WO2006057782A1 - Silicon containing tarc/barrier layer - Google Patents

Silicon containing tarc/barrier layer Download PDF

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Publication number
WO2006057782A1
WO2006057782A1 PCT/US2005/039719 US2005039719W WO2006057782A1 WO 2006057782 A1 WO2006057782 A1 WO 2006057782A1 US 2005039719 W US2005039719 W US 2005039719W WO 2006057782 A1 WO2006057782 A1 WO 2006057782A1
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WIPO (PCT)
Prior art keywords
barrier layer
group
antireflective coating
methyl
layer material
Prior art date
Application number
PCT/US2005/039719
Other languages
French (fr)
Original Assignee
International Business Machines Corporation
Huang, Wu-Song, S.
Burns, Sean, D.
Varanasi, Pushkara, Rao
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Publication date
Application filed by International Business Machines Corporation, Huang, Wu-Song, S., Burns, Sean, D., Varanasi, Pushkara, Rao filed Critical International Business Machines Corporation
Priority to CN2005800376305A priority Critical patent/CN101084467B/en
Priority to JP2007539334A priority patent/JP4831777B2/en
Priority to EP05825085A priority patent/EP1820061B1/en
Priority to KR1020077010021A priority patent/KR101143748B1/en
Publication of WO2006057782A1 publication Critical patent/WO2006057782A1/en

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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/76Photosensitive materials characterised by the base or auxiliary layers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/091Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/075Silicon-containing compounds
    • G03F7/0752Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/0046Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20Exposure; Apparatus therefor
    • G03F7/2041Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means

Definitions

  • This invention relates to a top anti-reflective coating material (TARC) and barrier layer and the use thereof in lithography processes.
  • TARC top anti-reflective coating material
  • This TARC / barrier layer may be especially useful for immersion lithography in which a liquid such as water is used as the exposure medium between the lens fixture of an exposure tool and the photoresist-coated wafer.
  • top coat materials have been used in photolithography as anti-reflective films on the top of a photoresist.
  • Top anti-reflective coating (TARC) materials can prevent the multiple interference of light that takes place within the photoresist layer during exposure.
  • CD critical dimension
  • the refractive index of the top coat material (n t ) should be at about the square root of the multiplication of the refractive index of the exposure medium (n m ) and the refractive index of the underlying photoresist (n r ). If the exposure medium is air as in the case for "dry" lithography, the optimal refractive index of the top coat material (n t ) should be at about the square root of the refractive index of the underlying photoresist (n r ), because the refractive index of air is roughly 1.
  • the TARC also requires transparency to the exposure light to prevent intensity loss of the light to the photoresist.
  • TARC materials are designed to be soluble in both water and aqueous base developer so that they can be applied directly from water solution and subsequently removed by the aqueous base developer during the develop stage.
  • Numerous top coat materials have been developed to meet these two requirements of optimal refractive index and solubility.
  • U.S. Patent Nos. 5,744,537 and 6,057,080 disclose aqueous-soluble TARC materials comprising a polymeric binder and a fluorocarbon compound, and which have nearly ideal refractive indexes on the order of 1.3-1.4.
  • U.S. Patent No. 5,879,853 also discloses a TARC material that is removable by a wet process.
  • U.S. Patent No. 6,274,295 discloses a TARC material comprising a light absorbing compound having a wavelength of maximum absorption higher than an exposure wavelength used to expose the photoresist. This TARC can also be water-soluble.
  • U.S. Patent No. 5,240,812 discloses a protective material for use as an overcoat film for acid catalyzed resist composition to prevent contamination from vapors of organic and inorganic bases. While not specifically disclosed as being a TARC, the overcoat can also be water soluble.
  • Other TARC materials include those disclosed in U.S. Patent Nos. 5,744,537 and 6,057,080, U.S. Patent No. 6,503,689, U.S. Patent Application Pub. No. 2003/0211417, U.S. Patent Application Pub. No. 2004/0013971 , and U.S. Patent Application Pub. No. 2004/0033436.
  • Immersion lithography offers the potential to extend the use of optical lithography to print smaller features.
  • air is replaced by a liquid medium such as water between the lens and the wafer.
  • NA numerical aperture
  • Immersion lithography has presented some concerns that certain components in the photoresist may leach out to the immersion medium and change the performance of the photoresist, or that the immersion medium may diffuse into the photoresist and affect the acid generation and may then interfere with the chemical amplification mechanism.
  • Much effort has been devoted to modifying photoresist formulations to insure that the above-mentioned problems will not occur during the immersion exposure process, but no photoresist has been developed which is both compatible with water as the proposed immersion medium and has acceptable performance characteristics.
  • a top coat material can be used between the immersion medium and the resist-coated wafer.
  • Such top coat material can prevent photoresist components from leaching into the immersion medium, and can also prevent permeation of the immersion medium into the photoresist film.
  • One of the requirements for the top coat material is its insolubility in the immersion medium.
  • the top coat material can also act as a TARC layer.
  • top coat material that is insoluble in water but soluble in aqueous base developer, and also has desired optical properties so that it can also be used as a TARC.
  • a top antireflective coating and barrier layer material comprising a polymer.
  • the polymer comprises at least one silicon-containing moiety and at least one aqueous base soluble moiety.
  • the polymer may illustratively comprise at least one monomer having the structure:
  • a method of forming a patterned material layer on a substrate comprises: providing a substrate having a material layer on a surface thereof; depositing a photoresist composition on the substrate to form a photoresist layer on the material layer; applying a top antireflective coating and barrier layer material on the photoresist layer, thereby forming a coated substrate, the top antireflective coating and barrier layer material comprising at least one silicon- containing moiety and at least one aqueous base soluble moiety; patternwise exposing the coated substrate to imaging radiation; removing simultaneously the top antireflective coating and barrier layer material and portions of the photoresist layer from the coated substrate, thereby forming a patterned photoresist layer on the material layer; and transferring the photoresist layer pattern to the material layer.
  • This invention is directed to a TARC / barrier layer which is easy to apply, transparent to 193nm light, with proper n and k values to reduce reflectivity.
  • the TARC / barrier layer of this invention is preferably insoluble in water but soluble in developer, and therefore can be used as TARC / barrier layer in immersion lithography and removed in the develop stage.
  • the invention encompasses a top coat material comprising a polymer which comprises at least one silicon-containing moiety and at least one aqueous base soluble moiety.
  • the top coat is preferably insoluble in water but soluble in aqueous base developer so that it can be used for immersion lithography, especially 193nm immersion lithography.
  • the top coat material of the present invention can be adjusted to act as a TARC so that better process control of image formation can be achieved.
  • the optimal refractive index for a TARC material is about 1.5 to 1.7.
  • the Si moieties in the polymer of this invention may be, for example, Si-Si, Si-C, Si-N or Si-O moieties.
  • Preferred Si moieties are the SiO moieties.
  • the polymer containing SiO moieties may be a polymer containing SiO moieties in the polymer backbone and/or in pendant groups.
  • the polymer contains SiO moieties in its backbone.
  • the polymer is preferably an organosiloxane, more preferably an organosilsesquioxane.
  • the polymer should have solution and film-forming characteristics conducive to forming a layer by conventional spin-coating.
  • the polymer also preferably contains a plurality of aqueous base soluble sites distributed along the polymer for base soluble characteristics.
  • Base soluble moieties may include hydroxyl, carboxylic acid, sulfonamide, dicarboxyimide, N-hydroxy dicarboxyimide, any other amino group or any imino group.
  • the base soluble moiety is a hydroxyl group, and more preferably a fluoroalcohol moiety.
  • TARC / barrier layer polymers examples include polymers having a silsesquioxane (ladder or network) structure. Such polymers preferably contain monomers having the following structure:
  • Ri comprises an aqueous base soluble moiety, and x is from about 1 to about 1.95, more preferably from about 1 to about 1.75.
  • the aqueous base soluble moiety in Ri is preferably a hydroxyl or carboxylic acid moiety, more preferably a hydroxyl moiety, most preferably a fluoroalcohol.
  • Other acceptable aqueous base soluble moieties in Ri include sulfonamides, dicarboxyimides, N-hydroxy dicarboxyimides, any other amino groups or any imino groups. Ri may also include fluorinated versions of such solubility promoting moieties.
  • the polymers described above most preferably contain monomers having the following structure:
  • each R 2 is independently selected from any of a fluorine, a fluorinated linear or branched alkyl, a fluorocycloalkyl, a fluoroaryl, and any combination thereof, and R 2 may optionally further include any of oxygen, sulfur or nitrogen; each A is independently selected from any one of an oxygen atom, a sulfur atom, NR 3 , a linear or branched alkyl, a linear or a branched fluoroalkyl, a cycloalkyl or fluorocycloalkyl, and a fluoroaryl; p is an integer having the value 0 or 1 (i.e., including a single bond between a silicon atom of the silsesquioxane group and a carbon atom of a side group); each R 3 is independently selected from any of hydrogen, halogen, linear or branched alkyl, linear or branched fluoroalkyl
  • R 2 and R 3 may optionally further include any of oxygen, sulfur or nitrogen, or any combination thereof.
  • monomers having structure (II) may include, but are not limited to:
  • the present invention may further comprise a monomer unit with the following structure:
  • monomers having structure (Xl) may include, but are not limited to:
  • the polymer of the present invention may further comprise a monomer unit with the following structure:
  • R 6 represents a tertiary alkyl group such as t-butyl group, 1-methylcyclopentyl, 1 -ethylcyclopentyl, 1 -methylcyclohexyl, and t-amyl group, 1 -alkoxyethyl group such as isobomyl group, 1 -ethoxyethyl group, 1 -butoxyethyl group, 1 -isobutoxyethyl group and 1 -cylohexyloxyethyl group, alkoxymethyl group such as 1-methoxymethyl group, 1 -methoxypropyl, 1 - methoxycyclohexyl and 1 -ethoxymethyl group, 3-oxoalkyl group, tetrahydropyranyl group, tetrahydrofuranyl group, trialkylsilylester group, 3-oxocyclohexylester group, 2-methyl
  • the monomer having structure (XVI) may include, but is not limited to:
  • the TARC / barrier layer may further comprise at least one solvent which is preferably immiscible with the underlying photoresist material.
  • suitable solvents include, but are not limited to: 1 -butanol, methanol, ethanol, 1 -propanol, ethylene glycol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,2-propanediol, 1 -methyl-2-butanol, 1 -pentanol, 2-pentanol, 3-pentanol, 1- hexanol, 2-hexanol, 3-hexanol,1 -heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-methyl-1 -pentanol, 2-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl- 1 -pentanol, 3-
  • the TARC / barrier layer of the invention is preferably insoluble in water but is soluble in aqueous base developer.
  • the top coat material is preferably substantially optically transparent to the exposure radiation for the underlying photoresist material, to allow patterning of the photoresist material.
  • the TARC / barrier layer have a refractive index in the range of about 1.2 to 1.8.
  • the refractive index of the top coat material is most preferably in the range of about 1.5 to 1.7.
  • the TARC / barrier layer may be used in a method of forming a patterned material layer on a substrate.
  • the material layer may be, for example, a ceramic, dielectric, metal or semiconductor layer, such as those used in the manufacture of high performance integrated circuit devices and associated chip carrier packages.
  • a photoresist composition is first deposited on the substrate by known means, to form a photoresist layer on the material.
  • the substrate with the resist layer then may be baked, in a pre-exposure bake step, to remove any solvent from the photoresist composition and improve the coherence of the resist layer.
  • Typical pre-exposure baking temperature is about 80 to about 150 0 C.
  • Typical resist thickness is about 100 to about 500 nm.
  • the TARC / barrier layer of the invention is applied on the photoresist layer, thereby forming a coated substrate.
  • the coated substrate is then exposed to an appropriate irradiation source, through a patterned mask.
  • the imaging radiation is 193 nm radiation.
  • the imaging radiation is 157 nm radiation.
  • the imaging radiation is 248 nm radiation.
  • the coated substrate also may be exposed to such imaging radiation using immersion lithography, wherein an imaging medium is applied to the coated substrate prior to exposure.
  • the imaging medium is water.
  • the coated substrate is then contacted with an aqueous base developer, such as 0.263 N tetramethyl ammonium hydroxide (TMAH), thereby removing the top coat material and a portion of the photoresist layer simultaneously from the coated substrate.
  • aqueous base developer such as 0.263 N tetramethyl ammonium hydroxide (TMAH)
  • TMAH 0.263 N tetramethyl ammonium hydroxide
  • the pattern in the photoresist layer then may be transferred to the material layer on the underlying substrate. Typically, the transfer is achieved by reactive ion etching or some other etching technique.
  • the method of the invention may be used to create patterned material layer structures such as metal wiring lines, holes for contacts or vias, insulation sections (e.g., damascene trenches or shallow trench isolation), and trenches for capacitor structures, as might be used in the design of integrated circuit devices.
  • the processes for making these (ceramic, dielectric, metal or semiconductor) features generally involve providing a material layer or section of the substrate to be patterned, applying a layer of resist over the material layer or section, applying a top coat layer on the layer of resist, patternwise exposing the top coat and resist layers to radiation, developing the pattern by contacting the exposed top coat and resist with a developer, etching the layer(s) underlying the resist layer at spaces in the pattern whereby a patterned material layer or substrate is formed, and removing any remaining resist from the substrate.
  • a hard mask may be used below the resist layer to facilitate transfer of the pattern to a further underlying material layer or section. It should be understood that the invention is not limited to any specific lithography technique or device structure.
  • the typical thickness of the TARC / barrier layer is about 30-80 nm.
  • the TARC / barrier layer is applied to a thickness of about 1 -4 ⁇ m to act as in an situ pellicle to prevent particles or microbubbles from creating defects on resist.
  • the thick top coat will also improve process window of photoresists.
  • Poly(2-hydroxy-3,3,3-trifluoropropylsilsesquioxane) (structure illustrated below) was dissolved in 1-butanol to produce two solutions: 1.5 wt% solution and 5 wt% solution. These two solutions were then spin-coated on HMDS primed Si wafers, and the films were baked at 110 0 C for 60 seconds.
  • TARC / barrier layer compositions prepared in Examples 1 and 2 were spin-coated on silicon wafers, baked on hot plate at 110 0 C for 60 sec, then n and k values were measured with VB-250 VASE Ellipsometer manufactured by J. A. Woollam Co. Inc.
  • the optical properties of the film for 193 nm radiation are as shown in Table 2 below. Table 2. Optical properties evaluation
  • Lithography exposures were performed on both wafers with a 193 nm 0.75 NA optical scanner, with conventional illumination and a partial coherence of 0.6.
  • An attenuated phase shift test reticle was used with isolated line features of nominally 65 nm width.
  • a post exposure bake was performed, and the resists were developed in 0.26 N TMAH developer.
  • the TARC is also soluble in this developer, and was easily removed. Exposure dose was varied to find the proper anchor dose for these features and cross section SEMs were obtained.
  • the SEM for the control wafer showed 193 nm lithography patterning of an isolated line without application of the TARC.
  • the SEM for the second wafer showed an identical 193 nm lithography process with the TARC discussed above, and demonstrates that application of the topcoat does not affect the linewidth or lithography profile to any significant degree.
  • This example demonstrates successful 193 nm lithography with the TARC formulation discussed above. Note that this case is merely an example, and many other photoresists (including bilayer 193 nm resists) and processing conditions and equipment can be used with equal success.

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  • Engineering & Computer Science (AREA)
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  • Materials Engineering (AREA)
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Abstract

A top anti-reflective coating material (TARC) and barrier layer, and the use thereof in lithography processes, is disclosed. The TARC / barrier layer may be especially useful for immersion lithography using water as the imaging medium. The TARC / barrier layer comprises a polymer which comprises at least one silicon-containing moiety and at least one aqueous base soluble moiety. Suitable polymers include polymers having a silsesquioxane (ladder or network) structure, such as polymers containing monomers having the structure (I): where R1 comprises an aqueous base soluble moiety, and x is from about 1 to about 1.95, more preferably from about 1 to about 1.75.

Description

SILICON CONTAINING TARC / BARRIER LAYER
BACKGROUND OF THE INVENTION
Field of the Invention
This invention relates to a top anti-reflective coating material (TARC) and barrier layer and the use thereof in lithography processes. This TARC / barrier layer may be especially useful for immersion lithography in which a liquid such as water is used as the exposure medium between the lens fixture of an exposure tool and the photoresist-coated wafer.
Description of the Related Art
Traditionally, top coat materials have been used in photolithography as anti-reflective films on the top of a photoresist. Top anti-reflective coating (TARC) materials can prevent the multiple interference of light that takes place within the photoresist layer during exposure. As a result, the critical dimension (CD) variation of the geometrical features of a photoresist pattern that is caused by the variation in the thickness of the photoresist film can be minimized.
To fully take advantage of the anti-reflective effect of the top coat, the refractive index of the top coat material (nt) should be at about the square root of the multiplication of the refractive index of the exposure medium (nm) and the refractive index of the underlying photoresist (nr). If the exposure medium is air as in the case for "dry" lithography, the optimal refractive index of the top coat material (nt) should be at about the square root of the refractive index of the underlying photoresist (nr), because the refractive index of air is roughly 1. The TARC also requires transparency to the exposure light to prevent intensity loss of the light to the photoresist.
For ease of processing, classic TARC materials are designed to be soluble in both water and aqueous base developer so that they can be applied directly from water solution and subsequently removed by the aqueous base developer during the develop stage. Numerous top coat materials have been developed to meet these two requirements of optimal refractive index and solubility. For example, U.S. Patent Nos. 5,744,537 and 6,057,080 disclose aqueous-soluble TARC materials comprising a polymeric binder and a fluorocarbon compound, and which have nearly ideal refractive indexes on the order of 1.3-1.4. U.S. Patent No. 5,879,853 also discloses a TARC material that is removable by a wet process. U.S. Patent No. 5,595,861 similarly discloses a TARC comprising partially fluorinated compounds, which can also be water soluble. U.S. Patent No. 6,274,295 discloses a TARC material comprising a light absorbing compound having a wavelength of maximum absorption higher than an exposure wavelength used to expose the photoresist. This TARC can also be water-soluble. U.S. Patent No. 5,240,812 discloses a protective material for use as an overcoat film for acid catalyzed resist composition to prevent contamination from vapors of organic and inorganic bases. While not specifically disclosed as being a TARC, the overcoat can also be water soluble. Other TARC materials include those disclosed in U.S. Patent Nos. 5,744,537 and 6,057,080, U.S. Patent No. 6,503,689, U.S. Patent Application Pub. No. 2003/0211417, U.S. Patent Application Pub. No. 2004/0013971 , and U.S. Patent Application Pub. No. 2004/0033436.
Immersion lithography offers the potential to extend the use of optical lithography to print smaller features. In immersion lithography, air is replaced by a liquid medium such as water between the lens and the wafer. Use of a medium with an index of refraction higher than air results in a greater numerical aperture (NA) provided that the projection angle is kept the same in the medium, and therefore allows printing of smaller features.
Immersion lithography, however, has presented some concerns that certain components in the photoresist may leach out to the immersion medium and change the performance of the photoresist, or that the immersion medium may diffuse into the photoresist and affect the acid generation and may then interfere with the chemical amplification mechanism. Much effort has been devoted to modifying photoresist formulations to insure that the above-mentioned problems will not occur during the immersion exposure process, but no photoresist has been developed which is both compatible with water as the proposed immersion medium and has acceptable performance characteristics.
To alleviate these photoresist leaching and solubility problems in immersion lithography, a top coat material can be used between the immersion medium and the resist-coated wafer. Such top coat material can prevent photoresist components from leaching into the immersion medium, and can also prevent permeation of the immersion medium into the photoresist film. One of the requirements for the top coat material, of course, is its insolubility in the immersion medium. Preferably, the top coat material can also act as a TARC layer.
Water has been proposed as the immersion medium for 193nm immersion lithography. Therefore, classic water-soluble TARC materials such as those described above can not be used as top coats for 193nm immersion lithography. Moreover, since water has higher refractive index (1.437 at 193nm) than air (~1 at 193nm), the optimal refractive index for TARC materials used for 193nm immersion lithography is also higher than that of classic TARCs.
Thus, there remains a need for a top coat material that is insoluble in water but soluble in aqueous base developer, and also has desired optical properties so that it can also be used as a TARC.
SUMMARY OF THE INVENTION
In a first aspect of the invention, a top antireflective coating and barrier layer material comprising a polymer is provided. The polymer comprises at least one silicon-containing moiety and at least one aqueous base soluble moiety. The polymer may illustratively comprise at least one monomer having the structure:
-SiOx- ( O wherein R1 comprises an aqueous base soluble moiety, and x is about 1 to about 1.95.
In a second aspect of the invention, a method of forming a patterned material layer on a substrate is provided. The method comprises: providing a substrate having a material layer on a surface thereof; depositing a photoresist composition on the substrate to form a photoresist layer on the material layer; applying a top antireflective coating and barrier layer material on the photoresist layer, thereby forming a coated substrate, the top antireflective coating and barrier layer material comprising at least one silicon- containing moiety and at least one aqueous base soluble moiety; patternwise exposing the coated substrate to imaging radiation; removing simultaneously the top antireflective coating and barrier layer material and portions of the photoresist layer from the coated substrate, thereby forming a patterned photoresist layer on the material layer; and transferring the photoresist layer pattern to the material layer.
DETAILED DESCRIPTION OF THE INVENTION
This invention is directed to a TARC / barrier layer which is easy to apply, transparent to 193nm light, with proper n and k values to reduce reflectivity. Moreover, the TARC / barrier layer of this invention is preferably insoluble in water but soluble in developer, and therefore can be used as TARC / barrier layer in immersion lithography and removed in the develop stage.
The invention encompasses a top coat material comprising a polymer which comprises at least one silicon-containing moiety and at least one aqueous base soluble moiety. The top coat is preferably insoluble in water but soluble in aqueous base developer so that it can be used for immersion lithography, especially 193nm immersion lithography. Additionally, the top coat material of the present invention can be adjusted to act as a TARC so that better process control of image formation can be achieved. For 193nm immersion lithography using water as the exposure medium, the optimal refractive index for a TARC material is about 1.5 to 1.7.
The Si moieties in the polymer of this invention may be, for example, Si-Si, Si-C, Si-N or Si-O moieties. Preferred Si moieties are the SiO moieties. The polymer containing SiO moieties may be a polymer containing SiO moieties in the polymer backbone and/or in pendant groups. Preferably, the polymer contains SiO moieties in its backbone. The polymer is preferably an organosiloxane, more preferably an organosilsesquioxane. The polymer should have solution and film-forming characteristics conducive to forming a layer by conventional spin-coating.
In addition to the SiO moieties, the polymer also preferably contains a plurality of aqueous base soluble sites distributed along the polymer for base soluble characteristics. Base soluble moieties may include hydroxyl, carboxylic acid, sulfonamide, dicarboxyimide, N-hydroxy dicarboxyimide, any other amino group or any imino group. Preferably, the base soluble moiety is a hydroxyl group, and more preferably a fluoroalcohol moiety.
Examples of suitable TARC / barrier layer polymers include polymers having a silsesquioxane (ladder or network) structure. Such polymers preferably contain monomers having the following structure:
- ΨSiOx- ( D where Ri comprises an aqueous base soluble moiety, and x is from about 1 to about 1.95, more preferably from about 1 to about 1.75. The aqueous base soluble moiety in Ri is preferably a hydroxyl or carboxylic acid moiety, more preferably a hydroxyl moiety, most preferably a fluoroalcohol. Other acceptable aqueous base soluble moieties in Ri include sulfonamides, dicarboxyimides, N-hydroxy dicarboxyimides, any other amino groups or any imino groups. Ri may also include fluorinated versions of such solubility promoting moieties.
The polymers described above most preferably contain monomers having the following structure:
OH R2-C-R3
(A )p -SiOx- ( I D where: each R2 is independently selected from any of a fluorine, a fluorinated linear or branched alkyl, a fluorocycloalkyl, a fluoroaryl, and any combination thereof, and R2 may optionally further include any of oxygen, sulfur or nitrogen; each A is independently selected from any one of an oxygen atom, a sulfur atom, NR3, a linear or branched alkyl, a linear or a branched fluoroalkyl, a cycloalkyl or fluorocycloalkyl, and a fluoroaryl; p is an integer having the value 0 or 1 (i.e., including a single bond between a silicon atom of the silsesquioxane group and a carbon atom of a side group); each R3 is independently selected from any of hydrogen, halogen, linear or branched alkyl, linear or branched fluoroalkyl, cycloalkyl, fluorocycloalkyl, fluoroaryl, and any combination thereof; and
R2 and R3 may optionally further include any of oxygen, sulfur or nitrogen, or any combination thereof.
In exemplary embodiments of the present invention, monomers having structure (II) may include, but are not limited to:
Figure imgf000008_0001
To tune the dissolution rates and n and k values of the TARC / barrier layer, the present invention may further comprise a monomer unit with the following structure:
R4 -SiOx- (XI ) where R4 comprises a polar organic moiety which may be selected from the group consisting of lactones, anhydrides, esters, ethers and alcohols, and fluorinated versions of such polar organic moieties; and x is from about 1 to about 1.95, more preferably from about 1 to about 1.75.
In exemplary embodiments of the present invention, monomers having structure (Xl) may include, but are not limited to:
Figure imgf000009_0001
To enhance the dissolution contrast of the resist under the TARC / barrier layer, the polymer of the present invention may further comprise a monomer unit with the following structure:
R5 -SiOx- (XVI ) where R5 comprises an acid labile moiety which may be selected from the group consisting of t-butyl ester, anhydrides, esters, ethers and alcohols, and fluorinated versions of such acid labile moieties; and x is from about 1 to about 1.95, more preferably from about 1 to about 1.75.
The structure of the acid-decomposable group in R5 is represented by
0 Il — C-X-R6 (XVI I ) or
-X-R6 (XVI I I ) where R6 represents a tertiary alkyl group such as t-butyl group, 1-methylcyclopentyl, 1 -ethylcyclopentyl, 1 -methylcyclohexyl, and t-amyl group, 1 -alkoxyethyl group such as isobomyl group, 1 -ethoxyethyl group, 1 -butoxyethyl group, 1 -isobutoxyethyl group and 1 -cylohexyloxyethyl group, alkoxymethyl group such as 1-methoxymethyl group, 1 -methoxypropyl, 1 - methoxycyclohexyl and 1 -ethoxymethyl group, 3-oxoalkyl group, tetrahydropyranyl group, tetrahydrofuranyl group, trialkylsilylester group, 3-oxocyclohexylester group, 2-methyl-2-adamantyl group, 2-methyl-2- isobornyl, 2-ethyl-2-tetracyclododecenyl, mevalonic lactone residue or 2-{γ- butyrolactonyl-oxycarbonyl)-2-propyl group; and X represents an oxygen atom, sulfur atom, -NH-, -NHSO2- or -NHSO2NH-.
In exemplary embodiments of the present invention, the monomer having structure (XVI) may include, but is not limited to:
Figure imgf000010_0001
The TARC / barrier layer may further comprise at least one solvent which is preferably immiscible with the underlying photoresist material. Suitable solvents include, but are not limited to: 1 -butanol, methanol, ethanol, 1 -propanol, ethylene glycol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,2-propanediol, 1 -methyl-2-butanol, 1 -pentanol, 2-pentanol, 3-pentanol, 1- hexanol, 2-hexanol, 3-hexanol,1 -heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-methyl-1 -pentanol, 2-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl- 1 -pentanol, 3-methyl-2-pentanol, 3-methyl-3-pentanol, 4-methyl-1-pentanol, 4- methyl-2-pentanol, 2,4-dimethyl-3-pentanol, 3-ethyl-2-pentanol, 1 - methylcyclopentanol, 2-methyl-1-hexanol, 2-methyl-2-hexanol, 2-methyl-3- hexanol, 3-methyl-3-hexanol, 4-methyl-3-hexanol, 5-methyl-1 -hexanol, 5- methyl-2-hexanol, 5-methyl-3-hexanol, 4-methylcyclohexanol, and 1 ,3-propanediol. The TARC / barrier layer of the invention is preferably insoluble in water but is soluble in aqueous base developer. Moreover, the top coat material is preferably substantially optically transparent to the exposure radiation for the underlying photoresist material, to allow patterning of the photoresist material.
It is also preferable that the TARC / barrier layer have a refractive index in the range of about 1.2 to 1.8. For 193nm immersion lithography using water as the exposure medium, the refractive index of the top coat material is most preferably in the range of about 1.5 to 1.7.
In another aspect of the invention, the TARC / barrier layer may be used in a method of forming a patterned material layer on a substrate. The material layer may be, for example, a ceramic, dielectric, metal or semiconductor layer, such as those used in the manufacture of high performance integrated circuit devices and associated chip carrier packages. In the method, a photoresist composition is first deposited on the substrate by known means, to form a photoresist layer on the material. The substrate with the resist layer then may be baked, in a pre-exposure bake step, to remove any solvent from the photoresist composition and improve the coherence of the resist layer. Typical pre-exposure baking temperature is about 80 to about 150 0C. Typical resist thickness is about 100 to about 500 nm.
Next, the TARC / barrier layer of the invention is applied on the photoresist layer, thereby forming a coated substrate. The coated substrate is then exposed to an appropriate irradiation source, through a patterned mask. In one exemplary embodiment, the imaging radiation is 193 nm radiation. In another embodiment, the imaging radiation is 157 nm radiation. In another embodiment, the imaging radiation is 248 nm radiation. The coated substrate also may be exposed to such imaging radiation using immersion lithography, wherein an imaging medium is applied to the coated substrate prior to exposure. In a preferred embodiment, the imaging medium is water. The coated substrate is then contacted with an aqueous base developer, such as 0.263 N tetramethyl ammonium hydroxide (TMAH), thereby removing the top coat material and a portion of the photoresist layer simultaneously from the coated substrate. Contact with developer forms a patterned photoresist layer on the material layer.
The pattern in the photoresist layer then may be transferred to the material layer on the underlying substrate. Typically, the transfer is achieved by reactive ion etching or some other etching technique. The method of the invention may be used to create patterned material layer structures such as metal wiring lines, holes for contacts or vias, insulation sections (e.g., damascene trenches or shallow trench isolation), and trenches for capacitor structures, as might be used in the design of integrated circuit devices.
The processes for making these (ceramic, dielectric, metal or semiconductor) features generally involve providing a material layer or section of the substrate to be patterned, applying a layer of resist over the material layer or section, applying a top coat layer on the layer of resist, patternwise exposing the top coat and resist layers to radiation, developing the pattern by contacting the exposed top coat and resist with a developer, etching the layer(s) underlying the resist layer at spaces in the pattern whereby a patterned material layer or substrate is formed, and removing any remaining resist from the substrate. In some instances, a hard mask may be used below the resist layer to facilitate transfer of the pattern to a further underlying material layer or section. It should be understood that the invention is not limited to any specific lithography technique or device structure.
The typical thickness of the TARC / barrier layer is about 30-80 nm. In another embodiment of this invention, the TARC / barrier layer is applied to a thickness of about 1 -4 μm to act as in an situ pellicle to prevent particles or microbubbles from creating defects on resist. The thick top coat will also improve process window of photoresists. The following non-limiting examples are provided to further illustrate the present invention. Because these examples are provided for illustrative purposes only, the invention embodied therein should be limited thereto.
Example 1. Water treatment evaluation
Poly(2-hydroxy-3,3,3-trifluoropropylsilsesquioxane) (structure illustrated below) was dissolved in 1-butanol to produce two solutions: 1.5 wt% solution and 5 wt% solution. These two solutions were then spin-coated on HMDS primed Si wafers, and the films were baked at 110 0C for 60 seconds.
Figure imgf000013_0001
The following water solubility test was then conducted. The coated substrate was immersed in water for 3 minutes. Results are shown in Table 1. Thickness measured before and after immersion confirmed that there was no thickness loss of the TARC / barrier layer material in water. The slight variation is within the measurement error.
Table 1. Water treatment evaluation
Figure imgf000013_0002
Example 2. Active TARC / barrier layer evaluation
Poly[2-hydroxy-3,3,3-trifluoropropylsilsesquioxane-co-5-(2-t-butoxy- carbonyl)norbomylsilsesquioxane] (structure illustrated below) was dissolved in 1 -butanol to provide a solution having 1.5 wt% solid. This active ARC / barrier layer was applied over photoresist (AMX2073, from JSR) coated quartz disks. Photoresist thickness was around 280 nm. The films were baked at 110 0C for 60 seconds, and then flood exposed for 0.1 second with broadband DUV light using a flood exposure tool manufactured by Fusion System Corporation, Rockville, Maryland. After exposure, the quartz disks containing photoresist and active ARC / barrier layer were baked then developed in 0.263N TMAH and monitored with Research Quartz Crystal Microbalance (RQCM, RS-232) tool manufactured by Maxtek, Inc.
Figure imgf000014_0001
This experiment indicates when the whole assembly was baked at 110 0C for 60 seconds after exposure, the whole stack dissolved in less than one second. When the whole assembly was baked at 110 0C for 20 seconds after exposure, there was no dissolution for the first 1.5 seconds, and then the whole stack took 4.75 seconds to dissolve. The regular baking process after exposure for the resist alone is 110 0C for 60 seconds.
Example 3. Optical properties evaluation
The TARC / barrier layer compositions prepared in Examples 1 and 2 were spin-coated on silicon wafers, baked on hot plate at 110 0C for 60 sec, then n and k values were measured with VB-250 VASE Ellipsometer manufactured by J. A. Woollam Co. Inc. The optical properties of the film for 193 nm radiation are as shown in Table 2 below. Table 2. Optical properties evaluation
Figure imgf000015_0001
Example 4. Lithographic evaluation of TARC / barrier layer
Commercial 193 nm resist films and corresponding ARCs were spin cast on two 200 mm silicon wafers on a TEL ACT8 lithography processing track. The initial films were about 250 nm in thickness. The resist films were baked at 1300C for 60 sec. On one of these wafers, the TARC material described in Example 1 (1.5 wt% solution of Poly(2-hydroxy-3,3,3- trifluoropropylsilsesquioxane)) above was spun onto the resist film at a thickness of 40 nm. The wafer was then baked at 1100C for 60 sec.
Lithography exposures were performed on both wafers with a 193 nm 0.75 NA optical scanner, with conventional illumination and a partial coherence of 0.6. An attenuated phase shift test reticle was used with isolated line features of nominally 65 nm width. A post exposure bake was performed, and the resists were developed in 0.26 N TMAH developer. The TARC is also soluble in this developer, and was easily removed. Exposure dose was varied to find the proper anchor dose for these features and cross section SEMs were obtained. The SEM for the control wafer showed 193 nm lithography patterning of an isolated line without application of the TARC. The SEM for the second wafer showed an identical 193 nm lithography process with the TARC discussed above, and demonstrates that application of the topcoat does not affect the linewidth or lithography profile to any significant degree. This example demonstrates successful 193 nm lithography with the TARC formulation discussed above. Note that this case is merely an example, and many other photoresists (including bilayer 193 nm resists) and processing conditions and equipment can be used with equal success.
While the present invention has been particularly described in conjunction with a specific preferred embodiment and other alternative embodiments, it is evident that numerous alternatives, modifications and variations will be apparent to those skilled in the art in light of the foregoing description. It is therefore intended that the appended claims embrace all such alternatives, modifications and variations as falling within the true scope and spirit of the present invention.

Claims

We claim:
1. A top anti reflective coating and barrier layer material comprising: a polymer comprising at least one silicon-containing moiety and at least one aqueous base soluble moiety.
2. The top antireflective coating and barrier layer material of Claim 1 , wherein the antireflective coating and barrier layer material has a refractive index of about 1.5 to 1.7.
3. The top antireflective coating and barrier layer material of Claim 1 , wherein said polymer further comprises at least one fluorine-containing moiety.
4. The top antireflective coating and barrier layer material of Claim 1 , wherein said silicon-containing moiety comprises Si-Si, Si-C, Si-N or Si-O.
5. The top antireflective coating and barrier layer material of Claim 1 , wherein said silicon-containing moiety comprises SiO.
6. The top antireflective coating and barrier layer material of Claim 5, wherein said polymer is a organosiloxane.
7. The top antireflective coating and barrier layer material of Claim 6, wherein said polymer is an organosilsesquioxane.
8. The top antireflective coating and barrier layer material of Claim 1 , wherein said at least one aqueous base soluble moiety is selected from the group consisting of hydroxyl, carboxylic acid, sulfonamide, dicarboxyimide, N- hydroxy dicarboxyimide, an amino group, and an imino group.
9. The top antireflective coating and barrier layer material of Claim 8, wherein said at least one aqueous base soluble moiety is a fluoroalcohol.
10. The top antireflective coating and barrier layer material of Claim 9, wherein said fluoroalcohol is trifluorocarbinol or hexafluorocarbinol.
11. The top antireflective coating and barrier layer material of Claim 1 , wherein said polymer further comprises at least one acid labile moiety.
12. The top antireflective coating and barrier layer material of Claim 1 , further comprising at least one solvent selected from the group consisting of 1 -butanol, methanol, ethanol, 1-propanol, ethylene glycol, 1 ,2-butanediol, 1 ,3- butanediol, 1 ,4-butanediol, 1 ,2-propanediol, 1-methyl-2-butanol, 1 -pentanol, 2-pentanol, 3-pentanol, 1 -hexanol, 2-hexanol, 3-hexanol,1-heptanol, 2- heptanol, 3-heptanol, 4-heptanol, 2-methyl-1-pentanol, 2-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl-1-pentanol, 3-methyl-2-pentanol, 3-methyl- 3-pentanol, 4-methyl-1 -pentanol, 4-methyl-2-pentanol, 2,4-dimethyl-3- pentanol, 3-ethyl-2-pentanol, 1 -methylcyclopentanol, 2-methyl-1 -hexanol, 2- vmethyl-2-hexanol, 2-methyl-3-hexanol, 3-methyl-3-hexanol, 4-methyl-3- hexanol, 5-methyl-1 -hexanol, 5-methyl-2-hexanol, 5-methyl-3-hexanol, 4- methylcyclohexanol, and 1 ,3-propanediol.
13. The top antireflective coating and barrier layer material of Claim 7, wherein said polymer comprises at least one monomer having the structure:
— SiOx- ( D wherein Ri comprises an aqueous base soluble moiety, and x is about 1 to about 1.95.
14. The top antireflective coating and barrier layer material of Claim 13, wherein said an aqueous base soluble moiety is selected from the group consisting of hydroxyl, carboxylic acid, sulfonamide, dicarboxyimide, N- hydroxy dicarboxyimide, an amino group, and an imino group.
15. The top antireflective coating and barrier layer material of Claim 14, wherein said an aqueous base soluble moiety is a fluoroalcohol.
16. The top antireflective coating and barrier layer material of Claim 1 , wherein the polymer comprises at least one monomer having the structure:
OH R2-C-R3
(A )p — SiOx- ( I D wherein each R2 is independently selected from the group consisting of a fluorine, a fluorinated linear or branched alkyl, a fluorocycloalkyl, a fluoroaryl, and any combination thereof; each A is independently selected from the group consisting of an oxygen atom, a sulfur atom, NR3, a linear or branched alkyl, a linear or a branched fluoroalkyl, a cycloalkyl or fluorocycloalkyl, and a fluoroaryl; p is 0 or 1 ; and each R3 is independently selected from the group consisting of hydrogen, halogen, linear or branched alkyl, linear or branched fluoroalkyl, cycloalkyl, fluorocycloalkyl, fluoroaryl, and any combination thereof.
17. The top antireflective coating and barrier layer material of Claim 16, wherein R2 and R3 further comprises at least one of oxygen, sulfur and nitrogen.
18. The top antireflective coating and barrier layer material of Claim 16, wherein the at least one monomer is selected from the group consisting of:
Figure imgf000020_0001
19. The top antireflective coating and barrier layer material of Claim 13, wherein the polymer further comprises at least one co-monomer having the structure:
-SiOx- (XI ) wherein R4 comprises a polar organic moiety selected from the group consisting of lactones, anhydrides, esters, ethers and alcohols; and x is from about 1 to about 1.95.
20. The top antireflective coating and barrier layer material of Claim 19, wherein said co-monomer is selected from the group consisting of:
Figure imgf000021_0001
21. The top antireflective coating and barrier layer material of Claim 13, wherein the polymer further comprises at least one co-monomer having the structure:
-SiOx- (XVI ) wherein R5 comprises an acid labile moiety selected from the group consisting of t-butyl ester, anhydride, ester, ether and alcohol; and x is from about 1 to about 1.95.
22. The top antireflective coating and barrier layer material of Claim 21 , wherein said acid labile moiety is selected from the group consisting of:
0
-C-X-R6 (XVI I ) and
_χ_R6 (XVI I I ) wherein R6 is selected from the group consisting of a tertiary alkyl group, 1 -alkoxyethyl group, alkoxymethyl group, 3-oxoalkyl group, tetrahydropyranyl group, tetrahydrofuranyl group, trialkylsilyl ester group, 3-oxocyclohexylester group, 2-methyl-2-adamantyl group, 2-methyl-2-isobornyl, 2-ethyl-2- tetracyclododecenyl, mevalonic lactone residue and 2-(y-butyrolactonyl oxycarbonyl)-2-propyl group; and X is selected from the group consisting of oxygen, sulfur, -NH-, -NHSO2- and -NHSO2NH-.
23. The top antireflective coating and barrier layer material of Claim 22, wherein the at least one co-monomer is selected from the group consisting of:
Figure imgf000022_0001
24. A method of forming a patterned material layer on a substrate, the method comprising: providing a substrate having a material layer on a surface thereof; depositing a photoresist composition on the substrate to form a photoresist layer on the material layer; applying a top antireflective coating and barrier layer material on the photoresist layer, thereby forming a coated substrate, the top antireflective coating and barrier layer material comprising at least one silicon-containing moiety and at least one aqueous base soluble moiety; patternwise exposing the coated substrate to imaging radiation; removing simultaneously the top antireflective coating and barrier layer material and portions of the photoresist layer from the coated substrate, thereby forming a patterned photoresist layer on the material layer; and transferring the photoresist layer pattern to the material layer.
25. The method of Claim 24, wherein the top antireflective coating and barrier layer material and portions of the photoresist layer are removed by contacting the resist layer with an aqueous alkaline developer.
26. The method of Claim 25, wherein the aqueous alkaline developer is 0.263 N tetramethyl ammonium hydroxide.
27. The method of Claim 24, wherein the material layer is selected from the group consisting of ceramic, dielectric, metal and semiconductor layer.
28. The method of Claim 24, wherein the imaging radiation is 193 nm radiation.
29. The method of Claim 24, wherein the imaging radiation is 157 nm radiation.
30. The method of Claim 24, wherein the imaging radiation is 248 nm radiation.
31. The method of Claim 24, further comprising, prior to pattemwise exposing the coated substrate to imaging radiation, the step of applying an imaging medium to the coated substrate.
32. The method of Claim 31 , wherein the imaging medium is water.
33. The method of Claim 24, wherein the photoresist layer pattern is transferred to the material layer by removing portions of the material layer not covered by the patterned photoresist layer.
34. The method of Claim 33, wherein portions of the material layer are removed by etching the material layer in areas not covered by the patterned photoresist layer.
35. The method of Claim 34, wherein portions of the material layer are removed using reactive ion etching.
36. The method of Claim 24, wherein the top antireflective coating and barrier layer material has a thickness of about 1 to about 4 μm.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007226170A (en) * 2006-01-27 2007-09-06 Shin Etsu Chem Co Ltd Antireflection film material, substrate having antireflection film and pattern forming method
KR100893120B1 (en) * 2006-02-22 2009-04-14 에어 프로덕츠 앤드 케미칼스, 인코오포레이티드 Top coat for lithography processes
WO2014069329A1 (en) 2012-10-31 2014-05-08 日産化学工業株式会社 Ester-group-containing composition for forming silicon-containing resist underlayer film
KR20150097550A (en) 2012-12-19 2015-08-26 닛산 가가쿠 고교 가부시키 가이샤 Composition for forming silicon-containing resist underlayer film having cyclic diester group
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Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7781141B2 (en) * 2004-07-02 2010-08-24 Rohm And Haas Electronic Materials Llc Compositions and processes for immersion lithography
JP4551704B2 (en) * 2004-07-08 2010-09-29 富士フイルム株式会社 Protective film forming composition for immersion exposure and pattern forming method using the same
US7399581B2 (en) * 2005-02-24 2008-07-15 International Business Machines Corporation Photoresist topcoat for a photolithographic process
US7238624B2 (en) * 2005-03-01 2007-07-03 Taiwan Semiconductor Manufacturing Company, Ltd. System and method for manufacturing semiconductor devices using a vacuum chamber
JP5203575B2 (en) * 2005-05-04 2013-06-05 ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. Coating composition
US20060263724A1 (en) * 2005-05-17 2006-11-23 Joseph Chen Method for forming material layer between liquid and photoresist layer
US20070097347A1 (en) * 2005-10-28 2007-05-03 Toppan Chungwa Electronics Co., Ltd. Method for forming a circuit pattern by using two photo-masks
JP4739150B2 (en) * 2006-08-30 2011-08-03 富士通株式会社 Resist cover film forming material, resist pattern forming method, electronic device and manufacturing method thereof
KR101655251B1 (en) * 2008-02-18 2016-09-07 닛산 가가쿠 고교 가부시키 가이샤 Silicon-Containing Resist Underlayer Film-Forming Composition Containing Cyclic Amino Group
KR101445878B1 (en) * 2008-04-04 2014-09-29 삼성전자주식회사 Protecting film and encapsulation material comprising the same
KR20090107882A (en) * 2008-04-10 2009-10-14 삼성전자주식회사 Graded composition encapsulation thin film comprising anchoring layer and method of fabricating the same
US8084193B2 (en) * 2008-07-12 2011-12-27 International Business Machines Corporation Self-segregating multilayer imaging stack with built-in antireflective properties
KR101749604B1 (en) * 2008-08-18 2017-06-21 닛산 가가쿠 고교 가부시키 가이샤 Composition for Forming Silicon-Containing Resist Underlayer Film With Onium Group
KR20100071650A (en) * 2008-12-19 2010-06-29 삼성전자주식회사 Gas barrier thin film, electronic device comprising the same, and method for preparing the same
WO2010071155A1 (en) 2008-12-19 2010-06-24 日産化学工業株式会社 Silicon-containing resist underlayer film formation composition having anion group
JP5618095B2 (en) 2009-06-02 2014-11-05 日産化学工業株式会社 Silicon-containing resist underlayer film forming composition having sulfide bond
EP2479615B1 (en) * 2009-09-16 2014-04-23 Nissan Chemical Industries, Ltd. Silicon-containing composition having sulfonamide group for forming resist underlayer film
US9023588B2 (en) 2010-02-19 2015-05-05 Nissan Chemical Industries, Ltd. Resist underlayer film forming composition containing silicon having nitrogen-containing ring
US8323871B2 (en) * 2010-02-24 2012-12-04 International Business Machines Corporation Antireflective hardmask composition and a method of preparing a patterned material using same
JP5882776B2 (en) * 2012-02-14 2016-03-09 信越化学工業株式会社 Resist underlayer film forming composition and pattern forming method
US9017934B2 (en) 2013-03-08 2015-04-28 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist defect reduction system and method
US9175173B2 (en) 2013-03-12 2015-11-03 Taiwan Semiconductor Manufacturing Company, Ltd. Unlocking layer and method
US9543147B2 (en) 2013-03-12 2017-01-10 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist and method of manufacture
US9256128B2 (en) 2013-03-12 2016-02-09 Taiwan Semiconductor Manufacturing Company, Ltd. Method for manufacturing semiconductor device
US8932799B2 (en) 2013-03-12 2015-01-13 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist system and method
US9110376B2 (en) 2013-03-12 2015-08-18 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist system and method
US9354521B2 (en) 2013-03-12 2016-05-31 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist system and method
US9245751B2 (en) 2013-03-12 2016-01-26 Taiwan Semiconductor Manufacturing Company, Ltd. Anti-reflective layer and method
US9502231B2 (en) 2013-03-12 2016-11-22 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist layer and method
US9117881B2 (en) 2013-03-15 2015-08-25 Taiwan Semiconductor Manufacturing Company, Ltd. Conductive line system and process
US9341945B2 (en) 2013-08-22 2016-05-17 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist and method of formation and use
US10036953B2 (en) 2013-11-08 2018-07-31 Taiwan Semiconductor Manufacturing Company Photoresist system and method
US10095113B2 (en) 2013-12-06 2018-10-09 Taiwan Semiconductor Manufacturing Company Photoresist and method
US9761449B2 (en) 2013-12-30 2017-09-12 Taiwan Semiconductor Manufacturing Company, Ltd. Gap filling materials and methods
US9599896B2 (en) 2014-03-14 2017-03-21 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist system and method
US9581908B2 (en) 2014-05-16 2017-02-28 Taiwan Semiconductor Manufacturing Company, Ltd. Photoresist and method
TWI712860B (en) * 2015-02-26 2020-12-11 日商富士軟片股份有限公司 Pattern forming method, manufacturing method of electronic component, and sensitizing radiation-sensitive or radiation-sensitive resin composition for organic solvent development

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050079443A1 (en) * 2003-10-07 2005-04-14 Shin-Etsu Chemical Co., Ltd. Radiation-sensitive polymer composition and pattern forming method using the same

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2643056B2 (en) * 1991-06-28 1997-08-20 インターナショナル・ビジネス・マシーンズ・コーポレイション Surface anti-reflective coating forming composition and use thereof
JPH07253674A (en) * 1994-03-14 1995-10-03 Shin Etsu Chem Co Ltd Material for antireflection film
US6531260B2 (en) * 2000-04-07 2003-03-11 Jsr Corporation Polysiloxane, method of manufacturing same, silicon-containing alicyclic compound, and radiation-sensitive resin composition
US6951705B2 (en) * 2000-05-05 2005-10-04 E. I. Du Pont De Nemours And Company Polymers for photoresist compositions for microlithography
US6420088B1 (en) * 2000-06-23 2002-07-16 International Business Machines Corporation Antireflective silicon-containing compositions as hardmask layer
WO2002025374A2 (en) * 2000-09-19 2002-03-28 Shipley Company, L.L.C. Antireflective composition
US6974657B2 (en) * 2000-10-18 2005-12-13 E. I. Du Pont De Nemours And Company Compositions for microlithography
JP4088746B2 (en) * 2001-05-11 2008-05-21 信越化学工業株式会社 Polymer compound, chemically amplified resist material, and pattern forming method
US20040013971A1 (en) * 2001-11-21 2004-01-22 Berger Larry L Antireflective layer for use in microlithography
US6730454B2 (en) * 2002-04-16 2004-05-04 International Business Machines Corporation Antireflective SiO-containing compositions for hardmask layer
US6770419B2 (en) * 2002-09-11 2004-08-03 International Business Machines Corporation Low silicon-outgassing resist for bilayer lithography
JP4370898B2 (en) * 2002-12-17 2009-11-25 Jsr株式会社 Radiation sensitive resin composition
TWI310119B (en) * 2003-02-26 2009-05-21 Tokyo Ohka Kogyo Co Ltd Silsequioxane resin, positive photoresist composition, resist laminar body and resist pattern formation method
US7390609B2 (en) * 2003-03-03 2008-06-24 Rohm And Haas Electronic Materials Llc Polymers and photoresists comprising same
JP4262516B2 (en) * 2003-05-12 2009-05-13 富士フイルム株式会社 Positive resist composition
JP3993549B2 (en) * 2003-09-30 2007-10-17 株式会社東芝 Resist pattern forming method
US6939664B2 (en) * 2003-10-24 2005-09-06 International Business Machines Corporation Low-activation energy silicon-containing resist system
US20050106494A1 (en) * 2003-11-19 2005-05-19 International Business Machines Corporation Silicon-containing resist systems with cyclic ketal protecting groups
US7781141B2 (en) * 2004-07-02 2010-08-24 Rohm And Haas Electronic Materials Llc Compositions and processes for immersion lithography
JP2006113246A (en) * 2004-10-14 2006-04-27 Fuji Photo Film Co Ltd Protective film forming composition for liquid immersion exposure and pattern forming method using same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050079443A1 (en) * 2003-10-07 2005-04-14 Shin-Etsu Chemical Co., Ltd. Radiation-sensitive polymer composition and pattern forming method using the same

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007226170A (en) * 2006-01-27 2007-09-06 Shin Etsu Chem Co Ltd Antireflection film material, substrate having antireflection film and pattern forming method
KR100893120B1 (en) * 2006-02-22 2009-04-14 에어 프로덕츠 앤드 케미칼스, 인코오포레이티드 Top coat for lithography processes
WO2014069329A1 (en) 2012-10-31 2014-05-08 日産化学工業株式会社 Ester-group-containing composition for forming silicon-containing resist underlayer film
KR20150081269A (en) 2012-10-31 2015-07-13 닛산 가가쿠 고교 가부시키 가이샤 Ester-group-containing composition for forming silicon-containing resist underlayer film
US10372039B2 (en) 2012-10-31 2019-08-06 Nissan Chemical Industries, Ltd. Resist underlayer film forming composition containing silicon having ester group
KR20150097550A (en) 2012-12-19 2015-08-26 닛산 가가쿠 고교 가부시키 가이샤 Composition for forming silicon-containing resist underlayer film having cyclic diester group
US9290623B2 (en) 2012-12-19 2016-03-22 Nissan Chemical Industries, Ltd. Composition for forming silicon-containing resist underlayer film having cyclic diester group
KR20190135026A (en) 2017-03-31 2019-12-05 닛산 가가쿠 가부시키가이샤 Silicon-containing resist underlayer film forming composition having carbonyl structure

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TWI373484B (en) 2012-10-01
CN101084467A (en) 2007-12-05
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US7320855B2 (en) 2008-01-22
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TW200615306A (en) 2006-05-16
EP1820061A1 (en) 2007-08-22

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