JP4651283B2 - 不飽和カルボン酸ヘミアセタールエステル、高分子化合物及びフォトレジスト用樹脂組成物 - Google Patents
不飽和カルボン酸ヘミアセタールエステル、高分子化合物及びフォトレジスト用樹脂組成物 Download PDFInfo
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- JP4651283B2 JP4651283B2 JP2004028595A JP2004028595A JP4651283B2 JP 4651283 B2 JP4651283 B2 JP 4651283B2 JP 2004028595 A JP2004028595 A JP 2004028595A JP 2004028595 A JP2004028595 A JP 2004028595A JP 4651283 B2 JP4651283 B2 JP 4651283B2
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- -1 carboxylic acid hemiacetal ester Chemical class 0.000 title claims description 94
- 150000001875 compounds Chemical class 0.000 title claims description 73
- 229920000642 polymer Polymers 0.000 title claims description 50
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 26
- 239000011342 resin composition Substances 0.000 title claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 77
- 239000000178 monomer Substances 0.000 claims description 62
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 150000002430 hydrocarbons Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 239000004065 semiconductor Substances 0.000 claims description 11
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 44
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- PHPRWKJDGHSJMI-UHFFFAOYSA-N 1-adamantyl prop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C=C)C3 PHPRWKJDGHSJMI-UHFFFAOYSA-N 0.000 description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 125000006841 cyclic skeleton Chemical group 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004018 acid anhydride group Chemical group 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000003997 cyclic ketones Chemical group 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000005462 imide group Chemical group 0.000 description 4
- 150000002596 lactones Chemical group 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 description 4
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001226 reprecipitation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical group CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 4
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 0 C*C(C)(C)C(OC1(CC2CC(C3)C1)CC3OC2=O)=O Chemical compound C*C(C)(C)C(OC1(CC2CC(C3)C1)CC3OC2=O)=O 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YCEXJLPTIKPSSG-UHFFFAOYSA-N O1C(=O)C(C2)CC3(OC(=O)C(=C)C)CC1CC2C3 Chemical compound O1C(=O)C(C2)CC3(OC(=O)C(=C)C)CC1CC2C3 YCEXJLPTIKPSSG-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 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
- 239000007877 V-601 Substances 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 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
- MWMWRSCIFDZZGW-UHFFFAOYSA-N (2-oxooxolan-3-yl) prop-2-enoate Chemical compound C=CC(=O)OC1CCOC1=O MWMWRSCIFDZZGW-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- GVJFFQYXVOJXFI-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a,9,9a,10,10a-tetradecahydroanthracene Chemical group C1C2CCCCC2CC2C1CCCC2 GVJFFQYXVOJXFI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AQWFAJNYMNVUBG-UHFFFAOYSA-N 1-(2-ethenoxyethyl)adamantane Chemical compound C1C(C2)CC3CC2CC1(CCOC=C)C3 AQWFAJNYMNVUBG-UHFFFAOYSA-N 0.000 description 2
- SORYNAJJYBJNMX-UHFFFAOYSA-N 1-[(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)oxy]ethyl 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(C)OC(=O)C(C)=C)CC1C2(C)C SORYNAJJYBJNMX-UHFFFAOYSA-N 0.000 description 2
- OLWAZOBRCQWWDB-UHFFFAOYSA-N 2,3,4,4a,4b,5,6,7,8,8a,9,9a-dodecahydro-1h-fluorene Chemical group C12CCCCC2CC2C1CCCC2 OLWAZOBRCQWWDB-UHFFFAOYSA-N 0.000 description 2
- LQLLNKLOYCYFEB-UHFFFAOYSA-N 3-ethenoxy-4,7,7-trimethylbicyclo[2.2.1]heptane Chemical compound C1CC2(C)C(OC=C)CC1C2(C)C LQLLNKLOYCYFEB-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VYIMKCXVRQCRFJ-UHFFFAOYSA-N C1OC(=O)C2C1C1(OC(=O)C=C)CC2CC1 Chemical compound C1OC(=O)C2C1C1(OC(=O)C=C)CC2CC1 VYIMKCXVRQCRFJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane group Chemical group C12(CCC(CC1)C2(C)C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical group C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical group C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 2
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- CMUWMQXDTPDEDU-UHFFFAOYSA-N tert-butyl 5-oxo-1-prop-2-enoyloxy-4-oxatricyclo[4.2.1.03,7]nonane-9-carboxylate Chemical compound C(C=C)(=O)OC12CC3OC(C(C3C1)C2C(=O)OC(C)(C)C)=O CMUWMQXDTPDEDU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
で表される不飽和カルボン酸ヘミアセタールエステルを提供する。
で表される繰り返し単位を含む高分子化合物を提供する。
で表される単量体、無水マレイン酸、マレイミドから選択された少なくとも1種の単量体に対応する繰り返し単位を含んでいてもよい。
なお、本明細書では、上記の発明のほか、下記式(1)
で表される不飽和カルボン酸ヘミアセタールエステル、及び下記式(I)
で表される繰り返し単位を含む高分子化合物についても説明する。
本発明の不飽和カルボン酸ヘミアセタールエステルは、前記式(1)で表される。式(1)中、Raは水素原子、ハロゲン原子、炭素数1〜6のアルキル基又は炭素数1〜6のハロアルキル基を示し、Rbは1位に水素原子を有する炭化水素基を示し、Rcは水素原子又は炭化水素基を示し、Rdは環式骨格を含む有機基を示す。
[1-1]1−(アダマンタン−1−イルオキシ)エチル(メタ)アクリレート
[1-2]1−(アダマンタン−1−イルメトキシ)エチル(メタ)アクリレート
[1-3]1−[2−(アダマンタン−1−イル)エトキシ]エチル(メタ)アクリレート
[1-4]1−[1−(アダマンタン−1−イル)−1−メチルエトキシ]エチル(メタ)アクリレート
[1-5]1−(2−メチルアダマンタン−2−イルオキシ)エチル(メタ)アクリレート
[1-6]1−(3−ヒドロキシアダマンタン−1−イルオキシ)エチル(メタ)アクリレート
[1-7]1−(3,5−ジヒドロキシアダマンタン−1−イルオキシ)エチル(メタ)アクリレート
[1-8]1−(3−カルボキシアダマンタン−1−イルオキシ)エチル(メタ)アクリレート
[1-9]1−(3,5−ジカルボキシアダマンタン−1−イルオキシ)エチル(メタ)アクリレート
[1-10]1−(ノルボルナン−2−イルオキシ)エチル(メタ)アクリレート
[1-11]1−(ノルボルナン−2−イルメトキシ)エチル(メタ)アクリレート
[1-12]1−(2−メチルノルボルナン−2−イルオキシ)エチル(メタ)アクリレート
[1-13]1−[1−(ノルボルナン−2−イル)−1−メチルエトキシ]エチル(メタ)アクリレート
[1-14]1−(3−ヒドロキシノルボルナン−2−イルオキシ)エチル(メタ)アクリレート
[1-15]1−(3−ヒドロキシメチルノルボルナン−2−イルメトキシ)エチル(メタ)アクリレート
[1-16]1−(5,6−ジヒドロキシノルボルナン−2−イルメトキシ)エチル(メタ)アクリレート
[1-17]1−(3−メチルノルボルナン−2−イルメトキシ)エチル(メタ)アクリレート
[1-18]1−(デカリン−1−イルオキシ)エチル(メタ)アクリレート
[1-19]1−(デカリン−2−イルオキシ)エチル(メタ)アクリレート
[1-20]1−(5−ヒドロキシデカリン−1−イルオキシ)エチル(メタ)アクリレート
[1-21]8−ヒドロキシメチル−4−[1−(メタ)アクリロイルオキシエトキシメチル]トリシクロ[5.2.1.02,6]デカン
[1-22]4−ヒドロキシメチル−8−[1−(メタ)アクリロイルオキシエトキシメチル]トリシクロ[5.2.1.02,6]デカン
[1-23]1−(ボルニルオキシ)エチル(メタ)アクリレート
[1-24]1−(イソボルニルオキシ)エチル(メタ)アクリレート
[1-25]3−カルボキシ−8−[1−(メタ)アクリロイルオキシエトキシ]テトラシクロ[4.4.0.12,5.17,10]ドデカン
[1-26]3−カルボキシ−9−[1−(メタ)アクリロイルオキシエトキシ]テトラシクロ[4.4.0.12,5.17,10]ドデカン
本発明の高分子化合物は、上記不飽和カルボン酸ヘミアセタールエステルに対応する繰り返し単位(モノマー単位)、すなわち式(I)で表される単位を含んでいる。該繰り返し単位は1種であってもよく2種以上であってもよい。このような高分子化合物は、上記不飽和カルボン酸ヘミアセタールエステルを重合に付すことにより得ることができる。
[2-1]1−(メタ)アクリロイルオキシ−4−オキソアダマンタン(R=H又はCH3、R1=R2=R3=H、V1=−CO−、V2=V3=−CH2−)
[2-2]1−(メタ)アクリロイルオキシ−4−オキサトリシクロ[4.3.1.13,8]ウンデカン−5−オン(R=H又はCH3、R1=R2=R3=H、V2=−CO−O−(左側がR2の結合している炭素原子側)、V1=V3=−CH2−)
[2-3]1−(メタ)アクリロイルオキシ−4,7−ジオキサトリシクロ[4.4.1.13,9]ドデカン−5,8−ジオン(R=H又はCH3、R1=R2=R3=H、V1=−CO−O−(左側がR1の結合している炭素原子側)、V2=−CO−O−(左側がR2の結合している炭素原子側)、V3=−CH2−)
[2-4]1−(メタ)アクリロイルオキシ−4,8−ジオキサトリシクロ[4.4.1.13,9]ドデカン−5,7−ジオン(R=H又はCH3、R1=R2=R3=H、V1=−O−CO−(左側がR1の結合している炭素原子側)、V2=−CO−O−(左側がR2の結合している炭素原子側)、V3=−CH2−)
[2-5]1−(メタ)アクリロイルオキシ−5,7−ジオキサトリシクロ[4.4.1.13,9]ドデカン−4,8−ジオン(R=H又はCH3、R1=R2=R3=H、V1=−CO−O−(左側がR1の結合している炭素原子側)、V2=−O−CO−(左側がR2の結合している炭素原子側)、V3=−CH2−)
[2-6]2−(メタ)アクリロイルオキシ−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(=5−(メタ)アクリロイルオキシ−2,6−ノルボルナンカルボラクトン)(R=H又はCH3、R4=R5=R6=H、X=メチレン基)
[2-7]2−(メタ)アクリロイルオキシ−2−メチル−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R4=CH3、R5=R6=H、X=メチレン基)
[2-8]2−(メタ)アクリロイルオキシ−6−メチル−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R5=CH3、R4=R6=H、X=メチレン基)
[2-9]2−(メタ)アクリロイルオキシ−9−メチル−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R6=CH3、R4=R5=H、X=メチレン基)
[2-10]2−(メタ)アクリロイルオキシ−9−カルボキシ−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R4=R5=H、R6=COOH、X=メチレン基)
[2-11]2−(メタ)アクリロイルオキシ−9−メトキシカルボニル−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R4=R5=H、R6=メトキシカルボニル基、X=メチレン基)
[2-12]2−(メタ)アクリロイルオキシ−9−エトキシカルボニル−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R4=R5=H、R6=エトキシカルボニル基、X=メチレン基)
[2-13]2−(メタ)アクリロイルオキシ−9−t−ブトキシカルボニル−4−オキサトリシクロ[4.2.1.03,7]ノナン−5−オン(R=H又はCH3、R4=R5=H、R6=t−ブトキシカルボニル基、X=メチレン基)
[2-14]8−(メタ)アクリロイルオキシ−4−オキサトリシクロ[5.2.1.02,6]デカン−5−オン(R=H又はCH3)
[2-15]9−(メタ)アクリロイルオキシ−4−オキサトリシクロ[5.2.1.02,6]デカン−5−オン(R=H又はCH3)
[2-16]4−(メタ)アクリロイルオキシ−6−オキサビシクロ[3.2.1]オクタン−7−オン(R=H又はCH3、R9=R10=R11=R12=R13=R14=R15=R16=R17=H)
[2-17]4−(メタ)アクリロイルオキシ−4−メチル−6−オキサビシクロ[3.2.1]オクタン−7−オン(R=H又はCH3、R10=R11=R12=R13=R14=R15=R16=R17=H、R9=CH3)
[2-18]4−(メタ)アクリロイルオキシ−5−メチル−6−オキサビシクロ[3.2.1]オクタン−7−オン(R=H又はCH3、R9=R11=R12=R13=R14=R15=R16=R17=H、R10=CH3)
[2-19]4−(メタ)アクリロイルオキシ−4,5−ジメチル−6−オキサビシクロ[3.2.1]オクタン−7−オン(R=H又はCH3、R11=R12=R13=R14=R15=R16=R17=H、R9=R10=CH3)
[2-20]6−(メタ)アクリロイルオキシ−2−オキサビシクロ[2.2.2]オクタン−3−オン(R=H又はCH3、R18=R19=R20=R21=R22=R23=R24=R25=R26=H)
[2-21]6−(メタ)アクリロイルオキシ−6−メチル−2−オキサビシクロ[2.2.2]オクタン−3−オン(R=H又はCH3、R18=R20=R21=R22=R23=R24=R25=R26=H、R19=CH3)
[2-22]6−(メタ)アクリロイルオキシ−1−メチル−2−オキサビシクロ[2.2.2]オクタン−3−オン(R=H又はCH3、R19=R20=R21=R22=R23=R24=R25=R26=H、R18=CH3)
[2-23]6−(メタ)アクリロイルオキシ−1,6−ジメチル−2−オキサビシクロ[2.2.2]オクタン−3−オン(R=H又はCH3、R20=R21=R22=R23=R24=R25=R26=H、R18=R19=CH3)
[2-24]β−(メタ)アクリロイルオキシ−γ−ブチロラクトン(R=H又はCH3、R27=R28=R29=R30=R31=H)
[2-25]β−(メタ)アクリロイルオキシ−α,α−ジメチル−γ−ブチロラクトン(R=H又はCH3、R27=R28=CH3、R29=R30=R31=H)
[2-26]β−(メタ)アクリロイルオキシ−γ,γ−ジメチル−γ−ブチロラクトン(R=H又はCH3、R30=R31=CH3、R27=R28=R29=H)
[2-27]β−(メタ)アクリロイルオキシ−α,α,β−トリメチル−γ−ブチロラクトン(R=H又はCH3、R27=R28=R29=CH3、R30=R31=H)
[2-28]β−(メタ)アクリロイルオキシ−β,γ,γ−トリメチル−γ−ブチロラクトン(R=H又はCH3、R29=R30=R31=CH3、R27=R28=H)
[2-29]β−(メタ)アクリロイルオキシ−α,α,β,γ,γ−ペンタメチル−γ−ブチロラクトン(R=H又はCH3、R27=R28=R29=R30=R31=CH3)
[2-30]α−(メタ)アクリロイルオキシ−γ−ブチロラクトン(R=H又はCH3、R32=R33=R34=R35=R36=H)
[2-31]α−(メタ)アクリロイルオキシ−α−メチル−γ−ブチロラクトン(R=H又はCH3、R32=CH3、R33=R34=R35=R36=H)
[2-32]α−(メタ)アクリロイルオキシ−β,β−ジメチル−γ−ブチロラクトン(R=H又はCH3、R33=R34=CH3、R32=R35=R36=H)
[2-33]α−(メタ)アクリロイルオキシ−α,β,β−トリメチル−γ−ブチロラクトン(R=H又はCH3、R32=R33=R34=CH3、R35=R36=H)
[2-34]α−(メタ)アクリロイルオキシ−γ,γ−ジメチル−γ−ブチロラクトン(R=H又はCH3、R35=R36=CH3、R32=R33=R34=H)
[2-35]α−(メタ)アクリロイルオキシ−α,γ,γ−トリメチル−γ−ブチロラクトン(R=H又はCH3、R32=R35=R36=CH3、R33=R34=H)
[2-36]α−(メタ)アクリロイルオキシ−β,β,γ,γ−テトラメチル−γ−ブチロラクトン(R=H又はCH3、R33=R34=R35=R36=CH3、R32=H)
[2-37]α−(メタ)アクリロイルオキシ−α,β,β,γ,γ−ペンタメチル−γ−ブチロラクトン(R=H又はCH3、R32=R33=R34=R35=R36=CH3)
[3-1]1−ヒドロキシ−3−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=OH、n=1、Z2=アダマンタン環)
[3-2]1,3−ジヒドロキシ−5−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=OH、n=2、Z2=アダマンタン環)
[3-3]1−カルボキシ−3−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=COOH、n=1、Z2=アダマンタン環)
[3-4]1,3−ジカルボキシ−5−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=COOH、n=2、Z2=アダマンタン環)
[3-5]1−カルボキシ−3−ヒドロキシ−5−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=OH,COOH、n=2、Z2=アダマンタン環)
[3-6]1−t−ブトキシカルボニル−3−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=t−ブトキシカルボニル基、n=1、Z2=アダマンタン環)
[3-7]1,3−ビス(t−ブトキシカルボニル)−5−(メタ)アクリロイルオキシアダマンタン[R=H又はCH3、R37=t−ブトキシカルボニル基、n=2、Z2=アダマンタン環]
[3-8]1−t−ブトキシカルボニル−3−ヒドロキシ−5−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=OH,t−ブトキシカルボニル基、n=2、Z2=アダマンタン環)
[3-9]1−(2−テトラヒドロピラニルオキシカルボニル)−3−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=2−テトラヒドロピラニルオキシカルボニル基、n=1、Z2=アダマンタン環)
[3-10]1,3−ビス(2−テトラヒドロピラニルオキシカルボニル)−5−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=2−テトラヒドロピラニルオキシカルボニル基、n=2、Z2=アダマンタン環)
[3-11]1−ヒドロキシ−3−(2−テトラヒドロピラニルオキシカルボニル)−5−(メタ)アクリロイルオキシアダマンタン(R=H又はCH3、R37=OH,2−テトラヒドロピラニルオキシカルボニル基、n=2、Z2=アダマンタン環)
アダマンタンエタノール43.2g、プロピオン酸ビニル48.1g、炭酸ナトリウム15.3g、トルエン120ml、ジ−μ−クロロビス(1,5−シクロオクタジエン)二イリジウム(I)1.62gの混合物を4つ口フラスコに入れ、窒素雰囲気下、100℃で加熱しつつ、4時間撹拌した。反応液中の沈殿を濾別し、濾液を減圧濃縮した。濃縮物を減圧蒸留精製し、下記式(8)で表される2−(アダマンタン−1−イル)エチルビニルエーテル34.8gを得た。
1H−NMR(CDCl3) δ:1.46(t, 2H), 1.53(d, 6H), 1.62-1.72(m, 6H), 1.95(m, 3H), 3.73(t, 2H), 3.96(m, 1H), 4.16(m, 1H), 6.46(m, 1H)
2−(アダマンタン−1−イル)エチルビニルエーテル32.8g、メタクリル酸68.4g、リン酸0.16g、4−メトキシフェノール0.164g、トルエン290mlの混合物を4つ口フラスコに入れ、窒素雰囲気下、20℃で6時間撹拌した。反応終了後、反応液を10重量%炭酸ナトリウム水溶液500mlで2回、10重量%食塩水500mlで1回洗浄し、有機層を減圧濃縮した。濃縮物をシリカゲルカラムクロマトグラフィーで精製し、下記式(9)で表される1−[2−(アダマンタン−1−イル)エトキシ]エチル(メタ)アクリレート38.6gを得た。
1H−NMR(CDCl3) δ:1.37-1.41(m, 2H), 1.43(d, 3H), 1.50(d, 6H), 1.60-1.71(m, 6H), 1.93(m, 3H), 1.96(m, 3H), 3.53(m, 1H), 3.72(m, 1H), 5.60(m, 1H), 5.97(m, 1H), 6.16(m, 1H)
下記式(10)で表されるボルニルビニルエーテル18.0g(0.1mol)、メタクリル酸43.0g(0.5mol)、リン酸98mg(1mmol)、4−メトキシフェノール12mg(0.1mmol)、トルエン180mlの混合物を4つ口フラスコに入れ、窒素雰囲気下、20℃で6時間撹拌した。反応終了後、反応液を10重量%炭酸ナトリウム水溶液200mlで2回、10重量%食塩水200mlで1回洗浄し、有機層を減圧濃縮した。濃縮物をシリカゲルカラムクロマトグラフィーで精製し、下記式(11)で表される1−(ボルニルオキシ)エチルメタクリレート22.8g(85mmol,収率85%)を得た。なお、ボルニルビニルエーテルは、(−)−ボルネオールとプロピオン酸ビニルから、特開2003−73321号公報に記載の方法を用いて合成し、蒸留精製したものを用いた。
1H−NMR(CDCl3) δ:0.80-0.84(m, 9H), 0.86(d, 1H), 1.18-1.27(m, 2H), 1.42-1.45(d, 3H), 1.57-1.70(m, 2H), 1.94(s, 3H), 1.95-1.99(m, 1H), 2.05-2.20(m, 1H), 3.79-3.82(m, 1H), 5.56(m, 1H), 5.97-6.00(m, 1H), 6.12(m, 1H)
下記構造の樹脂の合成
下記構造の樹脂の合成
下記構造の樹脂の合成
上記実施例及び比較例で得られた各ポリマーについて、該ポリマー100重量部とトリフェニルスルホニウムヘキサフルオロアンチモネート10重量部とを溶媒であるプロピレングリコールモノメチルエーテル(PGME)と混合して、ポリマー濃度17重量%のフォトレジスト用樹脂組成物を調製した。この組成物をシリオンウエハー上にスピンコーティング法により塗布し、厚み1.0μmの感光層を形成した。ホットプレートにより温度100℃で150秒間プリベークした後、波長247nmのKrFエキシマレーザーを用い、マスクを介して、照射量30mJ/cm2で露光した後、温度100℃で60秒間ポストベークした。次いで、0.3Mのテトラメチルアンモニウムヒドロキシド水溶液により60秒間現像し、純水でリンスした。その結果、実施例のポリマーを用いた場合は何れも、0.20μmのライン・アンド・スペースパターンが鮮明に精度よく得られたが、比較例のポリマーを用いた場合には、該パターンの精度は悪く鮮明さに欠けていた。
Claims (5)
- さらに、下記式(6a)〜(6g)、(7)
で表される単量体、無水マレイン酸、マレイミドから選択された少なくとも1種の単量体に対応する繰り返し単位を含む請求項2記載の高分子化合物。 - 請求項2又は3に記載の高分子化合物と光酸発生剤とを少なくとも含むフォトレジスト用樹脂組成物。
- 請求項4記載のフォトレジスト用樹脂組成物を基材又は基板上に塗布してレジスト塗膜を形成し、露光及び現像を経てパターンを形成する工程を含む半導体の製造方法。
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