Compositions – Radiation sensitive
Reexamination Certificate
2000-05-25
2002-10-15
Tucker, Philip (Department: 1712)
Compositions
Radiation sensitive
C546S037000, C430S059100, C252S582000
Reexamination Certificate
active
06464902
ABSTRACT:
COPENDING APPLICATION AND RELATED PATENTS
Illustrated in U.S. Pat. No. 6,162,571 are photoconductive imaging members containing unsymmetrical perylenes; in U.S. Pat. No. 5,645,965 there is illustrated photoconductive imaging members containing symmetrical dimeric perylenes, and in U.S. Pat. No. 5,683,842 there is illustrated photoconductive imaging members containing unsymmetrical dimer perylenes. The disclosures of each of the above copending application and U.S. patents are totally incorporated herein by reference.
Illustrated in U.S. Pat. No. 6,287,738, the disclosure of which is totally incorporated herein by reference, are photoconductive imaging members containing perylene composition mixtures.
The appropriate components of the above applications and patents, such as the substrate, perylenes, processes, charge transport and the like may be selected for the present invention in embodiments thereof.
BACKGROUND OF THE INVENTION
The present invention is directed generally to perylene mixtures of the following formulas, and photogenerating photoconductive members comprised of mixtures of environmentally acceptable, and substantially nontoxic, or nontoxic symmetrical perylene bisimide dimers of the Formula 1
which dimers are illustrated in U.S. Pat. No. 5,645,965, the disclosure of which is totally incorporated herein by reference, and wherein R is, for example, hydrogen, alkyl, cycloalkyl, oxaalkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl, and the like, and Formula 2
and wherein R
1
and R
2
is, for example, hydrogen, alkyl, cycloalkyl, substituted alkyl, aromatic, aryl, substituted aryl, aralkyl, substituted aralkyl, and the like, and wherein each of R
1
and R
2
is dissimilar, that is, each R represents a different group, for example one R can be alkyl, and R
2
can be aryl.
Alkyl includes linear and branched components with, for example, from 1 to about 25, and preferably from 1 to about 10 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, 2-methylbutyl, heptyl, octyl, decyl, and the like. Cycloalkyl includes homologous rings from, for example, cyclopropane to cyclododecane. Substituted alkyl groups contain substituents such as hydroxy, alkoxy, carboxy, cyano, dialkylamino and the like. Aryl includes components with, for example, from 6 to about 24 carbon atoms such as phenyl, naphthyl, biphenyl, terphenyl and the like. Substituted aryl groups contain, for example, one to five substituents, such as alkyl like methyl, or tertiary-butyl, halogen (fluoro, chloro, bromo, and iodo), hydroxy, alkoxy like methoxy, nitro, cyano and dimethylamino. Aralkyl includes components with from 7 to about 24 carbon atoms such as benzyl, phenethyl, fluorenyl and the like. Substituted aralkyl groups can contain the same substituents as the aforementioned aryl groups, and more specifically, for example, methyl, tertiary-butyl, halogen, hydroxy, methoxy, nitro and dialkylamino.
The mixtures of perylene dimers illustrated herein can be selected as a photoactive component in photoconductive imaging members selected for electrophotographic printing, organic solar cells, chemical sensors, electroluminescent photoconductive members and other solid state optoelectronic photoconductive members utilizing photoconductors. Moreover, in embodiments the mixed dimers can be selected as a colorant in polymeric composite materials such as plastics, xerographic toners, and the like. Furthermore, the mixed perylene dimer pigments can be highly colored and can be prepared with a variety of hues such as orange, red, magenta, maroon, brown, black, greenish black, and the like, depending, for example, on the R substituents.
With the present invention in embodiments, photoconductive imaging members with the mixed perylene dimer pigments obtained by coupling two or more dissimilar perylene monoimides together, preferably via a propylene group, may enable a number of advantages with respect, for example, to photoconductive imaging members with monomeric perylene pigments or with pure symmetrical dimeric perylene pigments described in U.S. Pat. No. 5,645,965, the disclosure of which is totally incorporated herein by reference, internally unsymmetrical dimers described in U.S. Pat. No. 5,683,842, the disclosure of which is totally incorporated herein by reference, and pure terminally unsymmetrical dimers of the type described in copending application U.S. Ser. No. 09/165,595. For example, as illustrated in Table 2 below, photoconductive members comprising a photogenerator layer prepared from the pure dimer of Formula 1 wherein R is n-pentyl evidences a photosensitivity E
{fraction (1/2 )}
of 2.85 ergs/cm
2
, the dimer corresponding to Formula 1 wherein R is 2-methylbutyl provided a sensitivity about 5.45 ergs/cm
2
and the pure, terminally unsymmetrical dimer corresponding to Formula 2 wherein R
1
is n-pentyl and R
2
is 2-methylbutyl indicated a sensitivity of 3.33 ergs/cm
2
, whereas, as will be illustrated hereinafter, a similar photoconductive member prepared from a mixture of dimers prepared by the condensation of a 60:40 mixture of the monoimide corresponding to Formula 3 with R=n-pentyl and the monoimide corresponding to Formula 3 illustrated hereinafter with R=2-methylbutyl with 1,3-diaminopropane, which condensation results in the formation of an intimate mixture comprised of about 36 percent of the dimer corresponding to Formula 1 with R=n-pentyl, 16 percent of the dimer corresponding to Formula 1 wherein R=2-methylbutyl and about 48 percent of the dimer corresponding to Formula 2 wherein R
1
=n-pentyl and R
2
=2-methylbutyl, had a photosensitivity E
½
=2.28 ergs/cm
2
.
In embodiments, the present invention is directed to photogenerating pigments comprised of mixtures of symmetrical perylene bisimide dimers and terminally-unsymmetrical perylene bisimide dimers; and to an imaging member comprised of a supporting substrate, a photogenerating layer comprised of a mixture of symmetrical perylene dimers of Formula 1 and unsymmetrical dimers of Formula 2, and more specifically, wherein R, R
1
and R
2
are selected from hydrogen, methyl, ethyl, n-propyl, 3-hydroxypropyl, 3-methoxypropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, neopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, phenyl, benzyl, 3-chlorobenzyl, phenethyl and the like, and a charge, especially hole, transport layer. Imaging members with the photogenerating pigments of the present invention are sensitive to wavelengths of, for example, from about 400 to about 700 nanometers, that is in the visible region of the light spectrum. Also, in embodiments thereof, the imaging members of the present invention generally possess broad spectral response to white light or, specifically to red, green and blue light emitting diodes and stable electrical properties over long cycling times. Many of the mixed perylene bisimide dimers of the present invention, when selected as photogenerator pigments, exhibit excellent charge acceptance of about a 800 volt surface potential in a layered photoconductive member, dark decay of, for example, less than about 100 volts per second, for example from about 40 to about 90, photosensitivities ranging from E
½
of less than about 3 to about 10 ergs, excellent dispersibility and low solubility in typical coating compositions, such as solutions of certain polymers in organic solvents, such as methylene chloride, toluene, cyclohexanone, tetrahydrofuran, chlorobenzene and butyl acetate, selected for the preparation of layered photoresponsive, or photoconductive imaging members. The mixed perylene dimers of the present invention can be selected as a substitute for selenium, such as trigonal selenium, in layered photoconductive imaging members, and further the imaging members of the present invention can be selected with red blue and green LED lasers for digital systems, and for upgraded visible light systems, and machines.
Also, the present invention in embodiments is directed to a
Allen C. Geoffrey
Duff James M.
Gaynor Roger E.
Hamer Gordon K.
Hor Ah-Mee
Palazzo E. O.
Tucker Philip
Xerox Corporation
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