JP2008521039A - 深紫外線（ｄｅｅｐｕｖ）用のフォトレジスト組成物及びその方法 - Google Patents
深紫外線（ｄｅｅｐｕｖ）用のフォトレジスト組成物及びその方法 Download PDFInfo
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- JP2008521039A JP2008521039A JP2007542163A JP2007542163A JP2008521039A JP 2008521039 A JP2008521039 A JP 2008521039A JP 2007542163 A JP2007542163 A JP 2007542163A JP 2007542163 A JP2007542163 A JP 2007542163A JP 2008521039 A JP2008521039 A JP 2008521039A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 119
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 108
- 239000002253 acid Substances 0.000 claims abstract description 68
- 230000002378 acidificating effect Effects 0.000 claims abstract description 27
- 150000003457 sulfones Chemical class 0.000 claims abstract description 26
- -1 cyclic acid anhydrides Chemical class 0.000 claims description 50
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001174 sulfone group Chemical group 0.000 claims description 24
- 238000000576 coating method Methods 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
- 238000000671 immersion lithography Methods 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 5
- 239000006117 anti-reflective coating Substances 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000001393 microlithography Methods 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 239000012670 alkaline solution Substances 0.000 abstract description 4
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 239000011941 photocatalyst Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 31
- 239000010408 film Substances 0.000 description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000005855 radiation Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 10
- 241000630665 Hada Species 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 7
- 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 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- PLVOEKQNBIXHDI-SBSPUUFOSA-N (2R)-2-amino-3-[(7-hydroxy-2-oxochromene-3-carbonyl)amino]propanoic acid hydrochloride Chemical compound Cl.N[C@H](CNC(=O)c1cc2ccc(O)cc2oc1=O)C(O)=O PLVOEKQNBIXHDI-SBSPUUFOSA-N 0.000 description 5
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000000686 lactone group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- OPCDJHPXERVGTM-UHFFFAOYSA-M (4-methoxy-3,5-dimethylphenyl)-dimethylsulfanium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound COC1=C(C)C=C([S+](C)C)C=C1C.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OPCDJHPXERVGTM-UHFFFAOYSA-M 0.000 description 3
- BJEWLOAZFAGNPE-UHFFFAOYSA-N 1-ethenylsulfonylethane Chemical compound CCS(=O)(=O)C=C BJEWLOAZFAGNPE-UHFFFAOYSA-N 0.000 description 3
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 150000002596 lactones Chemical group 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
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- 150000002848 norbornenes Chemical class 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011295 pitch Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- DKDKCSYKDZNMMA-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1(O)CC2(OC(=O)C=C)C3 DKDKCSYKDZNMMA-UHFFFAOYSA-N 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- GKELHXYNBNIXOX-XINBEAJESA-N ac1q7dgb Chemical compound C1C(C)(C(/C2)=N\O)CC3CC\C(=N/O)C1C32N1CCOCC1 GKELHXYNBNIXOX-XINBEAJESA-N 0.000 description 2
- 150000001241 acetals Chemical group 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 2
- LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical compound C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 description 2
- GNTFBMAGLFYMMZ-UHFFFAOYSA-N bicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CCC2 GNTFBMAGLFYMMZ-UHFFFAOYSA-N 0.000 description 2
- WMRPOCDOMSNXCQ-UHFFFAOYSA-N bicyclo[3.3.2]decane Chemical compound C1CCC2CCCC1CC2 WMRPOCDOMSNXCQ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 229940099352 cholate Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- HOKNTYWEKQQKGV-UHFFFAOYSA-N disulfonylmethane Chemical class O=S(=O)=C=S(=O)=O HOKNTYWEKQQKGV-UHFFFAOYSA-N 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical class C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
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- 229940070710 valerate Drugs 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- HUDHSZARDMJQOQ-UHFFFAOYSA-N (1-methylcyclohexyl) bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1(C)CCCCC1 HUDHSZARDMJQOQ-UHFFFAOYSA-N 0.000 description 1
- DCTVCFJTKSQXED-UHFFFAOYSA-N (2-ethyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(CC)(OC(=O)C(C)=C)C2C3 DCTVCFJTKSQXED-UHFFFAOYSA-N 0.000 description 1
- OJGSGTWNQWAFBE-UHFFFAOYSA-N (2-methyl-2-adamantyl) bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)C1C4CC(C=C4)C1)C2C3 OJGSGTWNQWAFBE-UHFFFAOYSA-N 0.000 description 1
- HFLCKUMNXPOLSN-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(OC(=O)C(=C)C)C3 HFLCKUMNXPOLSN-UHFFFAOYSA-N 0.000 description 1
- UGVRGVIRHLMDHI-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3(O)CC1(O)CC2(OC(=O)C=C)C3 UGVRGVIRHLMDHI-UHFFFAOYSA-N 0.000 description 1
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 1
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 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 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 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
- G03F7/039—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- 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
- Y10S430/106—Binder 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
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/994,745 US7537879B2 (en) | 2004-11-22 | 2004-11-22 | Photoresist composition for deep UV and process thereof |
| PCT/IB2005/003517 WO2006054173A1 (en) | 2004-11-22 | 2005-11-21 | Photoresist composition for deep uv and process thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008521039A true JP2008521039A (ja) | 2008-06-19 |
| JP2008521039A5 JP2008521039A5 (enExample) | 2009-01-08 |
Family
ID=35892397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007542163A Pending JP2008521039A (ja) | 2004-11-22 | 2005-11-21 | 深紫外線（ｄｅｅｐｕｖ）用のフォトレジスト組成物及びその方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7537879B2 (enExample) |
| EP (1) | EP1828843A1 (enExample) |
| JP (1) | JP2008521039A (enExample) |
| KR (1) | KR20070089182A (enExample) |
| CN (1) | CN101061434A (enExample) |
| TW (1) | TW200632554A (enExample) |
| WO (1) | WO2006054173A1 (enExample) |
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| JP2010164712A (ja) * | 2009-01-14 | 2010-07-29 | Tokyo Ohka Kogyo Co Ltd | レジスト組成物、レジストパターン形成方法、高分子化合物及び化合物 |
| JP2010170056A (ja) * | 2009-01-26 | 2010-08-05 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物及びそれを用いたレジストパターン形成方法、並びに高分子化合物 |
| JP2010210835A (ja) * | 2009-03-09 | 2010-09-24 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物及びレジストパターン形成方法 |
| JP2010210796A (ja) * | 2009-03-09 | 2010-09-24 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物、レジストパターン形成方法、高分子化合物、化合物 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10307396A (ja) * | 1997-05-06 | 1998-11-17 | Fuji Photo Film Co Ltd | 遠紫外線露光用ポジ型フォトレジスト組成物 |
| JP2000231194A (ja) * | 1998-12-07 | 2000-08-22 | Fuji Photo Film Co Ltd | ポジ型フォトレジスト組成物 |
| JP2002202606A (ja) * | 2000-12-28 | 2002-07-19 | Fuji Photo Film Co Ltd | 遠紫外線露光用ポジ型フォトレジスト組成物 |
| JP2003316007A (ja) * | 2002-04-26 | 2003-11-06 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
| JP2004002720A (ja) * | 2002-03-26 | 2004-01-08 | Shin Etsu Chem Co Ltd | 高分子化合物、レジスト材料及びパターン形成方法 |
| JP2004062045A (ja) * | 2002-07-31 | 2004-02-26 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
| JP2004083873A (ja) * | 2002-07-02 | 2004-03-18 | Shin Etsu Chem Co Ltd | 珪素含有高分子化合物、レジスト材料及びパターン形成方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4491628A (en) | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
| EP0440374B1 (en) | 1990-01-30 | 1997-04-16 | Wako Pure Chemical Industries Ltd | Chemical amplified resist material |
| US5843624A (en) | 1996-03-08 | 1998-12-01 | Lucent Technologies Inc. | Energy-sensitive resist material and a process for device fabrication using an energy-sensitive resist material |
| TW526390B (en) | 1997-06-26 | 2003-04-01 | Shinetsu Chemical Co | Resist compositions |
| EP1143299B1 (en) | 2000-04-04 | 2003-07-16 | Sumitomo Chemical Company, Limited | Chemically amplified positive resist composition |
| US6447980B1 (en) | 2000-07-19 | 2002-09-10 | Clariant Finance (Bvi) Limited | Photoresist composition for deep UV and process thereof |
| TWI264442B (en) * | 2002-03-25 | 2006-10-21 | Shinetsu Chemical Co | Novel esters, polymers, resist compositions and patterning process |
| TWI304412B (en) * | 2002-03-26 | 2008-12-21 | Shinetsu Chemical Co | Polymers, resist compositions andpatterning process |
| KR100955006B1 (ko) * | 2002-04-26 | 2010-04-27 | 후지필름 가부시키가이샤 | 포지티브 레지스트 조성물 |
| US6919161B2 (en) * | 2002-07-02 | 2005-07-19 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing polymer, resist composition and patterning process |
| JP4025683B2 (ja) * | 2003-05-09 | 2007-12-26 | 松下電器産業株式会社 | パターン形成方法及び露光装置 |
| JP2005049695A (ja) * | 2003-07-30 | 2005-02-24 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
| JP2005055697A (ja) * | 2003-08-05 | 2005-03-03 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
-
2004
- 2004-11-22 US US10/994,745 patent/US7537879B2/en not_active Expired - Fee Related
-
2005
- 2005-11-21 KR KR1020077013992A patent/KR20070089182A/ko not_active Ceased
- 2005-11-21 JP JP2007542163A patent/JP2008521039A/ja active Pending
- 2005-11-21 WO PCT/IB2005/003517 patent/WO2006054173A1/en not_active Ceased
- 2005-11-21 EP EP05808458A patent/EP1828843A1/en not_active Withdrawn
- 2005-11-21 CN CNA2005800399398A patent/CN101061434A/zh active Pending
- 2005-11-22 TW TW094141024A patent/TW200632554A/zh unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10307396A (ja) * | 1997-05-06 | 1998-11-17 | Fuji Photo Film Co Ltd | 遠紫外線露光用ポジ型フォトレジスト組成物 |
| JP2000231194A (ja) * | 1998-12-07 | 2000-08-22 | Fuji Photo Film Co Ltd | ポジ型フォトレジスト組成物 |
| JP2002202606A (ja) * | 2000-12-28 | 2002-07-19 | Fuji Photo Film Co Ltd | 遠紫外線露光用ポジ型フォトレジスト組成物 |
| JP2004002720A (ja) * | 2002-03-26 | 2004-01-08 | Shin Etsu Chem Co Ltd | 高分子化合物、レジスト材料及びパターン形成方法 |
| JP2003316007A (ja) * | 2002-04-26 | 2003-11-06 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
| JP2004083873A (ja) * | 2002-07-02 | 2004-03-18 | Shin Etsu Chem Co Ltd | 珪素含有高分子化合物、レジスト材料及びパターン形成方法 |
| JP2004062045A (ja) * | 2002-07-31 | 2004-02-26 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015135527A (ja) * | 2005-05-01 | 2015-07-27 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 液浸リソグラフィーのための組成物および方法 |
| US8541529B2 (en) | 2008-08-22 | 2013-09-24 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition, method of forming resist pattern, and polymeric compound |
| JP2010113334A (ja) * | 2008-10-07 | 2010-05-20 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物およびレジストパターン形成方法 |
| US8487056B2 (en) | 2008-12-04 | 2013-07-16 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and method of forming resist pattern |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20070089182A (ko) | 2007-08-30 |
| EP1828843A1 (en) | 2007-09-05 |
| US20060110677A1 (en) | 2006-05-25 |
| CN101061434A (zh) | 2007-10-24 |
| TW200632554A (en) | 2006-09-16 |
| WO2006054173A1 (en) | 2006-05-26 |
| US7537879B2 (en) | 2009-05-26 |
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