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WO2006012052A2 - Precurseurs utilises pour le depot chimique en phase vapeur contenant des ligands amidinates - Google Patents

Precurseurs utilises pour le depot chimique en phase vapeur contenant des ligands amidinates Download PDF

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Publication number
WO2006012052A2
WO2006012052A2 PCT/US2005/021439 US2005021439W WO2006012052A2 WO 2006012052 A2 WO2006012052 A2 WO 2006012052A2 US 2005021439 W US2005021439 W US 2005021439W WO 2006012052 A2 WO2006012052 A2 WO 2006012052A2
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WO
WIPO (PCT)
Prior art keywords
methylphenyl
phenyl
metalloamidinate
amidinate
different
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.)
Ceased
Application number
PCT/US2005/021439
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English (en)
Other versions
WO2006012052A3 (fr
Inventor
Michael B. Abrams
Mark A. Aubart
David A. Russo
Linda B. Bruce-Gerz
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.)
Arkema Inc
Original Assignee
Arkema Inc
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 Arkema Inc filed Critical Arkema Inc
Publication of WO2006012052A2 publication Critical patent/WO2006012052A2/fr
Publication of WO2006012052A3 publication Critical patent/WO2006012052A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/16—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage

Definitions

  • the present invention is directed to novel precursors for use in chemical vapor deposition. More particularly, the present invention is directed to amidinate ligand containing precursors such as metalloamidinates as chemical vapor deposition precursors.
  • APCVD atmospheric pressure chemical vapor deposition
  • very few species have the combination of volatility (traditionally obtained through construction of low molecular-weight, fluorine-incorporating molecules) and stability (clean decomposition to M, M x O y , M x N y at temperatures above those required for volatility).
  • suitable precursors for chemical vapor deposition such as atmospheric pressure chemical vapor deposition (APCVD) of films of metals, metal oxides, and metal nitrides, in which the physical properties of the precursors (or films) may be controlled by modification of the precursor ligand array.
  • the amidinate [R 1 NC(R 2 )NR 3 ] " ligands are low molecular- weight species, capable of multiple binding modes (monodentate (Ia), chelating (Ib 3 Ic), bridging (Id, Ie)) that may support a variety of metal fragments and metal oxidation states.
  • substitution patterns (R 1 , R 2 , R 3 ) on the amidinate ligand are accessible from starting materials. This permits systematic modification of steric and electronic effects, as well as incorporation of fluorinated substituents, which has been demonstrated to impart volatility to precursors such as (hexafluoroacetylacetonate)Cu(vinyltrimethylsilane) for Cu- deposition.
  • precursor stability and deposition characteristics are dependent on the geometry as well as on the steric and electronic influences imparted by specific R 1"3 , M, and L n .
  • Experimental and computational evaluation of the relationships between these factors is necessary for development and optimization of suitable precursors for chemical vapor deposition of metal-, metal-oxide-, and metal-nitride films.
  • a 1 H COSY spectrum reveals the existence of at least 4 products from 2e/NiCl 2 ; the 1 H NMR spectrum of the major product (-50% of the iPr resonances) is consistent with the bis(amidinate) ⁇ (iPr)NC[2,6-(CH 3 ) 2 -Ph]C(iPr) ⁇ 2 Ni(THF) x (5).
  • Also novel to this invention is the synthesis of mixed (amidinate) 1 (amidinate) 2 M complexes such as 7.
  • the ability to combine different amidinate ligands onto the same metal center may allow additional fine tuning of molecular and macroscopic properties over those dictated by (amidinate) 2 M species.
  • This also provides proof-of-concept for the generation of mixed ligand complexes such as (for example) (amidinate)M(alkyl), (amidinate)M(alkoxide), and (amidinate)M( ⁇ -diketonate) .
  • This present invention demonstrates that novel amidinate ligands containing both symmetric- and unsymmetric N- substitution are accessible from readily available starting materials, and that a wide variety of substituents may be successfully be incorporated into the amidinate framework.
  • amidinate (amidinate) (amidinate) M complexes such as 7.
  • the ability to combine different amidinate ligands onto the same metal center allows additional "fine tuning" of molecular and macroscopic properties over those dictated by (amidinate) 2 M species.
  • the preferred principle and method of operation may be extended in several ways without losing the advantages of the invention.
  • the invention may be extended to metalloamidinates with amidinate substiruents not listed explicitly above, but that would be obvious to those skilled in the art.
  • the amidinate ligands may be coordinated to metals other than Cu and Ni; this invention covers metalloamidinates of main-group- and transition metals for use as CVD precursors, including but not limited to nickel, copper, zinc, titanium, silver, molybdenum, tungsten, tantalum, tin, aluminum, gallium, and indium.
  • This invention also includes metalloamidinate precursors in which one- or more than two amidinate fragments are bound to a metal center.
  • the amidinates may have the same or different substituents.
  • the metal fragment to which one or more amidinate ligand is bound may have additional coordinated (ancillary) ligands; these ligands may include alkyls, aryls, hydrides, alkoxides, acetylacetonates and other ⁇ -diketonates, amines, phosphines, alkenes, alkynes, allyls, cyclopentadienyls, carbonyls, nitriles, halides, oxides, imides, nitrides, and tetrahydrofurans.
  • Amidinate-ancillary ligand interactions may also be used to influence precursor properties
  • This invention also covers metalloamidinates made by methods other than addition of lithium- or magnesium-amidinates to metal halides.
  • This invention covers the use of metalloamidinates as precursors for the deposition of metal-, metal-oxide-, and metal-nitride films of main-group- or transition-metals. Techniques used to deposit these films include, but are not limited to pyrolytic atmospheric pressure CVD, low-pressure CVD, plasma assisted CVD, solution spray CVD, and powder spray CVD.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Vapour Deposition (AREA)

Abstract

La présente invention concerne des précurseurs destinés à être utilisés dans le dépôt chimique en phase vapeur contenant des ligands amidinates. Plus particulièrement, la présente invention concerne des précurseurs contenant des ligands amidinates tels que des métalloamidinates en tant que précurseurs utilisés pour le dépôt chimique en phase vapeur. L'invention concerne également des précurseurs appropriés pour le dépôt chimique en phase vapeur tel que le dépôt chimique en phase vapeur à la pression atmosphérique (APCVD) de films de métaux, d'oxydes métalliques et de nitrures métalliques, dans lequel les propriétés physiques des précurseurs (ou films) peuvent être contrôlées par modification du réseau de ligands du précurseur.
PCT/US2005/021439 2004-06-25 2005-06-17 Precurseurs utilises pour le depot chimique en phase vapeur contenant des ligands amidinates Ceased WO2006012052A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58294404P 2004-06-25 2004-06-25
US60/582,944 2004-06-25

Publications (2)

Publication Number Publication Date
WO2006012052A2 true WO2006012052A2 (fr) 2006-02-02
WO2006012052A3 WO2006012052A3 (fr) 2006-04-20

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Country Link
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Cited By (35)

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JP2006328034A (ja) * 2005-05-30 2006-12-07 Nippon Zeon Co Ltd 遷移金属錯体、環状オレフィン重合用触媒、および環状オレフィン重合体の製造方法
JP2008502680A (ja) * 2004-06-16 2008-01-31 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド 銅薄膜の堆積前駆体として有用な銅（ｉ）化合物
US7547631B2 (en) 2006-07-31 2009-06-16 Rohm And Haas Electronic Materials Llc Organometallic compounds
FR2929449A1 (fr) * 2008-03-28 2009-10-02 Stmicroelectronics Tours Sas S Procede de formation d'une couche d'amorcage de depot d'un metal sur un substrat
WO2009149372A1 (fr) * 2008-06-05 2009-12-10 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Préparation de précurseurs contenant du lanthanide et dépôt de films contenant du lanthanide
JP2010514918A (ja) * 2006-11-02 2010-05-06 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド 金属薄膜のｃｖｄ／ａｌｄに有用なアンチモンおよびゲルマニウム錯体
WO2010079979A3 (fr) * 2009-01-08 2010-12-02 Techno Semichem, Co., Ltd. Nouveaux complexes de germanium avec un ligand dérivé d'amidine et leur procédé de préparation
WO2011033903A1 (fr) * 2009-09-15 2011-03-24 東京エレクトロン株式会社 Procédé de formation de film de siliciure métallique
US8093140B2 (en) 2007-10-31 2012-01-10 Advanced Technology Materials, Inc. Amorphous Ge/Te deposition process
EP2439208A1 (fr) * 2007-07-20 2012-04-11 Rohm and Haas Company Procédé de préparation des composés organométalliques
US8163341B2 (en) 2008-11-19 2012-04-24 Micron Technology, Inc. Methods of forming metal-containing structures, and methods of forming germanium-containing structures
US8168811B2 (en) 2008-07-22 2012-05-01 Advanced Technology Materials, Inc. Precursors for CVD/ALD of metal-containing films
US8288198B2 (en) 2006-05-12 2012-10-16 Advanced Technology Materials, Inc. Low temperature deposition of phase change memory materials
US8330136B2 (en) 2008-12-05 2012-12-11 Advanced Technology Materials, Inc. High concentration nitrogen-containing germanium telluride based memory devices and processes of making
US8455049B2 (en) 2007-08-08 2013-06-04 Advanced Technology Materials, Inc. Strontium precursor for use in chemical vapor deposition, atomic layer deposition and rapid vapor deposition
US8524931B2 (en) 2007-01-17 2013-09-03 Advanced Technology Materials, Inc. Precursor compositions for ALD/CVD of group II ruthenate thin films
KR101304760B1 (ko) * 2010-04-07 2013-09-05 레르 리키드 쏘시에떼 아노님 뿌르 레？드 에렉스뿔라따시옹 데 프로세데 조르즈 클로드 증착용 티타늄 함유 전구체
US8617972B2 (en) 2009-05-22 2013-12-31 Advanced Technology Materials, Inc. Low temperature GST process
US8674127B2 (en) 2008-05-02 2014-03-18 Advanced Technology Materials, Inc. Antimony compounds useful for deposition of antimony-containing materials
US8796068B2 (en) 2008-02-24 2014-08-05 Advanced Technology Materials, Inc. Tellurium compounds useful for deposition of tellurium containing materials
US8809849B2 (en) 2008-06-05 2014-08-19 American Air Liquide, Inc. Preparation of cerium-containing precursors and deposition of cerium-containing films
US8834968B2 (en) 2007-10-11 2014-09-16 Samsung Electronics Co., Ltd. Method of forming phase change material layer using Ge(II) source, and method of fabricating phase change memory device
US8852686B2 (en) 2007-10-11 2014-10-07 Samsung Electronics Co., Ltd. Method of forming phase change material layer using Ge(II) source, and method of fabricating phase change memory device
US9012876B2 (en) 2010-03-26 2015-04-21 Entegris, Inc. Germanium antimony telluride materials and devices incorporating same
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US9099301B1 (en) 2013-12-18 2015-08-04 L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Preparation of lanthanum-containing precursors and deposition of lanthanum-containing films
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Cited By (62)

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JP2008502680A (ja) * 2004-06-16 2008-01-31 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド 銅薄膜の堆積前駆体として有用な銅（ｉ）化合物
JP2006328034A (ja) * 2005-05-30 2006-12-07 Nippon Zeon Co Ltd 遷移金属錯体、環状オレフィン重合用触媒、および環状オレフィン重合体の製造方法
US9534285B2 (en) 2006-03-10 2017-01-03 Entegris, Inc. Precursor compositions for atomic layer deposition and chemical vapor deposition of titanate, lanthanate, and tantalate dielectric films
US8679894B2 (en) 2006-05-12 2014-03-25 Advanced Technology Materials, Inc. Low temperature deposition of phase change memory materials
US8288198B2 (en) 2006-05-12 2012-10-16 Advanced Technology Materials, Inc. Low temperature deposition of phase change memory materials
US7547631B2 (en) 2006-07-31 2009-06-16 Rohm And Haas Electronic Materials Llc Organometallic compounds
EP2511280A1 (fr) * 2006-11-02 2012-10-17 Advanced Technology Materials, Inc. Complexes amidinate de germanium utiles pour CVD/ALD de films minces métalliques
US8268665B2 (en) 2006-11-02 2012-09-18 Advanced Technology Materials, Inc. Antimony and germanium complexes useful for CVD/ALD of metal thin films
US9219232B2 (en) 2006-11-02 2015-12-22 Entegris, Inc. Antimony and germanium complexes useful for CVD/ALD of metal thin films
JP2010514918A (ja) * 2006-11-02 2010-05-06 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド 金属薄膜のｃｖｄ／ａｌｄに有用なアンチモンおよびゲルマニウム錯体
US8008117B2 (en) 2006-11-02 2011-08-30 Advanced Technology Materials, Inc. Antimony and germanium complexes useful for CVD/ALD of metal thin films
JP2013144851A (ja) * 2006-11-02 2013-07-25 Advanced Technology Materials Inc 金属薄膜のｃｖｄ／ａｌｄに有用なアンチモンおよびゲルマニウム錯体
US8709863B2 (en) 2006-11-02 2014-04-29 Advanced Technology Materials, Inc. Antimony and germanium complexes useful for CVD/ALD of metal thin films
EP2078102A4 (fr) * 2006-11-02 2010-11-24 Advanced Tech Materials Complexes d'antimoine et de germanium utiles pour les cvd/ald des films métalliques minces
US8524931B2 (en) 2007-01-17 2013-09-03 Advanced Technology Materials, Inc. Precursor compositions for ALD/CVD of group II ruthenate thin films
EP2439208A1 (fr) * 2007-07-20 2012-04-11 Rohm and Haas Company Procédé de préparation des composés organométalliques
US8455049B2 (en) 2007-08-08 2013-06-04 Advanced Technology Materials, Inc. Strontium precursor for use in chemical vapor deposition, atomic layer deposition and rapid vapor deposition
US8852686B2 (en) 2007-10-11 2014-10-07 Samsung Electronics Co., Ltd. Method of forming phase change material layer using Ge(II) source, and method of fabricating phase change memory device
US8834968B2 (en) 2007-10-11 2014-09-16 Samsung Electronics Co., Ltd. Method of forming phase change material layer using Ge(II) source, and method of fabricating phase change memory device
US8093140B2 (en) 2007-10-31 2012-01-10 Advanced Technology Materials, Inc. Amorphous Ge/Te deposition process
US8796068B2 (en) 2008-02-24 2014-08-05 Advanced Technology Materials, Inc. Tellurium compounds useful for deposition of tellurium containing materials
US9537095B2 (en) 2008-02-24 2017-01-03 Entegris, Inc. Tellurium compounds useful for deposition of tellurium containing materials
FR2929449A1 (fr) * 2008-03-28 2009-10-02 Stmicroelectronics Tours Sas S Procede de formation d'une couche d'amorcage de depot d'un metal sur un substrat
WO2009125143A3 (fr) * 2008-03-28 2009-12-10 Stmicroelectronics (Tours) Sas Procede de formation d'une couche d'amorcage de depot d'un metal sur un substrat
US9093381B2 (en) 2008-03-28 2015-07-28 Stmicroelectronics (Tours) Sas Method for forming a seed layer for the deposition of a metal on a substrate
US9034688B2 (en) 2008-05-02 2015-05-19 Entegris, Inc. Antimony compounds useful for deposition of antimony-containing materials
US8674127B2 (en) 2008-05-02 2014-03-18 Advanced Technology Materials, Inc. Antimony compounds useful for deposition of antimony-containing materials
US8283201B2 (en) 2008-06-05 2012-10-09 American Air Liquide, Inc. Preparation of lanthanide-containing precursors and deposition of lanthanide-containing films
US9711347B2 (en) 2008-06-05 2017-07-18 American Air Liquide, Inc. Preparation of lanthanide-containing precursors and deposition of lanthanide-containing films
US9384963B2 (en) 2008-06-05 2016-07-05 American Air Liquide, Inc. Preparation of cerium-containing precursor and deposition of cerium-containing films
US8507905B2 (en) 2008-06-05 2013-08-13 American Air Liquide, Inc. Preparation of lanthanide-containing precursors and deposition of lanthanide-containing films
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WO2009149372A1 (fr) * 2008-06-05 2009-12-10 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Préparation de précurseurs contenant du lanthanide et dépôt de films contenant du lanthanide
US8809849B2 (en) 2008-06-05 2014-08-19 American Air Liquide, Inc. Preparation of cerium-containing precursors and deposition of cerium-containing films
US8168811B2 (en) 2008-07-22 2012-05-01 Advanced Technology Materials, Inc. Precursors for CVD/ALD of metal-containing films
US8323736B2 (en) 2008-11-19 2012-12-04 Micron Technology, Inc. Methods of forming metal-containing structures, and methods of forming germanium-containing structures
US8163341B2 (en) 2008-11-19 2012-04-24 Micron Technology, Inc. Methods of forming metal-containing structures, and methods of forming germanium-containing structures
US8330136B2 (en) 2008-12-05 2012-12-11 Advanced Technology Materials, Inc. High concentration nitrogen-containing germanium telluride based memory devices and processes of making
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JP2012514635A (ja) * 2009-01-08 2012-06-28 テクノ セミケム シーオー．， エルティーディー． アミジン誘導体をリガンドとする新規ゲルマニウム化合物及びその製造方法
US9070875B2 (en) 2009-05-22 2015-06-30 Entegris, Inc. Low temperature GST process
US8617972B2 (en) 2009-05-22 2013-12-31 Advanced Technology Materials, Inc. Low temperature GST process
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WO2011033903A1 (fr) * 2009-09-15 2011-03-24 東京エレクトロン株式会社 Procédé de formation de film de siliciure métallique
JP2011066060A (ja) * 2009-09-15 2011-03-31 Tokyo Electron Ltd 金属シリサイド膜の形成方法
CN102365715A (zh) * 2009-09-15 2012-02-29 东京毅力科创株式会社 金属硅化物膜的形成方法
US9012876B2 (en) 2010-03-26 2015-04-21 Entegris, Inc. Germanium antimony telluride materials and devices incorporating same
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