CN112011008A - 抗蚀剂组合物、其制造方法及包含其的制品 - Google Patents
抗蚀剂组合物、其制造方法及包含其的制品 Download PDFInfo
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- CN112011008A CN112011008A CN202010418705.0A CN202010418705A CN112011008A CN 112011008 A CN112011008 A CN 112011008A CN 202010418705 A CN202010418705 A CN 202010418705A CN 112011008 A CN112011008 A CN 112011008A
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- 239000000203 mixture Substances 0.000 title claims description 62
- 238000004519 manufacturing process Methods 0.000 title description 7
- -1 C2‐C6Alkanoyl Chemical group 0.000 claims abstract description 75
- 229920000642 polymer Polymers 0.000 claims abstract description 70
- 239000002253 acid Substances 0.000 claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 28
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 238000006467 substitution reaction Methods 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000004185 ester group Chemical group 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000000815 N-oxide group Chemical group 0.000 claims abstract description 7
- 125000003368 amide group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 125000005587 carbonate group Chemical group 0.000 claims abstract description 7
- 125000005518 carboxamido group Chemical group 0.000 claims abstract description 7
- 125000001033 ether group Chemical group 0.000 claims abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 7
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract description 7
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 7
- 125000001174 sulfone group Chemical group 0.000 claims abstract description 7
- 125000003375 sulfoxide group Chemical group 0.000 claims abstract description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 229920002120 photoresistant polymer Polymers 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 150000008053 sultones Chemical group 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000004036 acetal group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000686 lactone group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- 235000012431 wafers Nutrition 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 150000003951 lactams Chemical class 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 239000012527 feed solution Substances 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 150000001721 carbon Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
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- 239000000460 chlorine Substances 0.000 description 3
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
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- 239000003999 initiator Substances 0.000 description 3
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- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 3
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- 125000004076 pyridyl group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
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- 125000001544 thienyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 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
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- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
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- 230000007423 decrease Effects 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 125000004193 piperazinyl group Chemical group 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 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 compound 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
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
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- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
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- DCUJJWWUNKIJPH-UHFFFAOYSA-N nitrapyrin Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=N1 DCUJJWWUNKIJPH-UHFFFAOYSA-N 0.000 description 1
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- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YBNLWIZAWPBUKQ-UHFFFAOYSA-N trichloro(trichloromethylsulfonyl)methane Chemical compound ClC(Cl)(Cl)S(=O)(=O)C(Cl)(Cl)Cl YBNLWIZAWPBUKQ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
-
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- 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
- C08F226/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
-
- 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
- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/38—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an acetal or ketal radical
-
- 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
- C08F220/08—Anhydrides
-
- 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
-
- 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
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
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Abstract
本文公开了包含第一重复单元和第二重复单元的聚合物,其中所述第一重复单元含有酸不稳定基团,并且所述第二重复单元具有式(1)的结构:其中R1、R2和R3各自独立地是氢、卤素、取代或未取代的C1至C12烷基或C3至C12环烷基,其任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N‑氧化物基团、磺酸酯基团、磺酰胺基团、或其组合、取代或未取代的C6至C14芳基、或C3至C12杂芳基,其中所述取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2‑C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;其中R1和R2一起任选地形成环;并且其中n=1‑3。
Description
背景技术
本公开涉及可用于抗蚀剂组合物中的聚合物,其制造方法以及包含其的制品。具体地,本公开涉及用于抗蚀剂组合物中的包含内酰胺和环状酰亚胺的聚合物、其制造方法以及包含其的制品。
现有技术的光刻构图工艺目前采用ArF(193nm)浸没式扫描仪来处理尺寸小于60纳米(nm)的晶片。将ArF光刻推向60nm以下的临界尺寸在以下方面对光致抗蚀剂的功能提出了一些挑战:工艺窗口、线宽粗糙度(LWR)以及用于大规模集成电路制造的其他关键参数。所有这些参数都必须在下一代配方中着手解决。随着高级节点中图案尺寸的减小,LWR值并未以相同的速率同时减小,从而在这些前沿节点的处理过程中形成了重要的变化来源。工艺窗口的改进对于实现集成电路制造的高产量也很有用。
因此,所希望的是制造显示出改善的LWR性能,提供更稳定的工艺窗口并且在过程溶剂中具有更好的溶解度的光致抗蚀剂组合物。
发明内容
本文公开了包含第一重复单元和第二重复单元的聚合物,其中所述第一重复单元包含酸不稳定基团,并且所述第二重复单元具有式(1)的结构:
其中R1、R2和R3各自独立地是氢、卤素、取代或未取代的C1至C12烷基或C3至C12环烷基,其任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N-氧化物基团、磺酸酯基团、磺酰胺基团、或其组合、取代或未取代的C6至C14芳基、或C3至C12杂芳基,其中所述取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2-C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;其中R1和R2一起任选地形成环;其中Y选自羰基、磺酰基、或取代或未取代的亚甲基,其中Y和R2一起任选地形成取代或未取代的4-7元单环或取代或未取代的9-12元双环,所述单环和双环任选地含有1、2、或3个选自N、O、和S的杂原子,其中每个环是饱和的、不饱和的或芳族的,并且其中每个环任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N-氧化物基团、磺酸酯基团、磺酰胺基团、或其组合,其中所述环上的取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2-C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;并且其中R4和R5各自独立地是氢、卤素、取代或未取代的C1至C3烷基-其中所述取代是卤素;并且其中n=1至3。
具体实施方式
定义
在本公开中,“光化射线”或“辐射”意指例如汞灯的亮线光谱,准分子激光代表的远紫外线、极紫外线(EUV光)、X射线、粒子射线(如电子束和离子束)等。另外,在本发明中,“光”意指光化射线或辐射。
氟化氩激光器(ArF激光器)是特殊类型的准分子激光器,有时称为激基络合物激光器。“准分子”是“激发二聚体”的缩写,而“激基络合物”是“激发络合物”的缩写。准分子激光器使用稀有气体(氩气、氪气或氙气)和卤素气体(氟气或氯气)的混合物,它们在适当的电刺激和高压条件下会在紫外线范围中发射相干的受激辐射(激光)。
此外,除非另有说明,否则本说明书中的“曝光”不仅包括汞灯的曝光、准分子激光代表的远紫外线、X射线、极紫外线(EUV光)等,而且还包括用粒子射线(如电子束和离子束)进行书写。
在本说明书中,“(值)至(值)”意指包括在“至”之前和之后描述的数值分别作为下限值和上限值的范围。
不是在两个字母或符号之间的破折号(“-”)用于表示取代基的连接点。例如,-(CH2)C3-C8环烷基通过亚甲基(CH2)基团的碳连接。
在本说明书中,“(甲基)丙烯酸酯”表示“丙烯酸酯和甲基丙烯酸酯中的至少一种”。另外,“(甲基)丙烯酸”意指“丙烯酸和甲基丙烯酸中的至少一种”。
“烷酰基”是如本文所定义的烷基,其共价键合至被酮基(-(C=O)-)桥取代的基团。烷酰基具有指定的碳原子数,其中酮基的碳包括在编号的碳原子中。例如,C2烷酰基是具有式CH3(C=O)-的乙酰基。
如本文所用,术语“烷基”意指具有指定的碳原子数(通常为1至约12个碳原子)的支链或直链饱和脂族烃基。如本文所用的术语C1-C6烷基表示具有1、2、3、4、5或6个碳原子的烷基。其他实施例包括具有1至8个碳原子、1至4个碳原子、或1或2个碳原子的烷基,例如C1-C6烷基、C1-C4烷基、和C1-C2烷基。当本文中将C0-Cn烷基与另一个基团(例如,(环烷基)C0-C4烷基)结合使用时,所示基团(在这种情况下为环烷基)可通过单个共价键(C0)直接键合,或通过具有指定的碳原子数的烷基链连接,在这种情况下为1、2、3或4个碳原子。烷基的实例包括但不限于:甲基、乙基、正丙基、异丙基、正丁基、3-甲基丁基、叔丁基、正戊基、和仲戊基。
如本文所用,术语“环烷基”表示具有仅碳环原子且具有指定的碳原子数(通常具有3至约8个环碳原子或3至约7个碳原子)的饱和烃环基。环烷基的实例包括:环丙基、环丁基、环戊基、或环己基以及桥连或笼形的饱和环基团,如降冰片烷或金刚烷。
如本文所用,术语“杂环烷基”表示含有选自N、O和S的1至约3个杂原子、其余的环原子为碳的饱和环状基团。杂环烷基具有3至约8个环原子,并且更典型地具有5至7个环原子。杂环烷基的实例包括吗啉基、哌嗪基、哌啶基、和吡咯烷基。杂环烷基中的氮可任选地被季铵化。
在本说明书中对基团和原子团的引用中,在未明确说明所述基团是取代还是未取代的情况下表示所述基团的情况下时,则所述基团包括不具有取代基的基团和原子团,以及具有取代基的基团和原子团。例如,未表示其是否是取代或未取代的“烷基”不仅包括不具有取代基的烷基(未取代的烷基),而且还包括具有取代基的烷基(取代的烷基)。
如本文所用,术语“烯基”意指包含一个或多个不饱和碳-碳键的直链和支链烃链,其可以在沿着链的任何稳定点出现。本文所述的烯基典型地具有2至约12个碳原子。示例性烯基是低级烯基,那些烯基具有2至约8个碳原子,例如C2-C8、C2-C6、和C2-C4烯基。烯基的实例包括乙烯基、丙烯基和丁烯基。
术语“炔基”意指包含一个或多个C≡C碳-碳三键(其可以在沿着链的任何稳定点出现)的直链和支链烃链。本文所述的炔基典型地具有2至约12个碳原子。示例性炔基是低级炔基,那些炔基具有2至约8个碳原子,例如C2-C8、C2-C6、和C2-C4炔基。炔基的实例包括乙炔基、丙炔基、和丁炔基。
如本文所用,术语“环烯基”意指包含一个或多个不饱和碳-碳键(其可以在环的任何稳定点上存在)并且具有指定的碳原子数的饱和烃环基团。单环环烯基典型地具有3至约8个碳环原子或3至7(3、4、5、6或7)个碳环原子。环烯基取代基可以是取代的氮或碳原子的侧基,或者可以具有两个取代基的取代的碳原子可以具有作为螺环基团连接的环烯基。环烯基的实例包括环丙烯基、环丁烯基、环戊烯基、或环己烯基以及桥连或笼形的饱和环基团,如降冰片烯。
如本文所用,术语“(环烷基)C0-Cn烷基”意指其中环烷基和烷基如本文所定义的取代基,并且(环烷基)烷基与它所取代的分子的连接点为单个共价键(C0烷基)或在烷基上。(环烷基)烷基包括但不限于环丙基甲基、环丁基甲基、和环己基甲基。
如本文所用,术语“(杂环烷基)C0-Cn烷基”意指其中杂环烷基和烷基如本文所定义的取代基,并且(杂环烷基)烷基与它所取代的分子的连接点为单个共价键(C0烷基)或在烷基上。(杂环烷基)烷基包括但不限于吗啉基甲基、哌嗪基甲基、哌啶基甲基、和吡咯烷基甲基。
如本文所用,术语“芳基”意指在一个或多个芳族环中包含仅碳的芳族基团。典型的芳基含有1-3个独立的、稠合的或侧基的环和6至约18个环原子,而没有杂原子作为环成员。当指出时,这样的芳基可以进一步被碳或非碳原子或基团取代。双环芳基可以进一步被碳或非碳原子或基团取代。双环芳基可以含有两个稠合的芳族环(萘基)或稠合至5-至7元非芳族环基团的芳族环,其任选地含有1或2个独立地选自N、O、和S的杂原子,例如3,4-亚甲基二氧基-苯基。芳基包括例如苯基、萘基(包括1-萘基和2-萘基)以及联苯基。
如本文所用,术语“单环或双环杂芳基”表示稳定的5至7元单环或7至10元双环的杂环,其包含至少1个包含1至4个或特别地1至3个选自N、O和S的杂原子、其余的环原子为碳的芳族环。当杂芳基中的S和O原子的总数超过1时,这些杂原子彼此不相邻。特别地,杂芳基中的S和O原子的总数不大于2,更特别地,杂芳基中的S和O原子的总数不大于1。杂芳基中的氮原子可以任选地被季铵化。当指出时,这样的杂芳基可以进一步被碳或非碳原子或基团取代。这样的取代可以包括与5至7元饱和的环状基团稠合,所述饱和的环状基团任选地包含1或2个独立地选自N、O和S的杂原子,以形成例如[1,3]二氧杂环戊烯并[4,5-c]吡啶基。在某些实施例中,使用5-至6元杂芳基。杂芳基的实例包括但不限于:吡啶基、吲哚基、嘧啶基、哒嗪基、吡嗪基、咪唑基、噁唑基、呋喃基、噻吩基、噻唑基、三唑基、四唑基、异噁唑基、喹啉基、吡咯基、吡唑基、苯并[b]噻吩基、异喹啉基、喹唑啉基、喹喔啉基、噻吩基、异吲哚基、和5,6,7,8-四氢异喹啉。
“卤代烷基”包括具有指定的碳原子数的支链和直链烷基,其被1个或多个卤素原子(直至最大允许的卤素原子数原子)取代。卤代烷基的实例包括但不限于:三氟甲基、二氟甲基、2-氟乙基、和五-氟乙基。
“卤代烷氧基”是通过氧桥(醇基的氧)连接的如本文所定义的卤代烷基。
“卤代”或“卤素”是氟、氯、溴、和碘中的任一个。
“单-和/或二-烷基氨基”是仲或叔烷基氨基,其中烷基独立地选自如本文所定义的具有指定的碳原子数的烷基。烷基氨基的连接点是在氮上。单-和二-烷基氨基的实例包括乙基氨基、二甲基氨基、和甲基-丙基-氨基。氨基意指-NH2。
如本文所用,术语“取代的”意指指定原子或基团上的任何一个或多个氢被来自指定基团的选择所替代,前提是不超过指定原子的正常价。在取代基是氧代(即,=O)时,那么原子上的2个氢被替代。当氧代基团取代芳族部分时,相应的部分不饱和环替代芳族环。例如,被氧代取代的吡啶基是吡啶酮。仅当取代基和/或变量的组合产生稳定的化合物或有用的合成中间体时,这些组合才是允许的。稳定的化合物或稳定的结构意指足够稳健以抵抗从反应混合物中分离出来的化合物。
除非另有说明,否则将取代基命名为核心结构。例如,应该理解的是,当(环烷基)烷基被列为可能的取代基时,所述取代基与核心结构的连接点在烷基部分中,或者当芳基烷基被列为可能的取代基时,其与核心结构的连接点是在该烷基部分中。
可以存在于“取代的”或“任选取代的”位置上的合适基团包括但不限于卤素;氰基;羟基;硝基;叠氮基;烷酰基(如C2-C6烷酰基,如酰基等);甲酰氨基;具有1至约8个碳原子或1至约6个碳原子的烷基(包括环烷基);烯基和炔基,包括具有一个或多个不饱和键和2至约8或2至约6个碳原子的基团;具有一个或多个氧键和1至约8或1至约6个碳原子的烷氧基;芳氧基,如苯氧基;烷硫基,包括具有一个或多个硫醚键和1至约8个碳原子或1至约6个碳原子的那些;烷基亚磺酰基,包括具有一个或多个亚磺酰基键和1至约8个碳原子或1至约6个碳原子的那些;烷基磺酰基,包括具有一个或多个磺酰基键和1至约8个碳原子或1至约6个碳原子的那些;氨基烷基,包括具有一个或多个N原子和1至约8或1至约6个碳原子的基团;具有6个或更多个碳原子和一个或多个环的芳基(例如,苯基,联苯基,萘基等,每个环是取代或未取代的芳族的);具有1至3个单独的或稠合的环和6至约18个环碳原子的芳基烷基,其中苄基为示例性的芳基烷基;具有1至3个单独的或稠合的环和6至约18个环碳原子的芳基烷氧基,其中苄氧基为示例性的芳基烷氧基;或具有1至3个独立的或稠合的环的饱和、不饱和或芳族杂环基,每个环具有3至约8个成员并且具有一个或多个N、O或S原子,例如香豆素基、喹啉基、异喹啉基、喹唑啉基、吡啶基、吡嗪基、嘧啶基、呋喃基、吡咯基、噻吩、噻唑基、三嗪基、噁唑基、异噁唑基、咪唑基、吲哚基、苯并呋喃基、苯并噻唑基、四氢呋喃基、四氢吡喃基、哌啶基、吗啉基、哌嗪基、和吡咯烷基。这样的杂环基可以进一步被例如羟基、烷基、烷氧基、卤素和氨基取代。
如本文所公开的包括共聚物和可聚合光酸产生剂单体的光致抗蚀剂组合物(本文也称为抗蚀剂组合物)可用于提供包括光致抗蚀剂的层。经涂覆的基底可以由光致抗蚀剂组合物形成。此种经涂覆的基底包括:(a)具有在其表面上要被图案化的一个层或多个层的基底;以及(b)在要图案化的一个层或多个层上的光致抗蚀剂组合物层。
本文公开了可用于光致抗蚀剂组合物中的抗蚀剂聚合物,所述光致抗蚀剂组合物适用于以减小的线宽粗糙度和改进的工艺窗口印刷精细特征。在实施例中,抗蚀剂聚合物包含共聚物,所述共聚物包括第一重复单元和第二重复单元,其中所述第一重复单元包含酸不稳定基团并且其中所述第二重复单元衍生自下式(1)的结构的聚合:
其中R1、R2和R3各自独立地是氢、卤素、取代或未取代的C1至C12烷基或C3至C12环烷基,其任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N-氧化物基团、磺酸酯基团、磺酰胺基团、或其组合、取代或未取代的C6至C14芳基、或C3至C12杂芳基,其中所述取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2-C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;
其中R1和R2一起任选地形成环;
其中Y选自羰基、磺酰基、或取代或未取代的亚甲基,
其中Y和R2一起任选地形成取代或未取代的4-7元单环或取代或未取代的9-12元双环(包括稠合和螺环的),所述单环和双环任选地含有1、2、或3个选自N、O、和S的杂原子,其中每个环是饱和的、不饱和的或芳族的,并且其中每个环任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N-氧化物基团、磺酸酯基团、磺酰胺基团、或其组合,其中所述环上的取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2-C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;并且其中R4和R5各自独立地是氢、卤素、取代或未取代的C1至C3烷基-其中所述取代是卤素;并且其中n=1、2或3。
在实施例中,第二重复单元是具有环外可聚合基团的环状内酰胺和/或环状酰亚胺。在实施例中,抗蚀剂聚合物可包含多个重复单元,所述多个重复单元包含彼此不同的环状内酰胺和/或环状酰亚胺(具有环外可聚合基团)。
本文公开的抗蚀剂聚合物有时也称为抗蚀剂共聚物。将第一重复单元和第二重复单元共价或离子键合以形成共聚物。所述共聚物可以是嵌段共聚物、无规共聚物、星形嵌段共聚物、梯度共聚物、交替共聚物或其组合。在实施例中,也可以将含有共聚物的光致抗蚀剂组合物与一种或多种聚合物共混。可以与抗蚀剂聚合物共混的聚合物优选与第一重复单元、第二重复单元和/或第三重复单元相容。在优选的实施例中,抗蚀剂聚合物是无规共聚物。
本文公开的抗蚀剂聚合物的优点在于环状内酰胺和环状酰亚胺重复单元具有双重目的,既充当极性官能团以调节酸扩散,并且又充当抗蚀剂聚合物主链中的高Tg(玻璃化转变温度)组分以改善线宽粗糙度和工艺窗口。当与包含传统内酯或极性聚合物的其他可商购的抗蚀剂组合物相比,在抗蚀剂聚合物中使用环状内酰胺或环状酰亚胺重复单元提高了聚合物在光致抗蚀剂组合物中使用的溶剂中的聚合物溶解度。本文公开的聚合物在有机溶剂中的改善的溶解度使其适用于溶剂可显影的负性抗蚀剂组合物中。
在实施例中,抗蚀剂聚合物可以包括(除了具有以上式(1)所示的结构的第二重复单元之外)彼此不同的多个重复单元,其中每个不同的重复单元具有酸不稳定基团。在实施例中,抗蚀剂聚合物可以包括(除了具有以上式(1)所示的结构的第二重复单元之外)彼此不同的多个重复单元,其中不同的重复单元中的至少一个具有酸不稳定基团。在实施例中,抗蚀剂聚合物除了具有上述式(1)所示的结构的第二重复单元以外,还可以包括两个或更多彼此不同的单体重复单元(例如,第一重复单元和第三重复单元),其中所述第一或第三重复单元中的至少一个具有酸不稳定基团。在实施例中,除了具有以上式(1)所示的结构的第二重复单元之外,抗蚀剂聚合物中的第一和第三重复单元两者彼此不同并且各自包含酸不稳定基团。
在一些实施例中,抗蚀剂聚合物可以包括两种或更多种单体重复单元,例如像,第一重复单元、第三重复单元和/或第四重复单元,其中第一、第三或第四重复单元中的一个具有除了第二重复单元(其包含具有内环可聚合基团的环状内酰胺和/或环状酰亚胺)以外,还包含酸不稳定基团。如上所述,第一重复单元、第二重复单元、第三重复单元和/或第四重复单元彼此共价或离子键合以形成抗蚀剂聚合物。在一些实施例中,抗蚀剂共聚物可以包含在辐射下分解以形成酸的重复单元。
抗蚀剂聚合物可包含不止一种的内酰胺和/或环状酰亚胺。所述聚合物可以额外包含含有内酯、磺内酯或光酸产生剂基团的重复单元。可能存在各自在化学上彼此不同的多个重复单元,其包含内酯、磺内酯或光酸产生剂。
第二重复单元(具有以上式(1)所示的结构)的实例包括内酰胺单体和下式(2)所示的环状酰亚胺单体:
在优选的实施例中,第二重复单元具有以下结构:
在实施例中,第二重复单元与其他重复单元(第一重复单元、第三重复单元、第四重复单元和/或第五重复单元)之和的摩尔比(以百分比表示)为1%至40%、优选5%至30%、并且更优选10%至20%。在实施例中,第二重复单元占抗蚀剂共聚物中重复单元总数的1%至40%、优选5%至30%、并且更优选10%至20%。
在实施例中,抗蚀剂聚合物中第二重复单元与其他重复单元(第一重复单元、第三重复单元和/或第四重复单元)之和的重量比为1:3至1:10、优选1:4至1:8、并且更优选1:5至1:7。在另一个实施例中,第二重复单元的原子量与抗蚀剂聚合物的总原子量的重量比为0.05至0.20、优选0.08至0.16、并且优选0.09至0.15。
在又另一个实施例中,基于抗蚀剂共聚物的总重量,第二重复单元在抗蚀剂共聚物中的用量为5至60wt%、优选用量为8至35wt%、并且更优选用量为10至25wt%。
如上所述,第一重复单元、第三重复单元和/或第四重复单元中的一个具有酸不稳定基团。应当注意,尽管本公开涉及第一、第三和第四重复单元,但是可以存在额外的重复单元,如第五、第六等重复单元等,其中在抗蚀剂聚合物中的每个重复单元与其他重复单元在化学上不同。酸不稳定基团可以是叔烷基酯、缩醛基团或缩酮基团或其组合。具有酸不稳定基团的重复单元(例如,第一重复单元、第三重复单元和/或第四重复单元)的实例是(甲基)丙烯酸酯和/或乙烯基芳族单体。
在实施例中,具有不稳定酸基团的第一重复单元具有由式(4)表示的结构:
其中R6是氢或具有1至10个碳原子的烷基或卤代烷基并且其中L包含羰基(例如以下物种,包括醛类;酮类;羧酸类和羧酸酯类,例如像(甲基)丙烯酸和(甲基)丙烯酸酯)、单键(例如乙烯基醚)或芳族单元(例如苯乙烯或其衍生物)。在实施例中,羧酸酯是叔烷基酯。
在实施例中,当L包含羰基时,含有酸不稳定基团的重复单元具有由下式(5a)表示的结构:
其中R7是氢或具有1至10个碳原子的烷基或卤代烷基并且其中R8是具有1至10个碳原子的直链或支链的取代或未取代的烷基、具有3至14个碳原子的取代或未取代的单环或多环的环烷基或叔烷基酯。环烷基可包含一个或多个杂原子,如氧、硫、氮或磷。还可以使用杂原子的组合。例如,环烷基可以包含氧和氮杂原子。不具有酸不稳定基团的具有式(5a)的结构的重复单元也可以用于抗蚀剂聚合物中,只要所述抗蚀剂聚合物具有至少一个具有酸不稳定基团的重复单元即可。
下式(6)中示出了含有酸不稳定基团(例如羰基)的其他单体的实例:其中R9是氢或具有1至10个碳原子的烷基或卤代烷基,并且其中R10、R11和R12可以是相同或不同的并且选自具有1至10个碳原子的直链或支链的取代或未取代的烷基、具有3至14个碳原子的取代或未取代的单环或多环的环烷基、芳基或杂芳基。环烷基可包含一个或多个杂原子,如氧、硫、氮或磷。还可以使用杂原子的组合。例如,环烷基可以包含氧和氮杂原子。在实施例中,R10和R11或R10和R12可以任选地形成环。
在实施例中,式(6)中的R10、R11和R12可以相同或不同并且包含具有2至8个碳原子的可为直链或支链的取代或未取代的烷基,或为具有4、5或6个碳原子的可包含分支的取代或未取代的环烷基。
包含羰基酸不稳定基团的单体的实例包括:
或其组合;其中R1是氢或具有1至10个碳原子的烷基、卤素、或具有1至10个碳原子的卤代烷基;并且其中R7是包括具有1至10个碳原子的支链结构的烷基或具有3至14个碳原子的单环或多环的环烷基;并且R9是可以包括具有1至10个碳原子的支链结构的烷基或具有3至14个碳原子的单环或多环的环烷基。优选的卤素原子是氟原子,并且优选的卤代烷基包括氟代烷基。
在实施例中,含有酸不稳定基团的重复单元具有由下式(5b)表示的结构
其中Z是包含至少一个碳原子和至少一个杂原子的连接单元,其中R7是氢原子或具有1至10个碳原子的烷基;并且其中R8是可以包括具有1至10个碳原子的支链结构的烷基或具有3至14个碳原子的单环或多环的环烷基或叔烷基酯。在实施例中,Z可以具有2至10个碳原子。在另一个实施例中,Z可以是CH2-C(=O)-O-)。
具有式5b结构的重复单元的具体实例如下:
说明性的酸不稳定的缩醛和缩酮取代的单体还包括:
及其组合,其中Ra是-H、-F、-CH3、或-CF3。
在另一个实施例中,当L为芳族单元时,酸不稳定重复单元可以为具有式(7)结构的乙烯基芳族单元:
其中R13是氢或具有1至10个碳原子的烷基、卤素、或具有1至10个碳原子的卤代烷基;Z1是羟基或羧基或任选地氢、卤素、烷基、芳基、或稠合芳基;并且p是1至约5。在实施例中,Z1优选是羟基并且p优选是1或2。
可以反应生成抗蚀剂聚合物的乙烯基芳族单体包括苯乙烯、烷基苯乙烯、羟基苯乙烯、或被卤素取代的苯乙烯。合适的烷基苯乙烯的实例是邻甲基苯乙烯、对甲基苯乙烯、间甲基苯乙烯、α-甲基苯乙烯、邻乙基苯乙烯、间乙基苯乙烯、对乙基苯乙烯、α-甲基-对甲基苯乙烯、2,4-二甲基苯乙烯、对叔丁基苯乙烯、4-叔丁基苯乙烯、等或包含至少一种前述烷基苯乙烯单体的组合。被卤素取代的苯乙烯的实例包括氯苯乙烯、氟苯乙烯、羟基氟苯乙烯、或其组合。
酸不稳定的重复单元可以以基于抗蚀剂聚合物的总摩尔数5至70mol%、优选20至60mol%的量存在,而包含环状内酰胺或环状酰亚胺的重复单元以基于抗蚀剂聚合物的总摩尔数5至30mol%,优选为10至20mol%的量存在。
在一个实施例中,在一种制造抗蚀剂共聚物的方法中,将未反应的酸不稳定重复单元(第一、第三、第四和/或第五重复单元)以及化学计量的环状内酰胺和/或环状酰亚胺重复单元引入反应容器中。可以将酸不稳定的重复单元和内酰胺和/或酰亚胺重复单元均溶剂化的合适的溶剂与合适的引发剂一起添加到反应器中。也可以将活化或增加反应速率的催化剂添加到反应器中。如上所述,不包含酸不稳定基团的单元(如内酯、磺内酯、光酸产生剂单体等)可以与酸不稳定重复单元(包含酸不稳定基团的重复单元)和环状内酰胺和环状酰亚胺基结合使用,以形成抗蚀剂聚合物。
应当注意,酸不稳定的重复单元以及环状内酰胺和环状酰亚胺重复单元可以在单独的过程中制造,或者可以在反应以生产抗蚀剂聚合物之前在商业上购买。可将可商购的单体纯化,之后使其反应以形成抗蚀剂聚合物。
将聚合引发剂与任选的催化剂一起添加到反应容器中,并且升高容器温度以促进形成抗蚀剂聚合物的反应。合适的时间段后,逐渐降低温度,并将所得共聚物与溶液分离并干燥。可以在用于抗蚀剂组合物中之前通过洗涤来纯化聚合物。
示例性抗蚀剂共聚物在以下式(8)至(11)中示出:
抗蚀剂聚合物中的第一重复单元(酸不稳定的重复单元)的重复单元的数可以为20至60、优选30至50。抗蚀剂聚合物中的第二重复单元(内酰胺或酰亚胺重复单元)的重复单元的数可以为10至30、优选15至25。如果在抗蚀剂聚合物中使用第三重复单元(酸不稳定的重复单元),则第三重复单元的数可以为20至60、优选30至50。如果在抗蚀剂聚合物中使用第四重复单元(酸不稳定的重复单元),则第四重复单元的数可以为5至15、优选8至12。在式(6)至(9)中,“x”可以为20至60、优选为30至50,“y”可以为20至60、优选为30至50,“p”可以为5至15、优选为8至12并且z可以为10至30、优选15至25。
通过上述反应产生的抗蚀剂组合物中使用的示例性抗蚀剂共聚物在下式(12)中示出。
抗蚀剂共聚物可以进一步包括衍生自包含光酸产生剂的单体的重复单元。包含可聚合基团的光酸产生剂单体可以由式(13)表示:
在式(13)中,每个Ra可独立地为H、F、C1-10烷基或C1-10氟烷基。如本说明书通篇所使用的,“氟”或“氟化”意指一个或多个氟基团连接到缔合基团上。例如,根据该定义并且除非另有说明,“氟代烷基”包括单氟代烷基、二氟代烷基等,以及其中烷基的基本上所有碳原子都被氟原子取代的全氟代烷基;类似地,“氟芳基”意指单氟芳基、全氟芳基等。在此上下文中,“基本上所有”意指与碳相连的所有原子的大于或等于90%、优选地大于或等于95%、并且还更优选地大于或等于98%是氟原子。
在式(13)中,Q2可以是单键或含酯或不含酯的氟化或非氟化的基团,其选自C1-20烷基、C3-20环烷基、C6-20芳基和C7-20芳烷基。例如,在包括酯的情况下,所述酯可以在Q2与双键的连接点之间形成连接键。这样,在Q2为酯基团的情况下,式(13)可以为(甲基)丙烯酸酯单体。在不包含酯的情况下,Q2可以是芳族的,使得式(13)可以是例如苯乙烯单体或乙烯基萘单体。
另外,在式(13)中,A可以是含酯或不含酯的氟化或非氟化的基团,其选自C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基。有用的A基团可包括氟化芳族部分、直链氟代烷基或支链氟代烷基酯。例如,A可以是-[(C(Re)2)x(=O)O]c-(C(Rf)2)y(CF2)z-基团,或者可以是邻、间或对取代的-C6Rg 4-基团,其中每个Re、Rf、和Rg各自独立地为H、F、C1-6氟烷基或C1-6烷基,c可以为0或1,x可以是1至10的整数,y和z可以独立地是0至10的整数,并且y+z的总和可以至少为1。
另外,在式(13)中,Z-可以是阴离子基团,包括磺酸根的阴离子(-SO3 -)、磺酰胺的的阴离子(-SO2(N-)R’)其中R'可以是C1-10烷基或C6-20芳基、或磺酰亚胺的阴离子。当Z-是磺酰亚胺时,磺酰亚胺可以是具有通用结构A-SO2-(N-)-SO2-Y2的不对称磺酰亚胺,其中A是如上文所描述的,并且Y2可以是直链或支链C1-10氟烷基。例如,Y2基团可以是C1-4全氟烷基,其可以衍生自相应的全氟链烷磺酸,如三氟甲磺酸或全氟丁烷磺酸。
在实施例中,式(13)的单体可以具有式(13a)或(13b)的结构:
其中A和Ra是如式(13)所定义。在式(13)、(13a)、和(13b)中,G+可以具有式(13c):
其中X、Rc和z与以上实施例中描述的相同。在实施例中,共聚物可以包括具有以下结构中的任何一种的聚合产物:
如上所述,抗蚀剂聚合物可用于抗蚀剂组合物中,然后将其布置在基底上以图案化所述基底。然后通过将抗蚀剂聚合物混合并溶解在合适的溶剂中来制备抗蚀剂组合物。除了抗蚀剂聚合物和溶剂之外,抗蚀剂组合物可任选地包含光酸产生剂、表面活性剂、任选的包含一种或多种氟化单体单元以形成抗蚀剂组合物的添加剂聚合物,以及任选地产生碱性化合物的分子。
在一些实施例中,基于总固体的重量,溶液中的抗蚀剂组合物包含50至99重量%、特别地55至95重量%、更特别地65至90重量%的量的聚合物。将理解的是,在抗蚀剂中的组分的上下文中使用的“聚合物”可以仅意指本文公开的共聚物、或共聚物与在光致抗蚀剂中有用的另一种聚合物的组合。将理解的是,总固体包括聚合物、光-可破坏的碱、淬灭剂、表面活性剂、任何添加的PAG和任何任选的添加剂(不包括溶剂)。
通常适用于溶解、分配和涂覆的溶剂包括苯甲醚,醇(包括乳酸乙酯、2-羟基丁酸甲酯(HBM)、1-甲氧基-2-丙醇(也称为丙二醇甲醚,PGME)和1-乙氧基-2-丙醇),酯(包括乙酸正丁酯、1-甲氧基-2-丙基乙酸酯(也称为丙二醇甲醚乙酸酯,PGMEA)、甲氧基乙基丙酸酯、乙氧基乙基丙酸酯和γ-丁内酯),酮(包括环己酮和2-庚酮),以及其组合。
基于抗蚀剂组合物的总重量,溶剂的量可以为例如70至99重量%、特别是85至98重量%。
如上所述,抗蚀剂组合物可以包含含氟聚合物。在实施例中,含氟聚合物可以衍生自具有式(14)结构的单体的聚合。
其中在式(14)中,R13是氢或具有1至10个碳原子的烷基或卤代烷基并且R14是C2-10氟烷基。含氟单体的实例是甲基丙烯酸三氟乙酯、甲基丙烯酸十二氟庚酯或其组合。
氟化聚合物在抗蚀剂组合物中以基于所述抗蚀剂组合物的总重量0.01至10wt%的量存在。在优选的实施例中,氟化聚合物在抗蚀剂组合物中以基于所述抗蚀剂组合物的总重量1至5wt%的量存在。
所述抗蚀剂组合物还可包含光酸产生剂。光酸产生剂通常包括适合于制备光致抗蚀剂目的的那些光酸产生剂。光酸产生剂包括,例如,非离子肟和各种鎓离子盐。鎓离子包括例如未取代的和取代的铵离子、未取代的和取代的鏻离子、未取代的和取代的砷离子、未取代的和取代的锑离子、未取代的和取代的铋离子、未取代的和取代的氧鎓离子、未取代的和取代的锍离子、未取代的和取代的硒离子、未取代的和取代的碲离子、未取代的和取代的氟鎓离子、未取代的和取代的氯鎓离子、未取代的和取代的溴鎓离子、未取代的和取代的碘鎓离子、未取代的和取代的氨基重氮离子(取代的氢叠氮化)、未取代的和取代的氢氰鎓离子(取代的氢叠氮化)、未取代的和取代的重氮离子(RN=N+R2)、未取代的和取代的亚胺离子(R2C=N+R2)、具有两个双键取代基的季铵离子(R=N+=R)、硝鎓(nitronium)离子(NO2 +)、双(三芳基膦)亚胺离子((Ar3P)2N+)、未取代的或取代的具有一个三键取代基的叔铵(R≡NH+)、未取代的和取代的氮杂炔离子(RC≡NR+)、未取代的和取代的重氮离子(N≡N+R)、具有两个部分双-键的取代基的叔铵离子未取代的和取代的吡啶鎓离子、具有一个三键取代基和一个单键取代基的季铵离子(R≡N+R)、具有一个三键取代基的叔氧鎓离子(R≡O+)、亚硝鎓(nitrosonium)离子(N≡O+)、具有两个部分双键的取代基的叔氧鎓离子吡喃鎓离子(C5H5O+)、具有一个三键取代基的叔锍离子(R≡S+)、具有两个部分双键的取代基的叔锍离子和硫代亚硝鎓离子(N≡S+)。在一些实施例中,鎓离子选自未取代或取代的二芳基碘鎓离子和未取代或取代的三芳基锍离子。可以在美国专利号Crivello等的4,442,197、Crivello的4,603,101和Zweifel等的4,624,912中找到合适的鎓盐的实例。
合适的光酸产生剂在化学增强的光致抗蚀剂领域中是已知的并且包括例如:鎓盐,例如三苯基锍三氟甲磺酸盐、(对-叔丁氧基苯基)二苯基锍三氟甲磺酸盐、三(对-叔丁氧基苯基)锍三氟甲磺酸盐、三苯基锍对-甲苯磺酸盐;硝基苄基衍生物,例如2-硝基苄基-对-甲苯磺酸酯、2,6-二硝基苄基-对-甲苯磺酸酯和2,4-二硝基苄基-对-甲苯磺酸酯;磺酸酯,例如,1,2,3-三(甲磺酰氧基)苯、1,2,3-三(三氟甲磺酰基)苯和1,2,3-三(对甲苯磺酰氧基)苯;重氮甲烷衍生物,例如,双(苯磺酰基)重氮甲烷、双(对-甲苯磺酰基)重氮甲烷;乙二肟衍生物,例如双-O-(对-甲苯磺酰基)-α-二甲基乙二肟和双-O-(正丁烷磺酰基)-α-二甲基乙二肟;N-羟基酰亚胺化合物的磺酸酯衍生物,例如N-羟基琥珀酰亚胺甲磺酸酯、N-羟基琥珀酰亚胺三氟甲磺酸酯;以及含卤素的三嗪化合物,例如2-(4-甲氧基苯基)-4,6-双(三氯甲基)-1,3,5-三嗪、和2-(4-甲氧基萘基)-4,6-双(三氯甲基)-1,3,5-三嗪。具有具体实例的合适的光酸产生剂在Hashimoto等人的美国专利号8,431,325中,在第37栏11-47行和41-91栏进一步描述。
在另一个优选实施例中光酸产生剂是由式G+A-表示的化合物,其中A-是非聚合的有机阴离子并且G+具有式(VI):
其中在式(13c)中,X可以为S或I,每个Rc可以为卤代或非卤代的,并且独立地为C1-30烷基;多环或单环C3-30环烷基;多环或单环的C4-30芳基,其中当X为S时,Rc基团中的一个任选地通过单键连接至一个相邻的Rc基团,z为2或3,其中当X为I时,z为2,或当X为S时,z为3。
例如阳离子G+可以具有式(13d)、(13e)、或13f):
其中当X是I或S时,Rh、Ri、Rj和Rk是未取代的或取代的并且各自独立地是羟基、腈、卤素、C1-30烷基、C1-30氟烷基、C3-30环烷基、C1-30氟环烷基、C1-30烷氧基、C3-30烷氧基羰基烷基、C3-30烷氧基羰基烷氧基、C3-30环烷氧基、C5-30环烷氧基羰基烷基、C5-30环烷氧基羰基烷氧基、C1-30氟烷氧基、C3-30氟烷氧基羰基烷基、C3-30氟烷氧基羰基烷氧基、C3-30氟环烷氧基、C5-30氟环烷氧基羰基烷基、C5-30氟环烷氧基羰基烷氧基、C6-30芳基、C6-30氟芳基、C6-30芳氧基、或C6-30氟芳氧基,其每一个是未取代的或取代的;
Ar1和Ar2独立地是C10-30稠合的或单键连接的多环芳基;
Rl是孤对电子,其中X是I,或C6-20芳基,其中X是S;
p是2或3的整数,其中当X是I时,p是2,并且当X是S,p是3,
q和r各自独立地是0至5的整数,并且
s和t各自独立地是0至4的整数。
在式(13c)、(13d)、或(13f)中,Rh、Ri、Rj和Rk中的至少一项可以是可酸切割的基团。在实施例中,可酸切割的基团可以是(i)叔C1-30烷氧基(例如叔丁氧基)、叔C3-30环烷氧基、叔C1-30氟烷氧基,(ii)叔C3-30烷氧基羰基烷基、叔C5-30环烷氧基羰基烷基、叔C3-30氟烷氧基羰基烷基,(iii)叔C3-30烷氧基羰基烷氧基、叔C5-30环烷氧基羰基烷氧基、叔C3-30氟烷氧基羰基烷氧基,或(iv)包括部分-O-C(R11R12)-O-的C2-30缩醛基团(或C1-30芳基)。
两个具体的PAGS是以下的PAG1和PAG2,其制备方法在2012年9月15日提交的美国专利申请序列号61/701,588中进行了描述。
其他合适的磺酸酯PAGS包括磺化的酯和磺酰氧基酮。参见J.of PhotopolymerScience and Technology[光聚合物科学和技术杂志],4(3):337-340(1991),公开了合适的磺酸酯PAGS,包括苯偶姻甲苯磺酸酯、叔丁基苯基α-(对-甲苯磺酰基氧基)-乙酸酯和叔丁基α-(对甲苯磺酰基氧基)-乙酸酯。优选的磺酸酯PAG还在美国专利号Sinta等人的美国专利号5,344,742中公开。
其他有用的光酸产生剂包括硝基苄基酯家族和s-三嗪衍生物。合适的s-三嗪光酸产生剂公开于例如美国专利号4,189,323中。卤化的非离子的、产生光酸的化合物也是合适的,例如像1,1-双[对氯苯基]-2,2,2-三氯乙烷(DDT);1,1-双[对甲氧基苯基]-2,2,2-三氯乙烷;1,2,5,6,9,10-六溴环癸烷;1,10-二溴癸烷;1,1-双[对氯苯基]-2,2-二氯乙烷;4,4-二氯-2-(三氯甲基)二苯甲醇;六氯二甲基砜;2-氯-6-(三氯甲基)吡啶;o,o-二乙基-o-(3,5,6-三氯-2-吡啶基)硫代磷酸酯;1,2,3,4,5,6-六氯环己烷;N(1,1-双[对氯苯基]-2,2,2-三氯乙基)乙酰胺;三[2,3-二溴丙基]异氰脲酸酯;2,2-双[对氯苯基]-1,1-二氯乙烯;三[三氯甲基]s-三嗪;以及其异构体、类似物、同系物和化合物。合适的光酸产生剂还公开在欧洲专利申请号0164248和0232972中。对于深度U.V.暴露特别优选的光酸产生剂包括1,1-双(对氯苯基)-2,2,2-三氯乙烷(DDT);1,1-双(对甲氧基苯酚)-2,2,2-三氯乙烷;1,1-双(氯苯基)-2,2,2三氯乙醇;三(1,2,3-甲烷磺酰基)苯;和三(三氯甲基)三嗪。
光酸产生剂可进一步包括可光破坏的碱。可光-破坏的碱包括可光分解的阳离子、并且优选是指用于制备PAG有用的那些,其与弱(pKa>2)酸的阴离子配对,例如像,C1-20羧酸。示例性的此类羧酸包括甲酸、乙酸、丙酸、酒石酸、琥珀酸、环己基羧酸、苯甲酸、水杨酸和其他此类羧酸。示例性的可光破坏的碱包括将以下结构的阳离子和阴离子结合在一起的那些,其中阳离子是三苯基鋶或以下之一:
其中R独立地是H、C1-20烷基、C6-20芳基,或C6-20烷基芳基,并且阴离子是
其中R独立地是H、C1-20烷基、C1-20烷氧基、C6-20芳基、或C6-20烷基芳基。
抗蚀剂组合物可以任选地包括光碱产生剂,包括基于非离子光分解生色团的那些,例如像2-硝基苄基和苯偶姻基团。示例性的光碱产生剂是氨基甲酸邻硝基苄基酯。
基于固体的总重量,光酸产生剂以0至50重量%、特别是1.5至45重量%、更特别是2至40重量%的量包含在内。
抗蚀剂组合物可以包含光引发剂。在光致抗蚀剂组合物中使用光引发剂以通过产生自由基来引发交联剂的聚合。合适的自由基光引发剂包括例如偶氮化合物、含硫化合物、金属盐和络合物、肟、胺、多核化合物、有机羰基化合物及其混合物,如美国专利号4,343,885,第13栏26行至第17栏18行描述的那些;以及9,10-蒽醌;1-氯蒽醌;2-氯蒽醌;2-甲基蒽醌;2-乙基蒽醌;2-叔丁基蒽醌;八甲基蒽醌;1,4-萘醌;9,10-菲醌;1,2-苯并蒽醌;2,3-苯并蒽醌;2-甲基-1,4-萘醌;2,3-二氯萘醌;1,4-二甲基蒽醌;2,3-二甲基蒽醌;2-苯基蒽醌;2,3-二苯基蒽醌;3-氯-2-甲基蒽醌;惹烯醌(retenequinone);7,8,9,10-四氢萘醌;以及1,2,3,4-四氢苯并(a)蒽-7,12-二酮。其他光引发剂描述于美国专利号2,760,863中并且包括连位缩酮醇(vicinal ketaldonyl alcohol),如苯偶姻、新戊酸酯,酰胆碱醚,例如苯偶姻甲基醚和乙基醚;以及α-烃取代的芳族偶姻(acyloin),包括α-甲基苯偶姻、α-烯丙基苯偶姻和α-苯基苯偶姻。光还原性染料和还原剂(在美国专利号2,850,445;2,875,047;以及3,097,096中公开的),以及吩嗪、噁嗪和醌类的染料;二苯甲酮、具有氢供体的2,4,5-三苯基咪唑基二聚体及其混合物(如美国专利号3,427,161;3,479,185;和3,549,367中描述的)也可以用作光引发剂。
抗蚀剂组合物可以进一步任选地包括表面活性剂。示例性表面活性剂包括氟化和非氟化的表面活性剂,并且优选非离子表面活性剂。示例性的氟化非离子表面活性剂包括全氟C4表面活性剂,如FC-4430和FC-4432表面活性剂,自3M公司可得;以及氟二醇,如来自美国欧诺法公司(Omnova)的POLYFOXTM PF-636、PF-6320、PF-656、和PF-6520含氟表面活性剂。
基于固体的总重量,表面活性剂可以以0.01至5重量%、特别是0.1至4重量%、更特别是0.2至3重量%的量包含在内。
然后可以将抗蚀剂组合物用于图案化用作半导体的基底。另一个实施例是经涂覆的基底,包括:(a)具有在其表面上要被图案化的一个层或多个层的基底;以及(b)在要图案化的一个层或多个层上的抗蚀剂组合物层。
基底可以是如半导体之类的材料,如硅或化合物半导体(例如,III-V或II-VI)、玻璃、石英、陶瓷、铜等。典型地,基底是半导体晶片,如单晶硅或化合物半导体晶片,其具有一个或多个层以及在其表面上形成的图案化特征。任选地,例如,当需要在基础基底材料中形成沟槽时,可以对基础基底材料本身进行图案化。在基础基底材料上方形成的层可以包括例如一个或多个导电层,如铝、铜、钼、钽、钛、钨以及这些金属的合金、氮化物或硅化物、掺杂的非晶硅或掺杂的多晶硅的层;一个或多个介电层,如氧化硅、氮化硅、氮氧化硅或金属氧化物的层;半导体层,如单晶硅;底层;抗反射层,如底部抗反射层;以及其组合。可以通过以下各种技术形成这些层,例如化学气相沉积(CVD)(如等离子体增强CVD)、低压CVD或外延生长、物理气相沉积(PVD)(如溅射或蒸发)、电镀或旋涂。
本发明进一步包括一种形成电子装置的方法,所述方法包括:(a)在基底上施加本文所述的任何光致抗蚀剂组合物的层;(b)将所述光致抗蚀剂组合物层以图案方式暴露于活化(例如紫外或电子束)辐射;(c)使所暴露的光致抗蚀剂组合物层显影以提供抗蚀剂浮雕图像。所述方法可以任选地进一步包括(d)将所述抗蚀剂浮雕图案蚀刻到下面的基底中。在实施例中,活化辐射是具有193nm波长的ArF辐射。
可以通过任何合适的方法来完成将光致抗蚀剂组合物施加到基底上,包括:旋涂、喷涂、浸涂和刮涂。在一些实施例中,通过使用涂布轨道将光致抗蚀剂在溶剂中旋涂来完成光致抗蚀剂组合物层,其中将所述光致抗蚀剂组合物分配在旋转的晶片上。在分配期间,可以以最高达4,000转/分钟(rpm)、特别是500至3,000rpm、并且更特别是1,000至2,500rpm的速度旋转晶片。旋转经涂覆的晶片以去除溶剂,并且在热板上烘烤以去除残留的溶剂和薄膜上的自由体积,从而使其均匀致密。
然后使用曝光工具,如步进器,进行图案方式的曝光,其中通过图案掩模辐射膜,并且从而以图案方式进行曝光。在一些实施例中,所述方法使用先进的曝光工具,其产生能够以高分辨率波长的活化辐射,包括极端紫外线(EUV)或电子束(e-束)辐射。应当理解,使用活化辐射进行曝光会在曝光区域分解PAG并产生酸和分解副产物,并且然后在曝光后烘烤(PEB)步骤期间酸会影响聚合物的化学变化(解封(deblocking)酸敏感基团以产生碱溶性基团,或作为替代方案催化暴露区域的交联-反应)。这种曝光工具的分辨率可以是小于30纳米。
然后,通过用合适的显影剂处理曝光层来显影暴露的光致抗蚀剂层,所述显影剂能够选择性地去除膜的曝光部分(其中光致抗蚀剂为正性)或去除膜的未曝光部分(其中光致抗蚀剂在曝光区域中可交联,即负性的(negative tone))。在一些实施例中,基于具有酸-敏感(可脱保护的)基团的聚合物,光致抗蚀剂是正性的,并且显影剂优选为金属离子-游离的四烷基氢氧化铵溶液,例如像0.26标定四甲基氢氧化铵水溶液。作为替代方案,可以通过使用合适的有机溶剂显影剂进行负性显影(NTD)。NTD导致光致抗蚀剂层的未曝光区域的去除,从而由于那些区域的极性反转而留下了曝光区域。合适的NTD显影剂包括例如酮、酯、醚、烃及其混合物。其他合适的溶剂包括用于光致抗蚀剂组合物中的那些。在一些实施例中,显影剂为2-庚酮或乙酸丁酯,如乙酸正丁酯。不论显影是正性还是负性,通过显影形成图案。
当在一种或多种这样的图案形成过程中使用时,光致抗蚀剂可以用于制造电子和光电装置,如存储设备、处理器芯片(包括中央处理单元或CPU)、图形芯片以及其他这样的设备。
本文公开的抗蚀剂组合物通过以下非限制性实例举例说明。
实例
实例1
进行所述实例以说明用于抗蚀剂组合物中的环状酰亚胺重复单元的合成。
合成环状酰亚胺重复单元的反应描述如下。结构分别编号为1、2和3并且这些编号用于标识正在合成的产物。
化合物2的合成:将化合物-1(450g,4.5918mol)溶解于乙酸乙酯(EtOAC)(6.75L)中,然后在0℃下滴加在2M四氢呋喃(THF)(2.52L,5.0510mol)中的乙胺。将反应混合物在室温下搅拌1小时。反应完成后,将反应混合物过滤并真空干燥,以得到中间体N-取代的氨基丁烯酸。在单独的烧瓶中,将乙酸钠(NaOAC)和乙酸酐(AC2O)的混合物加热至80℃。在80℃下将N-取代的氨基丁烯酸添加到所述溶液中。将反应混合物在80℃下搅拌1小时。在反应完成后,将反应混合物冷却至室温并且用冰冷水稀释并且用乙酸乙酯萃取。将有机层经硫酸钠干燥并且浓缩以得到残余物。将残余物通过使用硅胶的柱(0至15%乙酸乙酯:石油醚)纯化以得到150g(26%)的2,为黄色固体。
化合物3的合成:将化合物-2(150g,1.2mol)溶解于乙酸(ACOH)(480mL)中,然后室温下添加三苯基膦(TPP)(315g,1.2mol)并且将混合物搅拌1小时。然后滴加福尔马林(HCOH)(90mL)。将反应混合物在室温下搅拌2.5小时。反应完成后,将反应混合物用水稀释并且用二氯甲烷萃取。将有机层经硫酸钠干燥,在低真空下浓缩以得到残余物。将残余物通过使用硅胶的柱(0至15%乙酸乙酯:石油醚)纯化以得到化合物3,150g(89.9%)为浅黄色液体。
实例2
进行所述实例以说明抗蚀剂聚合物(抗蚀剂共聚物)的制造,并比较抗蚀剂聚合物与不含有内酰胺单体和/或酰亚胺单体的抗蚀剂聚合物的溶解度。用22.8g乳酸乙酯、9.8gγ-丁内酯(GBL)、9.56g化合物-4、8.92g化合物-6和3.65g化合物-3制备单体进料溶液。各种化合物的参考数字如下所示。分别用8.3g乳酸乙酯、3.5gγ-丁内酯和1.16g V-601制备引发剂进料溶液。在反应器中,将9.4g 70/30乳酸乙酯/GBL加热至80℃,并且然后以0.20mL/min滴加单体进料溶液持续240分钟,并以0.084mL/min滴加引发剂进料溶液持续90分钟。4小时后,将反应混合物以1℃/min冷却至室温,并且然后通过直接添加至1L(升)异丙醇中使聚合物沉淀。通过过滤收集聚合物并真空干燥,得到16.3g白色固体。分子量通过GPC相对于聚苯乙烯标准测定并发现是数均分子量(MN)=4510Da,重均分子量(Mw)=8050道尔顿,PDI(多分散指数)=1.8。
应当指出,表1中的所有聚合物均根据此通用合成方案制备。
表1
其中表1中的C1和C2是对比组合物,因为它们不含有化合物3。
表2
从表2中可以看出,实例聚合物在溶剂丙二醇单甲醚乙酸酯中具有良好的溶解度,而对比组合物不溶于溶剂丙二醇单甲醚乙酸酯。
实例3
进行所述实例以确定抗蚀剂组合物的抗蚀剂特性。配制品R1-R2(抗蚀剂组合物)和CR1-CR2(对比抗蚀剂组合物)以表3中所示的组分和量制备。在表3中,括号中的数字表示每种组分的重量比。在下表3描述了由C1、F1、P1、S1和S2表示的结构。
表3
使用TEL Lithius 300mm晶片轨道和ASML 1900i浸没式扫描仪以1.3NA(数值孔径)、0.86/0.61内/外σ和35Y极化的偶极子照明进行浸没式光刻。使用205℃/60sec固化,用AR40A底部抗反射涂层(BARC)涂覆用于光刻测试的晶片。使用175℃/60sec的固化,在AR40A层上涂覆的AR104 BARC。使用90℃/60sec的软烘烤在BARC叠层上涂覆的光致抗蚀剂。在焦点增加和剂量增加的情况下,将晶片暴露于55nm/110nm间距线/间距的图案并且然后在100℃/60sec下进行曝光后烘烤(PEB)。PEB之后,将晶片在0.26 N的TMAH水性显影剂中显影12sec,用蒸馏水冲洗,并且旋转干燥。
计量是在Hitachi CG4000 CD-SEM上进行的。线宽粗糙度(LWR)是通过从线宽测量的总共100个任意点的分布中获得一个3-σ值,然后使用MetroLER软件消除计量噪声来确定。
表4详细列出了55nm 1:1 LS(线间隔图案)下的曝光宽容度(EL)和线宽粗糙度(LWR)评估。
表4.
从表4中可以看出,与对比组合物(CR1和CR2)相比,所公开的组合物(R1和R2)的线宽粗糙度降低并且曝光宽容度增加。
Claims (10)
1.一种聚合物,包含:
第一重复单元和第二重复单元,其中所述第一重复单元包含酸不稳定基团并且其中所述第二重复单元衍生自式(1)的结构的聚合:
其中R1、R2和R3各自独立地是氢、卤素、取代或未取代的C1至C12烷基或C3至C12环烷基,其任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N-氧化物基团、磺酸酯基团、磺酰胺基团、或其组合、取代或未取代的C6至C14芳基、或C3至C12杂芳基,其中所述取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2-C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;
其中R1和R2一起任选地形成环;
其中Y选自羰基、磺酰基、或取代或未取代的亚甲基,
其中Y和R2一起任选地形成取代或未取代的4-7元单环或取代或未取代的9-12元双环,所述单环和双环任选地含有1、2、或3个选自N、O、和S的杂原子,其中每个环是饱和的、不饱和的或芳族的,并且其中每个环任选地含有醚基团、羰基、酯基团、碳酸酯基团、胺基团、酰胺基团、脲基团、硫酸酯基团、砜基团、亚砜基团、N-氧化物基团、磺酸酯基团、磺酰胺基团、或其组合,其中所述环上的取代是卤素、羟基、氰基、硝基、C1至C12烷基、C1至C12卤代烷基、C1至C12烷氧基、C3至C12环烷基、氨基、C2-C6烷酰基、甲酰氨基、取代或未取代的C6至C14芳基、或C3至C12杂芳基;并且其中R4和R5各自独立地是氢、卤素、取代或未取代的C1至C3烷基-其中所述取代是卤素;并且其中n=1-3。
3.如权利要求1或2中任一项所述的聚合物,其中所述第一重复单元是(甲基)丙烯酸酯单体或乙烯基芳族单体。
4.如权利要求1至3中任一项所述的聚合物,其中所述第一重复单元包含叔烷基酯。
5.如权利要求1至4中任一项所述的聚合物,其中所述第一重复单元包含缩醛基团或缩酮基团。
8.如权利要求1至7中任一项所述的聚合物,进一步包含第三重复单元,其含有内酯基团、磺内酯基团、和/或光酸产生剂基团中的一种。
9.一种光致抗蚀剂组合物,包含:
溶剂;
光酸产生剂;以及如权利要求1至8中任一项所述的聚合物。
10.一种图案形成方法,包括:
将如权利要求9所述的光致抗蚀剂组合物的层施加在基底上;
将所述光致抗蚀剂组合物层以图案方式暴露于活化辐射;以及
使所暴露的光致抗蚀剂组合物层显影以提供抗蚀剂浮雕图像。
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JP2020196872A (ja) | 2020-12-10 |
KR20200138006A (ko) | 2020-12-09 |
US20200377713A1 (en) | 2020-12-03 |
JP7160858B2 (ja) | 2022-10-25 |
TW202045569A (zh) | 2020-12-16 |
KR102389492B1 (ko) | 2022-04-21 |
TWI784272B (zh) | 2022-11-21 |
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