JP2011043794A - 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
- JP2011043794A JP2011043794A JP2010115708A JP2010115708A JP2011043794A JP 2011043794 A JP2011043794 A JP 2011043794A JP 2010115708 A JP2010115708 A JP 2010115708A JP 2010115708 A JP2010115708 A JP 2010115708A JP 2011043794 A JP2011043794 A JP 2011043794A
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoresist composition
- ester
- resin
- ring
- 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 61
- 229920005989 resin Polymers 0.000 title claims abstract description 51
- 239000011347 resin Substances 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims description 42
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000004185 ester group Chemical group 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000003367 polycyclic group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- 239000011247 coating layer Substances 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 230000003213 activating effect Effects 0.000 claims description 9
- 239000010410 layer Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 229920006029 tetra-polymer Polymers 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 14
- 229920000642 polymer Polymers 0.000 description 42
- 125000002723 alicyclic group Chemical group 0.000 description 25
- -1 polycyclic ester Chemical class 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000002837 carbocyclic group Chemical class 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 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
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000004036 acetal group Chemical group 0.000 description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 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
- 239000000654 additive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000006467 substitution reaction Methods 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
- 0 C*C(CCCC*)(c1ccccc1)OC(*C)=O Chemical compound C*C(CCCC*)(c1ccccc1)OC(*C)=O 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 238000003776 cleavage reaction Methods 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
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical compound [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 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 group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical group CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 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
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 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
- 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 1
- UVYTVJJBCFUXOS-UHFFFAOYSA-M 1,1-difluoro-2-[(3-hydroxy-1-adamantyl)oxy]-2-oxoethanesulfonate;triphenylsulfanium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1.C1C(C2)CC3CC1(O)CC2(OC(=O)C(F)(F)S([O-])(=O)=O)C3 UVYTVJJBCFUXOS-UHFFFAOYSA-M 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
- NKFNBVMJTSYZDV-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)amino]ethanol Chemical group CCCCCCCCCCCCN(CCO)CCO NKFNBVMJTSYZDV-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
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-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
- 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
- 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
- 229910001218 Gallium arsenide Inorganic materials 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
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 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
- 230000000996 additive effect Effects 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
- 150000001450 anions Chemical class 0.000 description 1
- 230000003667 anti-reflective effect Effects 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
- 235000015241 bacon Nutrition 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 238000009792 diffusion process Methods 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
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 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
- 125000003709 fluoroalkyl group Chemical group 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
- 239000011521 glass Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 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
- 125000000686 lactone group Chemical group 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 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
- 125000003518 norbornenyl group Chemical class C12(C=CC(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
- 230000002085 persistent effect Effects 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
- 230000008569 process Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 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
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 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
- 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
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
【解決手段】この新規樹脂を含む化学増幅ポジ型フォトレジスト、並びに複数環の芳香族および/または多環式エステルモノマーの提供。
【選択図】なし
Description
例えば、現在のレジストの持続している欠点は、特にポジ型レジストを使用する場合の「孤立した」レジスト線または他のフィーチャーの低い解像度である。現像されたレジスト線または他のフィーチャーは、それが最も近い隣のレジストフィーチャーから、その線幅の2倍以上の距離で離れている場合には、一般的に「孤立している」と見なされる。よって、例えば、ある線が0.25μm幅で印刷される場合に、その線は、その隣のレジストフィーチャーがその線から少なくとも約0.50ミクロンの間隔を開けられている場合には、孤立している(密集しているのではなく)と見なされるであろう。孤立した線について共通する解像度の問題としては、丸まった頂部およびアンダーカットが挙げられる。
理論に拘束されないが、リソグラフィー処理で遊離する(すなわち、当該基の光酸誘起切断)嵩高な脱離基(すなわち、多環式または芳香族基)は、レジスト層内により多くの自由体積を作り出すことができ、これは次いで、露光されたレジスト領域における光酸の所望のより多くの移動を促進することができ、一方で、未露光領域において留まっている嵩高な脱離基は、このような露光されたレジスト層領域への光酸の望まれない拡散を阻害することができ、それにより、コントラストおよびリソグラフィー結果を向上させることができると考えられる。すなわち、脱離基の比較的大きな立体サイズが、レジストに高い溶解コントラストを付与しうると考えられる。
さらに、第2の分岐点(すなわち、光酸誘起切断を受けない第2の環)の存在が脱離基の再結合速度を低下させることができ、それにより、フォトスピード(photospeed)を増大させ、および/または処理温度(すなわち、露光後ベーク温度)を低減させることができると考えられる。
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。
一形態においては、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。本明細書における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、こ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、特に1もしくは2つの酸素および/または硫黄原子を含み、炭素環式アリール基の環置換基である部分を指定する。
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種の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複数環の多環式エステル基を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るか、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。
本発明のレジストが下記成分を添加することにより製造される:量は固形分(溶媒を除いた全成分)の重量パーセントとして表され、そのレジストは下記の量で下記成分を混合することにより配合される:
配合したレジスト組成物はHMDS蒸気下塗り(primed)シリコンウェハ上にスピンコートされ、110℃で60秒間真空ホットプレートでソフトベークされる。このレジスト塗膜層がフォトマスクを通して193nmで露光され、次いで、露光された塗膜層が95℃で60秒間露光後ベークされる。像形成されたレジスト層が次いで、0.26Nの水性テトラメチルアンモニウムヒドロキシド溶液で処理することにより現像される。
本発明の上記記載は単にその例示であり、特許請求の範囲に示された発明の意図または範囲を逸脱することなく、変化および変更がなされうることが理解される。
Claims (15)
- 複数環の多環式エステル単位を含む樹脂を含むフォトレジスト組成物。
- 複数環のエステル単位を含む樹脂を含むフォトレジスト組成物であって、当該エステル単位の少なくとも1つの環が芳香族である、フォトレジスト組成物。
- 前記エステルのベータ炭素が芳香族または第四級である、請求項1または2に記載のフォトレジスト組成物。
- 保護されたアルカリ可溶性基を含む構造単位を含む膜形成性化合物を含むフォトレジスト組成物であって、前記単位における保護されたアルカリ可溶性基の保護部分は、光酸発生剤から生じる酸の作用によって切断されることができ、
前記保護部分は下記式VまたはVI:
の基を含む、フォトレジスト組成物。 - 前記アルカリ可溶性基が、カルボン酸基、スルホン酸基、アミド基、イミド基、フェノール基、チオール基、アザラクトン基およびヒドロキシオキシム基からなる群から選択される、請求項6に記載のフォトレジスト組成物。
- 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1〜7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が1種以上の光酸発生剤化合物を含み、エステル基が光酸不安定である、請求項1〜8のいずれか1項に記載のフォトレジスト組成物。
- 前記光酸不安定であるエステルとは異なる第2の光酸不安定基を、前記フォトレジスト樹脂が含む、請求項1〜9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1〜10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て、前記露光されたフォトレジスト塗膜層を現像する;
ことを含む、フォトレジストレリーフ像を提供する方法。 - (i)複数環の多環式エステル単位および/または(ii)複数環のエステル単位の少なくとも1つの環が芳香族である、当該複数環のエステル単位;を含む樹脂。
- 前記エステルのベータ炭素が芳香族または第四級である、請求項12に記載の樹脂。
- 請求項12〜14のいずれか1項の樹脂または化合物を含む像形成性組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21666009P | 2009-05-20 | 2009-05-20 | |
US61/216,660 | 2009-05-20 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015000591A Division JP6225126B2 (ja) | 2009-05-20 | 2015-01-05 | 新規の樹脂およびこれを含むフォトレジスト組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011043794A true JP2011043794A (ja) | 2011-03-03 |
JP5735220B2 JP5735220B2 (ja) | 2015-06-17 |
Family
ID=42711661
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010115708A Active JP5735220B2 (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 |
JP2015000591A Active JP6225126B2 (ja) | 2009-05-20 | 2015-01-05 | 新規の樹脂およびこれを含むフォトレジスト組成物 |
JP2017130636A Withdrawn JP2017223958A (ja) | 2009-05-20 | 2017-07-03 | 新規の樹脂およびこれを含むフォトレジスト組成物 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015000591A Active JP6225126B2 (ja) | 2009-05-20 | 2015-01-05 | 新規の樹脂およびこれを含むフォトレジスト組成物 |
JP2017130636A Withdrawn JP2017223958A (ja) | 2009-05-20 | 2017-07-03 | 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) | US20110039206A1 (ja) |
EP (1) | EP2293143B1 (ja) |
JP (3) | JP5735220B2 (ja) |
KR (2) | KR20100125198A (ja) |
CN (1) | CN101950127B (ja) |
TW (2) | TWI468857B (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013133230A1 (ja) * | 2012-03-06 | 2013-09-12 | Jsr株式会社 | フォトレジスト組成物、レジストパターン形成方法、重合体及び化合物 |
JP2014081633A (ja) * | 2012-09-28 | 2014-05-08 | Jsr Corp | フォトレジスト組成物、レジストパターン形成方法、重合体及び化合物 |
JP2015184389A (ja) * | 2014-03-20 | 2015-10-22 | 東京応化工業株式会社 | 化学増幅型ポジ型感光性樹脂組成物 |
US9874816B2 (en) | 2013-09-26 | 2018-01-23 | Jsr Corporation | Radiation-sensitive resin composition and resist pattern-forming method |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011060655A (ja) * | 2009-09-11 | 2011-03-24 | Panasonic Corp | リチウム電池 |
TWI646397B (zh) * | 2015-10-31 | 2019-01-01 | 南韓商羅門哈斯電子材料韓國公司 | 與外塗佈光致抗蝕劑一起使用的塗料組合物 |
JP6999351B2 (ja) * | 2017-10-05 | 2022-01-18 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、高分子化合物及び化合物 |
KR20200031257A (ko) * | 2018-09-14 | 2020-03-24 | 도오꾜오까고오교 가부시끼가이샤 | 레지스트 조성물 및 레지스트 패턴 형성 방법 |
US11829068B2 (en) | 2020-10-19 | 2023-11-28 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, compound, and resin |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002003537A (ja) * | 2000-04-20 | 2002-01-09 | Shin Etsu Chem Co Ltd | 新規なエステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 |
JP2005097533A (ja) * | 2003-09-03 | 2005-04-14 | Shin Etsu Chem Co Ltd | 高分子化合物、レジスト材料及びパターン形成方法 |
JP2008083385A (ja) * | 2006-09-27 | 2008-04-10 | Fujifilm Corp | 感光性組成物及びそれを用いたパターン形成方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000029216A (ja) * | 1998-07-09 | 2000-01-28 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
JP3879815B2 (ja) * | 2000-04-20 | 2007-02-14 | 信越化学工業株式会社 | 新規なエステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 |
KR100582158B1 (ko) * | 2000-04-20 | 2006-05-23 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 신규한 에스테르 화합물, 고분자 화합물, 레지스트 재료및 패턴 형성 방법 |
JP3997382B2 (ja) * | 2000-04-28 | 2007-10-24 | 信越化学工業株式会社 | 脂環構造を有する新規エステル化合物及びその製造方法 |
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 |
JP4243859B2 (ja) * | 2003-09-12 | 2009-03-25 | 信越化学工業株式会社 | 高分子化合物、レジスト材料、及びパターン形成方法 |
US7601479B2 (en) * | 2003-09-12 | 2009-10-13 | Shin-Etsu Chemical Co., Ltd. | Polymer, resist composition and patterning process |
JP4539847B2 (ja) * | 2004-04-09 | 2010-09-08 | 信越化学工業株式会社 | ポジ型レジスト材料並びにこれを用いたパターン形成方法 |
JP4300420B2 (ja) * | 2004-06-21 | 2009-07-22 | 信越化学工業株式会社 | 高分子化合物、レジスト材料及びパターン形成方法 |
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 |
KR101156975B1 (ko) * | 2005-06-24 | 2012-06-20 | 주식회사 동진쎄미켐 | 포토레지스트용 폴리머 및 이를 포함하는 포토레지스트 조성물 |
CN1928719A (zh) * | 2005-09-07 | 2007-03-14 | 北京科华微电子材料有限公司 | 具有多环内脂结构单元的聚合物在深紫外光刻胶中的应用 |
JP4697443B2 (ja) * | 2005-09-21 | 2011-06-08 | 信越化学工業株式会社 | ポジ型レジスト材料並びにこれを用いたパターン形成方法 |
US7629106B2 (en) * | 2005-11-16 | 2009-12-08 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process using the same |
JP5012073B2 (ja) * | 2006-02-15 | 2012-08-29 | 住友化学株式会社 | フォトレジスト組成物 |
KR100994873B1 (ko) * | 2006-03-06 | 2010-11-16 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 고분자 화합물 및 포지티브형 레지스트 재료 및 이를이용한 패턴 형성 방법 |
US7569326B2 (en) * | 2006-10-27 | 2009-08-04 | Shin-Etsu Chemical Co., Ltd. | Sulfonium salt having polymerizable anion, polymer, resist composition, and patterning process |
CN101256361B (zh) * | 2007-02-26 | 2011-12-28 | 新应材股份有限公司 | 光阻剂 |
JP4961324B2 (ja) * | 2007-10-26 | 2012-06-27 | 富士フイルム株式会社 | 電子線、x線又はeuv用ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
KR101606010B1 (ko) * | 2008-04-21 | 2016-03-24 | 스미또모 가가꾸 가부시키가이샤 | 중합체 및 이를 포함하는 화학 증폭형 레지스트 조성물 |
JP5136792B2 (ja) * | 2008-11-21 | 2013-02-06 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
TWI503334B (zh) * | 2009-02-19 | 2015-10-11 | Jsr Corp | 聚合物及敏輻射線性組成物、及單體 |
JP6241711B2 (ja) * | 2013-06-13 | 2017-12-06 | いすゞ自動車株式会社 | 車両のキャブロック構造 |
-
2010
- 2010-05-18 US US12/782,466 patent/US20110039206A1/en not_active Abandoned
- 2010-05-19 TW TW99115904A patent/TWI468857B/zh active
- 2010-05-19 EP EP10163283.4A patent/EP2293143B1/en not_active Not-in-force
- 2010-05-19 TW TW102123772A patent/TWI516863B/zh active
- 2010-05-19 JP JP2010115708A patent/JP5735220B2/ja active Active
- 2010-05-20 KR KR1020100047562A patent/KR20100125198A/ko active Application Filing
- 2010-05-20 CN CN2010102401925A patent/CN101950127B/zh active Active
-
2015
- 2015-01-05 JP JP2015000591A patent/JP6225126B2/ja active Active
-
2017
- 2017-07-03 JP JP2017130636A patent/JP2017223958A/ja not_active Withdrawn
-
2018
- 2018-11-14 KR KR1020180139621A patent/KR102013152B1/ko active IP Right Grant
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002003537A (ja) * | 2000-04-20 | 2002-01-09 | Shin Etsu Chem Co Ltd | 新規なエステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 |
JP2005097533A (ja) * | 2003-09-03 | 2005-04-14 | Shin Etsu Chem Co Ltd | 高分子化合物、レジスト材料及びパターン形成方法 |
JP2008083385A (ja) * | 2006-09-27 | 2008-04-10 | Fujifilm Corp | 感光性組成物及びそれを用いたパターン形成方法 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013133230A1 (ja) * | 2012-03-06 | 2013-09-12 | Jsr株式会社 | フォトレジスト組成物、レジストパターン形成方法、重合体及び化合物 |
JPWO2013133230A1 (ja) * | 2012-03-06 | 2015-07-30 | Jsr株式会社 | フォトレジスト組成物、レジストパターン形成方法、重合体及び化合物 |
JP2014081633A (ja) * | 2012-09-28 | 2014-05-08 | Jsr Corp | フォトレジスト組成物、レジストパターン形成方法、重合体及び化合物 |
US9874816B2 (en) | 2013-09-26 | 2018-01-23 | Jsr Corporation | Radiation-sensitive resin composition and resist pattern-forming method |
JP2015184389A (ja) * | 2014-03-20 | 2015-10-22 | 東京応化工業株式会社 | 化学増幅型ポジ型感光性樹脂組成物 |
Also Published As
Publication number | Publication date |
---|---|
JP5735220B2 (ja) | 2015-06-17 |
KR102013152B1 (ko) | 2019-08-22 |
KR20100125198A (ko) | 2010-11-30 |
JP6225126B2 (ja) | 2017-11-01 |
JP2015096620A (ja) | 2015-05-21 |
EP2293143B1 (en) | 2015-09-02 |
KR20180124007A (ko) | 2018-11-20 |
CN101950127A (zh) | 2011-01-19 |
JP2017223958A (ja) | 2017-12-21 |
CN101950127B (zh) | 2013-07-24 |
KR102013152B9 (ko) | 2023-08-16 |
TW201107881A (en) | 2011-03-01 |
TWI516863B (zh) | 2016-01-11 |
US20110039206A1 (en) | 2011-02-17 |
TW201341953A (zh) | 2013-10-16 |
EP2293143A3 (en) | 2011-03-23 |
TWI468857B (zh) | 2015-01-11 |
EP2293143A2 (en) | 2011-03-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
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 | |
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 | |
JP5047502B2 (ja) | 樹脂混合物を含む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 | |
JP6664440B2 (ja) | イオン性化合物を含むフォトレジスト | |
JP6040281B2 (ja) | 窒素含有化合物を含むフォトレジスト | |
JP5796054B2 (ja) | 新規なポリマーおよびフォトレジスト組成物 | |
KR102026633B1 (ko) | 신규 수지 및 이를 포함하는 포토레지스트 조성물 | |
KR20030076215A (ko) | 단파장 이미지화용 포토레지스트 조성물 | |
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 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130517 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140630 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140630 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140929 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141002 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20141029 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141104 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20141128 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141203 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150105 |
|
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: 20150330 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150416 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5735220 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 |