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 PDF

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Publication number: JP6408715B2
Authority: JP; Japan
Prior art keywords: diethyl; bis; reaction; fluoren; fluorene
Prior art date: 2015-02-06
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.): Active

Application number

JP2017541678A

Other languages

English (en)

Japanese (ja)

Other versions

JP2018506532A (ja

Inventor

チュンリムオ

スンリムシン

ジョンイルシン

キュンリョンアン

クンジュン

ドゥク−ラクイ

ヨン−イルチョ

ミンスンイ

ウォン−ジュンイ

ジェ−フンイ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Samyang Corp

Original Assignee

Samyang Corp

Priority date (The priority date 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 date listed.)

2015-02-06

Filing date

2016-02-02

Publication date

2018-10-17

2015-02-06 Priority claimed from KR1020150018698A external-priority patent/KR101828927B1/ko

2015-04-09 Priority claimed from KR1020150050017A external-priority patent/KR101824443B1/ko

2016-02-02 Application filed by Samyang Corp filed Critical Samyang Corp

2018-03-08 Publication of JP2018506532A publication Critical patent/JP2018506532A/ja

2018-10-17 Application granted granted Critical

2018-10-17 Publication of JP6408715B2 publication Critical patent/JP6408715B2/ja

Status Active legal-status Critical Current

2036-02-02 Anticipated expiration legal-status Critical

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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
238000011161 development Methods 0.000 description 7
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239000011159 matrix material Substances 0.000 description 7
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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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
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
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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
239000007864 aqueous solution Substances 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 5
239000011521 glass Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
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FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 4
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
YRICEVWLDWBSHG-UHFFFAOYSA-N N-[4-(9,9-diethylfluoren-2-yl)-4-hydroxyimino-3-methylbutan-2-ylidene]hydroxylamine Chemical compound C(C)C1(C2=CC=CC=C2C=2C=CC(=CC1=2)C(C(C(C)=NO)C)=NO)CC YRICEVWLDWBSHG-UHFFFAOYSA-N 0.000 description 4
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DNPZTOSITLBUKV-UHFFFAOYSA-N [1-[7-(N-acetyloxy-C-hexylcarbonimidoyl)-9,9-diethylfluoren-2-yl]propylideneamino] acetate Chemical compound C(C)(=O)ON=C(CCCCCC)C1=CC=2C(C3=CC(=CC=C3C2C=C1)C(CC)=NOC(C)=O)(CC)CC DNPZTOSITLBUKV-UHFFFAOYSA-N 0.000 description 4
VZPLQUOFHILBCV-UHFFFAOYSA-N [1-[7-(N-benzoyloxy-C-hexylcarbonimidoyl)-9,9-diethylfluoren-2-yl]propylideneamino] benzoate Chemical compound C(C1=CC=CC=C1)(=O)ON=C(CCCCCC)C1=CC=2C(C3=CC(=CC=C3C2C=C1)C(CC)=NOC(C1=CC=CC=C1)=O)(CC)CC VZPLQUOFHILBCV-UHFFFAOYSA-N 0.000 description 4
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
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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
235000017281 sodium acetate Nutrition 0.000 description 4
125000006850 spacer group Chemical group 0.000 description 4
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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

- 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

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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)

JP2017541678A 2015-02-06 2016-02-02 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 Active JP6408715B2 (ja)

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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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KR101840584B1 (ko) *	2017-01-17	2018-03-20	동우 화인켐 주식회사	착색 감광성 수지 조성물, 컬러필터 및 화상표시장치
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KR20200135308A (ko) *	2018-03-27	2020-12-02	가부시키가이샤 아데카	화합물, 라디칼 중합 개시제, 조성물, 경화물 및 경화물의 제조 방법
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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
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