US20060063077A1 - Mask patterns including gel layers for semiconductor device fabrication and methods of forming the same - Google Patents

Mask patterns including gel layers for semiconductor device fabrication and methods of forming the same Download PDF

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Publication number
US20060063077A1
US20060063077A1 US11/233,406 US23340605A US2006063077A1 US 20060063077 A1 US20060063077 A1 US 20060063077A1 US 23340605 A US23340605 A US 23340605A US 2006063077 A1 US2006063077 A1 US 2006063077A1
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Prior art keywords
monomer unit
coating composition
polymer
resist pattern
proton
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Abandoned
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US11/233,406
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English (en)
Inventor
Mitsuhiro Hata
Hyun-woo Kim
Jung-Hwan Hah
Sang-gyun Woo
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Samsung Electronics Co Ltd
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Samsung Electronics Co Ltd
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Assigned to SAMSUNG ELECTRONICS CO., LTD. reassignment SAMSUNG ELECTRONICS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HAH, JUN-HWAN, HATA, MITSUHIRO, WOO, SANG-GYUN, KIM, HYUN-WOO
Publication of US20060063077A1 publication Critical patent/US20060063077A1/en
Priority to US12/496,185 priority Critical patent/US7985529B2/en
Abandoned legal-status Critical Current

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking
    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition

Definitions

  • the present invention relates to mask patterns. More particularly, the present invention relates to mask patterns for fabrication of a semiconductor device, methods of forming the same and methods of fabricating a semiconductor device using the mask patterns as etching masks.
  • a photoresist pattern is formed on a predetermined film to be etched for pattern formation, for example, a silicon film, a dielectric film, or a conductive film
  • the predetermined film may be etched by using the photoresist pattern as an etching mask to form a desired pattern.
  • CD critical dimension
  • short-wavelength exposure techniques such as E-beam lithography or a half-tone phase shift mask may be used.
  • Short-wavelength exposure based lithography may present difficulties in that this process can be material-dependent and uneconomical.
  • half-tone phase shift mask based lithography may pose limitations on mask formation technology and resolution, and thus, it may be difficult to form contact holes which are less than 150 nm in size.
  • Japanese Patent Laid-Open Publication No. 1989-307228 discusses a technique for forming a fine resist pattern in which a resist pattern formed by exposure and development of a resist film is thermally treated so that the profile shape of the resist pattern is altered.
  • Japanese Patent Laid-Open Publication Nos. 1993-241348, 1994-250379, 1998-73927, 1999-204399, 1999-283905, 1999-283910, 2000-58506, 2000-298356, 2001-66782, 2001-228616, 2001-19860, and 2001-109165 discuss a method of forming a fine resist pattern by a chemical treatment process.
  • Japanese Patent Laid-Open Publication No. 2001-228616 discusses a technique for decreasing a hole diameter and an isolation width of a resist pattern by increasing the thickness of the resist pattern.
  • the resist pattern that can serve as an acid donor is coated with a framing material that is capable of being crosslinked with the acid.
  • a crosslinked layer is formed as a layer covering the resist pattern at an interface between the resist pattern and the framing material layer.
  • Japanese Patent Laid-Open Publication Nos. 2003-107752, 2003-84448, 2003-84459, 2003-84460, 2003-142381, 2003-195527, 2003-202679, 2003-303757, and 2003-316026 discuss a composition for fine pattern formation and a pattern formation method.
  • Japanese Patent Laid-Open Publication No. 2003-202679 discusses a method of forming fine patterns using a coating agent.
  • the coating agent is coated on a substrate having photoresist patterns in order to decrease spacing between the photoresist patterns caused, at least in part, by the thermal shrinkage effect of the coating agent.
  • the mask pattern includes a resist pattern, and a gel layer formed on a surface of the resist pattern having a junction comprising hydrogen bonds between a proton donor polymer and a proton acceptor polymer.
  • the junction of the gel layer includes a plurality of regions capable of undergoing hydrogen bonding and wherein the proton donor polymer and the proton acceptor polymer are hydrogen bonded therebetween, and a defect region wherein the proton donor polymer and the proton acceptor polymer are not hydrogen-bonded therebetween so as to form a region lacking hydrogen bonding between the hydrogen-bonded regions.
  • Embodiments of the present invention further provide mask patterns for semiconductor device fabrication, having a construction suitable for forming a fine pattern at wavelengths above the wavelength limit of conventional lithography.
  • Embodiments of the present invention also provide methods of forming a mask pattern for semiconductor device fabrication.
  • methods of forming a mask pattern include forming a resist pattern on a substrate; and forming on a surface of the resist pattern, a gel layer having a junction formed by hydrogen bonding between a proton donor polymer and a proton acceptor polymer.
  • forming the gel layer includes preparing a coating composition comprising the proton donor polymer, the proton acceptor polymer, and/or a base; contacting the coating composition with the surface of the resist pattern; and heating the resist pattern to an extent wherein the coating composition is contacted with the surface of the resist pattern to diffuse an acid of the resist pattern into the coating composition.
  • methods of forming a mask pattern for semiconductor device fabrication enable the formation of a fine pattern with a smaller feature size while minimizing the transformation of the sidewall profile of opening or spaces and can ensure a sufficient resistance to dry etching.
  • Embodiments of the present invention further provide methods of fabricating a semiconductor device including forming an underlayer on a semiconductor substrate; forming a resist pattern having defined regions through which the underlayer is exposed to a first width; forming on a surface of the resist pattern a gel layer having a junction formed by hydrogen bonding between a proton donor polymer and a proton acceptor polymer; and etching the underlayer using the resist pattern and the gel layer as an etching mask.
  • FIG. 1 presents a flowchart that schematically illustrates a method of fabricating a semiconductor device according to some embodiments of the present invention
  • FIG. 2 presents a flowchart that schematically illustrates a method for preparing a coating composition for fine pattern formation which may be used in a method of fabricating a semiconductor device according to some embodiments of the present invention
  • FIGS. 3A through 3F present cross-sectional views that illustrate a method of fabricating a semiconductor device according to some embodiments of the present invention.
  • first, second, third etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings of the present invention.
  • spatially relative terms such as “beneath”, “below”, “lower”, “above”, “up”, “upper” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the figures. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, if the device in the figures is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” the other elements or features. Thus, the exemplary term “below” can encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein interpreted accordingly.
  • steps comprising the methods provided herein can be performed independently or at least two steps can be combined. Additionally, steps comprising the methods provided herein, when performed independently or combined, can be performed at the same temperature and/or atmospheric pressure or at different temperatures and/or atmospheric pressures without departing from the teachings of the present invention.
  • Embodiments of the invention are described herein with reference to cross-section illustrations that are schematic illustrations of idealized embodiments (and intermediate structures) of the invention. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments of the invention should not be construed as limited to the particular shapes of regions illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the actual shape of a region of a device and are not intended to limit the scope of the invention.
  • an underlayer to be etched is formed on a semiconductor substrate.
  • the underlayer may be formed of any suitable film material.
  • the underlayer may be a dielectric film such as a silicon film, an oxide film, a nitride film, an oxide-nitride film, a conductive film, a semiconductive film and/or a resist film.
  • the underlayer in order to form contact holes in the underlayer, is formed as a dielectric film.
  • a resist film is formed on the underlayer.
  • the resist film is subjected to exposure and development by conventional photolithography in order to obtain a resist pattern formed with openings through which the underlayer is exposed to a predetermined width.
  • a coating composition including a proton donor polymer, a proton acceptor polymer, and a base may be prepared.
  • at least one of these components included in the coating composition, i.e., the proton donor polymer, the proton acceptor polymer, and the base are water-soluble.
  • each of the proton donor polymer and the proton acceptor polymer may be used in an amount in a range of about of 0.1 to 5.0 wt %, and in some embodiments about 0.1% to 2.0 wt %, based on the total weight of the coating composition.
  • the proton donor polymer and the proton acceptor polymer may be mixed at a weight ratio in a range of about of 1:9 to 9:1.
  • the base may be used in an amount in a range of about of 0.1% to 5.0 wt %, and in some embodiments 0.2% to 1.0 wt %, based on the total weight of the coating composition.
  • the coating composition may include a surfactant or a thermal acid generator.
  • the proton donor polymer includes a monomer repeat unit having a —COOH or —COOR group, wherein R may be a substituted or unsubstituted hydrocarbon group of C 1 to C 20 .
  • the proton donor polymer includes a first repeat unit including at least one compound including an acrylic acid monomer unit represented by a compound of formula 1 and a maleic acid monomer unit represented by a compound of formula 2:
  • R 1 may be hydrogen or a lower alkyl group, such as methyl group
  • R 2 , R 3 , and R 4 are each independently hydrogen, a substituted or unsubstituted hydrocarbon group of C 1 to C 20 and/or a substituted or unsubstituted acid-labile group of C 1 to C 20 .
  • substituted or unsubstituted hydrocarbon groups of C 1 to C 20 include methyl and acetyl(isopropyl)(2-methyl-butan-3-on-2-yl).
  • Examples of a suitable acid-labile group include t-butyl, isonorbonyl, 2-metyl-2-adamantyl, 2-ethyl-2-adamantyl, 3-tetrahydrofuranyl, 3-oxocyclohexyl, ⁇ -butyllactone-3-yl, mavaloniclactone, ⁇ -butyrolactone-2-yl, 3-methyl- ⁇ -butyrolactone-3-yl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 2,3-propylenecarbonate-1-yl, 1-methoxyethyl, 1-ethoxyethyl, 1-(2-methoxyethoxy)ethyl, 1-(2-acetoxyethoxy)ethyl, t-buthoxycarbonylmethyl, methoxymethyl, ethoxymethyl, trimethoxysilyl, and/or triethoxysilyl.
  • At least one of R 2 , R 3 , and R 4 of the proton donor polymer may be a group that includes silicon.
  • An exemplary group including silicon to be used herein is a trimethoxysilyl group and/or a triethoxysilyl group.
  • the first repeat unit of the proton donor polymer may be a homopolymer including an acrylic acid monomer unit of formula 1 alone or a copolymer including an acrylic acid monomer unit of formula 1 and the maleic acid monomer unit of formula 2.
  • the proton donor polymer may further include a second repeat unit Z 1 including a monomer unit having a structure that is different from the acrylic acid monomer unit of formula 1 and the maleic acid monomer unit of formula 2.
  • the second repeat unit Z 1 may include at least one compound including an acrylamide monomer unit, a vinyl monomer unit, an alkyleneglycol monomer unit, an anhydrous maleic acid monomer unit, an ethyleneimine monomer unit, an oxazoline monomer unit, an acrylonitrile monomer unit, an allylamide monomer unit, a 3,4-dihydropyrane monomer unit, and a 2,3-dihydrofuran monomer unit.
  • the proton donor polymer may be a copolymer, a terpolymer, a tetrapolymer, or the like according to the second repeat unit Z 1 .
  • the second repeat unit Z 1 of the proton donor polymer may include two or more different monomer units.
  • Examples of the acrylamide monomer unit of the second repeat unit Z 1 include N,N-dimethylacrylamide, methacrylamide, N,N-dimethylmethacrylamide, N-isopropylacrylamide, aminopropylacrylamide, aminopropylmethacrylamide, N,N-dimethylaminopropylacrylamide, N,N-dimethylaminopropylmethacrylamide, N-acryloylmorpholine, N-methylacrylamide, diacetonacrylamide, N,N-dimethylaminoethylmethacrylate, N,N-diethylaminoethylmethacrylate, and N,N-dimethylaminoethylacrylate.
  • Examples of the vinyl monomer unit of the second repeat unit Z 1 include vinylalcohol, vinylacetate, vinylacetal, methylvinylether, ethylvinylether, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazolidinone, and vinylsulfonic acid.
  • alkyleneglycol monomer unit comprising the second repeat unit Z 1 examples include ethyleneglycol and propyleneglycol.
  • the second repeat unit Z 1 may include a hydrophilic monomer unit alone or in combination of a hydrophobic monomer unit.
  • the first repeat unit of the proton donor polymer is present in an amount of about 3% to 90%, and in some embodiments, about 5% to 50%, based on the total number of repeat units.
  • the proton donor polymer has a weight average molecular weight in a range of about 1,000 to 100,000 daltons, and in some embodiments, about 2,000 to 50,000 daltons.
  • the proton acceptor polymer includes a monomer repeat unit including an amido group.
  • the proton acceptor polymer may include a first repeat unit including a vinyl monomer unit represented by the following formula 3:
  • R 5 may be hydrogen or a lower alkyl group, such as a methyl group
  • R 6 and R 7 are each independently a hydrogen atom or an alkyl group of C 1 to C 5 , R 6 and R 7 can be connected in the form of —R 6 —R 7 .
  • the proton acceptor polymer may further include a second repeat unit Z 2 including a monomer unit including a structure that is different from the vinyl monomer unit of the formula 3.
  • the second repeat unit Z 2 may include at least one compound including an acrylic monomer unit, a vinyl monomer unit, an alkyleneglycol monomer unit, an ethyleneimine monomer unit, an oxazoline monomer unit, an acrylonitrile monomer unit, an allylamide monomer unit, a 3,4-dihydropyrane monomer unit, and a 2,3-dihydrofuran monomer unit.
  • the proton acceptor polymer may be a copolymer, a terpolymer, a tetrapolymer, or the like according to the second repeat unit Z 2 .
  • the second repeat unit Z 2 of the proton acceptor polymer may include two or more different monomer units.
  • acrylic monomer unit of the second repeat unit Z 2 examples include acrylate, methacrylate, maleic acid, anhydrous maleic acid, N,N-dimethylacrylamide, methacrylamide, N, N-dimethylmethacrylamide, N-isopropylacrylamide, aminopropylacrylamide, aminopropylmethacrylamide, N,N-dimethylaminopropylacrylamide, N,N-dimethylaminopropylmethacrylamide, N-acryloylmorpholine, N-methylacrylamide, diacetonacrylamide, N,N-dimethylaminoethylmethacrylate, N,N-diethylaminoethylmethacrylate, and N,N-dimethylaminoethylacrylate.
  • Examples of the vinyl monomer unit of the second repeat unit Z 2 include vinylalcohol, vinylacetate, vinylacetal, methylvinylether, ethylvinylether, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazolidinone, and vinylsulfonic acid.
  • alkyleneglycol monomer unit of the second repeat unit Z 2 examples include ethyleneglycol and propyleneglycol.
  • the second repeat unit Z 2 may include a hydrophilic monomer unit alone or in combination with a hydrophobic monomer unit.
  • formula 3 in some embodiments when R 6 and R 7 are connected in the form of —R 6 —R 7 —, formula 3 may be replaced with a structure represented by formula 4:
  • n is an integer from 1 to 8. In some embodiments, n is 1, 2, 3, 4, 5, 6, 7 or 8.
  • a representative example of the proton acceptor polymer including a repeat unit of formula 4 is a polymer including a vinyl pyrrolidone monomer unit or a caprolactam monomer unit.
  • the proton acceptor polymer may include a first repeat unit including a vinyl monomer unit represented by the following formula 5:
  • R 8 is hydrogen or a lower alkyl group, such as methyl group
  • R 9 and R 10 are each independently a hydrogen atom, or a lower slkyl group, such as a methyl group, an n-propyl group, or an i-propyl group.
  • the proton acceptor polymer may further include a second repeat unit Z 3 to be copolymerized with the vinyl monomer unit of formula 5.
  • the above description of the second repeat unit Z 2 can also be applied to the second repeat unit Z 3 .
  • the first repeat unit of the proton acceptor polymer is present in an amount in a range of about 3% to 100%, and in some embodiments, about 50% to 100%, based on the total number of repeat units.
  • the proton acceptor polymer has a weight average molecular weight in a range of about 1,000 to 100,000 daltons, and in some embodiments, about 2,000 to 50,000 daltons.
  • the base may be used to reduce or prevent formation of a water-insoluble interpolymer complex by formation of a hydrogen bond between the proton donor polymer and the proton acceptor polymer in the coating composition.
  • the base allows the proton donor polymer to include a defect area including a —COO ⁇ group, which may prevent formation of an interpolymer complex between the proton donor polymer and the proton acceptor polymer. Therefore, the coating composition can be maintained as a clear aqueous solution.
  • the defect area of the proton donor polymer may also be provided by a protecting group or an acid-labile group which may be present in the proton donor polymer, in addition to the base. That is, a —COOR protecting group (wherein R is a substituted or unsubstituted hydrocarbon group of C 1 to C 20 or a substituted or unsubstituted acid-labile group of C 1 to C 20 ) which may be present in the proton donor polymer can also constitute the defect area of the proton donor polymer. Therefore, even when the coating composition includes lower amounts of the base, formation of an interpolymer complex between the proton donor polymer and the proton acceptor polymer may be prevented and the coating composition may be maintained as a clear aqueous solution.
  • the proton donor polymer including a protecting group is used in an amount sufficient to limit, if not exclude, the use of the base.
  • the base is used in an amount in a range of about 0.1 to 5.0 wt %, and in some embodiments, about 0.2 to 1.0 wt %, based on the total weight of the coating composition.
  • the base is a material with a boiling point of at least about 140° C.
  • An exemplary base suitable to be used in the coating composition includes an amine such as monoethanolamine and triethanolamine, tetramethylammonium hydroxide (TMAH), or tetraethylammonium hydroxide.
  • the coating composition may further include a trace amount of a protonic acid.
  • the protonic acid may serve as a further acid in addition to an acid to be diffused from the resist pattern, thereby facilitating gelation of the coating composition.
  • the acid is used in an amount in a range of about 0.1 to 10 wt %, and, in some embodiments, about 0.2 to 1.0 wt %, based on the total weight of the coating composition.
  • the acid may be selected from various materials.
  • the acid may be replaced with a compound generating an acid when subjected to heat.
  • an exemplary acid suitable to be used in the coating composition is p-toluenesulfonic acid, trifluoroacetic acid, or dodecylbenzenesulfonic acid.
  • the surfactant may be used to provide desirable coverage characteristics when the above-described resist pattern is coated with the coating composition.
  • the surfactant may be used in an amount in a range of about 0.01 to 0.5 wt %, based on the total weight of the coating composition.
  • the surfactant may be selected from various materials.
  • the surfactant may be a commercially available surfactant such as “Zonyl-FSN” (DuPont), “PolyFox(TM)” (OMNOVA Solutions Inc.), “FluoradTM” (3M), “NONIPORUTM” (SANYOKASEI), “MEGAFACETM” (Dainippon Ink & Chemicals), or a mixture thereof.
  • the coating composition may further include an additive such as alcohol, ether, primary amine, secondary amine, tertiary amine, or an organic salt.
  • the additive may include R 11 —OH, R 12 —O—R 13 , N(H) 2 R 14 , NHR 15 R 16 , NR 17 R 18 R 19 , (R 20 ) 4 NCO 3 R 21 , and (R 22 ) 4 NCO 2 R 23 , wherein R 11 through R 23 are each independently a straight-chain alkyl, a branched-chain alkyl, a cyclic alkyl, an aromatic ring, an alkyl substituted aromatic ring, or —(CH 2 ) n —, wherein n is an integer from 1 to 8, and thus, n may be 1, 2, 3, 4, 5, 6, 7 or 8.
  • a solvent used in the coating composition may include deionized water or a mixture of deionized water and an organic solvent.
  • the solvent is deionized water.
  • the organic solvent may be used in an amount in a range of about 0% to 20 wt %, based on the total weight of the coating composition.
  • the organic solvent may include alcohols, nitrites, ketones, esters, lactate esters, aromatic hydrocarbons, and amides.
  • the contents of the acid and the base may be adjusted so that the lower critical solution temperature (LCST) of the coating composition is in a range of about 30° to 70°.
  • LCST lower critical solution temperature
  • the coating polymer including the proton donor polymer and the proton acceptor polymer may be contacted with a surface of the resist pattern formed as described above. Suitable techniques for this process include, spin coating, puddling, dipping, or spraying. In some embodiments, spin coating is employed.
  • the time for the contacting step may be set to any time period in a range of about 30 to 90 seconds.
  • the coating composition may be maintained at a temperature in a range of about 10° to 30°, and in some embodiments, at a room temperature.
  • the contacting step is performed at the same temperature in which the coating composition is maintained.
  • the semiconductor substrate may be rotated or fixed according to a contact method.
  • a contact method for example, in the case of spin coating, the semiconductor substrate may be rotated about its center at a predetermined speed, for example 500 to 3,000 rpm. In order to perform uniform coating while limiting pattern defects, a rotation speed of 1,500 to 2,000 rpm may be employed.
  • puddling or spraying the semiconductor substrate is fixed without moving or rotating.
  • the semiconductor substrate may be heated in a state wherein the coating composition is contacted with the surface of the resist pattern to diffuse an acid of the resist pattern into the coating composition.
  • heating is performed at a temperature in a range of about 120° to 170° for a period of time in a range of about 60 to 90 seconds.
  • a gel layer including a zipper type junction zone characterized by hydrogen bonding between the proton donor polymer and the proton acceptor polymer.
  • the gel layer is water-insoluble.
  • the zipper type junction zone of the gel layer may include a plurality of hydrogen bond areas in which the proton donor polymer and the proton acceptor polymer may be hydrogen-bonded and a defect area in which the proton donor polymer and the proton acceptor polymer are not hydrogen-bonded therebetween so as to form a loop between the hydrogen bond areas.
  • the proton donor polymer has a —COO ⁇ group or a —COOR group wherein R may be a substituted or unsubstituted hydrocarbon group of C 1 to C 20 or a substituted or unsubstituted acid-labile group of C 1 to C 20 .
  • R may also be a group including silicon.
  • a water-soluble coating composition remaining around the gel layer formed on the surface of the resist pattern may be removed.
  • the coating composition may be removed by rinsing with deionized water.
  • rinsing may be performed by rotating the semiconductor substrate at a rate in a range of about 500 to 4,000 rpm for a period of time in a range of about 30 to 90 seconds.
  • the water-insoluble gel layer when the water-soluble coating composition is removed, the water-insoluble gel layer may remain on the surface of the resist pattern.
  • the gel layer may decrease the width of the underlayer exposed through the openings of the resist pattern.
  • the underlayer formed on the semiconductor substrate may be etched by using the resist pattern and the gel layer as an etching mask. As a result, a fine pattern above a wavelength limit of lithography may be obtained.
  • FIG. 2 presents a flowchart that schematically illustrates a method of preparing a coating composition for fine pattern formation according to some embodiments of the present invention as shown in blocks 21 , 22 , 23 , 24 and 25 .
  • a first aqueous solution including a proton acceptor polymer and a base is prepared.
  • the first aqueous solution includes a first solvent, in addition to the proton acceptor polymer and the base.
  • the first solvent may be deionized water or a mixture of deionized water and an organic solvent.
  • the first aqueous solution may further include a surfactant and an additive.
  • the base of the first aqueous solution may be limited or excluded according to the type of proton donor polymer used, i.e., as the proton donor polymer has a larger number of protecting groups, the amount of the base can be decreased.
  • the proton acceptor polymer, the base, the surfactant, the additive, and the first solvent are described above.
  • a second aqueous solution including the proton donor polymer is prepared.
  • the second aqueous solution includes a second solvent, in addition to the proton donor polymer.
  • the second solvent may be deionized water or a mixture of deionized water and an organic solvent.
  • the proton donor polymer and the second solvent are described above.
  • a mixed solution of the first aqueous solution and the second aqueous solution may be prepared. More specifically, the second aqueous solution may be added dropwise to the first aqueous solution. In some embodiments, the second aqueous solution may be added dropwise to the first aqueous solution with stirring to prevent the formation of an interpolymer complex in the mixed solution. Addition of the first aqueous solution to the second aqueous solution may produce varying amounts of a sparsely soluble precipitate or hydrogel.
  • the mixed solution of the first aqueous solution and the second aqueous solution may be ultrasonically treated in order to disperse trace precipitates or hydrogels that may exist in the mixed solution.
  • the mixed solution may be filtered to obtain a coating composition as a clear solution.
  • the coating composition thus obtained may have LCST in a range of about 30° C. to 70° C. according to its constitutional components.
  • the coating composition includes a proton donor polymer, a proton acceptor polymer, and a base, i.e., when an acid is not included in the coating composition, the coating composition may have a low LCST. Therefore, even when the temperature of the coating composition is slightly increased, the coating composition may turn cloudy.
  • the proton donor polymer and the proton acceptor polymer in the coating composition may interact with each other at a temperature greater than room temperature, thereby forming a water-insoluble interpolymer complex. Accordingly, it is not desirable to maintain the coating composition at a high temperature because it may become difficult to disperse precipitates or hydrogels in the coating composition.
  • LCST of the coating composition may be controlled by adjusting the contents of the acid or the base in the mixed solution.
  • FIGS. 3A through 3F present sequential sectional views that illustrate a method of fabricating a semiconductor device according to some embodiments of the present invention.
  • an underlayer 110 to be etched to form a predetermined pattern for example contact holes or trenches, may be formed on a semiconductor substrate 100 .
  • the underlayer 110 may be a dielectric film, a conductive film, a semiconductive film, or a resist film.
  • a resist pattern 120 may be formed on the underlayer 110 .
  • the resist pattern 120 may be formed with openings through which an upper surface of the underlayer 110 may be exposed to a first width d 1 .
  • the resist pattern 120 may be formed with a plurality of openings defining a hole pattern or a plurality of lines defining a line and space pattern.
  • the first width d 1 corresponds to the width of each space between the lines.
  • the resist pattern 120 may include a material including a Novolak resin and a diazonaphthoquinone (DNQ)-based compound.
  • the resist pattern 120 may also be formed using a common chemically amplified resist composition including a photo-acid generator (PAG).
  • PAG photo-acid generator
  • the resist pattern 120 may be formed using a resist composition for g-line, a resist composition for i-line, a resist composition for KrF excimer laser (248 nm), a resist composition for ArF excimer laser (193 nm), a resist composition for F 2 excimer laser (157 nm), or a resist composition for e-beams.
  • the resist pattern 120 may also be formed using a positive-type resist composition or a negative-type resist composition.
  • a coating composition 130 may be contacted with a surface of the resist pattern 120 .
  • the coating composition 130 may be applied on the resist pattern 120 while rotating the semiconductor substrate 100 at a rate in a range of about 500 to 3,000 rpm for a period of time in a range of about 30 to 90 seconds.
  • the semiconductor substrate 100 may be rotated at a rate in a range of about 1,500 to 2,000 rpm to uniformly coat the coating composition 130 on the semiconductor substrate 100 while causing minimal to no pattern defects.
  • the semiconductor substrate 100 may be heated to a state wherein the coating composition 130 may be contacted with the surface of the resist pattern 120 to diffuse an acid of the resist pattern 120 into the coating composition 130 .
  • a gel layer 132 may be formed on the surface of the resist pattern 120 . Heating may be performed at a temperature in a range of about 120° C. to 170° C.
  • the gel layer 132 thus formed may be water-insoluble.
  • the resist pattern 120 and the gel layer 132 may constitute a mask pattern to be used as an etching mask upon etching the underlayer 110 .
  • the coating composition 130 remaining around the gel layer 132 may be removed. Since the coating composition 130 may be water-soluble, it may be more readily removed by rinsing with deionized water. As a result, the underlayer 110 may be exposed to a second width d 2 which may be smaller than the first width d 1 through the openings of the resist pattern 120 . Accordingly, an exposed area of the underlayer 110 may be defined by the gel layer 132 formed on the surface of the resist pattern 120 .
  • the underlayer 110 may be dry-etched by using the resist pattern 120 and the gel layer 132 as an etching mask to form an underlayer pattern 110 a.
  • the mask pattern composed of the resist pattern 120 and the gel layer 132 may be removed.
  • the gel layer 132 may be formed on the surface of the resist pattern 120 to reduce the sizes of openings of a mask pattern.
  • the gel layer 132 may be a water-insoluble film that has a zipper type junction zone formed by a hydrogen bond between a proton donor polymer and a proton acceptor polymer.
  • the gel layer 132 formed on the surface of the resist pattern 120 may form a mask pattern with small-sized openings above the wavelength limit of photolithography technology. Furthermore, a vertical sidewall profile of a mask pattern may be maintained unchanged or with minimal change.
  • An antireflective film (DUV-30, Nissan Chemical Industries, Ltd.) was formed to a thickness of about 360 ⁇ on an 8-inch bare silicon wafer.
  • a photoresist for ArF (SAIL-G24c, ShinEtsu Chemical Co. Ltd) was subsequently spin-coated on the antireflective film followed by baking at about 105° C. for about 60 seconds to form a resist film with a thickness of about 3,000 ⁇ .
  • the resist film was exposed to light by an ArF (193 nm) stepper followed by post-exposure baking (PEB) at about 105° C. for about 60 seconds.
  • PEB post-exposure baking
  • the wafer was developed with a 2.38 wt % tetramethylammonium hydroxide (TMAH) solution to form, on the wafer, a resist pattern having a plurality of openings.
  • the resist pattern had an isolated hole pattern (hereinafter, referred to as “i-hole pattern”) with a diameter of 129.7 nm and a dense hole pattern (hereinafter, referred to as “d-hole pattern”) with a diameter of 138.0 nm selected at a center portion of a hole array in which a plurality of holes were patterned at a pitch of 240 nm.
  • i-hole pattern isolated hole pattern
  • d-hole pattern dense hole pattern
  • Poly(acrylic acid-co-maleic acid) (720 mg) and t-butylacetoacetate (4.7 g) were mixed, stirred at 62° C. for 7 hours, and subjected to precipitation with excess hexane. A supernatant was decanted, and the remaining solid was purified with THF (tetrahydrofuran)/hexane and dried under vacuum at 30° C. overnight to provide a partially t-butyl protected poly(acrylic acid-co-maleic acid) (640 mg) as a white powder.
  • THF tetrahydrofuran
  • a solution of 22 mg of triethanolamine (TEA) in 1,978 mg H 2 O (deionized water), a solution of 2.0 mg of Zonyl FSN in 198 mg H 2 O, and 1.8 g H 2 O were added to a solution of 100 mg of poly(vinylpyrrolidone) in 900 mg H 2 O to obtain a first aqueous solution.
  • a second aqueous solution of 100 mg of the partially t-butyl protected poly(acrylic acid-co-maleic acid) obtained as described above in 900 mg H 2 O was added dropwise to the first aqueous solution with vigorously stirring. Small quantities of hydrogels created during the dropwise addition were dispersed by ultrasonic treatment. The resultant solution was filtered to give a clean coating composition.
  • the LCST (lower critical solution temperature) of the coating composition was about 45° C.
  • TEA which was a base used to obtain a clear aqueous solution, was used in an amount of 11 wt %, based on the total amount of a resin used.
  • the coating composition obtained using methods described above was spin-coated on the resist pattern formed according to methods described above to form a uniform film.
  • the uniform film was baked at about 145° C. for about 60 seconds and rinsed with deionized water. As a result, a water-insoluble gel layer was uniformly formed on the surface of the resist pattern.
  • the i-hole pattern and the d-hole pattern had a reduced diameter of 59.1 nm and 115.7 nm, respectively.
  • a solution of 35 mg of TEA in 3,465 mg H 2 O, a solution of 4.0 mg of Zonyl FSN in 396 mg H 2 O, and 100 mg H 2 O were added to a solution of 100 mg of poly(vinylpyrrolidone) in 900 mg H 2 O to obtain a first aqueous solution.
  • the resultant solution was filtered to provide a clean coating composition.
  • the LCST of the coating composition was about 50° C.
  • TEA was used in an amount of 17 wt %, based on the total amount of a resin used.
  • Such an increase in the amount of the base used to obtain a clear aqueous solution in this Example, relative to the amount of the base used in Example 1, can be explained by use of the unprotected poly(acrylic acid-co-maleic acid).
  • the coating composition obtained according to methods described above was spin-coated on a resist pattern formed in the same manner as described in Example 1 to form a uniform film.
  • the uniform film was baked at about 145° C. for about 60 seconds and rinsed with deionized water. As a result, a water-insoluble gel layer was uniformly formed on the surface of the resist pattern.
  • the i-hole pattern and the d-hole pattern had a reduced diameter of 73.8 nm and 115.3 nm, respectively.
  • a resist pattern was formed in the same manner as described in Example 1 except that PEB was performed at 115° C. for about 60 seconds.
  • the resist pattern included an i-hole pattern with a diameter of 174.8 nm and a d-hole pattern with a diameter of 134.7 nm.
  • Poly(acrylic acid-co-maleic acid) (370 mg), N,N′-dicyclohexylcarbodiimide (10 mg), 4-(dimethylamino)pyridine (3.0 mg), and t-BuOH (2.0 g) were stirred at 23° C. for 4 hours and subjected to precipitation with excess hexane. A supernatant was decanted and the remaining solid was dried under vacuum at 30° C. overnight to provide 10% t-butyl protected poly(acrylic acid-co-maleic acid) (319 mg) as a white solid.
  • TMAH tetramethylammonium hydroxide
  • a solution of 1.0 mg of Zonyl FSN in 99 mg H 2 O, and 1.7 g H 2 O were added to a solution of 50 mg of poly(vinylpyrrolidone) in 450 mg H 2 O to obtain a first aqueous solution.
  • a second aqueous solution of 50 mg of the 10% t-butyl protected poly(acrylic acid-co-maleic acid), obtained as described above, in 450 mg H 2 O was added dropwise to the first aqueous solution with vigorous stirring. The resultant solution was filtered to provide a clean coating composition.
  • the amount of TMAH used to obtain a clear aqueous solution was 5.3 wt %, based on the total amount of a resin used.
  • the coating composition obtained in operation 3 - 3 was spin-coated on the resist pattern formed in operation 3 - 1 to form a uniform film.
  • the uniform film was baked at about 145° C. for about 60 seconds and rinsed with deionized water. As a result, a water-insoluble gel layer was uniformly formed on the surface of the resist pattern.
  • the i-hole pattern and the d-hole pattern had a reduced diameter of 160.1 nm and 122.7 nm, respectively.
  • a solution of 40 mg of TMAH in 1,660 mg H 2 O, a solution of 2.0 mg of Zonyl FSN in 198 mg H 2 O, and 6.1 g H 2 O were added to a solution of 200 mg of poly(vinylpyrrolidone) in 1,800 mg H 2 O to obtain a first aqueous solution.
  • TMAH was used in an amount of 11 wt %, based on the total amount of a resin used.
  • Such an increase of the amount of the base used to obtain a clear aqueous solution in this Example, relative to the amount of the base used in Example 3, can be explained by use of the unprotected poly(acrylic acid-co-maleic acid).
  • the coating composition obtained according to methods described above was spin-coated on a resist pattern formed in the same manner as described in Example 3 to form a uniform film.
  • the uniform film was baked at about 145° C. for about 60 seconds and rinsed with deionized water. As a result, no chemical attachment layers on the surface of the resist pattern were observed.
  • a gel layer with a zipper type junction zone formed by a hydrogen bond between a proton donor polymer and a proton acceptor polymer may be formed on the surface of a resist pattern to obtain a mask pattern formed with small-sized openings beyond the wavelength limit of conventional photolithography technology.
  • the mask pattern including the resist pattern and the gel layer formed on the resist pattern may present a vertical sidewall profile.
  • use of a proton donor polymer with a silicon-containing protecting group may increase the silicon content in the mask pattern, thereby enhancing a resistance to dry etching.

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