KR100400296B1 - 신규의포토레지스트가교제및이를이용한포토레지스트조성물 - Google Patents
신규의포토레지스트가교제및이를이용한포토레지스트조성물 Download PDFInfo
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- KR100400296B1 KR100400296B1 KR10-1998-0051355A KR19980051355A KR100400296B1 KR 100400296 B1 KR100400296 B1 KR 100400296B1 KR 19980051355 A KR19980051355 A KR 19980051355A KR 100400296 B1 KR100400296 B1 KR 100400296B1
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- Prior art keywords
- photoresist
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- crosslinking agent
- poly
- triflate
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 239000004971 Cross linker Substances 0.000 title description 4
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 6
- 229920001577 copolymer Polymers 0.000 claims abstract description 3
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- OBWGMYALGNDUNM-UHFFFAOYSA-N 3,3-dimethoxyprop-1-ene Chemical compound COC(OC)C=C OBWGMYALGNDUNM-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 7
- MCIPQLOKVXSHTD-UHFFFAOYSA-N 3,3-diethoxyprop-1-ene Chemical compound CCOC(C=C)OCC MCIPQLOKVXSHTD-UHFFFAOYSA-N 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- -1 diphenyl iodo hexafluorophosphate Chemical compound 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- 239000012953 triphenylsulfonium Substances 0.000 claims description 5
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- PHSXOZKMZYKHLY-UHFFFAOYSA-N 2-hydroxyethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCO)CC1C=C2 PHSXOZKMZYKHLY-UHFFFAOYSA-N 0.000 claims description 3
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims description 3
- 229940000489 arsenate Drugs 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 claims description 3
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 2
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- CPNBXOGOMSMGCF-UHFFFAOYSA-N (4-tert-butyl-2,3-diphenylphenyl) trifluoromethanesulfonate Chemical compound C=1C=CC=CC=1C=1C(C(C)(C)C)=CC=C(OS(=O)(=O)C(F)(F)F)C=1C1=CC=CC=C1 CPNBXOGOMSMGCF-UHFFFAOYSA-N 0.000 claims 1
- VUBUXALTYMBEQO-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)C(F)(F)C(=O)C1=CC=CC=C1 VUBUXALTYMBEQO-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 238000000206 photolithography Methods 0.000 abstract description 5
- 238000010884 ion-beam technique Methods 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- JGEMYUOFGVHXKV-UPHRSURJSA-N malealdehyde Chemical compound O=C\C=C/C=O JGEMYUOFGVHXKV-UPHRSURJSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- ZLZZZUYVKRXMRS-UHFFFAOYSA-N (4-benzhydrylphenyl) trifluoromethanesulfonate Chemical compound O(S(=O)(=O)C(F)(F)F)C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 ZLZZZUYVKRXMRS-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- AKOJHIADVIWDJF-UHFFFAOYSA-N [F].[F].[F].[F].[F].[F].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [F].[F].[F].[F].[F].[F].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 AKOJHIADVIWDJF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—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
- G03F7/039—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
- G03F7/0395—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 a backbone with alicyclic moieties
-
- 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
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
-
- 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
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
Claims (16)
- 하기 화학식 1의 화합물의 호모중합체 또는 공중합체를 포함하는 것을 특징으로 하는 포토레지스트 가교제.<화학식 1>여기서, R1및 R2는 각각 탄소수 1 내지 10의 주쇄 혹은 측쇄 치환된 알킬이며, R3는 수소 혹은 메틸이다.
- 제 1 항에 있어서,상기 가교제는 하기 화학식 2 또는 화학식 3의 화합물인 것을 특징으로 하는 가교제.<화학식 2>여기서, R1및 R2는 각각 탄소수 1 내지 10의 주쇄 혹은 측쇄 치환된 알킬이며, R3및 R4는 각각 수소 혹은 메틸이고, a : b 는 10∼100몰% : 0∼90몰%이다.<화학식 3>여기서, R1및 R2는 각각 탄소수 1 내지 10의 주쇄 혹은 측쇄 치환된 알킬이며, R3는 수소 혹은 메틸이고, a : b 는 10∼90몰% : 10∼90몰%이다.
- 제 1 항에 있어서,상기 가교제는폴리(3,3-디메톡시프로펜);폴리(3,3-디에톡시프로펜);폴리(3,3-디메톡시프로펜/아크릴산);폴리(3,3-디에톡시프로펜/아크릴산);폴리(3,3-디메톡시프로펜/말레익안하이드라이드); 및폴리(3,3-디에톡시프로펜/말레익안하이드라이드)로 이루어진 군으로부터 선택된 것을 특징으로 하는 가교제.
- (i) 포토레지스트 수지와,(ⅱ) 제3항의 포토레지스트 가교제와,(ⅲ) 광산발생제와,(ⅳ) 유기용매를 포함하는 것을 특징으로 하는 포토레지스트 조성물.
- 제 4 항에 있어서,상기 포토레지스트 수지는 하이드록시 그룹(-OH)을 갖는 것을 특징으로 하는 포토레지스트 조성물.
- 제 4 항에 있어서,상기 포토레지스트 수지는 하기 화학식 12로 표시되는 폴리(바이사이클로[2.2.1]헵트-5-엔/2-하이 드록시에틸바이사이클로[2.2.1]헵트-5-엔 2-카르복실레이트/말레익안하이드라이드)인 것을 특징으로 하는 포토레지스트 조성물.<화학식 12>
- 제 4 항에 있어서,상기 광산발생제는 디페닐요도염 헥사플루오르포스페이트, 디페닐요도염 헥사플루오르 아르세네이트, 디페닐요도염 헥사플루오르 안티모네이트, 디페닐파라메톡시페닐 트리플레이트, 디페닐파라톨루에닐 트리플레이트, 디페닐파라이소부틸페닐 트리플레이트, 디페닐파라-t-부틸페닐 트리플레이트, 트리페닐설포늄 헥사플루오르 포스페이트, 트리페닐설포늄 헥사플루오르 아르세네이트, 트리페닐설포늄 헥사플루오르 안티모네이트, 트리페닐설포늄 트리플레이트 및 디부틸나프틸설포늄 트리플레이트로 이루어진 군으로부터 선택된 1 또는 2 이상인 것을 특징으로 하는 포토레지스트 조성물.
- 제 4 항에 있어서,상기 유기용매는 시클로헥사논, 메틸 3-메톡시프로피오네이트, 에틸 3-에톡시프로피오네이트 및 프로필렌글리콜 메틸에테르 아세테이트로 이루어진 군으로부터 선택된 것을 특징으로 하는 포토레지스트 조성물.
- (a) 제4항 기재의 조성물을 소정의 피식각층 상부에 도포하는 단계와,(b) 노광장치를 이용하여 상기 기판을 노광하는 단계와,(C) 상기 결과물을 현상하는 단계를 포함하는 것을 특징으로 하는 포토레지스트 패턴 형성방법.
- 제 9 항에 있어서,상기 노광장치는 ArF광(193nm), KrF광(248nm), E-빔, X-레이, EUV 및 DUV(deep ultra violet)로 이루어진 군으로부터 선택된 노광원을 사용하는 것을 특징으로 하는 방법.
- 제 9 항에 있어서,상기 현상 공정은 알칼리 현상액을 사용하여 수행하는 것을 특징으로 하는 방법.
- 제 11 항에 있어서,상기 알칼리 현상액은 2.38 중량% 또는 2.5 중량% TMAH 수용액인 것을 특징으로 하는 방법.
- 제 9 항에 있어서,상기 (b) 단계의 전 및/또는 후에 베이크 공정을 더 포함하는 것을 특징으로 하는 방법.
- 제 13 항에 있어서,상기 베이크 공정은 70 내지 200℃에서 1 내지 5분간 수행되는 것을 특징으로 하는 방법.
- 제 9 항에 있어서,상기 포토레지스트 패턴은 네가티브 패턴인 것을 특징으로 하는 방법.
- 제9항 기재의 방법에 의해 제조된 반도체 소자.
Priority Applications (10)
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KR10-1998-0051355A KR100400296B1 (ko) | 1998-11-27 | 1998-11-27 | 신규의포토레지스트가교제및이를이용한포토레지스트조성물 |
GB9927637A GB2344104B (en) | 1998-11-27 | 1999-11-24 | Photoresist composition comprising a cross-linker |
US09/448,916 US6368773B1 (en) | 1998-11-27 | 1999-11-24 | Photoresist cross-linker and photoresist composition comprising the same |
DE19956531A DE19956531A1 (de) | 1998-11-27 | 1999-11-24 | Vernetzer für ein Photoresist und diesen enthaltende Photoresistzusammensetzung |
CNB991258568A CN1163796C (zh) | 1998-11-27 | 1999-11-26 | 用于光致抗蚀剂的交联剂及含该交联剂的光致抗蚀剂组合物 |
TW088120825A TW459010B (en) | 1998-11-27 | 1999-11-26 | Cross-linker for photoresist, and photoresist composition comprising the same |
NL1013685A NL1013685C2 (nl) | 1998-11-27 | 1999-11-26 | Verknopingsmiddel voor fotolaklaag en fotolaklaagsamenstelling welke deze omvat. |
FR9914920A FR2786491B1 (fr) | 1998-11-27 | 1999-11-26 | Agent de reticulation pour photoresist, et composition de photoresist comprenant celui-ci |
IT1999TO001042A IT1308659B1 (it) | 1998-11-27 | 1999-11-26 | Reticolante per fotoresist e composizione fotoresist comprendente lostesso. |
JP33865999A JP4127941B2 (ja) | 1998-11-27 | 1999-11-29 | フォトレジスト組成物、フォトレジストパターン形成方法、及び、半導体素子の製造方法 |
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KR100533379B1 (ko) * | 1999-09-07 | 2005-12-06 | 주식회사 하이닉스반도체 | 유기 난반사 방지막용 조성물과 이의 제조방법 |
KR100574482B1 (ko) * | 1999-09-07 | 2006-04-27 | 주식회사 하이닉스반도체 | 유기 난반사 방지막용 조성물과 이의 제조방법 |
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KR100557608B1 (ko) * | 1999-02-10 | 2006-03-10 | 주식회사 하이닉스반도체 | 신규의 포토레지스트 가교제 및 이를 이용한 포토레지스트 조성물 |
KR100533361B1 (ko) * | 1999-08-23 | 2005-12-06 | 주식회사 하이닉스반도체 | 유기 난반사 방지막 중합체 및 그의 제조방법 |
KR100557585B1 (ko) * | 1999-10-29 | 2006-03-03 | 주식회사 하이닉스반도체 | 레지스트 플로우 공정용 포토레지스트 조성물 및 이를 이용한 컨택홀의 형성방법 |
KR100866748B1 (ko) * | 2007-01-05 | 2008-11-03 | 주식회사 하이닉스반도체 | 감광제 조성물 및 이를 이용한 패턴 형성방법 |
US7749680B2 (en) | 2007-01-05 | 2010-07-06 | Hynix Semiconductor Inc. | Photoresist composition and method for forming pattern of a semiconductor device |
CN113321663B (zh) * | 2021-06-23 | 2022-07-22 | 徐州博康信息化学品有限公司 | 一种由1,3二羟基丙酮二聚体合成的主链可降解型光刻胶树脂单体及其合成方法和应用 |
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KR100533379B1 (ko) * | 1999-09-07 | 2005-12-06 | 주식회사 하이닉스반도체 | 유기 난반사 방지막용 조성물과 이의 제조방법 |
KR100574482B1 (ko) * | 1999-09-07 | 2006-04-27 | 주식회사 하이닉스반도체 | 유기 난반사 방지막용 조성물과 이의 제조방법 |
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