WO2013047516A1 - ジアリールアミンノボラック樹脂 - Google Patents
ジアリールアミンノボラック樹脂 Download PDFInfo
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- WO2013047516A1 WO2013047516A1 PCT/JP2012/074551 JP2012074551W WO2013047516A1 WO 2013047516 A1 WO2013047516 A1 WO 2013047516A1 JP 2012074551 W JP2012074551 W JP 2012074551W WO 2013047516 A1 WO2013047516 A1 WO 2013047516A1
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- 229920003986 novolac Polymers 0.000 title abstract description 28
- 125000005266 diarylamine group Chemical group 0.000 title abstract description 9
- 229920000642 polymer Polymers 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 239000000758 substrate Substances 0.000 claims abstract description 54
- 238000001459 lithography Methods 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000004065 semiconductor Substances 0.000 claims abstract description 41
- 238000005530 etching Methods 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 238000010894 electron beam technology Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 238000011161 development Methods 0.000 claims abstract description 12
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- 239000003431 cross linking reagent Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000000962 organic group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 238000012545 processing Methods 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 238000000059 patterning Methods 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 46
- 239000011347 resin Substances 0.000 abstract description 46
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 abstract description 23
- 239000010408 film Substances 0.000 description 187
- -1 2-methyl-cyclopropyl group Chemical group 0.000 description 185
- 239000000126 substance Substances 0.000 description 32
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- 238000006116 polymerization reaction Methods 0.000 description 13
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- 238000000576 coating method Methods 0.000 description 11
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 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
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-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
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 229920002845 Poly(methacrylic acid) Polymers 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 150000007513 acids Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 150000001716 carbazoles Chemical class 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
- 238000006482 condensation reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 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
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- 230000031700 light absorption Effects 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
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- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 3
- 239000006254 rheological additive 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
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- 150000003672 ureas Chemical class 0.000 description 3
- 229920002554 vinyl polymer Chemical class 0.000 description 3
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- 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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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- 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
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-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
- 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
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- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 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
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- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- 239000004115 Sodium Silicate Substances 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
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- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 2
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- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- HVYCQBKSRWZZGX-UHFFFAOYSA-N naphthalen-1-yl 2-methylprop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C(=C)C)=CC=CC2=C1 HVYCQBKSRWZZGX-UHFFFAOYSA-N 0.000 description 1
- CXAYOCVHDCXPAI-UHFFFAOYSA-N naphthalen-1-yl(phenyl)methanone Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)C1=CC=CC=C1 CXAYOCVHDCXPAI-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- DCUJJWWUNKIJPH-UHFFFAOYSA-N nitrapyrin Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=N1 DCUJJWWUNKIJPH-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- GIPDEPRRXIBGNF-KTKRTIGZSA-N oxolan-2-ylmethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CCCO1 GIPDEPRRXIBGNF-KTKRTIGZSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000141 poly(maleic anhydride) Chemical class 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Chemical class 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C09D161/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
Definitions
- the present invention relates to a diarylamine novolak resin such as phenyl naphthylamine novolak resin. Furthermore, a resist underlayer film forming composition for lithography effective at the time of processing a semiconductor substrate using a diarylamine novolak resin such as phenyl naphthylamine novolak resin, a resist pattern forming method using the resist underlayer film forming composition, and a method for manufacturing a semiconductor device It is about.
- the present invention also relates to a transparent high refractive index film in the visible region using a phenyl naphthylamine novolak resin.
- BARC Bottom Anti-Reflective Coating
- Examples of the polymer for the resist underlayer film include the following.
- a resist underlayer film forming composition using polyvinyl carbazole is exemplified (see Patent Document 1, Patent Document 2, and Patent Document 3).
- a resist underlayer film forming composition using a fluorenephenol novolak resin is disclosed (for example, see Patent Document 4).
- a resist underlayer film forming composition using a fluorene naphthol novolak resin is disclosed (see, for example, Patent Document 5).
- a resist underlayer film forming composition containing a resin having fluorenephenol and arylalkylene as repeating units is disclosed (see, for example, Patent Document 6 and Patent Document 7).
- a novolak resin using phenylnaphthylamine and acetaldehyde is disclosed (see Patent Document 8).
- JP-A-2-293850 Japanese Patent Laid-Open No. 1-154050 JP-A-2-22657 JP 2005-128509 A JP 2007-199653 A JP 2007-178974 A US Pat. No. 7,378,217 JP 2007-297540 A
- the present invention provides diarylamine novolak resins such as novel phenyl naphthylamine novolak resins. Furthermore, this invention is providing the resist underlayer film forming composition used for the lithography process of semiconductor device manufacture using diarylamine novolak resin, such as phenyl naphthylamine novolak resin. In addition, the present invention does not cause intermixing with the resist layer, provides an excellent resist pattern, and has a dry etching rate selection ratio close to that of the resist.
- An object of the present invention is to provide a resist underlayer film for lithography having a ratio and a resist underlayer film for lithography having a low dry etching rate selection ratio as compared with a semiconductor substrate.
- the present invention can also provide the ability to effectively absorb the reflected light from the substrate when using irradiation light having a wavelength of 248 nm, 193 nm, 157 nm or the like for fine processing.
- this invention is providing the formation method of the resist pattern using the resist underlayer film forming composition.
- the resist underlayer film forming composition for forming the resist underlayer film which also has heat resistance is provided.
- a transparent high refractive index film in the visible region and an electronic device using the same are provided using the unique properties of phenylnaphthylamine novolak resin.
- Ar 1 and Ar 2 each represent a benzene ring or a naphthalene ring, and R 1 and R 2 are each a substituent of a hydrogen atom on the ring, 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, an aryl group having 6 to 40 carbon atoms, and a combination thereof, and the alkyl group ,
- the alkenyl group and the aryl group represent an organic group which may contain an ether bond, a ketone bond, or an ester bond
- 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 having 1 to 10 carbon atoms an alkenyl
- R 5 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heterocyclic group, and the alkyl group, the aryl group, and the heterocyclic ring
- the group represents an organic group which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group, and R 4 and R 5 together with the carbon atom to which they are bonded form a ring.
- n 1 and n 2 are each an integer of 0 to 3.
- R 5 in the above formula (1) is a hydrogen atom
- R 4 is an optionally substituted phenyl group, naphthyl group, anthryl group, or pyrenyl group
- R 3 in the above formula (1) is a hydrogen atom or a phenyl group
- any one of Ar 1 and Ar 2 includes the unit structure (a1) in which either one is a benzene ring and the other is a naphthalene ring.
- Ar 1 and Ar 2 each include a unit structure (a2) that forms a benzene ring, the polymer according to any one of the first aspect to the third aspect,
- a polymer that is a copolymer including the unit structure (a1) according to the fourth aspect and the unit structure (a2) according to the fifth aspect As a seventh aspect, the unit structure (A) of the formula (1) described in the first aspect and the unit structure (B) of the following formula (2):
- R 6 is selected from the group consisting of an aryl group having 6 to 40 carbon atoms and a heterocyclic group, and the aryl group and heterocyclic group are a halogen group, a nitro group, and an amino group.
- An organic group which may be substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, a formyl group, a carboxyl group, or a hydroxy group.
- R 7 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heterocyclic group, and the alkyl group, the aryl group, and the A heterocyclic group represents an organic group that may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group, and R 6 and R 7 together with the carbon atom to which they are attached form a ring
- Have Polymer is a copolymer containing also be.
- a polymer that is a copolymer including the unit structure (a1) according to the fourth aspect and the unit structure (B) according to the seventh aspect As a ninth aspect, a resist underlayer film forming composition for lithography comprising the polymer according to any one of the first aspect to the eighth aspect, As a tenth aspect, the resist underlayer film forming composition according to the ninth aspect further including a crosslinking agent, As an
- the resist underlayer film forming composition of the present invention With the resist underlayer film forming composition of the present invention, a good resist pattern shape can be formed without causing intermixing between the upper layer portion of the resist underlayer film and the layer coated thereon.
- the resist underlayer film forming composition of the present invention can be imparted with the ability to efficiently suppress reflection from the substrate, and can also have an effect as an antireflection film for exposure light.
- the resist underlayer film forming composition of the present invention the dry etching rate selectivity close to the resist, the dry etching rate selectivity lower than that of the resist, and the dry etching rate selectivity lower than that of the semiconductor substrate are excellent.
- a resist underlayer film can be provided.
- the resist is thinned.
- the resist pattern is transferred to the lower layer film by an etching process, the substrate processing is performed using the lower layer film as a mask, or the resist pattern is transferred to the lower layer film by an etching process, and further to the lower layer film.
- the resist underlayer film and the composition for forming the resist of the present invention are effective for this process.
- a processed substrate for example, a thermal silicon oxide film on the substrate, silicon nitride) Film, polysilicon film, etc. having sufficient etching resistance.
- the resist underlayer film of the present invention can be used as a planarizing film, a resist underlayer film, a resist layer antifouling film, or a film having dry etch selectivity. This makes it possible to easily and accurately form a resist pattern in a lithography process for manufacturing a semiconductor.
- a resist underlayer film by the resist underlayer film forming composition according to the present invention is formed on a substrate, a hard mask is formed thereon, a resist film is formed thereon, a resist pattern is formed by exposure and development, and a resist pattern Is transferred to the hard mask, the resist pattern transferred to the hard mask is transferred to the resist underlayer film, and the semiconductor substrate is processed with the resist underlayer film.
- the hard mask may be formed by a coating type composition containing an organic polymer or inorganic polymer and a solvent, or by vacuum deposition of an inorganic substance. In the vacuum deposition of an inorganic material (for example, silicon nitride oxide), the deposited material is deposited on the resist underlayer film surface.
- the polymer used is a polymer containing a diarylamine novolak-based unit structure such as phenyl naphthylamine novolak, and therefore has extremely high heat resistance, and thermal degradation does not occur even when deposits are deposited.
- the phenylnaphthylamine novolak resin of the present invention is used for a purpose different from that described above, has excellent transparency and heat resistance in the visible light region, has a high refractive index, and is excellent in solubility in various solvents. Utilizing these characteristics, a protective film for a liquid crystal display element, a TFT array flattening film, an overcoat such as a color filter, a spacer material, a light extraction improving film for an EL display, a light intake improving layer for an imaging element, and light in an LED element It can be widely applied as an optical member such as a take-out improving layer.
- the present invention is a polymer containing the unit structure (A) represented by the formula (1).
- the polymer used in the present invention has a weight average molecular weight of 600 to 1000000 or 600 to 200000.
- the polymer used for this invention contains the repeating unit structure (A) shown by Formula (1).
- Ar 1 and Ar 2 represent a benzene ring and a naphthalene ring, respectively, and R 1 and R 2 are each a substituent of a hydrogen atom on these rings, a halogen group, a nitro group, an amino group, a hydroxy group Selected from the group consisting of a group, 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 and the aryl group represent an organic group that may include an ether bond, a ketone bond, or an ester bond
- 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
- R 5 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heterocyclic group, and the alkyl group, the aryl group, and the heterocyclic ring
- the group is an organic group which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group, and R 4 and R 5 together with the carbon atom to which they are attached form a ring. May be.
- n 1 and n 2 are each an integer of 0 to 3.
- halogen group examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- alkyl group having 1 to 10 carbon atoms include methyl group, ethyl group, n-propyl group, i-propyl group, cyclopropyl group, n-butyl group, i-butyl group, s-butyl group, and t-butyl group.
- Cyclobutyl group 1-methyl-cyclopropyl group, 2-methyl-cyclopropyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 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-dimethyl-cyclopropyl group, 1-ethyl-cyclopropyl group 2-ethyl-cyclopropyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group,
- 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-buten
- the alkoxy group having 1 to 10 carbon atoms is, for example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n -Pentoxy group, 1-methyl-n-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl-n- Propoxy group, 2,2-dimethyl-n-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3 -Methyl-n-pentyloxy, 4-methyl-n-pentyloxy, 1,1-dimethyl-n-butoxy, 1,2-dimethyl-n-butoxy, 1,3-dimethyl-n-but Si group, 2,
- 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 group.
- 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, a pyrazole group, An isoxazole group, an isothiazole group, a pyridine group, etc. are mentioned. Of these, a heterocyclic group containing sulfur is preferable for use in a high refractive index material.
- R 5 is a hydrogen atom
- R 4 may be a phenyl group, naphthyl group, anthryl group, or pyrenyl group which may be substituted.
- R 3 can be a hydrogen atom or a phenyl group.
- the unit structure (a1) in which one of Ar 1 and Ar 2 in the unit structure (A) is a benzene ring and the other is a naphthalene ring can be used.
- a unit structure (a2) in which both Ar 1 and Ar 2 are benzene rings can be used.
- the polymer of the present invention can be a copolymer polymer containing the unit structure (a1) and the unit structure (a2). And it can be set as the copolymer containing the unit structure (A) shown by Formula (1), and the unit structure (B) shown by Formula (2).
- R 6 is selected from the group consisting of an aryl group having 6 to 40 carbon atoms and a heterocyclic group, and the aryl group and heterocyclic group are a halogen group, a nitro group, an amino group Group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, a formyl group, a carboxyl group, or an organic group optionally substituted by a hydroxy group
- R 7 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heterocyclic group, and the alkyl group, the aryl group, and heterocyclic group, a halogen group, a nitro group, an amino group, or hydroxyl group substituted which may be organic groups, and form the R 6 and R 7 together with the carbon atoms to
- the polymer used for this invention can be illustrated below, for example.
- carbazoles are used in the present invention, for example, carbazole, N-methylcarbazole, N-ethylcarbazole, 1,3,6,8-tetranitrocarbazole, 3,6-diaminocarbazole, 3,6-dibromo-9 -Ethylcarbazole, 3,6-dibromo-9-phenylcarbazole, 3,6-dibromocarbazole, 3,6-dichlorocarbazole, 3-amino-9-ethylcarbazole, 3-bromo-9-ethylcarbazole, 4,4 'Bis (9H-carbazol-9-yl) biphenyl, 4-glycidylcarbazole, 4-hydroxycarbazole, 9- (1H-benzotriazol-1-ylmethyl) -9H-carbazole, 9-acetyl-3,6-diiodo Carbazole, 9-benzoylcarbazole, 9-benz
- triphenylamine and substituted triphenylamine are exemplified, and examples of the substituent include the above-mentioned halogen group, nitro group, amino group, hydroxy group, and those having 1 to 10 carbon atoms.
- aldehydes used in the production of the polymer of the present invention include formaldehyde, paraformaldehyde, acetaldehyde, propyl aldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, capronaldehyde, 2-methylbutyraldehyde, hexyl aldehyde, undecane aldehyde, 7-methoxy.
- ketones used for the production of the polymer of the present invention are diaryl ketones, and examples thereof include diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, 9-fluorenone and the like.
- the polymer used in the present invention is a novolak resin (corresponding to the formula (1)) obtained by condensing amines such as diarylamine and aldehydes or ketones. In this condensation reaction, aldehydes or ketones can be used at a ratio of 0.1 to 10 equivalents per 1 equivalent of the phenyl group of amines such as diarylamine.
- 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. Carboxylic acids such as are used.
- the amount of the acid catalyst used is variously selected depending on the type of acids 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 carried out without solvent, but is usually carried out using a solvent. Any solvent that does not inhibit the reaction can be used. 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 obtained as described above is usually 600 to 1000000, or 600 to 200000.
- the present invention can be used as a resist underlayer film for lithography containing the above polymer and a resist underlayer film forming composition for lithography for forming the underlayer film.
- the resist underlayer film forming composition for lithography contains the polymer and a solvent. And it can contain a crosslinking agent and an acid, and can contain additives, such as an acid generator and surfactant, as needed.
- the solid content of the composition is 0.1 to 70% by mass, or 0.1 to 60% by mass.
- the solid content is the content ratio of all components excluding the solvent from the resist underlayer film forming composition.
- the polymer can be contained in a 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 said polymer can mix and use another polymer within 30 mass% in all the polymers.
- These polymers include polyacrylic acid ester compounds, polymethacrylic acid ester compounds, polyacrylamide compounds, polymethacrylamide compounds, polyvinyl compounds, polystyrene compounds, polymaleimide compounds, polymaleic anhydrides, and polyacrylonitrile compounds.
- Examples of the raw material monomer for the polyacrylate compound 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 acrylate 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, 2-propyl-2
- the raw material monomers for the polymethacrylic acid ester 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 , Methoxydiethylene glycol methacrylate, methoxypolyethylene
- 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, and N, N-dimethyl methacrylamide. .
- 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 for the polystyrene compound include styrene, methylstyrene, chlorostyrene, bromostyrene, and hydroxystyrene.
- Examples of the raw material monomer of the polymaleimide compound include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
- polymers are produced by dissolving an addition polymerizable monomer and an optionally added chain transfer agent (10% or less based on the mass of the monomer) in an organic solvent, and then adding a polymerization initiator to perform a polymerization reaction. Thereafter, it can be produced by adding a polymerization terminator.
- the addition amount of the polymerization initiator is 1 to 10% with respect to the mass of the monomer, and the addition amount of the polymerization terminator is 0.01 to 0.2% by mass.
- organic solvent used examples include propylene glycol monomethyl ether, propylene glycol monopropyl ether, ethyl lactate, cyclohexanone, methyl ethyl ketone, and dimethylformamide, chain transfer agents such as dodecane thiol and dodecyl thiol, and polymerization initiators such as azo Examples thereof include bisisobutyronitrile and azobiscyclohexanecarbonitrile, and examples of the polymerization terminator include 4-methoxyphenol.
- the reaction temperature is appropriately selected from 30 to 100 ° C.
- the reaction time is appropriately selected from 1 to 48 hours.
- the resist underlayer film forming composition of the present invention can contain a crosslinking agent component.
- the cross-linking agent include melamine type, substituted urea type, or polymer type thereof.
- a cross-linking agent having at least two cross-linking substituents methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzogwanamine, butoxymethylated benzogwanamine, Compounds such as 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 for example, a benzene ring or a naphthalene ring
- this compound include a compound having a partial structure of the following formula (4) and a polymer or oligomer having a repeating unit of the following formula (5).
- R 9 and R 10 are each 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, and n7 Is an integer from 1 to (5-n6), and (n6 + n7) is an integer from 2 to 5.
- R 11 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- R 12 is an alkyl group having 1 to 10 carbon atoms
- n8 is an integer of 1 to 4
- n9 Is 0 to (4-n8)
- (n8 + n9) is an integer of 1 to 4.
- the oligomer and polymer can be used in the range of 2 to 100 or 2 to 50 repeating unit structures. These alkyl groups and aryl groups can exemplify the above alkyl groups and aryl groups.
- the above compounds can be obtained as products of Asahi Organic Materials Co., Ltd. and Honshu Chemical Industry Co., Ltd.
- the compound of formula (4-21) (Asahi Organic Materials Co., Ltd., trade name TM-BIP-A)
- the compound of formula (4-22) (Honshu Chemical Industry Co., Ltd., The name TMOM-BP)
- the amount of the crosslinking agent to be added varies depending on the coating solvent used, the base substrate used, the required solution viscosity, the required film shape, etc., but is 0.001 to 80% by mass with respect to the total solid content, preferably The amount is 0.01 to 50% by mass, more preferably 0.05 to 40% by mass.
- cross-linking agents may cause a cross-linking reaction by self-condensation, but when a cross-linkable substituent is present in the above-mentioned polymer of the present invention, it can cause a cross-linking reaction with those cross-linkable substituents.
- p-toluenesulfonic acid as a catalyst for promoting the crosslinking reaction, p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid Acidic compounds such as acids or / and thermal acid generators such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters may be added. I can do it.
- the blending amount 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.
- a photoacid generator can be added in order to match the acidity with the photoresist coated on the upper layer 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.
- -Halogen-containing compound photoacid generators such as triazine, and sulfonic acid photoacid generators such as benzoin tosylate and N-hydroxysuccinimide trifluoromethanesulfonate.
- the photoacid generator is 0.2 to 10% by mass, preferably 0.4 to 5% by mass, based on the total solid content.
- the light absorbing agent examples include commercially available light absorbing agents described in “Technical Dye Technology and Market” (published by CMC) and “Dye Handbook” (edited by the Society of Synthetic Organic Chemistry), such as 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.
- Disperse Violet 43; C.I. I. Disperse Blue 96; C.I. I. Fluorescent Brightening Agent 112, 135 and 163; C.I. I. Solvent Orange 2 and 45; C.I. I. Solvent Red 1, 3, 8, 23, 24, 25, 27 and 49; I. Pigment Green 10; C.I. I. Pigment Brown 2 etc. can be used suitably.
- 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 material for lithography.
- the rheology modifier mainly improves the fluidity of the resist underlayer film forming composition, and improves the film thickness uniformity of the resist underlayer film and the fillability of the resist underlayer film forming composition inside the hole, particularly in the baking process. It is added for the purpose of enhancing.
- phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate
- adipic acid derivatives such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decyl adipate
- maleic acid derivatives such as normal butyl maleate, diethyl maleate and dinonyl maleate
- oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate
- stearic acid derivatives such as normal butyl stearate and glyceryl stearate. it can.
- 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 material
- the 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 being peeled off particularly during development.
- 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, ⁇ -chloropropyl
- a surfactant can be blended in order to further improve the applicability to surface unevenness.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol ether.
- polyoxyethylene alkyl aryl ethers such as polyoxyethylene alkyl aryl ethers, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate, etc.
- Sorbitan fatty acid esters polyoxyethylene sorbitan monolaurate, polyoxyethylene
- Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as bitane monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, etc., EFTOP EF301, EF303, EF352 (Trade name, manufactured by Tochem Products Co., Ltd.), MegaFuck F171, F173, R-30 (trade name, manufactured by Dainippon Ink Co., Ltd.), Florad FC430, FC431 (trade name, manufactured by Sumitomo 3M Co., Ltd.) Fluorosurfactants such as Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (trade name, manufactured by Asahi Glass Co., Ltd.), organosiloxane polymer KP341 (S
- 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 material for lithography of the present invention.
- These surfactants may be added alone or in combination of two or more.
- the solvent for dissolving the polymer, the crosslinking agent component, the crosslinking catalyst and the like includes ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate.
- a high boiling point solvent such as propylene glycol monobutyl ether or propylene glycol monobutyl ether acetate can be mixed and used.
- a high boiling point solvent such as propylene glycol monobutyl ether or propylene glycol monobutyl ether acetate
- propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monobutyl ether, ethyl lactate, butyl lactate, and cyclohexanone are preferable for improving the leveling property.
- the resist used in the present invention is a photoresist or an electron beam resist.
- the photoresist applied on the upper part of the resist underlayer film for lithography in the present invention either negative type or positive type can be used, and a positive type photoresist composed of a novolak resin and 1,2-naphthoquinonediazide sulfonic acid ester, depending on the acid.
- 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, and a photoacid generator Chemically amplified photoresist with Si atoms in the skeleton That there is a photoresist or the like, for example, Rohm & Hearts Co., Ltd., and trade name APEX-E.
- an acid is generated by irradiation of a resin containing an Si-Si bond in the main chain and an aromatic ring at the terminal and an electron beam.
- examples include a composition comprising an acid generator, or a composition comprising a poly (p-hydroxystyrene) having a hydroxyl group substituted with an organic group containing N-carboxyamine and an acid generator that generates an acid upon irradiation with an electron beam. It is done.
- 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 into a hydroxyl group and exhibits alkali solubility, thereby exhibiting alkali solubility.
- Acid generators that generate an acid upon irradiation with this electron beam are 1,1-bis (p-chlorophenyl) -2,2,2-trichloroethane and 1,1-bis (p-methoxyphenyl) -2,2,2.
- -Halogenated organic compounds such as trichloroethane, 1,1-bis (p-chlorophenyl) -2,2-dichloroethane, 2-chloro-6- (trichloromethyl) pyridine, triphenylsulfonium salts, diphenyliodonium salts, etc.
- sulfonic acid esters such as onium salts, nitrobenzyl tosylate, and dinitrobenzyl tosylate.
- Alcohol aqueous solutions such as alcohol amines, quaternary ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, and cyclic amines such as pyrrole and piperidine can be used.
- 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.
- a spinner, a coater, etc. are suitably used on a substrate (for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate) used for manufacturing a precision integrated circuit device.
- a substrate for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate
- the resist underlayer film forming composition After applying the resist underlayer film forming composition by a simple coating method, it is baked and cured to form a coating type underlayer film.
- the thickness of the resist underlayer film is preferably 0.01 to 3.0 ⁇ m.
- the conditions for baking after coating are 80 to 350 ° C. and 0.5 to 120 minutes.
- a resist is applied and irradiated with light or an electron beam through a predetermined mask.
- a good resist pattern can be obtained by performing, developing, rinsing and drying. If necessary, post-irradiation heating (PEB: Post Exposure Bake) may be performed. Then, the resist underlayer film where the resist has been developed and removed by the above process is removed by dry etching, and a desired pattern can be formed on the substrate.
- PEB Post Exposure Bake
- the exposure light in 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 is a method capable of generating an acid from a photoacid generator, and the exposure dose 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 of an electron beam resist can be performed using an electron beam irradiation apparatus, for example.
- a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition a step of forming a resist film thereon, a step of forming a resist pattern by light or electron beam irradiation and development, a resist pattern
- a semiconductor device can be manufactured through a step of etching the resist underlayer film and a step of processing the semiconductor substrate with the patterned resist underlayer film.
- the resist underlayer film for lithography which has a selection ratio of dry etching rates close to that of resist, is selected as a resist underlayer film for such processes, and a lower dry etching rate than resist.
- resist underlayer film for lithography having a higher ratio and a resist underlayer film for lithography having a lower dry etching rate selection ratio than a semiconductor substrate.
- a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- a process of making the resist pattern and the resist underlayer film narrower than the pattern width at the time of developing the resist at the time of the resist underlayer film dry etching has begun to be used.
- a resist underlayer film having a selectivity of a dry etching rate close to that of the resist has been required as a resist underlayer film for such a process.
- such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- the substrate can be processed by selecting an appropriate etching gas. That is, a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition, and forming a hard mask by a coating material containing a silicon component or the like or a hard mask (for example, silicon nitride oxide) on the semiconductor substrate.
- a semiconductor device can be manufactured through a step of etching the resist underlayer film with an oxygen-based gas or a hydrogen-based gas and a step of processing a semiconductor substrate with a halogen-based gas with the patterned resist underlayer film.
- the resist underlayer film forming composition for lithography of the present invention has a light absorption site incorporated into the skeleton, so there is no diffused material in the photoresist during heating and drying. Moreover, since the light absorption site has a sufficiently large light absorption performance, the effect of preventing reflected light is high.
- composition for forming a resist underlayer film for lithography of the present invention has high thermal stability, can prevent contamination of the upper layer film by decomposition products during baking, and can provide a margin for the temperature margin of the baking process. is there.
- the resist underlayer film material for lithography has a function of preventing reflection of light depending on process conditions, and further prevents the interaction between the substrate and the photoresist, or a material or photoresist used for the photoresist.
- the film can be used as a film having a function of preventing an adverse effect on a substrate of a substance generated during exposure.
- triphenylamine which 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 described above.
- a ring-containing polymer and a carbazole ring-containing polymer can be provided. That is, a high refractive index film-forming composition containing a polymer (for example, phenyl naphthylamine novolak resin) containing a unit structure represented by the above formula (1) can be obtained. And the said high refractive index film
- the polymer used for this application is a highly branched or linear polymer having a weight average molecular weight of 1,000 to 2,000,000.
- the high refractive index film-forming composition for obtaining the high refractive index film contains a polymer and a solvent, and the solid content concentration is not particularly limited as long as it does not affect the storage stability, and the desired film thickness What is necessary is just to set suitably according to.
- 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 eg, phenyl naphthylamine novolak resin
- other components other than the polymer and the solvent for example, the leveling agent, the surfactant, and the crosslinking agent may be contained.
- the polymer skeleton of the present invention By using the polymer skeleton of the present invention, high heat resistance and high transparency can be maintained, and even when a monomer unit that has been considered to have impaired heat resistance and transparency is used, There is a possibility that the physical properties can be controlled only by changing to the partial structure of the invention. Furthermore, although it is a high molecular weight compound, since it has a low viscosity when dissolved in a solvent, it has excellent handling properties. And, since it can express a high refractive index with a polymer alone without containing a metal oxide, even when a dry process such as etching or ashing is performed, the etch rate becomes constant, and a film with a uniform film thickness can be obtained. Increases process margin when manufacturing devices.
- the physical properties of the triphenylamine ring-containing polymer and carbazole ring-containing polymer of the present invention can be controlled by changing the type of monomer that is a starting material at the time of synthesis.
- the phenylnaphthylamine-containing polymer of the present invention can be used as a high heat-resistant insulating material.
- Films prepared using the phenylnaphthylamine-containing polymer of the present invention having the above-mentioned characteristics such as high heat resistance, high transparency, high refractive index, high solubility, and low volume shrinkage are used for liquid crystal displays, organic electroluminescence. It can be suitably used as a member for producing electronic devices such as (EL) displays, optical semiconductor (LED) elements, solid-state imaging elements, organic thin film solar cells, dye-sensitized solar cells, and organic thin film transistors (TFTs).
- the present invention also relates to a composition of the polymer and other polymer (thermoplastic resin or thermoplastic resin composition) for use in these applications.
- 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, phenol resin, urea resin, melamine resin, Examples thereof include saturated 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.
- a 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.
- (meth) acrylate compounds 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 tri Oxyethyl (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, tri
- 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.
- a photo radical initiator examples include acetophenones, benzophenones, Michler's benzoylbenzoate, amyloxime ester, tetramethylthiuram monosulfide, and thioxanthones.
- photocleavable photoradical polymerization initiators are preferred.
- the photocleavable photoradical polymerization initiator is described in the latest UV curing technology (page 159, 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 Lucillin TPO, manufactured by UCB, 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.
- polymerization can use the solvent described in the said film formation composition.
- Synthesis example 1 In a 100 mL four-necked flask, N-phenyl-1-naphthylamine (8.00 g, 0.036 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), benzaldehyde (3.87 g, 0.036 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), para Toluenesulfonic acid monohydrate (0.727 g, 0.0036 mol, manufactured by Kanto Chemical Co., Inc.) was added, toluene (37.92 g, manufactured by Kanto Chemical Co., Ltd.) was added and stirred, and the temperature was raised to 110 ° C. The polymerization was started after dissolution. After 12 hours, the mixture was allowed to cool to 60 ° C.
- pNPNA-BA target polymer (formula (3-13)), hereinafter abbreviated as pNPNA-BA, 8.5 g Got.
- the weight average molecular weight Mw measured by polystyrene conversion of pNPNA-BA by GPC was 11000, and the polydispersity Mw / Mn was 7.3.
- the NMR spectrum of pNPNA-BA is shown in FIG.
- Synthesis example 2 In a 100 mL four-necked flask, N-phenyl-1-naphthylamine (10.00 g, 0.046 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 1-naphthaldehyde (7.12 g, 0.046 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) ), Paratoluenesulfonic acid monohydrate (0.908 g, 0.0046 mol, manufactured by Kanto Chemical Co., Inc.), and 1,4-dioxane (21.03 g, manufactured by Kanto Chemical Co., Inc.) were added and stirred. The temperature was raised to 110 ° C. and dissolved to initiate polymerization.
- pNPNA-NA 11.6 g Got The weight average molecular weight Mw measured in terms of polystyrene by GPC of pNPNA-NA was 1400, and the polydispersity Mw / Mn was 1.62.
- the NMR spectrum of pNPNA-NA is shown in FIG.
- Synthesis example 3 In a 100 mL four-necked flask, N-phenyl-1-naphthylamine (8.00 g, 0.036 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 9-anthracenecarboxaldehyde (7.52 g, 0.036 mol, Tokyo Chemical Industry Co., Ltd.) Product), paratoluenesulfonic acid monohydrate (0.727 g, 0.0036 mol, manufactured by Kanto Chemical Co., Inc.), and toluene (37.92 g, manufactured by Kanto Chemical Co., Ltd.) was added and stirred, and the temperature was 110 ° C. The temperature was raised to dissolution and polymerization was started.
- pNPNA-AA target polymer (formula (3-15)), hereinafter abbreviated as pNPNA-AA) 8.5 g Got.
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of pNPNA-AA was 1400, and the polydispersity Mw / Mn was 1.63.
- the NMR spectrum of pNPNA-AA is shown in FIG.
- Synthesis example 4 In a 100 mL four-neck flask, N-phenyl-1-naphthylamine (8.00 g, 0.036 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 1-pyrenecarboxaldehyde (8.39 g, 0.036 mol, Tokyo Chemical Industry Co., Ltd.) Product), p-toluenesulfonic acid monohydrate (0.727 g, 0.0036 mol, manufactured by Kanto Chemical Co., Inc.) and 1,4-dioxane (21.03 g, manufactured by Kanto Chemical Co., Inc.) were added and stirred. Then, the temperature was raised to 110 ° C. and dissolved to initiate polymerization.
- pNPNA-Py 8.4 g Got The weight average molecular weight Mw measured by GPC of pNPNA-Py in terms of polystyrene was 1000, and the polydispersity Mw / Mn was 1.62.
- the NMR spectrum of pNPNA-Py is shown in FIG.
- Synthesis example 5 In a 100 mL four-neck flask, N-phenyl-1-naphthylamine (6.56 g, 0.030 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), carbazole (5.00 g, 0.030 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 1 -Add naphthaldehyde (9.35 g, 0.060 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), paratoluenesulfonic acid monohydrate (1.19 g, 0.0060 mol, manufactured by Kanto Chemical Co., Ltd.), 4-Dioxane (51.57 g, manufactured by Kanto Chemical Co., Inc.) was charged and stirred, and the temperature was raised to 110 ° C.
- pNPNA-Cz-NA target polymer 8 .4 g
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of pNPNA-Cz-NA was 1400, and the polydispersity Mw / Mn was 1.37.
- Synthesis example 7 In a 100 mL four-necked flask, N-phenyl-1-naphthylamine (10.43 g, 0.048 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), triphenylamine (5.00 g, 0.020 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) 1-pyrenecarboxaldehyde (15.63 g, 0.068 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), paratoluenesulfonic acid monohydrate (1.35 g, 0.0068 mol, manufactured by Kanto Chemical Co., Inc.) 1,4-dioxane (75.62 g, manufactured by Kanto Chemical Co., Inc.) was charged and stirred, and the temperature was raised to 110 ° C.
- pNPA-TPA-Py target polymer 8 .4 g was obtained.
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of pNPNA-TPA-Py was 1400, and the polydispersity Mw / Mn was 1.39.
- Example 1 To 20 g of the resin obtained in Synthesis Example 1, 4.0 g of TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) as a cross-linking agent, 0.60 g of pyridinium paratoluenesulfonate as a catalyst, and MegaFac R- as a surfactant 30 (Dainippon Ink Chemical Co., Ltd., trade name) 0.06 g was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 2 To 20 g of the resin obtained in Synthesis Example 2, 4.0 g of TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) as a cross-linking agent, 0.60 g of pyridinium paratoluenesulfonate as a catalyst, and MegaFac R- as a surfactant 30 (Dainippon Ink Chemical Co., Ltd., trade name) 0.06 g was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- MegaFac R- as a surfactant 30
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 3 To 20 g of the resin obtained in Synthesis Example 3, 4.0 g of TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) as a cross-linking agent, 0.60 g of pyridinium paratoluenesulfonate as a catalyst, and Megafax R- as a surfactant 30 (Dainippon Ink Chemical Co., Ltd., trade name) 0.06 g was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- Megafax R- as a surfactant 30
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 4 To 20 g of the resin obtained in Synthesis Example 4, TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) 4.0 g as a crosslinking agent, 0.60 g of pyridinium p-toluenesulfonate as a catalyst, and MegaFac R- as a surfactant 30 (Dainippon Ink Chemical Co., Ltd., trade name) 0.06 g was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- MegaFac R- as a surfactant 30
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 5 To 20 g of the resin obtained in Synthesis Example 5, 4.0 g of TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) as a cross-linking agent, 0.60 g of pyridinium paratoluenesulfonate as a catalyst, and Megafax R- as a surfactant 30 (Dainippon Ink Chemical Co., Ltd., trade name) 0.06 g was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- Megafax R- as a surfactant 30
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 6 To 20 g of the resin obtained in Synthesis Example 6, 4.0 g of TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) as a cross-linking agent, 0.60 g of pyridinium p-toluenesulfonate as a catalyst, Megafac R-30 as a surfactant 0.06 g (trade name, manufactured by Dainippon Ink & Chemicals, Inc.) was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 7 To 20 g of the resin obtained in Synthesis Example 7, 4.0 g of TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) as a cross-linking agent, 0.60 g of pyridinium paratoluenesulfonate as a catalyst, and MegaFac R- as a surfactant 30 (Dainippon Ink Chemical Co., Ltd., trade name) 0.06 g was mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Comparative Example 1 20 g of a commercially available phenol novolac resin (novolak resin obtained using phenol and formaldehyde, weight average molecular weight Mw2000), TMOM-BP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) 4.0 g as a crosslinking agent, catalyst As a surfactant, 0.60 g of pyridinium p-toluenesulfonate and 0.06 g of MegaFac R-30 (trade name, manufactured by Dainippon Ink Chemical Co., Ltd.) as a surfactant were mixed and dissolved in 283.59 g of cyclohexanone to obtain a solution.
- phenol novolac resin novolak resin obtained using phenol and formaldehyde, weight average molecular weight Mw2000
- TMOM-BP trade name, manufactured by Honshu Chemical Industry Co., Ltd.
- catalyst 0.60 g of pyridinium p-toluenesulfonate and 0.06
- 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m 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, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- the resist underlayer film solutions prepared in Examples 1 to 7 were each applied onto a silicon wafer using a spin coater. Baking was performed on a hot plate at 240 ° C. for 1 minute or at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness: 0.25 ⁇ m). These resist underlayer films were measured for refractive index (n value) and optical extinction coefficient (also called k value and attenuation coefficient) at a wavelength of 248 nm and a wavelength of 193 nm using a spectroscopic ellipsometer. The results are shown in Table 1.
- the resist underlayer film forming composition solutions prepared in Examples 1 to 7 and Comparative Example 1 were each applied onto a silicon wafer using a spin coater.
- the resist underlayer film (film thickness: 0.25 ⁇ m) was formed by baking at 400 ° C. for 2 minutes on a hot plate.
- This resist underlayer film was immersed in a solvent used for the resist, for example, ethyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and cyclohexanone, and it was confirmed that the resist underlayer film was insoluble in the solvent.
- Example 1 when the etching rate of a resin film (film thickness: 0.25 ⁇ m) obtained by applying the resist underlayer film forming composition prepared in Comparative Example 1 and baking at 240 ° C. for 1 minute was set to 1.00 A comparison was made with the dry etching rates of the resist underlayer films of Examples 7 to 7 and Comparative Example 1. The results are shown in Table 2.
- the speed ratio is a dry etching speed ratio of (resist underlayer film) / (resin film of Comparative Example 1).
- the phenylnaphthylamine novolak resin of the present invention has a refractive index of 1.75 to 1.80 at a wavelength of 550 nm and a refractive index of 1.68 to 1.78 at a wavelength of 633 nm. It was found that the refractive index was high.
- the resist underlayer film material used in the lithography process by the multilayer film of the present invention is different from the conventional high etch rate antireflection film, and has a dry etching rate selection ratio close to or smaller than that of the photoresist, a semiconductor substrate Thus, it is possible to provide a resist underlayer film that has a lower dry etching rate selection ratio than the above and can also have an effect as an antireflection film. It was also found that the lower layer film material of the present invention has heat resistance capable of forming a hard mask on the upper layer by vapor deposition.
- the phenyl naphthylamine novolak resin of the present invention has excellent transparency and heat resistance in the visible range, a high refractive index, and excellent solubility in various solvents. It can be widely applied as an optical member, such as a TFT array flattening film, an overcoat such as a color filter, a spacer material, a light extraction improving film for an EL display, a light intake improving layer for an imaging element, a light extraction improving layer for an LED element.
- an optical member such as a TFT array flattening film, an overcoat such as a color filter, a spacer material, a light extraction improving film for an EL display, a light intake improving layer for an imaging element, a light extraction improving layer for an LED element.
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Abstract
Description
ポリビニルカルバゾールを用いたレジスト下層膜形成組成物が例示されている(特許文献1、特許文献2、及び特許文献3を参照)。
フルオレンフェノールノボラック樹脂を用いたレジスト下層膜形成組成物が開示されている(例えば、特許文献4参照)。
フルオレンナフトールノボラック樹脂を用いたレジスト下層膜形成組成物が開示されている(例えば、特許文献5参照)。
フルオレンフェノールとアリールアルキレンを繰り返し単位とする樹脂を含むレジスト下層膜形成組成物が開示されている(例えば、特許文献6、特許文献7参照)。
フェニルナフチルアミンとアセトアルデヒドを用いたノボラック樹脂が開示されている(特許文献8参照)。
また、フェニルナフチルアミン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用いた電子デバイスを提供する。
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より選択され、かつ、該アルキル基、該アルケニル基及びアリール基は、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よい有機基を表し、
R4は炭素原子数6乃至40のアリール基及び複素環基からなる群より選択され、かつ、該アリール基及び該複素環基は、ハロゲン基、ニトロ基、アミノ基、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、炭素原子数6乃至40のアリール基、ホルミル基、カルボキシル基、又はヒドロキシ基で置換されていてもよい有機基を表し、
R5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6乃至40のアリール基、及び複素環基からなる群より選択され、かつ、該アルキル基、該アリール基及び該複素環基は、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よい有機基を表し、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よい。n1及びn2はそれぞれ0乃至3の整数である。)で表される単位構造(A)を含むポリマー、
第2観点として、上記式(1)のR5が水素原子であり、R4が置換されていてもよいフェニル基、ナフチル基、アントリル基、又はピレニル基である第1観点に記載のポリマー、
第3観点として、上記式(1)のR3が水素原子又はフェニル基である第1観点又は第2観点に記載のポリマー、
第4観点として、上記単位構造(A)においてAr1とAr2は、いずれか一方がベンゼン環であり他方がナフタレン環である単位構造(a1)を含む第1観点乃至第3観点のいずれか一つに記載のポリマー、
第5観点として、上記単位構造(A)においてAr1とAr2は、共にベンゼン環となる単位構造(a2)を含む第1観点乃至第3観点のいずれか一つに記載のポリマー、
第6観点として、第4観点に記載の単位構造(a1)と第5観点に記載の単位構造(a2)を含む共重合体であるポリマー、
第7観点として、第1観点に記載の式(1)の単位構造(A)と下記式(2)の単位構造(B):
第8観点として、第4観点に記載の単位構造(a1)と第7観点に記載の単位構造(B)を含む共重合体であるポリマー、
第9観点として、第1観点乃至第8観点のいずれか一つに記載のポリマーを含むリソグラフィー用レジスト下層膜形成組成物、
第10観点として、更に架橋剤を含む第9観点に記載のレジスト下層膜形成組成物、
第11観点として、更に酸及び/又は酸発生剤を含む第9観点又は第10観点に記載のレジスト下層膜形成組成物、
第12観点として、第9観点乃至第11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得られるレジスト下層膜、
第13観点として、半導体基板上に第9観点乃至第11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下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像により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より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により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、及び、
第14観点として、半導体基板に第9観点乃至第11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下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像により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より該ハードマスクをエッチングする工程、パターン化された該ハードマスクにより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により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である。
本発明のレジスト下層膜形成組成物には基板からの反射を効率的に抑制する性能を付与することも可能であり、露光光の反射防止膜としての効果を併せ持つこともできる。
本発明のレジスト下層膜形成組成物により、レジストに近いドライエッチング速度の選択比、レジストに比べて小さいドライエッチング速度の選択比や半導体基板に比べて小さいドライエッチング速度の選択比を持つ、優れたレジスト下層膜を提供することができる。
本発明に用いられるポリマーは、重量平均分子量が600乃至1000000、又は600乃至200000である。
本発明に用いられるポリマーは式(1)で示される繰り返し単位構造(A)を含む。
式(1)中、Ar1、及びAr2はそれぞれベンゼン環、ナフタレン環を示し、R1及びR2はそれぞれこれら環上の水素原子の置換基でありハロゲン基、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、該アルケニル基及び該アリール基は、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よい有機基を表し、
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、該アルケニル基及び該アリール基は、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よい有機基を表し、
R4は炭素原子数6乃至40のアリール基及び複素環基からなる群より選択され、かつ、該アリール基及び該複素環基は、ハロゲン基、ニトロ基、アミノ基、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、炭素原子数6乃至40のアリール基、ホルミル基、カルボキシル基、又はヒドロキシ基で置換されていてもよい有機基を表し、
R5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6乃至40のアリール基、及び複素環基からなる群より選択され、かつ、該アルキル基、該アリール基及び該複素環基は、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よい有機基であり、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よい。n1及びn2はそれぞれ0乃至3の整数である。
炭素原子数1乃至10のアルキル基としてはメチル基、エチル基、n-プロピル基、i-プロピル基、シクロプロピル基、n-ブチル基、i-ブチル基、s-ブチル基、t-ブチル基、シクロブチル基、1-メチル-シクロプロピル基、2-メチル-シクロプロピル基、n-ペンチル基、1-メチル-n-ブチル基、2-メチル-n-ブチル基、3-メチル-n-ブチル基、1,1-ジメチル-n-プロピル基、1,2-ジメチル-n-プロピル基、2,2-ジメチル-n-プロピル基、1-エチル-n-プロピル基、シクロペンチル基、1-メチル-シクロブチル基、2-メチル-シクロブチル基、3-メチル-シクロブチル基、1,2-ジメチル-シクロプロピル基、2,3-ジメチル-シクロプロピル基、1-エチル-シクロプロピル基、2-エチル-シクロプロピル基、n-ヘキシル基、1-メチル-n-ペンチル基、2-メチル-n-ペンチル基、3-メチル-n-ペンチル基、4-メチル-n-ペンチル基、1,1-ジメチル-n-ブチル基、1,2-ジメチル-n-ブチル基、1,3-ジメチル-n-ブチル基、2,2-ジメチル-n-ブチル基、2,3-ジメチル-n-ブチル基、3,3-ジメチル-n-ブチル基、1-エチル-n-ブチル基、2-エチル-n-ブチル基、1,1,2-トリメチル-n-プロピル基、1,2,2-トリメチル-n-プロピル基、1-エチル-1-メチル-n-プロピル基、1-エチル-2-メチル-n-プロピル基、シクロヘキシル基、1-メチル-シクロペンチル基、2-メチル-シクロペンチル基、3-メチル-シクロペンチル基、1-エチル-シクロブチル基、2-エチル-シクロブチル基、3-エチル-シクロブチル基、1,2-ジメチル-シクロブチル基、1,3-ジメチル-シクロブチル基、2,2-ジメチル-シクロブチル基、2,3-ジメチル-シクロブチル基、2,4-ジメチル-シクロブチル基、3,3-ジメチル-シクロブチル基、1-n-プロピル-シクロプロピル基、2-n-プロピル-シクロプロピル基、1-i-プロピル-シクロプロピル基、2-i-プロピル-シクロプロピル基、1,2,2-トリメチル-シクロプロピル基、1,2,3-トリメチル-シクロプロピル基、2,2,3-トリメチル-シクロプロピル基、1-エチル-2-メチル-シクロプロピル基、2-エチル-1-メチル-シクロプロピル基、2-エチル-2-メチル-シクロプロピル基及び2-エチル-3-メチル-シクロプロピル基等が挙げられる。
なかでも高屈折率材料に用いるためにはイオウを含む複素環基が好ましい。
また、上記式(1)で表される単位構造(A)はR3が水素原子又はフェニル基とすることができる。
本発明では上記単位構造(A)においてAr1とAr2は、いずれか一方がベンゼン環であり他方がナフタレン環である単位構造(a1)を用いることができる。また、上記単位構造(A)においてAr1とAr2は、共にベンゼン環となる単位構造(a2)を用いることができる。
そして式(1)で示される単位構造(A)と式(2)で示される単位構造(B)を含む共重合体とすることができる。
これらの置換基やアルキル基、アリール基、複素環基は上述の例示を用いることができる。
本発明のポリマーは、上記単位構造(a1)と上記単位構造(B)を含む共重合体とすることができる。
この縮合反応ではジアリールアミン等のアミン類のフェニル基1当量に対して、アルデヒド類又はケトン類を0.1乃至10当量の割合で用いることができる。
以上のようにして得られる重合体の重量平均分子量Mwは、通常600乃至1000000、又は600乃至200000である。
本発明においてリソグラフィー用レジスト下層膜形成組成物は上記ポリマーと溶剤を含む。そして、架橋剤と酸を含むことができ、必要に応じて酸発生剤、界面活性剤等の添加剤を含むことができる。この組成物の固形分は0.1乃至70質量%、または0.1乃至60質量%である。固形分はレジスト下層膜形成組成物から溶剤を除いた全成分の含有割合である。固形分中に上記ポリマーを1乃至100質量%、または1乃至99.9質量%、または50乃至99.9質量%の割合で含有することができる。
それらポリマーとしてはポリアクリル酸エステル化合物、ポリメタクリル酸エステル化合物、ポリアクリルアミド化合物、ポリメタクリルアミド化合物、ポリビニル化合物、ポリスチレン化合物、ポリマレイミド化合物、ポリマレイン酸無水物、及びポリアクリロニトリル化合物が挙げられる。
アクリルアミド化合物としては、アクリルアミド、N-メチルアクリルアミド、N-エチルアクリルアミド、N-ベンジルアクリルアミド、N-フェニルアクリルアミド、及びN,N-ジメチルアクリルアミド等が挙げられる。
この化合物は下記式(4)の部分構造を有する化合物や、下記式(5)の繰り返し単位を有するポリマー又はオリゴマーが挙げられる。
これらのアルキル基及びアリール基は、上記アルキル基及びアリール基を例示することができる。
架橋剤の添加量は、使用する塗布溶剤、使用する下地基板、要求される溶液粘度、要求される膜形状などにより変動するが、全固形分に対して0.001乃至80質量%、好ましくは 0.01乃至50質量%、さらに好ましくは0.05乃至40質量%である。これら架橋剤は自己縮合による架橋反応を起こすこともあるが、本発明の上記のポリマー中に架橋性置換基が存在する場合は、それらの架橋性置換基と架橋反応を起こすことができる。
本発明におけるリソグラフィー用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、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あり、例えば、ロームアンドハーツ社製、商品名APEX-Eが挙げられる。
また電子線レジストの電子線照射は、例えば電子線照射装置を用い照射することができる。
即ち、半導体基板にレジスト下層膜形成組成物により該レジスト下層膜を形成する工程、その上にケイ素成分等を含有する塗膜材料によるハードマスク又は蒸着によるハードマスク(例えば、窒化酸化ケイ素)を形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、レジストパターンによりハードマスクをハロゲン系ガスでエッチングする工程、パターン化されたハードマスクにより該レジスト下層膜を酸素系ガス又は水素系ガスで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によりハロゲン系ガスで半導体基板を加工する工程を経て半導体装置を製造することができる。
即ち、上記式(1)で示される単位構造を含むポリマー(例えばフェニルナフチルアミンノボラック樹脂)を含む高屈折率膜形成組成物を得ることができる。そして上記高屈折率膜形成組成物を塗布して高屈折率膜が得られ、それらの高屈折率膜を含む電子デバイスを得ることができる。この用途に用いられるポリマーの重量平均分子量は1000乃至2000000である高分岐ポリマー又はリニアポリマーである。
上記固形分中に上記ポリマー(例えばフェニルナフチルアミンノボラック樹脂)を1乃至100質量%、または1乃至99.9質量%、または50乃至99.9質量%の割合で含有することができる。本発明の効果を損なわない限りにおいて、ポリマーおよび溶剤以外のその他の成分、例えば上記レベリング剤、界面活性剤、架橋剤等が含まれていてもよい。
さらに、高分子量の化合物であるにもかかわらず、溶剤に溶解したときに低粘度であるため、ハンドリング性に優れる。
そして、金属酸化物を含まず、ポリマー単独で高屈折率を発現できることから、エッチングやアッシングなどのドライプロセスを経る場合でも、エッチレートが一定となり、均一な膜厚の被膜を得ることができ、デバイスを作製する際のプロセスマージンが拡大する。
また、本発明のトリフェニルアミン環含有ポリマーおよびカルバゾール環含有ポリマーは、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。
また、本発明のフェニルナフチルアミン含有ポリマーは高耐熱性絶縁材料として使用できる。
本発明は、それら用途に利用するための前記ポリマーと他のポリマー(熱可塑性樹脂または熱可塑性樹脂組成物)との組成物にも関する。
(メタ)アクリレート化合物の例としては、メチル(メタ)アクリレート、エチル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、1,4-ブタンジオールジ(メタ)アクリレート、1,6-ヘキサンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリメチロールプロパントリオキシエチル(メタ)アクリレート、トリシクロデカンジメタノールジ(メタ)アクリレート、トリシクロデカニルジ(メタ)アクリレート、トリメチロールプロパントリオキシプロピル(メタ)アクリレート、トリス-2-ヒドロキシエチルイソシアヌレートトリ(メタ)アクリレート、トリス-2-ヒドロキシエチルイソシアヌレートジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、グリセリンメタクリレートアクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリメチロールプロパントリメタクリレート、(メタ)アクリル酸アリル、(メタ)アクリル酸ビニル、エポキシ(メタ)アクリレート、ポリエステル(メタ)アクリレートおよびウレタン(メタ)アクリレート等が挙げられる。
光ラジカル重合開始剤としては、例えば、アセトフェノン類、ベンゾフェノン類、ミヒラーのベンゾイルベンゾエート、アミロキシムエステル、テトラメチルチウラムモノサルファイドおよびチオキサントン類等が挙げられる。
特に、光開裂型の光ラジカル重合開始剤が好ましい。光開裂型の光ラジカル重合開始剤については、最新UV硬化技術(159頁、(株)技術情報協会、1991年発行)に記載されている。
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。
重合時に用いる溶剤は、前記膜形成用組成物に記載した溶剤を用いることができる。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(8.00g、0.036mol、東京化成工業(株)製)、ベンズアルデヒド(3.87g、0.036mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.727g、0.0036mol、関東化学(株)製)を加え、トルエン(37.92g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後60℃まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-13))、以下pNPNA-BAと略す)8.5gを得た。
pNPNA-BA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11000、多分散度Mw/Mnは7.3であった。そして、pNPNA-BAのNMRスペクトルを図1に示した。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(10.00g、0.046mol、東京化成工業(株)製)、1-ナフトアルデヒド(7.12g、0.046mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.908g、0.0046mol、関東化学(株)製)を加え、1,4-ジオキサン(21.03g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後室温まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-14))、以下pNPNA-NAと略す)11.6gを得た。
pNPNA-NA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1400、多分散度Mw/Mnは1.62であった。そして、pNPNA-NAのNMRスペクトルを図2に示した。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(8.00g、0.036mol、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(7.52g、0.036mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.727g、0.0036mol、関東化学(株)製)を加え、トルエン(37.92g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後60℃まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-15))、以下pNPNA-AAと略す)8.5gを得た。
pNPNA-AA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1400、多分散度Mw/Mnは1.63であった。そして、pNPNA-AAのNMRスペクトルを図3に示した。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(8.00g、0.036mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(8.39g、0.036mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.727g、0.0036mol、関東化学(株)製)を加え、1,4-ジオキサン(21.03g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後室温まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-16))、以下pNPNA-Pyと略す)8.4gを得た。
pNPNA-Py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1000、多分散度Mw/Mnは1.62であった。そして、pNPNA-PyのNMRスペクトルを図4に示した。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(6.56g、0.030mol、東京化成工業(株)製)、カルバゾール(5.00g、0.030mol、東京化成工業(株)製)、1-ナフトアルデヒド(9.35g、0.060mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.19g、0.0060mol、関東化学(株)製)を加え、1,4-ジオキサン(51.57g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後室温まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-19))、以下pNPNA-Cz-NAと略す)8.4gを得た。
pNPNA-Cz-NA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1400、多分散度Mw/Mnは1.37であった。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(6.56g、0.030mol、東京化成工業(株)製)、カルバゾール(5.00g、0.030mol、東京化成工業(株)製)、1-ナフトアルデヒド(4.67g、0.030mol、東京化成工業(株)製)、4-メチルベンズアルデヒド(3.60g、0.030mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.19g、0.0060mol、関東化学(株)製)を加え、1,4-ジオキサン(49.02g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後室温まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-21))、以下pNPNA-Cz-NA-MBAと略す)8.4gを得た。
pNPNA-Cz-NA-MBA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1400、多分散度Mw/Mnは1.37であった。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(10.43g、0.048mol、東京化成工業(株)製)、トリフェニルアミン(5.00g、0.020mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(15.63g、0.068mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(1.35g、0.0068mol、関東化学(株)製)を加え、1,4-ジオキサン(75.62g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後室温まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(3-20))、以下pNPA-TPA-Pyと略す)8.4gを得た。
pNPNA-TPA-Py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1400、多分散度Mw/Mnは1.39であった。
合成例1で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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5で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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6で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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7で得た樹脂20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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。
市販のフェノールノボラック樹脂(フェノ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、重量平均分子量はMw2000)20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、商品名)4.0g、触媒としてピリジニウムパラトルエンスルホネート0.60g、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、シクロヘキサノン283.59gに溶解させ溶液とした。その後、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。
実施例1乃至7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た。ホットプレート上で240℃1分間、または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7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た。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。このレジスト下層膜をレジストに使用する溶剤、例えば乳酸エチル、ならびに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、シクロヘキサノンに浸漬し、その溶剤に不溶であることを確認した。
ドライエッチング速度の測定に用いたエッチャ-及びエッチングガスは以下のものを用いた。
ES401(日本サイエンティフィック製):CF4
実施例1乃至7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た。ホットプレート上で240℃1分間、または400℃2分間焼成し、レジスト下層膜(膜厚0.25μm)を形成した。エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定した。
比較例1で調製されたレジスト下層膜形成組成物を塗布し、240℃1分間焼成して得られた樹脂膜(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7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。速度比は(レジスト下層膜)/(比較例1の樹脂膜)のドライエッチング速度比である。
実施例1乃至7で得られたノボラック樹脂薄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3に示す。
また本発明のフェニルナフチルアミンノボラック樹脂は、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、広く光学部材として応用可能である。
Claims (14)
- 下記式(1):
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、該アルケニル基及びアリール基は、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よい有機基を表し、
R4は炭素原子数6乃至40のアリール基及び複素環基からなる群より選択され、かつ、該アリール基及び該複素環基は、ハロゲン基、ニトロ基、アミノ基、炭素原子数1乃至10のアルキル基、炭素原子数1乃至10のアルコキシ基、炭素原子数6乃至40のアリール基、ホルミル基、カルボキシル基、又は水酸基で置換されていてもよい有機基を表し、
R5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6乃至40のアリール基、及び複素環基からなる群より選択され、かつ、該アルキル基、該アリール基及び該複素環基は、ハロゲン基、ニトロ基、アミノ基、若しくは水酸基で置換されていてもよい有機基を表し、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よい。n1及びn2はそれぞれ0乃至3の整数である。)で表される単位構造(A)を含むポリマー。 - 上記式(1)のR5が水素原子であり、R4が置換されていてもよいフェニル基、ナフチル基、アントリル基、又はピレニル基である請求項1に記載のポリマー。
- 上記式(1)のR3が水素原子又はフェニル基である請求項1又は請求項2に記載のポリマー。
- 上記単位構造(A)においてAr1とAr2は、いずれか一方がベンゼン環であり他方がナフタレン環である単位構造(a1)を含む請求項1乃至請求項3のいずれか1項に記載のポリマー。
- 上記単位構造(A)においてAr1とAr2は、共にベンゼン環となる単位構造(a2)を含む請求項1乃至請求項3のいずれか1項に記載のポリマー。
- 請求項4に記載の単位構造(a1)と請求項5に記載の単位構造(a2)を含む共重合体であるポリマー。
- 請求項1に記載の式(1)の単位構造(A)と下記式(2)の単位構造(B):
- 請求項4に記載の単位構造(a1)と請求項7に記載の単位構造(B)を含む共重合体であるポリマー。
- 請求項1乃至請求項8のいずれか1項に記載のポリマーを含むリソグラフィー用レジスト下層膜形成組成物。
- 更に架橋剤を含む請求項9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9又は請求項10に記載のレジスト下層膜形成組成物。
- 請求項9乃至請求項11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得られるレジスト下層膜。
- 半導体基板上に請求項9乃至請求項11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下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像により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より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により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。
- 半導体基板に請求項9乃至請求項11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下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像により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より該ハードマスクをエッチングする工程、パターン化された該ハードマスクにより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により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。
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US14/348,461 US9263286B2 (en) | 2011-09-29 | 2012-09-25 | Diarylamine novolac resin |
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Also Published As
Publication number | Publication date |
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CN103827159A (zh) | 2014-05-28 |
KR20140069163A (ko) | 2014-06-09 |
JPWO2013047516A1 (ja) | 2015-03-26 |
US9263286B2 (en) | 2016-02-16 |
TWI610955B (zh) | 2018-01-11 |
US20140235059A1 (en) | 2014-08-21 |
TW201333057A (zh) | 2013-08-16 |
KR101989313B1 (ko) | 2019-06-14 |
CN103827159B (zh) | 2016-07-06 |
JP6066092B2 (ja) | 2017-01-25 |
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