CN102630246B - 抗反射涂料组合物及其工艺方法 - Google Patents
抗反射涂料组合物及其工艺方法 Download PDFInfo
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- CN102630246B CN102630246B CN201080054063.5A CN201080054063A CN102630246B CN 102630246 B CN102630246 B CN 102630246B CN 201080054063 A CN201080054063 A CN 201080054063A CN 102630246 B CN102630246 B CN 102630246B
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- photoresist
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000006117 anti-reflective coating Substances 0.000 title claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 94
- 125000003118 aryl group Chemical group 0.000 claims abstract description 51
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 15
- -1 Methyl Chemical group 0.000 claims description 53
- 229920002120 photoresistant polymer Polymers 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000011159 matrix material Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- 238000003384 imaging method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 230000003667 anti-reflective effect Effects 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000004377 microelectronic Methods 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 229910052799 carbon Inorganic materials 0.000 description 30
- 238000000576 coating method Methods 0.000 description 29
- 239000011248 coating agent Substances 0.000 description 28
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 18
- 239000010703 silicon Substances 0.000 description 18
- 229910052710 silicon Inorganic materials 0.000 description 18
- 238000005530 etching Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical class O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
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- 239000000178 monomer Substances 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000004062 sedimentation Methods 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000007789 gas Substances 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
- 230000005855 radiation Effects 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000002242 deionisation method Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical class CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 125000002252 acyl group Chemical group 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
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- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
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- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical class O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
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- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical class CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- 150000003949 imides Chemical class 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000001393 microlithography Methods 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JBYLHICABMOUQN-UHFFFAOYSA-N 1-fluoroanthracene Chemical compound C1=CC=C2C=C3C(F)=CC=CC3=CC2=C1 JBYLHICABMOUQN-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
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- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3r)-3-hydroxybutyl] (3r)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 description 1
- HPFQPSQWZLFDMC-UHFFFAOYSA-N [2-nitro-6-(trifluoromethyl)phenyl]methyl 4-chlorobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1COS(=O)(=O)C1=CC=C(Cl)C=C1 HPFQPSQWZLFDMC-UHFFFAOYSA-N 0.000 description 1
- DATWRUPPMDEMOY-UHFFFAOYSA-N [2-nitro-6-(trifluoromethyl)phenyl]methyl 4-nitrobenzenesulfonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1C(F)(F)F DATWRUPPMDEMOY-UHFFFAOYSA-N 0.000 description 1
- GTZOZDOTOWNSJH-UHFFFAOYSA-N [O].CCCCCCC Chemical compound [O].CCCCCCC GTZOZDOTOWNSJH-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
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- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
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- 150000001503 aryl iodides Chemical class 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- NQIZDFMZAXUZCZ-UHFFFAOYSA-N carbifene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(=O)N(C)CCN(C)CCC1=CC=CC=C1 NQIZDFMZAXUZCZ-UHFFFAOYSA-N 0.000 description 1
- 229950003365 carbifene Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000005131 dialkylammonium group Chemical group 0.000 description 1
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Abstract
本发明涉及一种抗反射涂料组合物,含有交联剂和能够通过所述交联剂被交联的可交联聚合物,其中所述可交联聚合物含有结构式(1)所表示的单元,其中A是稠合的芳环,B具有结构式(2),其中R1是C1-C4烷基,R2是C1-C4烷基。本发明进一步涉及一种使用该组合物形成图像的方法。
Description
本发明涉及一种含有聚合物的吸收性硬质掩模抗反射涂料组合物,其中所述聚合物在聚合物的主链上含有至少一个苯基单元和至少一个取代或未取代的芳族稠合环,以及涉及一种使用所述抗反射涂料组合物形成图像的方法。所述方法尤其可用于使用深紫外和极紫外(UV)区域的辐射将光刻胶成像。
光刻胶组合物在微光刻(lithgraphy)方法中用于制造微型化电子部件,如在制造计算机芯片和集成电路中。通常地,在这些方法中,首先将一个光刻胶组合物薄涂层膜施涂到一个基体材料上,如用于制造集成电路的硅基晶片。接着将涂覆的基体进行烘烤以蒸发光刻胶组合物中的溶剂和将涂层固定在基体上。烘烤过的基体涂覆表面随后经受对辐射的成像式曝光。
该辐射曝光在涂覆表面的曝光区域引起化学变化。可见光、紫外(UV)光、电子束和X射线辐射能是如今微光刻方法中常用的辐射类型。在该成像式曝光之后,将涂覆的基体用显影剂溶液处理以溶解和除去光刻胶中辐射曝光或未曝光的区域。
半导体器件微型化趋势已经导致使用对越来越短的辐射波长敏感的新型光刻胶以及导致使用极其复杂的多级体系以克服该微型化所伴随而来的困难。
光刻术中的吸收性抗反射涂层和底层被用于消除光从高反射性基体的背反射导致的问题。背反射性的两个主要不利之处在于薄膜干涉效应和反射缺口效应(reflectivenotching)。薄膜干涉或驻波导致关键线宽尺寸变化,该尺寸变化是由光刻胶膜中总的光强度变化引起的,因为光刻胶厚度变化或者反射和入射的曝光辐射干涉会导致驻波效应,驻波效应使得穿过该厚度的辐射均匀性失真而引起的。在光刻胶在含有使光散射通过光刻胶膜的形貌特征的反射基体上被图案化时反射缺口效应变得严重,导致线宽变化,并且在极端情况下,形成光刻胶完全损失的区域。在光刻胶下面和反射基体上面涂覆的抗反射涂层在光刻胶的光刻性能上提供了显著的改进。典型地,将抗反射底涂层施涂于基体上,然后在该抗反射涂层顶部施涂光刻胶层。将该抗反射涂层固化以阻止该抗反射涂层和光刻胶之间发生混合。将光刻胶成像式曝光和显影。然后将曝光区域的抗反射涂层典型地用不同的蚀刻气体进行干蚀刻,光刻胶图案从而被转移到基体上。在新的光刻技术中使用多个抗反射层和底层。在其中光刻胶提供不了足够的耐干蚀刻性的情况下,优选的是起到硬质掩模作用和在基体蚀刻过程中有高耐蚀刻性的光刻胶底层或抗反射涂层,一种途径是将硅引入有机光刻胶层下面的层中。另外,在硅抗反射层下面添加另一高碳含量的抗反射层或掩模层,这用于改进成像过程的光刻性能。硅层可以是可旋涂的或通过化学气相沉积法沉积的。在其中用O2蚀刻的工艺方法中硅是高度耐蚀刻性的,并且通过在硅抗反射层下面提供具有高碳含量的有机掩模层,可以获得非常大的长宽比。这样,有机高碳掩模层可比它上面的光刻胶层或硅层厚得多。有机掩模层可以作为较厚的膜使用并且可以提供较好的掩蔽原始光刻胶的基体蚀刻。
本发明涉及一种新型的有机可旋涂抗反射涂料组合物或有机掩模底层,其具有高碳含量,和可作为多层之一的单独层在光刻胶层和基体之间使用。典型地,该新型组合物可用于在本质上耐蚀刻性的抗反射涂料层如硅抗反射涂层的下面形成一层。所述新型抗反射涂层中的高碳含量,也称之为碳硬质掩模底层,允许具有高的长宽比的高分辨图像转移。该新型组合物可用于使光刻胶成像,也可用于蚀刻基体。该新型组合物使得能够由光刻胶向基体进行良好的图像转移,还降低了反射和增强了图案转移。另外,在抗反射涂层和其上涂布的膜之间基本没有混合。该抗反射涂层还具有良好的溶液稳定性和形成具有良好涂层质量的膜,后者对于光刻术是特别有利的。
发明概述
本发明涉及一种抗反射涂料组合物,其包含交联剂和能够通过所述交联剂被交联的可交联聚合物,其中所述可交联聚合物含有结构式(1)所表示的单元:
其中A是稠合的芳环,B具有结构式(2),
其中R1是C1-C4烷基,R2是C1-C4烷基。
本发明进一步涉及一种使用该组合物形成图像的方法。
附图简述
图1说明了成像的方法。
发明详述
本发明涉及一种吸收性抗反射涂料组合物,其包含交联剂和能够通过所述交联剂被交联的可交联聚合物,其中所述聚合物在聚合物的主链上含有至少一个带苯基的单元和至少一个稠合的芳族单元。本发明还涉及一种将涂布在该新型抗反射涂料层上的光刻胶层成像的方法。
本发明的新型抗反射组合物包含能够交联的具有高碳含量的新型聚合物,使得由该组合物形成的涂层交联后变得不溶于涂布于其上的材料的溶剂中。该新型的涂料组合物能够自交联或可以另外包含能够与该聚合物交联的交联化合物。该组合物可以另外包含其他添加剂,如有机酸、酯、热致酸生成剂、光致酸生成剂、表面活性剂、其他高碳含量聚合物等。该组合物可以包含另外的聚合物,尤其是具有高碳含量的那些。将该新型组合物的固体组分溶解于包含一种或多种有机溶剂的有机涂料溶剂组合物中。该新型聚合物在该有机涂料溶剂中是可溶的。
该新型组合物的聚合物在聚合物主链中包含至少一个稠合的芳族结构部分单元和至少一个带有苯基结构部分的单元。该聚合物可由结构式1表示:
其中A是稠合的芳环结构部分,B具有结构式(2),
其中R1是C1-C4烷基,R2是C1-C4烷基。该稠合的芳族结构部分含有2个或更多个稠合在一起的芳族单元。该稠合的芳族结构部分可以含有2-8个芳环或2-6个芳环或3-5个芳环或3-4个芳环。该稠合的芳环可以含有3个芳环。该稠合的芳环可以是蒽基。
该新型聚合物可以由包含苯基结构部分的单体与包含稠合的芳族基团的单体在酸催化剂存在下缩合反应获得。聚合物中稠合的芳族结构部分包含取代的或未取代的稠合芳环。聚合物的稠合芳环可以包含2-8元芳环。该稠合芳族结构部分的例子有下面结构式3-14:
尽管所述单元可以如结构式3-14所示,但稠合的环还可以在芳香结构中的任何位点形成聚合物主链并且连接位点可以在聚合物中变化。稠合的环结构可以具有两个以上连接点,形成支化的低聚体或支化的聚合物。在该聚合物的一个具体实施方案中,稠合的芳族单元连接到另一个芳族碳结构部分或另一个稠合的芳族单元上。可以形成稠合的芳族单元嵌段和所述嵌段通过饱和的脂肪族碳单元如亚甲基被分隔开。
聚合物的稠合芳环可以是未取代的或用一个或多个有机组分取代的,所述有机组分如烷基、取代的烷基、芳基、取代的芳基、烷芳基和卤代烷基、羟基、氨基、氨基烷基、烷氧基,如甲基、氨基甲基、溴代甲基和氯代甲基。可以存在最多4个取代基。芳环上的取代基可有助于聚合物在涂料溶剂中的溶解性。稠合的芳族结构上的一些取代基在固化过程中也可被热解,使得它们可以不残留在固化的涂层中并从而得到可用于蚀刻加工工艺中的高碳含量膜。
该聚合物可以包含不止一类这里所述的稠合芳族结构。在一个实施方案中,稠合的芳族结构部分是未取代的。在一个实施方案中,稠合的芳族结构部分不含羟基或烷氧基。在另一个实施方案中,A的稠合的芳族结构部分和B的苯基是未取代的,就是仅用氢取代。
除了稠合环单元,该新型抗反射涂层的聚合物进一步包含至少一个单元B,如结构式1所示,单元B含有苯基。单元B可衍生自含2个不饱和基团的单体,如烷基取代的或未取代的二乙烯基苯。聚合物包含单元-(A)-和-(B)-,其中A是前述的任何稠合芳族单元,其可以是线性的或支化的、取代的或未取代的,其中B是苯基,通过饱和的碳连接在A上,如结构式2所示。
芳基或芳族基团含有6-24个碳原子,包括苯基、甲苯基、二甲苯基、萘基、蒽基、联苯基、二苯基、三苯基等。这些芳基可以进一步被任何适合的取代基取代,例如上述的烷基、烷氧基、酰基或芳基。类似地,本发明中可以按需要使用适合的多价芳基。二价芳基代表性的例子包括亚苯基、亚二甲苯基、亚萘基、亚联苯基等。烷氧基指的是具有1-20个碳原子的直链或支化链的烷氧基,包括,例如甲氧基、乙氧基、正-丙氧基、异丙氧基、正-丁氧基、异丁氧基、叔-丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基、4-甲基己氧基、2-丙基庚氧基和2-乙基辛氧基。芳烷基指的是带有连接的取代基的芳基。所述取代基可以是任何取代基如烷基、烷氧基、酰基等。具有7-24个碳原子的一价芳烷基的例子包括苯甲基、苯乙基、二苯甲基、1,1-或1,2-二苯基乙基、1,1-,1,2-,2,2-或1,3-二苯基丙基等。这里所述的具有所需价的取代芳烷基的适当结合可以用作多价芳烷基。
在一个实施方案中,该新型的聚合物不含任何脂肪族环基团或多环基团,如环己基、金刚烷基、降冰片基等。在另一个实施方案中,该新型的聚合物不含任何脂肪族环基团或多环基团、羟基或烷氧基。在一个实施方案中,组合物中的聚合物不包含脂肪族多环基团,如环己基、金刚烷基、降冰片基等。
本发明新型组合物的聚合物可以通过a)和b)在酸催化剂存在下反应来合成:a)至少一种芳族化合物,其含有2个或更多个能够亲电取代的稠合芳环,使得所述稠合环形成聚合物主链;b)至少一种带有可以形成碳正离子的两个活性位点的芳族单元。该芳族化合物可以选自提供所需的芳族单元、更具体而言是上面所示的结构或等价物的单体,并可以进一步选自化合物如蒽、菲、芘、氟代蒽、三亚苯基六苯并苯(coronenetriphenylene)、蒽甲醇、甲基甲氧基蒽(anthracenemethylmethoxy)等。稠合芳环提供至少2个反应性位点,该位点是用于亲电取代的位点。
形成新型聚合物中的单元B使用的单体包含带有两个反应性位点的苯基单元,所述位点在酸存在下能够形成碳正离子,所述单体可选自化合物如二乙烯基苯。反应在强酸如磺酸存在下被催化。可以使用任何磺酸,其例子是三氟甲磺酸、九氟丁磺酸、双全氟烷基酰亚胺、三全氟烷基碳化物或其他强的非亲核性酸。反应可以使用或不用溶剂进行。如果使用溶剂,则可以使用能够溶解该固体组分的任何溶剂,尤其是对强酸为非反应性的溶剂;可以使用溶剂如氯仿、双(2-甲氧基乙基醚)、硝基苯、二氯甲烷和二甘醇二甲醚、三甘醇二甲醚、二(乙二醇)二甲醚、二(乙二醇)二乙醚、二(丙二醇)二甲醚、二(丙二醇)二乙醚、丙二醇单甲基醚乙酸酯(PGMEA)、丙二醇单甲基醚(PGME)。反应可以在适合的温度下混合合适长度的时间,直到聚合物形成。反应时间范围可以为大约3小时-大约24小时,以及反应温度范围可以为大约80℃-大约180℃。分离聚合物并在适当的溶剂如甲醇、己烷、庚烷中通过沉淀和洗涤纯化。可以将该新型的聚合物分级以得到具有所需分子量的级分。将聚合物溶解在溶剂例如四氢呋喃(THF)中;向该溶液中加入非溶剂如烷烃;形成沉淀并进行过滤。分级过程可以在室温下进行。聚合物可以进一步被纯化。典型地,除去低分子量部分。可以使用之前已知的反应、分离和纯化聚合物的技术。聚合物的重均分子量范围可以为大约1200-大约5,000,或大约1300-大约3,000或大约1,500-大约2,600。
聚合物的折光指数n(折光指数)和k(吸收度)范围在使用的曝光波长如193nm下可以为折光指数大约1.3-大约2.0和吸收度为大约0.05-大约1.0。聚合物或组合物的碳含量通过固体组合物的元素分析进行测定。可以在基体上形成涂层和将膜干燥之后测量组合物或聚合物的碳含量。对固体涂层或干燥的聚合物进行元素分析提供的碳含量以重量%计。通过元素分子测量的、聚合物或组合物在交联后的碳含量大于80重量%,或大于85重量%,或大于90重量%。在一个实施方案中聚合物交联后的碳含量范围为80-95重量%。
本发明新型组合物的聚合物可以具有如结构式(15)所示的结构单元,其中R1和R2如前面所述。
本发明的新型组合物包含聚合物和可以进一步包含交联剂。典型地,交联剂是可以充当亲电子试剂和可以单独地或在酸存在下形成碳正离子的化合物。这样的含有基团如醇、醚、酯、烯烃、甲氧基甲基氨基、甲氧基甲基苯基的化合物和含有多个亲电子位点的其他分子能够与该聚合物交联。可以使用聚合物交联剂,如甘脲和三聚氰胺等的聚合物。可以是交联剂的化合物的例子是1,3金刚烷二醇、1,3,5金刚烷三醇、多官能反应性苄基化合物、结构(16)的四甲氧基甲基双酚(TMOM-BP)、氨基塑料交联剂、甘脲、聚氰胺树脂、粉末连接剂(Powderlinks)等。
该含有聚合物的新型组合物也可以包含酸生成剂和任选地包含交联剂。酸生成剂可以是加热时能够生成强酸的热致酸生成剂。本发明使用的热致酸生成剂(TAG)可以是在加热时生成酸的任何一种或多种,所生成的酸可与聚合物反应和使本发明的聚合物交联,特别优选的是强酸如磺酸。优选地,该热致酸生成剂在90°C以上,更优选在120°C以上,甚至更优选在150°C以上被活化。热致酸生成剂的例子是不含金属的锍盐和碘鎓盐,如非亲核性强酸的三芳基锍盐、二烷基芳基锍盐和二芳基烷基锍盐,非亲核性强酸的烷基芳基碘鎓盐、二芳基碘鎓盐;以及非亲核性强酸的铵盐、烷基铵盐、二烷基铵盐、三烷基铵盐、四烷基铵盐。而且,共价的热致酸生成剂也被视作可用的添加剂例如烷基或芳基磺酸的2-硝基苄基酯和热分解产生游离磺酸的其他磺酸的酯类。例子是二芳基碘鎓全氟烷基磺酸盐、二芳基碘鎓三(氟烷基磺酰基)甲基化物、二芳基碘鎓双(氟烷基磺酰基)甲基化物、二芳基碘鎓双(氟烷基磺酰基)酰亚胺、二芳基碘鎓季铵全氟烷基磺酸酯。不稳定的酯的例子:甲苯磺酸2-硝基苄基酯、甲苯磺酸2,4-二硝基苄基酯、甲苯磺酸2,6-二硝基苄基酯、甲苯磺酸4-硝基苄基酯;苯磺酸酯类如4-氯苯磺酸2-三氟甲基-6-硝基苄基酯、4-硝基苯磺酸2-三氟甲基-6-硝基苄基酯;酚磺酸酯类如4-甲氧基苯磺酸苯基酯;三(氟烷基磺酰基)甲基化季铵、和双(氟烷基磺酰基)酰亚胺四芳烷基铵、有机酸的烷基铵盐,如10-樟脑磺酸的三乙基铵盐。各种芳族(蒽、萘或苯衍生物)磺酸胺盐都可用作TAG,包括U.S.专利第3,474,054、4,200,729、4,251,665和5,187,019号中公开的那些。优选TAG在170-220°C之间具有非常低的挥发性。TAG的例子是KingIndustries公司以Nacure和CDX的名字所售的那些。该类TAG是Nacure5225和CDX-2168E,其为在丙二醇甲基醚中的活性为25-30%的十二烷基苯磺酸胺盐,是美国康涅狄格州诺沃克(06852)的KingIndustries公司供应的。
该新型的组合物可进一步含有至少一种已知的光致酸生成剂,其例子非限制性地有鎓盐、磺酸酯化合物、硝基苄基酯、三嗪等。优选的光致酸生成剂是鎓盐和羟基酰亚胺的磺酸酯类、具体是二苯基碘鎓盐、三苯基锍盐、二烷基碘鎓盐、三烷基锍盐、及它们的混合物。这些光致酸生成剂不是必须光解的而是热分解形成酸。
本发明的抗反射涂料组合物可以含有占该组合物中总固体1重量%-大约30重量%的新型稠合芳族聚合物,优选4重量%-大约15重量%。当组合物中使用交联剂时,交联剂可以大约1重量%-大约30重量%总固体存在。可以大约0.1-大约10重量%抗反射涂料组合物总固体,优选0.3-5重量%固体,更优选0.5-2.5重量%固体引入热致酸生成剂。
该新型组合物可以进一步包含第二聚合物。所述第二聚合物可以是也具有大于75重量%碳含量,或大于80重量%碳含量的聚合物。所述第二聚合物可以包含如这里所述的含稠合芳环的单元A、苯基结构部分B和选自具有两个以上芳环的取代稠合芳环的第三单元。第三单元可以选自用羟基取代的稠合芳族单元。第三单元可以选自羟基蒽基结构部分、羟基苯基结构部分、羟基萘基结构部分、羟基芘基结构部分、C1-C4烷氧基蒽基结构部分、C1-C4烷基苯基结构部分、C1-C4烷基萘基结构部分、C1-C4烷基芘基结构部分等。第三单元可以选自羟基苯基、羟基萘基、羟基菲基、羟基蒽基等。第三单元可以是羟基萘基。可以1重量%-20重量%的聚合物在组合物中的总浓度,或1%-10重量%的聚合物总浓度将第二聚合物加入到组合物中。在一个实施方案中,第二聚合物不含任何脂肪族环状多环基团。在另一个实施方案中,第二聚合物不含任何脂肪族环状多环基团和第三单元是羟基萘基。
在一个实施方案中,所述新型的组合物包含新型聚合物、这里所述的第二聚合物、交联剂、热致酸生成剂、任选的表面活性剂和溶剂。
将抗反射涂料组合物的固体组分与溶解该抗反射涂层的固体组分的溶剂或溶剂混合物进行混合。对该抗反射涂料组合物适合的溶剂可以包括,例如,二醇醚衍生物如乙基溶纤剂、甲基溶纤剂、丙二醇单甲基醚、二甘醇单甲基醚、二甘醇单乙基醚、二丙二醇二甲基醚、丙二醇正丙基醚、或二甘醇二甲基醚;二醇醚酯衍生物如乙基溶纤剂乙酸酯、甲基溶纤剂乙酸酯、或丙二醇单甲基醚乙酸酯;羧酸酯类如乙酸乙酯、乙酸正丁酯和乙酸戊酯;二元酸的羧酸酯如草酸二乙酯(diethyloxylate)和丙二酸二乙酯;二醇的二羧酸酯类如乙二醇二乙酸酯和丙二醇二乙酸酯;和羟基羧酸酯如乳酸甲酯、乳酸乙酯、乙醇酸乙酯和3-羟基丙酸乙基酯;酮酯如丙酮酸甲酯或丙酮酸乙酯;烷氧基羧酸酯如3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-羟基-2-甲基丙酸乙酯、或甲基乙氧基丙酸酯;酮衍生物如甲基乙基酮、乙酰丙酮、环戊酮、环己酮或2-庚酮;酮醚衍生物如二丙酮醇甲基醚;酮醇衍生物如丙酮醇或二丙酮醇;内酯如丁内酯;酰胺衍生物如二甲基乙酰胺或二甲基甲酰胺、茴香醚、以及它们的混合物。
该抗反射涂料组合物可包含其他组分以提高涂层性能,例如单体染料、低级醇(C1-C6醇)、表面流平剂、附着促进剂、防沫剂等。
由于该抗反射膜被涂覆到基体顶部并也经受干蚀刻,可以预想该膜具有足够低的金属离子水平和足够的纯度使得半导体器件的性能不受不利影响。可以采用如使聚合物溶液穿过离子交换柱、过滤和萃取过程等处理方法以降低金属离子浓度和减少颗粒。
由偏振测量仪所得的该新型组合物在曝光波长下的吸收参数(k)的范围是大约0.05-大约1.0,优选为大约0.1-大约0.8。在一个实施方案中,该组合物在曝光波长下具有的k值范围是大约0.2-大约0.5。将该抗反射涂层的折光指数(n)也进行优化,其范围可以是大约1.3-大约2.0,优选1.5-大约1.8。n和k值可以用偏振仪计算,如J.A.WoollamWVASEVU-32TM偏振仪。k和n最佳范围的确切值取决于使用的曝光波长和应用类型。典型地,对于193nm来说优选的k范围是大约0.05-大约0.75,对于248nm来说优选的k范围是大约0.15-大约0.8。
通过由该组合物制备的干膜进行元素分析测得的该新型抗反射涂料组合物的碳含量为大于80重量%或大于85重量%。即使在来自该新型组合物的膜被加热到高达400℃的温度长达120秒,由该组合物得到的膜的碳含量也保持在80重量%的水平或大于80重量%。
用本领域熟练技术人员公知的技术,如浸涂、旋涂或喷涂将该抗反射涂料组合物涂布到基体上。该抗反射涂层的膜厚度范围是大约15nm-大约400nm。将涂层进一步在热板上或对流炉中加热足够长的时间以除去任何残余的溶剂和引起交联,从而使该抗反射涂层不能溶解以防止该抗反射涂层和要涂覆在它上面的层之间发生混合。优选的温度范围是大约90℃-大约280℃。
可以将其他类型的抗反射涂层涂覆到本发明的图层之上。典型地,使用具有高的耐氧蚀刻性的抗反射涂层,如包含硅基团如硅氧烷、官能化的硅氧烷、倍半硅氧烷、或其他降低蚀刻速率的结构部分等的涂层,以便使得该涂层可以充当图案转移的硬质掩模。硅涂层可以旋涂或化学气相沉积。在一个实施方案中,基体用本发明的新型组合物的第一层膜涂覆,将另一含硅的抗反射涂料的第二涂层涂覆在第一层膜上。第二涂层可以具有大约0.05-0.5的吸收度值(k)。然后将光刻胶膜涂覆到第二涂层上。成像过程例举于附图1中。
将光刻胶膜涂覆到最上层抗反射涂层的顶部并进行烘烤以基本除去光刻胶溶剂。在涂覆步骤之后可以用本领域公知的方法施以边胶清洗剂以清洁基体的边。
上面形成有抗反射图层的基体可以是半导体工业中通常使用的那些中的任一种。适合的基体包括,并不限制于,低介电常数材料、硅、涂覆有金属表面的硅基体、铜涂覆的硅晶片、铜、铝、聚合物树脂、二氧化硅、金属、掺杂的二氧化硅、氮化硅、钽、聚硅氧烷、陶瓷、铝/铜混合物;砷化镓和其他第III/V族化合物。基体可以包含任意数目的由上述材料制成的层。
光刻胶可以是半导体工业中使用的任何类型,条件是光刻胶和抗反射涂层中的光活性化合物在成像方法中使用的曝光波长上是基本吸收的。
迄今为止,有几个在微型化上提供了显著提高的主要的深紫外(uv)曝光技术,和248nm、193nm、157和13.5nm的这些辐射。用于248nm的光刻胶典型地基于取代的聚羟基苯乙烯及其共聚物/鎓盐,如US4,491,628和US5,350,660所描述的那些。另一方面,在193nm和157nm曝光的光刻胶要求非芳族聚合物,因为在此波长下芳族聚合物是不透明的。US5,843,624和US6,866,984公开了可用于193nm曝光的光刻胶。通常,含脂环烃的聚合物用于200nm之下曝光的光刻胶。脂环烃可由于多种原因引入聚合物中,主要因为它们具有相对高的碳氢比,这提高了耐蚀刻性,它们也提供了在低波长下的透明度,并且它们具有相对高的玻璃化转变温度。US5,843,624公开了通过马来酐和不饱和环状单体自由基聚合得到的光刻胶聚合物。可以使用任何已知类型的193nm光刻胶,如US6,447,980和US6,723,488中所描述的那些,这里引入作为参考。在157nm处敏感和基于带有氟代醇侧基的氟化聚合物的两种基本类型的光刻胶已知在该波长基本是透明的。一类157nm的氟代醇光刻胶是由含基团如氟代降冰片烯的聚合物衍生的,用金属催化或自由基聚合均聚或与其他透明单体如四氟乙烯共聚(US6,790,587和US6,849,377)。通常,由于它们具有高的脂环含量,这些材料除了具有良好的耐等离子蚀刻性之外还给出了较高的吸收度。最近,描述了一类157nm氟代醇聚合物,其中聚合物主链衍生自不对称二烯如1,1,2,3,3-五氟-4-三氟甲基-4-羟基-1,6-庚二烯的环化聚合(US6,818,258)或氟代二烯与烯烃共聚合(US6,916,590)。这些材料在157nm给出了可以接受的吸收度,但由于与氟代降冰片烯聚合物相比它们较低的脂环含量,所以具有较低的耐等离子蚀刻性。这两类聚合物常可混合以提供第一类聚合物的高耐蚀刻性和第二类聚合物在157nm的高透明度之间的平衡。也可以使用吸收13.5nm的极紫外辐射(EUV)的光刻胶,这是本领域已知的。该新型涂层也可以用于纳米压印和电子束光刻术中。
涂覆工艺后,用掩膜将光刻胶成像式曝光。曝光可以用典型的曝光设备进行。曝光波长源的例子有248nm和193nm,尽管任何源都可以使用。然后将曝光的光刻胶在水性显影剂中显影以除去处理过的光刻胶。显影剂优选是含例如四甲基氢氧化铵(TMAH)的碱性水溶液。显影剂的例子是0.26N四甲基氢氧化铵(TMAH)水溶液。显影剂可进一步包含表面活性剂。在显影之前和曝光之后可以将任选的加热步骤引入所述工艺过程中。
涂覆和成像光刻胶的方法是本领域技术人员所公知的,并进行优化用于所用光刻胶的具体类型。然后,图案化的基体可以用蚀刻气体或蚀刻气体混合物在合适的蚀刻室内进行干蚀刻,以除去抗反射膜或多层抗反射图层的曝光部分,残余的光刻胶起到蚀刻掩膜的作用。本领域中已知各种蚀刻气体用于蚀刻有机抗反射涂层,如含O2、CF4、CHF3、Cl2、HBr、SO2、CO等的那些。
无论如何,上面参考的每一篇文献都全文参考引入。下面具体的实施例将对制备和利用本发明组合物的方法提供详细的示例性说明。然而这些实施例并不意欲以任何方式限制或限定本发明的范围,不应解释为提供了为实践本发明必须专有地使用的条件、参数或值。
实施例
在J.A.WoollamVASE32偏光仪上测量下面实施例中的碳硬质掩模抗反射涂层的折光指数(n)和吸收度(k)值。
在凝胶渗透色谱仪上测量聚合物的分子量。
实施例1.
将9-蒽甲醇(52.06g~0.25mol)、二乙烯基苯(16.3g~0.125mol)装入装备有搅拌器、冷凝器、温度表和氮气清扫口(sweep)的2升四颈园底烧瓶中。加入213g二(乙二醇)二甲醚(二甘醇二甲醚),和60g环戊基甲基醚(CPME),在氮气下将其混合10分钟。加入2.05g三氟甲基磺酸并混合10分钟。将烧瓶加热到140℃并回流3小时。反应后将烧瓶冷却,加入500mlCPME。将反应混合物转移到带有底部出口阀的5L烧瓶中。加入300mL去离子(DI)水,混合并使其静置以形成分离的水层。将聚合物溶液与5L己烷混合。将沉淀过滤、用己烷洗涤并真空干燥。将粗聚合物(46.0g)溶解于四氢呋喃(THF)(400ml)。将该溶液加入到4升己烷中,形成沉淀。将聚合物沉淀过滤、用己烷洗涤和真空干燥,得到54%的产率,GPCMw为1898和多分散性(Pd)为1.77。所获得的聚合物元素分析以重量计为碳-92.29%,氢-5.91%,氧-1.8%。
实施例2.
将7.0g实施例1的聚合物、0.70g四甲氧基甲基-双酚(TMOM-BP)、2.80g十二烷基苯磺酸与盐形式的三乙基胺在环己酮/PGMEA(70/30)中的10%溶液和89.5g环己酮/PGMEA(70/30)进行混合。完全混合后,将该配制剂通过0.04μm的过滤器过滤。
实施例3.
以1500rpm将来自实施例2的过滤过的溶液旋涂到8”的硅晶片上。将涂覆过的晶片在230℃下在热板上烘烤60秒。将薄的涂覆材料用刀片从晶片表面刮下并进行元素分析。结果示于表1中。以1500rpm用实施例2的过滤的溶液旋涂另一硅晶片并将涂覆过的晶片在400℃下烘烤120秒。将烘烤过的材料用刀片从晶片表面刮下并进行元素分析。结果示于表1中。
表1
实施例2的组合物 | 碳(%) | 氢(%) | 氧(%) |
在230℃下烘烤60秒 | 91.52 | 6.03 | 2.45 |
在400℃下烘烤120秒 | 83.41 | 3.48 | 13.11 |
对比实施例1:
用二羟甲基苯代替二乙烯基苯重复实施例2。得到的聚合物给出了60%的产率,GPCMw为1374和Pd为1.79,元素分析以重量计:碳-90.60%,氢-5.15,氧-2.53%。
对比实施例2:
用对比实施例1的聚合物重复实施例2。
对比实施例3:
用对比实施例2的材料重复实施例3,结果如下表2中所示。
表2
对比实施例2的样品 | 碳(%) | 氢(%) | 氧(%) |
在230℃下烘烤60秒 | 91.62 | 5.55 | 2.83 |
在400℃下烘烤120秒 | 78.33 | 3.17 | 18.5 |
与实施例2的组合物相比,对比组合物2在加热到400℃后给出了较低的碳含量,其中烘烤后较高的碳含量、尤其是大于80重量%是所需的。
对比实施例4:
用二甲氧基甲基苯代替二乙烯基苯重复实施例1。
得到的聚合物给出的Mw为1374,Pd为1.79。元素分析显示所述聚合物含有碳-90.60%重量、氢-5.15%重量和氧-4.25%重量。
对比实施例5:
用对比实施例4的聚合物重复对比实施例2。
对比实施例6:用对比实施例5的溶液重复对比实施例3,结果示于下表3中。
表3
对比实施例5的样品 | C (%) | H (%) | O (%) |
在230℃下烘烤60秒 | 91.02 | 5.45 | 3.53 |
在400℃下烘烤120秒 | 77.63 | 3.27 | 19.1 |
与实施例2的组合物相比,对比组合物5在加热到400℃后给出了较低的碳含量,其中烘烤后较高的碳含量是所需的。
实施例8.
n和k的测量:用环己酮将实施例2的配制剂调节到1.25重量%固体并将混合物混合直到所有材料都变得可溶。将该均匀的溶液通过0.2μm的膜滤器过滤。以2000rpm将此过滤过的溶液旋涂到4”硅晶片上。将该涂覆的晶片在热板上在230℃下烘烤60秒。然后,用J.A.Woollam公司制造的VASE偏光仪测量n和k值。用于193nm辐射的膜的光学常数n和k为n=1.47,k=0.56。
实施例9.
将实施例2的均匀溶液用0.2μm的膜滤器过滤。以1500rpm将此过滤的溶液旋涂到6”硅晶片上。将涂覆的晶片在热板上在230℃下烘烤60秒。烘烤后,将该晶片冷却到室温并部分浸入PGME中30秒。该涂层无缺陷。检查该晶片浸入和未浸入区域的膜厚度的变化。由于烘烤膜有效的交联,在浸入的区域没有观察到膜损失。
实施例10.
使用PerkinElmerTGA7在400℃于空气下对实施例1的聚合物进行非等温热重分析,TGA,测量120分钟,结果显示聚合物的重量损失为2.27%,这样显示了该新型聚合物具有非常小的重量损失。
实施例11.
在NE-5000N(ULVAC)上采用表4中列出的氧化性(富氧)的和富含碳氟化合物的蚀刻条件,测量该抗反射涂层的无图案(blanket)蚀刻速率。实施例2和对比实施例2的配制剂的大约250nm厚度的抗反射涂层膜,分别被涂覆到8”的硅晶片上,在230°C下烘烤1分钟。在Nanospec8000上用通过膜VASE分析得到的柯西(cauchy)材料依赖常数进行单独的膜厚测量程序,蚀刻20秒之前或之后,进行5个点检查。然后通过膜厚度差除以蚀刻时间计算蚀刻速率。蚀刻速率掩蔽电位(maskingpotential)示于表5和表6中的蚀刻速率数据中。对比实施例2给出了比实施例2高的蚀刻速率,其中较低的蚀刻速率是所希望的。
表4:用于无图案蚀刻速率研究的蚀刻条件
蚀刻条件 | 氧化性条件 | 碳氟化合物条件 |
气体 | Cl2/O2/Ar,24/6/25SCCM | CF4/O2/Ar,50/20/150SCCM |
工艺压力 | 1.6Pa | 5Pa |
板温度:20°C;RF功率:500W,50W偏压
表5:使用氧化性条件的蚀刻速率
表6:使用碳氟化合物条件的蚀刻速率
实施例12.
以1500rpm用实施例2的组合物涂覆8英寸的晶片得到200nm的膜厚度,在350℃下烘烤120秒。在其顶部涂布含硅的底部抗反射涂层,ArFS24H(硅抗反射涂层,由新泽西萨默维尔的MaterialsUSA公司获得),得到31nm的膜厚度,在230℃下烘烤60秒。然后将光刻胶(193nm光刻胶,由新泽西萨默维尔的MaterialsUSA公司获得)涂到抗反射涂层的顶部,得到125nm的膜厚度,在100°C下轻柔烘烤60秒。用193nm曝光工具(NikonNSR-306D:NA=0.85,偶极:0.82/0.43)使光刻胶成像式曝光,在110°C下烘烤60秒,然后在0.26N的四甲基氢氧化铵(TMAH)水溶液中显影。然后在扫描电子显微镜下观察线和空间图案,分析具有50nm临界尺寸、1:2间距(Pitch)的图案。该光刻胶具有48.0mJ/cm2的光敏性。该光刻胶图案具有良好的图案特征,在光刻胶图案底部没有脚子或浮渣。该光刻胶图案没有驻波,从基体到图案显示最小的反射性。光刻胶图案可以用前述的蚀刻条件或其他最合适的条件被转移到基体上。用CF4气体蚀刻图案样品,之后用O2除去所有残余的有机材料。然后用CF4气体蚀刻基体。用扫描电子显微镜(SEM)观察图案的横截面。
实施例13.
将9-蒽甲醇(166.6g~0.80mol)和二乙烯基苯(16.3g~0.125mol)加入到装备有搅拌器、冷凝器、温度表和氮气清扫口的2升四颈园底烧瓶中。加入500g二(乙二醇)二甲醚(二甘醇二甲醚),和150g环戊基甲基醚,在氮气下将其混合10分钟。加入6.5g三氟甲基磺酸并混合10分钟。将烧瓶加热到140℃并回流3小时。反应后将烧瓶冷却,加入500mlCPME。加入400mL去离子(DI)水,混合并使其静置以形成分离的水层。除去水层。将聚合物溶液与8L己烷混合。将沉淀过滤、用己烷洗涤并真空干燥。将粗聚合物(154g)溶解于四氢呋喃(1386g)中。在搅拌下向该溶液中缓慢加入824g己烷,形成沉淀。将沉淀过滤和用己烷洗涤,真空干燥得到产率为38%的分级聚合物;GPCMw为2162,多分散性(Pd)为1.83。
实施例14.
用实施例13的聚合物重复实施例2。
实施例15.
用实施例14的组合物重复实施例3,结果示于表8中。
表8
实施例14的组合物 | 碳(%) | 氢(%) | 氧(%) |
在230℃下烘烤60秒 | 92.33 | 5.77 | 1.9 |
在400℃下烘烤120秒 | 83.78 | 3.48 | 12.74 |
实施例16.
将9-蒽甲醇(26g~0.125mol)、二乙烯基苯(16.25g~0.125mol)和1-萘酚(18g,0.125mol)加入到装备有搅拌器、冷凝器、温度表和氮气清扫口的2升四颈园底烧瓶中。加入210g二甘醇二甲醚和60g环戊基甲基醚,在氮气下将其混合10分钟。加入1.81g三氟甲基磺酸并混合10分钟。将烧瓶加热到140℃并回流3小时。反应后,将烧瓶冷却至大约80℃,加入500mlCPME和1.3g三乙基胺。将反应混合物转移到带有底部出口阀的5L烧瓶中。加入300mLDI水,混合并静置,形成分离的水层。将聚合物溶液加入到3L己烷中。将聚合物沉淀过滤、用己烷洗涤并真空干燥。将聚合物(70.0g)溶解于THF(200ml)中。将该溶液加入到3.0升叔丁基甲基醚中,形成沉淀。将沉淀过滤、用己烷洗涤和真空干燥。聚合物产率为33%,GPCMw为5561,Pd为2.04,元素分析:碳-87.11%、氢-5.95%、氧-6.95。
实施例17
将7.35g实施例13的分级聚合物加入到瓶中,加入1.84g实施例16的聚合物,加入0.37gTMOM-BP,以在环己酮/PGMEA(70/30)中的10%溶液的形式加入2.94gDBSA,以在70/30环己酮/PGMEA中1%的形式加入0.50gFC-4430(由明尼苏达州的3M公司可得)和加入86.9g环己酮/PGMEA(70/30)。混合后,将该配制剂通过0.04μm的过滤器过滤。将此过滤过的溶液以1500rpm旋涂到8”的硅晶片上。将涂覆过的晶片在热板上在230℃下烘烤60秒并检测缺陷。该涂层完全没有缺陷。
对比实施例18:
在不使用实施例17的聚合物的情况下重复实施例17,检查后发现涂层有涂层缺陷。
Claims (15)
1.一种抗反射涂料组合物,含有交联剂和能够通过所述交联剂被交联的可交联聚合物,其中所述可交联聚合物含有结构式(1)所表示的单元:
其中A是稠合芳环,所述稠合芳环包含3-5个稠合的芳环且其进一步是未取代的或用一个或多个有机组分取代,所述有机组分选自烷基、取代的烷基、芳基、取代的芳基、烷芳基、羟基、氨基、和氨基烷基,B具有结构式(2),
其中R1是C1-C4烷基,R2是C1-C4烷基且其中所述组合物进一步包含酸生成剂,
其中所述组合物中的聚合物不含脂肪族多环结构部分。
2.如权利要求1所述的组合物,其中所述取代的烷基为卤代烷基。
3.如权利要求1所述的组合物,其中R1是甲基和R2是甲基。
4.如权利要求1所述的组合物,其中所述稠合芳环具有3或4个芳环。
5.如权利要求1-4中任一项所述的组合物,其中所述酸生成剂是热致酸生成剂。
6.如权利要求1-4中任一项所述的组合物,其中所述聚合物具有1,200-10,000的重均分子量。
7.如权利要求1-4中任一项所述的组合物,进一步含有表面活性剂。
8.如权利要求1-4中任一项所述的组合物,进一步含有第二聚合物,其中所述第二聚合物含有羟基芳族结构部分。
9.如权利要求1-4中任一项所述的组合物,其中所述组合物具有的碳含量大于80重量%固体含量。
10.如权利要求1-4中任一项所述的组合物,其中结构式(1)中的A选自如下结构:
11.一种制造微电子器件的方法,包括:
a)为基体提供来自权利要求1-10中任一项所述的抗反射涂料组合物的第一抗反射涂料层;
b)任选地,在所述第一抗反射涂料层之上提供至少第二抗反射涂料层;
c)在所述抗反射涂料层上涂布光刻胶层;
d)将所述光刻胶层成像式曝光;
e)用碱性显影水溶液将所述光刻胶层显影。
12.如权利要求11所述的方法,其中所述第一抗反射涂料层具有的k值范围为0.05-1.0和/或第二抗反射涂料层具有的k值范围为0.05-0.5。
13.如权利要求11所述的方法,其中所述第二抗反射涂料层包含硅。
14.如权利要求11所述的方法,其中所述光刻胶是用240nm-12nm的辐射可成像的。
15.如权利要求11-14中任一项所述的方法,其中所述显影水溶液是含氢氧化物碱的水溶液。
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