JP2007520587A - 低多分散性の光画像形成可能なアクリルポリマー、フォトレジストおよびマイクロリソグラフィーのための方法 - Google Patents
低多分散性の光画像形成可能なアクリルポリマー、フォトレジストおよびマイクロリソグラフィーのための方法 Download PDFInfo
- Publication number
- JP2007520587A JP2007520587A JP2006528161A JP2006528161A JP2007520587A JP 2007520587 A JP2007520587 A JP 2007520587A JP 2006528161 A JP2006528161 A JP 2006528161A JP 2006528161 A JP2006528161 A JP 2006528161A JP 2007520587 A JP2007520587 A JP 2007520587A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- acrylate
- meth
- substituted
- 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.)
- Pending
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 37
- 229920000058 polyacrylate Polymers 0.000 title claims abstract description 11
- 238000001393 microlithography Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 73
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 39
- 238000012546 transfer Methods 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims description 69
- -1 2-hydroxy-1,1,2-trimethylpropyl ester Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 34
- 239000012986 chain transfer agent Substances 0.000 claims description 33
- 150000003254 radicals Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 18
- 125000000524 functional group Chemical group 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 16
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000012989 trithiocarbonate Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 8
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical group [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004663 dialkyl amino 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
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229920001002 functional polymer Polymers 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract description 7
- 230000002441 reversible effect Effects 0.000 abstract description 4
- 238000013467 fragmentation Methods 0.000 abstract description 3
- 238000006062 fragmentation reaction Methods 0.000 abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- 239000003999 initiator Substances 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000011161 development Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 241001446467 Mama Species 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000000977 initiatory effect Effects 0.000 description 11
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 239000012530 fluid Substances 0.000 description 9
- DKDKCSYKDZNMMA-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1(O)CC2(OC(=O)C=C)C3 DKDKCSYKDZNMMA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 6
- KPMKEVXVVHNIEY-RITPCOANSA-N norcamphor Chemical compound C1C[C@@H]2C(=O)C[C@H]1C2 KPMKEVXVVHNIEY-RITPCOANSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- AISZNMCRXZWVAT-UHFFFAOYSA-N 2-ethylsulfanylcarbothioylsulfanyl-2-methylpropanenitrile Chemical compound CCSC(=S)SC(C)(C)C#N AISZNMCRXZWVAT-UHFFFAOYSA-N 0.000 description 5
- 239000012987 RAFT agent Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000003158 alcohol group Chemical group 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000001565 modulated differential scanning calorimetry Methods 0.000 description 4
- 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- NYZSKEULTVZUAW-UHFFFAOYSA-N 2,2-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1(C(F)(F)F)CO1 NYZSKEULTVZUAW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000012988 Dithioester Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000023 Kugelrohr distillation Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000005022 dithioester group Chemical group 0.000 description 3
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 0 *ON(C(c1ccccc11)=O)C1=[U] Chemical compound *ON(C(c1ccccc11)=O)C1=[U] 0.000 description 2
- RNTXYZIABJIFKQ-UHFFFAOYSA-N 4-cyano-4-dodecylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCCCCCCCCCCCSC(=S)SC(C)(C#N)CCC(O)=O RNTXYZIABJIFKQ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000010968 computed tomography angiography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- KPMKEVXVVHNIEY-UHFFFAOYSA-N norcamphor Chemical compound C1CC2C(=O)CC1C2 KPMKEVXVVHNIEY-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000000643 oven drying Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 235000019394 potassium persulphate Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940080818 propionamide Drugs 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
- 238000010926 purge Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000012991 xanthate Substances 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- DCTVCFJTKSQXED-UHFFFAOYSA-N (2-ethyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(CC)(OC(=O)C(C)=C)C2C3 DCTVCFJTKSQXED-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- DAVVKEZTUOGEAK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOC(=O)C(C)=C DAVVKEZTUOGEAK-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- LDQYWNUWKVADJV-UHFFFAOYSA-N 2-[(1-amino-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanamide;dihydrate Chemical compound O.O.NC(=O)C(C)(C)N=NC(C)(C)C(N)=O LDQYWNUWKVADJV-UHFFFAOYSA-N 0.000 description 1
- IWTIJBANDVIHPX-UHFFFAOYSA-N 2-[(2-cyano-5-hydroxypentan-2-yl)diazenyl]-5-hydroxy-2-methylpentanenitrile Chemical compound OCCCC(C)(C#N)N=NC(C)(CCCO)C#N IWTIJBANDVIHPX-UHFFFAOYSA-N 0.000 description 1
- LINFYYCWDHJMLA-UHFFFAOYSA-N 2-cyanobutan-2-yl pyrrole-1-carbodithioate Chemical compound CCC(C)(C#N)SC(=S)N1C=CC=C1 LINFYYCWDHJMLA-UHFFFAOYSA-N 0.000 description 1
- KOQQFZSGVDYJLH-UHFFFAOYSA-N 2-cyanopropan-2-yl pyrrole-1-carbodithioate Chemical compound N#CC(C)(C)SC(=S)N1C=CC=C1 KOQQFZSGVDYJLH-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GAMLHIPFVLVGSE-UHFFFAOYSA-N C(#N)CS(C(S)=S)CCCCCCCCCCCC Chemical compound C(#N)CS(C(S)=S)CCCCCCCCCCCC GAMLHIPFVLVGSE-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229920000028 Gradient copolymer Polymers 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MARDFMMXBWIRTK-UHFFFAOYSA-N [F].[Ar] Chemical compound [F].[Ar] MARDFMMXBWIRTK-UHFFFAOYSA-N 0.000 description 1
- VFQHLZMKZVVGFQ-UHFFFAOYSA-N [F].[Kr] Chemical compound [F].[Kr] VFQHLZMKZVVGFQ-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- FJBQIWIQQRXHPK-UHFFFAOYSA-N benzyl imidazole-1-carbodithioate Chemical compound C1=CN=CN1C(=S)SCC1=CC=CC=C1 FJBQIWIQQRXHPK-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- SCUZIHSJSPFAIB-UHFFFAOYSA-L dipotassium;dioxido(sulfanylidene)-$l^{4}-sulfane Chemical compound [K+].[K+].[O-]S([S-])=O SCUZIHSJSPFAIB-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GKCPCPKXFGQXGS-UHFFFAOYSA-N ditert-butyldiazene Chemical compound CC(C)(C)N=NC(C)(C)C GKCPCPKXFGQXGS-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- YFYSUAZHCKSLCV-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxobutan-2-yl)diazenyl]-2-methylbutanoate Chemical compound COC(=O)C(C)(CC)N=NC(C)(CC)C(=O)OC YFYSUAZHCKSLCV-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- VXRNYQMFDGOGSI-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-2-[[1-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(C)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(C)(CO)CO VXRNYQMFDGOGSI-UHFFFAOYSA-N 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- AOAFIKNGZOOCRX-UHFFFAOYSA-N o-ethyl 1-phenylethylsulfanylmethanethioate Chemical compound CCOC(=S)SC(C)C1=CC=CC=C1 AOAFIKNGZOOCRX-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical class Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- KHJNXCATZZIGAX-UHFFFAOYSA-N tert-butyl 2-ethyl-2-methylheptaneperoxoate Chemical compound CCCCCC(C)(CC)C(=O)OOC(C)(C)C KHJNXCATZZIGAX-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/28—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms
- C07C35/29—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms being a (2.2.1) system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50503803P | 2003-09-22 | 2003-09-22 | |
| PCT/US2004/031242 WO2005031461A1 (en) | 2003-09-22 | 2004-09-22 | Low-polydispersity photoimageable acrylic polymers, photoresists and processes for microlithography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007520587A true JP2007520587A (ja) | 2007-07-26 |
| JP2007520587A5 JP2007520587A5 (enExample) | 2007-09-27 |
Family
ID=34392966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006528161A Pending JP2007520587A (ja) | 2003-09-22 | 2004-09-22 | 低多分散性の光画像形成可能なアクリルポリマー、フォトレジストおよびマイクロリソグラフィーのための方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7696292B2 (enExample) |
| EP (2) | EP2287671B1 (enExample) |
| JP (1) | JP2007520587A (enExample) |
| KR (1) | KR101238580B1 (enExample) |
| CN (1) | CN1853139A (enExample) |
| DE (1) | DE602004032151D1 (enExample) |
| TW (1) | TW200525292A (enExample) |
| WO (1) | WO2005031461A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007091882A (ja) * | 2005-09-29 | 2007-04-12 | Jsr Corp | 樹脂の合成法 |
| JP2015135492A (ja) * | 2013-12-31 | 2015-07-27 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | フォトレジストオーバーコート組成物 |
| JP2016026313A (ja) * | 2011-02-04 | 2016-02-12 | 日立化成株式会社 | 樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
| WO2019181228A1 (ja) * | 2018-03-19 | 2019-09-26 | 株式会社ダイセル | フォトレジスト用樹脂、フォトレジスト用樹脂の製造方法、フォトレジスト用樹脂組成物、及びパターン形成方法 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7713294B2 (en) * | 2002-08-28 | 2010-05-11 | Nomir Medical Technologies, Inc. | Near infrared microbial elimination laser systems (NIMEL) |
| JP4705426B2 (ja) * | 2005-07-14 | 2011-06-22 | 互応化学工業株式会社 | プリント配線板製造用アルカリ現像型感光性レジストインキ組成物、その硬化物およびプリント配線板 |
| JP4960614B2 (ja) * | 2005-08-12 | 2012-06-27 | セントラル硝子株式会社 | α−置換アクリル酸ノルボルナニル類及びその製造方法、並びにそれを用いた共重合体 |
| JP4650630B2 (ja) * | 2005-10-07 | 2011-03-16 | Jsr株式会社 | スペーサー用感放射線性樹脂組成物、スペーサー、およびその形成方法 |
| WO2008021291A2 (en) * | 2006-08-14 | 2008-02-21 | E. I. Du Pont De Nemours And Company | Fluorinated polymers for use in immersion lithography |
| KR101400824B1 (ko) | 2006-09-25 | 2014-05-29 | 후지필름 가부시키가이샤 | 레지스트 조성물, 이 레지스트 조성물에 사용되는 수지, 이수지의 합성에 사용되는 화합물, 및 상기 레지스트조성물을 사용한 패턴형성방법 |
| KR101446819B1 (ko) * | 2006-12-22 | 2014-10-01 | 마루젠 세끼유가가꾸 가부시키가이샤 | 반도체 리소그래피용 중합체의 제조 방법 |
| US20080248418A1 (en) * | 2007-04-04 | 2008-10-09 | William Brown Farnham | Synthesis of fluoroalcohol-substituted (meth)acrylate esters and polymers derived therefrom |
| JP6031420B2 (ja) | 2012-08-31 | 2016-11-24 | ダウ グローバル テクノロジーズ エルエルシー | 光酸発生剤を含む末端基を含むポリマー、前記ポリマーを含むフォトレジストおよびデバイスの製造方法 |
| JP5937549B2 (ja) * | 2012-08-31 | 2016-06-22 | ダウ グローバル テクノロジーズ エルエルシー | 光酸発生剤化合物、光酸発生剤化合物を含有する末端基を含むポリマー、および製造方法 |
| EP2970538B1 (en) | 2013-03-15 | 2021-10-20 | DuPont Electronics, Inc. | Polymerization process protection means |
| JP7310471B2 (ja) * | 2019-09-12 | 2023-07-19 | Jsr株式会社 | パターン形成方法及び組成物 |
| CN113861332B (zh) * | 2021-09-30 | 2023-02-24 | 宁波南大光电材料有限公司 | 一种光刻胶树脂及其聚合方法 |
| KR102723279B1 (ko) | 2021-10-19 | 2024-10-28 | 인하대학교 산학협력단 | 연속 흐름 반응 공정을 이용한 자외선 리소그래피용 포토레지스트 고분자 및 이의 제조방법 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641245A (ja) * | 1992-07-24 | 1994-02-15 | Shin Etsu Chem Co Ltd | 単分散性共重合体及びその製造方法 |
| JP2000515181A (ja) * | 1996-07-10 | 2000-11-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | リビング特性を持つ重合 |
| JP2001154362A (ja) * | 1999-11-29 | 2001-06-08 | Central Glass Co Ltd | ポジ型レジスト組成物およびパターン形成方法 |
| JP2002508409A (ja) * | 1997-12-18 | 2002-03-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | リビング性を有する重合方法およびその方法で製造されるポリマー |
| JP2003040840A (ja) * | 2001-07-24 | 2003-02-13 | Central Glass Co Ltd | 含フッ素重合性単量体およびそれを用いた高分子化合物 |
| JP2004038141A (ja) * | 2002-03-01 | 2004-02-05 | Shipley Co Llc | フォトレジスト組成物 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0196204A (ja) * | 1987-10-08 | 1989-04-14 | Hitachi Chem Co Ltd | セメント用樹脂組成物 |
| 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 |
| US6200725B1 (en) * | 1995-06-28 | 2001-03-13 | Fujitsu Limited | Chemically amplified resist compositions and process for the formation of resist patterns |
| CA2213050A1 (en) | 1996-08-21 | 1998-02-21 | John S. Manka | Compositions containing thiocarbonates and acylated-nitrogen containing compounds |
| IL139666A0 (en) * | 1997-07-21 | 2002-02-10 | Commw Scient Ind Res Org | Synthesis of dithioester chain transfer agents and use of bis (thioacyl) disulfides or dithioesters as chain transfer agents |
| JP4131062B2 (ja) * | 1998-09-25 | 2008-08-13 | 信越化学工業株式会社 | 新規なラクトン含有化合物、高分子化合物、レジスト材料及びパターン形成方法 |
| HK1048309A1 (zh) | 1999-05-04 | 2003-03-28 | 纳幕尔杜邦公司 | 多氟化环氧化物和有关聚合物以及制备方法 |
| US6790587B1 (en) * | 1999-05-04 | 2004-09-14 | E. I. Du Pont De Nemours And Company | Fluorinated polymers, photoresists and processes for microlithography |
| FR2809829B1 (fr) | 2000-06-05 | 2002-07-26 | Rhodia Chimie Sa | Nouvelle composition photosensible pour la fabrication de photoresist |
| US6441115B1 (en) * | 2000-06-30 | 2002-08-27 | Everlight Usa, Inc. | Photosensitive polymer |
| WO2003075094A1 (en) | 2002-03-01 | 2003-09-12 | E.I. Du Pont De Nemours And Company | Fluorinated copolymers for microlithography |
| TWI314247B (en) | 2002-03-04 | 2009-09-01 | Shipley Co Llc | Megative photordsists for short wavelength imaging |
| US7834113B2 (en) * | 2003-05-08 | 2010-11-16 | E. I. Du Pont De Nemours And Company | Photoresist compositions and processes for preparing the same |
| JP4825405B2 (ja) * | 2003-05-08 | 2011-11-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | フォトレジスト組成物およびそれらの調製方法 |
| DE602004008468T2 (de) * | 2003-06-26 | 2008-05-21 | Jsr Corp. | Photoresistzusammensetzungen |
| US7250475B2 (en) | 2003-06-26 | 2007-07-31 | Symyx Technologies, Inc. | Synthesis of photoresist polymers |
| WO2005000924A1 (en) | 2003-06-26 | 2005-01-06 | Symyx Technologies, Inc. | Photoresist polymers |
| JP2007526351A (ja) | 2003-06-26 | 2007-09-13 | シミックス・テクノロジーズ・インコーポレイテッド | リビングフリーラジカルプロセスにより調製した、アクリル酸またはメタクリル酸ベースのポリマー樹脂を有するフォトレジストポリマーおよび組成物 |
| US7408013B2 (en) * | 2003-09-23 | 2008-08-05 | Commonwealth Scientific And Industrial Research Organization | Low-polydispersity photoimageable polymers and photoresists and processes for microlithography |
| KR101057850B1 (ko) | 2004-04-08 | 2011-08-19 | 제이에스알 가부시끼가이샤 | 감방사선성 수지 조성물, 층간 절연막, 마이크로 렌즈 및이들의 제조 방법 |
| WO2005108458A1 (ja) | 2004-05-06 | 2005-11-17 | Jsr Corporation | 硬化性樹脂組成物、保護膜およびその形成方法 |
-
2004
- 2004-09-16 US US10/943,063 patent/US7696292B2/en active Active
- 2004-09-22 EP EP10010041A patent/EP2287671B1/en not_active Expired - Lifetime
- 2004-09-22 DE DE602004032151T patent/DE602004032151D1/de not_active Expired - Lifetime
- 2004-09-22 CN CNA2004800271370A patent/CN1853139A/zh active Pending
- 2004-09-22 WO PCT/US2004/031242 patent/WO2005031461A1/en not_active Ceased
- 2004-09-22 EP EP04784900A patent/EP1664927B1/en not_active Expired - Lifetime
- 2004-09-22 TW TW093128730A patent/TW200525292A/zh unknown
- 2004-09-22 KR KR1020067005581A patent/KR101238580B1/ko not_active Expired - Fee Related
- 2004-09-22 JP JP2006528161A patent/JP2007520587A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641245A (ja) * | 1992-07-24 | 1994-02-15 | Shin Etsu Chem Co Ltd | 単分散性共重合体及びその製造方法 |
| JP2000515181A (ja) * | 1996-07-10 | 2000-11-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | リビング特性を持つ重合 |
| JP2002508409A (ja) * | 1997-12-18 | 2002-03-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | リビング性を有する重合方法およびその方法で製造されるポリマー |
| JP2001154362A (ja) * | 1999-11-29 | 2001-06-08 | Central Glass Co Ltd | ポジ型レジスト組成物およびパターン形成方法 |
| JP2003040840A (ja) * | 2001-07-24 | 2003-02-13 | Central Glass Co Ltd | 含フッ素重合性単量体およびそれを用いた高分子化合物 |
| JP2004038141A (ja) * | 2002-03-01 | 2004-02-05 | Shipley Co Llc | フォトレジスト組成物 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007091882A (ja) * | 2005-09-29 | 2007-04-12 | Jsr Corp | 樹脂の合成法 |
| JP2016026313A (ja) * | 2011-02-04 | 2016-02-12 | 日立化成株式会社 | 樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
| JP2015135492A (ja) * | 2013-12-31 | 2015-07-27 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | フォトレジストオーバーコート組成物 |
| WO2019181228A1 (ja) * | 2018-03-19 | 2019-09-26 | 株式会社ダイセル | フォトレジスト用樹脂、フォトレジスト用樹脂の製造方法、フォトレジスト用樹脂組成物、及びパターン形成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2287671A1 (en) | 2011-02-23 |
| TW200525292A (en) | 2005-08-01 |
| KR20060119985A (ko) | 2006-11-24 |
| WO2005031461A1 (en) | 2005-04-07 |
| EP1664927A1 (en) | 2006-06-07 |
| US7696292B2 (en) | 2010-04-13 |
| EP1664927B1 (en) | 2011-04-06 |
| DE602004032151D1 (de) | 2011-05-19 |
| CN1853139A (zh) | 2006-10-25 |
| EP2287671B1 (en) | 2012-06-06 |
| US20050119378A1 (en) | 2005-06-02 |
| KR101238580B1 (ko) | 2013-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3672780B2 (ja) | ポジ型レジスト組成物およびパターン形成方法 | |
| US8034534B2 (en) | Fluorinated polymers for use in immersion lithography | |
| KR101238580B1 (ko) | 저-다분산성 광형상화가능한 아크릴 중합체, 포토레지스트및 마이크로리소그래피 방법 | |
| KR101764443B1 (ko) | ArF 액침 노광용 화학 증폭 포지티브형 레지스트 재료 및 패턴 형성 방법 | |
| US7993810B2 (en) | (Meth)acrylate compound having aromatic acid labile group, photosensitive polymer, resist composition, and associated methods | |
| JP3749674B2 (ja) | バックボーンにラクトンが含まれた感光性ポリマーよりなるレジスト組成物 | |
| JP2009074085A (ja) | ポジ型レジスト組成物 | |
| JP2009029802A (ja) | 含フッ素化合物、含フッ素高分子化合物、ネガ型レジスト組成物及びそれを用いたパターン形成方法 | |
| JP2007511785A (ja) | 二酸化炭素中で調製され、堆積され、現像されかつ除去されるフッ化フォトレジスト | |
| US7282549B2 (en) | Fluorine-containing compounds, fluorine-containing polymerizable monomers, fluorine-containing polymers, dissolution inhibitors, and resist compositions | |
| US7408013B2 (en) | Low-polydispersity photoimageable polymers and photoresists and processes for microlithography | |
| JP4683887B2 (ja) | ラクトン化合物、ラクトン含有単量体、高分子化合物、それを用いたレジスト材料及びパターン形成方法 | |
| JP6468139B2 (ja) | 単量体、高分子化合物、レジスト材料及びパターン形成方法 | |
| JP6613615B2 (ja) | 高分子化合物及び単量体並びにレジスト材料及びパターン形成方法 | |
| JP2000007730A (ja) | 環状の背骨を有する感光性ポリマー及びこれを含むレジスト組成物 | |
| JP6908816B2 (ja) | 含フッ素単量体、それを用いた含フッ素重合体、それを用いた化学増幅型レジストおよびそれを用いたパターン形成方法 | |
| US8017301B2 (en) | Photosensitive polymer, resist composition, and associated methods | |
| JP6717338B2 (ja) | 高分子化合物、レジスト材料及びパターン形成方法 | |
| KR100732285B1 (ko) | 포토레지스트 단량체, 그의 중합체 및 이를 함유하는포토레지스트 조성물 | |
| JP2005099856A (ja) | ポジ型レジスト組成物 | |
| KR100889284B1 (ko) | 락톤 화합물, 락톤 함유 단량체, 그의 중합체, 그를 이용한레지스트 조성물 및 그를 이용한 패턴 형성방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070810 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070810 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20080627 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100226 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100625 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100924 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101001 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101022 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101029 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101125 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101202 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110301 |