WO2023008149A1 - レジスト下層膜形成用組成物、半導体基板の製造方法及びレジスト下層膜の形成方法 - Google Patents
レジスト下層膜形成用組成物、半導体基板の製造方法及びレジスト下層膜の形成方法 Download PDFInfo
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- WO2023008149A1 WO2023008149A1 PCT/JP2022/027130 JP2022027130W WO2023008149A1 WO 2023008149 A1 WO2023008149 A1 WO 2023008149A1 JP 2022027130 W JP2022027130 W JP 2022027130W WO 2023008149 A1 WO2023008149 A1 WO 2023008149A1
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- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
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- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
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- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical compound O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical compound CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- MKTNPKQGOBDAPX-UHFFFAOYSA-N naphthalene-2,3,6-triol Chemical compound C1=C(O)C(O)=CC2=CC(O)=CC=C21 MKTNPKQGOBDAPX-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 229920006120 non-fluorinated polymer Polymers 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- HJFRLXPEVRXBQZ-UHFFFAOYSA-N pent-3-yn-2-ol Chemical compound CC#CC(C)O HJFRLXPEVRXBQZ-UHFFFAOYSA-N 0.000 description 1
- WQIQNKQYEUMPBM-UHFFFAOYSA-N pentamethylcyclopentadiene Chemical compound CC1C(C)=C(C)C(C)=C1C WQIQNKQYEUMPBM-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CCTFOFUMSKSGRK-UHFFFAOYSA-N propan-2-olate;tin(4+) Chemical compound [Sn+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] CCTFOFUMSKSGRK-UHFFFAOYSA-N 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 125000005581 pyrene group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGDSVONAYZTTDA-UHFFFAOYSA-N tert-butylphosphonic acid Chemical compound CC(C)(C)P(O)(O)=O OGDSVONAYZTTDA-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- OVZUSPADPSOQQN-UHFFFAOYSA-N tri(propan-2-yloxy)indigane Chemical compound [In+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] OVZUSPADPSOQQN-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
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HKIRVJCLEHCVAL-UHFFFAOYSA-N zinc;propan-2-olate Chemical compound CC(C)O[Zn]OC(C)C HKIRVJCLEHCVAL-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Images
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- G—PHYSICS
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- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- 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
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
Definitions
- the present invention relates to a composition for forming a resist underlayer film, a method for manufacturing a semiconductor substrate, and a method for forming a resist underlayer film.
- a metal hard mask composition which is a resist underlayer film, has been proposed in the manufacture of semiconductor substrates and the like (see Japanese Patent Laid-Open No. 2013-185155).
- a clean track is generally used when manufacturing a semiconductor substrate or the like.
- the clean track is a device that can consistently perform processing steps such as spin coating, EBR (Edge Bead Removal), back rinse, and baking.
- the EBR process is a process of forming a film on a substrate (wafer) by spin coating and then removing the film from the edge portion (peripheral portion) of the substrate with a remover. As a result, contamination of the substrate transfer arm of the clean track can be prevented. Contamination of the transfer arm can cause defects and reduce device manufacturing yield.
- the composition for forming a resist underlayer film has excellent wafer edge removability of the resist underlayer film in the EBR process (remaining part and removed part of the metal hard mask), as well as uniform coatability on the substrate surface. (smoothness of the boundary between the film and the film) and film thickness change (hump) controllability are required.
- the present invention has been made based on the above circumstances, and an object of the present invention is to provide a composition for forming a resist underlayer film which is excellent in all of coatability, wafer edge removability during EBR process, and hump suppression, and An object of the present invention is to provide a method for manufacturing a semiconductor substrate using this and a method for forming a resist underlayer film.
- the present invention in one embodiment, a metal compound (hereinafter also referred to as “[A] compound”); A first structural unit represented by the following formula (1) (hereinafter also referred to as “structural unit (I)”) and a second structural unit represented by the following formula (2) (hereinafter referred to as “structural unit (II) "Also referred to as.) (hereinafter also referred to as “[B] polymer”) and The present invention relates to a composition for forming a resist underlayer film containing a solvent (hereinafter also referred to as "[C] solvent”).
- R 1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- R 2 is a substituted or unsubstituted 1 to 20 carbon atoms). is a valent hydrocarbon group.
- R 3 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- L is a single bond or a divalent linking group.
- Ar is , a group obtained by removing (n+1) hydrogen atoms from a substituted or unsubstituted aromatic ring having 6 to 20 ring members, and R 4 is a monovalent hydroxyalkyl group having 1 to 10 carbon atoms or a hydroxy group .n is an integer of 0 to 8. When n is 2 or more, multiple R 4 are the same or different.
- the present invention in one embodiment, a step of directly or indirectly coating a substrate with a composition for forming a resist underlayer film; a step of directly or indirectly forming a resist pattern on the resist underlayer film formed by the coating step; forming a pattern in the resist underlayer film by etching using the resist pattern as a mask;
- the composition for forming a resist underlayer film is a metal compound; a polymer having a first structural unit represented by the following formula (1) and a second structural unit represented by the following formula (2);
- the present invention relates to a method for manufacturing a semiconductor substrate containing a solvent.
- R 1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- R 2 is a substituted or unsubstituted 1 to 20 carbon atoms). is a valent hydrocarbon group.
- R 3 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- L is a single bond or a divalent linking group.
- Ar is , a group obtained by removing (n+1) hydrogen atoms from a substituted or unsubstituted aromatic ring having 6 to 20 ring members, and R 4 is a monovalent hydroxyalkyl group having 1 to 10 carbon atoms or a hydroxy group .n is an integer of 0 to 8. When n is 2 or more, multiple R 4 are the same or different.
- a step of directly or indirectly applying a composition for forming a resist underlayer film to a substrate is a metal compound; a polymer having a first structural unit represented by the following formula (1) and a second structural unit represented by the following formula (2); and a solvent; It relates to a method for forming a resist underlayer film containing (In formula (1), R 1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms. R 2 is a substituted or unsubstituted 1 to 20 carbon atoms).
- R 3 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- L is a single bond or a divalent linking group.
- Ar is , a group obtained by removing (n+1) hydrogen atoms from a substituted or unsubstituted aromatic ring having 6 to 20 ring members, and R 4 is a monovalent hydroxyalkyl group having 1 to 10 carbon atoms or a hydroxy group .n is an integer of 0 to 8. When n is 2 or more, multiple R 4 are the same or different.
- the composition for forming a resist underlayer film is excellent in all of coatability, wafer edge removability during the EBR process, and hump suppression.
- a resist underlayer film is formed using a composition for forming a resist underlayer film that is excellent in all of coatability, wafer edge removability during an EBR process, and hump suppression, so that a high-quality semiconductor can be obtained. Substrates can be efficiently manufactured.
- a composition for forming a resist underlayer film that is excellent in all of coatability, wafer edge removability during the EBR process, and hump suppression property is used. can be formed into Therefore, these can be suitably used for the manufacture of semiconductor devices, etc., which are expected to be further miniaturized in the future.
- composition for forming a resist underlayer film the method for manufacturing a semiconductor substrate, and the method for forming a resist underlayer film according to each embodiment of the present invention will be described in detail.
- the description of the composition for forming a resist underlayer film will be expanded as appropriate during the description of the method for manufacturing a semiconductor substrate. Combinations of preferred aspects of the embodiments are also preferred.
- the method for manufacturing the semiconductor substrate includes a step of directly or indirectly coating the substrate with the composition for forming a resist underlayer film (hereinafter also referred to as the "composition”) (hereinafter also referred to as the “coating step”). ), a step of forming a resist pattern directly or indirectly on the resist underlayer film formed by the coating step (hereinafter also referred to as a “resist pattern forming step”), and etching using the resist pattern as a mask. and a step of forming a pattern in the resist underlayer film (hereinafter also referred to as an “etching step”).
- a resist underlayer film is formed using a composition for forming a resist underlayer film that is excellent in all of coatability, wafer edge removability during the EBR process, and hump suppression property, so that the resist underlayer film is of high quality. of semiconductor substrates can be efficiently manufactured.
- an organic underlayer film is formed directly or indirectly on the substrate having the resist underlayer film formed by the coating step.
- a step (hereinafter also referred to as an “organic underlayer film forming step”) may be further included.
- a silicon-containing film is formed, if necessary, directly or indirectly on the substrate having the resist underlayer film formed by the coating step, before the resist pattern forming step.
- a step (hereinafter also referred to as a “silicon-containing film forming step”) may be further included.
- composition for forming a resist underlayer film used in the method for manufacturing the semiconductor substrate and the optional steps of forming an organic underlayer film and forming a silicon-containing film are described below.
- composition for forming a resist underlayer film contains [A] compound, [B] polymer and [C] solvent.
- the composition may contain other optional components as long as the effects of the present invention are not impaired.
- a compound refers to a compound containing a metal atom and an oxygen atom.
- metal atoms constituting the compound include metal atoms of Groups 3 to 16 of the periodic table (excluding silicon atoms).
- the compound may have one or more metal atoms.
- Group 3 metal atoms include, for example, scandium, yttrium, lanthanum, cerium, etc.
- Examples of Group 4 metal atoms include titanium, zirconium, hafnium, etc.
- Examples of Group 5 metal atoms include vanadium, niobium, tantalum, etc.
- Examples of Group 6 metal atoms include chromium, molybdenum, tungsten, etc.
- Group 7 metal atoms include manganese, rhenium, etc.
- Group 8 metal atoms include iron, ruthenium, osmium, etc.
- Group 9 metal atoms include cobalt, rhodium, iridium, etc.
- Examples of Group 10 metal atoms include nickel, palladium, platinum, etc.
- Examples of group 11 metal atoms include copper, silver, gold, etc.
- Group 12 metal atoms include zinc, cadmium, mercury, etc.
- Examples of group 13 metal atoms include aluminum, gallium, indium, etc.
- Group 14 metal atoms include germanium, tin, lead, etc.
- Examples of group 15 metal atoms include antimony, bismuth, etc.
- Examples of Group 16 metal atoms include tellurium and the like.
- the metal atoms constituting the above [A] compound are preferably metal atoms of Groups 3 to 16, more preferably metal atoms of Groups 4 to 14, and Groups 4, 5 and 14. Group metal atoms are more preferred, and Group 4 metal atoms are particularly preferred. Specifically, titanium, zirconium, hafnium, tantalum, tungsten, tin, or combinations thereof are more preferable.
- Components other than metal atoms constituting the above [A] compound include organic acids (hereinafter also referred to as “[a] organic acids”), hydroxy acid esters, and ⁇ -diketones. , ⁇ , ⁇ -dicarboxylic acid esters and amine compounds are preferred.
- organic acid refers to an organic compound exhibiting acidity
- organic compound refers to a compound having at least one carbon atom.
- organic acids include carboxylic acids, sulfonic acids, sulfinic acids, organic phosphinic acids, organic phosphonic acids, phenols, enols, thiols, acid imides, oximes, and sulfonamides.
- carboxylic acid examples include formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, 2-ethylhexanoic acid, oleic acid, acrylic acid, and methacrylic acid.
- trans-2,3-dimethylacrylic acid stearic acid, linoleic acid, linolenic acid, arachidonic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, pentafluoropropion Monocarboxylic acids such as acid, gallic acid, shikimic acid, etc., and dicarboxylic acids such as oxalic acid, malonic acid, maleic acid, methylmalonic acid, fumaric acid, adipic acid, sebacic acid, phthalic acid, tartaric acid, etc. and carboxylic acids having 3 or more carboxyl groups such as citric acid.
- sulfonic acid examples include benzenesulfonic acid and p-toluenesulfonic acid.
- sulfinic acid examples include benzenesulfinic acid and p-toluenesulfinic acid.
- organic phosphinic acid examples include diethylphosphinic acid, methylphenylphosphinic acid, and diphenylphosphinic acid.
- organic phosphonic acid examples include methylphosphonic acid, ethylphosphonic acid, t-butylphosphonic acid, cyclohexylphosphonic acid, and phenylphosphonic acid.
- phenols examples include monohydric phenols such as phenol, cresol, 2,6-xylenol, and naphthol; Dihydric phenols such as catechol, resorcinol, hydroquinone, 1,2-naphthalenediol; Trivalent or higher phenols such as pyrogallol and 2,3,6-naphthalenetriol can be mentioned.
- monohydric phenols such as phenol, cresol, 2,6-xylenol, and naphthol
- Dihydric phenols such as catechol, resorcinol, hydroquinone, 1,2-naphthalenediol
- Trivalent or higher phenols such as pyrogallol and 2,3,6-naphthalenetriol can be mentioned.
- Examples of the enol include 2-hydroxy-3-methyl-2-butene, 3-hydroxy-4-methyl-3-hexene, and the like.
- thiols examples include mercaptoethanol and mercaptopropanol.
- the acid imide examples include carboxylic acid imides such as maleimide and succinimide, and sulfonic acid imides such as di(trifluoromethanesulfonic acid)imide and di(pentafluoroethanesulfonic acid)imide. be able to.
- oxime examples include aldoxime such as benzaldoxime and salicylaldoxime, and ketoxime such as diethylketoxime, methylethylketoxime and cyclohexanone oxime.
- aldoxime such as benzaldoxime and salicylaldoxime
- ketoxime such as diethylketoxime, methylethylketoxime and cyclohexanone oxime.
- sulfonamide examples include methylsulfonamide, ethylsulfonamide, benzenesulfonamide, and toluenesulfonamide.
- carboxylic acid is preferable, monocarboxylic acid is more preferable, and methacrylic acid and benzoic acid are more preferable.
- hydroxy acid ester examples include glycolic acid ester, lactic acid ester, 2-hydroxycyclohexane-1-carboxylic acid ester, salicylic acid ester, and the like.
- Examples of the ⁇ -diketone include 2,4-pentanedione, 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, and the like.
- ⁇ -ketoester examples include acetoacetate, ⁇ -alkyl-substituted acetoacetate, ⁇ -ketopentanoate, benzoylacetate, and 1,3-acetonedicarboxylate.
- Examples of amine compounds include diethanolamine and triethanolamine.
- the compound [A] is preferably a metal compound composed of a metal atom and [a] an organic acid, and a metal compound composed of a metal atom of Groups 4, 5 and 14 and a carboxylic acid is More preferred are metal compounds composed of titanium, zirconium, hafnium, tantalum, tungsten or tin and methacrylic acid or benzoic acid.
- the [A] compound may contain one or more of the above metal compounds.
- the [A] compound may contain one or more [a] organic acids.
- the lower limit of the content of the [A] compound in all components contained in the composition is preferably 2% by mass, more preferably 4% by mass, and even more preferably 6% by mass.
- the upper limit of the content ratio is preferably 30% by mass, more preferably 20% by mass, and even more preferably 15% by mass.
- the [A] compound can be synthesized, for example, by [b] a method of performing a hydrolytic condensation reaction using a metal-containing compound, [b] a method of performing a ligand exchange reaction using a metal-containing compound, and the like.
- the "hydrolytic condensation reaction” means that [b] the hydrolyzable group of the metal-containing compound is hydrolyzed and converted to -OH, and the resulting two -OH are dehydrated and condensed to -O- refers to the reaction in which is formed.
- the metal-containing compound includes a metal compound (b1) having a hydrolyzable group, a hydrolyzate of the metal compound (b1) having a hydrolyzable group, and a hydrolyzate of the metal compound (b1) having a hydrolyzable group. condensates or combinations thereof.
- the metal compound (b1) can be used singly or in combination of two or more.
- hydrolyzable group examples include halogen atoms, alkoxy groups, acyloxy groups, and the like.
- halogen atom examples include fluorine atom, chlorine atom, bromine atom, and iodine atom.
- alkoxy group examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group and the like.
- acyloxy group examples include an acetoxy group, an ethylyloxy group, a propionyloxy group, a butyryloxy group, a t-butyryloxy group, a t-amylyloxy group, an n-hexanecarbonyloxy group, and an n-octanecarbonyloxy group.
- an alkoxy group and an acyloxy group are preferable, and an isopropoxy group and an acetoxy group are more preferable.
- the hydrolytic condensate of the metal compound (b1) contains a hydrolyzable group as long as the effects of the present invention are not impaired. It may be a hydrolytic condensate of a metal compound (b1) having a metalloid atom and a compound containing a metalloid atom. That is, the hydrolytic condensate of the metal compound (b1) may contain metalloid atoms within a range that does not impair the effects of the present invention. Examples of the metalloid atoms include silicon, boron, germanium, antimony, and tellurium.
- the content of metalloid atoms in the hydrolytic condensate of the metal compound (b1) is usually less than 50 atomic % with respect to the total of metal atoms and metalloid atoms in the hydrolytic condensate.
- the upper limit of the metalloid atom content is preferably 30 atomic %, more preferably 10 atomic %, relative to the sum of the metal atoms and metalloid atoms in the hydrolyzed condensate.
- Examples of the metal compound (b1) include compounds represented by the following formula ( ⁇ ) (hereinafter also referred to as "[m] compounds").
- M is a metal atom.
- L is a ligand.
- a is an integer from 0 to 2; When a is 2, multiple Ls may be the same or different.
- Y is a hydrolyzable group selected from halogen atoms, alkoxy groups and acyloxy groups.
- b is an integer from 2 to 6; Multiple Y's may be the same or different. Note that L is a ligand that does not correspond to Y.
- Examples of the metal atom represented by M include the same metal atoms as those exemplified as the metal atoms constituting the metal compound contained in the [A] compound.
- ligand represented by L monodentate ligands and polydentate ligands can be mentioned.
- Examples of the monodentate ligand include hydroxo ligands, carboxyl ligands, amide ligands, and ammonia.
- amide ligand examples include unsubstituted amide ligand (NH 2 ), methylamide ligand (NHMe), dimethylamide ligand (NMe 2 ), diethylamide ligand (NEt 2 ), dipropyl An amide ligand (NPr 2 ) and the like can be mentioned.
- polydentate ligand examples include hydroxy acid esters, ⁇ -diketones, ⁇ -ketoesters, ⁇ -dicarboxylic acid esters, hydrocarbons having ⁇ bonds, and diphosphines.
- hydroxy acid ester examples include glycolic acid ester, lactic acid ester, 2-hydroxycyclohexane-1-carboxylic acid ester, salicylic acid ester, and the like.
- Examples of the ⁇ -diketone include 2,4-pentanedione, 3-methyl-2,4-pentanedione, 3-ethyl-2,4-pentanedione, and the like.
- ⁇ -ketoester examples include acetoacetate, ⁇ -alkyl-substituted acetoacetate, ⁇ -ketopentanoate, benzoylacetate, and 1,3-acetonedicarboxylate.
- ⁇ -dicarboxylic acid esters examples include malonic acid diesters, ⁇ -alkyl-substituted malonic acid diesters, ⁇ -cycloalkyl-substituted malonic acid diesters, and ⁇ -aryl-substituted malonic acid diesters.
- hydrocarbons having a ⁇ bond examples include: Chain olefins such as ethylene and propylene; Cyclic olefins such as cyclopentene, cyclohexene, norbornene; Chain dienes such as butadiene and isoprene; Cyclic dienes such as cyclopentadiene, methylcyclopentadiene, pentamethylcyclopentadiene, cyclohexadiene and norbornadiene; Aromatic hydrocarbons such as benzene, toluene, xylene, hexamethylbenzene, naphthalene and indene can be used.
- Chain olefins such as ethylene and propylene
- Cyclic olefins such as cyclopentene, cyclohexene, norbornene
- Chain dienes such as butadiene and isoprene
- Cyclic dienes such as cyclopentadiene, methyl
- diphosphines examples include 1,1-bis(diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 2,2′-bis( diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene and the like.
- halogen atom represented by Y for example, fluorine atom, chlorine atom, bromine atom, iodine atom and the like can be mentioned.
- Examples of the alkoxy group represented by Y include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.
- the acyloxy group represented by Y includes, for example, an acetoxy group, an ethylyloxy group, a butyryloxy group, a t-butyryloxy group, a t-amylyloxy group, an n-hexanecarbonyloxy group, an n-octanecarbonyloxy group, and the like. can be done.
- Y is preferably an alkoxy group or an acyloxy group, more preferably an isopropoxy group or an acetoxy group.
- b is preferably 3 or 4, more preferably 4.
- metal-containing compound a metal alkoxide that is neither hydrolyzed nor hydrolytically condensed, and a metal acyloxide that is neither hydrolyzed nor hydrolytically condensed are preferable.
- Metal-containing compounds include zirconium tetra-n-butoxide, zirconium tetra-n-propoxide, zirconium tetraisopropoxide, hafnium tetraethoxide, indium triisopropoxide, and hafnium tetraisopropoxide.
- hafnium tetra-n-propoxide hafnium tetra-n-butoxide
- tantalum pentaethoxide tantalum penta-n-butoxide
- tungsten pentamethoxide tungsten penta-n-butoxide
- tungsten hexaethoxide tungsten Hexa-n-butoxide
- iron chloride zinc diisopropoxide, zinc acetate dihydrate, tetrabutyl orthotitanate
- titanium tri-n-butoxide stearate bis(cyclopentadienyl)hafnium dichloride, bis(cyclopentadienyl)tungsten dichloride, diacetato [(S)-(-)- 2,2′-bis(dip
- metal alkoxides and metal acyloxides are preferred, metal alkoxides are more preferred, and alkoxides of titanium, zirconium, hafnium, tantalum, tungsten and tin are more preferred.
- the lower limit of the amount of the organic acid used is preferably 1 mol, more preferably 2 mol, per 1 mol of the [b] metal-containing compound.
- the upper limit of the amount of the organic acid used is preferably 6 mol, more preferably 5 mol, per 1 mol of the metal-containing compound [b].
- a compound that can be a multidentate ligand represented by L in the compound of the above formula ( ⁇ ) and a bridging ligand A compound or the like that can become a ligand may be added.
- the compound that can be the bridging ligand include compounds having a plurality of hydroxy groups, isocyanate groups, amino groups, ester groups and amide groups.
- Examples of the [b] method of performing a hydrolysis-condensation reaction using a metal-containing compound include a method of subjecting a [b] metal-containing compound to a hydrolysis-condensation reaction in a solvent containing water. In this case, other compounds having hydrolyzable groups may be added as necessary.
- the lower limit of the amount of water used in this hydrolytic condensation reaction is preferably 0.2-fold mol, more preferably 1-fold mol, and 3-fold mol relative to the hydrolyzable group of the [b] metal-containing compound or the like. More preferred.
- the upper limit of the amount of water is preferably 20-fold mol, more preferably 15-fold mol, and still more preferably 10-fold mol.
- a method of performing a ligand exchange reaction using a metal-containing compound for example, a method of mixing [b] a metal-containing compound and [a] an organic acid can be mentioned.
- the mixture may be mixed in a solvent or may be mixed without using a solvent.
- a base such as triethylamine may be added as necessary.
- the amount of the base to be added is, for example, 1 part by mass or more and 200 parts by mass or less with respect to 100 parts by mass of the total amount of the metal-containing compound [b] and the organic acid [a].
- the solvent used in the synthesis reaction of the compound (hereinafter also referred to as "[d] solvent”) is not particularly limited, and for example, the same solvents as those exemplified as the [C] solvent described later can be used. can.
- alcohol solvents, ether solvents, ester solvents and hydrocarbon solvents are preferred, alcohol solvents, ether solvents and ester solvents are more preferred, monoalcohol solvents and polyhydric alcohol partial ether solvents are preferred.
- Solvents and polyhydric alcohol partial ether carboxylate solvents are more preferred, with ethanol, n-propanol, isopropanol, 1-butanol, propylene glycol monoethyl ether and propylene glycol monoethyl ether acetate being particularly preferred.
- the polymer has structural units (I) and structural units (II) (excluding structural units corresponding to structural units (II) as structural units (I)).
- the polymer may contain structural units other than structural unit (I) and structural unit (II) (hereinafter also simply referred to as "other structural units").
- the polymer can have one or more structural units.
- Structural unit (I) Structural unit (I) is a structural unit represented by the following formula (1). [B] Since the polymer has the structural unit (I), the fluidity of the composition can be improved, and as a result, the wafer edge removability of the resist underlayer film formed from the composition during the EBR process And the hump suppressing property can be improved.
- R 1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- R 2 is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- hydrocarbon group includes chain hydrocarbon groups, alicyclic hydrocarbon groups and aromatic hydrocarbon groups. Moreover, the “hydrocarbon group” includes a saturated hydrocarbon group and an unsaturated hydrocarbon group.
- chain hydrocarbon group refers to a hydrocarbon group that does not contain a cyclic structure and is composed only of a chain structure, and includes both a straight chain hydrocarbon group and a branched chain hydrocarbon group.
- alicyclic hydrocarbon group refers to a hydrocarbon group that contains only an alicyclic structure as a ring structure and does not contain an aromatic ring structure, and includes monocyclic alicyclic hydrocarbon groups and polycyclic alicyclic It contains both hydrocarbon groups.
- the alicyclic hydrocarbon group does not need to consist only of an alicyclic structure, and may partially contain a chain structure.
- An "aromatic hydrocarbon group” refers to a hydrocarbon group containing an aromatic ring structure as a ring structure.
- the aromatic hydrocarbon group does not need to consist only of an aromatic ring structure, and may partially contain a chain structure or an alicyclic structure.
- Examples of the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms for R 1 or R 2 include an unsubstituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted C 3 to 20 monovalent alicyclic hydrocarbon groups, unsubstituted C6-C20 monovalent aromatic hydrocarbon groups, and the like.
- unsubstituted monovalent chain hydrocarbon groups having 1 to 20 carbon atoms examples include alkyl groups such as methyl group, ethyl group, propyl group, butyl group and pentyl group, ethenyl group, propenyl group, butenyl group and the like.
- Alkynyl groups such as an alkenyl group, an ethynyl group, a propynyl group, and a butynyl group, and the like are included.
- Examples of unsubstituted monovalent alicyclic hydrocarbon groups having 3 to 20 carbon atoms include cycloalkyl groups such as cyclopentyl group and cyclohexyl group; cycloalkenyl groups such as cyclopropenyl group, cyclopentenyl group and cyclohexenyl group; Examples include bridged ring hydrocarbon groups such as norbornyl group and adamantyl group.
- unsubstituted monovalent aromatic hydrocarbon groups having 6 to 20 carbon atoms include aryl groups such as phenyl group and naphthyl group, and aralkyl groups such as benzyl group, phenethyl group and naphthylmethyl group.
- Substituents for R 1 or R 2 include, for example, monovalent chain hydrocarbon groups having 1 to 10 carbon atoms, halogen atoms such as fluorine, chlorine, bromine and iodine atoms, methoxy, ethoxy, propoxy Alkoxy groups such as groups, alkoxycarbonyl groups such as methoxycarbonyl groups and ethoxycarbonyl groups, alkoxycarbonyloxy groups such as methoxycarbonyloxy groups and ethoxycarbonyloxy groups, acyl groups such as formyl groups, acetyl groups, propionyl groups and butyryl groups , a cyano group, a nitro group, a hydroxy group, and the like.
- R 1 is preferably a hydrogen atom or a substituted or unsubstituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- a hydrogen atom or a methyl group is more preferred.
- R 2 is preferably a substituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms, more preferably a fluorine atom-substituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms, and a hexafluoroisopropyl group. , 2,2,2-trifluoroethyl group or 3,3,4,4,5,5,6,6-octafluorohexyl group is more preferred. In this case, it is possible to further improve the wafer edge removability and hump suppressing properties during the EBR process of the resist underlayer film formed from the composition.
- fluorine atom-substituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms means that some or all of the hydrogen atoms in a chain hydrocarbon group are substituted with fluorine atoms. means the base.
- the lower limit of the content of the structural unit (I) in the total structural units constituting the polymer is preferably 10 mol%, more preferably 20 mol%, and even more preferably 30 mol%.
- the upper limit of the content ratio is preferably 90 mol %, more preferably 80 mol %, and even more preferably 70 mol %.
- Structural unit (II) Structural unit (II) is a structural unit represented by the following formula (2).
- R 3 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- L is a single bond or a divalent linking group.
- Ar is a group obtained by removing (n+1) hydrogen atoms from a substituted or unsubstituted 6- to 20-membered aromatic ring.
- R 4 is a monovalent hydroxyalkyl group having 1 to 10 carbon atoms or a hydroxy group.
- n is an integer from 0 to 8; When n is 2 or more, multiple R 4 are the same or different.
- Examples of the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms for R 3 include those exemplified as the unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms for R 1 in formula (1) above. groups similar to and the like.
- Examples of the substituent for R 3 include the same groups as those exemplified as the substituent for R 1 in formula (1) above.
- R 3 is preferably a hydrogen atom or a substituted or unsubstituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms, and is preferably a hydrogen atom or an unsubstituted monovalent chain hydrocarbon group having 1 to 20 carbon atoms. is more preferred, and a hydrogen atom or a methyl group is even more preferred.
- divalent linking group for L examples include a divalent hydrocarbon group having 1 to 10 carbon atoms, -COO-, -CO-, -O-, -CONH-, and the like.
- a single bond is preferable for L.
- unsubstituted aromatic rings having 6 to 20 ring members in Ar examples include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, indene ring and pyrene ring, furan ring, pyrrole ring, thiophene ring and phosphole ring. , pyrazole ring, oxazole ring, isoxazole ring, thiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, and triazine ring. Among these, aromatic hydrocarbon rings are preferred.
- the term "number of ring members" refers to the number of atoms forming a ring, and in the case of a polycyclic ring, the number of atoms forming the polycycle.
- substituent for Ar examples include the same groups as those exemplified as the substituent for R 1 in the above formula (1). However, R4 described later is not regarded as a substituent for Ar.
- Ar is preferably a group obtained by removing (n+1) hydrogen atoms from an unsubstituted 6 to 20 ring-membered aromatic ring, and (n+1) from an unsubstituted 6 to 20 ring-membered aromatic hydrocarbon ring.
- a group in which a hydrogen atom has been removed is more preferred, and a group in which (n+1) hydrogen atoms have been removed from an unsubstituted benzene ring is even more preferred.
- the monovalent hydroxyalkyl group having 1 to 10 carbon atoms for R 4 is a group obtained by substituting some or all of the hydrogen atoms of a monovalent alkyl group having 1 to 10 carbon atoms with hydroxy groups.
- R 4 is preferably a monovalent hydroxyalkyl group having 1 to 10 carbon atoms, more preferably a monovalent monohydroxyalkyl group having 1 to 10 carbon atoms, and even more preferably a monohydroxymethyl group.
- R 4 is the above group, the flatness of the resist underlayer film formed from the composition can be further improved.
- n is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1.
- the lower limit of the content of the structural unit (II) in the total structural units constituting the polymer is preferably 10 mol%, more preferably 20 mol%, and even more preferably 30 mol%.
- the upper limit of the content ratio is preferably 90 mol %, more preferably 80 mol %, and even more preferably 70 mol %.
- Other structural units include, for example, structural units derived from (meth)acrylic acid esters, structural units derived from (meth)acrylic acid, and structural units derived from acenaphthylene compounds.
- the upper limit of the content of the other structural units in the total structural units constituting the [B] polymer is preferably 20 mol%, more preferably 5 mol%. .
- the lower limit of the Mw of the polymer is preferably 1,000, more preferably 2,000, still more preferably 3,000, and particularly preferably 3,500.
- the upper limit of Mw is preferably 100,000, more preferably 50,000, still more preferably 30,000, and particularly preferably 20,000.
- the upper limit of Mw/Mn of the polymer is preferably 5, more preferably 3, and even more preferably 2.5.
- the lower limit of Mw/Mn is usually 1, preferably 1.2.
- the lower limit of the content of the [B] polymer in the composition is preferably 0.00001 parts by mass, more preferably 0.00005 parts by mass, and 0.0001 parts by mass with respect to 10 parts by mass of the [A] compound. is more preferred, and 0.001 part by mass is particularly preferred.
- the upper limit of the content is preferably 2 parts by mass, more preferably 1.5 parts by mass, still more preferably 1 part by mass, and particularly preferably 0.8 parts by mass.
- a monomer that gives the structural unit (I), a monomer that gives the structural unit (II), and, if necessary, a monomer that gives another structural unit are each predetermined. It can be synthesized by using in an amount such that the content ratio of is and polymerizing by a known method.
- the [C] solvent is not particularly limited as long as it can dissolve or disperse at least the [A] compound, [B] polymer and other optional components.
- the composition may contain one or more [C] solvents.
- solvents include organic solvents.
- organic solvents include alcohol solvents, ketone solvents, ether solvents, ester solvents, nitrogen-containing solvents, and the like.
- alcoholic solvents examples include monoalcoholic solvents such as methanol, ethanol, n-propanol, isopropanol and 1-butanol, and polyhydric alcohols such as ethylene glycol, 1,2-propylene glycol, triethylene glycol and tripropylene glycol. system solvents and the like can be mentioned.
- ketone solvents include chain ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and 2-heptanone, and cyclic ketone solvents such as cyclohexanone.
- ether solvents include chain ether solvents such as n-butyl ether, polyhydric alcohol ether solvents such as cyclic ether solvents such as tetrahydrofuran and 1,4-dioxane, propylene glycol monoethyl ether, and tripropylene glycol.
- chain ether solvents such as n-butyl ether
- polyhydric alcohol ether solvents such as cyclic ether solvents such as tetrahydrofuran and 1,4-dioxane
- propylene glycol monoethyl ether propylene glycol monoethyl ether
- tripropylene glycol examples include polyhydric alcohol partial ether solvents such as monomethyl ether and tetraethylene glycol monomethyl ether.
- ester solvents include carbonate solvents such as diethyl carbonate, acetic acid monoester solvents such as methyl acetate, ethyl acetate, and butyl acetate, lactone solvents such as ⁇ -butyrolactone, diethylene glycol monomethyl ether acetate, and propylene glycol monomethyl ether.
- Examples include polyhydric alcohol partial ether carboxylate solvents such as acetate, and lactate ester solvents such as methyl lactate and ethyl lactate.
- nitrogen-containing solvents examples include linear nitrogen-containing solvents such as N,N-dimethylacetamide and cyclic nitrogen-containing solvents such as N-methylpyrrolidone.
- aromatic solvents such as toluene, xylene, and mesitylene can be mentioned.
- the solvent is preferably an ether solvent and/or an ester solvent, more preferably a polyhydric alcohol partial ether solvent and/or a polyhydric alcohol partial ether carboxylate solvent, propylene glycol monoethyl ether and/or Propylene glycol monomethyl ether acetate is more preferred.
- the lower limit of the content of the [C] solvent in the total amount of the [A] compound and [C] solvent is more preferably 50% by mass, preferably 60% by mass, and more preferably 70% by mass.
- the upper limit of the content is preferably 99% by mass, more preferably 95% by mass, and more preferably 90% by mass.
- composition may contain, for example, an acid generator, a polymer additive, a polymerization inhibitor, a surfactant, etc., as components other than those mentioned above.
- the content of the other optional ingredients in the composition can be appropriately determined according to the type and function of the other optional ingredients used.
- An acid generator is a compound that generates an acid upon exposure to radiation and/or heating.
- the composition can contain one or more acid generators.
- acid generators include onium salt compounds and N-sulfonyloxyimide compounds.
- the composition can further improve the coatability of the substrate and the organic underlayer film, as well as the continuity of the film.
- the composition may contain one or more polymeric additives.
- polymer additives examples include (poly)oxyalkylene polymer compounds, fluorine-containing polymer compounds, and non-fluorine polymer compounds.
- Examples of (poly)oxyalkylene-based polymer compounds include polyoxyalkylenes such as (poly)oxyethylene (poly)oxypropylene adducts, diethylene glycol heptyl ether, polyoxyethylene oleyl ether, polyoxypropylene butyl ether, polyoxy Ethylene polyoxypropylene-2-ethylhexyl ether, (poly)oxyalkyl ethers such as oxyethyleneoxypropylene adducts to higher alcohols having 12 to 14 carbon atoms, polyoxypropylene phenyl ether, polyoxyethylene nonylphenyl ether, etc.
- polyoxyalkylenes such as (poly)oxyethylene (poly)oxypropylene adducts, diethylene glycol heptyl ether, polyoxyethylene oleyl ether, polyoxypropylene butyl ether, polyoxy Ethylene polyoxypropylene-2-ethylhexyl ether, (pol
- poly)oxyalkylene(alkyl)aryl ethers 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 2,5-dimethyl-3-hexyne-2,5-diol, 3 -Acetylene ethers obtained by addition polymerization of alkylene oxide to acetylene alcohol such as methyl-1-butyn-3-ol, (poly)oxyalkylene fatty acid esters such as diethylene glycol oleate, diethylene glycol laurate, and ethylene glycol distearate (poly)oxyalkylene sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurate and polyoxyethylene sorbitan trioleate, sodium polyoxypropylene methyl ether sulfate, sodium polyoxyethylene dodecylphenol ether sulfate, etc.
- Oxyalkylene alkyl (aryl) ether sulfate salts, (poly) oxyalkylene alkyl phosphates such as (poly) oxyethylene stearyl phosphate, (poly) oxyalkylene alkyl amines such as polyoxyethylene laurylamine, etc. can give
- fluorine-containing polymer compounds examples include compounds described in JP-A-2011-89090.
- the fluorine-containing polymer compound for example, a repeating unit derived from a (meth)acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably an ethyleneoxy group or a propyleneoxy group). and a repeating unit derived from a (meth)acrylate compound having
- non-fluorinated polymer compounds include lauryl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, isooctyl (meth)acrylate, isostearyl ( meth)acrylates, linear or branched alkyl (meth)acrylates such as isononyl (meth)acrylate, alkoxyethyl (meth)acrylates such as methoxyethyl (meth)acrylate, ethylene glycol di(meth)acrylate, 1,3 - Alkylene glycol di(meth)acrylates such as butylene glycol di(meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl ( Hydroxyalkyl (meth)acrylates such as meth)acrylates, dicyclopen
- the composition can improve the storage stability of the composition by containing a polymerization inhibitor.
- the composition can contain one or more polymerization inhibitors.
- polymerization inhibitors examples include hydroquinone compounds such as 4-methoxyphenol and 2,5-di-tert-butylhydroquinone, and nitroso compounds such as N-nitrosophenylhydroxylamine and aluminum salts thereof.
- the composition can further improve the coatability of the substrate and the organic underlayer film, as well as the continuity of the film.
- the composition can contain one or more surfactants.
- surfactants examples include “Newcol 2320”, “Newcol 714-F”, “Newcol 723”, “Newcol 2307”, “Newcol 2303” (Nippon Emulsifier Co., Ltd.), “Pionin D -1107-S”, “Pionin D-1007”, “Pionin D-1106-DIR”, “Nucalgen TG310”, “Nucalgen TG310”, “Pionin D-6105-W”, “Pionin D-6112", “Pionin D-6512” (above, Takemoto Oil Co., Ltd.), “Surfinol 420", “Surfinol 440", “Surfinol 465", “Surfinol 2502” (above, Japan Air Products Co., Ltd.), "Megafac F171", “F172”, “F173”, “F176”, “F177”, “F141”, “F142”, “F143”, “F144”, “R30” , "Same F4
- composition for forming a resist underlayer film is prepared by mixing the [A] compound, [B] polymer, [C] solvent and optionally optional components in a predetermined ratio, and preferably the obtained mixture is sieved to have a pore size of 0.5. It can be prepared by filtering with a membrane filter of 5 ⁇ m or less.
- the composition for forming a resist underlayer film is directly or indirectly coated onto the substrate.
- the method of coating the composition for forming a resist underlayer film is not particularly limited, and can be carried out by an appropriate method such as spin coating, casting coating, roll coating, or the like. As a result, a coating film is formed, and [C] a resist underlayer film is formed by volatilization of the solvent.
- the substrate examples include metal or semimetal substrates such as silicon substrates, aluminum substrates, nickel substrates, chromium substrates, molybdenum substrates, tungsten substrates, copper substrates, tantalum substrates, and titanium substrates.
- metal or semimetal substrates such as silicon substrates, aluminum substrates, nickel substrates, chromium substrates, molybdenum substrates, tungsten substrates, copper substrates, tantalum substrates, and titanium substrates.
- silicon substrates are preferred.
- the substrate may be a substrate on which a silicon nitride film, an alumina film, a silicon dioxide film, a tantalum nitride film, a titanium nitride film, or the like is formed.
- the lower limit to the average thickness of the resist underlayer film to be formed is preferably 3 nm, more preferably 5 nm, and even more preferably 10 nm.
- the upper limit of the average thickness is preferably 500 nm, more preferably 200 nm, and even more preferably 50 nm. The method for measuring the average thickness is described in Examples.
- the method for manufacturing the semiconductor substrate preferably further includes a step of heating the coating film formed by the coating step (hereinafter also referred to as a "heating step").
- the heating of the coating promotes the formation of the resist underlayer film. More specifically, heating the coating film promotes volatilization of the [C] solvent.
- the heating of the coating film is usually performed in the air, but may be performed in a nitrogen atmosphere.
- the lower limit of the heating temperature is preferably 150°C, more preferably 200°C.
- the upper limit of the temperature is preferably 600°C, more preferably 400°C.
- the lower limit of the heating time is preferably 15 seconds, more preferably 30 seconds.
- the upper limit of the time is preferably 1,200 seconds, more preferably 600 seconds.
- the organic underlayer film can be formed by coating a composition for forming an organic underlayer film.
- the method of forming the organic underlayer film by coating the composition for forming an organic underlayer film includes, for example, coating the composition for forming an organic underlayer film directly or indirectly on a substrate having the resist underlayer film. A method of curing the coating film by heating or exposing it to light can be mentioned.
- the composition for forming the organic underlayer film for example, "HM8006" manufactured by JSR Corporation can be used. Various conditions for heating and exposure can be appropriately determined according to the type of the organic underlayer film-forming composition to be used.
- Silicon-containing film forming step In this step, prior to the resist pattern forming step, a silicon-containing film is formed directly or indirectly on the substrate having the resist underlayer film formed in the coating step.
- a case of indirectly forming a silicon-containing film on a substrate having the resist underlayer film includes, for example, a case where a surface-modified film of the resist underlayer film is formed on the resist underlayer film.
- a silicon-containing film can be formed by coating a composition for forming a silicon-containing film, chemical vapor deposition (CVD), atomic layer deposition (ALD), or the like.
- CVD chemical vapor deposition
- ALD atomic layer deposition
- a method of forming a silicon-containing film by coating a silicon-containing film-forming composition for example, a coating formed by directly or indirectly coating a silicon-containing film-forming composition on the resist underlayer film.
- a method of curing the coating film by exposure and/or heating can be mentioned.
- Commercially available products of the silicon-containing film-forming composition include, for example, "NFC SOG01", “NFC SOG04", and "NFC SOG080" (manufactured by JSR Corporation).
- Silicon oxide films, silicon nitride films, silicon oxynitride films, and amorphous silicon films can be formed by chemical vapor deposition (CVD) or atomic layer deposition (ALD).
- resist pattern forming step In this step, a resist pattern is formed directly or indirectly on the resist underlayer film.
- the method for carrying out this step include a method using a resist composition, a method using a nanoimprint method, a method using a self-assembled composition, and the like.
- Examples of forming a resist pattern indirectly on the resist underlayer film include, for example, forming a resist pattern on the silicon-containing film in the case where the method for manufacturing the semiconductor substrate includes the step of forming the silicon-containing film. I can give
- the method using the above resist composition includes applying the resist composition so that the resist film to be formed has a predetermined thickness, and then pre-baking to volatilize the solvent in the coating film. to form a resist film.
- the resist composition examples include a positive or negative chemically amplified resist composition containing a radiation-sensitive acid generator, a positive resist composition containing an alkali-soluble resin and a quinonediazide-based photosensitizer, an alkali A negative resist composition containing a soluble resin and a cross-linking agent can be mentioned.
- a commercially available resist composition can be used as it is.
- the radiation used for exposure can be appropriately selected according to the type of radiation-sensitive acid generator used in the resist composition.
- Examples include electromagnetic waves, electron beams, molecular beams, and particle beams such as ion beams.
- far ultraviolet rays are preferred, and KrF excimer laser light (248 nm), ArF excimer laser light (193 nm), F2 excimer laser light (wavelength 157 nm), Kr2 excimer laser light ( wavelength 147 nm), ArKr excimer laser light.
- extreme ultraviolet rays wavelength of 13.5 nm, etc., hereinafter also referred to as "EUV" are more preferred, and KrF excimer laser light, ArF excimer laser light, or EUV is even more preferred.
- post-baking can be performed to improve the resolution, pattern profile, developability, and the like.
- the temperature and time of this post-baking can be appropriately determined according to the type of resist composition used.
- the exposed resist film is developed with a developer to form a resist pattern.
- This development may be either alkali development or organic solvent development.
- As the developer in the case of alkali development, basic aqueous solutions such as ammonia, triethanolamine, tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide and the like can be mentioned. Suitable amounts of water-soluble organic solvents such as alcohols such as methanol and ethanol, surfactants and the like can also be added to these basic aqueous solutions.
- examples of the developer include various organic solvents exemplified as the [C] solvent of the composition.
- a predetermined resist pattern is formed by washing and drying after development with the developer.
- a pattern is formed in the resist underlayer film by etching using the resist pattern as a mask.
- Etching may be performed once or multiple times, that is, etching may be performed sequentially using the pattern obtained by etching as a mask, but multiple times is preferable from the viewpoint of obtaining a pattern with a better shape.
- the silicon-containing film, the organic underlayer film, the resist underlayer film, and the substrate are sequentially etched in this order.
- the etching method dry etching, wet etching, and the like can be mentioned. Among these, dry etching is preferable from the viewpoint of improving the pattern shape of the substrate.
- gas plasma such as oxygen plasma is used.
- a semiconductor substrate having a predetermined pattern is obtained by the etching.
- Dry etching can be performed using, for example, a known dry etching apparatus.
- the etching gas used for dry etching can be appropriately selected depending on the mask pattern, the elemental composition of the film to be etched, etc. Examples include CHF 3 , CF 4 , C 2 F 6 , C 3 F 8 , SF 6 and the like.
- chlorine-based gases such as Cl 2 and BCl 3 ; oxygen-based gases such as O 2 , O 3 and H 2 O; H 2 , NH 3 , CO, CO 2 , CH 4 and C 2 H 2 ; Reducing gases such as C2H4 , C2H6 , C3H4 , C3H6 , C3H8 , HF, HI, HBr , HCl, NO, NH3 , BCl3 , He, N2 , an inert gas such as Ar. These gases can also be mixed and used.
- a fluorine-based gas is usually used.
- the method for forming the resist underlayer film includes a step of directly or indirectly coating a substrate with a composition for forming a resist underlayer film.
- a composition for forming a resist underlayer film the composition for forming a resist underlayer film used in the method for manufacturing a semiconductor substrate can be suitably employed.
- the coating step the coating step in the above method for manufacturing a semiconductor substrate can be suitably employed.
- Concentration of components other than the solvent in the mixture containing the [A] compound in the present embodiment, the weight average molecular weight (Mw) of the hydrolytic condensate in the mixture containing the [A] compound, the weight average molecular weight of the [B] polymer (Mw) and the average thickness of the film were measured by the following method.
- the average thickness of the resist underlayer film is determined by measuring the film thickness at arbitrary 9 points at intervals of 5 cm including the center of the resist underlayer film using a spectroscopic ellipsometer ("M2000D" manufactured by JA WOOLLAM). It was obtained by calculating the average value of the film thickness of .
- x-1 propionic acid
- x-2 butyric acid
- x-3 isobutyric acid
- x-4 methacrylic acid
- x-5 2-ethylhexanoic acid
- x-6 acetylacetone
- x-7 diethanolamine
- the start of dropping was defined as the start time of the polymerization reaction, and after the polymerization reaction was carried out for 6 hours, the mixture was cooled to 30°C or less. 300 g of propylene glycol monomethyl ether acetate was added to the reaction solution, and methyl isobutyl ketone was removed by concentration under reduced pressure to obtain a propylene glycol monomethyl ether acetate solution of polymer (B-1). Mw of the polymer (B-1) was 4,200.
- Mw of polymer (B-2) is 3,800, Mw of polymer (B-3) is 4,000, Mw of polymer (B-4) is 4,300, polymer (B-5) Mw is 4,500, Mw of polymer (B-6) is 4,100, Mw of polymer (B-7) is 4,100, Mw of polymer (B-8) is 4,200, polymer Mw of (B-9) was 4,200, Mw of polymer (B-10) was 4,300, and Mw of polymer (b-1) was 4,100.
- F-1 4-methoxyphenol
- F-2 Surfactant ("NBX-15” of Neos Co., Ltd.)
- F-3 Surfactant (“F563” from DIC Corporation)
- composition (J-1) Preparation of composition (J-1) As shown in Table 2 below, [A] compound (A-1) 10 parts by mass, [B] polymer (B-1) was mixed so that 0.05 parts by mass and 90 parts by mass of (C-3) as the [C] solvent. The resulting solution was filtered through a polytetrafluoroethylene (PTFE) filter with a pore size of 0.2 ⁇ m to prepare composition (J-1). "-" in the [B] polymer and [F] other optional components in Table 2 below indicates that the [B] polymer and [F] other optional components were not used. The same applies hereinafter.
- PTFE polytetrafluoroethylene
- composition (J-2) As shown in Table 2 below, [A] a mixture containing compound (A-2) and [C] (C-1) as a solvent , With respect to 10 parts by mass of components other than the solvent in the [A] compound (A-2), the [B] polymer (B-1) is 0.05 parts by mass, and the [C] solvent is 90 parts by mass ([ A] was mixed so that the [C] solvent is also included in the mixture containing the compound). The resulting solution was filtered through a polytetrafluoroethylene (PTFE) filter with a pore size of 0.2 ⁇ m to prepare composition (J-2).
- PTFE polytetrafluoroethylene
- compositions (J-3) to (J-38) were prepared in the same manner as in Example 1-2.
- compositions (j-1) to (j-4) Example 1-2 Preparation of compositions (j-1) to (j-4) Example 1-2 except that the types and contents of each component were as shown in Table 2 below Compositions (j-1) to (j-4) were prepared in the same manner.
- FIG. 1A is an optical microscope photograph when no uneven removal was observed in the evaluation of wafer edge removability
- FIG. 1B is an optical microscope photograph when uneven removal was observed in the evaluation of wafer edge removability.
- the height change at the position from the outer peripheral edge of the substrate with the resist underlayer film to the center of the substrate up to 10 mm in length was measured with a stylus type step meter (KLA Alpha-Step D-600, stylus pressure 5 mg).
- KLA Alpha-Step D-600 stylus pressure 5 mg.
- compositions of Examples and the resist underlayer films formed from the compositions were superior to Comparative Examples in coatability, wafer edge removability, and hump suppression.
- the composition for forming a resist underlayer film of the present invention is excellent in all of coatability, wafer edge removability during EBR process, and hump suppression property.
- a resist underlayer film is formed using a composition for forming a resist underlayer film that is excellent in all of coatability, wafer edge removability during EBR process, and hump suppression property, so that the resist underlayer film is of high quality. of semiconductor substrates can be efficiently manufactured.
- a composition for forming a resist underlayer film that is excellent in all of coatability, wafer edge removability during EBR process, and hump suppression property is used, so that a desired resist underlayer film can be formed. It can be formed efficiently. Therefore, these can be suitably used for the manufacture of semiconductor devices, etc., which are expected to be further miniaturized in the future.
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Abstract
Description
金属化合物(以下、「[A]化合物」ともいう。)と、
下記式(1)で表される第1構造単位(以下、「構造単位(I)」ともいう。)及び下記式(2)で表される第2構造単位(以下、「構造単位(II)」ともいう。)を有する重合体(以下、「[B]重合体」ともいう。)と、
溶媒(以下、「[C]溶媒」ともいう。)と
を含有する、レジスト下層膜形成用組成物に関する。
基板に、直接又は間接に、レジスト下層膜形成用組成物を塗工する工程と、
上記塗工工程により形成されたレジスト下層膜に、直接又は間接に、レジストパターンを形成する工程と、
上記レジストパターンをマスクとしたエッチングにより上記レジスト下層膜にパターンを形成する工程と
を含み、
上記レジスト下層膜形成用組成物が、
金属化合物と、
下記式(1)で表される第1構造単位及び下記式(2)で表される第2構造単位を有する重合体と、
溶媒と
を含有する、半導体基板の製造方法に関する。
基板に直接又は間接にレジスト下層膜形成用組成物を塗工する工程
を備え、
上記レジスト下層膜形成用組成物が、
金属化合物と、
下記式(1)で表される第1構造単位及び下記式(2)で表される第2構造単位を有する重合体と
溶媒と、
を含有する、レジスト下層膜の形成方法に関する。
当該半導体基板の製造方法は、基板に、直接又は間接に、当該レジスト下層膜形成用組成物(以下、「組成物」ともいう。)を塗工する工程(以下、「塗工工程」ともいう)と、上記塗工工程により形成されたレジスト下層膜に、直接又は間接に、レジストパターンを形成する工程(以下、「レジストパターン形成工程」ともいう)と、上記レジストパターンをマスクとしたエッチングにより上記レジスト下層膜にパターンを形成する工程(以下、「エッチング工程」ともいう)とを含む。
当該レジスト下層膜形成用組成物(以下、単に「組成物」ともいう。)は、[A]化合物、[B]重合体及び[C]溶媒を含有する。当該組成物は、本発明の効果を損なわない範囲において、その他の任意成分を含有していてもよい。
[A]化合物は、金属原子と酸素原子とを含む化合物をいう。[A]化合物を構成する金属原子としては、例えば、周期表第3族~第16族の金属原子(但し、ケイ素原子を除く)等をあげることができる。[A]化合物は、1種又は2種以上の金属原子を有していてもよい。
第4族の金属原子としては、例えば、チタン、ジルコニウム、ハフニウム等が、
第5族の金属原子としては、例えば、バナジウム、ニオブ、タンタル等が、
第6族の金属原子としては、例えば、クロム、モリブデン、タングステン等が、
第7族の金属原子としては、マンガン、レニウム等が、
第8族の金属原子としては、鉄、ルテニウム、オスミウム等が、
第9族の金属原子としては、コバルト、ロジウム、イリジウム等が、
第10族の金属原子としては、ニッケル、パラジウム、白金等が、
第11族の金属原子としては、銅、銀、金等が、
第12族の金属原子としては、亜鉛、カドミウム、水銀等が、
第13族の金属原子としては、アルミニウム、ガリウム、インジウム等が、
第14族の金属原子としては、ゲルマニウム、スズ、鉛等が、
第15族の金属原子としては、アンチモン、ビスマス等が、
第16族の金属原子としては、テルル等をあげることができる。
カテコール、レゾルシノール、ハイドロキノン、1,2-ナフタレンジオール等の2価のフェノール類;
ピロガロール、2,3,6-ナフタレントリオール等の3価以上のフェノール類等をあげることができる。
[A]化合物は、例えば、[b]金属含有化合物を用いて加水分解縮合反応を行う方法、[b]金属含有化合物を用いて配位子交換反応を行う方法等により合成することができる。ここで「加水分解縮合反応」とは、[b]金属含有化合物が有する加水分解性基が加水分解して-OHに変換され、得られた2個の-OHが脱水縮合して-O-が形成される反応をいう。
[b]金属含有化合物は、加水分解性基を有する金属化合物(b1)、加水分解性基を有する金属化合物(b1)の加水分解物、加水分解性基を有する金属化合物(b1)の加水分解縮合物又はこれらの組み合わせである。金属化合物(b1)は、1種単独で又は2種以上組み合わせて使用できる。
エチレン、プロピレン等の鎖状オレフィン;
シクロペンテン、シクロヘキセン、ノルボルネン等の環状オレフィン;
ブタジエン、イソプレン等の鎖状ジエン;
シクロペンタジエン、メチルシクロペンタジエン、ペンタメチルシクロペンタジエン、シクロヘキサジエン、ノルボルナジエン等の環状ジエン;
ベンゼン、トルエン、キシレン、ヘキサメチルベンゼン、ナフタレン、インデン等の芳香族炭化水素等をあげることができる。
[B]重合体は、構造単位(I)及び構造単位(II)を有する(ただし、構造単位(I)として構造単位(II)に該当する構造単位を除く。)。[B]重合体は、構造単位(I)及び構造単位(II)以外のその他の構造単位(以下、単に「その他の構造単位」ともいう)を含有していてもよい。[B]重合体は、1種又は2種以上の各構造単位を有することができる。
構造単位(I)は、下記式(1)で表される構造単位である。[B]重合体が構造単位(I)を有することにより、当該組成物の流動性を向上させることができ、その結果、当該組成物により形成されるレジスト下層膜のEBR工程時のウエハエッジ除去性及びハンプ抑制性を向上させることができる。
構造単位(II)は、下記式(2)で表される構造単位である。[B]重合体が構造単位(II)を有することにより、[A]化合物との相溶性及び基板との親和性を向上させることができ、その結果、当該組成物の塗工性を向上させることができる。
その他の構造単位としては、例えば(メタ)アクリル酸エステルに由来する構造単位、(メタ)アクリル酸に由来する構造単位、アセナフチレン化合物に由来する構造単位等が挙げられる。
[B]重合体は、例えば構造単位(I)を与える単量体と、構造単位(II)を与える単量体と、必要に応じてその他の構造単位を与える単量体とを、それぞれ所定の含有割合となるような使用量で用い、公知の方法により重合させることによって合成することができる。
[C]溶媒としては、少なくとも[A]化合物、[B]重合体及びその他の任意成分等を溶解又は分散可能な溶媒であれば特に限定されない。当該組成物は、1種又は2種以上の[C]溶媒を含有することができる。
当該組成物は、上記したもの以外の他の成分として、例えば、酸発生剤、高分子添加剤、重合禁止剤、界面活性剤等を含有していてもよい。
当該レジスト下層膜形成用組成物は、[A]化合物、[B]重合体、[C]溶媒及び必要に応じて任意成分を所定の割合で混合し、好ましくは得られた混合物を孔径0.5μm以下のメンブランフィルター等でろ過することにより調製できる。
塗工工程では、基板に、直接又は間接に、当該レジスト下層膜形成用組成物を塗工する。レジスト下層膜形成用組成物の塗工方法としては特に限定されず、例えば回転塗工、流延塗工、ロール塗工などの適宜の方法で実施することができる。これにより塗工膜が形成され、[C]溶媒の揮発などが起こることによりレジスト下層膜が形成される。
本工程では、上記レジストパターン形成工程より前に、上記塗工工程により形成された当該レジスト下層膜を有する基板に、直接又は間接に、有機下層膜を形成する。
本工程では、上記レジストパターン形成工程より前に、上記塗工工程により形成された当該レジスト下層膜を有する基板に、直接又は間接に、ケイ素含有膜を形成する。
本工程では、当該レジスト下層膜に対し、直接又は間接に、レジストパターンを形成する。本工程を行う方法としては、例えば、レジスト組成物を用いる方法、ナノインプリント法を用いる方法、自己組織化組成物を用いる方法等をあげることができる。当該レジスト下層膜に間接にレジストパターンを形成する場合としては、例えば、当該半導体基板の製造方法が上記ケイ素含有膜形成工程を含む場合において、上記ケイ素含有膜上にレジストパターンを形成する場合等をあげることができる。
本工程では、上記レジストパターンをマスクとしたエッチングにより上記レジスト下層膜にパターンを形成する。エッチングの回数としては1回でも、複数回、すなわちエッチングにより得られるパターンをマスクとして順次エッチングを行ってもよいが、より良好な形状のパターンを得る観点からは、複数回が好ましい。複数回のエッチングを行う場合、ケイ素含有膜、有機下層膜、レジスト下層膜及び基板の順に順次エッチングを行う。エッチングの方法としては、ドライエッチング、ウエットエッチング等をあげることができる。これらの中で、基板のパターンの形状をより良好なものとする観点から、ドライエッチングが好ましい。このドライエッチングには、例えば、酸素プラズマ等のガスプラズマ等が用いられる。上記エッチングにより、所定のパターンを有する半導体基板が得られる。
当該レジスト下層膜の形成方法は、基板に直接又は間接にレジスト下層膜形成用組成物を塗工する工程を備える。レジスト下層膜形成用組成物としては、上記半導体基板の製造方法において用いられるレジスト下層膜形成用組成物を好適に採用することができる。塗工工程としては、上記半導体基板の製造方法における塗工工程を好適に採用することができる。
[A]化合物を含む混合物0.5gを250℃で30分間焼成した後の残渣の質量を測定し、この残渣の質量を[A]化合物を含む混合物の質量で除することにより、[A]化合物を含む混合物中の溶媒以外の成分の濃度(質量%)を算出した。
GPCカラム(東ソー(株)の「AWM-H」2本、「AW-H」1本及び「AW2500」2本)を使用し、流量:0.3mL/分、溶出溶媒:N,N-ジメチルアセトアミドにLiBr(30mM)及びクエン酸(30mM)を添加したもの、カラム温度:40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフィー(検出器:示差屈折計)により測定した。
重合体のMwは、GPCカラム(東ソー(株)の「G2000HXL」2本、「G3000HXL」1本、「G4000HXL」1本)を使用し、流量:1.0mL/分、溶出溶媒:テトラヒドロフラン、カラム温度:40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフィー(検出器:示差屈折計)により測定した。
レジスト下層膜の平均厚みは、分光エリプソメータ(J.A.WOOLLAM社の「M2000D」)を用いて、レジスト下層膜の中心を含む5cm間隔の任意の9点の位置で膜厚を測定し、それらの膜厚の平均値を算出して求めた。
[A]化合物の合成に用いた[m]化合物、[x]化合物、[d]溶媒、及び[C]溶媒を以下に示す。以下の合成例においては特に断りのない限り、「質量部」は使用した[m]化合物の質量を100質量部とした場合の値を意味する。また、「モル比」は使用した[m]化合物の物質量を1とした場合の値を意味する。[A]化合物を含む混合物中の溶媒以外の成分の濃度(質量%)を表1に併せて示す。
m-1:テトラ-n-プロポキシジルコニウム(IV)
m-2:テトラ-n-ブトキシジルコニウム(IV)
m-3:テトラ-n-プロポキシハフニウム(IV)
m-4:テトライソプロポキシチタン(IV)
m-5:ペンタエトキシタンタル(V)
x-1:プロピオン酸
x-2:酪酸
x-3:イソ酪酸
x-4:メタクリル酸
x-5:2-エチルヘキサン酸
x-6:アセチルアセトン
x-7:ジエタノールアミン
d-1:n-プロパノール
d-2:エタノール
d-3:1-ブタノール
d-4:イソプロパノール
C-1:プロピレングリコールモノメチルエーテルアセテート
C-2:プロピレングリコールモノエチルエーテル
窒素雰囲気下、反応容器内において化合物(m-1)、溶媒(d-1)(40質量部)を投入した。上記反応容器において、50℃で攪拌しながら、化合物(x-1)(モル比5)を20分かけて滴下した。次いで、80℃で反応を3時間実施した。反応終了後、反応容器内を30℃以下に冷却した。冷却により得られた沈殿物をろ別し、n-ヘキサン(100質量部)で洗浄したのち、真空乾燥することにより化合物(A-1)を得た。
窒素雰囲気下、反応容器内において化合物(m-1)、溶媒(d-1)(200質量部)を投入した。上記反応容器において、50℃で攪拌しながら、化合物(x-2)(モル比5)を20分かけて滴下した。次いで、80℃で反応を3時間実施した。反応終了後、反応容器内を30℃以下に冷却した。冷却した反応溶液に、溶媒(C-1)900質量部を加えた後、エバポレーターを用いて、溶媒(d-1)、反応により生成したアルコール、及び余剰の溶媒(C-1)を除去し、化合物(A-2)を含む混合物を得た。[A]化合物(A-2)を含む混合物中の溶媒以外の成分の濃度は、14質量%であった。
下記表1に示す種類及び使用量の[m]化合物、[x]化合物、[d]溶媒を使用した以外は、合成例1-1と同様にして、[A]化合物(A-10)、(A-14)を得た。
下記表1に示す種類及び使用量の[m]化合物、[x]化合物、[d]溶媒、[C]溶媒を使用した以外は、合成例1-2と同様にして、[A]化合物(A-3)~(A-9)及び(A-11)~(A-13)を含む混合物を得た。
窒素雰囲気下、反応容器内において化合物(m-4)を投入した。上記反応容器において、室温(25℃~30℃)で攪拌しながら、化合物(x-6)(モル比2)を30分かけて滴下した。次いで、60℃で反応を2時間実施した。反応終了後、反応容器内を30℃以下に冷却した。冷却した反応溶液を、溶媒(d-4)(900質量部)で希釈した。上記反応容器内において、室温(25℃~30℃)で攪拌しながら、水(モル比2)を10分かけて滴下した。次いで、60℃で加水分解縮合反応を2時間実施した。加水分解縮合反応終了後、反応容器内を30℃以下に冷却した。冷却した反応溶液に、溶媒(C-2)1,000質量部を加えた後、エバポレーターを用いて、水、イソプロパノール、反応により生成したアルコール、水及び余剰の溶媒(C-2)を除去して、化合物(A-15)を含む混合物を得た[A]化合物(A-15)を含む混合物中の溶媒以外の成分の濃度は、13質量%であった。化合物(A-15)のMwは2,800であった。
下記表1に示す種類及び使用量の[m]化合物、[x]化合物、[d]溶媒及び[C]溶媒を使用した以外は、合成例1-15と同様にして、[A]化合物(A-16)を含む混合物を得た。化合物(A-16)のMwは1,600であった。
[B]重合体として、下記式(B-1)~(B-10)及び(b-1)で表される重合体(以下、「重合体(B-1)~(B-10)及び(b-1)」ともいう)を以下に示す手順により合成した。
1,1,1,3,3,3-ヘキサフルオロイソプロピルメタクリレート43.0g及びビニルベンジルアルコール57.0gをメチルイソブチルケトン130gに溶解させ、2,2’-アゾビス(2-メチルプロピオン酸)ジメチル19.6gを添加し、単量体溶液を調製した。反応容器に、窒素雰囲気下、メチルイソブチルケトン70gを入れ、80℃に加熱し、攪拌しながら、上記単量体溶液を3時間かけて滴下した。滴下開始を重合反応の開始時間とし、重合反応を6時間実施した後、30℃以下に冷却した。反応溶液に酢酸プロピレングリコールモノメチルエーテル300gを加え、メチルイソブチルケトンを減圧濃縮により除去し、重合体(B-1)の酢酸プロピレングリコールモノメチルエーテル溶液を得た。重合体(B-1)のMwは4,200であった。
上記式(B-2)~(B-10)及び(b-1)に示す各構造単位を各含有割合(モル%)で与える各単量体を用いた以外は合成例2-1と同様にして、重合体(B-2)~(B-10)及び(b-1)の酢酸プロピレングリコールモノメチルエーテル溶液を得た。重合体(B-2)のMwは3,800、重合体(B-3)のMwは4,000、重合体(B-4)のMwは4,300、重合体(B-5)のMwは4,500、重合体(B-6)のMwは4,100、重合体(B-7)のMwは4,100、重合体(B-8)のMwは4,200、重合体(B-9)のMwは4,200、重合体(B-10)のMwは4,300、重合体(b-1)のMwは4,100であった。
組成物の調製に用いた[A]化合物、[B]重合体、[C]溶媒及び[F]その他の任意成分を以下に示す。
C-3:シクロヘキサノン
C-4:2-ヘプタノン
C-5:メシチレン
C-6:酢酸ブチル
F-1:4-メトキシフェノール
F-2:界面活性剤((株)ネオスの「NBX-15」)
F-3:界面活性剤(DIC(株)の「F563」)
下記表2に示すように、[A]化合物(A-1)10質量部に対して、[B]重合体(B-1)が0.05質量部、[C]溶媒としての(C-3)が90質量部となるように混合した。得られた溶液を孔径0.2μmのポリテトラフルオロエチレン(PTFE)フィルターでろ過して、組成物(J-1)を調製した。下記表2中の[B]重合体及び[F]その他の任意成分における「-」は、[B]重合体及び[F]その他の任意成分を使用しなかったことを示す。以下同様である。
下記表2に示すように、[A]化合物(A-2)を含む混合物と[C]溶媒としての(C-1)とを、[A]化合物(A-2)中の溶媒以外の成分10質量部に対して、[B]重合体(B-1)が0.05質量部、[C]溶媒が90質量部([A]化合物を含む混合物に含まれる[C]溶媒も含む)となるように混合した。得られた溶液を孔径0.2μmのポリテトラフルオロエチレン(PTFE)フィルターでろ過して、組成物(J-2)を調製した。
各成分の種類及び含有量を下記表2に示す通りとした以外は、実施例1-1又は実施例1-2と同様に操作して、組成物(J-3)~(J-38)を調製した。
各成分の種類及び含有量を下記表2に示す通りとした以外は、実施例1-2と同様に操作して、組成物(j-1)~(j-4)を調製した。
上記調製した各組成物を用い、塗工性、ウエハエッジ除去性及びハンプ抑制性を下記方法に従って評価した。評価結果を下記表3に示す。
上記調製した直後の組成物をシリコンウェハ(基板)上にスピンコーター(東京エレクトロン(株)の「CLEAN TRACK ACT8」)を用い、回転塗工法により塗工した後、1,500rpmで回転させながら、基板の外周端部から基板の中心への長さが2mmの位置へ、除去液吐出ノズルを1秒あたり1mmの速度で移動させながら、除去液(プロピレングリコールモノメチルエーテルアセテート/プロピレングリコールモノエチルエーテル=30/70、質量比)を1秒あたり2mlの吐出量で吐出し、基板の外周端部から基板の中心への長さが2mmの位置で上記除去液を1秒あたり2mlの吐出量で10秒間吐出した後、除去液の吐出を停止し、この基板を1,500rpm及び30秒間の条件で回転させた。次に、この基板を450℃で60秒間加熱することにより、平均厚み30nmレジスト下層膜付き基板を得た。
塗工性について、上記レジスト下層膜付き基板を目視で観察し、円形状の塗工欠陥が見られない場合は「A」(良好)と、円形状の塗工欠陥が1個以上ある場合は「B」(不良)と評価した。
ウエハエッジ除去性について、上記レジスト下層膜付き基板の外周端部から基板の中心への長さが5mmまでのウエハ周辺部分を光学顕微鏡(倍率10倍)で観察し、除去ムラが見られなかった場合は「A」(良好)と、除去ムラが見られた場合は「B」(不良)と評価した。図1Aは、ウエハエッジ除去性の評価で除去ムラが見られなかった場合の光学顕微鏡写真であり、図1Bは、ウエハエッジ除去性の評価で除去ムラが見られた場合の光学顕微鏡写真である。
ハンプ抑制性について、上記レジスト下層膜付き基板の外周端部から基板の中心への長さが10mmまでの位置の高さ変化を、触針式段差計(KLA Alpha-Step D-600、触針圧5mg)を用いて測定した。レジスト下層膜の無い基板の高さを0とした場合に、高さが40nm未満の場合は「A」(良好)と、高さが40nm以上50nm未満の場合は「B」(やや良好不良)、高さが50nm以上の場合は「C」(不良)と評価した。
Claims (15)
- 金属化合物と、
下記式(1)で表される第1構造単位及び下記式(2)で表される第2構造単位を有する重合体と、
溶媒と
を含有する、レジスト下層膜形成用組成物。
- 上記金属化合物10質量部に対する上記重合体の含有量が0.00001質量部以上2質量部以下である、請求項1に記載のレジスト下層膜形成用組成物。
- R2が置換又は非置換の炭素数1~20の1価の鎖状炭化水素基である、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- R2が置換の炭素数1~20の1価の鎖状炭化水素基であり、上記鎖状炭化水素基が有する水素原子の一部又は全部がフッ素原子で置換されている、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- 式(2)中、nは、1~8の整数であり、少なくとも1つのR4がモノヒドロキシアルキル基である、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- 上記モノヒドロキシアルキル基がモノヒドロキシメチル基である、請求項5に記載のレジスト下層膜形成用組成物。
- 上記重合体を構成する全構造単位に占める上記第1構造単位の含有割合が10モル%以上90モル%以下である、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- 上記重合体を構成する全構造単位に占める上記第2構造単位の含有割合が10モル%以上90モル%以下である、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- 上記金属化合物に含まれる金属原子が、周期表第3族~第16族に属する、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- 上記金属化合物に含まれる金属原子が、周期表第4族に属する、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- レジスト下層膜形成用組成物に含有される全成分に占める上記金属化合物の含有割合が2質量%以上30質量%以下である、請求項1又は請求項2に記載のレジスト下層膜形成用組成物。
- 基板に、直接又は間接に、レジスト下層膜形成用組成物を塗工する工程と、
上記塗工工程により形成されたレジスト下層膜に、直接又は間接に、レジストパターンを形成する工程と、
上記レジストパターンをマスクとしたエッチングにより上記レジスト下層膜にパターンを形成する工程と
を含み、
上記レジスト下層膜形成用組成物が、
金属化合物と、
下記式(1)で表される第1構造単位及び下記式(2)で表される第2構造単位を有する重合体と、
溶媒と
を含有する、半導体基板の製造方法。
- 上記レジストパターン形成工程より前に、
上記塗工工程により形成されたレジスト下層膜に、直接又は間接に、有機下層膜を形成する工程
をさらに含む、請求項12に記載の半導体基板の製造方法。 - 上記レジストパターン形成工程より前に、
上記塗工工程により形成されたレジスト下層膜に、直接又は間接に、ケイ素含有膜を形成する工程
をさらに含む、請求項12又は請求項13に記載の半導体基板の製造方法。 - 基板に直接又は間接にレジスト下層膜形成用組成物を塗工する工程
を備え、
上記レジスト下層膜形成用組成物が、
金属化合物と、
下記式(1)で表される第1構造単位及び下記式(2)で表される第2構造単位を有する重合体と、
溶媒と
を含有する、レジスト下層膜の形成方法。
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KR1020247002773A KR20240037974A (ko) | 2021-07-28 | 2022-07-08 | 레지스트 하층막 형성용 조성물, 반도체 기판의 제조 방법 및 레지스트 하층막의 형성 방법 |
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JP2013185155A (ja) * | 2012-03-06 | 2013-09-19 | Rohm & Haas Electronic Materials Llc | メタルハードマスク組成物 |
JP2016532739A (ja) * | 2013-06-28 | 2016-10-20 | アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | 可溶性金属酸化物カルボキシレートのスピンオン組成物及びそれらの使用方法 |
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JP2013185155A (ja) * | 2012-03-06 | 2013-09-19 | Rohm & Haas Electronic Materials Llc | メタルハードマスク組成物 |
JP2016532739A (ja) * | 2013-06-28 | 2016-10-20 | アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | 可溶性金属酸化物カルボキシレートのスピンオン組成物及びそれらの使用方法 |
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