WO2013012068A1 - チタン及びシリコン含有リソグラフィー用薄膜形成組成物 - Google Patents
チタン及びシリコン含有リソグラフィー用薄膜形成組成物 Download PDFInfo
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- WO2013012068A1 WO2013012068A1 PCT/JP2012/068479 JP2012068479W WO2013012068A1 WO 2013012068 A1 WO2013012068 A1 WO 2013012068A1 JP 2012068479 W JP2012068479 W JP 2012068479W WO 2013012068 A1 WO2013012068 A1 WO 2013012068A1
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- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- OAVPBWLGJVKEGZ-UHFFFAOYSA-N tributoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCCCC)(OCCCC)OCCCC)CCC2OC21 OAVPBWLGJVKEGZ-UHFFFAOYSA-N 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- OHKFEBYBHZXHMM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CCC)OCC1CO1 OHKFEBYBHZXHMM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- NLKPPXKQMJDBFO-UHFFFAOYSA-N triethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OCC)(OCC)OCC)CCC2OC21 NLKPPXKQMJDBFO-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- PSUKBUSXHYKMLU-UHFFFAOYSA-N triethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OCC)(OCC)OCC)CCC2OC21 PSUKBUSXHYKMLU-UHFFFAOYSA-N 0.000 description 1
- GSUGNQKJVLXBHC-UHFFFAOYSA-N triethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCOCC1CO1 GSUGNQKJVLXBHC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZSOVVFMGSCDMIF-UHFFFAOYSA-N trimethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OC)(OC)OC)=CC=CC2=C1 ZSOVVFMGSCDMIF-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- GDRDDMTUPOZHSD-UHFFFAOYSA-N trimethoxy-(4-phenylphenyl)silane Chemical compound C1=CC([Si](OC)(OC)OC)=CC=C1C1=CC=CC=C1 GDRDDMTUPOZHSD-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-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
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-UHFFFAOYSA-N 0.000 description 1
- GUKYSRVOOIKHHB-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCOCC1CO1 GUKYSRVOOIKHHB-UHFFFAOYSA-N 0.000 description 1
- ZMYLTZKFSOCRDP-UHFFFAOYSA-N trimethoxy-[6-(methoxymethoxy)naphthalen-2-yl]silane Chemical compound C1=C([Si](OC)(OC)OC)C=CC2=CC(OCOC)=CC=C21 ZMYLTZKFSOCRDP-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
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Images
Classifications
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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
-
- 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
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—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
-
- 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
- H01L21/31127—Etching organic layers
- H01L21/31133—Etching organic layers by chemical means
- H01L21/31138—Etching organic layers by chemical means by dry-etching
Definitions
- the present invention relates to a composition for forming a lower layer film between a substrate and a resist (for example, a photoresist, an electron beam resist, and an EUV resist) used for manufacturing a semiconductor device.
- a resist for example, a photoresist, an electron beam resist, and an EUV resist
- the present invention also relates to a composition for forming a thin film that covers an upper layer of an EUV resist and absorbs light outside the EUV band.
- microfabrication by lithography using a photoresist has been performed in the manufacture of semiconductor devices.
- the microfabrication is obtained by forming a thin film of photoresist on a semiconductor substrate such as a silicon wafer, irradiating it with an actinic ray such as ultraviolet rays through a mask pattern on which a semiconductor device pattern is drawn, and developing it.
- an actinic ray such as ultraviolet rays
- fine irregularities corresponding to the pattern are formed on the substrate surface by etching the substrate using the photoresist pattern as a protective film.
- a film known as a hard mask containing a metal element such as silicon or titanium is used (for example, see Patent Document 1 and Patent Document 2). ).
- the rate of removal by dry etching largely depends on the type of gas used for dry etching. Then, by appropriately selecting the gas type, it is possible to remove the hard mask by dry etching without greatly reducing the thickness of the photoresist.
- a resist underlayer film has been disposed between a semiconductor substrate and a photoresist in order to achieve various effects including an antireflection effect.
- studies have been made on compositions for resist underlayer films.
- development of new materials for resist underlayer films is desired because of the variety of required characteristics.
- An object of the present invention is to provide a thin film forming composition used together with a resist (photoresist, electron beam resist, EUV resist) in a lithography process that can be used for manufacturing a semiconductor device. Specifically, it is to provide a resist underlayer film forming composition for lithography for forming a resist underlayer film that can be used as a hard mask. Moreover, it is providing the resist underlayer film forming composition for lithography for forming the resist underlayer film which can be used as an antireflection film. Another object of the present invention is to provide a resist underlayer film for lithography that does not cause intermixing with the resist and has a higher dry etching rate than the resist, and a resist underlayer film forming composition for forming the underlayer film.
- An object of the present invention is to provide a composition for forming an upper layer film of an EUV resist that is intended to suppress a decrease in sensitivity of the EUV resist due to wavelength light and a deterioration in pattern shape.
- the present invention is to provide an EUV resist underlayer film (hard mask) as a thin film existing under the EUV resist and a solvent underlayer resist underlayer film forming composition. Furthermore, it is to provide a reverse material.
- the present invention provides a resist underlayer film forming composition such as a photoresist, a resist underlayer film forming composition such as an EUV resist, an EUV resist upper layer film forming composition, a reverse material forming composition, and a solvent developing resist underlayer film formation. It is providing the thin film formation composition which can be utilized for a composition etc.
- R 0 has an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group.
- An organic group which is an organic group and bonded to a titanium atom by a Ti—C bond, and R 1 represents an alkoxy group, an acyloxy group, or a halogen atom.
- a represents an integer of 0 to 2.
- R 3 represents an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group Or an organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group and bonded to a silicon atom by a Si—C bond or a Si—N bond
- 4 represents an alkoxy group, an acyloxy group, or a halogen atom.
- a ′ represents an integer of 1
- b represents an integer of 0 or 1
- (a ′ + b) represents an integer of 1 or 2.
- a hydrolyzate of the mixture, or a hydrolyzed condensate of the mixture, which is converted to Ti atoms and Si atoms in the composition is converted to Ti atoms and Si atoms in the composition.
- the thin film forming composition includes a titanium compound (A) selected from the group consisting of a compound represented by the above formula (1), a titanium chelate compound, and a hydrolyzable titanium dimer, and the above formula (2).
- R 5 represents an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, a sulfonyl group, or a sulfide bond.
- a ′′ represents an integer of 0 to 3.
- a thin film-forming composition according to the first aspect comprising a mixture with a silicon compound (C) represented by (1), a hydrolyzate of the mixture, or a hydrolysis condensate of the mixture,
- the nitrogen atom-containing cyclic group or the organic group containing the same is represented by the formula (4): [In the formula (4), R 7 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, an alkenyl group, an epoxy group, a sulfonyl group, or an organic group containing them, and R 8 represents 1 to 1 carbon atoms.
- R 9 to R 13 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group, an epoxy group, or a sulfonyl group. Or an organic group containing them.
- ⁇ Represents a group represented by A thin film forming composition according to the first aspect or the second aspect, wherein the organic group is an organic group bonded to a silicon atom by a Si—C bond.
- the thin film forming composition according to the first aspect or the second aspect wherein the nitrogen atom-containing cyclic group or the organic group containing the nitrogen group is an imidazole group or an organic group containing an imidazole group
- the thin film forming composition according to the first aspect or the second aspect wherein the condensed aromatic ring group or the organic group containing the condensed aromatic ring group is a naphthyl group or an anthryl group
- the thin film forming composition according to the first aspect or the second aspect wherein the protected phenolic hydroxy group or the organic group containing the same is an alkoxyalkyl-substituted aryl group or an alkoxyalkoxyalkyl-substituted aryl group
- the thin film forming composition according to the first aspect or the second aspect wherein the bisaryl group or the organic group containing the bisaryl group is a bisphenyl group
- a step of applying the thin film forming composition according to any one of the first aspect to the eleventh aspect on a semiconductor substrate and baking to form a thin film, and forming a resist composition on the thin film A step of coating to form a resist film, a step of exposing the resist film, a step of developing the resist film after exposure to obtain a resist pattern, a step of etching a thin film with the resist pattern, and a patterned resist film
- a method of manufacturing a semiconductor device including a step of processing a semiconductor substrate with a thin film;
- a step of forming an organic underlayer film on a semiconductor substrate, the thin film forming composition according to any one of the first aspect to the eleventh aspect is applied on the organic underlayer film, and fired to form a thin film
- a method of manufacturing a conductor arrangement As a sixteenth aspect, a step of forming a resist pattern on a substrate, a step of applying the thin film forming composition according to any one of the first aspect to the eleventh aspect on the substrate, and baking to form a thin film; Etching the thin film to expose the resist surface, etching the resist pattern, and reversing the pattern.
- the manufacturing method according to any one of the thirteenth aspect to the sixteenth aspect, in which the resist is an EUV resist
- a method of manufacturing a semiconductor device including a step of forming a thin film by applying a thin film forming composition, a step of exposing with EUV, a step of developing an EUV resist after exposure to obtain a resist pattern, and a step of processing a semiconductor substrate with the resist pattern is there.
- the thin film is formed on a substrate by a coating method, or the thin film is formed thereon by an organic underlayer film on the substrate, and a resist film (for example, a photoresist, Electron beam resist, EUV resist) is formed.
- a resist film for example, a photoresist, Electron beam resist, EUV resist
- a resist pattern is formed by exposure and development, the pattern is transferred by dry etching the thin film using the resist pattern, and the substrate is processed by the pattern, or the organic underlayer film is transferred by etching.
- the substrate is processed by the organic underlayer film.
- the resist film thickness tends to be thin in order to prevent pattern collapse.
- dry etching for transferring a pattern to a film existing in a lower layer by reducing the thickness of the resist, the pattern cannot be transferred unless the etching rate is higher than that of the upper layer.
- a thin film (containing an inorganic titanium-silicon compound) of the present invention is coated on a substrate with or without an organic underlayer film, and a resist film (organic resist) is formed thereon. Film).
- the organic component film and the inorganic component film differ greatly in the dry etching rate depending on the selection of the etching gas.
- the organic component film has an oxygen-based gas and the dry etching rate increases.
- the inorganic component film has a halogen-containing gas. This increases the dry etching rate.
- a resist pattern is formed, and the thin film of the present invention present in the lower layer is dry-etched with a halogen-containing gas, the pattern is transferred to the thin film, and the substrate is processed using the halogen-containing gas with the pattern transferred to the thin film I do.
- a thin film that has been transferred dry-etch the underlying organic underlayer with an oxygen-based gas, transfer the pattern onto the organic underlayer, and then transfer the halogen-containing gas to the patterned underlayer. Use to process the substrate.
- the thin film has a hard mask function as a resist underlayer film, and an alkoxy group or an acyloxy group (acyloxy group) in the structure of the compound represented by the above formulas (1), (2) and (3).
- Hydrolyzable groups such as halogen groups can be hydrolyzed or partially hydrolyzed, and then subjected to a condensation reaction of hydroxy groups to produce polytitanoxane (Ti—O—Ti structure), polyorganosiloxane (Si—O—Si structure), A copolymer of Ti—O—Si structure is produced.
- the thin film of the present invention contains a copolymer polymer having a Ti—O—Si structure as a main component, but contains polytitanoxane (Ti—O—Ti structure) and polyorganosiloxane (Si—O—Si structure). Also good. These structures have a sufficient antireflection function and a sufficient hard mask function.
- the inorganic polymer (intermediate film) is effective as a hard mask for the etching of the organic underlayer film existing thereunder and the processing (etching) of the substrate. That is, it has sufficient dry etching resistance against oxygen dry etching gas of the organic underlayer film during substrate processing.
- the thin film of the present invention has an improvement in the dry etching rate with respect to these upper layer resists and resistance to dry etching during substrate processing.
- the thin film forming composition of the present invention selectively transmits only EUV as an upper layer film of the EUV resist without intermixing with the EUV resist and blocking unwanted exposure light such as UV and DUV during EUV exposure.
- it can be used as a film forming composition for the upper layer of an EUV resist that can be developed with a developer after exposure.
- the EUV light Upon exposure of the EUV resist, the EUV light is radiated with UV light or DUV light together with the EUV light.
- This EUV light contains about 5% of light having a wavelength of 300 nm or less in addition to EUV light. However, for example, light having a wavelength of 190 to 300 nm, 190 to 250 nm, particularly 200 to 240 nm is likely to reduce the sensitivity of the EUV resist and the pattern shape. Connected. When the line width is 22 nm or less, the influence of the UV light or DUV light (OUT of BAND / out-of-band radiation) starts to appear, and the resolution of the EUV resist is adversely affected.
- the process is complicated.
- 200-240 nm of unwanted DUV light is absorbed by the thin film on the resist upper layer to improve the resolution of the EUV resist.
- the titanium oxide selectively absorbs the DUV light in the vicinity of 200 to 240 nm
- the inorganic polymer used for the thin film of the upper layer of the EUV resist preferably contains titanium oxide. And since it can melt
- the lower layer reflection of the EUV resist that can prevent reflection from undesirable exposure light, for example, the above-described UV or DUV substrate or interface, without intermixing with the EUV resist.
- the thin film-forming composition of the present invention can be used. Reflection can be efficiently prevented in the lower layer of the EUV resist.
- the thin film forming composition of the present invention can be used as a reverse material.
- the reverse material is formed by coating the thin film forming composition of the present invention on a resist pattern formed on a substrate and drying it. Then, the thin film is etched back to expose the resist pattern surface, and is used as a reverse material that reverses the pattern by dry etching with a gas (for example, oxygen-based gas) that can selectively remove the resist to leave only the thin film layer. be able to.
- a gas for example, oxygen-based gas
- FIG. 1 is an electron micrograph of a cross section of a resist pattern obtained in Example 1.
- FIG. FIG. 2 is an electron micrograph of the cross section of the resist pattern obtained in Comparative Example 1.
- the present invention includes a titanium compound (A) selected from the group consisting of a compound represented by the above formula (1), a titanium chelate compound, and a hydrolyzable titanium dimer, and a silicon compound represented by the above formula (2) ( B), a hydrolyzate of the mixture, or a hydrolyzate condensate of the mixture, wherein the Ti atom is based on the total number of moles converted to Ti atom and Si atom in the composition.
- a thin film forming composition used together with a resist in a lithography process in which the number of moles is 50% to 90%, preferably 55% to 90%, more preferably 60% to 90%.
- the present invention also provides a titanium compound (A) selected from the group consisting of a compound represented by the above formula (1), a titanium chelate compound, and a hydrolyzable titanium dimer, and a silicon represented by the above formula (2).
- a composition comprising a mixture of the compound (B) and the silicon compound (C) represented by the above formula (3), a hydrolyzate of the mixture, or a hydrolysis condensate of the mixture,
- the number of moles of Ti atoms is 50 to 90%, preferably 55% to 90%, more preferably 60% to 90% with respect to the total number of moles converted to Ti atoms and Si atoms in the resist. It is a thin film forming composition used together.
- the thin film forming composition of the present invention is represented by the above formula (2), a titanium compound (A) selected from the group consisting of a compound represented by the above formula (1), a titanium chelate compound, and a hydrolyzable titanium dimer.
- acid, water, alcohol, curing catalyst, acid generator, other organic polymer, light-absorbing compound, surfactant and the like can be included.
- the solid content in the thin film forming composition of the present invention is, for example, 0.1 to 50% by mass, or 0.1% by mass 30% by mass, or 0.1% by mass 25% by mass.
- the solid content is obtained by removing the solvent component from all the components of the thin film forming composition.
- the proportion of hydrolyzable titanium, hydrolyzable organosilane, hydrolyzate thereof, and hydrolyzed condensate thereof in the solid content is 20% by mass or more, for example, 50 to 100% by mass, or 60 to 100% by mass. %, Or 70 to 100% by mass.
- R 0 is an alkyl group, aryl group, halogenated alkyl group, halogenated aryl group, alkenyl group, or An organic group having an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group and bonded to a titanium atom by a Ti—C bond.
- R 1 represents an alkoxy group, an acyloxy group, or a halogen atom.
- a represents an integer of 0 to 2.
- the compound represented by the formula (1) can be preferably used when a is 0.
- alkyl group examples include straight-chain or branched alkyl groups having 1 to 10 carbon atoms such as a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i- Butyl, s-butyl, t-butyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n-butyl, 1,1-dimethyl -N-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, n-hexyl group, 1-methyl-n-pentyl group 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2-dimethyl-n-butyl group, 1,
- the alkyl group may be a cyclic alkyl group.
- the cyclic alkyl group having 1 to 10 carbon atoms may be a cyclopropyl group, a cyclobutyl group, a 1-methyl-cyclopropyl group, or a 2-methyl-cyclopropyl group.
- cyclopentyl group 1-methyl-cyclobutyl group, 2-methyl-cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,3-dimethyl-cyclopropyl group, 1-ethyl- Cyclopropyl group, 2-ethyl-cyclopropyl group, cyclohexyl group, 1-methyl-cyclopentyl group, 2-methyl-cyclopentyl group, 3-methyl-cyclopentyl group, 1-ethyl-cyclobutyl group, 2-ethyl-cyclobutyl group, 3-ethyl-cyclobutyl group, 1,2-dimethyl-cyclobutyl group, 1, -Dimethyl-cyclobutyl group, 2,2-dimethyl-cyclobutyl group, 2,3-dimethyl-cyclobutyl group, 2,4-dimethyl-cyclobutyl group, 3,3-dimethyl-cyclobutyl group, 1-n
- aryl group examples include aryl groups having 6 to 20 carbon atoms, such as a phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl group, p-chlorophenyl group, o-fluorophenyl group, p-mercaptophenyl group, o-methoxyphenyl group, p-methoxyphenyl group, p-aminophenyl group, p-cyanophenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group O-biphenylyl group, m-biphenylyl group, p-biphenylyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanth
- 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.
- one or more hydrogen atoms are halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- a substituted alkyl group or an aryl group is mentioned.
- Examples of the organic group having an epoxy group include a glycidoxymethyl group, a glycidoxyethyl group, a glycidoxypropyl group, a glycidoxybutyl group, and an epoxycyclohexyl group.
- Examples of the organic group having an acryloyl group include an acryloylmethyl group, an acryloylethyl group, and an acryloylpropyl group.
- Examples of the organic group having a methacryloyl group include a methacryloylmethyl group, a methacryloylethyl group, and a methacryloylpropyl group.
- Examples of the organic group having a mercapto group include an ethyl mercapto group, a butyl mercapto group, a hexyl mercapto group, and an octyl mercapto group.
- Examples of the organic group having an amino group include an aminomethyl group, an aminoethyl group, and an aminopropyl group.
- Examples of the organic group having a cyano group include a cyanoethyl group and a cyanopropyl group.
- Examples of the organic group having a sulfonyl group include a methylsulfonyl group, an allylsulfonyl group, and a phenylsulfonyl group.
- alkoxy group examples include an alkoxy group having 1 to 30 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, for example, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, and an n-butoxy group.
- acyloxy group examples include an acyloxy group having 1 to 30 carbon atoms or, for example, 1 to 10 carbon atoms, such as a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, and an i-propyl.
- halogen atom examples include a fluorine atom, a chlorine group, a bromine atom, and an iodine atom.
- the compounds represented by formula (1) when R 1 represents an alkoxy group, R 1 is be the same alkoxy group may be a different alkoxy group. Further, when R 1 represents an acyloxy group or a halogen atom, R 1 may be the same acyloxy group or halogen group, or may be a different acyloxy group or halogen group.
- Examples of the compound represented by the formula (1) (hydrolyzable titanium compound) include tetramethoxy titanium, tetraethoxy titanium, tetraisopropoxy titanium, tetranormal butoxy titanium, tetraisobutoxy titanium, tetra-2-ethylhexoxy.
- Titanium tetrakis (methoxypropoxy) titanium, tetraphenoxy titanium, tetrabenzyloxy titanium, tetraphenylethoxy titanium, tetraphenoxyethoxy titanium, tetranaphthyloxy titanium, tetra-2-ethylhexoxy titanium, monoethoxytriisopropoxy titanium, Diisopropoxy diisobutoxy titanium, allyloxy (polyethyleneoxy) tris isopropoxy titanium, titanium chloride triisopropoxide, titanium dichloride dietoxide, t Alkoxy titanium such as nitro 2-ethylhexoxide, titanium iodotriisopropoxide, titanium tetramethoxypropoxide, titanium tetramethylphenoxide, titanium n-nonyloxide, titanium tetrastearyl oxide, titanium triisostearoyl monoisopropoxide Is mentioned.
- acyloxy such as tetramethylcarbonyloxytitanium, tetraethylcarbonyloxytitanium, tetra n-propylcarbonyloxytitanium, tetra i-propylcarbonyloxytitanium, methylcarbonyloxytriethylcarbonyloxytitanium, diethylcarbonyloxydi-i-propylcarbonyloxytitanium, etc.
- Titanium is mentioned.
- titanium halides such as titanium tetrafluoride, titanium tetrachloride, titanium tetrabromide, titanium tetraiodide, are mentioned.
- Examples of the compound (hydrolyzable titanium compound) represented by the formula (1) include hydrolyzable alkylalkoxytitanium, such as methyl titanium tris isopropoxide, ethyl titanium tris isopropoxide, methyl titanium trisbu. Toxides and the like can be mentioned.
- the hydrolyzable titanium dimer used in the present invention is a dimerization of alkoxy titanium, titanium halide, and acyloxy titanium with a Ti—O—Ti bond, and (R 1 ) 3 —Ti—O—Ti. -(R 1 ) 3 structure.
- Examples thereof include titanium butoxide dimer, titanium isobutoxide dimer, titanium propoxide dimer, and titanium isopropoxide dimer.
- titanium compound (A) a titanium compound selected from the group consisting of a compound represented by the formula (1) and a titanium chelate compound can be preferably used. And the titanium compound (A) can use preferably the titanium compound chosen from the group which consists of a compound represented by Formula (1).
- Silicon compound (B) represented by formula (2) used in the present invention [hereinafter also referred to as hydrolyzable silane compound (B).
- R 2 represents a nitrogen atom-containing ring group or an organic group containing the same, a condensed aromatic ring group or an organic group containing the same, a protected phenolic hydroxy group or an organic group containing the same, or a bisaryl group or the same.
- R 3 represents an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkenyl group, or an epoxy group
- R 4 represents an alkoxy group, an acyloxy group, or a halogen atom.
- a ′ represents an integer of 1
- b represents an integer of 0 or 1
- (a ′ + b) represents an integer of 1 or 2.
- the alkoxy group, acyloxy group, and halogen atom can be exemplified above.
- Examples of the nitrogen atom-containing cyclic group or the organic group containing the same include an organic group represented by the formula (4) and bonded to a silicon atom through a Si—C bond.
- R 7 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, an alkenyl group, an epoxy group, a sulfonyl group, or an organic group containing them
- R 8 represents 1 to 10 carbon atoms. Represents an alkylene group, a hydroxyalkylene group, a sulfide bond, an ether bond, an ester bond, or a combination thereof.
- X 1 represents Formula (5), Formula (6), or Formula (7).
- R 9 to R 13 are each independently a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms, an alkenyl group, an epoxy group, a sulfonyl group, Or the organic group containing them is represented.
- Examples of the nitrogen atom-containing cyclic group or the organic group containing the nitrogen atom include an imidazole group or an organic group containing an imidazole group.
- examples of the condensed aromatic ring group or the organic group containing the same include a naphthyl group and an anthryl group. Out-of-band absorption can be enhanced by using a condensed aromatic ring group.
- examples of the protected phenolic hydroxy group or the organic group containing the same include an alkoxyalkyl-substituted aryl group and an alkoxyalkoxyalkyl-substituted aryl group. By using a protected phenolic hydroxy group, the acidity is improved and the resist profile can be improved.
- a bisphenyl group can be mentioned as said bisaryl group or the organic group containing it.
- organic group having a cyano group, the organic group having a cyano group, and the organic group having a sulfonyl group include those described above.
- silicon compound (B) [hydrolyzable silane compound (B)] represented by the formula (2) can be listed below.
- Silicon compound (C) represented by formula (3) used in the present invention [hereinafter also referred to as hydrolyzable silane compound (C).
- R 5 is an alkyl group, aryl group, halogenated alkyl group, halogenated aryl group, alkenyl group, or epoxy group, acryloyl group, methacryloyl group, mercapto group, amino group, sulfonyl group, sulfide bond, ether bond, An organic group having an ester bond, a sulfonamide group, or a cyano group and bonded to a silicon atom by a Si—C bond.
- R 6 represents an alkoxy group, an acyloxy group, or a halogen atom
- a ′′ represents an integer of 0 to 3.
- these organic groups include those described above.
- the sulfonamido group include a phenylsulfonamido group and a methylsulfonamido group.
- Examples of the compound [hydrolyzable silane compound (C)] represented by the formula (3) include tetramethoxysilane, tetrachlorosilane, tetraacetoxysilane, tetraethoxysilane, tetra n-propoxysilane, tetraisopropoxysilane, Tetra n-butoxysilane, tetraacetoxysilane, methyltrimethoxysilane, methyltrichlorosilane, methyltriacetoxysilane, methyltripropoxysilane, methyltriacetoxysilane, methyltributoxysilane, methyltripropoxysilane, methyltriamyloxysilane , Methyltriphenoxysilane, methyltribenzyloxysilane, methyltriphenethyloxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysi
- hydrolysis-condensation product (polymer, copolymer) used in the present invention can be exemplified as follows.
- a method of obtaining a hydrolysis condensate of a mixture of a titanium compound (A) and a silicon compound (B) the compound represented by the above formula (1), a titanium chelate compound, and a hydrolyzable titanium dimer
- a hydrolysis condensate of a titanium compound (A) selected from the group consisting of a compound represented by (1), a titanium chelate compound, and a hydrolyzable titanium dimer, and a salt represented by the above formula (2) A method of mixing a hydrolyzed condensate of
- the above-mentioned hydrolysis condensate is a polymer or copolymer, and can be obtained as a condensate having a weight average molecular weight of 300 to 1000000, 300 to 100,000, or 300 to 20000. These molecular weights are molecular weights obtained in terms of polystyrene by GPC analysis.
- the GPC measurement conditions are, for example, a GPC apparatus (trade name HLC-8220 GPC, manufactured by Tosoh Corporation), a GPC column (trade names Shodex KF803L, KF802, KF801, Showa Denko Co., Ltd.), a column temperature of 40 ° C., and an eluent (elution)
- the solvent can be performed using tetrahydrofuran, the flow rate (flow rate) is 1.0 mL / min, and the standard sample is polystyrene (manufactured by Showa Denko KK).
- the hydrolysis of the alkoxysilyl group, the acyloxysilyl group, or the halogenated silyl group is performed in an amount of 0.5 to 100 mol, preferably 1 to 1 mol per mol of the hydrolyzable group. 10 moles of water are used. Further, 0.001 to 10 mol, preferably 0.001 to 1 mol of hydrolysis catalyst can be used per mol of the hydrolyzable group.
- the reaction temperature during the hydrolysis and condensation is usually 20 to 120 ° C. Hydrolysis may be performed completely or partially. That is, a hydrolyzate or a monomer may remain in the hydrolysis condensate.
- a catalyst can be used in the hydrolysis and condensation. Examples of the hydrolysis catalyst include metal chelate compounds, organic acids, inorganic acids, organic bases, and inorganic bases.
- Examples of the metal chelate compound as the hydrolysis catalyst include triethoxy mono (acetylacetonato) zirconium, tri-n-propoxy mono (acetylacetonato) zirconium, tri-i-propoxymono (acetylacetonato) zirconium, Tri-n-butoxy mono (acetylacetonato) zirconium, tri-sec-butoxy mono (acetylacetonato) zirconium, tri-t-butoxymono (acetylacetonato) zirconium, diethoxybis (acetylacetonato) Zirconium, di-n-propoxy bis (acetylacetonato) zirconium, di-i-propoxy bis (acetylacetonato) zirconium, di-n-butoxy bis (acetylacetonato) zirconium, -Sec-butoxy bis (acetylacetonato) zirconium
- organic acid as the hydrolysis catalyst examples include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, Sebacic acid, gallic acid, butyric acid, meritic acid, arachidonic acid, mikimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linolenic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfone Examples include acid, benzenesulfonic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid
- Examples of the inorganic acid as the hydrolysis catalyst include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
- organic base as the hydrolysis catalyst examples include pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, trimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyldiethanolamine, triethanolamine, diazabicyclooctane, Examples thereof include diazabicyclononane, diazabicycloundecene, and tetramethylammonium hydroxide.
- Examples of the inorganic base as the hydrolysis catalyst include ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide and the like.
- metal chelate compounds organic acids, and inorganic acids are preferable, and these may be used alone or in combination of two or more.
- organic solvent used for the hydrolysis examples include n-pentane, i-pentane, n-hexane, i-hexane, n-heptane, i-heptane, 2,2,4-trimethylpentane, n-octane, i -Aliphatic hydrocarbon solvents such as octane, cyclohexane, methylcyclohexane; benzene, toluene, xylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, i-propylbenzene, diethylbenzene, i-butylbenzene, triethylbenzene, Aromatic hydrocarbon solvents such as di-i-propylbenzene, n-amylnaphthalene, trimethylbenzene; methanol, ethanol, n-propano
- propylene glycol monomethyl ether propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono Propyl ether acetate is preferred.
- ketones such as acetone and non-alcohol polar solvents such as tetrahydrofuran are preferred, and the hydrolyzable silane compound (B) represented by the formula (2) (hydrolyzing group in the molecule of the silane compound during hydrolysis) Is preferably used as a raw material.
- the hydrolyzable silane compound (B) represented by the formula (2) hydrolyzing group in the molecule of the silane compound during hydrolysis
- acetone solvent is prone to hydrolysis and condensation so that gelation tends to occur.
- Hydrolysis condensation obtained by hydrolyzing and condensing hydrolyzable titanium, hydrolyzable silane compound (B) and hydrolyzable silane compound (C) with or without a catalyst in a solvent
- the product polymer, copolymer
- the product can be simultaneously removed by distillation under reduced pressure, etc., by-product alcohol, hydrolysis catalyst used in the reaction, and water.
- the acid or base catalyst used for hydrolysis can be removed by neutralization or ion exchange.
- an acid (organic acid), salt, water, alcohol, or those combinations can be added for stabilization.
- organic acid examples include oxalic acid, malonic acid, methylmalonic acid, succinic acid, maleic acid, malic acid, tartaric acid, phthalic acid, citric acid, glutaric acid, citric acid, lactic acid, and salicylic acid.
- oxalic acid maleic acid, acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, acrylic acid, methacrylic acid, crotonic acid, vinylacetic acid, hexenoic acid, fumaric acid, phenylacetic acid, phenylpropion Acid, triphenylacetic acid, cinnamic acid, benzoic acid, trimellitic acid, pyromellitic acid and the like are preferable.
- the organic acid to be added is 0.5 to 5.0 parts by mass with respect to 100 parts by mass of the condensate (polytitanoxane, polyorganosiloxane, copolymer or combination thereof). Moreover, pure water, ultrapure water, ion exchange water, etc. can be used for the water to add, The addition amount can be 1 thru
- the thin film forming composition used in the lithography process of the present invention may contain a ⁇ -diketone and / or a ⁇ -ketoester.
- ⁇ -diketone and / or ⁇ -ketoester can be used as a part of the solvent shown below.
- Examples of ⁇ diketone and / or ⁇ ketoester include acetylacetone, methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, i-propyl acetoacetate, n-butyl acetoacetate, i-butyl acetoacetate, sec-acetoacetate Butyl, tert-butyl acetoacetate, 2,4-hexanedione, 2,4-pentanedione, 2,4-heptanedione, 3,5-heptanedione, 2,4-octanedione, 3,5-octanedione, Examples include 2,4-nonanedione, 3,5-nonanedione, and 5-methyl-2,4-hexanedione.
- acetylacetone and ethyl acetoacetate are preferred. These components can be used alone or in admixture of two or more. This ⁇ -diketone and / or ⁇ -ketoester is used in an amount of 1 to 2000 parts by mass, or 10 to 500 parts by mass with respect to 100 parts by mass of the condensate (polytitanoxane, polyorganosiloxane, copolymer or combination thereof). Can do.
- a complex compound that forms a complex with titanium or silicon can be added.
- An example of such a complex compound is allyl alcohol.
- bisphenol S or a bisphenol S derivative can be added as an additive.
- the bisphenol S or the bisphenol S derivative is 0.01 to 20 parts by mass, or 0.01 to 10 parts by mass with respect to 100 parts by mass of the condensate (polytitanoxane, polyorganosiloxane, copolymer, or a combination thereof). Or 0.01 to 5 parts by mass.
- Preferred bisphenol S or bisphenol S derivatives are exemplified below.
- the thin film forming composition of the present invention may contain a salt.
- the salt serves as a curing catalyst when a coating film containing a condensate (polytitanoxane, polyorganosiloxane, copolymer, or a combination thereof) is heated and cured.
- a condensate polytitanoxane, polyorganosiloxane, copolymer, or a combination thereof
- ammonium salts, phosphines, phosphonium salts, and sulfonium salts can be used.
- ammonium salt As the ammonium salt, the formula (E-1): (Wherein m is an integer of 2 to 11, n is an integer of 2 to 3, R 14 is an alkyl group or an aryl group, and Y ⁇ is an anion.)
- the formula (E-7) (However, R 24 , R 25 , R 26 and R 27 each independently represents an alkyl group or an aryl group, P represents a phosphorus atom, Y ⁇ represents an anion, and R 24 , R 25 , R 26) , And R 27 are each bonded to a phosphorus atom by a CP bond.).
- R 28 , R 29 and R 30 are each independently an alkyl group or an aryl group, S is a sulfur atom, Y ⁇ is an anion, and R 28 , R 29 and R 30 are each And a tertiary sulfonium salt represented by the following formula:
- the compound represented by the above formula (E-1) is a quaternary ammonium salt derived from an amine, m represents an integer of 2 to 11, and n represents an integer of 2 to 3.
- R 14 of this quaternary ammonium salt represents an alkyl group or aryl group having 1 to 18 carbon atoms, preferably 2 to 10 carbon atoms, such as a linear alkyl group such as an ethyl group, a propyl group or a butyl group, benzyl Group, cyclohexyl group, cyclohexylmethyl group, dicyclopentadienyl group and the like.
- anion (Y ⁇ ) examples include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). And acid groups such as alcoholate (—O ⁇ ).
- the compound represented by the above formula (E-2) is a quaternary ammonium salt represented by R 15 R 16 R 17 R 18 N + Y ⁇ .
- R 15 , R 16 , R 17 and R 18 are each independently an alkyl group or aryl group having 1 to 18 carbon atoms, or a silane bonded to a silicon atom by a Si—C bond.
- the anion (Y ⁇ ) include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ).
- This quaternary ammonium salt can be obtained as a commercial product, for example, tetramethylammonium acetate, tetrabutylammonium acetate, triethylbenzylammonium chloride, triethylbenzylammonium bromide, trioctylmethylammonium chloride, tributylbenzyl chloride. Examples include ammonium and trimethylbenzylammonium chloride.
- the compound represented by the above formula (E-3) is a quaternary ammonium salt derived from 1-substituted imidazole, and R 19 and R 20 are each independently an alkyl group having 1 to 18 carbon atoms. Alternatively, it represents an aryl group, and the total number of carbon atoms of R 19 and R 20 is preferably 7 or more.
- R 19 can be exemplified by methyl group, ethyl group, propyl group, phenyl group and benzyl group
- R 20 can be exemplified by benzyl group, octyl group and octadecyl group.
- Y ⁇ examples include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). And acid groups such as alcoholate (—O ⁇ ).
- This compound can be obtained as a commercial product.
- imidazole compounds such as 1-methylimidazole and 1-benzylimidazole are reacted with alkyl halides and aryl halides such as benzyl bromide and methyl bromide. Can be manufactured.
- the compound represented by the above formula (E-4) is a quaternary ammonium salt derived from pyridine, and R 21 is an alkyl group having 1 to 18 carbon atoms, preferably 4 to 18 carbon atoms, or An aryl group, for example, a butyl group, an octyl group, a benzyl group, and a lauryl group.
- R 21 is an alkyl group having 1 to 18 carbon atoms, preferably 4 to 18 carbon atoms, or An aryl group, for example, a butyl group, an octyl group, a benzyl group, and a lauryl group.
- the anion (Y ⁇ ) include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ).
- This compound can also be obtained as a commercial product, or, for example, a reaction between pyridine and alkyl halide such as lauryl chloride, benzyl chloride, benzyl bromide, methyl bromide, octyl bromide, or aryl halide. Can be manufactured. Examples of this compound include N-laurylpyridinium chloride and N-benzylpyridinium bromide.
- the compound represented by the above formula (E-5) is a quaternary ammonium salt derived from a substituted pyridine represented by picoline or the like, and R 22 has 1 to 18 carbon atoms, preferably 4 to 18 carbon atoms.
- An alkyl group or an aryl group for example, a methyl group, an octyl group, a lauryl group, a benzyl group, and the like.
- R 23 represents an alkyl group having 1 to 18 carbon atoms or an aryl group. For example, in the case of quaternary ammonium derived from picoline, R 23 represents a methyl group.
- Y ⁇ examples include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). And acid groups such as alcoholate (—O ⁇ ).
- This compound can be obtained as a commercial product, or substituted pyridine such as picoline and alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride and benzyl bromide, or halogenated It can be produced by reacting aryl. Examples of this compound include N-benzylpicolinium chloride, N-benzylpicolinium bromide, N-lauryl picolinium chloride and the like.
- the compound represented by the above formula (E-6) is a tertiary ammonium salt derived from an amine, m represents an integer of 2 to 11, and n represents an integer of 2 to 3.
- the anion (Y ⁇ ) include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ).
- acid groups such as alcoholate (—O ⁇ ).
- This compound can be produced by reacting an amine with a weak acid such as carboxylic acid or phenol.
- the carboxylic acid include formic acid and acetic acid.
- the anion (Y ⁇ ) is (HCOO ⁇ ), and when acetic acid is used, the anion (Y ⁇ ) is (CH 3 COO). - ) When phenol is used, the anion (Y ⁇ ) is (C 6 H 5 O ⁇ ).
- the compound represented by the above formula (E-7) is a quaternary phosphonium salt having a structure represented by R 24 R 25 R 26 R 27 P + Y ⁇ .
- R 24 , R 25 , R 26 , and R 27 are each independently an alkyl or aryl group having 1 to 18 carbon atoms, or a silane compound bonded to a silicon atom through a Si—C bond.
- R 11 to R 14 three represent a phenyl group or a substituted phenyl group, and examples thereof include a phenyl group and a tolyl group, and the remaining one has 1 carbon atom.
- anion (Y ⁇ ) include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ).
- acid groups such as alcoholate (—O ⁇ ).
- This compound can be obtained as a commercial product, for example, a halogenated tetraalkylphosphonium such as tetra-n-butylphosphonium halide, tetra-n-propylphosphonium halide, or a trialkylbenzyl halide such as triethylbenzylphosphonium halide.
- a halogenated tetraalkylphosphonium such as tetra-n-butylphosphonium halide, tetra-n-propylphosphonium halide, or a trialkylbenzyl halide such as triethylbenzylphosphonium halide.
- Triphenylmonoalkylphosphonium halides such as phosphonium, triphenylmethylphosphonium halide, triphenylethylphosphonium halide, triphenylbenzylphosphonium halide, tetraphenylphosphonium halide, tritolylmonoarylphosphonium halide, or tritolyl monohalogenate Examples thereof include alkylphosphonium (wherein the halogen atom is a chlorine atom or a bromine atom).
- halogens such as triphenylmonoalkylphosphonium halides such as triphenylmethylphosphonium halide, triphenylethylphosphonium halide, triphenylmonoarylphosphonium halides such as triphenylbenzylphosphonium halide, and halogens such as tritolylmonophenylphosphonium halide.
- Preferred is a tolylyl monoarylphosphonium halide, or a tolyl monoalkylphosphonium halide such as a tolyl monomethylphosphonium halide (wherein the halogen atom is a chlorine atom or a bromine atom).
- the phosphines include methylphosphine, ethylphosphine, propylphosphine, isopropylphosphine, isobutylphosphine, phenylphosphine and other first phosphine, dimethylphosphine, diethylphosphine, diisopropylphosphine, diisoamylphosphine and diphenylphosphine And tertiary phosphines such as trimethylphosphine, triethylphosphine, triphenylphosphine, methyldiphenylphosphine, and dimethylphenylphosphine.
- the compound represented by the above formula (E-8) is a tertiary sulfonium salt having a structure represented by R 28 R 29 R 30 S + Y ⁇ .
- R 28 , R 29 , and R 30 are each independently an alkyl group or aryl group having 1 to 18 carbon atoms, or a silane compound bonded to a silicon atom by a Si—C bond.
- R 15 to R 17 three represent a phenyl group or a substituted phenyl group, and examples thereof include a phenyl group and a tolyl group, and the remaining one has 1 carbon atom.
- Y ⁇ examples include halogen ions such as chlorine ion (Cl ⁇ ), bromine ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). And acid groups such as alcoholate (—O ⁇ ).
- halogenated tetraalkylsulfonium such as tri-n-butylsulfonium halide and tri-n-propylsulfonium halide
- trialkylbenzyl halide such as diethylbenzylsulfonium halide.
- Halogenated diphenylmonoalkylsulfonium such as sulfonium, halogenated diphenylmethylsulfonium, halogenated diphenylethylsulfonium, triphenylsulfonium halide (the halogen atom is a chlorine atom or bromine atom), tri-n-butylsulfonium carboxylate, tri-n -Tetraalkylphosphonium carboxylates such as propylsulfonium carboxylate and trialkyls such as diethylbenzylsulfonium carboxylate Emissions Jill sulfonium carboxylate, diphenylmethyl sulfonium carboxylate, diphenyl monoalkyl sulfonium carboxylates such as diphenylethyl sulfonium carboxylate include triphenylsulfonium carboxylate. Particularly, triphenylsulfonium halide and
- the salt is 0.01 to 10 parts by mass, or 0.01 to 5 parts by mass, or 0.01 to 100 parts by mass with respect to 100 parts by mass of the condensate (polytitanoxane, polyorganosiloxane, copolymer, or a combination thereof). 3 parts by mass.
- the thin film-forming composition used in the lithography process of the present invention can contain an organic polymer compound, a photoacid generator, a surfactant, and the like as necessary in addition to the above components.
- the dry etching rate (thickness reduction per unit time), attenuation coefficient, refractive index, etc. of the thin film formed from the thin film forming composition used in the lithography process of the present invention are adjusted. Can do.
- an organic polymer compound A various organic polymer can be used. Polycondensation polymers and addition polymerization polymers can be used. Addition polymerization polymers and condensation polymerization polymers such as polyester, polystyrene, polyimide, acrylic polymer, methacrylic polymer, polyvinyl ether, phenol novolak, naphthol novolak, polyether, polyamide, and polycarbonate can be used.
- organic polymers having an aromatic ring structure such as a benzene ring, a naphthalene ring, an anthracene ring, a triazine ring, a quinoline ring, and a quinoxaline ring that function as a light absorption site are preferably used.
- organic polymer compounds include addition polymerizable monomers such as benzyl acrylate, benzyl methacrylate, phenyl acrylate, naphthyl acrylate, anthryl methacrylate, anthryl methyl methacrylate, styrene, hydroxystyrene, benzyl vinyl ether, and N-phenylmaleimide.
- addition-polymerized polymers containing as a structural unit, and polycondensation polymers such as phenol novolac and naphthol novolak.
- the polymer compound When an addition polymerization polymer is used as the organic polymer compound, the polymer compound may be a homopolymer or a copolymer.
- An addition polymerizable monomer is used for the production of the addition polymerization polymer.
- examples of such addition polymerizable monomers include acrylic acid, methacrylic acid, acrylic ester compounds, methacrylic ester compounds, acrylamide compounds, methacrylamide compounds, vinyl compounds, styrene compounds, maleimide compounds, maleic anhydride, acrylonitrile and the like. It is done.
- acrylate compound examples include methyl acrylate, ethyl acrylate, normal hexyl acrylate, isopropyl acrylate, cyclohexyl acrylate, benzyl acrylate, phenyl acrylate, anthryl methyl acrylate, 2-hydroxyethyl acrylate, and 3-chloro-2-hydroxypropyl acrylate.
- methacrylic acid ester compounds examples include methyl methacrylate, ethyl methacrylate, normal hexyl methacrylate, isopropyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, phenyl methacrylate, anthryl methyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,2 , 2-trifluoroethyl methacrylate, 2,2,2-trichloroethyl methacrylate, 2-bromoethyl methacrylate, 4-hydroxybutyl methacrylate, 2-methoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 2-methyl-2-adamantyl methacrylate, 5-Methacryloyloxy-6-hydroxynorbornene-2-cal Kishirikku 6- lactone, 3-methacryloxypropyl triethoxysilane, g
- acrylamide compound examples include acrylamide, N-methyl acrylamide, N-ethyl acrylamide, N-benzyl acrylamide, N-phenyl acrylamide, N, N-dimethyl acrylamide and N-anthryl acrylamide.
- methacrylamide compounds include methacrylamide, N-methyl methacrylamide, N-ethyl methacrylamide, N-benzyl methacrylamide, N-phenyl methacrylamide, N, N-dimethyl methacrylamide, N-anthryl methacrylamide, and the like. Can be mentioned.
- vinyl compound examples include vinyl alcohol, 2-hydroxyethyl vinyl ether, methyl vinyl ether, ethyl vinyl ether, benzyl vinyl ether, vinyl acetic acid, vinyl trimethoxysilane, 2-chloroethyl vinyl ether, 2-methoxyethyl vinyl ether, vinyl naphthalene and vinyl anthracene. Is mentioned.
- styrene compound examples include styrene, hydroxystyrene, chlorostyrene, bromostyrene, methoxystyrene, cyanostyrene, and acetylstyrene.
- maleimide compounds include maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and N-hydroxyethylmaleimide.
- examples of such an organic polymer include a polycondensation polymer of a glycol compound and a dicarboxylic acid compound.
- examples of the glycol compound include diethylene glycol, hexamethylene glycol, butylene glycol and the like.
- examples of the dicarboxylic acid compound include succinic acid, adipic acid, terephthalic acid, and maleic anhydride.
- examples of the polycondensation polymer include polyesters such as polypyromellitimide, poly (p-phenylene terephthalamide), polybutylene terephthalate, polyethylene terephthalate, polyamide, and polyimide.
- the hydroxy group can form a crosslinking reaction with the polyorganosiloxane.
- the organic polymer compound a polymer compound having a weight average molecular weight of, for example, 1,000 to 1,000,000, 3,000 to 300,000, 5,000 to 200,000, or 10,000 to 100,000 can be used. Only one organic polymer compound can be used, or two or more organic polymer compounds can be used in combination.
- the proportion thereof is 1 to 200 parts by mass, or 5 to 100 parts by mass with respect to 100 parts by mass of the condensate (polytitanoxane, polyorganosiloxane, copolymer, or a combination thereof). Part, or 10 to 50 parts by mass, or 20 to 30 parts by mass.
- the thin film forming composition of the present invention may contain an acid generator.
- the acid generator include a thermal acid generator and a photoacid generator.
- the photoacid generator generates an acid when the resist is exposed. Therefore, the acidity of the lower layer film can be adjusted. This is a method for matching the acidity of the lower layer film with the acidity of the upper layer resist. Further, the pattern shape of the resist formed in the upper layer can be adjusted by adjusting the acidity of the lower layer film.
- the photoacid generator contained in the thin film forming composition of the present invention include onium salt compounds, sulfonimide compounds, and disulfonyldiazomethane compounds.
- onium salt compounds examples include diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoronormalbutanesulfonate, diphenyliodonium perfluoronormaloctanesulfonate, diphenyliodonium camphorsulfonate, bis (4-tert-butylphenyl) iodonium.
- Iodonium salt compounds such as camphorsulfonate and bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, and triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoronormal butanesulfonate, triphenylsulfonium camphorsulfonate, and triphenyl Sulfonium salt compounds such as sulfonium trifluoromethanesulfonate, and the like.
- sulfonimide compound examples include N- (trifluoromethanesulfonyloxy) succinimide, N- (nonafluoronormalbutanesulfonyloxy) succinimide, N- (camphorsulfonyloxy) succinimide, and N- (trifluoromethanesulfonyloxy) naphthalimide. Is mentioned.
- disulfonyldiazomethane compound examples include bis (trifluoromethylsulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, bis (phenylsulfonyl) diazomethane, bis (p-toluenesulfonyl) diazomethane, and bis (2,4-dimethylbenzene).
- Sulfonyl) diazomethane methylsulfonyl-p-toluenesulfonyldiazomethane, and the like.
- the said photo-acid generator can use only 1 type, or can be used in combination of 2 or more type.
- the ratio is 0.01-5 mass parts with respect to 100 mass parts of condensates (poly titanoxane, polyorganosiloxane, a copolymer, or those combinations), or 0.00. 1 to 3 parts by mass, or 0.5 to 1 part by mass.
- the surfactant is effective for suppressing the occurrence of pinholes and installations when the thin film forming composition of the present invention is applied to a substrate.
- the surfactant contained in the thin film forming composition of the present invention for example, polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, Polyoxyethylene alkyl allyl ethers such as polyoxyethylene octylphenol ether and polyoxyethylene nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monoole Sorbitan trioleate, sorbitan fatty acid esters such as sorbitan tristearate, polyoxyethylene sorbitan mono Nonionic surfactants and products such as polyoxyethylene sorbitan fatty acid esters such as ur
- surfactants may be used alone or in combination of two or more.
- the ratio is 0.0001 to 5 parts by mass, or 0.001 to 100 parts by mass with respect to 100 parts by mass of the condensate (polytitanoxane, polyorganosiloxane, copolymer, or a combination thereof). 3 parts by mass, or 0.01 to 0.5 parts by mass.
- a rheology adjusting agent, an adhesion aid and the like can be added to the thin film forming composition of the present invention.
- the rheology modifier is effective in improving the fluidity of the thin film forming composition.
- Adhesion aids are effective in improving the adhesion between the semiconductor substrate or resist and the thin film.
- any solvent can be used without particular limitation as long as it is a solvent capable of dissolving the solid content.
- solvents include methanol, ethanol, propanol, isopropanol, butanol, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether.
- the thin film forming composition of the present invention comprises a resist underlayer film forming composition such as a photoresist, a resist underlayer film forming composition such as an EUV resist, an EUV resist upper layer film forming composition, a reverse material forming composition, and a solvent developing resist. It can be used as an underlayer film forming composition.
- a resist underlayer film forming composition such as a photoresist
- a resist underlayer film forming composition such as an EUV resist
- EUV resist upper layer film forming composition such as an EUV resist upper layer film forming composition
- a reverse material forming composition such as an EUV resist upper layer film forming composition
- Substrates used in the manufacture of semiconductor devices eg, silicon wafer substrates, silicon / silicon dioxide coated substrates, silicon nitride substrates, glass substrates, ITO substrates, polyimide substrates, and low dielectric constant (low-k material) coated substrates) Etc.
- the thin film forming composition (resist underlayer film forming composition) of the present invention by an appropriate application method such as a spinner or a coater, and then fired to form a thin film (resist underlayer film).
- the conditions for firing are appropriately selected from firing temperatures of 80 ° C. to 500 ° C., or 80 ° C. to 250 ° C., and firing times of 0.3 to 60 minutes.
- the baking temperature is 150 ° C.
- the film thickness of the formed thin film is, for example, 10 to 1000 nm, 20 to 500 nm, 50 to 300 nm, 100 to 200 nm, or 10 to 100 nm.
- a photoresist layer (film) is formed on the thin film (resist underlayer film).
- the formation of the photoresist layer can be performed by a well-known method, that is, by applying and baking a photoresist composition solution on the lower layer film.
- the film thickness of the photoresist layer is, for example, 50 to 10,000 nm, 100 to 2000 nm, 200 to 1000 nm, or 30 to 200 nm.
- the thin film (resist underlayer film) of the present invention is formed thereon, and a photoresist layer can be further coated thereon.
- the pattern width of the photoresist layer becomes narrow, and even when the photoresist layer is thinly coated to prevent pattern collapse, the substrate can be processed by selecting an appropriate etching gas.
- the organic underlayer film can be processed using an oxygen-based gas that provides a sufficiently high etching rate as an etching gas, and the substrate is processed using a fluorine-based gas that provides a sufficiently high etching rate for the organic underlayer film as an etching gas. be able to.
- the photoresist formed on the thin film (resist underlayer film) of the present invention is not particularly limited as long as it is sensitive to light used for exposure. Either a negative photoresist or a positive photoresist can be used.
- a positive photoresist comprising a novolac resin and 1,2-naphthoquinonediazide sulfonic acid ester, a chemically amplified photoresist comprising a binder having a group that decomposes with an acid to increase the alkali dissolution rate and a photoacid generator, an acid
- a chemically amplified photoresist comprising a low-molecular compound that decomposes to increase the alkali dissolution rate of the photoresist, an alkali-soluble binder, and a photoacid generator, and a binder having a group that decomposes with an acid to increase the alkali dissolution rate
- Examples include trade name APEX-E manufactured by Shipley, trade name PAR710 manufactured by Sumitomo Chemical Co., Ltd., and trade name SEPR430 manufactured by Shin-Etsu Chemical Co., Ltd. Also, for example, Proc. SPIE, Vol. 3999, 330-334 (2000), Proc. SPIE, Vol. 3999, 357-364 (2000), Proc. SPIE, Vol. 3999, 365-374 (2000), and fluorine-containing polymer-based photoresists.
- a KrF excimer laser (wavelength 248 nm), an ArF excimer laser (wavelength 193 nm), an F2 excimer laser (wavelength 157 nm), or the like can be used.
- post-exposure bake can be performed as necessary.
- the post-exposure heating is performed under conditions appropriately selected from a heating temperature of 70 ° C. to 150 ° C. and a heating time of 0.3 to 10 minutes.
- a resist for electron beam lithography or an EUV resist can be used as the resist instead of the photoresist.
- the electron beam resist either a negative type or a positive type can be used.
- Chemically amplified resist comprising a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate, a low molecular weight compound that decomposes with an alkali-soluble binder, an acid generator and an acid to change the alkali dissolution rate of the resist
- a chemically amplified resist comprising a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate and a low molecular weight compound that decomposes with an acid to change the alkali dissolution rate of the resist,
- non-chemically amplified resists composed of a binder having a group that is decomposed by an electron beam to change the alkali dissolution rate and non-chemically amplified resists composed
- Developers include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, aqueous solutions of quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, ethanolamine, propylamine, An alkaline aqueous solution such as an aqueous amine solution such as ethylenediamine can be mentioned as an example. Further, a surfactant or the like can be added to these developers.
- the development conditions are appropriately selected from a temperature of 5 to 50 ° C. and a time of 10 to 600 seconds.
- the thin film (resist lower layer film) (intermediate layer) of the present invention is removed using the photoresist film (upper layer) pattern thus formed as a protective film.
- the organic underlayer film (lower layer) is removed using the patterned photoresist and the film made of the thin film (resist underlayer film) (intermediate layer) of the present invention as a protective film.
- the semiconductor substrate is processed using the patterned thin film (resist underlayer film) (intermediate layer) and organic underlayer film (lower layer) of the present invention as protective films.
- the thin film (resist underlayer film) (intermediate layer) of the present invention in the portion where the photoresist has been removed is removed by dry etching to expose the semiconductor substrate.
- dry etching of the thin film (resist underlayer film) of the present invention tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, carbon monoxide, Gases such as argon, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, nitrogen trifluoride and chlorine trifluoride, chlorine, trichloroborane and dichloroborane can be used.
- a photoresist composed of an organic substance is basically difficult to remove, whereas the thin film of the present invention (resist underlayer film) containing a large amount of silicon atoms is quickly removed using a halogen-based gas. Therefore, it is preferable to use a halogen-based gas for dry etching of the resist underlayer film. Thereby, a reduction in the film thickness of the photoresist accompanying dry etching of the thin film (resist underlayer film) can be suppressed. As a result, the photoresist can be used as a thin film. Dry etching of the resist underlayer film can also be performed with a fluorine-based gas.
- fluorine-based gas examples include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, and difluoromethane (CH 2 F 2 ).
- CF 4 tetrafluoromethane
- C 4 F 8 perfluorocyclobutane
- C 3 F 8 perfluoropropane
- CH 2 F 2 difluoromethane
- the dry etching of the titanium-silicon-containing thin film (resist underlayer film) of the present invention is preferably performed using a halogen-based gas.
- the halogen-based gas examples include hydrogen bromide (HBr) and chlorine (Cl).
- Etching selectivity with the resist can be obtained by mixing with fluorine-based gas such as 4 or CHF 3 or oxygen-based gas such as O 2 .
- the organic underlayer film is removed using the patterned photoresist and the film made of the thin film (resist underlayer film) of the present invention as a protective film.
- the organic underlayer film (underlayer) and the organic antireflection film are preferably formed by dry etching with an oxygen-based gas. This is because the thin film (resist underlayer film) of the present invention containing a large amount of silicon atoms is difficult to remove by dry etching with an oxygen-based gas.
- the semiconductor substrate is processed.
- the semiconductor substrate is preferably processed by dry etching with a fluorine-based gas.
- fluorine-based gas examples include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, and difluoromethane (CH 2 F 2 ). Can be mentioned.
- an organic antireflection film can be formed on the thin film (resist underlayer film) of the present invention before the formation of the photoresist layer (film).
- the antireflection film composition used there is not particularly limited, and any of those conventionally used in the lithography process can be selected and used. Further, the antireflection film can be formed by a commonly used method, for example, application and baking with a spinner or a coater.
- the semiconductor device manufacturing method of the present invention includes, as such a multilayer process, a step of forming an organic underlayer film on a semiconductor substrate, and a thin film forming composition (resist underlayer film forming composition) of the present invention is applied thereon.
- coated has an organic or inorganic antireflection film formed in the surface by CVD method etc. It is also possible to form the thin film (resist underlayer film) of the present invention on it.
- a thin film (resist underlayer film) formed from the thin film forming composition (resist underlayer film forming composition) of the present invention may have absorption of light depending on the wavelength of light used in the lithography process. . In such a case, it can function as an antireflection film having an effect of preventing reflected light from the substrate. Furthermore, the thin film (resist underlayer film) of the present invention is a layer for preventing the interaction between the substrate and the photoresist, the material used for the photoresist, or the adverse effect on the substrate of the substance generated upon exposure to the photoresist.
- a layer having a function of preventing diffusion, a layer having a function of preventing diffusion of a substance generated from a substrate upon heating and firing into an upper layer photoresist, and a barrier layer for reducing a poisoning effect of the photoresist layer by a semiconductor substrate dielectric layer Etc. can also be used.
- a thin film (resist underlayer film) formed from the thin film forming composition (resist underlayer film forming composition) of the present invention is applied to a substrate on which via holes used in a dual damascene process are formed, and the holes are filled without gaps. Can be used as an embedding material. Moreover, it can also be used as a planarizing material for planarizing the surface of an uneven semiconductor substrate.
- the thin film forming composition of the present invention is used as an EUV resist upper layer film forming composition or an EUV resist lower layer film forming composition will be described.
- the EUV resist applied to the lower layer of the EUV resist upper layer film in the present invention either a negative type or a positive type can be used.
- Chemically amplified resist comprising a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate, a low molecular weight compound that decomposes with an alkali-soluble binder, an acid generator and an acid to change the alkali dissolution rate of the resist
- a chemically amplified resist comprising: a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate; and a chemically amplified resist comprising a low-molecular compound that decomposes with an acid to change the alkali dissolution rate of the resist,
- a non-chemically amplified resist composed of a binder having a group that is decomposed by EUV to change the alkali dissolution rate
- a non-chemically amplified resist composed of a binder having a portion that is cut by EUV to change the alkali dissolution rate.
- Inorganic alkalis such as sodium silicate, sodium metasilicate, aqueous ammonia, etc.
- primary amines such as ethylamine and n-propylamine
- secondary amines
- aqueous solution Door can be. Furthermore, an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- an alcohol such as isopropyl alcohol or a nonionic surfactant
- preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
- the method of manufacturing a semiconductor device of the present invention includes a step of forming an EUV resist film on a substrate having a film to be processed on which a transfer pattern is to be formed, with or without using an EUV resist underlayer film, and an EUV on the resist film.
- a step of applying and baking a resist upper layer film forming composition to form an EUV resist upper layer film a step of exposing a semiconductor substrate coated with the resist upper layer film and the resist film, and developing after exposure to develop the resist upper layer film and the resist film The process of removing.
- Exposure is performed by EUV (wavelength 13.5 nm).
- a semiconductor device to which the thin film forming composition (EUV resist upper layer film forming composition) of the present invention is applied is formed on a substrate in order of a film to be processed to transfer a pattern, a resist film, and a thin film (EUV resist upper layer film). It has the structure made.
- This thin film (upper layer film of EUV resist) can reduce the adverse effect exerted by the underlying substrate and EUV, thereby forming a straight resist pattern with a good margin and obtaining a sufficient margin for the EUV irradiation amount.
- the thin film (EUV resist upper layer film) of the present invention has a large wet etching rate equivalent to that of the resist film formed in the lower layer, and easily transfers the resist pattern to the base film to be processed by the wet etching process. be able to.
- the lower layer reflection of the EUV resist that can prevent reflection from undesirable exposure light, for example, the above-described UV or DUV substrate or interface, without intermixing with the EUV resist.
- the thin film forming composition (EUV resist underlayer film forming composition) of the present invention can be used. Reflection can be efficiently prevented in the lower layer of the EUV resist.
- the process can be performed in the same manner as the photoresist underlayer film.
- the thin film by the thin film formation composition of this invention can be used as a reverse material. That is, a step of forming a resist pattern on a substrate, a step of applying and baking the thin film forming composition of the present invention thereon to form a thin film, a step of etching the thin film to expose the resist surface, and etching the resist pattern And a method of manufacturing a semiconductor device including a step of inverting the pattern.
- the thin film formation composition of the present invention is apply
- an organic underlayer film can be formed on the substrate, and the thin film can be formed thereon.
- the photoresist formed on the thin film (resist underlayer film) of the present invention is not particularly limited as long as it is sensitive to light used for exposure such as ArF light. Either a negative photoresist or a positive photoresist can be used. Any photoresist that can be developed with an organic solvent after exposure can be used. The above conditions can be applied as conditions for firing. Next, for example, the photoresist layer (film) is formed on the thin film.
- a resist for EUV lithography and a resist for electron beam lithography can be used instead of the photoresist.
- a resist for EUV lithography and a resist for electron beam lithography either a negative type or a positive type can be used.
- the above conditions can be used as exposure conditions. Any resist that can be developed with an organic solvent after exposure can be used.
- Examples of the developer include methyl acetate, butyl acetate, ethyl acetate, isopropyl acetate, amyl acetate, isoamyl acetate, ethyl methoxyacetate, ethyl ethoxy acetate, 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 monopropyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monophenyl ether acetate, diethylene glycol monobutyl ether acetate, die Lenglycol monoethyl ether acetate, 2-methoxybutyl acetate, 3-methoxy
- the developer butyl acetate, 2-heptanone or the like can be preferably used. Further, a surfactant or the like can be added to these developers.
- the development conditions are appropriately selected from a temperature of 5 to 50 ° C. and a time of 10 to 600 seconds.
- the thin film (intermediate layer) of the present invention is removed using the photoresist film (upper layer) pattern thus formed as a protective film.
- the organic underlayer film (lower layer) is removed using the patterned photoresist and the film made of the thin film (intermediate layer) of the present invention as a protective film.
- the semiconductor substrate is processed using the patterned thin film (intermediate layer) and organic lower layer film (lower layer) of the present invention as a protective film.
- the thin film (intermediate layer) of the present invention in the portion where the photoresist has been removed is removed by dry etching to expose the semiconductor substrate.
- dry etching of the thin film of the present invention tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, carbon monoxide, argon, oxygen, nitrogen Gases such as sulfur hexafluoride, difluoromethane, nitrogen trifluoride and chlorine trifluoride, chlorine, trichloroborane and dichloroborane can be used.
- a photoresist composed of an organic substance is basically difficult to remove, whereas the thin film of the present invention containing a large amount of silicon atoms is quickly removed with a halogen-based gas.
- a halogen-based gas for dry etching of the thin film of the present invention.
- the dry etching of the thin film of the present invention is preferably performed using a fluorine-based gas.
- fluorine-based gas examples include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), and perfluoropropane (C 3 F 8). ), Trifluoromethane, and difluoromethane (CH 2 F 2 ).
- the organic underlayer film is removed using the patterned photoresist and the film made of the thin film of the present invention as a protective film.
- the organic underlayer film (underlayer) is preferably formed by dry etching with an oxygen-based gas. This is because the thin film of the present invention containing a large amount of silicon atoms is difficult to remove by dry etching with an oxygen-based gas.
- the semiconductor substrate is processed.
- the semiconductor substrate is preferably processed by dry etching with a fluorine-based gas.
- fluorine-based gas examples include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, and difluoromethane (CH 2 F 2 ). Can be mentioned.
- an organic antireflection film can be formed on the upper layer of the thin film of the present invention before the formation of the photoresist layer (film).
- the antireflection film composition used there is not particularly limited, and any of those conventionally used in the lithography process can be selected and used. Further, the antireflection film can be formed by a commonly used method, for example, application and baking with a spinner or a coater.
- the thin film of the present invention after forming an organic underlayer film on a substrate, the thin film of the present invention can be formed thereon, and a photoresist layer can be further coated thereon.
- the substrate can be processed by selecting an appropriate etching gas.
- an appropriate etching gas For example, it is possible to process the thin film of the present invention using a fluorine-based gas that provides a sufficiently high etching rate for photoresist as an etching gas, and an oxygen-based gas that provides a sufficiently high etching rate for the thin film of the present invention.
- the organic underlayer film using the etching gas as an etching gas
- Synthesis example 1 Tetraisobutoxytitanium 18.60 g (70 mol%), methyltriethoxysilane 3.48 g (25 mol%), 3- (triethoxysilylpropyl) diallyl isocyanurate 1.62 g (5 mol%), acetone 35.55 g, acetylacetone 35 .55 g was placed in a 300 mL flask, and 5.21 g of 0.01 mol / L hydrochloric acid was added dropwise to the mixed solution while stirring the mixed solution with a magnetic stirrer. After the addition, the flask was transferred to an oil bath adjusted to 85 ° C., and reacted for 240 minutes under heating and reflux.
- reaction solution is cooled to room temperature, 48.00 g of acetylacetone is added to the reaction solution, and ethanol, acetone, isobutanol, water, and hydrochloric acid as reaction byproducts are distilled off under reduced pressure, and concentrated to hydrolyzed condensate (polymer).
- An acetylacetone solution was obtained. Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-1), and the weight average molecular weight by GPC was Mw 700 in terms of polystyrene.
- Synthesis example 2 Tetraisobutoxy titanium 11.59 g (50 mol%), methyltriethoxysilane 4.49 g (37 mol%), 3- (triethoxysilylpropyl) diallyl isocyanurate 0.85 g (3 mol%), phenyltrimethoxysilane 1.35 g (10 mol%), 27.42 g of acetone and 27.42 g of acetylacetone were placed in a 300 mL flask, and 4.30 g of 0.01 mol / L hydrochloric acid was added dropwise to the mixed solution while stirring the mixed solution with a magnetic stirrer.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-2), and the weight average molecular weight by GPC was Mw 900 in terms of polystyrene.
- Synthesis example 3 Tetraisopropoxytitanium 17.85 g (70 mol%), methyltriethoxysilane 3.20 g (20 mol%), biphenyl-4-yltrimethoxysilane 2.40 g (10 mol%), acetone 35.26 g, acetylacetone 35.26 g Into a 300 mL flask, 5.98 g of 0.01 mol / L hydrochloric acid was added dropwise to the mixed solution while stirring the mixed solution with a magnetic stirrer. After the addition, the flask was transferred to an oil bath adjusted to 85 ° C., and reacted for 240 minutes under heating and reflux.
- reaction solution is cooled to room temperature, 48.00 g of acetylacetone is added to the reaction solution, and methanol and ethanol, acetone, isopropanol, water and hydrochloric acid as reaction by-products are distilled off under reduced pressure and concentrated to obtain a hydrolysis-condensation product ( Polymer)
- Acetylacetone solution was obtained.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-3), and the weight average molecular weight by GPC was Mw 800 in terms of polystyrene.
- Synthesis example 4 300 mL of 18.01 g (70 mol%) of tetraisopropoxytitanium, 3.23 g (20 mol%) of methyltriethoxysilane, 2.25 g (10 mol%) of 1-naphthyltrimethoxysilane, 35.24 g of acetone and 35.24 g of acetylacetone Into the flask, 6.04 g of 0.01 mol / L hydrochloric acid was added dropwise to the mixed solution while stirring the mixed solution with a magnetic stirrer. After the addition, the flask was transferred to an oil bath adjusted to 85 ° C., and reacted for 240 minutes under heating and reflux.
- reaction solution is cooled to room temperature, 46.00 g of acetylacetone is added to the reaction solution, and methanol and ethanol, acetone, isopropanol, water and hydrochloric acid as reaction byproducts are distilled off under reduced pressure, and concentrated to a hydrolysis-condensation product ( Polymer)
- Acetylacetone solution was obtained.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-4), and the weight average molecular weight by GPC was Mw 800 in terms of polystyrene.
- Synthesis example 5 17.63 g (70 mol%) of tetraisopropoxytitanium, 3.16 g (20 mol%) of methyltriethoxysilane, 2.73 g (10 mol%) of 6- (methoxymethoxy) -2- (trimethoxysilyl) naphthalene, acetone 35. 28 g and 35.28 g of acetylacetone were placed in a 300 mL flask, and 5.91 g of 0.01 mol / L hydrochloric acid was added dropwise to the mixed solution while stirring the mixed solution with a magnetic stirrer. After the addition, the flask was transferred to an oil bath adjusted to 85 ° C., and reacted for 240 minutes under heating and reflux.
- reaction solution is cooled to room temperature, 48.00 g of acetylacetone is added to the reaction solution, and methanol and ethanol, acetone, isopropanol, water and hydrochloric acid as reaction by-products are distilled off under reduced pressure and concentrated to obtain a hydrolysis-condensation product ( Polymer)
- Acetylacetone solution was obtained.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-5), and the weight average molecular weight by GPC was Mw 800 in terms of polystyrene.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-6), and the weight average molecular weight by GPC was Mw 800 in terms of polystyrene.
- Synthesis example 7 Tetraisobutoxytitanium 18.74 g (70 mol%), methyltriethoxysilane 3.46 g (24.7 mol%), 3- (triethoxysilylpropyl) dimethylisocyanurate 1.42 g (5 mol%), N- (3- (Triethoxysilylpropyl) -4,5-dihydroimidazole (0.065 g, 0.3 mol%), acetone (35.53 g), and acetylacetone (35.53 g) were placed in a 300 mL flask, and the mixed solution was stirred while stirring with a magnetic stirrer. 5.25 g of 10 mol / L hydrochloric acid was added dropwise to the mixed solution.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-7), and the weight average molecular weight by GPC was Mw 800 in terms of polystyrene.
- Synthesis example 8 Tetraisobutoxytitanium 15.60 g (60 mol%), tetraethoxysilane 1.91 g (10 mol%), methyltriethoxysilane 4.08 g (25 mol%), 3- (triethoxysilylpropyl) diallyl isocyanurate 1.89 g ( 5 mol%), 35.21 g of acetone, and 35.21 g of acetylacetone were placed in a 300 mL flask, and 6.10 g of 0.01 mol / L hydrochloric acid was added dropwise to the mixed solution while stirring the mixed solution with a magnetic stirrer.
- Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (8-8), and the weight average molecular weight by GPC was Mw1000 in terms of polystyrene.
- reaction solution is cooled to room temperature, 48.00 g of acetylacetone is added to the reaction solution, and ethanol, acetone, isopropanol, water and hydrochloric acid as reaction by-products are distilled off under reduced pressure and concentrated to hydrolyzed condensate (polymer).
- An acetylacetone solution was obtained.
- Acetylacetone and 4-methyl 2-pentanol were added, and the solvent ratio of acetylacetone / 4-methyl 2-pentanol 5/95 was adjusted to 8 mass percent in terms of solid residue at 140 ° C.
- the weight average molecular weight by GPC of the obtained polymer formula (8-1) was Mw 800 in terms of polystyrene.
- reaction solution is cooled to room temperature, 48.00 g of acetylacetone is added to the reaction solution, and ethanol, acetone, isobutanol, water, and hydrochloric acid as reaction byproducts are distilled off under reduced pressure, and concentrated to hydrolyzed condensate (polymer).
- An acetylacetone solution was obtained. Acetylacetone and 4-methyl 2-pentanol were added, and the solvent ratio of acetylacetone / 4-methyl 2-pentanol 5/95 was adjusted to 8 mass percent in terms of solid residue at 140 ° C.
- the weight average molecular weight by GPC of the obtained polymer formula (8-1) was Mw 700 in terms of polystyrene.
- reaction solution is cooled to room temperature, 46.00 g of propylene glycol monoethyl ether is added to the reaction solution, and methanol, ethanol, acetone, water and hydrochloric acid as reaction by-products are distilled off under reduced pressure and concentrated to hydrolytic condensation.
- a product (polymer) propylene glycol monoethyl ether solution was obtained. Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the obtained polymer corresponded to Formula (9-1), and the weight average molecular weight by GPC was Mw 1200 in terms of polystyrene.
- reaction solution is cooled to room temperature, 48.00 g of acetylacetone is added to the reaction solution, and methanol and ethanol, acetone, isobutanol, water and hydrochloric acid as reaction by-products are distilled off under reduced pressure, and concentrated to hydrolyzed condensate.
- a (polymer) acetylacetone solution was obtained. Acetylacetone and propylene glycol monoethyl ether were added, and the solvent ratio of acetylacetone / propylene glycol monoethyl ether 10/90 was adjusted to 15 mass percent in terms of solid residue at 140 ° C.
- the weight average molecular weight by GPC of the obtained polymer formula (9-2) was Mw1000 in terms of polystyrene.
- maleic acid is MA
- benzyltriethylammonium chloride is BTAC
- N- (3-triethoxysilylpropyl) -4,5-dihydroimidazole is IMIDTEOS
- triphenylsulfonium trifluoromethanesulfonate is TPS105
- monotriphenyls maleate Rufonium is TPSMA
- propylene glycol monomethyl ether acetate PGMEA
- propylene glycol monoethyl ether is PGEE
- propylene glycol monomethyl ether is PGME
- acetylacetone is AcAc
- 4-methyl 2-pentanol ie methyl isobutyl carbinol
- MIBC Abbreviated. Water used was ultrapure water. Each addition amount was shown in parts by mass.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, and a solution of an organic underlayer film forming composition used in a lithography process using a multilayer film Was prepared.
- the thin film forming compositions (resist underlayer film forming compositions) prepared in Examples 1 to 15, Examples 18 to 19, and Comparative Examples 1 and 2 were each applied onto a silicon wafer using a spinner. The film was heated on a hot plate at 240 ° C. for 1 minute to form a thin film (resist underlayer film) (film thickness 0.05 ⁇ m). These thin films (resist underlayer films) were analyzed using a spectroscopic ellipsometer (JA Woollam, VUV-VASE VU-302), and the refractive index (n value) and optical absorption at wavelengths 193, 200, and 248 nm. Coefficients (k value, also called attenuation coefficient) were measured.
- n value refractive index
- k value also called attenuation coefficient
- the etcher and etching gas used for the measurement of the dry etching rate are as follows.
- RIE-10NR Sudco
- O 2 The solutions of the thin film forming compositions (resist underlayer film forming compositions) prepared in Examples 1 to 15, Examples 18 to 19, and Comparative Examples 1 and 2 were applied onto a silicon wafer using a spinner. Heating was performed at 240 ° C. for 1 minute on a hot plate to form a thin film (resist underlayer film) of 0.05 ⁇ m. Similarly, a coating film was formed on a silicon wafer (film thickness: 0.20 ⁇ m) using the organic underlayer film forming composition using a spinner. The dry etching rate was measured using O 2 gas as an etching gas, and the dry etching rates of the thin films (resist underlayer films) of Examples 1 to 15 and Comparative Examples 1 and 2 were compared.
- the organic underlayer film (A layer) forming composition obtained above was applied onto a silicon wafer and baked on a hot plate at 240 ° C. for 60 seconds to obtain an organic underlayer film (A layer) having a thickness of 200 nm.
- the thin film forming composition [resist underlayer film (B) forming composition] obtained in Examples 1 to 15, Examples 18 to 19, and Comparative Examples 1 and 2 was applied, and 240 ° C. on a hot plate. was baked for 45 seconds to obtain a thin film [resist underlayer film (B layer)].
- the film thickness of the thin film [resist underlayer film (B layer)] was 25 nm.
- a commercially available photoresist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR855) was applied on each of the films using a spinner, and baked on a hot plate at 100 ° C. for 60 seconds to form a 120 nm thick photoresist film (D layer ) Was formed.
- Patterning of the resist was performed using an ArF exposure machine S-307E (wavelength: 193 nm, NA, ⁇ : 0.85, 0.93 / 0.85 (Dipole) immersion liquid: water) manufactured by NIKON.
- the target was exposed through a mask set so as to form a so-called line and space (dense line) in which the line width of the photoresist and the width between the lines were 0.065 ⁇ m after development.
- the film was baked on a hot plate at 105 ° C. for 60 seconds, cooled, and developed with an aqueous tetramethylammonium hydroxide solution (developer) having a concentration of 2.38% by mass in a single paddle process for 60 seconds.
- developer aqueous tetramethylammonium hydroxide solution
- the patterned wafer was etched with the following etching gas, and the thin film shape (resist underlayer film shape) of the present invention after etching was observed.
- the thin film (resist underlayer film) of the present invention was etched under the following conditions using CF 4 gas, and then O 2 / N 2 gas.
- the organic resist underlayer film was etched by the above.
- Table 2 shows a refractive index n1 at a wavelength of 193 nm, an optical absorption coefficient k1, a refractive index n2 at a wavelength of 220 nm, an optical absorption coefficient k2, and a wavelength of 248 nm.
- the refractive index n3, the optical absorption coefficient k3, and the pattern shape after etching are shown.
- the electron micrograph of the shape after the etching of Example 1 is shown in FIG. Moreover, the electron micrograph of the shape after the etching of the comparative example 1 was shown in FIG.
- the shoulder drop (rounding) in the pattern shape after the etching is a phenomenon in which the pattern shoulder drop occurs due to oxygen-based etching when the pattern is transferred to the organic underlayer film, and the pattern becomes round. The more rectangular the pattern, the better the pattern can be transferred.
- the thin film forming composition (resist underlayer film forming composition) solutions prepared in Examples 1 to 19 and Comparative Examples 1 and 2 were applied onto a silicon wafer using a spinner. Heating was performed at 240 ° C. for 1 minute on a hot plate to form a thin film (resist underlayer film) of 0.05 ⁇ m. Moreover, the organic underlayer film formation composition was formed on the silicon wafer using the spinner (film thickness 0.20 micrometer). Similarly, a resist was applied on a silicon wafer using a spinner. Heating was performed at 100 ° C. for 1 minute on a hot plate to form a resist film of 0.10 ⁇ m.
- the thin film (resist underlayer film) used in the present invention has a higher etching rate (speed ratio 1) when transferring the resist pattern to the thin film (resist underlayer film) of the present invention than the resist underlayer film of the comparative example. Can be transferred to.
- the organic underlayer film (A layer) formation composition obtained by the above formula (10-1) was applied on a silicon wafer, baked on a hot plate at 400 ° C. for 60 seconds, and a film thickness of 200 nm was obtained. An organic underlayer film (A layer) was obtained.
- the thin film forming composition resist underlayer film (B layer) forming composition] obtained in Examples 1 to 15, Examples 18 to 19, and Comparative Example 2 was applied and heated at 240 ° C. on a hot plate. By baking for 45 seconds, the thin film [resist underlayer film (B layer)] of the present invention was obtained.
- the film thickness of the thin film [resist underlayer film (B layer)] of the present invention was 25 nm.
- An organic resist underlayer film (C layer) forming composition obtained by the above formula (11-1) was applied thereon, baked on a hot plate at 205 ° C. for 60 seconds, and an organic resist underlayer film having a film thickness of 25 nm ( C layer) was obtained.
- a commercially available photoresist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR855) was applied on each of the films using a spinner, and baked on a hot plate at 100 ° C. for 60 seconds to form a 120 nm thick photoresist film (D layer ) was formed.
- Patterning of the resist was performed using an ArF exposure machine S-307E (wavelength: 193 nm, NA, ⁇ : 0.85, 0.93 / 0.85 (Dipole) immersion liquid: water) manufactured by NIKON.
- the target was exposed through a mask set so as to form a so-called line and space (dense line) in which the line width of the photoresist and the width between the lines were 0.065 ⁇ m after development.
- the resultant was baked on a hot plate at 105 ° C. for 60 seconds, cooled, and developed with an aqueous tetramethylammonium hydroxide solution (developer) having a concentration of 2.38% by mass in a single paddle process for 60 seconds.
- developer aqueous tetramethylammonium hydroxide solution
- the organic underlayer film (A layer) forming composition obtained by the above formula (10-1) was applied on a silicon wafer, baked on a hot plate at 240 ° C. for 60 seconds, and an organic underlayer film (A Layer).
- the thin film forming composition (resist underlayer film forming composition) solutions prepared in Examples 1 to 15, Examples 18 to 19 and Comparative Example 2 of the present invention were spin-coated, and 240 ° C. for 1 minute.
- a thin film [resist underlayer film (B layer)] (25 nm) was formed by heating.
- an EUV resist solution methacrylate resin resist
- D EUV resist layer
- the thin film forming compositions of the present invention prepared in Examples 16 to 17 were each applied onto a silicon wafer using a spinner. Heating was performed at 240 ° C. for 1 minute on a hot plate to form a thin film (resist upper layer film) (film thickness 0.05 ⁇ m) of the present invention. These thin films were subjected to a spectroscopic ellipsometer (manufactured by JA Woollam, VUV-VASE VU-302), using a refractive index (n value) and an optical extinction coefficient (k value, wavelength 193, 200, 248 nm). Also called attenuation coefficient).
- the thin film by the thin film forming composition of the present invention is applied to the upper layer of the EUV resist (EUV out-of-band radiation absorbing film) or the reverse material when applied to the reverse material, mixing with the resist needs to be prevented.
- a commercially available photoresist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR855) was applied to a silicon wafer with a spinner, and baked on a hot plate at 100 ° C. for 60 seconds to form a 0.10 ⁇ m-thick photoresist film. Formed.
- the solutions of the thin film forming compositions prepared in Examples 16 to 17 and Comparative Example 1 were applied onto the resist using a spinner. Heating was performed at 100 ° C.
- the thin film by the thin film forming composition of the present invention can be applied to an EUV resist upper layer film (EUV out-of-band radiation absorbing film) or a reverse material.
- EUV resist upper layer film EUV out-of-band radiation absorbing film
- the thin film by the thin film forming composition of the present invention When applying the thin film by the thin film forming composition of the present invention to the EUV resist upper layer film (EUV out-of-band radiation absorbing film), it is necessary to remove it with a developer after exposure. Therefore, it is necessary to dissolve with a developer.
- the solutions of the thin film forming composition (EUV resist upper layer film forming composition) prepared in Examples 16 to 17 and Comparative Example 1 were respectively applied to a silicon wafer by a spinner, and baked on a hot plate at 100 ° C. for 60 seconds. An EUV resist upper layer film having a thickness of 100 nm was formed.
- the thin film by the thin film forming composition of the present invention can be applied to the EUV resist upper layer film (EUV out-of-band radiation absorbing film).
- the above organic underlayer film forming composition [polymer-containing composition containing a unit structure represented by the above formula (10-1)] was applied on a silicon wafer and heated on a hot plate at 215 ° C. for 1 minute to form a film. A 200 nm thick organic underlayer film (A layer) was formed. On top of that, the thin film forming compositions (resist underlayer film forming compositions) of Examples 1 to 15, 18 to 19 and Comparative Examples 1 and 2 were applied, and the temperature was set to 1 at 240 ° C. on a hot plate. The film was heated for 30 minutes to form a thin film [resist underlayer film (B layer)] having a thickness of 20 nm.
- a commercially available photoresist solution (product name: FAiRS-9521NT05, manufactured by Fuji Film Co., Ltd.) was applied to each of them with a spinner, and heated on a hot plate at 100 ° C. for 1 minute to form a 85 nm-thick photoresist film ( C layer) was formed. Subsequently, using an NSR-S307E scanner (wavelength: 193 nm, NA, ⁇ : 0.85, 0.93 / 0.85) manufactured by Nikon Corporation, the line width of the photoresist and the width between the lines are 0 after development.
- the thin film by the thin film forming composition of the present invention can be applied to the lower layer film of the solvent developing resist.
- the thin film forming composition of the present invention includes a resist underlayer film forming composition such as a photoresist, a resist underlayer film forming composition such as an EUV resist, an EUV resist upper layer film forming composition, a reverse material forming composition, and a solvent developing resist underlayer. It can be used for a film-forming composition or the like.
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Abstract
Description
また、EUVレジストの上層に被覆してEUV帯域外の波長光を吸収する薄膜を形成するための組成物に関する。
下記式(2):
第2観点として、前記薄膜形成組成物が、上記式(1)で表される化合物、チタンキレート化合物、及び加水分解性チタンダイマーからなる群から選ばれるチタン化合物(A)と、上記式(2)で表されるシリコン化合物(B)と下記式(3):
第3観点として、前記窒素原子含有環基若しくはそれを含む有機基が、式(4):
第4観点として、前記窒素原子含有環基若しくはそれを含む有機基がイミダゾール基又はイミダゾール基を含む有機基である、第1観点又は第2観点に記載の薄膜形成組成物、
第5観点として、前記縮合芳香族環基若しくはそれを含む有機基がナフチル基又はアントリル基である、第1観点又は第2観点に記載の薄膜形成組成物、
第6観点として、前記保護されたフェノール性ヒドロキシ基若しくはそれを含む有機基がアルコキシアルキル置換アリール基又はアルコキシアルコキシアルキル置換アリール基である、第1観点又は第2観点に記載の薄膜形成組成物、
第7観点として、前記ビスアリール基若しくはそれを含む有機基がビスフェニル基である、第1観点又は第2観点に記載の薄膜形成組成物、
第8観点として、更にβジケトン及び/又はβケトエステルを含む、第1観点乃至第7観点のいずれか一つに記載の薄膜形成組成物、
第9観点として、更に酸を含む、第1観点乃至第8観点のいずれか一つに記載の薄膜形成組成物、
第10観点として、更に塩を含む、第1観点乃至第9観点のいずれか一つに記載の薄膜形成組成物、
第11観点として、更に水を含む、第1観点乃至第10観点のいずれか一つに記載の薄膜形成組成物、
第12観点として、第1観点乃至第11観点のいずれか一つに記載の薄膜形成組成物を半導体基板上に塗布し焼成することによって得られる薄膜。
第13観点として、第1観点乃至第11観点のいずれか一つに記載の薄膜形成組成物を半導体基板上に塗布し、焼成して薄膜を形成する工程、該薄膜上にレジスト用組成物を塗布してレジスト膜を形成する工程、該レジスト膜を露光する工程、露光後に該レジスト膜を現像しレジストパターンを得る工程、該レジストパターンにより薄膜をエッチングする工程、及びパターン化されたレジスト膜と薄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14観点として、半導体基板上に有機下層膜を形成する工程、該有機下層膜上に第1観点乃至第11観点のいずれか一つに記載の薄膜形成組成物を塗布し、焼成して薄膜を形成する工程、該薄膜上にレジスト用組成物を塗布してレジスト膜を形成する工程、該レジスト膜を露光する工程、露光後に該レジスト膜を現像しレジストパターンを得る工程、該レジストパターンにより薄膜をエッチングする工程、パターン化された薄膜により有機下層膜をエッチングする工程、及びパターン化された有機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15観点として、半導体基板上に有機下層膜を形成する工程、該有機下層膜上に第1観点乃至第11観点のいずれか一つに記載の薄膜形成組成物を塗布し、焼成して薄膜を形成する工程、該薄膜上に有機レジスト下層膜形成組成物を塗布して有機レジスト下層膜を形成する工程、該有機レジスト下層膜上にレジスト用組成物を塗布してレジスト膜を形成する工程、該レジスト膜を露光する工程、露光後に該レジスト膜を現像しレジストパターンを得る工程、該レジストパターンにより有機レジスト下層膜をエッチングする工程、パターン化された有機レジスト下層膜により薄膜をエッチングする工程、パターン化された薄膜により有機下層膜をエッチングする工程、及びパターン化された有機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、基板上にレジストパターンを形成する工程、その上に第1観点乃至第11観点のいずれか一つに記載の薄膜形成組成物を塗布し、焼成して薄膜を形成する工程、該薄膜をエッチングしてレジスト表面を露出する工程、レジストパターンをエッチングしパターンを反転させる工程を含む半導体装置の製造方法、
第17観点として、レジストがEUVレジストである第13観点乃至第16観点のいずれか一つに記載の製造方法、
第18観点として、半導体基板上にEUVレジスト用組成物を塗布し、焼成してEUVレジスト膜を形成する工程、該EUVレジスト膜上に第1観点乃至第11観点のいずれか一つに記載の薄膜形成組成物を塗布して薄膜を形成する工程、EUVで露光する工程、露光後にEUVレジストを現像しレジストパターンを得る工程、レジストパターン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である。
例えばレジストパターンが形成され、その下層に存在している本発明の薄膜をハロゲン含有ガスでドライエッチングして薄膜にパターンを転写し、その薄膜に転写されたパターンでハロゲン含有ガスを用いて基板加工を行う。あるいは、パターン転写された薄膜を用いて、その下層の有機下層膜を酸素系ガスでドライエッチングして有機下層膜にパターン転写を行って、そのパターン転写された有機下層膜で、ハロゲン含有ガスを用いて基板加工を行う。
そして、無機ポリマー(中間膜)は、その下に存在する有機下層膜のエッチングや、基板の加工(エッチング)にハードマスクとして有効である。即ち、基板加工時や有機下層膜の酸素系ドライエッチングガスに対して十分な耐ドライエッチング性を有するものである。
本発明の薄膜は、これらの上層レジストに対するドライエッチング速度の向上と、基板加工時等の耐ドライエッチング性を具備するものである。
200~240nm付近の波長光を除去するためにリソグラフィーシステムにフィルターを設置する方法もあるが工程上複雑になる。本発明ではEUV露光光に含まれるOUT of BAND光(帯域外放射)のなかでも200~240nmの望まれないDUV光をレジスト上層の薄膜で吸収し、EUVレジストの解像性の向上を行うことができる。この200~240nm付近のDUV光は選択的に酸化チタンが効率よく吸収するため、EUVレジスト上層の薄膜に用いられる無機ポリマーは酸化チタンを含むことが好ましい。
そして、露光後の現像時にEUVレジストと共に現像液(例えば、アルカリ性現像液)に溶解可能であるために、現像液による溶解除去が可能である。
また、本発明は、上記式(1)で表される化合物、チタンキレート化合物、及び加水分解性チタンダイマーからなる群から選ばれるチタン化合物(A)と、上記式(2)で表されるシリコン化合物(B)と、上記式(3)で表されるシリコン化合物(C)との混合物、その混合物の加水分解物、又はその混合物の加水分解縮合物を含む組成物であって、該組成物中のTi原子とSi原子に換算した合計モル数に対してTi原子のモル数が50乃至90%、好ましくは55%乃至90%、より好ましくは60%乃至90%である、リソグラフィー工程でレジストと共に用いる薄膜形成組成物である。
本発明の薄膜形成組成物は、上記式(1)で表される化合物、チタンキレート化合物、及び加水分解性チタンダイマーからなる群から選ばれるチタン化合物(A)と、上記式(2)で表されるシリコン化合物(B)と、上記式(3)で表されるシリコン化合物(C)との混合物、その混合物の加水分解物、又はその混合物の加水分解縮合物と、溶剤とを含む。
そして任意成分として酸、水、アルコール、硬化触媒、酸発生剤、他の有機ポリマー、吸光性化合物、及び界面活性剤等を含むことができる。
本発明の薄膜形成組成物における固形分は、例えば0.1乃至50質量%、又は0.1質量%30質量%、又は0.1質量%25質量%である。ここで固形分とは薄膜形成組成物の全成分から溶剤成分を除いたものである。
固形分中に占める加水分解性チタン、加水分解性オルガノシラン、その加水分解物、及びその加水分解縮合物の割合は、20質量%以上であり、例えば50乃至100質量%、又は60乃至100質量%、又は70乃至100質量%である。
式(1)で表される化合物は、aが0である場合に好ましく用いることができる。
また炭素原子数1乃至10のアルキレン基は、上述のアルキル基から誘導されるアルキレン基を例示することができる。
式(1)で表される化合物(加水分解性チタン化合物)としては、例えばテトラメトキシチタン、テトラエトキシチタン、テトライソプロポキシチタン、テトラノルマルブトキシチタン、テトライソブトキシチタン、テトラ-2-エチルヘキソキシドチタン、テトラキス(メトキシプロポキシ)チタン、テトラフェノキシチタン、テトラベンジロキシチタン、テトラフェニルエトキシチタン、テトラフェノキシエトキシチタン、テトラナフチロキシチタン、テトラ-2-エチルヘキソキシチタン、モノエトキシトリイソプロポキシチタン、ジイソプロポキシジイソブトキシチタン、アリロキシ(ポリエチレンオキシ)トリスイソプロポキシチタン、チタニウムクロライドトリイソプロポキサイド、チタニウムジクロライドジエトキサイド、チタニウム2-エチルヘキソキサイド、チタニウムヨードトリイソプロポキサイド、チタニウムテトラメトキシプロポキサイド、チタニウムテトラメチルフェノキサイド、チタニウムn-ノニロキサイド、チタニウムテトラステアリルオキサイド、チタニウムトリイソステアロイルモノイソプロポキサイド等のアルコキシチタンが挙げられる。
また、テトラメチルカルボニルオキシチタン、テトラエチルカルボニルオキシチタン、テトラn-プロピルカルボニルオキシチタン、テトラi-プロピルカルボニルオキシチタン、メチルカルボニルオキシトリエチルカルボニルオキシチタン、ジエチルカルボニルオキシジi-プロピルカルボニルオキシチタン等のアシルオキシチタンが挙げられる。
また、四フッ化チタン、四塩化チタン、四臭化チタン、四ヨウ化チタン等のハロゲン化チタンが挙げられる。
そして、チタン化合物(A)は式(1)で表される化合物からなる群から選ばれるチタン化合物を好ましく用いることができる。
アルコキシ基、アシルオキシ基、及びハロゲン原子は上述を例示することができる。
式(4)において、R7は水素原子、又は炭素原子数1乃至10のアルキル基、アルケニル基、エポキシ基、スルホニル基、若しくはそれらを含む有機基を表し、R8は炭素原子数1乃至10のアルキレン基、ヒドロキシアルキレン基、スルフィド結合、エーテル結合、エステル結合、又はそれらの組み合わせを表す。
X1は式(5)、式(6)、又は式(7)を表す。
式(5)、式(6)、及び式(7)において、R9乃至R13はそれぞれ独立して水素原子、又は炭素原子数1乃至10のアルキル基、アルケニル基、エポキシ基、スルホニル基、若しくはそれらを含む有機基を表す。
また、上記縮合芳香族環基若しくはそれを含む有機基としては、ナフチル基、又はアントリル基を挙げることができる。縮合芳香族環基を用いることによりアウトオブバンドの吸収を高めることができる。
また、上記保護されたフェノール性ヒドロキシ基若しくはそれを含む有機基としては、アルコキシアルキル置換アリール基、又はアルコキシアルコキシアルキル置換アリール基を挙げることができる。保護されたフェノール性ヒドロキシ基を用いることにより酸性度が向上してレジストプロファイルを向上させることができる。
また、上記ビスアリール基若しくはそれを含む有機基としては、ビスフェニル基を挙げることができる。
スルホンアミド基としては、フェニルスルホンアミド基、メチルスルホンアミド基を例示することができる。
また、加水分解性基の1モル当たり0.001乃至10モル、好ましくは0.001乃至1モルの加水分解触媒を用いることができる。
加水分解と縮合を行う際の反応温度は、通常20乃至120℃である。
加水分解は完全に加水分解を行うことも、部分加水分解することでも良い。即ち、加水分解縮合物中に加水分解物やモノマーが残存していても良い。
加水分解し縮合させる際に触媒を用いることができる。
加水分解触媒としては、金属キレート化合物、有機酸、無機酸、有機塩基、無機塩基を挙げることができる。
そして本発明のリソグラフィー工程に用いる薄膜形成組成物では、安定化のために酸(有機酸)、塩、水、アルコール、又はそれらの組み合わせを添加することができる。
また加える水は純水、超純水、イオン交換水等を用いることができ、その添加量は薄膜形成組成物100質量部に対して1乃至20質量部とすることができる。
βジケトン及び/又はβケトエステルとしては、例えば、アセチルアセトン、アセト酢酸メチル、アセト酢酸エチル、アセト酢酸n―プロピル、アセト酢酸i-プロピル、アセト酢酸n-ブチル、アセト酢酸i-ブチル、アセト酢酸sec-ブチル、アセト酢酸t-ブチル、2,4-ヘキサンジオン、2,4-ペンタンジオン、2,4-ヘプタンジオン、3,5-ヘプタンジオン、2,4-オクタンジオン、3,5-オクタンジオン、2,4-ノナンジオン、3,5-ノナンジオン、5-メチル-2,4-ヘキサンジオン等を挙げることができる。これらの化合物のうち、アセチルアセトン、アセト酢酸エチルが好ましい。この成分は、単独でまたは2種以上を混合して使用することができる。このβジケトン及び/又はβケトエステルは、縮合物(ポリチタノキサン、ポリオルガノシロキサン、共重合ポリマー、又はそれらの組み合わせ)100質量部に対して1乃至2000質量部、又は10乃至500質量部で使用することができる。
好ましいビスフェノールS、又はビスフェノールS誘導体は以下に例示される。
塩としては、アンモニウム塩、ホスフィン類、ホスホニウム塩、スルホニウム塩を用いることができる。
式(E-2):
式(E-3):
式(E-4):
式(E-5):
式(E-6):
また陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
この第4級アンモニウム塩は、市販品として入手する事が可能であり、例えばテトラメチルアンモニウムアセテート、テトラブチルアンモニウムアセテート、塩化トリエチルベンジルアンモニウム、臭化トリエチルベンジルアンモニウム、塩化トリオクチルメチルアンモニウム、塩化トリブチルベンジルアンモニウム、塩化トリメチルベンジルアンモニウム等が挙げられる。
陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
この化合物は、市販品として入手する事も出来るが、例えば1-メチルイミダゾール、1-ベンジルイミダゾール等のイミダゾール系化合物と、臭化ベンジル、臭化メチル等のハロゲン化アルキルやハロゲン化アリールを反応させて製造する事ができる。
陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
この化合物は、市販品として入手する事も可能であり、或いは、例えばピリジンと、塩化ラウリル、塩化ベンジル、臭化ベンジル、臭化メチル、臭化オクチル等のハロゲン化アルキル、又はハロゲン化アリールを反応させて製造する事が出来る。この化合物としては例えば、塩化N-ラウリルピリジニウム、臭化N-ベンジルピリジニウム等を挙げる事が出来る。
陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
この化合物は市販品として入手する事も可能であり、或いは、例えばピコリン等の置換ピリジンと、臭化メチル、臭化オクチル、塩化ラウリル、塩化ベンジル、臭化ベンジル等のハロゲン化アルキル、又はハロゲン化アリールを反応させて製造する事が出来る。この化合物としては例えば、N-ベンジルピコリニウムクロライド、N-ベンジルピコリニウムブロマイド、N-ラウリルピコリニウムクロライド等を挙げることが出来る。
また陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
この化合物は、アミンとカルボン酸やフェノール等の弱酸との反応によって製造する事が出来る。
カルボン酸としてはギ酸や酢酸が挙げられ、ギ酸を使用した場合は、陰イオン(Y-)は(HCOO-)であり、酢酸を使用した場合は、陰イオン(Y-)は(CH3COO-)である。またフェノールを使用した場合は、陰イオン(Y-)は(C6H5O-)である。
また陰イオン(Y-)としては、塩素イオン(Cl-)、臭素イオン(Br-)、ヨウ素イオン(I-)等のハロゲンイオンや、カルボキシラート(-COO-)、スルホナト(-SO3 -)、アルコラート(-O-)等の酸基を挙げることが出来る。
有機ポリマー化合物としては特に制限はなく、種々の有機ポリマーを使用することができる。縮重合ポリマー及び付加重合ポリマー等を使用することができる。ポリエステル、ポリスチレン、ポリイミド、アクリルポリマー、メタクリルポリマー、ポリビニルエーテル、フェノールノボラック、ナフトールノボラック、ポリエーテル、ポリアミド、ポリカーボネート等の付加重合ポリマー及び縮重合ポリマーを使用することができる。
中でも、吸光部位として機能するベンゼン環、ナフタレン環、アントラセン環、トリアジン環、キノリン環、及びキノキサリン環等の芳香環構造を有する有機ポリマーが好ましく使用される。
グリコール化合物としてはジエチレングリコール、ヘキサメチレングリコール、ブチレングリコール等が挙げられる。
ジカルボン酸化合物としては、コハク酸、アジピン酸、テレフタル酸、無水マレイン酸等が挙げられる。
また、縮重合ポリマーとしては、例えば、ポリピロメリットイミド、ポリ(p-フェニレンテレフタルアミド)、ポリブチレンテレフタレート、ポリエチレンテレフタレート等のポリエステル、ポリアミド、ポリイミドが挙げられる。
有機ポリマー化合物は一種のみを使用することができ、または二種以上を組み合わせて使用することができる。
有機ポリマー化合物が使用される場合、その割合としては、縮合物(ポリチタノキサン、ポリオルガノシロキサン、共重合ポリマー、又はそれらの組み合わせ)100質量部に対して、1乃至200質量部、または5乃至100質量部、または10乃至50質量部、または20乃至30質量部である。
酸発生剤としては、熱酸発生剤や光酸発生剤が挙げられる。
光酸発生剤は、レジストの露光時に酸を生ずる。そのため、下層膜の酸性度の調整ができる。これは、下層膜の酸性度を上層のレジストとの酸性度に合わせるための一方法である。また、下層膜の酸性度の調整によって、上層に形成されるレジストのパターン形状の調整ができる。
本発明の薄膜形成組成物に含まれる光酸発生剤としては、オニウム塩化合物、スルホンイミド化合物、及びジスルホニルジアゾメタン化合物等が挙げられる。
光酸発生剤を使用する場合、その割合としては、縮合物(ポリチタノキサン、ポリオルガノシロキサン、共重合ポリマー、又はそれらの組み合わせ)100質量部に対して、0.01乃至5質量部、または0.1乃至3質量部、または0.5乃至1質量部である。
本発明の薄膜形成組成物に含まれる界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類、ポリオキシエチレンオクチルフェノールエーテル、ポリオキシエチレンノニルフェノールエーテル等のポリオキシエチレンアルキルアリルエーテル類、ポリオキシエチレン・ポリオキシプロピレンブロックコポリマー類、ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタントリオレエート、ソルビタントリステアレート等のソルビタン脂肪酸エステル類、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレエート、ポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤、商品名エフトップEF301、EF303、EF352((株)トーケムプロダクツ製)、商品名メガファックF171、F173、R-08、R-30(大日本インキ化学工業(株)製)、フロラードFC430、FC431(住友スリーエム(株)製)、商品名アサヒガードAG710,サーフロンS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(株)製)等のフッ素系界面活性剤、及びオルガノシロキサンポリマ-KP341(信越化学工業(株)製)等を挙げることができる。
これらの溶剤は単独で、または二種以上の組み合わせで使用することができる。
以下、本発明の薄膜形成組成物をレジスト下層膜形成組成物として使用した場合について説明する。
半導体装置の製造に使用される基板(例えば、シリコンウエハー基板、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、ガラス基板、ITO基板、ポリイミド基板、及び低誘電率材料(low-k材料)被覆基板等)の上に、スピナー、コーター等の適当な塗布方法により本発明の薄膜形成組成物(レジスト下層膜形成組成物)が塗布され、その後、焼成することにより薄膜(レジスト下層膜)が形成される。
焼成する条件としては、焼成温度80℃乃至500℃、又は80℃乃至250℃、焼成時間0.3乃至60分間の中から適宜、選択される。好ましくは、焼成温度150℃乃至500℃、焼成時間0.5乃至2分間である。
ここで、形成される薄膜(レジスト下層膜)の膜厚としては、例えば、10乃至1000nmであり、または20乃至500nmであり、または50乃至300nmであり、または100乃至200nmであり、または10乃至100nmである。
フォトレジスト層の膜厚としては例えば50乃至10000nmであり、または100乃至2000nmであり、または200乃至1000nmであり、または30乃至200nmである。
例えば、フォトレジストに対して十分に早いエッチング速度となるフッ素系ガスをエッチングガスとして本発明の薄膜(レジスト下層膜)に加工が可能であり、また本発明の薄膜(レジスト下層膜)に対して十分に早いエッチング速度となる酸素系ガスをエッチングガスとして有機下層膜の加工が可能であり、更に有機下層膜に対して十分に早いエッチング速度となるフッ素系ガスをエッチングガスとして基板の加工を行うことができる。
また、EUVレジストとしてはメタクリレート樹脂系レジストを用いることができる。
本発明の薄膜(レジスト下層膜)のドライエッチングには、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、一酸化炭素、アルゴン、酸素、窒素、六フッ化硫黄、ジフルオロメタン、三フッ化窒素及び三フッ化塩素、塩素、トリクロロボラン及びジクロロボラン等のガスを使用することができる。
なかでも、ハロゲン系ガスによるドライエッチングでは、基本的に有機物質からなるフォトレジストは除去されにくく、それに対し、ケイ素原子を多く含む本発明の薄膜(レジスト下層膜)はハロゲン系ガスによって速やかに除去されることから、レジスト下層膜のドライエッチングにはハロゲン系ガスを使用することが好ましい。これにより、薄膜(レジスト下層膜)のドライエッチングに伴うフォトレジストの膜厚の減少を抑えることができる。そして、その結果、フォトレジストを薄膜で使用することが可能となる。
レジスト下層膜のドライエッチングはフッ素系ガスにより行うこともできる。フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
本発明のチタン-シリコン含有薄膜(レジスト下層膜)のドライエッチングはハロゲン系ガスによることが好ましく、ハロゲン系ガスとしては、例えば、臭化水素(HBr)、塩素(Cl)などが挙げられ、CF4やCHF3などのフッ素系ガスやO2などの酸素系ガスとの混合によりレジストとのエッチング選択比を得ることが可能である。
フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
さらに、本発明の薄膜(レジスト下層膜)は、基板とフォトレジストとの相互作用を防止するための層、フォトレジストに用いられる材料又はフォトレジストへの露光時に生成する物質の基板への悪作用を防ぐ機能とを有する層、加熱焼成時に基板から生成する物質の上層フォトレジストへの拡散を防ぐ機能を有する層、及び半導体基板誘電体層によるフォトレジスト層のポイズニング効果を減少させるためのバリア層等として使用することも可能である。
また、本発明の薄膜形成組成物(レジスト下層膜形成組成物)より形成される薄膜(レジスト下層膜)は、デュアルダマシンプロセスで用いられるビアホールが形成された基板に適用され、ホールを隙間なく充填することができる埋め込み材として使用できる。また、凹凸のある半導体基板の表面を平坦化するための平坦化材として使用することもできる。
本発明におけるEUVレジスト上層膜の下層に塗布されるEUVレジストとしてはネガ型、ポジ型いずれも使用できる。酸発生剤と酸により分解してアルカリ溶解速度を変化させる基を有するバインダーからなる化学増幅型レジスト、アルカリ可溶性バインダーと酸発生剤と酸により分解してレジストのアルカリ溶解速度を変化させる低分子化合物からなる化学増幅型レジスト、酸発生剤と酸により分解してアルカリ溶解速度を変化させる基を有するバインダーと酸により分解してレジストのアルカリ溶解速度を変化させる低分子化合物からなる化学増幅型レジスト、EUVによって分解してアルカリ溶解速度を変化させる基を有するバインダーからなる非化学増幅型レジスト、EUVによって切断されアルカリ溶解速度を変化させる部位を有するバインダーからなる非化学増幅型レジストなどがある。
これらの中で好ましい現像液は第四級アンモニウム塩、さらに好ましくはテトラメチルアンモニウムヒドロキシド及びコリンである。
本発明の薄膜形成組成物(EUVレジスト上層膜形成組成物)を適用する半導体デバイスは、基板上に、パターンを転写する加工対象膜と、レジスト膜と、薄膜(EUVレジスト上層膜)が順に形成された構成を有する。この薄膜(EUVレジスト上層膜)は、下地基板やEUVによって及ぼされる悪影響を低減することにより、ストレート形状の良好なレジストパターンを形成し、充分なEUV照射量に対するマージンを得ることができる。また、本発明の薄膜(EUVレジスト上層膜)は、下層に形成されるレジスト膜と同等の大きなウエットエッチング速度を有し、ウエットエッチング工程によって加工対象である下地膜に容易にレジストパターンを転写することができる。
また、EUVレジストの下層膜として、EUVレジストとインターミキシングすることなく、EUV露光に際して好ましくない露光光、例えば上述のUVやDUVの基板又は界面からの反射を防止することができるEUVレジストの下層反射防止膜として、本発明の薄膜形成組成物(EUVレジスト下層膜形成組成物)を用いることができる。EUVレジストの下層で効率的に反射を防止することができる。EUVレジスト下層膜として用いた場合は、プロセスはフォトレジスト用下層膜と同様に行うことができる。
上記基板上に、スピナー、コーター等の適当な塗布方法により本発明の薄膜形成組成物を塗布し、その後、焼成することにより薄膜が形成される。本発明の薄膜を被覆する前に基板上に有機下層膜を形成し、その上に上記薄膜を形成することができる。
本発明の薄膜(レジスト下層膜)上に形成されるフォトレジストとしては、例えばArF光等の露光に使用される光に感光するものであれば特に限定されない。ネガ型フォトレジスト及びポジ型フォトレジストのいずれも使用できる。露光後、有機溶剤により現像することが可能なフォトレジストであれば使用可能である。
焼成する条件としては上記条件が適用できる。
次いでその薄膜上に、例えば上記フォトレジスト層(膜)が形成される。
さらに、これらの現像液に界面活性剤などを加えることもできる。現像の条件としては、温度5乃至50℃、時間10乃至600秒から適宜選択される。
本発明の薄膜のドライエッチングには、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、一酸化炭素、アルゴン、酸素、窒素、六フッ化硫黄、ジフルオロメタン、三フッ化窒素及び三フッ化塩素、塩素、トリクロロボラン及びジクロロボラン等のガスを使用することができる。
なかでも、ハロゲン系ガスによるドライエッチングでは、基本的に有機物質からなるフォトレジストは除去されにくく、それに対し、ケイ素原子を多く含む本発明の薄膜はハロゲン系ガスによって速やかに除去されることから、本発明の薄膜のドライエッチングにはハロゲン系ガスを使用することが好ましい。これにより、薄膜のドライエッチングに伴うフォトレジストの膜厚の減少を抑えることができる。そして、その結果、フォトレジストを薄膜で使用することが可能となる。
本発明の薄膜のドライエッチングはフッ素系ガスによることが好ましく、フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
例えば、フォトレジストに対して十分に早いエッチング速度となるフッ素系ガスをエッチングガスとして本発明の薄膜に加工が可能であり、また本発明の薄膜に対して十分に早いエッチング速度となる酸素系ガスをエッチングガスとして有機下層膜の加工が可能であり、更に有機下層膜に対して十分に早いエッチング速度となるフッ素系ガスをエッチングガスとして基板の加工を行うことができる。
テトライソブトキシチタン18.60g(70mol%)、メチルトリエトキシシラン3.48g(25mol%)、3-(トリエトキシシリルプロピル)ジアリルイソシアヌレート1.62g(5mol%)、アセトン35.55g、アセチルアセトン35.55gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸5.21gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw700であった。
テトライソブトキシチタン11.59g(50mol%)、メチルトリエトキシシラン4.49g(37mol%)、3-(トリエトキシシリルプロピル)ジアリルイソシアヌレート0.85g(3mol%)、フェニルトリメトキシシラン1.35g(10mol%)、アセトン27.42g、アセチルアセトン27.42gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸4.30gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン36.00gを加え、反応副生物であるエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-2)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw900であった。
テトライソプロポキシチタン17.85g(70mol%)、メチルトリエトキシシラン3.20g(20mol%)、ビフェニル-4-イルトリメトキシシラン2.40g(10mol%)、アセトン35.26g、アセチルアセトン35.26gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸5.98gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるメタノールとエタノール、アセトン、イソプロパノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-3)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw800であった。
テトライソプロポキシチタン18.01g(70mol%)、メチルトリエトキシシラン3.23g(20mol%)、1-ナフチルトリメトキシシラン2.25g(10mol%)、アセトン35.24g、アセチルアセトン35.24gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸6.04gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン46.00gを加え、反応副生物であるメタノールとエタノール、アセトン、イソプロパノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-4)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw800であった。
テトライソプロポキシチタン17.63g(70mol%)、メチルトリエトキシシラン3.16g(20mol%)、6-(メトキシメトキシ)-2-(トリメトキシシリル)ナフタレン2.73g(10mol%)、アセトン35.28g、アセチルアセトン35.28gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸5.91gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるメタノールとエタノール、アセトン、イソプロパノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-5)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw800であった。
テトライソブトキシチタン18.59g(70mol%)、メチルトリエトキシシラン3.44g(24.7mol%)、3-(トリエトキシシリルプロピル)ジアリルイソシアヌレート1.61g(5mol%)、N-(3-トリエトキシシリプロピル)-4,5-ジヒドロイミダゾール0.06g(0.3mol%)、アセトン35.55g、アセチルアセトン35.55gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.10mol/Lの塩酸5.21gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-6)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw800であった。
テトライソブトキシチタン18.74g(70mol%)、メチルトリエトキシシラン3.46g(24.7mol%)、3-(トリエトキシシリルプロピル)ジメチルイソシアヌレート1.42g(5mol%)、N-(3-トリエトキシシリプロピル)-4,5-ジヒドロイミダゾール0.065g(0.3mol%)、アセトン35.53g、アセチルアセトン35.53gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.10mol/Lの塩酸5.25gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-7)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw800であった。
テトライソブトキシチタン15.60g(60mol%)、テトラエトキシシラン1.91g(10mol%)、メチルトリエトキシシラン4.08g(25mol%)、3-(トリエトキシシリルプロピル)ジアリルイソシアヌレート1.89g(5mol%)、アセトン35.21g、アセチルアセトン35.21gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸6.10gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(8-8)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1000であった。
テトライソプロポキシチタニウム17.73g(50mol%)、メチルトリエトキシシラン7.75g(45mol%)、3-(トリエトキシシリルプロピル)ジアリルイソシアヌレート2.00g(5mol%)、アセトン35.22g、アセチルアセトン35.22gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸6.09gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるエタノール、アセトン、イソプロパノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよび4-メチル2-ペンタノールを加え、アセチルアセトン/4-メチル2-ペンタノール5/95の溶媒比率として140℃における固形残物換算で8質量パーセントとなるように調整した。得られたポリマー式(8-1)のGPCによる重量平均分子量はポリスチレン換算でMw800であった。
テトライソブトキシチタニウム18.60g(70mol%)、メチルトリエトキシシラン3.48g(25mol%)、3-(トリエトキシシリルプロピル)ジアリルイソシアヌレート1.62g(5mol%)、アセトン35.55g、アセチルアセトン35.55gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸5.21gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよび4-メチル2-ペンタノールを加え、アセチルアセトン/4-メチル2-ペンタノール5/95の溶媒比率として140℃における固形残物換算で8質量パーセントとなるように調整した。得られたポリマー式(8-1)のGPCによる重量平均分子量はポリスチレン換算でMw700であった。
テトラエトキシシラン16.70g(70mol%)、メチルトリエトキシシラン5.14g(25mol%)、フェニルトリメトキシシラン1.14g(5mol%)、アセトン69.24gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸7.68gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にプロピレングリコールモノエチルエーテル46.00gを加え、反応副生物であるメタノールとエタノール、アセトン、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)プロピレングリコールモノエチルエーテル溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマーは式(9-1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1200であった。
テトライソブトキシチタン19.25g(70mol%)、メチルトリエトキシシラン3.60g(25mol%)、フェニルトリメトキシシラン0.80g(5mol%)、アセトン35.48g、アセチルアセトン35.48gを300mLのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01mol/Lの塩酸5.39gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で240分反応させた。その後、反応溶液を室温まで冷却し、反応溶液にアセチルアセトン48.00gを加え、反応副生物であるメタノールとエタノール、アセトン、イソブタノール、水、塩酸を減圧留去し、濃縮して加水分解縮合物(ポリマー)アセチルアセトン溶液を得た。アセチルアセトンおよびプロピレングリコールモノエチルエーテルを加え、アセチルアセトン/プロピレングリコールモノエチルエーテル10/90の溶媒比率として140℃における固形残物換算で15質量パーセントとなるように調整した。得られたポリマー式(9-2)のGPCによる重量平均分子量はポリスチレン換算でMw1000であった。
[薄膜(レジスト下層膜)の調製]
上記合成例1乃至10並び比較合成例1及び2で得られたチタン-ケイ素含有ポリマー、酸、硬化触媒、添加剤、溶媒、水を表1に示す割合となるように混合し、0.1μmのフッ素樹脂製のフィルターで濾過することによって、薄膜形成組成物(レジスト下層膜形成組成物)の溶液をそれぞれ調製した。表1中のポリマーの添加割合はポリマー溶液の添加量ではなく、ポリマー自体の添加量を示した。
表1中でマレイン酸はMA、ベンジルトリエチルアンモニウムクロリドはBTAC、N-(3-トリエトキシシリプロピル)-4,5-ジヒドロイミダゾールはIMIDTEOS、トリフェニルスルホニウムトリフルオロメタンスルホネートはTPS105、マレイン酸モノトリフェニルスルフォニウムはTPSMA、プロピレングリコールモノメチルエーテルアセテートはPGMEA、プロピレングリコールモノエチルエーテルはPGEE、プロピレングリコールモノメチルエーテルはPGME、アセチルアセトンはAcAc、4-メチル2-ペンタノール(即ち、メチルイソブチルカルビノール)はMIBCと略した。水は超純水を用いた。各添加量は質量部で示した。
窒素下、100mL四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9-フルオレノン(7.28g、0.040mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、1,4-ジオキサン(6.69g、関東化学(株)製)を仕込み撹拌し、100℃まで昇温し溶解させ重合を開始した。24時間後60℃まで放冷後、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とするポリマー(式(10-1)、以下PCzFLと略す)9.37gを得た。
1H-NMR(400MHz,DMSO-d6):δ7.03-7.55(br,12H),δ7.61-8.10(br,4H),δ11.18(br,1H)
PCzFLの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2800、多分散度Mw/Mnは1.77であった。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)製)100g、5,5-ジエチルバルビツール酸66.4gをプロピレングリコールモノメチルエーテル682gに溶解させた後、反応液を140℃に加温し、同時に反応液中に窒素を流した。その後、触媒としてベンジルトリエチルアンモニウムクロリド4.1gを添加し、窒素雰囲気下で24時間攪拌した。得られた反応生成物のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は6800であった。
なお、本合成によって得られた反応生成物は、式(11-1)で表される構造単位を有する化合物が含まれるものと推定される。
実施例1乃至15、実施例18乃至19、比較例1及び2で調製した薄膜形成組成物(レジスト下層膜形成組成物)をスピナーを用い、シリコンウェハー上にそれぞれ塗布した。ホットプレート上で240℃1分間加熱し、薄膜(レジスト下層膜)(膜厚0.05μm)を形成した。そして、これらの薄膜(レジスト下層膜)を分光エリプソメーター(J.A.Woollam社製、VUV-VASE VU-302)を用い、波長193、200、248nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数とも呼ぶ)を測定した。
ドライエッチング速度の測定に用いたエッチャー及びエッチングガスは、以下の通りである。
RIE-10NR(サムコ製):O2
実施例1乃至15、実施例18乃至19、比較例1及び2で調製した薄膜形成組成物(レジスト下層膜形成組成物)の溶液をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上で240℃1分間加熱し、薄膜(レジスト下層膜)0.05μmをそれぞれ形成した。
また、同様に有機下層膜形成組成物をスピナーを用い、シリコンウェハー上に塗膜を形成(膜厚0.20μm)した。エッチングガスとしてO2ガスを使用してドライエッチング速度を測定し、実施例1乃至15、比較例1及び2の薄膜(レジスト下層膜)のドライエッチング速度との比較を行った。
上記で得られた有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で240℃で60秒間ベークし、膜厚200nmの有機下層膜(A層)を得た。その上に、実施例1乃至15、実施例18乃至19、比較例1及び2で得られた薄膜形成組成物[レジスト下層膜(B)形成組成物]を塗布し、ホットプレート上で240℃で45秒間ベークし、薄膜[レジスト下層膜(B層)]を得た。薄膜[レジスト下層膜(B層)]の膜厚は25nmであった。
その上に市販のフォトレジスト溶液(住友化学(株)製、商品名PAR855)をスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて60秒間ベークし、膜厚120nmのフォトレジスト膜(D層)を形成した。レジストのパターニングはNIKON社製ArF露光機S-307E(波長193nm、NA、σ:0.85、0.93/0.85(Dipole)液浸液:水)を用いて行った。ターゲットは現像後にフォトレジストのライン幅およびそのライン間の幅が0.065μmである、いわゆるラインアンドスペース(デンスライン)が形成されるように設定されたマスクを通して露光を行った。
その後、ホットプレート上で105℃にて60秒間ベークし、冷却後、60秒シングルパドル式工程にて2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液(現像液)で現像した。パターニングされたウェハを下記エッチングガスによりエッチングを行い、エッチング後の本発明の薄膜形状(レジスト下層膜形状)観察を行った。本発明の薄膜(レジスト下層膜)エッチングでのエッチングは、CF4ガスを用いて下記条件にて本発明の薄膜(レジスト下層膜)がエッチングされた事を確認し、その後O2/N2ガスによる有機レジスト下層膜のエッチングを行った。
RIE-10NR(サムコ製)
CF4:50sccm/Ar:200sccm、15Pa、200W
O2:10sccm/N2:20sccm、1Pa、300W、110秒
表2に193nmの波長での屈折率n1、光学吸収係数k1、220nmの波長での屈折率n2、光学吸収係数k2、248nmの波長での屈折率n3、光学吸収係数k3、エッチング後のパターン形状を示した。
上記エッチング後のパターン形状で肩落ち(ラウンディング)とは有機下層膜にパターンを転写する際、酸素系エッチングによりパターン肩落ちが生じ、丸くなる現象である。矩形であるほどパターンを良好に転写することが可能である。
実施例1乃至19、比較例1及び2で調製した薄膜形成組成物(レジスト下層膜形成組成物)の溶液をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上で240℃1分間加熱し、薄膜(レジスト下層膜)0.05μmをそれぞれ形成した。また有機下層膜形成組成物をスピナーを用い、シリコンウェハー上に有機下層膜を形成(膜厚0.20μm)した。また、同様にレジストをスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上で100℃1分間加熱し、レジスト膜0.10μmを形成した。
2300Versysエッチング装置とKiyo45チャンバー(ラムリサーチ製、商品名)を用い、ハロゲン系エッチングガスとしてHBr/Cl2/CF4/O2系ガスを用いて実施例1乃至19、比較例1及び2の薄膜(レジスト下層膜)のドライエッチング速度との比較を行った。RIE-10NR(サムコ製)を用い、エッチングガスとしてO2ガスを使用してドライエッチング速度を測定し、実施例1乃至19、比較例1及び2の薄膜(レジスト下層膜)のドライエッチング速度との比較を行った。
上記ハロゲン系ガスによるエッチング速度比(1)は(薄膜(レジスト下層膜(B層)))/(レジスト膜(D層))にて算出した。
酸素系ガス(O2ガス)耐性は、(薄膜(レジスト下層膜(B層)))/(有機下層膜(A層))のエッチング速度比(2)で示した。
4層プロセス評価として上記式(10-1)で得られた有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で400℃で60秒間ベークし、膜厚200nmの有機下層膜(A層)を得た。その上に、実施例1乃至15、実施例18乃至19、比較例2で得られた薄膜形成組成物[レジスト下層膜(B層)形成組成物]を塗布し、ホットプレート上で240℃で45秒間ベークし、本発明の薄膜[レジスト下層膜(B層)]を得た。本発明の薄膜[レジスト下層膜(B層)]の膜厚は25nmであった。その上に上記式(11-1)で得られた有機レジスト下層膜(C層)形成組成物を塗布し、ホットプレート上で205℃で60秒間ベークし、膜厚25nmの有機レジスト下層膜(C層)を得た。その上に市販のフォトレジスト溶液(住友化学(株)製、商品名PAR855)をスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて60秒間ベークし、膜厚120nmのフォトレジスト膜(D層)を形成した。
レジストのパターニングはNIKON社製ArF露光機S-307E(波長193nm、NA、σ:0.85、0.93/0.85(Dipole)液浸液:水)を用いて行った。ターゲットは現像後にフォトレジストのライン幅およびそのライン間の幅が0.065μmである、いわゆるラインアンドスペース(デンスライン)が形成されるように設定されたマスクを通して露光を行った。その後、ホットプレート上105℃で60秒間ベークし、冷却後、60秒シングルパドル式工程にて2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液(現像液)で現像した。
上記式(10-1)で得られた有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で240℃で60秒間ベークし、膜厚90nmの有機下層膜(A層)を得た。その上に、本発明の実施例1乃至15、実施例18乃至19、及び比較例2で調製された薄膜形成組成物(レジスト下層膜形成組成物)溶液をスピンコートし、240℃で1分間加熱することにより、薄膜[レジスト下層膜(B層)](25nm)を形成した。そのハードマスク上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をスピンコートし加熱を行いEUVレジスト層(D)層を形成し、EUV露光装置(Micro Exposure Tool 略称MET)を用い、NA=0.30、σ=0.36/0.68 Quadropoleの条件で露光した。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、現像及びリンス処理をし、レジストパターンを形成した。評価は、26nmのラインアンドスペースの形成可否、パターン断面観察によるパターン形状を評価した。
実施例16乃至17で調製した本発明の薄膜形成組成物をスピナーを用い、シリコンウェハー上にそれぞれ塗布した。ホットプレート上で240℃1分間加熱し、本発明の薄膜(レジスト上層膜)(膜厚0.05μm)を形成した。そして、これらの薄膜を分光エリプソメーター(J.A.Woollam社製、VUV-VASE VU-302)を用い、波長193、200、248nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数とも呼ぶ)を測定した。
本発明の薄膜形成組成物による薄膜を、EUVレジスト上層膜(EUV帯域外放射吸収膜)や、リバース材料に適用する時にレジスト上層に塗布するため、レジストとのミキシングが生じない必要がある。
市販のフォトレジスト溶液(住友化学(株)製、商品名PAR855)をシリコンウェハーにスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて60秒間ベークし、膜厚0.10μmのフォトレジスト膜を形成した。実施例16乃至17、比較例1で調製した薄膜形成組成物の溶液をスピナーを用い、レジスト上に塗布した。ホットプレート上で100℃1分間加熱し、薄膜形成組成物による薄膜0.10μmをそれぞれ形成した。レジストが塗布組成物に溶解してミキシングした場合を不良とし、塗布組成物に溶解せずに塗布可能であった場合を良好とした。
従って、本発明の薄膜形成組成物による薄膜は、EUVレジスト上層膜(EUV帯域外放射吸収膜)やリバース材料に適用できる。
本発明の薄膜形成組成物による薄膜を、EUVレジスト上層膜(EUV帯域外放射吸収膜)に適用する時には露光後、現像液にて除去される必要がある。その為、現像液にて溶解する必要がある。実施例16乃至17、比較例1で調製した薄膜形成組成物(EUVレジスト上層膜形成組成物)の溶液をシリコンウェハーにスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて60秒間ベークし、膜厚100nmのEUVレジスト上層膜を形成した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を塗布し、1分間保持した。その後、高速回転により現像液を振り切り、EUVレジスト上層膜が除去された場合、除去性良好とし、除去されなかった場合、あるいは溶け残りが生じた場合を除去性不良とした。
上述の有機下層膜形成組成物[上記式(10-1)で表される単位構造を含むポリマー含有組成物]をシリコンウエハー上に塗布し、ホットプレート上で215℃で1分間加熱し、膜厚200nmの有機下層膜(A層)を形成した。
その上に、実施例1乃至実施例15、実施例18乃至実施例19、比較例1及び2の薄膜形成組成物(レジスト下層膜形成組成物)を塗布し、ホットプレート上で240℃で1分間加熱し、膜厚20nmの薄膜[レジスト下層膜(B層)]を形成した。その上に市販のフォトレジスト溶液(富士フイルム(株)製、商品名FAiRS-9521NT05)をスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて1分間加熱し、膜厚85nmのフォトレジスト膜(C層)を形成した。
続いて、(株)ニコン製NSR-S307Eスキャナー(波長193nm、NA、σ:0.85、0.93/0.85)を用い、現像後にフォトレジストのライン幅及びそのライン間の幅が0.065μm、すなわち0.065μmのラインアンドスペース(L/S)=1/1のデンスラインが形成されるように設定されたマスクに通して露光を行った。その後、ホットプレート上100℃で60秒間ベークし、冷却後、酢酸ブチル(溶剤現像液)を用いて60秒現像し、薄膜[レジスト下層膜(B層)]上にネガ型のパターンを形成した。
得られたフォトレジストパターンについて、大きなパターン剥がれやアンダーカットが発生しないものを良好と評価した。
Claims (18)
- 下記式(1):
下記式(2):
- 前記薄膜形成組成物が、上記式(1)で表される化合物、チタンキレート化合物、及び加水分解性チタンダイマーからなる群から選ばれるチタン化合物(A)と、上記式(2)で表されるシリコン化合物(B)と下記式(3):
- 前記窒素原子含有環基若しくはそれを含む有機基が、式(4):
- 前記窒素原子含有環基若しくはそれを含む有機基がイミダゾール基又はイミダゾール基を含む有機基である、請求項1又は請求項2に記載の薄膜形成組成物。
- 前記縮合芳香族環基若しくはそれを含む有機基がナフチル基又はアントリル基である、請求項1又は請求項2に記載の薄膜形成組成物。
- 前記保護されたフェノール性ヒドロキシ基若しくはそれを含む有機基がアルコキシアルキル置換アリール基又はアルコキシアルコキシアルキル置換アリール基である、請求項1又は請求項2に記載の薄膜形成組成物。
- 前記ビスアリール基若しくはそれを含む有機基がビスフェニル基である、請求項1又は請求項2に記載の薄膜形成組成物。
- 更にβジケトン及び/又はβケトエステルを含む、請求項1乃至請求項7のいずれか1項に記載の薄膜形成組成物。
- 更に酸を含む、請求項1乃至請求項8のいずれか1項に記載の薄膜形成組成物。
- 更に塩を含む、請求項1乃至請求項9のいずれか1項に記載の薄膜形成組成物。
- 更に水を含む、請求項1乃至請求項10のいずれか1項に記載の薄膜形成組成物。
- 請求項1乃至請求項11のいずれか1項に記載の薄膜形成組成物を半導体基板上に塗布し焼成することによって得られる薄膜。
- 請求項1乃至請求項11のいずれか1項に記載の薄膜形成組成物を半導体基板上に塗布し、焼成して薄膜を形成する工程、該薄膜上にレジスト用組成物を塗布してレジスト膜を形成する工程、該レジスト膜を露光する工程、露光後に該レジスト膜を現像しレジストパターンを得る工程、該レジストパターンにより薄膜をエッチングする工程、及びパターン化されたレジスト膜と薄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。
- 半導体基板上に有機下層膜を形成する工程、該有機下層膜上に請求項1乃至請求項11のいずれか1項に記載の薄膜形成組成物を塗布し、焼成して薄膜を形成する工程、該薄膜上にレジスト用組成物を塗布してレジスト膜を形成する工程、該レジスト膜を露光する工程、露光後に該レジスト膜を現像しレジストパターンを得る工程、該レジストパターンにより薄膜をエッチングする工程、パターン化された薄膜により有機下層膜をエッチングする工程、及びパターン化された有機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。
- 半導体基板上に有機下層膜を形成する工程、該有機下層膜上に請求項1乃至請求項11のいずれか1項に記載の薄膜形成組成物を塗布し、焼成して薄膜を形成する工程、該薄膜上に有機レジスト下層膜形成組成物を塗布して有機レジスト下層膜を形成する工程、該有機レジスト下層膜上にレジスト用組成物を塗布してレジスト膜を形成する工程、該レジスト膜を露光する工程、露光後に該レジスト膜を現像しレジストパターンを得る工程、該レジストパターンにより有機レジスト下層膜をエッチングする工程、パターン化された有機レジスト下層膜により薄膜をエッチングする工程、パターン化された薄膜により有機下層膜をエッチングする工程、及びパターン化された有機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。
- 基板上にレジストパターンを形成する工程、その上に請求項1乃至請求項11のいずれか1項に記載の薄膜形成組成物を塗布し、焼成して薄膜を形成する工程、該薄膜をエッチングしてレジスト表面を露出する工程、レジストパターンをエッチングしパターンを反転させる工程を含む半導体装置の製造方法。
- レジストがEUVレジストである請求項13乃至請求項16のいずれか1項に記載の製造方法。
- 半導体基板上にEUVレジスト用組成物を塗布し、焼成してEUVレジスト膜を形成する工程、該EUVレジスト膜上に請求項1乃至請求項11のいずれか1項に記載の薄膜形成組成物を塗布して薄膜を形成する工程、EUVで露光する工程、露光後にEUVレジストを現像しレジストパターンを得る工程、レジストパターン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。
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Also Published As
Publication number | Publication date |
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JP5999372B2 (ja) | 2016-09-28 |
KR101964072B1 (ko) | 2019-04-01 |
CN103718111A (zh) | 2014-04-09 |
KR20140037889A (ko) | 2014-03-27 |
TW201316127A (zh) | 2013-04-16 |
EP2735904A1 (en) | 2014-05-28 |
US20140120730A1 (en) | 2014-05-01 |
EP2735904A4 (en) | 2014-11-26 |
TWI547764B (zh) | 2016-09-01 |
US9093279B2 (en) | 2015-07-28 |
CN103718111B (zh) | 2017-06-23 |
JPWO2013012068A1 (ja) | 2015-02-23 |
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