KR101557816B1 - 레지스트 조성물 및 이를 이용한 패턴 형성 방법 - Google Patents
레지스트 조성물 및 이를 이용한 패턴 형성 방법 Download PDFInfo
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- KR101557816B1 KR101557816B1 KR1020080085858A KR20080085858A KR101557816B1 KR 101557816 B1 KR101557816 B1 KR 101557816B1 KR 1020080085858 A KR1020080085858 A KR 1020080085858A KR 20080085858 A KR20080085858 A KR 20080085858A KR 101557816 B1 KR101557816 B1 KR 101557816B1
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- 238000000034 method Methods 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 239000011347 resin Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000001723 curing Methods 0.000 claims description 18
- 230000008878 coupling Effects 0.000 claims description 17
- 238000010168 coupling process Methods 0.000 claims description 17
- 238000005859 coupling reaction Methods 0.000 claims description 17
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 12
- -1 acryl group Chemical group 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- NAKNWEYGAKQQBY-UHFFFAOYSA-N 2,4-dioxabicyclo[1.1.0]butane-1,3-diol Chemical compound O1C2(O)OC21O NAKNWEYGAKQQBY-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- IQYMRQZTDOLQHC-ZQTLJVIJSA-N [(1R,4S)-2-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@H]2C(OC(=O)C=C)C[C@@H]1C2 IQYMRQZTDOLQHC-ZQTLJVIJSA-N 0.000 claims description 6
- SKKHNUKNMQLBTJ-QIIDTADFSA-N [(1s,4r)-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@H]2C(OC(=O)C(=C)C)C[C@@H]1C2 SKKHNUKNMQLBTJ-QIIDTADFSA-N 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 5
- 125000005641 methacryl group Chemical group 0.000 claims description 5
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 4
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000005530 etching Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000004380 ashing Methods 0.000 claims description 2
- 238000000016 photochemical curing Methods 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
- 239000010408 film Substances 0.000 description 30
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- 125000005587 carbonate group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- GPGCGIBSOKNTEU-UHFFFAOYSA-N CCCCCCOC(C=C)=O.N=C=O Chemical compound CCCCCCOC(C=C)=O.N=C=O GPGCGIBSOKNTEU-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
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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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- 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
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
-
- 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
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/128—Radiation-activated cross-linking agent containing
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- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nanotechnology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
Claims (21)
- 삭제
- 삭제
- 제1항에서,상기 저분자 수지의 분자량은 50 내지 300 인 레지스트 조성물.
- 제1항에서,상기 저분자 수지는 노보닐 아크릴레이트(norbornyl acrylate), 노보닐 메타크릴레이트(norbornyl methacrylate), 노말헥실 아크릴레이트(normalhexyl acrylate), 노말헥실 메타크릴레이트(normalhexyl methacrylate), 이소보닐 아크릴레이트(isobonyl acrylate), 이소보닐 메타크릴레이트(isobonyl methacrylate), 에틸렌글리콜디아크릴레이트(ethyleneglycoldiacrylate), 에틸렌글리콜디메타크릴레이트(ethyleneglycoldimethacrylate), 디에폭시에틸렌글리콜(diepoxyethyleneglycol) 중에서 선택되는 적어도 하나인 레지스트 조성물.
- 제1항에서,상기 제1 및 제2 결합부는 빛에 감응하여 라디칼 또는 산을 생성하거나 별도의 광개시제에 의하여 가교 결합할 수 있는 작용기를 포함하는 레지스트 조성물.
- 제6항에서,상기 제1 및 제2 결합부는 아크릴기(acryl group), 메타크릴기(methacryl group), 신나모일기(cinnamoyl group) 및 에폭시기(epoxy group)를 각각 포함하는 화합물 중에서 선택되는 적어도 하나인 레지스트 조성물.
- 제1항에서,노광시 상기 제1 결합부 및 상기 제2 결합부가 광반응하여 상호 가교 결합되는 레지스트 조성물.
- 제8항에서,상기 노광 후 열처리 시 상기 중심부는 저분자화된 구조로 변성되는 레지스트 조성물.
- 기판 위에 실리콘막, 실리콘 산화막, 실리콘 질화막, 금속막, 금속 산화막 중에서 선택된 어느 하나로 패턴 형성부를 도포하는 단계,도포된 상기 패턴 형성부 위에 열분해 가능한 중심부 및 광반응 가능한 제1 결합부로 이루어진 경화제와 저분자 수지 및 광반응 가능한 제2 결합부로 이루어진 용매를 포함하는 레지스트 조성물을 도포하여 레지스트막을 형성하는 단계,도포된 상기 레지스트막 위에 볼록부, 오목부 및 본체부를 가진 몰드를 배치하는 단계,상기 몰드를 사용하여 상기 레지스트막을 압인(imprinting)하여 패턴부 및 비패턴부를 포함하는 프리 레지스트 패턴을 형성하는 단계,압인된 상기 프리 레지스트 패턴을 노광하여 경화 레지스트 패턴을 형성하는 단계,상기 경화 레지스트 패턴으로부터 상기 몰드를 분리하는 단계,상기 경화 레지스트 패턴을 애싱하여 상기 비패턴부를 제거함으로써 레지스트 패턴을 형성하는 단계, 그리고상기 레지스트 패턴을 에칭 공정에 적용하여 상기 패턴 형성부에 소정의 패턴을 형성하는 단계를 포함하고,상기 중심부는 하기 화학식 1 내지 3 중 어느 하나인 패턴 형성 방법:[화학식 1][화학식 2][화학식 3]상기 식에서, R은 R1, R2, R3, R4, 또는 H이며,
- 제10항에서,상기 레지스트 패턴을 열처리하는 단계, 그리고열처리된 상기 레지스트 패턴을 스트리핑하는 단계를 더 포함하는 패턴 형성 방법.
- 삭제
- 삭제
- 제10항에서,상기 저분자 수지의 분자량은 100 내지 300 인 패턴 형성 방법.
- 제14항에서,상기 저분자 수지는 노보닐 아크릴레이트(norbornyl acrylate), 노보닐 메타크릴레이트(norbornyl methacrylate), 노말헥실 아크릴레이트(normalhexyl acrylate), 노말헥실 메타크릴레이트(normalhexyl methacrylate), 이소보닐 아크릴레이트(isobonyl acrylate), 이소보닐 메타크릴레이트(isobonyl methacrylate), 에틸렌글리콜디아크릴레이트(ethyleneglycoldiacrylate), 에틸렌글리콜디메타크릴레이트(ethyleneglycoldimethacrylate), 디에폭시에틸렌글리콜(diepoxyethyleneglycol) 중에서 선택되는 적어도 하나인 패턴 형성 방법.
- 제10항에서,상기 제1 및 제2 결합부는 빛에 감응하여 라디칼 또는 산을 생성하거나 별도의 광개시제에 의하여 가교 결합할 수 있는 작용기를 포함하는 패턴 형성 방법.
- 제16항에서,상기 제1 및 제2 결합부는 아크릴기(acryl group), 메타크릴기(methacryl group), 신나모일기(cinnamoyl group) 및 에폭시기(epoxy group)를 각각 포함하는 화합물 중에서 선택되는 적어도 하나인 패턴 형성 방법.
- 제10항에서,상기 경화 레지스트 패턴을 형성하는 단계에서, 상기 노광은 365 nm의 파장에서 1 내지 2 분간 실시하는 패턴 형성 방법.
- 제10항에서,상기 레지스트 패턴을 열처리하는 단계에서, 상기 열처리는 200℃ 내지 250℃ 에서 30분 내지 1시간 실시하는 패턴 형성 방법.
- 제10항에서,상기 경화 레지스트 패턴을 형성하는 단계는 제1 결합부 및 상기 제2 결합부가 광반응하여 상호 가교 결합되는 패턴 형성 방법.
- 제10항에서,상기 레지스트 패턴을 열처리 하는 단계는 상기 중심부가 저분자화된 구조로 변성되는 패턴 형성 방법.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020080085858A KR101557816B1 (ko) | 2008-09-01 | 2008-09-01 | 레지스트 조성물 및 이를 이용한 패턴 형성 방법 |
US12/363,459 US8053164B2 (en) | 2008-09-01 | 2009-01-30 | Resist composition and method for forming a pattern using the same |
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KR1020080085858A KR101557816B1 (ko) | 2008-09-01 | 2008-09-01 | 레지스트 조성물 및 이를 이용한 패턴 형성 방법 |
Publications (2)
Publication Number | Publication Date |
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KR20100026737A KR20100026737A (ko) | 2010-03-10 |
KR101557816B1 true KR101557816B1 (ko) | 2015-10-07 |
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KR1020080085858A Active KR101557816B1 (ko) | 2008-09-01 | 2008-09-01 | 레지스트 조성물 및 이를 이용한 패턴 형성 방법 |
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CN103897167B (zh) * | 2014-03-21 | 2016-02-24 | 华侨大学 | 含有环氧基的低分子量二氧化碳-环氧化物共聚物及其制备方法 |
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