JP2019523985A - ハードマスク組成物 - Google Patents
ハードマスク組成物 Download PDFInfo
- Publication number
- JP2019523985A JP2019523985A JP2018562117A JP2018562117A JP2019523985A JP 2019523985 A JP2019523985 A JP 2019523985A JP 2018562117 A JP2018562117 A JP 2018562117A JP 2018562117 A JP2018562117 A JP 2018562117A JP 2019523985 A JP2019523985 A JP 2019523985A
- Authority
- JP
- Japan
- Prior art keywords
- hard mask
- resin
- mask composition
- fullerene
- organic sulfonic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 102
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 16
- 229910003472 fullerene Inorganic materials 0.000 claims description 46
- -1 amine salts Chemical class 0.000 claims description 45
- 229920005989 resin Polymers 0.000 claims description 29
- 239000011347 resin Substances 0.000 claims description 29
- 150000001993 dienes Chemical class 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 20
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 150000003949 imides Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 claims description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000006352 cycloaddition reaction Methods 0.000 claims description 13
- 229920003986 novolac Polymers 0.000 claims description 13
- 239000002243 precursor Substances 0.000 claims description 13
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000003460 sulfonic acids Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000007115 1,4-cycloaddition reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- KFUSXMDYOPXKKT-VIFPVBQESA-N (2s)-2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OC[C@H]1OC1 KFUSXMDYOPXKKT-VIFPVBQESA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 5
- 229920000877 Melamine resin Polymers 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 4
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical group C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004640 Melamine resin Substances 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 229920000180 alkyd Polymers 0.000 claims description 4
- 125000003147 glycosyl group Chemical group 0.000 claims description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 125000005409 triarylsulfonium group Chemical group 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 241000894007 species Species 0.000 claims 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 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims 2
- FHCLGDLYRUPKAM-UHFFFAOYSA-N 1,2,3-tribromopropane Chemical compound BrCC(Br)CBr FHCLGDLYRUPKAM-UHFFFAOYSA-N 0.000 claims 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 125000002877 alkyl aryl group Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229950005228 bromoform Drugs 0.000 claims 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 1
- 229940116333 ethyl lactate Drugs 0.000 claims 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 229940078552 o-xylene Drugs 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 239000010409 thin film Substances 0.000 description 29
- 238000009472 formulation Methods 0.000 description 26
- 239000000463 material Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical compound C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 description 5
- 150000003003 phosphines Chemical class 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- HCHUFGAAOWSTPH-UHFFFAOYSA-N 2,3-dimethylidenenaphthalene Chemical compound C1=CC=CC2=CC(=C)C(=C)C=C21 HCHUFGAAOWSTPH-UHFFFAOYSA-N 0.000 description 3
- UDWSMTLOPYNMMD-UHFFFAOYSA-N 2,3-dimethylidenephenanthrene Chemical compound C=C1C=C2C=CC3=CC=CC=C3C2=CC1=C UDWSMTLOPYNMMD-UHFFFAOYSA-N 0.000 description 3
- YIZIAAIMKUQBDD-UHFFFAOYSA-N 2,3-dimethylidenepyridine Chemical compound C=C1C=CC=NC1=C YIZIAAIMKUQBDD-UHFFFAOYSA-N 0.000 description 3
- 229920003270 Cymel® Polymers 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 125000002897 diene group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000009616 inductively coupled plasma Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- JJPKWNXRUDKBQT-UHFFFAOYSA-N 2,4-bis(trichloromethyl)-6-[2-(3,4,5-trimethoxyphenyl)ethenyl]-1,3,5-triazine Chemical compound COC1=C(OC)C(OC)=CC(C=CC=2N=C(N=C(N=2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)=C1 JJPKWNXRUDKBQT-UHFFFAOYSA-N 0.000 description 2
- CWQZLVPKEVXEOB-UHFFFAOYSA-N 2-(tribromomethyl)-1,3,5-triazine Chemical compound BrC(Br)(Br)C1=NC=NC=N1 CWQZLVPKEVXEOB-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical class [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001334 alicyclic compounds Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 238000001020 plasma etching Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
(式中、nが1乃至12の整数であり、Qが60、70、76、78、80、82、84、86、90、92、94または96個の炭素原子を有するフラーレンであり、Pが、4乃至6員を有する単一の非架橋の環、または、各々が4乃至12員を有する2以上の非架橋の縮合環を含む)で表される、1または複数のエキソヘドラル環(exohedral rings)を有する1または複数のフラーレン誘導体を含み、さらに、2以上の熱的または触媒的反応基を含む架橋剤を含み、前記エキソヘドラル(exohedral)第1の環であるPおよび前記第2の環の両方が任意選択的に少なくとも1つのヘテロ原子を含んでよいことを特徴とするハードマスク組成物が開示される。
(式中、nが1乃至12の整数であり、フラーレン中の炭素原子の数であるQが60、70、76、78、80、82、84、86、90、92、94、または96であり、R1、R2、R3、R4が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R5およびR6が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)で表される1または複数のフラーレン誘導体;および(b)2以上の熱的または触媒的反応基を含む架橋剤を含むことを特徴とするハードマスク組成物が開示される。
(式中、R7およびR8が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R9およびR10が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)で表されることを特徴とするハードマスク組成物が開示される。すぐ上の組成物に関しては、nは1乃至6の整数であり、フラーレン中の炭素原子の数であるQは、60、70、76、78、80、82、84、86、90、92、94、または96炭素原子である。
(式中、IVがフラーレンであり、Vがジエンまたはその前駆体を表し、nが1乃至20の整数であり、前記フラーレン中の炭素原子の数であるQが60、70、76、78、80、82、84、86、90、92、94、または96であり、R1、R2、R3、およびR4が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R5およびR6が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)として特徴付けられるフラーレン誘導体;および(b)2以上の熱的または触媒的反応基を含む架橋剤を含むことを特徴とするハードマスク組成物が開示される。
(式中、(VI)がフラーレンであり、(VII)がジエンまたはその前駆体を表し、R7およびR8が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R9およびR10が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)として特徴付けられることを特徴とするハードマスク組成物が開示される。上記の組成物に関しては、nは1乃至20の整数であり、フラーレン中の炭素原子の数であるQは60、70、76、78、80、82、84、86、90、92、94、または96である。
C60はフラーレンであり、(X)はジエン前駆体であり、(XI)は[4+2]環化付加反応の生成物であり、(XII)は[3+2]環化付加反応の生成物である。理論によって縛られることを意図するものではないが、これら2種の生成物は異なった中間体を通じて得られると確信されている。例えば、単一の脱離反応を通じたジエン中間体の生成は、[4+2]環化付加に至ってよく、ジエン前駆体は、(X)に示すように、脱ハロゲン化水素、脱水等のような単一脱離反応によって失われると確信されている水酸基を含んでよく;これによってジエン反応物質を形成する。水酸基に加えて、他の基も十分な反応性を備えてよい。ここで脱離基と表記されるこれらの基は、水酸基のカルボン酸エステル、スルホン酸エステル、ホスフィン酸エステル、アルキル、tert−アルキル、アルキル−アリールカルボン酸エステル、ハロゲン、シアン化物、イソシアニド、シアネート、イソシアネート、チオシアネート、イソチオシアネート、ヒポチオシアネート(hypothiocyanite)、セレノシアネート、アジ化物、トリニトロメタニド、およびトリシアノメタニド等を含んでよいが、これらに限定されない。
Claims (20)
- ハードマスク組成物であって、一般式:
(式中、nが1乃至12の整数であり、Qが60、70、76、78、80、82、84、86、90、92、94または96個の炭素原子を有するフラーレンであり、Pが、4乃至6員を有する単一の非架橋の環、または、各々が4乃至12員を有する2以上の非架橋の縮合環を含む)
で表される、1または複数のエキソヘドラル環(exohedral rings)を有する1または複数のフラーレン誘導体を含み、さらに、2以上の熱的または触媒的反応基を含む架橋剤を含み、前記エキソヘドラル(exohedral)第1の環であるPおよび前記第2の環の両方が任意選択的に少なくとも1つのヘテロ原子を含んでよいことを特徴とするハードマスク組成物。 - 請求項1に記載のハードマスク組成物において、前記1または複数のエキソヘドラル環(exohedral rings)を有する1または複数のフラーレン誘導体が、一般式:
(式中、R1、R2、R3、R4が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R5およびR6が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)
で表されることを特徴とするハードマスク組成物。 - 請求項2に記載のハードマスク組成物において、前記架橋剤が、4,4’−(9H−フルオレン−9,9−ジイル)ジアニリン、エポキシフェノール性ノボラック樹脂、エポキシクレゾール性ノボラック樹脂、エポキシビスフェノールA樹脂、エポキシビスフェノールAノボラック樹脂、エポキシビスフェノールC樹脂、アルキルメチルメラミン樹脂、アルキルメチルグリコールウリル樹脂、アルキルメチルグアナミン樹脂、アルキルメチルベンゾグアナミン樹脂、グリコシル尿素樹脂、またはアルキド樹脂から選択されることを特徴とするハードマスク組成物。
- 請求項2に記載のハードマスク組成物が、1または複数の熱酸発生剤(thermal acid generators)をさらに含み、前記1または複数の熱酸発生剤が、有機スルホン酸のアルキルエステル、有機スルホン酸の脂環式エステル、有機スルホン酸のアミン塩、有機スルホン酸の2−ニトロベンジルエステル、有機スルホン酸の4−ニトロベンジルエステル、有機スルホン酸のベンゾインエステル、有機スルホン酸のβ−ヒドロキシアルキルエステル、有機スルホン酸のβ−ヒドロキシシクロアルキルエステル、有機スルホン酸のトリアリールスルホニウム塩、有機スルホン酸のアルキルジアリールスルホニウム塩、有機スルホン酸のジアルキルアリールスルホニウム塩、有機スルホン酸のトリアルキルスルホニウム塩、有機スルホン酸のジアリールヨードニウム塩、有機スルホン酸のアルキルアリールスルホニウム塩、またはトリス(オルガノスルホニル)メチドのアンモニウム塩から選択されることを特徴とするハードマスク組成物。
- 請求項2に記載のハードマスク組成物において、前記1または複数のエキソヘドラル環(exohedral rings)を有する1または複数のフラーレン誘導体が、式:
(式中、R7およびR8が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R9およびR10が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)
で表されることを特徴とするハードマスク組成物。 - 請求項5に記載のハードマスク組成物において、R1、R2、R3、R4、R7、R8、R9、およびR10の各々が水素原子を表すことを特徴とするハードマスク組成物。
- 請求項6に記載のハードマスク組成物において、前記1または複数のフラーレン誘導体がブレンドを含み、前記ブレンドがQが60、Qが70、nが2乃至8である種を含むことを特徴とするハードマスク組成物。
- 請求項2に記載のハードマスク組成物において、前記1または複数のフラーレン誘導体がブレンドを含み、前記ブレンドがQが60、Qが70、nが2乃至8である種を含むことを特徴とするハードマスク組成物。
- 請求項6に記載のハードマスク組成物において、前記架橋剤が、ポリ(o−クレシルグリシジルエーテル)ホルムアルデヒド共重合体を含むことを特徴とするハードマスク組成物。
- 請求項2に記載のハードマスク組成物において、ポリエチレングリコールモノメチルエーテルアセテート、エチルラクテート、アニソール、シクロヘキサノン、トルエン、クロロホルム、クロロベンゼン、o−ジクロロベンゼン、m−ジクロロベンゼン、p−ジクロロベンゼン、o−キシレン、m−キシレン、p−キシレン、カーボンジスルフィド、1−クロロナフタレン、1−メチルナフタレン、1,2,4−トリメチルベンゼン、テトラヒドロナフタレン、1,2,3−トリブロモプロパン、ブロモホルム、クメン、ベンゼン、四塩化炭素、クロロホルム、n−ヘキサン、シクロヘキサン、テトラヒドロフラン、アセトニトリル、メタノール、水、ペンタン、ヘプタン、オクタン、イソオクタン、デカン、ドデカン、テトラデカン、アセトン、イソプロパノール、ジオキサン、メシチレン、ジクロロメタン、または上記の何れかを含む混合物から選択される1または複数の溶媒をさらに含むことを特徴とするハードマスク組成物。
- ハードマスク組成物であって、
a.1または複数のフラーレン誘導体であって、前記フラーレンとジエンまたはジエン前駆体との間の環化付加反応の産物として生成され、
(式中、Vがフラーレンであり、VIがジエンまたはその前駆体を表し、nが1乃至12の整数であり、前記フラーレン中の炭素原子の数であるQが60、70、76、78、80、82または84であり、R1、R2、R3、およびR4が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R5およびR6が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)
として特徴付けられるフラーレン誘導体;および
b.2以上の熱的または触媒的反応基を含む架橋剤
を含むことを特徴とするハードマスク組成物。 - 請求項11に記載のハードマスク組成物において、前記環化付加反応が[4+2]環化付加反応であることを特徴とするハードマスク組成物。
- 請求項11に記載のハードマスク組成物において、前記フラーレンとジエンまたはジエン前駆体との間の前記環化付加反応が
(式中、R7およびR8が独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を表し、R9およびR10が共に非架橋環構造を含み、または代替的に独立して、エステル、アルコール、フェノール、アミン、アミド、イミド、またはカルボン酸、水素、ハロゲン、C6−C20アリール基、C1−C20アルキル基、またはC1−C20塩基性基を含む置換基を含む)
として特徴付けられることを特徴とするハードマスク組成物。 - 請求項13に記載のハードマスク組成物において、R1、R2、R3、R4、R7、R8、R9、およびR10の各々が水素原子を表すことを特徴とするハードマスク組成物。
- 請求項14に記載のハードマスク組成物において、前記1または複数のフラーレン誘導体がブレンドを含み、前記ブレンドがQが60、Qが70、nが2乃至8である種を含むことを特徴とするハードマスク組成物。
- 請求項13に記載のハードマスク組成物において、前記1または複数のフラーレン誘導体がブレンドを含み、前記ブレンドがQが60、Qが70、nが2乃至8である種を含むことを特徴とするハードマスク組成物。
- 請求項13に記載のハードマスク組成物において、前記架橋剤が、4,4’−(9H−フルオレン−9,9−ジイル)ジアニリン、エポキシフェノール性ノボラック樹脂、エポキシクレゾール性ノボラック樹脂、エポキシビスフェノールA樹脂、エポキシビスフェノールAノボラック樹脂、エポキシビスフェノールC樹脂、アルキルメチルメラミン樹脂、アルキルメチルグリコールウリル樹脂、アルキルメチルグアナミン樹脂、アルキルメチルベンゾグアナミン樹脂、グリコシル尿素樹脂、またはアルキド樹脂から選択されることを特徴とするハードマスク組成物。
- 請求項11に記載のハードマスク組成物において、前記架橋剤が、4,4’−(9H−フルオレン−9,9−ジイル)ジアニリン、エポキシフェノール性ノボラック樹脂、エポキシクレゾール性ノボラック樹脂、エポキシビスフェノールA樹脂、エポキシビスフェノールAノボラック樹脂、エポキシビスフェノールC樹脂、アルキルメチルメラミン樹脂、アルキルメチルグリコールウリル樹脂、アルキルメチルグアナミン樹脂、アルキルメチルベンゾグアナミン樹脂、グリコシル尿素樹脂、またはアルキド樹脂から選択されることを特徴とするハードマスク組成物。
- 請求項17に記載のハードマスク組成物において、前記架橋剤が、ポリ(o−クレシルグリシジルエーテル)ホルムアルデヒド共重合体を含むことを特徴とするハードマスク組成物。
- 請求項18に記載のハードマスク組成物において、前記架橋剤が、ポリ(o−クレシルグリシジルエーテル)ホルムアルデヒド共重合体を含むことを特徴とするハードマスク組成物。
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JP2012042895A (ja) * | 2010-08-23 | 2012-03-01 | Shin Etsu Chem Co Ltd | レジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法、フラーレン誘導体 |
JP2015513786A (ja) * | 2012-02-10 | 2015-05-14 | ザ ユニバーシティ オブ バーミンガム | スピンオンハードマスク材料 |
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US20170345669A1 (en) | 2017-11-30 |
KR20190035622A (ko) | 2019-04-03 |
US10438808B2 (en) | 2019-10-08 |
CN109562944B (zh) | 2022-09-09 |
JP7055106B2 (ja) | 2022-04-15 |
CN109562944A (zh) | 2019-04-02 |
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WO2017205272A1 (en) | 2017-11-30 |
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