Source: http://www.google.com/patents/US4931350?ie=ISO-8859-1
Timestamp: 2015-03-28 22:49:50
Document Index: 439148058

Matched Legal Cases: ['Application No. 47', 'Application No. 47', 'Application No. 59', 'Application No. 60', 'Application No. 53', 'Application No. 53', 'Application No. 53', 'Application No. 54', 'Application No. 54', 'Application No. 54', 'Application No. 54', 'Application No. 54', 'Application No. 54']

Patent US4931350 - Electrophotographic photoconductor having an arylalkylenearylamino ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsAn electrophotographic photoconductor is disclosed, which comprises an electroconductive support and a photoconductive layer formed thereon comprising at least one amino compound of the formula: ##STR1## wherein A represents a substituted or unsubstituted aromatic hydrocarbon group; R1 and R2 each represent...http://www.google.com/patents/US4931350?utm_source=gb-gplus-sharePatent US4931350 - Electrophotographic photoconductor having an arylalkylenearylamino photoconductorAdvanced Patent SearchPublication numberUS4931350 APublication typeGrantApplication numberUS 07/259,555Publication dateJun 5, 1990Filing dateOct 18, 1988Priority dateJan 20, 1987Fee statusPaidPublication number07259555, 259555, US 4931350 A, US 4931350A, US-A-4931350, US4931350 A, US4931350AInventorsTomoyuki Shimada, Masaomi Sasaki, Mitsuru HashimotoOriginal AssigneeRicoh Company, Ltd.Export CitationBiBTeX, EndNote, RefManPatent Citations (2), Referenced by (5), Classifications (14), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetElectrophotographic photoconductor having an arylalkylenearylamino photoconductor
US 4931350 AAbstract
An electrophotographic photoconductor is disclosed, which comprises an electroconductive support and a photoconductive layer formed thereon comprising at least one amino compound of the formula: ##STR1## wherein A represents a substituted or unsubstituted aromatic hydrocarbon group; R1 and R2 each represent hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; Ar represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic ring; R3 and R4 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, and n is an integer of 0, 1 or 2.
1. An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon comprising at least one amino compound of the formula: ##STR1079## wherein A represents a substituted or unsubstituted aromatic hydrocarbon group; R1 and R2 each represent hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; Ar represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic ring; R3 and R4 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and n is an integer of 0, 1 or 2.
2. The electrophotographic photoconductor as claimed in claim 1, wherein said photoconductive layer further comprises a binder agent which constitutes a charge transporting medium in combination with said amino compound; and a charge generating material dispersed within said charge transporting medium.
3. The electrophotographic photoconductor as claimed in claim 1, wherein said photoconductive layer comprises a charge generating layer containing a charge generating material, and a charge transporting layer containing said amino compound as a charge transporting material.
4. The electrophotographic photoconductor as claimed in claim 1, wherein the thickness of said photoconductive layer is in the range of 3 μm to 50 μm.
5. The electrophotographic photoconductor as claimed in claim 1, wherein the amount of said amino compound is in the range of 30 wt.% to 70 wt.% of the entire weight of said photoconductive layer.
6. The electrophotographic photoconductor as claimed in claim 2, wherein the thickness of said photoconductive layer is in the range of 3 μm to 50 μm.
7. The electrophotographic photoconductor as claimed in claim 2, wherein the amount of said amino compound is in the range of 10 wt.% to 95 wt.% of the entire weight of said photoconductive layer, and the amount of said charge generating material is in the range of 0.1 wt.% to 50 wt.% of the entire weight of said photoconductive layer.
8. The electrophotographic photoconductor as claimed in claim 3, wherein the thickness of said charge generating layer is not more than 5 μm and the thickness of said charge transporting layer is in the range of 3 μm to 50 μm.
9. The electrophotographic photoconductor as claimed in claim 3, wherein the amount of said charge generating material is in the range of 10 wt.% to 95 wt.% of the entire weight of said charge generating layer, and the amount of said amino compound is in the range of 10 wt.% to 95 wt.% of the entire weight of said photoconductive layer.
10. An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed on said electroconductive support comprising at least one amino compound of the formula: ##STR1080## wherein R5 represents hydrogen, an alkyl group, an alkoxy group, an aryloxy group, or halogen; R2 represents hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group; Ar represents a substituted or unsubstituted aromatic hydrocarbon group; and R3 and R4 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.
11. An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed on said electroconductive support comprising at least one amino compound of the formula: ##STR1081## wherein R2 represents hydrogen, or a substituted or unsubstituted phenyl group; R6 represents hydrogen, an alkyl group, an alkoxy group, or halogen; and R3 and R4 each represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.
12. An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed on said electroconductive support comprising at least one amino compound of the formula: ##STR1082## wherein A represents a substituted or unsubstituted aromatic hydrocarbon; R1 represents hydrogen, an alkyl group, or a substituted or unsubstituted phenyl group; and R3 and R4 each represent an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.
13. An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed on said electroconductive support comprising at least one amino compound of the formula: ##STR1083## wherein R1 represents an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; Ar represents a substituted or unsubstituted aromatic hydrocarbon group; R3 and R4 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; and n is an integer of 0 or 1.
14. An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed on said electroconductive support comprising at least one amino compound of the formula: ##STR1084## wherein R7 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryloxy group, a dialkylamino group having 2 to 8 carbon atoms, a diarylamino group, or halogen; Ar represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic ring; and R3 and R4 each represent an alkyl group having 1 to 4 carbon atoms, an aralkyl group, or a substituted or unsubstituted aryl group; and n is an integer of 1 or 2.
15. The electrophotographic photoconductor as claimed in claim 1, in which A, Ar, R3 and R4 are ##STR1085## and R1 R2 are hydrogen.
This is a continuation-in-part of Ser. No. 144 811, filed Jan. 15, 1988, now abandoned.
The present invention relates to an electrophotographic photoconductor, and more particularly to an electrophotographic photoconductor comprising a photoconductive layer containing a particular amino compound overlayed on an electroconductive support.
For instance, a selenium photoconductor, which is widely used at present and sufficiently meets the abovementioned requirements (1) to (3), has the shortcoming that its production is difficult and, accordingly, its production cost is high. Further, it is difficult to work it into the form of a belt due to its poor flexibility, and it is so vulnerable to heat and mechanical shocks that it must be handled with the utmost care.
Recently, organic electrophotographic photoconductors, which are said not to have such shortcomings of the inorganic electrophotographic photoconductors, have been proposed, and some of them are in fact employed for practical use. Representative examples of such organic electrophotographic photoconductors are an electrophotographic photoconductor comprising poly-N-vinylcarbazole and 2,4,7-trinitro-fluorene-9-one (U.S. Pat. No. 3,484,237), a photoconductor in which poly-N-vinylcarbazole is sensitized by a pyrylium salt type dyestuff (Japanese Patent Publication No. 48-25658), a photoconductor containing as the main component an organic pigment (Japanese Laid-Open Patent Application No. 47-37543), and a photoconductor containing as the main component an eutectic crystaline complex (Japanese Laid-Open Patent Application No. 47-10735).
It is therefore an object of the present invention to provide an electrophotographic photoconductor or element comprising a photoconductive layer containing a particular amino compound and an electroconductive support for supporting the photoconductive layer thereon, with high photosensitivity, which does not give rise to difficulties in producing the electrophotographic photoconductor, and which is comparatively inexpensive and excellent in durability.
The particular amino compound employed in the present invention is represented by the following general formula (I): ##STR2## wherein A represents a substituted or unsubstituted aromatic hydrocarbon group; R1 and R2 each represent hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; Ar represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic ring such as a thiophene group; R3 and R4 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; and n is 0, 1 or 2.
The electrophotographic photoconductor according to the present invention is characterized by having a photoconductive layer which comprises at least one amino compound of the following general formula (I): ##STR3## wherein A represents a substituted or unsubstituted aromatic hydrocarbon group; R1 and R2 each represent hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; Ar represents a substituted or unsubstituted aromatic hydrocarbon group, or a heterocyclic ring such as a thiophene group; R3 and R4 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; and n is an integer of 0, 1 or 2.
In the above general formula (I), it is preferable that the aromatic hydrocarbon group represented by A be a phenyl group which may have a substituent or an anthracene group which may have a substituent and that the aromatic hydrocarbon group represented by Ar also be a phenyl group which may have a substituent. In the formula (I), examples of the substituent of the aromatic hydrocarbon group such as the phenyl group and the anthracene group are an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenoxy group, and halogen.
Examples of the amino compound represented by the above general formula (I) are as follows:
__________________________________________________________________________ ##STR4##AminoCompound n A      R1               R2                   Ar      R3, R4__________________________________________________________________________(I)-1 0    ##STR5##          H    H, alkyl, sub. or unsub. phenyl                   sub. or unsub. aromatic hydro- carbon                           sub. or unsub. alkyl, sub. or unsub.                           aralkyl, sub. or unsub. aryl(I)-2 0    ##STR6##          H    H, sub. or unsub. phenyl                    ##STR7##                           sub. or unsub. alkyl, sub. or unsub.                           aralkyl, sub. or unsub. aryl(I)-3 0 sub. or  unsub. aromatic hydro- carbon          H, sub. or unsub. alkyl, sub. or unsub. phenyl               H                    ##STR8##                           sub. or unsub. alkyl, sub, or unsub.                           aralkyl, sub. or unsub. aryl(I)-4 0 sub. or          sub. or               H   sub. or sub. or unsub. or   unsub. unsub.   unsub.  alkyl, sub. or 1 phenyl alkyl,   aromatic                           unsub. aralkyl,          sub. or  hydro-  sub. or unsub.          unsub.   carbon  aryl          aryl, sub.          or unsub.          aralkyl(I)-5 1 or 2    ##STR9##          H    H   sub. or unsub. aromatic hydro- carbon, or sub. or                   nsub. hetero- cyclic ring                           sub. or unsub. alkyl, or sub. or unsub.                           aryl__________________________________________________________________________
In amino compound (I)-1, R5 represents hydrogen, an alkyl group, an alkoxy group, an aryloxy group or halogen.
In amino compound (I)-2, R6 represents hydrogen, an alkyl group, an alkoxy group or halogen.
In amino compound (I)-5, R7 represents hydrogen, an alkyl group, preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group, preferably an alkoxy group having 1 to 4 carbon atoms, an aryloxy group, a dialkylamino group, a diarylamino group or halogen; and R3 and R4 each represents an alkyl group having 1 to 4 carbon atoms, an aralkyl group, or a substituted or unsubstituted aryl group.
Referring to the accompanying drawing, embodiments of an electrophotographic photoconductor according to the present invention will now be explained.
In FIGS. 1 to 3, reference numeral 1 indicates an electroconductive support; reference numerals 2a, 2b and 2c each indicate a photoconductive layer; reference numeral 3, a charge generating material; reference numeral 4, a charge transporting medium; reference numeral 5, a charge generating layer; and reference numeral 6, a charge transporting layer.
The amino compound (I)-1 can be prepared by catalytic hydrogenation of the stilbene compounds described in Japanese Laid-Open Patent Applications Nos. 57-73076, 57-178799, 57-205437, 57-207252, 58-24696 and 58-69202. Specific examples of the amino compound (I)-1 are shown in Table 1.
The amino compound (I)-2 can be prepared by catalytic hydrogenation of the naphthalene compounds described in Japanese Laid-Open Patent Application No. 59-68750. Specific examples of the amino compound (I)-1 are shown in Table 2.
The amino compound (I)-3 can be prepared by catalytic hydrogenation of the thiophene compounds described in Japanese Laid-Open Patent Application No. 60-93443. Specific examples of the amino compound (I)-3 are shown in Table 3.
The amino compounds (I)-4 can be prepared by catalytic hydrogenation of the stilbene compounds described in Japanese Laid-Open Patent Applications Nos. 58-198425, 59-191057, 58-64529, 58-87624 and 58-201025. Specific examples of the amino compounds (I)-4 are respectively shown in Table 4.
The amino compound (I)-5 can be prepared by catalytic hydrogenation of the unsaturated amino compound of the following formula: ##STR10## wherein R3, R4, R7 and n are respectively the same as defined previously. Specific examples of the amino compound (I)-5 are shown in Table 5.
TABLE 1__________________________________________________________________________Amino Compound (I)-1 ##STR11##AminoCompounds R5 R2     Ar      R3    R4__________________________________________________________________________(I)-1-1 H          ##STR12##                      ##STR13##                             CH3   CH3(I)-1-2 H       H                      ##STR14##                             C2 H5                                        C2 H5(I)-1-3 H       H                      ##STR15##                             CH3   CH3(I)-1-4 H       H                      ##STR16##                              ##STR17##                                         ##STR18##(I)-1-5 H       H                      ##STR19##                             CH3                                         ##STR20##(I)-1-6 H       H                      ##STR21##                              ##STR22##                                         ##STR23##(I)-1-7 H       H                      ##STR24##                              ##STR25##                                         ##STR26##(I)-1-8 H       H                      ##STR27##                              ##STR28##                                         ##STR29##(I)-1-9 H       H                      ##STR30##                              ##STR31##                                         ##STR32##(I)-1-10 H       H                      ##STR33##                              ##STR34##                                         ##STR35##(I)-1-11 H       H                      ##STR36##                              ##STR37##                                         ##STR38##(I)-1-12 H       H                      ##STR39##                              ##STR40##                                         ##STR41##(I)-1-13 H       H                      ##STR42##                              ##STR43##                                         ##STR44##(I)-1-14 H       H                      ##STR45##                              ##STR46##                                         ##STR47##(I)-1-15 H       H                      ##STR48##                              ##STR49##                                         ##STR50##(I)-1-16 H       H                      ##STR51##                              ##STR52##                                         ##STR53##(I)-1-17 H       H                      ##STR54##                              ##STR55##                                         ##STR56##(I)-1-18 4-CH3         H                      ##STR57##                              ##STR58##                                         ##STR59##(I)-1-19 4-CH3         H                      ##STR60##                              ##STR61##                                         ##STR62##(I)-1-20 4-CH3         H                      ##STR63##                              ##STR64##                                         ##STR65##(I)-1-21 4-CH3         H                      ##STR66##                              ##STR67##                                         ##STR68##(I)-1-22 4-CH3         H                      ##STR69##                              ##STR70##                                         ##STR71##(I)-1-23 4-CH3         H                      ##STR72##                              ##STR73##                                         ##STR74##(I)-1-24 4-CH3         H                      ##STR75##                              ##STR76##                                         ##STR77##(I)-1-25 4-CH3         H                      ##STR78##                             C2 H5                                        C2 H5(I)-1-26 4-CH3         H                      ##STR79##                              ##STR80##                                         ##STR81##(I)-1-27 4-CH3         H                      ##STR82##                              ##STR83##                                         ##STR84##(I)-1-28 4-CH3         H                      ##STR85##                              ##STR86##                                         ##STR87##(I)-1-29 4-C2 H5         H                      ##STR88##                              ##STR89##                                         ##STR90##(I)-1-30 4-C2 H5         H                      ##STR91##                              ##STR92##                                         ##STR93##(I)-1-31 4-C2 H5         H                      ##STR94##                              ##STR95##                                         ##STR96##(I)-1-32 4-C2 H5         H                      ##STR97##                              ##STR98##                                         ##STR99##(I)-1-33 4-C2 H5         H                      ##STR100##                              ##STR101##                                         ##STR102##(I)-1-34 4-C2 H5         H                      ##STR103##                              ##STR104##                                         ##STR105##(I)-1-35 4-C2 H5         H                      ##STR106##                              ##STR107##                                         ##STR108##(I)-1-36 4-C2 H5         H                      ##STR109##                              ##STR110##                                         ##STR111##(I)-1-37 4-C2 H5         H                      ##STR112##                             CH3   CH3(I)-1-38 4-C2 H5         H                      ##STR113##                              ##STR114##                                         ##STR115##(I)-1-39 4-C2 H5         H                      ##STR116##                              ##STR117##                                         ##STR118##(I)-1-40 4-Cl    H                      ##STR119##                              ##STR120##                                         ##STR121##(I)-1-41 4-Cl    H                      ##STR122##                              ##STR123##                                         ##STR124##(I)-1-42 4-Cl    H                      ##STR125##                              ##STR126##                                         ##STR127##(I)-1-43 4-Cl    H                      ##STR128##                              ##STR129##                                         ##STR130##(I)-1-44 4-Cl    H                      ##STR131##                              ##STR132##                                         ##STR133##(I)-1-45 4-Cl    H                      ##STR134##                              ##STR135##                                         ##STR136##(I)-1-46 4-Cl    H                      ##STR137##                             CH3   CH3(I)-1-47 2-Cl    H                      ##STR138##                              ##STR139##                                         ##STR140##(I)-1-48 2-Cl    H                      ##STR141##                              ##STR142##                                         ##STR143##(I)-1-49 2-Cl    H                      ##STR144##                              ##STR145##                                         ##STR146##(I)-1-50 2-Cl    H                      ##STR147##                              ##STR148##                                         ##STR149##(I)-1-51 2-Cl    H                      ##STR150##                              ##STR151##                                         ##STR152##(I)-1-52 2-Cl    H                      ##STR153##                              ##STR154##                                         ##STR155##(I)-1-53 4-OCH3         H                      ##STR156##                              ##STR157##                                         ##STR158##(I)-1-54 4-OCH3         H                      ##STR159##                              ##STR160##                                         ##STR161##(I)-1-55 4-OCH3         H                      ##STR162##                              ##STR163##                                         ##STR164##(I)-1-56 4-OCH3         H                      ##STR165##                              ##STR166##                                         ##STR167##(I)-1-57 4-OCH3         H                      ##STR168##                              ##STR169##                                         ##STR170##(I)-1-58 4-OCH3         H                      ##STR171##                              ##STR172##                                         ##STR173##(I)-1-59 4-OCH3         H                      ##STR174##                              ##STR175##                                         ##STR176##(I)-1-60 4-OCH3         H                      ##STR177##                              ##STR178##                                         ##STR179##(I)-1-61 4-OCH3         H                      ##STR180##                             CH3   CH3(I)-1-62 4-OCH3         H                      ##STR181##                             C2 H5                                         ##STR182##(I)-1-63 4-OCH3         H                      ##STR183##                              ##STR184##                                         ##STR185##(I)-1-64 4-OCH3         H                      ##STR186##                              ##STR187##                                         ##STR188##(I)-1-65 4-OCH3         H                      ##STR189##                              ##STR190##                                         ##STR191##(I)-1-66  ##STR192##         H                      ##STR193##                              ##STR194##                                         ##STR195##(I)-1-67  ##STR196##         H                      ##STR197##                              ##STR198##                                         ##STR199##(I)-1-68  ##STR200##         H                      ##STR201##                              ##STR202##                                         ##STR203##(I)-1-69  ##STR204##         H                      ##STR205##                              ##STR206##                                         ##STR207##(I)-1-70  ##STR208##         H                      ##STR209##                              ##STR210##                                         ##STR211##(I)-1-71  ##STR212##         H                      ##STR213##                              ##STR214##                                         ##STR215##(I)-1-72  ##STR216##         H                      ##STR217##                             CH3                                         ##STR218##(I)-1-73  ##STR219##         H                      ##STR220##                              ##STR221##                                         ##STR222##(I)-1-74  ##STR223##         H                      ##STR224##                             C2 H5                                        C2 H5(I)-1-75  ##STR225##         H                      ##STR226##                              ##STR227##                                         ##STR228##(I)-1-76  ##STR229##         H                      ##STR230##                              ##STR231##                                         ##STR232##(I)-1-77  ##STR233##         H                      ##STR234##                              ##STR235##                                         ##STR236##(I)-1-78 H          ##STR237##                      ##STR238##                              ##STR239##                                         ##STR240##(I)-1-79 H          ##STR241##                      ##STR242##                              ##STR243##                                         ##STR244##__________________________________________________________________________
TABLE 2__________________________________________________________________________Amino Compound (I)-2 ##STR245##AminoCompounds R2     R6                  R3         R4__________________________________________________________________________(I)-2-1 H           H    CH3        CH3(I)-2-2 H           H    C2 H5 C2 H5(I)-2-3 H           H    CH3                                   ##STR246##(I)-2-4 H           H    CH3                                   ##STR247##(I)-2-5 H           H    C2 H5                                   ##STR248##(I)-2-6 H           H                   ##STR249##                                   ##STR250##(I)-2-7 H           H                   ##STR251##                                   ##STR252##(I)-2-8 H           H                   ##STR253##                                   ##STR254##(I)-2-9 H           H                   ##STR255##                                   ##STR256##(I)-2-10 H           H                   ##STR257##                                   ##STR258##(I)-2-11 H           H                   ##STR259##                                   ##STR260##(I)-2-12 H           H                   ##STR261##                                   ##STR262##(I)-2-13 H           H                   ##STR263##                                   ##STR264##(I)-2-14 H           H                   ##STR265##                                   ##STR266##(I)-2-15 H           H                   ##STR267##                                   ##STR268##(I)-2-16 H           H                   ##STR269##                                   ##STR270##(I)-2-17 H           H                   ##STR271##                                   ##STR272##(I)-2-18 H           H                   ##STR273##                                   ##STR274##(I)-2-19 H           H                   ##STR275##                                   ##STR276##(I)-2-20 H           H                   ##STR277##                                   ##STR278##(I)-2-21 H           H                   ##STR279##                                   ##STR280##(I)-2-22 H           H                   ##STR281##                                   ##STR282##(I)-2-23 H           H                   ##STR283##                                   ##STR284##(I)-2-24 H           H                   ##STR285##                                   ##STR286##(I)-2-25 H           H                   ##STR287##                                   ##STR288##(I)-2-26 H           H                   ##STR289##     CH3(I)-2-27 H           H                   ##STR290##     C2 H5(I)-2-28 H           H                   ##STR291##                                   ##STR292##(I)-2-29 H           H                   ##STR293##                                   ##STR294##(I)-2-30 H           H                   ##STR295##                                   ##STR296##(I)-2-31 H           H                   ##STR297##                                   ##STR298##(I)-2-32 H           H                   ##STR299##                                   ##STR300##(I)-2-33 H           H                   ##STR301##                                   ##STR302##(I)-2-34 H           H                   ##STR303##                                   ##STR304##(I)-2-35 H           H                   ##STR305##                                   ##STR306##(I)-2-36 H           H                   ##STR307##                                   ##STR308##(I)-2-37 H           H                   ##STR309##                                   ##STR310##(I)-2-38 H           H                   ##STR311##                                   ##STR312##(I)-2-39 H           H                   ##STR313##                                   ##STR314##(I)-2-40 H           H                   ##STR315##                                   ##STR316##(I)-2-41 H           H                   ##STR317##                                   ##STR318##(I)-2-42 H           H                   ##STR319##                                   ##STR320##(I)-2-43 H           H                   ##STR321##                                   ##STR322##(I)-2-44 H           H                   ##STR323##                                   ##STR324##(I)-2-45 H           H                   ##STR325##                                   ##STR326##(I)-2-46 H           H                   ##STR327##                                   ##STR328##(I)-2-47 H           H                   ##STR329##                                   ##STR330##(I)-2-48 H           H                   ##STR331##                                   ##STR332##(I)-2-49 H           2-CH3                  CH3        CH3(I)-2-50 H           2-CH3                  CH3                                   ##STR333##(I)-2-51 H           2-CH3                   ##STR334##                                   ##STR335##(I)-2-52 H           2-CH3                   ##STR336##                                   ##STR337##(I)-2-53 H           2-CH3                   ##STR338##                                   ##STR339##(I)-2-54 H           2-CH3                   ##STR340##                                   ##STR341##(I)-2-55 H           2-CH3                   ##STR342##                                   ##STR343##(I)-2-56 H           2-CH3                   ##STR344##                                   ##STR345##(I)-2-57 H           2-CH3                   ##STR346##                                   ##STR347##(I)-2-58 H           2-CH3                   ##STR348##                                   ##STR349##(I)-2-59 H           2-CH3                   ##STR350##                                   ##STR351##(I)-2-60 H           2-CH3                  C2 H5 C2 H5(I)-2-61 H           2-CH3                  C2 H5                                   ##STR352##(I)-2-62 H           2-CH3                   ##STR353##                                   ##STR354##(I)-2-63 H           2-CH3                   ##STR355##                                   ##STR356##(I)-2-64 H           2-CH3                   ##STR357##                                   ##STR358##(I)-2-65 H           2-CH3                   ##STR359##                                   ##STR360##(I)-2-66 H           2-CH3                   ##STR361##                                   ##STR362##(I)-2-67 H           2-CH3                   ##STR363##                                   ##STR364##(I)-2-68 H           3-CH3                  CH3        CH3(I)-2-69 H           3-CH3                  CH3                                   ##STR365##(I)-2-70 H           3-CH3                  C2 H5 C2 H5(I)-2-71 H           3-CH3                  C2 H5                                   ##STR366##(I)-2-72 H           3-CH3                   ##STR367##                                   ##STR368##(I)-2-73 H           3-CH3                   ##STR369##                                   ##STR370##(I)-2-74 H           3-CH3                   ##STR371##                                   ##STR372##(I)-2-75 H           3-CH3                   ##STR373##                                   ##STR374##(I)-2-76 H           3-CH3                   ##STR375##                                   ##STR376##(I)-2-77 H           3-CH3                   ##STR377##                                   ##STR378##(I)-2-78 H           3-CH3                   ##STR379##                                   ##STR380##(I)-2-79 H           3-CH3                   ##STR381##                                   ##STR382##(I)-2-80 H           3-CH3                   ##STR383##                                   ##STR384##(I)-2-81 H           3-CH3                  C2 H5 C2 H5(I)-2-82 H           3-CH3                  C2 H5                                   ##STR385##(I)-2-83 H           3-CH3                   ##STR386##                                   ##STR387##(I)-2-84 H           3-CH3                   ##STR388##                                   ##STR389##(I)-2-85 H           3-CH3                   ##STR390##                                   ##STR391##(I)-2-86 H           3-CH3                   ##STR392##                                   ##STR393##(I)-2-87 H           3-CH3                   ##STR394##                                   ##STR395##(I)-2-88 H           3-CH3                   ##STR396##                                   ##STR397##(I)-2-89 H           2-Cl                   ##STR398##                                   ##STR399##(I)-2-90 H           2-Cl                   ##STR400##                                   ##STR401##(I)-2-91 H           2-Cl                   ##STR402##                                   ##STR403##(I)-2-92 H           2-OCH3                   ##STR404##                                   ##STR405##(I)-2-93 H           2-OCH3                   ##STR406##                                   ##STR407##(I)-2-94 H           2-OCH3                   ##STR408##                                   ##STR409##(I)-2-95 H           2-OCH3                   ##STR410##                                   ##STR411##(I)-2-96  ##STR412## H    CH3        CH3(I)-2-97  ##STR413## H                   ##STR414##                                   ##STR415##(I)-2-98  ##STR416## H                   ##STR417##                                   ##STR418##(I)-2-99  ##STR419## H                   ##STR420##                                   ##STR421##(I)-2-100  ##STR422## H                   ##STR423##                                   ##STR424##(I)-2-101  ##STR425## H                   ##STR426##                                   ##STR427##(I)-2-102  ##STR428## H    CH3        CH3(I)-2-103 H           H                   ##STR429##                                   ##STR430##__________________________________________________________________________
TABLE 3__________________________________________________________________________Amino Compound (I)-3 ##STR431##AminoCompounds A            R1   R3    R4__________________________________________________________________________(I)-3-1  ##STR432##  H                         ##STR433##                                   CH3(I)-3-2  ##STR434##  H                         ##STR435##                                    ##STR436##(I)-3-3  ##STR437##  H                         ##STR438##                                    ##STR439##(I)-3-4  ##STR440##  H                         ##STR441##                                    ##STR442##(I)-3-5  ##STR443##  H                         ##STR444##                                    ##STR445##(I)-3-6  ##STR446##  H                         ##STR447##                                    ##STR448##(I)-3-7  ##STR449##  H                         ##STR450##                                    ##STR451##(I)-3-8  ##STR452##  H                         ##STR453##                                    ##STR454##(I)-3-9  ##STR455##  H                         ##STR456##                                    ##STR457##(I)-3-10  ##STR458##  H                         ##STR459##                                    ##STR460##(I)-3-11  ##STR461##  H                         ##STR462##                                   C2 H5(I)-3-12  ##STR463##  H                         ##STR464##                                    ##STR465##(I)-3-13  ##STR466##  H                         ##STR467##                                    ##STR468##(I)-3-14  ##STR469##  H                         ##STR470##                                    ##STR471##(I)-3-15  ##STR472##  H                         ##STR473##                                    ##STR474##(I)-3-16  ##STR475##  H                         ##STR476##                                    ##STR477##(I)-3-17  ##STR478##  H                         ##STR479##                                    ##STR480##(I)-3-18  ##STR481##  H                         ##STR482##                                    ##STR483##(I)-3-19  ##STR484##  H                         ##STR485##                                    ##STR486##(I)-3-20  ##STR487##  H                         ##STR488##                                    ##STR489##(I)-3-21  ##STR490##  CH3                         ##STR491##                                   C2 H5(I)-3-22  ##STR492##  CH3                         ##STR493##                                    ##STR494##(I)-3-23  ##STR495##  CH3                         ##STR496##                                    ##STR497##(I)-3-24  ##STR498##  CH3                         ##STR499##                                    ##STR500##(I)-3-25  ##STR501##  CH3                         ##STR502##                                    ##STR503##(I)-3-26  ##STR504##  CH3                         ##STR505##                                    ##STR506##(I)-3-27  ##STR507##  CH3                         ##STR508##                                    ##STR509##(I)-3-28  ##STR510##  CH3                         ##STR511##                                    ##STR512##(I)-3-29  ##STR513##               ##STR514##                         ##STR515##                                    ##STR516##(I)-3-30  ##STR517##               ##STR518##                         ##STR519##                                    ##STR520##(I)-3-31  ##STR521##               ##STR522##                         ##STR523##                                    ##STR524##(I)-3-32  ##STR525##               ##STR526##                         ##STR527##                                    ##STR528##(I)-3-33  ##STR529##               ##STR530##                         ##STR531##                                    ##STR532##(I)-3-34  ##STR533##               ##STR534##                         ##STR535##                                    ##STR536##(I)-3-35  ##STR537##               ##STR538##                         ##STR539##                                    ##STR540##(I)-3-36  ##STR541##  H                         ##STR542##                                    ##STR543##(I)-3-37  ##STR544##  H                         ##STR545##                                    ##STR546##(I)-3-38  ##STR547##  H                         ##STR548##                                    ##STR549##(I)-3-39  ##STR550##  H                         ##STR551##                                    ##STR552##(I)-3-40  ##STR553##  H                         ##STR554##                                    ##STR555##(I)-3-41  ##STR556##  H                         ##STR557##                                    ##STR558##(I)-3-42  ##STR559##  H                         ##STR560##                                    ##STR561##(I)-3-43  ##STR562##  H                         ##STR563##                                    ##STR564##(I)-3-44  ##STR565##  H                         ##STR566##                                    ##STR567##(I)-3-45  ##STR568##  H                         ##STR569##                                    ##STR570##(I)-3-46  ##STR571##  H                         ##STR572##                                    ##STR573##(I)-3-47  ##STR574##               ##STR575##                         ##STR576##                                    ##STR577##__________________________________________________________________________
TABLE 4__________________________________________________________________________Amino Compound (I)-4 ##STR578##AminoCompounds R1   n Ar      R3    R4__________________________________________________________________________(I)-4-1 CH3  0              ##STR579##                     CH3   CH3(I)-4-2 CH3  0              ##STR580##                     C2 H5                                C2 H5(I)-4-3 CH3  0              ##STR581##                      ##STR582##                                 ##STR583##(I)-4-4 CH3  0              ##STR584##                      ##STR585##                                 ##STR586##(I)-4-5  CH3 0              ##STR587##                      ##STR588##                                 ##STR589##(I)-4-6 CH3  0              ##STR590##                      ##STR591##                                 ##STR592##(I)-4-7 CH3  0              ##STR593##                      ##STR594##                                 ##STR595##(I)-4-8 CH3  0              ##STR596##                      ##STR597##                                 ##STR598##(I)-4-9 CH3  0              ##STR599##                      ##STR600##                                 ##STR601##(I)-4-10 CH3  0              ##STR602##                      ##STR603##                                 ##STR604##(I)-4-11 CH3  0              ##STR605##                      ##STR606##                                 ##STR607##(I)-4-12 CH3  0              ##STR608##                      ##STR609##                                 ##STR610##(I)-4-13 CH3  0              ##STR611##                      ##STR612##                                 ##STR613##(I)-4-14 CH3  0              ##STR614##                      ##STR615##                                 ##STR616##(I)-4-15  ##STR617##           0              ##STR618##                     CH3   CH3(I)-4-16  ##STR619##           0              ##STR620##                     C2 H5                                C2 H5(I)-4-17  ##STR621##           0              ##STR622##                      ##STR623##                                 ##STR624##(I)-4-18  ##STR625##           0              ##STR626##                      ##STR627##                                 ##STR628##(I)-4-19  ##STR629##           0              ##STR630##                      ##STR631##                                 ##STR632##(I)-4-20  ##STR633##           0              ##STR634##                      ##STR635##                                 ##STR636##(I)-4-21  ##STR637##           0              ##STR638##                      ##STR639##                                 ##STR640##(I)-4-22  ##STR641##           0              ##STR642##                      ##STR643##                                 ##STR644##(I)-4-23  ##STR645##           0              ##STR646##                      ##STR647##                                 ##STR648##(I)-4-24  ##STR649##           0              ##STR650##                      ##STR651##                                 ##STR652##(I)-4-25  ##STR653##           0              ##STR654##                      ##STR655##                                 ##STR656##(I)-4-26  ##STR657##           0              ##STR658##                      ##STR659##                                 ##STR660##(I)-4-27  ##STR661##           0              ##STR662##                      ##STR663##                                 ##STR664##(I)-4-28  ##STR665##           0              ##STR666##                      ##STR667##                                 ##STR668##(I)-4-29  ##STR669##           0              ##STR670##                      ##STR671##                                 ##STR672##(I)-4-30  ##STR673##           0              ##STR674##                      ##STR675##                                 ##STR676##(I)-4-31  ##STR677##           0              ##STR678##                      ##STR679##                                 ##STR680##(I)-4-32  ##STR681##           0              ##STR682##                     CH3   CH3(I)-4-33  ##STR683##           0              ##STR684##                     C2 H5                                C2 H5(I)-4-34  ##STR685##           0              ##STR686##                      ##STR687##                                 ##STR688##(I)-4-35  ##STR689##           0              ##STR690##                      ##STR691##                                 ##STR692##(I)-4-36  ##STR693##           0              ##STR694##                     CH3                                 ##STR695##(I)-4-37  ##STR696##           0              ##STR697##                      ##STR698##                                 ##STR699##(I)-4-38  ##STR700##           0              ##STR701##                      ##STR702##                                 ##STR703##(I)-4-39  ##STR704##           0              ##STR705##                      ##STR706##                                 ##STR707##(I)-4-40  ##STR708##           0              ##STR709##                      ##STR710##                                 ##STR711##(I)-4-41  ##STR712##           0              ##STR713##                      ##STR714##                                 ##STR715##(I)-4-42 CH3  1              ##STR716##                      ##STR717##                                 ##STR718##(I)-4-43 CH3  1              ##STR719##                      ##STR720##                                 ##STR721##(I)-4-44  ##STR722##           1              ##STR723##                     CH3   CH3(I)-4-45  ##STR724##           1              ##STR725##                      ##STR726##                                 ##STR727##(I)-4-46  ##STR728##           1              ##STR729##                      ##STR730##                                 ##STR731##(I)-4-47  ##STR732##           1              ##STR733##                      ##STR734##                                 ##STR735##(I)-4-48  ##STR736##           1              ##STR737##                      ##STR738##                                 ##STR739##(I)-4-49  ##STR740##           1              ##STR741##                      ##STR742##                                 ##STR743##(I)-4-50  ##STR744##           1              ##STR745##                      ##STR746##                                 ##STR747##(I)-4-51  ##STR748##           1              ##STR749##                      ##STR750##                                 ##STR751##(I)-4-52  ##STR752##           1              ##STR753##                      ##STR754##                                 ##STR755##__________________________________________________________________________
TABLE 5__________________________________________________________________________Amino Compound (I)-5 ##STR756##AminoCompounds R7 n Ar      R3        R4__________________________________________________________________________(I)-5-1 H       1            ##STR757##                   CH3       CH3(I)-5-2 H       1            ##STR758##                    ##STR759##    CH3(I)-5-3 H       1            ##STR760##                   CH3                                   ##STR761##(I)-5-4 H       1            ##STR762##                    ##STR763##                                   ##STR764##(I)-5-5 H       1            ##STR765##                    ##STR766##                                   ##STR767##(I)-5-6 H       1            ##STR768##                    ##STR769##                                   ##STR770##(I)-5-7 H       1            ##STR771##                    ##STR772##                                   ##STR773##(I)-5-8 H       1            ##STR774##                    ##STR775##                                   ##STR776##(I)-5-9 H       1            ##STR777##                    ##STR778##                                   ##STR779##(I)-5-10 H       1            ##STR780##                    ##STR781##                                   ##STR782##(I)-5-11 H       1            ##STR783##                    ##STR784##                                   ##STR785##(I)-5-12 H       1            ##STR786##                    ##STR787##                                   ##STR788##(I)-5-13 H       1            ##STR789##                    ##STR790##                                   ##STR791##(I)-5-14 H       1            ##STR792##                    ##STR793##                                   ##STR794##(I)-5-15 H       1            ##STR795##                    ##STR796##                                   ##STR797##(I)-5-16 H       1            ##STR798##                    ##STR799##                                   ##STR800##(I)-5-17 H       1            ##STR801##                    ##STR802##                                   ##STR803##(I)-5-18 H       1            ##STR804##                    ##STR805##                                   ##STR806##(I)-5-19 H       1            ##STR807##                    ##STR808##                                   ##STR809##(I)-5-20 H       1            ##STR810##                    ##STR811##                                   ##STR812##(I)-5-21 H       1            ##STR813##                   CH3                                   ##STR814##(I)-5-22 H       1            ##STR815##                    ##STR816##                                   ##STR817##(I)-5-23 H       1            ##STR818##                    ##STR819##                                   ##STR820##(I)-5-24 H       1            ##STR821##                    ##STR822##                                   ##STR823##(I)-5-25 H       1            ##STR824##                    ##STR825##                                   ##STR826##(I)-5-26 H       1            ##STR827##                    ##STR828##                                   ##STR829##(I)-5-27 H       1            ##STR830##                    ##STR831##                                   ##STR832##(I)-5-28 H       1            ##STR833##                    ##STR834##                                   ##STR835##(I)-5-29 H       1            ##STR836##                    ##STR837##                                   ##STR838##(I)-5-30 H       1            ##STR839##                    ##STR840##                                   ##STR841##(I)-5-31 H       1            ##STR842##                   CH3       CH3(I)-5-32 H       1            ##STR843##                    ##STR844##                                   ##STR845##(I)-5-33 H       1            ##STR846##                    ##STR847##                                   ##STR848##(I)-5-34 H       1            ##STR849##                    ##STR850##                                   ##STR851##(I)-5-35 H       1            ##STR852##                    ##STR853##                                   ##STR854##(I)-5-36 H       1            ##STR855##                    ##STR856##                                   ##STR857##(I)-5-37 H       2            ##STR858##                    ##STR859##                                   ##STR860##(I)-5-38 H       2            ##STR861##                    ##STR862##                                   ##STR863##(I)-5-39 H       2            ##STR864##                    ##STR865##                                   ##STR866##(I)-5-40 H       2            ##STR867##                    ##STR868##                                   ##STR869##(I)-5-41 H       2            ##STR870##                   CH3       CH3(I)-5-42 H       2            ##STR871##                   CH3                                   ##STR872##(I)-5-43 H       2            ##STR873##                    ##STR874##                                   ##STR875##(I)-5-44 H       2            ##STR876##                    ##STR877##                                   ##STR878##(I)-5-45 H       2            ##STR879##                    ##STR880##                                   ##STR881##(I)-5-46 H       2            ##STR882##                    ##STR883##                                   ##STR884##(I)-5-47 H       2            ##STR885##                    ##STR886##                                   ##STR887##(I)-5-48 H       2            ##STR888##                    ##STR889##                                   ##STR890##(I)-5-49 H       2            ##STR891##                    ##STR892##                                   ##STR893##(I)-5-50 H       2            ##STR894##                    ##STR895##                                   ##STR896##(I)-5-51 H       2            ##STR897##                    ##STR898##                                   ##STR899##(I)-5-52 H       2            ##STR900##                    ##STR901##                                   ##STR902##(I)-5-53 H       2            ##STR903##                    ##STR904##                                   ##STR905##(I)-5-54 H       2            ##STR906##                    ##STR907##                                   ##STR908##(I)-5-55 H       2            ##STR909##                    ##STR910##                                   ##STR911##(I)-5-56 H       2            ##STR912##                    ##STR913##                                   ##STR914##(I)-5-57 H       2            ##STR915##                    ##STR916##                                   ##STR917##(I)-5-58 p-CH3         1            ##STR918##                    ##STR919##                                   ##STR920##(I)-5-59 p-CH3         1            ##STR921##                    ##STR922##                                   ##STR923##(I)-5-60 p-CH3         1            ##STR924##                    ##STR925##                                   ##STR926##(I)-5-61 p-CH3         1            ##STR927##                    ##STR928##                                   ##STR929##(I)-5-62 p-CH3         1            ##STR930##                    ##STR931##                                   ##STR932##(I)-5-63 p-CH3         2            ##STR933##                    ##STR934##                                   ##STR935##(I)-5-64 p-CH3         2            ##STR936##                    ##STR937##                                   ##STR938##(I)-5-65 p-CH3         2            ##STR939##                    ##STR940##                                   ##STR941##(I)-5-66 p-CH3         2            ##STR942##                    ##STR943##                                   ##STR944##(I)-5-67 p-CH3         1            ##STR945##                    ##STR946##                                   ##STR947##(I)-5-68 p-CH3         1            ##STR948##                    ##STR949##                                   ##STR950##(I)-5-69 p-CH3         1            ##STR951##                    ##STR952##                                   ##STR953##(I)-5-70 p-CH3         1            ##STR954##                    ##STR955##                                   ##STR956##(I)-5-71 p-OCH3         1            ##STR957##                    ##STR958##                                   ##STR959##(I)-5-72 p-OCH3         1            ##STR960##                    ##STR961##                                   ##STR962##(I)-5-73 p-OCH3         1            ##STR963##                    ##STR964##                                   ##STR965##(I)-5-74 p-OCH3         2            ##STR966##                    ##STR967##                                   ##STR968##(I)-5-75 p-Cl    1            ##STR969##                    ##STR970##                                   ##STR971##(I)-5-76 p-Cl    1            ##STR972##                    ##STR973##                                   ##STR974##(I)-5-77 p-Cl    1            ##STR975##                    ##STR976##                                   ##STR977##(I)-5-78 p-Cl    2            ##STR978##                    ##STR979##                                   ##STR980##(I)-5-79 p-Cl    2            ##STR981##                    ##STR982##                                   ##STR983##(I)-5-80 m-OC6 H5         1            ##STR984##                    ##STR985##                                   ##STR986##(I)-5-81 m-OC6 H5         1            ##STR987##                    ##STR988##                                   ##STR989##(I)-5-82 m-OC6 H5         1            ##STR990##                    ##STR991##                                   ##STR992##(I)-5-83 m-OC6 H5         1            ##STR993##                    ##STR994##                                   ##STR995##(I)-5-84 m-OC6 H5         2            ##STR996##                    ##STR997##                                   ##STR998##(I)-5-85 m-OC6 H5         2            ##STR999##                    ##STR1000##                                   ##STR1001##(I)-5-86 m-OC6 H5         2            ##STR1002##                    ##STR1003##                                   ##STR1004##(I)-5-87 m-OC6 H5         2            ##STR1005##                    ##STR1006##                                   ##STR1007##(I)-5-88 m-OC6 H5         2            ##STR1008##                    ##STR1009##                                   ##STR1010##(I)-5-89 p-Cl    2            ##STR1011##                    ##STR1012##                                   ##STR1013##(I)-5-90 m-CH3         1            ##STR1014##                    ##STR1015##                                   ##STR1016##(I)-5-91 m-CH3         1            ##STR1017##                    ##STR1018##                                   ##STR1019##(I)-5-92 4-N(CH3)2         1            ##STR1020##                    ##STR1021##                                   ##STR1022##(I)-5-93 4-N(C2 H5)2         1            ##STR1023##                    ##STR1024##                                   ##STR1025##(I)-5-94  ##STR1026##         1            ##STR1027##                    ##STR1028##                                   ##STR1029##(I)-5-95  ##STR1030##         1            ##STR1031##                    ##STR1032##                                   ##STR1033##(I)-5-96  ##STR1034##         1            ##STR1035##                    ##STR1036##                                   ##STR1037##__________________________________________________________________________
In the photoconductors according to the present invention, at least one amino compound of the formula (I) is contained in the photoconductive layers 2a, 2b and 2c. The amino compounds can be employed in different ways, for example, as shown in FIG. 1, FIG. 2 and FIG. 3.
In the photoconductor as shown in FIG. 1, a photoconductive layer 2a is formed on an electroconductive support 1, which photoconductive layer 2a comprises an amino compound, a sensitizer dye and a binder agent. In this photoconductor, the amino compound works as a photoconductor material, through which charge carriers which are necessary for the light decay of the photoconductor are generated and transported. However, the amino compound itself scarcely absorbs light in the visible light range and, therefore, it is necessary to add a sensitizer dye which absorbs light in the visible light range in order to form latent electrostatic images by use of visible light.
Referring to FIG. 2, there is shown an enlarged cross-sectional view of another embodiment of an electrophotographic photoconductor according to the present invention. In the figure, reference numeral 1 indicates an electroconductive support. On the electroconductive support 1, there is formed a photoconductive layer 2b comprising a charge generating material 3 dispersed in a charge transporting medium 4 comprising an amino compound and a binder agent. In this embodiment, the amino compound works as a charge transporting material; and the amino compound and the binder agent in combination constitute the charge transporting medium 4. The charge generating material 3, which is, for example, an inorganic or organic pigment, generates charge carriers. The charge transporting medium 4 accepts the charge carriers generated by the charge generating material 3 and transports those charge carriers.
In this electrophotographic photoconductor, it is basically necessary that the light-absorption wavelength regions of the charge generating material 3 and the amino compound do not overlap in the visible light range. This is because, in order that the charge generating material 3 produce charge carriers efficiently, it is necessary that light pass through the charge transporting medium 4 and reach the surface of the charge generating material 3. Since the amino compounds of the above described general formula do not substantially absorb light in the visible range, they can work effectively as charge transporting materials in combination with the charge generating material 3 which absorbs the light in the visible region and generates charge carriers.
Referring to FIG. 3, there is shown an enlarged cross-sectional view of a further embodiment of an electrophotographic photoconductor according to the present invention. In the figure, there is formed on the electroconductive support 1 a two-layered photoconductive layer 2c comprising a charge generating layer 5 consisting essentially of the charge generating material 3, and a charge transporting layer 6 containing an amino compound of the previously described formula.
In this photoconductor, light which has passed through the charge transporting layer 6 reaches the charge generating layer 5, and charge carriers are generated within the charge generating layer 5. The charge carriers which are necessary for the light decay for latent electrostatic image formation are generated by the charge generating material 3 and accepted and transported by the charge transporting layer 6. In the charge transporting layer 6, the amino compound mainly works for transporting charge carriers. The generation and transportation of the charge carriers are performed by the same mechanism as that in the photoconductor shown in FIG. 2.
When an electrophotographic photoconductor according to the present invention as shown in FIG. 1 is prepared, at least one amino compound of the previously described formula (I) is dispersed in a binder resin solution, and a sensitizer dye is then added to the mixture, so that a photoconductive layer coating liquid is prepared. The thus prepared photoconductive layer coating liquid is coated on an electroconductive support 1 and dried, so that a photoconductive layer 2a is formed on the electroconductive support 1.
It is preferable that the thickness of the photosensitive layer 2a be in the range of 3 μm to 50 μm, more preferably in the range of 5 μm to 20 μm. It is preferable that the amount of the amino compound contained in the photoconductive layer 2a be in the range of 30 wt.% to 70 wt.% of the total weight of the photoconductive layer 2a, more preferably about 50 wt.% of the total weight of the photoconductive layer 2a. Further, it is preferable that the amount of the sensitizer dye contained in the photoconductive layer 2a be in the range of 0.1 wt.% to 5 wt.% of the total weight of the photoconductive layer 2a, more preferably in the range of 0.5 wt.% to 3 wt.%, of the total weight of the photoconductive layer 2a.
As the sensitizer dye, the following can be employed in the present invention: Triarylmethane dyes, such as Brilliant Green, Victoria Blue B, Methyl Violet, Crystal Violet, and Acid Violet 6B; xanthene dyes, such as Rhodamine B, Rhodamine 6G, Rhodamine G Extra, Eosin S, Erythrosin, Rose Bengale, and Fluorescein; thiazine dyes, such as Methylene Blue; cyanin dyes, such as cyanin; and pyrylium dyes, such as 2,6-diphenyl-4-(N,N-dimethylaminophenyl) thiapyrylium perchlorate and benzopyrylium salt (Japanese Patent Publication No. 48-25658). These sensitizer dyes can be used alone or in combination.
An electrophotographic photoconductor according to the present invention as shown in FIG. 2 can be prepared, for example, as follows. A charge generating material in the form of small particles is dispersed in a solution of one or more amino compounds and a binder agent. The thus prepared dispersion is coated on the electroconductive support 1 and is then dried, whereby a photoconductive layer 2b is formed on the electroconductive support 1.
It is preferable that the thickness of the photoconductive layer 2b be in the range of 3 μm to 50 μm, more preferably in the range of 5 μm to 20 μm. It is preferable that the amount of the amino compound contained in the photoconductive layer 2b be in the range of 10 wt.% to 95 wt.% of the total weight of the photoconductive layer 2b. Further, it is preferable that the amount of the charge generating material 3 contained in the photoconductive layer 2b be in the range of 0.1 wt.% to 50 wt.%, more preferably in the range of 1 wt.% to 20 wt.%, of the total weight of the photoconductive layer 2b.
As the charge generating material 3, the following can be employed in the present invention: Inorganic pigments, such as selenium, a selenium-tellurium alloy, cadmium sulfide, a cadmium sulfide - selenium alloy, and α-silicon; and organic pigments, for example, C.I. Pigment Blue 25 (C.I. 21180), C.I. Pigment Red 41 (C.I. 21200), C.I. Acid Red 52 (C.I. 45100), and C.I. Basic Red 3 (C.I. 45210); azo pigments having a carbazole skeleton (Japanese Laid-Open Patent Application No. 53-95033), azo pigments having a distyrylbenzene skeleton (Japanese Laid-Open Patent Application No. 53-133445), azo pigments having a triphenylamine skeleton (Japanese Laid-Open Patent Application No. 53-132347), azo pigments having a dibenzothiophene skeleton (Japanese Laid-Open Patent Application No. 54-21728), azo pigments having an oxazole skeleton (Japanese Laid-Open Patent Application No. 54-12742), azo pigments having a fluorenone skeleton (Japanese Laid-Open Patent Application No. 54-22834), azo pigments having a bisstilbene skeleton (Japanese Laid-Open Patent Application No. 54-17733), azo pigments having a distyryl oxadiazole skeleton (Japanese Laid-Open Patent Application No. 54-2129), azo pigments having a distyryl carbazole skeleton (Japanese Laid-Open Patent Application No. 54-14967); phthalocyanine-type pigments such as C.I. Pigment Blue 16 (C.I. 74100); Indigo-type pigments such as C.I. Vat Brown 5 (C.I. 73410) and C.I. Vat Dye (C.I. 73030); and perylene-type pigments, such as Algo Scarlet B (made by Bayer Co., Ltd.) and Indanthrene Scarlet R (made by Bayer Co., Ltd). These charge generating materials can be used alone or in combination.
An electrophotographic photoconductor according to the present invention as shown in FIG. 3 can be prepared, for example, as follows. A charge generating material 3 is vacuum-evaporated on the electroconductive support 1, whereby a charge generating layer 5 is formed. Alternatively, a charge generating material 3 in the form of fine particles is dispersed in a solution of a binder agent, and this dispersion is applied to the electroconductive support material 1 and then dried, and, if necessary, the applied layer is subjected to buffing to make the surface smooth or to adjust the thickness of the layer to a predetermined thickness, whereby a charge generating layer 5 is formed. A charge transporting layer 6 is then formed on the charge generating layer 5 by applying a solution of one or more amino compounds and a binder agent to the charge generating layer 5 and then drying. In this photoconductor, the charge generating material employed is the same as that employed in the photoconductor shown in FIG. 2.
It is preferable that the thickness of the charge generating layer 5 be 5 μm or less, more preferably 2 μm or less. It is preferable that the thickness of the charge transporting layer 6 be in the range of 3 μm to 50 μm, more preferably in the range of 5 μm to 20 μm. In the case where the charge generating layer 5 comprises a charge generating material in the form of fine particles, dispersed in a binder agent, it is preferable that the amount of the charge generating material in the charge generating layer 5 be in the range of 10 wt.% to 95 wt.% of the entire weight of the charge generating layer 5, more preferably in the range of about 50 wt.% to 90 wt.%. Further, it is preferable that the amount of the amino compound contained in the charge transporting layer 6 be in the range of 10 wt.% to 95 wt.%, more preferably in the range of 30 wt.% to 90 wt.% of the total weight of the charge transporting layer 6.
In the above described photoconductors according to the present invention, if necessary, an adhesive or barrier layer can be interposed between the electroconductive support material and the photoconductive layer. The adhesive layer or the barrier layer can be made of, for example, polyamide, nitrocellulose, or aluminum oxide. It is preferable that the thickness of the adhesive layer or barrier layer be 1 μm or less.
Preparation of Amino Compound (I)-1-6 in Table 1
10.42 g of 4-N,N-diphenylaminostilbene was dissolved in 100 ml of dioxane. To this solution, 1.04 g of a 5% palladium-carbon was added and the 4-N,N-diphenylaminostilbene in the mixture was hydrogenated with hydrogen at a pressure of 1 atm at 25� C. in a shaker hydrogenation apparatus. After the hydrogenation, the reaction mixture was filtered together with sellaite to obtain a filtrate. The filtrate was distilled under reduced pressure to remove dioxane therefrom, so that a colorless oily material was obtained. The oily material was chromatographed over silica gel - toluene, whereby 9.03 g of 4-phenethyltriphenylamine, which is a colorless viscous liquid, was obtained in a 86% yield.
The results of the elemental analysis of the thus obtained amino compound (I)-1-6, 4-phenethyltriphenylamine, were as follows:
______________________________________     % C        % H    % N______________________________________Found       89.27        6.61   4.02Calculated  89.34        6.65   4.01______________________________________
The above calculation was based on the formula for 4-phenethyltriphenylamine of C26 H23 N.
An infrared spectrum of the 4-phenethyltriphenylamine, taken by use of a KBr pellet, indicated the disappearance of the absorption based on the out-of-plane vibrations of the trans-olefin at 965 cm-1.
__________________________________________________________________________                                          Parts by__________________________________________________________________________                                          WeightDiane Blue (C.I. Pigment Blue 25,                76C.I. 21180) (a charge generatingpigment of the following formula (CG-1)) ##STR1038##2% tetrahydrofuran solution of                 1,260a polyester resin (Vylon 200made by Toyobo Co., Ltd.)Tetrahydrofuran                                3,700__________________________________________________________________________
This charge generating layer coating liquid was coated by a doctor blade on the aluminum-evaporated surface of an aluminum-evaporated polyester base film, which served as an electroconductive support, so that a charge generating layer, with a thickness of about 1 μm when dried at room temperature, was formed on the electroconductive support.
______________________________________                Parts by Weight______________________________________Amino Compound (I)-1-7 2in Table 1Polycarbonate resin (Panlite K 1300 made                  2by Teijin Limited.)Tetrahydrofuran        16______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade and dried at 80� C. for 2 minutes and then at 105� C. for 5 minutes, so that a charge transporting layer with a thickness of about 20 μm was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 1-1 according to the present invention was prepared.
The electrophotographic photoconductor No. 1-1 was charged negatively in the dark under application of -6 KV of corona charge for 20 seconds and then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, and the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=-920 V and E1/2 =2.9lux�seconds.
EXAMPLES 1-2 THROUGH 1-27
Example 1-1 was repeated except that the charge generating material and the amino compound which worked as the charge transporting material employed in Example 1-1 were respectively replaced by the charge generating materials and the amino compounds as listed in Table 6, whereby electrophotographic photoconductors No. 1-2 through No. 1-27 according to the present invention were prepared.
Vpo and E1/2 of those electrophotographic photoconductors were measured in the same manner as in Example 1-1. The results are shown in Table 7.
TABLE 6    Charge Trans-   porting Material Photo-  (Amino Compound Conductor Charge Generating Material in Table 1) No. 1-2  ##STR1039##  (I)-1-7  No. 1-3 ##STR1040##  (I)-1-7  No. 1-4 ##STR1041##  (I)-1-7  No. 1-5 ##STR1042##  (I)-1-7  No. 1-6 ##STR1043##  (I)-1-7  No. 1-7 &#946;                                                 type copper phthalocyanine (I)-1-7  No. 1-8 ##STR1044##  (I)-1-6  No. 1-9 CG-2 (I)-1-6 No. 1-10 CG-3 (I)-1-6 No. 1-11 CG-5 (I)-1-6 No. 1-12 CG-3  (I)-1-19 No. 1-13 CG-5  (I)-1-19 No. 1-14 CG-3 (I)-1-9 No. 1-15 CG-5 (I)-1-9 No. 1-16 CG-3  (I)-1-10 No. 1-17 CG-5 (I)-1-10 No. 1-18 CG-3 (I)-1-1 No. 1-19 CG-5 (I)-1-1 No. 1-20 CG-3 (I)-1-3 No. 1-21 CG-5 (I)-1-3 No. 1-22 CG-3  (I)-1-30 No. 1-23 CG-5 (I)-1-30 No. 1-24 CG-3  (I)-1-67 No. 1-25 CG-5  (I)-1-67 No. 1-26 CG-3 (I)-1-54 No. 1-27 CG-5  (I)-1-54
______________________________________                Parts by Weight______________________________________Amino Compound (I)-1-7 in Table 1                  2Polyester resin (Polyester Adhesive 49000                  3made by Du Pont Co.)Tetrahydrofuran        45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned selenium charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 1-28 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-720 V and E1/2 =3.0 lux�seconds.
A perylene pigment C.I. Vat Red 23 (C.I. 71130) of the following formula was vacuum-evaporated with a thickness of about 0.3 μm on an about 300 μm thick aluminum plate so that a charge generating layer was formed on the aluminum plate: ##STR1045##
______________________________________                Parts by Weight______________________________________Amino Compound (I)-1-6 in Table 1                  2Polyester resin (Polyester Adhesive 49000                  3made by Du Pont Co.)Tetrahydrofuran        45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 1-29 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-1240 V and E1/2 =3.2 lux�seconds.
One part by weight of Diane Blue (C.I. Pigment Blue 25, C.I. 21180) which was the same as that employed in Example 1-1 was added to 158 parts by weight of tetrahydrofuran, and the mixture was ground and dispersed in a ball mill. To this mixture, 12 parts by weight of the amino compound (I)-1-7 in Table 1 and 18 parts by weight of a polyester resin (Polyester Adhesive 49000 made by Du Pont Co.) were added and mixed, whereby a photoconductive layer coating liquid was prepared.
The thus prepared photoconductive layer coating liquid was coated on an aluminum-evaporated polyester film by a doctor blade and dried at 100� C. for 30 minutes, so that a photoconductive layer with a thickness of about 16 μm was formed on the aluminum-evaporated polyester film, thus, an electrophotographic photoconductor No. 1-30 according to the present invention was prepared.
The electrophotographic photoconductor No. 1-30 was charged positively in the dark under application of +6 kV of corona charge for 20 seconds and was then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, so that the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=+1350 V and E1/2 =2.9 lux�seconds.
The charge generating material, the charge transporting material, Vpo and E1/2 of each of the electrophotographic photoconductors No. 1-1 through No. 1-30 are summarized in the following Table 7:
TABLE 7______________________________________Photoconductor Vpo (volt)                    E1/2 (lux � sec)______________________________________ No. 1-1        -920     2.9 No. 1-2       -1250     2.6 No. 1-3       -830      1.2 No. 1-4       -1110     3.9 No. 1-5        -740     0.9 No. 1-6       -1010     1.1 No. 1-7        -730     2.1 No. 1-8       -1215     3.2 No. 1-9       -1000     2.7No. 1-10       -1210     1.3No. 1-11       -1100     0.7No. 1-12        -840     0.9No. 1-13        -920     0.8No. 1-14        -870     1.4No. 1-15        -955     1.5No. 1-16       -1200     0.8No. 1-17       -1100     0.6No. 1-18       -1310     1.7No. 1-19        -930     1.9No. 1-20       -1330     4.2No. 1-21       -1295     5.0No. 1-22        -925     1.7No. 1-23       -1000     0.9No. 1-24       -1105     0.7No. 1-25        -855     0.7No. 1-26        -720     1.3No. 1-27       -1010     1.1No. 1-28        -720     3.0No. 1-29       -1240     3.2No. 1-30       +1350     2.9______________________________________
Each of the electrophotographic photoconductors No. 1-1 through No. 1-29 prepared in Examples 1-1 through 1-29 was negatively charged, while the electrophotographic photoconductor No. 1-30 prepared in Example 1-30 was positively charged by a commercially available copying machine, so that a latent electrostatic image was formed on each photoconductor and developed with a dry type developer. The developed images were transferred to a high quality transfer sheet and were fixed to the transfer sheet. As a result, clear images were obtained from each of the electrophotographic photoconductors. Preparation of Amino Compound (I)-2-6 in Table 2
10.40 g of 1-(4-N,N-diphenylaminostyryl)naphthalene was dissolved in 100 ml of dioxane. To this solution, 1.04 g of a 5% palladium-carbon was added and 1-(4-N,N-diphenylaminophenethyl)naphthalene in the mixture was hydrogenated with hydrogen at a pressure of 1 atm at 25� C. in a shaker hydrogenation apparatus. After the hydrogenation, the reaction mixture was filtered together with sellaite to obtain a filtrate. The filtrate was distilled under reduced pressure to remove dioxane therefrom, so that a colorless oily material was obtained. The oily material was chromatographed over silica gel - toluene, whereby 9.02 g of 1-(4-N,N-diphenylaminophenethyl)naphthalene, which is a colorless viscous liquid, was obtained in a 86.3% yield.
The results of the elemental analysis of the thus obtained amino compound (I)-2-6, 1-(4-N,N-diphenylaminophenethyl)naphthalene, were as follows:
______________________________________     % C        % H    % N______________________________________Found       90.23        6.28   3.43Calculated  90.19        6.31   3.50______________________________________
The above calculation was based on the formula for 1-(4-N,N-diphenylaminostyryl)naphthalene of C30 H25 N.
An infrared spectrum of the 1-(4-N,N-diphenylaminophenethyl)naphthalene, taken by use of a KBr pellet, indicated the disappearance of the absorption based on the out-of-plane vibrations of the trans-olefin at 960 cm-1.
__________________________________________________________________________                                          Parts by__________________________________________________________________________                                          WeightDiane Blue (C.I. Pigment Blue 25,                76C.I. 21180) (a charge generatingpigment of the following formula (CG-1)) ##STR1046##2% tetrahydrofuran solution of                 1,260a polyester resin (Vylon 200made by Toyobo Co., Ltd.)Tetrahydrofuran                                3,700__________________________________________________________________________
______________________________________                Parts by Weight______________________________________Amino Compound (I)-2-9 2in Table 2Polycarbonate resin (Panlite K 1300 made                  2by Teijin Limited.)Tetrahydrofuran        16______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade and dried at 80� C. for 2 minutes and then at 105� C. for 5 minutes, so that a charge transporting layer with a thickness of about 20 μm was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 2-1 according to the present invention was prepared.
The electrophotographic photoconductor No. 2-1 was charged negatively in the dark under application of -6 kV of corona charge for 20 seconds and then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, and the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=-940 V and E1/2 =3.0 lux�seconds.
EXAMPLES 2-2 THROUGH 2-27
Example 2-1 was repeated except that the charge generating material and the amino compound which worked as the charge transporting material employed in Example 2-1 were replaced by the charge generating materials and the amino compounds, respectively, as listed in Table 8, whereby electrophotographic photoconductors No. 2-2 through No. 2-27 according to the present invention were prepared.
Vpo and E1/2 of those electrophotographic photoconductors were measured in the same manner as in Example 2-1. The results are shown in Table 9.
TABLE 8    Charge Trans-   porting Material Photo-  (Amino Compound Conductor Charge Generating Material in Table 2) No. 2-2  ##STR1047##  (I)-2-9  No. 2-3 ##STR1048##  (I)-2-9  No. 2-4 ##STR1049##  (I)-2-9  No. 2-5 ##STR1050##  (I)-2-9  No. 2-6 ##STR1051##  (I)-2-9  No. 2-7 &#946;                                                type copper phthalocyanine (I)-2-9  No. 2-8 ##STR1052##  (I)-2-12  No. 2-9 CG-2 (I)-2-12 No. 2-10 CG-3 (I)-2-12 No. 2-11 CG-5 (I)-2-12 No. 2-12 CG-3  (I)-2-102 No. 2-13 CG-5  (I)-2-102 No. 2-14 CG-3 (I)-2-33 No. 2-15 CG-5 (I)-2-33 No. 2-16 CG-3 (I)-2-6  No. 2-17 CG-5 (I)-2-6  No. 2-18 CG-3 (I)-2-51 No. 2-19 CG-5 (I)-2-51 No. 2-20 CG-3 (I)-2-49 No. 2-21 CG-5 (I)-2-49 No. 2-22 CG-3 (I)-2-93 No. 2-23 CG-5 (I)-2-93 No. 2-24 CG-3 (I)-2-89 No. 2-25 CG-5 (I)-2-89 No. 2-26 CG-3 (I)-2-98 No. 2-27 CG-5 (I)-2-98
______________________________________                Parts by Weight______________________________________Amino Compound (I)-2-9 in Table 2                  2Polyester resin (Polyester Adhesive 49000                  3made by Du Pont Co.)Tetrahydrofuran        45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned selenium charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 2-28 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-885 V and E1/2 =3.0 lux�seconds.
A perylene pigment C.I. Vat Red 23 (C.I. 71130) of the following formula was vacuum-evaporated with a thickness of about 0.3 μm on an about 300 μm thick aluminum plate so that a charge generating layer was formed on the aluminum plate: ##STR1053##
______________________________________                Parts by Weight______________________________________Amino Compound (I)-2-12 in Table 2                  2Polyester resin (Polyester Adhesive 49000                  3made by Du Pont Co.)Tetrahydrofuran        45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 2-29 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-1190 V and E1/2 =3.1 lux�seconds.
One part by weight of Diane Blue (C.I. Pigment Blue 25, C.I. 21180) which was the same as that employed in Example 2-1 was added to 158 parts by weight of tetrahydrofuran, and the mixture was ground and dispersed in a ball mill. To this mixture, 12 parts by weight of the amino compound (I)-2-9 in Table 2 and 18 parts by weight of a polyester resin (Polyester Adhesive 49000 made by Du Pont Co.) were added and mixed, whereby a photoconductive layer coating liquid was prepared.
The thus prepared photoconductive layer coating liquid was coated on an aluminum-evaporated polyester film by a doctor blade and dried at 100� C. for 30 minutes, so that a photoconductive layer with a thickness of about 16 μm was formed on the aluminum-evaporated polyester film, thus, an electrophotographic photoconductor No. 2-30 according to the present invention was prepared.
The electrophotographic photoconductor No. 2-30 was charged positively in the dark under application of +6 kV of corona charge for 20 seconds and was then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, so that the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=+1265 V and E1/2 =2.8 lux�seconds.
The charge generating material, the charge transporting material, Vpo and E1/2 of each of the electrophotographic photoconductors No. 1-1 through No. 1-30 are summarized in the following Table 9:
TABLE 9______________________________________Photoconductor Vpo (volt)                    E1/2  (lux � sec)______________________________________ No. 2-1        -940     3.0 No. 2-2       -1110     2.8 No. 2-3        -925     1.3 No. 2-4        -980     2.5 No. 2-5        -880     1.0 No. 2-6        -920     0.8 No. 2-7       -1025     1.1 No. 2-8       -1210     3.0 No. 2-9       -1170     2.5No. 2-10       -1090     1.2No. 2-11        -995     1.1No. 2-12       -1010     0.9No. 2-13        -950     1.2No. 2-14        -925     1.8No. 2-15       - 880     1.9No. 2-16        -930     2.0No. 2-17        -910     1.7No. 2-18       -1045     1.5No. 2-19       -1210     1.7No. 2-20        -985     1.5No. 2-21       -1050     1.8No. 2-22       -1210     1.1No. 2-23       -1190     0.9No. 2-24       -1205     0.9No. 2-25       -1170     1.1No. 2-26        -990     1.6No. 2-27       -1110     2.0No. 2-28        -885     3.0No. 2-29       -1190     3.1No. 2-30       +1265     2.8______________________________________
Each of the electrophotographic photoconductors No. 2-1 through No. 2-29 prepared in Examples 2-1 through 2-29 was negatively charged, while the electrophotographic photoconductor No. 2-30 prepared in Example 2-30 was positively charged by a commercially available copying machine, so that a latent electrostatic image was formed on each photoconductor and was developed with a dry type developer. The developed images were transferred to a high quality transfer sheet and were fixed to the transfer sheet. As a result, clear images were obtained from each of the electrophotographic photoconductors.
Preparation of Amino Compound (I)-3-2 in Table 3
11.00 g of 2-N,N-diphenylamino-5-styrylthiophene was dissolved in 100 ml of dioxane. To this solution, 1.10 g of a 5% palladium-carbon was added and the 2-N,N-diphenylamino-5-styrylthiophene in the mixture was hydrogenated with hydrogen at a pressure of 1 atm at 25� C. in a shaker hydrogenation apparatus. After the hydrogenation, the reaction mixture was filtered together with sellaite to obtain a filtrate. The filtrate was distilled under reduced pressure to remove dioxane therefrom, so that a colorless oily material was obtained. The oily material was chromatographed over silica gel - toluene, whereby 9.40 g of 2-N,N-diphenylamino-5-phenethylthiophene, which is a colorless viscous liquid, was obtained in a 85.4% yield.
The results of the elemental analysis of the thus obtained amino compound (I)-3-2, 2-N,N-diphenylamino-5phenethylthiophene, were as follows:
______________________________________      % C  % H        % N    % S______________________________________Found        81.13  5.92       3.96 8.98Calculated   81.08  5.96       3.94 9.02______________________________________
The above calculation was based on the formula for 2-N,N-diphenylamino-5-phenethylthiophene of C24 H21 NS.
An infrared spectrum of the 2-N,N-diphenylamino-5-phenethylthiophene, taken by use of a KBr pellet, indicated the disappearance of the absorption based on the out-of-plane vibrations of the trans-olefin at 945 cm-1.
__________________________________________________________________________                                          Parts by__________________________________________________________________________                                          WeightDiane Blue (C.I. Pigment Blue 25,                76C.I. 21180) (a charge generatingpigment of the following formula (CG-1)) ##STR1054##2% tetrahydrofuran solution of                 1,260a polyester resin (Vylon 200made by Toyobo Co., Ltd.)Tetrahydrofuran                                3,700__________________________________________________________________________
______________________________________                Parts by Weight______________________________________Amino Compound (I)-3-4 2in Table 3Polycarbonate resin (Panlite K 1300 made                  2by Teijin Limited.)Tetrahydrofuran        16______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade and dried at 80� C. for 2 minutes and then at 105� C. for 5 minutes, so that a charge transporting layer with a thickness of about 20 μm was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 3-1 according to the present invention was prepared.
The electrophotographic photoconductor No. 3-1 was charged negatively in the dark under application of -6 kV of corona charge for 20 seconds and then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, and the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=-925 V and E1/2 =2.4 lux�seconds.
EXAMPLES 3-2 THROUGH 3-27
Example 3-1 was repeated except that the charge generating material and the amino compound which worked as the charge transporting material employed in Example 3-1 were replaced by the charge generating materials and the amino compounds, respectively, as listed in Table 10, whereby electrophotographic photoconductors No. 3-2 through No. 3-27 according to the present invention were prepared.
Vpo and E1/2 of those electrophotographic photoconductors were measured in the same manner as in Example 3-1. The results are shown in Table 11.
TABLE 10    Charge Trans-   porting Material Photo-  (Amino Compound Conductor Charge Generating Material in Table 3) No. 3-2  ##STR1055##  (I)-3-4  No. 3-3 ##STR1056##  (I)-3-4  No. 3-4 ##STR1057##  (I)-3-4  No. 3-5 ##STR1058##  (I)-3-4  No. 3-6 ##STR1059##  (I)-3-4  No. 3-7 &#946;                                                type copper phthalocyanine (I)-3-4  No. 3-8 ##STR1060##  (I)-3-7   No. 3-9 CG-2 (I)-3-7  No. 3-10 CG-3 (I)-3-7  No. 3-11 CG-5 (I)-3-7  No. 3-12 CG-3 (I)-3-12 No. 3-13 CG-5 (I)-3-12 No. 3-14 CG-3 (I)-3-2  No. 3-15 CG-5 (I)-3-2  No. 3-16 CG-3 (I)-3-22 No. 3-17 CG-5 (I)-3-22 No. 3-18 CG-3 (I)-3-24 No. 3-19 CG-5 (I)-3-24 No. 3-20 CG-3 (I)-3-29 No. 3-21 CG-5 (I)-3-29 No. 3-22 CG-3 (I)-3-30 No. 3-23 CG-5 (I)-3-30 No. 3-24 CG-3 (I)-3-37 No. 3-25 CG-5 (I)-3-37 No. 3-26 CG-3 (I)-3-41 No. 3-27 CG-5 (I)-3-41
______________________________________                Parts by Weight______________________________________Amino Compound (I)-3-4 in Table 3                  2Polyester resin (Polyester Adhesive 49000                  3made by Du Pont Co.)Tetrahydrofuran        45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned selenium charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 3-28 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-1120 V and E1/2 =2.5 lux�seconds.
A perylene pigment C.I. Vat Red 23 (C.I. 71130) of the following formula was vacuum-evaporated with a thickness of about 0.3 μm on an about 300 μm thick aluminum plate so that a charge generating layer was formed on the aluminum plate: ##STR1061##
______________________________________               Parts by Weight______________________________________Amino Compound (I)-3-7 in Table 3                 2Polyester resin (Polyester Adhesive 49000                 3made by Du Pont Co.)Tetrahydrofuran       45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 3-29 according to the present invention was prepared
Vpo and E1/2 were measured. The results showed that Vpo =-920 V and E1/2 =3.0 lux�seconds.
One part by weight of Diane Blue (C.I. Pigment Blue 25, C.I. 21180) which was the same as that employed in Example 3-1 was added to 158 parts by weight of tetrahydrofuran, and the mixture was ground and dispersed in a ball mill. To this mixture, 12 parts by weight of the amino compound (I)-3-4 in Table 3 and 18 parts by weight of a polyester resin (Polyester Adhesive 49000 made by Du Pont Co.) were added and mixed, whereby a photoconductive layer coating liquid was prepared
The thus prepared photoconductive layer coating liquid was coated on an aluminum-evaporated polyester film by a doctor blade and dried at 100� C. for 30 minutes, so that a photoconductive layer with a thickness of about 16 μm was formed on the aluminum-evaporated polyester film, thus, an electrophotographic photoconductor No. 3-30 according to the present invention was prepared.
The electrophotographic photoconductor No. 3-30 was charged positively in the dark under application of +6 kV of corona charge for 20 seconds and was then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, so that the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=+860 V and E1/2 =2.4 lux�seconds.
The charge generating material, the charge transporting material, Vpo and E1/2 of each of the electrophotographic photoconductors No. 3-1 through No. 3-30 are summarized in the following Table 11:
TABLE 11______________________________________Photoconductor Vpo (volt)                    E1/2(lux � sec)______________________________________No. 3-1        -925      2.4No. 3-2        -760      2.8No. 3-3        -810      1.2No. 3-4        -625      2.1No. 3-5        -1100     0.9No. 3-6        -1290     1.1No. 3-7        -1015     1.4No. 3-8        -1150     2.0No. 3-9        -1120     2.9No. 3-10       -980      0.7No. 3-11       -1220     1.2No. 3-12       -1005     1.7No. 3-13       -925      1.8No. 3-14       -685      0.9No. 3-15       -960      1.2No. 3-16       -620      2.1No. 3-17       -1010     2.0No. 3-18       -790      1.5No. 3-19       -980      1.6No. 3-20       -1005     2.0No. 3-21       -965      2.2No. 3-22       -1250     1.5No. 3-23       -1040     1.4No. 3-24       -1005     0.9No. 3-25       -890      1.1No. 3-26       -560      1.3No. 3-27       -990      1.2No. 3-28       -1120     2.5No. 3-29       -920      3.0No. 3-30       +860      2.4______________________________________
Each of the electrophotographic photoconductors No. 3-1 through No. 3-29 prepared in Examples 3-1 through 3-29 was negatively charged, while the electrophotographic photoconductor No. 3-30 prepared in Example 3-30 was positively charged by a commercially available copying machine, so that a latent electrostatic image was formed on each photoconductor and was developed with a dry type developer. The developed images were transferred to a high quality transfer sheet and were fixed to the transfer sheet. As a result, clear images were obtained from each of the electrophotographic photoconductors. Preparation of Amino Compound (I)-4-27 in Table 4
13.5 g of α-phenyl-4'-N,N-di(4-trylamino)stilbene was dissolved in 100 ml of dioxane. To this solution, 1.35 g of a 5% palladium-carbon was added and the α-phenyl-4'-N,N-di(4-trylamino)stilbene in the mixture was hydrogenated with hydrogen at a pressure of 1 atm at 25� C. in a shaker hydrogenation apparatus. After the hydrogenation, the reaction mixture was filtered together with sellaite to obtain a filtrate. The filtrate was distilled under reduced pressure to remove dioxane therefrom, so that a colorless oily material was obtained. The oily material was chromatographed over silica gel - toluene, whereby 12.3 g of 4,4'-ditryl-4"-(β-phenylphenethyl)tryphenylamine, which is a colorless viscous liquid, was obtained in a 91% yield.
The results of the elemental analysis of the thus obtained amino compound (I)-4-27, di(4-trylamine)stilbene, were as follows:
______________________________________    % C         % H    % N______________________________________Found      89.92         6.91   3.11Calculated 90.01         6.90   3.09______________________________________
The above calculation was based on the formula for 4,4'-ditryl-4"-(β-phenylamino)stilbene of C34 H31 N.
An infrared spectrum of the 4,4'-ditryl-4"-(β-phenylphenethyl)triphenylamine, taken by use of a KBr pellet, indicated the disappearance of the absorption based on the out-of-plane vibrations of the trans-olefin at 960 cm-1.
__________________________________________________________________________                                            Parts by__________________________________________________________________________                                            WeightDiane Blue (C.I. Pigment Blue 25,                76C.I. 21180) (a charge generatingpigment of the following formula (CG-1)) ##STR1062##2% tetrahydrafuran solution of                   1,260a polyester resin (Vylon 200made by Toyobo Co., Ltd.)Tetrahydrafuran                                  3,700__________________________________________________________________________
______________________________________               Parts by Weight______________________________________Amino Compound (I)-4-27                 2in Table 4Polycarbonate resin (Panlite K 1300 made                 2by Teijin Limited.)Tetrahydrofuran       16______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade and dried at 80� C. for 2 minutes and then at 105� C. for 5 minutes, so that a charge transporting layer with a thickness of about 20 μm was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 4-1 according to the present invention was prepared.
The electrophotographic photoconductor No. 1-1 was charged negatively in the dark under application of -6 kV of corona charge for 20 seconds and then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, and the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=-930 V and E1/2 =3.8 lux�seconds.
EXAMPLES 4-2 THROUGH 4-27
Example 4-1 was repeated except that the charge generating material and the amino compound which worked as the charge transporting material employed in Example 4-1 were respectively replaced by the charge generating materials and the amino compounds as listed in Table 12, whereby electrophotographic photoconductors No. 4-2 through No. 4-27 according to the present invention were prepared.
Vpo and E1/2 of those electrophotographic photoconductors were measured in the same manner as in Example 4-1. The results are shown in Table 13.
TABLE 12    Charge Trans-   porting Material Photo-  (Amino Compound Conductor Charge Generating Material in Tables 4 &amp; 5) No. 4-2  ##STR1063##  (I)-4-27   No. 4-3  ##STR1064##  (I)-4-27   No. 4-4  ##STR1065##  (I)-4-27   No. 4-5  ##STR1066##  (I)-4-27   No. 4-6  ##STR1067##  (I)-4-27   No. 4-7   &#946;                                              type copper phthalocyanine (I)-4-27  No. 4-8  ##STR1068##  (I)-4-26   No. 4-9  CG-2 (I)-4-26 No. 4-10 CG-3 (I)-4-26 No. 4-11 CG-5 (I)-4-26 No. 4-12 CG-3 (I)-4-32 No. 4-13 CG-5 (I)-4-32 No. 4-14 CG-3 (I)-4-28 No. 4-15 CG-5 (I)-4-28 No. 4-16 CG-3 (I)-4-6  No. 4-17 CG-5 (I)-4-6  No. 4-18 CG-3 (I)-4-5  No. 4-19 CG-5 (I)-4-5  No. 4-20 CG-3 (I)-4-3  No. 4-21 CG-5 (I)-4-3  No. 4-22 CG-3 (I)-4-43 No. 4-23 CG-5 (I)-5-2  No. 4-24 CG-3 (I)-4-19 No. 4-25 CG-5 (I)-4-19 No. 4-26 CG-3 (I)-4-47 No. 4-27 CG-5 (I)-4-47
______________________________________               Parts by Weight______________________________________Amino Compound (I)-4-27 in Table 4                 2Polyester resin (Polyester Adhesive 49000                 3made by Du Pont Co.)Tetrahydrofuran       45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned selenium charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 4-28 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-1290 V and E1/2 =3.9 lux�seconds.
A perylene pigment C.I. Vat Red 23 (C.I. 71130) of the following formula was vacuum-evaporated with a thickness of about 0.3 μm on an about 300 μm thick aluminum plate so that a charge generating layer was formed on the aluminum plate: ##STR1069##
______________________________________               Parts by Weight______________________________________Amino Compound (I)-4-26 in Table 4                 2Polyester resin (Polyester Adhesive 49000                 3made by Du Pont Co.)Tetrahydrofuran       45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 4-29 according to the present invention was prepared.
Vpo and E1/2 were measured The results showed that Vpo =-1010 V and E1/2 =2.9 lux�seconds.
One part by weight of Diane Blue (C.I. Pigment Blue 25, C.I. 21180) which was the same as that employed in Example 4-1 was added to 158 parts by weight of tetrahydrofuran, and the mixture was ground and dispersed in a ball mill. To this mixture, 12 parts by weight of the amino compound (I)-4-27 in Table 4 and 18 parts by weight of a polyester resin (Polyester Adhesive 49000 made by Du Pont Co.) were added and mixed, whereby a photoconductive layer coating liquid was prepared.
The thus prepared photoconductive layer coating liquid was coated on an aluminum-evaporated polyester film by a doctor blade and dried at 100� C. for 30 minutes, so that a photoconductive layer with a thickness of about 16 μm was formed on the aluminum-evaporated polyester film, thus, an electrophotographic photoconductor No. 4-30 according to the present invention was prepared.
The electrophotographic photoconductor No. 4-30 was charged positively in the dark under application of +6 kV of corona charge for 20 seconds and was then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, so that the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=+1280 V and E1/2 =5.1 lux�seconds.
The charge generating material, the charge transporting material, Vpo and E1/2 of each of the electrophotographic photoconductors No. 4-1 through No. 4-30 are summarized in the following Table 13:
TABLE 13______________________________________Photoconductor Vpo (volts)                    E1/2 (lux � sec)______________________________________No. 4-1         -930     3.8No. 4-2        -1320     2.3No. 4-3        -1025     1.0No. 4-4        -1220     4.0No. 4-5         -985     0.9No. 4-6         -940     2.1No. 4-7         -735     3.1No. 4-8        -1210     4.2No. 4-9         -890     1.7No. 4-10       -1210     1.0No. 4-11       -1040     0.6No. 4-12       -1250     2.1No. 4-13       -1050     4.3No. 4-14       -1120     0.7No. 4-15        -910     0.8No. 4-16       -1320     2.0No. 4-17        -985     1.8No. 4-18       -1000     1.9No. 4-19       -1310     3.1No. 4-20       -1110     1.1No. 4-21        -765     1.3No. 4-22        -680     0.5No. 4-23        -430     0.7No. 4-24        -970     0.9No. 4-25        -830     0.8No. 4-26       -1250     1.2No. 4-27       -1000     1.0No. 4-28       -1290     3.9No. 4-29       -1010     2.9No. 4-30       +1280     5.1______________________________________
Each of the electrophotographic photoconductors No. 4-1 through No. 4-29 prepared in Examples 4-1 through 4-29 was negatively charged, while the electrophotographic photoconductor No. 4-30 prepared in Example 4-30 was positively charged by a commercially available copying machine, so that a latent electrostatic image was formed on each photoconductor and was developed with a dry type developer. The developed images were transferred to a high quality transfer sheet and were fixed to the transfer sheet. As a result, clear images were obtained from each of the electrophotographic photoconductors. Preparation of Amino Compound (I)-5-13 in Table 5
3.91 g of 1-phenyl-4-[4-N,N-bis(4-methylphenyl)amino]phenyl-1,3-butadiene was dissolved in 100 ml of dioxane. To this solution, 0.20 g of a 5% palladium-carbon was added and the 1-phenyl-4-[4,N,N-bis(4-methylphenyl)amino]phenyl-1,3-butadiene in the mixture was hydrogenated at a pressure of 1 atm at 25� C. in a shaker hydrogenation apparatus. After the hydrogenation, the reaction mixture was filtered together with sellaite to obtain a filtrate. The filtrate was distilled under reduced pressure to remove dioxane therefrom, so that white crystals were obtained. The white crystals were recrystallized from ethanol, whereby 2.60 g of 1-phenyl-4-[4-N,N-bis(4-methylphenyl)amino]phenylbutane was obtained in the form of white needles in a 86% yield, with a melting point of 52.0�-53� C.
The results of the elemental analysis of the thus obtained amino compound (I)-5-13 were as follows:
______________________________________    % C         % H    % N______________________________________Found      89.00         7.64   3.66Calculated 88.83         7.72   3.45______________________________________
The above calculation was based on the formula for 4-phenethyltriphenylamine of C30 H31 N.
An infrared spectrum of the 1-phenyl-4-[4-N,N-bis(4methylphenyl)amino]phenylbutane, taken by use of a KBr pellet, indicated the disappearance of the absorption at 990 cm-1, based on the out-of-plane vibrations of the butadiene, which is the starting material of this product.
__________________________________________________________________________                                            Parts by__________________________________________________________________________                                            WeightDiane Blue (C.I. Pigment Blue 25,                76C.I. 21180) (a charge generatingpigment of the following formula (CG-1)) ##STR1070##2% tetrahydrafuran solution of                   1,260a polyester resin (Vylon 200made by Toyobo Co., Ltd.)Tetrahydrafuran                                  3,700__________________________________________________________________________
______________________________________               Parts by Weight______________________________________Amino Compound (I)-5-13                 2in Table 5Polycarbonate resin (Panlite K 1300 made                 2by Teijin Limited.)Tetrahydrofuran       16______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade and dried at 80� C. for 2 minutes and then at 105� C. for 5 minutes, so that a charge transporting layer with a thickness of about 20 μm was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 5-1 according to the present invention was prepared.
The electrophotographic photoconductor No. 5-1 was charged negatively in the dark under application of -6 kV of corona charge for 20 seconds and then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of the photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). The photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, and the exposure E1/2 (lux�seconds) required to B reduce the initial surface potential Vpo (V) to 1/2 the initial surface potential Vpo (V) was measured. The results showed that Vpo (V)=-1020 V and E1/2 =2.54 lux�seconds.
EXAMPLES 5-2 THROUGH 5-27
Example 5-1 was repeated except that the charge generating material and the amino compound which worked as the charge transporting material employed in Example 5-1 were respectively replaced by the charge generating materials and the amino compounds as listed in Table 14, whereby electrophotographic photoconductors No. 5-2 through No. 5-27 according to the present invention were prepared.
Vpo and E1/2 of those electrophotographic photoconductors were measured in the same manner as in Example 5-1. The results are shown in Table 14.
TABLE 14    Charge Trans-   porting Material Photo-  (Amino Compound Conductor Charge Generating Material in Table 5)   No. 5-2  ##STR1071##  (I)-5-13   No. 5-3  ##STR1072##  (I)-5-13   No. 5-4  ##STR1073##  (I)-5-13   No. 5-5  ##STR1074##  (I)-5-13   No. 5-6  ##STR1075##  (I)-5-13   No. 5-7   &#946;                                              type copper phthalocyanine (I)-5-13  No. 5-8  ##STR1076##  (I)-5-6   No. 5-9  CG-2 (I)-5-6  No. 5-10 CG-3 (I)-5-6  No. 5-11 CG-5 (I)-5-6  No. 5-12 CG-3 (I)-5-23 No. 5-13 CG-5 (I)-5-23 No. 5-14 CG-5 (I)-5-29 No. 5-15 CG-5 (I)-5-29 No. 5-16 CG-3 (I)-5-36 No. 5-17 CG-5 (I)-5-36 No. 5-18 CG-3 (I)-5-45 No. 5-19 CG-5 (I)-5-45 No. 5-20 CG-3 (I)-5-60 No. 5-21 CG-5 (I)-5-60 No. 5-22 CG-3 (I)-5-73 No. 5-23 CG-5 (I)-5-73 No. 5-24 CG-3 (I)-5-76 No. 5-25 Cg-5 (I)-5-76 No. 5-26 CG-3 (I)-5-85 No. 5-27 CG-5 (I)-5-85
______________________________________               Parts by Weight______________________________________Amino Compound (I)-5-13 in Table 5                 2Polyester resin (Polyester Adhesive 49000                 3made by Du Pont Co.)Tetrahydrofuran       45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned selenium charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor No. 5-28 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-944 V and E1/2 =2.95 lux�seconds.
A perylene pigment C.I. Vat Red 23 (C.I. 71130) of the following formula was vacuum-evaporated with a thickness of about 0.3 μm on an about 300 μm thick aluminum plate so that a charge generating layer was formed on the aluminum plate: ##STR1077##
______________________________________               Parts by Weight______________________________________Amino Compound (I)-5-6 in Table 5                 2Polyester resin (Polyester Adhesive 49000                 3made by Du Pont Co.)Tetrahydrofuran       45______________________________________
The thus prepared charge transporting layer coating liquid was coated on the aforementioned charge generating layer by a doctor blade, dried at room temperature and then dried under reduced pressure, so that a charge transporting layer about 10 μm thick was formed on the charge generating layer; thus, an electrophotographic photoconductor (I)-1-29 according to the present invention was prepared.
Vpo and E1/2 were measured. The results showed that Vpo =-1066 V and E1/2 =2.77 lux�seconds.
One part by weight of Diane Blue (C.I. Pigment Blue 25, C.I. 21180) which was the same as that employed in Example 5-1 was added to 158 parts by weight of tetrahydrofuran, and the mixture was ground and dispersed in a ball mill. To this mixture, 12 parts by weight of the amino compound (I)-5-13 in Table 5 and 18 parts by weight of a polyester resin (Polyester Adhesive 49000 made by Du Pont Co.) were added and mixed, whereby a photoconductive layer coating liquid was prepared.
The thus prepared photoconductive layer coating liquid was coated on an aluminum-evaporated polyester film by a doctor blade and dried at 100� C. for 30 minutes, so that a photoconductive layer with a thickness of about 16 μm was formed on the aluminum-evaporated polyester film, thus, an electrophotographic photoconductor No. 5-30 according to the present invention was prepared.
The following components were mixed and dissolved, so that a charge transporting layer coating liquid was prepared, which is the same charge transporting layer coating liquid as that employed in Example 5-1:
__________________________________________________________________________                                                Parts by__________________________________________________________________________                                                WeightBiaso Pigment (a charge generating                   13.5pigment of the following formula (CG-5)) ##STR1078##Polyvinyl butyral(Trademark "XYHL" made by            5.4Union Carbide Plastic Co., Ltd.)Tetrahydrofuran                                       680Ethyl cellosolve                                     1020__________________________________________________________________________
Then a methanol/n-buthanol solution of a polyamide resin (Trademark "CM-8000" made by Toray Industries, Inc.) was coated on the charge generating layer by spray coating and dried at 120� C. for 30 minutes, whereby a protective layer having a thickness of about 0.5 μm was formed on the charge generating layer. Thus an electrophotographic photoconductor No. 5-31 according to the present invention was prepared.
The electrophotographic photoconductors Nos. 5-30 and 5-31 were charged positively in the dark under application of +6 kV of corona charge for 20 seconds and then allowed to stand in the dark for 20 seconds without applying any charge thereto. At this moment, the surface potential Vpo (V) of each photoconductor was measured by a Paper Analyzer (Kawaguchi Electro Works, Model SP-428). Each photoconductor was then illuminated by a tungsten lamp in such a manner that the illuminance on the illuminated surface of the photoconductor was 20 lux, so that the exposure E1/2 (lux�seconds) required to reduce the initial surface potential Vpo to 1/2 the initial surface potential Vpo (V) was measured.
The Vpo and E1/2 of each of the electrophotographic photoconductors No. 5-1 through No. 5-31 are shown in the following Table 15:
TABLE 15______________________________________            Vpo                    E1/2Photoconductor   (Volt)  (lux sec)______________________________________No. 5-1          -1020   2.54No. 5-2          -1285   2.01No. 5-3          -1276   1.20No. 5-4          -1310   3.01No. 5-5          -1284   1.38No. 5-6          -1210   1.54No. 5-7           -982   2.10No. 5-8          -1266   3.24No. 5-9          -1296   2.58No. 5-10         -1327   1.31No. 5-11         -1298   1.40No. 5-12         -1141   1.30No. 5-13         -1082   1.38No. 5-14         -1282   1.54No. 5-15         -1244   1.66No. 5-16         -1291   1.43No. 5-17         -1151   1.54No. 5-18         -1042   1.44No. 5-19         -1011   1.57No. 5-20          -981   1.10No. 5-21          -962   1.15No. 5-22          -920   1.05No. 5-23          -886   1.22No. 5-24         -1280   2.05No. 5-25         -1196   1.94No. 5-26         -1367   1.78No. 5-27         -1296   1.79No. 5-28          -944   2.95No. 5-29         -1066   2.77No. 5-30         +1155   3.12No. 5-31         +1280   1.52______________________________________
Each of the electrophotographic photoconductors No. 5-1 through Nos. 5-29 prepared in Examples 5-1 through 5-29 was negatively charged, while the electrophotographic photoconductors No. 5-30 and No. 5-31 prepared in Examples 5-30 and 5-31 were positively charged by a commercially available copying machine, so that a latent electrostatic image was formed on each photoconductor and developed with a dry type developer. The developed images were transferred to a high quality transfer sheet and were fixed to the transfer sheet. As a result, clear images were obtained from each of the electrophotographic photoconductors.
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS4515883 *Mar 30, 1984May 7, 1985Ricoh Company, Ltd.Stilbene derivatives, distyryl derivatives and electrophotographic photoconductor comprising at least one of the derivativesUS4603097 *Aug 31, 1984Jul 29, 1986Ricoh Company, LimitedStyrene derivatives and electrophotographic photoconductor comprising one of the styrene derivatives* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS5158850 *Dec 13, 1990Oct 27, 1992Ricoh Company, Ltd.Polyether compounds and electrophotographic photoconductor comprising one polyether compoundUS5324605 *Jul 27, 1992Jun 28, 1994Mitsubishi Kasei CorporationElectrophotographic plate with an arylamine-containing photosensitive layerUS7183435Jul 28, 2005Feb 27, 2007Ricoh Company, Ltd.Triphenylene compound, method for makingUS7452640Jul 28, 2005Nov 18, 2008Ricoh Company, Ltd.Electrophotographic photoconductor for liquid development, image forming apparatus having the same, and image forming methodUS7855040Oct 29, 2007Dec 21, 2010Ricoh Company Limitedforming a photosensitive layer over an electroconductive substrate, then coating with liquids including an addition polymer to form a protective layer, irradiating with light to crosslink the layer and injecting the layer with charge transfer compounds* Cited by examinerClassifications U.S. Classification430/58.65, 430/58.5, 430/73International ClassificationG03G5/06Cooperative ClassificationG03G5/0629, G03G5/067, G03G5/0618, G03G5/0668, G03G5/0614European ClassificationG03G5/06B7, G03G5/06H2B, G03G5/06H2B2, G03G5/06B5B, G03G5/06D2D2Legal EventsDateCodeEventDescriptionSep 27, 2001FPAYFee paymentYear of fee payment: 12Sep 25, 1997FPAYFee paymentYear of fee payment: 8Nov 15, 1993FPAYFee paymentYear of fee payment: 4Mar 30, 1990ASAssignmentOwner name: RICOH COMPANY, LTD., JAPANFree format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:SHIMADA, TOMOYUKI;SASAKI, MASAOMI;HASHIMOTO, MITSURU;REEL/FRAME:005277/0152Effective date: 19900205RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services