JP7441930B2 - フォトレジスト組成物及びパターン形成方法 - Google Patents
フォトレジスト組成物及びパターン形成方法 Download PDFInfo
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- JP7441930B2 JP7441930B2 JP2022204307A JP2022204307A JP7441930B2 JP 7441930 B2 JP7441930 B2 JP 7441930B2 JP 2022204307 A JP2022204307 A JP 2022204307A JP 2022204307 A JP2022204307 A JP 2022204307A JP 7441930 B2 JP7441930 B2 JP 7441930B2
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- substituted
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- alkyl
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- 229920002120 photoresistant polymer Polymers 0.000 title claims description 134
- 239000000203 mixture Substances 0.000 title claims description 108
- 238000000034 method Methods 0.000 title claims description 23
- 229920000642 polymer Polymers 0.000 claims description 159
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 125000005647 linker group Chemical group 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 230000005855 radiation Effects 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 9
- 125000000686 lactone group Chemical group 0.000 claims description 9
- 150000002596 lactones Chemical class 0.000 claims description 7
- 230000003213 activating effect Effects 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 5
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 5
- 150000008027 tertiary esters Chemical group 0.000 claims description 5
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical group C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical group C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 description 20
- -1 -CF 3 Chemical compound 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 125000005842 heteroatom Chemical group 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- 235000012431 wafers Nutrition 0.000 description 18
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 16
- 238000011161 development Methods 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000005907 alkyl ester group Chemical group 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000002993 cycloalkylene group Chemical group 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000000732 arylene group Chemical group 0.000 description 10
- 125000003367 polycyclic group Chemical group 0.000 description 10
- 101000585551 Equus caballus Pregnancy-associated glycoprotein Proteins 0.000 description 9
- 101001124867 Homo sapiens Peroxiredoxin-1 Proteins 0.000 description 9
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000005549 heteroarylene group Chemical group 0.000 description 8
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 238000000059 patterning Methods 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000002318 adhesion promoter Substances 0.000 description 4
- 230000003667 anti-reflective effect Effects 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002891 organic anions Chemical class 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000004513 sizing Methods 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 229910052581 Si3N4 Inorganic materials 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
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000007860 aryl ester derivatives Chemical class 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000609 electron-beam lithography Methods 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002892 organic cations Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 description 2
- 125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000010504 bond cleavage reaction Methods 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000008028 secondary esters Chemical group 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound 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
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical class C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- COBURCRUNDBUGQ-UHFFFAOYSA-N tert-butyl 2-ethylimidazole-1-carboxylate Chemical compound CCC1=NC=CN1C(=O)OC(C)(C)C COBURCRUNDBUGQ-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 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
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
- C08F212/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1809—C9-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2012—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
のモノマーから誘導され得る。
(式中、Rbは、式(1)において定義された通りである)
を含む。
の1つ以上によって表されるモノマーから誘導され得る。
(式中、Rdは、式(2a)に関して定義された通りである)
の1つ以上を含む。
(式中、Rdは、式(2b)において定義された通りであり、R’及びR’’は、それぞれ独立して、置換若しくは無置換C1~20アルキル、置換若しくは無置換C3~20シクロアルキル、置換若しくは無置換C3~20ヘテロシクロアルキル、置換若しくは無置換C2~20アルケニル、置換若しくは無置換C3~20シクロアルケニル、置換若しくは無置換C3~20ヘテロシクロアルケニル、置換若しくは無置換C6~20アリール又は置換若しくは無置換C3~20ヘテロアリールである)
の1つ以上を含む。
(式中、Rdは、式(2c)に関して定義された通りである)
の1つ以上を含む。
(式中、Rdは、式(2d)に関して定義された通りである)
の1つ以上を含む。
(式中、Rdは、式(2e)に関して定義された通りである)
の1つ以上を含む。
(式中、Rdは、式(2a)に関して定義された通りである)
の1つ以上を有する1種以上のモノマーから誘導され得る。
(式中、Rdは、式(2a)に関して定義された通りである)
の1つ以上のモノマーであり得る。
のフルオロアルコール基を含むモノマーから誘導され得る。
(式中、Raは、式(3)について定義された通りである)
の1つ以上を含み得る。
(式中、a、b及びcは、それぞれ各繰り返し単位の相対的なモル量を示す)
の1つ以上を含む。
の1種以上のモノマーから誘導され得る。
(式中、mは、1又は2であり;各R1aは、独立して、水素又は無置換C1~2アルキルであるが、少なくとも1つのR1aが無置換C1~2アルキル、典型的には少なくとも1つのR1aがメチルである(例えば、mが2である場合、炭素-炭素二重結合に隣接する最初のR1a基は、メチル基であり得、2番目のR1a基は、水素であり得、R1bは、無置換C1~2アルキル、典型的にはメチルである)ことを条件とし;R1bは、無置換C1~2アルキル、典型的にはメチルである)
のモノマーを含む。
(式中、Rfは、式(4a)のRgに関して定義された通りである)
の1つ以上を含み得る。
の1種以上のモノマーから誘導され得る。
(式中、Rjは、式(5b)に関して定義された通りである)
の1つ以上を含む。
(式中、a、b及びcは、それぞれの各繰り返し単位の相対的なモル量を示す)
の1つ以上を含む。
であり得る。
の1つ以上を含み得る。
の1つ以上を含み得る。
の1つ以上を含む。
の1つ以上を含む。
の1種以上のモノマーに由来する繰り返し単位を任意選択的に更に含み得る。
(式中、G+は、本明細書で定義された有機カチオンである)
の1つ以上を含み得る。
(式中、Xeは、C2アルケニル及び(メタ)アクリルから選択される重合性基であり;L13は、二価連結基であり;Rnは、置換又は無置換C1~20フルオロアルキルであるが、式(8)中のカルボニル(-C(O)-)に結合している炭素原子は、少なくとも1つのフッ素原子で置換されていることを条件とする)
の1種以上のモノマーに由来する繰り返し単位を含むポリマーであり得る。例示的な式(8)のモノマーは、以下:
の1つ以上を含み得る。
(式中、Xf及びRpは、それぞれ式(8)でXe及びRnについて定義された通りであり;L14は、置換若しくは無置換C1~20アルキレン、置換若しくは無置換C3~20シクロアルキレン、-C(O)-又は-C(O)O-の1つ以上を含む多価連結基であり;n3は、2以上の整数、例えば2又は3であり得る)
の1種以上のモノマーに由来する繰り返し単位を含み得る。式(9)の例示的なモノマーは、以下:
の1つ以上を含み得る。
(式中、Xg及びRqは、式(10)でそれぞれXe及びRnについて定義された通りであり;L15は、二価連結基であり;L16は、置換又は無置換C1~20フルオロアルキレンであり、式(10)中のカルボニル(-C(O)-)に結合している炭素原子は、少なくとも1個のフッ素原子で置換されている)
の1種以上のモノマーに由来する繰り返し単位を含み得る。例示的な式(10)のモノマーは、以下:
の1つ以上を含み得る。
の1つ以上を含む。
この実施例は、ポリマーP1-A~P1-G、P2-A~P2-P2-H及びP3-A~P3-Bの一般的な合成を記述する。以下のモノマーは、それぞれの比較のポリマー及び本発明のポリマーを調製するために使用した1つ以上の構造を表す。
実施例2
表1からのポリマーを使用するフォトレジスト組成物は、表2に示される成分を混ぜ合わせることによって調製した。ここで、量は、組成物の総重量100重量%に基づく重量パーセント(重量%)で表される。フォトレジスト組成物の総固形分は、1.55重量%であった。フォトレジスト組成物は、重量比1:1のプロピレングリコールモノメチルエーテルアセテート(PGMEA)とメチル-2-ヒドロキシイソブチレートとの溶媒混合物中で調製した。
フォトレジスト組成物を、明視野マスクパターンを使用してKrF露光下でライン/スペースパターニングについて評価した。TEL Clean Track ACT 8ウェハートラック上で、BARCスタックでオーバーコートした200mmのシリコンウェハー(厚さ80nmのAR(商標)40A反射防止材の上に厚さ60nmのAR(商標)3反射防止材を積層したもの、[DuPont Electronics&Industrial])をそれぞれ各フォトレジスト組成物でスピンコートし、110℃で60秒間ソフトベークし、厚みが約40nmのフォトレジスト層を得た。ウェハーを、120nmのライン/スペース(L/S)パターンを有するマスクを使用してCANON FPA-5000 ES4スキャナー(NA=0.8、アウターシグマ=0.85、インナーシグマ=0.57)で248nmの放射でそれぞれ露光した。ウェハーを100℃で60秒間露光後ベークし、MF(商標)-CD26 TMAH現像液(DuPont Electronics&Imaging)で60秒間現像し、脱イオン水でリンスし、乾燥させた。形成されたL/Sパターンの限界寸法(CD)測定は、HITACHI S-9380 CD SEMで行った。サイジングエネルギー(Esize)及びラインの線幅粗さ(LWR)は、CD測定に基づいて決定した。サイジングエネルギーは、目標の120nmのL/Sパターンが解像された照射エネルギーである。
表4のフォトレジスト組成物を、上述したKrF露光下で暗視野マスクパターンを使用してライン/スペース(L/S)パターニングについて評価した。サイジングエネルギー(Esize)及びスペースの線幅粗さ(LWR)は、CD測定に基づいて決定した。サイジングエネルギーは、目標の120nmのL/Sパターンが解像された照射エネルギーから決定した。結果を表4に示す。
Claims (11)
- 第1のポリマーであって、
ヒドロキシアリール基を含む第1の繰り返し単位と、
第1の酸不安定基を含む第2の繰り返し単位と、
第1の塩基可溶性基を含む第3の繰り返し単位であって、前記第1の塩基可溶性基は、12以下のpKaを有し、前記第1の塩基可溶性基は、ヒドロキシアリール基を含まず、前記第1のポリマーの前記第3の繰り返し単位は、前記第1のポリマー中の繰り返し単位の合計を基準として1~25モル%の量で存在する、第3の繰り返し単位と
を含み、
前記第1のポリマーの前記第1の繰り返し単位、前記第2の繰り返し単位及び前記第3の繰り返し単位は、互いに構造的に異なり、
第1のポリマーは、ラクトン基を含まない、第1のポリマーと、
第2のポリマーであって、
第2の酸不安定基を含む第1の繰り返し単位と、
ラクトン基を含む第2の繰り返し単位であって、前記第2のポリマー中の前記第2の繰り返し単位は、前記第2のポリマー中の繰り返し単位の総モル数を基準として15~65モル%の量で存在する、第2の繰り返し単位と、
12以下のpKaを有する第2の塩基可溶性基を含む第3の繰り返し単位と
を含み、
前記第2のポリマーの前記第1の繰り返し単位、前記第2の繰り返し単位及び前記第3の繰り返し単位は、互いに構造的に異なる、第2のポリマーと、
溶媒と
を含むフォトレジスト組成物であって、前記第1のポリマーと前記第2のポリマーとは、互いに異なる、フォトレジスト組成物。 - 光酸発生剤を更に含む、請求項1に記載のフォトレジスト組成物。
- 前記第1の塩基可溶性基は、フルオロアルコール基、カルボン酸基、スルホンイミド基、スルホンアミド基又はカルボキシイミド基を含む、請求項1に記載のフォトレジスト組成物。
- 前記第1のポリマーの前記第3の繰り返し単位は、式(3):
Raは、水素、ハロゲン又は置換若しくは無置換C1~10アルキルであり、
L1は、-O-、-C(O)-、又は-C(O)O-、又は-C(O)NR’-であり、
R’は、水素又は置換若しくは無置換C1~5アルキル基であり、
a1は、0又は1であり、
L2は、単結合又は多価連結基であり、
各R1は、置換又は無置換C1~12パーフルオロアルキル基であり、
各R2は、置換若しくは無置換C1~12アルキル、置換若しくは無置換C3~12シクロアルキル又は置換若しくは無置換C1~12ヘテロシクロアルキルであり、R2は、1つ以上のフッ素原子を任意選択的に含み、及び
n1は、1~5の整数である)
のモノマーから誘導される、請求項3に記載のフォトレジスト組成物。 - 前記第1ポリマーの前記第1の繰り返し単位は、式(1):
Rbは、水素、ハロゲン又は置換若しくは無置換C1~10アルキルであり、
Rcは、水素、L4と共に環を形成する-C(O)-又はAr1と共に環を形成する単結合であり、
L3は、-O-、-C(O)-又は-C(O)O-であり、a2は、0又は1であり、
L4は、単結合又は1つ以上の二価連結基であり、及び
Ar1は、それぞれ任意選択的に置換若しくは無置換C1~30アルキル、置換若しくは無置換C1~30ヘテロアルキル、置換若しくは無置換C3~30シクロアルキル、置換若しくは無置換C1~30ヘテロシクロアルキル、置換若しくは無置換C2~30アルケニル、置換若しくは無置換C2~30アルキニル、置換若しくは無置換C6~30アリール、置換若しくは無置換C7~30アリールアルキル、置換若しくは無置換C7~30アルキルアリール、置換若しくは無置換C3~30ヘテロアリール又は置換若しくは無置換C4~30ヘテロアリールアルキル、-OR1c又は-NR1dR1eの1つ以上で更に置換されている、ヒドロキシ置換C6~60アリール基、ヒドロキシ置換C5~60ヘテロアリール基又はそれらの組み合わせを含み、R1c~R1eは、それぞれ独立して、置換若しくは無置換C1~30アルキル、置換若しくは無置換C3~30シクロアルキル、置換若しくは無置換C2~30ヘテロシクロアルキル、置換若しくは無置換C6~30アリール、置換若しくは無置換C7~30アリールアルキル、置換若しくは無置換C3~30ヘテロアリール又は置換若しくは無置換C4~30ヘテロアリールアルキルである)
のモノマーから誘導される、請求項1に記載のフォトレジスト組成物。 - 前記第1の酸不安定基及び前記第2の酸不安定基は、それぞれ独立して、三級エステル基から選択される、請求項1に記載のフォトレジスト組成物。
- 前記第2ポリマーの前記第2の繰り返し単位は、式(4a)又は(4b):
Rgは、水素、ハロゲン又は置換若しくは無置換C1~10アルキルであり、
L8は、単結合又は1つ以上の二価連結基であり、
R18は、置換又は無置換C4~20ラクトン含有基であり、
各R21は、独立して、ハロゲン、置換若しくは無置換C1~30アルキル、置換若しくは無置換C1~30ヘテロアルキル、置換若しくは無置換C3~30シクロアルキル、置換若しくは無置換C3~20ヘテロシクロアルキル、置換若しくは無置換C2~20アルケニル、置換若しくは無置換C3~20シクロアルケニル、置換若しくは無置換C3~20ヘテロシクロアルケニル、C6~30アリール、置換若しくは無置換C7~30アリールアルキル、置換若しくは無置換C7~30アルキルアリール、置換若しくは無置換C3~30ヘテロアリール、置換若しくは無置換C4~30ヘテロアリールアルキル又は置換若しくは無置換C4~30アルキルヘテロアリールであり、各R21は、任意選択的に、その構造の一部として二価連結基を更に含み、
R22及びR23は、それぞれ独立して、水素、ハロゲン、置換若しくは無置換C1~30アルキル、置換若しくは無置換C1~30ヘテロアルキル、置換若しくは無置換C3~30シクロアルキル、置換若しくは無置換C3~20ヘテロシクロアルキル、C6~30アリール、置換若しくは無置換C7~30アリールアルキル、置換若しくは無置換C7~30アルキルアリール、置換若しくは無置換C3~30ヘテロアリール、置換若しくは無置換C4~30ヘテロアリールアルキル又は置換若しくは無置換C4~30アルキルヘテロアリールであり、R22及びR23の各々は、独立して、任意選択的に、その構造の一部として二価連結基を更に含み、
m1は、1又は2であり、及び
n1は、1~6の整数である)
のモノマーから誘導される、請求項1に記載のフォトレジスト組成物。 - 前記第2のポリマーの前記第3の繰り返し単位は、式(5a)、(5b)、(5c)又は(5d):
Rh、Rj、Rk及びRlは、それぞれ独立して、水素、ハロゲン又は置換若しくは無置換C1~10アルキルであり、
L11、L12及びL13は、それぞれ独立して、単結合又は多価連結基であり、
Ar2は、置換若しくは無置換C6~30アリール又は置換若しくは無置換C3~30ヘテロアリールであり、
R24 は、置換又は無置換C1~20アルキルであり、
R25は、水素又はメチルであり、
a7及びa8は、それぞれ独立して、1~5の整数であり、
a9は、0又は1であり、及び
a10は、1~12の整数である)
のモノマーから誘導される、請求項1に記載のフォトレジスト組成物。 - 前記第1のポリマー対前記第2のポリマーの重量比は、1:4~4:1である、請求項1に記載のフォトレジスト組成物。
- 前記第2ポリマーの前記第3の繰り返し単位は、式(1)又は式(3):
R b は、水素、ハロゲン又は置換若しくは無置換C 1~10 アルキルであり、
R c は、水素、L 4 と共に環を形成する-C(O)-又はAr 1 と共に環を形成する単結合であり、
L 3 は、-O-、-C(O)-又は-C(O)O-であり、a2は、0又は1であり、
L 4 は、単結合又は1つ以上の二価連結基であり、及び
Ar 1 は、それぞれ任意選択的に置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 1~30 ヘテロアルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 1~30 ヘテロシクロアルキル、置換若しくは無置換C 2~30 アルケニル、置換若しくは無置換C 2~30 アルキニル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 7~30 アルキルアリール、置換若しくは無置換C 3~30 ヘテロアリール又は置換若しくは無置換C 4~30 ヘテロアリールアルキル、-OR 1c 又は-NR 1d R 1e の1つ以上で更に置換されている、ヒドロキシ置換C 6~60 アリール基、ヒドロキシ置換C 5~60 ヘテロアリール基又はそれらの組み合わせを含み、R 1c ~R 1e は、それぞれ独立して、置換若しくは無置換C 1~30 アルキル、置換若しくは無置換C 3~30 シクロアルキル、置換若しくは無置換C 2~30 ヘテロシクロアルキル、置換若しくは無置換C 6~30 アリール、置換若しくは無置換C 7~30 アリールアルキル、置換若しくは無置換C 3~30 ヘテロアリール又は置換若しくは無置換C 4~30 ヘテロアリールアルキルである)
R a は、水素、ハロゲン又は置換若しくは無置換C 1~10 アルキルであり、
L 1 は、-O-、-C(O)-、又は-C(O)O-、又は-C(O)NR ’ -であり、
R ’ は、水素又は置換若しくは無置換C 1~5 アルキル基であり、
a1は、0又は1であり、
L 2 は、単結合又は多価連結基であり、
各R 1 は、置換又は無置換C 1~12 パーフルオロアルキル基であり、
各R 2 は、置換若しくは無置換C 1~12 アルキル、置換若しくは無置換C 3~12 シクロアルキル又は置換若しくは無置換C 1~12 ヘテロシクロアルキルであり、R 2 は、1つ以上のフッ素原子を任意選択的に含み、及び
n1は、1~5の整数である)
のモノマーから誘導される、請求項1に記載のフォトレジスト組成物。 - パターンを形成する方法であって、
(a)請求項1~10のいずれか一項に記載のフォトレジスト組成物から基板上にフォトレジスト層を形成することと、
(b)前記フォトレジスト層を活性化放射にパターン様露光することと、
(c)前記露光されたフォトレジスト層を現像してレジストレリーフ像を提供することとを含む方法。
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JP2010138383A (ja) | 2008-11-14 | 2010-06-24 | Sumitomo Chemical Co Ltd | 重合体及びフォトレジスト組成物 |
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WO2016035497A1 (ja) | 2014-09-02 | 2016-03-10 | 富士フイルム株式会社 | パターン形成方法、電子デバイスの製造方法及び電子デバイス |
JP2017214480A (ja) | 2016-05-31 | 2017-12-07 | 信越化学工業株式会社 | ポリマー、ポジ型レジスト材料、及びパターン形成方法 |
WO2018070327A1 (ja) | 2016-10-13 | 2018-04-19 | Jsr株式会社 | 感放射線性樹脂組成物及びレジストパターン形成方法 |
WO2020066342A1 (ja) | 2018-09-28 | 2020-04-02 | 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、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
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JP2015143819A (ja) | 2013-12-26 | 2015-08-06 | 信越化学工業株式会社 | レジスト組成物及びパターン形成方法 |
WO2016035497A1 (ja) | 2014-09-02 | 2016-03-10 | 富士フイルム株式会社 | パターン形成方法、電子デバイスの製造方法及び電子デバイス |
JP2017214480A (ja) | 2016-05-31 | 2017-12-07 | 信越化学工業株式会社 | ポリマー、ポジ型レジスト材料、及びパターン形成方法 |
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