US20130189533A1 - Resist underlayer film forming composition for lithography containing polyether structure-containing resin - Google Patents

Resist underlayer film forming composition for lithography containing polyether structure-containing resin Download PDF

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Publication number
US20130189533A1
US20130189533A1 US13/825,925 US201113825925A US2013189533A1 US 20130189533 A1 US20130189533 A1 US 20130189533A1 US 201113825925 A US201113825925 A US 201113825925A US 2013189533 A1 US2013189533 A1 US 2013189533A1
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Prior art keywords
underlayer film
resist underlayer
resist
forming composition
formula
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US13/825,925
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English (en)
Inventor
Hiroaki Okuyama
Yasunobu Someya
Masakazu Kato
Tetsuya Shinjo
Keisuke Hashimoto
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Nissan Chemical Corp
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Nissan Chemical Corp
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Assigned to NISSAN CHEMICAL INDUSTRIES, LTD. reassignment NISSAN CHEMICAL INDUSTRIES, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HASHIMOTO, KEISUKE, KATO, MASAKAZU, OKUYAMA, HIROAKI, SHINJO, TETSUYA, SOMEYA, YASUNOBU
Publication of US20130189533A1 publication Critical patent/US20130189533A1/en
Abandoned legal-status Critical Current

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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
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/094—Multilayer resist systems, e.g. planarising 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
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
    • G03F7/2059—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a scanning corpuscular radiation beam, e.g. an electron beam
    • 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
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • 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
    • 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
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
    • H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
    • 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
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
    • H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
    • H01L21/3083—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane
    • H01L21/3086—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane characterised by the process involved to create the mask, e.g. lift-off masks, sidewalls, or to modify the mask, e.g. pre-treatment, post-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
    • C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31942—Of aldehyde or ketone condensation product

Definitions

  • the present invention relates to a resist underlayer film forming composition for lithography that is effectively used for processing of a semiconductor substrate, a resist pattern forming method employing the resist underlayer film forming composition, and a method for producing a semiconductor device.
  • the fine processing is a processing method including: forming a thin film of a photoresist composition on a substrate to be processed such as a silicon wafer; irradiating the resultant thin film with an active ray such as an ultraviolet ray through a mask pattern in which a pattern of a semiconductor device is depicted for development; and etching the substrate to be processed such as a silicon wafer using the resultant photoresist pattern as a protecting film.
  • a resist underlayer film for such a process there have started to be required a resist underlayer film for lithography having a selection ratio of a dry etching rate close to that of the resist, a resist underlayer film for lithography having a selection ratio of a dry etching rate smaller than that of the resist, and a resist underlayer film for lithography having a selection ratio of a dry etching rate smaller than that of the semiconductor substrate, as a resist underlayer film, unlike a conventional resist underlayer film having high etching rate property (high etching rate).
  • Patent Document 1 a heat resistant resist underlayer film having a fluorene structure is disclosed.
  • Patent Document 1 International Publication No. WO 2010/041626 pamphlet
  • the present invention provides a resist underlayer film forming composition for using for a lithography process of the production of semiconductor devices. It is an object of the present invention to provide a resist underlayer film for lithography causing no intermixing with a resist layer, providing an excellent resist pattern, and having: a selection ratio of a dry etching rate close to that of the resist; a selection ratio of a dry etching rate smaller than that of the resist; or a selection ratio of a dry etching rate smaller than that of the semiconductor substrate.
  • the present invention also provides a resist underlayer film for lithography capable of imparting performance of effectively absorbing light reflected on the substrate when irradiated light having a wavelength of 248 nm, 193 nm, 157 nm, or the like is used for fine processing. Furthermore, it is an object of the present invention to provide a resist pattern forming method using the resist underlayer film forming composition. Then, the present invention provides a resist underlayer film forming composition for forming a resist underlayer film providing heat resistance in combination with other advantageous properties.
  • the present invention is, according to a first aspect, a resist underlayer film forming composition for lithography, containing a polymer containing a unit structure of Formula (1):
  • Ar 1 is a C 6-50 arylene group or an organic group containing a heterocyclic group
  • Ar 2 , Ar 3 , and Ar 4 are individually a C 6-50 arylene group or an organic group containing a heterocyclic group; and T is a carbonyl group or a sulfonyl group), or a combination of the unit structure of Formula (1) and the unit structure of Formula (2),
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (1), and the organic group of Ar 1 is an organic group containing a fluorene structure,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (2), and the organic group of Ar 2 is an organic group containing a fluorene structure,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing a combination of the unit structure of Formula (1) and the unit structure of Formula (2), and at least one of the organic group of Ar 1 and the organic group of Ar 2 is an organic group containing a fluorene structure,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (1), and the organic group of Ar 1 is an organic group containing a combination of an arylene group with a group containing a carbon-carbon triple bond and/or a group containing a carbon-carbon double bond,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (2), and the organic group of Ar 2 is an organic group containing a combination of an arylene group with a group containing a carbon-carbon triple bond and/or a group containing a carbon-carbon double bond,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing a combination of the unit structure of Formula (1) and the unit structure of Formula (2), and at least one of the organic group of Ar 1 and the organic group of Ar 2 is an organic group containing a combination of an arylene group with a group containing a carbon-carbon triple bond and/or a group containing a carbon-carbon double bond,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (1), and the organic group of Ar 1 is an organic group containing a biphenylene structure,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (2), and the organic group of Ar 2 is an organic group containing a biphenylene structure,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing a combination of the unit structure of Formula (1) and the unit structure of Formula (2), and at least one of the organic group of Ar 1 and the organic group of Ar 2 is an organic group containing a biphenylene structure,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing the unit structure of Formula (2), and at least one of the organic group of Ar 3 and the organic group of Ar 4 is a phenylene group,
  • the resist underlayer film forming composition according to the first aspect in which the resist underlayer film forming composition for lithography contains a polymer containing a combination of the unit structure of Formula (1) and the unit structure of Formula (2), and at least one of the organic group of Ar 3 and the organic group of Ar 4 is a phenylene group,
  • the resist underlayer film forming composition according to any one of the first aspect to the twelfth aspect further containing an acid or an acid generator,
  • a resist underlayer film obtained by applying the resist underlayer film forming composition described in any one of the first aspect to the thirteenth aspect onto a semiconductor substrate and baking the resultant film,
  • a method for producing a semiconductor device including: a process of forming an underlayer film with the resist underlayer film forming composition described in any one of the first aspect to the thirteenth aspect on a semiconductor substrate; a process of forming a resist film on the underlayer film; a process of irradiating the resist film with light or an electron beam and developing the resist film so as to form a resist pattern; a process of etching the underlayer film according to the resist pattern of the resist film; and a process of processing the semiconductor substrate according to the patterned underlayer film, and
  • a method for producing a semiconductor device including: a process of forming an underlayer film with the resist underlayer film forming composition described in any one of the first aspect to the thirteenth aspect on a semiconductor substrate; a process of forming a hardmask on the underlayer film; a process of further forming a resist film on the hardmask; a process of irradiating the resist film with light or an electron beam and developing the resist film so as to form a resist pattern; a process of etching the hardmask according to the resist pattern of the resist film; a process of etching the underlayer film according to the patterned hardmask; and a process of processing the semiconductor substrate according to the patterned underlayer film.
  • an advantageous pattern shape of a resist can be formed without causing intermixing with an upper layer of the resist underlayer film.
  • the resist underlayer film forming composition of the present invention can have performance of effectively suppressing reflection on the substrate and provide an effect as an anti-reflective coating for exposure light in combination with other advantageous properties.
  • the resist underlayer film forming composition of the present invention can provide an excellent resist underlayer film having a selection ratio of a dry etching rate close to that of the resist, a selection ratio of a dry etching rate smaller than that of the resist, or a selection ratio of a dry etching rate smaller than that of the semiconductor substrate.
  • thinning of the resist is performed.
  • a process including transferring a resist pattern to an underlayer film thereof by etching process and further transferring the pattern transferred to the underlayer film to an underlayer film thereof using a gas having a different gas composition is repeatedly performed so that the substrate is processed.
  • the resist underlayer film and the forming composition thereof of the present invention are effective for these processes and when the substrate is processed using the resist underlayer film of the present invention, the resist underlayer film has satisfactory etching resistance relative to the substrate to be processed (for example, a thermally oxidized silicon film, a nitride silicon film, a polysilicon film, and the like on the substrate).
  • the resist underlayer film of the present invention can be used as a planarization film, a resist underlayer film, a contamination preventing film for the resist layer, and a film having dry etching selectivity.
  • Use of the resist underlayer film of the present invention makes it possible to easily and accurately perform the formation of a resist pattern in a lithography process of the semiconductor production.
  • a process including: forming a resist underlayer film with a resist underlayer film forming composition on a substrate; forming a hardmask on the resist underlayer film; forming a resist film on the hardmask; forming a resist pattern by exposure and development; transferring the resist pattern to the hardmask; transferring the resist pattern transferred to the hardmask to the resist underlayer film; and processing the semiconductor substrate according to the resist underlayer film.
  • the formation of the hardmask is performed by a coating-type composition containing an organic polymer or an inorganic polymer and a solvent, and a case where the formation of the hardmask is performed by vacuum deposition of an inorganic substance.
  • the used polymer is a copolymer containing a polyether structure, for example, a unit structure of fluorene naphthol and a unit structure of arylene alkylene, so that the used polymer has extremely high heat resistance and is difficult to cause thermal degradation even by the deposition of the deposited substance.
  • the present invention is a resist underlayer film forming composition for lithography containing a polymer containing a unit structure of Formula (1), a unit structure of Formula (2), or a unit structure containing a combination of these unit structures.
  • the resist underlayer film forming composition may contain a crosslinking agent, an acid, and if necessary, an additive such as an acid generator and a surfactant.
  • the solid content of the composition is 0.1 to 70% by mass or 0.1 to 60% by mass.
  • the solid content is a content of a component remaining after a solvent is removed from the resist underlayer film forming composition.
  • the above polymer can be contained in a content of 1 to 100% by mass, 1 to 99% by mass, or 50 to 99% by mass.
  • the polymer used in the present invention has a weight average molecular weight of 600 to 1,000,000, preferably 1,000 to 200,000.
  • the unit structure of Formula (1) is a unit structure having a polyether structure and the unit structure of Formula (2) is a unit structure having a polyetheretherketone structure or a polyetherethersulfon structure.
  • Ar 1 is a C 6-50 arylene group or an organic group containing a heterocyclic group.
  • the organic group is, for example, a divalent to tetravalent group.
  • Ar 2 , Ar 3 , and Ar 4 are individually a C 6-50 arylene group or an organic group containing a heterocyclic group, and T is a carbonyl group or a sulfonyl group.
  • Arylene groups or heterocyclic groups in the organic groups of Ar 1 to Ar 4 can be used individually or in combination of two or more of them.
  • the arylene group and the heterocyclic group are, for example, a divalent to tetravalent group.
  • the C 6-50 arylene group is a divalent organic group corresponding to an aryl group and examples thereof include divalent groups corresponding to a phenyl group, an o-methylphenyl group, a m-methylphenyl group, a p-methylphenyl group, an o-chlorophenyl group, a m-chlorophenyl group, a p-chlorophenyl group, an o-fluorophenyl group, a p-fluorophenyl group, an o-methoxyphenyl group, a p-methoxyphenyl group, a p-nitrophenyl group, a p-cyanophenyl group, an ⁇ -naphthyl group, a ⁇ -naphthyl group, an o-biphenylyl group, a m-biphenylyl group, a p-biphenylyl group, a 1-anth
  • heterocyclic group examples include organic groups corresponding to heterocyclic rings such as pyrrole, thiophene, furan, imidazole, triazole, oxazole, thiazole, pyrazole, isoxazole, isothiazole, pyridine, pyridazine, pyrimidine, pyrazine, piperidine, piperazine, morpholine, pyran, and carbazole.
  • the organic group containing a C 6-50 arylene group can be used as the above arylene group alone or as a combination of the above arylene group with a group containing a carbon-carbon triple bond and/or a group containing a carbon-carbon double bond.
  • Examples of the organic group containing the above arylene group include an organic group containing a fluorene structure or an organic group containing a biphenylene structure.
  • the unit structure of the polymer used in the present invention can be exemplified as follows.
  • the resist underlayer film forming composition of the present invention may contain a crosslinking agent component.
  • the crosslinking agent include a melamine-based crosslinking agent, a substituted urea-based crosslinking agent, and a polymer thereof-based crosslinking agent.
  • the crosslinking agent is preferably a crosslinking agent having at least two crosslinkage forming substituents and examples thereof include compounds such as methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, and methoxymethylated thiourea.
  • a condensation product of these compounds can also be used.
  • crosslinking agent a crosslinking agent having high heat resistance
  • a compound containing, in the molecule thereof, a crosslinkage forming substituent having an aromatic ring such as a benzene ring and a naphthalene ring
  • an aromatic ring such as a benzene ring and a naphthalene ring
  • Examples of such a compound include a compound having a partial structure of Formula (4) below, a polymer or an oligomer having a repeating unit of Formula (5) below.
  • R 7 and R 8 are individually a hydrogen atom, a C 1-10 alkyl group, or a C 6-20 aryl group; and n7 is an integer of 1 to 4, n8 is an integer of 1 to (5 ⁇ n7) and n7+n8 is an integer of 2 to 5.
  • R 9 is a hydrogen atom or a C 1-10 alkyl group; R 10 is a C 1-10 alkyl group; and n9 is an integer of 1 to 4, n10 is an integer of 0 to (4 ⁇ n9) and n9+n10 is an integer of 1 to 4.
  • the polymer and the oligomer can be used in a range of the number of repeating unit structures of 2 to 100 or 2 to 50. Examples of the alkyl group and the aryl group include individually the above examples.
  • the compound of Formula (4), the polymer, oligomer thereof and the compound of Formula (5), the polymer and oligomer thereof are exemplified as follows.
  • TM-BIP-A TM-BIP-A
  • the additive amount of the crosslinking agent is varied depending on the used coating solvent, the used ground substrate, the required viscosity of solution, the required film shape, and the like, it is 0.001 to 80% by mass, preferably 0.01 to 50% by mass, further preferably 0.05 to 40% by mass, based on the total mass of the solid content.
  • the crosslinking agent may effect a crosslinking reaction by self-condensation, when a crosslinkable substituent exists in the above polymer of the present invention, the crosslinking agent can effect the crosslinking reaction with such a crosslinkable substituent.
  • an acidic compound such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, and naphthalenecarboxylic acid or/and a thermoacid generator such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and organic sulfonic acid alkyl esters can be blended.
  • the blending amount thereof is 0.0001 to 20% by mass, preferably 0.0005 to 10% by mass, more preferably 0.01 to 3% by mass, based on the total mass of the solid content.
  • a photoacid generator for conforming the acidity of the underlayer film forming composition to the acidity of the photoresist applied as an upper layer of the underlayer film thereon in a lithography process, a photoacid generator can be blended.
  • the photoacid generator include: onium salt photoacid generators such as bis(4-tert-butylphenyl)iodonium trifluoromethanesulfonate and triphenylsulfonium trifluoromethanesulfonate; halogen-containing compound photoacid generators such as phenyl-bis(trichloromethyl)-s-triazine; and sulfonic acid-based photoacid generators such as benzoin tosylate and N-hydroxysuccinimide trifluoromethanesulfonate.
  • the content of the photoacid generator is 0.2 to 10% by mass, preferably 0.4 to 5% by mass, based on the total mass of the solid content.
  • an additional light absorber besides the above components, if necessary, an additional light absorber, a rheology controlling agent, an adhesion assistant, a surfactant, and the like can be added.
  • the additional light absorber there can be preferably used, for example, commercially available light absorbers described in “Technology and market of industrial dyestuff” (published by CMC Publishing CO., Ltd.) or “Dye handbook” (published by the Society of Synthetic Organic Chemistry, Japan) such as C. I. Disperse Yellow 1, 3, 4, 5, 7, 8, 13, 23, 31, 49, 50, 51, 54, 60, 64, 66, 68, 79, 82, 88, 90, 93, 102, 114, and 124; C. I. Disperse Orange 1, 5, 13, 25, 29, 30, 31, 44, 57, 72, and 73; C. I.
  • the light absorber is blended usually in a content of 10% by mass or less, preferably 5% by mass or less, based on the total mass of the solid content of the resist underlayer film material for lithography.
  • the rheology controlling agent is added for the purpose of mainly enhancing the fluidity of the resist underlayer film forming composition, particularly enhancing the homogeneity of the film thickness of the resist underlayer film or enhancing the filling property of the resist underlayer film forming composition into the inside of a hole, in a baking process.
  • the rheology controlling agent include: phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butylisodecyl phthalate; adipic acid derivatives such as di-n-butyl adipate, diisobutyl adipate, diisooctyl adipate, and octyldecyl adipate; maleic acid derivatives such as di-n-butyl maleate, diethyl maleate, and dinonyl maleate; oleic acid derivatives such as methyl oleate, butyl oleate, and tetrahydrofurfuryl oleate; and stearic acid derivatives such as n-butyl stearate and glyceryl stearate. These rheology controlling agents are blended in a content of usually less than 30% by mass, based on
  • the adhesion assistant is added for the purpose of mainly enhancing the adhesion of the resist underlayer film forming composition and the substrate or the resist, particularly preventing the resist from being peeled during development.
  • Specific examples of the adhesion assistant include: chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, and chloromethyldimethylchlorosilane; alkoxysilanes such as trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, and phenyltriethoxysilane; silazanes such as hexamethyldisilazane, N,N′-bis(trimethlsilyl)urea, dimethyltrimethylsilylamine, and trimethylsilylimidazol; silanes such as vinyltrichlor
  • a surfactant for causing no pinhole and no striation and further, enhancing the applicability relative to a surface unevenness, a surfactant can be blended.
  • the surfactant include: nonionic surfactants, for example polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether, polyoxyethylene alkylallyl ethers such as polyoxyethylene octylphenol ether and polyoxyethylene nonylphenol ether, polyoxyethylene-polyoxypropylene block copolymers, sorbitan fatty acid esters such as sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate, polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene
  • the blending amount of the surfactant is usually 2.0% by mass or less, preferably 1.0% by mass or less, based on the total mass of the solid content of the resist underlayer film material for lithography of the present invention.
  • These surfactants may be used individually or in combination of two or more of them.
  • examples of the solvent for dissolving the polymer, the crosslinking agent component, the crosslinking catalyst, and the like include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methylcellosolve acetate, ethylcellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate,
  • a high boiling point-solvent such as propylene glycol monobutyl ether and propylene glycol monobutyl ether acetate can be mixed to be used.
  • a high boiling point-solvent such as propylene glycol monobutyl ether and propylene glycol monobutyl ether acetate
  • propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, and cyclohexanone are preferred for enhancing the leveling property.
  • a photoresist As the resist used in the present invention, a photoresist, an electron beam resist, and the like can be used.
  • both of a negative-type photoresist and a positive-type photoresist can be used.
  • the photoresist include: a positive-type photoresist containing a novolac resin and 1,2-naphthoquinonediazide sulfonic acid ester; a chemical amplification type photoresist containing a binder having a group elevating alkali dissolving rate by being decomposed by an acid, and a photoacid generator; a chemical amplification type photoresist containing an alkali-soluble binder, a low molecule compound elevating alkali dissolving rate of a photoresist by being decomposed by an acid, and a photoacid generator; a chemical amplification type photoresist containing a binder having a group elevating alkali dissolving rate by being decomposed by an acid, a low molecule compound elevating alkal
  • Examples of the electron beam resist applied and formed on the resist underlayer film for lithography in the present invention include: a composition containing a resin containing a Si—Si bond in the backbone thereof and containing an aromatic ring at a terminal thereof, and an acid generator generating an acid by being irradiated with an electron beam; or a composition containing poly(p-hydroxystyrene) in which a hydroxy group is substituted with an organic group containing N-carboxyamine and an acid generator generating an acid by being irradiated with an electron beam.
  • an acid generated from the acid generator by electron beam irradiation is reacted with an N-carboxyaminoxy group in a side chain of the polymer and the side chain of the polymer is decomposed to a hydroxy group to exhibit alkali solubility and to be dissolved in an alkaline developer, so that a resist pattern is formed.
  • Examples of the acid generator generating an acid by the electron beam irradiation include: a halogenated organic compound such as 1,1-bis[p-chlorophenyl]-2,2,2-trichloroethane, 1,1-bis[p-methoxyphenyl]-2,2,2-trichloroethane, 1,1-bis[p-chlorophenyl]-2,2-dichloroethane, and 2-chloro-6-(trichloromethyl)pyridine; an onium salt such as a triphenylsulfonium salt and a diphenyliodonium salt; and a sulfonic acid ester such as nitrobenzyl tosylate and dinitrobenzyl tosylate.
  • a halogenated organic compound such as 1,1-bis[p-chlorophenyl]-2,2,2-trichloroethane, 1,1-bis[p-methoxyphenyl]-2,2,2-trichloroethane, 1,1
  • Examples of the developer for the resist having the resist underlayer film formed using the resist underlayer film material for lithography of the present invention include aqueous solutions of alkalis such as: inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and ammonia water; primary amines such as ethylamine and n-propylamine; secondary amines such as diethylamine and di-n-butylamine; tertiary amines such as triethylamine and methyldiethylamine; alcoholamines such as dimethylethanolamine and triethanolamine; quaternary ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, and choline; and cyclic amines such as pyrrole and piperidine.
  • alkalis such as: inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium si
  • an appropriate amount of alcohols such as isopropyl alcohol or a nonion-based or the like surfactant may be added to be used.
  • a preferred developer is a quaternary ammonium salt and further preferred developers are tetramethylammonium hydroxide and choline.
  • a resist underlayer film forming composition is applied by an appropriate coating method such as spinner and coater, and is baked to be cured to produce a coating-type underlayer film.
  • the resist underlayer film has a film thickness of preferably 0.01 to 3.0 ⁇ m.
  • the conditions for baking after coating are at 80 to 350° C. and for 0.5 to 120 minutes.
  • the resist is applied and the resist is irradiated with light or an electron beam through a predetermined mask. Then, by developing, rinsing, and drying the resist, an advantageous resist pattern can be obtained. If necessary, heating after irradiation with light or an electron beam (PEB: Post Exposure Bake) can be performed. Then, by removing the resist underlayer film in a part at which the resist is removed by development in the above process by dry etching, a desired pattern can be formed on the substrate.
  • PEB Post Exposure Bake
  • the exposure light for the photoresist is a chemical ray such as a near ultraviolet ray, a far ultraviolet ray, or an extreme ultraviolet ray (for example, EUV) and as the exposure light, light of a wavelength of 248 nm (KrF laser light), 193 nm (ArF laser light), or 157 nm (F 2 laser light) is used.
  • the light irradiating method is not particularly limited to be used as long as the method is a method capable of generating an acid from the photoacid generator and the light irradiating method is performed with an exposure dose of 1 to 2,000 mJ/cm 2 , 10 to 1,500 mJ/cm 2 , or 50 to 1,000 mJ/cm 2 .
  • the electron beam irradiation for the electron beam resist can be performed, for example, using an electron beam irradiating apparatus.
  • a semiconductor device can be produced through a process of forming a resist underlayer film with a resist underlayer film forming composition on a semiconductor substrate, a process of forming a resist film on the resist underlayer film, a process of forming a resist pattern by light irradiation or electron beam irradiation and development, a process of etching the resist underlayer film according to the resist pattern, and a process of processing the semiconductor substrate according to the patterned resist underlayer film.
  • a resist underlayer film for such a process there has started to be required a resist underlayer film for lithography having a selection ratio of a dry etching rate close to that of the resist, a resist underlayer film for lithography having a selection ratio of a dry etching rate smaller than that of the resist, and a resist underlayer film for lithography having a selection ratio of a dry etching rate smaller than that of the semiconductor substrate, as a resist underlayer film, unlike a conventional resist underlayer film having high etching rate property.
  • reflection preventing ability can also be imparted, so that such a resist underlayer film can provide a function of a conventional anti-reflective coating in combination with other advantageous properties.
  • a process of making the resist pattern and the resist underlayer film thinner than the pattern width during development of the resist, during dry etching of the resist underlayer film As a resist underlayer film for such a process, there has started to be required a resist underlayer film having a selection ratio of a dry etching rate close to that of the resist, unlike a conventional high etching rate anti-reflective coating. To such a resist underlayer film, a reflection preventing ability can be imparted, so that such a resist underlayer film can provide a function of a conventional anti-reflective coating in combination with other advantageous properties.
  • the resist underlayer film of the present invention is formed on a substrate, and then on the resist underlayer film, either directly or if necessary, through a film formed with one layer or several layers of coating material on the resist underlayer film, the resist can be applied. This makes it possible to process the substrate by selecting an appropriate etching gas even when the pattern width of the resist is small and the resist is coated in a small thickness for preventing a pattern collapse.
  • a semiconductor device can be produced.
  • the resist underlayer film forming composition for lithography of the present invention when the effect thereof as an anti-reflective coating is considered, a light absorbing moiety is incorporated into the skeleton, so that there is no substance diffused into the photoresist during heating and drying of the composition. Furthermore the light absorbing moiety has satisfactorily high light absorbing performance; therefore, the composition has high effect of preventing reflected light.
  • the resist underlayer film forming composition for lithography of the present invention has high thermal stability, can prevent contamination of an upper layer film of the resist underlayer film by a decomposed substance during baking the resist underlayer film, and can allow leeway in the temperature margin for the baking process.
  • the resist underlayer film material for lithography of the present invention can be used, depending on the process condition, as a film having a function of preventing reflection of light and further, a function of preventing an interaction between the substrate and the photoresist or a function of preventing an adverse action of a material used for the photoresist or a substance generated during light exposure of the photoresist against the substrate.
  • reaction filtrate was mixed with about 10 mL of a mixture of N-methyl-2-pyrrolidinone and 2 mol/L hydrochloric acid in a volume ratio of 90:10. Then, the resultant reaction filtrate was charged into methanol to perform reprecipitation purification of the reaction filtrate.
  • the resultant precipitate was washed with water and methanol and was vacuum-dried at 85° C. for about one day to obtain a polyether used in the present invention.
  • the obtained polymer corresponded to Formula (3-1).
  • the obtained polymer having an ether structure was subjected to GPC analysis and the polymer had a weight average molecular weight of 6,900 and a polydispersity Mw/Mn of 1.83 in terms of standard polystyrene.
  • the obtained polymer corresponded to Formula (3-3).
  • the obtained polymer had a weight average molecular weight Mw of 51,000 and a polydispersity Mw/Mn of 5.47 that were measured in terms of polystyrene.
  • the resultant precipitate was filtered under reduced pressure and the filtered substance was dried under reduced pressure at 85° C. over one night. Then, 3.70 g of a polyether was obtained as a skin color powder.
  • the obtained polymer corresponded to Formula (3-4).
  • the obtained polymer had a weight average molecular weight Mw of 20,000 and a polydispersity Mw/Mn of 4.49 that were measured in terms of polystyrene.
  • the obtained polymer corresponded to Formula (3-5).
  • the obtained polymer had a weight average molecular weight Mw of 1,000 and a polydispersity Mw/Mn of 1.21 that were measured in terms of polystyrene.
  • the synthesized polymer was cooled down to room temperature and the reaction mixture was filtered for removing a precipitate to recover the resultant reaction filtrate.
  • the resultant precipitate was washed with water and methanol and was vacuum-dried at 85° C. for about one day to obtain a polyether used in the present invention.
  • the obtained polymer corresponded to Formula (3-6).
  • the obtained polymer having an ether structure was subjected to GPC analysis and the polymer had a weight average molecular weight of 7,600 and a polydispersity Mw/Mn of 1.96 in terms of standard polystyrene.
  • the synthesized polymer was cooled down to room temperature and the reaction mixture was filtered for removing a precipitate to recover the resultant reaction filtrate.
  • the reaction filtrate was mixed with about 10 mL of a mixture of N-methyl-2-pyrrolidinone and 2 mol/L hydrochloric acid in a volume ratio of 90:10. Then, the resultant reaction filtrate was charged into a methanol solution to perform reprecipitation purification of the reaction filtrate.
  • the resultant precipitate was washed with water and methanol and was vacuum-dried at 85° C. for about one day to obtain 19.72 g of a polyether used in the present invention.
  • the obtained polymer corresponded to Formula (3-7).
  • the obtained polymer having an ether structure was subjected to GPC analysis and the polymer had a weight average molecular weight of 15,000 and a polydispersity Mw/Mn of 2.65 in terms of standard polystyrene.
  • the synthesized polymer was cooled down to room temperature and the reaction mixture was filtered for removing a precipitate to recover the resultant reaction filtrate.
  • the reaction filtrate was mixed with about 10 mL of a mixture of N-methyl-2-pyrrolidinone and 2 mol/L hydrochloric acid in a volume ratio of 90:10. Then, the resultant reaction filtrate was charged into a methanol solution to perform reprecipitation purification of the reaction filtrate.
  • the resultant precipitate was washed with water and methanol and was vacuum-dried at 85° C. for about one day to obtain 28.39 g of a polyether used in the present invention.
  • the obtained polymer corresponded to Formula (3-8).
  • the obtained polymer having an ether structure was subjected to GPC analysis and the polymer had a weight average molecular weight of 4,400 and a polydispersity Mw/Mn of 1.70 in terms of standard polystyrene.
  • the resist underlayer film solutions prepared in Examples 1 to 10 and Comparative Examples 1 and 2 were individually applied onto a silicon wafer with a spin coater. The solution was baked on a hot plate at 240° C. for 1 minute (in Comparative Example 1: at 205° C. for 1 minute, in Comparative Example 2: at 160° C. for 1 minute) or at 400° C. for 2 minutes to form a resist underlayer film (film thickness: 0.05 ⁇ m).
  • the refractive index (n value) at a wavelength of 193 nm and optical absorptivity (k value, also called attenuation coefficient) of these resist underlayer films were measured using a spectroscopic ellipsometer. The results of the measurements are listed in Table 1.
  • Example 1 Film baked at 240° C. 1.48 0.77 Film baked at 400° C. 1.48 0.75
  • Example 2 Film baked at 240° C. 1.39 0.49 Film baked at 400° C. 1.39 0.51
  • Example 3 Film baked at 240° C. 1.55 0.59 Film baked at 400° C. 1.54 0.63
  • Example 4 Film baked at 240° C. 1.49 0.64 Film baked at 400° C. 1.63 0.73
  • Example 5 Film baked at 240° C. 1.47 0.77 Film baked at 400° C. 1.46 0.73
  • Example 6 Film baked at 240° C. 1.58 0.81 Film baked at 400° C.
  • Example 7 Film baked at 240° C. 1.49 0.72 Film baked at 400° C. 1.47 0.73
  • Example 8 Film baked at 240° C. 1.43 0.49 Film baked at 400° C. 1.40 0.51
  • Example 9 Film baked at 240° C. 1.43 0.71 Film baked at 400° C. 1.41 0.70
  • Example 10 Film baked at 240° C. 1.47 0.75 Film baked at 400° C. 1.46 0.74 Comparative Film baked at 205° C. 1.53 0.42
  • Example 2 Film baked at 400° C. Unmeasurable Unmeasurable
  • the solutions of the resist underlayer film forming composition prepared in Examples 1 to 10 were individually applied onto a silicon wafer with a spin coater.
  • the solution was baked on a hot plate at 240° C. for 1 minute (in Comparative Example 1: at 205° C. for 1 minute, in Comparative Example 2: at 160° C. for 1 minute) or at 400° C. for 2 minutes to form a resist underlayer film (film thickness: 0.20 ⁇ m).
  • the resist underlayer film was subjected to an immersion test in a solvent used for the resist such as ethyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and cyclohexanone.
  • the etcher and the etching gas used for the measurement of dry etching rates were as follows.
  • the solutions of the resist underlayer film forming composition prepared in Examples 1 to 10 and Comparative Examples 1 and 2 were individually applied onto a silicon wafer with a spin coater.
  • the solution was baked on a hot plate at 240° C. for 1 minute (in Comparative Example 1: at 205° C. for 1 minute, in Comparative Example 2: at 160° C. for 1 minute) or at 400° C. for 2 minutes to form a resist underlayer film (film thickness: 0.20 ⁇ m).
  • CF 4 gas as an etching gas
  • the dry etching rate ratio is a dry etching rate ratio (1) of (resist underlayer film baked at 240° C.)/(phenol novolac resin baked at 240° C.) and a dry etching rate ratio (2) of (resist underlayer film baked at 400° C.)/(phenol novolac resin baked at 240° C.).
  • the dry etching rate ratio is a dry etching rate ratio (1) of (resist underlayer film baked at 205° C.)/(phenol novolac resin baked at 240° C.) and a dry etching rate ratio (2) of (resist underlayer film baked at 400° C.)/(phenol novolac resin baked at 240° C.).
  • the dry etching rate ratio is a dry etching rate ratio (1) of (resist underlayer film baked at 160° C.)/(phenol novolac resin baked at 240° C.) and a dry etching rate ratio (2) of (resist underlayer film baked at 400° C.)/(phenol novolac resin baked at 240° C.).
  • the solutions of the resist underlayer film forming composition prepared in Examples 1 to 10 and Comparative Examples 1 and 2 were individually applied onto a silicon wafer with a spin coater. The solution was baked on a hot plate at 400° C. for 2 minutes to form a resist underlayer film (film thickness: 0.20 ⁇ m). The obtained film was heated with a rate of 10° C./min and was subjected to thermogravimetric analysis in the atmosphere to measure a temperature at which the mass of the film decreased by 5%. The results thereof are listed in Table 3.
  • Example 1 496° C.
  • Example 2 500° C.
  • Example 3 452° C.
  • Example 4 369° C.
  • Example 5 395° C.
  • Example 6 481° C.
  • Example 7 482° C.
  • Example 8 472° C.
  • Example 9 500° C. or more
  • Comparative Unmeasurable when baked at 400° C., the Example 1 film was sublimated
  • Comparative Unmeasurable when baked at 400° C., the Example 2 film was sublimated
  • the resist underlayer film material of the present invention used for a lithography process by a multilayer film can provide a resist underlayer film having a selection ratio of a dry etching rate close to or smaller than that of a photoresist and a selection ratio of a dry etching rate smaller than that of a semiconductor substrate and further, can provide an effect as an anti-reflective coating in combination with other advantageous properties unlike a conventional anti-reflective coating having high etching rate property.
  • the underlayer film material of the present invention has such heat resistance that allows a hardmask to be formed on the underlayer film as an upper layer of the underlayer film by vapor deposition.

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US9601325B2 (en) 2014-06-24 2017-03-21 Rohm And Haas Electronic Materials Llc Aromatic resins for underlayers
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