JP3841406B2 - レジスト組成物 - Google Patents
レジスト組成物 Download PDFInfo
- Publication number
- JP3841406B2 JP3841406B2 JP2002112372A JP2002112372A JP3841406B2 JP 3841406 B2 JP3841406 B2 JP 3841406B2 JP 2002112372 A JP2002112372 A JP 2002112372A JP 2002112372 A JP2002112372 A JP 2002112372A JP 3841406 B2 JP3841406 B2 JP 3841406B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- resin
- resist composition
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims description 90
- 239000011347 resin Substances 0.000 claims description 147
- 125000000217 alkyl group Chemical group 0.000 claims description 146
- 229920005989 resin Polymers 0.000 claims description 146
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000005843 halogen group Chemical group 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 125000001153 fluoro group Chemical group F* 0.000 claims description 43
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 150000001450 anions Chemical class 0.000 claims description 21
- 230000005855 radiation Effects 0.000 claims description 19
- 238000004090 dissolution Methods 0.000 claims description 18
- 125000002950 monocyclic group Chemical group 0.000 claims description 17
- 239000010703 silicon Substances 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 12
- 230000000269 nucleophilic effect Effects 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 150000007514 bases Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 8
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 claims description 7
- 238000011161 development Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 5
- 230000003321 amplification Effects 0.000 claims description 3
- 238000003199 nucleic acid amplification method Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- -1 sulfonate anion Chemical class 0.000 description 136
- 125000004432 carbon atom Chemical group C* 0.000 description 82
- 125000001424 substituent group Chemical group 0.000 description 79
- 125000000753 cycloalkyl group Chemical group 0.000 description 39
- 239000000243 solution Substances 0.000 description 36
- 229920001577 copolymer Polymers 0.000 description 33
- 125000002723 alicyclic group Chemical group 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000004215 Carbon black (E152) Substances 0.000 description 21
- 229930195733 hydrocarbon Natural products 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
- 230000035945 sensitivity Effects 0.000 description 17
- 125000002252 acyl group Chemical group 0.000 description 16
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 125000000547 substituted alkyl group Chemical group 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 229910052740 iodine Inorganic materials 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 150000002989 phenols Chemical class 0.000 description 13
- 125000003367 polycyclic group Chemical group 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 11
- 125000004423 acyloxy group Chemical group 0.000 description 11
- 125000000732 arylene group Chemical group 0.000 description 11
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- 125000004185 ester group Chemical group 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 229920002120 photoresistant polymer Polymers 0.000 description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 125000004450 alkenylene group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 8
- 0 CCCC1CC(CC2(C3C2)C3=CC)*C1 Chemical compound CCCC1CC(CC2(C3C2)C3=CC)*C1 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 7
- 229920006362 Teflon® Polymers 0.000 description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
- 125000002993 cycloalkylene group Chemical group 0.000 description 7
- 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 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
- 125000005647 linker group Chemical group 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 125000004849 alkoxymethyl group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000001312 dry etching Methods 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 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 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 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 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 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 5
- 125000000962 organic group Chemical group 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004036 acetal group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 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 4
- 230000000694 effects Effects 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000011156 evaluation Methods 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
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 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 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- AIBKTSSWLZGMLQ-UHFFFAOYSA-N tert-butyl 2-(4-ethenylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=C(C=C)C=C1 AIBKTSSWLZGMLQ-UHFFFAOYSA-N 0.000 description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 230000004304 visual acuity Effects 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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 150000001334 alicyclic compounds Chemical class 0.000 description 3
- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000005382 boronyl group Chemical group 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
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- PTVAFUMXLZLZEZ-UHFFFAOYSA-N tert-butyl 2-(3-ethenylphenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=CC(C=C)=C1 PTVAFUMXLZLZEZ-UHFFFAOYSA-N 0.000 description 1
- KHEOWODWWPOGTJ-UHFFFAOYSA-N tert-butyl 2-(4-ethenyl-2-methylphenoxy)acetate Chemical compound CC1=CC(C=C)=CC=C1OCC(=O)OC(C)(C)C KHEOWODWWPOGTJ-UHFFFAOYSA-N 0.000 description 1
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- HPBNICVODIHXKB-UHFFFAOYSA-N tert-butyl 4-ethenylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C=C)C=C1 HPBNICVODIHXKB-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
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- XZZGCKRBJSPNEF-UHFFFAOYSA-M triphenylsulfanium;acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 XZZGCKRBJSPNEF-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20110025105A (ko) * | 2009-09-01 | 2011-03-09 | 후지필름 가부시키가이샤 | 감활성광선성 또는 감방사선성 수지 조성물 및 그것을 사용한 패턴형성방법 |
| KR20140000129A (ko) | 2010-12-24 | 2014-01-02 | 후지필름 가부시키가이샤 | 감활성광선성 또는 감방사선성 수지 조성물, 이 조성물을 사용한 감활성광선성 또는 감방사선성 막 및 패턴형성방법 |
| US9316911B2 (en) | 2011-06-30 | 2016-04-19 | Fujifilm Corporation | Actinic-ray- or radiation-sensitive resin composition, actinic-ray- or radiation-sensitive film therefrom and method of forming pattern using the composition |
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| US7217492B2 (en) * | 2002-12-25 | 2007-05-15 | Jsr Corporation | Onium salt compound and radiation-sensitive resin composition |
| JP4810862B2 (ja) * | 2005-04-11 | 2011-11-09 | Ｊｓｒ株式会社 | オニウム塩、それを用いた感放射線性酸発生剤及びポジ型感放射線性樹脂組成物 |
| JP4770244B2 (ja) * | 2005-04-11 | 2011-09-14 | Ｊｓｒ株式会社 | オニウム塩、それを用いた感放射線性酸発生剤及びポジ型感放射線性樹脂組成物 |
| JP2009029848A (ja) * | 2007-07-24 | 2009-02-12 | Mitsubishi Rayon Co Ltd | 重合体及びその製造方法、レジスト組成物及びパターンが形成された基板の製造方法 |
| JP5557625B2 (ja) * | 2010-06-30 | 2014-07-23 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物並びに該組成物を用いたレジスト膜及びパターン形成方法 |
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| JP5277304B2 (ja) * | 2010-12-24 | 2013-08-28 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、並びに、この組成物を用いた感活性光線性又は感放射線性膜及びパターン形成方法 |
| WO2012098828A1 (ja) * | 2011-01-21 | 2012-07-26 | 三菱瓦斯化学株式会社 | 低分子化合物、感放射線性組成物、およびレジストパターン形成方法 |
| JP5746907B2 (ja) * | 2011-04-28 | 2015-07-08 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物並びに該組成物を用いたレジスト膜及びパターン形成方法 |
| JP6539760B2 (ja) * | 2012-12-26 | 2019-07-03 | 東京応化工業株式会社 | 化合物 |
| JP6088827B2 (ja) * | 2013-01-10 | 2017-03-01 | 富士フイルム株式会社 | ネガ型レジスト組成物、それを用いたレジスト膜及びパターン形成方法、並びにレジスト膜を備えたマスクブランクス |
| JP6313604B2 (ja) * | 2014-02-05 | 2018-04-18 | 富士フイルム株式会社 | 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、感活性光線性又は感放射線性膜を備えたマスクブランクス、パターン形成方法、及び電子デバイスの製造方法 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110025105A (ko) * | 2009-09-01 | 2011-03-09 | 후지필름 가부시키가이샤 | 감활성광선성 또는 감방사선성 수지 조성물 및 그것을 사용한 패턴형성방법 |
| KR101727105B1 (ko) * | 2009-09-01 | 2017-04-14 | 후지필름 가부시키가이샤 | 감활성광선성 또는 감방사선성 수지 조성물 및 그것을 사용한 패턴형성방법 |
| KR20140000129A (ko) | 2010-12-24 | 2014-01-02 | 후지필름 가부시키가이샤 | 감활성광선성 또는 감방사선성 수지 조성물, 이 조성물을 사용한 감활성광선성 또는 감방사선성 막 및 패턴형성방법 |
| US9081277B2 (en) | 2010-12-24 | 2015-07-14 | Fujifilm Corporation | Actinic-ray- or radiation-sensitive resin composition, actinic-ray- or radiation-sensitive film therefrom and method of forming pattern using the composition |
| US9316911B2 (en) | 2011-06-30 | 2016-04-19 | Fujifilm Corporation | Actinic-ray- or radiation-sensitive resin composition, actinic-ray- or radiation-sensitive film therefrom and method of forming pattern using the composition |
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| Publication number | Publication date |
|---|---|
| JP2003307839A (ja) | 2003-10-31 |
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