WO1998022568A1 - Formulation de decapage contenant catechol, hydroxylamine, eau et amines autres que alcanolamines, destinee au nettoyage des plaquettes ayant subi un brulage au plasma - Google Patents

Formulation de decapage contenant catechol, hydroxylamine, eau et amines autres que alcanolamines, destinee au nettoyage des plaquettes ayant subi un brulage au plasma Download PDF

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Publication number
WO1998022568A1
WO1998022568A1 PCT/US1997/021450 US9721450W WO9822568A1 WO 1998022568 A1 WO1998022568 A1 WO 1998022568A1 US 9721450 W US9721450 W US 9721450W WO 9822568 A1 WO9822568 A1 WO 9822568A1
Authority
WO
WIPO (PCT)
Prior art keywords
cleaning formulation
groups
group
aikanolamine
hydroxylamine
Prior art date
Application number
PCT/US1997/021450
Other languages
English (en)
Inventor
George Guan
William A. Wojtczak
Stephen A. Fine
Original Assignee
Advanced Chemical Systems International, 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 Advanced Chemical Systems International, Inc. filed Critical Advanced Chemical Systems International, Inc.
Publication of WO1998022568A1 publication Critical patent/WO1998022568A1/fr

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Classifications

    • 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
    • H01L21/02041—Cleaning
    • H01L21/02043—Cleaning before device manufacture, i.e. Begin-Of-Line process
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3218—Alkanolamines or alkanolimines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3263—Amides or imides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5022—Organic solvents containing oxygen
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
    • C11D2111/22—
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen

Definitions

  • the present invention relates generally to chemical formulations used in semiconductor wafer fabrication and particularly to chemical formulations that are utilized to remove residue from wafers following a resist plasma ashing step.
  • the prior art teaches the utilization of various chemical formulations to remove residue and clean wafers following a photoresist ashing step.
  • these prior art chemical formulations include strong reagents such as strong acids or strong bases to help remove unwanted inorganic residues.
  • strong reagents can cause unwanted further removal of metal or insulator layers remaining on the wafer and are therefore undesirable in many instances.
  • chemical formulations which effectively remove residue following a resist ashing step which do not attack and potentially degrade delicate structures which are meant to remain on a wafer.
  • the present invention comprises formulations for stripping wafer residues which originate from high density plasma metal etching followed by plasma ashing.
  • the formulations contain hydroxylamine, water, catechol, and amines other than alkanolamines.
  • the preferred formulations utilize the following components (percentages are by weight):
  • Catechol or a 1 ,3-dicarbonyi chelating agent 0-20% (the preferred range is 0.9-9%) Water 8-68% (the preferred range is 8-44%)
  • a non-alkanolamine 10-78% (the preferred range is 30-55%)
  • the preferred non-alkanolamines are secondary and/or tertiary amines, including: 3,3' -Iminobis (N,N-dimethylpropylamine) Pentamethyldiethylenetriamine Triethylamine
  • the preferred 1 ,3-dicarbonyl chelating agents are:
  • Typical steps in the fabrication of semiconductor wafers involve the creation of metalized layers or insulating layers having patterned resists layers formed thereon. Such a wafer may then be exposed to plasmas (such as halogen based plasmas) to remove exposed metal or insulator. Thereafter, a plasma ashing step is conducted (typically using an oxygen based plasma) in which the remaining resist is removed from the wafer. The result is a patterned metal layer or a patterned insulator layer.
  • plasmas such as halogen based plasmas
  • the residue following the plasma ashing step is predominantly composed of inorganic compounds such as metal halides and metal oxides.
  • the present invention comprises chemical formulations for the removal of inorganic compound residues, where the formulations do not contain strong acids or strong bases of the prior art formulations.
  • the general formulations of the present invention contain hydroxylamine, water, catechol (or a 1 ,3-dicarbonyl chelating agent), and amines other than alkanolamines.
  • the preferred formulations utilize the following components (percentages are by weight): Catechol (or a 1 ,3-dicarbonyl chelating agent) 0-20% (the preferred range is 0.9-9%)
  • a non-alkanolamine 10-78% (the preferred range is 30-55%)
  • the preferred 1 ,3-dicarbonyl chelating agents are:
  • the preferred non-alkanolamines are secondary and/or tertiary amines, including:
  • the invention further includes other non-alkanolamines, including:
  • non-alkanolamines of the following general formula In addition to the preferred secondary and tertiary non-alkanolamines identified above, the inventors expect non-alkanolamines of the following general formula to be suitable:
  • R1 R2R3-N in which: a. No more than one of the three R groups may be H. b. At least two of the R groups are directly attached to the Nitrogen atom via a carbon atom. c. None of the R groups contain an alkanol OH moiety.
  • catechol-related chelating agents include derivatives of benzene, naphthalene, and aromatic heterocyclic compounds having at least two hydroxyl (OH) groups on adjacent carbon atoms.
  • 1 ,3-dicarbonyl chelating agents listed above other 1 ,3-dicarbonyl chelating agents are expected to exhibit comparable functionality. These include, but are not limited to, diketones, diesters, diamides, keto-esters, keto-amides, and ester-amides.
  • Other functional groups may replace one or both carbonyl groups and be expected to exhibit similar properties if they are strongly electron withdrawing. These include cyano, nitro, and sulfonyl groups, among others. It is also expected by the inventors that inclusion of optional components such as surfactants, stabilizers, corrosion inhibitors, buffering agents, and organic cosolvents would constitute obvious additions to those practiced in the art.
  • the formulations of the present invention are particularly useful on wafers which have been etched with chlorine- or fluorine-containing plasmas followed by oxygen plasma ashing.
  • the residues generated by this type of processing typically contain inorganic materials such as, but not limited to, aluminum oxide, aluminum fluoride and titanium oxide. When these residues have high densities it is often difficult to dissolve them completely without causing corrosion of metal and titanium nitride features required for effective device performance.
  • Example 1 A first wafer included 0.8 micron diameter, four layer vias comprised of silicon oxide top and second layers, a third layer of titanium nitride, and a bottom layer of aluminum, silicon, copper (AlSiCu) alloy.
  • the substrate was silicon oxide.
  • Example 2 A second wafer included 1.0 micron diameter, two-layer vias comprised of a top layer of silicon oxide (7000 Angs. thick) and a middle layer of titanium nitride (1200 Angs. thick) on top of a silicon substrate.
  • a specific formulation that was evaluated utilizing the second wafer structure is:
  • Example 3 A third wafer included 1.6 micron diameter, three-layer vias comprised of a top layer of titanium nitride (40 nanometers thick), a middle layer of silicon oxide (1.3 microns thick), and a bottom layer of aluminum (99%) / copper (1 %) alloy.
  • the substrate was silicon oxide.

Abstract

Cette invention se rapporte à une formulation utilisée dans la fabrication de semi-conducteurs pour le nettoyage des plaquettes de semi-conducteurs, après le brûlage au plasma. Ladite formulation contient les composants suivants: du catéchol ou un agent chélatant de 1,3-dicarbonyle, de l'eau, de l'hydroxylamine et une amine non alcanolamine. Les amines préférées, autres que alcanolamines, sont des amines secondaires et/ou tertiaires, et notamment 3,3'-iminobis (N,N-diméthylpropylamine), pentaméthyldiéthylènetriamine et triéthylamine. Les agents chélatants de 1,3-dicarbonyle préférés sont 2,4-pentanedione et acétoacétate de méthyle.
PCT/US1997/021450 1996-11-22 1997-11-21 Formulation de decapage contenant catechol, hydroxylamine, eau et amines autres que alcanolamines, destinee au nettoyage des plaquettes ayant subi un brulage au plasma WO1998022568A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3206596P 1996-11-22 1996-11-22
US60/032,065 1996-11-22

Publications (1)

Publication Number Publication Date
WO1998022568A1 true WO1998022568A1 (fr) 1998-05-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/021450 WO1998022568A1 (fr) 1996-11-22 1997-11-21 Formulation de decapage contenant catechol, hydroxylamine, eau et amines autres que alcanolamines, destinee au nettoyage des plaquettes ayant subi un brulage au plasma

Country Status (1)

Country Link
WO (1) WO1998022568A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6211126B1 (en) * 1997-12-23 2001-04-03 Advanced Technology Materials, Inc. Formulations including a 1, 3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates
WO2001040425A2 (fr) * 1999-11-16 2001-06-07 Esc, Inc. Composition nettoyante post planarisation chimicomecanique
US6566315B2 (en) 2000-12-08 2003-05-20 Advanced Technology Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
EP1349969A1 (fr) * 2000-12-08 2003-10-08 Advanced Technology Materials, Inc. Compositions semi-conductrices de d capage contenant des composes 1,3 dicarbonyle
EP1627259A1 (fr) * 2003-05-23 2006-02-22 Air Products And Chemicals, Inc. Compositions adaptees pour eliminer une photoresine, des produits derives de la photoresine et des residus de gravure, et utilisations
TWI580776B (zh) * 2014-12-23 2017-05-01 氣體產品及化學品股份公司 具有改良的矽鈍化性之光阻劑或半導體製造殘留物的半水性剝除及清潔組合物
CN108121176A (zh) * 2016-11-29 2018-06-05 安集微电子科技（上海）股份有限公司 一种低刻蚀光阻残留物清洗液

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4617251A (en) * 1985-04-11 1986-10-14 Olin Hunt Specialty Products, Inc. Stripping composition and method of using the same
US4626411A (en) * 1984-04-18 1986-12-02 Dearborn Chemical Company, Limited Composition and method for deoxygenation
US4938839A (en) * 1986-02-14 1990-07-03 Fujitsu Limited Method of removing photoresist on a semiconductor wafer
US5279771A (en) * 1990-11-05 1994-01-18 Ekc Technology, Inc. Stripping compositions comprising hydroxylamine and alkanolamine
US5417877A (en) * 1991-01-25 1995-05-23 Ashland Inc. Organic stripping composition
US5419779A (en) * 1993-12-02 1995-05-30 Ashland Inc. Stripping with aqueous composition containing hydroxylamine and an alkanolamine
EP0662705A2 (fr) * 1994-01-07 1995-07-12 Mitsubishi Gas Chemical Company, Inc. Agent de nettoyage pour composant semi-conducteur et procédé de fabrication d'un composant semi-conducteur
EP0680078A2 (fr) * 1994-03-28 1995-11-02 Mitsubishi Gas Chemical Company, Inc. Traitement de surface pour substrat semi-conducteur
US5496491A (en) * 1991-01-25 1996-03-05 Ashland Oil Company Organic stripping composition
US5507978A (en) * 1995-05-08 1996-04-16 Ocg Microelectronic Materials, Inc. Novolak containing photoresist stripper composition
US5545353A (en) * 1995-05-08 1996-08-13 Ocg Microelectronic Materials, Inc. Non-corrosive photoresist stripper composition
US5556482A (en) * 1991-01-25 1996-09-17 Ashland, Inc. Method of stripping photoresist with composition containing inhibitor
US5561105A (en) * 1995-05-08 1996-10-01 Ocg Microelectronic Materials, Inc. Chelating reagent containing photoresist stripper composition
US5563119A (en) * 1995-01-26 1996-10-08 Ashland Inc. Stripping compositions containing alkanolamine compounds
US5580846A (en) * 1994-01-28 1996-12-03 Wako Pure Chemical Industries, Ltd. Surface treating agents and treating process for semiconductors
US5597420A (en) * 1995-01-17 1997-01-28 Ashland Inc. Stripping composition having monoethanolamine
US5612304A (en) * 1995-07-07 1997-03-18 Olin Microelectronic Chemicals, Inc. Redox reagent-containing post-etch residue cleaning composition
US5648324A (en) * 1996-01-23 1997-07-15 Ocg Microelectronic Materials, Inc. Photoresist stripping composition

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* Cited by examiner, † Cited by third party
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US4626411A (en) * 1984-04-18 1986-12-02 Dearborn Chemical Company, Limited Composition and method for deoxygenation
US4617251A (en) * 1985-04-11 1986-10-14 Olin Hunt Specialty Products, Inc. Stripping composition and method of using the same
US4938839A (en) * 1986-02-14 1990-07-03 Fujitsu Limited Method of removing photoresist on a semiconductor wafer
US5279771A (en) * 1990-11-05 1994-01-18 Ekc Technology, Inc. Stripping compositions comprising hydroxylamine and alkanolamine
US5334332A (en) * 1990-11-05 1994-08-02 Ekc Technology, Inc. Cleaning compositions for removing etching residue and method of using
US5556482A (en) * 1991-01-25 1996-09-17 Ashland, Inc. Method of stripping photoresist with composition containing inhibitor
US5417877A (en) * 1991-01-25 1995-05-23 Ashland Inc. Organic stripping composition
US5496491A (en) * 1991-01-25 1996-03-05 Ashland Oil Company Organic stripping composition
US5419779A (en) * 1993-12-02 1995-05-30 Ashland Inc. Stripping with aqueous composition containing hydroxylamine and an alkanolamine
EP0662705A2 (fr) * 1994-01-07 1995-07-12 Mitsubishi Gas Chemical Company, Inc. Agent de nettoyage pour composant semi-conducteur et procédé de fabrication d'un composant semi-conducteur
US5580846A (en) * 1994-01-28 1996-12-03 Wako Pure Chemical Industries, Ltd. Surface treating agents and treating process for semiconductors
EP0680078A2 (fr) * 1994-03-28 1995-11-02 Mitsubishi Gas Chemical Company, Inc. Traitement de surface pour substrat semi-conducteur
US5597420A (en) * 1995-01-17 1997-01-28 Ashland Inc. Stripping composition having monoethanolamine
US5563119A (en) * 1995-01-26 1996-10-08 Ashland Inc. Stripping compositions containing alkanolamine compounds
US5507978A (en) * 1995-05-08 1996-04-16 Ocg Microelectronic Materials, Inc. Novolak containing photoresist stripper composition
US5545353A (en) * 1995-05-08 1996-08-13 Ocg Microelectronic Materials, Inc. Non-corrosive photoresist stripper composition
US5561105A (en) * 1995-05-08 1996-10-01 Ocg Microelectronic Materials, Inc. Chelating reagent containing photoresist stripper composition
US5612304A (en) * 1995-07-07 1997-03-18 Olin Microelectronic Chemicals, Inc. Redox reagent-containing post-etch residue cleaning composition
US5648324A (en) * 1996-01-23 1997-07-15 Ocg Microelectronic Materials, Inc. Photoresist stripping composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PROCEEDINGS OF SPIE, Volume 3049, March 1997, LOUIS D. et al., "Wafer Cleaning Process after Plasma Metal Etch", pages 1010-1023. *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6211126B1 (en) * 1997-12-23 2001-04-03 Advanced Technology Materials, Inc. Formulations including a 1, 3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates
US6660700B2 (en) 1999-08-20 2003-12-09 Advanced Technologies Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
WO2001040425A2 (fr) * 1999-11-16 2001-06-07 Esc, Inc. Composition nettoyante post planarisation chimicomecanique
WO2001040425A3 (fr) * 1999-11-16 2002-01-03 Esc Inc Composition nettoyante post planarisation chimicomecanique
US6566315B2 (en) 2000-12-08 2003-05-20 Advanced Technology Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
EP1349969A1 (fr) * 2000-12-08 2003-10-08 Advanced Technology Materials, Inc. Compositions semi-conductrices de d capage contenant des composes 1,3 dicarbonyle
EP1349969A4 (fr) * 2000-12-08 2004-07-28 Advanced Tech Materials Compositions semi-conductrices de d capage contenant des composes 1,3 dicarbonyle
KR100890418B1 (ko) * 2000-12-08 2009-03-26 어드밴스드 테크놀러지 머티리얼즈, 인코포레이티드 1,3-디카르보닐 화합물을 포함하는 반도체 스트리핑 조성물
EP1627259A1 (fr) * 2003-05-23 2006-02-22 Air Products And Chemicals, Inc. Compositions adaptees pour eliminer une photoresine, des produits derives de la photoresine et des residus de gravure, et utilisations
EP1627259A4 (fr) * 2003-05-23 2009-04-01 Air Prod & Chem Compositions adaptees pour eliminer une photoresine, des produits derives de la photoresine et des residus de gravure, et utilisations
TWI580776B (zh) * 2014-12-23 2017-05-01 氣體產品及化學品股份公司 具有改良的矽鈍化性之光阻劑或半導體製造殘留物的半水性剝除及清潔組合物
CN108121176A (zh) * 2016-11-29 2018-06-05 安集微电子科技（上海）股份有限公司 一种低刻蚀光阻残留物清洗液

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