公开(公告)号：US11084837B2

公开(公告)日：2021-08-10

申请号：US16478417

申请日：2018-03-05

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Toshiyuki Shigetomi ,  Kazuharu Suzuki

IPC: C07F15/00 ,  C23C16/16

Abstract: The present invention relates to a chemical deposition raw material for manufacturing an iridium thin film or an iridium compound thin film by a chemical deposition method, including an iridium complex in which cyclopropenyl or a derivative thereof and a carbonyl ligand are coordinated to iridium. The iridium complex that is applied in the present invention enables an iridium thin film to be manufactured even when a reducing gas such as hydrogen is applied. in which R1 to R3, which are substituents of the cyclopropenyl ligand, are each independently hydrogen, or a linear or branched alkyl group with a carbon number of 1 or more and 4 or less.

公开(公告)号：US10533027B2

公开(公告)日：2020-01-14

申请号：US16060105

申请日：2016-12-22

Applicant: TANAKA KIKINZOKU KOGYO K.K. ,  NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Inventor： Hideo Konno ,  Junichi Taniuchi ,  Ryosuke Harada ,  Toshiyuki Shigetomi ,  Rumi Kobayashi ,  Yasushi Masahiro

IPC: C07F15/00 ,  C09K11/06 ,  H01L51/00 ,  H01L51/50

Abstract: The present invention provides a method for producing a cyclometalated iridium complex by use of a non-chlorine iridium raw material. The method for producing a cyclometalated iridium complex includes producing a cyclometalated iridium complex by reacting a raw material including an iridium compound with an aromatic heterocyclic bidentate ligand capable of forming an iridium-carbon bond, the raw material being non-halogenated iridium having a conjugated base of a strong acid as a ligand. Here, the non-halogenated iridium is preferably one containing a conjugated base of a strong acid having a pKa of 3 or less as a ligand.

公开(公告)号：US09284249B2

公开(公告)日：2016-03-15

申请号：US14438963

申请日：2013-10-17

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Toshiyuki Shigetomi ,  Satoshi Miyazaki ,  Masayuki Saito

IPC: C07C45/80

CPC classification number: C07C45/80 ,  C07C49/12 ,  C07C49/14

Abstract: The present invention provides a method of extracting an asymmetric β-diketone compound from a β-diketone compound containing at least one symmetric β-diketone compound mixed in the asymmetric β-diketone compound, and the method includes the step (A) of adjusting a pH of a mixed solution of the β-diketone compound and water at 11.5 or more and dissolving the β-diketone compound into water to form a β-diketone compound solution and the step (B) of subsequently adjusting the pH of the β-diketone compound solution at 9.5 or less and recovering the asymmetric β-diketone compound of Chemical Formula 1 separated from the β-diketone compound solution. The present invention further includes at least either (a) a step of setting the upper limit of the pH of the mixed solution to 12.5 to form a β-diketone compound solution in the step (A) and bringing the β-diketone compound solution into contact with a hydrophobic solvent or (b) a step of setting the lower limit of the pH of the β-diketone compound solution to 8.0 in the step (B).

Abstract translation: 本发明提供了从含有至少一种混合在不对称 - 二 - 二酮化合物中的对称二酮化合物的β-二酮化合物中提取不对称二酮化合物的方法，该方法包括步骤（A ）将所述二 - 二酮化合物和水的混合溶液的pH调节至11.5以上，并将所述二酮化合物溶解在水中以形成二酮化合物溶液，并且随后调整步骤（B） 将二 - 二酮化合物溶液的pH调节至9.5或更低，并回收分离自二 - 二酮化合物溶液的化学式1的不对称 - 二酮化合物。 本发明还包括（a）将步骤（A）中将混合溶液的pH值的上限设定为12.5以形成步骤（A）中的β-二酮化合物溶液并使该二酮化合物 溶液与疏水性溶剂接触，或（b）在步骤（B）中将β-二酮化合物溶液的pH下限设定为8.0的步骤。

公开(公告)号：US11149045B2

公开(公告)日：2021-10-19

申请号：US16628195

申请日：2018-07-12

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Shigeyuki Ootake ,  Toshiyuki Shigetomi ,  Kazuharu Suzuki

IPC: H01L21/285 ,  C07F15/00 ,  C23C16/18 ,  H01L29/45

Abstract: A raw material for vapor deposition for producing a platinum thin film or a platinum compound thin film by a vapor deposition method. The raw material for vapor deposition includes an organoplatinum compound represented by the following formula, in which a cyclopentene-amine ligand and an alkyl ligand are coordinated to divalent platinum. The organoplatinum compound of the present invention has moderate thermal stability and can respond flexibly to severe film formation conditions, including a wider film formation area, higher throughput, and the like. (In the formula, R1, R2, and R3 are each any one of a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an imino group, a cyano group, and an isocyano group, each having 4 or less carbon atoms, and R4 and R5 are each an alkyl group having 1 or more and 3 or less carbon atoms.)

公开(公告)号：US10815260B2

公开(公告)日：2020-10-27

申请号：US15744751

申请日：2016-08-23

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Toshiyuki Shigetomi ,  Tasuku Ishizaka ,  Tatsutaka Aoyama

IPC: C23C16/16 ,  C07F15/00 ,  C23C16/455 ,  C23C16/18 ,  C09D1/00 ,  C09D5/24 ,  H01L21/285 ,  H01L21/3205

Abstract: The present invention relates to a chemical vapor deposition raw material for producing a ruthenium thin film or a ruthenium compound thin film by a chemical deposition method, the chemical vapor deposition raw material including a dinuclear ruthenium complex in which carbonyl and a nitrogen-containing organic ligand (L) are coordinated to metallically bonded two rutheniums, the dinuclear ruthenium complex being represented by the following formula (1): A raw material according to the present invention is capable of producing a high-purity ruthenium thin film, and has a low melting point and moderate thermal stability. Thus, the raw material according to the present invention is suitable for use in electrodes of various kinds of devices.

公开(公告)号：US10526698B2

公开(公告)日：2020-01-07

申请号：US16277789

申请日：2019-02-15

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Toshiyuki Shigetomi ,  Shunichi Nabeya ,  Kazuharu Suzuki ,  Akiko Kumakura ,  Tatsutaka Aoyama ,  Takayuki Sone

IPC: C23C16/18 ,  C07F13/00 ,  C07F15/00 ,  C07F15/02 ,  C07F15/06 ,  C07F17/00 ,  C07F19/00 ,  C23C16/06 ,  C07F15/04

Abstract: The present invention relates to a chemical deposition raw material including a heterogeneous polynuclear complex in which a cyclopentadienyl and a carbonyl are coordinated to a first transition metal and a second transition metal as central metals, the chemical deposition raw material being represented by the following formula. In the following formula, the first transition metal (M1) and the second transition metal (M2) are mutually different. The number of cyclopentadienyls (L) is 1 or more and 2 or less, and to the cyclopentadienyl is coordinated one of a hydrogen atom and an alkyl group with a carbon number of 1 or more and 5 or less as each of substituents R1 to R5. With the chemical deposition raw material of the present invention, a composite metal thin film or a composite metal compound thin film containing plural metals can be formed from a single raw material.

公开(公告)号：US10407450B2

公开(公告)日：2019-09-10

申请号：US15558011

申请日：2016-05-09

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Toshiyuki Shigetomi ,  Shunichi Nabeya ,  Kazuharu Suzuki ,  Akiko Kumakura ,  Tatsutaka Aoyama ,  Takayuki Sone

IPC: C07F13/00 ,  C07F15/00 ,  C23C16/16 ,  C07F15/06 ,  C07F19/00 ,  C07C251/08 ,  C23C16/18 ,  H01L21/285 ,  H01L21/31 ,  C23C16/06 ,  C23C16/46 ,  H01L21/02

Abstract: A heterogeneous polynuclear complex for use as a raw material in the chemical deposition of composite metal or composite metal thin films with the below formula. In the formula, M1 and M2 are mutually different transition metals, x is an integer of 0 or more and 2 or less, y is in integer of 1 or more and 2 or less, z is an integer of 1 or more and 10 or less, R1 to R4 are each one of a hydrogen atom and an alkyl group with a carbon number of 1 or more and 5 or less, and R5 is a hydrogen atom, a carbonyl, an alkyl group with a carbon number of 1 or more and 7 or less, an allyl group or an allyl derivative. The heterogeneous polynuclear complex allows a composite metal thin film or a composite metal compound thin film containing a plurality of metals to be formed from a single raw material.

公开(公告)号：US10053479B2

公开(公告)日：2018-08-21

申请号：US15109927

申请日：2014-12-16

Applicant: TANAKA KIKINZOKU KOGYO K.K. ,  NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Inventor： Hideo Konno ,  Junichi Taniuchi ,  Ryosuke Harada ,  Toshiyuki Shigetomi ,  Yasushi Masahiro

IPC: C07C49/92 ,  C07F15/00

CPC classification number: C07F15/0033 ,  C07C49/92 ,  C07F15/004

Abstract: The present invention relates to a raw material for a cyclometalated iridium complex, and provides a technique that makes it possible to obtain a cyclometalated iridium complex in higher yield at a lower reaction temperature than using tris(2,4-pentanedionato)iridium(III). The present invention relates to a raw material for a cyclometalated iridium complex, including an organic iridium material for producing a cyclometalated iridium complex, the organic iridium material being a tris(β-diketonato)iridium(III), in which an asymmetric β-diketone is coordinated to iridium.

公开(公告)号：US09108997B2

公开(公告)日：2015-08-18

申请号：US14396861

申请日：2013-06-06

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Shunichi Nabeya ,  Toshiyuki Shigetomi ,  Masayuki Saito

IPC: C07F17/02 ,  C07F15/00 ,  B01J23/44 ,  C07C45/79 ,  C07C45/85 ,  B01J23/42 ,  B01J23/46 ,  B01J25/02

CPC classification number: C07F15/0046 ,  B01J23/42 ,  B01J23/44 ,  B01J23/462 ,  B01J25/02 ,  C07C45/79 ,  C07C45/85 ,  C07C49/92

Abstract: The present invention is a method for recycling an organic ruthenium compound for chemical vapor deposition, wherein an unreacted organic ruthenium compound is extracted from a used raw material through a thin film formation process. The method includes the following steps (a) to (c). (a) A modification step in which the used raw material and a hydrogenation catalyst are brought into contact with each other in a hydrogen atmosphere, thereby hydrogenating an oxidized organic ruthenium compound in the used raw material. (b) An adsorption step in which the used raw material and an adsorbent are brought into contact with each other, thereby removing impurities in the used raw material. (c) A restoration step in which the used raw material is heated at a temperature that is not lower than −100° C. and not higher than −10° C. with respect to the decomposition temperature of the organic ruthenium compound for eight hours or more, thereby adjusting the ratio of the isomers of the organic ruthenium compound in the used raw material.

Abstract translation: 本发明是一种用于化学气相沉积的有机钌化合物的再循环方法，其中通过薄膜形成方法从使用的原料中提取未反应的有机钌化合物。 该方法包括以下步骤（a）至（c）。 （a）在氢气氛中使使用的原料和氢化催化剂彼此接触的改性步骤，从而使所使用的原料中的氧化的有机钌化合物氢化。 （b）使原料和吸附剂相互接触的吸附工序，除去原料中的杂质。 （c）将有机钌化合物的分解温度在不低于-100℃且不高于-10℃的温度下加热8小时的恢复步骤 以上，由此调整所使用的原料中的有机钌化合物的异构体的比例。

公开(公告)号：US11434563B2

公开(公告)日：2022-09-06

申请号：US17299294

申请日：2019-12-02

Applicant: TANAKA KIKINZOKU KOGYO K.K.

Inventor： Ryosuke Harada ,  Teruhisa Iwai ,  Toshiyuki Shigetomi ,  Shigeyuki Ootake ,  Seung-Joon Lee

IPC: C23C16/18

Abstract: The present invention relates to a raw material for chemical deposition for producing a ruthenium thin film or a ruthenium compound thin film by a chemical deposition method, containing a ruthenium complex represented by the following Chemical Formula 1. In Chemical Formula 1, ligands L1 and L2 coordinated to ruthenium are represented by the following Chemical Formula 2. The raw material for chemical deposition according to the present invention can be formed into a high quality thin film even if a reaction gas containing an oxygen atom is not used. wherein R1 to R12, which are substituents of the ligands L1 and L2, are each independently any one of a hydrogen atom, and a linear or branched alkyl group having a carbon number of 1 or more and 4 or less.