WO2012005418A1 - Composé contenant un noyau aromatique pour une sous-couche de réserve, composition de sous-couche de réserve le contenant et procédé de formation de motif de dispositif au moyen de cette composition - Google Patents

Composé contenant un noyau aromatique pour une sous-couche de réserve, composition de sous-couche de réserve le contenant et procédé de formation de motif de dispositif au moyen de cette composition Download PDF

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WO2012005418A1
WO2012005418A1 PCT/KR2010/008854 KR2010008854W WO2012005418A1 WO 2012005418 A1 WO2012005418 A1 WO 2012005418A1 KR 2010008854 W KR2010008854 W KR 2010008854W WO 2012005418 A1 WO2012005418 A1 WO 2012005418A1
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formula
group
underlayer film
resist underlayer
unsubstituted
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PCT/KR2010/008854
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English (en)
Korean (ko)
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오승배
김민수
송지윤
전환승
조성욱
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제일모직 주식회사
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Publication of WO2012005418A1 publication Critical patent/WO2012005418A1/fr

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    • 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
    • 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
    • G03F7/0041—Photosensitive materials providing an etching agent upon exposure
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • 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
    • 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

Definitions

  • the present disclosure relates to an aromatic ring-containing compound for resist underlayer films, a resist underlayer film composition comprising the compound, and a pattern forming method of a device using the same.
  • a typical lithographic process first applies a resist to an underlying material and then exposes it to radiation to form a resist layer.
  • the resist layer is then developed with a developer to form a patterned resist layer, and the material in the openings of the patterned resist layer is etched to transfer the pattern to the underlying material. After the transfer is completed, the remaining resist layer is removed.
  • the resist may not have sufficient resistance to an etching step to effectively transfer a predetermined pattern to the underlying material. Therefore, when an ultra thin resist layer using an extremely thin resist material is required, when the substrate to be etched is thick, or when an etching depth is required deeply, it is necessary to use a specific etchant for a given underlayer material. In some cases, a resist underlayer film has been used.
  • the resist underlayer film serves as an intermediate layer between the resist layer and the substrate to be patterned, and serves to transfer the pattern of the patterned resist layer to the underlayer material, and thus must withstand the etching process required to transfer the pattern.
  • underlayer film compositions that provide adequate shelf life and avoid interfering interactions with the resist layer (e.g., contaminating the resist or substrate by an acid catalyst included in the underlayer film composition)
  • underlayer film composition having predetermined optical properties for radiation of shorter wavelengths (eg, 157 nm, 193 nm or 248 nm).
  • One aspect of the present invention is to provide an aromatic ring-containing compound for resist underlayer films having excellent optical properties, mechanical properties, and etch selectivity properties, which can be applied using a spin-on application technique. will be.
  • Another aspect of the present invention is to provide a resist underlayer film composition including the compound is excellent in the etching selectivity to provide sufficient resistance to multiple etching, and does not use the acid catalyst, there is no contamination problem due to the use of the acid catalyst It is.
  • Another aspect of the present invention is to provide a method of forming a device pattern using the resist underlayer film composition.
  • One aspect of the present invention is to provide an aromatic ring-containing compound comprising a repeating unit represented by the following formula 1-1 and a repeating unit represented by the following formula 1-2.
  • m is in the range 1 ⁇ m ⁇ 190.
  • p is an integer of 1 or 2
  • Ar is an aromatic ring group
  • X is a hydroxy group (-OH), a substituted or unsubstituted C1 to C10 alkoxy group or a substituted or unsubstituted C6 to C30 aryl oxy group,
  • R a is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C10 alkenyl group, or a halogen group to be.
  • n is in the range of 1 ⁇ n ⁇ 190
  • R b and R c are the same as or different from each other, and are hydrogen, a substituted or unsubstituted C3 to C8 cycloalkyl group, or a substituted or unsubstituted C6 to C30 aryl group, provided that R b and R c are not simultaneously hydrogen.
  • n may be 1 ⁇ n ⁇ 40 or n may be in a range of 1 ⁇ n ⁇ 20.
  • the weight average molecular weight of the aromatic ring-containing compound may be 2,000 to 10,000.
  • Another aspect of the present invention provides a resist underlayer film composition
  • a resist underlayer film composition comprising an aromatic ring-containing compound and an organic solvent comprising a repeating unit represented by Chemical Formula 1-1 and a repeating unit represented by Chemical Formula 1-2.
  • the resist underlayer film composition may further include a surfactant or a crosslinking component.
  • Another aspect of the present invention provides a method of manufacturing a semiconductor device, the method comprising: (a) providing a material layer on a substrate; (b) forming an underlayer film on the material layer using the resist underlayer film composition; (c) forming a resist layer on the underlayer film; (d) exposing the substrate on which the resist layer is formed; (e) developing the exposed substrate; And (f) etching the developed substrate.
  • a step of forming a silicon-containing resist underlayer film may be further performed before the step (c) of forming a resist layer.
  • a step of forming a bottom anti-reflective coating (BARC) may be further performed before the forming of the (c) resist layer.
  • the aromatic ring containing compound has very good optical properties, mechanical properties and etching selectivity properties.
  • the underlayer film composition including the compound may be applied to a substrate by a spin-on coating technique, is useful for a shorter wavelength lithographic process, and there is no problem of contamination by an acid catalyst.
  • the composition containing the compound may minimize the reflectivity between the resist and the material layer by having a refractive index and absorbance of the range useful as an antireflection film in the DUV (Deep UV) region, such as the ArF (193nm) wavelength region when forming the film.
  • a refractive index and absorbance of the range useful as an antireflection film in the DUV (Deep UV) region such as the ArF (193nm) wavelength region when forming the film.
  • the etching selectivity is very high compared to the existing materials, and the resistance to multiple etching is sufficient, so that the etch profile of the underlayer film, which is an image to be transferred to the lower layer, is very good.
  • substituted means substituted with a hydroxy group, a halogen, a C1 to C10 alkyl group, a C5 to C20 aryl group or a C2 to C10 alkenyl group.
  • the aromatic ring group means a functional group in the form in which electrons are delocalized or resonated, and means an aryl group, a heteroaryl group, and the like.
  • the heteroaryl group means containing 1 to 3 heteroatoms of N, O, S or P in the ring.
  • the alkyl group is a C1 to C10 alkyl group
  • the aryl group is a C6 to C20 aryl group
  • the alkenyl group is a C2 to C10 alkenyl group such as a vinyl group or an allyl group.
  • an aromatic ring-containing compound for a resist underlayer film including a repeating unit represented by the following Formula 1-1 and a repeating unit represented by the following Formula 1-2 is provided.
  • m is in the range 1 ⁇ m ⁇ 190.
  • p is an integer of 1 or 2
  • Ar is an aromatic ring group
  • X is a hydroxy group (-OH), a substituted or unsubstituted C1 to C10 alkoxy group or a substituted or unsubstituted C6 to C30 aryl oxy group,
  • Ra is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C10 alkenyl group, or a halogen group .
  • n is in the range of 1 ⁇ n ⁇ 190
  • R b and R c are the same as or different from each other, and are hydrogen, a substituted or unsubstituted C3 to C8 cycloalkyl group, or a substituted or unsubstituted C6 to C30 aryl group, provided that R b and R c are not simultaneously hydrogen.
  • An aromatic ring-containing compound comprising a repeating unit represented by Chemical Formula 1-1 and a repeating unit represented by Chemical Formula 1-2 has an aromatic ring having strong absorption in a short wavelength region (particularly, 193 nm and 248 nm). Since it is included in the skeleton portion of the compound, it can be used as an antireflection film.
  • the etching selectivity is excellent, and the resistance to multiple etching, the heat resistance and the like are excellent.
  • n may be 1 ⁇ n ⁇ 40 or n may be in a range of 1 ⁇ n ⁇ 20.
  • the aromatic ring group (Ar) in Chemical Formula 1-1 may be selected from the group consisting of the following Chemical Formulas 2 to 13.
  • R 1 to R 44 are each independently hydrogen, a hydroxy group, an alkyl group, an aryl group, an alkenyl group or a halogen group,
  • h 1 to h 44 are each independently 0 to k-2, where k corresponds to the total number of H that may be present in each aromatic ring.
  • R a is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C10 alkenyl group or halogen group.
  • R a may be an aryl group represented by Formulas 14 to 25.
  • Y 1 to Y 44 are each independently hydrogen, a hydroxy group, an alkyl group, an aryl group, an alkenyl group or a halogen group,
  • r1 to r44 are each independently 0 to k-1, where k corresponds to the total number of H that may be present in each aromatic ring.
  • R a in Formula 1-1 and R c in Formula 1-2 are the same as or different from each other, and are hydrogen, a substituted or unsubstituted C3 to C8 cycloalkyl group, or a substituted or unsubstituted C6 to C30 aryl group, provided R a and R c are not simultaneously hydrogen.
  • R a in Formula 1-1 and R c in Formula 1-2 may be aryl groups represented by Formulas 26 to 37.
  • Z 1 to Z 44 are each independently hydrogen, a hydroxy group, an alkyl group, an aryl group, an alkenyl group or a halogen group,
  • s1 to s44 are each independently 0 to k-1, where k corresponds to the total number of H that may be present in each aromatic ring.
  • the weight average molecular weight of the aromatic ring-containing compound may be about 2,000 to 10,000. When the weight average molecular weight of the aromatic ring-containing compound is included in the above range, the desired coating thickness can be realized or a good thin film can be formed .
  • Another embodiment of the present invention provides an underlayer film composition comprising an aromatic ring-containing compound.
  • the aromatic ring-containing compound is a compound including a repeating unit represented by Formula 1-1 and a repeating unit represented by Formula 1-2.
  • the resist underlayer film composition includes an organic solvent. It will not specifically limit, if it is an organic solvent which has sufficient solubility with respect to the said polymer as this organic solvent.
  • organic solvents include propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), cyclohexanone and ethyl lactate. lactate), gamma-butyrolactone (GBL), acetyl acetone, and the like.
  • the content of the aromatic ring-containing compound may be 1 to 20% by weight, more preferably 3 to 10% by weight.
  • the composition can be appropriately adjusted to the desired coating thickness when forming the underlayer film.
  • the content of the organic solvent may be the remainder, that is, 80 to 99% by weight, when the content of the organic solvent is included in the above range, by applying the composition to adjust the desired coating thickness to the desired coating thickness when forming the underlayer film Can be.
  • the underlayer film composition according to the embodiment of the present invention may further include an acid catalyst.
  • the content of the acid catalyst may be 0.001 to 0.05 parts by weight based on 100 parts by weight of the underlayer film composition.
  • the acid catalyst include p-toluenesulfonic acid mono hydrate, pyridinium p-toluene sulfonate, and 2,4,4,6-tetrabromocyclohexadienone. , Benzoin tosylate, 2-nitrobenzyl tosylate, and alkyl esters of organic sulfonic acid, but may be selected from the group.
  • the underlayer film composition according to one embodiment of the present invention may further include a surfactant.
  • the content of the surfactant may be 0.01 to 1 part by weight based on 100 parts by weight of the underlayer film composition.
  • the surfactant may be an alkylbenzene sulfonate, alkylpyridinium salt, polyethylene glycols, quaternary ammonium salts, etc., but is not limited thereto.
  • the underlayer film composition according to one embodiment of the present invention may further include a crosslinking component.
  • the content of the crosslinking component may be 0.1 to 5 parts by weight based on 100 parts by weight of the underlayer film composition, and more preferably 0.1 to 3 parts by weight. When the content of the crosslinking component is included in the above range, appropriate crosslinking properties can be obtained without changing the optical properties of the underlayer film to be formed.
  • crosslinking component examples include etherified amino resins such as methylated or butylated melamine resins (specific examples being N-methoxymethyl-melamine resin or N-butoxymethyl-melamine resin) and methylation.
  • butylated urea resins specifically examples are Cymel U-65 Resin or UFR 80 Resin
  • glycoluril derivatives represented by the following formula 38 specific examples are Powderlink 1174
  • 2,6-bis (hydr Oxymethyl) -p-cresol compound 2,6-bis (hydr Oxymethyl) -p-cresol compound.
  • a bisepoxy-based compound represented by the following Chemical Formula 39 and a melamine derivative represented by the following Chemical Formula 40 may also be used as the crosslinking component.
  • Another embodiment of the present invention provides a method of forming a pattern of a device using a resist underlayer film composition, comprising: (a) providing a material layer on a substrate; (b) forming an underlayer film on the material layer using the resist underlayer film composition; (c) forming a resist layer on the underlayer film layer; (d) exposing the substrate on which the resist layer is formed; (e) developing the exposed substrate; And (f) etching the developed substrate.
  • a material layer is formed on a substrate.
  • a silicon substrate may be used, and the material constituting the material layer may be any conductive, semiconducting, magnetic or insulating material, and representative examples thereof include aluminum and silicon nitride (SiN). have. Since the method of forming the material layer is a conventional method, detailed description thereof will be omitted.
  • an underlayer film is formed using a resist underlayer film composition according to an embodiment of the present invention.
  • the underlayer film forming process may be formed by coating the resist underlayer film composition to a thickness of 500 to 4000 kPa and baking.
  • the coating process may be carried out by a spin coating process, the baking process may be carried out for 10 seconds to 10 minutes at 100 to 500 °C.
  • the coating process, the thickness of the underlayer film, the baking temperature and time is not limited to the above range, can be prepared in a variety of different forms, those skilled in the art to which the present invention belongs It will be understood that other specific forms may be practiced without changing the essential features.
  • a resist layer (photosensitive imaging layer) is formed on this underlayer film layer. Since the resist layer may be performed by a generally known process of coating and baking the photosensitive resist composition, detailed description thereof will be omitted herein.
  • a step of forming a silicon-containing resist underlayer film may be further performed, or a step of forming an antireflection layer may be further performed.
  • the resist layer is exposed.
  • This exposure process is performed using various exposure sources, for example, ArF or EUV (extreme UV), an E-beam, and the like.
  • a baking process is performed to cause a chemical reaction in the exposure area. This baking process may be carried out for about 60 to 90 seconds in the temperature range of about 90 to 120 °C.
  • a development process is performed to remove the lower layer film and the resist layer.
  • the said developing process can be performed with basic aqueous solution.
  • basic aqueous solution developer an aqueous tetramethylammonium hydroxide (TMAH) solution may be used.
  • TMAH aqueous tetramethylammonium hydroxide
  • the exposure source used is an ArF excimer laser, a line and space pattern of 80 to 100 nm may be formed at a dose of about 5 to 30 mJ / cm 2.
  • the resist pattern obtained from the process as described above is used as a mask, and is etched using a specific etching gas, for example, a halogen gas or a plasma such as a fluorocarbon gas such as CHF 3 , CF 4, or the like.
  • a specific etching gas for example, a halogen gas or a plasma such as a fluorocarbon gas such as CHF 3 , CF 4, or the like.
  • the stripper may then be used to remove the resist pattern remaining on the substrate to form the desired pattern.
  • a semiconductor integrated circuit device can be provided.
  • compositions of the present invention and formed lithographic structures can be used in the manufacture and design of integrated circuit devices in accordance with conventional semiconductor device fabrication processes.
  • it can be used to form patterned material layer structures such as metal wiring, holes for contact or bias, insulation sections (e.g., damascene or shallow trench isolation), trenches for capacitor structures, and the like.
  • patterned material layer structures such as metal wiring, holes for contact or bias, insulation sections (e.g., damascene or shallow trench isolation), trenches for capacitor structures, and the like.
  • the invention is not limited to any particular lithographic technique or device structure.
  • a nitrogen gas was introduced into a 500 m four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas inlet tube. , PGMEA) and stir well. After 15 minutes, 2.86 g (0.015 mol) of pyridinium p-toluene sulfonate was slowly added thereto, followed by reaction at 100 to 12 hours. After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator. Then diluted with methanol and adjusted to a solution of 15 wt% concentration.
  • Nitrogen gas was introduced into a 500 m four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas introduction tube, and 69.1 g (0.30 mole) of pyrenecaraldehyde and 38.2 g of benzoaldehyde were contained in 257 g of propylene glycol monomethyl ether acetate Stir well. After 15 minutes, 2.86 g (0.015 mol) of pyridinium p-toluene sulfonate was slowly added thereto, followed by reaction at 100 to 12 hours. After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator.
  • Nitrogen gas was introduced into a 500m four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas inlet tube, and 547.5 g (0.22 mol) of hydroxypyrene carboaldehyde and 41.2 g of 2-naphthalaldehyde were 227.5 g of propylene glycol. It was contained in monomethyl ether acetate and stirred well. After 15 minutes, 2.10 g (0.011 mol) of pyridinium p-toluene sulfonate was slowly added thereto, followed by reaction at 100 to 24 hours. After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator.
  • Nitrogen gas was introduced into a 500m four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas introduction tube, and 70.1 g (0.22 mol) of perylene carboaldehyde and 30.4 g of hexanal were added to 230 g of propylene glycol monomethyl ether acetate. Contain and stir well. After 15 minutes, 2.38 g (0.013 mol) of pyridinium p-toluene sulfonate was slowly added thereto, followed by reaction at 100 to 24 hours. After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator.
  • Nitrogen gas was introduced into a 500m four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas inlet tube, and 56.2 g (0.22 mol) of chlorocarboaldehyde and 31.9 g of 2-naphthalene carboaldehyde were 209 g of propylene glycol mono Put in methyl ether acetate and stir well. After 15 minutes, 1.62 g (0.0085 mol) of pyridinium p-toluene sulfonate was slowly added thereto, followed by reaction at 130 at 24 hours. After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator.
  • Nitrogen gas was introduced into a 500-meter four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas introduction tube, while 109.2 g (0.50 mol) of 1-hydroxypyrene and 18.2 g of paraformaldehyde were 308 g of propylene glycol monomethyl ether acetate. (Propyleneglycolmonomethyletheracetate, PGMEA) and stir well. After 15 minutes, 4.76 g (0.025 mol) of pyridinium p-toluene sulfonate was slowly added thereto, followed by reaction at 100 to 12 hours. After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator.
  • PGMEA Propyleneglycolmonomethyletheracetate
  • Each of the sample solutions prepared in Examples 1 to 5 was coated on a silicon wafer by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the prepared sample solution was coated on a silicon wafer by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the prepared sample solution was coated on a silicon wafer by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the refractive index n and extinction coefficient k of the formed film were obtained, respectively.
  • the instrument used was Ellipsometer (J. A. Woollam) and the measurement results are shown in Table 1.
  • the film prepared with the sample solution according to Examples 1 to 5 has a refractive index and absorbance (absorption coefficient) that can be used as an antireflection film at an ArF (193 nm) wavelength.
  • the films prepared with the sample solutions of Comparative Examples 1 and 2 were found to have a refractive index and an absorbance that can be used as antireflection films at an ArF (193 nm) wavelength, but compared to Examples 1 to 5, the relatively low refractive index was confirmed.
  • sample solutions prepared in Examples 1 to 5 and Comparative Examples 1 and 2 were respectively coated on a silicon wafer coated with aluminum by spin-coating, and baked at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the ArF photoresist was coated on each of the formed films, baked at 110 ° C. for 60 seconds, exposed to light using an ASML (XT: 1450G, NA 0.93) exposure apparatus, and developed using TMAH (2.38 wt% aqueous solution). And the line and space pattern of 60nm was examined using FE-SEM, respectively.
  • the margin of focus (EL) margin according to the change of the exposure dose and the depth of focus (DoF) margin due to the distance change with the light source were examined. The results are shown in Table 2.
  • the sample solutions prepared in Comparative Examples 1 and 2 were coated on a silicon wafer coated with aluminum by spin-coating and baked at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the ArF photoresist was coated on the formed film, baked at 110 ° C. for 60 seconds, exposed to light using an exposure equipment of ASML (XT: 1450G, NA 0.93), and developed using TMAH (2.38 wt% aqueous solution). And the line and space pattern of 60nm was examined using FE-SEM.
  • DoF margin of focus
  • EL exposure latitude
  • the films obtained with the sample solutions of Examples 1 to 5 showed good results in terms of pattern profile and margin.
  • the films prepared with the sample solutions according to Comparative Examples 1 and 2 were found to be relatively disadvantageous in the pattern profile or margin, which may be due to the difference in absorption characteristics at ArF (193 nm) wavelength.
  • the sample solutions prepared in Examples 1 to 5 and Comparative Examples 1 and 2 were respectively coated on a silicon wafer coated with aluminum by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the ArF photoresist was coated on each of the formed films, baked at 110 ° C. for 60 seconds, exposed to light using an ASML (XT: 1450G, NA 0.93) exposure apparatus, and then developed using TMAH (2.38 wt% aqueous solution), respectively. A line and space pattern was obtained.
  • the sample solutions prepared in Comparative Examples 1 and 2 were coated on a silicon wafer coated with aluminum by spin-coating and baked at 200 ° C. for 60 seconds to form a film having a thickness of 1500 ⁇ .
  • the ArF photoresist was coated on the formed film, baked at 110 ° C. for 60 seconds, exposed using ASML (XT: 1450G, NA 0.93) exposure equipment, and developed under TMAH (2.38 wt% aqueous solution) to give 60 nm line and space. (line and space) patterns were obtained.

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  • Engineering & Computer Science (AREA)
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  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)

Abstract

L'invention concerne un composé contenant un noyau aromatique pour une sous-couche de réserve, une composition de sous-couche de réserve le contenant, ainsi qu'un procédé de formation de motif de dispositif au moyen de cette composition. Le composé selon l'invention contient une unité récurrente exprimée par la formule chimique 1-1 et une unité récurrente exprimée par la formule chimique 1-2.
PCT/KR2010/008854 2010-07-06 2010-12-10 Composé contenant un noyau aromatique pour une sous-couche de réserve, composition de sous-couche de réserve le contenant et procédé de formation de motif de dispositif au moyen de cette composition WO2012005418A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2010-0064918 2010-07-06
KR20100064918A KR101400183B1 (ko) 2010-07-06 2010-07-06 레지스트 하층막용 방향족 고리 함유 화합물, 이를 포함하는 레지스트 하층막 조성물 및 이를 이용하는 소자의 패턴 형성 방법

Publications (1)

Publication Number Publication Date
WO2012005418A1 true WO2012005418A1 (fr) 2012-01-12

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PCT/KR2010/008854 WO2012005418A1 (fr) 2010-07-06 2010-12-10 Composé contenant un noyau aromatique pour une sous-couche de réserve, composition de sous-couche de réserve le contenant et procédé de formation de motif de dispositif au moyen de cette composition

Country Status (3)

Country Link
KR (1) KR101400183B1 (fr)
TW (1) TWI443121B (fr)
WO (1) WO2012005418A1 (fr)

Cited By (2)

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CN103896736A (zh) * 2012-12-27 2014-07-02 第一毛织株式会社 用于硬掩模组合物的单体和包含单体的硬掩模组合物及使用硬掩模组合物形成图案的方法
US10364221B2 (en) * 2015-07-06 2019-07-30 Samsung Sdi Co., Ltd. Monomer, organic layer composition, organic layer, and method of forming patterns

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101531610B1 (ko) 2011-12-30 2015-06-24 제일모직주식회사 하드마스크 형성용 조성물, 이를 이용한 패턴 형성 방법 및 상기 패턴을 포함하는 반도체 집적회로 디바이스
KR20180027989A (ko) * 2016-09-07 2018-03-15 동우 화인켐 주식회사 하드마스크용 조성물
KR102383692B1 (ko) * 2017-06-30 2022-04-05 동우 화인켐 주식회사 하드마스크용 조성물

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KR20060116133A (ko) * 2005-05-09 2006-11-14 제일모직주식회사 반사방지성을 갖는 하드마스크 조성물
KR100866015B1 (ko) * 2007-05-25 2008-10-30 제일모직주식회사 반사방지 하드마스크 조성물 및 이를 이용한 재료의 패턴화방법
KR20080107210A (ko) * 2007-06-05 2008-12-10 제일모직주식회사 반사방지 하드마스크 조성물 및 이를 이용한 기판상 재료의패턴화 방법
KR20090068444A (ko) * 2007-12-24 2009-06-29 제일모직주식회사 반사방지 하드마스크 조성물　및　이를 이용한재료의　패턴화 방법

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Publication number Priority date Publication date Assignee Title
KR20060116133A (ko) * 2005-05-09 2006-11-14 제일모직주식회사 반사방지성을 갖는 하드마스크 조성물
KR100866015B1 (ko) * 2007-05-25 2008-10-30 제일모직주식회사 반사방지 하드마스크 조성물 및 이를 이용한 재료의 패턴화방법
KR20080107210A (ko) * 2007-06-05 2008-12-10 제일모직주식회사 반사방지 하드마스크 조성물 및 이를 이용한 기판상 재료의패턴화 방법
KR20090068444A (ko) * 2007-12-24 2009-06-29 제일모직주식회사 반사방지 하드마스크 조성물　및　이를 이용한재료의　패턴화 방법

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103896736A (zh) * 2012-12-27 2014-07-02 第一毛织株式会社 用于硬掩模组合物的单体和包含单体的硬掩模组合物及使用硬掩模组合物形成图案的方法
US9284245B2 (en) 2012-12-27 2016-03-15 Cheil Industries, Inc. Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition
US10364221B2 (en) * 2015-07-06 2019-07-30 Samsung Sdi Co., Ltd. Monomer, organic layer composition, organic layer, and method of forming patterns

Also Published As

Publication number Publication date
TW201202295A (en) 2012-01-16
KR20120004192A (ko) 2012-01-12
TWI443121B (zh) 2014-07-01
KR101400183B1 (ko) 2014-05-30

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