JP2011081340A - 新規の樹脂およびこれを含むフォトレジスト組成物 - Google Patents
新規の樹脂およびこれを含むフォトレジスト組成物 Download PDFInfo
- Publication number
- JP2011081340A JP2011081340A JP2010115691A JP2010115691A JP2011081340A JP 2011081340 A JP2011081340 A JP 2011081340A JP 2010115691 A JP2010115691 A JP 2010115691A JP 2010115691 A JP2010115691 A JP 2010115691A JP 2011081340 A JP2011081340 A JP 2011081340A
- Authority
- JP
- Japan
- Prior art keywords
- photoresist
- groups
- resin
- present
- photoresist composition
- 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.)
- Granted
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 229920005989 resin Polymers 0.000 title claims abstract description 37
- 239000011347 resin Substances 0.000 title claims abstract description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 230000005855 radiation Effects 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000011247 coating layer Substances 0.000 claims description 11
- 230000003213 activating effect Effects 0.000 claims description 9
- 239000010410 layer Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 4
- 229920001897 terpolymer Polymers 0.000 claims description 2
- 229920006029 tetra-polymer Polymers 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- 125000002723 alicyclic group Chemical group 0.000 description 24
- -1 salt compounds Chemical class 0.000 description 21
- 125000004185 ester group Chemical group 0.000 description 19
- 239000000243 solution Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 11
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 150000002596 lactones Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002837 carbocyclic group Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000000686 lactone group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004036 acetal group Chemical group 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical compound [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 3
- 239000012953 triphenylsulfonium Substances 0.000 description 3
- 0 **(C1CO2)C(CC3OC(*)=O)OC3C1C2=O Chemical compound **(C1CO2)C(CC3OC(*)=O)OC3C1C2=O 0.000 description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 2
- ZOMPBXWFMAJRRU-UHFFFAOYSA-N 3-ethyloxiran-2-one Chemical group CCC1OC1=O ZOMPBXWFMAJRRU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 101000987219 Sus scrofa Pregnancy-associated glycoprotein 1 Proteins 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000002178 anthracenyl group Chemical class C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 230000003667 anti-reflective effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution 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
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 description 2
- 125000005561 phenanthryl group Chemical class 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GCIYMCNGLUNWNR-UHFFFAOYSA-N (2,4-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GCIYMCNGLUNWNR-UHFFFAOYSA-N 0.000 description 1
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical class C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 1
- GQRTVVANIGOXRF-UHFFFAOYSA-N (2-methyl-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)C2(OC(=O)C=C)C3 GQRTVVANIGOXRF-UHFFFAOYSA-N 0.000 description 1
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 1
- FFKFRQVYUILJCW-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;methanesulfonic acid Chemical class CS(O)(=O)=O.ON1C(=O)CCC1=O FFKFRQVYUILJCW-UHFFFAOYSA-N 0.000 description 1
- QPAWHGVDCJWYRJ-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;trifluoromethanesulfonic acid Chemical class ON1C(=O)CCC1=O.OS(=O)(=O)C(F)(F)F QPAWHGVDCJWYRJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- YXZXRYDYTRYFAF-UHFFFAOYSA-M 4-methylbenzenesulfonate;triphenylsulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 YXZXRYDYTRYFAF-UHFFFAOYSA-M 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102100024003 Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 1 Human genes 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- FFGZPMPKVPCQAG-UHFFFAOYSA-L C(C(O)C)(=O)[O-].[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC Chemical group C(C(O)C)(=O)[O-].[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC FFGZPMPKVPCQAG-UHFFFAOYSA-L 0.000 description 1
- DQQYSPCUHNCXAO-UHFFFAOYSA-N CCC(OCC(OC(C1)C2OC1C(CO1)C2C1=O)=O)=O Chemical compound CCC(OCC(OC(C1)C2OC1C(CO1)C2C1=O)=O)=O DQQYSPCUHNCXAO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 101100380306 Homo sapiens ASAP1 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 101150003633 PAG2 gene Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YPPVLYIFEAESGO-UHFFFAOYSA-N [2,3-bis(methylsulfonyloxy)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC(OS(C)(=O)=O)=C1OS(C)(=O)=O YPPVLYIFEAESGO-UHFFFAOYSA-N 0.000 description 1
- OIHCCWXZFYNOJS-UHFFFAOYSA-N [2,3-bis-(4-methylphenyl)sulfonyloxyphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C=2C=CC(C)=CC=2)=C1OS(=O)(=O)C1=CC=C(C)C=C1 OIHCCWXZFYNOJS-UHFFFAOYSA-N 0.000 description 1
- HKKMPPDCCCBZHM-UHFFFAOYSA-M [4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 HKKMPPDCCCBZHM-UHFFFAOYSA-M 0.000 description 1
- QFKJMDYQKVPGNM-UHFFFAOYSA-N [benzenesulfonyl(diazo)methyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=CC=C1 QFKJMDYQKVPGNM-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229920006109 alicyclic polymer Polymers 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 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
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
- 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
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
本発明は、本明細書において開示されるラクトン基および/または樹脂を含む光像形成性(photoimageable)組成物(すなわち、活性化放射線に対するパターン様露光、場合によって熱処理;現像を含むリソグラフィー処理によってレリーフ像を形成できる)も含む。
本発明の他の形態は以下で論じられる。
ある形態においては、本発明の樹脂の好ましい追加の単位には、ヘテロ置換(特にヒドロキシおよびチオ)炭素環式アリール部分、例えば、ヒドロキシナフチル基が挙げられる。本明細書において、ヘテロ置換炭素環式アリール基についての言及は、ヘテロ原子、特に酸素または硫黄を含む環置換基を1以上、典型的には1、2または3つ、その炭素環式基が有することを意味する。すなわち、「ヘテロ置換」についてのこのような言及は、1以上のヘテロ原子、とくに1もしくは2つの酸素および/または硫黄原子を含み、かつ炭素環式アリール基の環置換基である部分を指す。
好ましいポリマーは、ラクトン単位、例えば、重合されたアクリラートの部分であるラクトン、または他の不飽和分子から重合された他のラクトンも含むことができる。アルファ−ブチロラクトン基を含むポリマー単位が好適である。
本発明の好ましいポリマーは、2、3、4または5種、またはそれより多い異なる繰り返し単位を含み、すなわち、本明細書において開示されるラクトン基を1種以上含むコポリマー、ターポリマー、テトラポリマーおよびペンタポリマーが好ましい。
本発明のポリマーは脂環式部分を含まない光酸不安定基を含むこともできる。例えば、本発明のポリマーは光酸不安定アルキルエステルのような光酸不安定エステル単位を含むことができる。一般に、光酸不安定エステルのカルボキシル酸素(すなわち、−C(=O)−Oの下線が付されたカルボキシル酸素)は第四級炭素と共有結合されうる。t−ブチルおよび−C(CH3)2CH(CH3)2のような分岐光酸不安定エステルが一般に好ましい。
この点において、上述したように、本発明のレジストにおいて使用されるポリマーは異なる複数種の光酸不安定基を含むことができ、すなわち、そのポリマーは、例えば、一方のエステルが脂環式部分を有することができ、他方のエステルがt−ブチルのような非環式部分を有することができる、異なるエステル部分の置換を有する2種以上のエステル基を含むことができか、またはそのポリマーはエステル官能基と、アセタール、ケタールおよび/もしくはエーテルのような光酸不安定な他の官能基との双方を含むことができる。
好ましいアルカノイル基は、1以上のケト基、例えば、式−C(=O)R”;(式中、R”は水素またはC1−8アルキルである)の基を有しうる。
樹脂成分は、レジストの塗膜層を水性アルカリ現像剤で現像可能にするのに充分な量で使用されるべきである。
他の公知のPAGも本発明のレジストに使用されうる。特に、193nmでの像形成には、向上した透明性を提供するために、芳香族基を含まないPAG、例えば、上述のイミドスルホナートが一般的に好ましい。
反応は窒素環境下で行われた。氷浴を用いて0℃に冷却された乾燥ジメチルホルムアミド(DMF)(50mL)中のNaBH4(2.5g;1.1当量;66.2mmol)の攪拌された懸濁物に、無水物化合物1(10g、60.2mmol)を温度を0℃に維持するような速度で少しずつ添加した。その添加後、氷浴が取り外され、混合物をさらに3時間攪拌した。攪拌しつつ、6NのHCl(20mL)を注意深く添加し、その混合物を減圧下で濃縮した。水(100mL)を添加し、生成物を塩化メチレン(3回)で抽出し、有機層を水で3回洗浄し、硫酸マグネシウムで乾燥させ、高真空を用いて溶媒を除去し、化合物2の白色固体(7.1g、収率76%)を生じさせた。
全てのガラスは100℃でオーブン乾燥させられた。反応は窒素下で行われた。ラクトン2(2g、12mmol)を15mLのテトラヒドロフラン中で、室温で、30分間攪拌し、次いで温度を0℃に下げた。1MのBH3−THF錯体(4mL)を、0℃の温度を維持するような速度でこのラクトン溶液に滴下添加した。この添加後、この混合物を0℃で3分間攪拌し、室温で4時間攪拌した。
この混合物に3NのNaOH水溶液(4mL)を添加し、次いで過酸化水素(30%水溶液を4mL)をゆっくり添加した。この添加後、反応混合物を50℃で1.5時間攪拌した。この反応混合物を炭酸カリウムで飽和させ、2層が認められ、この2層を分けて、水性層をTHFで抽出した。合わせたTHF溶液を飽和NaClで洗浄し、溶媒を減圧下で除去して、白色半固体生成物を生じさせ、これをクロマトグラフィーで精製した(溶離剤として、塩化メチレン中5%メタノール);1.0g(収率50%)。
ヒドロキシラクトン3(6.0g、35.3mmol)を360mLのTHFに室温で(30分)溶解させ、これにトリエチルアミン(1.2当量、42.4mmol、4.3g)を添加し、次いで、この混合物を0℃に冷却した。これに、20mLのTHFに溶解されたメタアクリロイルクロライド(1.2当量、42.4mmol、4.4g)の溶液を滴下添加した。この添加後、この混合物を室温で一晩攪拌した。白色塩がろ別され、濾液から溶媒を蒸発させて生成物4(6.75g、収率82%)を得た。
ヒドロキシラクトン4(6.0g、35.3mmol)を360mLのTHFに室温(30分)で溶解させ、これにトリエチルアミン(1.2当量、42.4mmol、4.3g)を添加し、次いで、この混合物を0℃に冷却した。これに、20mLのTHFに溶解されたメタアクリロイルクロライド(1.2当量、42.4mmol、4.4g)の溶液を滴下添加した。この添加後、この混合物を室温で一晩攪拌した。白色塩がろ別され、濾液から溶媒を蒸発させて生成物5(6.75g、収率82%)を得た。
ODOT−OH(1)(30g、176mmol)をCH2Cl2(50mL)に懸濁した。クロロアセトルクロライド(21.9g、194mmol)を添加し、続いてDBU(32.3g、212mmol)を添加した。この混合物を室温で一晩おいた。標準の水性仕上げは褐色固体として、クルード化合物2を生じさせ、これはさらなる精製なしに次の工程で使用された。
PAG1:トリフェニルスルホニウムペルフルオロブタンスルホナート
PAG2:トリフェニルスルホニウムアダマンチルカルボニルジフルオロメチルスルホナート
塩基1:NACL
塩基2:N,N−ジエタノールドデシルアミン
溶媒1:プロピレングリコールメチルエーテルアセタート
溶媒2:シクロヘキサノン
1)Siウェハ上に有機反射防止組成物をコーティングし、205℃で60秒間ベークする。
2)ポリマー1〜3(4.788部)と、NACL(0.012部)と、溶媒1(37.600部)と、溶媒2(37.600部)との混合物を、工程1)の基体に適用し、1200Aの膜を形成させ、105℃で60秒間ベークする。
3)PAG1(0.524部)と、t−ブチルアクリラートおよびメタクリル酸のコポリマー(30:70、Mw=10K)とを、デカン(11.892)および2−メチル−1−ブチノール(47.568)の混合溶媒中で混合する。この混合物を工程2)において形成された膜上に適用し、300Aの厚みを得る。
4)開始線量1mJ/cm2および増分0.2mJ/cm2で、オープンフレーム露光を使用し、105℃/60秒でPEBし、次いでTMAH2.38%溶液中で60秒間現像する。
5)20mJ/cm2での膜損失を測定する。膜損失は、ポリマーマトリックス中の酸拡散を決定するために使用される。より多くの膜損失はより速い酸拡散を示す。表1は正規化された拡散長さ(DL)を報告する。
Claims (10)
- 前記樹脂がコポリマー、ターポリマー、テトラポリマーまたはペンタポリマーである、請求項1または2に記載のフォトレジスト組成物。
- 前記フォトレジストが1種以上の光酸発生剤化合物と1種以上の光酸不安定基とを含む、請求項1〜3のいずれか1項に記載のフォトレジスト組成物。
- 前記フォトレジスト樹脂が、光酸不安定である前記エステルとは異なる第2の光酸不安定基を含む、請求項1〜4のいずれか1項に記載のフォトレジスト組成物。
- a)請求項1〜5のいずれか1項のフォトレジスト組成物の塗膜層を基体上に適用し;および
b)前記フォトレジスト組成物層を活性化放射線に露光し、露光されたフォトレジスト組成物塗膜層を現像する;
ことを含む、フォトレジストレリーフ像を提供する方法。 - 前記フォトレジスト層が、約193nmの波長を有する放射線に露光される、請求項6に記載の方法。
- 請求項9または10の樹脂を含む像形成性組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21665409P | 2009-05-20 | 2009-05-20 | |
US61/216,654 | 2009-05-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011081340A true JP2011081340A (ja) | 2011-04-21 |
JP5717984B2 JP5717984B2 (ja) | 2015-05-13 |
Family
ID=42238230
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010115691A Active JP5717984B2 (ja) | 2009-05-20 | 2010-05-19 | 新規の樹脂およびこれを含むフォトレジスト組成物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20110039210A1 (ja) |
EP (1) | EP2253647A1 (ja) |
JP (1) | JP5717984B2 (ja) |
KR (2) | KR20100125197A (ja) |
CN (1) | CN101943861B (ja) |
TW (1) | TWI425314B (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012173209A1 (ja) * | 2011-06-14 | 2012-12-20 | 三菱レイヨン株式会社 | アルコール化合物とその製造方法、ラクトン化合物の製造方法、(メタ)アクリル酸エステルとその製造方法、重合体とその製造方法、レジスト組成物とこれを用いた基板の製造方法 |
JP2014111550A (ja) * | 2012-12-05 | 2014-06-19 | Mitsubishi Rayon Co Ltd | 重合性単量体の製造方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111116606B (zh) * | 2020-01-14 | 2021-03-16 | 大连九信精细化工有限公司 | 一种制备4,10-二氧杂三环[5.2.1.0(2,6)]癸-8-烯-3-酮的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002234882A (ja) * | 2000-12-06 | 2002-08-23 | Mitsubishi Rayon Co Ltd | (メタ)アクリル酸エステル、その原料アルコール、および、それらの製造方法 |
JP2002308866A (ja) * | 2001-04-09 | 2002-10-23 | Mitsubishi Chemicals Corp | ラクトン構造を有する多環式化合物 |
JP2003345025A (ja) * | 2002-05-28 | 2003-12-03 | Everlight Usa Inc | 化学増幅型ホトレジスト組成物 |
US20040241569A1 (en) * | 2003-05-28 | 2004-12-02 | Everlight Usa, Inc. | Chemically-amplified resist compositions |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6596463B2 (en) | 2000-04-20 | 2003-07-22 | Shin-Etsu Chemical, Co., Ltd. | Ester compounds, polymers, resist compositions and patterning process |
US6306554B1 (en) | 2000-05-09 | 2001-10-23 | Shipley Company, L.L.C. | Polymers containing oxygen and sulfur alicyclic units and photoresist compositions comprising same |
KR100531535B1 (ko) * | 2000-12-06 | 2005-11-28 | 미츠비시 레이온 가부시키가이샤 | (메트)아크릴산 에스테르, 그 원료 알콜, 이들의 제조방법, 이 (메트)아크릴산 에스테르를 중합하여 수득되는중합체, 화학 증폭형 레지스트 조성물, 및 패턴 형성 방법 |
JP3991191B2 (ja) * | 2001-06-14 | 2007-10-17 | 信越化学工業株式会社 | ラクトン構造を有する新規(メタ)アクリレート化合物、重合体、フォトレジスト材料、及びパターン形成法 |
US6720430B2 (en) * | 2002-05-28 | 2004-04-13 | Everlight Usa, Inc. | Monomer for chemical amplified photoresist compositions |
US6639035B1 (en) * | 2002-05-28 | 2003-10-28 | Everlight Usa, Inc. | Polymer for chemical amplified photoresist compositions |
JP4622579B2 (ja) * | 2004-04-23 | 2011-02-02 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物及び(メタ)アクリル酸誘導体とその製法 |
JP4744113B2 (ja) * | 2004-09-02 | 2011-08-10 | ダイセル化学工業株式会社 | 液浸露光用フォトレジスト用高分子化合物の製造法 |
JP2006091762A (ja) * | 2004-09-27 | 2006-04-06 | Maruzen Petrochem Co Ltd | ポジ型感光性樹脂及び新規ジチオール化合物 |
TWI530759B (zh) * | 2005-01-24 | 2016-04-21 | 富士軟片股份有限公司 | 適用於浸漬曝光之正型光阻組成物及使用它之圖案形成方法 |
JP4498939B2 (ja) * | 2005-02-01 | 2010-07-07 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
US20090305161A1 (en) * | 2005-11-21 | 2009-12-10 | Jsr Corporation | Liquid immersion lithography |
KR100994873B1 (ko) * | 2006-03-06 | 2010-11-16 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 고분자 화합물 및 포지티브형 레지스트 재료 및 이를이용한 패턴 형성 방법 |
JP4784753B2 (ja) * | 2006-07-06 | 2011-10-05 | 信越化学工業株式会社 | 重合性エステル化合物、重合体、レジスト材料及びパターン形成方法 |
JP4857218B2 (ja) * | 2006-09-26 | 2012-01-18 | 富士フイルム株式会社 | ポジ型感光性組成物及びそれを用いたパターン形成方法 |
KR101035742B1 (ko) * | 2006-09-28 | 2011-05-20 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 신규 광산 발생제 및 이것을 이용한 레지스트 재료 및 패턴형성 방법 |
JP5151586B2 (ja) * | 2007-03-23 | 2013-02-27 | 住友化学株式会社 | フォトレジスト組成物 |
EP1975705B1 (en) * | 2007-03-28 | 2016-04-27 | FUJIFILM Corporation | Positive resist composition and pattern-forming method |
JP2009075311A (ja) * | 2007-09-20 | 2009-04-09 | Fujifilm Corp | ポジ型レジスト組成物及び該ポジ型レジスト組成物を用いたパターン形成方法 |
JP2009079121A (ja) * | 2007-09-26 | 2009-04-16 | Fujifilm Corp | 顔料分散組成物、光硬化性組成物、カラーフィルタ及びカラーフィルタの製造方法 |
CN101565486A (zh) * | 2008-04-21 | 2009-10-28 | 住友化学株式会社 | 聚合物和含有该聚合物的化学放大型抗蚀剂组合物 |
-
2010
- 2010-05-18 US US12/782,528 patent/US20110039210A1/en not_active Abandoned
- 2010-05-19 EP EP10163278A patent/EP2253647A1/en not_active Withdrawn
- 2010-05-19 JP JP2010115691A patent/JP5717984B2/ja active Active
- 2010-05-19 TW TW099115903A patent/TWI425314B/zh active
- 2010-05-20 KR KR1020100047555A patent/KR20100125197A/ko active Application Filing
- 2010-05-20 CN CN2010102337492A patent/CN101943861B/zh active Active
-
2017
- 2017-06-02 KR KR1020170068882A patent/KR102026633B1/ko active IP Right Grant
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002234882A (ja) * | 2000-12-06 | 2002-08-23 | Mitsubishi Rayon Co Ltd | (メタ)アクリル酸エステル、その原料アルコール、および、それらの製造方法 |
JP2002308866A (ja) * | 2001-04-09 | 2002-10-23 | Mitsubishi Chemicals Corp | ラクトン構造を有する多環式化合物 |
JP2003345025A (ja) * | 2002-05-28 | 2003-12-03 | Everlight Usa Inc | 化学増幅型ホトレジスト組成物 |
US20040241569A1 (en) * | 2003-05-28 | 2004-12-02 | Everlight Usa, Inc. | Chemically-amplified resist compositions |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012173209A1 (ja) * | 2011-06-14 | 2012-12-20 | 三菱レイヨン株式会社 | アルコール化合物とその製造方法、ラクトン化合物の製造方法、(メタ)アクリル酸エステルとその製造方法、重合体とその製造方法、レジスト組成物とこれを用いた基板の製造方法 |
JPWO2012173209A1 (ja) * | 2011-06-14 | 2015-02-23 | 三菱レイヨン株式会社 | アルコール化合物とその製造方法、ラクトン化合物の製造方法、(メタ)アクリル酸エステルとその製造方法、重合体とその製造方法、レジスト組成物とこれを用いた基板の製造方法 |
KR20150100966A (ko) | 2011-06-14 | 2015-09-02 | 미쯔비시 레이온 가부시끼가이샤 | 알코올 화합물과 그 제조 방법, 락톤 화합물의 제조 방법, (메트)아크릴산에스테르와 그 제조 방법, 중합체와 그 제조 방법, 레지스트 조성물과 이것을 사용한 기판의 제조 방법 |
KR101575943B1 (ko) * | 2011-06-14 | 2015-12-08 | 미쯔비시 레이온 가부시끼가이샤 | 알코올 화합물과 그 제조 방법, 락톤 화합물의 제조 방법, (메트)아크릴산에스테르와 그 제조 방법, 중합체와 그 제조 방법, 레지스트 조성물과 이것을 사용한 기판의 제조 방법 |
KR101632860B1 (ko) * | 2011-06-14 | 2016-06-22 | 미쯔비시 레이온 가부시끼가이샤 | 알코올 화합물과 그 제조 방법, 락톤 화합물의 제조 방법, (메트)아크릴산에스테르와 그 제조 방법, 중합체와 그 제조 방법, 레지스트 조성물과 이것을 사용한 기판의 제조 방법 |
JP2017048197A (ja) * | 2011-06-14 | 2017-03-09 | 三菱レイヨン株式会社 | アルコール化合物の製造方法、(メタ)アクリル酸エステルの製造方法、重合体の製造方法、レジスト組成物の製造方法、パターンが形成された基板の製造方法、化合物および重合体 |
US9823563B2 (en) | 2011-06-14 | 2017-11-21 | Mitsubishi Chemical Corporation | Alcohol compound and method for producing same, method for producing lactone compound, (meth)acrylate ester and method for producing same, polymer and method for producing same, and resist composition and method for producing substrate using same |
JP2018009023A (ja) * | 2011-06-14 | 2018-01-18 | 三菱ケミカル株式会社 | アルコール化合物、(メタ)アクリル酸エステル、重合体およびその製造方法、レジスト組成物、パターンが形成された基板の製造方法 |
JP2014111550A (ja) * | 2012-12-05 | 2014-06-19 | Mitsubishi Rayon Co Ltd | 重合性単量体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20110039210A1 (en) | 2011-02-17 |
KR102026633B1 (ko) | 2019-09-30 |
CN101943861A (zh) | 2011-01-12 |
JP5717984B2 (ja) | 2015-05-13 |
TWI425314B (zh) | 2014-02-01 |
EP2253647A1 (en) | 2010-11-24 |
KR20170066294A (ko) | 2017-06-14 |
KR20100125197A (ko) | 2010-11-30 |
CN101943861B (zh) | 2013-07-24 |
TW201106098A (en) | 2011-02-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5047502B2 (ja) | 樹脂混合物を含むフォトレジスト組成物 | |
JP4498690B2 (ja) | 新規樹脂およびそれを含有するフォトレジスト組成物 | |
JP5782283B2 (ja) | 新規のポリマーおよびフォトレジスト組成物 | |
JP6225126B2 (ja) | 新規の樹脂およびこれを含むフォトレジスト組成物 | |
JP5796054B2 (ja) | 新規なポリマーおよびフォトレジスト組成物 | |
JP5624833B2 (ja) | 感活性光線性又は感放射線性樹脂組成物、これを用いたレジスト膜、及び、パターン形成方法 | |
JP5830493B2 (ja) | 感活性光線性又は感放射線性樹脂組成物、それを用いた感活性光線性又は感放射線性膜、パターン形成方法及び半導体デバイスの製造方法 | |
KR102026633B1 (ko) | 신규 수지 및 이를 포함하는 포토레지스트 조성물 | |
JP2004524565A (ja) | 新規な共重合体及びフォトレジスト組成物 | |
JP2003248317A (ja) | 短波長イメージングのためのフォトレジスト組成物 | |
JP2005196101A (ja) | ポリマーおよびこれを含むフォトレジスト組成物 | |
JP2005508013A (ja) | 新規ポリマーおよびそれを含むフォトレジスト組成物 | |
JP2012155234A (ja) | 感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜、マスクブランクス、及びパターン形成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130517 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140709 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140716 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20141015 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141020 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20141117 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141120 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141216 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150302 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150318 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5717984 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |