Transition Metal Complexes (e.g., Ru(ii) Polypyridine Complexes) (epo) Patents (Class 257/E51.044)
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Patent number: 8053974Abstract: In a general formula (1), each of R1 and R2 represents any one of hydrogen, an alkyl group, a halogen group, —CF3, an alkoxy group, and an aryl group. M represents an element that belongs to Group 9 or Group 10. Here, an alkyl group having 1 to 4 carbon atoms is preferable in the alkyl group. A fluoro group is particularly preferable in the halogen group. An alkoxy group having 1 to 4 carbon atoms is preferable in the alkoxy group. A phenyl group is particularly preferable in the aryl group. Iridium is particularly preferable among the elements that belong to Group 9, and platinum is particularly preferable among the elements that belong to Group 10. The general formula (1) is inserted.Type: GrantFiled: March 22, 2006Date of Patent: November 8, 2011Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Satoshi Seo, Hideko Inoue, Nobuharu Ohsawa
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Patent number: 8053090Abstract: Provided are a high-efficiency phosphorescent multinuclear copper complex and an organic electroluminescent device using the complex. The multinuclear copper complex can be used to form an organic layer of an organic electroluminescent device, and the organic electroluminescent device using the complex can emit light in the yellow to red wavelength region of 560 nm to 630 nm as a high-efficiency photoluminescent material, and provides a high brightness and a low turn-on voltage.Type: GrantFiled: May 18, 2007Date of Patent: November 8, 2011Assignee: Samsung Mobile Display Co., Ltd.Inventors: Das Rupasree Ragini, Hee-Kyung Kim, Yi-Yeol Lyu, Young-Hun Byun, O-Hyun Kwon, Jhun-Mo Son, Jung-Bae Song
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Patent number: 8048540Abstract: An organometallic complex with high emission efficiency and an organic light-emitting element having the organometallic complex are described. The organometallic complex has a structure represented by the following general formula (G1?).Type: GrantFiled: December 26, 2007Date of Patent: November 1, 2011Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Hideko Inoue, Satoshi Seo, Nobuharu Ohsawa
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Patent number: 8048538Abstract: A organic electroluminescent device comprising: a pair of electrodes; and at least one organic layer between the pair of electrodes, wherein the at least one organic layer contains a specific compound in which a transition metal and a carbene carbon are bonded to each other.Type: GrantFiled: April 25, 2006Date of Patent: November 1, 2011Assignee: FUJIFILM CorporationInventors: Takeshi Murakami, Kazunari Yagi, Seiji Ichijima, Tatsuya Igarashi, Tasuku Satou
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Patent number: 8048537Abstract: Provided is a cyclometalated transition metal complex represented by Formula 1: The cyclometalated transition metal complex contains a new ancillary ligand having a carboxylate acid or the like connected to a hetero ring, so that it can efficiently emit red light from a phosphorous material through intersystem crossing (ISC) to form triplet excitons and then metal to ligand charge transfer (MLCT). An organic light emitting device manufactured using the transition metal complex shows excellent luminous efficiency and external quantum efficiency.Type: GrantFiled: December 6, 2006Date of Patent: November 1, 2011Assignee: Samsung Mobile Display Co., Ltd.Inventors: Young-Hun Byun, Hee-Kyung Kim, Das Rupasree Ragini, O-Hyun Kwon, Yi-Yeol Lyu, Lyong-Sun Pu, Shinichiro Tamura
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Patent number: 8043724Abstract: The invention provides emissive materials and organic light emitting devices using the emissive materials in an emissive layer disposed between and electrically connected to an anode and a cathode. The emissive materials include compounds with the following structure: wherein at least one of R8 to R14 is phenyl or substituted phenyl, and/or at least two of R8 to R14 that are adjacent are part of a fluorenyl group. The emissive materials have enhanced electroluminescent efficiency and improved lifetime when incorporated into light emitting devices.Type: GrantFiled: February 11, 2008Date of Patent: October 25, 2011Assignee: The University of Southern CaliforniaInventors: Mark E. Thompson, Arnold Tamayo, Peter Djurovich
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Patent number: 8039124Abstract: Electro luminescent metal, e.g. Ir, complexes are disclosed. The metal complexes comprise at least one ligand L1 and at least one ligand L2, wherein ligand L1 is a 2-phenylpyridine ligand (I), comprising a phenyl ring (A) and a pyridine ring (B). The integers 2 to 9 denote positions in which substitutions can be made, and by the use of different substituents, e.g. 2,4-difluoro and 7-N(CH3)2, the emission wavelength of the complex may be tuned. The ligand L2 may e.g. be a compound of the following formula (II).Type: GrantFiled: June 26, 2006Date of Patent: October 18, 2011Assignee: Koninklijke Philips Electronics N.V.Inventors: Mohammad Khaja Nazeeruddin, Rene Theodorus Wegh, Steve Klink, Michael Graetzel, Cedric Nicolas Klein
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Patent number: 8039123Abstract: Provided are a high-efficiency, photoluminescent heteronuclear copper (I)-iridium (III) complex and an organic electroluminescent device using the complex. The photoluminescent heteronuclear copper (I)-iridium (III) complex can be used to form an organic layer of an organic electroluminescent device, can emit light of 590-630 nm as a high-efficiency, photoluminescent material, and provides a high brightness and a low turn-on voltage.Type: GrantFiled: March 27, 2007Date of Patent: October 18, 2011Assignee: Samsung Mobile Display Co., Ltd.Inventors: Das Rupasree Ragini, Hee-Kyung Kim, Byoung-Ki Choi, Yi-Yeol Lyu, Young-Hun Byun, O-Hyun Kwon, Che-Un Yang, Jung-Bae Song
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Patent number: 8022212Abstract: A light-emitting element having excellent light-emitting properties and with which it is possible to emit blue light at a high luminance for a long period of time, and an iridium complex for realizing the same. The light-emitting element has an external quantum efficiency of at least 5% and a light emission maximum wavelength ? max of no more than 500 nm. Further, there is provided a light-emitting element including a light-emitting layer or a plurality of organic compound layers having the light-emitting layer, with at least one of the compound layers including at least one kind of a compound having a partial structure represented by the general formula K-0. In the general formula K-0, R1 to R7 each independently represents a hydrogen atom or a substituent, provided that if R2 is a fluorine atom, R3 is not a hydrogen atom.Type: GrantFiled: November 1, 2007Date of Patent: September 20, 2011Assignee: FUJIFILM CorporationInventors: Tatsuya Igarashi, Toshihiro Ise, Yousuke Miyashita, Hidetoshi Fujimura, Hisashi Okada, Masayuki Mishima, Qiu Xuepeng
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Patent number: 8021763Abstract: The present invention relates to phosphorescent stacked OLEDs having an interlayer.Type: GrantFiled: November 23, 2005Date of Patent: September 20, 2011Assignee: The Trustees of Princeton UniversityInventors: Hiroshi Kanno, Stephen Forrest
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Patent number: 8012604Abstract: The present invention relates to heteroleptic electroluminescent metal complexes and to their preparation and use in electroluminescent devices, particularly to electroluminescent compounds having the general chemical formula:Type: GrantFiled: February 10, 2005Date of Patent: September 6, 2011Assignee: Merck Patent GmbHInventors: Poopathy Kathirgamanathan, Subramaniam Ganeshamurugan, Gnanamoly Paramaswara, Muthulingham Kumaraverl, Arumugam Partheepan, Selvadurai Selvaranjan, Juan Antipan-Lara, Richard Price, Sivagnanasundram Surendrakumar
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Patent number: 8008653Abstract: Disclosed herein are an organic memory device and a method for fabricating the memory device. The organic memory device may include a first electrode, a second electrode and an organic active layer between first and second electrodes, wherein the organic active layer is formed of a mixture of a conductive polymer and a metallocene compound. Because the organic memory device possesses decreased switching time, decreased operating voltage, decreased fabrication costs and increased reliability, the organic memory device may be used as a highly integrated large-capacity memory device.Type: GrantFiled: December 4, 2006Date of Patent: August 30, 2011Assignee: Samsung Electronics Co., Ltd.Inventors: Kwang Hee Lee, Tae Lim Choi, Won Jae Joo, Sang Kyun Lee
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Patent number: 8007925Abstract: The present invention provides an organic electroluminescence device using a novel phosphorescent metal complex compound and having high efficiency, high luminance, and high durability. The organic electroluminescence device includes a pair of electrodes including an anode and a cathode, and one or more organic layers each containing an organic compound, the one or more organic layers being interposed between the pair of electrodes, wherein at least one of the one or more organic layers contain a phosphorescent metal complex compound having at least one ligand structure represented by the following general formula (1): where at least one of X, Y and Z represents an aromatic oligomer having 13 or more carbon atoms and bonded directly or via a linking group.Type: GrantFiled: June 7, 2007Date of Patent: August 30, 2011Assignee: Canon Kabushiki KaishaInventors: Taiki Watanabe, Akira Tsuboyama, Satoru Shiobara, Koichi Suzuki, Kazunori Ueno
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Patent number: 8007926Abstract: An organic light emitting device is provided. The device has an anode, a cathode and an organic layer disposed between the anode and the cathode. The organic layer comprises a compound further comprising one or more carbene ligands coordinated to a metal center.Type: GrantFiled: June 2, 2008Date of Patent: August 30, 2011Assignee: The University of Southern CaliforniaInventors: Mark E. Thompson, Arnold Tamayo, Peter Djurovich, Tissa Sajoto
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Patent number: 8003226Abstract: A metal complex which has a metal complex structure showing light emission from triplet excited state, and has a monovalent group derived from carbazole, and a light-emitting device using said metal complex.Type: GrantFiled: March 24, 2003Date of Patent: August 23, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Kobayashi, Shuji Doi, Satoshi Mikami
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Patent number: 7998595Abstract: In an organic EL device, a hole injection electrode is formed on a glass substrate, and a hole injection layer, a hole transport layer and a luminescent layer are formed in turn on the hole injection electrode. An electron injection electrode is formed on the luminescent layer. The luminescent layer includes an organic iridium compound composed of a combination of a quinoline derivative and iridium. This organic iridium compound can emit red-orange light via a triplet excited state.Type: GrantFiled: February 12, 2002Date of Patent: August 16, 2011Assignee: Sanyo Electric Co., Ltd.Inventors: Yuji Hamada, Noriyuki Matsusue
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Patent number: 7985492Abstract: Novel ruthenium, rhodium, palladium, osmium, iridium or platinum complexes of dibenzothiophene ligands are electroluminescent compounds.Type: GrantFiled: August 4, 2005Date of Patent: July 26, 2011Assignee: Merck Patent GmbHInventors: Poopathy Kathirgamanathan, Subramaniam Ganeshamurugan
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Patent number: 7982391Abstract: An organic electroluminescent device comprising two electrodes and at least one organic compound layer disposed between the electrodes, wherein a luminescent layer is included in the organic compound layers, the luminescent layer includes a fluorescent compound, at least one of the organic compound layers comprises an amplifying agent, the fluorescent compound emits fluorescent light upon application of voltage, the amplifying agent is capable of amplifying a number of singlet excitons and of amplifying luminescence intensity, and an amount of the amplifying agent is such an amount that at least 51% of light components emitted by the device upon the application of voltage is fluorescent light, wherein the fluorescent compound is selected from the group consisting of a distyryl arylene derivative, an oligoarylene derivative, an nitrogen-containing aromatic heterocyclic compound, a sulfur-containing heterocyclic compound, a metal complex, an oxo-substituted heterocyclic compound, an organosilicon compound and aType: GrantFiled: December 23, 2004Date of Patent: July 19, 2011Assignee: Fujifilm CorporationInventors: Tatsuya Igarashi, Toshihiro Ise
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Patent number: 7981524Abstract: An organic electroluminescent device is provided and has at least one organic layer between a pair of electrodes. The organic compound contains a compound represented by the following formula (I): Z1 and Z2 each represents a nitrogen-containing aromatic 6-membered ring coordinating to platinum atom at the nitrogen atom, Q represents a nitrogen-containing aromatic 5-membered ring having one or two nitrogen atoms, L1 and L2 each represents a single bond or a divalent group, and n represents 0 or 1.Type: GrantFiled: March 16, 2006Date of Patent: July 19, 2011Assignee: Fujifilm CorporationInventors: Toshihiro Ise, Tatsuya Igarashi, Ikuo Kinoshita, Takeshi Murakami
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Patent number: 7977861Abstract: A composition is described comprising a mixture of at least two different dendrimers A and B which possess the same core and the same repeating unit or units in the dendrons. Either the generation of at least one of said dendrons in one of said dendrimers (A) is different from the generation of at least one of the dendrons in the other of said dendrimers (B), or the number of dendrons in one of said dendrimers, or both, is different from the number of dendrons in the other of said dendrimers, or both.Type: GrantFiled: August 28, 2003Date of Patent: July 12, 2011Assignees: Isis Innovation Limited, The University Court of the University of St. AndrewsInventors: Paul Leslie Burn, Ifor David William Samuel
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Patent number: 7976958Abstract: A novel metal complex compound for an organic EL device is provided which has at least one partial structure represented by the general formula (1): M1L1??(1) in which the partial structure M1L1 is represented by the general formula (2): wherein M1 represents a metal atom selected from Ir, Pt, Rh, and Pd; Y1 represents an alkylene group having 2 to 6 carbon atoms; and at least one of hydrogen atoms directly bonded to the carbon atoms forming the alkylene group Y1 is substituted with a fluorine atom.Type: GrantFiled: November 27, 2007Date of Patent: July 12, 2011Assignee: Canon Kabushiki KaishaInventors: Takao Takiguchi, Masashi Hashimoto, Jun Kamatani, Satoshi Igawa, Shinjiro Okada
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Patent number: 7973126Abstract: Polymers including at least one structural unit derived from a compound of formula I or including at least one pendant group of formula II may be used in optoelectronic devices wherein R1, R3, R4 and R6 are independently hydrogen, alkyl, alkoxy, oxaalkyl, alkylaryl, aryl, arylalkyl, heteroaryl, substituted alkyl; substituted alkoxy, substituted oxaalkyl, substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted heteroaryl; R1a is hydrogen or alkyl; R2 is alkylene, substituted alkylene, oxaalkylene, CO, or CO2; R2a is alkylene; R5 is independently at each occurrence hydrogen, alkyl, alkylaryl, aryl, arylalkyl, alkoxy, carboxy, substituted alkyl; substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted alkoxy, X is halo, triflate, —B(OR1a)2, or ?located at the 2, 5- or 2, 7-positions; and L is derived from phenylpyridine, tolylpyridine, benzothienylpyridine, phenylisoquinoline, dibenzoquinozaline, fluorenylpyridine, ketopyrrole, 2-(1-naphthyl)benzoType: GrantFiled: December 17, 2007Date of Patent: July 5, 2011Assignee: General Electric CompanyInventors: Joseph John Shiang, Kelly Scott Chichak, James Anthony Cella, Larry Neil Lewis, Kevin Henry Janora
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Patent number: 7964292Abstract: A metal complex is provided which is used for an organic EL device and an organic light-emitting device which outputs light with high luminance and high efficiency. The metal complex has a structure in which a nitrogen atom in a 6- to 8-membered non-aromatic cyclic group is bonded to a metal atom. The organic light-emitting device includes a pair of electrodes which are an anode and a cathode, and an organic compound layer interposed between the electrodes. The organic compound layer contains the metal complex represented by the following structural formula.Type: GrantFiled: March 22, 2007Date of Patent: June 21, 2011Assignee: Canon Kabushiki KaishaInventors: Masashi Hashimoto, Takao Takiguchi, Shinjiro Okada
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Patent number: 7960040Abstract: An organic electroluminescence device comprising at least an organic layer between a pair of electrodes, wherein the organic electroluminescence device further includes at least an interlocked compound. An organic electroluminescence device exhibiting a high light emission efficiency and excellent driving durability is provided.Type: GrantFiled: February 23, 2007Date of Patent: June 14, 2011Assignee: Fujifilm CorporationInventor: Hisashi Okada
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Patent number: 7951472Abstract: An organic light-emitting device comprising a light-emitting layer or a plurality of thin organic compound layers containing a light emitting layer interposed between a pair of electrodes, wherein at least one layer comprises at least one light emitting material containing a compound having a partial structure represented by following formula (21) or a tautomer thereof: wherein the compound having the partial structure represented by formula (21) has two or more different ligands.Type: GrantFiled: March 16, 2010Date of Patent: May 31, 2011Assignee: FUJIFILM CorporationInventors: Tatsuya Igarashi, Keizo Kimura, Kazumi Nii
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Patent number: 7951945Abstract: A compound represented by following formula (24): wherein R11 and R12 each represents a substituent; m1 represents an integer of from 0 to 4; m2 represents an integer of from 0 to 6; Z2 represents an atomic group which forms an aryl ring or a heteroaryl ring; Z3 represents an atomic group which forms a nitrogen-containing heteroaryl ring; and n1 represents an integer of from 1 to 3.Type: GrantFiled: March 15, 2010Date of Patent: May 31, 2011Assignee: FUJIFILM CorporationInventors: Tatsuya Igarashi, Keizo Kimura, Kazumi Nii
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Patent number: 7951471Abstract: It is an object of the present invention to provide a substance capable of emitting phosphorescence. In addition, it is an object of the present invention to provide a light-emitting element that is excellent in chromaticity. One aspect of the present invention is an organometallic complex having a structure represented by a general formula (1). In the general formula (1), R1 to R4 are each any one of hydrogen, a halogen element, an acyl group, an alkyl group, an alkoxyl group, an aryl group, a cyano group, and a heterocyclic group. In addition, R5 to R13 are each any one of hydrogen, an acyl group, an alkyl group, an alkoxyl group, an aryl group, a heterocyclic group, and an electron-withdrawing group. An organometallic complex having such a structure can emit phosphorescence with higher emission intensity.Type: GrantFiled: December 1, 2005Date of Patent: May 31, 2011Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Hideko Inoue, Satoko Shitagaki, Satoshi Seo
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Patent number: 7951947Abstract: A compound represented by following formula (23): wherein R11 and R12 each represents a substituent; R13, R14 and R15 each represents a hydrogen atom or a substituent; m1 represents an integer of from 0 to 4; and m2 represents an integer of from 0 to 6.Type: GrantFiled: March 16, 2010Date of Patent: May 31, 2011Assignee: FUJIFILM CorporationInventors: Tatsuya Igarashi, Keizo Kimura, Kazumi Nll
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Patent number: 7951946Abstract: A light-emitting material comprising a compound having a partial structure represented by following formula (21) or a tautomer thereof:Type: GrantFiled: March 16, 2010Date of Patent: May 31, 2011Assignee: FUJIFILM CorporationInventors: Tatsuya Igarashi, Keizo Kimura, Kazumi Nii
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Patent number: 7951944Abstract: An organic electroluminescent device (OELD) is provided. The OELD includes a substrate, an anode, a cathode, a hole transport layer, an electron transport layer and an emission layer. The anode and the cathode are disposed on the substrate. The hole transport layer is disposed between the anode and the cathode. The electron transport layer is disposed between the hole transport layer and the cathode. The emission layer is disposed between the hole transport layer and the electron transport layer. The emission layer includes a host and a dopant. The chemical structure of the dopant is shown as the formula [I]: “M” is a metal atom whose atomic weight is greater than 40. “S” is selected from a group consisting of alkyl, alkoxy, haloalkyl, halogen, hydrogen and any other substituents.Type: GrantFiled: March 2, 2009Date of Patent: May 31, 2011Assignee: Au Optronics Corp.Inventor: Cheng-Hung Lin
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Patent number: 7947383Abstract: An organic electroluminescent device having a pair of electrodes and at least one organic layer including a light-emitting layer interposed between the pair of electrodes, in which the organic layer contains at least one compound represented by formula (I): wherein Z1 and Z2 each independently represent a nitrogen-containing heterocycle coordinated with the platinum through a nitrogen atom; Q1 and Q2 each independently represent a group bonded with the platinum through a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorous atom; Q1 and Q2 each represent a structure different from each other; L1 and L2 each independently represent a single bond or a linking group; and n represents 0 or 1.Type: GrantFiled: September 20, 2005Date of Patent: May 24, 2011Assignee: Fujifilm CorporationInventors: Toshihiro Ise, Seiji Ichijima, Takeshi Murakami, Satoshi Sano
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Patent number: 7943925Abstract: A high efficient white emission light emitting element having peak intensity in each wavelength region of red, green, and blue is provided. Specifically, a white emission light emitting element having an emission spectrum that is independent of current density is provided. A first light emitting layer 312 exhibiting blue emission and a second light emitting layer 313 containing a phosphorescent material that generates simultaneously phosphorescent emission and excimer emission are combined. In order to derive excimer emission from the phosphorescent material, it is effective to disperse a phosphorescent material 323 having a high planarity structure such as platinum complex at a high concentration of at least 10 wt % to a host material 322. Further, the first light emitting layer 312 is provided to be in contact with the second light emitting layer 313 at the side of an anode. Ionization potential of the second light emitting layer 313 is preferably larger by 0.Type: GrantFiled: March 8, 2004Date of Patent: May 17, 2011Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventor: Hiroko Yamazaki
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Publication number: 20110108827Abstract: An organometallic complex represented by Formula 1 is provided. An organic light-emitting diode using the organometallic complex exhibits improved current and power efficiency and long lifetime.Type: ApplicationFiled: January 19, 2011Publication date: May 12, 2011Applicant: SFC CO., LTD.Inventors: Jong-Tae JE, Hyun-Jung KWON, Sang-Hae LEE
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Patent number: 7939821Abstract: It is an object of the present invention to provide a substance which can emit red phosphorescence which is closer to the chromaticity coordinates of red according to the NTSC standard. The present invention provides an organometallic complex represented by the general formula (1), wherein each of R1 to R3 represents any one of hydrogen, a halogen group, an acyl group, an alkyl group, an alkoxyl group, an aryl group, a cyano group, and a heterocyclic group, and at least one of R1 to R3 represents an electron-withdrawing group; and M represents a Group 9 element or a Group 10 element, and when M is the Group 9 element, n=2, whereas when M is the Group 10 element, n=1. Such an organometallic complex can emit red phosphorescence with good spectral luminous efficiency which is closer to the chromaticity coordinates of red according to the NTSC standard.Type: GrantFiled: January 21, 2010Date of Patent: May 10, 2011Assignee: Semiconductor Energy laboratory Co., Ltd.Inventors: Hideko Inoue, Satoshi Seo
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Patent number: 7927717Abstract: Electroluminescent devices have an electroluminescent layer incorporating iridium complexes with 2-benzo[b]thiophenyl and benzimidazole ligands such as bis[thiophen-2-yl-pyridine-C2,N?]-2-(2-pyridyl)-benzimidazole iridium.Type: GrantFiled: June 30, 2005Date of Patent: April 19, 2011Assignee: Merck Patent GmbHInventors: Poopathy Kathirgamanathan, Subramaniam Ganeshamurugan, Muttulingam Kumaraverl, Arumugam Partheepan, Gnanamoly Paramaswara, Juan Antipan-Lara
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Patent number: 7902374Abstract: Organic light emitting materials and devices comprising phosphorescent metal complexes comprising ligands comprising aryl or heteroaryl groups substituted at both ortho positions are described. An organic light emitting device, comprising: an anode; a hole transport layer; an organic emissive layer comprising an emissive layer host and an emissive dopant; an electron impeding layer; an electron transport layer; and a cathode disposed, in that order, over a substrate.Type: GrantFiled: November 3, 2006Date of Patent: March 8, 2011Assignee: Universal Display CorporationInventors: Chun Lin, Peter B. Mackenzie, Robert W. Walters, Jui-Yi Tsai, Cory S. Brown, Jun Deng
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Patent number: 7893430Abstract: An OLED device having an emission layer formed of an ambipolar phosphine oxide host material and a dopant, a hole transport layer in electrical communication with an anode, an electron transport layer in communication with a cathode, wherein the HOMO energy of the hole transport layer is substantially the same as the HOMO energy of the ambipolar host in the emission layer, and the LUMO energy of the electron transport layer is substantially the same as the LUMO energy of the ambipolar host in the emission layer.Type: GrantFiled: February 26, 2009Date of Patent: February 22, 2011Assignee: Battelle Memorial InstituteInventors: Linda Susan Sapochak, Paul Edward Burrows, Asanga Bimalchandra
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Patent number: 7883787Abstract: Organic light emitting devices are described wherein the emissive layer comprises a host material containing an emissive molecule, which molecule is adapted to luminesce when a voltage is applied across the heterostructure, and the emissive molecule is selected from the group of phosphorescent organometallic complexes, including cyclometallated platinum, iridium and osmium complexes. The organic light emitting devices optionally contain an exciton blocking layer. Furthermore, improved electroluminescent efficiency in organic light emitting devices is obtained with an emitter layer comprising organometallic complexes of transition metals of formula L2MX, wherein L and X are distinct bidentate ligands. Compounds of this formula can be synthesized more facilely than in previous approaches and synthetic options allow insertion of fluorescent molecules into a phosphorescent complex, ligands to fine tune the color of emission, and ligands to trap carriers.Type: GrantFiled: May 1, 2009Date of Patent: February 8, 2011Assignees: The Trustees of Princeton University, The University of Southern CaliforniaInventors: Mark E. Thompson, Peter Djurovich, Sergey Lamansky, Drew Murphy, Raymond Kwong, Feras Abdel-Razzaq, Stephen R. Forrest, Marc A. Baldo, Paul E. Burrows
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Patent number: 7883785Abstract: The present invention describes novel organometallic compounds which are phosphorescent emitters. Such compounds can be used as active components (=functional materials) in a variety of different applications which can in the widest sense be considered part of the electronics industry. The compounds of the invention are described by the formulae (I), (Ia), (II) and (IIa).Type: GrantFiled: August 14, 2003Date of Patent: February 8, 2011Assignee: Merck Patent GmbHInventors: Philipp Stössel, Ingrid Bach, Hubert Spreitzer
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Patent number: 7875366Abstract: The present invention provides a luminescent device using a luminescent material which has high luminescence efficiency and high stability, and is available at a low cost. The luminescent device is characterized in that as a luminescent material is used a binuclear copper coordination compound having a partial structure represented by the general formula (1): Cu-A-Cu, wherein Cu is a copper ion and A is a bidentate ligand.Type: GrantFiled: November 16, 2004Date of Patent: January 25, 2011Assignee: Canon Kabushiki KaishaInventors: Akira Tsuboyama, Jun Kamatani, Manabu Furugori, Shinjiro Okada, Takao Takiguchi
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Patent number: 7868321Abstract: Provided are an organic light emitting device (OLED) and a flat display including the OLED. The OLED includes an organic layer which includes a pixel electrode, an opposite electrode, and at least an emission layer between the pixel electrode and the opposite electrode, wherein the emission layer includes a long wavelength-blue emission layer emitting blue light having a long wavelength and a short wavelength-blue emission layer emitting blue light having a short wavelength. The long wavelength-blue emission layer is positioned in a location to enhance emission of blue light from the emission layer. The OLED can emit blue light with high efficiency and high brightness.Type: GrantFiled: January 18, 2007Date of Patent: January 11, 2011Assignee: Samsung Mobile Display Co., Ltd.Inventors: Chang-Ho Lee, Seung-Gak Yang, Hee-Yeon Kim, Jung-Han Shin, Hee-Joo Ko
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Patent number: 7851072Abstract: An organic light emitting device is provided. The device has an anode, a cathode, and an emissive layer disposed between the anode and the cathode. The emissive layer may include a molecule of Formula I wherein an alkyl substituent at position R?5 results in high efficiency and operational stability in the organic light emitting device. Additionally or alternatively, the emissive layer may include a metal-ligand complex in which the ligand is an aryl or alkyl substituted phenylpyridine ligand.Type: GrantFiled: May 19, 2006Date of Patent: December 14, 2010Assignee: Universal Display CorporationInventors: Raymond Kwong, David Knowles, Bin Ma, William Ceyrolles
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Patent number: 7824778Abstract: Devices are provided having an anode, a cathode, and an emissive layer disposed between and electrically connected to the anode and the cathode. The emissive layer includes an emissive material having more than one metal center. In one embodiment, first and second metal centers are independently selected from the group consisting of d7, d8, and d9 metals. A bridging ligand is coordinated to the first metal center and to the second metal center. In one embodiment, the first and second metal centers each have coordination numbers of at least 3, and more preferably each have coordination numbers of 4. In one embodiment, photoactive ligands are coordinated to the first and second metal centers. In one embodiment, there are no photoactive ligands. In one embodiment, a charge neutral bi-nuclear emissive material is provided. In one embodiment the first and metal centers have a co-facial configuration, and preferably a square planar co-facial configuration.Type: GrantFiled: May 15, 2006Date of Patent: November 2, 2010Assignee: The University of Southern CaliforniaInventors: Mark E. Thompson, Bert Alleyne, Peter Djurovich
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Patent number: 7816016Abstract: Provided are complexes of the formula: where R1 is H, R4, OR4, N(R4)2 or CHAr2; R2 is H, CnF2n+1, CnF2n+1 SO2, COOR4, or CN; R3 is H, CnF2n+1, CnF2n+1SO2, COOR4, or CN; R4 is the same or different at each occurrence and is H, alkyl, or aryl, or adjacent R4 groups can join together to form a 5- or 6-membered ring, or adjacent R4 groups can join together to form a 5- or 6-membered ring; or adjacent R4 groups can join together to form a multicyclic moiety; each Ar is independently an aryl group; L? is a polydentate ligand that is not a phenylpyridine, phenylpyrimidine, or phenylquinoline; L? is a monodentate ligand, and is not a phenylpyridine, and phenylpyrimidine, or phenylquinoline; m is 1, 2 or 3; n is an integer from 1 through 20; y is 0, 1 or 2; and z is 0 or an integer from 1 through 4; with the proviso that the compound is charge neutral and the iridium is hexacoordinate.Type: GrantFiled: December 22, 2005Date of Patent: October 19, 2010Assignee: E. I. du Pont de Nemours and CompanyInventors: Norman Herron, Mark A. Guidry, Viasceslav Petrov, Nora Sabina Radu
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Patent number: 7816018Abstract: An organic electroluminescent material having the formula and an organic electroluminescent material used for electroluminescent devices is characterized by emission with a high luminance, high illuminant efficiency, low drive voltage, favorable color purity and high thermal steadiness. The hydrogen atom, halogen atom, cyanide group, alkyl group, alkylidene group, cycloalkane group, alkoxy group, amino group, aromatic hydroxy group, alkylaryl group as a substitutive group are used. Not only may it increase the material's glass transition temperature and inhibit the phenomenon of molecular split but also cause this organic electroluminescent device to show a high level of steadiness.Type: GrantFiled: November 21, 2006Date of Patent: October 19, 2010Assignee: Grace Semiconductor Manufacturing CorporationInventor: Hsiang-Lun Hsu
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Patent number: 7811677Abstract: It is an object of the present invention to obtain an organometallic complex that is capable of converting an excited triplet state into luminescence, a light-emitting element that can be driven for a long time, is high in luminous efficiency, and has a favorable long lifetime, and a light-emitting device using the light-emitting element. The present invention provides a light-emitting element that has a pair of electrodes (an anode and a cathode) and a light-emitting layer between a pair of electrodes, where the light-emitting layer includes an organometallic complex represented by the following general formula (5) and one of a compound that has a larger energy gap than the organometallic complex and a compound that has a larger ionization potential and a smaller electron affinity than the organometallic complex, and provides a light-emitting device using the light-emitting device.Type: GrantFiled: May 17, 2005Date of Patent: October 12, 2010Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Nobuharu Ohsawa, Hiroko Abe, Hideko Inoue, Satoko Shitagaki, Satoshi Seo
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Patent number: 7807275Abstract: An organic light emitting diode (OLED) architecture in which efficient operation is achieved without requiring a blocking layer by locating the recombination zone close to the hole transport side of the emissive layer. Aryl-based hosts and Ir-based dopants with suitable concentrations result in an efficient phosphorescent OLED structure. Previously, blocking layer utilization in phosphorescent OLED architectures was considered essential to avoid exciton and hole leakage from the emissive layer, and thus keep the recombination zone inside the emissive layer to provide high device efficiency and a pure emission spectrum.Type: GrantFiled: April 21, 2005Date of Patent: October 5, 2010Assignee: Universal Display CorporationInventors: Vadim Adamovich, Michael Stuart Weaver, Raymond Kwong
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Patent number: 7803468Abstract: An organic electroluminescent element including a pair of electrodes and one or more organic compound layers including at least one light-emitting layer disposed between the pair of electrodes, wherein the at least one light-emitting layer contains at least one luminescent dopant and a plurality of host compounds. The ionization potential of the dopant is Ip(D), the minimum value out of the ionization potentials of the plurality of host compounds is Ip(H)min, and ?Ip is defined by ?Ip=Ip(D)?Ip(H)min and satisfies a relationship of ?Ip>0 eV. The electron affinity of the dopant is Ea(D), the maximum value out of the electron affinities of the plurality of host compounds is Ea(H)max, and ?Ea is defined by ?Ea=EA(H)max?Ea(D) and satisfies a relationship of ?Ea>0 eV.Type: GrantFiled: September 28, 2005Date of Patent: September 28, 2010Assignee: Fujifilm CorporationInventors: Fumito Nariyuki, Kazuki Yamazaki
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Patent number: 7795799Abstract: A light-emitting device which can effectively be utilized as a surface light source for a full-color display, a back light or an illumination light source, or as a light source array in a printer, which shows an excellent light-emitting efficiency and light-emitting luminance, and which is particularly excellent as a white light source showing an excellent light-emitting efficiency and light-emitting luminance. The light-emitting device comprises a substrate having provided thereon at least an anode, an organic compound layer including a light-emitting layer, and a cathode, in which the light-emitting layer contains two or more different kinds of light-emitting materials, with at least one of the light-emitting materials being an orthometallated complex.Type: GrantFiled: May 1, 2001Date of Patent: September 14, 2010Assignee: Fujifilm CorporationInventor: Masayuki Mishima
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Patent number: RE42561Abstract: An organic light emitting device structure having an organic light emitting device (OLED) over a substrate, where the OLED has, for example, an anode, a hole transporting layer (HTL), a first electron transporting layer (ETL) that is doped with a phosphorescent material, a second electron transporting layer (ETL), and a cathode. The OLEDs of the present invention are directed, in particular, to devices that include an emissive layer comprised of an electron transporting host material having a triplet excited state energy level that is higher than the emissive triplet excited state energy level of the phosphorescent dopant material.Type: GrantFiled: April 16, 2007Date of Patent: July 19, 2011Assignees: The University of Southern California, The Trustees of Princeton UniversityInventors: Chihaya Adachi, Marc A. Baldo, Stephen R. Forrest