WO2010147155A1 - カルバゾールノボラック樹脂 - Google Patents
カルバゾールノボラック樹脂 Download PDFInfo
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- WO2010147155A1 WO2010147155A1 PCT/JP2010/060223 JP2010060223W WO2010147155A1 WO 2010147155 A1 WO2010147155 A1 WO 2010147155A1 JP 2010060223 W JP2010060223 W JP 2010060223W WO 2010147155 A1 WO2010147155 A1 WO 2010147155A1
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title description 60
- 229920005989 resin Polymers 0.000 title description 37
- 239000011347 resin Substances 0.000 title description 37
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- 239000000203 mixture Substances 0.000 claims abstract description 126
- 229920000642 polymer Polymers 0.000 claims abstract description 112
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000004065 semiconductor Substances 0.000 claims abstract description 52
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- 239000000758 substrate Substances 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 238000005530 etching Methods 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 238000010894 electron beam technology Methods 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 238000012545 processing Methods 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000011161 development Methods 0.000 claims description 8
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- 238000000151 deposition Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 description 254
- -1 t- Butyl Chemical group 0.000 description 166
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- 238000003786 synthesis reaction Methods 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000002904 solvent Substances 0.000 description 30
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 26
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- 238000006116 polymerization reaction Methods 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 21
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- 238000001459 lithography Methods 0.000 description 19
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000010409 thin film Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 239000004698 Polyethylene Substances 0.000 description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 229920000573 polyethylene Polymers 0.000 description 14
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- 239000004094 surface-active agent Substances 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- 229920002120 photoresistant polymer Polymers 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 238000002834 transmittance Methods 0.000 description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 10
- 238000010586 diagram Methods 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 239000010703 silicon Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 150000001716 carbazoles Chemical class 0.000 description 8
- 238000001226 reprecipitation Methods 0.000 description 8
- 125000006617 triphenylamine group Chemical class 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 0 CC=C(C1=CC(I)=C)N(*)C2=C1C(C)=IC=C2 Chemical compound CC=C(C1=CC(I)=C)N(*)C2=C1C(C)=IC=C2 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000004682 monohydrates Chemical class 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 239000006254 rheological additive Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004147 Sorbitan trioleate Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
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- 239000000654 additive Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 229930003836 cresol Natural products 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
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- 239000003960 organic solvent Substances 0.000 description 3
- 229920003190 poly( p-benzamide) Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 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 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
- 235000019337 sorbitan trioleate Nutrition 0.000 description 3
- 229960000391 sorbitan trioleate Drugs 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 229920002554 vinyl polymer Chemical class 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- CSZZMFWKAQEMPB-UHFFFAOYSA-N 1-methoxybutan-2-ol Chemical compound CCC(O)COC CSZZMFWKAQEMPB-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- SDFLTYHTFPTIGX-UHFFFAOYSA-N 9-methylcarbazole Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C2=C1 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- ZRIRUWWYQXWRNY-UHFFFAOYSA-N CC(C)(c(cc1CO)cc(CO)c1O)c(cc1CO)cc(CO)c1O Chemical compound CC(C)(c(cc1CO)cc(CO)c1O)c(cc1CO)cc(CO)c1O ZRIRUWWYQXWRNY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KUMMBDBTERQYCG-UHFFFAOYSA-N Cc(cc1CO)cc(CO)c1O Chemical compound Cc(cc1CO)cc(CO)c1O KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising 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
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
Definitions
- the present invention relates to a carbazole novolak resin containing a specific structure. Furthermore, the present invention relates to a resist underlayer film forming composition containing the carbazole novolak resin, a resist underlayer film formed therefrom, a resist pattern forming method using the resist underlayer film forming composition, and a method for manufacturing a semiconductor device. The present invention also relates to a high refractive index film-forming composition containing the carbazole novolak resin, a high refractive index film having transparency in the visible region, and an electronic device including the high refractive index film.
- a fine processing method of a semiconductor substrate a resist film formed from a photoresist composition is formed on a substrate to be processed such as a silicon wafer, and a mask on which a pattern for transferring to a semiconductor device is drawn on the resist film Irradiating actinic rays such as ultraviolet rays through the pattern, developing and patterning the resist thin film, etching the processed substrate such as a silicon wafer using the resulting photoresist pattern as a protective film, and transferring the pattern to the substrate Processing methods are known.
- a resist underlayer film for such a process unlike a resist underlayer film having a high etching rate (high etching rate), compared to a resist underlayer film and a resist having a dry etching rate selection ratio close to that of a resist.
- a resist underlayer film having a low dry etching rate selectivity or a resist underlayer film having a dry etching rate selectivity lower than that of a semiconductor substrate is used.
- a resist underlayer film forming composition containing various polymers for forming the resist underlayer film is known.
- a resist underlayer film forming composition containing polyvinyl carbazole see Patent Document 1, Patent Document 2, and Patent Document 3
- a resist underlayer film forming composition containing a fluorenephenol novolak resin for example, see Patent Document 4
- Resist underlayer film forming composition containing fluorene naphthol novolak resin see, for example, Patent Document 5
- resist underlayer film forming composition containing a resin having fluorenephenol and arylalkylene as repeating units for example, Patent Document 6, Patent Document 7
- a novolak resin see Patent Document 8 using carbazole and acetaldehyde having high heat resistance used for an insulating material such as a printed wiring board is disclosed.
- JP-A-2-293850 Japanese Patent Laid-Open No. 1-154050 JP-A-2-22657 JP 2005-128509 A JP2007-199653A JP2007-178974 U.S. Pat. No. 7,378,217 JP2007-297540
- An object of the present invention is to provide a novel carbazole novolak resin containing a specific structure. Furthermore, the objective of this invention is providing the resist underlayer film forming composition containing the carbazole novolak resin for using for the lithography process of semiconductor device manufacture. Furthermore, an object of the present invention is to select a dry etching rate close to that of a resist by flattening the substrate formed from the resist underlayer film forming composition and obtaining an excellent resist pattern without causing intermixing with the resist.
- the ratio of the dry etching rate is smaller than that of the resist and the semiconductor substrate, and the reflected light from the substrate is effectively used when irradiation light having a wavelength of 248 nm, 193 nm, 157 nm or the like is used for fine processing of the resist.
- An object is to provide a resist underlayer film that has the ability to absorb and has heat resistance against high-temperature processing in substrate processing such as formation of a resist layer or formation of a hard mask. Furthermore, the objective of this invention is providing the formation method of a resist pattern using said resist underlayer film forming composition. Furthermore, the objective of this invention is providing the manufacturing method of the semiconductor device containing the lithography process using said resist underlayer film forming composition.
- Another object of the present invention is to provide a transparent high refractive index film in the visible region using a unique property of a carbazole novolak resin, a high refractive index film forming composition for forming the same, and the high refractive index film.
- the present invention relates to a polymer having a specific structure shown below, that is, a carbazole novolak resin, a resist underlayer film forming composition containing the same, a resist underlayer film formed therefrom, and a method of manufacturing a semiconductor device using the same.
- the present invention also relates to a high refractive index film-forming composition containing the carbazole novolak resin, a high refractive index film formed therefrom, and an electronic device including the same.
- R 1 and R 2 are each a hydrogen atom, a halogen group, a nitro group, an amino group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or carbon.
- R 3 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and combinations thereof, and The alkyl group, the alkenyl group or the aryl group represents a group which may contain an ether bond, a ketone bond or an ester bond;
- R 4 represents an aryl group or heterocyclic group having 6 to 40 carbon atoms which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group
- R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40
- the polymer according to the first aspect including a unit structure in which the carbon atom is the carbon atom at the 9-position of the formed fluorene ring
- the following formula (2) and / or formula (3) are each a hydrogen atom, a halogen group, a nitro group, an amino group, a hydroxy group, or 1 to 10 carbon atoms.
- R 3 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and combinations thereof, and
- the alkyl group, the alkenyl group or the aryl group represents a group which may contain an ether bond, a ketone bond or an ester bond;
- R 4 represents an aryl group or heterocyclic group having 6 to 40 carbon atoms which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group
- R 5 represents a
- R 4 and R 5 together with the carbon atom to which they are attached may form a ring, n1 and n2 are each an integer of 1 to 3, n3 to n5 are integers of 1 to 4, respectively.
- a polymer comprising a unit structure represented by As a fifth aspect, in the formula (2) and / or the formula (3), R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are each a hydrogen atom, and R 4 A polymer according to the fourth aspect, comprising a unit structure which is a phenyl group or a naphthyl group,
- a resist underlayer film forming composition containing the polymer according to any one of the first aspect to the fifth aspect,
- the resist underlayer film forming composition according to the sixth aspect further including a crosslinking agent
- the resist underlayer film forming composition according to the sixth aspect or the seventh aspect further comprising an acid and / or an acid generator, As
- a step of forming a resist underlayer film on a semiconductor substrate with the resist underlayer film forming composition according to any one of the sixth to eighth aspects, and forming a resist film on the resist underlayer film A step of forming a resist pattern on the resist film by irradiating and developing with light or electron beam, a step of etching the lower layer film according to the resist pattern, and a semiconductor substrate is processed using the patterned lower layer film
- a method of manufacturing a semiconductor device including a process As a twelfth aspect, a step of forming a resist underlayer film on a semiconductor substrate with the resist underlayer film forming composition according to any one of the sixth to eighth aspects, and forming a hard mask on the resist underlayer film A step of forming a resist film on the hard mask, a step of forming a resist pattern on the resist film by irradiation and development with light or an electron beam, a step of etching the hard mask according to the resist pattern, the
- the resist underlayer film forming composition of the present invention can form a resist underlayer film that does not cause intermixing with the layer coated thereon. Furthermore, the resist underlayer film forming composition of the present invention can form an excellent resist underlayer film having a dry etching rate selectivity close to that of the resist and a small dry etching rate selectivity compared to the resist and the semiconductor substrate. it can. Furthermore, the resist underlayer film forming composition of the present invention forms a resist underlayer film having high heat resistance even under high temperature conditions such as a heat curing step for resist film formation and a vacuum deposition process for hard mask formation. can do.
- the resist underlayer film forming composition of the present invention contains a polymer containing a skeleton structure capable of absorbing light or electron beams, the resist also has an effect as an antireflection film for preventing reflection of light or electron beams from the substrate.
- An underlayer film can also be formed.
- the resist underlayer film forming composition of the present invention can form a resist underlayer film having sufficient etching resistance against a semiconductor substrate (for example, a thermally oxidized silicon film, a silicon nitride film, a polysilicon film, etc. on the substrate). .
- the resist underlayer film of the present invention can be used as a planarization film, an antireflection film, a resist layer antifouling film, a heat resistant film, a film having dry etch selectivity and etching resistance, a semiconductor device
- resist pattern formation and transfer of the resist pattern onto the semiconductor substrate can be easily and accurately performed.
- it since it has high heat resistance, it can be suitably used for a lithography process for manufacturing a semiconductor device including a step of forming a hard mask by vapor deposition of an inorganic substance.
- the carbazole novolak resin containing the specific structure of the present invention is excellent in transparency and heat resistance in the visible light region, has a high refractive index, and is excellent in solubility in various solvents. Therefore, a high refractive index film-forming composition containing a carbazole novolak resin having a specific structure according to the present invention is used for a protective film of a liquid crystal display element, a TFT array planarizing film, an overcoat such as a color filter, a spacer material, and an EL display.
- a high refractive index film used for a light extraction improving film, a light intake improving layer of an imaging element, a light extraction improving layer of an LED element, and the like can be formed.
- membrane of this invention can be widely used as an optical member of an electronic device.
- FIG. 1 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 1.
- FIG. 2 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 2.
- FIG. 3 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 3.
- FIG. 4 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 4.
- FIG. 5 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 5.
- FIG. 6 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 6.
- FIG. 7 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 7.
- FIG. 8 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 8.
- FIG. 1 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 1.
- FIG. 2 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 2.
- FIG. 3 is a 1 H-NMR spectrum of the
- FIG. 9 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 9.
- FIG. 10 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 10.
- FIG. 11 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 11.
- FIG. 12 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 12.
- FIG. 13 is a 1 H-NMR spectrum of the polymer obtained in Synthesis Example 13.
- FIG. 14 is a 1 H-NMR spectrum of the polymer obtained in Comparative Synthesis Example 1.
- FIG. 15 is a 1 H-NMR spectrum of the polymer obtained in Comparative Synthesis Example 2.
- FIG. 16 shows the light transmittance of the thin film obtained in Example 7.
- FIG. 16 shows the light transmittance of the thin film obtained in Example 7.
- FIG. 17 is a diagram showing the light transmittance of the thin film obtained in Example 8.
- FIG. 18 is a diagram showing the light transmittance of the thin film obtained in Example 9.
- FIG. 19 is a diagram showing the light transmittance of the thin film obtained in Example 10.
- FIG. 20 is a diagram showing the light transmittance of the thin film obtained in Example 11.
- FIG. 21 is a diagram showing the light transmittance of the thin film obtained in Example 12.
- FIG. 22 is a diagram showing the light transmittance of the thin film obtained in Example 13.
- FIG. 23 is a diagram showing the light transmittance of the thin film obtained in Example 14.
- FIG. 24 is a diagram showing the light transmittance of the thin film obtained in Example 15.
- FIG. 25 is a diagram showing the light transmittance of the thin film obtained in Comparative Example 2.
- FIG. 26 is a diagram showing the light transmittance of the thin film obtained in Comparative Example 3.
- the present invention provides a polymer containing a unit structure represented by the above formula (1), or a polymer containing a unit structure represented by the formula (2) and / or the formula (3), that is, a specific structure. Containing carbazole novolac resin.
- R 1 and R 2 are each a hydrogen atom, a halogen group, a nitro group, an amino group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms,
- the alkyl group, the alkenyl group, or the aryl group is selected from the group consisting of an aryl group having 6 to 40 carbon atoms, and combinations thereof, and may include an ether bond, a ketone bond, or an ester bond Groups.
- R 3 includes a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a combination thereof.
- the alkyl group, the alkenyl group, or the aryl group selected from the group include an ether bond, a ketone bond, or an ester bond.
- examples of R 4 include aryl groups or heterocyclic groups having 6 to 40 carbon atoms, which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group.
- R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group, or 6 to 6 carbon atoms. 40 aryl groups or heterocyclic groups may be mentioned.
- R 4 and R 5 may be combined with the carbon atom to which they are bonded to form a ring. Examples of these rings include a fluorene ring formed together with the carbon atom to which R 4 and R 5 are bonded, and the fluorene ring which is the carbon atom at the 9-position of the fluorene ring formed by the carbon atom. It is done.
- n1 and n2 are each an integer of 1 to 3.
- R 1 , R 2 , R 6 , R 7 , and R 8 are each a hydrogen atom, a halogen group, a nitro group, an amino group, a hydroxy group, or a carbon number of 1 to Selected from the group consisting of 10 alkyl groups, alkenyl groups having 2 to 10 carbon atoms, aryl groups having 6 to 40 carbon atoms, and combinations thereof, and the alkyl group, the alkenyl group, or the aryl group is A group which may contain an ether bond, a ketone bond or an ester bond.
- R 3 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Examples of the alkyl group, the alkenyl group, or the aryl group selected from the group consisting of combinations thereof include groups that may include an ether bond, a ketone bond, or an ester bond.
- R 4 includes an aryl group or heterocyclic group having 6 to 40 carbon atoms which may be substituted with a halogen group, a nitro group, an amino group or a hydroxy group. It is done.
- R 5 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group, Examples thereof include aryl groups and heterocyclic groups having 6 to 40 carbon atoms.
- R 4 and R 5 may be combined with the carbon atom to which they are bonded to form a ring.
- R 4 and R 5 are fluorene rings formed together with the carbon atom to which they are bonded, and the carbon atom is a fluorene which is the carbon atom at the 9-position of the formed fluorene ring. Examples thereof include a ring structure.
- n1 and n2 are each an integer of 1 to 3
- n3 to n5 are integers of 1 to 4, respectively.
- halogen group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
- alkyl group having 1 to 10 carbon atoms examples include methyl group, ethyl group, n-propyl group, i-propyl group, cyclopropyl group, n-butyl group, i-butyl group, s-butyl group, t- Butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n -Butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, cyclopentyl group, 1 -Methyl-cyclobutyl group, 2-methyl-cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,3
- alkenyl group having 2 to 10 carbon atoms examples include ethenyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-ethenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group 3-pentenyl group, 4-pentenyl group, 1-n-propylethenyl group, 1-methyl-1-butenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-ethyl -2-propenyl group, 2-methyl-1-butenyl group, 2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-1-butenyl group, 3-methyl-2-butenyl group 3-methyl-3methyl
- Examples of the aryl group having 6 to 40 carbon atoms include phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl group, and p-chlorophenyl.
- o-fluorophenyl group p-fluorophenyl group, o-methoxyphenyl group, p-methoxyphenyl group, p-nitrophenyl group, p-cyanophenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, o- Biphenyl, m-biphenyl, p-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9- A phenanthryl group may be mentioned.
- the heterocyclic group is preferably an organic group composed of a 5- or 6-membered heterocyclic ring containing nitrogen, sulfur or oxygen, such as a pyrrole group, a furan group, a thiophene group, an imidazole group, an oxazole group, a thiazole group, or a pyrazole.
- a pyrrole group a furan group
- a thiophene group an imidazole group
- an oxazole group a thiazole group
- pyrazole a 5- or 6-membered heterocyclic ring containing nitrogen, sulfur or oxygen
- Examples of the polymer containing a unit structure preferable as the above formula (1) can be exemplified below.
- the polymer represented by the formula (1) of the present invention is obtained by condensing carbazoles with aldehydes or ketones.
- aldehydes or ketones can be used at a ratio of 0.1 to 10 equivalents with respect to 1 equivalent of the phenyl group of the carbazoles.
- the polymers represented by the formulas (2) and (3) of the present invention are obtained by condensing carbazoles, triphenylamines and aldehydes or ketones.
- carbazoles and triphenylamines can be used in a molar ratio of 1: 0.01 to 1: 100.
- An aldehyde or a ketone can be used at a ratio of 0.1 to 10 equivalents with respect to 1 equivalent of a phenyl group in which carbazoles and triphenylamines are combined.
- carbazoles used in the production of the polymer of the present invention include carbazole, N-methylcarbazole, N-ethylcarbazole, 1,3,6,8-tetranitrocarbazole, 3,6-diaminocarbazole, and 3,6-dibromo.
- aldehydes used for producing the polymer of the present invention include formaldehyde, paraformaldehyde, acetaldehyde, propyl aldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, capronaldehyde, 2-methylbutyraldehyde, hexyl aldehyde, undecane aldehyde, 7 -Saturated aliphatic aldehydes such as methoxy-3,7-dimethyloctylaldehyde, cyclohexanealdehyde, 3-methyl-2-butyraldehyde, glyoxal, malonaldehyde, succinaldehyde, glutaraldehyde, glutaraldehyde, adipine aldehyde, thiophene aldehyde , Unsaturated aliphatic aldehydes such as acrolein
- the ketones used in the production of the polymer of the present invention are not particularly limited.
- diaryl ketones such as diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone.
- diaryl ketones such as diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone.
- examples of the triphenylamines used in the production of the polymer of the present invention include triphenylamine and substituted triphenylamine.
- Examples of the substituent of triphenylamine include the above-mentioned halogen group, nitro group, amino group, hydroxy group, alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, and 6 to 40 carbon atoms.
- the alkyl group, the alkenyl group or the aryl group is selected from the group consisting of an aryl group and a combination thereof, and examples of the alkyl group, the alkenyl group or the aryl group include an ether bond, a ketone bond or an ester bond.
- Examples of the acid catalyst used in the above condensation reaction include mineral acids such as sulfuric acid, phosphoric acid and perchloric acid, organic sulfonic acids such as p-toluenesulfonic acid and p-toluenesulfonic acid monohydrate, formic acid and oxalic acid. And carboxylic acids such as The usage-amount of an acid catalyst is suitably selected according to the kind of acid to be used. Usually, 0.001 to 10000 parts by mass, preferably 0.01 to 1000 parts by mass, more preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of carbazoles or the total of carbazoles and triphenylamines. Part by mass.
- the above condensation reaction is usually carried out in a solvent, but can also be carried out without using a solvent.
- Any solvent can be used as long as it does not inhibit the condensation reaction. Examples thereof include cyclic ethers such as tetrahydrofuran and dioxane.
- the acid catalyst used is a liquid such as formic acid, it can also serve as a solvent.
- the reaction temperature during the condensation is usually 40 ° C to 200 ° C.
- the reaction time is variously selected depending on the reaction temperature, but is usually about 30 minutes to 50 hours.
- the weight average molecular weight Mw of the polymer composed of the unit structure represented by the formula (1) or (2) and / or (3) synthesized by the above method is usually 600 to 1000000, or 600 to 200000. .
- the above polymer can be used by mixing other polymers in the whole polymer within 30% by mass.
- polymers that can be mixed include polyacrylic acid ester compounds, polymethacrylic acid ester compounds, polyacrylamide compounds, polymethacrylamide compounds, polyvinyl compounds, polystyrene compounds, polymaleimide compounds, polymaleic anhydrides, and polyacrylonitrile compounds. Can be mentioned.
- Raw material monomers for the polyacrylic acid ester compounds include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate 2,2,2-trifluoroethyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl Acrylate, tetrahydrofurfuryl acrylate, 3-methoxybutyl acetate 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, 2-propyl-2
- Examples of the raw material monomer for the polymethacrylate compound include ethyl methacrylate, normal propyl methacrylate, normal pentyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, 2-phenylethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trichloroethyl methacrylate, methyl acrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, normal lauryl Methacrylate, normal stearyl methacrylate Rate, methoxydiethylene glycol methacrylate, methoxypolyethylene glycol methacrylate
- acrylamide compound examples include acrylamide, N-methyl acrylamide, N-ethyl acrylamide, N-benzyl acrylamide, N-phenyl acrylamide, and N, N-dimethyl acrylamide.
- Examples of the raw material monomer of the polymethacrylic acid amide compound include methacrylamide, N-methyl methacrylamide, N-ethyl methacrylamide, N-benzyl methacrylamide, N-phenyl methacrylamide, N, N-dimethyl methacrylamide and the like. It is done.
- Examples of the raw material monomer for the polyvinyl compound include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.
- Examples of the raw material monomer of the polystyrene compound include styrene, methylstyrene, chlorostyrene, bromostyrene, and hydroxystyrene.
- Examples of the raw material monomer for the polymaleimide compound include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
- These polymers are prepared by dissolving an addition polymerizable monomer and, if necessary, a chain transfer agent in an organic solvent, adding a polymerization initiator to perform a polymerization reaction, and then adding a polymerization terminator to stop the polymerization reaction. Can be manufactured.
- the addition amount of the chain transfer agent is, for example, 10% or less with respect to the mass of the monomer
- the addition amount of the polymerization initiator is, for example, 1 to 10% with respect to the mass of the monomer.
- the added amount of is, for example, 0.01 to 0.2% by mass with respect to the mass of the monomer.
- Examples of the organic solvent include propylene glycol monomethyl ether, propylene glycol monopropyl ether, ethyl lactate, cyclohexanone, methyl ethyl ketone, and dimethylformamide.
- Examples of the chain transfer agent include dodecanethiol and dodecylthiol.
- Examples of the polymerization initiator include azobisisobutyronitrile and azobiscyclohexanecarbonitrile.
- Examples of the polymerization terminator include 4-methoxyphenol.
- the reaction temperature for the polymerization reaction is appropriately selected from 30 to 100 ° C., and the reaction time is appropriately selected from 1 to 48 hours.
- the present invention relates to a resist underlayer film forming composition containing a polymer containing a unit structure represented by the above formula (1) or a polymer containing a unit structure represented by the formula (2) and / or the formula (3).
- the resist underlayer film forming composition contains the polymer and a solvent. Furthermore, additives, such as a crosslinking agent and an acid, and an acid generator and surfactant, can be included as needed.
- the ratio of the solid content in this composition is 0.1 to 70% by mass, or 0.1 to 60% by mass with respect to the total mass of the composition.
- Solid content means the component remove
- the polymer can be contained in the solid content in a proportion of 1 to 100% by mass, or 1 to 99.9% by mass, or 50 to 99.9% by mass.
- the crosslinking agent examples include melamine type, substituted urea type, or polymer type thereof.
- it is a cross-linking agent having at least two cross-linking substituents, such as methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzogwanamine, butoxymethylated Compounds such as benzoguanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or methoxymethylated thiourea.
- the condensate of these compounds can also be used.
- a crosslinking agent having high heat resistance can be used as the crosslinking agent.
- a compound containing a crosslinking-forming substituent having an aromatic ring such as a benzene ring and a naphthalene ring in the molecule can be preferably used as the crosslinking agent having high heat resistance.
- this compound include a compound having a partial structure of the following formula (4) and a polymer or oligomer having a unit structure of the following formula (5).
- R 9 and R 10 each represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms
- n6 is an integer of 1 to 4
- n7 Is an integer from 1 to (5-n6)
- (n9 + n10) is an integer from 2 to 5.
- R 11 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- R 12 represents an alkyl group having 1 to 10 carbon atoms
- n11 is an integer of 1 to 4
- (n11 + n12) is an integer of 1 to 4.
- the polymer or oligomer having a unit structure of the formula (5) preferably has a repeating number of 2 to 100, or 2 to 50.
- Examples of the alkyl group and aryl group representing R 9 to R 11 include the alkyl groups and aryl groups described above.
- the above compounds can be obtained as products of Asahi Organic Materials Industry Co., Ltd. and Honshu Chemical Industry Co., Ltd.
- the compound of the formula (4-21) can be obtained as Asahi Organic Materials Co., Ltd., trade name TM-BIP-A.
- the blending amount of the crosslinking agent in the resist underlayer film forming composition of the present invention is required for the coating solvent for the composition, the base substrate on which the composition is applied, the solution viscosity required for the composition, and the film formed from the composition. It is determined appropriately depending on the film shape. For example, the content is 0.001 to 80% by mass, preferably 0.01 to 50% by mass, and more preferably 0.05 to 40% by mass with respect to the total solid content.
- These crosslinking agents may cause a crosslinking reaction due to self-condensation, but when a crosslinking substituent is present in the above-described polymer of the present invention, it can cause a crosslinking reaction with these crosslinking substituents.
- the resist underlayer film forming composition of the present invention may contain an acid, a thermal acid generator or a photoacid generator as a catalyst for promoting the crosslinking reaction.
- the heat generating agent is a compound that generates an acid upon heating.
- acidic compounds such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid, and / or 2
- thermal acid generators that generate acids such as 4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters.
- the amount of the thermal acid generator is 0.0001 to 20% by mass, preferably 0.0005 to 10% by mass, preferably 0.01 to 3% by mass, based on the total solid content of the resist underlayer film forming composition. %.
- a photoacid generator can be added in order to match the acidity with the resist coated on the upper layer of the resist underlayer film formed therefrom in the lithography process.
- Preferred photoacid generators include, for example, onium salt photoacid generators such as bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s.
- onium salt photoacid generators such as bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s.
- -Halogen-containing compound photoacid generators such as triazine
- sulfonic acid photoacid generators such as benzoin tosylate and N-hydroxysuccinimide trifluoromethanesulfonate.
- the blending amount of the photoacid generator is 0.2 to 10% by mass, preferably 0.4 to 5% by mass, based on the total solid content of the resist underlayer film forming composition.
- a light absorber a rheology modifier, an adhesion aid, a surfactant, and the like can be further added to the resist underlayer film forming composition of the present invention as necessary.
- Examples of the light absorbing agent include commercially available light absorbing agents described in “Technical dye technology and market” (published by CMC) or “Dye Handbook” (edited by the Society of Synthetic Organic Chemistry), for example, C.I. I. Disperse Yellow 1, 3, 4, 5, 7, 8, 13, 23, 31, 49, 50, 51, 54, 60, 64, 66, 68, 79, 82, 88, 90, 93, 102, 114 and 124; C.I. I. D isprange Orange 1, 5, 13, 25, 29, 30, 31, 44, 57, 72 and 73; I. Disperse Red 1, 5, 7, 13, 17, 19, 43, 50, 54, 58, 65, 72, 73, 88, 117, 137, 143, 199 and 210; I.
- the above light-absorbing agent is usually blended at a ratio of 10% by mass or less, preferably 5% by mass or less based on the total solid content of the resist underlayer film forming composition.
- the rheology modifier mainly improves the fluidity of the resist underlayer film forming composition, and in particular, in the baking process, improves the film thickness uniformity of the resist underlayer film, or the resist underlayer film forming composition inside the hole of the substrate. It is added for the purpose of improving the filling property.
- rheology modifier examples include phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate; , Maleic acid derivatives such as dinormal butyl maleate, diethyl maleate and dinonyl maleate, oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate, or stearic acid derivatives such as normal butyl stearate and glyceryl stearate It is done. These rheology modifiers are usually blended at a ratio of less than 30% by mass with respect to the total solid content of the resist underlayer film forming composition.
- the above-mentioned adhesion auxiliary agent is added mainly for the purpose of improving the adhesion between the substrate or resist and the resist underlayer film forming composition and preventing the resist from peeling particularly in the development process.
- Specific examples include chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, chloromethyldimethylchlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, Alkoxysilanes such as enyltriethoxysilane, hexamethyldisilazane, N, N'-bis (trimethylsilyl) urea, silazanes such as dimethyltrimethylsilylamine, trimethylsilylimidazole, vinyltrichlorosilane, ⁇ -chlor
- adhesion assistants are usually blended in a proportion of less than 5% by mass, preferably less than 2% by mass, based on the total solid content of the resist underlayer film forming composition.
- a surfactant can be blended in order to suppress the occurrence of pinholes and installations and to further improve the applicability to surface unevenness of the substrate and the like.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octyl phenol ether, polyoxyethylene Polyoxyethylene alkyl allyl ethers such as nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan trioleate Sorbitan fatty acid esters such as stearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as poly
- the blending amount of these surfactants is usually 2.0% by mass or less, preferably 1.0% by mass or less, based on the total solid content of the resist underlayer film forming composition of the present invention.
- These surfactants can be added alone or in combination of two or more.
- additives such as the polymer, the crosslinking agent component, and the crosslinking catalyst may be added after being dissolved in a solvent.
- solvent for dissolving the additive include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate, ethylene glycol ethyl ether acetate, methyl cellosolve acetate, Ethyl cellosolve acetate, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monoethyl ether acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monobutyl ether Propylene glycol monomethyl ether acetate, propylene glycol monoethyl acetate, propy
- propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, cyclohexanone, or the like is preferable for improving the leveling property.
- ⁇ Resist underlayer film> From the resist underlayer film forming composition of the present invention, a resist underlayer film used in a lithography process in the production of a semiconductor device can be formed.
- the resist underlayer film of the present invention is formed on a substrate (for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, or an ITO substrate) used for manufacturing a precision integrated circuit element by an appropriate coating method such as a spinner or a coater.
- a substrate for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, or an ITO substrate
- an appropriate coating method such as a spinner or a coater.
- the resist underlayer film forming composition of the invention is applied, baked and cured.
- the film thickness of the resist underlayer film formed on the substrate can be adjusted as appropriate, but is preferably 0.01 to 3.0 ⁇ m, for example. Further, the baking conditions after the application of the resist underlayer film may be as long as the performance as the resist underlayer film is not impaired.
- the resist underlayer film of the present invention has a dry etching rate selectivity close to that of the resist or smaller than that of the resist or the substrate, unlike the conventional resist underlayer film having a high etch rate.
- the resist underlayer film of the present invention contains a light absorption site having sufficiently large light absorption performance such as a carbazole skeleton, a benzene ring and a fluorene ring in the polymer.
- a light absorption site having sufficiently large light absorption performance such as a carbazole skeleton, a benzene ring and a fluorene ring in the polymer.
- it has a performance as an antireflection film that absorbs reflection of light or electron beam from the substrate.
- a light absorber to the resist film or the like is present when the resist is heated and dried. It also has the effect that it does not diffuse.
- the resist underlayer film of the present invention has higher thermal stability than the conventional resist underlayer film because the polymer contains a carbazole skeleton, a benzene ring, a fluorene ring, and the like.
- production of the decomposition product at the time of baking can be suppressed, and it is hard to raise
- the resist underlayer film of the present invention is a preventive film having a function of preventing the interaction between the substrate and the resist, or a function of preventing the adverse effect on the substrate of a resist forming composition or a substance generated upon exposure to the resist. Can be used.
- a fine resist pattern can be formed by using the resist film of the present invention.
- the resist pattern forming method of the present invention will be described.
- a resist underlayer film is formed on a substrate as described above.
- the resist-forming composition is applied and cured directly on the resist underlayer film or, if necessary, on a film obtained by applying and curing one to several layers of coating material on the resist underlayer film.
- a good resist pattern can be obtained by irradiating with light or an electron beam through a predetermined mask in which a pattern is drawn on the formed resist, developing, rinsing, and drying. If necessary, post-irradiation heating (PEB: Post Exposure Bake) may be performed.
- PEB Post Exposure Bake
- the resist used in the present invention is a photoresist or an electron beam resist.
- a negative type or a positive type can be used.
- a positive type photoresist composed of a novolak resin and 1,2-naphthoquinonediazide sulfonate, Chemically amplified photoresist comprising a binder having a group that decomposes to increase the alkali dissolution rate and a photoacid generator, a low molecular weight compound and photoacid that increases the alkali dissolution rate of the photoresist by decomposition with an alkali-soluble binder and acid Chemically amplified photoresist comprising a generator, comprising a binder having a group that decomposes with acid to increase the alkali dissolution rate, a low-molecular compound that decomposes with acid to increase the alkali dissolution rate of the photoresist,
- the electron beam resist applied to the upper part of the resist underlayer film in the present invention includes, for example, a resin that contains a Si—Si bond in the main chain and an aromatic ring at the terminal, and an acid generator that generates an acid upon irradiation with an electron beam.
- a composition comprising a poly (p-hydroxystyrene) having a hydroxy group substituted with an organic group containing N-carboxyamine and an acid generator that generates an acid upon irradiation with an electron beam.
- the acid generated from the acid generator by electron beam irradiation reacts with the N-carboxyaminoxy group of the polymer side chain, and the polymer side chain decomposes to form a hydroxy group. Therefore, the polymer becomes alkali-soluble. Therefore, the portion irradiated with the electron beam is dissolved in the alkaline developer to form a resist pattern.
- Examples of acid generators that generate an acid upon irradiation with this electron beam include 1,1-bis [p-chlorophenyl] -2,2,2-trichloroethane, 1,1-bis [p-methoxyphenyl] -2,2, Halogenated organic compounds such as 2-trichloroethane, 1,1-bis [p-chlorophenyl] -2,2-dichloroethane, 2-chloro-6- (trichloromethyl) pyridine, triphenylsulfonium salts, diphenyliodonium salts, etc. And sulfonic acid esters such as nitrobenzyl tosylate and dinitrobenzyl tosylate.
- inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine Secondary amines such as diethylamine and di-n-butylamine, tertiary amines such as triethylamine and methyldiethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, tetramethylammonium hydroxide, An aqueous solution of alkalis such as quaternary ammonium salts such as tetraethylammonium hydroxide and choline, cyclic amines such as pyrrole and piperidine, and the like can be used.
- quaternary ammonium salts such as tetraethylammonium hydroxide and choline
- cyclic amines such as pyrrole and piperidine, and the like
- an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
- the exposure light for the photoresist is actinic radiation such as near ultraviolet, far ultraviolet, or extreme ultraviolet (for example, EUV, wavelength 13.5 nm), for example, 248 nm (KrF laser light), 193 nm (ArF laser light).
- Light having a wavelength such as 157 nm (F 2 laser light) is used.
- the light irradiation can be used without particular limitation as long as it can generate an acid from a photoacid generator.
- the exposure amount is 1 to 2000 mJ / cm 2 , or 10 to 1500 mJ / cm 2 , Or 50 to 1000 mJ / cm 2 .
- the electron beam irradiation in the electron beam resist process can be performed using, for example, an electron beam irradiation device.
- the resist underlayer film of the present invention does not cause intermixing with the resist forming composition, and has an effect as a planarizing film and an antireflection film. Therefore, a fine resist pattern that does not cause pattern collapse or the like can be obtained from the resist formed on the resist underlayer film of the present invention.
- the resist underlayer film of the present invention has a dry etching rate selection ratio close to that of the resist. A thinner method can be used, and a fine resist pattern can be obtained.
- a semiconductor device includes a step of forming a resist underlayer film on a semiconductor substrate with a resist underlayer film forming composition, a step of forming a resist film on the resist underlayer film, and light or electrons using a mask on which a pattern is drawn. Forming a resist pattern on the resist film by irradiating and developing a line, etching the resist underlayer film in accordance with the resist pattern, and processing the semiconductor substrate using the patterned resist underlayer film It can be manufactured after that.
- resist thinning has been performed in order to prevent the resist pattern from collapsing after development as the resist pattern becomes finer.
- a resist pattern is transferred to the lower layer film by an etching process, and a substrate is processed using the lower layer film, or the resist pattern is applied to the lower layer film by an etching process.
- the substrate is finally processed by repeating the process of transferring and transferring the pattern transferred to the lower layer film to the lower layer film by an etching process using a different gas composition.
- films having various functions can be formed between the resist film and the resist underlayer film. Therefore, even if the resist film is thinly formed for the purpose of obtaining a fine pattern, the substrate can be easily processed without falling down by selecting an appropriate etching gas.
- the film formed on the resist underlayer film examples include a coating film obtained by applying and curing a coating material containing an organic polymer or an inorganic polymer and a solvent, or a hard mask on which an inorganic substance such as silicon nitride oxide is deposited. . Since the resist underlayer film of the present invention has heat resistance, an inorganic substance can be deposited on the resist underlayer film.
- the gas used in the above etching process may be one used in a conventional process, and is appropriately selected depending on the layer or substrate to be etched.
- hydrogen-based, oxygen-based, and halogen-based gases can be used.
- the semiconductor device of the present invention includes a step of forming a resist underlayer film on a semiconductor substrate with the resist underlayer film forming composition of the present invention, a step of forming a resist film on the resist underlayer film, and a mask on which a pattern is drawn.
- the semiconductor device of the present invention comprises a step of forming a resist underlayer film on a semiconductor substrate with the resist underlayer film forming composition of the present invention, a hard mask made of a coating material containing a silicon component or the like on the resist underlayer film, or A step of forming a hard mask (for example, silicon nitride oxide) by vapor deposition, a step of forming a resist film on the hard mask, irradiation of light or electron beam using a mask on which a pattern is drawn and development and development Forming a resist pattern on the substrate, etching the hard mask with a halogen-based gas according to the resist pattern, etching the resist underlayer film with an oxygen-based gas or a hydrogen-based gas according to the patterned hard mask, and patterning Of processing a semiconductor substrate with a halogen-based gas using the resist underlayer film formed It can be produced through.
- a hard mask for example, silicon nitride oxide
- the present invention is a carbazole ring that can achieve high heat resistance, high transparency, high refractive index, and high solubility independently without using a metal oxide as an application different from the resist underlayer film, or
- a high refractive index film including a polymer containing a carbazole ring and a triphenylamine ring can be provided.
- the present invention provides at least one selected from the group consisting of a unit structure represented by the above formula (1), a unit structure represented by the above formula (2), and a unit structure represented by the above formula (3).
- the present invention relates to a high refractive index film-forming composition containing a polymer containing a seed unit structure, that is, a carbazole novolak resin, a high refractive index film formed therefrom, and an electronic device including the high refractive index film. This will be described below.
- the high refractive index film-forming composition contains the polymer and a solvent.
- other components such as the above-mentioned crosslinking agent, acid generator, surfactant, leveling agent and the like may be contained within a range not impairing the effect as a high refractive index film.
- the solid content concentration of the high refractive index film-forming composition is not particularly limited as long as it does not affect the storage stability, and may be appropriately set according to the target film thickness. From the viewpoint of solubility and storage stability, the solid content concentration is preferably 0.1 to 50% by mass, and more preferably 0.1 to 20% by mass.
- the solvent include the above solvents.
- the polymer can be contained in the solid content in a proportion of 1 to 100% by mass, or 1 to 99.9% by mass, or 50 to 99.9% by mass.
- the polymer contained in the high refractive index film-forming composition of the present invention is, for example, a highly branched polymer or a linear polymer having a weight average molecular weight of 1,000 to 2,000,000.
- the polymer of the present invention is a high molecular weight compound, it has a low viscosity when dissolved in a solvent, and therefore has excellent handling properties.
- the high refractive index film-forming composition includes a thermoplastic resin containing another polymer in addition to the polymer containing the unit structure represented by the above formulas (1), (2) and (3), or the heat thereof.
- a plastic resin composition may be included.
- polystyrene resin examples include polyethylene resin, polypropylene resin, polystyrene resin, acrylonitrile / butadiene / styrene resin (ABS), polycarbonate resin, polyethylene terephthalate resin, polyamide resin, polyimide resin, (meth) Acrylic resin, polyester resin (including polyethylene terephthalate), polynorbornene resin, polylactic acid resin, polyurethane resin, polyether resin, polyethersulfone resin, polyetherketone resin, polythioether resin, phenolic resin, urea resin, melamine resin, Examples thereof include unsaturated polyester resins and epoxy resins.
- the resin is preferably used in the range of 1 to 10,000 parts by mass, more preferably in the range of 1 to 1,000 parts by mass with respect to 100 parts by mass of the polymer.
- composition with a (meth) acrylic resin it can be obtained by mixing the (meth) acrylate compound and the polymer and polymerizing the (meth) acrylate compound.
- Examples of the (meth) acrylate compound include methyl (meth) acrylate, ethyl (meth) acrylate, ethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol Di (meth) acrylate, polypropylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane Trioxyethyl (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, tricyclodecanyl di (meth) acrylate, trimethylolpropane trioxypropyl ( ) Acrylate, tris-2-hydroxyethyl isocyanurate tri (meth
- Polymerization of these (meth) acrylate compounds can be carried out by light irradiation or heating in the presence of a photo radical initiator or a heat radical initiator.
- photo radical polymerization initiators include acetophenones, benzophenones, Michler's benzoylbenzoate, amyloxime ester, tetramethylthiuram monosulfide, and thioxanthones.
- a photocleavable photo radical polymerization initiator is preferred.
- the photocleavable photoradical polymerization initiator is described in the latest UV curing technology (p. 159, publisher: Kazuhiro Takahisa, publisher: Technical Information Association, Inc., published in 1991).
- photo radical polymerization initiators examples include, for example, trade names: Irgacure 184, 369, 651, 500, 819, 907, 784, 2959, CGI 1700, CGI 1750, CGI 1850, CG24-61, Darocur, manufactured by Ciba Japan Co., Ltd. 1116, 1173, manufactured by BASF, Inc.
- Product name Ubekrill P36, manufactured by Fratteri Lamberti, Inc.
- the photopolymerization initiator is preferably used in the range of 0.1 to 15 parts by mass, more preferably in the range of 1 to 10 parts by mass with respect to 100 parts by mass of the (meth) acrylate compound.
- the solvents described in the film forming composition can be used.
- a high refractive index film can be obtained by applying the high refractive index forming composition of the present invention to a substrate or the like and curing it.
- the high refractive index film of the present invention includes a carbazole ring or a polymer containing a carbazole ring and a triphenylamine ring and containing a novolac-based unit structure. Therefore, the high refractive index film has extremely high heat resistance. Does not occur. Furthermore, the high refractive index film of the present invention can maintain high heat resistance and high transparency, and even when using a monomer unit that has been thought to impair heat resistance and transparency, There is a possibility that physical properties can be controlled only by changing to the partial structure of the invention. That is, the physical properties of the high refractive index film of the present invention can be controlled by changing the type of monomer that is a starting material at the time of synthesis of the contained polymer. For example, the carbazole ring-containing polymer of the present invention, or the carbazole ring and triphenylamine ring-containing polymer can be used as a high heat-resistant insulating material.
- the high refractive index film of the present invention does not contain a metal oxide and can express a high refractive index with a polymer alone, even when a dry process such as etching or ashing is performed, the etching rate is constant and the film thickness is uniform. Thus, the process margin when manufacturing the device is expanded.
- the high refractive index film of the present invention having such characteristics as high heat resistance, high transparency, high refractive index, high solubility, and low volume shrinkage is a liquid crystal display, an organic electroluminescence (EL) display, light It can be suitably used as an optical member for producing electronic devices such as semiconductor (LED) elements, solid-state imaging elements, organic thin film solar cells, dye-sensitized solar cells, and organic thin film transistors (TFTs).
- LED semiconductor
- solid-state imaging elements organic thin film solar cells
- dye-sensitized solar cells dye-sensitized solar cells
- TFTs organic thin film transistors
- 1,4-dioxane (15 g, manufactured by Kanto Chemical Co., Inc.) was added, the temperature was raised to 100 ° C. with stirring, and a polymerization reaction was carried out for 1.5 hours. After completion of the reaction, the reaction mixture was allowed to cool to 30 ° C., diluted by adding chloroform (60 g, manufactured by Kanto Chemical Co., Inc.), and precipitated by adding this solution to methanol (300 g, manufactured by Kanto Chemical Co., Inc.). The obtained precipitate was filtered, dried in a vacuum dryer at 60 ° C. for 10 hours, and further dried at 120 ° C. for 24 hours to obtain a target polymer (mixture of formula (2-1) and formula (3-1)).
- PTPABACz (Hereinafter abbreviated as PTPABACz) to obtain 11.74 g.
- the measurement result of the 1 H-NMR spectrum of PTPABACz is shown in FIG.
- the results of 1 H-NMR measurement of PTPABACz were as follows. 1 H-NMR (300 MHz, DMSO-d 6 ): ⁇ 4.74-6.36 (br, 1.2H), ⁇ 6.38-7.54 (br, 12H), ⁇ 7.57-8.31 (br , 2H), ⁇ 10.48-11.50 (br, 1H)
- the weight average molecular weight Mw measured by GPC of PTPABACz in terms of polystyrene was 6400, and the polydispersity Mw / Mn was 1.93.
- the 1 H NMR spectrum of the obtained PCzNA is shown in FIG. Moreover, the weight average molecular weight Mw measured by polystyrene conversion by GPC of PCzNA was 2,100, and the polydispersity Mw / Mn was 1.34.
- 1,4-dioxane (3.0 g, manufactured by Kanto Chemical Co., Inc.) was added, the temperature was raised to 100 ° C. with stirring, and a polymerization reaction was carried out for 7 hours. After completion of the reaction, the mixture was allowed to cool to 60 ° C., diluted by adding chloroform (10 g, manufactured by Kanto Chemical Co., Inc.), and reprecipitated by adding this solution to methanol (100 g, manufactured by Kanto Chemical Co., Inc.). The resulting precipitate was filtered and dried at 60 ° C. for 10 hours in a vacuum dryer to obtain 4.13 g of the target polymer (formula (1-6), hereinafter abbreviated as PCzAA).
- PCzAA the target polymer
- the 1 H NMR spectrum of the obtained PCzAA is shown in FIG. Moreover, the weight average molecular weight Mw measured by polystyrene conversion by GPC of PCzAA was 2,100, and polydispersity Mw / Mn was 1.77.
- the reaction mixture was allowed to cool to 60 ° C., diluted by adding chloroform (25 g, manufactured by Kanto Chemical Co., Inc.), and reprecipitated by adding this solution to methanol (125 g, manufactured by Kanto Chemical Co., Inc.).
- the resulting precipitate was filtered, redissolved in chloroform (25 g), and added to methanol (125 g, manufactured by Kanto Chemical Co., Inc.) for reprecipitation.
- the obtained precipitate was filtered and dried with a vacuum dryer at 60 ° C. for 10 hours to obtain 7.75 g of a target polymer (formula (1-7), hereinafter abbreviated as PCzPBA).
- the 1 H NMR spectrum of the obtained PCzPBA is shown in FIG. Moreover, the weight average molecular weight Mw measured by polystyrene conversion by GPC of PCzPBA was 3,800, and polydispersity Mw / Mn was 1.52.
- the 1 H NMR spectrum of the obtained PCzTPA is shown in FIG. Moreover, the weight average molecular weight Mw measured by polystyrene conversion by GPC of PCzTPA was 6,300, and polydispersity Mw / Mn was 2.50.
- ⁇ Synthesis Example 12> In a 100 mL four-necked flask under a nitrogen atmosphere, 9-ethylcarbazole (3.0 g, 15.4 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), benzaldehyde (1.65 g, 15.5 mmol, manufactured by Junsei Chemical Co., Ltd.), and Paratoluenesulfonic acid monohydrate (0.29 g, 1.54 mmol, manufactured by Kanto Chemical Co., Inc.) was added. Further, 1,4-dioxane (3.0 g, manufactured by Kanto Chemical Co., Inc.) was added, the temperature was raised to 110 ° C.
- PEtCzBA a target polymer (formula (1-12), hereinafter abbreviated as PEtCzBA).
- the 1 H NMR spectrum of the obtained PEtCzBA is shown in FIG.
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of PEtCzBA was 1,200
- polydispersity Mw / Mn was 1.27.
- the mixture was allowed to cool to 60 ° C., diluted with THF (10 g, manufactured by Kanto Chemical Co., Inc.), and precipitated into methanol (100 g, manufactured by Kanto Chemical Co., Inc.).
- the obtained precipitate was filtered, redissolved in THF (10 g, manufactured by Kanto Chemical Co., Inc.), and mixed with methanol (60 g, manufactured by Kanto Chemical Co., Ltd.) and THF (30 g, manufactured by Kanto Chemical Co., Ltd.). It was added to the solvent and reprecipitated.
- the obtained precipitate was filtered again and dried in a vacuum dryer at 60 ° C.
- PEtCzNA target polymer
- the 1 H NMR spectrum of the obtained PEtCzNA is shown in FIG.
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of PEtCzNA was 1,000, and polydispersity Mw / Mn was 1.29.
- FIG. 15 shows the 1 H NMR spectrum of the obtained PPBA.
- the weight average molecular weight Mw measured by polystyrene conversion by PPBA GPC was 23,000, and polydispersity Mw / Mn was 6.24.
- Example 1 0.06 g of Megafac R-30 (Dainippon Ink Chemical Co., Ltd., trade name) as a surfactant is mixed with 20 g of PCzBA synthesized in Synthesis Example 1, and dissolved in 80 g of propylene glycol monomethyl ether acetate. The solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to form a resist underlayer film forming composition for use in a lithography process using a multilayer film. A solution of was prepared.
- Example 2 20 g of PCzBA synthesized in Synthesis Example 1, 2.0 g of TM-BIP-A (manufactured by Asahi Organic Materials Co., Ltd., trade name) as a cross-linking agent, 0.10 g of pyridinium p-toluenesulfonate as a catalyst, and megafac as a surfactant 0.06 g of R-30 (Dainippon Ink Chemical Co., Ltd., trade name) was mixed and dissolved in 88 g of propylene glycol monomethyl ether acetate.
- TM-BIP-A manufactured by Asahi Organic Materials Co., Ltd., trade name
- R-30 Dainippon Ink Chemical Co., Ltd., trade name
- This solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to form a resist underlayer film forming composition for use in a lithography process using a multilayer film
- a solution of was prepared.
- Example 3 To 20 g of PCzNA obtained in Synthesis Example 2, 0.06 g of Megafac R-30 (manufactured by Dainippon Ink & Chemicals, Inc.) as a surfactant was mixed and dissolved in 80 g of propylene glycol monomethyl ether acetate. The solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to form a resist underlayer film forming composition for use in a lithography process using a multilayer film. A solution of was prepared.
- Megafac R-30 manufactured by Dainippon Ink & Chemicals, Inc.
- Example 4 To the PTPABACz 20 g obtained in Synthesis Example 3, 0.06 g of Megafac R-30 (Dainippon Ink Chemical Co., Ltd., trade name) was mixed as a surfactant and dissolved in 80 g of propylene glycol monomethyl ether acetate. This solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to form a resist underlayer film forming composition for use in a lithography process using a multilayer film A solution of was prepared.
- Megafac R-30 Dainippon Ink Chemical Co., Ltd., trade name
- Example 5 0.06 g of Megafac R-30 (Dainippon Ink Chemical Co., Ltd., trade name) as a surfactant was mixed with 20 g of PCzFL obtained in Synthesis Example 4, and dissolved in 80 g of propylene glycol monomethyl ether acetate. This solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to form a resist underlayer film forming composition for use in a lithography process using a multilayer film A solution of was prepared.
- Megafac R-30 Dainippon Ink Chemical Co., Ltd., trade name
- This solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to form a resist underlayer film forming composition for use in a lithography process using a multilayer film
- a solution of was prepared.
- the resist underlayer film forming composition solutions prepared in Examples 1 to 6 and Comparative Example 1 were applied onto a silicon wafer using a spin coater, and baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes. Then, a resist underlayer film (film thickness 0.25 ⁇ m) was formed. Similarly, a phenol-novolak resin (commercial product, weight average molecular weight Mw measured in terms of polystyrene by GPC is 2000, polydispersity Mw / Mn is 2.5) is applied onto a silicon wafer using a spin coater. It was applied and baked at 205 ° C. for 1 minute to form a coating film.
- a phenol-novolak resin commercial product, weight average molecular weight Mw measured in terms of polystyrene by GPC is 2000, polydispersity Mw / Mn is 2.5
- the etching rate of the formed resist underlayer film was measured.
- the dry etching rate was measured using CF 4 gas as the etching gas.
- the dry etching rate of the resist underlayer films of Examples 1 to 6 and Comparative Example 1 when the etching rate of the phenol novolak resin film (film thickness: 0.25 ⁇ m) obtained by baking at 205 ° C. for 1 minute was 1.00 A comparison was made. The results are shown in Table 2.
- the dry etching rate ratio was obtained from (Dry etching rate of resist underlayer film) / (Dry etching rate of phenol novolac resin film).
- thermophysical properties of polymers For each of the polymers obtained in Synthesis Examples 5 to 13 and Comparative Synthesis Example 1 or 2, 5% weight loss temperature (Td 5% ) and glass transition temperature (Tg) were measured. The results are shown in Table 4.
- the carbazole novolak resin of the present invention has a very high heat resistance because it exhibits a higher temperature than the novolak resin having no carbazole skeleton with respect to the 5% weight loss temperature and the glass transition temperature. I understand that.
- the high refractive index film of the present invention has a refractive index of 1.72 to 1.80 at a wavelength of 550 nm and a refractive index of 1.70 to 1.77 at a wavelength of 633 nm. It was found that the refractive index was high. Further, from the light transmission spectra shown in FIGS. 16 to 26, it can be seen that the carbazole novolak resin of the present invention has high transparency particularly in the visible light region.
- the resist underlayer film forming composition used in the lithography process of the present invention forms a resist underlayer film having a dry etching rate selectivity close to or lower than that of the resist and a dry etching rate selectivity lower than that of the semiconductor substrate. it can.
- the resist underlayer film formed from the resist underlayer film forming composition of the present invention has an effect as a flattening film and an antireflection film, and has heat resistance, and does not cause intermixing with the resist composition. Therefore, it can be effectively used for forming a fine pattern in the lithography process of the semiconductor device.
- the resist underlayer film material of the present invention has heat resistance capable of forming a hard mask on the upper layer by vapor deposition.
- the polymer containing the unit structure represented by the formula (1), formula (2) and formula (3) of the present invention is excellent in transparency and heat resistance in the visible range, has a high refractive index, and Excellent solubility in various solvents, so protective films for liquid crystal display elements, TFT array flattening films, overcoats such as color filters, spacer materials, light extraction improving films for EL displays, and improved light intake for imaging elements It can be applied as a high refractive index film widely used for optical members such as a layer, a light extraction improving layer in an LED element, and a high refractive index film forming composition for forming the same.
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Abstract
Description
また、プリント配線板等の絶縁材料に使用される、高耐熱性を有するカルバゾールとアセトアルデヒドを用いたノボラック樹脂(特許文献8参照)が開示されている。
また、本発明の目的は、カルバゾールノボラック樹脂の特異な性質を用いて、可視領域での透明性高屈折率膜及びそれを形成するための高屈折率膜形成組成物、並びに該高屈折率膜を含む電子デバイスを提供することである。
R3は水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群から選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基を表し、
R4はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数6乃至40のアリール基又は複素環基を表し、
R5は水素原子、又はハロゲン基、ニトロ基、アミノ基、若しくはヒドロキシ基で置換されていても良い、炭素原子数1乃至10のアルキル基、炭素原子数6乃至40のアリール基又は複素環基を表し、そして
R4とR5はそれらが結合する炭素原子と一緒になって環を形成していても良く、
n1及びn2はそれぞれ1乃至3の整数である。)で表される単位構造を含むポリマー、
第2観点として、前記式(1)中、R1、R2、R3、及びR5はそれぞれ水素原子を表し、R4はフェニル基又はナフチル基で表される単位構造を含む、第1観点に記載のポリマー、
第3観点として、前記式(1)中、R1、R2、及びR3はそれぞれ水素原子を表し、そしてR4及びR5はそれらが結合する炭素原子と一緒になってフルオレン環を形成し、その際、該炭素原子は形成されたフルオレン環の9位の炭素原子である単位構造を含む、第1観点に記載のポリマー、
第4観点として、下記式(2)及び/又は式(3):
R3は水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群から選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基を表し、
R4はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数6乃至40のアリール基又は複素環基を表し、
R5は水素原子、又はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数1乃至10のアルキル基、炭素原子数6乃至40のアリール基又は複素環基を表し、そして
R4とR5はそれらが結合する炭素原子と一緒になって環を形成していても良く、
n1及びn2はそれぞれ1乃至3の整数であり、
n3乃至n5はそれぞれ1乃至4の整数である。)で示される単位構造を含むポリマー、
第5観点として、前記式(2)及び/又は前記式(3)中、R1、R2、R3、R5、R6、R7、及びR8はそれぞれ水素原子であり、R4はフェニル基又はナフチル基である単位構造を含む、第4観点記載のポリマー、
第6観点として、第1観点乃至第5観点のいずれか一つに記載のポリマーを含むレジスト下層膜形成組成物、
第7観点として、更に架橋剤を含む、第6観点に記載のレジスト下層膜形成組成物、
第8観点として、更に酸及び/又は酸発生剤を含む、第6観点又は第7観点に記載のレジスト下層膜形成組成物、
第9観点として、第6観点乃至第8観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって形成される、レジスト下層膜、
第10観点として、第6観点乃至第8観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成して下層膜を形成する工程を含む、半導体の製造に用いられるレジストパターンの形成方法、
第11観点として、第6観点乃至第8観点のいずれか一つに記載のレジスト下層膜形成組成物によりレジスト下層膜を半導体基板上に形成する工程、該レジスト下層膜上にレジスト膜を形成する工程、光又は電子線の照射及び現像により該レジスト膜にレジストパターンを形成する工程、レジストパターンに従い該下層膜をエッチングする工程、及びパターン化された該下層膜を利用して半導体基板を加工する工程、を含む半導体装置の製造方法、
第12観点として、第6観点乃至第8観点のいずれか一つに記載のレジスト下層膜形成組成物によりレジスト下層膜を半導体基板上に形成する工程、該レジスト下層膜上にハードマスクを形成する工程、更に該ハードマスク上にレジスト膜を形成する工程、光又は電子線の照射及び現像により該レジスト膜にレジストパターンを形成する工程、レジストパターンに従いハードマスクをエッチングする工程、該パターン化されたハードマスクに従い該下層膜をエッチングする工程、及び該パターン化された下層膜を利用して半導体基板を加工する工程、を含む半導体装置の製造方法、
第13観点として、前記ハードマスクが、レジスト下層膜上に無機物を蒸着して形成される、第12観点に記載の製造方法、
第14観点として、式(1)で表される単位構造、式(2)で表される単位構造、及び式(3)で表される単位構造からなる群より選ばれる少なくとも1種の単位構造を含むポリマーを含む高屈折率膜形成組成物、
第15観点として、第14観点に記載の高屈折率膜形成組成物を塗布して形成される高屈折率膜、並びに
第16観点として、第15観点に記載の高屈折率膜を含む電子デバイス、
に関する。
本発明は、上記式(1)で表される単位構造を含むポリマー、又は本発明は式(2)及び/又は式(3)で表される単位構造を含むポリマー、即ち、特定の構造を含むカルバゾールノボラック樹脂に関する。
式(1)中、R3としては、水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群より選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基が挙げられる。
式(1)中、R4としては、ハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数6乃至40のアリール基又は複素環基が挙げられる。
式(1)中、R5としては、水素原子、又はハロゲン基、ニトロ基、アミノ基、若しくはヒドロキシ基で置換されていても良い、炭素原子数1乃至10のアルキル基、炭素原子数6乃至40のアリール基又は複素環基が挙げられる。また、R4とR5はそれらが結合する炭素原子と一緒になって環を形成していても良い。これらの環としては、例えばR4及びR5が結合する炭素原子と一緒になって形成したフルオレン環であって、該炭素原子が形成したフルオレン環の9位の炭素原子であるフルオレン環が挙げられる。n1及びn2はそれぞれ1乃至3の整数である。
式(2)及び式(3)中、R3としては、水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組合せからなる群より選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基が挙げられる。
式(2)及び式(3)中、R4としては、ハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数6乃至40のアリール基又は複素環基が挙げられる。
式(2)及び式(3)中、R5としては、水素原子、又はハロゲン基、ニトロ基、アミノ基、若しくはヒドロキシ基で置換されていても良い、炭素原子数1乃至10のアルキル基、炭素原子数6乃至40のアリール基又は複素環基が挙げられる。そして、R4とR5はそれらが結合した炭素原子と一緒になって環を形成していても良い。これらの環としては、例えばR4及びR5はそれらが結合した炭素原子と一緒なって形成したフルオレン環であって、該炭素原子は形成された該フルオレン環の9位の炭素原子であるフルオレン環構造等が挙げられる。
n1及びn2はそれぞれ1乃至3の整数であり、n3乃至n5はそれぞれ1乃至4の整数である。
上記連鎖移動剤としては、ドデカンチオール及びドデシルチオール等が挙げられる。
上記重合開始剤としては、アゾビスイソブチロニトリル及びアゾビスシクロヘキサンカルボニトリル等が挙げられる。
上記重合停止剤としては、4-メトキシフェノール等が挙げられる。
上記重合反応の反応温度としては30乃至100℃、反応時間としては1乃至48時間から適宜選択される。
本発明は上述した式(1)で表される単位構造を含むポリマー、又は式(2)及び/又は式(3)で示される単位構造を含むポリマーを含むレジスト下層膜形成組成物に関する。
式(5)中、R11は水素原子又は炭素原子数1乃至10のアルキル基を表し、R12は炭素原子数1乃至10のアルキル基を表し、n11は1乃至4の整数であり、n12は0乃至(4-n11)であり、(n11+n12)は1乃至4の整数である。
式(5)の単位構造を有するポリマー又はオリゴマーは、繰り返し数が2乃至100、又は2乃至50の範囲が好ましい。
R9乃至R11を表すアルキル基及びアリール基としては、上述したアルキル基及びアリール基を例示することができる。
上記界面活性剤としては、例えばポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類、ポリオキシエチレンオクチルフエノールエーテル、ポリオキシエチレンノニルフエノールエーテル等のポリオキシエチレンアルキルアリルエーテル類、ポリオキシエチレン・ポリオキシプロピレンブロツクコポリマー類、ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタントリオレエート、ソルビタントリステアレート等のソルビタン脂肪酸エステル類、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレエート、ポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤、エフトツプEF301、EF303、EF352((株)トーケムプロダクツ製、商品名)、メガファックF171、F173、R-30(大日本インキ(株)製、商品名)、フロラードFC430、FC431(住友スリーエム(株)製、商品名)、アサヒガードAG710、サーフロンSー382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(株)製、商品名)等のフッ素系界面活性剤、オルガノシロキサンポリマーKP341(信越化学工業(株)製)等が挙げられる。
本発明のレジスト下層膜形成組成物から、半導体装置の製造における、リソグラフィープロセスに用いるレジスト下層膜を形成できる。
リソグラフィー工程において、本発明のレジスト膜を用いることで、微細なレジストパターンを形成することが可能となる。
以下、本発明のレジストパターン形成法について説明する。まず、基板上に上述したようにレジスト下層膜を作成する。次に、レジスト下層膜上に直接、又は必要に応じて1層乃至数層の、塗膜材料をレジスト下層膜上に塗布し硬化させた膜上に、レジスト形成組成物を塗布し硬化させる。形成されたレジストにパターンが描かれた所定のマスクを通して、光又は電子線の照射し、現像し、リンスし、乾燥することにより良好なレジストパターンを得ることができる。必要に応じて光又は電子線の照射後加熱(PEB:Post Exposure Bake)を行うこともできる。次に、パターン化されたレジストをマスクとしてドライエッチングを行うことにより、レジスト下層膜が除去され、所望のパターンが基板上に転写される。
本発明におけるレジスト下層膜の上部に塗布されるフォトレジストとしてはネガ型、ポジ型いずれも使用でき、例えば、ノボラック樹脂と1,2-ナフトキノンジアジドスルホン酸エステルとからなるポジ型フォトレジスト、酸により分解してアルカリ溶解速度を上昇させる基を有するバインダーと光酸発生剤からなる化学増幅型フォトレジスト、アルカリ可溶性バインダーと酸により分解してフォトレジストのアルカリ溶解速度を上昇させる低分子化合物と光酸発生剤からなる化学増幅型フォトレジスト、酸により分解してアルカリ溶解速度を上昇させる基を有するバインダーと酸により分解してフォトレジストのアルカリ溶解速度を上昇させる低分子化合物と光酸発生剤からなる化学増幅型フォトレジスト、骨格にSi原子を有するフォトレジスト等が挙げられる。例えば、t-BOCで保護したポリビニルフェノール樹脂と酸発生剤とからなる化学増幅型レジストとして、ロームアンドハース社製、商品名APEX-Eが挙げられる。
次に、上述したレジスト下層膜形成組成物を用いた、半導体装置の製造方法について説明する。
一般に、半導体装置は、レジスト下層膜形成組成物によりレジスト下層膜を半導体基板上に形成する工程、該レジスト下層膜上にレジスト膜を形成する工程、パターンが描かれたマスクを用いた光又は電子線の照射及び現像により該レジスト膜にレジストパターンを形成する工程、該レジストパターンに従って、該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜を利用して半導体基板を加工する工程を経て製造することができる。
本発明において、高屈折率膜形成組成物は上記ポリマー及び溶剤を含む。また、高屈折率膜としての効果を損なわない範囲で、その他の成分、例えば上記の架橋剤、酸発生剤、界面活性剤、レベリング剤等が含まれていてもよい。
なかでも、本発明の高屈折率膜形成組成物に用いるポリマーに含まれる複素環基としては、硫黄原子を含む複素環基が好ましい。
光重合開始剤は、(メタ)アクリレート化合物100質量部に対して、0.1乃至15質部の範囲で使用することが好ましく、より好ましくは1乃至10質量部の範囲である。
本発明の高屈折率形成組成物を基板等に塗布し、硬化させることで高屈折率膜が得られる。
さらに、本発明の高屈折率膜は、高耐熱性、高透明性を維持でき、これまで、耐熱性及び透明性が損なわれると考えられていたモノマーユニットを用いた場合でも、ポリマー骨格を本発明の部分構造に変更するのみで物性をコントロールできる可能性がある。即ち、本発明の高屈折率膜は、含まれるポリマーの、合成時の出発原料であるモノマーの種類を変更することで諸物性をコントロールできる。
例えば、本発明のカルバゾール環含有ポリマー、又はカルバゾール環及びトリフェニルアミン環含有ポリマーは高耐熱性絶縁材料として使用できる。
[1H NMR]
装置:JEOL-ECP300(300MHz)
測定溶剤:CDCl3、DMSO-d6
基準物質:テトラメチルシラン(TMS)(δ0.0ppm)
[重量平均分子量]
装置:東ソー(株)製 HLC-8200 GPC
カラム:Shodex KF-804L+KF-805L
カラム温度:40℃
溶剤:テトラヒドロフラン
検出器:UV(254nm)
検量線:標準ポリスチレン
[5%重量減少温度]
装置:(株)リガク製 TG-8120
昇温速度:10℃/分
測定温度:25℃-750℃
[ガラス転移温度]
装置:(株)NETZSCH製 Photo-DSC 204 F1 Phoenix
昇温速度:40℃/分
測定温度:25℃-350℃
[屈折率、膜厚]
装置:ジェー・エー・ウーラム・ジャパン社製 多入射角分光エリプソメーターVASE
[光透過率]
装置:(株)島津製作所製 SHIMADZU UV-3600
[エッチング速度]
装置:日本サイエンティフィック製 ES401
エッチングガス:CF4
窒素雰囲気下、100mL四口フラスコにカルバゾール(10.0g、59.8mmol、東京化成工業(株)製)、ベンズアルデヒド(6.41g、60.4mmol、純正化学(株)製)、パラトルエンスルホン酸一水和物(1.19g、62.6mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(15g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、2時間重合反応を行った。反応終了後、60℃まで放冷し、ここへクロロホルム(50g、関東化学(株)製)を加え希釈し、この溶液をメタノール(250g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、10時間乾燥し、更に120℃、24時間乾燥して、目的とするポリマー(式(1-1)、以下PCzBAと略す)8.64gを得た。
PCzBAの1H-NMRスペクトルの測定結果を図1に示す。
PCzBAの1H-NMRの測定結果は以下の通りであった。
1H-NMR(300MHz,DMSO-d6):δ5.29-6.40(br,1H),δ6.41-7.53(br,9H),δ7.54-8.34(br,2H),δ10.49-11.46(br,1H)
PCzBAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは4000、多分散度Mw/Mnは1.69であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(8.0g、47.8mmol、東京化成工業(株)製)、1-ナフトアルデヒド(7.55g、48.3mmol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.95g、50.0mmol、関東化学(株)製)を加えた。更に、1,4-ジオキサン(8g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、4時間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(40g、関東化学(株)製)を加え希釈し、この溶液をメタノール(200g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、10時間乾燥し、更に120℃、24時間乾燥して、目的とするポリマー(式(1-2)、以下PCzNAと略す)10.03gを得た。
PCzNAの1H-NMRスペクトルの測定結果を図2に示す。
PCzNAの1H-NMRの測定結果は以下の通りであった。
1H-NMR(300MHz,DMSO-d6):δ6.01-7.57(br,9H),δ7.58-8.57(br,5H),δ10.75-11.63(br,1H)
PCzNAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2600、多分散度Mw/Mnは1.30であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(8.2g、49.0mmol、東京化成工業(株)製)、ベンズアルデヒド(6.49g、61.2mmol、東京化成工業(株)製)、トリフェニルアミン(3.0g、12.2mmol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.22g、6.4mmol、関東化学(株)製)を加えた。更に、1,4-ジオキサン(15g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、1.5時間重合反応を行った。反応終了後30℃まで放冷し、クロロホルム(60g、関東化学(株)製)を加え希釈し、この溶液をメタノール(300g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、10時間乾燥し、更に120℃、24時間乾燥させ、目的とするポリマー(式(2-1)と式(3-1)の混合物、以下PTPABACzと略す)11.74gを得た。
PTPABACzの1H-NMRスペクトルの測定結果を図3に示す。
PTPABACzの1H-NMRの測定結果は以下の通りであった。
1H-NMR(300MHz,DMSO-d6):δ4.74-6.36(br,1.2H),δ6.38-7.54(br,12H),δ7.57-8.31(br,2H),δ10.48-11.50(br,1H)
PTPABACzのGPCによるポリスチレン換算で測定される重量平均分子量Mwは6400、多分散度Mw/Mnは1.93であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(6.7g、40.0mmol、東京化成工業(株)製)、9-フルオレノン(7.28g、40.4mmol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、40.0mmol、東京化成工業(株)製)を加えた。更に、1,4-ジオキサン(6.69g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、24時間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(34g、関東化学(株)製)を加え希釈し、この溶液をメタノール(168g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥して、目的とするポリマー(式(1-5)、以下PCzFLと略す)9.37gを得た。
PCzFLの1H-NMRスペクトルの測定結果を図4に示す。
PCzFLの1H-NMRの測定結果は以下の通りであった。
1H-NMR(400MHz,DMSO-d6):δ7.03-7.55(br,12H),δ7.61-8.10(br,4H),δ11.18(br,1H)
PCzFLのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2800、多分散度Mw/Mnは1.77であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(10.0g、59.8mmol、東京化成工業(株)製)、ベンズアルデヒド(6.41g、60.4mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(1.19g、62.6mmol、関東化学(株)製)を加えた。更に、1,4-ジオキサン(10.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、1時間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(50g、関東化学(株)製)を加え希釈し、この溶液をメタノール(250g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、クロロホルム(20g)に再溶解させ、この溶液をメタノール(250g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-1)、以下PCzBAと略す)9.86gを得た。
得られたPCzBAの1H NMRスペクトルを図5に示す。また、PCzBAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは4,100、多分散度Mw/Mnは1.55であった。
窒素雰囲気下、1L四口フラスコにカルバゾール(100.0g、598mmol、東京化成工業(株)製)、1-ナフトアルデヒド(94.3g、604mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(11.9g、59.8mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(100.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、5時間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(500g、関東化学(株)製)を加え希釈し、この溶液をメタノール(2500g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、クロロホルム(300g)に再溶解させ、メタノール(2500g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥し、目的とするポリマー(式(1-2)、以下PCzNAと略す)95.5gを得た。
得られたPCzNAの1H NMRスペクトルを図6に示す。また、PCzNAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2,100、多分散度Mw/Mnは1.34であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(5.0g、0.0179mol、東京化成工業(株)製)、9-アントラセンカルボキシアルデヒド(3.74g、0.0181mol(カルバゾールに対して1.01eq)、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(1.25g、0.00657mol(0.37eq)、関東化学(株)製)を加た。更に1,4-ジオキサン(3.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、7時間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(10g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-6)、以下PCzAAと略す)4.13gを得た。
得られたPCzAAの1H NMRスペクトルを図7に示す。また、PCzAAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2,100、多分散度Mw/Mnは1.77であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(5.0g、29.9mmol、東京化成工業(株)製)、4-フェニルベンズアルデヒド(5.50g、30.2mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(2.09g、6.57mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(5.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、20分間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(25g、関東化学(株)製)を加え希釈し、この溶液をメタノール(125g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物をろ過し、クロロホルム(25g)に再溶解させ、メタノール(125g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-7)、以下PCzPBAと略す)7.75gを得た。
得られたPCzPBAの1H NMRスペクトルを図8に示す。また、PCzPBAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは3,800、多分散度Mw/Mnは1.52であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(5.0g、29.9mmol、東京化成工業(株)製)、p-アニスアルデヒド(4.11g、30.2mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(2.11g、11.1mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(5.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、30分間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(10g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、クロロホルム(10g)に再溶解させ、メタノール(100g、関東化学(株)製)へ再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-10)、以下PCzpAAと略す)4.17gを得た。
得られたPCzpAAの1H NMRスペクトルを図9に示す。また、PCzpAAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2,800、多分散度Mw/Mnは1.96であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(3.0g、17.9mmol、東京化成工業(株)製)、3-チオフェンアルデヒド(2.03g、18.1mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(0.34g、1.79mmol、関東化学(株)製)を加えた。更に、1,4-ジオキサン(3.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、30分間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(10g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物をろ過し、クロロホルム(8g)に再溶解させ、メタノール(100g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-8)、以下PCzTAと略す)3.11gを得た。
得られたPCzTAの1H NMRスペクトルを図10に示す。また、PCzTAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは4,800、多分散度Mw/Mnは1.85であった。
窒素雰囲気下、100mL四口フラスコにカルバゾール(3.0g、17.9mmol、東京化成工業(株)製)、テレフタルアルデヒド(1.22g、9.15mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(0.36g、1.88mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(3.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、30分間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(10g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物をろ過し、クロロホルム(8g)に再溶解させ、メタノール(100g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥し、目的とするポリマー(式(1-11)、以下PCzTPAと略す)2.62gを得た。
得られたPCzTPAの1H NMRスペクトルを図11に示す。また、PCzTPAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは6,300、多分散度Mw/Mnは2.50であった。
窒素雰囲気下、100mL四口フラスコに9-エチルカルバゾール(3.0g、15.4mmol、東京化成工業(株)製)、ベンズアルデヒド(1.65g、15.5mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(0.29g、1.54mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(3.0g、関東化学(株)製)を加え、撹拌しながら110℃まで昇温し、4時間重合反応を行った。反応終了後60℃まで放冷し、THF(10g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、THF(10g、関東化学(株)製)に再溶解させ、メタノール(60g、関東化学(株)製)とTHF(30g、関東化学(株)製)の混合溶剤へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-12)、以下PEtCzBAと略す)2.60gを得た。
得られたPEtCzBAの1H NMRスペクトルを図12に示す。また、PEtCzBAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1,200、多分散度Mw/Mnは1.27であった。
窒素下、100mL四口フラスコに9-エチルカルバゾール(3.0g、15.4mmol、東京化成工業(株)製)、1-ナフトアルデヒド(2.42g、15.5mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(0.29g、1.54mmol、関東化学(株)製)を加た。更に、1,4-ジオキサン(3.0g、関東化学(株)製)を加え、撹拌しながら、110℃まで昇温し、12時間重合反応を行った。反応終了後60℃まで放冷し、THF(10g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ沈殿させた。得られた沈殿物をろ過し、THF(10g、関東化学(株)製)に再溶解させ、メタノール(60g、関東化学(株)製)とTHF(30g、関東化学(株)製)の混合溶剤へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(式(1-13)、以下PEtCzNAと略す)2.61gを得た。
得られたPEtCzNAの1H NMRスペクトルを図13に示す。また、PEtCzNAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1,000、多分散度Mw/Mnは1.29であった。
窒素雰囲気下、100mL四口フラスコにジフェニルアミン(2.0g、11.8mmol、東京化成工業(株)製)、ベンズアルデヒド(1.27g、11.9mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(0.25g、1.32mol、関東化学(株)製)を加えた。更に1,4-ジオキサン(4.0g、関東化学(株)製)を加えて撹拌しながら100℃まで昇温し、45分間重合反応を行った。反応終了後60℃まで放冷し、クロロホルム(20g、関東化学(株)製)を加え希釈し、この溶液をメタノール(100g、関東化学(株)製)へ加えて沈殿させた。得られた沈殿物をろ過し、クロロホルム(8g)に再溶解させ、メタノール(100g、関東化学(株)製)へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥して、目的とするポリマー(以下PDPABAと略す)2.27gを得た。
得られたPDPABAの1H NMRスペクトルを図14に示す。また、PDPABAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは9,900、多分散度Mw/Mnは2.47であった。
窒素雰囲気下、100mL四口フラスコにフェノール(2.0g、21.3mmol、純正化学(株)製)、ベンズアルデヒド(4.51g、42.5mmol、純正化学(株)製)、及びパラトルエンスルホン酸一水和物(4.06g、21.3mmol、関東化学(株)製)を加えた。更に1,4-ジオキサン(4.0g、関東化学(株)製)を加え、撹拌しながら100℃まで昇温し、1時間重合反応を行った。反応終了後60℃まで放冷し、この溶液を純水(200g)とメタノール(40g、関東化学(株)製)の混合溶剤へ加えて再沈殿させた。得られた沈殿物をろ過し、クロロホルム(20g)に再溶解させ、純水(200g)とメタノール(40g、関東化学(株)製)の混合溶剤へ加えて再沈殿させた。得られた沈殿物を再度ろ過し、減圧乾燥機で60℃、10時間乾燥し、目的とするポリマー(以下PPBAと略す)3.88gを得た。
得られたPPBAの1H NMRスペクトルを図15に示す。また、PPBAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは23,000、多分散度Mw/Mnは6.24であった。
合成例1で合成したPCzBA20gに、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させ。その溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例1で合成したPCzBA20gに、架橋剤としてTM-BIP-A(旭有機材工業(株)製、商品名)2.0g、触媒としてピリジニウムパラトルエンスルホネート0.10g、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート88gに溶解させた。この溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例2で得たPCzNA20gに、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させた。その溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例3で得たPTPABACz20gに、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させた。この溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例4で得たPCzFL20gに、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させた。この溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例4で得たPCzFL20gに、架橋剤としてテトラメトキシメチルグリコールウリル(三井サイテック(株)製、商品名パウダーリンク1174)3.0g、触媒としてピリジニウムパラトルエンスルホネート0.30g、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート88gに溶解させた。この溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
市販のクレゾールノボラック樹脂(クレゾールとホルムアルデヒドを用いて得られたノボラック樹脂)20gに、界面活性剤としてメガファックR-30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させた。この溶液を、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。クレゾールノボラック樹脂のGPCによるポリスチレン換算で測定される重量平均分子量Mwは4000、多分散度Mw/Mnは2.1であった。
実施例1乃至6で調製したレジスト下層膜溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布し、ホットプレート上で240℃1分間、又は400℃2分間焼成して、レジスト下層膜(膜厚0.25μm)を形成した。これらのレジスト下層膜を、分光エリプソメ-タ-を用いて波長248nm及び波長193nmでの屈折率(n値)及び光学吸光係数(k値、減衰係数とも呼ぶ)を測定した。結果を表1に示した。
実施例1乃至6及び比較例1で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布し、ホットプレート上で400℃2分間焼成し、レジスト下層膜(膜厚0.25μm)を形成した。これらレジスト下層膜をレジストに使用する溶剤である、乳酸エチル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、及びシクロヘキサノンに浸漬した。これらレジスト下層膜はこれら溶剤に不溶であった。
実施例1乃至6及び比較例1で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布し、ホットプレート上で240℃1分間、又は400℃2分間焼成して、レジスト下層膜(膜厚0.25μm)を形成した。また、同様にフェノ-ルノボラック樹脂(市販品、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.5)溶液を、スピンコーターを用いてシリコンウェハー上に塗布し、205℃1分間焼成して塗膜を形成した。形成したレジスト下層膜のエッチング速度を測定した。エッチングガスとしてはCF4ガスを使用してドライエッチング速度を測定した。
205℃1分間焼成して得られたフェノールノボラック樹脂膜(膜厚0.25μm)のエッチング速度を1.00とした時の実施例1乃至6及び比較例1のレジスト下層膜のドライエッチング速度との比較を行った。結果を表2に示した。ドライエッチング速度比は(レジスト下層膜のドライエッチング速度)/(フェノ-ルノボラック樹脂膜のドライエッチング速度)より求めた。
実施例1乃至6及び比較例1で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布し、ホットプレート上で240℃1分間又は400℃2分間焼成して、レジスト下層膜(膜厚0.25μm)を形成した。得られた膜を室温(約20℃)から一分間に10℃ずつの割合で昇温加熱して大気中で熱重量分析を行い、重量が5パ-セント減少する温度を測定した。結果を表3に示す。
合成例5乃至13、及び比較合成例1又は2で得られた各ポリマーについて、5%重量減少温度(Td5%)及びガラス転移温度(Tg)を測定した。結果を表4に示す。
合成例5乃至13、及び比較合成例1又は2で得られた各ポリマー10質量部を、プロピレングリコールモノメチルエーテル(PGME)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、シクロヘキサノン(CHN)又はN-メチル-2-ピロリドン(NMP)90質量部にそれぞれ加え、室温(およそ25℃)で24時間撹拌して、溶剤溶解性を評価した。評価は目視で行い、均一に溶解したものを○、不溶物があるものを×とした。結果を表5に示す。
<実施例7乃至15>
空気下、10mLナスフラスコに、それぞれ合成例5乃至13で得られたポリマー1.00g、及びシクロヘキサノン9.00gを加えた。それぞれの混合物を、溶液が均一になるまで3時間撹拌し、樹脂濃度が10質量%である高屈折率膜形成組成物を得た。
得られた高屈折率膜形成組成物を、ガラス基板上にスピンコート法(200rpm×5秒間、次いで2,000rpm×30秒間)により塗布し、100℃のホットプレートで1分間、更に250℃で5分間加熱して、高屈折率膜を得た。
使用するポリマーを比較合成例1又は2で得られた各ノボラック樹脂に代えて、実施例7乃至15と同様の手順で、膜形成組成物及びそれから形成される薄膜を作製した。
実施例7乃至15で調製した高屈折率膜形成組成物をそれぞれバイアル瓶に入れ、23℃55RH%の条件に静置した。そのまま1ヶ月経過後、目視で観察したところ、何れの高屈折率膜形成組成物においても溶質が析出しなかった。これより、高屈折率膜形成組成物は保存安定性に優れていることが理解される。
実施例7乃至15、及び比較例2又は3で得られた(高屈折率)膜それぞれについて、膜厚、並びに波長550nm及び633nmにおける屈折率を測定した。結果を表6に示す。また、各薄膜の波長300nm乃至800nmの光透過スペクトルを、それぞれ図16乃至図26に示す。
また、図16乃至図26に示した光透過スペクトルより、本発明のカルバゾールノボラック樹脂は特に可視光領域において高い透明性を有することがわかる。
また本発明の式(1)、式(2)及び式(3)で表される単位構造を含むポリマーは、可視域での透明性と耐熱性に優れ、高い屈折率を有し、かつ、様々な溶剤への溶解性に優れているため、液晶表示素子の保護膜、TFTアレイ平坦化膜、カラーフィルター等のオーバーコート、スペーサー材、ELディスプレイの光取り出し向上膜、撮像素子の光取り入れ向上層、LED素子における光取り向上層等、広く光学部材に用いられる高屈折率膜及びそれを形成するための高屈折率膜形成組成物として応用可能である。
Claims (16)
- 下記式(1):
R1及びR2はそれぞれ水素原子、ハロゲン基、ニトロ基、アミノ基、ヒドロキシ基、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群より選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基を表し、
R3は水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群より選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基を表し、
R4はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い炭素原子数6乃至40のアリール基又は複素環基を表し、
R5は水素原子、又はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数1乃至10のアルキル基、炭素原子数6乃至40のアリール基又は複素環基を表し、そして
R4とR5はそれらが結合する炭素原子と一緒になって環を形成してもよく、
n1及びn2はそれぞれ1乃至3の整数である。)で表される単位構造を含むポリマー。 - 前記式(1)中、R1、R2、R3、及びR5はそれぞれ水素原子を表し、R4はフェニル基又はナフチル基を表す単位構造を含む、請求項1に記載のポリマー。
- 前記式(1)中、R1、R2、及びR3はそれぞれ水素原子を表し、そしてR4及びR5はそれらが結合する炭素原子と一緒になってフルオレン環を形成し、その際、該炭素原子は形成された該フルオレン環の9位の炭素原子である単位構造を含む、請求項1に記載のポリマー。
- 下記式(2)及び/又は式(3):
R1、R2、R6、R7、及びR8はそれぞれ水素原子、ハロゲン基、ニトロ基、アミノ基、ヒドロキシ基、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群から選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基を表し、
R3は水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至10のアルケニル基、炭素原子数6乃至40のアリール基、及びそれらの組み合わせからなる群から選択され、かつ、該アルキル基、該アルケニル基又は該アリール基は、エーテル結合、ケトン結合若しくはエステル結合を含んでいても良い基を表し、
R4はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い炭素原子数6乃至40のアリール基又は複素環基を表し、
R5は水素原子、又はハロゲン基、ニトロ基、アミノ基若しくはヒドロキシ基で置換されていても良い、炭素原子数1乃至10のアルキル基、炭素原子数6乃至40のアリール基又は複素環基を表し、そして
R4とR5はそれらが結合する炭素原子と一緒になって環を形成してもよく、
n1及びn2はそれぞれ1乃至3の整数であり、
n3乃至n5はそれぞれ1乃至4の整数である。)で表される単位構造を含むポリマー。 - 前記式(2)及び/又は式(3)中、R1、R2、R3、R5、R6、R7、及びR8はそれぞれ水素原子を表し、R4はフェニル基又はナフチル基を表す単位構造を含む、請求項2に記載のポリマー。
- 請求項1乃至請求項5のいずれか1項に記載のポリマーを含むレジスト下層膜形成組成物。
- 更に架橋剤を含む、請求項6に記載のレジスト下層膜形成組成物。
- 更に酸及び/又は酸発生剤を含む、請求項6又は請求項7に記載のレジスト下層膜形成組成物。
- 請求項6乃至請求項8のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって形成される、レジスト下層膜。
- 請求項6乃至請求項8のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成して下層膜を形成する工程を含む、半導体の製造に用いられるレジストパターンの形成方法。
- 請求項6乃至請求項8のいずれか1項に記載のレジスト下層膜形成組成物によりレジスト下層膜を半導体基板上に形成する工程、該レジスト下層膜上にレジスト膜を形成する工程、光又は電子線の照射及び現像によりレジストパターンを該レジスト膜に形成する工程、レジストパターンに従い該下層膜をエッチングする工程、及び該パターン化されたレジスト下層膜を利用して半導体基板を加工する工程、を含む半導体装置の製造方法。
- 請求項6乃至請求項8のいずれか1項に記載のレジスト下層膜形成組成物によりレジスト下層膜を半導体基板上に形成する工程、該レジスト下層膜上にハードマスクを形成する工程、更に該ハードマスク上にレジスト膜を形成する工程、光又は電子線の照射及び現像によりレジストパターンを該レジスト膜に形成する工程、該レジストパターンに従いハードマスクをエッチングする工程、該パターン化されたハードマスクに従い該レジスト下層膜をエッチングする工程、及び該パターン化されたレジスト下層膜を利用して半導体基板を加工する工程、を含む半導体装置の製造方法。
- 前記ハードマスクが、レジスト下層膜上に無機物を蒸着させて形成されるハードマスクである、請求項12に記載の製造方法。
- 前記式(1)で表される単位構造、前記式(2)で示される単位構造、及び前記式(3)で表される単位構造からなる群より選ばれる少なくとも1種の単位構造を含むポリマーを含む、高屈折率膜形成組成物。
- 請求項14に記載の高屈折率膜形成組成物を塗布して形成される高屈折率膜。
- 請求項15に記載の高屈折率膜を含む、電子デバイス。
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---|---|---|---|---|
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WO2013115097A1 (ja) * | 2012-02-01 | 2013-08-08 | 日産化学工業株式会社 | 複素環を含む共重合樹脂を含むレジスト下層膜形成組成物 |
WO2013146670A1 (ja) * | 2012-03-27 | 2013-10-03 | 日産化学工業株式会社 | フェニルインドール含有ノボラック樹脂を含むレジスト下層膜形成組成物 |
JP2014029435A (ja) * | 2012-07-31 | 2014-02-13 | Nissan Chem Ind Ltd | カルボニル基含有カルバゾールノボラックを含むリソグラフィー用レジスト下層膜形成組成物 |
WO2014092155A1 (ja) * | 2012-12-14 | 2014-06-19 | 日産化学工業株式会社 | カルボニル基含有ポリヒドロキシ芳香環ノボラック樹脂を含むレジスト下層膜形成組成物 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102357731B1 (ko) * | 2012-12-18 | 2022-02-08 | 닛산 가가쿠 가부시키가이샤 | 다환방향족 비닐화합물을 포함하는 자기조직화막의 하층막 형성조성물 |
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KR101798935B1 (ko) | 2015-04-10 | 2017-11-17 | 삼성에스디아이 주식회사 | 유기막 조성물, 유기막, 및 패턴형성방법 |
US9873815B2 (en) * | 2015-04-30 | 2018-01-23 | Samsung Sdi Co., Ltd. | Polymer, organic layer composition, and method of forming patterns |
KR101848343B1 (ko) * | 2015-04-30 | 2018-04-12 | 삼성에스디아이 주식회사 | 중합체, 유기막 조성물, 유기막, 및 패턴형성방법 |
KR101895908B1 (ko) * | 2015-06-10 | 2018-10-24 | 삼성에스디아이 주식회사 | 중합체, 유기막 조성물, 및 패턴형성방법 |
US9971243B2 (en) * | 2015-06-10 | 2018-05-15 | Samsung Sdi Co., Ltd. | Polymer, organic layer composition, organic layer, and method of forming patterns |
KR101884447B1 (ko) * | 2015-07-06 | 2018-08-01 | 삼성에스디아이 주식회사 | 모노머, 유기막 조성물, 유기막, 및 패턴형성방법 |
KR101770749B1 (ko) * | 2016-01-11 | 2017-08-23 | 최상준 | 반사방지용 하드마스크 조성물 |
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CN107340688B (zh) * | 2016-04-29 | 2022-05-06 | 东友精细化工有限公司 | 硬掩模用组合物 |
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US11567408B2 (en) * | 2019-10-15 | 2023-01-31 | Rohm And Haas Electronic Materials Korea Ltd. | Coating composition for use with an overcoated photoresist |
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KR102427439B1 (ko) * | 2020-11-02 | 2022-07-29 | 최상준 | 반사방지용 고분자 및 하드마스크 조성물 |
KR102457955B1 (ko) | 2020-12-21 | 2022-10-24 | (주)코이즈 | 유기 하드마스크용 공중합체 및 이를 포함하는 유기 하드마스크용 조성물 |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01154050A (ja) | 1987-12-10 | 1989-06-16 | Toshiba Corp | パターン形成方法 |
JPH0222657A (ja) | 1988-07-11 | 1990-01-25 | Hitachi Ltd | パターン形成方法および半導体装置製造方法 |
JPH02160731A (ja) * | 1988-08-25 | 1990-06-20 | Gunma Univ | トリアリールメタン構造を有する強磁性有機物質およびその製造方法 |
JPH02293850A (ja) | 1989-05-09 | 1990-12-05 | Toshiba Corp | パターン形成方法 |
JPH10152636A (ja) * | 1991-05-30 | 1998-06-09 | Ricoh Co Ltd | 磁性インク |
JPH10193554A (ja) * | 1997-01-16 | 1998-07-28 | Fuji Photo Film Co Ltd | ネガ型画像記録材料 |
JP2005128509A (ja) | 2003-10-03 | 2005-05-19 | Shin Etsu Chem Co Ltd | フォトレジスト下層膜形成材料及びパターン形成方法 |
JP2007178974A (ja) | 2005-12-26 | 2007-07-12 | Cheil Industries Inc | フォトレジスト下層膜用ハードマスク組成物及びこれを利用した半導体集積回路デバイスの製造方法 |
JP2007199653A (ja) | 2005-12-27 | 2007-08-09 | Shin Etsu Chem Co Ltd | フォトレジスト下層膜形成材料及びパターン形成方法 |
JP2007297540A (ja) | 2006-05-01 | 2007-11-15 | Nippon Steel Chem Co Ltd | カルバゾール骨格含有樹脂、カルバゾール骨格含有エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
US7378217B2 (en) | 2005-09-15 | 2008-05-27 | Cheil Industries, Inc. | Antireflective hardmask composition and methods for using same |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1218286B (de) * | 1963-06-19 | 1966-06-02 | Kalle Ag | Elektrophotographisches Aufzeichnungsmaterial |
US4598139A (en) * | 1984-06-29 | 1986-07-01 | Honeywell Inc. | Complexes of poly (3,6-N-alkylcarbazolyl alkenes) |
US4548738A (en) * | 1984-06-29 | 1985-10-22 | Honeywell Inc. | Electrically conducting complexes of poly (3,6-N-alkylcarbazolyl alkenes) and method of making |
US4631323A (en) * | 1985-07-29 | 1986-12-23 | Honeywell Inc. | Method of making conducting polymer complexes of N-substituted carbazoles and substituted benzaldehydes |
JPS63304247A (ja) * | 1987-06-04 | 1988-12-12 | Konica Corp | 感光性組成物及び感光性平版印刷版 |
CA1305707C (en) * | 1987-06-10 | 1992-07-28 | Yutaka Shikatani | Copolymers and electroactive polymers derived from same |
JPH0668002B2 (ja) * | 1987-06-22 | 1994-08-31 | 日本石油株式会社 | 電気活性ポリマーの製造法およびその製造に適する共重合体の製造法 |
US4954607A (en) | 1988-08-25 | 1990-09-04 | Gunma University | Ferromagnetic organic substance having triaryl methane structure and process for manufacturing the same |
JP2002241455A (ja) * | 2001-02-19 | 2002-08-28 | Fuji Photo Film Co Ltd | 新規重合体、それを利用した発光素子用材料および発光素子 |
JP2003292738A (ja) * | 2002-04-08 | 2003-10-15 | Kyocera Chemical Corp | 封止用樹脂組成物および電子部品封止装置 |
JP4575220B2 (ja) * | 2005-04-14 | 2010-11-04 | 信越化学工業株式会社 | レジスト下層膜材料およびパターン形成方法 |
-
2010
- 2010-06-16 KR KR1020127001404A patent/KR101860385B1/ko active IP Right Grant
- 2010-06-16 WO PCT/JP2010/060223 patent/WO2010147155A1/ja active Application Filing
- 2010-06-16 JP JP2011519817A patent/JP5641253B2/ja active Active
- 2010-06-16 US US13/377,055 patent/US8722841B2/en active Active
- 2010-06-16 CN CN201080027274.XA patent/CN102803324B/zh active Active
- 2010-06-16 EP EP20100789529 patent/EP2444431A4/en not_active Withdrawn
- 2010-06-16 SG SG2011091402A patent/SG176777A1/en unknown
- 2010-06-18 TW TW099119938A patent/TWI500645B/zh active
-
2013
- 2013-01-04 US US13/734,434 patent/US8674052B2/en active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01154050A (ja) | 1987-12-10 | 1989-06-16 | Toshiba Corp | パターン形成方法 |
JPH0222657A (ja) | 1988-07-11 | 1990-01-25 | Hitachi Ltd | パターン形成方法および半導体装置製造方法 |
JPH02160731A (ja) * | 1988-08-25 | 1990-06-20 | Gunma Univ | トリアリールメタン構造を有する強磁性有機物質およびその製造方法 |
JPH02293850A (ja) | 1989-05-09 | 1990-12-05 | Toshiba Corp | パターン形成方法 |
JPH10152636A (ja) * | 1991-05-30 | 1998-06-09 | Ricoh Co Ltd | 磁性インク |
JPH10193554A (ja) * | 1997-01-16 | 1998-07-28 | Fuji Photo Film Co Ltd | ネガ型画像記録材料 |
JP2005128509A (ja) | 2003-10-03 | 2005-05-19 | Shin Etsu Chem Co Ltd | フォトレジスト下層膜形成材料及びパターン形成方法 |
US7378217B2 (en) | 2005-09-15 | 2008-05-27 | Cheil Industries, Inc. | Antireflective hardmask composition and methods for using same |
JP2007178974A (ja) | 2005-12-26 | 2007-07-12 | Cheil Industries Inc | フォトレジスト下層膜用ハードマスク組成物及びこれを利用した半導体集積回路デバイスの製造方法 |
JP2007199653A (ja) | 2005-12-27 | 2007-08-09 | Shin Etsu Chem Co Ltd | フォトレジスト下層膜形成材料及びパターン形成方法 |
JP2007297540A (ja) | 2006-05-01 | 2007-11-15 | Nippon Steel Chem Co Ltd | カルバゾール骨格含有樹脂、カルバゾール骨格含有エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
Non-Patent Citations (2)
Title |
---|
KAZUHIRO TAKAUSU: "Saishin UV Koka Gijutsu", 1991, TECHNICAL INFORMATION INSTITUTE CO., LTD., pages: 159 |
See also references of EP2444431A4 |
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US9892817B2 (en) | 2011-05-25 | 2018-02-13 | Nissan Chemical Industries, Ltd. | Conductive composition, and conductive complex |
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US9343324B2 (en) | 2011-07-07 | 2016-05-17 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition which contains alicyclic skeleton-containing carbazole resin |
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KR20160140596A (ko) | 2014-03-31 | 2016-12-07 | 닛산 가가쿠 고교 가부시키 가이샤 | 방향족 비닐화합물이 부가된 노볼락수지를 포함하는 레지스트 하층막 형성 조성물 |
US9658530B2 (en) | 2014-07-08 | 2017-05-23 | Shin-Etsu Chemical Co., Ltd. | Process for forming multi-layer film and patterning process |
KR20160006122A (ko) | 2014-07-08 | 2016-01-18 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 다층막 형성방법 및 패턴 형성방법 |
KR20170042500A (ko) | 2014-08-08 | 2017-04-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 방향족 메틸올 화합물이 반응된 노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
US11650505B2 (en) | 2014-08-08 | 2023-05-16 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition containing novolac resin reacted with aromatic methylol compound |
US10047244B2 (en) | 2014-08-22 | 2018-08-14 | Shin-Etsu Chemical Co., Ltd. | Method for producing a composition for forming an organic film |
US10323124B2 (en) | 2014-09-30 | 2019-06-18 | Samsung Sdi Co., Ltd. | Polymer, organic layer composition, organic layer, and method of forming patterns |
KR20160045020A (ko) | 2014-10-16 | 2016-04-26 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 다층막 형성방법 및 패턴 형성방법 |
US9804492B2 (en) | 2014-10-16 | 2017-10-31 | Shin-Etsu Chemical Co., Ltd. | Method for forming multi-layer film and patterning process |
US9593205B2 (en) | 2014-11-28 | 2017-03-14 | Samsung Sdi Co., Ltd. | Polymer, organic layer composition, organic layer, and method of forming patterns |
JP2016138945A (ja) * | 2015-01-26 | 2016-08-04 | Jsr株式会社 | 多層レジストプロセス用レジスト下層膜形成組成物及びレジスト下層膜の形成方法 |
JP2016151024A (ja) * | 2015-02-17 | 2016-08-22 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | 重合体、有機膜組成物、有機膜、およびパターン形成方法 |
US9758612B2 (en) | 2015-02-17 | 2017-09-12 | Samsung Sdi Co., Ltd. | Polymer, organic layer composition, organic layer, and method of forming patterns |
US10766973B2 (en) | 2015-06-22 | 2020-09-08 | Maruzen Petrochemical Co., Ltd. | Method for producing polymer for electronic material and polymer for electronic material obtained by the production method |
US10340148B2 (en) | 2015-10-19 | 2019-07-02 | Samsung Sdi Co., Ltd. | Polymer, organic layer composition, and method of forming patterns |
KR20180087331A (ko) | 2015-12-01 | 2018-08-01 | 닛산 가가쿠 고교 가부시키 가이샤 | 인돌로카바졸노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
KR20240024284A (ko) | 2015-12-01 | 2024-02-23 | 닛산 가가쿠 가부시키가이샤 | 인돌로카바졸노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
US11720024B2 (en) | 2015-12-01 | 2023-08-08 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition containing indolocarbazole novolak resin |
US9785049B2 (en) | 2016-01-12 | 2017-10-10 | Shin-Etsu Chemical Co., Ltd. | Method for forming multi-layer film and patterning process |
JPWO2017188263A1 (ja) * | 2016-04-28 | 2019-02-28 | 日産化学株式会社 | 膜密度が向上したレジスト下層膜を形成するための組成物 |
KR20180134863A (ko) | 2016-04-28 | 2018-12-19 | 닛산 가가쿠 가부시키가이샤 | 막밀도가 향상된 레지스트 하층막을 형성하기 위한 조성물 |
WO2017188263A1 (ja) * | 2016-04-28 | 2017-11-02 | 日産化学工業株式会社 | 膜密度が向上したレジスト下層膜を形成するための組成物 |
KR20190013730A (ko) | 2016-05-20 | 2019-02-11 | 닛산 가가쿠 가부시키가이샤 | 레지스트 하층막 형성 조성물 |
US10585353B2 (en) | 2016-05-20 | 2020-03-10 | Nissan Chemical Corporation | Resist underlayer film forming composition |
JP2020501336A (ja) * | 2016-10-13 | 2020-01-16 | ヨンチャン ケミカル カンパニー リミテッドYoung Chang Chemical Co.,Ltd | 高耐エッチング性スピンオンカーボンハードマスク組成物及びそれを用いたパターン化方法 |
JPWO2018164267A1 (ja) * | 2017-03-10 | 2020-01-09 | Jsr株式会社 | レジスト下層膜形成用組成物、レジスト下層膜及びその形成方法並びにパターニングされた基板の製造方法 |
CN110383173B (zh) * | 2017-03-10 | 2023-05-09 | Jsr株式会社 | 抗蚀剂下层膜形成用组合物、抗蚀剂下层膜及其形成方法和形成有图案的基板的制造方法 |
CN110383173A (zh) * | 2017-03-10 | 2019-10-25 | Jsr株式会社 | 抗蚀剂下层膜形成用组合物、抗蚀剂下层膜及其形成方法和形成有图案的基板的制造方法 |
JP7064149B2 (ja) | 2017-03-10 | 2022-05-10 | Jsr株式会社 | レジスト下層膜形成用組成物、レジスト下層膜及びその形成方法並びにパターニングされた基板の製造方法 |
WO2018164267A1 (ja) * | 2017-03-10 | 2018-09-13 | Jsr株式会社 | レジスト下層膜形成用組成物、レジスト下層膜及びその形成方法並びにパターニングされた基板の製造方法 |
US10998197B2 (en) | 2017-08-28 | 2021-05-04 | Shin-Etsu Chemical Co., Ltd. | Polymer and composition for forming organic film, substrate for manufacturing semiconductor apparatus, method for forming organic film, and patterning process |
KR20190024785A (ko) | 2017-08-28 | 2019-03-08 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 유기막 형성용 조성물, 반도체 장치 제조용 기판, 유기막의 형성 방법, 패턴 형성 방법 및 중합체 |
US11181821B2 (en) | 2017-08-30 | 2021-11-23 | Shin-Etsu Chemical Co., Ltd. | Composition for forming organic film, substrate for manufacturing semiconductor apparatus, method for forming organic film, patterning process, and polymer |
KR20190024779A (ko) | 2017-08-30 | 2019-03-08 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 유기막 형성용 조성물, 반도체 장치 제조용 기판, 유기막의 형성 방법, 패턴 형성 방법 및 중합체 |
JP7507919B2 (ja) | 2018-05-01 | 2024-06-28 | 東京応化工業株式会社 | ハードマスク形成用組成物及び電子部品の製造方法 |
JP7256065B2 (ja) | 2018-05-01 | 2023-04-11 | 東京応化工業株式会社 | ハードマスク形成用組成物及び電子部品の製造方法 |
JP2019194693A (ja) * | 2018-05-01 | 2019-11-07 | 東京応化工業株式会社 | ハードマスク形成用組成物及び電子部品の製造方法 |
EP3623867A1 (en) | 2018-09-13 | 2020-03-18 | Shin-Etsu Chemical Co., Ltd. | Patterning process |
JPWO2020122113A1 (ja) * | 2018-12-13 | 2021-10-21 | 日産化学株式会社 | 電荷輸送性ワニス |
JP7351314B2 (ja) | 2018-12-13 | 2023-09-27 | 日産化学株式会社 | 電荷輸送性ワニス |
WO2020122113A1 (ja) * | 2018-12-13 | 2020-06-18 | 日産化学株式会社 | 電荷輸送性ワニス |
EP3761115A1 (en) | 2019-07-05 | 2021-01-06 | Shin-Etsu Chemical Co., Ltd. | Composition for forming organic film, substrate for manufacturing semiconductor device, method for forming organic film, patterning process, and polymer |
US11635691B2 (en) | 2019-07-05 | 2023-04-25 | Shin-Etsu Chemical Co., Ltd. | Composition for forming organic film, substrate for manufacturing semiconductor device, method for forming organic film, patterning process, and polymer |
JP7349887B2 (ja) | 2019-10-31 | 2023-09-25 | 東京応化工業株式会社 | ハードマスク形成用組成物及び電子部品の製造方法 |
JP2021071660A (ja) * | 2019-10-31 | 2021-05-06 | 東京応化工業株式会社 | ハードマスク形成用組成物及び電子部品の製造方法 |
WO2022030469A1 (ja) * | 2020-08-05 | 2022-02-10 | 日産化学株式会社 | レジスト下層膜形成組成物 |
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WO2022138454A1 (ja) * | 2020-12-21 | 2022-06-30 | 日産化学株式会社 | レジスト下層膜形成組成物 |
JP2022099322A (ja) * | 2020-12-22 | 2022-07-04 | 三星エスディアイ株式会社 | ハードマスク組成物およびパターン形成方法 |
US11932715B2 (en) | 2020-12-22 | 2024-03-19 | Samsung Sdi Co., Ltd. | Hardmask composition and method of forming patterns |
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US20120077345A1 (en) | 2012-03-29 |
EP2444431A4 (en) | 2013-12-25 |
CN102803324A (zh) | 2012-11-28 |
US8722841B2 (en) | 2014-05-13 |
JPWO2010147155A1 (ja) | 2012-12-06 |
US20130122710A1 (en) | 2013-05-16 |
CN102803324B (zh) | 2015-09-16 |
SG176777A1 (en) | 2012-01-30 |
JP5641253B2 (ja) | 2014-12-17 |
KR20120038447A (ko) | 2012-04-23 |
TWI500645B (zh) | 2015-09-21 |
EP2444431A1 (en) | 2012-04-25 |
US8674052B2 (en) | 2014-03-18 |
TW201120075A (en) | 2011-06-16 |
KR101860385B1 (ko) | 2018-05-23 |
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