JP6302884B2 - 自発光感光性樹脂組成物、これより製造された色変換層を含む表示装置 - Google Patents
自発光感光性樹脂組成物、これより製造された色変換層を含む表示装置 Download PDFInfo
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- JP6302884B2 JP6302884B2 JP2015182180A JP2015182180A JP6302884B2 JP 6302884 B2 JP6302884 B2 JP 6302884B2 JP 2015182180 A JP2015182180 A JP 2015182180A JP 2015182180 A JP2015182180 A JP 2015182180A JP 6302884 B2 JP6302884 B2 JP 6302884B2
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- butyl
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- photosensitive resin
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- 238000006243 chemical reaction Methods 0.000 title claims description 66
- 239000011342 resin composition Substances 0.000 title claims description 46
- -1 laurylthio Chemical group 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229920005989 resin Polymers 0.000 claims description 28
- 239000011347 resin Substances 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 27
- 239000003963 antioxidant agent Substances 0.000 claims description 26
- 239000003999 initiator Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 239000007850 fluorescent dye Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 25
- 230000003078 antioxidant effect Effects 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 230000000977 initiatory effect Effects 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012752 auxiliary agent Substances 0.000 claims description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 6
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000000206 photolithography Methods 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- DNYCICZKXQGHBJ-UHFFFAOYSA-N 2,4-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(C)(C)CC(C)(C)C)=C1 DNYCICZKXQGHBJ-UHFFFAOYSA-N 0.000 claims description 4
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims description 4
- VVNDEUQQZUVMNA-UHFFFAOYSA-N 2,6-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC(C(C)(C)CC(C)(C)C)=C1O VVNDEUQQZUVMNA-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 claims description 4
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 claims description 4
- AESQDCMZHBUWPN-UHFFFAOYSA-N 4h-1,3,2-dioxaphosphinine Chemical compound C1OPOC=C1 AESQDCMZHBUWPN-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003568 thioethers Chemical class 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 4
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 claims description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 claims description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 230000002776 aggregation Effects 0.000 claims description 3
- 238000004220 aggregation Methods 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 235000001671 coumarin Nutrition 0.000 claims description 3
- 229960000956 coumarin Drugs 0.000 claims description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 150000003464 sulfur compounds Chemical class 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- 229940075420 xanthine Drugs 0.000 claims description 3
- GVZIBGFELWPEOC-UHFFFAOYSA-N (2-hydroxy-4-prop-2-enoxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCC=C)=CC=C1C(=O)C1=CC=CC=C1 GVZIBGFELWPEOC-UHFFFAOYSA-N 0.000 claims description 2
- IMNBHNRXUAJVQE-UHFFFAOYSA-N (4-benzoyl-3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound OC1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 IMNBHNRXUAJVQE-UHFFFAOYSA-N 0.000 claims description 2
- LJWQJECMFUGUDV-UHFFFAOYSA-N (4-benzoyl-3-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC(OC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 LJWQJECMFUGUDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical group CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 2
- PLHLRRMUCZBAIP-UHFFFAOYSA-N 2,4-bis(2-methylundecan-2-yl)phenol Chemical compound CCCCCCCCCC(C)(C)C1=CC=C(O)C(C(C)(C)CCCCCCCCC)=C1 PLHLRRMUCZBAIP-UHFFFAOYSA-N 0.000 claims description 2
- KEUMBYCOWGLRBQ-UHFFFAOYSA-N 2,4-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC=C(O)C(C(C)C)=C1 KEUMBYCOWGLRBQ-UHFFFAOYSA-N 0.000 claims description 2
- IGXUCIAXEPFJAX-UHFFFAOYSA-N 2,4-dicyclopentylphenol Chemical compound OC1=CC=C(C2CCCC2)C=C1C1CCCC1 IGXUCIAXEPFJAX-UHFFFAOYSA-N 0.000 claims description 2
- JUXXUMCETXNMIJ-UHFFFAOYSA-N 2,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC(C(C)(C)CC)=C1O JUXXUMCETXNMIJ-UHFFFAOYSA-N 0.000 claims description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 claims description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 2
- BMTAWHXOXODJBS-UHFFFAOYSA-N 2,6-dicyclopentylphenol Chemical compound OC1=C(C2CCCC2)C=CC=C1C1CCCC1 BMTAWHXOXODJBS-UHFFFAOYSA-N 0.000 claims description 2
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 claims description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 claims description 2
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 claims description 2
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 claims description 2
- ZWZHDBGKMXOIIE-UHFFFAOYSA-N 2-butan-2-yl-4-methylphenol Chemical compound CCC(C)C1=CC(C)=CC=C1O ZWZHDBGKMXOIIE-UHFFFAOYSA-N 0.000 claims description 2
- IJYMKBRMIMMBQW-UHFFFAOYSA-N 2-butan-2-yl-6-methylphenol Chemical compound CCC(C)C1=CC=CC(C)=C1O IJYMKBRMIMMBQW-UHFFFAOYSA-N 0.000 claims description 2
- JHEKSKQMOBLXQS-UHFFFAOYSA-N 2-cyclopentylphenol Chemical compound OC1=CC=CC=C1C1CCCC1 JHEKSKQMOBLXQS-UHFFFAOYSA-N 0.000 claims description 2
- IJBSPUKPEDBNKQ-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-prop-1-en-2-ylphenyl)propan-1-one Chemical compound CC(=C)C1=CC=C(C(=O)C(C)(C)O)C=C1 IJBSPUKPEDBNKQ-UHFFFAOYSA-N 0.000 claims description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 2
- DWTBZBLLDLEJMV-UHFFFAOYSA-N 2-methyl-6-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC1=CC=CC(C(C)(C)CC(C)(C)C)=C1O DWTBZBLLDLEJMV-UHFFFAOYSA-N 0.000 claims description 2
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 claims description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 claims description 2
- YLUZWKKWWSCRSR-UHFFFAOYSA-N 3,9-bis(8-methylnonoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCC(C)C)OCC21COP(OCCCCCCCC(C)C)OC2 YLUZWKKWWSCRSR-UHFFFAOYSA-N 0.000 claims description 2
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 claims description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 claims description 2
- ZUEQUQSNOMEMJR-UHFFFAOYSA-N 4-[[3,5-bis[(4-hydroxyphenyl)methyl]phenyl]methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC(CC=2C=CC(O)=CC=2)=CC(CC=2C=CC(O)=CC=2)=C1 ZUEQUQSNOMEMJR-UHFFFAOYSA-N 0.000 claims description 2
- MWJFTXUNWYQEIU-UHFFFAOYSA-N 4-methyl-2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC1=CC=C(O)C(C(C)(C)CC(C)(C)C)=C1 MWJFTXUNWYQEIU-UHFFFAOYSA-N 0.000 claims description 2
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 claims description 2
- ONTIGGPRJSEVGB-UHFFFAOYSA-N 6-decoxybenzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound C1=CC=C2P(OCCCCCCCCCC)(=O)OC3=CC=CC=C3C2=C1 ONTIGGPRJSEVGB-UHFFFAOYSA-N 0.000 claims description 2
- MXFVKYNQQHVOQP-UHFFFAOYSA-N C(CCCCCCC)P(O)(O)OC1=CC=C(C=C1C(C)(C)C)C(C)(C)C Chemical compound C(CCCCCCC)P(O)(O)OC1=CC=C(C=C1C(C)(C)C)C(C)(C)C MXFVKYNQQHVOQP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003508 Dilauryl thiodipropionate Substances 0.000 claims description 2
- 239000002656 Distearyl thiodipropionate Substances 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 2
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- FKIRSCKRJJUCNI-UHFFFAOYSA-N ethyl 7-bromo-1h-indole-2-carboxylate Chemical compound C1=CC(Br)=C2NC(C(=O)OCC)=CC2=C1 FKIRSCKRJJUCNI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- NISZMWZPLJGKCC-UHFFFAOYSA-N lissamine flavine FF free acid Chemical compound C1=CC(C)=CC=C1N(C1=O)C(=O)C2=C3C1=CC=CC3=C(N)C(S(O)(=O)=O)=C2 NISZMWZPLJGKCC-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical class C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Landscapes
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Optical Filters (AREA)
Description
C.I.ソルベントイエロー25、79、81、82、83、89;
C.I.アシッドイエロー7、23、25、42、65、76;
C.I.リアクティブイエロー2、76、116;
C.I.ダイレクトイエロー4、28、44、86、132;
C.I.ディスパルスイエロー54、76;
C.I.ソルベントオレンジ41、54、56、99;
C.I.アシッドオレンジ56、74、95、108、149、162;
C.I.リアクティブオレンジ16;
C.I.ダイレクトオレンジ26;
C.I.ソルベントレッド24、49、90、91、118、119、122、124、125、127、130、132、160、218;
C.I.アシッドレッド73、91、92、97、138、151、211、274、289;
C.I.アシッドバイオレット102;
C.I.ソルベントグリーン1、5;
C.I.アシッドグリーン3、5、9、25、28;
C.I.ベーシックグリーン1;
C.I.バットグリーン1
好ましくは、上記nが1の場合の化合物は、下記化学式2で示すことができる:
a)自発光感光性組成物を基板表面に塗布する段階;
b)プレキュアにより溶媒を乾燥する段階(プリベーク);
c)得られた被膜の上にフォトマスクをつけて活性光線を照射して露光部を硬化させる段階;
d)アルカリ水溶液を用いて未露光部を溶解する現像工程を行う段階;及び
e)乾燥及びポストベークを行う段階を経て得ることができる。
滴下ロートとして、ベンジルマレイミド74.8g(0.20モル)、アクリル酸43.2g(0.30モル)、ビニルトルエン118.0g(0.50モル)、t−ブチルパーオキシ−2−エチルヘキサノエイト4g、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)40gを投入後、撹拌混合して準備し、連鎖移動剤滴下槽として、n−ドデカンチオル6g、PGMEA24gを入れて撹拌混合したものを用意した。
以後、フラスコにPGMEA395gを導入してフラスコ内の雰囲気を空気から窒素にした後、撹拌しながらフラスコの温度を90℃まで昇温した。
引き継いでモノマー及び連鎖移動剤を滴下ロートから滴下を開始した。滴下は、90℃を維持しながら、それぞれ2時間進行して1時間後に110℃に昇温して3時間維持した後、ガス導入管を導入し、酸素/窒素=5/95(v/v)混合ガスのバブリングを開始した。
引き継いで、グリシジルメタクリレート28.4g[(0.10モル)、(本反応に使用したアクリル酸のカルボキシル基に対して33モル%)]、2、2’−メチレンビス(4−メチル−6−t−ブチルフェノール)0.4g、トリエチルアミン0.8gをフラスコ内に投入して110℃で8時間反応を継続し、固形分酸価が70mgKOH/gである樹脂Aを得た。
GPCにより測定したポリスチレン換算の重量平均分子量は、16、000であり、分子量分布(Mw/Mn)は2.3であった。
撹拌機、温度計還流冷却管、滴下ロート及び窒素導入管を具備したフラスコにプロピレングリコールモノメチルエーテルアセテート182gを導入し、フラスコ内の雰囲気を空気から窒素にした後、100℃に昇温後、ベンジルメタクリレート70.5g(0.40モル)、メタクリル酸45.0g(0.50モル)、イソサイクリック骨格のモノメタクリレート44.5g(0.10モル)及びプロピレングリコールモノメチルエーテルアセテート136gを含む混合物にアゾビスイソブチロニトリル3.6gを添加した溶液を滴下ロートから2時間にわたってフラスコに滴下して100℃でさらに5時間撹拌を継続した。
引き継いで、フラスコ内の雰囲気を窒素から空気にして、グリシジルメタクリレート30g[0.2モル、(本反応に使用したメタクリル酸のカルボキシル基に対して40モル%)]、トリスジメチルアミノメチルフェノール0.9g及びヒドロキノン0.145gをフラスコ内に投入して110℃で6時間反応を継続し、固形分酸価が99mgKOH/gである樹脂Bを得た。
GPCにより測定したポリスチレン換算の重量平均分子量は、28、000であり、分子量分布(Mw/Mn)は2.2であった。
撹拌機、温度計還流冷却管、滴下ロート及び窒素導入管を具備したフラスコにプロピレングリコールモノメチルエーテルアセテート182gを導入し、フラスコ内の雰囲気を空気から窒素にした後、100℃に昇温後、ベンジルメタクリレート70.5g(0.40モル)、メタクリル酸45.0g(0.50モル)、2−(2−メチル)アダマンチルメタクリレート22.0g(0.10モル)及びプロピレングリコールモノメチルエーテルアセテート136gを含む混合物にアゾビスイソブチロニトリル3.6gを添加した溶液を滴下ロートから2時間にわたってフラスコに滴下して100℃でさらに5時間撹拌を継続した。
引き継いで、フラスコ内の雰囲気を窒素から空気にして、グリシジルメタクリレート30g[0.2モル、(本反応に使用したメタクリル酸のカルボキシル基に対して40モル%)]、トリスジメチルアミノメチルフェノール0.9g及びヒドロキノン0.145gをフラスコ内に投入して110℃で6時間反応を継続し、固形分酸価が99mgKOH/gである樹脂Cを得た。
GPCにより測定したポリスチレン換算の重量平均分子量は、23、000であり、分子量分布(Mw/Mn)は2.3であった。
上記樹脂の重量平均分子量(Mw)及び数平均分子量(Mn)の測定に対しては、GPC法を用いて下記条件で行い、その時、得られた各数値の比を分子量分布(Mw/Mn)とした。
装置:HLC−8120GPC(東ソー(株)製造)
コラム:TSK−GELG4000HXL+TSK−GELG2000HXL(直列接続)
コラム温度:40℃
移動相溶剤:テトラヒドロフラン
流速:1.0ml/分
注入量:50μl
検出器:RI
測定試料濃度:0.6質量%(溶剤=テトラヒドロフラン)
較正用標準物質:TSK STANDARD POLYSTYRENE F−40、F−4、F−1、A−2500、A−500(東ソー(株)製造)
混合機に溶剤を添加後、そこに染料、酸化防止剤にアルカリ可溶性樹脂、光重合性化合物、及び光重合開始剤を添加し、撹拌を通じて均一に混合して自発光感光性樹脂組成物を製造した。この時、組成物は下記表1の組成に従う。
上記得られた感光性樹脂組成物をスピンコーティング法でガラス基板の上に塗布した後、加熱板の上に置き、100℃の温度で3分間維持して薄膜を形成させた。
引き継いで上記薄膜の上に紫外線を照射した。この時、紫外線光源は、ウシオ電機(株)製の超高圧水銀ランプ(商品名USH−250D)を用いて大気雰囲気下で40mJ/cm2の露光量(365nm)で光照射し、特別な光学フィルターは使用しなかった。
上記紫外線が照射された薄膜をpH12.5のKOH水溶液現像溶液にスプレー現像機を用いて60秒間現像後、220℃の加熱オーブンで20分間加熱してパターンを製造した。上記において製造された色変換層の厚さは3.0μmで形成した。
1)クマリン6
2)LX−SERIES、現代ケミカル製品
3)オクタデシル−3−(3、5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、BASF製品
4)4、4’−ブチリデン−ビス(6−t−ブチル−3−メチルフェノール)、Sumitomo Chemical社製品
5)2、2−チオ−ジエチレンビス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、BASF製品
6)1、1、3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、Addivant社(旧.Chemtura)製品
7)ペンタエリスリトール−テトラキス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、BASF製品
8)6−[3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロポキシ]−2、4、8、10−テトラ−t−ブチルジベンゾ[d、f][1、3、2]ジオキサホスフェピン、Sumitomo Chemical社製品
9)製造例1で製造された樹脂
10)製造例2で製造された樹脂
11)製造例3で製造された樹脂
12)ジペンタエリスリトールヘキサアクリレート、日本化薬(株)製品
13)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、Ciba Specialty Chemical社製品
14)プロピレングリコールモノメチルエーテルアセテート
2)LX−SERIES、現代ケミカル製品
3)オクタデシル−3−(3、5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、BASF製品
4)4、4’−ブチリデン−ビス(6−t−ブチル−3−メチルフェノール)、Sumitomo Chemical社製品
5)2、2−チオ−ジエチレンビス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、BASF製品
6)1、1、3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、Addivant社(旧.Chemtura)製品
7)ペンタエリスリトール−テトラキス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、BASF製品
8)6−[3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロポキシ]−2、4、8、10−テトラ−t−ブチルジベンゾ[d、f][1、3、2]ジオキサホスフェピン、Sumitomo Chemical社製品
9)製造例1で製造された樹脂
10)製造例2で製造された樹脂
11)製造例3で製造された樹脂
12)ジペンタエリスリトールヘキサアクリレート、日本化薬(株)製品
13)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、Ciba Specialty Chemical社製品
14)プロピレングリコールモノメチルエーテルアセテート
上記実施例及び比較例において得られた色変換層の蛍光效率増加可否を確認するため、量子効率測定器(QE−1000、大塚社製)を用いて発光PLを測定した。得られた結果は下記表3に示し、その時、測定された発光強度が高いほど蛍光效率が高いことを意味する。
また、酸化防止剤と光重合開始剤との含有量比が制御された場合でも蛍光效率の変化が意味ありげに発生することを確認した。
上記実施例及び比較例において得られた組成物で製造されたカラーフィルターを対象にテーパー(taper)性及びパターン直進性を画素表面の形状をSEM(10、000倍率)で観察し、その結果を下記表4に示した。この時、テーパー性及びパターン直進性は下記に従う。
<テーパー性>
○:パターンプロファイル(Pattern profile)良好
X:パターンプロファイル(Pattern profile)不良
<直進性>
○:パターンエッジ(Pattern edge)部の直進性偏差が1μm以下
X:パターンエッジ(Pattern edge)部の直進性偏差が1μm超過
3:色変換層
5:カラーフィルター
Claims (17)
- カラーフィルタ、色変換層、および青色バックライトがこの順番で積層された表示装置に色変換層を形成するための自発光感光性樹脂組成物であって、
ここに前記色変換層はフォトリソグラフィー法によってレッド(R)パターンおよびグリーン(G)パターンに対応する各々のパターンとして形成され、かつ、カラーフィルタのブルー(B)パターンに対応するパターンについては形成されず、
ここに前記自発光感光性樹脂組成物が
色変換層形成のための組成物として、
組成物全体を100重量%として、これを満足するように、
蛍光染料0.1〜10重量%、
酸化防止剤0.1〜10重量%、
アルカリ可溶性樹脂5〜85重量%、
光重合性化合物1〜50重量%、
光重合開始剤0.1〜40重量%、及び
残部として溶剤を含み、
前記自発光感光性樹脂組成物は、酸化防止剤:光重合開始剤を1:1.2〜1:3.9の重量比で含むことを特徴とする、自発光感光性樹脂組成物。 - 前記蛍光染料は、クマリン系、ナフタルイミド系、キナクリドン系、シアニン系、キサンチン系、ピリジン系、低分子発光材料、高分子発光材料及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記酸化防止剤は、
2−[3−(2−H−ベンゾトリアゾール−2−イル)−4−ヒドロキシフェニル]エチルメタクリレート、及び2−[2’−ヒドロキシ−5’−メタクリルオキシエチルフェニル]−2H−ベンゾトリアゾールを含むベンゾトリアゾール系化合物;
4−メタクリルオキシ−2−ヒドロキシベンゾフェノン、4−アクリルオキシ−2−ヒドロキシベンゾフェノン、及び4−アリルオキシ−2−ヒドロキシベンゾフェノンを含むベンゾフェノン系化合物;
テトラキス[メタン−3−(ラウリルチオ)プロピオネート]メタン、ジステアリルチオジプロピオネート、及びジラウリルチオジプロピオネートを含むチオエーテル系化合物;
3、9−ビス[2−〔3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ〕−1、1−ジメチルエトキシ]−2、4、8、10−テトラオクサスピロ[5.5]ウンデカンを含むスピロ環骨格を有するフェノール系化合物;
トリス−(3、5−ジ−t−ブチル−4−ヒドロキシベンジル)−イソシアヌレート、1、3、5−トリス(4−t−ブチル−3−ヒドロキシ−2、6−ジメチルベンジル)−イソシアヌレート、N、N'−ヘキサメチレンビス(3、5−ジ−t−ブチル−4−ヒドロキシ−ヒドロシンナムアミド)、4、6−ビス[(オクチルチオ)メチル]−o−クレゾールを含むその他のフェノール系化合物;
3、9−ビス(2、6−ジ−tert−ブチル−4−メチルフェノキシ)−2、4、8、10−テトラオキサ−3、9−ジホスファスピロ[5.5]ウンデカン、ジイソデシルペンタエリスリトールジフォスファイト、及びビス(2、4−ジ−t−ブチルフェニル)ペンタエリスリトールジフォスファイトのスピロ環骨格を有するフォスファイト化合物;
2、2'−メチレンビス(4、6−ジ−t−ブチル−1−フェニルオキシ)(2−エチルヘキシルオキシ)ホスホラス、6−[3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロポキシ]−2、4、8、10−テトラ−t−ブチルジベンズ[d、f][1、3、2]ジオキサホスフェピン、トリフェニルフォスファイト、ジフェニルイソデシルフォスファイト、フェニルジイソデシルフォスファイト、4、4'−ブチリデン−ビス(3−メチル−6−t−ブチルフェニルジトリデシル)フォスファイト、オクタデシルフォスファイト、トリス(ノニルフェニル)フォスファイト、9、10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイド、10−(3、5−ジ−t−ブチル−4−ヒドロキシベンジル)−9、10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイド、10−デシルオキシ−9、10−ジヒドロ−9−オキサ−10−フォスファフェナントレン−10−オキサイド、トリス(2、4−ジ−t−ブチルフェニル)フォスファイト、サイクリックネオペンタンテトライルビス(2、4−ジ−t−ブチルフェニル)フォスファイト、サイクリックネオペンタンテトライルビス(2、6−ジ−t−ブチルフェニル)フォスファイト、2、2−メチレンビス(4、6−ジ−t−ブチルフェニル)オクチルフォスファイト、トリス(2、4−ジ−t−ブチルフェニル)フォスファイト、テトラキス(2、4−ジ−t−ブチルフェニル)[1、1−ビフェニル]−4、4'−ジイルビスホスホナイト、ビス[2、4−ビス(1、1−ジメチルエチル)−6−メチルフェニル]エチルエステル、及びホスホン酸を含むリン系化合物;
2、2−ビス({3−(ドデシルチオ)プロピオニル]オキシ}メチル)−1、3−プロパンジイル−ビス[3−(ドデシルチオ)プロピオネート]、2−メルカプトベンズイミダゾール、ジラウリル−3、3'−チオジプロピオネート、ジミリスチル−3、3'−チオジプロピオネート、ジステアリル−3、3'−チオジプロピオネート、及びペンタエリスリチル−テトラキス(3−ラウリルチオプロピオネート)を含む硫黄系化合物;及び
これらの組合せからなる群より選択された1種を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。 - 前記酸化防止剤は、ヒンダードヒドロキシフェノール系化合物であることを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記化学式2の化合物は、2−t−ブチルフェノール、2、6−ジ−t−ブチルフェノール、2、4−ジ−t−ブチルフェノール、2−sec−ブチルフェノール、2、6−ジ−sec−ブチルフェノール、2、4−ジ−sec−ブチルフェノール、2、6−ジ−t−ブチル−4−エチルフェノール、2−イソプロピルフェノール、2、6−ジイソプロピルフェノール、2、4−ジイソプロピルフェノール、2−t−オクチルフェノール、2、6−ジ−t−オクチルフェノール、2、4−ジ−t−オクチルフェノール、2−シクロペンチルフェノール、2、6−ジシクロペンチルフェノール、2、4−ジシクロペンチルフェノール、2−t−ブチル−p−クレゾール、2、6−ジ−t−アミルフェノール、2、4−ジ−t−アミルフェノール、6−t−ブチル−o−クレゾール、2、6−ジ−t−ドデシルフェノール、2、4−ジ−t−ドデシルフェノール、2−sec−ブチル−p−クレゾール、2、6−ジ−t−オクチルフェノール、2、4−ジ−t−オクチルフェノール、6−sec−ブチル−o−クレゾール、2−t−オクチル−p−クレゾール、2−t−ドデシル−p−クレゾール、2−t−ブチル−6−イソプロピルフェノール、6−t−オクチル−o−クレゾール、6−t−ドデシル−o−クレゾール、またはオクタデシル−3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネートであり、
前記化学式3の化合物は、4、4'−ブチリデンビス(6−t−ブチル−3−メチルフェノール)、2、2'−メチレンビス(4−メチル−6−t−ブチルフェノール)、4、4'−チオ−ビス(3−メチル−6−t−ブチルフェノール)、1、6−ヘキサンジオール−ビス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、トリエチレングリコール−ビス[3−(3−t−ブチル−5−メチル−4−ヒドロキシフェニル)プロピオネート]、または2、2−チオ−ジエチレンビス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]であり、
前記化学式4の化合物は、1、1、3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1、3、5−トリス(4−ヒドロキシベンジル)ベンゼン、または1、3、5−トリメチル−2、4、6−トリス(3、5−ジ−t−ブチル−4−ヒドロキシベンジル)ベンゼンであり、
前記化学式5の化合物は、ペンタエリスリトール−テトラキス[3−(3、5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート]であることを特徴とする、請求項6に記載の自発光感光性樹脂組成物。 - 前記アルカリ可溶性樹脂は、20〜200(KOHmg/g)の酸価を有することを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記アルカリ可溶性樹脂は、カルボキシル基含有不飽和単量体の重合体、またはこれと共重合可能な不飽和結合を有する単量体との共重合体;及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記カルボキシル基含有不飽和単量体は、不飽和モノカルボキシル酸、不飽和ジカルボキシル酸、不飽和トリカルボキシル酸、及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項9に記載の自発光感光性樹脂組成物。
- 前記共重合の可能な単量体は、芳香族ビニル化合物、不飽和カルボキシル酸エステル化合物、不飽和カルボキシル酸アミノアルキルエステル化合物、不飽和カルボキシル酸グリシジルエステル化合物、カルボキシル酸ビニルエステル化合物、不飽和エーテル類化合物、シアン化ビニル化合物、不飽和イミド類化合物、脂肪族共役ジエン系化合物、分子鎖の末端にモノアクリロイル基またはモノメタクリロイル基を有する巨大単量体、かさ高性単量体及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項9に記載の自発光感光性樹脂組成物。
- 前記光重合性化合物は、ノニルフェニルカルビトールアクリレート、2−ヒドロキシ−3−フェノキシプロピルアクリレート、2−エチルヘキシルカルビトールアクリレート、2−ヒドロキシエチルアクリレート、N−ビニルピロリドン、1、6−ヘキサンジオールジ(メタ)アクリレート、エ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、トリエチレングリコールジ(メタ)アクリレート、ビスフェノールAのビス(アクリロイルオキシエチル)エーテル、3−メチルペンタンジオールジ(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、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、及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記光重合開始剤は、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、ベンジルジメチルケタール、2−ヒドロキシ−1−[4−(2−ヒドロキシエトキシ)フェニル]−2−メチルプロパン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、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、2−ヒドロキシ−2−メチル[4−(1−メチルビニル)フェニル]プロパン−1−オンのオリゴマー及びこれらの組合せからなる群より選択された1種のアセトフェノン系化合物を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記自発光感光性樹脂組成物は、さらにベンゾイン系化合物、ベンゾフェノン系化合物、トリアジン系化合物、硫黄化合物、アントラキノン系化合物、有機過酸化物、チオール類化合物及びこれらの組合せからなる群より選択された1種以上の光重合開始補助剤を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記溶剤は、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アルキルエーテルアセテート類、芳香族炭化水素類、ケトン類、低級及び高級アルコール類、環状エステル類、及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 前記自発光感光性樹脂組成物は、充填剤、他の高分子化合物、顔料分散剤、密着促進剤、紫外線吸収剤、凝集防止剤及びこれらの組合せからなる群より選択された1種を含むことを特徴とする、請求項1に記載の自発光感光性樹脂組成物。
- 基板上部に請求項1〜16のいずれか1項による自発光感光性樹脂組成物で製造された色変換層を含む表示装置。
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