JP2005091976A - 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 - Google Patents
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 Download PDFInfo
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- JP2005091976A JP2005091976A JP2003327311A JP2003327311A JP2005091976A JP 2005091976 A JP2005091976 A JP 2005091976A JP 2003327311 A JP2003327311 A JP 2003327311A JP 2003327311 A JP2003327311 A JP 2003327311A JP 2005091976 A JP2005091976 A JP 2005091976A
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- Prior art keywords
- group
- alkyl group
- fluorine atom
- alicyclic hydrocarbon
- substituted
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 229920005989 resin Polymers 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 42
- 239000002253 acid Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 119
- -1 nitrogen-containing basic compound Chemical class 0.000 claims description 77
- 229910052731 fluorine Inorganic materials 0.000 claims description 60
- 125000001153 fluoro group Chemical group F* 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000002723 alicyclic group Chemical group 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 7
- 230000035945 sensitivity Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 42
- 239000002904 solvent Substances 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 32
- 239000004094 surface-active agent Substances 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 239000004215 Carbon black (E152) Substances 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 230000005855 radiation Effects 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 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 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- MXGIKIUCOFSUIB-UHFFFAOYSA-N C(C)(=O)OC(COC)C.C1(OCC(C)O1)=O Chemical compound C(C)(=O)OC(COC)C.C1(OCC(C)O1)=O MXGIKIUCOFSUIB-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000004185 ester group Chemical group 0.000 description 7
- 229940116333 ethyl lactate Drugs 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000005702 oxyalkylene group Chemical group 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- FKIVRAUTVLLGCD-UHFFFAOYSA-N 1,3-dioxolan-2-one 1-methoxypropan-2-yl acetate Chemical compound C(C)(=O)OC(COC)C.C1(OCCO1)=O FKIVRAUTVLLGCD-UHFFFAOYSA-N 0.000 description 6
- GCCURMRNGGCXDT-UHFFFAOYSA-N 1-methoxypropan-2-yl acetate;oxolan-2-one Chemical compound O=C1CCCO1.COCC(C)OC(C)=O GCCURMRNGGCXDT-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000006162 fluoroaliphatic group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 238000001312 dry etching Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000003504 photosensitizing agent Substances 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 125000000101 thioether group Chemical group 0.000 description 4
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- GQKDBQTXMIUPSY-UHFFFAOYSA-N 1-methoxypropan-2-ol;1-methoxypropan-2-yl acetate Chemical compound COCC(C)O.COCC(C)OC(C)=O GQKDBQTXMIUPSY-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 101000987219 Sus scrofa Pregnancy-associated glycoprotein 1 Proteins 0.000 description 2
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- USDUBSHTKGJFNL-UHFFFAOYSA-M [4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)phenyl]-diphenylsulfanium;bromide Chemical compound [Br-].C1=CC(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 USDUBSHTKGJFNL-UHFFFAOYSA-M 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical group C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- QKEUIMZDVADHSR-UHFFFAOYSA-N cyclohexanone 1-methoxypropan-2-yl acetate Chemical compound O=C1CCCCC1.COCC(C)OC(C)=O QKEUIMZDVADHSR-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
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- CYFIHPJVHCCGTF-UHFFFAOYSA-N prop-2-enyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC=C CYFIHPJVHCCGTF-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- ZQMAPKVSTSACQB-UHFFFAOYSA-N prop-2-enyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC=C ZQMAPKVSTSACQB-UHFFFAOYSA-N 0.000 description 1
- HAFZJTKIBGEQKT-UHFFFAOYSA-N prop-2-enyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC=C HAFZJTKIBGEQKT-UHFFFAOYSA-N 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical class [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UTLSPDKDSA-N ursocholic acid Chemical class C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-UTLSPDKDSA-N 0.000 description 1
- 238000005406 washing Methods 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
- G03F7/0046—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
- G03F7/039—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/126—Halogen compound containing
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
【解決手段】 (A)酸の作用によりアルカリ現像液に対する溶解度が増大する樹脂及び
(B−1)特定構造の化合物
を含有する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。
【選択図】 なし
Description
(B−1)下記一般式(I)で表される化合物
を含有することを特徴とするポジ型レジスト組成物。
本発明のポジ型レジスト組成物は、酸の作用によりアルカリ現像液に対する溶解度が増大する樹脂を含有する。
上記式中、Rf、Rgは、水素原子、アルキル基、ハロゲン原子、水酸基、アルコキシ基を表し、両者は同一でも異なっていてもよい。アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基等の低級アルキル基が好ましく、更に好ましくはメチル基、エチル基、プロピル基、イソプロピル基から選択される。アルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基等の炭素数1〜4のものを挙げることができる。アルキル基、アルコキシ基は、更なる置換基を有していてもよい。アルキル基、アルコキシ基の更なる置換基としては、水酸基、ハロゲン原子、アルコキシ基を挙げることができる。ハロゲン原子としては、塩素原子、臭素原子、フッ素原子、沃素原子等を挙げることができる。r1は1〜10の整数である。
上記式中、Rnf、Rngは、水素原子、アルキル基、ハロゲン原子、水酸基、アルコキシ基を表し、両者は同一でも異なっていてもよい。アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基等の低級アルキル基が好ましく、更に好ましくはメチル基、エチル基、プロピル基、イソプロピル基から選択される。アルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基等の炭素数1〜4のものを挙げることができる。アルキル基、アルコキシ基は、更なる置換基を有していてもよい。アルキル基、アルコキシ基の更なる置換基としては、水酸基、ハロゲン原子、アルコキシ基を挙げることができる。ハロゲン原子としては、塩素原子、臭素原子、フッ素原子、沃素原子等を挙げることができる。rは1〜10の整数である。
(1)塗布溶剤に対する溶解性、
(2)製膜性(ガラス転移点)、
(3)アルカリ現像性、
(4)膜べり(親疎水性、アルカリ可溶性基選択)、
(5)未露光部の基板への密着性、
(6)ドライエッチング耐性、
等の微調整が可能となる。
アクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸アミル、アクリル酸シクロヘキシル、アクリル酸エチルヘキシル、アクリル酸オクチル、アクリル酸−t−オクチル、クロルエチルアクリレート、2−ヒドロキシエチルアクリレート2,2−ジメチルヒドロキシプロピルアクリレート、5−ヒドロキシペンチルアクリレート、トリメチロールプロパンモノアクリレート、ペンタエリスリトールモノアクリレート、ベンジルアクリレート、メトキシベンジルアクリレート、フルフリルアクリレート、テトラヒドロフルフリルアクリレート等。
メチルメタクリレート、エチルメタクリレート、プロピルメタクリレート、イソプロピルメタクリレート、アミルメタクリレート、ヘキシルメタクリレート、シクロヘキシルメタクリレート、ベンジルメタクリレート、クロルベンジルメタクリレート、オクチルメタクリレート、2−ヒドロキシエチルメタクリレート、4−ヒドロキシブチルメタクリレート、5−ヒドロキシペンチルメタクリレート、2,2−ジメチル−3−ヒドロキシプロピルメタクリレート、トリメチロールプロパンモノメタクリレート、ペンタエリスリトールモノメタクリレート、フルフリルメタクリレート、テトラヒドロフルフリルメタクリレート等。
アクリルアミド、N−アルキルアクリルアミド(アルキル基としては炭素数1〜10のもの、例えばメチル基、エチル基、プロピル基、ブチル基、t−ブチル基、ヘプチル基、オクチル基、シクロヘキシル基、ヒドロキシエチル基等がある。)、N,N−ジアルキルアクリルアミド(アルキル基としては炭素数1〜10のもの、例えばメチル基、エチル基、ブチル基、イソブチル基、エチルヘキシル基、シクロヘキシル基等がある)、N−ヒドロキシエチル−N−メチルアクリルアミド、N−2−アセトアミドエチル−N−アセチルアクリルアミド等。
メタクリルアミド、N−アルキルメタクリルアミド(アルキル基としては炭素数1〜10のもの、例えばメチル基、エチル基、t−ブチル基、エチルヘキシル基、ヒドロキシエチル基、シクロヘキシル基等がある)、N,N−ジアルキルメタクリルアミド(アルキル基としてはエチル基、プロピル基、ブチル基等がある)、N−ヒドロキシエチル−N−メチルメタクリルアミド等。
アリルエステル類(例えば酢酸アリル、カプロン酸アリル、カプリル酸アリル、ラウリン酸アリル、パルミチン酸アリル、ステアリン酸アリル、安息香酸アリル、アセト酢酸アリル、乳酸アリル等)、アリルオキシエタノール等。
アルキルビニルエーテル(例えばヘキシルビニルエーテル、オクチルビニルエーテル、デシルビニルエーテル、エチルヘキシルビニルエーテル、メトキシエチルビニルエーテル、エトキシエチルビニルエーテル、クロルエチルビニルエーテル、1−メチル−2,2−ジメチルプロピルビニルエーテル、2−エチルブチルビニルエーテル、ヒドロキシエチルビニルエーテル、ジエチレングリコールビニルエーテル、ジメチルアミノエチルビニルエーテル、ジエチルアミノエチルビニルエーテル、ブチルアミノエチルビニルエーテル、ベンジルビニルエーテル、テトラヒドロフルフリルビニルエーテル等。
ビニルブチレート、ビニルイソブチレート、ビニルトリメチルアセテート、ビニルジエチルアセテート、ビニルバレート、ビニルカプロエート、ビニルクロルアセテート、ビニルジクロルアセテート、ビニルメトキシアセテート、ビニルブトキシアセテート、ビニルアセトアセテート、ビニルラクテート、ビニル−β−フェニルブチレート、ビニルシクロヘキシルカルボキシレート等。
イタコン酸ジメチル、イタコン酸ジエチル、イタコン酸ジブチル等。
本発明のポジ型レジスト組成物は、活性光線又は放射線の照射により酸を発生する化合物として、下記一般式(I)で表される化合物を含有する。
本発明のポジ型レジスト組成物は、活性光線又は放射線の照射により酸を発生する化合物として、更に、下記一般式(II)又は(III)で表される化合物を含有することが好ましい。
本発明のポジ型レジスト組成物は、活性光線又は放射線の照射により酸を発生する化合物として、更に、他の化合物(光酸発生剤)を含有してもよい。
SiF6 2-、ClO4 -、CF3SO3 -等のパーフルオロアルカンスルホン酸アニオン、ペンタフルオロベンゼンスルホン酸アニオン、ナフタレン−1−スルホン酸アニオン等の縮合多核芳香族スルホン酸アニオン、アントラキノンスルホン酸アニオン、スルホン酸基含有染料等を挙げることができるがこれらに限定されるものではない。
本発明のポジ型レジスト組成物は、溶媒として混合溶剤を使用することが好ましい。この混合溶剤として、プロピレングリコールモノアルキルエーテルカルボキシレートの内の少なくとも1種(A群の溶剤ともいう)と、プロピレングリコールモノアルキルエーテル、乳酸アルキル及びアルコキシプロピオン酸アルキルの内の少なくとも1種(B群の溶剤ともいう)及び/又はγ−ブチロラクトン、エチレンカーボネート、プロピレンカーボネート及びシクロヘキサノンの内の少なくとも1種(C群の溶剤ともいう)とを含有する混合溶剤を挙げることができる。即ち、混合溶剤としては、A群の溶剤とB群の溶剤との組み合わせ、A群の溶剤とC群の溶剤との組み合わせ、A群の溶剤とB群の溶剤とC群の溶剤との組み合わせを用いることができる。
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート
プロピレングリコールモノメチルエーテルアセテート+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+シクロヘキサノン
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+シクロヘキサノン
である。
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート+γ−ブチロラクトン
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート+エチレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコールモノメチルエーテル+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+乳酸エチル+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+3−エトキシエチルプロピオネート+プロピレンカーボネート
プロピレングリコールモノメチルエーテルアセテート+プロピレングリコール
モノメチルエーテル+シクロヘキサノン
プロピレングリコールモノメチルエーテルアセテート+シクロヘキサノン
である。
次に本発明のポジ型レジスト組成物に好ましく使用することができる(D)含窒素塩基性化合物について説明する。(D)含窒素塩基性化合物としては、有機アミン、塩基性のアンモニウム塩、塩基性のスルホニウム塩などが用いられ、昇華やレジスト性能を劣化させないものであればよい。
本発明のポジ型レジスト組成物は、更に(E)フッ素系及び/又はシリコン系界面活性剤(フッ素系界面活性剤及びシリコン系界面活性剤、フッ素原子と珪素原子の両方を含有する界面活性剤)のいずれか、あるいは2種以上を含有することが好ましい。
本発明のポジ型レジスト組成物は、上記の成分を(C)溶媒に溶解し、フィルターで濾過し、次のように所定の支持体上に塗布して用いる。
2−エチル−2−アダマンチルメタクリレート、ブチロラクトンメタクリレートを55/45の割合で仕込みメチルエチルケトン/テトラヒドロフラン=5/5に溶解し、固形分濃度20質量%の溶液100mLを調製した。この溶液に和光純薬社製重合開始剤V−65を2mol%加え、これを窒素雰囲気下、4時間かけて60℃に加熱したメチルエチルケトン10mLに滴下した。滴下終了後、反応液を4時間加熱、再度和光純薬社製重合開始剤V−65を1mol%添加し、4時間攪拌した。反応終了後、反応液を室温まで冷却し、蒸留水/イソプロピルアルコール=1/1(質量比)の混合溶媒3Lに晶析、析出した白色粉体である樹脂(1)を回収した。
4-ノナフルオロブチルブロモベンゼン31.3g(0.075mol)から常法により調製されたグリニャール試薬のテトラヒドロフラン溶液に、ジフェニルスルホキシド6.1g(0.03mol)を添加した後、トリメチルシリルクロライド8.1g(0.075mol)を0〜30℃で滴下し、3時間攪拌した。反応終了後、得られた反応液を12%臭化水素酸100mlに注入し、トルエン75mlで洗浄した後、ジクロロメタン75mlで3回抽出した。得られた目的物を濃縮乾固し、酢酸エチル100mlを加えて晶析させ、4-ノナフルオロブチルフェニルジフェニルスルホニウムブロマイドを7.5g得た。
4-ブロモフルオロベンゼン31.3g(0.075mol)から常法により調製されたグリニャール試薬のテトラヒドロフラン溶液に、ジフェニルスルホキシド7.2g(0.03mol)を添加した後、トリメチルシリルクロライド8.1g(0.075mol)を20〜25℃で滴下し、3時間攪拌した。反応終了後、得られた反応液を12%臭化水素酸100mlに注入し、トルエン75mlで洗浄した後、ジクロロメタン75mlで3回抽出した。得られた目的物を濃縮乾固し、アセトン30mlを加えて晶析させ、トリス(4−フルオロフェニル)スルホニウムブロマイドを6.5g得た。
ジ(4−フルオロフェニル)スルホキシド7.2g(0.03mol)とフルオロベンゼン5.8g(0.06mol)をジクロロメタン50mlに溶解し、トリフルオロメタンスルホン酸無水物8.9g(0.315mol)を−78〜−80℃で滴下した。徐々に室温まで温度を上昇させて2時間攪拌反応させた。水洗、濃縮して得られた粗生成物を酢酸エチル/n−ヘキサン混合溶媒(3:1)で晶析させ、化合物(PAG−B)を8.8g得た。
(ポジ型レジスト組成物の調製と評価)
樹脂 1.03g、
光酸発生剤 0.00035mol、
含窒素塩基性化合物 1.65mg及び
界面活性剤 全体の100ppm
を表3に示すように配合し、それぞれ固形分が11質量%になるように表3に示す溶媒に溶解した後、0.1μmのミクロフィルターで濾過し、実施例1〜10と比較例1〜5のポジ型レジスト組成物を調製した。
N−1: 1,5−ジアザビシクロ[4.3.0]−5−ノネン
N−2: 1,8−ジアザビシクロ[5.4.0]−7−ウンデセン
N−3: 4−ジメチルアミノピリジン
N−4: トリフェニルイミダゾール
N−5: ジイソプロピルアニリン
N−6: トリブチルアミン
N−7: トリオクチルアミン
を表す。
W−1: メガファックF176(大日本インキ化学工業(株)製)(フッ素系)
W−2: メガファックR08(大日本インキ化学工業(株)製)(フッ素及びシリコーン系)
を表す。
S−1:プロピレングリコールモノメチルエーテルアセテート
S−2:乳酸エチル
S−3:酢酸ブチル
S−4:2−ヘプタノン
S−5:プロピレングリコールモノメチルエーテル
S−6:エトキシプロピオン酸エチル
S−7:γ−ブチロラクトン
S−8:エチレンカーボネート
S−9:プロピレンカーボネート
S−10:シクロヘキサノン
を表す。
スピンコーターにてヘキサメチルジシラザン処理を施したシリコンウエハ上にブリューワーサイエンス社製ARC29aを780オングストローム均一に塗布し、100℃で90秒間ホットプレート上で乾燥した後、205℃で60秒間加熱乾燥を行い、反射防止膜を形成させた。その後、調製直後の各ポジ型レジスト組成物をスピンコーターで塗布し120℃で90秒加熱し、0.30μmのレジスト膜を形成させた。
マスクに於ける0.15μmのラインパターンを再現する最小露光量により得られた0.15μmのラインパターンの断面形状を走査型電子顕微鏡により観察した。矩形状のものを○、ラウンドトップ形状のものを×、ややラウンドトップ形状のものを△で示した。
レジスト組成物を塗布し加熱して形成したレジスト膜に、0.15μmのラインアンドスペースパターンが設計どおりにパターン形成できる放射線照射量(例えば、ArFエキシマレーザー:30mJ/cm2)を照射し、放射線照射の工程までを行ったウェハーを、1時間クリーンルーム中に放置した。ついで放射線照射後の加熱に続いて現像し、0.15μmラインアンドスペースパターンの設計寸法からのずれを測定した。
|設計寸法−実寸法|(nm)
値が小さいほど良好であると判断した。
Claims (4)
- (A)酸の作用によりアルカリ現像液に対する溶解度が増大する樹脂及び
(B−1)下記一般式(I)で表される化合物
を含有することを特徴とするポジ型レジスト組成物。
- 更に、(B−2)下記一般式(II)又は(III)で表される化合物を含有することを特徴とする請求項1に記載のポジ型レジスト組成物。
- 更に、(C)含窒素塩基性化合物を含有することを特徴とする請求項1又は2に記載のポジ型レジスト組成物。
- 請求項1〜3のいずれかに記載のポジ型レジスト組成物によりレジスト膜を形成し、該レジスト膜を露光、現像する工程を含むことを特徴とするパターン形成方法。
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EP04022176A EP1519228A3 (en) | 2003-09-19 | 2004-09-17 | Positive resist composition and pattern formation method using the same |
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JP2012108527A (ja) * | 2006-01-24 | 2012-06-07 | Fujifilm Corp | 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 |
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-
2003
- 2003-09-19 JP JP2003327311A patent/JP4411042B2/ja not_active Expired - Lifetime
-
2004
- 2004-09-17 US US10/942,852 patent/US7285369B2/en active Active
- 2004-09-17 EP EP04022176A patent/EP1519228A3/en not_active Withdrawn
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Also Published As
Publication number | Publication date |
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US7285369B2 (en) | 2007-10-23 |
EP1519228A2 (en) | 2005-03-30 |
JP4411042B2 (ja) | 2010-02-10 |
US20050064329A1 (en) | 2005-03-24 |
EP1519228A3 (en) | 2005-04-13 |
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