JP5713477B2 - 光活性化合物およびこれを含む感光性樹脂組成物 - Google Patents
光活性化合物およびこれを含む感光性樹脂組成物 Download PDFInfo
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- JP5713477B2 JP5713477B2 JP2014505096A JP2014505096A JP5713477B2 JP 5713477 B2 JP5713477 B2 JP 5713477B2 JP 2014505096 A JP2014505096 A JP 2014505096A JP 2014505096 A JP2014505096 A JP 2014505096A JP 5713477 B2 JP5713477 B2 JP 5713477B2
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- photosensitive resin
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- 150000001875 compounds Chemical class 0.000 title claims description 113
- 239000011342 resin composition Substances 0.000 title claims description 98
- 239000000126 substance Substances 0.000 claims description 30
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- 239000011347 resin Substances 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000000049 pigment Substances 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 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
- 239000004094 surface-active agent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
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- 238000012719 thermal polymerization Methods 0.000 claims description 3
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 57
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
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- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KVIUXRJCBBXEGJ-UHFFFAOYSA-N 2,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1 KVIUXRJCBBXEGJ-UHFFFAOYSA-N 0.000 description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Images
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Description
本発明では、オキシムエステルを基本構造として含む光活性化合物において、ニトロ基とホスホネート基を置換基として必須に含むように光活性化合物の構造を変更することにより、UV光源に対する吸収率が高く、かかる光活性化合物が感光性樹脂組成物で光重合開始剤として使用される時、バインダー樹脂との相溶性に優れて溶解度が改善され、感度に優れ、高温での工程特性に優れていることを確認することができた。
本発明の一実施形態にかかる感光性樹脂組成物は、前記化学式1で表される光活性化合物を光重合開始剤として使用し、これにアルカリ可溶性バインダー樹脂、エチレン性不飽和結合を有する重合性化合物、および溶媒を含む。
合成例1の(4)ステップにおいて、2−メトキシベンゾイルクロリドの代わりに、4−メトキシベンゾイルクロリドgを使用したことを除いては、同様の方法で反応させて前記化学式2で表される光活性化合物を得た。下記化学式2で表される光活性化合物の1H−NMRを用いた測定結果は、次のとおりである。
合成例1の(4)ステップにおいて、2−メトキシベンゾイルクロリドの代わりに、2−エトキシベンゾイルクロリドgを使用したことを除いては、同様の方法で反応させて前記化学式3で表される光活性化合物を得た。下記化学式3で表される光活性化合物の1H−NMRを用いた測定結果は、次のとおりである。
合成例1の(4)ステップにおいて、2−メトキシベンゾイルクロリドの代わりに、2,4−ジメトキシベンゾイルクロリドgを使用したことを除いては、同様の方法で反応させて下記化学式4で表される光活性化合物を得た。下記化学式4で表される光活性化合物の1H−NMRを用いた測定結果は、次のとおりである。
合成例1の(4)ステップにおいて、2−メトキシベンゾイルクロリドの代わりに、2,4−ジメトキシベンゾイルクロリドgを使用したことを除いては、同様の方法で反応させて下記化学式5で表される光活性化合物を得た。下記化学式5で表される光活性化合物の1H−NMRを用いた測定結果は、次のとおりである。
合成例1の(4)ステップにおいて、2−メトキシベンゾイルクロリドの代わりに、2,4−ジメトキシベンゾイルクロリドgを使用したことを除いては、同様の方法で反応させて下記化学式6で表される光活性化合物を得た。下記化学式6で表される光活性化合物の1H−NMRを用いた測定結果は、次のとおりである。
ベンジルメタクリレート/メタアクリル酸(BzMA/MAA)(モル比:70/30、Mw:10,000、酸価115KOH mg/g)の共重合体のアルカリ可溶性バインダー樹脂10g、エチレン性不飽和結合を有する重合性化合物のジペンタエリスリトールヘキサアクリレート17g、接着助剤のKBM−503 0.3g、界面活性剤のBYK−331 0.06g、次の表1に示された、前記合成例1で製造された光活性化合物(1)0.6gと、有機溶媒のPGMEA72.04gを、シェーカーを用いて3時間混合させ、感光性樹脂組成物溶液を得た。
光活性化合物として、次の表1の化合物(1)の代わりに、前記合成例4で得られた化合物(4)を0.6g使用したことを除いては、前記実施例1と同様の方法で感光性樹脂組成物を製造した。
光活性化合物として、次の表1の化合物(1)の代わりに、前記合成例5で得られた化合物(5)を0.6g使用したことを除いては、前記実施例1と同様の方法で感光性樹脂組成物を製造した。
光活性化合物として、次の表1の化合物(1)の代わりに、前記合成例6で得られた化合物(6)を0.6g使用したことを除いては、前記実施例7と同様の方法で感光性樹脂組成物を製造した。
光活性化合物として、前記表1の化合物(1)の代わりに、化合物(7)のIrgacure OXE−02(BASF社)0.6gを使用したことを除いては、前記実施例1と同様の方法で感光性樹脂組成物を製造した。
前記実施例1〜4と比較例で製造した透明な感光性樹脂組成物を、ガラスにスピンコーティングした後、約110℃に70秒間前熱処理し、厚さが約3.7μmの均等なフィルムを形成した。前記フィルムを、直径14μmの円形の独立パターン(Isolated Pattern)型フォトマスクを用い、高圧水銀ランプ下、40mJ/cm2の露光量で露光させた後、パターンをpH11.3〜11.9のKOHアルカリ水溶液で現像し、脱イオン水で洗浄した。これを230℃で約20分間後熱処理した後、パターンの物性を下記のような方法で測定し、その結果を次の表2に示した。
実施例と比較例において、40mJ/cm2の同一露光量で製造されたパターンを、パターンプロファイラで大きさを測定し、下部10%に相当する部分の直径を下部CDで表した。同一露光量で露光を進行したので、光開始効率の良い開始剤を使用した組成物の方で、露光時に架橋がより良く進行してより大きいパターンを形成するため、CD値が大きいほど感度に優れるといえる。
実施例と比較例において、40mJ/cm2の同一露光量で製造されたパターンを、パターンプロファイラで大きさを測定し、上部5%に相当する部分の直径を上部CDで表した。同一露光量で露光を進行したので、光開始効率の良い開始剤を使用した組成物の方で、露光時に架橋がより良く進行してより大きいパターンを形成するため、CD値が大きいほど感度に優れるといえる。
カーボン分散液95g(カーボンの含有量が20重量%含まれる)、アルカリ可溶性カルド系バインダー{アクリル酸の付加されたビスフェノールフルオレンエポキシアクリレート/1,3−シクロヘキシルジイソシアネート(モル比65/35、Mw=5000、酸価80KOH mg/g)}5g、アルカリ可溶性アクリル系バインダー{ベンジルメタアクリレート/N−フェニルマレイミド/スチレン/メタアクリル酸(モル比60/10/12/18、Mw=15000、80KOH mg/g)}3g、エチレン性不飽和結合を有する重合性化合物のジペンタエリスリトールヘキサアクリレート3g、光活性化合物として合成例1で合成した化合物(1)2.5g、接着助剤のKBM−503 0.5gおよび界面活性剤のF−475(DIC社)0.1g、溶媒としてPGMEA164.5gを、シェーカーを用いて5時間混合させ、着色感光性樹脂組成物溶液を得た。
光活性化合物として、合成例1で合成した化合物(1)の代わりに、前記合成例2で得られた化合物(2)を2.5g使用したことを除いては、前記実施例5と同様の方法で着色感光性樹脂組成物を製造した。
光活性化合物として、合成例1で合成した化合物(1)の代わりに、前記合成例3で得られた化合物(3)を2.5g使用したことを除いては、前記実施例5と同様の方法で着色感光性樹脂組成物を製造した。
光活性化合物として、前記表1の化合物(1)の代わりに、化合物(7)のIrgacure OXE−02(BASF社)2.5gを使用したことを除いては、前記実施例5と同様の方法で着色感光性樹脂組成物を製造した。
光活性化合物として、合成例1で合成した化合物(1)の代わりに、前記表1の化合物(8)2.5gを使用したことを除いては、前記実施例5と同様の方法で着色感光性樹脂組成物を製造した。
光活性化合物として、合成例1で合成した化合物(1)の代わりに、前記表1の化合物(9)2.5gを使用したことを除いては、前記実施例5と同様の方法で着色感光性樹脂組成物を製造した。
前記実施例5〜7と比較例3、4で製造された着色感光性樹脂組成物を、ガラスにスピンコーティングした後、約100℃に100秒間前熱処理し、約1.3μm厚さの塗膜を形成した。その後、室温で冷却した後、線幅10μmの線状パターン(Line Pattern)型フォトマスクを用い、高圧水銀ランプ下、50mJ/cm2の露光量で露光させた。前記露光した基板を、25℃の温度にて0.04%のKOH水溶液でスプレー方式によって50秒間現像した後、純水で洗浄して乾燥させ、230℃のコンベクションオーブンで30分間ポストベーク(post−bake)した。生成されたパターンの物性を下記のような方法で測定し、その結果を次の表3に示した。
現像後、パターンが良好に形成できた場合O、現像性が低下してパターンがきれいに生成されずに直進性が低下した場合をXで表した。
実施例と比較例で50mJ/cm2の同一露光量で製造されたパターンを、SEMで大きさを測定し、下部の線幅をパターンCDで表した。同一露光量で露光を進行したので、光開始効率の良い開始剤を使用した組成物の方で、露光時に架橋がより良く進行してより大きいパターンを形成するため、CD値が大きいほど感度に優れるといえる。
Claims (20)
- 下記化学式1で表される光活性化合物。
[化学式1]
R1は、C1〜C8のアルキル基またはC6〜C12のアリール基であり、
R2は、C1〜C8のアルキル基またはR、OR、SRおよびCORからなる群より選択される1つ以上の置換基で置換されたC1〜C8のアルキル基であり、
R3およびR4は、水素または互いに連結されて縮合環を形成し、
R5は、C1〜C8のアルキル基またはC6〜C12のアリール基であり、
Aは、C2〜C15のアルキレン基またはR、OR、SR、CORおよびOCORからなる群より選択される1つ以上の置換基で置換されたC2〜C15のアルキレン基であり、
Rは、C1〜C10のアルキル基、C1〜C10のハロアルキル基またはC7〜C13のアラルキル基から選択される。 - 前記化学式1において、前記R1は、メチル基またはフェニル基であり、前記R2は、エチル基またはメチル基であり、前記R5は、メチル基またはエチル基であり、前記Aは、へキシレン基またはプロピレン基であることを特徴とする、
請求項1に記載の光活性化合物。 - a)下記化学式1で表される光活性化合物と、
b)アルカリ可溶性バインダー樹脂と、
c)エチレン性不飽和結合を有する重合性化合物と、
d)溶媒と
を含む感光性樹脂組成物。
[化学式1]
R1は、C1〜C8のアルキル基またはC6〜C12のアリール基であり、
R2は、C1〜C8のアルキル基またはR、OR、SRおよびCORからなる群より選択される1つ以上の置換基で置換されたC1〜C8のアルキル基であり、
R3およびR4は、水素または互いに連結されて縮合環を形成し、
R5は、C1〜C8のアルキル基またはC6〜C12のアリール基であり、
Aは、C2〜C15のアルキレン基またはR、OR、SR、CORおよびOCORからなる群より選択される1つ以上の置換基で置換されたC2〜C15のアルキレン基であり、
Rは、C1〜C10のアルキル基C1〜C10のハロアルキル基またはC7〜C13のアラルキル基から選択される。 - 前記R1は、メチル基またはフェニル基であり、前記R2は、エチル基またはメチル基であり、前記R5は、メチル基またはエチル基であり、前記Aは、へキシレン基またはプロピレン基であることを特徴とする、
請求項3に記載の感光性樹脂組成物。 - 前記アルカリ可溶性バインダー樹脂は、酸価30〜300KOH mg/gであることを特徴とする、
請求項3または4に記載の感光性樹脂組成物。 - 前記アルカリ可溶性バインダー樹脂は、重量平均分子量が1,000〜200,000であることを特徴とする、
請求項3から5のいずれか1項に記載の感光性樹脂組成物。 - 前記化学式1において、光活性化合物の含有量は、感光性樹脂組成物の総重量を基準として0.1〜5重量%であることを特徴とする、
請求項3から6のいずれか1項に記載の感光性樹脂組成物。 - 前記アルカリ可溶性バインダー樹脂の含有量は、感光性樹脂組成物の総重量を基準として1〜30重量%であることを特徴とする、
請求項3から7のいずれか1項に記載の感光性樹脂組成物。 - 前記エチレン性不飽和結合を有する重合性化合物の含有量は、感光性樹脂組成物の総重量を基準として0.5〜30重量%であることを特徴とする、
請求項3から8のいずれか1項に記載の感光性樹脂組成物。 - 前記溶媒の含有量は、感光性樹脂組成物の総重量を基準として40〜95重量%であることを特徴とする、
請求項3から9のいずれか1項に記載の感光性樹脂組成物。 - 前記感光性樹脂組成物は、着色剤をさらに含むことを特徴とする、
請求項3から10のいずれか1項に記載の感光性樹脂組成物。 - 前記着色剤は、感光性樹脂組成物の総重量を基準として1〜20重量%で含まれることを特徴とする、
請求項11記載の感光性樹脂組成物。 - 前記感光性樹脂組成物は、第2の光活性化合物をさらに含むことを特徴とする、
請求項3から12のいずれか1項に記載の感光性樹脂組成物。 - 前記第2の光活性化合物は、感光性樹脂組成物の総重量を基準として0.1〜5重量%で含まれることを特徴とする、
請求項13に記載の感光性樹脂組成物。 - 前記感光性樹脂組成物は、硬化促進剤、熱重合抑制剤、分散剤、酸化防止剤、紫外線吸収剤、レベリング剤、光増減剤、可塑剤、接着促進剤、充填剤および界面活性剤からなる群より選択される1つまたは2つ以上の添加剤をさらに含むことを特徴とする、
請求項3から14のいずれか1項に記載の感光性樹脂組成物。 - 前記添加剤は、感光性樹脂組成物の総重量を基準としてそれぞれ0.01〜5重量%含まれることを特徴とする、
請求項15に記載の感光性樹脂組成物。 - 請求項3から16のいずれか1項に記載の感光性樹脂組成物を用いて製造された感光材。
- 請求項3から16のいずれか1項に記載の感光性樹脂組成物の硬化物を含む感光材。
- 前記感光材は、TFT LCDカラーフィルタ製造用顔料分散型感光材、TFT LCDまたは有機発光ダイオードのブラックマトリックス形成用感光材、オーバーコート層形成用感光材、カラムスペーサ感光材および印刷配線盤用感光材からなる群より選択されることを特徴とする、
請求項17又は請求項18に記載の感光材。 - 請求項17から請求項19までの何れか一項に記載の感光材を含む電子素子。
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