WO2019023797A1 - Organometallic compounds and methods for the deposition of high purity tin oxide - Google Patents

Organometallic compounds and methods for the deposition of high purity tin oxide Download PDF

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Publication number
WO2019023797A1
WO2019023797A1 PCT/CA2018/050933 CA2018050933W WO2019023797A1 WO 2019023797 A1 WO2019023797 A1 WO 2019023797A1 CA 2018050933 W CA2018050933 W CA 2018050933W WO 2019023797 A1 WO2019023797 A1 WO 2019023797A1
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WO
WIPO (PCT)
Prior art keywords
group
organometallic compound
substrate
netme
formula
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/CA2018/050933
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English (en)
French (fr)
Inventor
Rajesh Odedra
Cunhai Dong
Diana Fabulyak
Wesley GRAFF
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.)
Seastar Chemicals ULC
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Seastar Chemicals ULC
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 Seastar Chemicals ULC filed Critical Seastar Chemicals ULC
Priority to CN201880050021.0A priority Critical patent/CN111032667B/zh
Priority to JP2020505377A priority patent/JP2020530199A/ja
Priority to SG11202000884RA priority patent/SG11202000884RA/en
Priority to KR1020207006021A priority patent/KR102715899B1/ko
Publication of WO2019023797A1 publication Critical patent/WO2019023797A1/en
Priority to US16/442,930 priority patent/US20190337969A1/en
Anticipated expiration legal-status Critical
Priority to US16/834,361 priority patent/US11643422B2/en
Priority to US17/213,328 priority patent/US20210214379A1/en
Priority to JP2022194698A priority patent/JP7577104B2/ja
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C07F7/2284—Compounds with one or more Sn-N linkages
    • 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
    • C23C16/22—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 inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40—Oxides
    • C23C16/407—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
    • 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]
    • C23C16/45527—Atomic layer deposition [ALD] characterized by the ALD cycle, e.g. different flows or temperatures during half-reactions, unusual pulsing sequence, use of precursor mixtures or auxiliary reactants or activations
    • C23C16/45536—Use of plasma, radiation or electromagnetic fields
    • 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
    • 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
    • C23C16/50—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 using electric discharges
    • C23C16/505—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 using electric discharges using radio frequency discharges
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/161—Coating processes; Apparatus therefor using a previously coated surface, e.g. by stamping or by transfer lamination
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/167—Coating processes; Apparatus therefor from the gas phase, by plasma deposition

Definitions

  • This new conformal deposition layer can server 2 major functions:
  • each R group is independently selected from the group consisting of an alkyl or aryl group having from 1 to 10 carbon atoms;
  • each R' group is independently selected from the group consisting of an alkyl, acyl or aryl group having from 1 to 10 carbon atoms;
  • Figure 3 is a process flow diagram depicting a method for depositing a tin oxide film
  • Figure 4 is a schematic representation of a spacer-defined double-patterning technique.
  • Figure 6 shows the NMR spectrum of Sn(NMe 2 )4.
  • Figure 20 shows the NMR of the reaction of (NMe 2 Sn with ethanol.
  • Figure 21 shows the NMR of the reaction of Me3Sn Me2 with water.
  • each R group is independently selected from the group consisting of an alkyl or aryl group having from 1 to 10 carbon atoms;
  • Compounds of Formula I are thermally stable whilst exhibiting good reactivity. Thus, delivery of the compound to the deposition chamber will take place without decomposition occurring, (decomposition results in a deposited film which will not be uniform).
  • a good stability and reactivity profile as demonstrated by the compounds of the invention, also means that less material is required to be delivered to the growth chamber (less material is more economic), and cycling will be faster (as there will be less material left in the chamber at the end of the process to be pumped off), meaning that thicker films can be deposited in shorter times, so increasing throughput.
  • ALD can be carried out at much lower temperatures (or using a wider temperature window) using compounds of Formula I than processes of the art. Thermal stability also means that material can be purified much more easily after synthesis, and handling becomes easier.
  • a RF plasma source 806 is coupled to the chamber body 801 and configured to generate a plasma 840 in the processing chamber 800.
  • a gas source 888 is coupled to the processing chamber 800 to supply a gas to the interior processing region 809.
  • a gas include, but are not limited to, oxidants such as 02, 03, NO, N02, C02, H202, and H20.
  • the plasma source 806 may generate the plasma 840 by exciting and ionizing the gas provided to the processing chamber 800. Ions in the plasma 840 may be attracted across the plasma sheath 842 by different mechanisms.
  • a bias source 890 is coupled to the substrate support 834 configured to bias the substrate 838 to attract ions 802 from the plasma 840 across the plasma sheath 842.
  • the bias source 890 may be a DC power supply to provide a DC voltage bias signal or an RF power supply to provide an RF bias signal.
  • the pattern is then transferred through material layer 844 using the tin oxide layer 847 as a hardmask.
  • an etchant is used that selectively removes material layer 844 over the tin oxide layer 847.
  • the tin oxide layer 847 can optionally be stripped from the substrate 834.
  • a plasma is generated in the interior processing volume, allowing the compound of Formula I to react with the ionized oxidizing gases to form a tin oxide layer on the material layer.
  • Bu2Sn(OMe)2 To Bu2Sn(OMe)2 was added water. Reaction took place spontaneously. The clear Bu2Sn(OMe)2 turned cloudy and a white solid formed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Metallurgy (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Plasma & Fusion (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Electromagnetism (AREA)
  • Structural Engineering (AREA)
  • Architecture (AREA)
  • Chemical Vapour Deposition (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Formation Of Insulating Films (AREA)
PCT/CA2018/050933 2017-08-02 2018-07-31 Organometallic compounds and methods for the deposition of high purity tin oxide Ceased WO2019023797A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CN201880050021.0A CN111032667B (zh) 2017-08-02 2018-07-31 有机金属化合物和所述有机金属化合物的纯化
JP2020505377A JP2020530199A (ja) 2017-08-02 2018-07-31 高純度酸化スズの堆積のための有機金属化合物及び方法
SG11202000884RA SG11202000884RA (en) 2017-08-02 2018-07-31 Organometallic compounds and methods for the deposition of high purity tin oxide
KR1020207006021A KR102715899B1 (ko) 2017-08-02 2018-07-31 유기금속 화합물 및 유기금속 화합물의 정제
US16/442,930 US20190337969A1 (en) 2017-08-02 2019-06-17 Organometallic compounds and methods for the deposition of high purity tin oxide
US16/834,361 US11643422B2 (en) 2017-08-02 2020-03-30 Organometallic compounds and purification of such organometallic compounds
US17/213,328 US20210214379A1 (en) 2017-08-02 2021-03-26 Organometallic compounds and purification of such organometallic compounds
JP2022194698A JP7577104B2 (ja) 2017-08-02 2022-12-06 有機金属化合物及びその精製法

Applications Claiming Priority (2)

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CA2975104 2017-08-02
CA2975104A CA2975104A1 (en) 2017-08-02 2017-08-02 Organometallic compounds and methods for the deposition of high purity tin oxide

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US (3) US20190337969A1 (enExample)
JP (2) JP2020530199A (enExample)
KR (1) KR102715899B1 (enExample)
CN (1) CN111032667B (enExample)
CA (1) CA2975104A1 (enExample)
SG (1) SG11202000884RA (enExample)
TW (2) TW201920214A (enExample)
WO (1) WO2019023797A1 (enExample)

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US11300876B2 (en) 2018-06-21 2022-04-12 Inpria Corporation Stable solutions of monoalkyl tin alkoxides and their hydrolysis and condensation products
WO2022165381A1 (en) * 2021-01-29 2022-08-04 Entegris, Inc. Process for preparing organotin compounds
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US11498934B2 (en) 2019-01-30 2022-11-15 Inpria Corporation Monoalkyl tin trialkoxides and/or monoalkyl tin triamides with particulate contamination and corresponding methods
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US11673903B2 (en) 2018-04-11 2023-06-13 Inpria Corporation Monoalkyl tin compounds with low polyalkyl contamination, their compositions and methods
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US11966158B2 (en) 2019-01-30 2024-04-23 Inpria Corporation Monoalkyl tin trialkoxides and/or monoalkyl tin triamides with low metal contamination and/or particulate contamination, and corresponding methods
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