US20080299322A1 - Copper (I) Complexes for Deposition of Copper Films by Atomic Layer Deposition - Google Patents

Copper (I) Complexes for Deposition of Copper Films by Atomic Layer Deposition Download PDF

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US20080299322A1
US20080299322A1 US11/658,368 US65836805A US2008299322A1 US 20080299322 A1 US20080299322 A1 US 20080299322A1 US 65836805 A US65836805 A US 65836805A US 2008299322 A1 US2008299322 A1 US 2008299322A1
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copper
independently selected
substrate
hydrogen
alkyl
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Bradley Alexander Zak
Jeffery Scott Thompson
Kyung-ho Park
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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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 potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table 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
    • H01L21/285—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation
    • H01L21/28506—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers
    • H01L21/28512—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers on semiconductor bodies comprising elements of Group IV of the Periodic Table
    • H01L21/28556—Deposition of conductive or insulating materials for electrodes conducting electric current from a gas or vapour, e.g. condensation of conductive layers on semiconductor bodies comprising elements of Group IV of the Periodic Table by chemical means, e.g. CVD, LPCVD, PECVD, laser CVD
    • H01L21/28562—Selective deposition

Definitions

  • the present invention relates to novel 1,3-diimine copper complexes.
  • the invention also relates to processes for forming copper deposits on substrates or in or on porous solids, using the 1,3-diimine copper complexes.
  • Atomic layer deposition (ALD) processes are useful for the creation of thin films, as described by M. Ritala and M. Leskela in “Atomic Layer Deposition” in Handbook of Thin Film Materials, H. S. Nalwa, Editor, Academic Press, San Diego, 2001, Volume 1, Chapter 2. Such films, especially metal and metal oxide films, are critical components in the manufacture of electronic circuits and devices.
  • a copper precursor and a reducing agent are alternatively introduced into a reaction chamber. After the copper precursor is introduced into the reaction chamber and allowed to adsorb onto a substrate, the excess (unadsorbed) precursor vapor is pumped or purged from the chamber. This process is followed by introduction of a reducing agent that reacts with the copper precursor on the substrate surface to form copper metal and a free form of the ligand. This cycle can be repeated if needed to achieve the desired film thickness.
  • This process differs from chemical vapor deposition (CVD) in the decomposition chemistry of the metal complex.
  • CVD chemical vapor deposition
  • ALD advanced vapor deposition
  • the complex undergoes pyrolytic decomposition on contact with the surface to give the desired film.
  • ALD atomic layer deposition
  • the complex is not completely decomposed to metal on contact with the surface. Rather, formation of the metal film takes place on introduction of a second reagent, which reacts with the deposited metal complex.
  • the second reagent is a reducing agent.
  • Advantages of an ALD process include the ability to control the film thickness and improved conformality of coverage because of the self-limiting adsorption of the precursor to the substrate surface in the first step of the process.
  • the ligands used in the ALD processes must also be stable with respect to decomposition and be able to desorb from the complex in a metal-free form. Following reduction of the copper, the ligand is liberated and must be removed from the surface to prevent its incorporation into the metal layer being formed.
  • U.S. Pat. No. 6,464,779 discloses a Cu atomic layer CVD process that requires treatment of a copper precursor containing both oxygen and fluorine with an oxidizing agent to form copper oxide, followed by treatment of the surface with a reducing agent.
  • WO 2004/036624 describes a two-step ALD process for forming copper layers comprising forming a copper oxide layer from a non-fluorine containing copper precursor on a substrate and reducing the copper oxide layer to form a copper layer on the substrate. Copper alkoxides, copper ⁇ -diketonates and copper dialkylamides are preferred copper precursors.
  • the reducing agent is a hydrogen (H 2 ) containing gas.
  • US 2003/0135061 discloses a dimeric copper(I) precursor which can be used to deposit metal or metal-containing films on a substrate under ALD or CVD conditions.
  • WO 2004/046417 describes the use of dimeric copper (I) complexes comprising amidinate ligands for use in an ALD process.
  • One aspect of this invention is a process for forming copper deposits on a substrate comprising:
  • Another aspect of the present invention is an article comprising a 1,3-diimine copper complex, (I), deposited on a substrate.
  • ALD atomic layer deposition
  • copper is deposited on a substrate by means of:
  • the present deposition process improves upon the processes described in the art by allowing the use of lower temperatures and producing higher quality, more uniform films.
  • the process of this invention also provides a more direct route to a copper film, avoiding the formation of an intermediate oxide film.
  • the copper can be deposited on the surface, or in or on porosity, of the substrate.
  • Suitable substrates include conducting, semiconducting and insulating substrates, including copper, silicon wafers, wafers used in the manufacture of ultra large scale integrated circuits, wafers prepared with dielectric material having a lower dielectric constant than silicon dioxide, and silicon dioxide and low k substrates coated with a barrier layer.
  • Barrier layers to prevent the migration of copper include tantalum, tantalum nitride, titanium, titanium nitride, tantalum silicon nitride, titanium silicon nitride, tantalum carbon nitride, and niobium nitride.
  • the processes of the invention can be conducted in solution, i.e., by contacting a solution of the copper complex with the reducing agent. However, it is preferred to expose the substrate to a vapor of the copper complex, and then remove any excess copper complex (i.e., undeposited complex) by vacuum or purging before exposing the deposited complex to a vapor of the reducing agent. After reduction of the copper complex, the free form of the ligand can be removed via vacuum, purging, heating, rinsing with a suitable solvent, or a combination of such steps.
  • This process can be repeated to build up thicker layers of copper, or to eliminate pin-holes.
  • the deposition of the copper complex is typically conducted at 0 to 200° C.
  • the reduction of the copper complex is typically carried out at similar temperatures, 0 to 200° C., more preferably 50 to 150° C.
  • Aggressive reducing agents are used to reduce the copper complex rapidly and completely. Suitable reducing agents are volatile and do not decompose on heating. They are also of sufficient reducing power to react rapidly on contact with the copper complex deposited on the substrate surface. Suitable reducing agents have been identified that have been used for copper(I) reduction in an ALD process.
  • One feature of these reagents is the presence of a proton donor.
  • the reducing agent is desirably able to transfer at least one electron to reduce the copper ion of the complex and at least one proton to protonate the ligand. It is also desirable that the oxidized reducing agent and the protonated ligand be able to be easily removed from the surface of the newly formed copper deposit.
  • the protonated ligand is removed by vacuum, by purging or by flushing the surface with a suitable solvent.
  • Suitable reducing agents for the copper deposition processes of this invention include 9-BBN, borane, diborane, dihydrobenzofuran, pyrazoline, germanes, diethylsilane, dimethylsilane, ethylsilane, phenylsilane, silane and disilane. Diethylsilane and silane are preferred.
  • the copper complexes are admitted to a reactor chamber containing the substrate under conditions of temperature, time and pressure to attain a suitable fluence of complex to the surface of the substrate.
  • time, T, P time, time and pressure
  • the undeposited complex vapor is pumped or purged from the chamber and the reducing agent is introduced into the chamber at a pressure of approximately 50 to 760 mTorr to reduce the adsorbed copper complex.
  • the substrate is held at a temperature between approximately 0 to 200 ° C. during reduction. With suitable combinations of copper complex and reducing agent, this reduction is rapid and substantially complete.
  • the reaction is at least 95% complete within an exposure time of from less than a second to several minutes. It is desired that the products from this reaction are readily removed from the surface of the substrate under the reducing conditions.
  • I copper ,3-diimine complex
  • This invention also provides novel 1,3-diimine copper complexes, (I),
  • L is selected from C 2 -C 15 olefins, C 2 -C 15 alkynes, nitriles, aromatic heterocycles, and phosphines;
  • R 1 and R 4 are independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, isobutyl, neopentyl and C 3 -C 5 alkylene;
  • R 2 , R 3 and R 5 are independently selected from hydrogen, fluorine, trifluoromethyl, phenyl, C 1 -C 10 alkyl and C 3 -C 5 alkylene, with the proviso that at least one of (R 1 , R 2 ) and (R 3 , R 4 ) taken together is —(CR 6 R 7 ) n —, where R 6 and R 7 are independently selected from hydrogen, fluorine, trifluoromethyl, C 1 -C 5 alkyl, and C 1 -C 5 alkyl ester, and n is 3, 4 or 5.
  • L is a linear, terminal olefin.
  • L can also be an internal olefin of cis- or trans-configuration; cis-configuration is preferred.
  • L can be a cyclic or bicyclic olefin.
  • L can also be substituted, for example with fluorine or silyl groups.
  • Suitable olefins include, but are not limited to, vinyltrimethylsilane, allyltrimethylsilane, 1-hexene, 4-methyl-1-pentene, 3,3-dimethyl-1-butene, and norbornene.
  • L can also be alkyne, nitrile, or an aromatic nitrogen heterocycle such as pyridine, pyrazine, triazine, or N-substituted imidazole, pyrazole, or triazole.
  • L can also be a phosphine.
  • Example 1 The synthesis of one ligand useful for making the copper complexes of this invention is given in Example 1 below.
  • a cyclic ketimine can be deprotonated by strong base, then treated with an electrophile such as an ester or acid halide derivative to provide the corresponding keto cyclic enamine as an intermediate.
  • Treatment of this intermediate with an alkylating agent such as dimethylsulfate, followed by the addition of a primary amine affords the desired cyclic diketimine.
  • the cyclic ketimine after deprotonation by strong base, can be directly coupled with an imidoyl derivative to provide the desired cyclic diketimine.
  • Other ligands can be prepared similarly.
  • this invention provides an article comprising a 1,3-diimine copper complex of structure (I), deposited on a substrate.
  • Suitable substrates include: copper, silicon wafers, wafers used in the manufacture of ultra-large scale integrated circuits, wafers prepared with dielectric material having a lower dielectric constant than silicon dioxide, and silicon dioxide and low k substrates coated with a barrier layer.
  • Barrier layers can be used to prevent the migration of copper into the substrate.
  • Suitable barrier layers include: tantalum, tantalum nitride, titanium, titanium nitride, tantalum silicon nitride, titanium silicon nitride, tantalum carbon nitride, and niobium nitride.
  • n-BuLi (2.89 M, 75.9 mL, 219.3 mmol) at ⁇ 78 ° C. under nitrogen. Once all the n-BuLi was added, the temperature was adjusted to ⁇ 5° C., and the reaction mixture was stirred for 30 min. Then a solution of 2-methyl-1-pyrroline (11.3 g, 135.7 mmol) in THF (15 mL) was added dropwise to the reaction mixture at ⁇ 5° C., and then stirred. After 30 min, ethylacetate (9.20 g, 104.4 mmol) was added dropwise over 30 min.
  • Pentane 100 mL was added to the residue, then the insoluble material was filtered. Concentration of the filtrate under reduced pressure, followed by vacuum distillation (31° C., 46 mTorr), afforded 4.2 g (76% yield) of product as a liquid.
  • This material is volatile at 55° C. under 500 mTorr, and was reduced to copper metal at 100° C. by exposure to diethylsilane as a reducing agent.
  • the viscous oil (vinyltrimethylsilane-[[2-(4,5-dihydro-3H-pyrrol-2-yl)-1-methyl-vinyl]-methylaminate]copper, prepared as described above) was used as a copper precursor to create a copper film on a substrate.
  • the substrate consisted of a silicon dioxide wafer with 250-Angstrom layer of tantalum on the silicon dioxide and a 100 Angstrom layer of copper on the tantalum.
  • Approximately 0.030 g of copper precursor was loaded in a dry box into a porcelain boat.
  • the boat and wafer ( ⁇ 1 cm 2 ) were placed in a glass tube approximately 3.5 inches apart.
  • the glass tube was removed from the dry box and attached to a vacuum line. Heating coils were attached to the glass tube surrounding both the area around the porcelain boat and the area around the wafer chip. This configuration allows the two areas to be maintained at different temperatures.
  • an argon gas flow was created through the tube, passing first over the sample in the boat and then over the wafer.
  • the pressure inside the tube was maintained at 120-200 mTorr.
  • the region around the wafer was warmed to 120° C. After approximately an hour, the temperature of the region around the sample boat was raised to 50° C.
  • the area around the sample boat was then cooled to room temperature.
  • the tube was evacuated to a pressure of ⁇ 10 mTorr and was back-filled with diethylsilane.
  • the area of the tube at 110° C. quickly turned a copper color.
  • the apparatus was cooled and returned to the dry box. The copper color was perceptively darker. The process was repeated to yield a wafer with a smooth copper film.
  • 2-(1-pyrrolin-2-ylmethylene)piperidine (0.328 g, 2 mmol) was treated with t-BuLi (1.7 M, 1.17 mL, 2 mmol) in ether (15 mL), and the mixture was stirred at room temperature for 20 min.
  • t-BuLi 1.7 M, 1.17 mL, 2 mmol
  • ether 15 mL
  • Cu[(CH 3 CN) 4 ]SO 3 CF 3 (0.75 g, 2 mmol) and vinyltrimethylsilane (1 g, 10 mmol) were mixed together in ether (15 mL), and the resultant mixture was stirred at room temperature for 20 min.
  • the piperidine solution was added to the copper solution, and the resultant mixture was stirred at room temperature for 1 h.

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US11/658,368 2004-07-30 2005-07-29 Copper (I) Complexes for Deposition of Copper Films by Atomic Layer Deposition Abandoned US20080299322A1 (en)

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US59278504P 2004-07-30 2004-07-30
US59281604P 2004-07-30 2004-07-30
US11/658,368 US20080299322A1 (en) 2004-07-30 2005-07-29 Copper (I) Complexes for Deposition of Copper Films by Atomic Layer Deposition
PCT/US2005/027019 WO2006015225A1 (en) 2004-07-30 2005-07-29 Copper (ii) complexes for deposition of copper films by atomic layer deposition

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US11/658,369 Expired - Fee Related US7619107B2 (en) 2004-07-30 2005-07-29 Copper (II) complexes for deposition of copper films by atomic layer deposition

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US (2) US20080299322A1 (ko)
EP (2) EP1771594A1 (ko)
JP (2) JP2008508427A (ko)
KR (2) KR20070048215A (ko)
IL (2) IL180764A0 (ko)
TW (2) TW200622024A (ko)
WO (2) WO2006015200A1 (ko)

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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
US7851360B2 (en) * 2007-02-14 2010-12-14 Intel Corporation Organometallic precursors for seed/barrier processes and methods thereof
US7858525B2 (en) * 2007-03-30 2010-12-28 Intel Corporation Fluorine-free precursors and methods for the deposition of conformal conductive films for nanointerconnect seed and fill
DE102007058571B4 (de) * 2007-12-05 2012-02-16 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Substrat mit einer Kupfer enthaltenden Beschichtung und Verfahren zu deren Herstellung mittels Atomic Layer Deposition und Verwendung des Verfahrens
JP2012532993A (ja) 2009-07-10 2012-12-20 レール・リキード−ソシエテ・アノニム・プール・レテュード・エ・レクスプロワタシオン・デ・プロセデ・ジョルジュ・クロード 銅含有膜の堆積のためのビス−ケトイミナート銅前駆体
WO2013188377A1 (en) * 2012-06-11 2013-12-19 Wayne State University Precursors for atomic layer deposition
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EP1771595A1 (en) 2007-04-11
EP1771594A1 (en) 2007-04-11
US7619107B2 (en) 2009-11-17
TW200617198A (en) 2006-06-01
WO2006015200A1 (en) 2006-02-09
IL180768A0 (en) 2007-06-03
IL180764A0 (en) 2007-06-03
JP2008508426A (ja) 2008-03-21
KR20070043865A (ko) 2007-04-25
TW200622024A (en) 2006-07-01
WO2006015225A1 (en) 2006-02-09
JP2008508427A (ja) 2008-03-21
KR20070048215A (ko) 2007-05-08
US20080044687A1 (en) 2008-02-21

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