The Five-membered Hetero Ring Shares Ring Carbons With Two Benzene Rings (i.e., Carbazoles) Patents (Class 548/440)
  • Patent number: 11678567
    Abstract: This invention discloses a novel two dimensional material having propellane core for organic light emitting diodes. These compounds can be used as hosts, charging transporting materials, or blocking materials for PHOLEDs. The devices comprising these compounds have better performance due to the honeycomb pi-extended structure in the propellane molecules.
    Type: Grant
    Filed: February 26, 2020
    Date of Patent: June 13, 2023
    Assignee: Universal Display Corporation
    Inventors: Bin Ma, Chun Lin
  • Patent number: 11655205
    Abstract: A compound for an organic optoelectronic device, an organic optoelectronic device, and a display device including the same, the compound being represented by Chemical Formula 1:
    Type: Grant
    Filed: September 1, 2020
    Date of Patent: May 23, 2023
    Assignee: SAMSUNG SDI CO., LTD.
    Inventors: Dong Wan Ryu, Jinhyun Lui, Hyunji Yoo, Youngkyoung Jo, Seungchul Lyu, Min Seok Seo, Ho Kuk Jung, Sung-Hyun Jung
  • Patent number: 11653563
    Abstract: An organic light-emitting device including a first compound represented by Formula 1 and a second compound represented by one of Formulae 2A and 2B.
    Type: Grant
    Filed: December 9, 2016
    Date of Patent: May 16, 2023
    Assignee: SAMSUNG DISPLAY CO., LTD.
    Inventors: Myeong-Suk Kim, Hee-Yeon Kim, Hwan-Hee Cho, Seung-Gak Yang
  • Patent number: 11638390
    Abstract: The present disclosure relates in part to compounds capable of emitting delayed fluorescence and uses of these compounds in organic light-emitting diodes.
    Type: Grant
    Filed: June 25, 2018
    Date of Patent: April 25, 2023
    Assignee: KYULUX, INC.
    Inventors: Jorge Aguilera-Iparraguirre, Rafael Gomez-Bombarelli, Timothy D Hirzel, Shuo-Hsien Cheng, Yu Seok Yang, Naoto Notsuka, Yoshitake Suzuki, Ayataka Endo, Keiro Nasu, Tsang Ping Kuen
  • Patent number: 11611044
    Abstract: An organic light-emitting device including a first compound represented by Formula 1 and a second compound represented by one of Formulae 2A and 2B.
    Type: Grant
    Filed: December 9, 2016
    Date of Patent: March 21, 2023
    Assignee: SAMSUNG DISPLAY CO., LTD.
    Inventors: Myeong-Suk Kim, Hee-Yeon Kim, Hwan-Hee Cho, Seung-Gak Yang
  • Patent number: 11608327
    Abstract: The present invention describes amines with dibenzofuran, dibenzothiophene and fluorene groups, especially for use as triplet matrix materials in organic electroluminescent devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.
    Type: Grant
    Filed: February 6, 2017
    Date of Patent: March 21, 2023
    Assignee: MERCK PATENT GMBH
    Inventors: Amir Hossain Parham, Thomas Eberle, Anja Jatsch, Tobias Grossmann, Jonas Valentin Kroeber, Elvira Montenegro, Caroline Wern
  • Patent number: 11600782
    Abstract: Novel host compounds consisting of carbazole and nitrile groups are disclosed. These compounds are useful in phosphorescent OLEDs.
    Type: Grant
    Filed: July 15, 2019
    Date of Patent: March 7, 2023
    Assignee: Universal Display Corporation
    Inventors: Lichang Zeng, Chuanjun Xia
  • Patent number: 11588113
    Abstract: Disclosed is an organic light emitting diode (OLED) includes a first emitting material layer, which includes a first compound and a second compound, and a second emitting material layer, which includes a third compound and a fourth compound, wherein a HOMO energy level of the first compound is higher than a HOMO energy level of the second compound and a HOMO energy level of the third compound is lower than a HOMO energy level of the fourth compound, and an organic light emitting device having the OLED. The OLED and the organic light emitting device disclosed have enhanced luminous efficiency, color purity and luminous life span as well as low driving voltage by applying the emitting material layer.
    Type: Grant
    Filed: July 22, 2019
    Date of Patent: February 21, 2023
    Assignees: LG DISPLAY CO., LTD., LG CHEM, LTD.
    Inventors: Tae-Ryang Hong, Hyong-Jong Choi, Jun-Yun Kim, Wan-Pyo Hong, Jin-Joo Kim, Hong-Sik Yoon
  • Patent number: 11578063
    Abstract: The present invention relates to compounds of formula (1) which are suitable for use in electronic devices:
    Type: Grant
    Filed: October 15, 2018
    Date of Patent: February 14, 2023
    Assignee: MERCK PATENT GMBH
    Inventors: Rouven Linge, Sebastian Meyer, Lara-Isabel Rodriguez
  • Patent number: 11572592
    Abstract: The invention provides monoferrocenyl compounds of general formula I. The invention also provides substrates labelled with the compounds, functionalised derivatives of the compounds and methods of using the compounds, functionalised derivatives and labelled substrates in electrochemical assays.
    Type: Grant
    Filed: April 5, 2021
    Date of Patent: February 7, 2023
    Assignee: Binx Health Limited
    Inventors: Barrie J. Marsh, Christopher G. Frost, Jonathan Sharp
  • Patent number: 11569454
    Abstract: Provided are an organic-light-emitting device and a display apparatus including the same. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including at least one light-emitting unit, wherein the at least one light-emitting unit includes: an emission layer; and a hole transport region between the first electrode and the emission layer and including a first hole transport (HT) layer, the emission layer includes a host, the first HT layer includes a first compound, a minimum bond dissociation energy (BDE1HT) of the first compound is larger than a triplet energy (T1,host) of the host, and a minimum bond dissociation energy (BDEhost) of the host is larger than the triplet energy (T1,host) of the host.
    Type: Grant
    Filed: March 9, 2020
    Date of Patent: January 31, 2023
    Assignee: Samsung Display Co., Ltd.
    Inventors: Jaeyong Lee, Taekyung Kim, Minkyung Kim, Seulong Kim, Pilgu Kang, Jiyoung Kwon, Soonchul Chang, Jaehoon Hwang
  • Patent number: 11538996
    Abstract: The present invention relates to a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.
    Type: Grant
    Filed: September 6, 2019
    Date of Patent: December 27, 2022
    Assignee: MERCK PATENT GMBH
    Inventors: Frank Voges, Teresa Mujica-Fernaud, Elvira Montenegro
  • Patent number: 11495745
    Abstract: Provided is a compound of Chemical Formula 1: where R1 and R2 are each independently hydrogen, a substituted or unsubstituted C1-60 alkyl, a substituted or unsubstituted C1-60 alkoxy, a substituted or unsubstituted C1-60 haloalkyl, a substituted or unsubstituted C1-60 haloalkoxy, halogen, cyano, tri(C1-60 alkyl)silyl, a substituted or unsubstituted C6-60 aryl, or a substituted or unsubstituted C2-60 heteroaryl containing at least one of O, N, Si and S, R3 and R4 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-60 alkyl, a substituted or unsubstituted C1-60 alkoxy, a substituted or unsubstituted C1-60 haloalkyl, a substituted or unsubstituted C1-60 haloalkoxy, halogen, cyano, tri(C1-60 alkyl)silyl, or a substituted or unsubstituted C2-60 heteroaryl containing at least one of O, N, Si and S, and Ar is C6-60 aryl, or C2-60 heteroaryl containing at least one of O, N, Si and S, wherein the C6-60 aryl, or C2-60 heteroaryl is substituted with 1 to 5 substituents each selected from th
    Type: Grant
    Filed: October 17, 2018
    Date of Patent: November 8, 2022
    Assignee: LG CHEM, LTD.
    Inventors: Jun Yun, Joo Yong Yoon, Yeon Hwan Kim, Wanpyo Hong
  • Patent number: 11484871
    Abstract: Catalyst systems suitable for tetramerizing ethylene to form 1-octene may include a catalyst comprising a chromium compound coordinated with a ligand and a co-catalyst comprising an organoaluminum compound. The ligand may include have a chemical structure according to formula (I), wherein at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 have the structure according to formula (II) wherein RA, RB, RC, and RD and the remainder of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are independently chosen from a hydrogen or a (C1-C50) hydrocarbyl group.
    Type: Grant
    Filed: November 22, 2021
    Date of Patent: November 1, 2022
    Assignees: Saudi Arabian Oil Company, King Fahd University of Petroleum and Minerals
    Inventors: Ea Jaseer, Samir Barman, Nestor Garcia Villalta, Motaz Khawaji, Wei Xu, Fahad Almalki
  • Patent number: 11393984
    Abstract: An organic molecule is disclosed comprising: a first chemical moiety with a structure of formula I, and two second chemical moieties, independently from another with a structure of formula II, wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond.
    Type: Grant
    Filed: April 13, 2018
    Date of Patent: July 19, 2022
    Assignee: CYNORA GmbH
    Inventor: Alhama Arjona Esteban
  • Patent number: 11261374
    Abstract: The present invention addresses the issue of providing: a novel squarylium compound that has high light-emission efficiency, in particular little reduction in light-emission efficiency in a solid membrane, and is capable of emitting a near-infrared light having excellent light resistance; and a light-emitting composition and a light-emitting film that contain said squarylium compound. This squarylium compound is characterized by having a structure indicated by general formula (1).
    Type: Grant
    Filed: September 2, 2019
    Date of Patent: March 1, 2022
    Assignee: KONICA MINOLTA, INC.
    Inventor: Ryutaro Sugawara
  • Patent number: 11239439
    Abstract: To provide a light-emitting material of a light emitting layer, particularly a dopant material or a host material of a light emitting layer emitting delayed fluorescence, or a material suitable for a hole blocking layer, as a material for an organic electroluminescent device having a high efficiency, and also to provide an organic photoluminescent device or an organic electroluminescent device having a high efficiency and a high luminance, particularly an organic EL device suppressed in the roll-off phenomenon, by using the material. A material for an organic electroluminescent device, containing a benzonitrile derivative of the following general formula (1), and an organic electroluminescent device containing a pair of electrodes and one layer or plural layers including at least a light emitting layer intervening between the electrodes, the organic electroluminescent device using the material.
    Type: Grant
    Filed: March 14, 2016
    Date of Patent: February 1, 2022
    Assignees: Hodogaya Chemical Co., Ltd., Hirata Corporation, Kyulux, Inc.
    Inventors: Chihaya Adachi, Jun-Ichi Nishide, Yasuhide Hiraga, Takehiro Takahashi
  • Patent number: 11217754
    Abstract: According to the present invention, there is provided an organic electroluminescent device which has an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode arranged in order of description. The device is characterized in that: the hole transport layer includes a specific arylamine compound, and that the luminous layer includes a specific indenoindole derivative or a specific carbazole derivative. The organic EL device of the present invention has improved efficiency of hole transport from the hole transport layer to the luminous layer and also improved efficiency of electron transport from the electron transport layer to the luminous layer, in comparison to conventional organic EL devices.
    Type: Grant
    Filed: July 27, 2015
    Date of Patent: January 4, 2022
    Assignees: HODOGAYA CHEMICAL CO., LTD., SFC CO., LTD.
    Inventors: Shuichi Hayashi, Naoaki Kabasawa, Shunji Mochiduki, Se-Jin Lee, Oun-gyu Lee, Bong-Ki Shin
  • Patent number: 11043638
    Abstract: An organic electroluminescence device includes an anode, an emitting layer and a cathode, in which the emitting layer includes a first compound and a second compound. The first compound is a delayed-fluorescent compound. The second compound is represented by a formula (2) below, in which X is a nitrogen atom or a carbon atom bonded to Y; R21 to R26 are each independently a hydrogen atom or a substituent; Z21 and Z22 are each independently selected from the group consisting of a halogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy group.
    Type: Grant
    Filed: October 6, 2015
    Date of Patent: June 22, 2021
    Assignee: IDEMITSU KOSAN CO., LTD.
    Inventors: Toshinari Ogiwara, Kei Yoshida, Yuichiro Kawamura
  • Patent number: 10833282
    Abstract: An object is to provide a light-emitting element with high emission efficiency which includes a novel carbazole derivative that has a wide energy gap and can be used for a transport layer or a host material in a light-emitting element. A carbazole derivative in which the 4-position of dibenzothiophene or dibenzofuran is bonded to the 2- or 3-position of carbazole has been able to be provided by use of the carbazole derivative. Further, a light-emitting element having high emission efficiency has been able to be provided by use of the carbazole derivative.
    Type: Grant
    Filed: June 15, 2017
    Date of Patent: November 10, 2020
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Satoshi Seo, Harue Osaka, Sachiko Kawakami, Nobuharu Ohsawa, Tsuneori Suzuki, Hiromi Nowatari, Hiroki Suzuki, Kyoko Takeda
  • Patent number: 10622692
    Abstract: In one aspect, solar energy systems are described herein. In some embodiments, such a comprises an electrochemical cell comprising a photoelectrode, a counter electrode, and an ion transport membrane disposed between the photoelectrode and counter electrode. The cell further comprises a first electrolyte solution disposed in fluid communication with the photoelectrode and the membrane, and a second electrolyte solution disposed in fluid communication with the membrane and the counter electrode. The first and/or second electrolyte solution comprises a solvated redox pair. Additionally, the cell also comprises a storage electrode, a first external electrical connection between the photoelectrode and the counter electrode, and a second external electrical connection between the counter electrode and the storage electrode. Components of the system define a liquid junction photovoltaic cell under light conditions and a galvanic cell under dark conditions.
    Type: Grant
    Filed: May 18, 2016
    Date of Patent: April 14, 2020
    Assignee: Board of Regents, The University of Texas System
    Inventors: Fuqiang Liu, Dong Liu, Zi Wei, Yi Shen, Krishnan Rajeshwar
  • Patent number: 10454041
    Abstract: The present invention relates to a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.
    Type: Grant
    Filed: January 24, 2017
    Date of Patent: October 22, 2019
    Assignee: Merck Patent GmbH
    Inventors: Teresa Mujica-Fernaud, Elvira Montenegro
  • Patent number: 10374169
    Abstract: The present invention relates to an organic hole transport material having a compound of the structure shown in formula (I), wherein R1-R2 independently represent hydrogen, C1-C8 substituted or substituted alkyl, C2-C8 substituted or unsubstituted alkenyl, C2-C8 substituted or unsubstituted alkynyl, or C6-C10 substituted or substituted aryl, the substituents being C1-C4 alkyl or halogen. Device experiments show that the organic hole transport material of the present invention has high glass-transition temperature and high thermal stability; a hole-only organic semiconductor diode device and an organic electroluminescent device manufactured by the organic hole transport material have good hole transport performance, high and stable current efficiency, and a long device life.
    Type: Grant
    Filed: November 30, 2016
    Date of Patent: August 6, 2019
    Assignee: GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO. LTD
    Inventors: Kam-Hung Low, Chin-Hsin Chen, Zhe Li, Lei Dai, Lifei Cai
  • Patent number: 10326078
    Abstract: It is an object of the present invention to provide a light emitting element, which is resistant to repetition of an oxidation reaction. It is another object of the invention to provide a light emitting element, which is resistant to repetition of a reduction reaction. An anthracene derivative is represented by a general formula (1). In the general formula (1), R1 represents hydrogen or an alkyl group having 1 to 4 carbon atoms, R2 represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms, R3 represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 12 carbon atoms, Ph1 represents a phenyl group, and X1 represents an arylene group having 6 to 15 carbon atoms.
    Type: Grant
    Filed: October 17, 2016
    Date of Patent: June 18, 2019
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Harue Nakashima, Sachiko Kawakami, Kumi Kojima, Ryoji Nomura, Nobuharu Ohsawa
  • Patent number: 10281374
    Abstract: Disclosed are methods for treating a biological sample for an analyte-staining assay. These methods are conducted with the use of a single aqueous multi-functional composition for the purposes of performing the steps of deparaffinization, rehydration, antigen retrieval and endogenous enzyme blocking simultaneously optionally at an elevated temperature. These methods are alternatively conducted with use of a single aqueous multi-functional composition that contains a thermostable protease for the purpose of deparaffinization, rehydration, antigen retrieval and endogenous enzyme blocking at an elevated temperature.
    Type: Grant
    Filed: September 4, 2016
    Date of Patent: May 7, 2019
    Assignees: Diagnostic BioSystems
    Inventors: Marc Key, Bipin Gupta
  • Patent number: 10276804
    Abstract: The present invention relates to a compound for an organic optoelectronic element represented by Chemical Formula 1, an element comprising the same, and a display device comprising the organic optoelectronic element (details of Chemical Formula 1 are as described in the specification).
    Type: Grant
    Filed: August 6, 2015
    Date of Patent: April 30, 2019
    Assignee: Samsung SDI Co., Ltd.
    Inventors: Seung-Jae Lee, Dong-Min Kang, Eun-Sun Yu, Sang-Shin Lee, Sung-Hyun Jung, Ho-Kuk Jung, Su-Jin Han
  • Patent number: 10071993
    Abstract: An object is to provide a novel carbazole derivative that has an excellent carrier-transport property and can be suitably used for a transport layer or as a host material of a light-emitting element. Another object is to provide an organic semiconductor material and a light-emitting element material each using the carbazole derivative. As the carbazole derivative that can achieve the above objects, a carbazole derivative in which a carbazolyl group whose either 2- or 3-position of carbazole is substituted by the 4-position of a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to aromatic hydrocarbon that has 14 to 70 carbon atoms and includes a condensed tricyclic ring, a condensed tetracyclic ring, a condensed pentacyclic ring, a condensed hexacyclic ring, or a condensed heptacyclic ring has been able to be synthesized.
    Type: Grant
    Filed: September 13, 2016
    Date of Patent: September 11, 2018
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Hiroki Suzuki, Kyoko Takeda, Sachiko Kawakami, Tsunenori Suzuki, Satoshi Seo, Nobuharu Ohsawa
  • Patent number: 10050212
    Abstract: Disclosed is an organic optoelectric device, including an anode and a cathode facing each other, an emission layer interposed between the anode and the cathode, a hole transport layer interposed between the anode and the emission layer, and a hole transport auxiliary layer interposed between the hole transport layer and the emission layer. The emission layer includes at least one first compound represented by Chemical Formula 1: The emission layer further includes at least one second compound represented by Chemical Formula 2: The hole transport auxiliary layer includes a third compound represented by Chemical Formula 2, the third compound being the same as or different from the second compound.
    Type: Grant
    Filed: June 12, 2014
    Date of Patent: August 14, 2018
    Assignee: Cheil Industries, Inc.
    Inventors: Pyeong-Seok Cho, Gi-Wook Kang, Eui-Su Kang, Youn-Hwan Kim, Hun Kim, Yong-Tak Yang, Jae-Jin Oh, Eun-Sun Yu, Nam-Heon Lee, Sang-Shin Lee, Han-Ill Lee
  • Patent number: 9920167
    Abstract: A polymer having a repeating unit represented by Formula 1, wherein R1 through R14, X1, and Ar1 are the same as defined in the detailed description, and an organic light-emitting diode including the polymer are described.
    Type: Grant
    Filed: November 7, 2012
    Date of Patent: March 20, 2018
    Assignee: SAMSUNG ELECTRONICS CO., LTD.
    Inventors: Hye-yeon Yang, Ho-suk Kang, Jhun-mo Son, Yong-sik Jung, Mi-jeong Kim, Tae-gon Kim, Won-jae Joo, Hyeon-ho Choi, Seok-hwan Hong
  • Patent number: 9793485
    Abstract: The invention provides compositions comprising crosslinkable BCB-functionalized materials for use in OLEDs applications. The inventive compositions can be used to form hole-transporting materials for use in electroluminescent devices. In particular, the invention provides a composition comprising at least one compound selected from Structure A, as described herein.
    Type: Grant
    Filed: August 19, 2015
    Date of Patent: October 17, 2017
    Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLC
    Inventors: Minrong Zhu, Jichang Feng, Shaoguang Feng, Chun Liu, Nolan T. McDougal, David D. Devore, Peter Trefonas, III, Liam P. Spencer
  • Patent number: 9735372
    Abstract: An object is to provide a light-emitting element with high emission efficiency which includes a novel carbazole derivative that has a wide energy gap and can be used for a transport layer or a host material in a light-emitting element. A carbazole derivative in which the 4-position of dibenzothiophene or dibenzofuran is bonded to the 2- or 3-position of carbazole has been able to be provided by use of the carbazole derivative. Further, a light-emitting element having high emission efficiency has been able to be provided by use of the carbazole derivative.
    Type: Grant
    Filed: June 22, 2015
    Date of Patent: August 15, 2017
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Satoshi Seo, Harue Osaka, Sachiko Kawakami, Nobuharu Ohsawa, Tsunenori Suzuki, Hiromi Nowatari, Hiroki Suzuki, Kyoko Takeda
  • Patent number: 9650565
    Abstract: A carbazole compound represented by the following formula: wherein, when m=1, n=0, Ar1, Ar2, Ar3 and X2 are C6-50 aryl or C4-50 heteroaryl, provided that Ar1 and Ar2, or Ar3 and X2 may form together a ring; X1=C6-50 arylene; R1, R2, R4, R5 and R7 are H, halogen, amino, C1-18 alkyl, C1-18 alkoxy, C6-50 aryl or C4-50 heteroaryl, R3 and R6 are H, halogen, C1-18 alkyl, C1-18 alkoxy, C6-50 aryl or C4-50 heteroaryl; when m=0, n=1-3, Ar3, Ar4 and Ar5 are C6-50 aryl or C4-50 heteroaryl, Ar4 and Ar5 may form together a ring; X1=C1-18 alkyl, C6-50 aryl or C4-50 heteroaryl; X2=C6-50 arylene; R1-R7 are H, halogen, C1-18 alkyl, C1-18 alkoxy, C6-50 aryl or C4-50 heteroaryl; when m=0, n=0, X1=C1-18 alkyl, C6-50 aryl or C4-50 heteroaryl; Ar3 and X2 are C6-50 aryl or C4-50 heteroaryl; R2=H, halogen, C1-18 alkyl, C1-18 alkoxy; R1 and R3-R7 are H, halogen, C1-18 alkyl, C1-18 alkoxy, C6-50 aryl or C4-50 heteroaryl. The carbazole compound is suitable for an organic EL device.
    Type: Grant
    Filed: October 20, 2010
    Date of Patent: May 16, 2017
    Assignee: TOSOH CORPORATION
    Inventors: Naoki Matsumoto, Takanori Miyazaki, Shinichi Ishikawa
  • Patent number: 9608207
    Abstract: An organic electroluminescence element that uses a compound expressed by the following general formula has low inter-molecular interaction and high orientation during vapor deposition, and by using compounds that are resistant to aggregation, luminous efficiency is high, and there is little change in chromaticity accompanying drive deterioration (either V1 or W1 and either V2 or W2 form rings, the rings formed by V1 and V2 are six-membered rings, and the rings formed by W1 and W2 are five-membered rings; A2 to A4 and A6 to A8 represent CRZ or N, and RZ represents a hydrogen atom or a substituent; and R2, R3, R7, and R8 represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom [sic], or a deuterium atom.).
    Type: Grant
    Filed: April 11, 2012
    Date of Patent: March 28, 2017
    Assignee: UDC Ireland Limited
    Inventors: Koji Takaku, Tetsu Kitamura, Toru Watanabe, Yasunori Yonekuta
  • Patent number: 9556209
    Abstract: The present invention refers to a process for the ruthenium-catalyzed trans-selective hydrostannation of alkynes and the so-obtained products. The inventive process makes use of a tin hydride which is reacted with an alkyne in the presence of a cyclopentadienyl-coordinated ruthenium catalyst.
    Type: Grant
    Filed: October 14, 2014
    Date of Patent: January 31, 2017
    Assignee: STUDIENGESELLSCHAFT KOHLE MBH
    Inventors: Alois Fürstner, Stephan Rummelt
  • Patent number: 9523031
    Abstract: Provided is an organic electroluminescence device having high luminous efficiency, high heat resistance and an extremely long lifetime. The organic electroluminescence device of the present invention includes an organic thin film layer composed of one or more layers containing at least a light emitting layer is interposed between a cathode and an anode. The light emitting layer includes a compound containing a condensed ring and a luminescent metal complex capable of emitting light having a red-based color. It is preferable that the compound containing a condensed ring includes a host material, while the luminescent metal complex capable of emitting light having a red-based color includes a phosphorescent dopant.
    Type: Grant
    Filed: May 6, 2005
    Date of Patent: December 20, 2016
    Assignee: IDEMITSU KOSAN CO., LTD.
    Inventors: Kiyoshi Ikeda, Mitsunori Ito, Takashi Arakane
  • Patent number: 9450188
    Abstract: An object is to provide a novel carbazole derivative that has an excellent carrier-transport property and can be suitably used for a transport layer or as a host material of a light-emitting element. Another object is to provide an organic semiconductor material and a light-emitting element material each using the carbazole derivative. As the carbazole derivative that can achieve the above objects, a carbazole derivative in which a carbazolyl group whose either 2- or 3-position of carbazole is substituted by the 4-position of a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to aromatic hydrocarbon that has 14 to 70 carbon atoms and includes a condensed tricyclic ring, a condensed tetracyclic ring, a condensed pentacyclic ring, a condensed hexacyclic ring, or a condensed heptacyclic ring has been able to be synthesized.
    Type: Grant
    Filed: February 3, 2014
    Date of Patent: September 20, 2016
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Hiroki Suzuki, Kyoko Takeda, Sachiko Kawakami, Tsunenori Suzuki, Satoshi Seo, Nobuharu Ohsawa
  • Patent number: 9318711
    Abstract: The organic EL material is represented by Formula (1): where X1 to X4 are each independently a nitrogen (N) atom or a carbon atom that is monovalently bonded to R1(C—R1), R1 is a hydrogen atom, a halogen atom, an aryl group having 6 to 18 carbon atoms, a hetero aryl group having 6 to 18 carbon atoms, or an alkyl group having 1-12 carbon atoms, R2 to R10 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, or hetero aryl group having 6 to 30 carbon atoms, and at least one of X1 to X4 is a nitrogen atom.
    Type: Grant
    Filed: November 20, 2013
    Date of Patent: April 19, 2016
    Assignee: SAMSUNG DISPLAY CO., LTD.
    Inventor: Hiroaki Itoi
  • Patent number: 9306171
    Abstract: A material for organic electroluminescence device having a specific central skeleton to which a cyano-substituted aromatic hydrocarbon group or a cyano-substituted heterocyclic group is bonded at its specific position is described. Further described is an organic electroluminescence device including an organic thin film layer between an anode and a cathode. The organic thin film layer include an light emitting layer and at least one layer of the organic thin film layer contains the material for organic electroluminescence device. The material for organic electroluminescence device realizes an organic electroluminescence device with good emission efficiency.
    Type: Grant
    Filed: December 5, 2012
    Date of Patent: April 5, 2016
    Assignee: IDEMITSU KOSAN CO., LTD.
    Inventors: Yumiko Mizuki, Mitsunori Ito, Tetsuya Inoue, Kumiko Hibino, Kazuki Nishimura, Kei Yoshida
  • Patent number: 9174927
    Abstract: A novel stilbene derivative is provided with motivation of providing a blue emissive material showing excellent color purity. The use of the stilbene derivative of the present invention allows the fabrication of a blue-emissive light-emitting element with excellent color purity. The invention also includes an electronic device equipped with a display portion in which the stilbene derivative is employed. The stilbene derivative of the present invention is represented by formula (1), in which Ar1 and Ar2 may form a 5-membered ring by being directly bonded to each other. In formula (1), A11 represents any one of substituents represented by general formulas (1-1) to (1-3). The variables shown in formula (1) and (1-1) to (1-3) are as defined in the specification.
    Type: Grant
    Filed: April 16, 2014
    Date of Patent: November 3, 2015
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Masakazu Egawa, Harue Osaka, Sachiko Kawakami, Nobuharu Ohsawa, Satoshi Seo, Ryoji Nomura
  • Patent number: 9172045
    Abstract: A 4-aminocarbazole compound represented by formula (1): wherein Ar1-Ar4 represent substituted or unsubstituted aryl, thienyl, pyridyl, benzothienyl, dibenzothienyl, dibenzofuranyl, 4-carbazolyl, dibenzothienylphenyl, dibenzofuranylphenyl or 9-carbazolylphenyl group; R1-R7 represent substituted or unsubstituted aryl, heteroaryl or heteroarylphenyl group, or alkyl, alkoxy, cyano group, or hydrogen or halogen atom; n is integer of 0-2; and X represents substituted or unsubstituted (n+1)-valent aromatic hydrocarbon, heteroaromatic or heteroarylphenyl group. The 4-aminocarbazole compound provides an organic EL device exhibiting enhanced emitting efficiency and durability.
    Type: Grant
    Filed: October 25, 2012
    Date of Patent: October 27, 2015
    Assignee: TOSOH CORPORATION
    Inventors: Naoki Matsumoto, Takanori Miyazaki
  • Patent number: 9172047
    Abstract: A hole transport material for the organic electroluminescence device, the hole transport material being represented by the following Formula 1,
    Type: Grant
    Filed: January 15, 2014
    Date of Patent: October 27, 2015
    Assignee: SAMSUNG DISPLAY CO., LTD.
    Inventor: Hiroaki Itoi
  • Patent number: 9150551
    Abstract: A carbazole compound in which the 2-position of a dibenzofuran skeleton or a dibenzothiophene skeleton is bonded to the 3-position of a carbazole skeleton and nitrogen of the carbazolyl group is bonded to the 9- or 10-position of an anthracene skeleton directly or via a phenylene group was able to be synthesized. It was found out that the carbazole compound has an excellent carrier-transport property, favorable film quality, and a wide band gap, and can be suitably used as a light-emitting element material and an organic semiconductor material.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: October 6, 2015
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Hiroki Suzuki, Harue Osaka, Tsunenori Suzuki
  • Patent number: 9147848
    Abstract: The invention relates to solution-processable, p-type, low-optical gap oligothiophene compounds for use in solar cell application, comprising at least one thiophene-containing group, at least one electron-withdrawing dicyanovinyl or tricyanovinyl group, and at least one electron-donating diphenylaminofluorenyl or N-alkylcarbazole group.
    Type: Grant
    Filed: January 29, 2015
    Date of Patent: September 29, 2015
    Assignee: Nano and Advanced Materials Institute Limited
    Inventors: Ricky Man-Shing Wong, Weifeng Zhang, Lei Guo
  • Patent number: 9133173
    Abstract: To provide a novel carbazole compound that has an excellent carrier-transport property and can be used for a transport layer or as a host material in a light-emitting element. Further, to provide an organic semiconductor material and a material for a light-emitting element using the carbazole compound. A carbazole compound in which the 4-position of a dibenzothiophene skeleton or a dibenzofuran skeleton is substituted with the 2- or 3-position of a carbazole skeleton directly or via an arylene group can be synthesized. The carbazole compound is found to have a suitable carrier-transport property, a good film quality, and be used suitably as a material of a light-emitting element and an organic semicondcutor material. Note that nitrogen of the carbazole skeleton is substituted with any of a phenyl group, a biphenyl group, and a naphthyl group.
    Type: Grant
    Filed: October 12, 2011
    Date of Patent: September 15, 2015
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Harue Osaka, Satoko Shitagaki, Hiromi Nowatari, Nobuharu Ohsawa
  • Publication number: 20150144938
    Abstract: A compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display device including the organic light emitting diode are disclosed and the compound for an organic optoelectronic device represented by a combination of the following Chemical Formulae 1 and 2 provides an organic light emitting diode having life-span characteristics due to excellent electrochemical and thermal stability, and high luminous efficiency at a low driving voltage.
    Type: Application
    Filed: February 4, 2015
    Publication date: May 28, 2015
    Inventors: Han-Ill LEE, Dong-Wan RYU, Sung-Hyun JUNG, Mi-Young CHAE, Dal-Ho HUH, Jin-Seok HONG, Jun-Seok KIM, Dong-Kyu RYU, Yu-Na JANG, Young-Kyoung JO
  • Patent number: 9040719
    Abstract: A carbazole derivative represented by the general formula (1) is provided. In the formula, Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; ? and ? independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.
    Type: Grant
    Filed: August 7, 2013
    Date of Patent: May 26, 2015
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Hiroko Nomura, Harue Osaka, Takahiro Ushikubo, Satoshi Seo
  • Patent number: 9040718
    Abstract: Compounds (including polymers) for use in hybrid host materials which can be used in electroluminescent devices. The compounds comprise at least one electron-transporting moiety and at least one hole-transporting moiety which are joined by a flexible linker. Hybrid host materials comprising the compounds exhibit stability against phase separation, elevated glass transition temperature, morphological stability against crystallization, and isolation of the electron transporting moiety and hole transporting moiety ?-systems.
    Type: Grant
    Filed: January 22, 2010
    Date of Patent: May 26, 2015
    Assignee: The University of Rochester
    Inventors: Shaw H. Chen, Lichang Zeng, Thomas Yung-Hsin Lee
  • Patent number: 9040172
    Abstract: The present invention describes novel indenofluorene derivatives which can preferably be employed as matrix materials for phosphorescent dopants or as electron-transport materials, in particular for use in the emission and/or charge-transport layer of electroluminescent devices. The invention furthermore relates to polymers which comprise these compounds as structural units and to a process for the preparation of the compounds according to the invention and to electronic devices which comprise same.
    Type: Grant
    Filed: June 1, 2010
    Date of Patent: May 26, 2015
    Assignee: Merck Patent GmbH
    Inventors: Amir Hossain Parham, Christof Pflumm, Teresa Mujica-Fernaud, Arne Buesing, Holger Heil
  • Publication number: 20150141642
    Abstract: A light-emitting material containing a compound represented by the following general formula in a light-emitting layer has high light emission efficiency. In the following general formula, R1 to R10 represent a hydrogen atom or a substituent, provided that at least one of R1 to R10 represents an aryl group, a diarylamino group or a 9-carbazolyl group.
    Type: Application
    Filed: March 15, 2013
    Publication date: May 21, 2015
    Applicant: KYUSHU UNIVERSITY NATIONAL UNIVERSITY CORPORATION
    Inventors: Chihaya Adachi, QiSheng Zhang, Kei Sakanoue, Shuzo Hirata
  • Publication number: 20150141664
    Abstract: The invention relates to solution-processable, p-type, low-optical gap oligothiophene compounds for use in solar cell application, comprising at least one thiophene-containing group, at least one electron-withdrawing dicyanovinyl or tricyanovinyl group, and at least one electron-donating diphenylaminofluorenyl or N-alkylcarbazole group.
    Type: Application
    Filed: January 29, 2015
    Publication date: May 21, 2015
    Inventors: Ricky Man-Shing Wong, Weifeng Zhang, Lei Guo