JP5890337B2 - Radiation-sensitive resin composition, insulating film, and display device - Google Patents
Radiation-sensitive resin composition, insulating film, and display device Download PDFInfo
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- JP5890337B2 JP5890337B2 JP2013026082A JP2013026082A JP5890337B2 JP 5890337 B2 JP5890337 B2 JP 5890337B2 JP 2013026082 A JP2013026082 A JP 2013026082A JP 2013026082 A JP2013026082 A JP 2013026082A JP 5890337 B2 JP5890337 B2 JP 5890337B2
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- 230000005855 radiation Effects 0.000 title claims description 89
- 239000011342 resin composition Substances 0.000 title claims description 78
- -1 naphthoxy group Chemical group 0.000 claims description 162
- 125000001424 substituent group Chemical group 0.000 claims description 104
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 53
- 229920005989 resin Polymers 0.000 claims description 49
- 239000011347 resin Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000000962 organic group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 239000003999 initiator Substances 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 24
- 125000002723 alicyclic group Chemical group 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000003700 epoxy group Chemical group 0.000 claims description 15
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 9
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 9
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 101100116570 Caenorhabditis elegans cup-2 gene Proteins 0.000 claims 1
- 101100116572 Drosophila melanogaster Der-1 gene Proteins 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
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- 238000000034 method Methods 0.000 description 15
- 238000011161 development Methods 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
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- 230000000052 comparative effect Effects 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 230000001771 impaired effect Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- 238000011156 evaluation Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 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
- 230000035945 sensitivity Effects 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 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 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 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 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
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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 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
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- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- 0 Cc(cccc1)c1C(C(I)=O)=NOC* Chemical compound Cc(cccc1)c1C(C(I)=O)=NOC* 0.000 description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- 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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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
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- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
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- YMQHXFNDANLQTI-UHFFFAOYSA-N ethenyl 2,3,4,5-tetrachlorobenzoate Chemical compound ClC1=CC(C(=O)OC=C)=C(Cl)C(Cl)=C1Cl YMQHXFNDANLQTI-UHFFFAOYSA-N 0.000 description 1
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- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000006608 n-octyloxy group Chemical group 0.000 description 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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- 238000006146 oximation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
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- HAFZJTKIBGEQKT-UHFFFAOYSA-N prop-2-enyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC=C HAFZJTKIBGEQKT-UHFFFAOYSA-N 0.000 description 1
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- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
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- 239000007870 radical polymerization initiator Substances 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
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Classifications
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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- 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
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- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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Description
本発明は、感放射線性樹脂組成物、当該感放射線性樹脂組成物を用いて形成される絶縁膜、及び当該絶縁膜を備える表示装置に関する。 The present invention relates to a radiation-sensitive resin composition, an insulating film formed using the radiation-sensitive resin composition, and a display device including the insulating film.
液晶表示装置のような表示装置では、絶縁膜や、スペーサーのような材料が、バックライトのような光源から発せられる光を効率よく透過させる必要がある。このため、絶縁膜やスペーサーのパターンを形成するために、露光により透明な硬化膜を与える感放射線性樹脂組成物(感光性樹脂組成物)が用いられる。このような、感放射線性樹脂組成物を選択的に露光することにより、透明な硬化膜のパターンを形成できる。 In a display device such as a liquid crystal display device, an insulating film or a material such as a spacer needs to efficiently transmit light emitted from a light source such as a backlight. For this reason, in order to form the pattern of an insulating film or a spacer, the radiation sensitive resin composition (photosensitive resin composition) which gives a transparent cured film by exposure is used. By selectively exposing such a radiation sensitive resin composition, a transparent cured film pattern can be formed.
透明な硬化膜を形成可能な感放射線性樹脂組成物(感光性樹脂組成物)としては、例えば、樹脂と、重合性化合物と、特定の構造の重合開始剤と、溶剤とを含む組成物が提案されている(特許文献1)。具体的には、特許文献1の実施例には、メタクリル酸と脂環式エポキシ基を有するアクリレートとの共重合体と、ジペンタエリスリトールヘキサアクリレートと、下式で表される重合開始剤と、3−メトキシ−1−ブタノール、プロピレングリコールモノメチルエーテルアセテート、3−エトキシプロピオン酸エチル、及び3−メトキシブチルアセテートからなる混合溶剤と、を含む感放射線性樹脂組成物が開示されている。 Examples of the radiation sensitive resin composition (photosensitive resin composition) capable of forming a transparent cured film include a composition containing a resin, a polymerizable compound, a polymerization initiator having a specific structure, and a solvent. It has been proposed (Patent Document 1). Specifically, Examples of Patent Document 1 include a copolymer of methacrylic acid and an acrylate having an alicyclic epoxy group, dipentaerythritol hexaacrylate, a polymerization initiator represented by the following formula, A radiation-sensitive resin composition containing a mixed solvent composed of 3-methoxy-1-butanol, propylene glycol monomethyl ether acetate, ethyl 3-ethoxypropionate, and 3-methoxybutyl acetate is disclosed.
しかし、特許文献1に記載される感放射線性樹脂組成物を用いて形成される硬化膜は、透明性が十分でない。また、特許文献1に記載される感放射性樹脂組成物の塗膜を露光した後に、塗膜をテトラメチルアンモニウムヒドロキシドの水溶液のようなアルカリ現像液により現像する場合、残存すべき露光部が過度に溶解してしまい、所望する形状のパターンを形成しにくい。 However, the cured film formed using the radiation-sensitive resin composition described in Patent Document 1 is not sufficiently transparent. In addition, when the coating film of the radiation-sensitive resin composition described in Patent Document 1 is exposed and then developed with an alkali developer such as an aqueous solution of tetramethylammonium hydroxide, the exposed portion to be left is excessive. It is difficult to form a pattern having a desired shape.
本発明は、上記の課題に鑑みなされたものであって、透明性に優れる硬化膜を与え、露光後の現像時に露光部の過度の溶解が抑制される感放射線性樹脂組成物と、当該感放射線性樹脂組成物を用いて形成された絶縁膜と、当該絶縁膜を備える表示装置と、を提供することを目的とする。 The present invention has been made in view of the above problems, and provides a radiation-sensitive resin composition that gives a cured film having excellent transparency and suppresses excessive dissolution of an exposed portion during development after exposure, and the sensitivity. An object is to provide an insulating film formed using a radiation resin composition and a display device including the insulating film.
本発明者らは、感放射性樹脂組成物に、(a1)不飽和カルボン酸に由来する単位と、(a2)エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位と、を含む共重合体からなる(A)アルカリ可溶性樹脂と、(B)光重合性化合物と、特定の構造のオキシムエステル化合物を含む(C)光重合開始剤と、を配合することにより、上記の課題を解決できることを見出し、本発明を完成するに至った。 The inventors include (a1) a unit derived from an unsaturated carboxylic acid and (a2) a unit derived from an alicyclic skeleton-containing unsaturated compound having no epoxy group in the radiation-sensitive resin composition. By blending (A) an alkali-soluble resin made of a copolymer, (B) a photopolymerizable compound, and (C) a photopolymerization initiator containing an oxime ester compound having a specific structure, the above-mentioned problems are solved. The inventors have found that this can be solved, and have completed the present invention.
本発明の第一の態様は、(A)アルカリ可溶性樹脂、(B)光重合性化合物、(C)光重合開始剤を含み、
前記(A)アルカリ可溶性樹脂が、(a1)不飽和カルボン酸に由来する単位と、(a2)エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位と、を含み、
前記(C)光重合開始剤が、下記式(1):
で表されるオキシムエステル化合物を含む、感放射線性樹脂組成物である。
The first aspect of the present invention includes (A) an alkali-soluble resin, (B) a photopolymerizable compound, and (C) a photopolymerization initiator,
The (A) alkali-soluble resin comprises (a1) a unit derived from an unsaturated carboxylic acid and (a2) a unit derived from an alicyclic skeleton-containing unsaturated compound having no epoxy group,
The (C) photopolymerization initiator is represented by the following formula (1):
It is a radiation sensitive resin composition containing the oxime ester compound represented by these.
本発明の第二の態様は、第一の態様に係る感放射線性樹脂組成物を用いて形成された絶縁膜である。 The second aspect of the present invention is an insulating film formed using the radiation-sensitive resin composition according to the first aspect.
本発明の第三の態様は、第二の態様に係る絶縁膜を備える表示装置である。 A third aspect of the present invention is a display device including the insulating film according to the second aspect.
本発明によれば、透明性に優れる硬化膜を与え、露光後の現像時に露光部の過度の溶解が抑制される感放射線性樹脂組成物と、当該感放射線性樹脂組成物を用いて形成された絶縁膜と、当該絶縁膜を備える表示装置と、を提供することができる。 According to the present invention, a radiation-sensitive resin composition that gives a cured film having excellent transparency and suppresses excessive dissolution of an exposed area during development after exposure and the radiation-sensitive resin composition are formed. An insulating film and a display device including the insulating film can be provided.
≪感放射線性樹脂組成物≫
本発明に係る感放射線性樹脂組成物は、特定の単位を含む(A)アルカリ可溶性樹脂と、(B)光重合性化合物と、特定の構造のオキシムエステル化合物を含む(C)光重合開始剤と、を含有する。以下、感放射線性樹脂組成物に含有される各成分について説明する。
≪Radiosensitive resin composition≫
The radiation-sensitive resin composition according to the present invention includes (A) an alkali-soluble resin containing specific units, (B) a photopolymerizable compound, and (C) a photopolymerization initiator containing an oxime ester compound having a specific structure. And containing. Hereinafter, each component contained in the radiation sensitive resin composition will be described.
<(A)アルカリ可溶性樹脂>
(A)アルカリ可溶性樹脂とは、樹脂濃度20質量%の樹脂溶液(溶媒:プロピレングリコールモノメチルエーテルアセテート)により、膜厚1μmの樹脂膜を基板上に形成し、23℃で2.38質量%のテトラメチルアンモニウムヒドロキシド(TMAH)水溶液に1分間浸漬した際に、膜厚0.01μm以上溶解するものをいう。
<(A) Alkali-soluble resin>
(A) The alkali-soluble resin is a resin film having a resin concentration of 20% by mass (solvent: propylene glycol monomethyl ether acetate), and a resin film having a thickness of 1 μm is formed on the substrate, and 2.38% by mass at 23 ° C. When immersed in an aqueous tetramethylammonium hydroxide (TMAH) solution for 1 minute, it means a film that dissolves in a thickness of 0.01 μm or more.
(A)アルカリ可溶性樹脂としては、(a1)不飽和カルボン酸に由来する単位(以下、(a1)単位とも記す。)と、(a2)エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位(以下、(a2)単位とも記す。)と、を含む共重合体を用いる。(a1)単位と、(a2)単位とを含む(A)アルカリ可溶性樹脂を用いることで、透明性に優れる硬化膜を与え、露光後の現像時に露光部の過度の溶解が抑制される感放射線性樹脂組成物を得やすい。 (A) As an alkali-soluble resin, (a1) a unit derived from an unsaturated carboxylic acid (hereinafter also referred to as (a1) unit) and (a2) an alicyclic skeleton-containing unsaturated compound having no epoxy group A copolymer containing a derived unit (hereinafter also referred to as (a2) unit) is used. (A1) A radiation-sensitive material that provides a cured film having excellent transparency by using an alkali-soluble resin containing (a2) units and (a2) units, and that suppresses excessive dissolution of exposed areas during development after exposure. It is easy to obtain a functional resin composition.
(A)成分として用いる樹脂は、(a1)単位と、(a2)単位とを含むものであれば特に限定されず、従来から種々の感放射線性樹脂組成物において使用されていたアルカリ可溶性樹脂から、適宜選択して使用することができる。 The resin used as the component (A) is not particularly limited as long as it contains the (a1) unit and the (a2) unit. From the alkali-soluble resin conventionally used in various radiation-sensitive resin compositions. Can be appropriately selected and used.
(a1)単位を生成させる不飽和カルボン酸としては、(メタ)アクリル酸、クロトン酸等のモノカルボン酸;マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸等のジカルボン酸;これらジカルボン酸の無水物;等が挙げられる。これらの中でも、共重合反応性、得られる樹脂のアルカリ溶解性、入手の容易性等の点から、(メタ)アクリル酸及び無水マレイン酸が好ましい。(A)アルカリ可溶性樹脂は、これらの不飽和カルボン酸から誘導される(a1)単位を、2種以上組み合わせて含んでいてもよい。 (A1) Unsaturated carboxylic acids that generate units include monocarboxylic acids such as (meth) acrylic acid and crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid; these dicarboxylic acids Anhydrous anhydride; and the like. Among these, (meth) acrylic acid and maleic anhydride are preferable in terms of copolymerization reactivity, alkali solubility of the resulting resin, availability, and the like. (A) The alkali-soluble resin may contain a combination of two or more units (a1) derived from these unsaturated carboxylic acids.
(a2)単位は、エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位であれば特に限定されない。脂環式骨格は、単環であっても多環であってもよい。脂環式骨格含有不飽和化合物に含まれる単環の脂環式基としては、シクロペンチル基、シクロヘキシル基等が挙げられる。また、多環の脂環式基としては、アダマンチル基、ノルボルニル基、イソボルニル基、トリシクロノニル基、トリシクロデシル基、テトラシクロドデシル基等が挙げられる。(A)アルカリ可溶性樹脂は、(a2)単位を、2種以上組み合わせて含んでいてもよい。 The unit (a2) is not particularly limited as long as it is a unit derived from an alicyclic skeleton-containing unsaturated compound having no epoxy group. The alicyclic skeleton may be monocyclic or polycyclic. Examples of the monocyclic alicyclic group contained in the alicyclic skeleton-containing unsaturated compound include a cyclopentyl group and a cyclohexyl group. Examples of the polycyclic alicyclic group include an adamantyl group, a norbornyl group, an isobornyl group, a tricyclononyl group, a tricyclodecyl group, and a tetracyclododecyl group. (A) The alkali-soluble resin may contain a combination of two or more units (a2).
(a2)単位を与える、エポキシ基を持たない脂環式基含有不飽和化合物としては、例えば下記式(a2−1)〜(a2−7)で表される化合物が挙げられる。これらの中では、現像性の良好な感放射線性樹脂組成物を得やすいことから、下記式(a2−3)〜(a2−8)で表される化合物が好ましく、下記式(a2−3)又は(a2−4)で表される化合物がより好ましい。 (A2) As an alicyclic group containing unsaturated compound which does not have an epoxy group which gives a unit, the compound represented by following formula (a2-1)-(a2-7) is mentioned, for example. In these, since it is easy to obtain the radiation sensitive resin composition with favorable developability, the compounds represented by the following formulas (a2-3) to (a2-8) are preferable, and the following formula (a2-3) Or the compound represented by (a2-4) is more preferable.
上記式中、Ra1は水素原子又はメチル基を示し、Ra2は単結合又は炭素数1〜6の2価の脂肪族飽和炭化水素基を示し、Ra3は水素原子又は炭素数1〜5のアルキル基を示す。Ra2としては、単結合、直鎖状又は分枝鎖状のアルキレン基、例えばメチレン基、エチレン基、プロピレン基、テトラメチレン基、エチルエチレン基、ペンタメチレン基、ヘキサメチレン基が好ましい。Ra3としては、メチル基、エチル基が好ましい。 In the above formula, R a1 represents a hydrogen atom or a methyl group, R a2 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, and R a3 represents a hydrogen atom or 1 to 5 carbon atoms. Represents an alkyl group. R a2 is preferably a single bond or a linear or branched alkylene group such as a methylene group, an ethylene group, a propylene group, a tetramethylene group, an ethylethylene group, a pentamethylene group, or a hexamethylene group. R a3 is preferably a methyl group or an ethyl group.
また、(A)アルカリ可溶性樹脂は、(a1)単位及び(a2)単位に加え、(a3)脂環式エポキシ基含有不飽和化合物に由来する単位(以下、(a3)単位とも記す。)を含むのが好ましい。(A)アルカリ可溶性樹脂が、(a3)単位を含む場合、感放射線性樹脂組成物を用いて形成される塗布膜を露光後にポストベークする場合に、塗布膜の過度の形状変化を抑制しやすい。 In addition to (a1) unit and (a2) unit, (A) alkali-soluble resin includes (a3) a unit derived from an alicyclic epoxy group-containing unsaturated compound (hereinafter also referred to as (a3) unit). It is preferable to include. (A) When alkali-soluble resin contains (a3) unit, when the coating film formed using a radiation sensitive resin composition is post-baked after exposure, it is easy to suppress an excessive shape change of the coating film. .
(a3)単位において、脂環式エポキシ基を構成する脂環式基は、単環であっても多環であってもよい。単環の脂環式基としては、シクロペンチル基、シクロヘキシル基等が挙げられる。また、多環の脂環式基としては、ノルボルニル基、イソボルニル基、トリシクロノニル基、トリシクロデシル基、テトラシクロドデシル基等が挙げられる。(A)アルカリ可溶性樹脂は、(a3)単位を2種以上組み合わせて含んでいてもよい。 In the unit (a3), the alicyclic group constituting the alicyclic epoxy group may be monocyclic or polycyclic. Examples of the monocyclic alicyclic group include a cyclopentyl group and a cyclohexyl group. Examples of the polycyclic alicyclic group include a norbornyl group, an isobornyl group, a tricyclononyl group, a tricyclodecyl group, and a tetracyclododecyl group. (A) The alkali-soluble resin may contain a combination of two or more (a3) units.
(a3)単位を与える脂環式エポキシ基含有不飽和化合物の具体例としては、例えば下記式(a3−1)〜(a3−16)で表される化合物が挙げられる。これらの中でも、感放射性樹脂組成物の現像性を適度なものとするためには、下記式(a3−1)〜(a3−6)で表される化合物が好ましく、下記式(a3−1)〜(a3−4)で表される化合物がより好ましい。 (A3) Specific examples of the alicyclic epoxy group-containing unsaturated compound that gives a unit include compounds represented by the following formulas (a3-1) to (a3-16). Among these, the compounds represented by the following formulas (a3-1) to (a3-6) are preferable in order to make the developability of the radiation-sensitive resin composition appropriate, and the following formula (a3-1) The compound represented by (a3-4) is more preferable.
上記式中、Ra4は水素原子又はメチル基を示し、Ra5は炭素数1〜6の2価の脂肪族飽和炭化水素基を示し、Ra6は炭素数1〜10の2価の炭化水素基を示し、nは0〜10の整数を示す。Ra5としては、直鎖状又は分枝鎖状のアルキレン基、例えばメチレン基、エチレン基、プロピレン基、テトラメチレン基、エチルエチレン基、ペンタメチレン基、ヘキサメチレン基が好ましい。R13としては、例えばメチレン基、エチレン基、プロピレン基、テトラメチレン基、エチルエチレン基、ペンタメチレン基、ヘキサメチレン基、フェニレン基、シクロヘキシレン基、−CH2−Ph−CH2−(Phはフェニレン基を示す)が好ましい。 In the above formula, R a4 represents a hydrogen atom or a methyl group, R a5 represents a divalent saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, and R a6 represents a divalent hydrocarbon having 1 to 10 carbon atoms. Represents a group, and n represents an integer of 0 to 10. R a5 is preferably a linear or branched alkylene group such as a methylene group, an ethylene group, a propylene group, a tetramethylene group, an ethylethylene group, a pentamethylene group, or a hexamethylene group. Examples of R 13 include a methylene group, an ethylene group, a propylene group, a tetramethylene group, an ethylethylene group, a pentamethylene group, a hexamethylene group, a phenylene group, a cyclohexylene group, —CH 2 —Ph—CH 2 — (Ph is A phenylene group) is preferred.
(A)アルカリ可溶性樹脂は、上記(a1)単位、(a2)単位、及び(a3)単位の他の単位を含んでいてもよい。上記の単位の他の単位を与える化合物としては、(メタ)アクリル酸エステル類、(メタ)アクリルアミド類、アリル化合物、ビニルエーテル類、ビニルエステル類、スチレン類、脂環式基を有さないエポキシ基含有不飽和化合物等が挙げられる。これらの化合物は、単独又は2種以上組み合わせて用いることができる。 (A) The alkali-soluble resin may contain other units of the above (a1) unit, (a2) unit, and (a3) unit. Examples of compounds that give other units are the (meth) acrylic acid esters, (meth) acrylamides, allyl compounds, vinyl ethers, vinyl esters, styrenes, and epoxy groups having no alicyclic group. Examples thereof include unsaturated compounds. These compounds can be used alone or in combination of two or more.
(メタ)アクリル酸エステル類としては、メチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、アミル(メタ)アクリレート、t−オクチル(メタ)アクリレート等の直鎖状又は分岐鎖状のアルキル(メタ)アクリレート;クロロエチル(メタ)アクリレート、2,2−ジメチルヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、トリメチロールプロパンモノ(メタ)アクリレート、ベンジル(メタ)アクリレート、フルフリル(メタ)アクリレート;等が挙げられる。 As (meth) acrylic acid esters, linear or branched chain such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, amyl (meth) acrylate, t-octyl (meth) acrylate, etc. Alkyl (meth) acrylates; chloroethyl (meth) acrylate, 2,2-dimethylhydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, trimethylolpropane mono (meth) acrylate, benzyl (meth) acrylate, furfuryl (Meth) acrylate; etc. are mentioned.
(メタ)アクリルアミド類としては、(メタ)アクリルアミド、N−アルキル(メタ)アクリルアミド、N−アリール(メタ)アクリルアミド、N,N−ジアルキル(メタ)アクリルアミド、N,N−アリール(メタ)アクリルアミド、N−メチル−N−フェニル(メタ)アクリルアミド、N−ヒドロキシエチル−N−メチル(メタ)アクリルアミド等が挙げられる。 (Meth) acrylamides include (meth) acrylamide, N-alkyl (meth) acrylamide, N-aryl (meth) acrylamide, N, N-dialkyl (meth) acrylamide, N, N-aryl (meth) acrylamide, N -Methyl-N-phenyl (meth) acrylamide, N-hydroxyethyl-N-methyl (meth) acrylamide and the like.
アリル化合物としては、酢酸アリル、カプロン酸アリル、カプリル酸アリル、ラウリン酸アリル、パルミチン酸アリル、ステアリン酸アリル、安息香酸アリル、アセト酢酸アリル、乳酸アリル等のアリルエステル類;アリルオキシエタノール;等が挙げられる。 Examples of the allyl compound include allyl acetate, allyl caproate, allyl caprylate, allyl laurate, allyl palmitate, allyl stearate, allyl benzoate, allyl acetoacetate, allyl lactate, etc .; allyloxyethanol; Can be mentioned.
ビニルエーテル類としては、ヘキシルビニルエーテル、オクチルビニルエーテル、デシルビニルエーテル、エチルヘキシルビニルエーテル、メトキシエチルビニルエーテル、エトキシエチルビニルエーテル、クロルエチルビニルエーテル、1−メチル−2,2−ジメチルプロピルビニルエーテル、2−エチルブチルビニルエーテル、ヒドロキシエチルビニルエーテル、ジエチレングリコールビニルエーテル、ジメチルアミノエチルビニルエーテル、ジエチルアミノエチルビニルエーテル、ブチルアミノエチルビニルエーテル、ベンジルビニルエーテル、テトラヒドロフルフリルビニルエーテル等のアルキルビニルエーテル;ビニルフェニルエーテル、ビニルトリルエーテル、ビニルクロルフェニルエーテル、ビニル−2,4−ジクロルフェニルエーテル、ビニルナフチルエーテル、ビニルアントラニルエーテル等のビニルアリールエーテル;等が挙げられる。 As vinyl ethers, hexyl vinyl ether, octyl vinyl ether, decyl vinyl ether, ethyl hexyl vinyl ether, methoxyethyl vinyl ether, ethoxyethyl vinyl ether, chloroethyl vinyl ether, 1-methyl-2,2-dimethylpropyl vinyl ether, 2-ethylbutyl vinyl ether, hydroxyethyl vinyl ether , Alkyl vinyl ethers such as diethylene glycol vinyl ether, dimethylaminoethyl vinyl ether, diethylaminoethyl vinyl ether, butylaminoethyl vinyl ether, benzyl vinyl ether, tetrahydrofurfuryl vinyl ether; vinyl phenyl ether, vinyl tolyl ether, vinyl chlorophenyl ether, vinyl-2,4-dichloropheny And the like; ethers, vinyl naphthyl ether, vinyl aryl ethers such as vinyl anthranyl ether.
ビニルエステル類としては、ビニルブチレート、ビニルイソブチレート、ビニルトリメチルアセテート、ビニルジエチルアセテート、ビニルバレート、ビニルカプロエート、ビニルクロルアセテート、ビニルジクロルアセテート、ビニルメトキシアセテート、ビニルブトキシアセテート、ビニルフエニルアセテート、ビニルアセトアセテート、ビニルラクテート、ビニル−β−フェニルブチレート、安息香酸ビニル、サリチル酸ビニル、クロル安息香酸ビニル、テトラクロル安息香酸ビニル、ナフトエ酸ビニル等が挙げられる。 Vinyl esters include vinyl butyrate, vinyl isobutyrate, vinyl trimethyl acetate, vinyl diethyl acetate, vinyl valate, vinyl caproate, vinyl chloroacetate, vinyl dichloroacetate, vinyl methoxyacetate, vinyl butoxyacetate, vinyl vinyl. Examples include enyl acetate, vinyl acetoacetate, vinyl lactate, vinyl-β-phenylbutyrate, vinyl benzoate, vinyl salicylate, vinyl chlorobenzoate, vinyl tetrachlorobenzoate, vinyl naphthoate and the like.
スチレン類としては、スチレン;メチルスチレン、ジメチルスチレン、トリメチルスチレン、エチルスチレン、ジエチルスチレン、イソプロピルスチレン、ブチルスチレン、ヘキシルスチレン、シクロヘキシルスチレン、デシルスチレン、ベンジルスチレン、クロルメチルスチレン、トリフルオロメチルスチレン、エトキシメチルスチレン、アセトキシメチルスチレン等のアルキルスチレン;メトキシスチレン、4−メトキシ−3−メチルスチレン、ジメトキシスチレン等のアルコキシスチレン;クロロスチレン、ジクロロスチレン、トリクロロスチレン、テトラクロロスチレン、ペンタクロロスチレン、ブロモスチレン、ジブロモスチレン、ヨードスチレン、フルオロスチレン、トリフルオロスチレン、2−ブロモ−4−トリフルオロメチルスチレン、4−フルオロ−3−トリフルオロメチルスチレン等のハロスチレン;等が挙げられる。 Styrenes include: styrene; methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, isopropyl styrene, butyl styrene, hexyl styrene, cyclohexyl styrene, decyl styrene, benzyl styrene, chloromethyl styrene, trifluoromethyl styrene, ethoxy Alkyl styrene such as methyl styrene and acetoxymethyl styrene; alkoxy styrene such as methoxy styrene, 4-methoxy-3-methyl styrene and dimethoxy styrene; chlorostyrene, dichlorostyrene, trichlorostyrene, tetrachlorostyrene, pentachlorostyrene, bromostyrene, Dibromostyrene, iodostyrene, fluorostyrene, trifluorostyrene, 2-bromo-4-trifluoromethyl Styrene, halostyrenes such as 4-fluoro-3-trifluoromethyl styrene; and the like.
脂環式基を有さないエポキシ基含有不飽和化合物としては、グリシジル(メタ)アクリレート、2−メチルグリシジル(メタ)アクリレート、3,4−エポキシブチル(メタ)アクリレート、6,7−エポキシヘプチル(メタ)アクリレート等の(メタ)アクリル酸エポキシアルキルエステル類;α−エチルアクリル酸グリシジル、α−n−プロピルアクリル酸グリシジル、α−n−ブチルアクリル酸グリシジル、α−エチルアクリル酸6,7−エポキシヘプチル等のα−アルキルアクリル酸エポキシアルキルエステル類;等が挙げられる。これらの中では、グリシジル(メタ)アクリレート、2−メチルグリシジル(メタ)アクリレート、及び6,7−エポキシヘプチル(メタ)アクリレートが好ましい。 Examples of the epoxy group-containing unsaturated compound having no alicyclic group include glycidyl (meth) acrylate, 2-methylglycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, 6,7-epoxyheptyl ( (Meth) acrylate and other (meth) acrylic acid epoxy alkyl esters; α-ethyl acrylate glycidyl, α-n-propyl acrylate glycidyl, α-n-butyl acrylate glycidyl, α-ethyl acrylate 6,7-epoxy Α-alkyl acrylic acid epoxy alkyl esters such as heptyl; and the like. Among these, glycidyl (meth) acrylate, 2-methylglycidyl (meth) acrylate, and 6,7-epoxyheptyl (meth) acrylate are preferable.
(A)アルカリ可溶性樹脂である共重合体に占める、上記(a1)単位の割合と、上記(a2)単位の割合と、上記(a3)単位の割合とは、本発明の目的を阻害しない範囲で特に限定されない。(A)アルカリ可溶性樹脂である共重合体に占める上記(a1)単位の割合は、5〜25質量%が好ましく、8〜16質量%がより好ましい。(A)アルカリ可溶性樹脂である共重合体に占める上記(a2)単位の割合は、10〜50質量%が好ましく、11〜30質量%がより好ましい。(A)アルカリ可溶性樹脂である共重合体に占める上記(a3)単位の割合は、10〜70質量%が好ましく、15〜50質量%がより好ましい。 (A) The proportion of the (a1) unit, the proportion of the (a2) unit, and the proportion of the (a3) unit in the copolymer that is an alkali-soluble resin do not impair the purpose of the present invention. There is no particular limitation. (A) 5-25 mass% is preferable, and, as for the ratio of the said (a1) unit which occupies for the copolymer which is alkali-soluble resin, 8-16 mass% is more preferable. (A) 10-50 mass% is preferable and, as for the ratio of the said (a2) unit which occupies for the copolymer which is alkali-soluble resin, 11-30 mass% is more preferable. 10-70 mass% is preferable and, as for the ratio of the said (a3) unit occupied to the copolymer which is (A) alkali-soluble resin, 15-50 mass% is more preferable.
(A)アルカリ可溶性樹脂の質量平均分子量(Mw:ゲルパーミエーションクロマトグラフィ(GPC)のスチレン換算による測定値。本明細書において同じ。)は、2000〜200000が好ましく、2000〜18000がより好ましく、3000〜15000が特に好ましい。上記の範囲内の質量平均分子量の(A)アルカリ可溶性樹脂を用いることにより、感放射線性樹脂組成物の露光後の現像性を特に優れたものとしやすい。 (A) The mass average molecular weight of the alkali-soluble resin (Mw: measured value in terms of styrene by gel permeation chromatography (GPC). The same applies in this specification) is preferably 2000 to 200000, more preferably 2000 to 18000, and 3000. ˜15000 is particularly preferred. By using the (A) alkali-soluble resin having a mass average molecular weight within the above range, the developability after exposure of the radiation-sensitive resin composition is likely to be particularly excellent.
(A)アルカリ可用紙樹脂は公知のラジカル重合法により製造することができる。つまり、以上説明した単位を与える単量体と、公知のラジカル重合開始剤とを重合溶媒に溶解した後、加熱撹拌することにより製造することができる。 (A) The alkaline paper resin can be produced by a known radical polymerization method. That is, it can be produced by dissolving the monomer giving the above-described unit and a known radical polymerization initiator in a polymerization solvent and then stirring with heating.
<(B)光重合性化合物>
感放射線性樹脂組成物に含有される(B)光重合性化合物(以下、(B)成分とも記す。)としては、エチレン性不飽和基を有する化合物を好ましく用いることができる。このエチレン性不飽和基を有する化合物には、単官能化合物と多官能化合物とがある。
<(B) Photopolymerizable compound>
As the (B) photopolymerizable compound (hereinafter also referred to as component (B)) contained in the radiation-sensitive resin composition, a compound having an ethylenically unsaturated group can be preferably used. The compound having an ethylenically unsaturated group includes a monofunctional compound and a polyfunctional compound.
単官能化合物としては、(メタ)アクリルアミド、メチロール(メタ)アクリルアミド、メトキシメチル(メタ)アクリルアミド、エトキシメチル(メタ)アクリルアミド、プロポキシメチル(メタ)アクリルアミド、ブトキシメトキシメチル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N−ヒドロキシメチル(メタ)アクリルアミド、(メタ)アクリル酸、フマル酸、マレイン酸、無水マレイン酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、クロトン酸、2−アクリルアミド−2−メチルプロパンスルホン酸、tert−ブチルアクリルアミドスルホン酸、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、2−フェノキシ−2−ヒドロキシプロピル(メタ)アクリレート、2−(メタ)アクリロイルオキシ−2−ヒドロキシプロピルフタレート、グリセリンモノ(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、ジメチルアミノ(メタ)アクリレート、グリシジル(メタ)アクリレート、2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3−テトラフルオロプロピル(メタ)アクリレート、フタル酸誘導体のハーフ(メタ)アクリレート等が挙げられる。これらの単官能モノマーは、単独又は2種以上組み合わせて用いることができる。 Monofunctional compounds include (meth) acrylamide, methylol (meth) acrylamide, methoxymethyl (meth) acrylamide, ethoxymethyl (meth) acrylamide, propoxymethyl (meth) acrylamide, butoxymethoxymethyl (meth) acrylamide, N-methylol ( (Meth) acrylamide, N-hydroxymethyl (meth) acrylamide, (meth) acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, crotonic acid, 2-acrylamide- 2-methylpropanesulfonic acid, tert-butylacrylamidesulfonic acid, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate , Cyclohexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) acrylate, 2- ( (Meth) acryloyloxy-2-hydroxypropyl phthalate, glycerin mono (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, dimethylamino (meth) acrylate, glycidyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) ) Acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, and half (meth) acrylate of a phthalic acid derivative. These monofunctional monomers can be used alone or in combination of two or more.
一方、多官能モノマーとしては、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、ブチレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,6−ヘキサングリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、グリセリンジ(メタ)アクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、ペンタエリスリトールジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、2,2−ビス(4−(メタ)アクリロキシジエトキシフェニル)プロパン、2,2−ビス(4−(メタ)アクリロキシポリエトキシフェニル)プロパン、2−ヒドロキシ−3−(メタ)アクリロイルオキシプロピル(メタ)アクリレート、エチレングリコールジグリシジルエーテルジ(メタ)アクリレート、ジエチレングリコールジグリシジルエーテルジ(メタ)アクリレート、フタル酸ジグリシジルエステルジ(メタ)アクリレート、グリセリントリアクリレート、グリセリンポリグリシジルエーテルポリ(メタ)アクリレート、ウレタン(メタ)アクリレート(すなわち、トリレンジイソシアネート)、トリメチルヘキサメチレンジイソシアネートとヘキサメチレンジイソシアネート等と2−ビドロキシエチル(メタ)アクリレートとの反応物、メチレンビス(メタ)アクリルアミド、(メタ)アクリルアミドメチレンエーテル、多価アルコールとN−メチロール(メタ)アクリルアミドとの縮合物、トリアクリルホルマール、2,4,6−トリオキソヘキサヒドロ−1,3,5−トリアジン−1,3,5−トリスエタノールトリアクリレート、及び2,4,6−トリオキソヘキサヒドロ−1,3,5−トリアジン−1,3,5−トリスエタノールジアクリレート等が挙げられる。これらの多官能モノマーは、単独又は2種以上組み合わせて用いることができる。 On the other hand, as the polyfunctional monomer, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol Di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexane glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerin di (meth) acrylate, pentaerythritol triacrylate, pentaerythritol Tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di (meta Acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 2,2-bis (4- (meth) acryloxydi Ethoxyphenyl) propane, 2,2-bis (4- (meth) acryloxypolyethoxyphenyl) propane, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, ethylene glycol diglycidyl ether di (meth) Acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, diglycidyl phthalate ester di (meth) acrylate, glycerin triacrylate, glycerin polyglycidyl ether poly (Meth) acrylate, urethane (meth) acrylate (that is, tolylene diisocyanate), reaction product of trimethylhexamethylene diisocyanate and hexamethylene diisocyanate and 2-bidoxyethyl (meth) acrylate, methylenebis (meth) acrylamide, (meth) acrylamide methylene Ether, condensate of polyhydric alcohol and N-methylol (meth) acrylamide, triacryl formal, 2,4,6-trioxohexahydro-1,3,5-triazine-1,3,5-trisethanoltri Examples thereof include acrylates and 2,4,6-trioxohexahydro-1,3,5-triazine-1,3,5-trisethanol diacrylate. These polyfunctional monomers can be used alone or in combination of two or more.
これらのエチレン性不飽和基を有する化合物の中でも、強度と、基板への密着性とに優れる硬化物を与える感放射線性樹脂組成物が得られる点から、3官能以上の多官能モノマーが好ましい。 Among these compounds having an ethylenically unsaturated group, a polyfunctional monomer having three or more functional groups is preferable from the viewpoint of obtaining a radiation-sensitive resin composition that gives a cured product excellent in strength and adhesion to a substrate.
(B)成分の含有量は、感放射線性樹脂組成物の固形分に対して5〜60質量%が好ましく、10〜50質量%がより好ましい。感放射線性樹脂組成物中の(B)成分の含有量を上記の範囲とすることにより、感放射線性樹脂組成物の感度、現像性、及び解像性のバランスをとりやすい傾向がある。 (B) 5-60 mass% is preferable with respect to solid content of a radiation sensitive resin composition, and, as for content of a component, 10-50 mass% is more preferable. By making content of (B) component in a radiation sensitive resin composition into said range, there exists a tendency which is easy to balance the sensitivity of a radiation sensitive resin composition, developability, and resolution.
<(C)光重合性化合物>
感放射線性樹脂組成物は、(C)光重合開始剤(以下、(C)成分とも記す。)として、下記構造のオキシムエステル化合物を含有する。光重合開始剤として、下記式(1)で表される構造のオキシムエステル化合物を用いることにより、透明性に優れる硬化膜を形成可能な感放射線性樹脂組成物を得ることができる。
<(C) Photopolymerizable compound>
The radiation-sensitive resin composition contains an oxime ester compound having the following structure as a photopolymerization initiator (C) (hereinafter also referred to as component (C)). By using an oxime ester compound having a structure represented by the following formula (1) as a photopolymerization initiator, a radiation-sensitive resin composition capable of forming a cured film having excellent transparency can be obtained.
上記式(1)中、R1が1価の有機基である場合、R1は、本発明の目的を阻害しない範囲で特に限定されず、種々の有機基から適宜選択される。R1が有機基である場合の好適な例としては、アルキル基、アルコキシ基、シクロアルキル基、シクロアルコキシ基、飽和脂肪族アシル基、アルコキシカルボニル基、飽和脂肪族アシルオキシ基、置換基を有してもよいフェニル基、置換基を有してもよいフェノキシ基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよいベンゾイルオキシ基、置換基を有してもよいフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトキシ基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよいナフトイルオキシ基、置換基を有してもよいナフチルアルキル基、置換基を有してもよいヘテロシクリル基、1、又は2の有機基で置換されたアミノ基、モルホリン−1−イル基、及びピペラジン−1−イル基等が挙げられる。mが2〜4の整数である場合、R1は同一であっても異なっていてもよい。また、置換基の炭素数には、置換基がさらに有する置換基の炭素数は含まない。 In the above formula (1), when R 1 is a monovalent organic group, R 1 is not particularly limited as long as the object of the present invention is not impaired, and is appropriately selected from various organic groups. Preferred examples when R1 is an organic group include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, and a substituent. A phenyl group which may have a substituent, a phenoxy group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a benzoyloxy group which may have a substituent A phenylalkyl group which may have a substituent, a naphthyl group which may have a substituent, a naphthoxy group which may have a substituent, a naphthoyl group which may have a substituent, and a substituent. A naphthoxycarbonyl group which may have a substituent, a naphthyloxy group which may have a substituent, a naphthylalkyl group which may have a substituent, a heterocyclyl group which may have a substituent, Is substituted with two organic groups are amino groups, morpholin-1-yl group, and piperazine-1-yl group. When m is an integer of 2 to 4, R 1 may be the same or different. Moreover, the carbon number of the substituent does not include the carbon number of the substituent that the substituent further has.
R1がアルキル基である場合、その炭素数は1〜20が好ましく、1〜6がより好ましい。また、R1がアルキル基である場合、直鎖であっても、分岐鎖であってもよい。R1がアルキル基である場合の具体例としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、sec−ペンチル基、tert−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、イソオクチル基、sec−オクチル基、tert−オクチル基、n−ノニル基、イソノニル基、n−デシル基、及びイソデシル基等が挙げられる。また、R1がアルキル基である場合、アルキル基は炭素鎖中にエーテル結合(−O−)を含んでいてもよい。炭素鎖中にエーテル結合を有するアルキル基の例としては、メトキシエチル基、エトキシエチル基、メトキシエトキシエチル基、エトキシエトキシエチル基、プロピルオキシエトキシエチル基、及びメトキシプロピル基等が挙げられる。 When R 1 is an alkyl group, the number of carbon atoms is preferably from 1 to 20, 1 to 6 is more preferable. Further, when R 1 is an alkyl group, it may be linear or branched. Specific examples in the case where R 1 is an alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and an n-pentyl group. , Isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, An n-decyl group, an isodecyl group, etc. are mentioned. When R 1 is an alkyl group, the alkyl group may include an ether bond (—O—) in the carbon chain. Examples of the alkyl group having an ether bond in the carbon chain include a methoxyethyl group, an ethoxyethyl group, a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.
R1がアルコキシ基である場合、その炭素数は1〜20が好ましく、1〜6がより好ましい。また、R1がアルコキシ基である場合、直鎖であっても、分岐鎖であってもよい。R1がアルコキシ基である場合の具体例としては、メトキシ基、エトキシ基、n−プロピルオキシ基、イソプロピルオキシ基、n−ブチルオキシ基、イソブチルオキシ基、sec−ブチルオキシ基、tert−ブチルオキシ基、n−ペンチルオキシ基、イソペンチルオキシ基、sec−ペンチルオキシ基、tert−ペンチルオキシ基、n−ヘキシルオキシ基、n−ヘプチルオキシ基、n−オクチルオキシ基、イソオクチルオキシ基、sec−オクチオキシル基、tert−オクチルオキシ基、n−ノニルオキシ基、イソノニルオキシ基、n−デシルオキシ基、及びイソデシルオキシ基等が挙げられる。また、R1がアルコキシ基である場合、アルコキシ基は炭素鎖中にエーテル結合(−O−)を含んでいてもよい。炭素鎖中にエーテル結合を有するアルコキシ基の例としては、メトキシエトキシ基、エトキシエトキシ基、メトキシエトキシエトキシ基、エトキシエトキシエトキシ基、プロピルオキシエトキシエトキシ基、及びメトキシプロピルオキシ基等が挙げられる。 When R 1 is an alkoxy group, the carbon number is preferably 1-20, and more preferably 1-6. Further, when R 1 is an alkoxy group, it may be linear or branched. Specific examples when R 1 is an alkoxy group include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n -Pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec-octoxyl group, Examples thereof include a tert-octyloxy group, an n-nonyloxy group, an isononyloxy group, an n-decyloxy group, and an isodecyloxy group. When R 1 is an alkoxy group, the alkoxy group may contain an ether bond (—O—) in the carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include a methoxyethoxy group, an ethoxyethoxy group, a methoxyethoxyethoxy group, an ethoxyethoxyethoxy group, a propyloxyethoxyethoxy group, and a methoxypropyloxy group.
R1がシクロアルキル基、又はシクロアルコキシ基である場合、その炭素数は3〜10が好ましく、3〜6がより好ましい。R1がシクロアルキル基である場合の具体例としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、及びシクロオクチル基等が挙げられる。R1がシクロアルコキシ基である場合の具体例としては、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、及びシクロオクチルオキシ基等が挙げられる。 When R 1 is a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms is preferably 3 to 10, and more preferably 3 to 6. Specific examples of when R 1 is a cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Specific examples when R 1 is a cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.
R1が飽和脂肪族アシル基、又は飽和脂肪族アシルオキシ基である場合、その炭素数は2〜20が好ましく、2〜7がより好ましい。R1が飽和脂肪族アシル基である場合の具体例としては、アセチル基、プロパノイル基、n−ブタノイル基、2−メチルプロパノイル基、n−ペンタノイル基、2,2−ジメチルプロパノイル基、n−ヘキサノイル基、n−ヘプタノイル基、n−オクタノイル基、n−ノナノイル基、n−デカノイル基、n−ウンデカノイル基、n−ドデカノイル基、n−トリデカノイル基、n−テトラデカノイル基、n−ペンタデカノイル基、及びn−ヘキサデカノイル基等が挙げられる。R1が飽和脂肪族アシルオキシ基である場合の具体例としては、アセチルオキシ基、プロパノイルオキシ基、n−ブタノイルオキシ基、2−メチルプロパノイルオキシ基、n−ペンタノイルオキシ基、2,2−ジメチルプロパノイルオキシ基、n−ヘキサノイルオキシ基、n−ヘプタノイルオキシ基、n−オクタノイルオキシ基、n−ノナノイルオキシ基、n−デカノイルオキシ基、n−ウンデカノイルオキシ基、n−ドデカノイルオキシ基、n−トリデカノイルオキシ基、n−テトラデカノイルオキシ基、n−ペンタデカノイルオキシ基、及びn−ヘキサデカノイルオキシ基等が挙げられる。 When R 1 is a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, the carbon number thereof is preferably 2 to 20, and more preferably 2 to 7. Specific examples when R 1 is a saturated aliphatic acyl group include acetyl group, propanoyl group, n-butanoyl group, 2-methylpropanoyl group, n-pentanoyl group, 2,2-dimethylpropanoyl group, n -Hexanoyl group, n-heptanoyl group, n-octanoyl group, n-nonanoyl group, n-decanoyl group, n-undecanoyl group, n-dodecanoyl group, n-tridecanoyl group, n-tetradecanoyl group, n-pentadecanyl group Examples include a noyl group and an n-hexadecanoyl group. Specific examples when R 1 is a saturated aliphatic acyloxy group include acetyloxy group, propanoyloxy group, n-butanoyloxy group, 2-methylpropanoyloxy group, n-pentanoyloxy group, 2, 2-dimethylpropanoyloxy group, n-hexanoyloxy group, n-heptanoyloxy group, n-octanoyloxy group, n-nonanoyloxy group, n-decanoyloxy group, n-undecanoyloxy group, n -Dodecanoyloxy group, n-tridecanoyloxy group, n-tetradecanoyloxy group, n-pentadecanoyloxy group, n-hexadecanoyloxy group and the like.
R1がアルコキシカルボニル基である場合、その炭素数は2〜20が好ましく、2〜7がより好ましい。R1がアルコキシカルボニル基である場合の具体例としては、メトキシカルボニル基、エトキシカルボニル基、n−プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、n−ブチルオキシカルボニル基、イソブチルオキシカルボニル基、sec−ブチルオキシカルボニル基、tert−ブチルオキシカルボニル基、n−ペンチルオキシカルボニル基、イソペンチルオキシカルボニル基、sec−ペンチルオキシカルボニル基、tert−ペンチルオキシカルボニル基、n−ヘキシルオキシカルボニル基、n−ヘプチルオキシカルボニル基、n−オクチルオキシカルボニル基、イソオクチルオキシカルボニル基、sec−オクチオキシルカルボニル基、tert−オクチルオキシカルボニル基、n−ノニルオキシカルボニル基、イソノニルオキシカルボニル基、n−デシルオキシカルボニル基、及びイソデシルオキシカルボニル基等が挙げられる。 When R 1 is an alkoxycarbonyl group, the carbon number thereof is preferably 2 to 20, and more preferably 2 to 7. Specific examples in the case where R 1 is an alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyl. Oxycarbonyl group, tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, sec-pentyloxycarbonyl group, tert-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl Group, n-octyloxycarbonyl group, isooctyloxycarbonyl group, sec-octyloxycarbonyl group, tert-octyloxycarbonyl group, n-nonyloxycarbonyl group, i Examples include a sononyloxycarbonyl group, an n-decyloxycarbonyl group, and an isodecyloxycarbonyl group.
R1がフェニルアルキル基である場合、その炭素数は7〜20が好ましく、7〜10がより好ましい。またR1がナフチルアルキル基である場合、その炭素数は11〜20が好ましく、11〜14がより好ましい。R1がフェニルアルキル基である場合の具体例としては、ベンジル基、2−フェニルエチル基、3−フェニルプロピル基、及び4−フェニルブチル基が挙げられる。R1がナフチルアルキル基である場合の具体例としては、α−ナフチルメチル基、β−ナフチルメチル基、2−(α−ナフチル)エチル基、及び2−(β−ナフチル)エチル基が挙げられる。R1が、フェニルアルキル基、又はナフチルアルキル基である場合、R1は、フェニル基、又はナフチル基上にさらに置換基を有していてもよい。 When R 1 is a phenylalkyl group, the carbon number thereof is preferably 7-20, and more preferably 7-10. Also when R 1 is a naphthyl group, the number of carbon atoms is preferably from 11 to 20, 11 to 14 is more preferable. Specific examples when R 1 is a phenylalkyl group include a benzyl group, a 2-phenylethyl group, a 3-phenylpropyl group, and a 4-phenylbutyl group. Specific examples in the case where R 1 is a naphthylalkyl group include an α-naphthylmethyl group, a β-naphthylmethyl group, a 2- (α-naphthyl) ethyl group, and a 2- (β-naphthyl) ethyl group. . When R 1 is a phenylalkyl group or a naphthylalkyl group, R 1 may further have a substituent on the phenyl group or naphthyl group.
R1がヘテロシクリル基である場合、ヘテロシクリル基は、1以上のN、S、Oを含む5員又は6員の単環であるか、かかる単環同士、又はかかる単環とベンゼン環とが縮合したヘテロシクリル基である。ヘテロシクリル基が縮合環である場合は、環数3までのものとする。かかるヘテロシクリル基を構成する複素環としては、フラン、チオフェン、ピロール、オキサゾール、イソオキサゾール、チアゾール、チアジアゾール、イソチアゾール、イミダゾール、ピラゾール、トリアゾール、ピリジン、ピラジン、ピリミジン、ピリダジン、ベンゾフラン、ベンゾチオフェン、インドール、イソインドール、インドリジン、ベンゾイミダゾール、ベンゾトリアゾール、ベンゾオキサゾール、ベンゾチアゾール、カルバゾール、プリン、キノリン、イソキノリン、キナゾリン、フタラジン、シンノリン、及びキノキサリン等が挙げられる。R1がヘテロシクリル基である場合、ヘテロシクリル基はさらに置換基を有していてもよい。 When R 1 is a heterocyclyl group, the heterocyclyl group is a 5-membered or 6-membered monocycle containing one or more N, S, and O, such monocycles, or such monocycles and benzene rings are condensed. Heterocyclyl group. When the heterocyclyl group is a condensed ring, the ring number is up to 3. Examples of the heterocyclic ring constituting the heterocyclyl group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, Examples include isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, and quinoxaline. When R 1 is a heterocyclyl group, the heterocyclyl group may further have a substituent.
R1が1又は2の有機基で置換されたアミノ基である場合、有機基の好適な例は、炭素数1〜20のアルキル基、炭素数3〜10のシクロアルキル基、炭素数2〜20の飽和脂肪族アシル基、置換基を有してもよいフェニル基、置換基を有してもよいベンゾイル基、置換基を有してもよい炭素数7〜20のフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトイル基、置換基を有してもよい炭素数11〜20のナフチルアルキル基、及びヘテロシクリル基等が挙げられる。これらの好適な有機基の具体例は、R1と同様である。1、又は2の有機基で置換されたアミノ基の具体例としては、メチルアミノ基、エチルアミノ基、ジエチルアミノ基、n−プロピルアミノ基、ジ−n−プロピルアミノ基、イソプロピルアミノ基、n−ブチルアミノ基、ジ−n−ブチルアミノ基、n−ペンチルアミノ基、n−ヘキシルアミノ基、n−ヘプチルアミノ基、n−オクチルアミノ基、n−ノニルアミノ基、n−デシルアミノ基、フェニルアミノ基、ナフチルアミノ基、アセチルアミノ基、プロパノイルアミノ基、n−ブタノイルアミノ基、n−ペンタノイルアミノ基、n−ヘキサノイルアミノ基、n−ヘプタノイルアミノ基、n−オクタノイルアミノ基、n−デカノイルアミノ基、ベンゾイルアミノ基、α−ナフトイルアミノ基、及びβ−ナフトイルアミノ基等が挙げられる。 When R 1 is an amino group substituted with an organic group having 1 or 2, suitable examples of the organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and 2 to 2 carbon atoms. 20 saturated aliphatic acyl groups, optionally substituted phenyl groups, optionally substituted benzoyl groups, optionally substituted C 7-20 phenylalkyl groups, substituents A naphthyl group that may have a substituent, a naphthoyl group that may have a substituent, a naphthylalkyl group having 11 to 20 carbon atoms that may have a substituent, a heterocyclyl group, and the like. Specific examples of these suitable organic groups are the same as those for R 1 . Specific examples of the amino group substituted with 1 or 2 organic groups include methylamino group, ethylamino group, diethylamino group, n-propylamino group, di-n-propylamino group, isopropylamino group, n- Butylamino group, di-n-butylamino group, n-pentylamino group, n-hexylamino group, n-heptylamino group, n-octylamino group, n-nonylamino group, n-decylamino group, phenylamino group, Naphthylamino group, acetylamino group, propanoylamino group, n-butanoylamino group, n-pentanoylamino group, n-hexanoylamino group, n-heptanoylamino group, n-octanoylamino group, n- Examples include a decanoylamino group, a benzoylamino group, an α-naphthoylamino group, and a β-naphthoylamino group.
R1に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合の置換基としては、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数2〜7の飽和脂肪族アシル基、炭素数2〜7のアルコキシカルボニル基、炭素数2〜7の飽和脂肪族アシルオキシ基、炭素数1〜6のアルキル基を有するモノアルキルアミノ基、炭素数1〜6のアルキル基を有するジアルキルアミノ基、モルホリン−1−イル基、ピペラジン−1−イル基、ハロゲン、ニトロ基、及びシアノ基等が挙げられる。R1に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合、その置換基の数は、本発明の目的を阻害しない範囲で限定されないが、1〜4が好ましい。R1に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基が、複数の置換基を有する場合、複数の置換基は、同一であっても異なっていてもよい。 Examples of the substituent when the phenyl group, naphthyl group, and heterocyclyl group included in R 1 further have a substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and 2 to 2 carbon atoms. A saturated aliphatic acyl group having 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms And a dialkylamino group having an alkyl group, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in R 1 further have a substituent, the number of the substituent is not limited as long as the object of the present invention is not impaired, but 1 to 4 is preferable. When the phenyl group, naphthyl group, and heterocyclyl group contained in R 1 have a plurality of substituents, the plurality of substituents may be the same or different.
R1の中では、化学的に安定であることや、立体的な障害が少なく、オキシムエステル化合物の合成が容易であることや、溶媒に対する溶解性が高いこと等から、ニトロ基、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、及び炭素数2〜7の飽和脂肪族アシル基からなる群より選択される基が好ましく、ニトロ基、又は炭素数1〜6のアルキルがより好ましく、ニトロ基、又はメチル基が特に好ましい。 Among R 1 , nitro group, carbon number 1 because of chemical stability, few steric hindrances, easy synthesis of oxime ester compounds, high solubility in solvents, etc. A group selected from the group consisting of an alkyl group having ˜6, an alkoxy group having 1 to 6 carbon atoms, and a saturated aliphatic acyl group having 2 to 7 carbon atoms is preferable, and a nitro group or an alkyl having 1 to 6 carbon atoms is More preferred is a nitro group or a methyl group.
R1がフェニル基に結合する位置は、R1が結合するフェニル基について、フェニル基とオキシムエステル化合物の主骨格との結合手の位置を1位とし、メチル基の位置を2位とする場合に、4位、又は5位が好ましく、5位がよりに好ましい。また、mは、0〜3の整数が好ましく、0〜2の整数がより好ましく、0、又は1が特に好ましい。 Positions R 1 is bonded to the phenyl group, the phenyl group R 1 is attached, the position of the bond to the main chain of the phenyl group and the oxime ester compound as a 1-position, if the 2-position of the position of the methyl group 4th or 5th is preferable, and 5th is more preferable. M is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1.
R2は、置換基を有してもよいフェニル基、又は置換基を有してもよいカルバゾリル基である。また、R2が置換基を有してもよいカルバゾリル基である場合、カルバゾリル基上の窒素原子は、炭素数1〜6のアルキル基で置換されていてもよい。 R 2 is a phenyl group which may have a substituent, or a carbazolyl group which may have a substituent. When R 2 is a carbazolyl group which may have a substituent, the nitrogen atom on the carbazolyl group may be substituted with an alkyl group having 1 to 6 carbon atoms.
R2において、フェニル基、又はカルバゾリル基が有する置換基は、本発明の目的を阻害しない範囲で特に限定されない。フェニル基、又はカルバゾリル基が、炭素原子上に有してもよい好適な置換基の例としては、炭素数1〜20のアルキル基、炭素数1〜20のアルコキシ基、炭素数3〜10のシクロアルキル基、炭素数3〜10のシクロアルコキシ基、炭素数2〜20の飽和脂肪族アシル基、炭素数2〜20のアルコキシカルボニル基、炭素数2〜20の飽和脂肪族アシルオキシ基、置換基を有してもよいフェニル基、置換基を有してもよいフェノキシ基、置換基を有してもよいフェニルチオ基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよいベンゾイルオキシ基、置換基を有してもよい炭素数7〜20のフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトキシ基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよいナフトイルオキシ基、置換基を有してもよい炭素数11〜20のナフチルアルキル基、置換基を有してもよいヘテロシクリル基、置換基を有してもよいヘテロシクリルカルボニル基、アミノ基、1、又は2の有機基で置換されたアミノ基、モルホリン−1−イル基、及びピペラジン−1−イル基、ハロゲン、ニトロ基、及びシアノ基等が挙げられる。 In R 2 , the substituent that the phenyl group or carbazolyl group has is not particularly limited as long as the object of the present invention is not impaired. Examples of suitable substituents that the phenyl group or carbazolyl group may have on the carbon atom include alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, and 3 to 10 carbon atoms. A cycloalkyl group, a C3-C10 cycloalkoxy group, a C2-C20 saturated aliphatic acyl group, a C2-C20 alkoxycarbonyl group, a C2-C20 saturated aliphatic acyloxy group, a substituent A phenyl group that may have a substituent, a phenoxy group that may have a substituent, a phenylthio group that may have a substituent, a benzoyl group that may have a substituent, and a substituent. Phenoxycarbonyl group, benzoyloxy group which may have a substituent, phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, naphthyl group which may have a substituent, and a substituent Naftoki Group, an optionally substituted naphthoyl group, an optionally substituted naphthoxycarbonyl group, an optionally substituted naphthoyloxy group, and an optionally substituted carbon number 11 -20 naphthylalkyl group, optionally substituted heterocyclyl group, optionally substituted heterocyclylcarbonyl group, amino group, amino group substituted with 1 or 2 organic groups, morpholine-1 -Yl group, piperazin-1-yl group, halogen, nitro group, cyano group and the like can be mentioned.
R2がカルバゾリル基である場合、カルバゾリル基が窒素原子上に有してもよい好適な置換基の例としては、炭素数1〜20のアルキル基、炭素数3〜10のシクロアルキル基、炭素数2〜20の飽和脂肪族アシル基、炭素数2〜20のアルコキシカルボニル基、置換基を有してもよいフェニル基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよい炭素数7〜20のフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよい炭素数11〜20のナフチルアルキル基、置換基を有してもよいヘテロシクリル基、及び置換基を有してもよいヘテロシクリルカルボニル基等が挙げられる。これらの置換基の中では、炭素数1〜20のアルキル基が好ましく、炭素数1〜6のアルキル基がより好ましく、エチル基が特に好ましい。 When R 2 is a carbazolyl group, examples of suitable substituents that the carbazolyl group may have on the nitrogen atom include alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, carbon A saturated aliphatic acyl group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a phenyl group which may have a substituent, a benzoyl group which may have a substituent, and a substituent. A good phenoxycarbonyl group, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoyl group which may have a substituent, and a substituent A naphthoxycarbonyl group which may have a substituent, a naphthylalkyl group having 11 to 20 carbon atoms which may have a substituent, a heterocyclyl group which may have a substituent, a heterocyclylcarbonyl group which may have a substituent, etc. Raised It is done. Among these substituents, an alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and an ethyl group is particularly preferable.
フェニル基、又はカルバゾリル基が有してもよい置換基の具体例について、アルキル基、アルコキシ基、シクロアルキル基、シクロアルコキシ基、飽和脂肪族アシル基、アルコキシカルボニル基、飽和脂肪族アシルオキシ基、置換基を有してもよいフェニルアルキル基、置換基を有してもよいナフチルアルキル基、置換基を有してもよいヘテロシクリル基、及び1、又は2の有機基で置換されたアミノ基に関しては、R1と同様である。 Specific examples of the substituent that the phenyl group or carbazolyl group may have include an alkyl group, an alkoxy group, a cycloalkyl group, a cycloalkoxy group, a saturated aliphatic acyl group, an alkoxycarbonyl group, a saturated aliphatic acyloxy group, and a substituent. With respect to an optionally substituted phenylalkyl group, an optionally substituted naphthylalkyl group, an optionally substituted heterocyclyl group, and an amino group substituted with one or two organic groups , R 1 .
R2において、フェニル基、又はカルバゾリル基が有する置換基に含まれるフェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合の置換基の例としては、炭素数1〜6のアルキル基;炭素数1〜6のアルコキシ基;炭素数2〜7の飽和脂肪族アシル基;炭素数2〜7のアルコキシカルボニル基;炭素数2〜7の飽和脂肪族アシルオキシ基;フェニル基;ナフチル基;ベンゾイル基;ナフトイル基;炭素数1〜6のアルキル基、モルホリン−1−イル基、ピペラジン−1−イル基、及びフェニル基からなる群より選択される基により置換されたベンゾイル基;炭素数1〜6のアルキル基を有するモノアルキルアミノ基;炭素数1〜6のアルキル基を有するジアルキルアミノ基;モルホリン−1−イル基;ピペラジン−1−イル基;ハロゲン;ニトロ基;シアノ基が挙げられる。フェニル基、又はカルバゾリル基が有する置換基に含まれるフェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合、その置換基の数は、本発明の目的を阻害しない範囲で限定されないが、1〜4が好ましい。フェニル基、ナフチル基、及びヘテロシクリル基が、複数の置換基を有する場合、複数の置換基は、同一であっても異なっていてもよい。 Examples of the substituent when the phenyl group, the naphthyl group, and the heterocyclyl group included in the substituent of the phenyl group or the carbazolyl group in R 2 further have a substituent include an alkyl group having 1 to 6 carbon atoms; An alkoxy group having 1 to 6 carbon atoms; a saturated aliphatic acyl group having 2 to 7 carbon atoms; an alkoxycarbonyl group having 2 to 7 carbon atoms; a saturated aliphatic acyloxy group having 2 to 7 carbon atoms; a phenyl group; a naphthyl group; A benzoyl group substituted with a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; Monoalkylamino group having 6 alkyl groups; dialkylamino group having 1 to 6 carbon atoms; morpholin-1-yl group; piperazine-1 -Yl group; halogen; nitro group; cyano group. When the phenyl group, the naphthyl group, and the heterocyclyl group included in the substituent of the phenyl group or carbazolyl group further have a substituent, the number of the substituent is not limited as long as the object of the present invention is not impaired. 1-4 are preferable. When the phenyl group, naphthyl group, and heterocyclyl group have a plurality of substituents, the plurality of substituents may be the same or different.
R2の中では、感放射線性樹脂組成物が感度に優れる点から、下記式(2)、又は(3)で表される基が好ましく、下記式(2)で表される基がより好ましく、下記式(2)で表される基であって、AがSである基が特に好ましい。 Among R 2 , a group represented by the following formula (2) or (3) is preferable, and a group represented by the following formula (2) is more preferable because the radiation-sensitive resin composition is excellent in sensitivity. A group represented by the following formula (2) in which A is S is particularly preferable.
式(2)におけるR4が有機基である場合、本発明の目的を阻害しない範囲で、種々の有機基から選択できる。式(2)においてR4が有機基である場合の好適な例としては、炭素数1〜6のアルキル基;炭素数1〜6のアルコキシ基;炭素数2〜7の飽和脂肪族アシル基;炭素数2〜7のアルコキシカルボニル基;炭素数2〜7の飽和脂肪族アシルオキシ基;フェニル基;ナフチル基;ベンゾイル基;ナフトイル基;炭素数1〜6のアルキル基、モルホリン−1−イル基、ピペラジン−1−イル基、及びフェニル基からなる群より選択される基により置換されたベンゾイル基;炭素数1〜6のアルキル基を有するモノアルキルアミノ基;炭素数1〜6のアルキル基を有するジアルキルアミノ基;モルホリン−1−イル基;ピペラジン−1−イル基;ハロゲン;ニトロ基;シアノ基が挙げられる。 When R 4 in the formula (2) is an organic group, it can be selected from various organic groups as long as the object of the present invention is not impaired. Preferable example of R 4 in the formula (2) is an organic group, an alkyl group having 1 to 6 carbon atoms; saturated aliphatic acyl group having 2 to 7 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; An alkoxycarbonyl group having 2 to 7 carbon atoms; a saturated aliphatic acyloxy group having 2 to 7 carbon atoms; a phenyl group; a naphthyl group; a benzoyl group; a naphthoyl group; an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, A benzoyl group substituted by a group selected from the group consisting of a piperazin-1-yl group and a phenyl group; a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms; an alkyl group having 1 to 6 carbon atoms A dialkylamino group; a morpholin-1-yl group; a piperazin-1-yl group; a halogen; a nitro group; and a cyano group.
R4の中では、ベンゾイル基;ナフトイル基;炭素数1〜6のアルキル基、モルホリン−1−イル基、ピペラジン−1−イル基、及びフェニル基からなる群より選択される基により置換されたベンゾイル基;ニトロ基が好ましく、ベンゾイル基;ナフトイル基;2−メチルフェニルカルボニル基;4−(ピペラジン−1−イル)フェニルカルボニル基;4−(フェニル)フェニルカルボニル基がより好ましい。 In R 4 , substituted by a group selected from the group consisting of benzoyl group; naphthoyl group; alkyl group having 1 to 6 carbon atoms, morpholin-1-yl group, piperazin-1-yl group, and phenyl group Benzoyl group; nitro group is preferred, benzoyl group; naphthoyl group; 2-methylphenylcarbonyl group; 4- (piperazin-1-yl) phenylcarbonyl group; 4- (phenyl) phenylcarbonyl group is more preferred.
また、式(2)において、nは、0〜3の整数が好ましく、0〜2の整数がより好ましく、0、又は1であるのが特に好ましい。nが1である場合、R4の結合する位置は、R4が結合するフェニル基が硫黄原子と結合する結合手に対して、パラ位であるのが好ましい。 In the formula (2), n is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1. when n is 1, the binding position of R 4 is, relative to the bond to the phenyl group R 4 is bonded is bonded to the sulfur atom is preferably in the para position.
式(3)におけるR5は、本発明の目的を阻害しない範囲で、種々の有機基から選択できる。R5の好適な例としては、炭素数1〜20のアルキル基、炭素数3〜10のシクロアルキル基、炭素数2〜20の飽和脂肪族アシル基、炭素数2〜20のアルコキシカルボニル基、置換基を有してもよいフェニル基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよい炭素数7〜20のフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよい炭素数11〜20のナフチルアルキル基、置換基を有してもよいヘテロシクリル基、及び置換基を有してもよいヘテロシクリルカルボニル基等が挙げられる。 R 5 in Formula (3) can be selected from various organic groups as long as the object of the present invention is not impaired. Preferable examples of R 5 include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a saturated aliphatic acyl group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, Phenyl group which may have a substituent, benzoyl group which may have a substituent, phenoxycarbonyl group which may have a substituent, phenylalkyl having 7 to 20 carbon atoms which may have a substituent Group, an optionally substituted naphthyl group, an optionally substituted naphthoyl group, an optionally substituted naphthoxycarbonyl group, and an optionally substituted carbon number 11 to 20 Naphthylalkyl group, a heterocyclyl group which may have a substituent, a heterocyclylcarbonyl group which may have a substituent, and the like.
R5の中では、炭素数1〜20のアルキル基が好ましく、炭素数1〜6のアルキル基がより好ましく、エチル基が特に好ましい。 Among R 5 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, an ethyl group is particularly preferred.
式(3)におけるR6は、本発明の目的を阻害しない範囲で特に限定されず、種々の有機基から選択できる。R6として好適な基の具体例としては、炭素数1〜20のアルキル基、置換基を有してもよいフェニル基、置換基を有してもよいナフチル基、及び置換基を有してもよいヘテロシクリル基が挙げられる。R6として、これらの基の中では置換基を有してもよいフェニル基がより好ましく、2−メチルフェニル基が特に好ましい。 R 6 in formula (3) is not particularly limited as long as the object of the present invention is not impaired, and can be selected from various organic groups. Specific examples of suitable groups as R 6 include an alkyl group having 1 to 20 carbon atoms, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, and a substituent. Or a heterocyclyl group that may be used. Among these groups, R 6 is more preferably a phenyl group which may have a substituent, and particularly preferably a 2-methylphenyl group.
R4、R5、又はR6に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合の置換基としては、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数2〜7の飽和脂肪族アシル基、炭素数2〜7のアルコキシカルボニル基、炭素数2〜7の飽和脂肪族アシルオキシ基、炭素数1〜6のアルキル基を有するモノアルキルアミノ基、炭素数1〜6のアルキル基を有するジアルキルアミノ基、モルホリン−1−イル基、ピペラジン−1−イル基、ハロゲン、ニトロ基、及びシアノ基等が挙げられる。R4、R5、又はR6に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合、その置換基の数は、本発明の目的を阻害しない範囲で限定されないが、1〜4が好ましい。R4、R5、又はR6に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基が、複数の置換基を有する場合、複数の置換基は、同一であっても異なっていてもよい。 As the substituent in the case where the phenyl group, naphthyl group, and heterocyclyl group included in R 4 , R 5 , or R 6 further have a substituent, the alkyl group having 1 to 6 carbon atoms, Monoalkylamino having an alkoxy group, a saturated aliphatic acyl group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, and an alkyl group having 1 to 6 carbon atoms Group, a dialkylamino group having an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, and a cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in R 4 , R 5 , or R 6 further have a substituent, the number of the substituent is not limited as long as the object of the present invention is not impaired, 1-4 are preferable. When the phenyl group, naphthyl group, and heterocyclyl group contained in R 4 , R 5 , or R 6 have a plurality of substituents, the plurality of substituents may be the same or different.
式(1)におけるR3は、水素原子、又は炭素数1〜6のアルキル基である。R3としては、メチル基、又はエチル基が好ましく、メチル基がより好ましい。R3がメチル基である場合、式(1)で表される化合物からなる光重合開始剤は、特に感度に優れる。 R 3 in Formula (1) is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 3 is preferably a methyl group or an ethyl group, and more preferably a methyl group. When R 3 is a methyl group, the photopolymerization initiator composed of the compound represented by formula (1) is particularly excellent in sensitivity.
式(1)で表されるオキシムエステル化合物は、pが0である場合、例えば、下記スキーム1に従って合成することができる。具体的には、下記式(1−1)で表される芳香族化合物を、下記式(1−2)で表されるハロカルボニル化合物を用いて、フリーデルクラフツ反応によりアシル化して、下記式(1−3)で表されるケトン化合物を得、得られたケトン化合物(1−3)を、ヒドロキシルアミンによりオキシム化して下記式(1−4)で表されるオキシム化合物を得、次いで式(1−4)のオキシム化合物と、下記式(1−5)で表される酸無水物((R3CO)2O)、又は下記式(1−6)で表される酸ハライド(R3COHal、Halはハロゲン。)とを反応させて、下記式(1−7)で表されるオキシムエステル化合物を得ることができる。なお、下記式(1−2)において、Halはハロゲンであり、下記式(1−1)、(1−2)、(1−3)、(1−4)、及び(1−7)において、R1、R2、R3、及びmは、式(1)と同様である。 When p is 0, the oxime ester compound represented by the formula (1) can be synthesized according to the following scheme 1, for example. Specifically, an aromatic compound represented by the following formula (1-1) is acylated by a Friedel-Crafts reaction using a halocarbonyl compound represented by the following formula (1-2). A ketone compound represented by (1-3) is obtained, and the resulting ketone compound (1-3) is oximed with hydroxylamine to obtain an oxime compound represented by the following formula (1-4), and then the formula (1-4) and an oxime compound of the acid anhydride represented by the following formula (1-5) ((R 3 CO ) 2 O), or an acid halide represented by the following formula (1-6) (R 3 COHal, Hal is a halogen.), And an oxime ester compound represented by the following formula (1-7) can be obtained. In the following formula (1-2), Hal is halogen, and in the following formulas (1-1), (1-2), (1-3), (1-4), and (1-7) , R 1 , R 2 , R 3 , and m are the same as in formula (1).
<スキーム1>
式(1)で表されるオキシムエステル化合物は、pが1である場合、例えば、下記スキーム2に従って合成することができる。具体的には、下記式(2−1)で表されるケトン化合物に、塩酸の存在下に下記式(2−2)で表される亜硝酸エステル(RONO、Rは炭素数1〜6のアルキル基。)を反応させて、下記式(2−3)で表されるケトオキシム化合物を得、次いで、下記式(2−3)で表されるケトオキシム化合物と、下記式(2−4)で表される酸無水物((R3CO)2O)、又は下記式(2−5)で表される酸ハライド(R3COHal、Halはハロゲン。)とを反応させて、下記式(2−6)で表されるオキシムエステル化合物を得ることができる。なお、下記式(2−1)、(2−3)、(2−4)、(2−5)、及び(2−6)において、R1、R2、R3、及びmは、式(1)と同様である。 When p is 1, the oxime ester compound represented by the formula (1) can be synthesized, for example, according to the following scheme 2. Specifically, a ketone compound represented by the following formula (2-1), a nitrite ester (RONO, R represented by the following formula (2-2) in the presence of hydrochloric acid, having 1 to 6 carbon atoms) Alkyl group.) To obtain a ketoxime compound represented by the following formula (2-3), and then a ketoxime compound represented by the following formula (2-3) and the following formula (2-4). An acid anhydride represented by (R 3 CO) 2 O) or an acid halide represented by the following formula (2-5) (R 3 COHal, Hal is a halogen) is reacted with the following formula (2 The oxime ester compound represented by -6) can be obtained. In the following formulas (2-1), (2-3), (2-4), (2-5), and (2-6), R 1 , R 2 , R 3 , and m are the formulas Same as (1).
<スキーム2>
また、式(1)で表されるオキシムエステル化合物は、pが1であり、R1がメチル基であって、R1が結合するベンゼン環に結合するメチル基に対して、R1がパラ位に結合する場合、例えば、下記式(2−7)で表される化合物を、スキーム1と同様の方法で、オキシム化、及びアシル化することによって合成することもできる。なお、下記式(2−7)において、R2は、式(1)と同様である。 Further, in the oxime ester compound represented by the formula (1), p is 1, R 1 is a methyl group, and R 1 is a para group with respect to a methyl group bonded to a benzene ring to which R 1 is bonded. In the case of bonding to a position, for example, a compound represented by the following formula (2-7) can also be synthesized by oximation and acylation in the same manner as in Scheme 1. In the following formula (2-7), R 2 is the same as in formula (1).
式(1)で表されるオキシムエステル化合物の中でも特に好適な化合物としては、下記式の化合物が挙げられる。
感放射線性樹脂組成物は、本発明の目的を阻害しない範囲で、必要に応じて、式(1)で表されるオキシムエステル化合物以外の他の光重合開始剤を含んでいてもよい。他の光重合開始剤の具体例としては、1−ヒドロキシシクロヘキシルフェニルケトン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、1−〔4−(2−ヒドロキシエトキシ)フェニル〕−2−ヒドロキシ−2−メチル−1−プロパン−1−オン、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、1−(4−ドデシルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、ビス(4−ジメチルアミノフェニル)ケトン、2−メチル−1−〔4−(メチルチオ)フェニル〕−2−モルフォリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン、エタノン,1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾル−3−イル],1−(o−アセチルオキシム)、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキシド、4−ベンゾイル−4’−メチルジメチルスルフィド、4−ジメチルアミノ安息香酸、4−ジメチルアミノ安息香酸メチル、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸ブチル、4−ジメチルアミノ−2−エチルヘキシル安息香酸、4−ジメチルアミノ−2−イソアミル安息香酸、ベンジル−β−メトキシエチルアセタール、ベンジルジメチルケタール、1−フェニル−1,2−プロパンジオン−2−(o−エトキシカルボニル)オキシム、o−ベンゾイル安息香酸メチル、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジメチルチオキサントン、1−クロロ−4−プロポキシチオキサントン、チオキサンテン、2−クロロチオキサンテン、2,4−ジエチルチオキサンテン、2−メチルチオキサンテン、2−イソプロピルチオキサンテン、2−エチルアントラキノン、オクタメチルアントラキノン、1,2−ベンズアントラキノン、2,3−ジフェニルアントラキノン、アゾビスイソブチロニトリル、ベンゾイルパーオキシド、クメンパーオキシド、2−メルカプトベンゾイミダール、2−メルカプトベンゾオキサゾール、2−メルカプトベンゾチアゾール、2−(o−クロロフェニル)−4,5−ジフェニルイミダゾール二量体、2−(o−クロロフェニル)−4,5−ジ(メトキシフェニル)イミダゾール二量体、2−(o−フルオロフェニル)−4,5−ジフェニルイミダゾール二量体、2−(o−メトキシフェニル)−4,5−ジフェニルイミダゾール二量体、2−(p−メトキシフェニル)−4,5−ジフェニルイミダゾール二量体、2,4,5−トリアリールイミダゾール二量体、ベンゾフェノン、2−クロロベンゾフェノン、4,4’−ビスジメチルアミノベンゾフェノン(すなわち、ミヒラーズケトン)、4,4’−ビスジエチルアミノベンゾフェノン(すなわち、エチルミヒラーズケトン)、4,4’−ジクロロベンゾフェノン、3,3−ジメチル−4−メトキシベンゾフェノン、ベンジル、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾイン−n−ブチルエーテル、ベンゾインイソブチルエーテル、ベンゾインブチルエーテル、アセトフェノン、2,2−ジエトキシアセトフェノン、p−ジメチルアセトフェノン、p−ジメチルアミノプロピオフェノン、ジクロロアセトフェノン、トリクロロアセトフェノン、p−tert−ブチルアセトフェノン、p−ジメチルアミノアセトフェノン、p−tert−ブチルトリクロロアセトフェノン、p−tert−ブチルジクロロアセトフェノン、α,α−ジクロロ−4−フェノキシアセトフェノン、チオキサントン、2−メチルチオキサントン、2−イソプロピルチオキサントン、ジベンゾスベロン、ペンチル−4−ジメチルアミノベンゾエート、9−フェニルアクリジン、1,7−ビス−(9−アクリジニル)ヘプタン、1,5−ビス−(9−アクリジニル)ペンタン、1,3−ビス−(9−アクリジニル)プロパン、p−メトキシトリアジン、2,4,6−トリス(トリクロロメチル)−s−トリアジン、2−メチル−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(5−メチルフラン−2−イル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(フラン−2−イル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(4−ジエチルアミノ−2−メチルフェニル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(3,4−ジメトキシフェニル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−メトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−エトキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−n−ブトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2,4−ビス−トリクロロメチル−6−(3−ブロモ−4−メトキシ)フェニル−s−トリアジン、2,4−ビス−トリクロロメチル−6−(2−ブロモ−4−メトキシ)フェニル−s−トリアジン、2,4−ビス−トリクロロメチル−6−(3−ブロモ−4−メトキシ)スチリルフェニル−s−トリアジン、2,4−ビス−トリクロロメチル−6−(2−ブロモ−4−メトキシ)スチリルフェニル−s−トリアジン等が挙げられる。これらの中でも、オキシム系の光重合開始剤を用いることが、感度の面で特に好ましい。これらの光重合開始剤は、単独又は2種以上組み合わせて用いることができる。 The radiation-sensitive resin composition may contain other photopolymerization initiator other than the oxime ester compound represented by the formula (1) as necessary, as long as the object of the present invention is not impaired. Specific examples of other photopolymerization initiators include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- [4- (2-hydroxyethoxy) phenyl]- 2-hydroxy-2-methyl-1-propan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy 2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethane-1-one, bis (4-dimethylaminophenyl) ketone, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, eta 1,1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl], 1- (o-acetyloxime), 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 4- Benzoyl-4'-methyldimethylsulfide, 4-dimethylaminobenzoic acid, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 4-dimethylamino-2-ethylhexylbenzoic acid 4-dimethylamino-2-isoamylbenzoic acid, benzyl-β-methoxyethyl acetal, benzyldimethyl ketal, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime, o-benzoylbenzoic acid Methyl, 2,4-diethylthioxanthone, 2-chlorothioxone Sandone, 2,4-dimethylthioxanthone, 1-chloro-4-propoxythioxanthone, thioxanthene, 2-chlorothioxanthene, 2,4-diethylthioxanthene, 2-methylthioxanthene, 2-isopropylthioxanthene, 2-ethylanthraquinone , Octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-diphenylanthraquinone, azobisisobutyronitrile, benzoyl peroxide, cumene peroxide, 2-mercaptobenzoimidar, 2-mercaptobenzoxazole, 2-mercapto Benzothiazole, 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 2- (o-chlorophenyl) -4,5-di (methoxyphenyl) imidazole dimer, 2- (o-fluoro Enyl) -4,5-diphenylimidazole dimer, 2- (o-methoxyphenyl) -4,5-diphenylimidazole dimer, 2- (p-methoxyphenyl) -4,5-diphenylimidazole dimer 2,4,5-triarylimidazole dimer, benzophenone, 2-chlorobenzophenone, 4,4′-bisdimethylaminobenzophenone (ie, Michler's ketone), 4,4′-bisdiethylaminobenzophenone (ie, ethyl Michler's) Ketone), 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone, benzyl, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ester Ter, benzoin butyl ether, acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, p-tert-butylacetophenone, p-dimethylaminoacetophenone, p-tert -Butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, α, α-dichloro-4-phenoxyacetophenone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, pentyl-4-dimethylaminobenzoate, 9- Phenylacridine, 1,7-bis- (9-acridinyl) heptane, 1,5-bis- (9-acridinyl) pentane, 1,3-bis- ( -Acridinyl) propane, p-methoxytriazine, 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- ( 5-methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloromethyl) -S-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxyphenyl) Ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4 -Ethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-bis- Trichloromethyl-6- (3-bromo-4-methoxy) phenyl-s-triazine, 2,4-bis-trichloromethyl-6- (2-bromo-4-methoxy) phenyl-s-triazine, 2,4- Bis-trichloromethyl-6- (3-bromo-4-methoxy) styrylphenyl-s-triazine, 2,4-bis-trichloromethyl-6- (2-bromo-4-methoxy) styrylphenyl-s-triazine, etc. Is mentioned. Among these, it is particularly preferable in terms of sensitivity to use an oxime-based photopolymerization initiator. These photopolymerization initiators can be used alone or in combination of two or more.
感放射線性樹脂組成物が、式(1)で表されるオキシムエステル化合物以外の他の光重合開始剤を含む場合、他の光重合性化合物の含有量は、本発明の目的を阻害しない範囲で特に限定されない。この場合、他の光重合開始剤の含有量は、典型的には、感放射線性樹脂組成物に含まれる光重合開始剤の総量に対して、50質量%以下が好ましく、30質量%以下がより好ましく、10質量%以下が特に好ましい。 When the radiation sensitive resin composition contains another photopolymerization initiator other than the oxime ester compound represented by the formula (1), the content of the other photopolymerizable compound does not hinder the object of the present invention. There is no particular limitation. In this case, the content of the other photopolymerization initiator is typically preferably 50% by mass or less, and preferably 30% by mass or less based on the total amount of the photopolymerization initiator contained in the radiation-sensitive resin composition. More preferred is 10% by mass or less.
(C)成分である光重合開始剤の含有量は、感放射線性樹脂組成物の固形分の合計100質量部に対して0.1〜50質量部が好ましく、0.5〜10質量部がより好ましい。上記範囲内の量で(C)成分を用いることにより、感放射性樹脂組成物を放射線により十分に硬化させることができ、透明性に優れる硬化膜を与える感放射性樹脂組成物が得られる。 (C) As for content of the photoinitiator which is a component, 0.1-50 mass parts is preferable with respect to a total of 100 mass parts of solid content of a radiation sensitive resin composition, and 0.5-10 mass parts is More preferred. By using the component (C) in an amount within the above range, the radiation sensitive resin composition can be sufficiently cured by radiation, and a radiation sensitive resin composition giving a cured film having excellent transparency can be obtained.
<(S)溶剤>
本発明に係る感放射線性樹脂組成物は、塗布性の改善や、粘度調整のため、(S)有機溶剤(以下、「(S)成分」ともいう。)を含むことが好ましい。
<(S) Solvent>
The radiation-sensitive resin composition according to the present invention preferably contains (S) an organic solvent (hereinafter also referred to as “component (S)”) for improving coating properties and adjusting viscosity.
有機溶剤として具体的には、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノ−n−プロピルエーテル、ジエチレングリコールモノ−n−ブチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノ−n−プロピルエーテル、プロピレングリコールモノ−n−ブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノ−n−プロピルエーテル、ジプロピレングリコールモノ−n−ブチルエーテル、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル等の(ポリ)アルキレングリコールモノアルキルエーテル類;エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、プロピレングリコールモノエチルエーテルアセテート等の(ポリ)アルキレングリコールモノアルキルエーテルアセテート類;ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジエチルエーテル、テトラヒドロフラン等の他のエーテル類;メチルエチルケトン、シクロヘキサノン、2−ヘプタノン、3−ヘプタノン等のケトン類;2−ヒドロキシプロピオン酸メチル、2−ヒドロキシプロピオン酸エチル等の乳酸アルキルエステル類;2−ヒドロキシ−2−メチルプロピオン酸エチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、エトキシ酢酸エチル、ヒドロキシ酢酸エチル、2−ヒドロキシ−3−メチルブタン酸メチル、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート、3−メチル−3−メトキシブチルプロピオネート、酢酸エチル、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、蟻酸n−ペンチル、酢酸i−ペンチル、プロピオン酸n−ブチル、酪酸エチル、酪酸n−プロピル、酪酸i−プロピル、酪酸n−ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸n−プロピル、アセト酢酸メチル、アセト酢酸エチル、2−オキソブタン酸エチル等の他のエステル類;トルエン、キシレン等の芳香族炭化水素類;N−メチルピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド等のアミド類;等が挙げられる。これらの中でも、アルキレングリコールモノアルキルエーテル類、アルキレングリコールモノアルキルエーテルアセテート類、上述した他のエーテル類、乳酸アルキルエステル類、上述した他のエステル類が好ましく、アルキレングリコールモノアルキルエーテルアセテート類、上述した他のエーテル類、上述した他のエステル類がより好ましい。これらの溶剤は、単独又は2種以上組み合わせて用いることができる。 Specific examples of the organic solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n- Propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether , Dipropylene glycol monomethyl ether, (Poly) alkylene glycol monoalkyl ethers such as propylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether; ethylene (Poly) alkylene glycol monoalkyl ether acetates such as glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monoethyl ether acetate Diethylene Other ethers such as recall dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone; methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, etc. Alkyl 2-lactic acid esters; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, hydroxy Ethyl acetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3- Methoxybutyl propionate, ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, n-butyl propionate, ethyl butyrate, n-butyrate Other esters such as -propyl, i-propyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate; toluene, xylene Aromatic hydrocarbons such as N-methylpyrrolidone, N, N-dimethylformamide, amides such as N, N-dimethylacetamide, and the like. Among these, alkylene glycol monoalkyl ethers, alkylene glycol monoalkyl ether acetates, other ethers described above, alkyl lactate esters, and other esters described above are preferable, alkylene glycol monoalkyl ether acetates described above. Other ethers and other esters described above are more preferred. These solvents can be used alone or in combination of two or more.
感放射線性樹脂組成物中の(S)成分の含有量は、特に限定されず、感放射線性樹脂組成物を基板等に塗布可能な範囲内の量で、塗布膜厚に応じて適宜設定される。感放射線性樹脂組成物の粘度は0.9〜500cpが好ましく、1〜50cpがより好ましく、1〜30cpがさらに好ましい。また、感放射線性樹脂組成物の固形分濃度は1〜80質量%が好ましく、5〜50質量%がより好ましい。 The content of the component (S) in the radiation-sensitive resin composition is not particularly limited, and is an amount within a range in which the radiation-sensitive resin composition can be applied to a substrate or the like, and is appropriately set according to the coating film thickness. The The viscosity of the radiation sensitive resin composition is preferably 0.9 to 500 cp, more preferably 1 to 50 cp, and further preferably 1 to 30 cp. Moreover, 1-80 mass% is preferable and, as for the solid content density | concentration of a radiation sensitive resin composition, 5-50 mass% is more preferable.
<その他の成分>
本発明に係る感放射線性樹脂組成物には、必要に応じて、界面活性剤、密着性向上剤、熱重合禁止剤、消泡剤等の添加剤を含有させることができる。いずれの添加剤も、従来公知のものを用いることができる。界面活性剤としては、アニオン系、カチオン系、ノニオン系等の化合物が挙げられ、密着性向上剤としては、従来公知のシランカップリング剤が挙げられ、熱重合禁止剤としては、ヒドロキノン、ヒドロキノンモノエチルエーテル等が挙げられ、消泡剤としては、シリコーン系、フッ素系化合物等が挙げられる。
<Other ingredients>
The radiation-sensitive resin composition according to the present invention may contain additives such as a surfactant, an adhesion improver, a thermal polymerization inhibitor, and an antifoaming agent as necessary. Any additive can be used as the additive. Examples of the surfactant include anionic, cationic, and nonionic compounds, examples of the adhesion improver include conventionally known silane coupling agents, and examples of the thermal polymerization inhibitor include hydroquinone and hydroquinone mono Examples of the antifoaming agent include silicone-based and fluorine-based compounds.
<感放射線性樹脂組成物の調製方法>
本発明に係る感放射線性樹脂組成物は、上記各成分をマグネチックスターラーを用いて攪拌、混合溶解し、必要に応じて0.2μmメンブランフィルタ等のフィルタで濾過して調製することができる。
<Method for preparing radiation-sensitive resin composition>
The radiation-sensitive resin composition according to the present invention can be prepared by stirring, mixing and dissolving the above components using a magnetic stirrer, and filtering with a filter such as a 0.2 μm membrane filter as necessary.
≪絶縁膜≫
本発明に係る絶縁膜は、上述の感放射線性樹脂組成物を用いることの他は、感放射線性樹脂組成物を用いて形成された従来の絶縁膜と同様である。以下では絶縁膜の形成方法についてのみ説明する。
≪Insulating film≫
The insulating film according to the present invention is the same as the conventional insulating film formed using the radiation-sensitive resin composition except that the above-described radiation-sensitive resin composition is used. Only the method for forming the insulating film will be described below.
上述の感放射線性樹脂組成物を用いて、絶縁膜を形成する方法は特に制限されず、従来より採用されている方法から適宜選択できる。好適な絶縁膜の形成方法としては、上述の感放射線性樹脂組成物を基板上に塗布し、感放射線性樹脂層を形成する塗布工程と、感放射線性樹脂層を所定の絶縁膜のパターンに応じて露光する露光工程と、露光された感放射線性樹脂層を現像して、絶縁膜のパターンを形成する現像工程と、を含む方法が挙げられる。 The method for forming the insulating film using the above-described radiation-sensitive resin composition is not particularly limited, and can be appropriately selected from conventionally employed methods. As a suitable insulating film forming method, the radiation sensitive resin composition described above is applied on a substrate to form a radiation sensitive resin layer, and the radiation sensitive resin layer is formed into a predetermined insulating film pattern. A method including an exposure step of exposing in response and a development step of developing the exposed radiation-sensitive resin layer to form a pattern of an insulating film is included.
まず、塗布工程では、絶縁膜が形成されるべき基板上に、ロールコーター、リバースコーター、バーコーター等の接触転写型塗布装置やスピンナー(回転式塗布装置)、カーテンフローコーター等の非接触型塗布装置を用いて本発明に係る感放射線性樹脂組成物を塗布し、必要に応じて、乾燥により溶媒を除去して、感放射線性樹脂層を形成する。 First, in the coating process, a contact transfer type coating device such as a roll coater, reverse coater, and bar coater, a non-contact type coating such as a spinner (rotary coating device), a curtain flow coater, etc. is applied on a substrate on which an insulating film is to be formed. The radiation-sensitive resin composition according to the present invention is applied using an apparatus, and if necessary, the solvent is removed by drying to form a radiation-sensitive resin layer.
次いで、表面に感放射線性樹脂層が形成された基板は、露光工程に供される。露光工程では、ネガ型のマスクを介して、感放射線性樹脂層にArFエキシマレーザー、KrFエキシマレーザー、F2エキシマレーザー、極紫外線(EUV)、真空紫外線(VUV)、電子線、X線、軟X線等の放射線を照射し、感放射線性樹脂層を所定の絶縁膜のパターンに応じて部分的に露光する。露光量は感放射線性樹脂組成物の組成によっても異なるが、例えば10〜600mJ/cm2程度が好ましい。 Next, the substrate having the radiation-sensitive resin layer formed on the surface is subjected to an exposure process. In the exposure process, an ArF excimer laser, KrF excimer laser, F 2 excimer laser, extreme ultraviolet (EUV), vacuum ultraviolet (VUV), electron beam, X-ray, softening are applied to the radiation sensitive resin layer through a negative mask. Radiation such as X-rays is irradiated, and the radiation-sensitive resin layer is partially exposed in accordance with a predetermined insulating film pattern. The amount of exposure varies depending on the composition of the radiation-sensitive resin composition, but is preferably about 10 to 600 mJ / cm 2 , for example.
前述の感放射線性樹脂組成物は、露光後にアルカリ現像液に対して過度に溶解しにくい。このため、前述の感放射線性樹脂組成物を用いることにより、露光部を凸部とし、未露光部を凹部とするパターンを良好な形状のパターンとして形成しやすい。 The above-mentioned radiation sensitive resin composition is hardly dissolved in an alkali developer after exposure. For this reason, by using the above-mentioned radiation sensitive resin composition, it is easy to form a pattern having an exposed portion as a convex portion and an unexposed portion as a concave portion as a good shape pattern.
現像工程では、露光後の感放射線性樹脂層を現像液で現像することにより、所定のパターンの絶縁膜を形成する。現像方法は特に限定されず、浸漬法、スプレー法等を用いることができる。現像液の具体例としては、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等の有機系のものや、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、アンモニア、4級アンモニウム塩等の水溶液が挙げられる。 In the development step, the radiation-sensitive resin layer after exposure is developed with a developer to form an insulating film having a predetermined pattern. The development method is not particularly limited, and an immersion method, a spray method, or the like can be used. Specific examples of the developer include organic ones such as monoethanolamine, diethanolamine, and triethanolamine, and aqueous solutions such as sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and quaternary ammonium salts.
そして、必要に応じ、現像後の絶縁膜のパターンにポストベークを施して加熱硬化する。ポストベークの温度は150〜270℃が好ましい。 If necessary, the developed insulating film pattern is post-baked and cured by heating. The post-baking temperature is preferably 150 to 270 ° C.
前述の感放射線性樹脂組成物を用いて形成される絶縁膜は、透明性に優れるため、インセルタッチパネル方式の液晶表示装置、UHA(Ultra High Aperture)パネル等の透明性に優れる絶縁膜を必要とする表示装置用の絶縁膜として好適に使用される。 Since the insulating film formed using the above-mentioned radiation-sensitive resin composition is excellent in transparency, an insulating film excellent in transparency such as an in-cell touch panel type liquid crystal display device, UHA (Ultra High Aperture) panel is required. It is suitably used as an insulating film for a display device.
以下、本発明を実施例によりさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.
〔実施例1〜24、及び比較例1〜5〕
表1に記載の単位から構成されるアルカリ可溶性樹脂15質量部と、光重合性化合物7質量部と、光重合開始剤0.5質量部と、表面調整剤(BYK−310、ポリエステル変性ポリジメチルシロキサン、ビックケミー・ジャパン株式会社製)0.5質量部と、プロピレングリコールモノメチルエーテルアセテート15質量部と、ジエチレングリコールモノメチルエーテル35質量部とを、混合して均一な溶液とし、実施例1〜24、及び比較例1〜5の、感放射線性樹脂組成物を調製した。
[Examples 1 to 24 and Comparative Examples 1 to 5]
15 parts by mass of an alkali-soluble resin composed of the units shown in Table 1, 7 parts by mass of a photopolymerizable compound, 0.5 parts by mass of a photopolymerization initiator, and a surface conditioner (BYK-310, polyester-modified polydimethyl Siloxane, manufactured by Big Chemie Japan Co., Ltd.) 0.5 parts by mass, 15 parts by mass of propylene glycol monomethyl ether acetate, and 35 parts by mass of diethylene glycol monomethyl ether were mixed to obtain a uniform solution, Examples 1 to 24, and Radiation sensitive resin compositions of Comparative Examples 1 to 5 were prepared.
表2に記載のアルカリ可溶性樹脂を構成する単位I〜VIIは、下式で表される単位である。
光重合性化合物としては、2,4,6−トリオキソヘキサヒドロ−1,3,5−トリアジン−1,3,5−トリスエタノールトリアクリレート、及び2,4,6−トリオキソヘキサヒドロ−1,3,5−トリアジン−1,3,5−トリスエタノールジアクリレートの混合物である、M315(東亞合成株式会社製)を用いた。 Examples of the photopolymerizable compound include 2,4,6-trioxohexahydro-1,3,5-triazine-1,3,5-trisethanol triacrylate and 2,4,6-trioxohexahydro-1 , 3,5-triazine-1,3,5-trisethanol diacrylate, M315 (manufactured by Toagosei Co., Ltd.) was used.
光重合開始剤としては、下式で表される化合物を用いた。
実施例1〜24、及び比較例1〜5で得た感放射線性樹脂組成物について、以下の方法に従って、残膜率、耐熱性、及び分離解像性の評価と、ブレークポイント(BP)の測定とを行った。評価結果を表1に記す。 About the radiation sensitive resin composition obtained in Examples 1-24 and Comparative Examples 1-5, according to the following method, evaluation of a residual film rate, heat resistance, and separation resolution, and a breakpoint (BP) Measurement was performed. The evaluation results are shown in Table 1.
(残膜率評価)
ガラス基板に、上記各実施例及び比較例で調製した感放射線性樹脂組成物を、スピンナー(ミカサスピンナーIH−360S、ミカサ株式会社製)でスピン塗布した後、塗膜を100℃で120秒間乾燥させて、感光放射線性樹脂層を形成した。次いで、露光装置(MPA600FA、株式会社キヤノン製)により、露光量100mJ/cm2で、感放射線性樹脂層を露光した。次いで、テトラメチルアンモニウムヒドロキシドの濃度2.38質量%の水溶液を現像液として用い、23℃にて、60秒間パドル現像を行い、パターンを形成した。現像後、パターンを230℃で20分間ポストベークした。ポストベーク後のパターンの膜厚は6μmであった。パターンの膜厚は、触針式表面形状測定器(Dektak 3st、株式会社アルバック製)を用いて測定した。ポストベーク後の膜厚/現像前の膜厚を測定して、残膜率を求めた。残膜率の可否を、以下の基準に従って判定した。
○:80%以上。
×:80%未満。
(Residual film rate evaluation)
After spin-coating the radiation sensitive resin composition prepared in each of the above Examples and Comparative Examples on a glass substrate with a spinner (Mikasa Spinner IH-360S, manufactured by Mikasa Co., Ltd.), the coating film was dried at 100 ° C. for 120 seconds. Thus, a photosensitive radiation-sensitive resin layer was formed. Next, the radiation sensitive resin layer was exposed with an exposure amount of 100 mJ / cm 2 using an exposure apparatus (MPA600FA, manufactured by Canon Inc.). Next, paddle development was performed at 23 ° C. for 60 seconds using an aqueous solution of tetramethylammonium hydroxide having a concentration of 2.38 mass% as a developer to form a pattern. After development, the pattern was post-baked at 230 ° C. for 20 minutes. The film thickness of the pattern after post-baking was 6 μm. The film thickness of the pattern was measured using a stylus type surface shape measuring instrument (Dektak 3st, manufactured by ULVAC, Inc.). The film thickness after post-baking / film thickness before development was measured to determine the remaining film ratio. Whether the remaining film rate was acceptable was determined according to the following criteria.
○: 80% or more.
X: Less than 80%.
(耐熱性評価)
残膜率評価と同様の方法で、現像後の形状のテーパー角が50°以上90°以下であり、ポストベーク後の膜厚が6μmであるパターンを形成した。ポストベーク後のパターンの断面写真から、基板表面と、パターンの表面とがなす角のうち、鋭角であるテーパー角(°)を測定した。テーパー角の測定結果に基づいて、以下の基準に従って、耐熱性を判定した。
○:テーパー角が30〜70°である。
×:テーパー角が30°未満、又は70°超である。
(Heat resistance evaluation)
A pattern having a taper angle of 50 ° or more and 90 ° or less after development and a film thickness after post-baking of 6 μm was formed by the same method as the evaluation of the remaining film rate. From the cross-sectional photograph of the pattern after post-baking, the taper angle (°), which is an acute angle, among the angles formed by the substrate surface and the pattern surface was measured. Based on the measurement result of the taper angle, the heat resistance was determined according to the following criteria.
○: The taper angle is 30 to 70 °.
X: The taper angle is less than 30 ° or more than 70 °.
(分離解像性)
残膜率評価と同様の方法で、露光及び現像を行い、孔径10μmのホールを有するホールパターンを形成した。ポストベーク処理した後、ホールの底部が基板まで達しているか否かを観察した。ホールの観察結果に基づいて、以下の基準に従って、分離解像性を判定した。
○:ホールの底部が基板まで達していた。
×:ホールの底部が基板まで達していなかった。
(Separation resolution)
Exposure and development were performed in the same manner as in the evaluation of the remaining film ratio, and a hole pattern having holes with a hole diameter of 10 μm was formed. After the post-bake treatment, it was observed whether or not the bottom of the hole reached the substrate. Based on the observation results of the holes, the separation resolution was determined according to the following criteria.
○: The bottom of the hole reached the substrate.
X: The bottom of the hole did not reach the substrate.
(ブレークポイントの測定)
Si基板に、上記各実施例及び比較例で調製した感放射線性樹脂組成物を、スピンナー(ミカサスピンナーIH−360S、ミカサ株式会社製)でスピン塗布した後、塗膜を100℃で120秒間乾燥させて、感光放射線性樹脂層を形成した。次いで、露光装置(MPA600FA、株式会社キヤノン製)により、露光量100mJ/cm2で、感放射線性樹脂層を露光した。次いで、テトラメチルアンモニウムヒドロキシドの濃度2.38質量%の水溶液を現像液として用い、23℃にて、60秒間パドル現像を行い、現像液が基板に接した時間からレジスト膜が消失するまでの時間を測定し、ブレークポイントとした。
(Breakpoint measurement)
The radiation sensitive resin composition prepared in each of the above examples and comparative examples was spin-coated on a Si substrate with a spinner (Mikasa Spinner IH-360S, manufactured by Mikasa Co., Ltd.), and then the coating film was dried at 100 ° C. for 120 seconds. Thus, a photosensitive radiation-sensitive resin layer was formed. Next, the radiation sensitive resin layer was exposed with an exposure amount of 100 mJ / cm 2 using an exposure apparatus (MPA600FA, manufactured by Canon Inc.). Next, using an aqueous solution of 2.38% by mass of tetramethylammonium hydroxide as a developing solution, paddle development is performed at 23 ° C. for 60 seconds, and the resist film disappears from the time when the developing solution contacts the substrate. Time was measured and used as a breakpoint.
実施例1〜24と、比較例1〜5とによれば、(a1)不飽和カルボン酸に由来する単位(単位I)と、(a2)エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位(単位II)と、を含む共重合体からなる(A)アルカリ可溶性樹脂と、(B)光重合性化合物と、上記式(1)で表される構造のオキシムエステル化合物を含む(C)光重合開始剤と、を含む感放射線樹脂組成物であれば、露光後の現像時に、露光部が過度に溶解しないことがわかる。 According to Examples 1 to 24 and Comparative Examples 1 to 5, (a1) a unit derived from an unsaturated carboxylic acid (unit I) and (a2) an alicyclic skeleton-containing unsaturated compound having no epoxy group Comprising (A) an alkali-soluble resin, (B) a photopolymerizable compound, and an oxime ester compound having a structure represented by the above formula (1). (C) If it is a radiation sensitive resin composition containing a photoinitiator, it will be understood that an exposed part is not excessively dissolved during development after exposure.
(透明性評価)
実施例11の感放射線性樹脂組成物と、光重合開始剤の種類を除いて実施例11の感光性組成物と同一の組成である、比較例6及び7の感放射線性樹脂組成物とを用いて、感放射線性樹脂組成物を用いて得られる絶縁膜の透明性を評価した。
(Transparency evaluation)
The radiation-sensitive resin composition of Example 11 and the radiation-sensitive resin composition of Comparative Examples 6 and 7 which are the same composition as the photosensitive composition of Example 11 except for the type of photopolymerization initiator. Using, the transparency of the insulating film obtained using a radiation sensitive resin composition was evaluated.
比較例6では、下式で表される光重合開始剤を用いた。
比較例7では、下式で表される光重合開始剤を用いた。
各実施例、及び比較例の感放射線性樹脂組成物を用いて、露光時に選択的に露光を行いことの他は、前述の残膜率の評価方法と同様にして、ポストベークされた感放射線性樹脂組成物の硬化膜を形成した。硬化膜の膜厚は6μmであった。形成された硬化膜の、波長400nmにおける240度透過率を、MCPD−3000(大塚電子(株)製)を用いて測定したところ、実施例11の感放射線性樹脂組成物の硬化膜の透過率は88.8%であり、比較例6の感放射線性樹脂組成物の硬化膜の透過率は76.2%であり、比較例7の感放射線性樹脂組成物の硬化膜の透過率は76.1%であった。 Using the radiation-sensitive resin composition of each example and comparative example, the post-baked radiation-sensitive material was the same as the above-described method for evaluating the remaining film ratio, except that selective exposure was performed during exposure. A cured film of the conductive resin composition was formed. The film thickness of the cured film was 6 μm. When 240 degree transmittance | permeability in wavelength 400nm of the formed cured film was measured using MCPD-3000 (made by Otsuka Electronics Co., Ltd.), the transmittance | permeability of the cured film of the radiation sensitive resin composition of Example 11 was measured. Is 88.8%, the transmittance of the cured film of the radiation sensitive resin composition of Comparative Example 6 is 76.2%, and the transmittance of the cured film of the radiation sensitive resin composition of Comparative Example 7 is 76. It was 1%.
以上の結果より、前述の式(1)で表される化合物を光重合開始剤として含む感放射線性樹脂組成物は、式(1)に含まれない化合物を光重合開始剤として含む感放射線性樹脂組成物よりも、透明性が顕著に優れる絶縁膜を与えることが分かる。 From the above results, the radiation-sensitive resin composition containing the compound represented by the above formula (1) as a photopolymerization initiator is a radiation sensitive resin containing a compound not contained in the formula (1) as a photopolymerization initiator. It can be seen that an insulating film having significantly higher transparency than the resin composition is provided.
Claims (6)
前記(A)アルカリ可溶性樹脂が、(a1)不飽和カルボン酸に由来する単位と、(a2)エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位と、を含み、
前記(C)光重合開始剤が、下記式(1):
mは0〜4の整数であり、
pは0又は1であり、
R2は、置換基を有してもよいフェニル基、又は置換基を有してもよいカルバゾリル基であり、
R3は、水素原子、又は炭素数1〜6のアルキル基であり、
前記カルバゾリル基が有してもよい置換基は、炭素数1〜20のアルキル基、炭素数1〜20のアルコキシ基、炭素数3〜10のシクロアルキル基、炭素数3〜10のシクロアルコキシ基、炭素数2〜20の飽和脂肪族アシル基、炭素数2〜20のアルコキシカルボニル基、炭素数2〜20の飽和脂肪族アシルオキシ基、置換基を有してもよいフェニル基、置換基を有してもよいフェノキシ基、置換基を有してもよいフェニルチオ基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよいベンゾイルオキシ基、置換基を有してもよい炭素数7〜20のフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトキシ基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよいナフトイルオキシ基、置換基を有してもよい炭素数11〜20のナフチルアルキル基、置換基を有してもよいヘテロシクリル基、置換基を有してもよいヘテロシクリルカルボニル基、アミノ基、1、又は2の有機基で置換されたアミノ基、モルホリン−1−イル基、及びピペラジン−1−イル基、ハロゲン、及びシアノ基から選択される基である。)
で表されるオキシムエステル化合物を含み、
前記オキシムエステル化合物は、下記の化合物:
The (A) alkali-soluble resin comprises (a1) a unit derived from an unsaturated carboxylic acid and (a2) a unit derived from an alicyclic skeleton-containing unsaturated compound having no epoxy group,
The (C) photopolymerization initiator is represented by the following formula (1):
m is an integer from 0 to 4,
p is 0 or 1;
R 2 is a phenyl group which may have a substituent, or a carbazolyl group which may have a substituent,
R 3 is Ri hydrogen atom, or an alkyl group der 1 to 6 carbon atoms,
The substituent that the carbazolyl group may have is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or a cycloalkoxy group having 3 to 10 carbon atoms. A saturated aliphatic acyl group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a saturated aliphatic acyloxy group having 2 to 20 carbon atoms, an optionally substituted phenyl group, and a substituent. A phenoxy group which may have a substituent, a phenylthio group which may have a substituent, a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a benzoyl which may have a substituent An oxy group, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a naphthyl group which may have a substituent, a naphthoxy group which may have a substituent, or a substituent. Good naphthoyl group, A naphthoxycarbonyl group which may have a group, a naphthoyloxy group which may have a substituent, a naphthylalkyl group having 11 to 20 carbon atoms which may have a substituent, and a substituent. A good heterocyclyl group, an optionally substituted heterocyclylcarbonyl group, an amino group, an amino group substituted with one or two organic groups, a morpholin-1-yl group, and a piperazin-1-yl group, a halogen, and Ru Ah with a group selected from cyano group. )
An oxime ester compound represented by
The oxime ester compound includes the following compounds:
で表される基、又は下式(3):
で表される基である、請求項1に記載の感放射線性樹脂組成物。 R 2 represents the following formula (2):
Or a group represented by the following formula (3):
The radiation sensitive resin composition of Claim 1 which is group represented by these.
前記(A)アルカリ可溶性樹脂が、(a1)不飽和カルボン酸に由来する単位と、(a2)エポキシ基を持たない脂環式骨格含有不飽和化合物に由来する単位と、を含み、The (A) alkali-soluble resin comprises (a1) a unit derived from an unsaturated carboxylic acid and (a2) a unit derived from an alicyclic skeleton-containing unsaturated compound having no epoxy group,
前記(C)光重合開始剤が、下記式(1):The (C) photopolymerization initiator is represented by the following formula (1):
で表される基、又は下式(3):Or a group represented by the following formula (3):
で表される基であり、RAnd a group represented by R 33 は、水素原子、又は炭素数1〜6のアルキル基である。)Is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. )
で表されるオキシムエステル化合物を含む、感放射線性樹脂組成物。The radiation sensitive resin composition containing the oxime ester compound represented by these.
A display device comprising the insulating film according to claim 5 .
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