WO2006057782A1 - Silicon containing tarc/barrier layer - Google Patents
Silicon containing tarc/barrier layer Download PDFInfo
- 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
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- barrier layer
- group
- antireflective coating
- methyl
- layer material
- Prior art date
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; 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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- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Silicon Polymers (AREA)
- Laminated Bodies (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2005800376305A CN101084467B (en) | 2004-11-03 | 2005-11-03 | Silicon containing tarc / barrier layer |
JP2007539334A JP4831777B2 (en) | 2004-11-03 | 2005-11-03 | Silicon-containing top antireflection coating material / barrier layer and method for forming the layer |
EP05825085A EP1820061B1 (en) | 2004-11-03 | 2005-11-03 | Method of forming a patterned material using a silicon containing tarc/barrier layer |
KR1020077010021A KR101143748B1 (en) | 2004-11-03 | 2005-11-03 | Silicon containing tarc/barrier layer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/980,365 | 2004-11-03 | ||
US10/980,365 US7320855B2 (en) | 2004-11-03 | 2004-11-03 | Silicon containing TARC/barrier layer |
Publications (1)
Publication Number | Publication Date |
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WO2006057782A1 true WO2006057782A1 (en) | 2006-06-01 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2005/039719 WO2006057782A1 (en) | 2004-11-03 | 2005-11-03 | Silicon containing tarc/barrier layer |
Country Status (7)
Country | Link |
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US (1) | US7320855B2 (en) |
EP (1) | EP1820061B1 (en) |
JP (1) | JP4831777B2 (en) |
KR (1) | KR101143748B1 (en) |
CN (1) | CN101084467B (en) |
TW (1) | TWI373484B (en) |
WO (1) | WO2006057782A1 (en) |
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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 |
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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 |
Also Published As
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EP1820061B1 (en) | 2013-01-02 |
KR20070083917A (en) | 2007-08-24 |
US20060093959A1 (en) | 2006-05-04 |
JP4831777B2 (en) | 2011-12-07 |
TWI373484B (en) | 2012-10-01 |
CN101084467A (en) | 2007-12-05 |
CN101084467B (en) | 2010-08-18 |
JP2008519297A (en) | 2008-06-05 |
US7320855B2 (en) | 2008-01-22 |
EP1820061A4 (en) | 2010-09-22 |
KR101143748B1 (en) | 2012-05-11 |
TW200615306A (en) | 2006-05-16 |
EP1820061A1 (en) | 2007-08-22 |
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