WO1998045399A1 - Ethylenediaminetetraacetic acid or its ammonium salt semiconductor process residue removal composition and process - Google Patents

Ethylenediaminetetraacetic acid or its ammonium salt semiconductor process residue removal composition and process Download PDF

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Publication number
WO1998045399A1
WO1998045399A1 PCT/US1998/005150 US9805150W WO9845399A1 WO 1998045399 A1 WO1998045399 A1 WO 1998045399A1 US 9805150 W US9805150 W US 9805150W WO 9845399 A1 WO9845399 A1 WO 9845399A1
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WIPO (PCT)
Prior art keywords
substrate
composition
residue
polymeric material
removing photoresist
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/US1998/005150
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English (en)
French (fr)
Inventor
Wai Mun Lee
Zhefei Jessie Chen
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.)
EKC Technology Inc
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EKC Technology Inc
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Filing date
Publication date
Application filed by EKC Technology Inc filed Critical EKC Technology Inc
Priority to EP98911697A priority Critical patent/EP0975731B1/en
Priority to JP54278298A priority patent/JP4138891B2/ja
Priority to KR19997009102A priority patent/KR100386137B1/ko
Priority to DE69835951T priority patent/DE69835951T2/de
Publication of WO1998045399A1 publication Critical patent/WO1998045399A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
    • B24B37/00—Lapping machines or devices; Accessories
    • B24B37/04—Lapping machines or devices; Accessories designed for working plane surfaces
    • B24B37/042—Lapping machines or devices; Accessories designed for working plane surfaces operating processes therefor
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    • C11D2111/22—Electronic devices, e.g. PCBs or semiconductors
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/24—Mineral surfaces, e.g. stones, frescoes, plasters, walls or concretes

Definitions

  • the present invention relates generally to a cleaning composition and process for removal of organic, organometallic and metal oxide residues from substrates. More particularly, it relates to such a composition and process for removing semiconductor device fabrication residues from semiconductor device substrates, such as etching residues after plasma etching processes in the fabrication of integrated circuits on silicon wafers and similar processes. Most especially, it relates to such a composition and process which is effective for the removal of these materials while avoiding substantial attack on metal or insulation layers employed in integrated circuits, including titanium layers.
  • Oxygen plasma oxidation is often used for removal of photoresist or other polymeric materials after their use during the fabrication process has been completed.
  • Such high energy processes typically result in the formation of organometallic and other residues on sidewalls of the structures being formed in the fabrication process.
  • a variety of metal and other layers are commonly employed in integrated circuit fabrication, including aluminum, aluminum/silicon/copper, titanium, titanium nitride, titanium/tungsten, tungsten, silicon oxide, poly silicon crystal, and the like. The use of such different layers results in the formation of different organometallic residues in the high energy processes.
  • cleaning compositions should also not attack the different metallurgies or insulators used in integrated circuit fabrication.
  • a variety of residue removal compositions and processes suitable for integrated circuit fabrication have been developed and marketed by EKC Technology, Inc., the assignee of the present application. Some of these compositions and processes are also useful for stripping photoresist, polyamide or 15 other polymeric layers from substrates in integrated circuit fabrication, and EKC has also developed a variety of compositions and processes for stripping such polymeric layers from substrates in integrated circuit fabrication.
  • Such compositions and processes are disclosed in the following commonly assigned issued patents: U.S. Patent 5,482,566, issued January 9, 1996 to Lee; U.S. Patent 5,399,464, issued March 21, 1995 to Lee; U.S.
  • Patent 5,381,807 issued January 17, 1995 to Lee; U.S. Patent 5,334,332, issued August 2, 1994 to Lee; U.S. Patent 5,279,771, issued January 18, 1994 to Lee; U.S. Patent 4,824,763, issued April 25, 1989 to Lee and U.S. Patent 4,395,348, issued July 26, 1983 to Lee.
  • These compositions have achieved substantial success in integrated circuit fabrication applications.
  • further development of integrated circuits and their fabrication processes have created a need for improvement in residue removal compositions and processes.
  • etching residue removal and substrate compatibility with chemicals employed in wet processing is becoming more and more critical for obtaining acceptable yield in very large scale integration (VLSI) and ultra large scale integration (ULSI) processes.
  • VLSI very large scale integration
  • ULSI ultra large scale integration
  • the composition of such etching residue is generally made up of the etched substrates, underlying substrate, photoresist and etching gases.
  • the substrate compatibility of the wafers with wet chemicals is highly dependent on the processing of the polysilicon, multilevel interconnection dielectric layers and metallization in thin film deposition, etching and post-etch treatment of the wafers, which are often quite different from one fabrication process to another.
  • Titanium has become more widely used in semiconductor manufacturing processes. It is employed both as a barrier layer to 10 prevent electromigration of certain atoms and as an antireflectire layer on top of other metals.
  • a residue removal composition in accordance with this invention comprises ethylenediaminetetraacetic acid or a mono- di- tri- or tetraammonium salt thereof and water or a polar organic solvent.
  • a process for removing a residue from a substrate in accordance with this invention comprises contacting the substrate with a composition that contains ethylenediaminetetraacetic acid or a mono- di- tri- or tetraammonium salt thereof for a time and at a temperature sufficient to remove the residue from the substrate.
  • the ethylenediaminetetraacetic acid is used in its acid form, it can either be employed alone as the principal active ingredient or in combination with ammonia to form ammonium salt in situ.
  • ethylenediaminetetraacetic acid or a mono- di- tri- or tetraammonium salt thereof gives a residue removing composition that attacks titanium, for example, at least about 3 times less' than prior compositions.
  • the ethylenediaminetetraacetic acid or a mono- di-tri- or tetraammonium salt thereof containing composition gives at least equivalent performance as a residue removing composition to prior art cleaning compositions.
  • Figures 1A-8C are scanning electron microscope (SEM) photographs showing comparative results achieved using the composition and process of the present invention.
  • ethylenediaminetetraacetic acid (EDTA) or a mono- di- tri- or tetraammonium salt thereof suitable for use in the invention preferably have relatively high decomposition temperatures.
  • Preferred higher decomposition temperature specific examples of such EDTA salts include diammonium EDTA and tetraammonium EDTA.
  • the composition desirably contains at least about 1 to 50 % by weight of at least one ethylenediaminetetraacetic acid or a mono- di- tri- or tetraammonium salt thereof; optionally, from about 25 % to about 75% by weight of one or more amines or alkanolamines; optionally, from about 25 % to about 75 % percent by weight of an organic polar solvent; optionally, from about 0.15% to about 10% by weight of an organic or inorganic ammonium salt; optionally, from about 5 % to about 25 % by weight of an additional chelating agent, such as catechol or gallic acid; and from about 25% to about 75% by weight of water (e.g., as part of the EDTA or its ammonium salt).
  • the composition may optionally contain from about 1 % to about 10% percent by weight of ammonia.
  • Ethylenediaminetetraacetic acid is one of the most widely used chelating agents in the world. Its ammonium salts, soluble in water and most of the organic solvents, should be stronger chelants than EDTA due to extra ammonium chelating sites. These organic ammonium salts are good starting chemicals for ammonium based integrated circuit cleaning formulations.
  • Suitable amines for the composition include ethylene diamine, diethylene triamine, 2-methyleneaminopropylenediamine, and the like.
  • alkanolamines examples include monoethanolamine, diethanolamine, triethanolamine, tertiarybutyldiethanolamine, isopropanolamine, diisopropanolamine (2-amino-l-propanol, l-amino-2-propanol), triisopropanolamine, 3-amino-l-propanol, isobutanolamine, 2-(2- aminoethoxy)ethanol (diglycolamine), 2-amino-2-ethoxy-propanol, methylethanol amine, N,N-diethylene hydroxylamine, and the like.
  • Suitable examples of polar solvents for the composition, in addition to water include dimethyl sulfoxide, ethylene glycol, ethylene glycol alkyl ether, diethylene glycol alkyl ether, triethylene glycol alkyl ether, propylene glycol, propylene glycol alkyl ether, N-substituted pyrrolidone, sulfolane, dimethyl acetamide, and the like. Additional polar solvents as known in the art can also be used in the composition of the present invention.
  • ammonium salts for the composition include organic ammonium salts in addition to EDTA ammonium salts, such as ammonium tartrate, ammonium citrate, ammonium formate; ammonium glucomate; inorganic ammonium salts, such as ammonium fluoride, ammonium nitrate, ammonium thiosulfate, ammonium persulfate, ammonium bicarbonate, ammonium phosphate, and the like.
  • the residue cleaning compositions of the present composition are effective in removing organometallic and metal oxide residue from a variety of integrated circuit silicon wafer substrates, including metal layers, such as aluminum or titanium, oxide layers, such as silicon oxides, nitride layers, such as silicon nitride, and the like.
  • the cleaning compositions of the present invention are also effective in removing organometallic and metal oxide residue generated on the substrate of etching equipment utilized in the fabrication of integrated circuits. Examples of commercially available etching equipment include that available from
  • the method of cleaning a substrate using the cleaning compositions of the present invention involves contacting a substrate having organometallic and metal oxide residue thereon with a stripping and cleaning composition of the present invention for a time and at a temperature sufficient to remove the residue.
  • the substrate is generally immersed in the stripping and cleaning composition.
  • the time and temperature are determined based on the particular material being removed from a substrate. Generally, the temperature is in the range of from about ambient or room temperature to about 120° C. and the contact time is from about 2 to 60 minutes.
  • the substrate may then be rinsed in a polar solvent, such as isopropyl alcohol, followed by a deionized water rinse.
  • a polar solvent such as isopropyl alcohol
  • the substrate is then mechanically dried, such as with a spin drier, or nitrogen blow dried.
  • EDTA ethylenediaminetetraacetic acid
  • TAE tetraammonium EDTA
  • DMAC dimethylacetamide
  • DHA N,N-diethylene hydroxylamine
  • Heating was required in some cases to accelerate the solvation of solid components.
  • Ashed-via, unashed wafers and metal wafers with a TiN/Al-Cu/Ti/TiN/Ti or TiN/Al-Cu-Si/Ti stack were processed in these prepared cleaning solutions for
  • the wafers were broken into pieces before and after processing in these different cleaning solutions and subsequently viewed under a FE Hitachi 4500 Scanning
  • Electron Microscope for post ash residue removal in vias and substrate compatibility on metal stacks.
  • EXAMPLE 1 A via opening with a size of 1.2 micron in a silicon oxide dielectric layer was etched through a photoresist patterned opening using a standard silicon oxide plasma etching process. The photoresist was removed by oxygen plasma ashing.
  • Figure 1 A is a micrograph of a scanning electron microscope (SEM) image for a representative substrate of the type used in this example, showing that heavy organometallic etch residue remained on the substrate surface, particularly around the via opening. The substrate was then processed in composition A for 30 minutes at 55° C.
  • Figure IB the resulting SEM photograph, shows that composition A removed all the organometallic residue.
  • composition A does not attack a titanium metallurgy.
  • a sandwich metal thin film substrate of TiN/Al-Cu/Ti/TiN/Ti metallurgy was patterned and etched in a plasma metal etcher.
  • Figure 2A shows that there is organometallic residue left on the metal line surface after photoresist removal by oxygen plasma ashing. The wafer was exposed to composition A at 55° C. for 30 minutes, with substantially complete removal of the organometallic residue and no attack on the titanium metallurgy, as shown in Figure 2B.
  • Example 3 The procedures of Example 3 were repeated with composition C, also at a cleaning temperature of 45 °C.
  • Figures 4 A and 4B show the results obtained. Complete cleaning of the ashed via wafer was obtained, as determined by visual observation of Figure 4A. There was complete control of metal corrosion.
  • Figure 4B shows complete cleaning of the TiN/Al-Cu/Ti/TiN/Ti stack wafer, as shown by the clean appearance of the top TiN layer with no metal corrosion.
  • EXAMPLE 5 The procedures of Example 3 were repeated with composition D but at a cleaning temperature of 65 °C. Figures 5 A, 5B and 5C show the results obtained. A 90 % cleaning of the ashed via wafer was obtained, as determined by visual observation of Figure 5A. There was no metal corrosion. Figure 5B shows almost complete cleaning of residue an unashed via wafer, with some residue only on the bottom of the via. Figure 5C shows complete cleaning of the TiN/Al- Cu/Ti/TiN/Ti stack wafer, with no metal corrosion. EXAMPLE 6 The procedures of Example 5 were repeated with composition E. Figures 6A, 6B and 6C show the results obtained.
  • Figure 6A Surface and sidewall cleaning of the ashed via wafer, with residue only on the bottom of the via was obtained, as determined by visual observation of Figure 6A. There was no metal corrosion.
  • Figure 6B shows complete cleaning of residue on the surface and sidewall of the via of the no-ash wafer, with some residue only on the bottom of the via, with no metal corrosion.
  • Figure 6C shows complete cleaning of the TiN/Al -Cu-Si/Ti stack wafer.
  • Figure 7C shows complete cleaning of the TiN/Al-Cu/Ti/TiN/Ti stack wafer, with no metal corrosion.
  • FIGS. 8A, 8B and 8C show the results obtained. Surface and sidewall cleaning of the ashed via wafer, with residue only on the bottom of the via, was obtained, as determined by visual observation of Figure 8 A. There was no metal corrosion.
  • Figure 8B shows complete cleaning of residue on the surface and sidewall of the via of the no-ash wafer, with residue only on the bottom of the via, with no metal corrosion.
  • Figure 8C shows complete cleaning of the TiN/Al-Cu/Ti/TiN/Ti stack wafer, with either no metal corrosion or just a start of titanium corrosion.
  • Example 9 The procedure of Example 1 was repeated with composition H on three different wafer types. When composition H was mixed, a substantial amount of 10 heat was generated, indicating the in situ formation of tetraammonium EDTA according to the equation:
  • Figures 9A, 9B and 9C show the results obtained.
  • the ashed via wafer was only about 80% cleaned, as determined by visual observation of Figure 9A. Some bulk polymer strips were observed.
  • the TiN/Al-Cu/Ti/TiN/Ti stack wafer was completely cleaned and showed no corrosion of either the aluminum or the titanium layers, as shown in Figure 9B.
  • the Ti/Al-Cu-Si/TiN stack was also completely cleaned with no aluminum or Ti corrosion, as shown in Figure 9C.
  • the improved ethylenediaminetetraacetic acid or a mono- di- tri- or tetraammonium salt thereof based composition and process using such a composition of this invention is suitable for meeting current semiconductor fabrication requirements.
  • the composition and process is suitable for removing photoresist residues and other residues from wafers and other substrates including one or more titanium metal layers without substantial attack on such titanium layers.

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PCT/US1998/005150 1997-04-04 1998-03-17 Ethylenediaminetetraacetic acid or its ammonium salt semiconductor process residue removal composition and process Ceased WO1998045399A1 (en)

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EP98911697A EP0975731B1 (en) 1997-04-04 1998-03-17 Ethylenediaminetetraacetic acid or its ammonium salt semiconductor process residue removal composition and process
JP54278298A JP4138891B2 (ja) 1997-04-04 1998-03-17 エチレンジアミン四酢酸またはそのアンモニウム塩である半導体プロセス残渣除去組成物および方法
KR19997009102A KR100386137B1 (ko) 1997-04-04 1998-03-17 에틸렌디아민사초산 또는 그의 암모늄염 반도체 공정 잔류물 제거 조성물 및 방법
DE69835951T DE69835951T2 (de) 1997-04-04 1998-03-17 Zusammensetzung zur entfernung von rückständen bei der halbleiterherstellung auf basis von ethylendiamintetraessigsäure oder ihrem ammoniumsalz sowie verfahren

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EP0939344A1 (en) * 1998-02-27 1999-09-01 Kanto Kagaku Kabushiki Kaisha Photoresist stripping liquid composition
US6231677B1 (en) 1998-02-27 2001-05-15 Kanto Kagaku Kabushiki Kaisha Photoresist stripping liquid composition
EP0939344B2 (en) † 1998-02-27 2014-07-09 Kanto Kagaku Kabushiki Kaisha Use of a liquid composition for stripping photoresists
EP1063689A4 (en) * 1998-12-09 2001-08-22 Kishimoto Sangyo Co STRIPPING AGENT FOR REMOVING RESIDUE FROM RESERVE
US6534459B1 (en) 1998-12-09 2003-03-18 Kishimoto Sangyo Co., Ltd. Resist residue remover
WO2001098837A1 (en) * 2000-06-19 2001-12-27 Dongjin Semichem Co., Ltd. Photoresist remover composition comprising ammonium fluoride
CN100543124C (zh) * 2003-10-27 2009-09-23 和光纯药工业株式会社 基板用清洗剂及清洗方法
US20120000485A1 (en) * 2003-10-27 2012-01-05 Wako Pure Chemical Industries, Ltd. Cleaning agent for substrate and cleaning method
WO2005040324A1 (ja) * 2003-10-27 2005-05-06 Wako Pure Chemical Industries, Ltd. 基板用洗浄剤及び洗浄方法
US8900371B2 (en) 2003-10-27 2014-12-02 Wako Pure Chemical Industries, Ltd. Cleaning agent for substrate and cleaning method
JP2008519310A (ja) * 2004-11-04 2008-06-05 イーケイシー テクノロジー インコーポレーテッド アルミニウム含有基板に使用するためのポストエッチ洗浄組成物
WO2006052692A3 (en) * 2004-11-04 2007-08-30 Ekc Technology Inc Post etch cleaning composition for use with substrates having aluminum
WO2009071333A3 (de) * 2007-12-06 2009-07-23 Fraunhofer Ges Forschung Textur- und reinigungsmedium zur oberflächenbehandlung von wafern und dessen verwendung
US8900472B2 (en) 2007-12-06 2014-12-02 Fraunhofer-Gesellschaft zur Föerderung der Angewandten Forschung E.V. Texturing and cleaning agent for the surface treatment of wafers and use thereof

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US6492311B2 (en) 2002-12-10
EP0975731B1 (en) 2006-09-20
TW416984B (en) 2001-01-01
SG120055A1 (en) 2006-03-28
DE69835951D1 (de) 2006-11-02
EP0975731A1 (en) 2000-02-02
KR100386137B1 (ko) 2003-06-09
KR20010006024A (ko) 2001-01-15
EP0975731A4 (en) 2001-02-07
DE69835951T2 (de) 2007-06-14
ATE340243T1 (de) 2006-10-15
US20010006936A1 (en) 2001-07-05
JP4138891B2 (ja) 2008-08-27
JP2001526836A (ja) 2001-12-18
US6367486B1 (en) 2002-04-09

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