Example 12, except that 4-methyl benzophenone used in Synthesis Example 12 was replaced by 4-ethyl benzophenone.
The melting point thereof was within the range of 112.degree. to 118.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 91.10 6.90 2.00Calculated value (%): 91.05 6.9062 2.042______________________________________
Synthesis Example 24: Synthesis of Exemplified Compound No.[140]
Exemplified compound No.[140] of 14.9 g (in 0.022 mols) in the form of yellow-white crystals was obtained in a yield of 68% in the same manner as in Synthesis Example 12, except that 4-methyl benzophenone used in Synthesis Example 12 was replaced by 4-bromo benzophenone.
The melting point thereof was within the range of 121.degree. to 124.degree. C. and the elementary analyzed value thereof was as follows.
______________________________________ C (carbon) H (hydrogen) N (nitrogen)______________________________________Measured value (%): 73.12 4.74 1.71Calculated value (%): 73.19 4.73 1.77______________________________________
When an electrophotographic photoreceptor contains the compound represented by the afore-given Formulas [I] through [III] as the carrier transporting material, they may have the configurations shown in FIGS. 6 through 11.
In FIGS. 6 and 7, to be more concrete, electroconductive support 1 is provided thereonto with photoreceptive layer 4 comprising carrier generating layer 2 containing a carrier generating material as the principal component thereof and carrier transporting layer 3 containing a carrier transporting material relating to the invention as the principal component thereof.
Photoreceptive layer 4 may also be interposed between electroconductive support 1 and interlayer 5 provided onto the support 1.
When photoreceptive layer 4 has a double-layered structure as mentioned above, a photoreceptor having excellent electrophotographic characteristics can be prepared.
In the invention, as shown in FIGS. 10 and 11, it is also allowed that electroconductive support 1 may be provided thereonto, directly or through interlayer 5 with photoreceptive layer 4 comprising layer 6 containing a carrier transporting material as the principal component thereof and dispersed therein with a carrier generating material.
In the invention, as indicated by the imaginary line shown in FIG. 9, protective layer 7 may also be provided as the outermost layer.
A photoreceptive layer is formed of various combinations of binders, because the compounds of the invention represented by Formulas [I] through [III] lack a coat-forming function in themselves.
Any desired binders can be used as the above-mentioned binders. Among them, it is preferable to use a high-molecular polymers having a hydrophobic property, a high permittivity and an electric-insulating film-forming property.
The above-mentioned high-molecular polymers include, for example, the following polymers. There is, however, no limitation thereto.
(P-1) polycarbonate
(P-2) polyester
(P-3) methacrylic resin
(P-4) acrylic resin
(P-5) polyvinyl chloride
(P-6) polyvinylidene chloride
(P-7) polystyrene
(P-8) polyvinyl acetate
(P-9) a styrene-butadiene copolymer
(P-10) a vinylidene chloride-acrylonitrile copolymer
(P-11) a vinyl chloride-vinyl acetate copolymer
(P-12) a vinyl chloride-vinyl acetate-maleic anhydride copolymer
(P-13) silicone resin
(P-14) silicone-alkyd resin
(P-15) phenol formaldehyde resin
(P-16) styrene-alkyd resin
(P-17) poly-N-vinyl carbazole
(P-18) polyvinyl butyral
(P-19) polyvinyl formal
The above-given binder resins may be used independently or in combination in the forms of the mixtures thereof.
There is no special limitation to the CTMs applicable to the invention in combination. Among them, the examples thereof include the following compounds; namely, an oxazole derivative, an oxadiazole derivative, a thiazole derivative, a thiadiazole derivative, a triazole derivative, an imidazole derivative, an imidazolone derivative, an imidazolidine derivative, a bisimidazolidine derivative, a styryl compound, a hydrazone compound, a pyrazoline derivative, an amine derivative, an oxazolone derivative, a benzothiazole derivative, a benzoimidazole derivative, a quinazoline derivative, a benzofran derivative, an acridine derivative, a phenazine derivative, an aminostilbene derivative, a poly-N-vinylcarbazole, a poly-1-vinylpyrene and a poly-9-vinylanthracene.
The CTMs applicable to the invention include, preferably, those excellent in transporting function for a hole produced by irradiating light and suitable for a combination thereof with a later-described organic pigment applicable to the invention.
The carrier generating materials applicable to the carrier generating layers of the photoreceptive layers relating to the invention include, for example, the following materials.
(1) Azo type dyes such as a monoazo dye, a bisazo dye and a trisazo dye;
(2) Perylene type dyes such as a perylenic anhydride and perylenic imide;
(3) Indigo type dyes such as an indigo and a thioindigo;
(4) Polycyclic quinones such as an anthraquinone, a pyrene quinone and a flavanthrone;
(5) Quinacrydone type dyes;
(6) Bisbenzoimidazole type dyes;
(7) Indanthrone type dyes;
(8) Squarylium type dyes;
(9) Cyanine type dyes;
(10) Azulenium type dyes;
(11) Triphenyl methane type dyes;
(12) Amorphous silicon;
(13) Phthalocyanine type pigments such as a metal phthalocyanine and a non-metal phthalocyanine;
(14) Selenium, selenium-tellurium and selenium-arsenic;
(15) AdS and AdSe; and
(16) Pyrylium salt dyes and thiapyrylium salt dyes.
The above-given carrier generating materials can be used not only independently but also in combination in the forms of the mixtures thereof.
The electrophotographic photoreceptors relating to the invention are preferable to be applied with organic type pigments such as a fluorenone type bisazo pigment, a fluorenylidene type bisazo pigment and a polycyclic quinone pigment, as the CGMs thereof. In particular, when applying the fluorenone type bisazo pigments represented by the later-given Formula [F.sub.1 ], fluorenylidene type bisazo pigments or polycyclic quinone pigments to the invention, the remarkably improved effects of photoreceptivity and durability can be displayed.
The typical examples [F.sub.1 -1 through F.sub.1 -24] of the fluorenone type bisazo pigments applicable to the invention will be given later. It is, however, to be understood that the invention shall not be limited thereto.
The fluorenone type bisazo pigments represented by the later-given Formula [F.sub.1 ] which are applicable to the invention can be synthesized in any well-known processes including, for example, the processes described in Japanese Patent Application No. 62-304862/1987.
The fluorenylidene type bisazo pigments applicable to the invention are represented by the later-given Formula [F.sub.2 ].
The typical examples of the bisazo pigments represented by Formula [F.sub.2 ], which are effectively applicable to the invention, may include, for example, those represented by the chemical structures [F.sub.2 -1] through [F.sub.2 -7] which will be given later. It is, however, to be understood that the bisazo pigments applicable to the invention shall not be limited thereto.
The polycyclic quinone pigments applicable to the invention are represented by Formulas [Q.sub.1 ] through [Q.sub.3 ] which will be given later.
The typical examples of the polycyclic quinone pigments represented by later-given Formulas [Q.sub.1 ] through [Q.sub.3 ], which are applicable to the invention, will be given later. However, the invention shall not be limited thereto.
The typical examples of the anthanthrone pigments represented by Formula [Q.sub.1 ] include those represented by the later-given formulas [Q.sub.1 -1] through [Q.sub.1 -6].
The typical examples of the dibenzypyrene quinone pigments represented by Formula [Q.sub.2 ] include those represented by the later-given formulas [Q.sub.2 -1] through [Q.sub.2 -5].
The typical examples of the pyranthrone pigments represented by Formula [Q.sub.3 ] include those represented by the later-given formulas [Q.sub.3 -1] through [Q.sub.3 -4].
The polycyclic quinone pigments represented by Formulas [Q.sub.1 ] through [Q.sub.3 ], which are applicable to the invention, can readily be synthesized in any well-known processes.
The non-metal phthalocyanine type pigments applicable to the invention include all the non-metal phthalocyanines each having photoconductivity and the derivatives thereof. For example, they include those of the .alpha. type, .beta. type, .tau. and .tau.' type, .eta. and .eta.' type, X type and those having the crystal forms described in JP OPI Publication No. 62-103651/1987 and the derivatives thereof. Among them, those of the .tau., X and K/R-X types are preferably used.
The X type non-metal phthalocyanines are described in U.S. Pat. No. 3,357,989 and the .tau. type non-metal phthalocyanines are described in JP OPI Publication No. 58-182639/1983.
As described in JP OPI Publication No. 62-103651/1987, the K/R-X type phthalocyanines are each characterized in having a principal peaks at a Bragg's angles (of 2.theta..+-.0.2.degree.) of 7.7.degree., 9.2.degree., 16.8.degree.,17.5.degree., 22.4.degree. and 28.8.degree. with respect to the X-rays of CuK.alpha. at 1.541 .ang., a peak intensity ratio within the range of 0.8 to 1.0 at 16.8.degree. with respect to the peak intensity at 9.2.degree. and a peak intensity ratio of not lower than 0.4 at 28.8.degree. with respect to the peak intensity at 22.4.degree..
The oxytitanyl phthalocyanines applicable to the invention are each represented by the Formula [TP] which will be given later.
Those applicable to the invention include ones having different crystal forms, which are disclosed in the following patent publications, namely, JP OPI Publication Nos. 61-239248/1986, 62-272272/1987, 62-116158/1987, 64-17066/1989, 2-28265/1990 and 2-215866/1990.
The dispersion media for the organic type pigments applicable to the invention include, for example, the well-known dispersion media such as a methyl ethyl ketone.
In the invention, one or not less than two kinds of well-known electron-acceptant material can be contained in a photoreceptive layer. Such as electron-acceptant material as mentioned above is to be added in a proportion thereof to an organic type pigment applicable to the invention=0.01.about.200:100 by weight and, preferably, 0.1.about.100:100 by weight. And, the electron-acceptant material is to be added in a proportion thereof to whole CTM=0.01.about.100:100 by weight and, preferably, 0.1.about.50:100 by weight.
For the purpose of improving the electric-charge generating function of a carrier generating material (hereinafter abbreviated to as CGM), an organic amines can be added into a photoreceptive layer. Among these organic amines, secondary amines are preferable to be added thereto. These compounds are given in, for example, JP OPI Publication Nos. 59-218447/1984 and 62-8160/1987.
For the purpose of preventing deterioration by ozone, an antioxidant such as those given in JP OPI Publication No. 63-18354/1988 may be added in the photoreceptive layers. Such an antioxidant as mentioned above is to be added in an amount within the range of 0.1 to 100 parts by weight per 100 parts by weight of CTM, desirably, 1 to 50 parts by weight and, preferably 5 to 25 parts by weight.
Further, if required, for the purpose of protecting a photoreceptive layer, an UV absorbent may be added and a color-sensitivity correction dye may also be added.
An interlayer may be interposed between a photoreceptive layer and a support. The interlayer can function as an adhesion layer or a blocking layer.
In the invention, when a photoreceptive layer has a double-layered structure as shown in FIG. 6, a carrier generating layer (hereinafter abbreviated to as a CGL) can be formed, in the following method, directly over an electroconductive support or a carrier transporting layer (hereinafter abbreviated to as a CTL) or, if required, over an interlayer such as an adhesion layer or a blocking layer interposed therebetween.
(1) A vacuum-evaporation method;
(2) A method in which a solution prepared by dissolving a CGM in a suitable solvent is coated; and
(3) A method in which a dispersion solution prepared by making a CGM super-finely grained in a dispersion medium by making use of a ball-mill or a sand-grinder or, if required a dispersion solution prepared by mixedly dispersing a CGM with a binder in a dispersion medium.
To be more concrete, it is allowed to use any desired gas-phase segmentary methods such as a vacuum-evaporation method, a spattering method and a CVD method or any desired coating methods such as a dip-coating method, a spray-coating method, a blade-coating method and a roller-coating method.
The CGLs formed in the above-mentioned manner are each to have a thickness within the range of, desirably, 0.01 .mu.m to 5 .mu.m and, preferably, 0.05 .mu.m to 3 .mu.m.
The above-mentioned CTLs can also be formed in the same manner as in CGLs. The thickness of such a CTL may be so varied as to meet the requirements, however, it is usually within the range of, preferably, 5 .mu.m to 60 .mu.m.
The CTL is composed of a binder in a proportion within the range of, preferably, 1 to 5 parts by weight per one part by weight of the CTM of the invention. When forming photoreceptive layer 4 in which a finely grained CGM is dispersed, it is preferred to use a binder in a proportion of not more than 5 parts by weight to one part by weight of CGM.
When composing a CGL dispersed in a binder, it is preferred to use the binder in a proportion of not more than 5 parts by weight to one part by weight of CGM.
The electrophotographic photoreceptors relating to the invention have each the above-described composition. Therefore, as is apparent from the examples given later, they are excellent in electric-charging characteristics, photoreceptive characteristics and image-forming characteristics and, particularly, few in fatigue and deterioration even when they are repeatedly used, so that the durability can be excellent.
In addition to the above, the electrophotographic photoreceptors relating to the invention can widely be applied to an electrophotographic copier and, besides, to many applicable fields such as the photoreceptors for a printer in which a laser, cathode-ray tube or light emitting device (LED) is used as the light source thereof. Further, the invention can also be applied to the other devices than the photoreceptors and to an electroluminescence (EL).
EXAMPLES
The examples of the invention will now be more detailed. It is, however, to be understood that the embodiments of the invention shall not be limited thereto.
EXAMPLE 1
A polyamide was prepared by copolymerizing .epsilon.-amino-caproic acid, adipic acid and N-(.beta.-aminoethyl)piperazine in a monomer composition proportion of 1:1:1. The resulting polyamide of 30 g was added into 200 ml of methanol EL standard (manufactured by Kanto Chemical Co.) of 800 ml, which was heated at 50.degree. C. Then, the resulting mixture was dip-coated over an aluminium-made drum having a diameter of 80 mm, so that a 0.6 .mu.m-thick interlayer was formed.
Next, 20 g of a fluorenone type bisazo pigment (that was Exemplified Compound F.sub.1 -23) as a CGM and 10 g of polyvinyl butyral resin, Eslec BX-1 (manufactured by Sekisui Chemical Co.) as a binder were dissolved in 1000 ml of methyl ethyl ketone (manufactured by Kanto Chemical Co.). The resulting solution was milled by a sand-mill for 24 hours, so that a CGL coating solution was obtained. The CGL coating solution was dip-coated over the above-prepared interlayer, so that a 0.2 .mu.m-thick CGL was formed.
After that, 140 g of Exemplified Compound No.1 and 165 g of polycarbonate resin, `Eupiron Z-200` (manufactured by Mitsubishi Gas-Chemical Co., Ltd.) were dissolved in 1000 ml of 1,2-dichloroethane, Special Class, (manufactured by Kanto Chemical Co.), so that a CTL coating solution was obtained.
The resulting CTL coating solution was dip-coated over the above-mentioned CGL and the resulting coated CGL was dried at 100.degree. C. for 1 hour, so that a 23 .mu.m-thick CTL was formed. In the manner mentioned above, the interlayer, the CGL and the CTL were laminated in this order, so that photoreceptive layer 1 was formed.
EXAMPLES 2 through 10
Photoreceptors 2 through 10 were each prepared in the same manner as in Example 1, except that the CGM and CTM used each in Example 1 were replaced by the exemplified compounds as shown in the following Table-1, respectively.
COMPARATIVE EXAMPLES 1 and 2
As shown in the following Table-1, the comparative photoreceptors were each prepared in the same manner as in Example 1, except that the CTM used in Example 1 was replaced by comparative compounds (1) and (2) which will be given later, respectively.
EXAMPLE 11
The interlayer was prepared in the same manner as in Example 1.
Polycyclic quinone type pigment (that was Exemplified Compound Q.sub.1 -3) of 20 g as the CGM and polycarbonate resin C-1300 (manufactured by Teijin Chemical Ind. Co.) of 10 g were each dissolved in 1,2-dichloroethane Special Class (manufactured by Kanto Chemical Co.) and the resulting solution was milled by a ball-mill for 30 hours, so that a CGL coating solution was obtained. The resulting CGL coating solution was dip-coated over the aforementioned interlayer, so that a 0.6 .mu.m-thick CGL was formed.
Next, photoreceptor 11 was prepared by laminating a CTL in the same manner as in Example 1.
EXAMPLES 12 through 20
Photoreceptors 12 through 20 were each prepared in the same manner as in Example 11, except that the CTM used in Example 11 was replaced by the exemplified compounds each as shown in the following Table-2, respectively.
COMPARATIVE EXAMPLES 3 and 4
As shown in the following Table-2, comparative photoreceptors 3 and 4 were each prepared in the same manner as in Example 11, except that the CTM used in Example 11 was replaced by comparative compounds (1) and (2), respectively.
EXAMPLE 21
After dissolving 12 g of polyvinyl butyral resin (Eslec BX-1 manufactured by Sekisui Chemical Co.) in 1000 ml of methyl ethyl ketone, the resulting solution was mixed with 5.7 g of Exemplified Compound Q.sub.1 -3 and 0.5 g of Exemplified Compound F.sub.1 -23 each as the CGMs and the resulting mixture was dispersed for 12 hours by making use of a sand-grinder.
The resulting dispersed solution was dip-coated over the interlayer mentioned in Example 1, so that a CGL was formed and, further, the CTL was formed by making use of Exemplified Compound No.2 as the CTM, so that photoreceptor 21 was prepared.
EXAMPLES 22 through 30
Photoreceptors 22 through 30 were each prepared in the same manner as in Example 21, except that the CGM and CTM each used in Example 21 were replaced by the exemplified compounds as shown in the following Table-3, respectively.
COMPARATIVE EXAMPLES 5 and 6
As shown in the following Table-3, comparative photoreceptors 5 and 6 were each prepared in the same manner as in Example 21, except that the CTM used in Example 21 was replaced by comparative compounds (1) and (2), respectively.
EXAMPLE 31
The polyamide of 50 g used in Example 1 was added and dissolved into 800 ml of methanol EL standard (manufactured by Kanto Chemical Co.) which was heated up to 50.degree. C. The resulting solution was cooled down to room temperature and was then added with 200 ml of 1-butanol special class (Kanto Chemical Co.). After that, the resulting solution was dip-coated over an aluminium drum having a diameter of 80 mm, so that a 0.5 .mu.m-thick interlayer was formed.
Next, 40 g of .tau. type non-metal phthalocyanine (.tau.-Pc) as a CGM was added into 2000 ml of methyl ethyl ketone EL standard (manufactured by Kanto Chemical Co.) in which 200 g of silicone resin `KR-5240` (having a solid component of 20%) (manufactured by Kanto Chemical Co.). The resulting solution was dispersed for 4 hours by making use of a sand-grinder, so that a CGL coating solution was obtained. The resulting coating solution was dip-coated over the foregoing interlayer, so that a 0.4 .mu.m -thick CGL was formed.
Thereafter, 135 g of Exemplified Compound (3) and 165 g of polycarbonate `Eupiron Z-200` (manufactured by Mitsubishi Gas-Chemical Co.) were each dissolved in 1000 ml of 1,2-dichlorethane special class (manufactured by Kanto Chemical Co.), so that a CTL coating solution was obtained. The resulting coating solution was dip-coated over the above-mentioned CGL and the resulting coated VGL was dried at 100.degree. C. for 1 hour, so that a 22 .mu.m-thick CTL was obtained. After then, the interlayer, CGL and CTL were each laminated in this order, so that a photoreceptor was prepared.
EXAMPLES 32 through 40
Electrophotoreceptors 32 through 40 were each prepared in the same manner as in Example 31, except that the CGM used in Example 31 was replaced by the exemplified compounds as shown in the following Table-4, respectively.
COMPARATIVE EXAMPLES 7 and 8
The comparative electrophotoreceptors were each prepared in the same manner as in Example 31, except that the CTM used in Example 31 was replaced by Comparative Compound (1) and (2) as shown in the following Table-4, respectively.
EXAMPLE 41
A photoreceptor comprising an interlayer--a CGL--an CTL each laminated in this order was prepared in the same manner as in Example 1, except that an X type non-metal phthalocyanine (X-Pc) was used as the CGM.
EXAMPLES 42 through 50
Photoreceptors 42 through 50 were each prepared in the same manner as in Example 41, except that the CTM used in Example 41 was replaced by the exemplified compounds as shown in the following Table-5, respectively.
COMPARATIVE EXAMPLES 9 and 10
The comparative examples were each prepared in the same manner as in Example 41, except that the CTM used in Example 41 was replaced by Comparative Compounds (1) and (2) as shown in the following Table-5, respectively.
EXAMPLE 51
The photoreceptor comprising an interlayer--a CGL--a CTL laminated in this order was prepared in the same manner as in Example 1, except that the CGM used in Example 1 was replaced by the Y type oxytitanium phthalocyanine (Y-TiOPc) [for which, refer to The Bulletin of The Society of Electrophotography, 250(2), 29(2). 1990].
EXAMPLES 52 through 60
Photoreceptors 52 through 60 were each prepared in the same manner as in Example 51, except that the CTM used in Example 51 was replaced by the exemplified compounds as shown in the following Table-6, respectively.
COMPARATIVE EXAMPLES 11 and 12
The comparative photoreceptors were each prepared in the same manner as in Example 51, except that the CTM used in Example 51 was replaced by Comparative Compounds (1) and (2) as shown in the following Table-6, respectively.
EXAMPLE 61
The photoreceptor was prepared in the same manner as in the above-given example, except that the CGM used in the above-given example was replaced by a fluorenylidene type azo CGM.
EXAMPLES 62 through 70
Photoreceptors 62 through 70 were each prepared in the same manner as in Example 61, except that the CGM and CTM each used in Example 61 were each replaced by the exemplified compounds as shown in the following Table-7, respectively.
COMPARATIVE EXAMPLES 13 and 14
The comparative examples were each prepared in the same manner as in Example 61, except that the CTM used in Example 61 was replaced by Comparative Compounds (1) and (2) as shown in the following Table-7, respectively.
TABLE-1______________________________________ PhotoreceptorExample No. No. CGM CTM______________________________________Inventive Inventive Compound F.sub.1 -23 ExemplifiedExample 1 photoreceptor 1 compound 1Inventive Inventive Compound F.sub.1 -23 ExemplifiedExample 2 photoreceptor 2 compound 3Inventive Inventive Compound F.sub.1 -23 ExemplifiedExample 3 photoreceptor 3 compound 6Inventive Inventive Compound F.sub.1 -23 ExemplifiedExample 4 photoreceptor 4 compound 8Inventive Inventive Compound F.sub.1 -1 ExemplifiedExample 5 photoreceptor 5 compound 9Inventive Inventive Compound F.sub.1 -1 ExemplifiedExample 6 photoreceptor 6 compound 17Inventive Inventive Compound F.sub.1 -1 ExemplifiedExample 7 photoreceptor 7 compound 20Inventive Inventive Compound F.sub.1 -1 ExemplifiedExample 8 photoreceptor 8 compound 76Inventive Inventive Compound F.sub.1 -7 ExemplifiedExample 9 photoreceptor 9 compound 50Inventive Inventive Compound F.sub.1 -16 ExemplifiedExample 10 photoreceptor compound 53 10Comparative Comparative Compound F.sub.1 -23 ComparativeExample 1 photoreceptor 1 compound (1)Comparative Comparative Compound F.sub.1 -23 ComparativeExample 2 photoreceptor 2 compound (2)______________________________________
TABLE-2______________________________________ PhotoreceptorExample No. No. CGM CTM______________________________________Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 11 photoreceptor 11 compound 1Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 12 photoreceptor 12 compound 3Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 13 photoreceptor 13 compound 6Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 14 photoreceptor 14 compound 24Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 15 photoreceptor 15 compound 26Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 16 photoreceptor 16 compound 33Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 17 photoreceptor 17 compound 77Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 18 photoreceptor 18 compound 44Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 19 photoreceptor 19 compound 51Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 20 photoreceptor 20 compound 54Comparative Comparative Compound Q.sub.1 -3 ComparativeExample 3 photoreceptor 3 compound (1)Comparative Comparative Compound Q.sub.1 -3 ComparativeExample 4 photoreceptor 4 compound (2)______________________________________
TABLE-3______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 21 F.sub.1 -23 compound 221Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 22 F.sub.1 -23 compound 622Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 23 F.sub.1 -23 compound 923Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 24 F.sub.1 -23 compound 1124Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 25 F.sub.1 -23 compound 1525Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 26 F.sub.1 -23 compound 2126Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 27 F.sub.1 -23 compound 8227Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 28 F.sub.1 -23 compound 3128Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 29 F.sub.1 -7 compound 4229Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 30 F.sub.1 -16 compound 5230Compar- Comparative Compound Q.sub.1 -3, Comparativeative photoreceptor 5 F.sub.1 -23 compound (1)ExampleCompar- Comparative Compound Q.sub.1 -3, Comparativeative photoreceptor 6 F.sub.1 -23 compound (2)Example6______________________________________
TABLE-4______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 31 phthalocyanine compound 331Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 32 phthalocyanine compound 632Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 33 phthalocyanine compound 733Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 34 phthalocyanine compound 934Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 35 phthalocyanine compound 1535Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 36 phthalocyanine compound 2436Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 37 phthalocyanine compound 3137Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 38 phthalocyanine compound 4238Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 39 phthalocyanine compound 8139Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 40 phthalocyanine compound 6740Compar- Comparative .tau. type non-metallic Comparativeative photoreceptor 7 phthalocyanine compound (1)ExampleCompar- Comparative .tau. type non-metallic Comparativeative photoreceptor 8 phthalocyanine compound (2)Example8______________________________________
TABLE-5______________________________________Example PhotoreceptorNo. No CGM CTM______________________________________Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 41 phthalocyanine compound 141Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 42 phthalocyanine compound 242Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 43 phthalocyanine compound 643Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 44 phthalocyanine compound 844Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 45 phthalocyanine compound 945Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 46 phthalocyanine compound 1046Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 47 phthalocyanine compound 2147Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 48 phthalocyanine compound 3148Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 49 phthalocyanine compound 4549Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 50 phthalocyanine compound 5150Compar- Comparative X type non-metallic Comparativeative photoreceptor 9 phthalocyanine compound (1)ExampleCompar- Comparative X type non-metallic Comparativeative photoreceptor 10 phthalocyanine compound (2)Example10______________________________________
TABLE-6______________________________________Example PhotoreceptorNo. No CGM CTM______________________________________Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 51 phthalocyanine compound 151Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 52 phthalocyanine compound 652Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 53 phthalocyanine compound 953Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 54 phthalocyanine compound 1854Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 55 phthalocyanine compound 2155Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 56 phthalocyanine compound 3456Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 57 phthalocyanine compound 4257Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 58 phthalocyanine compound 7858Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 59 phthalocyanine compound 6759Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 60 phthalocyanine compound 7060Compar- Comparative Y type oxytitanium Comparativeative photoreceptor 11 phthalocyanine compound (1)Example11Compar- Comparative Y type oxytitanium Comparativeative photoreceptor 12 phthalocyanine compound (2)Example12______________________________________
TABLE-7______________________________________ PhotoreceptorExample No. No CGM CTM______________________________________Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 61 photoreceptor 61 compound 3Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 62 photoreceptor 62 compound 6Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 63 photoreceptor 63 compound 15Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 64 photoreceptor 64 compound 23Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 65 photoreceptor 65 compound 31Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 66 photoreceptor 66 compound 33Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 67 photoreceptor 67 compound 37Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 68 photoreceptor 68 compound 42Inventive Inventive Compound F.sub.2 -3 ExemplifiedExample 69 photoreceptor 69 compound 50Inventive Inventive Compound F.sub.2 -5 ExemplifiedExample 70 photoreceptor 70 compound 59Comparative Comparative Compound F.sub.2 -6 ComparativeExample 13 photoreceptor 13 compound (1)Comparative Comparative Compound F.sub.2 -6 ComparativeExample 14 photoreceptor 14 compound (2)______________________________________
EVALUATION EXAMPLE 1
The residual potentials Vr were each measured when a series of electric-charging.multidot.Exposing operations were repeated 20,000 times by making use of a copier, modified U-Bix Model 5076 manufactured by Konica Corp. (in which the charging electrode was changed to be negative and the exposure amount was changed into 4.65 lux) and by changing the linear velocities into 3 velocities, namely 240, 330 and 440 mm/sec. The results of the measurements are shown in the following Tables-8 through 10. The residual potentials of the photoreceptors applied with the CTM of the invention did not become intense when the linear velocities were made faster than those of the photoreceptors applied with the comparative compounds, so that an excellent high velocities were shown. In the meanwhile, the initial white-paper potentials (Vw) were each shown in Tables-8 through 10.
EVALUATION EXAMPLE 2
The 100,000 times continuous copying tests were tries by making use of A-4 size regenerated paper and the copier, modified U-Bix Model 5076 manufactured by Konica Corp., which was the same as in Evaluation Example 1. The results thereof are shown in the following Tables-11 through 13. The photoreceptors applied with the compounds of the invention provided excellent images upto the 100,000th copy and, on the other hand, the comparative photoreceptors produced several white-dots in the solid-black image areas after the 20,000 to 30,000th copying tests. The white-dots were evaluated by visually counting the numbers of the white-dots produced on a solid-black image in A-4 size. The results thereof are shown in Tables-11 through 13.
EVALUATION EXAMPLE 3
The resulting electric potential in an unexposed area VH and electric potential in an exposed area VL were each measured at an ordinary temperature (of 25.degree. C.) and a low temperature (of 10.degree. C.) by making use of a digital copier, U-Bix Model 8028 manufactured by Konica Corp. The results thereof are shown in the following Tables-14 through 17.
EVALUATION EXAMPLE 4
The resulting black-dots produced in the white-background of a copied image were evaluated after making use of the digital copier, U-Bix Model 8028 manufactured by Konica Corp., which was the same as that used in the above-described Evaluation Example 3, loading the subject photoreceptor into a developer and then image-copying several times. The results thereof are shown in the following Tables-18 through 21.
The resulting black-dots were evaluated by measuring the dot-sizes and numbers of the black-dots through an image analyzer, `Omnicon Model 300` (manufactured by Shimazu Mfg. Works). The results were judged by counting the numbers of the resulting black-dots having a size .0. of not smaller than 0.05 mm in one cm.sup.2. The judgement criteria of evaluating the black-dots are shown in the following table.
TABLE______________________________________Black spots of not smaller black dotthan .0.0.05 mm in size judgement______________________________________Nil/cm.sup.2 .circleincircle.1.about.3 spots/cm.sup.2 .largecircle.4.about.10 spots/cm.sup.2 .DELTA.Not less than 11 spots/cm.sup.2 X______________________________________
In the table, when a black-dot judgement was resulted to be .circleincircle. and .largecircle., the subject photoreceptor can be put to practical use; when it is resulted to be .DELTA., the subject photoreceptor may sometimes be impractical; and when it was proved to be .times., the subject photoreceptor cannot be practical.
TABLE-8______________________________________ Initial Vr (v) after 20000th repetition white at the following linear velocity paper Repetition Repetition RepetitionPhotoreceptor potential, at 240 at 330 at 440No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 51 10 14 21photoreceptor 1Inventive 52 9 12 19photoreceptor 2Inventive 50 12 16 22photoreceptor 3Inventive 49 13 16 20photoreceptor 4Inventive 52 11 15 21photoreceptor 5Inventive 53 14 15 23photoreceptor 6Inventive 51 15 17 22photoreceptor 7Inventive 55 12 16 25photoreceptor 8Inventive 50 13 16 26photoreceptor 9Inventive 52 14 18 27photoreceptor10Comparative 61 15 38 75photoreceptor 1Comparative 73 17 45 89photoreceptor 2______________________________________
TABLE-9______________________________________ Initial Vr (v) after 20000th repetition white at the following linear velocity paper Repetition Repetition RepetitionPhotoreceptor potential, at 240 at 330 at 440No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 96 10 12 20photoreceptor11Inventive 101 8 11 19photoreceptor12Inventive 97 11 13 19photoreceptor13Inventive 92 15 17 23photoreceptor14Inventive 96 12 16 25photoreceptor15Inventive 98 16 19 24photoreceptor16Inventive 100 13 16 21photoreceptor17Inventive 102 14 16 26photoreceptor18Inventive 104 10 13 22photoreceptor19Inventive 105 15 18 25photoreceptor20Comparative 112 14 37 75photoreceptor 3Comparative 121 15 39 79photoreceptor 4______________________________________
TABLE-10______________________________________ Initial Vr (v) after 20000th repetition white at the following linear velocity paper Repetition Repetition RepetitionPhotoreceptor potential, at 240 at 330 at 440No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 75 10 15 20photoreceptor21Inventive 66 11 15 23photoreceptor22Inventive 76 14 18 24photoreceptor23Inventive 65 12 18 26photoreceptor24Inventive 61 13 19 24photoreceptor25Inventive 63 15 20 23photoreceptor26Inventive 77 16 21 26photoreceptor27Inventive 73 15 20 27photoreceptor28Inventive 71 17 23 28photoreceptor29Inventive 75 18 22 30photoreceptor30Comparative 80 17 45 85photoreceptor 5Comparative 95 18 37 84photoreceptor 6______________________________________
TABLE-11______________________________________ Numbers of Numbers of Numbers of white spots white spots white spots produced produced produced afterPhotoreceptor after 10000th after 50000th 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 0photoreceptor 1Inventive 0 0 0photoreceptor 2Inventive 0 0 0photoreceptor 3Inventive 0 0 0photoreceptor 4Inventive 0 0 2photoreceptor 5Inventive 0 1 0photoreceptor 6Inventive 0 0 0photoreceptor 7Inventive 0 0 1photoreceptor 8Inventive 0 0 0photoreceptor 9Inventive 0 0 1photoreceptor 10Comparative 6 23 31photoreceptor 1Comparative 4 19 37photoreceptor 2______________________________________
TABLE-12______________________________________ Numbers of Numbers of Numbers of white spots white spots white spots produced produced produced afterPhotoreceptor after 10000th after 50000th 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 0photoreceptor 11Inventive 0 0 0photoreceptor 12Inventive 0 0 1photoreceptor 13Inventive 0 0 2photoreceptor 14Inventive 0 1 0photoreceptor 15Inventive 0 0 0photoreceptor 16Inventive 0 0 1photoreceptor 17Inventive 0 1 3photoreceptor 18Inventive 0 0 1photoreceptor 19Inventive 0 0 5photoreceptor 20Comparative 5 27 43photoreceptor 3Comparative 4 25 47photoreceptor 4______________________________________
TABLE-13______________________________________ Numbers of Numbers of Numbers of white spots white spots white spots produced produced produced afterPhotoreceptor after 10000th after 50000th 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 0photoreceptor 21Inventive 0 0 0photoreceptor 22Inventive 0 0 0photoreceptor 23Inventive 0 0 0photoreceptor 24Inventive 0 0 1photoreceptor 25Inventive 0 0 0photoreceptor 26Inventive 0 0 2photoreceptor 27Inventive 0 0 0photoreceptor 28Inventive 0 0 1photoreceptor 29Inventive 0 1 1photoreceptor 30Comparative 3 12 32photoreceptor 5Comparative 4 18 38photoreceptor 6______________________________________
TABLE-14______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 707 103 709 104photoreceptor 31Inventive 702 105 705 106photoreceptor 32Inventive 705 101 707 100photoreceptor 33Inventive 710 96 712 100photoreceptor 34Inventive 708 102 710 105photoreceptor 35Inventive 701 104 703 108photoreceptor 36Inventive 700 106 702 109photoreceptor 37Inventive 698 110 700 107photoreceptor 38Inventive 702 108 705 109photoreceptor 39Inventive 703 106 705 110photoreceptor 40Comparative 697 107 700 152photoreceptor 7Comparative 697 123 685 179photoreceptor 8______________________________________
TABLE-15______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 704 101 705 103photoreceptor 41Inventive 706 106 707 108photoreceptor 42Inventive 708 104 709 109photoreceptor 43Inventive 702 100 704 100photoreceptor 44Inventive 705 102 707 105photoreceptor 45Inventive 710 105 712 108photoreceptor 46Inventive 711 112 713 114photoreceptor 47Inventive 703 109 705 115photoreceptor 48Inventive 704 110 707 113photoreceptor 49Inventive 706 111 708 114photoreceptor 50Comparative 708 120 678 159photoreceptor 9Comparative 717 122 682 175photoreceptor 10______________________________________
TABLE-16______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 705 50 707 51photoreceptor 51Inventive 706 52 706 54photoreceptor 52Inventive 704 48 708 50photoreceptor 53Inventive 703 53 705 53photoreceptor 54Inventive 701 51 702 53photoreceptor 55Inventive 704 51 703 51photoreceptor 56Inventive 705 49 702 50photoreceptor 57Inventive 698 50 704 51photoreceptor 58Inventive 702 54 705 55photoreceptor 59Inventive 701 52 703 55photoreceptor 60Comparative 711 62 685 90photoreceptor 11Comparative 715 59 685 81photoreceptor 12______________________________________
TABLE-17______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 701 102 701 105photoreceptor 61Inventive 702 105 704 106photoreceptor 62Inventive 705 106 706 107photoreceptor 63Inventive 703 104 705 105photoreceptor 64Inventive 704 105 706 106photoreceptor 65Inventive 707 108 708 109photoreceptor 66Inventive 705 109 706 110photoreceptor 67Inventive 702 107 704 108photoreceptor 68Inventive 710 101 710 102photoreceptor 69Inventive 708 105 710 106photoreceptor 70Comparative 716 112 687 155photoreceptor 13Comparative 708 126 683 148photoreceptor 14______________________________________
TABLE-18______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 31Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 32Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 33Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 34Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 35Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 36Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 37Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 38Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 39Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 40Comparative .largecircle. .DELTA. Xphotoreceptor 7Comparative .largecircle. .DELTA. Xphotoreceptor 8______________________________________
TABLE-19______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 41Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 42Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 43Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 44Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 45Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 46Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 47Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 48Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 49Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 50Comparative .largecircle. .DELTA. Xphotoreceptor 9Comparative .largecircle. .DELTA. .DELTA.photoreceptor 10______________________________________
TABLE-20______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 51Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 52Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 53Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 54Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 55Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 56Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 57Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 58Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 59Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 60Comparative .largecircle. .DELTA. Xphotoreceptor 11Comparative .largecircle. .DELTA. Xphotoreceptor 12______________________________________
TABLE-21______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 61Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 62Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 63Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 64Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 65Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 66Inventive .largecircle. .largecircle. .largecircle.photoreceptor 67Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 68Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 69Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 70Comparative .largecircle. .DELTA. Xphotoreceptor 13Comparative .largecircle. .DELTA. Xphotoreceptor 14______________________________________
EXAMPLES 71 THROUGH 105 AND COMPARATIVE EXAMPLES 15 THROUGH 28
Photoreceptors 71 through 105 and comparative photoreceptors 15 through 28 were each prepared in the same manner as in Example 1, except that the CTM used in Example 1 was replaced by the compounds each shown in the following Tables-22 through 28, respectively. The characteristic evaluations thereof were then carried out in the same manners described above, and the results thereof are shown in the following Tables-29 through 42, respectively. It was proved from the results thereof that, as same as in the aforementioned Example 1, the photoreceptivities, residual potentials, image qualities and electric potential stabilities could each be excellent when making use of the CTM of the invention.
TABLE-22______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compound F.sub.1 -23 ExemplifiedExample photoreceptor 71 compound (11)71Inventive Inventive Compound F.sub.1 -23 ExemplifiedExample photoreceptor 72 compound (20)72Inventive Inventive Compound F.sub.1 -1 ExemplifiedExample photoreceptor 73 compound (14)73Inventive Inventive Compound F.sub.1 -1 ExemplifiedExample photoreceptor 74 compound (4)74Inventive Inventive Compound F.sub.1 -6 ExemplifiedExample photoreceptor 75 compound (11)75Compar- Comparative Compound F.sub.1 -23 Comparativeative photoreceptor 15 compound (1)Example15Compar- Comparative Compound F.sub.1 -23 Comparativeative photoreceptor 16 compound (2)Example16______________________________________
TABLE-23______________________________________ PhotoreceptorExample No. No. CGM CTM______________________________________Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 76 photoreceptor 76 compound (1)Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 77 photoreceptor 77 compound (4)Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 78 photoreceptor 78 compound (11)Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 79 photoreceptor 79 compound (13)Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample 80 photoreceptor 80 compound (25)Comparative Comparative Compound Q.sub.1 -3 ComparativeExample 17 photoreceptor 17 compound (1)Comparative Comparative Compound Q.sub.1 -3 ComparativeExample 18 photoreceptor 18 compound (2)______________________________________
TABLE-24______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 81 F.sub.1 -23 compound81 (28)Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 82 F.sub.1 -23 compound82 (11)Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 83 F.sub.1 -23 compound83 (20)Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 84 F.sub.1 -23 compound84 (50)Inventive Inventive Compound Q.sub.1 -3, ExemplifiedExample photoreceptor 85 F.sub.1 -23 compound85 (37)Inventive Inventive Compound Q.sub.1 -3, ExemplifiedCompar- Comparative Compound Q.sub.1 -3, Comparativeative photoreceptor 19 F.sub.1 -23 compound (1)Example19Compar- Comparative Compound Q.sub.1 -3, Comparativeative photoreceptor 20 F.sub.1 -23 compound (2)Example20______________________________________
TABLE-25______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 86 phthalocyanine compound86 (14)Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 87 phthalocyanine compound87 (11)Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 88 phthalocyanine compound88 (17)Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 89 phthalocyanine compound89 (22)Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 90 phthalocyanine compound90 (20)Compar- Comparative .tau. type non-metallic Comparativeative photoreceptor 21 phthalocyanine compound (1)Example21Compar- Comparative .tau. type non-metallic Comparativeative photoreceptor 22 phthalocyanine compound (2)Example22______________________________________
TABLE-26______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 91 phthalocyanine compound91 (42)Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 92 phthalocyanine compound (8)92Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 93 phthalocyanine compound93 (11)Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 94 phthalocyanine compound94 (31)Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 95 phthalocyanine compound95 (20)Compar- Comparative X type non-metallic Comparativeative photoreceptor 23 phthalocyanine compound (1)Example23Compar- Comparative X type non-metallic Comparativeative photoreceptor 24 phthalocyanine compound (2)Example24______________________________________
TABLE-27______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 96 phthalocyanine compound (2)96Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 97 phthalocyanine compound97 (40)Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 98 phthalocyanine compound (5)98Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 99 phthalocyanine compound99 (11)Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 100 phthalocyanine compound100 (14)Compar- Comparative Y type oxytitanium Comparativeative photoreceptor 25 phthalocyanine compound (1)Example25Compar- Comparative Y type oxytitanium Comparativeative photoreceptor 26 phthalocyanine compound (2)Example26______________________________________
TABLE-28______________________________________ PhotoreceptorExample No. No. CGM CTM______________________________________Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 101 photoreceptor 101 compound (6)Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 102 photoreceptor 102 compound (26)Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 103 photoreceptor 103 compound (11)Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample 104 photoreceptor 104 compound (14)Inventive Inventive Compound F.sub.2 -5 ExemplifiedExample 105 photoreceptor 105 compound (60)Comparative Comparative Compound F.sub.2 -6 ComparativeExample 27 photoreceptor 27 compound (1)Comparative Comparative Compound F.sub.2 -6 ComparativeExample 28 photoreceptor 28 compound (2)______________________________________
TABLE-29______________________________________ Vr (v) after 20000th repetition Initial at the following linear velocity white paper Repetition Repetition RepetitionPhotorecep- potential, at 240 at 330 at 440tor No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 51 12 16 20photoreceptor71Inventive 48 10 14 18photoreceptor72Inventive 50 13 15 19photoreceptor73Inventive 74 10 12 17photoreceptor74Inventive 52 13 16 21photoreceptor75Comparative 61 15 38 75photoreceptor15Comparative 73 17 45 89photoreceptor16______________________________________
TABLE-30______________________________________ Vr (v) after 20000th repetition Initial at the following linear velocity white paper Repetition Repetition RepetitionPhotorecep- potential, at 240 at 330 at 440tor No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 97 11 13 22photoreceptor76Inventive 99 10 14 23photoreceptor77Inventive 94 9 11 21photoreceptor78Inventive 100 12 15 25photoreceptor79Inventive 102 10 13 24photoreceptor80Comparative 112 14 37 75photoreceptor17Comparative 121 15 39 79photoreceptor18______________________________________
TABLE-31______________________________________ Vr (v) after 20000th repetition Initial at the following linear velocity white paper Repetition Repetition RepetitionPhotorecep- potential, at 240 at 330 at 440tor No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 63 10 14 22photoreceptor81Inventive 70 13 15 25photoreceptor82Inventive 65 9 13 19photoreceptor83Inventive 69 15 18 26photoreceptor84Inventive 71 14 19 27photoreceptor85Comparative 80 17 45 85photoreceptor19Comparative 95 18 37 84photoreceptor20______________________________________
TABLE-32______________________________________ Numbers of Numbers of Numbers of white spots white spots white spots produced produced produced afterPhotoreceptor after 10000th after 50000th 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 1photoreceptor 71Inventive 0 0 0photoreceptor 72Inventive 0 0 0photoreceptor 73Inventive 0 1 1photoreceptor 74Inventive 0 0 1photoreceptor 75Comparative 6 23 31photoreceptor 15Comparative 4 19 37photoreceptor 16______________________________________
TABLE-33______________________________________ Numbers of Numbers of Numbers of white spots white spots white spots produced produced produced afterPhotoreceptor after 10000th after 50000th 100000thNo. repetition repetition repetition______________________________________Inventive 0 1 1photoreceptor 76Inventive 0 1 1photoreceptor 77Inventive 0 0 0photoreceptor 78Inventive 0 0 1photoreceptor 79Inventive 0 0 2photoreceptor 80Comparative 5 27 43photoreceptor 17Comparative 4 25 47photoreceptor 18______________________________________
TABLE-34______________________________________ Numbers of Numbers of Numbers of white spots white spots white spots produced produced produced afterPhotoreceptor after 10000th after 50000th 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 0photoreceptor 81Inventive 0 0 1photoreceptor 82Inventive 0 0 0photoreceptor 83Inventive 0 0 0photoreceptor 84Inventive 0 1 0photoreceptor 85Comparative 3 12 32photoreceptor 19Comparative 2 18 38photoreceptor 20______________________________________
TABLE-35______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 712 97 716 101photoreceptor 86Inventive 705 96 711 108photoreceptor 87Inventive 698 103 702 105photoreceptor 88Inventive 703 101 700 103photoreceptor 89Inventive 708 104 712 107photoreceptor 90Comparative 697 107 700 152photoreceptor 21Comparative 697 123 685 179photoreceptor 22______________________________________
TABLE-36______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 698 100 700 99photoreceptor 91Inventive 703 102 704 101photoreceptor 92Inventive 702 104 701 105photoreceptor 93Inventive 708 106 711 107photoreceptor 94Inventive 699 98 702 103photoreceptor 95Comparative 708 120 678 159photoreceptor 23Comparative 717 122 682 175photoreceptor 24______________________________________
TABLE-37______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 702 51 706 53photoreceptor 96Inventive 708 52 709 55photoreceptor 97Inventive 705 51 707 53photoreceptor 98Inventive 711 55 713 56photoreceptor 99Inventive 698 49 701 50photoreceptor 100Comparative 711 62 685 90photoreceptor 25Comparative 715 59 685 81photoreceptor 26______________________________________
TABLE-38______________________________________ Ordinary temperature Low temperaturePhotoreceptor (25.degree. C.) (10.degree. C.)No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 702 99 701 103photoreceptor 101Inventive 708 109 710 103photoreceptor 102Inventive 704 108 702 102photoreceptor 103Inventive 706 106 705 104photoreceptor 104Inventive 712 100 713 101photoreceptor 105Comparative 716 112 687 155photoreceptor 27Comparative 708 126 683 148photoreceptor 28______________________________________
TABLE-39______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 86Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 87Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 88Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 89Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 90Comparative .largecircle. .DELTA. Xphotoreceptor 21Comparative .largecircle. .DELTA. Xphotoreceptor 22______________________________________
TABLE-40______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 91Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 92Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 93Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 94Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 95Comparative .largecircle. .DELTA. Xphotoreceptor 23Comparative .largecircle. .DELTA. .DELTA.photoreceptor 24______________________________________
TABLE-41______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 96Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 97Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 98Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 99Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 100Comparative .largecircle. .DELTA. Xphotoreceptor 25Comparative .largecircle. .DELTA. Xphotoreceptor 26______________________________________
TABLE-42______________________________________ Black spot Black spot judgement judgement Black spot made after made judgement madePhotoreceptor 20000th after 50000th after 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 101Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 102Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 103Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 104Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 105Comparative .largecircle. .DELTA. Xphotoreceptor 27Comparative .largecircle. .DELTA. Xphotoreceptor 28______________________________________
EXAMPLES 106-175 and COMPARATIVE EXAMPLES 29-42
Photoreceptors 106 through 175 and comparative photoreceptors 29 through 42 were each prepared in the same manner as in Example 1, except that the CGM and CTM used in Example 1 were each replaced by the compounds each shown in the following Tables-43 through 49, respectively. The characteristic evaluations thereof were then carried out in the same manners described above, and the results thereof are shown in the following Tables-50 through 63, respectively. It was proved from the results thereof that, as same as in the aforementioned Example 1, the photoreceptivities, residual potentials, image qualities and electric potential stabilities could each be excellent when making use of the CTM of the invention.
TABLE-43______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compounds F.sub.1 -23 ExemplifiedExample photoreceptor 106 compounds [3]106Inventive Inventive Compounds F.sub.1 -23 ExemplifiedExample photoreceptor 107 compounds [12]107Inventive Inventive Compounds F.sub.1 -23 ExemplifiedExample photoreceptor 108 compounds [21]108Inventive Inventive Compounds F.sub.1 -23 ExemplifiedExample photoreceptor 109 compounds [29]109Inventive Inventive Compounds F.sub.1 -23 ExemplifiedExample photoreceptor 110 compounds [37]110Inventive Inventive Compounds F.sub.1 -1 ExemplifiedExample photoreceptor 111 compounds [53]111Inventive Inventive Compounds F.sub.1 -1 ExemplifiedExample photoreceptor 112 compounds [56]112Inventive Inventive Compounds F.sub.1 -1 ExemplifiedExample photoreceptor 113 compounds [66]113Inventive Inventive Compounds F.sub.1 -7 ExemplifiedExample photoreceptor 114 compounds [78]114Inventive Inventive Compounds F.sub.1 -6 ExemplifiedExample photoreceptor 115 compounds115 [150]Compar- Comparative Compound F.sub.1 -23 Comparativeative photoreceptor 29 compound (3)Example29Compar- Comparative Compound F.sub. 1 -23 Comparativeative photoreceptor 30 compound (2)Example30______________________________________ *Comparative Example (3) is shown later.
TABLE-44______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 116 compounds [1]116Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 117 compounds [21]117Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 118 compounds [33]118Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 119 compounds [45]119Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 120 compounds [48]120Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 121 compounds [57]121Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 122 compounds [65]122Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 123 compounds [87]123Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 124 compounds [93]124Inventive Inventive Compound Q.sub.1 -3 ExemplifiedExample photoreceptor 125 compounds [150]125Compar- Comparative Compound Q.sub.1 -3 Comparativeative photoreceptor 31 compound (3)Example31Compar- Comparative Compound Q.sub.1 -3 Comparativeative photoreceptor 32 compound (2)Example32______________________________________
TABLE-45______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 126 F.sub.1 -23 compound126 [21]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 127 F.sub.1 -23 compound127 [39]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 128 F.sub.1 -23 compound128 [48]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 129 F.sub.1 -23 compound129 [66]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 130 F.sub.1 -23 compound130 [73]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 131 F.sub.1 -23 compound131 [92]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 132 F.sub.1 -23 compound132 [100]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 133 F.sub.1 -23 compound133 [114]Inventive Inventive Compounds Q.sub. 1 -3, ExemplifiedExample photoreceptor 134 F.sub.1 -23 compound134 [120]Inventive Inventive Compounds Q.sub.1 -3, ExemplifiedExample photoreceptor 135 F.sub.1 -23 compound135 [155]Compar- Comparative Compound Q.sub.1 -3, Comparativeative photoreceptor 33 F.sub.1 -23 compound (3)Example33Compar- Comparative Compound Q.sub.1 -3, Comparativeative photoreceptor 34 F.sub.1 -23 compound (2)Example34______________________________________
TABLE-46______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 136 phthalocyanine compound [2]136Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 137 phthalocyanine compound137 [21]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 138 phthalocyanine compound138 [37]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 139 phthalocyanine compound139 [43]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 140 phthalocyanine compound140 [47]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 141 phthalocyanine compound141 [57]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 142 phthalocyanine compound142 [70]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 143 phthalocyanine compound143 [75]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 144 phthalocyanine compound144 [102]Inventive Inventive .tau. type non-metallic ExemplifiedExample photoreceptor 145 phthalocyanine compound145 [150]Compar- Comparative .tau. type non-metallic Comparativeative photoreceptor 35 phthalocyanine compound (3)Example35Compar- Comparative .tau. type non-metallic Comparativeative photoreceptor 36 phthalocyanine compound (2)Example36______________________________________
TABLE-47______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 146 phthalocyanine compound [6]146Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 147 phthalocyanine compound147 [12]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 148 phthalocyanine compound148 [21]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 149 phthalocyanine compound149 [38]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 150 phthalocyanine compound150 [47]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 151 phthalocyanine compound151 [55]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 152 phthalocyanine compound152 [72]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 153 phthalocyanine compound153 [79]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 154 phthalocyanine compound154 [88]Inventive Inventive X type non-metallic ExemplifiedExample photoreceptor 155 phthalocyanine compound155 [104]Compar- Comparative X type non-metallic Comparativeative photoreceptor 37 phthalocyanine compound (3)Example37Compar- Comparative X type non-metallic Comparativeative photoreceptor 38 phthalocyanine compound (2)Example38______________________________________
______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 156 phthalocyanine compound [3]156Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 157 phthalocyanine compound157 [12]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 158 phthalocyanine compound158 [26]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 159 phthalocyanine compound159 [50]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 160 phthalocyanine compound160 [71]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 161 phthalocyanine compound161 [73]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 162 phthalocyanine compound162 [93]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 163 phthalocyanine compound163 [103]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 164 phthalocyanine compound164 [116]Inventive Inventive Y type oxytitanium ExemplifiedExample photoreceptor 165 phthalocyanine compound165 [150]Compar- Comparative Y type oxytitanium Comparativeative photoreceptor 39 phthalocyanine compound (3)Example39Compar- Comparative Y type oxytitanium Comparativeative photoreceptor 40 phthalocyanine compound (2)Example40______________________________________
TABLE-49______________________________________Example PhotoreceptorNo. No. CGM CTM______________________________________Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 166 compound [3]166Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 167 compound [12]167Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 168 compound [21]168Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 169 compound [30]169Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 170 compound [39]170Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 171 compound [48]171Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 172 compound [57]172Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 173 compound [60]173Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 174 compound [75]174Inventive Inventive Compound F.sub.2 -6 ExemplifiedExample photoreceptor 175 compound [84]175Compar- Comparative Compound F.sub.2 -6 Comparativeative photoreceptor 41 compound (3)Example41Compar- Comparative Compound F.sub.2 -6 Comparativeative photoreceptor 42 compound (2)Example42______________________________________
TABLE-50______________________________________ Vr (v) after 20000th repetition Initial at the following linear velocity white paper Repetition Repetition RepetitionPhotorecep- potential, at 240 at 330 at 440tor No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 46 10 13 19photoreceptor106Inventive 48 13 15 22photoreceptor107Inventive 51 12 15 23photoreceptor108Inventive 53 13 16 23photoreceptor109Inventive 48 11 14 21photoreceptor110Inventive 49 8 13 21photoreceptor111Inventive 47 10 15 23photoreceptor112Inventive 54 10 15 22photoreceptor113Inventive 50 14 17 26photoreceptor114Inventive 50 15 18 27photoreceptor115Comparative 67 14 40 76photoreceptor29Comparative 73 17 45 89photoreceptor30______________________________________
TABLE-51______________________________________ Vr (v) after 20000th repetition Initial at the following linear velocity white paper Repetition Repetition RepetitionPhotorecep- potential, at 240 at 330 at 440tor No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 102 11 15 25photoreceptor116Inventive 100 12 15 23photoreceptor117Inventive 97 15 18 26photoreceptor118Inventive 103 11 14 22photoreceptor119Inventive 97 12 16 23photoreceptor120Inventive 96 9 13 21photoreceptor121Inventive 107 13 18 27photoreceptor122Inventive 95 10 13 21photoreceptor123Inventive 101 9 12 22photoreceptor124Inventive 104 10 14 24photoreceptor125Comparative 118 13 40 78photoreceptor31Comparative 121 15 39 79photoreceptor32______________________________________
TABLE-52______________________________________ Vr (v) after 20000th repetition Initial at the following linear velocity white paper Repetition Repetition RepetitionPhotorecep- potential, at 240 at 330 at 440tor No. Vw (v) mm/sec. mm/sec. mm/sec.______________________________________Inventive 63 13 18 25photoreceptor126Inventive 73 12 16 24photoreceptor127Inventive 68 10 15 22photoreceptor128Inventive 66 9 15 24photoreceptor129Inventive 73 9 14 22photoreceptor130Inventive 71 11 15 22photoreceptor131Inventive 70 12 17 25photoreceptor132Inventive 67 12 18 26photoreceptor133Inventive 69 15 20 29photoreceptor134Inventive 73 14 21 29photoreceptor135Comparative 88 18 40 77photoreceptor33Comparative 95 18 39 84photoreceptor34______________________________________
TABLE-53______________________________________ Numbers of Numbers of Numbers of white white white spot produced spot produced spot producedPhotoreceptor after 10000th after 50000th after 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 0photoreceptor 106Inventive 0 1 1photoreceptor 107Inventive 0 1 2photoreceptor 108Inventive 0 0 0photoreceptor 109Inventive 0 0 1photoreceptor 110Inventive 0 0 0photoreceptor 111Inventive 0 1 1photoreceptor 112Inventive 0 0 0photoreceptor 113Inventive 0 1 2photoreceptor 114Inventive 0 1 1photoreceptor 115Comparative 4 24 40photoreceptor 29Comparative 4 19 37photoreceptor 30______________________________________
TABLE-54______________________________________ Numbers of Numbers of Numbers of white white white spot produced spot produced spot producedPhotoreceptor after 10000th after 50000th after 100000thNo. repetition repetition repetition______________________________________Inventive 0 0 1photoreceptor 116Inventive 0 0 2photoreceptor 117Inventive 0 0 0photoreceptor 118Inventive 0 0 0photoreceptor 119Inventive 0 0 1photoreceptor 120Inventive 0 0 0photoreceptor 121Inventive 0 0 1photoreceptor 122Inventive 0 1 2photoreceptor 123Inventive 0 0 0photoreceptor 124Inventive 0 1 3photoreceptor 125Comparative 7 22 50photoreceptor 31Comparative 4 25 47photoreceptor 32______________________________________
TABLE-55______________________________________ Numbers of Numbers of Numbers of white white white spot produced spot produced spot producedPhotoreceptor after 10000th after 50000th after 100000thNo. repetition repetition repetition______________________________________Inventive 0 1 2photoreceptor 126Inventive 0 1 2photoreceptor 127Inventive 0 0 0photoreceptor 128Inventive 0 1 1photoreceptor 129Inventive 0 0 1photoreceptor 130Inventive 0 1 1photoreceptor 131Inventive 0 1 2photoreceptor 132Inventive 0 0 0photoreceptor 133Inventive 0 0 3photoreceptor 134Inventive 0 1 2photoreceptor 135Comparative 5 22 44photoreceptor 33Comparative 2 18 38photoreceptor 34______________________________________
TABLE-56______________________________________ Ordinary temperature Low temperature (25.degree. C.) (10.degree. C.)Photoreceptor No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 710 101 711 101photoreceptor 135Inventive 705 102 709 103photoreceptor 137Inventive 697 99 699 102photoreceptor 138Inventive 698 104 700 104photoreceptor 139Inventive 693 105 697 107photoreceptor 140Inventive 701 110 705 113photoreceptor 141Inventive 705 113 706 114photoreceptor 142Inventive 699 100 703 102photoreceptor 143Inventive 700 98 704 99photoreceptor 144Inventive 712 109 714 110photoreceptor 145Comparative 690 120 677 165photoreceptor 35Comparative 697 123 685 179photoreceptor 36______________________________________
TABLE-57______________________________________ Ordinary temperature Low temperature (25.degree. C.) (10.degree. C.)Photoreceptor No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 721 95 719 98photoreceptor 145Inventive 710 94 706 97photoreceptor 147Inventive 725 105 721 107photoreceptor 148Inventive 701 103 700 105photoreceptor 149Inventive 705 92 700 95photoreceptor 150Inventive 708 90 704 94photoreceptor 151Inventive 718 105 710 109photoreceptor 152Inventive 710 108 708 109photoreceptor 153Inventive 724 107 720 110photoreceptor 154Inventive 715 102 713 104photoreceptor 155Comparative 712 125 678 174photoreceptor 37Comparative 717 122 682 175photoreceptor 38______________________________________
TABLE-58______________________________________ Ordinary temperature Low temperature (25.degree. C.) (10.degree. C.)Photoreceptor No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 712 50 715 51photoreceptor 156Inventive 714 53 717 54photoreceptor 157Inventive 718 54 721 56photoreceptor 158Inventive 704 51 707 53photoreceptor 159Inventive 720 55 722 57photoreceptor 160Inventive 706 49 710 50photoreceptor 161Inventive 701 47 704 49photoreceptor 162Inventive 708 50 710 51photoreceptor 163Inventive 712 51 713 52photoreceptor 164Inventive 719 55 723 57photoreceptor 165Comparative 718 57 690 88photoreceptor 39Comparative 715 59 685 81photoreceptor 40______________________________________
TABLE-59______________________________________ Ordinary temperature Low temperature (25.degree. C.) (10.degree. C.)Photoreceptor No. VH (v) VL (v) VH (v) VL (v)______________________________________Inventive 718 108 717 110photoreceptor 166Inventive 701 104 702 108photoreceptor 167Inventive 708 110 709 112photoreceptor 168Inventive 710 100 710 104photoreceptor 169Inventive 711 98 710 100photoreceptor 170Inventive 716 101 715 105photoreceptor 171Inventive 702 105 702 107photoreceptor 172Inventive 707 97 706 100photoreceptor 173Inventive 710 95 711 99photoreceptor 174Inventive 715 103 714 106photoreceptor 175Comparative 701 118 671 150photoreceptor 41Comparative 708 126 683 148photoreceptor 42______________________________________
TABLE-60______________________________________ Black spot Black spot Black spot judgement judgement judgement made after made after made afterPhotoreceptor 20000th 50000th 100000thused copies copies copies______________________________________Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 136Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 137Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 138Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 139Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 140Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 141Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 142Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 143Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 144Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 145Comparative .largecircle. .DELTA. Xphotoreceptor 35Comparative .largecircle. .DELTA. Xphotoreceptor 36______________________________________
TABLE-61______________________________________ Black spot Black spot Black spot judgement judgement judgement made after made after made afterPhotoreceptor 20000th 50000th 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 146Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 147Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 148Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 149Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 150Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 151Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 152Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 153Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 154Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 155Comparative .largecircle. .DELTA. Xphotoreceptor 37Comparative .largecircle. .DELTA. .DELTA.photoreceptor 38______________________________________
TABLE-62______________________________________ Black spot Black spot Black spot judgement judgement judgement made after made after made afterPhotoreceptor 20000th 50000th 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 156Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 157Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 158Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 159Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 160Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 161Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 162Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 163Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 164Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 165Comparative .largecircle. .DELTA. .DELTA.photoreceptor 39Comparative .largecircle. .DELTA. Xphotoreceptor 40______________________________________
TABLE-63______________________________________ Black spot Black spot Black spot judgement judgement judgement made after made after made afterPhotoreceptor 20000th 50000th 100000thused copies copies copies______________________________________Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 166Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 167Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 168Inventive .circleincircle. .circleincircle. .largecircle.photoreceptor 169Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 170Inventive .circleincircle. .largecircle. .largecircle.photoreceptor 171Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 172Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 173Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 174Inventive .circleincircle. .circleincircle. .circleincircle.photoreceptor 175Comparative .largecircle. .DELTA. Xphotoreceptor 41Comparative .largecircle. .DELTA. Xphotoreceptor 42______________________________________
As described above, when any electrophotographic photoreceptor relating to the invention is incorporated into a copier or printer and is then used repeatedly, every highly photoreceptive and excellent image can be provided without producing any image defect or image failure such as white-dots, black-dots, fog and density lowering.
Even when any electrophotographic photoreceptor relating to the invention is incorporated into a copier or printer and then used repeatedly, every excellent image can be provided with a reduced residual potential and without producing any image defect and image failure.
EXAMPLE 176
Next, an example different from the above-given examples, in which the invention was applied to an electroluminescence (EL), will be detailed.
Over to a transparent electrode (that was a layer made of indium and tin oxide) formed on a glass-made substrate, Exemplified Compound No.6 was so vacuum-evaporated as to serve as the electric charge injecting layer so that the thickness thereof could be 500 .ang.. Next, an 8-quinolinol A1 complex (A1q.sub.3) was vacuum-evaporated so as to serve as the organic fluorescent layer so that the thickness thereof could be 600 .ang.. Further, a magnesium/silver alloy was vacuum-evaporated thereon so as to serve as the negative electrode thereof.
When checking up the light emitting characteristics of the resulting thin organic EL element, a light emission of 0.04 mW/cm.sup.2 could be obtained at 4 mA/cm.sup.2. The emitted light was in yellowish green.
EXAMPLE 177
A thin organic EL element was prepared in the same manner as in Example 176, except that the electric-charge injecting layer used in Example 176 was replaced by Exemplified Compound No. (14) having 500 .ang. so as to serve as the electric-charge injecting layer thereof, (provided, therein the negative electrode was made of a magnesium/aluminium alloy). When checking up the resulting light emitting characteristics thereof, the resulting light emission of 0.05 mW/cm.sup.2 could be obtained at 5 mA/cm.sup.2. The emitted light was in yellowish green.
EXAMPLE 178
A thin organic EL element was prepared in the same manner as in Example 176, except that the electric-charge injecting layer used in Example 176 was replaced by Exemplified Compound No. [21] having 500 .ang. so as to serve as the electric-charge injecting layer thereof, (provided, therein the negative electrode was made of a magnesium/aluminium alloy). When checking up the resulting light emitting characteristics thereof, the resulting light emission of 0.06 mW/cm.sup.2 could be obtained at 6 mA/cm.sup.2. The emitted light was in yellowish green.
Examples of Compounds having Formula [I]
______________________________________ ##STR16##No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 R.sup.5' R.sup.6' R.sup.7'______________________________________1 CH.sub.3 H H H CH.sub.3 H H H H H2 CH.sub.3 H H H H CH.sub.3 H H H H3 CH.sub.3 H H H H H CH.sub.3 H H H4 H CH.sub.3 H H CH.sub.3 H H H H H5 H CH.sub.3 H H H CH.sub.3 H H H H6 H CH.sub.3 H H H H CH.sub.3 H H H7 H H CH.sub.3 H CH.sub.3 H H H H H8 H H CH.sub.3 H H CH.sub.3 H H H H9 H H CH.sub.3 H H H CH.sub.3 H H H10 H H H CH.sub.3 CH.sub.3 H H H H H11 H H H CH.sub.3 H CH.sub.3 H H H H12 H H H CH.sub.3 H H CH.sub.3 H H H______________________________________
Examples of Compounds having Formula [I]
______________________________________ ##STR17##No. R.sup.1 -R.sup.4 R.sup.5 -R.sup.9 R.sup.5' -R.sup.9'______________________________________13 3-CH.sub.3 2-C.sub.2 H.sub.5 H14 3-CH.sub.3 3-C.sub.2 H.sub.5 H15 3-CH.sub.3 4-C.sub.2 H.sub.5 H16 3-CH.sub.3 4-C.sub.2 H.sub.5 4-C.sub.2 H.sub.517 3-CH.sub.3 2-F H18 3-CH.sub.3 3-F H19 3-CH.sub.3 4-F H20 3-CH.sub.3 2-Cl 2, 4-di-CH.sub. 321 3-CH.sub.3 4-Cl H22 3-CH.sub.3 3-Br H23 3-CH.sub.3 4-I H24 3-CH.sub.3 4-CF.sub.3 H25 3-CH.sub.3 4-CN H26 3-CH.sub.3 4-CH.sub.2 COOCH.sub.3 H27 3-CH.sub.3 3-OCOC.sub.2 H.sub.5 H28 3-CH.sub.3 3-C.sub.2 H.sub.5 4-C.sub.2 H.sub.529 3-CH.sub.3 2-CH.sub.3, 4-Cl H30 3-CH.sub.3 ##STR18## H31 3-CH.sub.3 4-OCH.sub.3 H32 3-CH.sub.3 4-OCH.sub.3 4-OCH.sub.333 3-CH.sub.3 4-OC.sub.2 H.sub.5 H______________________________________
Examples of Compounds having Formula [I]
______________________________________ ##STR19##No. R.sup.1 -R.sup.4 R.sup.5 -R.sup.9 R.sup.5' -R.sup.9'______________________________________34 4-CH.sub.3 4-OCH.sub.3 H35 4-CH.sub.3 4-OCH.sub.3 4-OCH.sub.336 4-CH.sub.3 4-OCH.sub.3 4-CH.sub.337 4-CH.sub.3 4-Cl H38 4-CH.sub.3 3-Br H39 4-CH.sub.3 2-CN H40 4-CH.sub.3 3-C.sub.2 H.sub.4 COOCH.sub.3 H41 4-CH.sub.3 3-CF.sub.3 H42 4-CH.sub.3 ##STR20## H43 4-CH.sub.3 ##STR21## H44 4-CH.sub.3 ##STR22## H45 4-CH.sub.3 4-Cl 4-Cl46 4-CH.sub.3 2,3,4,5,6-per-F H47 4-CH.sub.3 2,4-di-Cl H48 4-CH.sub.3 4-C.sub.2 H.sub.5 4-C.sub.2 H.sub.549 4-CH.sub.3 3,4,5-tri-OCH.sub.3 H50 4-CH.sub.3 4-OH H51 4-CH.sub.3 2,4-di-OCH.sub.3 H52 4-CH.sub.3 4-Cl 3-Br53 4-CH.sub.3 4-CH.sub.3 3-Cl54 4-CH.sub.3 2,4-di-CH.sub.3 4-OCH.sub.3______________________________________
Examples of Compounds having Formula [I]
______________________________________ ##STR23##No. R.sup.1 -R.sup.4 R.sup.5 -R.sup.9 R.sup.5' -R.sup.9'______________________________________55 5-CH.sub.3 4-OCH.sub.3 H56 5-CH.sub.3 4-OCH.sub.3 4-OCH.sub.357 5-CH.sub.3 4-Cl H58 5-CH.sub.3 3-Cl H59 5-CH.sub.3 2-Cl H60 5-CH.sub.3 4-Cl 4-Cl61 5-CH.sub.3 ##STR24## H62 5-CH.sub.3 4-CF.sub. 3 H63 5-CH.sub.3 4-CN H64 5-CH.sub.3 ##STR25## H65 5-CH.sub.3 2,4-di-Cl H66 6-CH.sub.3 4-OCH.sub.3 H67 6-CH.sub.3 4-OCH.sub.3 4-OCH.sub.368 6-CH.sub.3 4-Cl H69 6-CH.sub.3 3-Br H70 6-CH.sub.3 4-I 4-CH.sub.371 6-CH.sub.3 2,4-di-F H72 6-CH.sub.3 2-CH.sub.3 4-Cl73 6-CH.sub.3 2-CN 4-CN74 6-CH.sub.3 ##STR26## H75 6-CH.sub.3 ##STR27## H______________________________________
Examples of Compounds having Formula [I] ##STR28##
Examples of Compounds having Formula [I] ##STR29##
Examples of Compounds having Formula [I] ##STR30##
Synthesis Example: Synthesis of Exemplified Compound No. 6 ##STR31##
Examples of Compounds having Formula [II]
__________________________________________________________________________ ##STR32##CompoundNo. R.sup.a R.sup.b R.sup.c__________________________________________________________________________ (1) 3rd positioned CH.sub.3, 1-6th positioned H 1-6th positioned H 4-5th positioned H (2) 3rd positioned CH.sub.3, 1-6th positioned H 2nd positioned CH.sub.3, 4-5th positioned H the other positioned Hs (3) 3rd positioned CH.sub.3, 1-6th positioned H 3rd positioned CH.sub.3, 4-5th positioned H the other positioned Hs (4) 3rd positioned CH.sub.3, 1-6th positioned H 4th positioned CH.sub.3, 4-5th positioned H the other positioned Hs (5) 3rd positioned CH.sub.3, 2nd positioned CH.sub.3, 2nd positioned CH.sub.3, 4-5th positioned H the other positioned Hs the other positioned Hs (6) 3rd positioned CH.sub.3, 2nd positioned CH.sub.3, 3rd positioned CH.sub.3, 4-5th positioned H the other positioned Hs the other positioned Hs (7) 3rd positioned CH.sub.3, 2nd positioned CH.sub.3, 4th positioned CH.sub.3, 4-5th positioned H the other positioned Hs the other positioned Hs (8) 3rd positioned CH.sub.3, 3rd positioned CH.sub.3, 3rd positioned CH.sub.3, 4-5th positioned H the other positioned Hs the other positioned Hs (9) 3rd positioned CH.sub.3, 3rd positioned CH.sub.3, 4th positioned CH.sub.3, 4-5th positioned H the other positioned Hs the other positioned Hs(10) 3rd positioned CH.sub.3, 4th positioned CH.sub.3, 4th positioned CH.sub.3, 4-5th positioned H the other positioned Hs the other positioned Hs(11) 4th positioned CH.sub.3, 1-6th positioned H 1-6th positioned H 3-5th positioned H(12) 4th positioned CH.sub.3, 1-6th positioned H 2nd positioned CH.sub.3, 3-5th positioned H the other positioned Hs(13) 4th positioned CH.sub.3, 1-6th positioned H 3rd positioned CH.sub.3, 3-5th positioned H the other positioned Hs(14) 4th positioned CH.sub.3, 1-6th positioned H 4th positioned CH.sub.3, 3-5th positioned H the other positioned Hs(15) 4th positioned CH.sub.3, 2nd positioned CH.sub.3, 2nd positioned CH.sub.3, 3-5th positioned H the other positioned Hs the other positioned Hs(16) 4th positioned CH.sub.3, 2nd positioned CH.sub.3, 3rd positioned CH.sub.3, 3-5th positioned H the other positioned Hs the other positioned Hs(17) 4th positioned CH.sub.3, 2nd positioned CH.sub.3, 4th positioned CH.sub.3, 3-5th positioned H the other positioned Hs the other positioned Hs(18) 4th positioned CH.sub.3, 3rd positioned CH.sub.3, 3rd positioned CH.sub.3, 3-5th positioned H the other positioned Hs the other positioned Hs(19) 4th positioned CH.sub.3, 3rd positioned CH.sub.3, 4th positioned CH.sub.3, 3-5th positioned H the other positioned Hs the other positioned Hs(20) 4th positioned CH.sub.3, 4th positioned CH.sub.3, 4th positioned CH.sub.3, 3-5th positioned H the other positioned Hs the other positioned Hs__________________________________________________________________________
Examples of Compounds having Formula [II] ##STR33##
Examples of Compounds having Formula [II] ##STR34##
Examples of Compounds having Formula [II]
______________________________________ ##STR35##No. R.sup.1 -R.sup.3 R.sup.4 -R.sup.8 R.sup.4' -R.sup.8'______________________________________(29) 3-CH.sub.3 4-C.sub.2 H.sub.5 H(30) 3-CH.sub.3 5-C.sub.2 H.sub.5 H(31) 3-CH.sub.3 6-C.sub.2 H.sub.5 H(32) 3-CH.sub.3 6-C.sub.2 H.sub.5 6'-C.sub.2 H.sub.5(33) 3-CH.sub.3 4-F H(34) 3-CH.sub.3 5-F H(35) 3-CH.sub.3 6-F H(36) 3-CH.sub.3 4-Cl 4' ,6'-di-CH.sub.3(37) 3-CH.sub.3 6-Cl H(38) 3-CH.sub.3 5-Br H(39) 3-CH.sub.3 6-I H(40) 3-CH.sub.3 6-CF.sub.3 H(41) 3-CH.sub.3 6-CN H(42) 3-CH.sub.3 6-CH.sub.2 COOCH.sub.3 H(43) 3-CH.sub.3 5-OCOC.sub.2 H.sub.5 H(44) 3-CH.sub.3 5,6-di-CH.sub.3 H(45) 3-CH.sub.3 4-CH.sub.3,6-Cl H(46) 3-CH.sub.3 ##STR36## H(47) 3-CH.sub.3 6-OCH.sub.3 H(48) 3-CH.sub.3 6-OCH.sub.3 6'-OCH.sub.3(49) 3-CH.sub.3 6-OC.sub.2 H.sub.5 H______________________________________
Examples of Compounds having Formula [II]
______________________________________ ##STR37##No. R.sup.1 -R.sup.3 R.sup.4 -R.sup.8 R.sup.4' -R.sup.8'______________________________________(50) 4-CH.sub.3 6-OCH.sub.3 H(51) 4-CH.sub.3 6-OCH.sub.3 6'-OCH.sub.3(52) 4-CH.sub.3 6-OCH.sub.3 6'-CH.sub.3(53) 4-CH.sub.3 6-Cl H(54) 4-CH.sub.3 5-Br H(55) 4-CH.sub.3 4-CN H(56) 4-CH.sub.3 5-C.sub.2 H.sub.4 COOCH.sub.3 H(57) 4-CH.sub.3 5-CF.sub.3 H(58) 4-CH.sub. 3 ##STR38## H(59) 4-CH.sub.3 ##STR39## H(60) 4-CH.sub.3 ##STR40## H(61) 4-CH.sub.3 6-Cl 6'-Cl(62) 4-CH.sub.3 4,5,6,7,8-per-F H(63) 4-CH.sub.3 4,6-di-Cl H(64) 4-CH.sub.3 6-C.sub.2 H.sub.5 6'-C.sub.2 H.sub.5(65) 4-CH.sub.3 5,6,7-tri-OCH.sub.3 H(66) 4-CH.sub.3 6-OH H(67) 4-CH.sub.3 4,6-di-OCH.sub.3 H(68) 4-CH.sub.3 6-Cl 5'-Br(69) 4-CH.sub.3 6-CH.sub.3 5'-Cl(70) 4-CH.sub.3 4,6-di-CH.sub.3 6'-OCH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR41##CompoundNo. R.sup.1 R R'______________________________________ [1] OC.sub.2 H.sub.5 o-CH.sub.3 H [2] OC.sub.2 H.sub.5 m-CH.sub.3 H [3] OC.sub.2 H.sub.5 p-CH.sub.3 H [4] OC.sub.2 H.sub.5 o-CH.sub.3 o-CH.sub.3 [5] OC.sub.2 H.sub.5 m-CH.sub.3 m-CH.sub.3 [6] OC.sub.2 H.sub.5 p-CH.sub.3 p-CH.sub.3 [7] OC.sub.2 H.sub.5 o-CH.sub.3 m-CH.sub.3 [8] OC.sub.2 H.sub.5 o-CH.sub.3 p-CH.sub.3 [9] OC.sub.2 H.sub.5 m-CH.sub.3 p-CH.sub.3[10] m-C.sub.2 H.sub.5 o-CH.sub.3 H[11] m-C.sub.2 H.sub.5 m-CH.sub.3 H[12] m-C.sub.2 H.sub.5 p-CH.sub.3 H[13] m-C.sub.2 H.sub.5 o-CH.sub.3 o-CH.sub.3[14] m-C.sub.2 H.sub.5 m-CH.sub.3 m-CH.sub.3[15] m-C.sub.2 H.sub.5 p-CH.sub.3 p-CH.sub.3[16] m-C.sub.2 H.sub.5 o-CH.sub.3 m-CH.sub.3[17] m-C.sub.2 H.sub.5 o-CH.sub.3 p-CH.sub.3[18] m-C.sub.2 H.sub.5 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR42##CompoundNo. R.sup.1 R R'______________________________________[19] PC.sub.2 H.sub.5 o-CH.sub.3 H[20] PC.sub.2 H.sub.5 m-CH.sub.3 H[21] PC.sub.2 H.sub.5 p-CH.sub.3 H[22] PC.sub.2 H.sub.5 o-CH.sub.3 o-CH.sub.3[23] PC.sub.2 H.sub.5 m-CH.sub.3 m-CH.sub.3[24] PC.sub.2 H.sub.5 p-CH.sub.3 p-CH.sub.3[25] PC.sub.2 H.sub.5 o-CH.sub.3 m-CH.sub.3[26] PC.sub.2 H.sub.5 o-CH.sub.3 p-CH.sub.3[27] PC.sub.2 H.sub.5 m-CH.sub.3 p-CH.sub.3[28] o-n-C.sub.3 H.sub.7 o-CH.sub.3 H[29] o-n-C.sub.3 H.sub.7 m-CH.sub. 3 H[30] o-n-C.sub.3 H.sub.7 p-CH.sub.3 H[31] o-n-C.sub.3 H.sub.7 o-CH.sub.3 o-CH.sub.3[32] o-n-C.sub.3 H.sub.7 m-CH.sub.3 m-CH.sub.3[33] o-n-C.sub.3 H.sub.7 p-CH.sub.3 p-CH.sub.3[34] o-n-C.sub.3 H.sub.7 o-CH.sub.3 m-CH.sub.3[35] o-n-C.sub.3 H.sub.7 o-CH.sub.3 p-CH.sub.3[36] o-n-C.sub.3 H.sub.7 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR43##CompoundNo. R.sup.1 R R'______________________________________[37] m-C.sub.3 H.sub.7 o-CH.sub.3 H[38] m-C.sub.3 H.sub.7 m-CH.sub.3 H[39] m-C.sub.3 H.sub.7 p-CH.sub.3 H[40] m-C.sub.3 H.sub.7 o-CH.sub.3 o-CH.sub.3[41] m-C.sub.3 H.sub.7 m-CH.sub.3 m-CH.sub.3[42] m-C.sub.3 H.sub.7 p-CH.sub.3 p-CH.sub.3[43] m-C.sub.3 H.sub.7 o-CH.sub.3 m-CH.sub.3[44] m-C.sub.3 H.sub.7 o-CH.sub.3 p-CH.sub.3[45] m-C.sub.3 H.sub.7 m-CH.sub.3 p-CH.sub.3[46] p-C.sub.3 H.sub.7 o-CH.sub.3 H[47] p-C.sub.3 H.sub.7 m-CH.sub.3 H[48] p-C.sub.3 H.sub.7 p-CH.sub.3 H[49] p-C.sub.3 H.sub.7 o-CH.sub.3 o-CH.sub.3[50] p-C.sub.3 H.sub.7 m-CH.sub.3 m-CH.sub.3[51] p-C.sub.3 H.sub.7 p-CH.sub.3 p-CH.sub.3[52] p-C.sub.3 H.sub.7 o-CH.sub.3 m-CH.sub.3[53] p-C.sub.3 H.sub.7 o-CH.sub.3 p-CH.sub.3[54] p-C.sub.3 H.sub.7 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR44##CompoundNo. R.sup.1 R R'______________________________________[55] o-isoC.sub.3 H.sub.7 o-CH.sub.3 H[56] o-isoC.sub.3 H.sub.7 m-CH.sub.3 H[57] o-isoC.sub.3 H.sub.7 p-CH.sub.3 H[58] o-isoC.sub.3 H.sub.7 o-CH.sub.3 o-CH.sub.3[59] o-isoC.sub.3 H.sub.7 m-CH.sub.3 m-CH.sub.3[60] o-isoC.sub.3 H.sub.7 p-CH.sub.3 p-CH.sub.3[61] o-isoC.sub.3 H.sub.7 o-CH.sub.3 m-CH.sub.3[62] o-isoC.sub.3 H.sub.7 o-CH.sub.3 p-CH.sub.3[63] o-isoC.sub.3 H.sub.7 m-CH.sub.3 p-CH.sub.3[64] m-isoC.sub.3 H.sub.7 o-CH.sub.3 H[65] m-isoC.sub.3 H.sub.7 m-CH.sub.3 H[66] m-isoC.sub.3 H.sub.7 p-CH.sub.3 H[67] m-isoC.sub.3 H.sub.7 o-CH.sub.3 o-CH.sub.3[68] m-isoC.sub.3 H.sub.7 m-CH.sub.3 m-CH.sub.3[69] m-isoC.sub.3 H.sub.7 p-CH.sub.3 p-CH.sub.3[70] m-isoC.sub.3 H.sub.7 o-CH.sub.3 m-CH.sub.3[71] m-isoC.sub.3 H.sub.7 o-CH.sub.3 p-CH.sub.3[72] m-isoC.sub.3 H.sub.7 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR45##CompoundNo. R.sup.1 R R'______________________________________[73] p-isoC.sub.3 H.sub.7 o-CH.sub.3 H[74] p-isoC.sub.3 H.sub.7 m-CH.sub.3 H[75] p-isoC.sub.3 H.sub.7 p-CH.sub.3 H[76] p-isoC.sub.3 H.sub.7 o-CH.sub.3 o-CH.sub.3[77] p-isoC.sub.3 H.sub.7 m-CH.sub.3 m-CH.sub.3[78] p-isoC.sub.3 H.sub.7 p-CH.sub.3 p-CH.sub.3[79] p-isoC.sub.3 H.sub.7 o-CH.sub.3 m-CH.sub.3[80] p-isoC.sub.3 H.sub.7 o-CH.sub.3 p-CH.sub.3[81] p-isoC.sub.3 H.sub.7 m-CH.sub.3 p-CH.sub.3[82] o-n-C.sub.4 H.sub.9 o-CH.sub.3 H[83] o-n-C.sub.4 H.sub.9 m-CH.sub.3 H[84] o-n-C.sub.4 H.sub.9 p-CH.sub.3 H[85] o-n-C.sub.4 H.sub.9 o-CH.sub.3 o-CH.sub.3[86] o-n-C.sub.4 H.sub.9 m-CH.sub.3 m-CH.sub.3[87] o-n-C.sub.4 H.sub.9 p-CH.sub.3 p-CH.sub.3[88] o-n-C.sub.4 H.sub.9 o-CH.sub.3 m-CH.sub.3[89] o-n-C.sub.4 H.sub.9 o-CH.sub.3 p-CH.sub.3[90] o-n-C.sub.4 H.sub.9 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR46##CompoundNo. R.sup.1 R R'______________________________________ [91] m-n-C.sub.4 H.sub.9 o-CH.sub.3 H [92] m-n-C.sub.4 H.sub.9 m-CH.sub.3 H [93] m-n-C.sub.4 H.sub.9 p-CH.sub.3 H [94] m-n-C.sub.4 H.sub.9 o-CH.sub.3 o-CH.sub.3 [95] m-n-C.sub.4 H.sub.9 m-CH.sub.3 m-CH.sub.3 [96] m-n-C.sub.4 H.sub.9 p-CH.sub.3 p-CH.sub.3 [97] m-n-C.sub.4 H.sub.9 o-CH.sub.3 m-CH.sub.3 [98] m-n-C.sub.4 H.sub.9 o-CH.sub.3 p-CH.sub.3 [99] m-n-C.sub.4 H.sub.9 m-CH.sub.3 p-CH.sub.3[100] p-n-C.sub.4 H.sub.9 o-CH.sub.3 H[101] p-n-C.sub.4 H.sub.9 m-CH.sub. 3 H[102] p-n-C.sub.4 H.sub.9 p-CH.sub.3 H[103] p-n-C.sub.4 H.sub.9 o-CH.sub.3 o-CH.sub.3[104] p-n-C.sub.4 H.sub.9 m-CH.sub.3 m-CH.sub.3[105] p-n-C.sub.4 H.sub.9 p-CH.sub.3 p-CH.sub.3[106] p-n-C.sub.4 H.sub.9 o-CH.sub.3 m-CH.sub.3[107] p-n-C.sub.4 H.sub.9 o-CH.sub.3 p-CH.sub.3[108] p-n-C.sub.4 H.sub.9 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR47##CompoundNo. R.sup.1 R R'______________________________________[109] o-terC.sub.4 H.sub.9 o-CH.sub.3 H[110] o-terC.sub.4 H.sub.9 m-CH.sub.3 H[111] o-terC.sub.4 H.sub.9 p-CH.sub.3 H[112] o-terC.sub.4 H.sub.9 o-CH.sub.3 o-CH.sub.3[113] o-terC.sub.4 H.sub.9 m-CH.sub.3 m-CH.sub.3[114] o-terC.sub.4 H.sub.9 p-CH.sub.3 p-CH.sub.3[115] o-terC.sub.4 H.sub.9 o-CH.sub.3 m-CH.sub.3[116] o-terC.sub.4 H.sub.9 o-CH.sub.3 p-CH.sub.3[117] o-terC.sub.4 H.sub.9 m-CH.sub.3 p-CH.sub.3[118] m-terC.sub.4 H.sub.9 o-CH.sub.3 H[119] m-terC.sub.4 H.sub.9 m-CH.sub.3 H[120] m-terC.sub.4 H.sub.9 p-CH.sub.3 H[121] m-terC.sub.4 H.sub.9 o-CH.sub.3 o-CH.sub.3[122] m-terC.sub.4 H.sub.9 m-CH.sub.3 m-CH.sub.3[123] m-terC.sub.4 H.sub.9 p-CH.sub.3 p-CH.sub.3[124] m-terC.sub.4 H.sub.9 o-CH.sub.3 m-CH.sub.3[125] m-terC.sub.4 H.sub.9 o-CH.sub.3 p-CH.sub.3[126] m-terC.sub.4 H.sub.9 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR48##CompoundNo. R.sup.1 R R'______________________________________[127] p-terC.sub.4 H.sub.9 o-CH.sub.3 H[128] p-terC.sub.4 H.sub.9 m-CH.sub.3 H[129] p-terC.sub.4 H.sub.9 p-CH.sub.3 H[130] p-terC.sub.4 H.sub.9 o-CH.sub.3 o-CH.sub.3[131] p-terC.sub.4 H.sub.9 m-CH.sub.3 m-CH.sub.3[132] p-terC.sub.4 H.sub.9 p-CH.sub.3 p-CH.sub.3[133] p-terC.sub.4 H.sub.9 o-CH.sub.3 m-CH.sub.3[134] p-terC.sub.4 H.sub.9 o-CH.sub.3 p-CH.sub.3[135] p-terC.sub.4 H.sub.9 m-CH.sub.3 p-CH.sub.3______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR49##CompoundNo. R.sup.1 Ar.sup.1 Ar.sup.2______________________________________[136] p-C.sub.2 H.sub.5 ##STR50## ##STR51##[137] p-C.sub.2 H.sub.5 ##STR52## ##STR53##[138] p-C.sub.2 H.sub.5 ##STR54## ##STR55##[139] p-C.sub.2 H.sub.5 ##STR56## ##STR57##[140] p-C.sub.2 H.sub.5 ##STR58## ##STR59##[141] p-C.sub.2 H.sub.5 ##STR60## ##STR61##[142] p-C.sub.2 H.sub.5 ##STR62## ##STR63##[143] p-C.sub.2 H.sub.5 ##STR64## ##STR65##[144] p-C.sub.2 H.sub.5 ##STR66## ##STR67##[145] p-C.sub.2 H.sub.5 ##STR68## ##STR69##______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR70##CompoundNo. R.sup.1 Ar.sup.1 Ar.sup.2______________________________________[146] p-C.sub.2 H.sub.5 ##STR71## ##STR72##[147] p-C.sub.2 H.sub.5 ##STR73## ##STR74##[148] p-C.sub.3 H.sub.7 ##STR75## ##STR76##[149] p-C.sub.3 H.sub.7 ##STR77## ##STR78##[150] p-C.sub.2 H.sub.5 ##STR79## ##STR80##[151] p-C.sub.2 H.sub.5 ##STR81## ##STR82##[152] p-C.sub.2 H.sub.5 ##STR83## ##STR84##[153] p-C.sub.2 H.sub.5 ##STR85## ##STR86##[154] p-C.sub.2 H.sub.5 ##STR87## ##STR88##[155] p-C.sub.2 H.sub.5 ##STR89## ##STR90##______________________________________
Examples of Compounds having Formula [III]
______________________________________ ##STR91##Com-poundNo. R.sup.1 Ar.sup.1 Ar.sup.2______________________________________[156] p-C.sub.2 H.sub.5 ##STR92## ##STR93##[157] p-C.sub.3 H.sub.7 ##STR94## ##STR95##[158] p-isoC.sub.3 H.sub.7 ##STR96## ##STR97##[159] p-terC.sub.4 H.sub.9 ##STR98## ##STR99##[160] o-C.sub.2 H.sub.5 ##STR100## ##STR101##[161] p-C.sub.3 H.sub.7 ##STR102## ##STR103##[162] o-C.sub.2 H.sub.5 ##STR104## ##STR105##[163] o-isoC.sub.3 H.sub.7 ##STR106## ##STR107##[164] p-C.sub.4 H.sub.9 ##STR108## ##STR109##[165] p-C.sub.2 H.sub.5 ##STR110## ##STR111##______________________________________ ##STR112##
(wherein X.sub.1 and X.sub.2 represent each a halogen atom, an alkyl group, an alkoxy group, a nitro group, a cyano group, a hydroxy group or a substituted or non-substituted amino group; p and q are each an integer of 0, 1, or 2, provided, p and q are each an integer of 2, X.sub.1 and X.sub.2 may be the same with or the different from each other; and A represents a group represented by the following Formula [F.sub.1 -1]; ##STR113##
(wherein Ar represents a fluorohydrocarbon group, or an aromatic carbocyclic group or an aromatic heterocyclic group having a substituent; Z represents a group consisting of the non-metal atoms each necessary to form a substituted or non-substituted aromatic carbon ring or a substituted or non-substituted aromatic heterocyclic ring; and
m and n are each an integer of 0, 1 or 2, provided m and n are each an integer of 0 at the same time.)
__________________________________________________________________________ ##STR114## Sample Nos. A__________________________________________________________________________ F.sub.1 -1 ##STR115## F.sub.1 -2 ##STR116## F.sub.1 -3 ##STR117## F.sub.1 -4 ##STR118## F.sub.1 -5 ##STR119##__________________________________________________________________________ ##STR120## Azo group substitutedNo. position X.sub.1 a X.sub.1 b X.sub.2 a X.sub.2 b R.sub.1 ' R.sub.2 ' R.sub.3 ' R.sub.4 ' R.sub.5 '__________________________________________________________________________F.sub.1 -6 2, 7 positions 4-F H H H H CF.sub.3 H H HF.sub.1 -7 2, 7 positions 4-F H H H CF.sub.3 H H CF.sub.3 HF.sub.1 -8 2, 7 positions 3-F H 5-F H CF.sub.3 H H H HF.sub.1 -9 2, 7 positions 3-F H 6-OH H H CF.sub.3 H H HF.sub.1 -10 2, 7 positions 4-Cl H H H H CF.sub.3 Cl H HF.sub.1 -11 2, 7 positions 3-Cl H 6-Cl H H CF.sub.3 H H HF.sub.1 -12 2, 7 positions 4-Br H H H H CF.sub.3 H H HF.sub.1 -13 2, 7 positions 4-Br H 5-Br H H H CF.sub.3 H HF.sub.1 -14 2, 7 positions 4-Br 3-Br 6-Br H H CF.sub.3 H H HF.sub.1 -15 2, 7 positions 4-I H H H H CF.sub.3 H H HF.sub.1 -16 2, 7 positions 4-I H H H CF.sub.3 H H CF.sub.3 HF.sub.1 -17 2, 6 positions 4-Cl H H H H CF.sub.3 H H HF.sub.1 -18 3, 6 positions 2-Cl H 7-Cl H H CF.sub.3 H H HF.sub.1 -19 3, 6 positions 4-Br H H H H H CF.sub.3 H HF.sub.1 -20 3, 6 positions 4-I H H H Cl H H CF.sub.3 HF.sub.1 -21 2, 5 positions 3-Br H H H H CF.sub.3 H H HF.sub.1 -22 1, 8 positions 3-Cl H H H H CF.sub.3 H H HF.sub.1 -23 2, 7 positions 4-Br H H H H H H CF.sub.3 HF.sub.1 -24 2, 7 positions 4-I H H H H CF.sub.3 H H Cl__________________________________________________________________________ ##STR121## [wherein, A represents the following coupler; ##STR122##
wherein Y represents a substituted or unsubstituted aromatic group;
R.sub.1 represents a hydrogen atom or one of the following 4 substituted or non-substituted groups; namely,
an alkyl group, an amino group, a carbamoyl group, a carboxy group pr the ester groups thereof and a cyano group;
R.sub.2 represents one of the following 3 groups; namely, an alkyl group, an aralkyl group and an aryl group;
Q.sub.1 represents ##STR123## or an oxygen atom;
Q.sub.2 and Q.sub.3 represent each a hydrogen atom, a cyano group, an alkyl group, a substituted or unsubstituted aromatic group, a halogen atom, a vinyl group, an acyl group or an ester group, provided, Q.sub.2 and Q.sub.3 may be linked to other atomic group so that a ring may be formed;
P.sub.1 and P.sub.2 represent each a hydrogen atom, a halogen atom, a methyl group or a methoxy group.] ##STR124##
(wherein X represents a halogen atom, a nitro group, a cyano group, an acyl group or a carboxy group; n is an integer of 0 to 4; and m is an integer of 0 to 6.) ##STR125##
(wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represent independently H, Cl or Br; and n, m, l and k represent independently an integer of 0 to 4.) ##STR126##

Number	Name	Date
3189447	Neugebauer et al.	Jun 1965
3274000	Noe et al.	Sep 1966
3357989	Byrne et al.	Dec 1967
3820989	Rule et al.	Jun 1974
4724192	Makino et al.	Feb 1988
5032479	Mishima et al.	Jul 1991

Bisstyryl compound and the electrophotographic photoreceptors relating thereto

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