JP2015127748A - ブラックカラムスペーサ用感光性樹脂組成物 - Google Patents
ブラックカラムスペーサ用感光性樹脂組成物 Download PDFInfo
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- JP2015127748A JP2015127748A JP2013272916A JP2013272916A JP2015127748A JP 2015127748 A JP2015127748 A JP 2015127748A JP 2013272916 A JP2013272916 A JP 2013272916A JP 2013272916 A JP2013272916 A JP 2013272916A JP 2015127748 A JP2015127748 A JP 2015127748A
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- photosensitive resin
- resin composition
- black column
- solvent
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 101
- 125000006850 spacer group Chemical group 0.000 title claims abstract description 96
- 229920005989 resin Polymers 0.000 claims abstract description 99
- 239000011347 resin Substances 0.000 claims abstract description 99
- 239000002904 solvent Substances 0.000 claims abstract description 97
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 238000009835 boiling Methods 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000000758 substrate Substances 0.000 claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 239000004925 Acrylic resin Substances 0.000 claims description 19
- 229920000178 Acrylic resin Polymers 0.000 claims description 19
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 claims description 4
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 claims description 4
- MPAGVACEWQNVQO-UHFFFAOYSA-N 3-acetyloxybutyl acetate Chemical compound CC(=O)OC(C)CCOC(C)=O MPAGVACEWQNVQO-UHFFFAOYSA-N 0.000 claims description 4
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 claims description 4
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940116423 propylene glycol diacetate Drugs 0.000 claims description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 4
- DBUMQODMPXCGAY-UHFFFAOYSA-N 2-(2-butan-2-yloxypropoxy)propan-1-ol Chemical compound CCC(C)OC(C)COC(C)CO DBUMQODMPXCGAY-UHFFFAOYSA-N 0.000 claims description 3
- ZMFWEWMHABZQNB-UHFFFAOYSA-N 6-acetyloxyhexyl acetate Chemical compound CC(=O)OCCCCCCOC(C)=O ZMFWEWMHABZQNB-UHFFFAOYSA-N 0.000 claims description 3
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 claims description 2
- FIIFPAUBZGVKCI-UHFFFAOYSA-N 2-(2-pentan-2-yloxyethoxy)ethanol Chemical compound CCCC(C)OCCOCCO FIIFPAUBZGVKCI-UHFFFAOYSA-N 0.000 claims 1
- KVXNKFYSHAUJIA-UHFFFAOYSA-N acetic acid;ethoxyethane Chemical compound CC(O)=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 11
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 description 153
- 125000001424 substituent group Chemical group 0.000 description 90
- 125000004432 carbon atom Chemical group C* 0.000 description 76
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 42
- 125000000217 alkyl group Chemical group 0.000 description 40
- 229920001577 copolymer Polymers 0.000 description 34
- 239000006229 carbon black Substances 0.000 description 31
- 235000019241 carbon black Nutrition 0.000 description 31
- 125000002723 alicyclic group Chemical group 0.000 description 30
- 125000003700 epoxy group Chemical group 0.000 description 27
- 125000000623 heterocyclic group Chemical group 0.000 description 24
- 125000001931 aliphatic group Chemical group 0.000 description 23
- 230000002378 acidificating effect Effects 0.000 description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 18
- 125000001624 naphthyl group Chemical group 0.000 description 18
- 125000000962 organic group Chemical group 0.000 description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 230000001771 impaired effect Effects 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 125000001326 naphthylalkyl group Chemical group 0.000 description 9
- 125000003884 phenylalkyl group Chemical group 0.000 description 9
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000000049 pigment Substances 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
- 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 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 125000004018 acid anhydride group Chemical group 0.000 description 4
- 150000003926 acrylamides Chemical class 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
- 238000011161 development Methods 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 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
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 3
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 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
- 150000001768 cations Chemical class 0.000 description 3
- 238000007334 copolymerization reaction Methods 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
- 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
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 150000002923 oximes Chemical class 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
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 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
- 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
- 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
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- 0 CCC1C2C(C3)(CC4)C34C2C(*OC(C(*2CC2)=C)=O)C1 Chemical compound CCC1C2C(C3)(CC4)C34C2C(*OC(C(*2CC2)=C)=O)C1 0.000 description 2
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- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- RCALDWJXTVCBAZ-UHFFFAOYSA-N oct-1-enylbenzene Chemical compound CCCCCCC=CC1=CC=CC=C1 RCALDWJXTVCBAZ-UHFFFAOYSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000005022 packaging material Substances 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
- 239000002245 particle Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- CYFIHPJVHCCGTF-UHFFFAOYSA-N prop-2-enyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC=C CYFIHPJVHCCGTF-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- ZQMAPKVSTSACQB-UHFFFAOYSA-N prop-2-enyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC=C ZQMAPKVSTSACQB-UHFFFAOYSA-N 0.000 description 1
- HAFZJTKIBGEQKT-UHFFFAOYSA-N prop-2-enyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC=C HAFZJTKIBGEQKT-UHFFFAOYSA-N 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
-
- 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
- G03F7/027—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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Polyesters Or Polycarbonates (AREA)
- Liquid Crystal (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Abstract
【解決手段】アルカリ可溶性樹脂、光重合性化合物、光重合開始剤、遮光剤、及び溶剤を含有するブラックカラムスペーサ用感光性樹脂組成物において、大気圧下における沸点が170℃未満である(L)低沸点溶剤と、大気圧下における沸点が180℃以上である(H)高沸点溶剤とを、それぞれ特定量含有する溶剤を配合する。
【選択図】なし
Description
(S)溶剤が、大気圧下における沸点が170℃未満である(L)低沸点溶剤、及び、大気圧下における沸点が180℃以上である(H)高沸点溶剤を含み、
(S)溶剤中の、(L)低沸点溶剤の含有量が30〜99質量%であり、
(S)溶剤中の、(H)高沸点溶剤の含有量が1〜15質量%である、ブラックカラムスペーサ用感光性樹脂組成物である。
感光性樹脂層を所定のスペーサのパターンに応じて露光する工程と、
露光後の感光性樹脂層を現像してスペーサのパターンを形成する現像工程と、を含むブラックカラムスペーサの形成方法である。
本発明に係るブラックカラムスペーサ用感光性樹脂組成物(以下、単に「感光性樹脂組成物」ともいう。)は、アルカリ可溶性樹脂、光重合性化合物、光重合開始剤、遮光剤、及び溶剤を含有する。溶剤としては、大気圧下における沸点が170℃未満である(L)低沸点溶剤と、大気圧下における沸点が180℃以上である(H)高沸点溶剤とを、それぞれ特定量含有する溶剤を用いる。以下、感光性樹脂組成物に含有される各成分について説明する。
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、濃度0.05質量%のKOH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。
また、上記式(a−1)中、mは、0〜20の整数を示す。
(a3)脂環式基含有不飽和化合物としては、脂環式基を有する不飽和化合物であれば特に限定されない。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、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。これらの(a3)脂環式基含有不飽和化合物は、単独又は2種以上組み合わせて用いることができる。
また、(A2)共重合体が、上記(a2)脂環式エポキシ基含有不飽和化合物由来の構成単位と上記(a4)エポキシ基含有不飽和化合物由来の構成単位とを含有する場合、(A2)共重合体に占める(a2)脂環式エポキシ基含有不飽和化合物由来の構成単位の割合と上記(a4)エポキシ基含有不飽和化合物由来の構成単位の割合との合計は、71質量%以上であることが好ましく、71〜95質量%であることがより好ましく、75〜90質量%であることがさらに好ましい。特に、(A2)共重合体に占める上記(a2)脂環式エポキシ基含有不飽和化合物由来の構成単位の割合が単独で71質量%以上であることが好ましく、71〜80質量%であることがより好ましい。上記(a2)脂環式エポキシ基含有不飽和化合物由来の構成単位の割合を上記の範囲にすることにより、感光性樹脂組成物の経時安定性をより向上させることができる。
また、(A2)共重合体が、(a3)脂環式基含有不飽和化合物由来の構成単位を含有する場合、(A2)共重合体に占める上記(a3)脂環式基含有不飽和化合物由来の構成単位の割合は、1〜30質量%であることが好ましく、5〜20質量%であることがより好ましい。
共重合体(A4)における、(B)光重合性化合物との重合可能部位を有する構成単位の占める割合は、1〜45質量%が好ましく、5〜40質量%がより好ましい。共重合体(A4)がこのような比率で各構成単位を含む場合、基板との密着性に優れるブラックカラムスペーサを形成可能な感光性樹脂組成物を得やすい。
光重合性化合物には、単官能化合物と多官能化合物とがある。
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。
光重合開始剤としては、特に限定されず、従来公知の光重合開始剤を用いることができる。
(D)遮光剤としては、感光性樹脂組成物に従来から配合されていたものを特に制限なく用いることができる。遮光剤としては黒色顔料を用いることが好ましい。黒色顔料としては、有機物、無機物を問わず、カーボンブラック、チタンブラック、銅、鉄、マンガン、コバルト、クロム、ニッケル、亜鉛、カルシウム、銀等の金属酸化物、複合酸化物、金属硫化物、金属硫酸塩、金属炭酸塩等の各種の顔料を挙げることができる。これらの中でも、高い遮光性を有するカーボンブラックを用いることが好ましい。
1)濃硫酸、発煙硫酸、クロロスルホン酸等を用いる直接置換法や、亜硫酸塩、亜硫酸水素塩等を用いる間接置換法により、カーボンブラックにスルホン酸基を導入する方法。
2)アミノ基と酸性基とを有する有機化合物と、カーボンブラックとをジアゾカップリングさせる方法。
3)ハロゲン原子と酸性基とを有する有機化合物と、水酸基を有するカーボンブラックとをウィリアムソンのエーテル化法により反応させる方法。
4)ハロカルボニル基と保護基により保護された酸性基とを有する有機化合物と、水酸基を有するカーボンブラックとを反応させる方法。
5)ハロカルボニル基と保護基により保護された酸性基とを有する有機化合物を用いて、カーボンブラックに対してフリーデルクラフツ反応を行った後、脱保護する方法。
本発明に係る感光性樹脂組成物は、希釈のために(S)溶剤を含有する。(S)溶剤は、大気圧下における沸点が170℃未満である(L)低沸点溶剤と、大気圧下における沸点が180℃以上である(H)高沸点溶剤とを必須に含む。(S)溶剤中の(L)低沸点溶剤の含有量は30〜99質量%であり、(H)高沸点溶剤の含有量は1〜15質量%である。(S)溶剤は、大気圧下における沸点が170℃以上180℃未満である(M)中沸点溶剤を含んでいてもよい。
感光性樹脂組成物は、必要に応じて、各種の添加剤を含有していてもよい。添加剤としては、増感剤、硬化促進剤、充填剤、密着促進剤、酸化防止剤、凝集防止剤、熱重合禁止剤、消泡剤、界面活性剤等が挙げられる。
ブラックカラムスペーサは、前述の感光性樹脂組成物から形成されたことを除き、従来のブラックカラムスペーサと同様である。また、表示装置は、前述の感光性樹脂組成物から形成されたブラックカラムスペーサを備えることを除き、従来の表示装置と同様である。以下では、ブラックカラムスペーサの形成方法についてのみ説明する。
アルカリ可溶性樹脂20質量部と、光重合性化合物(ジペンタエリスリトールヘキサアクリレート)20質量部と、光重合開始剤(OXE−02、BASF社製)10質量部と、カーボン分散液50質量部とを、固形分濃度が15質量%となるように、表1〜4に記載の組成の溶媒中に分散させた。得られた分散液を撹拌機で1時間撹拌して均一に溶解させた。得られた溶液を、孔径5μmのメンブレンフィルタでろ過して、各実施例及び比較例の感光性樹脂組成物を得た。
カルド樹脂(A−1)の合成法は下記の通りである。
まず、500ml四つ口フラスコ中に、ビスフェノールフルオレン型エポキシ樹脂(エポキシ当量235)235g、テトラメチルアンモニウムクロライド110mg、2,6−ジ−tert−ブチル−4−メチルフェノール100mg、及びアクリル酸72.0gを仕込み、これに25ml/分の速度で空気を吹き込みながら90〜100℃で加熱溶解した。次に、溶液が白濁した状態のまま徐々に昇温し、120℃に加熱して完全溶解させた。この際、溶液は次第に透明粘稠になったが、そのまま撹拌を継続した。この間、酸価を測定し、1.0mgKOH/g未満になるまで加熱撹拌を続けた。酸価が目標値に達するまで12時間を要した。そして室温まで冷却し、無色透明で固体状の下記式(a−4)で表されるビスフェノールフルオレン型エポキシアクリレートを得た。
なお、このカルド樹脂(A−1)は、上記式(a−1)で表される樹脂に相当する。
PM:プロピレングリコールモノメチルエーテルアセテート
AN:シクロヘキサノン
CP:シクロペンタノン
MB:3−メトキシブタノール
MA:3−メトキシブチルアセテート
TMU:N,N,N’,N’−テトラメチルウレア
DMM:ジプロピレングリコールジメチルエーテル
CHXA:シクロヘキサノールアセテート
BDDA:1,4−ブタンジオールジアセテート
BDGAC:ジエチレングリコールモノブチルエーテルアセテート
HDDA:1,6−ヘキサンジオールジアセテート
ECL:ε−カプロラクトン
BGDA:1,3−ブチレングリコールジアセテート
EDGAC:ジエチレングリコールモノエチルエーテルアセテート
DPMA:ジプロピレングリコールメチルエーテルアセテート
MBGD:ジエチレングリコールメチルブチルエーテル
GBL:γ−ブチロラクトン
DPMNP:ジプロピレングリコールメチル−n−プロピルエーテル
PGDA:プロピレングリコールジアセテート
以下の方法に従って、各実施例及び比較例の感光性樹脂組成物のハーフトーン特性を評価した。
まず、ガラス基板(10cm×10cm)上に感光性樹脂組成物をスピン塗布した。スピン塗布後、ガラス基板を100℃で120秒間加熱して、膜厚3.0μmの感光性樹脂層を形成した。次いで、ミラープロジェクションアライナー(TME−150RTO、株式会社トプコン製)を用いて、露光量10mJ/cm2、及び露光量100mJ/cm2で、感光性樹脂層を露光した。露光された感光性樹脂層を、26℃の濃度0.04質量%のKOH水溶液で60秒間スプレー現像した。現像された感光性樹脂層を、230℃で30分間ポストベークして、ブラックカラムスペーサを形成した。露光量100mJ/cm2で形成されたブラックカラムスペーサの膜厚HFTと、露光量10mJ/cm2で形成されたブラックカラムスペーサの膜厚HHTとの差ΔH(=HFT−HHT)を求めて、ハーフトーン特性の指標とした。表1〜表4に、各実施例及び比較例の感光性樹脂組成物に関するΔH(Å)の値を記す。ΔHの値が2000Å以上である場合が良好である。
ガラス基板(10cm×10cm)上に感光性樹脂組成物をスピン塗布した。スピン塗布後、ガラス基板を100℃で120秒間加熱して、膜厚3.0μmの感光性樹脂層を形成した。次いで、ミラープロジェクションアライナー(TME−150RTO、株式会社トプコン製)を用いて、露光量100mJ/cm2で、感光性樹脂層を露光した。露光された感光性樹脂層を、26℃の濃度0.04質量%のKOH水溶液で120秒間スプレー現像した。現像された感光性樹脂層を、230℃で20分間ポストベークして、硬化膜を形成した。形成された硬化膜について、膜厚のバラツキを、触針式膜厚測定値器(Dektak)を用いて評価した。具体的には、硬化膜内の5点について膜厚を測定し、膜厚の最大値と最小値との差を膜厚のバラツキ(Å)とした。膜厚のバラツキが、200Å以内である場合が良好である。
アルカリ可溶性樹脂中のカルド樹脂及びアクリル樹脂のそれぞれの含有量(質量%)と溶剤種と各溶剤の含有量(質量%)を表5に記載の比率に変更することの他は、実施例9と同様にして感光性樹脂組成物を得た。得られた感光性樹脂組成物を用いて、実施例9の感光性樹脂組成物と同様に、ハーフトーン特性の指標であるΔHと、膜厚バラツキとを評価した。これらの評価結果を表5に記す。参考のため、実施例9の結果を、表5に記す。
Claims (10)
- (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、(D)遮光剤、及び(S)溶剤を含み、
前記(S)溶剤が、大気圧下における沸点が170℃未満である(L)低沸点溶剤、及び、大気圧下における沸点が180℃以上である(H)高沸点溶剤を含み、
前記(S)溶剤中の、前記(L)低沸点溶剤の含有量が30〜99質量%であり、
前記(S)溶剤中の、前記(H)高沸点溶剤の含有量が1〜15質量%である、ブラックカラムスペーサ用感光性樹脂組成物。 - 前記(H)高沸点溶剤の大気圧下における沸点が、180℃以上300℃以下である、請求項1に記載のブラックカラムスペーサ用感光性樹脂組成物。
- 前記(H)高沸点溶剤が、1,4−ブタンジオールジアセテート、ジエチレングリコールモノ−n−ブチルエーテルアセテート、1,6−ヘキサンジオールジアセテート、ε−カプロラクトン、1,3−ブチレングリコールジアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジプロピレングリコールメチルエーテルアセテート、ジエチレングリコールメチル−n−ブチルエーテル、γ−ブチロラクトン、ジプロピレングリコールメチル−n−プロピルエーテル、及びプロピレングリコールジアセテートからなる群より選択される1種以上である、請求項2に記載のブラックカラムスペーサ用感光性樹脂組成物。
- 前記(L)低沸点溶剤の大気圧下における沸点が、100℃以上170℃未満である、請求項1〜3のいずれか1項に記載のブラックカラムスペーサ用感光性樹脂組成物。
- 前記(L)低沸点溶剤が、プロピレングリコールモノメチルエーテルアセテート、シクロヘキサノン、3−メトキシブタノール、及びシクロペンタノンからなる群より選択される1種以上である、請求項4に記載のブラックカラムスペーサ用感光性樹脂組成物。
- 請求項1〜6のいずれか1項に記載のブラックカラムスペーサ用感光性樹脂組成物から形成されたブラックカラムスペーサ。
- 請求項7に記載のブラックカラムスペーサを備える表示装置。
- 請求項1〜6のいずれか1項に記載のブラックカラムスペーサ用感光性樹脂組成物を基板上に塗布し、感光性樹脂層を形成する塗布工程と、
前記感光性樹脂層を所定のスペーサのパターンに応じて露光する露光工程と、
露光後の感光性樹脂層を現像して、スペーサのパターンを形成する現像工程と、を含むブラックカラムスペーサの形成方法。 - 前記露光工程において、ハーフトーンマスクを介して露光が行われる、請求項9に記載のブラックカラムスペーサの形成方法。
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