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  Organic photosensitive devices using subphthalocyanine compoundsUSPTO Application #: 20070272918Title: Organic photosensitive devices using subphthalocyanine compounds Abstract: An organic photosensitive optoelectronic device, having a donor-acceptor heterojunction of a donor-like material and an acceptor-like material and methods of making such devices is provided. At least one of the donor-like material and the acceptor-like material includes a subphthalocyanine, a subporphyrin, and/or a subporphyrazine compound; and/or the device optionally has at least one of a blocking layer or a charge transport layer, where the blocking layer and/or the charge transport layer includes a subphthalocyanine, a subporphyrin, and/or a subporphyrazine compound. (end of abstract) Agent: Kenyon & Kenyon LLP - New York, NY, US Inventors: Barry Rand, Stephen R. Forrest, Kristin L. Mutolo, Elizabeth Mayo, Mark E. Thompson USPTO Applicaton #: 20070272918 - Class: 257040000 (USPTO) Related Patent Categories: Active Solid-state Devices (e.g., Transistors, Solid-state Diodes), Organic Semiconductor Material The Patent Description & Claims data below is from USPTO Patent Application 20070272918. Brief Patent Description - Full Patent Description - Patent Application Claims
JOINT RESEARCH AGREEMENT [0002] The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university-corporation research agreement: Princeton University, The University of Southern California, The University of Michigan, and Global Photonic Energy Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement. FIELD OF THE INVENTION [0003] The present invention generally relates to organic photosensitive optoelectronic devices. More specifically, it is directed to organic photosensitive optoelectronic devices having a donor acceptor heterojunction, comprising a donor-like material and an acceptor-like material, at least one of the donor-like material and the acceptor-like material comprises a subphthalocyanine, subporphyrin, and/or subporphyrazine material; and/or the device optionally comprises at least one of a blocking layer or a charge transport layer, wherein the blocking layer and/or the charge transport layer comprises a subphthalocyanine, a subporphyrin, and/or a subporphyrazine compound. BACKGROUND OF THE INVENTION [0004] Optoelectronic devices rely on the optical and electronic properties of materials to either produce or detect electromagnetic radiation electronically or to generate electricity from ambient electromagnetic radiation. [0005] Photosensitive optoelectronic devices convert electromagnetic radiation into an electrical signal or electricity. Solar cells, also called photovoltaic ("PV") devices, are a type of photosensitive optoelectronic device that is specifically used to generate electrical power. Photoconductor cells are a type of photosensitive optoelectronic device that are used in conjunction with signal detection circuitry which monitors the resistance of the device to detect changes due to absorbed light. Photodetectors, which may receive an applied bias voltage, are a type of photosensitive optoelectronic device that are used in conjunction with current detecting circuits which measures the current generated when the photodetector is exposed to electromagnetic radiation. [0006] These three classes of photosensitive optoelectronic devices may be distinguished according to whether a rectifying junction as defined below is present and also according to whether the device is operated with an external applied voltage, also known as a bias or bias voltage. A photoconductor cell does not have a rectifying junction and is normally operated with a bias. A PV device has at least one rectifying junction and is operated with no bias. A photodetector has at least one rectifying junction and is usually but not always operated with a bias. [0007] As used herein, the term "rectifying" denotes, inter alia, that an interface has an asymmetric conduction characteristic, i.e., the interface supports electronic charge transport preferably in one direction. The term "semiconductor" denotes materials which can conduct electricity when charge carriers are induced by thermal or electromagnetic excitation. The term "photoconductive" generally relates to the process in which electromagnetic radiant energy is absorbed and thereby converted to excitation energy of electric charge carriers so that the carriers can conduct (i.e., transport) electric charge in a material. The term "photoconductive material" refers to semiconductor materials which are utilized for their property of absorbing electromagnetic radiation to generate electric charge carriers. As used herein, "top" means furthest away from the substrate, while "bottom" means closest to the substrate. There may be intervening layers, unless it is specified that the first layer is "in physical contact with" the second layer. [0008] When electromagnetic radiation of an appropriate energy is incident upon an organic semiconductor material, a photon can be absorbed to produce an excited molecular state. In organic photoconductive materials, the generated molecular state is generally believed to be an "exciton," i.e., an electron-hole pair in a bound state which is transported as a quasi-particle. An exciton can have an appreciable life-time before geminate recombination ("quenching"), which refers to the original electron and hole recombining with each other (as opposed to recombination with holes or electrons from other pairs). To produce a photocurrent, the electron-hole forming the exciton is typically separated at a rectifying junction. [0009] In the case of photosensitive devices, the rectifying junction is referred to as a photovoltaic heterojunction. Types of organic photovoltaic heterojunctions include a donor-acceptor heterojunction formed at an interface of a donor material and an acceptor material, and a Schottky-barrier heterojunction formed at the interface of a photoconductive material and a metal. [0010] FIG. 1 is an energy-level diagram illustrating an example donor-acceptor heterojunction. In the context of organic materials, the terms "donor" and "acceptor" refer to the relative positions of the Highest Occupied Molecular Orbital ("HOMO") and Lowest Unoccupied Molecular Orbital ("LUMO") energy levels of two contacting but different organic materials. If the LUMO energy level of one material in contact with another is lower, then that material is an acceptor. Otherwise it is a donor. It is energetically favorable, in the absence of an external bias, for electrons at a donor-acceptor junction to move into the acceptor material. [0011] As used herein, a first HOMO or LUMO energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level 10. A higher HOMO energy level corresponds to an ionization potential ("IP") having a smaller absolute energy relative to a vacuum level. Similarly, a higher LUMO energy level corresponds to an electron affinity ("EA") having a smaller absolute energy relative to vacuum level. On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. [0012] After absorption of a photon 6 in the donor 152 or the acceptor 154 creates an exciton 8, the exciton 8 disassociates at the rectifying interface. The donor 152 transports the hole (open circle) and the acceptor 154 transports the electron (dark circle). [0013] A significant property in organic semiconductors is carrier mobility. Mobility measures the ease with which a charge carrier can move through a conducting material in response to an electric field. In the context of organic photosensitive devices, a material that conducts preferentially by electrons due to a high electron mobility may be referred to as an electron transport material. A material that conducts preferentially by holes due to a high hole mobility may be referred to as a hole transport material. A layer that conducts preferentially by electrons, due to mobility and/or position in the device, may be referred to as an electron transport layer ("ETL"). A layer that conducts preferentially by holes, due to mobility and/or position in the device, may be referred to as a hole transport layer ("HTL"). Preferably, but not necessarily, an acceptor material is an electron transport material and a donor material is a hole transport material. [0014] How to pair two organic photoconductive materials to serve as a donor and an acceptor in a photovoltaic heterojunction based upon carrier mobilities and relative HOMO and LUMO levels is well known in the art, and is not addressed here. [0015] As used herein, the term "organic" includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule" class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a "small molecule." In general, a small molecule has a defined chemical formula with a molecular weight that is the same from molecule to molecule, whereas a polymer has a defined chemical formula with a molecular weight that may vary from molecule to molecule. As used herein, "organic" includes metal complexes of hydrocarbyl and heteroatom-substituted hydrocarbyl ligands. [0016] Padinger, et al., Adv. Funct. Mater., 2003, 13, 85-88, reported photovoltaic cells, comprising polymer-fullerene heterojunctions that reportedly had power conversion efficiencies averaging 3 to 4 percent. Efficiencies approaching 5 percent were reportedly also obtained through variations in the processing techniques. Efficiencies as high as 4 percent under 4 suns simulated AM1.5G illumination in a double-heterostructure copper phthalocyanine (CuPc)/C.sub.60 thin film cell with Ag as the metal cathode have been reported by Xue, et al., Appl. Phys. Lett., 2004, 84, 3013-3015. PV cells, enhanced by stacking two cells in series, and yielding efficiencies exceeding 5.5 percent have also been reported. Xue, et al., Appl. Phys. Lett. 2004, 85, 5757-5759. [0017] For additional background explanation and description of the state of the art for organic photosensitive devices, including their general construction, characteristics, materials, and features, U.S. Pat. No. 6,657,378 to Forrest et al., U.S. Pat. No. 6,580,027 to Forrest et al., and U.S. Pat. No. 6,352,777 to Bulovic et al. are incorporated herein by reference. [0018] Further improvements in the efficiency of organic photosensitive devices would clearly be advantageous. The present invention provides such organic photosensitive devices with improved efficiency. SUMMARY OF THE INVENTION [0019] The invention is directed to organic photosensitive optoelectronic devices, comprising an anode, a cathode, and a donor-acceptor heterojunction between the anode and the cathode. The heterojunction comprises a donor-like material and an acceptor-like material, where at least one of the donor-like material and the acceptor-like material comprises a subphthalocyanine, a subporphyrin, and/or a subporphyrazine compound; and/or the device optionally comprises at least one of a blocking layer or a charge transport layer, wherein the blocking layer and/or the charge transport layer comprises a subphthalocyanine, a subporphyrin, and/or a subporphyrazine compound. [0020] The invention is further directed to a method of preparing a heterojunction, where the heterojunction comprises a donor-like material and an acceptor-like material. The method comprises selecting a donor-like material having a LUMO and a HOMO, selecting a subphthalocyanine, a subporphyrin, or a subporphyrazine material, substituted with at least one electron withdrawing or electron donating substituent group, wherein the substituent group modulates the subphthalocyanine, subporphyrin, or subporphyrazine material LUMO and HOMO, such that the subphthalocyanine, subporphyrin, or subporphyrazine material is an acceptor-like material for the donor-like material, and forming a heterojunction from the donor-like and acceptor like materials; or selecting an acceptor-like material, selecting a subphthalocyanine, a subporphyrin, or a subporphyrazine material, substituted with at least one electron withdrawing or electron donating substituent group, wherein the substituent group modulates the subphthalocyanine, subporphyrin, or subporphyrazine material LUMO and HOMO, such that the subphthalocyanine, subporphyrin, or subporphyrazine material is a donor-like material for the acceptor-like material, and forming a heterojunction from the donor-like and acceptor like materials. 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