This invention is generally directed to layered photoresponsive imaging members, and more specifically to photoconductive members comprised of perinone compounds and processes for the preparation thereof. In one embodiment of the present invention, there are provided organic photoconductive layered imaging members comprised of unsymmetrical perinones and charge or hole transport layers comprised of for example, aryl amines as illustrated in U.S. Pat. Nos. 4,265,990 and 4,925,760, the disclosures of which are totally incorporated herein by reference. Further, in one embodiment of the present invention there is provided a photoresponsive imaging member or device with panchromatic visible sensitivity comprised of unsymmetrical perinones of the formulas illustrated herein and the derivatives thereof, and an aryl amine hole transport layer. The photoresponsive imaging members of the present invention can be selected for various electrophotographic imaging and printing processes, especially xerographic processes wherein, for example, latent images are formed thereon followed by development and transfer to a suitable substrate.
Imaging members with symmetrical perinones are illustrated in U.S. Pat. No. 4,808,506, the disclosure of which is totally incorporated herein by reference.
In a patentability search report, there were listed as prior art the following U.S. patents: U.S. Pat. No. 3,879,200 relating to a xerographic plate with photoinjecting bis-benzimidazole pigments as illustrated in, for example, columns 3 and 4; U.S. Pat. No. 3,992,205 which discloses an electrophotographic recording material with a photoconductive multilayer system, see the Abstract of the Disclosure for example, and note formulas (1) to (9), and particularly formula 6 and column 8; U.S. Pat. No. 4,714,666 which discloses perylene tetracarboxylic acid amine pigments for electrophotographic recording systems, see for example the Abstract of the Disclosure; U.S. Pat. No. 4,725,520 directed to, for example, electrophotographic recording materials with certain benzo-benzimidazoquinoline derivatives of the formulas as illustrated in the Abstract of the Disclosure; U.S. Pat. No. 4,792,508, the disclosure of which is totally incorporated herein by reference, which discloses photoconductive layered imaging members with aryl diamine hole transports, see column 9, and as a photogenerating pigment cis, trans perylene isomers of the formula as illustrated in the Abstract of the Disclosure and in column 5; and as secondary interest U.S. Pat. Nos. 3,533,785; 3,877,935; 4,396,696; 4,419,427 and 4,469,769.
Illustrated in U.S. Pat. No. 4,315,981 are double layered electrophotographic recording materials with an electroconductive support and a photoconductive double layer of organic materials with a homogeneous opaque charge carrier producing dyestuff layer obtained from an annealed quinone, or the substitution product thereof selected from the group consisting of dibenzopyrene, quinone, anthraquinone, pyranthrone, dibenzanthrone, and flavanthrone, and a transparent top layer of an insulating material of at least one charge transporting compound. The transport layer contains a charge transporting monomer as reference, for example, in column 2, lines 37 to 56. Further, as indicated in column 4, lines 1 to 22, as the formula 9 compound for the imaging member of the '981 patent there can be selected dibromo-8,16-pyranthrenedione (Indanthrene Orange RRTS, C.I. 59,705). Moreover, it is indicated in column 4, beginning at around line 53, that the organic dyestuff layer may be applied by vapor depositing the dyestuff in a vacuum. Also, this patent discloses a number of resinous binders for the charge transport layer including polycarbonate resins, reference column 7. Further, in U.S. Pat. No. 3,871,882 there are disclosed layered electrophotographic recording materials containing an electroconductive support material and a photoconductive double layer of organic materials, reference for example the Abstract of the Disclosure. Other representative patents of background interest include U.S. Pat. Nos. 3,871,882 and 3,973,959.
In Konishiroku Kokai Japanese 59/184349/A2[84/184349], Oct. 19, 1984, there is disclosed the use of selected pyranthrones as charge generator layers in conjunction with hydrazone charge transport layers. Specifically, a solution coated dispersion of dibromo-8,16-pyranthrenedione in a polymer binder can be selected as the charge generator layer. Also, in U.S. Pat. No. 3,877,935 there are disclosed imaging members with dibromo-8,16-pyranthrenedione vacuum coated charge generator layers contiguous with poly(vinyl carbazole) charge transport layers.
Other prior art that may be of interest includes U.S. Pat. Nos. 4,028,102; 4,399,207; 4,454,211; 4,554,231 and 4,714,666. In the '102 patent, there are illustrated diamine condensation products in double layered photoconductive recording elements. More specifically, there are disclosed in the '102 patent condensation products of o-phenylamine diamine or 1,8-diaminonaphthalene and 4,10-benzothioxanthrene-3,1'-dicarboxylic anhydride of the formulas as illustrated in column 2, and of the formulas 1 to 5, reference column 3, beginning at line 55. The '207 patent discloses electrophotographic photosensitive members with hydrazone compounds of the formula, for example, as illustrated in the Abstract of the Disclosure and in column 2. Examples of charge generating layer materials are illustrated beginning in column 16, line 65, and include, for example, phthalocyanine pigments, perylene pigments, and the like, typical examples of which are specifically recited in columns 17 through 26. The '211 patent discloses electrophotographic photosensitive members with pyrazoline charge transport materials, see for example column 2, beginning at line 35. Specific organic photoconductive materials or charge transporting materials disclosed in the '211 patent are illustrated in columns 3 and 4, formulas 1 and 2, thereof. Charge generating layers for the photoconductive members in the '211 patent are illustrated in column 42, beginning at line 11, and include, for example, organic substances such as pyrylium dyes, thiopyrylium dyes, perylene pigments, and the like with specific examples of charge generating materials being illustrated in columns 42 to 52. Also, it is disclosed in column 57 that a charge generating layer can be formed on an aluminum plate by the vacuum deposition of a perylene pigment having carbon atom bridges at the 1, 12 and 6, 7 positions of the common perylene molecule. In U.S. Pat. No. 4,554,231, there is illustrated an electrophotosensitive member comprised of a layer containing a hydrazone compound of the formula, for example, as illustrated in the Abstract of the Disclosure, which hydrazone compound is selected as charge transport material, reference column 5, line 30, and wherein there are selected various charge generating layer materials including, for example, pyrylium dyes, thiopyrylium dyes, perylene pigments and the like, see column 6, beginning at line 23, and note particularly columns 7 through 12. The use of Vylon 200 on a charge generating layer is disclosed at column 19, lines 15 to 21. In the U.S. Pat. No. 4,714,666 there are illustrated perylene tetracarboxylic acid imide pigments in electrophotographic recording materials, which pigments include those, for example, as represented by the formula 1, reference the Abstract of the Disclosure.
Moreover, in U.S. Pat. No. 4,587,189, the disclosure of which is totally incorporated herein by reference, there are illustrated layered imaging members with photoconductive layers comprised of cis and transbis(benzimidazo)perylene pigments.
Additionally, numerous different xerographic photoconductive members are known including, for example, a homogeneous layer of a single material such as vitreous selenium, or a composite layered device containing a dispersion of a photoconductive composition. An example of one type of composite xerographic photoconductive member is described, for example, in U.S. Pat. No. 3,121,006 wherein there is disclosed finely divided particles of a photoconductive inorganic compound dispersed in an electrically insulating organic resin binder.
There are also known photoreceptor materials comprised of inorganic or organic materials wherein the charge carrier generating, and charge carrier transport functions are accomplished by discrete contiguous layers. Additionally, layered photoreceptor materials are disclosed in the prior art which include an overcoating layer of an electrically insulating polymeric material. Also, there have been disclosed other layered photoresponsive devices including those comprised of separate generating layers, and transport layers as described in U.S. Pat. No. 4,265,990, the disclosure of which is totally incorporated herein by reference. Examples of photogenerating layers that may be selected include trigonal selenium and phthalocyanines, while examples of transport layers include certain diamines as mentioned herein.
Many other patents are in existence describing photoresponsive devices including layered devices containing generating substances, such as U.S. Pat. No. 3,041,167 which discloses an overcoated imaging member containing a conductive substrate, a photoconductive layer, and an overcoating layer of an electrically insulating polymeric material. This member is utilized in an electrophotographic copying system by, for example, initially charging the member with an electrostatic charge of a first polarity, and imagewise exposing to form an electrostatic latent image, which can be subsequently developed to form a visible image.
Furthermore, there are illustrated in U.S. Pat. No. 4,232,102 and 4,233,383 photoresponsive imaging members comprised of trigonal selenium doped with sodium carbonate, sodium selenite, and trigonal selenium doped with barium carbonate, and barium selenite, or mixtures thereof. Moreover, there is disclosed in U.S. Pat. No. 3,824,099 certain photosensitive hydroxy squaraine compositions. According to the disclosure of this patent, the squaraine compositions are photosensitive in normal electrostatographic imaging systems.
In U.S. Pat. No. 4,508,803, the disclosure of which is totally incorporated herein by reference, there is described an improved photoresponsive device comprised of a supporting substrate, a hole blocking layer, an optional adhesive interface layer, an inorganic photogenerating layer, a photoconducting composition layer comprised of benzyl fluorinated squaraine compositions, and a hole transport layer. Other representative patents disclosing photoconductive devices with squaraine components therein include U.S. Pat. No. 4,507,408; 4,552,822; 4,559,286; 4,507,480; 4,524,220; 4,524,219; 4,524,218; 4,525,592; 4,559,286; 4,415,639; 4,471,041 and 4,486,520. The disclosures of each of the aforementioned patents are totally incorporated herein by reference.
Furthermore, disclosed in the prior art are composite electrophotographic photosensitive materials with various azo compounds. For example, there are illustrated in Japanese Ricoh Patent Publication 6064354, published Apr. 12, 1985, composite photoconductors wherein one of the photoconductor layers contains an azo compound of the formulas as illustrated. Further, there are illustrated in several U.S. patents and publications layered organic electrophotographic photoconductor elements with azo, bisazo, or related compounds. Examples of these patents and publications include U.S. Pat. No. 4,400,455; 4,551,404; 4,390,608; 4,327,168; 4,299,896; 4,314,015; 4,486,522; 4,486,519 and 4,551,404; and Konishiroku Japanese Patent Laid Open Publication 60111247.
Other prior art that may be of background interest includes Japanese Patent 59-59686; Japanese Patent 59-154454; European Patent 100,581; U.S. Pat. No. 4,578,334; European Patent 40,402; U.S. Pat. No. 4,431,721; German Patent 3,110,954; R. O. Loutfy, Can. J. Chem 59,544, (1981); and F. Graser and E. Hadicke, Liebigs Ann. Chem., 483 (1984).
Although photoconductive imaging members are known, there remains a need for members with other photogenerator layers. Additionally, there continues to be a need for layered photoresponsive imaging members having incorporated therein perinone compounds, which members will enable the generation of acceptable high quality images and wherein these members can be repeatedly used in a number of imaging cycles without deterioration thereof from the machine environment or surrounding conditions. Moreover, there is a need for improved layered photoresponsive imaging members wherein there is selected as the photogenerator unsymmetrical perinones preferably in contact with specific aryl amine charge transport compositions, which members are sensitive to wavelengths of light of from about 400 to about 700 nanometers. Additionally, there is a need for layered photoconductors with unsymmetrical perinone compounds, which photoconductors are of high sensitivity, that is they posses in an embodiment of the present invention a peak photosensitivity at 550 nanometers of better than 10 ergs/cm.sup.2 when calculated with respect to E.sub.1/2 values (less than 4 ergs/cm.sup.2 is preferred), and have low dark decay values of from 0 to about 100 volts, and preferably less than 50 volts/second, low residual potentials of, for example, less than about 100 volts, and possess high cyclic stability, that is for example stable electricals for more than 20,000 imaging cycles, and are robost. Furthermore, there continues to be a need for photoresponsive imaging members which can be positively or negatively charged thus permitting the development of images, including color images with positively or negatively charged toner compositions. Also, there is a need for disposable imaging members useful in xerographic imaging processes, and xerographic printing systems wherein, for example, light emitting diodes (LED), helium-cadmium or helium-neon lasers, can be selected; and wherein these members are particularly sensitive to the visible region of the spectrum, that is from about 400 to about 700 nanometers. Further, there is a need for processes that will enable the preparation of unsymmetrical perinones with, for example, relatively high volatility and acceptable photosensitivity, which have been heretobefore been inaccessible, it is believed, as attempts to prepare these compounds usually results to the formation of mixtures of symmetrical compounds and the starting anhydride reactant.
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