Patents Assigned to Hodogaya Chemical Co., Ltd.
  • Patent number: 9056884
    Abstract: A process for producing a charge control agent comprising an azo-based iron complex salt compound as an effective component, comprises: synthesizing a monoazo compound through diazotization coupling; and ironing the monoazo compound by using an ironizing agent such as ferric chloride to produce an azo-based iron complex salt compound represented by the following formula. The ironization reaction of the monoazo compound is carried out while pH is kept at 7.0 to 8.0. Since the above azo-based iron complex salt compound having high purity can be obtained at a high yield, it can be used as a charge control agent directly and a special purification step can be eliminated, thereby making it possible to greatly cut the production cost.
    Type: Grant
    Filed: March 5, 2013
    Date of Patent: June 16, 2015
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Atsushi Takesue, Yoshihiko Abe, Hideyuki Otsuka, Jun Watanabe, Shunsuke Saitoh, Kanae Hiraishi
  • Patent number: 9005776
    Abstract: A compound having a benzotriazole ring structure and a formula (1): wherein Ar is a substituted or unsubstituted aromatic hydrocarbon group, aromatic heterocyclic group, or condensed polycyclic aromatic group; A and B are the same as or different from each other and each represent a hydrogen atom or a monovalent group of formula (2), provided that A and B are not simultaneously hydrogen atoms: wherein R1 to R8 are the same as or different and each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or condensed polycyclic aromatic group; m is an integer of 0, 1 or 2; X represents a carbon atom or a nitrogen atom; when X is a nitrogen atom, the nitrogen atom does not have substituents or bonding groups of R1, R2, R3 and R4; and when m is 2, a plurality of R1, R2, R3, R4 and X each are the
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: April 14, 2015
    Assignees: Hodogaya Chemical Co., Ltd., Shinshu University
    Inventors: Norimasa Yokoyama, Shuichi Hayashi, Naoaki Kabasawa, Yoshio Taniguchi, Musubu Ichikawa, Shunji Mochiduki
  • Patent number: 8962866
    Abstract: Provided by the present invention is a surface-modified silica powder, characterized in that the said powder is obtained by surface treatment of a silica powder with one or two or more of a compound (A) and with an aminosilane (B), wherein the fixing rate of the compound (A) and the aminosilane (B) is a total of 50% or more, the hydrophobic rate is 80% or more, and the triboelectrostatic charge amount is 200 ?C/g or less in its absolute value. The surface-modified silica powder of the present invention can stabilize many properties including fluidity and electrostatic properties while can significantly reduce problems such as fogging and decrease in image quality without significantly deteriorating characteristics of a developing agent and so forth when this is used as an external additive.
    Type: Grant
    Filed: February 3, 2012
    Date of Patent: February 24, 2015
    Assignees: Nippon Aerosil Co., Ltd., Hodogaya Chemical Co., Ltd.
    Inventors: Yuki Amano, Naohiro Naito, Hisao Okada, Masaki Okubo, Yoshikazu Aoki, Hideyuki Otsuka
  • Publication number: 20150034924
    Abstract: Triphenylene derivatives represented by the following general formula (1), wherein Ar1 and Ar2 are aromatic groups. The compounds have a structure in which an aromatic tertiary amine is introduced into a triphenylene ring. Owing to this structure, the compounds exhibit (A) favorable hole injection property, (B) large hole mobility, (C) excellent electron blocking power, (D) stability in their thin-film form, and (E) excellent heat resistance. The compounds are useful as hole-transporting materials for use in the organic EL devices.
    Type: Application
    Filed: October 12, 2012
    Publication date: February 5, 2015
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Norimasa Yokoyama, Naoaki Kabasawa, Hiroshi Ookuma, Shuichi Hayashi, Eiji Takahashi
  • Patent number: 8927119
    Abstract: There is provided an organic compound having excellent characteristics, including excellent electron-injecting/transporting performance, hole blocking ability, and high stability in the thin-film state, for use as material of an organic electroluminescent device having high efficiency and high durability. There is also provided a high-efficient and high-durable organic electroluminescent device using the compound. The compound is represented by general formula (1) having a substituted anthracene ring structure and a pyridoindole ring structure. The organic electroluminescent device includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes, and the compound is used as a constituent material of at least one organic layer.
    Type: Grant
    Filed: July 28, 2010
    Date of Patent: January 6, 2015
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Shuichi Hayashi, Naoaki Kabasawa, Daizou Kanda, Shigeru Kusano
  • Publication number: 20140374721
    Abstract: 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: Application
    Filed: October 5, 2012
    Publication date: December 25, 2014
    Applicant: HODOGAYA CHEMICAL CO., LTD
    Inventors: Norimasa Yokoyama, Shigetaka Numazawa, Shirou Irisa, Shuichi Hayashi
  • Patent number: 8900785
    Abstract: A charge control agent comprises a barbituric acid derivative represented by the following general formula (1): wherein R1 to R8 are alkyl groups, cycloalkyl groups or aryl groups, V, W, X, Y and Z are carbon atoms or nitrogen atoms, at least two of which being carbon atoms, and p, q, r, s and t are the numbers of 0 or 1.
    Type: Grant
    Filed: September 2, 2011
    Date of Patent: December 2, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Ikuo Kimura, Masami Ito, Masaya Tojou, Kanae Hiraishi, Masafumi Asakai
  • Publication number: 20140339518
    Abstract: An improved OLED includes an emitter layer disposed between a cathode and an anode where the emitter layer includes a host material and a phosphorescent emitter material. A first hole transport layer is disposed between the emitter layer and the anode and a second hole transport layer is disposed between the first hole transport layer and the anode. The first hole transport layer includes a first hole transport material that is a carbazole type compound and the second hole transport layer includes a second hole transport material that is different from the first hole transport material. The phosphorescent emitter material includes a phosphorescent organometallic compound that is a heteroleptic compound represented by the formula L2MX, LL?MX, LL?L?M, or LMXX?, wherein L, L?, L?, X, and X? are inequivalent, bidentate ligands and M is a metal that forms octahedral complexes, wherein L, L?, and L? are monoanionic inequivalent bidentate ligands coordinated to M through an sp2 hybridized carbon and a heteroatom.
    Type: Application
    Filed: August 5, 2011
    Publication date: November 20, 2014
    Applicants: HODOGAYA CHEMICAL CO., LTD., UNIVERSAL DISPLAY CORPORATION
    Inventors: Hitoshi Yamamoto, Michael Stewart Weaver, Norimasa Yokoyama, Makoto Nagaoka, Naoaki Kabasawa
  • Patent number: 8852759
    Abstract: An organic compound with characteristics excelling in hole-injecting/transporting performance and having an electron blocking ability, a highly stable thin-film state, and excellent heat resistance is provided as material for an organic electroluminescent device of high efficiency and high durability, and the organic electroluminescent device of high efficiency and high durability is provided using this compound. The compound of a general formula (Chemical Formula 1) having a substituted acridan 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: Grant
    Filed: June 3, 2011
    Date of Patent: October 7, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Makoto Nagaoka, Naoaki Kabasawa, Eiji Takahashi
  • Patent number: 8834579
    Abstract: The present invention relates to an azo dye composition for hair dyeing that has an excellent performance as a dye for hair dyeing and proves negative in the Ames test, and also relates to a method for producing the composition. An object of the present invention is to develop a purification method for a dye composition for hair dyeing mainly containing an azo dye and proving negative in the Ames test, and to provide the dye composition for hair dyeing that is produced by applying the purification method and indicates negative in the Ames test. The dye composition for hair dyeing contains, as a main component, the azo dye having trimethylammonio, and the dye composition for hair dyeing is characterized in that the result of the Ames test is negative.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: September 16, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Masatoshi Isobe, Kenichiro Suzuki, Mitsuhiro Akiba
  • Patent number: 8808951
    Abstract: An object of the present invention is to provide an electrophotographic photosensitive body having improved electrophotographic characteristics such as sensitivity and residual potential and also having excellent durability. The present invention provides an electrophotographic photosensitive body having a layer containing at least one specific p-terphenyl compound and at least one polycarbonate resin represented by the general formula (I): in a mass ratio of the p-terphenyl compound to the polycarbonate resin within the range of 2:8 to 7:3.
    Type: Grant
    Filed: June 5, 2013
    Date of Patent: August 19, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Katsumi Abe, Atsushi Takesue, Takehiro Nakajima, Makoto Koike, Shinya Nagai
  • Publication number: 20140225100
    Abstract: An organic electroluminescent device having a capping layer composed of material having a high refractive index, 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 light extraction efficiency. The organic electroluminescent device has at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode, and the capping layer in this order, wherein the capping layer contains an arylamine compound (X) having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom.
    Type: Application
    Filed: September 6, 2012
    Publication date: August 14, 2014
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Norimasa Yokoyama, Shuichi Hayashi, Shigeru Kusano
  • Patent number: 8790855
    Abstract: The present invention provides a charge control agent containing, as an active substance(s), one or two or more thiazolidinedione derivatives represented by the following formula (1), where R1 represents a hydrogen atom, etc.; R2 represents a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent, etc.; R3 to R7, which may be identical to or different from each other, represent a hydrogen atom, a chlorine atom, a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent, etc., and may be joined to each other to form a ring; and V, W, X, Y and Z represent a carbon atom or a nitrogen atom, and 0 to 3 of any of V, W, X, Y and Z are nitrogen atoms which do not have the substituents of R3 to R7.
    Type: Grant
    Filed: September 1, 2011
    Date of Patent: July 29, 2014
    Assignee: Hodogaya Chemical Co., Ltd
    Inventors: Ikuo Kimura, Motonori Tsuji, Masami Ito, Masaya Tojo, Kanae Hiraishi
  • Publication number: 20140205945
    Abstract: To provide a charge controlling agent for electrophotography, which presents sufficient triboelectric chargeability to a toner, is useful particularly for a color toner and further for a polymerized toner, increases a charge rising rate, has a high electric charge amount, is excellent in charging characteristics, stability over time and environmental stability and yet is safe without posing any problem regarding waste regulations, and a negatively chargeable toner for developing an electrostatic image, which uses such a charge controlling agent and which has a high charging performance.
    Type: Application
    Filed: January 24, 2014
    Publication date: July 24, 2014
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Ikuo KIMURA, Masami ITO, Masaya TOJO, Masafumi ASAKAI
  • Patent number: 8771841
    Abstract: 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: Grant
    Filed: May 15, 2009
    Date of Patent: July 8, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Shigeru Kusano, Shuichi Hayashi
  • Publication number: 20140171628
    Abstract: A process for producing a charge control agent comprising an azo-based iron complex salt compound as an effective component, comprises: synthesizing a monoazo compound through diazotization coupling; and ironing the monoazo compound by using an ironizing agent such as ferric chloride to produce an azo-based iron complex salt compound represented by the following formula. The ironization reaction of the monoazo compound is carried out while pH is kept at 7.0 to 8.0. Since the above azo-based iron complex salt compound having high purity can be obtained at a high yield, it can be used as a charge control agent directly and a special purification step can be eliminated, thereby making it possible to greatly cut the production cost.
    Type: Application
    Filed: March 5, 2013
    Publication date: June 19, 2014
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Atsushi TAKESUE, Yoshihiko ABE, Hideyuki OTSUKA, Jun WATANABE, Shunsuke SAITOH, Kanae HIRAISHI
  • Publication number: 20140163232
    Abstract: 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: Application
    Filed: December 2, 2013
    Publication date: June 12, 2014
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Norimasa YOKOYAMA, Makoto NAGAOKA, Kazunori TOGASHI
  • Patent number: 8748014
    Abstract: The present invention relates to a compound having a substituted anthracene ring structure and a pyridoindole ring structure, which is represented by the following general formula (1) or the following general formula (2); and an organic electroluminescent device having a pair of electrodes and at least one organic layer interposed therebetween, in which the compound having a substituted anthracene ring structure and a pyridoindole ring structure, which is represented by the following general formula (1) or the following general formula (2), is used as a constituent material of the aforementioned at least one organic layer.
    Type: Grant
    Filed: November 10, 2010
    Date of Patent: June 10, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Shuichi Hayashi, Kouki Kase, Hiroshi Ohkuma, Eiji Takahashi, Daizou Kanda
  • Patent number: 8735626
    Abstract: A method of producing an aromatic amino compound using a primary or secondary amine compound and a halogenated aromatic compound as starting materials, and relying upon the Ullmann reaction, the method being capable of obtaining the highly pure aromatic amino compound in high yields and inexpensively. A primary or secondary amine compound having an aromatic ring group and a halogenated aromatic compound as starting materials, are reacted with the halogenated aromatic compound in the presence of copper catalyst and base 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 such that an aromatic oxycarboxylic acid having a hydroxyl group and a hydroxycarbonyl group bonded to neighboring carbon atoms, is present together with the copper catalyst and the base.
    Type: Grant
    Filed: January 25, 2010
    Date of Patent: May 27, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kazunori Togashi
  • Patent number: 8722209
    Abstract: The invention relates to a compound having a pyridoindole ring structure having a substituted pyridyl group of formula (1); and to an organic electroluminescent device comprising a pair of electrodes and at least one organic layer interposed between the electrodes, wherein at least one of the organic layer(s) contains the compound: wherein Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; R1 to R10 may be the same or different from one another and each independently represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Z represents a 6-membered aromatic heterocyclic ring containing one nitrogen atom; and m and n each independently represents an integer of 1 to 3, provided that n is 1 when m is 2 or 3.
    Type: Grant
    Filed: March 14, 2012
    Date of Patent: May 13, 2014
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Shuichi Hayashi, Shigeru Kusano