JP5008079B2 - 光結像性ポジ型底面反射防止膜 - Google Patents
光結像性ポジ型底面反射防止膜 Download PDFInfo
- Publication number
- JP5008079B2 JP5008079B2 JP2007504508A JP2007504508A JP5008079B2 JP 5008079 B2 JP5008079 B2 JP 5008079B2 JP 2007504508 A JP2007504508 A JP 2007504508A JP 2007504508 A JP2007504508 A JP 2007504508A JP 5008079 B2 JP5008079 B2 JP 5008079B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- composition
- antireflective coating
- photoresist
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002253 acid Substances 0.000 claims abstract description 93
- 239000006117 anti-reflective coating Substances 0.000 claims abstract description 83
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 229920000642 polymer Polymers 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 40
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 15
- 229920002120 photoresistant polymer Polymers 0.000 claims description 108
- 238000000576 coating method Methods 0.000 claims description 42
- 239000000758 substrate Substances 0.000 claims description 37
- -1 anthracyl group Chemical group 0.000 claims description 32
- 239000011248 coating agent Substances 0.000 claims description 32
- 239000010410 layer Substances 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 19
- 230000005855 radiation Effects 0.000 claims description 16
- 239000011324 bead Substances 0.000 claims description 14
- 238000011161 development Methods 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 239000012670 alkaline solution Substances 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 239000010408 film Substances 0.000 description 86
- 239000000243 solution Substances 0.000 description 35
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 27
- 235000012431 wafers Nutrition 0.000 description 27
- 239000002904 solvent Substances 0.000 description 24
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 16
- 230000003667 anti-reflective effect Effects 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 11
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 235000006408 oxalic acid Nutrition 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- 238000005530 etching Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 125000005591 trimellitate group Chemical group 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 5
- 238000001312 dry etching Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 239000004065 semiconductor 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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 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
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 2
- QNSQZQLPBWNYPX-UHFFFAOYSA-N 2,2-bis(4-ethenoxybutyl)hexanedioic acid Chemical compound C=COCCCCC(CCCC(=O)O)(CCCCOC=C)C(O)=O QNSQZQLPBWNYPX-UHFFFAOYSA-N 0.000 description 2
- UWQPDVZUOZVCBH-UHFFFAOYSA-N 2-diazonio-4-oxo-3h-naphthalen-1-olate Chemical class C1=CC=C2C(=O)C(=[N+]=[N-])CC(=O)C2=C1 UWQPDVZUOZVCBH-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- GOBHFCSJIPJXPJ-UHFFFAOYSA-N 4-hydroxy-2-methylidene-5-phenylpent-4-enoic acid Chemical compound OC(=O)C(=C)CC(O)=CC1=CC=CC=C1 GOBHFCSJIPJXPJ-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 229940109275 cyclamate Drugs 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-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
- 125000000524 functional group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical group [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 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
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- OHWZQGOJLRVRIW-UHFFFAOYSA-N (3-carbamoyloxy-4-methylphenyl) carbamate Chemical compound CC1=CC=C(OC(N)=O)C=C1OC(N)=O OHWZQGOJLRVRIW-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- VXDAHXIZHTXQAO-UHFFFAOYSA-N 1-[2-(2,4-dinitroanilino)phenyl]pyrrole-2,5-dione Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1N1C(=O)C=CC1=O VXDAHXIZHTXQAO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NMMXJQKTXREVGN-UHFFFAOYSA-N 2-(4-benzoyl-3-hydroxyphenoxy)ethyl prop-2-enoate Chemical compound OC1=CC(OCCOC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 NMMXJQKTXREVGN-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- ICSZTCCEEGHFBL-UHFFFAOYSA-N 2-hydroxy-4-[[n-(2-methylprop-2-enoyl)anilino]diazenyl]benzoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(=C)C)N=NC1=CC=C(C(O)=O)C(O)=C1 ICSZTCCEEGHFBL-UHFFFAOYSA-N 0.000 description 1
- ZWUWDFWEMWMTHX-UHFFFAOYSA-N 2-methoxybutyl acetate Chemical compound CCC(OC)COC(C)=O ZWUWDFWEMWMTHX-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
- BKMGLHQPYYCKPO-UHFFFAOYSA-N 2-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=CC=C1S BKMGLHQPYYCKPO-UHFFFAOYSA-N 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- JRJNSEMUYTUGLA-UHFFFAOYSA-N 3-phenoxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC1=CC=CC=C1 JRJNSEMUYTUGLA-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 241000428352 Amma Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- ZHWSWVMDWKGHES-UHFFFAOYSA-N C(=C)C=1C2=CC=CC=C2C=C2C=CC=CC12.C(C(=C)C)(=O)OCC=1C2=CC=CC=C2C=C2C=CC=CC12 Chemical compound C(=C)C=1C2=CC=CC=C2C=C2C=CC=CC12.C(C(=C)C)(=O)OCC=1C2=CC=CC=C2C=C2C=CC=CC12 ZHWSWVMDWKGHES-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 229910000676 Si alloy Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YFQMOOBSTQTIIE-UHFFFAOYSA-N [C-](S(=O)(=O)C(F)(F)F)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.C1(=CC=CC=C1)[I+]C1=CC=CC=C1 Chemical compound [C-](S(=O)(=O)C(F)(F)F)(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.C1(=CC=CC=C1)[I+]C1=CC=CC=C1 YFQMOOBSTQTIIE-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- XOYZYOURGXJJOC-UHFFFAOYSA-N bis(2-tert-butylphenyl)iodanium Chemical compound CC(C)(C)C1=CC=CC=C1[I+]C1=CC=CC=C1C(C)(C)C XOYZYOURGXJJOC-UHFFFAOYSA-N 0.000 description 1
- KZYBDOUJLUPBEH-UHFFFAOYSA-N bis(4-ethenoxybutyl) benzene-1,3-dicarboxylate Chemical compound C=COCCCCOC(=O)C1=CC=CC(C(=O)OCCCCOC=C)=C1 KZYBDOUJLUPBEH-UHFFFAOYSA-N 0.000 description 1
- XUEAJYHEEJKSLM-UHFFFAOYSA-N bis(4-ethenoxybutyl) butanedioate Chemical compound C=COCCCCOC(=O)CCC(=O)OCCCCOC=C XUEAJYHEEJKSLM-UHFFFAOYSA-N 0.000 description 1
- LBYUWLDBALFUSJ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane;triphenylsulfanium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1.FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F LBYUWLDBALFUSJ-UHFFFAOYSA-N 0.000 description 1
- AEIRDZABQGATLB-UHFFFAOYSA-N bis[[4-(ethenoxymethyl)cyclohexyl]methyl] benzene-1,3-dicarboxylate Chemical compound C1CC(COC=C)CCC1COC(=O)C1=CC=CC(C(=O)OCC2CCC(COC=C)CC2)=C1 AEIRDZABQGATLB-UHFFFAOYSA-N 0.000 description 1
- UXMIQRKJEOXQPO-UHFFFAOYSA-N bis[[4-(ethenoxymethyl)cyclohexyl]methyl] benzene-1,4-dicarboxylate Chemical compound C1CC(COC=C)CCC1COC(=O)C1=CC=C(C(=O)OCC2CCC(COC=C)CC2)C=C1 UXMIQRKJEOXQPO-UHFFFAOYSA-N 0.000 description 1
- SDNBHBGJJPWRJG-UHFFFAOYSA-N bis[[4-(ethenoxymethyl)cyclohexyl]methyl] pentanedioate Chemical compound C1CC(COC=C)CCC1COC(=O)CCCC(=O)OCC1CCC(COC=C)CC1 SDNBHBGJJPWRJG-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- ORPDKMPYOLFUBA-UHFFFAOYSA-M diphenyliodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ORPDKMPYOLFUBA-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XJTWZSZWOJKDJL-UHFFFAOYSA-N ethyl 2-hydroxy-4-[2-(2-methyl-3-phenylprop-2-enoyl)iminohydrazinyl]benzoate Chemical compound C1=C(O)C(C(=O)OCC)=CC=C1NN=NC(=O)C(C)=CC1=CC=CC=C1 XJTWZSZWOJKDJL-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical class OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 238000012634 optical imaging Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDTPTXSNPBAUHX-UHFFFAOYSA-M trimethylsulfanium;hydroxide Chemical compound [OH-].C[S+](C)C MDTPTXSNPBAUHX-UHFFFAOYSA-M 0.000 description 1
- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Images
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
- G03F7/09—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
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/115—Cationic or anionic
-
- 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
- Y10S438/00—Semiconductor device manufacturing: process
- Y10S438/942—Masking
- Y10S438/948—Radiation resist
- Y10S438/952—Utilizing antireflective layer
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)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Description
凝縮器、温度計、窒素ガス入口及び機械的攪拌機を備えた250ml四つ首フラスコに、9−アントラセンメタノールのメタクリレートエステル(AMMA)(4.2g)、4−アセトキシスチレン(13.8g)、アゾビスイソブチロニトリル(AIBN)(0.8g)、及びプロピレングリコールモノメチルエーテル(PGME)(50g)を加えた。溶液が得られ、これを15分間脱気した。次いで、この反応混合物を70℃に加熱し、そして窒素を流しながらこの温度で5時間攪拌した。重合完了後、得られた溶液を室温まで冷却し、そしてテトラメチルアンモニウムヒドロキシド(水中26重量%)溶液(7g)を加えた。反応温度を40℃に高めそしてこの温度に3時間維持して、その後、60℃に高めた。60℃で8時間加熱した後、反応混合物を室温まで冷却し、そして酢酸を用いて6のpHに酸性化した。得られたポリマーを、メタノール600ml中で析出させ、そして得られた固形物を濾過し、メタノール及び脱イオン水で洗浄し、次いで乾燥した。析出したポリマーを、PGME60g中で再溶解し、そして再びメタノール600ml中で析出させた。得られた固形物を濾過し、洗浄しそして減圧下に40℃で乾燥した。得られたポリマー(以下の構造式(I)で表されるポリマー)は、ポリスチレン標準を使用してゲル透過クロマトグラフィ(GPC)により測定して、12,800の重量平均分子量(Mw)及び5,400の数平均分子量(Mn)を有していた。
合成例1からの構造式(I)で表されるコポリマー(2.5g)、トリス(4−ビニルオキシブチル)トリメリテート(0.25g、Vectomer(R)5015、Aldrich社から入手可能)、及びトリフェニルスルホニウムノナフレート(0.05g)を、プロピレングリコールモノメチルエーテルアセテート(PGMEA)68g及びプロピレングリコールモノメチルエーテル(PGME)29g中に溶解して、反射防止膜組成物とした。この溶液を、0.1μmフィルターに通して濾過した。
合成例1からの構造式(I)で表されるコポリマー(3g)、ビス(4−ビニルオキシブチル)アジペート(0.4g、Vectomer(R)4060、Aldrich社から入手可能)、及びシュウ酸(0.01g)を、PGMEA67.6g及びPGME28.8g中に溶解して、反射防止膜組成物とした。この溶液を0.1μmフィルターに通して濾過した。
合成例2からの構造式(II)で表されるコポリマー(2.6g)、トリス(4−ビニルオキシブチル)トリメリテート(0.26g、Vectomer(R)5015、Aldrich社から入手可能)、及びトリフェニルスルホニウムノナフレート(0.05g)を、PGMEA68g及びPGME29g中に溶解して、反射防止膜組成物とした。この溶液を0.1μmフィルターに通した。
合成例1からの構造式(I)で表されるコポリマー(3g)、トリエチレングリコールジビニルエーテル(0.6g、RAPI-CURE(R) DVE-3、ISP社(日本)から入手可能)、及びシュウ酸(0.01g)を、PGMEA67.6g及びPGME28.8g中に攪拌しながら溶解して、反射防止膜組成物とした。この溶液を、0.1μmフィルターに通して濾過した。
合成例3からの構造式(III)で表されるコポリマー(4g)、トリス(4−ビニルオキシブチル)トリメリテート(0.5g、Vectomer(R)5015、Aldrich社から入手可能)、及びシュウ酸(0.02g)を、PGMEA70g及びPGME30g中に攪拌しながら溶解して反射防止膜組成物とした。この溶液を、0.1μmフィルターに通して濾過した。
合成例4からの構造式(IV)で表されるコポリマー(2g)、トリス(4−ビニルオキシブチル)トリメリテート(0.2g、Vectomer(R)5015、Aldrich社から入手可能)、及びシュウ酸(0.01g)を、PGMEA70g及びPGME30g中に攪拌しながら溶解して、反射防止膜組成物とした。この溶液を0.1μmフィルターに通して濾過した。
合成例5からの構造式(V)で表されるコポリマー(2g)、トリス(4−ビニルオキシブチル)トリメリテート(0.2g、Vectomer(R)5015、Aldrich社から入手可能)、及びシュウ酸(0.01g)を、PGMEA70g及びPGME30g中に攪拌しながら溶解して、反射防止膜組成物とした。この溶液を0.1μmフィルターに通して濾過した。
例1で調製した溶液を、2500rpmで60秒間、6インチシリコンウェハ上にスピンコートし、次いでホットプレートで170℃で90秒間ベーク処理して、硬化した反射防止膜層を形成した。J.A. Woollam companyまたはSopra corporation製の偏光解析器によって測定したこの塗膜の膜厚は、約700Åであった。このコーティングされたウェハを観察すると、コーティング工程中に反射防止膜上に形成されたエッジビーズは、30重量%PGMEA及び70重量%PGMEからなる混合物をエッジビーズ除去溶剤として用いて、シリコンウェハを裏面リンスすることによって簡単に除去できることが分かった。
例1〜4で調製した溶液を6インチシリコンウェハ上にスピンコートし、そして170℃で90秒間ベーク処理して、60ナノメータの厚さを得た。次いで、DUVフォトレジスト(AZ(R) DX6270P (Clariant (Japan) K. K.から入手可能))をその上にコーティングし、そして120℃で90秒間ソフトベーク処理して、0.45ミクロンの厚さを得た。これらのコーティングされたウェハを、Cannon FPA-3000 EX5 248 nmステッパを用いて像様露光した。これらの露光されたウェハを、130℃で90秒間、露光後ベーク処理し、その後、AZ(R)300 MIF現像剤(Clariant Corp.から入手可能な、2.38重量%テトラメチルアンモニウムヒドロキシド水溶液)を用いて60秒間パドル現像した。二次電子顕微鏡の結果は、22mJ/cm2では、0.20μm1:1密集ライン及び0.20μm孤立ラインの両方が、フォトレジスト層及び反射防止膜層の双方において完全に開いている(open)ことを示した。基材からの反射による明らかな定在波は、パターンプロフィル上には観察されなかった。
ポリ(ヒドロキシスチレン−メタクリレート)(55/45モル比)1.5g、シュウ酸/トリエチルアミン(1:1)0.075g、トリフェニルスルホニウムトリフレート0.06g、及びVectomerTM5015(Aldrich社から入手可能)0.225gを、乳酸エチル98.5g中に溶解してB.A.R.C.溶液を得た。この溶液を、0.2μmマイクロフィルターに通して濾過した。このB.A.R.C.膜は、J. A. Woollam WVASE VU-302 TM偏光解析器によって測定して、193nmにおいてそれぞれ1.59及び0.62の屈折率(n)及び吸光パラメータ(k)を示した。
ポリ(ヒドロキシスチレン−メタクリレート)(55/45モル比)0.075g、シアノ酢酸0.015g、及びVectomerTM5015(0.022g)をプロピレングリコールモノメチルエーテル8.0g中に溶解した。この溶液を0.2μmマイクロフィルターに通して濾過した。
例10からのB.A.R.C.溶液を、下塗りしたシリコンウェハ上にコーティングし、そして175℃で90秒間ベーク処理して499Åの膜厚を得た。このB.A.R.C.ウェハを、AZ(R) T430フォトレジスト(ニュージャージー州、ソマービル在のClariant Corp.から入手可能)でコーティングし、ホットプレート上で120℃で60秒間加熱して、116nmの膜厚を得た。このコーティングされたウェハを、像様露光のためのISI 193nmミニステッパを用いて露光した。次いで、この露光されたウェハを120℃で20秒間、露光後ベーク処理し、その後AZ(R) 300MIF現像剤を用いて23℃で30秒間パドル現像した。二次電子顕微鏡を用いて、0.35μmフォトレジスト/B.A.R.C.ライン(1:1)が21mJ/cm2の線量で得られたことが確認された。
Claims (13)
- 水性アルカリ性現像剤中で現像することが可能な光結像性ポジ型底面反射防止膜組成物であって、発色団基を有する少なくとも一種の繰り返し単位と、ヒドロキシル及び/またはカルボキシル基を有する少なくとも一種の繰り返し単位とを含んでなるポリマー、末端ビニルエーテル基を有する架橋剤、及び酸または熱酸発生剤を含み、更に光酸発生剤を含むかまたは含まず、ここで前記の酸、または熱酸発生剤から誘導される酸が、1.0を超えるpKaを有する、上記組成物。
- 発色団基がポリマーに化学的に結合しており、そして芳香族炭化水素環を含む基、置換されているかもしくは置換されていないフェニル基、置換されているかもしくは置換されていないアントラシル基、置換されているかもしくは置換されていないフェナントリル基、置換されているかもしくは置換されていないナフチル基、酸素、窒素、硫黄及びこれらの混合物から選択されるヘテロ原子を含む置換されているかもしくは置換されていない複素環式芳香族環から選択される、請求項1の組成物。
- ヒドロキシル及び/またはカルボキシル基を含む繰り返し単位が、アクリル酸、メタクリル酸、ビニルアルコール、ヒドロキシスチレン類、及びヒドロキシスチレンと1,1,1,3,3,3−ヘキサフルオロ−2−プロパノール含有ビニルモノマーとのコポリマーから選択されるモノマーから誘導される、請求項1の組成物。
- 水性アルカリ性現像剤中で現像することが可能な光結像性ポジ型底面反射防止膜組成物であって、
・発色団基を有する少なくとも一種の繰り返し単位と、ヒドロキシル及び/またはカルボキシル基を有する少なくとも一種の繰り返し単位とを含んでなるポリマー、末端ビニルエーテル基を有する架橋剤、及び酸または熱酸発生剤を含み、更に光酸発生剤を含むかまたは含まず、
・発色団基とヒドロキシル及び/またはカルボキシル基は同一の繰り返し単位中に存在し、
・更にここで、前記の酸、または熱酸発生剤から誘導される酸が、1.0を超えるpKaを有する、
上記組成物。 - 酸、または熱酸発生剤から誘導される酸が、220℃未満の温度で反射防止膜から除去されるものである、請求項1の組成物。
- 染料を更に含む、請求項1の組成物。
- 染料が、モノマー性染料、ポリマー性染料、及びモノマー性染料とポリマー性染料との混合物からなる群から選択される、請求項7の組成物。
- 反射防止膜層が、0.1〜1.0の範囲のk値を有する、請求項1の組成物。
- 反射防止膜層が、フォトレジストの厚さより薄い厚さを有する、請求項1の組成物。
- 光酸発生剤が、50nm〜450nmの範囲の化学線に感度を示すものである、請求項1の組成物。
- 次の段階、すなわち
a) 請求項1の光結像性底面反射防止膜組成物の塗膜を基材上に形成する段階、
b) 前記反射防止膜をベーク処理する段階、
c) 上面フォトレジスト層の塗膜を、上記底面塗膜の上に供する段階、
d) 上記フォトレジスト層及び底面反射防止膜層を、同じ波長の化学線で像様露光する段階、
e) 上記基材上の上記フォトレジスト層及び底面反射防止膜層を露光後ベーク処理する段階、及び
f) 上記フォトレジスト層及び底面反射防止膜層を水性アルカリ性溶液で現像する段階、
g) ここで、反射防止膜が、フォトレジスト層をコーティングする前のベーク処理段階の後で、有機溶剤及び水性アルカリ性溶液中に不溶性になり、そしてフォトレジスト層及び底面反射防止膜層の現像の前の化学線による露光の後で、水性アルカリ性溶液中に可溶性になること、
を含む、ポジ型の像を形成する方法。 - コーティングの後かつ反射防止膜組成物のベーク処理段階の前に、エッジビーズを除去する段階を更に含む、請求項12の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/808,884 | 2004-03-25 | ||
US10/808,884 US20050214674A1 (en) | 2004-03-25 | 2004-03-25 | Positive-working photoimageable bottom antireflective coating |
PCT/IB2005/000773 WO2005093513A2 (en) | 2004-03-25 | 2005-03-23 | Positive-working photoimageable bottom antireflective coating |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011059412A Division JP5019338B2 (ja) | 2004-03-25 | 2011-03-17 | 光結像性ポジ型底面反射防止膜 |
JP2012003737A Division JP5391462B2 (ja) | 2004-03-25 | 2012-01-12 | 光結像性ポジ型底面反射防止膜 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2008501985A JP2008501985A (ja) | 2008-01-24 |
JP2008501985A5 JP2008501985A5 (ja) | 2012-03-01 |
JP5008079B2 true JP5008079B2 (ja) | 2012-08-22 |
Family
ID=34962084
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007504508A Active JP5008079B2 (ja) | 2004-03-25 | 2005-03-23 | 光結像性ポジ型底面反射防止膜 |
JP2011059412A Active JP5019338B2 (ja) | 2004-03-25 | 2011-03-17 | 光結像性ポジ型底面反射防止膜 |
JP2012003737A Active JP5391462B2 (ja) | 2004-03-25 | 2012-01-12 | 光結像性ポジ型底面反射防止膜 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011059412A Active JP5019338B2 (ja) | 2004-03-25 | 2011-03-17 | 光結像性ポジ型底面反射防止膜 |
JP2012003737A Active JP5391462B2 (ja) | 2004-03-25 | 2012-01-12 | 光結像性ポジ型底面反射防止膜 |
Country Status (9)
Country | Link |
---|---|
US (3) | US20050214674A1 (ja) |
EP (1) | EP1738225B1 (ja) |
JP (3) | JP5008079B2 (ja) |
KR (2) | KR20120000111A (ja) |
CN (2) | CN1942826B (ja) |
MY (1) | MY147755A (ja) |
SG (2) | SG183654A1 (ja) |
TW (2) | TWI407259B (ja) |
WO (1) | WO2005093513A2 (ja) |
Families Citing this family (104)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050214674A1 (en) * | 2004-03-25 | 2005-09-29 | Yu Sui | Positive-working photoimageable bottom antireflective coating |
US20070207406A1 (en) * | 2004-04-29 | 2007-09-06 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
US20050255410A1 (en) * | 2004-04-29 | 2005-11-17 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
EP2866093A1 (en) * | 2004-05-14 | 2015-04-29 | Nissan Chemical Industries, Limited | Anti-reflective coating forming composition containing vinyl ether compound and polyimide |
US7297370B2 (en) * | 2004-12-22 | 2007-11-20 | General Electric Company | Curable encapsulant composition, device including same, and associated method |
US7816071B2 (en) * | 2005-02-10 | 2010-10-19 | Az Electronic Materials Usa Corp. | Process of imaging a photoresist with multiple antireflective coatings |
US7781149B2 (en) * | 2005-03-23 | 2010-08-24 | Asml Netherlands B.V. | Reduced pitch multiple exposure process |
KR100612947B1 (ko) * | 2005-06-30 | 2006-08-14 | 주식회사 하이닉스반도체 | 비대칭 스텝구조의 게이트를 구비하는 반도체소자의 제조방법 |
US7375172B2 (en) | 2005-07-06 | 2008-05-20 | International Business Machines Corporation | Underlayer compositions containing heterocyclic aromatic structures |
US8828651B2 (en) * | 2005-07-25 | 2014-09-09 | Nissan Chemical Industries, Ltd. | Positive-type photosensitive resin composition and cured film manufactured therefrom |
JP5112733B2 (ja) | 2006-04-11 | 2013-01-09 | 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. | フォトリソグラフィ用コーティング組成物 |
US7563563B2 (en) * | 2006-04-18 | 2009-07-21 | International Business Machines Corporation | Wet developable bottom antireflective coating composition and method for use thereof |
US20070298176A1 (en) | 2006-06-26 | 2007-12-27 | Dipietro Richard Anthony | Aromatic vinyl ether based reverse-tone step and flash imprint lithography |
US7754414B2 (en) * | 2006-07-12 | 2010-07-13 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
US7914974B2 (en) * | 2006-08-18 | 2011-03-29 | Brewer Science Inc. | Anti-reflective imaging layer for multiple patterning process |
US8178287B2 (en) * | 2006-09-08 | 2012-05-15 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist composition and method of forming a resist pattern |
JP2008066587A (ja) * | 2006-09-08 | 2008-03-21 | Toshiba Corp | パターン形成方法 |
JP5201813B2 (ja) * | 2006-09-15 | 2013-06-05 | Hoya株式会社 | マスクブランク及びマスクの製造方法 |
KR101366147B1 (ko) | 2006-12-13 | 2014-02-24 | 닛산 가가쿠 고교 가부시키 가이샤 | 저분자 용해 촉진제를 포함하는 레지스트 하층막 형성 조성물 |
US7759046B2 (en) * | 2006-12-20 | 2010-07-20 | Az Electronic Materials Usa Corp. | Antireflective coating compositions |
JP2008170515A (ja) * | 2007-01-09 | 2008-07-24 | Konica Minolta Holdings Inc | 表面処理材料、基板、基板表面の処理方法、薄膜トランジスタ及び半導体デバイスの製造方法 |
US7432191B1 (en) * | 2007-03-30 | 2008-10-07 | Tokyo Electron Limited | Method of forming a dual damascene structure utilizing a developable anti-reflective coating |
WO2008156680A1 (en) * | 2007-06-15 | 2008-12-24 | Sba Materials, Inc. | Low k dielectric |
US20090098490A1 (en) * | 2007-10-16 | 2009-04-16 | Victor Pham | Radiation-Sensitive, Wet Developable Bottom Antireflective Coating Compositions and Their Applications in Semiconductor Manufacturing |
US8088548B2 (en) * | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
CN101842414B (zh) * | 2007-10-30 | 2014-06-04 | 布鲁尔科技公司 | 可光成像的支化聚合物 |
EP2209839A1 (en) * | 2007-11-06 | 2010-07-28 | Braggone OY | Carbosilane polymer compositions for anti-reflective coatings |
US7976894B1 (en) * | 2007-11-13 | 2011-07-12 | Brewer Science Inc. | Materials with thermally reversible curing mechanism |
US8039201B2 (en) * | 2007-11-21 | 2011-10-18 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
KR101325848B1 (ko) * | 2007-12-14 | 2013-11-05 | 후지쯔 가부시끼가이샤 | 티오피란 유도체, 중합체, 및 레지스트 조성물, 및, 상기 레지스트 조성물을 이용한 반도체 장치의 제조 방법 |
CN101971102B (zh) | 2008-01-29 | 2012-12-12 | 布鲁尔科技公司 | 用来通过多次暗视场曝光对硬掩模进行图案化的在线法 |
US9638999B2 (en) * | 2008-02-22 | 2017-05-02 | Brewer Science Inc. | Dual-layer light-sensitive developer-soluble bottom anti-reflective coatings for 193-nm lithography |
JP5192277B2 (ja) * | 2008-04-14 | 2013-05-08 | シャープ株式会社 | 固体撮像装置の製造方法 |
DE112009000979B4 (de) * | 2008-04-23 | 2014-12-11 | Brewer Science, Inc. | Photoempfindliche Hartmaske für die Mikrolithographie |
US8455176B2 (en) * | 2008-11-12 | 2013-06-04 | Az Electronic Materials Usa Corp. | Coating composition |
US20100136477A1 (en) * | 2008-12-01 | 2010-06-03 | Ng Edward W | Photosensitive Composition |
US9640396B2 (en) | 2009-01-07 | 2017-05-02 | Brewer Science Inc. | Spin-on spacer materials for double- and triple-patterning lithography |
US8273997B2 (en) | 2009-01-16 | 2012-09-25 | The Boeing Company | Antireflective apparatus with anisotropic capacitive circuit analog sheets |
US8182978B2 (en) | 2009-02-02 | 2012-05-22 | International Business Machines Corporation | Developable bottom antireflective coating compositions especially suitable for ion implant applications |
EP2399169B1 (en) * | 2009-02-19 | 2019-04-17 | Brewer Science, Inc. | Acid-sensitive, developer-soluble bottom anti-reflective coatings |
JPWO2010104074A1 (ja) * | 2009-03-10 | 2012-09-13 | 日産化学工業株式会社 | 側鎖にアセタール構造を有するポリマーを含むレジスト下層膜形成組成物及びレジストパターンの形成方法 |
JP5229025B2 (ja) * | 2009-03-13 | 2013-07-03 | Jsr株式会社 | パターン形成方法及び平坦化膜形成用組成物 |
JP2010285403A (ja) * | 2009-06-15 | 2010-12-24 | Nissan Chem Ind Ltd | 架橋剤及び該架橋剤を含有するレジスト下層膜形成組成物 |
US8632948B2 (en) * | 2009-09-30 | 2014-01-21 | Az Electronic Materials Usa Corp. | Positive-working photoimageable bottom antireflective coating |
US20110086312A1 (en) * | 2009-10-09 | 2011-04-14 | Dammel Ralph R | Positive-Working Photoimageable Bottom Antireflective Coating |
KR101186674B1 (ko) * | 2009-11-30 | 2012-09-27 | 금호석유화학 주식회사 | 흡광제 및 이를 포함하는 유기 반사 방지막 조성물 |
WO2011074433A1 (ja) | 2009-12-16 | 2011-06-23 | 日産化学工業株式会社 | 感光性レジスト下層膜形成組成物 |
JP5708938B2 (ja) * | 2010-01-18 | 2015-04-30 | 日産化学工業株式会社 | 感光性レジスト下層膜形成組成物及びレジストパターンの形成方法 |
US8445181B2 (en) | 2010-06-03 | 2013-05-21 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
US8685615B2 (en) | 2010-06-17 | 2014-04-01 | Nissan Chemical Industries, Ltd. | Photosensitive resist underlayer film forming composition |
JP5534205B2 (ja) * | 2010-08-27 | 2014-06-25 | 日産化学工業株式会社 | 感光性レジスト下層膜形成組成物及びレジストパターンの形成方法 |
US20120122029A1 (en) * | 2010-11-11 | 2012-05-17 | Takanori Kudo | Underlayer Developable Coating Compositions and Processes Thereof |
JP5844613B2 (ja) * | 2010-11-17 | 2016-01-20 | 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 | 感光性コポリマーおよびフォトレジスト組成物 |
JP5884961B2 (ja) * | 2011-04-27 | 2016-03-15 | 日産化学工業株式会社 | 光ラジカル重合開始剤を含む感光性レジスト下層膜形成組成物 |
US8623589B2 (en) | 2011-06-06 | 2014-01-07 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions and processes thereof |
US8697336B2 (en) * | 2011-12-15 | 2014-04-15 | Az Electronic Materials Usa Corp. | Composition for forming a developable bottom antireflective coating |
JP5555732B2 (ja) * | 2012-02-29 | 2014-07-23 | 富士フイルム株式会社 | 感光性樹脂組成物、これを用いた硬化膜の製造方法、硬化膜、液晶表示装置および有機el表示装置 |
JP6449145B2 (ja) * | 2012-04-23 | 2019-01-09 | ブルーワー サイエンス アイ エヌ シー. | 感光性、現像液可溶性の底面反射防止膜材料 |
US8999624B2 (en) * | 2012-06-29 | 2015-04-07 | International Business Machines Corporation | Developable bottom antireflective coating composition and pattern forming method using thereof |
US8900797B2 (en) * | 2012-09-26 | 2014-12-02 | Az Electronic Materials (Luxembourg) S.A.R.L. | Developable bottom anti-reflective coating |
WO2014071090A1 (en) | 2012-10-31 | 2014-05-08 | Sba Materials, Inc. | Compositions of low-k dielectric sols containing nonmetallic catalysts |
US9017934B2 (en) | 2013-03-08 | 2015-04-28 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist defect reduction system and method |
JP5956370B2 (ja) * | 2013-03-12 | 2016-07-27 | 信越化学工業株式会社 | 珪素含有下層膜材料及びパターン形成方法 |
US9245751B2 (en) | 2013-03-12 | 2016-01-26 | Taiwan Semiconductor Manufacturing Company, Ltd. | Anti-reflective layer and method |
US9175173B2 (en) | 2013-03-12 | 2015-11-03 | Taiwan Semiconductor Manufacturing Company, Ltd. | Unlocking layer and method |
US9110376B2 (en) | 2013-03-12 | 2015-08-18 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist system and method |
US9354521B2 (en) | 2013-03-12 | 2016-05-31 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist system and method |
US9502231B2 (en) | 2013-03-12 | 2016-11-22 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist layer and method |
US9543147B2 (en) | 2013-03-12 | 2017-01-10 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist and method of manufacture |
US9256128B2 (en) | 2013-03-12 | 2016-02-09 | Taiwan Semiconductor Manufacturing Company, Ltd. | Method for manufacturing semiconductor device |
US8932799B2 (en) | 2013-03-12 | 2015-01-13 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist system and method |
US9117881B2 (en) | 2013-03-15 | 2015-08-25 | Taiwan Semiconductor Manufacturing Company, Ltd. | Conductive line system and process |
WO2014196509A1 (ja) | 2013-06-03 | 2014-12-11 | アーゼット・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | レジスト下層膜形成用組成物 |
JP6119667B2 (ja) | 2013-06-11 | 2017-04-26 | 信越化学工業株式会社 | 下層膜材料及びパターン形成方法 |
JP6119668B2 (ja) | 2013-06-11 | 2017-04-26 | 信越化学工業株式会社 | 下層膜材料及びパターン形成方法 |
JP6119669B2 (ja) | 2013-06-11 | 2017-04-26 | 信越化学工業株式会社 | 下層膜材料及びパターン形成方法 |
JP6135600B2 (ja) | 2013-06-11 | 2017-05-31 | 信越化学工業株式会社 | 下層膜材料及びパターン形成方法 |
US9341945B2 (en) | 2013-08-22 | 2016-05-17 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist and method of formation and use |
JP6255210B2 (ja) | 2013-10-24 | 2017-12-27 | アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | レジスト下層膜形成組成物 |
US10036953B2 (en) | 2013-11-08 | 2018-07-31 | Taiwan Semiconductor Manufacturing Company | Photoresist system and method |
US10095113B2 (en) | 2013-12-06 | 2018-10-09 | Taiwan Semiconductor Manufacturing Company | Photoresist and method |
US9761449B2 (en) | 2013-12-30 | 2017-09-12 | Taiwan Semiconductor Manufacturing Company, Ltd. | Gap filling materials and methods |
JP6267532B2 (ja) | 2014-02-14 | 2018-01-24 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
TWI575566B (zh) | 2014-02-24 | 2017-03-21 | 東京威力科創股份有限公司 | 與光敏化化學放大光阻化學品及程序一起使用的方法及技術 |
US10020195B2 (en) * | 2014-02-25 | 2018-07-10 | Tokyo Electron Limited | Chemical amplification methods and techniques for developable bottom anti-reflective coatings and dyed implant resists |
US9599896B2 (en) | 2014-03-14 | 2017-03-21 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist system and method |
US9581908B2 (en) | 2014-05-16 | 2017-02-28 | Taiwan Semiconductor Manufacturing Company, Ltd. | Photoresist and method |
US11092894B2 (en) * | 2014-12-31 | 2021-08-17 | Rohm And Haas Electronic Materials Korea Ltd. | Method for forming pattern using anti-reflective coating composition comprising photoacid generator |
US10082734B2 (en) * | 2015-02-13 | 2018-09-25 | Taiwan Semiconductor Manufacturing Company, Ltd. | Composition and method for lithography patterning |
WO2017094780A1 (ja) * | 2015-12-01 | 2017-06-08 | 日産化学工業株式会社 | インドロカルバゾールノボラック樹脂を含むレジスト下層膜形成組成物 |
US10048594B2 (en) | 2016-02-19 | 2018-08-14 | Tokyo Electron Limited | Photo-sensitized chemically amplified resist (PS-CAR) model calibration |
US10429745B2 (en) | 2016-02-19 | 2019-10-01 | Osaka University | Photo-sensitized chemically amplified resist (PS-CAR) simulation |
WO2017197288A1 (en) | 2016-05-13 | 2017-11-16 | Tokyo Electron Limited | Critical dimension control by use of a photo agent |
CN109313394B (zh) | 2016-05-13 | 2021-07-02 | 东京毅力科创株式会社 | 使用光敏化学品或光敏化学放大抗蚀剂的临界尺寸控制 |
JP2018112674A (ja) * | 2017-01-12 | 2018-07-19 | 株式会社ニコン | パターン形成方法 |
US10388510B2 (en) | 2018-01-12 | 2019-08-20 | International Business Machines Corporation | Wet strippable OPL using reversible UV crosslinking and de-crosslinking |
WO2019198700A1 (ja) | 2018-04-13 | 2019-10-17 | 日産化学株式会社 | 半導体基板用プライマーおよびパターン形成方法 |
KR20200114438A (ko) | 2019-03-28 | 2020-10-07 | 삼성전자주식회사 | 반사방지막 형성용 폴리머 및 조성물과 반사방지막을 이용하는 집적회로 소자의 제조 방법 |
WO2021034567A1 (en) | 2019-08-16 | 2021-02-25 | Tokyo Electron Limited | Method and process for stochastic driven defectivity healing |
CN111538210B (zh) * | 2020-05-26 | 2023-11-17 | 苏州理硕科技有限公司 | 一种正性光刻胶组合物和形成光刻胶图案的方法 |
CN114517043B (zh) * | 2022-01-27 | 2022-12-16 | 福建泓光半导体材料有限公司 | 含有有机刚性笼状化合物的底部抗反射涂料组合物及其制备方法和微电子结构的形成方法 |
CN117820910A (zh) * | 2022-06-30 | 2024-04-05 | 华为技术有限公司 | 涂层材料和集成电路及制备方法、电子设备 |
CN115403976B (zh) * | 2022-08-19 | 2023-04-18 | 嘉庚创新实验室 | 一种抗反射涂层组合物 |
CN115386081B (zh) * | 2022-09-01 | 2023-07-28 | 武汉大学 | 一种原位热交联反应构筑二阶非线性光学聚合物材料的方法 |
Family Cites Families (105)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1086279A (en) | 1964-12-25 | 1967-10-04 | Fuji Photo Film Co Ltd | Heat developable photographic copying material |
US4061465A (en) | 1976-04-02 | 1977-12-06 | The United States Of America As Represented By The Secretary Of Agriculture | Creasable durable press textiles from methylol reagents and half amides or half salts of dicarboxylic acids |
US4229274A (en) * | 1979-02-26 | 1980-10-21 | Ppg Industries, Inc. | Ultraviolet light curable compositions for producing coatings of low gloss |
JPS5647440A (en) | 1979-09-28 | 1981-04-30 | Japan Synthetic Rubber Co Ltd | Rubber composition having high elastic modulus |
US4388450A (en) * | 1981-03-13 | 1983-06-14 | General Electric Company | Aromatic polyvinyl ethers and heat curable molding compositions obtained therefrom |
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 |
US4910122A (en) * | 1982-09-30 | 1990-03-20 | Brewer Science, Inc. | Anti-reflective coating |
US4863827A (en) * | 1986-10-20 | 1989-09-05 | American Hoechst Corporation | Postive working multi-level photoresist |
US4845265A (en) * | 1988-02-29 | 1989-07-04 | Allied-Signal Inc. | Polyfunctional vinyl ether terminated ester oligomers |
DE3817012A1 (de) * | 1988-05-19 | 1989-11-30 | Basf Ag | Positiv und negativ arbeitende strahlungsempfindliche gemische sowie verfahren zur herstellung von reliefmustern |
DE3930086A1 (de) * | 1989-09-09 | 1991-03-21 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial |
DE3930087A1 (de) | 1989-09-09 | 1991-03-14 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial |
US5650261A (en) * | 1989-10-27 | 1997-07-22 | Rohm And Haas Company | Positive acting photoresist comprising a photoacid, a photobase and a film forming acid-hardening resin system |
US5114826A (en) * | 1989-12-28 | 1992-05-19 | Ibm Corporation | Photosensitive polyimide compositions |
EP0440374B1 (en) * | 1990-01-30 | 1997-04-16 | Wako Pure Chemical Industries Ltd | Chemical amplified resist material |
KR100189642B1 (ko) * | 1991-02-18 | 1999-06-01 | 디어터 크리스트 | 전자 부품 및 조립체를 피복시키거나 접착시키는 방법 |
DE4112967A1 (de) | 1991-04-20 | 1992-10-22 | Hoechst Ag | Substituierte 1-sulfonyloxy-2-pyridone, verfahren zu ihrer herstellung und ihre verwendung |
DE4125260A1 (de) * | 1991-07-31 | 1993-02-04 | Hoechst Ag | Oligomere verbindungen mit saeurelabilen schutzgruppen und damit hergestelltes positiv arbeitendes strahlungsempfindliches gemisch |
JP3000745B2 (ja) * | 1991-09-19 | 2000-01-17 | 富士通株式会社 | レジスト組成物とレジストパターンの形成方法 |
JP2694097B2 (ja) * | 1992-03-03 | 1997-12-24 | インターナショナル・ビジネス・マシーンズ・コーポレイション | 反射防止コーティング組成物 |
US5362608A (en) | 1992-08-24 | 1994-11-08 | Brewer Science, Inc. | Microlithographic substrate cleaning and compositions therefor |
DE4302681A1 (de) * | 1993-02-01 | 1994-08-04 | Hoechst Ag | Sulfonsäureester, damit hergestellte strahlungsempfindliche Gemische und deren Verwendung |
JPH06230574A (ja) * | 1993-02-05 | 1994-08-19 | Fuji Photo Film Co Ltd | ポジ型感光性組成物 |
JPH06295064A (ja) | 1993-04-09 | 1994-10-21 | Kansai Paint Co Ltd | 感光性組成物及びパターンの製造方法 |
US5352297A (en) * | 1993-07-08 | 1994-10-04 | Peters David E | Railroad car spraying method and apparatus |
US5635333A (en) * | 1994-12-28 | 1997-06-03 | Shipley Company, L.L.C. | Antireflective coating process |
KR0154387B1 (ko) * | 1995-04-01 | 1998-11-16 | 김주용 | 음성다중 시스템을 적용한 디지탈 오디오 부호화기 |
US5731386A (en) * | 1995-05-09 | 1998-03-24 | Shipley Company, L.L.C. | Polymer for positive acid catalyzed resists |
JPH0954437A (ja) * | 1995-06-05 | 1997-02-25 | Fuji Photo Film Co Ltd | 化学増幅型ポジレジスト組成物 |
US6451394B1 (en) * | 1995-06-07 | 2002-09-17 | Owens Corning Fiberglas Technology, Inc. | Asphalt block resistant to cold flow |
TW477913B (en) * | 1995-11-02 | 2002-03-01 | Shinetsu Chemical Co | Sulfonium salts and chemically amplified positive resist compositions |
KR100536824B1 (ko) | 1996-03-07 | 2006-03-09 | 스미토모 베이클라이트 가부시키가이샤 | 산불안정성펜던트기를지닌다중고리중합체를포함하는포토레지스트조성물 |
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 |
JP3587325B2 (ja) | 1996-03-08 | 2004-11-10 | 富士写真フイルム株式会社 | ポジ型感光性組成物 |
JP3198915B2 (ja) * | 1996-04-02 | 2001-08-13 | 信越化学工業株式会社 | 化学増幅ポジ型レジスト材料 |
US5886102A (en) * | 1996-06-11 | 1999-03-23 | Shipley Company, L.L.C. | Antireflective coating compositions |
US5652297A (en) * | 1996-08-16 | 1997-07-29 | Hoechst Celanese Corporation | Aqueous antireflective coatings for photoresist compositions |
CA2243381A1 (en) * | 1996-11-20 | 1998-05-28 | Polaroid Corporation | Protective overcoat useful for enhancing an article's resistance to ambient humidity |
KR100265597B1 (ko) | 1996-12-30 | 2000-09-15 | 김영환 | Arf 감광막 수지 및 그 제조방법 |
US6808859B1 (en) | 1996-12-31 | 2004-10-26 | Hyundai Electronics Industries Co., Ltd. | ArF photoresist copolymers |
TW432257B (en) * | 1997-01-31 | 2001-05-01 | Shinetsu Chemical Co | High molecular weight silicone compound, chemically amplified positive resist composition and patterning method |
US5939236A (en) * | 1997-02-07 | 1999-08-17 | Shipley Company, L.L.C. | Antireflective coating compositions comprising photoacid generators |
US6103445A (en) * | 1997-03-07 | 2000-08-15 | Board Of Regents, The University Of Texas System | Photoresist compositions comprising norbornene derivative polymers with acid labile groups |
US5981145A (en) * | 1997-04-30 | 1999-11-09 | Clariant Finance (Bvi) Limited | Light absorbing polymers |
US6054254A (en) * | 1997-07-03 | 2000-04-25 | Kabushiki Kaisha Toshiba | Composition for underlying film and method of forming a pattern using the film |
US6124077A (en) * | 1997-09-05 | 2000-09-26 | Kansai Paint Co., Ltd. | Visible light-sensitive compositions and pattern formation process |
DE19742013A1 (de) | 1997-09-24 | 1999-03-25 | Basf Ag | Offenzellige Hartschaumstoffe auf Isocyanatbasis |
KR100566042B1 (ko) * | 1997-10-07 | 2006-05-25 | 간사이 페인트 가부시키가이샤 | 포지티브형전착포토레지스트조성물및패턴의제조방법 |
JP3676918B2 (ja) * | 1997-10-09 | 2005-07-27 | 富士通株式会社 | レジスト材料及びレジストパターンの形成方法 |
US5882996A (en) * | 1997-10-14 | 1999-03-16 | Industrial Technology Research Institute | Method of self-aligned dual damascene patterning using developer soluble arc interstitial layer |
US5935760A (en) * | 1997-10-20 | 1999-08-10 | Brewer Science Inc. | Thermosetting polyester anti-reflective coatings for multilayer photoresist processes |
KR100279497B1 (ko) | 1998-07-16 | 2001-02-01 | 박찬구 | 술포늄 염의 제조방법 |
TWI250379B (en) | 1998-08-07 | 2006-03-01 | Az Electronic Materials Japan | Chemical amplified radiation-sensitive composition which contains onium salt and generator |
US6630285B2 (en) * | 1998-10-15 | 2003-10-07 | Mitsui Chemicals, Inc. | Positive sensitive resin composition and a process for forming a resist pattern therewith |
US6114085A (en) * | 1998-11-18 | 2000-09-05 | Clariant Finance (Bvi) Limited | Antireflective composition for a deep ultraviolet photoresist |
US6251562B1 (en) * | 1998-12-23 | 2001-06-26 | International Business Machines Corporation | Antireflective polymer and method of use |
US6200728B1 (en) * | 1999-02-20 | 2001-03-13 | Shipley Company, L.L.C. | Photoresist compositions comprising blends of photoacid generators |
KR100320773B1 (ko) * | 1999-05-31 | 2002-01-17 | 윤종용 | 포토레지스트 조성물 |
US6455230B1 (en) * | 1999-06-04 | 2002-09-24 | Agfa-Gevaert | Method for preparing a lithographic printing plate by ablation of a heat sensitive ablatable imaging element |
JP4364969B2 (ja) * | 1999-07-05 | 2009-11-18 | 関西ペイント株式会社 | ポジ型感熱性樹脂組成物及びそれを用いたレジストパターン形成方法 |
US6110653A (en) * | 1999-07-26 | 2000-08-29 | International Business Machines Corporation | Acid sensitive ARC and method of use |
US6187506B1 (en) * | 1999-08-05 | 2001-02-13 | Clariant Finance (Bvi) Limited | Antireflective coating for photoresist compositions |
US6338934B1 (en) * | 1999-08-26 | 2002-01-15 | International Business Machines Corporation | Hybrid resist based on photo acid/photo base blending |
US6447980B1 (en) | 2000-07-19 | 2002-09-10 | Clariant Finance (Bvi) Limited | Photoresist composition for deep UV and process thereof |
JP3948646B2 (ja) * | 2000-08-31 | 2007-07-25 | 東京応化工業株式会社 | 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 |
TW583503B (en) * | 2000-12-01 | 2004-04-11 | Kansai Paint Co Ltd | Method of forming conductive pattern |
EP1262832A1 (en) | 2001-05-31 | 2002-12-04 | ASML Netherlands B.V. | Lithographic apparatus, device manufacturing method, and device manufactured thereby |
KR100465866B1 (ko) * | 2001-10-26 | 2005-01-13 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
US6723488B2 (en) | 2001-11-07 | 2004-04-20 | Clariant Finance (Bvi) Ltd | Photoresist composition for deep UV radiation containing an additive |
US7070914B2 (en) * | 2002-01-09 | 2006-07-04 | Az Electronic Materials Usa Corp. | Process for producing an image using a first minimum bottom antireflective coating composition |
US20030215736A1 (en) * | 2002-01-09 | 2003-11-20 | Oberlander Joseph E. | Negative-working photoimageable bottom antireflective coating |
US6844131B2 (en) * | 2002-01-09 | 2005-01-18 | Clariant Finance (Bvi) Limited | Positive-working photoimageable bottom antireflective coating |
US6846612B2 (en) * | 2002-02-01 | 2005-01-25 | Brewer Science Inc. | Organic anti-reflective coating compositions for advanced microlithography |
KR20030068729A (ko) * | 2002-02-16 | 2003-08-25 | 삼성전자주식회사 | 반사 방지용 광흡수막 형성 조성물 및 이를 이용한 반도체소자의 패턴 형성 방법 |
US7265431B2 (en) | 2002-05-17 | 2007-09-04 | Intel Corporation | Imageable bottom anti-reflective coating for high resolution lithography |
KR100636663B1 (ko) * | 2002-06-24 | 2006-10-23 | 주식회사 하이닉스반도체 | 유기 반사방지막 조성물 및 이를 이용한 포토레지스트의패턴 형성 방법 |
JP3994270B2 (ja) * | 2002-06-25 | 2007-10-17 | 日産化学工業株式会社 | 反射防止膜の形成方法 |
KR20040009384A (ko) * | 2002-07-23 | 2004-01-31 | 삼성전자주식회사 | 포토레지스트용 현상액에 용해되는 유기 바닥 반사 방지조성물과 이를 이용한 사진 식각 공정 |
CN100371826C (zh) * | 2002-08-26 | 2008-02-27 | 住友化学工业株式会社 | 磺酸盐和光刻胶组合物 |
US7358408B2 (en) | 2003-05-16 | 2008-04-15 | Az Electronic Materials Usa Corp. | Photoactive compounds |
US7223518B2 (en) | 2003-06-06 | 2007-05-29 | Georgia Tech Research Corporation | Compositions and methods of use thereof |
JP2005040154A (ja) * | 2003-07-22 | 2005-02-17 | Sansha Electric Mfg Co Ltd | 注射針安全化処理装置 |
US7186486B2 (en) * | 2003-08-04 | 2007-03-06 | Micronic Laser Systems Ab | Method to pattern a substrate |
JP4173414B2 (ja) * | 2003-08-28 | 2008-10-29 | 東京応化工業株式会社 | 反射防止膜形成用組成物およびレジストパターンの形成方法 |
TWI366067B (en) * | 2003-09-10 | 2012-06-11 | Fujifilm Corp | Photosensitive composition and pattern forming method using the same |
JP4474246B2 (ja) * | 2003-09-19 | 2010-06-02 | 富士フイルム株式会社 | 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 |
DE102004014292A1 (de) | 2004-03-22 | 2005-10-20 | Lurgi Ag | Koproduktion von Methanol und Ammoniak aus Erdgas |
US20050214674A1 (en) | 2004-03-25 | 2005-09-29 | Yu Sui | Positive-working photoimageable bottom antireflective coating |
US20050255410A1 (en) * | 2004-04-29 | 2005-11-17 | Guerrero Douglas J | Anti-reflective coatings using vinyl ether crosslinkers |
EP2866093A1 (en) | 2004-05-14 | 2015-04-29 | Nissan Chemical Industries, Limited | Anti-reflective coating forming composition containing vinyl ether compound and polyimide |
US20050271974A1 (en) | 2004-06-08 | 2005-12-08 | Rahman M D | Photoactive compounds |
JP4491283B2 (ja) | 2004-06-10 | 2010-06-30 | 信越化学工業株式会社 | 反射防止膜形成用組成物を用いたパターン形成方法 |
US7119031B2 (en) | 2004-06-28 | 2006-10-10 | Micron Technology, Inc. | Methods of forming patterned photoresist layers over semiconductor substrates |
US7816071B2 (en) | 2005-02-10 | 2010-10-19 | Az Electronic Materials Usa Corp. | Process of imaging a photoresist with multiple antireflective coatings |
US7521170B2 (en) | 2005-07-12 | 2009-04-21 | Az Electronic Materials Usa Corp. | Photoactive compounds |
US8383322B2 (en) * | 2005-08-05 | 2013-02-26 | Taiwan Semiconductor Manufacturing Company, Ltd. | Immersion lithography watermark reduction |
US7678528B2 (en) | 2005-11-16 | 2010-03-16 | Az Electronic Materials Usa Corp. | Photoactive compounds |
KR100703007B1 (ko) | 2005-11-17 | 2007-04-06 | 삼성전자주식회사 | 감광성 유기 반사 방지막 형성용 조성물 및 이를 이용한패턴 형성 방법 |
JP5100115B2 (ja) * | 2006-03-16 | 2012-12-19 | 東洋合成工業株式会社 | スルホニウム塩及び酸発生剤 |
JP4548616B2 (ja) | 2006-05-15 | 2010-09-22 | 信越化学工業株式会社 | 熱酸発生剤及びこれを含むレジスト下層膜材料、並びにこのレジスト下層膜材料を用いたパターン形成方法 |
US7816069B2 (en) | 2006-06-23 | 2010-10-19 | International Business Machines Corporation | Graded spin-on organic antireflective coating for photolithography |
US8088548B2 (en) | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
US8455176B2 (en) * | 2008-11-12 | 2013-06-04 | Az Electronic Materials Usa Corp. | Coating composition |
US8632948B2 (en) * | 2009-09-30 | 2014-01-21 | Az Electronic Materials Usa Corp. | Positive-working photoimageable bottom antireflective coating |
US20110086312A1 (en) * | 2009-10-09 | 2011-04-14 | Dammel Ralph R | Positive-Working Photoimageable Bottom Antireflective Coating |
-
2004
- 2004-03-25 US US10/808,884 patent/US20050214674A1/en not_active Abandoned
-
2005
- 2005-03-07 TW TW094106806A patent/TWI407259B/zh active
- 2005-03-07 TW TW100147535A patent/TWI407257B/zh active
- 2005-03-23 JP JP2007504508A patent/JP5008079B2/ja active Active
- 2005-03-23 CN CN2005800118695A patent/CN1942826B/zh active Active
- 2005-03-23 KR KR1020117027434A patent/KR20120000111A/ko not_active Application Discontinuation
- 2005-03-23 KR KR1020067022194A patent/KR101241468B1/ko active IP Right Grant
- 2005-03-23 CN CN201210393108.2A patent/CN102879999B/zh active Active
- 2005-03-23 WO PCT/IB2005/000773 patent/WO2005093513A2/en active Application Filing
- 2005-03-23 SG SG2012049037A patent/SG183654A1/en unknown
- 2005-03-23 SG SG2012049045A patent/SG183655A1/en unknown
- 2005-03-23 MY MYPI20051260A patent/MY147755A/en unknown
- 2005-03-23 EP EP05718269.3A patent/EP1738225B1/en active Active
-
2007
- 2007-10-22 US US11/876,332 patent/US7824837B2/en not_active Expired - Lifetime
- 2007-10-24 US US11/877,891 patent/US8039202B2/en not_active Expired - Lifetime
-
2011
- 2011-03-17 JP JP2011059412A patent/JP5019338B2/ja active Active
-
2012
- 2012-01-12 JP JP2012003737A patent/JP5391462B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
US20080038666A1 (en) | 2008-02-14 |
KR101241468B1 (ko) | 2013-03-08 |
JP5391462B2 (ja) | 2014-01-15 |
TWI407257B (zh) | 2013-09-01 |
EP1738225A2 (en) | 2007-01-03 |
US20050214674A1 (en) | 2005-09-29 |
TW200600974A (en) | 2006-01-01 |
CN102879999B (zh) | 2014-12-24 |
MY147755A (en) | 2013-01-15 |
EP1738225B1 (en) | 2018-11-14 |
KR20070043698A (ko) | 2007-04-25 |
JP5019338B2 (ja) | 2012-09-05 |
WO2005093513A3 (en) | 2006-02-23 |
CN1942826A (zh) | 2007-04-04 |
CN1942826B (zh) | 2012-11-28 |
WO2005093513A2 (en) | 2005-10-06 |
TW201214049A (en) | 2012-04-01 |
US7824837B2 (en) | 2010-11-02 |
US20080090184A1 (en) | 2008-04-17 |
SG183654A1 (en) | 2012-09-27 |
KR20120000111A (ko) | 2012-01-03 |
JP2011150365A (ja) | 2011-08-04 |
JP2012103723A (ja) | 2012-05-31 |
JP2008501985A (ja) | 2008-01-24 |
TWI407259B (zh) | 2013-09-01 |
CN102879999A (zh) | 2013-01-16 |
US8039202B2 (en) | 2011-10-18 |
SG183655A1 (en) | 2012-09-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5008079B2 (ja) | 光結像性ポジ型底面反射防止膜 | |
EP1465877B1 (en) | Positive-working photoimageable bottom antireflective coating | |
TWI558778B (zh) | 底部抗反射塗料組合物及其方法 | |
JP5604734B2 (ja) | ポジ型光像形成性底面反射防止コーティング | |
EP2486453B1 (en) | Positive-working photoimageable bottom antireflective coating | |
US20060063105A1 (en) | Negative-working photoimageable bottom antireflective coating |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080220 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080220 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20100518 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20101012 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101224 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110106 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110317 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20110317 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110913 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20111212 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20111219 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20120111 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120112 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120424 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20120509 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20120509 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120524 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5008079 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150608 Year of fee payment: 3 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |