KR20070030200A - 광활성 화합물 - Google Patents
광활성 화합물 Download PDFInfo
- Publication number
- KR20070030200A KR20070030200A KR1020067024474A KR20067024474A KR20070030200A KR 20070030200 A KR20070030200 A KR 20070030200A KR 1020067024474 A KR1020067024474 A KR 1020067024474A KR 20067024474 A KR20067024474 A KR 20067024474A KR 20070030200 A KR20070030200 A KR 20070030200A
- Authority
- KR
- South Korea
- Prior art keywords
- methacrylate
- adamantyl
- poly
- hydroxy
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 25
- -1 R 31 Chemical compound 0.000 claims description 109
- 229920002120 photoresistant polymer Polymers 0.000 claims description 103
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 58
- 229920000642 polymer Polymers 0.000 claims description 53
- 239000000758 substrate Substances 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000002950 monocyclic group Chemical group 0.000 claims description 38
- 238000000576 coating method Methods 0.000 claims description 37
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 37
- 239000011248 coating agent Substances 0.000 claims description 35
- 125000003367 polycyclic group Polymers 0.000 claims description 35
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- LJZJMIZQMNDARW-UHFFFAOYSA-N decan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCCCC(CC)OC(=O)C(C)=C LJZJMIZQMNDARW-UHFFFAOYSA-N 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 9
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000004065 semiconductor Substances 0.000 claims description 7
- CIKZJZIPTDPBCW-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-4-carboxylate Chemical compound C1CC2C=CC1(C(=O)OC(C)(C)C)C2 CIKZJZIPTDPBCW-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 238000010304 firing Methods 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- 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 claims description 5
- HLWRYLIHOIJMSF-UHFFFAOYSA-N 1-tert-butylbicyclo[2.2.1]hept-2-ene Chemical compound C(C)(C)(C)C12CCC(C=C1)C2 HLWRYLIHOIJMSF-UHFFFAOYSA-N 0.000 claims description 5
- OQIKQWQXNXHQCU-UHFFFAOYSA-N bicyclo[2.2.1]heptane;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1CC2CCC1C2 OQIKQWQXNXHQCU-UHFFFAOYSA-N 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- YRPLSAWATHBYFB-UHFFFAOYSA-N (2-methyl-2-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)C=C)C2C3 YRPLSAWATHBYFB-UHFFFAOYSA-N 0.000 claims description 4
- IFDUTQGPGFEDHJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;oxolan-2-one Chemical compound CC(=C)C(O)=O.O=C1CCCO1 IFDUTQGPGFEDHJ-UHFFFAOYSA-N 0.000 claims description 4
- AKGGHYOWZFPMTM-UHFFFAOYSA-N 4-bicyclo[2.2.1]heptanyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1CC2CCC1(OC(=O)C(=C)C)C2 AKGGHYOWZFPMTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 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 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 229910003849 O-Si Inorganic materials 0.000 claims description 3
- 229910003872 O—Si Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000005460 perfluorocycloalkyl group Chemical group 0.000 claims description 3
- DGPNNZGZXFUKKC-UHFFFAOYSA-N 2-cyclopentylpent-2-enoic acid Chemical compound CCC=C(C(O)=O)C1CCCC1 DGPNNZGZXFUKKC-UHFFFAOYSA-N 0.000 claims description 2
- MZVABYGYVXBZDP-UHFFFAOYSA-N 1-adamantyl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C(=C)C)C3 MZVABYGYVXBZDP-UHFFFAOYSA-N 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 claims 1
- 238000004377 microelectronic Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 150000001925 cycloalkenes Chemical class 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 230000005855 radiation Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RMGYNVXHFIZVCG-UHFFFAOYSA-N (4-hydroxy-3,5-dimethylphenyl)-dimethylsulfanium;chloride Chemical compound [Cl-].C[S+](C)C1=CC(C)=C(O)C(C)=C1 RMGYNVXHFIZVCG-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BHLMMLLQMGOTRS-UHFFFAOYSA-N FC(C(C(C(S(=O)(=O)OOC(C(F)(F)F)F)(F)F)(F)F)(F)F)F.[Li] Chemical compound FC(C(C(C(S(=O)(=O)OOC(C(F)(F)F)F)(F)F)(F)F)(F)F)F.[Li] BHLMMLLQMGOTRS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000001393 microlithography Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000126 substance Substances 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
- 238000012546 transfer Methods 0.000 description 3
- FDOANYJWOYTZAP-UHFFFAOYSA-N (1-ethylcyclopentyl) prop-2-enoate Chemical compound C=CC(=O)OC1(CC)CCCC1 FDOANYJWOYTZAP-UHFFFAOYSA-N 0.000 description 2
- UPBXIPQYLTVOTD-UHFFFAOYSA-O (4-hydroxy-3,5-dimethylphenyl)-dimethylsulfanium;1,2,2,2-tetrafluoroethoxy 1,1,2,2,3,3,4,4-octafluorobutane-1-sulfonate Chemical compound C[S+](C)C1=CC(C)=C(O)C(C)=C1.FC(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)OOC(F)C(F)(F)F UPBXIPQYLTVOTD-UHFFFAOYSA-O 0.000 description 2
- CEZCTKYAEUCICK-UHFFFAOYSA-N 2-ethylundec-7-enoic acid Chemical compound CCCC=CCCCCC(CC)C(O)=O CEZCTKYAEUCICK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000006117 anti-reflective coating Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 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
- 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
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000004090 dissolution Methods 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
- 150000002148 esters Chemical class 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 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
- HQHYZFPWPZCSIZ-UHFFFAOYSA-N (4-acetyloxy-3,5-dimethylphenyl)-dimethylsulfanium;2,2,2-trifluoroethoxy 1,1,2,2,3,3,4,4-octafluorobutane-1-sulfonate Chemical compound C[S+](C)C1=CC(C)=C(OC(C)=O)C(C)=C1.FC(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)OOCC(F)(F)F HQHYZFPWPZCSIZ-UHFFFAOYSA-N 0.000 description 1
- XRHBQGFVJGGAPZ-UHFFFAOYSA-O (4-hydroxy-3,5-dimethylphenyl)-dimethylsulfanium;2,2,2-trifluoroethoxy 1,1,2,2,3,3,4,4-octafluorobutane-1-sulfonate Chemical compound C[S+](C)C1=CC(C)=C(O)C(C)=C1.FC(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)OOCC(F)(F)F XRHBQGFVJGGAPZ-UHFFFAOYSA-O 0.000 description 1
- BCOJEFUMFRSSRC-UHFFFAOYSA-N (4-methoxyphenyl)-dimethylsulfanium;1,2,2,2-tetrafluoroethoxy 1,1,2,2,3,3,4,4-octafluorobutane-1-sulfonate Chemical compound COC1=CC=C([S+](C)C)C=C1.FC(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)OOC(F)C(F)(F)F BCOJEFUMFRSSRC-UHFFFAOYSA-N 0.000 description 1
- DZHKMTPEXHRSIZ-UHFFFAOYSA-M (4-methoxyphenyl)-dimethylsulfanium;chloride Chemical compound [Cl-].COC1=CC=C([S+](C)C)C=C1 DZHKMTPEXHRSIZ-UHFFFAOYSA-M 0.000 description 1
- ZROFAXCQYPKWCY-UHFFFAOYSA-N (5-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1COC(=O)C1 ZROFAXCQYPKWCY-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- ZCGZOPIPEZCKKQ-UHFFFAOYSA-N 2-ethoxy-2-methylpropanoic acid Chemical compound CCOC(C)(C)C(O)=O ZCGZOPIPEZCKKQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100215341 Arabidopsis thaliana ACT12 gene Proteins 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 101100435268 Caenorhabditis elegans arf-1.2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010011703 Cyanosis Diseases 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- MVDBOXMPYDDDNE-UHFFFAOYSA-N FC(C(C(C(S(=O)(=O)OOCC(F)(F)F)(F)F)(F)F)(F)F)F.[Li] Chemical compound FC(C(C(C(S(=O)(=O)OOCC(F)(F)F)(F)F)(F)F)(F)F)F.[Li] MVDBOXMPYDDDNE-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 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
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000007687 exposure technique Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002848 norbornenes Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical class C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 125000005023 xylyl group Chemical group 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/492—Photosoluble emulsions
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Materials For Photolithography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/863,042 | 2004-06-08 | ||
| US10/863,042 US20050271974A1 (en) | 2004-06-08 | 2004-06-08 | Photoactive compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20070030200A true KR20070030200A (ko) | 2007-03-15 |
Family
ID=35044987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067024474A Withdrawn KR20070030200A (ko) | 2004-06-08 | 2005-06-08 | 광활성 화합물 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050271974A1 (https=) |
| EP (1) | EP1766474A2 (https=) |
| JP (1) | JP2008501779A (https=) |
| KR (1) | KR20070030200A (https=) |
| CN (1) | CN1961260A (https=) |
| TW (1) | TW200613256A (https=) |
| WO (1) | WO2005121894A2 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050214674A1 (en) | 2004-03-25 | 2005-09-29 | Yu Sui | Positive-working photoimageable bottom antireflective coating |
| US7255970B2 (en) * | 2005-07-12 | 2007-08-14 | Az Electronic Materials Usa Corp. | Photoresist composition for imaging thick films |
| JP4695941B2 (ja) * | 2005-08-19 | 2011-06-08 | 富士フイルム株式会社 | 液浸露光用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 |
| US20070105040A1 (en) * | 2005-11-10 | 2007-05-10 | Toukhy Medhat A | Developable undercoating composition for thick photoresist layers |
| US7601482B2 (en) * | 2006-03-28 | 2009-10-13 | Az Electronic Materials Usa Corp. | Negative photoresist compositions |
| JP4881692B2 (ja) * | 2006-10-23 | 2012-02-22 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物に用いられる化合物及び該感光性組成物を用いたパターン形成方法 |
| US20080171270A1 (en) * | 2007-01-16 | 2008-07-17 | Munirathna Padmanaban | Polymers Useful in Photoresist Compositions and Compositions Thereof |
| JP5364256B2 (ja) * | 2007-06-13 | 2013-12-11 | 東京応化工業株式会社 | 化合物、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
| US8227624B2 (en) * | 2007-08-07 | 2012-07-24 | Adeka Corporation | Aromatic sulfonium salt compound |
| US8252503B2 (en) * | 2007-08-24 | 2012-08-28 | Az Electronic Materials Usa Corp. | Photoresist compositions |
| 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 |
| US8906594B2 (en) | 2012-06-15 | 2014-12-09 | Az Electronic Materials (Luxembourg) S.A.R.L. | Negative-working thick film photoresist |
| US9012126B2 (en) | 2012-06-15 | 2015-04-21 | Az Electronic Materials (Luxembourg) S.A.R.L. | Positive photosensitive material |
| TWI498675B (zh) * | 2012-09-15 | 2015-09-01 | 羅門哈斯電子材料有限公司 | 酸產生劑化合物及含該化合物之光阻劑 |
| KR20160003628A (ko) | 2013-04-23 | 2016-01-11 | 미츠비시 가스 가가쿠 가부시키가이샤 | 신규 지환식 에스테르 화합물, (메트)아크릴 공중합체 및 그것을 포함하는 감광성 수지 조성물 |
| JP6442271B2 (ja) * | 2014-12-22 | 2018-12-19 | デクセリアルズ株式会社 | 化合物、熱硬化性樹脂組成物、及び熱硬化性シート |
| TWI731961B (zh) | 2016-04-19 | 2021-07-01 | 德商馬克專利公司 | 正向感光材料及形成正向凸紋影像之方法 |
| JP6782569B2 (ja) * | 2016-06-28 | 2020-11-11 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
| KR102261808B1 (ko) | 2016-08-09 | 2021-06-07 | 리지필드 액퀴지션 | 환경적으로 안정한 후막성 화학증폭형 레지스트 |
| EP3847506A1 (en) | 2018-09-05 | 2021-07-14 | Merck Patent GmbH | Positive working photosensitive material |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021197A (en) * | 1988-06-16 | 1991-06-04 | Mitsubishi Gas Chemical Company, Inc. | Process for production of sulfonium compounds |
| DE3902114A1 (de) * | 1989-01-25 | 1990-08-02 | Basf Ag | Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare sulfoniumsalze und verfahren zu deren herstellung |
| US5075476A (en) * | 1989-06-07 | 1991-12-24 | Mitsubishi Gas Chemical Company, Inc. | Process for production of sulfonium compounds and novel methylthiphenol derivatives |
| US5252436A (en) * | 1989-12-15 | 1993-10-12 | Basf Aktiengesellschaft | Process for developing a positive-working photoresist containing poly(p-hydroxystyrene) and sulfonium salt with an aqueous developer containing basic organic compounds |
| US5274148A (en) * | 1992-08-10 | 1993-12-28 | Isp Investments, Inc. | Dialky alkoxy phenyl sulfonium salt cationic initiators |
| WO1995024387A1 (en) * | 1994-03-09 | 1995-09-14 | Nippon Soda Co., Ltd. | Sulfonium salt compound and polymerization initiator |
| JP2770740B2 (ja) * | 1994-07-14 | 1998-07-02 | 日本電気株式会社 | 橋かけ環式アルキル基を有するスルホニウム塩化合物および光酸発生剤 |
| EP0846681B1 (en) * | 1995-08-22 | 2003-12-03 | Nippon Soda Co., Ltd. | Novel sulfonium salt compounds, polymerization initiator, curable composition, and curing method |
| 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 |
| US5693903A (en) * | 1996-04-04 | 1997-12-02 | Coda Music Technology, Inc. | Apparatus and method for analyzing vocal audio data to provide accompaniment to a vocalist |
| EP1179750B1 (en) * | 2000-08-08 | 2012-07-25 | FUJIFILM Corporation | Positive photosensitive composition and method for producing a precision integrated circuit element using the same |
| JP4226803B2 (ja) * | 2000-08-08 | 2009-02-18 | 富士フイルム株式会社 | ポジ型感光性組成物 |
| JP4150509B2 (ja) * | 2000-11-20 | 2008-09-17 | 富士フイルム株式会社 | ポジ型感光性組成物 |
| US6749987B2 (en) * | 2000-10-20 | 2004-06-15 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
| US6855476B2 (en) * | 2001-04-05 | 2005-02-15 | Arch Specialty Chemicals, Inc. | Photoacid generators for use in photoresist compositions |
| JP4054978B2 (ja) * | 2001-08-24 | 2008-03-05 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| US7105267B2 (en) * | 2001-08-24 | 2006-09-12 | Shin-Etsu Chemical Co., Ltd. | Resist compositions and patterning process |
| JP2003228167A (ja) * | 2002-02-01 | 2003-08-15 | Fuji Photo Film Co Ltd | ネガ型レジスト組成物 |
| JP3841399B2 (ja) * | 2002-02-21 | 2006-11-01 | 富士写真フイルム株式会社 | ポジ型レジスト組成物 |
| TWI284779B (en) * | 2002-06-07 | 2007-08-01 | Fujifilm Corp | Photosensitive resin composition |
| US20030235775A1 (en) * | 2002-06-13 | 2003-12-25 | Munirathna Padmanaban | Photoresist composition for deep ultraviolet lithography comprising a mixture of photoactive compounds |
| US6841333B2 (en) * | 2002-11-01 | 2005-01-11 | 3M Innovative Properties Company | Ionic photoacid generators with segmented hydrocarbon-fluorocarbon sulfonate anions |
| US7358408B2 (en) * | 2003-05-16 | 2008-04-15 | Az Electronic Materials Usa Corp. | Photoactive compounds |
-
2004
- 2004-06-08 US US10/863,042 patent/US20050271974A1/en not_active Abandoned
-
2005
- 2005-05-26 TW TW094117283A patent/TW200613256A/zh unknown
- 2005-06-08 KR KR1020067024474A patent/KR20070030200A/ko not_active Withdrawn
- 2005-06-08 EP EP05756699A patent/EP1766474A2/en not_active Withdrawn
- 2005-06-08 CN CNA2005800173866A patent/CN1961260A/zh active Pending
- 2005-06-08 WO PCT/IB2005/001923 patent/WO2005121894A2/en not_active Ceased
- 2005-06-08 JP JP2007526597A patent/JP2008501779A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005121894A3 (en) | 2006-03-30 |
| JP2008501779A (ja) | 2008-01-24 |
| CN1961260A (zh) | 2007-05-09 |
| US20050271974A1 (en) | 2005-12-08 |
| WO2005121894A2 (en) | 2005-12-22 |
| TW200613256A (en) | 2006-05-01 |
| EP1766474A2 (en) | 2007-03-28 |
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