JP6577904B2 - 光塩基発生剤及びそれを含むフォトレジスト組成物 - Google Patents
光塩基発生剤及びそれを含むフォトレジスト組成物 Download PDFInfo
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- JP6577904B2 JP6577904B2 JP2016088986A JP2016088986A JP6577904B2 JP 6577904 B2 JP6577904 B2 JP 6577904B2 JP 2016088986 A JP2016088986 A JP 2016088986A JP 2016088986 A JP2016088986 A JP 2016088986A JP 6577904 B2 JP6577904 B2 JP 6577904B2
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- OIHCCWXZFYNOJS-UHFFFAOYSA-N [2,3-bis-(4-methylphenyl)sulfonyloxyphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C=2C=CC(C)=CC=2)=C1OS(=O)(=O)C1=CC=C(C)C=C1 OIHCCWXZFYNOJS-UHFFFAOYSA-N 0.000 description 1
- HKKMPPDCCCBZHM-UHFFFAOYSA-M [4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 HKKMPPDCCCBZHM-UHFFFAOYSA-M 0.000 description 1
- QFKJMDYQKVPGNM-UHFFFAOYSA-N [benzenesulfonyl(diazo)methyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=CC=C1 QFKJMDYQKVPGNM-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- XCCCHWWMLSAIOH-UHFFFAOYSA-N anthracen-1-ylmethanol Chemical class C1=CC=C2C=C3C(CO)=CC=CC3=CC2=C1 XCCCHWWMLSAIOH-UHFFFAOYSA-N 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000000994 contrast dye Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- BQUDLWUEXZTHGM-UHFFFAOYSA-N ethyl propaneperoxoate Chemical compound CCOOC(=O)CC BQUDLWUEXZTHGM-UHFFFAOYSA-N 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/14—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/68—Preparation processes not covered by groups G03F1/20 - G03F1/50
- G03F1/76—Patterning of masks by imaging
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/325—Non-aqueous compositions
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
Landscapes
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- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
X1−R1−O−C(=O)N(R2)R3 (I)
式中、
X1は、任意選択で置換された芳香族基であり、
R1は、リンカーであり、
R2及びR3は、同じもしくは異なる任意選択で置換された直鎖、分岐、もしくは環状脂肪族基、または任意選択で置換された芳香族基であり、
R2及びR3のうちの少なくとも1つは、4個以上の炭素原子を有する任意選択で置換された分岐アルキル基である。
好ましい光塩基発生剤は、比較的減少した表面張力を有することができる。いかなる理論にも束縛されるものではないが、かかる有利な表面活性は、ネガティブトーン現像プロセス中のより良好なフォトレジストトッププロファイルを含む顕著な性能利点を提供することができる。
X1−R1−O−C(=O)N(R2)R3 (I)
式中、
X1は、任意選択で置換された芳香族基であり、
R1は、リンカーであり、
R2及びR3は、同じもしくは異なる任意選択で置換された直鎖、分岐、もしくは環状脂肪族基、または任意選択で置換された芳香族基であり、
R2及びR3のうちの少なくとも1つは、4個以上の炭素原子を有する任意選択で置換された分岐アルキル基である。
X1−(CYZ)n−O−C(=O)N(R2)R3 (IA)
X1−(CY’=CZ’)n−(CY’Z’)n’−O−C(=O)N(R2)R3 (IB)
式中、式(IA)及び(IB)の各々では、
X1は、任意選択で置換された芳香族基であり、
各Y、Z、Y’、及びZ’は、独立して、水素または非水素置換基、例えば、フルオロを含むハロゲン、任意選択で置換されたアルキル、任意選択で置換されたアルコキシなどであり、
n及びn’は各々、好適には1〜12、好ましくは1または2、特に1の正の整数であり、
R2及びR3は、同じもしくは異なる任意選択で置換された直鎖、分岐、もしくは環状脂肪族基、または任意選択で置換された芳香族基であり、
R2及びR3のうちの少なくとも1つは、4個以上の炭素原子を有する任意選択で置換された分岐アルキル基である。
本発明のフォトレジストは、典型的には、ポリマー、1つ以上の酸発生剤、及び本明細書に開示される1つ以上の光塩基発生剤化合物を含む。好ましくは、レジストポリマーは、アルカリ性水溶解性をレジスト組成物に与える官能基を有する。例えば、ヒドロキシルもしくはカルボキシレートなどの極性官能基、またはリソグラフィ処理時にかかる極性部分を遊離させることができる酸に不安定な基を含むポリマーが好ましい。好ましくは、ポリマーは、アルカリ性水溶液で現像可能なレジストを与えるのに十分な量で、レジスト組成物中で使用される。
193nmなどのサブ200nmで撮像されるフォトレジストにおける使用に好ましい樹脂は、以下の一般式(I)、(II)、及び(III)の単位を含み、
上のスキーム1に概ね描写されるように、1,1’−カルボニルジイミダゾール(5.3g、1.0当量)を、窒素雰囲気下で無水DMF(60mL)中に懸濁させた。溶液を0℃に冷却し、無水DMF(40mL)中の(2−ニトロフェニル)メタノール(5.0g、1.0当量)を緩徐に添加した。室温で3時間撹拌した後、ジオクチルアミン(7.88g、1.0当量)を添加した。混合物を70℃で20時間撹拌した。反応混合物をEAで希釈し、水で洗浄した。有機相を硫酸ナトリウム上で乾燥させ、濾過し、減圧下で濃縮した。標記化合物の粗化合物をフラッシュクロマトグラフィー(EtOAc/ヘプタン)によって精製した。
上のスキーム2に概ね描写されるように、トリホスゲン(1.16g、0.3当量)を、窒素雰囲気下で無水DCM(30mL)中に懸濁させた。溶液を0℃に冷却した。次いで、無水DCM(30mL)中の(2−ニトロフェニル)メタノール(2.0g、1.0当量)及びN,N−ジイソプロピルエチレンアミン(3.38g、2.0当量)を添加した。室温で3時間撹拌した後、ビス(2−エチルヘキシル)アミン(3.15g、1.0当量)を緩徐に添加し、4時間撹拌した。反応混合物を水で洗浄し、有機相を硫酸ナトリウム上で乾燥させ、濾過し、減圧下で濃縮した。粗標記化合物を、フラッシュクロマトグラフィー(EtOAc/ヘプタン)によって精製した。
上のスキーム3に概ね描写されるように、トリホスゲン(2.137g、0.5当量)を、窒素雰囲気下で無水DCM(30mL)中に懸濁させた。溶液を0℃に冷却した。次いで、無水DCM(100mL)中の、9−(ヒドロキシメチル)アントラセン(3.0g、1.0当量)及びN,N−ジイソプロピルエチレンアミン(3.723g、2.0当量)を添加した。室温で3時間撹拌した後、ビス(2−エチルヘキシル)アミン(3.478g、1.0当量)を緩徐に添加し、4時間撹拌した。反応混合物を水で洗浄し、有機相を硫酸ナトリウム上で乾燥させ、濾過し、減圧下で濃縮した。粗標記化合物を、フラッシュクロマトグラフィー(EtOAc/ヘプタン)によって精製した。
本発明のフォトレジスト組成物を、以下の成分、PGMEA中の13.34gのポリマー−A溶液(20%)、メチル−2−ヒドロキシイソ酪酸中の15.22gのPAG−A溶液(1%)、メチル−2−ヒドロキシイソ酪酸中の5.34gのPAG−B溶液(2%)、メチル−2−ヒドロキシイソ酪酸中の3.53gのWPAG溶液(2%)、PGMEA中の3.57gの消光剤−A溶液(1%)、メチル−2−ヒドロキシイソ酪酸中の0.43gのPBG A溶液(1%)、PGMEA中の1.24gのEBL(5%)、33.07gのPGMEA、9.69gのγ−ブチロラクトン、及び14.57gのメチル−2−ヒドロキシイソ酪酸を混合することによって調製し、次いで、この混合物を0.2ミクロンのナイロンフィルターで濾過した。このフォトレジスト組成物のポリマー−A、PAG−A、PAG−B、WAG、消光剤−A、EBL、及びPBG Aは以下の構造を有する。
本発明のフォトレジスト組成物は、以下の成分、PGMEA中の13.27gのポリマー−A溶液(20%)、メチル−2−ヒドロキシイソ酪酸中の15.98gのPAG−A溶液(1%)、メチル−2−ヒドロキシイソ酪酸中の5.60gのPAG−B溶液(2%)、メチル−2−ヒドロキシイソ酪酸中の3.53gのWPAG溶液(2%)、PGMEA中の3.92gの消光剤−A溶液(1%)、メチル−2−ヒドロキシイソ酪酸中の0.31gのPBG B溶液(1%)、PGMEA中の1.24gのEBL(5%)、32.78gのPGMEA、9.69gのγ−ブチロラクトン、及び13.67gのメチル−2−ヒドロキシイソ酪酸を混合することによって調製し、次いで、この混合物を0.2ミクロンのナイロンフィルターで濾過した。このフォトレジスト組成物のポリマー−A、PAG−A、PAG−B、WAG、消光剤−A、EBL、及びPBG Bは以下の構造を有する。
HMDSで下塗りされたシリコンウエハ300mmを、AR(商標)26N(Rohm and Haas Electronic Materials)でスピン被覆し、TEL CLEAN TRAC LITHIUS i+上に第1の底部反射防止膜(BARC)を形成し、その後に205℃で60秒間のベークプロセスが続く。
HMDSで下塗りされたシリコンウエハ300mmを、AR(商標)26N(Rohm and Haas Electronic Materials)でスピン被覆し、TEL CLEAN TRAC LITHIUS i+上に第1の底部反射防止膜(BARC)を形成し、その後に205℃で60秒間のベークプロセスが続く。
Claims (9)
- 以下の式(I)に対応する光塩基発生剤であって、
X1−R1−O−C(=O)N(R2)R3 (I)
式中、
X1が、任意選択で置換されたナフチルまたはアントラセニル基であり、
R1が、リンカーであり、
R2及びR3が、同じもしくは異なる任意選択で置換された直鎖、分岐、もしくは環状脂肪族基、または任意選択で置換された芳香族基であり、
R2及びR3のうちの少なくとも1つが、4個以上の炭素原子を有する分岐アルキル基であり、前記4個以上の炭素原子を有する分岐アルキル基が、場合によって置換されていてもよい、前記光塩基発生剤。 - X1が、任意選択で置換されたアントラセニルである、請求項1に記載の光塩基発生剤。
- R2及びR3が各々独立して、4個以上の炭素原子を有する分岐アルキルであり、前記4個以上の炭素原子を有する分岐アルキル基が、場合によって置換されていてもよい、請求項1または2に記載の光塩基発生剤。
- 以下の式(I)に対応する光塩基発生剤であって、
X1−R1−O−C(=O)N(R2)R3 (I)
式中、
X1が、任意選択で置換された芳香族基であり、
R1が、リンカーであり、
R2及びR3が、同じもしくは異なる任意選択で置換された直鎖、分岐、もしくは環状脂肪族基、または任意選択で置換された芳香族基であり、
R2及びR3のうちの少なくとも1つが、4個以上の炭素原子を有する分岐アルキル基であり、前記4個以上の炭素原子を有する分岐アルキル基が、場合によって置換されていてもよく、
R2及び/またはR3が、4個以上の炭素原子を有するフッ素化分岐アルキルである、前記光塩基発生剤。 - (a)樹脂と、
(b)1つ以上の酸発生剤と、
(c)請求項1〜5のいずれか一項に記載の光塩基発生剤と、を含む、フォトレジスト組成物。 - (a)リソグラフィ処理時に極性部分を遊離させることができる酸不安定基を含む樹脂と、
(b)1つ以上の酸発生剤と、
(c)以下の式(IA)に対応する光塩基発生剤であって、
X1−(CYZ)n−O−C(=O)N(R2)R3 (IA)
式中、
X1は、任意選択で置換された芳香族基であり、
各Y及びZは、独立して、水素または非水素置換基であり、
nは正の整数であり、
R2及びR3は、同じもしくは異なる任意選択で置換された直鎖、分岐、もしくは環状脂肪族基、または任意選択で置換された芳香族基であり、ただし、R2及びR3の置換された脂肪族基または芳香族基上の置換基は、(C 1 −C 30 )アルキル、(C 1 −C 30 )アルコキシ、スルホニル、スルホン酸、スルホネートエステル、シアノ、ハロ、ケト、炭素環式アリール、ヘテロ芳香族、炭素脂環式、及びヘテロ脂環式からなる群から選択され、
R2及びR3のうちの少なくとも1つは、4個以上の炭素原子を有する分岐アルキル基であり、前記4個以上の炭素原子を有する分岐アルキル基が、場合によって置換されていてもよい、光塩基発生剤と、を含む、フォトレジスト組成物。 - リソグラフィ処理中に生成される前記光塩基発生剤のアミン開裂生成物が、前記フォトレジスト組成物の被覆層の上方部分へ移動することができる、請求項6または7に記載のフォトレジスト組成物。
- フォトリソグラフィックパターンを形成するための方法であって、
(a)請求項6〜8のいずれか一項に記載のフォトレジスト組成物の層を基板上に適用することと、
(b)前記フォトレジスト組成物層を活性化放射線にパターン露光することと、
(c)前記露光されたフォトレジスト組成物層を現像して、フォトレジストレリーフ像を提供することと、を含む、前記方法。
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