WO2003095701A8 - Volatile copper(ii) complexes for deposition of copper films by atomic layer deposition - Google Patents

Volatile copper(ii) complexes for deposition of copper films by atomic layer deposition

Info

Publication number
WO2003095701A8
WO2003095701A8 PCT/US2003/001846 US0301846W WO03095701A8 WO 2003095701 A8 WO2003095701 A8 WO 2003095701A8 US 0301846 W US0301846 W US 0301846W WO 03095701 A8 WO03095701 A8 WO 03095701A8
Authority
WO
WIPO (PCT)
Prior art keywords
copper
deposition
complexes
atomic layer
volatile
Prior art date
Application number
PCT/US2003/001846
Other languages
French (fr)
Other versions
WO2003095701A1 (en
Inventor
Alexander Zak Bradley
David Lincoln Thorn
Jeffery Scott Thompson
Original Assignee
Du Pont
Alexander Zak Bradley
David Lincoln Thorn
Jeffery Scott Thompson
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
Priority to JP2004503688A priority Critical patent/JP2005520053A/en
Priority to KR10-2004-7011062A priority patent/KR20040077733A/en
Application filed by Du Pont, Alexander Zak Bradley, David Lincoln Thorn, Jeffery Scott Thompson filed Critical Du Pont
Priority to EP20030750016 priority patent/EP1466032A1/en
Priority to US10/499,934 priority patent/US20050003075A1/en
Publication of WO2003095701A1 publication Critical patent/WO2003095701A1/en
Publication of WO2003095701A8 publication Critical patent/WO2003095701A8/en

Links

Classifications

    • 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
    • C23C16/44—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 method of coating
    • C23C16/455—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 method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
    • C23C16/45523—Pulsed gas flow or change of composition over time
    • C23C16/45525—Atomic layer deposition [ALD]
    • C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD
    • 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
    • C07C251/10—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 an unsaturated carbon skeleton
    • C07C251/12—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 an unsaturated carbon skeleton being acyclic
    • 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
    • C07C251/10—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 an unsaturated carbon skeleton
    • C07C251/16—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 an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • 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
    • C23C16/44—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 method of coating
    • C23C16/455—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 method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
    • C23C16/45523—Pulsed gas flow or change of composition over time
    • C23C16/45525—Atomic layer deposition [ALD]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/28—Manufacture of electrodes on semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/268
    • H01L21/283—Deposition of conductive or insulating materials for electrodes conducting electric current
    • H01L21/288—Deposition of conductive or insulating materials for electrodes conducting electric current from a liquid, e.g. electrolytic deposition
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
    • H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
    • H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
    • H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
    • H01L21/0228—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition deposition by cyclic CVD, e.g. ALD, ALE, pulsed CVD
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/314—Inorganic layers
    • H01L21/3141—Deposition using atomic layer deposition techniques [ALD]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]

Abstract

The present invention relates to novel 1,3-diimine copper complexes and the use of 1,3-diimine copper complexes for the deposition of copper on substrates or in or on porous solids in an Atomic Layer Deposition process. This invention also provides a process for making amino-imines and novel amino-imines.
PCT/US2003/001846 2002-01-18 2003-01-21 Volatile copper(ii) complexes for deposition of copper films by atomic layer deposition WO2003095701A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2004503688A JP2005520053A (en) 2002-01-18 2003-01-17 Volatile copper (II) complexes for depositing copper thin films by atomic layer deposition
KR10-2004-7011062A KR20040077733A (en) 2002-01-18 2003-01-17 Volatile copper(ii) complexes for deposition of copper films by atomic layer deposition
EP20030750016 EP1466032A1 (en) 2002-01-18 2003-01-21 Volatile copper(ii) complexes for deposition of copper films by atomic layer deposition
US10/499,934 US20050003075A1 (en) 2002-01-18 2003-01-21 Volatile copper(II) complexes for deposition of copper films by atomic layer deposition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US34963902P 2002-01-18 2002-01-18
US60/349,639 2002-01-18

Publications (2)

Publication Number Publication Date
WO2003095701A1 WO2003095701A1 (en) 2003-11-20
WO2003095701A8 true WO2003095701A8 (en) 2004-05-21

Family

ID=29420294

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/001846 WO2003095701A1 (en) 2002-01-18 2003-01-21 Volatile copper(ii) complexes for deposition of copper films by atomic layer deposition

Country Status (7)

Country Link
US (6) US6939578B2 (en)
EP (1) EP1466032A1 (en)
JP (1) JP2005520053A (en)
KR (1) KR20040077733A (en)
CN (1) CN100360709C (en)
AU (1) AU2003210599A1 (en)
WO (1) WO2003095701A1 (en)

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US7049226B2 (en) * 2001-09-26 2006-05-23 Applied Materials, Inc. Integration of ALD tantalum nitride for copper metallization
US7199255B2 (en) * 2001-12-18 2007-04-03 Univation Technologies, Llc Imino-amide catalysts for olefin polymerization
JP2005520053A (en) * 2002-01-18 2005-07-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Volatile copper (II) complexes for depositing copper thin films by atomic layer deposition
US6911391B2 (en) * 2002-01-26 2005-06-28 Applied Materials, Inc. Integration of titanium and titanium nitride layers
US20040009665A1 (en) * 2002-06-04 2004-01-15 Applied Materials, Inc. Deposition of copper films
US20040247905A1 (en) * 2003-04-16 2004-12-09 Bradley Alexander Zak Volatile copper(I) complexes for deposition of copper films by atomic layer deposition
US20050227007A1 (en) * 2004-04-08 2005-10-13 Bradley Alexander Z Volatile copper(I) complexes for deposition of copper films by atomic layer deposition
WO2006015225A1 (en) * 2004-07-30 2006-02-09 E.I. Dupont De Nemours And Company Copper (ii) complexes for deposition of copper films by atomic layer deposition
US7604840B2 (en) * 2004-08-16 2009-10-20 E. I. Du Pont De Nemours And Company Atomic layer deposition of copper using surface-activation agents
EP1629902A1 (en) * 2004-08-30 2006-03-01 E.I. Dupont De Nemours And Company Method of copper deposition from a supercritical fluid solution containing copper (1) complexes with a neutral ligand
US7416994B2 (en) * 2005-06-28 2008-08-26 Micron Technology, Inc. Atomic layer deposition systems and methods including metal beta-diketiminate compounds
US7572731B2 (en) * 2005-06-28 2009-08-11 Micron Technology, Inc. Unsymmetrical ligand sources, reduced symmetry metal-containing compounds, and systems and methods including same
US7439338B2 (en) 2005-06-28 2008-10-21 Micron Technology, Inc. Beta-diketiminate ligand sources and metal-containing compounds thereof, and systems and methods including same
US7776394B2 (en) * 2005-08-08 2010-08-17 E.I. Du Pont De Nemours And Company Atomic layer deposition of metal-containing films using surface-activating agents
US7632351B2 (en) * 2005-08-08 2009-12-15 E. I. Du Pont De Nemours And Company Atomic layer deposition processes for the formation of ruthenium films, and ruthenium precursors useful in such processes
US20070191638A1 (en) * 2006-02-10 2007-08-16 Park Kyung-Ho Processes for the synthesis of N,N'-substituted 1,3-diketimines
WO2008018861A1 (en) * 2006-08-07 2008-02-14 E. I. Du Pont De Nemours And Company Copper(i) complexes and processes for deposition of copper films by atomic layer deposition
US7488435B2 (en) 2006-08-07 2009-02-10 E. I. Du Pont De Nemours And Company Copper(I) complexes and processes for deposition of copper films by atomic layer deposition
US7582757B2 (en) 2006-09-06 2009-09-01 E. I. Du Pont De Nemours And Company Electroluminescent complexes of Ir(III) and devices
US7692222B2 (en) * 2006-11-07 2010-04-06 Raytheon Company Atomic layer deposition in the formation of gate structures for III-V semiconductor
US20090130466A1 (en) * 2007-11-16 2009-05-21 Air Products And Chemicals, Inc. Deposition Of Metal Films On Diffusion Layers By Atomic Layer Deposition And Organometallic Precursor Complexes Therefor
JP5854839B2 (en) * 2008-11-11 2016-02-09 ユニバーサル ディスプレイ コーポレイション Phosphorescent emitter
US8076243B2 (en) * 2009-01-26 2011-12-13 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Metal precursors for deposition of metal-containing films
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US8692010B1 (en) 2012-07-13 2014-04-08 American Air Liquide, Inc. Synthesis method for copper compounds
KR101644676B1 (en) * 2013-06-20 2016-08-01 주식회사 엘지화학 Metal particles of core-shell structure and method for manufacturing the same
JP6775531B2 (en) * 2015-06-11 2020-10-28 ナショナル リサーチ カウンシル オブ カナダ Preparation of highly conductive copper film
TW201842088A (en) 2017-02-08 2018-12-01 加拿大國家研究委員會 Printable molecular ink
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US20040247905A1 (en) * 2003-04-16 2004-12-09 Bradley Alexander Zak Volatile copper(I) complexes for deposition of copper films by atomic layer deposition

Also Published As

Publication number Publication date
CN100360709C (en) 2008-01-09
US7268365B2 (en) 2007-09-11
CN1617948A (en) 2005-05-18
US6939578B2 (en) 2005-09-06
US20050107283A1 (en) 2005-05-19
WO2003095701A1 (en) 2003-11-20
US7186835B2 (en) 2007-03-06
US20050267305A1 (en) 2005-12-01
US20030232142A1 (en) 2003-12-18
JP2005520053A (en) 2005-07-07
US7388113B2 (en) 2008-06-17
US20050158479A1 (en) 2005-07-21
AU2003210599A1 (en) 2003-11-11
US20050003075A1 (en) 2005-01-06
KR20040077733A (en) 2004-09-06
EP1466032A1 (en) 2004-10-13
US20060237718A1 (en) 2006-10-26
US7087774B2 (en) 2006-08-08

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