US20120251724A1 - Beta-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same - Google Patents

Beta-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same Download PDF

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Publication number
US20120251724A1
US20120251724A1 US13/435,760 US201213435760A US2012251724A1 US 20120251724 A1 US20120251724 A1 US 20120251724A1 US 201213435760 A US201213435760 A US 201213435760A US 2012251724 A1 US2012251724 A1 US 2012251724A1
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US
United States
Prior art keywords
metal
compound
group
ketoimine
complex compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/435,760
Other languages
English (en)
Inventor
Youn-Joung Cho
Senji Wada
Jung-Sik Choi
Jin-Seo Lee
Atsushi Sakurai
Kyoo-chul Cho
Atsuya Yoshinaka
Haruyoshi Sato
Junji UEYAMA.
Tomoharu YOSHINO
Masako Shimizu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adeka Corp
Samsung Electronics Co Ltd
Original Assignee
Adeka Corp
Samsung Electronics Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adeka Corp, Samsung Electronics Co Ltd filed Critical Adeka Corp
Assigned to SAMSUNG ELECTRONICS CO., LTD., ADEKA CORPORATION reassignment SAMSUNG ELECTRONICS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHO, KYOO-CHUL, CHO, YOUN-JOUNG, CHOI, JUNG-SIK, LEE, JIN-SEO, SAKURAI, ATSUSHI, SATO, HARUYOSHI, SHIMIZU, MASAKO, UEYAMA, JUNJI, WADA, SENJI, YOSHINAKA, ATSUYA, YOSHINO, TOMOHARU
Publication of US20120251724A1 publication Critical patent/US20120251724A1/en
Priority to US14/317,102 priority Critical patent/US9359382B2/en
Priority to US14/319,554 priority patent/US9359383B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/06—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material
    • C23C16/18—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material from metallo-organic compounds

Definitions

  • R 1 and R 2 are each independently a C 1 -C 5 alkyl group
  • M represents a metal
  • n is an integer ranging from 1 to 5.
  • FIG. 2 illustrates the 1 H-NMR spectrum of the ⁇ -ligand prepared in Synthesis Example 2
  • an alkylating agent is added to a hydroxypivalic acid ester to synthesize an intermediate ether ester compound.
  • the metal complex compound according to an embodiment may be represented by the following Formula 3:
  • the thin film forming method includes supplying a metal precursor including the metal complex compound above described, and forming a thin film on a workpiece by vaporizing the supplied metal precursor.
  • the second raw material may contain a reactive gas to react with the first metal precursor.
  • the reactive gas may be, for example, hydrogen (H 2 ), ammonia (NH 3 ), hydrazine (NH 2 NH 2 ), or silane.
  • steam (H 2 O), oxygen (O 2 ), hydrogen peroxide (H 2 O 2 ) or ozone (O 3 ) may be used as the reactive gas to deposit a metal oxide thin film.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Chemical Vapour Deposition (AREA)
US13/435,760 2011-04-01 2012-03-30 Beta-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same Abandoned US20120251724A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US14/317,102 US9359382B2 (en) 2011-04-01 2014-06-27 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same
US14/319,554 US9359383B2 (en) 2011-04-01 2014-06-30 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2011-0030224 2011-04-01
KR1020110030224A KR101711095B1 (ko) 2011-04-01 2011-04-01 β-케토이민 리간드, 이의 제조 방법, 이를 포함하는 금속 착화합물 및 이를 이용한 박막 형성 방법

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US14/317,102 Division US9359382B2 (en) 2011-04-01 2014-06-27 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same
US14/319,554 Division US9359383B2 (en) 2011-04-01 2014-06-30 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same

Publications (1)

Publication Number Publication Date
US20120251724A1 true US20120251724A1 (en) 2012-10-04

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Application Number Title Priority Date Filing Date
US13/435,760 Abandoned US20120251724A1 (en) 2011-04-01 2012-03-30 Beta-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same
US14/317,102 Active 2032-05-19 US9359382B2 (en) 2011-04-01 2014-06-27 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same
US14/319,554 Active 2032-05-26 US9359383B2 (en) 2011-04-01 2014-06-30 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same

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Application Number Title Priority Date Filing Date
US14/317,102 Active 2032-05-19 US9359382B2 (en) 2011-04-01 2014-06-27 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same
US14/319,554 Active 2032-05-26 US9359383B2 (en) 2011-04-01 2014-06-30 β-ketoimine ligand, method of preparing the same, metal complex comprising the same and method of forming thin film using the same

Country Status (2)

Country Link
US (3) US20120251724A1 (ko)
KR (1) KR101711095B1 (ko)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070248754A1 (en) * 2006-04-25 2007-10-25 Xinjian Lei Metal Complexes of Polydentate Beta-Ketoiminates

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950790A (en) 1988-11-14 1990-08-21 Air Products And Chemicals, Inc. Volatile fluorinated β-ketoimines and associated metal complexes
US6099903A (en) 1999-05-19 2000-08-08 Research Foundation Of State University Of New York MOCVD processes using precursors based on organometalloid ligands
US20100119726A1 (en) 2008-11-07 2010-05-13 Air Products And Chemicals, Inc. Group 2 Metal Precursors For Deposition Of Group 2 Metal Oxide Films
JP5544198B2 (ja) * 2010-03-17 2014-07-09 株式会社Ａｄｅｋａ β−ケトイミン化合物、金属錯体及び薄膜形成用原料

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070248754A1 (en) * 2006-04-25 2007-10-25 Xinjian Lei Metal Complexes of Polydentate Beta-Ketoiminates

Also Published As

Publication number Publication date
US20140316164A1 (en) 2014-10-23
US20140309456A1 (en) 2014-10-16
US9359382B2 (en) 2016-06-07
KR101711095B1 (ko) 2017-03-02
KR20120111627A (ko) 2012-10-10
US9359383B2 (en) 2016-06-07

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Date Code Title Description
AS Assignment

Owner name: ADEKA CORPORATION, JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHO, YOUN-JOUNG;WADA, SENJI;CHOI, JUNG-SIK;AND OTHERS;SIGNING DATES FROM 20120308 TO 20120319;REEL/FRAME:027965/0183

Owner name: SAMSUNG ELECTRONICS CO., LTD., KOREA, REPUBLIC OF

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHO, YOUN-JOUNG;WADA, SENJI;CHOI, JUNG-SIK;AND OTHERS;SIGNING DATES FROM 20120308 TO 20120319;REEL/FRAME:027965/0183

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION