JP2014122204A - 光酸発生化合物およびそれを含むフォトレジスト組成物、そのフォトレジストを含むコーティングされた物品、並びに物品を製造する方法 - Google Patents
光酸発生化合物およびそれを含むフォトレジスト組成物、そのフォトレジストを含むコーティングされた物品、並びに物品を製造する方法 Download PDFInfo
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- JP2014122204A JP2014122204A JP2013212445A JP2013212445A JP2014122204A JP 2014122204 A JP2014122204 A JP 2014122204A JP 2013212445 A JP2013212445 A JP 2013212445A JP 2013212445 A JP2013212445 A JP 2013212445A JP 2014122204 A JP2014122204 A JP 2014122204A
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- alkyl
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- sulfonate
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 31
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 52
- 239000000203 mixture Substances 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 25
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 24
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 150000001450 anions Chemical class 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 10
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims abstract description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 8
- 150000003457 sulfones Chemical class 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims abstract description 6
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 6
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 238000011161 development Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000005560 phenanthrenylene group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000001459 lithography Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 238000002835 absorbance Methods 0.000 abstract description 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 30
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 22
- 239000002904 solvent Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 0 CC=CC(N1CCCC1)=C* Chemical compound CC=CC(N1CCCC1)=C* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- -1 sulfonium cation Chemical class 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000002596 lactones Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PYTQULGOMFBQNV-UHFFFAOYSA-N 4,4,4-trifluoro-3-(trifluoromethyl)butane-1,3-diol Chemical compound OCCC(O)(C(F)(F)F)C(F)(F)F PYTQULGOMFBQNV-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 3
- QMBSJPZHUJCMJU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)propanoic acid Chemical class CCOCCOC(C)C(O)=O QMBSJPZHUJCMJU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 2
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- 238000000671 immersion lithography Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 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
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 1
- NNZZMYIWZFZLHU-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanol Chemical compound OC(F)(F)C(F)(F)F NNZZMYIWZFZLHU-UHFFFAOYSA-N 0.000 description 1
- QXJCOPITNGTALI-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)C(F)(F)F QXJCOPITNGTALI-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- JIXHYWCLUOGIMM-UHFFFAOYSA-N 2-(2-methoxyethoxy)propanoic acid Chemical compound COCCOC(C)C(O)=O JIXHYWCLUOGIMM-UHFFFAOYSA-N 0.000 description 1
- GWNOMIHBJSJJFX-UHFFFAOYSA-N 2-(adamantane-1-carbonyloxy)-1,1-difluoroethanesulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.C1C(C2)CC3CC2CC1(C(=O)OCC(F)(F)S(=O)(=O)[O-])C3 GWNOMIHBJSJJFX-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- SLEPTJJRHVICMA-UHFFFAOYSA-N OC(CC(C1)C2)(CC1C1)CC21C(OCCC(C(F)(F)S(O)(=O)=O)(F)F)=O Chemical compound OC(CC(C1)C2)(CC1C1)CC21C(OCCC(C(F)(F)S(O)(=O)=O)(F)F)=O SLEPTJJRHVICMA-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
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- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
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- 238000010537 deprotonation reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
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- 239000013020 final formulation Substances 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
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- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 239000002198 insoluble material Substances 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- DDMCDMDOHABRHD-UHFFFAOYSA-N methyl 2-hydroxybutanoate Chemical compound CCC(O)C(=O)OC DDMCDMDOHABRHD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- LLFNZCQAFAVOLK-UHFFFAOYSA-N tert-butyl 4-oxo-1h-pyridine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC(O)=CC=N1 LLFNZCQAFAVOLK-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WZCZNEGTXVXAAS-UHFFFAOYSA-N trifluoromethanol Chemical compound OC(F)(F)F WZCZNEGTXVXAAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
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Abstract
【解決手段】式(I)を有する化合物。
(aは、1〜10の整数;xは、1〜3の整数;X1は、フルオロアルコール、フッ素化エステル、又はフッ素化無水物;Yは、一重結合、C1−20アルキレン基、O、S、NR、エステル、カルボナート、スルホナート、スルホン、又はスルホンアミド;Arは、C5以上の単環式、多環式、若しくは縮合多環式シクロアルキルであるか、又はC5以上の単環式、多環式、若しくは縮合多環式アリール基;R1は、置換C5−40アリール、置換C5−40ヘテロアリール、C1−40アルキル、C3−40シクロアルキル;Z−は、カルボキシラート、スルファート、スルホナート、スルファマート又はスルホンイミドのアニオンであり、ここで、Yが一重結合である場合、Z−はスルホナートではない)
【選択図】なし
Description
該フォトレジスト組成物層を化学線にパターン露光する工程;ならびに
該パターンを、水性アルカリ性現像剤による処理によって現像してポジ型レリーフ像を形成するか、または有機溶剤現像剤による処理によって現像してネガ型レリーフ像を形成する工程を含む。
Claims (10)
- 式(I)を有する化合物:
X1はフルオロアルコール、フッ素化エステルまたはフッ素化無水物を含み、
Yは一重結合、C1−20アルキレン基、O、S、NR、エステル、カルボナート、スルホナート、スルホンまたはスルホンアミドであり、ここでRはHまたはC1−20アルキルであり、前記C1−20アルキレン基は、構造上炭素だけであるか、あるいはC1−20アルキレン基中の1以上の構造上の炭素原子は酸素、カルボニル、エステル、または前述の少なくとも1つを含む組合せによって置き換えられており、
Arは置換もしくは非置換のC5以上の単環式、多環式、もしくは縮合多環式シクロアルキルであるか、または置換もしくは非置換のC5以上の単環式、多環式、もしくは縮合多環式アリール基であり、ここで前記シクロアルキルまたはアリールは炭素環であるか、またはO、S、N、Fもしくは前述の少なくとも1つを含む組合せを含むヘテロ原子を含み、
各々のR1は独立に、置換C5−40アリール、置換C5−40ヘテロアリール、C1−40アルキル、C3−40シクロアルキルであり、ここでxが1である場合、2つの基R1は、互いに結合していないかまたは互いに結合してC4−40環構造を形成しており、並びに
Z−はカルボキシラート、スルファート、スルホナート、スルファマートまたはスルホンイミドのアニオンであり、ここでYが一重結合である場合、Z−はスルホナートではない)。 - aが1〜4の整数であり、xが1であり、X1が1,1,1,3,3,3−ヘキサフルオロイソプロパノール含有基またはC1−20パーフルオロアルコールのエステルであり、Yが−O−、−S−、NR−、−O−C(=O)−、−C(=O)−O−、−O−C(=O)−O−、−OCH2−(C=O)O−、−OCH2C(=O)−、−SO2−、−O−SO2−、または前述の基の少なくとも1つを含む組合せであり、ここで、RがHまたはC1−6アルキルである、請求項1に記載の化合物。
- Arが置換もしくは非置換フェニレン、ナフチレン、アントラセニレン、フェナントレニレン、キノリニレン、ジベンゾチオフェニレン、チオキサントン、チオオキサアントラセニレン、または前述の少なくとも1つを含む組合せである、請求項1または2に記載の化合物。
- R1が独立に、置換C5−20アリールまたはC1−20アルキルであり、ここでxが1である場合、2つの基R1が互いに結合していないかまたは互いに結合してC4−20環構造を形成している、請求項1〜3のいずれか一項に記載の化合物。
- 前記化合物が、式(Ia)、(Ib)、(Ic)、(Id)、または(Ie)を有する、請求項1に記載の化合物:
X1はフルオロアルコールを含有するC3−10有機基またはC1−20パーフルオロアルコールのエステルであり、Yは−O−、−S−、NR−、−O−C(=O)−、−C(=O)−O−、−O−C(=O)−O−、−OCH2−(C=O)O−、−OCH2C(=O)−、−SO2−、−O−SO2−、または前述の基の少なくとも1つを含む組合せであり、およびRはHまたはC1−6アルキルであり、
Ar2は置換もしくは非置換フェニレン、ナフチレン、アントラセニレン、フェナントレニレン、キノリニレン、ジベンゾチオフェニレン、チオキサントン、チオキサンテニレン、または前述の少なくとも1つを含む組合せであり、
各々のR2およびR3は、独立に、Arと同一でない置換C5−20アリール、またはC1−20アルキルであり、およびLは置換もしくは非置換C2−20アルキレンであり、並びに
Z−は、スルファート、スルホナート、またはスルホンイミドのアニオンである)。 - 式(IIIa)〜(IIIg)を含む、請求項1に記載の化合物:
X2は、1,1,1,3,3,3−ヘキサフルオロイソプロパノール含有基を含有するC3−10有機基またはC1−20パーフルオロアルコールのエステルであり、
Yは、−O−、−S−、NR−、−O−C(=O)−、−C(=O)−O−、−O−C(=O)−O−、−OCH2−(C=O)O−、−OCH2C(=O)−、−SO2−、−O−SO2−、または前述の基の少なくとも1つを含む組合せであり、およびRはHまたはC1−6アルキルであり、
各々のR2およびR3は、独立に、Arと同一でない置換C5−20アリール、またはC1−20アルキルであり、およびLは置換もしくは非置換C2−20アルキレンであり、並びに
Z−は、カルボキシラート、スルファート、スルホナート、スルファマート、またはスルホンイミドのアニオンである)。 - Z−が、式(II)を有する、請求項1に記載の化合物:
Aは、O、S、N、F、または前述の少なくとも1つを含む組合せを場合によって含む、置換もしくは非置換の、単環式、多環式、もしくは縮合多環式のC3以上の脂環式基、または、重合可能な二重もしくは三重結合を含有するC3以上の脂肪族もしくは脂環式基であり、
R4は、H、一重結合、または置換もしくは非置換C1−30アルキル基であり、ここで、R4が一重結合である場合、R4はAの炭素原子と共有結合しており、
各々のR5は、独立に、H、F、またはC1−4フルオロアルキルであり、ここで少なくとも1つのR5は水素ではなく、
Lは、−O−、−S−、−C(=O)−、カルボナート、カルボキシラート、スルホナート、スルファート、またはスルホンアミド基を含む連結基であり、並びに
qは0〜10の整数であり、mは0以上の整数であり、nは1以上の整数である)。 - 請求項1〜7のいずれか一項に記載の化合物および酸不安定保護基を有するポリマーを含む、フォトレジスト。
- (a)その表面上でパターン形成される1以上の層を有する基体;および(b)前記パターン形成される1以上の層の上の、請求項8に記載のフォトレジスト組成物の層を含むコーティングされた基体。
- レリーフ像を製造する方法であって、
酸脱保護性基を有するポリマー、および
式(I)を有する化合物
X1はフルオロアルコール、フッ素化エステルまたはフッ素化無水物を含み、
Yは一重結合、C1−20アルキレン基、O、S、NR、エステル、カルボナート、スルホナート、スルホンまたはスルホンアミドであり、ここでRはHまたはC1−20アルキルであり、前記C1−20アルキレン基は、構造上炭素だけであるか、あるいはC1−20アルキレン基中の1以上の構造上の炭素原子は酸素、カルボニル、エステル、または前述の少なくとも1つを含む組合せによって置き換えられており、
Arは置換もしくは非置換のC5以上の単環式、多環式、もしくは縮合多環式シクロアルキルであるか、または置換もしくは非置換のC5以上の単環式、多環式、もしくは縮合多環式アリール基であり、ここで前記シクロアルキルまたはアリールは炭素環であるか、またはO、S、N、Fもしくは前述の少なくとも1つを含む組合せを含むヘテロ原子を含み、
各々のR1は独立に、置換C5−40アリール、置換C5−40ヘテロアリール、C1−40アルキル、C3−40シクロアルキルであり、ここでxが1である場合、2つの基R1は、互いに結合していないかまたは互いに結合してC4−40環構造を形成しており、並びに
Z−はカルボキシラート、スルファート、スルホナート、スルファマートまたはスルホンイミドのアニオンであり、ここでYが一重結合である場合、Z−はスルホナートではない)
を含むフォトレジスト層で基体をコーティングする工程、
前記フォトレジスト組成物層を化学線にパターン露光する工程、ならびに
前記パターンを、水性アルカリ性現像剤による処理によって現像してポジ型レリーフ像を形成するか、または有機溶剤現像剤による処理によって現像してネガ型レリーフ像を形成する工程を含む方法。
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