JP6408715B2 - 新規のオキシムエステル誘導体化合物およびこれを含む光重合開始剤、ならびにフォトレジスト組成物 - Google Patents
新規のオキシムエステル誘導体化合物およびこれを含む光重合開始剤、ならびにフォトレジスト組成物 Download PDFInfo
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- JP6408715B2 JP6408715B2 JP2017541678A JP2017541678A JP6408715B2 JP 6408715 B2 JP6408715 B2 JP 6408715B2 JP 2017541678 A JP2017541678 A JP 2017541678A JP 2017541678 A JP2017541678 A JP 2017541678A JP 6408715 B2 JP6408715 B2 JP 6408715B2
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- Prior art keywords
- diethyl
- bis
- reaction
- fluoren
- fluorene
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- -1 oxime ester Chemical class 0.000 title claims description 129
- 239000000203 mixture Substances 0.000 title claims description 88
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 78
- 150000001875 compounds Chemical class 0.000 title claims description 48
- 239000003999 initiator Substances 0.000 title description 23
- 239000000126 substance Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims 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 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004851 cyclopentylmethyl group Chemical class C1(CCCC1)C* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical class [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000001125 extrusion Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 152
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 73
- 230000015572 biosynthetic process Effects 0.000 description 59
- 238000003786 synthesis reaction Methods 0.000 description 58
- 229910052760 oxygen Inorganic materials 0.000 description 50
- 238000005160 1H NMR spectroscopy Methods 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 44
- 239000012044 organic layer Substances 0.000 description 42
- 150000002923 oximes Chemical class 0.000 description 41
- 238000004519 manufacturing process Methods 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 238000005481 NMR spectroscopy Methods 0.000 description 35
- 239000007795 chemical reaction product Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000012153 distilled water Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 22
- 239000012346 acetyl chloride Substances 0.000 description 22
- 239000010408 film Substances 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- DXLHOCYBTWOELM-UHFFFAOYSA-N 9,9-diethylfluorene Chemical compound C1=CC=C2C(CC)(CC)C3=CC=CC=C3C2=C1 DXLHOCYBTWOELM-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 230000035945 sensitivity Effects 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 12
- DMPRGALJZHJXPN-UHFFFAOYSA-N N-[4-(9,9-diethylfluoren-2-yl)-4-hydroxyiminobutan-2-ylidene]hydroxylamine Chemical compound C(C)C1(C2=CC=CC=C2C=2C=CC(=CC1=2)C(CC(C)=NO)=NO)CC DMPRGALJZHJXPN-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 229920000058 polyacrylate Polymers 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- XLRWHLUJCNRMCM-UHFFFAOYSA-N CCCCC1(CCCC)c2cc(ccc2-c2ccc(cc12)[N+]([O-])=O)C(C)=O Chemical compound CCCCC1(CCCC)c2cc(ccc2-c2ccc(cc12)[N+]([O-])=O)C(C)=O XLRWHLUJCNRMCM-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 8
- UZDMKAOAYMEASM-UHFFFAOYSA-N 1-(9,9-diethylfluoren-2-yl)butane-1,3-dione Chemical compound C(C)C1(C2=CC=CC=C2C=2C=CC(=CC1=2)C(CC(C)=O)=O)CC UZDMKAOAYMEASM-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- VLBYUEUKIQSWPN-UHFFFAOYSA-N N-[5-(9,9-diethylfluoren-2-yl)-5-hydroxyiminopentan-2-ylidene]hydroxylamine Chemical compound C(C)C1(C2=CC=CC=C2C=2C=CC(=CC1=2)C(CCC(C)=NO)=NO)CC VLBYUEUKIQSWPN-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- GUKGUSRXNUKOMV-UHFFFAOYSA-N 1-(9,9-dibutyl-7-nitrofluoren-2-yl)butane-1,3-dione Chemical compound C(CCC)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C(CC(C)=O)=O)[N+](=O)[O-])CCCC GUKGUSRXNUKOMV-UHFFFAOYSA-N 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- VCPWFFATCCGJFR-UHFFFAOYSA-N 9,9-dibutyl-2-nitrofluorene Chemical compound C1=C([N+]([O-])=O)C=C2C(CCCC)(CCCC)C3=CC=CC=C3C2=C1 VCPWFFATCCGJFR-UHFFFAOYSA-N 0.000 description 6
- BOCNMKNSLVBIDK-UHFFFAOYSA-N 9,9-diethyl-4-nitrofluorene Chemical compound C(C)C1(C2=CC=CC=C2C=2C(=CC=CC1=2)[N+](=O)[O-])CC BOCNMKNSLVBIDK-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- ZCLOVVCFWRNGAH-UHFFFAOYSA-N N-[1-[9,9-diethyl-7-(C-ethyl-N-hydroxycarbonimidoyl)fluoren-2-yl]heptylidene]hydroxylamine Chemical compound C(C)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C(CCCCCC)=NO)C(CC)=NO)CC ZCLOVVCFWRNGAH-UHFFFAOYSA-N 0.000 description 6
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- PHRUXNKZILIWFR-UHFFFAOYSA-N 1-(7-bromo-9,9-dibutylfluoren-2-yl)butane-1,3-dione Chemical compound BrC1=CC=C2C=3C=CC(=CC=3C(C2=C1)(CCCC)CCCC)C(CC(C)=O)=O PHRUXNKZILIWFR-UHFFFAOYSA-N 0.000 description 5
- VWLCVVPVYQCGSH-UHFFFAOYSA-N 1-(9,9-dibutyl-7-phenylfluoren-2-yl)butane-1,3-dione Chemical compound C(CCC)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C(CC(C)=O)=O)C1=CC=CC=C1)CCCC VWLCVVPVYQCGSH-UHFFFAOYSA-N 0.000 description 5
- RYVRLBHKGNRXTE-UHFFFAOYSA-N 1-(9,9-diethylfluoren-2-yl)propan-1-one Chemical compound C(C)C1(C2=CC=CC=C2C=2C=CC(=CC12)C(CC)=O)CC RYVRLBHKGNRXTE-UHFFFAOYSA-N 0.000 description 5
- TUAZQZXFKMWXHI-UHFFFAOYSA-N C(C)C1(C2=CC=CC=C2C=2C=CC(=CC1=2)C(C(C(C)=O)C)=O)CC Chemical compound C(C)C1(C2=CC=CC=C2C=2C=CC(=CC1=2)C(C(C(C)=O)C)=O)CC TUAZQZXFKMWXHI-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
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- UWXQLPWAZXTQEZ-UHFFFAOYSA-N 4-bromo-9,9-diethylfluorene Chemical compound BrC1=CC=CC=2C(C3=CC=CC=C3C1=2)(CC)CC UWXQLPWAZXTQEZ-UHFFFAOYSA-N 0.000 description 4
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- HZGMFVCYHFDNGW-UHFFFAOYSA-N 9h-fluorene-2-carbonitrile Chemical compound C1=CC=C2C3=CC=C(C#N)C=C3CC2=C1 HZGMFVCYHFDNGW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZJALHGPCWBNAIV-UHFFFAOYSA-N N-[4-(9,9-dibutyl-7-nitrofluoren-2-yl)-4-hydroxyiminobutan-2-ylidene]hydroxylamine Chemical compound C(CCC)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C(CC(C)=NO)=NO)[N+](=O)[O-])CCCC ZJALHGPCWBNAIV-UHFFFAOYSA-N 0.000 description 4
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- VRKDACZPMHFUAE-UHFFFAOYSA-N [1-[7-[N-(cyclohexanecarbonyloxy)-C-hexylcarbonimidoyl]-9,9-diethylfluoren-2-yl]propylideneamino] cyclohexanecarboxylate Chemical compound CCCCCCC(=NOC(=O)C1CCCCC1)C2=CC3=C(C=C2)C4=C(C3(CC)CC)C=C(C=C4)C(=NOC(=O)C5CCCCC5)CC VRKDACZPMHFUAE-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
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- 125000006850 spacer group Chemical group 0.000 description 4
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/68—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with at least one of the esterifying carboxyl groups bound to a carbon atom of a six-membered aromatic ring
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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KR10-2015-0018698 | 2015-02-06 | ||
KR1020150018698A KR101828927B1 (ko) | 2015-02-06 | 2015-02-06 | 신규한 옥심에스테르 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
KR10-2015-0050017 | 2015-04-09 | ||
KR1020150050017A KR101824443B1 (ko) | 2015-04-09 | 2015-04-09 | 신규한 플루오렌일 옥심 에스테르 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
PCT/KR2016/001103 WO2016126070A1 (ko) | 2015-02-06 | 2016-02-02 | 신규한 옥심에스테르 유도체 화합물 및 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
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JP (1) | JP6408715B2 (ko) |
CN (1) | CN107250105B (ko) |
TW (1) | TWI682921B (ko) |
WO (1) | WO2016126070A1 (ko) |
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KR101834209B1 (ko) * | 2016-11-25 | 2018-03-06 | 주식회사 삼양사 | 광중합 개시제 및 이를 포함하는 차광용 감광성 수지 조성물 |
KR101840584B1 (ko) * | 2017-01-17 | 2018-03-20 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러필터 및 화상표시장치 |
CN106831487B (zh) * | 2017-01-22 | 2018-12-07 | 苏州楚凯药业有限公司 | 有机电子产品中间体芴类衍生物的制备方法 |
JP7032416B2 (ja) * | 2017-02-17 | 2022-03-08 | 常州強力先端電子材料有限公司 | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
JP7051321B2 (ja) * | 2017-07-21 | 2022-04-11 | 東京応化工業株式会社 | 感光性組成物、パターン形成方法、硬化物、及び表示装置 |
CN107445861A (zh) * | 2017-08-04 | 2017-12-08 | 吴赣药业(苏州)有限公司 | 一种2‑硝基‑7‑乙酰肟基‑9,9‑二丁基芴的制备方法 |
KR20200135308A (ko) * | 2018-03-27 | 2020-12-02 | 가부시키가이샤 아데카 | 화합물, 라디칼 중합 개시제, 조성물, 경화물 및 경화물의 제조 방법 |
JP7460288B2 (ja) * | 2018-08-07 | 2024-04-02 | 株式会社Adeka | カルバモイルオキシム化合物並びに該化合物を含有する重合開始剤及び重合性組成物 |
CN112010788B (zh) * | 2019-05-31 | 2022-10-21 | 常州强力先端电子材料有限公司 | 一种非离子型肟酯类光产酸剂 |
CN110668971A (zh) * | 2019-10-24 | 2020-01-10 | 重庆沃肯精细化工有限公司 | 一种不对称芴肟酯化合物及其制备方法和光敏性组合物 |
CN112851547B (zh) * | 2019-11-12 | 2024-06-07 | 常州强力先端电子材料有限公司 | 芴肟酯类化合物及其制备方法、感光性树脂组合物 |
JP2021167905A (ja) * | 2020-04-10 | 2021-10-21 | 東京応化工業株式会社 | 感光性組成物、パターン化された硬化膜の製造方法、及びパターン化された硬化膜 |
JP2021167906A (ja) * | 2020-04-10 | 2021-10-21 | 東京応化工業株式会社 | 感光性組成物、パターン化された硬化膜の製造方法、及びパターン化された硬化膜 |
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KR100523295B1 (ko) * | 2003-01-10 | 2005-10-24 | 한국화학연구원 | 광중합성 조성물 및 이로부터 제조된 광중합성 막 |
JP2010156879A (ja) * | 2008-12-29 | 2010-07-15 | Fujifilm Corp | 感光性組成物、カラーフィルタ、及び液晶表示装置 |
WO2013165207A1 (ko) * | 2012-05-03 | 2013-11-07 | 한국화학연구원 | 신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
JP5682094B2 (ja) * | 2012-09-28 | 2015-03-11 | ダイトーケミックス株式会社 | フルオレン系化合物、該フルオレン系化合物を含む光重合開始剤、および、該光重合開始剤を含む感光性組成物 |
JP6065596B2 (ja) * | 2013-01-16 | 2017-01-25 | Jsr株式会社 | 感放射線性着色組成物、着色硬化膜及び表示素子 |
KR101567837B1 (ko) * | 2013-06-11 | 2015-11-11 | 애경화학 주식회사 | 플루오렌 구조를 갖는 신규한 광개시제 및 이를 포함하는 반응성 액정 조성물 및 감광성 조성물 |
JP2015011095A (ja) * | 2013-06-27 | 2015-01-19 | 凸版印刷株式会社 | フォトスペーサー形成用感光性樹脂組成物及びカラーフィルタ |
KR101435652B1 (ko) * | 2014-01-17 | 2014-08-28 | 주식회사 삼양사 | 신규한 β-옥심에스테르 플루오렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
CN103819583B (zh) * | 2014-03-18 | 2016-05-18 | 常州强力电子新材料股份有限公司 | 一种含硝基双肟酯类光引发剂及其制备方法和应用 |
CN103833872B (zh) * | 2014-03-18 | 2016-04-06 | 常州强力先端电子材料有限公司 | 一种双肟酯类光引发剂及其制备方法和应用 |
CN104076606B (zh) * | 2014-07-15 | 2019-12-03 | 常州强力电子新材料股份有限公司 | 一种含肟酯类光引发剂的感光性组合物及其应用 |
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- 2016-02-02 WO PCT/KR2016/001103 patent/WO2016126070A1/ko active Application Filing
- 2016-02-02 CN CN201680008616.0A patent/CN107250105B/zh active Active
- 2016-02-04 TW TW105103739A patent/TWI682921B/zh active
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CN107250105B (zh) | 2019-08-20 |
TW201634444A (zh) | 2016-10-01 |
WO2016126070A1 (ko) | 2016-08-11 |
TWI682921B (zh) | 2020-01-21 |
JP2018506532A (ja) | 2018-03-08 |
CN107250105A (zh) | 2017-10-13 |
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