JP6485875B2 - 化学増幅レジスト組成物および化学増幅レジスト組成物を用いてデバイスを製造する方法 - Google Patents
化学増幅レジスト組成物および化学増幅レジスト組成物を用いてデバイスを製造する方法 Download PDFInfo
- Publication number
- JP6485875B2 JP6485875B2 JP2015555473A JP2015555473A JP6485875B2 JP 6485875 B2 JP6485875 B2 JP 6485875B2 JP 2015555473 A JP2015555473 A JP 2015555473A JP 2015555473 A JP2015555473 A JP 2015555473A JP 6485875 B2 JP6485875 B2 JP 6485875B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- resist composition
- chemically amplified
- amplified resist
- reagent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 238000010894 electron beam technology Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- -1 hydroxymethylene Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 230000005281 excited state Effects 0.000 claims description 4
- 230000005283 ground state Effects 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000005530 etching Methods 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000003321 amplification Effects 0.000 claims 2
- 238000003199 nucleic acid amplification method Methods 0.000 claims 2
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000001603 reducing effect Effects 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- ICVZEJMCWPOEDI-UHFFFAOYSA-N 1-[4-(oxan-2-yl)phenyl]ethanol Chemical compound O1C(CCCC1)C1=CC=C(C=C1)C(C)O ICVZEJMCWPOEDI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000012048 reactive intermediate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OIUWXBBWYFYGRX-UHFFFAOYSA-N 2-[(2-methyl-2-adamantyl)methyl]prop-2-enoic acid Chemical compound C1C(C2)CC3CC1C(C)(CC(=C)C(O)=O)C2C3 OIUWXBBWYFYGRX-UHFFFAOYSA-N 0.000 description 1
- CZJVBHWJFDFPSW-UHFFFAOYSA-N 2-[(3-hydroxy-1-adamantyl)methyl]prop-2-enoic acid Chemical compound C1C(C2)CC3CC2(O)CC1(CC(=C)C(=O)O)C3 CZJVBHWJFDFPSW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000000609 electron-beam lithography Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/24—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part polycyclic without condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/38—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the fluorene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/40—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the anthracene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- 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
- G03F7/16—Coating processes; Apparatus therefor
-
- 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
-
- 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
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
-
- 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
- G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
-
- 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
- G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
- G03F7/2039—X-ray radiation
-
- 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
- G03F7/36—Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma
-
- 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
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Description
4−ヒドロピラニルアセトフェノンの合成
Claims (15)
- 試剤と、酸発生剤と、酸によって開裂可能な結合を有する樹脂と、を含む、化学増幅レジスト組成物であって、
前記試剤に、またはエネルギーを受けるアクセプタにエネルギーを供給すると、前記試剤から中間体が発生され、
前記中間体は前記酸発生剤からの酸の発生を向上させ、
前記中間体はケチルラジカルであり、
前記試剤が、下記式(I)によって表される第1試剤;下記式(II)によって表される第2試剤;並びに、水酸基と、該水酸基および水素原子に結合した炭素原子を含む第1環状部分と、を含む第3試剤;からなる群より選択されるいずれかである、化学増幅レジスト組成物。
R 2 は、フェニル基、アルキルカルボニル基、アリールカルボニル基、アルキル基、アルケニル基、アラルキル基、アルキニル基、環状または多環状部分を含むアルキル基、または炭素原子および水素原子以外の少なくとも1つの原子を含む置換基であり、
R 3 は、水素原子、フェニル基、アルキルカルボニル基、アリールカルボニル基、アルキル基、アルケニル基、アラルキル基、アルキニル基、環状または多環状部分を含むアルキル基、または炭素原子および水素原子以外の少なくとも1つの原子を含む置換基である。)
R 4 は、アリール基、または、芳香族基と該芳香族基上に炭素原子および水素原子以外の少なくとも1つの原子を含む置換基とを含むアリール基であり、
R 5 は、水素原子、フェニル基、アルキルカルボニル基、アリールカルボニル基、アルキル基、アルケニル基、アラルキル基、アルキニル基、環状または多環状部分を含むアルキル基、または炭素原子および水素原子以外の少なくとも1つの原子を含む置換基である。) - 前記第3試剤はさらに第2環状部分を含み、
前記第1環状部分は、前記第2環状部分にも含まれる少なくとも2つの原子を含む、請求項1に記載の化学増幅レジスト組成物。 - 前記第3試剤はさらに第3環状部分を含み、
前記第1環状部分は、前記第3環状部分にも含まれる少なくとも2つの原子を含む、請求項2に記載の化学増幅レジスト組成物。 - 前記第1環状部分は6員環または5員環のいずれかである、請求項1〜3のいずれか一項に記載の化学増幅レジスト組成物。
- 前記第2環状部分は芳香族基である、請求項2に記載の化学増幅レジスト組成物。
- 前記エネルギーの供給を光の照射によって実行する、請求項1〜5のいずれか一項に記載の化学増幅レジスト組成物。
- 前記エネルギーの供給を、波長が15nm以下である光および電子線の少なくとも1つで前記試剤を照射することによって実行する、請求項1〜6のいずれか一項に記載の化学増幅レジスト組成物。
- 前記中間体は、前記試剤から水素原子を引き抜くことによって発生する、請求項1〜7のいずれか一項に記載の化学増幅レジスト組成物。
- 前記中間体の基底状態の第1酸化電位および励起状態の第2酸化電位の少なくとも1つと、前記酸発生剤の基底状態の第1還元電位および励起状態の第2還元電位の少なくとも1つとの差は、0.10eV以上である、請求項1〜8のいずれか一項に記載の化学増幅レジスト組成物。
- 前記第1還元電位は前記第1酸化電位および前記第2酸化電位の少なくとも1つより低い、請求項9に記載の化学増幅レジスト組成物。
- 前記酸発生剤はヨードニウムイオンまたはスルホニウムイオンを含む有機塩である、請求項1〜10のいずれか一項に記載の化学増幅レジスト組成物。
- デバイスを製造する方法であって、
請求項1〜11のいずれか一項に記載の化学増幅レジスト組成物の溶液を基板に塗布して、前記化学増幅レジスト組成物を含む膜が前記基板上に形成されるようにすること、および、
前記膜の第2部分が電磁線および粒子線の少なくとも1つで照射されない一方で、前記膜の第1部分が電磁線および粒子線の少なくとも1つで照射されるように、電磁線および粒子線の少なくとも1つで前記膜を照射すること、を含む、方法。 - 前記第1部分を取り除くことをさらに含む、請求項12に記載の方法。
- 前記第1部分が存在した前記基板の第3部分がエッチングされるように前記基板をエッチングすることを含む、請求項12または13に記載の方法。
- 前記膜の照射を、EUV光および電子線の少なくとも1つを使用して実行する、請求項12〜14のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361822603P | 2013-05-13 | 2013-05-13 | |
US61/822,603 | 2013-05-13 | ||
PCT/JP2014/002531 WO2014185065A1 (en) | 2013-05-13 | 2014-05-13 | Reagent and composition of resist |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016526052A JP2016526052A (ja) | 2016-09-01 |
JP6485875B2 true JP6485875B2 (ja) | 2019-03-20 |
Family
ID=51898054
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015555473A Active JP6485875B2 (ja) | 2013-05-13 | 2014-05-13 | 化学増幅レジスト組成物および化学増幅レジスト組成物を用いてデバイスを製造する方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US9618844B2 (ja) |
JP (1) | JP6485875B2 (ja) |
KR (1) | KR20160006721A (ja) |
CN (1) | CN105308146A (ja) |
TW (1) | TWI632231B (ja) |
WO (1) | WO2014185065A1 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7771293B1 (en) | 2005-11-22 | 2010-08-10 | Kayode Teddy Vann | Basketball shooting training aid and method for its use |
TWI632231B (zh) | 2013-05-13 | 2018-08-11 | 東洋合成工業股份有限公司 | 化學放大阻劑組成物和製造裝置之方法 |
CN105339457B (zh) | 2013-06-24 | 2018-07-20 | 东洋合成工业株式会社 | 用于增强化学物质产生的试剂 |
US10031416B2 (en) | 2013-08-07 | 2018-07-24 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
WO2015052914A1 (en) * | 2013-10-07 | 2015-04-16 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species and manufacturing apparatus |
US9567277B2 (en) | 2013-10-08 | 2017-02-14 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
JP2015134904A (ja) | 2013-11-18 | 2015-07-27 | 東洋合成工業株式会社 | 化学種発生向上化合物 |
JP6774814B2 (ja) | 2015-08-20 | 2020-10-28 | 国立大学法人大阪大学 | 化学増幅型レジスト材料及びパターン形成方法 |
JP6809843B2 (ja) | 2015-08-20 | 2021-01-06 | 国立大学法人大阪大学 | パターン形成方法 |
JP6512994B2 (ja) | 2015-08-20 | 2019-05-15 | 国立大学法人大阪大学 | 化学増幅型レジスト材料 |
JP6507958B2 (ja) | 2015-09-10 | 2019-05-08 | Jsr株式会社 | 化学増幅型レジスト材料及びレジストパターン形成方法 |
JP2017054116A (ja) | 2015-09-10 | 2017-03-16 | Jsr株式会社 | レジストパターン形成方法 |
US10018911B2 (en) | 2015-11-09 | 2018-07-10 | Jsr Corporation | Chemically amplified resist material and resist pattern-forming method |
US9989849B2 (en) | 2015-11-09 | 2018-06-05 | Jsr Corporation | Chemically amplified resist material and resist pattern-forming method |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3042701B2 (ja) | 1990-10-30 | 2000-05-22 | 株式会社日立製作所 | パターン形成法 |
JPH07239547A (ja) * | 1993-04-16 | 1995-09-12 | Hitachi Ltd | レジスト及びそのパターン形成方法 |
EP0919867B1 (de) | 1997-11-28 | 2003-05-21 | Infineon Technologies AG | Chemisch verstärkter Resist für die Elektronenstrahllithographie |
JP4838437B2 (ja) * | 2000-06-16 | 2011-12-14 | Jsr株式会社 | 感放射線性樹脂組成物 |
US7514764B2 (en) | 2005-03-23 | 2009-04-07 | Wisconsin Alumni Research Foundation | Materials and methods for creating imaging layers |
JP2013031125A (ja) | 2011-07-29 | 2013-02-07 | Toshiba Corp | 音信号処理装置、および音信号処理方法 |
JP5261756B1 (ja) | 2012-03-30 | 2013-08-14 | 株式会社フジクラ | 多層配線基板 |
JP5988115B2 (ja) | 2013-02-20 | 2016-09-07 | 国立大学法人大阪大学 | レジストパターン形成方法 |
TWI632231B (zh) | 2013-05-13 | 2018-08-11 | 東洋合成工業股份有限公司 | 化學放大阻劑組成物和製造裝置之方法 |
-
2014
- 2014-05-13 TW TW103116796A patent/TWI632231B/zh active
- 2014-05-13 CN CN201480027633.XA patent/CN105308146A/zh active Pending
- 2014-05-13 JP JP2015555473A patent/JP6485875B2/ja active Active
- 2014-05-13 KR KR1020157034479A patent/KR20160006721A/ko not_active Application Discontinuation
- 2014-05-13 US US14/891,293 patent/US9618844B2/en active Active
- 2014-05-13 WO PCT/JP2014/002531 patent/WO2014185065A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
JP2016526052A (ja) | 2016-09-01 |
US9618844B2 (en) | 2017-04-11 |
WO2014185065A1 (en) | 2014-11-20 |
KR20160006721A (ko) | 2016-01-19 |
TWI632231B (zh) | 2018-08-11 |
TW201500528A (zh) | 2015-01-01 |
CN105308146A (zh) | 2016-02-03 |
US20160070165A1 (en) | 2016-03-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6485875B2 (ja) | 化学増幅レジスト組成物および化学増幅レジスト組成物を用いてデバイスを製造する方法 | |
JP6525269B2 (ja) | 化学増幅型レジスト組成物および装置の製造方法 | |
JP6537118B2 (ja) | 化学増幅フォトレジスト組成物及び装置の製造方法 | |
JP2016531953A (ja) | 化学種発生向上試剤 | |
US9567277B2 (en) | Reagent for enhancing generation of chemical species | |
JP5111106B2 (ja) | カリックスレゾルシナレン化合物、並びに、それからなるフォトレジスト基材及びその組成物 | |
US9790241B2 (en) | Reagent for enhancing generation of chemical species | |
JP2016530339A (ja) | 化学種発生向上試剤 | |
JP4854023B2 (ja) | 感光性組成物 | |
JP2015098471A (ja) | 化学種発生向上試剤 | |
JP2015134904A (ja) | 化学種発生向上化合物 | |
JPWO2005097725A1 (ja) | カリックスレゾルシナレン化合物、フォトレジスト基材及びその組成物 | |
JP2016539201A (ja) | 化学種発生向上試剤 | |
JP2004191913A (ja) | フォトレジスト基材及びその組成物 | |
TW201602718A (zh) | 用以提升化學物種之產生的試劑及製造裝置 | |
JP4921160B2 (ja) | 感光性樹脂及び感光性組成物 | |
JP2016204283A (ja) | 新規な化合物、光塩基発生剤、および新規な化合物の製造方法 | |
JP2005075767A (ja) | フォトレジスト基材及びその精製方法、並びにフォトレジスト組成物 | |
WO2012133040A1 (ja) | カリックスアレーン誘導体 | |
JP2015061823A (ja) | 化合物及び該化合物からなる光塩基発生剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20161205 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20161205 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170510 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20170710 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20170710 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180612 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180809 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190115 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190214 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6485875 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |