Patents Assigned to Hodogaya Chemical Co., Ltd.
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Patent number: 9525140Abstract: A problem of the invention is to provide an organic EL device having a high efficiency, a low driving voltage and a long life, by combining various materials for organic EL device, which are excellent in an injection or transportation performance of holes or electrons, and in stability and durability in a thin film, so as to enable the respective materials to effectively reveal their characteristics. The invention relates to an organic electroluminescent device including at least an anode electrode, a hole-injecting layer, a hole-transporting layer, an emitting layer, an electron-transporting layer and a cathode electrode in this order, in which the hole-injecting layer contains an arylamine compound having, in its molecule, a structure in which three or more triphenylamine structures are connected through a single bond or a hetero atom-free divalent group; and the hole-transporting layer contains an arylamine compound having two triphenylamine structures in its molecule.Type: GrantFiled: October 2, 2013Date of Patent: December 20, 2016Assignee: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa Yokoyama, Shigeru Kusano, Shuichi Hayashi
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Publication number: 20160351823Abstract: According to the present invention, there are provided a benzofuroindole derivative represented by the following general formula (1); and an organic EL device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the above derivative is used as a constituent material for the at least one organic layer. The benzofuroindole derivative of the present invention is useful as a constituent material for a hole injection layer, a hole transport layer, an electron blocking layer or a luminous layer of an organic EL device. It has excellent electron blocking capability, is stable in a thin film state, and excels in heat resistance. Thus, the organic EL device of the present invention, prepared using such a benzofuroindole derivative, is high in luminous efficiency and power efficiency, thereby lowering the practical driving voltage of the device. The device can also lower light emission starting voltage, and improve durability.Type: ApplicationFiled: February 12, 2015Publication date: December 1, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Makoto NAGAOKA, Kouki KASE, Keigo NAITO, Kanae OTSUKA, Shigeru KUSANO
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Patent number: 9444055Abstract: An organic electroluminescent device comprising, between an anode and a cathode, a hole-transporting layer, a luminous layer and an electron-transporting layer, wherein the hole-transporting layer contains an arylamine compound (X) having a molecular structure to which three or more triphenylamine skeletons are singly bonded or bonded through a divalent hydrocarbon group and an arylamine compound (Y) having a molecular structure to which two triphenylamine skeletons are singly bonded or bonded through the divalent hydrocarbon group. The device excels in hole and electron injection/transport property, stability and durability in the form of thin films, and is highly efficient, becomes luminous on a low driving voltage, and has a long life.Type: GrantFiled: February 24, 2012Date of Patent: September 13, 2016Assignee: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa Yokoyama, Shuichi Hayashi, Eiji Takahashi, Shigeru Kusano
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Publication number: 20160254458Abstract: According to the present invention, there are provided a benzopyridoindole derivative represented by the following general formula (1); and an organic EL element including a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the above derivative is used as a constituent material for the at least one organic layer. The benzopyridoindole derivative of the present invention is excellent in electron injection/transport performance, has hole blocking capability, is highly stable in a thin film state, and excels in various characteristics. Thus, it is useful as a material for an organic EL element with a high efficiency, a low driving voltage, and high durability.Type: ApplicationFiled: September 1, 2014Publication date: September 1, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Makoto NAGAOKA, Kouki KASE, Shigeru KUSANO, Teruaki KOIZUMI
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Publication number: 20160209769Abstract: The present invention provides a toner that includes a charge control agent containing one or two or more resorcin derivatives represented by the following formula (1), a colorant, and a binder resin.Type: ApplicationFiled: September 24, 2014Publication date: July 21, 2016Applicant: HODOGAYA CHEMICAL CO., LTDInventors: Masaki OKUBO, Motonori TSUJI, Masami ITO, Masaya TOJO, Masafumi ASAKAI, Tetsuya YOSHIDA
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Publication number: 20160164001Abstract: A Benzotriazole derivative represented by the following general formula (1), wherein, Ar1 is a monovalent aromatic hydrocarbon group or aromatic heterocyclic group, Ar2 is a hydrogen atom, a deuterium atom, or a monovalent aromatic hydrocarbon group or aromatic heterocyclic group, A is a divalent aromatic hydrocarbon group or aromatic heterocyclic group, B is a divalent condensed polycyclic aromatic hydrocarbon group or a single bond, and C is a monovalent aromatic heterocyclic group, and wherein if A is a phenylene group, B is a divalent condensed polycyclic aromatic hydrocarbon group or C is a monovalent aromatic heterocyclic group other than a pyridyl group.Type: ApplicationFiled: July 24, 2014Publication date: June 9, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Makoto NAGAOKA, Shigetaka NUMAZAWA, Kanae OTSUKA, Shigeru KUSANO
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Publication number: 20160155955Abstract: Dicarbazole derivatives represented by the following general formula (1), wherein X is an oxygen atom or a sulfur atom, Ar1 and Ar2 are aromatic hydrocarbon groups or aromatic heterocyclic groups, R1 to R12 are hydrogen atoms, deuterium atoms, fluorine atoms, chlorine atoms, cyano groups, nitro groups, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkyloxy groups having 1 to 6 carbon atoms, cycloalkyloxy groups having 5 to 10 carbon atoms, aromatic hydrocarbon groups, aromatic heterocyclic groups, aryloxy groups or disubstituted amino groups having aromatic hydrocarbon groups or aromatic heterocyclic groups as substituents bonded to the nitrogen atom.Type: ApplicationFiled: June 9, 2014Publication date: June 2, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa YOKOYAMA, Daizou KANDA, Shuichi HAYASHI
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Publication number: 20160152831Abstract: The present invention relates to a colorant for hair dyeing containing a compound represented by the following general formula (I), a composition for hair dyeing containing the same, and a hair dyeing method: (in the formula, R1, R2 and R3 each independently represent a hydrogen atom, a linear or branched alkyl group having from 1 to 6 carbon atoms, or a linear or branched alkoxy group having from 1 to 6 carbon atoms, and An? represents an inorganic anion or an organic anion).Type: ApplicationFiled: June 10, 2014Publication date: June 2, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Mitsuhiro AKIBA, Kenichiro SUZUKI, Michihiro GONDA, Masatoshi ISOBE
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Publication number: 20160126468Abstract: According to the present invention, there are provided an indenoindole derivative represented by the following general formula (1); and an organic electroluminescent element including a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the above compound is used as a constituent material for the at least one organic layer. The indenoindole derivative of the present invention provides an organic compound, which is excellent in hole injection/transport performance, has electron blocking capability, is highly stable in a thin film state, and excels in heat resistance, as a material for a high efficiency, high durability organic electroluminescent element. An organic electroluminescent element formed using this compound is highly efficient and highly durable.Type: ApplicationFiled: June 4, 2014Publication date: May 5, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Makoto NAGAOKA, Shigetaka NUMAZAWA, Norimasa YOKOYAMA, Si In KIM, Shigeru KUSANO
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Patent number: 9306175Abstract: A high-efficiency, high-durability organic electroluminescent device, particularly a phosphorescent organic electroluminescent device is provided by using an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has high triplet exciton confining capability with an electron blocking ability, and that has high stability in the thin-film state and high luminous efficiency. The organic electroluminescent device includes a pair of electrodes, and a plurality of organic layers sandwiched between the pair of electrodes and including a phosphorescent light-emitting material-containing light emitting layer and a hole transport layer, wherein a compound of the following general formula (1) having a carbazole ring structure is used as a constituent material of the hole transport layer.Type: GrantFiled: October 22, 2010Date of Patent: April 5, 2016Assignee: Hodogaya Chemical Co., Ltd.Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kazunori Togashi, Shigeru Kusano, Eiji Takahashi
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Patent number: 9306174Abstract: A high-efficiency, high-durability organic electroluminescent device, particularly a phosphorescent organic electroluminescent device is provided by using an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has high triplet exciton confining capability with an electron blocking ability, and that has high stability in the thin-film state and high luminous efficiency. The organic electroluminescent device includes a pair of electrodes, and a plurality of organic layers sandwiched between the pair of electrodes and including a light emitting layer and an electron blocking layer, wherein a compound of the following general formula (1) having a carbazole ring structure is used as a constituent material of the electron blocking layer and the light emitting layer.Type: GrantFiled: October 22, 2010Date of Patent: April 5, 2016Assignee: Hodogaya Chemical Co., Ltd.Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kazunori Togashi, Shigeru Kusano, Eiji Takahashi
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Publication number: 20160087215Abstract: Pyrimidine derivatives of the present invention are represented by the following general formula (1), wherein W, X, Y and Z are carbon atoms or nitrogen atoms under the condition that only any one is a nitrogen atom to which none of the groups R6 to R9 are bonded, A and B are single bonds, divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups, Ar1 and Ar2 are monovalent aromatic hydrocarbon groups or monovalent aromatic heterocyclic groups, and R1 to R9 are hydrogen atoms, deuterium atoms, fluorine atoms, chlorine atoms, cyano groups, alkyl groups having 1 to 6 carbon atoms, monovalent aromatic hydrocarbon groups or monovalent aromatic heterocyclic groups. The compound excels in electron injection/transporting capability, features high hole-blocking power and high stability in the form of a thin film, and can be favorably used as a material for producing highly efficient and durable organic EL devices.Type: ApplicationFiled: May 15, 2014Publication date: March 24, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa YOKOYAMA, Naoaki KABASAWA, Shuichi HAYASHI, Jeong-Soo KIM
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Patent number: 9238624Abstract: A method of producing an aromatic amino compound by using a primary or secondary amine compound having an aromatic ring group and a halogenated aromatic compound as starting materials, reacting the amine compound with the halogenated aromatic compound in the presence of a copper catalyst and a base so as to produce the aromatic amino compound having a structure in which an aromatic ring group derived from the halogenated aromatic compound is coupled to the amino group of the amine compound, wherein the amine compound and the halogenated aromatic compound are reacted together under a condition where an aromatic oxycarboxylic acid having a hydroxyl group and a hydroxycarbonyl group that are bonded to neighboring carbon atoms, is made present together with the copper catalyst and the base.Type: GrantFiled: December 2, 2013Date of Patent: January 19, 2016Assignee: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kazunori Togashi
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Publication number: 20160005982Abstract: Naphthotriazole derivatives represented by the following general formula (1), wherein, Ar1 is an aromatic hydrocarbon group or an aromatic heterocyclic group, and A is a group that contains an aromatic heterocyclic group. The compound features excellent electron injection/transporting capability, a high hole-blocking power and a high stability in the form of a thin film, and can be used as a material for producing highly efficient and highly durable organic electroluminescent devices.Type: ApplicationFiled: February 20, 2014Publication date: January 7, 2016Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Makoto NAGAOKA, Shigetaka NUMAZAWA, Mari TORIYA, Shingo OZAWA, Shigeru KUSANO
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Patent number: 9196839Abstract: There is provided an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has an electron blocking ability and a highly stable thin-film state with excellent heat resistance. The compound of the present invention is an arylamine compound having a triphenylamine structure. The arylamine compound is used as a constituent material of at least one organic layer in an organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.Type: GrantFiled: January 25, 2011Date of Patent: November 24, 2015Assignee: Hodogaya Chemical Co., Ltd.Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kouki Kase, Shingo Ozawa, Shigeru Kusano
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Patent number: 9196837Abstract: An organic compound with excellent characteristics excelling in hole-injecting/transporting performance and having electron blocking ability, high stability in a thin-film state and high luminous efficiency is provided as material for an organic electroluminescent device. The compound of a general formula (1) having an indenocarbazole ring structure is used as a constituent material of at least one organic layer in the organic electroluminescent device that includes a pair of electrodes and one or more organic layers sandwiched between the pair of electrodes.Type: GrantFiled: July 29, 2011Date of Patent: November 24, 2015Assignee: Hodogaya Chemical Co., Ltd.Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kazunori Togashi, Kouki Kase, Eiji Takahashi
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Publication number: 20150287920Abstract: An organic electroluminescent device having a capping layer composed of material having a high refractive index that involves only small differences in refractive indices measured in the blue, green, and red wavelength regions, excelling in thin film stability and durability and having no absorption in the respective wavelength ranges of blue, green, and red is provided to improve device characteristics of the organic electroluminescent device, particularly to greatly improve the coupling-out efficiency.Type: ApplicationFiled: March 14, 2013Publication date: October 8, 2015Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Makoto Nagaoka, Shuichi Hayashi, Motonori Tsuji, Yoshikazu Aoki
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Patent number: 9141014Abstract: The present invention is a toner for developing electrostatic charge image containing a wax derived from a plant cholesterol, an electric charge-controlling agent, a coloring agent and a binding resin. The toner is suited for use in the electromagnetic induction-heated fixing system which is capable of heating the heating member up to a predetermined fixing temperature in a short period of time, makes it possible to maintain images free of irregular luster or fouling for extended periods of time and is, further, suited for being fixed at a low temperature.Type: GrantFiled: March 27, 2012Date of Patent: September 22, 2015Assignee: HODOGAYA CHEMICAL CO., LTD.Inventors: Masaki Okubo, Tatsuji Orita, Hideyuki Otsuka, Kenichi Sato, Kanae Hiraishi
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Publication number: 20150249218Abstract: An organic compound with excellent characteristics excelling in hole injecting and transporting performance and having an electron-blocking ability, high stability in a thin film state and excellent heat resistance is provided as a material for an organic electroluminescent device of high efficiency and high durability, and the organic electroluminescent device of high luminous efficiency and high durability is provided using this compound. The compound of a general formula (1) having an indenoacridan ring structure is used as a constituent material of at least one organic layer in the organic electroluminescent device that includes a pair of electrodes and one or more organic layers sandwiched between the pair of electrodes.Type: ApplicationFiled: August 27, 2013Publication date: September 3, 2015Applicant: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa Yokoyama, Daizou Kanda, Shuichi Hayashi
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Patent number: 9123897Abstract: Benzotriazole derivatives represented by the following general formula (1), wherein Ar1 and Ar2 are, for example, aromatic hydrocarbon groups or aromatic heterocyclic ring groups, and A is a group including a pyridine ring. The compounds excel in electron injection/transport capability, feature a high hole-blocking power and a high stability in their thin-film form, and are useful as materials for producing highly efficient and highly durable organic electroluminescent devices.Type: GrantFiled: October 5, 2012Date of Patent: September 1, 2015Assignee: HODOGAYA CHEMICAL CO., LTD.Inventors: Norimasa Yokoyama, Shigetaka Numazawa, Shirou Irisa, Shuichi Hayashi