Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Radiation-sensitive composition or product
Reexamination Certificate
2001-02-26
2001-11-20
Goodrow, John (Department: 1753)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Radiation-sensitive composition or product
C430S059400
Reexamination Certificate
active
06319645
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention is directed generally to photoconductive components, and more specifically, to imaging members containing triphenylamines, and which amines are, for example, of the Formula I illustrated herein and wherein, for example, two of the aryl groups are 3,4-dimethylphenyl and the third aryl is a different phenyl group with, for example, from about 1 to about 5 substituents inclusive of hydrogen, linear or branched alkyl with from about 2 to about 18 carbons such as, for example, methyl, ethyl, n-propyl, n-butyl isopropyl, sec-butyl, 2-methylbutyl, neopentyl, 2-ethylhexyl and the like, alkyl like cycloalkyl such as cyclopentyl, cyclohexyl, cyclooctyl or cyclododecyl, substituted alkyl such as, for example, 3-methyoxypropyl, 4-hydroxybutyl, aralkyl like benzyl and phenethyl, and wherein the molecular weight M
W
of the triphenylamine is, for example, from about 301 to about 600, and yet more specifically, is from about 357 to about 425 Daltons, which weight can enable a reduction in environmental contamination
wherein R
1
to R
5
each are, for example, independently hydrogen, alkyl, aryl, cycloalkyl, alkoxy substituted alkyl or aralkyl, and the like, wherein alkoxy and alkyl contain, for example, from about 1 to about 25 carbon atoms; cycloalkyl contains from about 3 to about 35 carbon atoms; and aryl contains, for example, from about 6 to about 30 carbon atoms.
The hole-transporting triphenylamines of the present invention in embodiments do not significantly absorb light at a wavelength of from about 390 to about 450 nanometers. For example, solutions of these amines in an organic solvent or in a polymer binder such as polystyrene, polyester or polycarbonate at a concentration of about 50 percent (weight to volume) exhibit about 99 percent or more light transmission through a path length of from about 10 to about 100 micrometers at 400 nanometers.
Examples of specific triphenylamines or anilines with, for example, from about 390 to about 450 nanometers absorption depending, for example, on the amount of amine present and other factors are illustrated by Formulas 2a to d.
The triphenylamines illustrated herein can be selected as a charge transport, especially hole transport component in photoconductive imaging members useful in electrophotographic imaging and printing, and more specifically, in imaging and printing systems including color systems wherein light exposures of about 390 to about 450 nanometers are selected, and wherein a blue laser or ROS is selected.
PRIOR ART
Generally, layered photoresponsive imaging members are described in a number of U.S. patents, such as U.S. Pat. No. 4,265,990, the disclosure of which is totally incorporated herein by reference, wherein there is illustrated an imaging member comprised of a photogenerating layer, and an aryl amine hole transport layer. Examples of photogenerating layer components include trigonal selenium, metal phthalocyanines, vanadyl phthalocyanines, and metal free phthalocyanines. Additionally, there is described in U.S. Pat. No. 3,121,006 a composite xerographic photoconductive member comprised of finely divided particles of a photoconductive inorganic compound dispersed in an electrically insulating organic resin binder. The binder materials disclosed in the '006 patent can comprise a material which is substantially incapable of transporting for any significant distance injected charge carriers generated by the photoconductive particles.
The selection of selected perylene pigments as photoconductive substances are also known. There is thus described in Hoechst European Patent Publication 0040402, DE3019326, filed May 21, 1980, the use of N,N′-disubstituted perylene-3,4,9,10-tetracarboxyldiimide pigments as photoconductive substances. Specifically, there is, for example, disclosed in this publication N,N′-bis(3-methoxypropyl)perylene-3,4,9,10-tetracarboxyldiimide dual layered negatively charged photoreceptors with spectral response in the wavelength region of 400 to 700 nanometers. A similar disclosure is presented in Ernst Gunther Schlosser,
Journal of Applied Photographic Engineering,
Vol. 4, No. 3, page 118 (1978). There are also disclosed in U.S. Pat. No. 3,871,882 photoconductive substances comprised of specific perylene-3,4,9,10-tetracarboxylic acid derivative dyestuffs. Also, there is specifically disclosed in this patent dual layer photoreceptors with perylene-3,4,9,10-tetracarboxylic acid diimide derivatives, which have spectral response in the wavelength region of from 400 to 600 nanometers. Further, in U.S. Pat. No. 4,555,463, the disclosure of which is totally incorporated herein by reference, there is illustrated a layered imaging member with a chloroindium phthalocyanine photogenerating layer. In U.S. Pat. No. 4,587,189, the disclosure of which is totally incorporated herein by reference, there is illustrated a layered imaging member with a nonhalogenated perylene pigment photogenerating component. Both of the aforementioned patents and a number of the following patents disclose an aryl amine component as a hole transport layer.
Moreover, there is disclosed in U.S. Pat. No. 4,419,427, the disclosure of this is totally incorporated herein by reference, electrographic recording media with a photosemiconductive double layer comprised of a first layer containing a charge carrier perylene diimide dye, and a second layer with one or more compounds which are charge transporting materials when exposed to light.
U.S. Pat. No. 4,419,427, the disclosure of which is totally incorporated herein by reference, discloses the use of dispersions of perylene bisimides, with bis(2,6-dichlorophenylimide) being a specific material, in binder resins as CGL (charge generating layers) layers in devices overcoated with a charge transporting layer such as a poly(vinylcarbazole) composition. U.S. Pat. No. 4,429,029, the disclosure of which is totally incorporated herein by reference, illustrates the use, in devices similar to those of the '427 patent, of bisimides and bisimidazo perylenes in which the perylene nucleus is halogenated to an extent where 45 to 75 percent of the perylene ring hydrogens have been replaced by halogen. U.S. Pat. No. 4,587,189, the disclosure of which is totally incorporated herein by reference, illustrates layered photoresponsive imaging members prepared with highly-loaded dispersions, vacuum evaporated thin coatings of cis- and trans-bis(benzimidazo)perylene (4a, X=1,2-phenylene) and other perylenes overcoated with hole transporting compositions comprised of a variety of N,N,N′,N′-tetraaryl4,4′-diaminobiphenyls. U.S. Pat. No. 4,937,164 illustrates the use of perylene bisimides and bisimidazo pigments in which the 1,12-and/or 6,7 position of the perylene nucleus is bridged by one or two sulfur atoms wherein the pigments in the CGL layers are either vacuum evaporated or dispersed in binder resins and a layer of tetraaryl biphenyl hole transporting molecules.
U.S. Pat. No. 4,517,270, the disclosure of which is totally incorporated herein by reference, illustrates bisimides with propyl, hydroxypropyl, methoxypropyl and phenethyl substituents (4a, R=CH
3
CH
2
CH
2
—, HOCH
2
CH
2
CH
2
—, CH
3
OCH
2
CH
2
CH
2
—, and C
6
H
5
CH
2
CH
2
—) which are black or dark primarily because of their crystal properties, and perylene pigments which are nuclearly substituted with anilino, phenylthio, or p-phenylazoanilino groups. Similarly, in U.S. Pat. Nos. 4,719,163 and 4,746,741, the disclosures of this are totally incorporated herein by reference, there are disclosed layered electrophotographic devices having a certain spectral response to beyond 675 nanometers.
Dimeric perylene bisimide pigments are also known. For example, U.S. Pat. No. 4,968,571, the disclosure of this is totally incorporated herein by reference, discloses dimers of the type shown in Formula 3 wherein R
1
and R
2
are phenethyl groups and X is 1,4-phenylene, and wherein the charge transport can be an aryl amine.
Formula 3. Illustrative Formula of Dimeri
Allen C. Geoffrey
Duff James M.
Murti Dasarao K.
Goodrow John
Palazzo E. O.
Xerox Corporation
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