KR100713231B1 - Hard mask composition for resist underlayer film and manufacturing method of semiconductor integrated circuit device using same - Google Patents
Hard mask composition for resist underlayer film and manufacturing method of semiconductor integrated circuit device using same Download PDFInfo
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- KR100713231B1 KR100713231B1 KR1020050130010A KR20050130010A KR100713231B1 KR 100713231 B1 KR100713231 B1 KR 100713231B1 KR 1020050130010 A KR1020050130010 A KR 1020050130010A KR 20050130010 A KR20050130010 A KR 20050130010A KR 100713231 B1 KR100713231 B1 KR 100713231B1
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- formula
- resist underlayer
- hard mask
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- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 239000004065 semiconductor Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229920000642 polymer Polymers 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
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- 239000002253 acid Substances 0.000 claims abstract description 10
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical group O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 14
- 238000005530 etching Methods 0.000 claims description 10
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 claims description 3
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- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 claims 1
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 8
- 238000001312 dry etching Methods 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
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- 238000001459 lithography Methods 0.000 description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
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- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 3
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- NJQJGRGGIUNVAB-UHFFFAOYSA-N 2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one Chemical compound BrC1=CC(Br)(Br)C=C(Br)C1=O NJQJGRGGIUNVAB-UHFFFAOYSA-N 0.000 description 2
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- DAJPMKAQEUGECW-UHFFFAOYSA-N 1,4-bis(methoxymethyl)benzene Chemical compound COCC1=CC=C(COC)C=C1 DAJPMKAQEUGECW-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000015847 Hesperis matronalis Nutrition 0.000 description 1
- 240000004533 Hesperis matronalis Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- MWEGTKYQGBZQCH-UHFFFAOYSA-N OCC=C(C(=O)O)C.C(C(=C)C)(=O)OCO Chemical compound OCC=C(C(=O)O)C.C(C(=C)C)(=O)OCO MWEGTKYQGBZQCH-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- -1 and then Chemical compound 0.000 description 1
- KPRWQUAQLPEFCZ-UHFFFAOYSA-N anthracene;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.C1=CC=CC2=CC3=CC=CC=C3C=C21 KPRWQUAQLPEFCZ-UHFFFAOYSA-N 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000009957 hemming Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
Abstract
본 발명은 레지스트 하층막용 하드마스크 조성물에 관한 것으로서, 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물로부터 생성되는 중합체 또는 화학식 4의 반복단위 및 화학식 5와 화학식 6의 반복단위 중 적어도 하나를 포함하는 중합체와 화학식 3의 고분자, 산 혹은 염기성 촉매, 그리고 유기용매를 포함하는 조성물을 특징으로 하는 레지스트 하층막용 조성물을 제공할 수 있다.The present invention relates to a hard mask composition for a resist underlayer film, the polymer comprising a compound represented by Formula 1 and a compound represented by Formula 2 or a repeating unit of Formula 4 and at least one of the repeating units of Formulas 5 and 6 It is possible to provide a composition for resist underlayer film comprising a composition comprising a polymer, a polymer of formula (3), an acid or basic catalyst, and an organic solvent.
리쏘그래픽, 하드마스크, 반사방지막 Lithographic, Hard Mask, Anti-Reflective Film
Description
본 발명은 레지스트 하층막용 하드마스크 조성물 및 이를 이용한 반도체 집적회로 디바이스의 제조방법에 관한 것으로, 구체적으로 패턴의 재현성이 우수하고, 레지스트와의 밀착성이 우수하며, 레지스트를 노광한 후 사용하는 현상막에 내성이 우수하고 레지스트의 산소 애싱(Ashing)시의 막감소가 적은 레지스트의 하층막용 조성물을 제공할 수 있다.The present invention relates to a hard mask composition for a resist underlayer film and a method for manufacturing a semiconductor integrated circuit device using the same. Specifically, the present invention relates to a developer film which is excellent in reproducibility of a pattern, good adhesion with a resist, and used after exposing the resist. The composition for underlayer film of the resist which is excellent in a resistance and is small in the film reduction at the time of oxygen ashing of a resist can be provided.
대부분의 리쏘그래피 공정은 이미지화층, 예컨대 레지스트 재료층과 기판간의 반사성을 최소화 시키는데 반사방지코팅재료(ARC)을 사용하여 해상도를 증가시킨다. 그러나 이러한 ARC 재료들은 층들의 유사한 기본조성으로 인하여 이미지화층에 불량한 에칭 선택성을 부과한다. 그러므로, 패터닝 후 ARC의 에칭중에 많은 이미지화층도 소모되어, 후속 에칭 단계 중에 추가의 패터닝이 필요하게 되었다.Most lithographic processes increase the resolution by using an antireflective coating material (ARC) to minimize the reflectivity between the imaging layer, such as a layer of resist material and the substrate. However, these ARC materials impose poor etch selectivity on the imaging layer due to the similar basic composition of the layers. Therefore, many imaging layers are also consumed during the etching of ARC after patterning, requiring further patterning during subsequent etching steps.
또한, 일부 리쏘그래피 기술의 경우, 사용된 레지스트 재료는 레지스트 재료 아래에 놓인 층에 소정의 패턴을 효과적으로 전사할 수 있기에 충분한 후속 에 칭 단계에 대한 내성을 제공하지 않는다. 많은 경우에서, 예를 들면 극히 얇은 레지스트 물질이 사용되는 경우, 에칭하고자 하는 기판이 두꺼운 경우, 실질적인 에칭 깊이가 요구되는 경우, 소정의 기판층에 대해 특정한 에칭제를 사용하는 것이 요망되는 경우, 또는 상기 경우의 임의의 조합에서 레지스트 하층막용 하드마스크가 사용된다. 레지스트 하층막용 하드마스크는 패터닝된 레지스트와 패터닝하고자 하는 기판 간의 중간층 역할을 한다. 레지스트 하층막용 하드마스크는 패터닝된 레지스트층으로부터 패턴을 수용하고, 패턴을 기판으로 전사한다. 레지스트 하층막용 하드마스크층은 패턴을 전사하는 데 요구되는 에칭 공정을 견딜수 있어야한다.In addition, for some lithography techniques, the resist material used does not provide sufficient resistance to subsequent etching steps to effectively transfer the desired pattern to the layer underlying the resist material. In many cases, for example when extremely thin resist materials are used, when the substrate to be etched is thick, when substantial etch depth is required, it is desired to use a specific etchant for a given substrate layer, or In any combination of the above cases, a hard mask for resist underlayer film is used. The hard mask for the resist underlayer film serves as an intermediate layer between the patterned resist and the substrate to be patterned. The hard mask for resist underlayer film receives a pattern from the patterned resist layer and transfers the pattern to the substrate. The hard mask layer for the resist underlayer film must be able to withstand the etching process required to transfer the pattern.
일예로, 실리콘 산화막 등의 기판을 가공할 때, 레지스트 패턴을 마스크로 사용하지만 미세화와 함께 레지스트의 두께도 박막화하였기 때문에 레지스트의 마스크성이 부족하여 손상을 주지 않고 산화막을 가공하는 것이 곤란하였다. 따라서 레지스트 패턴을 우선 산화막 가공용 하층막에 전사한 후, 이 막을 마스크로서 산화막에 드라이 에칭 가공하는 공정이 취해진다. 산화막 가공용 하층막이란 하층 반사막을 겸하면서 반사방지막의 하층에 형성되는 막을 뜻한다. 이 공정에서는 레지스트와 산화막 가공용 하층막의 에칭속도가 비슷하기 때문에 레지스트와 상기 하층막사이에 이 하층막을 가공할 수 있는 마스크를 형성할 필요가 있다. 즉, 산화막 상에 산화막 가공용 하층막-하층막 가공용 마스크 -레지스트로 이루어진 다층막이 구성되게 된다.For example, when processing a substrate such as a silicon oxide film, a resist pattern is used as a mask, but since the thickness of the resist is reduced along with miniaturization, it is difficult to process the oxide film without damaging the mask property of the resist. Therefore, the process of first transferring a resist pattern to the underlayer film for oxide film processing, and performing a dry etching process to an oxide film as a mask is taken. The underlayer film for oxide film processing means a film formed under the antireflection film while also serving as a lower reflection film. In this step, since the etching rate of the resist and the underlayer film for oxide film processing is similar, it is necessary to form a mask capable of processing the underlayer film between the resist and the underlayer film. That is, a multilayer film made of an oxide film processing underlayer film-underlayer film processing mask-resist is formed on the oxide film.
하층막 가공용 마스크 아래 형성되는 산화막 가공용 마스크의 굴절율, 흡광도 및 두께에 따라 적합한 하층막 가공용 마스크의 굴절률과 흡광도가 변하게 된 다.The refractive index and the absorbance of a suitable mask for lower layer film processing change according to the refractive index, absorbance, and thickness of the mask for oxide film processing formed under the mask for lower layer film processing.
하층막 가공용 마스크에 요구되는 특성으로 헤밍(hemming)현상 등이 없는 레지스트 패턴을 형성할 수 있는 것, 레지스트와의 밀착성이 우수한 것, 산화막 가공용 하층막을 가공할 때 충분한 마스크성이 있는 것을 들 수 있지만, 모든 요구를 충족시키는 재료를 찾는 것은 어렵다. 특히 하층막 가공용 마스크의 굴절율과 흡광도가 적절치 않아 반사방지특성을 효과적으로 사용하지 못하고 이에 리쏘그래피 공정마진을 확보하지 못하는 문제점이 있었다.The characteristics required for the mask for underlayer film processing include those capable of forming a resist pattern without hemming, etc., excellent adhesion to the resist, and those having sufficient mask property when processing the underlayer film for oxide film processing. It is difficult to find a material that meets all needs. In particular, the refractive index and the absorbance of the mask for the underlayer film processing is not appropriate, there is a problem that can not effectively use the anti-reflection characteristics and thus the lithography process margin is not secured.
본 발명에서는 상기한 종래기술의 문제점을 극복하여 하층막용 하드마스크의 굴절율, 흡광도를 최적화 함에 따라 반사방지특성을 효과적으로 사용하여 이에 리쏘그래피 공정마진을 확보할수 있는 신규한 레지스트 하층막용 하드마스크 조성물을 제공하는 것을 목적으로 한다.The present invention provides a novel resist underlayer hard mask composition for overcoming the above-mentioned problems of the prior art and effectively using an antireflection property according to optimizing the refractive index and absorbance of the underlayer hard mask, thereby securing a lithography process margin. It aims to do it.
그러므로 본 발명에서는 (a) 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물로부터 생성되는 중합체;Therefore, in the present invention (a) a polymer produced from the compound represented by the formula (1) and the compound represented by the formula (2);
(b) 화학식 3으로 표시되는 고분자;(b) a polymer represented by Formula 3;
(c) 산 또는 염기성 촉매 및(c) acid or basic catalysts and
유기용매로 이루어진 것을 특징으로 하는 레지스트 하층막용 하드마스크 조 성물이 제공된다.There is provided a hard mask composition for a resist underlayer film comprising an organic solvent.
[화학식 1][Formula 1]
(n은 3 ~ 20임.)(n is 3 to 20)
[화학식 2][Formula 2]
(R은 1가의 유기기를 나타내고, m은 0 내지 2의 정수임.)(R represents a monovalent organic group and m is an integer of 0 to 2.)
[화학식 3][Formula 3]
(상기 식에서, R1는
또한, 본 발명에서는 (a) 중합체 중 규소함유 단위의 총량을 기준으로 10~99몰%의 화학식 4의 반복단위 및 1~90몰%의 화학식 5또는 화학식 6중 적어도 하나의 반복단위를 포함하는 것을 특징으로 하는 중합체; (b) 화학식 3으로 표시되는 고분자; (c) 산 또는 염기성 촉매 및 유기용매로 이루어진 것을 특징으로 하는 레지스트 하층막용 하드마스크 조성물이 제공된다.In the present invention, (a) 10 to 99 mol% of the repeating unit of the formula (4) and 1 to 90 mol% of at least one repeating unit of the formula (5) or (6) based on the total amount of silicon-containing units in the polymer A polymer, characterized in that; (b) a polymer represented by Formula 3; (c) A hard mask composition for resist underlayer film comprising an acid or basic catalyst and an organic solvent is provided.
[화학식 4][Formula 4]
[화학식 5][Formula 5]
(R은 1가의 유기기)(R is a monovalent organic group)
[화학식 6][Formula 6]
(R1, R2는 1가의 유기기로 서로 같거나 다를 수 있다.)(R1, R2 may be the same or different from each other in monovalent organic group.)
상기 염기성 촉매로는 NH4OH 또는 NR4OH로 표시되는 암모늄 히드록사이드 중 선택되는 어느 하나(단, R은 1가의 유기기이다.)인 것을 특징으로 한다.The basic catalyst may be any one selected from ammonium hydroxide represented by NH 4 OH or NR 4 OH (where R is a monovalent organic group).
상기 산 촉매는 p-톨루엔 술폰산 모노 하이드레이트(p-toluenesulfonic acid mono hydrate), 피리딘 p-톨루엔술폰산(Pyridine p-toluenesulfonic acid), 2,4,4,6-테트라브로모시클로헥사디엔온, 벤조인 토실레이트, 2-니트로벤질 토실레이트 및 유기 술폰산의 다른 알킬 에스테르로 이루어진 군에서 선택되는 어느 하나인 것을 특징으로 한다.The acid catalyst is p-toluenesulfonic acid mono hydrate, pyridine p-toluenesulfonic acid, 2,4,4,6-tetrabromocyclohexadienone, benzoin It is characterized in that it is any one selected from the group consisting of tosylate, 2-nitrobenzyl tosylate and other alkyl esters of organic sulfonic acid.
상기 중합체가 전체 조성에 대해 1~50중량% 포함된 것을 특징으로 한다.The polymer is characterized in that it contains 1 to 50% by weight based on the total composition.
상기 화학식 3으로 표시되는 고분자가 전체 조성에 대해 1~30 중량% 포함된 것을 특징으로 한다. It is characterized in that the polymer represented by the formula (3) contained 1 to 30% by weight based on the total composition.
상기 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 혼합해서 생성되는 중합체는 하기 화학식 7, 화학식8, 화학식9 및 화학식 10 중 적어도 하나의 구조를 갖는 것을 특징으로 한다.The polymer produced by mixing the compound represented by the formula (1) and the compound represented by the formula (2) is characterized by having a structure of at least one of the following formula 7, formula (8), formula (9) and formula (10).
[화학식 7][Formula 7]
[화학식 8][Formula 8]
(R은 1가의 유기기를 나타내며, m은 0내지 2의 정수임)(R represents a monovalent organic group, m is an integer from 0 to 2)
[화학식 9][Formula 9]
(R은 1가의 유기기이고, x는 10~99몰%이며 y는 1~90몰%이다.) (R is a monovalent organic group, x is 10-99 mol% and y is 1-90 mol%.)
[화학식 10][Formula 10]
(R은 1가의 유기기이고, x는 10~99몰%이며 y는 1~90몰%이다.) (R is a monovalent organic group, x is 10-99 mol% and y is 1-90 mol%.)
상기 조성물은 추가로 가교제 또는 계면활성제를 포함하는 것을 특징으로 한다.The composition is further characterized as comprising a crosslinking agent or a surfactant.
또한, 본 발명에서는 상기 레지스트 하층막용 하드마스크 조성물을 이용하여다음의 반도체 집적회로 디바이스의 제조방법을 제공할 수 있다In the present invention, the following method for manufacturing a semiconductor integrated circuit device can be provided using the hard mask composition for resist underlayer film.
(a) 기판 상에 재료 층을 제공하는 단계;(a) providing a layer of material on the substrate;
(b) 재료 층 위로 유기물로 이루어진 하드마스크 층을 형성시키는 단계;(b) forming a hardmask layer of organic material over the material layer;
(c) 재료 층 위로 레지스트 하층막용 하드마스크 조성물을 이용한 반사방지 하드마스크 층을 형성시키는 단계;(c) forming an antireflective hardmask layer using the hardmask composition for resist underlayer film over the material layer;
(d) 반사방지 하드마스크 층 위로 방사선-민감성 이미지화 층을 형성시키는 단계;(d) forming a radiation-sensitive imaging layer over the antireflective hardmask layer;
(e) 방사선-민감성 이미지화 층을 패턴 방식으로 방사선에 노출시킴으로써 이미지화 층 내에서 방사선-노출된 영역의 패턴을 생성시키는 단계;(e) generating a pattern of radiation-exposed regions within the imaging layer by exposing the radiation-sensitive imaging layer to radiation in a patterned manner;
(f) 방사선-민감성 이미지화 층 및 상기 반사방지 하드마스크 층의 부분을 선택적으로 제거하여 유기물 함유 하드마스크 재료 층의 부분을 노출시키는 단계; (f) selectively removing portions of the radiation-sensitive imaging layer and the antireflective hardmask layer to expose portions of the organic-containing hardmask material layer;
(g) 패턴화된 반사방지 하드마스크 층 및 유기물 함유 하드마스크 재료 층의 부분을 선택적으로 제거하여 재료층의 부분을 노출시키는 단계; 및(g) selectively removing portions of the patterned antireflective hardmask layer and the organic-containing hardmask material layer to expose portions of the material layer; And
(h) 재료 층의 노출된 부분을 에칭함으로써 패턴화된 재료 형상을 형성시키는 단계를 포함하는 것을 특징으로 하는 반도체 집적회로 디바이스의 제조방법.(h) forming a patterned material shape by etching the exposed portion of the material layer.
또한, 본 발명에서는 상기 방법에 의해 형성되는 것을 특징으로 하는 반도체 집적회로 디바이스가 제공된다.In addition, the present invention provides a semiconductor integrated circuit device formed by the above method.
이하 본 발명을 보다 상세히 설명하기로 한다.Hereinafter, the present invention will be described in more detail.
본 발명의 레지스트 하층막용 하드마스크 조성물은 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 혼합해서 생성되는 가수분해물 중합체, 화학식 3으로 표시되는 고분자, 산 혹은 염기성 촉매 및 유기용매를 포함한다.The hard mask composition for a resist underlayer film of the present invention includes a hydrolyzate polymer produced by mixing a compound represented by the formula (1) and a compound represented by the formula (2), a polymer represented by the formula (3), an acid or basic catalyst, and an organic solvent.
[화학식 1][Formula 1]
(n은 3 ~ 20임.)(n is 3 to 20)
[화학식 2][Formula 2]
(R은 1가의 유기기를 나타내고, m은 0 내지 2의 정수임.)(R represents a monovalent organic group and m is an integer of 0 to 2.)
[화학식 3][Formula 3]
(상기 식에서, R1는
상기 화학식 1의 화합물은 미쯔비시사의 상품명 MS51(분자량 600) 혹은 MS56(분자량 1200)의 Silicate를 예로 들 수 있으며, 가수분해 및 축합반응을 통해 본 발명을 위한 수지를 생성시킬 수 있다. Si 함량을 조절함에 따라 상부 포토레지스트 층 및 하부 유기물로 이루어진 하드마스크 층 사이의 에칭 선택비를 부여할 수 있다.The compound of Formula 1 may include Silicate of Mitsubishi's trade name MS51 (molecular weight 600) or MS56 (molecular weight 1200), and may generate a resin for the present invention through hydrolysis and condensation reaction. By controlling the Si content, the etching selectivity between the upper photoresist layer and the hardmask layer consisting of the lower organic material can be imparted.
상기 화학식 2의 화합물은 페닐트리메톡시실란이다. 본 물질에 포함하는 페닐그룹은 DUV 영역에서 흡수스펙트럼을 나타내는 점을 활용하여 반사방지 특성이 높은 재료를 제공함과 동시에 Ph-기의 농도비를 조절함으로써 특정 파장에서 원하는 흡수도와 굴절률을 가진 하드마스크 조성물을 제공할 수 있다.The compound of Formula 2 is phenyltrimethoxysilane. The phenyl group included in the present material provides a material having high anti-reflective properties by utilizing the point of absorption spectrum in the DUV region, and at the same time, adjusts the concentration ratio of the Ph-group to obtain a hard mask composition having a desired absorption and refractive index at a specific wavelength. Can provide.
상기 화학식 3의 화합물은 안트라센 함유 아크릴 공중합체이다. 본 물질에 포함하는 나프탈렌은 DUV 영역에서 흡수스펙트럼을 나타낼 뿐 아니라, 본 화합물의 첨가량에 따라 특정 두께에서 최적 굴절율 및 흡수도를 제공할 수 있다.The compound of formula 3 is an anthracene-containing acrylic copolymer. Naphthalene included in the present material not only exhibits an absorption spectrum in the DUV region, but may also provide an optimum refractive index and absorbance at a specific thickness depending on the amount of the present compound added.
상기 산 촉매는 p-톨루엔 술폰산 모노 하이드레이트(p-toluenesulfonic acid mono hydrate), 피리딘 p-톨루엔술폰산(Pyridine p-toluenesulfonic acid), 2,4,4,6-테트라브로모시클로헥사디엔온, 벤조인 토실레이트, 2-니트로벤질 토실레이트 및 유기 술폰산의 다른 알킬 에스테르로 이루어진 군에서 선택되는 어느 하나인 것이 바람직하다. The acid catalyst is p-toluenesulfonic acid mono hydrate, pyridine p-toluenesulfonic acid, 2,4,4,6-tetrabromocyclohexadienone, benzoin It is preferably one selected from the group consisting of tosylate, 2-nitrobenzyl tosylate and other alkyl esters of organic sulfonic acids.
또한, 상기 염기성 촉매는 NH4OH 또는 NR4OH로 표시되는 암모늄 히드록사이드 중 선택되는 어느 하나인 것이 바람직하다.(단, R은 1가의 유기기이다.)In addition, the basic catalyst is preferably any one selected from ammonium hydroxide represented by NH 4 OH or NR 4 OH, provided that R is a monovalent organic group.
상기 산촉매 혹은 염기성촉매는 그 종류, 투입량 및 투입방법을 조절하여 수지 합성시 가수분해 혹은 축합반응을 적절히 제어할 수 있다.The acid catalyst or the basic catalyst can appropriately control the hydrolysis or condensation reaction in synthesizing the resin by adjusting the type, the amount and the method of addition.
또한, 본 발명의 다른 측면은, (a) 중합체 중 규소함유 단위의 총량을 기준으로 10~99몰%의 화학식 4의 반복단위 및 1~90몰%의 화학식 5또는 화학식 6중 적어도 하나의 반복단위를 포함하는 중합체, (b) 화학식 3으로 표시되는 고분자, (c) 산 혹은 염기성 촉매 및 유기용매로 이루어진 것을 특징으로 하는 레지스트 하층막용 하드마스크 조성물이 제공된다.Further, another aspect of the present invention, (a) 10 to 99 mole% of the repeating unit of formula 4 and 1 to 90 mole% of the repeating unit of formula 5 or formula 6 based on the total amount of silicon-containing units Provided is a hard mask composition for a resist underlayer film, comprising a polymer comprising a unit, (b) a polymer represented by the formula (3), (c) an acid or basic catalyst, and an organic solvent.
[화학식 4][Formula 4]
[화학식 5][Formula 5]
(R은 1가의 유기기)(R is a monovalent organic group)
[화학식 6][Formula 6]
(R1, R2는 1가의 유기기로 서로 같거나 다를 수 있다.)(R1, R2 may be the same or different from each other in monovalent organic group.)
본 발명에서 상기 하드마스크 조성물은 산 또는 염기성 촉매 하에서 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물로부터 생성되는 중합체 또는 화학식 4의 반복단위 및 화학식 5와 화학식 6의 반복단위 중 적어도 하나를 포함하는 중합체는 전체 조성에 대해 1~50 중량%인 것이 바람직하며, 보다 바람직하게는 1~30중량%를 포함한다. In the present invention, the hard mask composition includes at least one of a compound represented by Formula 1 and a compound represented by Formula 2 or a repeating unit of Formula 4 and a repeating unit of Formulas 5 and 6 under an acid or basic catalyst. The polymer is preferably 1 to 50% by weight, more preferably 1 to 30% by weight based on the total composition.
본 발명에서 상기 화학식 3으로 표시되는 고분자는 전체 조성에 대해 1 ~ 30 중량%를 포함한다.In the present invention, the polymer represented by Formula 3 includes 1 to 30% by weight based on the total composition.
본 발명에서 상기 유기용매는 단독 또는 2종 이상의 용매를 혼합하여 사용할 수 있으며, 적어도 하나는 고비등 용매를 사용한다. 고비등 용매는 보이드(Void)를 방지하며 , 필름을 저속도 건조화 함으로써 평탄성을 향상시킨다. 여기서, "고비등 용매"란 발명물질의 코팅, 건조, 그리고 경화시의 온도보다 좀 더 낮은 온도 근처에서 휘발하는 용매를 의미한다. In the present invention, the organic solvent may be used alone or in combination of two or more solvents, at least one of the high boiling solvent. High boiling solvent prevents voids and improves flatness by drying the film at low speed. Here, "high boiling solvent" means a solvent that volatilizes near a temperature lower than the temperature at the time of coating, drying and curing the invention.
본 발명에서 화학식 1의 화합물과 화학식 2의 화합물을 산 또는 염기성 촉매 하에서 반응하여 생성 된 중합체는 바람직하게 하기 화학식7, 화학식8, 화학식 9 및 화학식 10 중 적어도 하나의 구조를 갖는다.In the present invention, the polymer produced by reacting the compound of Formula 1 with the compound of Formula 2 under an acid or basic catalyst preferably has a structure of at least one of Formula 7, Formula 8, Formula 9 and Formula 10.
[화학식 7][Formula 7]
[화학식 8][Formula 8]
(R은 1가의 유기기를 나타내며, m은 0내지 2의 정수임)(R represents a monovalent organic group, m is an integer from 0 to 2)
[화학식 9][Formula 9]
(R은 1가의 유기기이고, x는 10~99몰%이며 y는 1~90몰%이다.) (R is a monovalent organic group, x is 10-99 mol% and y is 1-90 mol%.)
[화학식 10][Formula 10]
(R은 1가의 유기기이고, x는 10~99몰%이며 y는 1~90몰%이다.) (R is a monovalent organic group, x is 10-99 mol% and y is 1-90 mol%.)
본 발명에서 상기 조성물은 가교제 또는 계면활성제를 더 포함하는 것이 제공될 수 있다. In the present invention, the composition may be provided that further comprises a crosslinking agent or a surfactant.
또한, 본 발명에서는 (a) 기판 상에 재료 층을 제공하는 단계;In addition, the present invention provides a method for preparing a substrate comprising: (a) providing a material layer on a substrate;
(b) 재료 층 위로 유기물로 이루어진 하드마스크 층을 형성시키는 단계;(b) forming a hardmask layer of organic material over the material layer;
(c) 재료 층 위로 상기의 레지스트 하층막용 하드마스크 조성물을 이용한 반사방지 하드마스크 층을 형성시키는 단계;(c) forming an antireflective hardmask layer using the hardmask composition for resist underlayer film over the material layer;
(d) 반사방지 하드마스크 층 위로 방사선-민감성 이미지화 층을 형성시키는 단계;(d) forming a radiation-sensitive imaging layer over the antireflective hardmask layer;
(e) 방사선-민감성 이미지화 층을 패턴 방식으로 방사선에 노출시킴으로써 이미지화 층 내에서 방사선-노출된 영역의 패턴을 생성시키는 단계;(e) generating a pattern of radiation-exposed regions within the imaging layer by exposing the radiation-sensitive imaging layer to radiation in a patterned manner;
(f) 방사선-민감성 이미지화 층 및 상기 반사방지 하드마스크 층의 부분을 선택적으로 제거하여 유기물 함유 하드마스크 재료 층의 부분을 노출시키는 단계; (f) selectively removing portions of the radiation-sensitive imaging layer and the antireflective hardmask layer to expose portions of the organic-containing hardmask material layer;
(g) 패턴화된 반사방지 하드마스크 층 및 유기물 함유 하드마스크 재료 층의 부분을 선택적으로 제거하여 재료층의 부분을 노출시키는 단계; 및(g) selectively removing portions of the patterned antireflective hardmask layer and the organic-containing hardmask material layer to expose portions of the material layer; And
(h) 재료 층의 노출된 부분을 에칭함으로써 패턴화된 재료 형상을 형성시키는 단계를 포함하는 것을 특징으로 하는 반도체 집적회로 디바이스의 제조방법이 제공된다.(h) forming a patterned material shape by etching the exposed portion of the material layer.
상기 발명은 패터닝된 재료층 구조물, 예컨대 금속 와이어링 라인, 접촉공 또는 바이어스, 절연색션, 예컨대 다마스크 트렌치 또는 셀로우 트렌치 절연, 커패시터 구조물용 트렌치, 예컨대 집적 회로 장치의 설계에 사용될 수도 있는 것들을 형성하는데 사용할 수 있다. 상기 발명은 산화물, 질화물, 폴리실리콘 및 크롬의 패터닝된 층을 형성하는 것에 관하여 특히 유용하다.The invention forms patterned material layer structures, such as metal wiring lines, contact holes or vias, insulation sections such as damask trench or shallow trench isolation, trenches for capacitor structures, such as those that may be used in the design of integrated circuit devices. Can be used to The invention is particularly useful with regard to forming patterned layers of oxides, nitrides, polysilicones and chromium.
또한, 본 발명에서는 상기 제조방법에 의해 형성되는 것을 특징으로 하는 반도체 집적회로 디바이스가 제공된다.In addition, the present invention provides a semiconductor integrated circuit device, which is formed by the above manufacturing method.
이하, 실시예를 통하여 본 발명을 보다 구체적으로 설명하고자 하나, 이러한 실시예들은 단지 설명의 목적을 위한 것으로 본 발명을 제한하는 것으로 해석되어서는 안 된다.Hereinafter, the present invention will be described in more detail with reference to examples, but these examples are for illustrative purposes only and should not be construed as limiting the present invention.
[합성예 1]Synthesis Example 1
기계교반기, 냉각관, 1000ml 적가 깔대기, 질소가스 도입관을 구비한 1ℓ의 4구 플라스크에 메틸트리메톡시실란(methyltrimethoxysilane) 63.6g과 메틸실리케이트(methylsilicate:MS-56) 56.4g을 PGMEA 269g에 용해시킨 후, 용액 온도를 60℃로 유지하였다. 이어서 p-톨루엔술폰산모노하이드레이트(p-toluenesulfonic acid monohydrate) 1.2g을 용해시킨 이온교환수 47.4g을 1시간에 걸쳐 용액에 첨가하였다. 그후, 60도에서 4시간 반응시킨 후, 반응액을 실온까지 냉각하였다. 이 반응액으로부터 59.5g의 메탄올을 포함하는 PGMEA 용액을 제거하여 샘플을 얻었다.Dissolve 63.6 g of methyltrimethoxysilane and 56.4 g of methylsilicate (MS-56) in 269 g of PGMEA in a 1 liter four-necked flask equipped with a mechanical stirrer, cooling tube, 1000 ml dropping funnel and nitrogen gas introduction tube. After the solution was maintained at 60 ° C. Subsequently, 47.4 g of ion-exchanged water in which 1.2 g of p-toluenesulfonic acid monohydrate was dissolved was added to the solution over 1 hour. Then, after making it react for 4 hours at 60 degreeC, the reaction liquid was cooled to room temperature. The sample was obtained by removing the PGMEA solution containing 59.5g of methanol from this reaction liquid.
[합성예 2]Synthesis Example 2
기계교반기, 냉각관, 1000ml 적가 깔대기, 질소가스 도입관을 구비한 1ℓ의 4구 플라스크에 메틸트리메톡시실란(methyltrimethoxysilane) 29.6g과 페닐트리메톡시실란(phenyltrimethoxysilane) 3.96g과 메틸실리케이트(methylsilicate:MS-56) 26.4g을 PGMEA 134.6g에 용해시킨 후, 용액 온도를 60도로 유지하였다. 이어서 p-톨루엔술폰산모노하이드레이트(p-toluenesulfonic acid monohydrate) 0.6g을 용해시킨 이온교환수 23.2g을 1시간에 걸쳐 용액에 첨가하였다. 그후, 60도에서 4시간 반응시킨 후, 반응액을 실온까지 냉각하였다. 이 반응액으로부터 28.8g의 메탄올을 포함하는 PGMEA 용액을 제거하여 샘플을 얻었다.In a 1 liter four-necked flask equipped with a mechanical stirrer, a cooling tube, a 1000 ml dropping funnel and a nitrogen gas introduction tube, 29.6 g of methyltrimethoxysilane, 3.96 g of phenyltrimethoxysilane and methylsilicate MS-56) 26.4 g was dissolved in 134.6 g PGMEA, and then the solution temperature was maintained at 60 degrees. Subsequently, 23.2 g of ion-exchanged water in which 0.6 g of p-toluenesulfonic acid monohydrate was dissolved was added to the solution over 1 hour. Then, after making it react for 4 hours at 60 degreeC, the reaction liquid was cooled to room temperature. The sample was obtained by removing the PGMEA solution containing 28.8g of methanol from this reaction liquid.
[합성예 3]Synthesis Example 3
기계교반기, 냉각관, 1000ml 적가 깔대기, 질소가스 도입관을 구비한 1ℓ의 4구 플라스크에 메틸트리메톡시실란(methyltrimethoxysilane) 48.0g과 페닐트리메톡시실란(phenyltrimethoxysilane) 17.9g과 메틸실리케이트(methylsilicate:MS-56) 54.1g을 PGMEA 269.2g에 용해시킨 후, 용액 온도를 60도로 유지하였다. 이어서 p-톨루엔술폰산모노하이드레이트(p-toluenesulfonic acid monohydrate) 1.2g을 용해시킨 이온교환수 47.4g을 1시간에 걸쳐 용액에 첨가하였다. 그 후, 60도에서 4시간 반응시킨 후, 반응액을 실온까지 냉각하였다. 이 반응액으로부터 47.4g의 메탄올을 포함하는 PGMEA 용액을 제거하여 샘플을 얻었다.In a 1 liter four-necked flask equipped with a mechanical stirrer, a cooling tube, a 1000 ml dropping funnel and a nitrogen gas introduction tube, 48.0 g of methyltrimethoxysilane, 17.9 g of phenyltrimethoxysilane, and methylsilicate 54.1 g of MS-56) was dissolved in 269.2 g of PGMEA, and the solution temperature was maintained at 60 degrees. Subsequently, 47.4 g of ion-exchanged water in which 1.2 g of p-toluenesulfonic acid monohydrate was dissolved was added to the solution over 1 hour. Then, after making it react at 60 degree | times for 4 hours, the reaction liquid was cooled to room temperature. The PGMEA solution containing 47.4 g of methanol was removed from this reaction liquid, and the sample was obtained.
[합성예 4]Synthesis Example 4
기계교반기, 냉각관, 1000ml 적가 깔대기, 질소가스 도입관을 구비한 1ℓ의 4구 플라스크에 메틸트리메톡시실란(methyltrimethoxysilane) 30.3g과 프로필트리메톡시실란(propyltrimethoxysilane) 1.5g과 메틸실리케이트(methylsilicate:MS-56) 28.2g을 PGMEA 134g에 용해시킨 후, 용액 온도를 60도로 유지하였다. 이어서 p-톨루엔술폰산모노하이드레이트(p-toluenesulfonic acid monohydrate) 0.6g을 용해시킨 이온교환수 23.2g을 1시간에 걸쳐 용액에 첨가하였다. 그후, 60도에서 4시간 반응시킨 후, 반응액을 실온까지 냉각하였다. 이 반응액으로부터 31.3g의 메탄올을 포함하는 PGMEA 용액을 제거하여 샘플을 얻었다.In a 1 liter four-necked flask equipped with a mechanical stirrer, a cooling tube, a 1000 ml dropping funnel and a nitrogen gas introduction tube, 30.3 g of methyltrimethoxysilane, 1.5 g of propyltrimethoxysilane and methylsilicate MS-56) 28.2 g was dissolved in 134 g PGMEA, and then the solution temperature was maintained at 60 degrees. Subsequently, 23.2 g of ion-exchanged water in which 0.6 g of p-toluenesulfonic acid monohydrate was dissolved was added to the solution over 1 hour. Then, after making it react for 4 hours at 60 degreeC, the reaction liquid was cooled to room temperature. The sample was obtained by removing the PGMEA solution containing 31.3g of methanol from this reaction liquid.
[합성예 5]Synthesis Example 5
기계교반기, 냉각관, 300ml 적가 깔대기, 질소가스 도입관을 구비한 1ℓ의 4구 플라스크에 질소가스를 유입하면서 1,4-비스(메톡시메틸)벤젠(1,4-Bis(methoxymethyl)benzene) 8.31g(0.05몰)과 디에틸설페이트(Diethyl Sulfate) 0.154g(0.001몰)과 200g의 γ-부티로락톤을 담고 잘 저어주었다. 10분 후에 4,4'-(9-플루오레닐리덴)디페놀 28.02g (0.08몰)을 200g의 γ-부티로락톤에 녹인 용액을 30분간 천천히 적가한 다음, 12시간 동안 반응을 실시하였다. 반응종료 후 물을 사용하여 산을 제거한 후에 증발기로 농축하였다. 이어서 MAK와 메탄올을 사용하여 희석하고 15 중량% 농도의 MAK/메탄올=4/1(중량비)의 용액으로 조정하였다. 이 용액을 3ℓ 분액깔대기에 넣고, 이것에 n-헵탄을 첨가하여 모노머를 함유하는 저분자량체를 제거하여 목적하는 페놀수지(Mw=12,000, polydispersity=2.0, n=23)를 얻었다. 1,4-bis (methoxymethyl) benzene with nitrogen gas flowing into a 1 liter four-necked flask equipped with a mechanical stirrer, a cooling tube, a 300 ml dropping funnel, and a nitrogen gas introduction tube. Stir well with 8.31 g (0.05 mole), 0.154 g (0.001 mole) diethyl sulfate and 200 g of γ-butyrolactone. After 10 minutes, a solution of 28.02 g (0.08 mol) of 4,4 '-(9-fluorenylidene) diphenol in 200 g of γ-butyrolactone was slowly added dropwise for 30 minutes, followed by reaction for 12 hours. . After completion of the reaction, the acid was removed using water, and then concentrated by an evaporator. It was then diluted with MAK and methanol and adjusted to a solution of 15 wt% MAK / methanol = 4/1 (weight ratio). The solution was placed in a 3 L separatory funnel, and n-heptane was added thereto to remove the low molecular weight containing the monomer to obtain the desired phenol resin (Mw = 12,000, polydispersity = 2.0, n = 23).
[합성예 6]Synthesis Example 6
기계교반기, 냉각관, 질소가스 도입관을 구비한 1ℓ의 4구 플라스크에 질소가스를 유입하면서 안트라센메틸메타크릴레이트(Anthracene methyl methacrylate:AMMA) 100g (0.36몰), 메틸메타크릴레이트(Methylmethacrylate:MMA) 36.23g(0.36몰), 하이드록시메틸메타크릴레이트(Hydroxymethylmethacrylate) 62.8g(0.48몰), V65 1.5g 그리고 400g의 THF를 담고 70도 조건에서 6시간 동안 반응을 실시하였다. 반응종료 후 반응용액을 12L Hexane에 적가하면서 침전시켰다. 침전된 폴리머는 깔대기를 사용하여 분리해 내고 진공오븐에서 72시간 동안 건조하여 목적하는 폴리머 (Mw=23,400, polydispersity=3.5, n=44)를 얻었다.100 g (0.36 mole) of anthracene methyl methacrylate (AMMA) and methyl methacrylate (Methyl methacrylate: MMA) while introducing nitrogen gas into a 1 L four-necked flask equipped with a mechanical stirrer, a cooling tube, and a nitrogen gas introduction tube. ) 36.23 g (0.36 mole), hydroxymethyl methacrylate (Hydroxymethylmethacrylate) 62.8 g (0.48 mole), V65 1.5 g and 400 g of THF was carried out for 6 hours at 70 degrees. After completion of the reaction, the reaction solution was precipitated dropwise into 12 L Hexane. The precipitated polymer was separated using a funnel and dried in a vacuum oven for 72 hours to obtain the desired polymer (Mw = 23,400, polydispersity = 3.5, n = 44).
[실시예 1]Example 1
합성예 1에서 만들어진 용액 48.12g에 합성예 6에서 얻어진 고분자 5g을 녹이고 추가로 PGMEA 131g과 시클로헥사논(Cyclohexanone)70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 48.12 g of the solution prepared in Synthesis Example 1, 5 g of the polymer obtained in Synthesis Example 6 was dissolved, and 131 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[실시예 2]Example 2
합성예 2에서 만들어진 용액 48.12g에 합성예6에서 얻어진 고분자 5g을 녹이고 추가로 PGMEA 131g과 시클로헥사논(Cyclohexanone) 70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 48.12 g of the solution prepared in Synthesis Example 2, 5 g of the polymer obtained in Synthesis Example 6 was dissolved, and 131 g of PGMEA and 70.5 g of cyclohexanone were added to make a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[실시예 3]Example 3
합성예 3에서 만들어진 용액 48.12g에 합성예 6에서 얻어진 고분자 5g을 녹이고 추가로 PGMEA 131g과 시클로헥사논(Cyclohexanone)70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 48.12 g of the solution prepared in Synthesis Example 3, 5 g of the polymer obtained in Synthesis Example 6 was dissolved, and 131 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[실시예 4]Example 4
합성예 4에서 만들어진 용액 48.12g에 합성예 6에서 얻어진 고분자 5g을 녹이고 추가로 PGMEA 131g과 시클로헥사논(Cyclohexanone)70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 48.12 g of the solution prepared in Synthesis Example 4, 5 g of the polymer obtained in Synthesis Example 6 was dissolved, and 131 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[비교예 1]Comparative Example 1
합성예 6에서 만들어진 고분자 0.8g과 아래의 구조단위의 반복으로 이루어진 올리고머 상태인 가교제(Powderlink 1174) 0.2g과 피리디늄 P-톨루엔 술포네이트(Pyridinium P-toluene sulfonate) 2mg을 PGMEA 9g에 넣어서 녹인 후 여과하여 샘플용액을 만들었다.0.8 g of the polymer prepared in Synthesis Example 6 and 0.2 g of a crosslinking agent (Powderlink 1174), which is composed of the following structural units, and 2 mg of pyridinium P-toluene sulfonate were dissolved in PGMEA 9 g. Filtration made a sample solution.
Powderlink 1174 구조Powderlink 1174 structure
[비교예 2]Comparative Example 2
합성예 1에서 만들어진 용액 48.12g에 PGMEA 131g과 시클로헥사논(Cyclohexanone)70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 48.12 g of the solution prepared in Synthesis Example 1, 131 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[비교예 3]Comparative Example 3
합성예 2에서 만들어진 용액 48.12g에 PGMEA 131g과 시클로헥사논(Cyclohexanone)70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 48.12 g of the solution prepared in Synthesis Example 2, 131 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[비교예 4][Comparative Example 4]
합성예 3에서 만들어진 용액 49.10g에 PGMEA 130g과 시클로헥사논(Cyclohexanone)70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 49.10 g of the solution prepared in Synthesis Example 3, 130 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
[비교예 5][Comparative Example 5]
합성예 4에서 만들어진 용액 47.34g에 PGMEA 132g과 시클로헥사논(Cyclohexanone) 70.5g을 넣어 희석용액을 만든다. 이 용액에 10wt% 피리딘(Pyridine)용액(용매 PGMEA) 0.624g을 넣어 최종 샘플 용액을 만든다.In 47.34 g of the solution prepared in Synthesis Example 4, 132 g of PGMEA and 70.5 g of cyclohexanone were added to form a dilute solution. 0.624 g of 10 wt% Pyridine solution (solvent PGMEA) was added to this solution to form a final sample solution.
실시예 1-4, 비교예 1-5 에서 만들어진 샘플을 실리콘웨이퍼에 스핀-코팅법으로 코팅하여 60초간 200℃에서 구워서 두께 1000Å의 필름을 형성시켰다.The samples made in Example 1-4 and Comparative Example 1-5 were coated on a silicon wafer by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1000 Å.
상기 필름들에 대한 굴절률(refractive index) n과 흡광계수(extinction coefficient) k를 구하였다. 사용기기는 Ellipsometer(J. A. Woollam 사)이고 측정결과는 표 1과 같다.The refractive index n and extinction coefficient k for the films were obtained. The instrument used was Ellipsometer (J. A. Woollam) and the measurement results are shown in Table 1.
합성예 5에서 만들어진 고분자 0.8g과 아래의 구조단위의 반복으로 이루어진 올리고머 상태인 가교제(Powderlink 1174) 0.2g과 피리디늄 P-톨루엔 술포네이트(Pyridinium P-toluene sulfonate) 2mg을 PGMEA 9g에 넣어서 녹인 후 여과하여 샘플용액을 만들었다. 0.8 g of the polymer produced in Synthesis Example 5 and 0.2 g of a crosslinking agent (Powderlink 1174), which is composed of the following structural units, and 2 mg of pyridinium P-toluene sulfonate were dissolved in PGMEA 9 g. Filtration made a sample solution.
이 샘플을 실리콘웨이퍼에 스핀-코팅법으로 코팅하여 60초간 200℃에서 구워서 두께 5000Å의 필름을 형성시켰다. The sample was coated on a silicon wafer by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 5000 mm 3.
실시예 1-4과 비교예 2-5에서 만들어진 샘플을 상기 제조된 웨이퍼 위에 스핀-코팅법으로 코팅하여 60초간 200℃에서 구워서 두께 1500Å의 필름을 형성시켰다. 제조된 필름위에 KrF용 포토레지스트를 코팅하고 110℃에서 60초간 굽고 ASML(XT:1400, NA 0.93)사의 노광장비를 사용해 노광을 한 다음 TMAH(2.38wt% 수용액)으로 현상하였다. 그리고 FE-SEM을 사용하여 90㎚의 라인 앤드 스페이스(line and space) 패턴을 고찰한 결과 하기 표 2와 같은 결과를 얻었다. 노광량의 변화에 따른 EL(expose latitude) 마진(margine)과 광원과의 거리변동에 따른 DoF(depth of focus) 마진(margine)을 고찰하여 표 2에 기록하였다. Samples made in Examples 1-4 and Comparative Examples 2-5 were coated on the wafer thus prepared by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1500 Å. A photoresist for KrF was coated on the prepared film, baked at 110 ° C. for 60 seconds, exposed to light using an exposure equipment of ASML (XT: 1400, NA 0.93), and developed with TMAH (2.38 wt% aqueous solution). And using a FE-SEM to examine the line and space (line and space) pattern of 90nm as shown in Table 2 below. The exposure latitude (EL) margin according to the change of the exposure dose and the depth of focus (DoF) margin according to the distance change with the light source are considered and recorded in Table 2.
패턴화된 시편을 CHF3/CF4 혼합가스를 사용하여 드라이 에칭을 진행하고 이어서 산소가 포함된 CHF3/CF4 혼합가스를 사용하여 다시 드라이 에칭을 진행한 다음, 마지막으로 BCl3/Cl2 혼합가스를 사용하여 드라이 에칭을 진행하였다. 마지막으로 O2가스를 사용하여 남아 있는 유기물을 모두 제거한 다음, FE SEM으로 단면을 고찰하여 표 3에 결과를 수록하였다.A patterned specimen by CHF 3 / CF 4, using a gas mixture the progress of dry etching, followed by including the oxygen CHF 3 / CF 4 used a mixed gas proceeding dry etching back, and then, finally, BCl 3 / Cl 2 Dry etching was performed using the mixed gas. Finally, after removing all remaining organics using O 2 gas, the cross section was examined by FE SEM and the results are listed in Table 3.
합성예 5에서 만들어진 고분자 0.8g과 아래의 구조단위의 반복으로 이루어진 올리고머 상태인 가교제(Powderlink 1174) 0.2g과 피리디늄 P-톨루엔 술포네이트(Pyridinium P-toluene sulfonate) 2mg을 PGMEA 9g에 넣어서 녹인 후 여과하여 샘플용액을 만들었다. 이 샘플을 실리콘웨이퍼에 스핀-코팅법으로 코팅하여 60초간 200℃에서 구워서 두께 5000Å의 필름을 형성시켰다. 실시예 1-4과 비교예 2-5에서 만들어진 샘플을 상기 제조된 웨이퍼 위에 스핀-코팅법으로 코팅하여 60초간 200℃에서 구워서 두께 1500Å의 필름을 형성시켰다. 제조된 필름위에 ArF용 포토레지스트를 코팅하고 110℃에서 60초간 굽고 ArF 노광장비인 ASML1250 (FN70 5.0 active, NA 0.82)를 사용해 노광을 한 다음 TMAH(2.38wt% 수용액)으로 현상하였다. 그리고 FE-SEM을 사용하여 80㎚의 라인 앤드 스페이스(line and space) 패턴을 고찰한 결과 하기 표 4와 같은 결과를 얻었다. 노광량의 변화에 따른 EL(expose latitude) 마진(margine)과 광원과의 거리변동에 따른 DoF(depth of focus) 마진(margine)을 고찰하여 표 4에 기록하였다.0.8 g of the polymer produced in Synthesis Example 5 and 0.2 g of a crosslinking agent (Powderlink 1174), which is composed of the following structural units, and 2 mg of pyridinium P-toluene sulfonate were dissolved in PGMEA 9 g. Filtration made a sample solution. The sample was coated on a silicon wafer by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 5000 mm 3. Samples made in Examples 1-4 and Comparative Examples 2-5 were coated on the wafer thus prepared by spin-coating to bake at 200 ° C. for 60 seconds to form a film having a thickness of 1500 Å. The ArF photoresist was coated on the prepared film, baked at 110 ° C. for 60 seconds, exposed to light using an ArF exposure equipment, ASML1250 (FN70 5.0 active, NA 0.82), and developed with TMAH (2.38 wt% aqueous solution). And using a FE-SEM to examine the line and space (line and space) pattern of 80nm as shown in Table 4 below. The exposure latitude (EL) margin according to the change in the exposure dose and the depth of focus (DoF) margin according to the distance change with the light source were considered and recorded in Table 4.
상기 표 4의 패턴화된 시편을 CHF3/CF4 혼합가스를 사용하여 드라이 에칭을 진행하고 이어서 산소가 포함된 CHF3/CF4 혼합가스를 사용하여 다시 드라이 에칭을 진행한 다음, CHF3/CF4 혼합가스를 사용하여 드라이 에칭을 다시 진행하였다. 마지막으로 O2가스를 사용하여 남아 있는 유기물을 모두 제거한 다음, FE SEM으로 단면을 고찰하여 표 5에 결과를 수록하였다.The patterned specimens of Table 4 CHF 3 / CF 4 with a mixed gas proceeds to dry etching, and then proceeds to dry etching again using a CHF 3 / CF 4 gas mixture containing oxygen, and then, CHF 3 / Dry etching was again performed using a CF 4 mixed gas. Finally, after removing all remaining organics using O 2 gas, the cross section was examined by FE SEM and the results are listed in Table 5.
본 발명은 하층막용 하드마스크의 굴절율, 흡광도를 최적화 함에 따라 반사방지특성을 효과적으로 사용하여 이에 리쏘그래피 공정마진을 확보할수 있는 신규한 레지스트 하층막용 하드마스크 조성물을 제공할 수 있다.The present invention can provide a novel resist underlayer film hard mask composition capable of securing a lithography process margin by effectively using the antireflection property by optimizing the refractive index and the absorbance of the underlayer hard mask.
Claims (11)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020050130010A KR100713231B1 (en) | 2005-12-26 | 2005-12-26 | Hard mask composition for resist underlayer film and manufacturing method of semiconductor integrated circuit device using same |
| JP2006072742A JP4421566B2 (en) | 2005-12-26 | 2006-03-16 | Hard mask composition for photoresist underlayer film and method of manufacturing semiconductor integrated circuit device using the same |
| US11/507,701 US7514199B2 (en) | 2005-12-26 | 2006-08-22 | Hardmask compositions for resist underlayer film and method for producing semiconductor integrated circuit device using the same |
| TW095134014A TWI327680B (en) | 2005-12-26 | 2006-09-14 | Hardmask compositions for resist underlayer film and method for producing semiconductor integrated circuit device using the same |
| CN2006101504434A CN1991581B (en) | 2005-12-26 | 2006-10-27 | Hardmask composition coated under photoresist and process of producing integrated circuit devices using thereof |
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| KR1020050130010A KR100713231B1 (en) | 2005-12-26 | 2005-12-26 | Hard mask composition for resist underlayer film and manufacturing method of semiconductor integrated circuit device using same |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008150058A1 (en) * | 2007-06-05 | 2008-12-11 | Cheil Industries Inc. | Hardmask composition having antireflective properties and method of patterning material on substrate using the same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4786636B2 (en) * | 2007-12-26 | 2011-10-05 | Ａｚエレクトロニックマテリアルズ株式会社 | Antireflection film forming composition and pattern forming method using the same |
| WO2013146670A1 (en) * | 2012-03-27 | 2013-10-03 | 日産化学工業株式会社 | Resist underlayer film-forming composition which contains phenylindole-containing novolac resin |
| KR101747230B1 (en) | 2013-02-21 | 2017-06-14 | 제일모직 주식회사 | Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition |
| US9296879B2 (en) * | 2013-09-03 | 2016-03-29 | Rohm And Haas Electronic Materials Llc | Hardmask |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010080815A (en) * | 2000-01-17 | 2001-08-25 | 윤종용 | Photosensitive polymer and chemically amplified type photoresist composition containing the same |
| KR20040084701A (en) * | 2003-03-24 | 2004-10-06 | 신에쓰 가가꾸 고교 가부시끼가이샤 | An Anti-Reflection Film Material and a Substrate Having an Anti-Reflection Film and a Method for Forming a Pattern |
| KR20050074962A (en) * | 2002-10-15 | 2005-07-19 | 브레우어 사이언스 인코포레이션 | Anti-reflective compositions comprising triazine compounds |
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| JP2003502449A (en) * | 1999-06-10 | 2003-01-21 | ハネウエル・インターナシヨナル・インコーポレーテツド | Spin-on glass anti-reflective coating for photolithography |
| EP1071121A1 (en) * | 1999-07-19 | 2001-01-24 | International Business Machines Corporation | Process for the formation of a collar oxide in a trench in a semiconductor substrate |
| JP2001166462A (en) * | 1999-12-10 | 2001-06-22 | Fuji Photo Film Co Ltd | Original plate of planographic printing plate |
| US6573196B1 (en) * | 2000-08-12 | 2003-06-03 | Applied Materials Inc. | Method of depositing organosilicate layers |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010080815A (en) * | 2000-01-17 | 2001-08-25 | 윤종용 | Photosensitive polymer and chemically amplified type photoresist composition containing the same |
| KR20050074962A (en) * | 2002-10-15 | 2005-07-19 | 브레우어 사이언스 인코포레이션 | Anti-reflective compositions comprising triazine compounds |
| KR20040084701A (en) * | 2003-03-24 | 2004-10-06 | 신에쓰 가가꾸 고교 가부시끼가이샤 | An Anti-Reflection Film Material and a Substrate Having an Anti-Reflection Film and a Method for Forming a Pattern |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008150058A1 (en) * | 2007-06-05 | 2008-12-11 | Cheil Industries Inc. | Hardmask composition having antireflective properties and method of patterning material on substrate using the same |
| KR100908601B1 (en) * | 2007-06-05 | 2009-07-21 | 제일모직주식회사 | Anti-reflective hard mask composition and patterning method of substrate material using same |
| US7981594B2 (en) | 2007-06-05 | 2011-07-19 | Cheil Industries, Inc. | Hardmask composition having antirelective properties and method of patterning material on susbstrate using the same |
| US8445187B2 (en) | 2007-06-05 | 2013-05-21 | Cheil Industries, Inc. | Hardmask composition having antireflective properties and method of patterning material on substrate using the same |
Also Published As
| Publication number | Publication date |
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| CN1991581B (en) | 2010-05-26 |
| CN1991581A (en) | 2007-07-04 |
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