KR20030005419A - 광활성 화합물 및 감광성 수지 조성물 - Google Patents
광활성 화합물 및 감광성 수지 조성물 Download PDFInfo
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- KR20030005419A KR20030005419A KR1020027016139A KR20027016139A KR20030005419A KR 20030005419 A KR20030005419 A KR 20030005419A KR 1020027016139 A KR1020027016139 A KR 1020027016139A KR 20027016139 A KR20027016139 A KR 20027016139A KR 20030005419 A KR20030005419 A KR 20030005419A
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- KR
- South Korea
- Prior art keywords
- group
- bis
- tert
- hydroxy
- groups
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 164
- 239000011342 resin composition Substances 0.000 title claims description 52
- 125000005647 linker group Chemical group 0.000 claims abstract description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 52
- 125000006239 protecting group Chemical group 0.000 claims abstract description 52
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 43
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 22
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 15
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 11
- -1 N-substituted carbamoyl group Chemical group 0.000 claims description 285
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 229920005989 resin Polymers 0.000 claims description 81
- 239000011347 resin Substances 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- 239000002585 base Substances 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000004450 alkenylene group Chemical group 0.000 claims description 23
- 125000002723 alicyclic group Chemical group 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 21
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000010703 silicon Substances 0.000 claims description 19
- 229910052710 silicon Inorganic materials 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 17
- 125000004419 alkynylene group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 15
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 15
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 15
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 229930185605 Bisphenol Natural products 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 125000001033 ether group Chemical group 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 9
- 125000000101 thioether group Chemical group 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001924 cycloalkanes Chemical class 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 217
- 238000003786 synthesis reaction Methods 0.000 description 217
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 189
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 130
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- 238000005160 1H NMR spectroscopy Methods 0.000 description 108
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 38
- 239000000243 solution Substances 0.000 description 36
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 26
- GDFUWFOCYZZGQU-UHFFFAOYSA-N 4-propoxybenzoic acid Chemical compound CCCOC1=CC=C(C(O)=O)C=C1 GDFUWFOCYZZGQU-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 23
- ISTOAGOBQCQLFG-UHFFFAOYSA-N [4-(4-bromophenyl)phenyl] tert-butyl carbonate Chemical group C1=CC(OC(=O)OC(C)(C)C)=CC=C1C1=CC=C(Br)C=C1 ISTOAGOBQCQLFG-UHFFFAOYSA-N 0.000 description 20
- 239000010410 layer Substances 0.000 description 20
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical group C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 20
- 150000002989 phenols Chemical class 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 20
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- UFPKPYIACUJDFD-UHFFFAOYSA-N tert-butyl (4-phenylmethoxyphenyl) carbonate Chemical compound C1=CC(OC(=O)OC(C)(C)C)=CC=C1OCC1=CC=CC=C1 UFPKPYIACUJDFD-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 230000035945 sensitivity Effects 0.000 description 14
- KXUKRZZEHBUWKN-UHFFFAOYSA-N tert-butyl (4-hydroxyphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(O)C=C1 KXUKRZZEHBUWKN-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 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 11
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- 238000011161 development Methods 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 10
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- XFUQJWQKYYIACT-UHFFFAOYSA-N (4-bromophenyl) tert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(Br)C=C1 XFUQJWQKYYIACT-UHFFFAOYSA-N 0.000 description 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 9
- NUPWGLKBGVNSJX-UHFFFAOYSA-N 1-bromo-4-propylbenzene Chemical compound CCCC1=CC=C(Br)C=C1 NUPWGLKBGVNSJX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003282 alkyl amino group Chemical group 0.000 description 9
- 125000005037 alkyl phenyl group Chemical group 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- HBMCQTHGYMTCOF-UHFFFAOYSA-N 4-hydroxyphenyl acetate Chemical compound CC(=O)OC1=CC=C(O)C=C1 HBMCQTHGYMTCOF-UHFFFAOYSA-N 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- UVFFOABHOIMLNB-UHFFFAOYSA-N 1-ethynyl-4-propylbenzene Chemical group CCCC1=CC=C(C#C)C=C1 UVFFOABHOIMLNB-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000010511 deprotection reaction Methods 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 235000013824 polyphenols Nutrition 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical class OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920000178 Acrylic resin Polymers 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 6
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012038 nucleophile Substances 0.000 description 6
- NMKZRVMAECEGMV-UHFFFAOYSA-N 1-ethynyl-4-propoxybenzene Chemical group CCCOC1=CC=C(C#C)C=C1 NMKZRVMAECEGMV-UHFFFAOYSA-N 0.000 description 5
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical class OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 5
- KVNNDSUUTJORDP-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxycarbonyloxy]benzoic acid Chemical compound CC(C)(C)OC(=O)OC1=CC=C(C(O)=O)C=C1 KVNNDSUUTJORDP-UHFFFAOYSA-N 0.000 description 5
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 5
- QBJGCSBAFMGNST-SKIQCWHVSA-N CCC[C@H](CC1)CC[C@@H]1C(C=C1)=CCC1(C(C)(C)C)C(O)=O Chemical compound CCC[C@H](CC1)CC[C@@H]1C(C=C1)=CCC1(C(C)(C)C)C(O)=O QBJGCSBAFMGNST-SKIQCWHVSA-N 0.000 description 5
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 125000004956 cyclohexylene group Chemical group 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
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- 230000007062 hydrolysis Effects 0.000 description 5
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 239000002244 precipitate Substances 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 5
- PDLJQUCQCVODPT-UHFFFAOYSA-N tert-butyl 3-[4-[9-[4-[3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]fluoren-9-yl]phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OC(C)(C)C)=CC=C1C1(C=2C=CC(C=CC(=O)OC(C)(C)C)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 PDLJQUCQCVODPT-UHFFFAOYSA-N 0.000 description 5
- DAHBOTUNPDMTAI-UHFFFAOYSA-N tert-butyl [4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl] carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(OC(=O)OC(C)(C)C)C=C1 DAHBOTUNPDMTAI-UHFFFAOYSA-N 0.000 description 5
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 5
- BUJZENMUXBWWFE-UHFFFAOYSA-N (4-propoxyphenyl)methanol Chemical compound CCCOC1=CC=C(CO)C=C1 BUJZENMUXBWWFE-UHFFFAOYSA-N 0.000 description 4
- DYRRGZZBNFNVLA-UHFFFAOYSA-N (6-bromonaphthalen-2-yl) tert-butyl carbonate Chemical compound C1=C(Br)C=CC2=CC(OC(=O)OC(C)(C)C)=CC=C21 DYRRGZZBNFNVLA-UHFFFAOYSA-N 0.000 description 4
- ATBOOPHPGQNHSL-UHFFFAOYSA-N 1-(1-ethoxyethoxy)-4-propan-2-ylbenzene Chemical compound CCOC(C)OC1=CC=C(C(C)C)C=C1 ATBOOPHPGQNHSL-UHFFFAOYSA-N 0.000 description 4
- OCGNQJCQAQWYOI-UHFFFAOYSA-N 1-(chloromethyl)-4-propylbenzene Chemical compound CCCC1=CC=C(CCl)C=C1 OCGNQJCQAQWYOI-UHFFFAOYSA-N 0.000 description 4
- DVDHNHPHNIXHCU-UHFFFAOYSA-N 1-bromo-4-[[(4-bromophenyl)-phenylmethoxy]-phenylmethyl]benzene Chemical compound C1=CC(Br)=CC=C1C(C=1C=CC=CC=1)OC(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 DVDHNHPHNIXHCU-UHFFFAOYSA-N 0.000 description 4
- LHBXACFBTZEWCK-UHFFFAOYSA-N 1-propoxycyclohexa-2,4-dien-1-ol Chemical compound CCCOC1(O)CC=CC=C1 LHBXACFBTZEWCK-UHFFFAOYSA-N 0.000 description 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 4
- HTSCPVPNXMPNQZ-UHFFFAOYSA-N 4-(4-pentylphenyl)phenol Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(O)C=C1 HTSCPVPNXMPNQZ-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
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- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
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- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C—CHEMISTRY; METALLURGY
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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- C07C2603/02—Ortho- or ortho- and peri-condensed systems
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- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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Abstract
Description
Claims (22)
- 감광제와 조합하여 사용되며, 하기 화학식 1로 표시되는 광활성 화합물.<화학식 1>A-[(J)m-(X-Pro)]n식 중, A는 탄화수소기 및 복소환기로부터 선택된 1종 이상의 소수성기로 구성된 소수성 단위를 나타내며, J는 연결기를 나타내고, X-Pro는 광조사에 의해 이탈 가능한 보호기 Pro로 보호된 친수성기를 나타낸다. m은 0 내지 1, n은 1 이상의 정수이다.
- 제1항에 있어서, 보호기 Pro가 광조사에 의해, 감광제와 관련하여 이탈 가능한 광활성 화합물.
- 제1항에 있어서, 보호기 Pro가 소수성 보호기이고, 이 소수성 보호기의 이탈에 의해, 히드록실기 또는 카르복실기가 생성 가능한 광활성 화합물.
- 제1항에 있어서, 보호기 Pro가 (i) 알콕시알킬기, 아실기, 알콕시카르보닐기, 옥사시클로알킬기, 가교환식 지환족기, 및 알킬실릴기로부터 선택된 히드록실기에 대한 보호기, 또는 (ii) 알킬기, 가교환식 지환족 탄화수소기, 옥사시클로알킬기, 락톤환기, 및 카르바모일기 또는 N-치환 카르바모일기로부터 선택된 카르복실기에 대한 보호기인 광활성 화합물.
- 제1항에 있어서, 화학식 1에서 소수성 단위 A가 지방족 탄화수소기, 지환족 탄화수소기 또는 방향족 탄화수소기로 구성되고, 친수성기가 히드록실기 또는 카르복실기이고, 보호기 Pro가 (i) C1-6알킬-카르보닐기, C1-6알콕시-C1-6알킬기, C1-6알콕시-카르보닐기, 옥사시클로알킬기, 비- 또는 트리시클로알킬기, 및 C1-6알킬실릴기로부터 선택된 히드록실기에 대한 보호기, 또는 (ii) C1-6알킬기, 비- 또는 트리시클로알킬기, 카르바모일기, N-C1-6알킬-카르바모일기 및 N-C6-10아릴-카르바모일기로부터 선택된 카르복실기에 대한 보호기인 광활성 화합물.
- 제1항에 있어서, 연결기 J가 알킬렌기, 알케닐렌기, 알키닐렌기, 시클로알킬렌기, 아릴렌기, 옥시알킬렌기, 알킬렌옥시기, 폴리(옥시알킬렌)기, 에테르기, 티오에테르기, 카르보닐기, 카르보닐옥시기, 옥시카르보닐기, 아미드기, 우레탄기, 또는 요소기인 광활성 화합물.
- 제1항에 있어서, 화학식 1에 있어서, n이 1 내지 10의 정수인 광활성 화합물.
- 제1항에 있어서, 하기 화학식 3b로 표시되는 광활성 화합물.<화학식 3b>식 중, Z1은 동일하거나 상이하고, 탄화수소환 또는 복소환을 나타내며, R1은 동일하거나 상이하고, 할로겐 원자, 알킬기, 알콕시기, 알콕시카르보닐기, 시클로알킬기, 아릴기, 아랄킬기, 또는 규소 함유기를 나타내며, r은 0 내지 1 이상의 정수를 나타낸다. J, m, X, Pro, n은 상기와 동일하다.
- 제9항에 있어서, Z1은 C4-40지환족 탄화수소 또는 C6-40방향족 탄화수소이고, R1은 동일하거나 상이하고, 할로겐 원자, 알킬기, 알콕시기, 시클로알킬기 또는 규소 함유기이고, r은 0 내지 4이고, J는 알킬렌기, 알케닐렌기 또는 알키닐렌기이고, m은 0 또는 1이며, n은 1 내지 6인 광활성 화합물.
- 제1항에 있어서, 하기 화학식 4b로 표시되는 광활성 화합물.<화학식 4b>식 중, Z2및 Z3은 동일하거나 상이하고, 탄화수소환 또는 복소환을 나타내며, A3은 알킬렌기, 알케닐렌기, 알키닐렌기, 시클로알킬렌기, 아릴렌기, 옥시알킬렌기, 알킬렌옥시기, 에테르기, 티오에테르기, 카르보닐기, 카르보닐옥시기, 옥시카르보닐기, 아미드기, 우레탄기, 요소기, 술포닐기로부터 선택된 연결기를 나타내며, s 및 u는 동일하거나 상이하고, 0 또는 1이다. J1a및 J1b는 동일하거나 상이하고, A3과 상이한 연결기를 나타내며, R1a및 R1b는 동일하거나 상이하고, 할로겐 원자, 알킬기, 알콕시기, 알콕시카르보닐기, 시클로알킬기, 아릴기, 아랄킬기, 또는 규소 함유기를 나타내고, n1 및 n2는 각각 독립적으로 0 또는 1 이상의 정수이고, n1+n2≥1이다. r, m, X, Pro는 상기와 동일하다.
- 제10항에 있어서, 연결기 A3이 직접 결합, 알킬렌기, 알케닐렌기, 알키닐렌기, 옥시알킬렌기, 알킬렌옥시기, 에테르기, 티오에테르기, 카르보닐기, 카르보닐옥시기, 옥시카르보닐기, 아미드기, 우레탄기, 요소기 또는 술포닐기일 때, u는 0이고, 연결기 A3이 시클로알킬렌기 또는 아릴렌기일 때, u는 1인 광활성 화합물.
- 제10항에 있어서, 연결기 A3이 시클로알킬렌기 또는 아릴렌기일 때, 연결기 J1a및 J1b가, 직접 결합 또는 알킬렌기인 광활성 화합물.
- 제10항에 있어서, 연결기 A3이 시클로알킬렌기 또는 아릴렌기일 때 연결기 J1a및 J1b가 할로겐 원자, 알킬기, 시클로알킬기, 아릴기로부터 선택된 치환기를 포함할 수도 있는 알킬렌기인 광활성 화합물.
- 제10항에 있어서, Z2-(J1a)u-(A3)s-(J1b)u-Z3로 표시되는 소수성 단위는 (a) 비페놀류, (b) 비스(히드록시아릴) C1-10알칸류, (c) 비스(히드록시아릴)시클로알칸류, (d) A3이 카르보닐기, 산소 원자, 에스테르기, 알킬렌옥시기, 옥시알킬렌기, 아미드기 또는 술포닐기인 비스페놀류, (e) A3가 벤젠환이고, J1a및 J1b가 알킬렌기인 비스페놀류 및 (h) 플루오렌 골격을 갖는 비스페놀류로부터 선택된 화합물에 대응하는 소수성 단위이고, n1+n2=1 내지 10인 광활성 화합물.
- 기재 수지와 감광제와 제1항에 기재된 광활성 화합물로 구성되어 있는 감광성 수지 조성물.
- 제15항에 있어서, 물 또는 알칼리 현상이 가능한 감광성 수지 조성물.
- 제15항에 있어서, 포지티브형 감광성 수지 조성물인 감광성 수지 조성물.
- 제15항에 있어서, 기재 수지가 산의 작용에 의해 친수성기를 생성 가능한 수지로 구성되고, 감광제가 광산 발생제로 구성되어 있는 감광성 수지 조성물.
- 제15항에 있어서, 기재 수지가 히드록실기 및 카르복실기로부터 선택되고, 또한 산의 작용에 의해 이탈 가능한 보호기로 보호 가능한 친수성기를 갖는 단량체의 단독 또는 공중합체로 구성되어 있는 감광성 수지 조성물.
- 제15항에 있어서, 광활성 화합물과 감광제의 비율(중량비)가 광활성 화합물/감광제=0.01/1 내지 100/1인 감광성 수지 조성물.
- 제15항에 있어서, 감광제의 사용량이 기재 수지 100 중량부에 대하여 0.1 내지 50 중량부이고, 광활성 화합물의 사용량이 기재 수지 100 중량부에 대하여 1 내지 1000 중량부인 감광성 수지 조성물.
- 제15항에 기재된 감광성 수지 조성물을 기판에 도포하여, 노광한 후, 가열 처리하고 현상하여 패턴을 형성하는 방법.
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-
2002
- 2002-03-29 KR KR1020027016139A patent/KR100876047B1/ko active IP Right Grant
- 2002-03-29 EP EP02713248A patent/EP1375463A4/en not_active Withdrawn
- 2002-03-29 WO PCT/JP2002/003140 patent/WO2002079131A1/ja active Application Filing
- 2002-03-29 US US10/296,831 patent/US7534547B2/en active Active
Cited By (5)
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WO2008004751A1 (en) * | 2006-07-05 | 2008-01-10 | Industry-Academic Cooperation Foundation, Yonsei University | Aromatic polymers having optical activity and preparation methods thereof |
KR100794527B1 (ko) * | 2006-07-05 | 2008-01-17 | 연세대학교 산학협력단 | 광활성 방향족 중합체 및 이의 제조방법 |
US9902675B2 (en) | 2013-03-29 | 2018-02-27 | Tokyo Ohka Kogyo Co., Ltd. | Vinyl-group-containing fluorene compound |
US9914687B2 (en) | 2013-03-29 | 2018-03-13 | Tokyo Ohka Kogyo Co., Ltd. | Composition containing vinyl-group-containing compound |
US10233269B2 (en) | 2013-03-29 | 2019-03-19 | Tokyo Ohka Kogyo Co., Ltd. | Compound containing structural unit derived from vinyl ether compound |
Also Published As
Publication number | Publication date |
---|---|
US7534547B2 (en) | 2009-05-19 |
WO2002079131A1 (fr) | 2002-10-10 |
EP1375463A4 (en) | 2009-09-02 |
US20030211421A1 (en) | 2003-11-13 |
KR100876047B1 (ko) | 2008-12-26 |
EP1375463A1 (en) | 2004-01-02 |
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