KR101988997B1 - Polymer, organic layer composition, and method of forming patterns - Google Patents
Polymer, organic layer composition, and method of forming patterns Download PDFInfo
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- KR101988997B1 KR101988997B1 KR1020160142173A KR20160142173A KR101988997B1 KR 101988997 B1 KR101988997 B1 KR 101988997B1 KR 1020160142173 A KR1020160142173 A KR 1020160142173A KR 20160142173 A KR20160142173 A KR 20160142173A KR 101988997 B1 KR101988997 B1 KR 101988997B1
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- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 229920000642 polymer Polymers 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000012044 organic layer Substances 0.000 title description 2
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 239000000126 substance Substances 0.000 claims abstract description 21
- 239000010408 film Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 239000010409 thin film Substances 0.000 claims description 29
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229920002120 photoresistant polymer Polymers 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 15
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- 239000010703 silicon Substances 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000002560 nitrile group Chemical group 0.000 claims description 12
- 229910005965 SO 2 Inorganic materials 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 238000005530 etching Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052714 tellurium Inorganic materials 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 230000003667 anti-reflective effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000000243 solution Substances 0.000 description 45
- 239000010410 layer Substances 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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- 238000003756 stirring Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 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 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 230000021736 acetylation Effects 0.000 description 7
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
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- 239000007787 solid Substances 0.000 description 7
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- 230000007797 corrosion Effects 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- -1 acetylene compound Chemical class 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- 229940008406 diethyl sulfate Drugs 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- ICPUEJATIRSQEG-UHFFFAOYSA-N 2-bromonaphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=C(Br)C=CC2=C1 ICPUEJATIRSQEG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
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- 239000002184 metal Substances 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BPJINPBZQICULW-UHFFFAOYSA-N 1,3-bis(methoxymethyl)benzene Chemical compound COCC1=CC=CC(COC)=C1 BPJINPBZQICULW-UHFFFAOYSA-N 0.000 description 1
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- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
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- 125000003710 aryl alkyl group Chemical group 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 230000003746 surface roughness Effects 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 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
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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
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0334—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane
- H01L21/0337—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane characterised by the process involved to create the mask, e.g. lift-off masks, sidewalls, or to modify the mask, e.g. pre-treatment, post-treatment
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/324—Thermal treatment for modifying the properties of semiconductor bodies, e.g. annealing, sintering
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Abstract
A polymer containing a structural unit represented by the formula (1), a monomer represented by the formula (3), an organic film composition comprising a solvent, and a pattern forming method using the organic film composition.
[Chemical Formula 1]
(3)
The definition of A, B, A 0 , A 1 , A 2 , L 1 , L 2 , L 3 , L 4 , X 1 , X 2 , X 3 , X 4 , Lt; / RTI >
Description
An organic film composition, and a method of forming a pattern using the organic film composition.
Recently, highly integrated design due to the miniaturation and complexity of electronic devices has accelerated the development of more advanced materials and related processes, and therefore lithography using existing photoresists also requires new patterning materials and techniques .
In the patterning process, an organic film called a hardmask layer, which is a hard interlayer, can be formed in order to transfer a fine pattern of photoresist to a substrate to a sufficient depth without collapse.
The hard mask layer acts as an interlayer to transfer the fine pattern of the photoresist to the material layer through the selective etching process. Therefore, the hard mask layer needs properties such as heat resistance and corrosion resistance to withstand the multiple etching process.
Meanwhile, it has recently been proposed that the hard mask layer is formed by a spin-on coating method instead of the chemical vapor deposition method. The spin-on coating method is not only easy to process but also can improve gap-fill and planarization properties.
Generally, heat resistance and corrosion resistance are required to be compatible with spin-on characteristics, and an organic film material that can satisfy all of these properties.
One embodiment provides an organic film composition that is capable of being coated in a spin-on manner while exhibiting excellent corrosion resistance.
Another embodiment provides a method of forming a pattern using the organic film composition.
According to one embodiment, there is provided an organic film composition comprising a polymer comprising a structural unit represented by the following formula (1), a monomer represented by the following formula (3), and a solvent.
[Chemical Formula 1]
In Formula 1,
A is a substituted or unsubstituted aromatic ring-containing group, a substituted or unsubstituted heteroaromatic ring-containing group, or a combination thereof,
B is a divalent organic group,
Wherein at least one of A and B is substituted by a functional group comprising a moiety represented by the following formula:
(2)
In Formula 2,
Z is hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
* Is the connection point:
(3)
In Formula 3,
A 0 , A 1 and A 2 each independently represent a substituted or unsubstituted aromatic ring-containing group, and one or two or more of A 0 , A 1 and A 2 may have a substituted or unsubstituted amino group, Or an unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, or a nitrile group,
L 1 , L 2 , L 3 and L 4 are each independently a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C30 arylene group,
X 1 , X 2 , X 3 and X 4 are each independently hydrogen, a hydroxy group, a substituted or unsubstituted amino group, a halogen atom, or a combination thereof, X 1 and X 2 can not be hydrogen at the same time, X 3 and X 4 can not simultaneously be hydrogen,
m and n are each independently an integer of 0 to 2, the sum of m and n is 1 or more,
Provided that when m is 0, at least one of A 0 and A 2 is a substituted or unsubstituted amino group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, And when n is 0, at least one of A 0 and A 1 is an amino group substituted or unsubstituted in the structure thereof, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide Group, or a nitrile group.
The functional group having a moiety represented by Formula 2 may be represented by Formula 2 below.
[Formula 2 ']
In the above formula (2 '),
W is O, S, NR a or CR b R c , wherein R a to R c are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-
Z is hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
a is 0 or 1,
b is an integer of 0 to 10,
* Is the connection point.
In Formula 3, A 0 , A 1, and A 2 each independently may contain a substituted or unsubstituted moiety selected from the following Group 1.
[Group 1]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.
In Formula 3, at least one of A 0 , A 1 and A 2 may be a polycyclic ring group.
In Formula 3, at least one of A 0 , A 1 and A 2 may include at least one functional group represented by the following Formula 4 in its structure.
[Chemical Formula 4]
In Formula 4,
W is O, S, NR a or CR b R c , wherein R a to R c are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-
Y is a substituted or unsubstituted amino group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, a nitrile group, or a combination thereof,
a is 0 or 1,
b is an integer of 0 to 10,
* Is the connection point.
When the monomer includes a substituted or unsubstituted acetylene group, it may be represented by any of the following formulas (3a) to (3d).
[Chemical Formula 3]
[Formula 3b]
[Chemical Formula 3c]
(3d)
In the above formulas (3a) to (3d)
A 3 , A 4 and A 5 are each independently a substituted or unsubstituted aromatic ring-containing group,
W is O, S, NR a or CR b R c , wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.
In Formula 1, A may be a substituted or unsubstituted moiety selected from the following Groups 1 and 2.
[Group 1]
[Group 2]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group or a combination thereof.
In the group 2,
Z 1 and Z 2 are each independently NR d , O, S, Te or Se,
Z 3 to Z 5 are N,
R d and R e are each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen atom, a halogen-containing group, a substituted or unsubstituted 1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, It is a combination.
The above B may be represented by any one of the following formulas (Z1) to (Z4).
(Z1)
(Z2)
(Z3)
(Z4)
In the above general formulas Z1 to Z4,
e and f are each independently 0 or 1,
g is an integer of 1 to 5,
Y 1 to Y 4 are each independently any one of a substituted or unsubstituted moiety selected from the following Group 3,
* Is the connection point:
[Group 3]
In the group 3,
M, M 'and M "are each independently a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2, CR f R g, NR h, or carbonyl, wherein R f to R h are each Independently, hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof,
L 1 is a substituted or unsubstituted C6 to C50 arylene group, a substituted or unsubstituted C1 to C10 alkylene oxide-containing group, or a combination thereof,
r is an integer from 0 to 10,
s is an integer of 0 to 10,
k is an integer of 0 to 3;
The polymer may further include a structural unit represented by the following general formula (5).
[Chemical Formula 5]
In Formula 5,
X 0 is a substituted or unsubstituted aromatic ring-containing group, a substituted or unsubstituted heteroaromatic ring-containing group, or a combination thereof,
L 0 is a divalent organic group,
* Is the connection point.
In Formula 5, X 0 may be a substituted or unsubstituted moiety selected from Groups 1 and 2 below.
[Group 1]
[Group 2]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group or a combination thereof,
In the group 2,
Z 1 and Z 2 are each independently NR d , O, S, Te or Se,
Z 3 to Z 5 are N,
R d and R e are each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen atom, a halogen-containing group, a substituted or unsubstituted 1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, It is a combination.
The polymer may contain at least one oxygen atom in its structural unit.
The monomer may have a molecular weight of 500 to 50,000.
The polymer may have a weight average molecular weight of 500 to 200,000.
The weight ratio of the polymer and the monomer may be 70:30 to 30:70.
According to another embodiment, there is provided a method of manufacturing a semiconductor device comprising the steps of providing a material layer on a substrate, applying the above-described organic film composition on the material layer, heat treating the organic film composition to form a hard mask layer, Containing thin film layer; forming a photoresist layer on the silicon-containing thin film layer; exposing and developing the photoresist layer to form a photoresist pattern; Selectively removing the hard mask layer and exposing a portion of the material layer, and etching the exposed portion of the material layer.
The step of applying the organic film composition may be performed by a spin-on coating method.
The heat treatment may include a first heat treatment performed at 50 to 250 ° C, and a second heat treatment followed by the first heat treatment and proceeding at 200 to 500 ° C.
And forming a bottom anti-reflective layer (BARC) before the step of forming the photoresist layer.
Provided is an organic film composition which can be coated by a spin-on method and has excellent corrosion resistance by containing a predetermined polymer and a predetermined additive. The organic film prepared from the organic film composition has excellent film density and film flatness.
Fig. 1 is a view for explaining a method for evaluating the planarization characteristic (step characteristic)
2 is a view for explaining a method of evaluating the thickness uniformity characteristic.
Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
Unless otherwise defined herein, "substituted" means that the hydrogen atom in the compound is a halogen atom (F, Br, Cl, or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, A thio group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, A C3 to C30 heteroaryl group, a C3 to C30 heteroaryl group, a C3 to C30 cycloalkyl group, a C3 to C30 aryl group, a C7 to C30 arylalkyl group, a C1 to C30 alkoxy group, a C1 to C20 heteroalkyl group, a C2 to C20 hetero aryl group, Substituted with a substituent selected from the group consisting of a cycloalkenyl group, a C 6 to C 15 cycloalkynyl group, a C 2 to C 30 heterocycloalkyl group, and combinations thereof.
In addition, unless otherwise defined herein, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S and P.
An organic film composition according to one embodiment will be described below.
The organic film composition according to an embodiment provides an organic film composition comprising a polymer containing a structural unit represented by the following formula (1), a monomer represented by the following formula (3), and a solvent.
[Chemical Formula 1]
In Formula 1,
A is a substituted or unsubstituted aromatic ring-containing group, a substituted or unsubstituted heteroaromatic ring-containing group, or a combination thereof,
B is a divalent organic group,
Wherein at least one of A and B is substituted by a functional group comprising a moiety represented by the following formula:
(2)
In Formula 2,
Z is hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
* Is the connection point:
(3)
In Formula 3,
A 0 , A 1 and A 2 each independently represent a substituted or unsubstituted aromatic ring-containing group, and one or two or more of A 0 , A 1 and A 2 may have a substituted or unsubstituted amino group, Or an unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, or a nitrile group,
L 1 , L 2 , L 3 and L 4 are each independently a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C30 arylene group,
X 1 , X 2 , X 3 and X 4 are each independently hydrogen, a hydroxy group, a substituted or unsubstituted amino group, a halogen atom, or a combination thereof, X 1 and X 2 can not be hydrogen at the same time, X 3 and X 4 can not simultaneously be hydrogen,
m and n are each independently an integer of 0 to 2, the sum of m and n is 1 or more,
Provided that when m is 0, at least one of A 0 and A 2 is a substituted or unsubstituted amino group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, When n is 0, at least one of A 0 and A 1 is a substituted or unsubstituted amino group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, Containing nitrile group.
In the present specification, the term "acetylene group" means a monovalent functional group formed by substituting one hydrogen atom in an acetylene compound, and the term "azide group" means a monovalent functional group formed by substituting one hydrogen atom in an azide compound.
The organic film composition includes a polymer having a predetermined structure and a monomer having a predetermined structure. First, the polymer will be described.
The polymer includes one or more structural units represented by the formula (1), and includes an aromatic ring group-containing moiety represented by A and a linking moiety represented by B in the structural unit.
For example, A may be a substituted or unsubstituted aromatic ring-containing group, and may include, but is not limited to, a substituted or unsubstituted moiety selected, for example, from the following group 1.
[Group 1]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.
As another example, A may be a substituted or unsubstituted heteroaromatic ring-containing group, including, but not limited to, a substituted or unsubstituted moiety selected from the following group 2.
[Group 2]
In the group 2,
Z 1 and Z 2 are each independently NR d , O, S, Te or Se,
Z 3 to Z 5 are N,
R d and R e are each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen atom, a halogen-containing group, a substituted or unsubstituted 1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, It is a combination.
As another example, A may be a combination of a substituted or unsubstituted aromatic ring-containing group and a substituted or unsubstituted heteroaromatic ring-containing group. For example, in Formula 1, A may be a substituted or unsubstituted aromatic ring- An unsubstituted benzene ring, and may include, for example, 2 to 6 substituted or unsubstituted benzene rings. Wherein the benzene ring may be substituted by at least one hydroxy group.
In formula (1), B representing a linking group may be a divalent organic linear group, a divalent organic ring group, or a combination thereof. For example, B may be represented by any one of the following formulas (Z1) to (Z4), but is not limited thereto.
(Z1)
(Z2)
(Z3)
(Z4)
In the above general formulas Z1 to Z4,
e and f are each independently 0 or 1,
g is an integer of 1 to 5,
Y 1 to Y 4 are each independently any one of a substituted or unsubstituted moiety selected from the following Group 3,
* Is the connection point:
[Group 3]
In the group 3,
M, M 'and M "are each independently a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2, CR f R g, NR h, or carbonyl, wherein R f to R h are each Independently, hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof,
L 1 is a substituted or unsubstituted C6 to C50 arylene group, a substituted or unsubstituted C1 to C10 alkylene oxide-containing group, or a combination thereof,
r is an integer from 0 to 10,
s is an integer from 3 to 10,
k is an integer of 1 to 3;
In Formula 1, at least one of A and B is substituted by an acetylene-containing group represented by Formula 2 above. For example, the aromatic ring-containing group or the heteroaromatic ring-containing group represented by A is substituted by an acetylene-containing group, the connecting group represented by B is substituted by an acetylene-containing group, or both the A and B moieties are acetylene- Lt; / RTI > group. In this case, the number of substituents is not particularly limited.
For example, the functional group having a moiety represented by the formula (2) may be a group represented by the following formula (2 '), but is not limited thereto.
[Formula 2 ']
In the above formula (2 '),
W is O, S, NR a or CR b R c , wherein R a to R c are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-
Z is hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
a is 0 or 1,
b is an integer of 0 to 10,
* Is the connection point.
For example, the functional group containing a moiety represented by the formula (2) may be a group represented by the following formula (2), but is not limited thereto.
[Chemical Formula 2] "
In the above formula (2)
W is O, S, NR a or CR b R c , wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a halogen atom, a halogen-containing group,
a is 0 or 1,
* Is the connection point.
For example, the polymer may comprise at least one oxygen atom in its structure.
The polymer has an aromatic ring-containing group represented by A or a heteroaromatic ring-containing group represented by A in the structural unit, thereby securing corrosion-resistance, and flexibility can be ensured by including an organic group represented by B have. Further, by introducing at least one acetylene into the A or B, the acetylene forms a ring structure when the polymer is cured, so that corrosion resistance of the polymer can be further improved. Accordingly, the organic film formed using the polymer has excellent film density. In addition, the organic film formed by using the polymer can ensure thickness uniformity.
The polymer may further include a structural unit represented by the following general formula (5).
[Chemical Formula 5]
In Formula 5,
X 0 is a substituted or unsubstituted aromatic ring-containing group, a substituted or unsubstituted heteroaromatic ring-containing group, or a combination thereof,
L 0 is a divalent organic group,
* Is the connection point.
In Formula 5, X may be a substituted or unsubstituted moiety selected from the group 1 and 2, and L 0 is a linking group as described for B in Formula 1 above. However, the structural unit represented by the formula (8) does not necessarily include an acetylene functional group, unlike the structural unit represented by the formula (1).
Hereinafter, the monomers contained in the organic film composition will be described.
The monomer is represented by the following formula (3) as described above.
(3)
In Formula 3,
A 0 , A 1 and A 2 each independently represent a substituted or unsubstituted aromatic ring-containing group, and one or two or more of A 0 , A 1 and A 2 may have a substituted or unsubstituted amino group, Or an unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, or a nitrile group,
L 1 , L 2 , L 3 and L 4 are each independently a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C30 arylene group,
X 1 , X 2 , X 3 and X 4 are each independently hydrogen, a hydroxy group, a substituted or unsubstituted amino group, a halogen atom, or a combination thereof, X 1 and X 2 can not be hydrogen at the same time, X 3 and X 4 can not simultaneously be hydrogen,
m and n are each independently an integer of 0 to 2, the sum of m and n is 1 or more,
Provided that when m is 0, at least one of A 0 and A 2 contains a substituted or unsubstituted amine group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, or a nitrile group , and when n is 0, at least one of A 0 and A 1 is a substituted or unsubstituted amino group, a substituted or unsubstituted vinyl group substituted or unsubstituted acetylene group, an azide group, or a nitrile group in its structure do.
For example, in Formula 3, one or two or more of A 0 , A 1, and A 2 may contain a functional group represented by the following Formula 4 in its structure.
[Chemical Formula 4]
In Formula 4,
W is O, S, NR a or CR b R c , wherein R a to R c are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-
Y is a substituted or unsubstituted amino group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, a nitrile group, or a combination thereof,
a is 0 or 1,
b is an integer of 0 to 10,
* Is the connection point.
The functional group represented by Formula 4 is a substituted or unsubstituted amine group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, or a nitrile group.
The monomer may contain, for example, one or two or more functional groups represented by the formula (4) in its structure.
For example, in the formula (3) representing the monomer, A 0 , A 1 and A 2 each independently may contain a substituted or unsubstituted moiety selected from Group 1 described above, but are not limited thereto.
For example, in formula (3) representing the monomer, at least one of A 0 , A 1 and A 2 may be a polycyclic ring group.
For example, the monomer may be represented by any one of the following formulas (3a) to (3d), but is not limited thereto.
[Chemical Formula 3]
[Formula 3b]
[Chemical Formula 3c]
(3d)
In the above formulas (3a) to (3d)
A 3 , A 4 and A 5 are each independently a substituted or unsubstituted aromatic ring-containing group,
W is O, S, NR a or CR b R c , wherein each of R a to R c is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.
As described above, the organic film composition is a polymer in which acetylene is introduced, and an aromatic ring-containing compound is a substituted or unsubstituted amine group, a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, an azide group, And a monomer having at least one nitrile group.
When an organic film composition is prepared by using the polymer and the monomer simultaneously, the acetylene functional group introduced into the polymer reacts with amine, acetylene, azide, etc. introduced into the monomer at the time of curing to form a ring, Is relatively increased. As a result, corrosion resistance is improved and the etch selectivity can be improved. Therefore, the organic film formed using the organic film composition is excellent in film density and pattern forming property.
For example, the polymer may have a weight average molecular weight of about 500 to 200,000. By having a weight average molecular weight in the above range, it is possible to optimize by controlling the carbon content of the organic film composition (for example, hard mask composition) containing the polymer and the solubility in solvents. Also for example, the monomer may have a molecular weight of about 500 to 50,000.
The solvent contained in the organic film composition is not particularly limited as long as it has sufficient solubility or dispersibility in the polymer. Examples of the solvent include propylene glycol, propylene glycol diacetate, methoxypropanediol, diethylene glycol, diethylene glycol butyl ether, (Ethylene glycol) monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, ethyl lactate, gamma-butyrolactone, N, N-dimethylformamide, N, Amide, methyl pyrrolidone, methyl pyrrolidinone, acetylacetone, and ethyl 3-ethoxypropionate.
The polymer may be included in an amount of about 0.1 to 50% by weight based on the total amount of the organic film composition. By including the polymer in the above range, the thickness, surface roughness, and leveling of the organic film can be controlled.
The monomer may be contained in an amount of about 0.1 to 50% by weight based on the total amount of the organic film composition, for example, about 5 to 50% by weight based on the total amount of the organic film composition.
For example, the weight ratio of the polymer and the monomer may be adjusted within a range of 70:30 to 30:70, but is not limited thereto.
The organic film composition may further include additives such as a surfactant, a crosslinking agent, a thermal acid generator, and a plasticizer.
The surfactant may be, for example, an alkylbenzenesulfonate, an alkylpyridinium salt, a polyethylene glycol, or a quaternary ammonium salt, but is not limited thereto.
Examples of the cross-linking agent include melamine-based, substitution-based, or polymer-based ones. Preferably, the crosslinking agent having at least two crosslinking substituents is, for example, a methoxymethylated glycerol, a butoxymethylated glyceryl, a methoxymethylated melamine, a butoxymethylated melamine, a methoxymethylated benzoguanamine, a butoxy Methylated benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or butoxymethylated thiourea can be used.
As the crosslinking agent, a crosslinking agent having high heat resistance can be used. As the crosslinking agent having a high heat resistance, a compound containing a crosslinking forming substituent group having an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule can be used.
The acid generator may be an acidic compound such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid or naphthalenecarboxylic acid and / , 4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters, but are not limited thereto.
The additive may be included in an amount of about 0.001 to 40 parts by weight based on 100 parts by weight of the organic film composition. By including it in the above range, the solubility can be improved without changing the optical properties of the organic film composition.
According to another embodiment, there is provided an organic film produced using the organic film composition described above. The organic layer may be in the form of a hardened layer, for example, a hard mask layer, a planarization layer, a sacrificial layer, a filler, etc., and an organic thin film used for electronic devices, .
Hereinafter, a method of forming a pattern using the organic film composition described above will be described.
The method of forming a pattern according to one embodiment includes the steps of providing a material layer on a substrate, applying an organic film composition comprising the polymer and the solvent on the material layer, heat treating the organic film composition to form a hard mask layer Containing thin film layer on the hard mask layer; forming a photoresist layer on the silicon-containing thin film layer; exposing and developing the photoresist layer to form a photoresist pattern; Selectively removing the silicon-containing thin film layer and the hard mask layer using a mask to expose a portion of the material layer, and etching the exposed portion of the material layer.
The substrate may be, for example, a silicon wafer, a glass substrate, or a polymer substrate.
The material layer is a material to be finally patterned and may be a metal layer such as aluminum, copper, or the like, a semiconductor layer such as silicon, or an insulating layer such as silicon oxide, silicon nitride, or the like. The material layer may be formed by, for example, a chemical vapor deposition method.
The organic film composition is as described above, and may be prepared in a solution form and applied by a spin-on coating method. At this time, the coating thickness of the organic film composition is not particularly limited, but may be applied to a thickness of about 50 to 10,000 ANGSTROM.
The heat treatment of the organic film composition may be performed at about 100 to 500 DEG C for about 10 seconds to 1 hour.
For example, the heat treatment may include a first heat treatment performed at 50 to 250 ° C, and a second heat treatment subsequent to the first heat treatment and proceeding at 200 to 500 ° C.
The silicon-containing thin film layer may be formed of a material such as SiCN, SiOC, SiON, SiOCN, SiC and / or SiN.
Further, a bottom anti-reflective coating (BARC) may be further formed on the silicon-containing thin film layer before the step of forming the photoresist layer.
The step of exposing the photoresist layer may be performed using, for example, ArF, KrF or EUV. Further, after the exposure, the heat treatment process may be performed at about 100 to 500 ° C.
The step of etching the exposed portion of the material layer may be performed by dry etching using an etching gas, and the etching gas may be, for example, CHF 3 , CF 4 , Cl 2 , BCl 3 and a mixed gas thereof.
The etched material layer may be formed in a plurality of patterns, and the plurality of patterns may be a metal pattern, a semiconductor pattern, an insulation pattern, or the like, and may be applied to various patterns in a semiconductor integrated circuit device, for example.
Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.
Polymer synthesis
Polymerization Example One
Resin polymerization
The flask was charged with naphthalen-1-ol (14.2 g), paraformaldehyde (6 g), p-toluenesulfonic acid hydrate (1.9 g) and propylene glycol monomethyl ether acetate (PGMEA) (33 g) And the polymerization reaction was carried out. During the reaction, the molecular weight was confirmed by GPC, and the reaction was completed when the weight average molecular weight was 2,000 to 3,500. After completion of the polymerization reaction, the reaction product was slowly cooled to room temperature, and 100 g of hexane was added thereto to extract propylene glycol monomethyl ether acetate. Then, the reaction product was removed using distilled water and methanol to obtain a polymer containing the structural unit represented by the following formula (Weight average molecular weight (Mw) = 3,000).
[Chemical Formula 1a ']
Acetylation ( Acetylation ) reaction
The polymer (10 g) containing the structural unit of formula (1a ') is dissolved in DMF (40 mL) and stirred in ice water. After 10 minutes of stirring, NaH (1 g) is slowly added dropwise, and the mixture is stirred in ice water for 30 minutes, and then propyl bromide (80% in tolutene) (5.5 g) is added dropwise. Once the reaction is complete, dilute the reaction mixture with EtOAc (100 mL) and rinse with water several times to remove DMF. When the DMF was completely removed, the remaining EtOAc was removed to obtain the compound of formula (Ia).
[Formula 1a]
Polymerization Example 2
Resin polymerization
4,4'- (9H-fluorene-9,9-diyl) diphenol (14 g), 1,4-bis Propyleneglycol monomethyl ether acetate (PGMEA) (20 g) and diethylsulfate (0.25 g) were added at 100 占 폚 to the synthesis example 1, a polymer containing a structural unit represented by the formula (1b ') was obtained. (Weight average molecular weight (Mw) = 3,700).
[Formula 1b ']
Acetylation ( Acetylation _) reaction
The same procedure as in Synthesis Example 1 was carried out using 9 g of the polymer containing the structural unit of formula 1b ', DMF (45 mL), NaH (0.9 g) and propyl bromide (80% in tolutene) To give the compound of formula (Ib).
[Chemical Formula 1b]
Polymerization Example 3
Resin polymerization
(18 g), 1,3-bis (methoxymethyl) benzene (6.6 < RTI ID = 0.0 & (1 g), propylene glycol monomethyl ether acetate (PGMEA) (25 g) and diethylsulfate (0.2 g) were reacted at 110 ° C in the same manner as in the resin polymerization of Synthesis Example 1, Units were obtained. (Weight average molecular weight (Mw) = 3,800).
[Chemical Formula 1c ']
Acetylation ( Acetylation _) reaction
(10 g), a DMF (45 mL), NaH (0.7 g) and propargyl bromide (80% in tolutene) (2.5 g) containing the structural unit of the formula 1c ' Acetylation to obtain the compound of formula (1c).
[Chemical Formula 1c]
compare Polymerization Example One
(64 g) and diethylsulfate (0.3 g) were added to the reaction mixture at a temperature of 100 占 폚 (Polymer 1d) containing the structural unit represented by the formula (1d) was obtained by the same method as the resin polymerization of the synthesis example 1. (Weight average molecular weight (Mw) = 3,000).
≪ RTI ID = 0.0 &
Monomer synthesis
Synthetic example One
30 g (0.1 mol) of chororene, 27 g (0.1 mol) of bromonaphthoyl chloride, and 150 g of 1,2-dichloroethane were placed in a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube. After 15 minutes, 14.67 g (0.11 mol) of trichloroaluminum was slowly added and the reaction was carried out at room temperature for 1 hour. After confirming that all of the coronene was removed, the reaction product was added to methanol, and then the precipitate was filtered to remove trichloroaluminum. The powder obtained through the filtration was placed in a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube, and 44 g (0.45 mol) of 1-dodecan sulfate, 15 g (0.54 mol) of potassium hydroxide and N, N- 262 g of amide was added thereto, followed by stirring at 100 DEG C for 5 hours. After completion of the reaction, the reaction product was cooled, the pH was adjusted to pH <5 with 7% hydrogen chloride solution, and the resulting precipitate was filtered. Thereafter, the obtained filtrate was dried in a vacuum oven to remove moisture.
To the powder thus obtained, 160 g of THF was added again to prepare a solution. An aqueous solution of 8 g (0.21 mol) of sodium borohydride was slowly added to the solution, followed by stirring at room temperature for 12 hours. The pH of the reaction solution is adjusted to pH <5 with 7% hydrogen chloride solution, extracted with ethyl acetate, and the organic solvent is reduced in pressure.
0.6 g (0.0008 mol) of bis (triphenylphosphine) palladium (II) dichloride, Pd (PPh3) 2Cl2), 10 g (0.02 mol) of the synthesized polymer, (0.0008 mol) of copperiodide, 0.44 g (0.0016 mol) of triphenylphosphine, and 36 mL of triethylamine were dissolved in 60 mL of tetrahydrofuran. 3.5 g of ethynyltrimethylsilane was added thereto, followed by stirring at 80 ° C for 3 hours. After completion of the reaction, the reaction product was purified by filtration using silica gel. 12.5 g (1 equivalent) of the purified solid was dissolved in 250 mL of a MeOH / THF (volume ratio = 1/2) solution, to which 20 g of potassium carbonate (7 equivalents) was added and stirred at room temperature for 6 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and reduced in pressure to obtain the compound represented by Formula 3-1.
[Formula 3-1]
Synthetic example 2
10 g (0.05 mol) of pyrene, 27 g (0.1 mol) of bromonaphthoyl chloride and 150 g of 1,2-dichloroethane are added to a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube. After 15 minutes, 14.67 g (0.11 mol) of trichloroaluminum was slowly added and the reaction was carried out at room temperature for 1 hour. After confirming that the pyrene was completely removed, the reaction product was added to methanol, and the precipitate was filtered to remove trichloroaluminum. The powder obtained through the above filtration was placed in a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube, and 44 g (0.22 mol) of 1-dodecan sulfate, 15 g (0.25 mol) of potassium hydroxide and N, N- 262 g of amide was added thereto, followed by stirring at 100 DEG C for 5 hours. After completion of the reaction, the reaction product was cooled, the pH was adjusted to pH <5 with 7% hydrogen chloride solution, and the resulting precipitate was filtered. Thereafter, the obtained filtrate was dried in a vacuum oven to remove moisture.
To the powder thus obtained, 160 g of THF was added again to prepare a solution. An aqueous solution of 8 g (0.21 mol) of sodium borohydride was slowly added to the solution, followed by stirring at room temperature for 12 hours. The pH of the reaction solution is adjusted to pH <5 with 7% hydrogen chloride solution, extracted with ethyl acetate, and the organic solvent is reduced in pressure.
0.6 g (0.0008 mol) of bis (triphenylphosphine) palladium (II) dichloride, Pd (PPh 3) 2 Cl 2), 10 g of copper iodide (0.0008 mol) of copperiodide, 0.44 g (0.0016 mol) of triphenylphosphine, and 36 mL of triethylamine were dissolved in 60 mL of tetrahydrofuran. 3.5 g of ethynyltrimethylsilane was added thereto, followed by stirring at 80 ° C for 3 hours. After completion of the reaction, the reaction product was purified by filtration using silica gel. 12.5 g (1 equivalent) of the purified solid was dissolved in 250 mL of a MeOH / THF (volume ratio = 1/2) solution, to which 20 g of potassium carbonate (7 equivalents) was added and stirred at room temperature for 6 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and reduced in pressure to obtain a compound represented by the formula (3-2).
[Formula 3-2]
Synthetic example 3
10 g (0.05 mol) of pyrene, 8.43 g (0.05 mol) of 4-methoxybenzoyl chloride and 100.11 g of 1,2-dichloroethane were added to a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube to prepare a solution . Subsequently, 6.59 g (0.0494 mol) of aluminum chloride was slowly added to the solution, followed by stirring at room temperature for 2 hours. When the reaction was completed, methanol was added to the solution, and the resulting precipitate was filtered and dried.
Then, 15.46 g (0.0460 mol) of the compound obtained above, 4.07 g (0.0153 mol) of 1,3,5-benzenetricarboxylic acid chloride and 102.62 g of 1,2-dichloroethane were added to the flask to prepare a solution. Subsequently, 6.13 g (0.0460 mol) of aluminum chloride was slowly added to the solution, followed by stirring at room temperature for 6 hours. When the reaction was completed, methanol was added to the solution, and the resulting precipitate was filtered and dried.
15.17 g (0.0130 mol) of the compound obtained above, 13.18 g (0.0651 mol) of 1-dodecan sulfate, 4.38 g (0.0781 mol) of potassium hydroxide and 76.37 g of N, N-dimethylformamide were added to the flask, And stirred for 3 hours. The mixture was then cooled, neutralized to about pH 6-7 with 5% hydrogen chloride solution, and the precipitate formed was filtered and dried.
11.84 g (0.0105 mol) of the compound obtained above and 40 g of tetrahydrofuran were added to the flask to prepare a solution. Then, an aqueous solution of 7.98 g (0.2108 mol) of sodium borohydride was slowly added to the solution, followed by stirring at room temperature for 24 hours. After the reaction was completed, the reaction solution was neutralized to about pH 7 with 5% hydrochloric acid solution, followed by extraction with ethyl acetate and drying to obtain the following compound 8.
0.6 g (0.0008 mole) of bis (triphenylphosphine) palladium (II) dichloride, Pd (PPh3) 2Cl2), 10 g (0.012 mole) of the synthesized polymer, (0.0008 mol) of copperiodide, 0.44 g (0.0016 mol) of triphenylphosphine, and 36 mL of triethylamine were dissolved in 60 mL of tetrahydrofuran. 3.5 g of ethynyltrimethylsilane was added thereto, followed by stirring at 80 ° C for 3 hours. After completion of the reaction, the reaction product was purified by filtration using silica gel. 12.5 g (1 equivalent) of the purified solid was dissolved in 250 mL of a MeOH / THF (volume ratio = 1/2) solution, to which 20 g of potassium carbonate (7 equivalents) was added and stirred at room temperature for 6 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and reduced in pressure to obtain the compound represented by Formula 3-3.
[Formula 3-3]
Synthetic example 4
In a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube, 40 g (0.172 mol) of methoxypylene and 17.48 g (0.086 mol) of terephthaloyl chloride were placed in 300 g of 1,2-dichloroethane, I poured it. After 15 minutes, 25.26 g (0.189 mol) of trichloroaluminum was slowly added, and the reaction solution was reacted at room temperature for 5 hours. After completion of the reaction, trichloroaluminum was removed using water and then concentrated using an evaporator.
Then, 41.78 g (0.21 mol) of 1-dodecanethiol, 15.46 g (0.27 mol) of potassium hydroxide and 230 g of N, N-dimethylformamide were added to 40.96 g (0.068 mol) Followed by stirring at 120 DEG C for 8 hours. The mixture was then cooled, neutralized to pH 7 with 5% hydrogen chloride solution, extracted with ethyl acetate and dried.
160 g of tetrahydrofuran was added to the obtained compound to obtain a solution state. An aqueous solution of 32 g (0.84 mol) of sodium borohydride was slowly added to this solution, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, the reaction mixture was acidified to pH 5 with a 7% hydrogen chloride solution, extracted with ethyl acetate, and the organic solvent was reduced in pressure.
0.6 g (0.0008 mol) of bis (triphenylphosphine) palladium (II) dichloride, Pd (PPh 3 ) 2 Cl 2 ) and 10 g (0.017 mol) 0.16 g (0.0008 mol) of copperiodide, 0.44 g (0.0016 mol) of triphenylphosphine and 36 mL of triethylamine were dissolved in 60 mL of tetrahydrofuran. 3.5 g of ethynyltrimethylsilane was added thereto, followed by stirring at 80 ° C for 3 hours. After completion of the reaction, the reaction product was purified by filtration using silica gel. 12.5 g (1 equivalent) of the purified solid was dissolved in 250 mL of a MeOH / THF (volume ratio = 1/2) solution, to which 20 g of potassium carbonate (7 equivalents) was added and stirred at room temperature for 6 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and reduced in pressure to obtain a compound represented by Formula 3-4.
[Chemical Formula 3-4]
Synthetic example 5
20 g (0.1 mol) of pyrene and 34 g (0.2 mol) of methoxybenzoyl chloride are placed in 312 g of dichloroethane in a 500 ml two-necked flask equipped with a mechanical stirrer and a cooling tube and agitated well. After 15 minutes, 29.2 g (0.22 mol) of trichloro aluminum was slowly added, and the reaction was carried out at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into methanol, and the precipitated material was filtered to remove trichloroaluminum. The thus-filtered powder was placed in a 500 ml two-necked flask equipped with a cooling tube in a mechanical stirrer, and 91 g (0.45 mol) of 1-dodecan sulfate and 30 g (0.54 mol) of potassium hydroxide and 262 g of N, N- And the mixture was stirred at 100 ° C for 5 hours. After completion of the reaction, the reaction product was cooled, and the reaction product was neutralized to pH 5 with 7% hydrogen chloride solution, and the precipitate formed was filtered. The filtered material was dried in a vacuum oven to remove moisture.
The thus-obtained powder was further added with 160 g of THF to obtain a solution state. An aqueous solution of 16 g (0.42 mol) of sodium borohydride was slowly added to this solution, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, the solution was acidified to pH> 5 with 7% hydrogen chloride solution, extracted with ethyl acetate and the organic solvent was reduced in pressure to give 15 g of acetonitrile / ENMP (CH3CN / NMP = 1 / To prepare a solution. To this solution, 3 g (0.022 mol) of hydrogenated potassium carbonate and 3.8 g (0.022 mol) of 4-nitropthalonitrile were added and the mixture was stirred at 85 ° C for 5 hours. After the reaction has been completed, the solution is acidified to pH5> 5 with 7% hydrogen chloride solution, and the resulting precipitate is filtered. The filter powder thus obtained is dried in a vacuum oven to remove moisture. The water-removed powder was further added with 16 g of THF to form a solution state. An aqueous solution of 0.8 g (0.021 mol) of sodium borohydride was slowly added to this solution, and the mixture was stirred at room temperature for 12 hours. The reaction solution was acidified with 7% hydrogen chloride solution to pH > 5, extracted with ethyl acetate, and the organic solvent was reduced to obtain the compound represented by Formula 3-5.
[Formula 3-5]
Preparation of hard mask composition
Examples 1 to 9 and Comparative Example 1
The polymer and the monomer were dissolved in a solvent of propylene glycol monomethyl ether acetate (PGMEA) and filtered to prepare a hard mask composition.
The composition of the polymer and the monomer is shown in Table 1 below.
Evaluation 1: Planarization characteristics
The composition shown in Table 1 was spin-on coated on a silicon wafer having a pattern (trench width 10 μm, trench depth 100 nm), baked to form a thin film, and the cross section was observed using a V-SEM apparatus.
The solid content in the hard mask composition was controlled such that the thickness of the composition on the bare wafer was first annealed at 180 캜 for 120 seconds and then 2000 캜 after the second annealing at 400 캜 for 120 seconds. The hard mask composition was spin-on coated and then the thin film was subjected to a first heat treatment at 180 ° C for 120 seconds and then a second heat treatment at 400 ° C for 120 seconds.
The planarization characteristic is measured by observing the difference in film thickness (that is, step difference) between the hole-portion and the hole-free portion. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an enlarged cross-sectional view of an arbitrary pattern in a silicon wafer coated with a coating liquid. FIG. The thickness indicated by an arrow in Fig. 1 corresponds to a step difference.
The planarization property is superior as the difference (step difference) between the film thickness of the patterned portion and the thickness of the non-patterned portion is smaller. Therefore, the smaller the numerical value, the better the planarization characteristic. The results are shown in Table 2.
Referring to Table 2, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 9 is superior in the level of planarization compared with the thin film formed from the hard mask composition according to Comparative Example 1.
Evaluation 2: Thickness Uniformity
On the silicon wafer, the hard mask composition according to Examples 1 to 9 and Comparative Example 1 was spin-on coated with the hard mask composition on a 12-inch silicon wafer, and then the thin film was subjected to a first heat treatment at 180 ° C for 120 seconds, For 120 seconds. The content of the solid content was adjusted so that the thickness of the thin film after the second heat treatment was 2,000 Å.
As shown in Fig. 2, Uniformity was selected from 19 points, and the thin film thickness was measured at each of these 19 points, and then calculated according to the following equation (2). The thickness of the thin film was measured using K-MAC equipment. The results are shown in Table 3.
[Equation 2]
Uniformity (%) = (maximum thickness of the thin film at 19 points - minimum thickness of the thin film at 19 points) / (average thickness of the thin film at 19 points) X 100
Referring to Table 3, it can be seen that the thin film formed from the hard mask composition according to Examples 1 to 9 above is superior in thickness uniformity to the thin film formed from the hard mask composition according to Comparative Example 1. [
Evaluation 3: Coating property
On the silicon wafer, the hard mask composition according to Examples 1 to 9 and Comparative Example 1 was spin-on coated with the hard mask composition, followed by a first heat treatment at 180 캜 for 120 seconds, followed by a second heat treatment at 400 캜 for 120 seconds To form a thin film. The content of the solid content was adjusted so that the thickness of the thin film after the second heat treatment was 2,000 Å.
The surface of the thin film was observed with an electron microscope. The results are shown in Table 4 below.
As shown in Table 4, the thin films formed from the hard mask compositions according to Examples 1 to 9 were excellent in coating property as compared with the thin films formed from the hard mask composition according to Comparative Example 1.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.
Claims (18)
A monomer represented by the following formula (3), and
menstruum
Containing
Organic film composition:
[Chemical Formula 1]
In Formula 1,
A is a substituted or unsubstituted aromatic ring-containing group, a substituted or unsubstituted heteroaromatic ring-containing group, or a combination thereof,
B is a divalent organic group,
Wherein at least one of A and B is substituted by a functional group comprising a moiety represented by the following formula:
(2)
In Formula 2,
Z is hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
* Is the connection point:
(3)
In Formula 3,
A 0 , A 1 and A 2 are each independently a substituted or unsubstituted aromatic ring-containing group,
At least one of A 0 , A 1 and A 2 contains at least one functional group represented by the following formula (4-1) or (4-2)
L 1 , L 2 , L 3 and L 4 are each independently a single bond, a substituted or unsubstituted C1 to C6 alkylene group, a substituted or unsubstituted C6 to C30 arylene group,
X 1 , X 2 , X 3 and X 4 are each independently hydrogen, a hydroxy group, a substituted or unsubstituted amino group, a halogen atom, or a combination thereof, X 1 and X 2 can not be hydrogen at the same time, X 3 and X 4 can not simultaneously be hydrogen,
m and n are each independently an integer of 0 to 2, the sum of m and n is 1 or more,
Provided that when m is 0, at least one of A 0 and A 2 contains at least one functional group represented by the following formula 4-1 or 4-2 in its structure, and when n is 0, A 0 and A 1 contains at least one functional group represented by the following formula (4-1) or (4-2) in its structure:
[Formula 4-1]
In the above formula (4-1)
W is O, S, NR a or CR b R c , wherein R a to R c are each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a halogen atom, a halogen-containing group,
Y is a substituted or unsubstituted amine group, an azide group, a nitrile group, or a combination thereof,
a is 0 or 1,
b is an integer of 0 to 10,
* Is the connection point:
[Formula 4-2]
In Formula 4,
W is O,
Y is a substituted or unsubstituted vinyl group, a substituted or unsubstituted acetylene group, or a combination thereof,
a is 1,
b is an integer of 0 to 10,
* Is the connection point.
Wherein the functional group having a moiety represented by Formula 2 is represented by the following Formula 2:
[Formula 2 ']
In the above formula (2 '),
W is O, S, NR a or CR b R c , wherein R a to R c are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-
Z is hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
a is 0 or 1,
b is an integer of 0 to 10,
* Is the connection point.
In Formula 3, A 0 , A 1 and A 2 each independently represent a substituted or unsubstituted moiety selected from the following Group 1:
[Group 1]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.
In Formula 3 A 0, A 1 and A 2 is at least one of the polycyclic ring due to the organic film composition.
Wherein the monomer comprises a substituted or unsubstituted acetylene group, the organic film composition represented by any one of the following formulas (3a) to (3c):
[Chemical Formula 3]
(3b)
[Chemical Formula 3c]
In the above formulas (3a) to (3c)
A 3 , A 4 and A 5 are each independently a substituted or unsubstituted aromatic ring-containing group,
W is O.
Wherein A is a substituted or unsubstituted moiety selected from the following groups 1 and 2:
[Group 1]
[Group 2]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group or a combination thereof,
In the group 2,
Z 1 and Z 2 are each independently NR d , O, S, Te or Se,
Z 3 to Z 5 are N,
R d and R e are each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen atom, a halogen-containing group, a substituted or unsubstituted 1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, It is a combination.
Wherein B is an organic film composition represented by any one of the following formulas Z1 to Z4:
(Z1)
(Z2)
(Z3)
(Z4)
In the above general formulas Z1 to Z4,
e and f are each independently 0 or 1,
g is an integer of 1 to 5,
Y 1 to Y 4 are each independently any one of a substituted or unsubstituted moiety selected from the following Group 3,
* Is the connection point:
[Group 3]
In the group 3,
M, M 'and M "are each independently a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2, CR f R g, NR h, or carbonyl, wherein R f to R h are each Independently, hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof,
L 1 is a substituted or unsubstituted C6 to C50 arylene group, a substituted or unsubstituted C1 to C10 alkylene oxide-containing group, or a combination thereof,
r is an integer from 0 to 10,
s is an integer of 0 to 10,
k is an integer of 0 to 3;
Wherein the polymer further comprises a structural unit represented by the following formula (5): < EMI ID =
[Chemical Formula 5]
In Formula 5,
X 0 is a substituted or unsubstituted aromatic ring-containing group, a substituted or unsubstituted heteroaromatic ring-containing group, or a combination thereof,
L 0 is a divalent organic group,
* Is the connection point.
Wherein X 0 is a substituted or unsubstituted moiety selected from the following groups 1 and 2:
[Group 1]
[Group 2]
In the group 1,
X is a substituted or unsubstituted C1 to C10 alkylene group, O, S, SO 2 , CR f R g , NR h , or carbonyl, wherein R f to R h are each independently hydrogen, A C1 to C10 alkyl group, a halogen atom, a halogen-containing group or a combination thereof,
In the group 2,
Z 1 and Z 2 are each independently NR d , O, S, Te or Se,
Z 3 to Z 5 are N,
R d and R e are each independently selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, an ethoxy group, a halogen atom, a halogen-containing group, a substituted or unsubstituted 1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, It is a combination.
Wherein the polymer comprises at least one oxygen atom in its structural unit.
Wherein the monomer has a molecular weight of 500 to 50,000.
Wherein the polymer has a weight average molecular weight of 500 to 200,000.
Wherein the weight ratio of the polymer and the monomer is 70:30 to 30:70.
Applying the organic film composition according to any one of claims 1 to 4 and 6 to 14 on the material layer,
Heat treating the organic film composition to form a hard mask layer,
Forming a silicon-containing thin film layer on the hard mask layer,
Forming a photoresist layer on the silicon-containing thin film layer,
Exposing and developing the photoresist layer to form a photoresist pattern,
Selectively removing the silicon-containing thin film layer and the hard mask layer using the photoresist pattern and exposing a portion of the material layer, and
Etching the exposed portion of the material layer
≪ / RTI >
Wherein the step of applying the organic film composition is performed by a spin-on coating method.
Wherein the heat treatment includes a first heat treatment performed at 50 ° C to 250 ° C, and a second heat treatment subsequent to the first heat treatment and proceeding at 200 ° C to 500 ° C.
Further comprising forming a bottom anti-reflective layer (BARC) before the step of forming the photoresist layer.
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| KR1020160142173A KR101988997B1 (en) | 2016-10-28 | 2016-10-28 | Polymer, organic layer composition, and method of forming patterns |
| PCT/KR2016/015411 WO2018079937A1 (en) | 2016-10-28 | 2016-12-28 | Organic film composition and pattern formation method |
| TW106112724A TWI644999B (en) | 2016-10-28 | 2017-04-17 | Polymer, organic layer composition, and method of forming patterns |
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| JP7368322B2 (en) * | 2020-06-12 | 2023-10-24 | 信越化学工業株式会社 | Resist underlayer film material, pattern forming method, and resist underlayer film forming method |
| KR20230040147A (en) * | 2021-09-15 | 2023-03-22 | 삼성에스디아이 주식회사 | Hardmask composition, hardmask layer and method of forming patterns |
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| JP2002322271A (en) | 2001-04-25 | 2002-11-08 | Nippon Shokubai Co Ltd | Polyether ketone and method for producing the same |
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| JP4877101B2 (en) * | 2007-07-02 | 2012-02-15 | Ｊｓｒ株式会社 | Resist underlayer film forming composition and pattern forming method |
| US8513133B2 (en) * | 2011-03-31 | 2013-08-20 | Jsr Corporation | Composition for forming resist underlayer film and method for forming pattern |
| KR101566533B1 (en) * | 2012-10-24 | 2015-11-05 | 제일모직 주식회사 | Hardmask composition and method of forming patterns using the hardmask composition |
| KR101684978B1 (en) * | 2013-06-27 | 2016-12-09 | 제일모직 주식회사 | Hardmask composition, method of forming patterns using the hardmask composition and semiconductor integrated circuit device including the patterns including the patterns |
| KR101754901B1 (en) * | 2014-05-16 | 2017-07-06 | 제일모직 주식회사 | Hardmask composition and method of forming patterns using the hardmask composition |
| JP6641879B2 (en) * | 2015-03-03 | 2020-02-05 | Jsr株式会社 | Composition for forming resist underlayer film, method for producing resist underlayer film and patterned substrate |
| US20170137663A9 (en) * | 2015-03-03 | 2017-05-18 | Jsr Corporation | Composition for resist underlayer film formation, resist underlayer film, and production method of patterned substrate |
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| JP2002322271A (en) | 2001-04-25 | 2002-11-08 | Nippon Shokubai Co Ltd | Polyether ketone and method for producing the same |
| JP2016044272A (en) | 2014-08-25 | 2016-04-04 | Jsr株式会社 | Composition for forming film, film and manufacturing method and compound of substrate having formed pattern |
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