WO2016021594A1 - 芳香族メチロール化合物が反応したノボラック樹脂を含むレジスト下層膜形成組成物 - Google Patents
芳香族メチロール化合物が反応したノボラック樹脂を含むレジスト下層膜形成組成物 Download PDFInfo
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- WO2016021594A1 WO2016021594A1 PCT/JP2015/072081 JP2015072081W WO2016021594A1 WO 2016021594 A1 WO2016021594 A1 WO 2016021594A1 JP 2015072081 W JP2015072081 W JP 2015072081W WO 2016021594 A1 WO2016021594 A1 WO 2016021594A1
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- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- TVJIJCPNBAPRRJ-UHFFFAOYSA-N trichlorosilylmethanol Chemical compound OC[Si](Cl)(Cl)Cl TVJIJCPNBAPRRJ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
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- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
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- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- 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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09D161/04, C09D161/18 and C09D161/20
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- G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
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- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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- 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
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- 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
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
- G03F7/2006—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light using coherent light; using polarised light
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- 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
- G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
-
- G—PHYSICS
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- 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
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- 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
- G03F7/322—Aqueous alkaline compositions
-
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- 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
- G03F7/325—Non-aqueous compositions
-
- G—PHYSICS
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- 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
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
-
- 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
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—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
-
- 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
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31105—Etching inorganic layers
- H01L21/31111—Etching inorganic layers by chemical means
- H01L21/31116—Etching inorganic layers by chemical means by dry-etching
-
- 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
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31144—Etching the insulating layers by chemical or physical means using masks
Definitions
- the present invention relates to a resist underlayer film forming composition for lithography effective at the time of processing a semiconductor substrate, a method for forming a resist pattern using the resist underlayer film forming composition, and a method for manufacturing a semiconductor device.
- a thin film of a photoresist composition is formed on a substrate to be processed such as a silicon wafer, and irradiated with actinic rays such as ultraviolet rays through a mask pattern on which a semiconductor device pattern is drawn, and developed.
- actinic rays such as ultraviolet rays
- This is a processing method for etching a substrate to be processed such as a silicon wafer using the obtained photoresist pattern as a protective film.
- EUV lithography and EB lithography generally do not require a specific anti-reflection film because they do not cause diffuse reflection or standing wave from the substrate, but an auxiliary film for the purpose of improving the resolution and adhesion of the resist pattern As such, the resist underlayer film has begun to be widely studied.
- the resist pattern becomes finer, it is indispensable to make the resist thinner. This is because the resolution is reduced due to miniaturization and the formed resist pattern is likely to collapse. Therefore, it becomes difficult to maintain the resist pattern film thickness necessary for substrate processing, and not only the resist pattern but also the resist underlayer film formed between the resist and the semiconductor substrate to be processed is used as a mask during substrate processing. It became necessary to have a function.
- a lithography process is used in which at least two resist underlayer films are formed and the resist underlayer film is used as an etching mask.
- the resist pattern is transferred to the lower layer film by an etching process
- the substrate processing is performed using the lower layer film as a mask
- the resist pattern is transferred to the lower layer film by an etching process, and further transferred to the lower layer film.
- a process of repeating the process of transferring the formed pattern to the lower layer film using a different etching gas and finally processing the substrate is used.
- a resist underlayer film for a lithography process is required to have high etching resistance against an etching gas (for example, fluorocarbon) in a dry etching process.
- Examples of the polymer for the resist underlayer film include the following.
- a resist underlayer film forming composition using polymethylol carbazole is disclosed (see Patent Document 1, Patent Document 2, and Patent Document 3).
- a resist underlayer film forming composition using a fluorenephenol novolac resin is disclosed (see Patent Document 4).
- a resist underlayer film forming composition using a fluorene naphthol novolak resin is disclosed (see Patent Document 5).
- a resist underlayer film forming composition containing a resin having fluorenephenol and arylalkylene as repeating units is disclosed (see Patent Document 6 and Patent Document 7).
- a resist underlayer film forming composition using carbazole novolak is disclosed (see Patent Document 8).
- a resist underlayer film forming composition using a polynuclear phenol novolak is disclosed (see Patent Document 9).
- JP-A-2-293850 Japanese Patent Laid-Open No. 1-154050 JP-A-2-22657 JP 2005-128509 A JP 2007-199653 A JP 2007-178974 A US Pat. No. 7,378,217 International publication pamphlet WO2010 / 147155 JP 2006-259249 A
- the resist underlayer film forming composition is preferably applied and formed on a silicon wafer using a spin coater in the same manner as the resist composition from the viewpoint of productivity and economy.
- a polymer resin, a crosslinking agent, a crosslinking catalyst, etc. which are the main components of the resist underlayer film forming composition, are used in an appropriate solvent. It needs to be dissolved.
- solvents include propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, and the like used in the resist forming composition, and the resist underlayer film forming composition includes these. It must have good solubility in the solvent.
- the present invention has been made on the basis of solving such problems, and has high solubility in a resist solvent (solvent used in lithography) for exhibiting good coating film-forming properties and small dryness compared to a resist.
- An object of the present invention is to provide a resist underlayer film forming composition for lithography having an etching rate selection ratio.
- Another object of the present invention is to provide a resist pattern forming method using the resist underlayer film forming composition and a semiconductor device manufacturing method.
- a resist underlayer film formation comprising a novolac resin containing a structure (C) obtained by a reaction between an aromatic ring of an aromatic compound (A) and a hydroxy group-containing aromatic methylol compound (B) Composition
- the resist underlayer film forming composition according to the first aspect wherein the aromatic compound (A) is a component for constituting the structure (C) contained in the novolac resin
- the hydroxy group-containing aromatic methylol compound (B) is represented by the formula (1):
- Ar 1 represents an aryl group having 6 to 40 carbon atoms
- R 1 represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 2 to 2 carbon atoms.
- Y represents an oxygen atom, sulfur atom, carbonyl group, or ester group
- Z represents an alkyl group having 1 to 10 carbon atoms
- R 2 represents a hydrogen atom or a methyl group
- R 3 , R 4 Each represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cyano group, or an alkylamino group
- m is an integer of 0 to (4 + 2n).
- n represents the resist underlayer film forming composition according to the first aspect or the second aspect is a compound represented by.) Showing a degree of condensation of a benzene ring having an aryl group Ar 1,
- the hydroxy group-containing aromatic methylol compound (B) is 2-hydroxybenzyl alcohol, 4-hydroxybenzyl alcohol, or 2,6-di-tert-butyl-4-hydroxymethylphenol.
- the structure (C) has the formula (2): (In the formula (2), Ar 1 , R 1 , R 3 , R 4 and m are the same as those in the formula (1), and A 1 is the aromatic ring of the aromatic compound (A) or the aromatic ring of the novolak resin.
- the resist underlayer film forming composition according to any one of the first to fourth aspects having a structure represented by:
- the aromatic compound (A) is an aromatic amine or a phenolic hydroxy group-containing compound
- the novolak resin according to any one of the first to sixth aspects is a resin formed by a reaction between an aromatic amine or a phenolic hydroxy group-containing compound and an aldehyde or a ketone.
- the resist underlayer film forming composition As an eighth aspect, the resist underlayer film forming composition according to the seventh aspect, wherein the aromatic amine is phenylindole or phenylnaphthylamine,
- the phenolic hydroxy group-containing compound is phenol, dihydroxybenzene, trihydroxybenzene, hydroxynaphthalene, dihydroxynaphthalene, trihydroxynaphthalene, tris (4-hydroxyphenyl) methane, tris (4-hydroxyphenyl) ethane,
- the resist underlayer film forming composition according to the seventh aspect which is 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane
- the resist underlayer film forming composition according to any one of the seventh aspect to the ninth aspect in which the aldehyde is naphthaldehyde or pyrenecarboxaldehyde,
- the resist underlayer film forming composition of the present invention is effective for a lithography process in which at least two resist underlayer films for the purpose of reducing the resist film thickness are formed and the resist underlayer film is used as an etching mask.
- a processed substrate for example, a thermal silicon oxide film on the substrate, silicon nitride) Film, polysilicon film, etc.
- the resist underlayer film forming composition of the present invention is a coating composition having high solubility in a resist solvent and excellent spin coatability.
- the resist underlayer film obtained from the resist underlayer film forming composition of this invention does not redissolve in these resist solvents after coating and baking.
- the present invention is a resist underlayer film forming composition containing a novolak resin containing a structure (C) obtained by a reaction between an aromatic ring of an aromatic compound (A) and a hydroxy group-containing aromatic methylol compound (B).
- the resist underlayer film forming composition for lithography contains the resin and the solvent. And a crosslinking agent, an acid, an acid generator, surfactant, etc. can be included as needed.
- the solid content of this composition is 0.1 to 70% by mass, or 0.1 to 60% by mass.
- the solid content is the content ratio of all components excluding the solvent from the resist underlayer film forming composition. 1 to 100% by mass, or 1 to 99.9% by mass, or 50 to 99.9% by mass, or 50 to 95% by mass, or 50 to 90% by mass in the solid content Can do.
- the polymer (resin) used in the present invention has a weight average molecular weight of 600 to 1000000 or 600 to 200000.
- the hydroxy group-containing aromatic methylol compound (B) can be exemplified by a compound containing a methylol group having the structure of the formula (1) or a methoxymethyl group.
- Ar 1 represents an aryl group having 6 to 40 carbon atoms
- R 1 represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 2 to 10 carbon atoms.
- Y represents an oxygen atom, a sulfur atom, a carbonyl group, or an ester group
- Z represents an alkyl group having 1 to 10 carbon atoms.
- R 2 represents a hydrogen atom or a methyl group.
- R 3 and R 4 each represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cyano group, or an alkylamino group.
- m is an integer of 0 to (4 + 2n)
- n represents the degree of condensation of the benzene ring of the aryl group Ar 1 .
- the alkyl group is an alkyl group having 1 to 10 carbon atoms.
- the aryl group is an aryl group having 6 to 40 carbon atoms, such as a phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl.
- alkenyl group examples include alkenyl groups having 2 to 10 carbon atoms such as ethenyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-ethenyl group, 1-butenyl group, and 2-butenyl group.
- alkynyl group examples include ethynyl group and propargyl group.
- Y represents an oxygen atom, a sulfur atom, a carbonyl group or an ester group
- Z represents an alkyl group having 1 to 10 carbon atoms.
- alkylamino group examples include methylamino group, ethylamino group, n-propylamino group, i-propylamino group, cyclopropylamino group, n-butylamino group, i-butylamino group, and s-butylamino group.
- T-butylamono group cyclobutylamino group, 1-methyl-cyclopropylamino group, 2-methyl-cyclopropylamino group, n-pentylamino group, 1-methyl-n-butylamino group, 2-methyl-n -Butylamino group, 3-methyl-n-butylamino group, 1,1-dimethyl-n-propylamino group and the like.
- the hydroxy group-containing aromatic methylol compound (B) having the structure of the formula (1) can be exemplified below.
- Hydroxy group-containing aromatic methylol compound (B) is 2-hydroxybenzyl alcohol, 3-hydroxybenzyl alcohol, 4-hydroxybenzyl alcohol, 2,6-di-tert-butyl-4-hydroxymethylphenol, 3-hydroxy-4 -Methoxybenzyl alcohol, 4-hydroxy-3-methoxybenzyl alcohol, 4-hydroxy-3-methoxy- ⁇ -methylbenzyl alcohol, 3-hydroxy- ⁇ -methylbenzyl alcohol, 2-hydroxy-3-methoxybenzyl alcohol, 5 -Bromo-2-hydroxybenzyl alcohol, DL-4-hydroxymandelonitrile, synephrine, (4-hydroxyphenyl) diphenylmethanol, 3,4-dihydroxybenzyl alcohol, 3,5-dihydroxybenzyl It is preferable that the alcohol.
- aromatic compound (A) containing an aromatic ring examples include aromatic amines and phenolic hydroxy group-containing compounds.
- the aromatic amine is preferably an amine having 6 to 40 carbon atoms, and examples thereof include aniline, naphthylamine, phenylnaphthylamine, phenylindole, and carbazole. Phenylnaphthylamine and phenylindole can be preferably used.
- phenolic hydroxy group-containing compound examples include those having 6 to 40 carbon atoms, such as phenol, dihydroxybenzene, trihydroxybenzene, hydroxynaphthalene, dihydroxynaphthalene, or trihydroxynaphthalene, tris (4-hydroxyphenyl) methane, Examples include tris (4-hydroxyphenyl) ethane and 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane.
- Examples of the structure (C) obtained by the reaction between the aromatic ring of the aromatic compound (A) and the hydroxy group-containing aromatic methylol compound (B) include a resin having the structure of the formula (2).
- Ar 1 , R 1 , R 2 and m are the same as those in the formula (1), and A 1 is an aromatic ring of the aromatic compound (A) or an aromatic ring of a novolac resin.
- Ar 1 represents an aryl group having 6 to 40 carbon atoms
- R 1 represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms
- An aryl group having 6 to 40 carbon atoms, a hydroxy group, a cyano group, a nitro group, an amino group, a carboxyl group, an acetyl group, a halogenomethyl group, a -YZ group, a halogen atom, or a combination thereof is shown.
- Y represents an oxygen atom, a sulfur atom, a carbonyl group, or an ester group
- Z represents an alkyl group having 1 to 10 carbon atoms.
- R 2 represents a hydrogen atom or a methyl group.
- R 3 and R 4 each represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cyano group, or an alkylamino group.
- m is an integer of 0 to (4 + 2n)
- n represents the degree of condensation of the benzene ring of the aryl group Ar 1 .
- the reaction between the aromatic compound (A) containing an aromatic ring and the hydroxy group-containing aromatic methylol compound (B) is obtained by changing the above (A) and the above (B) from 1: 0.1 to 8.0, or 1 : It is preferable to react at a molar ratio of 0.1 to 4.0.
- the aromatic compound (A) is a component for constituting the structure (C) contained in the novolac resin.
- the aromatic compound (A) can be an aromatic amine or a phenolic hydroxy group-containing compound.
- Aromatic amines include phenylindole and phenylnaphthylamine.
- the phenolic hydroxy group-containing compounds are phenol, dihydroxybenzene, trihydroxybenzene, hydroxynaphthalene, dihydroxynaphthalene, trihydroxynaphthalene, tris (4-hydroxyphenyl) methane, tris (4-hydroxyphenyl) ethane, 1,1,2, Examples include 2-tetrakis (4-hydroxyphenyl) ethane.
- the novolak resin can be obtained from any aldehyde or ketone that can react with the aromatic compound (A) containing an aromatic ring.
- aldehydes or ketones include those having 6 to 40 carbon atoms, such as benzaldehyde, naphthaldehyde, phenylbenzaldehyde, and pyrenecarboxaldehyde, preferably naphthaldehyde and pyrenecarboxaldehyde.
- the condensation reaction of novolakization and the addition reaction of the hydroxy group-containing aromatic methylol compound (B) proceed simultaneously.
- the acid catalyst used in these reactions include mineral acids such as sulfuric acid, phosphoric acid, perchloric acid, p- Toluenesulfonic acid, p-toluenesulfonic acid monohydrate, organic sulfonic acids such as methanesulfonic acid, and carboxylic acids such as formic acid and oxalic acid are used.
- the amount of the acid catalyst used is variously selected depending on the type of acids used.
- 0.001 to 10000 parts by mass preferably 0.01 to 1000 parts by mass, more preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of the aromatic compound (A) containing an aromatic ring. It is.
- the above condensation reaction and addition reaction are carried out without solvent, but are usually carried out using a solvent. Any solvent that does not inhibit the reaction can be used.
- ethers such as 1,2-dimethoxyethane, diethylene glycol dimethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane and the like can be mentioned.
- the acid catalyst used is a liquid such as formic acid, it can also serve as a solvent.
- the reaction temperature during the condensation is usually 40 ° C to 200 ° C.
- the reaction time is variously selected depending on the reaction temperature, but is usually about 30 minutes to 50 hours.
- the weight average molecular weight Mw of the polymer obtained as described above is usually 500 to 1000000, or 600 to 200000.
- the novolak resin containing the structure (C) obtained by the reaction of the aromatic compound (A) containing an aromatic ring and the hydroxy group-containing aromatic methylol compound (B) can be shown as a typical example below. .
- the resist underlayer film forming composition of the present invention can contain a crosslinking agent component.
- the cross-linking agent include melamine type, substituted urea type, or polymer type thereof.
- a cross-linking agent having at least two cross-linking substituents methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzogwanamine, butoxymethylated benzogwanamine, Compounds such as methoxymethylated urea, butoxymethylated urea, or methoxymethylated thiourea.
- the condensate of these compounds can also be used.
- crosslinking agent a crosslinking agent having high heat resistance
- a compound containing a crosslinking-forming substituent having an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule can be preferably used.
- Examples of this compound include a compound having a partial structure of the following formula (4) and a polymer or oligomer having a repeating unit of the following formula (5).
- R 11 , R 12 , R 13 , and R 14 are a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and the above examples can be used for these alkyl groups.
- the above compounds can be obtained as products of Asahi Organic Materials Co., Ltd. and Honshu Chemical Industry Co., Ltd.
- the compound of the formula (4-24) can be obtained as Asahi Organic Materials Co., Ltd., trade name TM-BIP-A.
- the amount of the crosslinking agent to be added varies depending on the coating solvent used, the base substrate used, the required solution viscosity, the required film shape, etc., but is 0.001 to 80% by mass with respect to the total solid content, preferably The amount is 0.01 to 50% by mass, more preferably 0.05 to 40% by mass.
- cross-linking agents may cause a cross-linking reaction by self-condensation, but when a cross-linkable substituent is present in the above-mentioned polymer of the present invention, it can cause a cross-linking reaction with those cross-linkable substituents.
- an acid and / or an acid generator can be added as a catalyst for promoting the crosslinking reaction.
- p-toluenesulfonic acid trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, 5-sulfosalicylic acid, 4-phenolsulfonic acid, camphorsulfonic acid, 4-chlorobenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalene Acidic compounds such as sulfonic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid, and / or 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, etc.
- a thermal acid generator such as an organic sulfonic acid alkyl ester can be blended.
- the blending amount is 0.0001 to 20% by mass, preferably 0.0005 to 10% by mass, and more preferably 0.01 to 3% by mass with respect to the total solid content.
- a photoacid generator can be added in order to match the acidity with the photoresist coated on the upper layer in the lithography process.
- Preferred photoacid generators include, for example, onium salt photoacid generators such as bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s.
- -Halogen-containing compound photoacid generators such as triazine, and sulfonic acid photoacid generators such as benzoin tosylate and N-hydroxysuccinimide trifluoromethanesulfonate.
- the photoacid generator is 0.2 to 10% by mass, preferably 0.4 to 5% by mass, based on the total solid content.
- the light absorbing agent examples include commercially available light absorbing agents described in “Technical Dye Technology and Market” (published by CMC) and “Dye Handbook” (edited by the Society of Synthetic Organic Chemistry), such as C.I. 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. I. D isperse Orange 1, 5, 13, 25, 29, 30, 31, 44, 57, 72 and 73; I. Disperse Red 1, 5, 7, 13, 17, 19, 43, 50, 54, 58, 65, 72, 73, 88, 117, 137, 143, 199 and 210; I.
- Disperse Violet 43; C.I. I. Disperse Blue 96; C.I. I. FluorescentesBrightening Agent 112, 135 and 163; I. Solvent Orange 2 and 45; I. Solvent Red 1, 3, 8, 23, 24, 25, 27 and 49; I. Pigment Green 10; C.I. I. Pigment Brown 2 or the like can be preferably used.
- the above light-absorbing agent is usually blended in a proportion of 10% by mass or less, preferably 5% by mass or less, based on the total solid content of the resist underlayer film material for lithography.
- the rheology modifier mainly improves the fluidity of the resist underlayer film forming composition, and improves the film thickness uniformity of the resist underlayer film and the fillability of the resist underlayer film forming composition inside the hole, particularly in the baking process. It is added for the purpose of enhancing.
- phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, butyl isodecyl phthalate, adipic acid derivatives such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decyl adipate
- maleic acid derivatives such as normal butyl maleate, diethyl maleate and dinonyl maleate
- oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate
- stearic acid derivatives such as normal butyl stearate and glyceryl stearate. it can.
- These rheology modifiers are usually blended at a ratio of less than 30% by mass with respect to the total solid content of the resist underlayer film material for
- the adhesion auxiliary agent is added mainly for the purpose of improving the adhesion between the substrate or resist and the resist underlayer film forming composition, and preventing the resist from being peeled off particularly during development.
- Specific examples include chlorosilanes such as trimethylchlorosilane, dimethylmethylolchlorosilane, methyldiphenylchlorosilane, chloromethyldimethylchlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylolethoxysilane, diphenyldimethoxysilane, Alkoxysilanes such as enyltriethoxysilane, hexamethyldisilazane, N, N′-bis (trimethylsilyl) urea, silazanes such as dimethyltrimethylsilylamine, trimethylsilylimidazole, methyloltrichlorosilane, ⁇ -chloroprop
- a surfactant can be blended in order to further improve the applicability to surface unevenness.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol ether.
- Polyoxyethylene alkyl allyl ethers Polyoxyethylene alkyl allyl ethers, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate, etc.
- Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as tan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, F-top EF301, EF303, EF352 (trade name, manufactured by Tochem Products Co., Ltd.), MegaFuck F171, F173, R-40, R-40N, R-30N, R-40LM (trade name, manufactured by DIC Corporation), Florard FC430, FC431 (Trade name) manufactured by Sumitomo 3M Co., Ltd., fluorine surfactants such as Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (trade name, manufactured by Asahi Glass Co., Ltd.) Organoshiroki And Sunpolymer KP34
- the blending amount of these surfactants is usually 2.0% by mass or less, preferably 1.0% by mass or less, based on the total solid content of the resist underlayer film material for lithography of the present invention.
- These surfactants may be added alone or in combination of two or more.
- the solvent for dissolving the polymer and the crosslinking agent component, the crosslinking catalyst and the like include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve 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, 2-hydroxypropionic acid Ethyl, 2-hydroxy-2 Ethyl methyl propionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxypropionic acid
- organic solvents are used alone or in combination of two or more.
- high boiling point solvents such as propylene glycol monobutyl ether and propylene glycol monobutyl ether acetate can be mixed and used.
- propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, cyclohexanone and the like are preferable for improving the leveling property.
- propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate are preferable.
- the resin used in the present invention exhibits high solubility in solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate generally used in the lithography process.
- the resist used in the present invention is a photoresist or an electron beam resist.
- the photoresist applied on the upper part of the resist underlayer film for lithography in the present invention either negative type or positive type can be used, and a positive type photoresist composed of a novolak resin and 1,2-naphthoquinonediazide sulfonic acid ester, depending on the acid.
- Chemically amplified photoresist comprising a binder having a group that decomposes to increase the alkali dissolution rate and a photoacid generator, a low molecular weight compound and photoacid that increases the alkali dissolution rate of the photoresist by decomposition with an alkali-soluble binder and acid
- Chemically amplified photoresist comprising a generator, comprising a binder having a group that decomposes with acid to increase the alkali dissolution rate, a low-molecular compound that decomposes with acid to increase the alkali dissolution rate of the photoresist, and a photoacid generator Chemically amplified photoresist with Si atoms in the skeleton
- a photoresist or the like which, for example, Rohm & Haas Co., and a trade name APEX-E.
- an acid is generated by irradiation of a resin containing an Si-Si bond in the main chain and an aromatic ring at the terminal and an electron beam.
- a composition comprising an acid generator, or a composition comprising a poly (p-hydroxystyrene) having a hydroxy group substituted with an organic group containing N-carboxyamine, and an acid generator that generates an acid upon irradiation with an electron beam.
- the acid generated from the acid generator by electron beam irradiation reacts with the N-carboxyaminoxy group of the polymer side chain, and the polymer side chain decomposes into a hydroxy group and exhibits alkali solubility, thus exhibiting alkali development. It dissolves in the liquid to form a resist pattern.
- Acid generators that generate an acid upon irradiation with this electron beam are 1,1-bis [p-chlorophenyl] -2,2,2-trichloroethane, 1,1-bis [p-methoxyphenyl] -2,2,2 -Halogenated organic compounds such as trichloroethane, 1,1-bis [p-chlorophenyl] -2,2-dichloroethane, 2-chloro-6- (trichloromethyl) pyridine, triphenylsulfonium salts, diphenyliodonium salts, etc. Examples thereof include sulfonic acid esters such as onium salts, nitrobenzyl tosylate, and dinitrobenzyl tosylate.
- Alkali amines, tetramethylammonium hydroxide, tetraethylammonium hydroxide, quaternary ammonium salts such as choline, cyclic amines such as pyrrole and piperidine, and alkaline aqueous solutions such as these can be used.
- an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
- an organic solvent can be used as the developer, for example, methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, amyl acetate, isoamyl acetate, ethyl methoxyacetate, ethyl ethoxyacetate, 2-heptanone, propylene glycol Monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monopropyl ether acetate, diethylene glycol mono Butyl ether acetate, diethylene glycol Monophenyl ether acetate, 2-methoxybutyl acetate, 3-methoxybutyl acetate, 4-methoxy
- the development conditions are appropriately selected from a temperature of 5 to 50 ° C. and a time of 10 to 600 seconds.
- a spinner, a coater, etc. on a substrate for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate
- a substrate for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate
- the resist underlayer film forming composition After applying the resist underlayer film forming composition by an appropriate coating method, it is baked and cured to form a coating type underlayer film.
- the thickness of the resist underlayer film is preferably 0.01 to 3.0 ⁇ m.
- the conditions for baking (curing) after coating are 80 to 400 ° C. and 0.5 to 120 minutes.
- a good resist pattern can be obtained by performing, developing, rinsing and drying. If necessary, heating after irradiation with light or an electron beam (PEB: Post Exposure Bake) can also be performed. Then, the resist underlayer film where the resist has been developed and removed by the above process is removed by dry etching, and a desired pattern can be formed on the substrate.
- PEB Post Exposure Bake
- the exposure light in the photoresist is actinic radiation such as near ultraviolet, far ultraviolet, or extreme ultraviolet (for example, EUV, wavelength 13.5 nm), for example, 248 nm (KrF laser light), 193 nm (ArF laser light), Light having a wavelength such as 157 nm (F 2 laser light) is used.
- the light irradiation can be used without particular limitation as long as it can generate an acid from a photoacid generator, and the exposure dose is 1 to 2000 mJ / cm 2 , or 10 to 1500 mJ / cm 2 , or 50. To 1000 mJ / cm 2 .
- the electron beam irradiation of an electron beam resist can be performed using an electron beam irradiation apparatus, for example.
- a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition a step of forming a resist film thereon, a step of forming a resist pattern by light or electron beam irradiation and development, a resist pattern
- a semiconductor device can be manufactured through a step of etching the resist underlayer film and a step of processing the semiconductor substrate with the patterned resist underlayer film.
- resist underlayer films with high etch rate (fast etching speed) as resist underlayer films for such processes compared to resist underlayer films and resists for lithography, which have a selectivity of dry etching rate close to that of resist
- resist underlayer films and resists for lithography which have a selectivity of dry etching rate close to that of resist
- resist underlayer film for lithography having a low dry etching rate selection ratio
- resist underlayer film for lithography having a low dry etching rate selection ratio
- resist underlayer film for lithography having a low dry etching rate selection ratio compared to a semiconductor substrate.
- such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- a process of making the resist pattern and the resist underlayer film narrower than the pattern width at the time of developing the resist during dry etching of the resist underlayer film has begun to be used.
- a resist underlayer film having a selectivity of a dry etching rate close to that of the resist has been required as a resist underlayer film for such a process.
- such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- the substrate after forming the resist underlayer film of the present invention on the substrate, directly or on the resist underlayer film as needed, after forming one to several layers of coating material on the resist underlayer film, A resist can be applied. As a result, the pattern width of the resist becomes narrow, and even when the resist is thinly coated to prevent pattern collapse, the substrate can be processed by selecting an appropriate etching gas.
- a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition and forming a hard mask by a coating material containing a silicon component or the like or a hard mask (for example, silicon nitride oxide) on the semiconductor substrate.
- a semiconductor device can be manufactured through a step of etching the resist underlayer film with an oxygen-based gas or a hydrogen-based gas and a step of processing a semiconductor substrate with a halogen-based gas with the patterned resist underlayer film.
- the resist underlayer film forming composition for lithography of the present invention has a light absorption site incorporated into the skeleton, so there is no diffused material in the photoresist during heating and drying. Moreover, since the light absorption site has a sufficiently large light absorption performance, the effect of preventing reflected light is high.
- composition for forming a resist underlayer film for lithography of the present invention has high thermal stability, can prevent contamination of the upper layer film by decomposition products during baking, and can provide a margin for the temperature margin of the baking process. is there.
- the resist underlayer film material for lithography has a function of preventing reflection of light depending on process conditions, and further prevents the interaction between the substrate and the photoresist, or a material or photoresist used for the photoresist.
- the film can be used as a film having a function of preventing an adverse effect on a substrate of a substance generated during exposure.
- Example 4 10.00 g of phenyl-1-naphthylamine, 10.50 g of 1-pyrenecarboxaldehyde, 5.39 g of 2,6-di-tert-butyl-4-hydroxymethylphenol, 0.99 g of methanesulfonic acid and 1,4-dioxane 40 0.000 g was added, and the mixture was stirred for 24 hours under reflux in a nitrogen atmosphere.
- the reaction solution was dropped into methanol, and the precipitated resin was filtered and washed, and then dried under reduced pressure at 70 ° C. to obtain 15.58 g of a resin containing the formula (3-6).
- the weight average molecular weight of this resin measured by GPC by standard polystyrene conversion was 2600.
- etching rate The following etchers and etching gases were used for measuring the dry etching rate.
- ES401 manufactured by Nippon Scientific: CF 4
- the resist underlayer film forming composition solutions prepared in Examples 1 to 4 and Comparative Examples 4 and 5 were each applied onto a silicon wafer using a spin coater.
- the resist underlayer film (film thickness: 0.25 ⁇ m) was formed by baking at 400 ° C. for 2 minutes on a hot plate.
- the dry etching rate was measured using CF 4 gas as the etching gas.
- a phenol-novolak resin (commercial product, weight average molecular weight Mw measured in terms of polystyrene by GPC is 2000, polydispersity Mw / Mn is 2.5) is applied onto a silicon wafer using a spin coater. It was applied and baked at 205 ° C. for 1 minute to form a coating film. The dry etching rate was measured using CF 4 gas as the etching gas. Dry etching of resist underlayer films of Examples 1 to 4 and Comparative Examples 4 and 5 when the etching rate of a phenol novolak resin film (film thickness: 0.25 ⁇ m) obtained by baking at 205 ° C.
- the speed ratio is a dry etching speed ratio of (resist underlayer film) / (phenol novolac resin film).
- the hydroxy group-containing aromatic methylol compound (B) needs to contain a hydroxy group.
- (B) does not contain a hydroxy group
- the solubility in a solvent is insufficient.
- the novolak resin is produced using an aldehyde in which the aromatic compound (A) contains a hydroxy group (Comparative Example 4)
- a structure in which a hydroxy group is present in the side chain extending from the novolak polymer main chain is present, and dry etching is performed. The speed increases and the performance as a hard mask decreases.
- the polymer used in the present invention is considered that the hydroxy group-containing aromatic methylol compound (B) is present at the end of the novolak resin, and by using a polymer having such a structure, the solubility in a solvent is improved. In addition, the dissolution failure that causes foreign matters when applied to the substrate is prevented, and the lower layer film obtained by curing after the application exhibits high etching resistance and has good hard mask characteristics.
- the resist underlayer film material used in the lithography process using the multilayer film of the present invention not only has high dry etching resistance and antireflection film function, but also has high solubility in a resist solvent (solvent used for lithography).
- excellent spin coatability the resulting resist underlayer film has no intermixing (layer mixing) with the overcoat resist, and suppresses the occurrence of wiggling (irregular pattern bending) of the resist underlayer film during the dry etching process. Fine substrate processing is achieved.
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Abstract
Description
ポリメチロールカルバゾールを用いたレジスト下層膜形成組成物が開示されている(特許文献1、特許文献2、及び特許文献3参照)。
フルオレンフェノールノボラック樹脂を用いたレジスト下層膜形成組成物が開示されている(特許文献4参照)。
フルオレンナフトールノボラック樹脂を用いたレジスト下層膜形成組成物が開示されている(特許文献5参照)。
フルオレンフェノールとアリールアルキレンを繰り返し単位とする樹脂を含むレジスト下層膜形成組成物が開示されている(特許文献6及び特許文献7参照)。
カルバゾールノボラックを用いたレジスト下層膜形成組成物が開示されている(特許文献8参照)。
多核フェノールノボラックを用いたレジスト下層膜形成組成物が開示されている(特許文献9参照)。
第2観点として、前記芳香族化合物(A)がノボラック樹脂に含まれる構造体(C)を構成するための成分である第1観点に記載のレジスト下層膜形成組成物、
第3観点として、前記ヒドロキシ基含有芳香族メチロール化合物(B)が式(1):
第4観点として、前記ヒドロキシ基含有芳香族メチロール化合物(B)が2-ヒドロキシベンジルアルコール、4-ヒドロキシベンジルアルコール、又は2,6-ジ-tert-ブチル-4-ヒドロキシメチルフェノールである第1観点乃至第3観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第5観点として、前記構造体(C)が式(2):
第6観点として、前記芳香族化合物(A)が芳香族アミン又はフェノール性ヒドロキシ基含有化合物である第1観点乃至第5観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第7観点として、前記ノボラック樹脂が、芳香族アミン又はフェノール性ヒドロキシ基含有化合物と、アルデヒド又はケトンとの反応により生成した樹脂である第1観点乃至第6観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第8観点として、前記芳香族アミンが、フェニルインドール又はフェニルナフチルアミンである第7観点に記載のレジスト下層膜形成組成物、
第9観点として、前記フェノール性ヒドロキシ基含有化合物がフェノール、ジヒドロキシベンゼン、トリヒドロキシベンゼン、ヒドロキシナフタレン、ジヒドロキシナフタレン、トリヒドロキシナフタレン、トリス(4-ヒドロキシフェニル)メタン、トリス(4-ヒドロキシフェニル)エタン、又は1,1,2,2-テトラキス(4-ヒドロキシフェニル)エタンである第7観点に記載のレジスト下層膜形成組成物、
第10観点として、前記アルデヒドが、ナフトアルデヒド又はピレンカルボキシアルデヒドである第7観点乃至第9観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第11観点として、更に溶剤を含む第1観点乃至第10観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第12観点として、更に酸及び/又は酸発生剤を含む第1観点乃至第11観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第13観点として、更に架橋剤を含む第1観点乃至第12観点のうちいずれか一つに記載のレジスト下層膜形成組成物、
第14観点として、第1観点乃至第13観点のうちいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成して下層膜を形成する工程を含む半導体の製造に用いられるレジストパターンの形成方法、
第15観点として、半導体基板上に第1観点乃至第13観点のうちいずれか一つに記載のレジスト下層膜形成組成物により下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、該レジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法、
第16観点として、半導体基板上に第1観点乃至第13観点のうちいずれか一つに記載のレジスト下層膜形成組成物により下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、該レジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法、並びに
第17観点として、前記ハードマスクが無機物の蒸着膜からなる第16観点に記載の製造方法、である。
特に、本発明のレジスト下層膜形成組成物は、レジスト溶剤への溶解性が高く、スピンコート性に優れた塗布型組成物である。そして、本発明のレジスト下層膜形成組成物から得られたレジスト下層膜は、被膜して焼成後、それらレジスト溶剤に再溶解することはない。
式(1)中、Ar1は炭素原子数6乃至40のアリール基を示し、R1は炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数2乃至10のアルキニル基、炭素原子数6乃至40のアリール基、ヒドロキシ基、シアノ基、ニトロ基、アミノ基、カルボキシル基、アセチル基、ハロゲノメチル基、-Y-Z基、ハロゲン原子、またはそれらの組み合わせを示す。Yは酸素原子、硫黄原子、カルボニル基、エステル基を示し、Zは炭素原子数1乃至10のアルキル基を示す。R2は水素原子又はメチル基を示す。R3、R4はそれぞれ水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、シアノ基、又はアルキルアミノ基を示す。mは0乃至(4+2n)の整数であり、nはアリール基Ar1が有するベンゼン環の縮合度を示す。
芳香族アミンとしては炭素原子数6乃至40のアミンが好ましく、例えばアニリン、ナフチルアミン、フェニルナフチルアミン、フェニルインドール、及びカルバゾールが例示される。フェニルナフチルアミン、及びフェニルインドールは好適に用いることができる。
フェノール性ヒドロキシ基含有化合物としては炭素原子数6乃至40のものが挙げられ、例えばフェノール、ジヒドロキシベンゼン、トリヒドロキシベンゼン、ヒドロキシナフタレン、ジヒドロキシナフタレン、又はトリヒドロキシナフタレン、トリス(4-ヒドロキシフェニル)メタン、トリス(4-ヒドロキシフェニル)エタン、1,1,2,2-テトラキス(4-ヒドロキシフェニル)エタンが例示される。
式(2)中、Ar1、R1、R2、mは式(1)と同じであり、A1は芳香族化合物(A)の芳香族環又はノボラック樹脂の芳香族環である。
即ち、Ar1は炭素原子数6乃至40のアリール基を示し、R1は炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数2乃至10のアルキニル基、炭素原子数6乃至40のアリール基、ヒドロキシ基、シアノ基、ニトロ基、アミノ基、カルボキシル基、アセチル基、ハロゲノメチル基、-Y-Z基、ハロゲン原子、またはそれらの組み合わせを示す。Yは酸素原子、硫黄原子、カルボニル基、エステル基を示し、Zは炭素原子数1乃至10のアルキル基を示す。R2は水素原子又はメチル基を示す。R3、R4はそれぞれ水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、シアノ基、又はアルキルアミノ基を示す。mは0乃至(4+2n)の整数であり、nはアリール基Ar1が有するベンゼン環の縮合度を示す。
芳香族アミンはフェニルインドール、フェニルナフチルアミン等が挙げられる。
フェノール性ヒドロキシ基含有化合物はフェノール、ジヒドロキシベンゼン、トリヒドロキシベンゼン、ヒドロキシナフタレン、ジヒドロキシナフタレン、トリヒドロキシナフタレン、トリス(4-ヒドロキシフェニル)メタン、トリス(4-ヒドロキシフェニル)エタン、1,1,2,2-テトラキス(4-ヒドロキシフェニル)エタン等が挙げられる。
アルデヒドもしくはケトン類としては炭素原子数6乃至40のものが挙げられ、例えばベンズアルデヒド、ナフトアルデヒド、フェニルベンズアルデヒド、及びピレンカルボキシアルデヒドが例示され、好ましくはナフトアルデヒド、ピレンカルボキシアルデヒドが挙げられる。
上記の縮合反応と付加反応は無溶剤でも行われるが、通常溶剤を用いて行われる。溶剤としては反応を阻害しないものであれば全て使用することができる。例えば1,2-ジメトキシエタン、ジエチレングリコールジメチルエーテル、プロピレングリコールモノメチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル類が挙げられる。また、使用する酸触媒が例えば蟻酸のような液状のものであるならば溶剤としての役割を兼ねさせることもできる。
縮合時の反応温度は通常40℃乃至200℃である。反応時間は反応温度によって種々選択されるが、通常30分乃至50時間程度である。
以上のようにして得られる重合体の重量平均分子量Mwは、通常500乃至1000000、又は600乃至200000である。
架橋剤の添加量は、使用する塗布溶剤、使用する下地基板、要求される溶液粘度、要求される膜形状などにより変動するが、全固形分に対して0.001乃至80質量%、好ましくは 0.01乃至50質量%、さらに好ましくは0.05乃至40質量%である。これら架橋剤は自己縮合による架橋反応を起こすこともあるが、本発明の上記のポリマー中に架橋性置換基が存在する場合は、それらの架橋性置換基と架橋反応を起こすことができる。
さらに、プロピレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテルアセテート等の高沸点溶剤を混合して使用することができる。これらの溶剤の中でプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、乳酸エチル、乳酸ブチル、及びシクロヘキサノン等がレベリング性の向上に対して好ましい。特にプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテートが好ましい。
また電子線レジストの電子線照射は、例えば電子線照射装置を用い照射することができる。
2-フェニルインドール8.00g、1-ピレンカルボキシアルデヒド5.72g、2-ヒドロキシベンジルアルコール2.06g、メタンスルホン酸0.36gにプロピレングリコールモノメチルエーテル29.96gを加え、窒素雰囲気下、130℃で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、式(3-1)を含む樹脂6.15gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1370であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、プロピレングリコールモノメチルエーテルアセテート13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
2-フェニルインドール8.00g、1-ピレンカルボキシアルデヒド5.72g、4-ヒドロキシベンジルアルコール2.06g、メタンスルホン酸0.36gにプロピレングリコールモノメチルエーテル29.96gを加え、窒素雰囲気下、130℃で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、式(3-2)を含む樹脂5.52gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1100であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、プロピレングリコールモノメチルエーテルアセテート13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
2-フェニルインドール7.50g、1-ピレンカルボキシアルデヒド5.36g、2,6-ジ-tert-ブチル-4-ヒドロキシメチルフェノール3.70g、メタンスルホン酸0.34gにプロピレングリコールモノメチルエーテル31.32gを加え、窒素雰囲気下、130℃で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、式(3-3)を含む樹脂6.45gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1510であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、プロピレングリコールモノメチルエーテルアセテート13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
フェニル-1-ナフチルアミン10.00g、1-ピレンカルボキシアルデヒド10.50g、2、6-ジ-tert-ブチル-4-ヒドロキシメチルフェノール5.39g、メタンスルホン酸0.99gに1,4-ジオキサン40.00gを加え、窒素雰囲気下、還流状態で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、式(3-6)を含む樹脂15.58gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は2600であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにシクロヘキサノン13.30g、プロピレングリコールモノメチルエーテルアセテート5.70gに溶解させ、レジスト下層膜形成組成物を調製した。
2-フェニルインドール8.39g、1-ピレンカルボキシアルデヒド10.00g、メタンスルホン酸0.42gにプロピレングリコールモノメチルエーテル5.64g、プロピレングリコールモノメチルエーテルアセテート22.57gを加え、窒素雰囲気下、130℃で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、下記式(5-1)を含む樹脂15.10gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1200であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、シクロヘキサノン13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
フェニル-1-ナフチルアミン11.00g、1-ピレンカルボキシアルデヒド11.55g、メタンスルホン酸0.48gに1,4-ジオキサン17.27g、トルエン17.27gを加え、窒素雰囲気下、還流状態で16時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、下記式(5-2)を含む樹脂19.88gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は900であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、シクロヘキサノン13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
2-フェニルインドール10.00g、1-ピレンカルボキシアルデヒド7.15g、ベンジルアルコール2.24g、メタンスルホン酸0.45gにプロピレングリコールモノメチルエーテル36.84gを加え、窒素雰囲気下、130℃で22時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、下記式(5-3)を含む樹脂9.70gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1270であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、シクロヘキサノン13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
2-フェニルインドール10.00g、1-ピレンカルボキシアルデヒド7.15g、サリチルアルデヒド2.52g、メタンスルホン酸0.45gにプロピレングリコールモノメチルエーテル37.37gを加え、窒素雰囲気下、130℃で22時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥することで、下記式(5-4)を含む樹脂9.84gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1360であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、シクロヘキサノン13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
m-クレゾール60.00g、37%ホルマリン水溶液27.00g、p-トルエンスルホン酸・1水和物1.60gにプロピレングリコールモノメチルエーテル150gを加え、窒素雰囲気下、還流状態で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥した。次に、この得られた樹脂12.02gに9-アントラセンメタノール4.13g、THF28.80g、p-トルエンスルホン酸・1水和物0.52gを加え、窒素雰囲気下、還流状態で24時間撹拌した。反応液をメタノール中に滴下し、析出した樹脂を濾過、洗浄した後、70℃で減圧乾燥し、下記式(5-5)を含む樹脂2.75gを得た。尚、GPCより標準ポリスチレン換算で測定されるこの樹脂の重量平均分子量は1470であった。
次に、この得られた樹脂1.00g、界面活性剤(DIC(株)製、品名:メガファック〔商品名〕R-40、フッ素系界面活性剤)0.002gにプロピレングリコールモノメチルエーテル5.70g、プロピレングリコールモノメチルエーテルアセテート13.30gに溶解させ、レジスト下層膜形成組成物を調製した。
実施例1乃至実施例4、比較例1乃至比較例3で得られた樹脂を代表的なレジスト溶剤であるプロピレングリコールモノメチルエーテル(PGME)の30質量%溶液を調製した。この際、樹脂が溶解して均一溶液が得られた場合を溶解性「良好」とし、十分に溶解せず懸濁液として得られた場合を溶解性「不良」とした。この樹脂の溶解性試験の結果を表1に表す。
ドライエッチング速度の測定に用いたエッチャ-及びエッチングガスは以下のものを用いた。
ES401(日本サイエンティフィック製):CF4
実施例1~4及び比較例4、5で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で400℃2分間焼成し、レジスト下層膜(膜厚0.25μm)を形成した。エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定した。
また、同様にフェノ-ルノボラック樹脂(市販品、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.5)溶液を、スピンコーターを用いてシリコンウェハー上に塗布し、205℃1分間焼成して塗膜を形成した。エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定した。205℃1分間焼成して得られたフェノールノボラック樹脂膜(膜厚0.25μm)のエッチング速度を1.00とした時の実施例1~4及び比較例4、5のレジスト下層膜のドライエッチング速度と、フェノールノボラック樹脂のドライエッチング速度の比較を行った。結果を表2に示した。速度比は(レジスト下層膜)/(フェノ-ルノボラック樹脂膜)のドライエッチング速度比である。
また、芳香族化合物(A)がヒドロキシ基を含有するアルデヒドを用いてノボラック樹脂を製造した場合(比較例4)は、ノボラックポリマー主鎖から伸びる側鎖にヒドロキシ基が存在した構造となり、ドライエッチング速度が高くなりハードマスクとしての性能が低下する。
Claims (17)
- 芳香族化合物(A)の芳香族環とヒドロキシ基含有芳香族メチロール化合物(B)との反応により得られる構造体(C)を含むノボラック樹脂を含むレジスト下層膜形成組成物。
- 前記芳香族化合物(A)がノボラック樹脂に含まれる構造体(C)を構成するための成分である請求項1に記載のレジスト下層膜形成組成物。
- 前記ヒドロキシ基含有芳香族メチロール化合物(B)が式(1):
- 前記ヒドロキシ基含有芳香族メチロール化合物(B)が2-ヒドロキシベンジルアルコール、4-ヒドロキシベンジルアルコール、又は2,6-ジ-tert-ブチル-4-ヒドロキシメチルフェノールである請求項1乃至請求項3のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 前記芳香族化合物(A)が芳香族アミン又はフェノール性ヒドロキシ基含有化合物である請求項1乃至請求項5のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 前記ノボラック樹脂が、芳香族アミン又はフェノール性ヒドロキシ基含有化合物と、アルデヒド又はケトンとの反応により生成した樹脂である請求項1乃至請求項6のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 前記芳香族アミンが、フェニルインドール又はフェニルナフチルアミンである請求項7に記載のレジスト下層膜形成組成物。
- 前記フェノール性ヒドロキシ基含有化合物がフェノール、ジヒドロキシベンゼン、トリヒドロキシベンゼン、ヒドロキシナフタレン、ジヒドロキシナフタレン、トリヒドロキシナフタレン、トリス(4-ヒドロキシフェニル)メタン、トリス(4-ヒドロキシフェニル)エタン、又は1,1,2,2-テトラキス(4-ヒドロキシフェニル)エタンである請求項7に記載のレジスト下層膜形成組成物。
- 前記アルデヒドが、ナフトアルデヒド又はピレンカルボキシアルデヒドである請求項7乃至請求項9のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 更に溶剤を含む請求項1乃至請求項10のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 更に酸及び/又は酸発生剤を含む請求項1乃至請求項11のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 更に架橋剤を含む請求項1乃至請求項12のうちいずれか1項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項13のうちいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成して下層膜を形成する工程を含む半導体の製造に用いられるレジストパターンの形成方法。
- 半導体基板上に請求項1乃至請求項13のうちいずれか1項に記載のレジスト下層膜形成組成物により下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、該レジストパターンにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 半導体基板上に請求項1乃至請求項13のうちいずれか1項に記載のレジスト下層膜形成組成物により下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、該レジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該下層膜をエッチングする工程、及びパターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 前記ハードマスクが無機物の蒸着膜からなる請求項16に記載の製造方法。
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Also Published As
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KR102417838B1 (ko) | 2022-07-06 |
TWI713462B (zh) | 2020-12-21 |
CN106662819B (zh) | 2021-06-25 |
CN106662819A (zh) | 2017-05-10 |
US11650505B2 (en) | 2023-05-16 |
TW201620981A (zh) | 2016-06-16 |
JPWO2016021594A1 (ja) | 2017-05-25 |
KR20170042500A (ko) | 2017-04-19 |
US20170227850A1 (en) | 2017-08-10 |
JP6703308B2 (ja) | 2020-06-03 |
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