JP4484479B2 - フルオレン誘導体及び光活性化合物 - Google Patents
フルオレン誘導体及び光活性化合物 Download PDFInfo
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- JP4484479B2 JP4484479B2 JP2003328520A JP2003328520A JP4484479B2 JP 4484479 B2 JP4484479 B2 JP 4484479B2 JP 2003328520 A JP2003328520 A JP 2003328520A JP 2003328520 A JP2003328520 A JP 2003328520A JP 4484479 B2 JP4484479 B2 JP 4484479B2
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- Prior art keywords
- group
- fluorene
- bis
- alkyl
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 title description 57
- -1 2-methyl-2-norbornyl group Chemical group 0.000 claims description 192
- 229920005989 resin Polymers 0.000 claims description 73
- 239000011347 resin Substances 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 239000011342 resin composition Substances 0.000 claims description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
- 239000002585 base Substances 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 24
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 238000011161 development Methods 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 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 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 155
- 150000002220 fluorenes Chemical class 0.000 description 113
- 239000002904 solvent Substances 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 46
- 125000006239 protecting group Chemical group 0.000 description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 43
- 125000001424 substituent group Chemical group 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 125000003545 alkoxy group Chemical group 0.000 description 32
- 238000000034 method Methods 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 239000000178 monomer Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 239000003377 acid catalyst Substances 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 230000035945 sensitivity Effects 0.000 description 14
- 150000003573 thiols Chemical class 0.000 description 14
- 239000003504 photosensitizing agent Substances 0.000 description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
- 150000002989 phenols Chemical group 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
- 125000002723 alicyclic group Chemical group 0.000 description 10
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 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 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 8
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 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 7
- 238000010511 deprotection reaction Methods 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 150000008376 fluorenones Chemical class 0.000 description 7
- 150000008282 halocarbons Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PTBCCLLVPOLXES-UHFFFAOYSA-N 2-[9-(2-hydroxyphenyl)fluoren-9-yl]phenol Chemical class OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)C2=CC=CC=C2C2=CC=CC=C21 PTBCCLLVPOLXES-UHFFFAOYSA-N 0.000 description 6
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 150000004292 cyclic ethers Chemical class 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 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 6
- 239000002841 Lewis acid Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 5
- 150000005215 alkyl ethers Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000012953 triphenylsulfonium Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- RAIOQXXWEGZKAI-UHFFFAOYSA-N 4-[9-(3,4-dihydroxyphenyl)fluoren-9-yl]benzene-1,2-diol Chemical compound C1=C(O)C(O)=CC=C1C1(C=2C=C(O)C(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RAIOQXXWEGZKAI-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000003759 ester based solvent Substances 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000005453 ketone based solvent Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003871 sulfonates Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 3
- PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 3
- GGANEIOSDSVALY-UHFFFAOYSA-N 4-[9-(2,3,4-trihydroxyphenyl)fluoren-9-yl]benzene-1,2,3-triol Chemical class OC1=C(C=CC(=C1O)O)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=C(C(=C(C=C1)O)O)O GGANEIOSDSVALY-UHFFFAOYSA-N 0.000 description 3
- MAGUHAAQVHMRFN-UHFFFAOYSA-N 9,9-bis[4-(2-ethoxyethoxy)phenyl]fluorene Chemical compound C1=CC(OCCOCC)=CC=C1C1(C=2C=CC(OCCOCC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 MAGUHAAQVHMRFN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JCSIWUUYTDLVSQ-UHFFFAOYSA-N CCOCCOC1=C(C=C(C=C1)C2(C3=CC=CC=C3C4=CC=CC=C42)C5=CC(=C(C=C5)OCCOCC)C)C Chemical compound CCOCCOC1=C(C=C(C=C1)C2(C3=CC=CC=C3C4=CC=CC=C42)C5=CC(=C(C=C5)OCCOCC)C)C JCSIWUUYTDLVSQ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 150000002596 lactones Chemical group 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Description
I. Sondi and E. Matijevic, Resist Technology and Processing XVII, Francis M. Houlihan, Editor, Proceedings of SPIE Vol. 3999(2000)(第627〜637頁)
前記式(I)において、−X1−Pro1及び−X2−Pro2は保護基で保護されたヒドロキシル基又はカルボキシル基であってもよい。また、Pro1及びPro2はアセタール系保護基又はアルキルエステル系保護基であってもよく、例えば、−(J1)m1−X1−Pro1及び−(J2)m2−X2−Pro2が、−O−CH(Ra)−ORb又は−O−C(O)−ORc(式中、Ra〜Rcは、同一又は異なって、アルキル基を示す)であってもよい。さらに、−(J1)m1−X1−Pro1及び−(J2)m2−X2−Pro2は、−C(Rd)=C(Re)−C(O)−ORf(式中、Rd及びReは水素原子又はアルキル基を示し、Rfはアルキル基を示す)であってもよい。式(I)において、通常、p1及びp2は0〜2の整数、q1及びq2は0であり、R1及びR2がアルキル基である。
フルオレン誘導体(I)において、連結基J1及びJ2は、例えば、直接結合、アルキレン基[メチレン、エチレン、ジメチルメチレン、ジ(トリフルオロメチル)メチレン、プロピレン、トリメチレン、テトラメチレン、t−ブチレンなどの直鎖又は分岐鎖状アルキレン基(C1-6アルキレン基など)]、アルケニレン基[ビニレン、イソプロペニレン、プロペニレンなどのC2-4アルケニレン基など]、アルキニレン基[エチニレン基などのC2-4アルキニレン基など]、シクロアルキレン基[シクロヘキシレン基などのC4-8シクロアルキレン基など]、アリーレン基[フェニレン基などのC6-10アリーレン基など]であってもよい。なお、連結基の繰り返し数m1及びm2は0又は1である。
フルオレン類(b)および(c)は、酸触媒の存在下、下記式(1)で表されるフルオレノン類と、下記式(2)で表される多価フェノール類とを反応させることにより得ることができる。
なお、前記式(2)において、Rは、前記R1又はR2に対応しており、nは前記n1又はn2に対応しており、pは前記p1又はp2に対応しており、好ましい態様などは前記例示のとおりである。前記式(1)で表される代表的なフルオレノン類は、9−フルオレノン(q1=q2=0)である。
前記フルオレン誘導体(I)は、光活性化合物(感光性化合物)として有用であり、感光剤と組み合わせて用いられる。特にレジスト用途において、フルオレン誘導体(I)を用いると、レジストのベース樹脂との親和性や現像剤に対する溶解性を制御しやすい。そのため、保護基Proは、光照射により、感光剤と関連して脱離可能である。
本発明では、光活性化合物である前記フルオレン誘導体(I)と、前記感光剤と、ベース樹脂(オリゴマー又はポリマー)とで感光性樹脂組成物(又はレジスト組成物)を構成できる。感光性樹脂組成物は、有機溶媒(アルコール類など)により現像可能であってもよいが、通常、水又はアルカリ現像可能であるのが好ましい。
ベース樹脂としては、例えば、ヒドロキシル基含有ポリマー[ポリビニルアセタール、ポリビニルアルコール、エチレン−ビニルアルコール共重合体、ヒドロキシル基含有セルロース誘導体(ヒドロキシエチルセルロースなど)、ポリビニルフェノール系樹脂、ノボラック樹脂(フェノールノボラック樹脂)など]、カルボキシル基含有ポリマー[重合性不飽和カルボン酸((メタ)アクリル酸、無水マレイン酸、イタコン酸など)を含む単独又は共重合体、カルボキシル基含有セルロース誘導体(カルボキシメチルセルロース又はその塩など)など]、エステル基含有ポリマー[カルボン酸ビニルエステル(酢酸ビニルなど)、(メタ)アクリル酸エステル(メタクリル酸メチルなど)などの単量体の単独または共重合体(ポリ酢酸ビニル、エチレン−酢酸ビニル共重合体、(メタ)アクリル系樹脂など)、ポリエステル、セルロースエステル類など]、エーテル基を有するポリマー[ポリアルキレンオキシド、ポリオキシアルキレングリコール、ポリビニルエーテル系樹脂、ケイ素樹脂、セルロースエーテル類など]、カーボネート基含有ポリマー、アミド基又は置換アミド基を有するポリマー[ポリビニルピロリドン、ポリウレタン系重合体、ポリ尿素、ナイロン又はポリアミド系重合体(ラクタム成分、ジカルボン酸成分やジアミン成分を用いたポリアミドなど);ポリ(メタ)アクリルアミド系重合体;ポリアミノ酸;ビュレット結合を有するポリマー;アロハネート結合を有するポリマー;ゼラチンなどの蛋白類など]、ニトリル基を有するポリマー(アクリロニトリル系重合体など)、グリシジル基を有するポリマー(エポキシ樹脂、グリシジル(メタ)アクリレートの単独又は共重合体など)、ハロゲン含有ポリマー(ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、塩化ビニリデン系ポリマー、塩素化ポリプロピレンなど)、非芳香族性環基を有するポリマー(例えば、(メタ)アクリル酸シクロヘキシルなどのC5-8シクロアルキル基を有するポリマー;(メタ)アクリル酸ノルボルニル、(メタ)アクリル酸アダマンチルなどの架橋環式C7-20炭化水素環基を有するポリマーなど)、重合性オリゴマー又はポリマー((メタ)アクリロイル基、アリル基、ビニル基、シンナモイル基などの重合性基を有するオリゴマー又はポリマーなど)などが例示できる。これらのベース樹脂は単独で又は2種以上組合わせて使用してもよい。ベース樹脂としては、ネガ型感光性樹脂組成物を構成するベース樹脂でもよいが、ポジ型感光性樹脂組成物(ポジ型レジスト)を構成するためのベース樹脂が好ましい。
前記フルオレン誘導体(I)と感光剤との割合(重量比)は、前者/後者=0.01/1〜100/1程度の広い範囲から選択でき、通常、0.1/1〜75/1、好ましくは1/1〜50/1程度であってもよい。
前記感光性樹脂組成物を基体(基板)に適用(塗布又は被覆)することにより感光層を形成できる。基体(基板)としては、パターンの特性や用途に応じて、金属(アルミニウム),ガラス,セラミックス(アルミナ,銅ドープアルミナ,タングステンシリケートなど),プラスチックなどから適当に選択でき、シリコンウェハーなどの半導体基板であってもよい。
パターン(特に微細なパターン)は、露光,現像やエッチングなどを組み合わせた慣用のリソグラフィー技術を利用して行うことができる。
テトラヒドロフラン50ml中に、9,9−ビス(4−ヒドロキシフェニル)フルオレン27.7g(0.079モル)、エチルビニルエーテル40g(0.56モル)、塩酸−エーテル溶液(1モル/リットル)5mlを加えて40℃に加熱し、約5時間攪拌した。反応終了後、炭酸水素ナトリウム水溶液で洗浄後、水洗し溶媒を留去した。シリカゲルカラムクロマトグラフィー(溶出液:ヘキサン)にて精製することにより9,9−ビス{4−[(1−エトキシ)エトキシ]フェニル}フルオレン35.7g(収率86%)を得た。
9,9−ビス(4−ヒドロキシフェニル)フルオレンの代わりに9,9−ビス(3−メチル−4−ヒドロキシフェニル)フルオレン30g(0.079モル)を用いる以外は実施例1と同様にして9,9−ビス{3−メチル−4−[(1−エトキシ)エトキシ]フェニル}フルオレン39.8g(収率91%)を得た。
脱水酢酸エチル50ml中に、9,9−ビス(4−ヒドロキシフェニル)フルオレン12.9g(36.7ミリモル)、塩酸/エーテル溶液(1モル/リットル)1.7mlを加えて40℃に設定した。この中にエチルビニルエーテル7.9g(109.6ミリモル)を滴下し一晩攪拌した。反応終了後、炭酸水素ナトリウム水溶液で洗浄後、水洗し溶媒を除去した。シリカゲルカラムクロマトグラフィー(溶出液:トルエン)にて精製することにより9,9−ビス{4−[(1−エトキシ)エトキシ]フェニル}フルオレン14.1g(収率78%)を得た。
脱水アセトン50mlに、9,9−ビス(4−ヒドロキシフェニル)フルオレン12.9g(36.7ミリモル)と4−ジメチルアミノピリジン[(CH3)2NC5H4N]4.5mg(3.7×10-2ミリモル)とを加え、40℃に加熱した後、ジ−tert−ブチルジカーボネート8g(36.7ミリモル)を滴下し24時間攪拌した。反応終了後、反応液を氷水に入れ最少量の水酸化カリウムでアルカリ性に調整し、生成した固体を濾過、乾燥し、トルエンで再結晶することにより9,9−ビス[4−(tert−ブトキシカルボニルオキシ)フェニル]フルオレン18.2g(収率90%)を得た。
脱水アセトン50mlに、9,9−ビス(4−ヒドロキシフェニル)フルオレン12.9g(36.7ミリモル)と4−ジメチルアミノピリジン[(CH3)2NC5H4N]4.5mg(3.7×10-2ミリモル)とを加え、40℃に加熱した後、ジ−tert−ブチルジカーボネート4g(18.4ミリモル)を滴下し24時間攪拌した。反応終了後、反応液を氷水に入れ最少量の水酸化カリウムでアルカリ性に調整し、生成した固体を濾過、乾燥した後、シリカゲルカラム(溶出液:ヘキサン/酢酸エチル=7/3)で精製することにより9−[4−(tert−ブトキシカルボニルオキシ)フェニル]9−[4−ヒドロキシフェニル]フルオレン12.1g(収率73%)を得た。
(i)9,9−ビス[4−(トリフルオロメチルスルホニルオキシ)フェニル]フルオレンの合成
9,9−ビス(4−ヒドロキシフェニル)フルオレン5.2g(14.9ミリモル)を脱水ピリジン(C5H5N)50mlに溶解し、さらに無水トリフルオロメタンスルホン酸8.8g(31.2ミリモル)を氷冷下で加えて室温で24時間反応させた。反応溶液を氷水の中へ投入後、塩酸を加えて系内を酸性にした。生じた固体をろ過、水洗、乾燥後、ヘキサン/酢酸エチル混合溶媒で再結晶することにより9,9−ビス[4−(トリフルオロメチルスルホニルオキシ)フェニル]フルオレン6.51g(10.6ミリモル)を得た。
ステップ(i)で合成した9,9−ビス[4−(トリフルオロメチルスルホニルオキシ)フェニル]フルオレン7.4g(21.2ミリモル)に,アクリル酸tert−ブチル2.85g(22.2ミリモル),トリエチルアミン10ml,アセトニトリル30ml,酢酸パラジウム[Pd(OAc)2]50mg(2.22×10-1ミリモル),トリ−o−トリルホスフィン134mg(4.42×10-1ミリモル)を加え反応系中をアルゴンで置換した後、加熱還流下24時間反応させた。反応溶液を氷水500mlの中へ投入後攪拌しながら塩酸を添加し、攪拌し得られた固体を濾過、水洗、乾燥後、シリカゲルカラムクロマトグラフィー(溶出液:トルエン)にて精製することにより、9,9−ビス[4−(2−tert−ブトキシカルボニルビニル)フェニル]フルオレン8.34g(収率69%)を得た。
9−フルオレノン36g(約0.2モル)、カテコール88g(約0.8モル)、β-メルカプトプロピオン酸0.7ml、および1,4−ジオキサン60gを反応器に入れ、80℃の加熱状態で98%硫酸5mlを滴下した。反応終了後、MIBK(メチルイソブチルケトン)200mlおよび水100mlを加えて抽出した。同操作を3回行うことによって、余剰の硫酸を除去した。溶媒濃縮後、MIBK100mlおよびトルエン200mlを加えたのち、10℃まで冷却することによってビスカテコールフルオレン[9,9−ビス(3,4−ジヒドロキシフェニル)フルオレン]65gを得た。以下に、得られたビスカテコールフルオレンの1H−NMRスペクトルデータを示す。
ヒドロキシル基のうち35モル%を1−エトキシエトキシ基で保護した重量平均分子量9,000のポリビニルフェノール樹脂0.5重量部に、ヒドロキシル基のうち37モル%をt−BOC(tert−ブトキシカルボニルオキシ)基で置換した重量平均分子量8,500のポリビニルフェノール樹脂0.5重量部を加え、下記式(A)で表される光酸発生剤0.02重量部を添加し、溶媒としてのプロピレングリコールモノメチルエーテルアセテート6重量部を混合することによりポジ型フォトレジストを調製した。
前記ステップ(1)で得られた感光性樹脂溶液に、実施例1又は3で得られたフルオレン誘導体を添加し、フッ素樹脂(ポリテトラフルオロエチレン)(0.2μm)製フィルターで濾過して感光性樹脂組成物を得た。なお、表1に示す割合は、前記感光性樹脂溶液の溶剤を除く固形分に対する割合である。
洗浄したシリコンウエハーをヘキサメチルジシラザンで処理した後、前記ステップ(2)で得られた感光性樹脂組成物を、スピンコーターを用いて乾燥後の膜厚が0.4μmとなるように塗布し、ホットプレートにて100℃で1分間加熱した。次いで、248nm(KrFエキシマーレーザー)の露光波長を有する縮小投影露光機(キャノン(株)製、FPA−3000EX5,NA=0.63)を用いて、線幅の異なるラインアンドスペースパターンを有するテストマスクを介して、露光量を段階的に変えて露光した。このウエハーをホットプレートにて100℃で1分間加熱した後、2.38重量%のテトラメチルアンモニウムハイドロオキサイド水溶液で1分間パドル現像してポジ型パターンを得た。
(i)感度:ライン幅0.25μmのライン:スペース=1:1がマスク寸法どおりになる露光量で表示した(値が小さいほど高感度で良好)。
(ii)解像度:ライン幅0.25μmのライン:スペース=1:1がマスク寸法どおりになる露光量でラインが分離する最小寸法で表示した(値が小さいほど高解像度で良好)。
Claims (4)
- 酸の作用により親水性基を生成可能な樹脂で構成されたベース樹脂と、光酸発生剤で構成された感光剤と、下記式(I)で表されるフルオレン誘導体とで構成され、水又はアルカリ現像可能である感光性樹脂組成物。
−X1−Pro1及び−X2−Pro2はそれぞれ脱離可能な保護基Pro1又はPro2で保護された親水性基であって、X1およびX2は、ヒドロキシル基、−O−(AO)r−H基(式中、AはC2−4アルキレン基、rは1以上の整数を示す)、又はカルボキシル基であり、
X1及びX2がヒドロキシル基又は−O−(AO)r−H基のとき、保護基Pro1又はPro2は、C1−6アルキル−カルボニル基、C1−6アルコキシカルボニル基、5又は6員オキサシクロアルキル基、2−ノルボルニル基、2−メチル−2−ノルボルニル基、2−アダマンチル基、2−メチル−2−アダマンチル基、C1−6アルコキシ−C1−6アルキル基、又は直鎖状又は分岐鎖状トリC1−4アルキルシリル基であり、
X1及びX2がカルボキシル基のとき、保護基Pro1又はPro2は、C1−4アルキル基、2−ノルボルニル基、2−メチル−2−ノルボルニル基、2−アダマンチル基、2−メチル−2−アダマンチル基、テトラヒドロフラン−3−イル基、3−メチルテトラヒドロフラン−3−イル基、テトラヒドロピラン−3−イル基、3−メチルテトラヒドロピラン−3−イル基、テトラヒドロ−2−フラノン−4−イル基、4−メチルテトラヒドロ−2−フラノン−4−イル基、テトラヒドロ−2−ピロン−4−イル基、4−メチルテトラヒドロ−2−ピロン−4−イル基、カルバモイル基、N−C1−6アルキル−カルバモイル基、又はC6−10アリールカルバモイル基であり、
R1〜R4はC1−6アルキル基、C2−6アルケニル基、C1−6アルコキシ基、C4−8シクロアルキル基、フェニル基、C1−4アルキルフェニル基、ナフチル基、又はハロゲン原子を表し、
m1及びm2は0又は1、n1及びn2は2〜4の整数、p1、p2、q1及びq2は0〜4の整数を表す。但し、n1+p1及びn2+p2は、5以下の整数である。) - 式(I)において、p1及びp2が0〜2の整数、q1及びq2が0であり、R1及びR2がC1−6アルキル基である請求項1記載の感光性樹脂組成物。
- ポジ型感光性樹脂組成物である請求項1記載の感光性樹脂組成物。
- 請求項1記載のフルオレン誘導体で構成されたレジスト用添加剤。
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JP4614056B2 (ja) * | 2003-09-18 | 2011-01-19 | 三菱瓦斯化学株式会社 | レジスト用化合物および感放射線性組成物 |
EP1666970A4 (en) * | 2003-09-18 | 2009-09-02 | Mitsubishi Gas Chemical Co | COMPOSITION FOR RESIST AND RADIATION COMPATIBLE COMPOSITION |
JP4685418B2 (ja) * | 2004-11-25 | 2011-05-18 | 大阪瓦斯株式会社 | フルオレン誘導体および感光性樹脂組成物 |
TWI494697B (zh) | 2004-12-24 | 2015-08-01 | Mitsubishi Gas Chemical Co | 光阻用化合物 |
TW200745010A (en) * | 2006-02-17 | 2007-12-16 | Jsr Corp | Compound having acid dissociable group and radiation sensitive composition containing the same |
JP4780586B2 (ja) * | 2006-05-08 | 2011-09-28 | 旭化成イーマテリアルズ株式会社 | ポジ型感光性樹脂組成物 |
JP5543817B2 (ja) * | 2010-03-24 | 2014-07-09 | 大阪ガスケミカル株式会社 | フルオレン誘導体およびその製造方法 |
JP5846622B2 (ja) * | 2010-12-16 | 2016-01-20 | 富士フイルム株式会社 | 感光性樹脂組成物、硬化膜、硬化膜の形成方法、有機el表示装置、及び、液晶表示装置 |
JP5210372B2 (ja) * | 2010-12-22 | 2013-06-12 | 大阪瓦斯株式会社 | 感光性樹脂組成物およびパターン形成方法 |
JP6357148B2 (ja) * | 2013-03-29 | 2018-07-11 | 東京応化工業株式会社 | ビニル基含有化合物を含有する組成物 |
WO2014157674A1 (ja) * | 2013-03-29 | 2014-10-02 | 東京応化工業株式会社 | ビニルエーテル化合物に由来する構造単位を含む化合物 |
JP6342887B2 (ja) * | 2013-03-29 | 2018-06-13 | 東京応化工業株式会社 | ビニル基含有フルオレン系化合物 |
CN105190437A (zh) * | 2013-06-14 | 2015-12-23 | 富士胶片株式会社 | 感光性树脂组合物、硬化物及其制造方法、树脂图案制造方法、硬化膜、液晶显示装置、有机el显示装置以及触摸屏显示装置 |
KR101949589B1 (ko) * | 2017-05-12 | 2019-02-18 | 차혁진 | 화학증폭형 바인더 수지 및 이를 포함하는 포지티브 감광성 고굴절 유기절연막 조성물 |
WO2021033738A1 (ja) * | 2019-08-22 | 2021-02-25 | 富士フイルム株式会社 | 硬化性組成物、硬化物、光学部材、およびレンズ |
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US5061809A (en) * | 1990-05-25 | 1991-10-29 | Air Products And Chemicals, Inc. | 9,9-bis-(3,4-dicarboxyphenyl)fluorene dianhydrides |
ATE137231T1 (de) * | 1990-09-13 | 1996-05-15 | Ocg Microelectronic Materials | Säurelabile lösungsinhibitoren und darauf basierende positiv und negativ arbeitende strahlungsempfindliche zusammensetzung |
JPH05170702A (ja) * | 1991-08-06 | 1993-07-09 | Daiso Co Ltd | 新規なビスフェノール誘導体とその製造法 |
JP2801494B2 (ja) * | 1993-04-01 | 1998-09-21 | 帝人株式会社 | ジアリル化合物および該化合物を用いた架橋重合体の製造方法 |
US5447960A (en) * | 1993-10-04 | 1995-09-05 | Dowelanco | Fungicidal use of phenolic aromatic compounds |
JPH08101501A (ja) * | 1994-10-03 | 1996-04-16 | Nippon Paint Co Ltd | 体積ホログラム記録用感光性組成物、及びそれを用いた記録媒体ならびに体積ホログラム形成方法 |
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JP2002047335A (ja) * | 2000-08-03 | 2002-02-12 | Osaka Gas Co Ltd | フルオレン系光重合性樹脂組成物、その硬化物および製造方法 |
JP2002088136A (ja) * | 2000-09-12 | 2002-03-27 | Nagase Kasei Kogyo Kk | 光重合性不飽和樹脂および該樹脂を含有する感光性樹脂組成物 |
JP2002363123A (ja) * | 2001-03-29 | 2002-12-18 | Kansai Research Institute | 光活性化合物および感光性樹脂組成物 |
JP4530565B2 (ja) * | 2001-03-29 | 2010-08-25 | 大阪瓦斯株式会社 | モノアクリレートフルオレン化合物、該化合物を含有する組成物、及びその硬化物 |
JP2003048922A (ja) * | 2001-08-06 | 2003-02-21 | Toagosei Co Ltd | 活性エネルギー線硬化型樹脂シート形成剤 |
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