WO2006113222A2 - Elimination de photoresine a implantation ionique haute dose au moyen de monocouches auto-assemblees dans des systemes de solvants - Google Patents

Elimination de photoresine a implantation ionique haute dose au moyen de monocouches auto-assemblees dans des systemes de solvants Download PDF

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Publication number
WO2006113222A2
WO2006113222A2 PCT/US2006/013430 US2006013430W WO2006113222A2 WO 2006113222 A2 WO2006113222 A2 WO 2006113222A2 US 2006013430 W US2006013430 W US 2006013430W WO 2006113222 A2 WO2006113222 A2 WO 2006113222A2
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sam
containing composition
microelectronic device
silicon
photoresist
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WO2006113222A3 (fr
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Michael B. Korzenski
Pamela M. Visintin
Thomas H. Baum
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Advanced Technology Materials Inc
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Advanced Technology Materials Inc
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Priority to EP06749725A priority Critical patent/EP1877530A4/fr
Priority to CN2006800216226A priority patent/CN101198683B/zh
Priority to JP2008506595A priority patent/JP2008538013A/ja
Priority to US11/552,808 priority patent/US20070251551A1/en
Publication of WO2006113222A2 publication Critical patent/WO2006113222A2/fr
Anticipated expiration legal-status Critical
Publication of WO2006113222A3 publication Critical patent/WO2006113222A3/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P50/00—Etching of wafers, substrates or parts of devices
    • H10P50/20—Dry etching; Plasma etching; Reactive-ion etching
    • H10P50/28—Dry etching; Plasma etching; Reactive-ion etching of insulating materials
    • H10P50/286—Dry etching; Plasma etching; Reactive-ion etching of insulating materials of organic materials
    • H10P50/287—Dry etching; Plasma etching; Reactive-ion etching of insulating materials of organic materials by chemical means
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P32/00—Diffusion of dopants within, into or out of wafers, substrates or parts of devices
    • H10P32/10—Diffusion of dopants within, into or out of semiconductor bodies or layers
    • H10P32/16—Diffusion of dopants within, into or out of semiconductor bodies or layers between a solid phase and a liquid phase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/162—Organic compounds containing Si
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43—Solvents
    • 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
    • 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
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • 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
    • 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
    • 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
    • C11D2111/22—Electronic devices, e.g. PCBs or semiconductors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P30/00—Ion implantation into wafers, substrates or parts of devices
    • H10P30/20—Ion implantation into wafers, substrates or parts of devices into semiconductor materials, e.g. for doping
    • H10P30/22—Ion implantation into wafers, substrates or parts of devices into semiconductor materials, e.g. for doping using masks

Definitions

  • the present invention relates to self-assembled monolayer (SAM)-containing compositions useful for the removal of bulk and hardened photoresist from the surface of microelectronic devices, and methods of using said compositions for removal of same.
  • SAM self-assembled monolayer
  • ion implantation has been extensively employed during front-end-of-line (FEOL) processing to accurately control impurity distributions in the microelectronic device and to add dopant atoms, e.g., As, B and P, to the exposed device layers.
  • the concentration and depth of the dopant impurity is controlled by varying the dose of the dopant, the acceleration energy, and the ion current.
  • the ion-implanted photoresist layer Prior to subsequent processing, the ion-implanted photoresist layer must be removed.
  • the removal of the ion-implanted photoresist and other contaminants is usually performed by a plasma etch method followed by a multi-step wet strip process, typically using aqueous-based etchant formulations to remove photoresist, post-etch residue and other contaminants.
  • Wet strip treatments in the art generally involve the use of strong acids, bases, solvents, and oxidizing agents.
  • wet strip treatments also etch the underlying silicon-containing layers, such as the substrate and gate oxide, and/or increase the gate oxide thickness.
  • aqueous-based etchant formulations of the prior art.
  • Water has a high surface tension which limits or prevents access to the smaller image nodes with high aspect ratios, and therefore, removing the residues in the crevices or grooves becomes more difficult.
  • aqueous-based etchant formulations often leave previously dissolved solutes behind in the trenches or vias upon evaporative drying, which inhibit conduction and reduce device yield.
  • underlying porous low-k dielectric materials do not have sufficient mechanical strength to withstand the capillary stress of high surface tension liquids such as water, resulting in pattern collapse of the structures.
  • Aqueous etchant formulations can also strongly alter important material properties of the low-k materials, including dielectric constant, mechanical strength, moisture uptake, coefficient of thermal expansion, and adhesion to different substrates.
  • the improved composition shall effectively remove bulk and hardened photoresist in a one-step or multi-step process, without the need for a plasma etch step and without substantially over-etching the underlying silicon- containing layer (s).
  • the present invention relates to self-assembled monolayer (SAM)-containing compositions useful for the removal of bulk and hardened photoresist from the surface of microelectronic devices, methods of making and methods of using said compositions for removal of same, and improved microelectronic devices made using the same.
  • the invention relates to a self assembled monolayer (SAM)- containing composition, comprising at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant, wherein said SAM-containing composition is suitable for removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon.
  • the present invention relates to a kit comprising, in one or more containers, SAM-containing composition reagents, wherein the SAM-containing composition comprises at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant, and wherein the kit is adapted to form a SAM-containing composition suitable for removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon.
  • the present invention relates to a method of removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon, said method comprising contacting the microelectronic device with a SAM-containing composition for sufficient time and under sufficient contacting conditions to at least partially remove said photoresist material from the microelectronic device, wherein the SAM-containing composition includes at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant.
  • the present invention relates to a method of removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon, said method comprising contacting the microelectronic device with a SAM- containing composition for sufficient time to at least partially passivate a silicon-containing layer underlying the photoresist material, and contacting the microelectronic device with an etchant-containing removal composition to at least partially remove said photoresist material from the microelectronic device, wherein the SAM-containing composition comprises a non- halide containing SAM component.
  • the present invention relates to a method of removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon, said method comprising contacting the microelectronic device with a SAM-containing composition for sufficient time to at least partially remove said photoresist material from the microelectronic device, wherein the SAM-containing composition is devoid of an etchant component.
  • the present invention relates to a method of manufacturing a microelectronic device, said method comprising contacting the microelectronic device with an SAM-containing composition for sufficient time to at least partially remove bulk and hardened photoresist material from the microelectronic device having said photoresist material thereon, wherein the SAM-containing composition includes at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant, and optionally incorporating said cleaned microelectronic device into a product.
  • Figure 2 illustrates the cleaning efficiency of a SAM-containing composition of the present invention as a function of temperature for four different microelectronic device layers including a bulk blanketed photoresist layer (Bulk PR), a blanketed ion-implanted photoresist layer (Crust), a bulk patterned photoresist layer (Patterned PR) and a patterned ion-implanted photoresist layer (Patterned Crust).
  • Bulk PR blanketed photoresist layer
  • Crust blanketed ion-implanted photoresist layer
  • Patterned PR a blanketed ion-implanted photoresist layer
  • Patterned Crust patterned ion-implanted photoresist layer
  • Figures 3A-3C are atomic force micrographs of the microelectronic device surfaces following contact of a SAM-containing composition including ClSiMe 3 (Figure 3A), Cl 2 SiMe 2 ( Figure 3B), and Cl 3 SiMe ( Figure 3C), in 2 mmol Et 3 N in 10 mL of toluene, with the device surface at a contacting temperature of 70 0 C for 30 min.
  • Figures 4A-4C are optical microscope images ( Figure 4A) and scanning electron microscopic (SEM) images ( Figures 4B-4C) of densely patterned, ion implanted photoresist on a microelectronic device surface.
  • Figures 5A-5C are optical microscope images of the microelectronic device surfaces following contact of a SAM-containing composition including ClSiMe 3 (Figure 5A), Cl 2 SiMe 2 ( Figure 5B), and Cl 3 SiMe ( Figure 5C), at 7O 0 C for 30 min.
  • Figure 6 illustrates the removal efficiency of a SAM-containing composition of the present invention as a function of SAM functionality for the four different microelectronic device layers including a bulk blanketed photoresist layer (Bulk PR), a blanketed ion-implanted photoresist layer (Crust), a bulk patterned photoresist layer (Patterned PR) and a patterned ion- implanted photoresist layer (Patterned Crust).
  • Figures 7A-7C are optical microscope images of the control surface (Fig. 7A), the surface following cleaning and passivation using a SAM-containing composition of the invention (Fig. 7B), and the surface following depassivation according to the invention (Fig. 7C).
  • Figures 8A-8E are scanning electron micrographs of the control surface (Fig. 8A), the surface following cleaning and passivation using a SAM-containing composition of the invention (Fig. 8B), the surface following depassivation at a 90° angle view (Fig. 8C) and a 60° angle view (Fig. 8D), and a purposely over-etched surface following depassivation (Fig. 8E).
  • the present invention is based on the discovery of self-assembled monolayer (SAM)- containing compositions that are highly efficacious for the removal of bulk and hardened photoresist from the surface of microelectronic devices, while maintaining the integrity of the underlying silicon-containing layer(s).
  • SAM self-assembled monolayer
  • Hardened photoresist corresponds to the non-carbonized photoresist on the microelectronic device surface, specifically adjacent and below the hardened photoresist crust.
  • Hardened photoresist includes, but is not limited to, photoresist that has been plasma etched, e.g., during back-end-of-line (BEOL) dual-damascene processing of integrated circuits, ion implanted, e.g., during front-end-of-line (FEOL) processing to implant dopant species in the appropriate layers of the semiconductor wafer, and/or any other methodology whereby a carbonized or highly cross-linked crust forms on the exposed surface of the bulk photoresist.
  • BEOL back-end-of-line
  • FEOL front-end-of-line
  • underlying silicon-containing layer corresponds to the layer(s) immediately below the bulk and/or the hardened photoresist including: silicon; silicon oxide, including gate oxides (e.g., thermally or chemically grown SiO 2 ) and TEOS; silicon nitride; and low-k silicon-containing materials.
  • low-k silicon-containing material corresponds to any material used as a dielectric material in a layered microelectronic device, wherein the material has a dielectric constant less than about 3.5.
  • the low-k dielectric materials include low-polarity materials such as silicon-containing organic polymers, silicon-containing hybrid organic/inorganic materials, organosilicate glass (OSG), TEOS, fluorinated silicate glass (FSG), silicon dioxide, and carbon-doped oxide (CDO) glass. It is to be appreciated that the low-k dielectric materials may have varying densities and varying porosities.
  • Microelectronic device corresponds to semiconductor substrates, flat panel displays, and microelectromechanical systems (MEMS), manufactured for use in microelectronic, integrated circuit, or computer chip applications. It is to be understood that the term “microelectronic device” is not meant to be limiting in any way and includes any substrate that will eventually become a microelectronic device or microelectronic assembly.
  • MEMS microelectromechanical systems
  • substantially over-etching corresponds to greater than about 10% removal, more preferably greater than about 5% removal, and most preferably greater than about 2% removal, of the adjacent underlying silicon-containing layer(s) following contact, according to the process of the present invention, of the SAM-containing compositions of the invention with the microelectronic device having said underlying layer(s). In other words, most preferably no more than 2% of the underlying silicon-containing layer(s) are etched using the compositions of the present invention for the prescribed times. [0029] As used herein, "about” is intended to correspond to ⁇ 5 % of the stated value.
  • suitable for removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon corresponds to at least partial removal of said photoresist material from the microelectronic device.
  • at least 90 % of the photoresist material is removed from the microelectronic device using the compositions of the invention, more preferably, at least 95%, and most preferably at least 99% of the photoresist material, is removed.
  • Dispos fluid corresponds to a supercritical fluid or a subcritical fluid.
  • supercritical fluid is used herein to denote a material which is under conditions of not lower than a critical temperature, T c , and not less than a critical pressure, P 0 , in a pressure- temperature diagram of an intended compound.
  • the preferred supercritical fluid employed in the present invention is CO 2 , which may be used alone or in an admixture with another additive such as Ar, NH 3 , N 2 , CH 4 , C 2 H 4 , CHF 3 , C 2 H 6 , n-C 3 H 8 , H 2 O, N 2 O and the like.
  • subcritical fluid describes a solvent in the subcritical state, i.e., below the critical temperature and/or below the critical pressure associated with that particular solvent.
  • the subcritical fluid is a high pressure liquid of varying density.
  • the SAM-containing compositions of the present invention must possess good metal-containing material compatibility, e.g., a low etch rate on the metal-containing material.
  • Metal-containing materials of interest include, but are not limited to, copper, tungsten, cobalt, aluminum, tantalum, titanium and ruthenium and suicides and nitrides thereof.
  • Self assembled monolayers (SAMs) are known to passivate various surfaces, including, but not limited to, metals (e.g., copper, gold, etc), and oxides of titanium, hafnium, silicon, and aluminum.
  • SAMs include silanes having at least one leaving group, e.g., a halide, said silane readily forming a covalent bond at an oxygen group on a silicon-containing surface (i.e., via a silylation reaction).
  • the silanes themselves may further include covalently bonded inert molecules, such as polyethylene glycol (PEG), whereby following attachment with the silicon- containing surface, the PEG-silane can block other molecules from binding with said surface.
  • PEG-silane SAMs are popular because they are thin (i.e., non-bulky) and hydrophilic, and linkage of the PEG molecule with the silicon-containing surface results in a non-sticky, water- like layer.
  • alkylchlorosilanes may be used to form a hydrophobic surface, if necessary.
  • compositions of the invention may be embodied in a wide variety of specific formulations, as hereinafter more fully described.
  • compositions wherein specific components of the composition are discussed in reference to weight percentage ranges including a zero lower limit, it will be understood that such components may be present or absent in various specific embodiments of the composition, and that in instances where such components are present, they may be present at concentrations as low as 0.01 weight percent, based on the total weight of the composition in which such components are employed.
  • the invention relates to a liquid SAM-containing composition useful in removing bulk and hardened photoresist from a microelectronic device.
  • the liquid composition according to one embodiment comprises at least one SAM component, optionally at least one solvent, optionally at least one catalyst, and optionally at least one surfactant.
  • the liquid composition according to another embodiment comprises at least one SAM component, at least one catalyst, optionally at least one solvent, and optionally at least one surfactant.
  • the liquid composition according to yet another embodiment comprises at least one SAM component, at least one solvent, at least one catalyst, and optionally at least one surfactant.
  • the solvent may act concurrently as the catalyst.
  • the invention relates to a liquid SAM-containing composition useful in removing bulk and hardened photoresist from a microelectronic device, wherein the catalyst concurrently acts as the solvent.
  • the liquid composition according to this embodiment comprises at least one catalyst, at least one SAM component, and optionally at least one surfactant present in the following ranges, based on the total weight of the composition: component of % by weight catalyst(s) about 85.0% to about 99.99%
  • Surfactant(s) 0% to about 10.0%
  • the invention relates to a liquid SAM- containing composition useful in removing bulk and hardened photoresist from a microelectronic device.
  • the liquid composition according to this embodiment comprises at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant present in the following ranges, based on the total weight of the composition: component of % by weight solvent(s) about 75.0% to about 99.98%
  • Surfactant(s) 0% to about 10.0%
  • the range of mole ratios of SAM(s) relative to catalyst(s) in the liquid SAM-containing composition is about 1:10 to about 5:1, more preferably about 1:5 to about 1:1; the range of mole ratios of SAM(s) relative to liquid solvent(s) is about 1:200 to about 1:50, more preferably about 1:125 to about 1:75; and the range of mole ratios of SAM(s) relative to surfactant(s) (when present) is about 1:10 to about 5:1.
  • the liquid SAM-containing composition may comprise, consist of, or consist essentially of at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant.
  • Solvent species useful in the compositions of the invention may be non-polar or polar in nature.
  • Illustrative non-polar species include, but are not limited to, toluene, decane, dodecane, octane, pentane, hexane, tetrahydrofuran (THF) and carbon dioxide (subcritical or supercritical).
  • Illustrative polar species include methanol, ethanol, isopropanol, N- methylpyrrolidinone, N-octylpyrrolidinone, N-phenylpyrrolidinone, dimethylsulfoxide (DMSO), sulfolane, ethyl lactate, ethyl acetate, toluene, acetone, methyl carbitol, butyl carbitol, hexyl carbitol, monoethanolamine, butyrol lactone, diglycol amine, alkyl ammonium fluoride, ⁇ -butyrolactone, butylene carbonate, ethylene carbonate, and propylene carbonate and mixtures thereof.
  • DMSO dimethylsulfoxide
  • the solvent comprises a non-polar species.
  • Toluene is especially preferred.
  • the SAM component may include alkoxyhalosilanes including (RO) 3 SiX, (RO) 2 SiX 2 , (RO)SiX 3 , where X may be the same as or different from one another and is selected from the group consisting of F, Cl, Br or I, and RO may be the same as or different from one another and is selected from the group consisting of straight-chained or branched Q- C 20 alkoxy species such as methoxy, ethoxy, propoxy, etc., or combinations thereof.
  • the SAM component includes alkylhalosilanes of the nature (R) 3 SiX, (R) 2 SiX 2 , (R)SiX 3 , where X may be the same as or different from one another and is selected from the group consisting of F, Cl, Br or I, and R may be the same as or different from one another and is selected from the group consisting of straight-chained, branched or cyclic Ci-C 20 alkyl species such as methyl, ethyl, propyl, butyl, octyl, decyl, dodecyl, etc., or combinations thereof. Fluorinated alkyl and alkoxy derivatives may also be used.
  • the catalyst is included in the composition of the invention to initiate the silylation reaction and speed up the passivation of the underlying silicon-containing layer(s).
  • the catalysts include amines such as trimethylamine, triethylamine, butylamine, pyridine, and any other nucleophilic compound that aids in the removal of a halogen leaving group from the SAM component. It is thought that the amine catalyst promotes an in situ silylation reaction, whereby the SAM silane covalently attaches to oxygen atoms on the underlying silicon-containing layer(s), with the simultaneous generation of a protonated leaving group, e.g., HX.
  • the underlying silicon- containing layer is passivated by the covalently bound silane, while the generated protonated leaving group is available for removal of the hardened photoresist material.
  • the solvent may act concurrently as the catalyst.
  • the liquid SAM-containing compositions of the invention may further include a surfactant to assist in the removal of the resist from the surface of the microelectronic device.
  • Illustrative surfactants include, but are not limited to, fluoroalkyl surfactants, polyethylene glycols, polypropylene glycols, polyethylene or polypropylene glycol ethers, carboxylic acid salts, dodecylbenzenesulfonic acid or salts thereof, polyacrylate polymers, dinonylphenyl polyoxyethylene, silicone or modified silicone polymers, acetylenic diols or modified acetylenic diols, alkylammonium or modified alkylammonium salts, as well as combinations of the foregoing surfactants.
  • fluoroalkyl surfactants polyethylene glycols, polypropylene glycols, polyethylene or polypropylene glycol ethers, carboxylic acid salts, dodecylbenzenesulfonic acid or salts thereof, polyacrylate polymers, dinonylphenyl polyoxyethylene, silicone or modified silicone polymers, acetylenic diols or modified
  • the liquid SAM-containing composition includes less than about 1 wt. % water, more preferably less than about 0.5 wt. % water, and most preferably less than about 0.25 wt. % water, based on the total weight of the composition.
  • the at least one SAM component does not undergo substantial polymerization at the microelectronic device surface.
  • preferably less than 5 wt. % of the SAM component polymerizes at the microelectronic device surface, more preferably less than 2 wt. %, even more preferably less than 1 wt. %, and most preferably less than 0.1 wt. % of the SAM component polymerizes at the microelectronic device surface.
  • the specific proportions and amounts of at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant, in relation to each other may be suitably varied to provide the desired cleaning and passivating action of the liquid SAM-containing composition for the bulk and hardened photoresist to be removed from the microelectronic device.
  • Such specific proportions and amounts are readily determinable by simple experiment within the skill of the art without undue effort.
  • the SAM- containing component(s) and the catalyst(s) are present in an amount effective to remove bulk and hardened photoresist material from a microelectronic device having said material thereon.
  • the liquid SAM-containing composition of the present invention may be used to remove hardened photoresist, e.g., BEOL hardened photoresist, bottom anti-reflective coating (BARC) material, post-CMP residue, BARC residue and/or post-ash/post-etch photoresist, while simultaneously passivating the underlying silicon- containing layer(s) or any other hydrophilic surface having hydroxyl-terminated groups in need of passivation.
  • the liquid SAM-containing compositions of the present invention may be used to remove contaminating materials from photomask materials for re-use thereof.
  • the liquid SAM-containing compositions of the invention may optionally be formulated with additional components to further enhance the passivation and removal capability of the composition, or to otherwise improve the character of the composition, i.e., provide metal passivation. Accordingly, the composition may be formulated with stabilizers, complexing agents, passivators, e.g., Cu passivating agents, and/or corrosion inhibitors.
  • the liquid SAM-containing compositions of the invention are easily formulated by the mixture of solvent(s), catalyst(s), SAM component(s), and optional surfactant(s) with gentle agitation.
  • the solvent(s), catalyst(s), SAM component(s), and optional surfactant(s) may be readily formulated as single-package fo ⁇ nulations or multi-part fo ⁇ nulations that are mixed at the point of use.
  • the individual parts of the multi-part formulation may be mixed at the tool or in a storage tank upstream of the tool.
  • concentrations of the single-package formulation or the individual parts of the multi-part formulations may be widely varied in specific multiples, i.e., more dilute or more concentrated, in the broad practice of the invention, and it will be appreciated that the liquid SAM-containing compositions of the invention can variously and alternatively comprise, consist or consist essentially of any combination of ingredients consistent with the disclosure herein.
  • kits including, in one or more containers, one or more components adapted to form the compositions of the invention.
  • the kit includes, in one or more containers, at least one solvent, at least one SAM component, and optionally at least one surfactant for combining with the at least one catalyst at the fab.
  • the kit includes, in one or more containers, at least one SAM component, and optionally at least one surfactant for combining with the at least one solvent and the at least one catalyst at the fab.
  • the kit includes in one container at least one SAM component in solvent and in another container at least one catalyst in solvent for combining at the fab. .
  • the containers of the kit may be NOWPak® containers (Advanced Technology Materials, Inc., Danbury, Conn., USA).
  • the invention relates to a liquid SAM-containing composition useful in removing bulk and hardened photoresist from a microelectronic device, wherein the liquid SAM-containing composition includes at least one solvent, at least one catalyst, at least one SAM component, optionally at least one surfactant, and photoresist residue material, wherein the photoresist is bulk and/or hardened photoresist.
  • the residue material may be dissolved and/or suspended in the liquid SAM-containing composition of the invention.
  • the photoresist residue material includes an ion selected from the group consisting of boron ions, arsenic ions, phosphorus ions, indium ions, and antimony ions.
  • the invention relates to dense SAM-containing compositions including dense fluids, e.g., supercritical fluids (SCF), as the primary solvent system.
  • dense fluids e.g., supercritical fluids (SCF)
  • SCCO 2 supercritical carbon dioxide
  • SCCO 2 is an attractive reagent for removal of microelectronic device process contaminants, since SCCO 2 has the characteristics of both a liquid and a gas. Like a gas, it diffuses rapidly, has low viscosity, near-zero surface tension, and penetrates easily into deep trenches and vias. Like a liquid, it has bulk flow capability as a "wash" medium.
  • the dense SAM-containing composition comprises SCCO 2 and the liquid SAM-containing composition, i.e., a SAM-containing concentrate, in the following ranges, based on the total weight of the composition:
  • SCCO 2 about 95.0% to about 99.99% liquid SAM-containing composition about 0.01% to about 10.0%
  • liquid SAM-containing composition comprises about 75.0% to about 90.0% co- solvent, about 0.01% to about 10.0% SAM component, about 0.01% to about 10.0% catalyst and optionally 0 to about 10.0% surfactant, wherein the co-solvent(s), SAM-component(s), catalyst(s) and optional surfactant(s) contemplated include the aforementioned species.
  • the range of mole ratios of liquid SAM-containing composition relative to SCCO 2 in the dense SAM-containing composition is about 1:200 to about 1:4, more preferably about 1:100 to about 1:6.
  • the dense SAM-containing composition may comprise, consist of, or consist essentially of SCCO 2 and the liquid SAM-containing composition, i.e., at least one additional solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant.
  • the specific proportions and amounts of SCCO 2 and liquid SAM-containing composition, in relation to each other, may be suitably varied to provide the desired removal action of the dense SAM-containing composition for the bulk and hardened photoresist and/or processing equipment, as readily determinable within the skill of the art without undue effort.
  • the liquid SAM-containing composition may be at least partially dissolved and/or suspended within the dense fluid of the dense SAM-containing composition.
  • the invention relates to a dense SAM-containing composition useful in removing bulk and hardened photoresist from a microelectronic device, wherein the dense SAM-containing composition includes SCCO 2 , at least one solvent, at least one catalyst, at least one SAM component, optionally at least one surfactant, and photoresist residue material, wherein the photoresist is bulk and/or hardened photoresist.
  • the residue material may be dissolved and/or suspended in the dense SAM-containing composition of the invention.
  • the photoresist residue material includes an ion selected from the group consisting of boron ions, arsenic ions, phosphorus ions, indium ions, and antimony ions.
  • the dense SAM-containing composition of the present invention may be used to remove hardened photoresist, e.g., BEOL hardened photoresist, bottom anti-reflective coating (BARC) material, post-CMP residue, BARC residue and/or post-ash/post-etch photoresist, while simultaneously passivating the underlying silicon- containing layer(s) or any other hydrophilic surface having hydroxyl-terminated groups in need of passivation.
  • the dense SAM-containing compositions of the present invention may be used to remove contaminating materials from photomask materials for re-use thereof.
  • the invention relates to methods of removal of bulk and hardened photoresist from a microelectronic device using the SAM-containing compositions described herein. For example, trench and via structures on the patterned devices may be cleaned while maintaining the structural integrity of the underlying silicon-containing layers using SAM passivation. It should be appreciated by one skilled in the art that the SAM-containing compositions may be used in a one-step or multi-step removal process.
  • the SAM-containing compositions of the present invention overcome the disadvantages of the prior art removal techniques by reversibly passivating the underlying silicon-containing layer(s), while simultaneously removing the bulk and hardened photoresist deposited thereon.
  • liquid SAM-containing compositions of the present invention are readily formulated by simple mixing of ingredients, e.g., in a mixing vessel or the cleaning vessel under gentle agitation.
  • the dense SAM-containing compositions are readily formulated by static or dynamic mixing at the appropriate temperature and pressure.
  • the liquid SAM-containing composition is applied in any suitable manner to the microelectronic device having photoresist material thereon, e.g., by spraying the composition on the surface of the device, by dipping (in a volume of the composition) of the device including the photoresist material, by contacting the device with another material, e.g., a pad, or fibrous sorbent applicator element, that is saturated with the composition, by contacting the device including the photoresist material with a circulating composition, or by any other suitable means, manner or technique, by which the liquid SAM- containing composition is brought into contact with the photoresist material on the microelectronic device.
  • the passivation and removal application may be static or dynamic, as readily determined by one skilled in the art.
  • the liquid SAM-containing composition typically is contacted with the device surface for a time of from about 1 to about 60 minutes, the preferred time being dependent on the dopant ion dose and the implant energy employed during ion implantation, wherein the higher the dopant ion dose and/or implant energy, the longer the contacting time required.
  • temperature is in a range of from about 2O 0 C to about 8O 0 C, preferably about 3O 0 C to about 8O 0 C, most preferably about 7O 0 C.
  • contacting times and temperatures are illustrative, and any other suitable time and temperature conditions may be employed that are efficacious to at least partially remove the photoresist material from the device surface, within the broad practice of the invention.
  • "at least partial removal” corresponds to at least 90% removal of bulk and hardened photoresist, preferably at least 95% removal. Most preferably, at least 99% of said bulk and hardened photoresist material is removed using the compositions of the present invention.
  • the microelectronic device may be thoroughly rinsed with copious amounts of ethanol and/or THF to remove any residual chemical additives.
  • the SAM-containing compositions of the invention selectively remove 100% of highly doped (with 2 x 10 15 As ions cm “2 ) photoresist (500-700 nm thick) having a hardened, cross-linked carbonized crust ranging from 30-70 nm in thickness. Importantly, the hardened crust is removed without substantially over-etching the underlying silicon-containing layer(s).
  • the microelectronic device surface having the photoresist thereon is contacted with the dense SAM-containing composition, at suitable elevated pressures, e.g., in a pressurized contacting chamber to which the dense SAM-containing composition is supplied at suitable volumetric rate and amount to effect the desired contacting operation, for at least partial removal of the photoresist from the microelectronic device surface.
  • the chamber may be a batch or single wafer chamber, for continuous, pulsed or static cleaning.
  • the passivation and removal of the hardened photoresist by the dense SAM-containing composition may be enhanced by use of elevated temperature and/or pressure conditions during contacting of the photoresist with the dense SAM-containing composition.
  • the appropriate dense SAM-containing composition may be employed to contact a microelectronic device surface having photoresist thereon at a pressure in a range of from about 1,500 to about 4,500 psi for sufficient time to effect the desired removal of the photoresist, e.g., for a contacting time in a range of from about 5 minutes to about 30 minutes and a temperature of from about 4O 0 C to about 75 0 C, although greater or lesser contacting durations and temperatures may be advantageously employed in the broad practice of the present invention.
  • the removal process using the dense SAM-containing composition may include a static soak, a dynamic cleaning mode, or sequential processing steps including dynamic flow of the dense SAM-containing composition over the microelectronic device surface, followed by a static soak of the device in the dense SAM-containing composition, with the respective dynamic flow and static soak steps being carried out alternatingly and repetitively, in a cycle of such alternating steps.
  • a “dynamic” contacting mode involves continuous flow of the composition over the device surface, to maximize the mass transfer gradient and effect complete removal of the resist from the surface.
  • a “static soak” contacting mode involves contacting the device surface with a static volume of the composition, and maintaining contact therewith for a continued (soaking) period of time. 2
  • the device thereafter preferably is washed with rinsing solution, for example, aliquots of SCF/co-solvent solution, e.g., SCCO 2 /methanol (80%/20%) solution, and pure SCF, to remove any residual precipitated chemical additives from the region of the device surface in which resist removal has been effected.
  • rinsing solution for example, aliquots of SCF/co-solvent solution, e.g., SCCO 2 /methanol (80%/20%) solution, and pure SCF
  • Another aspect of the invention relates to methods of removal of bulk and hardened photoresist from a microelectronic device, said method including passivation of the underlying silicon-containing layer(s) on the microelectronic device surface using non-halide containing SAM component, e.g., hexamethyldisilazane (HMDS), and removing the bulk and hardened photoresist from the microelectronic device using an etchant- containing removal composition.
  • non-halide containing SAM component e.g., hexamethyldisilazane (HMDS)
  • Suitable etchant-containing removal compositions include without limitation, hydrogen fluoride (HF), ammonium fluoride (NH 4 F), alkyl hydrogen fluoride (NRH 3 F), dialkylammonium hydrogen fluoride (NR 2 H 2 F), trialkylammonium hydrogen fluoride (NR 3 HF), rrialkylammonium trihydrogen fluoride (NR 3 (3HF)), tetraalkylammonium fluoride (NR 4 F), pyridine-HF complex, pyridine/HCl complex, pyridine/HBr complex, triethylamine/HF complex, triethylamine/HCl complex, monoethanolamine/HF complex, triethanolamine/HF complex, triethylamine/formic acid complex ,and xenon difluoride (XeF 2 ), wherein each R in the aforementioned R-substituted species is independently selected from C 1 -C 8 alkyl and C 6 -Ci 0 aryl. Additional species are disclosed in co
  • the invention relates to a method of removing bulk and hardened photoresist material from a microelectronic device having said photoresist material thereon, said method comprising contacting the microelectronic device with a SAM-containing composition for sufficient time to at least partially remove said photoresist material from the microelectronic device, with the provision that the SAM-containing composition is devoid of an etchant component selected from the group consisting of hydrogen fluoride, ammonium fluoride, ammonium bifluorides and other well-known fluoride etchant species.
  • an etchant component selected from the group consisting of hydrogen fluoride, ammonium fluoride, ammonium bifluorides and other well-known fluoride etchant species.
  • a further aspect of the invention includes the removal of the SAM passivating layer from the surface of the microelectronic device subsequent to the removal of the photoresist material therefrom, referred to herein as "depassivation.”
  • depassivation the removal of the SAM passivating layer from the surface of the microelectronic device subsequent to the removal of the photoresist material therefrom.
  • dilute inorganic acids including halide ions, such as HCl and HF, are preferred under optimized process conditions.
  • halide ions such as HCl and HF
  • the halide ions will readily attack a passivating Si-O-Si bond at the SAM- device surface interface and thus "depassivate" the device surface.
  • special care should be taken to minimize over-etching of the silicon-containing layer(s) on the device surface.
  • the depassivating solution may include about 0.01 wt% to about 2 wt. % dilute inorganic acid/amine complex in a solvent to depassivate the device surface with only slight fluorination and over-etching of the underlying silicon-containing layers.
  • Dilute inorganic acid/amine complexes contemplated herein include pyridine/HF complex, pyridine/HCl complex, pyridine/HBr complex, triethylamine/HF complex, triethylamine/HCl complex, and triethylamine/formic acid complex, and combinations thereof with peroxides, concentrated HCl, ammonium hydroxide, and mixtures thereof.
  • Solvents contemplated herein for the depassivating solution include, but are not limited to, DMSO, methanol, and ethyl acetate.
  • Yet another aspect of the invention relates to the improved microelectronic devices made according to the methods of the invention and to products containing such microelectronic devices.
  • a still further aspect of the invention relates to methods of manufacturing an article comprising a microelectronic device, said method comprising contacting the microelectronic device with a SAM-containing composition for sufficient time to at least partially remove bulk and hardened photoresist material from the microelectronic device having said photoresist material thereon, and incorporating said microelectronic device into said article, wherein the SAM-containing composition includes at least one solvent, at least one catalyst, at least one SAM component, and optionally at least one surfactant.
  • the SAM-containing composition may further include a dense fluid.
  • AFM Atomic Force Microscopy
  • surface energy measurements were performed before and after contact of a sample device surface with the SAM-containing compositions of the invention to determine the extent of removal of hardened photoresist as well as monolayer formation on the surface of said device.
  • the sample device surfaces included wafers consisting of (from top to bottom) an ion-implanted photoresist layer (2 x 10 15 As ions cm “2 ; 10 keV implant energy), a bulk photoresist layer, a silicon-containing gate oxide 2
  • Table 1 Processing as a function of time using a SAM-containing composition including 1 , mmol Cl 3 SiMe and 2 mmol Et 3 N in 10 mL of toluene, and a contacting temperature of 7O 0 C.
  • Table 2 Processing as a function of temperature using a SAM-containing composition including 1 mmol Cl 3 SiMe and 2 mmol Et 3 N in 10 mL of toluene, and a contacting time of 30 min.
  • Table 3 Processing as a function of SAM functionalities using a SAM-containing composition including 1 mmol of the listed SAM and 2 mmol Et 3 N in 10 mL of toluene, at a contacting temperature of 70 0 C for a contacting time of 30 min.
  • FIGs 4A-4C show the optical (Fig. 4A) and scanning electron microscopic (SEM) images of sample device surfaces including a layer of densely patterned, highly doped (2 x 10 15 As ions cm “2 ; 10 keV implant energy) photoresist consisting of a region of parallel lines.
  • the ⁇ 30 nm thick hardened crust can be clearly seen in the 90 degree angle view image (Fig. 4C).
  • the cleaning efficiency of the crust as a function of chloride substitution on the SAM component is illustrated in Figure 5A (ClSiMe 3 ), Figure 5B (Cl 2 SiMe 2 ), and Figure 5C (Cl 3 SiMe).
  • 5A-5C illustrate that as the number of chloride leaving groups on the SAM component increases, the amount of hardened photoresist removed also increases, hi fact, greater than 90% removal of the four different microelectronic device layers is achievable using the Cl 3 SiMe-containing composition (see Figure 6). It is thought that the increase in crust removal is the result of an increase in HCl generated when the SAM-containing composition is applied to the device surface.
  • a further aspect of the invention includes the removal of the passivating layer from the surface of the microelectronic device, or "depassivation.”
  • Figure 7B is an optical image of the device surface of Fig. 7A following application at 70 0 C for 30 min of a SAM-containing composition including Cl 3 SiMe.
  • Figure 7C is an optical image of the device surface of Fig. 7B following depassivation at 50 0 C for 2 min using NEt 3 :HF (1:3 mole ratio) in DMSO composition.
  • depassivation process should be optimized in order to eliminate fiuorination and/or over-etching of the underlying silicon-containing layer(s). For example, depassivation may be performed in 30 second intervals for SAM removal from thermal oxide- containing device structures and 20 second intervals for SAM removal from TEOS-based device structures.
  • Figures 8A-8E provide another illustration of the passivation and cleaning results, as well as depassivation following removal of the hardened photoresist.
  • Figure 8A is a SEM of a device surface including a densely patterned, highly doped (2 x 10 15 As ions cm “2 ; 10 keV implant energy) photoresist layer prior to processing.
  • Figure 8B is a SEM of the densely patterned surface of Fig. 8 A following application at 70 0 C for 30 min of a SAM-containing composition including Cl 3 SiMe, illustrating the successful and efficient removal (and passivation) of the hardened photoresist.
  • Figures 8C and 8D are SEMs of the device surface of Fig.

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Abstract

L'invention concerne un procédé et des compositions contenant des monocouches auto-assemblées (SAM) servant à éliminer un matériau photorésine en vrac et durcie de dispositifs micro-électroniques. Les compositions selon l'invention contiennent au moins un solvant, au moins un catalyseur, au moins un composant SAM et facultativement un tensioactif. Ces compositions permettent d'éliminer efficacement le matériau photorésine durcie tout en passivant simultanément la/les couche(s) sous-jacente(s) contenant du silicium au cours d'un processus en une seule étape.
PCT/US2006/013430 2005-04-15 2006-04-10 Elimination de photoresine a implantation ionique haute dose au moyen de monocouches auto-assemblees dans des systemes de solvants Ceased WO2006113222A2 (fr)

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EP06749725A EP1877530A4 (fr) 2005-04-15 2006-04-10 Elimination de photoresine a implantation ionique haute dose au moyen de monocouches auto-assemblees dans des systemes de solvants
CN2006800216226A CN101198683B (zh) 2005-04-15 2006-04-10 使用溶剂体系内的自组装单层除去高剂量离子注入光致抗蚀剂
JP2008506595A JP2008538013A (ja) 2005-04-15 2006-04-10 溶媒系中の自己組織化単分子膜を用いた高線量イオン注入フォトレジストの除去
US11/552,808 US20070251551A1 (en) 2005-04-15 2006-10-25 Removal of high-dose ion-implanted photoresist using self-assembled monolayers in solvent systems

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