TWI712583B - 化合物及有機膜形成用組成物 - Google Patents
化合物及有機膜形成用組成物 Download PDFInfo
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- TWI712583B TWI712583B TW108121174A TW108121174A TWI712583B TW I712583 B TWI712583 B TW I712583B TW 108121174 A TW108121174 A TW 108121174A TW 108121174 A TW108121174 A TW 108121174A TW I712583 B TWI712583 B TW I712583B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 146
- 239000000203 mixture Substances 0.000 title claims description 117
- 125000000962 organic group Chemical group 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000004429 atom Chemical group 0.000 claims abstract description 26
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
- -1 sulfoxy Chemical group 0.000 claims description 58
- 230000015572 biosynthetic process Effects 0.000 claims description 52
- 239000003431 cross linking reagent Substances 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 239000000758 substrate Substances 0.000 abstract description 100
- 238000001312 dry etching Methods 0.000 abstract description 24
- 238000011049 filling Methods 0.000 abstract description 17
- 238000012545 processing Methods 0.000 abstract description 15
- 239000006227 byproduct Substances 0.000 abstract description 9
- 125000000129 anionic group Chemical group 0.000 abstract description 5
- 239000012298 atmosphere Substances 0.000 abstract description 4
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- 239000011261 inert gas Substances 0.000 abstract 1
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- 229910052710 silicon Inorganic materials 0.000 description 68
- 239000010410 layer Substances 0.000 description 65
- 239000010703 silicon Substances 0.000 description 65
- 239000000543 intermediate Substances 0.000 description 62
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- 230000000052 comparative effect Effects 0.000 description 36
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- 230000002829 reductive effect Effects 0.000 description 28
- 238000009835 boiling Methods 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000003153 chemical reaction reagent Substances 0.000 description 23
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 229910052814 silicon oxide Inorganic materials 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- 238000001816 cooling Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 239000011229 interlayer Substances 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 229910004298 SiO 2 Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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- 230000003667 anti-reflective effect Effects 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 125000002524 organometallic group Chemical group 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
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- 239000006185 dispersion Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000004795 grignard reagents Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 125000001979 organolithium group Chemical group 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
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- 230000007261 regionalization Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000005979 thermal decomposition reaction Methods 0.000 description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910052581 Si3N4 Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
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- 150000001768 cations Chemical class 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
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- 239000002356 single layer Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- XXFUZSHTIOFGNV-UHFFFAOYSA-N 1-bromoprop-1-yne Chemical compound CC#CBr XXFUZSHTIOFGNV-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
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- 230000008859 change Effects 0.000 description 3
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- 239000010949 copper Substances 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
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- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 3
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- 238000000206 photolithography Methods 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 2
- LNNXOEHOXSYWLD-UHFFFAOYSA-N 1-bromobut-2-yne Chemical compound CC#CCBr LNNXOEHOXSYWLD-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
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- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
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- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000005591 trimellitate group Chemical group 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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Abstract
Description
本發明關於例如使用在半導體裝置製造步驟等的化合物、含有該化合物之有機膜形成用組成物。
以往,半導體裝置之高整合化與高速化,係利用作為泛用技術之使用了光曝光之微影技術(光微影)中之光源的短波長化所獲致之圖案尺寸之微細化而達成。為了在半導體裝置基板(被加工基板)上形成如此之微細的電路圖案,通常使用以形成有圖案之光阻膜作為蝕刻遮罩,並利用乾蝕刻對被加工基板進行加工的方法。但是現實上,並不存在可在光阻膜與被加工基板之間取得完全的蝕刻選擇性的乾蝕刻方法,故近年一般係利用多層光阻法來進行基板加工。該方法係如下之方法:使蝕刻選擇性與光阻膜(以下稱為光阻上層膜)不同的中間膜介在於光阻上層膜與被加工基板之間,在光阻上層膜獲得圖案後,以光阻上層膜圖案作為乾蝕刻遮罩,利用乾蝕刻將圖案轉印至中間膜,再以中間膜作為乾蝕刻遮罩,並利用乾蝕刻將圖案轉印至被加工基板。
作為多層光阻法之一,有可使用單層光阻法中所使用之一般的光阻組成物來實施的3層光阻法。該方法係藉由於被加工基板上使用由含有有機樹脂之組成物構成的有機下層膜材料進行塗布、煅燒而將有機下層膜(以下稱為有機膜)予以成膜,並藉由在其上使用由含有含矽樹脂之組成物構成的光阻中間膜材料進行塗布、煅燒而成膜為含矽膜(以下稱為矽中間膜),並於其上形成一般的光阻上層膜。將該光阻上層膜圖案化後,實施利用氟系氣體電漿所為之乾蝕刻的話,有機系光阻上層膜相對於矽中間膜可獲得良好的蝕刻選擇比,故可將光阻上層膜圖案轉印至矽中間膜。根據該方法,即使使用不具有直接加工被加工基板所需之充分膜厚的光阻上層膜、不具有被加工基板之加工所需之充分乾蝕刻耐性的光阻上層膜,由於相較於光阻上層膜,矽中間膜通常為同等以下之膜厚,故仍可輕易地將圖案轉印至矽中間膜。然後,藉由以轉印有圖案之矽中間膜作為乾蝕刻遮罩,並利用氧系或氫系氣體電漿所為之乾蝕刻將圖案轉印至有機下層膜的話,即可對具有基板之加工所需之充分乾蝕刻耐性的有機下層膜進行圖案轉印。將該轉印有圖案之有機下層膜圖案使用氟系氣體、氯系氣體等進行乾蝕刻,可將圖案轉印至基板。
另一方面,半導體裝置之製造步驟中的微細化,已逐漸趨近來自光微影用光源之波長的固有極限。因此,近年來已有人研究不依賴於微細化的半導體裝置之高整合化,就其方法之一而言,有人研究具有多閘極結構、環繞式閘極(Gate-all-around)等複雜結構的半導體裝置,一部分已經實用化。利用多層光阻法形成如此之結構時,可使用能以有機膜材料無空隙地填埋被加工基板上已形成之孔、溝渠、鰭等微小圖案,或以有機膜材料填埋高低差、圖案密集部分及無圖案之區域並且平坦化(planarization)的有機膜材料。藉由使用如此之有機膜材料在高低差基板上形成平坦的有機下層膜表面,可抑制在其上成膜之矽中間膜、光阻上層膜的膜厚變動,並可抑制光微影之焦點裕度、之後的被加工基板之加工步驟中之寬容度下降。藉此,能以良好的良率製造半導體裝置。另一方面,單層光阻法中,為了填埋存有高低差、圖案之被加工基板,上層光阻膜之膜厚會加厚,因而導致曝光顯影後之圖案崩塌、由於曝光時來自基板之反射導致圖案形狀劣化等,曝光時之圖案形成裕度變窄,不易以良好的良率製造半導體裝置。
另外,作為次世代之半導體裝置之高速化的方法,例如,已有人開始研究使用了應變矽晶(strained silicon)、鎵砷等之電子移動度高的新穎材料、控制在埃單位之超薄膜多晶矽等精密材料的採用。但是,採用了如此之新穎的精密材料的被加工基板,於以如上述之有機下層膜材料進行平坦化膜形成時之條件,例如以空氣中、300℃以上之成膜條件,會因空氣中的氧而導致該材料腐蝕,半導體裝置之高速化無法發揮原本材料設計的性能,可能會無法達到工業化生產需要的良率。因此,為了避免因為如此之高溫條件下之空氣導致基板腐蝕所造成的良率降低,期待有可於鈍性氣體中成膜的有機下層膜材料。
以往,就多層光阻法用之有機膜形成用材料而言,已知有對於苯酚系、萘酚系化合物使用作為縮合劑之酮類、醛類等羰基化合物、芳香族醇類而得的縮合樹脂類。例如可例示:專利文獻1記載之茀雙酚酚醛清漆樹脂、專利文獻2記載之雙酚化合物及其酚醛清漆樹脂、專利文獻3記載之金剛烷苯酚化合物之酚醛清漆樹脂、專利文獻4記載之雙萘酚化合物及其酚醛清漆樹脂等。如此之材料,係利用使用羥甲基化合物作為交聯劑所為之交聯、利用空氣中之氧之作用使芳香環之α位氧化與之後之縮合所為之交聯反應引起的硬化作用,而成膜為對於之後步驟使用之塗布膜材料具有溶劑耐性的膜。
進一步,就使用參鍵作為硬化性樹脂之分子間交聯基的材料之示例而言,已知有專利文獻5~10等。但是,該等材料就硬化條件而言實際上並無於鈍性氣體中之例示,該等材料於鈍性氣體中之硬化膜的形成、因高溫條件下之熱分解所致之膜厚變動等則不得而知。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2005-128509號公報
[專利文獻2]日本特開2006-293298號公報
[專利文獻3]日本特開2006-285095號公報
[專利文獻4]日本特開2010-122656號公報
[專利文獻5]日本特開2010-181605號公報
[專利文獻6]WO2014-208324號
[專利文獻7]日本特開2012-215842號公報
[專利文獻8]日本特開2016-044272號公報
[專利文獻9]日本特開2016-060886號公報
[專利文獻10]日本特開2017-119671公報
[發明所欲解決之課題]
本發明係鑒於上述情事而成,旨在提供一種化合物,不僅在空氣中會硬化,在鈍性氣體中之成膜條件下亦會硬化,且不會產生揮發性的副產物,可形成耐熱性、已形成在基板之圖案的填埋、平坦化特性優異,而且基板加工時之乾蝕刻耐性亦良好的有機下層膜;並旨在提供使用了該化合物之有機膜形成用組成物、及就用以獲得該化合物之中間體而言理想的化合物。
[解決課題之手段]
為了解決上述課題,本發明提供一種化合物,係以下列通式(1-1)表示。
[化1]
式中,AR1、AR2各自獨立地表示也可具有取代基之芳香環、或也可具有取代基之含有氮原子、硫原子中之至少1個的芳香環,2個AR1彼此、AR1與AR2、或2個AR2彼此也可連接並形成環結構。AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環。A為碳數1~30之有機基,B為可藉由熱、酸中之任一者或兩者的作用而生成反應性陽離子的陰離子性脫離基,Y為亦可含有1個以上之氧的碳數為1~10之2價有機基,p為1或2,q為1或2,r為0或1,s為2~4。s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
本發明之化合物係如下之化合物:不僅在空氣中可交聯,在鈍性氣體中亦可交聯並形成有機膜,且不會產生副產物,可形成耐熱性、已形成在基板之圖案的填埋、平坦化特性優異,而且基板加工時之乾蝕刻耐性亦良好的有機下層膜。又,藉由該化合物之交聯獲得的有機膜,係形成CVD-硬遮罩時不會發生因熱分解所致之膜厚變動的有機膜。
又,此時,前述化合物宜為下列通式(1-2)表示者。
[化2]
式中,AR3如前述,AR4、AR5為也可具有取代基之苯環、萘環、噻吩環或吡啶環,m為0或1,m=0時,AR4、AR5不形成橋聯結構,m=1時,AR4、AR5介隔著X並形成橋聯結構,X為單鍵或下式(1-2-1)中之任一者,s、Z如前述。
[化3]
如此,本發明之上述化合物宜為上述通式(1-2)表示之化合物、上述通式(1-3)表示之化合物。
又,本發明提供一種有機膜形成用組成物,其特徵為含有(A)下列通式(1-1)表示之化合物、及(B)有機溶劑。
[化5]
式中,AR1、AR2各自獨立地表示也可具有取代基之芳香環、或也可具有取代基之含有氮原子、硫原子中之至少1個的芳香環,2個AR1彼此、AR1與AR2、或2個AR2彼此也可連接並形成環結構。AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環,A為碳數1~30之有機基,B為可藉由熱、酸中之任一者或兩者的作用而生成反應性陽離子的陰離子性脫離基,Y為亦可含有1個以上之氧的碳數為1~10之2價有機基,p為1或2,q為1或2,r為0或1,s為2~4。s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
本發明之有機膜形成用組成物,係可於鈍性氣體中形成兼具高耐熱性、高乾蝕刻耐性、高程度填埋/平坦化特性之有機膜的有機膜形成用組成物。
此時,前述(A)之化合物宜為下列通式(1-2)表示之化合物。
[化6]
式中,AR3如前述。AR4、AR5為也可具有取代基之苯環、萘環、噻吩環或吡啶環,m為0或1,m=0時,AR4、AR5不形成橋聯結構,m=1時,AR4、AR5介隔著X並形成橋聯結構,X為單鍵或下式(1-2-1)中之任一者。s、Z如前述。
[化7]
如此,上述(A)之化合物宜為上述通式(1-2)表示之化合物、上述通式(1-3)表示之化合物。
本發明之有機膜形成用組成物可更含有(C)酸產生劑、(D)界面活性劑、(E)交聯劑、及(F)塑化劑中之1種以上。
本發明之有機膜形成用組成物,亦可因應目的含有上述(C)~(F)成分中之1種以上。
又,本發明提供一種化合物,係以下列通式(1-4)表示。
[化9]
式中,AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環。AR6、AR7為也可具有取代基之苯環、萘環、噻吩環、或吡啶環。m為0或1,m=0時,AR6、AR7不形成橋聯結構,m=1時,AR6、AR7介隔著X並形成橋聯結構。X為單鍵或下式(1-2-1)中之任一者,AR6與AR7藉由單鍵連接時,AR6與AR7中之至少一者不為苯環。s為2~4,s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
[化10]
又,本發明提供一種化合物,係以下列通式(1-5)表示。
[化11]
式中,AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環。AR6、AR7為也可具有取代基之苯環、萘環、噻吩環、或吡啶環。m為0或1,m=0時,AR6、AR7不形成橋聯結構,m=1時,AR6、AR7介隔著X並形成橋聯結構。X為單鍵或下式(1-2-1)中之任一者,AR6與AR7藉由單鍵連接時,AR6與AR7中之至少一者不為苯環。s為2~4,s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
[化12]
本發明之上述通式(1-4)表示之化合物及通式(1-5)表示之化合物,適合作為製造通式(1-1)表示之化合物時的中間體,該通式(1-1)表示之化合物係可於鈍性氣體中形成兼具高耐熱性、高乾蝕刻耐性、高程度填埋/平坦化特性之有機膜的有機膜形成用材料。
[發明之效果]
如以上說明般,本發明之上述(1-1)表示之化合物,係於防止基板腐蝕之鈍性氣體中成膜時,可在不產生揮發性副產物的情況下硬化,且對於形成兼具高程度填埋及平坦化特性之有機下層膜係有用的化合物。又,含有該化合物之有機膜形成用組成物,係會形成具有優異填埋/平坦化特性,而且兼具耐熱性、蝕刻耐性等各種特性之有機膜的材料。因此,例如作為諸如2層光阻法、使用了矽中間膜之3層光阻法、使用了矽中間膜及有機抗反射膜之4層光阻法的多層光阻法中之有機膜材料、或作為半導體裝置製造用平坦化材料係極為有用。又,由本發明之有機膜形成用組成物形成的有機膜的耐熱性優異,故即使在該有機下層膜上形成CVD硬遮罩時,亦不會因熱分解而發生膜厚變動,適合用於圖案形成。
如上述,需要如下之有機下層膜:即使於為了防止基板腐蝕之鈍性氣體中之成膜條件,例如300℃以上亦不會產生揮發性的副產物,又,已形成在基板上之圖案的填埋、平坦化特性優異,基板加工時之乾蝕刻耐性亦良好。進一步,需要即使在該有機下層膜上形成CVD硬遮罩時,亦不會因分解而發生膜厚變動的有機膜,希望開發出實現該等特性的有機膜形成用化合物。
通常形成有機下層膜時,係將有機膜形成用化合物以有機溶劑溶解,製成組成物,並將其塗布在形成有半導體裝置之結構、配線等的基板上,進行煅燒而形成有機下層膜。組成物剛塗布時會形成沿著基板上之高低差結構之形狀的塗布膜,但將該塗布膜進行煅燒的話,在直到硬化為止的期間,有機溶劑大部分會蒸發,而藉由殘留在基板上之有機膜形成用化合物形成有機膜。本案發明人等想到此時殘留在基板上之有機膜形成用化合物若具有充分的熱流動性的話,則可藉由熱流動使剛塗布時之高低差形狀平坦化,而形成平坦的膜。
本案發明人等進一步研究發現:為了提供具有高耐熱性,且於為了防止基板腐蝕而不含氧之鈍性氣體中會硬化的材料,就達成如此之硬化反應的結構而言,具有以通式(1-1)表示之1個以上之參鍵作為取代基並作為分子間交聯基的化合物,藉由含有有效配置之參鍵的取代基,於空氣中及鈍性氣體中之成膜條件下具有熱硬化性,即使在鈍性氣體中亦展現出與習知下層膜材料同等的硬化性能,且硬化反應時不會產生副產物,又,藉由有效配置之芳香環,具有高耐熱性。又,由於熱流動性良好,故可提供具有高程度填埋/平坦化特性,且具有良好乾蝕刻耐性,並兼具即使形成CVD硬遮罩時亦不會因熱分解而發生塗布膜厚變動之耐熱性的有機膜形成用組成物,而完成了本發明。
以下,針對本發明進行詳細地說明,但本發明並不限定於該等。
<化合物(1)>
亦即,本發明係下列通式(1-1)表示之化合物(以下,稱為化合物(1))。
[化13]
式中,AR1、AR2各自獨立地表示也可具有取代基之芳香環、或也可具有取代基之含有氮原子、硫原子中之至少1個的芳香環,2個AR1彼此、AR1與AR2、或2個AR2彼此也可連接並形成環結構。AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環。A為碳數1~30之有機基,B為可藉由熱、酸中之任一者或兩者的作用而生成反應性陽離子的陰離子性脫離基,Y為亦可含有1個以上之氧的碳數為1~10之2價有機基,p為1或2,q為1或2,r為0或1,s為2~4。s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
AR1、AR2各自獨立地表示也可具有取代基之芳香環、或也可具有取代基之含有氮原子、硫原子中之至少1個的芳香環,2個AR1彼此、AR1與AR2、或2個AR2彼此也可連接並形成環結構。如此之AR1、AR2,例如可列舉也可具有取代基之苯環、萘環、噻吩環、吡啶環等。就取代基而言,例如可列舉烷基、烷氧基等。
A表示碳數1~30之有機基,例如為烷基,尤其宜為甲基。B為可藉由熱、酸中之任一者或兩者的作用而生成反應性陽離子的陰離子性脫離基,例如可列舉羥基、烷氧基、醯氧基、磺醯氧基等。Y為亦可含有1個以上之氧的碳數為1~10之2價有機基,尤其宜為含有1個氧的碳數1~5之有機基。
p為1或2,q為1或2,r為0或1,s為2~4。s=2時,Z為單鍵、2價原子(例如,氧原子、硫原子等)、或2價有機基。又,s=3或4時,Z為3價或4價的原子(例如,氮原子、碳原子等)或有機基。
更具體而言,化合物(1)為下列通式(1-2)表示之化合物(2)、或下列通式(1-3)表示之化合物(3)。
[化14]
式中,AR3如前述,AR4、AR5為也可具有取代基之苯環、萘環、噻吩環或吡啶環,m為0或1,m=0時,AR4、AR5不形成橋聯結構,m=1時,AR4、AR5介隔著X並形成橋聯結構,X為單鍵或下式(1-2-1)中之任一者,s、Z如前述。
[化15]
上述化合物(1)之中,宜為上述通式(1-2)表示之化合物。化合物(2)可例示如下,但並不限定於該等。
又,本發明提供下列通式(1-4)表示之化合物(4)、及下列通式(1-5)表示之化合物(5)作為上述化合物(2)之有用的合成中間體。
[化28]
式中,AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環。AR6、AR7為也可具有取代基之苯環、萘環、噻吩環、或吡啶環。m為0或1,m=0時,AR6、AR7不形成橋聯結構,m=1時,AR6、AR7介隔著X並形成橋聯結構。X為單鍵或下式(1-2-1)中之任一者,AR6與AR7藉由單鍵連接時,AR6與AR7中之至少一者不為苯環。s為2~4,s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
[化29]
[化30]
式中,AR3為也可具有取代基之苯環、萘環、噻吩環、吡啶環、或二環。AR6、AR7為也可具有取代基之苯環、萘環、噻吩環、或吡啶環。m為0或1,m=0時,AR6、AR7不形成橋聯結構,m=1時,AR6、AR7介隔著X並形成橋聯結構。X為單鍵或下式(1-2-1)中之任一者,AR6與AR7藉由單鍵連接時,AR6與AR7中之至少一者不為苯環。s為2~4,s=2時,Z為單鍵、2價原子、或2價有機基,s=3或4時,Z為3價或4價的原子或有機基。
化合物(4)之具體例可例示化合物(2)之甲基炔丙氧基變為羥基的結構(惟,通式(1-2)中之AR4、AR5藉由單鍵連接時,AR4與AR5中之至少一者不為苯環的結構),但並不限定於該等。該等化合物如後述般係用以合成化合物(2)之有用的中間體。又,該等化合物本身亦可使用於有機膜形成用組成物。
化合物(5)之具體例可例示化合物(2)之甲基炔丙氧基變為炔丙氧基的結構(惟,通式(1-2)中之AR4、AR5藉由單鍵連接時,AR4與AR5中之至少一者不為苯環的結構),但並不限定於該等。該等化合物如後述般係用以合成化合物(2)之有用的中間體。又,該等化合物本身亦可使用於有機膜形成用組成物。
[化合物之製造方法]
本發明之化合物(2),亦即上述通式(1-2)表示之化合物的製造方法之一例如下所示。惟,化合物(2)之製造方法並不限定於此。
可經由如下途徑:首先,藉由下列有機金屬試劑(ii)對於酮化合物(i)之加成反應獲得(iii),使(iii)與萘酚反應而得到化合物(iv),特別是得到上述通式(1-4)表示之化合物(4)作為中間體。進一步,使該中間體(iv)與3-鹵化丙炔(炔丙基鹵化物)反應而得到化合物(v),特別是得到上述通式(1-5)表示之化合物作為後續的中間體,將其甲基化,可獲得下列通式(1-2)。或使係中間體之化合物(iv),特別是使上述通式(1-4)與1-鹵化-2-丁炔(甲基炔丙基鹵化物)反應,亦可獲得下列通式(1-2)。
此時,相對於式(i)之酮化合物1莫耳,宜使用0.2/s~40/s莫耳之有機金屬試劑(ii),尤其宜使用0.5/s~2/s莫耳。
有機金屬試劑(ii)可例示Grignard試劑、有機鋰試劑、有機鋅試劑、有機鈦試劑等,為Grignard試劑、有機鋰試劑特佳。Grignard試劑與有機鋰試劑可利用對應的鹵化物與金屬鎂或金屬鋰之直接金屬化來製備,亦可利用與異丙基鹵化鎂、或甲基鋰、丁基鋰等脂肪族有機金屬化合物之金屬-鹵素交換反應來製備。又,有機鋅試劑、有機鈦試劑可由對應的Grignard試劑或有機鋰試劑利用與鹵化鋅、或鹵化鈦(IV)、烷氧基鈦(IV)等之反應來製備。
該等有機金屬試劑(ii)之製備時、及/或該等有機金屬試劑與酮化合物(i)之反應時亦可使金屬鹽化合物共存。就金屬鹽化合物而言,可列舉氰化物、鹵化物、過鹵酸鹽,尤其可理想地例示氯化鋰、溴化鋰、碘化鋰、過氯酸鋰等鋰鹽類、氰化銅(I)、氰化銅(II)、氯化銅(I)、氯化銅(II)、四氯合銅二鋰(dilithium tetrachlorocuprate)等銅鹽類。該等金屬鹽化合物,藉由相對於有機金屬試劑添加0.01~5.0當量,較佳為添加0.2~2.0當量,可增加有機金屬試劑之溶解性而使其製備變得容易,或可調節試劑的親核性、Lewis酸性。
有機金屬試劑(ii)之製備及與酮化合物(i)之反應中使用的溶劑,可單獨或混合使用:二乙醚、二丁醚、四氫呋喃、1,4-二㗁烷、環戊基甲醚、第三丁基甲醚等醚類;苯、甲苯、二甲苯、均三甲苯、己烷、庚烷、辛烷、異辛烷等烴類;N,N,N’,N’-四甲基乙二胺、六甲基磷醯三胺、N,N-二甲基甲醯胺等非質子性極性溶劑類。反應溫度取決於酮化合物(i)、有機金屬試劑(ii)的種類、反應條件,但宜為-70~150℃,例如(ii)為有機鋰試劑時可選擇-70~10℃,為Grignard試劑時可選擇室溫~溶劑之沸點之回流下等。就反應時間而言,利用層析法等追蹤反應以完成反應較理想,通常實施30分鐘至48小時即可。
(iii)與萘酚之脫水縮合反應,通常於無溶劑或溶劑中使用酸或鹼作為觸媒,在室溫或視需要在冷卻或加熱下實施。就所使用之溶劑而言,可例示:甲醇、乙醇、異丙醇、丁醇、乙二醇、丙二醇、二乙二醇、甘油等醇類;乙二醇單甲醚、丙二醇單甲醚、二乙醚、二丁醚、二乙二醇二乙醚、二乙二醇二甲醚、四氫呋喃、1,4-二㗁烷等醚類;二氯甲烷、氯仿、二氯乙烷、三氯乙烯等氯系溶劑類;己烷、庚烷、苯、甲苯、二甲苯、異丙苯等烴類;乙腈等腈類;丙酮、甲乙酮、異丁基甲基酮等酮類;乙酸乙酯、乙酸正丁酯、丙二醇甲醚乙酸酯等酯類;二甲基亞碸、N,N-二甲基甲醯胺、六甲基磷醯三胺等非質子性極性溶劑類,該等可單獨使用或混合使用2種以上。就所使用之酸觸媒而言,可使用:鹽酸、氫溴酸、硫酸、硝酸、磷酸、雜多酸等無機酸類;草酸、三氟乙酸、甲磺酸、苯磺酸、對甲苯磺酸、三氟甲磺酸等有機酸類;三氯化鋁、乙氧基鋁、異丙氧基鋁、三氟化硼、三氯化硼、三溴化硼、四氯化錫、四溴化錫、二氯化二丁基錫、二甲氧基二丁基錫、二丁基氧化錫、四氯化鈦、四溴化鈦、甲氧基鈦(IV)、乙氧基鈦(IV)、異丙氧基鈦(IV)、氧化鈦(IV)等路易士酸類。就所使用之鹼觸媒而言,可使用:氫氧化鈉、氫氧化鉀、氫氧化鋇、碳酸鈉、碳酸氫鈉、碳酸鉀、氫化鋰、氫化鈉、氫化鉀、氫化鈣等無機鹼類;甲基鋰、正丁基鋰、甲基氯化鎂、乙基溴化鎂等烷基金屬類;甲氧基鈉、乙氧基鈉、第三丁氧基鉀等醇鹽類;三乙胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、4-二甲基胺基吡啶等有機鹼類。反應溫度宜為-50℃~約溶劑之沸點,為室溫~100℃更佳。
化合物(iv)(特別是上述通式(1-4)表示之化合物)與3-鹵化丙炔(炔丙基鹵化物)或1-鹵化-2-丁炔(甲基炔丙基鹵化物)之反應,可例示使用了鹼的取代反應、使用了過渡金屬觸媒的偶聯反應等。取代反應所使用之鹼可列舉:碳酸氫鈉、碳酸鈉、碳酸鉀、碳酸鈣、碳酸銫、氫氧化鈉、氫氧化鉀、氫化鈉、磷酸鉀等無機鹼化合物;甲氧基鈉、乙氧基鈉、第三丁氧基鉀等醇鹽;三乙胺、吡啶、N-甲基啉等有機胺化合物;Grignard試劑、有機鋰試劑、Li、Na等金屬,該等可單獨使用或將2種以上組合使用。又,使用過渡金屬觸媒時,可使用銅粉末、氯化銅、溴化銅、碘化銅、乙酸銅、氫氧化銅、硝酸銅等銅觸媒、參(二亞苄基丙酮)二鈀、肆(三苯基膦)鈀等,亦可將該等與前述鹼組合。
就反應方法而言,可列舉:一次性加入化合物(iv)(特別是上述通式(1-4)表示之化合物)、鹵化物、及鹼的方法;將上述化合物(iv)與鹵化物予以分散或溶解後,一次性添加或以溶劑稀釋後滴加鹼的方法;或將鹼予以分散或溶解後,一次性添加或以溶劑稀釋後滴加化合物(iv)與鹵化物的方法,宜為使化合物(iv)與鹼反應而產生陰離子,然後加入鹵化物的方法。
作為此時所使用之溶劑,只要是對於上述反應係鈍性的溶劑,則並無特別限制,例如可單獨或混合使用:二乙醚、四氫呋喃、二㗁烷等醚系溶劑;苯、甲苯、二甲苯等芳香族系溶劑;乙腈、二甲基亞碸、N,N-二甲基甲醯胺、N-甲基吡咯烷酮等非質子性極性溶劑;水。反應溫度宜為-50℃~約溶劑之沸點,為室溫~100℃更佳。就反應時間而言,利用層析法等追蹤反應以完成反應較理想,通常實施30分鐘至48小時即可。
反應結束後,為了將系內存在的未反應原料、酸觸媒等除去,亦可利用有機溶劑稀釋後進行以分液所為之水洗處理,並予以回收。
分液洗淨時使用之有機溶劑,只要是可溶解化合物且與水混合則分為2層者,則並無特別限制,可列舉:己烷、庚烷、苯、甲苯、二甲苯等烴類;乙酸乙酯、乙酸正丁酯、丙二醇甲醚乙酸酯等酯類;甲乙酮、甲基戊基酮、環己酮、甲基異丁基酮等酮類;二乙醚、二異丙醚、甲基-第三丁醚、環戊基甲醚等醚類;二氯甲烷、氯仿、二氯乙烷、三氯乙烯等氯系溶劑類;及它們的混合物等。
分液洗淨時為了除去系內之未反應原料或酸性成分,亦可利用鹼性水溶液進行洗淨。鹼性水溶液中含有的鹼,具體而言,可列舉鹼金屬之氫氧化物、鹼金屬之碳酸鹽、鹼土金屬之氫氧化物、鹼土金屬之碳酸鹽、氨、及有機銨等。
另外,分液洗淨時為了除去系內之未反應原料、金屬雜質或鹼成分,也可利用酸性水溶液進行洗淨。酸性水溶液中含有的酸,具體而言,可列舉:鹽酸、氫溴酸、硫酸、硝酸、磷酸、雜多酸等無機酸類;草酸、三氟乙酸、甲磺酸、苯磺酸、對甲苯磺酸、三氟甲磺酸等有機酸類等。
上述以鹼性水溶液、酸性水溶液所為之分液洗淨可僅進行其中任一者,亦可組合進行。考量除去金屬雜質的觀點,分液洗淨宜按照鹼性水溶液、酸性水溶液的順序進行。
上述以鹼性水溶液、酸性水溶液所為之分液洗淨後,亦可利用中性水進行洗淨。洗淨次數只要進行1次以上即可,宜為約1~5次。中性水可使用去離子水、超純水等。洗淨次數若為1次以上,則可充分除去鹼成分、酸性成分,故較佳。為了獲得洗淨效果,10次即足夠,宜為約1~5次。
另外,分液洗淨後之反應產物也可於減壓或常壓下將溶劑進行濃縮乾固或晶析操作而以粉體的形式回收,但為了改善製備有機膜形成用組成物時之操作性,也可預先使其成為適度濃度之溶液狀態。此時的濃度宜為0.1~50質量%,更佳為0.5~30重量%。若為如此之濃度,黏度不易變高,因此可防止損及操作性,又,溶劑的量不會變得過大,有經濟性。
就此時的溶劑而言,只要是可溶解聚合物者,則並無特別限制,舉具體例的話,可列舉:環己酮、甲基-2-戊基酮等酮類;3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇等醇類;丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚等醚類;丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、乳酸乙酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯等酯類,該等可單獨使用或將2種以上混合使用。
由化合物(v)(特別是上述通式(1-5)表示之化合物)獲得上述通式(1-2)的反應,可列舉使用鹼之與甲基碘或硫酸二甲酯之取代反應。取代反應中使用的鹼可列舉:碳酸氫鈉、碳酸鈉、碳酸鉀、碳酸鈣、碳酸銫、氫氧化鈉、氫氧化鉀、氫化鈉、磷酸鉀等無機鹼化合物;甲氧基鈉、乙氧基鈉、第三丁氧基鉀等醇鹽;三乙胺、吡啶、N-甲基啉等有機胺化合物;Grignard試劑、有機鋰試劑、Li、Na等金屬,該等可單獨使用或將2種以上組合使用。作為此時所使用的溶劑,可單獨或混合使用:二乙醚、二丁醚、四氫呋喃、1,4-二㗁烷、環戊基甲醚、第三丁基甲醚等醚類;苯、甲苯、二甲苯、均三甲苯、己烷、庚烷、辛烷、異辛烷等烴類;N,N,N’,N’-四甲基乙二胺、六甲基磷醯三胺、N,N-二甲基甲醯胺等非質子性極性溶劑類。反應溫度取決於上述通式(1-5)表示之化合物、鹼的種類、反應條件,但宜為-70~150℃,例如鹼為有機鋰試劑時可選擇-70~10℃,為Grignard試劑時可選擇室溫~溶劑之沸點之回流下等。
針對本發明之通式(1-2)表示之化合物的設計思想進行敘述。
本發明之通式(1-2)表示之化合物由於具有參鍵結構,即使於無氧條件下亦會熱硬化,且藉由有效地配置多個芳香環,而實現更高的耐熱性。故,係適合於要求在鈍性氣體中硬化成膜,且此時不會產生副產物之微影用有機下層膜的化合物。另外,相較於同樣具有參鍵之炔丙基時,具有甲基炔丙基之本發明之化合物的材料熱流動性得到改善,又,熱硬化開始的溫度高,故加熱成膜時化合物的熱流動更容易發生。該特性有助於改善在基板上形成之圖案的填埋特性、平坦化特性。
如上,本發明之化合物即使於鈍性氣體中亦可硬化,並提供兼具400℃以上之耐熱性及高程度填埋/平坦化特性的有機膜形成用組成物。
此外,本發明中,平坦化特性係指使基板之表面平坦化的性能。若為含有本發明之通式(1-1)表示之化合物的組成物,例如如圖1所示般,藉由於基板1上塗布有機膜形成用組成物3’,並進行加熱以形成有機膜3,可將基板1之100nm之高低差減小至30nm以下。此外,圖1所示之高低差形狀,係展示於半導體裝置製造用基板之高低差形狀的代表例,可藉由含有本發明之通式(1-1)表示之化合物之組成物而平坦化的基板之高低差形狀當然不限定於此。
<有機膜形成用組成物>
又,本發明提供一種有機膜形成用組成物,含有(A)上述通式(1-1)表示之本發明之化合物及(B)有機溶劑。此外,本發明之有機膜形成用組成物中,上述本發明之通式(1-1)表示之化合物可單獨使用1種或將2種以上組合使用。
本發明之有機膜形成用組成物中可使用之(B)有機溶劑,只要會使前述基礎聚合物、酸產生劑、交聯劑、其他添加劑等溶解,則並無特別限制。具體而言,可使用日本特開2007-199653號公報中之段落(0091)~(0092)記載之溶劑等沸點未達180℃的溶劑。其中,可理想地使用丙二醇單甲醚乙酸酯、丙二醇單甲醚、2-庚酮、環戊酮、環己酮及該等中之2種以上之混合物。
若為如此之組成物,可利用旋轉塗布進行塗布,又,由於含有如上述之本發明之化合物(A),會成為具有良好乾蝕刻耐性,且兼具400℃以上之耐熱性及高程度填埋/平坦化特性的有機膜形成用組成物。
進一步,本發明之有機膜形成用組成物中,亦可於上述沸點未達180℃之溶劑中添加沸點為180℃以上之高沸點溶劑(可混合使用沸點未達180℃之溶劑與沸點為180℃以上之溶劑)作為有機溶劑。高沸點有機溶劑只要可溶解有機膜形成用化合物即可,不特別限於烴類、醇類、酮類、酯類、醚類、氯系溶劑等,具體例可例示:1-辛醇、2-乙基己醇、1-壬醇、1-癸醇、1-十一醇、乙二醇、1,2-丙二醇、1,3-丁二醇、2,4-戊烷二醇、2-甲基-2,4-戊烷二醇、2,5-己烷二醇、2,4-庚烷二醇、2-乙基-1,3-己烷二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、甘油、乙酸正壬酯、乙二醇單己醚、乙二醇單-2-乙基己醚、乙二醇單苯醚、乙二醇單苄醚、二乙二醇單乙醚、二乙二醇單異丙醚、二乙二醇單-正丁醚、二乙二醇單異丁醚、二乙二醇單己醚、二乙二醇單苯醚、二乙二醇單苄醚、二乙二醇二乙醚、二乙二醇二丁醚、二乙二醇丁基甲醚、三乙二醇二甲醚、三乙二醇單甲醚、三乙二醇-正丁醚、三乙二醇丁基甲醚、三乙二醇二乙酸酯、四乙二醇二甲醚、二丙二醇單甲醚、二丙二醇單-正丙醚、二丙二醇單-正丁醚、三丙二醇二甲醚、三丙二醇單甲醚、三丙二醇單-正丙醚、三丙二醇單-正丁醚、乙二醇單乙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、三乙酸甘油酯、丙二醇二乙酸酯、二丙二醇單甲醚乙酸酯、二丙二醇甲基-正丙醚、二丙二醇甲醚乙酸酯、1,4-丁烷二醇二乙酸酯、1,3-丁二醇二乙酸酯、1,6-己烷二醇二乙酸酯、三乙二醇二乙酸酯、γ-丁內酯、丙二酸二己酯、琥珀酸二乙酯、琥珀酸二丙酯、琥珀酸二丁酯、琥珀酸二己酯、己二酸二甲酯、己二酸二乙酯、己二酸二丁酯等,該等可單獨使用或混合使用。
上述高沸點溶劑的沸點,配合將有機膜形成用組成物進行熱處理之溫度適當選擇即可,所添加之高沸點溶劑的沸點宜為180℃~300℃,為200℃~300℃更佳。若為如此之沸點,則不會有因沸點過低導致烘烤(熱處理)時溶劑瞬間揮發之虞,而可獲得充分的熱流動性。又,若為如此之沸點,則不會有於烘烤後仍不揮發而殘留在膜中的情形,而不會有對蝕刻耐性等膜物性造成不良影響之虞。
又,使用上述高沸點溶劑時,高沸點溶劑的摻合量相對於沸點未達180℃之溶劑100質量份,宜為1~30質量份。若為如此之摻合量,則不會有因摻合量過少導致烘烤時無法獲得充分的熱流動性,或因摻合量過多而殘留在膜中導致蝕刻耐性等膜物性劣化之虞。
若為如此之有機膜形成用組成物,則藉由於上述本發明之化合物(A)添加高沸點溶劑而賦予熱流動性,會成為兼具更高程度的填埋/平坦化特性之有機膜形成用組成物。
本發明之有機膜形成用組成物中,為了進一步促進硬化反應,可添加(C)酸產生劑。酸產生劑有因熱分解而產生酸者、因光照射而產生酸者,皆可添加。具體而言,可添加日本特開2007-199653號公報中之段落(0061)~(0085)記載的材料,但並不限定於該等。
上述酸產生劑可單獨使用1種或將2種以上組合使用。添加酸產生劑時的添加量,相對於前述化合物(A)100質量份宜為0.05~50質量份,更佳為0.1~10質量份。
本發明之有機膜形成用組成物中,為了改善旋塗時之塗布性,可添加(D)界面活性劑。就界面活性劑而言,例如可使用日本特開2009-269953號公報中之段落(0142)~(0147)記載者。
又,本發明之有機膜形成用組成物中,為了提高硬化性,進一步抑制和上層膜之交叉混合,亦可添加(E)交聯劑。交聯劑並無特別限定,可廣泛使用公知的各類型的交聯劑。就一例而言,可例示三聚氰胺系交聯劑、甘脲系交聯劑、苯并胍胺系交聯劑、脲系交聯劑、β-羥基烷基醯胺系交聯劑、異氰尿酸酯系交聯劑、氮丙啶系交聯劑、㗁唑啉系交聯劑、環氧系交聯劑。
作為三聚氰胺系交聯劑,具體而言可例示六甲氧基甲基化三聚氰胺、六丁氧基甲基化三聚氰胺、它們的烷氧基及/或羥基取代體、及它們的部分自縮合物。作為甘脲系交聯劑,具體而言可例示四甲氧基甲基化甘脲、四丁氧基甲基化甘脲、它們的烷氧基及/或羥基取代體、及它們的部分自縮合物。作為苯并胍胺系交聯劑,具體而言可例示四甲氧基甲基化苯并胍胺、四丁氧基甲基化苯并胍胺、它們的烷氧基及/或羥基取代體、及它們的部分自縮合物。作為脲系交聯劑,具體而言可例示二甲氧基甲基化二甲氧基伸乙基脲、其烷氧基及/或羥基取代體、及它們的部分自縮合物。作為β-羥基烷基醯胺系交聯劑,具體而言可例示N,N,N’,N’-四(2-羥基乙基)己二醯胺。作為異氰尿酸酯系交聯劑,具體而言可例示異氰尿酸三環氧丙酯、異氰尿酸三烯丙酯。作為氮丙啶系交聯劑,具體而言可例示4,4’-雙(伸乙基亞胺基羰基胺基)二苯基甲烷、參[3-(1-氮丙啶基)丙酸-2,2-雙羥基甲基丁酯]。作為㗁唑啉系交聯劑,具體而言可例示2,2’-異亞丙基雙(4-苄基-2-㗁唑啉)、2,2’-異亞丙基雙(4-苯基-2-㗁唑啉)、2,2’-亞甲基雙-4,5-二苯基-2-㗁唑啉、2,2’-亞甲基雙-4-苯基-2-㗁唑啉、2,2’-亞甲基雙-4-第三丁基-2-㗁唑啉、2,2’-雙(2-㗁唑啉)、1,3-伸苯基雙(2-㗁唑啉)、1,4-伸苯基雙(2-㗁唑啉)、2-異丙烯基㗁唑啉共聚物。作為環氧系交聯劑,具體而言可例示二環氧丙醚、乙二醇二環氧丙醚、1,4-丁烷二醇二環氧丙醚、1,4-環己烷二甲醇二環氧丙醚、聚(甲基丙烯酸環氧丙酯)、三羥甲基乙烷三環氧丙醚、三羥甲基丙烷三環氧丙醚、新戊四醇四環氧丙醚。
又,本發明之有機膜形成用組成物中,為了進一步改善平坦化/填埋特性,可添加(F)塑化劑。塑化劑並無特別限定,可廣泛使用公知的各種類型的塑化劑。就一例而言,可例示苯二甲酸酯類、己二酸酯類、磷酸酯類、偏苯三甲酸酯類、檸檬酸酯類等低分子化合物、聚醚系、聚酯系、日本特開2013-253227記載之聚縮醛系聚合物等聚合物。
又,本發明之有機膜形成用組成物中,就用以和塑化劑一樣賦予填埋/平坦化特性之添加劑而言,例如可理想地使用具有聚乙二醇、聚丙二醇結構之液狀添加劑、或從30℃至250℃之間之重量減少率為40質量%以上且重量平均分子量為300~200,000的熱分解性聚合物。該熱分解性聚合物宜為含有具下列通式(DP1)、(DP1a)表示之縮醛結構的重複單元者。
如上,本發明之有機膜形成用組成物,係會形成具有良好乾蝕刻耐性,且兼具400℃以上之耐熱性及高程度填埋/平坦化特性的有機膜者。因此,作為2層光阻法、使用了含矽光阻中間膜或含矽無機硬遮罩的3層光阻法、使用了含矽光阻中間膜或含矽無機硬遮罩及有機抗反射膜的4層光阻法等多層光阻法所使用的有機下層膜之形成材料係極為有用。又,本發明之有機膜形成用組成物,即使於鈍性氣體中成膜亦不會產生副產物,具有優異的填埋/平坦化特性,故也可理想地用作多層光阻法以外的半導體裝置製造步驟中之平坦化材料。
<有機膜形成方法>
用以形成有機膜之加熱成膜步驟,可採用1段烘烤、2段烘烤或3段以上之多段烘烤,1段烘烤或2段烘烤在經濟方面較理想。利用1段烘烤所為之成膜係於100℃以上600℃以下之溫度以5~3600秒之範圍進行,尤其宜於150℃以上500℃以下之溫度以10~7200秒之範圍進行。藉由以如此之條件進行熱處理,可促進因熱流動所獲致之平坦化與交聯反應。多層光阻法有時會於該獲得的膜之上形成塗布型矽中間膜、CVD硬遮罩。使用塗布型矽中間膜時,宜在比起將矽中間膜成膜之溫度更高的溫度將有機下層膜予以成膜。通常,矽中間膜宜在100℃以上400℃以下,宜為150℃以上350℃以下成膜。在比起該溫度更高的溫度將有機下層膜予以成膜的話,可防止由於矽中間膜形成用組成物導致有機下層膜溶解,可形成不會與該組成物混合的有機膜。又,在矽中間膜形成過程中不會有有機下層膜發生熱分解而產生副產物之虞。
使用CVD硬遮罩時,宜在比起形成CVD硬遮罩之溫度更高的溫度將有機下層膜予以成膜。形成CVD硬遮罩之溫度,可例示150℃以上500℃以下之溫度。
另一方面,在利用2段烘烤所為之成膜中,於空氣中進行第1段烘烤的情況,當可能會因氧而導致發生基板的腐蝕時,於空氣中之處理溫度的上限為300℃以下,宜於250℃以下以10~600秒之範圍進行。於鈍性氣體中之第2段的烘烤溫度宜比起第1段的烘烤溫度更高,於600℃以下,較佳為於500℃以下之溫度以10~7200秒之範圍進行。
又,本發明之有機膜形成用組成物可使用於係作為半導體裝置之製造步驟中使用之有機下層膜發揮功能的有機膜之形成方法,且為了防止被加工基板的腐蝕,而將被加工基板於氧濃度1%以下之氣體環境進行熱處理以形成硬化膜的有機膜形成方法。
該有機膜形成方法中,首先將上述本發明之有機膜形成用組成物旋轉塗布於被加工基板上。旋轉塗布後,於2段烘烤中,首先在空氣中、300℃以下烘烤後,於氧濃度1%以下之氣體環境進行第2段烘烤。1段烘烤的情況,將初始的第1段之在空氣中之烘烤省略即可。此外,烘烤中之氣體環境可例示氮氣、氬氣、氦氣等鈍性氣體。若為本發明之材料,則即使在如此之鈍性氣體環境中加熱,亦可形成充分硬化的有機膜,而不會產生昇華物。
又,上述有機膜形成方法可使用於具有高度30nm以上之結構體或高低差的被加工基板。如上述,本發明之有機膜形成用組成物,由於填埋/平坦化特性優異,故即使被加工基板有高度30nm以上之結構體或高低差(凹凸),仍可形成平坦的硬化膜。亦即,本發明之有機膜形成方法對於在如此之被加工基板上形成平坦的有機膜的情形係特別有用。
此外,所形成之有機膜的厚度可適當選擇,宜為30~20,000nm,尤其宜為50~15,000nm。
又,於使用本發明之有機膜形成用組成物形成成為多層光阻法之下層膜的有機膜的情形、及形成平坦化膜用之有機膜的情形,兩者皆可採用上述有機膜形成方法。
本發明之有機膜形成用組成物,可使用於能使半導體裝置之製造步驟中使用之高低差基板之表面平坦化的有機膜之形成,並可應用於如下之有機膜形成方法:於被加工基板上旋轉塗布本發明之有機膜形成用組成物,將塗布有該有機膜形成用組成物之基板,以50℃以上250℃以下之溫度並以10~600秒之範圍在空氣中進行熱處理,然後,在鈍性氣體中以250℃以上之溫度進行10~7200秒的熱處理,藉此形成硬化膜。
該有機膜形成方法中,首先,將上述本發明之有機膜形成用組成物旋轉塗布於被加工基板上。藉由使用旋轉塗布法,可確實地獲得良好的填埋特性。旋轉塗布後,為了促進因熱流動所獲致之平坦化與交聯反應,實施烘烤(熱處理)。此外,藉由該烘烤,可使組成物中之溶劑蒸發,故即使在有機膜上形成光阻上層膜、含矽光阻中間膜時,亦能防止混合。
<圖案形成方法>
[使用了含矽光阻中間膜的3層光阻法]
本發明可採用一種圖案形成方法,係在被加工基板上使用本發明之有機膜形成用組成物形成有機膜,在該有機膜之上使用含有矽原子之膜形成材料形成含矽膜,於該含矽膜之上使用由光阻組成物構成之光阻上層膜材料形成光阻上層膜,於該光阻上層膜形成電路圖案,以該形成有電路圖案之光阻上層膜作為遮罩並利用蝕刻將圖案轉印至前述含矽膜,以該轉印有圖案之含矽膜作為遮罩並利用蝕刻將圖案轉印至前述有機膜,再以該轉印有圖案之有機膜作為遮罩並利用蝕刻將圖案轉印至前述被加工基板。
就被加工基板而言,宜使用半導體裝置基板、或在該半導體裝置基板上成膜有金屬膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜、及金屬氧化氮化膜中之任一種者,更具體而言,可使用Si、α-Si、p-Si、SiO2
、SiN、SiON、W、TiN、Al等基板、在該基板上成膜有上述金屬膜等作為被加工層者,並無特別限定。
被加工層可使用Si、SiO2
、SiON、SiN、p-Si、α-Si、W、W-Si、Al、Cu、Al-Si等各種Low-k膜及其阻擋膜,通常可形成50~10,000nm,尤其100~5,000nm之厚度。又,將被加工層成膜時,基板與被加工層係使用不同材質者。
此外,構成被加工基板之金屬,宜為矽、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、鋁、銦、鎵、砷、鈀、鐵、鉭、銥、鈷、錳、鉬、或它們的合金。
又,被加工基板宜使用具有高度30nm以上之結構體或高低差的被加工基板。
在被加工基板上使用本發明之有機膜形成用組成物形成有機膜時,可採用上述有機膜形成方法。
然後,於有機膜之上使用含有矽原子之光阻中間膜材料形成光阻中間膜(含矽光阻中間膜)。含矽光阻中間膜材料宜為聚矽氧烷系之中間膜材料。藉由使含矽光阻中間膜帶有抗反射效果,可抑制反射。尤其就193nm曝光用途而言,使用含有多數芳香族且和基板之蝕刻選擇性高之材料作為有機膜形成用組成物的話,k値增高,基板反射變高,但藉由使含矽光阻中間膜帶有會成為適當k値之吸收,可抑制反射,能使基板反射成為0.5%以下。作為有抗反射效果的含矽光阻中間膜,248nm、157nm曝光用途可理想地使用懸垂結構或聚矽氧烷結構中具有蒽,193nm曝光用途可理想地使用懸垂結構或聚矽氧烷結構中具有含苯基或矽-矽鍵之吸光基且會因酸或熱而交聯的聚矽氧烷。
然後,於含矽光阻中間膜之上使用由光阻組成物構成之光阻上層膜材料形成光阻上層膜。光阻上層膜材料可為正型也可為負型,可使用和通常使用之光阻組成物相同者。宜將光阻上層膜材料旋轉塗布後,於60~180℃以10~300秒之範圍進行預烘。之後,依常法進行曝光,進一步進行曝光後烘烤(PEB)、顯影,獲得光阻上層膜圖案。此外,光阻上層膜的厚度並無特別限制,宜為30~500nm,尤其宜為50~400nm。
然後,在光阻上層膜形成電路圖案(光阻上層膜圖案)。電路圖案之形成,宜利用使用了波長為10nm以上300nm以下之光之微影、利用電子束所為之直接描繪、奈米壓模、或該等之組合來形成電路圖案。
此外,曝光光可列舉波長300nm以下之高能射線,具體而言可列舉遠紫外線、KrF準分子雷射光(248nm)、ArF準分子雷射光(193nm)、F2
雷射光(157nm)、Kr2
雷射光(146nm)、Ar2
雷射光(126nm)、3~20nm之軟X射線(EUV)、電子束(EB)、離子束、X射線等。
又,電路圖案之形成,宜利用鹼顯影或有機溶劑顯影將電路圖案進行顯影。
然後,以形成有電路圖案之光阻上層膜作為遮罩,利用蝕刻將圖案轉印至含矽光阻中間膜。以光阻上層膜圖案作為遮罩而進行之含矽光阻中間膜的蝕刻,宜使用氟碳系之氣體進行。藉此,形成含矽光阻中間膜圖案。
然後,以轉印有圖案之含矽光阻中間膜作為遮罩,利用蝕刻將圖案轉印至有機膜。含矽光阻中間膜對於氧氣或氫氣,相較於有機物顯示較高的蝕刻耐性,故以含矽光阻中間膜圖案作為遮罩而進行之有機膜的蝕刻,宜使用以氧氣或氫氣為主體之蝕刻氣體進行。藉此,可形成有機膜圖案。
然後,以轉印有圖案之有機膜作為遮罩,利用蝕刻將圖案轉印至被加工基板。之後的被加工基板(被加工層)之蝕刻,可依常法進行,例如被加工基板若為SiO2
、SiN、二氧化矽系低介電常數絕緣膜,則進行以氟龍(flon)系氣體為主體之蝕刻,若為p-Si、Al、W,則進行以氯系、溴系氣體為主體之蝕刻。基板加工係利用以氟龍系氣體所為之蝕刻進行時,含矽光阻中間膜圖案會在基板加工的同時被剝離。另一方面,基板加工係利用以氯系、溴系氣體所為之蝕刻進行時,為了將含矽光阻中間膜圖案予以剝離,需於基板加工後另外進行以氟龍系氣體所為之乾蝕刻剝離。
使用本發明之有機膜形成用組成物獲得之有機膜,係如上述之被加工基板之蝕刻時的蝕刻耐性優異者。
[使用了含矽光阻中間膜與有機抗反射膜的4層光阻法]
又,本發明亦可採用一種圖案形成方法,係在被加工基板上使用本發明之有機膜形成用組成物形成有機膜,在該有機膜之上使用含有矽原子之光阻中間膜材料形成含矽光阻中間膜,於該含矽光阻中間膜之上形成有機抗反射膜,於該有機抗反射膜上使用由光阻組成物構成之光阻上層膜材料形成光阻上層膜,於該光阻上層膜形成電路圖案,以該形成有電路圖案之光阻上層膜作為遮罩並利用乾蝕刻將圖案轉印至前述有機抗反射膜與前述含矽光阻中間膜,以該轉印有圖案之含矽光阻中間膜作為遮罩並利用蝕刻將圖案轉印至前述有機膜,再以該轉印有圖案之有機膜作為遮罩並利用蝕刻將圖案轉印至前述被加工基板。
又,該方法除了在含矽光阻中間膜與光阻上層膜之間形成有機抗反射膜(BARC)以外,可和上述使用了含矽光阻中間膜的3層光阻法同樣進行。
有機抗反射膜可使用公知的有機抗反射膜材料並利用旋轉塗布形成。
[使用了無機硬遮罩的3層光阻法]
又,作為使用了本發明之有機膜形成用組成物的3層光阻法所為之圖案形成方法,本發明亦可採用一種圖案形成方法,係在被加工基板上使用上述本發明之有機膜形成用組成物形成有機膜,在該有機膜之上形成選自矽氧化膜、矽氮化膜、矽氧化氮化膜、鈦氧化膜、及鈦氮化膜之無機硬遮罩,於該無機硬遮罩之上使用由光阻組成物構成之光阻上層膜材料形成光阻上層膜,於該光阻上層膜形成電路圖案,以該形成有電路圖案之光阻上層膜作為遮罩並利用蝕刻將圖案轉印至前述無機硬遮罩,以該轉印有圖案之無機硬遮罩作為遮罩並利用蝕刻將圖案轉印至前述有機膜,再以該轉印有圖案之有機膜作為遮罩並利用蝕刻將圖案轉印至前述被加工基板。
又,該方法除了於有機膜之上形成無機硬遮罩以替代含矽光阻中間膜以外,可和上述使用了含矽光阻中間膜的3層光阻法同樣進行。
選自矽氧化膜、矽氮化膜、及矽氧化氮化膜(SiON膜)之無機硬遮罩,可利用CVD法、ALD法等形成。矽氮化膜之形成方法,例如記載於日本特開2002-334869號公報、國際公開第2004/066377號公報等。無機硬遮罩之膜厚宜為5~200nm,更佳為10~100nm。無機硬遮罩宜使用作為抗反射膜之效果高的SiON膜最佳。形成SiON膜時的基板溫度為300~500℃,故下層膜需耐受300~500℃之溫度。使用本發明之有機膜形成用組成物所形成的有機膜具有高耐熱性,能夠耐受300℃~500℃之高溫,故可為利用CVD法或ALD法形成之無機硬遮罩、及利用旋轉塗布法形成之有機膜的組合。
[使用了無機硬遮罩與有機抗反射膜的4層光阻法]
又,作為使用了本發明之有機膜形成用組成物的4層光阻法所為之圖案形成方法,本發明亦可採用一種圖案形成方法,係在被加工基板上使用上述本發明之有機膜形成用組成物形成有機膜,在該有機膜之上形成選自矽氧化膜、矽氮化膜、及矽氧化氮化膜之無機硬遮罩,於該無機硬遮罩之上形成有機抗反射膜,於該有機抗反射膜上使用由光阻組成物構成之光阻上層膜材料形成光阻上層膜,於該光阻上層膜形成電路圖案,以該形成有電路圖案之光阻上層膜作為遮罩並利用蝕刻將圖案轉印至前述有機抗反射膜與前述無機硬遮罩,以該轉印有圖案之無機硬遮罩作為遮罩並利用蝕刻將圖案轉印至前述有機膜,再以該轉印有圖案之有機膜作為遮罩並利用蝕刻將圖案轉印至前述被加工基板。
此外,該方法除了在無機硬遮罩與光阻上層膜之間形成有機抗反射膜(BARC)以外,可和上述使用了無機硬遮罩的3層光阻法同樣進行。
尤其使用SiON膜作為無機硬遮罩時,藉由SiON膜與BARC之2層抗反射膜,在超過1.0之高NA之浸潤曝光中仍可抑制反射。形成BARC之另一優點,係具有減少在SiON膜正上方之光阻上層膜圖案之拖尾的效果。
此處,利用3層光阻法所為之圖案形成方法之一例示於圖2(A)~(F)。3層光阻法的情況,如圖2(A)所示般,在形成於基板1之上的被加工層2上使用本發明之有機膜形成用組成物形成有機膜3後,形成含矽光阻中間膜4,並於其上形成光阻上層膜5。然後,如圖2(B)所示般,將光阻上層膜5之曝光部分6進行曝光,並進行PEB(曝光後烘烤)。然後,如圖2(C)所示般,進行顯影而形成光阻上層膜圖案5a。然後,如圖2(D)所示般,以光阻上層膜圖案5a作為遮罩,使用氟龍系氣體將含矽光阻中間膜4進行乾蝕刻加工,形成含矽光阻中間膜圖案4a。然後,如圖2(E)所示般,除去光阻上層膜圖案5a後,以含矽光阻中間膜圖案4a作為遮罩,將有機膜3進行氧電漿蝕刻,形成有機膜圖案3a。然後,如圖2(F)所示般,除去含矽光阻中間膜圖案4a後,以有機膜圖案3a作為遮罩,對被加工層2進行蝕刻加工,形成圖案2a。
形成無機硬遮罩時,將含矽光阻中間膜4變更為無機硬遮罩即可,形成BARC時,在含矽光阻中間膜4與光阻上層膜5之間形成BARC即可。BARC的蝕刻,可在含矽光阻中間膜4的蝕刻之前連續進行,也可僅進行BARC之蝕刻後,改變蝕刻裝置等再進行含矽光阻中間膜4的蝕刻。
如上述,若為本發明之圖案形成方法,可利用多層光阻法在被加工基板以高精度形成微細的圖案。
[實施例]
以下,舉合成例、比較合成例、實施例、及比較例對本發明進行更具體地說明,但本發明並不限定於該等。此外,就分子量及分散度而言,係求出利用以四氫呋喃作為洗提液之凝膠滲透層析(GPC)得到的聚苯乙烯換算之重量平均分子量(Mw)、數量平均分子量(Mn),並求出分散度(Mw/Mn)。
合成例 高耐熱有機化合物之合成
[合成例1]化合物(A1)之合成
[化35]
將二醇(B1)7.7g、碳酸鉀3.0g、N,N-二甲基甲醯胺40g予以混合,升溫至55℃。緩慢滴加1-溴-2-丁炔2.9g,於55℃加熱攪拌20小時。冷卻至室溫後,加入甲基異丁基酮150g,進行水洗、減壓濃縮後,加入甲醇,濾取生成的固體,進行甲醇洗淨、減壓乾燥,得到目的物(A1)8.7g。合成得到的化合物(A1)之IR、1
H NMR分析結果如下所示。
IR(D-ATR):
ν=3057、3029、2954、2916、2867、1601、1494、1476、1446、1217、1005、819cm-1
。1
H NMR(600 MHz, DMSO-d6
) δ7.94(d, J=7.3Hz,4H)、7.71(d, J=9.2Hz, 2H)、7.60(d, J=9.2Hz, 2H)、7.51-7.45(m, 10H)、7.41-7.38(m, 4H)、7.31-7.28(m, 6H)、7.28-7.15(m, 6H)、7.08-7.06(m, 2H)、4.80(d, J=2.3Hz, 4H)、1.79(dd, J=2.3, 2.3Hz, 6H)。
利用GPC求出重量平均分子量(Mw)、分散度(Mw/Mn),結果如下。
(A1):Mw=1000、Mw/Mn=1.23。
[合成例2]化合物(A1)之合成
[化36]
將二醇(B1)7.7g、碳酸鉀3.0g、N,N-二甲基甲醯胺40g予以混合,升溫至55℃。緩慢滴加溴丙炔80%甲苯溶液3.3g,於55℃加熱攪拌14小時。冷卻至室溫後,加入甲苯150g,進行水洗、減壓濃縮,得到炔丙基體(B2)8.4g。
然後,於N2
環境下在冷卻至-30℃的炔丙基體(B2)8.4g與四氫呋喃60mL之混合液中,加入正丁基鋰2.65M己烷溶液10mL,於-30℃攪拌1小時。加入硫酸二甲酯4.4g,緩慢升溫至室溫,升溫60℃並攪拌6小時。冷卻至室溫後,加入稀鹽酸使反應停止。加入甲基異丁基酮100g,進行水洗、減壓濃縮後,加入甲醇,濾取生成的固體,進行甲醇洗淨、減壓乾燥,得到目的物(A1)8.5g。合成得到的化合物(A1)之IR、1
H NMR分析結果如下所示。
IR(D-ATR):
ν=3058、3029、2954、2917、2868、1602、1494、1477、1446、1218、1005、819cm-1
。1
H NMR(600MHz, DMSO-d6
) δ7.94(d, J=7.3Hz, 4H)、7.71(d, J=9.2Hz, 2H)、7.60(d, J=9.2Hz, 2H)、7.51-7.45(m, 10H)、7.41-7.38(m, 4H)、7.31-7.28(m, 6H)、7.28-7.15(m, 6H)、7.08-7.06(m, 2H)、4.80(d, J=2.3Hz, 4H)、1.79(dd, J=2.3, 2.3Hz, 6H)。
利用GPC求出重量平均分子量(Mw)、分散度(Mw/Mn),結果如下。
(A1):Mw=1000、Mw/Mn=1.32。
[合成例3]化合物(A2)之合成
將4,4’-二羥基二苯甲酮8.78g、丙酮50mL予以混合,加入碳酸鉀17g,進一步滴加1-溴-2-丁炔7.9mL。將反應混合物加熱,徹夜加熱回流。冷卻至室溫後,進行過濾,將濾液減壓濃縮後,加入甲醇:氯仿=9:1之混合溶劑,濾取生成的固體,得到下列所示之中間體(B3)10.6g。合成得到的中間體(B3)之1
H NMR分析結果如下所示。
1
H NMR(400 MHz, CDCl3
) δ7.81(d, Ar-H, 4H)、7.05(d, Ar-H, 4H)、4.75(s, CH2
, 4H)、1.90(s, CH3
, 6H)。
然後,於N2
環境下在冷卻至-70℃的4,4’-二溴聯苯5.44g與四氫呋喃50mL之混合液中,加入正丁基鋰1.6M己烷溶液23.92mL,在-40℃攪拌1小時。滴加溶解於四氫呋喃50mL之中間體(B3)12.18g,緩慢升溫至室溫,在室溫徹夜攪拌。加入14%氯化銨水溶液100mL使反應停止。加入乙酸乙酯200mL,進行水洗、減壓濃縮後,加入二氯甲烷:戊烷=1:3混合液,冷卻至0~5℃,濾取生成的固體,進行戊烷洗淨、減壓乾燥,得到8.7g的下列所示之化合物(A2)。合成得到的化合物(A2)之1
H NMR分析結果如下所示。
1
H NMR(400 MHz, CDCl3
) δ7.55(d, Ar-H, 4H)、7.35(d, Ar-H, 4H)、7.23(d, Ar-H, 8H)、6.93(d, Ar-H, 8H)、4.66(s, CH2
, 8H)、1.88(s, CH3
, 12H)。
[合成例4]化合物(A3)之合成
於N2
環境下將2-氯菸鹼酸乙酯25g、苯基硼酸21.04g、肆(三苯基膦)鈀(0)3g、碳酸鉀55.1g、四氫呋喃:水=1:1混合液250mL予以混合,於加熱回流下徹夜攪拌。冷卻至室溫後,加入乙酸乙酯200mL,除去水層並以蒸餾水(2×100mL)洗淨。將獲得之有機層利用硫酸鎂乾燥,並進行減壓濃縮。將獲得之油狀物質利用二氧化矽進行過濾,並溶解於甲醇150mL。在該溶液中加入氫氧化鈉10.8g,於室溫攪拌6小時。將反應溶液減壓濃縮,以水稀釋獲得之白色固體,加入1M鹽酸以成為pH=4~5。分濾生成的白色結晶,得到下列化合物(B4)。將獲得之水層以乙酸乙酯(2×100mL)萃取,利用硫酸鎂乾燥有機層後,進行過濾、減壓濃縮,得到剩餘的化合物(B4)。化合物(B4)合計得到21.46g。合成得到的中間體化合物(B4)之1
H NMR分析結果如下所示。
1
H NMR(400MHz, DMSO-d6
) δ(ppm): 13.31(bs, COO-H, 1H)、8.76(d, Ar-H, 1H)、8.11(d, Ar-H, 1H)、7.58(m, Ar-H, 3H)、7.46(m, Ar-H, 3H)。
然後,於N2
環境下在安裝有溫度計之三口燒瓶中加入加熱至80℃的聚磷酸(相對於化合物(B4)為25%的量),然後滴加化合物(B4)9.96g,於210℃劇烈攪拌3小時。將反應液冷卻至60~70℃後,加入1M氫氧化鈉水溶液以成為pH=10並使反應停止。濾取生成的固體,進行蒸餾水洗淨、減壓乾燥,得到化合物(B5)9.05g。合成得到的化合物(B5)之1
H NMR分析結果如下所示。
1
H NMR(400MHz, CDCl3
) δ(ppm):8.64(d, Ar-H, 1H)、7.92(m, Ar-H, 2H)、7.76(d, Ar-H, 1H)、7.64(t, Ar-H, 1H)、7.47(t, Ar-H, 1H)、7.25(m, Ar-H, 1H)。
然後,於N2
環境下在冷卻至-70℃的4,4’-二溴聯苯2.38g與四氫呋喃50mL之混合液中,加入正丁基鋰1.6M己烷溶液10.45mL,在-40℃攪拌1小時。加入化合物(B5)500mg,緩慢升溫至室溫,於室溫徹夜攪拌。加入14%氯化銨水溶液50mL使反應停止。除去水層,將有機層進行減壓濃縮,然後加入二氯甲烷,冷卻至0~5℃並劇烈攪拌。濾取生成的固體,進行甲醇洗淨、減壓乾燥,得到二醇(B6)2.2g。合成得到的化合物(B6)之1
H NMR、MALDI-TOF MS分析結果如下所示。
[化41]
1
H NMR(400MHz, DMSO-d6
) δ(ppm):8.53(d, Ar-H, 2H)、7.87(d, Ar-H, 2H)、7.65(d, Ar-H, 2H)、7.51-7.45(m, Ar-H, 6H)、7.42-7.38(m, Ar-H, 4H)、7.34(d, Ar-H, 4H)、7.26-7.23(m, Ar-H, 2H)、6.60(bs, OH, 2H)。MALDI-TOF MS m/z(+ve):498[M-OH]+
。
然後,將化合物(B6)500mg、2-萘酚307mg、乙酸18mL予以混合。在該懸浮液中加入甲磺酸2mL,進行N2
置換後,加熱回流16小時。冷卻至室溫後,加入飽和碳酸氫鈉水溶液(100mL),以乙酸乙酯(2×50mL)萃取。將有機層以蒸餾水(2×50mL)洗淨,利用硫酸鎂乾燥後,進行過濾、減壓濃縮,然後加入乙醇,在0~5℃攪拌1小時。濾取生成的固體,進行乙醇洗淨、減壓乾燥,得到化合物(B7)320mg。合成得到的化合物(B7)之1
H NMR、MALDI-TOF MS分析結果如下所示。
[化42]
1
H NMR(400MHz,DMF-d7
) δ(ppm):9.76(bs, OH, 2H)、8.60(s, Ar-H, 2H)、8.02(d, Ar-H, 2H)、7.80(m, Ar-H, 2H)、7.69-7.13 (m, Ar-H, 26H)、7.12-6.95(m, Ar-H, 2H)。MALDI-TOF MS m/z(+ve):768[M-H]+
。
然後,將化合物(B7)200mg、溴丙炔74mg、碳酸鉀108mg、N,N-二甲基甲醯胺10mL予以混合,升溫至80℃並加熱攪拌24小時。冷卻至室溫後,加入乙酸乙酯60mL,以飽和氯化鈉水溶液(2×50mL)、蒸餾水(2×50mL)洗淨。利用硫酸鎂乾燥後,進行過濾、減壓濃縮,然後加入己烷200mL,冷卻至0~5℃並攪拌1小時。濾取生成的固體,進行己烷洗淨、減壓乾燥,得到化合物(B8)181mg。合成得到的化合物(B8)之1
H NMR、MALDI-TOF MS分析結果如下所示。
1
H NMR(400 MHz, DMSO-d6
) δ(ppm): 8.60 (s, Ar-H, 2H)、8.04 (d, Ar-H, 2H)、7.94-6.94 (m, Ar-H, 30H)、4.88 (s, CH2
, 4H)、3.58 (s, CH, 2H)。MALDI-TOF MS m/z (+ve): 845 [M-H]+
。
於N2
環境下在冷卻至-60~-70℃的化合物(B8)100mg與四氫呋喃10mL之混合液中,加入正丁基鋰1.6M己烷溶液0.162mL,在-50~-40℃攪拌1小時。將反應液冷卻至-60~-70℃後,加入甲基碘0.022mL,緩慢升溫至室溫,於室溫徹夜攪拌。冷卻後加入乙酸乙酯30mL,以飽和氯化鈉水溶液(2×25mL)、蒸餾水(2×25mL)洗淨。利用硫酸鎂乾燥後,進行過濾、減壓濃縮,然後加入己烷100mL,冷卻至0~5℃並攪拌1小時。濾取生成的固體,進行己烷洗淨、減壓乾燥,得到目的物(A3)83mg。合成得到的化合物(A3)之1
H NMR、MALDI-TOF MS分析結果如下所示。
[化44]
1
H NMR(400 MHz, DMSO-d6
) δ(ppm):8.62(s, Ar-H, 2H)、8.04(d, Ar-H, 2H)、7.94-6.94(m, Ar-H, 30H)、4.87(s, CH2
, 4H)、1.77(s, CH3
, 6H)。MALDI-TOF MS m/z(+ve): 873 [M-H]+
。
利用GPC求出重量平均分子量(Mw)、分散度(Mw/Mn),結果如下。
(A3):Mw=500、Mw/Mn=1.14。
比較合成例 有機化合物之合成
[比較合成例1]化合物(A4)之合成
將二醇(B1)7.7g、碳酸鉀3.0g、N,N-二甲基甲醯胺40g予以混合,升溫至55℃。緩慢滴加溴丙炔80%甲苯溶液3.3g,於55℃加熱攪拌14小時。冷卻至室溫後,加入甲苯150g,進行水洗、減壓濃縮,得到炔丙基體(A4)8.4g。
[比較合成例2]化合物(A5)之合成
將9,9-亞茀基-雙萘酚90.1g、37%福馬林水溶液10.5g、及2-甲氧基-1-丙醇270g,在氮氣環境下、內溫80℃製成均勻溶液,然後緩慢加入20%對甲苯磺酸2-甲氧基-1-丙醇溶液18g,於內溫110℃攪拌8小時。冷卻至室溫後,加入甲基異丁基酮600g,將有機層以純水200g洗淨5次後,對有機層進行減壓乾固。在殘渣中加入THF400ml,以己烷2,000ml使聚合物再沉澱。過濾分離沉降的聚合物,進行減壓乾燥,得到化合物(A5)。
[化46]
利用GPC求出重量平均分子量(Mw)、分散度(Mw/Mn),結果如下。
(A5):Mw=3700、Mw/Mn=2.82。
[比較合成例3]化合物(A6)之合成
於氮氣環境下,在稱量有鎂26.4g(1.09mol)之5L的4口燒瓶內,加入預先以脫水THF(四氫呋喃)1,000ml溶解之4,4’-二溴聯苯168g(0.54mol)、氯化鋰23.0g (0.54mol)至浸漬鎂的程度。加入少量的二溴乙烷,使反應開始後,於維持發熱的狀態歷時3小時滴加剩餘的THF溶液。滴加結束後,加入THF500ml,於回流下熟成8小時,製備Grignard試劑。冷卻至內溫55℃後,歷時2小時滴加預先溶解於脫水THF400ml的9-茀酮150g(0.83mol)。滴加結束後,於回流下熟成5小時半,在冰浴中冷卻燒瓶,並利用飽和氯化銨水溶液1,000ml與純水1,000ml淬滅反應。此時,溶液生成白色的析出物而成為懸浮液。在反應溶液中追加MIBK(甲基異丁基酮)150ml,將懸浮液直接轉移至分液漏斗,取出水層,進一步利用純水500ml進行分液水洗,然後,將有機層進行減壓濃縮。以二異丙醚進行再結晶,分濾生成的白色結晶並乾燥,藉此,以產率51.0%得到聯苯衍生物(B9)109g。
[化47]
聯苯衍生物(B9):
IR(D-ATR):ν=3539、3064、3039、1605、1495、1447、1164、1030、909、820、771、754、736cm-1
。1
H-NMR(600MHz inDMSO-d6
):δ=6.34(2H, -OH, s)、7.24(4H, t)、7.27(8H, d)、7.36(4H, t-t)、7.45(4H, d)、7.81(4H, d)ppm。13
C-NMR(150MHz inDMSO-d6
):δ=82.44、120.10、124.66、125.66、126.28、128.07、128.51、138.41、139.14、144.19、151.23ppm。
然後,將聯苯衍生物(B9)40.3g(78.4mmol)、2-萘酚23.73g(164.6mmol)、1,2-二氯乙烷240ml稱量至1L的3口燒瓶。在30℃之油浴中邊攪拌邊緩慢滴加甲磺酸7.3ml。滴加結束後使油浴之溫度上升至50℃,進行6小時反應。放冷至室溫後,以MIBK500ml稀釋,分濾不溶成分並轉移至分液漏斗,利用300ml的超純水重複分液水洗9次。將有機層進行減壓濃縮,在殘渣中加入THF 800ml並且使其溶解,然後,以己烷2,500ml進行結晶後,分濾結晶並乾燥,藉此,以產率85.8%得到聯苯衍生物化合物(A6)51.6g。
[化48]
化合物(A6):
IR(KBr):ν=3528、3389、3059、3030、1633、1604、1506、1493、1446、1219、1181、750、740cm-1
。1
H-NMR(600MHz inDMSO-d6
):δ=6.98(2H, d-d)、7.05(2H, s-d)、7.17(4H, d)、7.24(2H, d-d)、7.29(4H, t)、7.38(4H, t)、7.40(2H, s)、7.45(4H, d)、7.50(6H, d)、7.58(2H, d)、7.93(4H, d)、9.72(2H, -OH, s)ppm。13
C-NMR(150MHz inDMSO-d6
):δ=64.59、108.35、118.77、120.58、125.19、126.11、126.36、126.62、126.94、127.16、127.71、127.88、128.20、129.35、133.39、138.14、139.26、139.59、144.82、150.56、155.39ppm。
有機膜形成用組成物(UDL-1~5、比較UDL1~4)之製備
將上述化合物(A1)~(A6)、作為添加劑之交聯劑(CR1)、酸產生劑(AG1)、溶劑(S1)1,6-二乙醯氧基己烷(沸點260℃)、或(S2)三丙二醇單甲醚(沸點242℃),以表1所示之比例溶解於含有丙二醇單甲醚乙酸酯(PGMEA)、FC-4430(住友3M(股)製)0.1質量%的溶劑中,利用0.1μm之氟樹脂製的過濾器進行過濾,藉此,分別製備有機膜形成用組成物(UDL-1~5、比較UDL-1~4)。
實施例1 於氮氣環境中烘烤之溶劑耐性測定(實施例1-1~1-5、比較例1-1~1-4)
將上述製備得到的有機膜形成用組成物(UDL-1~5、比較UDL-1~4)塗布於矽基板上,在氧濃度管理為0.2%以下之氮氣流下,於400℃煅燒60秒後,測定膜厚,於其上分配PGMEA溶劑,放置30秒並旋乾,於100℃烘烤60秒,使PGMEA蒸發,測定膜厚並求出PGMEA處理前後之膜厚差。
如表2所示,本發明之有機膜形成用組成物(實施例1-1~1-5)經PGMEA處理後之殘膜率為99%以上,可知即使於氮氣環境下,亦會發生交聯反應,並展現充分的溶劑耐性。反觀未添加交聯劑與熱酸產生劑的比較例1-2、1-3中,PGMEA處理後之殘膜率未達50%,未展現充分的溶劑耐性,為了展現充分的溶劑耐性需添加交聯劑及熱酸產生劑。由該結果可知,上述通式(1-1)中之(A-碳碳參鍵-Y)表示之次結構於氮氣環境下發生熱硬化反應,並展現溶劑耐性。
實施例2 於大氣中烘烤之溶劑耐性測定(實施例2-1~2-5、比較例2-1~2-4)
將上述製備得到的有機膜形成用組成物(UDL-1~5、比較UDL-1~4)塗布於矽基板上,在大氣中350℃煅燒60秒後,測定膜厚,於其上分配PGMEA溶劑,放置30秒並旋乾,於100℃烘烤60秒,使PGMEA蒸發,測定膜厚並求出PGMEA處理前後之膜厚差。
如表3所示,本發明之有機膜形成用組成物(實施例2-1~2-5)經PGMEA處理後之殘膜率為99%以上,可知即使於大氣中,亦會發生交聯反應,並展現充分的溶劑耐性。反觀未添加交聯劑與熱酸產生劑的比較例2-3中,PGMEA處理後之殘膜率未達50%,未展現充分的溶劑耐性,為了展現充分的溶劑耐性需添加交聯劑及熱酸產生劑。由該結果可知,上述通式(1-1)中之(A-碳碳參鍵-Y)表示之次結構即使於大氣中亦會發生熱硬化反應,並展現溶劑耐性。
實施例3 填埋特性評價(實施例3-1~3-5、比較例3-1~3-4)
如圖3般,將上述有機膜形成用組成物(UDL-1~5、比較UDL-1~4)分別塗布在具有密集孔圖案(孔直徑0.16μm、孔深度0.50μm、相鄰兩個孔之中心間的距離0.32μm)之SiO2
晶圓基板上,使用加熱板於氧濃度管理為0.2%以下之氮氣流下在400℃煅燒60秒,形成有機膜8。所使用之基板係具有如圖3(G)(俯瞰圖)及(H)(剖面圖)所示之密集孔圖案的基底基板7(SiO2
晶圓基板)。使用掃描式電子顯微鏡(SEM)觀察獲得之各晶圓基板的剖面形狀,確認有機膜是否無孔隙(空隙)地填充在孔內部。結果示於表4。使用填埋特性差的有機膜形成用組成物時,本評價中,孔內部出現孔隙。使用填埋特性良好的有機膜形成用組成物時,本評價中,如圖3(I)所示,有機膜無孔隙地填充在孔內部。
由表4可知,本發明之有機膜形成用組成物(實施例3-1~3-5)可不產生孔隙地填充孔圖案,確認到具有良好的填埋特性。另一方面,比較例3-2~3-4中確認產生孔隙,填埋特性不良。由該結果可知,本發明之有機膜形成用組成物,藉由上述通式(1-1)中之(A-碳碳參鍵-Y)表示之結構而賦予流動性,使填埋特性得到改善。
實施例4 平坦化特性評價(實施例4-1~4-5、比較例4-1~4-4)
將有機膜形成用組成物(UDL-1~5、比較UDL-1~4)分別塗布在具有圖4所示之巨大孤立溝渠圖案(圖4(J)、溝渠寬度10μm、溝渠深度0.10μm)之基底基板9(SiO2
晶圓基板)上,於氧濃度管理為0.2%以下之氮氣流下,在400℃煅燒60秒。使用Park Systems公司製NX10原子力顯微鏡(AFM)觀察溝渠部分與非溝渠部分之有機膜10的高低差(圖4(K)中之delta10)。結果示於表5。本評價中,高低差越小,可以說平坦化特性越良好。此外,本評價中,使用通常膜厚約0.2μm之有機膜形成用組成物將深度0.10μm之溝渠圖案予以平坦化。為了評價平坦化特性之優劣而採用嚴格的條件。
由表5可知,本發明之有機膜形成用組成物(實施例4-1~4-5),相較於比較例4-1~4-4,溝渠部分與非溝渠部分之有機膜的高低差較小,確認到平坦化特性優異。比較例之有機膜形成用組成物中,添加有交聯劑者尤其為平坦差之結果。就平坦化特性而言,亦展現了上述通式(1-1)中之(A-碳碳參鍵-Y)表示之次結構的優越性。又,可知添加有高沸點溶劑之實施例4-4~4-5,相較於未添加高沸點溶劑之實施例4-1,由於高沸點溶劑之添加使得平坦性更為改善。
實施例5 耐熱特性評價(實施例5-1~5-5、比較例5-1~5-4)
將上述有機膜形成用組成物(UDL-1~5、比較UDL-1~4)分別塗布於矽基板上,在大氣中、180℃煅燒,形成115nm之塗布膜,測定膜厚。另外,將該基板在氧濃度管理為0.2%以下之氮氣流下,於400℃煅燒,測定膜厚(實施例5-1~5-5、比較例5-1~5-4)。該等結果示於表6。
由表6可知,本發明之有機膜形成用組成物(實施例5-1~5-5)即使於400℃煅燒後,膜厚減少仍未達1%,由本發明之有機膜形成用組成物形成之有機膜具有高耐熱性。反觀比較例5-2~5-4中,相較於本發明之有機膜形成用組成物,發生了大幅的膜厚減少。添加了交聯劑並硬化之比較例5-4中,亦發生了10%以上之膜厚減少。
實施例6 圖案形成試驗(實施例6-1~6-5、比較例6-1~6-4)
將上述有機膜形成用組成物(UDL-1~5、比較UDL-1~4)分別塗布於形成有300nm之SiO2
膜的矽晶圓基板上,在氧濃度管理為0.2%以下之氮氣流下,於400℃煅燒60秒,形成有機膜(光阻下層膜)。於其上形成CVD-SiON硬遮罩,進一步,塗布有機抗反射膜材料(ARC-29A:日產化學公司製),並在210℃烘烤60秒,形成膜厚80nm之有機抗反射膜,於其上塗布光阻上層膜材料之ArF用單層光阻,在105℃烘烤60秒,形成膜厚100nm之光阻膜。於光阻膜上塗布液潤保護膜材料(TC-1),在90℃烘烤60秒,形成膜厚50nm之保護膜。
光阻上層膜材料(ArF用單層光阻),係藉由使聚合物(RP1)、酸產生劑(PAG1)、鹼性化合物(Amine1),以表7之比例溶解於含有FC-4430(住友3M(股)製)0.1質量%之溶劑中,並利用0.1μm之氟樹脂製的過濾器進行過濾而製得。
液潤保護膜材料(TC-1),係藉由使保護膜聚合物(PP1)以表8之比例溶解於有機溶劑中,並利用0.1μm之氟樹脂製的過濾器進行過濾而製得。
然後,利用ArF液潤曝光裝置(Nikon(股)製;NSR-S610C、NA1.30、σ0.98/0.65、35度偶極s偏光照明、6%半階調相位偏移遮罩)進行曝光,於100℃烘烤(PEB)60秒,利用2.38質量%四甲基氫氧化銨(TMAH)水溶液顯影30秒,得到55nm 1:1之正型線與間距圖案。
然後,使用東京威力科創製蝕刻裝置Telius,以光阻圖案作為遮罩,利用乾蝕刻對有機抗反射膜與CVD-SiON硬遮罩進行蝕刻加工,形成硬遮罩圖案,以獲得之硬遮罩圖案作為遮罩,對有機膜進行蝕刻而形成有機膜圖案,並以獲得之有機膜圖案作為遮罩,進行SiO2
膜的蝕刻加工。蝕刻條件如下所示。
光阻圖案向SiON硬遮罩轉印的條件。
腔室壓力10.0Pa
RF功率1,500W
CF4
氣體流量75sccm
O2
氣體流量15sccm
時間15sec
硬遮罩圖案向有機膜轉印的條件。
腔室壓力2.0Pa
RF功率500W
Ar氣體流量75sccm
O2
氣體流量45sccm
時間120sec
有機膜圖案向SiO2
膜轉印的條件。
腔室壓力2.0Pa
RF功率2,200W
C5
F12
氣體流量20sccm
C2
F6
氣體流量10sccm
Ar氣體流量300sccm
O2
60sccm
時間90sec
利用日立製作所(股)製電子顯微鏡(S-4700)觀察圖案剖面的結果示於表9。
如表9所示,由本發明之有機膜形成用組成物(實施例6-1~6-5)之結果,確認到光阻上層膜圖案皆最終良好地轉印至基板,本發明之有機膜形成用組成物適合使用在利用多層光阻法所為之微細加工。另一方面,比較例6-2~6-3,於氮氣環境下的耐熱性不足,且如比較例1-2~1-3所示未充分硬化,因而圖案加工時發生圖案崩塌,無法獲得良好的圖案。比較例6-4中,耐熱性不足但可形成圖案。
實施例7 圖案形成試驗(實施例7-1~7-5、比較例7-1~7-4)
將上述有機膜形成用組成物(UDL-1~5、比較UDL-1~4)分別塗布於具有溝渠圖案(溝渠寬度10μm、溝渠深度0.10μm)的SiO2
晶圓基板上,於氧濃度管理為0.2%以下之氮氣流下,在400℃煅燒60秒,除此以外,以與實施例6相同的方法形成疊層膜,並進行圖案化、乾蝕刻,觀察得到的圖案形狀。
【表10】
如表10所示,由本發明之有機膜形成用組成物(實施例7-1~7-5)之結果,確認到光阻上層膜圖案皆最終良好地轉印至基板,本發明之有機膜形成用組成物適合使用在利用多層光阻法所為之微細加工。另一方面,比較例7-2~7-3中,於氮氣環境下的耐熱性不足,且如比較例1-2~1-3所示未充分硬化,又,圖案的填埋不良,因而圖案加工時發生圖案崩塌,無法獲得良好的圖案。比較例7-4中,雖然獲得溶劑耐性而成為硬化膜,但圖案的填埋不良,因而圖案加工時發生圖案崩塌,最終未能獲得良好的圖案。
由上可知,若為含有本發明之通式(1-1)表示之化合物的本發明之有機膜形成用組成物,則具有良好的乾蝕刻耐性,且即使在不含氧的鈍性氣體下,仍兼具400℃以上之耐熱性及高程度填埋/平坦化特性,故作為使用於多層光阻法之有機膜形成用組成物係極為有用,又,若為使用了本發明之有機膜形成用組成物的圖案形成方法,即使被加工基板為具有圖案的基板,亦能以高精度形成微細的圖案。
此外,本發明並不限定於上述實施形態。上述實施形態係例示,和本發明之申請專利範圍記載之技術思想有實質上相同的構成且可發揮同樣的作用效果者皆包括在本發明之技術範圍內。
1‧‧‧基板
2‧‧‧被加工層
2a‧‧‧形成於被加工層之圖案
3‧‧‧有機膜
3’‧‧‧有機膜形成用組成物
3a‧‧‧有機膜圖案
4‧‧‧含矽光阻中間膜
4a‧‧‧含矽光阻中間膜圖案
5‧‧‧光阻上層膜
5a‧‧‧光阻上層膜圖案
6‧‧‧曝光部分
7‧‧‧具有密集孔圖案之基底基板
8‧‧‧有機膜
9‧‧‧具有巨大孤立溝渠圖案之基底基板
10‧‧‧有機膜
delta10‧‧‧溝渠部分與非溝渠部分的有機膜之膜厚的差
[圖1]係本發明中之平坦化特性的說明圖。
[圖2](A)~(F)係利用3層光阻法之圖案形成方法之一例的說明圖。
[圖3](G)~(I)係實施例中之填埋特性評價方法的說明圖。
[圖4](J)~(K)係實施例中之平坦化特性評價方法的說明圖。
1‧‧‧基板
3‧‧‧有機膜
3’‧‧‧有機膜形成用組成物
Claims (9)
- 一種有機膜形成用組成物,含有(A)下列通式(1-1)表示之化合物、及(B)有機溶劑;
- 如申請專利範圍第4至6項中任一項之有機膜形成用組成物,更含有(C)酸產生劑、(D)界面活性劑、(E)交聯劑、及(F)塑化劑中之1種以上。
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